#------------------------------------------------------------------------------ #$Date: 2016-11-04 05:57:05 +0200 (Fri, 04 Nov 2016) $ #$Revision: 187800 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/69/7226988.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_7226988 loop_ _publ_author_name 'Xu, Jia' 'Huang, Yuting' 'Ruan, Sida' 'Chi, Zongliang' 'Qin, Kunming' 'Cai, Baochang' 'Cai, Ting' _publ_section_title ; Cocrystals of isoliquiritigenin with enhanced pharmacokinetic performance ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C6CE01809B _journal_year 2016 _chemical_formula_sum 'C21 H18 N2 O5' _chemical_formula_weight 378.37 _chemical_name_systematic 'isoliquiritigenin-nicotinamide cocrystal' _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yac' _space_group_name_H-M_alt 'P 1 2/n 1' _symmetry_space_group_name_Hall '-P 2yac' _symmetry_space_group_name_H-M 'P 1 2/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-09-28 deposited with the CCDC. 2016-10-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 114.968(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 21.909(6) _cell_length_b 3.7898(13) _cell_length_c 23.918(7) _cell_measurement_reflns_used 2362 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.2 _cell_measurement_theta_min 2.61 _cell_volume 1800.3(10) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _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 0.0505 _diffrn_reflns_av_unetI/netI 0.0716 _diffrn_reflns_Laue_measured_fraction_full 0.967 _diffrn_reflns_Laue_measured_fraction_max 0.967 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6927 _diffrn_reflns_point_group_measured_fraction_full 0.967 _diffrn_reflns_point_group_measured_fraction_max 0.967 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.051 _exptl_absorpt_coefficient_mu 0.101 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.396 _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.220 _refine_diff_density_max 0.464 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.096 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 3086 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.193 _refine_ls_R_factor_all 0.1738 _refine_ls_R_factor_gt 0.1314 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+18.0812P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2294 _refine_ls_wR_factor_ref 0.2442 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2260 _reflns_number_total 3086 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce01809b2.cif _cod_data_source_block 20151029ykdc_0m _cod_database_code 7226988 _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 0.973 _shelx_estimated_absorpt_t_max 0.978 _shelx_res_file ; 20151029ykdc_0m.res created by SHELXL-2014/7 TITL 20151029ykdc_0m in Pn New: P2/n CELL 0.71073 21.9090 3.7898 23.9180 90.000 114.968 90.000 ZERR 4 0.0060 0.0013 0.0070 0.000 0.008 0.000 LATT 1 SYMM 0.50000 - X , Y , 0.50000 - Z SFAC C H N O UNIT 84 72 8 20 L.S. 20 OMIT 0 50 omit -21 2 9 omit -13 3 17 omit -23 2 14 omit 0 3 17 omit -17 1 24 ACTA BOND $H FMAP 2 PLAN 0 HTAB O4 O5_$4 HTAB O3 O2 HTAB O1 N2_$3 HTAB N1 O3 HTAB N1 O5_$2 HTAB C12 O1_$1 CONF HTAB SIZE .27 .24 .22 CONF WGHT 0.000000 18.081200 FVAR 0.14260 RESI 0 EQIV $1 -x+3/2, y-1, -z+1/2 HTAB C12 O1_$1 EQIV $2 -x+1/2, y, -z+1/2 HTAB N1 O5_$2 HTAB N1 O3 EQIV $3 -x+1, -y+2, -z HTAB O1 N2_$3 HTAB O3 O2 EQIV $4 -x+1/2, y-1, -z+1/2 HTAB O4 O5_$4 TEMP 23 C1 1 0.749168 1.009987 0.102552 11.00000 0.02666 0.02996 = 0.02753 0.00293 0.01681 0.00728 C2 1 0.689792 1.028449 0.049593 11.00000 0.03522 0.03271 = 0.02367 0.00433 0.01904 0.00198 AFIX 43 H2 2 0.689690 1.120882 0.013535 11.00000 -1.20000 AFIX 0 C3 1 0.630654 0.909215 0.050418 11.00000 0.01852 0.03531 = 0.03790 0.00793 0.01529 -0.00447 AFIX 43 H3 2 0.591009 0.920876 0.014482 11.00000 -1.20000 AFIX 0 C4 1 0.628855 0.771814 0.103733 11.00000 0.02326 0.02133 = 0.03447 0.00290 0.01960 0.01177 C5 1 0.689912 0.749001 0.156753 11.00000 0.03274 0.03489 = 0.03444 0.01118 0.01924 -0.00003 AFIX 43 H5 2 0.690221 0.654022 0.192724 11.00000 -1.20000 AFIX 0 C6 1 0.749901 0.865956 0.156394 11.00000 0.02186 0.05740 = 0.02750 0.01871 0.00598 0.00944 AFIX 43 H6 2 0.790062 0.848189 0.191715 11.00000 -1.20000 AFIX 0 C7 1 0.565327 0.652861 0.103026 11.00000 0.01944 0.02161 = 0.04405 -0.00258 0.02002 0.00211 AFIX 43 H7 2 0.527332 0.677967 0.065961 11.00000 -1.20000 AFIX 0 C8 1 0.555693 0.511107 0.150017 11.00000 0.02949 0.02353 = 0.03452 0.00252 0.02124 -0.00259 AFIX 43 H8 2 0.592574 0.482796 0.187810 11.00000 -1.20000 AFIX 0 C9 1 0.488857 0.398523 0.144012 11.00000 0.02775 0.02012 = 0.02837 -0.00295 0.01744 0.00632 C10 1 0.482556 0.241532 0.197754 11.00000 0.02259 0.01326 = 0.03020 -0.00200 0.01809 0.00188 C11 1 0.536431 0.199735 0.255952 11.00000 0.01572 0.02085 = 0.03574 -0.00375 0.01480 -0.00212 AFIX 43 H11 2 0.579301 0.269491 0.261463 11.00000 -1.20000 AFIX 0 C12 1 0.527759 0.058668 0.305117 11.00000 0.01729 0.02861 = 0.02906 -0.00169 0.01137 0.00452 AFIX 43 H12 2 0.564421 0.035832 0.343208 11.00000 -1.20000 AFIX 0 C13 1 0.463674 -0.050699 0.297827 11.00000 0.02579 0.01103 = 0.02200 0.00139 0.01953 -0.00124 C14 1 0.410047 -0.012363 0.241061 11.00000 0.01026 0.02490 = 0.03002 -0.00212 0.01214 0.00066 AFIX 43 H14 2 0.367432 -0.085160 0.235836 11.00000 -1.20000 AFIX 0 C15 1 0.418497 0.132771 0.191615 11.00000 0.01652 0.01253 = 0.02539 -0.00249 0.01110 0.00231 C16 1 0.199718 0.569793 0.050766 11.00000 0.01901 0.01547 = 0.02985 0.00329 0.00717 0.00365 AFIX 43 H16 2 0.243820 0.649843 0.070947 11.00000 -1.20000 AFIX 0 C17 1 0.167627 0.457098 0.086551 11.00000 0.01788 0.00924 = 0.02086 0.00023 0.01378 0.00267 C18 1 0.101656 0.333423 0.056125 11.00000 0.01581 0.02524 = 0.01961 -0.00094 0.01385 -0.00142 AFIX 43 H18 2 0.077741 0.261519 0.078306 11.00000 -1.20000 AFIX 0 C19 1 0.072748 0.319988 -0.007208 11.00000 0.01692 0.01943 = 0.02544 -0.00251 0.00799 0.00212 AFIX 43 H19 2 0.029589 0.229416 -0.028526 11.00000 -1.20000 AFIX 0 C20 1 0.108737 0.443062 -0.038824 11.00000 0.02931 0.02205 = 0.01516 0.00796 0.00625 0.00676 AFIX 43 H20 2 0.088275 0.436450 -0.081694 11.00000 -1.20000 AFIX 0 C21 1 0.200721 0.473126 0.155641 11.00000 0.01764 0.00940 = 0.02954 0.00023 0.01590 0.00487 N1 3 0.267324 0.428065 0.182929 11.00000 0.01997 0.04163 = 0.02036 -0.00144 0.00805 0.00519 AFIX 3 H1A 2 0.278849 0.349279 0.221107 11.00000 -1.50000 H1C 2 0.279168 0.270221 0.161772 11.00000 -1.50000 AFIX 0 N2 3 0.171380 0.571083 -0.011075 11.00000 0.02397 0.03055 = 0.02530 0.00068 0.01737 -0.00311 O1 4 0.809863 1.121278 0.105680 11.00000 0.02351 0.05143 = 0.03435 0.01436 0.01750 -0.00586 AFIX 147 H1 2 0.804071 1.226477 0.073870 11.00000 -1.50000 AFIX 0 O2 4 0.438403 0.434974 0.094093 11.00000 0.02890 0.04408 = 0.02577 0.00249 0.01466 -0.00372 O3 4 0.363188 0.164396 0.136748 11.00000 0.02052 0.04469 = 0.02302 0.00461 0.01218 -0.00377 AFIX 147 H3A 2 0.373327 0.272759 0.112213 11.00000 -1.50000 AFIX 0 O4 4 0.458302 -0.184331 0.348181 11.00000 0.01875 0.03649 = 0.02643 0.00381 0.01041 -0.00348 AFIX 147 H4 2 0.420153 -0.261497 0.338161 11.00000 -1.50000 AFIX 0 O5 4 0.166895 0.532786 0.185250 11.00000 0.01744 0.04698 = 0.02443 -0.00187 0.01153 0.00636 HKLF 4 REM 20151029ykdc_0m in Pn New: P2/n REM R1 = 0.1314 for 2260 Fo > 4sig(Fo) and 0.1738 for all 3086 data REM 256 parameters refined using 0 restraints END WGHT 0.0000 16.2131 REM Instructions for potential hydrogen bonds HTAB C12 O1_$1 HTAB N1 O5_$2 HTAB N1 O3 HTAB O1 N2_$3 HTAB O3 O2 HTAB O4 O5_$4 REM Highest difference peak 0.464, deepest hole -0.439, 1-sigma level 0.096 Q1 1 0.0967 0.2342 -0.0217 11.00000 0.05 0.46 Q2 1 0.2928 0.4298 0.2694 11.00000 0.05 0.38 Q3 1 0.3241 -0.2076 0.2259 11.00000 0.05 0.38 Q4 1 0.3668 0.4030 0.0262 11.00000 0.05 0.37 Q5 1 0.7500 0.3330 0.2500 10.50000 0.05 0.37 Q6 1 0.5041 -0.3679 0.3875 11.00000 0.05 0.36 Q7 1 0.5898 0.8187 0.1638 11.00000 0.05 0.36 Q8 1 0.8596 1.2435 0.1698 11.00000 0.05 0.33 Q9 1 0.1884 0.3670 0.0701 11.00000 0.05 0.33 Q10 1 0.0564 -0.0253 -0.0753 11.00000 0.05 0.33 Q11 1 0.6271 0.0925 0.1959 11.00000 0.05 0.33 Q12 1 0.8414 0.9940 0.0838 11.00000 0.05 0.33 Q13 1 0.7335 1.1294 0.1266 11.00000 0.05 0.33 Q14 1 0.4996 -0.0720 0.3658 11.00000 0.05 0.33 Q15 1 0.1388 0.7489 0.1503 11.00000 0.05 0.32 Q16 1 0.4333 -0.1749 0.2735 11.00000 0.05 0.32 Q17 1 0.4208 0.3914 0.0374 11.00000 0.05 0.32 Q18 1 0.1413 0.6576 0.2153 11.00000 0.05 0.31 Q19 1 0.5837 0.0915 0.2165 11.00000 0.05 0.31 Q20 1 0.6566 0.7547 0.0302 11.00000 0.05 0.31 ; _shelx_res_checksum 21172 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, 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 C1 C 0.7492(3) 1.0100(17) 0.1026(2) 0.0262(14) Uani 1 1 d . . C2 C 0.6898(3) 1.0284(17) 0.0496(2) 0.0283(14) Uani 1 1 d . . H2 H 0.6897 1.1209 0.0135 0.034 Uiso 1 1 calc R U C3 C 0.6307(3) 0.9092(17) 0.0504(3) 0.0294(15) Uani 1 1 d . . H3 H 0.5910 0.9209 0.0145 0.035 Uiso 1 1 calc R U C4 C 0.6289(2) 0.7718(16) 0.1037(2) 0.0238(13) Uani 1 1 d . . C5 C 0.6899(3) 0.7490(18) 0.1568(3) 0.0323(16) Uani 1 1 d . . H5 H 0.6902 0.6540 0.1927 0.039 Uiso 1 1 calc R U C6 C 0.7499(3) 0.866(2) 0.1564(3) 0.0371(18) Uani 1 1 d . . H6 H 0.7901 0.8482 0.1917 0.045 Uiso 1 1 calc R U C7 C 0.5653(2) 0.6529(16) 0.1030(3) 0.0261(14) Uani 1 1 d . . H7 H 0.5273 0.6780 0.0660 0.031 Uiso 1 1 calc R U C8 C 0.5557(3) 0.5111(16) 0.1500(2) 0.0265(14) Uani 1 1 d . . H8 H 0.5926 0.4828 0.1878 0.032 Uiso 1 1 calc R U C9 C 0.4889(3) 0.3985(16) 0.1440(2) 0.0235(13) Uani 1 1 d . . C10 C 0.4826(2) 0.2415(15) 0.1978(2) 0.0196(12) Uani 1 1 d . . C11 C 0.5364(2) 0.1997(16) 0.2560(2) 0.0228(13) Uani 1 1 d . . H11 H 0.5793 0.2695 0.2615 0.027 Uiso 1 1 calc R U C12 C 0.5278(2) 0.0587(16) 0.3051(2) 0.0244(14) Uani 1 1 d . . H12 H 0.5644 0.0358 0.3432 0.029 Uiso 1 1 calc R U C13 C 0.4637(2) -0.0507(14) 0.2978(2) 0.0164(11) Uani 1 1 d . . C14 C 0.4100(2) -0.0124(16) 0.2411(2) 0.0205(13) Uani 1 1 d . . H14 H 0.3674 -0.0852 0.2358 0.025 Uiso 1 1 calc R U C15 C 0.4185(2) 0.1328(14) 0.1916(2) 0.0174(12) Uani 1 1 d . . C16 C 0.1997(3) 0.5698(15) 0.0508(2) 0.0225(13) Uani 1 1 d . . H16 H 0.2438 0.6498 0.0709 0.027 Uiso 1 1 calc R U C17 C 0.1676(2) 0.4571(14) 0.0866(2) 0.0141(11) Uani 1 1 d . . C18 C 0.1017(2) 0.3334(15) 0.0561(2) 0.0180(12) Uani 1 1 d . . H18 H 0.0777 0.2615 0.0783 0.022 Uiso 1 1 calc R U C19 C 0.0727(2) 0.3200(15) -0.0072(2) 0.0209(13) Uani 1 1 d . . H19 H 0.0296 0.2294 -0.0285 0.025 Uiso 1 1 calc R U C20 C 0.1087(3) 0.4431(16) -0.0388(2) 0.0232(13) Uani 1 1 d . . H20 H 0.0883 0.4364 -0.0817 0.028 Uiso 1 1 calc R U C21 C 0.2007(2) 0.4731(14) 0.1556(2) 0.0168(11) Uani 1 1 d . . N1 N 0.2673(2) 0.4281(15) 0.18293(19) 0.0275(12) Uani 1 1 d . . H1A H 0.2788 0.3493 0.2211 0.041 Uiso 1 1 d R U H1C H 0.2792 0.2702 0.1618 0.041 Uiso 1 1 d R U N2 N 0.1714(2) 0.5711(14) -0.01108(19) 0.0242(11) Uani 1 1 d . . O1 O 0.80986(17) 1.1213(13) 0.10568(17) 0.0346(11) Uani 1 1 d . . H1 H 0.8041 1.2265 0.0739 0.052 Uiso 1 1 calc R U O2 O 0.43840(18) 0.4350(12) 0.09409(16) 0.0318(11) Uani 1 1 d . . O3 O 0.36319(17) 0.1644(12) 0.13675(16) 0.0284(10) Uani 1 1 d . . H3A H 0.3733 0.2728 0.1122 0.043 Uiso 1 1 calc R U O4 O 0.45830(17) -0.1843(12) 0.34818(16) 0.0269(10) Uani 1 1 d . . H4 H 0.4202 -0.2615 0.3382 0.040 Uiso 1 1 calc R U O5 O 0.16690(16) 0.5328(12) 0.18525(16) 0.0287(10) 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 0.027(3) 0.030(3) 0.028(3) 0.003(3) 0.0168(19) 0.007(3) C2 0.035(3) 0.033(4) 0.024(2) 0.004(3) 0.0190(19) 0.002(3) C3 0.019(2) 0.035(4) 0.038(3) 0.008(3) 0.015(2) -0.004(3) C4 0.023(2) 0.021(3) 0.034(3) 0.003(3) 0.0196(19) 0.012(2) C5 0.033(3) 0.035(4) 0.034(3) 0.011(3) 0.019(2) 0.000(3) C6 0.022(3) 0.057(5) 0.028(3) 0.019(3) 0.006(2) 0.009(3) C7 0.019(2) 0.022(3) 0.044(3) -0.003(3) 0.020(2) 0.002(2) C8 0.029(2) 0.024(3) 0.035(3) 0.003(3) 0.0212(19) -0.003(3) C9 0.028(3) 0.020(3) 0.028(2) -0.003(3) 0.0174(19) 0.006(2) C10 0.023(2) 0.013(3) 0.030(2) -0.002(2) 0.0181(18) 0.002(2) C11 0.016(2) 0.021(3) 0.036(3) -0.004(3) 0.0148(19) -0.002(2) C12 0.017(2) 0.029(3) 0.029(3) -0.002(3) 0.0114(19) 0.005(2) C13 0.026(2) 0.011(3) 0.022(2) 0.001(2) 0.0195(17) -0.001(2) C14 0.010(2) 0.025(3) 0.030(2) -0.002(3) 0.0121(17) 0.001(2) C15 0.017(2) 0.013(3) 0.025(2) -0.002(2) 0.0111(18) 0.002(2) C16 0.019(2) 0.015(3) 0.030(3) 0.003(3) 0.007(2) 0.004(2) C17 0.018(2) 0.009(3) 0.021(2) 0.000(2) 0.0138(16) 0.003(2) C18 0.016(2) 0.025(3) 0.020(2) -0.001(2) 0.0139(16) -0.001(2) C19 0.017(2) 0.019(3) 0.025(3) -0.003(2) 0.0080(19) 0.002(2) C20 0.029(3) 0.022(3) 0.015(2) 0.008(2) 0.0063(19) 0.007(3) C21 0.018(2) 0.009(3) 0.030(2) 0.000(2) 0.0159(17) 0.005(2) N1 0.020(2) 0.042(3) 0.020(2) -0.001(2) 0.0080(16) 0.005(2) N2 0.024(2) 0.031(3) 0.025(2) 0.001(2) 0.0174(15) -0.003(2) O1 0.0235(18) 0.051(3) 0.0344(19) 0.014(2) 0.0175(14) -0.006(2) O2 0.0289(18) 0.044(3) 0.0258(18) 0.002(2) 0.0147(14) -0.004(2) O3 0.0205(17) 0.045(3) 0.0230(17) 0.005(2) 0.0122(13) -0.0038(19) O4 0.0188(17) 0.036(2) 0.0264(18) 0.0038(19) 0.0104(13) -0.0035(18) O5 0.0174(16) 0.047(3) 0.0244(17) -0.002(2) 0.0115(13) 0.0064(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 O1 C1 C2 123.5(5) O1 C1 C6 116.1(4) C2 C1 C6 120.4(5) C3 C2 C1 119.8(5) C3 C2 H2 120.1 C1 C2 H2 120.1 C2 C3 C4 121.7(5) C2 C3 H3 119.2 C4 C3 H3 119.2 C3 C4 C5 117.7(5) C3 C4 C7 120.1(5) C5 C4 C7 122.2(5) C6 C5 C4 121.1(5) C6 C5 H5 119.4 C4 C5 H5 119.4 C5 C6 C1 119.3(5) C5 C6 H6 120.4 C1 C6 H6 120.4 C8 C7 C4 127.0(5) C8 C7 H7 116.5 C4 C7 H7 116.5 C7 C8 C9 122.4(5) C7 C8 H8 118.8 C9 C8 H8 118.8 O2 C9 C8 120.3(5) O2 C9 C10 120.6(5) C8 C9 C10 119.1(4) C11 C10 C15 117.0(5) C11 C10 C9 124.1(5) C15 C10 C9 118.9(4) C12 C11 C10 122.0(5) C12 C11 H11 119.0 C10 C11 H11 119.0 C11 C12 C13 120.0(5) C11 C12 H12 120.0 C13 C12 H12 120.0 O4 C13 C14 123.8(4) O4 C13 C12 117.2(4) C14 C13 C12 118.9(5) C13 C14 C15 121.2(5) C13 C14 H14 119.4 C15 C14 H14 119.4 O3 C15 C14 118.1(4) O3 C15 C10 121.0(5) C14 C15 C10 120.9(4) N2 C16 C17 124.3(5) N2 C16 H16 117.9 C17 C16 H16 117.9 C16 C17 C18 117.7(4) C16 C17 C21 122.2(4) C18 C17 C21 120.0(4) C19 C18 C17 118.7(5) C19 C18 H18 120.6 C17 C18 H18 120.6 C18 C19 C20 119.1(5) C18 C19 H19 120.5 C20 C19 H19 120.5 N2 C20 C19 123.6(5) N2 C20 H20 118.2 C19 C20 H20 118.2 O5 C21 N1 122.4(5) O5 C21 C17 120.5(4) N1 C21 C17 117.0(4) C21 N1 H1A 108.8 C21 N1 H1C 109.2 H1A N1 H1C 109.5 C20 N2 C16 116.5(5) C1 O1 H1 109.5 C15 O3 H3A 109.5 C13 O4 H4 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.367(6) C1 C2 1.382(7) C1 C6 1.393(8) C2 C3 1.380(8) C2 H2 0.9300 C3 C4 1.393(8) C3 H3 0.9300 C4 C5 1.405(7) C4 C7 1.456(7) C5 C6 1.390(8) C5 H5 0.9300 C6 H6 0.9300 C7 C8 1.340(8) C7 H7 0.9300 C8 C9 1.473(7) C8 H8 0.9300 C9 O2 1.246(6) C9 C10 1.475(8) C10 C11 1.403(7) C10 C15 1.410(7) C11 C12 1.376(8) C11 H11 0.9300 C12 C13 1.402(7) C12 H12 0.9300 C13 O4 1.357(6) C13 C14 1.378(6) C14 C15 1.386(7) C14 H14 0.9300 C15 O3 1.365(6) C16 N2 1.341(6) C16 C17 1.385(7) C16 H16 0.9300 C17 C18 1.397(7) C17 C21 1.500(7) C18 C19 1.374(7) C18 H18 0.9300 C19 C20 1.384(8) C19 H19 0.9300 C20 N2 1.338(7) C20 H20 0.9300 C21 O5 1.243(6) C21 N1 1.334(6) N1 H1A 0.8900 N1 H1C 0.8900 O1 H1 0.8200 O3 H3A 0.8200 O4 H4 0.8200 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 O1 C1 C2 C3 179.8(6) C6 C1 C2 C3 1.2(10) C1 C2 C3 C4 0.5(10) C2 C3 C4 C5 -1.7(9) C2 C3 C4 C7 179.2(6) C3 C4 C5 C6 1.2(10) C7 C4 C5 C6 -179.7(6) C4 C5 C6 C1 0.4(10) O1 C1 C6 C5 179.6(6) C2 C1 C6 C5 -1.6(10) C3 C4 C7 C8 179.0(6) C5 C4 C7 C8 -0.1(10) C4 C7 C8 C9 -179.8(6) C7 C8 C9 O2 -0.4(9) C7 C8 C9 C10 179.4(6) O2 C9 C10 C11 -178.2(6) C8 C9 C10 C11 1.9(8) O2 C9 C10 C15 0.1(8) C8 C9 C10 C15 -179.7(5) C15 C10 C11 C12 0.1(8) C9 C10 C11 C12 178.5(6) C10 C11 C12 C13 0.4(9) C11 C12 C13 O4 -179.4(5) C11 C12 C13 C14 -0.4(9) O4 C13 C14 C15 178.7(5) C12 C13 C14 C15 -0.3(9) C13 C14 C15 O3 -179.7(5) C13 C14 C15 C10 0.8(8) C11 C10 C15 O3 179.8(5) C9 C10 C15 O3 1.3(8) C11 C10 C15 C14 -0.8(8) C9 C10 C15 C14 -179.3(5) N2 C16 C17 C18 0.7(9) N2 C16 C17 C21 -177.7(5) C16 C17 C18 C19 1.9(8) C21 C17 C18 C19 -179.7(5) C17 C18 C19 C20 -2.7(8) C18 C19 C20 N2 1.2(9) C16 C17 C21 O5 146.2(5) C18 C17 C21 O5 -32.2(8) C16 C17 C21 N1 -32.4(8) C18 C17 C21 N1 149.2(5) C19 C20 N2 C16 1.3(9) C17 C16 N2 C20 -2.2(9)