 
data_bper-TCNQ-100K
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             (benzo[ghi]perylene)TCNQ
_chemical_formula_moiety          '(C22 H12), (C12 H4 N4)'
_chemical_formula_sum 
 'C34 H16 N4' 
_chemical_formula_weight          480.53
 
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           'Orthorhombic'
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 '-x+1/2, -y, z+1/2' 
 
_cell_length_a                    7.1719(4) 
_cell_length_b                    10.8284(5) 
_cell_length_c                    29.7864(15) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2313.2(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used    8144
_cell_measurement_theta_min        2.74
_cell_measurement_theta_max       27.89
 
_exptl_crystal_description        'rod'
_exptl_crystal_colour             'black'
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.09 
_exptl_crystal_size_min           0.06 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.380 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              992 
_exptl_absorpt_coefficient_mu     0.083 
_exptl_absorpt_correction_type    numerical
_exptl_absorpt_correction_T_min   0.9629 
_exptl_absorpt_correction_T_max   0.9950 
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean  8.333
_diffrn_reflns_number             24522 
_diffrn_reflns_av_R_equivalents   0.0412 
_diffrn_reflns_av_sigmaI/netI     0.0327 
_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        -37 
_diffrn_reflns_limit_l_max        37 
_diffrn_reflns_theta_min          2.00 
_diffrn_reflns_theta_max          26.37 
_reflns_number_total              4716 
_reflns_number_gt                 3926 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection      'Bruker APEX2'
_computing_cell_refinement      'Bruker SAINT'
_computing_data_reduction       'Bruker SAINT'
_computing_structure_solution   'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics   'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0370P)²+0.4149P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0(3) 
_refine_ls_number_reflns          4716 
_refine_ls_number_parameters      343 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0522 
_refine_ls_R_factor_gt            0.0386 
_refine_ls_wR_factor_ref          0.0799 
_refine_ls_wR_factor_gt           0.0760 
_refine_ls_goodness_of_fit_ref    1.030 
_refine_ls_restrained_S_all       1.030 
_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 
C1 C -0.1240(2) 0.71081(17) 0.78529(6) 0.0199(4) Uani 1 1 d . . . 
H1 H -0.1709 0.6457 0.7684 0.024 Uiso 1 1 calc R . . 
C2 C -0.1210(2) 0.82856(18) 0.76694(6) 0.0234(4) Uani 1 1 d . . . 
H2 H -0.1647 0.8413 0.7379 0.028 Uiso 1 1 calc R . . 
C3 C -0.0535(3) 0.92694(17) 0.79150(6) 0.0237(4) Uani 1 1 d . . . 
H3 H -0.0527 1.0055 0.7789 0.028 Uiso 1 1 calc R . . 
C4 C 0.0136(2) 0.90996(16) 0.83510(6) 0.0194(4) Uani 1 1 d . . . 
C5 C 0.0843(2) 1.00972(17) 0.86127(6) 0.0228(4) Uani 1 1 d . . . 
H5 H 0.0865 1.0886 0.8489 0.027 Uiso 1 1 calc R . . 
C6 C 0.1483(2) 0.99298(17) 0.90356(6) 0.0226(4) Uani 1 1 d . . . 
H6 H 0.1924 1.0603 0.9198 0.027 Uiso 1 1 calc R . . 
C7 C 0.1487(2) 0.87326(17) 0.92351(6) 0.0191(4) Uani 1 1 d . . . 
C8 C 0.2237(2) 0.85192(18) 0.96673(6) 0.0232(4) Uani 1 1 d . . . 
H8 H 0.2718 0.9180 0.9830 0.028 Uiso 1 1 calc R . . 
C9 C 0.2271(3) 0.73651(18) 0.98511(6) 0.0229(4) Uani 1 1 d . . . 
H9 H 0.2802 0.7251 1.0133 0.028 Uiso 1 1 calc R . . 
C10 C 0.1509(2) 0.63364(17) 0.96202(5) 0.0199(4) Uani 1 1 d . . . 
C11 C 0.1458(3) 0.51320(18) 0.98125(6) 0.0243(4) Uani 1 1 d . . . 
H11 H 0.1937 0.5009 1.0099 0.029 Uiso 1 1 calc R . . 
C12 C 0.0730(3) 0.41679(18) 0.95865(6) 0.0245(4) Uani 1 1 d . . . 
H12 H 0.0686 0.3397 0.9724 0.029 Uiso 1 1 calc R . . 
C13 C 0.0020(2) 0.43015(16) 0.91389(6) 0.0210(4) Uani 1 1 d . . . 
C14 C -0.0693(2) 0.33038(16) 0.88968(7) 0.0248(4) Uani 1 1 d . . . 
H14 H -0.0758 0.2529 0.9030 0.030 Uiso 1 1 calc R . . 
C15 C -0.1298(2) 0.34564(17) 0.84637(6) 0.0233(4) Uani 1 1 d . . . 
H15 H -0.1738 0.2778 0.8304 0.028 Uiso 1 1 calc R . . 
C16 C -0.1264(2) 0.46089(16) 0.82589(6) 0.0210(4) Uani 1 1 d . . . 
H16 H -0.1685 0.4691 0.7965 0.025 Uiso 1 1 calc R . . 
C17 C -0.0606(2) 0.56459(15) 0.84890(6) 0.0168(4) Uani 1 1 d . . . 
C18 C -0.0582(2) 0.68785(16) 0.82874(6) 0.0172(4) Uani 1 1 d . . . 
C19 C 0.0106(2) 0.78896(15) 0.85416(5) 0.0158(4) Uani 1 1 d . . . 
C20 C 0.0790(2) 0.77177(16) 0.89889(6) 0.0162(4) Uani 1 1 d . . . 
C21 C 0.0781(2) 0.65134(16) 0.91832(5) 0.0166(4) Uani 1 1 d . . . 
C22 C 0.0058(2) 0.54916(15) 0.89346(5) 0.0160(4) Uani 1 1 d . . . 
C23 C 0.5166(2) 0.79093(16) 0.85578(5) 0.0155(4) Uani 1 1 d . . . 
C24 C 0.5700(2) 0.75316(15) 0.90021(5) 0.0163(4) Uani 1 1 d . . . 
H24 H 0.6137 0.8120 0.9204 0.020 Uiso 1 1 calc R . . 
C25 C 0.5583(2) 0.63486(15) 0.91324(5) 0.0159(4) Uani 1 1 d . . . 
H25 H 0.5938 0.6133 0.9422 0.019 Uiso 1 1 calc R . . 
C26 C 0.4917(2) 0.54062(15) 0.88310(5) 0.0163(4) Uani 1 1 d . . . 
C27 C 0.4390(2) 0.57834(16) 0.83837(5) 0.0171(4) Uani 1 1 d . . . 
H27 H 0.3958 0.5194 0.8182 0.020 Uiso 1 1 calc R . . 
C28 C 0.4510(2) 0.69654(15) 0.82536(5) 0.0169(4) Uani 1 1 d . . . 
H28 H 0.4166 0.7181 0.7963 0.020 Uiso 1 1 calc R . . 
C29 C 0.5284(2) 0.91332(16) 0.84333(5) 0.0171(4) Uani 1 1 d . . . 
C30 C 0.4750(2) 0.95545(16) 0.79941(6) 0.0196(4) Uani 1 1 d . . . 
C31 C 0.5951(2) 1.00480(16) 0.87414(6) 0.0185(4) Uani 1 1 d . . . 
C32 C 0.4798(2) 0.41924(16) 0.89664(6) 0.0186(4) Uani 1 1 d . . . 
C33 C 0.4138(2) 0.32636(17) 0.86613(6) 0.0214(4) Uani 1 1 d . . . 
C34 C 0.5348(3) 0.38145(15) 0.94079(6) 0.0213(4) Uani 1 1 d . . . 
N1 N 0.4331(2) 0.98793(15) 0.76429(5) 0.0291(4) Uani 1 1 d . . . 
N2 N 0.6498(2) 1.07594(15) 0.89960(5) 0.0266(4) Uani 1 1 d . . . 
N3 N 0.3609(2) 0.25586(14) 0.84055(6) 0.0301(4) Uani 1 1 d . . . 
N4 N 0.5798(2) 0.35583(15) 0.97664(6) 0.0303(4) Uani 1 1 d . . . 
 
 
_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 1.387(3) . ? 
C1 C18 1.400(2) . ? 
C1 H1 0.9300 . ? 
C2 C3 1.380(3) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.397(3) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.425(3) . ? 
C4 C19 1.428(2) . ? 
C5 C6 1.353(3) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.426(3) . ? 
C6 H6 0.9300 . ? 
C7 C20 1.413(2) . ? 
C7 C8 1.414(2) . ? 
C8 C9 1.365(3) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.419(3) . ? 
C9 H9 0.9300 . ? 
C10 C21 1.415(2) . ? 
C10 C11 1.425(3) . ? 
C11 C12 1.347(3) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.434(3) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.396(3) . ? 
C13 C22 1.426(2) . ? 
C14 C15 1.371(3) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.389(3) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.398(2) . ? 
C16 H16 0.9300 . ? 
C17 C22 1.420(2) . ? 
C17 C18 1.464(2) . ? 
C18 C19 1.420(2) . ? 
C19 C20 1.432(2) . ? 
C20 C21 1.427(2) . ? 
C21 C22 1.429(2) . ? 
C23 C29 1.379(2) . ? 
C23 C24 1.437(2) . ? 
C23 C28 1.445(2) . ? 
C24 C25 1.341(2) . ? 
C24 H24 0.9300 . ? 
C25 C26 1.441(2) . ? 
C25 H25 0.9300 . ? 
C26 C32 1.377(2) . ? 
C26 C27 1.444(2) . ? 
C27 C28 1.340(2) . ? 
C27 H27 0.9300 . ? 
C28 H28 0.9300 . ? 
C29 C31 1.433(3) . ? 
C29 C30 1.437(2) . ? 
C30 N1 1.144(2) . ? 
C31 N2 1.150(2) . ? 
C32 C34 1.433(3) . ? 
C32 C33 1.436(3) . ? 
C33 N3 1.143(2) . ? 
C34 N4 1.149(2) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2 C1 C18 121.47(17) . . ? 
C2 C1 H1 119.3 . . ? 
C18 C1 H1 119.3 . . ? 
C3 C2 C1 120.41(17) . . ? 
C3 C2 H2 119.8 . . ? 
C1 C2 H2 119.8 . . ? 
C2 C3 C4 120.79(17) . . ? 
C2 C3 H3 119.6 . . ? 
C4 C3 H3 119.6 . . ? 
C3 C4 C5 122.09(17) . . ? 
C3 C4 C19 119.01(16) . . ? 
C5 C4 C19 118.90(16) . . ? 
C6 C5 C4 121.90(17) . . ? 
C6 C5 H5 119.1 . . ? 
C4 C5 H5 119.1 . . ? 
C5 C6 C7 120.70(17) . . ? 
C5 C6 H6 119.6 . . ? 
C7 C6 H6 119.6 . . ? 
C20 C7 C8 118.69(16) . . ? 
C20 C7 C6 119.34(16) . . ? 
C8 C7 C6 121.92(16) . . ? 
C9 C8 C7 121.44(17) . . ? 
C9 C8 H8 119.3 . . ? 
C7 C8 H8 119.3 . . ? 
C8 C9 C10 121.18(17) . . ? 
C8 C9 H9 119.4 . . ? 
C10 C9 H9 119.4 . . ? 
C21 C10 C9 118.79(17) . . ? 
C21 C10 C11 118.95(17) . . ? 
C9 C10 C11 122.25(16) . . ? 
C12 C11 C10 121.22(17) . . ? 
C12 C11 H11 119.4 . . ? 
C10 C11 H11 119.4 . . ? 
C11 C12 C13 121.58(17) . . ? 
C11 C12 H12 119.2 . . ? 
C13 C12 H12 119.2 . . ? 
C14 C13 C22 119.08(16) . . ? 
C14 C13 C12 122.16(17) . . ? 
C22 C13 C12 118.76(16) . . ? 
C15 C14 C13 120.58(17) . . ? 
C15 C14 H14 119.7 . . ? 
C13 C14 H14 119.7 . . ? 
C14 C15 C16 121.05(17) . . ? 
C14 C15 H15 119.5 . . ? 
C16 C15 H15 119.5 . . ? 
C15 C16 C17 120.83(17) . . ? 
C15 C16 H16 119.6 . . ? 
C17 C16 H16 119.6 . . ? 
C16 C17 C22 118.49(16) . . ? 
C16 C17 C18 122.38(15) . . ? 
C22 C17 C18 119.13(15) . . ? 
C1 C18 C19 118.25(16) . . ? 
C1 C18 C17 122.49(16) . . ? 
C19 C18 C17 119.26(15) . . ? 
C18 C19 C4 120.06(15) . . ? 
C18 C19 C20 121.00(15) . . ? 
C4 C19 C20 118.94(15) . . ? 
C7 C20 C21 120.14(15) . . ? 
C7 C20 C19 120.21(15) . . ? 
C21 C20 C19 119.65(15) . . ? 
C10 C21 C20 119.67(16) . . ? 
C10 C21 C22 120.38(16) . . ? 
C20 C21 C22 119.95(15) . . ? 
C17 C22 C13 119.94(15) . . ? 
C17 C22 C21 121.00(15) . . ? 
C13 C22 C21 119.06(15) . . ? 
C29 C23 C24 120.32(15) . . ? 
C29 C23 C28 122.09(15) . . ? 
C24 C23 C28 117.59(15) . . ? 
C25 C24 C23 121.43(15) . . ? 
C25 C24 H24 119.3 . . ? 
C23 C24 H24 119.3 . . ? 
C24 C25 C26 121.14(15) . . ? 
C24 C25 H25 119.4 . . ? 
C26 C25 H25 119.4 . . ? 
C32 C26 C25 120.93(15) . . ? 
C32 C26 C27 121.59(16) . . ? 
C25 C26 C27 117.48(15) . . ? 
C28 C27 C26 121.35(16) . . ? 
C28 C27 H27 119.3 . . ? 
C26 C27 H27 119.3 . . ? 
C27 C28 C23 121.01(15) . . ? 
C27 C28 H28 119.5 . . ? 
C23 C28 H28 119.5 . . ? 
C23 C29 C31 120.85(15) . . ? 
C23 C29 C30 122.24(16) . . ? 
C31 C29 C30 116.91(15) . . ? 
N1 C30 C29 179.3(2) . . ? 
N2 C31 C29 178.30(19) . . ? 
C26 C32 C34 121.62(16) . . ? 
C26 C32 C33 120.22(16) . . ? 
C34 C32 C33 118.15(16) . . ? 
N3 C33 C32 177.3(2) . . ? 
N4 C34 C32 177.36(19) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.232 
_refine_diff_density_min   -0.259 
_refine_diff_density_rms    0.042 
