#------------------------------------------------------------------------------
#$Date: 2019-07-17 10:10:01 +0300 (Wed, 17 Jul 2019) $
#$Revision: 217108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233176.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7233176
loop_
_publ_author_name
'Bilal R. Kaafarani'
'Ala'a O. El-Ballouli'
'Roman Trattnig'
'Alexandr Fonari'
'Stefan Sax'
'Brigitte Wex'
'Chad Risko'
'Rony S. Khnayzer'
'Stephen Barlow'
'Digambara Patra'
'Tatiana V. Timofeeva'
'Emil J. W. List'
'Jean-Luc Bredase'
'Seth R. Mardere'
_publ_section_title
;
 Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis,
 structures, optical properties, electrochemistry, and electroluminescence
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1638
_journal_page_last               1650
_journal_paper_doi               10.1039/C2TC00474G
_journal_volume                  1
_journal_year                    2013
_chemical_formula_moiety         'C40 H28 N2'
_chemical_formula_sum            'C40 H28 N2'
_chemical_formula_weight         536.64
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 106.701(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.167(5)
_cell_length_b                   13.192(5)
_cell_length_c                   8.213(3)
_cell_measurement_reflns_used    1462
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.68
_cell_measurement_theta_min      2.23
_cell_volume                     1366.4(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.2418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                1548
_reflns_number_total             2398
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000003.cif
_cod_data_source_block           PCOD1000003
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1366.4(8)
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               7233176
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'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.75405(13) 0.21105(13) 0.3295(2) 0.0380(4) Uani 1 1 d . . .
C1 C 0.65185(17) 0.22067(16) 0.2177(3) 0.0397(5) Uani 1 1 d . . .
C2 C 0.60432(17) 0.30441(18) 0.1240(3) 0.0439(6) Uani 1 1 d . . .
H2A H 0.6405 0.3673 0.1317 0.053 Uiso 1 1 calc R . .
C3 C 0.50181(18) 0.2923(2) 0.0188(3) 0.0500(6) Uani 1 1 d . . .
H3A H 0.4676 0.3482 -0.0478 0.060 Uiso 1 1 calc R . .
C4 C 0.44786(19) 0.2016(2) 0.0077(3) 0.0545(7) Uani 1 1 d . . .
H4A H 0.3771 0.1966 -0.0636 0.065 Uiso 1 1 calc R . .
C5 C 0.49570(18) 0.1186(2) 0.0989(3) 0.0506(6) Uani 1 1 d . . .
H5A H 0.4585 0.0562 0.0901 0.061 Uiso 1 1 calc R . .
C6 C 0.59982(17) 0.12670(17) 0.2050(3) 0.0416(5) Uani 1 1 d . . .
C7 C 0.67297(16) 0.05780(16) 0.3143(3) 0.0403(5) Uani 1 1 d . . .
C8 C 0.66581(19) -0.04279(17) 0.3591(3) 0.0489(6) Uani 1 1 d . . .
H8A H 0.6029 -0.0805 0.3105 0.059 Uiso 1 1 calc R . .
C9 C 0.7513(2) -0.08720(17) 0.4750(3) 0.0507(6) Uani 1 1 d . . .
H9A H 0.7466 -0.1560 0.5064 0.061 Uiso 1 1 calc R . .
C10 C 0.84473(19) -0.03292(16) 0.5476(3) 0.0476(6) Uani 1 1 d . . .
H10A H 0.9024 -0.0655 0.6269 0.057 Uiso 1 1 calc R . .
C11 C 0.85428(18) 0.06721(15) 0.5055(3) 0.0413(5) Uani 1 1 d . . .
H11A H 0.9174 0.1044 0.5546 0.050 Uiso 1 1 calc R . .
C12 C 0.76754(17) 0.11156(15) 0.3882(3) 0.0376(5) Uani 1 1 d . . .
C13 C 0.82682(16) 0.29236(16) 0.3845(3) 0.0368(5) Uani 1 1 d . . .
C14 C 0.79354(17) 0.38060(16) 0.4441(3) 0.0436(6) Uani 1 1 d . . .
H14A H 0.7235 0.3847 0.4540 0.052 Uiso 1 1 calc R . .
C15 C 0.86070(17) 0.46298(15) 0.4896(3) 0.0410(5) Uani 1 1 d . . .
C16 C 0.96422(15) 0.45608(14) 0.4782(2) 0.0349(5) Uani 1 1 d . . .
C17 C 0.99898(17) 0.36605(16) 0.4226(3) 0.0511(6) Uani 1 1 d . . .
C18 C 0.92939(16) 0.28491(17) 0.3746(3) 0.0487(6) Uani 1 1 d . . .
H18A H 0.9526 0.2241 0.3346 0.058 Uiso 1 1 calc R . .
C19 C 0.8416(5) 0.5514(5) 0.5873(8) 0.0370(14) Uani 0.50 1 d P . 1
H19A H 0.8741 0.5388 0.7102 0.044 Uiso 0.50 1 calc PR . 1
H19B H 0.7643 0.5600 0.5678 0.044 Uiso 0.50 1 calc PR . 1
C20 C 1.1126(4) 0.3515(3) 0.4631(8) 0.0422(12) Uani 0.50 1 d P . 1
H20C H 1.1288 0.2931 0.3993 0.051 Uiso 0.50 1 calc PR . 1
H20D H 1.1432 0.3385 0.5862 0.051 Uiso 0.50 1 calc PR . 1
C19' C 0.8093(5) 0.5692(5) 0.5063(7) 0.0376(15) Uani 0.50 1 d P . 2
H19C H 0.7913 0.6060 0.3967 0.045 Uiso 0.50 1 calc PR . 2
H19D H 0.7440 0.5605 0.5416 0.045 Uiso 0.50 1 calc PR . 2
C20' C 1.1070(3) 0.3734(4) 0.3586(6) 0.0353(11) Uani 0.50 1 d P . 2
H20A H 1.1328 0.3046 0.3434 0.042 Uiso 0.50 1 calc PR . 2
H20B H 1.0911 0.4096 0.2485 0.042 Uiso 0.50 1 calc PR . 2
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'
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
C12 N1 C1 108.39(17) . .
C12 N1 C13 126.43(17) . .
C1 N1 C13 124.93(17) . .
C2 C1 N1 129.1(2) . .
C2 C1 C6 121.9(2) . .
N1 C1 C6 108.94(19) . .
C3 C2 C1 117.2(2) . .
C3 C2 H2A 121.4 . .
C1 C2 H2A 121.4 . .
C4 C3 C2 122.1(2) . .
C4 C3 H3A 119.0 . .
C2 C3 H3A 119.0 . .
C5 C4 C3 120.6(2) . .
C5 C4 H4A 119.7 . .
C3 C4 H4A 119.7 . .
C4 C5 C6 119.4(2) . .
C4 C5 H5A 120.3 . .
C6 C5 H5A 120.3 . .
C5 C6 C1 118.8(2) . .
C5 C6 C7 134.5(2) . .
C1 C6 C7 106.67(18) . .
C8 C7 C12 119.1(2) . .
C8 C7 C6 133.4(2) . .
C12 C7 C6 107.54(18) . .
C9 C8 C7 119.0(2) . .
C9 C8 H8A 120.5 . .
C7 C8 H8A 120.5 . .
C8 C9 C10 121.3(2) . .
C8 C9 H9A 119.4 . .
C10 C9 H9A 119.4 . .
C11 C10 C9 121.0(2) . .
C11 C10 H10A 119.5 . .
C9 C10 H10A 119.5 . .
C10 C11 C12 117.3(2) . .
C10 C11 H11A 121.3 . .
C12 C11 H11A 121.3 . .
N1 C12 C11 129.26(19) . .
N1 C12 C7 108.45(18) . .
C11 C12 C7 122.23(19) . .
C18 C13 C14 119.8(2) . .
C18 C13 N1 120.58(19) . .
C14 C13 N1 119.63(18) . .
C13 C14 C15 120.95(19) . .
C13 C14 H14A 119.5 . .
C15 C14 H14A 119.5 . .
C14 C15 C16 119.44(19) . .
C14 C15 C19 124.9(3) . .
C16 C15 C19 114.2(3) . .
C14 C15 C19' 117.6(3) . .
C16 C15 C19' 121.0(3) . .
C19 C15 C19' 26.9(2) . .
C17 C16 C15 119.72(19) . .
C17 C16 C16 120.2(2) . 3_766
C15 C16 C16 120.1(2) . 3_766
C18 C17 C16 119.8(2) . .
C18 C17 C20 121.1(3) . .
C16 C17 C20 116.8(3) . .
C18 C17 C20' 120.7(3) . .
C16 C17 C20' 116.5(2) . .
C20 C17 C20' 32.4(2) . .
C13 C18 C17 120.3(2) . .
C13 C18 H18A 119.8 . .
C17 C18 H18A 119.8 . .
C15 C19 C20 111.9(4) . 3_766
C15 C19 H19A 109.2 . .
C20 C19 H19A 109.2 3_766 .
C15 C19 H19B 109.2 . .
C20 C19 H19B 109.2 3_766 .
H19A C19 H19B 107.9 . .
C17 C20 C19 106.9(4) . 3_766
C17 C20 H20C 110.3 . .
C19 C20 H20C 110.3 3_766 .
C17 C20 H20D 110.3 . .
C19 C20 H20D 110.3 3_766 .
H20C C20 H20D 108.6 . .
C20' C19' C15 105.4(4) 3_766 .
C20' C19' H19C 110.7 3_766 .
C15 C19' H19C 110.7 . .
C20' C19' H19D 110.7 3_766 .
C15 C19' H19D 110.7 . .
H19C C19' H19D 108.8 . .
C19' C20' C17 107.8(4) 3_766 .
C19' C20' H20A 110.1 3_766 .
C17 C20' H20A 110.1 . .
C19' C20' H20B 110.1 3_766 .
C17 C20' H20B 110.1 . .
H20A C20' H20B 108.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C12 1.392(3) .
N1 C1 1.400(3) .
N1 C13 1.423(3) .
C1 C2 1.388(3) .
C1 C6 1.406(3) .
C2 C3 1.387(3) .
C2 H2A 0.9500 .
C3 C4 1.381(3) .
C3 H3A 0.9500 .
C4 C5 1.374(3) .
C4 H4A 0.9500 .
C5 C6 1.401(3) .
C5 H5A 0.9500 .
C6 C7 1.436(3) .
C7 C8 1.387(3) .
C7 C12 1.410(3) .
C8 C9 1.378(3) .
C8 H8A 0.9500 .
C9 C10 1.400(3) .
C9 H9A 0.9500 .
C10 C11 1.380(3) .
C10 H10A 0.9500 .
C11 C12 1.394(3) .
C11 H11A 0.9500 .
C13 C18 1.380(3) .
C13 C14 1.382(3) .
C14 C15 1.383(3) .
C14 H14A 0.9500 .
C15 C16 1.396(3) .
C15 C19 1.478(7) .
C15 C19' 1.579(6) .
C16 C17 1.396(3) .
C16 C16 1.471(4) 3_766
C17 C18 1.390(3) .
C17 C20 1.448(5) .
C17 C20' 1.655(5) .
C18 H18A 0.9500 .
C19 C20 1.523(8) 3_766
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C19 1.523(8) 3_766
C20 H20C 0.9900 .
C20 H20D 0.9900 .
C19' C20' 1.522(8) 3_766
C19' H19C 0.9900 .
C19' H19D 0.9900 .
C20' C19' 1.522(8) 3_766
C20' H20A 0.9900 .
C20' H20B 0.9900 .
