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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/90/7239088.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_7239088
loop_
_publ_author_name
'Tanaka, Kazuki'
'Aratani, Naoki'
'Kuzuhara, Daiki'
'Sakamoto, Sadaaki'
'Okujima, Tetsuo'
'Ono, Noboru'
'Uno, Hidemitsu'
'Yamada, Hiroko'
_publ_section_title
;
 A soluble bispentacenequinone precursor for creation of directly
 6,6′-linked bispentacenes and a
 tetracyanobipentacenequinodimethane
;
_journal_issue                   35
_journal_name_full               'RSC Advances'
_journal_page_first              15310
_journal_paper_doi               10.1039/c3ra41914b
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C52 H40 O2'
_chemical_formula_sum            'C52 H40 O2'
_chemical_formula_weight         696.84
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.4150(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2853(3)
_cell_length_b                   12.1795(4)
_cell_length_c                   14.7576(5)
_cell_measurement_reflns_used    10511
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      3.29
_cell_volume                     1773.33(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14260
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0668
_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)+(0.1093P)²+1.4566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.1868
_reflns_number_gt                2867
_reflns_number_total             3241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra41914b.txt
_cod_data_source_block           shelxl4
_cod_original_cell_volume        1773.34(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7239088
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.25851(17) 0.18554(13) 0.02544(10) 0.0336(4) Uani 1 1 d .
C1 C 0.2183(2) 0.27960(17) 0.03029(14) 0.0244(5) Uani 1 1 d .
C2 C 0.1774(2) 0.31897(17) 0.11315(13) 0.0229(4) Uani 1 1 d .
C3 C 0.2218(2) 0.26008(17) 0.19818(14) 0.0256(5) Uani 1 1 d .
H3 H 0.2589 0.1886 0.1987 0.031 Uiso 1 1 calc R
C4 C 0.2112(2) 0.30653(18) 0.28069(14) 0.0261(5) Uani 1 1 d .
C5 C 0.2689(2) 0.2613(2) 0.37991(15) 0.0335(5) Uani 1 1 d .
H5 H 0.3035 0.1846 0.3799 0.040 Uiso 1 1 calc R
C6 C 0.1619(2) 0.2710(2) 0.43295(15) 0.0336(5) Uani 1 1 d .
H6 H 0.1348 0.2110 0.4645 0.040 Uiso 1 1 calc R
C7 C 0.1091(2) 0.3730(2) 0.43092(15) 0.0315(5) Uani 1 1 d .
H7 H 0.0405 0.3909 0.4601 0.038 Uiso 1 1 calc R
C8 C 0.1701(2) 0.45669(18) 0.37723(14) 0.0267(5) Uani 1 1 d .
H8 H 0.1287 0.5312 0.3759 0.032 Uiso 1 1 calc R
C9 C 0.15655(19) 0.41287(17) 0.28017(13) 0.0214(4) Uani 1 1 d .
C10 C 0.10516(19) 0.46865(17) 0.19479(13) 0.0220(4) Uani 1 1 d .
H10 H 0.0647 0.5388 0.1942 0.026 Uiso 1 1 calc R
C11 C 0.11322(19) 0.42125(17) 0.10984(13) 0.0212(4) Uani 1 1 d .
C12 C 0.0621(2) 0.47561(16) 0.01564(13) 0.0209(4) Uani 1 1 d .
C13 C 0.15831(19) 0.46512(16) -0.04277(13) 0.0216(4) Uani 1 1 d .
C14 C 0.1846(2) 0.54966(17) -0.09957(14) 0.0237(5) Uani 1 1 d .
H14 H 0.1434 0.6195 -0.1000 0.028 Uiso 1 1 calc R
C15 C 0.2709(2) 0.53124(18) -0.15515(14) 0.0264(5) Uani 1 1 d .
C16 C 0.3071(2) 0.6126(2) -0.22140(17) 0.0348(5) Uani 1 1 d .
H16 H 0.2583 0.6841 -0.2241 0.042 Uiso 1 1 calc R
C17 C 0.2767(3) 0.5564(3) -0.31805(18) 0.0480(7) Uani 1 1 d .
H17 H 0.2190 0.5873 -0.3742 0.058 Uiso 1 1 calc R
C18 C 0.3413(3) 0.4563(3) -0.31566(17) 0.0471(7) Uani 1 1 d .
H18 H 0.3329 0.4118 -0.3699 0.056 Uiso 1 1 calc R
C19 C 0.4269(2) 0.4253(2) -0.21757(16) 0.0348(6) Uani 1 1 d .
H19 H 0.4712 0.3520 -0.2163 0.042 Uiso 1 1 calc R
C20 C 0.3350(2) 0.42936(19) -0.15361(14) 0.0274(5) Uani 1 1 d .
C21 C 0.3143(2) 0.34702(18) -0.09548(14) 0.0259(5) Uani 1 1 d .
H21 H 0.3592 0.2785 -0.0933 0.031 Uiso 1 1 calc R
C22 C 0.2267(2) 0.36480(17) -0.03954(13) 0.0232(5) Uani 1 1 d .
C23 C 0.5309(3) 0.5183(2) -0.1850(2) 0.0473(7) Uani 1 1 d .
H23A H 0.5872 0.5034 -0.1197 0.057 Uiso 1 1 calc R
H23B H 0.5916 0.5208 -0.2264 0.057 Uiso 1 1 calc R
C24 C 0.4622(3) 0.6259(2) -0.1879(2) 0.0483(7) Uani 1 1 d .
H24A H 0.4914 0.6759 -0.2314 0.058 Uiso 1 1 calc R
H24B H 0.4890 0.6593 -0.1242 0.058 Uiso 1 1 calc R
C25 C 0.3833(2) 0.3440(2) 0.43022(15) 0.0357(6) Uani 1 1 d .
H25A H 0.4228 0.3217 0.4969 0.043 Uiso 1 1 calc R
H25B H 0.4563 0.3430 0.3986 0.043 Uiso 1 1 calc R
C26 C 0.3261(2) 0.4572(2) 0.42646(15) 0.0320(5) Uani 1 1 d .
H26A H 0.3716 0.5060 0.3912 0.038 Uiso 1 1 calc R
H26B H 0.3437 0.4865 0.4914 0.038 Uiso 1 1 calc R
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'
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
O1 C1 C2 121.98(18) .
O1 C1 C22 121.75(18) .
C2 C1 C22 115.69(17) .
C11 C2 C3 120.98(18) .
C11 C2 C1 119.93(17) .
C3 C2 C1 118.43(18) .
C4 C3 C2 119.61(19) .
C4 C3 H3 120.2 .
C2 C3 H3 120.2 .
C3 C4 C9 120.27(18) .
C3 C4 C5 126.7(2) .
C9 C4 C5 112.62(18) .
C4 C5 C6 108.92(18) .
C4 C5 C25 105.07(18) .
C6 C5 C25 105.14(18) .
C4 C5 H5 112.4 .
C6 C5 H5 112.4 .
C25 C5 H5 112.4 .
C7 C6 C5 113.81(19) .
C7 C6 H6 123.1 .
C5 C6 H6 123.1 .
C6 C7 C8 113.72(19) .
C6 C7 H7 123.1 .
C8 C7 H7 123.1 .
C9 C8 C7 108.47(17) .
C9 C8 C26 104.58(17) .
C7 C8 C26 106.24(17) .
C9 C8 H8 112.4 .
C7 C8 H8 112.4 .
C26 C8 H8 112.4 .
C10 C9 C4 119.99(18) .
C10 C9 C8 126.76(19) .
C4 C9 C8 113.12(17) .
C9 C10 C11 120.17(18) .
C9 C10 H10 119.9 .
C11 C10 H10 119.9 .
C10 C11 C2 118.66(17) .
C10 C11 C12 123.66(18) .
C2 C11 C12 117.63(17) .
C12 C12 C13 123.5(2) 3_565
C12 C12 C11 123.8(2) 3_565
C13 C12 C11 112.54(16) .
C14 C13 C22 118.68(18) .
C14 C13 C12 123.72(18) .
C22 C13 C12 117.59(17) .
C15 C14 C13 119.94(19) .
C15 C14 H14 120.0 .
C13 C14 H14 120.0 .
C14 C15 C20 120.69(19) .
C14 C15 C16 126.3(2) .
C20 C15 C16 112.96(18) .
C15 C16 C17 106.7(2) .
C15 C16 C24 106.51(19) .
C17 C16 C24 105.4(2) .
C15 C16 H16 112.6 .
C17 C16 H16 112.6 .
C24 C16 H16 112.6 .
C18 C17 C16 113.5(2) .
C18 C17 H17 123.2 .
C16 C17 H17 123.2 .
C17 C18 C19 112.9(2) .
C17 C18 H18 123.6 .
C19 C18 H18 123.6 .
C20 C19 C18 106.95(18) .
C20 C19 C23 106.43(19) .
C18 C19 C23 106.3(2) .
C20 C19 H19 112.2 .
C18 C19 H19 112.2 .
C23 C19 H19 112.2 .
C21 C20 C15 120.03(19) .
C21 C20 C19 126.8(2) .
C15 C20 C19 113.09(19) .
C20 C21 C22 119.6(2) .
C20 C21 H21 120.2 .
C22 C21 H21 120.2 .
C21 C22 C13 120.96(19) .
C21 C22 C1 118.38(18) .
C13 C22 C1 120.38(17) .
C24 C23 C19 111.0(2) .
C24 C23 H23A 109.4 .
C19 C23 H23A 109.4 .
C24 C23 H23B 109.4 .
C19 C23 H23B 109.4 .
H23A C23 H23B 108.0 .
C23 C24 C16 111.0(2) .
C23 C24 H24A 109.4 .
C16 C24 H24A 109.4 .
C23 C24 H24B 109.4 .
C16 C24 H24B 109.4 .
H24A C24 H24B 108.0 .
C26 C25 C5 109.92(18) .
C26 C25 H25A 109.7 .
C5 C25 H25A 109.7 .
C26 C25 H25B 109.7 .
C5 C25 H25B 109.7 .
H25A C25 H25B 108.2 .
C25 C26 C8 110.79(18) .
C25 C26 H26A 109.5 .
C8 C26 H26A 109.5 .
C25 C26 H26B 109.5 .
C8 C26 H26B 109.5 .
H26A C26 H26B 108.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.227(3) .
C1 C2 1.481(3) .
C1 C22 1.482(3) .
C2 C11 1.404(3) .
C2 C3 1.405(3) .
C3 C4 1.375(3) .
C3 H3 0.9500 .
C4 C9 1.411(3) .
C4 C5 1.519(3) .
C5 C6 1.525(3) .
C5 C25 1.568(4) .
C5 H5 1.0000 .
C6 C7 1.352(3) .
C6 H6 0.9500 .
C7 C8 1.531(3) .
C7 H7 0.9500 .
C8 C9 1.498(3) .
C8 C26 1.564(3) .
C8 H8 1.0000 .
C9 C10 1.397(3) .
C10 C11 1.404(3) .
C10 H10 0.9500 .
C11 C12 1.495(3) .
C12 C12 1.365(4) 3_565
C12 C13 1.490(3) .
C13 C14 1.402(3) .
C13 C22 1.404(3) .
C14 C15 1.386(3) .
C14 H14 0.9500 .
C15 C20 1.402(3) .
C15 C16 1.511(3) .
C16 C17 1.532(4) .
C16 C24 1.540(3) .
C16 H16 1.0000 .
C17 C18 1.385(4) .
C17 H17 0.9500 .
C18 C19 1.514(3) .
C18 H18 0.9500 .
C19 C20 1.513(3) .
C19 C23 1.538(4) .
C19 H19 1.0000 .
C20 C21 1.375(3) .
C21 C22 1.401(3) .
C21 H21 0.9500 .
C23 C24 1.484(4) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 C26 1.494(3) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C11 -170.49(19) . .
C22 C1 C2 C11 18.1(3) . .
O1 C1 C2 C3 18.7(3) . .
C22 C1 C2 C3 -152.68(19) . .
C11 C2 C3 C4 -4.7(3) . .
C1 C2 C3 C4 165.95(19) . .
C2 C3 C4 C9 -0.2(3) . .
C2 C3 C4 C5 -172.1(2) . .
C3 C4 C5 C6 -135.6(2) . .
C9 C4 C5 C6 52.0(3) . .
C3 C4 C5 C25 112.2(2) . .
C9 C4 C5 C25 -60.2(2) . .
C4 C5 C6 C7 -52.2(3) . .
C25 C5 C6 C7 60.0(2) . .
C5 C6 C7 C8 -1.0(3) . .
C6 C7 C8 C9 54.4(2) . .
C6 C7 C8 C26 -57.5(2) . .
C3 C4 C9 C10 4.0(3) . .
C5 C4 C9 C10 176.91(18) . .
C3 C4 C9 C8 -172.06(19) . .
C5 C4 C9 C8 0.9(2) . .
C7 C8 C9 C10 130.7(2) . .
C26 C8 C9 C10 -116.3(2) . .
C7 C8 C9 C4 -53.6(2) . .
C26 C8 C9 C4 59.5(2) . .
C4 C9 C10 C11 -2.9(3) . .
C8 C9 C10 C11 172.61(18) . .
C9 C10 C11 C2 -2.0(3) . .
C9 C10 C11 C12 -179.39(17) . .
C3 C2 C11 C10 5.8(3) . .
C1 C2 C11 C10 -164.74(18) . .
C3 C2 C11 C12 -176.61(18) . .
C1 C2 C11 C12 12.8(3) . .
C10 C11 C12 C12 -47.0(3) . 3_565
C2 C11 C12 C12 135.5(3) . 3_565
C10 C11 C12 C13 136.30(19) . .
C2 C11 C12 C13 -41.1(2) . .
C12 C12 C13 C14 42.9(3) 3_565 .
C11 C12 C13 C14 -140.43(19) . .
C12 C12 C13 C22 -137.7(2) 3_565 .
C11 C12 C13 C22 39.0(2) . .
C22 C13 C14 C15 3.6(3) . .
C12 C13 C14 C15 -176.96(18) . .
C13 C14 C15 C20 -1.5(3) . .
C13 C14 C15 C16 178.6(2) . .
C14 C15 C16 C17 -126.3(2) . .
C20 C15 C16 C17 53.8(2) . .
C14 C15 C16 C24 121.5(2) . .
C20 C15 C16 C24 -58.4(3) . .
C15 C16 C17 C18 -55.0(3) . .
C24 C16 C17 C18 58.0(3) . .
C16 C17 C18 C19 0.2(3) . .
C17 C18 C19 C20 55.0(3) . .
C17 C18 C19 C23 -58.4(3) . .
C14 C15 C20 C21 -1.0(3) . .
C16 C15 C20 C21 178.86(19) . .
C14 C15 C20 C19 -179.06(19) . .
C16 C15 C20 C19 0.8(3) . .
C18 C19 C20 C21 126.3(2) . .
C23 C19 C20 C21 -120.4(2) . .
C18 C19 C20 C15 -55.8(3) . .
C23 C19 C20 C15 57.5(2) . .
C15 C20 C21 C22 1.4(3) . .
C19 C20 C21 C22 179.1(2) . .
C20 C21 C22 C13 0.8(3) . .
C20 C21 C22 C1 -173.15(19) . .
C14 C13 C22 C21 -3.2(3) . .
C12 C13 C22 C21 177.27(18) . .
C14 C13 C22 C1 170.55(18) . .
C12 C13 C22 C1 -8.9(3) . .
O1 C1 C22 C21 -17.7(3) . .
C2 C1 C22 C21 153.73(18) . .
O1 C1 C22 C13 168.36(19) . .
C2 C1 C22 C13 -20.2(3) . .
C20 C19 C23 C24 -57.0(3) . .
C18 C19 C23 C24 56.7(3) . .
C19 C23 C24 C16 0.8(3) . .
C15 C16 C24 C23 56.2(3) . .
C17 C16 C24 C23 -56.9(3) . .
C4 C5 C25 C26 56.5(2) . .
C6 C5 C25 C26 -58.4(2) . .
C5 C25 C26 C8 2.2(2) . .
C9 C8 C26 C25 -59.9(2) . .
C7 C8 C26 C25 54.7(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168340702
