#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:14 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160210.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_7160210 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 'C4 H2 N6 S2' _chemical_formula_sum 'C4 H2 N6 S2' _chemical_formula_weight 198.24 _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 2023-12-12 _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 109.377(13) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 3.7758(4) _cell_length_b 18.2803(16) _cell_length_c 5.4893(7) _cell_measurement_reflns_used 1535 _cell_measurement_temperature 98.4(8) _cell_measurement_theta_max 31.0600 _cell_measurement_theta_min 2.2220 _cell_volume 357.42(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 N~2~ _diffrn_ambient_temperature 98.4(8) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.983 _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 -25.00 5.00 0.50 2.18 -- -5.45 -95.00 -69.00 60 2 \w -15.00 12.00 0.50 2.18 -- -5.45 -99.00 30.00 54 3 \w -14.00 38.00 0.50 2.18 -- 5.68 -99.00 60.00 104 4 \w -18.00 20.00 0.50 2.18 -- 5.68 -77.00 177.00 76 5 \w -67.00 -26.00 0.50 2.18 -- 5.68 -77.00 177.00 82 ; _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 0.0837842000 _diffrn_orient_matrix_UB_12 -0.0163575000 _diffrn_orient_matrix_UB_13 0.1229950000 _diffrn_orient_matrix_UB_21 -0.1382435000 _diffrn_orient_matrix_UB_22 -0.0278999000 _diffrn_orient_matrix_UB_23 -0.0334942000 _diffrn_orient_matrix_UB_31 0.1161932000 _diffrn_orient_matrix_UB_32 -0.0213811000 _diffrn_orient_matrix_UB_33 -0.0505284000 _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 0.0244 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 2024 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.367 _diffrn_reflns_theta_min 2.228 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.26602 _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 1.842 _exptl_crystal_description block _exptl_crystal_F_000 200 _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.115 _exptl_crystal_size_min 0.061 _refine_diff_density_max 0.371 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.074 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 55 _refine_ls_number_reflns 716 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0311 _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^)+(0.0427P)^2^+0.2186P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.0793 _reflns_Friedel_coverage 0.000 _reflns_number_gt 651 _reflns_number_total 716 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01573h2.cif _cod_data_source_block exp_2588_auto _cod_database_code 7160210 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C6H7N5 _chemical_oxdiff_usercomment 98K _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 0.960 _shelx_estimated_absorpt_t_min 0.847 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C006(H006) ; _shelx_res_file ; TITL exp_2588_auto_a.res in P2(1)/n exp_2588_auto.res created by SHELXL-2018/3 at 16:51:33 on 12-Dec-2023 REM Old TITL exp_2588_auto_a.res in Pn REM SHELXT solution in P2(1)/n: R1 0.057, Rweak 0.003, Alpha 0.017 REM 0.496 for 29 systematic absences, Orientation as input REM Formula found by SHELXT: C2 N3 Cl CELL 0.71073 3.7758 18.2803 5.4893 90 109.377 90 ZERR 2 0.0004 0.0016 0.0007 0 0.013 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N S UNIT 8 4 12 4 L.S. 4 PLAN 1 SIZE 0.06 0.11 0.25 TEMP -175 BOND list 4 fmap 2 ACTA REM REM REM WGHT 0.042700 0.218600 FVAR 1.15508 S01 4 0.727714 0.594781 0.083080 11.00000 0.01750 0.01430 = 0.01206 0.00089 0.00654 0.00160 N002 3 0.658976 0.640230 0.504115 11.00000 0.01575 0.01534 = 0.01504 -0.00193 0.00501 0.00017 N003 3 0.929788 0.522543 0.558409 11.00000 0.01464 0.01500 = 0.01359 -0.00024 0.00529 0.00031 N004 3 0.549811 0.677464 0.080423 11.00000 0.01692 0.01387 = 0.01878 0.00040 0.00665 0.00047 C005 1 0.779121 0.583951 0.405315 11.00000 0.01198 0.01647 = 0.00930 -0.00076 0.00357 -0.00203 C006 1 0.535346 0.691232 0.312666 11.00000 0.01418 0.01426 = 0.01830 -0.00188 0.00473 -0.00035 AFIX 43 H006 2 0.438900 0.736644 0.346907 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_2588_auto_a.res in P2(1)/n REM wR2 = 0.0793, GooF = S = 1.085, Restrained GooF = 1.085 for all data REM R1 = 0.0311 for 651 Fo > 4sig(Fo) and 0.0352 for all 716 data REM 55 parameters refined using 0 restraints END WGHT 0.0427 0.2186 REM Highest difference peak 0.371, deepest hole -0.288, 1-sigma level 0.074 Q1 1 0.9912 0.6018 0.1392 11.00000 0.05 0.37 ; _shelx_res_checksum 95878 _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 1.805 _oxdiff_exptl_absorpt_empirical_full_min 0.375 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 S01 S 0.72771(12) 0.59478(2) 0.08308(9) 0.0142(2) Uani 1 1 d . . . . . N002 N 0.6590(4) 0.64023(9) 0.5041(3) 0.0154(4) Uani 1 1 d . . . . . N003 N 0.9298(4) 0.52254(8) 0.5584(3) 0.0143(4) Uani 1 1 d . . . . . N004 N 0.5498(5) 0.67746(8) 0.0804(3) 0.0163(4) Uani 1 1 d . . . . . C005 C 0.7791(5) 0.58395(11) 0.4053(3) 0.0126(4) Uani 1 1 d . . . . . C006 C 0.5353(5) 0.69123(10) 0.3127(4) 0.0157(4) Uani 1 1 d . . . . . H006 H 0.438900 0.736644 0.346907 0.019 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 S01 0.0175(3) 0.0143(3) 0.0121(3) 0.00089(16) 0.0065(2) 0.00160(16) N002 0.0157(8) 0.0153(8) 0.0150(9) -0.0019(6) 0.0050(6) 0.0002(6) N003 0.0146(8) 0.0150(8) 0.0136(8) -0.0002(6) 0.0053(6) 0.0003(6) N004 0.0169(8) 0.0139(8) 0.0188(9) 0.0004(6) 0.0067(7) 0.0005(6) C005 0.0120(9) 0.0165(9) 0.0093(10) -0.0008(6) 0.0036(7) -0.0020(6) C006 0.0142(9) 0.0143(9) 0.0183(11) -0.0019(7) 0.0047(7) -0.0003(7) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 -23 -3 0.0812 1 25 1 0.0332 -2 22 4 0.0297 -2 -24 0 0.0765 4 -15 -3 0.1062 1 -3 7 0.0175 -4 15 4 0.0764 -1 3 -7 0.0429 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 N004 S01 C005 91.21(9) . . ? C005 N002 C006 107.09(17) . . ? N003 N003 C005 111.9(2) 3_766 . ? C006 N004 S01 108.26(14) . . ? N002 C005 S01 113.39(14) . . ? N002 C005 N003 120.42(16) . . ? N003 C005 S01 126.19(14) . . ? N004 C006 N002 120.03(17) . . ? 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 S01 N004 1.6521(16) . ? S01 C005 1.7256(19) . ? N002 C005 1.312(2) . ? N002 C006 1.366(3) . ? N003 N003 1.264(3) 3_766 ? N003 C005 1.405(2) . ? N004 C006 1.318(3) . ? 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 1.6765 -22.9755 -3.1956 0.1232 0.5163 0.8475 1.2939 24.6009 0.6609 -0.2127 -0.8874 -0.4090 -2.1730 21.8127 3.5534 -0.1018 -0.4272 -0.8984 -2.0721 -23.5497 0.1123 0.2254 0.9397 0.2571 4.1961 -15.1286 -3.3887 0.1822 -0.0445 0.9822 0.5459 -2.8964 6.9452 0.9473 -0.2273 -0.2256 -4.1258 14.8007 3.9239 -0.1052 0.0260 -0.9941 -0.5256 2.8230 -6.9601 -0.9463 0.2270 0.2303