# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bper-TCNQ-100K
_database_code_depnum_ccdc_archive 'CCDC 1537813'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bper2TCNQ-100K
_database_code_depnum_ccdc_archive 'CCDC 1537814'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (benzo[ghi]perylene)2TCNQ
_chemical_formula_moiety         '(C22 H12), (C12 H4 N4)'
_chemical_formula_sum            'C56 H28 N4'
_chemical_formula_weight         756.87

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                   7.1246(8)
_cell_length_b                   12.3495(14)
_cell_length_c                   21.257(3)
_cell_angle_alpha                78.598(2)
_cell_angle_beta                 80.637(2)
_cell_angle_gamma                80.207(2)
_cell_volume                     1790.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3082
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.03

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_T_max  0.9942
_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            16922
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_sigmaI/netI    0.1143
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.02
_reflns_number_total             6295
_reflns_number_gt                3197
_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)+(0.0757P)²+0.0000P] 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         6295
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.1755
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.7540(5) 0.1065(3) 0.33586(17) 0.0209(9) Uani 1 1 d . . .
H1 H 0.8236 0.0495 0.3153 0.025 Uiso 1 1 calc R . .
C2 C 0.7231(5) 0.0904(3) 0.40326(17) 0.0245(10) Uani 1 1 d . . .
H2 H 0.7724 0.0230 0.4271 0.029 Uiso 1 1 calc R . .
C3 C 0.6203(5) 0.1731(3) 0.43504(18) 0.0249(10) Uani 1 1 d . . .
H3 H 0.5998 0.1611 0.4801 0.030 Uiso 1 1 calc R . .
C4 C 0.5468(5) 0.2749(3) 0.39984(17) 0.0205(9) Uani 1 1 d . . .
C5 C 0.4400(5) 0.3639(4) 0.43168(19) 0.0271(10) Uani 1 1 d . . .
H5 H 0.4204 0.3533 0.4767 0.033 Uiso 1 1 calc R . .
C6 C 0.3687(5) 0.4610(4) 0.39786(18) 0.0263(10) Uani 1 1 d . . .
H6 H 0.3000 0.5164 0.4198 0.032 Uiso 1 1 calc R . .
C7 C 0.3955(5) 0.4816(3) 0.32868(18) 0.0219(9) Uani 1 1 d . . .
C8 C 0.3223(6) 0.5838(3) 0.2926(2) 0.0290(11) Uani 1 1 d . . .
H8 H 0.2541 0.6400 0.3142 0.035 Uiso 1 1 calc R . .
C9 C 0.3498(5) 0.6019(3) 0.2265(2) 0.0274(10) Uani 1 1 d . . .
H9 H 0.2982 0.6698 0.2037 0.033 Uiso 1 1 calc R . .
C10 C 0.4553(5) 0.5193(3) 0.19200(18) 0.0192(9) Uani 1 1 d . . .
C11 C 0.4905(5) 0.5385(3) 0.12257(18) 0.0234(10) Uani 1 1 d . . .
H11 H 0.4418 0.6066 0.0993 0.028 Uiso 1 1 calc R . .
C12 C 0.5939(5) 0.4585(3) 0.09040(18) 0.0215(9) Uani 1 1 d . . .
H12 H 0.6142 0.4729 0.0454 0.026 Uiso 1 1 calc R . .
C13 C 0.6719(5) 0.3532(3) 0.12398(17) 0.0159(9) Uani 1 1 d . . .
C14 C 0.7806(5) 0.2704(3) 0.09179(17) 0.0198(9) Uani 1 1 d . . .
H14 H 0.8033 0.2837 0.0468 0.024 Uiso 1 1 calc R . .
C15 C 0.8544(5) 0.1701(3) 0.12527(17) 0.0196(9) Uani 1 1 d . . .
H15 H 0.9266 0.1161 0.1028 0.024 Uiso 1 1 calc R . .
C16 C 0.8227(5) 0.1481(3) 0.19219(17) 0.0180(9) Uani 1 1 d . . .
H16 H 0.8733 0.0792 0.2141 0.022 Uiso 1 1 calc R . .
C17 C 0.7164(5) 0.2271(3) 0.22741(17) 0.0146(8) Uani 1 1 d . . .
C18 C 0.6825(5) 0.2067(3) 0.29859(17) 0.0166(9) Uani 1 1 d . . .
C19 C 0.5762(5) 0.2929(3) 0.33094(17) 0.0180(9) Uani 1 1 d . . .
C20 C 0.5006(5) 0.3972(3) 0.29533(18) 0.0171(9) Uani 1 1 d . . .
C21 C 0.5307(5) 0.4166(3) 0.22658(17) 0.0154(9) Uani 1 1 d . . .
C22 C 0.6391(5) 0.3314(3) 0.19288(17) 0.0158(9) Uani 1 1 d . . .
C23 C -0.2670(6) 0.7232(3) 0.30849(19) 0.0276(10) Uani 1 1 d . . .
H23 H -0.3553 0.6950 0.2906 0.033 Uiso 1 1 calc R . .
C24 C -0.2753(6) 0.7064(4) 0.37505(19) 0.0330(11) Uani 1 1 d . . .
H24 H -0.3671 0.6664 0.4012 0.040 Uiso 1 1 calc R . .
C25 C -0.1481(6) 0.7486(4) 0.40274(19) 0.0325(11) Uani 1 1 d . . .
H25 H -0.1556 0.7373 0.4476 0.039 Uiso 1 1 calc R . .
C26 C -0.0083(6) 0.8080(3) 0.36456(17) 0.0218(9) Uani 1 1 d . . .
C27 C 0.1293(6) 0.8505(3) 0.39160(19) 0.0269(10) Uani 1 1 d . . .
H27 H 0.1217 0.8416 0.4364 0.032 Uiso 1 1 calc R . .
C28 C 0.2692(6) 0.9030(3) 0.35422(18) 0.0247(10) Uani 1 1 d . . .
H28 H 0.3570 0.9290 0.3734 0.030 Uiso 1 1 calc R . .
C29 C 0.2845(5) 0.9192(3) 0.28532(18) 0.0199(9) Uani 1 1 d . . .
C30 C 0.4343(5) 0.9723(3) 0.24476(18) 0.0240(10) Uani 1 1 d . . .
H30 H 0.5238 0.9979 0.2635 0.029 Uiso 1 1 calc R . .
C31 C 0.4490(5) 0.9863(3) 0.17851(18) 0.0235(10) Uani 1 1 d . . .
H31 H 0.5482 1.0211 0.1530 0.028 Uiso 1 1 calc R . .
C32 C 0.3156(5) 0.9487(3) 0.14875(17) 0.0206(9) Uani 1 1 d . . .
C33 C 0.3316(6) 0.9603(3) 0.08001(18) 0.0255(10) Uani 1 1 d . . .
H33 H 0.4310 0.9945 0.0542 0.031 Uiso 1 1 calc R . .
C34 C 0.2054(5) 0.9224(3) 0.05172(18) 0.0221(10) Uani 1 1 d . . .
H34 H 0.2201 0.9310 0.0068 0.027 Uiso 1 1 calc R . .
C35 C 0.0493(5) 0.8694(3) 0.08899(17) 0.0202(9) Uani 1 1 d . . .
C36 C -0.0837(6) 0.8316(3) 0.06108(18) 0.0226(10) Uani 1 1 d . . .
H36 H -0.0743 0.8422 0.0162 0.027 Uiso 1 1 calc R . .
C37 C -0.2302(6) 0.7785(3) 0.09834(18) 0.0238(10) Uani 1 1 d . . .
H37 H -0.3192 0.7543 0.0787 0.029 Uiso 1 1 calc R . .
C38 C -0.2437(5) 0.7615(3) 0.16501(18) 0.0226(10) Uani 1 1 d . . .
H38 H -0.3410 0.7239 0.1897 0.027 Uiso 1 1 calc R . .
C39 C -0.1176(5) 0.7983(3) 0.19652(17) 0.0185(9) Uani 1 1 d . . .
C40 C -0.1294(5) 0.7814(3) 0.26725(18) 0.0191(9) Uani 1 1 d . . .
C41 C 0.0018(5) 0.8238(3) 0.29580(17) 0.0186(9) Uani 1 1 d . . .
C42 C 0.1514(5) 0.8806(3) 0.25624(17) 0.0180(9) Uani 1 1 d . . .
C43 C 0.1661(5) 0.8950(3) 0.18710(17) 0.0179(9) Uani 1 1 d . . .
C44 C 0.0316(5) 0.8542(3) 0.15793(17) 0.0166(9) Uani 1 1 d . . .
C45 C 0.0640(5) 0.3080(3) 0.32583(17) 0.0158(9) Uani 1 1 d . . .
C46 C -0.0116(5) 0.4134(3) 0.29069(17) 0.0177(9) Uani 1 1 d . . .
H46 H -0.0800 0.4680 0.3134 0.021 Uiso 1 1 calc R . .
C47 C 0.0142(5) 0.4352(3) 0.22532(17) 0.0170(9) Uani 1 1 d . . .
H47 H -0.0373 0.5041 0.2036 0.020 Uiso 1 1 calc R . .
C48 C 0.1214(5) 0.3521(3) 0.18870(17) 0.0162(9) Uani 1 1 d . . .
C49 C 0.1946(5) 0.2463(3) 0.22418(17) 0.0174(9) Uani 1 1 d . . .
H49 H 0.2617 0.1910 0.2018 0.021 Uiso 1 1 calc R . .
C50 C 0.1679(5) 0.2256(3) 0.28909(17) 0.0167(9) Uani 1 1 d . . .
H50 H 0.2179 0.1564 0.3108 0.020 Uiso 1 1 calc R . .
C51 C 0.0377(5) 0.2861(3) 0.39265(17) 0.0168(9) Uani 1 1 d . . .
C52 C -0.0662(6) 0.3654(3) 0.43106(18) 0.0225(10) Uani 1 1 d . . .
C53 C 0.1158(5) 0.1813(4) 0.42798(17) 0.0199(9) Uani 1 1 d . . .
C54 C 0.1529(5) 0.3745(3) 0.12175(16) 0.0157(9) Uani 1 1 d . . .
C55 C 0.0862(5) 0.4802(3) 0.08507(17) 0.0184(9) Uani 1 1 d . . .
C56 C 0.2622(5) 0.2945(3) 0.08434(18) 0.0181(9) Uani 1 1 d . . .
N1 N -0.1496(5) 0.4298(3) 0.46181(15) 0.0304(9) Uani 1 1 d . . .
N2 N 0.1802(5) 0.0977(3) 0.45685(15) 0.0265(8) Uani 1 1 d . . .
N3 N 0.0366(5) 0.5642(3) 0.05402(15) 0.0266(8) Uani 1 1 d . . .
N4 N 0.3508(5) 0.2326(3) 0.05343(15) 0.0254(8) 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 1.393(5) . ?
C1 C18 1.395(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(5) . ?
C3 H3 0.9300 . ?
C4 C19 1.423(5) . ?
C4 C5 1.445(5) . ?
C5 C6 1.335(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(5) . ?
C7 C20 1.416(5) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.413(5) . ?
C9 H9 0.9300 . ?
C10 C21 1.402(5) . ?
C10 C11 1.435(5) . ?
C11 C12 1.357(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.424(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.396(5) . ?
C13 C22 1.423(5) . ?
C14 C15 1.367(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.421(5) . ?
C17 C18 1.470(5) . ?
C18 C19 1.424(5) . ?
C19 C20 1.426(5) . ?
C20 C21 1.420(5) . ?
C21 C22 1.434(5) . ?
C23 C24 1.382(5) . ?
C23 C40 1.399(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.393(5) . ?
C25 H25 0.9300 . ?
C26 C41 1.427(5) . ?
C26 C27 1.430(5) . ?
C27 C28 1.343(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.427(5) . ?
C28 H28 0.9300 . ?
C29 C42 1.403(5) . ?
C29 C30 1.424(5) . ?
C30 C31 1.373(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.407(5) . ?
C31 H31 0.9300 . ?
C32 C43 1.408(5) . ?
C32 C33 1.427(5) . ?
C33 C34 1.349(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.431(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.383(5) . ?
C35 C44 1.428(5) . ?
C36 C37 1.380(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.381(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.385(5) . ?
C38 H38 0.9300 . ?
C39 C44 1.422(5) . ?
C39 C40 1.467(5) . ?
C40 C41 1.412(5) . ?
C41 C42 1.436(5) . ?
C42 C43 1.434(5) . ?
C43 C44 1.427(5) . ?
C45 C51 1.380(5) . ?
C45 C46 1.432(5) . ?
C45 C50 1.436(5) . ?
C46 C47 1.350(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.448(5) . ?
C47 H47 0.9300 . ?
C48 C54 1.383(5) . ?
C48 C49 1.434(5) . ?
C49 C50 1.341(5) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C52 1.430(5) . ?
C51 C53 1.433(5) . ?
C52 N1 1.155(4) . ?
C53 N2 1.155(5) . ?
C54 C55 1.430(5) . ?
C54 C56 1.436(5) . ?
C55 N3 1.147(5) . ?
C56 N4 1.147(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 C18 121.2(4) . . ?
C2 C1 H1 119.4 . . ?
C18 C1 H1 119.4 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C19 120.0(4) . . ?
C3 C4 C5 121.5(3) . . ?
C19 C4 C5 118.4(4) . . ?
C6 C5 C4 121.4(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.5(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C20 118.9(4) . . ?
C8 C7 C6 121.9(4) . . ?
C20 C7 C6 119.1(4) . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C21 C10 C9 119.1(4) . . ?
C21 C10 C11 119.1(3) . . ?
C9 C10 C11 121.8(4) . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C22 118.6(3) . . ?
C14 C13 C12 122.4(3) . . ?
C22 C13 C12 119.0(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 121.3(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C22 118.3(3) . . ?
C16 C17 C18 122.5(3) . . ?
C22 C17 C18 119.1(3) . . ?
C1 C18 C19 118.5(3) . . ?
C1 C18 C17 122.5(3) . . ?
C19 C18 C17 119.0(3) . . ?
C4 C19 C18 119.4(4) . . ?
C4 C19 C20 119.7(4) . . ?
C18 C19 C20 121.0(3) . . ?
C7 C20 C21 120.0(4) . . ?
C7 C20 C19 119.8(3) . . ?
C21 C20 C19 120.2(3) . . ?
C10 C21 C20 119.8(3) . . ?
C10 C21 C22 120.3(3) . . ?
C20 C21 C22 119.9(3) . . ?
C17 C22 C13 120.0(3) . . ?
C17 C22 C21 120.8(3) . . ?
C13 C22 C21 119.2(3) . . ?
C24 C23 C40 121.8(4) . . ?
C24 C23 H23 119.1 . . ?
C40 C23 H23 119.1 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 121.0(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C41 118.7(4) . . ?
C25 C26 C27 122.5(4) . . ?
C41 C26 C27 118.8(4) . . ?
C28 C27 C26 121.9(4) . . ?
C28 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
C27 C28 C29 120.7(4) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C42 C29 C30 118.6(3) . . ?
C42 C29 C28 119.8(4) . . ?
C30 C29 C28 121.6(4) . . ?
C31 C30 C29 121.1(4) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 120.8(4) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C31 C32 C43 119.9(3) . . ?
C31 C32 C33 121.5(4) . . ?
C43 C32 C33 118.6(4) . . ?
C34 C33 C32 121.3(4) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 121.8(4) . . ?
C33 C34 H34 119.1 . . ?
C35 C34 H34 119.1 . . ?
C36 C35 C44 118.7(4) . . ?
C36 C35 C34 122.8(4) . . ?
C44 C35 C34 118.4(3) . . ?
C37 C36 C35 121.5(4) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C36 C37 C38 119.5(4) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C39 122.4(4) . . ?
C37 C38 H38 118.8 . . ?
C39 C38 H38 118.8 . . ?
C38 C39 C44 117.9(3) . . ?
C38 C39 C40 123.3(4) . . ?
C44 C39 C40 118.8(3) . . ?
C23 C40 C41 117.8(4) . . ?
C23 C40 C39 122.2(4) . . ?
C41 C40 C39 120.0(3) . . ?
C40 C41 C26 120.5(4) . . ?
C40 C41 C42 120.6(3) . . ?
C26 C41 C42 118.8(3) . . ?
C29 C42 C43 120.4(4) . . ?
C29 C42 C41 120.0(3) . . ?
C43 C42 C41 119.5(3) . . ?
C32 C43 C44 120.8(3) . . ?
C32 C43 C42 119.1(3) . . ?
C44 C43 C42 120.1(3) . . ?
C39 C44 C43 120.9(3) . . ?
C39 C44 C35 120.0(3) . . ?
C43 C44 C35 119.1(3) . . ?
C51 C45 C46 121.2(3) . . ?
C51 C45 C50 121.1(3) . . ?
C46 C45 C50 117.7(3) . . ?
C47 C46 C45 121.4(4) . . ?
C47 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?
C46 C47 C48 120.6(4) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C54 C48 C49 121.2(3) . . ?
C54 C48 C47 121.1(3) . . ?
C49 C48 C47 117.8(3) . . ?
C50 C49 C48 121.1(4) . . ?
C50 C49 H49 119.4 . . ?
C48 C49 H49 119.4 . . ?
C49 C50 C45 121.5(4) . . ?
C49 C50 H50 119.3 . . ?
C45 C50 H50 119.3 . . ?
C45 C51 C52 122.9(3) . . ?
C45 C51 C53 121.4(3) . . ?
C52 C51 C53 115.7(3) . . ?
N1 C52 C51 179.6(5) . . ?
N2 C53 C51 179.1(4) . . ?
C48 C54 C55 122.5(3) . . ?
C48 C54 C56 122.2(3) . . ?
C55 C54 C56 115.3(3) . . ?
N3 C55 C54 177.9(4) . . ?
N4 C56 C54 178.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_benzo-ghi-perylene-100K
_database_code_depnum_ccdc_archive 'CCDC 1537817'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bper3TCNQ-100K
_database_code_depnum_ccdc_archive 'CCDC 1537815'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (benzo[ghi]perylene)3TCNQ
_chemical_formula_moiety         '(C22 H12), (C12 H4 N4)'
_chemical_formula_sum            'C78 H40 N4'
_chemical_formula_weight         1033.20

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                   10.0725(14)
_cell_length_b                   10.8786(15)
_cell_length_c                   12.9332(18)
_cell_angle_alpha                113.110(2)
_cell_angle_beta                 105.578(2)
_cell_angle_gamma                90.301(2)
_cell_volume                     1245.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3670
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.07

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_T_max  0.9968
_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            13202
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         26.36
_reflns_number_total             5057
_reflns_number_gt                3124
_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)+(0.0603P)²+0.0000P] 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         5057
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.73119(17) -0.08386(19) 0.27129(16) 0.0336(4) Uani 1 1 d . . .
H1 H 0.7646 -0.0350 0.3523 0.040 Uiso 1 1 calc R . .
C2 C 0.69106(17) -0.22071(19) 0.22721(17) 0.0377(5) Uani 1 1 d . . .
H2 H 0.6968 -0.2621 0.2787 0.045 Uiso 1 1 calc R . .
C3 C 0.64291(16) -0.29620(18) 0.10822(17) 0.0340(4) Uani 1 1 d . . .
H3 H 0.6161 -0.3882 0.0798 0.041 Uiso 1 1 calc R . .
C4 C 0.63381(15) -0.23605(16) 0.02923(15) 0.0270(4) Uani 1 1 d . . .
C5 C 0.58573(15) -0.31163(17) -0.09517(16) 0.0318(4) Uani 1 1 d . . .
H5 H 0.5613 -0.4042 -0.1250 0.038 Uiso 1 1 calc R . .
C6 C 0.57488(15) -0.25221(17) -0.17062(15) 0.0297(4) Uani 1 1 d . . .
H6 H 0.5421 -0.3043 -0.2511 0.036 Uiso 1 1 calc R . .
C7 C 0.61281(14) -0.11096(16) -0.12907(14) 0.0246(4) Uani 1 1 d . . .
C8 C 0.60042(15) -0.04654(18) -0.20614(14) 0.0301(4) Uani 1 1 d . . .
H8 H 0.5663 -0.0973 -0.2868 0.036 Uiso 1 1 calc R . .
C9 C 0.63735(15) 0.08871(18) -0.16499(14) 0.0293(4) Uani 1 1 d . . .
H9 H 0.6282 0.1283 -0.2181 0.035 Uiso 1 1 calc R . .
C10 C 0.68912(15) 0.16960(16) -0.04336(14) 0.0246(4) Uani 1 1 d . . .
C11 C 0.72935(15) 0.31118(17) 0.00146(15) 0.0297(4) Uani 1 1 d . . .
H11 H 0.7225 0.3520 -0.0506 0.036 Uiso 1 1 calc R . .
C12 C 0.77716(15) 0.38647(17) 0.11841(16) 0.0309(4) Uani 1 1 d . . .
H12 H 0.8041 0.4782 0.1452 0.037 Uiso 1 1 calc R . .
C13 C 0.78756(15) 0.32927(16) 0.20216(15) 0.0271(4) Uani 1 1 d . . .
C14 C 0.83218(16) 0.40794(18) 0.32299(16) 0.0357(4) Uani 1 1 d . . .
H14 H 0.8579 0.5001 0.3508 0.043 Uiso 1 1 calc R . .
C15 C 0.83842(17) 0.35016(19) 0.40113(16) 0.0397(5) Uani 1 1 d . . .
H15 H 0.8665 0.4038 0.4815 0.048 Uiso 1 1 calc R . .
C16 C 0.80336(16) 0.21304(18) 0.36155(14) 0.0331(4) Uani 1 1 d . . .
H16 H 0.8086 0.1762 0.4162 0.040 Uiso 1 1 calc R . .
C17 C 0.76020(14) 0.12827(16) 0.24185(14) 0.0248(4) Uani 1 1 d . . .
C18 C 0.72301(14) -0.01700(16) 0.19764(14) 0.0245(4) Uani 1 1 d . . .
C19 C 0.67405(14) -0.09491(15) 0.07408(14) 0.0223(4) Uani 1 1 d . . .
C20 C 0.66274(14) -0.03253(15) -0.00655(13) 0.0207(4) Uani 1 1 d . . .
C21 C 0.70110(14) 0.10861(15) 0.03638(13) 0.0211(3) Uani 1 1 d . . .
C22 C 0.75037(14) 0.18826(15) 0.16055(13) 0.0226(4) Uani 1 1 d . . .
C31 C 0.4748(6) 0.6841(6) 0.4359(4) 0.0308(10) Uani 0.50 1 d P A -1
H31 H 0.3914 0.6272 0.4014 0.037 Uiso 0.50 1 calc PR A -1
C32 C 0.5966(5) 0.6316(5) 0.4633(4) 0.0367(12) Uani 0.50 1 d P A -1
H32 H 0.5946 0.5401 0.4464 0.044 Uiso 0.50 1 calc PR A -1
C33 C 0.7238(7) 0.7153(6) 0.5166(5) 0.0276(11) Uani 0.50 1 d P A -1
H33 H 0.8054 0.6792 0.5365 0.033 Uiso 0.50 1 calc PR A -1
C34 C 0.7293(6) 0.8523(8) 0.5400(4) 0.0258(10) Uani 0.50 1 d P A -1
C35 C 0.8569(7) 0.9397(6) 0.5928(4) 0.0255(11) Uani 0.50 1 d P A -1
H35 H 0.9402 0.9043 0.6083 0.031 Uiso 0.50 1 calc PR A -1
C36 C 0.8588(5) 1.0734(6) 0.6207(4) 0.0286(10) Uani 0.50 1 d P A -1
H36 H 0.9436 1.1282 0.6548 0.034 Uiso 0.50 1 calc PR A -1
C37 C 0.7325(7) 1.1328(6) 0.5988(4) 0.0221(9) Uani 0.50 1 d P A -1
C38 C 0.7352(4) 1.2730(4) 0.6322(3) 0.0297(8) Uani 0.50 1 d P A -1
H38 H 0.8192 1.3289 0.6712 0.036 Uiso 0.50 1 calc PR A -1
C39 C 0.6142(4) 1.3271(4) 0.6073(3) 0.0305(8) Uani 0.50 1 d P A -1
H39 H 0.6169 1.4196 0.6294 0.037 Uiso 0.50 1 calc PR A -1
C40 C 0.4866(5) 1.2447(7) 0.5491(4) 0.0267(10) Uani 0.50 1 d P A -1
C41 C 0.3593(6) 1.2991(6) 0.5188(4) 0.0322(11) Uani 0.50 1 d P A -1
H41 H 0.3616 1.3907 0.5361 0.039 Uiso 0.50 1 calc PR A -1
C42 C 0.2352(6) 1.2181(7) 0.4651(4) 0.0275(11) Uani 0.50 1 d P A -1
H42 H 0.1547 1.2562 0.4467 0.033 Uiso 0.50 1 calc PR A -1
C43 C 0.2249(8) 1.0777(7) 0.4364(4) 0.0258(10) Uani 0.50 1 d P A -1
C44 C 0.0991(6) 0.9944(7) 0.3812(4) 0.0279(12) Uani 0.50 1 d P A -1
H44 H 0.0171 1.0311 0.3640 0.034 Uiso 0.50 1 calc PR A -1
C45 C 0.0948(5) 0.8573(5) 0.3516(4) 0.0314(11) Uani 0.50 1 d P A -1
H45 H 0.0096 0.8031 0.3161 0.038 Uiso 0.50 1 calc PR A -1
C46 C 0.2154(5) 0.7998(6) 0.3740(4) 0.0275(10) Uani 0.50 1 d P A -1
H46 H 0.2109 0.7070 0.3506 0.033 Uiso 0.50 1 calc PR A -1
C47 C 0.3464(7) 0.8815(7) 0.4327(4) 0.0221(9) Uani 0.50 1 d P A -1
C48 C 0.4731(5) 0.8216(8) 0.4588(4) 0.0246(10) Uani 0.50 1 d P A -1
C49 C 0.6008(8) 0.9062(7) 0.5118(4) 0.0191(8) Uani 0.50 1 d P A -1
C50 C 0.6067(5) 1.0461(8) 0.5422(4) 0.0219(9) Uani 0.50 1 d P A -1
C51 C 0.4799(8) 1.1062(6) 0.5182(4) 0.0196(9) Uani 0.50 1 d P A -1
C52 C 0.3509(5) 1.0202(8) 0.4616(4) 0.0211(9) Uani 0.50 1 d P A -1
C61 C 0.96533(14) 0.86047(15) 0.96512(14) 0.0224(4) Uani 1 1 d . . .
C62 C 1.01837(14) 0.95055(16) 1.08734(13) 0.0225(4) Uani 1 1 d . . .
H62 H 1.0301 0.9165 1.1444 0.027 Uiso 1 1 calc R . .
C63 C 0.94870(14) 0.91705(16) 0.87956(13) 0.0231(4) Uani 1 1 d . . .
H63 H 0.9146 0.8610 0.8000 0.028 Uiso 1 1 calc R . .
C64 C 0.93283(15) 0.72463(16) 0.93201(15) 0.0277(4) Uani 1 1 d . . .
C65 C 0.94808(17) 0.67059(17) 1.01870(18) 0.0354(4) Uani 1 1 d . . .
C66 C 0.88373(17) 0.63403(18) 0.81033(19) 0.0377(5) Uani 1 1 d . . .
N1 N 0.96167(16) 0.63162(16) 1.09094(17) 0.0500(5) Uani 1 1 d . . .
N2 N 0.84600(16) 0.56592(17) 0.71179(16) 0.0591(5) 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 1.381(2) . ?
C1 C18 1.395(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9300 . ?
C4 C19 1.423(2) . ?
C4 C5 1.427(2) . ?
C5 C6 1.349(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.425(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.408(2) . ?
C7 C20 1.414(2) . ?
C8 C9 1.364(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.410(2) . ?
C9 H9 0.9300 . ?
C10 C21 1.410(2) . ?
C10 C11 1.428(2) . ?
C11 C12 1.350(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.428(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(2) . ?
C13 C22 1.421(2) . ?
C14 C15 1.373(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(2) . ?
C16 H16 0.9300 . ?
C17 C22 1.423(2) . ?
C17 C18 1.461(2) . ?
C18 C19 1.423(2) . ?
C19 C20 1.433(2) . ?
C20 C21 1.423(2) . ?
C21 C22 1.432(2) . ?
C31 C32 1.374(7) . ?
C31 C48 1.408(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.402(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.397(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.425(6) . ?
C34 C49 1.440(8) . ?
C35 C36 1.353(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.441(7) . ?
C36 H36 0.9300 . ?
C37 C50 1.407(6) . ?
C37 C38 1.411(6) . ?
C38 C39 1.371(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.400(6) . ?
C39 H39 0.9300 . ?
C40 C51 1.395(7) . ?
C40 C41 1.438(8) . ?
C41 C42 1.365(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.419(7) . ?
C42 H42 0.9300 . ?
C43 C44 1.389(7) . ?
C43 C52 1.434(8) . ?
C44 C45 1.384(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.383(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.423(7) . ?
C46 H46 0.9300 . ?
C47 C52 1.402(7) . ?
C47 C48 1.455(7) . ?
C48 C49 1.411(7) . ?
C49 C50 1.411(7) . ?
C50 C51 1.453(6) . ?
C51 C52 1.428(6) . ?
C61 C64 1.377(2) . ?
C61 C63 1.438(2) . ?
C61 C62 1.438(2) . ?
C62 C63 1.343(2) 2_777 ?
C62 H62 0.9300 . ?
C63 C62 1.343(2) 2_777 ?
C63 H63 0.9300 . ?
C64 C66 1.432(3) . ?
C64 C65 1.432(3) . ?
C65 N1 1.146(2) . ?
C66 N2 1.146(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 121.80(17) . . ?
C2 C1 H1 119.1 . . ?
C18 C1 H1 119.1 . . ?
C3 C2 C1 120.66(17) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.58(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C19 119.05(16) . . ?
C3 C4 C5 122.15(16) . . ?
C19 C4 C5 118.80(15) . . ?
C6 C5 C4 121.68(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 121.15(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C20 118.83(15) . . ?
C8 C7 C6 122.11(15) . . ?
C20 C7 C6 119.05(15) . . ?
C9 C8 C7 121.40(15) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 121.20(15) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C21 118.88(15) . . ?
C9 C10 C11 122.06(15) . . ?
C21 C10 C11 119.06(15) . . ?
C12 C11 C10 120.82(15) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.89(16) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C22 119.39(16) . . ?
C14 C13 C12 121.85(16) . . ?
C22 C13 C12 118.76(15) . . ?
C15 C14 C13 120.38(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.64(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 121.85(17) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C22 117.65(16) . . ?
C16 C17 C18 122.97(15) . . ?
C22 C17 C18 119.37(14) . . ?
C1 C18 C19 117.81(15) . . ?
C1 C18 C17 122.98(15) . . ?
C19 C18 C17 119.20(14) . . ?
C18 C19 C4 120.10(14) . . ?
C18 C19 C20 120.69(14) . . ?
C4 C19 C20 119.21(14) . . ?
C7 C20 C21 119.76(14) . . ?
C7 C20 C19 120.09(14) . . ?
C21 C20 C19 120.16(14) . . ?
C10 C21 C20 119.92(14) . . ?
C10 C21 C22 120.34(15) . . ?
C20 C21 C22 119.74(14) . . ?
C13 C22 C17 120.05(14) . . ?
C13 C22 C21 119.11(14) . . ?
C17 C22 C21 120.83(15) . . ?
C32 C31 C48 121.8(5) . . ?
C32 C31 H31 119.1 . . ?
C48 C31 H31 119.1 . . ?
C31 C32 C33 120.3(5) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C34 C33 C32 120.7(5) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 122.1(5) . . ?
C33 C34 C49 118.4(6) . . ?
C35 C34 C49 119.5(7) . . ?
C36 C35 C34 121.0(6) . . ?
C36 C35 H35 119.5 . . ?
C34 C35 H35 119.5 . . ?
C35 C36 C37 121.5(5) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C50 C37 C38 121.2(6) . . ?
C50 C37 C36 117.7(4) . . ?
C38 C37 C36 121.1(7) . . ?
C39 C38 C37 120.2(4) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C40 120.7(4) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C51 C40 C39 120.5(6) . . ?
C51 C40 C41 118.0(5) . . ?
C39 C40 C41 121.5(7) . . ?
C42 C41 C40 120.8(5) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C43 122.3(6) . . ?
C41 C42 H42 118.8 . . ?
C43 C42 H42 118.8 . . ?
C44 C43 C42 122.7(5) . . ?
C44 C43 C52 119.4(6) . . ?
C42 C43 C52 117.9(7) . . ?
C45 C44 C43 120.5(5) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C46 C45 C44 120.9(5) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C45 C46 C47 120.6(5) . . ?
C45 C46 H46 119.7 . . ?
C47 C46 H46 119.7 . . ?
C52 C47 C46 118.5(4) . . ?
C52 C47 C48 120.8(7) . . ?
C46 C47 C48 120.7(6) . . ?
C31 C48 C49 118.2(5) . . ?
C31 C48 C47 123.5(6) . . ?
C49 C48 C47 118.3(7) . . ?
C50 C49 C48 121.4(5) . . ?
C50 C49 C34 118.0(7) . . ?
C48 C49 C34 120.6(5) . . ?
C37 C50 C49 122.2(6) . . ?
C37 C50 C51 117.5(8) . . ?
C49 C50 C51 120.2(4) . . ?
C40 C51 C52 121.7(6) . . ?
C40 C51 C50 119.8(8) . . ?
C52 C51 C50 118.4(4) . . ?
C47 C52 C51 120.8(5) . . ?
C47 C52 C43 120.1(5) . . ?
C51 C52 C43 119.1(7) . . ?
C64 C61 C63 121.54(15) . . ?
C64 C61 C62 120.71(15) . . ?
C63 C61 C62 117.74(14) . . ?
C63 C62 C61 121.15(14) 2_777 . ?
C63 C62 H62 119.4 2_777 . ?
C61 C62 H62 119.4 . . ?
C62 C63 C61 121.11(14) 2_777 . ?
C62 C63 H63 119.4 2_777 . ?
C61 C63 H63 119.4 . . ?
C61 C64 C66 120.89(16) . . ?
C61 C64 C65 120.67(16) . . ?
C66 C64 C65 118.44(15) . . ?
N1 C65 C64 177.7(2) . . ?
N2 C66 C64 177.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.040
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bper3Mo6O19-100K
_database_code_depnum_ccdc_archive 'CCDC 1537816'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (benzo[ghi]perylene)3Mo6O19
_chemical_formula_moiety         '(C22 H12), (Mo6 O19)'
_chemical_formula_sum            'C66 H36 Mo6 O19'
_chemical_formula_weight         1708.64

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 '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                   9.8455(9)
_cell_length_b                   11.0998(10)
_cell_length_c                   12.8243(11)
_cell_angle_alpha                86.101(1)
_cell_angle_beta                 67.763(1)
_cell_angle_gamma                89.093(1)
_cell_volume                     1294.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4676
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.14

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    1.499
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4874
_exptl_absorpt_correction_T_max  0.9425
_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            6862
_diffrn_reflns_av_R_equivalents  0.0086
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5122
_reflns_number_gt                4524
_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)+(0.0266P)²+1.0137P] 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         5122
_refine_ls_number_parameters     511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.2336(3) 0.9108(2) 1.1540(2) 0.0203(5) Uani 1 1 d . . .
H1 H 0.2027 0.8340 1.1878 0.024 Uiso 1 1 calc R . .
C2 C 0.2105(3) 1.0084(2) 1.2211(2) 0.0216(5) Uani 1 1 d . . .
H2 H 0.1640 0.9961 1.2990 0.026 Uiso 1 1 calc R . .
C3 C 0.2553(3) 1.1224(2) 1.1737(2) 0.0201(5) Uani 1 1 d . . .
H3 H 0.2393 1.1866 1.2199 0.024 Uiso 1 1 calc R . .
C4 C 0.3256(3) 1.1437(2) 1.0557(2) 0.0179(5) Uani 1 1 d . . .
C5 C 0.3755(3) 1.2600(2) 1.0055(2) 0.0198(5) Uani 1 1 d . . .
H5 H 0.3597 1.3246 1.0511 0.024 Uiso 1 1 calc R . .
C6 C 0.4470(3) 1.2800(2) 0.8905(2) 0.0209(5) Uani 1 1 d . . .
H6 H 0.4797 1.3574 0.8598 0.025 Uiso 1 1 calc R . .
C7 C 0.4713(3) 1.1845(2) 0.8187(2) 0.0198(5) Uani 1 1 d . . .
C8 C 0.5464(3) 1.2033(2) 0.6993(2) 0.0236(5) Uani 1 1 d . . .
H8 H 0.5784 1.2806 0.6675 0.028 Uiso 1 1 calc R . .
C9 C 0.5717(3) 1.1096(2) 0.6316(2) 0.0236(5) Uani 1 1 d . . .
H9 H 0.6208 1.1239 0.5541 0.028 Uiso 1 1 calc R . .
C10 C 0.5245(3) 0.9901(2) 0.6774(2) 0.0212(5) Uani 1 1 d . . .
C11 C 0.5527(3) 0.8910(2) 0.6085(2) 0.0244(5) Uani 1 1 d . . .
H11 H 0.6015 0.9043 0.5308 0.029 Uiso 1 1 calc R . .
C12 C 0.5097(3) 0.7763(2) 0.6537(2) 0.0250(6) Uani 1 1 d . . .
H12 H 0.5291 0.7131 0.6063 0.030 Uiso 1 1 calc R . .
C13 C 0.4358(3) 0.7521(2) 0.7720(2) 0.0203(5) Uani 1 1 d . . .
C14 C 0.3954(3) 0.6337(2) 0.8195(2) 0.0240(6) Uani 1 1 d . . .
H14 H 0.4152 0.5698 0.7728 0.029 Uiso 1 1 calc R . .
C15 C 0.3268(3) 0.6118(2) 0.9347(2) 0.0239(5) Uani 1 1 d . . .
H15 H 0.3012 0.5332 0.9653 0.029 Uiso 1 1 calc R . .
C16 C 0.2957(3) 0.7069(2) 1.0055(2) 0.0210(5) Uani 1 1 d . . .
H16 H 0.2497 0.6905 1.0831 0.025 Uiso 1 1 calc R . .
C17 C 0.3321(3) 0.8265(2) 0.9627(2) 0.0179(5) Uani 1 1 d . . .
C18 C 0.3034(3) 0.9266(2) 1.0354(2) 0.0175(5) Uani 1 1 d . . .
C19 C 0.3494(3) 1.0446(2) 0.9858(2) 0.0165(5) Uani 1 1 d . . .
C20 C 0.4221(3) 1.0659(2) 0.8669(2) 0.0168(5) Uani 1 1 d . . .
C21 C 0.4487(3) 0.9684(2) 0.7962(2) 0.0170(5) Uani 1 1 d . . .
C22 C 0.4037(3) 0.8496(2) 0.8440(2) 0.0183(5) Uani 1 1 d . . .
C23 C -0.1277(7) 0.9423(8) 1.2601(6) 0.0238(14) Uani 0.50 1 d P A -1
H23 H -0.1567 0.8667 1.2975 0.029 Uiso 0.50 1 calc PR A -1
C24 C -0.1442(6) 1.0450(7) 1.3226(6) 0.0252(14) Uani 0.50 1 d P A -1
H24 H -0.1838 1.0368 1.4011 0.030 Uiso 0.50 1 calc PR A -1
C25 C -0.1021(10) 1.1570(9) 1.2682(8) 0.023(2) Uani 0.50 1 d P A -1
H25 H -0.1137 1.2238 1.3107 0.027 Uiso 0.50 1 calc PR A -1
C26 C -0.0421(6) 1.1731(6) 1.1504(5) 0.0176(12) Uani 0.50 1 d P A -1
C27 C 0.0041(8) 1.2884(8) 1.0924(6) 0.0192(16) Uani 0.50 1 d P A -1
H27 H -0.0094 1.3562 1.1340 0.023 Uiso 0.50 1 calc PR A -1
C28 C 0.0666(6) 1.3017(6) 0.9794(5) 0.0248(12) Uani 0.50 1 d P A -1
H28 H 0.0986 1.3779 0.9445 0.030 Uiso 0.50 1 calc PR A -1
C29 C 0.0852(8) 1.1999(8) 0.9108(6) 0.0169(14) Uani 0.50 1 d P A -1
C30 C 0.1475(6) 1.2137(5) 0.7924(5) 0.0263(12) Uani 0.50 1 d P A -1
H30 H 0.1767 1.2901 0.7569 0.032 Uiso 0.50 1 calc PR A -1
C31 C 0.1658(7) 1.1162(7) 0.7286(6) 0.0273(15) Uani 0.50 1 d P A -1
H31 H 0.2065 1.1269 0.6502 0.033 Uiso 0.50 1 calc PR A -1
C32 C 0.1230(6) 0.9982(6) 0.7816(5) 0.0192(12) Uani 0.50 1 d P A -1
C33 C 0.1372(10) 0.8949(10) 0.7179(8) 0.025(2) Uani 0.50 1 d P A -1
H33 H 0.1763 0.9047 0.6394 0.030 Uiso 0.50 1 calc PR A -1
C34 C 0.0955(7) 0.7834(7) 0.7682(6) 0.0245(16) Uani 0.50 1 d P A -1
H34 H 0.1082 0.7179 0.7239 0.029 Uiso 0.50 1 calc PR A -1
C35 C 0.0326(7) 0.7647(9) 0.8873(6) 0.0176(15) Uani 0.50 1 d P A -1
C36 C -0.0121(6) 0.6506(6) 0.9416(6) 0.0240(13) Uani 0.50 1 d P A -1
H36 H -0.0036 0.5847 0.8984 0.029 Uiso 0.50 1 calc PR A -1
C37 C -0.0691(6) 0.6331(6) 1.0590(6) 0.0284(12) Uani 0.50 1 d P A -1
H37 H -0.0959 0.5560 1.0936 0.034 Uiso 0.50 1 calc PR A -1
C38 C -0.0860(6) 0.7321(7) 1.1246(5) 0.0243(12) Uani 0.50 1 d P A -1
H38 H -0.1235 0.7205 1.2030 0.029 Uiso 0.50 1 calc PR A -1
C39 C -0.0467(7) 0.8484(9) 1.0732(6) 0.0170(14) Uani 0.50 1 d P A -1
C40 C -0.0675(5) 0.9541(6) 1.1415(5) 0.0165(11) Uani 0.50 1 d P A -1
C41 C -0.0243(7) 1.0696(8) 1.0855(6) 0.0132(13) Uani 0.50 1 d P A -1
C42 C 0.0418(5) 1.0852(6) 0.9666(5) 0.0156(10) Uani 0.50 1 d P A -1
C43 C 0.0592(7) 0.9822(8) 0.8998(6) 0.0152(14) Uani 0.50 1 d P A -1
C44 C 0.0158(5) 0.8654(6) 0.9554(5) 0.0160(10) Uani 0.50 1 d P A -1
O1 O 0.6584(2) 0.49531(18) 0.40191(17) 0.0324(4) Uani 1 1 d . . .
O2 O 0.7251(2) 0.51634(16) 0.82123(15) 0.0273(4) Uani 1 1 d . . .
O3 O 1.0108(2) 0.86020(16) 0.46334(15) 0.0299(4) Uani 1 1 d . . .
O4 O 0.83144(19) 0.32857(15) 0.47688(14) 0.0213(4) Uani 1 1 d . . .
O5 O 0.71023(19) 0.50267(16) 0.60856(14) 0.0228(4) Uani 1 1 d . . .
O6 O 0.8400(2) 0.66598(15) 0.44240(15) 0.0254(4) Uani 1 1 d . . .
O7 O 0.9645(2) 0.48929(15) 0.30581(14) 0.0221(4) Uani 1 1 d . . .
O8 O 0.87957(19) 0.67530(15) 0.63395(14) 0.0209(4) Uani 1 1 d . . .
O9 O 1.1279(2) 0.66157(15) 0.32994(14) 0.0227(4) Uani 1 1 d . . .
O10 O 1.0000 0.5000 0.5000 0.0155(5) Uani 1 2 d S . .
Mo1 Mo 0.80314(2) 0.498489(19) 0.441123(18) 0.02084(6) Uani 1 1 d . . .
Mo2 Mo 0.83753(2) 0.509705(18) 0.684801(17) 0.01819(6) Uani 1 1 d . . .
Mo3 Mo 1.00825(2) 0.708917(18) 0.477950(17) 0.01878(6) 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 1.392(3) . ?
C1 C18 1.412(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.411(3) . ?
C4 C19 1.427(3) . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(3) . ?
C6 H6 0.9300 . ?
C7 C20 1.425(3) . ?
C7 C8 1.428(3) . ?
C8 C9 1.359(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.425(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.416(3) . ?
C10 C21 1.425(3) . ?
C11 C12 1.366(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.421(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.407(4) . ?
C13 C22 1.423(3) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.400(3) . ?
C16 H16 0.9300 . ?
C17 C22 1.422(3) . ?
C17 C18 1.454(3) . ?
C18 C19 1.418(3) . ?
C19 C20 1.422(3) . ?
C20 C21 1.417(3) . ?
C21 C22 1.420(3) . ?
C23 C40 1.406(9) . ?
C23 C24 1.409(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.398(12) . ?
C25 H25 0.9300 . ?
C26 C27 1.426(9) . ?
C26 C41 1.433(9) . ?
C27 C28 1.342(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.446(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.404(9) . ?
C29 C42 1.406(9) . ?
C30 C31 1.370(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.427(9) . ?
C31 H31 0.9300 . ?
C32 C43 1.404(10) . ?
C32 C33 1.427(10) . ?
C33 C34 1.351(12) . ?
C33 H33 0.9300 . ?
C34 C35 1.416(10) . ?
C34 H34 0.9300 . ?
C35 C36 1.396(10) . ?
C35 C44 1.434(9) . ?
C36 C37 1.395(10) . ?
C36 H36 0.9300 . ?
C37 C38 1.399(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.400(9) . ?
C38 H38 0.9300 . ?
C39 C44 1.398(10) . ?
C39 C40 1.478(9) . ?
C40 C41 1.415(9) . ?
C41 C42 1.413(9) . ?
C42 C43 1.444(9) . ?
C43 C44 1.426(9) . ?
O1 Mo1 1.6824(19) . ?
O2 Mo2 1.6856(17) . ?
O3 Mo3 1.6764(17) . ?
O4 Mo3 1.9073(18) 2_766 ?
O4 Mo1 1.9513(17) . ?
O5 Mo2 1.8638(17) . ?
O5 Mo1 1.9938(17) . ?
O6 Mo1 1.9022(17) . ?
O6 Mo3 1.9506(18) . ?
O7 Mo1 1.8652(17) . ?
O7 Mo2 1.9976(18) 2_766 ?
O8 Mo2 1.9058(17) . ?
O8 Mo3 1.9344(17) . ?
O9 Mo3 1.9211(17) . ?
O9 Mo2 1.9354(17) 2_766 ?
O10 Mo2 2.3123(3) 2_766 ?
O10 Mo2 2.3123(3) . ?
O10 Mo3 2.3159(3) 2_766 ?
O10 Mo3 2.3159(3) . ?
O10 Mo1 2.3318(3) 2_766 ?
O10 Mo1 2.3318(3) . ?
Mo2 O9 1.9354(17) 2_766 ?
Mo2 O7 1.9976(18) 2_766 ?
Mo3 O4 1.9073(18) 2_766 ?

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 120.9(2) . . ?
C2 C1 H1 119.5 . . ?
C18 C1 H1 119.5 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 C19 119.1(2) . . ?
C5 C4 C19 119.3(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C20 119.1(2) . . ?
C6 C7 C8 121.6(2) . . ?
C20 C7 C8 119.4(2) . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 C21 118.7(2) . . ?
C9 C10 C21 119.4(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 C22 119.5(2) . . ?
C12 C13 C22 119.2(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 121.6(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C22 118.3(2) . . ?
C16 C17 C18 122.4(2) . . ?
C22 C17 C18 119.3(2) . . ?
C1 C18 C19 118.5(2) . . ?
C1 C18 C17 122.5(2) . . ?
C19 C18 C17 119.0(2) . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 C4 119.9(2) . . ?
C20 C19 C4 119.0(2) . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 C7 119.8(2) . . ?
C19 C20 C7 120.3(2) . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 C10 119.6(2) . . ?
C22 C21 C10 120.4(2) . . ?
C21 C22 C17 120.8(2) . . ?
C21 C22 C13 119.3(2) . . ?
C17 C22 C13 119.9(2) . . ?
C40 C23 C24 120.1(8) . . ?
C40 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.3(7) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 121.6(7) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C27 122.4(7) . . ?
C25 C26 C41 118.8(7) . . ?
C27 C26 C41 118.8(6) . . ?
C28 C27 C26 121.6(7) . . ?
C28 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C27 C28 C29 121.3(7) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C30 C29 C42 120.7(7) . . ?
C30 C29 C28 121.5(8) . . ?
C42 C29 C28 117.8(6) . . ?
C31 C30 C29 120.8(6) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 120.4(6) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C43 C32 C31 119.8(6) . . ?
C43 C32 C33 118.2(8) . . ?
C31 C32 C33 121.9(7) . . ?
C34 C33 C32 121.9(8) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 120.9(7) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C36 C35 C34 122.2(7) . . ?
C36 C35 C44 118.4(7) . . ?
C34 C35 C44 119.4(8) . . ?
C37 C36 C35 121.4(6) . . ?
C37 C36 H36 119.3 . . ?
C35 C36 H36 119.3 . . ?
C36 C37 C38 119.7(6) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C37 C38 C39 120.4(6) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C44 C39 C38 119.9(7) . . ?
C44 C39 C40 119.1(8) . . ?
C38 C39 C40 121.0(6) . . ?
C23 C40 C41 119.5(6) . . ?
C23 C40 C39 121.6(7) . . ?
C41 C40 C39 118.8(6) . . ?
C42 C41 C40 121.5(6) . . ?
C42 C41 C26 118.8(8) . . ?
C40 C41 C26 119.6(6) . . ?
C29 C42 C41 121.6(6) . . ?
C29 C42 C43 118.8(6) . . ?
C41 C42 C43 119.6(6) . . ?
C32 C43 C44 121.2(6) . . ?
C32 C43 C42 119.5(8) . . ?
C44 C43 C42 119.3(6) . . ?
C39 C44 C43 121.6(6) . . ?
C39 C44 C35 120.1(7) . . ?
C43 C44 C35 118.3(6) . . ?
Mo3 O4 Mo1 116.99(8) 2_766 . ?
Mo2 O5 Mo1 116.38(9) . . ?
Mo1 O6 Mo3 116.88(9) . . ?
Mo1 O7 Mo2 116.70(8) . 2_766 ?
Mo2 O8 Mo3 116.79(8) . . ?
Mo3 O9 Mo2 116.24(8) . 2_766 ?
Mo2 O10 Mo2 179.999(1) 2_766 . ?
Mo2 O10 Mo3 89.928(7) 2_766 2_766 ?
Mo2 O10 Mo3 90.073(7) . 2_766 ?
Mo2 O10 Mo3 90.072(7) 2_766 . ?
Mo2 O10 Mo3 89.927(7) . . ?
Mo3 O10 Mo3 179.999(1) 2_766 . ?
Mo2 O10 Mo1 89.822(10) 2_766 2_766 ?
Mo2 O10 Mo1 90.177(10) . 2_766 ?
Mo3 O10 Mo1 89.879(8) 2_766 2_766 ?
Mo3 O10 Mo1 90.122(8) . 2_766 ?
Mo2 O10 Mo1 90.178(10) 2_766 . ?
Mo2 O10 Mo1 89.823(10) . . ?
Mo3 O10 Mo1 90.121(8) 2_766 . ?
Mo3 O10 Mo1 89.879(8) . . ?
Mo1 O10 Mo1 180.000(11) 2_766 . ?
O1 Mo1 O7 103.74(9) . . ?
O1 Mo1 O6 104.01(9) . . ?
O7 Mo1 O6 90.70(8) . . ?
O1 Mo1 O4 103.31(9) . . ?
O7 Mo1 O4 88.36(7) . . ?
O6 Mo1 O4 152.08(7) . . ?
O1 Mo1 O5 103.26(9) . . ?
O7 Mo1 O5 152.89(7) . . ?
O6 Mo1 O5 85.11(8) . . ?
O4 Mo1 O5 83.15(7) . . ?
O1 Mo1 O10 178.46(7) . . ?
O7 Mo1 O10 77.53(5) . . ?
O6 Mo1 O10 76.76(5) . . ?
O4 Mo1 O10 75.79(5) . . ?
O5 Mo1 O10 75.44(5) . . ?
O2 Mo2 O5 104.05(9) . . ?
O2 Mo2 O8 103.19(8) . . ?
O5 Mo2 O8 90.39(8) . . ?
O2 Mo2 O9 103.04(8) . 2_766 ?
O5 Mo2 O9 89.44(8) . 2_766 ?
O8 Mo2 O9 152.99(7) . 2_766 ?
O2 Mo2 O7 102.04(8) . 2_766 ?
O5 Mo2 O7 153.89(7) . 2_766 ?
O8 Mo2 O7 84.61(7) . 2_766 ?
O9 Mo2 O7 83.75(7) 2_766 2_766 ?
O2 Mo2 O10 177.62(7) . . ?
O5 Mo2 O10 78.31(5) . . ?
O8 Mo2 O10 76.91(5) . . ?
O9 Mo2 O10 76.61(5) 2_766 . ?
O7 Mo2 O10 75.59(5) 2_766 . ?
O3 Mo3 O4 103.75(9) . 2_766 ?
O3 Mo3 O9 103.97(8) . . ?
O4 Mo3 O9 88.20(8) 2_766 . ?
O3 Mo3 O8 102.92(8) . . ?
O4 Mo3 O8 87.52(7) 2_766 . ?
O9 Mo3 O8 153.02(7) . . ?
O3 Mo3 O6 102.98(9) . . ?
O4 Mo3 O6 153.25(7) 2_766 . ?
O9 Mo3 O6 86.42(8) . . ?
O8 Mo3 O6 85.52(8) . . ?
O3 Mo3 O10 178.93(7) . . ?
O4 Mo3 O10 76.99(5) 2_766 . ?
O9 Mo3 O10 76.78(5) . . ?
O8 Mo3 O10 76.30(5) . . ?
O6 Mo3 O10 76.27(5) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.074
