#------------------------------------------------------------------------------ #$Date: 2025-01-06 16:12:40 +0200 (Mon, 06 Jan 2025) $ #$Revision: 297138 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/35/1573533.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_1573533 loop_ _publ_author_name 'Rodríguez Saravia, Magdalena' 'Martínez, Verónica' 'Vairoletti, Franco' 'Macías, Mario' 'Davyt, Danilo' 'Hernández Dossi, Gonzalo' 'Mahler, Graciela' _publ_section_title ; Novel enantiopure δ-thiolactones: synthesis, structural characterization, and reactivity studies. ; _journal_issue 54 _journal_name_full 'RSC advances' _journal_page_first 40287 _journal_page_last 40298 _journal_paper_doi 10.1039/d4ra07780f _journal_volume 14 _journal_year 2024 _chemical_absolute_configuration syn _chemical_formula_moiety 'C7 H9 N O S3' _chemical_formula_sum 'C7 H9 N O S3' _chemical_formula_weight 219.33 _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 direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-09-27 deposited with the CCDC. 2024-12-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.900(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4682(5) _cell_length_b 5.3017(3) _cell_length_c 15.1947(7) _cell_measurement_reflns_used 9887 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 72.00 _cell_measurement_theta_min 3.86 _cell_volume 923.34(8) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0490 _diffrn_reflns_av_unetI/netI 0.0406 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 15886 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.968 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.310 _diffrn_reflns_theta_min 2.910 _exptl_absorpt_coefficient_mu 6.941 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.4212 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.578 _exptl_crystal_description plate _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.595 _exptl_crystal_size_mid 0.134 _exptl_crystal_size_min 0.103 _refine_diff_density_max 0.421 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.070(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 3542 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0523P)^2^+0.3779P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1019 _refine_ls_wR_factor_ref 0.1049 _reflns_Friedel_coverage 0.743 _reflns_Friedel_fraction_full 0.952 _reflns_Friedel_fraction_max 0.932 _reflns_number_gt 3270 _reflns_number_total 3542 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ra07780f2.cif _cod_data_source_block Compound_1a _cod_depositor_comments 'Adding full bibliography for 1573533--1573534.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1573533 _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 0.104 _shelx_estimated_absorpt_t_max 0.535 _shelx_res_file ; TITL cu_200203_AP_VE229_0m_a.res in P2(1) cu_200203_AP_VE229_0m_a.res created by SHELXL-2018/3 at 18:34:04 on 14-Feb-2024 REM Old TITL cu_200203_AP_VE229_0m in P2(1) REM SHELXT solution in P2(1) REM R1 0.136, Rweak 0.025, Alpha 0.001, Orientation as input REM Flack x = 0.149 ( 0.011 ) from Parsons' quotients REM Formula found by SHELXT: C14 N2 O2 S6 CELL 1.54178 11.4682 5.3017 15.1947 90 91.9 90 ZERR 4 0.0005 0.0003 0.0007 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 28 36 4 4 12 L.S. 10 PLAN 10 SIZE 0.103 0.134 0.595 TEMP 25 BOND $H LIST 4 fmap 2 acta conf WGHT 0.052300 0.377900 FVAR 0.19333 S3B 5 0.107917 1.264077 0.503999 11.00000 0.05089 0.06038 = 0.05399 0.00697 -0.00714 0.00678 S10 5 0.550301 0.362709 0.848842 11.00000 0.05689 0.05774 = 0.07100 0.01945 -0.00994 0.00515 S10B 5 0.395007 0.707390 0.499826 11.00000 0.06458 0.05550 = 0.05448 0.00210 0.00611 0.00873 S6 5 0.883223 -0.188497 1.007771 11.00000 0.05969 0.07430 = 0.04432 0.00897 -0.00469 0.01937 S3 5 0.814925 -0.137401 0.729133 11.00000 0.07545 0.08837 = 0.03596 -0.01478 0.00734 -0.01470 S6B 5 0.183276 1.080380 0.776019 11.00000 0.08128 0.10457 = 0.03698 -0.01040 0.00644 0.00322 N1 3 0.770826 0.062768 0.880429 11.00000 0.04080 0.04855 = 0.02733 0.00199 -0.00184 -0.00436 O1 4 0.582575 0.385819 1.017527 11.00000 0.07010 0.06638 = 0.07019 -0.00465 0.01100 0.01933 N1B 3 0.225057 0.958478 0.612406 11.00000 0.04653 0.05585 = 0.03553 0.00043 -0.00324 0.00112 C5 1 0.880779 -0.075338 0.894757 11.00000 0.03663 0.05600 = 0.04082 -0.00561 0.00120 -0.00506 AFIX 13 H5 2 0.945802 0.042300 0.888067 11.00000 -1.20000 AFIX 0 C8 1 0.695922 0.054212 0.957033 11.00000 0.04915 0.04644 = 0.03532 0.00649 0.00408 0.00264 AFIX 13 H8 2 0.650005 -0.101659 0.954418 11.00000 -1.20000 AFIX 0 C11 1 0.640161 0.215940 0.765604 11.00000 0.06501 0.06570 = 0.04414 0.01204 -0.01688 -0.01686 AFIX 23 H11A 2 0.590636 0.166856 0.715514 11.00000 -1.20000 H11B 2 0.696067 0.338467 0.745345 11.00000 -1.20000 AFIX 0 O1B 4 0.484941 0.630986 0.653659 11.00000 0.10489 0.13304 = 0.06743 0.01247 -0.00965 0.04916 C9 1 0.613766 0.275600 0.953233 11.00000 0.04597 0.04718 = 0.05522 0.00535 0.00428 -0.00078 C2B 1 0.242428 1.095232 0.530005 11.00000 0.04684 0.04798 = 0.04357 0.00587 -0.00243 -0.00090 AFIX 13 H2B 2 0.306760 1.215542 0.538140 11.00000 -1.20000 AFIX 0 C2 1 0.705222 -0.014384 0.800657 11.00000 0.04699 0.05176 = 0.03378 0.00082 -0.00390 -0.01648 AFIX 13 H2 2 0.649650 -0.147686 0.814731 11.00000 -1.20000 AFIX 0 C7 1 0.776814 0.044912 1.036970 11.00000 0.07067 0.06593 = 0.03362 0.00223 -0.00121 0.01518 AFIX 23 H7A 2 0.735604 -0.006034 1.088787 11.00000 -1.20000 H7B 2 0.813287 0.207473 1.047940 11.00000 -1.20000 AFIX 0 C5B 1 0.129892 1.060066 0.662511 11.00000 0.04782 0.06747 = 0.04568 -0.00720 0.00412 -0.00703 AFIX 13 H5B 2 0.064563 0.940911 0.659216 11.00000 -1.20000 AFIX 0 C4 1 0.887917 -0.278128 0.824897 11.00000 0.05357 0.06731 = 0.05402 -0.01369 0.00926 -0.00116 AFIX 23 H4A 2 0.848336 -0.430576 0.842734 11.00000 -1.20000 H4B 2 0.968432 -0.318281 0.813120 11.00000 -1.20000 AFIX 0 C8B 1 0.335105 0.936011 0.661661 11.00000 0.05050 0.05842 = 0.04222 0.00429 -0.00840 -0.00596 AFIX 13 H8B 2 0.374650 1.099886 0.661937 11.00000 -1.20000 AFIX 0 C9B 1 0.410998 0.744009 0.616324 11.00000 0.05083 0.05601 = 0.06463 0.00528 0.00173 0.00891 C7B 1 0.305813 0.868873 0.754377 11.00000 0.07068 0.08212 = 0.03770 0.00170 -0.01110 -0.00083 AFIX 23 H7BA 2 0.371313 0.900443 0.794910 11.00000 -1.20000 H7BB 2 0.282833 0.693371 0.758802 11.00000 -1.20000 AFIX 0 C11B 1 0.272744 0.903610 0.461832 11.00000 0.07288 0.06461 = 0.03948 0.00260 -0.00196 0.00592 AFIX 23 H11C 2 0.292847 0.989278 0.408004 11.00000 -1.20000 H11D 2 0.205431 0.797580 0.448817 11.00000 -1.20000 AFIX 0 C4B 1 0.090206 1.308471 0.621925 11.00000 0.06845 0.06707 = 0.06410 -0.00674 0.00286 0.01798 AFIX 23 H4BA 2 0.138135 1.446869 0.644012 11.00000 -1.20000 H4BB 2 0.009375 1.342602 0.634588 11.00000 -1.20000 AFIX 0 HKLF 4 REM cu_200203_AP_VE229_0m_a.res in P2(1) REM wR2 = 0.1049, GooF = S = 1.062, Restrained GooF = 1.062 for all data REM R1 = 0.0387 for 3270 Fo > 4sig(Fo) and 0.0425 for all 3542 data REM 217 parameters refined using 1 restraints END WGHT 0.0523 0.3779 REM Highest difference peak 0.421, deepest hole -0.304, 1-sigma level 0.053 Q1 1 0.1330 1.2208 0.7605 11.00000 0.05 0.42 Q2 1 0.4234 0.7331 0.6758 11.00000 0.05 0.40 Q3 1 0.5821 0.3304 0.8054 11.00000 0.05 0.39 Q4 1 0.2641 1.1195 0.6173 11.00000 0.05 0.38 Q5 1 0.8625 -0.2513 0.7394 11.00000 0.05 0.36 Q6 1 0.3811 0.7331 0.5585 11.00000 0.05 0.32 Q7 1 0.1441 1.1004 0.4878 11.00000 0.05 0.27 Q8 1 0.2629 0.8982 0.5378 11.00000 0.05 0.25 Q9 1 0.8392 -0.0127 0.7320 11.00000 0.05 0.24 Q10 1 0.8342 -0.3177 0.9967 11.00000 0.05 0.24 ; _shelx_res_checksum 65410 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 S3B S 0.10792(10) 1.2641(2) 0.50400(8) 0.0553(3) Uani 1 1 d . . . . . S10 S 0.55030(10) 0.3627(3) 0.84884(9) 0.0621(3) Uani 1 1 d . . . . . S10B S 0.39501(11) 0.7074(3) 0.49983(8) 0.0581(3) Uani 1 1 d . . . . . S6 S 0.88322(11) -0.1885(3) 1.00777(7) 0.0596(4) Uani 1 1 d . . . . . S3 S 0.81492(12) -0.1374(3) 0.72913(7) 0.0665(4) Uani 1 1 d . . . . . S6B S 0.18328(13) 1.0804(4) 0.77602(8) 0.0742(4) Uani 1 1 d . . . . . N1 N 0.7708(3) 0.0628(7) 0.88043(19) 0.0390(7) Uani 1 1 d . . . . . O1 O 0.5826(3) 0.3858(8) 1.0175(3) 0.0687(10) Uani 1 1 d . . . . . N1B N 0.2251(3) 0.9585(8) 0.6124(2) 0.0461(9) Uani 1 1 d . . . . . C5 C 0.8808(3) -0.0753(9) 0.8948(3) 0.0445(10) Uani 1 1 d . . . . . H5 H 0.945802 0.042300 0.888067 0.053 Uiso 1 1 calc R U . . . C8 C 0.6959(4) 0.0542(9) 0.9570(3) 0.0436(9) Uani 1 1 d . . . . . H8 H 0.650005 -0.101659 0.954418 0.052 Uiso 1 1 calc R U . . . C11 C 0.6402(4) 0.2159(11) 0.7656(3) 0.0587(13) Uani 1 1 d . . . . . H11A H 0.590636 0.166856 0.715514 0.070 Uiso 1 1 calc R U . . . H11B H 0.696067 0.338467 0.745345 0.070 Uiso 1 1 calc R U . . . O1B O 0.4849(5) 0.6310(12) 0.6537(3) 0.1021(19) Uani 1 1 d . . . . . C9 C 0.6138(4) 0.2756(10) 0.9532(3) 0.0494(10) Uani 1 1 d . . . . . C2B C 0.2424(4) 1.0952(10) 0.5300(3) 0.0462(10) Uani 1 1 d . . . . . H2B H 0.306760 1.215542 0.538140 0.055 Uiso 1 1 calc R U . . . C2 C 0.7052(4) -0.0144(9) 0.8007(3) 0.0443(10) Uani 1 1 d . . . . . H2 H 0.649650 -0.147686 0.814731 0.053 Uiso 1 1 calc R U . . . C7 C 0.7768(4) 0.0449(11) 1.0370(3) 0.0568(12) Uani 1 1 d . . . . . H7A H 0.735604 -0.006034 1.088787 0.068 Uiso 1 1 calc R U . . . H7B H 0.813287 0.207473 1.047940 0.068 Uiso 1 1 calc R U . . . C5B C 0.1299(4) 1.0601(11) 0.6625(3) 0.0536(11) Uani 1 1 d . . . . . H5B H 0.064563 0.940911 0.659216 0.064 Uiso 1 1 calc R U . . . C4 C 0.8879(4) -0.2781(12) 0.8249(3) 0.0581(12) Uani 1 1 d . . . . . H4A H 0.848336 -0.430576 0.842734 0.070 Uiso 1 1 calc R U . . . H4B H 0.968432 -0.318281 0.813120 0.070 Uiso 1 1 calc R U . . . C8B C 0.3351(4) 0.9360(10) 0.6617(3) 0.0506(11) Uani 1 1 d . . . . . H8B H 0.374650 1.099886 0.661937 0.061 Uiso 1 1 calc R U . . . C9B C 0.4110(4) 0.7440(11) 0.6163(3) 0.0572(12) Uani 1 1 d . . . . . C7B C 0.3058(4) 0.8689(14) 0.7544(3) 0.0638(14) Uani 1 1 d . . . . . H7BA H 0.371313 0.900443 0.794910 0.077 Uiso 1 1 calc R U . . . H7BB H 0.282833 0.693371 0.758802 0.077 Uiso 1 1 calc R U . . . C11B C 0.2727(5) 0.9036(11) 0.4618(3) 0.0591(13) Uani 1 1 d . . . . . H11C H 0.292847 0.989278 0.408004 0.071 Uiso 1 1 calc R U . . . H11D H 0.205431 0.797580 0.448817 0.071 Uiso 1 1 calc R U . . . C4B C 0.0902(5) 1.3085(13) 0.6219(3) 0.0665(14) Uani 1 1 d . . . . . H4BA H 0.138135 1.446869 0.644012 0.080 Uiso 1 1 calc R U . . . H4BB H 0.009375 1.342602 0.634588 0.080 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 S3B 0.0509(6) 0.0604(8) 0.0540(6) 0.0070(5) -0.0071(5) 0.0068(5) S10 0.0569(6) 0.0577(8) 0.0710(7) 0.0195(6) -0.0099(5) 0.0052(6) S10B 0.0646(7) 0.0555(8) 0.0545(6) 0.0021(5) 0.0061(5) 0.0087(6) S6 0.0597(6) 0.0743(9) 0.0443(5) 0.0090(6) -0.0047(4) 0.0194(6) S3 0.0754(8) 0.0884(11) 0.0360(5) -0.0148(6) 0.0073(5) -0.0147(8) S6B 0.0813(9) 0.1046(13) 0.0370(6) -0.0104(7) 0.0064(5) 0.0032(8) N1 0.0408(16) 0.049(2) 0.0273(14) 0.0020(14) -0.0018(12) -0.0044(15) O1 0.070(2) 0.066(3) 0.070(2) -0.005(2) 0.0110(17) 0.019(2) N1B 0.0465(18) 0.056(2) 0.0355(17) 0.0004(16) -0.0032(14) 0.0011(16) C5 0.0366(18) 0.056(3) 0.041(2) -0.0056(18) 0.0012(15) -0.0051(18) C8 0.049(2) 0.046(3) 0.0353(19) 0.0065(18) 0.0041(16) 0.0026(19) C11 0.065(3) 0.066(3) 0.044(2) 0.012(2) -0.017(2) -0.017(3) O1B 0.105(3) 0.133(5) 0.067(2) 0.012(3) -0.010(2) 0.049(4) C9 0.046(2) 0.047(3) 0.055(2) 0.005(2) 0.0043(18) -0.0008(19) C2B 0.047(2) 0.048(3) 0.044(2) 0.006(2) -0.0024(17) -0.0009(19) C2 0.047(2) 0.052(3) 0.0338(19) 0.0008(17) -0.0039(16) -0.0165(19) C7 0.071(3) 0.066(3) 0.034(2) 0.002(2) -0.0012(19) 0.015(3) C5B 0.048(2) 0.067(3) 0.046(2) -0.007(2) 0.0041(18) -0.007(2) C4 0.054(2) 0.067(3) 0.054(3) -0.014(2) 0.009(2) -0.001(2) C8B 0.051(2) 0.058(3) 0.042(2) 0.004(2) -0.0084(18) -0.006(2) C9B 0.051(2) 0.056(3) 0.065(3) 0.005(2) 0.002(2) 0.009(2) C7B 0.071(3) 0.082(4) 0.038(2) 0.002(3) -0.011(2) -0.001(3) C11B 0.073(3) 0.065(4) 0.039(2) 0.003(2) -0.002(2) 0.006(3) C4B 0.068(3) 0.067(4) 0.064(3) -0.007(3) 0.003(2) 0.018(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 C2B S3B C4B 88.4(2) . . ? C9 S10 C11 106.4(2) . . ? C9B S10B C11B 107.7(2) . . ? C7 S6 C5 90.9(2) . . ? C2 S3 C4 88.7(2) . . ? C5B S6B C7B 91.7(2) . . ? C2 N1 C5 113.5(3) . . ? C2 N1 C8 110.4(3) . . ? C5 N1 C8 112.9(3) . . ? C8B N1B C5B 114.5(3) . . ? C8B N1B C2B 109.9(3) . . ? C5B N1B C2B 112.9(4) . . ? N1 C5 C4 108.4(3) . . ? N1 C5 S6 106.9(3) . . ? C4 C5 S6 115.3(4) . . ? N1 C5 H5 108.7 . . ? C4 C5 H5 108.7 . . ? S6 C5 H5 108.7 . . ? N1 C8 C7 106.2(4) . . ? N1 C8 C9 109.1(4) . . ? C7 C8 C9 115.2(4) . . ? N1 C8 H8 108.7 . . ? C7 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? C2 C11 S10 112.4(3) . . ? C2 C11 H11A 109.1 . . ? S10 C11 H11A 109.1 . . ? C2 C11 H11B 109.1 . . ? S10 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? O1 C9 C8 123.4(4) . . ? O1 C9 S10 118.2(4) . . ? C8 C9 S10 118.2(3) . . ? N1B C2B C11B 107.2(4) . . ? N1B C2B S3B 106.9(3) . . ? C11B C2B S3B 113.5(3) . . ? N1B C2B H2B 109.7 . . ? C11B C2B H2B 109.7 . . ? S3B C2B H2B 109.7 . . ? N1 C2 C11 107.4(4) . . ? N1 C2 S3 104.4(3) . . ? C11 C2 S3 115.0(3) . . ? N1 C2 H2 109.9 . . ? C11 C2 H2 109.9 . . ? S3 C2 H2 109.9 . . ? C8 C7 S6 103.2(3) . . ? C8 C7 H7A 111.1 . . ? S6 C7 H7A 111.1 . . ? C8 C7 H7B 111.1 . . ? S6 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? N1B C5B C4B 109.2(4) . . ? N1B C5B S6B 106.5(3) . . ? C4B C5B S6B 115.0(4) . . ? N1B C5B H5B 108.7 . . ? C4B C5B H5B 108.7 . . ? S6B C5B H5B 108.7 . . ? C5 C4 S3 103.6(4) . . ? C5 C4 H4A 111.0 . . ? S3 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? S3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? N1B C8B C7B 106.6(4) . . ? N1B C8B C9B 108.8(4) . . ? C7B C8B C9B 114.6(5) . . ? N1B C8B H8B 108.9 . . ? C7B C8B H8B 108.9 . . ? C9B C8B H8B 108.9 . . ? O1B C9B C8B 122.7(5) . . ? O1B C9B S10B 118.3(4) . . ? C8B C9B S10B 118.8(3) . . ? C8B C7B S6B 102.7(4) . . ? C8B C7B H7BA 111.2 . . ? S6B C7B H7BA 111.2 . . ? C8B C7B H7BB 111.2 . . ? S6B C7B H7BB 111.2 . . ? H7BA C7B H7BB 109.1 . . ? C2B C11B S10B 111.2(3) . . ? C2B C11B H11C 109.4 . . ? S10B C11B H11C 109.4 . . ? C2B C11B H11D 109.4 . . ? S10B C11B H11D 109.4 . . ? H11C C11B H11D 108.0 . . ? C5B C4B S3B 104.2(4) . . ? C5B C4B H4BA 110.9 . . ? S3B C4B H4BA 110.9 . . ? C5B C4B H4BB 110.9 . . ? S3B C4B H4BB 110.9 . . ? H4BA C4B H4BB 108.9 . . ? 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 S3B C2B 1.816(5) . ? S3B C4B 1.825(5) . ? S10 C9 1.784(5) . ? S10 C11 1.831(6) . ? S10B C9B 1.784(5) . ? S10B C11B 1.824(5) . ? S6 C7 1.804(5) . ? S6 C5 1.818(4) . ? S3 C2 1.811(5) . ? S3 C4 1.815(6) . ? S6B C5B 1.814(5) . ? S6B C7B 1.836(6) . ? N1 C2 1.464(5) . ? N1 C5 1.468(5) . ? N1 C8 1.470(5) . ? O1 C9 1.203(6) . ? N1B C8B 1.451(5) . ? N1B C5B 1.455(6) . ? N1B C2B 1.466(6) . ? C5 C4 1.515(7) . ? C5 H5 0.9800 . ? C8 C7 1.505(6) . ? C8 C9 1.505(6) . ? C8 H8 0.9800 . ? C11 C2 1.518(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? O1B C9B 1.170(6) . ? C2B C11B 1.500(7) . ? C2B H2B 0.9800 . ? C2 H2 0.9800 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C5B C4B 1.518(8) . ? C5B H5B 0.9800 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C8B C7B 1.502(6) . ? C8B C9B 1.519(7) . ? C8B H8B 0.9800 . ? C7B H7BA 0.9700 . ? C7B H7BB 0.9700 . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? C4B H4BA 0.9700 . ? C4B H4BB 0.9700 . ? 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 C2 N1 C5 C4 -5.2(5) . . . . ? C8 N1 C5 C4 121.5(4) . . . . ? C2 N1 C5 S6 -130.1(3) . . . . ? C8 N1 C5 S6 -3.5(4) . . . . ? C7 S6 C5 N1 -20.6(3) . . . . ? C7 S6 C5 C4 -141.3(4) . . . . ? C2 N1 C8 C7 160.5(4) . . . . ? C5 N1 C8 C7 32.2(5) . . . . ? C2 N1 C8 C9 -74.8(5) . . . . ? C5 N1 C8 C9 156.9(4) . . . . ? C9 S10 C11 C2 24.3(4) . . . . ? N1 C8 C9 O1 -144.9(5) . . . . ? C7 C8 C9 O1 -25.6(7) . . . . ? N1 C8 C9 S10 40.4(5) . . . . ? C7 C8 C9 S10 159.6(4) . . . . ? C11 S10 C9 O1 166.9(4) . . . . ? C11 S10 C9 C8 -18.1(4) . . . . ? C8B N1B C2B C11B 88.9(5) . . . . ? C5B N1B C2B C11B -141.9(4) . . . . ? C8B N1B C2B S3B -149.1(3) . . . . ? C5B N1B C2B S3B -19.9(5) . . . . ? C4B S3B C2B N1B 34.4(4) . . . . ? C4B S3B C2B C11B 152.4(4) . . . . ? C5 N1 C2 C11 -148.2(4) . . . . ? C8 N1 C2 C11 83.9(4) . . . . ? C5 N1 C2 S3 -25.7(4) . . . . ? C8 N1 C2 S3 -153.6(3) . . . . ? S10 C11 C2 N1 -54.0(4) . . . . ? S10 C11 C2 S3 -169.7(2) . . . . ? C4 S3 C2 N1 38.8(3) . . . . ? C4 S3 C2 C11 156.2(4) . . . . ? N1 C8 C7 S6 -45.5(5) . . . . ? C9 C8 C7 S6 -166.4(3) . . . . ? C5 S6 C7 C8 38.0(4) . . . . ? C8B N1B C5B C4B 116.9(5) . . . . ? C2B N1B C5B C4B -10.0(5) . . . . ? C8B N1B C5B S6B -7.8(5) . . . . ? C2B N1B C5B S6B -134.7(3) . . . . ? C7B S6B C5B N1B -16.2(4) . . . . ? C7B S6B C5B C4B -137.3(4) . . . . ? N1 C5 C4 S3 33.4(4) . . . . ? S6 C5 C4 S3 153.2(2) . . . . ? C2 S3 C4 C5 -41.7(3) . . . . ? C5B N1B C8B C7B 34.7(6) . . . . ? C2B N1B C8B C7B 163.1(4) . . . . ? C5B N1B C8B C9B 158.7(4) . . . . ? C2B N1B C8B C9B -72.9(5) . . . . ? N1B C8B C9B O1B -155.1(6) . . . . ? C7B C8B C9B O1B -35.9(8) . . . . ? N1B C8B C9B S10B 30.2(6) . . . . ? C7B C8B C9B S10B 149.4(4) . . . . ? C11B S10B C9B O1B 179.5(6) . . . . ? C11B S10B C9B C8B -5.5(5) . . . . ? N1B C8B C7B S6B -43.5(5) . . . . ? C9B C8B C7B S6B -163.9(4) . . . . ? C5B S6B C7B C8B 34.3(4) . . . . ? N1B C2B C11B S10B -53.1(4) . . . . ? S3B C2B C11B S10B -171.0(3) . . . . ? C9B S10B C11B C2B 16.8(5) . . . . ? N1B C5B C4B S3B 34.8(5) . . . . ? S6B C5B C4B S3B 154.4(3) . . . . ? C2B S3B C4B C5B -39.3(4) . . . . ?