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#$Date: 2022-03-11 11:38:57 +0200 (Fri, 11 Mar 2022) $
#$Revision: 273647 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104736.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_8104736
loop_
_publ_author_name
'Usman, Rabia'
'Khan, Arshad'
'Refat, Moamen S.'
'Al-Hazmi, Ghaferah H.'
'He, Nongyue'
_publ_section_title
;
 Synthesis and crystal structure of
 (2E,2′E)-3,3′-(1,3-phenylene)bis(1-(3-bromophenyl)prop-2-en-1-one),
 C24H16Br2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              863
_journal_page_last               864
_journal_paper_doi               10.1515/ncrs-2021-0139
_journal_volume                  236
_journal_year                    2021
_chemical_formula_sum            'C24 H16 Br2 N0 O2'
_chemical_formula_weight         496.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.407(3)
_cell_length_b                   44.336(16)
_cell_length_c                   6.046(2)
_cell_measurement_reflns_used    982
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.15
_cell_measurement_theta_min      2.75
_cell_volume                     1985.5(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7399
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_min         1.837
_exptl_absorpt_coefficient_mu    4.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0287P)²+3.5919P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1315
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1183
_reflns_number_total             1779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0139_suppl.cif
_cod_data_source_block           a21106b
_cod_original_cell_volume        1985.6(13)
_cod_database_code               8104736
_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   0.494
_shelx_estimated_absorpt_t_max   0.685
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_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 0.33707(10) 0.02317(2) 0.33389(13) 0.0622(3) Uani 1 1 d . . . . .
O1 O 0.2911(8) 0.14332(10) 0.4304(8) 0.0741(17) Uani 1 1 d . . . . .
C1 C 0.3569(8) 0.05838(12) 0.1574(11) 0.0453(15) Uani 1 1 d . . . . .
C2 C 0.4218(10) 0.05592(15) -0.0586(12) 0.0562(18) Uani 1 1 d . . . . .
H2 H 0.4492 0.0371 -0.1185 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4440(10) 0.08155(16) -0.1802(12) 0.062(2) Uani 1 1 d . . . . .
H3 H 0.4919 0.0804 -0.3221 0.074 Uiso 1 1 calc R U . . .
C4 C 0.3962(10) 0.10920(14) -0.0943(11) 0.0521(18) Uani 1 1 d . . . . .
H4 H 0.4084 0.1264 -0.1809 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3299(9) 0.11171(13) 0.1196(11) 0.0474(16) Uani 1 1 d . . . . .
C6 C 0.3108(9) 0.08564(12) 0.2468(12) 0.0467(16) Uani 1 1 d . . . . .
H6 H 0.2672 0.0868 0.3908 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2874(10) 0.14117(13) 0.2288(13) 0.0519(18) Uani 1 1 d . . . . .
C8 C 0.2396(10) 0.16735(13) 0.0899(12) 0.0548(18) Uani 1 1 d . . . . .
H8 H 0.2185 0.1647 -0.0604 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2267(9) 0.19450(12) 0.1772(11) 0.0479(16) Uani 1 1 d . . . . .
H9 H 0.2527 0.1960 0.3273 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1760(9) 0.22249(12) 0.0655(11) 0.0452(15) Uani 1 1 d . . . . .
C11 C 0.0960(9) 0.22306(13) -0.1432(11) 0.0491(16) Uani 1 1 d . . . . .
H11 H 0.0694 0.2050 -0.2140 0.059 Uiso 1 1 calc R U . . .
C12 C 0.0554(13) 0.2500 -0.2467(17) 0.054(3) Uani 1 2 d S T P . .
H12 H 0.0010 0.2500 -0.3853 0.065 Uiso 1 2 calc R U P . .
C15 C 0.2110(12) 0.2500 0.1673(14) 0.041(2) Uani 1 2 d S T P . .
H15 H 0.2598 0.2500 0.3090 0.050 Uiso 1 2 calc R U P . .
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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 121.7(6) . .
C6 C1 Br1 119.0(5) . .
C2 C1 Br1 119.3(5) . .
C3 C2 C1 118.7(6) . .
C2 C3 C4 120.5(7) . .
C3 C4 C5 120.9(6) . .
C4 C5 C6 118.9(6) . .
C4 C5 C7 123.7(6) . .
C6 C5 C7 117.3(6) . .
C1 C6 C5 119.2(6) . .
O1 C7 C8 120.7(6) . .
O1 C7 C5 120.2(6) . .
C8 C7 C5 119.1(6) . .
C9 C8 C7 120.5(6) . .
C8 C9 C10 127.5(6) . .
C15 C10 C11 117.7(6) . .
C15 C10 C9 119.5(6) . .
C11 C10 C9 122.8(6) . .
C12 C11 C10 121.2(6) . .
C11 C12 C11 119.7(9) . 7_565
C10 C15 C10 122.6(8) 7_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.897(6) .
O1 C7 1.223(8) .
C1 C6 1.367(8) .
C1 C2 1.396(9) .
C2 C3 1.363(9) .
C3 C4 1.378(9) .
C4 C5 1.388(8) .
C5 C6 1.396(8) .
C5 C7 1.497(9) .
C7 C8 1.475(9) .
C8 C9 1.318(8) .
C9 C10 1.462(8) .
C10 C15 1.390(7) .
C10 C11 1.395(8) .
C11 C12 1.382(7) .
C12 C11 1.382(7) 7_565
C15 C10 1.390(7) 7_565
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 1.9(10) . . . .
Br1 C1 C2 C3 -176.7(5) . . . .
C1 C2 C3 C4 -2.7(11) . . . .
C2 C3 C4 C5 2.1(11) . . . .
C3 C4 C5 C6 -0.6(10) . . . .
C3 C4 C5 C7 175.6(7) . . . .
C2 C1 C6 C5 -0.4(10) . . . .
Br1 C1 C6 C5 178.2(5) . . . .
C4 C5 C6 C1 -0.3(10) . . . .
C7 C5 C6 C1 -176.7(6) . . . .
C4 C5 C7 O1 -154.4(7) . . . .
C6 C5 C7 O1 21.9(10) . . . .
C4 C5 C7 C8 26.2(10) . . . .
C6 C5 C7 C8 -157.6(6) . . . .
O1 C7 C8 C9 10.2(11) . . . .
C5 C7 C8 C9 -170.3(7) . . . .
C7 C8 C9 C10 -178.1(6) . . . .
C8 C9 C10 C15 -164.4(7) . . . .
C8 C9 C10 C11 14.4(11) . . . .
C15 C10 C11 C12 0.9(11) . . . .
C9 C10 C11 C12 -177.9(7) . . . .
C10 C11 C12 C11 0.6(14) . . . 7_565
C11 C10 C15 C10 -2.6(13) . . . 7_565
C9 C10 C15 C10 176.3(5) . . . 7_565
