#------------------------------------------------------------------------------
#$Date: 2019-08-30 10:11:37 +0300 (Fri, 30 Aug 2019) $
#$Revision: 217870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/30/2243071.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_2243071
loop_
_publ_author_name
'Bindya, S.'
'Chidan Kumar, C. S.'
'Naveen, S.'
'Siddaraju, B. P.'
'Quah, Ching Kheng'
'Md. Abu Raihan'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of a bromochalcone:
 (E)-1-(3-bromophenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one
;
_journal_coeditor_code           QM2132
_journal_issue                   2
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              264
_journal_page_last               267
_journal_paper_doi               10.1107/S205698901900104X
_journal_volume                  75
_journal_year                    2019
_chemical_compound_source        'see text'
_chemical_formula_iupac          'C15 H9 Br Cl2 O'
_chemical_formula_moiety         'C15 H9 Br Cl2 O'
_chemical_formula_sum            'C15 H9 Br Cl2 O'
_chemical_formula_weight         356.02
_chemical_name_systematic
;
(E)-1-(3-bromophenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 92.736(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9834(7)
_cell_length_b                   13.471(2)
_cell_length_c                   25.661(4)
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    294
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      1.59
_cell_volume                     1375.4(4)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      294
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10857
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.82
_diffrn_reflns_theta_max         27.82
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    3.364
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_correction_T_min  0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.333
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0691P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2260
_reflns_number_total             3242
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2132sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243071
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.05103(10) 0.56559(3) 0.063840(10) 0.0533(2) Uani d . 1.000 . .
Cl Cl1 1.1724(3) 0.85319(6) 0.33444(4) 0.0585(3) Uani d . 1.000 . .
Cl Cl2 1.1077(3) 0.48639(7) 0.42380(4) 0.0629(4) Uani d . 1.000 . .
O O1 0.6757(10) 0.5127(2) 0.25232(11) 0.0795(13) Uani d . 1.000 . .
C C1 1.2349(8) 0.7699(2) 0.38553(13) 0.0400(10) Uani d . 1.000 . .
C C2 1.3925(9) 0.8068(3) 0.43034(14) 0.0482(11) Uani d . 1.000 . .
C C3 1.4602(10) 0.7456(3) 0.47251(15) 0.0551(12) Uani d . 1.000 . .
C C4 1.3682(9) 0.6477(3) 0.46994(13) 0.0489(11) Uani d . 1.000 . .
C C5 1.2137(9) 0.6115(2) 0.42448(13) 0.0411(10) Uani d . 1.000 . .
C C6 1.1375(8) 0.6695(2) 0.38034(12) 0.0344(9) Uani d . 1.000 . .
C C7 0.9826(9) 0.6237(2) 0.33364(13) 0.0423(11) Uani d . 1.000 . .
C C8 0.8005(9) 0.6605(3) 0.29567(13) 0.0464(11) Uani d . 1.000 . .
C C9 0.6625(9) 0.6020(3) 0.25107(13) 0.0433(11) Uani d . 1.000 . .
C C10 0.5026(8) 0.6542(2) 0.20468(12) 0.0386(10) Uani d . 1.000 . .
C C11 0.3737(8) 0.5979(2) 0.16350(12) 0.0386(10) Uani d . 1.000 . .
C C12 0.2288(8) 0.6434(2) 0.12041(12) 0.0377(10) Uani d . 1.000 . .
C C13 0.2083(10) 0.7454(3) 0.11687(14) 0.0512(12) Uani d . 1.000 . .
C C14 0.3403(11) 0.8019(3) 0.15749(15) 0.0572(14) Uani d . 1.000 . .
C C15 0.4858(10) 0.7575(3) 0.20135(15) 0.0494(11) Uani d . 1.000 . .
H H2A 1.45350 0.87340 0.43210 0.0580 Uiso c R 1.000 . .
H H3A 1.56810 0.77070 0.50260 0.0660 Uiso c R 1.000 . .
H H4A 1.40930 0.60610 0.49850 0.0590 Uiso c R 1.000 . .
H H7A 1.02250 0.55590 0.33080 0.0510 Uiso c R 1.000 . .
H H8A 0.75310 0.72810 0.29640 0.0560 Uiso c R 1.000 . .
H H11A 0.38530 0.52900 0.16500 0.0460 Uiso c R 1.000 . .
H H13A 0.10710 0.77540 0.08750 0.0620 Uiso c R 1.000 . .
H H14A 0.33120 0.87080 0.15540 0.0680 Uiso c R 1.000 . .
H H15A 0.57290 0.79640 0.22870 0.0590 Uiso c R 1.000 . .
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'
Cl Cl 0.1484 0.1585 ' 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 C1 C2 . . . 116.2(2) no
Cl1 C1 C6 . . . 121.3(2) no
C2 C1 C6 . . . 122.5(3) no
C1 C2 C3 . . . 120.3(4) no
C2 C3 C4 . . . 119.8(4) no
C3 C4 C5 . . . 119.2(3) no
Cl2 C5 C4 . . . 116.7(3) no
Cl2 C5 C6 . . . 119.4(2) no
C4 C5 C6 . . . 123.9(3) no
C1 C6 C5 . . . 114.3(3) no
C1 C6 C7 . . . 125.9(3) no
C5 C6 C7 . . . 119.8(3) no
C6 C7 C8 . . . 131.4(3) no
C7 C8 C9 . . . 123.9(4) no
O1 C9 C8 . . . 119.9(3) no
O1 C9 C10 . . . 120.4(3) no
C8 C9 C10 . . . 119.6(3) no
C9 C10 C11 . . . 118.6(3) no
C9 C10 C15 . . . 122.3(3) no
C11 C10 C15 . . . 119.1(3) no
C10 C11 C12 . . . 120.0(3) no
Br1 C12 C11 . . . 119.9(2) no
Br1 C12 C13 . . . 118.7(2) no
C11 C12 C13 . . . 121.4(3) no
C12 C13 C14 . . . 118.8(3) no
C13 C14 C15 . . . 120.7(4) no
C10 C15 C14 . . . 120.0(4) no
C1 C2 H2A . . . 120.00 no
C3 C2 H2A . . . 120.00 no
C2 C3 H3A . . . 120.00 no
C4 C3 H3A . . . 120.00 no
C3 C4 H4A . . . 120.00 no
C5 C4 H4A . . . 120.00 no
C6 C7 H7A . . . 114.00 no
C8 C7 H7A . . . 114.00 no
C7 C8 H8A . . . 118.00 no
C9 C8 H8A . . . 118.00 no
C10 C11 H11A . . . 120.00 no
C12 C11 H11A . . . 120.00 no
C12 C13 H13A . . . 121.00 no
C14 C13 H13A . . . 121.00 no
C13 C14 H14A . . . 120.00 no
C15 C14 H14A . . . 120.00 no
C10 C15 H15A . . . 120.00 no
C14 C15 H15A . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C12 . . 1.900(3) no
Cl1 C1 . . 1.735(3) no
Cl2 C5 . . 1.737(3) no
O1 C9 . . 1.205(5) no
C1 C2 . . 1.376(5) no
C1 C6 . . 1.412(4) no
C2 C3 . . 1.377(5) no
C3 C4 . . 1.370(6) no
C4 C5 . . 1.382(5) no
C5 C6 . . 1.397(4) no
C6 C7 . . 1.458(4) no
C7 C8 . . 1.286(5) no
C8 C9 . . 1.474(5) no
C9 C10 . . 1.498(5) no
C10 C11 . . 1.380(4) no
C10 C15 . . 1.396(5) no
C11 C12 . . 1.368(4) no
C12 C13 . . 1.379(5) no
C13 C14 . . 1.375(5) no
C14 C15 . . 1.378(6) no
C2 H2A . . 0.9300 no
C3 H3A . . 0.9300 no
C4 H4A . . 0.9300 no
C7 H7A . . 0.9300 no
C8 H8A . . 0.9300 no
C11 H11A . . 0.9300 no
C13 H13A . . 0.9300 no
C14 H14A . . 0.9300 no
C15 H15A . . 0.9300 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
C8 H8A Cl1 . 0.93 2.54 3.128(4) 122 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
Cl1 C1 C2 C3 . . . . -178.4(3) no
C6 C1 C2 C3 . . . . -0.3(5) no
Cl1 C1 C6 C5 . . . . 178.3(2) no
Cl1 C1 C6 C7 . . . . 0.8(5) no
C2 C1 C6 C5 . . . . 0.2(5) no
C2 C1 C6 C7 . . . . -177.3(3) no
C1 C2 C3 C4 . . . . -0.4(6) no
C2 C3 C4 C5 . . . . 1.2(6) no
C3 C4 C5 Cl2 . . . . 179.4(3) no
C3 C4 C5 C6 . . . . -1.3(6) no
Cl2 C5 C6 C1 . . . . 179.9(3) no
Cl2 C5 C6 C7 . . . . -2.4(4) no
C4 C5 C6 C1 . . . . 0.6(5) no
C4 C5 C6 C7 . . . . 178.3(3) no
C1 C6 C7 C8 . . . . -26.8(6) no
C5 C6 C7 C8 . . . . 155.8(4) no
C6 C7 C8 C9 . . . . -179.8(3) no
C7 C8 C9 O1 . . . . 10.9(6) no
C7 C8 C9 C10 . . . . -169.8(3) no
O1 C9 C10 C11 . . . . -0.5(5) no
O1 C9 C10 C15 . . . . -179.2(4) no
C8 C9 C10 C11 . . . . -179.7(3) no
C8 C9 C10 C15 . . . . 1.6(5) no
C9 C10 C11 C12 . . . . -179.4(3) no
C15 C10 C11 C12 . . . . -0.7(5) no
C9 C10 C15 C14 . . . . 179.1(4) no
C11 C10 C15 C14 . . . . 0.4(5) no
C10 C11 C12 Br1 . . . . -179.9(2) no
C10 C11 C12 C13 . . . . 0.2(5) no
Br1 C12 C13 C14 . . . . -179.2(3) no
C11 C12 C13 C14 . . . . 0.7(5) no
C12 C13 C14 C15 . . . . -1.0(6) no
C13 C14 C15 C10 . . . . 0.5(6) no

_cod_database_fobs_code 2243071
