#------------------------------------------------------------------------------ #$Date: 2021-11-03 00:58:25 +0200 (Wed, 03 Nov 2021) $ #$Revision: 270214 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129185.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_7129185 loop_ _publ_author_name 'Zhou, Su' 'Xie, Xiongda' 'Xu, Xinxin' 'Dong, Shanliang' 'Hu, Wenhao' 'Xu, Xinfang' _publ_section_title ; An asymmetric oxidative cyclization/Mannich-type addition cascade reaction for direct access to chiral pyrrolidin-3-ones ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC04830A _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C21 H25 Cl N2 O3 S' _chemical_formula_sum 'C21 H25 Cl N2 O3 S' _chemical_formula_weight 420.94 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-04-09 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-04-11 deposited with the CCDC. 2021-10-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.671(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.1972(2) _cell_length_b 13.8507(2) _cell_length_c 11.1349(2) _cell_measurement_reflns_used 6502 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 77.0250 _cell_measurement_theta_min 4.1780 _cell_volume 1051.58(4) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.959 _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 -69.00 -27.00 0.50 2.50 -- -100.00 61.00 60.00 84 2 \w -24.00 29.00 0.50 0.50 -- -46.62 19.00 0.00 106 3 \w -24.00 29.00 0.50 0.50 -- -46.62 19.00 -90.00 106 4 \w -69.00 -27.00 0.50 2.50 -- -100.00 61.00 150.00 84 5 \w -108.00 -27.00 0.50 2.50 -- -100.00 111.00 66.00 162 6 \w -120.00 -32.00 0.50 0.50 -- -46.62 -39.00 53.00 176 7 \w -119.00 -74.00 0.50 0.50 -- -46.62-125.00 -60.00 90 8 \w -119.00 -74.00 0.50 0.50 -- -46.62-125.00-180.00 90 9 \w -173.00 -80.00 0.50 2.50 -- -100.00 -86.00-135.00 186 10 \w -173.00 -85.00 0.50 2.50 -- -100.00 -39.00 53.00 176 11 \w -119.00 -74.00 0.50 0.50 -- -46.62-125.00 90.00 90 12 \w -175.00 -82.00 0.50 2.50 -- -100.00 -15.00 -30.00 186 13 \w 34.00 108.00 0.50 2.50 -- 107.00-111.00 -27.00 148 14 \w 34.00 106.00 0.50 2.50 -- 107.00 -94.00 90.00 144 15 \w 34.00 73.00 0.50 2.50 -- 107.00 -61.00 90.00 78 16 \w 34.00 112.00 0.50 2.50 -- 107.00-125.00 30.00 156 17 \w 34.00 73.00 0.50 2.50 -- 107.00 -61.00 -90.00 78 18 \w 34.00 73.00 0.50 2.50 -- 107.00 -61.00-120.00 78 19 \w 34.00 73.00 0.50 2.50 -- 107.00 -61.00 -60.00 78 20 \w 34.00 106.00 0.50 2.50 -- 107.00 -94.00-120.00 144 21 \w 34.00 102.00 0.50 2.50 -- 107.00-125.00-150.00 136 22 \w 92.00 178.00 0.50 2.50 -- 107.00 30.00 -60.00 172 23 \w 80.00 105.00 0.50 2.50 -- 107.00 125.00 -90.00 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.2121478000 _diffrn_orient_matrix_UB_12 0.0365276000 _diffrn_orient_matrix_UB_13 0.0295072000 _diffrn_orient_matrix_UB_21 0.0061971000 _diffrn_orient_matrix_UB_22 -0.0411020000 _diffrn_orient_matrix_UB_23 -0.1272320000 _diffrn_orient_matrix_UB_31 -0.0775702000 _diffrn_orient_matrix_UB_32 0.0966659000 _diffrn_orient_matrix_UB_33 -0.0652340000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_unetI/netI 0.0479 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.959 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10375 _diffrn_reflns_point_group_measured_fraction_full 0.846 _diffrn_reflns_point_group_measured_fraction_max 0.801 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.172 _diffrn_reflns_theta_min 4.191 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.733 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) 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 1.329 _exptl_crystal_description plate _exptl_crystal_F_000 444 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.199 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.007(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 3557 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0318 _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^)+(0.0296P)^2^+0.2377P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.0786 _reflns_Friedel_coverage 0.601 _reflns_Friedel_fraction_full 0.686 _reflns_Friedel_fraction_max 0.628 _reflns_number_gt 3323 _reflns_number_total 3557 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc04830a2.cif _cod_data_source_block zhous_210409 _cod_database_code 7129185 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula CHONCl _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 0.875 _shelx_estimated_absorpt_t_min 0.772 _reflns_odcompleteness_completeness 99.03 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 71.98 _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.a Ternary CH refined with riding coordinates: C00A(H00A), C00P(H00T) 2.b Secondary CH2 refined with riding coordinates: C00K(H00K,H00L), C00M(H00N,H00O) 2.c Aromatic/amide H refined with riding coordinates: N006(H006), C008(H008), C00B(H00B), C00D(H00D), C00I(H00I), C00L(H00M), C00O(H00S), C00Q(H00U), C00R(H00V), C00S(H00W) 2.d Idealised Me refined as rotating group: C00G(H00C,H00E,H00F), C00J(H00G,H00H,H00J), C00N(H00P,H00Q,H00R) ; _shelx_res_file ; TITL zhous_210409_a.res in P2(1) zhous_210409.res created by SHELXL-2018/3 at 15:30:34 on 09-Apr-2021 REM Old TITL zhous_210409_a.res in P2(1) REM SHELXT solution in P2(1): R1 0.071, Rweak 0.028, Alpha 0.001 REM 0.339 for 9 systematic absences, Orientation as input REM Flack x = 0.066 ( 0.010 ) from 1174 Parsons' quotients REM Formula found by SHELXT: C21 N2 O3 Cl2 CELL 1.54184 7.1972 13.8507 11.1349 90 108.671 90 ZERR 2 0.0002 0.0002 0.0002 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Cl N O S UNIT 42 50 2 4 6 2 L.S. 4 PLAN 4 SIZE 0.05 0.1 0.1 CONF BOND $h list 4 fmap 2 htab MORE -1 ACTA OMIT -4 -10 11 OMIT -4 -8 12 REM REM REM WGHT 0.029600 0.237700 FVAR 0.89679 S01 6 0.337134 0.348560 0.666038 11.00000 0.01641 0.01428 = 0.01974 -0.00059 0.00761 0.00070 CL02 3 0.933546 0.523550 1.070894 11.00000 0.03603 0.03929 = 0.01895 0.00264 0.00876 0.00100 O003 5 0.545376 0.353722 0.728644 11.00000 0.01553 0.02214 = 0.02750 0.00609 0.00908 0.00305 O004 5 0.257312 0.266530 0.587003 11.00000 0.02701 0.01624 = 0.02556 -0.00327 0.01284 -0.00061 O005 5 0.276023 0.684963 0.487504 11.00000 0.02860 0.01942 = 0.04229 0.00655 0.00306 0.00026 N006 4 0.701605 0.609747 0.598859 11.00000 0.02112 0.01850 = 0.01947 0.00458 0.00422 -0.00401 AFIX 43 H006 2 0.701323 0.649139 0.539100 11.00000 -1.20000 AFIX 0 N007 4 0.270973 0.443652 0.577538 11.00000 0.01661 0.01785 = 0.01792 -0.00008 0.00528 -0.00402 C008 1 0.576308 0.390341 0.416058 11.00000 0.01831 0.02012 = 0.02130 0.00258 0.00429 0.00121 AFIX 43 H008 2 0.603019 0.348770 0.485102 11.00000 -1.20000 AFIX 0 C009 1 0.556425 0.488573 0.433799 11.00000 0.01599 0.02183 = 0.02029 0.00120 0.00912 -0.00232 C00A 1 0.582672 0.523419 0.566931 11.00000 0.01641 0.01829 = 0.01803 0.00047 0.00446 -0.00071 AFIX 13 H00A 2 0.656267 0.472752 0.623907 11.00000 -1.20000 AFIX 0 C00B 1 0.513524 0.550046 0.328997 11.00000 0.02136 0.02450 = 0.02190 0.00182 0.00404 -0.00242 AFIX 43 H00B 2 0.496525 0.615788 0.338904 11.00000 -1.20000 AFIX 0 C00C 1 0.937515 0.598312 0.945607 11.00000 0.02369 0.02409 = 0.02138 -0.00424 0.00896 0.00478 C00D 1 0.815011 0.574029 0.825733 11.00000 0.01829 0.01885 = 0.02082 -0.00199 0.00835 0.00008 AFIX 43 H00D 2 0.733379 0.520419 0.814341 11.00000 -1.20000 AFIX 0 C00E 1 0.815249 0.631422 0.721032 11.00000 0.01730 0.01758 = 0.02187 -0.00101 0.00723 0.00211 C00F 1 0.240517 0.601474 0.501621 11.00000 0.02353 0.01787 = 0.02266 -0.00070 0.00938 0.00159 C00G 1 0.280832 0.449923 0.860504 11.00000 0.02380 0.02204 = 0.01867 -0.00170 0.00801 0.00107 AFIX 137 H00C 2 0.421088 0.455986 0.889565 11.00000 -1.50000 H00E 2 0.233512 0.450751 0.931906 11.00000 -1.50000 H00F 2 0.224322 0.502799 0.805111 11.00000 -1.50000 AFIX 0 C00H 1 0.222693 0.354528 0.788565 11.00000 0.01743 0.02021 = 0.02014 0.00193 0.00665 0.00148 C00I 1 0.941269 0.711213 0.743780 11.00000 0.02498 0.02055 = 0.02625 0.00461 0.00718 -0.00185 AFIX 43 H00I 2 0.944450 0.749885 0.676189 11.00000 -1.20000 AFIX 0 C00J 1 0.300693 0.267728 0.874900 11.00000 0.02760 0.02314 = 0.02720 0.00163 0.01388 -0.00233 AFIX 137 H00G 2 0.267959 0.209323 0.826254 11.00000 -1.50000 H00H 2 0.242479 0.266684 0.941345 11.00000 -1.50000 H00J 2 0.440599 0.272695 0.911294 11.00000 -1.50000 AFIX 0 C00K 1 0.055387 0.548320 0.432846 11.00000 0.02093 0.02432 = 0.01957 0.00090 0.00458 0.00331 AFIX 23 H00K 2 0.012984 0.563498 0.343090 11.00000 -1.20000 H00L 2 -0.048772 0.565037 0.466866 11.00000 -1.20000 AFIX 0 C00L 1 0.556876 0.353178 0.296564 11.00000 0.02845 0.02300 = 0.02468 0.00047 0.00750 0.00470 AFIX 43 H00M 2 0.568813 0.287163 0.285644 11.00000 -1.20000 AFIX 0 C00M 1 0.108564 0.441882 0.454723 11.00000 0.01951 0.02131 = 0.01919 -0.00199 0.00419 -0.00111 AFIX 23 H00N 2 -0.001596 0.404185 0.460905 11.00000 -1.20000 H00O 2 0.152154 0.415847 0.387404 11.00000 -1.20000 AFIX 0 C00N 1 0.000612 0.348917 0.727771 11.00000 0.01671 0.03082 = 0.02726 -0.00331 0.01019 -0.00242 AFIX 137 H00P 2 -0.044443 0.403921 0.673831 11.00000 -1.50000 H00Q 2 -0.060450 0.348409 0.792819 11.00000 -1.50000 H00R 2 -0.033054 0.290891 0.678399 11.00000 -1.50000 AFIX 0 C00O 1 0.496252 0.512982 0.209981 11.00000 0.02832 0.03190 = 0.01840 0.00078 0.00487 -0.00181 AFIX 43 H00S 2 0.468771 0.554235 0.140581 11.00000 -1.20000 AFIX 0 C00P 1 0.383627 0.533810 0.594461 11.00000 0.01736 0.01636 = 0.01873 -0.00066 0.00530 -0.00095 AFIX 13 H00T 2 0.408688 0.557587 0.681107 11.00000 -1.20000 AFIX 0 C00Q 1 0.519580 0.415276 0.193862 11.00000 0.03097 0.03480 = 0.01808 -0.00275 0.00649 0.00099 AFIX 43 H00U 2 0.510266 0.391202 0.114175 11.00000 -1.20000 AFIX 0 C00R 1 1.060750 0.733539 0.864506 11.00000 0.02911 0.02399 = 0.03408 -0.00449 0.00419 -0.00713 AFIX 43 H00V 2 1.142256 0.787262 0.877004 11.00000 -1.20000 AFIX 0 C00S 1 1.061336 0.676792 0.968281 11.00000 0.02270 0.02909 = 0.02332 -0.00699 0.00156 -0.00057 AFIX 43 H00W 2 1.142373 0.691469 1.049702 11.00000 -1.20000 AFIX 0 HKLF 4 REM zhous_210409_a.res in P2(1) REM wR2 = 0.0786, GooF = S = 1.068, Restrained GooF = 1.068 for all data REM R1 = 0.0318 for 3323 Fo > 4sig(Fo) and 0.0349 for all 3557 data REM 256 parameters refined using 1 restraints END WGHT 0.0297 0.2380 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y+1/2, -z+1 HTAB N006 O004_$1 HTAB C00A O003 EQIV $2 x-1, y, z-1 HTAB C00K Cl02_$2 EQIV $3 -x, y-1/2, -z+1 HTAB C00N O005_$3 REM Highest difference peak 0.199, deepest hole -0.353, 1-sigma level 0.049 Q1 1 1.2049 0.6970 1.2178 11.00000 0.05 0.20 Q2 1 0.4853 0.5310 0.5893 11.00000 0.05 0.18 Q3 1 0.5648 0.4376 0.4197 11.00000 0.05 0.17 Q4 1 0.3208 0.2197 0.7755 11.00000 0.05 0.17 ; _shelx_res_checksum 57322 _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 ; _oxdiff_exptl_absorpt_empirical_full_max 2.113 _oxdiff_exptl_absorpt_empirical_full_min 0.471 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S01 S 0.33713(9) 0.34856(5) 0.66604(6) 0.01638(16) Uani 1 1 d . . . . . Cl02 Cl 0.93355(13) 0.52355(6) 1.07089(7) 0.0314(2) Uani 1 1 d . . . . . O003 O 0.5454(3) 0.35372(18) 0.7286(2) 0.0212(4) Uani 1 1 d . . . . . O004 O 0.2573(3) 0.26653(16) 0.5870(2) 0.0219(5) Uani 1 1 d . . . . . O005 O 0.2760(4) 0.68496(17) 0.4875(3) 0.0321(6) Uani 1 1 d . . . . . N006 N 0.7016(4) 0.60975(19) 0.5989(2) 0.0202(5) Uani 1 1 d . . . . . H006 H 0.701323 0.649139 0.539100 0.024 Uiso 1 1 calc R U . . . N007 N 0.2710(4) 0.44365(19) 0.5775(2) 0.0175(5) Uani 1 1 d . . . . . C008 C 0.5763(4) 0.3903(2) 0.4161(3) 0.0204(6) Uani 1 1 d . . . . . H008 H 0.603019 0.348770 0.485102 0.024 Uiso 1 1 calc R U . . . C009 C 0.5564(4) 0.4886(2) 0.4338(3) 0.0186(6) Uani 1 1 d . . . . . C00A C 0.5827(4) 0.5234(2) 0.5669(3) 0.0178(6) Uani 1 1 d . . . . . H00A H 0.656267 0.472752 0.623907 0.021 Uiso 1 1 calc R U . . . C00B C 0.5135(5) 0.5500(2) 0.3290(3) 0.0233(7) Uani 1 1 d . . . . . H00B H 0.496525 0.615788 0.338904 0.028 Uiso 1 1 calc R U . . . C00C C 0.9375(5) 0.5983(2) 0.9456(3) 0.0226(6) Uani 1 1 d . . . . . C00D C 0.8150(4) 0.5740(2) 0.8257(3) 0.0188(6) Uani 1 1 d . . . . . H00D H 0.733379 0.520419 0.814341 0.023 Uiso 1 1 calc R U . . . C00E C 0.8152(4) 0.6314(2) 0.7210(3) 0.0187(6) Uani 1 1 d . . . . . C00F C 0.2405(4) 0.6015(2) 0.5016(3) 0.0209(6) Uani 1 1 d . . . . . C00G C 0.2808(5) 0.4499(2) 0.8605(3) 0.0212(6) Uani 1 1 d . . . . . H00C H 0.421088 0.455986 0.889565 0.032 Uiso 1 1 calc R U . . . H00E H 0.233512 0.450751 0.931906 0.032 Uiso 1 1 calc R U . . . H00F H 0.224322 0.502799 0.805111 0.032 Uiso 1 1 calc R U . . . C00H C 0.2227(4) 0.3545(3) 0.7886(3) 0.0191(6) Uani 1 1 d . . . . . C00I C 0.9413(5) 0.7112(2) 0.7438(3) 0.0242(7) Uani 1 1 d . . . . . H00I H 0.944450 0.749885 0.676189 0.029 Uiso 1 1 calc R U . . . C00J C 0.3007(5) 0.2677(3) 0.8749(3) 0.0248(7) Uani 1 1 d . . . . . H00G H 0.267959 0.209323 0.826254 0.037 Uiso 1 1 calc R U . . . H00H H 0.242479 0.266684 0.941345 0.037 Uiso 1 1 calc R U . . . H00J H 0.440599 0.272695 0.911294 0.037 Uiso 1 1 calc R U . . . C00K C 0.0554(4) 0.5483(2) 0.4328(3) 0.0221(7) Uani 1 1 d . . . . . H00K H 0.012984 0.563498 0.343090 0.026 Uiso 1 1 calc R U . . . H00L H -0.048772 0.565037 0.466866 0.026 Uiso 1 1 calc R U . . . C00L C 0.5569(4) 0.3532(3) 0.2966(3) 0.0256(6) Uani 1 1 d . . . . . H00M H 0.568813 0.287163 0.285644 0.031 Uiso 1 1 calc R U . . . C00M C 0.1086(4) 0.4419(2) 0.4547(3) 0.0205(6) Uani 1 1 d . . . . . H00N H -0.001596 0.404185 0.460905 0.025 Uiso 1 1 calc R U . . . H00O H 0.152154 0.415847 0.387404 0.025 Uiso 1 1 calc R U . . . C00N C 0.0006(4) 0.3489(3) 0.7278(3) 0.0242(6) Uani 1 1 d . . . . . H00P H -0.044443 0.403921 0.673831 0.036 Uiso 1 1 calc R U . . . H00Q H -0.060450 0.348409 0.792819 0.036 Uiso 1 1 calc R U . . . H00R H -0.033054 0.290891 0.678399 0.036 Uiso 1 1 calc R U . . . C00O C 0.4963(5) 0.5130(3) 0.2100(3) 0.0268(7) Uani 1 1 d . . . . . H00S H 0.468771 0.554235 0.140581 0.032 Uiso 1 1 calc R U . . . C00P C 0.3836(4) 0.5338(2) 0.5945(3) 0.0176(6) Uani 1 1 d . . . . . H00T H 0.408688 0.557587 0.681107 0.021 Uiso 1 1 calc R U . . . C00Q C 0.5196(5) 0.4153(3) 0.1939(3) 0.0283(7) Uani 1 1 d . . . . . H00U H 0.510266 0.391202 0.114175 0.034 Uiso 1 1 calc R U . . . C00R C 1.0608(5) 0.7335(3) 0.8645(3) 0.0305(8) Uani 1 1 d . . . . . H00V H 1.142256 0.787262 0.877004 0.037 Uiso 1 1 calc R U . . . C00S C 1.0613(5) 0.6768(3) 0.9683(3) 0.0264(7) Uani 1 1 d . . . . . H00W H 1.142373 0.691469 1.049702 0.032 Uiso 1 1 calc R U . . . 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 S01 0.0164(3) 0.0143(3) 0.0197(3) -0.0006(3) 0.0076(2) 0.0007(3) Cl02 0.0360(4) 0.0393(5) 0.0190(3) 0.0026(3) 0.0088(3) 0.0010(4) O003 0.0155(9) 0.0221(10) 0.0275(11) 0.0061(10) 0.0091(8) 0.0030(9) O004 0.0270(12) 0.0162(11) 0.0256(11) -0.0033(9) 0.0128(9) -0.0006(9) O005 0.0286(12) 0.0194(12) 0.0423(14) 0.0065(10) 0.0031(10) 0.0003(9) N006 0.0211(12) 0.0185(13) 0.0195(12) 0.0046(10) 0.0042(10) -0.0040(10) N007 0.0166(11) 0.0179(13) 0.0179(12) -0.0001(10) 0.0053(10) -0.0040(10) C008 0.0183(14) 0.0201(14) 0.0213(15) 0.0026(11) 0.0043(11) 0.0012(11) C009 0.0160(13) 0.0218(15) 0.0203(15) 0.0012(12) 0.0091(11) -0.0023(11) C00A 0.0164(13) 0.0183(14) 0.0180(13) 0.0005(12) 0.0045(10) -0.0007(11) C00B 0.0214(15) 0.0245(17) 0.0219(15) 0.0018(12) 0.0040(12) -0.0024(12) C00C 0.0237(15) 0.0241(16) 0.0214(15) -0.0042(12) 0.0090(12) 0.0048(12) C00D 0.0183(13) 0.0188(15) 0.0208(14) -0.0020(11) 0.0084(11) 0.0001(11) C00E 0.0173(13) 0.0176(15) 0.0219(15) -0.0010(12) 0.0072(11) 0.0021(11) C00F 0.0235(15) 0.0179(15) 0.0227(15) -0.0007(12) 0.0094(12) 0.0016(11) C00G 0.0238(15) 0.0220(16) 0.0187(14) -0.0017(12) 0.0080(12) 0.0011(12) C00H 0.0174(12) 0.0202(14) 0.0201(14) 0.0019(13) 0.0066(10) 0.0015(12) C00I 0.0250(15) 0.0205(16) 0.0262(17) 0.0046(13) 0.0072(13) -0.0018(13) C00J 0.0276(17) 0.0231(17) 0.0272(16) 0.0016(13) 0.0139(13) -0.0023(13) C00K 0.0209(14) 0.0243(17) 0.0196(14) 0.0009(12) 0.0046(12) 0.0033(12) C00L 0.0285(14) 0.0230(15) 0.0247(15) 0.0005(14) 0.0075(12) 0.0047(14) C00M 0.0195(14) 0.0213(15) 0.0192(14) -0.0020(12) 0.0042(12) -0.0011(11) C00N 0.0167(13) 0.0308(16) 0.0273(15) -0.0033(16) 0.0102(11) -0.0024(15) C00O 0.0283(16) 0.0319(18) 0.0184(14) 0.0008(13) 0.0049(12) -0.0018(14) C00P 0.0174(13) 0.0164(15) 0.0187(13) -0.0007(11) 0.0053(11) -0.0010(11) C00Q 0.0310(17) 0.0348(19) 0.0181(15) -0.0027(13) 0.0065(13) 0.0010(14) C00R 0.0291(17) 0.0240(17) 0.0341(19) -0.0045(14) 0.0042(14) -0.0071(14) C00S 0.0227(15) 0.0291(18) 0.0233(16) -0.0070(14) 0.0016(13) -0.0006(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O003 S01 O004 119.05(14) . . ? O003 S01 N007 108.16(13) . . ? O003 S01 C00H 106.73(12) . . ? O004 S01 N007 106.70(12) . . ? O004 S01 C00H 107.97(15) . . ? N007 S01 C00H 107.78(15) . . ? C00A N006 H006 118.6 . . ? C00E N006 H006 118.6 . . ? C00E N006 C00A 122.7(2) . . ? C00M N007 S01 122.4(2) . . ? C00P N007 S01 124.8(2) . . ? C00P N007 C00M 111.8(2) . . ? C009 C008 H008 119.5 . . ? C009 C008 C00L 121.0(3) . . ? C00L C008 H008 119.5 . . ? C008 C009 C00A 117.8(3) . . ? C008 C009 C00B 118.9(3) . . ? C00B C009 C00A 123.3(3) . . ? N006 C00A C009 112.5(2) . . ? N006 C00A H00A 106.1 . . ? N006 C00A C00P 112.5(2) . . ? C009 C00A H00A 106.1 . . ? C009 C00A C00P 112.7(2) . . ? C00P C00A H00A 106.1 . . ? C009 C00B H00B 120.0 . . ? C00O C00B C009 120.0(3) . . ? C00O C00B H00B 120.0 . . ? C00D C00C Cl02 117.3(3) . . ? C00S C00C Cl02 119.8(2) . . ? C00S C00C C00D 122.9(3) . . ? C00C C00D H00D 120.3 . . ? C00C C00D C00E 119.4(3) . . ? C00E C00D H00D 120.3 . . ? N006 C00E C00D 122.4(3) . . ? N006 C00E C00I 119.7(3) . . ? C00I C00E C00D 117.8(3) . . ? O005 C00F C00K 126.5(3) . . ? O005 C00F C00P 123.5(3) . . ? C00K C00F C00P 109.9(3) . . ? H00C C00G H00E 109.5 . . ? H00C C00G H00F 109.5 . . ? H00E C00G H00F 109.5 . . ? C00H C00G H00C 109.5 . . ? C00H C00G H00E 109.5 . . ? C00H C00G H00F 109.5 . . ? C00G C00H S01 108.7(2) . . ? C00J C00H S01 105.9(2) . . ? C00J C00H C00G 111.4(2) . . ? C00N C00H S01 109.2(2) . . ? C00N C00H C00G 110.4(3) . . ? C00N C00H C00J 111.1(3) . . ? C00E C00I H00I 119.4 . . ? C00R C00I C00E 121.3(3) . . ? C00R C00I H00I 119.4 . . ? C00H C00J H00G 109.5 . . ? C00H C00J H00H 109.5 . . ? C00H C00J H00J 109.5 . . ? H00G C00J H00H 109.5 . . ? H00G C00J H00J 109.5 . . ? H00H C00J H00J 109.5 . . ? C00F C00K H00K 110.8 . . ? C00F C00K H00L 110.8 . . ? C00F C00K C00M 104.9(2) . . ? H00K C00K H00L 108.8 . . ? C00M C00K H00K 110.8 . . ? C00M C00K H00L 110.8 . . ? C008 C00L H00M 120.2 . . ? C00Q C00L C008 119.5(4) . . ? C00Q C00L H00M 120.2 . . ? N007 C00M C00K 102.4(2) . . ? N007 C00M H00N 111.3 . . ? N007 C00M H00O 111.3 . . ? C00K C00M H00N 111.3 . . ? C00K C00M H00O 111.3 . . ? H00N C00M H00O 109.2 . . ? C00H C00N H00P 109.5 . . ? C00H C00N H00Q 109.5 . . ? C00H C00N H00R 109.5 . . ? H00P C00N H00Q 109.5 . . ? H00P C00N H00R 109.5 . . ? H00Q C00N H00R 109.5 . . ? C00B C00O H00S 119.7 . . ? C00Q C00O C00B 120.5(3) . . ? C00Q C00O H00S 119.7 . . ? N007 C00P C00A 113.5(2) . . ? N007 C00P C00F 102.1(2) . . ? N007 C00P H00T 109.4 . . ? C00A C00P H00T 109.4 . . ? C00F C00P C00A 112.7(2) . . ? C00F C00P H00T 109.4 . . ? C00L C00Q H00U 120.0 . . ? C00O C00Q C00L 120.0(3) . . ? C00O C00Q H00U 120.0 . . ? C00I C00R H00V 119.5 . . ? C00I C00R C00S 121.1(3) . . ? C00S C00R H00V 119.5 . . ? C00C C00S C00R 117.5(3) . . ? C00C C00S H00W 121.2 . . ? C00R C00S H00W 121.2 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S01 O003 1.438(2) . ? S01 O004 1.439(2) . ? S01 N007 1.622(3) . ? S01 C00H 1.807(3) . ? Cl02 C00C 1.745(3) . ? O005 C00F 1.205(4) . ? N006 H006 0.8600 . ? N006 C00A 1.447(4) . ? N006 C00E 1.377(4) . ? N007 C00M 1.488(4) . ? N007 C00P 1.468(4) . ? C008 H008 0.9300 . ? C008 C009 1.389(4) . ? C008 C00L 1.391(5) . ? C009 C00A 1.512(4) . ? C009 C00B 1.397(4) . ? C00A H00A 0.9800 . ? C00A C00P 1.565(4) . ? C00B H00B 0.9300 . ? C00B C00O 1.389(5) . ? C00C C00D 1.385(4) . ? C00C C00S 1.377(5) . ? C00D H00D 0.9300 . ? C00D C00E 1.412(4) . ? C00E C00I 1.400(4) . ? C00F C00K 1.500(4) . ? C00F C00P 1.525(4) . ? C00G H00C 0.9600 . ? C00G H00E 0.9600 . ? C00G H00F 0.9600 . ? C00G C00H 1.532(5) . ? C00H C00J 1.529(5) . ? C00H C00N 1.525(4) . ? C00I H00I 0.9300 . ? C00I C00R 1.379(5) . ? C00J H00G 0.9600 . ? C00J H00H 0.9600 . ? C00J H00J 0.9600 . ? C00K H00K 0.9700 . ? C00K H00L 0.9700 . ? C00K C00M 1.523(5) . ? C00L H00M 0.9300 . ? C00L C00Q 1.387(5) . ? C00M H00N 0.9700 . ? C00M H00O 0.9700 . ? C00N H00P 0.9600 . ? C00N H00Q 0.9600 . ? C00N H00R 0.9600 . ? C00O H00S 0.9300 . ? C00O C00Q 1.382(6) . ? C00P H00T 0.9800 . ? C00Q H00U 0.9300 . ? C00R H00V 0.9300 . ? C00R C00S 1.396(5) . ? C00S H00W 0.9300 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S01 N007 C00M C00K 160.7(2) . . . . ? S01 N007 C00P C00A 67.2(3) . . . . ? S01 N007 C00P C00F -171.2(2) . . . . ? Cl02 C00C C00D C00E -179.0(2) . . . . ? Cl02 C00C C00S C00R 179.2(3) . . . . ? O003 S01 N007 C00M 146.6(2) . . . . ? O003 S01 N007 C00P -20.9(3) . . . . ? O003 S01 C00H C00G 59.8(2) . . . . ? O003 S01 C00H C00J -60.0(2) . . . . ? O003 S01 C00H C00N -179.8(3) . . . . ? O004 S01 N007 C00M 17.4(3) . . . . ? O004 S01 N007 C00P -150.1(2) . . . . ? O004 S01 C00H C00G -171.1(2) . . . . ? O004 S01 C00H C00J 69.1(2) . . . . ? O004 S01 C00H C00N -50.7(3) . . . . ? O005 C00F C00K C00M 163.2(3) . . . . ? O005 C00F C00P N007 178.8(3) . . . . ? O005 C00F C00P C00A -59.0(4) . . . . ? N006 C00A C00P N007 -173.0(2) . . . . ? N006 C00A C00P C00F 71.5(3) . . . . ? N006 C00E C00I C00R -178.3(3) . . . . ? N007 S01 C00H C00G -56.2(2) . . . . ? N007 S01 C00H C00J -176.0(2) . . . . ? N007 S01 C00H C00N 64.3(3) . . . . ? C008 C009 C00A N006 135.8(3) . . . . ? C008 C009 C00A C00P -95.7(3) . . . . ? C008 C009 C00B C00O -1.6(5) . . . . ? C008 C00L C00Q C00O -1.9(5) . . . . ? C009 C008 C00L C00Q 0.8(5) . . . . ? C009 C00A C00P N007 58.5(3) . . . . ? C009 C00A C00P C00F -57.1(3) . . . . ? C009 C00B C00O C00Q 0.5(5) . . . . ? C00A N006 C00E C00D -4.0(4) . . . . ? C00A N006 C00E C00I 173.9(3) . . . . ? C00A C009 C00B C00O 178.4(3) . . . . ? C00B C009 C00A N006 -44.2(4) . . . . ? C00B C009 C00A C00P 84.3(4) . . . . ? C00B C00O C00Q C00L 1.2(5) . . . . ? C00C C00D C00E N006 178.0(3) . . . . ? C00C C00D C00E C00I 0.1(4) . . . . ? C00D C00C C00S C00R 0.1(5) . . . . ? C00D C00E C00I C00R -0.3(5) . . . . ? C00E N006 C00A C009 -150.9(3) . . . . ? C00E N006 C00A C00P 80.5(3) . . . . ? C00E C00I C00R C00S 0.5(6) . . . . ? C00F C00K C00M N007 27.1(3) . . . . ? C00H S01 N007 C00M -98.4(3) . . . . ? C00H S01 N007 C00P 94.2(3) . . . . ? C00I C00R C00S C00C -0.4(5) . . . . ? C00K C00F C00P N007 -1.5(3) . . . . ? C00K C00F C00P C00A 120.7(3) . . . . ? C00L C008 C009 C00A -179.1(3) . . . . ? C00L C008 C009 C00B 0.9(5) . . . . ? C00M N007 C00P C00A -101.5(3) . . . . ? C00M N007 C00P C00F 20.1(3) . . . . ? C00P N007 C00M C00K -30.4(3) . . . . ? C00P C00F C00K C00M -16.4(3) . . . . ? C00S C00C C00D C00E 0.0(5) . . . . ?