#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/09/2220949.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_2220949
loop_
_publ_author_name
'Khalaji, Aliakbar Dehno'
'Weil, Matthias'
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 4-Bromo-N-(3,4,5-trimethoxybenzylidene)aniline
;
_journal_coeditor_code           WN2308
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o436
_journal_paper_doi               10.1107/S1600536809003432
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H16 Br N O3'
_chemical_formula_moiety         'C16 H16 Br N O3'
_chemical_formula_sum            'C16 H16 Br N O3'
_chemical_formula_weight         350.21
_chemical_name_systematic
;
4-Bromo-N-(3,4,5-trimethoxybenzylidene)aniline
;
_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                 104.413(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1951(4)
_cell_length_b                   8.3722(5)
_cell_length_c                   13.2882(8)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.975
_cell_measurement_theta_min      2.923
_cell_volume                     775.27(8)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18229
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.660
_exptl_absorpt_correction_T_max  0.671
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.530
_refine_ls_abs_structure_details 'Flack (1983), 1511 Friedel pairs'
_refine_ls_abs_structure_Flack   0.012(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0339P)²+0.0173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0650
_reflns_number_gt                3064
_reflns_number_total             3497
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2308.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2220949
_cod_database_fobs_code          2220949
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 Br1 0.99402(3) 0.96811(5) 0.988948(16) 0.06694(9) Uani d . 1 . .
O O1 -0.26888(18) 0.4772(2) 0.36904(9) 0.0522(3) Uani d . 1 . .
O O2 -0.46171(19) 0.29368(19) 0.46988(11) 0.0498(3) Uani d . 1 . .
O O3 -0.3668(2) 0.2687(2) 0.67538(12) 0.0600(4) Uani d . 1 . .
N N1 0.2656(2) 0.6014(2) 0.79047(14) 0.0502(4) Uani d . 1 . .
C C1 0.7715(3) 0.8470(2) 0.92769(15) 0.0450(4) Uani d . 1 . .
C C2 0.6245(3) 0.8386(3) 0.97682(18) 0.0595(6) Uani d . 1 . .
H H2 0.6355 0.8891 1.0404 0.071 Uiso calc R 1 . .
C C3 0.4614(4) 0.7546(3) 0.9308(2) 0.0604(6) Uani d . 1 . .
H H3 0.3634 0.7458 0.9648 0.072 Uiso calc R 1 . .
C C4 0.4402(3) 0.6827(2) 0.83465(15) 0.0436(4) Uani d . 1 . .
C C5 0.5939(3) 0.6886(3) 0.78856(16) 0.0478(5) Uani d . 1 . .
H H5 0.5850 0.6368 0.7256 0.057 Uiso calc R 1 . .
C C6 0.7594(3) 0.7705(3) 0.83532(17) 0.0498(5) Uani d . 1 . .
H H6 0.8618 0.7736 0.8043 0.060 Uiso calc R 1 . .
C C7 0.2013(3) 0.6071(2) 0.69260(16) 0.0427(4) Uani d . 1 . .
H H7 0.2700 0.6651 0.6542 0.051 Uiso calc R 1 . .
C C8 0.0246(3) 0.5272(2) 0.63686(16) 0.0411(4) Uani d . 1 . .
C C9 -0.0833(3) 0.4364(2) 0.69019(15) 0.0432(5) Uani d . 1 . .
H H9 -0.0454 0.4266 0.7621 0.052 Uiso calc R 1 . .
C C10 -0.2484(3) 0.3611(2) 0.63335(16) 0.0430(4) Uani d . 1 . .
C C11 -0.3059(3) 0.3758(2) 0.52599(16) 0.0411(4) Uani d . 1 . .
C C12 -0.1991(2) 0.4695(3) 0.47377(12) 0.0403(3) Uani d . 1 . .
C C13 -0.0336(3) 0.5450(2) 0.53043(16) 0.0417(4) Uani d . 1 . .
H H13 0.0381 0.6078 0.4963 0.050 Uiso calc R 1 . .
C C14 -0.1666(4) 0.5679(4) 0.3108(2) 0.0785(8) Uani d . 1 . .
H H14A -0.1641 0.6779 0.3316 0.118 Uiso calc R 1 . .
H H14B -0.2287 0.5591 0.2382 0.118 Uiso calc R 1 . .
H H14C -0.0377 0.5284 0.3232 0.118 Uiso calc R 1 . .
C C15 -0.6378(3) 0.3769(4) 0.4588(2) 0.0673(7) Uani d . 1 . .
H H15A -0.6588 0.3972 0.5262 0.101 Uiso calc R 1 . .
H H15B -0.7412 0.3133 0.4189 0.101 Uiso calc R 1 . .
H H15C -0.6324 0.4765 0.4238 0.101 Uiso calc R 1 . .
C C16 -0.3111(5) 0.2366(4) 0.7828(2) 0.0761(8) Uani d . 1 . .
H H16A -0.1813 0.1983 0.8010 0.114 Uiso calc R 1 . .
H H16B -0.3944 0.1569 0.7997 0.114 Uiso calc R 1 . .
H H16C -0.3198 0.3327 0.8208 0.114 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'
N N 0.0061 0.0033 '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'
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 C12 C11 . . 115.25(16) ?
O1 C12 C13 . . 125.52(17) ?
O1 C14 H14A . . 109.5 ?
O1 C14 H14B . . 109.5 ?
O1 C14 H14C . . 109.5 ?
O2 C11 C10 . . 120.65(17) ?
O2 C11 C12 . . 119.28(17) ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
O3 C10 C9 . . 124.70(18) ?
O3 C10 C11 . . 114.39(17) ?
O3 C16 H16A . . 109.5 ?
O3 C16 H16B . . 109.5 ?
O3 C16 H16C . . 109.5 ?
N1 C7 C8 . . 123.41(18) ?
N1 C7 H7 . . 118.3 ?
C1 C2 H2 . . 120.4 ?
C1 C6 C5 . . 119.45(19) ?
C1 C6 H6 . . 120.3 ?
C2 C1 Br1 . . 119.30(15) ?
C2 C3 C4 . . 121.2(2) ?
C2 C3 H3 . . 119.4 ?
C3 C2 C1 . . 119.1(2) ?
C3 C2 H2 . . 120.4 ?
C3 C4 N1 . . 118.17(18) ?
C3 C4 C5 . . 118.22(19) ?
C4 C3 H3 . . 119.4 ?
C4 C5 H5 . . 119.7 ?
C5 C4 N1 . . 123.56(17) ?
C5 C6 H6 . . 120.3 ?
C6 C1 Br1 . . 119.56(16) ?
C6 C1 C2 . . 121.14(18) ?
C6 C5 C4 . . 120.69(19) ?
C6 C5 H5 . . 119.7 ?
C7 N1 C4 . . 117.70(17) ?
C8 C7 H7 . . 118.3 ?
C8 C9 H9 . . 120.7 ?
C8 C13 C12 . . 120.43(18) ?
C8 C13 H13 . . 119.8 ?
C9 C8 C7 . . 120.90(18) ?
C10 O3 C16 . . 118.18(19) ?
C10 C9 C8 . . 118.58(18) ?
C10 C9 H9 . . 120.7 ?
C10 C11 C12 . . 120.00(17) ?
C11 O2 C15 . . 113.49(18) ?
C11 C10 C9 . . 120.91(17) ?
C12 O1 C14 . . 118.41(17) ?
C13 C8 C9 . . 120.83(17) ?
C13 C8 C7 . . 118.27(17) ?
C13 C12 C11 . . 119.23(16) ?
C12 C13 H13 . . 119.8 ?
H14A C14 H14B . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
H16A C16 H16B . . 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
Br1 C1 . 1.8992(19) ?
O1 C12 . 1.358(2) ?
O1 C14 . 1.414(3) ?
O2 C11 . 1.367(2) ?
O2 C15 . 1.421(3) ?
O3 C16 . 1.409(3) ?
O3 C10 . 1.368(2) ?
C1 C2 . 1.376(3) ?
C1 C6 . 1.368(3) ?
C2 H2 . 0.9300 ?
C3 C2 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 N1 . 1.421(2) ?
C4 C3 . 1.386(3) ?
C4 C5 . 1.392(3) ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.268(3) ?
C7 C8 . 1.464(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.399(3) ?
C8 C13 . 1.379(3) ?
C9 H9 . 0.9300 ?
C10 C9 . 1.390(3) ?
C11 C10 . 1.388(3) ?
C12 C13 . 1.392(3) ?
C12 C11 . 1.397(3) ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
_geom_hbond_publ_flag
C7 H7 O1 2_556 0.93 2.63 3.272(2) 127 y
C7 H7 O2 2_556 0.93 2.63 3.553(3) 172 y
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
Br1 C1 C2 C3 . . . . 178.2(2) ?
Br1 C1 C6 C5 . . . . -177.04(17) ?
O1 C12 C11 O2 . . . . 3.6(3) ?
O1 C12 C11 C10 . . . . -179.35(19) ?
O1 C12 C13 C8 . . . . -179.36(19) ?
O2 C11 C10 O3 . . . . -4.2(3) ?
O2 C11 C10 C9 . . . . 175.96(17) ?
O3 C10 C9 C8 . . . . 179.93(18) ?
N1 C4 C3 C2 . . . . -178.3(2) ?
N1 C4 C5 C6 . . . . 179.6(2) ?
N1 C7 C8 C13 . . . . 178.51(19) ?
N1 C7 C8 C9 . . . . -0.9(3) ?
C2 C1 C6 C5 . . . . 2.6(3) ?
C3 C4 N1 C7 . . . . 144.8(2) ?
C3 C4 C5 C6 . . . . -3.0(3) ?
C4 C3 C2 C1 . . . . -2.0(4) ?
C4 C5 C6 C1 . . . . -0.3(4) ?
C5 C4 C3 C2 . . . . 4.2(4) ?
C5 C4 N1 C7 . . . . -37.8(3) ?
C6 C1 C2 C3 . . . . -1.4(4) ?
C7 C8 C9 C10 . . . . -179.05(17) ?
C7 C8 C13 C12 . . . . 179.05(18) ?
C8 C7 N1 C4 . . . . 179.19(18) ?
C9 C10 O3 C16 . . . . -5.2(3) ?
C9 C8 C13 C12 . . . . -1.5(3) ?
C11 C10 O3 C16 . . . . 174.9(2) ?
C11 C12 C13 C8 . . . . 0.2(3) ?
C11 C10 C9 C8 . . . . -0.2(3) ?
C12 C11 C10 O3 . . . . 178.83(19) ?
C12 C11 C10 C9 . . . . -1.0(3) ?
C13 C8 C9 C10 . . . . 1.5(3) ?
C13 C12 C11 O2 . . . . -175.99(19) ?
C13 C12 C11 C10 . . . . 1.0(3) ?
C14 O1 C12 C11 . . . . -179.1(2) ?
C14 O1 C12 C13 . . . . 0.5(3) ?
C15 O2 C11 C10 . . . . 88.3(2) ?
C15 O2 C11 C12 . . . . -94.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3526068
