#------------------------------------------------------------------------------ #$Date: 2024-05-05 06:59:14 +0300 (Sun, 05 May 2024) $ #$Revision: 291685 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159884.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_7159884 loop_ _publ_author_name 'Wu, Yinsong' 'Shi, Guanghao' 'Liu, Yanan' 'Kong, Yangzilin' 'Wu, Mengdi' 'Wang, Demao' 'Wu, Xiaobing' 'Shang, Yongjia' 'He, Xinwei' _publ_section_title ; A rhodium-catalyzed cascade C-H activation/annulation strategy for the expeditious assembly of pyrrolidinedione-fused 1,2-benzothiazines. ; _journal_issue 17 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3523 _journal_page_last 3532 _journal_paper_doi 10.1039/d4ob00193a _journal_volume 22 _journal_year 2024 _chemical_formula_moiety 'C19 H16 N2 O3 S' _chemical_formula_sum 'C19 H16 N2 O3 S' _chemical_formula_weight 352.40 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-10-06 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2024-01-26 deposited with the CCDC. 2024-04-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.80(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.45(2) _cell_length_b 8.899(16) _cell_length_c 17.03(3) _cell_measurement_reflns_used 7947 _cell_measurement_temperature 300.00 _cell_measurement_theta_max 27.242 _cell_measurement_theta_min 2.384 _cell_volume 1699(5) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_collection 'Bruker SMART APEX II diffractrometer' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/2 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 300.00 _diffrn_detector 'CCD area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_unetI/netI 0.0279 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 18605 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.506 _diffrn_reflns_theta_min 1.818 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1185 before and 0.0538 after correction. The Ratio of minimum to maximum transmission is 0.7131. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.379 _exptl_crystal_description block _exptl_crystal_F_000 736 _exptl_crystal_recrystallization_method 'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.306 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.043 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3868 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0391 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+0.4056P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1077 _refine_ls_wR_factor_ref 0.1160 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3156 _reflns_number_total 3868 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00193a2.cif _cod_data_source_block 330831d_0m_a _cod_depositor_comments 'Adding full bibliography for 7159884.cif.' _cod_original_cell_volume 1698(6) _cod_database_code 7159884 _shelx_shelxl_version_number 2019/2 _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_max 0.973 _shelx_estimated_absorpt_t_min 0.967 _exptl_crystal_mounting_method 'The title complex was mounted in a sealed capillary.' _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C13(H13A,H13B) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C8(H8A,H8B,H8C) ; _shelx_res_file ; TITL 330831d_0m_a.res in P2(1)/c 330831d_0m_a.res created by SHELXL-2019/2 at 08:03:21 on 06-Oct-2022 REM Old TITL 330831d_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.120, Rweak 0.003, Alpha 0.023, Orientation as input REM Formula found by SHELXT: C7 N2 O3 Cl CELL 0.71073 11.4456 8.8985 17.0303 90 101.797 90 ZERR 4 0.0217 0.0163 0.0324 0 0.031 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 76 64 8 12 4 L.S. 10 PLAN 1 SIZE 0.13 0.15 0.16 TEMP 20 CONF BOND $H LIST 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.061200 0.405600 FVAR 0.60495 S1 5 0.578759 0.353774 0.683026 11.00000 0.04075 0.03510 = 0.02793 0.00014 0.00430 -0.00063 O1 4 0.654210 0.249034 0.734859 11.00000 0.04867 0.04710 = 0.04328 0.01053 -0.00155 0.00101 O3 4 0.463783 0.142585 0.382119 11.00000 0.06422 0.07127 = 0.03897 -0.01739 0.01500 -0.00466 O4 4 0.243955 0.096913 0.576807 11.00000 0.04822 0.07342 = 0.05057 0.00241 0.01165 -0.01649 N1 3 0.447833 0.295490 0.649023 11.00000 0.03983 0.04778 = 0.03018 0.00027 0.00646 -0.00229 N2 3 0.333633 0.094551 0.466572 11.00000 0.04121 0.04301 = 0.03613 -0.00385 -0.00096 -0.00197 C1 1 0.562152 0.517135 0.737510 11.00000 0.06868 0.04405 = 0.03671 -0.00785 0.01585 -0.00239 AFIX 137 H1A 2 0.512504 0.495832 0.775263 11.00000 -1.50000 H1B 2 0.525782 0.594428 0.701304 11.00000 -1.50000 H1C 2 0.639088 0.550470 0.765756 11.00000 -1.50000 AFIX 0 C2 1 0.644072 0.405613 0.602398 11.00000 0.03783 0.03380 = 0.03431 0.00111 0.00769 0.00227 C3 1 0.601269 0.339343 0.526486 11.00000 0.03696 0.03248 = 0.03304 0.00322 0.00699 0.00679 C4 1 0.664377 0.371023 0.465382 11.00000 0.04492 0.04329 = 0.03694 0.00310 0.01212 0.00808 AFIX 43 H4 2 0.639538 0.326843 0.415255 11.00000 -1.20000 AFIX 0 C5 1 0.762528 0.466314 0.477999 11.00000 0.04383 0.04492 = 0.05408 0.00983 0.02074 0.00890 C6 1 0.801028 0.530335 0.553985 11.00000 0.04397 0.04708 = 0.06523 0.00294 0.01613 -0.00519 AFIX 43 H6 2 0.866287 0.594920 0.562744 11.00000 -1.20000 AFIX 0 C7 1 0.744158 0.499528 0.615960 11.00000 0.04595 0.04426 = 0.04722 -0.00440 0.00862 -0.00604 AFIX 43 H7 2 0.772067 0.540844 0.666474 11.00000 -1.20000 AFIX 0 C8 1 0.825393 0.503096 0.410804 11.00000 0.06539 0.07125 = 0.07381 0.00718 0.03953 0.00106 AFIX 137 H8A 2 0.821090 0.609330 0.400811 11.00000 -1.50000 H8B 2 0.787637 0.450390 0.363164 11.00000 -1.50000 H8C 2 0.907499 0.472999 0.425633 11.00000 -1.50000 AFIX 0 C9 1 0.495869 0.247053 0.516826 11.00000 0.03726 0.03643 = 0.02877 -0.00048 0.00347 0.00356 C10 1 0.435487 0.159726 0.446589 11.00000 0.04104 0.03982 = 0.03413 -0.00276 0.00373 0.00505 C11 1 0.430100 0.233794 0.574849 11.00000 0.03590 0.03479 = 0.02956 0.00295 0.00208 0.00375 C12 1 0.322618 0.135103 0.543224 11.00000 0.03771 0.04174 = 0.03661 0.00402 0.00133 0.00111 C13 1 0.251482 -0.006710 0.413562 11.00000 0.04978 0.03649 = 0.04761 -0.00587 -0.00651 0.00000 AFIX 23 H13A 2 0.221065 -0.080679 0.446124 11.00000 -1.20000 H13B 2 0.295480 -0.059969 0.379211 11.00000 -1.20000 AFIX 0 C14 1 0.147235 0.073990 0.361628 11.00000 0.04441 0.03322 = 0.04102 -0.00858 -0.00317 -0.00041 C15 1 0.161613 0.148941 0.292873 11.00000 0.05063 0.05085 = 0.04669 -0.00480 0.00341 0.00055 AFIX 43 H15 2 0.235677 0.148542 0.278393 11.00000 -1.20000 AFIX 0 C16 1 0.066877 0.224480 0.245453 11.00000 0.07549 0.05436 = 0.04879 0.00579 -0.00572 0.00219 AFIX 43 H16 2 0.077716 0.275635 0.199860 11.00000 -1.20000 AFIX 0 C17 1 -0.043909 0.223502 0.266202 11.00000 0.05563 0.05728 = 0.07747 -0.00025 -0.01529 0.01155 AFIX 43 H17 2 -0.107423 0.274613 0.234607 11.00000 -1.20000 AFIX 0 C18 1 -0.060383 0.147749 0.332924 11.00000 0.04322 0.06597 = 0.08685 -0.00367 0.00485 0.00401 AFIX 43 H18 2 -0.135363 0.145735 0.346025 11.00000 -1.20000 AFIX 0 C19 1 0.034882 0.073735 0.381193 11.00000 0.05325 0.05198 = 0.05580 -0.00202 0.00707 -0.00279 AFIX 43 H19 2 0.023503 0.023602 0.426957 11.00000 -1.20000 AFIX 0 HKLF 4 REM 330831d_0m_a.res in P2(1)/c REM wR2 = 0.1160, GooF = S = 1.053, Restrained GooF = 1.053 for all data REM R1 = 0.0391 for 3156 Fo > 4sig(Fo) and 0.0505 for all 3868 data REM 228 parameters refined using 0 restraints END WGHT 0.0611 0.4054 REM Highest difference peak 0.306, deepest hole -0.393, 1-sigma level 0.043 Q1 1 0.5656 0.4397 0.7101 11.00000 0.05 0.31 ; _shelx_res_checksum 65347 _olex2_submission_special_instructions 'No special instructions were received' 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 S1 S 0.57876(3) 0.35377(4) 0.68303(2) 0.03498(13) Uani 1 1 d . . . . . O1 O 0.65421(11) 0.24903(13) 0.73486(7) 0.0479(3) Uani 1 1 d . . . . . O3 O 0.46378(12) 0.14259(16) 0.38212(8) 0.0575(4) Uani 1 1 d . . . . . O4 O 0.24395(11) 0.09691(16) 0.57681(8) 0.0572(3) Uani 1 1 d . . . . . N1 N 0.44783(11) 0.29549(16) 0.64902(8) 0.0394(3) Uani 1 1 d . . . . . N2 N 0.33363(12) 0.09455(16) 0.46657(8) 0.0414(3) Uani 1 1 d . . . . . C1 C 0.56215(18) 0.5171(2) 0.73751(10) 0.0491(4) Uani 1 1 d . . . . . H1A H 0.512504 0.495832 0.775263 0.074 Uiso 1 1 calc R U . . . H1B H 0.525782 0.594428 0.701304 0.074 Uiso 1 1 calc R U . . . H1C H 0.639088 0.550470 0.765756 0.074 Uiso 1 1 calc R U . . . C2 C 0.64407(14) 0.40561(17) 0.60240(9) 0.0353(3) Uani 1 1 d . . . . . C3 C 0.60127(13) 0.33934(16) 0.52649(9) 0.0342(3) Uani 1 1 d . . . . . C4 C 0.66438(15) 0.37102(18) 0.46538(10) 0.0412(4) Uani 1 1 d . . . . . H4 H 0.639538 0.326843 0.415255 0.049 Uiso 1 1 calc R U . . . C5 C 0.76253(15) 0.4663(2) 0.47800(11) 0.0461(4) Uani 1 1 d . . . . . C6 C 0.80103(16) 0.5303(2) 0.55398(12) 0.0514(4) Uani 1 1 d . . . . . H6 H 0.866287 0.594920 0.562744 0.062 Uiso 1 1 calc R U . . . C7 C 0.74416(15) 0.49953(19) 0.61596(11) 0.0459(4) Uani 1 1 d . . . . . H7 H 0.772067 0.540844 0.666474 0.055 Uiso 1 1 calc R U . . . C8 C 0.82539(19) 0.5031(3) 0.41080(14) 0.0665(6) Uani 1 1 d . . . . . H8A H 0.821090 0.609330 0.400811 0.100 Uiso 1 1 calc R U . . . H8B H 0.787637 0.450390 0.363164 0.100 Uiso 1 1 calc R U . . . H8C H 0.907499 0.472999 0.425633 0.100 Uiso 1 1 calc R U . . . C9 C 0.49587(14) 0.24705(17) 0.51683(9) 0.0346(3) Uani 1 1 d . . . . . C10 C 0.43549(14) 0.15973(18) 0.44659(10) 0.0389(4) Uani 1 1 d . . . . . C11 C 0.43010(13) 0.23379(16) 0.57485(9) 0.0341(3) Uani 1 1 d . . . . . C12 C 0.32262(14) 0.13510(18) 0.54322(10) 0.0396(4) Uani 1 1 d . . . . . C13 C 0.25148(16) -0.00671(19) 0.41356(11) 0.0470(4) Uani 1 1 d . . . . . H13A H 0.221065 -0.080679 0.446124 0.056 Uiso 1 1 calc R U . . . H13B H 0.295480 -0.059969 0.379211 0.056 Uiso 1 1 calc R U . . . C14 C 0.14724(15) 0.07399(17) 0.36163(10) 0.0412(4) Uani 1 1 d . . . . . C15 C 0.16161(17) 0.1489(2) 0.29287(11) 0.0503(4) Uani 1 1 d . . . . . H15 H 0.235677 0.148542 0.278393 0.060 Uiso 1 1 calc R U . . . C16 C 0.0669(2) 0.2245(2) 0.24545(12) 0.0622(5) Uani 1 1 d . . . . . H16 H 0.077716 0.275635 0.199860 0.075 Uiso 1 1 calc R U . . . C17 C -0.04391(19) 0.2235(2) 0.26620(14) 0.0676(6) Uani 1 1 d . . . . . H17 H -0.107423 0.274613 0.234607 0.081 Uiso 1 1 calc R U . . . C18 C -0.06038(18) 0.1477(3) 0.33292(15) 0.0665(6) Uani 1 1 d . . . . . H18 H -0.135363 0.145735 0.346025 0.080 Uiso 1 1 calc R U . . . C19 C 0.03488(17) 0.0737(2) 0.38119(12) 0.0543(5) Uani 1 1 d . . . . . H19 H 0.023503 0.023602 0.426957 0.065 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 S1 0.0408(2) 0.0351(2) 0.0279(2) 0.00014(14) 0.00430(15) -0.00063(14) O1 0.0487(7) 0.0471(6) 0.0433(7) 0.0105(5) -0.0016(5) 0.0010(5) O3 0.0642(8) 0.0713(9) 0.0390(7) -0.0174(6) 0.0150(6) -0.0047(7) O4 0.0482(7) 0.0734(9) 0.0506(8) 0.0024(7) 0.0116(6) -0.0165(6) N1 0.0398(7) 0.0478(8) 0.0302(7) 0.0003(6) 0.0065(5) -0.0023(6) N2 0.0412(7) 0.0430(7) 0.0361(7) -0.0039(6) -0.0010(6) -0.0020(6) C1 0.0687(12) 0.0440(9) 0.0367(9) -0.0078(7) 0.0158(8) -0.0024(8) C2 0.0378(8) 0.0338(7) 0.0343(8) 0.0011(6) 0.0077(6) 0.0023(6) C3 0.0370(8) 0.0325(7) 0.0330(8) 0.0032(6) 0.0070(6) 0.0068(6) C4 0.0449(9) 0.0433(9) 0.0369(8) 0.0031(7) 0.0121(7) 0.0081(7) C5 0.0438(9) 0.0449(9) 0.0541(10) 0.0098(8) 0.0207(8) 0.0089(7) C6 0.0440(9) 0.0471(10) 0.0652(12) 0.0029(9) 0.0161(8) -0.0052(8) C7 0.0459(9) 0.0443(9) 0.0472(10) -0.0044(7) 0.0086(8) -0.0060(7) C8 0.0654(13) 0.0712(14) 0.0738(14) 0.0072(11) 0.0395(11) 0.0011(11) C9 0.0373(7) 0.0364(8) 0.0288(7) -0.0005(6) 0.0035(6) 0.0036(6) C10 0.0410(8) 0.0398(8) 0.0341(8) -0.0028(6) 0.0037(7) 0.0051(6) C11 0.0359(7) 0.0348(8) 0.0296(7) 0.0029(6) 0.0021(6) 0.0037(6) C12 0.0377(8) 0.0417(8) 0.0366(8) 0.0040(7) 0.0013(7) 0.0011(6) C13 0.0498(9) 0.0365(8) 0.0476(10) -0.0059(7) -0.0065(8) 0.0000(7) C14 0.0444(8) 0.0332(8) 0.0410(9) -0.0086(7) -0.0032(7) -0.0004(6) C15 0.0506(10) 0.0508(10) 0.0467(10) -0.0048(8) 0.0034(8) 0.0006(8) C16 0.0755(14) 0.0544(11) 0.0488(11) 0.0058(9) -0.0057(10) 0.0022(10) C17 0.0556(12) 0.0573(12) 0.0775(15) -0.0002(11) -0.0153(11) 0.0116(10) C18 0.0432(10) 0.0660(14) 0.0869(16) -0.0037(11) 0.0048(10) 0.0040(9) C19 0.0533(10) 0.0520(11) 0.0558(11) -0.0020(9) 0.0071(9) -0.0028(8) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 N1 114.61(12) . . ? O1 S1 C1 109.11(15) . . ? O1 S1 C2 110.56(13) . . ? N1 S1 C1 105.58(11) . . ? N1 S1 C2 108.88(13) . . ? C2 S1 C1 107.79(13) . . ? C11 N1 S1 115.16(12) . . ? C10 N2 C13 124.21(17) . . ? C12 N2 C10 111.15(14) . . ? C12 N2 C13 124.62(16) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 S1 118.85(16) . . ? C7 C2 S1 119.58(15) . . ? C7 C2 C3 121.27(15) . . ? C2 C3 C9 117.88(15) . . ? C4 C3 C2 117.19(18) . . ? C4 C3 C9 124.93(16) . . ? C3 C4 H4 119.1 . . ? C5 C4 C3 121.85(18) . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 118.90(17) . . ? C4 C5 C8 120.8(2) . . ? C6 C5 C8 120.3(2) . . ? C5 C6 H6 119.4 . . ? C7 C6 C5 121.3(2) . . ? C7 C6 H6 119.4 . . ? C2 C7 H7 120.3 . . ? C6 C7 C2 119.49(18) . . ? C6 C7 H7 120.3 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 C10 129.47(15) . . ? C11 C9 C3 122.66(16) . . ? C11 C9 C10 107.79(18) . . ? O3 C10 N2 123.66(15) . . ? O3 C10 C9 129.15(18) . . ? N2 C10 C9 107.19(16) . . ? N1 C11 C9 129.87(17) . . ? N1 C11 C12 121.44(14) . . ? C9 C11 C12 108.68(17) . . ? O4 C12 N2 126.33(17) . . ? O4 C12 C11 128.48(18) . . ? N2 C12 C11 105.18(15) . . ? N2 C13 H13A 108.9 . . ? N2 C13 H13B 108.9 . . ? N2 C13 C14 113.37(18) . . ? H13A C13 H13B 107.7 . . ? C14 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C15 C14 C13 120.42(19) . . ? C15 C14 C19 118.53(17) . . ? C19 C14 C13 121.0(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C15 C16 H16 120.1 . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 120.1 . . ? C16 C17 H17 119.9 . . ? C18 C17 C16 120.30(19) . . ? C18 C17 H17 119.9 . . ? C17 C18 H18 120.0 . . ? C17 C18 C19 120.0(2) . . ? C19 C18 H18 120.0 . . ? C14 C19 H19 119.7 . . ? C18 C19 C14 120.6(2) . . ? C18 C19 H19 119.7 . . ? 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 S1 O1 1.443(2) . ? S1 N1 1.580(3) . ? S1 C1 1.756(3) . ? S1 C2 1.754(3) . ? O3 C10 1.216(3) . ? O4 C12 1.210(3) . ? N1 C11 1.354(3) . ? N2 C10 1.405(3) . ? N2 C12 1.385(3) . ? N2 C13 1.471(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.414(3) . ? C2 C7 1.399(3) . ? C3 C4 1.411(3) . ? C3 C9 1.441(3) . ? C4 H4 0.9300 . ? C4 C5 1.389(3) . ? C5 C6 1.400(3) . ? C5 C8 1.507(3) . ? C6 H6 0.9300 . ? C6 C7 1.376(3) . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.475(3) . ? C9 C11 1.364(3) . ? C11 C12 1.518(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.513(3) . ? C14 C15 1.386(3) . ? C14 C19 1.393(4) . ? C15 H15 0.9300 . ? C15 C16 1.386(3) . ? C16 H16 0.9300 . ? C16 C17 1.384(4) . ? C17 H17 0.9300 . ? C17 C18 1.367(4) . ? C18 H18 0.9300 . ? C18 C19 1.390(3) . ? C19 H19 0.9300 . ? 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 S1 N1 C11 C9 -18.7(2) . . . . ? S1 N1 C11 C12 162.79(12) . . . . ? S1 C2 C3 C4 -173.20(11) . . . . ? S1 C2 C3 C9 7.84(19) . . . . ? S1 C2 C7 C6 174.81(13) . . . . ? O1 S1 N1 C11 -96.18(16) . . . . ? O1 S1 C2 C3 102.15(18) . . . . ? O1 S1 C2 C7 -71.67(19) . . . . ? N1 S1 C2 C3 -24.61(15) . . . . ? N1 S1 C2 C7 161.57(13) . . . . ? N1 C11 C12 O4 -1.4(3) . . . . ? N1 C11 C12 N2 179.40(13) . . . . ? N2 C13 C14 C15 79.2(2) . . . . ? N2 C13 C14 C19 -101.4(2) . . . . ? C1 S1 N1 C11 143.72(12) . . . . ? C1 S1 C2 C3 -138.67(14) . . . . ? C1 S1 C2 C7 47.51(16) . . . . ? C2 S1 N1 C11 28.22(15) . . . . ? C2 C3 C4 C5 -1.7(2) . . . . ? C2 C3 C9 C10 -176.91(14) . . . . ? C2 C3 C9 C11 6.7(2) . . . . ? C3 C2 C7 C6 1.1(3) . . . . ? C3 C4 C5 C6 1.2(2) . . . . ? C3 C4 C5 C8 -177.57(16) . . . . ? C3 C9 C10 O3 2.7(3) . . . . ? C3 C9 C10 N2 -177.47(15) . . . . ? C3 C9 C11 N1 -1.5(3) . . . . ? C3 C9 C11 C12 177.10(13) . . . . ? C4 C3 C9 C10 4.2(3) . . . . ? C4 C3 C9 C11 -172.18(14) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C5 C6 C7 C2 -1.7(3) . . . . ? C7 C2 C3 C4 0.5(2) . . . . ? C7 C2 C3 C9 -178.45(14) . . . . ? C8 C5 C6 C7 179.32(17) . . . . ? C9 C3 C4 C5 177.18(15) . . . . ? C9 C11 C12 O4 179.78(17) . . . . ? C9 C11 C12 N2 0.62(17) . . . . ? C10 N2 C12 O4 179.77(16) . . . . ? C10 N2 C12 C11 -1.05(17) . . . . ? C10 N2 C13 C14 -92.5(2) . . . . ? C10 C9 C11 N1 -178.62(15) . . . . ? C10 C9 C11 C12 0.02(16) . . . . ? C11 C9 C10 O3 179.48(17) . . . . ? C11 C9 C10 N2 -0.65(17) . . . . ? C12 N2 C10 O3 -179.03(16) . . . . ? C12 N2 C10 C9 1.09(17) . . . . ? C12 N2 C13 C14 89.2(2) . . . . ? C13 N2 C10 O3 2.5(2) . . . . ? C13 N2 C10 C9 -177.40(13) . . . . ? C13 N2 C12 O4 -1.7(3) . . . . ? C13 N2 C12 C11 177.43(13) . . . . ? C13 C14 C15 C16 -179.30(16) . . . . ? C13 C14 C19 C18 -179.76(17) . . . . ? C14 C15 C16 C17 -0.9(3) . . . . ? C15 C14 C19 C18 -0.3(3) . . . . ? C15 C16 C17 C18 -0.4(3) . . . . ? C16 C17 C18 C19 1.3(3) . . . . ? C17 C18 C19 C14 -0.9(3) . . . . ? C19 C14 C15 C16 1.2(3) . . . . ?