#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:14 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160216.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_7160216 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 _audit_creation_date 2024-02-28 _audit_creation_method ; Olex2 1.3-ac4 (compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214) ; _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 5.9619(3) _cell_length_b 8.0466(6) _cell_length_c 18.1430(11) _cell_measurement_reflns_used 3993 _cell_measurement_temperature 200.00(14) _cell_measurement_theta_max 29.9870 _cell_measurement_theta_min 2.2210 _cell_volume 870.37(9) _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 1.3-ac4 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-ac4 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 200.00(14) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.857 _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 -17.00 65.00 0.50 0.59 -- -5.45 37.00 60.00 164 2 \w 8.00 33.00 0.50 0.59 -- 5.68 71.00 64.00 50 3 \w -6.00 41.00 0.50 0.59 -- 5.68 50.00-122.00 94 4 \w -14.00 37.00 0.50 0.59 -- 5.68 -99.00 60.00 102 ; _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 -0.0951784000 _diffrn_orient_matrix_UB_12 -0.0094070000 _diffrn_orient_matrix_UB_13 0.0230870000 _diffrn_orient_matrix_UB_21 0.0010489000 _diffrn_orient_matrix_UB_22 -0.0868613000 _diffrn_orient_matrix_UB_23 -0.0064567000 _diffrn_orient_matrix_UB_31 0.0714772000 _diffrn_orient_matrix_UB_32 -0.0112059000 _diffrn_orient_matrix_UB_33 0.0308921000 _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 0.0359 _diffrn_reflns_av_unetI/netI 0.0410 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.857 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 6333 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.815 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.875 _diffrn_reflns_theta_min 2.245 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.325 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.14391 _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 1.452 _exptl_crystal_description block _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.88 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.393 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details ; Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.04(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 2249 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0463 _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^)+(0.0733P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1131 _refine_ls_wR_factor_ref 0.1183 _reflns_Friedel_coverage 0.624 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.756 _reflns_number_gt 1810 _reflns_number_total 2249 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01573h2.cif _cod_data_source_block exp_2732_auto _cod_database_code 7160216 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C7H6N4S _chemical_oxdiff_usercomment '200K, cis_Ph_NN_123N2S' _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 0.947 _shelx_estimated_absorpt_t_min 0.763 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C10(H10), C5(H5), C6(H6), C4(H4), C3(H3), C2(H2) ; _shelx_res_file ; TITL exp_2732_auto_a.res in P2(1)2(1)2(1) exp_2732_auto.res created by SHELXL-2018/3 at 12:16:55 on 28-Feb-2024 REM Old TITL exp_2732_auto in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.129, Rweak 0.023, Alpha 0.001 REM 2.256 for 19 systematic absences, Orientation as input REM Flack x = 0.003 ( 0.051 ) from 595 Parsons' quotients REM Formula found by SHELXT: C2 N11 S CELL 0.71073 5.9619 8.0466 18.143 90 90 90 ZERR 4 0.0003 0.0006 0.0011 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 1 SIZE 0.17 0.19 0.88 TEMP -73.15(14) fmap 2 ACTA OMIT 0 2 1 OMIT 1 1 0 REM REM REM WGHT 0.073300 FVAR 3.72927 S13 4 0.800615 0.357457 0.590100 11.00000 0.02749 0.04601 = 0.05814 0.01041 -0.00091 0.00010 N8 3 0.322229 0.303482 0.590515 11.00000 0.02974 0.05508 = 0.06446 0.00544 -0.00011 0.00195 N11 3 0.702052 0.622123 0.527797 11.00000 0.05453 0.04757 = 0.06215 0.01368 -0.00183 0.00051 N12 3 0.874875 0.537928 0.550510 11.00000 0.03888 0.04887 = 0.06617 0.00845 0.00534 -0.00324 N7 3 0.318258 0.174207 0.627992 11.00000 0.03147 0.05479 = 0.08923 0.01023 0.00366 0.00107 C10 1 0.505011 0.544962 0.541539 11.00000 0.03909 0.05024 = 0.05241 0.00415 -0.00600 0.00930 AFIX 43 H10 2 0.364870 0.591870 0.527820 11.00000 -1.20000 AFIX 0 C5 1 0.835343 -0.070795 0.657875 11.00000 0.05160 0.05094 = 0.05680 0.00771 0.00168 0.00794 AFIX 43 H5 2 0.924443 -0.150052 0.632401 11.00000 -1.20000 AFIX 0 C9 1 0.520761 0.396309 0.576176 11.00000 0.02799 0.04848 = 0.04469 -0.00156 -0.00120 0.00374 C1 1 0.520902 0.110650 0.661763 11.00000 0.03473 0.04481 = 0.06293 0.01290 0.00502 -0.00501 C6 1 0.644981 -0.007042 0.625164 11.00000 0.04521 0.05131 = 0.05120 0.00529 0.00153 -0.00101 AFIX 43 H6 2 0.600128 -0.044271 0.577710 11.00000 -1.20000 AFIX 0 C4 1 0.896813 -0.018874 0.728278 11.00000 0.04853 0.05824 = 0.06293 0.01565 -0.00827 -0.00632 AFIX 43 H4 2 1.030091 -0.060529 0.750241 11.00000 -1.20000 AFIX 0 C3 1 0.764042 0.093363 0.766340 11.00000 0.06210 0.05314 = 0.05313 0.00251 0.00116 -0.01217 AFIX 43 H3 2 0.802772 0.125407 0.815102 11.00000 -1.20000 AFIX 0 C2 1 0.576217 0.158078 0.733265 11.00000 0.05257 0.05145 = 0.06792 -0.00198 0.01299 -0.00159 AFIX 43 H2 2 0.484329 0.234965 0.759096 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_2732_auto_a.res in P2(1)2(1)2(1) REM wR2 = 0.1183, GooF = S = 1.030, Restrained GooF = 1.030 for all data REM R1 = 0.0463 for 1810 Fo > 4sig(Fo) and 0.0590 for all 2249 data REM 118 parameters refined using 0 restraints END WGHT 0.0734 0.0000 REM Highest difference peak 0.393, deepest hole -0.185, 1-sigma level 0.073 Q1 1 0.8414 0.4738 0.5896 11.00000 0.05 0.39 ; _shelx_res_checksum 69071 _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 2.881 _oxdiff_exptl_absorpt_empirical_full_min 0.248 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 0.80062(12) 0.35746(10) 0.59010(4) 0.0439(2) Uani 1 1 d . . . . . N8 N 0.3222(4) 0.3035(4) 0.59051(15) 0.0498(6) Uani 1 1 d . . . . . N11 N 0.7021(5) 0.6221(4) 0.52780(16) 0.0548(7) Uani 1 1 d . . . . . N12 N 0.8749(5) 0.5379(4) 0.55051(17) 0.0513(7) Uani 1 1 d . . . . . N7 N 0.3183(5) 0.1742(4) 0.62799(18) 0.0585(8) Uani 1 1 d . . . . . C10 C 0.5050(6) 0.5450(4) 0.54154(18) 0.0472(8) Uani 1 1 d . . . . . H10 H 0.364870 0.591870 0.527820 0.057 Uiso 1 1 calc R U . . . C5 C 0.8353(6) -0.0708(5) 0.65787(18) 0.0531(8) Uani 1 1 d . . . . . H5 H 0.924443 -0.150052 0.632401 0.064 Uiso 1 1 calc R U . . . C9 C 0.5208(5) 0.3963(4) 0.57618(16) 0.0404(7) Uani 1 1 d . . . . . C1 C 0.5209(5) 0.1107(4) 0.66176(19) 0.0475(8) Uani 1 1 d . . . . . C6 C 0.6450(6) -0.0070(5) 0.62516(17) 0.0492(8) Uani 1 1 d . . . . . H6 H 0.600128 -0.044271 0.577710 0.059 Uiso 1 1 calc R U . . . C4 C 0.8968(7) -0.0189(5) 0.7283(2) 0.0566(9) Uani 1 1 d . . . . . H4 H 1.030091 -0.060529 0.750241 0.068 Uiso 1 1 calc R U . . . C3 C 0.7640(7) 0.0934(5) 0.7663(2) 0.0561(9) Uani 1 1 d . . . . . H3 H 0.802772 0.125407 0.815102 0.067 Uiso 1 1 calc R U . . . C2 C 0.5762(6) 0.1581(5) 0.7333(2) 0.0573(9) Uani 1 1 d . . . . . H2 H 0.484329 0.234965 0.759096 0.069 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 0.0275(3) 0.0460(4) 0.0581(4) 0.0104(3) -0.0009(3) 0.0001(3) N8 0.0297(13) 0.0551(16) 0.0645(15) 0.0054(14) -0.0001(13) 0.0020(12) N11 0.0545(16) 0.0476(15) 0.0622(15) 0.0137(13) -0.0018(14) 0.0005(16) N12 0.0389(14) 0.0489(18) 0.0662(16) 0.0085(14) 0.0053(13) -0.0032(13) N7 0.0315(13) 0.0548(18) 0.089(2) 0.0102(15) 0.0037(13) 0.0011(14) C10 0.0391(16) 0.0502(19) 0.0524(17) 0.0042(14) -0.0060(13) 0.0093(15) C5 0.052(2) 0.0509(18) 0.0568(17) 0.0077(16) 0.0017(16) 0.0079(16) C9 0.0280(13) 0.0485(18) 0.0447(14) -0.0016(13) -0.0012(10) 0.0037(12) C1 0.0347(15) 0.0448(18) 0.0629(19) 0.0129(15) 0.0050(14) -0.0050(14) C6 0.0452(19) 0.0513(19) 0.0512(17) 0.0053(15) 0.0015(13) -0.0010(15) C4 0.0485(19) 0.058(2) 0.0629(19) 0.0156(19) -0.0083(16) -0.0063(17) C3 0.062(2) 0.0531(19) 0.0531(16) 0.0025(15) 0.0012(16) -0.0122(18) C2 0.053(2) 0.051(2) 0.068(2) -0.0020(19) 0.0130(16) -0.0016(18) 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 N12 S13 C9 92.05(16) . . ? N7 N8 C9 123.7(3) . . ? N12 N11 C10 113.0(3) . . ? N11 N12 S13 112.2(2) . . ? N8 N7 C1 120.7(3) . . ? N11 C10 C9 115.5(3) . . ? C6 C5 C4 120.0(4) . . ? N8 C9 S13 133.3(2) . . ? C10 C9 S13 107.3(2) . . ? C10 C9 N8 119.4(3) . . ? C6 C1 N7 119.2(3) . . ? C6 C1 C2 120.8(3) . . ? C2 C1 N7 119.7(3) . . ? C1 C6 C5 119.5(3) . . ? C3 C4 C5 120.2(4) . . ? C2 C3 C4 119.7(3) . . ? C3 C2 C1 119.8(3) . . ? 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 N12 1.680(3) . ? S13 C9 1.716(3) . ? N8 N7 1.243(4) . ? N8 C9 1.424(4) . ? N11 N12 1.300(4) . ? N11 C10 1.352(5) . ? N7 C1 1.448(4) . ? C10 C9 1.354(5) . ? C5 C6 1.380(5) . ? C5 C4 1.393(5) . ? C1 C6 1.373(5) . ? C1 C2 1.392(5) . ? C4 C3 1.385(6) . ? C3 C2 1.373(6) . ?