#------------------------------------------------------------------------------ #$Date: 2019-05-18 04:09:11 +0300 (Sat, 18 May 2019) $ #$Revision: 215288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123489.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_7123489 loop_ _publ_author_name 'Gharpure, Santosh J.' 'Vishwakarma, Dharmendra S.' 'Patel, Raj Kumar' _publ_section_title ; TMSOTf Mediated ‘5/6-endo-dig’ Reductive Hydroamination for the Stereoselective Synthesis of Pyrrolidine and Piperidine derivatives ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC03127H _journal_year 2019 _chemical_absolute_configuration unk _chemical_formula_moiety 'C19 H23 N O2 S' _chemical_formula_sum 'C19 H23 N O2 S' _chemical_formula_weight 329.44 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-10-18 _audit_creation_method ; Olex2 1.2-ac3 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2019-04-02 deposited with the CCDC. 2019-05-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6838(3) _cell_length_b 11.6378(7) _cell_length_c 19.1666(13) _cell_measurement_reflns_used 5820 _cell_measurement_temperature 150 _cell_measurement_theta_max 31.0500 _cell_measurement_theta_min 2.0800 _cell_volume 1713.93(17) _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_collection 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _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 150 _diffrn_detector CCD _diffrn_detector_area_resol_mean 28.5714 _diffrn_detector_type 'Rigaku Saturn724+' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -75.50 19.00 0.50 8.00 -- -20.00 -72.00 36.00 189 2 \w -90.00 0.00 0.50 8.00 -- -20.00 -72.00-108.00 180 3 \w -30.00 0.00 0.50 8.00 -- -20.00 0.00-180.00 60 4 \w -96.50 -70.50 0.50 8.00 -- -20.00 -72.00 -36.00 52 ; _diffrn_measurement_device 'AFC12 (Right): Kappa 3 circle' _diffrn_measurement_device_type 'Rigaku Saturn724+ (2x2 bin mode)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'Mitegen 50um' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0295014000 _diffrn_orient_matrix_UB_12 0.0199231000 _diffrn_orient_matrix_UB_13 -0.0329338000 _diffrn_orient_matrix_UB_21 0.0870950000 _diffrn_orient_matrix_UB_22 0.0013608000 _diffrn_orient_matrix_UB_23 -0.0122672000 _diffrn_orient_matrix_UB_31 -0.0081513000 _diffrn_orient_matrix_UB_32 -0.0575574000 _diffrn_orient_matrix_UB_33 -0.0116362000 _diffrn_radiation_collimation 0.3 _diffrn_radiation_monochromator Confocal _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_unetI/netI 0.0458 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7840 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 24.993 _diffrn_reflns_theta_max 24.993 _diffrn_reflns_theta_min 2.047 _diffrn_source 'Rotating Anode' _diffrn_source_current 24.0 _diffrn_source_power 1.2 _diffrn_source_target Mo _diffrn_source_type 'Rotating Anode' _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88590 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 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 1.277 _exptl_crystal_description block _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.208 _exptl_crystal_size_mid 0.156 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.399 _refine_diff_density_min -0.735 _refine_diff_density_rms 0.181 _refine_ls_abs_structure_details ; Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2964 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.210 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0438 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0804P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1177 _refine_ls_wR_factor_ref 0.1412 _reflns_Friedel_coverage 0.693 _reflns_Friedel_fraction_full 0.959 _reflns_Friedel_fraction_max 0.959 _reflns_number_gt 2709 _reflns_number_total 2964 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc03127h2.cif _cod_data_source_block sjg-rp-03-191-p_mo _cod_original_cell_volume 1713.92(16) _cod_database_code 7123489 _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_max 0.990 _shelx_estimated_absorpt_t_min 0.960 _reflns_odcompleteness_completeness 92.99 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.09 _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 Ternary CH refined with riding coordinates: C18(H18), C8(H8) 2.b Secondary CH2 refined with riding coordinates: C17(H17A,H17B), C15(H15A,H15B), C16(H16A,H16B) 2.c Aromatic/amide H refined with riding coordinates: C10(H10), C7(H7), C4(H4), C6(H6), C11(H11), C14(H14), C3(H3), C12(H12), C13(H13) 2.d Idealised Me refined as rotating group: C19(H19A,H19B,H19C), C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL sjg-rp-03-191-p_mo_a.res in P2(1)2(1)2(1) sjg-rp-03-191-p_mo.res created by SHELXL-2018/3 at 16:06:26 on 18-Oct-2018 REM Old TITL sjg-rp-03-191-p_mo_a.res in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.128, Rweak 0.030, Alpha 0.001, Orientation as input REM Flack x = 0.146 ( 0.049 ) from Parsons' quotients REM Formula found by SHELXT: C19 N O2 Cl CELL 0.71073 7.683804 11.637796 19.166567 90 90 90 ZERR 4 0.000297 0.000661 0.00128 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 UNIT 76 92 4 8 4 L.S. 100 PLAN 20 SIZE 0.05 0.156 0.208 TEMP -123.15 BOND $H list 4 fmap 2 acta OMIT -3 50 REM REM REM WGHT 0.080400 FVAR 3.97651 S1 5 0.545270 0.635871 0.225625 11.00000 0.01943 0.02983 = 0.03027 -0.00693 0.00150 -0.00811 O1 4 0.568793 0.516992 0.209032 11.00000 0.04032 0.02891 = 0.05006 -0.01696 0.01116 -0.01636 O2 4 0.404629 0.698082 0.194825 11.00000 0.01841 0.05647 = 0.03353 -0.00345 -0.00420 -0.00444 N1 3 0.722891 0.701672 0.204424 11.00000 0.01708 0.01891 = 0.02853 -0.00070 0.00131 0.00005 C18 1 0.892130 0.643987 0.218912 11.00000 0.01901 0.01820 = 0.02545 -0.00070 0.00028 0.00124 AFIX 13 H18 2 0.865620 0.564965 0.236432 11.00000 -1.20000 AFIX 0 C10 1 0.714014 0.798226 0.065443 11.00000 0.04262 0.03513 = 0.02986 -0.00160 -0.01502 0.00654 AFIX 43 H10 2 0.637346 0.735585 0.073528 11.00000 -1.20000 AFIX 0 C5 1 0.519903 0.644856 0.316747 11.00000 0.01821 0.02596 = 0.02882 -0.00179 0.00175 -0.00827 C17 1 0.991305 0.706470 0.276197 11.00000 0.02206 0.02274 = 0.02545 0.00024 -0.00021 0.00039 AFIX 23 H17A 2 1.109795 0.673591 0.279789 11.00000 -1.20000 H17B 2 0.931725 0.693533 0.321316 11.00000 -1.20000 AFIX 0 C7 1 0.422679 0.750683 0.416678 11.00000 0.02943 0.03511 = 0.03433 -0.00679 0.00193 -0.00378 AFIX 43 H7 2 0.371344 0.817805 0.435969 11.00000 -1.20000 AFIX 0 C4 1 0.576300 0.556807 0.360397 11.00000 0.02721 0.02293 = 0.04259 0.00029 0.00115 -0.00434 AFIX 43 H4 2 0.631210 0.490823 0.341242 11.00000 -1.20000 AFIX 0 C15 1 0.823869 0.885447 0.254386 11.00000 0.03009 0.01807 = 0.02338 0.00028 0.00232 -0.00200 AFIX 23 H15A 2 0.833675 0.968739 0.244650 11.00000 -1.20000 H15B 2 0.758983 0.876252 0.298659 11.00000 -1.20000 AFIX 0 C19 1 0.995576 0.630969 0.151650 11.00000 0.02621 0.02651 = 0.02810 -0.00101 0.00323 0.00750 AFIX 137 H19A 2 0.924673 0.590729 0.116873 11.00000 -1.50000 H19B 2 1.101556 0.586657 0.160885 11.00000 -1.50000 H19C 2 1.027102 0.707138 0.133885 11.00000 -1.50000 AFIX 0 C9 1 0.778910 0.860115 0.121838 11.00000 0.02990 0.02096 = 0.02719 0.00205 -0.00372 0.00871 C8 1 0.721396 0.828374 0.195576 11.00000 0.02052 0.01954 = 0.02810 -0.00328 -0.00225 0.00123 AFIX 13 H8 2 0.597719 0.853854 0.200518 11.00000 -1.20000 AFIX 0 C6 1 0.444319 0.743001 0.345570 11.00000 0.02629 0.02827 = 0.02629 -0.00112 0.00028 -0.00261 AFIX 43 H6 2 0.407960 0.804250 0.316224 11.00000 -1.20000 AFIX 0 C2 1 0.474634 0.661786 0.461195 11.00000 0.03023 0.04117 = 0.03108 -0.00009 -0.00261 -0.00847 C11 1 0.759446 0.826545 -0.002132 11.00000 0.06765 0.05225 = 0.03089 -0.00689 -0.02219 0.02033 AFIX 43 H11 2 0.714072 0.782822 -0.039829 11.00000 -1.20000 AFIX 0 C16 1 1.005465 0.835373 0.263134 11.00000 0.02400 0.02346 = 0.02806 -0.00174 -0.00455 -0.00557 AFIX 23 H16A 2 1.064867 0.872802 0.302938 11.00000 -1.20000 H16B 2 1.074939 0.849662 0.220508 11.00000 -1.20000 AFIX 0 C14 1 0.889426 0.951537 0.107209 11.00000 0.04393 0.02872 = 0.03067 0.00089 0.00053 0.00071 AFIX 43 H14 2 0.935428 0.995707 0.144590 11.00000 -1.20000 AFIX 0 C3 1 0.552309 0.565555 0.431480 11.00000 0.03383 0.02876 = 0.04246 0.01210 -0.00331 -0.00711 AFIX 43 H3 2 0.589637 0.504535 0.460806 11.00000 -1.20000 AFIX 0 C12 1 0.869641 0.917300 -0.015680 11.00000 0.07446 0.05299 = 0.02959 0.01539 0.00617 0.02894 AFIX 43 H12 2 0.900611 0.936431 -0.062238 11.00000 -1.20000 AFIX 0 C13 1 0.933747 0.979508 0.039543 11.00000 0.06341 0.03622 = 0.03321 0.00922 0.01038 0.00492 AFIX 43 H13 2 1.009461 1.042506 0.031049 11.00000 -1.20000 AFIX 0 C1 1 0.443998 0.669639 0.538500 11.00000 0.05404 0.06066 = 0.03005 -0.00095 -0.00128 -0.01058 AFIX 137 H1A 2 0.526385 0.724353 0.558988 11.00000 -1.50000 H1B 2 0.460872 0.593826 0.559703 11.00000 -1.50000 H1C 2 0.324761 0.695857 0.547213 11.00000 -1.50000 AFIX 0 HKLF 4 REM sjg-rp-03-191-p_mo_a.res in P2(1)2(1)2(1) REM wR2 = 0.1412, GooF = S = 1.210, Restrained GooF = 1.210 for all data REM R1 = 0.0438 for 2709 Fo > 4sig(Fo) and 0.0540 for all 2964 data REM 210 parameters refined using 0 restraints END WGHT 0.0802 0.0000 REM Highest difference peak 0.399, deepest hole -0.735, 1-sigma level 0.181 Q1 1 0.2328 0.8742 0.3733 11.00000 0.05 0.40 Q2 1 0.2961 0.9109 0.3746 11.00000 0.05 0.40 Q3 1 0.2901 0.9153 0.4260 11.00000 0.05 0.38 Q4 1 0.5529 0.6203 0.5611 11.00000 0.05 0.37 Q5 1 0.4090 0.8712 0.3825 11.00000 0.05 0.35 Q6 1 1.0848 0.9170 0.3635 11.00000 0.05 0.35 Q7 1 0.5364 0.5629 0.6041 11.00000 0.05 0.34 Q8 1 0.4146 0.9584 0.4012 11.00000 0.05 0.34 Q9 1 0.9548 1.0173 -0.0991 11.00000 0.05 0.34 Q10 1 0.9924 1.0367 -0.0585 11.00000 0.05 0.33 Q11 1 0.2948 0.8661 0.3267 11.00000 0.05 0.33 Q12 1 0.4705 0.9040 0.3923 11.00000 0.05 0.33 Q13 1 0.9937 0.9638 -0.0627 11.00000 0.05 0.32 Q14 1 0.3888 0.9531 0.4337 11.00000 0.05 0.32 Q15 1 1.0578 1.0031 -0.0011 11.00000 0.05 0.31 Q16 1 0.5826 0.4775 0.2004 11.00000 0.05 0.31 Q17 1 0.9118 0.9307 0.0118 11.00000 0.05 0.31 Q18 1 0.5737 0.8924 0.4121 11.00000 0.05 0.30 Q19 1 0.3951 0.9167 0.3391 11.00000 0.05 0.30 Q20 1 0.8146 0.9561 -0.0545 11.00000 0.05 0.30 ; _shelx_res_checksum 96505 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.212 _oxdiff_exptl_absorpt_empirical_full_min 0.859 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' 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 S1 S 0.54527(11) 0.63587(8) 0.22563(6) 0.0265(3) Uani 1 1 d . O1 O 0.5688(4) 0.5170(2) 0.20903(17) 0.0398(8) Uani 1 1 d . O2 O 0.4046(4) 0.6981(3) 0.19482(16) 0.0361(8) Uani 1 1 d . N1 N 0.7229(4) 0.7017(3) 0.20442(17) 0.0215(8) Uani 1 1 d . C18 C 0.8921(4) 0.6440(3) 0.2189(2) 0.0209(9) Uani 1 1 d . H18 H 0.865620 0.564965 0.236432 0.025 Uiso 1 1 calc R C10 C 0.7140(6) 0.7982(4) 0.0654(2) 0.0359(11) Uani 1 1 d . H10 H 0.637346 0.735585 0.073528 0.043 Uiso 1 1 calc R C5 C 0.5199(4) 0.6449(3) 0.3167(2) 0.0243(9) Uani 1 1 d . C17 C 0.9913(5) 0.7065(3) 0.2762(2) 0.0234(9) Uani 1 1 d . H17A H 1.109795 0.673591 0.279789 0.028 Uiso 1 1 calc R H17B H 0.931725 0.693533 0.321316 0.028 Uiso 1 1 calc R C7 C 0.4227(5) 0.7507(4) 0.4167(2) 0.0330(10) Uani 1 1 d . H7 H 0.371344 0.817805 0.435969 0.040 Uiso 1 1 calc R C4 C 0.5763(5) 0.5568(3) 0.3604(2) 0.0309(10) Uani 1 1 d . H4 H 0.631210 0.490823 0.341242 0.037 Uiso 1 1 calc R C15 C 0.8239(5) 0.8854(3) 0.2544(2) 0.0238(9) Uani 1 1 d . H15A H 0.833675 0.968739 0.244650 0.029 Uiso 1 1 calc R H15B H 0.758983 0.876252 0.298659 0.029 Uiso 1 1 calc R C19 C 0.9956(5) 0.6310(4) 0.1517(2) 0.0269(9) Uani 1 1 d . H19A H 0.924673 0.590729 0.116873 0.040 Uiso 1 1 calc GR H19B H 1.101556 0.586657 0.160885 0.040 Uiso 1 1 calc GR H19C H 1.027102 0.707138 0.133885 0.040 Uiso 1 1 calc GR C9 C 0.7789(5) 0.8601(3) 0.1218(2) 0.0260(9) Uani 1 1 d . C8 C 0.7214(5) 0.8284(3) 0.1956(2) 0.0227(9) Uani 1 1 d . H8 H 0.597719 0.853854 0.200518 0.027 Uiso 1 1 calc R C6 C 0.4443(5) 0.7430(3) 0.3456(2) 0.0269(9) Uani 1 1 d . H6 H 0.407960 0.804250 0.316224 0.032 Uiso 1 1 calc R C2 C 0.4746(5) 0.6618(4) 0.4612(2) 0.0342(10) Uani 1 1 d . C11 C 0.7594(7) 0.8265(5) -0.0021(3) 0.0503(14) Uani 1 1 d . H11 H 0.714072 0.782822 -0.039829 0.060 Uiso 1 1 calc R C16 C 1.0055(5) 0.8354(3) 0.2631(2) 0.0252(9) Uani 1 1 d . H16A H 1.064867 0.872802 0.302938 0.030 Uiso 1 1 calc R H16B H 1.074939 0.849662 0.220508 0.030 Uiso 1 1 calc R C14 C 0.8894(6) 0.9515(4) 0.1072(2) 0.0344(11) Uani 1 1 d . H14 H 0.935428 0.995707 0.144590 0.041 Uiso 1 1 calc R C3 C 0.5523(5) 0.5656(4) 0.4315(3) 0.0350(11) Uani 1 1 d . H3 H 0.589637 0.504535 0.460806 0.042 Uiso 1 1 calc R C12 C 0.8696(8) 0.9173(5) -0.0157(3) 0.0523(15) Uani 1 1 d . H12 H 0.900611 0.936431 -0.062238 0.063 Uiso 1 1 calc R C13 C 0.9337(8) 0.9795(4) 0.0395(3) 0.0443(12) Uani 1 1 d . H13 H 1.009461 1.042506 0.031049 0.053 Uiso 1 1 calc R C1 C 0.4440(7) 0.6696(5) 0.5385(3) 0.0482(13) Uani 1 1 d . H1A H 0.526385 0.724353 0.558988 0.072 Uiso 1 1 calc GR H1B H 0.460872 0.593826 0.559703 0.072 Uiso 1 1 calc GR H1C H 0.324761 0.695857 0.547213 0.072 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 0.0194(4) 0.0298(5) 0.0303(6) -0.0069(5) 0.0015(4) -0.0081(4) O1 0.0403(16) 0.0289(15) 0.050(2) -0.0170(14) 0.0112(16) -0.0164(14) O2 0.0184(13) 0.056(2) 0.034(2) -0.0034(16) -0.0042(13) -0.0044(13) N1 0.0171(14) 0.0189(16) 0.029(2) -0.0007(14) 0.0013(14) 0.0001(13) C18 0.0190(16) 0.0182(18) 0.025(2) -0.0007(18) 0.0003(16) 0.0012(14) C10 0.043(2) 0.035(2) 0.030(3) -0.002(2) -0.015(2) 0.007(2) C5 0.0182(17) 0.026(2) 0.029(2) -0.0018(17) 0.0018(16) -0.0083(17) C17 0.0221(16) 0.0227(19) 0.025(2) 0.0002(17) -0.0002(17) 0.0004(14) C7 0.0294(19) 0.035(2) 0.034(3) -0.007(2) 0.002(2) -0.0038(19) C4 0.0272(19) 0.023(2) 0.043(3) 0.0003(19) 0.001(2) -0.0043(17) C15 0.0301(18) 0.0181(17) 0.023(2) 0.0003(16) 0.0023(17) -0.0020(16) C19 0.0262(18) 0.0265(19) 0.028(2) -0.0010(18) 0.0032(17) 0.0075(17) C9 0.0299(18) 0.0210(18) 0.027(2) 0.0020(17) -0.0037(18) 0.0087(17) C8 0.0205(17) 0.0195(18) 0.028(2) -0.0033(16) -0.0023(17) 0.0012(15) C6 0.0263(19) 0.028(2) 0.026(2) -0.0011(18) 0.0003(19) -0.0026(18) C2 0.030(2) 0.041(3) 0.031(3) 0.000(2) -0.0026(19) -0.0085(19) C11 0.068(3) 0.052(3) 0.031(3) -0.007(2) -0.022(3) 0.020(3) C16 0.0240(16) 0.023(2) 0.028(3) -0.0017(17) -0.0046(17) -0.0056(15) C14 0.044(2) 0.029(2) 0.031(3) 0.001(2) 0.001(2) 0.0007(19) C3 0.034(2) 0.029(2) 0.042(3) 0.012(2) -0.003(2) -0.007(2) C12 0.074(4) 0.053(3) 0.030(3) 0.015(3) 0.006(3) 0.029(3) C13 0.063(3) 0.036(2) 0.033(3) 0.009(2) 0.010(3) 0.005(2) C1 0.054(3) 0.061(3) 0.030(3) -0.001(2) -0.001(2) -0.011(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 O1 S1 N1 107.18(17) O1 S1 C5 107.0(2) O2 S1 O1 119.58(19) O2 S1 N1 107.14(17) O2 S1 C5 107.23(18) N1 S1 C5 108.34(17) C18 N1 S1 118.5(2) C8 N1 S1 119.5(2) C8 N1 C18 118.4(3) N1 C18 H18 107.4 N1 C18 C17 110.9(3) N1 C18 C19 110.1(3) C17 C18 H18 107.4 C17 C18 C19 113.4(3) C19 C18 H18 107.4 C9 C10 H10 119.5 C11 C10 H10 119.5 C11 C10 C9 121.0(5) C4 C5 S1 121.2(3) C4 C5 C6 119.6(4) C6 C5 S1 119.2(3) C18 C17 H17A 109.0 C18 C17 H17B 109.0 C18 C17 C16 112.8(3) H17A C17 H17B 107.8 C16 C17 H17A 109.0 C16 C17 H17B 109.0 C6 C7 H7 119.3 C6 C7 C2 121.4(4) C2 C7 H7 119.3 C5 C4 H4 120.1 C3 C4 C5 119.9(4) C3 C4 H4 120.1 H15A C15 H15B 107.8 C8 C15 H15A 109.0 C8 C15 H15B 109.0 C16 C15 H15A 109.0 C16 C15 H15B 109.0 C16 C15 C8 112.8(3) C18 C19 H19A 109.5 C18 C19 H19B 109.5 C18 C19 H19C 109.5 H19A C19 H19B 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C10 C9 C8 119.4(4) C14 C9 C10 117.3(4) C14 C9 C8 123.3(4) N1 C8 C15 110.1(3) N1 C8 C9 110.1(3) N1 C8 H8 106.9 C15 C8 H8 106.9 C9 C8 C15 115.4(3) C9 C8 H8 106.9 C5 C6 H6 120.1 C7 C6 C5 119.7(4) C7 C6 H6 120.1 C7 C2 C1 120.8(4) C3 C2 C7 117.9(4) C3 C2 C1 121.3(4) C10 C11 H11 119.5 C12 C11 C10 121.0(5) C12 C11 H11 119.5 C17 C16 H16A 109.8 C17 C16 H16B 109.8 C15 C16 C17 109.2(3) C15 C16 H16A 109.8 C15 C16 H16B 109.8 H16A C16 H16B 108.3 C9 C14 H14 119.3 C13 C14 C9 121.4(5) C13 C14 H14 119.3 C4 C3 C2 121.4(4) C4 C3 H3 119.3 C2 C3 H3 119.3 C11 C12 H12 120.7 C13 C12 C11 118.6(5) C13 C12 H12 120.7 C14 C13 H13 119.6 C12 C13 C14 120.8(5) C12 C13 H13 119.6 C2 C1 H1A 109.5 C2 C1 H1B 109.5 C2 C1 H1C 109.5 H1A C1 H1B 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.431(3) S1 O2 1.428(3) S1 N1 1.617(3) S1 C5 1.760(4) N1 C18 1.490(4) N1 C8 1.484(5) C18 H18 1.0000 C18 C17 1.522(5) C18 C19 1.522(5) C10 H10 0.9500 C10 C9 1.391(6) C10 C11 1.381(7) C5 C4 1.392(6) C5 C6 1.395(5) C17 H17A 0.9900 C17 H17B 0.9900 C17 C16 1.525(5) C7 H7 0.9500 C7 C6 1.376(6) C7 C2 1.399(6) C4 H4 0.9500 C4 C3 1.379(6) C15 H15A 0.9900 C15 H15B 0.9900 C15 C8 1.527(5) C15 C16 1.521(5) C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800 C9 C8 1.526(6) C9 C14 1.390(6) C8 H8 1.0000 C6 H6 0.9500 C2 C3 1.391(6) C2 C1 1.503(6) C11 H11 0.9500 C11 C12 1.378(8) C16 H16A 0.9900 C16 H16B 0.9900 C14 H14 0.9500 C14 C13 1.380(6) C3 H3 0.9500 C12 H12 0.9500 C12 C13 1.374(7) C13 H13 0.9500 C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800