#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/71/7107129.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_7107129
loop_
_publ_author_name
'Kamaljit Singh'
'Tarunpreet Singh Virk'
'Jing Zhang'
'Wei Xu'
'Daoben Zhu'
_publ_section_title
;
 Oxygen bridged neutral annulenes: a novel class of materials for organic
 field-effect transistors
;
_journal_name_full               Chem.Commun.
_journal_page_first              121
_journal_paper_doi               10.1039/c1cc16344b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C34 H22 O4'
_chemical_formula_weight         494.52
_space_group_IT_number           14
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.03(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.091(3)
_cell_length_b                   9.1718(12)
_cell_length_c                   10.744(2)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.1495
_cell_measurement_theta_min      3.6558
_cell_volume                     1233.4(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'OXFORD DIFFRACTION XCALIBUR-S'
_diffrn_measurement_method       ω/q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8079
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.100
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0356
_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)+(0.0419P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                1340
_reflns_number_total             2158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc16344b.txt
_cod_data_source_block           gnu049
_cod_original_cell_volume        1233.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7107129
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
O1 O 0.09037(8) 0.20527(9) 0.36170(9) 0.0481(3) Uani 1 1 d .
O2 O 0.15311(8) -0.04427(10) 0.43687(9) 0.0494(3) Uani 1 1 d .
C1 C 0.03594(12) 0.33457(14) 0.35094(13) 0.0464(4) Uani 1 1 d .
C2 C -0.04897(12) 0.33542(15) 0.40343(13) 0.0483(4) Uani 1 1 d .
H2 H -0.0889 0.4200 0.3997 0.058 Uiso 1 1 calc R
C3 C 0.08395(12) 0.43158(17) 0.28747(14) 0.0551(4) Uani 1 1 d .
H3 H 0.0634 0.5279 0.2673 0.066 Uiso 1 1 calc R
C4 C 0.16742(13) 0.36160(16) 0.25903(15) 0.0548(4) Uani 1 1 d .
H4 H 0.2128 0.4018 0.2159 0.066 Uiso 1 1 calc R
C5 C 0.17167(12) 0.22004(15) 0.30633(13) 0.0457(4) Uani 1 1 d .
C6 C 0.24034(12) 0.10144(15) 0.31372(13) 0.0456(4) Uani 1 1 d .
C7 C 0.32814(12) 0.11179(15) 0.25308(14) 0.0480(4) Uani 1 1 d .
C8 C 0.30834(13) 0.14103(16) 0.12205(15) 0.0565(4) Uani 1 1 d .
H8 H 0.2390 0.1609 0.0713 0.068 Uiso 1 1 calc R
C9 C 0.39034(15) 0.14107(18) 0.06590(17) 0.0674(5) Uani 1 1 d .
H9 H 0.3759 0.1613 -0.0224 0.081 Uiso 1 1 calc R
C10 C 0.49226(16) 0.11184(19) 0.1382(2) 0.0732(6) Uani 1 1 d .
H10 H 0.5468 0.1096 0.0990 0.088 Uiso 1 1 calc R
C11 C 0.51459(15) 0.0857(2) 0.26905(19) 0.0796(6) Uani 1 1 d .
H11 H 0.5844 0.0679 0.3193 0.096 Uiso 1 1 calc R
C12 C 0.43263(13) 0.0859(2) 0.32548(16) 0.0694(5) Uani 1 1 d .
H12 H 0.4480 0.0683 0.4143 0.083 Uiso 1 1 calc R
C13 C 0.23009(12) -0.02991(15) 0.37493(13) 0.0452(4) Uani 1 1 d .
C14 C 0.28154(13) -0.16322(16) 0.38370(16) 0.0592(4) Uani 1 1 d .
H14 H 0.3379 -0.1845 0.3504 0.071 Uiso 1 1 calc R
C15 C 0.23553(13) -0.25823(17) 0.44942(16) 0.0599(5) Uani 1 1 d .
H15 H 0.2554 -0.3548 0.4690 0.072 Uiso 1 1 calc R
C16 C 0.15435(12) -0.18545(15) 0.48168(13) 0.0483(4) Uani 1 1 d .
C17 C 0.07457(12) -0.21311(15) 0.53929(13) 0.0484(4) Uani 1 1 d .
H17 H 0.0302 -0.1339 0.5390 0.058 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
C5 O1 C1 109.19(10) .
C13 O2 C16 108.98(10) .
O1 C1 C3 107.38(13) .
O1 C1 C2 115.44(12) .
C3 C1 C2 137.17(13) .
C17 C2 C1 120.66(13) 3_556
C17 C2 H2 119.7 3_556
C1 C2 H2 119.7 .
C4 C3 C1 108.38(13) .
C4 C3 H3 125.8 .
C1 C3 H3 125.8 .
C3 C4 C5 107.69(14) .
C3 C4 H4 126.2 .
C5 C4 H4 126.2 .
O1 C5 C4 107.36(13) .
O1 C5 C6 117.82(12) .
C4 C5 C6 134.74(15) .
C13 C6 C5 123.26(13) .
C13 C6 C7 117.14(12) .
C5 C6 C7 119.60(13) .
C8 C7 C12 117.81(15) .
C8 C7 C6 121.51(14) .
C12 C7 C6 120.61(14) .
C9 C8 C7 120.59(16) .
C9 C8 H8 119.7 .
C7 C8 H8 119.7 .
C10 C9 C8 120.67(17) .
C10 C9 H9 119.7 .
C8 C9 H9 119.7 .
C9 C10 C11 119.98(17) .
C9 C10 H10 120.0 .
C11 C10 H10 120.0 .
C10 C11 C12 119.42(18) .
C10 C11 H11 120.3 .
C12 C11 H11 120.3 .
C11 C12 C7 121.49(16) .
C11 C12 H12 119.3 .
C7 C12 H12 119.3 .
O2 C13 C14 107.15(13) .
O2 C13 C6 119.88(12) .
C14 C13 C6 132.90(14) .
C15 C14 C13 108.58(14) .
C15 C14 H14 125.7 .
C13 C14 H14 125.7 .
C14 C15 C16 108.00(13) .
C14 C15 H15 126.0 .
C16 C15 H15 126.0 .
O2 C16 C15 107.28(12) .
O2 C16 C17 113.24(12) .
C15 C16 C17 139.43(14) .
C2 C17 C16 131.90(14) 3_556
C2 C17 H17 114.0 3_556
C16 C17 H17 114.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.3695(16) .
O1 C1 1.3709(16) .
O2 C13 1.3669(16) .
O2 C16 1.3799(16) .
C1 C3 1.379(2) .
C1 C2 1.3859(19) .
C2 C17 1.3676(18) 3_556
C2 H2 0.9300 .
C3 C4 1.376(2) .
C3 H3 0.9300 .
C4 C5 1.3895(19) .
C4 H4 0.9300 .
C5 C6 1.3986(19) .
C6 C13 1.3976(18) .
C6 C7 1.481(2) .
C7 C8 1.381(2) .
C7 C12 1.382(2) .
C8 C9 1.377(2) .
C8 H8 0.9300 .
C9 C10 1.360(2) .
C9 H9 0.9300 .
C10 C11 1.370(2) .
C10 H10 0.9300 .
C11 C12 1.378(2) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.3858(19) .
C14 C15 1.367(2) .
C14 H14 0.9300 .
C15 C16 1.382(2) .
C15 H15 0.9300 .
C16 C17 1.3846(19) .
C17 C2 1.3676(18) 3_556
C17 H17 0.9300 .
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_4
C5 O1 C1 C3 0.15(15) .
C5 O1 C1 C2 -179.91(12) .
O1 C1 C2 C17 -0.3(2) 3_556
C3 C1 C2 C17 179.61(17) 3_556
O1 C1 C3 C4 0.20(16) .
C2 C1 C3 C4 -179.72(17) .
C1 C3 C4 C5 -0.46(17) .
C1 O1 C5 C4 -0.43(15) .
C1 O1 C5 C6 176.67(12) .
C3 C4 C5 O1 0.55(16) .
C3 C4 C5 C6 -175.84(16) .
O1 C5 C6 C13 -0.3(2) .
C4 C5 C6 C13 175.84(15) .
O1 C5 C6 C7 178.91(12) .
C4 C5 C6 C7 -5.0(2) .
C13 C6 C7 C8 121.23(15) .
C5 C6 C7 C8 -58.00(19) .
C13 C6 C7 C12 -55.9(2) .
C5 C6 C7 C12 124.88(16) .
C12 C7 C8 C9 1.3(2) .
C6 C7 C8 C9 -175.86(14) .
C7 C8 C9 C10 0.2(2) .
C8 C9 C10 C11 -1.7(3) .
C9 C10 C11 C12 1.5(3) .
C10 C11 C12 C7 0.1(3) .
C8 C7 C12 C11 -1.5(3) .
C6 C7 C12 C11 175.73(16) .
C16 O2 C13 C14 -1.27(15) .
C16 O2 C13 C6 176.07(12) .
C5 C6 C13 O2 -3.2(2) .
C7 C6 C13 O2 177.57(12) .
C5 C6 C13 C14 173.29(16) .
C7 C6 C13 C14 -5.9(2) .
O2 C13 C14 C15 0.54(18) .
C6 C13 C14 C15 -176.30(16) .
C13 C14 C15 C16 0.38(19) .
C13 O2 C16 C15 1.50(16) .
C13 O2 C16 C17 -176.36(12) .
C14 C15 C16 O2 -1.15(18) .
C14 C15 C16 C17 175.84(18) .
O2 C16 C17 C2 -179.02(14) 3_556
C15 C16 C17 C2 4.1(3) 3_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101545801
