#------------------------------------------------------------------------------ #$Date: 2024-11-08 03:42:07 +0200 (Fri, 08 Nov 2024) $ #$Revision: 295829 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160221.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_7160221 loop_ _publ_author_name 'Dolas, Atul Jankiram' 'Yadav, Jyothi' 'Nagare, Yadav Kacharu' 'Rangan, Krishnan' 'Iype, Eldhose' 'Kumar, Indresh' _publ_section_title ; Enantioselective synthesis of -(3-pyrrolyl)methanamines with aza-tetrasubstituted center under metal-free conditions ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01729C _journal_year 2024 _chemical_formula_moiety 'C13 H14 N2 O3 S' _chemical_formula_sum 'C13 H14 N2 O3 S' _chemical_formula_weight 278.32 _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 2023-02-02 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2024-06-07 deposited with the CCDC. 2024-11-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.644(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0312(2) _cell_length_b 16.1924(3) _cell_length_c 9.2203(2) _cell_measurement_reflns_used 4146 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 79.2810 _cell_measurement_theta_min 4.9050 _cell_volume 1336.37(5) _computing_cell_refinement 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 133(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -29.00 13.00 0.50 1.03 -- 0.00 -57.00-120.00 84 2 \w -88.00 -52.00 0.50 1.03 -- 0.00 -57.00-120.00 72 3 \w -87.00 -49.00 0.50 1.03 -- 0.00 -57.00 -30.00 76 4 \w -39.00 20.00 0.50 1.03 -- 0.00 -57.00 -30.00 118 5 \w 36.00 139.00 0.50 4.11 -- 107.20 -82.00 -30.00 206 6 \w 84.00 150.00 0.50 4.11 -- 107.20 15.00 90.00 132 7 \w 91.00 127.00 0.50 4.11 -- 107.20 -30.00 -30.00 72 8 \w 26.00 52.00 0.50 4.11 -- 107.20 -82.00 -90.00 52 9 \w 52.00 85.00 0.50 4.11 -- 107.20 -30.00 -30.00 66 10 \w 68.00 108.00 0.50 4.11 -- 107.20 -82.00 -90.00 80 11 \w 21.00 135.00 0.50 4.11 -- 107.20 -15.00-120.00 228 12 \w 20.00 56.00 0.50 4.11 -- 107.20 -30.00 -90.00 72 13 \w 83.00 110.00 0.50 4.11 -- 107.20 -30.00 -90.00 54 14 \w 20.00 132.00 0.50 4.11 -- 107.20 -61.00 -30.00 224 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0783438000 _diffrn_orient_matrix_UB_12 -0.0113111000 _diffrn_orient_matrix_UB_13 -0.1576453000 _diffrn_orient_matrix_UB_21 0.1531228000 _diffrn_orient_matrix_UB_22 -0.0020923000 _diffrn_orient_matrix_UB_23 -0.0561990000 _diffrn_orient_matrix_UB_31 0.0058049000 _diffrn_orient_matrix_UB_32 -0.0944594000 _diffrn_orient_matrix_UB_33 0.0201268000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0363 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.966 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7241 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.966 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.568 _diffrn_reflns_theta_min 4.941 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.217 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.383 _exptl_crystal_description block _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.564 _refine_diff_density_min -0.703 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2808 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0404 _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^)+(0.0549P)^2^+0.6433P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1101 _refine_ls_wR_factor_ref 0.1129 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2508 _reflns_number_total 2808 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01729c2.cif _cod_data_source_block exp_1355_ad-686_20230202 _cod_database_code 7160221 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C13 H14 N2 O3 S' _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 0.897 _shelx_estimated_absorpt_t_min 0.793 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C7(H7) 2.b Secondary CH2 refined with riding coordinates: C12(H12A,H12B) 2.c Aromatic/amide H refined with riding coordinates: N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C) ; _shelx_res_file ; TITL exp_1355_ad-686_20230202_a.res in P2(1)/c exp_1355_ad-686_20230202.res created by SHELXL-2018/3 at 17:12:05 on 02-Feb-2023 REM Old TITL exp_1355_AD-686_20230202 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.106, Rweak 0.006, Alpha 0.017 REM 0.388 for 109 systematic absences, Orientation as input REM Formula found by SHELXT: C13 N2 O3 S CELL 1.54184 9.0312 16.1924 9.2203 90 97.644 90 ZERR 4 0.0002 0.0003 0.0002 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S UNIT 52 56 8 12 4 L.S. 4 0 0 PLAN 1 SIZE 0.11 0.07 0.05 TEMP -140(2) CONF list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.054900 0.643300 FVAR 0.40967 S1 5 0.291419 0.427526 0.506358 11.00000 0.02761 0.02144 = 0.02489 -0.00556 0.00278 -0.00276 O1 4 0.353413 0.369208 0.639897 11.00000 0.03466 0.02212 = 0.03024 -0.00597 0.00012 0.00718 O2 4 0.140399 0.405275 0.460492 11.00000 0.03026 0.03041 = 0.03039 -0.00594 -0.00102 -0.00389 O3 4 0.398600 0.420176 0.407402 11.00000 0.03821 0.03609 = 0.03672 -0.01480 0.01472 -0.00873 N1 3 0.296113 0.517968 0.576550 11.00000 0.03505 0.01820 = 0.02633 -0.00252 0.00845 -0.00391 AFIX 43 H1 2 0.349136 0.558533 0.546249 11.00000 -1.20000 AFIX 0 N2 3 0.206341 0.740993 0.832149 11.00000 0.03572 0.01687 = 0.02850 -0.00485 0.00479 -0.00193 C1 1 0.290356 0.380871 0.771044 11.00000 0.02957 0.01897 = 0.02669 -0.00243 -0.00311 0.00076 C2 1 0.226461 0.455713 0.804091 11.00000 0.02534 0.01749 = 0.02462 0.00007 0.00013 -0.00120 C3 1 0.173686 0.460957 0.939063 11.00000 0.03705 0.02410 = 0.02963 0.00035 0.00618 -0.00091 AFIX 43 H3 2 0.131048 0.511358 0.966190 11.00000 -1.20000 AFIX 0 C4 1 0.181695 0.394619 1.034889 11.00000 0.04961 0.03360 = 0.02940 0.00558 0.00565 -0.00509 AFIX 43 H4 2 0.144515 0.399675 1.126140 11.00000 -1.20000 AFIX 0 C5 1 0.244301 0.320844 0.996736 11.00000 0.06290 0.02460 = 0.03374 0.00886 -0.00604 -0.00256 AFIX 43 H5 2 0.249227 0.275125 1.061772 11.00000 -1.20000 AFIX 0 C6 1 0.299552 0.313512 0.864579 11.00000 0.04911 0.01954 = 0.03382 0.00089 -0.00943 0.00376 AFIX 43 H6 2 0.343072 0.263190 0.838295 11.00000 -1.20000 AFIX 0 C7 1 0.203049 0.527905 0.697812 11.00000 0.02506 0.01685 = 0.02342 -0.00106 0.00204 0.00019 AFIX 13 H7 2 0.095831 0.527524 0.653370 11.00000 -1.20000 AFIX 0 C8 1 0.235173 0.610550 0.767221 11.00000 0.02990 0.01622 = 0.02392 -0.00051 0.00418 -0.00211 C9 1 0.138891 0.676564 0.754202 11.00000 0.02988 0.01881 = 0.02478 -0.00225 0.00414 -0.00222 AFIX 43 H9 2 0.041746 0.677238 0.700065 11.00000 -1.20000 AFIX 0 C10 1 0.345661 0.717359 0.892986 11.00000 0.03840 0.02392 = 0.03572 -0.00459 -0.00422 -0.00607 AFIX 43 H10 2 0.416068 0.751185 0.951307 11.00000 -1.20000 AFIX 0 C11 1 0.367371 0.636670 0.856068 11.00000 0.03377 0.02254 = 0.03747 -0.00218 -0.00384 -0.00107 AFIX 43 H11 2 0.454249 0.604408 0.884497 11.00000 -1.20000 AFIX 0 C12 1 0.143713 0.824182 0.837849 11.00000 0.04301 0.01983 = 0.04040 -0.00905 0.00845 0.00219 AFIX 23 H12A 2 0.168168 0.846356 0.938240 11.00000 -1.20000 H12B 2 0.033567 0.821080 0.815410 11.00000 -1.20000 AFIX 0 C13 1 0.202570 0.882203 0.731654 11.00000 0.07330 0.02609 = 0.03823 0.00548 0.00658 0.01105 AFIX 137 H13A 2 0.174139 0.862020 0.631622 11.00000 -1.50000 H13B 2 0.311703 0.885057 0.752764 11.00000 -1.50000 H13C 2 0.160216 0.937333 0.741384 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_1355_ad-686_20230202_a.res in P2(1)/c REM wR2 = 0.1129, GooF = S = 1.086, Restrained GooF = 1.086 for all data REM R1 = 0.0404 for 2508 Fo > 4sig(Fo) and 0.0440 for all 2808 data REM 173 parameters refined using 0 restraints END WGHT 0.0549 0.6432 REM Highest difference peak 0.564, deepest hole -0.703, 1-sigma level 0.056 Q1 1 0.4028 0.5358 0.6035 11.00000 0.05 0.56 ; _shelx_res_checksum 8127 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.014 _oxdiff_exptl_absorpt_empirical_full_min 0.763 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 0.29142(4) 0.42753(2) 0.50636(4) 0.02471(14) Uani 1 1 d . . . . . O1 O 0.35341(14) 0.36921(7) 0.63990(14) 0.0294(3) Uani 1 1 d . . . . . O2 O 0.14040(14) 0.40528(8) 0.46049(14) 0.0308(3) Uani 1 1 d . . . . . O3 O 0.39860(16) 0.42018(8) 0.40740(16) 0.0361(3) Uani 1 1 d . . . . . N1 N 0.29611(17) 0.51797(8) 0.57655(16) 0.0261(3) Uani 1 1 d . . . . . H1 H 0.349136 0.558533 0.546249 0.031 Uiso 1 1 calc R U . . . N2 N 0.20634(17) 0.74099(8) 0.83215(16) 0.0270(3) Uani 1 1 d . . . . . C1 C 0.29036(19) 0.38087(10) 0.77104(19) 0.0257(3) Uani 1 1 d . . . . . C2 C 0.22646(18) 0.45571(10) 0.80409(18) 0.0228(3) Uani 1 1 d . . . . . C3 C 0.1737(2) 0.46096(11) 0.9391(2) 0.0301(4) Uani 1 1 d . . . . . H3 H 0.131048 0.511358 0.966190 0.036 Uiso 1 1 calc R U . . . C4 C 0.1817(2) 0.39462(12) 1.0349(2) 0.0375(4) Uani 1 1 d . . . . . H4 H 0.144515 0.399675 1.126140 0.045 Uiso 1 1 calc R U . . . C5 C 0.2443(3) 0.32084(12) 0.9967(2) 0.0415(5) Uani 1 1 d . . . . . H5 H 0.249227 0.275125 1.061772 0.050 Uiso 1 1 calc R U . . . C6 C 0.2996(2) 0.31351(11) 0.8646(2) 0.0355(4) Uani 1 1 d . . . . . H6 H 0.343072 0.263190 0.838295 0.043 Uiso 1 1 calc R U . . . C7 C 0.20305(18) 0.52790(9) 0.69781(17) 0.0219(3) Uani 1 1 d . . . . . H7 H 0.095831 0.527524 0.653370 0.026 Uiso 1 1 calc R U . . . C8 C 0.23517(19) 0.61055(9) 0.76722(18) 0.0233(3) Uani 1 1 d . . . . . C9 C 0.13889(19) 0.67656(10) 0.75420(18) 0.0244(3) Uani 1 1 d . . . . . H9 H 0.041746 0.677238 0.700065 0.029 Uiso 1 1 calc R U . . . C10 C 0.3457(2) 0.71736(11) 0.8930(2) 0.0335(4) Uani 1 1 d . . . . . H10 H 0.416068 0.751185 0.951307 0.040 Uiso 1 1 calc R U . . . C11 C 0.3674(2) 0.63667(11) 0.8561(2) 0.0320(4) Uani 1 1 d . . . . . H11 H 0.454249 0.604408 0.884497 0.038 Uiso 1 1 calc R U . . . C12 C 0.1437(2) 0.82418(11) 0.8378(2) 0.0342(4) Uani 1 1 d . . . . . H12A H 0.168168 0.846356 0.938240 0.041 Uiso 1 1 calc R U . . . H12B H 0.033567 0.821080 0.815410 0.041 Uiso 1 1 calc R U . . . C13 C 0.2026(3) 0.88220(12) 0.7317(2) 0.0459(5) Uani 1 1 d . . . . . H13A H 0.174139 0.862020 0.631622 0.069 Uiso 1 1 calc R U . . . H13B H 0.311703 0.885057 0.752764 0.069 Uiso 1 1 calc R U . . . H13C H 0.160216 0.937333 0.741384 0.069 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 0.0276(2) 0.0214(2) 0.0249(2) -0.00556(14) 0.00278(16) -0.00276(13) O1 0.0347(7) 0.0221(6) 0.0302(6) -0.0060(5) 0.0001(5) 0.0072(5) O2 0.0303(7) 0.0304(6) 0.0304(6) -0.0059(5) -0.0010(5) -0.0039(5) O3 0.0382(7) 0.0361(7) 0.0367(7) -0.0148(5) 0.0147(6) -0.0087(5) N1 0.0350(8) 0.0182(7) 0.0263(7) -0.0025(5) 0.0084(6) -0.0039(5) N2 0.0357(8) 0.0169(6) 0.0285(7) -0.0048(5) 0.0048(6) -0.0019(5) C1 0.0296(8) 0.0190(7) 0.0267(8) -0.0024(6) -0.0031(6) 0.0008(6) C2 0.0253(8) 0.0175(7) 0.0246(8) 0.0001(6) 0.0001(6) -0.0012(6) C3 0.0370(9) 0.0241(8) 0.0296(9) 0.0003(7) 0.0062(7) -0.0009(7) C4 0.0496(11) 0.0336(10) 0.0294(9) 0.0056(7) 0.0056(8) -0.0051(8) C5 0.0629(13) 0.0246(9) 0.0337(10) 0.0089(7) -0.0060(9) -0.0026(9) C6 0.0491(11) 0.0195(8) 0.0338(10) 0.0009(7) -0.0094(8) 0.0038(7) C7 0.0251(8) 0.0168(7) 0.0234(7) -0.0011(6) 0.0020(6) 0.0002(6) C8 0.0299(8) 0.0162(7) 0.0239(8) -0.0005(6) 0.0042(6) -0.0021(6) C9 0.0299(8) 0.0188(7) 0.0248(8) -0.0023(6) 0.0041(6) -0.0022(6) C10 0.0384(10) 0.0239(8) 0.0357(10) -0.0046(7) -0.0042(8) -0.0061(7) C11 0.0338(9) 0.0225(8) 0.0375(10) -0.0022(7) -0.0038(8) -0.0011(7) C12 0.0430(10) 0.0198(8) 0.0404(10) -0.0091(7) 0.0085(8) 0.0022(7) C13 0.0733(15) 0.0261(9) 0.0382(11) 0.0055(8) 0.0066(10) 0.0111(9) 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 O1 S1 N1 104.02(7) . . ? O2 S1 O1 107.74(8) . . ? O2 S1 O3 119.81(8) . . ? O2 S1 N1 109.00(8) . . ? O3 S1 O1 104.32(8) . . ? O3 S1 N1 110.67(8) . . ? C1 O1 S1 116.17(10) . . ? S1 N1 H1 122.8 . . ? C7 N1 S1 114.47(10) . . ? C7 N1 H1 122.8 . . ? C9 N2 C12 125.10(16) . . ? C10 N2 C9 108.99(14) . . ? C10 N2 C12 125.69(15) . . ? C2 C1 O1 121.87(15) . . ? C6 C1 O1 115.39(15) . . ? C6 C1 C2 122.73(17) . . ? C1 C2 C7 123.60(15) . . ? C3 C2 C1 116.69(15) . . ? C3 C2 C7 119.58(14) . . ? C2 C3 H3 119.1 . . ? C4 C3 C2 121.80(17) . . ? C4 C3 H3 119.1 . . ? C3 C4 H4 120.2 . . ? C3 C4 C5 119.61(19) . . ? C5 C4 H4 120.2 . . ? C4 C5 H5 119.8 . . ? C6 C5 C4 120.32(17) . . ? C6 C5 H5 119.8 . . ? C1 C6 H6 120.6 . . ? C5 C6 C1 118.83(17) . . ? C5 C6 H6 120.6 . . ? N1 C7 C2 110.81(13) . . ? N1 C7 H7 107.6 . . ? N1 C7 C8 108.68(12) . . ? C2 C7 H7 107.6 . . ? C8 C7 C2 114.17(13) . . ? C8 C7 H7 107.6 . . ? C9 C8 C7 125.09(15) . . ? C9 C8 C11 107.02(14) . . ? C11 C8 C7 127.89(15) . . ? N2 C9 C8 108.43(15) . . ? N2 C9 H9 125.8 . . ? C8 C9 H9 125.8 . . ? N2 C10 H10 125.7 . . ? N2 C10 C11 108.68(16) . . ? C11 C10 H10 125.7 . . ? C8 C11 H11 126.6 . . ? C10 C11 C8 106.87(16) . . ? C10 C11 H11 126.6 . . ? N2 C12 H12A 109.1 . . ? N2 C12 H12B 109.1 . . ? N2 C12 C13 112.30(16) . . ? H12A C12 H12B 107.9 . . ? C13 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 1.5931(13) . ? S1 O2 1.4197(13) . ? S1 O3 1.4208(13) . ? S1 N1 1.5994(14) . ? O1 C1 1.416(2) . ? N1 H1 0.8800 . ? N1 C7 1.494(2) . ? N2 C9 1.364(2) . ? N2 C10 1.363(2) . ? N2 C12 1.465(2) . ? C1 C2 1.393(2) . ? C1 C6 1.386(2) . ? C2 C3 1.393(2) . ? C2 C7 1.522(2) . ? C3 H3 0.9500 . ? C3 C4 1.387(3) . ? C4 H4 0.9500 . ? C4 C5 1.387(3) . ? C5 H5 0.9500 . ? C5 C6 1.382(3) . ? C6 H6 0.9500 . ? C7 H7 1.0000 . ? C7 C8 1.495(2) . ? C8 C9 1.373(2) . ? C8 C11 1.420(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C10 C11 1.371(2) . ? C11 H11 0.9500 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.504(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 O1 C1 C2 -24.7(2) . . . . ? S1 O1 C1 C6 156.59(13) . . . . ? S1 N1 C7 C2 45.54(16) . . . . ? S1 N1 C7 C8 171.76(11) . . . . ? O1 S1 N1 C7 -60.11(13) . . . . ? O1 C1 C2 C3 -177.36(15) . . . . ? O1 C1 C2 C7 6.8(2) . . . . ? O1 C1 C6 C5 178.18(17) . . . . ? O2 S1 O1 C1 -67.60(13) . . . . ? O2 S1 N1 C7 54.61(14) . . . . ? O3 S1 O1 C1 164.06(11) . . . . ? O3 S1 N1 C7 -171.62(12) . . . . ? N1 S1 O1 C1 48.01(13) . . . . ? N1 C7 C8 C9 108.58(18) . . . . ? N1 C7 C8 C11 -70.8(2) . . . . ? N2 C10 C11 C8 0.6(2) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C1 C2 C7 N1 -17.0(2) . . . . ? C1 C2 C7 C8 -140.12(16) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C2 C7 C8 C9 -127.16(17) . . . . ? C2 C7 C8 C11 53.5(2) . . . . ? C3 C2 C7 N1 167.28(15) . . . . ? C3 C2 C7 C8 44.2(2) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C6 C1 C2 C3 1.3(3) . . . . ? C6 C1 C2 C7 -174.53(16) . . . . ? C7 C2 C3 C4 174.85(17) . . . . ? C7 C8 C9 N2 179.99(15) . . . . ? C7 C8 C11 C10 179.38(17) . . . . ? C9 N2 C10 C11 -1.0(2) . . . . ? C9 N2 C12 C13 -96.7(2) . . . . ? C9 C8 C11 C10 -0.1(2) . . . . ? C10 N2 C9 C8 1.0(2) . . . . ? C10 N2 C12 C13 77.3(2) . . . . ? C11 C8 C9 N2 -0.6(2) . . . . ? C12 N2 C9 C8 175.83(16) . . . . ? C12 N2 C10 C11 -175.83(17) . . . . ?