#------------------------------------------------------------------------------
#$Date: 2019-11-04 12:10:04 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222696 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/41/4034138.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_4034138
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 H16 F8'
_chemical_formula_sum            'C48 H16 F8'
_chemical_formula_weight         744.61
_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_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.980(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.541(6)
_cell_length_b                   8.0612(19)
_cell_length_c                   14.582(3)
_cell_measurement_reflns_used    7050
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.455
_cell_measurement_theta_min      2.647
_cell_volume                     3027.4(12)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.1109
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33862
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.385
_refine_diff_density_min         -0.947
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.897
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.897
_refine_ls_R_factor_all          0.2089
_refine_ls_R_factor_gt           0.1676
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4476
_refine_ls_wR_factor_ref         0.4729
_reflns_number_gt                3681
_reflns_number_total             5329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00802_si_007.cif
_cod_data_source_block           d21043
_cod_original_cell_volume        3027.5(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034138
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
C1 C 0.5545(4) 0.0400(16) 0.9226(7) 0.030(3) Uani 1 1 d .
C2 C 0.5129(4) 0.0191(14) 0.8480(8) 0.029(3) Uani 1 1 d .
H2 H 0.4791 0.0447 0.8550 0.035 Uiso 1 1 calc R
C3 C 0.5192(4) -0.0392(13) 0.7619(7) 0.026(2) Uani 1 1 d .
C4 C 0.4781(4) -0.0436(13) 0.6792(7) 0.021(2) Uani 1 1 d .
C5 C 0.4225(4) -0.0770(14) 0.6812(7) 0.025(2) Uani 1 1 d .
C6 C 0.4114(4) -0.1510(14) 0.7617(8) 0.025(2) Uani 1 1 d .
H6 H 0.4377 -0.1682 0.8180 0.031 Uiso 1 1 calc R
C7 C 0.3602(4) -0.1977(13) 0.7545(8) 0.029(3) Uani 1 1 d .
C8 C 0.3213(4) -0.1793(14) 0.6751(8) 0.032(3) Uani 1 1 d .
H8 H 0.2870 -0.2160 0.6727 0.039 Uiso 1 1 calc R
C9 C 0.3338(4) -0.1051(15) 0.5982(8) 0.027(2) Uani 1 1 d .
C10 C 0.3843(4) -0.0426(13) 0.5995(7) 0.022(2) Uani 1 1 d .
C11 C 0.3967(4) 0.0307(14) 0.5176(7) 0.025(2) Uani 1 1 d .
C12 C 0.4471(4) 0.0175(14) 0.5091(7) 0.024(2) Uani 1 1 d .
C13 C 0.4883(4) -0.0250(13) 0.5899(7) 0.021(2) Uani 1 1 d .
C14 C 0.4582(4) 0.0438(13) 0.4184(8) 0.025(2) Uani 1 1 d .
C15 C 0.4204(4) 0.0951(14) 0.3413(7) 0.024(2) Uani 1 1 d .
C16 C 0.3728(4) 0.1705(14) 0.3623(8) 0.027(2) Uani 1 1 d .
C17 C 0.3604(4) 0.1345(14) 0.4476(7) 0.026(2) Uani 1 1 d .
C18 C 0.3178(4) 0.2071(15) 0.4715(9) 0.033(3) Uani 1 1 d .
H18 H 0.3086 0.1770 0.5283 0.040 Uiso 1 1 calc R
C19 C 0.2888(4) 0.3244(15) 0.4110(8) 0.032(3) Uani 1 1 d .
H19 H 0.2607 0.3797 0.4278 0.038 Uiso 1 1 calc R
C20 C 0.3012(4) 0.3600(16) 0.3256(9) 0.036(3) Uani 1 1 d .
H20 H 0.2802 0.4347 0.2823 0.043 Uiso 1 1 calc R
C21 C 0.3429(4) 0.2895(14) 0.3041(8) 0.026(2) Uani 1 1 d .
H21 H 0.3521 0.3215 0.2476 0.032 Uiso 1 1 calc R
C22 C 0.4285(4) 0.0705(14) 0.2494(8) 0.028(3) Uani 1 1 d .
C23 C 0.3878(4) 0.0447(14) 0.1668(7) 0.024(2) Uani 1 1 d .
C24 C 0.3959(4) -0.0086(15) 0.0814(8) 0.032(3) Uani 1 1 d .
H24 H 0.3678 -0.0227 0.0276 0.039 Uiso 1 1 calc R
C25 C 0.0519(5) 0.5444(16) 0.1238(8) 0.032(2) Uani 1 1 d .
C26 C 0.1042(4) 0.5066(15) 0.1709(8) 0.031(3) Uani 1 1 d .
H26 H 0.1321 0.5150 0.1408 0.037 Uiso 1 1 calc R
C27 C 0.1111(4) 0.4565(16) 0.2638(8) 0.033(3) Uani 1 1 d .
C28 C 0.0713(5) 0.4279(14) 0.3091(8) 0.030(3) Uani 1 1 d .
C29 C 0.0207(4) 0.4605(14) 0.2555(8) 0.026(2) Uani 1 1 d .
C30 C 0.0118(4) 0.5207(15) 0.1625(8) 0.030(3) Uani 1 1 d .
H30 H -0.0226 0.5443 0.1275 0.036 Uiso 1 1 calc R
C31 C -0.0232(4) 0.4547(15) 0.2994(8) 0.027(2) Uani 1 1 d .
C32 C -0.0128(4) 0.4750(14) 0.3992(7) 0.025(2) Uani 1 1 d .
C33 C 0.0401(4) 0.4552(15) 0.4536(7) 0.028(3) Uani 1 1 d .
C34 C 0.0794(4) 0.3983(14) 0.4111(8) 0.026(2) Uani 1 1 d .
C35 C 0.1257(4) 0.3323(15) 0.4700(7) 0.026(2) Uani 1 1 d .
C36 C 0.1556(4) 0.2099(14) 0.4373(8) 0.031(3) Uani 1 1 d .
H36 H 0.1464 0.1783 0.3727 0.038 Uiso 1 1 calc R
C37 C 0.1979(4) 0.1355(15) 0.4974(9) 0.035(3) Uani 1 1 d .
H37 H 0.2171 0.0535 0.4738 0.042 Uiso 1 1 calc R
C38 C 0.2121(4) 0.1795(16) 0.5908(9) 0.037(3) Uani 1 1 d .
H38 H 0.2423 0.1320 0.6307 0.044 Uiso 1 1 calc R
C39 C 0.1835(4) 0.2905(15) 0.6270(8) 0.031(3) Uani 1 1 d .
H39 H 0.1931 0.3139 0.6928 0.037 Uiso 1 1 calc R
C40 C 0.1391(4) 0.3737(15) 0.5687(8) 0.033(3) Uani 1 1 d .
C41 C 0.1043(4) 0.4700(13) 0.6080(8) 0.026(2) Uani 1 1 d .
C42 C 0.0528(4) 0.4839(15) 0.5556(8) 0.028(2) Uani 1 1 d .
C43 C 0.1186(4) 0.5466(15) 0.7001(8) 0.031(3) Uani 1 1 d .
C44 C 0.1668(5) 0.6051(16) 0.7445(9) 0.036(3) Uani 1 1 d .
C45 C 0.1790(4) 0.6772(16) 0.8309(8) 0.033(3) Uani 1 1 d .
H45 H 0.2132 0.7150 0.8583 0.040 Uiso 1 1 calc R
C46 C 0.1403(5) 0.6934(15) 0.8770(7) 0.032(2) Uani 1 1 d .
C47 C 0.0900(4) 0.6555(14) 0.8364(8) 0.030(3) Uani 1 1 d .
H47 H 0.0636 0.6834 0.8676 0.036 Uiso 1 1 calc R
C48 C 0.0769(4) 0.5752(14) 0.7482(7) 0.026(2) Uani 1 1 d .
F1 F 0.5476(3) 0.1039(10) 1.0054(5) 0.0430(19) Uani 1 1 d .
F2 F 0.3490(3) -0.2682(10) 0.8326(5) 0.0459(19) Uani 1 1 d .
F3 F 0.2971(2) -0.1101(9) 0.5159(5) 0.0372(17) Uani 1 1 d .
F4 F 0.3380(2) 0.0567(9) 0.1721(5) 0.0372(17) Uani 1 1 d .
F5 F 0.0436(3) 0.6065(10) 0.0341(5) 0.0431(19) Uani 1 1 d .
F6 F 0.1616(2) 0.4399(8) 0.3122(5) 0.0357(17) Uani 1 1 d .
F7 F 0.2044(3) 0.6041(10) 0.6956(5) 0.0427(18) Uani 1 1 d .
F8 F 0.1523(3) 0.7696(10) 0.9620(5) 0.0449(19) 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'
F F 0.0171 0.0103 '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
C24 C1 F1 116.6(9) 3_656 .
C24 C1 C2 123.5(10) 3_656 .
F1 C1 C2 119.8(10) . .
C1 C2 C3 120.9(11) . .
C1 C2 H2 119.6 . .
C3 C2 H2 119.6 . .
C2 C3 C4 122.7(10) . .
C2 C3 C22 119.2(10) . 3_656
C4 C3 C22 117.2(9) . 3_656
C13 C4 C3 120.4(9) . .
C13 C4 C5 116.6(9) . .
C3 C4 C5 123.0(9) . .
C10 C5 C6 122.8(10) . .
C10 C5 C4 117.4(9) . .
C6 C5 C4 119.6(9) . .
C7 C6 C5 116.7(10) . .
C7 C6 H6 121.7 . .
C5 C6 H6 121.7 . .
C8 C7 F2 118.8(10) . .
C8 C7 C6 124.2(10) . .
F2 C7 C6 117.0(9) . .
C7 C8 C9 117.2(10) . .
C7 C8 H8 121.4 . .
C9 C8 H8 121.4 . .
F3 C9 C8 116.5(9) . .
F3 C9 C10 119.7(9) . .
C8 C9 C10 123.4(10) . .
C5 C10 C9 115.3(10) . .
C5 C10 C11 121.9(9) . .
C9 C10 C11 122.3(10) . .
C12 C11 C10 117.6(9) . .
C12 C11 C17 117.7(10) . .
C10 C11 C17 124.3(9) . .
C11 C12 C14 119.4(9) . .
C11 C12 C13 120.4(10) . .
C14 C12 C13 120.2(9) . .
C4 C13 C12 120.4(9) . .
C4 C13 C14 118.4(9) . 3_656
C12 C13 C14 121.1(10) . 3_656
C15 C14 C12 121.6(10) . .
C15 C14 C13 119.6(9) . 3_656
C12 C14 C13 118.7(10) . 3_656
C14 C15 C22 118.8(10) . .
C14 C15 C16 116.0(10) . .
C22 C15 C16 125.2(9) . .
C17 C16 C21 117.7(10) . .
C17 C16 C15 119.4(10) . .
C21 C16 C15 122.6(10) . .
C18 C17 C16 121.2(10) . .
C18 C17 C11 119.8(10) . .
C16 C17 C11 118.6(9) . .
C17 C18 C19 119.1(11) . .
C17 C18 H18 120.5 . .
C19 C18 H18 120.5 . .
C20 C19 C18 119.5(11) . .
C20 C19 H19 120.3 . .
C18 C19 H19 120.3 . .
C21 C20 C19 120.5(11) . .
C21 C20 H20 119.8 . .
C19 C20 H20 119.8 . .
C20 C21 C16 121.8(11) . .
C20 C21 H21 119.1 . .
C16 C21 H21 119.1 . .
C23 C22 C15 124.1(9) . .
C23 C22 C3 115.2(10) . 3_656
C15 C22 C3 119.8(9) . 3_656
F4 C23 C24 116.3(9) . .
F4 C23 C22 119.7(9) . .
C24 C23 C22 123.7(10) . .
C1 C24 C23 117.5(10) 3_656 .
C1 C24 H24 121.3 3_656 .
C23 C24 H24 121.3 . .
C30 C25 F5 119.7(10) . .
C30 C25 C26 123.4(10) . .
F5 C25 C26 116.9(10) . .
C27 C26 C25 114.6(10) . .
C27 C26 H26 122.7 . .
C25 C26 H26 122.7 . .
F6 C27 C26 114.6(10) . .
F6 C27 C28 120.2(10) . .
C26 C27 C28 125.2(11) . .
C27 C28 C29 115.9(10) . .
C27 C28 C34 124.2(11) . .
C29 C28 C34 118.8(10) . .
C30 C29 C28 121.2(10) . .
C30 C29 C31 117.8(10) . .
C28 C29 C31 120.4(10) . .
C25 C30 C29 119.4(10) . .
C25 C30 H30 120.3 . .
C29 C30 H30 120.3 . .
C32 C31 C48 115.9(10) . 3_566
C32 C31 C29 117.7(10) . .
C48 C31 C29 126.4(10) 3_566 .
C31 C32 C42 121.2(10) . 3_566
C31 C32 C33 118.3(10) . .
C42 C32 C33 120.5(10) 3_566 .
C34 C33 C32 121.1(10) . .
C34 C33 C42 119.0(10) . .
C32 C33 C42 119.8(10) . .
C35 C34 C33 118.6(10) . .
C35 C34 C28 124.5(10) . .
C33 C34 C28 116.6(10) . .
C34 C35 C36 122.0(10) . .
C34 C35 C40 119.2(10) . .
C36 C35 C40 118.3(10) . .
C37 C36 C35 121.5(11) . .
C37 C36 H36 119.2 . .
C35 C36 H36 119.2 . .
C38 C37 C36 120.3(11) . .
C38 C37 H37 119.8 . .
C36 C37 H37 119.8 . .
C39 C38 C37 120.7(11) . .
C39 C38 H38 119.6 . .
C37 C38 H38 119.6 . .
C38 C39 C40 122.0(11) . .
C38 C39 H39 119.0 . .
C40 C39 H39 119.0 . .
C41 C40 C35 120.1(10) . .
C41 C40 C39 122.1(10) . .
C35 C40 C39 116.9(11) . .
C42 C41 C40 117.7(10) . .
C42 C41 C43 118.5(10) . .
C40 C41 C43 123.8(10) . .
C41 C42 C32 120.5(10) . 3_566
C41 C42 C33 119.9(10) . .
C32 C42 C33 119.7(10) 3_566 .
C44 C43 C41 126.4(11) . .
C44 C43 C48 116.5(10) . .
C41 C43 C48 117.0(10) . .
C45 C44 F7 116.7(11) . .
C45 C44 C43 125.0(11) . .
F7 C44 C43 118.0(11) . .
C44 C45 C46 117.4(11) . .
C44 C45 H45 121.3 . .
C46 C45 H45 121.3 . .
F8 C46 C47 119.4(11) . .
F8 C46 C45 117.2(10) . .
C47 C46 C45 122.8(11) . .
C46 C47 C48 120.1(11) . .
C46 C47 H47 120.0 . .
C48 C47 H47 120.0 . .
C47 C48 C31 120.8(10) . 3_566
C47 C48 C43 117.6(10) . .
C31 C48 C43 121.0(10) 3_566 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C24 1.355(16) 3_656
C1 F1 1.365(12) .
C1 C2 1.360(15) .
C2 C3 1.388(15) .
C2 H2 0.9500 .
C3 C4 1.419(15) .
C3 C22 1.458(15) 3_656
C4 C13 1.401(15) .
C4 C5 1.506(15) .
C5 C10 1.393(15) .
C5 C6 1.408(14) .
C6 C7 1.391(15) .
C6 H6 0.9500 .
C7 C8 1.360(16) .
C7 F2 1.368(13) .
C8 C9 1.380(15) .
C8 H8 0.9500 .
C9 F3 1.351(12) .
C9 C10 1.429(15) .
C10 C11 1.440(15) .
C11 C12 1.376(15) .
C11 C17 1.481(15) .
C12 C14 1.439(15) .
C12 C13 1.442(14) .
C13 C14 1.463(15) 3_656
C14 C15 1.377(15) .
C14 C13 1.463(15) 3_656
C15 C22 1.422(16) .
C15 C16 1.498(15) .
C16 C17 1.392(15) .
C16 C21 1.395(15) .
C17 C18 1.391(15) .
C18 C19 1.392(16) .
C18 H18 0.9500 .
C19 C20 1.393(17) .
C19 H19 0.9500 .
C20 C21 1.346(16) .
C20 H20 0.9500 .
C21 H21 0.9500 .
C22 C23 1.425(15) .
C22 C3 1.458(15) 3_656
C23 F4 1.345(12) .
C23 C24 1.383(16) .
C24 C1 1.355(16) 3_656
C24 H24 0.9500 .
C25 C30 1.334(16) .
C25 F5 1.368(13) .
C25 C26 1.425(16) .
C26 C27 1.384(16) .
C26 H26 0.9500 .
C27 F6 1.363(13) .
C27 C28 1.394(16) .
C28 C29 1.404(16) .
C28 C34 1.470(15) .
C29 C30 1.406(16) .
C29 C31 1.462(15) .
C30 H30 0.9500 .
C31 C32 1.423(15) .
C31 C48 1.447(15) 3_566
C32 C42 1.419(16) 3_566
C32 C33 1.445(15) .
C33 C34 1.413(15) .
C33 C42 1.461(15) .
C34 C35 1.420(15) .
C35 C36 1.419(15) .
C35 C40 1.436(15) .
C36 C37 1.382(16) .
C36 H36 0.9500 .
C37 C38 1.369(18) .
C37 H37 0.9500 .
C38 C39 1.361(17) .
C38 H38 0.9500 .
C39 C40 1.442(15) .
C39 H39 0.9500 .
C40 C41 1.427(16) .
C41 C42 1.401(16) .
C41 C43 1.443(16) .
C42 C32 1.419(16) 3_566
C43 C44 1.369(17) .
C43 C48 1.464(16) .
C44 C45 1.353(17) .
C44 F7 1.360(13) .
C45 C46 1.363(16) .
C45 H45 0.9500 .
C46 F8 1.350(13) .
C46 C47 1.358(16) .
C47 C48 1.406(16) .
C47 H47 0.9500 .
C48 C31 1.447(15) 3_566
