#------------------------------------------------------------------------------ #$Date: 2016-10-08 01:30:48 +0300 (Sat, 08 Oct 2016) $ #$Revision: 187154 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119063.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_7119063 loop_ _publ_author_name 'Wu, Z. L.' 'Fang, Y. L.' 'Tang, Y. T.' 'Xiao, M. W.' 'Ye, J.' 'Li, G. X.' 'Hu, A. X.' _publ_section_title ; Synthesis and antitumor evaluation of 5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)-N-arylthiazol-2-amines ; _journal_issue 9 _journal_name_full 'Med. Chem. Commun.' _journal_page_first 1768 _journal_paper_doi 10.1039/C6MD00234J _journal_volume 7 _journal_year 2016 _chemical_formula_moiety 'C25 H25 N3 O2 S' _chemical_formula_sum 'C25 H25 N3 O2 S' _chemical_formula_weight 431.54 _chemical_melting_point 427.0(10) _chemical_name_systematic 5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)-N-(2-methylquinolin-8-yl)thiazol-2-amine _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-I 2ya' _symmetry_space_group_name_H-M 'I 1 2/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _audit_update_record ; 2016-04-25 deposited with the CCDC. 2016-06-24 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 119.209(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 19.2951(9) _cell_length_b 13.6381(4) _cell_length_c 19.3808(8) _cell_measurement_reflns_used 5772 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.2430 _cell_measurement_theta_min 3.5320 _cell_volume 4451.5(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) ; _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2005)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 10.5058 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 12031 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.99 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_T_max 0.9390 _exptl_absorpt_correction_T_min 0.9327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1824 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.37 _refine_diff_density_max 0.411 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 297 _refine_ls_number_reflns 4371 _refine_ls_number_restraints 14 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0430 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+5.2330P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1074 _refine_ls_wR_factor_ref 0.1164 _reflns_number_gt 3649 _reflns_number_total 4371 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL 10102F in I2/a #15 CELL 0.71073 19.295091 13.638146 19.380847 90.0000 119.2092 90.0000 ZERR 8 0.000873 0.000380 0.000772 0.0000 0.0054 0.0000 LATT 2 SYMM 0.5-X,+Y,-Z SFAC C H N O S UNIT 200 200 24 16 8 OMIT -3 52 L.S. 8 ACTA bond $h FMAP 2 PLAN 1 conf htab size 0.41 0.38 0.37 DFIX 1.54 0.02 C11 C13 C11 C13B ISOR 0.005 C13 C13B WGHT 0.053000 5.229300 FVAR 2.510630 0.496550 temp -123 ; _cod_data_source_file c6md00234j2.cif _cod_data_source_block 10102f _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '426-428' was changed to '427.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas Adding full bibliography for 7119063.cif. ; _cod_original_cell_volume 4451.5(3) _cod_database_code 7119063 _solvent_exptl_crystal_recrystallization_method ethanol loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.07882(12) 0.16701(15) -0.07897(12) 0.0310(5) Uani 1 1 d . . . H1A H 0.0819 0.0945 -0.0770 0.037 Uiso 1 1 calc R . . H1B H 0.0582 0.1881 -0.1345 0.037 Uiso 1 1 calc R . . C2 C 0.14412(11) 0.28206(14) 0.01164(10) 0.0230(4) Uani 1 1 d . . . C3 C 0.19773(11) 0.35002(14) 0.05997(10) 0.0229(4) Uani 1 1 d . . . H3 H 0.2504 0.3515 0.0679 0.027 Uiso 1 1 calc R . . C4 C 0.17236(10) 0.41772(13) 0.09750(10) 0.0202(4) Uani 1 1 d . . . C5 C 0.09561(11) 0.41243(14) 0.08576(11) 0.0252(4) Uani 1 1 d . . . H5 H 0.0792 0.4582 0.1119 0.030 Uiso 1 1 calc R . . C6 C 0.04143(11) 0.34137(15) 0.03637(11) 0.0273(4) Uani 1 1 d . . . H6 H -0.0110 0.3379 0.0287 0.033 Uiso 1 1 calc R . . C7 C 0.06749(11) 0.27759(14) -0.00011(10) 0.0231(4) Uani 1 1 d . . . C8 C 0.23111(11) 0.49607(14) 0.14730(11) 0.0242(4) Uani 1 1 d . . . H8A H 0.2811 0.4633 0.1854 0.029 Uiso 1 1 calc R . . H8B H 0.2430 0.5369 0.1121 0.029 Uiso 1 1 calc R . . C9 C 0.20601(10) 0.56310(13) 0.19300(10) 0.0216(4) Uani 1 1 d . A . C10 C 0.21089(11) 0.55787(13) 0.26514(11) 0.0235(4) Uani 1 1 d . A . C11 C 0.24399(13) 0.47748(16) 0.32771(12) 0.0362(5) Uani 1 1 d D . . C12 C 0.3141(2) 0.5219(2) 0.40286(15) 0.0732(10) Uani 1 1 d . A . H12A H 0.2952 0.5780 0.4208 0.110 Uiso 1 1 calc R . . H12B H 0.3554 0.5438 0.3908 0.110 Uiso 1 1 calc R . . H12C H 0.3361 0.4722 0.4446 0.110 Uiso 1 1 calc R . . C13 C 0.1867(5) 0.4530(6) 0.3548(5) 0.038(2) Uani 0.50(2) 1 d PDU A 1 H13A H 0.2048 0.4811 0.4074 0.057 Uiso 0.50(2) 1 calc PR A 1 H13B H 0.1827 0.3816 0.3573 0.057 Uiso 0.50(2) 1 calc PR A 1 H13C H 0.1345 0.4800 0.3176 0.057 Uiso 0.50(2) 1 calc PR A 1 C13B C 0.1654(7) 0.4290(9) 0.3238(10) 0.066(3) Uani 0.50(2) 1 d PDU A 2 H13D H 0.1296 0.4066 0.2698 0.100 Uiso 0.50(2) 1 calc PR A 2 H13E H 0.1383 0.4781 0.3391 0.100 Uiso 0.50(2) 1 calc PR A 2 H13F H 0.1809 0.3732 0.3601 0.100 Uiso 0.50(2) 1 calc PR A 2 C14 C 0.27714(15) 0.38901(17) 0.30490(14) 0.0451(6) Uani 1 1 d . A . H14A H 0.2955 0.3397 0.3469 0.068 Uiso 1 1 calc R . . H14B H 0.3218 0.4099 0.2976 0.068 Uiso 1 1 calc R . . H14C H 0.2355 0.3608 0.2555 0.068 Uiso 1 1 calc R . . C15 C 0.15216(10) 0.70334(13) 0.23009(10) 0.0202(4) Uani 1 1 d . A . C16 C 0.11637(11) 0.83459(13) 0.29562(10) 0.0216(4) Uani 1 1 d . A . C17 C 0.14696(11) 0.79418(15) 0.37024(11) 0.0264(4) Uani 1 1 d . . . H17 H 0.1713 0.7314 0.3810 0.032 Uiso 1 1 calc R . . C18 C 0.14186(12) 0.84661(16) 0.43051(11) 0.0319(5) Uani 1 1 d . . . H18 H 0.1634 0.8183 0.4817 0.038 Uiso 1 1 calc R . . C19 C 0.10696(12) 0.93654(16) 0.41740(12) 0.0334(5) Uani 1 1 d . . . H19 H 0.1039 0.9699 0.4589 0.040 Uiso 1 1 calc R . . C20 C 0.07529(11) 0.97995(15) 0.34183(12) 0.0287(4) Uani 1 1 d . . . C21 C 0.08033(10) 0.92984(14) 0.28058(11) 0.0229(4) Uani 1 1 d . . . C22 C 0.02201(11) 1.05746(15) 0.19219(12) 0.0308(5) Uani 1 1 d . . . C23 C 0.01427(13) 1.11223(16) 0.25013(14) 0.0397(5) Uani 1 1 d . . . H23 H -0.0088 1.1758 0.2379 0.048 Uiso 1 1 calc R . . C24 C 0.03988(13) 1.07379(17) 0.32311(14) 0.0383(5) Uani 1 1 d . . . H24 H 0.0340 1.1101 0.3618 0.046 Uiso 1 1 calc R . . C25 C -0.00627(14) 1.09925(17) 0.11139(14) 0.0415(5) Uani 1 1 d . . . H25A H 0.0056 1.0532 0.0797 0.062 Uiso 1 1 calc R . . H25B H 0.0208 1.1616 0.1158 0.062 Uiso 1 1 calc R . . H25C H -0.0637 1.1103 0.0858 0.062 Uiso 1 1 calc R . . N1 N 0.18035(9) 0.63844(12) 0.28573(9) 0.0245(3) Uani 1 1 d . . . N2 N 0.11789(10) 0.79077(12) 0.23165(9) 0.0232(3) Uani 1 1 d . . . N3 N 0.05356(9) 0.96866(11) 0.20685(9) 0.0246(3) Uani 1 1 d . . . O1 O 0.02726(8) 0.20054(11) -0.05012(8) 0.0332(3) Uani 1 1 d . . . O2 O 0.15550(8) 0.20815(11) -0.03017(9) 0.0374(4) Uani 1 1 d . . . S1 S 0.16064(3) 0.67300(3) 0.14740(2) 0.02271(14) Uani 1 1 d . . . H2 H 0.0999(12) 0.8276(16) 0.1910(12) 0.026(6) Uiso 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 0.0256(10) 0.0312(11) 0.0318(10) -0.0112(8) 0.0106(8) -0.0005(9) C2 0.0227(9) 0.0232(9) 0.0221(9) -0.0016(7) 0.0101(7) 0.0037(8) C3 0.0185(9) 0.0261(10) 0.0254(9) -0.0011(7) 0.0118(7) 0.0008(8) C4 0.0210(9) 0.0184(9) 0.0198(8) 0.0012(7) 0.0090(7) 0.0006(7) C5 0.0238(10) 0.0272(10) 0.0281(9) -0.0049(8) 0.0153(8) 0.0000(8) C6 0.0198(9) 0.0330(11) 0.0318(10) -0.0055(8) 0.0146(8) -0.0032(8) C7 0.0214(9) 0.0242(10) 0.0214(9) -0.0030(7) 0.0086(7) -0.0044(8) C8 0.0220(9) 0.0223(9) 0.0290(9) -0.0029(7) 0.0130(8) -0.0002(8) C9 0.0177(9) 0.0186(9) 0.0251(9) -0.0015(7) 0.0079(7) -0.0017(7) C10 0.0219(9) 0.0209(9) 0.0270(9) 0.0003(7) 0.0113(8) -0.0005(8) C11 0.0438(13) 0.0333(12) 0.0348(11) 0.0133(9) 0.0220(10) 0.0138(10) C12 0.094(2) 0.0604(19) 0.0336(13) 0.0097(13) 0.0061(14) 0.0233(18) C13 0.038(3) 0.040(3) 0.041(3) 0.018(2) 0.023(2) 0.003(2) C13B 0.074(4) 0.060(4) 0.084(5) 0.043(3) 0.053(4) 0.024(3) C14 0.0537(15) 0.0358(13) 0.0471(13) 0.0158(10) 0.0256(12) 0.0148(11) C15 0.0193(9) 0.0210(9) 0.0200(8) -0.0034(7) 0.0092(7) -0.0038(7) C16 0.0199(9) 0.0221(9) 0.0247(9) -0.0068(7) 0.0123(7) -0.0070(7) C17 0.0261(10) 0.0289(10) 0.0252(9) -0.0044(8) 0.0134(8) -0.0062(8) C18 0.0303(11) 0.0436(12) 0.0243(10) -0.0076(9) 0.0154(8) -0.0109(10) C19 0.0308(11) 0.0433(13) 0.0328(11) -0.0185(9) 0.0209(9) -0.0128(10) C20 0.0199(9) 0.0324(11) 0.0363(11) -0.0151(9) 0.0157(8) -0.0082(8) C21 0.0160(9) 0.0241(9) 0.0291(9) -0.0089(8) 0.0113(7) -0.0069(7) C22 0.0203(10) 0.0238(10) 0.0436(11) -0.0056(9) 0.0119(9) -0.0013(8) C23 0.0319(12) 0.0270(11) 0.0569(14) -0.0100(10) 0.0193(10) 0.0037(9) C24 0.0304(11) 0.0370(12) 0.0505(13) -0.0213(10) 0.0221(10) -0.0046(10) C25 0.0386(13) 0.0287(11) 0.0497(13) 0.0052(10) 0.0156(10) 0.0073(10) N1 0.0277(8) 0.0241(8) 0.0227(8) 0.0018(6) 0.0129(7) 0.0020(7) N2 0.0300(9) 0.0196(8) 0.0206(8) -0.0002(6) 0.0127(7) 0.0021(7) N3 0.0201(8) 0.0215(8) 0.0306(8) -0.0041(6) 0.0110(7) -0.0032(7) O1 0.0254(7) 0.0367(8) 0.0368(8) -0.0176(6) 0.0146(6) -0.0084(6) O2 0.0245(8) 0.0429(9) 0.0421(8) -0.0243(7) 0.0142(6) -0.0027(7) S1 0.0287(3) 0.0203(2) 0.0200(2) -0.00022(17) 0.01249(19) 0.00211(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' S S 0.1246 0.1234 '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 O2 C1 O1 107.99(14) O2 C1 H1A 110.1 O1 C1 H1A 110.1 O2 C1 H1B 110.1 O1 C1 H1B 110.1 H1A C1 H1B 108.4 C3 C2 O2 128.06(17) C3 C2 C7 122.30(17) O2 C2 C7 109.62(16) C2 C3 C4 117.63(17) C2 C3 H3 121.2 C4 C3 H3 121.2 C5 C4 C3 119.72(17) C5 C4 C8 123.31(16) C3 C4 C8 116.94(16) C4 C5 C6 121.89(17) C4 C5 H5 119.1 C6 C5 H5 119.1 C7 C6 C5 116.99(17) C7 C6 H6 121.5 C5 C6 H6 121.5 C6 C7 O1 128.73(17) C6 C7 C2 121.48(17) O1 C7 C2 109.77(16) C9 C8 C4 116.57(15) C9 C8 H8A 108.1 C4 C8 H8A 108.1 C9 C8 H8B 108.1 C4 C8 H8B 108.1 H8A C8 H8B 107.3 C10 C9 C8 133.86(17) C10 C9 S1 109.44(14) C8 C9 S1 116.70(13) C9 C10 N1 115.29(16) C9 C10 C11 130.46(17) N1 C10 C11 114.25(16) C13 C11 C10 110.5(3) C13 C11 C14 114.6(4) C10 C11 C14 114.18(17) C13 C11 C12 102.5(4) C10 C11 C12 107.52(19) C14 C11 C12 106.5(2) C10 C11 C13B 103.7(4) C14 C11 C13B 100.3(5) C12 C11 C13B 124.8(7) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C11 C13 H13A 109.5 C11 C13 H13B 109.5 H13A C13 H13B 109.5 C11 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C11 C13B H13D 109.5 C11 C13B H13E 109.5 H13D C13B H13E 109.5 C11 C13B H13F 109.5 H13D C13B H13F 109.5 H13E C13B H13F 109.5 C11 C14 H14A 109.5 C11 C14 H14B 109.5 H14A C14 H14B 109.5 C11 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 N1 C15 N2 126.06(16) N1 C15 S1 114.56(14) N2 C15 S1 119.38(13) C17 C16 N2 125.31(17) C17 C16 C21 119.38(16) N2 C16 C21 115.30(16) C16 C17 C18 119.78(19) C16 C17 H17 120.1 C18 C17 H17 120.1 C19 C18 C17 121.92(19) C19 C18 H18 119.0 C17 C18 H18 119.0 C18 C19 C20 119.68(18) C18 C19 H19 120.2 C20 C19 H19 120.2 C24 C20 C19 123.80(18) C24 C20 C21 116.45(19) C19 C20 C21 119.73(19) N3 C21 C20 123.01(18) N3 C21 C16 117.48(15) C20 C21 C16 119.50(17) N3 C22 C23 121.9(2) N3 C22 C25 117.90(18) C23 C22 C25 120.21(19) C24 C23 C22 119.8(2) C24 C23 H23 120.1 C22 C23 H23 120.1 C23 C24 C20 120.18(19) C23 C24 H24 119.9 C20 C24 H24 119.9 C22 C25 H25A 109.5 C22 C25 H25B 109.5 H25A C25 H25B 109.5 C22 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C15 N1 C10 111.45(15) C15 N2 C16 127.89(16) C15 N2 H2 118.4(14) C16 N2 H2 113.3(14) C22 N3 C21 118.60(16) C7 O1 C1 104.87(14) C2 O2 C1 105.46(14) C15 S1 C9 89.26(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O2 1.426(2) C1 O1 1.433(2) C1 H1A 0.9900 C1 H1B 0.9900 C2 C3 1.364(3) C2 O2 1.376(2) C2 C7 1.383(3) C3 C4 1.403(2) C3 H3 0.9500 C4 C5 1.386(3) C4 C8 1.513(2) C5 C6 1.404(3) C5 H5 0.9500 C6 C7 1.362(3) C6 H6 0.9500 C7 O1 1.383(2) C8 C9 1.508(2) C8 H8A 0.9900 C8 H8B 0.9900 C9 C10 1.357(3) C9 S1 1.7432(18) C10 N1 1.394(2) C10 C11 1.525(3) C11 C13 1.475(7) C11 C14 1.528(3) C11 C12 1.548(4) C11 C13B 1.621(10) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C13B H13D 0.9800 C13B H13E 0.9800 C13B H13F 0.9800 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 N1 1.292(2) C15 N2 1.371(2) C15 S1 1.7386(17) C16 C17 1.382(3) C16 N2 1.389(2) C16 C21 1.435(3) C17 C18 1.413(3) C17 H17 0.9500 C18 C19 1.362(3) C18 H18 0.9500 C19 C20 1.413(3) C19 H19 0.9500 C20 C24 1.412(3) C20 C21 1.413(3) C21 N3 1.367(2) C22 N3 1.323(3) C22 C23 1.416(3) C22 C25 1.497(3) C23 C24 1.356(3) C23 H23 0.9500 C24 H24 0.9500 C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 N2 H2 0.85(2) 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 O2 C2 C3 C4 -178.99(17) C7 C2 C3 C4 -0.9(3) C2 C3 C4 C5 1.2(3) C2 C3 C4 C8 -176.71(16) C3 C4 C5 C6 -0.6(3) C8 C4 C5 C6 177.13(18) C4 C5 C6 C7 -0.3(3) C5 C6 C7 O1 178.82(18) C5 C6 C7 C2 0.6(3) C3 C2 C7 C6 -0.1(3) O2 C2 C7 C6 178.37(18) C3 C2 C7 O1 -178.55(17) O2 C2 C7 O1 -0.1(2) C5 C4 C8 C9 7.3(3) C3 C4 C8 C9 -174.91(16) C4 C8 C9 C10 86.8(3) C4 C8 C9 S1 -93.46(18) C8 C9 C10 N1 179.33(18) S1 C9 C10 N1 -0.4(2) C8 C9 C10 C11 -1.2(4) S1 C9 C10 C11 179.07(18) C9 C10 C11 C13 -130.7(5) N1 C10 C11 C13 48.8(5) C9 C10 C11 C14 0.3(3) N1 C10 C11 C14 179.77(18) C9 C10 C11 C12 118.2(3) N1 C10 C11 C12 -62.3(2) C9 C10 C11 C13B -107.9(7) N1 C10 C11 C13B 71.6(7) N2 C16 C17 C18 179.79(17) C21 C16 C17 C18 0.5(3) C16 C17 C18 C19 0.4(3) C17 C18 C19 C20 -0.5(3) C18 C19 C20 C24 -178.31(19) C18 C19 C20 C21 -0.2(3) C24 C20 C21 N3 0.6(3) C19 C20 C21 N3 -177.63(17) C24 C20 C21 C16 179.33(17) C19 C20 C21 C16 1.1(3) C17 C16 C21 N3 177.56(16) N2 C16 C21 N3 -1.8(2) C17 C16 C21 C20 -1.2(3) N2 C16 C21 C20 179.40(16) N3 C22 C23 C24 0.2(3) C25 C22 C23 C24 179.9(2) C22 C23 C24 C20 0.9(3) C19 C20 C24 C23 176.8(2) C21 C20 C24 C23 -1.3(3) N2 C15 N1 C10 179.92(17) S1 C15 N1 C10 -0.4(2) C9 C10 N1 C15 0.5(2) C11 C10 N1 C15 -179.04(16) N1 C15 N2 C16 10.2(3) S1 C15 N2 C16 -169.46(14) C17 C16 N2 C15 -3.3(3) C21 C16 N2 C15 176.07(17) C23 C22 N3 C21 -0.9(3) C25 C22 N3 C21 179.41(17) C20 C21 N3 C22 0.5(3) C16 C21 N3 C22 -178.24(16) C6 C7 O1 C1 172.6(2) C2 C7 O1 C1 -9.0(2) O2 C1 O1 C7 14.7(2) C3 C2 O2 C1 -172.41(19) C7 C2 O2 C1 9.3(2) O1 C1 O2 C2 -14.8(2) N1 C15 S1 C9 0.14(15) N2 C15 S1 C9 179.84(15) C10 C9 S1 C15 0.17(14) C8 C9 S1 C15 -179.64(14)