#------------------------------------------------------------------------------ #$Date: 2023-01-26 03:37:15 +0200 (Thu, 26 Jan 2023) $ #$Revision: 280616 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159120.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_7159120 loop_ _publ_author_name 'Li, Yarui' 'Huang, Xiaoxia' 'Peng, Shiyong' 'Wang, Jian' 'Lang, Ming' _publ_section_title ; N-Heterocyclic Carbene-Catalyzed [3 + 3] Cycloaddition of \a-Bromoenals with \b-Nitro Enamines: Synthesis of Nitro-containing \d-Lactams ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D2OB02334B _journal_year 2023 _chemical_formula_moiety 'C18 H15 F N2 O3 S' _chemical_formula_sum 'C18 H15 F N2 O3 S' _chemical_formula_weight 358.38 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-07-21 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _audit_update_record ; 2022-12-28 deposited with the CCDC. 2023-01-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 8.17910(10) _cell_length_b 19.9839(3) _cell_length_c 20.2957(3) _cell_measurement_reflns_used 8521 _cell_measurement_temperature 298.98(10) _cell_measurement_theta_max 77.0520 _cell_measurement_theta_min 4.3720 _cell_volume 3317.34(8) _computing_cell_refinement 'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)' _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 air _diffrn_ambient_temperature 298.98(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.934 _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 37.00 62.00 0.50 0.46 -- 108.86 -57.00 150.00 50 2 \w 40.00 65.00 0.50 0.46 -- 108.86 -57.00 120.00 50 3 \w 39.00 64.00 0.50 0.46 -- 108.86 -57.00 60.00 50 4 \w 37.00 62.00 0.50 0.46 -- 108.86 -57.00 -60.00 50 5 \w 38.00 63.00 0.50 0.46 -- 108.86 -57.00 -90.00 50 6 \w 41.00 66.00 0.50 0.46 -- 108.86 -57.00-120.00 50 7 \w 109.00 178.00 0.50 0.46 -- 108.86 88.00 -9.00 138 8 \w -71.00 -3.00 0.50 0.12 -- -48.55 82.00-112.00 136 9 \w -66.00 -32.00 0.50 0.46 -- -91.75 57.00 -60.00 68 10 \w -61.00 -19.00 0.50 0.46 -- -91.75 57.00 60.00 84 11 \w -157.00 -79.00 0.50 0.46 -- -91.75 -55.00 -15.00 156 12 \w -138.00 -90.00 0.50 0.46 -- -91.75 -82.00 126.00 96 13 \w -114.00 -87.00 0.50 0.12 -- -48.55-125.00 30.00 54 14 \w -119.00 -74.00 0.50 0.12 -- -48.55-125.00 -90.00 90 15 \w -121.00 -81.00 0.50 0.12 -- -48.55-125.00-120.00 80 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0686793000 _diffrn_orient_matrix_UB_12 -0.0666478000 _diffrn_orient_matrix_UB_13 0.0262076000 _diffrn_orient_matrix_UB_21 -0.1033737000 _diffrn_orient_matrix_UB_22 -0.0077380000 _diffrn_orient_matrix_UB_23 -0.0630323000 _diffrn_orient_matrix_UB_31 0.1416964000 _diffrn_orient_matrix_UB_32 -0.0379510000 _diffrn_orient_matrix_UB_33 -0.0331964000 _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 0.0329 _diffrn_reflns_av_unetI/netI 0.0294 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.934 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 12990 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.934 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.372 _diffrn_reflns_theta_min 4.357 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.015 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.69836 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021) 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 1.435 _exptl_crystal_description block _exptl_crystal_F_000 1488 _refine_diff_density_max 0.178 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.036 _refine_ls_extinction_coef 0.00106(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3297 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0349 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+0.7843P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.0986 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2917 _reflns_number_total 3297 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2ob02334b2.cif _cod_data_source_block exp_3718_auto _cod_database_code 7159120 _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 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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: C00B(H00B) 2.b Secondary CH2 refined with riding coordinates: C00H(H00A,H00D) 2.c Aromatic/amide H refined with riding coordinates: C00C(H00C), C00F(H00F), C00G(H00G), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P) 2.d Idealised Me refined as rotating group: C00L(H00E,H00H,H00I) ; _shelx_res_file ; TITL exp_3718_auto_a.res in Pbca exp_3718_auto.res created by SHELXL-2018/3 at 10:53:52 on 21-Jul-2022 REM Old TITL exp_3718_auto in Pbca REM SHELXT solution in Pbca: R1 0.148, Rweak 0.061, Alpha 0.014 REM 0.487 for 443 systematic absences, Orientation as input REM Formula found by SHELXT: C19 N2 O3 Cl CELL 1.54184 8.1791 19.9839 20.2957 90 90 90 ZERR 8 0.0001 0.0003 0.0003 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 F N O S UNIT 144 120 8 16 24 8 L.S. 4 0 0 PLAN 5 TEMP 26 CONF list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.046700 0.784300 EXTI 0.001055 FVAR 0.43154 S01 6 0.072421 0.691028 0.442111 11.00000 0.05432 0.05633 = 0.04014 0.00180 0.00702 -0.00800 F002 3 0.475841 0.468930 0.295833 11.00000 0.07342 0.03633 = 0.10255 -0.00293 0.01203 0.00453 O003 5 0.381517 0.754362 0.238512 11.00000 0.08306 0.04966 = 0.04292 0.00020 0.01750 -0.00064 N004 4 0.247879 0.726402 0.333003 11.00000 0.04150 0.03708 = 0.03384 -0.00055 -0.00019 0.00142 O005 5 0.139319 0.791199 0.520762 11.00000 0.08188 0.07054 = 0.04246 -0.00635 0.01409 -0.00229 O006 5 0.171853 0.893983 0.490619 11.00000 0.06745 0.05838 = 0.06501 -0.02388 0.00614 0.00085 N007 4 0.171433 0.833267 0.478414 11.00000 0.03814 0.05566 = 0.04697 -0.01326 0.00041 0.00185 C008 1 0.301919 0.658050 0.324562 11.00000 0.03583 0.03679 = 0.03799 -0.00070 0.00067 -0.00081 C009 1 0.185881 0.747675 0.394558 11.00000 0.03304 0.04517 = 0.03429 -0.00093 -0.00095 0.00239 C00A 1 0.215961 0.811722 0.413917 11.00000 0.03305 0.04652 = 0.03972 -0.00513 -0.00028 0.00366 C00B 1 0.286842 0.864518 0.369460 11.00000 0.04155 0.03766 = 0.04546 -0.00263 -0.00331 0.00523 AFIX 13 H00B 2 0.223542 0.905435 0.377053 11.00000 -1.20000 AFIX 0 C00C 1 0.252716 0.622182 0.269792 11.00000 0.04113 0.04477 = 0.04165 -0.00280 -0.00363 -0.00334 AFIX 43 H00C 2 0.180546 0.641101 0.239679 11.00000 -1.20000 AFIX 0 C00D 1 0.463880 0.881031 0.385888 11.00000 0.04253 0.04135 = 0.04420 0.00433 0.00073 -0.00090 C00E 1 0.301986 0.772513 0.285529 11.00000 0.04917 0.04152 = 0.03522 0.00163 -0.00176 -0.00049 C00F 1 0.407820 0.630383 0.370099 11.00000 0.04427 0.04644 = 0.04373 -0.00134 -0.00651 0.00055 AFIX 43 H00F 2 0.440995 0.655078 0.406564 11.00000 -1.20000 AFIX 0 C00G 1 0.311451 0.557905 0.259977 11.00000 0.04951 0.04368 = 0.05319 -0.01052 0.00394 -0.00863 AFIX 43 H00G 2 0.281003 0.533295 0.223073 11.00000 -1.20000 AFIX 0 C00H 1 0.254721 0.843501 0.298226 11.00000 0.05455 0.04177 = 0.04348 0.00299 -0.00654 0.00363 AFIX 23 H00A 2 0.139452 0.849187 0.288479 11.00000 -1.20000 H00D 2 0.315956 0.872487 0.268888 11.00000 -1.20000 AFIX 0 C00I 1 0.415511 0.531576 0.306048 11.00000 0.04517 0.03272 = 0.06868 0.00215 0.01075 -0.00237 C00J 1 0.464284 0.565666 0.361126 11.00000 0.04981 0.04771 = 0.05871 0.00820 -0.00493 0.00570 AFIX 43 H00J 2 0.533618 0.545876 0.391774 11.00000 -1.20000 AFIX 0 C00K 1 0.588964 0.834913 0.378080 11.00000 0.04653 0.05187 = 0.05706 -0.00431 -0.00227 0.00475 AFIX 43 H00K 2 0.565847 0.792783 0.360990 11.00000 -1.20000 AFIX 0 C00L 1 -0.033247 0.641940 0.380946 11.00000 0.05688 0.06213 = 0.05700 0.00082 0.00555 -0.01992 AFIX 137 H00E 2 -0.050411 0.668538 0.342169 11.00000 -1.50000 H00H 2 -0.136892 0.627733 0.398182 11.00000 -1.50000 H00I 2 0.031294 0.603411 0.369918 11.00000 -1.50000 AFIX 0 C00M 1 0.502605 0.943216 0.411767 11.00000 0.05420 0.04196 = 0.09636 -0.00494 -0.00421 -0.00325 AFIX 43 H00M 2 0.420825 0.975109 0.416996 11.00000 -1.20000 AFIX 0 C00N 1 0.747716 0.850857 0.395421 11.00000 0.04239 0.07272 = 0.06853 0.00443 -0.00025 0.00552 AFIX 43 H00N 2 0.830607 0.819606 0.389336 11.00000 -1.20000 AFIX 0 C00O 1 0.783861 0.912315 0.421490 11.00000 0.04585 0.07271 = 0.08468 0.01471 -0.00463 -0.01518 AFIX 43 H00O 2 0.890742 0.922637 0.433372 11.00000 -1.20000 AFIX 0 C00P 1 0.661935 0.958534 0.429997 11.00000 0.06340 0.05413 = 0.11655 -0.00529 -0.00912 -0.01855 AFIX 43 H00P 2 0.685888 1.000194 0.447992 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_3718_auto_a.res in Pbca REM wR2 = 0.0986, GooF = S = 1.056, Restrained GooF = 1.056 for all data REM R1 = 0.0349 for 2917 Fo > 4sig(Fo) and 0.0392 for all 3297 data REM 228 parameters refined using 0 restraints END WGHT 0.0466 0.7882 REM Highest difference peak 0.178, deepest hole -0.183, 1-sigma level 0.036 Q1 1 0.1877 0.7803 0.4039 11.00000 0.05 0.18 Q2 1 0.2300 0.8378 0.3944 11.00000 0.05 0.18 Q3 1 0.2142 0.7380 0.3637 11.00000 0.05 0.18 Q4 1 0.3759 0.8748 0.3794 11.00000 0.05 0.18 Q5 1 0.4954 0.9215 0.3824 11.00000 0.05 0.17 ; _shelx_res_checksum 77359 _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 1.420 _oxdiff_exptl_absorpt_empirical_full_min 0.781 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' '-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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S01 S 0.07242(5) 0.69103(2) 0.44211(2) 0.05026(15) Uani 1 1 d . . . . . F002 F 0.47584(14) 0.46893(5) 0.29583(6) 0.0708(3) Uani 1 1 d . . . . . O003 O 0.38152(17) 0.75436(6) 0.23851(5) 0.0585(3) Uani 1 1 d . . . . . N004 N 0.24788(14) 0.72640(6) 0.33300(5) 0.0375(3) Uani 1 1 d . . . . . O005 O 0.13932(18) 0.79120(7) 0.52076(6) 0.0650(4) Uani 1 1 d . . . . . O006 O 0.17185(17) 0.89398(6) 0.49062(6) 0.0636(3) Uani 1 1 d . . . . . N007 N 0.17143(15) 0.83327(7) 0.47841(7) 0.0469(3) Uani 1 1 d . . . . . C008 C 0.30192(17) 0.65805(7) 0.32456(7) 0.0369(3) Uani 1 1 d . . . . . C009 C 0.18588(16) 0.74767(7) 0.39456(7) 0.0375(3) Uani 1 1 d . . . . . C00A C 0.21596(17) 0.81172(7) 0.41392(7) 0.0398(3) Uani 1 1 d . . . . . C00B C 0.28684(18) 0.86452(7) 0.36946(7) 0.0416(3) Uani 1 1 d . . . . . H00B H 0.223542 0.905435 0.377053 0.050 Uiso 1 1 calc R U . . . C00C C 0.25272(18) 0.62218(7) 0.26979(7) 0.0425(3) Uani 1 1 d . . . . . H00C H 0.180546 0.641101 0.239679 0.051 Uiso 1 1 calc R U . . . C00D C 0.46388(18) 0.88103(7) 0.38589(7) 0.0427(3) Uani 1 1 d . . . . . C00E C 0.30199(19) 0.77251(7) 0.28553(7) 0.0420(3) Uani 1 1 d . . . . . C00F C 0.40782(19) 0.63038(8) 0.37010(8) 0.0448(3) Uani 1 1 d . . . . . H00F H 0.440995 0.655078 0.406564 0.054 Uiso 1 1 calc R U . . . C00G C 0.3115(2) 0.55791(8) 0.25998(8) 0.0488(4) Uani 1 1 d . . . . . H00G H 0.281003 0.533295 0.223073 0.059 Uiso 1 1 calc R U . . . C00H C 0.2547(2) 0.84350(7) 0.29823(7) 0.0466(4) Uani 1 1 d . . . . . H00A H 0.139452 0.849187 0.288479 0.056 Uiso 1 1 calc R U . . . H00D H 0.315956 0.872487 0.268888 0.056 Uiso 1 1 calc R U . . . C00I C 0.41551(19) 0.53158(7) 0.30605(9) 0.0489(4) Uani 1 1 d . . . . . C00J C 0.4643(2) 0.56567(8) 0.36113(9) 0.0521(4) Uani 1 1 d . . . . . H00J H 0.533618 0.545876 0.391774 0.062 Uiso 1 1 calc R U . . . C00K C 0.5890(2) 0.83491(9) 0.37808(9) 0.0518(4) Uani 1 1 d . . . . . H00K H 0.565847 0.792783 0.360990 0.062 Uiso 1 1 calc R U . . . C00L C -0.0332(2) 0.64194(9) 0.38095(9) 0.0587(4) Uani 1 1 d . . . . . H00E H -0.050411 0.668538 0.342169 0.088 Uiso 1 1 calc R U . . . H00H H -0.136892 0.627733 0.398182 0.088 Uiso 1 1 calc R U . . . H00I H 0.031294 0.603411 0.369918 0.088 Uiso 1 1 calc R U . . . C00M C 0.5026(2) 0.94322(9) 0.41177(11) 0.0642(5) Uani 1 1 d . . . . . H00M H 0.420825 0.975109 0.416996 0.077 Uiso 1 1 calc R U . . . C00N C 0.7477(2) 0.85086(10) 0.39542(10) 0.0612(5) Uani 1 1 d . . . . . H00N H 0.830607 0.819606 0.389336 0.073 Uiso 1 1 calc R U . . . C00O C 0.7839(2) 0.91232(10) 0.42149(11) 0.0677(5) Uani 1 1 d . . . . . H00O H 0.890742 0.922637 0.433372 0.081 Uiso 1 1 calc R U . . . C00P C 0.6619(3) 0.95853(10) 0.43000(13) 0.0780(6) Uani 1 1 d . . . . . H00P H 0.685888 1.000194 0.447992 0.094 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 0.0543(3) 0.0563(3) 0.0401(2) 0.00180(16) 0.00702(16) -0.00800(17) F002 0.0734(7) 0.0363(5) 0.1026(9) -0.0029(5) 0.0120(6) 0.0045(5) O003 0.0831(9) 0.0497(6) 0.0429(6) 0.0002(5) 0.0175(6) -0.0006(6) N004 0.0415(6) 0.0371(6) 0.0338(5) -0.0005(5) -0.0002(5) 0.0014(5) O005 0.0819(9) 0.0705(8) 0.0425(6) -0.0063(6) 0.0141(6) -0.0023(7) O006 0.0674(8) 0.0584(7) 0.0650(8) -0.0239(6) 0.0061(6) 0.0009(6) N007 0.0381(6) 0.0557(8) 0.0470(7) -0.0133(6) 0.0004(5) 0.0019(6) C008 0.0358(7) 0.0368(7) 0.0380(7) -0.0007(5) 0.0007(5) -0.0008(5) C009 0.0330(6) 0.0452(7) 0.0343(7) -0.0009(6) -0.0010(5) 0.0024(6) C00A 0.0331(7) 0.0465(8) 0.0397(7) -0.0051(6) -0.0003(6) 0.0037(6) C00B 0.0415(8) 0.0377(7) 0.0455(8) -0.0026(6) -0.0033(6) 0.0052(6) C00C 0.0411(8) 0.0448(8) 0.0416(7) -0.0028(6) -0.0036(6) -0.0033(6) C00D 0.0425(8) 0.0414(7) 0.0442(8) 0.0043(6) 0.0007(6) -0.0009(6) C00E 0.0492(8) 0.0415(7) 0.0352(7) 0.0016(6) -0.0018(6) -0.0005(6) C00F 0.0443(8) 0.0464(8) 0.0437(8) -0.0013(6) -0.0065(6) 0.0006(6) C00G 0.0495(9) 0.0437(8) 0.0532(9) -0.0105(7) 0.0039(7) -0.0086(7) C00H 0.0546(9) 0.0418(8) 0.0435(8) 0.0030(6) -0.0065(7) 0.0036(6) C00I 0.0452(8) 0.0327(7) 0.0687(10) 0.0022(7) 0.0107(7) -0.0024(6) C00J 0.0498(9) 0.0477(8) 0.0587(10) 0.0082(7) -0.0049(7) 0.0057(7) C00K 0.0465(9) 0.0519(9) 0.0571(9) -0.0043(7) -0.0023(7) 0.0047(7) C00L 0.0569(10) 0.0621(10) 0.0570(10) 0.0008(8) 0.0055(8) -0.0199(8) C00M 0.0542(10) 0.0420(9) 0.0964(14) -0.0049(9) -0.0042(10) -0.0033(7) C00N 0.0424(9) 0.0727(12) 0.0685(11) 0.0044(9) -0.0002(8) 0.0055(8) C00O 0.0459(10) 0.0727(12) 0.0847(14) 0.0147(11) -0.0046(9) -0.0152(9) C00P 0.0634(12) 0.0541(10) 0.1165(18) -0.0053(11) -0.0091(12) -0.0186(9) 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' F F 0.0727 0.0534 '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 C009 S01 C00L 103.06(7) . . ? C009 N004 C008 119.90(11) . . ? C00E N004 C008 116.24(11) . . ? C00E N004 C009 121.46(12) . . ? O005 N007 O006 122.02(13) . . ? O005 N007 C00A 119.31(13) . . ? O006 N007 C00A 118.62(14) . . ? C00C C008 N004 119.74(12) . . ? C00F C008 N004 119.36(12) . . ? C00F C008 C00C 120.84(13) . . ? N004 C009 S01 118.82(10) . . ? C00A C009 S01 122.95(11) . . ? C00A C009 N004 118.23(13) . . ? N007 C00A C00B 115.94(12) . . ? C009 C00A N007 120.19(13) . . ? C009 C00A C00B 123.77(13) . . ? C00A C00B H00B 106.7 . . ? C00A C00B C00D 112.78(12) . . ? C00A C00B C00H 107.96(12) . . ? C00D C00B H00B 106.7 . . ? C00D C00B C00H 115.49(13) . . ? C00H C00B H00B 106.7 . . ? C008 C00C H00C 120.2 . . ? C008 C00C C00G 119.68(14) . . ? C00G C00C H00C 120.2 . . ? C00K C00D C00B 122.21(14) . . ? C00M C00D C00B 119.66(14) . . ? C00M C00D C00K 118.09(15) . . ? O003 C00E N004 120.89(13) . . ? O003 C00E C00H 124.06(14) . . ? N004 C00E C00H 115.05(13) . . ? C008 C00F H00F 120.2 . . ? C008 C00F C00J 119.64(14) . . ? C00J C00F H00F 120.2 . . ? C00C C00G H00G 120.9 . . ? C00I C00G C00C 118.26(14) . . ? C00I C00G H00G 120.9 . . ? C00B C00H H00A 109.1 . . ? C00B C00H H00D 109.1 . . ? C00E C00H C00B 112.33(12) . . ? C00E C00H H00A 109.1 . . ? C00E C00H H00D 109.1 . . ? H00A C00H H00D 107.9 . . ? F002 C00I C00G 118.33(15) . . ? F002 C00I C00J 118.46(15) . . ? C00J C00I C00G 123.20(14) . . ? C00F C00J H00J 120.8 . . ? C00I C00J C00F 118.36(15) . . ? C00I C00J H00J 120.8 . . ? C00D C00K H00K 119.6 . . ? C00N C00K C00D 120.72(17) . . ? C00N C00K H00K 119.6 . . ? S01 C00L H00E 109.5 . . ? S01 C00L H00H 109.5 . . ? S01 C00L H00I 109.5 . . ? H00E C00L H00H 109.5 . . ? H00E C00L H00I 109.5 . . ? H00H C00L H00I 109.5 . . ? C00D C00M H00M 119.6 . . ? C00D C00M C00P 120.87(18) . . ? C00P C00M H00M 119.6 . . ? C00K C00N H00N 119.7 . . ? C00O C00N C00K 120.51(18) . . ? C00O C00N H00N 119.7 . . ? C00N C00O H00O 120.1 . . ? C00N C00O C00P 119.74(18) . . ? C00P C00O H00O 120.1 . . ? C00M C00P H00P 120.0 . . ? C00O C00P C00M 120.05(19) . . ? C00O C00P H00P 120.0 . . ? 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 C009 1.7533(15) . ? S01 C00L 1.8028(18) . ? F002 C00I 1.3615(17) . ? O003 C00E 1.2105(18) . ? N004 C008 1.4459(17) . ? N004 C009 1.4137(17) . ? N004 C00E 1.4048(18) . ? O005 N007 1.2306(18) . ? O006 N007 1.2384(17) . ? N007 C00A 1.4253(19) . ? C008 C00C 1.383(2) . ? C008 C00F 1.382(2) . ? C009 C00A 1.361(2) . ? C00A C00B 1.504(2) . ? C00B H00B 0.9800 . ? C00B C00D 1.522(2) . ? C00B C00H 1.528(2) . ? C00C H00C 0.9300 . ? C00C C00G 1.386(2) . ? C00D C00K 1.386(2) . ? C00D C00M 1.386(2) . ? C00E C00H 1.493(2) . ? C00F H00F 0.9300 . ? C00F C00J 1.385(2) . ? C00G H00G 0.9300 . ? C00G C00I 1.370(2) . ? C00H H00A 0.9700 . ? C00H H00D 0.9700 . ? C00I C00J 1.369(2) . ? C00J H00J 0.9300 . ? C00K H00K 0.9300 . ? C00K C00N 1.383(3) . ? C00L H00E 0.9600 . ? C00L H00H 0.9600 . ? C00L H00I 0.9600 . ? C00M H00M 0.9300 . ? C00M C00P 1.389(3) . ? C00N H00N 0.9300 . ? C00N C00O 1.370(3) . ? C00O H00O 0.9300 . ? C00O C00P 1.370(3) . ? C00P H00P 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 C009 C00A N007 7.43(19) . . . . ? S01 C009 C00A C00B -168.91(11) . . . . ? F002 C00I C00J C00F 177.50(14) . . . . ? O003 C00E C00H C00B -133.03(16) . . . . ? N004 C008 C00C C00G 176.61(13) . . . . ? N004 C008 C00F C00J -177.88(14) . . . . ? N004 C009 C00A N007 -173.21(12) . . . . ? N004 C009 C00A C00B 10.4(2) . . . . ? N004 C00E C00H C00B 46.64(19) . . . . ? O005 N007 C00A C009 15.7(2) . . . . ? O005 N007 C00A C00B -167.67(14) . . . . ? O006 N007 C00A C009 -166.76(14) . . . . ? O006 N007 C00A C00B 9.86(19) . . . . ? N007 C00A C00B C00D 76.54(16) . . . . ? N007 C00A C00B C00H -154.64(12) . . . . ? C008 N004 C009 S01 -34.85(16) . . . . ? C008 N004 C009 C00A 145.76(13) . . . . ? C008 N004 C00E O003 4.0(2) . . . . ? C008 N004 C00E C00H -175.64(12) . . . . ? C008 C00C C00G C00I 1.0(2) . . . . ? C008 C00F C00J C00I 1.5(2) . . . . ? C009 N004 C008 C00C 133.14(14) . . . . ? C009 N004 C008 C00F -49.55(18) . . . . ? C009 N004 C00E O003 166.42(14) . . . . ? C009 N004 C00E C00H -13.27(19) . . . . ? C009 C00A C00B C00D -106.97(16) . . . . ? C009 C00A C00B C00H 21.84(19) . . . . ? C00A C00B C00D C00K 65.81(19) . . . . ? C00A C00B C00D C00M -111.84(17) . . . . ? C00A C00B C00H C00E -48.74(17) . . . . ? C00B C00D C00K C00N -177.96(16) . . . . ? C00B C00D C00M C00P 177.05(19) . . . . ? C00C C008 C00F C00J -0.6(2) . . . . ? C00C C00G C00I F002 -178.74(14) . . . . ? C00C C00G C00I C00J -0.1(2) . . . . ? C00D C00B C00H C00E 78.53(17) . . . . ? C00D C00K C00N C00O 0.9(3) . . . . ? C00D C00M C00P C00O 1.1(4) . . . . ? C00E N004 C008 C00C -64.19(18) . . . . ? C00E N004 C008 C00F 113.11(15) . . . . ? C00E N004 C009 S01 163.41(11) . . . . ? C00E N004 C009 C00A -15.98(19) . . . . ? C00F C008 C00C C00G -0.7(2) . . . . ? C00G C00I C00J C00F -1.2(3) . . . . ? C00H C00B C00D C00K -59.0(2) . . . . ? C00H C00B C00D C00M 123.36(17) . . . . ? C00K C00D C00M C00P -0.7(3) . . . . ? C00K C00N C00O C00P -0.5(3) . . . . ? C00L S01 C009 N004 -33.81(13) . . . . ? C00L S01 C009 C00A 145.54(13) . . . . ? C00M C00D C00K C00N -0.3(3) . . . . ? C00N C00O C00P C00M -0.5(4) . . . . ?