# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1460 data_6.1a _publ_section_exptl_refinement ; Unit cell dimensions were determined from 27 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 30 seconds exposure. A full sphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Data were truncated at 24.7\%. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _publ_section_references ; Siemens (1995a). SHELXTL. Version 5.03 Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Siemens (1995b). SMART and SAINT Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _audit_creation_method SHELXL _chemical_name_systematic ; 7,7,8,8-Tetracyano-p-quinodimethane - bis(Benzene-1,2-dithiolato) -diborane adduct, form A ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'B S2 C6 H4 ^.^ TCNQ' _chemical_formula_analytical ? _chemical_formula_sum 'C24 H12 B2 N4 S4' _chemical_formula_weight 506.24 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.803(3) _cell_length_b 7.855(4) _cell_length_c 9.867(4) _cell_angle_alpha 73.85(5) _cell_angle_beta 85.71(3) _cell_angle_gamma 83.18(3) _cell_volume 576.3(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 5 _cell_measurement_theta_max 50 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method ? _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 0.434 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4904 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.70 _reflns_number_total 1963 _reflns_number_observed 1324 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 6 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.0000P] where P=(Max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0101(31) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1957 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_obs 0.0470 _refine_ls_wR_factor_all 0.1125 _refine_ls_wR_factor_obs 0.0979 _refine_ls_goodness_of_fit_all 0.982 _refine_ls_goodness_of_fit_obs 1.064 _refine_ls_restrained_S_all 0.985 _refine_ls_restrained_S_obs 1.064 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.29235(11) 0.92302(12) 0.05586(11) 0.0338(3) Uani 1 d . . C1 C 0.3521(4) 0.6938(4) 0.1189(3) 0.0264(8) Uani 1 d . . N1 N 0.4540(4) -0.1641(4) 0.4229(3) 0.0375(8) Uani 1 d . . B1 B 0.0697(5) 0.9099(5) 0.0322(4) 0.0272(10) Uani 1 d . . S2 S 0.01528(11) 0.68485(12) 0.08351(10) 0.0308(3) Uani 1 d . . N2 N 0.9200(4) 0.1192(4) 0.3187(3) 0.0373(8) Uani 1 d . . C2 C 0.2223(4) 0.5809(4) 0.1318(3) 0.0252(8) Uani 1 d . . C3 C 0.2594(5) 0.3967(5) 0.1810(3) 0.0307(9) Uani 1 d . . H3A H 0.1710(5) 0.3202(5) 0.1907(3) 0.037 Uiso 1 calc R . C4 C 0.4271(5) 0.3267(5) 0.2154(4) 0.0352(9) Uani 1 d . . H4A H 0.4538(5) 0.2014(5) 0.2491(4) 0.042 Uiso 1 calc R . C5 C 0.5555(5) 0.4379(5) 0.2010(4) 0.0366(10) Uani 1 d . . H5A H 0.6702(5) 0.3880(5) 0.2239(4) 0.044 Uiso 1 calc R . C6 C 0.5199(4) 0.6200(5) 0.1539(4) 0.0337(9) Uani 1 d . . H6A H 0.6093(4) 0.6951(5) 0.1452(4) 0.040 Uiso 1 calc R . C11 C 0.9210(4) -0.6599(4) 0.5501(3) 0.0242(8) Uani 1 d . . H11A H 0.8699(4) -0.7686(4) 0.5841(3) 0.029 Uiso 1 calc R . C12 C 0.8201(4) -0.5061(4) 0.5096(3) 0.0249(8) Uani 1 d . . H12A H 0.6981(4) -0.5076(4) 0.5152(3) 0.030 Uiso 1 calc R . C13 C 0.8930(4) -0.3375(4) 0.4573(3) 0.0245(8) Uani 1 d . . C14 C 0.7878(4) -0.1793(4) 0.4148(3) 0.0233(8) Uani 1 d . . C15 C 0.8602(4) -0.0123(5) 0.3619(4) 0.0266(8) Uani 1 d . . C16 C 0.6027(5) -0.1720(4) 0.4201(4) 0.0278(8) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0169(5) 0.0262(5) 0.0544(7) -0.0038(5) -0.0065(4) -0.0007(4) C1 0.021(2) 0.027(2) 0.030(2) -0.007(2) -0.001(2) 0.002(2) N1 0.021(2) 0.036(2) 0.054(2) -0.010(2) -0.006(2) -0.0002(15) B1 0.019(2) 0.032(2) 0.030(2) -0.008(2) -0.002(2) -0.001(2) S2 0.0183(5) 0.0316(6) 0.0418(6) -0.0079(4) -0.0064(4) -0.0012(4) N2 0.030(2) 0.028(2) 0.049(2) -0.006(2) -0.002(2) 0.004(2) C2 0.019(2) 0.028(2) 0.027(2) -0.006(2) -0.0026(15) 0.001(2) C3 0.035(2) 0.029(2) 0.028(2) -0.007(2) 0.000(2) -0.005(2) C4 0.037(2) 0.030(2) 0.035(2) -0.005(2) -0.008(2) 0.006(2) C5 0.030(2) 0.042(3) 0.034(2) -0.009(2) -0.010(2) 0.014(2) C6 0.017(2) 0.037(2) 0.044(2) -0.008(2) -0.005(2) 0.005(2) C11 0.018(2) 0.023(2) 0.032(2) -0.006(2) 0.000(2) -0.006(2) C12 0.015(2) 0.027(2) 0.035(2) -0.010(2) -0.002(2) -0.003(2) C13 0.019(2) 0.024(2) 0.032(2) -0.010(2) -0.0005(15) -0.002(2) C14 0.019(2) 0.024(2) 0.027(2) -0.006(2) -0.0011(15) -0.002(2) C15 0.019(2) 0.022(2) 0.034(2) -0.003(2) -0.005(2) 0.007(2) C16 0.028(2) 0.020(2) 0.034(2) -0.005(2) -0.004(2) 0.000(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 S1 C1 1.751(4) . ? S1 B1 1.789(4) . ? S1 S1 3.582(2) 2_675 ? C1 C6 1.395(5) . ? C1 C2 1.401(5) . ? N1 C16 1.153(4) . ? N1 H11A 2.653(4) 2_646 ? B1 B1 1.681(8) 2_575 ? B1 S2 1.792(4) . ? S2 C2 1.757(3) . ? N2 C15 1.143(4) . ? N2 H3A 2.679(5) 1_655 ? C2 C3 1.394(5) . ? C3 C4 1.386(5) . ? C4 C5 1.381(5) . ? C5 C6 1.376(5) . ? C11 C12 1.339(5) . ? C11 C13 1.446(4) 2_746 ? C12 C13 1.449(5) . ? C13 C14 1.383(5) . ? C13 C11 1.446(4) 2_746 ? C14 C16 1.436(5) . ? C14 C15 1.437(5) . ? 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 C1 S1 B1 97.2(2) . . ? C1 S1 S1 100.13(12) . 2_675 ? B1 S1 S1 153.72(14) . 2_675 ? C6 C1 C2 119.3(3) . . ? C6 C1 S1 123.8(3) . . ? C2 C1 S1 116.9(3) . . ? C16 N1 H11A 164.5(3) . 2_646 ? B1 B1 S1 123.1(4) 2_575 . ? B1 B1 S2 124.7(4) 2_575 . ? S1 B1 S2 112.2(2) . . ? C2 S2 B1 97.3(2) . . ? C15 N2 H3A 154.1(3) . 1_655 ? C3 C2 C1 120.5(3) . . ? C3 C2 S2 123.2(3) . . ? C1 C2 S2 116.3(3) . . ? C4 C3 C2 119.1(3) . . ? C5 C4 C3 120.4(3) . . ? C6 C5 C4 121.0(3) . . ? C5 C6 C1 119.8(3) . . ? C12 C11 C13 120.8(3) . 2_746 ? C11 C12 C13 121.3(3) . . ? C14 C13 C11 121.1(3) . 2_746 ? C14 C13 C12 121.0(3) . . ? C11 C13 C12 117.9(3) 2_746 . ? C13 C14 C16 122.6(3) . . ? C13 C14 C15 121.0(3) . . ? C16 C14 C15 116.5(3) . . ? N2 C15 C14 178.8(4) . . ? N1 C16 C14 179.1(4) . . ? N1 C16 H12A 104.0(3) . . ? C14 C16 H12A 76.9(2) . . ? _refine_diff_density_max 0.358 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.073 #=END data_6.1b _publ_section_exptl_refinement ; Unit cell dimensions were determined from 27 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _publ_section_references ; Siemens (1995a). SHELXTL. Version 5.03 Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Siemens (1995b). SMART and SAINT Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _audit_creation_method SHELXL _chemical_name_systematic ; 7,7,8,8-Tetracyano-p-quinodimethane - bis(Benzene-1,2-dithiolato) -diborane adduct, form B ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'B S2 C6 H4 ^.^ TCNQ' _chemical_formula_analytical ? _chemical_formula_sum 'C24 H12 B2 N4 S4' _chemical_formula_weight 506.24 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.862(2) _cell_length_b 8.386(2) _cell_length_c 9.745(2) _cell_angle_alpha 71.97(3) _cell_angle_beta 72.71(2) _cell_angle_gamma 88.28(2) _cell_volume 582.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 72 _cell_measurement_theta_min 5 _cell_measurement_theta_max 50 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method ? _exptl_crystal_F_000 258 _exptl_absorpt_coefficient_mu 0.430 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6120 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2637 _reflns_number_observed 1867 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.0000P] where P=(MAx(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'see text' _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 2637 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_obs 0.0365 _refine_ls_wR_factor_all 0.0822 _refine_ls_wR_factor_obs 0.0761 _refine_ls_goodness_of_fit_all 0.914 _refine_ls_goodness_of_fit_obs 1.019 _refine_ls_restrained_S_all 0.914 _refine_ls_restrained_S_obs 1.019 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.308 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.053 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group B1 B 0.4612(3) -0.0262(3) 0.9380(3) 0.0291(5) Uani 1 d . . S1 S 0.24027(7) 0.00792(7) 0.92536(6) 0.0327(2) Uani 1 d . . S2 S 0.58749(7) -0.12680(7) 0.80561(6) 0.0334(2) Uani 1 d . . C1 C 0.2564(3) -0.0815(2) 0.7815(2) 0.0267(4) Uani 1 d . . C2 C 0.4199(3) -0.1432(2) 0.7239(2) 0.0276(4) Uani 1 d . . C3 C 0.4446(3) -0.2138(3) 0.6079(2) 0.0341(5) Uani 1 d . . H3 H 0.5563(3) -0.2546(3) 0.5676(2) 0.041 Uiso 1 calc R . C4 C 0.3036(3) -0.2234(3) 0.5526(2) 0.0368(5) Uani 1 d . . H4 H 0.3185(3) -0.2720(3) 0.4741(2) 0.044 Uiso 1 calc R . C5 C 0.1407(3) -0.1629(3) 0.6102(2) 0.0368(5) Uani 1 d . . H5 H 0.0454(3) -0.1706(3) 0.5708(2) 0.044 Uiso 1 calc R . C6 C 0.1157(3) -0.0916(2) 0.7241(2) 0.0330(5) Uani 1 d . . H6 H 0.0041(3) -0.0498(2) 0.7630(2) 0.040 Uiso 1 calc R . C11 C 0.1322(2) -0.5471(2) -0.1114(2) 0.0239(4) Uani 1 d . . H11 H 0.2196(2) -0.5793(2) -0.1873(2) 0.029 Uiso 1 calc R . C12 C 0.1813(2) -0.5036(2) -0.0064(2) 0.0248(4) Uani 1 d . . H12 H 0.3031(2) -0.5052(2) -0.0091(2) 0.030 Uiso 1 calc R . C13 C 0.0520(2) -0.4546(2) 0.1103(2) 0.0228(4) Uani 1 d . . C14 C 0.1025(2) -0.4115(2) 0.2184(2) 0.0240(4) Uani 1 d . . C15 C -0.0243(3) -0.3653(2) 0.3380(2) 0.0269(4) Uani 1 d . . C16 C 0.2844(3) -0.4099(2) 0.2196(2) 0.0259(4) Uani 1 d . . N2 N -0.1234(2) -0.3294(2) 0.4340(2) 0.0368(4) Uani 1 d . . N1 N 0.4300(2) -0.4056(2) 0.2193(2) 0.0360(4) Uani 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 B1 0.0241(12) 0.0279(12) 0.0328(13) -0.0031(10) -0.0110(10) -0.0052(9) S1 0.0264(3) 0.0367(3) 0.0443(3) -0.0206(3) -0.0163(2) 0.0036(2) S2 0.0225(3) 0.0439(3) 0.0340(3) -0.0102(3) -0.0110(2) 0.0005(2) C1 0.0271(11) 0.0248(10) 0.0305(11) -0.0087(9) -0.0117(9) -0.0023(8) C2 0.0257(10) 0.0255(10) 0.0279(11) -0.0020(9) -0.0091(9) -0.0048(8) C3 0.0351(12) 0.0337(12) 0.0289(12) -0.0069(10) -0.0059(10) 0.0013(9) C4 0.0500(15) 0.0319(12) 0.0297(12) -0.0082(10) -0.0148(11) -0.0039(10) C5 0.0425(14) 0.0324(12) 0.0420(13) -0.0077(11) -0.0257(11) -0.0038(10) C6 0.0302(12) 0.0296(11) 0.0443(13) -0.0120(10) -0.0183(10) 0.0004(9) C11 0.0180(10) 0.0264(10) 0.0248(10) -0.0069(8) -0.0040(8) 0.0010(8) C12 0.0163(9) 0.0281(10) 0.0281(11) -0.0070(9) -0.0057(8) -0.0009(8) C13 0.0181(9) 0.0218(9) 0.0264(10) -0.0061(8) -0.0052(8) -0.0013(7) C14 0.0181(10) 0.0260(10) 0.0259(11) -0.0069(9) -0.0050(8) 0.0002(8) C15 0.0246(11) 0.0303(11) 0.0290(11) -0.0093(9) -0.0129(9) 0.0004(8) C16 0.0269(11) 0.0289(10) 0.0215(10) -0.0084(9) -0.0059(9) -0.0013(8) N2 0.0328(10) 0.0452(11) 0.0366(11) -0.0179(10) -0.0116(9) 0.0067(9) N1 0.0241(10) 0.0474(11) 0.0371(11) -0.0123(9) -0.0107(8) -0.0016(8) _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 B1 B1 1.676(4) 2_657 ? B1 S1 1.786(2) . ? B1 S2 1.796(3) . ? S1 C1 1.757(2) . ? S1 H6 3.193(2) 2_557 ? S1 S1 3.6128(14) 2_557 ? S2 C2 1.759(2) . ? S2 H6 3.236(2) 1_655 ? C1 C6 1.395(3) . ? C1 C2 1.395(3) . ? C2 C3 1.393(3) . ? C3 C4 1.384(3) . ? C4 C5 1.386(3) . ? C5 C6 1.380(3) . ? C11 C12 1.343(2) . ? C11 C13 1.445(2) 2_545 ? C12 C13 1.439(3) . ? C13 C14 1.375(3) . ? C13 C11 1.445(2) 2_545 ? C14 C16 1.434(3) . ? C14 C15 1.438(3) . ? C15 N2 1.140(2) . ? C16 N1 1.145(2) . ? N2 H3 2.625(3) 1_455 ? N1 H11 2.682(3) 2_645 ? N1 H12 2.731(3) 2_645 ? 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 B1 B1 S1 123.6(2) 2_657 . ? B1 B1 S2 124.3(2) 2_657 . ? S1 B1 S2 112.11(12) . . ? C1 S1 B1 97.36(10) . . ? C1 S1 H6 146.28(8) . 2_557 ? B1 S1 H6 108.26(9) . 2_557 ? C1 S1 S1 98.93(7) . 2_557 ? B1 S1 S1 154.85(8) . 2_557 ? H6 S1 S1 50.15(4) 2_557 2_557 ? C2 S2 B1 97.24(10) . . ? C2 S2 H6 148.80(8) . 1_655 ? B1 S2 H6 106.52(8) . 1_655 ? C6 C1 C2 120.1(2) . . ? C6 C1 S1 123.1(2) . . ? C2 C1 S1 116.81(14) . . ? C3 C2 C1 120.4(2) . . ? C3 C2 S2 123.1(2) . . ? C1 C2 S2 116.47(14) . . ? C4 C3 C2 118.8(2) . . ? C3 C4 C5 120.9(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C1 119.2(2) . . ? C12 C11 C13 120.7(2) . 2_545 ? C11 C12 C13 121.0(2) . . ? C14 C13 C12 120.8(2) . . ? C14 C13 C11 120.9(2) . 2_545 ? C12 C13 C11 118.3(2) . 2_545 ? C13 C14 C16 122.4(2) . . ? C13 C14 C15 122.0(2) . . ? C16 C14 C15 115.6(2) . . ? N2 C15 C14 179.1(2) . . ? N1 C16 C14 178.8(2) . . ? C15 N2 H3 151.6(2) . 1_455 ? C15 N2 H5 111.8(2) . . ? H3 N2 H5 94.24(9) 1_455 . ? C16 N1 H11 171.2(2) . 2_645 ? C16 N1 H12 121.5(2) . 2_645 ? H11 N1 H12 49.83(6) 2_645 2_645 ? C16 N1 H4 88.96(15) . . ? H11 N1 H4 99.73(8) 2_645 . ? H12 N1 H4 149.40(9) 2_645 . ? #=END data_6.2 _publ_section_exptl_refinement ; Unit cell dimensions were determined from 42 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _publ_section_references ; Siemens (1995a). SHELXTL. Version 5.03 Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Siemens (1995b). SMART and SAINT Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _audit_creation_method SHELXL _chemical_name_systematic ; tetracyanoethene - bis(Benzene-1,2-dithiolato) -diborane adduct ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'B S2 C6 H4 ^.^ TCNE' _chemical_formula_analytical ? _chemical_formula_sum 'C18 H8 B2 N4 S4' _chemical_formula_weight 430.14 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.861(3) _cell_length_b 7.172(3) _cell_length_c 10.862(3) _cell_angle_alpha 80.80(2) _cell_angle_beta 79.61(3) _cell_angle_gamma 64.00(2) _cell_volume 470.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 5 _cell_measurement_theta_max 50 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method ? _exptl_crystal_F_000 218 _exptl_absorpt_coefficient_mu 0.517 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4889 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2123 _reflns_number_observed 1523 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.0000P] where P=(Max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0197(54) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2123 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_obs 0.0470 _refine_ls_wR_factor_all 0.1211 _refine_ls_wR_factor_obs 0.1156 _refine_ls_goodness_of_fit_all 0.967 _refine_ls_goodness_of_fit_obs 1.101 _refine_ls_restrained_S_all 0.967 _refine_ls_restrained_S_obs 1.101 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group B1 B 0.5137(5) 0.3854(5) 0.0403(3) 0.0215(7) Uani 1 d . . S1 S 0.76867(12) 0.18956(11) 0.08499(7) 0.0234(2) Uani 1 d . . S2 S 0.29305(12) 0.31045(11) 0.08972(6) 0.0233(2) Uani 1 d . . C1 C 0.6712(5) 0.0043(4) 0.1569(2) 0.0191(6) Uani 1 d . . C2 C 0.4473(5) 0.0624(4) 0.1605(2) 0.0194(6) Uani 1 d . . C3 C 0.3562(5) -0.0751(4) 0.2170(2) 0.0233(6) Uani 1 d . . H3A H 0.2038(5) -0.0352(4) 0.2209(2) 0.028 Uiso 1 calc R . C4 C 0.4914(5) -0.2713(5) 0.2676(3) 0.0260(7) Uani 1 d . . H4A H 0.4308(5) -0.3662(5) 0.3056(3) 0.031 Uiso 1 calc R . C5 C 0.7149(5) -0.3301(4) 0.2633(3) 0.0251(6) Uani 1 d . . H5A H 0.8054(5) -0.4650(4) 0.2977(3) 0.030 Uiso 1 calc R . C6 C 0.8056(5) -0.1933(4) 0.2091(3) 0.0229(6) Uani 1 d . . H6A H 0.9575(5) -0.2328(4) 0.2074(3) 0.028 Uiso 1 calc R . C7 C 0.6095(5) -0.0437(4) 0.5017(2) 0.0216(6) Uani 1 d . . C8 C 0.7180(5) -0.2528(5) 0.5585(3) 0.0236(6) Uani 1 d . . C9 C 0.7353(5) 0.0724(5) 0.4498(3) 0.0248(6) Uani 1 d . . N8 N 0.7988(4) -0.4198(4) 0.6033(2) 0.0303(6) Uani 1 d . . N9 N 0.8334(4) 0.1669(4) 0.4080(2) 0.0331(6) Uani 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 B1 0.028(2) 0.020(2) 0.018(2) 0.0003(12) -0.0011(13) -0.0133(14) S1 0.0249(4) 0.0184(4) 0.0283(4) 0.0073(3) -0.0035(3) -0.0135(3) S2 0.0241(4) 0.0196(4) 0.0246(4) 0.0053(3) -0.0035(3) -0.0098(3) C1 0.026(2) 0.0172(13) 0.0172(13) 0.0028(10) -0.0011(11) -0.0137(12) C2 0.0246(15) 0.0157(13) 0.0188(13) 0.0024(10) -0.0027(11) -0.0106(11) C3 0.026(2) 0.027(2) 0.0227(14) 0.0001(12) 0.0006(12) -0.0188(13) C4 0.040(2) 0.024(2) 0.0224(14) 0.0034(12) -0.0009(13) -0.0234(14) C5 0.036(2) 0.0156(14) 0.0233(14) 0.0047(11) -0.0062(12) -0.0122(13) C6 0.025(2) 0.0208(15) 0.0243(14) 0.0024(11) -0.0038(12) -0.0117(12) C7 0.0269(15) 0.0233(15) 0.0185(13) 0.0023(11) -0.0024(11) -0.0157(13) C8 0.0216(15) 0.026(2) 0.0242(14) 0.0027(12) -0.0018(12) -0.0135(13) C9 0.024(2) 0.025(2) 0.0256(15) 0.0043(12) -0.0063(12) -0.0113(13) N8 0.0296(14) 0.0287(15) 0.0332(14) 0.0059(12) -0.0033(11) -0.0161(12) N9 0.034(2) 0.035(2) 0.0370(15) 0.0098(12) -0.0065(12) -0.0241(13) _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 B1 B1 1.682(6) 2_665 ? B1 S2 1.788(3) . ? B1 S1 1.790(3) . ? S1 C1 1.755(3) . ? S1 S1 3.578(2) 2_755 ? S2 C2 1.755(3) . ? C1 C2 1.399(4) . ? C1 C6 1.402(4) . ? C2 C3 1.396(4) . ? C3 C4 1.391(4) . ? C4 C5 1.394(4) . ? C5 C6 1.384(4) . ? C7 C7 1.356(6) 2_656 ? C7 C9 1.435(4) . ? C7 C8 1.440(4) . ? C8 N8 1.144(4) . ? C9 N9 1.145(4) . ? N8 H4A 2.624(4) 2_646 ? N9 H5A 2.658(4) 1_565 ? 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 B1 B1 S2 123.9(3) 2_665 . ? B1 B1 S1 123.4(3) 2_665 . ? S2 B1 S1 112.8(2) . . ? C1 S1 B1 96.92(15) . . ? C1 S1 S1 92.56(10) . 2_755 ? B1 S1 S1 132.61(11) . 2_755 ? C2 S2 B1 96.80(14) . . ? C2 C1 C6 120.1(3) . . ? C2 C1 S1 116.6(2) . . ? C6 C1 S1 123.3(2) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 S2 122.9(2) . . ? C1 C2 S2 116.9(2) . . ? C4 C3 C2 119.2(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C5 C4 120.4(3) . . ? C5 C6 C1 119.4(3) . . ? C7 C7 C9 120.2(3) 2_656 . ? C7 C7 C8 120.5(3) 2_656 . ? C9 C7 C8 119.3(3) . . ? N8 C8 C7 178.0(3) . . ? N9 C9 C7 179.2(3) . . ? C8 N8 H4A 121.1(2) . 2_646 ? C9 N9 H5A 144.4(2) . 1_565 ? _refine_diff_density_max 0.630 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.103 #=END data_7.1 _publ_section_exptl_refinement ; Unit cell dimensions were determined from 63 reflections taken from three sets of 50 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reiciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Data were truncated at 24.7\%. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _publ_section_references ; Siemens (1995a). SHELXTL. Version 5.03 Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Siemens (1995b). SMART and SAINT Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _audit_creation_method SHELXL _chemical_name_systematic ; 7,7,8,8-Tetracyano-p-quinodimethane - bis(Benzene-1,2-diolato) -diborane adduct ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'B O2 C6 H4 ^.^ TCNQ' _chemical_formula_analytical ? _chemical_formula_sum 'C24 H12 B2 N4 O4' _chemical_formula_weight 442.00 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1996(11) _cell_length_b 8.560(3) _cell_length_c 9.414(3) _cell_angle_alpha 67.00(2) _cell_angle_beta 83.16(2) _cell_angle_gamma 75.47(2) _cell_volume 516.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 63 _cell_measurement_theta_min 5 _cell_measurement_theta_max 50 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method ? _exptl_crystal_F_000 226 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4293 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 24.70 _reflns_number_total 1749 _reflns_number_observed 1164 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0841P)^2^+0.0000P] where P=(Max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0133(62) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1749 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_obs 0.0547 _refine_ls_wR_factor_all 0.1375 _refine_ls_wR_factor_obs 0.1322 _refine_ls_goodness_of_fit_all 0.907 _refine_ls_goodness_of_fit_obs 1.093 _refine_ls_restrained_S_all 0.907 _refine_ls_restrained_S_obs 1.093 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.5647(2) 0.7424(2) 0.6046(2) 0.0351(5) Uani 1 d . . C1 C 0.4377(4) 0.6335(3) 0.6320(3) 0.0314(6) Uani 1 d . . B1 B 0.4583(4) 0.9089(4) 0.5303(3) 0.0327(7) Uani 1 d . . N1 N 0.0674(3) -0.1140(3) 0.1912(2) 0.0405(6) Uani 1 d . . O2 O 0.2698(2) 0.9081(2) 0.5105(2) 0.0352(5) Uani 1 d . . C2 C 0.2616(4) 0.7333(3) 0.5765(3) 0.0310(6) Uani 1 d . . N2 N 0.5819(3) 0.0918(3) 0.1291(3) 0.0414(6) Uani 1 d . . C3 C 0.1065(4) 0.6617(4) 0.5847(3) 0.0387(7) Uani 1 d . . H3A H -0.0151(4) 0.7314(4) 0.5454(3) 0.046 Uiso 1 calc R . C4 C 0.1398(4) 0.4817(4) 0.6539(3) 0.0433(7) Uani 1 d . . H4A H 0.0373(4) 0.4262(4) 0.6640(3) 0.052 Uiso 1 calc R . C5 C 0.3185(4) 0.3806(4) 0.7088(3) 0.0436(8) Uani 1 d . . H5A H 0.3355(4) 0.2576(4) 0.7536(3) 0.052 Uiso 1 calc R . C6 C 0.4756(4) 0.4545(4) 0.7004(3) 0.0405(7) Uani 1 d . . H6A H 0.5981(4) 0.3863(4) 0.7390(3) 0.049 Uiso 1 calc R . C11 C 0.1970(3) 0.4711(3) 0.0221(3) 0.0279(6) Uani 1 d . . H11A H 0.3304(3) 0.4490(3) 0.0382(3) 0.033 Uiso 1 calc R . C12 C -0.0964(3) 0.3642(3) 0.0342(3) 0.0262(6) Uani 1 d . . H12A H -0.1596(3) 0.2716(3) 0.0581(3) 0.031 Uiso 1 calc R . C13 C 0.1070(3) 0.3249(3) 0.0593(3) 0.0240(6) Uani 1 d . . C14 C 0.2121(3) 0.1575(3) 0.1117(3) 0.0270(6) Uani 1 d . . C15 C 0.4175(4) 0.1197(3) 0.1232(3) 0.0287(6) Uani 1 d . . C16 C 0.1296(3) 0.0077(3) 0.1547(3) 0.0297(6) Uani 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 O1 0.0338(10) 0.0370(11) 0.0441(10) -0.0183(9) -0.0013(8) -0.0192(9) C1 0.0350(15) 0.0345(15) 0.0343(13) -0.0173(12) 0.0034(11) -0.0194(12) B1 0.034(2) 0.040(2) 0.034(2) -0.0186(14) -0.0033(13) -0.0171(15) N1 0.0423(14) 0.0316(13) 0.0534(14) -0.0146(11) -0.0050(11) -0.0191(12) O2 0.0369(11) 0.0303(10) 0.0437(10) -0.0105(8) -0.0086(8) -0.0189(8) C2 0.040(2) 0.0290(14) 0.0321(13) -0.0126(11) 0.0002(11) -0.0199(12) N2 0.0273(13) 0.0396(14) 0.066(2) -0.0258(12) -0.0026(11) -0.0114(11) C3 0.042(2) 0.048(2) 0.0397(15) -0.0183(13) -0.0015(12) -0.0306(14) C4 0.062(2) 0.048(2) 0.0368(15) -0.0183(13) 0.0036(13) -0.040(2) C5 0.072(2) 0.035(2) 0.0382(15) -0.0205(13) 0.0107(14) -0.031(2) C6 0.051(2) 0.036(2) 0.0382(14) -0.0168(12) 0.0030(12) -0.0125(13) C11 0.0213(13) 0.0341(15) 0.0385(14) -0.0187(11) -0.0018(10) -0.0154(11) C12 0.0228(13) 0.0264(15) 0.0377(13) -0.0158(11) -0.0024(10) -0.0130(11) C13 0.0229(13) 0.0255(14) 0.0312(12) -0.0137(10) -0.0014(9) -0.0130(11) C14 0.0262(13) 0.0281(14) 0.0337(13) -0.0137(11) -0.0020(10) -0.0143(11) C15 0.030(2) 0.0234(13) 0.0372(14) -0.0132(11) -0.0034(10) -0.0093(11) C16 0.0250(13) 0.0306(15) 0.0381(14) -0.0147(11) -0.0029(10) -0.0104(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 O1 B1 1.381(3) . ? O1 C1 1.399(3) . ? C1 C2 1.369(4) . ? C1 C6 1.377(4) . ? B1 O2 1.394(3) . ? B1 B1 1.677(6) 2_676 ? N1 C16 1.149(3) . ? N1 H4A 2.737(4) 2_556 ? O2 C2 1.392(3) . ? C2 C3 1.383(3) . ? N2 C15 1.151(3) . ? N2 H12A 2.572(3) 1_655 ? N2 H5A 2.684(4) 2_656 ? C3 C4 1.387(4) . ? C4 C5 1.386(4) . ? C5 C6 1.409(4) . ? C11 C12 1.337(3) 2_565 ? C11 C13 1.456(3) . ? C12 C11 1.337(3) 2_565 ? C12 C13 1.444(3) . ? C13 C14 1.364(3) . ? C14 C15 1.440(3) . ? C14 C16 1.442(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 B1 O1 C1 105.1(2) . . ? C2 C1 C6 123.2(2) . . ? C2 C1 O1 109.0(2) . . ? C6 C1 O1 127.8(2) . . ? O1 B1 O2 111.5(2) . . ? O1 B1 B1 125.2(3) . 2_676 ? O2 B1 B1 123.3(3) . 2_676 ? C16 N1 H4A 167.4(2) . 2_556 ? C2 O2 B1 104.7(2) . . ? C1 C2 C3 122.4(2) . . ? C1 C2 O2 109.7(2) . . ? C3 C2 O2 127.9(2) . . ? C15 N2 H12A 136.8(2) . 1_655 ? C15 N2 H5A 100.2(2) . 2_656 ? H12A N2 H5A 123.01(12) 1_655 2_656 ? C2 C3 C4 115.8(3) . . ? C5 C4 C3 121.8(3) . . ? C4 C5 C6 122.1(3) . . ? C1 C6 C5 114.7(3) . . ? C12 C11 C13 121.6(2) 2_565 . ? C11 C12 C13 121.0(2) 2_565 . ? C14 C13 C12 121.4(2) . . ? C14 C13 C11 121.1(2) . . ? C12 C13 C11 117.4(2) . . ? C13 C14 C15 121.1(2) . . ? C13 C14 C16 123.5(2) . . ? C15 C14 C16 115.4(2) . . ? N2 C15 C14 178.5(3) . . ? N1 C16 C14 178.4(2) . . ? _refine_diff_density_max 0.342 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.064 #=END data_7.2 _publ_section_exptl_refinement ; Unit cell dimensions were determined from 27 reflections taken from three sets of 30 frames (at 0.3\% steps in \w) each at 10 seconds exposure. A full sphere of reciprocal space was scanned by 0.3\% \w steps at \f 0, 90 and 180\% with the area detector held at 2\q = -29\%. The crystal-to-detector distance was 4.974 cm. Crystal decay was monitored by repeating the initial 50 frames at the end of data collection and analysing the duplicate reflections. No decay was observed. Hydrogen atoms were constrained to idealized geometries and assigned isotropic displacement parameters 1.2 times the U~iso~ value of their attached carbon. ; _publ_section_references ; Siemens (1995a). SHELXTL. Version 5.03 Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Siemens (1995b). SMART and SAINT Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _audit_creation_method SHELXL _chemical_name_systematic ; Tetracyanoethene - bis(Benzene-1,2-diolato) -diborane adduct ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural 'B O2 C6 H4 ^.^ TCNE' _chemical_formula_analytical ? _chemical_formula_sum 'C18 H8 B2 N4 O4' _chemical_formula_weight 365.90 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.962(3) _cell_length_b 6.024(4) _cell_length_c 12.686(6) _cell_angle_alpha 97.88(2) _cell_angle_beta 97.66(3) _cell_angle_gamma 108.91(3) _cell_volume 419.2(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 5 _cell_measurement_theta_max 50 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method ? _exptl_crystal_F_000 186 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2677 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1847 _reflns_number_observed 1508 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.3923P] where P=(Max(Fo^2^,0)+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0223(83) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1846 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_obs 0.0576 _refine_ls_wR_factor_all 0.1516 _refine_ls_wR_factor_obs 0.1298 _refine_ls_goodness_of_fit_all 1.184 _refine_ls_goodness_of_fit_obs 1.130 _refine_ls_restrained_S_all 1.186 _refine_ls_restrained_S_obs 1.130 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.394 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.066 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group B1 B 0.4977(5) 0.8958(5) 0.5382(2) 0.0291(6) Uani 1 d . . O2 O 0.6999(3) 0.8863(3) 0.60384(13) 0.0307(4) Uani 1 d . . O1 O 0.2921(3) 0.7084(3) 0.54228(13) 0.0290(4) Uani 1 d . . C1 C 0.6149(4) 0.6838(4) 0.6477(2) 0.0271(5) Uani 1 d . . C2 C 0.3693(4) 0.5763(4) 0.6106(2) 0.0267(5) Uani 1 d . . C3 C 0.2360(5) 0.3673(4) 0.6387(2) 0.0316(5) Uani 1 d . . H3 H 0.0669(5) 0.2941(4) 0.6128(2) 0.038 Uiso 1 calc R . C4 C 0.3636(5) 0.2693(4) 0.7072(2) 0.0336(6) Uani 1 d . . H4 H 0.2795(5) 0.1253(4) 0.7292(2) 0.040 Uiso 1 calc R . C5 C 0.6110(5) 0.3771(5) 0.7443(2) 0.0360(6) Uani 1 d . . H5 H 0.6917(5) 0.3041(5) 0.7907(2) 0.043 Uiso 1 calc R . C6 C 0.7449(5) 0.5896(5) 0.7155(2) 0.0328(6) Uani 1 d . . H6 H 0.9141(5) 0.6641(5) 0.7409(2) 0.039 Uiso 1 calc R . C7 C 0.5659(4) -0.3965(4) 0.9866(2) 0.0269(5) Uani 1 d . . C8 C 0.8211(4) -0.2925(4) 1.0287(2) 0.0314(5) Uani 1 d . . C9 C 0.4548(4) -0.2721(4) 0.9194(2) 0.0252(5) Uani 1 d . . N8 N 1.0236(4) -0.2109(4) 1.0614(2) 0.0465(6) Uani 1 d . . N9 N 0.3694(4) -0.1670(4) 0.8693(2) 0.0340(5) Uani 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 B1 0.0374(14) 0.0272(13) 0.0248(12) 0.0048(10) 0.0057(10) 0.0143(11) O2 0.0330(9) 0.0294(8) 0.0312(9) 0.0092(7) 0.0064(7) 0.0115(7) O1 0.0340(9) 0.0273(8) 0.0270(8) 0.0091(6) -0.0002(7) 0.0131(7) C1 0.0323(12) 0.0274(11) 0.0231(11) 0.0049(9) 0.0047(9) 0.0128(9) C2 0.0333(12) 0.0272(11) 0.0215(10) 0.0042(8) 0.0020(9) 0.0146(9) C3 0.0360(13) 0.0280(12) 0.0297(12) 0.0052(9) 0.0039(10) 0.0105(10) C4 0.0505(15) 0.0278(12) 0.0274(12) 0.0092(9) 0.0086(11) 0.0181(11) C5 0.054(2) 0.0412(14) 0.0253(11) 0.0105(10) 0.0055(11) 0.0319(12) C6 0.0349(13) 0.0422(14) 0.0260(11) 0.0053(10) 0.0002(9) 0.0223(11) C7 0.0290(11) 0.0282(11) 0.0251(11) 0.0058(9) 0.0054(9) 0.0118(9) C8 0.0287(12) 0.0296(12) 0.0372(13) 0.0143(10) 0.0026(10) 0.0102(10) C9 0.0261(11) 0.0238(10) 0.0254(11) 0.0056(8) 0.0036(8) 0.0084(9) N8 0.0304(12) 0.0476(14) 0.060(2) 0.0276(12) 0.0009(10) 0.0073(10) N9 0.0366(11) 0.0321(11) 0.0353(11) 0.0091(9) 0.0014(9) 0.0155(9) _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 B1 O1 1.384(3) . ? B1 O2 1.393(3) . ? B1 B1 1.684(5) 2_676 ? O2 C1 1.383(3) . ? O2 H3 2.685(3) 1_665 ? O1 C2 1.384(3) . ? O1 H3 2.702(3) 2_566 ? O1 O1 3.491(4) 2_566 ? C1 C2 1.379(3) . ? C1 C6 1.380(3) . ? C2 C3 1.376(3) . ? C3 C4 1.392(3) . ? C4 C5 1.389(4) . ? C5 C6 1.397(4) . ? C7 C7 1.356(5) 2_647 ? C7 C8 1.438(3) . ? C7 C9 1.440(3) . ? C8 N8 1.139(3) . ? C9 N9 1.139(3) . ? N8 H5 2.603(3) 2_757 ? N9 H6 2.763(3) 1_445 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 B1 O2 111.1(2) . . ? O1 B1 B1 124.2(3) . 2_676 ? O2 B1 B1 124.7(3) . 2_676 ? C1 O2 B1 105.0(2) . . ? C1 O2 H3 146.45(15) . 1_665 ? B1 O2 H3 107.6(2) . 1_665 ? B1 O1 C2 105.4(2) . . ? B1 O1 H3 107.72(15) . 2_566 ? C2 O1 H3 145.23(15) . 2_566 ? B1 O1 O1 157.9(2) . 2_566 ? C2 O1 O1 94.86(14) . 2_566 ? H3 O1 O1 50.91(7) 2_566 2_566 ? C2 C1 C6 122.5(2) . . ? C2 C1 O2 109.4(2) . . ? C6 C1 O2 128.1(2) . . ? C3 C2 C1 122.4(2) . . ? C3 C2 O1 128.5(2) . . ? C1 C2 O1 109.1(2) . . ? C2 C3 C4 116.1(2) . . ? C5 C4 C3 121.6(2) . . ? C4 C5 C6 122.0(2) . . ? C1 C6 C5 115.5(2) . . ? C7 C7 C8 119.9(3) 2_647 . ? C7 C7 C9 121.5(3) 2_647 . ? C8 C7 C9 118.6(2) . . ? N8 C8 C7 179.6(3) . . ? N9 C9 C7 177.5(2) . . ? C8 N8 H5 132.7(2) . 2_757 ? C9 N9 H6 126.6(2) . 1_445 ? C9 N9 H4 164.6(2) . . ? H6 N9 H4 64.46(9) 1_445 . ? C9 N9 H5 122.0(2) . . ? H6 N9 H5 108.20(10) 1_445 . ? H4 N9 H5 44.36(8) . . ? #=END