#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229165.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_2229165
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Samshuddin, S.'
'Narayana, B.'
'Yathirajan, H. S.'
_publ_section_title
;
 (2E)-3-(3-Bromo-4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one
;
_journal_coeditor_code           NG5098
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o352
_journal_page_last               o353
_journal_paper_doi               10.1107/S1600536811000353
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H12 Br N O2'
_chemical_formula_moiety         'C15 H12 Br N O2'
_chemical_formula_sum            'C15 H12 Br N O2'
_chemical_formula_weight         318.17
_chemical_name_systematic
;
(2E)-3-(3-Bromo-4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 113.892(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.3402(13)
_cell_length_b                   3.8906(2)
_cell_length_c                   27.5826(17)
_cell_measurement_reflns_used    3510
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.9947
_cell_measurement_theta_min      4.6625
_cell_volume                     2584.4(3)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (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      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            3978
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.09
_diffrn_reflns_theta_min         6.02
_exptl_absorpt_coefficient_mu    4.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.640
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0704P)²+6.6225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                2431
_reflns_number_total             2556
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5098.cif
_cod_data_source_block           I
_cod_original_cell_volume        2584.4(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229165
_cod_database_fobs_code          2229165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Br Br1 0.046034(12) 0.06121(9) 0.063358(11) 0.03852(15) Uani d . 1 . .
O O1 0.36895(11) 0.4707(8) 0.17800(10) 0.0507(6) Uani d . 1 . .
O O2 0.04309(8) 0.3262(7) 0.16281(8) 0.0431(5) Uani d . 1 . .
N N1 0.30803(11) 0.0395(8) 0.05431(11) 0.0410(6) Uani d . 1 . .
C C1 0.34866(11) 0.1894(9) 0.09571(12) 0.0359(6) Uani d . 1 . .
C C2 0.40303(12) 0.2175(8) 0.10013(13) 0.0382(6) Uani d . 1 . .
H H2A 0.4308 0.3251 0.1300 0.046 Uiso calc R 1 . .
C C3 0.41559(13) 0.0837(9) 0.05953(15) 0.0441(8) Uani d . 1 . .
H H3A 0.4523 0.0956 0.0614 0.053 Uiso calc R 1 . .
C C4 0.37382(15) -0.0664(9) 0.01663(15) 0.0451(8) Uani d . 1 . .
H H4A 0.3812 -0.1569 -0.0119 0.054 Uiso calc R 1 . .
C C5 0.32078(15) -0.0833(9) 0.01567(14) 0.0442(8) Uani d . 1 . .
H H5A 0.2922 -0.1875 -0.0140 0.053 Uiso calc R 1 . .
C C6 0.33420(13) 0.3330(10) 0.13914(12) 0.0420(7) Uani d . 1 . .
C C7 0.27542(13) 0.3026(9) 0.13151(12) 0.0410(7) Uani d . 1 . .
H H7A 0.2503 0.1747 0.1023 0.049 Uiso calc R 1 . .
C C8 0.25712(14) 0.4531(9) 0.16526(13) 0.0404(7) Uani d . 1 . .
H H8A 0.2833 0.5857 0.1931 0.048 Uiso calc R 1 . .
C C9 0.20072(13) 0.4324(9) 0.16324(12) 0.0389(7) Uani d . 1 . .
C C10 0.15685(12) 0.2790(9) 0.12093(11) 0.0359(6) Uani d . 1 . .
H H10A 0.1628 0.1909 0.0915 0.043 Uiso calc R 1 . .
C C11 0.10531(11) 0.2558(7) 0.12193(11) 0.0311(6) Uani d . 1 . .
C C12 0.09521(12) 0.3743(8) 0.16536(11) 0.0335(6) Uani d . 1 . .
C C13 0.13844(13) 0.5282(9) 0.20707(13) 0.0374(7) Uani d . 1 . .
H H13A 0.1327 0.6135 0.2367 0.045 Uiso calc R 1 . .
C C14 0.19004(14) 0.5571(9) 0.20544(13) 0.0395(7) Uani d . 1 . .
H H14A 0.2192 0.6660 0.2341 0.047 Uiso calc R 1 . .
C C15 0.03317(15) 0.4373(11) 0.20775(14) 0.0489(9) Uani d . 1 . .
H H15A -0.0049 0.3784 0.2024 0.073 Uiso calc R 1 . .
H H15B 0.0383 0.6868 0.2118 0.073 Uiso calc R 1 . .
H H15C 0.0594 0.3227 0.2398 0.073 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'
N N 0.0311 0.0180 '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
C12 O2 C15 . . 116.6(3) ?
C5 N1 C1 . . 117.7(3) ?
N1 C1 C2 . . 123.1(3) ?
N1 C1 C6 . . 117.9(3) ?
C2 C1 C6 . . 119.0(3) ?
C3 C2 C1 . . 118.2(3) ?
C3 C2 H2A . . 120.9 ?
C1 C2 H2A . . 120.9 ?
C4 C3 C2 . . 118.9(3) ?
C4 C3 H3A . . 120.6 ?
C2 C3 H3A . . 120.6 ?
C3 C4 C5 . . 118.9(3) ?
C3 C4 H4A . . 120.5 ?
C5 C4 H4A . . 120.5 ?
N1 C5 C4 . . 123.2(3) ?
N1 C5 H5A . . 118.4 ?
C4 C5 H5A . . 118.4 ?
O1 C6 C7 . . 122.1(3) ?
O1 C6 C1 . . 121.5(3) ?
C7 C6 C1 . . 116.4(3) ?
C8 C7 C6 . . 121.0(3) ?
C8 C7 H7A . . 119.5 ?
C6 C7 H7A . . 119.5 ?
C7 C8 C9 . . 126.3(3) ?
C7 C8 H8A . . 116.8 ?
C9 C8 H8A . . 116.8 ?
C14 C9 C10 . . 117.9(3) ?
C14 C9 C8 . . 119.6(3) ?
C10 C9 C8 . . 122.4(3) ?
C11 C10 C9 . . 120.0(3) ?
C11 C10 H10A . . 120.0 ?
C9 C10 H10A . . 120.0 ?
C10 C11 C12 . . 121.7(3) ?
C10 C11 Br1 . . 119.4(2) ?
C12 C11 Br1 . . 118.9(2) ?
O2 C12 C13 . . 125.2(3) ?
O2 C12 C11 . . 116.5(3) ?
C13 C12 C11 . . 118.3(3) ?
C14 C13 C12 . . 119.8(3) ?
C14 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
C13 C14 C9 . . 122.2(3) ?
C13 C14 H14A . . 118.9 ?
C9 C14 H14A . . 118.9 ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 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 C11 . 1.892(3) ?
O1 C6 . 1.216(4) ?
O2 C12 . 1.359(3) ?
O2 C15 . 1.433(4) ?
N1 C5 . 1.329(5) ?
N1 C1 . 1.341(4) ?
C1 C2 . 1.391(4) ?
C1 C6 . 1.504(5) ?
C2 C3 . 1.391(5) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.377(5) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.388(5) ?
C4 H4A . 0.9500 ?
C5 H5A . 0.9500 ?
C6 C7 . 1.480(4) ?
C7 C8 . 1.344(5) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.466(4) ?
C8 H8A . 0.9500 ?
C9 C14 . 1.391(5) ?
C9 C10 . 1.400(5) ?
C10 C11 . 1.372(4) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.406(4) ?
C12 C13 . 1.385(4) ?
C13 C14 . 1.383(5) ?
C13 H13A . 0.9500 ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 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
C3 H3A Br1 3 0.95 3.04 3.870(3) 146
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
C5 N1 C1 C2 . . . . -0.8(5) ?
C5 N1 C1 C6 . . . . 179.2(3) ?
N1 C1 C2 C3 . . . . 0.1(5) ?
C6 C1 C2 C3 . . . . -179.9(3) ?
C1 C2 C3 C4 . . . . 0.8(5) ?
C2 C3 C4 C5 . . . . -0.9(5) ?
C1 N1 C5 C4 . . . . 0.7(5) ?
C3 C4 C5 N1 . . . . 0.1(5) ?
N1 C1 C6 O1 . . . . 179.6(3) ?
C2 C1 C6 O1 . . . . -0.4(5) ?
N1 C1 C6 C7 . . . . -1.4(4) ?
C2 C1 C6 C7 . . . . 178.6(3) ?
O1 C6 C7 C8 . . . . 5.8(6) ?
C1 C6 C7 C8 . . . . -173.2(3) ?
C6 C7 C8 C9 . . . . -177.7(3) ?
C7 C8 C9 C14 . . . . 170.1(3) ?
C7 C8 C9 C10 . . . . -7.5(5) ?
C14 C9 C10 C11 . . . . 0.1(5) ?
C8 C9 C10 C11 . . . . 177.7(3) ?
C9 C10 C11 C12 . . . . -1.8(5) ?
C9 C10 C11 Br1 . . . . 178.0(2) ?
C15 O2 C12 C13 . . . . -1.6(5) ?
C15 O2 C12 C11 . . . . 178.1(3) ?
C10 C11 C12 O2 . . . . -177.6(3) ?
Br1 C11 C12 O2 . . . . 2.7(4) ?
C10 C11 C12 C13 . . . . 2.2(5) ?
Br1 C11 C12 C13 . . . . -177.6(2) ?
O2 C12 C13 C14 . . . . 178.9(3) ?
C11 C12 C13 C14 . . . . -0.9(5) ?
C12 C13 C14 C9 . . . . -0.8(5) ?
C10 C9 C14 C13 . . . . 1.2(5) ?
C8 C9 C14 C13 . . . . -176.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25911848
