# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_email JSMILLER@CHEMISTRY.UTAH.EDU _publ_contact_author_name 'Joel Miller' _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.Miller A.M.Arif.L.N.Dawe J.Howard P.M.B.Piccoli A.J.Schultz H.A.Sparkes #Manuscript Title: [MeNC5H5]2[TCNE]2 (TCNE = tetracyanoethylene). #50-K Single Crystal X-Ray and Neutron Diffraction Characterization #of an Exceptionally Long 2.8 Å C-C Bond data_jsm039 _database_code_depnum_ccdc_archive 'CCDC 214705' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 N5' _chemical_formula_weight 222.23 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.8018(1) _cell_length_b 10.1299(3) _cell_length_c 16.5594(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.4264(17) _cell_angle_gamma 90.00 _cell_volume 1135.86(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2512 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9725 _exptl_absorpt_correction_T_max 0.9807 _exptl_absorpt_process_details 'DENSO-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL-97 input file. ; _diffrn_ambient_temperature 150(1) _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 'Nonius KappaCCD Diffractometer' _diffrn_measurement_method 'Phi plus Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4275 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2575 _reflns_number_gt 2178 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WinGX, Ortep3' _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^)+(0.0348P)^2^+0.2730P] 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 SHELXL _refine_ls_extinction_coef 0.029(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2575 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_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_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 0.08708(15) 0.52884(11) 0.20628(6) 0.0417(3) Uani 1 1 d . . . N2 N 0.27227(14) 0.78648(10) 0.01297(6) 0.0369(2) Uani 1 1 d . . . N3 N 0.35756(13) 0.46565(9) -0.12404(6) 0.0328(2) Uani 1 1 d . . . N4 N 0.21165(16) 0.21457(10) 0.08267(6) 0.0409(3) Uani 1 1 d . . . N5 N 0.69750(14) 0.31159(8) 0.27072(5) 0.0299(2) Uani 1 1 d . . . C1 C 0.12754(14) 0.54274(10) 0.14086(6) 0.0279(2) Uani 1 1 d . . . C2 C 0.17615(14) 0.55549(10) 0.05969(6) 0.0250(2) Uani 1 1 d . . . C3 C 0.22697(14) 0.68352(10) 0.03385(6) 0.0260(2) Uani 1 1 d . . . C4 C 0.21544(14) 0.44138(10) 0.01380(6) 0.0244(2) Uani 1 1 d . . . C5 C 0.29401(13) 0.45315(9) -0.06228(6) 0.0240(2) Uani 1 1 d . . . C6 C 0.21328(14) 0.31467(10) 0.05002(6) 0.0272(2) Uani 1 1 d . . . C7 C 0.51302(16) 0.35880(11) 0.27207(7) 0.0309(2) Uani 1 1 d . . . C8 C 0.46509(17) 0.43589(11) 0.33529(7) 0.0325(3) Uani 1 1 d . . . C9 C 0.60758(19) 0.46446(11) 0.39742(7) 0.0353(3) Uani 1 1 d . . . C10 C 0.79581(19) 0.41545(12) 0.39528(7) 0.0370(3) Uani 1 1 d . . . C11 C 0.83818(17) 0.33915(11) 0.33092(7) 0.0344(3) Uani 1 1 d . . . C12 C 0.7452(3) 0.22673(14) 0.20272(8) 0.0466(3) Uani 1 1 d . . . H7 H 0.4203(19) 0.3359(13) 0.2267(8) 0.038(3) Uiso 1 1 d . . . H8 H 0.334(2) 0.4715(14) 0.3346(8) 0.045(4) Uiso 1 1 d . . . H9 H 0.581(2) 0.5198(14) 0.4411(9) 0.047(4) Uiso 1 1 d . . . H10 H 0.900(2) 0.4323(14) 0.4365(9) 0.049(4) Uiso 1 1 d . . . H11 H 0.964(2) 0.3021(14) 0.3253(8) 0.042(4) Uiso 1 1 d . . . H12A H 0.782(4) 0.137(2) 0.2270(14) 0.043(8) Uiso 0.65(4) 1 d P A 1 H12B H 0.621(4) 0.226(2) 0.1603(14) 0.041(8) Uiso 0.65(4) 1 d P A 1 H12C H 0.864(4) 0.261(3) 0.1819(15) 0.044(8) Uiso 0.65(4) 1 d P A 1 H12F H 0.892(7) 0.196(5) 0.219(3) 0.045(15) Uiso 0.35(4) 1 d P A 2 H12E H 0.732(7) 0.272(4) 0.154(3) 0.039(14) Uiso 0.35(4) 1 d P A 2 H12D H 0.669(6) 0.141(4) 0.201(2) 0.034(14) Uiso 0.35(4) 1 d P A 2 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 0.0415(5) 0.0562(7) 0.0274(5) 0.0002(5) 0.0030(4) 0.0055(5) N2 0.0389(5) 0.0290(5) 0.0424(6) 0.0002(4) 0.0012(4) -0.0048(4) N3 0.0307(5) 0.0362(5) 0.0325(5) 0.0012(4) 0.0076(4) 0.0005(4) N4 0.0490(6) 0.0323(5) 0.0412(6) 0.0083(4) 0.0031(5) -0.0015(4) N5 0.0426(5) 0.0228(4) 0.0254(4) 0.0015(3) 0.0092(4) 0.0022(4) C1 0.0248(5) 0.0323(6) 0.0259(5) -0.0024(4) -0.0011(4) 0.0014(4) C2 0.0226(4) 0.0279(5) 0.0239(5) -0.0010(4) -0.0005(4) -0.0014(4) C3 0.0230(5) 0.0286(5) 0.0258(5) -0.0040(4) -0.0008(4) -0.0005(4) C4 0.0220(4) 0.0253(5) 0.0256(5) 0.0007(4) 0.0006(4) -0.0009(4) C5 0.0202(4) 0.0229(5) 0.0285(5) -0.0006(4) 0.0006(4) 0.0004(4) C6 0.0257(5) 0.0294(5) 0.0263(5) -0.0007(4) 0.0011(4) -0.0009(4) C7 0.0365(6) 0.0280(5) 0.0280(5) 0.0039(4) 0.0013(4) -0.0024(4) C8 0.0360(6) 0.0284(6) 0.0348(6) 0.0043(4) 0.0116(5) 0.0024(4) C9 0.0559(7) 0.0242(5) 0.0273(6) 0.0008(4) 0.0116(5) -0.0023(5) C10 0.0469(7) 0.0312(6) 0.0313(6) 0.0037(5) -0.0045(5) -0.0044(5) C11 0.0340(6) 0.0301(6) 0.0392(6) 0.0081(5) 0.0034(5) 0.0040(5) C12 0.0719(10) 0.0359(7) 0.0346(7) -0.0043(6) 0.0196(7) 0.0090(7) _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 C1 1.1514(14) . ? N2 C3 1.1500(14) . ? N3 C5 1.1543(13) . ? N4 C6 1.1498(14) . ? N5 C11 1.3442(15) . ? N5 C7 1.3450(14) . ? N5 C12 1.4768(14) . ? C1 C2 1.4201(14) . ? C2 C3 1.4186(14) . ? C2 C4 1.4226(14) . ? C2 C4 2.8219(13) 3_565 ? C4 C6 1.4174(14) . ? C4 C5 1.4192(14) . ? C7 C8 1.3699(16) . ? C7 H7 0.962(13) . ? C8 C9 1.3759(17) . ? C8 H8 0.960(14) . ? C9 C10 1.3767(18) . ? C9 H9 0.945(14) . ? C10 C11 1.3691(17) . ? C10 H10 0.950(15) . ? C11 H11 0.946(13) . ? C12 H12A 1.01(3) . ? C12 H12B 1.04(3) . ? C12 H12C 0.98(3) . ? C12 H12F 1.06(5) . ? C12 H12E 0.93(5) . ? C12 H12D 1.01(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N5 C7 120.91(9) . . ? C11 N5 C12 119.62(11) . . ? C7 N5 C12 119.47(11) . . ? N1 C1 C2 178.15(12) . . ? C3 C2 C1 116.99(9) . . ? C3 C2 C4 121.22(9) . . ? C1 C2 C4 120.27(9) . . ? C3 C2 C4 96.12(6) . 3_565 ? C1 C2 C4 96.57(6) . 3_565 ? C4 C2 C4 89.78(6) . 3_565 ? N2 C3 C2 178.55(11) . . ? C6 C4 C5 118.14(9) . . ? C6 C4 C2 119.99(9) . . ? C5 C4 C2 120.76(9) . . ? N3 C5 C4 178.52(11) . . ? N4 C6 C4 176.98(11) . . ? N5 C7 C8 120.35(10) . . ? N5 C7 H7 116.4(8) . . ? C8 C7 H7 123.2(8) . . ? C7 C8 C9 119.31(11) . . ? C7 C8 H8 119.5(8) . . ? C9 C8 H8 121.1(8) . . ? C8 C9 C10 119.73(11) . . ? C8 C9 H9 121.6(8) . . ? C10 C9 H9 118.6(8) . . ? C11 C10 C9 119.23(11) . . ? C11 C10 H10 117.7(9) . . ? C9 C10 H10 123.1(9) . . ? N5 C11 C10 120.47(11) . . ? N5 C11 H11 115.5(8) . . ? C10 C11 H11 124.0(8) . . ? N5 C12 H12A 106.4(12) . . ? N5 C12 H12B 107.3(12) . . ? H12A C12 H12B 114.2(18) . . ? N5 C12 H12C 108.2(13) . . ? H12A C12 H12C 106.1(19) . . ? H12B C12 H12C 114.2(18) . . ? N5 C12 H12F 104(2) . . ? H12A C12 H12F 57(2) . . ? H12B C12 H12F 148(2) . . ? H12C C12 H12F 53(2) . . ? N5 C12 H12E 111(2) . . ? H12A C12 H12E 142(3) . . ? H12B C12 H12E 54(3) . . ? H12C C12 H12E 62(3) . . ? H12F C12 H12E 112(3) . . ? N5 C12 H12D 112(2) . . ? H12A C12 H12D 49(2) . . ? H12B C12 H12D 66(2) . . ? H12C C12 H12D 137(2) . . ? H12F C12 H12D 103(3) . . ? H12E C12 H12D 113(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 178(100) . . . . ? N1 C1 C2 C4 -16(3) . . . . ? N1 C1 C2 C4 77(3) . . . 3_565 ? C1 C2 C3 N2 106(4) . . . . ? C4 C2 C3 N2 -60(4) . . . . ? C4 C2 C3 N2 -153(4) 3_565 . . . ? C3 C2 C4 C6 163.17(9) . . . . ? C1 C2 C4 C6 -2.33(14) . . . . ? C4 C2 C4 C6 -99.81(9) 3_565 . . . ? C3 C2 C4 C5 -4.52(14) . . . . ? C1 C2 C4 C5 -170.01(9) . . . . ? C4 C2 C4 C5 92.51(9) 3_565 . . . ? C6 C4 C5 N3 -173(4) . . . . ? C2 C4 C5 N3 -5(4) . . . . ? C5 C4 C6 N4 154(2) . . . . ? C2 C4 C6 N4 -14(2) . . . . ? C11 N5 C7 C8 -0.18(16) . . . . ? C12 N5 C7 C8 178.93(11) . . . . ? N5 C7 C8 C9 -0.04(16) . . . . ? C7 C8 C9 C10 0.02(16) . . . . ? C8 C9 C10 C11 0.21(17) . . . . ? C7 N5 C11 C10 0.42(16) . . . . ? C12 N5 C11 C10 -178.68(11) . . . . ? C9 C10 C11 N5 -0.44(17) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.214 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.030 # Information for phase 1 data_TCNE50_phase_1 _database_code_depnum_ccdc_archive 'CCDC 256746' _pd_block_id 2004-09-29T09:14|TCNE50_phase1|Paula_M._B._Piccoli|| #============================================================================== # 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA _pd_char_particle_morphology ? _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_melting_point ? _chemical_compound_source ? # for minerals and # natural products _symmetry_space_group_name_Hall ? _exptl_crystal_F_000 ? _exptl_crystal_density_diffrn ? _exptl_crystal_density_meas ' not measured' _exptl_crystal_density_method ? _cell_measurement_temperature ' 50 K' _cell_special_details ; ? ; _geom_special_details ? # The following item identifies the program(s) used (if appropriate). _computing_structure_solution ? #============================================================================== # 8. Phase information from GSAS _pd_phase_name '(MePy)2(TCNE)2 at 50K' _cell_length_a 6.7310(10) _cell_length_b 9.9960(20) _cell_length_c 16.489(4) _cell_angle_alpha 90.0 _cell_angle_beta 95.235(19) _cell_angle_gamma 90.0 _cell_volume 1104.8031 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 -x+1/2,+y+1/2,-z+1/2 -1 -x,-y,-z -2 +x+1/2,-y+1/2,+z+1/2 # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity N N1 0.08626(31) 0.52868(19) 0.20636(15) 1.0 Uani 0.02447 4 N N2 0.27450(29) 0.78942(17) 0.01230(15) 1.0 Uani 0.02251 4 N N3 0.35942(30) 0.46702(17) -0.12572(15) 1.0 Uani 0.02157 4 N N4 0.21468(31) 0.21293(18) 0.08246(15) 1.0 Uani 0.0256 4 N N5 0.69386(28) 0.31022(16) 0.26976(13) 1.0 Uani 0.01833 4 C C1 0.1283(4) 0.54314(23) 0.14051(20) 1.0 Uani 0.01884 4 C C2 0.1777(4) 0.55623(23) 0.05936(20) 1.0 Uani 0.01873 4 C C3 0.2278(4) 0.68493(23) 0.03351(20) 1.0 Uani 0.01858 4 C C4 0.2157(4) 0.44103(23) 0.01252(19) 1.0 Uani 0.01753 4 C C5 0.2946(4) 0.45458(23) -0.06346(20) 1.0 Uani 0.0166 4 C C6 0.2147(4) 0.31404(23) 0.04936(19) 1.0 Uani 0.01678 4 C C7 0.5081(4) 0.35736(24) 0.27123(21) 1.0 Uani 0.02022 4 C C8 0.4583(4) 0.43639(23) 0.33485(19) 1.0 Uani 0.01722 4 C C9 0.6029(4) 0.46460(23) 0.39740(20) 1.0 Uani 0.01886 4 C C10 0.7955(4) 0.41554(24) 0.39601(21) 1.0 Uani 0.02198 4 C C11 0.8372(4) 0.33831(24) 0.33015(20) 1.0 Uani 0.01921 4 C C12 0.7436(5) 0.22503(25) 0.20199(21) 1.0 Uani 0.02264 4 H H7 0.4053(9) 0.3308(6) 0.2207(5) 1.0 Uani 0.03638 4 H H8 0.3099(9) 0.4759(6) 0.3336(5) 1.0 Uani 0.03794 4 H H9 0.5688(10) 0.5309(6) 0.4473(4) 1.0 Uani 0.04107 4 H H10 0.9136(10) 0.4345(6) 0.4444(4) 1.0 Uani 0.03955 4 H H11 0.9842(8) 0.2961(6) 0.3230(5) 1.0 Uani 0.03764 4 H H12a 0.7669(14) 0.1263(6) 0.2266(5) 1.0 Uani 0.06067 4 H H12b 0.8707(14) 0.2640(8) 0.1768(7) 1.0 Uani 0.07276 4 H H12c 0.6224(14) 0.2228(8) 0.1553(6) 1.0 Uani 0.06968 4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 N1 0.0256(10) 0.0012(8) 0.0023(9) 0.0331(10) -0.0001(9) 0.0148(14) N2 0.0248(10) -0.0022(7) 0.0015(9) 0.0178(8) 0.0023(7) 0.0248(15) N3 0.0224(9) 0.0009(7) 0.0042(9) 0.0229(9) 0.0033(8) 0.0199(14) N4 0.0322(11) -0.0006(7) 0.0028(10) 0.0212(9) 0.0065(8) 0.0235(16) N5 0.0247(9) 0.0008(7) 0.0039(9) 0.0169(7) -0.0017(7) 0.0138(12) C1 0.0204(12) -0.0018(9) 0.0033(12) 0.0221(12) -0.0002(10) 0.0143(18) C2 0.0205(12) -0.0002(9) -0.0016(12) 0.0176(11) -0.0003(10) 0.0175(19) C3 0.0173(11) -0.0019(9) 0.0003(12) 0.0169(10) 0.0003(10) 0.0213(19) C4 0.0216(12) 0.0004(9) 0.0000(12) 0.0165(10) -0.0029(9) 0.0143(18) C5 0.0177(12) 0.0001(9) 0.0043(12) 0.0179(11) 0.0006(9) 0.0147(17) C6 0.0199(12) -0.0003(8) 0.0003(11) 0.0158(10) 0.0015(9) 0.0144(17) C7 0.0213(13) 0.0007(9) -0.0007(13) 0.0191(11) -0.0011(10) 0.0198(19) C8 0.0214(12) 0.0023(9) 0.0042(12) 0.0163(10) -0.0005(9) 0.0144(17) C9 0.0236(13) -0.0004(9) 0.0042(12) 0.0164(11) -0.0004(10) 0.0170(18) C10 0.0236(14) -0.0009(9) -0.0018(14) 0.0203(11) 0.0018(11) 0.0213(21) C11 0.0204(12) 0.0025(9) 0.0025(12) 0.0204(11) -0.0001(10) 0.0170(18) C12 0.0337(16) 0.0040(11) 0.0076(15) 0.0187(11) 0.0004(10) 0.0165(19) H7 0.0328(30) 0.0023(23) -0.0061(30) 0.0406(30) -0.0089(27) 0.034(5) H8 0.0290(29) 0.0123(24) 0.0056(30) 0.0461(32) -0.0057(29) 0.039(5) H9 0.059(4) 0.0086(28) 0.0037(33) 0.0415(30) -0.0157(27) 0.023(4) H10 0.049(4) -0.0080(26) -0.0148(32) 0.0414(30) -0.0082(26) 0.025(4) H11 0.0236(27) 0.0028(24) 0.0000(28) 0.0514(33) -0.0052(29) 0.037(5) H12a 0.124(7) 0.028(4) 0.022(5) 0.0297(29) 0.0011(27) 0.031(5) H12b 0.071(6) -0.018(4) 0.051(6) 0.083(5) -0.022(5) 0.072(8) H12c 0.065(5) 0.021(4) -0.012(5) 0.087(6) -0.043(5) 0.053(7) loop_ _atom_type_symbol _atom_type_number_in_cell C_ 48.0 H_ 32.0 N_ 20.0 # If you change Z, be sure to change all 3 of the following _chemical_formula_sum 'C12 H8 N5' _chemical_formula_weight 222.23 _cell_formula_units_Z 4 # MOLECULAR GEOMETRY 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 N1 C1 1.156(4) . 1_555 N N2 C3 1.1541(30) . 1_555 N N3 C5 1.158(4) . 1_555 N N4 C6 1.1486(31) . 1_555 N N5 C7 1.3387(32) . 1_555 N N5 C11 1.3511(33) . 1_555 N N5 C12 1.468(4) . 1_555 N N5 H7 2.045(6) . 1_555 N N5 H12a 2.048(6) . 1_555 N C1 N1 1.156(4) . 1_555 N C1 C2 1.414(4) . 1_555 N C2 C1 1.414(4) . 1_555 N C2 C3 1.4060(35) . 1_555 N C2 C4 1.423(4) . 1_555 N C3 N2 1.1541(30) . 1_555 N C3 C2 1.4060(35) . 1_555 N C4 C2 1.423(4) . 1_555 N C4 C5 1.411(4) . 1_555 N C4 C6 1.408(4) . 1_555 N C5 N3 1.158(4) . 1_555 N C5 C4 1.411(4) . 1_555 N C6 N4 1.1486(31) . 1_555 N C6 C4 1.408(4) . 1_555 N C7 N5 1.3387(32) . 1_555 N C7 C8 1.379(4) . 1_555 N C7 H7 1.067(7) . 1_555 N C8 C7 1.379(4) . 1_555 N C8 C9 1.381(4) . 1_555 N C8 H8 1.072(6) . 1_555 N C9 C8 1.381(4) . 1_555 N C9 C10 1.389(4) . 1_555 N C9 H9 1.097(7) . 1_555 N C10 C9 1.389(4) . 1_555 N C10 C11 1.382(4) . 1_555 N C10 H10 1.091(7) . 1_555 N C11 N5 1.3511(33) . 1_555 N C11 C10 1.382(4) . 1_555 N C11 H11 1.092(7) . 1_555 N C12 N5 1.468(4) . 1_555 N C12 H12a 1.073(7) . 1_555 N C12 H12b 1.059(11) . 1_555 N C12 H12c 1.069(11) . 1_555 N H7 N5 2.045(6) . 1_555 N H7 C7 1.067(7) . 1_555 N H8 C8 1.072(6) . 1_555 N H9 C9 1.097(7) . 1_555 N H10 C10 1.091(7) . 1_555 N H11 C11 1.092(7) . 1_555 N H12a N5 2.048(6) . 1_555 N H12a C12 1.073(7) . 1_555 N H12a H12b 1.778(12) . 1_555 N H12a H12c 1.746(12) . 1_555 N H12b C12 1.059(11) . 1_555 N H12b H12a 1.778(12) . 1_555 N H12b H12c 1.726(13) . 1_555 N H12c C12 1.069(11) . 1_555 N H12c H12a 1.746(12) . 1_555 N H12c H12b 1.726(13) . 1_555 N 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 C7 N5 C11 121.25(24) 1_555 . 1_555 N C7 N5 C12 119.76(24) 1_555 . 1_555 N C11 N5 C12 118.99(22) 1_555 . 1_555 N N1 C1 C2 178.03(26) 1_555 . 1_555 N C1 C2 C3 117.08(26) 1_555 . 1_555 N C1 C2 C4 120.55(23) 1_555 . 1_555 N C3 C2 C4 121.07(30) 1_555 . 1_555 N N2 C3 C2 178.06(27) 1_555 . 1_555 N C2 C4 C5 120.34(23) 1_555 . 1_555 N C2 C4 C6 119.18(30) 1_555 . 1_555 N C5 C4 C6 119.13(24) 1_555 . 1_555 N N3 C5 C4 179.3353(28) 1_555 . 1_555 N N4 C6 C4 177.21(33) 1_555 . 1_555 N N5 C7 C8 120.51(26) 1_555 . 1_555 N N5 C7 H7 116.0(4) 1_555 . 1_555 N C8 C7 H7 123.5(4) 1_555 . 1_555 N C7 C8 C9 118.79(25) 1_555 . 1_555 N C7 C8 H8 119.1(5) 1_555 . 1_555 N C9 C8 H8 122.1(5) 1_555 . 1_555 N C8 C9 C10 120.74(28) 1_555 . 1_555 N C8 C9 H9 120.1(4) 1_555 . 1_555 N C10 C9 H9 119.0(4) 1_555 . 1_555 N C9 C10 C11 117.83(27) 1_555 . 1_555 N C9 C10 H10 123.1(5) 1_555 . 1_555 N C11 C10 H10 119.1(5) 1_555 . 1_555 N N5 C11 C10 120.86(24) 1_555 . 1_555 N N5 C11 H11 115.6(4) 1_555 . 1_555 N C10 C11 H11 123.5(4) 1_555 . 1_555 N N5 C12 H12a 106.4(5) 1_555 . 1_555 N N5 C12 H12b 109.5(5) 1_555 . 1_555 N N5 C12 H12c 110.4(5) 1_555 . 1_555 N H12a C12 H12b 113.0(8) 1_555 . 1_555 N H12a C12 H12c 109.2(7) 1_555 . 1_555 N H12b C12 H12c 108.4(9) 1_555 . 1_555 N #--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--eof--# #Manuscript Title: [MeNC5H5]2[TCNE]2 (TCNE = tetracyanoethylene). #50-K Single Crystal X-Ray and Neutron Diffraction Characterization #of an Exceptionally Long 2.8 Å C-C Bond data_08has062 _database_code_depnum_ccdc_archive 'CCDC 700951' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N, C6 N4' _chemical_formula_sum 'C12 H8 N5' _chemical_formula_weight 222.23 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.7484(2) _cell_length_b 10.0584(3) _cell_length_c 16.5583(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.276(1) _cell_angle_gamma 90.00 _cell_volume 1119.18(6) _cell_formula_units_Z 4 _cell_measurement_temperature 50(2) _cell_measurement_reflns_used 5553 _cell_measurement_theta_min 2.372 _cell_measurement_theta_max 30.461 _exptl_crystal_description block _exptl_crystal_colour dark_red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 50(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 'Bruker SMART 1K CCD Detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18183 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 30.49 _reflns_number_total 3365 _reflns_number_gt 2830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^+0.3686P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3365 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_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_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 0.08607(13) 0.52837(9) 0.20597(5) 0.02053(18) Uani 1 1 d . . . N2 N 0.27470(13) 0.78966(8) 0.01254(5) 0.01897(17) Uani 1 1 d . . . N3 N 0.35888(12) 0.46702(8) -0.12548(5) 0.01775(17) Uani 1 1 d . . . N4 N 0.21451(13) 0.21246(8) 0.08210(5) 0.02039(18) Uani 1 1 d . . . N5 N 0.69405(12) 0.31061(8) 0.26992(5) 0.01459(16) Uani 1 1 d . . . C1 C 0.12764(13) 0.54289(9) 0.14045(6) 0.01482(18) Uani 1 1 d . . . C2 C 0.17647(13) 0.55633(9) 0.05913(5) 0.01386(17) Uani 1 1 d . . . C3 C 0.22881(13) 0.68548(9) 0.03343(5) 0.01429(17) Uani 1 1 d . . . C4 C 0.21660(13) 0.44167(9) 0.01284(5) 0.01382(17) Uani 1 1 d . . . C5 C 0.29565(13) 0.45397(8) -0.06340(5) 0.01351(17) Uani 1 1 d . . . C6 C 0.21551(13) 0.31365(9) 0.04933(5) 0.01468(17) Uani 1 1 d . . . C7 C 0.50747(14) 0.35761(9) 0.27145(6) 0.01556(18) Uani 1 1 d . . . H7 H 0.4092 0.3369 0.2285 0.019 Uiso 1 1 calc R . . C8 C 0.45851(14) 0.43578(9) 0.33517(6) 0.01608(18) Uani 1 1 d . . . H8 H 0.3272 0.4693 0.3363 0.019 Uiso 1 1 calc R . . C9 C 0.60354(15) 0.46488(9) 0.39764(6) 0.01674(18) Uani 1 1 d . . . H9 H 0.5720 0.5185 0.4419 0.020 Uiso 1 1 calc R . . C10 C 0.79485(14) 0.41525(9) 0.39510(6) 0.01766(19) Uani 1 1 d . . . H10 H 0.8953 0.4342 0.4376 0.021 Uiso 1 1 calc R . . C11 C 0.83688(14) 0.33812(9) 0.33001(6) 0.01663(18) Uani 1 1 d . . . H11 H 0.9675 0.3041 0.3275 0.020 Uiso 1 1 calc R . . C12 C 0.74420(16) 0.22490(10) 0.20218(6) 0.0205(2) Uani 1 1 d . . . H12C H 0.6321 0.2232 0.1601 0.031 Uiso 1 1 calc R . . H12A H 0.7714 0.1344 0.2222 0.031 Uiso 1 1 calc R . . H12B H 0.8623 0.2602 0.1793 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0203(4) 0.0245(4) 0.0168(4) 0.0002(3) 0.0020(3) 0.0019(3) N2 0.0201(4) 0.0165(4) 0.0203(4) -0.0006(3) 0.0016(3) -0.0014(3) N3 0.0174(4) 0.0179(4) 0.0183(4) 0.0007(3) 0.0034(3) 0.0005(3) N4 0.0228(4) 0.0177(4) 0.0208(4) 0.0021(3) 0.0025(3) -0.0009(3) N5 0.0195(4) 0.0119(3) 0.0129(3) 0.0005(3) 0.0044(3) 0.0008(3) C1 0.0133(4) 0.0141(4) 0.0168(4) -0.0014(3) -0.0001(3) 0.0004(3) C2 0.0137(4) 0.0139(4) 0.0140(4) -0.0006(3) 0.0012(3) -0.0002(3) C3 0.0135(4) 0.0160(4) 0.0133(4) -0.0022(3) 0.0009(3) 0.0006(3) C4 0.0137(4) 0.0134(4) 0.0144(4) 0.0000(3) 0.0012(3) -0.0003(3) C5 0.0124(4) 0.0108(4) 0.0171(4) -0.0006(3) 0.0001(3) 0.0003(3) C6 0.0139(4) 0.0161(4) 0.0141(4) -0.0015(3) 0.0018(3) 0.0001(3) C7 0.0174(4) 0.0140(4) 0.0152(4) 0.0016(3) 0.0016(3) -0.0009(3) C8 0.0174(4) 0.0137(4) 0.0179(4) 0.0023(3) 0.0056(3) 0.0009(3) C9 0.0245(4) 0.0125(4) 0.0139(4) 0.0006(3) 0.0055(3) -0.0016(3) C10 0.0218(4) 0.0150(4) 0.0157(4) 0.0018(3) -0.0009(3) -0.0019(3) C11 0.0166(4) 0.0143(4) 0.0191(4) 0.0029(3) 0.0020(3) 0.0011(3) C12 0.0289(5) 0.0176(4) 0.0159(4) -0.0032(3) 0.0077(4) 0.0038(4) _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 C1 1.1545(13) . ? N2 C3 1.1547(12) . ? N3 C5 1.1560(12) . ? N4 C6 1.1537(12) . ? N5 C7 1.3473(12) . ? N5 C11 1.3488(12) . ? N5 C12 1.4785(12) . ? C1 C2 1.4219(13) . ? C2 C3 1.4216(12) . ? C2 C4 1.4245(12) . ? C4 C5 1.4203(13) . ? C4 C6 1.4227(12) . ? C7 C8 1.3802(13) . ? C7 H7 0.9500 . ? C8 C9 1.3883(13) . ? C8 H8 0.9500 . ? C9 C10 1.3884(14) . ? C9 H9 0.9500 . ? C10 C11 1.3784(13) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? 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 N5 C11 121.32(8) . . ? C7 N5 C12 119.89(8) . . ? C11 N5 C12 118.78(8) . . ? N1 C1 C2 178.06(10) . . ? C3 C2 C1 117.13(8) . . ? C3 C2 C4 120.93(8) . . ? C1 C2 C4 120.31(8) . . ? N2 C3 C2 178.82(10) . . ? C5 C4 C6 118.25(8) . . ? C5 C4 C2 120.88(8) . . ? C6 C4 C2 119.71(8) . . ? N3 C5 C4 178.44(9) . . ? N4 C6 C4 177.07(10) . . ? N5 C7 C8 120.27(8) . . ? N5 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C9 119.19(9) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C10 119.70(9) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 119.00(9) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? N5 C11 C10 120.52(8) . . ? N5 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? N5 C12 H12C 109.5 . . ? N5 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? N5 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.345 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.045