#------------------------------------------------------------------------------ #$Date: 2020-05-06 23:28:26 +0300 (Wed, 06 May 2020) $ #$Revision: 251823 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/80/1558022.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_1558022 loop_ _publ_author_name 'Wu, Xiao-Yun' 'Gui, Hou-Ze' 'Jangra, Harish' 'Wei, Yin' 'Shi, Min' 'Zipse, Hendrik' _publ_section_title ; Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with allenoates and mechanistic studies ; _journal_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/D0CY00092B _journal_year 2020 _chemical_formula_moiety 'C15 H19 N O6 S' _chemical_formula_sum 'C15 H19 N O6 S' _chemical_formula_weight 341.37 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-07-01 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-07-04 deposited with the CCDC. 2020-05-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 13.3705(2) _cell_length_b 7.27390(10) _cell_length_c 31.8622(5) _cell_measurement_reflns_used 9963 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 54.93 _cell_measurement_theta_min 5.63 _cell_volume 3098.78(8) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 170.02 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 30140 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.938 _diffrn_reflns_theta_min 5.625 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.393 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.5930 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0941 before and 0.0493 after correction. The Ratio of minimum to maximum transmission is 0.7898. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.463 _exptl_crystal_description block _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.273 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2913 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0331 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.7663P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.0877 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2733 _reflns_number_total 2913 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cy00092b3.cif _cod_data_source_block mj19431 _cod_database_code 1558022 _shelx_shelxl_version_number 2016/6 _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 0.921 _shelx_estimated_absorpt_t_min 0.851 _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, All O(H) groups 2.a Ternary CH refined with riding coordinates: C2(H2) 2.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C4(H4A,H4B) 2.c Aromatic/amide H refined with riding coordinates: C10(H10), C11(H11), C13(H13), C14(H14) 2.d Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C) 2.e Idealised tetrahedral OH refined as rotating group: O4(H4) ; _shelx_res_file ; TITL mj19431_a.res in Pbca mj19431.res created by SHELXL-2016/6 at 15:49:48 on 01-Jul-2019 REM Old TITL mj19431 in Pbca REM SHELXT solution in Pbca REM R1 0.115, Rweak 0.002, Alpha 0.025, Orientation as input REM Formula found by SHELXT: C15 N O6 S CELL 1.34139 13.3705 7.2739 31.8622 90 90 90 ZERR 8 0.0002 0.0001 0.0005 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O S DISP C 0.0148 0.007 57.7477 DISP H -0 0 0.6481 DISP N 0.0253 0.0136 110.5121 DISP O 0.0412 0.025 193.9543 DISP S 0.2924 0.4247 3241.7632 UNIT 120 152 8 48 8 L.S. 4 PLAN 20 SIZE 0.06 0.08 0.12 TEMP -103.13 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.041100 1.766300 FVAR 0.56828 S1 5 0.445851 0.753751 0.358943 11.00000 0.02648 0.02211 = 0.02650 0.00463 -0.00418 -0.00149 O1 4 0.581752 0.610460 0.450498 11.00000 0.02818 0.03276 = 0.02883 -0.00383 -0.00448 -0.00290 O2 4 0.662938 0.419097 0.406845 11.00000 0.01577 0.02818 = 0.03543 0.00341 -0.00095 0.00005 O3 4 0.548412 0.170678 0.468626 11.00000 0.01907 0.03431 = 0.03750 0.01421 0.00043 -0.00062 O4 4 0.390259 0.072254 0.474071 11.00000 0.02182 0.03469 = 0.03526 0.01509 -0.00247 -0.00656 AFIX 147 H4 2 0.415381 0.000434 0.491821 11.00000 -1.50000 AFIX 0 O5 4 0.552195 0.761675 0.353541 11.00000 0.02726 0.03942 = 0.03506 0.00959 -0.00404 -0.01001 O6 4 0.391605 0.914894 0.371430 11.00000 0.04795 0.02284 = 0.03896 0.00103 -0.00638 0.00523 N1 3 0.421354 0.597618 0.393280 11.00000 0.01983 0.02474 = 0.02418 0.00491 0.00063 0.00439 C1 1 0.485282 0.433230 0.400573 11.00000 0.01775 0.02089 = 0.02164 0.00275 -0.00009 0.00164 C2 1 0.415557 0.324239 0.430566 11.00000 0.01659 0.02606 = 0.02298 0.00323 -0.00066 -0.00243 AFIX 13 H2 2 0.365531 0.259292 0.412552 11.00000 -1.20000 AFIX 0 C3 1 0.358324 0.471380 0.455153 11.00000 0.02136 0.03438 = 0.02591 0.00285 0.00429 0.00256 AFIX 23 H3A 2 0.296688 0.420468 0.467855 11.00000 -1.20000 H3B 2 0.400401 0.525896 0.477486 11.00000 -1.20000 AFIX 0 C4 1 0.334190 0.610730 0.421414 11.00000 0.02356 0.03519 = 0.03279 0.00424 0.00533 0.00912 AFIX 23 H4A 2 0.271600 0.578485 0.406535 11.00000 -1.20000 H4B 2 0.327734 0.735849 0.433338 11.00000 -1.20000 AFIX 0 C5 1 0.460271 0.181910 0.459281 11.00000 0.01941 0.02493 = 0.02309 0.00200 0.00278 -0.00182 C6 1 0.581563 0.498734 0.422721 11.00000 0.01917 0.02182 = 0.02392 0.00608 -0.00021 -0.00071 C7 1 0.756978 0.467735 0.426526 11.00000 0.01738 0.03434 = 0.06117 0.00415 -0.00925 -0.00121 AFIX 137 H7A 2 0.811686 0.401622 0.412700 11.00000 -1.50000 H7B 2 0.754913 0.434032 0.456293 11.00000 -1.50000 H7C 2 0.767941 0.600450 0.423898 11.00000 -1.50000 AFIX 0 C8 1 0.505811 0.323654 0.360764 11.00000 0.02525 0.02648 = 0.02530 -0.00211 0.00089 -0.00115 AFIX 137 H8A 2 0.442435 0.296107 0.346650 11.00000 -1.50000 H8B 2 0.539669 0.208501 0.368048 11.00000 -1.50000 H8C 2 0.548539 0.395845 0.341978 11.00000 -1.50000 AFIX 0 C9 1 0.393959 0.681180 0.310723 11.00000 0.02779 0.02434 = 0.02518 0.00571 -0.00348 0.00201 C10 1 0.454055 0.660648 0.275763 11.00000 0.02863 0.04133 = 0.03033 0.00792 0.00055 0.00083 AFIX 43 H10 2 0.524036 0.681582 0.277704 11.00000 -1.20000 AFIX 0 C11 1 0.411729 0.609440 0.237929 11.00000 0.03932 0.04188 = 0.02587 0.00506 0.00176 0.00586 AFIX 43 H11 2 0.453407 0.595359 0.213997 11.00000 -1.20000 AFIX 0 C12 1 0.309645 0.578125 0.234128 11.00000 0.04276 0.02367 = 0.02993 0.00261 -0.00704 0.00403 C13 1 0.251060 0.595420 0.269868 11.00000 0.03081 0.05175 = 0.03841 -0.00034 -0.00659 -0.00400 AFIX 43 H13 2 0.181400 0.570803 0.268163 11.00000 -1.20000 AFIX 0 C14 1 0.291985 0.647797 0.307960 11.00000 0.02844 0.05499 = 0.03015 -0.00091 -0.00099 -0.00058 AFIX 43 H14 2 0.250581 0.660773 0.332008 11.00000 -1.20000 AFIX 0 C15 1 0.264291 0.525552 0.192616 11.00000 0.05869 0.03506 = 0.03513 -0.00442 -0.01319 0.00452 AFIX 137 H15A 2 0.247476 0.636986 0.176834 11.00000 -1.50000 H15B 2 0.203492 0.453309 0.197420 11.00000 -1.50000 H15C 2 0.312363 0.452115 0.176553 11.00000 -1.50000 AFIX 0 HKLF 4 REM mj19431_a.res in Pbca REM R1 = 0.0331 for 2733 Fo > 4sig(Fo) and 0.0351 for all 2913 data REM 212 parameters refined using 0 restraints END WGHT 0.0411 1.7663 REM Highest difference peak 0.273, deepest hole -0.387, 1-sigma level 0.041 Q1 1 0.1966 0.5892 0.1898 11.00000 0.05 0.27 Q2 1 0.4534 0.3783 0.4166 11.00000 0.05 0.27 Q3 1 0.4174 0.7121 0.3300 11.00000 0.05 0.26 Q4 1 0.5346 0.4610 0.4117 11.00000 0.05 0.24 Q5 1 0.4411 0.2565 0.4426 11.00000 0.05 0.23 Q6 1 0.4015 0.3971 0.4458 11.00000 0.05 0.23 Q7 1 0.4971 0.3805 0.3815 11.00000 0.05 0.23 Q8 1 0.3032 0.5916 0.1688 11.00000 0.05 0.22 Q9 1 0.2703 0.6846 0.2602 11.00000 0.05 0.21 Q10 1 0.4557 0.5270 0.3969 11.00000 0.05 0.20 Q11 1 0.4284 0.6510 0.3798 11.00000 0.05 0.20 Q12 1 0.3161 0.7432 0.3018 11.00000 0.05 0.19 Q13 1 0.3535 0.6415 0.2335 11.00000 0.05 0.19 Q14 1 0.4228 0.7026 0.2942 11.00000 0.05 0.18 Q15 1 0.7444 0.5704 0.4496 11.00000 0.05 0.17 Q16 1 0.3425 0.7209 0.3064 11.00000 0.05 0.16 Q17 1 0.3398 0.5421 0.4391 11.00000 0.05 0.16 Q18 1 0.2923 0.5579 0.2140 11.00000 0.05 0.16 Q19 1 0.3816 0.5931 0.4033 11.00000 0.05 0.16 Q20 1 0.2638 0.3903 0.1858 11.00000 0.05 0.15 ; _shelx_res_checksum 83704 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, 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 S1 S 0.44585(3) 0.75375(5) 0.35894(2) 0.02503(13) Uani 1 1 d . . . . . O1 O 0.58175(8) 0.61046(15) 0.45050(3) 0.0299(3) Uani 1 1 d . . . . . O2 O 0.66294(7) 0.41910(14) 0.40684(3) 0.0265(2) Uani 1 1 d . . . . . O3 O 0.54841(7) 0.17068(16) 0.46863(3) 0.0303(3) Uani 1 1 d . . . . . O4 O 0.39026(8) 0.07225(15) 0.47407(3) 0.0306(3) Uani 1 1 d . . . . . H4 H 0.415381 0.000434 0.491821 0.046 Uiso 1 1 calc GR . . . . O5 O 0.55220(8) 0.76168(16) 0.35354(4) 0.0339(3) Uani 1 1 d . . . . . O6 O 0.39161(9) 0.91489(15) 0.37143(4) 0.0366(3) Uani 1 1 d . . . . . N1 N 0.42135(9) 0.59762(17) 0.39328(4) 0.0229(3) Uani 1 1 d . . . . . C1 C 0.48528(10) 0.43323(19) 0.40057(4) 0.0201(3) Uani 1 1 d . . . . . C2 C 0.41556(10) 0.3242(2) 0.43057(4) 0.0219(3) Uani 1 1 d . . . . . H2 H 0.365531 0.259292 0.412552 0.026 Uiso 1 1 calc R . . . . C3 C 0.35832(11) 0.4714(2) 0.45515(5) 0.0272(3) Uani 1 1 d . . . . . H3A H 0.296688 0.420468 0.467855 0.033 Uiso 1 1 calc R . . . . H3B H 0.400401 0.525896 0.477486 0.033 Uiso 1 1 calc R . . . . C4 C 0.33419(11) 0.6107(2) 0.42141(5) 0.0305(4) Uani 1 1 d . . . . . H4A H 0.271600 0.578485 0.406535 0.037 Uiso 1 1 calc R . . . . H4B H 0.327734 0.735849 0.433338 0.037 Uiso 1 1 calc R . . . . C5 C 0.46027(10) 0.1819(2) 0.45928(4) 0.0225(3) Uani 1 1 d . . . . . C6 C 0.58156(10) 0.4987(2) 0.42272(4) 0.0216(3) Uani 1 1 d . . . . . C7 C 0.75698(11) 0.4677(2) 0.42653(6) 0.0376(4) Uani 1 1 d . . . . . H7A H 0.811686 0.401622 0.412700 0.056 Uiso 1 1 calc GR . . . . H7B H 0.754913 0.434032 0.456293 0.056 Uiso 1 1 calc GR . . . . H7C H 0.767941 0.600450 0.423898 0.056 Uiso 1 1 calc GR . . . . C8 C 0.50581(11) 0.3237(2) 0.36076(5) 0.0257(3) Uani 1 1 d . . . . . H8A H 0.442435 0.296107 0.346650 0.039 Uiso 1 1 calc GR . . . . H8B H 0.539669 0.208501 0.368048 0.039 Uiso 1 1 calc GR . . . . H8C H 0.548539 0.395845 0.341978 0.039 Uiso 1 1 calc GR . . . . C9 C 0.39396(11) 0.6812(2) 0.31072(4) 0.0258(3) Uani 1 1 d . . . . . C10 C 0.45406(12) 0.6606(2) 0.27576(5) 0.0334(4) Uani 1 1 d . . . . . H10 H 0.524036 0.681582 0.277704 0.040 Uiso 1 1 calc R . . . . C11 C 0.41173(13) 0.6094(2) 0.23793(5) 0.0357(4) Uani 1 1 d . . . . . H11 H 0.453407 0.595359 0.213997 0.043 Uiso 1 1 calc R . . . . C12 C 0.30965(13) 0.5781(2) 0.23413(5) 0.0321(4) Uani 1 1 d . . . . . C13 C 0.25106(14) 0.5954(3) 0.26987(5) 0.0403(4) Uani 1 1 d . . . . . H13 H 0.181400 0.570803 0.268163 0.048 Uiso 1 1 calc R . . . . C14 C 0.29199(12) 0.6478(3) 0.30796(5) 0.0379(4) Uani 1 1 d . . . . . H14 H 0.250581 0.660773 0.332008 0.045 Uiso 1 1 calc R . . . . C15 C 0.26429(15) 0.5256(3) 0.19262(5) 0.0430(4) Uani 1 1 d . . . . . H15A H 0.247476 0.636986 0.176834 0.064 Uiso 1 1 calc GR . . . . H15B H 0.203492 0.453309 0.197420 0.064 Uiso 1 1 calc GR . . . . H15C H 0.312363 0.452115 0.176553 0.064 Uiso 1 1 calc GR . . . . 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 0.0265(2) 0.0221(2) 0.0265(2) 0.00463(13) -0.00418(14) -0.00149(14) O1 0.0282(6) 0.0328(6) 0.0288(5) -0.0038(5) -0.0045(4) -0.0029(5) O2 0.0158(5) 0.0282(5) 0.0354(6) 0.0034(4) -0.0010(4) 0.0000(4) O3 0.0191(5) 0.0343(6) 0.0375(6) 0.0142(5) 0.0004(4) -0.0006(4) O4 0.0218(5) 0.0347(6) 0.0353(6) 0.0151(5) -0.0025(4) -0.0066(5) O5 0.0273(6) 0.0394(7) 0.0351(6) 0.0096(5) -0.0040(5) -0.0100(5) O6 0.0480(7) 0.0228(6) 0.0390(6) 0.0010(5) -0.0064(5) 0.0052(5) N1 0.0198(6) 0.0247(6) 0.0242(6) 0.0049(5) 0.0006(5) 0.0044(5) C1 0.0177(7) 0.0209(7) 0.0216(6) 0.0027(5) -0.0001(5) 0.0016(5) C2 0.0166(6) 0.0261(7) 0.0230(7) 0.0032(6) -0.0007(5) -0.0024(6) C3 0.0214(7) 0.0344(8) 0.0259(7) 0.0029(6) 0.0043(6) 0.0026(6) C4 0.0236(7) 0.0352(8) 0.0328(8) 0.0042(7) 0.0053(6) 0.0091(6) C5 0.0194(7) 0.0249(7) 0.0231(7) 0.0020(6) 0.0028(5) -0.0018(6) C6 0.0192(7) 0.0218(7) 0.0239(7) 0.0061(6) -0.0002(5) -0.0007(5) C7 0.0174(7) 0.0343(9) 0.0612(11) 0.0042(8) -0.0093(7) -0.0012(6) C8 0.0253(8) 0.0265(8) 0.0253(7) -0.0021(6) 0.0009(6) -0.0012(6) C9 0.0278(8) 0.0243(7) 0.0252(7) 0.0057(6) -0.0035(6) 0.0020(6) C10 0.0286(8) 0.0413(9) 0.0303(8) 0.0079(7) 0.0005(6) 0.0008(7) C11 0.0393(9) 0.0419(9) 0.0259(8) 0.0051(7) 0.0018(7) 0.0059(8) C12 0.0428(9) 0.0237(7) 0.0299(8) 0.0026(6) -0.0070(7) 0.0040(7) C13 0.0308(8) 0.0517(11) 0.0384(9) -0.0003(8) -0.0066(7) -0.0040(8) C14 0.0284(8) 0.0550(11) 0.0301(8) -0.0009(8) -0.0010(7) -0.0006(8) C15 0.0587(12) 0.0351(9) 0.0351(9) -0.0044(7) -0.0132(8) 0.0045(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2924 0.4247 '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 O5 S1 O6 120.13(7) . . ? O5 S1 N1 108.16(7) . . ? O5 S1 C9 107.29(7) . . ? O6 S1 N1 106.55(7) . . ? O6 S1 C9 106.67(7) . . ? N1 S1 C9 107.47(7) . . ? C6 O2 C7 115.99(12) . . ? C5 O4 H4 109.5 . . ? C1 N1 S1 123.77(9) . . ? C4 N1 S1 121.90(10) . . ? C4 N1 C1 114.29(11) . . ? N1 C1 C2 99.29(11) . . ? N1 C1 C6 107.60(11) . . ? N1 C1 C8 113.20(11) . . ? C6 C1 C2 112.15(11) . . ? C8 C1 C2 110.71(12) . . ? C8 C1 C6 113.08(11) . . ? C1 C2 H2 106.8 . . ? C3 C2 C1 104.95(12) . . ? C3 C2 H2 106.8 . . ? C5 C2 C1 119.13(11) . . ? C5 C2 H2 106.8 . . ? C5 C2 C3 111.60(12) . . ? C2 C3 H3A 111.3 . . ? C2 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C4 C3 C2 102.21(12) . . ? C4 C3 H3A 111.3 . . ? C4 C3 H3B 111.3 . . ? N1 C4 C3 102.73(11) . . ? N1 C4 H4A 111.2 . . ? N1 C4 H4B 111.2 . . ? C3 C4 H4A 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? O3 C5 O4 124.02(13) . . ? O3 C5 C2 125.37(13) . . ? O4 C5 C2 110.59(12) . . ? O1 C6 O2 124.89(13) . . ? O1 C6 C1 123.18(13) . . ? O2 C6 C1 111.92(12) . . ? O2 C7 H7A 109.5 . . ? O2 C7 H7B 109.5 . . ? O2 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 S1 120.34(12) . . ? C10 C9 C14 120.09(15) . . ? C14 C9 S1 119.56(12) . . ? C9 C10 H10 120.2 . . ? C9 C10 C11 119.60(15) . . ? C11 C10 H10 120.2 . . ? C10 C11 H11 119.3 . . ? C10 C11 C12 121.49(15) . . ? C12 C11 H11 119.3 . . ? C11 C12 C15 120.96(16) . . ? C13 C12 C11 117.92(15) . . ? C13 C12 C15 121.12(16) . . ? C12 C13 H13 119.3 . . ? C14 C13 C12 121.40(16) . . ? C14 C13 H13 119.3 . . ? C9 C14 H14 120.3 . . ? C13 C14 C9 119.47(16) . . ? C13 C14 H14 120.3 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 O5 1.4334(12) . ? S1 O6 1.4347(12) . ? S1 N1 1.6106(12) . ? S1 C9 1.7665(15) . ? O1 C6 1.2016(18) . ? O2 C6 1.3324(17) . ? O2 C7 1.4489(18) . ? O3 C5 1.2183(18) . ? O4 H4 0.8400 . ? O4 C5 1.3170(17) . ? N1 C1 1.4881(17) . ? N1 C4 1.4734(18) . ? C1 C2 1.5527(19) . ? C1 C6 1.5434(19) . ? C1 C8 1.5230(19) . ? C2 H2 1.0000 . ? C2 C3 1.531(2) . ? C2 C5 1.505(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.512(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.382(2) . ? C9 C14 1.388(2) . ? C10 H10 0.9500 . ? C10 C11 1.383(2) . ? C11 H11 0.9500 . ? C11 C12 1.389(2) . ? C12 C13 1.388(2) . ? C12 C15 1.504(2) . ? C13 H13 0.9500 . ? C13 C14 1.385(2) . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ?