#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227816.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227816
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Chidan Kumar, C. S.'
'Yathirajan, H. S.'
'Mayekar, A. N.'
_publ_section_title
;
 (2E)-1-(3-Bromophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one
;
_journal_coeditor_code           LX2178
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2936
_journal_page_last               o2937
_journal_paper_doi               10.1107/S1600536810041292
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H14 Br N O5'
_chemical_formula_moiety         'C17 H14 Br N O5'
_chemical_formula_sum            'C17 H14 Br N O5'
_chemical_formula_weight         392.20
_chemical_name_systematic
;
(2E)-1-(3-Bromophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8547(2)
_cell_length_b                   8.3205(2)
_cell_length_c                   27.1509(6)
_cell_measurement_reflns_used    8339
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.9455
_cell_measurement_theta_min      4.8827
_cell_volume                     1548.54(7)
_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 0.991
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Diffractometer with Ruby Gemini 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     1.54178
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9914
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.09
_diffrn_reflns_theta_min         5.56
_exptl_absorpt_coefficient_mu    3.882
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.420
_refine_ls_abs_structure_details 'Flack (1983), 1228 Friedel pairs'
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0497P)²+1.5041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                3011
_reflns_number_total             3069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2178.cif
_cod_data_source_block           I
_cod_database_code               2227816
_cod_database_fobs_code          2227816
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.59396(5) 0.54840(4) 0.757218(10) 0.02935(11) Uani d . 1 . .
O O1 0.5372(4) 0.1224(3) 0.60992(8) 0.0329(6) Uani d . 1 . .
O O2 0.7701(4) -0.1958(3) 0.50347(8) 0.0314(5) Uani d . 1 . .
O O3 0.6537(4) -0.3581(3) 0.44871(9) 0.0332(6) Uani d . 1 . .
O O4 0.5820(4) 0.0031(2) 0.30190(7) 0.0240(4) Uani d . 1 . .
O O5 0.5346(4) 0.2869(3) 0.33757(7) 0.0258(5) Uani d . 1 . .
N N1 0.6855(4) -0.2223(3) 0.46423(10) 0.0227(5) Uani d . 1 . .
C C1 0.5862(5) 0.4042(3) 0.61065(10) 0.0200(5) Uani d . 1 . .
C C2 0.5815(5) 0.4043(3) 0.66260(10) 0.0227(6) Uani d . 1 . .
H H2A 0.5685 0.3064 0.6803 0.027 Uiso calc R 1 . .
C C3 0.5960(4) 0.5491(4) 0.68724(9) 0.0229(5) Uani d . 1 . .
C C4 0.6120(5) 0.6943(4) 0.66260(11) 0.0247(6) Uani d . 1 . .
H H4A 0.6189 0.7925 0.6804 0.030 Uiso calc R 1 . .
C C5 0.6179(5) 0.6939(4) 0.61128(11) 0.0246(6) Uani d . 1 . .
H H5A 0.6296 0.7925 0.5938 0.030 Uiso calc R 1 . .
C C6 0.6065(4) 0.5491(4) 0.58544(10) 0.0230(5) Uani d . 1 . .
H H6A 0.6126 0.5494 0.5505 0.028 Uiso calc R 1 . .
C C7 0.5701(5) 0.2433(4) 0.58575(11) 0.0233(6) Uani d . 1 . .
C C8 0.5993(5) 0.2348(4) 0.53138(10) 0.0224(6) Uani d . 1 . .
H H8A 0.6323 0.3286 0.5132 0.027 Uiso calc R 1 . .
C C9 0.5783(5) 0.0934(3) 0.50851(10) 0.0213(5) Uani d . 1 . .
H H9A 0.5488 0.0027 0.5284 0.026 Uiso calc R 1 . .
C C10 0.5971(4) 0.0665(3) 0.45512(9) 0.0191(5) Uani d . 1 . .
C C11 0.6283(4) -0.0843(3) 0.43402(10) 0.0199(6) Uani d . 1 . .
C C12 0.6209(4) -0.1121(3) 0.38335(10) 0.0206(6) Uani d . 1 . .
H H12A 0.6378 -0.2178 0.3708 0.025 Uiso calc R 1 . .
C C13 0.5890(5) 0.0144(3) 0.35161(9) 0.0198(5) Uani d . 1 . .
C C14 0.5639(5) 0.1705(3) 0.37128(10) 0.0208(6) Uani d . 1 . .
C C15 0.5659(4) 0.1943(3) 0.42198(10) 0.0203(6) Uani d . 1 . .
H H15A 0.5457 0.2995 0.4346 0.024 Uiso calc R 1 . .
C C16 0.5963(5) -0.1555(4) 0.28128(10) 0.0255(6) Uani d . 1 . .
H H16A 0.5866 -0.1490 0.2453 0.038 Uiso calc R 1 . .
H H16B 0.4900 -0.2223 0.2941 0.038 Uiso calc R 1 . .
H H16C 0.7219 -0.2032 0.2904 0.038 Uiso calc R 1 . .
C C17 0.5316(6) 0.4499(4) 0.35512(11) 0.0317(7) Uani d . 1 . .
H H17A 0.5242 0.5236 0.3270 0.048 Uiso calc R 1 . .
H H17B 0.6509 0.4714 0.3739 0.048 Uiso calc R 1 . .
H H17C 0.4177 0.4657 0.3764 0.048 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
C13 O4 C16 . . 116.8(2) ?
C14 O5 C17 . . 117.1(2) ?
O3 N1 O2 . . 123.1(3) ?
O3 N1 C11 . . 118.9(3) ?
O2 N1 C11 . . 118.0(2) ?
C6 C1 C2 . . 119.5(2) ?
C6 C1 C7 . . 123.8(2) ?
C2 C1 C7 . . 116.6(2) ?
C3 C2 C1 . . 118.9(3) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 122.2(2) ?
C2 C3 Br . . 118.8(2) ?
C4 C3 Br . . 119.1(2) ?
C3 C4 C5 . . 118.9(3) ?
C3 C4 H4A . . 120.6 ?
C5 C4 H4A . . 120.6 ?
C4 C5 C6 . . 120.2(3) ?
C4 C5 H5A . . 119.9 ?
C6 C5 H5A . . 119.9 ?
C1 C6 C5 . . 120.4(2) ?
C1 C6 H6A . . 119.8 ?
C5 C6 H6A . . 119.8 ?
O1 C7 C8 . . 121.2(3) ?
O1 C7 C1 . . 120.3(3) ?
C8 C7 C1 . . 118.5(3) ?
C9 C8 C7 . . 119.1(3) ?
C9 C8 H8A . . 120.5 ?
C7 C8 H8A . . 120.5 ?
C8 C9 C10 . . 125.5(3) ?
C8 C9 H9A . . 117.2 ?
C10 C9 H9A . . 117.2 ?
C11 C10 C15 . . 116.1(2) ?
C11 C10 C9 . . 123.7(3) ?
C15 C10 C9 . . 120.0(2) ?
C10 C11 C12 . . 123.3(3) ?
C10 C11 N1 . . 121.1(2) ?
C12 C11 N1 . . 115.5(2) ?
C13 C12 C11 . . 119.7(3) ?
C13 C12 H12A . . 120.2 ?
C11 C12 H12A . . 120.2 ?
O4 C13 C12 . . 125.1(2) ?
O4 C13 C14 . . 115.9(2) ?
C12 C13 C14 . . 119.0(2) ?
O5 C14 C15 . . 124.8(3) ?
O5 C14 C13 . . 114.9(2) ?
C15 C14 C13 . . 120.2(3) ?
C14 C15 C10 . . 121.7(3) ?
C14 C15 H15A . . 119.1 ?
C10 C15 H15A . . 119.1 ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O5 C17 H17A . . 109.5 ?
O5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O5 C17 H17C . . 109.5 ?
H17A 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
Br C3 . 1.900(3) ?
O1 C7 . 1.222(4) ?
O2 N1 . 1.233(4) ?
O3 N1 . 1.225(4) ?
O4 C13 . 1.354(3) ?
O4 C16 . 1.436(3) ?
O5 C14 . 1.348(4) ?
O5 C17 . 1.437(4) ?
N1 C11 . 1.465(4) ?
C1 C6 . 1.393(4) ?
C1 C2 . 1.411(4) ?
C1 C7 . 1.504(4) ?
C2 C3 . 1.382(4) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.386(4) ?
C4 C5 . 1.394(4) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.397(4) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C8 . 1.491(4) ?
C8 C9 . 1.338(4) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.472(4) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.395(4) ?
C10 C15 . 1.410(4) ?
C11 C12 . 1.396(4) ?
C12 C13 . 1.378(4) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.415(4) ?
C14 C15 . 1.391(4) ?
C15 H15A . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 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
C16 H16A O5 3_645 0.98 2.46 3.383(3) 157.4
C17 H17B O3 1_565 0.98 2.48 3.116(4) 122.5
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 . . . . 179.9(3) ?
C1 C2 C3 C4 . . . . 1.0(5) ?
C1 C2 C3 Br . . . . -178.9(3) ?
C2 C3 C4 C5 . . . . -1.4(5) ?
Br C3 C4 C5 . . . . 178.6(3) ?
C3 C4 C5 C6 . . . . 0.4(5) ?
C2 C1 C6 C5 . . . . -1.4(5) ?
C7 C1 C6 C5 . . . . 179.1(3) ?
C4 C5 C6 C1 . . . . 1.0(5) ?
C6 C1 C7 O1 . . . . -174.2(3) ?
C2 C1 C7 O1 . . . . 6.3(5) ?
C6 C1 C7 C8 . . . . 7.0(5) ?
C2 C1 C7 C8 . . . . -172.5(3) ?
O1 C7 C8 C9 . . . . 3.7(5) ?
C1 C7 C8 C9 . . . . -177.6(3) ?
C7 C8 C9 C10 . . . . 178.3(3) ?
C8 C9 C10 C11 . . . . 161.5(3) ?
C8 C9 C10 C15 . . . . -24.4(5) ?
C15 C10 C11 C12 . . . . -2.9(4) ?
C9 C10 C11 C12 . . . . 171.4(3) ?
C15 C10 C11 N1 . . . . 172.6(3) ?
C9 C10 C11 N1 . . . . -13.0(5) ?
O3 N1 C11 C10 . . . . 157.6(3) ?
O2 N1 C11 C10 . . . . -25.0(4) ?
O3 N1 C11 C12 . . . . -26.6(4) ?
O2 N1 C11 C12 . . . . 150.9(3) ?
C10 C11 C12 C13 . . . . 2.7(5) ?
N1 C11 C12 C13 . . . . -173.1(3) ?
C16 O4 C13 C12 . . . . 4.4(5) ?
C16 O4 C13 C14 . . . . -176.6(3) ?
C11 C12 C13 O4 . . . . 178.8(3) ?
C11 C12 C13 C14 . . . . -0.2(5) ?
C17 O5 C14 C15 . . . . 8.8(5) ?
C17 O5 C14 C13 . . . . -172.7(3) ?
O4 C13 C14 O5 . . . . 0.6(4) ?
C12 C13 C14 O5 . . . . 179.7(3) ?
O4 C13 C14 C15 . . . . 179.1(3) ?
C12 C13 C14 C15 . . . . -1.8(5) ?
O5 C14 C15 C10 . . . . 179.9(3) ?
C13 C14 C15 C10 . . . . 1.5(5) ?
C11 C10 C15 C14 . . . . 0.8(4) ?
C9 C10 C15 C14 . . . . -173.8(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6252457
