#------------------------------------------------------------------------------
#$Date: 2019-10-02 12:00:18 +0300 (Wed, 02 Oct 2019) $
#$Revision: 219018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234304.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_7234304
loop_
_publ_author_name
'Tien-Lin Wu'
'Chi-Hsien Kuo'
'Bo-Chao Lin'
'Yu-Tai Tao'
'Chao-Ping Hsu'
'Rai-Shung Liu'
_publ_section_title
;
 Synthesis of planar dibenzo[de,op]bistetracene derivatives for organic
 field-effect transistor applications: substituent effect on crystal
 packing and charge transport property
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              7583
_journal_page_last               7588
_journal_paper_doi               10.1039/C5TC01455G
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C42 H32'
_chemical_formula_sum            'C42 H32'
_chemical_formula_weight         536.68
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/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                 119.161(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.659(4)
_cell_length_b                   6.1038(11)
_cell_length_c                   19.317(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2744.9(9)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1070
_diffrn_reflns_av_sigmaI/netI    0.1454
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8616
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9993
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange-red
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.2130
_refine_ls_R_factor_gt           0.0680
_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)+(0.1188P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.2590
_reflns_number_gt                902
_reflns_number_total             2427
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2015-3-7583.cif
_cod_data_source_block           ch15723
_cod_original_cell_volume        2745.0(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7234304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.0602(2) 0.4832(8) 0.1649(3) 0.0405(14) Uani 1 1 d . . .
C2 C 0.0828(3) 0.5435(15) 0.1090(3) 0.125(4) Uani 1 1 d . . .
H2A H 0.1174 0.4575 0.1223 0.188 Uiso 1 1 calc R . .
H2B H 0.0923 0.6999 0.1143 0.188 Uiso 1 1 calc R . .
H2C H 0.0534 0.5122 0.0543 0.188 Uiso 1 1 calc R . .
C3 C 0.0075(3) 0.6121(11) 0.1447(3) 0.091(3) Uani 1 1 d . . .
H3A H -0.0215 0.5824 0.0896 0.137 Uiso 1 1 calc R . .
H3B H 0.0169 0.7686 0.1509 0.137 Uiso 1 1 calc R . .
H3C H -0.0075 0.5702 0.1801 0.137 Uiso 1 1 calc R . .
C4 C 0.0440(3) 0.2439(10) 0.1502(3) 0.108(3) Uani 1 1 d . . .
H4A H 0.0783 0.1566 0.1629 0.161 Uiso 1 1 calc R . .
H4B H 0.0155 0.2226 0.0943 0.161 Uiso 1 1 calc R . .
H4C H 0.0278 0.1973 0.1837 0.161 Uiso 1 1 calc R . .
C5 C 0.10524(19) 0.5313(8) 0.2517(3) 0.0366(14) Uani 1 1 d . . .
C6 C 0.1106(2) 0.3972(8) 0.3132(3) 0.0374(14) Uani 1 1 d . . .
H6 H 0.0859 0.2741 0.3007 0.045 Uiso 1 1 calc R . .
C7 C 0.1506(2) 0.4358(8) 0.3923(3) 0.0321(13) Uani 1 1 d . . .
C8 C 0.18821(19) 0.6169(7) 0.4103(3) 0.0283(12) Uani 1 1 d . . .
C9 C 0.18292(19) 0.7584(8) 0.3489(3) 0.0305(13) Uani 1 1 d . . .
C10 C 0.1412(2) 0.7096(8) 0.2699(3) 0.0377(14) Uani 1 1 d . . .
H10 H 0.1379 0.8021 0.2283 0.045 Uiso 1 1 calc R . .
C11 C 0.23151(19) 0.6600(7) 0.4915(3) 0.0284(12) Uani 1 1 d . . .
C12 C 0.23641(19) 0.5180(7) 0.5539(3) 0.0282(12) Uani 1 1 d . . .
C13 C 0.19921(19) 0.3318(7) 0.5345(2) 0.0276(12) Uani 1 1 d . . .
C14 C 0.1563(2) 0.2882(7) 0.4555(3) 0.0304(12) Uani 1 1 d . . .
C15 C 0.1214(2) 0.1053(8) 0.4413(3) 0.0396(14) Uani 1 1 d . . .
H15 H 0.0921 0.0764 0.3886 0.047 Uiso 1 1 calc R . .
C16 C 0.1280(2) -0.0365(8) 0.5014(3) 0.0411(14) Uani 1 1 d . . .
H16 H 0.1034 -0.1599 0.4895 0.049 Uiso 1 1 calc R . .
C17 C 0.1698(2) 0.0021(8) 0.5775(3) 0.0411(14) Uani 1 1 d . . .
H17 H 0.1747 -0.0968 0.6183 0.049 Uiso 1 1 calc R . .
C18 C 0.2058(2) 0.1874(7) 0.5962(3) 0.0325(13) Uani 1 1 d . . .
C19 C 0.2496(2) 0.2293(9) 0.6749(3) 0.0374(14) Uani 1 1 d . . .
H19 H 0.2544 0.1331 0.7163 0.045 Uiso 1 1 calc R . .
C20 C 0.2843(2) 0.4039(8) 0.6914(3) 0.0333(13) Uani 1 1 d . . .
H20 H 0.3135 0.4269 0.7446 0.040 Uiso 1 1 calc R . .
C21 C 0.2791(2) 0.5559(8) 0.6321(3) 0.0313(12) Uani 1 1 d . . .
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'
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
C3 C1 C4 108.4(5) . .
C3 C1 C2 109.7(5) . .
C4 C1 C2 106.0(6) . .
C3 C1 C5 108.7(4) . .
C4 C1 C5 112.9(4) . .
C2 C1 C5 111.0(5) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C10 C5 C6 118.5(4) . .
C10 C5 C1 120.3(5) . .
C6 C5 C1 121.2(5) . .
C7 C6 C5 122.8(5) . .
C7 C6 H6 118.6 . .
C5 C6 H6 118.6 . .
C6 C7 C8 118.3(5) . .
C6 C7 C14 121.5(4) . .
C8 C7 C14 120.1(4) . .
C7 C8 C9 119.9(4) . .
C7 C8 C11 120.2(4) . .
C9 C8 C11 119.8(4) . .
C10 C9 C8 118.7(4) . .
C10 C9 C21 121.7(5) . 7_566
C8 C9 C21 119.6(4) . 7_566
C5 C10 C9 121.7(5) . .
C5 C10 H10 119.2 . .
C9 C10 H10 119.2 . .
C11 C11 C12 120.6(5) 7_566 .
C11 C11 C8 119.6(5) 7_566 .
C12 C11 C8 119.8(4) . .
C21 C12 C13 120.6(4) . .
C21 C12 C11 120.0(4) . .
C13 C12 C11 119.3(4) . .
C14 C13 C18 119.4(4) . .
C14 C13 C12 121.6(4) . .
C18 C13 C12 119.0(4) . .
C15 C14 C13 118.3(5) . .
C15 C14 C7 122.8(4) . .
C13 C14 C7 118.9(4) . .
C16 C15 C14 122.3(5) . .
C16 C15 H15 118.8 . .
C14 C15 H15 118.8 . .
C17 C16 C15 119.8(5) . .
C17 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
C16 C17 C18 120.7(5) . .
C16 C17 H17 119.6 . .
C18 C17 H17 119.6 . .
C17 C18 C19 121.4(5) . .
C17 C18 C13 119.4(4) . .
C19 C18 C13 119.2(4) . .
C20 C19 C18 120.6(5) . .
C20 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C19 C20 C21 122.6(4) . .
C19 C20 H20 118.7 . .
C21 C20 H20 118.7 . .
C12 C21 C20 118.0(5) . .
C12 C21 C9 120.4(4) . 7_566
C20 C21 C9 121.6(4) . 7_566
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.485(7) .
C1 C4 1.510(7) .
C1 C2 1.517(8) .
C1 C5 1.541(6) .
C2 H2A 0.9800 .
C2 H2B 0.9800 .
C2 H2C 0.9800 .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C10 1.378(6) .
C5 C6 1.392(6) .
C6 C7 1.393(6) .
C6 H6 0.9500 .
C7 C8 1.416(6) .
C7 C14 1.465(6) .
C8 C9 1.418(6) .
C8 C11 1.448(6) .
C9 C10 1.415(6) .
C9 C21 1.443(6) 7_566
C10 H10 0.9500 .
C11 C11 1.404(8) 7_566
C11 C12 1.439(6) .
C12 C21 1.398(6) .
C12 C13 1.433(6) .
C13 C14 1.417(6) .
C13 C18 1.424(6) .
C14 C15 1.392(6) .
C15 C16 1.390(6) .
C15 H15 0.9500 .
C16 C17 1.365(6) .
C16 H16 0.9500 .
C17 C18 1.412(6) .
C17 H17 0.9500 .
C18 C19 1.417(6) .
C19 C20 1.345(6) .
C19 H19 0.9500 .
C20 C21 1.426(6) .
C20 H20 0.9500 .
C21 C9 1.443(6) 7_566
