#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:14 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160211.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_7160211 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 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-12-12 _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 95.154(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.4717(3) _cell_length_b 9.3558(5) _cell_length_c 7.3148(4) _cell_measurement_reflns_used 2786 _cell_measurement_temperature 98.8(6) _cell_measurement_theta_max 31.0690 _cell_measurement_theta_min 3.5250 _cell_volume 372.95(4) _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)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 98.8(6) _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 1.000 _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 -7.00 64.00 0.50 0.24 -- 5.68 35.00 30.00 142 2 \w -32.00 15.00 0.50 0.24 -- 5.68 -35.00-126.00 94 3 \w -66.00 -40.00 0.50 0.24 -- 5.68 -37.00-180.00 52 4 \w -19.00 18.00 0.50 0.24 -- 5.68 -37.00-180.00 74 5 \w -14.00 36.00 0.50 0.24 -- 5.68 -99.00-180.00 100 6 \w -61.00 -35.00 0.50 0.05 -- -5.53 -35.00-126.00 52 7 \w 1.00 48.00 0.50 0.05 -- -5.53 35.00 30.00 94 8 \w -10.00 24.00 0.50 0.05 -- -5.53 -99.00 -90.00 68 9 \w -18.00 7.00 0.50 0.05 -- -5.53 -99.00-120.00 50 10 \w -6.00 26.00 0.50 0.05 -- -5.53 -99.00 150.00 64 11 \w 52.00 79.00 0.50 0.05 -- 5.84 37.00 150.00 54 12 \w 0.00 47.00 0.50 0.05 -- 5.84 37.00 150.00 94 ; _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 0.0972462000 _diffrn_orient_matrix_UB_12 0.0227044000 _diffrn_orient_matrix_UB_13 0.0641433000 _diffrn_orient_matrix_UB_21 -0.0657011000 _diffrn_orient_matrix_UB_22 -0.0248910000 _diffrn_orient_matrix_UB_23 0.0729515000 _diffrn_orient_matrix_UB_31 0.0565317000 _diffrn_orient_matrix_UB_32 -0.0679188000 _diffrn_orient_matrix_UB_33 -0.0052798000 _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 0.0578 _diffrn_reflns_av_unetI/netI 0.0302 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 5465 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.362 _diffrn_reflns_theta_min 3.544 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.659 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93672 _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 1.765 _exptl_crystal_description block _exptl_crystal_F_000 200 _exptl_crystal_size_max 0.168 _exptl_crystal_size_mid 0.106 _exptl_crystal_size_min 0.075 _refine_diff_density_max 0.170 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 756 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0218 _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^)+(0.0295P)^2^+0.0164P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.0569 _reflns_Friedel_coverage 0.000 _reflns_number_gt 683 _reflns_number_total 756 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01573h2.cif _cod_data_source_block exp_2589_auto _cod_database_code 7160211 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C4H2N8S2 _chemical_oxdiff_usercomment 99K _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 100.00 _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. Rigid bond restraints C1, S002 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005 3. Others Sof(S002)=Sof(C0)=Sof(H0)=Sof(C1)=Sof(N1)=1-FVAR(1) Sof(S001)=Sof(N005)=Sof(C006)=Sof(C2)=Sof(H2)=FVAR(1) 4.a Aromatic/amide H refined with riding coordinates: C0(H0), C2(H2) ; _shelx_res_file ; TITL exp_2589_auto_a.res in P2(1)/c exp_2589_auto.res created by SHELXL-2018/3 at 16:42:55 on 12-Dec-2023 REM Old TITL exp_2589_auto_a.res in P2(1) REM SHELXT solution in P2(1)/c: R1 0.177, Rweak 0.010, Alpha 0.042 REM 0.177 for 54 systematic absences, Orientation as input REM Formula found by SHELXT: N2 S CELL 0.71073 5.4717 9.3558 7.3148 90 95.154 90 ZERR 2 0.0003 0.0005 0.0004 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N S UNIT 8 4 12 4 DELU 0.005 0.005 C1 S002 L.S. 4 PLAN 2 TEMP -174 BOND list 4 fmap 2 ACTA REM REM REM WGHT 0.029500 0.016400 FVAR 0.76341 0.57532 PART 1 S001 4 0.502491 0.204452 0.527326 21.00000 0.02157 0.01594 = 0.02398 -0.00181 0.00429 -0.00153 PART 2 S002 4 0.906318 0.341250 0.656368 -21.00000 0.01662 0.02384 = 0.02525 -0.00061 0.00086 -0.00316 PART 0 N003 3 0.727310 0.097792 0.618233 11.00000 0.02941 0.02037 = 0.02680 0.00275 0.00510 0.00379 N004 3 0.924272 0.166850 0.679739 11.00000 0.02704 0.02524 = 0.02789 0.00409 0.00383 0.00423 PART 1 N005 3 0.608143 0.494703 0.539138 21.00000 0.01983 0.01687 = 0.01840 0.00138 0.00311 0.00105 C006 1 0.679008 0.353009 0.579592 21.00000 0.01019 0.01789 = 0.01665 -0.00237 -0.00160 -0.00235 PART 2 C0 1 0.541502 0.191419 0.553384 -21.00000 0.04853 0.04655 = 0.03323 -0.01567 0.00947 -0.02518 AFIX 43 H0 2 0.382155 0.159456 0.509468 -21.00000 -1.20000 AFIX 0 PART 1 C2 1 0.887205 0.313170 0.655979 21.00000 0.02675 0.05211 = 0.03497 -0.00850 0.00680 -0.01746 AFIX 43 H2 2 1.011189 0.380444 0.694827 21.00000 -1.20000 AFIX 0 PART 2 C1 1 0.604135 0.330021 0.557511 -21.00000 0.00523 0.02622 = 0.01191 -0.00208 -0.00425 0.00032 N1 3 0.447172 0.440459 0.496286 -21.00000 0.02089 0.02215 = 0.01980 -0.00008 0.00317 -0.00356 HKLF 4 REM exp_2589_auto_a.res in P2(1)/c REM wR2 = 0.0569, GooF = S = 1.052, Restrained GooF = 1.056 for all data REM R1 = 0.0218 for 683 Fo > 4sig(Fo) and 0.0257 for all 756 data REM 92 parameters refined using 1 restraints END WGHT 0.0295 0.0164 REM Highest difference peak 0.170, deepest hole -0.186, 1-sigma level 0.042 Q1 1 1.0905 0.3577 0.7152 11.00000 0.05 0.17 Q2 1 1.0759 0.1212 0.6557 11.00000 0.05 0.14 ; _shelx_res_checksum 46502 _olex2_exptl_crystal_mounting_method Cryoloop _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 1.341 _oxdiff_exptl_absorpt_empirical_full_min 0.803 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 S001 S 0.5025(5) 0.2045(2) 0.5273(3) 0.0204(3) Uani 0.575(2) 1 d . . P A 1 S002 S 0.9063(6) 0.3412(5) 0.6564(4) 0.0220(4) Uani 0.425(2) 1 d . U P A 2 N003 N 0.7273(2) 0.09779(10) 0.61823(13) 0.0254(3) Uani 1 1 d . . . . . N004 N 0.92427(19) 0.16685(10) 0.67974(14) 0.0266(3) Uani 1 1 d . . . . . N005 N 0.6081(4) 0.4947(3) 0.5391(3) 0.0183(5) Uani 0.575(2) 1 d . . P A 1 C006 C 0.6790(7) 0.3530(6) 0.5796(7) 0.0151(8) Uani 0.575(2) 1 d . . P A 1 C0 C 0.542(3) 0.1914(16) 0.5534(17) 0.042(4) Uani 0.425(2) 1 d . . P A 2 H0 H 0.382155 0.159456 0.509468 0.051 Uiso 0.425(2) 1 calc R U P A 2 C2 C 0.887(2) 0.3132(10) 0.6560(15) 0.038(4) Uani 0.575(2) 1 d . . P A 1 H2 H 1.011189 0.380444 0.694827 0.045 Uiso 0.575(2) 1 calc R U P A 1 C1 C 0.6041(11) 0.3300(8) 0.5575(9) 0.0148(11) Uani 0.425(2) 1 d . U P A 2 N1 N 0.4472(7) 0.4405(4) 0.4963(4) 0.0209(7) Uani 0.425(2) 1 d . . P A 2 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 S001 0.0216(5) 0.0159(4) 0.0240(5) -0.0018(3) 0.0043(5) -0.0015(3) S002 0.0166(8) 0.0238(8) 0.0253(7) -0.0006(4) 0.0009(5) -0.0032(8) N003 0.0294(6) 0.0204(5) 0.0268(6) 0.0028(4) 0.0051(5) 0.0038(4) N004 0.0270(6) 0.0252(6) 0.0279(6) 0.0041(4) 0.0038(5) 0.0042(4) N005 0.0198(14) 0.0169(12) 0.0184(9) 0.0014(8) 0.0031(8) 0.0010(9) C006 0.010(2) 0.0179(15) 0.0166(17) -0.0024(11) -0.0016(16) -0.0024(16) C0 0.049(8) 0.047(7) 0.033(5) -0.016(4) 0.009(4) -0.025(5) C2 0.027(3) 0.052(7) 0.035(3) -0.008(3) 0.0068(18) -0.017(3) C1 0.005(3) 0.026(3) 0.0119(19) -0.0021(15) -0.0043(19) 0.0003(19) N1 0.0209(18) 0.0222(17) 0.0198(13) -0.0001(11) 0.0032(11) -0.0036(17) 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 N003 S001 C006 90.9(2) . . ? N004 S002 C1 91.7(3) . . ? N004 N003 S001 113.41(12) . . ? N004 N003 C0 111.2(7) . . ? N003 N004 S002 114.66(16) . . ? N003 N004 C2 109.8(5) . . ? N005 N005 C006 113.4(4) 3_666 . ? N005 C006 S001 125.3(3) . . ? C2 C006 S001 108.8(6) . . ? C2 C006 N005 125.8(5) . . ? C1 C0 N003 115.0(12) . . ? C006 C2 N004 117.1(9) . . ? C0 C1 S002 107.3(7) . . ? C0 C1 N1 124.2(7) . . ? N1 C1 S002 128.5(4) . . ? N1 N1 C1 112.1(5) 3_666 . ? 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 S001 N003 1.675(2) . ? S001 C006 1.716(5) . ? S002 N004 1.643(4) . ? S002 C1 1.747(8) . ? N003 N004 1.3016(15) . ? N003 C0 1.393(11) . ? N004 C2 1.392(9) . ? N005 N005 1.271(5) 3_666 ? N005 C006 1.405(6) . ? C006 C2 1.278(13) . ? C0 C1 1.341(17) . ? C1 N1 1.392(9) . ? N1 N1 1.254(6) 3_666 ?