#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:14 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160214.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_7160214 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 monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-03-07 _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 104.253(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.4747(2) _cell_length_b 15.4161(6) _cell_length_c 10.5241(4) _cell_measurement_reflns_used 7269 _cell_measurement_temperature 199.95(10) _cell_measurement_theta_max 31.0510 _cell_measurement_theta_min 2.6160 _cell_volume 860.88(6) _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 199.95(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 0.869 _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 -67.00 20.00 0.50 0.53 -- 5.68 -53.00-109.00 174 2 \w -18.00 38.00 0.50 0.53 -- 5.68 -99.00 -30.00 112 3 \w -67.00 28.00 0.50 0.53 -- 5.68 -77.00 120.00 190 4 \w -67.00 -10.00 0.50 0.53 -- 5.68 -37.00 30.00 114 5 \w -8.00 78.00 0.50 0.53 -- 5.68 53.00 34.00 172 6 \w -18.00 68.00 0.50 0.53 -- -5.45 37.00 -30.00 172 7 \w -79.00 7.00 0.50 0.53 -- -5.45 -37.00 150.00 172 8 \w -18.00 27.00 0.50 0.53 -- -5.45 -99.00-120.00 90 9 \w -18.00 27.00 0.50 0.53 -- -5.45 -99.00-150.00 90 ; _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 -0.0032700000 _diffrn_orient_matrix_UB_12 0.0232772000 _diffrn_orient_matrix_UB_13 0.0577090000 _diffrn_orient_matrix_UB_21 -0.1200239000 _diffrn_orient_matrix_UB_22 -0.0179727000 _diffrn_orient_matrix_UB_23 -0.0016820000 _diffrn_orient_matrix_UB_31 0.0587734000 _diffrn_orient_matrix_UB_32 -0.0353829000 _diffrn_orient_matrix_UB_33 0.0387695000 _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 0.0286 _diffrn_reflns_av_unetI/netI 0.0226 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.869 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9818 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.799 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 31.261 _diffrn_reflns_theta_min 2.642 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Mova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.70393 _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 1.468 _exptl_crystal_description block _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.346 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details ; Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 118 _refine_ls_number_reflns 2236 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0347 _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^)+(0.0521P)^2^+0.1631P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.0908 _reflns_Friedel_coverage 0.833 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.729 _reflns_number_gt 2044 _reflns_number_total 2236 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01573h2.cif _cod_data_source_block exp_2735_autored _cod_database_code 7160214 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C8H6N4S _chemical_oxdiff_usercomment '200K, cis_Ph_NN_124N2S' _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 0.956 _shelx_estimated_absorpt_t_min 0.845 _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.a Aromatic/amide H refined with riding coordinates: C2(H2), C6(H6), C7(H7), C4(H4), C8(H8), C5(H5) ; _shelx_res_file ; TITL exp_2735_autored_a.res in Cc exp_2735_autored.res created by SHELXL-2018/3 at 11:13:39 on 07-Mar-2024 REM Old TITL exp_2735_autored in C1 REM SHELXT solution in Cc: R1 0.183, Rweak 0.053, Alpha 0.004 REM 0.972 for 35 systematic absences, Orientation as input REM Flack x = 0.107 ( 0.028 ) from 811 Parsons' quotients REM Formula found by SHELXT: C8 N1 S CELL 0.71073 5.4747 15.4161 10.5241 90 104.253 90 ZERR 4 0.0002 0.0006 0.0004 0 0.004 0 LATT -7 SYMM +X,-Y,0.5+Z SFAC C H N S UNIT 32 24 16 4 L.S. 4 PLAN 5 SIZE 0.14 0.17 0.53 TEMP -73.2(1) fmap 2 acta REM REM REM WGHT 0.052100 0.163100 FVAR 0.81992 S1 4 0.260010 0.571761 0.457459 11.00000 0.02196 0.10559 = 0.04437 -0.02001 0.00640 0.00043 N2 3 0.651106 0.534207 0.378043 11.00000 0.02861 0.06028 = 0.04292 -0.00703 0.00860 0.00448 N4 3 0.765690 0.637780 0.674927 11.00000 0.03040 0.06116 = 0.03589 0.00342 0.00378 0.00046 N3 3 0.771808 0.578034 0.596361 11.00000 0.02351 0.05947 = 0.03534 0.00204 0.00397 0.00235 N1 3 0.447723 0.515106 0.276366 11.00000 0.03819 0.06390 = 0.04261 -0.01408 0.00566 0.00036 C3 1 0.578865 0.705549 0.643680 11.00000 0.03459 0.04761 = 0.03087 -0.00279 -0.00019 -0.00243 C1 1 0.581447 0.566229 0.477640 11.00000 0.02253 0.04353 = 0.03515 0.00252 0.00509 0.00308 C2 1 0.239627 0.783389 0.696165 11.00000 0.04368 0.05227 = 0.04632 -0.00881 0.01096 -0.00150 AFIX 43 H2 2 0.120401 0.789765 0.747586 11.00000 -1.20000 AFIX 0 C6 1 0.239064 0.841385 0.595623 11.00000 0.05213 0.04306 = 0.05086 -0.00319 0.00084 -0.00016 AFIX 43 H6 2 0.120706 0.887604 0.578567 11.00000 -1.20000 AFIX 0 C7 1 0.411458 0.831787 0.520096 11.00000 0.05706 0.05177 = 0.04286 0.00877 0.00079 -0.01225 AFIX 43 H7 2 0.413891 0.872346 0.452457 11.00000 -1.20000 AFIX 0 C4 1 0.412152 0.716330 0.722311 11.00000 0.04401 0.04692 = 0.03495 -0.00062 0.00771 -0.00137 AFIX 43 H4 2 0.416367 0.678005 0.793507 11.00000 -1.20000 AFIX 0 C8 1 0.579782 0.763641 0.542508 11.00000 0.04422 0.06103 = 0.03509 0.00236 0.00656 -0.01102 AFIX 43 H8 2 0.695539 0.756383 0.489297 11.00000 -1.20000 AFIX 0 C5 1 0.235334 0.530262 0.305214 11.00000 0.03209 0.04643 = 0.04013 -0.00491 0.00217 -0.00182 AFIX 43 H5 2 0.077406 0.519041 0.245770 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_2735_autored_a.res in Cc REM wR2 = 0.0908, GooF = S = 1.081, Restrained GooF = 1.081 for all data REM R1 = 0.0347 for 2044 Fo > 4sig(Fo) and 0.0383 for all 2236 data REM 118 parameters refined using 2 restraints END WGHT 0.0521 0.1618 REM Highest difference peak 0.346, deepest hole -0.169, 1-sigma level 0.046 Q1 1 0.3012 0.6106 0.4117 11.00000 0.05 0.35 Q2 1 0.2229 0.5223 0.4000 11.00000 0.05 0.31 Q3 1 0.3108 0.5188 0.4624 11.00000 0.05 0.23 Q4 1 0.6285 0.5077 0.4397 11.00000 0.05 0.20 Q5 1 0.6149 0.5766 0.3901 11.00000 0.05 0.19 ; _shelx_res_checksum 71087 _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 1.385 _oxdiff_exptl_absorpt_empirical_full_min 0.680 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, 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 S1 S 0.26001(10) 0.57176(6) 0.45746(7) 0.0576(2) Uani 1 1 d . . . . . N2 N 0.6511(4) 0.53421(17) 0.3780(2) 0.0440(5) Uani 1 1 d . . . . . N4 N 0.7657(4) 0.63778(16) 0.6749(2) 0.0433(5) Uani 1 1 d . . . . . N3 N 0.7718(4) 0.57803(14) 0.5964(2) 0.0400(5) Uani 1 1 d . . . . . N1 N 0.4477(4) 0.51511(17) 0.2764(2) 0.0490(5) Uani 1 1 d . . . . . C3 C 0.5789(5) 0.70555(16) 0.6437(2) 0.0391(5) Uani 1 1 d . . . . . C1 C 0.5814(4) 0.56623(15) 0.4776(2) 0.0341(5) Uani 1 1 d . . . . . C2 C 0.2396(6) 0.78339(17) 0.6962(3) 0.0474(6) Uani 1 1 d . . . . . H2 H 0.120401 0.789765 0.747586 0.057 Uiso 1 1 calc R U . . . C6 C 0.2391(6) 0.84138(18) 0.5956(3) 0.0508(7) Uani 1 1 d . . . . . H6 H 0.120706 0.887604 0.578567 0.061 Uiso 1 1 calc R U . . . C7 C 0.4115(6) 0.8318(2) 0.5201(3) 0.0526(7) Uani 1 1 d . . . . . H7 H 0.413891 0.872346 0.452457 0.063 Uiso 1 1 calc R U . . . C4 C 0.4122(5) 0.71633(17) 0.7223(3) 0.0423(5) Uani 1 1 d . . . . . H4 H 0.416367 0.678005 0.793507 0.051 Uiso 1 1 calc R U . . . C8 C 0.5798(6) 0.76364(19) 0.5425(3) 0.0473(6) Uani 1 1 d . . . . . H8 H 0.695539 0.756383 0.489297 0.057 Uiso 1 1 calc R U . . . C5 C 0.2353(5) 0.53026(16) 0.3052(3) 0.0407(5) Uani 1 1 d . . . . . H5 H 0.077406 0.519041 0.245770 0.049 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 S1 0.0220(3) 0.1056(6) 0.0444(3) -0.0200(4) 0.0064(2) 0.0004(3) N2 0.0286(10) 0.0603(13) 0.0429(11) -0.0070(10) 0.0086(8) 0.0045(9) N4 0.0304(10) 0.0612(13) 0.0359(10) 0.0034(9) 0.0038(8) 0.0005(9) N3 0.0235(9) 0.0595(12) 0.0353(10) 0.0020(9) 0.0040(8) 0.0023(8) N1 0.0382(12) 0.0639(14) 0.0426(11) -0.0141(10) 0.0057(9) 0.0004(9) C3 0.0346(12) 0.0476(12) 0.0309(11) -0.0028(9) -0.0002(9) -0.0024(10) C1 0.0225(10) 0.0435(11) 0.0352(11) 0.0025(9) 0.0051(9) 0.0031(8) C2 0.0437(14) 0.0523(15) 0.0463(14) -0.0088(12) 0.0110(11) -0.0015(11) C6 0.0521(16) 0.0431(14) 0.0509(16) -0.0032(11) 0.0008(12) -0.0002(11) C7 0.0571(16) 0.0518(15) 0.0429(13) 0.0088(12) 0.0008(12) -0.0122(13) C4 0.0440(13) 0.0469(13) 0.0349(11) -0.0006(10) 0.0077(10) -0.0014(11) C8 0.0442(14) 0.0610(15) 0.0351(12) 0.0024(12) 0.0066(10) -0.0110(12) C5 0.0321(11) 0.0464(13) 0.0401(12) -0.0049(10) 0.0022(9) -0.0018(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 C5 S1 C1 86.52(13) . . ? C1 N2 N1 111.6(2) . . ? N3 N4 C3 121.2(2) . . ? N4 N3 C1 122.9(2) . . ? C5 N1 N2 112.4(2) . . ? C4 C3 N4 119.0(2) . . ? C4 C3 C8 120.5(3) . . ? C8 C3 N4 120.3(2) . . ? N2 C1 S1 114.44(18) . . ? N2 C1 N3 117.3(2) . . ? N3 C1 S1 127.24(18) . . ? C4 C2 C6 120.5(3) . . ? C7 C6 C2 119.8(3) . . ? C8 C7 C6 120.3(3) . . ? C2 C4 C3 119.3(2) . . ? C7 C8 C3 119.5(3) . . ? N1 C5 S1 115.0(2) . . ? 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 S1 C1 1.722(2) . ? S1 C5 1.699(3) . ? N2 N1 1.373(3) . ? N2 C1 1.298(3) . ? N4 N3 1.244(3) . ? N4 C3 1.442(3) . ? N3 C1 1.428(3) . ? N1 C5 1.293(4) . ? C3 C4 1.385(4) . ? C3 C8 1.392(4) . ? C2 C6 1.385(4) . ? C2 C4 1.382(4) . ? C6 C7 1.383(5) . ? C7 C8 1.379(5) . ?