Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_address A.Arrais ; Dipartimento di Scienze e Tecnologie Avanzate, Universita del Piemonte Orientale, Corso T. Borsalino 54, I-15100 Alessandria, Italy ; E.Boccaleri ; Dipartimento di Scienze e Tecnologie Avanzate, Universita del Piemonte Orientale, Corso T. Borsalino 54, I-15100 Alessandria, Italy ; M.Milanesio ; Dipartimento di Scienze e Tecnologie Avanzate, Universita del Piemonte Orientale, Corso T. Borsalino 54, I-15100 Alessandria, Italy ; G.Croce ; Dipartimento di Scienze e Tecnologie Avanzate, Universita del Piemonte Orientale, Corso T. Borsalino 54, I-15100 Alessandria, Italy ; R.Orlando ; Dipartimento di Scienze e Tecnologie Avanzate, Universita del Piemonte Orientale, Corso T. Borsalino 54, I-15100 Alessandria, Italy ; E.Diana ; Dipartimento di Chimica IFM, Universita di Torino, Via P. Giuria 7, I-10125 Torino, Italy ; _publ_contact_author_name 'Dr Eliano Diana' _publ_contact_author_address ; Chemistry Department University of Turin Via Pietro Giuria 7 Turin 10125 ITALY ; _publ_contact_author_email ELIANO.DIANA@UNITO.IT _publ_section_title ; Synthesis of Fluorene-D2h Cyano Electron Acceptors Co-Crystals: Structural and Spectroscopic Features of Charge Transfer Molecular Complexes ; data_ald4-fin _database_code_CSD 215462 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Fluorene-tetracianoquinodimethane complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H14 N4' _chemical_formula_weight 370.40 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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 11.011(3) _cell_length_b 13.105(3) _cell_length_c 6.789(1) _cell_angle_alpha 90.00 _cell_angle_beta 103.57(4) _cell_angle_gamma 90.00 _cell_volume 952.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type 'SADABS in Bruker AXS, SAINTplus NT, Version 6.02a, 1999' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker P4 diffractometer with SMART CCD camera' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4961 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0109 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 23.24 _reflns_number_total 669 _reflns_number_gt 599 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART32, Version 5.618, 2000' _computing_cell_refinement 'Bruker AXS, SMART32, Version 5.618, 2000' _computing_data_reduction 'Bruker AXS, SAINTplus NT, Version 6.02a, 1999' _computing_structure_solution 'SIR-97 (Giacovazzo, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL NT ver. 5.1 (Bruker AXS, 1998)' _computing_publication_material 'XP in SHELXTL NT ver. 5.1 (Bruker AXS, 1998)' _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^)+(0.1000P)^2^+0.9419P] 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 669 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1726 _refine_ls_wR_factor_gt 0.1668 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.6112(2) 0.16510(19) 0.3480(4) 0.0737(9) Uani 1 1 d . . . C1 C 0.9376(2) 0.09393(15) 0.4762(4) 0.0443(7) Uani 1 1 d . . . H1 H 0.8950 0.1558 0.4604 0.053 Uiso 1 1 calc R A 1 C2 C 0.8674(3) 0.0000 0.4486(5) 0.0427(9) Uani 1 2 d S . 1 C3 C 0.7400(3) 0.0000 0.3992(5) 0.0462(9) Uani 1 2 d S . 1 C4 C 0.6688(3) 0.09228(19) 0.3709(4) 0.0525(8) Uani 1 1 d . . 1 C5 C 0.8685(5) -0.0888(3) 0.9482(5) 0.0984(16) Uani 1 1 d . . 1 H5A H 0.9131 -0.1540 0.9652 0.118 Uiso 1 1 d . B 1 C6 C 0.9320(5) 0.0000 0.9732(7) 0.099(2) Uani 1 2 d S . 1 C7 C 0.6818(5) 0.0000 0.8744(7) 0.0924(17) Uani 1 2 d S . 1 H7A H 0.5949 0.0000 0.8401 0.111 Uiso 1 2 calc SR . 1 C8 C 1.0000 -0.1474(5) 1.0000 0.0520(18) Uani 0.50 2 d SP . 1 H8A H 0.9994 -0.1917 1.1143 0.062 Uiso 0.25 1 calc PR . 1 H8B H 1.0006 -0.1917 0.8857 0.062 Uiso 0.25 1 calc PR . 1 C9 C 0.7423(5) -0.0891(3) 0.8982(5) 0.0912(14) Uani 1 1 d . . 1 H9A H 0.6983 -0.1503 0.8807 0.109 Uiso 1 1 calc R . 1 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 0.0783(18) 0.0556(16) 0.088(2) 0.0047(13) 0.0202(15) 0.0131(13) C1 0.0620(14) 0.0301(13) 0.0426(15) 0.0008(9) 0.0158(14) 0.0037(9) C2 0.061(2) 0.0358(17) 0.0336(18) 0.000 0.0168(17) 0.000 C3 0.062(2) 0.0398(18) 0.0402(19) 0.000 0.0177(18) 0.000 C4 0.0592(16) 0.0457(15) 0.0537(17) 0.0009(11) 0.0155(14) 0.0033(13) C5 0.151(4) 0.110(3) 0.0422(19) 0.0206(18) 0.038(3) 0.069(3) C6 0.065(3) 0.202(7) 0.033(3) 0.000 0.017(3) 0.000 C7 0.063(3) 0.162(6) 0.051(3) 0.000 0.010(3) 0.000 C8 0.067(5) 0.046(4) 0.037(4) 0.000 -0.001(4) 0.000 C9 0.146(4) 0.081(2) 0.051(2) -0.0082(16) 0.031(2) -0.044(3) _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 1.136(3) . ? C1 C1 1.336(5) 2_756 ? C1 C2 1.442(3) . ? C2 C3 1.364(5) . ? C2 C1 1.442(3) 6 ? C3 C4 1.429(3) 6 ? C3 C4 1.429(3) . ? C5 C6 1.348(6) . ? C5 C9 1.351(7) . ? C5 C8 1.604(5) . ? C6 C5 1.348(6) 6 ? C6 C6 1.456(10) 5_757 ? C7 C9 1.336(5) 6 ? C7 C9 1.336(5) . ? C8 C5 1.604(5) 2_757 ? 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 C1 C2 121.38(16) 2_756 . ? C3 C2 C1 121.38(16) . . ? C3 C2 C1 121.38(16) . 6 ? C1 C2 C1 117.2(3) . 6 ? C2 C3 C4 122.21(17) . 6 ? C2 C3 C4 122.21(17) . . ? C4 C3 C4 115.6(3) 6 . ? N1 C4 C3 179.4(3) . . ? C6 C5 C9 120.5(4) . . ? C6 C5 C8 88.3(4) . . ? C9 C5 C8 151.2(5) . . ? C5 C6 C5 119.4(5) . 6 ? C5 C6 C6 120.3(3) . 5_757 ? C5 C6 C6 120.3(3) 6 5_757 ? C9 C7 C9 122.0(5) 6 . ? C5 C8 C5 122.7(6) 2_757 . ? C7 C9 C5 118.8(4) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 23.24 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.130 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.040 data_ald3-fin _database_code_CSD 215463 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Fluorene-tetracyanobenzene complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H12 N4' _chemical_formula_weight 344.37 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.416(9) _cell_length_b 8.074(9) _cell_length_c 8.118(9) _cell_angle_alpha 106.13(2) _cell_angle_beta 93.94(2) _cell_angle_gamma 91.53(2) _cell_volume 465.3(9) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 178 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type 'SADABS in Bruker AXS, SAINTplus NT, Version 6.02a, 1999' _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _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 'Brucker P4 diffractometer with SMART CCD camera' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3286 _diffrn_reflns_av_R_equivalents 0.2196 _diffrn_reflns_av_sigmaI/netI 0.1489 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 21.96 _reflns_number_total 1008 _reflns_number_gt 593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART32, Version 5.618, 2000' _computing_cell_refinement 'Bruker AXS, SMART32, Version 5.618, 2000' _computing_data_reduction 'Bruker AXS, SAINTplus NT, Version 6.02a, 1999' _computing_structure_solution 'SIR-97 (Giacovazzo, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL NT ver. 5.1 (Bruker AXS, 1998)' _computing_publication_material 'XP in SHELXTL NT ver. 5.1 (Bruker AXS, 1998)' _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^)+(0.2800P)^2^+0.0200P] 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 1008 _refine_ls_number_parameters 119 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1860 _refine_ls_R_factor_gt 0.1381 _refine_ls_wR_factor_ref 0.3893 _refine_ls_wR_factor_gt 0.3500 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _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 0.3592(11) 0.8075(9) 0.4894(10) 0.081(3) Uani 1 1 d . . . N2 N 0.3523(11) 0.4897(9) 0.8066(9) 0.081(3) Uani 1 1 d . . . C1 C 0.4515(10) 0.9307(8) 0.8215(9) 0.050(2) Uani 1 1 d . . . C2 C 0.4011(11) 0.8603(9) 0.6365(10) 0.061(3) Uani 1 1 d . . . C3 C 0.5068(10) 1.1079(8) 0.8895(9) 0.054(2) Uani 1 1 d . . . H3A H 0.5133 1.1782 0.8165 0.065 Uiso 1 1 calc R . . C4 C 0.4480(10) 0.8225(8) 0.9316(9) 0.052(2) Uani 1 1 d . . . C5 C 0.3946(11) 0.6340(10) 0.8608(9) 0.058(2) Uani 1 1 d . . . C6 C 0.953(4) 0.917(3) 0.919(3) 0.099(11) Uiso 0.50 1 d PD . 1 C7 C 0.8417(15) 0.6501(17) 0.6545(18) 0.106(4) Uani 1 1 d . A 1 H7A H 0.7988 0.5587 0.5610 0.127 Uiso 1 1 calc R A 1 C8 C 0.914(12) 0.752(6) 0.930(13) 0.36(6) Uiso 0.50 1 d PD . 1 C9 C 0.8669(15) 0.6254(14) 0.812(2) 0.117(5) Uani 1 1 d . A 1 H9A H 0.8488 0.5172 0.8297 0.140 Uiso 1 1 calc R A 1 C10 C 0.8805(16) 0.816(2) 0.6306(17) 0.123(5) Uani 1 1 d . A 1 H10A H 0.8630 0.8295 0.5207 0.148 Uiso 1 1 calc R A 1 C11 C 0.9382(17) 0.9448(18) 0.754(2) 0.039(4) Uiso 0.50 1 d PD A 1 C12 C 1.007(2) 1.147(2) 0.840(3) 0.083(5) Uiso 0.50 1 d PD . 1 H12A H 0.9074 1.2116 0.8157 0.100 Uiso 0.50 1 d P B 1 H12B H 1.1038 1.1669 0.7813 0.100 Uiso 0.50 1 d P C 1 C6' C 0.961(2) 0.855(3) 0.962(2) 0.059(5) Uiso 0.50 1 d P . 2 C8' C 0.926(2) 0.743(2) 0.958(2) 0.049(4) Uiso 0.50 1 d P D 2 C11' C 0.973(2) 0.958(2) 0.863(3) 0.054(4) Uiso 0.50 1 d P . 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 0.140(7) 0.065(5) 0.033(5) 0.005(4) 0.002(4) 0.001(4) N2 0.143(7) 0.031(4) 0.063(6) 0.008(3) -0.008(4) -0.005(4) C1 0.090(6) 0.037(4) 0.023(5) 0.008(3) -0.002(3) 0.013(3) C2 0.116(7) 0.034(4) 0.033(6) 0.006(4) 0.009(4) 0.011(4) C3 0.104(6) 0.037(4) 0.020(5) 0.009(3) -0.004(4) 0.001(4) C4 0.090(6) 0.030(4) 0.038(5) 0.010(4) 0.009(4) 0.013(3) C5 0.103(7) 0.043(5) 0.032(5) 0.017(4) 0.005(4) 0.009(4) C7 0.120(9) 0.100(9) 0.074(9) -0.014(8) 0.000(7) 0.006(7) C9 0.106(9) 0.070(8) 0.188(18) 0.057(9) 0.016(9) 0.028(6) C10 0.107(9) 0.199(15) 0.091(10) 0.076(11) 0.037(7) 0.046(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 N1 C2 1.167(10) . ? N2 C5 1.152(8) . ? C1 C4 1.413(11) . ? C1 C3 1.421(10) . ? C1 C2 1.468(11) . ? C3 C4 1.417(10) 2_677 ? C4 C3 1.417(10) 2_677 ? C4 C5 1.501(10) . ? C6 C8 1.390(16) . ? C6 C11 1.417(15) . ? C6 C6 1.68(5) 2_777 ? C7 C9 1.352(17) . ? C7 C10 1.428(19) . ? C8 C9 1.21(8) . ? C8 C12 1.86(10) 2_777 ? C10 C11 1.270(18) . ? C11 C12 1.64(2) . ? C12 C8 1.86(10) 2_777 ? C6' C8' 0.92(2) . ? C6' C11' 1.32(4) . ? C6' C11' 1.79(3) 2_777 ? C11' C6' 1.79(3) 2_777 ? 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 C1 C3 120.0(6) . . ? C4 C1 C2 120.3(6) . . ? C3 C1 C2 119.7(6) . . ? N1 C2 C1 178.6(8) . . ? C4 C3 C1 120.0(7) 2_677 . ? C1 C4 C3 120.0(6) . 2_677 ? C1 C4 C5 120.5(6) . . ? C3 C4 C5 119.5(6) 2_677 . ? N2 C5 C4 179.5(8) . . ? C8 C6 C11 118(5) . . ? C8 C6 C6 126(5) . 2_777 ? C11 C6 C6 116(2) . 2_777 ? C9 C7 C10 120.4(11) . . ? C9 C8 C6 127(7) . . ? C9 C8 C12 151(4) . 2_777 ? C6 C8 C12 82(4) . 2_777 ? C8 C9 C7 117(3) . . ? C11 C10 C7 122.3(13) . . ? C10 C11 C6 116.0(15) . . ? C10 C11 C12 154.2(14) . . ? C6 C11 C12 89.7(13) . . ? C11 C12 C8 126.3(16) . 2_777 ? C8' C6' C11' 141(2) . . ? C8' C6' C11' 133(2) . 2_777 ? C11' C6' C11' 85.9(17) . 2_777 ? C6' C11' C6' 94.1(17) . 2_777 ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.883 _refine_diff_density_max 0.329 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.117 data_ald2-fin _database_code_CSD 215464 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Fluorene-Tetracyanoethilene complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H10 N4' _chemical_formula_weight 294.29 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.183(4) _cell_length_b 7.300(4) _cell_length_c 8.194(5) _cell_angle_alpha 95.24(1) _cell_angle_beta 94.27(1) _cell_angle_gamma 114.63(1) _cell_volume 385.9(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type 'SADABS in Bruker AXS, SAINTplus NT, Version 6.02a, 1999' _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Brucker P4 diffractometer with SMART CCD camera' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2919 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0903 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 23.30 _reflns_number_total 1023 _reflns_number_gt 535 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS, SMART32, Version 5.618, 2000' _computing_cell_refinement 'Bruker AXS, SMART32, Version 5.618, 2000' _computing_data_reduction 'Bruker AXS, SAINTplus NT, Version 6.02a, 1999' _computing_structure_solution 'SIR-97 (Giacovazzo, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL NT ver. 5.1 (Bruker AXS, 1998)' _computing_publication_material 'XP in SHELXTL NT ver. 5.1 (Bruker AXS, 1998)' _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^)+(0.1516P)^2^+0.1707P] 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 1023 _refine_ls_number_parameters 99 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.1857 _refine_ls_R_factor_gt 0.1203 _refine_ls_wR_factor_ref 0.3342 _refine_ls_wR_factor_gt 0.2895 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.147 _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 -0.2809(11) -0.3636(10) 0.6387(8) 0.082(2) Uani 1 1 d . A 1 N2 N -0.3278(13) 0.1208(12) 0.3825(10) 0.089(3) Uani 1 1 d . B 1 C1 C -0.1024(9) -0.0400(9) 0.5026(8) 0.0480(19) Uani 1 1 d . . 1 C2 C -0.2036(12) -0.2224(11) 0.5800(9) 0.061(2) Uani 1 1 d . A 1 C3 C -0.2255(14) 0.0493(12) 0.4358(10) 0.067(2) Uani 1 1 d . B 1 C4A C 0.0204(16) 0.0920(10) 0.9526(8) 0.078(3) Uani 0.50 1 d PD . 1 C5A C -0.116(3) 0.168(3) 0.900(3) 0.082(4) Uiso 0.50 1 d PD . 1 C6A C 0.289(3) 0.039(2) 1.0159(19) 0.081(5) Uani 0.25 1 d PD . 1 H6AB H 0.3551 -0.0220 0.9385 0.122 Uiso 0.25 1 d P C 1 H6AC H 0.4044 0.1214 1.1059 0.122 Uiso 0.25 1 d P D 1 C7A C 0.305(3) 0.328(3) 0.864(2) 0.082(4) Uiso 0.50 1 d PD E 1 H7AA H 0.4443 0.3772 0.8518 0.099 Uiso 0.50 1 calc PR E 1 C8A C -0.030(3) 0.341(3) 0.819(2) 0.065(3) Uiso 0.50 1 d PD E 1 H8AA H -0.1101 0.4033 0.7782 0.079 Uiso 0.50 1 calc PR E 1 C9A C 0.186(2) 0.418(2) 0.8036(18) 0.047(3) Uiso 0.50 1 d PD E 1 H9AA H 0.2470 0.5324 0.7508 0.056 Uiso 0.50 1 calc PR E 1 C10A C 0.215(3) 0.173(5) 0.937(5) 0.102(4) Uiso 0.50 1 d PD E 1 C4B C 0.0204(16) 0.0920(10) 0.9526(8) 0.078(3) Uani 0.50 1 d PD . 2 C5B C -0.155(3) 0.109(3) 0.905(3) 0.082(4) Uiso 0.50 1 d PD . 2 C6B C 0.289(3) 0.039(2) 1.0159(19) 0.081(5) Uani 0.25 1 d PD . 2 H6AB' H 0.3551 -0.0220 0.9385 0.122 Uiso 0.25 1 d P F 2 H6AC' H 0.4044 0.1214 1.1059 0.122 Uiso 0.25 1 d P G 2 C7B C 0.237(3) 0.373(3) 0.840(2) 0.082(4) Uiso 0.50 1 d PD H 2 H7BA H 0.3656 0.4640 0.8167 0.099 Uiso 0.50 1 calc PR H 2 C8B C -0.128(3) 0.273(2) 0.8272(19) 0.065(3) Uiso 0.50 1 d PD H 2 H8BA H -0.2425 0.2972 0.7997 0.079 Uiso 0.50 1 calc PR H 2 C9B C 0.065(3) 0.409(2) 0.7855(16) 0.047(3) Uiso 0.50 1 d PD H 2 H9BA H 0.0773 0.5161 0.7265 0.056 Uiso 0.50 1 calc PR H 2 C10B C 0.233(3) 0.208(5) 0.927(5) 0.102(4) Uiso 0.50 1 d PD H 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 0.085(6) 0.068(4) 0.085(5) 0.032(4) 0.019(4) 0.019(4) N2 0.087(6) 0.099(6) 0.094(6) 0.030(4) 0.023(5) 0.046(5) C1 0.039(4) 0.054(4) 0.048(4) -0.002(3) -0.014(4) 0.022(4) C2 0.059(6) 0.054(4) 0.063(5) 0.018(4) 0.010(4) 0.016(4) C3 0.071(6) 0.070(5) 0.069(5) 0.018(4) 0.020(5) 0.035(5) C4A 0.146(10) 0.056(5) 0.025(4) -0.007(3) 0.015(4) 0.038(5) C6A 0.055(11) 0.095(12) 0.077(11) -0.008(9) 0.035(9) 0.016(9) C4B 0.146(10) 0.056(5) 0.025(4) -0.007(3) 0.015(4) 0.038(5) C6B 0.055(11) 0.095(12) 0.077(11) -0.008(9) 0.035(9) 0.016(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 N1 C2 1.121(8) . ? N2 C3 1.147(10) . ? C1 C1 1.344(12) 2_556 ? C1 C3 1.407(10) . ? C1 C2 1.455(9) . ? C4A C10A 1.296(17) . ? C4A C5A 1.377(17) . ? C4A C4A 1.547(14) 2_557 ? C5A C8A 1.406(17) . ? C5A C6A 1.75(2) 2_557 ? C6A C10A 1.470(18) . ? C6A C5A 1.75(2) 2_557 ? C7A C10A 1.272(17) . ? C7A C9A 1.366(16) . ? C8A C9A 1.436(16) . ? C5B C8B 1.357(17) . ? C5B C6B 1.37(2) 2_557 ? C7B C9B 1.422(17) . ? C7B C10B 1.447(17) . ? C8B C9B 1.416(16) . ? 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 C1 C3 121.6(8) 2_556 . ? C1 C1 C2 120.5(8) 2_556 . ? C3 C1 C2 117.9(6) . . ? N1 C2 C1 179.5(8) . . ? N2 C3 C1 179.1(9) . . ? C10A C4A C5A 124.4(13) . . ? C10A C4A C4A 107.2(13) . 2_557 ? C5A C4A C4A 128.3(14) . 2_557 ? C4A C5A C8A 114.6(15) . . ? C4A C5A C6A 82.0(11) . 2_557 ? C8A C5A C6A 163.3(15) . 2_557 ? C10A C6A C5A 120.0(13) . 2_557 ? C10A C7A C9A 116.9(17) . . ? C5A C8A C9A 117.3(15) . . ? C7A C9A C8A 121.9(15) . . ? C7A C10A C4A 124.9(18) . . ? C7A C10A C6A 132.7(18) . . ? C4A C10A C6A 102.4(14) . . ? C8B C5B C6B 144.8(17) . 2_557 ? C9B C7B C10B 126.5(18) . . ? C5B C8B C9B 124.2(16) . . ? C8B C9B C7B 115.6(15) . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.921 _refine_diff_density_max 0.257 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.052