#------------------------------------------------------------------------------ #$Date: 2016-07-01 13:49:42 +0300 (Fri, 01 Jul 2016) $ #$Revision: 184112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119078.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_7119078 loop_ _publ_author_name 'Rong-Guo Shi' 'Xiao-Hua Wang' 'Ruzhang Liu' 'Chao-Guo Yan' _publ_section_title ; Two-carbon ring expansion of isatin: a convenient construction of a dibenzo[b,d]azepinone scaffold ; _journal_name_full Chem.Commun. _journal_page_first 6280 _journal_volume 52 _journal_year 2016 _chemical_formula_sum 'C30 H21 N3 O5' _chemical_formula_weight 503.50 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_block_doi 10.5517/cc1kkq1w _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-01-13 deposited with the CCDC. 2016-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 112.1542(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.8577(7) _cell_length_b 14.7678(8) _cell_length_c 16.2529(8) _cell_measurement_reflns_used 4375 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.04 _cell_measurement_theta_min 2.22 _cell_volume 2858.3(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_unetI/netI 0.0559 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 20467 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.020 _diffrn_reflns_theta_max 25.020 _diffrn_reflns_theta_min 2.197 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_density_diffrn 1.170 _exptl_crystal_description block _exptl_crystal_F_000 1048 _exptl_crystal_size_max 0.080 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.187 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 344 _refine_ls_number_reflns 5048 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0659 _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^)+(0.0804P)^2^+1.6407P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1613 _refine_ls_wR_factor_ref 0.1825 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3174 _reflns_number_total 5048 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6cc00525j2.cif _cod_data_source_block 3b _cod_database_code 7119078 _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_estimated_absorpt_t_min 0.994 _shelx_estimated_absorpt_t_max 0.996 _platon_squeeze_void_probe_radius 1.20 _shelx_res_file ; 20151126yzu2_0m_sqd.res created by SHELXL-2014/7 TITL 20151126yzu2_0m in P2(1)/c CELL 0.71073 12.85770 14.76780 16.25290 90.0000 112.1542 90.0000 ZERR 4.00 0.00070 0.00080 0.00080 0.0000 0.0018 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 120 84 12 20 OMIT -3.00 50.05 L.S. 8 ACTA BOND $h FMAP 2 PLAN 20 HTAB N1 O2_$3 EQIV $3 x, -y+3/2, z+1/2 HTAB C13 O1_$2 EQIV $2 x, -y+3/2, z-1/2 HTAB C11 O5_$1 EQIV $1 -x+1, y-1/2, -z+1/2 HTAB C10 O3 size .08 .07 .05 htab conf TEMP 23.000 WGHT 0.080400 1.640700 FVAR 1.20383 MOLE 1 C1 1 0.368468 0.519016 0.083489 11.00000 0.04227 0.04208 = 0.03482 -0.00163 0.01419 -0.00590 C2 1 0.403940 0.431400 0.102118 11.00000 0.05782 0.04168 = 0.04795 0.00330 0.01353 -0.00242 AFIX 43 H2 2 0.423190 0.407815 0.159008 11.00000 -1.20000 AFIX 0 C3 1 0.410282 0.378892 0.033530 11.00000 0.05945 0.04217 = 0.06817 -0.01110 0.02166 0.00116 AFIX 43 H3 2 0.435043 0.319316 0.044760 11.00000 -1.20000 AFIX 0 C4 1 0.380619 0.413309 -0.050830 11.00000 0.06135 0.05005 = 0.06014 -0.02004 0.02929 -0.00374 AFIX 43 H4 2 0.385526 0.376745 -0.095815 11.00000 -1.20000 AFIX 0 C5 1 0.343312 0.502258 -0.069752 11.00000 0.05463 0.05266 = 0.04322 -0.01160 0.02388 -0.00481 AFIX 43 H5 2 0.322220 0.525504 -0.126929 11.00000 -1.20000 AFIX 0 C6 1 0.338623 0.554525 -0.001511 11.00000 0.03711 0.04674 = 0.03500 -0.00775 0.01602 -0.00473 C7 1 0.322752 0.672514 0.090238 11.00000 0.04375 0.03776 = 0.02529 -0.00254 0.01423 -0.00659 C8 1 0.287993 0.758454 0.123396 11.00000 0.04200 0.04370 = 0.02395 -0.00180 0.01451 -0.00319 C9 1 0.292662 0.843250 0.067235 11.00000 0.03981 0.04388 = 0.02440 -0.00075 0.01301 -0.00230 AFIX 13 H9 2 0.228227 0.837090 0.010925 11.00000 -1.20000 AFIX 0 C10 1 0.496862 0.828963 0.099039 11.00000 0.05433 0.04870 = 0.03547 0.00541 0.02198 0.00654 AFIX 43 H10 2 0.507780 0.806229 0.155055 11.00000 -1.20000 AFIX 0 C11 1 0.587798 0.841199 0.074040 11.00000 0.05539 0.05952 = 0.05245 0.01300 0.02656 0.00971 AFIX 43 H11 2 0.660209 0.828805 0.113876 11.00000 -1.20000 AFIX 0 C12 1 0.570138 0.871735 -0.009926 11.00000 0.07056 0.05448 = 0.06169 0.00540 0.04502 0.00463 AFIX 43 H12 2 0.630477 0.879624 -0.027537 11.00000 -1.20000 AFIX 0 C13 1 0.462986 0.890556 -0.067729 11.00000 0.07549 0.05263 = 0.03847 0.00571 0.03315 -0.00416 AFIX 43 H13 2 0.449788 0.910640 -0.125030 11.00000 -1.20000 AFIX 0 C14 1 0.376159 0.879395 -0.039959 11.00000 0.05549 0.05229 = 0.02653 0.00291 0.01429 -0.00394 AFIX 43 H14 2 0.303455 0.892448 -0.078849 11.00000 -1.20000 AFIX 0 C15 1 0.275474 0.933223 0.106313 11.00000 0.04307 0.04263 = 0.02871 0.00531 0.01507 0.00145 C16 1 0.361932 0.982952 0.165972 11.00000 0.04192 0.04562 = 0.03796 -0.00148 0.01684 0.00180 AFIX 43 H16 2 0.434966 0.960932 0.184540 11.00000 -1.20000 AFIX 0 C17 1 0.342234 1.065192 0.198892 11.00000 0.05652 0.04954 = 0.04033 -0.00578 0.02109 -0.00215 AFIX 43 H17 2 0.400991 1.099144 0.238078 11.00000 -1.20000 AFIX 0 C18 1 0.234403 1.094414 0.172006 11.00000 0.06458 0.04760 = 0.03679 -0.00219 0.02416 0.00877 C19 1 0.147004 1.047262 0.113975 11.00000 0.05282 0.06495 = 0.07696 -0.01079 0.01699 0.01729 AFIX 43 H19 2 0.073956 1.068864 0.097115 11.00000 -1.20000 AFIX 0 C20 1 0.168219 0.967147 0.080578 11.00000 0.04498 0.06643 = 0.06793 -0.01975 0.00323 0.00716 AFIX 43 H20 2 0.108902 0.935098 0.039704 11.00000 -1.20000 AFIX 0 C21 1 0.355604 0.772914 0.225198 11.00000 0.05918 0.03690 = 0.02662 -0.00078 0.01766 -0.00504 C22 1 0.170697 0.764703 0.205752 11.00000 0.05777 0.06129 = 0.04185 0.00266 0.03043 -0.00012 C23 1 0.168726 0.752519 0.120947 11.00000 0.04906 0.04786 = 0.03779 0.00123 0.02440 -0.00609 C24 1 0.069076 0.734488 0.051699 11.00000 0.05703 0.06557 = 0.04614 0.00066 0.02537 -0.01125 AFIX 43 H24 2 0.068066 0.725336 -0.005210 11.00000 -1.20000 AFIX 0 C25 1 -0.030306 0.729973 0.067024 11.00000 0.05305 0.10183 = 0.06564 0.01790 0.02519 -0.00635 C26 1 -0.025122 0.743828 0.152646 11.00000 0.06045 0.13895 = 0.08218 0.01934 0.04506 -0.00588 AFIX 43 H26 2 -0.091351 0.741194 0.163115 11.00000 -1.20000 AFIX 0 C27 1 0.074255 0.761436 0.223427 11.00000 0.08155 0.11505 = 0.06004 0.01056 0.05016 0.00675 AFIX 43 H27 2 0.075754 0.770659 0.280467 11.00000 -1.20000 AFIX 0 C28 1 -0.140898 0.708013 -0.005753 11.00000 0.05275 0.16672 = 0.09449 0.02077 0.01955 -0.01738 AFIX 137 H28A 2 -0.172710 0.655402 0.010453 11.00000 -1.50000 H28B 2 -0.129450 0.696277 -0.059825 11.00000 -1.50000 H28C 2 -0.191191 0.758331 -0.014385 11.00000 -1.50000 AFIX 0 C29 1 0.305070 0.651767 0.000698 11.00000 0.04555 0.04044 = 0.02851 -0.00161 0.01803 -0.00593 C30 1 0.356327 0.592785 0.142174 11.00000 0.03945 0.04543 = 0.03098 -0.00178 0.01280 -0.00784 N1 3 0.280139 0.780205 0.264765 11.00000 0.06609 0.06319 = 0.02517 -0.00530 0.02492 -0.00373 AFIX 3 H1A 2 0.301028 0.786267 0.325587 11.00000 -1.20000 AFIX 0 N2 3 0.393238 0.849969 0.042303 11.00000 0.04802 0.03553 = 0.02923 -0.00086 0.01832 -0.00130 N3 3 0.210081 1.181495 0.206360 11.00000 0.08939 0.06074 = 0.05471 -0.00071 0.03403 0.01656 O1 4 0.373276 0.582050 0.222498 11.00000 0.08353 0.05085 = 0.02768 0.00305 0.01768 -0.00512 O2 4 0.269129 0.701802 -0.066760 11.00000 0.07317 0.05069 = 0.02481 0.00132 0.01969 0.00008 O3 4 0.457112 0.779480 0.262039 11.00000 0.05399 0.06122 = 0.02951 -0.00367 0.01095 -0.01384 O4 4 0.112772 1.204710 0.184841 11.00000 0.10044 0.09341 = 0.12769 -0.01056 0.07001 0.02988 O5 4 0.288703 1.226355 0.252895 11.00000 0.11385 0.07792 = 0.09030 -0.03999 0.00996 0.01478 HKLF 4 REM 20151126yzu2_0m in P2(1)/c REM R1 = 0.0659 for 3174 Fo > 4sig(Fo) and 0.1104 for all 5048 data REM 344 parameters refined using 0 restraints END WGHT 0.0792 1.6831 REM Instructions for potential hydrogen bonds HTAB C10 O3 HTAB C11 O5_$1 HTAB C13 O1_$2 HTAB N1 O2_$3 REM Highest difference peak 0.187, deepest hole -0.210, 1-sigma level 0.048 Q1 1 0.4147 0.5253 0.2536 11.00000 0.05 0.19 Q2 1 0.4849 0.8527 0.3009 11.00000 0.05 0.18 Q3 1 -0.1262 0.5414 -0.1814 11.00000 0.05 0.17 Q4 1 0.3429 0.5622 0.2741 11.00000 0.05 0.17 Q5 1 -0.0157 1.0197 0.2192 11.00000 0.05 0.16 Q6 1 0.5094 0.4616 -0.0283 11.00000 0.05 0.16 Q7 1 0.0816 0.9679 -0.2257 11.00000 0.05 0.15 Q8 1 -0.1982 0.8062 0.1190 11.00000 0.05 0.15 Q9 1 0.2574 0.5426 0.2817 11.00000 0.05 0.15 Q10 1 0.5203 0.7843 0.2370 11.00000 0.05 0.15 Q11 1 0.3017 0.7546 -0.0930 11.00000 0.05 0.15 Q12 1 0.0580 1.1412 0.1731 11.00000 0.05 0.14 Q13 1 0.3959 0.9598 -0.1311 11.00000 0.05 0.14 Q14 1 0.3445 0.6813 -0.0803 11.00000 0.05 0.14 Q15 1 0.3431 1.0013 0.2256 11.00000 0.05 0.14 Q16 1 0.0920 0.9006 0.0691 11.00000 0.05 0.14 Q17 1 -0.0656 0.5789 -0.1268 11.00000 0.05 0.14 Q18 1 0.3959 1.1397 0.1945 11.00000 0.05 0.14 Q19 1 -0.2007 0.6990 0.0134 11.00000 0.05 0.14 Q20 1 -0.1030 0.8037 0.1698 11.00000 0.05 0.14 ; _shelx_res_checksum 15695 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 C1 C 0.3685(3) 0.5190(2) 0.08349(19) 0.0398(7) Uani 1 1 d . . . . . C2 C 0.4039(3) 0.4314(2) 0.1021(2) 0.0510(9) Uani 1 1 d . . . . . H2 H 0.4232 0.4078 0.1590 0.061 Uiso 1 1 calc R U . . . C3 C 0.4103(3) 0.3789(2) 0.0335(2) 0.0573(9) Uani 1 1 d . . . . . H3 H 0.4350 0.3193 0.0448 0.069 Uiso 1 1 calc R U . . . C4 C 0.3806(3) 0.4133(2) -0.0508(2) 0.0553(9) Uani 1 1 d . . . . . H4 H 0.3855 0.3767 -0.0958 0.066 Uiso 1 1 calc R U . . . C5 C 0.3433(3) 0.5023(2) -0.0698(2) 0.0486(8) Uani 1 1 d . . . . . H5 H 0.3222 0.5255 -0.1269 0.058 Uiso 1 1 calc R U . . . C6 C 0.3386(2) 0.5545(2) -0.00151(19) 0.0389(7) Uani 1 1 d . . . . . C7 C 0.3228(2) 0.67251(19) 0.09024(17) 0.0352(7) Uani 1 1 d . . . . . C8 C 0.2880(2) 0.7585(2) 0.12340(17) 0.0359(7) Uani 1 1 d . . . . . C9 C 0.2927(2) 0.84325(19) 0.06723(18) 0.0358(7) Uani 1 1 d . . . . . H9 H 0.2282 0.8371 0.0109 0.043 Uiso 1 1 calc R U . . . C10 C 0.4969(3) 0.8290(2) 0.0990(2) 0.0447(8) Uani 1 1 d . . . . . H10 H 0.5078 0.8062 0.1551 0.054 Uiso 1 1 calc R U . . . C11 C 0.5878(3) 0.8412(2) 0.0740(2) 0.0540(9) Uani 1 1 d . . . . . H11 H 0.6602 0.8288 0.1139 0.065 Uiso 1 1 calc R U . . . C12 C 0.5701(3) 0.8717(2) -0.0099(2) 0.0564(9) Uani 1 1 d . . . . . H12 H 0.6305 0.8796 -0.0275 0.068 Uiso 1 1 calc R U . . . C13 C 0.4630(3) 0.8906(2) -0.0677(2) 0.0521(9) Uani 1 1 d . . . . . H13 H 0.4498 0.9106 -0.1250 0.063 Uiso 1 1 calc R U . . . C14 C 0.3762(3) 0.8794(2) -0.03996(19) 0.0451(8) Uani 1 1 d . . . . . H14 H 0.3035 0.8924 -0.0788 0.054 Uiso 1 1 calc R U . . . C15 C 0.2755(2) 0.9332(2) 0.10631(18) 0.0377(7) Uani 1 1 d . . . . . C16 C 0.3619(3) 0.9830(2) 0.16597(19) 0.0413(8) Uani 1 1 d . . . . . H16 H 0.4350 0.9609 0.1845 0.050 Uiso 1 1 calc R U . . . C17 C 0.3422(3) 1.0652(2) 0.1989(2) 0.0480(8) Uani 1 1 d . . . . . H17 H 0.4010 1.0991 0.2381 0.058 Uiso 1 1 calc R U . . . C18 C 0.2344(3) 1.0944(2) 0.1720(2) 0.0482(8) Uani 1 1 d . . . . . C19 C 0.1470(3) 1.0473(3) 0.1140(3) 0.0671(11) Uani 1 1 d . . . . . H19 H 0.0740 1.0689 0.0971 0.081 Uiso 1 1 calc R U . . . C20 C 0.1682(3) 0.9671(3) 0.0806(3) 0.0651(11) Uani 1 1 d . . . . . H20 H 0.1089 0.9351 0.0397 0.078 Uiso 1 1 calc R U . . . C21 C 0.3556(3) 0.77291(19) 0.22520(19) 0.0405(7) Uani 1 1 d . . . . . C22 C 0.1707(3) 0.7647(2) 0.2058(2) 0.0502(9) Uani 1 1 d . . . . . C23 C 0.1687(3) 0.7525(2) 0.1209(2) 0.0426(8) Uani 1 1 d . . . . . C24 C 0.0691(3) 0.7345(2) 0.0517(2) 0.0545(9) Uani 1 1 d . . . . . H24 H 0.0681 0.7253 -0.0052 0.065 Uiso 1 1 calc R U . . . C25 C -0.0303(3) 0.7300(3) 0.0670(3) 0.0727(12) Uani 1 1 d . . . . . C26 C -0.0251(4) 0.7438(4) 0.1526(3) 0.0885(14) Uani 1 1 d . . . . . H26 H -0.0914 0.7412 0.1631 0.106 Uiso 1 1 calc R U . . . C27 C 0.0743(4) 0.7614(3) 0.2234(3) 0.0787(13) Uani 1 1 d . . . . . H27 H 0.0758 0.7707 0.2805 0.094 Uiso 1 1 calc R U . . . C28 C -0.1409(3) 0.7080(4) -0.0058(3) 0.1071(18) Uani 1 1 d . . . . . H28A H -0.1727 0.6554 0.0105 0.161 Uiso 1 1 calc R U . . . H28B H -0.1294 0.6963 -0.0598 0.161 Uiso 1 1 calc R U . . . H28C H -0.1912 0.7583 -0.0144 0.161 Uiso 1 1 calc R U . . . C29 C 0.3051(2) 0.6518(2) 0.00070(18) 0.0370(7) Uani 1 1 d . . . . . C30 C 0.3563(2) 0.5928(2) 0.14217(19) 0.0388(7) Uani 1 1 d . . . . . N1 N 0.2801(2) 0.78021(18) 0.26476(16) 0.0492(7) Uani 1 1 d . . . . . H1A H 0.3010 0.7863 0.3256 0.059 Uiso 1 1 d R U . . . N2 N 0.3932(2) 0.84997(15) 0.04230(15) 0.0365(6) Uani 1 1 d . . . . . N3 N 0.2101(3) 1.1815(2) 0.2064(2) 0.0663(9) Uani 1 1 d . . . . . O1 O 0.3733(2) 0.58205(14) 0.22250(13) 0.0550(6) Uani 1 1 d . . . . . O2 O 0.26913(19) 0.70180(14) -0.06676(13) 0.0492(6) Uani 1 1 d . . . . . O3 O 0.45711(19) 0.77948(15) 0.26204(13) 0.0496(6) Uani 1 1 d . . . . . O4 O 0.1128(3) 1.2047(2) 0.1848(2) 0.0993(11) Uani 1 1 d . . . . . O5 O 0.2887(3) 1.2264(2) 0.2529(2) 0.1024(11) Uani 1 1 d . . . . . 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 C1 0.0423(18) 0.0421(18) 0.0348(17) -0.0016(14) 0.0142(14) -0.0059(15) C2 0.058(2) 0.0417(19) 0.048(2) 0.0033(16) 0.0135(17) -0.0024(16) C3 0.059(2) 0.0422(19) 0.068(3) -0.0111(18) 0.0217(19) 0.0012(17) C4 0.061(2) 0.050(2) 0.060(2) -0.0200(18) 0.0293(19) -0.0037(18) C5 0.055(2) 0.053(2) 0.0432(19) -0.0116(16) 0.0239(16) -0.0048(17) C6 0.0371(17) 0.0467(18) 0.0350(17) -0.0077(14) 0.0160(14) -0.0047(14) C7 0.0438(17) 0.0378(16) 0.0253(15) -0.0025(12) 0.0142(13) -0.0066(14) C8 0.0420(17) 0.0437(17) 0.0240(15) -0.0018(13) 0.0145(13) -0.0032(14) C9 0.0398(17) 0.0439(17) 0.0244(15) -0.0008(13) 0.0130(13) -0.0023(14) C10 0.054(2) 0.0487(19) 0.0355(17) 0.0054(14) 0.0220(16) 0.0065(16) C11 0.055(2) 0.060(2) 0.052(2) 0.0130(17) 0.0266(18) 0.0097(18) C12 0.071(3) 0.054(2) 0.062(2) 0.0054(18) 0.045(2) 0.0046(19) C13 0.075(3) 0.053(2) 0.0385(19) 0.0057(16) 0.0332(19) -0.0042(18) C14 0.055(2) 0.052(2) 0.0265(17) 0.0029(14) 0.0143(15) -0.0039(16) C15 0.0431(18) 0.0426(17) 0.0287(16) 0.0053(13) 0.0151(14) 0.0014(15) C16 0.0419(18) 0.0456(19) 0.0380(17) -0.0015(14) 0.0168(15) 0.0018(15) C17 0.057(2) 0.050(2) 0.0403(18) -0.0058(15) 0.0211(16) -0.0022(17) C18 0.065(2) 0.048(2) 0.0368(18) -0.0022(15) 0.0242(17) 0.0088(18) C19 0.053(2) 0.065(2) 0.077(3) -0.011(2) 0.017(2) 0.017(2) C20 0.045(2) 0.066(2) 0.068(2) -0.020(2) 0.0032(18) 0.0072(19) C21 0.059(2) 0.0369(17) 0.0266(16) -0.0008(13) 0.0177(16) -0.0050(16) C22 0.058(2) 0.061(2) 0.0418(19) 0.0027(16) 0.0304(17) -0.0001(18) C23 0.0491(19) 0.0479(18) 0.0378(18) 0.0012(14) 0.0244(15) -0.0061(16) C24 0.057(2) 0.066(2) 0.046(2) 0.0007(17) 0.0254(18) -0.0113(18) C25 0.053(2) 0.102(3) 0.066(3) 0.018(2) 0.025(2) -0.006(2) C26 0.060(3) 0.139(4) 0.082(3) 0.019(3) 0.045(3) -0.006(3) C27 0.082(3) 0.115(4) 0.060(3) 0.011(2) 0.050(2) 0.007(3) C28 0.053(3) 0.167(5) 0.094(4) 0.021(3) 0.020(2) -0.017(3) C29 0.0456(18) 0.0404(17) 0.0285(16) -0.0016(13) 0.0180(14) -0.0059(14) C30 0.0395(18) 0.0454(18) 0.0310(17) -0.0018(14) 0.0128(14) -0.0078(14) N1 0.0661(19) 0.0632(18) 0.0252(13) -0.0053(12) 0.0249(14) -0.0037(15) N2 0.0480(16) 0.0355(14) 0.0292(13) -0.0009(11) 0.0183(12) -0.0013(12) N3 0.089(3) 0.061(2) 0.055(2) -0.0007(17) 0.034(2) 0.017(2) O1 0.0835(18) 0.0509(13) 0.0277(12) 0.0030(10) 0.0177(11) -0.0051(12) O2 0.0732(16) 0.0507(13) 0.0248(11) 0.0013(10) 0.0197(10) 0.0001(11) O3 0.0540(15) 0.0612(15) 0.0295(11) -0.0037(10) 0.0109(11) -0.0138(12) O4 0.100(3) 0.093(2) 0.128(3) -0.0106(19) 0.070(2) 0.0299(19) O5 0.114(3) 0.078(2) 0.090(2) -0.0400(18) 0.010(2) 0.0148(19) 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 C2 C1 C6 121.4(3) . . C2 C1 C30 130.9(3) . . C6 C1 C30 107.7(3) . . C1 C2 C3 117.9(3) . . C1 C2 H2 121.1 . . C3 C2 H2 121.1 . . C4 C3 C2 121.2(3) . . C4 C3 H3 119.4 . . C2 C3 H3 119.4 . . C3 C4 C5 120.8(3) . . C3 C4 H4 119.6 . . C5 C4 H4 119.6 . . C6 C5 C4 118.0(3) . . C6 C5 H5 121.0 . . C4 C5 H5 121.0 . . C5 C6 C1 120.8(3) . . C5 C6 C29 131.1(3) . . C1 C6 C29 108.1(2) . . C30 C7 C29 109.0(2) . . C30 C7 C8 123.4(2) . . C29 C7 C8 126.3(3) . . C7 C8 C23 111.9(2) . . C7 C8 C9 112.5(2) . . C23 C8 C9 106.9(2) . . C7 C8 C21 111.7(2) . . C23 C8 C21 100.8(2) . . C9 C8 C21 112.3(2) . . N2 C9 C15 109.3(2) . . N2 C9 C8 116.0(2) . . C15 C9 C8 114.3(2) . . N2 C9 H9 105.4 . . C15 C9 H9 105.4 . . C8 C9 H9 105.4 . . N2 C10 C11 119.8(3) . . N2 C10 H10 120.1 . . C11 C10 H10 120.1 . . C12 C11 C10 119.5(3) . . C12 C11 H11 120.2 . . C10 C11 H11 120.2 . . C13 C12 C11 119.6(3) . . C13 C12 H12 120.2 . . C11 C12 H12 120.2 . . C14 C13 C12 119.0(3) . . C14 C13 H13 120.5 . . C12 C13 H13 120.5 . . N2 C14 C13 121.5(3) . . N2 C14 H14 119.3 . . C13 C14 H14 119.3 . . C20 C15 C16 118.0(3) . . C20 C15 C9 118.5(3) . . C16 C15 C9 123.5(3) . . C15 C16 C17 121.4(3) . . C15 C16 H16 119.3 . . C17 C16 H16 119.3 . . C18 C17 C16 117.8(3) . . C18 C17 H17 121.1 . . C16 C17 H17 121.1 . . C19 C18 C17 122.6(3) . . C19 C18 N3 118.1(3) . . C17 C18 N3 119.3(3) . . C18 C19 C20 118.8(3) . . C18 C19 H19 120.6 . . C20 C19 H19 120.6 . . C19 C20 C15 121.3(3) . . C19 C20 H20 119.3 . . C15 C20 H20 119.3 . . O3 C21 N1 125.9(3) . . O3 C21 C8 126.5(3) . . N1 C21 C8 107.5(3) . . C27 C22 C23 121.7(3) . . C27 C22 N1 128.3(3) . . C23 C22 N1 110.0(3) . . C24 C23 C22 120.2(3) . . C24 C23 C8 130.6(3) . . C22 C23 C8 109.1(3) . . C23 C24 C25 119.8(3) . . C23 C24 H24 120.1 . . C25 C24 H24 120.1 . . C26 C25 C24 118.3(4) . . C26 C25 C28 119.8(4) . . C24 C25 C28 122.0(4) . . C25 C26 C27 122.9(4) . . C25 C26 H26 118.5 . . C27 C26 H26 118.5 . . C22 C27 C26 117.1(4) . . C22 C27 H27 121.4 . . C26 C27 H27 121.4 . . C25 C28 H28A 109.5 . . C25 C28 H28B 109.5 . . H28A C28 H28B 109.5 . . C25 C28 H28C 109.5 . . H28A C28 H28C 109.5 . . H28B C28 H28C 109.5 . . O2 C29 C7 129.2(3) . . O2 C29 C6 123.7(2) . . C7 C29 C6 107.1(2) . . O1 C30 C7 128.4(3) . . O1 C30 C1 123.7(3) . . C7 C30 C1 107.9(2) . . C21 N1 C22 112.3(3) . . C21 N1 H1A 122.9 . . C22 N1 H1A 124.3 . . C10 N2 C14 120.5(3) . . C10 N2 C9 122.3(2) . . C14 N2 C9 117.2(3) . . O5 N3 O4 123.6(4) . . O5 N3 C18 117.8(4) . . O4 N3 C18 118.5(4) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.367(4) . C1 C6 1.390(4) . C1 C30 1.494(4) . C2 C3 1.385(5) . C2 H2 0.9300 . C3 C4 1.375(5) . C3 H3 0.9300 . C4 C5 1.392(5) . C4 H4 0.9300 . C5 C6 1.371(4) . C5 H5 0.9300 . C6 C29 1.504(4) . C7 C30 1.418(4) . C7 C29 1.419(4) . C7 C8 1.511(4) . C8 C23 1.521(4) . C8 C9 1.564(4) . C8 C21 1.567(4) . C9 N2 1.497(4) . C9 C15 1.524(4) . C9 H9 0.9800 . C10 N2 1.340(4) . C10 C11 1.387(4) . C10 H10 0.9300 . C11 C12 1.372(5) . C11 H11 0.9300 . C12 C13 1.372(5) . C12 H12 0.9300 . C13 C14 1.363(4) . C13 H13 0.9300 . C14 N2 1.343(4) . C14 H14 0.9300 . C15 C20 1.376(4) . C15 C16 1.379(4) . C16 C17 1.388(4) . C16 H16 0.9300 . C17 C18 1.357(5) . C17 H17 0.9300 . C18 C19 1.356(5) . C18 N3 1.482(4) . C19 C20 1.371(5) . C19 H19 0.9300 . C20 H20 0.9300 . C21 O3 1.217(4) . C21 N1 1.355(4) . C22 C27 1.375(5) . C22 C23 1.381(4) . C22 N1 1.391(4) . C23 C24 1.375(4) . C24 C25 1.393(5) . C24 H24 0.9300 . C25 C26 1.383(6) . C25 C28 1.503(6) . C26 C27 1.384(6) . C26 H26 0.9300 . C27 H27 0.9300 . C28 H28A 0.9600 . C28 H28B 0.9600 . C28 H28C 0.9600 . C29 O2 1.257(3) . C30 O1 1.250(3) . N1 H1A 0.9258 . N3 O5 1.207(4) . N3 O4 1.215(4) . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2 0.93 1.95 2.807(3) 153.2 4_576 C13 H13 O1 0.93 2.30 3.186(4) 159.6 4_575 C11 H11 O5 0.93 2.52 3.153(5) 125.8 2_645 C10 H10 O3 0.93 2.11 2.972(4) 153.4 . 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 C6 C1 C2 C3 0.6(5) . . . . C30 C1 C2 C3 -177.7(3) . . . . C1 C2 C3 C4 -0.8(5) . . . . C2 C3 C4 C5 0.0(5) . . . . C3 C4 C5 C6 0.9(5) . . . . C4 C5 C6 C1 -1.1(5) . . . . C4 C5 C6 C29 178.6(3) . . . . C2 C1 C6 C5 0.4(5) . . . . C30 C1 C6 C5 179.0(3) . . . . C2 C1 C6 C29 -179.4(3) . . . . C30 C1 C6 C29 -0.8(3) . . . . C30 C7 C8 C23 -78.1(3) . . . . C29 C7 C8 C23 87.7(3) . . . . C30 C7 C8 C9 161.5(3) . . . . C29 C7 C8 C9 -32.7(4) . . . . C30 C7 C8 C21 34.1(4) . . . . C29 C7 C8 C21 -160.1(3) . . . . C7 C8 C9 N2 -42.7(3) . . . . C23 C8 C9 N2 -165.9(2) . . . . C21 C8 C9 N2 84.4(3) . . . . C7 C8 C9 C15 -171.3(2) . . . . C23 C8 C9 C15 65.5(3) . . . . C21 C8 C9 C15 -44.2(3) . . . . N2 C10 C11 C12 -2.3(5) . . . . C10 C11 C12 C13 0.6(5) . . . . C11 C12 C13 C14 0.7(5) . . . . C12 C13 C14 N2 -0.4(5) . . . . N2 C9 C15 C20 136.8(3) . . . . C8 C9 C15 C20 -91.3(3) . . . . N2 C9 C15 C16 -42.8(4) . . . . C8 C9 C15 C16 89.0(3) . . . . C20 C15 C16 C17 -0.5(4) . . . . C9 C15 C16 C17 179.2(3) . . . . C15 C16 C17 C18 1.5(4) . . . . C16 C17 C18 C19 -1.0(5) . . . . C16 C17 C18 N3 179.5(3) . . . . C17 C18 C19 C20 -0.4(6) . . . . N3 C18 C19 C20 179.1(3) . . . . C18 C19 C20 C15 1.5(6) . . . . C16 C15 C20 C19 -1.0(5) . . . . C9 C15 C20 C19 179.3(3) . . . . C7 C8 C21 O3 59.0(4) . . . . C23 C8 C21 O3 178.0(3) . . . . C9 C8 C21 O3 -68.5(4) . . . . C7 C8 C21 N1 -123.2(3) . . . . C23 C8 C21 N1 -4.2(3) . . . . C9 C8 C21 N1 109.3(3) . . . . C27 C22 C23 C24 -1.5(5) . . . . N1 C22 C23 C24 178.8(3) . . . . C27 C22 C23 C8 -179.1(3) . . . . N1 C22 C23 C8 1.3(4) . . . . C7 C8 C23 C24 -56.6(4) . . . . C9 C8 C23 C24 67.0(4) . . . . C21 C8 C23 C24 -175.5(3) . . . . C7 C8 C23 C22 120.6(3) . . . . C9 C8 C23 C22 -115.7(3) . . . . C21 C8 C23 C22 1.7(3) . . . . C22 C23 C24 C25 1.0(5) . . . . C8 C23 C24 C25 178.0(3) . . . . C23 C24 C25 C26 -0.1(6) . . . . C23 C24 C25 C28 -178.3(4) . . . . C24 C25 C26 C27 -0.3(7) . . . . C28 C25 C26 C27 177.9(5) . . . . C23 C22 C27 C26 1.1(6) . . . . N1 C22 C27 C26 -179.3(4) . . . . C25 C26 C27 C22 -0.1(7) . . . . C30 C7 C29 O2 175.7(3) . . . . C8 C7 C29 O2 8.2(5) . . . . C30 C7 C29 C6 -4.6(3) . . . . C8 C7 C29 C6 -172.1(3) . . . . C5 C6 C29 O2 3.3(5) . . . . C1 C6 C29 O2 -177.0(3) . . . . C5 C6 C29 C7 -176.4(3) . . . . C1 C6 C29 C7 3.3(3) . . . . C29 C7 C30 O1 -175.4(3) . . . . C8 C7 C30 O1 -7.5(5) . . . . C29 C7 C30 C1 4.2(3) . . . . C8 C7 C30 C1 172.1(3) . . . . C2 C1 C30 O1 -4.0(5) . . . . C6 C1 C30 O1 177.6(3) . . . . C2 C1 C30 C7 176.4(3) . . . . C6 C1 C30 C7 -2.0(3) . . . . O3 C21 N1 C22 -176.8(3) . . . . C8 C21 N1 C22 5.4(3) . . . . C27 C22 N1 C21 176.0(4) . . . . C23 C22 N1 C21 -4.4(4) . . . . C11 C10 N2 C14 2.7(4) . . . . C11 C10 N2 C9 -176.4(3) . . . . C13 C14 N2 C10 -1.3(4) . . . . C13 C14 N2 C9 177.8(3) . . . . C15 C9 N2 C10 90.1(3) . . . . C8 C9 N2 C10 -40.9(4) . . . . C15 C9 N2 C14 -89.1(3) . . . . C8 C9 N2 C14 140.0(3) . . . . C19 C18 N3 O5 -174.8(4) . . . . C17 C18 N3 O5 4.8(5) . . . . C19 C18 N3 O4 3.7(5) . . . . C17 C18 N3 O4 -176.7(3) . . . . loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.500 329 73 ' ' 2 0.000 0.500 0.000 329 73 ' '