#------------------------------------------------------------------------------ #$Date: 2019-05-18 04:09:11 +0300 (Sat, 18 May 2019) $ #$Revision: 215288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123491.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_7123491 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 'C25 H27 N O2 S' _chemical_formula_sum 'C25 H27 N O2 S' _chemical_formula_weight 405.53 _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 direct _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 9.2849(3) _cell_length_b 11.8237(3) _cell_length_c 19.1053(5) _cell_measurement_reflns_used 9231 _cell_measurement_temperature 150 _cell_measurement_theta_max 31.0550 _cell_measurement_theta_min 2.0480 _cell_volume 2097.42(10) _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 70.00 0.50 8.00 -- -20.00 0.00 -36.00 360 2 \w -20.00 54.00 0.50 8.00 -- -20.00 72.00 -36.00 148 ; _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 0.0484482000 _diffrn_orient_matrix_UB_12 0.0277401000 _diffrn_orient_matrix_UB_13 -0.0229823000 _diffrn_orient_matrix_UB_21 -0.0230226000 _diffrn_orient_matrix_UB_22 -0.0353567000 _diffrn_orient_matrix_UB_23 -0.0278163000 _diffrn_orient_matrix_UB_31 -0.0544023000 _diffrn_orient_matrix_UB_32 0.0397538000 _diffrn_orient_matrix_UB_33 -0.0087015000 _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 0.0499 _diffrn_reflns_av_unetI/netI 0.0483 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9922 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 24.998 _diffrn_reflns_theta_max 24.998 _diffrn_reflns_theta_min 2.132 _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 0.176 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.40824 _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 1.284 _exptl_crystal_description block _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.281 _exptl_crystal_size_mid 0.275 _exptl_crystal_size_min 0.266 _refine_diff_density_max 0.233 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.062 _refine_ls_abs_structure_details ; Flack x determined using 1372 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 3654 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0355 _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^)+(0.0422P)^2^+0.3755P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0823 _refine_ls_wR_factor_ref 0.0847 _reflns_Friedel_coverage 0.738 _reflns_Friedel_fraction_full 0.989 _reflns_Friedel_fraction_max 0.989 _reflns_number_gt 3451 _reflns_number_total 3654 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc03127h2.cif _cod_data_source_block sjg-rp-03-235_mo _cod_original_cell_volume 2097.41(10) _cod_database_code 7123491 _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. ; _reflns_odcompleteness_completeness 93.03 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.06 _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: C9(H9A,H9B), C10(H10A,H10B), C7(H7A,H7B), C11(H11A,H11B) 2.c Aromatic/amide H refined with riding coordinates: C21(H21), C20(H20), C5(H5), C1(H1), C24(H24), C23(H23), C2(H2), C17(H17), C4(H4), C18(H18), C16(H16), C3(H3), C14(H14), C15(H15) 2.d Idealised Me refined as rotating group: C25(H25A,H25B,H25C) ; _shelx_res_file ; TITL sjg-rp-03-235_mo_a.res in P2(1)2(1)2(1) sjg-rp-03-235_mo.res created by SHELXL-2018/3 at 17:06:14 on 18-Oct-2018 REM Old TITL SJG-RP-03-235_Mo in P212121 #19 REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.187, Rweak 0.047, Alpha 0.004, Orientation as input REM Flack x = -7.334 ( 2.119 ) from Parsons' quotients REM Formula found by SHELXT: C24 N2 O1 Cl CELL 0.71073 9.284879 11.823657 19.105332 90 90 90 ZERR 4 0.000287 0.00032 0.000545 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 100 108 4 8 4 L.S. 4 0 0 PLAN 20 TEMP -123.15 BOND $H LIST 6 MORE -1 CONF fmap 2 53 acta 52 OMIT -3 50 OMIT -1 3 1 OMIT 0 2 0 OMIT 0 1 1 OMIT 1 1 2 OMIT -2 4 1 OMIT 0 2 1 OMIT 0 1 3 OMIT 1 0 2 OMIT 1 0 1 OMIT 0 1 2 OMIT 1 0 3 OMIT 1 1 0 OMIT -1 1 1 REM REM REM WGHT 0.042200 0.375500 FVAR 4.68589 S1 5 0.707856 0.763391 0.149604 11.00000 0.02074 0.02303 = 0.02988 0.00152 -0.00098 -0.00077 O1 4 0.727316 0.814742 0.082296 11.00000 0.02426 0.03023 = 0.03869 0.01017 0.00369 -0.00140 O2 4 0.748082 0.824578 0.211275 11.00000 0.03012 0.02712 = 0.04267 -0.00666 -0.00803 -0.00053 C21 1 0.926173 0.488346 0.214091 11.00000 0.03114 0.03551 = 0.02297 0.00217 -0.00500 0.00418 AFIX 43 H21 2 0.962180 0.459429 0.257056 11.00000 -1.20000 AFIX 0 N1 3 0.538205 0.730819 0.156129 11.00000 0.02085 0.02634 = 0.02140 0.00310 -0.00019 0.00048 C20 1 0.857777 0.592300 0.213120 11.00000 0.02841 0.02993 = 0.02674 -0.00524 -0.00423 0.00093 AFIX 43 H20 2 0.846904 0.634272 0.255190 11.00000 -1.20000 AFIX 0 C6 1 0.355408 0.714172 0.334807 11.00000 0.02162 0.02335 = 0.02706 0.00052 0.00325 0.00511 C22 1 0.943005 0.425437 0.152931 11.00000 0.02102 0.02585 = 0.02848 0.00077 -0.00147 -0.00171 C19 1 0.805321 0.634894 0.150764 11.00000 0.01615 0.02624 = 0.02800 0.00209 -0.00168 -0.00110 C5 1 0.428360 0.773040 0.386745 11.00000 0.04257 0.02667 = 0.02996 0.00081 0.00140 -0.00741 AFIX 43 H5 2 0.489844 0.833842 0.373947 11.00000 -1.20000 AFIX 0 C1 1 0.267812 0.624332 0.355171 11.00000 0.02512 0.03082 = 0.03173 -0.00263 -0.00183 -0.00036 AFIX 43 H1 2 0.216914 0.582516 0.320661 11.00000 -1.20000 AFIX 0 C9 1 0.446586 0.554236 0.207926 11.00000 0.03276 0.02318 = 0.03037 0.00400 0.00772 0.00264 AFIX 23 H9A 2 0.532597 0.510344 0.193784 11.00000 -1.20000 H9B 2 0.407636 0.520015 0.251265 11.00000 -1.20000 AFIX 0 C24 1 0.820726 0.573593 0.089016 11.00000 0.03027 0.03867 = 0.02195 0.00382 -0.00022 0.00918 AFIX 43 H24 2 0.784216 0.602539 0.046158 11.00000 -1.20000 AFIX 0 C25 1 1.016806 0.312188 0.155261 11.00000 0.03053 0.02744 = 0.03578 0.00294 -0.00201 0.00177 AFIX 137 H25A 2 1.121070 0.323258 0.159349 11.00000 -1.50000 H25B 2 0.995548 0.270285 0.112227 11.00000 -1.50000 H25C 2 0.981862 0.269270 0.195724 11.00000 -1.50000 AFIX 0 C10 1 0.333601 0.547483 0.150350 11.00000 0.03450 0.01964 = 0.03760 -0.00296 0.00572 -0.00457 AFIX 23 H10A 2 0.308228 0.467378 0.141664 11.00000 -1.20000 H10B 2 0.245349 0.587687 0.165402 11.00000 -1.20000 AFIX 0 C23 1 0.889519 0.470509 0.090824 11.00000 0.03568 0.03725 = 0.02181 -0.00335 -0.00083 0.00647 AFIX 43 H23 2 0.900799 0.429032 0.048592 11.00000 -1.20000 AFIX 0 C2 1 0.253903 0.595065 0.425337 11.00000 0.02655 0.03210 = 0.03561 0.00895 0.00601 0.00037 AFIX 43 H2 2 0.194864 0.532912 0.438366 11.00000 -1.20000 AFIX 0 C7 1 0.373112 0.747266 0.258889 11.00000 0.03062 0.02181 = 0.02439 0.00225 0.00044 0.00224 AFIX 23 H7A 2 0.399024 0.828354 0.256019 11.00000 -1.20000 H7B 2 0.280390 0.736609 0.234168 11.00000 -1.20000 AFIX 0 C17 1 0.282224 1.016097 0.102592 11.00000 0.03521 0.02564 = 0.03318 0.00071 0.00035 0.00097 AFIX 43 H17 2 0.316049 1.091508 0.107513 11.00000 -1.20000 AFIX 0 C4 1 0.413571 0.745202 0.456646 11.00000 0.05634 0.03749 = 0.02678 -0.00185 -0.00456 -0.00917 AFIX 43 H4 2 0.463735 0.787224 0.491314 11.00000 -1.20000 AFIX 0 C18 1 0.378472 0.926816 0.103070 11.00000 0.02260 0.03152 = 0.02663 0.00252 -0.00208 -0.00188 AFIX 43 H18 2 0.478340 0.941540 0.108894 11.00000 -1.20000 AFIX 0 C8 1 0.490349 0.676394 0.222525 11.00000 0.02472 0.02435 = 0.02217 0.00374 -0.00107 0.00121 AFIX 13 H8 2 0.575460 0.674137 0.254569 11.00000 -1.20000 AFIX 0 C13 1 0.331399 0.815565 0.095149 11.00000 0.02451 0.02797 = 0.01540 0.00224 -0.00010 -0.00128 C16 1 0.136023 0.995055 0.094892 11.00000 0.03060 0.03628 = 0.02990 0.00437 0.00160 0.01129 AFIX 43 H16 2 0.069394 1.056031 0.094990 11.00000 -1.20000 AFIX 0 C12 1 0.445380 0.722387 0.093290 11.00000 0.02164 0.02918 = 0.01892 -0.00011 0.00158 0.00014 AFIX 13 H12 2 0.508571 0.739159 0.052194 11.00000 -1.20000 AFIX 0 C3 1 0.325635 0.656069 0.476092 11.00000 0.04357 0.04411 = 0.02536 0.00743 0.00493 0.00325 AFIX 43 H3 2 0.314721 0.636993 0.524102 11.00000 -1.20000 AFIX 0 C11 1 0.390662 0.600425 0.083283 11.00000 0.02899 0.02958 = 0.03093 -0.00719 0.00111 0.00019 AFIX 23 H11A 2 0.313027 0.600509 0.047764 11.00000 -1.20000 H11B 2 0.470416 0.553251 0.065102 11.00000 -1.20000 AFIX 0 C14 1 0.184393 0.795898 0.086816 11.00000 0.02640 0.03003 = 0.02433 0.00402 -0.00031 -0.00500 AFIX 43 H14 2 0.150186 0.720778 0.080909 11.00000 -1.20000 AFIX 0 C15 1 0.087588 0.885475 0.087095 11.00000 0.01901 0.04568 = 0.02960 0.00561 -0.00003 0.00165 AFIX 43 H15 2 -0.012529 0.871195 0.081888 11.00000 -1.20000 AFIX 0 HKLF 4 REM sjg-rp-03-235_mo_a.res in P2(1)2(1)2(1) REM wR2 = 0.0847, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0355 for 3451 Fo > 4sig(Fo) and 0.0389 for all 3654 data REM 263 parameters refined using 0 restraints END WGHT 0.0422 0.3755 REM Highest difference peak 0.233, deepest hole -0.331, 1-sigma level 0.062 Q1 1 0.5351 0.7729 0.4823 11.00000 0.05 0.23 Q2 1 0.4152 0.8396 0.5036 11.00000 0.05 0.21 Q3 1 0.5199 0.7378 0.5131 11.00000 0.05 0.20 Q4 1 0.5346 0.8437 0.4956 11.00000 0.05 0.19 Q5 1 0.3225 0.7174 0.4798 11.00000 0.05 0.19 Q6 1 0.6913 0.7058 0.0173 11.00000 0.05 0.18 Q7 1 0.4614 0.6153 0.2198 11.00000 0.05 0.17 Q8 1 0.1039 0.5796 0.4839 11.00000 0.05 0.17 Q9 1 0.3811 0.6203 0.0125 11.00000 0.05 0.17 Q10 1 0.4175 0.5464 0.0043 11.00000 0.05 0.17 Q11 1 0.7873 0.7415 0.0038 11.00000 0.05 0.17 Q12 1 0.0770 0.5675 0.5083 11.00000 0.05 0.17 Q13 1 0.0424 1.0817 0.0190 11.00000 0.05 0.17 Q14 1 0.3630 0.7712 0.5224 11.00000 0.05 0.17 Q15 1 0.1214 0.5399 0.0036 11.00000 0.05 0.17 Q16 1 0.0021 0.9599 0.0205 11.00000 0.05 0.17 Q17 1 0.6032 0.7777 0.0012 11.00000 0.05 0.17 Q18 1 0.5585 0.7979 0.0153 11.00000 0.05 0.17 Q19 1 0.2326 0.6669 0.5177 11.00000 0.05 0.17 Q20 1 0.4608 0.4639 0.0192 11.00000 0.05 0.16 ; _shelx_res_checksum 52073 _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 1.702 _oxdiff_exptl_absorpt_empirical_full_min 0.685 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 0.70786(7) 0.76339(5) 0.14960(4) 0.02455(18) Uani 1 1 d . O1 O 0.7273(2) 0.81474(15) 0.08230(11) 0.0311(5) Uani 1 1 d . O2 O 0.7481(2) 0.82458(16) 0.21128(11) 0.0333(5) Uani 1 1 d . C21 C 0.9262(3) 0.4883(2) 0.21409(15) 0.0299(6) Uani 1 1 d . H21 H 0.962180 0.459429 0.257056 0.036 Uiso 1 1 calc R N1 N 0.5382(2) 0.73082(18) 0.15613(11) 0.0229(5) Uani 1 1 d . C20 C 0.8578(3) 0.5923(2) 0.21312(15) 0.0284(6) Uani 1 1 d . H20 H 0.846904 0.634272 0.255190 0.034 Uiso 1 1 calc R C6 C 0.3554(3) 0.7142(2) 0.33481(14) 0.0240(6) Uani 1 1 d . C22 C 0.9430(3) 0.4254(2) 0.15293(15) 0.0251(6) Uani 1 1 d . C19 C 0.8053(3) 0.6349(2) 0.15076(14) 0.0235(6) Uani 1 1 d . C5 C 0.4284(3) 0.7730(2) 0.38675(14) 0.0331(7) Uani 1 1 d . H5 H 0.489844 0.833842 0.373947 0.040 Uiso 1 1 calc R C1 C 0.2678(3) 0.6243(2) 0.35517(15) 0.0292(6) Uani 1 1 d . H1 H 0.216914 0.582516 0.320661 0.035 Uiso 1 1 calc R C9 C 0.4466(3) 0.5542(2) 0.20793(14) 0.0288(6) Uani 1 1 d . H9A H 0.532597 0.510344 0.193784 0.035 Uiso 1 1 calc R H9B H 0.407636 0.520015 0.251265 0.035 Uiso 1 1 calc R C24 C 0.8207(3) 0.5736(2) 0.08902(15) 0.0303(7) Uani 1 1 d . H24 H 0.784216 0.602539 0.046158 0.036 Uiso 1 1 calc R C25 C 1.0168(3) 0.3122(2) 0.15526(17) 0.0313(6) Uani 1 1 d . H25A H 1.121070 0.323258 0.159349 0.047 Uiso 1 1 calc GR H25B H 0.995548 0.270285 0.112227 0.047 Uiso 1 1 calc GR H25C H 0.981862 0.269270 0.195724 0.047 Uiso 1 1 calc GR C10 C 0.3336(3) 0.5475(2) 0.15035(16) 0.0306(6) Uani 1 1 d . H10A H 0.308228 0.467378 0.141664 0.037 Uiso 1 1 calc R H10B H 0.245349 0.587687 0.165402 0.037 Uiso 1 1 calc R C23 C 0.8895(3) 0.4705(2) 0.09082(15) 0.0316(7) Uani 1 1 d . H23 H 0.900799 0.429032 0.048592 0.038 Uiso 1 1 calc R C2 C 0.2539(3) 0.5951(2) 0.42534(16) 0.0314(7) Uani 1 1 d . H2 H 0.194864 0.532912 0.438366 0.038 Uiso 1 1 calc R C7 C 0.3731(3) 0.7473(2) 0.25889(14) 0.0256(6) Uani 1 1 d . H7A H 0.399024 0.828354 0.256019 0.031 Uiso 1 1 calc R H7B H 0.280390 0.736609 0.234168 0.031 Uiso 1 1 calc R C17 C 0.2822(3) 1.0161(2) 0.10259(16) 0.0313(7) Uani 1 1 d . H17 H 0.316049 1.091508 0.107513 0.038 Uiso 1 1 calc R C4 C 0.4136(4) 0.7452(3) 0.45665(15) 0.0402(8) Uani 1 1 d . H4 H 0.463735 0.787224 0.491314 0.048 Uiso 1 1 calc R C18 C 0.3785(3) 0.9268(2) 0.10307(14) 0.0269(6) Uani 1 1 d . H18 H 0.478340 0.941540 0.108894 0.032 Uiso 1 1 calc R C8 C 0.4903(3) 0.6764(2) 0.22252(14) 0.0237(6) Uani 1 1 d . H8 H 0.575460 0.674137 0.254569 0.028 Uiso 1 1 calc R C13 C 0.3314(3) 0.8156(2) 0.09515(13) 0.0226(6) Uani 1 1 d . C16 C 0.1360(3) 0.9951(3) 0.09489(15) 0.0323(7) Uani 1 1 d . H16 H 0.069394 1.056031 0.094990 0.039 Uiso 1 1 calc R C12 C 0.4454(3) 0.7224(2) 0.09329(13) 0.0232(6) Uani 1 1 d . H12 H 0.508571 0.739159 0.052194 0.028 Uiso 1 1 calc R C3 C 0.3256(3) 0.6561(3) 0.47609(16) 0.0377(8) Uani 1 1 d . H3 H 0.314721 0.636993 0.524102 0.045 Uiso 1 1 calc R C11 C 0.3907(3) 0.6004(2) 0.08328(15) 0.0298(7) Uani 1 1 d . H11A H 0.313027 0.600509 0.047764 0.036 Uiso 1 1 calc R H11B H 0.470416 0.553251 0.065102 0.036 Uiso 1 1 calc R C14 C 0.1844(3) 0.7959(2) 0.08682(14) 0.0269(6) Uani 1 1 d . H14 H 0.150186 0.720778 0.080909 0.032 Uiso 1 1 calc R C15 C 0.0876(3) 0.8855(2) 0.08710(15) 0.0314(7) Uani 1 1 d . H15 H -0.012529 0.871195 0.081888 0.038 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 0.0207(3) 0.0230(3) 0.0299(4) 0.0015(3) -0.0010(3) -0.0008(3) O1 0.0243(10) 0.0302(10) 0.0387(12) 0.0102(8) 0.0037(9) -0.0014(9) O2 0.0301(11) 0.0271(9) 0.0427(12) -0.0067(9) -0.0080(9) -0.0005(9) C21 0.0311(16) 0.0355(15) 0.0230(14) 0.0022(12) -0.0050(13) 0.0042(13) N1 0.0209(11) 0.0263(11) 0.0214(11) 0.0031(9) -0.0002(9) 0.0005(9) C20 0.0284(15) 0.0299(15) 0.0267(15) -0.0052(11) -0.0042(13) 0.0009(13) C6 0.0216(13) 0.0234(13) 0.0271(14) 0.0005(11) 0.0032(11) 0.0051(11) C22 0.0210(13) 0.0258(13) 0.0285(14) 0.0008(12) -0.0015(13) -0.0017(11) C19 0.0162(12) 0.0262(13) 0.0280(14) 0.0021(12) -0.0017(13) -0.0011(11) C5 0.0426(17) 0.0267(14) 0.0300(15) 0.0008(12) 0.0014(14) -0.0074(14) C1 0.0251(15) 0.0308(14) 0.0317(15) -0.0026(12) -0.0018(13) -0.0004(12) C9 0.0328(16) 0.0232(13) 0.0304(15) 0.0040(11) 0.0077(13) 0.0026(13) C24 0.0303(16) 0.0387(15) 0.0220(14) 0.0038(12) -0.0002(12) 0.0092(13) C25 0.0305(15) 0.0274(14) 0.0358(16) 0.0029(13) -0.0020(13) 0.0018(12) C10 0.0345(16) 0.0196(13) 0.0376(16) -0.0030(12) 0.0057(14) -0.0046(11) C23 0.0357(17) 0.0373(16) 0.0218(14) -0.0034(12) -0.0008(13) 0.0065(14) C2 0.0265(16) 0.0321(15) 0.0356(17) 0.0089(12) 0.0060(13) 0.0004(13) C7 0.0306(14) 0.0218(13) 0.0244(14) 0.0023(11) 0.0004(11) 0.0022(12) C17 0.0352(17) 0.0256(14) 0.0332(16) 0.0007(12) 0.0003(15) 0.0010(14) C4 0.056(2) 0.0375(17) 0.0268(16) -0.0019(13) -0.0046(15) -0.0092(16) C18 0.0226(14) 0.0315(15) 0.0266(15) 0.0025(12) -0.0021(12) -0.0019(12) C8 0.0247(15) 0.0243(13) 0.0222(13) 0.0037(11) -0.0011(11) 0.0012(11) C13 0.0245(14) 0.0280(13) 0.0154(13) 0.0022(11) -0.0001(11) -0.0013(11) C16 0.0306(15) 0.0363(17) 0.0299(16) 0.0044(13) 0.0016(14) 0.0113(14) C12 0.0216(13) 0.0292(13) 0.0189(13) -0.0001(11) 0.0016(11) 0.0001(12) C3 0.044(2) 0.0441(18) 0.0254(15) 0.0074(13) 0.0049(14) 0.0033(15) C11 0.0290(16) 0.0296(15) 0.0309(16) -0.0072(12) 0.0011(13) 0.0002(12) C14 0.0264(14) 0.0300(14) 0.0243(14) 0.0040(11) -0.0003(12) -0.0050(12) C15 0.0190(14) 0.0457(18) 0.0296(16) 0.0056(13) 0.0000(12) 0.0017(13) 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 106.93(11) O1 S1 C19 108.09(12) O2 S1 O1 119.42(11) O2 S1 N1 108.01(12) O2 S1 C19 106.87(12) N1 S1 C19 106.93(12) C20 C21 H21 119.5 C20 C21 C22 120.9(3) C22 C21 H21 119.5 C8 N1 S1 117.15(17) C12 N1 S1 121.15(17) C12 N1 C8 119.2(2) C21 C20 H20 120.1 C19 C20 C21 119.8(2) C19 C20 H20 120.1 C5 C6 C1 117.9(3) C5 C6 C7 120.2(2) C1 C6 C7 121.9(2) C21 C22 C25 120.1(2) C23 C22 C21 118.0(2) C23 C22 C25 121.9(3) C20 C19 S1 120.3(2) C20 C19 C24 120.3(2) C24 C19 S1 119.3(2) C6 C5 H5 119.2 C4 C5 C6 121.5(3) C4 C5 H5 119.2 C6 C1 H1 119.6 C2 C1 C6 120.9(3) C2 C1 H1 119.6 H9A C9 H9B 108.0 C10 C9 H9A 109.3 C10 C9 H9B 109.3 C10 C9 C8 111.4(2) C8 C9 H9A 109.3 C8 C9 H9B 109.3 C19 C24 H24 120.4 C23 C24 C19 119.2(3) C23 C24 H24 120.4 C22 C25 H25A 109.5 C22 C25 H25B 109.5 C22 C25 H25C 109.5 H25A C25 H25B 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C9 C10 H10A 109.6 C9 C10 H10B 109.6 H10A C10 H10B 108.1 C11 C10 C9 110.3(2) C11 C10 H10A 109.6 C11 C10 H10B 109.6 C22 C23 H23 119.1 C24 C23 C22 121.7(3) C24 C23 H23 119.1 C1 C2 H2 119.9 C3 C2 C1 120.2(3) C3 C2 H2 119.9 C6 C7 H7A 109.3 C6 C7 H7B 109.3 C6 C7 C8 111.7(2) H7A C7 H7B 107.9 C8 C7 H7A 109.3 C8 C7 H7B 109.3 C18 C17 H17 120.1 C18 C17 C16 119.7(3) C16 C17 H17 120.1 C5 C4 H4 120.0 C5 C4 C3 120.0(3) C3 C4 H4 120.0 C17 C18 H18 119.4 C17 C18 C13 121.1(3) C13 C18 H18 119.4 N1 C8 C9 109.4(2) N1 C8 C7 111.1(2) N1 C8 H8 107.3 C9 C8 C7 114.2(2) C9 C8 H8 107.3 C7 C8 H8 107.3 C18 C13 C12 117.7(2) C14 C13 C18 118.5(3) C14 C13 C12 123.7(2) C17 C16 H16 120.0 C15 C16 C17 119.9(3) C15 C16 H16 120.0 N1 C12 C13 109.6(2) N1 C12 H12 106.4 N1 C12 C11 110.8(2) C13 C12 H12 106.4 C13 C12 C11 116.7(2) C11 C12 H12 106.4 C2 C3 C4 119.6(3) C2 C3 H3 120.2 C4 C3 H3 120.2 C10 C11 C12 113.3(2) C10 C11 H11A 108.9 C10 C11 H11B 108.9 C12 C11 H11A 108.9 C12 C11 H11B 108.9 H11A C11 H11B 107.7 C13 C14 H14 119.8 C15 C14 C13 120.4(3) C15 C14 H14 119.8 C16 C15 C14 120.4(3) C16 C15 H15 119.8 C14 C15 H15 119.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.434(2) S1 O2 1.432(2) S1 N1 1.626(2) S1 C19 1.769(3) C21 H21 0.9500 C21 C20 1.384(4) C21 C22 1.394(4) N1 C8 1.490(3) N1 C12 1.481(3) C20 H20 0.9500 C20 C19 1.382(4) C6 C5 1.388(4) C6 C1 1.393(4) C6 C7 1.511(4) C22 C25 1.505(4) C22 C23 1.392(4) C19 C24 1.392(4) C5 H5 0.9500 C5 C4 1.382(4) C1 H1 0.9500 C1 C2 1.390(4) C9 H9A 0.9900 C9 H9B 0.9900 C9 C10 1.522(4) C9 C8 1.526(4) C24 H24 0.9500 C24 C23 1.376(4) C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 C10 H10A 0.9900 C10 H10B 0.9900 C10 C11 1.521(4) C23 H23 0.9500 C2 H2 0.9500 C2 C3 1.380(4) C7 H7A 0.9900 C7 H7B 0.9900 C7 C8 1.539(4) C17 H17 0.9500 C17 C18 1.383(4) C17 C16 1.388(4) C4 H4 0.9500 C4 C3 1.384(4) C18 H18 0.9500 C18 C13 1.394(4) C8 H8 1.0000 C13 C12 1.528(4) C13 C14 1.394(4) C16 H16 0.9500 C16 C15 1.380(4) C12 H12 1.0000 C12 C11 1.541(4) C3 H3 0.9500 C11 H11A 0.9900 C11 H11B 0.9900 C14 H14 0.9500 C14 C15 1.389(4) C15 H15 0.9500 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion S1 N1 C8 C9 -112.1(2) S1 N1 C8 C7 120.9(2) S1 N1 C12 C13 -114.0(2) S1 N1 C12 C11 115.8(2) S1 C19 C24 C23 -176.3(2) O1 S1 N1 C8 -179.57(18) O1 S1 N1 C12 18.6(2) O1 S1 C19 C20 152.3(2) O1 S1 C19 C24 -31.8(3) O2 S1 N1 C8 -49.9(2) O2 S1 N1 C12 148.32(19) O2 S1 C19 C20 22.5(3) O2 S1 C19 C24 -161.5(2) C21 C20 C19 S1 176.0(2) C21 C20 C19 C24 0.1(4) C21 C22 C23 C24 -0.5(4) N1 S1 C19 C20 -92.9(2) N1 S1 C19 C24 83.0(2) N1 C12 C11 C10 46.3(3) C20 C21 C22 C25 -179.6(3) C20 C21 C22 C23 0.3(4) C20 C19 C24 C23 -0.4(4) C6 C5 C4 C3 0.7(5) C6 C1 C2 C3 0.9(4) C6 C7 C8 N1 -162.8(2) C6 C7 C8 C9 72.9(3) C22 C21 C20 C19 -0.1(4) C19 S1 N1 C8 64.8(2) C19 S1 N1 C12 -97.0(2) C19 C24 C23 C22 0.6(4) C5 C6 C1 C2 0.2(4) C5 C6 C7 C8 94.6(3) C5 C4 C3 C2 0.4(5) C1 C6 C5 C4 -1.0(4) C1 C6 C7 C8 -84.8(3) C1 C2 C3 C4 -1.2(4) C9 C10 C11 C12 -54.3(3) C25 C22 C23 C24 179.3(3) C10 C9 C8 N1 -54.6(3) C10 C9 C8 C7 70.6(3) C7 C6 C5 C4 179.6(3) C7 C6 C1 C2 179.6(2) C17 C18 C13 C12 177.6(2) C17 C18 C13 C14 -0.1(4) C17 C16 C15 C14 -0.1(4) C18 C17 C16 C15 -0.6(5) C18 C13 C12 N1 54.0(3) C18 C13 C12 C11 -179.0(2) C18 C13 C14 C15 -0.6(4) C8 N1 C12 C13 84.5(3) C8 N1 C12 C11 -45.7(3) C8 C9 C10 C11 58.6(3) C13 C12 C11 C10 -80.1(3) C13 C14 C15 C16 0.7(4) C16 C17 C18 C13 0.7(4) C12 N1 C8 C9 50.0(3) C12 N1 C8 C7 -76.9(3) C12 C13 C14 C15 -178.1(2) C14 C13 C12 N1 -128.5(3) C14 C13 C12 C11 -1.5(4)