#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226855.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_2226855
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Veena, K.'
'Narayana, B.'
'Yathirajan, H. S.'
_publ_section_title
;
 (E)-1-(2-Bromophenyl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           FB2201
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1952
_journal_paper_doi               10.1107/S1600536810025638
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H15 Br O3'
_chemical_formula_moiety         'C17 H15 Br O3'
_chemical_formula_sum            'C17 H15 Br O3'
_chemical_formula_weight         347.20
_chemical_melting_point_gt       355
_chemical_melting_point_lt       357
_chemical_name_systematic
;
(E)-1-(2-Bromophenyl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                72.901(10)
_cell_angle_beta                 78.487(9)
_cell_angle_gamma                86.359(9)
_cell_formula_units_Z            2
_cell_length_a                   7.7643(9)
_cell_length_b                   9.7006(11)
_cell_length_c                   10.2722(10)
_cell_measurement_reflns_used    4418
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      73.9045
_cell_measurement_theta_min      4.5929
_cell_volume                     724.60(14)
_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 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
;
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4759
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.18
_diffrn_reflns_theta_min         4.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.933
_exptl_absorpt_correction_T_max  0.635
_exptl_absorpt_correction_T_min  0.179
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlisRED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'triangular plate'
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.077
_refine_diff_density_max         2.505
_refine_diff_density_min         -1.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0532
_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)+(0.1005P)²+1.9956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                2749
_reflns_number_total             2835
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2201.cif
_cod_data_source_block           I
_cod_original_cell_volume        724.59(14)
_cod_database_code               2226855
_cod_database_fobs_code          2226855
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.28123(4) 1.19671(4) -0.00743(4) 0.01849(18) Uani d . 1 . .
O O1 0.1583(4) 1.1329(3) 0.3257(3) 0.0208(6) Uani d . 1 . .
O O2 0.4450(3) 0.5470(3) 0.2755(3) 0.0161(5) Uani d . 1 . .
O O3 0.0011(4) 0.4011(3) 0.7884(3) 0.0177(5) Uani d . 1 . .
C C1 0.4421(5) 1.0666(3) 0.2299(4) 0.0129(7) Uani d . 1 . .
C C2 0.4701(5) 1.1455(4) 0.0894(4) 0.0135(7) Uani d . 1 . .
C C3 0.6379(5) 1.1881(4) 0.0155(4) 0.0160(7) Uani d . 1 . .
H H3 0.6548 1.2397 -0.0802 0.019 Uiso calc R 1 . .
C C4 0.7801(5) 1.1552(4) 0.0819(4) 0.0194(8) Uani d . 1 . .
H H4 0.8945 1.1857 0.0318 0.023 Uiso calc R 1 . .
C C5 0.7563(5) 1.0772(4) 0.2223(4) 0.0203(8) Uani d . 1 . .
H H5 0.8536 1.0560 0.2684 0.024 Uiso calc R 1 . .
C C6 0.5884(5) 1.0312(4) 0.2936(4) 0.0164(7) Uani d . 1 . .
H H6 0.5729 0.9743 0.3878 0.020 Uiso calc R 1 . .
C C7 0.2612(5) 1.0331(4) 0.3178(4) 0.0138(7) Uani d . 1 . .
C C8 0.2125(5) 0.8849(4) 0.3976(4) 0.0138(7) Uani d . 1 . .
H H8 0.1094 0.8697 0.4676 0.017 Uiso calc R 1 . .
C C9 0.3058(4) 0.7685(4) 0.3774(3) 0.0119(6) Uani d . 1 . .
H H9 0.4086 0.7848 0.3070 0.014 Uiso calc R 1 . .
C C10 0.2606(4) 0.6188(3) 0.4558(3) 0.0103(6) Uani d . 1 . .
C C11 0.3385(4) 0.5059(4) 0.4034(3) 0.0116(6) Uani d . 1 . .
C C12 0.3018(5) 0.3629(4) 0.4806(4) 0.0141(7) Uani d . 1 . .
H H12 0.3535 0.2865 0.4454 0.017 Uiso calc R 1 . .
C C13 0.1900(5) 0.3323(4) 0.6086(4) 0.0149(7) Uani d . 1 . .
H H13 0.1676 0.2348 0.6617 0.018 Uiso calc R 1 . .
C C14 0.1098(5) 0.4435(4) 0.6606(4) 0.0128(7) Uani d . 1 . .
C C15 0.1450(4) 0.5854(4) 0.5843(3) 0.0116(6) Uani d . 1 . .
H H15 0.0903 0.6611 0.6193 0.014 Uiso calc R 1 . .
C C16 0.5285(5) 0.4359(4) 0.2187(4) 0.0184(7) Uani d . 1 . .
H H16 0.6043 0.4798 0.1291 0.028 Uiso calc R 1 . .
H H16B 0.4388 0.3772 0.2057 0.028 Uiso calc R 1 . .
H H16C 0.5996 0.3747 0.2825 0.028 Uiso calc R 1 . .
C C17 -0.0777(5) 0.5153(4) 0.8422(4) 0.0174(7) Uani d . 1 . .
H H17 -0.1553 0.4744 0.9317 0.026 Uiso calc R 1 . .
H H17B -0.1463 0.5775 0.7770 0.026 Uiso calc R 1 . .
H H17C 0.0144 0.5721 0.8548 0.026 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
C11 O2 C16 . . 117.8(3) ?
C14 O3 C17 . . 115.6(3) ?
C6 C1 C2 . . 117.9(3) ?
C6 C1 C7 . . 118.9(3) ?
C2 C1 C7 . . 122.8(3) ?
C3 C2 C1 . . 121.2(3) ?
C3 C2 Br1 . . 117.5(3) ?
C1 C2 Br1 . . 121.3(3) ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.4(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 119.1(4) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C1 . . 121.5(3) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
O1 C7 C8 . . 120.6(3) ?
O1 C7 C1 . . 118.9(3) ?
C8 C7 C1 . . 120.5(3) ?
C9 C8 C7 . . 123.6(3) ?
C9 C8 H8 . . 118.2 ?
C7 C8 H8 . . 118.2 ?
C8 C9 C10 . . 124.9(3) ?
C8 C9 H9 . . 117.6 ?
C10 C9 H9 . . 117.6 ?
C15 C10 C11 . . 119.3(3) ?
C15 C10 C9 . . 121.1(3) ?
C11 C10 C9 . . 119.5(3) ?
O2 C11 C12 . . 124.4(3) ?
O2 C11 C10 . . 115.8(3) ?
C12 C11 C10 . . 119.8(3) ?
C13 C12 C11 . . 120.0(3) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.7(3) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
O3 C14 C15 . . 124.5(3) ?
O3 C14 C13 . . 115.9(3) ?
C15 C14 C13 . . 119.6(3) ?
C14 C15 C10 . . 120.6(3) ?
C14 C15 H15 . . 119.7 ?
C10 C15 H15 . . 119.7 ?
O2 C16 H16 . . 109.5 ?
O2 C16 H16B . . 109.5 ?
H16 C16 H16B . . 109.5 ?
O2 C16 H16C . . 109.5 ?
H16 C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O3 C17 H17 . . 109.5 ?
O3 C17 H17B . . 109.5 ?
H17 C17 H17B . . 109.5 ?
O3 C17 H17C . . 109.5 ?
H17 C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
Br1 C2 . 1.893(4) ?
O1 C7 . 1.227(4) ?
O2 C11 . 1.367(4) ?
O2 C16 . 1.433(4) ?
O3 C14 . 1.375(4) ?
O3 C17 . 1.430(4) ?
C1 C6 . 1.397(5) ?
C1 C2 . 1.401(5) ?
C1 C7 . 1.507(5) ?
C2 C3 . 1.391(5) ?
C3 C4 . 1.383(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.399(6) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.392(5) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.461(4) ?
C8 C9 . 1.348(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.465(4) ?
C9 H9 . 0.9500 ?
C10 C15 . 1.402(5) ?
C10 C11 . 1.410(5) ?
C11 C12 . 1.396(5) ?
C12 C13 . 1.384(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.399(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.383(5) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17 . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 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
C4 H4 Br1 1_655 0.95 2.95 3.834(4) 154.7
C3 H3 O2 2_675 0.95 2.62 3.463(5) 147.6
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 . . . . -0.4(5) ?
C7 C1 C2 C3 . . . . 172.8(3) ?
C6 C1 C2 Br1 . . . . 179.1(2) ?
C7 C1 C2 Br1 . . . . -7.7(5) ?
C1 C2 C3 C4 . . . . -1.4(5) ?
Br1 C2 C3 C4 . . . . 179.1(3) ?
C2 C3 C4 C5 . . . . 1.1(5) ?
C3 C4 C5 C6 . . . . 1.1(6) ?
C4 C5 C6 C1 . . . . -3.0(5) ?
C2 C1 C6 C5 . . . . 2.6(5) ?
C7 C1 C6 C5 . . . . -170.8(3) ?
C6 C1 C7 O1 . . . . 117.6(4) ?
C2 C1 C7 O1 . . . . -55.5(5) ?
C6 C1 C7 C8 . . . . -59.4(4) ?
C2 C1 C7 C8 . . . . 127.4(4) ?
O1 C7 C8 C9 . . . . 168.8(4) ?
C1 C7 C8 C9 . . . . -14.3(5) ?
C7 C8 C9 C10 . . . . 179.9(3) ?
C8 C9 C10 C15 . . . . -18.5(5) ?
C8 C9 C10 C11 . . . . 163.4(3) ?
C16 O2 C11 C12 . . . . -1.9(5) ?
C16 O2 C11 C10 . . . . 179.4(3) ?
C15 C10 C11 O2 . . . . 177.9(3) ?
C9 C10 C11 O2 . . . . -4.0(5) ?
C15 C10 C11 C12 . . . . -0.9(5) ?
C9 C10 C11 C12 . . . . 177.2(3) ?
O2 C11 C12 C13 . . . . -179.1(3) ?
C10 C11 C12 C13 . . . . -0.4(5) ?
C11 C12 C13 C14 . . . . 1.4(5) ?
C17 O3 C14 C15 . . . . -0.1(5) ?
C17 O3 C14 C13 . . . . 178.8(3) ?
C12 C13 C14 O3 . . . . 179.9(3) ?
C12 C13 C14 C15 . . . . -1.1(5) ?
O3 C14 C15 C10 . . . . 178.7(3) ?
C13 C14 C15 C10 . . . . -0.2(5) ?
C11 C10 C15 C14 . . . . 1.2(5) ?
C9 C10 C15 C14 . . . . -176.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9813549
