#------------------------------------------------------------------------------ #$Date: 2019-05-18 04:09:11 +0300 (Sat, 18 May 2019) $ #$Revision: 215288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123486.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_7123486 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 'C16 H20 N O2 S2' _chemical_formula_sum 'C16 H20 N O2 S2' _chemical_formula_weight 322.45 _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 2018-10-25 _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 10.6010(5) _cell_length_b 11.7414(5) _cell_length_c 12.8810(6) _cell_measurement_reflns_used 3732 _cell_measurement_temperature 150 _cell_measurement_theta_max 29.7400 _cell_measurement_theta_min 2.3570 _cell_volume 1603.31(13) _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 -108.00 19.00 0.50 6.00 -- -20.00 -72.00-180.00 254 2 \w -35.00 -5.00 0.50 6.00 -- -20.00 72.00 -36.00 60 ; _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 0.0405004000 _diffrn_orient_matrix_UB_12 0.0469037000 _diffrn_orient_matrix_UB_13 0.0097215000 _diffrn_orient_matrix_UB_21 -0.0508558000 _diffrn_orient_matrix_UB_22 0.0379953000 _diffrn_orient_matrix_UB_23 -0.0089578000 _diffrn_orient_matrix_UB_31 -0.0159339000 _diffrn_orient_matrix_UB_32 -0.0021423000 _diffrn_orient_matrix_UB_33 0.0534409000 _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 0.0440 _diffrn_reflns_av_unetI/netI 0.0611 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4842 _diffrn_reflns_point_group_measured_fraction_full 0.969 _diffrn_reflns_point_group_measured_fraction_max 0.969 _diffrn_reflns_theta_full 24.989 _diffrn_reflns_theta_max 24.989 _diffrn_reflns_theta_min 2.347 _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 0.336 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.73434 _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 1.336 _exptl_crystal_description block _exptl_crystal_F_000 684 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.201 _exptl_crystal_size_min 0.18 _refine_diff_density_max 1.249 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.197 _refine_ls_abs_structure_details ; Flack x determined using 899 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.07(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.212 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2741 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.218 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0622 _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^)+(0.1220P)^2^+0.9790P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1791 _refine_ls_wR_factor_ref 0.2092 _reflns_Friedel_coverage 0.681 _reflns_Friedel_fraction_full 0.927 _reflns_Friedel_fraction_max 0.927 _reflns_number_gt 2511 _reflns_number_total 2741 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc03127h2.cif _cod_data_source_block sjg-dsv-8-24_mo _cod_database_code 7123486 _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 0.942 _shelx_estimated_absorpt_t_min 0.933 _reflns_odcompleteness_completeness 90.34 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.11 _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. Uiso/Uaniso restraints and constraints Uanis(C14) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001 3.a Ternary CH refined with riding coordinates: N1(H1), C9(H9), C12(H12) 3.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C11(H11A,H11B) 3.c Aromatic/amide H refined with riding coordinates: C14(H14), C6(H6), C7(H7), C3(H3), C4(H4), C15(H15), C16(H16) 3.d Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL sjg-dsv-8-24_mo_a.res in P2(1)2(1)2(1) sjg-dsv-8-24_mo.res created by SHELXL-2018/3 at 13:19:14 on 25-Oct-2018 REM Old TITL sjg-dsv-8-24_mo_a.res in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.116, Rweak 0.025, Alpha 0.001 REM 0.519 for 20 systematic absences, Orientation as input REM Flack x = -1.378 ( 0.814 ) from 1049 Parsons' quotients REM Formula found by SHELXT: C16 N O2 S2 CELL 0.71073 10.601 11.7414 12.881 90 90 90 ZERR 4 0.0005 0.0005 0.0006 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 64 80 4 8 8 ISOR 0.001 0.001 C14 L.S. 100 PLAN 20 SIZE 0.18 0.201 0.21 TEMP -123.15 BOND list 4 fmap 2 acta OMIT -3 50 REM REM REM WGHT 0.122000 0.979000 FVAR 0.50995 S1 5 -0.766035 -0.542940 -0.340294 11.00000 0.01809 0.01794 = 0.02013 0.00236 0.00098 0.00087 S2 5 -0.303704 -0.569525 -0.244382 11.00000 0.03887 0.05286 = 0.05780 -0.01188 -0.00643 -0.00293 O1 4 -0.850806 -0.537472 -0.427022 11.00000 0.02292 0.02884 = 0.02021 0.00410 -0.00156 0.00331 O2 4 -0.712850 -0.439299 -0.299068 11.00000 0.02699 0.01577 = 0.03078 -0.00084 0.00005 -0.00151 C14 1 -0.401397 -0.520516 -0.429929 11.00000 0.00538 0.00674 = 0.01219 0.00205 0.00121 -0.00123 AFIX 43 H14 2 -0.454922 -0.514755 -0.488847 11.00000 -1.20000 AFIX 0 C2 1 -0.963851 -0.730020 -0.077194 11.00000 0.02207 0.02049 = 0.02523 -0.00088 0.00888 0.00127 C6 1 -0.945165 -0.685361 -0.258878 11.00000 0.02135 0.02573 = 0.01818 -0.00004 -0.00219 0.00203 AFIX 43 H6 2 -0.973653 -0.694432 -0.328314 11.00000 -1.20000 AFIX 0 N1 3 -0.647280 -0.622629 -0.376195 11.00000 0.01838 0.02080 = 0.01707 -0.00258 -0.00124 0.00147 AFIX 13 H1 2 -0.604093 -0.573309 -0.428566 11.00000 -1.20000 AFIX 0 C7 1 -1.004163 -0.743603 -0.179288 11.00000 0.01914 0.02302 = 0.03353 -0.00055 -0.00046 -0.00799 AFIX 43 H7 2 -1.072592 -0.793170 -0.194334 11.00000 -1.20000 AFIX 0 C3 1 -0.864625 -0.654548 -0.056778 11.00000 0.02640 0.02777 = 0.02121 -0.00272 0.00272 0.00109 AFIX 43 H3 2 -0.837481 -0.643665 0.012806 11.00000 -1.20000 AFIX 0 C4 1 -0.805297 -0.595491 -0.135911 11.00000 0.01685 0.02359 = 0.02128 -0.00234 0.00352 -0.00122 AFIX 43 H4 2 -0.739073 -0.543494 -0.121000 11.00000 -1.20000 AFIX 0 C9 1 -0.674347 -0.729560 -0.438053 11.00000 0.02479 0.01596 = 0.02317 -0.00387 0.00021 -0.00106 AFIX 13 H9 2 -0.753110 -0.766411 -0.411656 11.00000 -1.20000 AFIX 0 C8 1 -0.687592 -0.704776 -0.553956 11.00000 0.02667 0.03130 = 0.02502 -0.00438 0.00046 0.00013 AFIX 137 H8A 2 -0.764258 -0.660057 -0.566024 11.00000 -1.50000 H8B 2 -0.693012 -0.776721 -0.592267 11.00000 -1.50000 H8C 2 -0.614004 -0.661649 -0.577937 11.00000 -1.50000 AFIX 0 C10 1 -0.559080 -0.803767 -0.410250 11.00000 0.02665 0.01912 = 0.02972 -0.00037 -0.00140 0.00413 AFIX 23 H10A 2 -0.579579 -0.885727 -0.416657 11.00000 -1.20000 H10B 2 -0.486817 -0.786096 -0.456192 11.00000 -1.20000 AFIX 0 C12 1 -0.545078 -0.642292 -0.297987 11.00000 0.01442 0.02044 = 0.02484 0.00066 -0.00212 0.00035 AFIX 13 H12 2 -0.574163 -0.616956 -0.227840 11.00000 -1.20000 AFIX 0 C1 1 -1.026623 -0.792207 0.011971 11.00000 0.03642 0.03651 = 0.03524 -0.00433 0.01597 -0.01457 AFIX 137 H1A 2 -1.081783 -0.739510 0.049656 11.00000 -1.50000 H1B 2 -0.961913 -0.821697 0.059188 11.00000 -1.50000 H1C 2 -1.076779 -0.855640 -0.015253 11.00000 -1.50000 AFIX 0 C13 1 -0.426912 -0.578767 -0.327769 11.00000 0.01678 0.02367 = 0.02597 -0.00302 0.00112 0.00619 C5 1 -0.844316 -0.613603 -0.237543 11.00000 0.01408 0.01615 = 0.01926 0.00183 0.00604 0.00366 C11 1 -0.529411 -0.773312 -0.299330 11.00000 0.02673 0.02124 = 0.03239 0.00691 0.00190 0.00314 AFIX 23 H11A 2 -0.442242 -0.795677 -0.280759 11.00000 -1.20000 H11B 2 -0.589086 -0.810360 -0.250806 11.00000 -1.20000 AFIX 0 C15 1 -0.271242 -0.474039 -0.415812 11.00000 0.03113 0.02746 = 0.07572 0.00963 0.01488 -0.00642 AFIX 43 H15 2 -0.230198 -0.432294 -0.469201 11.00000 -1.20000 AFIX 0 C16 1 -0.215628 -0.493794 -0.325195 11.00000 0.02089 0.03219 = 0.09495 -0.01545 0.00160 -0.00386 AFIX 43 H16 2 -0.133515 -0.467156 -0.308376 11.00000 -1.20000 AFIX 0 HKLF 4 REM sjg-dsv-8-24_mo_a.res in P2(1)2(1)2(1) REM wR2 = 0.2092, GooF = S = 1.212, Restrained GooF = 1.218 for all data REM R1 = 0.0622 for 2511 Fo > 4sig(Fo) and 0.0739 for all 2741 data REM 192 parameters refined using 6 restraints END WGHT 0.1312 1.3891 REM Highest difference peak 1.249, deepest hole -0.606, 1-sigma level 0.197 Q1 1 -0.4013 -0.5317 -0.4615 11.00000 0.05 1.25 Q2 1 -0.3966 -0.5199 -0.3977 11.00000 0.05 1.09 Q3 1 -0.9921 -0.7409 -0.0410 11.00000 0.05 0.57 Q4 1 -1.0053 -0.8841 0.0147 11.00000 0.05 0.53 Q5 1 -0.0325 -0.4581 -0.3634 11.00000 0.05 0.52 Q6 1 -0.0914 -0.5151 -0.3901 11.00000 0.05 0.49 Q7 1 -1.0273 -0.9164 -0.0535 11.00000 0.05 0.46 Q8 1 -0.5609 -0.9836 -0.5353 11.00000 0.05 0.45 Q9 1 -0.0304 -0.3866 -0.3776 11.00000 0.05 0.45 Q10 1 -0.9835 -0.5148 -0.4533 11.00000 0.05 0.44 Q11 1 -1.0357 -0.6029 -0.3382 11.00000 0.05 0.43 Q12 1 -1.0053 -0.7802 0.0745 11.00000 0.05 0.43 Q13 1 -0.9926 -0.9259 0.0795 11.00000 0.05 0.43 Q14 1 -0.9816 -0.7628 -0.1317 11.00000 0.05 0.40 Q15 1 -0.5408 -0.6285 -0.6550 11.00000 0.05 0.40 Q16 1 -0.0026 -0.4199 -0.2964 11.00000 0.05 0.40 Q17 1 -0.9761 -0.6991 -0.3009 11.00000 0.05 0.40 Q18 1 -0.9422 -0.9230 -0.0651 11.00000 0.05 0.39 Q19 1 -1.0620 -0.8000 0.0048 11.00000 0.05 0.39 Q20 1 -1.0698 -0.8666 -0.2237 11.00000 0.05 0.38 ; _shelx_res_checksum 5449 _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 1.461 _oxdiff_exptl_absorpt_empirical_full_min 0.825 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 _atom_site_refinement_flags_adp S1 S -0.76604(15) -0.54294(13) -0.34029(12) 0.0187(5) Uani 1 1 d . . S2 S -0.3037(2) -0.5695(2) -0.2444(2) 0.0498(7) Uani 1 1 d . . O1 O -0.8508(4) -0.5375(4) -0.4270(3) 0.0240(11) Uani 1 1 d . . O2 O -0.7128(5) -0.4393(4) -0.2991(4) 0.0245(11) Uani 1 1 d . . C14 C -0.4014(5) -0.5205(4) -0.4299(4) 0.0081(11) Uani 1 1 d . U H14 H -0.454922 -0.514755 -0.488847 0.010 Uiso 1 1 calc R . C2 C -0.9639(7) -0.7300(6) -0.0772(6) 0.0226(15) Uani 1 1 d . . C6 C -0.9452(6) -0.6854(6) -0.2589(5) 0.0218(14) Uani 1 1 d . . H6 H -0.973653 -0.694432 -0.328314 0.026 Uiso 1 1 calc R . N1 N -0.6473(5) -0.6226(5) -0.3762(4) 0.0188(12) Uani 1 1 d . . H1 H -0.604093 -0.573309 -0.428566 0.023 Uiso 1 1 calc R . C7 C -1.0042(7) -0.7436(6) -0.1793(6) 0.0252(16) Uani 1 1 d . . H7 H -1.072592 -0.793170 -0.194334 0.030 Uiso 1 1 calc R . C3 C -0.8646(7) -0.6545(6) -0.0568(5) 0.0251(16) Uani 1 1 d . . H3 H -0.837481 -0.643665 0.012806 0.030 Uiso 1 1 calc R . C4 C -0.8053(6) -0.5955(6) -0.1359(5) 0.0206(14) Uani 1 1 d . . H4 H -0.739073 -0.543494 -0.121000 0.025 Uiso 1 1 calc R . C9 C -0.6743(7) -0.7296(5) -0.4381(5) 0.0213(15) Uani 1 1 d . . H9 H -0.753110 -0.766411 -0.411656 0.026 Uiso 1 1 calc R . C8 C -0.6876(7) -0.7048(7) -0.5540(5) 0.0277(16) Uani 1 1 d . . H8A H -0.764258 -0.660057 -0.566024 0.041 Uiso 1 1 calc GR . H8B H -0.693012 -0.776721 -0.592267 0.041 Uiso 1 1 calc GR . H8C H -0.614004 -0.661649 -0.577937 0.041 Uiso 1 1 calc GR . C10 C -0.5591(7) -0.8038(6) -0.4103(6) 0.0252(16) Uani 1 1 d . . H10A H -0.579579 -0.885727 -0.416657 0.030 Uiso 1 1 calc R . H10B H -0.486817 -0.786096 -0.456192 0.030 Uiso 1 1 calc R . C12 C -0.5451(6) -0.6423(6) -0.2980(5) 0.0199(15) Uani 1 1 d . . H12 H -0.574163 -0.616956 -0.227840 0.024 Uiso 1 1 calc R . C1 C -1.0266(8) -0.7922(7) 0.0120(6) 0.0361(19) Uani 1 1 d . . H1A H -1.081783 -0.739510 0.049656 0.054 Uiso 1 1 calc GR . H1B H -0.961913 -0.821697 0.059188 0.054 Uiso 1 1 calc GR . H1C H -1.076779 -0.855640 -0.015253 0.054 Uiso 1 1 calc GR . C13 C -0.4269(6) -0.5788(6) -0.3278(5) 0.0221(15) Uani 1 1 d . . C5 C -0.8443(6) -0.6136(5) -0.2375(5) 0.0165(13) Uani 1 1 d . . C11 C -0.5294(7) -0.7733(6) -0.2993(5) 0.0268(17) Uani 1 1 d . . H11A H -0.442242 -0.795677 -0.280759 0.032 Uiso 1 1 calc R . H11B H -0.589086 -0.810360 -0.250806 0.032 Uiso 1 1 calc R . C15 C -0.2712(8) -0.4740(7) -0.4158(8) 0.045(2) Uani 1 1 d . . H15 H -0.230198 -0.432294 -0.469201 0.054 Uiso 1 1 calc R . C16 C -0.2156(8) -0.4938(7) -0.3252(9) 0.049(3) Uani 1 1 d . . H16 H -0.133515 -0.467156 -0.308376 0.059 Uiso 1 1 calc R . 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 0.0181(8) 0.0179(8) 0.0201(8) 0.0024(6) 0.0010(7) 0.0009(7) S2 0.0389(12) 0.0529(14) 0.0578(15) -0.0119(12) -0.0064(11) -0.0029(10) O1 0.023(2) 0.029(2) 0.020(2) 0.004(2) -0.002(2) 0.003(2) O2 0.027(3) 0.016(2) 0.031(3) -0.0008(19) 0.000(2) -0.002(2) C14 0.0054(15) 0.0067(15) 0.0122(15) 0.0020(12) 0.0012(12) -0.0012(12) C2 0.022(4) 0.020(3) 0.025(4) -0.001(3) 0.009(3) 0.001(3) C6 0.021(3) 0.026(3) 0.018(3) 0.000(3) -0.002(3) 0.002(3) N1 0.018(3) 0.021(3) 0.017(3) -0.003(2) -0.001(2) 0.001(2) C7 0.019(3) 0.023(3) 0.034(4) -0.001(3) 0.000(3) -0.008(3) C3 0.026(4) 0.028(4) 0.021(3) -0.003(3) 0.003(3) 0.001(3) C4 0.017(3) 0.024(3) 0.021(3) -0.002(3) 0.004(3) -0.001(3) C9 0.025(4) 0.016(3) 0.023(3) -0.004(3) 0.000(3) -0.001(3) C8 0.027(4) 0.031(4) 0.025(4) -0.004(3) 0.000(3) 0.000(3) C10 0.027(4) 0.019(3) 0.030(4) 0.000(3) -0.001(3) 0.004(3) C12 0.014(3) 0.020(3) 0.025(3) 0.001(3) -0.002(3) 0.000(3) C1 0.036(4) 0.037(4) 0.035(4) -0.004(4) 0.016(4) -0.015(4) C13 0.017(3) 0.024(3) 0.026(3) -0.003(3) 0.001(3) 0.006(3) C5 0.014(3) 0.016(3) 0.019(3) 0.002(3) 0.006(3) 0.004(3) C11 0.027(4) 0.021(3) 0.032(4) 0.007(3) 0.002(3) 0.003(3) C15 0.031(4) 0.027(4) 0.076(6) 0.010(4) 0.015(5) -0.006(4) C16 0.021(4) 0.032(4) 0.095(8) -0.015(5) 0.002(5) -0.004(4) 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 O2 119.6(3) O1 S1 N1 106.7(3) O1 S1 C5 108.0(3) O2 S1 N1 106.6(3) O2 S1 C5 107.7(3) N1 S1 C5 107.7(3) C16 S2 C13 94.0(4) C15 C14 C13 103.0(6) C7 C2 C3 118.7(6) C7 C2 C1 121.7(7) C3 C2 C1 119.5(7) C7 C6 C5 120.1(6) C9 N1 S1 118.5(5) C12 N1 S1 117.1(4) C12 N1 C9 111.3(5) C6 C7 C2 120.3(6) C4 C3 C2 121.3(7) C3 C4 C5 118.8(6) N1 C9 C8 111.9(6) N1 C9 C10 101.3(5) C8 C9 C10 114.0(6) C11 C10 C9 104.6(6) N1 C12 C13 110.7(5) N1 C12 C11 102.9(5) C13 C12 C11 113.6(6) C14 C13 S2 112.7(5) C14 C13 C12 126.6(6) C12 C13 S2 120.7(5) C6 C5 S1 119.8(5) C6 C5 C4 120.6(6) C4 C5 S1 119.6(5) C10 C11 C12 103.0(6) C16 C15 C14 116.9(7) C15 C16 S2 113.3(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.435(5) S1 O2 1.442(5) S1 N1 1.635(6) S1 C5 1.769(6) S2 C13 1.695(7) S2 C16 1.657(10) C14 C13 1.508(8) C14 C15 1.495(10) C2 C7 1.392(10) C2 C3 1.400(10) C2 C1 1.515(10) C6 C7 1.382(10) C6 C5 1.389(9) N1 C9 1.514(8) N1 C12 1.497(8) C3 C4 1.384(9) C4 C5 1.389(9) C9 C8 1.528(9) C9 C10 1.543(10) C10 C11 1.506(10) C12 C13 1.508(9) C12 C11 1.547(9) C15 C16 1.328(13)