#------------------------------------------------------------------------------ #$Date: 2019-05-18 04:09:11 +0300 (Sat, 18 May 2019) $ #$Revision: 215288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123492.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_7123492 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 H25 N O4 S' _chemical_formula_sum 'C20 H25 N O4 S' _chemical_formula_weight 375.47 _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 2019-04-05 _audit_creation_method ; Olex2 1.2-ac3 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2019-04-05 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 9.7140(5) _cell_length_b 11.6951(5) _cell_length_c 16.9879(8) _cell_measurement_reflns_used 4941 _cell_measurement_temperature 150 _cell_measurement_theta_max 30.4490 _cell_measurement_theta_min 2.0960 _cell_volume 1929.93(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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 -109.00 22.00 0.50 8.00 -- -20.00 0.00-180.00 262 2 \w -14.50 17.00 0.50 8.00 -- -20.00 -72.00 -36.00 63 3 \w -110.00 -73.00 0.50 8.00 -- -20.00 0.00 108.00 74 ; _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 -0.0636512000 _diffrn_orient_matrix_UB_12 -0.0185500000 _diffrn_orient_matrix_UB_13 0.0159396000 _diffrn_orient_matrix_UB_21 -0.0159060000 _diffrn_orient_matrix_UB_22 -0.0276203000 _diffrn_orient_matrix_UB_23 -0.0360341000 _diffrn_orient_matrix_UB_31 0.0320656000 _diffrn_orient_matrix_UB_32 -0.0506892000 _diffrn_orient_matrix_UB_33 0.0138348000 _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 0.0505 _diffrn_reflns_av_unetI/netI 0.0712 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 7339 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 2.114 _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 0.192 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78443 _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 1.292 _exptl_crystal_description block _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.183 _exptl_crystal_size_mid 0.103 _exptl_crystal_size_min 0.059 _refine_diff_density_max 0.478 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.219 _refine_ls_abs_structure_details ; Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 3354 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0581 _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^)+(0.0381P)^2^+0.2541P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0907 _refine_ls_wR_factor_ref 0.1013 _reflns_Friedel_coverage 0.718 _reflns_Friedel_fraction_full 0.969 _reflns_Friedel_fraction_max 0.969 _reflns_number_gt 2959 _reflns_number_total 3354 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc03127h2.cif _cod_data_source_block sjg-dsv-8-125_mo _cod_original_cell_volume 1929.94(16) _cod_database_code 7123492 _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 0.989 _shelx_estimated_absorpt_t_min 0.966 _reflns_odcompleteness_completeness 91.13 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.13 _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, All O(H) groups 2.a Ternary CH refined with riding coordinates: C12(H12), C11(H11), C8(H8) 2.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C19(H19), C15(H15), C4(H4), C6(H6), C16(H16), C7(H7), C3(H3), C18(H18) 2.d Idealised Me refined as rotating group: C20(H20A,H20B,H20C), C1(H1A,H1B,H1C), C13(H13A,H13B,H13C) 2.e Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL sjg-dsv-8-125_mo_a.res in P2(1)2(1)2(1) sjg-dsv-8-125_mo.res created by SHELXL-2018/3 at 16:10:20 on 05-Apr-2019 REM Old TITL sjg-dsv-8-125_mo_a.res in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.135, Rweak 0.031, Alpha 0.007, Orientation as input REM Flack x = -0.097 ( 0.137 ) from Parsons' quotients REM Formula found by SHELXT: C20 N3 O2 Cl CELL 0.71073 9.714036 11.695132 16.987877 90 90 90 ZERR 4 0.000522 0.000517 0.000762 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 80 100 4 16 4 L.S. 100 PLAN 20 SIZE 0.059 0.103 0.183 TEMP -123.15 BOND $H list 4 fmap 2 acta OMIT -3 50 OMIT 1 0 1 OMIT 0 0 2 OMIT -1 1 1 OMIT 1 0 2 REM REM REM WGHT 0.038100 0.254100 FVAR 3.14968 S1 5 1.464439 1.376284 1.398355 11.00000 0.03031 0.02076 = 0.02835 0.00145 -0.00490 -0.00253 O4 4 2.141850 1.525523 1.519026 11.00000 0.02451 0.03939 = 0.03259 0.00359 -0.00251 -0.00441 O2 4 1.557269 1.312993 1.348161 11.00000 0.03019 0.02278 = 0.04313 -0.00549 -0.00516 0.00165 O1 4 1.511386 1.623575 1.243971 11.00000 0.04510 0.03181 = 0.03337 0.00983 -0.01184 -0.00431 AFIX 147 H1 2 1.498541 1.679924 1.214203 11.00000 -1.50000 AFIX 0 O3 4 1.452558 1.339293 1.478534 11.00000 0.04529 0.03481 = 0.03115 0.00843 -0.01031 -0.01119 C19 1 1.779638 1.477481 1.465507 11.00000 0.02580 0.03710 = 0.03643 0.00950 -0.00039 -0.00734 AFIX 43 H19 2 1.701580 1.436150 1.483546 11.00000 -1.20000 AFIX 0 C5 1 1.297337 1.368693 1.356835 11.00000 0.03042 0.02425 = 0.02621 -0.00657 0.00032 -0.00486 C17 1 2.016705 1.528031 1.482497 11.00000 0.02507 0.02448 = 0.02414 -0.00417 -0.00046 0.00010 C20 1 2.159891 1.445575 1.581583 11.00000 0.03422 0.05195 = 0.03190 0.00902 -0.00487 -0.00410 AFIX 137 H20A 2 2.103233 1.468510 1.626627 11.00000 -1.50000 H20B 2 2.256958 1.443970 1.597266 11.00000 -1.50000 H20C 2 2.131880 1.369312 1.563839 11.00000 -1.50000 AFIX 0 C15 1 1.885881 1.601306 1.373572 11.00000 0.03052 0.02746 = 0.03074 0.00443 0.00278 -0.00230 AFIX 43 H15 2 1.882562 1.646869 1.327314 11.00000 -1.20000 AFIX 0 N1 3 1.512267 1.507841 1.393921 11.00000 0.02452 0.02207 = 0.02709 -0.00035 0.00061 -0.00149 C14 1 1.766704 1.543438 1.398113 11.00000 0.02705 0.02087 = 0.02610 -0.00246 0.00263 0.00109 C12 1 1.635707 1.542923 1.348913 11.00000 0.02409 0.02286 = 0.02555 0.00302 0.00247 -0.00184 AFIX 13 H12 2 1.649360 1.483500 1.307312 11.00000 -1.20000 AFIX 0 C4 1 1.200707 1.296490 1.391798 11.00000 0.04164 0.02878 = 0.02863 0.00171 -0.00218 -0.00867 AFIX 43 H4 2 1.222090 1.256939 1.439088 11.00000 -1.20000 AFIX 0 C6 1 1.266439 1.427849 1.289221 11.00000 0.03056 0.03439 = 0.02433 -0.00196 -0.00074 -0.00531 AFIX 43 H6 2 1.332195 1.477642 1.266018 11.00000 -1.20000 AFIX 0 C2 1 1.039286 1.341619 1.287893 11.00000 0.02637 0.04599 = 0.03102 -0.01519 -0.00017 -0.00148 C16 1 2.007215 1.593619 1.414860 11.00000 0.03006 0.03092 = 0.03168 0.00268 0.00759 -0.00560 AFIX 43 H16 2 2.085898 1.633991 1.396682 11.00000 -1.20000 AFIX 0 C7 1 1.136675 1.413510 1.255191 11.00000 0.03385 0.04369 = 0.02328 -0.00278 0.00025 0.00044 AFIX 43 H7 2 1.114822 1.454170 1.208419 11.00000 -1.20000 AFIX 0 C3 1 1.073325 1.283371 1.356567 11.00000 0.03279 0.04012 = 0.03343 -0.00634 0.00460 -0.01150 AFIX 43 H3 2 1.007663 1.233499 1.379776 11.00000 -1.20000 AFIX 0 C11 1 1.603516 1.654884 1.305454 11.00000 0.03109 0.02559 = 0.03225 0.00740 -0.00693 -0.00401 AFIX 13 H11 2 1.690288 1.685402 1.281751 11.00000 -1.20000 AFIX 0 C18 1 1.901109 1.469093 1.507722 11.00000 0.03114 0.03926 = 0.03053 0.01293 -0.00575 -0.00468 AFIX 43 H18 2 1.905192 1.423138 1.553776 11.00000 -1.20000 AFIX 0 C1 1 0.898920 1.326942 1.250787 11.00000 0.03177 0.06837 = 0.04230 -0.01782 -0.00318 -0.00352 AFIX 137 H1A 2 0.895654 1.254074 1.222363 11.00000 -1.50000 H1B 2 0.881850 1.389885 1.213978 11.00000 -1.50000 H1C 2 0.828274 1.327352 1.291969 11.00000 -1.50000 AFIX 0 C10 1 1.542183 1.744929 1.359388 11.00000 0.04177 0.02096 = 0.04555 0.00157 -0.00602 -0.00095 AFIX 23 H10A 2 1.521707 1.814880 1.328729 11.00000 -1.20000 H10B 2 1.609598 1.765049 1.400840 11.00000 -1.20000 AFIX 0 C8 1 1.434791 1.590415 1.444121 11.00000 0.02633 0.02782 = 0.03301 -0.00598 0.00318 -0.00077 AFIX 13 H8 2 1.342454 1.555745 1.454494 11.00000 -1.20000 AFIX 0 C9 1 1.409927 1.700544 1.397559 11.00000 0.03283 0.02597 = 0.04341 -0.00391 0.00222 -0.00027 AFIX 23 H9A 2 1.340458 1.685923 1.356124 11.00000 -1.20000 H9B 2 1.372655 1.759793 1.433311 11.00000 -1.20000 AFIX 0 C13 1 1.501602 1.611788 1.524143 11.00000 0.05015 0.03838 = 0.03408 -0.01149 0.00060 -0.00371 AFIX 137 H13A 2 1.587887 1.653898 1.516856 11.00000 -1.50000 H13B 2 1.520792 1.538440 1.549788 11.00000 -1.50000 H13C 2 1.439005 1.656743 1.557141 11.00000 -1.50000 AFIX 0 HKLF 4 REM sjg-dsv-8-125_mo_a.res in P2(1)2(1)2(1) REM wR2 = 0.1013, GooF = S = 1.069, Restrained GooF = 1.069 for all data REM R1 = 0.0438 for 2959 Fo > 4sig(Fo) and 0.0581 for all 3354 data REM 239 parameters refined using 0 restraints END WGHT 0.0384 0.2533 REM Highest difference peak 0.478, deepest hole -0.642, 1-sigma level 0.219 Q1 1 1.2627 1.7025 1.2805 11.00000 0.05 0.48 Q2 1 1.2546 1.7995 1.3577 11.00000 0.05 0.47 Q3 1 1.2702 1.6915 1.3425 11.00000 0.05 0.45 Q4 1 0.7712 1.3897 1.2536 11.00000 0.05 0.44 Q5 1 0.7292 1.4032 1.1830 11.00000 0.05 0.43 Q6 1 0.7462 1.3672 1.2329 11.00000 0.05 0.43 Q7 1 0.7203 1.2817 1.2576 11.00000 0.05 0.43 Q8 1 1.7850 1.4868 1.4152 11.00000 0.05 0.41 Q9 1 1.7467 1.3855 1.4509 11.00000 0.05 0.41 Q10 1 0.7427 1.4220 1.1237 11.00000 0.05 0.40 Q11 1 1.2509 1.7406 1.5179 11.00000 0.05 0.40 Q12 1 1.2784 1.7811 1.3040 11.00000 0.05 0.40 Q13 1 1.2558 1.5817 1.3604 11.00000 0.05 0.40 Q14 1 2.1994 1.6945 1.4208 11.00000 0.05 0.40 Q15 1 0.7642 1.2598 1.3185 11.00000 0.05 0.40 Q16 1 2.2647 1.3806 1.5869 11.00000 0.05 0.39 Q17 1 2.2185 1.6900 1.4485 11.00000 0.05 0.39 Q18 1 1.2422 1.5356 1.2358 11.00000 0.05 0.39 Q19 1 1.7265 1.4324 1.2984 11.00000 0.05 0.39 Q20 1 1.7797 1.6650 1.4179 11.00000 0.05 0.39 ; _shelx_res_checksum 76769 _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 1.406 _oxdiff_exptl_absorpt_empirical_full_min 0.777 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 1.46444(10) 1.37628(7) 1.39836(6) 0.0265(2) Uani 1 1 d . O4 O 2.1418(3) 1.5255(2) 1.51903(16) 0.0322(7) Uani 1 1 d . O2 O 1.5573(3) 1.31299(19) 1.34816(16) 0.0320(7) Uani 1 1 d . O1 O 1.5114(3) 1.6236(2) 1.24397(16) 0.0368(7) Uani 1 1 d . H1 H 1.498541 1.679924 1.214203 0.055 Uiso 1 1 calc GR O3 O 1.4526(3) 1.3393(2) 1.47853(15) 0.0371(7) Uani 1 1 d . C19 C 1.7796(4) 1.4775(3) 1.4655(2) 0.0331(10) Uani 1 1 d . H19 H 1.701580 1.436150 1.483546 0.040 Uiso 1 1 calc R C5 C 1.2973(4) 1.3687(3) 1.3568(2) 0.0270(8) Uani 1 1 d . C17 C 2.0167(4) 1.5280(3) 1.4825(2) 0.0246(8) Uani 1 1 d . C20 C 2.1599(4) 1.4456(4) 1.5816(2) 0.0394(11) Uani 1 1 d . H20A H 2.103233 1.468510 1.626627 0.059 Uiso 1 1 calc GR H20B H 2.256958 1.443970 1.597266 0.059 Uiso 1 1 calc GR H20C H 2.131880 1.369312 1.563839 0.059 Uiso 1 1 calc GR C15 C 1.8859(4) 1.6013(3) 1.3736(2) 0.0296(9) Uani 1 1 d . H15 H 1.882562 1.646869 1.327314 0.035 Uiso 1 1 calc R N1 N 1.5123(3) 1.5078(2) 1.39392(18) 0.0246(7) Uani 1 1 d . C14 C 1.7667(4) 1.5434(3) 1.3981(2) 0.0247(8) Uani 1 1 d . C12 C 1.6357(4) 1.5429(3) 1.3489(2) 0.0242(8) Uani 1 1 d . H12 H 1.649360 1.483500 1.307312 0.029 Uiso 1 1 calc R C4 C 1.2007(4) 1.2965(3) 1.3918(2) 0.0330(10) Uani 1 1 d . H4 H 1.222090 1.256939 1.439088 0.040 Uiso 1 1 calc R C6 C 1.2664(4) 1.4278(3) 1.2892(2) 0.0298(9) Uani 1 1 d . H6 H 1.332195 1.477642 1.266018 0.036 Uiso 1 1 calc R C2 C 1.0393(4) 1.3416(3) 1.2879(2) 0.0345(10) Uani 1 1 d . C16 C 2.0072(4) 1.5936(3) 1.4149(2) 0.0309(9) Uani 1 1 d . H16 H 2.085898 1.633991 1.396682 0.037 Uiso 1 1 calc R C7 C 1.1367(4) 1.4135(3) 1.2552(2) 0.0336(10) Uani 1 1 d . H7 H 1.114822 1.454170 1.208419 0.040 Uiso 1 1 calc R C3 C 1.0733(4) 1.2834(3) 1.3566(2) 0.0354(10) Uani 1 1 d . H3 H 1.007663 1.233499 1.379776 0.043 Uiso 1 1 calc R C11 C 1.6035(4) 1.6549(3) 1.3055(2) 0.0296(9) Uani 1 1 d . H11 H 1.690288 1.685402 1.281751 0.036 Uiso 1 1 calc R C18 C 1.9011(4) 1.4691(3) 1.5077(2) 0.0336(10) Uani 1 1 d . H18 H 1.905192 1.423138 1.553776 0.040 Uiso 1 1 calc R C1 C 0.8989(4) 1.3269(4) 1.2508(3) 0.0475(12) Uani 1 1 d . H1A H 0.895654 1.254074 1.222363 0.071 Uiso 1 1 calc GR H1B H 0.881850 1.389885 1.213978 0.071 Uiso 1 1 calc GR H1C H 0.828274 1.327352 1.291969 0.071 Uiso 1 1 calc GR C10 C 1.5422(5) 1.7449(3) 1.3594(2) 0.0361(10) Uani 1 1 d . H10A H 1.521707 1.814880 1.328729 0.043 Uiso 1 1 calc R H10B H 1.609598 1.765049 1.400840 0.043 Uiso 1 1 calc R C8 C 1.4348(4) 1.5904(3) 1.4441(2) 0.0291(9) Uani 1 1 d . H8 H 1.342454 1.555745 1.454494 0.035 Uiso 1 1 calc R C9 C 1.4099(4) 1.7005(3) 1.3976(3) 0.0341(10) Uani 1 1 d . H9A H 1.340458 1.685923 1.356124 0.041 Uiso 1 1 calc R H9B H 1.372655 1.759793 1.433311 0.041 Uiso 1 1 calc R C13 C 1.5016(5) 1.6118(4) 1.5241(2) 0.0409(11) Uani 1 1 d . H13A H 1.587887 1.653898 1.516856 0.061 Uiso 1 1 calc GR H13B H 1.520792 1.538440 1.549788 0.061 Uiso 1 1 calc GR H13C H 1.439005 1.656743 1.557141 0.061 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 0.0303(5) 0.0208(4) 0.0284(5) 0.0014(4) -0.0049(5) -0.0025(4) O4 0.0245(15) 0.0394(15) 0.0326(15) 0.0036(13) -0.0025(14) -0.0044(12) O2 0.0302(15) 0.0228(13) 0.0431(15) -0.0055(12) -0.0052(14) 0.0016(12) O1 0.0451(17) 0.0318(14) 0.0334(14) 0.0098(12) -0.0118(14) -0.0043(14) O3 0.0453(18) 0.0348(14) 0.0311(14) 0.0084(12) -0.0103(15) -0.0112(13) C19 0.026(2) 0.037(2) 0.036(2) 0.0095(19) 0.000(2) -0.0073(18) C5 0.030(2) 0.0243(18) 0.0262(19) -0.0066(17) 0.0003(18) -0.0049(18) C17 0.025(2) 0.0245(17) 0.0241(18) -0.0042(15) -0.0005(18) 0.0001(16) C20 0.034(3) 0.052(3) 0.032(2) 0.009(2) -0.005(2) -0.004(2) C15 0.031(2) 0.0275(19) 0.031(2) 0.0044(17) 0.0028(19) -0.0023(17) N1 0.0245(18) 0.0221(14) 0.0271(15) -0.0004(13) 0.0006(16) -0.0015(12) C14 0.027(2) 0.0209(18) 0.0261(18) -0.0025(18) 0.0026(19) 0.0011(15) C12 0.024(2) 0.0229(18) 0.0256(19) 0.0030(16) 0.0025(18) -0.0018(16) C4 0.042(2) 0.0288(19) 0.029(2) 0.0017(18) -0.002(2) -0.0087(18) C6 0.031(2) 0.034(2) 0.0243(19) -0.0020(18) -0.0007(19) -0.0053(18) C2 0.026(2) 0.046(2) 0.031(2) -0.0152(18) 0.000(2) -0.0015(19) C16 0.030(2) 0.031(2) 0.032(2) 0.0027(17) 0.0076(18) -0.0056(17) C7 0.034(2) 0.044(2) 0.023(2) -0.0028(19) 0.000(2) 0.000(2) C3 0.033(3) 0.040(2) 0.033(2) -0.006(2) 0.005(2) -0.0115(19) C11 0.031(2) 0.0256(19) 0.032(2) 0.0074(17) -0.0069(19) -0.0040(16) C18 0.031(2) 0.039(2) 0.031(2) 0.013(2) -0.006(2) -0.0047(18) C1 0.032(3) 0.068(3) 0.042(3) -0.018(2) -0.003(2) -0.004(2) C10 0.042(3) 0.0210(18) 0.046(2) 0.0016(18) -0.006(2) -0.0009(19) C8 0.026(2) 0.028(2) 0.033(2) -0.0060(17) 0.0032(18) -0.0008(17) C9 0.033(2) 0.0260(19) 0.043(2) -0.004(2) 0.002(2) -0.0003(17) C13 0.050(3) 0.038(2) 0.034(2) -0.0115(19) 0.001(2) -0.004(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 C5 108.12(16) O2 S1 N1 106.38(16) O3 S1 O2 117.15(16) O3 S1 C5 106.81(18) O3 S1 N1 110.87(16) N1 S1 C5 107.08(17) C17 O4 C20 117.5(3) C11 O1 H1 109.5 C14 C19 H19 118.5 C18 C19 H19 118.5 C18 C19 C14 123.0(4) C4 C5 S1 118.5(3) C6 C5 S1 120.5(3) C6 C5 C4 120.9(4) O4 C17 C16 116.6(3) O4 C17 C18 124.8(3) C16 C17 C18 118.6(4) O4 C20 H20A 109.5 O4 C20 H20B 109.5 O4 C20 H20C 109.5 H20A C20 H20B 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C14 C15 H15 119.2 C16 C15 H15 119.2 C16 C15 C14 121.6(3) C12 N1 S1 121.5(2) C12 N1 C8 121.6(3) C8 N1 S1 116.5(2) C19 C14 C15 116.0(4) C19 C14 C12 121.8(3) C15 C14 C12 121.9(3) N1 C12 C14 113.2(3) N1 C12 H12 106.3 N1 C12 C11 108.7(3) C14 C12 H12 106.3 C14 C12 C11 115.5(3) C11 C12 H12 106.3 C5 C4 H4 120.5 C3 C4 C5 119.0(4) C3 C4 H4 120.5 C5 C6 H6 120.6 C5 C6 C7 118.9(4) C7 C6 H6 120.6 C7 C2 C3 118.2(4) C7 C2 C1 121.2(4) C3 C2 C1 120.6(4) C17 C16 H16 119.4 C15 C16 C17 121.1(4) C15 C16 H16 119.4 C6 C7 H7 119.2 C2 C7 C6 121.6(4) C2 C7 H7 119.2 C4 C3 C2 121.4(4) C4 C3 H3 119.3 C2 C3 H3 119.3 O1 C11 C12 105.2(3) O1 C11 H11 109.0 O1 C11 C10 112.0(3) C12 C11 H11 109.0 C10 C11 C12 112.4(3) C10 C11 H11 109.0 C19 C18 C17 119.7(3) C19 C18 H18 120.2 C17 C18 H18 120.2 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 C11 C10 H10A 109.6 C11 C10 H10B 109.6 C11 C10 C9 110.5(3) H10A C10 H10B 108.1 C9 C10 H10A 109.6 C9 C10 H10B 109.6 N1 C8 H8 106.9 N1 C8 C9 109.2(3) N1 C8 C13 113.6(3) C9 C8 H8 106.9 C13 C8 H8 106.9 C13 C8 C9 112.9(3) C10 C9 C8 111.8(3) C10 C9 H9A 109.2 C10 C9 H9B 109.2 C8 C9 H9A 109.2 C8 C9 H9B 109.2 H9A C9 H9B 107.9 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 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O2 1.445(3) S1 O3 1.434(3) S1 C5 1.772(4) S1 N1 1.609(3) O4 C17 1.365(5) O4 C20 1.426(4) O1 H1 0.8400 O1 C11 1.423(4) C19 H19 0.9500 C19 C14 1.386(5) C19 C18 1.384(5) C5 C4 1.395(5) C5 C6 1.374(5) C17 C16 1.385(5) C17 C18 1.386(5) C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 C15 H15 0.9500 C15 C14 1.404(5) C15 C16 1.374(5) N1 C12 1.480(5) N1 C8 1.492(5) C14 C12 1.522(5) C12 H12 1.0000 C12 C11 1.535(5) C4 H4 0.9500 C4 C3 1.383(5) C6 H6 0.9500 C6 C7 1.397(5) C2 C7 1.382(6) C2 C3 1.391(5) C2 C1 1.512(6) C16 H16 0.9500 C7 H7 0.9500 C3 H3 0.9500 C11 H11 1.0000 C11 C10 1.518(5) C18 H18 0.9500 C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800 C10 H10A 0.9900 C10 H10B 0.9900 C10 C9 1.530(5) C8 H8 1.0000 C8 C9 1.531(5) C8 C13 1.527(5) C9 H9A 0.9900 C9 H9B 0.9900 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800