# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cplx _audit_creation_method SHELXL-97 _chemical_name_systematic ; Naphthalene-perylene-7,7,8,8-tetracyanoquinodimethane complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12, C12 H4 N4, C10 H8' _chemical_formula_sum 'C42 H24 N4' _chemical_formula_weight 584.65 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 7.1260(14) _cell_length_b 10.736(2) _cell_length_c 10.971(2) _cell_angle_alpha 60.99(3) _cell_angle_beta 89.03(3) _cell_angle_gamma 86.86(3) _cell_volume 732.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 5694 _diffrn_reflns_av_R_equivalents 0.0663 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2704 _reflns_number_gt 1556 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0719P)^2^+0.0000P] 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 2704 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.004 _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 C6 C 0.6506(3) 0.7231(2) 0.1889(2) 0.0302(5) Uani 1 1 d . . . C3 C 0.3477(3) 1.1699(2) 0.1148(2) 0.0303(5) Uani 1 1 d . . . C13 C 0.9919(2) 0.9566(2) 0.1445(2) 0.0231(5) Uani 1 1 d . . . C10 C 0.4950(2) 0.9471(2) 0.1474(2) 0.0232(5) Uani 1 1 d . . . C21 C 0.9355(3) 0.4658(2) 0.0549(2) 0.0339(5) Uani 1 1 d . . . C4 C 0.4207(2) 1.0878(2) 0.0564(2) 0.0231(5) Uani 1 1 d . . . C5 C 0.5759(2) 0.8584(2) 0.0941(2) 0.0235(5) Uani 1 1 d . . . C16 C 1.0533(3) 0.7766(2) 0.3880(2) 0.0299(5) Uani 1 1 d . . . C8 C 0.5647(3) 0.7543(2) 0.3847(2) 0.0347(5) Uani 1 1 d . . . C7 C 0.6443(3) 0.6714(3) 0.3324(3) 0.0369(6) Uani 1 1 d . . . C2 C 0.3428(3) 1.1159(3) 0.2594(3) 0.0359(6) Uani 1 1 d . . . C11 C 0.9233(3) 1.0964(2) 0.0418(2) 0.0249(5) Uani 1 1 d . . . C12 C 1.0700(2) 0.8619(2) 0.0956(2) 0.0249(5) Uani 1 1 d . . . C15 C 0.9070(3) 1.0095(2) 0.3320(2) 0.0295(5) Uani 1 1 d . . . C9 C 0.4901(2) 0.8934(2) 0.2944(2) 0.0289(5) Uani 1 1 d . . . C14 C 0.9846(3) 0.9149(2) 0.2846(2) 0.0264(5) Uani 1 1 d . . . C1 C 0.4101(3) 0.9801(3) 0.3481(3) 0.0343(6) Uani 1 1 d . . . C19 C 0.9823(4) 0.4374(2) 0.1912(3) 0.0438(6) Uani 1 1 d . . . C18 C 0.7613(3) 0.4291(2) 0.0240(3) 0.0434(7) Uani 1 1 d . . . C20 C 1.1492(4) 0.4736(3) 0.2176(3) 0.0522(7) Uani 1 1 d . . . C17 C 0.7206(4) 0.4594(3) -0.1098(3) 0.0527(8) Uani 1 1 d . . . N1 N 0.8431(2) 1.0889(2) 0.3659(2) 0.0398(5) Uani 1 1 d . . . N2 N 1.1108(3) 0.6650(2) 0.4691(2) 0.0423(5) Uani 1 1 d . . . H1 H 0.410(3) 0.946(2) 0.448(2) 0.041(6) Uiso 1 1 d . . . H6 H 0.708(3) 0.659(2) 0.152(2) 0.032(6) Uiso 1 1 d . . . H8 H 0.565(3) 0.717(2) 0.490(2) 0.031(5) Uiso 1 1 d . . . H12 H 1.116(2) 0.760(2) 0.169(2) 0.023(5) Uiso 1 1 d . . . H11 H 0.873(3) 1.165(2) 0.072(2) 0.028(5) Uiso 1 1 d . . . H3 H 0.300(3) 1.270(2) 0.049(2) 0.033(6) Uiso 1 1 d . . . H2 H 0.288(3) 1.176(3) 0.301(2) 0.051(7) Uiso 1 1 d . . . H19 H 0.874(3) 0.386(3) 0.269(3) 0.057(7) Uiso 1 1 d . . . H17 H 0.590(4) 0.435(3) -0.130(3) 0.067(8) Uiso 1 1 d . . . H18 H 0.672(3) 0.379(3) 0.103(3) 0.050(7) Uiso 1 1 d . . . H7 H 0.695(3) 0.578(3) 0.397(2) 0.041(6) Uiso 1 1 d . . . H20 H 1.177(4) 0.453(3) 0.318(3) 0.076(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C6 0.0238(10) 0.0278(12) 0.0416(14) -0.0190(11) -0.0010(9) 0.0008(9) C3 0.0244(10) 0.0297(13) 0.0427(14) -0.0223(11) 0.0027(9) -0.0016(9) C13 0.0178(9) 0.0251(11) 0.0277(12) -0.0139(9) 0.0002(8) -0.0007(8) C10 0.0153(9) 0.0272(11) 0.0280(12) -0.0140(10) 0.0006(8) -0.0017(8) C21 0.0334(11) 0.0196(11) 0.0467(15) -0.0153(11) 0.0040(10) 0.0050(9) C4 0.0165(9) 0.0232(11) 0.0337(12) -0.0171(10) 0.0025(8) -0.0024(8) C5 0.0160(9) 0.0234(11) 0.0337(12) -0.0160(10) 0.0017(8) -0.0006(8) C16 0.0277(10) 0.0359(14) 0.0271(12) -0.0162(11) 0.0017(9) -0.0026(10) C8 0.0272(11) 0.0413(14) 0.0270(13) -0.0095(11) -0.0017(9) -0.0045(10) C7 0.0302(11) 0.0277(13) 0.0416(15) -0.0083(11) -0.0047(10) 0.0017(10) C2 0.0273(11) 0.0493(15) 0.0472(15) -0.0362(13) 0.0038(10) -0.0012(10) C11 0.0225(10) 0.0253(11) 0.0302(12) -0.0162(10) 0.0013(8) 0.0017(8) C12 0.0205(10) 0.0242(12) 0.0285(12) -0.0120(10) -0.0007(8) 0.0022(8) C15 0.0269(10) 0.0371(13) 0.0259(12) -0.0162(11) 0.0041(9) -0.0050(9) C9 0.0184(9) 0.0364(13) 0.0317(12) -0.0162(10) 0.0018(8) -0.0033(9) C14 0.0228(9) 0.0288(12) 0.0280(12) -0.0143(10) 0.0033(8) -0.0006(8) C1 0.0232(10) 0.0545(16) 0.0340(14) -0.0281(12) 0.0033(9) -0.0060(10) C19 0.0528(15) 0.0255(13) 0.0484(16) -0.0154(12) 0.0025(13) 0.0083(11) C18 0.0347(13) 0.0259(13) 0.0647(19) -0.0186(13) 0.0080(13) 0.0028(10) C20 0.0654(18) 0.0375(15) 0.0569(19) -0.0266(14) -0.0136(15) 0.0148(13) C17 0.0389(14) 0.0373(15) 0.089(2) -0.0370(16) -0.0146(15) 0.0096(11) N1 0.0400(10) 0.0472(13) 0.0381(12) -0.0256(10) 0.0068(9) -0.0006(9) N2 0.0426(11) 0.0385(13) 0.0370(12) -0.0118(10) -0.0047(9) 0.0038(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 C6 C7 1.393(3) . ? C6 C5 1.394(3) . ? C3 C4 1.395(3) . ? C3 C2 1.401(3) . ? C13 C14 1.378(3) . ? C13 C11 1.435(3) . ? C13 C12 1.445(3) . ? C10 C4 1.424(3) . ? C10 C9 1.425(3) . ? C10 C5 1.432(3) . ? C21 C19 1.415(3) . ? C21 C18 1.418(3) . ? C21 C21 1.419(4) 2_765 ? C4 C5 1.461(3) 2_675 ? C5 C4 1.461(3) 2_675 ? C16 N2 1.149(3) . ? C16 C14 1.427(3) . ? C8 C7 1.368(3) . ? C8 C9 1.411(3) . ? C2 C1 1.366(3) . ? C11 C12 1.349(3) 2_775 ? C12 C11 1.349(3) 2_775 ? C15 N1 1.153(3) . ? C15 C14 1.432(3) . ? C9 C1 1.415(3) . ? C19 C20 1.349(4) . ? C18 C17 1.373(4) . ? C20 C17 1.410(4) 2_765 ? C17 C20 1.410(4) 2_765 ? 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 C6 C5 122.1(2) . . ? C4 C3 C2 121.6(2) . . ? C14 C13 C11 121.06(18) . . ? C14 C13 C12 121.35(18) . . ? C11 C13 C12 117.58(18) . . ? C4 C10 C9 119.59(18) . . ? C4 C10 C5 121.20(18) . . ? C9 C10 C5 119.21(18) . . ? C19 C21 C18 121.8(2) . . ? C19 C21 C21 119.6(3) . 2_765 ? C18 C21 C21 118.6(3) . 2_765 ? C3 C4 C10 118.38(19) . . ? C3 C4 C5 122.27(19) . 2_675 ? C10 C4 C5 119.35(17) . 2_675 ? C6 C5 C10 118.23(19) . . ? C6 C5 C4 122.33(18) . 2_675 ? C10 C5 C4 119.44(17) . 2_675 ? N2 C16 C14 178.5(2) . . ? C7 C8 C9 120.6(2) . . ? C8 C7 C6 120.2(2) . . ? C1 C2 C3 120.7(2) . . ? C12 C11 C13 121.47(19) 2_775 . ? C11 C12 C13 120.94(19) 2_775 . ? N1 C15 C14 177.8(2) . . ? C8 C9 C1 120.7(2) . . ? C8 C9 C10 119.7(2) . . ? C1 C9 C10 119.6(2) . . ? C13 C14 C16 121.72(19) . . ? C13 C14 C15 120.91(19) . . ? C16 C14 C15 117.37(18) . . ? C2 C1 C9 120.1(2) . . ? C20 C19 C21 120.5(3) . . ? C17 C18 C21 120.0(2) . . ? C19 C20 C17 120.5(3) . 2_765 ? C18 C17 C20 120.8(3) . 2_765 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.209 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 957179' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyrene-perylene-7,7,8,8-tetracyanoquinodimethane complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12, C12 H4 N4, C16 H10' _chemical_formula_sum 'C48 H26 N4' _chemical_formula_weight 658.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2362(15) _cell_length_b 11.072(3) _cell_length_c 11.308(3) _cell_angle_alpha 62.06(2) _cell_angle_beta 86.353(19) _cell_angle_gamma 81.766(19) _cell_volume 792.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 342 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 10239 _diffrn_reflns_av_R_equivalents 0.0941 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.75 _reflns_number_total 2913 _reflns_number_gt 1953 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1812P)^2^+0.0000P] 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 2913 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.2735 _refine_ls_wR_factor_gt 0.2492 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 C4 C 0.4051(4) 0.1375(3) 0.4229(3) 0.0214(7) Uani 1 1 d . . . C3 C 0.3126(4) 0.2686(3) 0.3450(3) 0.0264(7) Uani 1 1 d . . . C6 C 0.4990(4) 0.1264(3) 0.2142(3) 0.0248(7) Uani 1 1 d . . . C8 C 0.4061(4) 0.0738(3) 0.5691(3) 0.0228(7) Uani 1 1 d . . . C10 C 0.3201(5) 0.0779(4) 0.7799(3) 0.0299(8) Uani 1 1 d . . . C5 C 0.4998(4) 0.0632(3) 0.3564(3) 0.0216(7) Uani 1 1 d . . . C9 C 0.3184(4) 0.1415(3) 0.6394(3) 0.0260(7) Uani 1 1 d . . . C2 C 0.3140(4) 0.3308(3) 0.2045(3) 0.0287(8) Uani 1 1 d . . . C1 C 0.4064(4) 0.2613(3) 0.1391(3) 0.0269(7) Uani 1 1 d . . . C7 C 0.5920(4) 0.0528(4) 0.1477(3) 0.0285(8) Uani 1 1 d . . . N1 N -0.1561(4) 0.3601(3) 0.0673(3) 0.0383(8) Uani 1 1 d . . . N2 N 0.1755(4) -0.0180(3) 0.1003(3) 0.0383(8) Uani 1 1 d . . . C13 C 0.0030(4) 0.0593(3) 0.3581(3) 0.0224(7) Uani 1 1 d . . . C14 C 0.0051(4) 0.1149(3) 0.2208(3) 0.0249(7) Uani 1 1 d . . . C12 C 0.0918(4) -0.0790(3) 0.4403(3) 0.0246(7) Uani 1 1 d . . . C11 C -0.0879(4) 0.1352(3) 0.4241(3) 0.0242(7) Uani 1 1 d . . . C15 C -0.0843(5) 0.2507(3) 0.1365(3) 0.0279(8) Uani 1 1 d . . . C16 C 0.0974(4) 0.0416(3) 0.1527(3) 0.0271(7) Uani 1 1 d . . . C20 C 0.0648(5) 0.5011(3) 0.5450(3) 0.0291(8) Uani 1 1 d . . . C19 C 0.0339(5) 0.4315(3) 0.6849(4) 0.0319(8) Uani 1 1 d . . . C21 C 0.2228(5) 0.5715(3) 0.4941(4) 0.0299(8) Uani 1 1 d . . . C18 C 0.1610(5) 0.4351(4) 0.7719(4) 0.0336(8) Uani 1 1 d . . . C23 C -0.1261(5) 0.3592(4) 0.7340(4) 0.0335(8) Uani 1 1 d . . . C24 C 0.2477(5) 0.6427(4) 0.3506(4) 0.0343(8) Uani 1 1 d . . . C22 C 0.3474(5) 0.5714(4) 0.5838(4) 0.0335(8) Uani 1 1 d . . . C17 C 0.3167(5) 0.5043(4) 0.7204(4) 0.0359(9) Uani 1 1 d . . . H12 H 0.152(6) -0.149(4) 0.409(4) 0.044(11) Uiso 1 1 d . . . H11 H -0.158(5) 0.237(3) 0.366(4) 0.020(8) Uiso 1 1 d . . . H24 H 0.356(5) 0.702(4) 0.303(4) 0.029(9) Uiso 1 1 d . . . H1 H 0.418(4) 0.302(3) 0.036(3) 0.017(7) Uiso 1 1 d . . . H10 H 0.255(5) 0.119(3) 0.841(4) 0.025(8) Uiso 1 1 d . . . H3 H 0.233(6) 0.332(4) 0.377(5) 0.051(12) Uiso 1 1 d . . . H2 H 0.243(5) 0.429(4) 0.154(4) 0.026(9) Uiso 1 1 d . . . H9 H 0.257(5) 0.245(4) 0.594(4) 0.030(9) Uiso 1 1 d . . . H7 H 0.587(5) 0.099(3) 0.050(4) 0.022(8) Uiso 1 1 d . . . H22 H 0.460(5) 0.622(4) 0.551(4) 0.030(9) Uiso 1 1 d . . . H23 H -0.133(6) 0.302(5) 0.832(5) 0.055(12) Uiso 1 1 d . . . H18 H 0.133(5) 0.391(4) 0.870(4) 0.039(10) Uiso 1 1 d . . . H17 H 0.416(7) 0.515(5) 0.782(5) 0.065(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C4 0.0149(14) 0.0269(16) 0.0214(16) -0.0107(14) 0.0024(12) -0.0027(12) C3 0.0168(15) 0.0307(17) 0.0283(17) -0.0121(15) 0.0000(12) 0.0013(13) C6 0.0171(15) 0.0330(17) 0.0222(16) -0.0111(14) 0.0010(12) -0.0036(13) C8 0.0162(15) 0.0284(16) 0.0219(16) -0.0111(14) 0.0014(12) -0.0002(12) C10 0.0258(17) 0.0386(19) 0.0267(18) -0.0169(15) 0.0053(14) -0.0042(14) C5 0.0132(14) 0.0258(16) 0.0243(17) -0.0112(14) 0.0014(12) 0.0001(12) C9 0.0175(15) 0.0315(17) 0.0276(17) -0.0140(15) 0.0005(13) 0.0020(13) C2 0.0214(16) 0.0262(16) 0.0296(18) -0.0074(14) -0.0063(13) 0.0058(13) C1 0.0209(16) 0.0327(17) 0.0206(16) -0.0074(14) 0.0006(13) -0.0024(13) C7 0.0196(16) 0.0415(19) 0.0245(17) -0.0161(16) 0.0017(13) -0.0023(14) N1 0.0341(17) 0.0396(17) 0.0292(17) -0.0077(14) -0.0038(13) 0.0027(13) N2 0.0353(17) 0.0490(19) 0.0310(16) -0.0203(15) 0.0041(13) -0.0019(14) C13 0.0183(15) 0.0254(16) 0.0204(16) -0.0078(14) 0.0012(12) -0.0045(12) C14 0.0184(15) 0.0298(17) 0.0227(16) -0.0093(14) 0.0004(12) -0.0024(12) C12 0.0173(15) 0.0282(17) 0.0254(17) -0.0114(14) 0.0006(12) 0.0023(12) C11 0.0166(15) 0.0267(16) 0.0258(17) -0.0102(14) -0.0009(13) 0.0008(12) C15 0.0244(16) 0.0369(19) 0.0190(16) -0.0097(15) -0.0001(13) -0.0051(14) C16 0.0201(16) 0.0353(18) 0.0215(16) -0.0100(15) -0.0009(13) -0.0015(13) C20 0.0285(18) 0.0246(16) 0.0325(18) -0.0143(14) -0.0014(14) 0.0055(13) C19 0.0298(18) 0.0246(16) 0.040(2) -0.0168(15) -0.0030(15) 0.0068(13) C21 0.0273(18) 0.0266(16) 0.0361(19) -0.0173(15) -0.0005(14) 0.0063(13) C18 0.0359(19) 0.0295(17) 0.0307(19) -0.0122(15) -0.0022(15) 0.0040(14) C23 0.0363(19) 0.0302(18) 0.0292(19) -0.0118(16) 0.0009(15) 0.0025(14) C24 0.0319(19) 0.0311(18) 0.039(2) -0.0176(16) 0.0037(16) 0.0010(15) C22 0.0271(18) 0.0325(18) 0.040(2) -0.0176(17) -0.0029(15) 0.0011(14) C17 0.0324(19) 0.0366(19) 0.039(2) -0.0193(17) -0.0055(16) 0.0054(15) _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 C4 C3 1.389(5) . ? C4 C5 1.437(4) . ? C4 C8 1.462(4) . ? C3 C2 1.405(5) . ? C6 C1 1.414(5) . ? C6 C5 1.422(4) . ? C6 C7 1.427(5) . ? C8 C9 1.398(4) . ? C8 C5 1.433(5) 2_656 ? C10 C7 1.364(5) 2_656 ? C10 C9 1.405(5) . ? C5 C8 1.433(5) 2_656 ? C2 C1 1.382(5) . ? C7 C10 1.364(5) 2_656 ? N1 C15 1.154(4) . ? N2 C16 1.150(4) . ? C13 C14 1.376(4) . ? C13 C11 1.436(4) . ? C13 C12 1.443(5) . ? C14 C15 1.430(5) . ? C14 C16 1.436(5) . ? C12 C11 1.358(5) 2_556 ? C11 C12 1.358(5) 2_556 ? C20 C21 1.413(5) . ? C20 C19 1.417(5) . ? C20 C20 1.437(7) 2_566 ? C19 C18 1.407(5) . ? C19 C23 1.434(5) . ? C21 C22 1.399(5) . ? C21 C24 1.446(5) . ? C18 C17 1.393(5) . ? C23 C24 1.350(5) 2_566 ? C24 C23 1.350(5) 2_566 ? C22 C17 1.385(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 C3 C4 C5 118.3(3) . . ? C3 C4 C8 121.9(3) . . ? C5 C4 C8 119.8(3) . . ? C4 C3 C2 121.9(3) . . ? C1 C6 C5 120.2(3) . . ? C1 C6 C7 120.2(3) . . ? C5 C6 C7 119.6(3) . . ? C9 C8 C5 118.6(3) . 2_656 ? C9 C8 C4 122.4(3) . . ? C5 C8 C4 119.0(3) 2_656 . ? C7 C10 C9 120.7(3) 2_656 . ? C6 C5 C8 119.4(3) . 2_656 ? C6 C5 C4 119.4(3) . . ? C8 C5 C4 121.2(3) 2_656 . ? C8 C9 C10 121.5(3) . . ? C1 C2 C3 120.4(3) . . ? C2 C1 C6 119.7(3) . . ? C10 C7 C6 120.2(3) 2_656 . ? C14 C13 C11 121.7(3) . . ? C14 C13 C12 120.4(3) . . ? C11 C13 C12 117.9(3) . . ? C13 C14 C15 121.8(3) . . ? C13 C14 C16 122.6(3) . . ? C15 C14 C16 115.6(3) . . ? C11 C12 C13 120.7(3) 2_556 . ? C12 C11 C13 121.4(3) 2_556 . ? N1 C15 C14 179.3(4) . . ? N2 C16 C14 178.1(3) . . ? C21 C20 C19 120.3(3) . . ? C21 C20 C20 120.1(4) . 2_566 ? C19 C20 C20 119.6(4) . 2_566 ? C18 C19 C20 119.1(3) . . ? C18 C19 C23 121.7(3) . . ? C20 C19 C23 119.2(3) . . ? C22 C21 C20 119.0(3) . . ? C22 C21 C24 122.6(3) . . ? C20 C21 C24 118.4(3) . . ? C17 C18 C19 120.0(3) . . ? C24 C23 C19 121.1(3) 2_566 . ? C23 C24 C21 121.5(3) 2_566 . ? C17 C22 C21 120.8(3) . . ? C22 C17 C18 120.8(3) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.429 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 957180' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pyrentq _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyrene-7,7,8,8-tetracyanoquinodimethane complex (2:1) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H4 N4, 2(C16 H10)' _chemical_formula_sum 'C44 H24 N4' _chemical_formula_weight 608.67 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 7.004(2) _cell_length_b 10.090(5) _cell_length_c 11.783(5) _cell_angle_alpha 107.42(5) _cell_angle_beta 106.46(3) _cell_angle_gamma 93.44(4) _cell_volume 752.4(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 10917 _diffrn_reflns_av_R_equivalents 0.2214 _diffrn_reflns_av_sigmaI/netI 0.1286 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2667 _reflns_number_gt 1454 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1590P)^2^+0.0000P] 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 2667 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1418 _refine_ls_R_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.2737 _refine_ls_wR_factor_gt 0.2292 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.002 _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 C1 C 0.0621(5) 0.6450(4) 0.0309(4) 0.0395(10) Uani 1 1 d . . . C2 C -0.0274(5) 0.5563(4) -0.0984(4) 0.0386(10) Uani 1 1 d . . . H2 H -0.053(6) 0.600(4) -0.167(4) 0.042(11) Uiso 1 1 d . . . C3 C 0.1229(5) 0.7864(4) 0.0573(4) 0.0393(10) Uani 1 1 d . . . N7 N 0.0658(5) 0.8966(4) -0.1174(4) 0.0491(10) Uani 1 1 d . . . C5 C 0.0875(5) 0.5839(4) 0.1264(4) 0.0401(10) Uani 1 1 d . . . H5 H 0.158(6) 0.659(4) 0.217(4) 0.047(11) Uiso 1 1 d . . . N8 N 0.2987(6) 0.9483(4) 0.2858(4) 0.0571(11) Uani 1 1 d . . . C4 C 0.0945(6) 0.8486(4) -0.0376(4) 0.0407(10) Uani 1 1 d . . . C6 C 0.2196(6) 0.8781(4) 0.1843(4) 0.0450(11) Uani 1 1 d . . . C9 C 0.5109(5) 0.5640(4) 0.9865(4) 0.0376(9) Uani 1 1 d . . . C10 C 0.4420(5) 0.5624(4) 0.8599(4) 0.0389(10) Uani 1 1 d . . . C11 C 0.5998(5) 0.6921(4) 1.0858(4) 0.0396(10) Uani 1 1 d . . . C12 C 0.4650(6) 0.6889(5) 0.8362(4) 0.0439(10) Uani 1 1 d . . . H12 H 0.404(6) 0.685(4) 0.739(4) 0.040(10) Uiso 1 1 d . . . C13 C 0.3542(6) 0.4310(4) 0.7624(4) 0.0425(10) Uani 1 1 d . . . H13 H 0.323(5) 0.435(4) 0.672(4) 0.032(9) Uiso 1 1 d . . . C14 C 0.6662(6) 0.6896(5) 1.2119(4) 0.0437(10) Uani 1 1 d . . . H14 H 0.723(7) 0.784(5) 1.279(4) 0.053(12) Uiso 1 1 d . . . C15 C 0.6206(6) 0.8163(4) 1.0565(4) 0.0456(11) Uani 1 1 d . . . H15 H 0.685(6) 0.909(4) 1.127(4) 0.041(10) Uiso 1 1 d . . . C16 C 0.5544(6) 0.8143(5) 0.9347(4) 0.0493(11) Uani 1 1 d . . . H16 H 0.557(7) 0.908(5) 0.908(4) 0.064(13) Uiso 1 1 d . . . C17 C 0.0430(6) 0.5690(4) 0.5063(3) 0.0396(10) Uani 1 1 d . . . C18 C 0.2074(6) 0.5845(4) 0.4605(3) 0.0430(10) Uani 1 1 d . . . C19 C 0.2788(6) 0.4626(5) 0.4016(4) 0.0472(11) Uani 1 1 d . . . H19 H 0.384(7) 0.475(5) 0.368(4) 0.062(14) Uiso 1 1 d . . . C20 C -0.0322(6) 0.6889(5) 0.5657(4) 0.0460(11) Uani 1 1 d . . . C21 C 0.1970(6) 0.3314(5) 0.3878(4) 0.0469(11) Uani 1 1 d . . . H21 H 0.246(6) 0.244(4) 0.340(4) 0.042(10) Uiso 1 1 d . . . C22 C 0.0551(7) 0.8212(5) 0.5775(4) 0.0496(11) Uani 1 1 d . . . H22 H -0.006(6) 0.901(5) 0.613(4) 0.052(12) Uiso 1 1 d . . . C23 C 0.2880(7) 0.7208(5) 0.4739(4) 0.0509(12) Uani 1 1 d . . . H23 H 0.407(6) 0.737(4) 0.437(3) 0.032(9) Uiso 1 1 d . . . C24 C 0.2142(7) 0.8379(5) 0.5318(4) 0.0552(12) Uani 1 1 d . . . H24 H 0.267(6) 0.933(5) 0.532(4) 0.046(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0219(19) 0.041(2) 0.048(2) 0.0098(19) 0.0062(17) 0.0024(16) C2 0.027(2) 0.039(2) 0.041(2) 0.0089(19) 0.0041(17) 0.0009(16) C3 0.0239(19) 0.042(2) 0.047(2) 0.0113(19) 0.0074(17) 0.0040(16) N7 0.042(2) 0.040(2) 0.054(2) 0.0084(18) 0.0085(17) -0.0016(16) C5 0.027(2) 0.039(2) 0.045(2) 0.0079(19) 0.0032(17) 0.0006(17) N8 0.057(2) 0.049(2) 0.051(2) 0.0077(19) 0.0058(19) 0.0015(19) C4 0.032(2) 0.035(2) 0.045(2) 0.0023(19) 0.0083(18) 0.0029(17) C6 0.034(2) 0.046(2) 0.049(3) 0.011(2) 0.0085(19) 0.0026(18) C9 0.0231(18) 0.036(2) 0.045(2) 0.0013(18) 0.0094(16) 0.0021(16) C10 0.0245(19) 0.043(2) 0.042(2) 0.0073(18) 0.0073(17) 0.0016(16) C11 0.026(2) 0.040(2) 0.046(2) 0.0072(18) 0.0096(17) -0.0012(16) C12 0.031(2) 0.055(3) 0.044(2) 0.016(2) 0.0099(18) 0.0089(19) C13 0.026(2) 0.052(3) 0.041(2) 0.009(2) 0.0057(17) 0.0016(18) C14 0.031(2) 0.045(3) 0.047(2) 0.006(2) 0.0103(18) 0.0014(18) C15 0.029(2) 0.039(2) 0.061(3) 0.009(2) 0.013(2) -0.0015(17) C16 0.034(2) 0.048(3) 0.064(3) 0.017(2) 0.016(2) 0.0040(19) C17 0.030(2) 0.048(2) 0.032(2) 0.0084(18) 0.0013(16) 0.0037(17) C18 0.029(2) 0.055(3) 0.031(2) 0.0060(19) 0.0011(17) -0.0023(18) C19 0.031(2) 0.062(3) 0.035(2) 0.002(2) 0.0056(18) 0.001(2) C20 0.036(2) 0.052(3) 0.038(2) 0.0049(19) 0.0031(18) 0.0043(19) C21 0.039(2) 0.054(3) 0.035(2) 0.002(2) 0.0046(19) 0.007(2) C22 0.047(3) 0.049(3) 0.040(2) 0.007(2) 0.003(2) 0.007(2) C23 0.037(2) 0.064(3) 0.041(2) 0.010(2) 0.0054(19) -0.004(2) C24 0.051(3) 0.056(3) 0.050(3) 0.015(2) 0.007(2) -0.004(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 C1 C3 1.379(5) . ? C1 C5 1.412(6) . ? C1 C2 1.445(6) . ? C2 C5 1.363(6) 2_565 ? C3 C4 1.411(6) . ? C3 C6 1.441(6) . ? N7 C4 1.157(5) . ? C5 C2 1.363(6) 2_565 ? N8 C6 1.144(5) . ? C9 C11 1.419(6) . ? C9 C10 1.427(6) . ? C9 C9 1.428(8) 2_667 ? C10 C12 1.396(6) . ? C10 C13 1.430(6) . ? C11 C15 1.406(6) . ? C11 C14 1.434(6) . ? C12 C16 1.397(6) . ? C13 C14 1.347(6) 2_667 ? C14 C13 1.347(6) 2_667 ? C15 C16 1.371(6) . ? C17 C20 1.418(6) . ? C17 C18 1.422(6) . ? C17 C17 1.430(8) 2_566 ? C18 C23 1.401(6) . ? C18 C19 1.415(6) . ? C19 C21 1.355(6) . ? C20 C22 1.385(6) . ? C20 C21 1.439(6) 2_566 ? C21 C20 1.439(6) 2_566 ? C22 C24 1.389(7) . ? C23 C24 1.385(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 C5 121.9(4) . . ? C3 C1 C2 119.1(4) . . ? C5 C1 C2 119.1(4) . . ? C5 C2 C1 119.9(4) 2_565 . ? C1 C3 C4 122.1(4) . . ? C1 C3 C6 121.2(4) . . ? C4 C3 C6 116.7(4) . . ? C2 C5 C1 121.0(4) 2_565 . ? N7 C4 C3 177.9(4) . . ? N8 C6 C3 178.3(5) . . ? C11 C9 C10 120.4(4) . . ? C11 C9 C9 119.8(5) . 2_667 ? C10 C9 C9 119.8(4) . 2_667 ? C12 C10 C9 118.6(4) . . ? C12 C10 C13 122.7(4) . . ? C9 C10 C13 118.6(4) . . ? C15 C11 C9 118.6(4) . . ? C15 C11 C14 122.7(4) . . ? C9 C11 C14 118.7(4) . . ? C10 C12 C16 120.6(4) . . ? C14 C13 C10 121.4(4) 2_667 . ? C13 C14 C11 121.6(4) 2_667 . ? C16 C15 C11 120.9(4) . . ? C15 C16 C12 121.0(4) . . ? C20 C17 C18 120.4(4) . . ? C20 C17 C17 120.5(5) . 2_566 ? C18 C17 C17 119.1(5) . 2_566 ? C23 C18 C19 123.2(4) . . ? C23 C18 C17 117.8(4) . . ? C19 C18 C17 119.0(4) . . ? C21 C19 C18 122.4(4) . . ? C22 C20 C17 119.2(4) . . ? C22 C20 C21 122.2(4) . 2_566 ? C17 C20 C21 118.6(4) . 2_566 ? C19 C21 C20 120.4(4) . 2_566 ? C20 C22 C24 121.1(5) . . ? C24 C23 C18 121.7(4) . . ? C23 C24 C22 119.8(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.353 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 957181' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Piren_TCNQ _audit_creation_method SHELXL-97 _chemical_name_systematic ; Pyrene-7,7,8,8-tetracyanoquinodimethane complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H4 N4, C16 H10' _chemical_formula_sum 'C28 H14 N4' _chemical_formula_weight 406.43 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 6.9917(14) _cell_length_b 10.069(2) _cell_length_c 14.671(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.52(3) _cell_angle_gamma 90.00 _cell_volume 1004.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5316 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.20 _exptl_crystal_description Prism _exptl_crystal_colour Purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator TRIUMPH _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9996 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1779 _reflns_number_gt 1527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2013.2-0 (Bruker AXS Inc., 2012)' _computing_cell_refinement 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_data_reduction 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^)+(0.0444P)^2^+0.1972P] 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 1779 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 C7 C 0.01728(16) 0.56799(12) 0.49113(8) 0.0210(3) Uani 1 1 d . . . C2 C -0.07769(17) 0.52228(14) 0.32207(9) 0.0264(3) Uani 1 1 d . . . C6 C 0.08331(16) 0.65698(13) 0.56736(8) 0.0230(3) Uani 1 1 d . . . C8 C -0.01367(17) 0.61472(13) 0.39736(8) 0.0235(3) Uani 1 1 d . . . C1 C -0.11024(17) 0.39383(14) 0.33876(9) 0.0254(3) Uani 1 1 d . . . C3 C 0.02363(18) 0.74854(14) 0.38191(9) 0.0279(3) Uani 1 1 d . . . C4 C 0.08775(18) 0.83416(14) 0.45664(9) 0.0291(3) Uani 1 1 d . . . C5 C 0.11685(18) 0.78958(14) 0.54825(9) 0.0273(3) Uani 1 1 d . . . C10 C 1.01871(16) 0.08828(12) 0.07594(8) 0.0192(3) Uani 1 1 d . . . C11 C 0.94165(15) 0.13340(12) -0.01927(7) 0.0182(3) Uani 1 1 d . . . C13 C 0.90044(17) 0.35799(12) 0.03738(8) 0.0203(3) Uani 1 1 d . . . C9 C 1.07363(16) -0.03850(12) 0.09401(8) 0.0192(3) Uani 1 1 d . . . C12 C 0.88384(16) 0.26323(12) -0.03670(7) 0.0191(3) Uani 1 1 d . . . C14 C 0.79891(17) 0.31082(12) -0.12947(8) 0.0217(3) Uani 1 1 d . . . N1 N 0.91356(16) 0.43425(11) 0.09686(7) 0.0274(3) Uani 1 1 d . . . N2 N 0.72725(16) 0.34874(11) -0.20359(7) 0.0307(3) Uani 1 1 d . . . H1 H -0.1531(19) 0.3320(14) 0.2872(10) 0.028(3) Uiso 1 1 d . . . H3 H 0.008(2) 0.7812(14) 0.3179(10) 0.031(4) Uiso 1 1 d . . . H4 H 0.114(2) 0.9281(15) 0.4443(9) 0.030(4) Uiso 1 1 d . . . H9 H 1.1242(18) -0.0659(12) 0.1582(9) 0.018(3) Uiso 1 1 d . . . H10 H 1.0295(18) 0.1516(13) 0.1273(9) 0.022(3) Uiso 1 1 d . . . H2 H -0.096(2) 0.5550(14) 0.2567(11) 0.036(4) Uiso 1 1 d . . . H5 H 0.1614(19) 0.8522(14) 0.6012(10) 0.031(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.0110(5) 0.0304(7) 0.0222(6) -0.0040(5) 0.0051(5) 0.0045(5) C2 0.0188(6) 0.0408(8) 0.0195(7) -0.0017(6) 0.0043(5) 0.0057(6) C6 0.0132(6) 0.0303(7) 0.0258(6) -0.0063(5) 0.0049(5) 0.0028(5) C8 0.0145(6) 0.0334(7) 0.0232(6) -0.0016(5) 0.0059(5) 0.0057(5) C1 0.0169(6) 0.0380(8) 0.0201(6) -0.0107(6) 0.0020(5) 0.0027(6) C3 0.0206(6) 0.0355(8) 0.0286(7) 0.0031(6) 0.0077(5) 0.0070(6) C4 0.0201(6) 0.0283(8) 0.0396(8) -0.0003(6) 0.0085(6) 0.0024(6) C5 0.0171(6) 0.0317(7) 0.0328(7) -0.0089(6) 0.0052(5) 0.0021(5) C10 0.0157(6) 0.0264(7) 0.0156(6) -0.0028(5) 0.0039(5) -0.0043(5) C11 0.0128(5) 0.0257(7) 0.0165(6) -0.0012(5) 0.0042(4) -0.0054(5) C13 0.0190(6) 0.0230(7) 0.0184(6) 0.0033(5) 0.0037(5) -0.0015(5) C9 0.0163(6) 0.0283(7) 0.0127(6) 0.0003(5) 0.0026(5) -0.0041(5) C12 0.0166(6) 0.0252(7) 0.0155(6) -0.0010(5) 0.0039(5) -0.0049(5) C14 0.0222(6) 0.0224(7) 0.0210(7) -0.0020(5) 0.0063(5) -0.0051(5) N1 0.0314(6) 0.0278(6) 0.0230(6) -0.0018(5) 0.0061(5) -0.0012(5) N2 0.0346(6) 0.0341(7) 0.0220(6) 0.0034(5) 0.0037(5) -0.0050(5) _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 C7 C8 1.4218(17) . ? C7 C6 1.4232(17) . ? C7 C7 1.425(3) 3_566 ? C2 C1 1.346(2) . ? C2 C8 1.4337(18) . ? C6 C5 1.3955(19) . ? C6 C1 1.4396(18) 3_566 ? C8 C3 1.4011(19) . ? C1 C6 1.4396(18) 3_566 ? C3 C4 1.384(2) . ? C4 C5 1.3861(19) . ? C10 C9 1.3417(18) . ? C10 C11 1.4477(16) . ? C11 C12 1.3747(17) . ? C11 C9 1.4394(16) 3_755 ? C13 N1 1.1498(16) . ? C13 C12 1.4305(17) . ? C9 C11 1.4394(16) 3_755 ? C12 C14 1.4340(17) . ? C14 N2 1.1509(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 C8 C7 C6 120.00(12) . . ? C8 C7 C7 120.06(14) . 3_566 ? C6 C7 C7 119.94(14) . 3_566 ? C1 C2 C8 121.29(12) . . ? C5 C6 C7 118.91(12) . . ? C5 C6 C1 122.81(12) . 3_566 ? C7 C6 C1 118.28(12) . 3_566 ? C3 C8 C7 118.87(12) . . ? C3 C8 C2 122.42(12) . . ? C7 C8 C2 118.69(12) . . ? C2 C1 C6 121.72(12) . 3_566 ? C4 C3 C8 120.59(12) . . ? C3 C4 C5 120.88(13) . . ? C4 C5 C6 120.75(12) . . ? C9 C10 C11 120.93(11) . . ? C12 C11 C9 121.56(10) . 3_755 ? C12 C11 C10 120.32(10) . . ? C9 C11 C10 118.12(11) 3_755 . ? N1 C13 C12 179.91(17) . . ? C10 C9 C11 120.95(11) . 3_755 ? C11 C12 C13 121.66(10) . . ? C11 C12 C14 122.20(10) . . ? C13 C12 C14 116.12(11) . . ? N2 C14 C12 178.70(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.257 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 957182' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_pctcnq _audit_creation_method SHELXL-97 _chemical_name_systematic ; Chrysene-7,7,8,8-tetracyanoquinodimethane complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12, C12 H4 N4' _chemical_formula_sum 'C30 H16 N4' _chemical_formula_weight 432.47 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 7.1533(5) _cell_length_b 7.9721(5) _cell_length_c 9.2258(5) _cell_angle_alpha 80.107(5) _cell_angle_beta 89.790(5) _cell_angle_gamma 86.670(5) _cell_volume 517.41(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Black _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 7076 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0140 _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 -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 25.20 _reflns_number_total 1860 _reflns_number_gt 1647 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0532P)^2^+0.0710P] 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 1860 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 C1 C 0.05380(13) 0.11703(12) 0.37516(11) 0.0142(2) Uani 1 1 d . . . C2 C 0.00595(13) -0.05385(12) 0.36107(11) 0.0149(2) Uani 1 1 d . . . C3 C 0.04477(13) 0.16468(13) 0.51982(11) 0.0152(2) Uani 1 1 d . . . C4 C 0.10658(13) 0.23130(12) 0.25421(11) 0.0152(2) Uani 1 1 d . . . C5 C 0.11891(13) 0.18986(12) 0.10860(11) 0.0162(2) Uani 1 1 d . . . C6 C 0.15126(13) 0.40232(13) 0.26556(10) 0.0163(2) Uani 1 1 d . . . C7 C 0.69306(14) 0.42024(14) 0.12340(12) 0.0206(3) Uani 1 1 d . . . C8 C 0.64150(14) 0.25961(14) 0.11219(12) 0.0201(3) Uani 1 1 d . . . C9 C 0.58555(13) 0.14635(13) 0.23928(11) 0.0172(2) Uani 1 1 d . . . C10 C 0.58544(13) 0.19936(13) 0.37881(11) 0.0161(2) Uani 1 1 d . . . C11 C 0.64183(14) 0.36514(13) 0.38604(12) 0.0184(2) Uani 1 1 d . . . C12 C 0.69314(14) 0.47295(13) 0.26100(12) 0.0198(3) Uani 1 1 d . . . C13 C 0.52881(13) -0.01993(13) 0.22891(11) 0.0186(2) Uani 1 1 d . . . C14 C 0.52818(13) 0.08157(12) 0.50778(11) 0.0156(2) Uani 1 1 d . . . C15 C 0.52721(13) 0.12875(13) 0.65051(11) 0.0169(2) Uani 1 1 d . . . H2 H 0.0102(16) -0.0853(15) 0.2630(14) 0.021(3) Uiso 1 1 d . . . H3 H 0.0769(16) 0.2833(15) 0.5313(13) 0.022(3) Uiso 1 1 d . . . H7 H 0.7303(17) 0.4973(16) 0.0328(15) 0.033(3) Uiso 1 1 d . . . H8 H 0.6440(18) 0.2214(16) 0.0154(15) 0.029(3) Uiso 1 1 d . . . H11 H 0.6446(17) 0.4011(15) 0.4855(14) 0.028(3) Uiso 1 1 d . . . H12 H 0.7322(17) 0.5896(17) 0.2692(14) 0.031(3) Uiso 1 1 d . . . H13 H 0.5311(17) -0.0548(15) 0.1292(14) 0.026(3) Uiso 1 1 d . . . H15 H 0.5673(16) 0.2426(16) 0.6626(13) 0.025(3) Uiso 1 1 d . . . N1 N 0.13093(12) 0.16216(11) -0.00952(10) 0.0235(2) Uani 1 1 d . . . N2 N 0.18562(12) 0.53976(11) 0.27332(10) 0.0238(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0094(5) 0.0172(5) 0.0154(5) -0.0020(4) -0.0013(4) 0.0016(4) C2 0.0131(5) 0.0172(5) 0.0147(5) -0.0044(4) -0.0011(4) 0.0009(4) C3 0.0134(5) 0.0157(5) 0.0165(5) -0.0032(4) -0.0016(4) -0.0001(4) C4 0.0131(5) 0.0166(5) 0.0160(5) -0.0031(4) -0.0010(4) 0.0003(4) C5 0.0156(5) 0.0151(5) 0.0168(6) 0.0005(4) 0.0010(4) -0.0026(4) C6 0.0154(5) 0.0209(6) 0.0119(5) -0.0010(4) 0.0000(4) -0.0007(4) C7 0.0173(5) 0.0215(6) 0.0205(6) 0.0036(4) -0.0005(4) -0.0012(4) C8 0.0176(5) 0.0249(6) 0.0171(6) -0.0013(4) -0.0022(4) -0.0008(4) C9 0.0107(5) 0.0191(5) 0.0210(6) -0.0021(4) -0.0025(4) 0.0012(4) C10 0.0094(5) 0.0205(5) 0.0174(5) -0.0015(4) -0.0010(4) 0.0029(4) C11 0.0136(5) 0.0201(5) 0.0214(6) -0.0041(4) -0.0002(4) 0.0024(4) C12 0.0159(5) 0.0177(5) 0.0248(6) -0.0015(4) -0.0004(4) 0.0011(4) C13 0.0157(5) 0.0223(5) 0.0184(6) -0.0063(4) -0.0012(4) 0.0005(4) C14 0.0098(5) 0.0180(5) 0.0187(6) -0.0034(4) -0.0016(4) 0.0029(4) C15 0.0133(5) 0.0181(5) 0.0203(5) -0.0065(4) -0.0004(4) -0.0003(4) N1 0.0272(5) 0.0241(5) 0.0196(5) -0.0045(4) 0.0028(4) -0.0048(4) N2 0.0273(5) 0.0215(5) 0.0229(5) -0.0033(4) -0.0004(4) -0.0053(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 C1 C4 1.3803(15) . ? C1 C3 1.4493(15) . ? C1 C2 1.4509(14) . ? C2 C3 1.3492(15) 2_556 ? C3 C2 1.3492(15) 2_556 ? C4 C5 1.4386(14) . ? C4 C6 1.4394(14) . ? C5 N1 1.1505(14) . ? C6 N2 1.1509(13) . ? C7 C8 1.3738(16) . ? C7 C12 1.4041(16) . ? C8 C9 1.4230(15) . ? C9 C10 1.4222(15) . ? C9 C13 1.4274(14) . ? C10 C11 1.4164(15) . ? C10 C14 1.4569(15) . ? C11 C12 1.3773(15) . ? C13 C15 1.3625(15) 2_656 ? C14 C14 1.414(2) 2_656 ? C14 C15 1.4301(15) . ? C15 C13 1.3625(15) 2_656 ? 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 120.81(9) . . ? C4 C1 C2 120.99(9) . . ? C3 C1 C2 118.20(9) . . ? C3 C2 C1 120.46(10) 2_556 . ? C2 C3 C1 121.33(10) 2_556 . ? C1 C4 C5 122.94(9) . . ? C1 C4 C6 121.79(9) . . ? C5 C4 C6 115.28(9) . . ? N1 C5 C4 177.67(10) . . ? N2 C6 C4 179.22(11) . . ? C8 C7 C12 120.09(10) . . ? C7 C8 C9 120.37(10) . . ? C10 C9 C8 119.67(10) . . ? C10 C9 C13 119.35(10) . . ? C8 C9 C13 120.98(10) . . ? C11 C10 C9 118.23(10) . . ? C11 C10 C14 122.85(10) . . ? C9 C10 C14 118.92(10) . . ? C12 C11 C10 120.89(10) . . ? C11 C12 C7 120.73(10) . . ? C15 C13 C9 121.53(10) 2_656 . ? C14 C14 C15 119.28(12) 2_656 . ? C14 C14 C10 119.81(12) 2_656 . ? C15 C14 C10 120.91(9) . . ? C13 C15 C14 121.11(10) 2_656 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.161 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 957183' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_new _audit_creation_method SHELXL-97 _chemical_name_systematic ; Phenanthrene-7,7,8,8-tetracyanoquinodimethane complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H4 N4, C14 H10' _chemical_formula_sum 'C26 H14 N4' _chemical_formula_weight 382.41 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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 '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 6.7083(9) _cell_length_b 8.0897(12) _cell_length_c 9.118(2) _cell_angle_alpha 101.212(16) _cell_angle_beta 97.720(15) _cell_angle_gamma 99.521(12) _cell_volume 471.55(14) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 198 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _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 4006 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0973 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4006 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1137P)^2^+0.0000P] 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 4006 _refine_ls_number_parameters 165 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.1716 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.2282 _refine_ls_wR_factor_gt 0.1763 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.969 _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 C1 C 0.9030(13) -0.1312(14) 0.6329(10) 0.0195(16) Uani 0.50 1 d PDU A -1 H1 H 0.8918 -0.1012 0.5368 0.023 Uiso 0.50 1 calc PR A -1 C2 C 0.8673(12) -0.3015(19) 0.6405(16) 0.020(3) Uani 0.50 1 d PD A -1 H2 H 0.8308 -0.3878 0.5492 0.024 Uiso 0.50 1 calc PR A -1 C3 C 0.8835(12) -0.3490(17) 0.779(2) 0.023(3) Uani 0.50 1 d PD A -1 H3 H 0.8581 -0.4672 0.7818 0.027 Uiso 0.50 1 calc PR A -1 C4 C 0.9383(14) -0.2210(11) 0.9157(10) 0.0165(16) Uani 0.50 1 d PDU A -1 C5 C 0.9750(15) -0.0465(14) 0.9070(12) 0.014(2) Uani 0.50 1 d PD A -1 C6 C 0.9550(16) -0.0040(14) 0.7639(12) 0.016(2) Uani 0.50 1 d PD A -1 H6 H 0.9776 0.1133 0.7576 0.019 Uiso 0.50 1 calc PR A -1 C7 C 0.9538(8) -0.2693(8) 1.0598(7) 0.0224(15) Uani 0.50 1 d PD A -1 H7 H 0.9277 -0.3876 1.0629 0.027 Uiso 0.50 1 calc PR A -1 C8 C 1.0041(8) -0.1510(7) 1.1883(7) 0.0203(15) Uani 0.50 1 d PD A -1 H8 H 1.0124 -0.1864 1.2820 0.024 Uiso 0.50 1 calc PR A -1 C9 C 1.0469(16) 0.0317(13) 1.1899(12) 0.016(2) Uani 0.50 1 d PD A -1 C10 C 1.0313(16) 0.0846(13) 1.0515(13) 0.014(2) Uani 0.50 1 d PD A -1 C11 C 1.1024(13) 0.1582(14) 1.3288(10) 0.0195(16) Uani 0.50 1 d PDU A -1 H11 H 1.1153 0.1235 1.4228 0.023 Uiso 0.50 1 calc PR A -1 C12 C 1.1373(13) 0.331(2) 1.3272(16) 0.020(3) Uani 0.50 1 d PD A -1 H12 H 1.1720 0.4139 1.4204 0.024 Uiso 0.50 1 calc PR A -1 C13 C 1.1226(14) 0.3834(17) 1.193(2) 0.023(3) Uani 0.50 1 d PD A -1 H13 H 1.1468 0.5027 1.1934 0.027 Uiso 0.50 1 calc PR A -1 C14 C 1.0724(14) 0.2631(11) 1.0550(11) 0.0165(16) Uani 0.50 1 d PDU A -1 H14 H 1.0655 0.3011 0.9625 0.020 Uiso 0.50 1 calc PR A -1 N2X N 0.3457(5) 0.4186(4) 0.7473(3) 0.0421(9) Uani 1 1 d . . . N4X N 0.3475(4) 0.7960(3) 0.4649(3) 0.0303(8) Uani 1 1 d . . . C3X C 0.4711(4) 0.8277(4) 1.0147(3) 0.0165(7) Uani 1 1 d . . . H3X H 0.4517 0.7108 1.0222 0.020 Uiso 1 1 calc R . . C5X C 0.4482(4) 0.8683(4) 0.8664(3) 0.0148(7) Uani 1 1 d . . . C7X C 0.4806(4) 1.0473(4) 0.8578(3) 0.0156(7) Uani 1 1 d . . . H7X H 0.4678 1.0767 0.7616 0.019 Uiso 1 1 calc R . . C8X C 0.3985(4) 0.7399(4) 0.7366(3) 0.0177(7) Uani 1 1 d . . . C9X C 0.3717(4) 0.7724(4) 0.5851(4) 0.0201(8) Uani 1 1 d . . . C10X C 0.3684(5) 0.5606(5) 0.7425(3) 0.0249(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0135(17) 0.028(3) 0.019(3) 0.011(2) 0.004(2) 0.0028(17) C2 0.0214(19) 0.024(5) 0.016(5) 0.005(4) 0.001(2) 0.007(2) C3 0.0162(19) 0.008(4) 0.043(6) 0.004(4) 0.000(2) 0.006(2) C4 0.0159(18) 0.017(3) 0.022(3) 0.012(2) 0.0036(19) 0.009(2) C5 0.0068(19) 0.016(5) 0.020(6) 0.003(3) 0.003(3) 0.004(3) C6 0.0119(19) 0.020(4) 0.020(6) 0.013(3) 0.004(3) 0.004(2) C7 0.014(3) 0.025(4) 0.034(4) 0.016(4) 0.010(3) 0.005(3) C8 0.014(3) 0.025(4) 0.028(4) 0.021(3) 0.007(3) 0.003(3) C9 0.0119(19) 0.020(4) 0.020(6) 0.013(3) 0.004(3) 0.004(2) C10 0.0068(19) 0.016(5) 0.020(6) 0.003(3) 0.003(3) 0.004(3) C11 0.0135(17) 0.028(3) 0.019(3) 0.011(2) 0.004(2) 0.0028(17) C12 0.0214(19) 0.024(5) 0.016(5) 0.005(4) 0.001(2) 0.007(2) C13 0.0162(19) 0.008(4) 0.043(6) 0.004(4) 0.000(2) 0.006(2) C14 0.0159(18) 0.017(3) 0.022(3) 0.012(2) 0.0036(19) 0.009(2) N2X 0.066(2) 0.0289(18) 0.0293(18) 0.0013(15) -0.0027(15) 0.0180(15) N4X 0.0375(17) 0.0335(17) 0.0205(16) 0.0033(14) 0.0042(13) 0.0121(13) C3X 0.0148(16) 0.0196(18) 0.0190(18) 0.0074(15) 0.0053(13) 0.0086(13) C5X 0.0079(14) 0.0190(17) 0.0178(18) 0.0023(13) 0.0009(13) 0.0071(12) C7X 0.0107(15) 0.0242(19) 0.0143(17) 0.0062(14) 0.0044(13) 0.0059(13) C8X 0.0142(15) 0.0191(17) 0.0188(18) 0.0025(14) -0.0009(14) 0.0057(13) C9X 0.0210(17) 0.0176(18) 0.0205(19) 0.0001(15) 0.0019(14) 0.0068(13) C10X 0.0271(18) 0.028(2) 0.0188(19) 0.0020(16) -0.0028(14) 0.0133(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.375(16) . ? C1 C6 1.378(14) . ? C2 C3 1.383(16) . ? C3 C4 1.421(16) . ? C4 C5 1.411(11) . ? C4 C7 1.438(9) . ? C5 C6 1.408(11) . ? C5 C10 1.481(6) . ? C7 C8 1.324(8) . ? C8 C9 1.455(10) . ? C9 C10 1.406(11) . ? C9 C11 1.425(13) . ? C10 C14 1.418(11) . ? C11 C12 1.380(15) . ? C12 C13 1.372(16) . ? C13 C14 1.392(16) . ? N2X C10X 1.144(4) . ? N4X C9X 1.144(4) . ? C3X C7X 1.347(4) 2_677 ? C3X C5X 1.446(4) . ? C5X C8X 1.375(3) . ? C5X C7X 1.447(4) . ? C7X C3X 1.347(4) 2_677 ? C8X C10X 1.443(4) . ? C8X C9X 1.450(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 C2 C1 C6 120.3(9) . . ? C1 C2 C3 121.1(11) . . ? C2 C3 C4 119.9(10) . . ? C5 C4 C3 118.6(8) . . ? C5 C4 C7 121.1(8) . . ? C3 C4 C7 120.3(9) . . ? C6 C5 C4 119.5(9) . . ? C6 C5 C10 122.9(8) . . ? C4 C5 C10 117.6(7) . . ? C1 C6 C5 120.5(9) . . ? C8 C7 C4 120.8(6) . . ? C7 C8 C9 121.8(6) . . ? C10 C9 C11 119.3(9) . . ? C10 C9 C8 119.2(8) . . ? C11 C9 C8 121.4(8) . . ? C9 C10 C14 118.5(9) . . ? C9 C10 C5 119.5(7) . . ? C14 C10 C5 122.0(7) . . ? C12 C11 C9 120.3(9) . . ? C13 C12 C11 120.8(11) . . ? C12 C13 C14 120.4(11) . . ? C13 C14 C10 120.7(9) . . ? C7X C3X C5X 121.1(3) 2_677 . ? C8X C5X C3X 120.8(3) . . ? C8X C5X C7X 120.8(3) . . ? C3X C5X C7X 118.4(2) . . ? C3X C7X C5X 120.4(3) 2_677 . ? C5X C8X C10X 121.7(3) . . ? C5X C8X C9X 123.4(3) . . ? C10X C8X C9X 114.9(3) . . ? N4X C9X C8X 178.8(3) . . ? N2X C10X C8X 179.6(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.555 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.124 _database_code_depnum_ccdc_archive 'CCDC 957184' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_naph_tcnq _audit_creation_method SHELXL-97 _chemical_name_systematic ; Naphthalene-TCNQ complex ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H4 N4, C10 H8' _chemical_formula_sum 'C22 H12 N4' _chemical_formula_weight 332.36 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 7.4928(10) _cell_length_b 7.8003(10) _cell_length_c 8.1026(11) _cell_angle_alpha 84.297(6) _cell_angle_beta 81.124(6) _cell_angle_gamma 61.343(5) _cell_volume 410.40(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 789 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 30.44 _exptl_crystal_description Block _exptl_crystal_colour Dark-purple _exptl_crystal_size_max 0.267 _exptl_crystal_size_mid 0.152 _exptl_crystal_size_min 0.084 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 172 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9749 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'SADABS V2012/1 (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator TRIUMPH _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8231 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0137 _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 -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 25.24 _reflns_number_total 1487 _reflns_number_gt 1302 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2013.2-0 (Bruker AXS Inc., 2012)' _computing_cell_refinement 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_data_reduction 'SAINT V8.27B (Bruker AXS Inc., 2012)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^)+(0.0500P)^2^+0.0743P] 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 1487 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C8 C 0.05654(15) 0.08113(15) 0.35030(13) 0.0176(2) Uani 1 1 d . . . C7 C -0.01150(16) 0.18507(15) 0.50429(13) 0.0183(3) Uani 1 1 d . . . C11 C 0.10944(16) 0.34532(16) 0.19645(13) 0.0197(3) Uani 1 1 d . . . C6 C 0.06408(16) -0.10772(15) 0.35306(13) 0.0185(3) Uani 1 1 d . . . C3 C 0.50560(16) 0.44345(15) 0.43383(14) 0.0200(3) Uani 1 1 d . . . N2 N 0.10693(15) 0.49410(14) 0.18668(12) 0.0258(3) Uani 1 1 d . . . C4 C 0.46378(17) 0.28425(16) 0.47315(15) 0.0238(3) Uani 1 1 d . . . C2 C 0.55780(17) 0.49370(17) 0.26723(14) 0.0234(3) Uani 1 1 d . . . C10 C 0.19460(17) 0.05241(15) 0.05335(13) 0.0213(3) Uani 1 1 d . . . C9 C 0.11568(16) 0.15778(15) 0.20530(13) 0.0187(3) Uani 1 1 d . . . N1 N 0.26215(16) -0.03318(14) -0.06805(12) 0.0293(3) Uani 1 1 d . . . C5 C 0.41305(17) 0.24014(17) 0.63446(16) 0.0270(3) Uani 1 1 d . . . C1 C 0.59717(17) 0.64808(17) 0.23428(15) 0.0265(3) Uani 1 1 d . . . H5 H 0.1097(19) -0.1772(18) 0.2520(16) 0.021(3) Uiso 1 1 d . . . H6 H -0.0188(18) 0.3139(18) 0.5032(15) 0.019(3) Uiso 1 1 d . . . H2 H 0.5626(19) 0.4172(19) 0.1790(16) 0.026(3) Uiso 1 1 d . . . H4 H 0.380(2) 0.133(2) 0.6626(16) 0.029(3) Uiso 1 1 d . . . H3 H 0.471(2) 0.2080(19) 0.3813(16) 0.029(3) Uiso 1 1 d . . . H1 H 0.635(2) 0.6793(19) 0.1165(18) 0.034(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C8 0.0143(5) 0.0179(5) 0.0205(5) -0.0009(4) -0.0049(4) -0.0066(4) C7 0.0173(5) 0.0161(6) 0.0222(6) -0.0024(4) -0.0036(4) -0.0078(4) C11 0.0200(6) 0.0227(6) 0.0167(5) -0.0014(4) -0.0016(4) -0.0104(5) C6 0.0172(5) 0.0182(6) 0.0198(6) -0.0040(4) -0.0028(4) -0.0073(4) C3 0.0140(5) 0.0175(6) 0.0255(6) -0.0022(4) -0.0031(4) -0.0045(4) N2 0.0308(6) 0.0244(6) 0.0260(5) -0.0014(4) -0.0026(4) -0.0161(4) C4 0.0200(6) 0.0192(6) 0.0322(6) -0.0034(5) -0.0062(5) -0.0079(5) C2 0.0195(6) 0.0229(6) 0.0237(6) -0.0041(5) -0.0023(5) -0.0062(5) C10 0.0261(6) 0.0192(6) 0.0208(6) 0.0031(5) -0.0034(5) -0.0129(5) C9 0.0187(5) 0.0177(5) 0.0206(6) -0.0019(4) -0.0033(4) -0.0090(4) N1 0.0421(6) 0.0249(5) 0.0215(5) -0.0019(4) 0.0006(4) -0.0175(5) C5 0.0215(6) 0.0211(6) 0.0392(7) 0.0034(5) -0.0046(5) -0.0111(5) C1 0.0205(6) 0.0272(6) 0.0265(6) 0.0034(5) -0.0001(5) -0.0085(5) _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 C8 C9 1.3741(15) . ? C8 C7 1.4430(15) . ? C8 C6 1.4449(15) . ? C7 C6 1.3431(16) 2_556 ? C7 H6 0.979(12) . ? C11 N2 1.1466(14) . ? C11 C9 1.4359(15) . ? C6 C7 1.3431(16) 2_556 ? C6 H5 0.952(13) . ? C3 C4 1.4162(16) . ? C3 C2 1.4169(16) . ? C3 C3 1.423(2) 2_666 ? C4 C5 1.3616(17) . ? C4 H3 0.976(13) . ? C2 C1 1.3642(17) . ? C2 H2 0.962(13) . ? C10 N1 1.1499(15) . ? C10 C9 1.4322(15) . ? C5 C1 1.4115(17) 2_666 ? C5 H4 0.977(14) . ? C1 C5 1.4115(17) 2_666 ? C1 H1 0.993(14) . ? 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 C9 C8 C7 121.09(10) . . ? C9 C8 C6 120.72(10) . . ? C7 C8 C6 118.19(10) . . ? C6 C7 C8 121.05(10) 2_556 . ? C6 C7 H6 120.2(7) 2_556 . ? C8 C7 H6 118.7(7) . . ? N2 C11 C9 178.72(11) . . ? C7 C6 C8 120.76(10) 2_556 . ? C7 C6 H5 120.8(8) 2_556 . ? C8 C6 H5 118.5(8) . . ? C4 C3 C2 122.14(10) . . ? C4 C3 C3 118.80(13) . 2_666 ? C2 C3 C3 119.06(13) . 2_666 ? C5 C4 C3 120.78(11) . . ? C5 C4 H3 121.1(8) . . ? C3 C4 H3 118.1(8) . . ? C1 C2 C3 120.45(11) . . ? C1 C2 H2 121.4(8) . . ? C3 C2 H2 118.1(8) . . ? N1 C10 C9 178.53(12) . . ? C8 C9 C10 122.02(10) . . ? C8 C9 C11 122.64(9) . . ? C10 C9 C11 115.31(9) . . ? C4 C5 C1 120.38(11) . 2_666 ? C4 C5 H4 121.4(8) . . ? C1 C5 H4 118.2(8) 2_666 . ? C2 C1 C5 120.53(11) . 2_666 ? C2 C1 H1 118.8(8) . . ? C5 C1 H1 120.7(8) 2_666 . ? 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 C9 C8 C7 C6 -178.21(10) . . . 2_556 ? C6 C8 C7 C6 0.81(16) . . . 2_556 ? C9 C8 C6 C7 178.21(9) . . . 2_556 ? C7 C8 C6 C7 -0.81(16) . . . 2_556 ? C2 C3 C4 C5 -179.68(10) . . . . ? C3 C3 C4 C5 0.21(19) 2_666 . . . ? C4 C3 C2 C1 -179.97(10) . . . . ? C3 C3 C2 C1 0.14(18) 2_666 . . . ? C7 C8 C9 C10 176.41(9) . . . . ? C6 C8 C9 C10 -2.58(16) . . . . ? C7 C8 C9 C11 -1.44(16) . . . . ? C6 C8 C9 C11 179.57(9) . . . . ? N1 C10 C9 C8 -102(4) . . . . ? N1 C10 C9 C11 76(4) . . . . ? N2 C11 C9 C8 162(5) . . . . ? N2 C11 C9 C10 -16(5) . . . . ? C3 C4 C5 C1 -0.49(17) . . . 2_666 ? C3 C2 C1 C5 0.13(17) . . . 2_666 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.207 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.033 _database_code_depnum_ccdc_archive 'CCDC 957185'