#------------------------------------------------------------------------------ #$Date: 2019-06-12 03:25:16 +0300 (Wed, 12 Jun 2019) $ #$Revision: 215852 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/13/1551351.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1551351 loop_ _publ_author_name 'Brueckner, Tobias' 'Dewhurst, Rian David' 'Dellermann, Theresa' 'M\"uller, Marcel' 'Braunschweig, Holger' _publ_section_title ; Mild Synthesis of Diboryldiborenes by Diboration of B-B Triple Bonds ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC02544H _journal_year 2019 _chemical_formula_moiety 'C72 H84 B4 N4 O4' _chemical_formula_sum 'C72 H84 B4 N4 O4' _chemical_formula_weight 1112.67 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-11-29 deposited with the CCDC. 2019-06-10 downloaded from the CCDC. ; _cell_angle_alpha 88.943(2) _cell_angle_beta 84.495(2) _cell_angle_gamma 65.880(2) _cell_formula_units_Z 1 _cell_length_a 10.5163(5) _cell_length_b 12.3887(7) _cell_length_c 13.5117(7) _cell_measurement_reflns_used 9897 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.66 _cell_measurement_theta_min 2.33 _cell_volume 1598.83(15) _computing_cell_refinement 'Saint+ ver. V8.37A (Bruker AXS)' _computing_data_collection 'APEX2 ver. 2014.9 (Bruker AXS)' _computing_data_reduction 'Saint+ ver. V8.37A (Bruker AXS)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'CMOS area detector (Photon II)' _diffrn_detector_area_resol_mean 7.5 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 Quest' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'multi-layer mirror' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0889 _diffrn_reflns_av_unetI/netI 0.0358 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 57838 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 2.156 _diffrn_source 'microfocus sealed tube (Incoatec ImS)' _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.7000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2016/2 (Bruker AXS)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.156 _exptl_crystal_description block _exptl_crystal_F_000 596 _exptl_crystal_size_max 0.703 _exptl_crystal_size_mid 0.483 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.362 _refine_diff_density_min -0.477 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 622 _refine_ls_number_reflns 6531 _refine_ls_number_restraints 1254 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0521 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.6405P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1251 _refine_ls_wR_factor_ref 0.1358 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4945 _reflns_number_total 6531 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc02544h2.cif _cod_data_source_block 2c _cod_database_code 1551351 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; ToBr009.res created by SHELXL-2014/7 TITL test_a.res in P-1 REM Old TITL test in P-1 REM SHELXT solution in P-1 REM R1 0.289, Rweak 0.041, Alpha 0.086, Orientation as input REM Formula found by SHELXT: C38 N6 CELL 0.71073 10.5163 12.3887 13.5117 88.943 84.495 65.880 ZERR 1.000 0.0005 0.0007 0.0007 0.002 0.002 0.002 LATT 1 SFAC C H B N O UNIT 72 84 4 4 4 TEMP -173.150 L.S. 10 BOND $H acta 52 conf shel 999 0.8 LIST 4 FMAP 2 PLAN 40 WGHT 0.057700 0.640500 FVAR 0.70570 0.56289 O1 5 0.465311 0.595419 0.745402 11.00000 0.02957 0.03849 = 0.01927 -0.00423 0.00216 -0.02439 B3 3 0.430914 0.555310 0.657768 11.00000 0.01977 0.02038 = 0.02214 -0.00076 -0.00192 -0.01160 O2 5 0.313169 0.528448 0.685809 11.00000 0.02200 0.03312 = 0.01785 -0.00324 0.00128 -0.01682 B4 3 0.507322 0.540338 0.543158 11.00000 0.01776 0.02175 = 0.01979 -0.00044 -0.00118 -0.01220 C1 1 0.282159 0.548409 0.786407 11.00000 0.02391 0.03088 = 0.01751 -0.00189 0.00006 -0.01383 C5 1 0.373500 0.589434 0.822584 11.00000 0.02657 0.03203 = 0.02160 -0.00213 0.00196 -0.01799 C2 1 0.182226 0.528948 0.847760 11.00000 0.03234 0.05892 = 0.02625 -0.00395 0.00252 -0.03113 AFIX 43 H009 2 0.120119 0.500459 0.822569 11.00000 -1.20000 AFIX 0 C3 1 0.368307 0.613832 0.922177 11.00000 0.03861 0.05510 = 0.02295 -0.00730 -0.00056 -0.03063 AFIX 43 H00A 2 0.430784 0.642356 0.946727 11.00000 -1.20000 AFIX 0 C4 1 0.267019 0.594721 0.985388 11.00000 0.04350 0.06380 = 0.01798 -0.00699 0.00387 -0.03077 AFIX 43 H00B 2 0.260062 0.610549 1.054689 11.00000 -1.20000 AFIX 0 C6 1 0.176298 0.553049 0.948944 11.00000 0.03932 0.07095 = 0.02400 -0.00474 0.00833 -0.03534 AFIX 43 H00I 2 0.108584 0.540627 0.993875 11.00000 -1.20000 AFIX 0 simu 0.005 n1_1 > c24_1 n1_11 > c24_11 rigu 0.003 n1_1 > c24_1 n1_11 > c24_11 Part 1 21 RESI 1 NHC N1 4 0.594834 0.690990 0.457749 21.00000 0.02188 0.02691 = 0.02309 0.00170 -0.00182 -0.01564 N2 4 0.733374 0.573041 0.532819 21.00000 0.02035 0.02734 = 0.02274 0.00283 -0.00279 -0.01570 C1 1 0.619237 0.594739 0.513369 21.00000 0.02206 0.02644 = 0.01361 -0.00189 -0.00075 -0.01663 C2 1 0.838215 0.599156 0.470404 21.00000 0.02423 0.04166 = 0.03268 0.00860 -0.00414 -0.02175 AFIX 23 H2A 2 0.893637 0.535983 0.420386 21.00000 -1.20000 H2AB 2 0.900566 0.620223 0.508974 21.00000 -1.20000 AFIX 0 C3 1 0.725098 0.706136 0.426763 21.00000 0.02688 0.04041 = 0.03543 0.00714 -0.00214 -0.02413 AFIX 23 H3A 2 0.721382 0.781024 0.454213 21.00000 -1.20000 H3AB 2 0.741930 0.705673 0.353384 21.00000 -1.20000 AFIX 0 C4 1 0.460683 0.789434 0.448898 21.00000 0.02807 0.02124 = 0.02795 0.00002 0.00132 -0.01594 C5 1 0.412042 0.815531 0.355357 21.00000 0.02628 0.02356 = 0.03326 0.00278 -0.00051 -0.01353 C6 1 0.264214 0.907662 0.325173 21.00000 0.03400 0.02368 = 0.04051 -0.00003 -0.00786 -0.00890 AFIX 43 H6 2 0.238474 0.913186 0.259158 21.00000 -1.20000 AFIX 0 C7 1 0.176313 0.978991 0.402805 21.00000 0.03453 0.02699 = 0.04569 -0.00012 -0.00608 -0.00454 AFIX 43 H7 2 0.089801 1.041207 0.390212 21.00000 -1.20000 AFIX 0 C8 1 0.214595 0.959514 0.498152 21.00000 0.03328 0.02387 = 0.04046 -0.00543 -0.00024 -0.00664 AFIX 43 H8 2 0.153451 1.009226 0.550741 21.00000 -1.20000 AFIX 0 C9 1 0.340570 0.868932 0.520184 21.00000 0.03158 0.02210 = 0.03043 -0.00025 0.00047 -0.01539 C10 1 0.479785 0.738095 0.260707 21.00000 0.02494 0.02632 = 0.02924 0.00670 -0.00020 -0.01464 AFIX 13 H10 2 0.556609 0.664710 0.282352 21.00000 -1.20000 AFIX 0 C11 1 0.383870 0.698955 0.214489 21.00000 0.02981 0.03599 = 0.03784 0.00206 -0.00613 -0.01599 AFIX 137 H11A 2 0.434430 0.646496 0.157252 21.00000 -1.50000 H11B 2 0.305753 0.768047 0.192312 21.00000 -1.50000 H11C 2 0.347681 0.656307 0.263187 21.00000 -1.50000 AFIX 0 C12 1 0.553163 0.799980 0.184684 21.00000 0.02929 0.03086 = 0.03332 0.00891 -0.00073 -0.01162 AFIX 137 H12A 2 0.609718 0.743506 0.131264 21.00000 -1.50000 H12B 2 0.613521 0.825828 0.219823 21.00000 -1.50000 H12C 2 0.481365 0.868654 0.156226 21.00000 -1.50000 AFIX 0 C13 1 0.380736 0.856113 0.626216 21.00000 0.03803 0.02263 = 0.02877 -0.00279 0.00232 -0.01523 AFIX 13 H13 2 0.458573 0.776324 0.631628 21.00000 -1.20000 AFIX 0 C14 1 0.257934 0.864949 0.702220 21.00000 0.04554 0.03479 = 0.02978 -0.00115 0.00733 -0.01364 AFIX 137 H14A 2 0.290463 0.848206 0.768676 21.00000 -1.50000 H14B 2 0.221655 0.807362 0.684213 21.00000 -1.50000 H14C 2 0.183485 0.944905 0.702168 21.00000 -1.50000 AFIX 0 C15 1 0.433816 0.950468 0.652154 21.00000 0.07417 0.04014 = 0.03668 -0.00265 -0.00325 -0.03761 AFIX 137 H15A 2 0.466451 0.936385 0.718669 21.00000 -1.50000 H15B 2 0.357416 1.029312 0.650945 21.00000 -1.50000 H15C 2 0.511250 0.945560 0.603302 21.00000 -1.50000 AFIX 0 C16 1 0.802162 0.486260 0.604030 21.00000 0.01538 0.02775 = 0.02395 0.00064 -0.00054 -0.01510 C17 1 0.870531 0.366590 0.577706 21.00000 0.01642 0.02934 = 0.02520 0.00033 -0.00256 -0.01517 C18 1 0.943493 0.287986 0.649492 21.00000 0.01907 0.03104 = 0.02959 0.00015 -0.00015 -0.01216 AFIX 43 H18 2 0.987704 0.205781 0.633380 21.00000 -1.20000 AFIX 0 C19 1 0.953052 0.326565 0.743166 21.00000 0.01983 0.03303 = 0.02430 0.00207 -0.00101 -0.01411 C20 1 0.885852 0.446418 0.765311 21.00000 0.02074 0.03430 = 0.02289 0.00172 -0.00146 -0.01627 AFIX 43 H20 2 0.892319 0.474104 0.828936 21.00000 -1.20000 AFIX 0 C21 1 0.809322 0.527954 0.698392 21.00000 0.01804 0.02927 = 0.02381 -0.00071 -0.00086 -0.01531 C22 1 0.737792 0.657615 0.728191 21.00000 0.03056 0.03049 = 0.03477 -0.00551 -0.00451 -0.01561 AFIX 137 H22A 2 0.725431 0.665821 0.800886 21.00000 -1.50000 H22B 2 0.646121 0.692594 0.702030 21.00000 -1.50000 H22C 2 0.795465 0.698463 0.700970 21.00000 -1.50000 AFIX 0 C23 1 0.869499 0.320549 0.476343 21.00000 0.02004 0.03262 = 0.03459 -0.00573 -0.00401 -0.00951 AFIX 137 H23A 2 0.945836 0.241813 0.465377 21.00000 -1.50000 H23B 2 0.882172 0.374267 0.426076 21.00000 -1.50000 H23C 2 0.779814 0.315406 0.471175 21.00000 -1.50000 AFIX 0 C24 1 1.036162 0.239484 0.817268 21.00000 0.03408 0.04754 = 0.03281 0.01071 -0.00470 -0.01565 AFIX 137 H24A 2 1.101127 0.267655 0.843528 21.00000 -1.50000 H24B 2 1.089126 0.162073 0.784262 21.00000 -1.50000 H24C 2 0.972082 0.232302 0.872028 21.00000 -1.50000 AFIX 0 RESI 0 part 0 Part 2 -21 RESI 11 NHC N1 4 0.562522 0.711031 0.457292 -21.00000 0.02149 0.02473 = 0.02161 0.00165 -0.00174 -0.01835 N2 4 0.759295 0.536535 0.524422 -21.00000 0.01701 0.02996 = 0.02308 0.00301 -0.00205 -0.01597 C1 1 0.596417 0.610733 0.511094 -21.00000 0.01790 0.02782 = 0.01798 -0.00303 -0.00520 -0.01262 C2 1 0.679900 0.747406 0.439787 -21.00000 0.01778 0.02478 = 0.03049 0.00281 0.00008 -0.01335 AFIX 23 H2A 2 0.658284 0.823349 0.474677 -21.00000 -1.20000 H2AB 2 0.701831 0.755623 0.367879 -21.00000 -1.20000 AFIX 0 C3 1 0.799629 0.647466 0.482202 -21.00000 0.01761 0.02527 = 0.02948 0.00401 0.00043 -0.01490 AFIX 23 H3A 2 0.830587 0.679309 0.537392 -21.00000 -1.20000 H3AB 2 0.879214 0.615875 0.430015 -21.00000 -1.20000 AFIX 0 C4 1 0.424955 0.795286 0.438926 -21.00000 0.02273 0.02070 = 0.02964 0.00043 -0.00501 -0.01487 C5 1 0.388194 0.815343 0.340975 -21.00000 0.02749 0.02222 = 0.03063 0.00130 -0.00780 -0.01587 C6 1 0.294630 0.919744 0.350234 -21.00000 0.03200 0.02629 = 0.04258 0.00423 -0.00907 -0.01181 AFIX 43 H6 2 0.263892 0.955164 0.289047 -21.00000 -1.20000 AFIX 0 C7 1 0.229351 0.991261 0.432421 -21.00000 0.03436 0.02633 = 0.04928 -0.00132 -0.00320 -0.00786 AFIX 43 H7 2 0.148548 1.062265 0.426319 -21.00000 -1.20000 AFIX 0 C8 1 0.280198 0.960746 0.523448 -21.00000 0.03346 0.02405 = 0.04257 -0.00455 0.00264 -0.01229 AFIX 43 H8 2 0.231777 1.010129 0.579850 -21.00000 -1.20000 AFIX 0 C9 1 0.400207 0.859904 0.535387 -21.00000 0.03227 0.02142 = 0.03430 -0.00252 0.00052 -0.01662 C10 1 0.489004 0.743013 0.256198 -21.00000 0.02493 0.02801 = 0.02975 -0.00174 -0.00754 -0.01363 AFIX 13 H10 2 0.573407 0.679594 0.281467 -21.00000 -1.20000 AFIX 0 C11 1 0.406097 0.686525 0.194238 -21.00000 0.02647 0.03021 = 0.03337 -0.00221 -0.01027 -0.00998 AFIX 137 H11A 2 0.470593 0.633824 0.141287 -21.00000 -1.50000 H11B 2 0.329255 0.750060 0.164852 -21.00000 -1.50000 H11C 2 0.368161 0.641432 0.238999 -21.00000 -1.50000 AFIX 0 C12 1 0.528961 0.818927 0.187995 -21.00000 0.02605 0.03613 = 0.03027 -0.00215 -0.00134 -0.01216 AFIX 137 H12A 2 0.585275 0.772297 0.129309 -21.00000 -1.50000 H12B 2 0.583891 0.852293 0.221404 -21.00000 -1.50000 H12C 2 0.444567 0.883203 0.167444 -21.00000 -1.50000 AFIX 0 C13 1 0.457692 0.835020 0.636278 -21.00000 0.05084 0.02716 = 0.02829 -0.00511 0.00042 -0.01853 AFIX 13 H13 2 0.521500 0.749118 0.636894 -21.00000 -1.20000 AFIX 0 C14 1 0.344167 0.859658 0.722950 -21.00000 0.07582 0.04068 = 0.04260 -0.00156 0.01441 -0.00233 AFIX 137 H14A 2 0.388047 0.830420 0.784445 -21.00000 -1.50000 H14B 2 0.284160 0.819314 0.710068 -21.00000 -1.50000 H14C 2 0.287518 0.945035 0.729898 -21.00000 -1.50000 AFIX 0 C15 1 0.545062 0.905405 0.649911 -21.00000 0.09528 0.04511 = 0.05547 0.00614 -0.02853 -0.04589 AFIX 137 H15A 2 0.577731 0.892204 0.716427 -21.00000 -1.50000 H15B 2 0.487675 0.989831 0.642402 -21.00000 -1.50000 H15C 2 0.625852 0.879354 0.599655 -21.00000 -1.50000 AFIX 0 C16 1 0.824591 0.445231 0.594219 -21.00000 0.01800 0.03076 = 0.02186 0.00385 -0.00364 -0.01473 C17 1 0.879312 0.326504 0.566718 -21.00000 0.01456 0.03112 = 0.03108 0.00102 -0.00004 -0.01392 C18 1 0.953122 0.243123 0.633705 -21.00000 0.01947 0.03646 = 0.03284 0.00448 -0.00358 -0.01154 AFIX 43 H18 2 0.990338 0.161559 0.615455 -21.00000 -1.20000 AFIX 0 C19 1 0.974073 0.275961 0.727098 -21.00000 0.02062 0.03804 = 0.03048 0.00616 -0.00117 -0.01425 C20 1 0.919482 0.393845 0.753212 -21.00000 0.02002 0.03636 = 0.02451 0.00266 -0.00434 -0.01411 AFIX 43 H20 2 0.933122 0.416737 0.816691 -21.00000 -1.20000 AFIX 0 C21 1 0.844096 0.481279 0.688495 -21.00000 0.01946 0.03394 = 0.02730 0.00066 -0.00129 -0.01538 C22 1 0.785026 0.608845 0.721883 -21.00000 0.02670 0.03678 = 0.03113 -0.00115 -0.00621 -0.01647 AFIX 137 H22A 2 0.842525 0.619267 0.770677 -21.00000 -1.50000 H22B 2 0.688896 0.632210 0.752324 -21.00000 -1.50000 H22C 2 0.785128 0.658267 0.664428 -21.00000 -1.50000 AFIX 0 C23 1 0.862707 0.285860 0.467246 -21.00000 0.02066 0.03486 = 0.03261 -0.00192 -0.00386 -0.00887 AFIX 137 H23A 2 0.903987 0.199198 0.463716 -21.00000 -1.50000 H23B 2 0.910271 0.315890 0.415068 -21.00000 -1.50000 H23C 2 0.762973 0.315833 0.457708 -21.00000 -1.50000 AFIX 0 C24 1 1.055848 0.184329 0.799446 -21.00000 0.03820 0.05427 = 0.03937 0.01456 -0.00698 -0.00954 AFIX 137 H24A 2 1.019557 0.213457 0.867776 -21.00000 -1.50000 H24B 2 1.154986 0.170045 0.788754 -21.00000 -1.50000 H24C 2 1.045769 0.110355 0.788495 -21.00000 -1.50000 AFIX 0 RESI 0 PArt 0 part 3 10.5 RESI 3 BEN C1 1 0.290522 0.986567 -0.003544 10.50000 0.07827 AFIX 43 H1 2 0.368600 0.934688 -0.045576 10.50000 -1.20000 AFIX 0 C2 1 0.187356 0.954640 0.029601 10.50000 0.06121 AFIX 43 H2 2 0.188773 0.880780 0.010292 10.50000 -1.20000 AFIX 0 C3 1 0.079255 1.031873 0.092420 10.50000 0.06649 AFIX 43 H3 2 0.009457 1.005947 0.118163 10.50000 -1.20000 AFIX 0 C4 1 0.062106 1.142872 0.121690 10.50000 0.06517 AFIX 43 H4 2 -0.015599 1.193148 0.164903 10.50000 -1.20000 AFIX 0 C5 1 0.166240 1.174805 0.083396 10.50000 0.07285 AFIX 43 H5 2 0.159148 1.252021 0.097470 10.50000 -1.20000 AFIX 0 C6 1 0.281570 1.098017 0.024788 10.50000 0.06692 AFIX 43 H6 2 0.355582 1.120820 0.003426 10.50000 -1.20000 AFIX 0 part 0 RESI 0 part 4 10.5 RESI 13 BEN C1 1 0.242738 1.150382 0.049916 10.50000 0.05089 AFIX 43 H1 2 0.276757 1.210693 0.045690 10.50000 -1.20000 AFIX 0 C2 1 0.262264 0.960412 0.000248 10.50000 0.04749 AFIX 43 H2 2 0.308835 0.890571 -0.039880 10.50000 -1.20000 AFIX 0 C3 1 0.145591 0.972812 0.063961 10.50000 0.05626 AFIX 43 H3 2 0.115384 0.910215 0.069455 10.50000 -1.20000 AFIX 0 C4 1 0.072695 1.076487 0.119803 10.50000 0.06502 AFIX 43 H4 2 -0.009328 1.087210 0.162071 10.50000 -1.20000 AFIX 0 C5 1 0.123839 1.164971 0.111925 10.50000 0.06415 AFIX 43 H5 2 0.075914 1.236362 0.149912 10.50000 -1.20000 AFIX 0 C6 1 0.311210 1.046482 -0.005809 10.50000 0.04747 AFIX 43 H6 2 0.392967 1.035291 -0.048570 10.50000 -1.20000 RESI 0 part 0 AFIX 0 HKLF 4 REM test_a.res in P-1 REM R1 = 0.0521 for 4945 Fo > 4sig(Fo) and 0.0716 for all 6531 data REM 622 parameters refined using 1254 restraints END WGHT 0.0577 0.6405 REM Highest difference peak 0.362, deepest hole -0.477, 1-sigma level 0.041 Q1 1 0.3351 0.9212 -0.0275 11.00000 0.05 0.36 Q2 1 0.3796 1.0380 -0.0067 11.00000 0.05 0.32 Q3 1 0.4840 0.5397 0.6029 11.00000 0.05 0.27 Q4 1 0.0985 1.2337 0.0996 11.00000 0.05 0.23 Q5 1 0.2592 1.0641 0.0002 11.00000 0.05 0.19 Q6 1 0.3154 0.5794 0.8048 11.00000 0.05 0.19 Q7 1 0.3019 1.1225 0.0600 11.00000 0.05 0.18 Q8 1 0.2264 1.0017 0.0278 11.00000 0.05 0.17 Q9 1 0.5000 0.5000 0.5000 10.50000 0.05 0.17 Q10 1 0.2582 0.9752 0.3820 11.00000 0.05 0.16 Q11 1 0.5447 0.5845 0.5311 11.00000 0.05 0.16 Q12 1 0.7206 0.7049 0.6678 11.00000 0.05 0.16 Q13 1 0.9072 0.5638 0.4264 11.00000 0.05 0.16 Q14 1 0.4498 0.7858 0.3071 11.00000 0.05 0.15 Q15 1 0.2605 0.9928 0.4749 11.00000 0.05 0.15 Q16 1 0.0602 1.0397 0.1480 11.00000 0.05 0.14 Q17 1 0.6060 0.8877 0.6282 11.00000 0.05 0.14 Q18 1 1.0256 0.2665 0.8958 11.00000 0.05 0.14 Q19 1 0.1843 1.1271 0.1102 11.00000 0.05 0.14 Q20 1 0.2591 0.9400 0.2450 11.00000 0.05 0.13 Q21 1 0.3995 0.5587 0.8716 11.00000 0.05 0.13 Q22 1 0.1577 0.4353 0.8218 11.00000 0.05 0.13 Q23 1 0.4590 0.7068 0.2290 11.00000 0.05 0.13 Q24 1 0.0419 1.1203 0.1039 11.00000 0.05 0.13 Q25 1 0.8771 0.6327 0.5295 11.00000 0.05 0.13 Q26 1 0.2576 0.5143 0.8223 11.00000 0.05 0.12 Q27 1 0.9927 0.1542 0.8508 11.00000 0.05 0.12 Q28 1 0.4592 0.9780 -0.0817 11.00000 0.05 0.12 Q29 1 0.4126 0.8524 0.4887 11.00000 0.05 0.12 Q30 1 0.0613 0.5929 0.9887 11.00000 0.05 0.12 Q31 1 0.7937 0.6800 0.7731 11.00000 0.05 0.12 Q32 1 0.6193 0.6931 0.7545 11.00000 0.05 0.12 Q33 1 0.7641 0.6569 0.3906 11.00000 0.05 0.12 Q34 1 0.2188 0.5596 0.8144 11.00000 0.05 0.12 Q35 1 0.1930 1.1762 0.0348 11.00000 0.05 0.12 Q36 1 0.3556 0.5529 0.9483 11.00000 0.05 0.11 Q37 1 0.4291 0.8463 -0.0627 11.00000 0.05 0.11 Q38 1 0.1433 0.4776 1.0009 11.00000 0.05 0.11 Q39 1 0.3031 0.5528 1.0671 11.00000 0.05 0.11 Q40 1 0.7784 0.6504 0.4196 11.00000 0.05 0.11 ; _shelx_res_checksum 86250 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.46531(11) 0.59542(10) 0.74540(7) 0.0259(3) Uani 1 1 d . . . . . B3 B 0.43091(17) 0.55531(14) 0.65777(12) 0.0196(3) Uani 1 1 d . . . . . O2 O 0.31317(10) 0.52845(9) 0.68581(7) 0.0227(2) Uani 1 1 d . . . . . B4 B 0.50732(17) 0.54034(14) 0.54316(12) 0.0184(3) Uani 1 1 d . . . . . C1 C 0.28216(16) 0.54841(14) 0.78641(11) 0.0233(3) Uani 1 1 d . . . . . C5 C 0.37350(16) 0.58943(14) 0.82258(11) 0.0250(3) Uani 1 1 d . . . . . C2 C 0.18223(18) 0.52895(17) 0.84776(12) 0.0354(4) Uani 1 1 d . . . . . H009 H 0.1201 0.5005 0.8226 0.042 Uiso 1 1 calc R U . . . C3 C 0.36831(19) 0.61383(17) 0.92218(12) 0.0352(4) Uani 1 1 d . . . . . H00A H 0.4308 0.6424 0.9467 0.042 Uiso 1 1 calc R U . . . C4 C 0.2670(2) 0.59472(19) 0.98539(12) 0.0392(4) Uani 1 1 d . . . . . H00B H 0.2601 0.6105 1.0547 0.047 Uiso 1 1 calc R U . . . C6 C 0.1763(2) 0.55305(19) 0.94894(13) 0.0413(5) Uani 1 1 d . . . . . H00I H 0.1086 0.5406 0.9939 0.050 Uiso 1 1 calc R U . . . N1_1 N 0.5948(5) 0.6910(5) 0.4577(5) 0.0221(8) Uani 0.563(3) 1 d . U P A 1 N2_1 N 0.7334(5) 0.5730(3) 0.5328(4) 0.0215(7) Uani 0.563(3) 1 d . U P A 1 C1_1 C 0.6192(8) 0.5947(7) 0.5134(8) 0.0185(9) Uani 0.563(3) 1 d . U P A 1 C2_1 C 0.8382(4) 0.5992(4) 0.4704(3) 0.0301(8) Uani 0.563(3) 1 d . U P A 1 H2A_1 H 0.8936 0.5360 0.4204 0.036 Uiso 0.563(3) 1 calc R U P A 1 H2AB_1 H 0.9006 0.6202 0.5090 0.036 Uiso 0.563(3) 1 calc R U P A 1 C3_1 C 0.7251(4) 0.7061(4) 0.4268(3) 0.0310(8) Uani 0.563(3) 1 d . U P A 1 H3A_1 H 0.7214 0.7810 0.4542 0.037 Uiso 0.563(3) 1 calc R U P A 1 H3AB_1 H 0.7419 0.7057 0.3534 0.037 Uiso 0.563(3) 1 calc R U P A 1 C4_1 C 0.4607(5) 0.7894(6) 0.4489(4) 0.0241(8) Uani 0.563(3) 1 d . U P A 1 C5_1 C 0.4120(6) 0.8155(7) 0.3554(5) 0.0268(9) Uani 0.563(3) 1 d . U P A 1 C6_1 C 0.2642(5) 0.9077(4) 0.3252(3) 0.0334(8) Uani 0.563(3) 1 d . U P A 1 H6_1 H 0.2385 0.9132 0.2592 0.040 Uiso 0.563(3) 1 calc R U P A 1 C7_1 C 0.1763(4) 0.9790(3) 0.4028(3) 0.0382(7) Uani 0.563(3) 1 d . U P A 1 H7_1 H 0.0898 1.0412 0.3902 0.046 Uiso 0.563(3) 1 calc R U P A 1 C8_1 C 0.2146(4) 0.9595(3) 0.4982(3) 0.0343(7) Uani 0.563(3) 1 d . U P A 1 H8_1 H 0.1535 1.0092 0.5507 0.041 Uiso 0.563(3) 1 calc R U P A 1 C9_1 C 0.3406(4) 0.8689(3) 0.5202(3) 0.0268(6) Uani 0.563(3) 1 d . U P A 1 C10_1 C 0.4798(15) 0.7381(13) 0.2607(10) 0.0257(10) Uani 0.563(3) 1 d . U P A 1 H10_1 H 0.5566 0.6647 0.2824 0.031 Uiso 0.563(3) 1 calc R U P A 1 C11_1 C 0.3839(11) 0.6990(11) 0.2145(7) 0.0335(15) Uani 0.563(3) 1 d . U P A 1 H11A_1 H 0.4344 0.6465 0.1573 0.050 Uiso 0.563(3) 1 calc R U P A 1 H11B_1 H 0.3058 0.7680 0.1923 0.050 Uiso 0.563(3) 1 calc R U P A 1 H11C_1 H 0.3477 0.6563 0.2632 0.050 Uiso 0.563(3) 1 calc R U P A 1 C12_1 C 0.5532(13) 0.8000(10) 0.1847(11) 0.0317(16) Uani 0.563(3) 1 d . U P A 1 H12A_1 H 0.6097 0.7435 0.1313 0.047 Uiso 0.563(3) 1 calc R U P A 1 H12B_1 H 0.6135 0.8258 0.2198 0.047 Uiso 0.563(3) 1 calc R U P A 1 H12C_1 H 0.4814 0.8687 0.1562 0.047 Uiso 0.563(3) 1 calc R U P A 1 C13_1 C 0.3807(4) 0.8561(3) 0.6262(2) 0.0292(6) Uani 0.563(3) 1 d . U P A 1 H13_1 H 0.4586 0.7763 0.6316 0.035 Uiso 0.563(3) 1 calc R U P A 1 C14_1 C 0.2579(4) 0.8649(3) 0.7022(3) 0.0384(8) Uani 0.563(3) 1 d . U P A 1 H14A_1 H 0.2905 0.8482 0.7687 0.058 Uiso 0.563(3) 1 calc R U P A 1 H14B_1 H 0.2217 0.8074 0.6842 0.058 Uiso 0.563(3) 1 calc R U P A 1 H14C_1 H 0.1835 0.9449 0.7022 0.058 Uiso 0.563(3) 1 calc R U P A 1 C15_1 C 0.4338(5) 0.9505(3) 0.6522(3) 0.0458(9) Uani 0.563(3) 1 d . U P A 1 H15A_1 H 0.4665 0.9364 0.7187 0.069 Uiso 0.563(3) 1 calc R U P A 1 H15B_1 H 0.3574 1.0293 0.6509 0.069 Uiso 0.563(3) 1 calc R U P A 1 H15C_1 H 0.5113 0.9456 0.6033 0.069 Uiso 0.563(3) 1 calc R U P A 1 C16_1 C 0.8022(4) 0.4863(3) 0.6040(3) 0.0204(7) Uani 0.563(3) 1 d . U P A 1 C17_1 C 0.8705(5) 0.3666(4) 0.5777(3) 0.0217(8) Uani 0.563(3) 1 d . U P A 1 C18_1 C 0.9435(4) 0.2880(3) 0.6495(3) 0.0261(7) Uani 0.563(3) 1 d . U P A 1 H18_1 H 0.9877 0.2058 0.6334 0.031 Uiso 0.563(3) 1 calc R U P A 1 C19_1 C 0.9531(4) 0.3266(5) 0.7432(3) 0.0247(7) Uani 0.563(3) 1 d . U P A 1 C20_1 C 0.8859(4) 0.4464(4) 0.7653(3) 0.0244(7) Uani 0.563(3) 1 d . U P A 1 H20_1 H 0.8923 0.4741 0.8289 0.029 Uiso 0.563(3) 1 calc R U P A 1 C21_1 C 0.8093(4) 0.5280(4) 0.6984(3) 0.0219(7) Uani 0.563(3) 1 d . U P A 1 C22_1 C 0.7378(4) 0.6576(4) 0.7282(3) 0.0307(9) Uani 0.563(3) 1 d . U P A 1 H22A_1 H 0.7254 0.6658 0.8009 0.046 Uiso 0.563(3) 1 calc R U P A 1 H22B_1 H 0.6461 0.6926 0.7020 0.046 Uiso 0.563(3) 1 calc R U P A 1 H22C_1 H 0.7955 0.6985 0.7010 0.046 Uiso 0.563(3) 1 calc R U P A 1 C23_1 C 0.8695(7) 0.3205(5) 0.4763(5) 0.0293(11) Uani 0.563(3) 1 d . U P A 1 H23A_1 H 0.9458 0.2418 0.4654 0.044 Uiso 0.563(3) 1 calc R U P A 1 H23B_1 H 0.8822 0.3743 0.4261 0.044 Uiso 0.563(3) 1 calc R U P A 1 H23C_1 H 0.7798 0.3154 0.4712 0.044 Uiso 0.563(3) 1 calc R U P A 1 C24_1 C 1.0362(5) 0.2395(4) 0.8173(3) 0.0385(9) Uani 0.563(3) 1 d . U P A 1 H24A_1 H 1.1011 0.2677 0.8435 0.058 Uiso 0.563(3) 1 calc R U P A 1 H24B_1 H 1.0891 0.1621 0.7843 0.058 Uiso 0.563(3) 1 calc R U P A 1 H24C_1 H 0.9721 0.2323 0.8720 0.058 Uiso 0.563(3) 1 calc R U P A 1 N1_11 N 0.5625(6) 0.7110(6) 0.4573(6) 0.0197(9) Uani 0.437(3) 1 d . U P A 2 N2_11 N 0.7593(6) 0.5365(4) 0.5244(5) 0.0213(8) Uani 0.437(3) 1 d . U P A 2 C1_11 C 0.5964(10) 0.6107(10) 0.5111(11) 0.0199(11) Uani 0.437(3) 1 d . U P A 2 C2_11 C 0.6799(5) 0.7474(4) 0.4398(4) 0.0230(9) Uani 0.437(3) 1 d . U P A 2 H2A_11 H 0.6583 0.8233 0.4747 0.028 Uiso 0.437(3) 1 calc R U P A 2 H2AB_11 H 0.7018 0.7556 0.3679 0.028 Uiso 0.437(3) 1 calc R U P A 2 C3_11 C 0.7996(5) 0.6475(4) 0.4822(4) 0.0223(8) Uani 0.437(3) 1 d . U P A 2 H3A_11 H 0.8306 0.6793 0.5374 0.027 Uiso 0.437(3) 1 calc R U P A 2 H3AB_11 H 0.8792 0.6159 0.4300 0.027 Uiso 0.437(3) 1 calc R U P A 2 C4_11 C 0.4250(6) 0.7953(7) 0.4389(6) 0.0222(9) Uani 0.437(3) 1 d . U P A 2 C5_11 C 0.3882(8) 0.8153(9) 0.3410(6) 0.0246(10) Uani 0.437(3) 1 d . U P A 2 C6_11 C 0.2946(6) 0.9197(5) 0.3502(4) 0.0333(10) Uani 0.437(3) 1 d . U P A 2 H6_11 H 0.2639 0.9552 0.2890 0.040 Uiso 0.437(3) 1 calc R U P A 2 C7_11 C 0.2294(5) 0.9913(4) 0.4324(4) 0.0382(8) Uani 0.437(3) 1 d . U P A 2 H7_11 H 0.1485 1.0623 0.4263 0.046 Uiso 0.437(3) 1 calc R U P A 2 C8_11 C 0.2802(5) 0.9607(4) 0.5234(3) 0.0336(8) Uani 0.437(3) 1 d . U P A 2 H8_11 H 0.2318 1.0101 0.5798 0.040 Uiso 0.437(3) 1 calc R U P A 2 C9_11 C 0.4002(5) 0.8599(4) 0.5354(3) 0.0277(8) Uani 0.437(3) 1 d . U P A 2 C10_11 C 0.489(2) 0.7430(17) 0.2562(13) 0.0263(12) Uani 0.437(3) 1 d . U P A 2 H10_11 H 0.5734 0.6796 0.2815 0.032 Uiso 0.437(3) 1 calc R U P A 2 C11_11 C 0.4061(14) 0.6865(14) 0.1942(9) 0.0300(18) Uani 0.437(3) 1 d . U P A 2 H11A_11 H 0.4706 0.6338 0.1413 0.045 Uiso 0.437(3) 1 calc R U P A 2 H11B_11 H 0.3293 0.7501 0.1649 0.045 Uiso 0.437(3) 1 calc R U P A 2 H11C_11 H 0.3682 0.6414 0.2390 0.045 Uiso 0.437(3) 1 calc R U P A 2 C12_11 C 0.5290(16) 0.8189(14) 0.1880(14) 0.0311(19) Uani 0.437(3) 1 d . U P A 2 H12A_11 H 0.5853 0.7723 0.1293 0.047 Uiso 0.437(3) 1 calc R U P A 2 H12B_11 H 0.5839 0.8523 0.2214 0.047 Uiso 0.437(3) 1 calc R U P A 2 H12C_11 H 0.4446 0.8832 0.1674 0.047 Uiso 0.437(3) 1 calc R U P A 2 C13_11 C 0.4577(6) 0.8350(4) 0.6363(3) 0.0348(9) Uani 0.437(3) 1 d . U P A 2 H13_11 H 0.5215 0.7491 0.6369 0.042 Uiso 0.437(3) 1 calc R U P A 2 C14_11 C 0.3442(7) 0.8597(5) 0.7230(4) 0.0615(15) Uani 0.437(3) 1 d . U P A 2 H14A_11 H 0.3880 0.8304 0.7844 0.092 Uiso 0.437(3) 1 calc R U P A 2 H14B_11 H 0.2842 0.8193 0.7101 0.092 Uiso 0.437(3) 1 calc R U P A 2 H14C_11 H 0.2875 0.9450 0.7299 0.092 Uiso 0.437(3) 1 calc R U P A 2 C15_11 C 0.5451(8) 0.9054(5) 0.6499(4) 0.0582(14) Uani 0.437(3) 1 d . U P A 2 H15A_11 H 0.5777 0.8922 0.7164 0.087 Uiso 0.437(3) 1 calc R U P A 2 H15B_11 H 0.4877 0.9898 0.6424 0.087 Uiso 0.437(3) 1 calc R U P A 2 H15C_11 H 0.6259 0.8794 0.5997 0.087 Uiso 0.437(3) 1 calc R U P A 2 C16_11 C 0.8246(6) 0.4452(5) 0.5942(4) 0.0219(9) Uani 0.437(3) 1 d . U P A 2 C17_11 C 0.8793(6) 0.3265(5) 0.5667(5) 0.0242(10) Uani 0.437(3) 1 d . U P A 2 C18_11 C 0.9531(6) 0.2431(5) 0.6337(4) 0.0295(9) Uani 0.437(3) 1 d . U P A 2 H18_11 H 0.9903 0.1616 0.6155 0.035 Uiso 0.437(3) 1 calc R U P A 2 C19_11 C 0.9741(5) 0.2760(5) 0.7271(4) 0.0291(9) Uani 0.437(3) 1 d . U P A 2 C20_11 C 0.9195(5) 0.3938(6) 0.7532(4) 0.0260(9) Uani 0.437(3) 1 d . U P A 2 H20_11 H 0.9331 0.4167 0.8167 0.031 Uiso 0.437(3) 1 calc R U P A 2 C21_11 C 0.8441(5) 0.4813(5) 0.6885(4) 0.0255(9) Uani 0.437(3) 1 d . U P A 2 C22_11 C 0.7850(6) 0.6088(5) 0.7219(4) 0.0301(11) Uani 0.437(3) 1 d . U P A 2 H22A_11 H 0.8425 0.6193 0.7707 0.045 Uiso 0.437(3) 1 calc R U P A 2 H22B_11 H 0.6889 0.6322 0.7523 0.045 Uiso 0.437(3) 1 calc R U P A 2 H22C_11 H 0.7851 0.6583 0.6644 0.045 Uiso 0.437(3) 1 calc R U P A 2 C23_11 C 0.8627(9) 0.2859(6) 0.4672(6) 0.0301(13) Uani 0.437(3) 1 d . U P A 2 H23A_11 H 0.9040 0.1992 0.4637 0.045 Uiso 0.437(3) 1 calc R U P A 2 H23B_11 H 0.9103 0.3159 0.4151 0.045 Uiso 0.437(3) 1 calc R U P A 2 H23C_11 H 0.7630 0.3158 0.4577 0.045 Uiso 0.437(3) 1 calc R U P A 2 C24_11 C 1.0558(7) 0.1843(6) 0.7994(5) 0.0470(14) Uani 0.437(3) 1 d . U P A 2 H24A_11 H 1.0196 0.2135 0.8678 0.070 Uiso 0.437(3) 1 calc R U P A 2 H24B_11 H 1.1550 0.1700 0.7888 0.070 Uiso 0.437(3) 1 calc R U P A 2 H24C_11 H 1.0458 0.1104 0.7885 0.070 Uiso 0.437(3) 1 calc R U P A 2 C1_3 C 0.2905(8) 0.9866(8) -0.0035(5) 0.078(2) Uiso 0.5 1 d . . P B 3 H1_3 H 0.3686 0.9347 -0.0456 0.094 Uiso 0.5 1 calc R U P B 3 C2_3 C 0.1874(8) 0.9546(5) 0.0296(5) 0.0612(15) Uiso 0.5 1 d . . P B 3 H2_3 H 0.1888 0.8808 0.0103 0.073 Uiso 0.5 1 calc R U P B 3 C3_3 C 0.0793(7) 1.0319(7) 0.0924(5) 0.0665(15) Uiso 0.5 1 d . . P B 3 H3_3 H 0.0095 1.0059 0.1182 0.080 Uiso 0.5 1 calc R U P B 3 C4_3 C 0.0621(7) 1.1429(6) 0.1217(4) 0.0652(14) Uiso 0.5 1 d . . P B 3 H4_3 H -0.0156 1.1931 0.1649 0.078 Uiso 0.5 1 calc R U P B 3 C5_3 C 0.1662(9) 1.1748(6) 0.0834(6) 0.0729(18) Uiso 0.5 1 d . . P B 3 H5_3 H 0.1591 1.2520 0.0975 0.087 Uiso 0.5 1 calc R U P B 3 C6_3 C 0.2816(7) 1.0980(8) 0.0248(5) 0.0669(15) Uiso 0.5 1 d . . P B 3 H6_3 H 0.3556 1.1208 0.0034 0.080 Uiso 0.5 1 calc R U P B 3 C1_13 C 0.2427(7) 1.1504(6) 0.0499(4) 0.0509(11) Uiso 0.5 1 d . . P C 4 H1_13 H 0.2768 1.2107 0.0457 0.061 Uiso 0.5 1 calc R U P C 4 C2_13 C 0.2623(7) 0.9604(5) 0.0002(4) 0.0475(13) Uiso 0.5 1 d . . P C 4 H2_13 H 0.3088 0.8906 -0.0399 0.057 Uiso 0.5 1 calc R U P C 4 C3_13 C 0.1456(7) 0.9728(6) 0.0640(5) 0.0563(14) Uiso 0.5 1 d . . P C 4 H3_13 H 0.1154 0.9102 0.0695 0.068 Uiso 0.5 1 calc R U P C 4 C4_13 C 0.0727(7) 1.0765(7) 0.1198(5) 0.0650(15) Uiso 0.5 1 d . . P C 4 H4_13 H -0.0093 1.0872 0.1621 0.078 Uiso 0.5 1 calc R U P C 4 C5_13 C 0.1238(8) 1.1650(6) 0.1119(5) 0.0642(15) Uiso 0.5 1 d . . P C 4 H5_13 H 0.0759 1.2364 0.1499 0.077 Uiso 0.5 1 calc R U P C 4 C6_13 C 0.3112(5) 1.0465(6) -0.0058(4) 0.0475(11) Uiso 0.5 1 d . . P C 4 H6_13 H 0.3930 1.0353 -0.0486 0.057 Uiso 0.5 1 calc R U P C 4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0296(6) 0.0385(6) 0.0193(5) -0.0042(4) 0.0022(4) -0.0244(5) B3 0.0198(8) 0.0204(8) 0.0221(8) -0.0008(6) -0.0019(6) -0.0116(7) O2 0.0220(5) 0.0331(6) 0.0178(5) -0.0032(4) 0.0013(4) -0.0168(5) B4 0.0178(7) 0.0218(8) 0.0198(8) -0.0004(6) -0.0012(6) -0.0122(7) C1 0.0239(8) 0.0309(8) 0.0175(7) -0.0019(6) 0.0001(6) -0.0138(7) C5 0.0266(8) 0.0320(8) 0.0216(7) -0.0021(6) 0.0020(6) -0.0180(7) C2 0.0323(9) 0.0589(12) 0.0263(8) -0.0039(8) 0.0025(7) -0.0311(9) C3 0.0386(10) 0.0551(11) 0.0229(8) -0.0073(8) -0.0006(7) -0.0306(9) C4 0.0435(10) 0.0638(13) 0.0180(8) -0.0070(8) 0.0039(7) -0.0308(10) C6 0.0393(10) 0.0710(14) 0.0240(8) -0.0047(8) 0.0083(7) -0.0353(10) N1_1 0.0219(17) 0.0269(16) 0.0231(11) 0.0017(12) -0.0018(14) -0.0156(13) N2_1 0.0204(15) 0.0273(16) 0.0227(12) 0.0028(13) -0.0028(11) -0.0157(13) C1_1 0.022(2) 0.026(2) 0.0136(13) -0.0019(15) -0.0007(16) -0.0166(16) C2_1 0.0242(17) 0.0417(19) 0.0327(15) 0.0086(16) -0.0041(13) -0.0218(15) C3_1 0.0269(18) 0.040(2) 0.0354(15) 0.0071(15) -0.0021(14) -0.0241(15) C4_1 0.0281(18) 0.0212(12) 0.0279(14) 0.0000(11) 0.0013(13) -0.0159(15) C5_1 0.0263(17) 0.0236(12) 0.0333(17) 0.0028(13) -0.0005(13) -0.0135(14) C6_1 0.0340(17) 0.0237(14) 0.0405(18) 0.0000(13) -0.0079(13) -0.0089(12) C7_1 0.0345(16) 0.0270(14) 0.0457(16) -0.0001(12) -0.0061(13) -0.0045(12) C8_1 0.0333(15) 0.0239(13) 0.0405(15) -0.0054(11) -0.0002(13) -0.0066(12) C9_1 0.0316(14) 0.0221(12) 0.0304(13) -0.0002(10) 0.0005(11) -0.0154(12) C10_1 0.0249(19) 0.0263(16) 0.0292(16) 0.0067(13) -0.0002(14) -0.0146(13) C11_1 0.030(3) 0.036(3) 0.038(3) 0.002(2) -0.006(2) -0.016(2) C12_1 0.029(4) 0.031(3) 0.033(2) 0.009(2) -0.001(2) -0.012(3) C13_1 0.0380(15) 0.0226(13) 0.0288(13) -0.0028(10) 0.0023(13) -0.0152(13) C14_1 0.046(2) 0.0348(18) 0.0298(16) -0.0012(13) 0.0073(15) -0.0136(16) C15_1 0.074(2) 0.0401(19) 0.0367(17) -0.0027(14) -0.0033(17) -0.0376(18) C16_1 0.0154(14) 0.0278(17) 0.0240(13) 0.0006(13) -0.0005(10) -0.0151(13) C17_1 0.0164(13) 0.029(2) 0.0252(14) 0.0003(15) -0.0026(10) -0.0152(16) C18_1 0.0191(12) 0.0310(17) 0.0296(15) 0.0001(14) -0.0002(11) -0.0122(14) C19_1 0.0198(14) 0.0330(19) 0.0243(13) 0.0021(15) -0.0010(11) -0.0141(16) C20_1 0.0207(15) 0.0343(17) 0.0229(13) 0.0017(13) -0.0015(11) -0.0163(13) C21_1 0.0180(15) 0.0293(18) 0.0238(13) -0.0007(14) -0.0009(11) -0.0153(14) C22_1 0.031(2) 0.030(2) 0.0348(18) -0.0055(17) -0.0045(17) -0.0156(16) C23_1 0.0200(17) 0.033(3) 0.035(2) -0.0057(19) -0.0040(13) -0.0095(19) C24_1 0.034(2) 0.048(2) 0.0328(19) 0.0107(19) -0.0047(15) -0.016(2) N1_11 0.0215(19) 0.0247(18) 0.0216(13) 0.0016(14) -0.0017(16) -0.0183(15) N2_11 0.0170(17) 0.0300(19) 0.0231(14) 0.0030(16) -0.0021(12) -0.0160(15) C1_11 0.018(2) 0.028(2) 0.0180(16) -0.0030(17) -0.0052(17) -0.0126(17) C2_11 0.0178(19) 0.0248(19) 0.0305(17) 0.0028(15) 0.0001(15) -0.0134(15) C3_11 0.0176(18) 0.0253(19) 0.0295(16) 0.0040(16) 0.0004(14) -0.0149(15) C4_11 0.0227(18) 0.0207(14) 0.0296(15) 0.0004(12) -0.0050(14) -0.0149(15) C5_11 0.0275(19) 0.0222(13) 0.0306(17) 0.0013(13) -0.0078(13) -0.0159(14) C6_11 0.0320(19) 0.0263(16) 0.043(2) 0.0042(15) -0.0091(15) -0.0118(14) C7_11 0.0344(17) 0.0263(15) 0.0493(18) -0.0013(14) -0.0032(15) -0.0079(14) C8_11 0.0335(17) 0.0240(15) 0.0426(17) -0.0046(13) 0.0026(14) -0.0123(14) C9_11 0.0323(16) 0.0214(13) 0.0343(15) -0.0025(11) 0.0005(14) -0.0166(14) C10_11 0.025(2) 0.028(2) 0.030(2) -0.0017(17) -0.0075(18) -0.0136(16) C11_11 0.026(4) 0.030(3) 0.033(4) -0.002(3) -0.010(3) -0.010(3) C12_11 0.026(4) 0.036(4) 0.030(3) -0.002(3) -0.001(3) -0.012(3) C13_11 0.051(2) 0.0272(18) 0.0283(16) -0.0051(14) 0.0004(17) -0.0185(18) C14_11 0.076(3) 0.041(2) 0.043(2) -0.002(2) 0.014(2) -0.002(3) C15_11 0.095(4) 0.045(3) 0.055(3) 0.006(2) -0.029(3) -0.046(3) C16_11 0.0180(16) 0.031(2) 0.0219(15) 0.0039(17) -0.0036(13) -0.0147(16) C17_11 0.0146(14) 0.031(2) 0.0311(17) 0.0010(17) 0.0000(12) -0.0139(17) C18_11 0.0195(15) 0.036(2) 0.0328(17) 0.0045(17) -0.0036(13) -0.0115(18) C19_11 0.0206(16) 0.038(2) 0.0305(17) 0.0062(17) -0.0012(13) -0.0142(17) C20_11 0.0200(18) 0.036(2) 0.0245(16) 0.0027(19) -0.0043(13) -0.0141(18) C21_11 0.0195(17) 0.034(2) 0.0273(15) 0.0007(16) -0.0013(13) -0.0154(15) C22_11 0.027(3) 0.037(3) 0.031(2) -0.001(2) -0.0062(19) -0.016(2) C23_11 0.021(2) 0.035(3) 0.033(2) -0.002(2) -0.0039(17) -0.009(3) C24_11 0.038(3) 0.054(3) 0.039(3) 0.015(3) -0.007(2) -0.010(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C5 O1 B3 107.11(11) . . O2 B3 O1 107.09(12) . . O2 B3 B4 123.95(12) . . O1 B3 B4 128.96(12) . . C1 O2 B3 107.16(11) . . C1_11 B4 B4 115.1(5) . 2_666 C1_1 B4 B4 113.9(4) . 2_666 C1_11 B4 B3 120.0(5) . . C1_1 B4 B3 120.9(4) . . B4 B4 B3 124.82(15) 2_666 . O2 C1 C2 128.52(14) . . O2 C1 C5 109.43(12) . . C2 C1 C5 122.00(14) . . O1 C5 C3 129.02(14) . . O1 C5 C1 109.18(13) . . C3 C5 C1 121.76(14) . . C1 C2 C6 116.72(15) . . C1 C2 H009 121.6 . . C6 C2 H009 121.6 . . C5 C3 C4 116.86(15) . . C5 C3 H00A 121.6 . . C4 C3 H00A 121.6 . . C6 C4 C3 121.20(15) . . C6 C4 H00B 119.4 . . C3 C4 H00B 119.4 . . C4 C6 C2 121.46(15) . . C4 C6 H00I 119.3 . . C2 C6 H00I 119.3 . . C1_1 N1_1 C4_1 127.0(5) . . C1_1 N1_1 C3_1 111.7(4) . . C4_1 N1_1 C3_1 119.2(5) . . C1_1 N2_1 C16_1 123.2(7) . . C1_1 N2_1 C2_1 125.2(7) . . C16_1 N2_1 C2_1 109.0(4) . . N2_1 C1_1 N1_1 100.8(8) . . N2_1 C1_1 B4 134.6(8) . . N1_1 C1_1 B4 124.4(5) . . N2_1 C2_1 C3_1 91.6(3) . . N2_1 C2_1 H2A_1 113.4 . . C3_1 C2_1 H2A_1 113.4 . . N2_1 C2_1 H2AB_1 113.4 . . C3_1 C2_1 H2AB_1 113.4 . . H2A_1 C2_1 H2AB_1 110.7 . . N1_1 C3_1 C2_1 103.4(3) . . N1_1 C3_1 H3A_1 111.1 . . C2_1 C3_1 H3A_1 111.1 . . N1_1 C3_1 H3AB_1 111.1 . . C2_1 C3_1 H3AB_1 111.1 . . H3A_1 C3_1 H3AB_1 109.0 . . C5_1 C4_1 N1_1 118.8(5) . . C5_1 C4_1 C9_1 104.8(4) . . N1_1 C4_1 C9_1 135.9(5) . . C4_1 C5_1 C10_1 124.9(8) . . C4_1 C5_1 C6_1 129.6(5) . . C10_1 C5_1 C6_1 104.0(7) . . C7_1 C6_1 C5_1 114.7(4) . . C7_1 C6_1 H6_1 122.7 . . C5_1 C6_1 H6_1 122.7 . . C8_1 C7_1 C6_1 119.8(3) . . C8_1 C7_1 H7_1 120.1 . . C6_1 C7_1 H7_1 120.1 . . C7_1 C8_1 C9_1 122.1(3) . . C7_1 C8_1 H8_1 119.0 . . C9_1 C8_1 H8_1 119.0 . . C8_1 C9_1 C4_1 128.3(4) . . C8_1 C9_1 C13_1 119.6(3) . . C4_1 C9_1 C13_1 111.2(3) . . C11_1 C10_1 C5_1 113.4(9) . . C11_1 C10_1 C12_1 113.2(12) . . C5_1 C10_1 C12_1 111.1(11) . . C11_1 C10_1 H10_1 106.2 . . C5_1 C10_1 H10_1 106.2 . . C12_1 C10_1 H10_1 106.2 . . C10_1 C11_1 H11A_1 109.5 . . C10_1 C11_1 H11B_1 109.5 . . H11A_1 C11_1 H11B_1 109.5 . . C10_1 C11_1 H11C_1 109.5 . . H11A_1 C11_1 H11C_1 109.5 . . H11B_1 C11_1 H11C_1 109.5 . . C10_1 C12_1 H12A_1 109.5 . . C10_1 C12_1 H12B_1 109.5 . . H12A_1 C12_1 H12B_1 109.5 . . C10_1 C12_1 H12C_1 109.5 . . H12A_1 C12_1 H12C_1 109.5 . . H12B_1 C12_1 H12C_1 109.5 . . C9_1 C13_1 C14_1 112.0(3) . . C9_1 C13_1 C15_1 110.9(3) . . C14_1 C13_1 C15_1 109.4(3) . . C9_1 C13_1 H13_1 108.1 . . C14_1 C13_1 H13_1 108.1 . . C15_1 C13_1 H13_1 108.1 . . C13_1 C14_1 H14A_1 109.5 . . C13_1 C14_1 H14B_1 109.5 . . H14A_1 C14_1 H14B_1 109.5 . . C13_1 C14_1 H14C_1 109.5 . . H14A_1 C14_1 H14C_1 109.5 . . H14B_1 C14_1 H14C_1 109.5 . . C13_1 C15_1 H15A_1 109.5 . . C13_1 C15_1 H15B_1 109.5 . . H15A_1 C15_1 H15B_1 109.5 . . C13_1 C15_1 H15C_1 109.5 . . H15A_1 C15_1 H15C_1 109.5 . . H15B_1 C15_1 H15C_1 109.5 . . C17_1 C16_1 C21_1 121.1(4) . . C17_1 C16_1 N2_1 121.3(3) . . C21_1 C16_1 N2_1 117.3(3) . . C16_1 C17_1 C18_1 118.0(4) . . C16_1 C17_1 C23_1 122.2(4) . . C18_1 C17_1 C23_1 119.8(4) . . C19_1 C18_1 C17_1 122.1(4) . . C19_1 C18_1 H18_1 118.9 . . C17_1 C18_1 H18_1 118.9 . . C20_1 C19_1 C18_1 117.8(4) . . C20_1 C19_1 C24_1 121.7(4) . . C18_1 C19_1 C24_1 120.5(4) . . C19_1 C20_1 C21_1 122.7(3) . . C19_1 C20_1 H20_1 118.6 . . C21_1 C20_1 H20_1 118.6 . . C20_1 C21_1 C16_1 118.2(4) . . C20_1 C21_1 C22_1 119.7(3) . . C16_1 C21_1 C22_1 122.1(3) . . C21_1 C22_1 H22A_1 109.5 . . C21_1 C22_1 H22B_1 109.5 . . H22A_1 C22_1 H22B_1 109.5 . . C21_1 C22_1 H22C_1 109.5 . . H22A_1 C22_1 H22C_1 109.5 . . H22B_1 C22_1 H22C_1 109.5 . . C17_1 C23_1 H23A_1 109.5 . . C17_1 C23_1 H23B_1 109.5 . . H23A_1 C23_1 H23B_1 109.5 . . C17_1 C23_1 H23C_1 109.5 . . H23A_1 C23_1 H23C_1 109.5 . . H23B_1 C23_1 H23C_1 109.5 . . C19_1 C24_1 H24A_1 109.5 . . C19_1 C24_1 H24B_1 109.5 . . H24A_1 C24_1 H24B_1 109.5 . . C19_1 C24_1 H24C_1 109.5 . . H24A_1 C24_1 H24C_1 109.5 . . H24B_1 C24_1 H24C_1 109.5 . . C1_11 N1_11 C4_11 127.6(7) . . C1_11 N1_11 C2_11 112.3(6) . . C4_11 N1_11 C2_11 118.1(6) . . C16_11 N2_11 C1_11 129.7(7) . . C16_11 N2_11 C3_11 130.7(5) . . C1_11 N2_11 C3_11 91.9(6) . . N1_11 C1_11 B4 129.5(7) . . N1_11 C1_11 N2_11 116.9(9) . . B4 C1_11 N2_11 112.2(8) . . N1_11 C2_11 C3_11 103.4(4) . . N1_11 C2_11 H2A_11 111.1 . . C3_11 C2_11 H2A_11 111.1 . . N1_11 C2_11 H2AB_11 111.1 . . C3_11 C2_11 H2AB_11 111.1 . . H2A_11 C2_11 H2AB_11 109.0 . . C2_11 C3_11 N2_11 113.8(4) . . C2_11 C3_11 H3A_11 108.8 . . N2_11 C3_11 H3A_11 108.8 . . C2_11 C3_11 H3AB_11 108.8 . . N2_11 C3_11 H3AB_11 108.8 . . H3A_11 C3_11 H3AB_11 107.7 . . C5_11 C4_11 N1_11 119.7(6) . . C5_11 C4_11 C9_11 140.4(7) . . N1_11 C4_11 C9_11 94.1(5) . . C6_11 C5_11 C4_11 100.4(7) . . C6_11 C5_11 C10_11 134.4(10) . . C4_11 C5_11 C10_11 120.0(10) . . C5_11 C6_11 C7_11 131.8(7) . . C5_11 C6_11 H6_11 114.1 . . C7_11 C6_11 H6_11 114.1 . . C6_11 C7_11 C8_11 120.3(4) . . C6_11 C7_11 H7_11 119.8 . . C8_11 C7_11 H7_11 119.8 . . C7_11 C8_11 C9_11 121.9(4) . . C7_11 C8_11 H8_11 119.1 . . C9_11 C8_11 H8_11 119.1 . . C8_11 C9_11 C4_11 102.5(4) . . C8_11 C9_11 C13_11 119.7(4) . . C4_11 C9_11 C13_11 137.2(5) . . C12_11 C10_11 C5_11 110.5(15) . . C12_11 C10_11 C11_11 106.5(15) . . C5_11 C10_11 C11_11 107.1(11) . . C12_11 C10_11 H10_11 110.9 . . C5_11 C10_11 H10_11 110.9 . . C11_11 C10_11 H10_11 110.9 . . C10_11 C11_11 H11A_11 109.5 . . C10_11 C11_11 H11B_11 109.5 . . H11A_11 C11_11 H11B_11 109.5 . . C10_11 C11_11 H11C_11 109.5 . . H11A_11 C11_11 H11C_11 109.5 . . H11B_11 C11_11 H11C_11 109.5 . . C10_11 C12_11 H12A_11 109.5 . . C10_11 C12_11 H12B_11 109.5 . . H12A_11 C12_11 H12B_11 109.5 . . C10_11 C12_11 H12C_11 109.5 . . H12A_11 C12_11 H12C_11 109.5 . . H12B_11 C12_11 H12C_11 109.5 . . C9_11 C13_11 C15_11 109.9(4) . . C9_11 C13_11 C14_11 113.3(5) . . C15_11 C13_11 C14_11 110.7(5) . . C9_11 C13_11 H13_11 107.6 . . C15_11 C13_11 H13_11 107.6 . . C14_11 C13_11 H13_11 107.6 . . C13_11 C14_11 H14A_11 109.5 . . C13_11 C14_11 H14B_11 109.5 . . H14A_11 C14_11 H14B_11 109.5 . . C13_11 C14_11 H14C_11 109.5 . . H14A_11 C14_11 H14C_11 109.5 . . H14B_11 C14_11 H14C_11 109.5 . . C13_11 C15_11 H15A_11 109.5 . . C13_11 C15_11 H15B_11 109.5 . . H15A_11 C15_11 H15B_11 109.5 . . C13_11 C15_11 H15C_11 109.5 . . H15A_11 C15_11 H15C_11 109.5 . . H15B_11 C15_11 H15C_11 109.5 . . C17_11 C16_11 C21_11 120.8(5) . . C17_11 C16_11 N2_11 121.3(5) . . C21_11 C16_11 N2_11 117.6(5) . . C16_11 C17_11 C18_11 118.7(5) . . C16_11 C17_11 C23_11 122.0(5) . . C18_11 C17_11 C23_11 119.3(5) . . C17_11 C18_11 C19_11 121.8(5) . . C17_11 C18_11 H18_11 119.1 . . C19_11 C18_11 H18_11 119.1 . . C20_11 C19_11 C18_11 118.8(5) . . C20_11 C19_11 C24_11 119.7(5) . . C18_11 C19_11 C24_11 121.5(5) . . C19_11 C20_11 C21_11 121.6(5) . . C19_11 C20_11 H20_11 119.2 . . C21_11 C20_11 H20_11 119.2 . . C20_11 C21_11 C16_11 118.3(5) . . C20_11 C21_11 C22_11 119.1(5) . . C16_11 C21_11 C22_11 122.5(5) . . C21_11 C22_11 H22A_11 109.5 . . C21_11 C22_11 H22B_11 109.5 . . H22A_11 C22_11 H22B_11 109.5 . . C21_11 C22_11 H22C_11 109.5 . . H22A_11 C22_11 H22C_11 109.5 . . H22B_11 C22_11 H22C_11 109.5 . . C17_11 C23_11 H23A_11 109.5 . . C17_11 C23_11 H23B_11 109.5 . . H23A_11 C23_11 H23B_11 109.5 . . C17_11 C23_11 H23C_11 109.5 . . H23A_11 C23_11 H23C_11 109.5 . . H23B_11 C23_11 H23C_11 109.5 . . C19_11 C24_11 H24A_11 109.5 . . C19_11 C24_11 H24B_11 109.5 . . H24A_11 C24_11 H24B_11 109.5 . . C19_11 C24_11 H24C_11 109.5 . . H24A_11 C24_11 H24C_11 109.5 . . H24B_11 C24_11 H24C_11 109.5 . . C2_3 C1_3 C6_3 118.9(7) . . C2_3 C1_3 H1_3 120.6 . . C6_3 C1_3 H1_3 120.6 . . C1_3 C2_3 C3_3 117.9(6) . . C1_3 C2_3 H2_3 121.0 . . C3_3 C2_3 H2_3 121.0 . . C4_3 C3_3 C2_3 126.4(6) . . C4_3 C3_3 H3_3 116.8 . . C2_3 C3_3 H3_3 116.8 . . C5_3 C4_3 C3_3 114.2(6) . . C5_3 C4_3 H4_3 122.9 . . C3_3 C4_3 H4_3 122.9 . . C4_3 C5_3 C6_3 121.8(6) . . C4_3 C5_3 H5_3 119.1 . . C6_3 C5_3 H5_3 119.1 . . C5_3 C6_3 C1_3 120.6(6) . . C5_3 C6_3 H6_3 119.7 . . C1_3 C6_3 H6_3 119.7 . . C6_13 C1_13 C5_13 118.9(5) . . C6_13 C1_13 H1_13 120.5 . . C5_13 C1_13 H1_13 120.5 . . C6_13 C2_13 C3_13 121.1(5) . . C6_13 C2_13 H2_13 119.5 . . C3_13 C2_13 H2_13 119.5 . . C2_13 C3_13 C4_13 120.2(5) . . C2_13 C3_13 H3_13 119.9 . . C4_13 C3_13 H3_13 119.9 . . C3_13 C4_13 C5_13 118.0(6) . . C3_13 C4_13 H4_13 121.0 . . C5_13 C4_13 H4_13 121.0 . . C1_13 C5_13 C4_13 121.4(6) . . C1_13 C5_13 H5_13 119.3 . . C4_13 C5_13 H5_13 119.3 . . C2_13 C6_13 C1_13 120.4(4) . . C2_13 C6_13 H6_13 119.8 . . C1_13 C6_13 H6_13 119.8 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C5 1.3739(17) . O1 B3 1.4250(19) . B3 O2 1.4247(18) . B3 B4 1.652(2) . O2 C1 1.3699(17) . B4 C1_11 1.550(14) . B4 C1_1 1.596(10) . B4 B4 1.608(3) 2_666 C1 C2 1.372(2) . C1 C5 1.385(2) . C5 C3 1.376(2) . C2 C6 1.395(2) . C2 H009 0.9500 . C3 C4 1.394(2) . C3 H00A 0.9500 . C4 C6 1.386(3) . C4 H00B 0.9500 . C6 H00I 0.9500 . N1_1 C1_1 1.344(9) . N1_1 C4_1 1.454(5) . N1_1 C3_1 1.478(6) . N2_1 C1_1 1.173(11) . N2_1 C16_1 1.437(5) . N2_1 C2_1 1.461(7) . C2_1 C3_1 1.529(5) . C2_1 H2A_1 0.9900 . C2_1 H2AB_1 0.9900 . C3_1 H3A_1 0.9900 . C3_1 H3AB_1 0.9900 . C4_1 C5_1 1.392(7) . C4_1 C9_1 1.509(7) . C5_1 C10_1 1.541(16) . C5_1 C6_1 1.594(8) . C6_1 C7_1 1.384(5) . C6_1 H6_1 0.9500 . C7_1 C8_1 1.374(5) . C7_1 H7_1 0.9500 . C8_1 C9_1 1.397(5) . C8_1 H8_1 0.9500 . C9_1 C13_1 1.520(5) . C10_1 C11_1 1.475(18) . C10_1 C12_1 1.594(17) . C10_1 H10_1 1.0000 . C11_1 H11A_1 0.9800 . C11_1 H11B_1 0.9800 . C11_1 H11C_1 0.9800 . C12_1 H12A_1 0.9800 . C12_1 H12B_1 0.9800 . C12_1 H12C_1 0.9800 . C13_1 C14_1 1.539(4) . C13_1 C15_1 1.545(4) . C13_1 H13_1 1.0000 . C14_1 H14A_1 0.9800 . C14_1 H14B_1 0.9800 . C14_1 H14C_1 0.9800 . C15_1 H15A_1 0.9800 . C15_1 H15B_1 0.9800 . C15_1 H15C_1 0.9800 . C16_1 C17_1 1.393(5) . C16_1 C21_1 1.404(5) . C17_1 C18_1 1.405(6) . C17_1 C23_1 1.496(6) . C18_1 C19_1 1.388(5) . C18_1 H18_1 0.9500 . C19_1 C20_1 1.383(5) . C19_1 C24_1 1.513(6) . C20_1 C21_1 1.388(5) . C20_1 H20_1 0.9500 . C21_1 C22_1 1.512(5) . C22_1 H22A_1 0.9800 . C22_1 H22B_1 0.9800 . C22_1 H22C_1 0.9800 . C23_1 H23A_1 0.9800 . C23_1 H23B_1 0.9800 . C23_1 H23C_1 0.9800 . C24_1 H24A_1 0.9800 . C24_1 H24B_1 0.9800 . C24_1 H24C_1 0.9800 . N1_11 C1_11 1.362(12) . N1_11 C4_11 1.438(7) . N1_11 C2_11 1.476(8) . N2_11 C16_11 1.446(7) . N2_11 C1_11 1.605(12) . N2_11 C3_11 1.672(8) . C2_11 C3_11 1.512(6) . C2_11 H2A_11 0.9900 . C2_11 H2AB_11 0.9900 . C3_11 H3A_11 0.9900 . C3_11 H3AB_11 0.9900 . C4_11 C5_11 1.404(9) . C4_11 C9_11 1.487(9) . C5_11 C6_11 1.264(11) . C5_11 C10_11 1.51(2) . C6_11 C7_11 1.372(7) . C6_11 H6_11 0.9500 . C7_11 C8_11 1.373(7) . C7_11 H7_11 0.9500 . C8_11 C9_11 1.387(6) . C8_11 H8_11 0.9500 . C9_11 C13_11 1.520(6) . C10_11 C12_11 1.46(2) . C10_11 C11_11 1.62(2) . C10_11 H10_11 1.0000 . C11_11 H11A_11 0.9800 . C11_11 H11B_11 0.9800 . C11_11 H11C_11 0.9800 . C12_11 H12A_11 0.9800 . C12_11 H12B_11 0.9800 . C12_11 H12C_11 0.9800 . C13_11 C15_11 1.527(7) . C13_11 C14_11 1.529(7) . C13_11 H13_11 1.0000 . C14_11 H14A_11 0.9800 . C14_11 H14B_11 0.9800 . C14_11 H14C_11 0.9800 . C15_11 H15A_11 0.9800 . C15_11 H15B_11 0.9800 . C15_11 H15C_11 0.9800 . C16_11 C17_11 1.386(6) . C16_11 C21_11 1.418(7) . C17_11 C18_11 1.391(7) . C17_11 C23_11 1.494(8) . C18_11 C19_11 1.397(7) . C18_11 H18_11 0.9500 . C19_11 C20_11 1.372(7) . C19_11 C24_11 1.519(7) . C20_11 C21_11 1.401(7) . C20_11 H20_11 0.9500 . C21_11 C22_11 1.502(7) . C22_11 H22A_11 0.9800 . C22_11 H22B_11 0.9800 . C22_11 H22C_11 0.9800 . C23_11 H23A_11 0.9800 . C23_11 H23B_11 0.9800 . C23_11 H23C_11 0.9800 . C24_11 H24A_11 0.9800 . C24_11 H24B_11 0.9800 . C24_11 H24C_11 0.9800 . C1_3 C2_3 1.336(10) . C1_3 C6_3 1.403(11) . C1_3 H1_3 0.9500 . C2_3 C3_3 1.373(9) . C2_3 H2_3 0.9500 . C3_3 C4_3 1.372(9) . C3_3 H3_3 0.9500 . C4_3 C5_3 1.364(10) . C4_3 H4_3 0.9500 . C5_3 C6_3 1.380(10) . C5_3 H5_3 0.9500 . C6_3 H6_3 0.9500 . C1_13 C6_13 1.384(8) . C1_13 C5_13 1.385(8) . C1_13 H1_13 0.9500 . C2_13 C6_13 1.359(8) . C2_13 C3_13 1.385(8) . C2_13 H2_13 0.9500 . C3_13 C4_13 1.388(10) . C3_13 H3_13 0.9500 . C4_13 C5_13 1.403(9) . C4_13 H4_13 0.9500 . C5_13 H5_13 0.9500 . C6_13 H6_13 0.9500 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_4 C5 O1 B3 O2 1.49(16) . . C5 O1 B3 B4 -178.54(15) . . O1 B3 O2 C1 -1.77(16) . . B4 B3 O2 C1 178.25(14) . . O2 B3 B4 C1_11 158.1(4) . . O1 B3 B4 C1_11 -21.8(5) . . O2 B3 B4 C1_1 168.3(3) . . O1 B3 B4 C1_1 -11.7(4) . . O2 B3 B4 B4 -19.4(3) . 2_666 O1 B3 B4 B4 160.63(18) . 2_666 B3 O2 C1 C2 -176.20(17) . . B3 O2 C1 C5 1.40(17) . . B3 O1 C5 C3 176.96(18) . . B3 O1 C5 C1 -0.65(17) . . O2 C1 C5 O1 -0.47(18) . . C2 C1 C5 O1 177.31(15) . . O2 C1 C5 C3 -178.29(16) . . C2 C1 C5 C3 -0.5(3) . . O2 C1 C2 C6 177.62(17) . . C5 C1 C2 C6 0.3(3) . . O1 C5 C3 C4 -177.01(17) . . C1 C5 C3 C4 0.3(3) . . C5 C3 C4 C6 0.0(3) . . C3 C4 C6 C2 -0.2(3) . . C1 C2 C6 C4 0.1(3) . . C16_1 N2_1 C1_1 N1_1 170.7(4) . . C2_1 N2_1 C1_1 N1_1 -29.5(9) . . C16_1 N2_1 C1_1 B4 -5.9(15) . . C2_1 N2_1 C1_1 B4 154.0(8) . . C4_1 N1_1 C1_1 N2_1 -149.2(7) . . C3_1 N1_1 C1_1 N2_1 14.0(8) . . C4_1 N1_1 C1_1 B4 27.8(11) . . C3_1 N1_1 C1_1 B4 -169.0(7) . . B4 B4 C1_1 N2_1 -103.9(12) 2_666 . B3 B4 C1_1 N2_1 69.2(12) . . B4 B4 C1_1 N1_1 80.2(8) 2_666 . B3 B4 C1_1 N1_1 -106.7(7) . . C1_1 N2_1 C2_1 C3_1 29.3(8) . . C16_1 N2_1 C2_1 C3_1 -168.4(3) . . C1_1 N1_1 C3_1 C2_1 1.7(6) . . C4_1 N1_1 C3_1 C2_1 166.4(5) . . N2_1 C2_1 C3_1 N1_1 -13.2(4) . . C1_1 N1_1 C4_1 C5_1 -121.1(8) . . C3_1 N1_1 C4_1 C5_1 76.7(7) . . C1_1 N1_1 C4_1 C9_1 48.6(10) . . C3_1 N1_1 C4_1 C9_1 -113.5(7) . . N1_1 C4_1 C5_1 C10_1 8.5(11) . . C9_1 C4_1 C5_1 C10_1 -164.1(8) . . N1_1 C4_1 C5_1 C6_1 172.7(7) . . C9_1 C4_1 C5_1 C6_1 0.1(9) . . C4_1 C5_1 C6_1 C7_1 6.2(10) . . C10_1 C5_1 C6_1 C7_1 172.9(6) . . C5_1 C6_1 C7_1 C8_1 -5.8(6) . . C6_1 C7_1 C8_1 C9_1 -0.2(6) . . C7_1 C8_1 C9_1 C4_1 8.1(6) . . C7_1 C8_1 C9_1 C13_1 176.6(3) . . C5_1 C4_1 C9_1 C8_1 -7.3(7) . . N1_1 C4_1 C9_1 C8_1 -178.0(5) . . C5_1 C4_1 C9_1 C13_1 -176.6(4) . . N1_1 C4_1 C9_1 C13_1 12.7(8) . . C4_1 C5_1 C10_1 C11_1 121.6(11) . . C6_1 C5_1 C10_1 C11_1 -45.9(11) . . C4_1 C5_1 C10_1 C12_1 -109.6(11) . . C6_1 C5_1 C10_1 C12_1 82.9(12) . . C8_1 C9_1 C13_1 C14_1 46.2(4) . . C4_1 C9_1 C13_1 C14_1 -143.5(4) . . C8_1 C9_1 C13_1 C15_1 -76.4(4) . . C4_1 C9_1 C13_1 C15_1 93.9(4) . . C1_1 N2_1 C16_1 C17_1 83.6(8) . . C2_1 N2_1 C16_1 C17_1 -79.1(5) . . C1_1 N2_1 C16_1 C21_1 -102.4(8) . . C2_1 N2_1 C16_1 C21_1 94.9(4) . . C21_1 C16_1 C17_1 C18_1 2.0(6) . . N2_1 C16_1 C17_1 C18_1 175.7(4) . . C21_1 C16_1 C17_1 C23_1 -177.4(4) . . N2_1 C16_1 C17_1 C23_1 -3.6(6) . . C16_1 C17_1 C18_1 C19_1 -2.3(6) . . C23_1 C17_1 C18_1 C19_1 177.1(4) . . C17_1 C18_1 C19_1 C20_1 1.0(5) . . C17_1 C18_1 C19_1 C24_1 -178.2(4) . . C18_1 C19_1 C20_1 C21_1 0.6(5) . . C24_1 C19_1 C20_1 C21_1 179.8(3) . . C19_1 C20_1 C21_1 C16_1 -0.9(5) . . C19_1 C20_1 C21_1 C22_1 179.6(3) . . C17_1 C16_1 C21_1 C20_1 -0.4(5) . . N2_1 C16_1 C21_1 C20_1 -174.5(3) . . C17_1 C16_1 C21_1 C22_1 179.1(4) . . N2_1 C16_1 C21_1 C22_1 5.1(5) . . C4_11 N1_11 C1_11 B4 18.4(16) . . C2_11 N1_11 C1_11 B4 -177.9(10) . . C4_11 N1_11 C1_11 N2_11 -176.6(9) . . C2_11 N1_11 C1_11 N2_11 -12.9(12) . . B4 B4 C1_11 N1_11 76.6(11) 2_666 . B3 B4 C1_11 N1_11 -101.2(11) . . B4 B4 C1_11 N2_11 -89.0(9) 2_666 . B3 B4 C1_11 N2_11 93.3(8) . . C16_11 N2_11 C1_11 N1_11 163.8(7) . . C3_11 N2_11 C1_11 N1_11 12.6(10) . . C16_11 N2_11 C1_11 B4 -28.7(14) . . C3_11 N2_11 C1_11 B4 -179.9(8) . . C1_11 N1_11 C2_11 C3_11 5.5(8) . . C4_11 N1_11 C2_11 C3_11 170.9(6) . . N1_11 C2_11 C3_11 N2_11 3.1(6) . . C16_11 N2_11 C3_11 C2_11 -159.4(5) . . C1_11 N2_11 C3_11 C2_11 -8.7(7) . . C1_11 N1_11 C4_11 C5_11 -118.9(10) . . C2_11 N1_11 C4_11 C5_11 78.1(9) . . C1_11 N1_11 C4_11 C9_11 82.7(10) . . C2_11 N1_11 C4_11 C9_11 -80.2(7) . . N1_11 C4_11 C5_11 C6_11 -154.1(8) . . C9_11 C4_11 C5_11 C6_11 -9.3(12) . . N1_11 C4_11 C5_11 C10_11 4.1(14) . . C9_11 C4_11 C5_11 C10_11 148.9(11) . . C4_11 C5_11 C6_11 C7_11 -8.3(11) . . C10_11 C5_11 C6_11 C7_11 -161.5(11) . . C5_11 C6_11 C7_11 C8_11 11.9(11) . . C6_11 C7_11 C8_11 C9_11 2.0(7) . . C7_11 C8_11 C9_11 C4_11 -12.1(6) . . C7_11 C8_11 C9_11 C13_11 175.6(4) . . C5_11 C4_11 C9_11 C8_11 19.0(10) . . N1_11 C4_11 C9_11 C8_11 168.9(5) . . C5_11 C4_11 C9_11 C13_11 -170.8(8) . . N1_11 C4_11 C9_11 C13_11 -20.9(9) . . C6_11 C5_11 C10_11 C12_11 31(2) . . C4_11 C5_11 C10_11 C12_11 -118.0(14) . . C6_11 C5_11 C10_11 C11_11 -84.3(16) . . C4_11 C5_11 C10_11 C11_11 126.4(12) . . C8_11 C9_11 C13_11 C15_11 -82.0(6) . . C4_11 C9_11 C13_11 C15_11 109.1(7) . . C8_11 C9_11 C13_11 C14_11 42.4(6) . . C4_11 C9_11 C13_11 C14_11 -126.5(7) . . C1_11 N2_11 C16_11 C17_11 99.4(10) . . C3_11 N2_11 C16_11 C17_11 -120.1(6) . . C1_11 N2_11 C16_11 C21_11 -87.2(10) . . C3_11 N2_11 C16_11 C21_11 53.3(7) . . C21_11 C16_11 C17_11 C18_11 0.4(8) . . N2_11 C16_11 C17_11 C18_11 173.7(5) . . C21_11 C16_11 C17_11 C23_11 -178.9(6) . . N2_11 C16_11 C17_11 C23_11 -5.6(8) . . C16_11 C17_11 C18_11 C19_11 -0.4(8) . . C23_11 C17_11 C18_11 C19_11 178.9(6) . . C17_11 C18_11 C19_11 C20_11 0.3(7) . . C17_11 C18_11 C19_11 C24_11 -179.5(5) . . C18_11 C19_11 C20_11 C21_11 -0.2(7) . . C24_11 C19_11 C20_11 C21_11 179.6(5) . . C19_11 C20_11 C21_11 C16_11 0.2(7) . . C19_11 C20_11 C21_11 C22_11 179.1(4) . . C17_11 C16_11 C21_11 C20_11 -0.3(7) . . N2_11 C16_11 C21_11 C20_11 -173.8(5) . . C17_11 C16_11 C21_11 C22_11 -179.2(5) . . N2_11 C16_11 C21_11 C22_11 7.3(7) . . C6_3 C1_3 C2_3 C3_3 -1.9(9) . . C1_3 C2_3 C3_3 C4_3 3.4(9) . . C2_3 C3_3 C4_3 C5_3 -0.7(9) . . C3_3 C4_3 C5_3 C6_3 -3.3(9) . . C4_3 C5_3 C6_3 C1_3 4.7(9) . . C2_3 C1_3 C6_3 C5_3 -1.9(9) . . C6_13 C2_13 C3_13 C4_13 2.9(8) . . C2_13 C3_13 C4_13 C5_13 -2.2(8) . . C6_13 C1_13 C5_13 C4_13 0.6(8) . . C3_13 C4_13 C5_13 C1_13 0.5(8) . . C3_13 C2_13 C6_13 C1_13 -1.8(7) . . C5_13 C1_13 C6_13 C2_13 0.1(7) . .