#------------------------------------------------------------------------------ #$Date: 2019-05-18 04:09:11 +0300 (Sat, 18 May 2019) $ #$Revision: 215288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123488.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_7123488 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 'C20 H23 N O3 S' _chemical_formula_sum 'C20 H23 N O3 S' _chemical_formula_weight 357.45 _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 6.4626(3) _cell_length_b 7.6863(3) _cell_length_c 36.6394(17) _cell_measurement_reflns_used 5053 _cell_measurement_temperature 150 _cell_measurement_theta_max 30.2810 _cell_measurement_theta_min 2.8690 _cell_volume 1820.01(14) _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 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 -110.00 8.50 0.50 8.00 -- -20.00 -72.00 -36.00 237 2 \w -33.50 15.00 0.50 8.00 -- -20.00 -72.00 108.00 97 3 \w -63.00 -33.50 0.50 8.00 -- -20.00 0.00-108.00 59 ; _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 0.1015922000 _diffrn_orient_matrix_UB_12 -0.0338065000 _diffrn_orient_matrix_UB_13 -0.0018249000 _diffrn_orient_matrix_UB_21 0.0085811000 _diffrn_orient_matrix_UB_22 -0.0057197000 _diffrn_orient_matrix_UB_23 0.0192736000 _diffrn_orient_matrix_UB_31 -0.0406377000 _diffrn_orient_matrix_UB_32 -0.0856466000 _diffrn_orient_matrix_UB_33 -0.0005228000 _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 0.0423 _diffrn_reflns_av_unetI/netI 0.0579 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 6721 _diffrn_reflns_point_group_measured_fraction_full 0.980 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 24.993 _diffrn_reflns_theta_max 24.993 _diffrn_reflns_theta_min 2.223 _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 0.196 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89066 _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 1.305 _exptl_crystal_description block _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.215 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.225 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.062 _refine_ls_abs_structure_details ; Flack x determined using 993 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.01(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3129 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0398 _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^)+(0.0377P)^2^+0.2993P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0852 _refine_ls_wR_factor_ref 0.0921 _reflns_Friedel_coverage 0.655 _reflns_Friedel_fraction_full 0.955 _reflns_Friedel_fraction_max 0.955 _reflns_number_gt 2815 _reflns_number_total 3129 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc03127h2.cif _cod_data_source_block sjg-rp-03-207_mo _cod_database_code 7123488 _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 0.971 _shelx_estimated_absorpt_t_min 0.959 _reflns_odcompleteness_completeness 91.74 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.03 _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: C8(H8) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C10(H10A,H10B) 2.c Aromatic/amide H refined with riding coordinates: C19(H19), C15(H15), C6(H6), C7(H7), C12(H12), C18(H18), C3(H3), C16(H16), C4(H4) 2.d Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL sjg-rp-03-207_mo_a.res in P2(1)2(1)2(1) sjg-rp-03-207_mo.res created by SHELXL-2018/3 at 16:10:19 on 18-Oct-2018 REM Old TITL SJG-RP-03-207_Mo in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.192, Rweak 0.049, Alpha 0.002, Orientation as input REM Flack x = 0.142 ( 0.052 ) from Parsons' quotients REM Formula found by SHELXT: C20 N O3 Cl CELL 0.71073 6.462601 7.686325 36.639395 90 90 90 ZERR 4 0.000264 0.000324 0.001664 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 80 92 4 12 4 L.S. 100 PLAN 20 SIZE 0.15 0.19 0.215 TEMP -123.15 list 4 fmap 2 acta OMIT -3 50 OMIT 2 0 0 OMIT 0 1 4 OMIT 0 1 1 OMIT 0 1 5 OMIT 0 1 2 OMIT 0 1 6 REM REM REM WGHT 0.037700 0.299300 FVAR 3.58562 S1 5 0.384175 0.598296 0.650675 11.00000 0.02481 0.02630 = 0.02525 -0.00427 0.00029 0.00360 O3 4 0.758320 1.050997 0.505712 11.00000 0.04009 0.03032 = 0.03301 0.00679 0.00165 -0.00428 O2 4 0.418046 0.768102 0.635713 11.00000 0.04920 0.02184 = 0.03336 -0.00047 -0.00047 0.01021 O1 4 0.177550 0.544087 0.659245 11.00000 0.02218 0.04736 = 0.03633 -0.01108 0.00158 0.00033 N1 3 0.475127 0.454616 0.620991 11.00000 0.02319 0.02223 = 0.02221 -0.00141 0.00103 -0.00225 C19 1 0.532440 0.693941 0.556363 11.00000 0.02456 0.02399 = 0.02662 -0.00431 -0.00039 -0.00206 AFIX 43 H19 2 0.403369 0.634919 0.557186 11.00000 -1.20000 AFIX 0 C13 1 0.673129 0.488491 0.603992 11.00000 0.02329 0.02417 = 0.02144 -0.00509 -0.00099 0.00019 C14 1 0.692086 0.642947 0.579833 11.00000 0.02451 0.02450 = 0.01894 -0.00280 0.00062 0.00244 C15 1 0.877723 0.734415 0.578395 11.00000 0.02529 0.03370 = 0.02299 -0.00169 -0.00151 0.00133 AFIX 43 H15 2 0.987266 0.702326 0.594321 11.00000 -1.20000 AFIX 0 C6 1 0.733720 0.646572 0.691439 11.00000 0.02892 0.02994 = 0.02341 -0.00416 0.00394 -0.00102 AFIX 43 H6 2 0.792414 0.696762 0.670126 11.00000 -1.20000 AFIX 0 C2 1 0.765696 0.565313 0.755006 11.00000 0.04114 0.03162 = 0.02421 -0.00827 -0.00593 0.01096 C7 1 0.847794 0.635410 0.723357 11.00000 0.02460 0.03877 = 0.03294 -0.01107 -0.00090 0.00048 AFIX 43 H7 2 0.986213 0.677011 0.723535 11.00000 -1.20000 AFIX 0 C11 1 0.814931 0.204607 0.627330 11.00000 0.03304 0.03009 = 0.03401 -0.00053 -0.00753 0.00633 AFIX 23 H11A 2 0.936733 0.197538 0.643649 11.00000 -1.20000 H11B 2 0.822230 0.105762 0.610054 11.00000 -1.20000 AFIX 0 C10 1 0.618992 0.188360 0.650060 11.00000 0.04653 0.02124 = 0.02386 0.00015 -0.00438 -0.00027 AFIX 23 H10A 2 0.638172 0.249129 0.673642 11.00000 -1.20000 H10B 2 0.591211 0.064115 0.655228 11.00000 -1.20000 AFIX 0 C9 1 0.384060 0.171132 0.594709 11.00000 0.03457 0.02556 = 0.03761 -0.00550 -0.00716 0.00156 AFIX 137 H9A 2 0.262936 0.224549 0.583159 11.00000 -1.50000 H9B 2 0.354050 0.049022 0.600293 11.00000 -1.50000 H9C 2 0.502452 0.177629 0.578051 11.00000 -1.50000 AFIX 0 C12 1 0.823857 0.370400 0.606451 11.00000 0.02593 0.03094 = 0.02655 -0.00263 -0.00135 0.00186 AFIX 43 H12 2 0.948516 0.394474 0.593672 11.00000 -1.20000 AFIX 0 C18 1 0.560189 0.828509 0.532116 11.00000 0.02861 0.02458 = 0.02361 -0.00038 -0.00372 0.00282 AFIX 43 H18 2 0.450626 0.860763 0.516209 11.00000 -1.20000 AFIX 0 C8 1 0.434740 0.267404 0.629727 11.00000 0.02949 0.02126 = 0.02526 0.00025 0.00292 -0.00064 AFIX 13 H8 2 0.311073 0.261401 0.646083 11.00000 -1.20000 AFIX 0 C5 1 0.531200 0.583039 0.691005 11.00000 0.02444 0.02169 = 0.02395 -0.00739 0.00066 -0.00006 C3 1 0.564244 0.499521 0.753793 11.00000 0.04416 0.02918 = 0.02268 0.00016 0.00577 0.00051 AFIX 43 H3 2 0.506160 0.448468 0.775068 11.00000 -1.20000 AFIX 0 C17 1 0.747447 0.917944 0.530666 11.00000 0.03467 0.02424 = 0.02131 -0.00169 0.00235 0.00114 C16 1 0.906731 0.871722 0.554195 11.00000 0.02612 0.03129 = 0.02884 -0.00472 0.00378 -0.00553 AFIX 43 H16 2 1.034197 0.933252 0.553767 11.00000 -1.20000 AFIX 0 C4 1 0.447334 0.507514 0.721969 11.00000 0.03237 0.02444 = 0.03139 -0.00233 0.00505 -0.00360 AFIX 43 H4 2 0.310932 0.461497 0.721475 11.00000 -1.20000 AFIX 0 C20 1 0.940160 1.155388 0.505579 11.00000 0.04992 0.03958 = 0.03766 0.00432 0.00203 -0.01435 AFIX 137 H20A 2 0.924933 1.248989 0.487617 11.00000 -1.50000 H20B 2 1.059789 1.083259 0.499158 11.00000 -1.50000 H20C 2 0.960992 1.205808 0.529869 11.00000 -1.50000 AFIX 0 C1 1 0.889827 0.563510 0.789861 11.00000 0.05173 0.05290 = 0.03205 -0.00715 -0.01096 0.01379 AFIX 137 H1A 2 1.029083 0.519027 0.784860 11.00000 -1.50000 H1B 2 0.821507 0.488324 0.807789 11.00000 -1.50000 H1C 2 0.899551 0.682008 0.799583 11.00000 -1.50000 AFIX 0 HKLF 4 REM sjg-rp-03-207_mo_a.res in P2(1)2(1)2(1) REM wR2 = 0.0921, GooF = S = 1.042, Restrained GooF = 1.042 for all data REM R1 = 0.0398 for 2815 Fo > 4sig(Fo) and 0.0487 for all 3129 data REM 229 parameters refined using 0 restraints END WGHT 0.0372 0.2976 REM Highest difference peak 0.225, deepest hole -0.315, 1-sigma level 0.062 Q1 1 0.8365 0.5942 0.7717 11.00000 0.05 0.23 Q2 1 1.1657 0.7747 0.7734 11.00000 0.05 0.20 Q3 1 0.1227 0.5194 0.6957 11.00000 0.05 0.19 Q4 1 1.0345 0.6640 0.7694 11.00000 0.05 0.19 Q5 1 1.1955 0.5921 0.7681 11.00000 0.05 0.19 Q6 1 0.7727 1.0906 0.4765 11.00000 0.05 0.19 Q7 1 1.2435 0.6599 0.7597 11.00000 0.05 0.18 Q8 1 0.7909 0.7488 0.7723 11.00000 0.05 0.18 Q9 1 0.7703 0.9982 0.4738 11.00000 0.05 0.18 Q10 1 1.0393 0.8454 0.7724 11.00000 0.05 0.18 Q11 1 1.2308 1.0699 0.4799 11.00000 0.05 0.17 Q12 1 1.1868 1.1596 0.4717 11.00000 0.05 0.17 Q13 1 0.4486 0.6041 0.6786 11.00000 0.05 0.17 Q14 1 1.1941 1.0197 0.4730 11.00000 0.05 0.17 Q15 1 0.5119 0.6788 0.7700 11.00000 0.05 0.17 Q16 1 0.9054 0.8442 0.7919 11.00000 0.05 0.16 Q17 1 0.5068 0.6922 0.7832 11.00000 0.05 0.16 Q18 1 0.9939 1.2761 0.5320 11.00000 0.05 0.16 Q19 1 0.2335 0.6337 0.7002 11.00000 0.05 0.16 Q20 1 1.1160 0.8971 0.5523 11.00000 0.05 0.16 ; _shelx_res_checksum 9623 _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 1.363 _oxdiff_exptl_absorpt_empirical_full_min 0.860 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 0.38417(13) 0.59830(10) 0.65067(2) 0.0255(2) Uani 1 1 d . O3 O 0.7583(4) 1.0510(3) 0.50571(7) 0.0345(6) Uani 1 1 d . O2 O 0.4180(4) 0.7681(3) 0.63571(7) 0.0348(6) Uani 1 1 d . O1 O 0.1776(3) 0.5441(3) 0.65924(7) 0.0353(6) Uani 1 1 d . N1 N 0.4751(4) 0.4546(4) 0.62099(7) 0.0225(6) Uani 1 1 d . C19 C 0.5324(5) 0.6939(4) 0.55636(9) 0.0251(8) Uani 1 1 d . H19 H 0.403369 0.634919 0.557186 0.030 Uiso 1 1 calc R C13 C 0.6731(5) 0.4885(4) 0.60399(9) 0.0230(7) Uani 1 1 d . C14 C 0.6921(5) 0.6429(4) 0.57983(8) 0.0226(8) Uani 1 1 d . C15 C 0.8777(5) 0.7344(4) 0.57840(9) 0.0273(8) Uani 1 1 d . H15 H 0.987266 0.702326 0.594321 0.033 Uiso 1 1 calc R C6 C 0.7337(5) 0.6466(4) 0.69144(9) 0.0274(8) Uani 1 1 d . H6 H 0.792414 0.696762 0.670126 0.033 Uiso 1 1 calc R C2 C 0.7657(5) 0.5653(5) 0.75501(10) 0.0323(9) Uani 1 1 d . C7 C 0.8478(5) 0.6354(5) 0.72336(9) 0.0321(9) Uani 1 1 d . H7 H 0.986213 0.677011 0.723535 0.039 Uiso 1 1 calc R C11 C 0.8149(5) 0.2046(5) 0.62733(11) 0.0324(9) Uani 1 1 d . H11A H 0.936733 0.197538 0.643649 0.039 Uiso 1 1 calc R H11B H 0.822230 0.105762 0.610054 0.039 Uiso 1 1 calc R C10 C 0.6190(5) 0.1884(4) 0.65006(9) 0.0305(8) Uani 1 1 d . H10A H 0.638172 0.249129 0.673642 0.037 Uiso 1 1 calc R H10B H 0.591211 0.064115 0.655228 0.037 Uiso 1 1 calc R C9 C 0.3841(6) 0.1711(4) 0.59471(10) 0.0326(8) Uani 1 1 d . H9A H 0.262936 0.224549 0.583159 0.049 Uiso 1 1 calc GR H9B H 0.354050 0.049022 0.600293 0.049 Uiso 1 1 calc GR H9C H 0.502452 0.177629 0.578051 0.049 Uiso 1 1 calc GR C12 C 0.8239(5) 0.3704(4) 0.60645(9) 0.0278(8) Uani 1 1 d . H12 H 0.948516 0.394474 0.593672 0.033 Uiso 1 1 calc R C18 C 0.5602(5) 0.8285(4) 0.53212(9) 0.0256(8) Uani 1 1 d . H18 H 0.450626 0.860763 0.516209 0.031 Uiso 1 1 calc R C8 C 0.4347(5) 0.2674(4) 0.62973(10) 0.0253(8) Uani 1 1 d . H8 H 0.311073 0.261401 0.646083 0.030 Uiso 1 1 calc R C5 C 0.5312(5) 0.5830(4) 0.69101(9) 0.0234(7) Uani 1 1 d . C3 C 0.5642(5) 0.4995(5) 0.75379(10) 0.0320(9) Uani 1 1 d . H3 H 0.506160 0.448468 0.775068 0.038 Uiso 1 1 calc R C17 C 0.7474(5) 0.9179(4) 0.53067(9) 0.0267(8) Uani 1 1 d . C16 C 0.9067(5) 0.8717(4) 0.55420(9) 0.0288(8) Uani 1 1 d . H16 H 1.034197 0.933252 0.553767 0.035 Uiso 1 1 calc R C4 C 0.4473(5) 0.5075(4) 0.72197(10) 0.0294(8) Uani 1 1 d . H4 H 0.310932 0.461497 0.721475 0.035 Uiso 1 1 calc R C20 C 0.9402(6) 1.1554(5) 0.50558(11) 0.0424(10) Uani 1 1 d . H20A H 0.924933 1.248989 0.487617 0.064 Uiso 1 1 calc GR H20B H 1.059789 1.083259 0.499158 0.064 Uiso 1 1 calc GR H20C H 0.960992 1.205808 0.529869 0.064 Uiso 1 1 calc GR C1 C 0.8898(7) 0.5635(6) 0.78986(10) 0.0456(10) Uani 1 1 d . H1A H 1.029083 0.519027 0.784860 0.068 Uiso 1 1 calc GR H1B H 0.821507 0.488324 0.807789 0.068 Uiso 1 1 calc GR H1C H 0.899551 0.682008 0.799583 0.068 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 0.0248(4) 0.0263(4) 0.0252(5) -0.0043(4) 0.0003(4) 0.0036(4) O3 0.0401(14) 0.0303(13) 0.0330(15) 0.0068(12) 0.0017(11) -0.0043(11) O2 0.0492(16) 0.0218(12) 0.0334(15) -0.0005(11) -0.0005(12) 0.0102(12) O1 0.0222(12) 0.0474(15) 0.0363(16) -0.0111(13) 0.0016(10) 0.0003(11) N1 0.0232(14) 0.0222(14) 0.0222(16) -0.0014(13) 0.0010(11) -0.0023(11) C19 0.0246(16) 0.0240(17) 0.0266(19) -0.0043(16) -0.0004(14) -0.0021(15) C13 0.0233(17) 0.0242(17) 0.0214(18) -0.0051(15) -0.0010(13) 0.0002(14) C14 0.0245(17) 0.0245(17) 0.0189(18) -0.0028(15) 0.0006(13) 0.0024(15) C15 0.0253(17) 0.0337(19) 0.0230(18) -0.0017(16) -0.0015(15) 0.0013(17) C6 0.0289(18) 0.0299(19) 0.0234(19) -0.0042(16) 0.0039(15) -0.0010(15) C2 0.041(2) 0.032(2) 0.024(2) -0.0083(17) -0.0059(16) 0.0110(18) C7 0.0246(18) 0.039(2) 0.033(2) -0.0111(18) -0.0009(15) 0.0005(16) C11 0.033(2) 0.0301(19) 0.034(2) -0.0005(17) -0.0075(16) 0.0063(16) C10 0.047(2) 0.0212(16) 0.0239(18) 0.0001(16) -0.0044(18) -0.0003(17) C9 0.0346(19) 0.0256(17) 0.038(2) -0.0055(17) -0.0072(18) 0.0016(17) C12 0.0259(18) 0.0309(18) 0.0266(19) -0.0026(17) -0.0014(14) 0.0019(15) C18 0.0286(18) 0.0246(17) 0.0236(19) -0.0004(16) -0.0037(14) 0.0028(15) C8 0.0295(19) 0.0213(17) 0.0253(19) 0.0003(15) 0.0029(15) -0.0006(14) C5 0.0244(16) 0.0217(17) 0.0240(18) -0.0074(15) 0.0007(13) -0.0001(15) C3 0.044(2) 0.0292(19) 0.0227(19) 0.0002(16) 0.0058(16) 0.0005(18) C17 0.0347(19) 0.0242(18) 0.0213(18) -0.0017(16) 0.0024(15) 0.0011(16) C16 0.0261(17) 0.0313(18) 0.029(2) -0.0047(17) 0.0038(15) -0.0055(16) C4 0.0324(18) 0.0244(18) 0.031(2) -0.0023(17) 0.0051(15) -0.0036(16) C20 0.050(2) 0.040(2) 0.038(2) 0.004(2) 0.0020(19) -0.0143(19) C1 0.052(2) 0.053(2) 0.032(2) -0.007(2) -0.0110(19) 0.014(2) 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 O2 S1 O1 119.40(15) O2 S1 N1 107.56(15) O2 S1 C5 107.42(15) O1 S1 N1 106.28(14) O1 S1 C5 107.43(15) N1 S1 C5 108.35(14) C17 O3 C20 117.7(3) C13 N1 S1 118.4(2) C13 N1 C8 114.8(3) C8 N1 S1 116.0(2) C18 C19 C14 120.8(3) N1 C13 C14 118.2(3) C12 C13 N1 119.6(3) C12 C13 C14 121.6(3) C19 C14 C13 121.9(3) C15 C14 C19 118.1(3) C15 C14 C13 119.8(3) C16 C15 C14 121.6(3) C7 C6 C5 119.1(3) C7 C2 C3 118.1(3) C7 C2 C1 120.6(3) C3 C2 C1 121.3(3) C2 C7 C6 121.8(3) C12 C11 C10 112.6(3) C11 C10 C8 110.4(3) C13 C12 C11 126.1(3) C19 C18 C17 120.6(3) N1 C8 C10 110.5(3) N1 C8 C9 109.0(3) C9 C8 C10 112.7(3) C6 C5 S1 119.5(3) C4 C5 S1 120.3(2) C4 C5 C6 120.3(3) C4 C3 C2 121.1(3) O3 C17 C18 115.9(3) O3 C17 C16 124.4(3) C16 C17 C18 119.6(3) C17 C16 C15 119.3(3) C5 C4 C3 119.5(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O2 1.432(2) S1 O1 1.434(2) S1 N1 1.658(3) S1 C5 1.761(3) O3 C17 1.374(4) O3 C20 1.423(4) N1 C13 1.447(4) N1 C8 1.497(4) C19 C14 1.399(4) C19 C18 1.375(5) C13 C14 1.486(4) C13 C12 1.334(4) C14 C15 1.392(5) C15 C16 1.391(5) C6 C7 1.385(5) C6 C5 1.397(4) C2 C7 1.384(5) C2 C3 1.397(5) C2 C1 1.508(5) C11 C10 1.521(5) C11 C12 1.487(5) C10 C8 1.530(5) C9 C8 1.517(5) C18 C17 1.393(4) C5 C4 1.385(5) C3 C4 1.391(5) C17 C16 1.389(5)