 
data_benzo-ghi-perylene-100K
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             benzo[ghi]perylene
_chemical_formula_moiety          'C22 H12' 
_chemical_formula_sum 
 'C22 H12' 
_chemical_formula_weight          276.34 
 
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' 
 
_symmetry_cell_setting           'Monoclinic'
_symmetry_space_group_name_H-M   'P2(1)/c  '
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    9.7377(8) 
_cell_length_b                    11.9539(10) 
_cell_length_c                    11.3813(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.968(1) 
_cell_angle_gamma                 90.00 
_cell_volume                      1312.03(19) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used    4215
_cell_measurement_theta_min        2.48
_cell_measurement_theta_max       28.20
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'yellow'
_exptl_crystal_size_max           0.49 
_exptl_crystal_size_mid           0.37 
_exptl_crystal_size_min           0.25 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.399 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              576 
_exptl_absorpt_coefficient_mu     0.079 
_exptl_absorpt_correction_type    numerical
_exptl_absorpt_correction_T_min   0.9622 
_exptl_absorpt_correction_T_max   0.9806 
_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             6757 
_diffrn_reflns_av_R_equivalents   0.0114 
_diffrn_reflns_av_sigmaI/netI     0.0145 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          2.11 
_diffrn_reflns_theta_max          26.37 
_reflns_number_total              2672 
_reflns_number_gt                 2305 
_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)+(0.0755P)²+0.2657P] 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_number_reflns          2672 
_refine_ls_number_parameters      199 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0453 
_refine_ls_R_factor_gt            0.0401 
_refine_ls_wR_factor_ref          0.1267 
_refine_ls_wR_factor_gt           0.1205 
_refine_ls_goodness_of_fit_ref    1.048 
_refine_ls_restrained_S_all       1.048 
_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 0.72511(11) 0.34781(9) 0.51480(10) 0.0246(3) Uani 1 1 d . . . 
H1 H 0.6890 0.4059 0.4656 0.030 Uiso 1 1 calc R . . 
C2 C 0.86613(11) 0.34646(9) 0.55763(10) 0.0286(3) Uani 1 1 d . . . 
H2 H 0.9226 0.4039 0.5371 0.034 Uiso 1 1 calc R . . 
C3 C 0.92318(11) 0.26118(9) 0.62993(10) 0.0264(3) Uani 1 1 d . . . 
H3 H 1.0175 0.2618 0.6581 0.032 Uiso 1 1 calc R . . 
C4 C 0.83969(10) 0.17355(9) 0.66114(9) 0.0219(3) Uani 1 1 d . . . 
C5 C 0.89627(11) 0.08189(9) 0.73339(9) 0.0249(3) Uani 1 1 d . . . 
H5 H 0.9908 0.0805 0.7608 0.030 Uiso 1 1 calc R . . 
C6 C 0.81512(11) -0.00228(9) 0.76236(9) 0.0247(3) Uani 1 1 d . . . 
H6 H 0.8548 -0.0608 0.8090 0.030 Uiso 1 1 calc R . . 
C7 C 0.66893(11) -0.00331(8) 0.72265(9) 0.0214(2) Uani 1 1 d . . . 
C8 C 0.58310(11) -0.09140(9) 0.75175(9) 0.0252(3) Uani 1 1 d . . . 
H8 H 0.6219 -0.1505 0.7981 0.030 Uiso 1 1 calc R . . 
C9 C 0.44378(11) -0.09117(9) 0.71290(9) 0.0247(3) Uani 1 1 d . . . 
H9 H 0.3895 -0.1503 0.7330 0.030 Uiso 1 1 calc R . . 
C10 C 0.38106(11) -0.00279(9) 0.64276(9) 0.0208(2) Uani 1 1 d . . . 
C11 C 0.23520(11) -0.00109(9) 0.60218(9) 0.0238(3) Uani 1 1 d . . . 
H11 H 0.1799 -0.0595 0.6223 0.029 Uiso 1 1 calc R . . 
C12 C 0.17659(10) 0.08428(9) 0.53493(9) 0.0240(3) Uani 1 1 d . . . 
H12 H 0.0814 0.0839 0.5105 0.029 Uiso 1 1 calc R . . 
C13 C 0.25821(10) 0.17532(9) 0.50065(9) 0.0214(2) Uani 1 1 d . . . 
C14 C 0.19876(11) 0.26319(9) 0.42948(9) 0.0257(3) Uani 1 1 d . . . 
H14 H 0.1036 0.2642 0.4051 0.031 Uiso 1 1 calc R . . 
C15 C 0.28037(11) 0.34819(9) 0.39528(10) 0.0274(3) Uani 1 1 d . . . 
H15 H 0.2397 0.4057 0.3475 0.033 Uiso 1 1 calc R . . 
C16 C 0.42311(11) 0.34891(9) 0.43148(10) 0.0240(3) Uani 1 1 d . . . 
H16 H 0.4764 0.4070 0.4074 0.029 Uiso 1 1 calc R . . 
C17 C 0.48740(10) 0.26409(8) 0.50313(9) 0.0194(2) Uani 1 1 d . . . 
C18 C 0.63701(10) 0.26345(8) 0.54437(9) 0.0195(2) Uani 1 1 d . . . 
C19 C 0.69498(10) 0.17473(8) 0.61871(9) 0.0187(2) Uani 1 1 d . . . 
C20 C 0.60951(10) 0.08563(8) 0.65133(8) 0.0183(2) Uani 1 1 d . . . 
C21 C 0.46440(10) 0.08597(8) 0.61111(9) 0.0184(2) Uani 1 1 d . . . 
C22 C 0.40379(10) 0.17576(8) 0.53830(9) 0.0186(2) 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 1.3921(14) . ? 
C1 C18 1.3951(14) . ? 
C1 H1 0.9300 . ? 
C2 C3 1.3778(16) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.4016(15) . ? 
C3 H3 0.9300 . ? 
C4 C19 1.4249(14) . ? 
C4 C5 1.4334(15) . ? 
C5 C6 1.3483(16) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.4327(14) . ? 
C6 H6 0.9300 . ? 
C7 C8 1.4120(15) . ? 
C7 C20 1.4121(14) . ? 
C8 C9 1.3674(15) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.4111(15) . ? 
C9 H9 0.9300 . ? 
C10 C21 1.4125(14) . ? 
C10 C11 1.4316(14) . ? 
C11 C12 1.3535(15) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.4333(15) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.4016(15) . ? 
C13 C22 1.4229(14) . ? 
C14 C15 1.3789(15) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.3939(14) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.3940(14) . ? 
C16 H16 0.9300 . ? 
C17 C22 1.4243(14) . ? 
C17 C18 1.4674(14) . ? 
C18 C19 1.4238(14) . ? 
C19 C20 1.4319(14) . ? 
C20 C21 1.4237(14) . ? 
C21 C22 1.4323(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 
C2 C1 C18 121.12(10) . . ? 
C2 C1 H1 119.4 . . ? 
C18 C1 H1 119.4 . . ? 
C3 C2 C1 120.95(10) . . ? 
C3 C2 H2 119.5 . . ? 
C1 C2 H2 119.5 . . ? 
C2 C3 C4 120.29(10) . . ? 
C2 C3 H3 119.9 . . ? 
C4 C3 H3 119.9 . . ? 
C3 C4 C19 119.20(10) . . ? 
C3 C4 C5 121.76(10) . . ? 
C19 C4 C5 119.04(9) . . ? 
C6 C5 C4 121.27(9) . . ? 
C6 C5 H5 119.4 . . ? 
C4 C5 H5 119.4 . . ? 
C5 C6 C7 121.31(10) . . ? 
C5 C6 H6 119.3 . . ? 
C7 C6 H6 119.3 . . ? 
C8 C7 C20 119.19(9) . . ? 
C8 C7 C6 121.80(9) . . ? 
C20 C7 C6 119.01(9) . . ? 
C9 C8 C7 121.04(10) . . ? 
C9 C8 H8 119.5 . . ? 
C7 C8 H8 119.5 . . ? 
C8 C9 C10 121.11(10) . . ? 
C8 C9 H9 119.4 . . ? 
C10 C9 H9 119.4 . . ? 
C9 C10 C21 119.19(9) . . ? 
C9 C10 C11 121.69(9) . . ? 
C21 C10 C11 119.11(9) . . ? 
C12 C11 C10 120.99(9) . . ? 
C12 C11 H11 119.5 . . ? 
C10 C11 H11 119.5 . . ? 
C11 C12 C13 121.34(9) . . ? 
C11 C12 H12 119.3 . . ? 
C13 C12 H12 119.3 . . ? 
C14 C13 C22 119.06(9) . . ? 
C14 C13 C12 121.74(9) . . ? 
C22 C13 C12 119.19(9) . . ? 
C15 C14 C13 120.49(9) . . ? 
C15 C14 H14 119.8 . . ? 
C13 C14 H14 119.8 . . ? 
C14 C15 C16 120.74(10) . . ? 
C14 C15 H15 119.6 . . ? 
C16 C15 H15 119.6 . . ? 
C15 C16 C17 121.13(10) . . ? 
C15 C16 H16 119.4 . . ? 
C17 C16 H16 119.4 . . ? 
C16 C17 C22 118.41(9) . . ? 
C16 C17 C18 122.44(9) . . ? 
C22 C17 C18 119.15(9) . . ? 
C1 C18 C19 118.39(9) . . ? 
C1 C18 C17 122.38(9) . . ? 
C19 C18 C17 119.22(9) . . ? 
C18 C19 C4 120.05(9) . . ? 
C18 C19 C20 120.75(9) . . ? 
C4 C19 C20 119.20(9) . . ? 
C7 C20 C21 119.75(9) . . ? 
C7 C20 C19 120.17(9) . . ? 
C21 C20 C19 120.08(9) . . ? 
C10 C21 C20 119.71(9) . . ? 
C10 C21 C22 120.34(9) . . ? 
C20 C21 C22 119.95(9) . . ? 
C13 C22 C17 120.17(9) . . ? 
C13 C22 C21 119.01(9) . . ? 
C17 C22 C21 120.82(9) . . ? 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.226 
_refine_diff_density_min   -0.206 
_refine_diff_density_rms    0.045 
