# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1145 _publ_requested_journal 'Journal of Materials Chemistry' loop_ _publ_author_name 'Khasanov, Salvat S.' 'Nishimura, Kazukuni' 'Saito, Gunzi' _publ_contact_author_name 'Mr Kazukuni Nishimura' _publ_contact_author_address ; Division of Chemistry Graduate School of Science, Kyoto University Oiwakecho, Sakyo-ku Kyoto city 606-8502 JAPAN ; _publ_contact_author_email 'NISHIMURA@KUCHEM.KYOTO-U.AC.JP' _publ_section_title ; Charge transfer, proton transfer and clathrate compounds of dihydro-tetracyanodiphenoquinodimethane (H2TCNDQ) having highly acidic protons. ; _publ_section_abstract ; We present the crystal and molecular structure of H2TCNDQ. ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using Crystan (MacScience, Japan). ; data_H2TCNDQ _database_code_CSD 172685 _audit_creation_method SHELXL-97 _chemical_name_systematic ; dihydro-tetracyanoquinodiphenoquinodimethane ; _chemical_name_common 'H2TCNDQ' _chemical_melting_point '180 degree C' _chemical_formula_moiety 'C18 H10 N4' _chemical_formula_sum 'C18 H10 N4' _chemical_formula_weight 282.30 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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'C2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 25.255(5) _cell_length_b 7.0840(12) _cell_length_c 8.2600(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.639(13) _cell_angle_gamma 90.00 _cell_volume 1461.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 33 _cell_measurement_theta_min 0 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'plate' _exptl_crystal_colour 'pale-purple' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Mac Science DIP-2020K' _diffrn_measurement_method 'theta/2theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1441 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1441 _reflns_number_gt 969 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.7764P] 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 'refall (H5) / noref (other hydrogen atoms)' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1441 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 N1 N 0.35200(10) 0.2898(4) -0.4820(3) 0.0990(8) Uani 1 1 d . . . N2 N 0.25669(10) 0.0622(5) -0.1442(3) 0.1201(10) Uani 1 1 d . . . C3 C 0.34401(9) 0.2898(4) -0.3497(3) 0.0740(7) Uani 1 1 d . . . C4 C 0.29061(9) 0.1605(4) -0.1605(3) 0.0805(7) Uani 1 1 d . . . C5 C 0.33423(8) 0.2920(3) -0.1784(3) 0.0664(6) Uani 1 1 d . . . H5 H 0.3208(10) 0.418(4) -0.157(3) 0.088(8) Uiso 1 1 d . . . C6 C 0.38465(8) 0.2558(3) -0.0537(3) 0.0604(6) Uani 1 1 d . . . C7 C 0.43494(9) 0.2804(4) -0.0958(3) 0.0767(7) Uani 1 1 d . . . H7 H 0.4389 0.3083 -0.2071 0.103(9) Uiso 1 1 calc R . . C8 C 0.47989(8) 0.2649(4) 0.0231(3) 0.0772(7) Uani 1 1 d . . . H8 H 0.5147 0.2823 -0.0080 0.097(8) Uiso 1 1 calc R . . C9 C 0.47603(8) 0.2252(3) 0.1850(3) 0.0597(5) Uani 1 1 d . . . C10 C 0.42495(8) 0.1963(3) 0.2240(3) 0.0732(7) Uani 1 1 d . . . H10 H 0.4208 0.1648 0.3345 0.091(8) Uiso 1 1 calc R . . C11 C 0.38002(8) 0.2122(3) 0.1062(3) 0.0735(7) Uani 1 1 d . . . H11 H 0.3452 0.1926 0.1363 0.101(8) 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 N1 0.0934(17) 0.114(2) 0.0868(16) 0.0086(15) 0.0038(13) 0.0053(13) N2 0.0703(15) 0.155(3) 0.124(2) 0.0096(18) -0.0200(13) -0.0388(16) C3 0.0595(14) 0.0753(16) 0.0813(17) 0.0022(13) -0.0093(12) 0.0024(11) C4 0.0494(13) 0.1020(19) 0.0822(16) -0.0012(14) -0.0157(11) -0.0086(13) C5 0.0488(12) 0.0691(15) 0.0752(15) -0.0055(11) -0.0102(10) 0.0025(10) C6 0.0438(11) 0.0591(11) 0.0737(14) -0.0033(10) -0.0066(9) -0.0003(8) C7 0.0479(12) 0.108(2) 0.0709(15) -0.0039(13) -0.0006(10) -0.0036(11) C8 0.0412(11) 0.109(2) 0.0789(15) -0.0049(14) 0.0019(10) -0.0044(11) C9 0.0423(11) 0.0572(12) 0.0761(14) -0.0005(10) -0.0025(9) -0.0001(8) C10 0.0457(12) 0.0908(17) 0.0790(16) 0.0161(13) -0.0036(10) -0.0050(11) C11 0.0414(11) 0.0886(17) 0.0870(16) 0.0143(13) -0.0021(10) -0.0058(10) _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 N1 C3 1.141(3) . ? N2 C4 1.128(3) . ? C3 C5 1.473(4) . ? C4 C5 1.467(3) . ? C5 C6 1.535(3) . ? C5 H5 0.98(3) . ? C6 C7 1.377(3) . ? C6 C11 1.378(3) . ? C7 C8 1.389(3) . ? C7 H7 0.9600 . ? C8 C9 1.384(3) . ? C8 H8 0.9600 . ? C9 C10 1.391(3) . ? C9 C9 1.493(4) 2_655 ? C10 C11 1.384(3) . ? C10 H10 0.9600 . ? C11 H11 0.9600 . ? 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 N1 C3 C5 179.2(3) . . ? N2 C4 C5 178.4(3) . . ? C4 C5 C3 109.09(19) . . ? C4 C5 C6 112.69(19) . . ? C3 C5 C6 113.68(19) . . ? C4 C5 H5 105.9(14) . . ? C3 C5 H5 107.4(14) . . ? C6 C5 H5 107.6(14) . . ? C7 C6 C11 118.98(19) . . ? C7 C6 C5 120.8(2) . . ? C11 C6 C5 119.98(19) . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 122.0(2) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 117.15(19) . . ? C8 C9 C9 121.8(2) . 2_655 ? C10 C9 C9 120.9(3) . 2_655 ? C11 C10 C9 121.1(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C6 C11 C10 120.9(2) . . ? C6 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.114 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.035 #===END data_(BO)(H2TCNDQ) _database_code_CSD 172686 _publ_section_exptl_refinement ? _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_structure_solution 'SIR92' _computing_structure_refinement 'Crystan 6.3' _computing_molecular_graphics 'ORTEP III' _computing_publication_material ? _chemical_formula_sum 'C28 H18 N4 O4 S4' _chemical_formula_moiety 'C10 H8 O4 S4, C18 H10 N4' _chemical_formula_weight 602.74 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z _symmetry_space_group_name_H-M 'P-1' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_Hall '-P 1' _cell_length_a 5.4345(7) _cell_length_b 8.718(1) _cell_length_c 14.358(1) _cell_angle_alpha 79.531(8) _cell_angle_beta 88.090(9) _cell_angle_gamma 84.89(1) _cell_volume 666.2(1) _cell_formula_units_Z 1 _exptl_crystal_density_diffrn 1.502 _diffrn_radiation_type 'Mo K-alpha' _diffrn_radiation_wavelength 0.71073 _cell_measurement_reflns_used '21' _cell_measurement_theta_min '0' _cell_measurement_theta_max '55' _diffrn_ambient_temperature 'Room Temterature' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 0.384 _exptl_crystal_description 'plate' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _diffrn_measurement_device_type 'Mac Science MXCchi' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_radiation_monochromator 'Graphite' _diffrn_reflns_number 3347 _reflns_number_total 2816 _reflns_number_gt 2816 _reflns_observed_criterion 'refl_observed_if_I_>_2.00_sigma(I)' _refine_ls_extinction_method 'None' _diffrn_reflns_theta_max 27.50 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.038 _refine_ls_wR_factor_obs 0.038 _refine_ls_goodness_of_fit_obs 0.488 _refine_ls_number_reflns 2391 _refine_ls_number_parameters 217 _refine_ls_shift/su_max 0.1289 _refine_ls_shift/su_mean 0.0076 _refine_ls_weighting_scheme 'Unit' _refine_ls_hydrogen_treatment 'refall' _refine_diff_density_min -0.25 _refine_diff_density_max 0.28 _atoms_sites_solution_primary 'direct method' _atoms_sites_solution_secondary 'Fourier difference' _atom_sites_solution_hydrogens 'Fourier difference' _atom_type_scat_source 'International Tables (1974)' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 -0.16918 _diffrn_orient_matrix_UB_12 0.04279 _diffrn_orient_matrix_UB_13 0.01687 _diffrn_orient_matrix_UB_21 0.04075 _diffrn_orient_matrix_UB_22 -0.02781 _diffrn_orient_matrix_UB_23 0.06874 _diffrn_orient_matrix_UB_31 0.06213 _diffrn_orient_matrix_UB_32 0.10536 _diffrn_orient_matrix_UB_33 -0.00284 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type C1 0.0964(6) -0.0124(4) 0.6595(2) 0.062(2) 1.000 Uij C2 0.3596(7) -0.0581(4) 0.6337(2) 0.066(2) 1.000 Uij C3 0.2561(5) 0.0367(3) 0.7962(2) 0.045(1) 1.000 Uij C4 0.4366(5) -0.0738(3) 0.7919(2) 0.046(1) 1.000 Uij C5 0.4690(4) -0.0031(3) 0.9562(2) 0.040(1) 1.000 Uij C10 0.6551(5) 0.3969(3) 0.6355(2) 0.048(1) 1.000 Uij C11 0.8920(4) 0.4506(3) 0.6565(2) 0.037(1) 1.000 Uij C12 0.9339(5) 0.5956(3) 0.5903(2) 0.050(1) 1.000 Uij C13 0.9135(4) 0.4696(3) 0.7599(1) 0.034(1) 1.000 Uij C14 0.7559(4) 0.4034(3) 0.8299(2) 0.041(1) 1.000 Uij C15 0.7895(4) 0.4154(3) 0.9233(2) 0.041(1) 1.000 Uij C16 0.9805(4) 0.4942(2) 0.9498(1) 0.0312(9) 1.000 Uij C17 1.1351(4) 0.5618(3) 0.8774(2) 0.039(1) 1.000 Uij C18 1.1027(5) 0.5500(3) 0.7841(2) 0.040(1) 1.000 Uij H1A 0.003(5) -0.112(3) 0.690(2) 0.061(8) 1.000 Uiso H1B 0.010(6) 0.043(4) 0.605(2) 0.08(1) 1.000 Uiso H2A 0.462(5) 0.037(4) 0.608(2) 0.068(9) 1.000 Uiso H2B 0.367(6) -0.121(4) 0.588(2) 0.07(1) 1.000 Uiso H11 1.010(5) 0.376(3) 0.643(2) 0.041(7) 1.000 Uiso H14 0.630(5) 0.349(3) 0.815(2) 0.047(7) 1.000 Uiso H15 0.680(5) 0.372(3) 0.969(2) 0.043(7) 1.000 Uiso H17 1.268(4) 0.613(3) 0.891(2) 0.041(7) 1.000 Uiso H18 1.213(4) 0.591(3) 0.736(2) 0.041(7) 1.000 Uiso N19 0.4730(5) 0.3557(4) 0.6190(2) 0.077(2) 1.000 Uij N20 0.9708(6) 0.7073(3) 0.5400(2) 0.077(2) 1.000 Uij O6 0.0883(4) 0.0928(2) 0.7267(1) 0.055(1) 1.000 Uij O7 0.4897(4) -0.1466(2) 0.7157(1) 0.059(1) 1.000 Uij S8 0.22070(13) 0.11750(8) 0.89920(5) 0.0506(3) 1.000 Uij S9 0.63100(12) -0.13200(8) 0.88900(5) 0.0489(3) 1.000 Uij loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.077(2) 0.055(2) 0.051(2) -0.006(2) -0.017(2) -0.007(1) C2 0.085(2) 0.067(2) 0.044(2) -0.019(2) 0.002(2) -0.013(1) C3 0.051(1) 0.043(1) 0.040(1) -0.006(1) -0.005(1) -0.003(1) C4 0.048(1) 0.044(1) 0.045(1) -0.005(1) 0.001(1) -0.009(1) C5 0.039(1) 0.033(1) 0.047(1) 0.001(1) -0.002(1) -0.005(1) C10 0.045(1) 0.064(2) 0.034(1) -0.011(1) -0.001(1) -0.011(1) C11 0.038(1) 0.043(1) 0.031(1) -0.005(1) -0.001(1) -0.009(1) C12 0.064(2) 0.055(2) 0.029(1) -0.014(1) -0.006(1) -0.009(1) C13 0.034(1) 0.037(1) 0.028(1) 0.000(1) -0.002(1) -0.007(1) C14 0.033(1) 0.054(1) 0.035(1) -0.011(1) -0.001(1) -0.009(1) C15 0.034(1) 0.055(1) 0.032(1) -0.010(1) 0.004(1) -0.007(1) C16 0.031(1) 0.031(1) 0.030(1) 0.003(1) 0.000(1) -0.006(1) C17 0.040(1) 0.042(1) 0.035(1) -0.012(1) -0.001(1) -0.009(1) C18 0.043(1) 0.044(1) 0.031(1) -0.012(1) 0.003(1) -0.004(1) N19 0.055(2) 0.116(2) 0.060(2) -0.031(2) -0.002(1) -0.023(2) N20 0.127(3) 0.065(2) 0.038(1) -0.035(2) -0.012(1) -0.001(1) O6 0.066(1) 0.049(1) 0.048(1) 0.002(1) -0.017(1) -0.004(1) O7 0.064(1) 0.063(1) 0.049(1) -0.002(1) 0.002(1) -0.019(1) S8 0.0527(4) 0.0452(4) 0.0512(4) 0.0116(3) -.0115(3) -.0111(3) S9 0.0443(4) 0.0471(4) 0.0534(4) 0.0057(3) -.0044(3) -.0140(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.503(6) . . yes C1 O6 1.444(4) . . yes C2 O7 1.452(4) . . yes C3 C4 1.320(4) . . yes C3 O6 1.368(4) . . yes C3 S8 1.748(3) . . yes C4 O7 1.372(4) . . yes C4 S9 1.750(3) . . yes C5 C5 1.325(4) . 2_657 yes C5 S8 1.762(3) . . yes C5 S9 1.769(3) . . yes C10 C11 1.467(4) . . yes C10 N19 1.129(4) . . yes C11 C12 1.467(4) . . yes C11 C13 1.533(3) . . yes C12 N20 1.131(4) . . yes C13 C14 1.377(4) . . yes C13 C18 1.382(4) . . yes C14 C15 1.383(4) . . yes C15 C16 1.394(4) . . yes C16 C16 1.487(3) . 2_767 yes C16 C17 1.393(4) . . yes C17 C18 1.380(4) . . yes C1 H1A 1.06(3) . . yes C1 H1B 0.95(4) . . yes C2 H2A 1.04(4) . . yes C2 H2B 0.93(4) . . yes C11 H11 0.92(3) . . yes C14 H14 0.92(3) . . yes C15 H15 0.93(3) . . yes C17 H17 0.92(3) . . yes C18 H18 0.94(3) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 O6 110.3(3) . . . yes C1 C2 O7 110.8(3) . . . yes C4 C3 O6 125.3(3) . . . yes C4 C3 S8 118.4(2) . . . yes O6 C3 S8 116.2(2) . . . yes C3 C4 O7 125.2(3) . . . yes C3 C4 S9 118.7(2) . . . yes O7 C4 S9 116.1(2) . . . yes C5 C5 S8 122.0(2) 2_657 . . yes C5 C5 S9 122.2(2) 2_657 . . yes S8 C5 S9 115.9(2) . . . yes C11 C10 N19 179.8(3) . . . yes C10 C11 C12 109.1(3) . . . yes C10 C11 C13 113.6(2) . . . yes C12 C11 C13 111.9(2) . . . yes C11 C12 N20 178.6(4) . . . yes C11 C13 C14 121.8(2) . . . yes C11 C13 C18 119.0(2) . . . yes C14 C13 C18 119.1(2) . . . yes C13 C14 C15 120.3(3) . . . yes C14 C15 C16 121.8(3) . . . yes C15 C16 C16 122.1(2) . . 2_767 yes C15 C16 C17 116.7(2) . . . yes C16 C16 C17 121.2(2) 2_767 . . yes C16 C17 C18 121.7(3) . . . yes C13 C18 C17 120.4(3) . . . yes C1 O6 C3 109.5(3) . . . yes C2 O7 C4 109.1(3) . . . yes C3 S8 C5 93.7(2) . . . yes C4 S9 C5 93.3(2) . . . yes C2 C1 H1A 111.2(16) . . . yes C2 C1 H1B 110.8(21) . . . yes H1A C1 H1B 109.4(25) . . . yes H1A C1 O6 108.8(16) . . . yes H1B C1 O6 106.2(21) . . . yes C1 C2 H2A 113.7(17) . . . yes C1 C2 H2B 111.0(20) . . . yes H2A C2 H2B 107.6(26) . . . yes H2A C2 O7 106.2(17) . . . yes H2B C2 O7 107.3(20) . . . yes C10 C11 H11 105.5(16) . . . yes C12 C11 H11 106.7(16) . . . yes C13 C11 H11 109.7(16) . . . yes C13 C14 H14 120.5(16) . . . yes C15 C14 H14 119.2(16) . . . yes C14 C15 H15 119.0(16) . . . yes C16 C15 H15 119.2(16) . . . yes C16 C17 H17 120.7(15) . . . yes C18 C17 H17 117.5(16) . . . yes C13 C18 H18 118.3(15) . . . yes C17 C18 H18 121.3(15) . . . yes #===END data_(EOET)(H2TCNDQ) _database_code_CSD 172687 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(EOET)(H2TCNDQ)' _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 O2 S6, C18 H10 N4' _chemical_formula_sum 'C28 H18 N4 O2 S6' _chemical_formula_weight 634.82 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4850(5) _cell_length_b 9.0560(10) _cell_length_c 14.4370(16) _cell_angle_alpha 80.614(6) _cell_angle_beta 87.995(6) _cell_angle_gamma 84.202(6) _cell_volume 703.77(13) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 0 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'Plate' _exptl_crystal_colour 'Red' _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 0.521 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Mac Science DIP-2020K' _diffrn_measurement_method 'theta/2theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2668 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 26.49 _reflns_number_total 2668 _reflns_number_gt 2188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.5323P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2668 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1527 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 S1 S -0.13379(19) 0.13551(11) 0.60752(8) 0.0885(4) Uani 1 1 d . . . S2 S 0.26840(19) -0.11001(11) 0.60358(8) 0.0852(3) Uani 1 1 d . . . S3 S -0.0304(3) 0.1798(2) 0.78717(10) 0.0953(5) Uani 0.50 1 d P . . O3 O -0.0304(3) 0.1798(2) 0.78717(10) 0.0953(5) Uani 0.50 1 d P . . S4 S 0.4344(3) -0.08441(19) 0.77987(11) 0.0992(5) Uani 0.50 1 d P . . O4 O 0.4344(3) -0.08441(19) 0.77987(11) 0.0992(5) Uani 0.50 1 d P . . C5 C 0.1132(12) 0.0663(7) 0.8769(3) 0.1214(18) Uani 1 1 d . . . H5A H 0.1059 0.1186 0.9298 0.146 Uiso 1 1 calc R . . H5B H 0.0236 -0.0202 0.8940 0.146 Uiso 1 1 calc R . . C6 C 0.3708(12) 0.0136(6) 0.8599(4) 0.128(2) Uani 1 1 d . . . H6A H 0.4325 -0.0439 0.9176 0.154 Uiso 1 1 calc R . . H6B H 0.4605 0.1005 0.8463 0.154 Uiso 1 1 calc R . . C7 C 0.0528(7) 0.0854(4) 0.7051(3) 0.0759(9) Uani 1 1 d . . . C8 C 0.2341(7) -0.0231(4) 0.7030(3) 0.0739(9) Uani 1 1 d . . . C9 C 0.0278(6) 0.0054(4) 0.5438(3) 0.0706(8) Uani 1 1 d . . . N10 N 1.0237(6) 0.6433(6) 0.8785(2) 0.1181(15) Uani 1 1 d . . . N11 N 0.5285(9) 0.3107(5) 0.9575(2) 0.1100(13) Uani 1 1 d . . . C12 C 0.8438(7) 0.6035(5) 0.8622(2) 0.0815(11) Uani 1 1 d . . . C13 C 0.6082(6) 0.5519(4) 0.84158(19) 0.0646(8) Uani 1 1 d . . . H13 H 0.4822 0.6282 0.8539 0.078 Uiso 1 1 calc R . . C14 C 0.5653(7) 0.4151(5) 0.9068(2) 0.0785(10) Uani 1 1 d . . . C15 C 0.5858(5) 0.5333(3) 0.73855(18) 0.0560(7) Uani 1 1 d . . . C16 C 0.7380(6) 0.5980(4) 0.6691(2) 0.0639(8) Uani 1 1 d . . . H16 H 0.8683 0.6521 0.6851 0.077 Uiso 1 1 calc R . . C17 C 0.7033(5) 0.5853(4) 0.57617(19) 0.0608(7) Uani 1 1 d . . . H17 H 0.8097 0.6320 0.5284 0.073 Uiso 1 1 calc R . . C18 C 0.5184(5) 0.5066(3) 0.55024(16) 0.0468(6) Uani 1 1 d . . . C19 C 0.3705(6) 0.4409(4) 0.62146(19) 0.0609(7) Uani 1 1 d . . . H19 H 0.2421 0.3849 0.6062 0.073 Uiso 1 1 calc R . . C20 C 0.4032(6) 0.4538(4) 0.71449(19) 0.0671(8) Uani 1 1 d . . . H20 H 0.2975 0.4071 0.7625 0.081 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 S1 0.0830(7) 0.0765(6) 0.1022(8) -0.0165(5) -0.0012(6) 0.0140(5) S2 0.0899(7) 0.0738(6) 0.0895(7) -0.0189(5) -0.0181(5) 0.0187(5) S3 0.1135(12) 0.1151(12) 0.0682(8) -0.0375(8) 0.0130(8) -0.0318(10) O3 0.1135(12) 0.1151(12) 0.0682(8) -0.0375(8) 0.0130(8) -0.0318(10) S4 0.1243(13) 0.1008(11) 0.0713(8) -0.0032(8) -0.0381(9) -0.0104(9) O4 0.1243(13) 0.1008(11) 0.0713(8) -0.0032(8) -0.0381(9) -0.0104(9) C5 0.160(5) 0.145(4) 0.060(2) -0.023(3) 0.006(3) -0.009(4) C6 0.181(6) 0.114(4) 0.094(3) -0.029(3) -0.063(4) 0.007(4) C7 0.074(2) 0.070(2) 0.087(2) -0.0169(18) 0.0074(18) -0.0185(17) C8 0.074(2) 0.0681(19) 0.082(2) -0.0119(17) -0.0060(18) -0.0156(16) C9 0.0654(18) 0.0563(16) 0.087(2) -0.0071(16) -0.0039(17) 0.0009(14) N10 0.076(2) 0.213(5) 0.079(2) -0.040(3) -0.0056(18) -0.053(3) N11 0.162(4) 0.124(3) 0.0489(16) -0.0128(19) -0.008(2) -0.041(3) C12 0.068(2) 0.137(3) 0.0465(16) -0.0258(19) 0.0004(15) -0.026(2) C13 0.0563(17) 0.100(2) 0.0425(14) -0.0196(15) -0.0013(12) -0.0153(16) C14 0.087(2) 0.114(3) 0.0392(15) -0.0192(18) -0.0053(15) -0.023(2) C15 0.0520(15) 0.0780(19) 0.0398(13) -0.0159(12) -0.0029(11) -0.0042(13) C16 0.0540(16) 0.096(2) 0.0467(14) -0.0183(15) -0.0005(12) -0.0184(15) C17 0.0557(16) 0.087(2) 0.0417(13) -0.0110(14) 0.0037(12) -0.0156(15) C18 0.0472(13) 0.0537(14) 0.0385(12) -0.0100(10) -0.0028(10) 0.0043(10) C19 0.0667(18) 0.0769(19) 0.0423(13) -0.0108(13) -0.0023(13) -0.0204(15) C20 0.0695(19) 0.094(2) 0.0410(14) -0.0089(14) 0.0023(13) -0.0244(17) _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 S1 C7 1.742(4) . ? S1 C9 1.762(4) . ? S2 C8 1.743(4) . ? S2 C9 1.757(3) . ? S3 C7 1.599(4) . ? S3 C5 1.682(6) . ? S4 C6 1.578(5) . ? S4 C8 1.584(4) . ? C5 C6 1.470(7) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C7 C8 1.329(5) . ? C9 C9 1.332(7) 2_556 ? N10 C12 1.129(4) . ? N11 C14 1.128(5) . ? C12 C13 1.473(4) . ? C13 C14 1.463(5) . ? C13 C15 1.535(4) . ? C13 H13 0.9600 . ? C15 C20 1.376(4) . ? C15 C16 1.376(4) . ? C16 C17 1.387(4) . ? C16 H16 0.9600 . ? C17 C18 1.391(4) . ? C17 H17 0.9600 . ? C18 C19 1.382(4) . ? C18 C18 1.497(5) 2_666 ? C19 C20 1.387(4) . ? C19 H19 0.9600 . ? C20 H20 0.9600 . ? 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 C7 S1 C9 93.89(17) . . ? C8 S2 C9 94.12(17) . . ? C7 S3 C5 98.7(2) . . ? C6 S4 C8 104.1(3) . . ? C6 C5 S3 116.4(4) . . ? C6 C5 H5A 108.2 . . ? S3 C5 H5A 108.2 . . ? C6 C5 H5B 108.2 . . ? S3 C5 H5B 108.2 . . ? H5A C5 H5B 107.3 . . ? C5 C6 S4 118.9(4) . . ? C5 C6 H6A 107.6 . . ? S4 C6 H6A 107.6 . . ? C5 C6 H6B 107.6 . . ? S4 C6 H6B 107.6 . . ? H6A C6 H6B 107.0 . . ? C8 C7 S3 129.4(3) . . ? C8 C7 S1 118.4(3) . . ? S3 C7 S1 112.2(2) . . ? C7 C8 S4 128.3(3) . . ? C7 C8 S2 118.1(3) . . ? S4 C8 S2 113.7(2) . . ? C9 C9 S2 122.0(4) 2_556 . ? C9 C9 S1 122.6(4) 2_556 . ? S2 C9 S1 115.5(2) . . ? N10 C12 C13 179.6(4) . . ? C14 C13 C12 109.6(3) . . ? C14 C13 C15 112.6(3) . . ? C12 C13 C15 113.4(3) . . ? C14 C13 H13 107.0 . . ? C12 C13 H13 107.0 . . ? C15 C13 H13 107.0 . . ? N11 C14 C13 178.9(5) . . ? C20 C15 C16 119.1(2) . . ? C20 C15 C13 119.0(3) . . ? C16 C15 C13 121.8(3) . . ? C15 C16 C17 120.0(3) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 121.8(3) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C19 C18 C17 117.0(2) . . ? C19 C18 C18 121.5(3) . 2_666 ? C17 C18 C18 121.5(3) . 2_666 ? C18 C19 C20 121.6(3) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C15 C20 C19 120.5(3) . . ? C15 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.290 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.044 #===END data_(DBTTF)(H2TCNDQ)2 _database_code_CSD 172688 _publ_section_exptl_refinement ? _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_structure_solution 'SIR92' _computing_structure_refinement 'Crystan 6.3' _computing_molecular_graphics 'ORTEP III' _computing_publication_material '' _chemical_formula_moiety 'C14 H8 S4, 0.5(C18 H10 N4)' _chemical_formula_sum 'C23 H13 N2 S4' _chemical_formula_weight 445.63 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z _symmetry_space_group_name_H-M 'P-1' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_Hall '-P 1' _cell_length_a 6.650(4) _cell_length_b 11.626(2) _cell_length_c 14.366(3) _cell_angle_alpha 108.72(1) _cell_angle_beta 91.70(3) _cell_angle_gamma 105.80(3) _cell_volume 1003.7(7) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.475 _diffrn_radiation_type 'Mo K-alpha' _diffrn_radiation_wavelength 0.71073 _cell_measurement_reflns_used 22 _cell_measurement_theta_min 0 _cell_measurement_theta_max 27.5 _diffrn_ambient_temperature 'Room Temperature' _exptl_crystal_F_000 458 _exptl_absorpt_coefficient_mu 0.493 _exptl_crystal_description 'Plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.2 _diffrn_measurement_device_type 'Mac Science MXCchi' _diffrn_measurement_method 'theta/2theta' _exptl_absorpt_correction_type 'none' _diffrn_radiation_monochromator 'Graphite' _diffrn_reflns_number 5171 _reflns_number_total 4270 _reflns_number_gt 4270 _reflns_observed_criterion 'refl_observed_if_I_>_2.00_sigma(I)' _refine_ls_extinction_method 'None' _diffrn_reflns_theta_max 27.50 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_ls_structure_factor_coef F _refine_ls_R_factor_obs 0.041 _refine_ls_wR_factor_obs 0.045 _refine_ls_goodness_of_fit_obs 0.746 _refine_ls_number_reflns 3631 _refine_ls_number_parameters 314 _refine_ls_weighting_scheme 'Unit' _refine_ls_hydrogen_treatment 'refall' _refine_ls_shift/esd_max 0.3130 _refine_ls_shift/esd_mean 0.0113 _refine_diff_density_min -0.31 _refine_diff_density_max 0.26 _atoms_sites_solution_primary 'direct method' _atoms_sites_solution_secondary 'Fourier difference' _atoms_sites_solution_hydrogens 'Fourier difference' _atom_type_scat_source 'International Tables (1974)' _diffrn_orient_matrix_type 'standard' _diffrn_orient_matrix_UB_11 0.00593 _diffrn_orient_matrix_UB_12 0.06177 _diffrn_orient_matrix_UB_13 -0.03559 _diffrn_orient_matrix_UB_21 -0.03391 _diffrn_orient_matrix_UB_22 -0.07153 _diffrn_orient_matrix_UB_23 -0.06493 _diffrn_orient_matrix_UB_31 -0.15379 _diffrn_orient_matrix_UB_32 -0.01087 _diffrn_orient_matrix_UB_33 0.00319 #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type S1 0.13910(12) 0.58020(8) 0.87300(6) 0.0477(4) 1.000 Uij S2 -0.27120(12) 0.58060(8) 0.94930(6) 0.0482(4) 1.000 Uij S3 0.38130(12) 0.78450(8) 1.08580(6) 0.0498(4) 1.000 Uij S4 -0.03390(12) 0.78050(8) 1.15830(6) 0.0480(4) 1.000 Uij N19 -0.0841(5) 0.7560(4) 0.5218(2) 0.077(2) 1.000 Uij N20 -0.6800(6) 0.6082(4) 0.6083(3) 0.098(3) 1.000 Uij C5 -0.0886(5) 0.4866(3) 0.7892(2) 0.042(1) 1.000 Uij C6 -0.0840(6) 0.4139(3) 0.6918(2) 0.051(2) 1.000 Uij C7 -0.2723(6) 0.3416(3) 0.6319(3) 0.057(2) 1.000 Uij C8 -0.4628(6) 0.3409(3) 0.6682(3) 0.057(2) 1.000 Uij C9 -0.4694(5) 0.4129(3) 0.7651(3) 0.051(2) 1.000 Uij C10 -0.2815(5) 0.4863(3) 0.8255(2) 0.042(1) 1.000 Uij C11 0.0051(4) 0.6392(3) 0.9727(2) 0.041(1) 1.000 Uij C12 0.3861(5) 0.8805(3) 1.2082(2) 0.045(1) 1.000 Uij C13 0.5703(6) 0.9559(3) 1.2702(3) 0.059(2) 1.000 Uij C14 0.5596(7) 1.0287(4) 1.3664(3) 0.069(2) 1.000 Uij C15 0.3668(7) 1.0256(4) 1.4003(3) 0.069(2) 1.000 Uij C16 0.1803(6) 0.9504(3) 1.3394(3) 0.060(2) 1.000 Uij C17 0.1907(5) 0.8780(3) 1.2428(2) 0.045(1) 1.000 Uij C18 0.1046(5) 0.7225(3) 1.0602(2) 0.042(1) 1.000 Uij C21 -0.1651(6) 0.7197(3) 0.5784(3) 0.057(2) 1.000 Uij C22 -0.2712(6) 0.6737(3) 0.6546(3) 0.059(2) 1.000 Uij C23 -0.5032(7) 0.6364(4) 0.6279(3) 0.068(2) 1.000 Uij C24 -0.1944(5) 0.7733(3) 0.7586(2) 0.049(2) 1.000 Uij C25 0.0167(6) 0.8139(4) 0.7930(3) 0.068(2) 1.000 Uij C26 0.0914(6) 0.9021(4) 0.8867(3) 0.067(2) 1.000 Uij C27 -0.0405(5) 0.9527(3) 0.9495(2) 0.045(1) 1.000 Uij C28 -0.2540(6) 0.9096(4) 0.9133(3) 0.065(2) 1.000 Uij C29 -0.3298(6) 0.8212(4) 0.8192(3) 0.067(2) 1.000 Uij H6 0.053(5) 0.419(3) 0.665(2) 0.051(9) 1.000 Uiso H9 -0.606(5) 0.407(3) 0.795(2) 0.06(1) 1.000 Uiso H8 -0.589(6) 0.296(4) 0.632(3) 0.08(1) 1.000 Uiso H16 0.035(6) 0.938(3) 1.363(3) 0.06(1) 1.000 Uiso H7 -0.259(6) 0.306(4) 0.563(3) 0.09(1) 1.000 Uiso H13 0.698(6) 0.958(4) 1.245(3) 0.07(1) 1.000 Uiso H15 0.353(6) 1.058(4) 1.471(3) 0.09(1) 1.000 Uiso H22 -0.234(6) 0.597(4) 0.657(3) 0.07(1) 1.000 Uiso H25 0.115(6) 0.779(4) 0.750(3) 0.09(1) 1.000 Uiso H14 0.698(7) 1.079(4) 1.408(3) 0.10(1) 1.000 Uiso H26 0.236(8) 0.923(5) 0.904(4) 0.12(2) 1.000 Uiso H28 -0.357(8) 0.946(5) 0.955(4) 0.13(2) 1.000 Uiso H29 -0.485(8) 0.802(5) 0.794(4) 0.14(2) 1.000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0379(4) 0.0519(5) 0.0383(4) 0.0117(3) 0.0080(3) 0.0039(3) S2 0.0384(4) 0.0540(5) 0.0380(4) 0.0133(3) 0.0079(3) 0.0057(3) S3 0.0400(4) 0.0493(5) 0.0435(4) 0.0074(3) 0.0079(3) 0.0044(3) S4 0.0428(4) 0.0458(4) 0.0403(4) 0.0103(3) 0.0096(3) 0.0032(3) N19 0.068(2) 0.092(3) 0.048(2) 0.023(2) 0.010(2) 0.011(2) N20 0.072(3) 0.101(3) 0.088(3) -0.016(2) -0.013(2) 0.035(2) C5 0.043(2) 0.037(1) 0.035(1) 0.012(1) 0.004(1) 0.009(1) C6 0.054(2) 0.048(2) 0.038(2) 0.018(2) 0.010(1) 0.009(1) C7 0.070(2) 0.050(2) 0.036(2) 0.019(2) 0.000(2) 0.004(1) C8 0.056(2) 0.049(2) 0.049(2) 0.010(2) -0.011(2) 0.006(2) C9 0.043(2) 0.048(2) 0.050(2) 0.011(1) 0.001(1) 0.013(1) C10 0.043(2) 0.036(1) 0.036(1) 0.013(1) 0.003(1) 0.010(1) C11 0.039(1) 0.038(1) 0.036(1) 0.012(1) 0.009(1) 0.009(1) C12 0.049(2) 0.035(1) 0.040(2) 0.010(1) 0.001(1) 0.007(1) C13 0.051(2) 0.049(2) 0.060(2) 0.010(2) -0.003(2) 0.007(2) C14 0.069(3) 0.055(2) 0.060(2) 0.012(2) -0.018(2) -0.002(2) C15 0.089(3) 0.058(2) 0.040(2) 0.025(2) -0.007(2) -0.005(2) C16 0.070(2) 0.053(2) 0.043(2) 0.023(2) 0.008(2) 0.007(2) C17 0.051(2) 0.035(1) 0.037(1) 0.012(1) 0.003(1) 0.008(1) C18 0.040(2) 0.037(1) 0.038(1) 0.011(1) 0.008(1) 0.009(1) C21 0.058(2) 0.054(2) 0.043(2) 0.021(2) -0.002(2) 0.002(2) C22 0.068(2) 0.042(2) 0.051(2) 0.014(2) -0.006(2) 0.011(2) C23 0.076(3) 0.054(2) 0.054(2) -0.004(2) -0.005(2) 0.018(2) C24 0.054(2) 0.040(2) 0.043(2) 0.010(1) 0.000(1) 0.017(1) C25 0.056(2) 0.080(3) 0.048(2) 0.028(2) 0.005(2) 0.004(2) C26 0.044(2) 0.085(3) 0.051(2) 0.022(2) 0.000(2) 0.006(2) C27 0.045(2) 0.042(2) 0.040(2) 0.011(1) 0.005(1) 0.021(1) C28 0.047(2) 0.073(2) 0.055(2) 0.015(2) 0.005(2) 0.007(2) C29 0.047(2) 0.072(3) 0.060(2) 0.010(2) -0.002(2) 0.007(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.755(3) . . yes S1 C11 1.759(4) . . yes S2 C10 1.752(3) . . yes S2 C11 1.757(3) . . yes S3 C12 1.748(4) . . yes S3 C18 1.763(3) . . yes S4 C17 1.754(3) . . yes S4 C18 1.759(4) . . yes N19 C21 1.119(6) . . yes N20 C23 1.131(6) . . yes C5 C6 1.390(5) . . yes C5 C10 1.399(5) . . yes C6 C7 1.383(5) . . yes C7 C8 1.383(6) . . yes C8 C9 1.384(5) . . yes C9 C10 1.386(5) . . yes C11 C18 1.333(4) . . yes C12 C13 1.383(5) . . yes C12 C17 1.401(5) . . yes C13 C14 1.385(6) . . yes C14 C15 1.380(7) . . yes C15 C16 1.386(6) . . yes C16 C17 1.388(5) . . yes C21 C22 1.483(6) . . yes C22 C23 1.486(6) . . yes C22 C24 1.535(5) . . yes C24 C25 1.373(5) . . yes C24 C29 1.374(6) . . yes C25 C26 1.381(6) . . yes C26 C27 1.384(6) . . yes C27 C27 1.487(4) . 2_577 yes C27 C28 1.392(5) . . yes C28 C29 1.387(6) . . yes C6 H6 1.00(4) . . yes C7 H7 0.96(5) . . yes C8 H8 0.90(4) . . yes C9 H9 1.01(4) . . yes C13 H13 0.94(5) . . yes C14 H14 1.00(5) . . yes C15 H15 0.98(5) . . yes C16 H16 1.03(4) . . yes C22 H22 1.00(4) . . yes C25 H25 0.99(5) . . yes C26 H26 0.93(6) . . yes C28 H28 1.01(6) . . yes C29 H29 1.02(6) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C11 95.7(2) . . . yes C10 S2 C11 95.7(2) . . . yes C12 S3 C18 95.8(2) . . . yes C17 S4 C18 95.7(2) . . . yes S1 C5 C6 123.4(3) . . . yes S1 C5 C10 116.5(3) . . . yes C6 C5 C10 120.1(3) . . . yes C5 C6 C7 119.0(4) . . . yes C6 C7 C8 120.7(4) . . . yes C7 C8 C9 120.8(4) . . . yes C8 C9 C10 118.9(4) . . . yes S2 C10 C5 116.8(3) . . . yes S2 C10 C9 122.8(3) . . . yes C5 C10 C9 120.4(3) . . . yes S1 C11 S2 115.3(2) . . . yes S1 C11 C18 122.8(3) . . . yes S2 C11 C18 121.9(3) . . . yes S3 C12 C13 123.3(3) . . . yes S3 C12 C17 116.7(3) . . . yes C13 C12 C17 120.0(3) . . . yes C12 C13 C14 119.4(4) . . . yes C13 C14 C15 120.3(4) . . . yes C14 C15 C16 121.1(4) . . . yes C15 C16 C17 118.6(4) . . . yes S4 C17 C12 116.6(3) . . . yes S4 C17 C16 122.9(3) . . . yes C12 C17 C16 120.5(3) . . . yes S3 C18 S4 115.2(2) . . . yes S3 C18 C11 123.1(3) . . . yes S4 C18 C11 121.7(3) . . . yes N19 C21 C22 179.1(4) . . . yes C21 C22 C23 109.1(4) . . . yes C21 C22 C24 111.0(3) . . . yes C23 C22 C24 113.0(4) . . . yes N20 C23 C22 179.5(5) . . . yes C22 C24 C25 118.7(4) . . . yes C22 C24 C29 122.4(4) . . . yes C25 C24 C29 118.9(4) . . . yes C24 C25 C26 120.4(4) . . . yes C25 C26 C27 122.2(4) . . . yes C26 C27 C27 122.0(3) . . 2_577 yes C26 C27 C28 116.4(4) . . . yes C27 C27 C28 121.6(3) 2_577 . . yes C27 C28 C29 121.7(4) . . . yes C24 C29 C28 120.4(4) . . . yes C5 C6 H6 119.8(19) . . . yes C7 C6 H6 121.1(19) . . . yes C6 C7 H7 114.6(25) . . . yes C8 C7 H7 123.8(25) . . . yes C7 C8 H8 124.0(27) . . . yes C9 C8 H8 115.2(27) . . . yes C8 C9 H9 121.9(20) . . . yes C10 C9 H9 119.0(20) . . . yes C12 C13 H13 118.3(24) . . . yes C14 C13 H13 122.2(24) . . . yes C13 C14 H14 115.3(27) . . . yes C15 C14 H14 124.3(26) . . . yes C14 C15 H15 122.4(25) . . . yes C16 C15 H15 114.8(25) . . . yes C15 C16 H16 123.8(20) . . . yes C17 C16 H16 117.4(20) . . . yes C21 C22 H22 110.6(22) . . . yes C23 C22 H22 107.8(22) . . . yes C24 C22 H22 105.1(22) . . . yes C24 C25 H25 119.2(25) . . . yes C26 C25 H25 120.4(25) . . . yes C25 C26 H26 114.5(32) . . . yes C27 C26 H26 123.3(32) . . . yes C27 C28 H28 120.0(31) . . . yes C29 C28 H28 118.2(31) . . . yes C24 C29 H29 121.4(31) . . . yes C28 C29 H29 117.7(31) . . . yes #===END data_(H-DAD+)2(TCNDQ2-) _database_code_CSD 172689 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(H-DAD+)2(TCNDQ2-)' _chemical_melting_point ? _chemical_formula_moiety '2(C10 H17 N2), C18 H8 N4' _chemical_formula_sum 'C38 H42 N8' _chemical_formula_weight 610.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'N' 'N' 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0000 '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' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P21221' _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' '-x+1/2, -y, z+1/2' 'x+1/2, -y, -z+1/2' _cell_length_a 14.2080(17) _cell_length_b 16.706(2) _cell_length_c 21.0540(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4997.4(9) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 0 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'block' _exptl_crystal_colour 'dark-yellow' _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1956 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Mac Science DIP-2020K' _diffrn_measurement_method 'theta/2theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18628 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.25 _reflns_number_total 5157 _reflns_number_gt 4069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1675P)^2^+1.5418P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 5157 _refine_ls_number_parameters 625 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0880 _refine_ls_wR_factor_ref 0.2746 _refine_ls_wR_factor_gt 0.2483 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 N1 N 0.6904(4) 0.2657(3) 0.4125(2) 0.0709(13) Uani 1 1 d . . . H1A H 0.6715 0.3204 0.4184 0.085 Uiso 0.83 1 calc PR . . H1B H 0.7393 0.2527 0.4421 0.085 Uiso 0.83 1 calc PR . . H1C H 0.6374 0.2311 0.4194 0.085 Uiso 0.83 1 calc PR . . N2 N 0.8454(3) 0.2236(2) 0.16885(17) 0.0474(9) Uani 1 1 d . . . H2A H 0.8774 0.1730 0.1676 0.057 Uiso 0.83 1 calc PR . . H2B H 0.8894 0.2657 0.1602 0.057 Uiso 0.83 1 calc PR . . H2C H 0.7965 0.2242 0.1374 0.057 Uiso 0.83 1 calc PR . . C3 C 0.7244(3) 0.2553(3) 0.3494(2) 0.0472(11) Uani 1 1 d . . . C4 C 0.7337(3) 0.1778(3) 0.3247(2) 0.0461(10) Uani 1 1 d . . . C5 C 0.7747(3) 0.1685(2) 0.26476(19) 0.0413(9) Uani 1 1 d . . . C6 C 0.8041(3) 0.2354(2) 0.23194(19) 0.0383(9) Uani 1 1 d . . . C7 C 0.7922(3) 0.3130(2) 0.2546(2) 0.0435(9) Uani 1 1 d . . . C8 C 0.7514(3) 0.3229(3) 0.3150(2) 0.0453(10) Uani 1 1 d . . . C9 C 0.7042(5) 0.1067(4) 0.3642(3) 0.0811(18) Uani 1 1 d . . . H9A H 0.7542 0.0680 0.3650 0.097 Uiso 1 1 calc R . . H9B H 0.6490 0.0828 0.3460 0.097 Uiso 1 1 calc R . . H9C H 0.6907 0.1239 0.4067 0.097 Uiso 1 1 calc R . . C10 C 0.7815(4) 0.0864(3) 0.2361(2) 0.0595(13) Uani 1 1 d . . . H10A H 0.7437 0.0498 0.2603 0.071 Uiso 1 1 calc R . . H10B H 0.8459 0.0690 0.2367 0.071 Uiso 1 1 calc R . . H10C H 0.7592 0.0880 0.1931 0.071 Uiso 1 1 calc R . . C11 C 0.8204(4) 0.3846(3) 0.2159(3) 0.0630(14) Uani 1 1 d . . . H11A H 0.8649 0.4161 0.2393 0.076 Uiso 1 1 calc R . . H11B H 0.7658 0.4163 0.2066 0.076 Uiso 1 1 calc R . . H11C H 0.8487 0.3670 0.1769 0.076 Uiso 1 1 calc R . . C12 C 0.7369(4) 0.4047(3) 0.3434(3) 0.0657(14) Uani 1 1 d . . . H12A H 0.7747 0.4430 0.3210 0.079 Uiso 1 1 calc R . . H12B H 0.7549 0.4040 0.3873 0.079 Uiso 1 1 calc R . . H12C H 0.6717 0.4193 0.3400 0.079 Uiso 1 1 calc R . . N13 N 0.1573(3) 0.2689(3) 0.16612(18) 0.0614(11) Uani 1 1 d . . . H13A H 0.1130 0.2268 0.1745 0.074 Uiso 0.83 1 calc PR . . H13B H 0.1255 0.3196 0.1675 0.074 Uiso 0.83 1 calc PR . . H13C H 0.2060 0.2679 0.1977 0.074 Uiso 0.83 1 calc PR . . N14 N 0.3101(3) 0.2281(3) -0.07910(19) 0.0622(11) Uani 1 1 d . . . H14A H 0.3356 0.2777 -0.0944 0.075 Uiso 0.83 1 calc PR . . H14B H 0.2592 0.2117 -0.1061 0.075 Uiso 0.83 1 calc PR . . H14C H 0.3582 0.1878 -0.0794 0.075 Uiso 0.83 1 calc PR . . C15 C 0.1995(3) 0.2572(3) 0.1020(2) 0.0444(10) Uani 1 1 d . . . C16 C 0.2171(4) 0.1797(3) 0.0798(2) 0.0513(11) Uani 1 1 d . . . C17 C 0.2567(3) 0.1702(3) 0.0201(2) 0.0515(11) Uani 1 1 d . . . C18 C 0.2764(3) 0.2386(3) -0.0164(2) 0.0457(10) Uani 1 1 d . . . C19 C 0.2605(3) 0.3147(3) 0.0068(2) 0.0492(10) Uani 1 1 d . . . C20 C 0.2229(3) 0.3258(3) 0.0678(2) 0.0451(10) Uani 1 1 d . . . C21 C 0.1970(5) 0.1081(3) 0.1218(3) 0.084(2) Uani 1 1 d . . . H21A H 0.1441 0.1197 0.1486 0.101 Uiso 1 1 calc R . . H21B H 0.2511 0.0969 0.1476 0.101 Uiso 1 1 calc R . . H21C H 0.1830 0.0625 0.0958 0.101 Uiso 1 1 calc R . . C22 C 0.2762(5) 0.0886(3) -0.0050(3) 0.0812(18) Uani 1 1 d . . . H22A H 0.3354 0.0886 -0.0270 0.097 Uiso 1 1 calc R . . H22B H 0.2270 0.0733 -0.0339 0.097 Uiso 1 1 calc R . . H22C H 0.2787 0.0512 0.0296 0.097 Uiso 1 1 calc R . . C23 C 0.2828(5) 0.3868(3) -0.0330(3) 0.0766(17) Uani 1 1 d . . . H23A H 0.2918 0.4324 -0.0059 0.092 Uiso 1 1 calc R . . H23B H 0.2317 0.3970 -0.0617 0.092 Uiso 1 1 calc R . . H23C H 0.3393 0.3772 -0.0568 0.092 Uiso 1 1 calc R . . C24 C 0.2106(4) 0.4087(3) 0.0958(3) 0.0655(14) Uani 1 1 d . . . H24A H 0.1888 0.4447 0.0634 0.079 Uiso 1 1 calc R . . H24B H 0.2698 0.4273 0.1120 0.079 Uiso 1 1 calc R . . H24C H 0.1654 0.4067 0.1296 0.079 Uiso 1 1 calc R . . N25 N 0.1525(3) 0.2659(3) 0.4978(2) 0.0672(12) Uani 1 1 d . . . H25A H 0.1222 0.2161 0.5077 0.081 Uiso 0.83 1 calc PR . . H25B H 0.1065 0.3080 0.4970 0.081 Uiso 0.83 1 calc PR . . H25C H 0.1991 0.2776 0.5295 0.081 Uiso 0.83 1 calc PR . . N26 N 0.3144(4) 0.2537(3) 0.2542(2) 0.0771(15) Uani 1 1 d . . . H26A H 0.3428 0.3046 0.2451 0.092 Uiso 0.83 1 calc PR . . H26B H 0.2641 0.2440 0.2247 0.092 Uiso 0.83 1 calc PR . . H26C H 0.3608 0.2122 0.2502 0.092 Uiso 0.83 1 calc PR . . C27 C 0.1978(3) 0.2600(3) 0.4356(2) 0.0466(10) Uani 1 1 d . . . C28 C 0.2116(3) 0.1847(3) 0.4073(2) 0.0482(11) Uani 1 1 d . . . C29 C 0.2525(3) 0.1826(3) 0.3468(2) 0.0487(11) Uani 1 1 d . . . C30 C 0.2781(3) 0.2541(3) 0.3173(2) 0.0493(11) Uani 1 1 d . . . C31 C 0.2675(3) 0.3275(3) 0.3482(2) 0.0514(11) Uani 1 1 d . . . C32 C 0.2265(3) 0.3306(3) 0.4083(2) 0.0483(11) Uani 1 1 d . . . C33 C 0.1890(5) 0.1092(3) 0.4427(3) 0.086(2) Uani 1 1 d . . . H33A H 0.1908 0.0646 0.4140 0.103 Uiso 1 1 calc R . . H33B H 0.1273 0.1134 0.4609 0.103 Uiso 1 1 calc R . . H33C H 0.2344 0.1013 0.4759 0.103 Uiso 1 1 calc R . . C34 C 0.2669(5) 0.1034(3) 0.3130(3) 0.085(2) Uani 1 1 d . . . H34A H 0.2863 0.0636 0.3432 0.102 Uiso 1 1 calc R . . H34B H 0.3145 0.1094 0.2810 0.102 Uiso 1 1 calc R . . H34C H 0.2089 0.0870 0.2935 0.102 Uiso 1 1 calc R . . C35 C 0.3002(5) 0.4038(4) 0.3155(3) 0.085(2) Uani 1 1 d . . . H35A H 0.3657 0.3991 0.3048 0.101 Uiso 1 1 calc R . . H35B H 0.2914 0.4485 0.3435 0.101 Uiso 1 1 calc R . . H35C H 0.2642 0.4118 0.2774 0.101 Uiso 1 1 calc R . . C36 C 0.2165(4) 0.4112(3) 0.4406(3) 0.0736(17) Uani 1 1 d . . . H36A H 0.1951 0.4501 0.4103 0.088 Uiso 1 1 calc R . . H36B H 0.2763 0.4275 0.4574 0.088 Uiso 1 1 calc R . . H36C H 0.1717 0.4071 0.4746 0.088 Uiso 1 1 calc R . . N37 N 0.5304(4) -0.1636(4) 0.2708(2) 0.0866(17) Uani 1 1 d . . . N38 N 0.4526(6) -0.1600(6) 0.0700(3) 0.177(5) Uani 1 1 d . . . N39 N 0.5813(5) 0.5960(5) 0.2591(3) 0.115(2) Uani 1 1 d . . . N40 N 0.4522(5) 0.6087(6) 0.0708(3) 0.145(3) Uani 1 1 d . . . C41 C 0.5141(4) -0.1307(4) 0.2255(3) 0.0772(17) Uani 1 1 d . . . C42 C 0.4950(4) -0.0855(4) 0.1698(3) 0.0749(17) Uani 1 1 d . . . C43 C 0.4717(6) -0.1266(6) 0.1158(3) 0.115(3) Uani 1 1 d . . . C44 C 0.4949(3) -0.0005(5) 0.1688(2) 0.0761(19) Uani 1 1 d . . . C45 C 0.4789(5) 0.0461(5) 0.1132(3) 0.091(2) Uani 1 1 d . . . H45 H 0.4688 0.0188 0.0736 0.110 Uiso 1 1 calc R . . C46 C 0.4775(5) 0.1279(5) 0.1138(3) 0.096(2) Uani 1 1 d . . . H46 H 0.4606 0.1556 0.0755 0.116 Uiso 1 1 calc R . . C47 C 0.4994(4) 0.1724(4) 0.1674(3) 0.0754(17) Uani 1 1 d . . . C48 C 0.5174(4) 0.1246(5) 0.2219(3) 0.0802(19) Uani 1 1 d . . . H48 H 0.5333 0.1520 0.2605 0.096 Uiso 1 1 calc R . . C49 C 0.5142(4) 0.0455(4) 0.2237(3) 0.0783(17) Uani 1 1 d . . . H49 H 0.5252 0.0187 0.2633 0.094 Uiso 1 1 calc R . . C50 C 0.5008(4) 0.2592(5) 0.1667(3) 0.084(2) Uani 1 1 d . . . C51 C 0.4626(5) 0.3065(5) 0.1170(3) 0.091(2) Uani 1 1 d . . . H51 H 0.4326 0.2795 0.0822 0.109 Uiso 1 1 calc R . . C52 C 0.4661(5) 0.3881(6) 0.1160(3) 0.099(3) Uani 1 1 d . . . H52 H 0.4384 0.4156 0.0806 0.119 Uiso 1 1 calc R . . C53 C 0.5084(4) 0.4341(4) 0.1644(3) 0.0736(17) Uani 1 1 d . . . C54 C 0.5479(4) 0.3864(5) 0.2134(3) 0.088(2) Uani 1 1 d . . . H54 H 0.5778 0.4136 0.2482 0.106 Uiso 1 1 calc R . . C55 C 0.5465(4) 0.3046(5) 0.2148(3) 0.085(2) Uani 1 1 d . . . H55 H 0.5772 0.2770 0.2490 0.102 Uiso 1 1 calc R . . C56 C 0.5492(4) 0.5623(4) 0.2160(3) 0.0807(17) Uani 1 1 d . . . C57 C 0.5111(4) 0.5202(5) 0.1645(3) 0.087(2) Uani 1 1 d . . . C58 C 0.4787(5) 0.5680(5) 0.1139(3) 0.100(3) Uani 1 1 d . . . N59 N -0.0264(3) 0.3250(2) 0.1013(2) 0.0612(11) Uani 1 1 d . . . N60 N -0.0715(4) 1.0856(3) 0.0946(2) 0.0766(14) Uani 1 1 d . . . C61 C -0.0162(3) 0.3608(2) 0.0547(2) 0.0484(10) Uani 1 1 d . . . C62 C 0.0000 0.4049(3) 0.0000 0.0451(14) Uani 1 2 d S . . C63 C 0.0000 0.4924(3) 0.0000 0.0463(14) Uani 1 2 d S . . C64 C -0.0119(3) 0.5365(2) 0.0555(2) 0.0483(10) Uani 1 1 d . . . H64 H -0.0208 0.5084 0.0948 0.058 Uiso 1 1 calc R . . C65 C -0.0115(4) 0.6200(2) 0.0562(2) 0.0500(11) Uani 1 1 d . . . H65 H -0.0191 0.6481 0.0957 0.060 Uiso 1 1 calc R . . C66 C 0.0000 0.6629(3) 0.0000 0.0418(13) Uani 1 2 d S . . C67 C 0.0000 0.7527(3) 0.0000 0.0460(15) Uani 1 2 d S . . C68 C -0.0456(3) 0.7974(2) 0.0470(2) 0.0476(10) Uani 1 1 d . . . H68 H -0.0785 0.7697 0.0802 0.057 Uiso 1 1 calc R . . C69 C -0.0448(4) 0.8802(3) 0.0474(2) 0.0537(11) Uani 1 1 d . . . H69 H -0.0760 0.9081 0.0812 0.064 Uiso 1 1 calc R . . C70 C 0.0000 1.0107(4) 0.0000 0.0614(19) Uani 1 2 d S . . C71 C 0.0000 0.9241(4) 0.0000 0.0503(15) Uani 1 2 d S . . C72 C -0.0398(4) 1.0537(3) 0.0513(3) 0.0643(14) 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 N1 0.066(3) 0.101(4) 0.046(3) 0.000(2) 0.005(2) 0.012(3) N2 0.059(2) 0.0394(17) 0.044(2) -0.0017(14) 0.0086(16) -0.0002(17) C3 0.045(2) 0.061(3) 0.036(2) 0.0011(17) 0.0007(18) 0.009(2) C4 0.053(2) 0.049(2) 0.036(2) 0.0108(18) 0.0040(19) 0.002(2) C5 0.045(2) 0.0359(19) 0.043(2) 0.0032(16) 0.0023(18) -0.0007(17) C6 0.043(2) 0.0374(19) 0.034(2) 0.0008(15) 0.0013(17) -0.0015(17) C7 0.050(2) 0.040(2) 0.040(2) -0.0040(17) 0.0016(18) -0.0016(18) C8 0.053(2) 0.045(2) 0.038(2) -0.0081(17) 0.0022(19) 0.0049(19) C9 0.099(4) 0.070(4) 0.074(4) 0.020(3) 0.028(3) 0.003(3) C10 0.070(3) 0.039(2) 0.069(3) 0.000(2) 0.012(3) 0.000(2) C11 0.092(4) 0.037(2) 0.060(3) -0.003(2) 0.012(3) -0.002(2) C12 0.085(4) 0.054(3) 0.058(3) -0.021(2) 0.004(3) 0.009(3) N13 0.066(3) 0.076(3) 0.043(2) -0.0004(19) 0.0081(18) 0.007(2) N14 0.065(3) 0.084(3) 0.038(2) -0.0036(19) 0.0106(18) 0.011(2) C15 0.046(2) 0.052(2) 0.034(2) -0.0027(17) 0.0021(19) 0.0037(18) C16 0.063(3) 0.041(2) 0.050(3) 0.0062(18) -0.006(2) -0.006(2) C17 0.064(3) 0.047(2) 0.044(3) -0.0041(17) -0.008(2) 0.001(2) C18 0.041(2) 0.057(2) 0.038(3) -0.0024(17) 0.0012(17) 0.0032(19) C19 0.047(2) 0.052(2) 0.049(3) 0.003(2) -0.004(2) 0.001(2) C20 0.046(2) 0.043(2) 0.046(3) -0.0004(18) -0.0031(18) 0.0051(18) C21 0.127(6) 0.050(3) 0.074(4) 0.016(3) 0.016(4) -0.017(3) C22 0.117(5) 0.055(3) 0.072(4) -0.012(3) -0.001(3) 0.004(3) C23 0.102(4) 0.063(3) 0.065(4) 0.022(3) 0.009(3) -0.011(3) C24 0.073(3) 0.048(3) 0.075(4) -0.012(2) -0.004(3) 0.005(2) N25 0.064(3) 0.101(3) 0.037(2) -0.001(2) 0.0101(18) -0.021(2) N26 0.060(3) 0.129(5) 0.042(3) -0.004(2) 0.005(2) 0.001(3) C27 0.047(2) 0.058(3) 0.036(2) -0.0064(18) 0.0016(18) -0.0037(19) C28 0.060(3) 0.040(2) 0.045(3) 0.0053(17) -0.011(2) -0.006(2) C29 0.055(3) 0.045(2) 0.047(3) -0.0107(18) -0.014(2) 0.007(2) C30 0.044(2) 0.069(3) 0.035(2) -0.0007(18) 0.0005(18) 0.007(2) C31 0.050(2) 0.047(2) 0.058(3) 0.009(2) -0.002(2) -0.006(2) C32 0.048(2) 0.047(2) 0.050(3) -0.0079(19) -0.0054(19) 0.005(2) C33 0.103(5) 0.060(3) 0.096(5) 0.036(3) -0.033(4) -0.029(3) C34 0.097(4) 0.063(3) 0.096(5) -0.032(3) -0.030(4) 0.021(3) C35 0.100(5) 0.071(4) 0.082(4) 0.040(3) -0.018(4) -0.030(3) C36 0.078(4) 0.056(3) 0.087(4) -0.027(3) -0.014(3) 0.012(3) N37 0.089(4) 0.124(5) 0.047(3) 0.009(3) -0.011(2) 0.014(3) N38 0.238(9) 0.232(9) 0.062(4) 0.031(5) -0.059(5) -0.166(8) N39 0.115(5) 0.154(6) 0.077(4) -0.026(4) -0.010(3) -0.033(5) N40 0.139(6) 0.218(9) 0.078(5) -0.027(5) -0.027(4) 0.088(7) C41 0.051(3) 0.125(5) 0.055(4) 0.003(3) 0.001(2) 0.001(3) C42 0.065(4) 0.105(5) 0.056(4) 0.014(3) -0.011(3) -0.019(3) C43 0.109(6) 0.170(8) 0.066(5) 0.033(4) -0.027(4) -0.091(6) C44 0.034(3) 0.152(6) 0.042(3) 0.014(3) -0.005(2) -0.011(3) C45 0.092(5) 0.122(6) 0.060(4) 0.015(4) -0.015(3) -0.040(4) C46 0.098(5) 0.142(7) 0.049(4) 0.012(4) -0.022(3) -0.026(5) C47 0.063(4) 0.101(5) 0.062(4) -0.001(3) -0.005(3) -0.011(3) C48 0.059(3) 0.142(6) 0.040(3) 0.001(3) -0.010(2) 0.006(4) C49 0.069(4) 0.110(5) 0.056(4) -0.003(3) -0.009(3) 0.017(4) C50 0.031(2) 0.178(7) 0.043(3) -0.009(3) -0.0021(19) 0.009(3) C51 0.075(4) 0.136(6) 0.061(4) -0.028(4) -0.016(3) 0.038(4) C52 0.069(4) 0.180(8) 0.049(4) -0.024(4) -0.023(3) 0.028(5) C53 0.049(3) 0.113(5) 0.059(4) -0.010(3) -0.005(3) 0.008(3) C54 0.071(4) 0.149(7) 0.045(4) -0.006(4) -0.016(3) -0.008(4) C55 0.069(4) 0.124(6) 0.061(4) 0.009(4) -0.016(3) -0.029(4) C56 0.068(4) 0.108(5) 0.066(4) -0.014(3) 0.004(3) -0.001(3) C57 0.059(3) 0.163(7) 0.040(4) -0.011(3) 0.000(3) 0.022(4) C58 0.073(4) 0.166(8) 0.062(5) -0.019(4) -0.014(3) 0.042(5) N59 0.070(3) 0.054(2) 0.060(3) 0.0083(19) 0.011(2) -0.001(2) N60 0.103(4) 0.056(2) 0.071(3) -0.015(2) 0.011(3) -0.002(3) C61 0.051(3) 0.045(2) 0.050(3) -0.0026(19) 0.008(2) 0.0041(19) C62 0.050(4) 0.042(3) 0.043(3) 0.000 0.006(3) 0.000 C63 0.048(3) 0.042(3) 0.049(4) 0.000 0.002(3) 0.000 C64 0.057(3) 0.045(2) 0.042(2) 0.0034(17) 0.007(2) 0.000(2) C65 0.056(3) 0.045(2) 0.049(3) -0.0036(19) 0.004(2) 0.000(2) C66 0.036(3) 0.046(3) 0.044(3) 0.000 0.001(3) 0.000 C67 0.048(4) 0.043(3) 0.046(4) 0.000 0.003(3) 0.000 C68 0.050(2) 0.044(2) 0.048(3) -0.0016(18) 0.010(2) -0.0043(19) C69 0.065(3) 0.044(2) 0.053(3) -0.002(2) 0.012(2) 0.002(2) C70 0.078(5) 0.039(3) 0.067(5) 0.000 0.013(4) 0.000 C71 0.064(4) 0.043(3) 0.044(4) 0.000 -0.001(3) 0.000 C72 0.087(4) 0.046(2) 0.060(3) -0.001(2) 0.002(3) 0.006(2) _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 N1 C3 1.423(6) . ? N1 H1A 0.9599 . ? N1 H1B 0.9599 . ? N1 H1C 0.9599 . ? N2 C6 1.465(5) . ? N2 H2A 0.9599 . ? N2 H2B 0.9599 . ? N2 H2C 0.9599 . ? C3 C8 1.395(6) . ? C3 C4 1.401(6) . ? C4 C5 1.399(6) . ? C4 C9 1.510(6) . ? C5 C6 1.380(5) . ? C5 C10 1.501(6) . ? C6 C7 1.391(5) . ? C7 C8 1.407(6) . ? C7 C11 1.502(6) . ? C8 C12 1.506(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N13 C15 1.490(5) . ? N13 H13A 0.9599 . ? N13 H13B 0.9599 . ? N13 H13C 0.9599 . ? N14 C18 1.416(5) . ? N14 H14A 0.9599 . ? N14 H14B 0.9599 . ? N14 H14C 0.9599 . ? C15 C20 1.395(6) . ? C15 C16 1.399(6) . ? C16 C17 1.387(7) . ? C16 C21 1.513(6) . ? C17 C18 1.405(6) . ? C17 C22 1.489(6) . ? C18 C19 1.380(6) . ? C19 C20 1.403(7) . ? C19 C23 1.500(6) . ? C20 C24 1.515(6) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? N25 C27 1.462(6) . ? N25 H25A 0.9599 . ? N25 H25B 0.9599 . ? N25 H25C 0.9599 . ? N26 C30 1.426(6) . ? N26 H26A 0.9599 . ? N26 H26B 0.9599 . ? N26 H26C 0.9599 . ? C27 C32 1.374(6) . ? C27 C28 1.407(6) . ? C28 C29 1.400(7) . ? C28 C33 1.500(6) . ? C29 C30 1.395(7) . ? C29 C34 1.516(6) . ? C30 C31 1.395(6) . ? C31 C32 1.392(7) . ? C31 C35 1.522(6) . ? C32 C36 1.516(6) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? N37 C41 1.124(7) . ? N38 C43 1.146(10) . ? N39 C56 1.161(8) . ? N40 C58 1.194(10) . ? C41 C42 1.421(8) . ? C42 C43 1.370(9) . ? C42 C44 1.421(9) . ? C44 C49 1.416(8) . ? C44 C45 1.424(8) . ? C45 C46 1.367(10) . ? C45 H45 0.9600 . ? C46 C47 1.387(9) . ? C46 H46 0.9600 . ? C47 C48 1.421(8) . ? C47 C50 1.451(10) . ? C48 C49 1.323(9) . ? C48 H48 0.9600 . ? C49 H49 0.9600 . ? C50 C51 1.418(9) . ? C50 C55 1.421(9) . ? C51 C52 1.365(11) . ? C51 H51 0.9600 . ? C52 C53 1.410(9) . ? C52 H52 0.9600 . ? C53 C54 1.419(9) . ? C53 C57 1.440(10) . ? C54 C55 1.368(10) . ? C54 H54 0.9600 . ? C55 H55 0.9600 . ? C56 C57 1.401(9) . ? C57 C58 1.409(9) . ? N59 C61 1.158(6) . ? N60 C72 1.147(6) . ? C61 C62 1.386(5) . ? C62 C61 1.386(5) 2 ? C62 C63 1.462(8) . ? C63 C64 1.392(5) 2 ? C63 C64 1.392(5) . ? C64 C65 1.395(6) . ? C64 H64 0.9600 . ? C65 C66 1.393(5) . ? C65 H65 0.9600 . ? C66 C65 1.393(5) 2 ? C66 C67 1.501(8) . ? C67 C68 1.399(5) 2 ? C67 C68 1.399(5) . ? C68 C69 1.383(6) . ? C68 H68 0.9600 . ? C69 C71 1.393(5) . ? C69 H69 0.9600 . ? C70 C72 1.416(6) 2 ? C70 C72 1.416(6) . ? C70 C71 1.446(8) . ? C71 C69 1.393(6) 2 ? 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 C3 N1 H1A 109.5 . . ? C3 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C3 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C6 N2 H2A 109.5 . . ? C6 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C6 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C8 C3 C4 121.9(4) . . ? C8 C3 N1 118.6(4) . . ? C4 C3 N1 119.4(4) . . ? C5 C4 C3 118.5(4) . . ? C5 C4 C9 121.6(4) . . ? C3 C4 C9 119.8(4) . . ? C6 C5 C4 119.2(4) . . ? C6 C5 C10 121.3(4) . . ? C4 C5 C10 119.4(4) . . ? C5 C6 C7 123.1(4) . . ? C5 C6 N2 117.7(4) . . ? C7 C6 N2 119.1(4) . . ? C6 C7 C8 118.0(4) . . ? C6 C7 C11 121.5(4) . . ? C8 C7 C11 120.5(4) . . ? C3 C8 C7 119.2(4) . . ? C3 C8 C12 119.4(4) . . ? C7 C8 C12 121.4(4) . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 N13 H13A 109.5 . . ? C15 N13 H13B 109.5 . . ? H13A N13 H13B 109.5 . . ? C15 N13 H13C 109.5 . . ? H13A N13 H13C 109.5 . . ? H13B N13 H13C 109.5 . . ? C18 N14 H14A 109.5 . . ? C18 N14 H14B 109.5 . . ? H14A N14 H14B 109.5 . . ? C18 N14 H14C 109.5 . . ? H14A N14 H14C 109.5 . . ? H14B N14 H14C 109.5 . . ? C20 C15 C16 123.1(4) . . ? C20 C15 N13 117.1(4) . . ? C16 C15 N13 119.7(4) . . ? C17 C16 C15 118.7(4) . . ? C17 C16 C21 121.1(4) . . ? C15 C16 C21 120.1(5) . . ? C16 C17 C18 118.9(4) . . ? C16 C17 C22 120.1(5) . . ? C18 C17 C22 121.0(4) . . ? C19 C18 C17 121.6(4) . . ? C19 C18 N14 119.9(4) . . ? C17 C18 N14 118.4(4) . . ? C18 C19 C20 120.5(4) . . ? C18 C19 C23 120.5(5) . . ? C20 C19 C23 119.0(4) . . ? C15 C20 C19 117.1(4) . . ? C15 C20 C24 121.5(4) . . ? C19 C20 C24 121.4(4) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C27 N25 H25A 109.5 . . ? C27 N25 H25B 109.5 . . ? H25A N25 H25B 109.5 . . ? C27 N25 H25C 109.5 . . ? H25A N25 H25C 109.5 . . ? H25B N25 H25C 109.5 . . ? C30 N26 H26A 109.5 . . ? C30 N26 H26B 109.5 . . ? H26A N26 H26B 109.5 . . ? C30 N26 H26C 109.5 . . ? H26A N26 H26C 109.5 . . ? H26B N26 H26C 109.5 . . ? C32 C27 C28 123.2(4) . . ? C32 C27 N25 116.6(4) . . ? C28 C27 N25 120.2(4) . . ? C29 C28 C27 117.9(4) . . ? C29 C28 C33 121.3(5) . . ? C27 C28 C33 120.7(5) . . ? C28 C29 C30 119.4(4) . . ? C28 C29 C34 120.3(5) . . ? C30 C29 C34 120.3(5) . . ? C29 C30 C31 121.2(4) . . ? C29 C30 N26 120.3(5) . . ? C31 C30 N26 118.5(5) . . ? C32 C31 C30 120.0(4) . . ? C32 C31 C35 120.5(5) . . ? C30 C31 C35 119.4(5) . . ? C27 C32 C31 118.2(4) . . ? C27 C32 C36 123.1(5) . . ? C31 C32 C36 118.7(4) . . ? C28 C33 H33A 109.5 . . ? C28 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C28 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C29 C34 H34A 109.5 . . ? C29 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C29 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C31 C35 H35A 109.5 . . ? C31 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C31 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C32 C36 H36A 109.5 . . ? C32 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C32 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N37 C41 C42 177.2(8) . . ? C43 C42 C41 117.8(7) . . ? C43 C42 C44 119.2(6) . . ? C41 C42 C44 122.9(5) . . ? N38 C43 C42 178.9(8) . . ? C49 C44 C45 114.0(7) . . ? C49 C44 C42 122.0(5) . . ? C45 C44 C42 124.0(6) . . ? C46 C45 C44 122.7(7) . . ? C46 C45 H45 118.6 . . ? C44 C45 H45 118.6 . . ? C45 C46 C47 122.7(7) . . ? C45 C46 H46 118.7 . . ? C47 C46 H46 118.7 . . ? C46 C47 C48 113.4(7) . . ? C46 C47 C50 122.1(6) . . ? C48 C47 C50 124.5(6) . . ? C49 C48 C47 125.3(6) . . ? C49 C48 H48 117.3 . . ? C47 C48 H48 117.3 . . ? C48 C49 C44 121.7(6) . . ? C48 C49 H49 119.2 . . ? C44 C49 H49 119.2 . . ? C51 C50 C55 113.8(8) . . ? C51 C50 C47 123.9(6) . . ? C55 C50 C47 122.1(6) . . ? C52 C51 C50 123.5(7) . . ? C52 C51 H51 118.2 . . ? C50 C51 H51 118.2 . . ? C51 C52 C53 123.3(7) . . ? C51 C52 H52 118.3 . . ? C53 C52 H52 118.4 . . ? C52 C53 C54 112.9(7) . . ? C52 C53 C57 123.8(6) . . ? C54 C53 C57 123.3(6) . . ? C55 C54 C53 124.7(6) . . ? C55 C54 H54 117.6 . . ? C53 C54 H54 117.6 . . ? C54 C55 C50 121.6(7) . . ? C54 C55 H55 119.2 . . ? C50 C55 H55 119.2 . . ? N39 C56 C57 178.9(9) . . ? C56 C57 C58 115.4(8) . . ? C56 C57 C53 120.8(6) . . ? C58 C57 C53 123.8(6) . . ? N40 C58 C57 179.2(10) . . ? N59 C61 C62 177.3(5) . . ? C61 C62 C61 115.8(5) 2 . ? C61 C62 C63 122.1(3) 2 . ? C61 C62 C63 122.1(3) . . ? C64 C63 C64 116.0(5) 2 . ? C64 C63 C62 122.0(3) 2 . ? C64 C63 C62 122.0(3) . . ? C63 C64 C65 122.6(4) . . ? C63 C64 H64 118.7 . . ? C65 C64 H64 118.7 . . ? C64 C65 C66 120.3(4) . . ? C64 C65 H65 119.9 . . ? C66 C65 H65 119.9 . . ? C65 C66 C65 118.2(5) 2 . ? C65 C66 C67 120.9(3) 2 . ? C65 C66 C67 120.9(3) . . ? C68 C67 C68 115.5(5) 2 . ? C68 C67 C66 122.3(3) 2 . ? C68 C67 C66 122.3(3) . . ? C69 C68 C67 122.3(4) . . ? C69 C68 H68 118.9 . . ? C67 C68 H68 118.9 . . ? C68 C69 C71 121.8(5) . . ? C68 C69 H69 119.1 . . ? C71 C69 H69 119.1 . . ? C72 C70 C72 118.9(6) 2 . ? C72 C70 C71 120.5(3) 2 . ? C72 C70 C71 120.5(3) . . ? C69 C71 C69 116.3(6) 2 . ? C69 C71 C70 121.8(3) 2 . ? C69 C71 C70 121.8(3) . . ? N60 C72 C70 176.9(6) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.25 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.504 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.137 #===END data_(3,3,5,5-TMB)(H2TCNDQ)2 _database_code_CSD 172690 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(3,3,5,5-TMB)(H2TCNDQ)2' _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 N2, 2(C18 H10 N4)' _chemical_formula_sum 'C52 H40 N10' _chemical_formula_weight 804.94 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' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5200(18) _cell_length_b 10.638(2) _cell_length_c 14.505(3) _cell_angle_alpha 111.515(11) _cell_angle_beta 97.681(13) _cell_angle_gamma 92.765(10) _cell_volume 1063.9(4) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 0 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 422 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Mac Science DIP-2020K' _diffrn_measurement_method 'theta/2theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3853 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.13 _reflns_number_total 3853 _reflns_number_gt 2898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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 full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.4107P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom (C-H) / difmap (N-H)' _refine_ls_hydrogen_treatment 'noref (C-H) / refall (N-H)' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3853 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 N1 N 0.2226(3) 0.78309(18) 0.17398(14) 0.0511(4) Uani 1 1 d . . . H1A H 0.135(3) 0.742(2) 0.1196(17) 0.050 Uiso 1 1 d . . . H1B H 0.312(3) 0.831(2) 0.1647(17) 0.050 Uiso 1 1 d . . . C2 C 0.1572(3) 0.84675(18) 0.26460(13) 0.0418(4) Uani 1 1 d . . . C3 C 0.2686(3) 0.94871(19) 0.34625(14) 0.0429(4) Uani 1 1 d . . . C4 C 0.2047(3) 1.00631(18) 0.43683(14) 0.0430(4) Uani 1 1 d . . . H4 H 0.2817 1.0761 0.4917 0.050 Uiso 1 1 calc R . . C5 C 0.0339(3) 0.96749(17) 0.45171(13) 0.0388(4) Uani 1 1 d . . . C6 C -0.0708(3) 0.86366(19) 0.36932(13) 0.0427(4) Uani 1 1 d . . . H6 H -0.1882 0.8329 0.3768 0.050 Uiso 1 1 calc R . . C7 C -0.0136(3) 0.80284(18) 0.27730(13) 0.0434(5) Uani 1 1 d . . . C8 C -0.1367(3) 0.6921(2) 0.19274(16) 0.0612(6) Uani 1 1 d . . . H8A H -0.2348 0.6625 0.2186 0.050 Uiso 1 1 calc R . . H8B H -0.0701 0.6168 0.1630 0.050 Uiso 1 1 calc R . . H8C H -0.1836 0.7265 0.1428 0.050 Uiso 1 1 calc R . . C9 C 0.4534(3) 0.9959(2) 0.33483(17) 0.0580(6) Uani 1 1 d . . . H9A H 0.4421 1.0429 0.2894 0.050 Uiso 1 1 calc R . . H9B H 0.5191 0.9188 0.3087 0.050 Uiso 1 1 calc R . . H9C H 0.5170 1.0561 0.3991 0.050 Uiso 1 1 calc R . . C10 C 0.0214(3) 0.55331(19) 0.55160(14) 0.0433(5) Uani 1 1 d . . . C11 C 0.0331(4) 0.6909(2) 0.56902(16) 0.0697(7) Uani 1 1 d . . . H11 H 0.0143 0.7182 0.5126 0.050 Uiso 1 1 calc R . . C12 C 0.0708(4) 0.7904(2) 0.66490(16) 0.0685(7) Uani 1 1 d . . . H12 H 0.0780 0.8847 0.6739 0.050 Uiso 1 1 calc R . . C13 C 0.0979(3) 0.7544(2) 0.74709(14) 0.0456(5) Uani 1 1 d . . . C14 C 0.0898(3) 0.6190(2) 0.73236(15) 0.0517(5) Uani 1 1 d . . . H14 H 0.1108 0.5926 0.7892 0.050 Uiso 1 1 calc R . . C15 C 0.0517(3) 0.5199(2) 0.63604(15) 0.0523(5) Uani 1 1 d . . . H15 H 0.0461 0.4258 0.6276 0.050 Uiso 1 1 calc R . . C16 C 0.1286(3) 0.8622(2) 0.85446(15) 0.0491(5) Uani 1 1 d . . . H16 H 0.1685 0.8191 0.9001 0.050 Uiso 1 1 calc R . . C17 C 0.2661(3) 0.9746(3) 0.86936(17) 0.0607(6) Uani 1 1 d . . . C18 C -0.0429(3) 0.9174(2) 0.87862(16) 0.0530(5) Uani 1 1 d . . . N19 N 0.3723(4) 1.0598(3) 0.87836(19) 0.0914(8) Uani 1 1 d . . . N20 N -0.1779(3) 0.9565(2) 0.89455(17) 0.0755(6) Uani 1 1 d . . . C21 C 0.5188(2) 0.50335(18) 0.55268(13) 0.0389(4) Uani 1 1 d . . . C22 C 0.5389(4) 0.6252(2) 0.63409(15) 0.0640(7) Uani 1 1 d . . . H22 H 0.5295 0.7080 0.6223 0.050 Uiso 1 1 calc R . . C23 C 0.5722(4) 0.6319(2) 0.73209(15) 0.0628(7) Uani 1 1 d . . . H23 H 0.5839 0.7184 0.7868 0.050 Uiso 1 1 calc R . . C24 C 0.5884(3) 0.51615(19) 0.75154(13) 0.0410(4) Uani 1 1 d . . . C25 C 0.5710(4) 0.3939(2) 0.67215(16) 0.0634(7) Uani 1 1 d . . . H25 H 0.5824 0.3117 0.6844 0.050 Uiso 1 1 calc R . . C26 C 0.5368(4) 0.3881(2) 0.57412(15) 0.0661(7) Uani 1 1 d . . . H26 H 0.5254 0.3014 0.5197 0.050 Uiso 1 1 calc R . . C27 C 0.6266(3) 0.5211(2) 0.85948(14) 0.0455(5) Uani 1 1 d . . . H27 H 0.6301 0.4296 0.8565 0.050 Uiso 1 1 calc R . . C28 C 0.8015(3) 0.5981(2) 0.91342(15) 0.0532(5) Uani 1 1 d . . . C29 C 0.4854(3) 0.5815(2) 0.91767(15) 0.0515(5) Uani 1 1 d . . . N30 N 0.9364(3) 0.6575(3) 0.95472(15) 0.0799(7) Uani 1 1 d . . . N31 N 0.3761(3) 0.6292(3) 0.96227(16) 0.0805(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 N1 0.0683(12) 0.0475(10) 0.0351(9) 0.0101(8) 0.0149(9) 0.0087(8) C2 0.0607(12) 0.0371(9) 0.0292(9) 0.0125(7) 0.0100(9) 0.0123(8) C3 0.0544(11) 0.0398(10) 0.0362(10) 0.0153(8) 0.0092(9) 0.0083(8) C4 0.0536(11) 0.0384(10) 0.0316(9) 0.0083(7) 0.0035(8) 0.0032(8) C5 0.0523(11) 0.0361(9) 0.0277(9) 0.0112(7) 0.0063(8) 0.0084(8) C6 0.0514(11) 0.0424(10) 0.0323(9) 0.0115(8) 0.0078(8) 0.0035(8) C7 0.0580(12) 0.0385(10) 0.0292(9) 0.0081(7) 0.0049(9) 0.0054(8) C8 0.0759(15) 0.0554(13) 0.0378(11) 0.0018(9) 0.0094(11) -0.0027(11) C9 0.0625(14) 0.0564(13) 0.0500(13) 0.0122(10) 0.0152(11) 0.0048(10) C10 0.0520(11) 0.0445(10) 0.0347(10) 0.0147(8) 0.0095(9) 0.0110(8) C11 0.129(2) 0.0442(12) 0.0371(11) 0.0186(9) 0.0035(13) 0.0174(13) C12 0.122(2) 0.0401(11) 0.0417(12) 0.0147(9) 0.0077(13) 0.0184(12) C13 0.0557(12) 0.0467(11) 0.0323(10) 0.0111(8) 0.0092(9) 0.0115(9) C14 0.0749(14) 0.0494(12) 0.0338(10) 0.0177(9) 0.0114(10) 0.0094(10) C15 0.0792(15) 0.0410(11) 0.0386(11) 0.0163(8) 0.0114(10) 0.0095(10) C16 0.0582(12) 0.0494(11) 0.0363(10) 0.0112(9) 0.0091(9) 0.0098(9) C17 0.0668(15) 0.0623(14) 0.0425(12) 0.0071(10) 0.0128(11) 0.0017(12) C18 0.0642(14) 0.0512(12) 0.0388(11) 0.0105(9) 0.0107(10) 0.0086(10) N19 0.0912(17) 0.0880(17) 0.0787(17) 0.0136(13) 0.0207(14) -0.0191(14) N20 0.0746(14) 0.0816(15) 0.0656(14) 0.0182(11) 0.0180(11) 0.0217(12) C21 0.0437(10) 0.0428(10) 0.0297(10) 0.0138(7) 0.0048(8) 0.0014(8) C22 0.114(2) 0.0388(11) 0.0354(11) 0.0141(9) -0.0005(12) 0.0063(11) C23 0.1080(19) 0.0421(11) 0.0303(10) 0.0082(8) 0.0004(11) 0.0070(11) C24 0.0447(10) 0.0475(10) 0.0299(9) 0.0149(8) 0.0023(8) 0.0030(8) C25 0.111(2) 0.0415(11) 0.0388(11) 0.0178(9) 0.0071(12) 0.0113(12) C26 0.122(2) 0.0388(11) 0.0316(10) 0.0083(8) 0.0056(12) 0.0102(12) C27 0.0538(12) 0.0507(11) 0.0319(10) 0.0165(8) 0.0044(9) 0.0045(9) C28 0.0492(12) 0.0787(15) 0.0328(10) 0.0227(10) 0.0042(9) 0.0089(11) C29 0.0485(12) 0.0673(14) 0.0337(11) 0.0163(9) 0.0012(9) -0.0035(10) N30 0.0534(12) 0.132(2) 0.0474(12) 0.0297(12) 0.0014(10) -0.0021(13) N31 0.0595(13) 0.118(2) 0.0508(12) 0.0157(12) 0.0140(10) 0.0076(12) _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 N1 C2 1.407(2) . ? N1 H1A 0.91(2) . ? N1 H1B 0.88(2) . ? C2 C7 1.404(3) . ? C2 C3 1.409(3) . ? C3 C4 1.392(3) . ? C3 C9 1.506(3) . ? C4 C5 1.398(3) . ? C4 H4 0.9600 . ? C5 C6 1.402(3) . ? C5 C5 1.488(3) 2_576 ? C6 C7 1.390(3) . ? C6 H6 0.9600 . ? C7 C8 1.510(3) . ? C8 H8A 0.9599 . ? C8 H8B 0.9599 . ? C8 H8C 0.9599 . ? C9 H9A 0.9599 . ? C9 H9B 0.9599 . ? C9 H9C 0.9599 . ? C10 C11 1.387(3) . ? C10 C15 1.390(3) . ? C10 C10 1.491(4) 2_566 ? C11 C12 1.386(3) . ? C11 H11 0.9600 . ? C12 C13 1.374(3) . ? C12 H12 0.9600 . ? C13 C14 1.374(3) . ? C13 C16 1.537(3) . ? C14 C15 1.389(3) . ? C14 H14 0.9600 . ? C15 H15 0.9600 . ? C16 C18 1.475(3) . ? C16 C17 1.475(3) . ? C16 H16 0.9600 . ? C17 N19 1.137(3) . ? C18 N20 1.136(3) . ? C21 C26 1.379(3) . ? C21 C22 1.382(3) . ? C21 C21 1.491(3) 2_666 ? C22 C23 1.385(3) . ? C22 H22 0.9600 . ? C23 C24 1.368(3) . ? C23 H23 0.9600 . ? C24 C25 1.371(3) . ? C24 C27 1.535(2) . ? C25 C26 1.389(3) . ? C25 H25 0.9600 . ? C26 H26 0.9600 . ? C27 C29 1.470(3) . ? C27 C28 1.471(3) . ? C27 H27 0.9600 . ? C28 N30 1.134(3) . ? C29 N31 1.137(3) . ? 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 N1 H1A 114.3(14) . . ? C2 N1 H1B 114.3(15) . . ? H1A N1 H1B 115(2) . . ? C7 C2 N1 120.60(18) . . ? C7 C2 C3 119.23(17) . . ? N1 C2 C3 120.00(19) . . ? C4 C3 C2 119.26(18) . . ? C4 C3 C9 120.58(18) . . ? C2 C3 C9 120.16(17) . . ? C3 C4 C5 123.18(17) . . ? C3 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? C4 C5 C6 115.69(17) . . ? C4 C5 C5 122.5(2) . 2_576 ? C6 C5 C5 121.8(2) . 2_576 ? C7 C6 C5 123.44(19) . . ? C7 C6 H6 118.3 . . ? C5 C6 H6 118.3 . . ? C6 C7 C2 119.16(17) . . ? C6 C7 C8 119.53(19) . . ? C2 C7 C8 121.30(17) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 116.25(18) . . ? C11 C10 C10 122.2(2) . 2_566 ? C15 C10 C10 121.5(2) . 2_566 ? C12 C11 C10 122.4(2) . . ? C12 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 118.95(18) . . ? C12 C13 C16 121.27(18) . . ? C14 C13 C16 119.73(18) . . ? C13 C14 C15 120.60(19) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 121.68(19) . . ? C14 C15 H15 119.2 . . ? C10 C15 H15 119.2 . . ? C18 C16 C17 109.35(19) . . ? C18 C16 C13 109.61(17) . . ? C17 C16 C13 112.85(18) . . ? C18 C16 H16 108.3 . . ? C17 C16 H16 108.3 . . ? C13 C16 H16 108.3 . . ? N19 C17 C16 178.3(3) . . ? N20 C18 C16 177.7(2) . . ? C26 C21 C22 116.36(18) . . ? C26 C21 C21 121.7(2) . 2_666 ? C22 C21 C21 121.9(2) . 2_666 ? C21 C22 C23 122.13(19) . . ? C21 C22 H22 118.9 . . ? C23 C22 H22 118.9 . . ? C24 C23 C22 120.47(19) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 118.64(18) . . ? C23 C24 C27 121.42(17) . . ? C25 C24 C27 119.94(18) . . ? C24 C25 C26 120.50(19) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 121.90(19) . . ? C21 C26 H26 119.1 . . ? C25 C26 H26 119.1 . . ? C29 C27 C28 108.43(17) . . ? C29 C27 C24 112.10(16) . . ? C28 C27 C24 111.85(16) . . ? C29 C27 H27 108.1 . . ? C28 C27 H27 108.1 . . ? C24 C27 H27 108.1 . . ? N30 C28 C27 179.8(2) . . ? N31 C29 C27 179.3(3) . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 26.13 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 0.180 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.041 #===END data_(phenazine)(H2TCNDQ) _database_code_CSD 172691 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '(phenazine)(H2TCNDQ)' _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N2, C18 H10 N4' _chemical_formula_sum 'C30 H18 N6' _chemical_formula_weight 462.50 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' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P-1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0730(12) _cell_length_b 7.3380(9) _cell_length_c 12.674(3) _cell_angle_alpha 74.474(11) _cell_angle_beta 89.585(10) _cell_angle_gamma 65.920(10) _cell_volume 574.74(17) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 0 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'Plate' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Mac Science DIP-2020K' _diffrn_measurement_method 'theta/2theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2147 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 26.44 _reflns_number_total 2147 _reflns_number_gt 1380 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_data_collection 'MXC(MAC Science)' _computing_cell_refinement 'MXC(MAC Science)' _computing_data_reduction 'Crystan' _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III' _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^)+(0.0459P)^2^+0.2908P] 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 2147 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0969 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 N1 N 0.6744(3) 0.5267(3) 1.03594(19) 0.0559(6) Uani 1 1 d . . . C2 C 0.4252(6) 0.4724(5) 1.2855(3) 0.0800(10) Uani 1 1 d . . . H2 H 0.4444 0.4730 1.3603 0.050 Uiso 1 1 calc R . . C3 C 0.5639(5) 0.4961(4) 1.2162(2) 0.0677(8) Uani 1 1 d . . . H3 H 0.6825 0.5108 1.2422 0.050 Uiso 1 1 calc R . . C4 C 0.5359(4) 0.4995(4) 1.1043(2) 0.0513(6) Uani 1 1 d . . . C5 C 0.6394(4) 0.5272(4) 0.9317(2) 0.0518(6) Uani 1 1 d . . . C6 C 0.7809(5) 0.5521(4) 0.8550(3) 0.0688(8) Uani 1 1 d . . . H6 H 0.9009 0.5681 0.8779 0.050 Uiso 1 1 calc R . . C7 C 0.7472(6) 0.5533(5) 0.7504(3) 0.0817(11) Uani 1 1 d . . . H7 H 0.8431 0.5721 0.6992 0.050 Uiso 1 1 calc R . . C8 C 0.4024(4) 0.1065(5) 0.5975(2) 0.0558(7) Uani 1 1 d . . . C9 C 0.2228(4) 0.0564(4) 0.61493(19) 0.0486(6) Uani 1 1 d . . . H9 H 0.2625 -0.0792 0.6052 0.050 Uiso 1 1 calc R . . C10 C 0.0505(4) 0.2042(5) 0.5287(2) 0.0568(7) Uani 1 1 d . . . C11 C 0.1571(4) 0.0440(4) 0.73093(18) 0.0431(6) Uani 1 1 d . . . C12 C 0.2680(4) 0.0644(5) 0.8118(2) 0.0569(7) Uani 1 1 d . . . H12 H 0.3893 0.0901 0.7958 0.050 Uiso 1 1 calc R . . C13 C 0.2058(4) 0.0479(5) 0.9168(2) 0.0585(7) Uani 1 1 d . . . H13 H 0.2846 0.0640 0.9722 0.050 Uiso 1 1 calc R . . C14 C 0.0331(3) 0.0089(3) 0.94370(17) 0.0393(5) Uani 1 1 d . . . C15 C -0.0737(4) -0.0136(4) 0.8607(2) 0.0547(7) Uani 1 1 d . . . H15 H -0.1936 -0.0420 0.8763 0.050 Uiso 1 1 calc R . . C16 C -0.0136(4) 0.0034(5) 0.7559(2) 0.0567(7) Uani 1 1 d . . . H16 H -0.0914 -0.0132 0.7003 0.050 Uiso 1 1 calc R . . N17 N 0.5445(4) 0.1419(5) 0.5833(2) 0.0785(8) Uani 1 1 d . . . N18 N -0.0821(4) 0.3144(5) 0.4613(2) 0.0863(9) 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 N1 0.0548(13) 0.0519(13) 0.0610(14) -0.0120(10) -0.0018(11) -0.0251(11) C2 0.102(3) 0.065(2) 0.0501(18) -0.0107(14) 0.0054(18) -0.0164(19) C3 0.076(2) 0.0579(18) 0.0563(18) -0.0123(13) -0.0104(15) -0.0184(16) C4 0.0535(15) 0.0398(13) 0.0525(15) -0.0071(11) -0.0049(12) -0.0156(12) C5 0.0526(15) 0.0418(14) 0.0557(16) -0.0054(11) 0.0017(12) -0.0201(12) C6 0.0664(18) 0.0591(18) 0.075(2) -0.0061(15) 0.0128(16) -0.0289(15) C7 0.092(2) 0.061(2) 0.068(2) -0.0009(15) 0.0285(19) -0.0207(18) C8 0.0499(15) 0.081(2) 0.0404(14) -0.0215(13) 0.0084(11) -0.0289(14) C9 0.0498(14) 0.0596(16) 0.0387(13) -0.0165(11) 0.0070(11) -0.0239(12) C10 0.0556(16) 0.0802(19) 0.0403(14) -0.0135(13) 0.0085(12) -0.0366(15) C11 0.0432(13) 0.0478(14) 0.0369(12) -0.0119(10) 0.0054(10) -0.0180(11) C12 0.0573(16) 0.090(2) 0.0436(15) -0.0240(14) 0.0140(12) -0.0479(16) C13 0.0626(16) 0.092(2) 0.0422(14) -0.0257(14) 0.0086(12) -0.0497(16) C14 0.0407(12) 0.0403(12) 0.0347(12) -0.0093(9) 0.0035(9) -0.0158(10) C15 0.0495(14) 0.0841(19) 0.0451(15) -0.0231(13) 0.0097(11) -0.0397(14) C16 0.0536(15) 0.092(2) 0.0407(14) -0.0260(13) 0.0057(11) -0.0416(15) N17 0.0648(16) 0.126(2) 0.0604(16) -0.0335(15) 0.0169(13) -0.0518(17) N18 0.0696(17) 0.122(2) 0.0522(15) 0.0001(15) -0.0059(13) -0.0412(17) _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 N1 C4 1.344(3) . ? N1 C5 1.345(3) . ? C2 C3 1.345(5) . ? C2 C7 1.404(5) 2_667 ? C2 H2 0.9600 . ? C3 C4 1.425(4) . ? C3 H3 0.9600 . ? C4 C5 1.427(4) 2_667 ? C5 C6 1.421(4) . ? C5 C4 1.427(4) 2_667 ? C6 C7 1.347(5) . ? C6 H6 0.9600 . ? C7 C2 1.404(5) 2_667 ? C7 H7 0.9600 . ? C8 N17 1.138(3) . ? C8 C9 1.460(4) . ? C9 C10 1.470(4) . ? C9 C11 1.529(3) . ? C9 H9 0.9600 . ? C10 N18 1.134(3) . ? C11 C12 1.370(3) . ? C11 C16 1.373(3) . ? C12 C13 1.388(3) . ? C12 H12 0.9600 . ? C13 C14 1.385(3) . ? C13 H13 0.9600 . ? C14 C15 1.382(3) . ? C14 C14 1.487(4) 2_557 ? C15 C16 1.380(3) . ? C15 H15 0.9600 . ? C16 H16 0.9600 . ? 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 C4 N1 C5 116.5(2) . . ? C3 C2 C7 120.6(3) . 2_667 ? C3 C2 H2 119.7 . . ? C7 C2 H2 119.7 2_667 . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N1 C4 C3 119.5(3) . . ? N1 C4 C5 121.8(2) . 2_667 ? C3 C4 C5 118.7(3) . 2_667 ? N1 C5 C6 119.7(3) . . ? N1 C5 C4 121.7(2) . 2_667 ? C6 C5 C4 118.6(3) . 2_667 ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C2 121.4(3) . 2_667 ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 2_667 . ? N17 C8 C9 178.6(3) . . ? C8 C9 C10 109.3(2) . . ? C8 C9 C11 113.8(2) . . ? C10 C9 C11 112.4(2) . . ? C8 C9 H9 107.0 . . ? C10 C9 H9 107.0 . . ? C11 C9 H9 107.0 . . ? N18 C10 C9 178.4(3) . . ? C12 C11 C16 119.0(2) . . ? C12 C11 C9 122.0(2) . . ? C16 C11 C9 119.0(2) . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 121.8(2) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C15 C14 C13 116.5(2) . . ? C15 C14 C14 121.9(3) . 2_557 ? C13 C14 C14 121.6(3) . 2_557 ? C16 C15 C14 122.2(2) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C11 C16 C15 120.3(2) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 26.44 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 0.159 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.040 #===END