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#$Date: 2022-06-16 12:18:31 +0300 (Thu, 16 Jun 2022) $
#$Revision: 276067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105428.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_8105428
loop_
_publ_author_name
'Lo, Kong Mun'
'Lee, See Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of 4,4′-(oxybis(methylene))bis(bromobenzene),
 C14H12Br2O
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1227
_journal_page_last               1229
_journal_paper_doi               10.1515/ncrs-2020-0280
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 Br2 O'
_chemical_formula_sum            'C14 H12 Br2 O'
_chemical_formula_weight         356.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.1700(8)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   29.7356(3)
_cell_length_b                   5.88712(4)
_cell_length_c                   11.10915(9)
_cell_measurement_reflns_used    20281
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3270
_cell_measurement_theta_min      4.0150
_cell_volume                     1919.88(3)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22804
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         3.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    7.866
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_description       prism
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0166
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0293P)²+1.5219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0442
_refine_ls_wR_factor_ref         0.0443
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                3270
_reflns_number_total             3289
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0280_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               8105428
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.410
_shelx_estimated_absorpt_t_max   0.734
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.71041(2) 1.07282(6) 0.49566(3) 0.02286(10) Uani 1 1 d . . . . .
O1 O 0.500000 0.6195(6) 0.500000 0.0243(8) Uani 1 2 d S T P . .
C1 C 0.65770(10) 0.8905(6) 0.5020(3) 0.0171(7) Uani 1 1 d . . . . .
C2 C 0.66291(11) 0.6783(6) 0.5555(3) 0.0190(7) Uani 1 1 d . . . . .
H2 H 0.692322 0.620597 0.586411 0.023 Uiso 1 1 calc R U . . .
C3 C 0.62408(10) 0.5515(6) 0.5630(3) 0.0179(6) Uani 1 1 d . . . . .
H3 H 0.627095 0.405373 0.599724 0.021 Uiso 1 1 calc R U . . .
C4 C 0.58078(11) 0.6342(6) 0.5177(3) 0.0172(7) Uani 1 1 d . . . . .
C5 C 0.57695(11) 0.8488(6) 0.4634(3) 0.0179(7) Uani 1 1 d . . . . .
H5 H 0.547658 0.907569 0.432146 0.021 Uiso 1 1 calc R U . . .
C6 C 0.61544(10) 0.9773(6) 0.4546(3) 0.0180(7) Uani 1 1 d . . . . .
H6 H 0.612751 1.122309 0.416662 0.022 Uiso 1 1 calc R U . . .
C7 C 0.53983(10) 0.4892(6) 0.5253(3) 0.0188(7) Uani 1 1 d . . . . .
H7A H 0.538544 0.362960 0.465956 0.023 Uiso 1 1 calc R U . . .
H7B H 0.542269 0.423023 0.607969 0.023 Uiso 1 1 calc R U . . .
Br2 Br 0.52995(2) -0.04917(6) 0.79106(3) 0.02331(10) Uani 1 1 d . . . . .
Br3 Br 0.94938(2) -0.07311(5) 0.80258(3) 0.02156(9) Uani 1 1 d . . . . .
O2 O 0.74410(7) 0.3942(4) 0.8522(2) 0.0202(5) Uani 1 1 d . . . . .
C8 C 0.58424(10) 0.1270(6) 0.8185(3) 0.0167(7) Uani 1 1 d . . . . .
C9 C 0.58410(10) 0.3387(6) 0.8726(3) 0.0173(6) Uani 1 1 d . . . . .
H9 H 0.556937 0.398759 0.894875 0.021 Uiso 1 1 calc R U . . .
C10 C 0.62434(10) 0.4612(6) 0.8936(3) 0.0170(6) Uani 1 1 d . . . . .
H10 H 0.624690 0.606480 0.930955 0.020 Uiso 1 1 calc R U . . .
C11 C 0.66434(11) 0.3752(5) 0.8607(3) 0.0157(6) Uani 1 1 d . . . . .
C12 C 0.66356(11) 0.1620(6) 0.8063(3) 0.0163(6) Uani 1 1 d . . . . .
H12 H 0.690670 0.101474 0.783930 0.020 Uiso 1 1 calc R U . . .
C13 C 0.62348(10) 0.0368(6) 0.7844(3) 0.0167(6) Uani 1 1 d . . . . .
H13 H 0.622936 -0.108207 0.746686 0.020 Uiso 1 1 calc R U . . .
C14 C 0.70685(11) 0.5178(6) 0.8814(3) 0.0193(7) Uani 1 1 d . . . . .
H14A H 0.702225 0.655973 0.830156 0.023 Uiso 1 1 calc R U . . .
H14B H 0.713253 0.565810 0.967851 0.023 Uiso 1 1 calc R U . . .
C15 C 0.78371(10) 0.5299(6) 0.8572(3) 0.0195(7) Uani 1 1 d . . . . .
H15A H 0.790202 0.607906 0.937059 0.023 Uiso 1 1 calc R U . . .
H15B H 0.778801 0.647046 0.792493 0.023 Uiso 1 1 calc R U . . .
C16 C 0.82363(10) 0.3810(5) 0.8398(3) 0.0155(7) Uani 1 1 d . . . . .
C17 C 0.81764(11) 0.1725(6) 0.7811(3) 0.0172(6) Uani 1 1 d . . . . .
H17 H 0.787784 0.121274 0.749548 0.021 Uiso 1 1 calc R U . . .
C18 C 0.85501(10) 0.0381(6) 0.7680(3) 0.0177(6) Uani 1 1 d . . . . .
H18 H 0.850948 -0.105026 0.728238 0.021 Uiso 1 1 calc R U . . .
C19 C 0.89837(10) 0.1166(6) 0.8141(3) 0.0170(7) Uani 1 1 d . . . . .
C20 C 0.90519(10) 0.3266(6) 0.8701(3) 0.0178(6) Uani 1 1 d . . . . .
H20 H 0.935093 0.380005 0.899128 0.021 Uiso 1 1 calc R U . . .
C21 C 0.86749(10) 0.4572(6) 0.8828(3) 0.0180(6) Uani 1 1 d . . . . .
H21 H 0.871680 0.601102 0.921646 0.022 Uiso 1 1 calc R U . . .
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 O1 C7 113.6(4) 2_656 .
C6 C1 C2 122.1(3) . .
C6 C1 Br1 118.7(3) . .
C2 C1 Br1 119.2(2) . .
C1 C2 C3 118.3(3) . .
C1 C2 H2 120.8 . .
C3 C2 H2 120.8 . .
C2 C3 C4 121.3(3) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C3 C4 C5 118.6(3) . .
C3 C4 C7 119.5(3) . .
C5 C4 C7 121.8(3) . .
C6 C5 C4 120.8(3) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C1 C6 C5 118.8(3) . .
C1 C6 H6 120.6 . .
C5 C6 H6 120.6 . .
O1 C7 C4 110.2(3) . .
O1 C7 H7A 109.6 . .
C4 C7 H7A 109.6 . .
O1 C7 H7B 109.6 . .
C4 C7 H7B 109.6 . .
H7A C7 H7B 108.1 . .
C14 O2 C15 112.3(2) . .
C13 C8 C9 121.6(3) . .
C13 C8 Br2 118.5(3) . .
C9 C8 Br2 120.0(2) . .
C10 C9 C8 118.7(3) . .
C10 C9 H9 120.7 . .
C8 C9 H9 120.7 . .
C9 C10 C11 121.1(3) . .
C9 C10 H10 119.4 . .
C11 C10 H10 119.4 . .
C10 C11 C12 119.1(3) . .
C10 C11 C14 119.2(3) . .
C12 C11 C14 121.7(3) . .
C13 C12 C11 120.6(3) . .
C13 C12 H12 119.7 . .
C11 C12 H12 119.7 . .
C8 C13 C12 119.0(3) . .
C8 C13 H13 120.5 . .
C12 C13 H13 120.5 . .
O2 C14 C11 110.5(3) . .
O2 C14 H14A 109.6 . .
C11 C14 H14A 109.6 . .
O2 C14 H14B 109.6 . .
C11 C14 H14B 109.6 . .
H14A C14 H14B 108.1 . .
O2 C15 C16 109.4(3) . .
O2 C15 H15A 109.8 . .
C16 C15 H15A 109.8 . .
O2 C15 H15B 109.8 . .
C16 C15 H15B 109.8 . .
H15A C15 H15B 108.2 . .
C17 C16 C21 119.3(3) . .
C17 C16 C15 121.9(3) . .
C21 C16 C15 118.8(3) . .
C16 C17 C18 120.5(3) . .
C16 C17 H17 119.8 . .
C18 C17 H17 119.8 . .
C19 C18 C17 118.9(3) . .
C19 C18 H18 120.6 . .
C17 C18 H18 120.6 . .
C20 C19 C18 121.6(3) . .
C20 C19 Br3 119.5(2) . .
C18 C19 Br3 118.9(3) . .
C19 C20 C21 118.6(3) . .
C19 C20 H20 120.7 . .
C21 C20 H20 120.7 . .
C20 C21 C16 121.1(3) . .
C20 C21 H21 119.5 . .
C16 C21 H21 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.910(3) .
O1 C7 1.401(4) 2_656
O1 C7 1.402(4) .
C1 C6 1.381(4) .
C1 C2 1.381(5) .
C2 C3 1.389(5) .
C2 H2 0.9500 .
C3 C4 1.393(4) .
C3 H3 0.9500 .
C4 C5 1.397(5) .
C4 C7 1.500(4) .
C5 C6 1.388(5) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
Br2 C8 1.902(3) .
Br3 C19 1.904(3) .
O2 C14 1.406(4) .
O2 C15 1.417(4) .
C8 C13 1.388(4) .
C8 C9 1.384(5) .
C9 C10 1.385(5) .
C9 H9 0.9500 .
C10 C11 1.394(4) .
C10 H10 0.9500 .
C11 C12 1.392(5) .
C11 C14 1.504(4) .
C12 C13 1.389(5) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.513(4) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.388(5) .
C16 C21 1.390(4) .
C17 C18 1.391(5) .
C17 H17 0.9500 .
C18 C19 1.388(4) .
C18 H18 0.9500 .
C19 C20 1.384(5) .
C20 C21 1.385(5) .
C20 H20 0.9500 .
C21 H21 0.9500 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.0(4) . . . .
Br1 C1 C2 C3 177.8(2) . . . .
C1 C2 C3 C4 0.2(4) . . . .
C2 C3 C4 C5 0.3(5) . . . .
C2 C3 C4 C7 178.6(3) . . . .
C3 C4 C5 C6 0.0(4) . . . .
C7 C4 C5 C6 -178.3(3) . . . .
C2 C1 C6 C5 1.4(5) . . . .
Br1 C1 C6 C5 -177.5(2) . . . .
C4 C5 C6 C1 -0.9(5) . . . .
C7 O1 C7 C4 164.7(3) 2_656 . . .
C3 C4 C7 O1 167.2(3) . . . .
C5 C4 C7 O1 -14.6(4) . . . .
C13 C8 C9 C10 -0.5(5) . . . .
Br2 C8 C9 C10 178.8(2) . . . .
C8 C9 C10 C11 0.3(5) . . . .
C9 C10 C11 C12 -0.2(4) . . . .
C9 C10 C11 C14 177.9(3) . . . .
C10 C11 C12 C13 0.3(4) . . . .
C14 C11 C12 C13 -177.8(3) . . . .
C9 C8 C13 C12 0.6(5) . . . .
Br2 C8 C13 C12 -178.7(2) . . . .
C11 C12 C13 C8 -0.5(5) . . . .
C15 O2 C14 C11 173.4(2) . . . .
C10 C11 C14 O2 175.0(3) . . . .
C12 C11 C14 O2 -6.9(4) . . . .
C14 O2 C15 C16 173.3(2) . . . .
O2 C15 C16 C17 23.2(4) . . . .
O2 C15 C16 C21 -157.5(3) . . . .
C21 C16 C17 C18 1.6(4) . . . .
C15 C16 C17 C18 -179.1(3) . . . .
C16 C17 C18 C19 -0.4(5) . . . .
C17 C18 C19 C20 -1.4(5) . . . .
C17 C18 C19 Br3 177.3(2) . . . .
C18 C19 C20 C21 1.8(4) . . . .
Br3 C19 C20 C21 -176.9(2) . . . .
C19 C20 C21 C16 -0.5(4) . . . .
C17 C16 C21 C20 -1.2(4) . . . .
C15 C16 C21 C20 179.5(3) . . . .
