#------------------------------------------------------------------------------ #$Date: 2021-11-06 01:12:47 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270329 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565129.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_1565129 loop_ _publ_author_name 'He, Weiying' 'Beattie, D. Dawson' 'Zhou, Hao' 'Bowes, Eric G.' 'Schafer, Laurel L.' 'Love, Jennifer' 'Kennepohl, Pierre' _publ_section_title ; Direct metal-carbon bonding in symmetric bis(C-H) agostic Nickel(I) complexes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC03578A _journal_year 2021 _chemical_absolute_configuration unk _chemical_formula_moiety 'C23 H27 N O' _chemical_formula_sum 'C23 H27 N O' _chemical_formula_weight 333.45 _chemical_name_systematic 'N-(1-(1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-5-yl) benzophenone imine' _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary intrinsic _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-10-06 deposited with the CCDC. 2021-10-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.736(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.3648(10) _cell_length_b 8.5788(8) _cell_length_c 10.6319(9) _cell_measurement_reflns_used 5644 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 25.26 _cell_measurement_theta_min 2.52 _cell_volume 928.81(15) _computing_cell_refinement 'SAINT V8.37A (Bruker, 2005)' _computing_data_collection 'APEX3 V2016.5-0 (Bruker, 2016)' _computing_data_reduction ; SAINT V8.37A, XPREP v2014/2, TWINABS V2012/1 (Bruker, 2016) ; _computing_molecular_graphics 'SHELXLE v932 (Hubschle, 2011)' _computing_publication_material 'XCIF V2014-2 (Bruker, 2014)' _computing_structure_refinement 'SHELX-2018-3 (Sheldrick, 2015)' _computing_structure_solution 'SHELX-2014-5 (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Bruker D8 Quest/Photon 100' _diffrn_measurement_method 'profile data from \f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_source 'microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.0548 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2935 _diffrn_reflns_point_group_measured_fraction_full 0.536 _diffrn_reflns_point_group_measured_fraction_max 0.536 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.294 _diffrn_reflns_theta_min 2.000 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 0.745210 _exptl_absorpt_correction_T_min 0.593114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2016/2 (Bruker, 2016)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 360 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Diethyl ether' _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.205 _exptl_crystal_size_min 0.078 _refine_diff_density_max 0.327 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.075 _refine_ls_abs_structure_details ; No quotients, so Flack parameter determined by classical intensity fit ; _refine_ls_abs_structure_Flack 2(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 2935 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.153 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0614 _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^)+(0.0173P)^2^+1.4074P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1225 _refine_ls_wR_factor_ref 0.1428 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full 0.000 _reflns_Friedel_fraction_max 0.000 _reflns_number_gt 2474 _reflns_number_total 2935 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03578a2.cif _cod_data_source_block twin5 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1565129 _shelx_shelxl_version_number 2018/3 _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_estimated_absorpt_t_min 0.985 _shelx_estimated_absorpt_t_max 0.994 _shelx_res_file ; TITL twin4_a.res in P2(1) twin5.res created by SHELXL-2018/3 at 09:34:54 on 01-Oct-2020 REM Old TITL twin4 in P2(1) REM SHELXT solution in P2(1) REM R1 0.306, Rweak 0.199, Alpha 0.058, Orientation as input REM Formula found by SHELXT: C23 N O CELL 0.71073 10.3648 8.5788 10.6319 90.000 100.736 90.000 ZERR 2.000 0.0010 0.0008 0.0009 0.000 0.004 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H N O UNIT 46 54 2 2 TEMP -173.130 SIZE 0.078 0.205 0.21 L.S. 20 CONF ACTA BOND $H LIST 4 FMAP 2 PLAN 20 WGHT 0.017300 1.407400 BASF 0.50278 FVAR 1.65098 O1 4 0.638259 0.767601 0.352788 11.00000 0.02338 0.01964 = 0.01568 -0.00277 -0.00004 -0.00164 N1 3 0.328678 0.467355 0.205567 11.00000 0.02173 0.02033 = 0.02138 -0.00188 0.00302 -0.00199 C1 1 0.578014 0.794560 0.219307 11.00000 0.02294 0.02423 = 0.01813 0.00124 0.00516 -0.00567 C2 1 0.502970 0.646432 0.167361 11.00000 0.02101 0.02868 = 0.01745 -0.00148 0.00152 -0.00345 AFIX 13 H2 2 0.452124 0.665364 0.079123 11.00000 -1.20000 AFIX 0 C3 1 0.408969 0.601711 0.258657 11.00000 0.01847 0.02320 = 0.01794 -0.00719 0.00306 -0.00460 AFIX 13 H3 2 0.350589 0.692009 0.268330 11.00000 -1.20000 AFIX 0 C4 1 0.493052 0.560185 0.389922 11.00000 0.02231 0.03478 = 0.01923 -0.00546 0.00698 -0.00897 AFIX 23 H4A 2 0.459003 0.615759 0.458546 11.00000 -1.20000 H4B 2 0.487573 0.446779 0.405348 11.00000 -1.20000 AFIX 0 C5 1 0.635077 0.606075 0.393001 11.00000 0.02390 0.02480 = 0.02108 0.00121 0.00232 -0.00122 C6 1 0.692001 0.504882 0.299376 11.00000 0.02378 0.02392 = 0.02569 -0.00232 0.00448 0.00519 AFIX 23 H6A 2 0.699964 0.395944 0.330584 11.00000 -1.20000 H6B 2 0.780739 0.542721 0.292812 11.00000 -1.20000 AFIX 0 C7 1 0.601156 0.511150 0.165928 11.00000 0.02243 0.02301 = 0.02940 -0.00162 0.00682 0.00134 AFIX 23 H7A 2 0.653847 0.528931 0.098571 11.00000 -1.20000 H7B 2 0.553324 0.411359 0.147850 11.00000 -1.20000 AFIX 0 C8 1 0.686186 0.838764 0.145697 11.00000 0.02773 0.03094 = 0.02369 0.00155 0.00553 0.00022 AFIX 137 H8A 2 0.646958 0.861405 0.056409 11.00000 -1.50000 H8B 2 0.748157 0.751967 0.148705 11.00000 -1.50000 H8C 2 0.732738 0.931238 0.184821 11.00000 -1.50000 AFIX 0 C9 1 0.488677 0.936727 0.218096 11.00000 0.03048 0.02783 = 0.03343 0.00234 0.00904 0.00355 AFIX 137 H9A 2 0.540875 1.026152 0.255687 11.00000 -1.50000 H9B 2 0.420509 0.914008 0.268143 11.00000 -1.50000 H9C 2 0.447422 0.961088 0.129681 11.00000 -1.50000 AFIX 0 C10 1 0.718066 0.600485 0.526091 11.00000 0.03089 0.03703 = 0.01967 0.00381 0.00623 -0.00217 AFIX 137 H10A 2 0.807954 0.632966 0.522492 11.00000 -1.50000 H10B 2 0.719062 0.493892 0.559405 11.00000 -1.50000 H10C 2 0.680914 0.670978 0.582547 11.00000 -1.50000 AFIX 0 C11 1 0.212990 0.455194 0.235085 11.00000 0.01745 0.01730 = 0.01405 -0.00120 -0.00077 0.00334 C12 1 0.131608 0.318257 0.183281 11.00000 0.02374 0.01545 = 0.01492 0.00260 0.00196 -0.00382 C13 1 0.188207 0.188052 0.137105 11.00000 0.01986 0.01967 = 0.02092 0.00380 0.00299 0.00685 AFIX 43 H13 2 0.280245 0.185619 0.139366 11.00000 -1.20000 AFIX 0 C14 1 0.111607 0.062288 0.087996 11.00000 0.03735 0.01623 = 0.02353 -0.00542 0.00708 -0.00459 AFIX 43 H14 2 0.151693 -0.026055 0.057480 11.00000 -1.20000 AFIX 0 C15 1 -0.024026 0.063721 0.082770 11.00000 0.02589 0.03295 = 0.01585 -0.00438 0.00281 -0.01304 AFIX 43 H15 2 -0.076436 -0.022454 0.048168 11.00000 -1.20000 AFIX 0 C16 1 -0.080931 0.192425 0.128703 11.00000 0.01728 0.02736 = 0.01817 0.00071 0.00062 -0.00280 AFIX 43 H16 2 -0.173144 0.195452 0.125267 11.00000 -1.20000 AFIX 0 C17 1 -0.002827 0.317766 0.180071 11.00000 0.02410 0.01775 = 0.01587 0.00050 0.00714 -0.00140 AFIX 43 H17 2 -0.042433 0.404469 0.213505 11.00000 -1.20000 AFIX 0 C18 1 0.158136 0.563400 0.320555 11.00000 0.01908 0.02062 = 0.01847 0.00106 0.00178 -0.00530 C19 1 0.186138 0.539990 0.453230 11.00000 0.01969 0.02013 = 0.02113 0.00037 0.00668 -0.00092 AFIX 43 H19 2 0.240003 0.455207 0.488356 11.00000 -1.20000 AFIX 0 C20 1 0.134858 0.641185 0.533196 11.00000 0.01978 0.02131 = 0.01973 -0.00124 0.00712 -0.00605 AFIX 43 H20 2 0.153939 0.624790 0.623120 11.00000 -1.20000 AFIX 0 C21 1 0.056274 0.765737 0.483928 11.00000 0.02417 0.02508 = 0.02565 -0.00545 0.01007 0.00180 AFIX 43 H21 2 0.021452 0.833932 0.539603 11.00000 -1.20000 AFIX 0 C22 1 0.029083 0.789841 0.353649 11.00000 0.02201 0.01762 = 0.02841 0.00053 -0.00059 0.01012 AFIX 43 H22 2 -0.024576 0.875317 0.319700 11.00000 -1.20000 AFIX 0 C23 1 0.079165 0.690666 0.271179 11.00000 0.02819 0.01983 = 0.01812 -0.00042 0.00265 -0.00360 AFIX 43 H23 2 0.060054 0.708846 0.181488 11.00000 -1.20000 AFIX 0 HKLF 5 REM twin4_a.res in P2(1) REM wR2 = 0.142836, GooF = S = 1.15290, Restrained GooF = 1.15269 for all data REM R1 = 0.061402 for 2474 Fo > 4sig(Fo) and 0.094836 for all 2935 data REM 230 parameters refined using 1 restraints END WGHT 0.0171 1.4109 REM Highest difference peak 0.327, deepest hole -0.289, 1-sigma level 0.075 Q1 1 -0.0114 0.7442 0.0636 11.00000 0.05 0.33 Q2 1 0.4450 0.6266 0.2059 11.00000 0.05 0.30 Q3 1 0.6425 0.8252 -0.0218 11.00000 0.05 0.27 Q4 1 -0.2234 0.1925 0.1093 11.00000 0.05 0.27 Q5 1 0.1771 0.3055 0.0197 11.00000 0.05 0.27 Q6 1 -0.2769 0.1635 -0.0215 11.00000 0.05 0.27 Q7 1 0.3867 0.8265 0.2933 11.00000 0.05 0.26 Q8 1 0.7735 0.9497 0.2048 11.00000 0.05 0.26 Q9 1 0.3052 0.6080 0.6768 11.00000 0.05 0.26 Q10 1 0.1209 0.5912 0.6863 11.00000 0.05 0.25 Q11 1 0.3051 0.8820 0.0365 11.00000 0.05 0.24 Q12 1 0.8234 0.4557 0.4662 11.00000 0.05 0.24 Q13 1 0.0568 0.6861 0.6630 11.00000 0.05 0.24 Q14 1 0.3407 0.5776 0.4663 11.00000 0.05 0.24 Q15 1 0.4142 0.8287 0.4442 11.00000 0.05 0.24 Q16 1 0.4877 0.9069 0.0561 11.00000 0.05 0.24 Q17 1 0.6072 1.0649 0.3740 11.00000 0.05 0.24 Q18 1 0.5897 0.4484 0.0429 11.00000 0.05 0.23 Q19 1 0.2731 0.4898 0.4854 11.00000 0.05 0.23 Q20 1 0.5913 0.9505 0.0217 11.00000 0.05 0.23 ; _shelx_res_checksum 47817 _shelx_hkl_file ; 1 0 0 0.83542 4.20515 2 1 0 0 -0.5470 3.74274 1 2 0 0 1022.43 14.3426 2 2 0 0 989.506 13.4540 1 -3 0 1 111.404 3.44058 -2 3 0 0 111.404 3.44058 1 3 0 0 87.4327 2.67069 2 3 0 0 82.9564 3.01760 1 4 0 0 153.860 3.19620 1 4 0 0 158.333 3.16949 2 -5 0 2 2080.76 28.0150 -2 5 0 0 2080.76 28.0150 1 6 0 0 869.671 20.3985 1 6 0 0 888.409 25.2174 2 -6 0 2 1070.20 40.3217 -2 6 0 0 1070.20 40.3217 1 7 0 0 37.1860 7.44577 1 -7 0 3 45.9948 7.46308 -2 7 0 0 45.9948 7.46308 1 7 0 0 40.3466 6.02184 2 -8 0 3 173.579 8.81905 -2 8 0 0 173.579 8.81905 1 9 0 0 54.8840 5.91965 2 9 0 0 84.0368 7.17118 1 -10 0 4 163.962 12.3376 -2 10 0 0 163.962 12.3376 1 -11 0 4 331.259 16.6914 -2 11 0 0 331.259 16.6914 1 -12 0 5 27.1320 20.3715 -2 12 0 0 27.1320 20.3715 1 12 0 0 69.1893 111.065 2 0 1 0 0.18203 0.30163 1 1 1 0 1525.90 17.5088 2 1 1 0 1549.54 18.8123 1 2 1 0 4646.95 58.0477 1 2 1 0 4730.71 55.9331 2 -2 1 1 8179.21 174.944 -2 2 1 0 8179.21 174.944 1 -3 1 1 2343.30 26.9109 -2 3 1 0 2343.30 26.9109 1 3 1 0 1356.58 24.4949 1 3 1 0 1451.35 51.3891 2 4 1 0 405.793 4.73678 1 4 1 0 413.058 4.70248 2 -5 1 2 1420.81 16.6593 -2 5 1 0 1420.81 16.6593 1 -6 1 2 269.320 12.0001 -2 6 1 0 269.320 12.0001 1 6 1 0 78.3380 3.02794 1 6 1 0 72.2457 2.70579 2 -7 1 3 379.387 9.78526 -2 7 1 0 379.387 9.78526 1 7 1 0 180.073 8.97104 1 7 1 0 185.028 5.87183 2 -8 1 3 65.4594 4.95083 -2 8 1 0 65.4594 4.95083 1 9 1 0 -2.5241 3.28283 1 9 1 0 14.8322 3.36127 2 -9 1 3 221.506 14.0295 -2 9 1 0 221.506 14.0295 1 -10 1 4 236.915 8.85745 -2 10 1 0 236.915 8.85745 1 -11 1 4 107.434 10.5481 -2 11 1 0 107.434 10.5481 1 -12 1 5 97.0178 14.2053 -2 12 1 0 97.0178 14.2053 1 12 1 0 -61.594 113.859 2 0 2 0 5181.54 72.9869 -2 0 2 0 5181.54 72.9869 1 1 2 0 2054.19 21.8339 2 1 2 0 2018.02 21.0085 1 2 2 0 942.911 13.6693 1 2 2 0 948.337 12.5327 2 -2 2 1 1275.09 21.5378 -2 2 2 0 1275.09 21.5378 1 -3 2 1 2705.46 29.6088 -2 3 2 0 2705.46 29.6088 1 4 2 0 425.654 6.09233 1 4 2 0 416.606 6.26628 2 -5 2 2 632.799 8.50400 -2 5 2 0 632.799 8.50400 1 -6 2 2 582.026 15.6556 -2 6 2 0 582.026 15.6556 1 6 2 0 185.678 5.02467 1 6 2 0 179.864 6.15529 2 7 2 0 22.6555 3.71101 1 7 2 0 30.5113 5.00665 2 -7 2 3 222.462 10.1097 -2 7 2 0 222.462 10.1097 1 -8 2 3 243.934 6.37707 -2 8 2 0 243.934 6.37707 1 9 2 0 207.318 7.85308 1 9 2 0 198.878 8.68400 2 -9 2 3 266.683 21.9664 -2 9 2 0 266.683 21.9664 1 -10 2 4 147.477 8.52738 -2 10 2 0 147.477 8.52738 1 -11 2 4 132.978 10.6567 -2 11 2 0 132.978 10.6567 1 12 2 0 10.3785 6.92184 1 12 2 0 14.6498 6.45724 2 0 3 0 1.16137 0.86895 1 1 3 0 242.546 3.37560 2 1 3 0 233.541 3.58429 1 2 3 0 178.364 3.69450 1 -2 3 1 1999.15 36.9391 -2 2 3 0 1999.15 36.9391 1 2 3 0 179.465 3.97240 2 -3 3 1 2783.23 33.9957 -2 3 3 0 2783.23 33.9957 1 4 3 0 1704.97 23.9691 2 4 3 0 1688.15 21.1236 1 -5 3 2 192.612 5.17638 -2 5 3 0 192.612 5.17638 1 -6 3 2 807.964 18.0973 -2 6 3 0 807.964 18.0973 1 6 3 0 456.996 12.3406 2 6 3 0 443.804 20.8420 1 -7 3 3 646.864 15.8062 -2 7 3 0 646.864 15.8062 1 7 3 0 331.301 19.4824 1 7 3 0 348.995 11.0807 2 -8 3 3 233.955 7.91269 -2 8 3 0 233.955 7.91269 1 9 3 0 67.0911 7.06918 1 9 3 0 42.9858 4.41092 2 -9 3 3 244.084 24.3767 -2 9 3 0 244.084 24.3767 1 -10 3 4 111.734 9.51590 -2 10 3 0 111.734 9.51590 1 -11 3 4 10.7235 13.9411 -2 11 3 0 10.7235 13.9411 1 0 4 0 1978.93 28.4966 -2 0 4 0 1978.93 28.4966 1 1 4 0 119.698 2.50146 2 1 4 0 120.623 2.70157 1 2 4 0 223.788 6.10977 2 -2 4 1 1313.88 21.6819 -2 2 4 0 1313.88 21.6819 1 2 4 0 220.619 7.13631 1 -3 4 1 1105.38 15.9785 -2 3 4 0 1105.38 15.9785 1 4 4 0 69.6853 3.70539 1 4 4 0 70.8977 3.16835 2 -5 4 2 596.559 12.0506 -2 5 4 0 596.559 12.0506 1 -6 4 2 205.361 8.16617 -2 6 4 0 205.361 8.16617 1 6 4 0 67.8210 28.7658 2 6 4 0 134.271 49.3759 1 -7 4 3 1015.59 20.2275 -2 7 4 0 1015.59 20.2275 1 7 4 0 666.218 76.2677 1 -8 4 3 573.847 13.1249 -2 8 4 0 573.847 13.1249 1 9 4 0 8.88955 4.70659 2 -9 4 3 279.409 25.1751 -2 9 4 0 279.409 25.1751 1 9 4 0 -0.2507 6.13241 1 -10 4 4 83.0504 10.9342 -2 10 4 0 83.0504 10.9342 1 -11 4 4 -46.247 14.4839 -2 11 4 0 -46.247 14.4839 1 0 5 0 7.67464 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59.4266 7.82722 1 -1 2 10 12.2724 4.26646 2 -1 2 10 8.85697 3.30996 1 0 2 10 246.713 7.74252 -2 0 2 10 246.713 7.74252 1 1 2 10 91.7143 7.15232 1 1 2 10 91.9490 6.33492 2 -1 2 10 103.825 20.5940 -2 1 2 10 103.825 20.5940 1 -2 2 11 27.6087 8.95153 -2 2 2 10 27.6087 8.95153 1 -3 2 11 88.1820 8.79955 -2 3 2 10 88.1820 8.79955 1 4 2 10 40.9431 5.84363 1 4 2 10 21.9609 4.90225 2 -5 2 12 160.052 11.3467 -2 5 2 10 160.052 11.3467 1 8 3 7 47.2489 10.6474 -2 -8 3 10 47.2489 10.6474 1 7 3 7 48.7072 12.4341 -2 -7 3 10 48.7072 12.4341 1 6 3 8 43.8601 11.5449 -2 -6 3 10 43.8601 11.5449 1 -6 3 10 24.1096 38.3938 2 5 3 8 261.005 10.4337 -2 -5 3 10 261.005 10.4337 1 -4 3 10 22.3323 4.23578 2 -4 3 10 20.0339 4.14486 1 3 3 9 143.849 7.12677 -2 -3 3 10 143.849 7.12677 1 2 3 9 266.472 10.3792 -2 -2 3 10 266.472 10.3792 1 -1 3 10 441.992 10.5961 1 -1 3 10 425.419 10.4788 2 1 3 10 488.948 33.6087 -2 -1 3 10 488.948 33.6087 1 0 3 10 450.986 10.2415 -2 0 3 10 450.986 10.2415 1 1 3 10 41.6632 4.42456 2 1 3 10 36.9828 5.12974 1 -1 3 10 679.960 173.066 -2 1 3 10 679.960 173.066 1 -2 3 11 176.730 10.5470 -2 2 3 10 176.730 10.5470 1 -3 3 11 21.4618 8.58466 -2 3 3 10 21.4618 8.58466 1 4 3 10 32.2741 5.13693 1 4 3 10 49.3786 6.50536 2 7 4 7 53.1295 13.8988 -2 -7 4 10 53.1295 13.8988 1 6 4 8 37.7045 15.1919 -2 -6 4 10 37.7045 15.1919 1 -6 4 10 33.7532 39.6465 2 5 4 8 139.833 9.94100 -2 -5 4 10 139.833 9.94100 1 -4 4 10 65.3593 6.54638 2 -4 4 10 68.6046 5.72632 1 3 4 9 83.1163 11.9247 -2 -3 4 10 83.1163 11.9247 1 2 4 9 220.090 11.2752 -2 -2 4 10 220.090 11.2752 1 -1 4 10 1.66780 3.73306 2 -1 4 10 -3.6839 4.32693 1 1 4 10 95.9779 28.1161 -2 -1 4 10 95.9779 28.1161 1 0 4 10 33.5782 4.98710 -2 0 4 10 33.5782 4.98710 1 -1 4 10 135.953 27.7465 -2 1 4 10 135.953 27.7465 1 1 4 10 129.729 7.99713 2 1 4 10 134.723 9.32402 1 -2 4 11 88.8848 11.6854 -2 2 4 10 88.8848 11.6854 1 -3 4 11 353.662 12.3066 -2 3 4 10 353.662 12.3066 1 4 4 10 43.4192 7.35014 2 4 4 10 39.1262 5.96237 1 6 5 8 55.1989 14.2608 -2 -6 5 10 55.1989 14.2608 1 5 5 8 70.9020 9.97373 -2 -5 5 10 70.9020 9.97373 1 -4 5 10 99.6147 8.38908 1 -4 5 10 72.7916 7.35930 2 3 5 9 102.744 13.2342 -2 -3 5 10 102.744 13.2342 1 2 5 9 209.929 15.0542 -2 -2 5 10 209.929 15.0542 1 -1 5 10 101.276 6.02657 2 -1 5 10 96.1817 6.86452 1 1 5 10 208.964 34.1737 -2 -1 5 10 208.964 34.1737 1 0 5 10 420.789 11.3952 -2 0 5 10 420.789 11.3952 1 1 5 10 43.0202 5.62940 2 1 5 10 27.7903 4.91935 1 -1 5 10 152.312 32.8984 -2 1 5 10 152.312 32.8984 1 -2 5 11 274.216 14.0548 -2 2 5 10 274.216 14.0548 1 -4 6 10 11.7411 6.73022 2 -4 6 10 2.29475 7.13663 1 3 6 9 39.4752 13.7165 -2 -3 6 10 39.4752 13.7165 1 2 6 9 63.4652 18.0189 -2 -2 6 10 63.4652 18.0189 1 -1 6 10 4.02549 5.51739 1 -1 6 10 3.53081 4.36557 2 0 6 10 13.4172 5.99409 -2 0 6 10 13.4172 5.99409 1 8 0 8 147.279 16.8707 -2 -8 0 11 147.279 16.8707 1 7 0 8 222.208 23.1195 -2 -7 0 11 222.208 23.1195 1 6 0 9 134.338 20.8387 -2 -6 0 11 134.338 20.8387 1 5 0 9 104.305 11.4985 -2 -5 0 11 104.305 11.4985 1 -4 0 11 -2.7686 5.48416 1 -4 0 11 49.6748 10.3681 2 3 0 10 96.1114 9.63956 -2 -3 0 11 96.1114 9.63956 1 2 0 10 46.2075 10.6386 -2 -2 0 11 46.2075 10.6386 1 -1 0 11 85.5565 8.74537 2 -1 0 11 100.959 6.15160 1 1 0 11 63.4236 104.834 -2 -1 0 11 63.4236 104.834 1 0 0 11 71.0452 7.40296 -2 0 0 11 71.0452 7.40296 1 1 0 11 41.5210 8.69839 1 1 0 11 66.3563 5.98199 2 -2 0 12 273.510 21.2254 -2 2 0 11 273.510 21.2254 1 -3 0 12 178.687 18.5370 -2 3 0 11 178.687 18.5370 1 4 0 11 61.1101 9.96968 1 4 0 11 68.6803 7.95743 2 8 1 8 114.553 11.9250 -2 -8 1 11 114.553 11.9250 1 7 1 8 138.963 14.4559 -2 -7 1 11 138.963 14.4559 1 6 1 9 118.989 13.3178 -2 -6 1 11 118.989 13.3178 1 5 1 9 57.0462 7.24842 -2 -5 1 11 57.0462 7.24842 1 -4 1 11 29.5608 4.20043 2 -4 1 11 34.8213 4.09265 1 3 1 10 46.0114 10.5929 -2 -3 1 11 46.0114 10.5929 1 2 1 10 161.147 8.00945 -2 -2 1 11 161.147 8.00945 1 -1 1 11 4.21467 4.80505 2 -1 1 11 13.5593 3.65572 1 0 1 11 67.6750 5.52665 -2 0 1 11 67.6750 5.52665 1 1 1 11 2.08461 5.11304 1 1 1 11 13.5535 4.33525 2 -2 1 12 29.2913 12.7113 -2 2 1 11 29.2913 12.7113 1 -3 1 12 95.0108 12.3320 -2 3 1 11 95.0108 12.3320 1 4 1 11 6.29790 5.86863 2 4 1 11 3.81033 6.17285 1 7 2 8 48.5542 14.2437 -2 -7 2 11 48.5542 14.2437 1 6 2 9 123.389 13.9080 -2 -6 2 11 123.389 13.9080 1 5 2 9 56.8515 8.27244 -2 -5 2 11 56.8515 8.27244 1 -4 2 11 21.1940 4.36414 1 -4 2 11 12.6123 4.25749 2 4 2 9 41.7417 28.1671 -2 -4 2 11 41.7417 28.1671 1 3 2 10 63.0551 7.86466 -2 -3 2 11 63.0551 7.86466 1 2 2 10 30.8645 8.77419 -2 -2 2 11 30.8645 8.77419 1 1 2 11 145.685 18.7651 -2 -1 2 11 145.685 18.7651 1 -1 2 11 92.0012 6.43470 2 -1 2 11 82.7913 7.00379 1 0 2 11 60.1530 6.31266 -2 0 2 11 60.1530 6.31266 1 1 2 11 7.61419 5.25519 2 1 2 11 -3.1359 5.33185 1 -1 2 11 121.847 22.7892 -2 1 2 11 121.847 22.7892 1 -2 2 12 26.0860 13.1199 -2 2 2 11 26.0860 13.1199 1 -3 2 12 67.3398 11.2880 -2 3 2 11 67.3398 11.2880 1 7 3 8 109.631 16.6488 -2 -7 3 11 109.631 16.6488 1 6 3 9 22.7356 14.9943 -2 -6 3 11 22.7356 14.9943 1 5 3 9 275.506 11.3468 -2 -5 3 11 275.506 11.3468 1 -4 3 11 3.68244 4.53279 1 -4 3 11 5.17836 4.46008 2 3 3 10 18.9667 11.6416 -2 -3 3 11 18.9667 11.6416 1 2 3 10 186.030 10.6947 -2 -2 3 11 186.030 10.6947 1 -1 3 11 26.0911 5.20824 2 -1 3 11 15.6852 4.66573 1 1 3 11 96.3973 20.6384 -2 -1 3 11 96.3973 20.6384 1 0 3 11 67.3240 5.47219 -2 0 3 11 67.3240 5.47219 1 1 3 11 29.7631 5.13343 2 1 3 11 27.1302 5.47410 1 -1 3 11 12.8541 25.5039 -2 1 3 11 12.8541 25.5039 1 -2 3 12 38.4960 11.2751 -2 2 3 11 38.4960 11.2751 1 -3 3 12 17.8081 10.7346 -2 3 3 11 17.8081 10.7346 1 -6 4 11 108.781 8.69819 2 -6 4 11 108.697 7.51809 1 5 4 9 99.2748 12.9086 -2 -5 4 11 99.2748 12.9086 1 -4 4 11 50.8060 5.94529 2 -4 4 11 56.8959 7.41548 1 3 4 10 375.363 16.5259 -2 -3 4 11 375.363 16.5259 1 2 4 10 99.9470 12.6185 -2 -2 4 11 99.9470 12.6185 1 -1 4 11 118.688 7.76354 1 -1 4 11 104.735 7.95362 2 1 4 11 265.051 35.0876 -2 -1 4 11 265.051 35.0876 1 0 4 11 280.248 10.1177 -2 0 4 11 280.248 10.1177 1 1 4 11 45.3242 6.80831 1 1 4 11 45.7733 5.98497 2 -1 4 11 148.751 33.1874 -2 1 4 11 148.751 33.1874 1 2 4 11 12.5731 5.91389 2 2 4 11 1.26137 6.26479 1 -3 5 11 54.9298 5.58574 2 -3 5 11 62.0020 7.68081 1 2 5 10 233.072 19.3530 -2 -2 5 11 233.072 19.3530 1 -1 5 11 29.9901 5.99383 2 -1 5 11 32.5326 5.82214 1 -6 0 12 83.0010 9.45886 1 -6 0 12 73.9666 11.0437 2 5 0 10 -7.9815 16.4435 -2 -5 0 12 -7.9815 16.4435 1 -4 0 12 28.3306 9.68141 2 -4 0 12 43.5550 7.21370 1 3 0 11 181.982 12.7205 -2 -3 0 12 181.982 12.7205 1 2 0 11 219.846 18.0957 -2 -2 0 12 219.846 18.0957 1 -1 0 12 26.7639 8.43139 1 -1 0 12 11.3780 8.16408 2 0 0 12 9.29300 8.41165 -2 0 0 12 9.29300 8.41165 1 1 0 12 1.22109 8.41549 2 1 0 12 -0.7134 8.07907 1 2 0 12 63.0835 10.4683 1 2 0 12 53.9131 10.0316 2 -6 1 12 71.8170 6.95653 1 -6 1 12 53.0034 6.81397 2 5 1 10 50.3113 8.75850 -2 -5 1 12 50.3113 8.75850 1 -4 1 12 2.35329 4.18522 1 -4 1 12 2.19122 5.78000 2 3 1 11 116.309 10.6870 -2 -3 1 12 116.309 10.6870 1 2 1 11 11.2535 10.7839 -2 -2 1 12 11.2535 10.7839 1 -1 1 12 1.60839 5.63071 2 -1 1 12 12.2074 4.62319 1 0 1 12 -3.7938 5.71633 -2 0 1 12 -3.7938 5.71633 1 1 1 12 -1.5213 5.81754 1 1 1 12 0.99134 5.76734 2 5 2 10 181.535 10.2283 -2 -5 2 12 181.535 10.2283 1 -4 2 12 15.1913 5.47526 1 -4 2 12 3.42007 5.52817 2 3 2 11 65.9505 11.2442 -2 -3 2 12 65.9505 11.2442 1 2 2 11 32.1821 10.0728 -2 -2 2 12 32.1821 10.0728 1 1 2 12 106.931 14.9700 -2 -1 2 12 106.931 14.9700 1 -1 2 12 55.8540 6.33411 2 -1 2 12 48.6258 7.49954 1 0 2 12 10.3150 5.37624 -2 0 2 12 10.3150 5.37624 1 -1 2 12 93.2913 22.7911 -2 1 2 12 93.2913 22.7911 1 1 2 12 51.9220 9.57902 2 1 2 12 31.5279 7.45715 1 -4 3 12 7.34652 5.87538 1 -4 3 12 3.14463 5.71757 2 3 3 11 20.6732 11.6856 -2 -3 3 12 20.6732 11.6856 1 2 3 11 23.0950 12.5523 -2 -2 3 12 23.0950 12.5523 1 -1 3 12 13.4870 5.15304 2 -1 3 12 14.9574 4.62002 1 0 3 12 431.560 12.1815 -2 0 3 12 431.560 12.1815 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 72108 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -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 0.6383(4) 0.7676(5) 0.3528(4) 0.0200(10) Uani 1 1 d . . . . . N1 N 0.3287(5) 0.4674(6) 0.2056(5) 0.0213(12) Uani 1 1 d . . . . . C1 C 0.5780(6) 0.7946(8) 0.2193(5) 0.0216(14) Uani 1 1 d . . . . . C2 C 0.5030(6) 0.6464(8) 0.1674(6) 0.0226(15) Uani 1 1 d . . . . . H2 H 0.452124 0.665364 0.079123 0.027 Uiso 1 1 calc R U . . . C3 C 0.4090(6) 0.6017(8) 0.2587(6) 0.0199(14) Uani 1 1 d . . . . . H3 H 0.350589 0.692009 0.268330 0.024 Uiso 1 1 calc R U . . . C4 C 0.4931(6) 0.5602(9) 0.3899(6) 0.0250(16) Uani 1 1 d . . . . . H4A H 0.459003 0.615759 0.458546 0.030 Uiso 1 1 calc R U . . . H4B H 0.487573 0.446779 0.405348 0.030 Uiso 1 1 calc R U . . . C5 C 0.6351(6) 0.6061(8) 0.3930(6) 0.0235(16) Uani 1 1 d . . . . . C6 C 0.6920(6) 0.5049(8) 0.2994(6) 0.0245(15) Uani 1 1 d . . . . . H6A H 0.699964 0.395944 0.330584 0.029 Uiso 1 1 calc R U . . . H6B H 0.780739 0.542721 0.292812 0.029 Uiso 1 1 calc R U . . . C7 C 0.6012(6) 0.5111(9) 0.1659(6) 0.0247(16) Uani 1 1 d . . . . . H7A H 0.653847 0.528931 0.098571 0.030 Uiso 1 1 calc R U . . . H7B H 0.553324 0.411359 0.147850 0.030 Uiso 1 1 calc R U . . . C8 C 0.6862(6) 0.8388(9) 0.1457(6) 0.0274(17) Uani 1 1 d . . . . . H8A H 0.646958 0.861405 0.056409 0.041 Uiso 1 1 calc R U . . . H8B H 0.748157 0.751967 0.148705 0.041 Uiso 1 1 calc R U . . . H8C H 0.732738 0.931238 0.184821 0.041 Uiso 1 1 calc R U . . . C9 C 0.4887(7) 0.9367(9) 0.2181(7) 0.0302(16) Uani 1 1 d . . . . . H9A H 0.540875 1.026152 0.255687 0.045 Uiso 1 1 calc R U . . . H9B H 0.420509 0.914008 0.268143 0.045 Uiso 1 1 calc R U . . . H9C H 0.447422 0.961088 0.129681 0.045 Uiso 1 1 calc R U . . . C10 C 0.7181(6) 0.6005(9) 0.5261(6) 0.0290(17) Uani 1 1 d . . . . . H10A H 0.807954 0.632966 0.522492 0.044 Uiso 1 1 calc R U . . . H10B H 0.719062 0.493892 0.559405 0.044 Uiso 1 1 calc R U . . . H10C H 0.680914 0.670978 0.582547 0.044 Uiso 1 1 calc R U . . . C11 C 0.2130(6) 0.4552(8) 0.2351(5) 0.0167(14) Uani 1 1 d . . . . . C12 C 0.1316(6) 0.3183(8) 0.1833(6) 0.0182(13) Uani 1 1 d . . . . . C13 C 0.1882(6) 0.1881(8) 0.1371(6) 0.0203(14) Uani 1 1 d . . . . . H13 H 0.280245 0.185619 0.139366 0.024 Uiso 1 1 calc R U . . . C14 C 0.1116(7) 0.0623(8) 0.0880(6) 0.0255(16) Uani 1 1 d . . . . . H14 H 0.151693 -0.026055 0.057480 0.031 Uiso 1 1 calc R U . . . C15 C -0.0240(6) 0.0637(9) 0.0828(6) 0.0250(15) Uani 1 1 d . . . . . H15 H -0.076436 -0.022454 0.048168 0.030 Uiso 1 1 calc R U . . . C16 C -0.0809(6) 0.1924(8) 0.1287(6) 0.0213(15) Uani 1 1 d . . . . . H16 H -0.173144 0.195452 0.125267 0.026 Uiso 1 1 calc R U . . . C17 C -0.0028(6) 0.3178(8) 0.1801(5) 0.0188(13) Uani 1 1 d . . . . . H17 H -0.042433 0.404469 0.213505 0.023 Uiso 1 1 calc R U . . . C18 C 0.1581(6) 0.5634(8) 0.3206(6) 0.0196(14) Uani 1 1 d . . . . . C19 C 0.1861(6) 0.5400(8) 0.4532(6) 0.0199(14) Uani 1 1 d . . . . . H19 H 0.240003 0.455207 0.488356 0.024 Uiso 1 1 calc R U . . . C20 C 0.1349(6) 0.6412(7) 0.5332(6) 0.0198(14) Uani 1 1 d . . . . . H20 H 0.153939 0.624790 0.623120 0.024 Uiso 1 1 calc R U . . . C21 C 0.0563(6) 0.7657(8) 0.4839(6) 0.0243(15) Uani 1 1 d . . . . . H21 H 0.021452 0.833932 0.539603 0.029 Uiso 1 1 calc R U . . . C22 C 0.0291(6) 0.7898(8) 0.3536(6) 0.0234(14) Uani 1 1 d . . . . . H22 H -0.024576 0.875317 0.319700 0.028 Uiso 1 1 calc R U . . . C23 C 0.0792(6) 0.6907(8) 0.2712(6) 0.0223(14) Uani 1 1 d . . . . . H23 H 0.060054 0.708846 0.181488 0.027 Uiso 1 1 calc R U . . . 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 0.023(2) 0.020(2) 0.016(2) -0.0028(19) 0.0000(19) -0.002(2) N1 0.022(3) 0.020(3) 0.021(3) -0.002(2) 0.003(2) -0.002(3) C1 0.023(3) 0.024(4) 0.018(3) 0.001(3) 0.005(3) -0.006(3) C2 0.021(3) 0.029(4) 0.017(3) -0.001(3) 0.002(3) -0.003(3) C3 0.018(3) 0.023(4) 0.018(3) -0.007(3) 0.003(3) -0.005(3) C4 0.022(3) 0.035(4) 0.019(3) -0.005(3) 0.007(3) -0.009(3) C5 0.024(3) 0.025(4) 0.021(3) 0.001(3) 0.002(3) -0.001(3) C6 0.024(3) 0.024(4) 0.026(3) -0.002(3) 0.004(3) 0.005(3) C7 0.022(4) 0.023(4) 0.029(4) -0.002(3) 0.007(3) 0.001(3) C8 0.028(4) 0.031(4) 0.024(3) 0.002(3) 0.006(3) 0.000(4) C9 0.030(4) 0.028(4) 0.033(4) 0.002(3) 0.009(3) 0.004(4) C10 0.031(4) 0.037(4) 0.020(3) 0.004(3) 0.006(3) -0.002(4) C11 0.017(3) 0.017(3) 0.014(3) -0.001(3) -0.001(3) 0.003(3) C12 0.024(3) 0.015(3) 0.015(3) 0.003(3) 0.002(3) -0.004(3) C13 0.020(3) 0.020(4) 0.021(3) 0.004(3) 0.003(3) 0.007(3) C14 0.037(4) 0.016(3) 0.024(3) -0.005(3) 0.007(3) -0.005(3) C15 0.026(4) 0.033(4) 0.016(3) -0.004(3) 0.003(3) -0.013(4) C16 0.017(3) 0.027(4) 0.018(3) 0.001(3) 0.001(3) -0.003(3) C17 0.024(3) 0.018(3) 0.016(3) 0.001(3) 0.007(3) -0.001(3) C18 0.019(3) 0.021(3) 0.018(3) 0.001(3) 0.002(3) -0.005(3) C19 0.020(3) 0.020(4) 0.021(3) 0.000(3) 0.007(3) -0.001(3) C20 0.020(3) 0.021(3) 0.020(3) -0.001(3) 0.007(3) -0.006(3) C21 0.024(3) 0.025(4) 0.026(3) -0.005(3) 0.010(3) 0.002(3) C22 0.022(3) 0.018(3) 0.028(3) 0.001(3) -0.001(3) 0.010(3) C23 0.028(3) 0.020(3) 0.018(3) 0.000(3) 0.003(3) -0.004(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' 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 _geom_angle_publ_flag C5 O1 C1 114.1(5) . . ? C11 N1 C3 116.9(5) . . ? O1 C1 C8 108.4(5) . . ? O1 C1 C9 106.5(5) . . ? C8 C1 C9 107.3(6) . . ? O1 C1 C2 108.3(5) . . ? C8 C1 C2 113.0(5) . . ? C9 C1 C2 113.0(5) . . ? C1 C2 C7 109.5(5) . . ? C1 C2 C3 108.4(5) . . ? C7 C2 C3 108.2(5) . . ? C1 C2 H2 110.2 . . ? C7 C2 H2 110.2 . . ? C3 C2 H2 110.2 . . ? N1 C3 C4 110.5(6) . . ? N1 C3 C2 109.3(5) . . ? C4 C3 C2 108.0(5) . . ? N1 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? C5 C4 C3 110.0(5) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? O1 C5 C10 105.4(5) . . ? O1 C5 C4 108.4(6) . . ? C10 C5 C4 113.1(5) . . ? O1 C5 C6 108.6(5) . . ? C10 C5 C6 111.8(6) . . ? C4 C5 C6 109.3(5) . . ? C5 C6 C7 109.6(5) . . ? C5 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C2 C7 C6 107.8(5) . . ? C2 C7 H7A 110.1 . . ? C6 C7 H7A 110.1 . . ? C2 C7 H7B 110.1 . . ? C6 C7 H7B 110.1 . . ? H7A C7 H7B 108.5 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C18 125.0(6) . . ? N1 C11 C12 117.3(6) . . ? C18 C11 C12 117.7(5) . . ? C17 C12 C13 118.4(6) . . ? C17 C12 C11 120.5(6) . . ? C13 C12 C11 121.0(5) . . ? C14 C13 C12 120.6(6) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.7(7) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.0(6) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 119.9(6) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C12 C17 C16 121.3(6) . . ? C12 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C23 119.0(6) . . ? C19 C18 C11 119.7(6) . . ? C23 C18 C11 121.3(6) . . ? C20 C19 C18 119.7(6) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C21 C20 C19 121.0(6) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 119.5(6) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 120.8(6) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C18 120.0(6) . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.452(8) . ? O1 C1 1.459(7) . ? N1 C11 1.299(8) . ? N1 C3 1.471(8) . ? C1 C8 1.530(9) . ? C1 C9 1.530(10) . ? C1 C2 1.538(9) . ? C2 C7 1.546(9) . ? C2 C3 1.546(9) . ? C2 H2 1.0000 . ? C3 C4 1.543(8) . ? C3 H3 1.0000 . ? C4 C5 1.518(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.514(9) . ? C5 C6 1.520(9) . ? C6 C7 1.551(9) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C18 1.484(9) . ? C11 C12 1.491(9) . ? C12 C17 1.387(8) . ? C12 C13 1.393(9) . ? C13 C14 1.383(9) . ? C13 H13 0.9500 . ? C14 C15 1.397(9) . ? C14 H14 0.9500 . ? C15 C16 1.383(10) . ? C15 H15 0.9500 . ? C16 C17 1.395(9) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.401(8) . ? C18 C23 1.406(9) . ? C19 C20 1.388(8) . ? C19 H19 0.9500 . ? C20 C21 1.386(9) . ? C20 H20 0.9500 . ? C21 C22 1.377(9) . ? C21 H21 0.9500 . ? C22 C23 1.390(9) . ? C22 H22 0.9500 . ? C23 H23 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C1 C8 -111.5(6) . . . . ? C5 O1 C1 C9 133.3(5) . . . . ? C5 O1 C1 C2 11.5(7) . . . . ? O1 C1 C2 C7 -65.0(7) . . . . ? C8 C1 C2 C7 55.1(7) . . . . ? C9 C1 C2 C7 177.3(5) . . . . ? O1 C1 C2 C3 52.9(7) . . . . ? C8 C1 C2 C3 173.0(5) . . . . ? C9 C1 C2 C3 -64.8(7) . . . . ? C11 N1 C3 C4 89.7(6) . . . . ? C11 N1 C3 C2 -151.5(6) . . . . ? C1 C2 C3 N1 175.6(5) . . . . ? C7 C2 C3 N1 -65.7(6) . . . . ? C1 C2 C3 C4 -64.1(7) . . . . ? C7 C2 C3 C4 54.6(7) . . . . ? N1 C3 C4 C5 130.2(6) . . . . ? C2 C3 C4 C5 10.7(8) . . . . ? C1 O1 C5 C10 172.3(5) . . . . ? C1 O1 C5 C4 -66.4(6) . . . . ? C1 O1 C5 C6 52.3(7) . . . . ? C3 C4 C5 O1 51.5(7) . . . . ? C3 C4 C5 C10 168.0(6) . . . . ? C3 C4 C5 C6 -66.7(7) . . . . ? O1 C5 C6 C7 -65.8(7) . . . . ? C10 C5 C6 C7 178.4(6) . . . . ? C4 C5 C6 C7 52.4(7) . . . . ? C1 C2 C7 C6 49.5(7) . . . . ? C3 C2 C7 C6 -68.4(6) . . . . ? C5 C6 C7 C2 12.8(7) . . . . ? C3 N1 C11 C18 -1.8(9) . . . . ? C3 N1 C11 C12 -179.2(5) . . . . ? N1 C11 C12 C17 -162.3(6) . . . . ? C18 C11 C12 C17 20.1(9) . . . . ? N1 C11 C12 C13 17.7(9) . . . . ? C18 C11 C12 C13 -159.8(6) . . . . ? C17 C12 C13 C14 0.7(9) . . . . ? C11 C12 C13 C14 -179.3(6) . . . . ? C12 C13 C14 C15 0.5(10) . . . . ? C13 C14 C15 C16 -0.6(10) . . . . ? C14 C15 C16 C17 -0.4(10) . . . . ? C13 C12 C17 C16 -1.8(10) . . . . ? C11 C12 C17 C16 178.2(6) . . . . ? C15 C16 C17 C12 1.7(10) . . . . ? N1 C11 C18 C19 -85.4(8) . . . . ? C12 C11 C18 C19 91.9(7) . . . . ? N1 C11 C18 C23 94.0(8) . . . . ? C12 C11 C18 C23 -88.7(8) . . . . ? C23 C18 C19 C20 0.6(9) . . . . ? C11 C18 C19 C20 180.0(6) . . . . ? C18 C19 C20 C21 -0.1(9) . . . . ? C19 C20 C21 C22 -0.3(10) . . . . ? C20 C21 C22 C23 0.2(10) . . . . ? C21 C22 C23 C18 0.3(10) . . . . ? C19 C18 C23 C22 -0.7(10) . . . . ? C11 C18 C23 C22 179.9(6) . . . . ?