#------------------------------------------------------------------------------
#$Date: 2020-08-14 07:45:47 +0300 (Fri, 14 Aug 2020) $
#$Revision: 255315 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022235.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_2022235
loop_
_publ_author_name
'Cong, Nguyen Tien'
'Trang, Huynh Thi Xuan'
'Dung, Pham Duc'
'Phuong, Tran Hoang'
'Trung, Vu Quoc'
'Dat, Nguyen Dang'
'Anh, Dang Thi Tuyet'
'Tuyen, Nguyen Van'
'Van Meervelt, Luc'
_publ_section_title
;
 Synthesis, structure and in vitro cytotoxicity testing of some
 2-aroylbenzofuran-3-ols
;
_journal_coeditor_code           SK3753
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620011018
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C15 H8 Br2 O3'
_chemical_formula_moiety         'C15 H8 Br2 O3'
_chemical_formula_sum            'C15 H8 Br2 O3'
_chemical_formula_weight         396.03
_chemical_name_systematic
;
(5-Bromo-3-hydroxybenzofuran-2-yl)(4-bromophenyl)methanone
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                92.230(5)
_cell_angle_beta                 103.091(5)
_cell_angle_gamma                101.219(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0725(4)
_cell_length_b                   7.0884(5)
_cell_length_c                   14.6069(8)
_cell_measurement_reflns_used    3969
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.0150
_cell_measurement_theta_min      2.8510
_cell_volume                     696.98(8)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku OD SuperNova Single source diffractometer with an Eos detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14183
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         2.874
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0462
_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)+(0.0415P)²+0.4345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                1867
_reflns_number_total             2840
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3753sup1.cif
_cod_data_source_block           4c
_cod_database_code               2022235
_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   0.235
_shelx_estimated_absorpt_t_max   0.760
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2698(4) 0.5503(4) 0.38600(19) 0.0488(7) Uani d 1 . .
C C2 0.2236(6) 0.3699(6) 0.4205(3) 0.0451(10) Uani d 1 . .
C C3 0.1893(6) 0.2269(6) 0.3496(3) 0.0492(10) Uani d 1 . .
C C4 0.2133(6) 0.3147(6) 0.2657(3) 0.0467(10) Uani d 1 . .
C C5 0.1950(6) 0.2465(7) 0.1721(3) 0.0538(11) Uani d 1 . .
H H5 0.162112 0.115376 0.152601 0.065 Uiso calc 1 . .
C C6 0.2283(6) 0.3842(8) 0.1110(3) 0.0603(13) Uani d 1 . .
C C7 0.2745(7) 0.5815(8) 0.1380(3) 0.0644(13) Uani d 1 . .
H H7 0.294088 0.668302 0.093245 0.077 Uiso calc 1 . .
C C8 0.2919(7) 0.6517(7) 0.2302(3) 0.0583(12) Uani d 1 . .
H H8 0.322333 0.783073 0.249141 0.070 Uiso calc 1 . .
C C9 0.2605(6) 0.5113(6) 0.2925(3) 0.0470(10) Uani d 1 . .
C C10 0.2117(6) 0.3412(6) 0.5157(3) 0.0471(10) Uani d 1 . .
O O11 0.1679(5) 0.1689(4) 0.5325(2) 0.0672(9) Uani d 1 . .
C C12 0.2445(5) 0.4957(6) 0.5920(3) 0.0432(10) Uani d 1 . .
C C13 0.2243(6) 0.4393(7) 0.6802(3) 0.0528(11) Uani d 1 . .
H H13 0.190559 0.308580 0.688378 0.063 Uiso calc 1 . .
C C14 0.2529(6) 0.5720(7) 0.7550(3) 0.0562(12) Uani d 1 . .
H H14 0.239823 0.532483 0.813584 0.067 Uiso calc 1 . .
C C15 0.3015(6) 0.7652(7) 0.7422(3) 0.0516(11) Uani d 1 . .
C C16 0.3218(6) 0.8272(7) 0.6564(3) 0.0538(11) Uani d 1 . .
H H16 0.354165 0.958359 0.648961 0.065 Uiso calc 1 . .
C C17 0.2934(6) 0.6921(6) 0.5815(3) 0.0485(10) Uani d 1 . .
H H17 0.307233 0.732746 0.523116 0.058 Uiso calc 1 . .
Br Br18 0.34142(8) 0.94907(8) 0.84645(4) 0.0757(2) Uani d 1 . .
O O19 0.1385(5) 0.0365(5) 0.3552(3) 0.0671(9) Uani d 1 . .
Br Br20 0.20857(10) 0.30111(10) -0.01643(4) 0.0906(3) Uani d 1 . .
H H19 0.127(9) 0.030(8) 0.411(4) 0.10(2) Uiso 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'
H H 0.0000 0.0000 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C2 . . 105.3(3) ?
O1 C2 C10 . . 124.7(4) ?
C3 C2 O1 . . 109.8(3) ?
C3 C2 C10 . . 125.5(4) ?
C2 C3 C4 . . 108.2(4) ?
O19 C3 C2 . . 127.2(4) ?
O19 C3 C4 . . 124.6(4) ?
C5 C4 C3 . . 135.0(4) ?
C9 C4 C3 . . 104.4(4) ?
C9 C4 C5 . . 120.6(4) ?
C6 C5 C4 . . 116.2(4) ?
C5 C6 C7 . . 123.1(4) ?
C5 C6 Br20 . . 118.2(4) ?
C7 C6 Br20 . . 118.7(4) ?
C8 C7 C6 . . 121.5(4) ?
C7 C8 C9 . . 115.2(5) ?
O1 C9 C4 . . 112.3(3) ?
O1 C9 C8 . . 124.3(4) ?
C4 C9 C8 . . 123.4(4) ?
C2 C10 C12 . . 125.6(4) ?
O11 C10 C2 . . 114.9(4) ?
O11 C10 C12 . . 119.5(4) ?
C13 C12 C10 . . 117.3(4) ?
C17 C12 C10 . . 124.5(3) ?
C17 C12 C13 . . 118.2(4) ?
C14 C13 C12 . . 121.3(4) ?
C13 C14 C15 . . 119.0(4) ?
C14 C15 Br18 . . 118.7(3) ?
C16 C15 C14 . . 121.6(4) ?
C16 C15 Br18 . . 119.6(3) ?
C15 C16 C17 . . 119.0(4) ?
C16 C17 C12 . . 120.8(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.399(5) ?
O1 C9 . 1.368(5) ?
C2 C3 . 1.367(6) ?
C2 C10 . 1.432(5) ?
C3 C4 . 1.425(5) ?
C3 O19 . 1.338(5) ?
C4 C5 . 1.400(6) ?
C4 C9 . 1.387(6) ?
C5 C6 . 1.370(6) ?
C6 C7 . 1.393(7) ?
C6 Br20 . 1.896(4) ?
C7 C8 . 1.387(6) ?
C8 C9 . 1.394(6) ?
C10 O11 . 1.248(5) ?
C10 C12 . 1.478(6) ?
C12 C13 . 1.394(5) ?
C12 C17 . 1.391(6) ?
C13 C14 . 1.365(6) ?
C14 C15 . 1.376(6) ?
C15 C16 . 1.372(6) ?
C15 Br18 . 1.899(4) ?
C16 C17 . 1.379(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O19 H19 O11 1_555 1_555 1_555 0.84(6) 1.93(6) 2.669(5) 146(5) yes
C17 H17 O1 1_555 1_555 1_555 0.93 2.28 2.948(5) 129 yes
O19 H19 O11 1_555 1_555 2_556 0.84(6) 2.60(6) 3.174(5) 127 yes
C14 H14 Br20 1_555 1_555 1_556 0.93 3.05 3.959(5) 165 yes
C16 H16 O11 1_555 1_555 1_565 0.93 2.61 3.287(6) 130 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C2 C3 C4 . . . . 0.0(5) ?
O1 C2 C3 O19 . . . . -179.0(4) ?
O1 C2 C10 O11 . . . . 179.8(4) ?
O1 C2 C10 C12 . . . . 0.5(6) ?
C2 O1 C9 C4 . . . . -0.8(4) ?
C2 O1 C9 C8 . . . . 178.3(4) ?
C2 C3 C4 C5 . . . . -178.7(4) ?
C2 C3 C4 C9 . . . . -0.4(4) ?
C2 C10 C12 C13 . . . . 179.3(4) ?
C2 C10 C12 C17 . . . . -0.6(6) ?
C3 C2 C10 O11 . . . . 0.7(6) ?
C3 C2 C10 C12 . . . . -178.6(4) ?
C3 C4 C5 C6 . . . . 178.7(4) ?
C3 C4 C9 O1 . . . . 0.8(4) ?
C3 C4 C9 C8 . . . . -178.4(4) ?
C4 C5 C6 C7 . . . . -1.1(6) ?
C4 C5 C6 Br20 . . . . 179.3(3) ?
C5 C4 C9 O1 . . . . 179.4(3) ?
C5 C4 C9 C8 . . . . 0.2(6) ?
C5 C6 C7 C8 . . . . 0.7(7) ?
C6 C7 C8 C9 . . . . 0.2(7) ?
C7 C8 C9 O1 . . . . -179.7(4) ?
C7 C8 C9 C4 . . . . -0.6(6) ?
C9 O1 C2 C3 . . . . 0.5(4) ?
C9 O1 C2 C10 . . . . -178.7(4) ?
C9 C4 C5 C6 . . . . 0.6(6) ?
C10 C2 C3 C4 . . . . 179.2(4) ?
C10 C2 C3 O19 . . . . 0.2(7) ?
C10 C12 C13 C14 . . . . 179.6(4) ?
C10 C12 C17 C16 . . . . -179.9(4) ?
O11 C10 C12 C13 . . . . 0.0(6) ?
O11 C10 C12 C17 . . . . -179.9(4) ?
C12 C13 C14 C15 . . . . 0.4(6) ?
C13 C12 C17 C16 . . . . 0.2(6) ?
C13 C14 C15 C16 . . . . 0.0(6) ?
C13 C14 C15 Br18 . . . . -179.9(3) ?
C14 C15 C16 C17 . . . . -0.3(6) ?
C15 C16 C17 C12 . . . . 0.2(6) ?
C17 C12 C13 C14 . . . . -0.5(6) ?
Br18 C15 C16 C17 . . . . 179.7(3) ?
O19 C3 C4 C5 . . . . 0.3(7) ?
O19 C3 C4 C9 . . . . 178.6(4) ?
Br20 C6 C7 C8 . . . . -179.7(3) ?

_cod_database_fobs_code 2022235
