#------------------------------------------------------------------------------
#$Date: 2023-08-31 05:02:10 +0300 (Thu, 31 Aug 2023) $
#$Revision: 285925 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022850.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_2022850
loop_
_publ_author_name
'Akkurt, Mehmet'
'Naghiyev, Farid N.'
'Khrustalev, Victor N.'
'Asadov, Khammed A.'
'Khalilov, Ali N.'
'Bhattarai, Ajaya'
'Mamedov, İbrahim G.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (2E)-1-(4-bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one
;
_journal_coeditor_code           TX2073
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              847
_journal_page_last               851
_journal_paper_doi               10.1107/S2056989023007387
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C16 H13 Br O'
_chemical_formula_moiety         'C16 H13 Br O'
_chemical_formula_sum            'C16 H13 Br O'
_chemical_formula_weight         301.17
_chemical_name_systematic
;
(2E)-1-(4-Bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.942
_cell_length_b                   11.5915(2)
_cell_length_c                   28.0387(4)
_cell_measurement_reflns_used    12560
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.868
_cell_measurement_theta_min      3.795
_cell_volume                     1281.19(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14537
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.111
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.231
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.251
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2022)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.418
_refine_ls_abs_structure_details
;
Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.53(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0215
_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)+(0.0121P)²+1.3924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0524
_reflns_number_gt                2627
_reflns_number_total             2657
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2073sup1.cif
_cod_data_source_block           I
_cod_database_code               2022850
_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   0.319
_shelx_estimated_absorpt_t_max   0.756
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6338(7) 0.6732(2) 0.28488(10) 0.0156(6) Uani d 1 . .
C C2 0.5186(8) 0.5849(3) 0.31975(11) 0.0179(6) Uani d 1 . .
H H2 0.576288 0.506108 0.315259 0.021 Uiso calc 1 . .
C C3 0.3333(8) 0.6169(3) 0.35751(10) 0.0167(6) Uani d 1 . .
H H3 0.272264 0.696111 0.359037 0.020 Uiso calc 1 . .
C C4 0.2138(8) 0.5441(3) 0.39673(9) 0.0162(5) Uani d 1 . .
C C5 0.0419(8) 0.5941(3) 0.43586(11) 0.0199(6) Uani d 1 . .
C C6 -0.0614(9) 0.5231(3) 0.47322(11) 0.0243(7) Uani d 1 . .
H H6 -0.174643 0.556148 0.499821 0.029 Uiso calc 1 . .
C C7 -0.0025(9) 0.4050(3) 0.47241(12) 0.0260(8) Uani d 1 . .
H H7 -0.075592 0.358302 0.498276 0.031 Uiso calc 1 . .
C C8 0.1629(10) 0.3552(3) 0.43386(11) 0.0244(7) Uani d 1 . .
H H8 0.202810 0.274348 0.433117 0.029 Uiso calc 1 . .
C C9 0.2691(8) 0.4245(3) 0.39655(10) 0.0200(6) Uani d 1 . .
H H9 0.382068 0.390249 0.370170 0.024 Uiso calc 1 . .
C C10 -0.0317(9) 0.7216(3) 0.43748(12) 0.0225(7) Uani d 1 . .
H H10A -0.155611 0.739898 0.466828 0.034 Uiso calc 1 . .
H H10B -0.169550 0.743225 0.409802 0.034 Uiso calc 1 . .
H H10C 0.182210 0.764687 0.436880 0.034 Uiso calc 1 . .
C C11 0.7811(8) 0.6341(2) 0.23829(10) 0.0151(5) Uani d 1 . .
C C12 0.7419(7) 0.5219(2) 0.22102(9) 0.0170(6) Uani d 1 . .
H H12 0.629276 0.465770 0.239962 0.020 Uiso calc 1 . .
C C13 0.8664(8) 0.4916(2) 0.17629(11) 0.0180(6) Uani d 1 . .
H H13 0.839832 0.415359 0.164401 0.022 Uiso calc 1 . .
C C14 1.0295(8) 0.5750(3) 0.14959(10) 0.0170(6) Uani d 1 . .
C C15 1.0768(8) 0.6869(3) 0.16597(11) 0.0178(6) Uani d 1 . .
H H15 1.193503 0.742210 0.147111 0.021 Uiso calc 1 . .
C C16 0.9500(8) 0.7159(3) 0.21041(11) 0.0172(6) Uani d 1 . .
H H16 0.978056 0.792262 0.222085 0.021 Uiso calc 1 . .
Br Br1 1.19480(8) 0.53645(3) 0.08770(2) 0.02188(9) Uani d 1 . .
O O1 0.6109(6) 0.77583(19) 0.29371(8) 0.0242(5) 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 0.0181 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 121.1(3) ?
O1 C1 C11 . . 120.1(3) ?
C2 C1 C11 . . 118.9(3) ?
C3 C2 C1 . . 119.7(3) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 127.6(3) ?
C2 C3 H3 . . 116.2 ?
C4 C3 H3 . . 116.2 ?
C9 C4 C5 . . 118.8(3) ?
C9 C4 C3 . . 121.1(3) ?
C5 C4 C3 . . 120.1(3) ?
C6 C5 C4 . . 118.8(3) ?
C6 C5 C10 . . 120.0(3) ?
C4 C5 C10 . . 121.2(3) ?
C7 C6 C5 . . 121.4(3) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C6 C7 C8 . . 120.1(3) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C9 C8 C7 . . 119.3(3) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C8 C9 C4 . . 121.6(3) ?
C8 C9 H9 . . 119.2 ?
C4 C9 H9 . . 119.2 ?
C5 C10 H10A . . 109.5 ?
C5 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C5 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C16 . . 119.4(3) ?
C12 C11 C1 . . 122.8(3) ?
C16 C11 C1 . . 117.8(3) ?
C13 C12 C11 . . 120.6(3) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C14 C13 C12 . . 118.4(3) ?
C14 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C13 C14 C15 . . 122.5(3) ?
C13 C14 Br1 . . 119.2(2) ?
C15 C14 Br1 . . 118.3(2) ?
C16 C15 C14 . . 118.4(3) ?
C16 C15 H15 . . 120.8 ?
C14 C15 H15 . . 120.8 ?
C15 C16 C11 . . 120.7(3) ?
C15 C16 H16 . . 119.7 ?
C11 C16 H16 . . 119.7 ?
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
C1 O1 . 1.218(4) ?
C1 C2 . 1.487(4) ?
C1 C11 . 1.500(4) ?
C2 C3 . 1.339(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.464(4) ?
C3 H3 . 0.9500 ?
C4 C9 . 1.404(4) ?
C4 C5 . 1.414(4) ?
C5 C6 . 1.393(5) ?
C5 C10 . 1.507(5) ?
C6 C7 . 1.388(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.389(5) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.384(4) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.396(4) ?
C11 C16 . 1.398(4) ?
C12 C13 . 1.392(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.381(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.389(4) ?
C14 Br1 . 1.907(3) ?
C15 C16 . 1.384(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
C3 H3 O1 . 0.95 2.45 2.791(4) 101 no
C12 H12 O1 3_645 0.95 2.58 3.200(3) 124 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 C1 C2 C3 . . . . 12.0(5) ?
C11 C1 C2 C3 . . . . -168.2(3) ?
C1 C2 C3 C4 . . . . -176.3(3) ?
C2 C3 C4 C9 . . . . -4.4(5) ?
C2 C3 C4 C5 . . . . 175.1(3) ?
C9 C4 C5 C6 . . . . 1.1(5) ?
C3 C4 C5 C6 . . . . -178.4(3) ?
C9 C4 C5 C10 . . . . -178.6(3) ?
C3 C4 C5 C10 . . . . 1.9(5) ?
C4 C5 C6 C7 . . . . -0.8(5) ?
C10 C5 C6 C7 . . . . 178.9(3) ?
C5 C6 C7 C8 . . . . 0.1(6) ?
C6 C7 C8 C9 . . . . 0.3(5) ?
C7 C8 C9 C4 . . . . 0.1(5) ?
C5 C4 C9 C8 . . . . -0.7(5) ?
C3 C4 C9 C8 . . . . 178.7(3) ?
O1 C1 C11 C12 . . . . -164.3(3) ?
C2 C1 C11 C12 . . . . 15.9(4) ?
O1 C1 C11 C16 . . . . 12.6(4) ?
C2 C1 C11 C16 . . . . -167.2(3) ?
C16 C11 C12 C13 . . . . -0.6(4) ?
C1 C11 C12 C13 . . . . 176.2(3) ?
C11 C12 C13 C14 . . . . 0.1(4) ?
C12 C13 C14 C15 . . . . 0.8(5) ?
C12 C13 C14 Br1 . . . . -178.8(2) ?
C13 C14 C15 C16 . . . . -1.1(5) ?
Br1 C14 C15 C16 . . . . 178.5(2) ?
C14 C15 C16 C11 . . . . 0.6(5) ?
C12 C11 C16 C15 . . . . 0.3(5) ?
C1 C11 C16 C15 . . . . -176.7(3) ?

_cod_database_fobs_code 2022850
