#------------------------------------------------------------------------------ #$Date: 2019-05-18 04:09:11 +0300 (Sat, 18 May 2019) $ #$Revision: 215288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123487.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_7123487 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 'C21 H27 N O2 S' _chemical_formula_sum 'C21 H27 N O2 S' _chemical_formula_weight 357.49 _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 8.0063(3) _cell_length_b 12.0533(8) _cell_length_c 19.6151(7) _cell_measurement_reflns_used 4333 _cell_measurement_temperature 150 _cell_measurement_theta_max 30.7980 _cell_measurement_theta_min 2.6700 _cell_volume 1892.90(16) _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 0.993 _diffrn_measured_fraction_theta_max 0.993 _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 -59.00 70.00 0.50 8.00 -- -20.00 72.00 36.00 258 2 \w -102.00 -73.50 0.50 8.00 -- -20.00 -72.00 36.00 57 ; _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 0.0077519000 _diffrn_orient_matrix_UB_12 -0.0021322000 _diffrn_orient_matrix_UB_13 0.0359793000 _diffrn_orient_matrix_UB_21 0.0867668000 _diffrn_orient_matrix_UB_22 0.0109232000 _diffrn_orient_matrix_UB_23 -0.0029169000 _diffrn_orient_matrix_UB_31 -0.0163108000 _diffrn_orient_matrix_UB_32 0.0577897000 _diffrn_orient_matrix_UB_33 0.0018520000 _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 0.0417 _diffrn_reflns_av_unetI/netI 0.0588 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 5668 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 24.998 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.677 _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 0.185 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.67190 _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 1.254 _exptl_crystal_description block _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.102 _refine_diff_density_max 0.289 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.103 _refine_ls_abs_structure_details ; Flack x determined using 1012 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.11(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 3261 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0487 _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^)+(0.0534P)^2^+0.6757P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1113 _refine_ls_wR_factor_ref 0.1204 _reflns_Friedel_coverage 0.705 _reflns_Friedel_fraction_full 0.960 _reflns_Friedel_fraction_max 0.960 _reflns_number_gt 2885 _reflns_number_total 3261 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc03127h2.cif _cod_data_source_block sjg-rp-03-217-p_mo _cod_database_code 7123487 _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 0.981 _shelx_estimated_absorpt_t_min 0.962 _reflns_odcompleteness_completeness 89.38 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.15 _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), C12(H12) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B) 2.c Aromatic/amide H refined with riding coordinates: C19(H19), C6(H6), C17(H17), C7(H7), C15(H15), C4(H4), C3(H3) 2.d Idealised Me refined as rotating group: C21(H21A,H21B,H21C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL sjg-rp-03-217-p_mo_a.res in P2(1)2(1)2(1) sjg-rp-03-217-p_mo.res created by SHELXL-2018/3 at 16:42:47 on 18-Oct-2018 REM Old TITL SJG-RP-03-217-P_Mo in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.191, Rweak 0.027, Alpha 0.002, Orientation as input REM Flack x = 0.202 ( 0.153 ) from Parsons' quotients REM Formula found by SHELXT: C21 N3 Cl CELL 0.71073 8.0063 12.0533 19.6151 90 90 90 ZERR 4 0.0003 0.0008 0.0007 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 84 108 4 8 4 L.S. 100 PLAN 20 SIZE 0.102 0.15 0.21 TEMP -123.15 BOND $H list 4 fmap 2 acta OMIT -3 50 OMIT 0 1 1 OMIT 1 0 2 OMIT 0 0 2 REM REM REM WGHT 0.053400 0.675700 FVAR 0.65982 S1 5 0.060658 -0.751237 -0.732926 11.00000 0.01898 0.06427 = 0.02147 -0.00553 -0.00092 -0.00045 O1 4 0.119053 -0.644330 -0.711484 11.00000 0.03329 0.08783 = 0.03671 -0.02518 0.00448 -0.02909 O2 4 0.141264 -0.848565 -0.708380 11.00000 0.03083 0.10020 = 0.03014 0.01659 0.00052 0.02486 N1 3 -0.135358 -0.759421 -0.712255 11.00000 0.01836 0.03336 = 0.02245 -0.00520 0.00220 0.00096 C19 1 -0.477262 -0.613097 -0.626632 11.00000 0.03004 0.02472 = 0.02255 0.00170 -0.00011 0.00027 AFIX 43 H19 2 -0.550421 -0.606752 -0.664563 11.00000 -1.20000 AFIX 0 C16 1 -0.261990 -0.628513 -0.515791 11.00000 0.03046 0.02419 = 0.02114 -0.00001 0.00134 -0.00234 C6 1 0.031554 -0.662053 -0.860045 11.00000 0.04410 0.02360 = 0.03347 -0.00539 0.01245 -0.00624 AFIX 43 H6 2 0.009911 -0.593791 -0.837503 11.00000 -1.20000 AFIX 0 C18 1 -0.538823 -0.593625 -0.560893 11.00000 0.02841 0.02419 = 0.02712 -0.00247 0.00155 0.00127 C17 1 -0.430672 -0.602457 -0.506368 11.00000 0.03589 0.02624 = 0.02053 -0.00251 0.00434 0.00313 AFIX 43 H17 2 -0.471644 -0.590592 -0.461503 11.00000 -1.20000 AFIX 0 C14 1 -0.311206 -0.641521 -0.637414 11.00000 0.02976 0.01797 = 0.02210 -0.00094 0.00331 -0.00227 C7 1 0.024624 -0.668247 -0.930793 11.00000 0.06294 0.03380 = 0.03649 0.01014 0.01788 0.00672 AFIX 43 H7 2 -0.001728 -0.603737 -0.956455 11.00000 -1.20000 AFIX 0 C15 1 -0.205425 -0.648234 -0.581395 11.00000 0.02147 0.02486 = 0.02550 -0.00246 0.00267 0.00021 AFIX 43 H15 2 -0.091362 -0.666834 -0.588284 11.00000 -1.20000 AFIX 0 C5 1 0.069944 -0.755410 -0.822977 11.00000 0.01892 0.03831 = 0.02095 -0.00450 0.00292 0.00001 C2 1 0.055356 -0.766325 -0.963994 11.00000 0.03685 0.04511 = 0.02686 -0.00148 0.00792 0.00024 C4 1 0.104045 -0.854200 -0.855663 11.00000 0.04886 0.04129 = 0.03119 0.00679 0.01038 0.01923 AFIX 43 H4 2 0.132624 -0.918478 -0.830178 11.00000 -1.20000 AFIX 0 C8 1 -0.220935 -0.867166 -0.724687 11.00000 0.03263 0.02833 = 0.02605 -0.00376 0.00491 0.00007 AFIX 13 H8 2 -0.133564 -0.921760 -0.738894 11.00000 -1.20000 AFIX 0 C11 1 -0.363990 -0.654312 -0.767732 11.00000 0.03482 0.03840 = 0.01938 0.00305 0.00362 0.00879 AFIX 23 H11A 2 -0.441696 -0.591437 -0.760762 11.00000 -1.20000 H11B 2 -0.303364 -0.641332 -0.810991 11.00000 -1.20000 AFIX 0 C21 1 -0.145286 -0.629288 -0.455233 11.00000 0.03459 0.03650 = 0.02373 -0.00121 -0.00348 0.00203 AFIX 137 H21A 2 -0.110543 -0.553187 -0.444831 11.00000 -1.50000 H21B 2 -0.046700 -0.674235 -0.465914 11.00000 -1.50000 H21C 2 -0.202939 -0.660946 -0.415686 11.00000 -1.50000 AFIX 0 C9 1 -0.344719 -0.857114 -0.783212 11.00000 0.03353 0.03854 = 0.02640 -0.00974 0.00180 -0.00802 AFIX 23 H9A 2 -0.282552 -0.847149 -0.826408 11.00000 -1.20000 H9B 2 -0.409703 -0.926752 -0.786766 11.00000 -1.20000 AFIX 0 C13 1 -0.299686 -0.910686 -0.659209 11.00000 0.04747 0.03340 = 0.03140 -0.00096 0.00365 -0.00517 AFIX 137 H13A 2 -0.215203 -0.912924 -0.623082 11.00000 -1.50000 H13B 2 -0.343326 -0.985585 -0.666991 11.00000 -1.50000 H13C 2 -0.391175 -0.861534 -0.645446 11.00000 -1.50000 AFIX 0 C20 1 -0.721167 -0.565708 -0.550543 11.00000 0.03021 0.05252 = 0.03318 -0.00829 0.00239 0.00853 AFIX 137 H20A 2 -0.731397 -0.488804 -0.534874 11.00000 -1.50000 H20B 2 -0.769085 -0.615645 -0.516308 11.00000 -1.50000 H20C 2 -0.781215 -0.574580 -0.593736 11.00000 -1.50000 AFIX 0 C12 1 -0.238850 -0.656945 -0.709328 11.00000 0.03079 0.02659 = 0.02309 -0.00171 0.00189 -0.00050 AFIX 13 H12 2 -0.160780 -0.593408 -0.717029 11.00000 -1.20000 AFIX 0 C3 1 0.095982 -0.858374 -0.926571 11.00000 0.06516 0.03335 = 0.03098 -0.00215 0.01480 0.00660 AFIX 43 H3 2 0.119055 -0.926223 -0.949346 11.00000 -1.20000 AFIX 0 C10 1 -0.464050 -0.760579 -0.773783 11.00000 0.02358 0.06076 = 0.02264 -0.00536 -0.00152 0.00006 AFIX 23 H10A 2 -0.540807 -0.755804 -0.813244 11.00000 -1.20000 H10B 2 -0.531697 -0.771824 -0.732103 11.00000 -1.20000 AFIX 0 C1 1 0.043801 -0.772164 -1.041483 11.00000 0.07199 0.07663 = 0.02485 0.00538 0.00877 0.00768 AFIX 137 H1A 2 -0.038901 -0.828215 -1.054535 11.00000 -1.50000 H1B 2 0.153023 -0.792335 -1.060325 11.00000 -1.50000 H1C 2 0.009851 -0.699697 -1.059404 11.00000 -1.50000 AFIX 0 HKLF 4 REM sjg-rp-03-217-p_mo_a.res in P2(1)2(1)2(1) REM wR2 = 0.1204, GooF = S = 1.036, Restrained GooF = 1.036 for all data REM R1 = 0.0487 for 2885 Fo > 4sig(Fo) and 0.0596 for all 3261 data REM 230 parameters refined using 0 restraints END WGHT 0.0534 0.6757 REM Highest difference peak 0.289, deepest hole -0.505, 1-sigma level 0.103 Q1 1 0.0945 -0.6646 -0.8894 11.00000 0.05 0.29 Q2 1 -0.0943 -0.9058 -0.6067 11.00000 0.05 0.25 Q3 1 -0.0409 -0.6788 -0.8884 11.00000 0.05 0.25 Q4 1 -0.5201 -0.8887 -0.6464 11.00000 0.05 0.25 Q5 1 0.2488 -0.6296 -0.8921 11.00000 0.05 0.24 Q6 1 -0.0540 -0.8231 -0.6413 11.00000 0.05 0.24 Q7 1 -0.0606 -0.9728 -0.6396 11.00000 0.05 0.24 Q8 1 -0.2410 -0.9766 -0.6167 11.00000 0.05 0.24 Q9 1 0.1423 -0.8378 -0.8833 11.00000 0.05 0.24 Q10 1 -0.0966 -0.8605 -0.5931 11.00000 0.05 0.23 Q11 1 -0.2147 -1.0260 -0.6499 11.00000 0.05 0.23 Q12 1 -0.0396 -0.6850 -0.6405 11.00000 0.05 0.23 Q13 1 0.2762 -0.8030 -1.1033 11.00000 0.05 0.23 Q14 1 -0.0501 -0.6218 -0.6060 11.00000 0.05 0.23 Q15 1 -0.3840 -0.7345 -0.3962 11.00000 0.05 0.22 Q16 1 -0.0227 -0.5730 -0.8931 11.00000 0.05 0.22 Q17 1 0.0795 -0.5580 -0.8447 11.00000 0.05 0.22 Q18 1 -0.5065 -1.0579 -0.6312 11.00000 0.05 0.22 Q19 1 -0.4601 -0.6079 -0.3836 11.00000 0.05 0.22 Q20 1 -0.2513 -0.6779 -0.6098 11.00000 0.05 0.22 ; _shelx_res_checksum 26325 _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 1.398 _oxdiff_exptl_absorpt_empirical_full_min 0.810 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 0.06066(11) -0.75124(10) -0.73293(4) 0.0349(3) Uani 1 1 d . O1 O 0.1191(4) -0.6443(3) -0.71148(14) 0.0526(10) Uani 1 1 d . O2 O 0.1413(4) -0.8486(3) -0.70838(13) 0.0537(10) Uani 1 1 d . N1 N -0.1354(4) -0.7594(3) -0.71225(12) 0.0247(7) Uani 1 1 d . C19 C -0.4773(5) -0.6131(3) -0.62663(17) 0.0258(8) Uani 1 1 d . H19 H -0.550421 -0.606752 -0.664563 0.031 Uiso 1 1 calc R C16 C -0.2620(5) -0.6285(3) -0.51579(17) 0.0253(8) Uani 1 1 d . C6 C 0.0316(6) -0.6621(3) -0.86004(19) 0.0337(10) Uani 1 1 d . H6 H 0.009911 -0.593791 -0.837503 0.040 Uiso 1 1 calc R C18 C -0.5388(5) -0.5936(3) -0.56089(18) 0.0266(8) Uani 1 1 d . C17 C -0.4307(5) -0.6025(3) -0.50637(16) 0.0276(8) Uani 1 1 d . H17 H -0.471644 -0.590592 -0.461503 0.033 Uiso 1 1 calc R C14 C -0.3112(5) -0.6415(3) -0.63741(17) 0.0233(8) Uani 1 1 d . C7 C 0.0246(7) -0.6682(4) -0.9308(2) 0.0444(12) Uani 1 1 d . H7 H -0.001728 -0.603737 -0.956455 0.053 Uiso 1 1 calc R C15 C -0.2054(5) -0.6482(3) -0.58139(16) 0.0239(8) Uani 1 1 d . H15 H -0.091362 -0.666834 -0.588284 0.029 Uiso 1 1 calc R C5 C 0.0699(4) -0.7554(3) -0.82298(16) 0.0261(8) Uani 1 1 d . C2 C 0.0554(5) -0.7663(4) -0.96399(18) 0.0363(9) Uani 1 1 d . C4 C 0.1040(6) -0.8542(4) -0.8557(2) 0.0404(11) Uani 1 1 d . H4 H 0.132624 -0.918478 -0.830178 0.049 Uiso 1 1 calc R C8 C -0.2209(5) -0.8672(3) -0.72469(18) 0.0290(9) Uani 1 1 d . H8 H -0.133564 -0.921760 -0.738894 0.035 Uiso 1 1 calc R C11 C -0.3640(5) -0.6543(3) -0.76773(19) 0.0309(9) Uani 1 1 d . H11A H -0.441696 -0.591437 -0.760762 0.037 Uiso 1 1 calc R H11B H -0.303364 -0.641332 -0.810991 0.037 Uiso 1 1 calc R C21 C -0.1453(5) -0.6293(3) -0.45523(17) 0.0316(9) Uani 1 1 d . H21A H -0.110543 -0.553187 -0.444831 0.047 Uiso 1 1 calc GR H21B H -0.046700 -0.674235 -0.465914 0.047 Uiso 1 1 calc GR H21C H -0.202939 -0.660946 -0.415686 0.047 Uiso 1 1 calc GR C9 C -0.3447(5) -0.8571(3) -0.78321(18) 0.0328(9) Uani 1 1 d . H9A H -0.282552 -0.847149 -0.826408 0.039 Uiso 1 1 calc R H9B H -0.409703 -0.926752 -0.786766 0.039 Uiso 1 1 calc R C13 C -0.2997(6) -0.9107(3) -0.65921(19) 0.0374(10) Uani 1 1 d . H13A H -0.215203 -0.912924 -0.623082 0.056 Uiso 1 1 calc GR H13B H -0.343326 -0.985585 -0.666991 0.056 Uiso 1 1 calc GR H13C H -0.391175 -0.861534 -0.645446 0.056 Uiso 1 1 calc GR C20 C -0.7212(5) -0.5657(4) -0.5505(2) 0.0386(10) Uani 1 1 d . H20A H -0.731397 -0.488804 -0.534874 0.058 Uiso 1 1 calc GR H20B H -0.769085 -0.615645 -0.516308 0.058 Uiso 1 1 calc GR H20C H -0.781215 -0.574580 -0.593736 0.058 Uiso 1 1 calc GR C12 C -0.2388(5) -0.6569(3) -0.70933(17) 0.0268(9) Uani 1 1 d . H12 H -0.160780 -0.593408 -0.717029 0.032 Uiso 1 1 calc R C3 C 0.0960(6) -0.8584(4) -0.9266(2) 0.0432(12) Uani 1 1 d . H3 H 0.119055 -0.926223 -0.949346 0.052 Uiso 1 1 calc R C10 C -0.4641(5) -0.7606(4) -0.77378(17) 0.0357(9) Uani 1 1 d . H10A H -0.540807 -0.755804 -0.813244 0.043 Uiso 1 1 calc R H10B H -0.531697 -0.771824 -0.732103 0.043 Uiso 1 1 calc R C1 C 0.0438(7) -0.7722(5) -1.04148(19) 0.0578(14) Uani 1 1 d . H1A H -0.038901 -0.828215 -1.054535 0.087 Uiso 1 1 calc GR H1B H 0.153023 -0.792335 -1.060325 0.087 Uiso 1 1 calc GR H1C H 0.009851 -0.699697 -1.059404 0.087 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 0.0190(5) 0.0643(7) 0.0215(4) -0.0055(5) -0.0009(3) -0.0005(5) O1 0.0333(18) 0.088(3) 0.0367(16) -0.0252(17) 0.0045(14) -0.0291(17) O2 0.0308(17) 0.100(3) 0.0301(15) 0.0166(17) 0.0005(14) 0.0249(19) N1 0.0184(14) 0.0334(17) 0.0224(13) -0.0052(15) 0.0022(11) 0.0010(14) C19 0.030(2) 0.0247(19) 0.0226(16) 0.0017(16) -0.0001(15) 0.0003(17) C16 0.030(2) 0.0242(19) 0.0211(16) 0.0000(16) 0.0013(16) -0.0023(16) C6 0.044(3) 0.0236(19) 0.033(2) -0.0054(18) 0.012(2) -0.0062(19) C18 0.028(2) 0.0242(18) 0.0271(17) -0.0025(16) 0.0016(16) 0.0013(17) C17 0.036(2) 0.0262(19) 0.0205(16) -0.0025(15) 0.0043(17) 0.0031(18) C14 0.030(2) 0.0180(17) 0.0221(17) -0.0009(15) 0.0033(15) -0.0023(16) C7 0.063(3) 0.034(2) 0.036(2) 0.010(2) 0.018(2) 0.007(2) C15 0.0215(19) 0.0249(18) 0.0255(17) -0.0025(16) 0.0027(15) 0.0002(16) C5 0.0189(17) 0.038(2) 0.0210(15) -0.0045(18) 0.0029(13) 0.000(2) C2 0.037(2) 0.045(2) 0.0269(17) -0.001(2) 0.0079(16) 0.000(2) C4 0.049(3) 0.041(2) 0.0312(19) 0.0068(19) 0.0104(19) 0.019(2) C8 0.033(2) 0.028(2) 0.0260(18) -0.0038(17) 0.0049(18) 0.0001(17) C11 0.035(2) 0.038(2) 0.0194(16) 0.0031(17) 0.0036(17) 0.0088(19) C21 0.035(2) 0.036(2) 0.0237(18) -0.0012(17) -0.0035(17) 0.0020(18) C9 0.034(2) 0.039(2) 0.0264(19) -0.0097(18) 0.0018(17) -0.0080(19) C13 0.047(3) 0.033(2) 0.031(2) -0.0010(19) 0.0036(19) -0.005(2) C20 0.030(2) 0.053(3) 0.033(2) -0.008(2) 0.0024(18) 0.009(2) C12 0.031(2) 0.0266(19) 0.0231(18) -0.0017(17) 0.0019(16) -0.0005(17) C3 0.065(3) 0.033(2) 0.031(2) -0.0021(19) 0.015(2) 0.007(2) C10 0.0236(19) 0.061(3) 0.0226(16) -0.005(2) -0.0015(14) 0.000(2) C1 0.072(3) 0.077(4) 0.0248(19) 0.005(2) 0.009(2) 0.008(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 107.25(19) O1 S1 C5 107.75(19) O2 S1 O1 119.6(2) O2 S1 N1 107.7(2) O2 S1 C5 107.18(18) N1 S1 C5 106.75(15) C8 N1 S1 117.2(3) C12 N1 S1 119.8(3) C12 N1 C8 118.3(3) C18 C19 H19 119.4 C14 C19 H19 119.4 C14 C19 C18 121.2(3) C17 C16 C21 119.6(3) C15 C16 C17 118.5(3) C15 C16 C21 121.8(3) C7 C6 H6 120.2 C5 C6 H6 120.2 C5 C6 C7 119.5(4) C19 C18 C20 120.1(3) C17 C18 C19 118.7(3) C17 C18 C20 121.3(3) C16 C17 H17 119.3 C18 C17 C16 121.4(3) C18 C17 H17 119.3 C19 C14 C15 118.5(3) C19 C14 C12 122.0(3) C15 C14 C12 119.3(3) C6 C7 H7 119.6 C2 C7 C6 120.8(4) C2 C7 H7 119.6 C16 C15 C14 121.7(3) C16 C15 H15 119.1 C14 C15 H15 119.1 C6 C5 S1 119.7(3) C6 C5 C4 120.3(3) C4 C5 S1 119.8(3) C7 C2 C1 120.1(4) C3 C2 C7 119.1(3) C3 C2 C1 120.8(4) C5 C4 H4 120.5 C5 C4 C3 119.1(4) C3 C4 H4 120.5 N1 C8 H8 107.3 N1 C8 C9 110.7(3) N1 C8 C13 110.7(3) C9 C8 H8 107.3 C9 C8 C13 113.2(4) C13 C8 H8 107.3 H11A C11 H11B 107.8 C12 C11 H11A 109.0 C12 C11 H11B 109.0 C10 C11 H11A 109.0 C10 C11 H11B 109.0 C10 C11 C12 112.9(3) C16 C21 H21A 109.5 C16 C21 H21B 109.5 C16 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C8 C9 H9A 109.1 C8 C9 H9B 109.1 H9A C9 H9B 107.9 C10 C9 C8 112.3(3) C10 C9 H9A 109.1 C10 C9 H9B 109.1 C8 C13 H13A 109.5 C8 C13 H13B 109.5 C8 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C18 C20 H20A 109.5 C18 C20 H20B 109.5 C18 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 N1 C12 C14 110.2(3) N1 C12 C11 110.8(3) N1 C12 H12 106.4 C14 C12 H12 106.4 C11 C12 C14 116.1(3) C11 C12 H12 106.4 C2 C3 C4 121.1(4) C2 C3 H3 119.4 C4 C3 H3 119.4 C11 C10 C9 109.0(3) C11 C10 H10A 109.9 C11 C10 H10B 109.9 C9 C10 H10A 109.9 C9 C10 H10B 109.9 H10A C10 H10B 108.3 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 1.434(3) S1 O2 1.423(3) S1 N1 1.624(3) S1 C5 1.769(3) N1 C8 1.488(5) N1 C12 1.488(5) C19 H19 0.9500 C19 C18 1.400(5) C19 C14 1.389(5) C16 C17 1.399(5) C16 C15 1.385(5) C16 C21 1.511(5) C6 H6 0.9500 C6 C7 1.391(6) C6 C5 1.375(5) C18 C17 1.380(5) C18 C20 1.512(5) C17 H17 0.9500 C14 C15 1.390(5) C14 C12 1.536(5) C7 H7 0.9500 C7 C2 1.372(6) C15 H15 0.9500 C5 C4 1.380(6) C2 C3 1.370(6) C2 C1 1.524(5) C4 H4 0.9500 C4 C3 1.393(5) C8 H8 1.0000 C8 C9 1.521(6) C8 C13 1.524(5) C11 H11A 0.9900 C11 H11B 0.9900 C11 C12 1.522(5) C11 C10 1.515(6) C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C9 H9A 0.9900 C9 H9B 0.9900 C9 C10 1.517(6) C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 C12 H12 1.0000 C3 H3 0.9500 C10 H10A 0.9900 C10 H10B 0.9900 C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800