#------------------------------------------------------------------------------ #$Date: 2021-11-02 03:50:02 +0200 (Tue, 02 Nov 2021) $ #$Revision: 270194 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158382.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_7158382 loop_ _publ_author_name 'Fuller, Rebecca Olivia' 'Taylor, Madeleine' 'Duggin, Margot' 'Bissember, Alex C.' 'Canty, Allan J.' 'Judd, Martyna' 'Cox, Nick' 'Moggach, Stephen A.' 'Turner, Gemma' _publ_section_title ; Enhanced Synthesis of oxo-Verdazyl Radicals Bearing Sterically-and Electronically-Diverse C3-Substitents ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01946E _journal_year 2021 _chemical_formula_moiety 'C20 H20 N4 O S, 0.5(H4 O2)' _chemical_formula_sum 'C20 H22 N4 O2 S' _chemical_formula_weight 382.49 _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_Hall '-P 2ac 2n' _space_group_name_H-M_alt 'P n m a' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-09-22 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-09-30 deposited with the CCDC. 2021-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.93100(10) _cell_length_b 19.1334(6) _cell_length_c 20.4301(6) _cell_measurement_reflns_used 4610 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 64.4070 _cell_measurement_theta_min 4.3070 _cell_volume 1927.51(9) _computing_cell_refinement 'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.103a (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 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.979 _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 -15.00 73.00 0.50 2.00 -- -2.66 22.00 61.00 176 2 \w 11.00 108.00 0.50 30.00 -- 83.35-111.00 64.00 194 3 \w 82.00 155.00 0.50 30.00 -- 83.35 111.00-108.00 146 4 \w -164.00 -76.00 0.50 30.00 -- -88.66 -22.00-104.00 176 5 \w -23.00 31.00 0.50 2.00 -- -2.66 -99.00 -90.00 108 6 \w -23.00 31.00 0.50 2.00 -- -2.66 -99.00-120.00 108 7 \w 11.00 66.00 0.50 30.00 -- 83.35 -57.00 150.00 110 8 \w 11.00 43.00 0.50 30.00 -- 83.35 -38.00-120.00 64 9 \w 11.00 43.00 0.50 30.00 -- 83.35 -38.00-150.00 64 10 \w 11.00 43.00 0.50 30.00 -- 83.35 -38.00 150.00 64 11 \w 11.00 66.00 0.50 30.00 -- 83.35 -57.00-150.00 110 12 \w 11.00 43.00 0.50 30.00 -- 83.35 -38.00 -30.00 64 13 \w -111.00 -16.00 0.50 30.00 -- -88.66 125.00 90.00 190 14 \w -66.00 -16.00 0.50 30.00 -- -88.66 57.00-180.00 100 15 \w -43.00 -16.00 0.50 30.00 -- -88.66 38.00 30.00 54 16 \w -43.00 -16.00 0.50 30.00 -- -88.66 38.00 60.00 54 17 \w -23.00 31.00 0.50 2.00 -- -2.66 -99.00 90.00 108 18 \w -74.00 12.00 0.50 2.00 -- -2.66 -57.00 90.00 172 19 \w -17.00 70.00 0.50 2.00 -- -2.66 57.00 -90.00 174 20 \w 71.00 150.00 0.50 30.00 -- 83.35 22.00 61.00 158 21 \w 71.00 158.00 0.50 30.00 -- 83.35 19.00 150.00 174 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0854417000 _diffrn_orient_matrix_UB_12 -0.0716726000 _diffrn_orient_matrix_UB_13 -0.0274885000 _diffrn_orient_matrix_UB_21 -0.0335089000 _diffrn_orient_matrix_UB_22 -0.0325794000 _diffrn_orient_matrix_UB_23 0.0684736000 _diffrn_orient_matrix_UB_31 -0.2987659000 _diffrn_orient_matrix_UB_32 -0.0168682000 _diffrn_orient_matrix_UB_33 -0.0154098000 _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 0.0703 _diffrn_reflns_av_unetI/netI 0.0410 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 13320 _diffrn_reflns_point_group_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 67.335 _diffrn_reflns_theta_max 67.335 _diffrn_reflns_theta_min 4.328 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.677 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84996 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.318 _exptl_crystal_description block _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.228 _exptl_crystal_size_mid 0.056 _exptl_crystal_size_min 0.046 _refine_diff_density_max 0.583 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.090 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.279 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 121 _refine_ls_number_reflns 1736 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.268 _refine_ls_R_factor_all 0.1463 _refine_ls_R_factor_gt 0.1355 _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^)+18.5821P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2605 _refine_ls_wR_factor_ref 0.2648 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1534 _reflns_number_total 1736 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01946e2.cif _cod_data_source_block bof21 _cod_database_code 7158382 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C10 H10 N4 O2 S' _chemical_oxdiff_usercomment 'Rebecca Fuller - Tasmania' _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 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 61.08 _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 O(H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C8) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(S2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2 Uanis(S2) = Uanis(C2) = Uanis(C5) = Uanis(C6) = Uanis(C8) 3. Others Fixed Sof: H16B(0.5) S2(0.5) C2(0.5) H2(0.5) C5(0.5) H5A(0.5) C6(0.5) H6(0.5) C8(0.5) 4.a Riding coordinates: N5(H5) 4.b Free rotating group: O16(H16A,H16B), S2(C2,C5,C6,C8) 4.c Ternary CH refined with riding coordinates: C4(H4) 4.d Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 4.e Aromatic/amide H refined with riding coordinates: C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C2(H2), C5(H5A), C6(H6) ; _shelx_res_file ; TITL bof21_a.res in P2(1)2(1)2(1) New:Pnma bof21.res created by SHELXL-2018/3 at 08:25:26 on 22-Sep-2021 REM TITL bof21_a.res in P2(1)2(1)2(1) New:Pnma CELL 1.54184 4.931 19.1334 20.4301 90 90 90 ZERR 4 0.0001 0.0006 0.0006 0 0 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5+Z SYMM +X,0.5-Y,+Z SYMM 0.5-X,-Y,0.5+Z SFAC C 2.310 20.844 1.02 10.208 1.589 0.569 0.865 51.651 0.216 0.018 0.009 = 8.99 0.77 12.011 SFAC H 0.493 10.511 0.323 26.126 0.14 3.142 0.041 57.8 0.003 0 0 0.07 0.32 = 1.008 SFAC N 12.213 0.006 3.132 9.893 2.013 28.997 1.166 0.583 -11.529 0.031 = 0.018 17.3 0.77 14.007 SFAC O 3.049 13.277 2.287 5.701 1.546 0.324 0.867 32.909 0.251 0.049 0.032 = 30.4 0.77 15.999 SFAC S 6.905 1.468 5.203 22.215 1.438 0.254 1.586 56.172 0.867 0.333 0.557 = 497 1.11 32.066 UNIT 80 88 16 8 4 EADP S2 C2 C5 C6 C8 ISOR C8 C6 C5 C2 S2 L.S. 4 0 0 PLAN 1 CONF MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.000000 18.582100 FVAR 0.74088 C4 1 0.360172 0.750000 0.451141 10.50000 0.01859 0.07102 = 0.01368 0.00000 0.00070 0.00000 AFIX 13 H4 2 0.535411 0.750000 0.428513 10.50000 -1.20000 AFIX 0 N5 3 0.346739 0.686795 0.490666 11.00000 0.01884 0.05487 = 0.02768 -0.00739 0.00048 0.00721 AFIX 3 H5 2 0.493869 0.677745 0.511616 11.00000 -1.20000 AFIX 0 N6 3 0.111436 0.689611 0.531649 11.00000 0.01682 0.03595 = 0.02831 -0.00332 -0.00070 -0.00261 C7 1 -0.005543 0.750000 0.551194 10.50000 0.02066 0.04745 = 0.01798 0.00000 -0.00154 0.00000 O8 4 -0.219343 0.750000 0.582808 10.50000 0.01966 0.04673 = 0.02016 0.00000 0.00395 0.00000 C9 1 0.014574 0.620836 0.552057 11.00000 0.02520 0.04280 = 0.04543 -0.00499 -0.00190 -0.01632 AFIX 23 H9A 2 -0.030930 0.593597 0.513548 11.00000 -1.20000 H9B 2 -0.149188 0.626410 0.577839 11.00000 -1.20000 AFIX 0 C10 1 0.223298 0.581608 0.591982 11.00000 0.01530 0.03137 = 0.04214 -0.00262 0.00427 -0.00666 C11 1 0.332207 0.611969 0.647763 11.00000 0.03223 0.03703 = 0.03429 -0.01187 0.00600 0.01095 AFIX 43 H11 2 0.278443 0.656588 0.660317 11.00000 -1.20000 AFIX 0 C12 1 0.520542 0.575860 0.684627 11.00000 0.03955 0.05947 = 0.03285 -0.00282 -0.00188 0.00692 AFIX 43 H12 2 0.590779 0.596071 0.722397 11.00000 -1.20000 AFIX 0 C13 1 0.605119 0.510452 0.666094 11.00000 0.02992 0.04830 = 0.05864 0.01261 0.00223 0.01061 AFIX 43 H13 2 0.732808 0.486421 0.690910 11.00000 -1.20000 AFIX 0 C14 1 0.499527 0.481107 0.610795 11.00000 0.03871 0.03986 = 0.10826 -0.02228 -0.01475 0.01336 AFIX 43 H14 2 0.554629 0.436591 0.598260 11.00000 -1.20000 AFIX 0 C15 1 0.313299 0.516376 0.573473 11.00000 0.03249 0.04345 = 0.08504 -0.03162 -0.01831 0.00052 AFIX 43 H15 2 0.247147 0.496076 0.535318 11.00000 -1.20000 AFIX 6 O16 4 -0.187918 0.750000 0.721069 10.50000 0.02822 0.09432 = 0.02259 0.00000 0.00297 0.00000 H16A 2 -0.347633 0.749971 0.734955 10.50000 -1.50000 H16B 2 -0.186380 0.759872 0.680509 10.50000 -1.50000 AFIX 6 PART -1 S2 5 0.022736 0.679464 0.366594 10.50000 0.02604 0.09207 = 0.03082 -0.02481 -0.00410 0.00574 C2 1 -0.192501 0.723936 0.314237 10.50000 0.02604 0.09207 = 0.03082 -0.02481 -0.00410 0.00574 AFIX 43 H2 2 -0.306812 0.702681 0.283993 10.50000 -1.20000 AFIX 5 C5 1 -0.171750 0.794875 0.323371 10.50000 0.02604 0.09207 = 0.03082 -0.02481 -0.00410 0.00574 AFIX 43 H5A 2 -0.272668 0.827507 0.300027 10.50000 -1.20000 AFIX 5 C6 1 0.019899 0.812974 0.372172 10.50000 0.02604 0.09207 = 0.03082 -0.02481 -0.00410 0.00574 AFIX 43 H6 2 0.058824 0.858778 0.384161 10.50000 -1.20000 AFIX 5 C8 1 0.140487 0.756403 0.399529 10.50000 0.02604 0.09207 = 0.03082 -0.02481 -0.00410 0.00574 AFIX 0 HKLF 4 REM bof21_a.res in P2(1)2(1)2(1) New:Pnma REM wR2 = 0.264778, GooF = S = 1.27908, Restrained GooF = 1.26798 for all data REM R1 = 0.135538 for 1534 Fo > 4sig(Fo) and 0.146312 for all 1736 data REM 121 parameters refined using 30 restraints END WGHT 0.0000 18.5825 REM Highest difference peak 0.583, deepest hole -0.405, 1-sigma level 0.090 Q1 1 -0.1736 0.7500 0.3167 10.50000 0.05 0.56 ; _shelx_res_checksum 48562 _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 2.360 _oxdiff_exptl_absorpt_empirical_full_min 0.567 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x, -y+1/2, z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z-1/2' '-x, y-1/2, -z' 'x-1/2, y, -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 C4 C 0.360(2) 0.750000 0.4511(4) 0.034(3) Uani 1 2 d S T P . . H4 H 0.535411 0.750000 0.428513 0.041 Uiso 1 2 calc R U P A . N5 N 0.3467(11) 0.6868(3) 0.4907(3) 0.0338(14) Uani 1 1 d . . . . . H5 H 0.493869 0.677745 0.511616 0.041 Uiso 1 1 d R U . . . N6 N 0.1114(11) 0.6896(3) 0.5316(2) 0.0270(13) Uani 1 1 d . . . . . C7 C -0.006(2) 0.750000 0.5512(4) 0.029(2) Uani 1 2 d S T P . . O8 O -0.2193(13) 0.750000 0.5828(3) 0.0289(15) Uani 1 2 d S T P . . C9 C 0.0146(15) 0.6208(4) 0.5521(4) 0.0378(18) Uani 1 1 d . . . . . H9A H -0.030930 0.593597 0.513548 0.045 Uiso 1 1 calc R U . . . H9B H -0.149188 0.626410 0.577839 0.045 Uiso 1 1 calc R U . . . C10 C 0.2233(13) 0.5816(3) 0.5920(3) 0.0296(15) Uani 1 1 d . . . . . C11 C 0.3322(15) 0.6120(4) 0.6478(3) 0.0345(17) Uani 1 1 d . . . . . H11 H 0.278443 0.656588 0.660317 0.041 Uiso 1 1 calc R U . . . C12 C 0.5205(16) 0.5759(4) 0.6846(4) 0.044(2) Uani 1 1 d . . . . . H12 H 0.590779 0.596071 0.722397 0.053 Uiso 1 1 calc R U . . . C13 C 0.6051(16) 0.5105(4) 0.6661(4) 0.046(2) Uani 1 1 d . . . . . H13 H 0.732808 0.486421 0.690910 0.055 Uiso 1 1 calc R U . . . C14 C 0.4995(18) 0.4811(4) 0.6108(5) 0.062(3) Uani 1 1 d . . . . . H14 H 0.554629 0.436591 0.598260 0.075 Uiso 1 1 calc R U . . . C15 C 0.3133(16) 0.5164(4) 0.5735(5) 0.054(2) Uani 1 1 d . . . . . H15 H 0.247147 0.496076 0.535318 0.064 Uiso 1 1 calc R U . . . O16 O -0.1879(16) 0.750000 0.7211(3) 0.048(2) Uani 1 2 d GS T P . . H16A H -0.347633 0.749971 0.734955 0.073 Uiso 1 2 d G U P . . H16B H -0.186380 0.759872 0.680509 0.073 Uiso 0.5 1 d G U P . . S2 S 0.0227(11) 0.6795(3) 0.3666(2) 0.0496(10) Uani 0.5 1 d G U P A -1 C2 C -0.1925(12) 0.7239(5) 0.3142(3) 0.0496(10) Uani 0.5 1 d G U P A -1 H2 H -0.306812 0.702681 0.283993 0.060 Uiso 0.5 1 calc R U P A -1 C5 C -0.172(2) 0.7949(4) 0.3234(4) 0.0496(10) Uani 0.5 1 d G U P A -1 H5A H -0.272668 0.827507 0.300027 0.060 Uiso 0.5 1 calc R U P A -1 C6 C 0.020(3) 0.8130(3) 0.3722(6) 0.0496(10) Uani 0.5 1 d G U P A -1 H6 H 0.058824 0.858778 0.384161 0.060 Uiso 0.5 1 calc R U P A -1 C8 C 0.1405(16) 0.7564(4) 0.3995(4) 0.0496(10) Uani 0.5 1 d G U P A -1 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 C4 0.019(5) 0.071(7) 0.014(4) 0.000 0.001(4) 0.000 N5 0.019(3) 0.055(4) 0.028(3) -0.007(3) 0.000(2) 0.007(3) N6 0.017(3) 0.036(3) 0.028(3) -0.003(3) -0.001(2) -0.003(3) C7 0.021(5) 0.047(6) 0.018(4) 0.000 -0.002(4) 0.000 O8 0.020(3) 0.047(4) 0.020(3) 0.000 0.004(3) 0.000 C9 0.025(4) 0.043(4) 0.045(4) -0.005(4) -0.002(3) -0.016(4) C10 0.015(3) 0.031(4) 0.042(4) -0.003(3) 0.004(3) -0.007(3) C11 0.032(4) 0.037(4) 0.034(4) -0.012(3) 0.006(3) 0.011(3) C12 0.040(4) 0.059(5) 0.033(4) -0.003(4) -0.002(4) 0.007(4) C13 0.030(4) 0.048(5) 0.059(5) 0.013(4) 0.002(4) 0.011(4) C14 0.039(5) 0.040(5) 0.108(8) -0.022(5) -0.015(5) 0.013(4) C15 0.032(4) 0.043(5) 0.085(6) -0.032(5) -0.018(5) 0.001(4) O16 0.028(4) 0.094(7) 0.023(3) 0.000 0.003(3) 0.000 S2 0.0260(14) 0.092(3) 0.0308(15) -0.025(2) -0.0041(12) 0.006(3) C2 0.0260(14) 0.092(3) 0.0308(15) -0.025(2) -0.0041(12) 0.006(3) C5 0.0260(14) 0.092(3) 0.0308(15) -0.025(2) -0.0041(12) 0.006(3) C6 0.0260(14) 0.092(3) 0.0308(15) -0.025(2) -0.0041(12) 0.006(3) C8 0.0260(14) 0.092(3) 0.0308(15) -0.025(2) -0.0041(12) 0.006(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3330 0.5570 '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 0 -12 2 0.0133 -3 -3 -3 0.0639 0 12 -2 0.0343 3 2 2 0.1466 0 3 13 0.0387 -3 -2 2 0.0695 0 -3 -13 0.0077 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 N5 C4 H4 107.6 3_565 . ? N5 C4 H4 107.6 . . ? N5 C4 N5 112.4(7) . 3_565 ? N5 C4 C8 106.6(6) 3_565 . ? N5 C4 C8 114.9(6) . . ? C8 C4 H4 107.6 . . ? C4 N5 H5 113.9 . . ? N6 N5 C4 109.3(6) . . ? N6 N5 H5 113.6 . . ? N5 N6 C9 113.5(6) . . ? C7 N6 N5 123.4(6) . . ? C7 N6 C9 123.1(6) . . ? N6 C7 N6 117.5(8) 3_565 . ? O8 C7 N6 121.2(4) . 3_565 ? O8 C7 N6 121.2(4) . . ? N6 C9 H9A 109.2 . . ? N6 C9 H9B 109.2 . . ? N6 C9 C10 112.2(6) . . ? H9A C9 H9B 107.9 . . ? C10 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C11 C10 C9 119.9(6) . . ? C15 C10 C9 121.4(7) . . ? C15 C10 C11 118.7(7) . . ? C10 C11 H11 120.0 . . ? C12 C11 C10 119.9(7) . . ? C12 C11 H11 120.0 . . ? C11 C12 H12 119.7 . . ? C13 C12 C11 120.7(7) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 120.4 . . ? C14 C13 C12 119.2(8) . . ? C14 C13 H13 120.4 . . ? C13 C14 H14 119.6 . . ? C13 C14 C15 120.9(8) . . ? C15 C14 H14 119.6 . . ? C10 C15 H15 119.7 . . ? C14 C15 C10 120.6(8) . . ? C14 C15 H15 119.7 . . ? H16A O16 H16B 109.8 . 3_565 ? H16A O16 H16B 109.8 . . ? H16B O16 H16B 25.7 . 3_565 ? C8 S2 C2 91.6 . . ? S2 C2 H2 124.6 . . ? C5 C2 S2 110.9 . . ? C5 C2 H2 124.6 . . ? C2 C5 H5A 123.6 . . ? C2 C5 C6 112.8 . . ? C6 C5 H5A 123.6 . . ? C5 C6 H6 123.6 . . ? C8 C6 C5 112.8 . . ? C8 C6 H6 123.6 . . ? C4 C8 S2 116.4(5) . . ? C6 C8 C4 131.6(5) . . ? C6 C8 S2 112.0 . . ? 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 C4 H4 0.9800 . ? C4 N5 1.456(8) 3_565 ? C4 N5 1.456(8) . ? C4 C8 1.517(11) . ? N5 H5 0.8600 . ? N5 N6 1.432(7) . ? N6 C7 1.352(7) . ? N6 C9 1.461(9) . ? C7 O8 1.236(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.513(10) . ? C10 C11 1.387(9) . ? C10 C15 1.378(10) . ? C11 H11 0.9300 . ? C11 C12 1.381(10) . ? C12 H12 0.9300 . ? C12 C13 1.372(11) . ? C13 H13 0.9300 . ? C13 C14 1.365(12) . ? C14 H14 0.9300 . ? C14 C15 1.371(12) . ? C15 H15 0.9300 . ? O16 H16A 0.8371 . ? O16 H16B 0.8499 . ? O16 H16B 0.85(10) 3_565 ? S2 C2 1.7305 . ? S2 C8 1.7196 . ? C2 H2 0.9300 . ? C2 C5 1.3739 . ? C5 H5A 0.9300 . ? C5 C6 1.4167 . ? C6 H6 0.9300 . ? C6 C8 1.3555 . ? 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 C4 N5 N6 C7 -25.9(9) . . . . ? C4 N5 N6 C9 155.9(6) . . . . ? N5 C4 N5 N6 53.6(9) 3_565 . . . ? N5 C4 C8 S2 -31.1(11) . . . . ? N5 C4 C8 S2 -156.3(7) 3_565 . . . ? N5 C4 C8 C6 151.0(5) . . . . ? N5 C4 C8 C6 25.8(9) 3_565 . . . ? N5 N6 C7 N6 -1.3(12) . . . 3_565 ? N5 N6 C7 O8 174.9(6) . . . . ? N5 N6 C9 C10 61.5(7) . . . . ? N6 C9 C10 C11 55.2(9) . . . . ? N6 C9 C10 C15 -123.4(8) . . . . ? C7 N6 C9 C10 -116.7(8) . . . . ? C9 N6 C7 N6 176.7(5) . . . 3_565 ? C9 N6 C7 O8 -7.1(12) . . . . ? C9 C10 C11 C12 179.3(7) . . . . ? C9 C10 C15 C14 -179.0(8) . . . . ? C10 C11 C12 C13 1.1(12) . . . . ? C11 C10 C15 C14 2.4(12) . . . . ? C11 C12 C13 C14 -0.4(13) . . . . ? C12 C13 C14 C15 0.7(14) . . . . ? C13 C14 C15 C10 -1.7(14) . . . . ? C15 C10 C11 C12 -2.0(11) . . . . ? S2 C2 C5 C6 0.6 . . . . ? C2 S2 C8 C4 -177.9(8) . . . . ? C2 S2 C8 C6 0.4 . . . . ? C2 C5 C6 C8 -0.3 . . . . ? C5 C6 C8 C4 177.9(10) . . . . ? C5 C6 C8 S2 -0.1 . . . . ? C8 C4 N5 N6 -68.5(8) . . . . ? C8 S2 C2 C5 -0.6 . . . . ? 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 0.1589 -12.2915 1.7850 0.8455 0.5173 0.1324 -3.0345 -3.0627 -2.6595 0.0333 0.0194 0.9993 -0.0866 12.3110 -1.7146 -0.8426 -0.5156 -0.1554 3.0934 2.4768 2.1342 0.0281 -0.0382 -0.9989 -0.0053 3.3071 12.7880 -0.5890 0.7681 -0.2513 -3.1506 -1.5491 1.5867 -0.2018 0.2647 0.9430 0.0053 -3.3071 -12.7880 0.5890 -0.7681 0.2513