#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:14 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160215.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_7160215 loop_ _publ_author_name 'Cheruthu, Nusaiba Madappuram' 'Hashim, P. K.' 'Sahu, Saugata' 'Takahashi, Kiyonori' 'Nakamura, Takayoshi' 'Mitomo, Hideyuki' 'Ijiro, Kuniharu' 'Tamaoki, Nobuyuki' _publ_section_title ; Azophotoswitches containing thiazole, isothiazole, thiadiazole, and isothiadiazole ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01573H _journal_year 2024 _chemical_formula_moiety 'C8 H6 N4 S' _chemical_formula_sum 'C8 H6 N4 S' _chemical_formula_weight 190.23 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-03-07 _audit_creation_method ; Olex2 1.5-ac5-023 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2024-07-16 deposited with the CCDC. 2024-11-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.6262(2) _cell_length_b 10.7086(4) _cell_length_c 17.0055(7) _cell_measurement_reflns_used 6979 _cell_measurement_temperature 199.90(14) _cell_measurement_theta_max 30.6840 _cell_measurement_theta_min 2.2600 _cell_volume 842.45(6) _computing_cell_refinement 'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 199.90(14) _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 0.880 _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 -18.00 38.00 0.50 1.79 -- 5.68 -99.00 -60.00 112 2 \w -18.00 38.00 0.50 1.79 -- 5.68 -99.00 0.00 112 3 \w -67.00 -8.00 0.50 1.79 -- 5.68 -37.00 90.00 118 4 \w -7.00 78.00 0.50 1.79 -- 5.68 40.00 68.00 170 5 \w -22.00 40.00 0.50 1.79 -- 5.68 89.00-168.00 124 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0768119000 _diffrn_orient_matrix_UB_12 -0.0412923000 _diffrn_orient_matrix_UB_13 0.0250480000 _diffrn_orient_matrix_UB_21 -0.0115930000 _diffrn_orient_matrix_UB_22 0.0436876000 _diffrn_orient_matrix_UB_23 0.0311885000 _diffrn_orient_matrix_UB_31 -0.1321504000 _diffrn_orient_matrix_UB_32 -0.0278476000 _diffrn_orient_matrix_UB_33 0.0118136000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_unetI/netI 0.0322 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.880 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 9703 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.845 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.786 _diffrn_reflns_theta_min 2.248 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.39162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.500 _exptl_crystal_description block _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.281 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details ; Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 2235 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0291 _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^)+(0.0392P)^2^+0.0205P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.0705 _reflns_Friedel_coverage 0.623 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.794 _reflns_number_gt 1988 _reflns_number_total 2235 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01573h2.cif _cod_data_source_block exp_2755_auto _cod_database_code 7160215 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C8H6N4S _chemical_oxdiff_usercomment 200K _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C6(H6), C5(H5), C3(H3), C12(H12), C4(H4) ; _shelx_res_file ; TITL exp_2755_auto_a.res in P2(1)2(1)2(1) exp_2755_auto.res created by SHELXL-2018/3 at 11:57:12 on 07-Mar-2024 REM Old TITL exp_2755_auto in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.072, Rweak 0.013, Alpha 0.001 REM 0.511 for 19 systematic absences, Orientation as input REM Flack x = 0.027 ( 0.036 ) from 626 Parsons' quotients REM Formula found by SHELXT: C4 N7 S CELL 0.71073 4.6262 10.7086 17.0055 90 90 90 ZERR 4 0.0002 0.0004 0.0007 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N S UNIT 32 24 16 4 L.S. 4 PLAN 5 TEMP -73 fmap 2 ACTA REM REM REM WGHT 0.039200 0.020500 FVAR 2.07007 S13 4 0.119113 0.770370 0.696419 11.00000 0.03385 0.02534 = 0.03371 0.00006 0.00380 0.00181 N8 3 0.392311 0.544090 0.664670 11.00000 0.02714 0.02478 = 0.02629 -0.00038 -0.00030 -0.00087 N7 3 0.505466 0.608442 0.610962 11.00000 0.02424 0.02469 = 0.02648 -0.00066 -0.00180 -0.00184 N10 3 0.051197 0.559193 0.765873 11.00000 0.03923 0.03059 = 0.03272 0.00028 0.00700 -0.00084 N11 3 -0.133269 0.641685 0.803252 11.00000 0.03834 0.03898 = 0.03354 -0.00423 0.01002 -0.00181 C1 1 0.710207 0.543189 0.564267 11.00000 0.02291 0.02426 = 0.02545 -0.00149 -0.00254 -0.00152 C2 1 0.803533 0.421525 0.578648 11.00000 0.02942 0.02343 = 0.02921 0.00172 0.00051 -0.00242 AFIX 43 H2 2 0.726175 0.375350 0.621455 11.00000 -1.20000 AFIX 0 C9 1 0.194492 0.613479 0.709592 11.00000 0.02666 0.02365 = 0.02565 -0.00205 -0.00153 -0.00185 C6 1 0.819623 0.609926 0.500670 11.00000 0.03123 0.02536 = 0.03094 0.00548 -0.00058 0.00080 AFIX 43 H6 2 0.755822 0.692816 0.490921 11.00000 -1.20000 AFIX 0 C5 1 1.022032 0.554898 0.451650 11.00000 0.03421 0.04011 = 0.03013 0.00666 0.00396 -0.00094 AFIX 43 H5 2 1.096175 0.600015 0.407983 11.00000 -1.20000 AFIX 0 C3 1 1.009071 0.368767 0.530217 11.00000 0.03266 0.02487 = 0.03796 -0.00219 -0.00259 0.00139 AFIX 43 H3 2 1.077757 0.286862 0.540777 11.00000 -1.20000 AFIX 0 C12 1 -0.118183 0.753018 0.772622 11.00000 0.02994 0.03550 = 0.03186 -0.00885 0.00067 -0.00012 AFIX 43 H12 2 -0.232181 0.820435 0.791509 11.00000 -1.20000 AFIX 0 C4 1 1.116607 0.434495 0.466042 11.00000 0.03039 0.03754 = 0.02934 -0.00624 0.00043 0.00314 AFIX 43 H4 2 1.254662 0.396810 0.432172 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_2755_auto_a.res in P2(1)2(1)2(1) REM wR2 = 0.0705, GooF = S = 1.047, Restrained GooF = 1.047 for all data REM R1 = 0.0291 for 1988 Fo > 4sig(Fo) and 0.0357 for all 2235 data REM 118 parameters refined using 0 restraints END WGHT 0.0392 0.0205 REM Highest difference peak 0.281, deepest hole -0.159, 1-sigma level 0.042 Q1 1 0.1289 0.6903 0.6992 11.00000 0.05 0.28 Q2 1 0.7424 0.5603 0.5240 11.00000 0.05 0.19 Q3 1 0.0708 0.4835 0.7649 11.00000 0.05 0.18 Q4 1 0.8617 0.5592 0.4751 11.00000 0.05 0.16 Q5 1 -0.0812 0.6998 0.7992 11.00000 0.05 0.16 ; _shelx_res_checksum 54226 _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 1.923 _oxdiff_exptl_absorpt_empirical_full_min 0.413 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S13 S 0.11911(10) 0.77037(4) 0.69642(3) 0.03097(14) Uani 1 1 d . . . . . N8 N 0.3923(3) 0.54409(13) 0.66467(9) 0.0261(3) Uani 1 1 d . . . . . N7 N 0.5055(3) 0.60844(14) 0.61096(9) 0.0251(3) Uani 1 1 d . . . . . N10 N 0.0512(4) 0.55919(15) 0.76587(10) 0.0342(4) Uani 1 1 d . . . . . N11 N -0.1333(4) 0.64169(15) 0.80325(10) 0.0370(4) Uani 1 1 d . . . . . C1 C 0.7102(4) 0.54319(16) 0.56427(11) 0.0242(4) Uani 1 1 d . . . . . C2 C 0.8035(4) 0.42152(16) 0.57865(11) 0.0274(4) Uani 1 1 d . . . . . H2 H 0.726175 0.375350 0.621455 0.033 Uiso 1 1 calc R U . . . C9 C 0.1945(4) 0.61348(15) 0.70959(10) 0.0253(4) Uani 1 1 d . . . . . C6 C 0.8196(4) 0.60993(16) 0.50067(11) 0.0292(4) Uani 1 1 d . . . . . H6 H 0.755822 0.692816 0.490921 0.035 Uiso 1 1 calc R U . . . C5 C 1.0220(4) 0.5549(2) 0.45165(12) 0.0348(4) Uani 1 1 d . . . . . H5 H 1.096175 0.600015 0.407983 0.042 Uiso 1 1 calc R U . . . C3 C 1.0091(4) 0.36877(17) 0.53022(12) 0.0318(4) Uani 1 1 d . . . . . H3 H 1.077757 0.286862 0.540777 0.038 Uiso 1 1 calc R U . . . C12 C -0.1182(4) 0.75302(18) 0.77262(12) 0.0324(4) Uani 1 1 d . . . . . H12 H -0.232181 0.820435 0.791509 0.039 Uiso 1 1 calc R U . . . C4 C 1.1166(5) 0.43450(17) 0.46604(11) 0.0324(4) Uani 1 1 d . . . . . H4 H 1.254662 0.396810 0.432172 0.039 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 S13 0.0338(2) 0.0253(2) 0.0337(3) 0.00006(17) 0.0038(2) 0.00181(17) N8 0.0271(7) 0.0248(7) 0.0263(7) -0.0004(6) -0.0003(7) -0.0009(7) N7 0.0242(7) 0.0247(7) 0.0265(8) -0.0007(6) -0.0018(6) -0.0018(6) N10 0.0392(10) 0.0306(8) 0.0327(9) 0.0003(7) 0.0070(7) -0.0008(7) N11 0.0383(9) 0.0390(8) 0.0335(9) -0.0042(7) 0.0100(9) -0.0018(7) C1 0.0229(8) 0.0243(8) 0.0254(9) -0.0015(7) -0.0025(7) -0.0015(6) C2 0.0294(10) 0.0234(8) 0.0292(10) 0.0017(7) 0.0005(7) -0.0024(7) C9 0.0267(9) 0.0237(8) 0.0256(9) -0.0020(7) -0.0015(7) -0.0018(6) C6 0.0312(10) 0.0254(8) 0.0309(10) 0.0055(8) -0.0006(7) 0.0008(7) C5 0.0342(10) 0.0401(10) 0.0301(10) 0.0067(8) 0.0040(8) -0.0009(8) C3 0.0327(9) 0.0249(9) 0.0380(11) -0.0022(8) -0.0026(9) 0.0014(7) C12 0.0299(9) 0.0355(10) 0.0319(9) -0.0089(7) 0.0007(8) -0.0001(8) C4 0.0304(9) 0.0375(10) 0.0293(9) -0.0062(7) 0.0004(9) 0.0031(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 S13 C9 85.74(9) . . ? N7 N8 C9 112.09(14) . . ? N8 N7 C1 114.45(15) . . ? C9 N10 N11 111.53(16) . . ? C12 N11 N10 111.57(16) . . ? C2 C1 N7 124.64(16) . . ? C6 C1 N7 115.12(15) . . ? C6 C1 C2 120.24(17) . . ? C3 C2 C1 119.45(17) . . ? N8 C9 S13 125.06(13) . . ? N10 C9 S13 115.23(14) . . ? N10 C9 N8 119.71(16) . . ? C5 C6 C1 119.67(17) . . ? C4 C5 C6 120.25(18) . . ? C2 C3 C4 120.53(18) . . ? N11 C12 S13 115.92(15) . . ? C5 C4 C3 119.83(19) . . ? 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 S13 C9 1.7304(17) . ? S13 C12 1.708(2) . ? N8 N7 1.258(2) . ? N8 C9 1.405(2) . ? N7 C1 1.420(2) . ? N10 N11 1.383(2) . ? N10 C9 1.301(2) . ? N11 C12 1.303(3) . ? C1 C2 1.394(3) . ? C1 C6 1.392(2) . ? C2 C3 1.379(3) . ? C6 C5 1.385(3) . ? C5 C4 1.383(3) . ? C3 C4 1.391(3) . ?