#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:14 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160217.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_7160217 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 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 2024-07-09 _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 95.829(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.2855(12) _cell_length_b 4.9987(3) _cell_length_c 11.3283(7) _cell_measurement_reflns_used 2648 _cell_measurement_temperature 292.95(10) _cell_measurement_theta_max 27.3360 _cell_measurement_theta_min 2.2800 _cell_volume 1030.10(11) _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 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 0.996 _diffrn_measured_fraction_theta_max 0.870 _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 -102.00 -9.00 0.50 1.01 -- -21.77 -42.00 106.00 186 2 \w -1.00 25.00 0.50 1.01 -- -21.77 -99.00 30.00 52 3 \w -5.00 36.00 0.50 1.01 -- -21.77 -99.00 0.00 82 4 \w -12.00 36.00 0.50 1.01 -- -21.77 -99.00-120.00 96 5 \w -40.00 51.00 0.50 1.01 -- -21.77 42.00-100.00 182 6 \w 47.00 101.00 0.50 1.01 -- 21.93 178.00 150.00 108 ; _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 -0.0316475000 _diffrn_orient_matrix_UB_12 0.0722043000 _diffrn_orient_matrix_UB_13 -0.0230426000 _diffrn_orient_matrix_UB_21 -0.0122997000 _diffrn_orient_matrix_UB_22 0.0038856000 _diffrn_orient_matrix_UB_23 0.0574333000 _diffrn_orient_matrix_UB_31 0.0191094000 _diffrn_orient_matrix_UB_32 0.1220360000 _diffrn_orient_matrix_UB_33 0.0118586000 _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 0.0279 _diffrn_reflns_av_unetI/netI 0.0424 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.870 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6044 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.870 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.795 _diffrn_reflns_theta_min 2.239 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59482 _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 1.446 _exptl_crystal_description block _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.347 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.064 _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 129 _refine_ls_number_reflns 2342 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0559 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+0.6087P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1542 _refine_ls_wR_factor_ref 0.1738 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1600 _reflns_number_total 2342 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01573h2.cif _cod_data_source_block exp_2955_auto _cod_original_cell_volume 1030.08(11) _cod_database_code 7160217 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C8H8N4S2 _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 0.953 _shelx_estimated_absorpt_t_min 0.699 _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: C3(H3), C11(H11) 2.b Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C) ; _shelx_res_file ; TITL exp_2955_auto_a.res in P2(1)/c exp_2955_auto.res created by SHELXL-2018/3 at 11:37:09 on 09-Jul-2024 REM Old TITL exp_2955_auto in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.163, Rweak 0.260, Alpha 0.020 REM 0.191 for 240 systematic absences, Orientation as input REM Formula found by SHELXT: C14 N12 S1 CELL 0.71073 18.285507 4.998659 11.328251 90 95.8292 90 ZERR 4 0.001234 0.000256 0.000676 0 0.006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N S UNIT 32 32 16 8 L.S. 4 PLAN 2 SIZE 0.1 0.15 0.8 TEMP 20 fmap 2 ACTA REM REM REM WGHT 0.077500 0.608700 FVAR 3.43893 S9 4 0.815437 0.834329 0.865509 11.00000 0.05999 0.06584 = 0.05230 -0.00170 0.00572 0.00075 S1 4 0.698775 0.147123 0.514102 11.00000 0.08117 0.09361 = 0.05341 -0.01161 0.00168 -0.00398 N6 3 0.737079 0.430714 0.721916 11.00000 0.05896 0.06842 = 0.04926 0.00179 0.00017 0.00273 N7 3 0.787032 0.519311 0.664757 11.00000 0.05770 0.06872 = 0.05061 0.00475 0.00110 0.00726 N12 3 0.888654 0.806941 0.683172 11.00000 0.06270 0.07375 = 0.05245 -0.00100 0.01286 -0.01078 N5 3 0.631445 -0.071978 0.513086 11.00000 0.07926 0.08602 = 0.07623 -0.02180 -0.00951 0.00049 C8 1 0.830887 0.710875 0.727884 11.00000 0.05498 0.05703 = 0.04902 0.00334 -0.00072 0.00551 C10 1 0.892295 1.029588 0.864909 11.00000 0.05570 0.04895 = 0.05738 0.00449 -0.00322 0.00667 C3 1 0.639903 0.097526 0.703259 11.00000 0.05411 0.07451 = 0.05317 -0.00253 0.00127 0.00165 AFIX 43 H3 2 0.627545 0.113627 0.780577 11.00000 -1.20000 AFIX 0 C2 1 0.692954 0.238381 0.658354 11.00000 0.05430 0.06318 = 0.05112 -0.00114 -0.00788 0.00904 C4 1 0.604839 -0.080746 0.616512 11.00000 0.05446 0.06094 = 0.08103 -0.00486 -0.00854 0.00873 C11 1 0.922850 0.986052 0.761663 11.00000 0.05665 0.07034 = 0.06836 0.00224 0.00463 -0.00888 AFIX 43 H11 2 0.965350 1.074852 0.745252 11.00000 -1.20000 AFIX 0 C13 1 0.919018 1.210925 0.964844 11.00000 0.07555 0.06113 = 0.07216 -0.00686 -0.00311 0.00055 AFIX 137 H13A 2 0.881092 1.336662 0.978483 11.00000 -1.50000 H13B 2 0.961762 1.305683 0.944980 11.00000 -1.50000 H13C 2 0.931381 1.107014 1.035318 11.00000 -1.50000 AFIX 0 C14 1 0.542815 -0.264877 0.636537 11.00000 0.07677 0.07858 = 0.13284 -0.01094 -0.00664 -0.01085 AFIX 137 H14A 2 0.496976 -0.181387 0.608872 11.00000 -1.50000 H14B 2 0.543686 -0.302844 0.719740 11.00000 -1.50000 H14C 2 0.547974 -0.428582 0.593852 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_2955_auto_a.res in P2(1)/c REM wR2 = 0.1738, GooF = S = 1.052, Restrained GooF = 1.052 for all data REM R1 = 0.0559 for 1600 Fo > 4sig(Fo) and 0.0810 for all 2342 data REM 129 parameters refined using 0 restraints END WGHT 0.0774 0.6097 REM Highest difference peak 0.347, deepest hole -0.364, 1-sigma level 0.064 Q1 1 0.8219 0.7284 0.8028 11.00000 0.05 0.35 Q2 1 0.6984 0.1929 0.5950 11.00000 0.05 0.28 ; _shelx_res_checksum 18548 _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 2.592 _oxdiff_exptl_absorpt_empirical_full_min 0.351 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 S9 S 0.81544(5) 0.83433(16) 0.86551(7) 0.0594(3) Uani 1 1 d . . . . . S1 S 0.69877(6) 0.1471(2) 0.51410(8) 0.0764(3) Uani 1 1 d . . . . . N6 N 0.73708(15) 0.4307(5) 0.7219(2) 0.0592(7) Uani 1 1 d . . . . . N7 N 0.78703(15) 0.5193(5) 0.6648(2) 0.0593(7) Uani 1 1 d . . . . . N12 N 0.88865(16) 0.8069(5) 0.6832(2) 0.0625(7) Uani 1 1 d . . . . . N5 N 0.63145(19) -0.0720(7) 0.5131(3) 0.0817(9) Uani 1 1 d . . . . . C8 C 0.83089(18) 0.7109(6) 0.7279(3) 0.0541(7) Uani 1 1 d . . . . . C10 C 0.89230(17) 1.0296(6) 0.8649(3) 0.0546(7) Uani 1 1 d . . . . . C3 C 0.63990(18) 0.0975(7) 0.7033(3) 0.0609(8) Uani 1 1 d . . . . . H3 H 0.627545 0.113627 0.780577 0.073 Uiso 1 1 calc R U . . . C2 C 0.69295(18) 0.2384(6) 0.6584(3) 0.0571(8) Uani 1 1 d . . . . . C4 C 0.60484(19) -0.0807(7) 0.6165(3) 0.0665(9) Uani 1 1 d . . . . . C11 C 0.92285(19) 0.9861(7) 0.7617(3) 0.0652(9) Uani 1 1 d . . . . . H11 H 0.965350 1.074852 0.745252 0.078 Uiso 1 1 calc R U . . . C13 C 0.9190(2) 1.2109(7) 0.9648(3) 0.0703(9) Uani 1 1 d . . . . . H13A H 0.881092 1.336662 0.978483 0.106 Uiso 1 1 calc R U . . . H13B H 0.961762 1.305683 0.944980 0.106 Uiso 1 1 calc R U . . . H13C H 0.931381 1.107014 1.035318 0.106 Uiso 1 1 calc R U . . . C14 C 0.5428(2) -0.2649(9) 0.6365(5) 0.0972(14) Uani 1 1 d . . . . . H14A H 0.496976 -0.181387 0.608872 0.146 Uiso 1 1 calc R U . . . H14B H 0.543686 -0.302844 0.719740 0.146 Uiso 1 1 calc R U . . . H14C H 0.547974 -0.428582 0.593852 0.146 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 S9 0.0600(5) 0.0658(5) 0.0523(5) -0.0017(3) 0.0057(4) 0.0007(4) S1 0.0812(7) 0.0936(7) 0.0534(5) -0.0116(4) 0.0017(5) -0.0040(5) N6 0.0590(16) 0.0684(15) 0.0493(14) 0.0018(12) 0.0002(12) 0.0027(13) N7 0.0577(16) 0.0687(16) 0.0506(15) 0.0047(12) 0.0011(12) 0.0073(13) N12 0.0627(17) 0.0737(17) 0.0524(16) -0.0010(12) 0.0129(13) -0.0108(14) N5 0.079(2) 0.086(2) 0.076(2) -0.0218(17) -0.0095(17) 0.0005(17) C8 0.0550(18) 0.0570(16) 0.0490(17) 0.0033(13) -0.0007(14) 0.0055(13) C10 0.0557(18) 0.0489(15) 0.0574(18) 0.0045(13) -0.0032(14) 0.0067(13) C3 0.0541(19) 0.075(2) 0.0532(18) -0.0025(15) 0.0013(14) 0.0016(15) C2 0.0543(19) 0.0632(17) 0.0511(18) -0.0011(14) -0.0079(14) 0.0090(14) C4 0.054(2) 0.0609(18) 0.081(3) -0.0049(17) -0.0085(18) 0.0087(15) C11 0.057(2) 0.070(2) 0.068(2) 0.0022(16) 0.0046(17) -0.0089(16) C13 0.076(2) 0.0611(19) 0.072(2) -0.0069(16) -0.0031(18) 0.0006(16) C14 0.077(3) 0.079(2) 0.133(4) -0.011(3) -0.007(3) -0.011(2) 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 C10 S9 C8 89.46(16) . . ? N5 S1 C2 93.73(18) . . ? N7 N6 C2 112.8(3) . . ? N6 N7 C8 112.8(3) . . ? C8 N12 C11 108.8(3) . . ? C4 N5 S1 111.1(3) . . ? N7 C8 S9 124.7(2) . . ? N12 C8 S9 115.5(2) . . ? N12 C8 N7 119.8(3) . . ? C11 C10 S9 108.7(2) . . ? C11 C10 C13 128.0(3) . . ? C13 C10 S9 123.3(3) . . ? C2 C3 C4 111.0(3) . . ? N6 C2 S1 125.7(3) . . ? C3 C2 S1 109.9(3) . . ? C3 C2 N6 124.4(3) . . ? N5 C4 C3 114.3(3) . . ? N5 C4 C14 120.7(4) . . ? C3 C4 C14 125.0(4) . . ? C10 C11 N12 117.5(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 S9 C8 1.726(3) . ? S9 C10 1.712(3) . ? S1 N5 1.647(4) . ? S1 C2 1.710(3) . ? N6 N7 1.253(4) . ? N6 C2 1.406(4) . ? N7 C8 1.398(4) . ? N12 C8 1.308(4) . ? N12 C11 1.368(4) . ? N5 C4 1.314(5) . ? C10 C11 1.364(5) . ? C10 C13 1.493(5) . ? C3 C2 1.340(5) . ? C3 C4 1.429(5) . ? C4 C14 1.496(6) . ?