#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/41/4034140.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_4034140
loop_
_publ_author_name
'Kumar, Sushil'
'Pola, Someshwar'
'Huang, Chih-Wei'
'Islam, Md Minarul'
'Venkateswarlu, Samala'
'Tao, Yu-Tai'
_publ_section_title
;
 Polysubstituted Hexa-cata-hexabenzocoronenes: Syntheses,
 Characterization, and Their Potential as Semiconducting Materials in
 Transistor Applications.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8562
_journal_page_last               8570
_journal_paper_doi               10.1021/acs.joc.9b00802
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C48 H20 Cl4'
_chemical_formula_sum            'C48 H20 Cl4'
_chemical_formula_weight         738.44
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.388(3)
_cell_angle_beta                 86.076(4)
_cell_angle_gamma                82.825(4)
_cell_formula_units_Z            1
_cell_length_a                   4.0737(6)
_cell_length_b                   14.151(2)
_cell_length_c                   14.771(2)
_cell_measurement_reflns_used    8602
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.102
_cell_measurement_theta_min      2.578
_cell_volume                     773.95(19)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18798
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.8226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0644
_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)+(0.1091P)²+0.7279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                2244
_reflns_number_total             2729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00802_si_002.cif
_cod_data_source_block           d21165
_cod_original_cell_volume        773.9(2)
_cod_database_code               4034140
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3208(9) 0.0606(3) 0.7916(2) 0.0313(8) Uani 1 1 d .
C2 C 0.3433(9) 0.0383(3) 0.7078(3) 0.0323(8) Uani 1 1 d .
H2 H 0.2912 -0.0267 0.7111 0.039 Uiso 1 1 calc R
C3 C 0.4421(8) 0.1119(2) 0.6202(2) 0.0287(7) Uani 1 1 d .
H3 H 0.4564 0.0970 0.5627 0.034 Uiso 1 1 calc R
C4 C 0.5239(8) 0.2097(2) 0.6119(2) 0.0257(7) Uani 1 1 d .
C5 C 0.4938(8) 0.2316(2) 0.6983(2) 0.0253(7) Uani 1 1 d .
C6 C 0.3883(8) 0.1542(2) 0.7878(2) 0.0299(7) Uani 1 1 d .
H6 H 0.3641 0.1678 0.8460 0.036 Uiso 1 1 calc R
C7 C 0.6022(8) 0.2906(2) 0.5182(2) 0.0246(7) Uani 1 1 d .
C8 C 0.7304(8) 0.2705(2) 0.4328(2) 0.0258(7) Uani 1 1 d .
C9 C 0.8990(8) 0.1735(3) 0.4415(2) 0.0285(7) Uani 1 1 d .
H9 H 0.9049 0.1173 0.5044 0.034 Uiso 1 1 calc R
C10 C 1.0531(8) 0.1576(3) 0.3630(3) 0.0312(8) Uani 1 1 d .
H10 H 1.1610 0.0913 0.3709 0.037 Uiso 1 1 calc R
C11 C 1.0491(8) 0.2404(3) 0.2710(2) 0.0295(7) Uani 1 1 d .
C12 C 0.8916(8) 0.3360(3) 0.2584(2) 0.0280(7) Uani 1 1 d .
H12 H 0.8946 0.3913 0.1950 0.034 Uiso 1 1 calc R
C13 C 0.7250(8) 0.3536(2) 0.3381(2) 0.0257(7) Uani 1 1 d .
C14 C 0.5794(8) 0.4562(2) 0.3274(2) 0.0251(7) Uani 1 1 d .
C15 C 0.5383(8) 0.4774(2) 0.4122(2) 0.0242(7) Uani 1 1 d .
C16 C 0.5532(8) 0.3935(2) 0.5091(2) 0.0246(7) Uani 1 1 d .
C17 C 0.4830(8) 0.5836(2) 0.4032(2) 0.0250(7) Uani 1 1 d .
C18 C 0.4649(8) 0.6649(2) 0.3096(2) 0.0259(7) Uani 1 1 d .
C19 C 0.4124(8) 0.6409(2) 0.2255(2) 0.0263(7) Uani 1 1 d .
C20 C 0.4740(8) 0.5369(2) 0.2337(2) 0.0254(7) Uani 1 1 d .
C21 C 0.3989(8) 0.5155(3) 0.1518(2) 0.0293(7) Uani 1 1 d .
H21 H 0.4393 0.4462 0.1561 0.035 Uiso 1 1 calc R
C22 C 0.2705(9) 0.5911(3) 0.0670(2) 0.0333(8) Uani 1 1 d .
H22 H 0.2285 0.5745 0.0129 0.040 Uiso 1 1 calc R
C23 C 0.2012(9) 0.6927(3) 0.0602(2) 0.0348(8) Uani 1 1 d .
H23 H 0.1073 0.7453 0.0019 0.042 Uiso 1 1 calc R
C24 C 0.2688(9) 0.7165(3) 0.1375(2) 0.0310(8) Uani 1 1 d .
H24 H 0.2179 0.7859 0.1322 0.037 Uiso 1 1 calc R
Cl1 Cl 0.1852(3) -0.03061(7) 0.90291(7) 0.0496(3) Uani 1 1 d .
Cl2 Cl 1.2641(2) 0.22453(7) 0.17099(6) 0.0373(3) 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'
Cl Cl 0.1484 0.1585 '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_3
C6 C1 C2 121.5(3) .
C6 C1 Cl1 119.1(3) .
C2 C1 Cl1 119.3(3) .
C3 C2 C1 118.6(3) .
C3 C2 H2 120.7 .
C1 C2 H2 120.7 .
C2 C3 C4 122.6(3) .
C2 C3 H3 118.7 .
C4 C3 H3 118.7 .
C3 C4 C5 117.9(3) .
C3 C4 C7 122.6(3) .
C5 C4 C7 119.2(3) .
C6 C5 C4 118.3(3) .
C6 C5 C18 121.9(3) 2_666
C4 C5 C18 119.5(3) 2_666
C1 C6 C5 121.1(3) .
C1 C6 H6 119.4 .
C5 C6 H6 119.4 .
C16 C7 C4 118.6(3) .
C16 C7 C8 118.1(3) .
C4 C7 C8 123.3(3) .
C9 C8 C13 117.8(3) .
C9 C8 C7 122.3(3) .
C13 C8 C7 119.4(3) .
C10 C9 C8 122.6(3) .
C10 C9 H9 118.7 .
C8 C9 H9 118.7 .
C9 C10 C11 118.8(3) .
C9 C10 H10 120.6 .
C11 C10 H10 120.6 .
C12 C11 C10 121.2(3) .
C12 C11 Cl2 118.9(3) .
C10 C11 Cl2 119.8(3) .
C11 C12 C13 121.0(3) .
C11 C12 H12 119.5 .
C13 C12 H12 119.5 .
C12 C13 C8 118.7(3) .
C12 C13 C14 121.4(3) .
C8 C13 C14 119.7(3) .
C15 C14 C20 118.7(3) .
C15 C14 C13 117.9(3) .
C20 C14 C13 123.4(3) .
C14 C15 C17 119.9(3) .
C14 C15 C16 120.2(3) .
C17 C15 C16 119.9(3) .
C7 C16 C15 120.1(3) .
C7 C16 C17 120.0(3) 2_666
C15 C16 C17 119.8(3) 2_666
C18 C17 C15 120.0(3) .
C18 C17 C16 119.7(3) 2_666
C15 C17 C16 120.3(3) 2_666
C17 C18 C19 118.2(3) .
C17 C18 C5 118.4(3) 2_666
C19 C18 C5 123.4(3) 2_666
C24 C19 C20 118.2(3) .
C24 C19 C18 121.9(3) .
C20 C19 C18 119.6(3) .
C19 C20 C21 117.9(3) .
C19 C20 C14 119.1(3) .
C21 C20 C14 122.7(3) .
C22 C21 C20 122.2(3) .
C22 C21 H21 118.9 .
C20 C21 H21 118.9 .
C21 C22 C23 119.8(3) .
C21 C22 H22 120.1 .
C23 C22 H22 120.1 .
C24 C23 C22 119.9(3) .
C24 C23 H23 120.1 .
C22 C23 H23 120.1 .
C23 C24 C19 122.0(3) .
C23 C24 H24 119.0 .
C19 C24 H24 119.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.365(5) .
C1 C2 1.389(5) .
C1 Cl1 1.740(3) .
C2 C3 1.369(5) .
C2 H2 0.9500 .
C3 C4 1.420(4) .
C3 H3 0.9500 .
C4 C5 1.424(4) .
C4 C7 1.445(4) .
C5 C6 1.418(4) .
C5 C18 1.452(4) 2_666
C6 H6 0.9500 .
C7 C16 1.398(4) .
C7 C8 1.450(4) .
C8 C9 1.417(5) .
C8 C13 1.421(4) .
C9 C10 1.365(5) .
C9 H9 0.9500 .
C10 C11 1.394(5) .
C10 H10 0.9500 .
C11 C12 1.369(5) .
C11 Cl2 1.743(3) .
C12 C13 1.412(5) .
C12 H12 0.9500 .
C13 C14 1.449(4) .
C14 C15 1.395(4) .
C14 C20 1.449(4) .
C15 C17 1.444(4) .
C15 C16 1.447(4) .
C16 C17 1.451(4) 2_666
C17 C18 1.400(4) .
C17 C16 1.451(4) 2_666
C18 C19 1.449(4) .
C18 C5 1.452(4) 2_666
C19 C24 1.417(5) .
C19 C20 1.418(4) .
C20 C21 1.421(4) .
C21 C22 1.364(5) .
C21 H21 0.9500 .
C22 C23 1.395(5) .
C22 H22 0.9500 .
C23 C24 1.367(5) .
C23 H23 0.9500 .
C24 H24 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328083
