#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/87/2238736.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2238736
loop_
_publ_author_name
'Bender, Christopher O.'
'Boeré, René T.'
_publ_section_title
;
 (5Z,7Z,9Z)-5,10-Dibromobenzo[8]annulene
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1641
_journal_paper_doi               10.1107/S1600536813027797
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H8 Br2'
_chemical_formula_moiety         'C12 H8 Br2'
_chemical_formula_sum            'C12 H8 Br2'
_chemical_formula_weight         312.00
_chemical_melting_point          366
_chemical_name_common
;
3,8-Dibromobenzocyclo-octateraene
;
_chemical_name_systematic
;
(5Z,7Z,9Z)-5,10-Dibromobenzo[8]annulene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 105.2980(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5289(5)
_cell_length_b                   8.3630(5)
_cell_length_c                   15.5645(9)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.97
_cell_measurement_theta_min      2.48
_cell_volume                     1070.83(11)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2008)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 66.06
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15053
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         27.387
_diffrn_reflns_theta_min         2.476
_exptl_absorpt_coefficient_mu    7.524
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.463
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0171P)²+0.5892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0385
_refine_ls_wR_factor_ref         0.0394
_reflns_number_gt                2217
_reflns_number_total             2426
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5345.cif
_cod_data_source_block           I
_cod_database_code               2238736
#BEGIN Tags that were not found in dictionaries:
_shelx_estimated_absorpt_t_min   0.452
_shelx_estimated_absorpt_t_max   0.532
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Br Br1 0.00196(2) 0.47441(2) 0.12658(2) 0.02901(6) Uani d 1
Br Br2 0.33582(2) 0.24542(2) -0.10638(2) 0.02977(6) Uani d 1
C C1 0.2640(2) -0.0177(2) 0.03420(12) 0.0251(4) Uani d 1
H H1 0.3169 -0.0572 -0.0081 0.030 Uiso calc 1
C C2 0.1703(2) -0.1200(2) 0.06965(13) 0.0289(4) Uani d 1
H H2 0.1598 -0.2291 0.0522 0.035 Uiso calc 1
C C3 0.0918(2) -0.0629(2) 0.13055(12) 0.0287(4) Uani d 1
H H3 0.0285 -0.1332 0.1557 0.034 Uiso calc 1
C C4 0.1056(2) 0.0963(2) 0.15478(11) 0.0240(4) Uani d 1
H H4 0.0496 0.1351 0.1958 0.029 Uiso calc 1
C C4A 0.20053(19) 0.2013(2) 0.11986(10) 0.0187(3) Uani d 1
C C5 0.2100(2) 0.3709(2) 0.14745(11) 0.0210(3) Uani d 1
C C6 0.3398(2) 0.4538(2) 0.19030(12) 0.0264(4) Uani d 1
H H6 0.3235 0.5615 0.2054 0.032 Uiso calc 1
C C7 0.5062(2) 0.3917(2) 0.21606(12) 0.0282(4) Uani d 1
H H7 0.5615 0.3944 0.2776 0.034 Uiso calc 1
C C8 0.5866(2) 0.3322(2) 0.16108(12) 0.0270(4) Uani d 1
H H8 0.6935 0.2938 0.1867 0.032 Uiso calc 1
C C9 0.5240(2) 0.3205(2) 0.06401(12) 0.0239(4) Uani d 1
H H9 0.5851 0.3714 0.0289 0.029 Uiso calc 1
C C10 0.3892(2) 0.2449(2) 0.02106(11) 0.0206(3) Uani d 1
C C10A 0.28235(19) 0.1430(2) 0.05945(11) 0.0187(3) Uani d 1
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'
Br Br -0.2901 2.4595 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -0.50 0.0480
0.00 0.00 0.50 0.0720
-1.00 0.00 0.00 0.0420
-1.00 -1.00 0.00 0.0400
1.00 1.00 0.00 0.0490
1.00 -1.00 -1.00 0.0430
-1.00 1.00 1.00 0.0800
-1.00 1.00 0.00 0.0440
1.00 -1.00 0.00 0.0440
0.00 2.00 -0.50 0.0500
0.00 -2.00 0.50 0.0560
1.00 -2.00 -0.50 0.0290
-1.00 2.00 0.50 0.0740
1.00 2.00 -1.00 0.0350
1.00 2.00 -0.50 0.0090
-1.00 -2.00 0.50 0.0340
-1.00 -2.00 1.00 0.0550
0.00 1.00 0.00 0.0440
0.00 -1.00 0.00 0.0400
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C10A 121.12(17)
C2 C1 H1 119.4
C10A C1 H1 119.4
C3 C2 C1 119.75(17)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 119.95(17)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C4A 121.04(17)
C3 C4 H4 119.5
C4A C4 H4 119.5
C10A C4A C4 119.05(16)
C10A C4A C5 122.07(15)
C4 C4A C5 118.88(15)
C6 C5 C4A 128.45(16)
C6 C5 Br1 117.39(13)
C4A C5 Br1 113.91(12)
C5 C6 C7 124.91(17)
C5 C6 H6 117.5
C7 C6 H6 117.5
C8 C7 C6 125.79(16)
C8 C7 H7 117.1
C6 C7 H7 117.1
C7 C8 C9 125.45(17)
C7 C8 H8 117.3
C9 C8 H8 117.3
C10 C9 C8 125.57(16)
C10 C9 H9 117.2
C8 C9 H9 117.2
C9 C10 C10A 127.81(16)
C9 C10 Br2 117.29(13)
C10A C10 Br2 114.52(12)
C1 C10A C4A 119.06(16)
C1 C10A C10 118.30(15)
C4A C10A C10 122.64(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.9234(17)
Br2 C10 1.9145(17)
C1 C2 1.382(3)
C1 C10A 1.397(2)
C1 H1 0.9500
C2 C3 1.381(3)
C2 H2 0.9500
C3 C4 1.380(3)
C3 H3 0.9500
C4 C4A 1.398(2)
C4 H4 0.9500
C4A C10A 1.398(2)
C4A C5 1.478(2)
C5 C6 1.327(2)
C6 C7 1.465(3)
C6 H6 0.9500
C7 C8 1.326(3)
C7 H7 0.9500
C8 C9 1.467(3)
C8 H8 0.9500
C9 C10 1.327(2)
C9 H9 0.9500
C10 C10A 1.484(2)
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
C10A C1 C2 C3 0.6(3)
C1 C2 C3 C4 0.9(3)
C2 C3 C4 C4A -1.2(3)
C3 C4 C4A C10A 0.0(2)
C3 C4 C4A C5 179.50(16)
C10A C4A C5 C6 -62.3(2)
C4 C4A C5 C6 118.2(2)
C10A C4A C5 Br1 123.72(14)
C4 C4A C5 Br1 -55.72(18)
C4A C5 C6 C7 2.9(3)
Br1 C5 C6 C7 176.62(14)
C5 C6 C7 C8 58.2(3)
C6 C7 C8 C9 1.3(3)
C7 C8 C9 C10 -57.1(3)
C8 C9 C10 C10A -6.8(3)
C8 C9 C10 Br2 -179.26(14)
C2 C1 C10A C4A -1.7(2)
C2 C1 C10A C10 177.97(15)
C4 C4A C10A C1 1.4(2)
C5 C4A C10A C1 -178.05(15)
C4 C4A C10A C10 -178.29(15)
C5 C4A C10A C10 2.3(2)
C9 C10 C10A C1 -118.0(2)
Br2 C10 C10A C1 54.57(18)
C9 C10 C10A C4A 61.7(2)
Br2 C10 C10A C4A -125.75(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5705470
