# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Yasushi Morita' _publ_contact_author_address ; 1-1 Machikaneyama, Toyonaka, Osaka, Japan ; _publ_contact_author_email morita@chem.sci.osaka-u.ac.jp _publ_contact_author_fax ' +81-6-6850-5395 ' _publ_contact_author_phone ' +81-6-6850-5393 ' _publ_section_title ; Proton-transfer salts between an EDT-TTF derivative having imidazole-ring and anilic acids: Multi-dimensional networks by acid-base hydrogen-bonds, p-stacks and chalcogen atom interactions ; _publ_requested_category FO loop_ _publ_author_name T.Murata Y.Yakiyama K.Nakasuji Y.Morita #TrackingRef '- CIF.cif' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_edt _database_code_depnum_ccdc_archive 'CCDC 818201' #TrackingRef '- CIF.cif' _audit_creation_date 2011-03-16T19:07:53-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (EDTTTFImH)2(CLA) ; _chemical_formula_moiety 'C11 H9 N2 S6, 0.5(C6 O4 Cl2)' _chemical_formula_sum 'C28 H18 Cl2 N4 O4 S12' _chemical_formula_weight 930.08 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_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' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.3820(14) _cell_length_b 10.5120(4) _cell_length_c 21.654(2) _cell_angle_alpha 90 _cell_angle_beta 108.560(4) _cell_angle_gamma 90 _cell_volume 3535.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.937 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_unetI/netI 0.0269 _diffrn_reflns_number 3373 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_max 0.933 _reflns_number_total 3373 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+4.8136P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3373 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.5 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' Cl Cl 0.1484 0.1585 '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_ _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.35299(5) 1.14705(7) 0.09129(4) 0.05150(19) Uani 1 1 d . . . O1 O -0.20628(12) 1.02307(17) 0.05955(10) 0.0468(5) Uani 1 1 d . . . C13 C -0.18133(15) 1.1783(2) -0.01233(13) 0.0359(5) Uani 1 1 d . . . C14 C -0.29697(16) 1.2024(2) 0.04041(13) 0.0374(6) Uani 1 1 d . . . C12 C -0.23036(15) 1.1281(2) 0.03257(13) 0.0359(5) Uani 1 1 d . . . O2 O -0.12567(11) 1.10734(17) -0.02247(10) 0.0467(5) Uani 1 1 d . . . S4 S 0.08550(4) 0.42367(7) 0.19908(4) 0.04422(18) Uani 1 1 d . . . S3 S -0.06980(4) 0.26710(7) 0.14504(4) 0.0491(2) Uani 1 1 d . . . S2 S -0.03856(4) 0.68251(7) 0.15881(4) 0.04677(19) Uani 1 1 d . . . S1 S -0.18850(4) 0.51269(6) 0.11330(4) 0.04739(19) Uani 1 1 d . . . S6 S 0.20485(5) 0.20158(8) 0.22510(5) 0.0617(2) Uani 1 1 d . . . S5 S 0.02252(6) 0.02403(8) 0.15388(5) 0.0681(3) Uani 1 1 d . . . N2 N -0.36176(13) 0.6432(2) 0.03596(11) 0.0399(5) Uani 1 1 d . . . H2 H -0.3611 0.5482 0.0332 0.048 Uiso 1 1 calc R . . N1 N -0.32011(14) 0.8384(2) 0.05646(11) 0.0409(5) Uani 1 1 d . . . H1 H -0.2829 0.9149 0.072 0.049 Uiso 1 1 calc R . . C1 C -0.29312(16) 0.7172(2) 0.06246(12) 0.0356(5) Uani 1 1 d . . . C4 C -0.20520(16) 0.6747(2) 0.09488(12) 0.0366(5) Uani 1 1 d . . . C8 C 0.02966(16) 0.1881(3) 0.16625(13) 0.0419(6) Uani 1 1 d . . . C3 C -0.40736(17) 0.8397(3) 0.02538(15) 0.0459(7) Uani 1 1 d . . . H4 H -0.4448 0.917 0.014 0.055 Uiso 1 1 calc R . . C6 C -0.07588(16) 0.5252(2) 0.14378(13) 0.0397(6) Uani 1 1 d . . . C2 C -0.43338(16) 0.7190(3) 0.01309(14) 0.0439(6) Uani 1 1 d . . . H3 H -0.4937 0.6895 -0.0087 0.053 Uiso 1 1 calc R . . C5 C -0.13651(17) 0.7512(2) 0.11634(13) 0.0407(6) Uani 1 1 d . . . H5 H -0.1416 0.8449 0.1081 0.049 Uiso 1 1 calc R . . C9 C 0.10024(16) 0.2601(3) 0.19128(13) 0.0422(6) Uani 1 1 d . . . C7 C -0.02576(16) 0.4211(3) 0.15851(13) 0.0389(6) Uani 1 1 d . . . C10 C 0.1261(2) -0.0350(4) 0.2029(2) 0.0784(12) Uani 1 1 d . . . H7A H 0.1169 -0.1161 0.2239 0.094 Uiso 1 1 calc R . . H7B H 0.1602 -0.0561 0.1733 0.094 Uiso 1 1 calc R . . C11 C 0.1787(2) 0.0516(3) 0.25480(18) 0.0644(9) Uani 1 1 d . . . H6B H 0.2335 0.0072 0.2792 0.077 Uiso 1 1 calc R . . H6A H 0.1466 0.0688 0.2862 0.077 Uiso 1 1 calc R . . 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 Cl1 0.0545(4) 0.0404(4) 0.0688(5) 0.0065(3) 0.0327(4) -0.0001(3) O1 0.0403(10) 0.0275(10) 0.0709(14) 0.0122(8) 0.0156(9) 0.0049(7) C13 0.0259(12) 0.0249(13) 0.0544(16) -0.0012(10) 0.0093(11) -0.0006(9) C14 0.0328(13) 0.0267(13) 0.0541(16) 0.0034(10) 0.0159(11) -0.0021(9) C12 0.0299(12) 0.0214(12) 0.0527(16) 0.0013(9) 0.0081(11) -0.0013(9) O2 0.0342(10) 0.0278(10) 0.0817(15) 0.0014(8) 0.0237(9) 0.0028(7) S4 0.0309(3) 0.0387(4) 0.0581(4) 0.0019(3) 0.0072(3) -0.0002(3) S3 0.0304(3) 0.0365(4) 0.0718(5) 0.0019(3) 0.0043(3) 0.0018(3) S2 0.0348(4) 0.0385(4) 0.0585(4) 0.0018(3) 0.0027(3) -0.0029(3) S1 0.0318(3) 0.0295(4) 0.0731(5) 0.0060(3) 0.0057(3) 0.0014(2) S6 0.0301(4) 0.0550(5) 0.0943(7) 0.0080(4) 0.0117(4) 0.0065(3) S5 0.0502(5) 0.0379(5) 0.0994(7) -0.0058(4) 0.0002(4) 0.0050(3) N2 0.0346(11) 0.0276(12) 0.0561(14) 0.0004(9) 0.0127(10) 0.0014(8) N1 0.0369(12) 0.0278(12) 0.0549(14) 0.0020(9) 0.0101(10) 0.0031(8) C1 0.0354(13) 0.0283(13) 0.0435(14) 0.0025(10) 0.0130(11) 0.0027(9) C4 0.0361(13) 0.0311(14) 0.0426(14) 0.0021(10) 0.0127(11) 0.0029(10) C8 0.0337(13) 0.0368(15) 0.0501(16) 0.0026(11) 0.0063(11) 0.0044(10) C3 0.0372(14) 0.0361(16) 0.0624(18) 0.0044(12) 0.0129(13) 0.0090(10) C6 0.0339(13) 0.0361(14) 0.0463(15) 0.0051(11) 0.0087(11) 0.0023(10) C2 0.0284(13) 0.0396(16) 0.0615(18) 0.0019(12) 0.0112(12) 0.0037(10) C5 0.0395(14) 0.0281(14) 0.0519(16) 0.0031(10) 0.0109(12) 0.0015(10) C9 0.0330(13) 0.0418(16) 0.0500(16) 0.0043(11) 0.0106(11) 0.0048(10) C7 0.0328(13) 0.0379(15) 0.0441(15) 0.0036(11) 0.0096(11) 0.0021(10) C10 0.054(2) 0.048(2) 0.118(3) 0.0005(19) 0.007(2) 0.0108(15) C11 0.0508(19) 0.051(2) 0.079(2) 0.0119(16) 0.0040(17) 0.0140(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl1 C14 1.743(3) . ? O1 C12 1.253(3) . ? C13 O2 1.251(3) . ? C13 C14 1.389(3) 7_475 ? C13 C12 1.538(4) . ? C14 C13 1.389(3) 7_475 ? C14 C12 1.396(3) . ? S4 C9 1.752(3) . ? S4 C7 1.754(3) . ? S3 C8 1.755(3) . ? S3 C7 1.758(3) . ? S2 C5 1.733(3) . ? S2 C6 1.757(3) . ? S1 C4 1.751(3) . ? S1 C6 1.755(3) . ? S6 C9 1.747(3) . ? S6 C11 1.806(4) . ? S5 C8 1.744(3) . ? S5 C10 1.801(3) . ? N2 C1 1.338(3) . ? N2 C2 1.374(3) . ? N2 H2 1 . ? N1 C1 1.341(3) . ? N1 C3 1.373(3) . ? N1 H1 1 . ? C1 C4 1.457(3) . ? C4 C5 1.340(4) . ? C8 C9 1.343(4) . ? C3 C2 1.338(4) . ? C3 H4 1 . ? C6 C7 1.344(4) . ? C2 H3 1 . ? C5 H5 1 . ? C10 C11 1.489(5) . ? C10 H7A 1 . ? C10 H7B 1 . ? C11 H6B 1 . ? C11 H6A 1 . ? 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 O2 C13 C14 124.1(2) . 7_475 ? O2 C13 C12 117.6(2) . . ? C14 C13 C12 118.3(2) 7_475 . ? C13 C14 C12 123.6(2) 7_475 . ? C13 C14 Cl1 117.72(19) 7_475 . ? C12 C14 Cl1 118.65(19) . . ? O1 C12 C14 125.4(2) . . ? O1 C12 C13 116.5(2) . . ? C14 C12 C13 118.1(2) . . ? C9 S4 C7 95.14(12) . . ? C8 S3 C7 95.42(13) . . ? C5 S2 C6 94.87(12) . . ? C4 S1 C6 94.71(12) . . ? C9 S6 C11 98.29(14) . . ? C8 S5 C10 104.22(16) . . ? C1 N2 C2 108.8(2) . . ? C1 N2 H2 125.6 . . ? C2 N2 H2 125.6 . . ? C1 N1 C3 108.5(2) . . ? C1 N1 H1 125.8 . . ? C3 N1 H1 125.8 . . ? N2 C1 N1 107.8(2) . . ? N2 C1 C4 126.5(2) . . ? N1 C1 C4 125.7(2) . . ? C5 C4 C1 125.1(2) . . ? C5 C4 S1 116.8(2) . . ? C1 C4 S1 117.83(19) . . ? C9 C8 S5 128.8(2) . . ? C9 C8 S3 116.6(2) . . ? S5 C8 S3 114.63(15) . . ? C2 C3 N1 107.7(2) . . ? C2 C3 H4 126.1 . . ? N1 C3 H4 126.1 . . ? C7 C6 S1 121.2(2) . . ? C7 C6 S2 124.9(2) . . ? S1 C6 S2 113.70(14) . . ? C3 C2 N2 107.3(2) . . ? C3 C2 H3 126.4 . . ? N2 C2 H3 126.4 . . ? C4 C5 S2 117.9(2) . . ? C4 C5 H5 121.1 . . ? S2 C5 H5 121.1 . . ? C8 C9 S6 125.1(2) . . ? C8 C9 S4 117.7(2) . . ? S6 C9 S4 116.86(16) . . ? C6 C7 S4 124.4(2) . . ? C6 C7 S3 121.5(2) . . ? S4 C7 S3 113.80(14) . . ? C11 C10 S5 116.4(3) . . ? C11 C10 H7A 108.2 . . ? S5 C10 H7A 108.2 . . ? C11 C10 H7B 108.2 . . ? S5 C10 H7B 108.2 . . ? H7A C10 H7B 107.3 . . ? C10 C11 S6 114.3(3) . . ? C10 C11 H6B 108.7 . . ? S6 C11 H6B 108.7 . . ? C10 C11 H6A 108.7 . . ? S6 C11 H6A 108.7 . . ? H6B C11 H6A 107.6 . . ? 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 C13 C14 C12 O1 176.4(2) 7_475 . . . ? Cl1 C14 C12 O1 -0.3(4) . . . . ? C13 C14 C12 C13 -3.1(4) 7_475 . . . ? Cl1 C14 C12 C13 -179.84(18) . . . . ? O2 C13 C12 O1 5.1(3) . . . . ? C14 C13 C12 O1 -176.6(2) 7_475 . . . ? O2 C13 C12 C14 -175.3(2) . . . . ? C14 C13 C12 C14 2.9(4) 7_475 . . . ? C2 N2 C1 N1 -0.3(3) . . . . ? C2 N2 C1 C4 177.1(3) . . . . ? C3 N1 C1 N2 -0.2(3) . . . . ? C3 N1 C1 C4 -177.6(2) . . . . ? N2 C1 C4 C5 174.3(3) . . . . ? N1 C1 C4 C5 -8.7(4) . . . . ? N2 C1 C4 S1 -11.1(4) . . . . ? N1 C1 C4 S1 165.8(2) . . . . ? C6 S1 C4 C5 -8.9(2) . . . . ? C6 S1 C4 C1 176.0(2) . . . . ? C10 S5 C8 C9 16.1(3) . . . . ? C10 S5 C8 S3 -161.8(2) . . . . ? C7 S3 C8 C9 7.5(3) . . . . ? C7 S3 C8 S5 -174.38(16) . . . . ? C1 N1 C3 C2 0.6(3) . . . . ? C4 S1 C6 C7 -171.3(2) . . . . ? C4 S1 C6 S2 13.73(17) . . . . ? C5 S2 C6 C7 171.9(3) . . . . ? C5 S2 C6 S1 -13.39(18) . . . . ? N1 C3 C2 N2 -0.7(3) . . . . ? C1 N2 C2 C3 0.6(3) . . . . ? C1 C4 C5 S2 175.5(2) . . . . ? S1 C4 C5 S2 0.9(3) . . . . ? C6 S2 C5 C4 7.7(2) . . . . ? S5 C8 C9 S6 -6.1(4) . . . . ? S3 C8 C9 S6 171.75(16) . . . . ? S5 C8 C9 S4 -178.55(17) . . . . ? S3 C8 C9 S4 -0.7(3) . . . . ? C11 S6 C9 C8 -29.8(3) . . . . ? C11 S6 C9 S4 142.68(19) . . . . ? C7 S4 C9 C8 -6.5(3) . . . . ? C7 S4 C9 S6 -179.55(17) . . . . ? S1 C6 C7 S4 -171.10(15) . . . . ? S2 C6 C7 S4 3.2(4) . . . . ? S1 C6 C7 S3 2.6(3) . . . . ? S2 C6 C7 S3 176.94(15) . . . . ? C9 S4 C7 C6 -174.6(3) . . . . ? C9 S4 C7 S3 11.24(17) . . . . ? C8 S3 C7 C6 174.1(2) . . . . ? C8 S3 C7 S4 -11.57(18) . . . . ? C8 S5 C10 C11 18.4(4) . . . . ? S5 C10 C11 S6 -60.1(4) . . . . ? C9 S6 C11 C10 62.6(3) . . . . ? _chemical_name_common (EDTTTFImH)2(CLA) #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_texray _database_code_depnum_ccdc_archive 'CCDC 818202' #TrackingRef '- CIF.cif' _audit_creation_date 2011-03-16T19:25:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; (EDTTTFImH)2(CNA) ; _chemical_formula_moiety 'C11 H9 N2 S6, C8 N2 O4' _chemical_formula_sum 'C15 H9 N3 O2 S6' _chemical_formula_weight 455.61 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.762(5) _cell_length_b 10.467(8) _cell_length_c 10.572(7) _cell_angle_alpha 92.16(3) _cell_angle_beta 114.66(2) _cell_angle_gamma 112.01(2) _cell_volume 885.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.789 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_unetI/netI 0.0614 _diffrn_reflns_number 8728 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.4 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _reflns_number_total 3992 _reflns_number_gt 3198 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3992 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.488 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.095 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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_ _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.72838(18) 0.45401(17) 0.44786(16) 0.0248(3) Uani 1 1 d . . . O2 O 0.59972(18) 0.62786(16) 0.31580(16) 0.0251(3) Uani 1 1 d . . . C12 C 0.6259(2) 0.4746(2) 0.4762(2) 0.0208(5) Uani 1 1 d . . . C15 C 0.6444(3) 0.3219(2) 0.6454(2) 0.0258(5) Uani 1 1 d . . . N3 N 0.7019(3) 0.2500(2) 0.7069(2) 0.0389(5) Uani 1 1 d . . . C13 C 0.5483(2) 0.5704(2) 0.3980(2) 0.0200(4) Uani 1 1 d . . . C14 C 0.5739(2) 0.4115(2) 0.5742(2) 0.0201(4) Uani 1 1 d . . . S1 S 0.35253(6) 0.25905(6) 0.17515(6) 0.02290(15) Uani 1 1 d . . . S4 S -0.17926(6) 0.10643(6) 0.05357(6) 0.02228(15) Uani 1 1 d . . . S3 S 0.12728(6) 0.19771(6) 0.32950(6) 0.02538(15) Uani 1 1 d . . . S2 S 0.06145(6) 0.18183(6) -0.10965(6) 0.02372(15) Uani 1 1 d . . . S6 S -0.40788(7) 0.04813(7) 0.18078(6) 0.03269(17) Uani 1 1 d . . . S5 S -0.04197(7) 0.16697(8) 0.50985(6) 0.03529(18) Uani 1 1 d . . . C7 C 0.0396(2) 0.1769(2) 0.1433(2) 0.0186(4) Uani 1 1 d . . . C6 C 0.1357(2) 0.2047(2) 0.0766(2) 0.0195(4) Uani 1 1 d . . . C3 C 0.5649(3) 0.3599(2) 0.0566(2) 0.0197(4) Uani 1 1 d . . . N2 N 0.7010(2) 0.42041(19) 0.1840(2) 0.0229(4) Uani 1 1 d . . . H2 H 0.7007 0.4314 0.2783 0.027 Uiso 1 1 calc R . . C5 C 0.2577(3) 0.2585(2) -0.0997(2) 0.0224(5) Uani 1 1 d . . . H5 H 0.2712 0.2738 -0.1874 0.027 Uiso 1 1 calc R . . C9 C -0.2015(3) 0.1096(2) 0.2110(2) 0.0214(5) Uani 1 1 d . . . C4 C 0.3923(2) 0.2972(2) 0.0303(2) 0.0202(4) Uani 1 1 d . . . C8 C -0.0611(3) 0.1532(2) 0.3372(2) 0.0232(5) Uani 1 1 d . . . C11 C -0.3828(3) 0.0843(3) 0.3592(3) 0.0285(5) Uani 1 1 d . . . H7A H -0.3502 0.1874 0.3897 0.034 Uiso 1 1 calc R . . H7B H -0.4924 0.03 0.358 0.034 Uiso 1 1 calc R . . C10 C -0.2524(3) 0.0456(3) 0.4679(2) 0.0288(5) Uani 1 1 d . . . H6A H -0.2734 -0.0523 0.4293 0.035 Uiso 1 1 calc R . . H6B H -0.2638 0.0454 0.5576 0.035 Uiso 1 1 calc R . . C2 C 0.8417(3) 0.4653(2) 0.1647(3) 0.0277(5) Uani 1 1 d . . . H4 H 0.9603 0.5138 0.2413 0.033 Uiso 1 1 calc R . . C1 C 0.7887(3) 0.4313(3) 0.0232(2) 0.0282(5) Uani 1 1 d . . . H3 H 0.8611 0.4498 -0.0249 0.034 Uiso 1 1 calc R . . N1 N 0.6163(2) 0.3661(2) -0.0436(2) 0.0256(4) Uani 1 1 d . . . H1 H 0.5421 0.3296 -0.149 0.031 Uiso 1 1 calc R . . 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 O1 0.0216(8) 0.0358(9) 0.0215(8) 0.0069(7) 0.0137(7) 0.0125(7) O2 0.0250(8) 0.0341(9) 0.0207(8) 0.0104(7) 0.0157(7) 0.0109(7) C12 0.0166(10) 0.0258(12) 0.0152(11) 0.0015(9) 0.0078(9) 0.0042(9) C15 0.0285(12) 0.0338(13) 0.0224(12) 0.0068(10) 0.0180(10) 0.0134(10) N3 0.0483(13) 0.0496(14) 0.0343(13) 0.0179(11) 0.0239(11) 0.0301(12) C13 0.0176(10) 0.0255(11) 0.0102(10) 0.0016(8) 0.0052(8) 0.0045(9) C14 0.0187(10) 0.0268(12) 0.0146(11) 0.0063(9) 0.0083(9) 0.0088(9) S1 0.0153(3) 0.0342(3) 0.0153(3) 0.0046(2) 0.0085(2) 0.0054(2) S4 0.0154(3) 0.0314(3) 0.0170(3) 0.0049(2) 0.0076(2) 0.0071(2) S3 0.0152(3) 0.0373(4) 0.0166(3) 0.0027(2) 0.0067(2) 0.0055(2) S2 0.0182(3) 0.0313(3) 0.0166(3) 0.0065(2) 0.0071(2) 0.0068(2) S6 0.0169(3) 0.0570(4) 0.0210(3) 0.0070(3) 0.0097(2) 0.0120(3) S5 0.0241(3) 0.0580(4) 0.0180(3) 0.0059(3) 0.0110(2) 0.0108(3) C7 0.0152(9) 0.0211(11) 0.0153(11) 0.0029(8) 0.0059(8) 0.0050(8) C6 0.0163(10) 0.0203(11) 0.0175(11) 0.0035(9) 0.0070(9) 0.0045(8) C3 0.0214(10) 0.0207(11) 0.0178(11) 0.0068(9) 0.0111(9) 0.0075(9) N2 0.0207(9) 0.0268(10) 0.0213(10) 0.0047(8) 0.0129(8) 0.0069(8) C5 0.0221(10) 0.0287(12) 0.0177(11) 0.0092(9) 0.0113(9) 0.0097(9) C9 0.0184(10) 0.0288(12) 0.0165(11) 0.0067(9) 0.0085(9) 0.0089(9) C4 0.0196(10) 0.0225(11) 0.0210(12) 0.0061(9) 0.0130(9) 0.0073(9) C8 0.0197(10) 0.0310(12) 0.0202(12) 0.0065(10) 0.0124(9) 0.0087(9) C11 0.0274(11) 0.0381(14) 0.0276(13) 0.0118(11) 0.0187(11) 0.0144(11) C10 0.0253(11) 0.0412(14) 0.0229(13) 0.0126(11) 0.0141(10) 0.0136(11) C2 0.0193(10) 0.0310(13) 0.0335(14) 0.0047(10) 0.0159(10) 0.0077(10) C1 0.0218(11) 0.0378(14) 0.0272(13) 0.0049(10) 0.0161(10) 0.0099(10) N1 0.0236(9) 0.0306(11) 0.0237(10) 0.0031(8) 0.0158(8) 0.0077(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C12 1.243(2) . ? O2 C13 1.243(2) . ? C12 C14 1.416(3) . ? C12 C13 1.540(3) . ? C15 N3 1.163(3) . ? C15 C14 1.423(3) . ? C13 C14 1.415(3) 2_666 ? C14 C13 1.415(3) 2_666 ? S1 C4 1.755(2) . ? S1 C6 1.761(2) . ? S4 C7 1.756(2) . ? S4 C9 1.766(2) . ? S3 C7 1.754(2) . ? S3 C8 1.758(2) . ? S2 C5 1.732(2) . ? S2 C6 1.762(2) . ? S6 C9 1.747(2) . ? S6 C11 1.804(3) . ? S5 C8 1.750(2) . ? S5 C10 1.809(2) . ? C7 C6 1.351(3) . ? C3 N2 1.339(3) . ? C3 N1 1.342(3) . ? C3 C4 1.455(3) . ? N2 C2 1.381(3) . ? N2 H2 1 . ? C5 C4 1.353(3) . ? C5 H5 1 . ? C9 C8 1.352(3) . ? C11 C10 1.519(3) . ? C11 H7A 1 . ? C11 H7B 1 . ? C10 H6A 1 . ? C10 H6B 1 . ? C2 C1 1.344(3) . ? C2 H4 1 . ? C1 N1 1.382(3) . ? C1 H3 1 . ? N1 H1 1 . ? 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 O1 C12 C14 123.2(2) . . ? O1 C12 C13 118.33(18) . . ? C14 C12 C13 118.46(18) . . ? N3 C15 C14 178.1(2) . . ? O2 C13 C14 124.7(2) . 2_666 ? O2 C13 C12 117.13(18) . . ? C14 C13 C12 118.13(17) 2_666 . ? C13 C14 C12 123.40(19) 2_666 . ? C13 C14 C15 118.13(18) 2_666 . ? C12 C14 C15 118.44(18) . . ? C4 S1 C6 94.71(10) . . ? C7 S4 C9 95.04(10) . . ? C7 S3 C8 95.57(10) . . ? C5 S2 C6 95.03(10) . . ? C9 S6 C11 102.37(11) . . ? C8 S5 C10 99.33(11) . . ? C6 C7 S3 121.16(17) . . ? C6 C7 S4 123.94(17) . . ? S3 C7 S4 114.75(11) . . ? C7 C6 S2 125.27(17) . . ? C7 C6 S1 120.42(17) . . ? S2 C6 S1 114.21(11) . . ? N2 C3 N1 107.63(18) . . ? N2 C3 C4 126.56(19) . . ? N1 C3 C4 125.8(2) . . ? C3 N2 C2 109.21(18) . . ? C3 N2 H2 125.4 . . ? C2 N2 H2 125.4 . . ? C4 C5 S2 118.03(17) . . ? C4 C5 H5 121 . . ? S2 C5 H5 121 . . ? C8 C9 S6 128.32(17) . . ? C8 C9 S4 117.36(16) . . ? S6 C9 S4 114.27(12) . . ? C5 C4 C3 124.88(19) . . ? C5 C4 S1 116.76(16) . . ? C3 C4 S1 118.27(16) . . ? C9 C8 S5 128.25(17) . . ? C9 C8 S3 116.81(17) . . ? S5 C8 S3 114.91(12) . . ? C10 C11 S6 113.10(15) . . ? C10 C11 H7A 109 . . ? S6 C11 H7A 109 . . ? C10 C11 H7B 109 . . ? S6 C11 H7B 109 . . ? H7A C11 H7B 107.8 . . ? C11 C10 S5 112.40(17) . . ? C11 C10 H6A 109.1 . . ? S5 C10 H6A 109.1 . . ? C11 C10 H6B 109.1 . . ? S5 C10 H6B 109.1 . . ? H6A C10 H6B 107.9 . . ? C1 C2 N2 106.89(19) . . ? C1 C2 H4 126.6 . . ? N2 C2 H4 126.6 . . ? C2 C1 N1 107.60(19) . . ? C2 C1 H3 126.2 . . ? N1 C1 H3 126.2 . . ? C3 N1 C1 108.67(19) . . ? C3 N1 H1 125.7 . . ? C1 N1 H1 125.7 . . ? 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 O1 C12 C13 O2 -3.7(3) . . . . ? C14 C12 C13 O2 177.9(2) . . . . ? O1 C12 C13 C14 177.20(19) . . . 2_666 ? C14 C12 C13 C14 -1.2(3) . . . 2_666 ? O1 C12 C14 C13 -177.1(2) . . . 2_666 ? C13 C12 C14 C13 1.3(3) . . . 2_666 ? O1 C12 C14 C15 1.1(3) . . . . ? C13 C12 C14 C15 179.38(18) . . . . ? C8 S3 C7 C6 177.38(19) . . . . ? C8 S3 C7 S4 -6.98(14) . . . . ? C9 S4 C7 C6 -178.2(2) . . . . ? C9 S4 C7 S3 6.32(14) . . . . ? S3 C7 C6 S2 177.59(12) . . . . ? S4 C7 C6 S2 2.4(3) . . . . ? S3 C7 C6 S1 1.5(3) . . . . ? S4 C7 C6 S1 -173.76(11) . . . . ? C5 S2 C6 C7 173.4(2) . . . . ? C5 S2 C6 S1 -10.29(13) . . . . ? C4 S1 C6 C7 -172.31(19) . . . . ? C4 S1 C6 S2 11.17(13) . . . . ? N1 C3 N2 C2 -0.4(2) . . . . ? C4 C3 N2 C2 179.1(2) . . . . ? C6 S2 C5 C4 4.93(19) . . . . ? C11 S6 C9 C8 8.8(3) . . . . ? C11 S6 C9 S4 -173.85(12) . . . . ? C7 S4 C9 C8 -2.9(2) . . . . ? C7 S4 C9 S6 179.39(12) . . . . ? S2 C5 C4 C3 178.62(16) . . . . ? S2 C5 C4 S1 2.2(2) . . . . ? N2 C3 C4 C5 168.3(2) . . . . ? N1 C3 C4 C5 -12.4(3) . . . . ? N2 C3 C4 S1 -15.4(3) . . . . ? N1 C3 C4 S1 163.92(17) . . . . ? C6 S1 C4 C5 -8.12(19) . . . . ? C6 S1 C4 C3 175.26(16) . . . . ? S6 C9 C8 S5 -2.2(4) . . . . ? S4 C9 C8 S5 -179.55(13) . . . . ? S6 C9 C8 S3 175.80(13) . . . . ? S4 C9 C8 S3 -1.5(3) . . . . ? C10 S5 C8 C9 21.7(2) . . . . ? C10 S5 C8 S3 -156.37(14) . . . . ? C7 S3 C8 C9 5.1(2) . . . . ? C7 S3 C8 S5 -176.59(13) . . . . ? C9 S6 C11 C10 -43.3(2) . . . . ? S6 C11 C10 S5 72.5(2) . . . . ? C8 S5 C10 C11 -55.81(18) . . . . ? C3 N2 C2 C1 0.2(3) . . . . ? N2 C2 C1 N1 0.1(3) . . . . ? N2 C3 N1 C1 0.4(2) . . . . ? C4 C3 N1 C1 -179.0(2) . . . . ? C2 C1 N1 C3 -0.3(3) . . . . ? #==END _chemical_name_common (EDTTTFImH)2(CNA)