#------------------------------------------------------------------------------ #$Date: 2023-11-02 01:40:47 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287229 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247636.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_7247636 loop_ _publ_author_name 'Rizzuto, Felix' 'Pal, Shyam Chand' 'Kearns, Eleanor Rose' 'Hua, Carol' 'Solomon, Marcello B.' 'Doheny, Patrick W.' 'Faust, Thomas Benjamin' 'Kepert, Cameron J.' 'Das, Madhab C.' 'D'Alessandro, Deanna Michelle' _publ_section_title ; The Physical and Electronic Properties of Metal-Organic Frameworks Containing Dipyridylthiazolo[5,4-d]thiazole ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00541K _journal_year 2023 _chemical_formula_moiety 'C14 H8 N4 S2' _chemical_formula_sum 'C14 H8 N4 S2' _chemical_formula_weight 296.36 _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 _audit_creation_date 2023-05-02 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-05-03 deposited with the CCDC. 2023-10-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.544(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.4275(6) _cell_length_b 6.3040(4) _cell_length_c 11.7480(7) _cell_measurement_reflns_used 2871 _cell_measurement_temperature 150.15 _cell_measurement_theta_max 29.4610 _cell_measurement_theta_min 3.6340 _cell_volume 622.94(7) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _diffrn_ambient_temperature 150.15 _diffrn_detector_area_resol_mean 10.5861 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.900 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.900 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5958 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.900 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.058 _diffrn_reflns_theta_min 3.475 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.420 _exptl_absorpt_correction_T_max 0.9552 _exptl_absorpt_correction_T_min 0.8601 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.580 _exptl_crystal_description needle _exptl_crystal_F_000 304 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.430 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.074 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 1645 _refine_ls_number_restraints 18 _refine_ls_restrained_S_all 1.309 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0418 _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^)+(0.0516P)^2^+0.1932P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1004 _refine_ls_wR_factor_ref 0.1072 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1376 _reflns_number_total 1645 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00541k2.cif _cod_data_source_block p21c_CCDC1 _cod_database_code 7247636 _shelx_shelxl_version_number 2019/3 _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 0.955 _shelx_estimated_absorpt_t_min 0.860 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2. Restrained distances N1-C4 \\sim C4-C2 \\sim C2-C3 \\sim C3-C5 \\sim C5-C1 \\sim C1-N1 with sigma of 0.1 3. Restrained planarity N1, C4, C2, C3, C5, C1 with sigma of 0.1 4.a Aromatic/amide H refined with riding coordinates: C4(H4), C2(H2), C5(H5), C1(H1) ; _shelx_res_file ; TITL p21c in P2(1)/c p21c.res created by SHELXL-2019/3 at 09:57:42 on 02-May-2023 CELL 0.71073 8.4275 6.304 11.748 90 93.544 90 ZERR 2 0.0006 0.0004 0.0007 0 0.006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N S UNIT 28 16 8 4 FLAT N1 C4 C2 C3 C5 C1 SADI 0.1 N1 C4 C4 C2 C2 C3 C3 C5 C5 C1 C1 N1 L.S. 4 PLAN 5 SIZE 0.11 0.13 0.37 TEMP -123 CONF BOND $H fmap 2 MORE -1 ACTA MERG 2 REM REM REM WGHT 0.051600 0.193200 FVAR 0.82974 N2 3 0.113399 0.218964 0.558076 11.00000 0.02591 0.02208 = 0.02186 -0.00168 0.00099 -0.00479 N1 3 0.439040 0.802206 0.381501 11.00000 0.03258 0.02515 = 0.02462 0.00326 -0.00193 -0.00677 C7 1 -0.020120 -0.043074 0.447080 11.00000 0.02377 0.02163 = 0.01943 -0.00041 0.00123 -0.00269 C6 1 0.147042 0.269348 0.453868 11.00000 0.02203 0.02072 = 0.02057 -0.00110 -0.00002 -0.00092 S1 4 0.065203 0.105653 0.344134 11.00000 0.03120 0.02531 = 0.01779 -0.00071 0.00171 -0.00910 C4 1 0.284085 0.603782 0.511119 11.00000 0.02715 0.02364 = 0.02039 -0.00137 0.00206 -0.00285 AFIX 43 H4 2 0.246424 0.590169 0.585335 11.00000 -1.20000 AFIX 0 C2 1 0.307236 0.479356 0.320760 11.00000 0.02704 0.02475 = 0.01886 -0.00135 -0.00100 -0.00131 AFIX 43 H2 2 0.283961 0.380128 0.261193 11.00000 -1.20000 AFIX 0 C3 1 0.246448 0.452419 0.427375 11.00000 0.01840 0.01926 = 0.02295 0.00007 -0.00165 0.00053 C5 1 0.377561 0.774307 0.483651 11.00000 0.03058 0.02317 = 0.02394 -0.00271 0.00049 -0.00481 AFIX 43 H5 2 0.399963 0.878861 0.540628 11.00000 -1.20000 AFIX 0 C1 1 0.402237 0.653839 0.303605 11.00000 0.03252 0.02993 = 0.01814 0.00204 0.00325 -0.00513 AFIX 43 H1 2 0.444368 0.669006 0.230888 11.00000 -1.20000 AFIX 0 HKLF 4 REM p21c in P2(1)/c REM wR2 = 0.1072, GooF = S = 1.077, Restrained GooF = 1.309 for all data REM R1 = 0.0418 for 1376 Fo > 4sig(Fo) and 0.0531 for all 1645 data REM 91 parameters refined using 18 restraints END WGHT 0.0516 0.1934 REM Highest difference peak 0.430, deepest hole -0.226, 1-sigma level 0.074 Q1 1 0.2502 0.4709 0.3682 11.00000 0.05 0.43 Q2 1 0.0000 0.0000 0.5000 10.50000 0.05 0.41 Q3 1 0.1268 0.1926 0.4077 11.00000 0.05 0.40 Q4 1 0.3804 0.7679 0.3437 11.00000 0.05 0.40 Q5 1 0.2031 0.3699 0.4335 11.00000 0.05 0.39 ; _shelx_res_checksum 73800 _olex2_submission_special_instructions 'No special instructions were received' 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 N2 N 0.11340(19) 0.2190(2) 0.55808(12) 0.0233(3) Uani 1 1 d . . . . . N1 N 0.4390(2) 0.8022(3) 0.38150(13) 0.0276(4) Uani 1 1 d D . . . . C7 C -0.0201(2) -0.0431(3) 0.44708(14) 0.0216(4) Uani 1 1 d . . . . . C6 C 0.1470(2) 0.2693(3) 0.45387(14) 0.0212(4) Uani 1 1 d . . . . . S1 S 0.06520(6) 0.10565(7) 0.34413(4) 0.02476(17) Uani 1 1 d . . . . . C4 C 0.2841(2) 0.6038(3) 0.51112(15) 0.0237(4) Uani 1 1 d D . . . . H4 H 0.246424 0.590169 0.585335 0.028 Uiso 1 1 calc R U . . . C2 C 0.3072(2) 0.4794(3) 0.32076(14) 0.0237(4) Uani 1 1 d D . . . . H2 H 0.283961 0.380128 0.261193 0.028 Uiso 1 1 calc R U . . . C3 C 0.2464(2) 0.4524(3) 0.42737(14) 0.0203(4) Uani 1 1 d D . . . . C5 C 0.3776(2) 0.7743(3) 0.48365(16) 0.0259(4) Uani 1 1 d D . . . . H5 H 0.399963 0.878861 0.540628 0.031 Uiso 1 1 calc R U . . . C1 C 0.4022(2) 0.6538(3) 0.30361(15) 0.0268(4) Uani 1 1 d D . . . . H1 H 0.444368 0.669006 0.230888 0.032 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 N2 0.0259(9) 0.0221(8) 0.0219(7) -0.0017(6) 0.0010(6) -0.0048(6) N1 0.0326(9) 0.0251(8) 0.0246(8) 0.0033(6) -0.0019(7) -0.0068(7) C7 0.0238(10) 0.0216(8) 0.0194(8) -0.0004(7) 0.0012(7) -0.0027(7) C6 0.0220(9) 0.0207(8) 0.0206(8) -0.0011(7) 0.0000(7) -0.0009(7) S1 0.0312(3) 0.0253(3) 0.0178(2) -0.00071(17) 0.00171(18) -0.00910(19) C4 0.0271(10) 0.0236(9) 0.0204(8) -0.0014(7) 0.0021(7) -0.0029(7) C2 0.0270(10) 0.0248(9) 0.0189(8) -0.0014(7) -0.0010(7) -0.0013(8) C3 0.0184(9) 0.0193(8) 0.0230(8) 0.0001(7) -0.0017(7) 0.0005(7) C5 0.0306(11) 0.0232(9) 0.0239(9) -0.0027(7) 0.0005(8) -0.0048(8) C1 0.0325(11) 0.0299(10) 0.0181(8) 0.0020(7) 0.0032(7) -0.0051(8) 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 C6 N2 C7 108.28(15) . 3_556 ? C1 N1 C5 115.74(16) . . ? N2 C7 C7 118.1(2) 3_556 3_556 ? N2 C7 S1 132.73(13) 3_556 . ? C7 C7 S1 109.18(18) 3_556 . ? N2 C6 S1 116.37(14) . . ? N2 C6 C3 123.09(16) . . ? C3 C6 S1 120.54(12) . . ? C7 S1 C6 88.08(8) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C5 C4 C3 118.42(16) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C1 C2 C3 118.47(16) . . ? C4 C3 C6 119.73(15) . . ? C2 C3 C6 122.14(16) . . ? C2 C3 C4 118.12(17) . . ? N1 C5 C4 124.42(17) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? N1 C1 C2 124.82(16) . . ? N1 C1 H1 117.6 . . ? C2 C1 H1 117.6 . . ? 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 N2 C7 1.358(2) 3_556 ? N2 C6 1.313(2) . ? N1 C5 1.348(2) . ? N1 C1 1.332(2) . ? C7 C7 1.380(3) 3_556 ? C7 S1 1.7223(18) . ? C6 S1 1.7586(18) . ? C6 C3 1.471(2) . ? C4 H4 0.9500 . ? C4 C3 1.393(2) . ? C4 C5 1.383(3) . ? C2 H2 0.9500 . ? C2 C3 1.393(2) . ? C2 C1 1.383(3) . ? C5 H5 0.9500 . ? C1 H1 0.9500 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C7 S1 C6 -179.7(2) 3_556 . . . ? N2 C6 S1 C7 -0.33(16) . . . . ? N2 C6 C3 C4 -12.3(3) . . . . ? N2 C6 C3 C2 166.77(18) . . . . ? C7 N2 C6 S1 0.5(2) 3_556 . . . ? C7 N2 C6 C3 -179.93(16) 3_556 . . . ? C7 C7 S1 C6 0.07(19) 3_556 . . . ? S1 C6 C3 C4 167.29(14) . . . . ? S1 C6 C3 C2 -13.6(2) . . . . ? C3 C6 S1 C7 -179.94(16) . . . . ? C3 C4 C5 N1 -1.8(3) . . . . ? C3 C2 C1 N1 -1.0(3) . . . . ? C5 N1 C1 C2 0.3(3) . . . . ? C5 C4 C3 C6 -179.91(17) . . . . ? C5 C4 C3 C2 1.0(3) . . . . ? C1 N1 C5 C4 1.2(3) . . . . ? C1 C2 C3 C6 -178.76(17) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ?