#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:14 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160212.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_7160212 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 H8 N4 S2' _chemical_formula_sum 'C8 H8 N4 S2' _chemical_formula_weight 224.30 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-06-13 _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 118.281(9) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.3127(8) _cell_length_b 5.0803(2) _cell_length_c 10.6479(7) _cell_measurement_reflns_used 1537 _cell_measurement_temperature 292.95(10) _cell_measurement_theta_max 28.1710 _cell_measurement_theta_min 2.2560 _cell_volume 491.27(7) _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 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment air _diffrn_ambient_temperature 292.95(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 0.864 _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 -8.00 92.00 0.50 0.11 -- 20.67 61.00-106.00 200 2 \w 1.00 28.00 0.50 0.11 -- -20.52 -99.00-120.00 54 3 \w 9.00 35.00 0.50 0.11 -- -20.52 -99.00 -60.00 52 4 \w -18.00 35.00 0.50 0.11 -- -20.52 -99.00 -30.00 106 5 \w -48.00 36.00 0.50 0.11 -- 20.67 -61.00 114.00 168 6 \w 58.00 91.00 0.50 0.05 -- 20.83 178.00-180.00 66 7 \w -66.00 -41.00 0.50 0.05 -- -20.67 -61.00 114.00 50 ; _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 -0.0467787000 _diffrn_orient_matrix_UB_12 0.0999940000 _diffrn_orient_matrix_UB_13 -0.0453779000 _diffrn_orient_matrix_UB_21 -0.0365177000 _diffrn_orient_matrix_UB_22 0.0072834000 _diffrn_orient_matrix_UB_23 0.0419899000 _diffrn_orient_matrix_UB_31 0.0509111000 _diffrn_orient_matrix_UB_32 0.0971473000 _diffrn_orient_matrix_UB_33 0.0436016000 _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 0.0290 _diffrn_reflns_av_unetI/netI 0.0369 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.864 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3086 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.864 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.820 _diffrn_reflns_theta_min 2.265 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.505 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.69775 _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 1.516 _exptl_crystal_description prism _exptl_crystal_F_000 232 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.215 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 65 _refine_ls_number_reflns 1107 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0366 _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^)+(0.0543P)^2^+0.0883P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0937 _refine_ls_wR_factor_ref 0.1021 _reflns_Friedel_coverage 0.000 _reflns_number_gt 931 _reflns_number_total 1107 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01573h2.cif _cod_data_source_block exp_2887_auto _cod_original_cell_volume 491.27(6) _cod_database_code 7160212 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula CHNO _chemical_oxdiff_usercomment 293K _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 0.966 _shelx_estimated_absorpt_t_min 0.847 _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: C4(H4) 2.b Idealised Me refined as rotating group: C7(H7A,H7B,H7C) ; _shelx_res_file ; TITL exp_2887_auto_a.res in P2(1)/n exp_2887_auto.res created by SHELXL-2018/3 at 18:01:04 on 13-Jun-2024 REM Old TITL exp_2887_auto in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.114, Rweak 0.301, Alpha 0.017 REM 0.229 for 118 systematic absences, Orientation as input REM Formula found by SHELXT: C7 N5 Cl CELL 0.71073 10.3127 5.0803 10.6479 90 118.281 90 ZERR 2 0.0008 0.0002 0.0007 0 0.009 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N S UNIT 16 16 8 4 L.S. 4 PLAN 5 SIZE 0.07 0.29 0.34 TEMP 19.8(1) HTAB fmap 2 acta REM REM REM WGHT 0.054300 0.088300 FVAR 1.34998 S2 4 0.398557 0.388065 0.294913 11.00000 0.03729 0.03797 = 0.04014 0.00600 0.02183 0.00347 N6 3 0.559682 0.010176 0.496652 11.00000 0.03625 0.03484 = 0.03477 0.00174 0.01973 0.00029 N5 3 0.666736 0.240767 0.378588 11.00000 0.03849 0.04658 = 0.04992 0.00965 0.02646 0.00314 C1 1 0.552953 0.199006 0.398956 11.00000 0.03455 0.03377 = 0.03071 -0.00033 0.01738 0.00047 C3 1 0.494322 0.533147 0.218225 11.00000 0.04530 0.03225 = 0.03378 -0.00144 0.02242 -0.00623 C4 1 0.632638 0.428925 0.276146 11.00000 0.04560 0.04416 = 0.05029 0.00624 0.03178 -0.00240 AFIX 43 H4 2 0.700454 0.483467 0.247218 11.00000 -1.20000 AFIX 0 C7 1 0.428438 0.737548 0.103409 11.00000 0.05777 0.03951 = 0.04104 0.00665 0.02177 -0.00362 AFIX 137 H7A 2 0.343609 0.665726 0.023015 11.00000 -1.50000 H7B 2 0.499825 0.790049 0.074573 11.00000 -1.50000 H7C 2 0.399690 0.887759 0.139115 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_2887_auto_a.res in P2(1)/n REM wR2 = 0.1021, GooF = S = 1.049, Restrained GooF = 1.049 for all data REM R1 = 0.0366 for 931 Fo > 4sig(Fo) and 0.0448 for all 1107 data REM 65 parameters refined using 0 restraints END WGHT 0.0543 0.0883 REM Instructions for potential hydrogen bonds EQIV $2 -x+3/2, y+1/2, -z+1/2 HTAB C4 N5_$2 REM Highest difference peak 0.215, deepest hole -0.276, 1-sigma level 0.062 Q1 1 0.4959 0.3304 0.3834 11.00000 0.05 0.22 Q2 1 0.4265 0.4123 0.2159 11.00000 0.05 0.21 Q3 1 0.3245 0.8490 0.0742 11.00000 0.05 0.20 Q4 1 0.2785 0.3691 0.1862 11.00000 0.05 0.19 Q5 1 0.4926 0.5887 0.0284 11.00000 0.05 0.19 ; _shelx_res_checksum 94141 _olex2_exptl_crystal_mounting_method 'MiTeGen Micromount' _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 2.031 _oxdiff_exptl_absorpt_empirical_full_min 0.511 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 S2 S 0.39856(6) 0.38806(9) 0.29491(5) 0.0370(2) Uani 1 1 d . . . . . N6 N 0.55968(17) 0.0102(3) 0.49665(16) 0.0341(4) Uani 1 1 d . . . . . N5 N 0.66674(19) 0.2408(3) 0.37859(19) 0.0428(4) Uani 1 1 d . . . . . C1 C 0.5530(2) 0.1990(4) 0.39896(18) 0.0322(4) Uani 1 1 d . . . . . C3 C 0.4943(2) 0.5331(4) 0.21822(19) 0.0356(5) Uani 1 1 d . . . . . C4 C 0.6326(3) 0.4289(4) 0.2761(2) 0.0430(5) Uani 1 1 d . . . . . H4 H 0.700454 0.483467 0.247218 0.052 Uiso 1 1 calc R U . . . C7 C 0.4284(3) 0.7375(4) 0.1034(2) 0.0468(5) Uani 1 1 d . . . . . H7A H 0.343609 0.665726 0.023015 0.070 Uiso 1 1 calc R U . . . H7B H 0.499825 0.790049 0.074573 0.070 Uiso 1 1 calc R U . . . H7C H 0.399690 0.887759 0.139115 0.070 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 S2 0.0373(4) 0.0380(3) 0.0401(3) 0.00600(18) 0.0218(3) 0.00347(18) N6 0.0363(10) 0.0348(8) 0.0348(8) 0.0017(6) 0.0197(7) 0.0003(7) N5 0.0385(11) 0.0466(10) 0.0499(10) 0.0097(8) 0.0265(9) 0.0031(7) C1 0.0346(11) 0.0338(9) 0.0307(9) -0.0003(7) 0.0174(8) 0.0005(7) C3 0.0453(12) 0.0323(10) 0.0338(9) -0.0014(7) 0.0224(9) -0.0062(8) C4 0.0456(13) 0.0442(11) 0.0503(12) 0.0062(9) 0.0318(11) -0.0024(9) C7 0.0578(15) 0.0395(11) 0.0410(11) 0.0066(8) 0.0218(11) -0.0036(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 C3 S2 C1 88.89(9) . . ? N6 N6 C1 113.04(19) 3_656 . ? C1 N5 C4 109.54(18) . . ? N6 C1 S2 124.33(15) . . ? N5 C1 S2 115.35(14) . . ? N5 C1 N6 120.31(17) . . ? C4 C3 S2 109.39(15) . . ? C4 C3 C7 127.61(19) . . ? C7 C3 S2 122.99(17) . . ? C3 C4 N5 116.82(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 S2 C1 1.7360(19) . ? S2 C3 1.717(2) . ? N6 N6 1.270(3) 3_656 ? N6 C1 1.392(2) . ? N5 C1 1.308(2) . ? N5 C4 1.365(3) . ? C3 C4 1.364(3) . ? C3 C7 1.499(3) . ?