Bis-(S-Benzylthiuronium) Chloranilate Supramolecular Crystal Structure: Preparation and Characterization (CM040182M) _publ_contact_author Panayotis G. Veltsistas _publ_contact_author_email panavelt@cc.uoi.gr _publ_author_name Dimitrios V. Stergiou Stavroula Skoulika Nicholaos P. Evmiridis Panayotis G. Veltsistas _journal_name_full Chemistry of Materials _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Cl N2 O2 S' _chemical_formula_weight 270.73 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' 'O' 'O' 0.0106 0.0060 '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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 15.1090(10) _cell_length_b 11.606(2) _cell_length_c 14.390(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.010(10) _cell_angle_gamma 90.00 _cell_volume 2504.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 12.4 _exptl_crystal_description prismatic _exptl_crystal_colour red _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.462 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type P4 _diffrn_measurement_method scintillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2520 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2198 _reflns_number_gt 1635 _reflns_threshold_expression >2sigma(I) _computing_data_collection XSCANS _computing_cell_refinement XSCANS _computing_data_reduction XSCANS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SCHAKAL _computing_publication_material ? _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 fullcycle _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+7.7046P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2198 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.090 _refine_ls_shift/su_mean 0.005 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1015(3) 0.0209(3) 0.3703(2) 0.0442(9) Uani 1 d . . . C2 C -0.0121(3) -0.0069(4) 0.3808(3) 0.0512(10) Uani 1 d . . . C3 C 0.0521(3) 0.0782(4) 0.3819(3) 0.0593(12) Uani 1 d . . . C4 C 0.0268(4) 0.1922(5) 0.3728(3) 0.0658(13) Uani 1 d . . . C5 C -0.0618(4) 0.2200(5) 0.3630(4) 0.0709(14) Uani 1 d . . . C6 C -0.1253(4) 0.1357(4) 0.3608(4) 0.0595(12) Uani 1 d . . . C7 C -0.1704(3) -0.0694(4) 0.3726(3) 0.0496(10) Uani 1 d . . . S7 S -0.24214(7) -0.08941(10) 0.26147(8) 0.0525(3) Uani 1 d . . . C8 C -0.1782(2) -0.1718(3) 0.1940(2) 0.0352(8) Uani 1 d . . . C9 C 0.4164(2) -0.0498(3) 0.5210(2) 0.0331(8) Uani 1 d . . . O9 O 0.34805(16) -0.1020(2) 0.53876(18) 0.0450(7) Uani 1 d . . . C10 C 0.4161(2) 0.0527(3) 0.4704(2) 0.0341(8) Uani 1 d . . . Cl10 Cl 0.31381(6) 0.11633(9) 0.43220(7) 0.0500(3) Uani 1 d . . . C11 C 0.5071(2) -0.1035(3) 0.5567(2) 0.0346(8) Uani 1 d . . . O11 O 0.50707(17) -0.1901(2) 0.60805(18) 0.0447(7) Uani 1 d . . . N1 N -0.1140(2) -0.2377(3) 0.2290(3) 0.0439(8) Uani 1 d . . . N2 N -0.2002(2) -0.1688(3) 0.1024(2) 0.0425(8) Uani 1 d . . . H2 H 0.006(3) -0.083(4) 0.390(3) 0.064(13) Uiso 1 d . . . H3 H 0.117(3) 0.055(4) 0.396(3) 0.076(15) Uiso 1 d . . . H4 H 0.071(3) 0.251(4) 0.373(3) 0.071(15) Uiso 1 d . . . H5 H -0.075(5) 0.295(6) 0.353(5) 0.13(3) Uiso 1 d . . . H6 H -0.177(3) 0.155(5) 0.356(4) 0.074(17) Uiso 1 d . . . H71 H -0.144(2) -0.137(3) 0.397(2) 0.034(10) Uiso 1 d . . . H72 H -0.218(3) -0.048(4) 0.406(3) 0.065(13) Uiso 1 d . . . H11 H -0.079(3) -0.274(4) 0.191(3) 0.065(14) Uiso 1 d . . . H12 H -0.097(3) -0.254(4) 0.282(4) 0.072(17) Uiso 1 d . . . H13 H -0.242(2) -0.126(3) 0.077(2) 0.027(9) Uiso 1 d . . . H14 H -0.176(3) -0.221(4) 0.069(3) 0.063(14) Uiso 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 C1 0.059(2) 0.046(2) 0.0292(18) -0.0054(16) 0.0132(17) 0.0097(19) C2 0.056(3) 0.048(3) 0.050(2) -0.0072(19) 0.0078(19) 0.012(2) C3 0.052(3) 0.066(3) 0.059(3) -0.010(2) 0.002(2) 0.006(2) C4 0.077(4) 0.061(3) 0.060(3) -0.014(2) 0.011(3) -0.018(3) C5 0.088(4) 0.044(3) 0.080(4) -0.012(2) 0.007(3) 0.006(3) C6 0.063(3) 0.048(3) 0.066(3) -0.009(2) 0.004(2) 0.019(2) C7 0.064(3) 0.049(3) 0.040(2) -0.0017(19) 0.023(2) 0.007(2) S7 0.0426(6) 0.0572(7) 0.0589(7) -0.0136(5) 0.0117(5) 0.0113(5) C8 0.0336(18) 0.0303(18) 0.042(2) -0.0031(15) 0.0072(15) -0.0044(15) C9 0.0356(18) 0.0331(19) 0.0311(17) 0.0001(14) 0.0065(14) -0.0052(15) O9 0.0379(14) 0.0450(15) 0.0527(15) 0.0142(12) 0.0078(12) -0.0078(12) C10 0.0308(17) 0.0352(19) 0.0359(18) 0.0048(15) 0.0024(14) -0.0025(14) Cl10 0.0357(5) 0.0504(6) 0.0634(6) 0.0192(5) 0.0048(4) 0.0016(4) C11 0.045(2) 0.0305(18) 0.0286(17) 0.0002(14) 0.0056(15) -0.0040(15) O11 0.0486(15) 0.0394(14) 0.0471(15) 0.0190(12) 0.0107(12) -0.0024(12) N1 0.048(2) 0.046(2) 0.0383(19) 0.0015(16) 0.0089(16) 0.0128(16) N2 0.0437(19) 0.0399(19) 0.0428(19) -0.0052(15) 0.0002(16) 0.0063(16) _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 C1 C2 1.380(9) . ? C1 C6 1.381(9) . ? C1 C7 1.480(9) . ? C2 C3 1.383(10) . ? C2 H2 0.93(7) . ? C3 C4 1.379(11) . ? C3 H3 1.02(8) . ? C4 C5 1.367(12) . ? C4 H4 0.95(8) . ? C5 C6 1.368(11) . ? C5 H5 0.90(11) . ? C6 H6 0.81(8) . ? C7 S7 1.834(7) . ? C7 H71 0.93(6) . ? C7 H72 0.94(7) . ? S7 C8 1.737(5) . ? C8 N1 1.289(7) . ? C8 N2 1.320(7) . ? C9 O9 1.250(6) . ? C9 C10 1.394(7) . ? C9 C11 1.536(7) . ? C10 C11 1.399(7) 5_656 ? C10 Cl10 1.740(5) . ? C11 O11 1.248(6) . ? C11 C10 1.399(7) 5_656 ? N1 H11 0.91(7) . ? N1 H12 0.80(8) . ? N2 H13 0.85(6) . ? N2 H14 0.88(7) . ? 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 C1 C6 118.4(6) . . ? C2 C1 C7 120.9(6) . . ? C6 C1 C7 120.7(6) . . ? C1 C2 C3 120.7(6) . . ? C1 C2 H2 120(5) . . ? C3 C2 H2 119(5) . . ? C4 C3 C2 119.8(7) . . ? C4 C3 H3 122(5) . . ? C2 C3 H3 118(5) . . ? C5 C4 C3 119.6(7) . . ? C5 C4 H4 120(5) . . ? C3 C4 H4 120(5) . . ? C6 C5 C4 120.5(7) . . ? C6 C5 H5 123(8) . . ? C4 C5 H5 116(8) . . ? C5 C6 C1 121.0(7) . . ? C5 C6 H6 118(6) . . ? C1 C6 H6 121(6) . . ? C1 C7 S7 114.4(4) . . ? C1 C7 H71 110(4) . . ? S7 C7 H71 114(3) . . ? C1 C7 H72 114(5) . . ? S7 C7 H72 94(4) . . ? H71 C7 H72 110(6) . . ? C8 S7 C7 104.3(3) . . ? N1 C8 N2 119.5(5) . . ? N1 C8 S7 123.5(4) . . ? N2 C8 S7 117.0(4) . . ? O9 C9 C10 124.8(5) . . ? O9 C9 C11 117.4(4) . . ? C10 C9 C11 117.8(4) . . ? C9 C10 C11 123.7(5) . 5_656 ? C9 C10 Cl10 118.2(4) . . ? C11 C10 Cl10 117.9(4) 5_656 . ? O11 C11 C10 124.4(5) . 5_656 ? O11 C11 C9 117.4(5) . . ? C10 C11 C9 118.2(4) 5_656 . ? C8 N1 H11 120(5) . . ? C8 N1 H12 131(6) . . ? H11 N1 H12 109(7) . . ? C8 N2 H13 122(4) . . ? C8 N2 H14 117(5) . . ? H13 N2 H14 120(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 C6 C1 C2 C3 0.0(9) . . . . ? C7 C1 C2 C3 -177.8(6) . . . . ? C1 C2 C3 C4 0.4(10) . . . . ? C2 C3 C4 C5 0.1(11) . . . . ? C3 C4 C5 C6 -1.0(12) . . . . ? C4 C5 C6 C1 1.4(12) . . . . ? C2 C1 C6 C5 -0.9(10) . . . . ? C7 C1 C6 C5 176.9(6) . . . . ? C2 C1 C7 S7 -114.3(6) . . . . ? C6 C1 C7 S7 68.0(7) . . . . ? C1 C7 S7 C8 79.2(5) . . . . ? C7 S7 C8 N1 24.0(6) . . . . ? C7 S7 C8 N2 -158.9(4) . . . . ? O9 C9 C10 C11 -173.3(5) . . . 5_656 ? C11 C9 C10 C11 6.0(8) . . . 5_656 ? O9 C9 C10 Cl10 2.3(7) . . . . ? C11 C9 C10 Cl10 -178.4(3) . . . . ? O9 C9 C11 O11 -6.1(7) . . . . ? C10 C9 C11 O11 174.5(5) . . . . ? O9 C9 C11 C10 173.7(5) . . . 5_656 ? C10 C9 C11 C10 -5.7(8) . . . 5_656 ? _diffrn_measured_fraction_theta_max 0.474 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.474 _refine_diff_density_max 0.279 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.065