#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/99/2229960.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_2229960
loop_
_publ_author_name
'Dutkiewicz, Grzegorz'
'Siddaraju, B. P.'
'Yathirajan, H. S.'
'Narayana, B.'
'Kubicki, Maciej'
_publ_section_title
;
 (2E)-3-(3-Bromo-4-methoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one
;
_journal_coeditor_code           DN2670
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1090
_journal_paper_doi               10.1107/S1600536811012505
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H12 Br F O2'
_chemical_formula_moiety         'C16 H12 Br F O2'
_chemical_formula_sum            'C16 H12 Br F O2'
_chemical_formula_weight         335.17
_chemical_name_systematic
;
(2E)-3-(3-Bromo-4-methoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one
;
_space_group_IT_number           14
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.76(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.056(2)
_cell_length_b                   4.1110(15)
_cell_length_c                   30.825(5)
_cell_measurement_reflns_used    2417
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0147
_cell_measurement_theta_min      3.0510
_cell_volume                     1391.3(6)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device_type  'Agilent Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            6983
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    2.964
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.524
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0441
_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)+(0.0450P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                1918
_reflns_number_total             2887
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2670.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229960
_cod_database_fobs_code          2229960
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 0.1287(3) 0.1073(8) 0.61784(11) 0.0453(9) Uani d . 1 . .
O O1 0.0290(2) 0.2293(7) 0.60968(8) 0.0649(7) Uani d . 1 . .
C C2 0.1926(3) 0.1062(8) 0.66297(11) 0.0427(8) Uani d . 1 . .
H H2 0.2639 -0.0139 0.6689 0.051 Uiso calc R 1 . .
C C3 0.1509(3) 0.2716(8) 0.69512(11) 0.0397(8) Uani d . 1 . .
H H3 0.0814 0.3956 0.6873 0.048 Uiso calc R 1 . .
C C4 0.1999(3) 0.2836(7) 0.74082(10) 0.0328(7) Uani d . 1 . .
C C5 0.3100(3) 0.1388(7) 0.75684(10) 0.0340(7) Uani d . 1 . .
H H5 0.3557 0.0294 0.7379 0.041 Uiso calc R 1 . .
C C6 0.3511(3) 0.1577(7) 0.80038(11) 0.0342(7) Uani d . 1 . .
Br Br6 0.50370(3) -0.02669(8) 0.820926(12) 0.05081(15) Uani d . 1 . .
C C7 0.2842(3) 0.3147(7) 0.83016(10) 0.0370(8) Uani d . 1 . .
O O7 0.3326(2) 0.3123(6) 0.87212(7) 0.0539(7) Uani d . 1 . .
C C71 0.2665(4) 0.4821(10) 0.90272(13) 0.0834(15) Uani d . 1 . .
H H71A 0.1882 0.3821 0.9033 0.125 Uiso calc R 1 . .
H H71B 0.2558 0.7053 0.8939 0.125 Uiso calc R 1 . .
H H71C 0.3114 0.4722 0.9313 0.125 Uiso calc R 1 . .
C C8 0.1740(3) 0.4534(7) 0.81422(12) 0.0434(8) Uani d . 1 . .
H H8 0.1263 0.5534 0.8333 0.052 Uiso calc R 1 . .
C C9 0.1346(3) 0.4439(7) 0.77032(12) 0.0414(8) Uani d . 1 . .
H H9 0.0622 0.5477 0.7600 0.050 Uiso calc R 1 . .
C C11 0.1903(3) -0.0519(8) 0.58326(10) 0.0414(8) Uani d . 1 . .
C C12 0.3150(3) -0.1039(9) 0.58687(12) 0.0549(10) Uani d . 1 . .
H H12 0.3634 -0.0397 0.6121 0.066 Uiso calc R 1 . .
C C13 0.3682(4) -0.2492(10) 0.55362(13) 0.0653(11) Uani d . 1 . .
H H13 0.4519 -0.2840 0.5562 0.078 Uiso calc R 1 . .
C C14 0.2958(4) -0.3405(10) 0.51699(13) 0.0647(11) Uani d . 1 . .
F F14 0.3475(3) -0.4875(6) 0.48435(9) 0.1010(9) Uani d . 1 . .
C C15 0.1731(4) -0.2938(10) 0.51172(13) 0.0664(11) Uani d . 1 . .
H H15 0.1257 -0.3590 0.4863 0.080 Uiso calc R 1 . .
C C16 0.1211(3) -0.1476(10) 0.54502(12) 0.0579(10) Uani d . 1 . .
H H16 0.0375 -0.1121 0.5418 0.069 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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C11 . . 121.2(3) ?
O1 C1 C2 . . 121.1(3) ?
C11 C1 C2 . . 117.7(3) ?
C3 C2 C1 . . 122.0(3) ?
C3 C2 H2 . . 119.0 ?
C1 C2 H2 . . 119.0 ?
C2 C3 C4 . . 128.3(3) ?
C2 C3 H3 . . 115.8 ?
C4 C3 H3 . . 115.8 ?
C9 C4 C5 . . 118.0(3) ?
C9 C4 C3 . . 119.2(3) ?
C5 C4 C3 . . 122.8(3) ?
C6 C5 C4 . . 119.9(3) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C7 . . 122.0(3) ?
C5 C6 Br6 . . 119.1(2) ?
C7 C6 Br6 . . 118.9(2) ?
O7 C7 C8 . . 125.5(3) ?
O7 C7 C6 . . 116.6(3) ?
C8 C7 C6 . . 117.9(3) ?
C7 O7 C71 . . 117.0(3) ?
O7 C71 H71A . . 109.5 ?
O7 C71 H71B . . 109.5 ?
H71A C71 H71B . . 109.5 ?
O7 C71 H71C . . 109.5 ?
H71A C71 H71C . . 109.5 ?
H71B C71 H71C . . 109.5 ?
C9 C8 C7 . . 120.1(3) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C4 . . 122.0(3) ?
C8 C9 H9 . . 119.0 ?
C4 C9 H9 . . 119.0 ?
C16 C11 C12 . . 118.0(3) ?
C16 C11 C1 . . 118.9(3) ?
C12 C11 C1 . . 123.1(3) ?
C13 C12 C11 . . 121.0(3) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C14 C13 C12 . . 118.5(4) ?
C14 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
F14 C14 C13 . . 118.8(4) ?
F14 C14 C15 . . 118.4(4) ?
C13 C14 C15 . . 122.8(4) ?
C14 C15 C16 . . 118.1(4) ?
C14 C15 H15 . . 120.9 ?
C16 C15 H15 . . 120.9 ?
C15 C16 C11 . . 121.6(4) ?
C15 C16 H16 . . 119.2 ?
C11 C16 H16 . . 119.2 ?
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 . 1.210(4) ?
C1 C11 . 1.483(5) ?
C1 C2 . 1.484(5) ?
C2 C3 . 1.328(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.449(4) ?
C3 H3 . 0.9300 ?
C4 C9 . 1.391(4) ?
C4 C5 . 1.393(4) ?
C5 C6 . 1.367(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.402(4) ?
C6 Br6 . 1.890(3) ?
C7 O7 . 1.340(4) ?
C7 C8 . 1.383(4) ?
O7 C71 . 1.440(4) ?
C71 H71A . 0.9600 ?
C71 H71B . 0.9600 ?
C71 H71C . 0.9600 ?
C8 C9 . 1.372(5) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C11 C16 . 1.385(5) ?
C11 C12 . 1.387(4) ?
C12 C13 . 1.377(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.358(5) ?
C13 H13 . 0.9300 ?
C14 F14 . 1.357(4) ?
C14 C15 . 1.361(5) ?
C15 C16 . 1.372(5) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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 . . . . -8.4(5) ?
C11 C1 C2 C3 . . . . 172.8(3) ?
C1 C2 C3 C4 . . . . 177.2(3) ?
C2 C3 C4 C9 . . . . -172.8(3) ?
C2 C3 C4 C5 . . . . 6.7(5) ?
C9 C4 C5 C6 . . . . -0.2(4) ?
C3 C4 C5 C6 . . . . -179.7(3) ?
C4 C5 C6 C7 . . . . 1.2(4) ?
C4 C5 C6 Br6 . . . . -177.6(2) ?
C5 C6 C7 O7 . . . . 178.8(3) ?
Br6 C6 C7 O7 . . . . -2.3(4) ?
C5 C6 C7 C8 . . . . -0.2(5) ?
Br6 C6 C7 C8 . . . . 178.7(2) ?
C8 C7 O7 C71 . . . . -3.1(5) ?
C6 C7 O7 C71 . . . . 178.0(3) ?
O7 C7 C8 C9 . . . . 179.2(3) ?
C6 C7 C8 C9 . . . . -2.0(5) ?
C7 C8 C9 C4 . . . . 3.2(5) ?
C5 C4 C9 C8 . . . . -2.0(4) ?
C3 C4 C9 C8 . . . . 177.6(3) ?
O1 C1 C11 C16 . . . . -19.2(5) ?
C2 C1 C11 C16 . . . . 159.6(3) ?
O1 C1 C11 C12 . . . . 159.3(3) ?
C2 C1 C11 C12 . . . . -21.8(5) ?
C16 C11 C12 C13 . . . . -0.6(5) ?
C1 C11 C12 C13 . . . . -179.2(3) ?
C11 C12 C13 C14 . . . . 0.1(6) ?
C12 C13 C14 F14 . . . . -179.2(3) ?
C12 C13 C14 C15 . . . . 0.2(6) ?
F14 C14 C15 C16 . . . . 179.4(4) ?
C13 C14 C15 C16 . . . . 0.1(6) ?
C14 C15 C16 C11 . . . . -0.6(6) ?
C12 C11 C16 C15 . . . . 0.9(6) ?
C1 C11 C16 C15 . . . . 179.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6496377
