#------------------------------------------------------------------------------ #$Date: 2021-12-07 05:53:38 +0200 (Tue, 07 Dec 2021) $ #$Revision: 271222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158379.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_7158379 loop_ _publ_author_name 'Fuller, Rebecca O.' 'Taylor, Madeleine R.' 'Duggin, Margot' 'Bissember, Alex C.' 'Canty, Allan J.' 'Judd, Martyna M.' 'Cox, Nicholas' 'Moggach, Stephen A.' 'Turner, Gemma F.' _publ_section_title ; Enhanced synthesis of oxo-verdazyl radicals bearing sterically-and electronically-diverse C3-substituents. ; _journal_issue 46 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 10120 _journal_page_last 10138 _journal_paper_doi 10.1039/d1ob01946e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C13 H14 N4 O S2' _chemical_formula_sum 'C13 H14 N4 O S2' _chemical_formula_weight 306.40 _chemical_name_common 1,5-bis(thiophenyl)-2,4-dimethyl-carbohydrazide _chemical_name_systematic 1,5-bis(thiophenyl)-2,4-dimethyl-carbohydrazide _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-09-03 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _audit_update_record ; 2021-09-30 deposited with the CCDC. 2021-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.845(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.32320(10) _cell_length_b 19.6029(2) _cell_length_c 10.4905(2) _cell_measurement_reflns_used 13876 _cell_measurement_temperature 100.0(2) _cell_measurement_theta_max 75.1310 _cell_measurement_theta_min 4.4860 _cell_volume 1433.52(4) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _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 100.0(2) _diffrn_detector 'Hybrid photon' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.983 _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 24.00 118.00 0.50 0.05 -- 46.20 77.00 60.00 188 2 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00 120.00 188 3 \w 31.00 118.00 0.50 0.05 -- 46.20 57.00 90.00 174 4 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00 0.00 188 5 \w 34.00 121.00 0.50 0.05 -- 46.20 19.00 90.00 174 6 \w 31.00 118.00 0.50 0.05 -- 46.20 57.00 0.00 174 7 \w 31.00 118.00 0.50 0.05 -- 46.20 57.00 -60.00 174 8 \w 31.00 118.00 0.50 0.05 -- 46.20 57.00-120.00 174 9 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00-150.00 188 10 \w 56.00 118.00 0.50 0.05 -- 46.20 151.00-133.00 124 11 \w 56.00 164.00 0.50 0.08 -- 102.41 151.00-133.00 216 12 \w 86.00 175.00 0.50 0.08 -- 102.41 61.00-150.00 178 13 \w 76.00 175.00 0.50 0.08 -- 102.41 122.00 65.00 198 14 \w 74.00 175.00 0.50 0.08 -- 102.41 125.00 120.00 202 15 \w 90.00 177.00 0.50 0.08 -- 102.41 30.00 150.00 174 16 \w -28.00 26.00 0.50 0.05 -- 46.20 -19.00 120.00 108 17 \w 30.00 71.00 0.50 0.08 -- 102.41 -61.00 120.00 82 18 \w 30.00 71.00 0.50 0.08 -- 102.41 -61.00 30.00 82 19 \w 30.00 71.00 0.50 0.08 -- 102.41 -61.00 0.00 82 20 \w 30.00 71.00 0.50 0.08 -- 102.41 -61.00 -30.00 82 21 \w 30.00 105.00 0.50 0.08 -- 102.41 -77.00-180.00 150 22 \w 30.00 105.00 0.50 0.08 -- 102.41 -94.00-180.00 150 23 \w 26.00 109.00 0.50 0.05 -- 46.20-151.00-177.00 166 24 \w 30.00 130.00 0.50 0.08 -- 102.41-151.00-177.00 200 25 \w 30.00 111.00 0.50 0.08 -- 102.41-125.00-120.00 162 26 \w 30.00 111.00 0.50 0.08 -- 102.41-125.00 90.00 162 27 \w 11.00 92.00 0.50 0.05 -- 46.20-122.00 -15.00 162 28 \w 30.00 109.00 0.50 0.08 -- 102.41-122.00 -15.00 158 29 \w 30.00 105.00 0.50 0.08 -- 102.41 -94.00 0.00 150 30 \w -130.00 -30.00 0.50 0.08 -- -102.41 151.00-133.00 200 31 \w -111.00 -30.00 0.50 0.08 -- -102.41 125.00 150.00 162 32 \w -109.00 -30.00 0.50 0.08 -- -102.41 122.00 65.00 158 33 \w -92.00 -11.00 0.50 0.05 -- -46.20 122.00 65.00 162 34 \w -107.00 -30.00 0.50 0.08 -- -102.41 107.00-152.30 154 35 \w -175.00-123.00 0.50 0.08 -- -102.41 -80.00 120.37 104 36 \w -175.00 -79.00 0.50 0.08 -- -102.41 -79.00 18.53 192 37 \w -175.00 -80.00 0.50 0.08 -- -102.41 -77.00 0.00 190 38 \w -118.00 -23.00 0.50 0.05 -- -46.20 -77.00 -90.00 190 39 \w -175.00 -80.00 0.50 0.08 -- -102.41 -77.00-180.00 190 40 \w -118.00 -23.00 0.50 0.05 -- -46.20 -77.00-180.00 190 41 \w -175.00 -80.00 0.50 0.08 -- -102.41 -75.00 143.81 190 42 \w -175.00 -81.00 0.50 0.08 -- -102.41 -74.00 -62.19 188 43 \w -175.00 -84.00 0.50 0.08 -- -102.41 -65.00-158.59 182 44 \w -175.00 -86.00 0.50 0.08 -- -102.41 -62.00 24.34 178 45 \w -175.00 -86.00 0.50 0.08 -- -102.41 -61.00 60.00 178 46 \w -175.00 -89.00 0.50 0.08 -- -102.41 -51.00 72.72 172 47 \w -174.00 -90.00 0.50 0.08 -- -102.41 -45.00 90.00 168 48 \w -174.00 -90.00 0.50 0.08 -- -102.41 -45.00 -60.00 168 49 \w -177.00 -90.00 0.50 0.08 -- -102.41 -30.00-120.00 174 50 \w -118.00 -55.00 0.50 0.05 -- -46.20-151.00-177.00 126 51 \w -164.00 -55.00 0.50 0.08 -- -102.41-151.00-177.00 218 52 \w -118.00 -73.00 0.50 0.05 -- -46.20-125.00 30.00 90 53 \w -118.00 -73.00 0.50 0.05 -- -46.20-125.00-150.00 90 54 \w -175.00 -75.00 0.50 0.08 -- -102.41-122.00 -15.00 200 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0912886000 _diffrn_orient_matrix_UB_12 0.0709547000 _diffrn_orient_matrix_UB_13 -0.0372384000 _diffrn_orient_matrix_UB_21 0.2007438000 _diffrn_orient_matrix_UB_22 0.0328367000 _diffrn_orient_matrix_UB_23 0.0453401000 _diffrn_orient_matrix_UB_31 0.0144310000 _diffrn_orient_matrix_UB_32 -0.0080908000 _diffrn_orient_matrix_UB_33 -0.1426495000 _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 0.0754 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 21491 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.509 _diffrn_reflns_theta_min 4.511 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.380 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.64386 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.420 _exptl_crystal_description block _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.262 _exptl_crystal_size_mid 0.117 _exptl_crystal_size_min 0.086 _refine_diff_density_max 0.282 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 93 _refine_ls_number_reflns 1468 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.137 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0317 _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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1202 _refine_ls_wR_factor_ref 0.1228 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1426 _reflns_number_total 1468 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01946e2.cif _cod_data_source_block 11b _cod_depositor_comments 'Adding full bibliography for 7158376--7158384.cif.' _cod_database_code 7158379 _chemical_oxdiff_formula 'C13 H14 N4 O S2' _chemical_oxdiff_usercomment 'Becky UTas' _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 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C005(H005), C008(H008), C00A(H00D), C00B(H00E) 2.b Idealised Me refined as rotating group: C009(H00A,H00B,H00C) ; _shelx_res_file ; TITL bof3_a.res in C2/c bof3.res created by SHELXL-2018/3 at 13:17:50 on 03-Sep-2020 REM Old TITL BOF3 in C2/c REM SHELXT solution in C2/c: R1 0.086, Rweak 0.006, Alpha 0.019 REM 0.463 for 44 systematic absences, Orientation as input REM Formula found by SHELXT: C13 N4 O S2 CELL 1.54184 7.3232 19.6029 10.4905 90 107.845 90 ZERR 4 0.0001 0.0002 0.0002 0 0.002 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O S UNIT 52 56 16 4 8 L.S. 4 0 0 PLAN 1 CONF BOND list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.100000 FVAR 0.32024 S001 5 0.217605 0.581171 0.667556 11.00000 0.02696 0.01816 = 0.01548 -0.00057 0.00709 0.00408 O002 4 0.500000 0.274189 0.750000 10.50000 0.03540 0.01142 = 0.02193 0.00000 0.01050 0.00000 N003 3 0.424150 0.372999 0.632337 11.00000 0.02260 0.01183 = 0.01571 -0.00034 0.00614 0.00177 N004 3 0.357796 0.438484 0.637118 11.00000 0.01810 0.01259 = 0.01833 -0.00175 0.00670 0.00024 C005 1 0.298586 0.471421 0.526041 11.00000 0.01827 0.01697 = 0.01466 -0.00164 0.00564 -0.00164 AFIX 43 H005 2 0.300693 0.450762 0.446698 11.00000 -1.20000 AFIX 0 C006 1 0.228686 0.540557 0.524231 11.00000 0.01552 0.01704 = 0.01478 -0.00076 0.00483 -0.00064 C007 1 0.500000 0.336956 0.750000 10.50000 0.01872 0.01491 = 0.01692 0.00000 0.00781 0.00000 C008 1 0.170050 0.583165 0.415451 11.00000 0.01859 0.02029 = 0.01638 0.00079 0.00493 0.00076 AFIX 43 H008 2 0.165428 0.570370 0.329151 11.00000 -1.20000 AFIX 0 C009 1 0.391251 0.337204 0.505120 11.00000 0.02427 0.01568 = 0.01713 -0.00435 0.00599 0.00005 AFIX 137 H00A 2 0.257201 0.338767 0.455674 11.00000 -1.50000 H00B 2 0.431181 0.290549 0.522009 11.00000 -1.50000 H00C 2 0.463752 0.358776 0.454082 11.00000 -1.50000 AFIX 0 C00A 1 0.117300 0.648778 0.448861 11.00000 0.02182 0.01976 = 0.02395 0.00510 0.00539 0.00385 AFIX 43 H00D 2 0.074257 0.683706 0.386917 11.00000 -1.20000 AFIX 0 C00B 1 0.136543 0.655031 0.581377 11.00000 0.02296 0.01730 = 0.02626 -0.00069 0.00690 0.00414 AFIX 43 H00E 2 0.108998 0.694673 0.620616 11.00000 -1.20000 AFIX 0 HKLF 4 REM bof3_a.res in C2/c REM wR2 = 0.1228, GooF = S = 1.137, Restrained GooF = 1.137 for all data REM R1 = 0.0317 for 1426 Fo > 4sig(Fo) and 0.0323 for all 1468 data REM 93 parameters refined using 0 restraints END WGHT 0.0506 1.1696 REM Highest difference peak 0.282, deepest hole -0.394, 1-sigma level 0.062 Q1 1 0.2288 0.5564 0.5791 11.00000 0.05 0.28 ; _shelx_res_checksum 93504 _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 2.385 _oxdiff_exptl_absorpt_empirical_full_min 0.653 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 S001 S 0.21761(4) 0.58117(2) 0.66756(3) 0.0201(2) Uani 1 1 d . . . . . O002 O 0.500000 0.27419(6) 0.750000 0.0225(3) Uani 1 2 d S T P . . N003 N 0.42415(14) 0.37300(5) 0.63234(9) 0.0166(3) Uani 1 1 d . . . . . N004 N 0.35780(13) 0.43848(5) 0.63712(10) 0.0161(3) Uani 1 1 d . . . . . C005 C 0.29859(15) 0.47142(6) 0.52604(12) 0.0165(3) Uani 1 1 d . . . . . H005 H 0.300693 0.450762 0.446698 0.020 Uiso 1 1 calc R U . . . C006 C 0.22869(16) 0.54056(6) 0.52423(11) 0.0157(3) Uani 1 1 d . . . . . C007 C 0.500000 0.33696(8) 0.750000 0.0163(4) Uani 1 2 d S T P . . C008 C 0.17005(17) 0.58316(6) 0.41545(14) 0.0185(3) Uani 1 1 d . . . . . H008 H 0.165428 0.570370 0.329151 0.022 Uiso 1 1 calc R U . . . C009 C 0.39125(19) 0.33720(6) 0.50512(13) 0.0191(3) Uani 1 1 d . . . . . H00A H 0.257201 0.338767 0.455674 0.029 Uiso 1 1 calc R U . . . H00B H 0.431181 0.290549 0.522009 0.029 Uiso 1 1 calc R U . . . H00C H 0.463752 0.358776 0.454082 0.029 Uiso 1 1 calc R U . . . C00A C 0.11730(18) 0.64878(7) 0.44886(14) 0.0222(3) Uani 1 1 d . . . . . H00D H 0.074257 0.683706 0.386917 0.027 Uiso 1 1 calc R U . . . C00B C 0.13654(18) 0.65503(6) 0.58138(14) 0.0223(3) Uani 1 1 d . . . . . H00E H 0.108998 0.694673 0.620616 0.027 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 S001 0.0270(3) 0.0182(3) 0.0155(3) -0.00057(9) 0.00709(19) 0.00408(9) O002 0.0354(7) 0.0114(6) 0.0219(7) 0.000 0.0105(6) 0.000 N003 0.0226(5) 0.0118(5) 0.0157(6) -0.0003(4) 0.0061(4) 0.0018(4) N004 0.0181(5) 0.0126(5) 0.0183(6) -0.0018(4) 0.0067(4) 0.0002(4) C005 0.0183(5) 0.0170(6) 0.0147(6) -0.0016(4) 0.0056(4) -0.0016(4) C006 0.0155(5) 0.0170(6) 0.0148(6) -0.0008(4) 0.0048(5) -0.0006(4) C007 0.0187(8) 0.0149(8) 0.0169(9) 0.000 0.0078(7) 0.000 C008 0.0186(6) 0.0203(7) 0.0164(7) 0.0008(4) 0.0049(5) 0.0008(4) C009 0.0243(6) 0.0157(6) 0.0171(6) -0.0044(5) 0.0060(5) 0.0000(4) C00A 0.0218(6) 0.0198(7) 0.0240(8) 0.0051(5) 0.0054(6) 0.0038(5) C00B 0.0230(6) 0.0173(6) 0.0263(8) -0.0007(5) 0.0069(6) 0.0041(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -5 0 0 0.0556 4 -4 0 0.0559 -3 10 0 0.0460 3 -10 -1 0.0470 -1 12 0 0.0441 0 -13 -1 0.0388 2 12 0 0.0437 -1 -12 0 0.0420 3 10 0 0.0535 -3 -10 0 0.0497 4 7 0 0.0571 -3 -7 -3 0.0741 -4 -4 0 0.0570 2 -1 -7 0.1311 -4 8 0 0.0513 4 -8 0 0.0552 -2 1 7 0.1197 -1 12 -1 0.0418 1 -12 0 0.0420 0 13 -1 0.0399 -2 -12 0 0.0456 2 12 -1 0.0456 3 6 -5 0.1035 4 1 -6 0.1130 4 4 0 0.0571 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 C00B S001 C006 91.80(6) . . ? N004 N003 C007 119.53(10) . . ? N004 N003 C009 121.27(9) . . ? C007 N003 C009 118.61(11) . . ? C005 N004 N003 117.34(10) . . ? N004 C005 H005 119.9 . . ? N004 C005 C006 120.13(11) . . ? C006 C005 H005 119.9 . . ? C005 C006 S001 122.13(9) . . ? C008 C006 S001 110.95(9) . . ? C008 C006 C005 126.89(11) . . ? O002 C007 N003 120.74(7) . 2_656 ? O002 C007 N003 120.74(7) . . ? N003 C007 N003 118.53(15) . 2_656 ? C006 C008 H008 123.6 . . ? C006 C008 C00A 112.71(12) . . ? C00A C008 H008 123.6 . . ? N003 C009 H00A 109.5 . . ? N003 C009 H00B 109.5 . . ? N003 C009 H00C 109.5 . . ? H00A C009 H00B 109.5 . . ? H00A C009 H00C 109.5 . . ? H00B C009 H00C 109.5 . . ? C008 C00A H00D 123.7 . . ? C00B C00A C008 112.58(12) . . ? C00B C00A H00D 123.7 . . ? S001 C00B H00E 124.0 . . ? C00A C00B S001 111.96(10) . . ? C00A C00B H00E 124.0 . . ? 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 S001 C006 1.7251(12) . ? S001 C00B 1.7138(13) . ? O002 C007 1.230(2) . ? N003 N004 1.3789(14) . ? N003 C007 1.3824(13) . ? N003 C009 1.4610(15) . ? N004 C005 1.2857(16) . ? C005 H005 0.9300 . ? C005 C006 1.4468(16) . ? C006 C008 1.3726(18) . ? C008 H008 0.9300 . ? C008 C00A 1.4175(16) . ? C009 H00A 0.9600 . ? C009 H00B 0.9600 . ? C009 H00C 0.9600 . ? C00A H00D 0.9300 . ? C00A C00B 1.359(2) . ? C00B H00E 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 S001 C006 C008 C00A 0.33(14) . . . . ? N003 N004 C005 C006 -179.47(9) . . . . ? N004 N003 C007 O002 155.22(7) . . . . ? N004 N003 C007 N003 -24.78(7) . . . 2_656 ? N004 C005 C006 S001 -1.06(15) . . . . ? N004 C005 C006 C008 176.54(12) . . . . ? C005 C006 C008 C00A -177.49(11) . . . . ? C006 S001 C00B C00A 0.48(11) . . . . ? C006 C008 C00A C00B 0.03(17) . . . . ? C007 N003 N004 C005 176.15(9) . . . . ? C008 C00A C00B S001 -0.38(15) . . . . ? C009 N003 N004 C005 -12.77(16) . . . . ? C009 N003 C007 O002 -16.10(11) . . . . ? C009 N003 C007 N003 163.90(11) . . . 2_656 ? C00B S001 C006 C005 177.48(10) . . . . ? C00B S001 C006 C008 -0.46(10) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -4.6034 0.3038 0.4121 0.4265 -0.8955 -0.1277 4.3568 -4.1990 -0.4497 -0.6789 0.7163 0.1610 -2.5955 10.4005 -0.0459 0.9766 -0.1816 -0.1151 2.7517 -10.3377 -0.7740 -0.9559 0.1778 0.2338 -1.3485 12.1471 0.0184 0.9843 0.1290 -0.1204 0.1013 -12.6753 -0.5834 -0.8869 -0.4223 0.1872 1.5222 12.0298 -0.2871 0.7253 0.6876 -0.0344 -1.4357 -12.0588 -0.0328 -0.7233 -0.6857 0.0815 2.5986 10.2353 0.3661 0.4754 0.8744 -0.0975 -2.5822 -10.2376 -0.4211 -0.4750 -0.8736 0.1056 3.6022 7.3888 0.3484 0.1825 0.9815 -0.0575 -2.7803 -7.2823 -2.5058 -0.1696 -0.9109 0.3763 -4.2876 -3.7659 -0.1567 0.1300 -0.9915 -0.0090 1.7005 -1.3170 -6.7632 0.0032 -0.0085 1.0000 -3.5153 7.6032 -0.4640 0.8777 -0.4771 -0.0461 3.5638 -7.6301 0.2477 -0.8759 0.4761 0.0778 -1.7159 1.2206 6.7671 -0.0087 0.0024 -1.0000 -1.1626 12.0892 -0.7399 0.9915 0.1300 -0.0090 1.3142 -12.1483 0.1242 -0.9866 -0.1295 0.0995 0.2136 12.6654 -0.6333 0.9028 0.4301 -0.0090 -1.5673 -12.0031 0.4588 -0.7257 -0.6880 0.0090 1.6389 11.9429 -0.7400 0.7253 0.6876 0.0326 3.1726 6.0155 -5.1231 0.3280 0.6021 0.7279 3.5166 0.5938 -5.8952 -0.0594 0.4581 0.8869 4.3649 3.6970 -0.1711 -0.1298 0.9899 0.0575