#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226399.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_2226399
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Veena, K.'
'Narayana, B.'
'Yathirajan, H. S.'
_publ_section_title
;
 (2E)-1-(2-Bromophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           CV2728
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1661
_journal_paper_doi               10.1107/S160053681002218X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H13 Br O2'
_chemical_formula_moiety         'C16 H13 Br O2'
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_formula_weight         317.17
_chemical_name_systematic
;
(2E)-1-(2-Bromophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.671(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.7300(8)
_cell_length_b                   4.0061(3)
_cell_length_c                   13.0035(6)
_cell_measurement_reflns_used    1981
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      74.0528
_cell_measurement_theta_min      4.4661
_cell_volume                     651.68(7)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with Ruby (Gemini Cu) detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2117
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.12
_diffrn_reflns_theta_min         4.46
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    4.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisRed; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.651
_refine_ls_abs_structure_details 'Flack (1983), 133 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0336
_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)+(0.0718P)²+0.5775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                1621
_reflns_number_total             1641
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2728.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2226399
_cod_database_fobs_code          2226399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.38764(3) 0.18817(18) 0.46303(2) 0.01538(15) Uani d . 1 . .
O O1 0.2178(2) 0.2427(10) 0.1406(2) 0.0211(8) Uani d . 1 . .
O O2 0.8860(2) 0.2977(9) 0.1659(2) 0.0209(7) Uani d . 1 . .
C C1 0.2190(3) 0.4727(13) 0.3077(3) 0.0149(9) Uani d . 1 . .
C C2 0.2577(3) 0.4233(12) 0.4142(3) 0.0119(8) Uani d . 1 . .
C C3 0.2022(3) 0.5312(12) 0.4896(3) 0.0166(9) Uani d . 1 . .
H H3A 0.2299 0.4917 0.5616 0.020 Uiso calc R 1 . .
C C4 0.1060(3) 0.6971(19) 0.4599(3) 0.0223(8) Uani d . 1 . .
H H4A 0.0679 0.7740 0.5116 0.027 Uiso calc R 1 . .
C C5 0.0651(3) 0.7513(12) 0.3545(3) 0.0211(11) Uani d . 1 . .
H H5A -0.0008 0.8660 0.3342 0.025 Uiso calc R 1 . .
C C6 0.1203(3) 0.6385(14) 0.2797(3) 0.0187(10) Uani d . 1 . .
H H6A 0.0913 0.6732 0.2078 0.022 Uiso calc R 1 . .
C C7 0.2730(3) 0.3590(12) 0.2195(3) 0.0173(9) Uani d . 1 . .
C C8 0.3891(3) 0.4058(13) 0.2303(3) 0.0160(9) Uani d . 1 . .
H H8A 0.4255 0.5526 0.2824 0.019 Uiso calc R 1 . .
C C9 0.4441(3) 0.2431(12) 0.1673(3) 0.0161(10) Uani d . 1 . .
H H9A 0.4037 0.1037 0.1154 0.019 Uiso calc R 1 . .
C C10 0.5595(3) 0.2564(10) 0.1697(3) 0.0145(11) Uani d . 1 . .
C C11 0.5999(3) 0.1064(11) 0.0878(3) 0.0164(10) Uani d . 1 . .
H H11A 0.5519 -0.0064 0.0344 0.020 Uiso calc R 1 . .
C C12 0.7083(3) 0.1171(11) 0.0822(3) 0.0155(10) Uani d . 1 . .
H H12A 0.7334 0.0191 0.0248 0.019 Uiso calc R 1 . .
C C13 0.7787(3) 0.2733(11) 0.1619(3) 0.0156(10) Uani d . 1 . .
C C14 0.7411(4) 0.4183(13) 0.2470(3) 0.0186(9) Uani d . 1 . .
H H14A 0.7897 0.5209 0.3022 0.022 Uiso calc R 1 . .
C C15 0.6327(3) 0.4102(13) 0.2495(3) 0.0175(9) Uani d . 1 . .
H H15A 0.6075 0.5107 0.3065 0.021 Uiso calc R 1 . .
C C16 0.9272(3) 0.1512(18) 0.0810(3) 0.0223(11) Uani d . 1 . .
H H16A 0.9121 -0.0888 0.0783 0.033 Uiso calc R 1 . .
H H16B 1.0046 0.1870 0.0916 0.033 Uiso calc R 1 . .
H H16C 0.8930 0.2553 0.0151 0.033 Uiso calc R 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'
O O 0.0492 0.0322 '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'
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
C13 O2 C16 . . 116.7(3) ?
C2 C1 C6 . . 117.3(4) ?
C2 C1 C7 . . 125.7(4) ?
C6 C1 C7 . . 117.1(4) ?
C3 C2 C1 . . 121.9(4) ?
C3 C2 Br . . 116.4(3) ?
C1 C2 Br . . 121.7(3) ?
C2 C3 C4 . . 119.7(4) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C3 C4 C5 . . 120.1(4) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C6 C5 C4 . . 119.9(4) ?
C6 C5 H5A . . 120.1 ?
C4 C5 H5A . . 120.1 ?
C5 C6 C1 . . 121.3(4) ?
C5 C6 H6A . . 119.4 ?
C1 C6 H6A . . 119.4 ?
O1 C7 C8 . . 122.6(4) ?
O1 C7 C1 . . 118.7(4) ?
C8 C7 C1 . . 118.6(4) ?
C9 C8 C7 . . 120.5(4) ?
C9 C8 H8A . . 119.7 ?
C7 C8 H8A . . 119.7 ?
C8 C9 C10 . . 127.2(4) ?
C8 C9 H9A . . 116.4 ?
C10 C9 H9A . . 116.4 ?
C11 C10 C15 . . 117.6(4) ?
C11 C10 C9 . . 118.5(4) ?
C15 C10 C9 . . 123.9(4) ?
C12 C11 C10 . . 122.2(4) ?
C12 C11 H11A . . 118.9 ?
C10 C11 H11A . . 118.9 ?
C13 C12 C11 . . 118.9(4) ?
C13 C12 H12A . . 120.6 ?
C11 C12 H12A . . 120.6 ?
O2 C13 C12 . . 124.5(4) ?
O2 C13 C14 . . 115.1(4) ?
C12 C13 C14 . . 120.4(4) ?
C15 C14 C13 . . 119.5(4) ?
C15 C14 H14A . . 120.2 ?
C13 C14 H14A . . 120.2 ?
C14 C15 C10 . . 121.3(4) ?
C14 C15 H15A . . 119.3 ?
C10 C15 H15A . . 119.3 ?
O2 C16 H16A . . 109.5 ?
O2 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O2 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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
Br C2 . 1.907(4) ?
O1 C7 . 1.224(5) ?
O2 C13 . 1.361(5) ?
O2 C16 . 1.433(5) ?
C1 C2 . 1.396(5) ?
C1 C6 . 1.408(6) ?
C1 C7 . 1.512(5) ?
C2 C3 . 1.380(6) ?
C3 C4 . 1.384(7) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.390(6) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.379(6) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C8 . 1.471(6) ?
C8 C9 . 1.341(6) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.464(5) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.401(6) ?
C10 C15 . 1.403(6) ?
C11 C12 . 1.396(6) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.387(6) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.410(6) ?
C14 C15 . 1.387(6) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
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
C12 H12A O1 2_645 0.95 2.59 3.541(5) 174.3
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
C6 C1 C2 C3 . . . . 0.1(7) ?
C7 C1 C2 C3 . . . . -179.0(4) ?
C6 C1 C2 Br . . . . 177.7(4) ?
C7 C1 C2 Br . . . . -1.3(7) ?
C1 C2 C3 C4 . . . . -0.8(7) ?
Br C2 C3 C4 . . . . -178.6(4) ?
C2 C3 C4 C5 . . . . 0.7(8) ?
C3 C4 C5 C6 . . . . 0.2(9) ?
C4 C5 C6 C1 . . . . -1.1(8) ?
C2 C1 C6 C5 . . . . 0.9(7) ?
C7 C1 C6 C5 . . . . 180.0(4) ?
C2 C1 C7 O1 . . . . 139.4(5) ?
C6 C1 C7 O1 . . . . -39.6(7) ?
C2 C1 C7 C8 . . . . -43.2(7) ?
C6 C1 C7 C8 . . . . 137.8(5) ?
O1 C7 C8 C9 . . . . -18.2(7) ?
C1 C7 C8 C9 . . . . 164.4(4) ?
C7 C8 C9 C10 . . . . -178.4(4) ?
C8 C9 C10 C11 . . . . -170.9(4) ?
C8 C9 C10 C15 . . . . 9.4(7) ?
C15 C10 C11 C12 . . . . -2.4(6) ?
C9 C10 C11 C12 . . . . 177.9(4) ?
C10 C11 C12 C13 . . . . 1.9(6) ?
C16 O2 C13 C12 . . . . 0.2(7) ?
C16 O2 C13 C14 . . . . 179.6(5) ?
C11 C12 C13 O2 . . . . 179.4(4) ?
C11 C12 C13 C14 . . . . 0.0(6) ?
O2 C13 C14 C15 . . . . 179.2(4) ?
C12 C13 C14 C15 . . . . -1.4(7) ?
C13 C14 C15 C10 . . . . 0.8(7) ?
C11 C10 C15 C14 . . . . 1.0(7) ?
C9 C10 C15 C14 . . . . -179.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6253384
