#------------------------------------------------------------------------------ #$Date: 2020-05-07 00:15:04 +0300 (Thu, 07 May 2020) $ #$Revision: 251826 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240460.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_7240460 loop_ _publ_author_name 'Hachem, Hadi' 'Jeannin, olivier' 'Fourmigue, Marc' 'Barriere, Frederic' 'Lorcy, Dominique' _publ_section_title ; Halogen bonded metal bis(dithiolene) 2D frameworks ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00512F _journal_year 2020 _chemical_formula_moiety 'C4 H N O S3' _chemical_formula_sum 'C4 H N O S3' _chemical_formula_weight 175.24 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.3 _audit_creation_date 2017-09-13T15:37:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2020-04-02 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.329(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 3.9123(2) _cell_length_b 16.5922(11) _cell_length_c 9.7464(5) _cell_measurement_reflns_used 1811 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.3 _cell_measurement_theta_min 2.44 _cell_measurement_wavelength 0.71073 _cell_volume 626.00(6) _computing_cell_refinement 'Bruker APEX2 (Bruker, 2014)' _computing_data_collection 'Bruker APEX2 (Bruker, 2014)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2014)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _diffrn_ambient_temperature 296(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_orient_matrix_UB_11 0.246507 _diffrn_orient_matrix_UB_12 0.013522 _diffrn_orient_matrix_UB_13 -0.005958 _diffrn_orient_matrix_UB_21 -0.070828 _diffrn_orient_matrix_UB_22 0.055471 _diffrn_orient_matrix_UB_23 -0.032721 _diffrn_orient_matrix_UB_31 0.030867 _diffrn_orient_matrix_UB_32 0.019301 _diffrn_orient_matrix_UB_33 0.098218 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_unetI/netI 0.0309 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4310 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.443 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.083 _exptl_absorpt_correction_T_max 0.878 _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.859 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.336 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.07 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 82 _refine_ls_number_reflns 1415 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.09 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0377 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0262P)^2^+0.5735P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.0805 _reflns_Friedel_coverage 0 _reflns_number_gt 1183 _reflns_number_total 1415 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00512f2.cif _cod_data_source_block C4HNOS3 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240460 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL SIR92 run in space group P 21/n CELL 0.71073 3.9123 16.5922 9.7464 90.000 98.329 90.000 ZERR 2.00 0.0002 0.0011 0.0005 0.000 0.003 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S UNIT 16 4 4 4 12 MERG 2 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 10 TEMP 23.00 WGHT 0.026200 0.573500 FVAR 0.64873 S3 5 0.638238 0.299331 0.176222 11.00000 0.04300 0.02907 = 0.02994 0.00411 0.01118 -0.00147 S1 5 0.660150 0.113663 0.121776 11.00000 0.04540 0.03306 = 0.03198 -0.00471 0.01314 0.00213 S2 5 0.443715 0.094709 0.402047 11.00000 0.05024 0.02780 = 0.03446 0.00439 0.01466 -0.00063 N1 3 0.445979 0.261823 0.410216 11.00000 0.03977 0.02792 = 0.02848 -0.00031 0.00939 0.00203 C4 1 0.512905 0.322166 0.333484 11.00000 0.04327 0.02780 = 0.03175 0.00010 0.01065 0.00197 AFIX 43 H4 2 0.493881 0.375203 0.362304 11.00000 -1.20000 AFIX 0 O1 4 0.558943 -0.025466 0.238177 11.00000 0.10413 0.02627 = 0.06930 -0.00560 0.03289 -0.00065 C3 1 0.495530 0.191931 0.341413 11.00000 0.02938 0.02544 = 0.02502 0.00093 0.00423 -0.00046 C2 1 0.596150 0.199699 0.214049 11.00000 0.02869 0.02969 = 0.02662 0.00014 0.00430 -0.00024 C1 1 0.555557 0.046634 0.251746 11.00000 0.04440 0.03195 = 0.04370 -0.00300 0.01108 0.00010 HKLF 4 REM SIR92 run in space group P 21/n REM R1 = 0.0377 for 1183 Fo > 4sig(Fo) and 0.0485 for all 1415 data REM 82 parameters refined using 0 restraints END WGHT 0.0260 0.5761 REM Highest difference peak 0.336, deepest hole -0.229, 1-sigma level 0.070 Q1 1 0.6052 0.2400 0.1786 11.00000 0.05 0.34 Q2 1 0.4550 0.0632 0.3327 11.00000 0.05 0.32 Q3 1 0.4412 0.3183 0.2371 11.00000 0.05 0.32 Q4 1 0.8883 0.0975 0.1571 11.00000 0.05 0.30 Q5 1 0.4973 0.1922 0.2609 11.00000 0.05 0.29 Q6 1 0.5691 0.0791 0.1734 11.00000 0.05 0.28 Q7 1 0.5959 0.1650 0.1653 11.00000 0.05 0.28 Q8 1 0.8571 0.2918 0.2629 11.00000 0.05 0.25 Q9 1 0.7139 0.0043 0.2838 11.00000 0.05 0.24 Q10 1 0.5355 0.1056 0.0147 11.00000 0.05 0.24 Q11 1 0.3523 0.0865 0.0793 11.00000 0.05 0.23 Q12 1 0.5975 0.3147 0.2646 11.00000 0.05 0.22 Q13 1 0.4506 0.0024 0.2367 11.00000 0.05 0.22 Q14 1 0.3913 0.2799 0.3408 11.00000 0.05 0.21 Q15 1 0.4010 0.2622 0.1192 11.00000 0.05 0.20 Q16 1 0.8465 0.1179 0.0575 11.00000 0.05 0.20 Q17 1 0.6446 0.1007 0.4596 11.00000 0.05 0.20 Q18 1 0.8819 0.3037 0.1296 11.00000 0.05 0.20 Q19 1 0.3909 0.0173 0.2009 11.00000 0.05 0.20 Q20 1 0.9423 0.0290 0.0221 11.00000 0.05 0.20 Q21 1 0.6019 0.0021 0.1753 11.00000 0.05 0.19 Q22 1 0.4088 -0.0378 0.2860 11.00000 0.05 0.19 Q23 1 0.3388 0.2734 0.4692 11.00000 0.05 0.19 Q24 1 0.4992 -0.0174 0.1255 11.00000 0.05 0.19 Q25 1 0.4369 0.2228 0.3875 11.00000 0.05 0.18 ; _shelx_res_checksum 47811 loop_ _symmetry_equiv_pos_as_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 S3 S 0.63824(19) 0.29933(4) 0.17622(7) 0.03342(19) Uani 1 1 d . . . . . S1 S 0.66015(19) 0.11366(4) 0.12178(7) 0.0361(2) Uani 1 1 d . . . . . S2 S 0.4437(2) 0.09471(4) 0.40205(7) 0.0367(2) Uani 1 1 d . . . . . N1 N 0.4460(6) 0.26182(13) 0.4102(2) 0.0316(5) Uani 1 1 d . . . . . C4 C 0.5129(7) 0.32217(17) 0.3335(3) 0.0338(6) Uani 1 1 d . . . . . H4 H 0.4939 0.3752 0.3623 0.041 Uiso 1 1 calc R U . . . O1 O 0.5589(7) -0.02547(13) 0.2382(2) 0.0646(7) Uani 1 1 d . . . . . C3 C 0.4955(6) 0.19193(14) 0.3414(2) 0.0266(5) Uani 1 1 d . . . . . C2 C 0.5962(7) 0.19970(15) 0.2140(3) 0.0283(5) Uani 1 1 d . . . . . C1 C 0.5556(8) 0.04663(18) 0.2517(3) 0.0396(7) Uani 1 1 d . . . . . 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 S3 0.0430(4) 0.0291(4) 0.0299(3) 0.0041(3) 0.0112(3) -0.0015(3) S1 0.0454(4) 0.0331(4) 0.0320(3) -0.0047(3) 0.0131(3) 0.0021(3) S2 0.0502(4) 0.0278(4) 0.0345(4) 0.0044(3) 0.0147(3) -0.0006(3) N1 0.0398(13) 0.0279(12) 0.0285(11) -0.0003(9) 0.0094(9) 0.0020(10) C4 0.0433(17) 0.0278(13) 0.0317(13) 0.0001(11) 0.0107(12) 0.0020(12) O1 0.104(2) 0.0263(12) 0.0693(16) -0.0056(11) 0.0329(15) -0.0006(12) C3 0.0294(13) 0.0254(13) 0.0250(12) 0.0009(10) 0.0042(10) -0.0005(10) C2 0.0287(13) 0.0297(14) 0.0266(12) 0.0001(11) 0.0043(10) -0.0002(10) C1 0.0444(17) 0.0320(16) 0.0437(16) -0.0030(13) 0.0111(13) 0.0001(12) 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 0 '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' O O 0.0106 0.006 '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 C2 S3 C4 88.39(12) . . ? C2 S1 C1 94.62(12) . . ? C3 S2 C1 94.67(13) . . ? C4 N1 C3 108.5(2) . . ? N1 C4 S3 116.8(2) . . ? N1 C4 H4 121.6 . . ? S3 C4 H4 121.6 . . ? C2 C3 N1 116.6(2) . . ? C2 C3 S2 117.43(19) . . ? N1 C3 S2 126.01(18) . . ? C3 C2 S3 109.77(18) . . ? C3 C2 S1 118.69(19) . . ? S3 C2 S1 131.54(15) . . ? O1 C1 S1 122.4(2) . . ? O1 C1 S2 123.0(2) . . ? S1 C1 S2 114.59(16) . . ? 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 S3 C2 1.707(3) . ? S3 C4 1.718(3) . ? S1 C2 1.725(3) . ? S1 C1 1.777(3) . ? S2 C3 1.740(2) . ? S2 C1 1.777(3) . ? N1 C4 1.299(3) . ? N1 C3 1.367(3) . ? C4 H4 0.93 . ? O1 C1 1.204(3) . ? C3 C2 1.362(4) . ? 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 C3 N1 C4 S3 -0.1(3) . . . . ? C2 S3 C4 N1 0.4(2) . . . . ? C4 N1 C3 C2 -0.4(3) . . . . ? C4 N1 C3 S2 179.2(2) . . . . ? C1 S2 C3 C2 -0.5(2) . . . . ? C1 S2 C3 N1 179.8(2) . . . . ? N1 C3 C2 S3 0.7(3) . . . . ? S2 C3 C2 S3 -178.97(13) . . . . ? N1 C3 C2 S1 -179.60(18) . . . . ? S2 C3 C2 S1 0.7(3) . . . . ? C4 S3 C2 C3 -0.6(2) . . . . ? C4 S3 C2 S1 179.8(2) . . . . ? C1 S1 C2 C3 -0.4(2) . . . . ? C1 S1 C2 S3 179.1(2) . . . . ? C2 S1 C1 O1 179.7(3) . . . . ? C2 S1 C1 S2 0.07(18) . . . . ? C3 S2 C1 O1 -179.4(3) . . . . ? C3 S2 C1 S1 0.21(18) . . . . ?