#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/30/7213091.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213091
loop_
_publ_author_name
'Yu, Richeng'
'Yakimansky, Alexander'
'Voigt-Martin, Ingrid G.'
'Fetten, Michael'
'Schnorpfeil, C.'
'Schollmeyer, Dieter'
'Meier, Herbert'
_publ_section_title
;
 Tetrabenzo[ab,  f, jk,o][18]annulene: synthesis,
 crystal structure analysis, ab initio quantum-chemical studies of
 intermolecular interactions in the gas phase and in crystalline states,
 photodimerization and photopolymerization
;
_journal_issue                   9
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              1881
_journal_paper_doi               10.1039/a903451j
_journal_year                    1999
_chemical_formula_sum            'C32 H24'
_chemical_formula_weight         408.54
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   28.1031(12)
_cell_length_b                   28.1031(12)
_cell_length_c                   7.1509(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      20
_cell_volume                     4891.0(4)
_computing_cell_refinement       'Enraf Nonius Software V5'
_computing_data_collection       'Enraf Nonius Software V5'
_computing_data_reduction        'Corinc (Dräger, 1971)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir-92 (Altomare,1994)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_device_type  'CAD4 Enraf Nonius'
_diffrn_measurement_method       θ/2ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2783
_diffrn_reflns_theta_full        74.84
_diffrn_reflns_theta_max         74.84
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    'riding refU'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0516
_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)+(0.0581P)²+1.3084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                1485
_reflns_number_total             2234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            903451jsup1.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7213091
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.22021(9) 0.12794(9) 0.6826(3) 0.0404(5) Uani 1 1 d .
H1 H 0.2609 0.1393 0.6691 0.055(7) Uiso 1 1 d R
C2 C 0.19134(8) 0.09789(8) 0.8389(3) 0.0388(5) Uani 1 1 d .
C3 C 0.13503(9) 0.07956(9) 0.8483(3) 0.0445(5) Uani 1 1 d .
H3 H 0.1120 0.0606 0.9603 0.051(6) Uiso 1 1 d R
C4 C 0.10937(9) 0.09141(10) 0.7049(3) 0.0485(6) Uani 1 1 d .
H4 H 0.0670 0.0781 0.7213 0.051(7) Uiso 1 1 d R
C5 C 0.13848(9) 0.12093(9) 0.5510(3) 0.0430(5) Uani 1 1 d .
H5 H 0.1204 0.1291 0.4394 0.042(6) Uiso 1 1 d R
C6 C 0.19506(8) 0.14039(8) 0.5375(3) 0.0390(5) Uani 1 1 d .
C7 C 0.22582(9) 0.17061(9) 0.3710(3) 0.0422(5) Uani 1 1 d .
H7 H 0.2034 0.1662 0.2679 0.057(7) Uiso 1 1 d R
C8 C 0.28010(9) 0.20088(9) 0.3589(3) 0.0413(5) Uani 1 1 d .
H8 H 0.2984 0.2031 0.4740 0.047(6) Uiso 1 1 d R
C9 C 0.31179(9) 0.22758(8) 0.1894(3) 0.0388(5) Uani 1 1 d .
C10 C 0.28733(10) 0.23983(9) 0.0399(3) 0.0467(5) Uani 1 1 d .
H10 H 0.2506 0.2362 0.0686 0.058(7) Uiso 1 1 d R
C11 C 0.31518(10) 0.26170(9) -0.1243(3) 0.0496(6) Uani 1 1 d .
H11 H 0.2943 0.2664 -0.2307 0.066(8) Uiso 1 1 d R
C12 C 0.36834(10) 0.27164(9) -0.1461(3) 0.0466(5) Uani 1 1 d .
H12 H 0.3856 0.2891 -0.2685 0.059(7) Uiso 1 1 d R
C13 C 0.39388(9) 0.26124(9) 0.0008(3) 0.0435(5) Uani 1 1 d .
H13 H 0.4347 0.2721 -0.0080 0.055(7) Uiso 1 1 d R
C14 C 0.36695(9) 0.23987(8) 0.1703(3) 0.0378(5) Uani 1 1 d .
C15 C 0.39492(9) 0.22799(9) 0.3229(3) 0.0399(5) Uani 1 1 d .
H15 H 0.3705 0.2024 0.4210 0.044(6) Uiso 1 1 d R
C16 C 0.44850(9) 0.24905(9) 0.3427(3) 0.0429(5) Uani 1 1 d .
H16 H 0.4729 0.2758 0.2400 0.062(7) Uiso 1 1 d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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
C2 C1 C6 122.33(19) . .
C2 C1 H1 119.1 . .
C6 C1 H1 118.5 . .
C1 C2 C3 118.10(19) . .
C1 C2 C16 121.94(19) . 13_556
C3 C2 C16 119.95(19) . 13_556
C4 C3 C2 120.3(2) . .
C4 C3 H3 116.5 . .
C2 C3 H3 123.0 . .
C5 C4 C3 120.8(2) . .
C5 C4 H4 121.7 . .
C3 C4 H4 117.4 . .
C4 C5 C6 120.5(2) . .
C4 C5 H5 122.9 . .
C6 C5 H5 116.6 . .
C1 C6 C5 117.9(2) . .
C1 C6 C7 121.54(19) . .
C5 C6 C7 120.45(19) . .
C8 C7 C6 125.44(19) . .
C8 C7 H7 121.0 . .
C6 C7 H7 113.6 . .
C7 C8 C9 126.2(2) . .
C7 C8 H8 113.3 . .
C9 C8 H8 120.5 . .
C10 C9 C14 118.51(19) . .
C10 C9 C8 120.5(2) . .
C14 C9 C8 120.96(18) . .
C11 C10 C9 121.4(2) . .
C11 C10 H10 123.1 . .
C9 C10 H10 115.0 . .
C10 C11 C12 120.2(2) . .
C10 C11 H11 117.7 . .
C12 C11 H11 121.9 . .
C13 C12 C11 119.5(2) . .
C13 C12 H12 126.2 . .
C11 C12 H12 114.0 . .
C12 C13 C14 121.6(2) . .
C12 C13 H13 120.6 . .
C14 C13 H13 117.6 . .
C13 C14 C9 118.72(19) . .
C13 C14 C15 120.21(19) . .
C9 C14 C15 121.00(18) . .
C16 C15 C14 126.45(19) . .
C16 C15 H15 117.9 . .
C14 C15 H15 115.6 . .
C15 C16 C2 125.3(2) . 13_556
C15 C16 H16 116.3 . .
C2 C16 H16 118.3 13_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.391(3) .
C1 C6 1.395(3) .
C1 H1 1.0272 .
C2 C3 1.399(3) .
C2 C16 1.476(3) 13_556
C3 C4 1.387(3) .
C3 H3 0.9993 .
C4 C5 1.374(3) .
C4 H4 1.0612 .
C5 C6 1.402(3) .
C5 H5 1.0317 .
C6 C7 1.467(3) .
C7 C8 1.327(3) .
C7 H7 0.9370 .
C8 C9 1.469(3) .
C8 H8 0.9556 .
C9 C10 1.404(3) .
C9 C14 1.416(3) .
C10 C11 1.374(3) .
C10 H10 1.0054 .
C11 C12 1.385(3) .
C11 H11 1.0091 .
C12 C13 1.384(3) .
C12 H12 1.0021 .
C13 C14 1.396(3) .
C13 H13 1.0299 .
C14 C15 1.477(3) .
C15 C16 1.321(3) .
C15 H15 0.9941 .
C16 C2 1.476(3) 13_556
C16 H16 1.0288 .
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
C6 C1 C2 C3 0.3(3) . .
C6 C1 C2 C16 179.2(2) . 13_556
C1 C2 C3 C4 -0.1(3) . .
C16 C2 C3 C4 -178.9(2) 13_556 .
C2 C3 C4 C5 0.4(3) . .
C3 C4 C5 C6 -1.0(3) . .
C2 C1 C6 C5 -0.9(3) . .
C2 C1 C6 C7 -178.0(2) . .
C4 C5 C6 C1 1.2(3) . .
C4 C5 C6 C7 178.3(2) . .
C1 C6 C7 C8 -18.5(3) . .
C5 C6 C7 C8 164.4(2) . .
C6 C7 C8 C9 174.5(2) . .
C7 C8 C9 C10 23.1(3) . .
C7 C8 C9 C14 -154.8(2) . .
C14 C9 C10 C11 2.0(3) . .
C8 C9 C10 C11 -175.9(2) . .
C9 C10 C11 C12 0.7(4) . .
C10 C11 C12 C13 -2.3(3) . .
C11 C12 C13 C14 1.3(3) . .
C12 C13 C14 C9 1.4(3) . .
C12 C13 C14 C15 178.5(2) . .
C10 C9 C14 C13 -2.9(3) . .
C8 C9 C14 C13 175.0(2) . .
C10 C9 C14 C15 179.94(19) . .
C8 C9 C14 C15 -2.2(3) . .
C13 C14 C15 C16 20.9(3) . .
C9 C14 C15 C16 -162.0(2) . .
C14 C15 C16 C2 -178.5(2) . 13_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15417192
