#------------------------------------------------------------------------------ #$Date: 2016-08-07 11:29:25 +0300 (Sun, 07 Aug 2016) $ #$Revision: 185245 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/49/7224993.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_7224993 loop_ _publ_author_name 'Le Gal, Yann' 'Rajkumar, Mangaiyarkarasi' 'Vacher, Antoine' 'Dorcet, Vincent' 'Roisnel, Thierry' 'Fourmigu\'e, Marc' 'Barri\`ere, Fr\'ed\'eric' 'Guizouarn, Thierry' 'Lorcy, Dominique' _publ_section_title ; A sulfur-rich \p-electron acceptor derived from 5,5′-bithiazolidinylidene: charge-transfer complex vs. charge-transfer salt ; _journal_issue 21 _journal_name_full CrystEngComm _journal_page_first 3925 _journal_paper_doi 10.1039/C6CE00772D _journal_volume 18 _journal_year 2016 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C16 H10 N6 S4' _chemical_formula_sum 'C16 H10 N6 S4' _chemical_formula_weight 414.54 _chemical_name_systematic ; ? ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_update_record ; 2016-03-31 deposited with the CCDC. 2016-04-22 downloaded from the CCDC. ; _cell_angle_alpha 77.773(2) _cell_angle_beta 80.2040(10) _cell_angle_gamma 69.1100(10) _cell_formula_units_Z 1 _cell_length_a 5.3638(2) _cell_length_b 7.2562(3) _cell_length_c 12.7329(5) _cell_measurement_reflns_used 4978 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 3.05 _cell_measurement_wavelength 0.71073 _cell_volume 450.06(3) _computing_cell_refinement 'Bruker APEX2 (Bruker, 2014)' _computing_data_collection 'Bruker APEX2 (Bruker, 2014)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2014)' _computing_molecular_graphics 'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)' _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2016)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SIR97 (ALtomare et al., 1999)' _diffrn_ambient_temperature 294(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _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 0.0292 _diffrn_reflns_av_unetI/netI 0.0243 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7308 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.480 _diffrn_reflns_theta_min 3.046 _exptl_absorpt_coefficient_mu 0.541 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.529 _exptl_crystal_description prism _exptl_crystal_F_000 212 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.264 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2051 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0261 _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^)+(0.0357P)^2^+0.1161P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.0747 _reflns_number_gt 1872 _reflns_number_total 2051 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c6ce00772d2.cif _cod_data_source_block acceptor_1 _cod_depositor_comments ; The following automatic conversions were performed: '_space_group_crystal_system' value 'Triclinic' changed to 'triclinic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas Adding full bibliography for 7224990--7224994.cif. ; _cod_database_code 7224993 _shelx_res_file ; job.res created by SHELXL-2014/7 TITL import in P -1 CELL 0.71073 5.3638 7.2562 12.7329 77.773 80.204 69.110 ZERR 1.00 0.0002 0.0003 0.0005 0.002 0.001 0.001 LATT 1 SFAC C H N S UNIT 16 10 6 4 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP 21.00 WGHT 0.035700 0.116100 FVAR 0.86736 S1 4 0.691372 0.560934 0.183205 11.00000 0.04716 0.04319 = 0.04021 -0.00970 -0.00778 -0.02327 S2 4 0.317094 0.262059 0.041422 11.00000 0.03888 0.03491 = 0.03348 -0.00685 -0.00328 -0.01882 C1 1 0.473182 0.434391 0.044149 11.00000 0.03120 0.03120 = 0.03327 -0.00890 -0.00158 -0.01247 C2 1 0.541335 0.421398 0.151960 11.00000 0.03154 0.03190 = 0.03279 -0.00825 -0.00134 -0.01103 N3 3 0.462886 0.275381 0.224302 11.00000 0.03899 0.03613 = 0.03098 -0.00545 -0.00268 -0.01637 C4 1 0.495786 0.243543 0.340350 11.00000 0.05273 0.05223 = 0.03163 -0.00303 -0.00753 -0.02612 AFIX 23 H4A 2 0.643738 0.284508 0.348846 11.00000 -1.20000 H4B 2 0.539158 0.102303 0.369590 11.00000 -1.20000 AFIX 0 C5 1 0.243190 0.360980 0.402745 11.00000 0.07207 0.07149 = 0.04323 -0.02113 0.00765 -0.02974 AFIX 137 H5A 2 0.194883 0.500041 0.371601 11.00000 -1.50000 H5B 2 0.274371 0.344600 0.476732 11.00000 -1.50000 H5C 2 0.100078 0.312798 0.399483 11.00000 -1.50000 AFIX 0 C6 1 0.339896 0.178696 0.180679 11.00000 0.03273 0.03273 = 0.03476 -0.00685 -0.00091 -0.01104 C7 1 0.235484 0.030085 0.231843 11.00000 0.04172 0.03435 = 0.03943 -0.00482 -0.00072 -0.01645 C8 1 0.096281 -0.040224 0.171551 11.00000 0.04348 0.03836 = 0.04832 -0.00275 -0.00105 -0.01973 N9 3 -0.020844 -0.097785 0.127751 11.00000 0.06534 0.06621 = 0.07677 -0.00873 -0.01390 -0.03954 C10 1 0.250047 -0.064222 0.341773 11.00000 0.06559 0.04441 = 0.04570 -0.00457 -0.00228 -0.02834 N11 3 0.254341 -0.148669 0.428101 11.00000 0.11920 0.07177 = 0.04970 0.00590 -0.00991 -0.05493 HKLF 4 REM import in P -1 REM R1 = 0.0261 for 1872 Fo > 4sig(Fo) and 0.0292 for all 2051 data REM 119 parameters refined using 0 restraints END WGHT 0.0357 0.1161 REM Highest difference peak 0.264, deepest hole -0.156, 1-sigma level 0.042 Q1 1 0.5000 0.5000 0.0000 10.50000 0.05 0.26 Q2 1 0.5099 0.4399 0.0953 11.00000 0.05 0.25 Q3 1 0.2714 0.1028 0.2149 11.00000 0.05 0.23 Q4 1 0.4731 0.2678 0.2819 11.00000 0.05 0.22 Q5 1 0.3128 0.2222 0.1216 11.00000 0.05 0.21 Q6 1 0.5306 0.3378 0.1843 11.00000 0.05 0.20 Q7 1 0.5822 0.5031 0.1652 11.00000 0.05 0.18 Q8 1 0.1594 -0.0007 0.2035 11.00000 0.05 0.17 Q9 1 0.3539 0.3109 0.3612 11.00000 0.05 0.16 Q10 1 0.1995 0.0380 0.2863 11.00000 0.05 0.16 Q11 1 0.3685 0.2354 0.2056 11.00000 0.05 0.16 Q12 1 0.6556 0.5380 0.2682 11.00000 0.05 0.15 Q13 1 0.4155 0.3525 0.0399 11.00000 0.05 0.15 Q14 1 0.6491 0.6652 0.1157 11.00000 0.05 0.13 Q15 1 0.0276 0.3564 0.3950 11.00000 0.05 0.13 Q16 1 0.2077 -0.0191 0.3810 11.00000 0.05 0.12 Q17 1 0.0065 -0.0382 0.1992 11.00000 0.05 0.12 Q18 1 0.1114 -0.1098 0.1798 11.00000 0.05 0.12 Q19 1 0.2666 0.5113 0.4013 11.00000 0.05 0.12 Q20 1 0.2642 0.4198 0.4541 11.00000 0.05 0.12 ; _shelx_res_checksum 43114 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 S1 S 0.69137(7) 0.56093(5) 0.18320(3) 0.04038(12) Uani 1 1 d . . S2 S 0.31709(6) 0.26206(5) 0.04142(3) 0.03381(11) Uani 1 1 d . . C1 C 0.4732(2) 0.43439(18) 0.04415(10) 0.0310(3) Uani 1 1 d . . C2 C 0.5413(2) 0.42140(18) 0.15196(10) 0.0317(3) Uani 1 1 d . . N3 N 0.4629(2) 0.27538(16) 0.22430(9) 0.0344(2) Uani 1 1 d . . C4 C 0.4958(3) 0.2435(2) 0.34035(11) 0.0433(3) Uani 1 1 d . . H4A H 0.6437 0.2845 0.3488 0.052 Uiso 1 1 calc R U H4B H 0.5392 0.1023 0.3696 0.052 Uiso 1 1 calc R U C5 C 0.2432(4) 0.3610(3) 0.40274(14) 0.0605(5) Uani 1 1 d . . H5A H 0.1949 0.5000 0.3716 0.091 Uiso 1 1 calc R U H5B H 0.2744 0.3446 0.4767 0.091 Uiso 1 1 calc R U H5C H 0.1001 0.3128 0.3995 0.091 Uiso 1 1 calc R U C6 C 0.3399(3) 0.17870(19) 0.18068(11) 0.0335(3) Uani 1 1 d . . C7 C 0.2355(3) 0.0301(2) 0.23184(12) 0.0381(3) Uani 1 1 d . . C8 C 0.0963(3) -0.0402(2) 0.17155(13) 0.0428(3) Uani 1 1 d . . N9 N -0.0208(3) -0.0978(2) 0.12775(14) 0.0642(4) Uani 1 1 d . . C10 C 0.2500(4) -0.0642(2) 0.34177(13) 0.0500(4) Uani 1 1 d . . N11 N 0.2543(4) -0.1487(3) 0.42810(13) 0.0762(5) 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 S1 0.0472(2) 0.0432(2) 0.0402(2) -0.00970(15) -0.00778(15) -0.02327(16) S2 0.03888(19) 0.03491(18) 0.03348(19) -0.00685(13) -0.00328(13) -0.01882(14) C1 0.0312(6) 0.0312(6) 0.0333(6) -0.0089(5) -0.0016(5) -0.0125(5) C2 0.0315(6) 0.0319(6) 0.0328(7) -0.0082(5) -0.0013(5) -0.0110(5) N3 0.0390(6) 0.0361(6) 0.0310(6) -0.0054(4) -0.0027(4) -0.0164(5) C4 0.0527(8) 0.0522(8) 0.0316(7) -0.0030(6) -0.0075(6) -0.0261(7) C5 0.0721(11) 0.0715(12) 0.0432(9) -0.0211(8) 0.0077(8) -0.0297(9) C6 0.0327(6) 0.0327(6) 0.0348(7) -0.0068(5) -0.0009(5) -0.0110(5) C7 0.0417(7) 0.0343(6) 0.0394(7) -0.0048(5) -0.0007(6) -0.0165(5) C8 0.0435(8) 0.0384(7) 0.0483(8) -0.0028(6) -0.0010(6) -0.0197(6) N9 0.0653(10) 0.0662(10) 0.0768(11) -0.0087(8) -0.0139(8) -0.0395(8) C10 0.0656(10) 0.0444(8) 0.0457(9) -0.0046(7) -0.0023(7) -0.0283(7) N11 0.1192(15) 0.0718(11) 0.0497(9) 0.0059(8) -0.0099(9) -0.0549(11) 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 C1 S2 C6 90.00(6) . C1 C1 C2 123.98(15) 2_665 C1 C1 S2 124.49(13) 2_665 C2 C1 S2 111.53(9) . N3 C2 C1 110.89(11) . N3 C2 S1 124.72(10) . C1 C2 S1 124.40(10) . C6 N3 C2 114.67(11) . C6 N3 C4 124.49(11) . C2 N3 C4 120.68(11) . N3 C4 C5 111.36(13) . N3 C4 H4A 109.4 . C5 C4 H4A 109.4 . N3 C4 H4B 109.4 . C5 C4 H4B 109.4 . H4A C4 H4B 108.0 . C4 C5 H5A 109.5 . C4 C5 H5B 109.5 . H5A C5 H5B 109.5 . C4 C5 H5C 109.5 . H5A C5 H5C 109.5 . H5B C5 H5C 109.5 . N3 C6 C7 128.34(13) . N3 C6 S2 112.91(9) . C7 C6 S2 118.75(11) . C6 C7 C10 126.63(14) . C6 C7 C8 118.85(13) . C10 C7 C8 114.52(13) . N9 C8 C7 177.00(17) . N11 C10 C7 175.25(18) . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C2 1.6407(13) . S2 C1 1.7438(13) . S2 C6 1.7583(14) . C1 C1 1.373(3) 2_665 C1 C2 1.4555(18) . C2 N3 1.3859(16) . N3 C6 1.3623(17) . N3 C4 1.4775(17) . C4 C5 1.513(2) . C4 H4A 0.9700 . C4 H4B 0.9700 . C5 H5A 0.9600 . C5 H5B 0.9600 . C5 H5C 0.9600 . C6 C7 1.3820(19) . C7 C10 1.424(2) . C7 C8 1.428(2) . C8 N9 1.134(2) . C10 N11 1.139(2) . 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_4 C6 S2 C1 C1 -179.64(16) . 2_665 C6 S2 C1 C2 0.66(10) . . C1 C1 C2 N3 -179.93(15) 2_665 . S2 C1 C2 N3 -0.22(14) . . C1 C1 C2 S1 0.0(2) 2_665 . S2 C1 C2 S1 179.67(7) . . C1 C2 N3 C6 -0.53(16) . . S1 C2 N3 C6 179.58(9) . . C1 C2 N3 C4 -176.12(11) . . S1 C2 N3 C4 3.98(18) . . C6 N3 C4 C5 -81.32(17) . . C2 N3 C4 C5 93.83(16) . . C2 N3 C6 C7 -178.68(13) . . C4 N3 C6 C7 -3.3(2) . . C2 N3 C6 S2 1.05(14) . . C4 N3 C6 S2 176.45(10) . . C1 S2 C6 N3 -0.97(10) . . C1 S2 C6 C7 178.78(11) . . N3 C6 C7 C10 -4.4(2) . . S2 C6 C7 C10 175.85(12) . . N3 C6 C7 C8 175.32(13) . . S2 C6 C7 C8 -4.39(18) . .