#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/08/2210862.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_2210862
loop_
_publ_author_name
'Hui-Yan Liu'
'Hai-Ying Wang'
'Feng Gao'
'Zai-Sheng Lu'
'De-Zhong Niu'
_publ_section_title
(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,5-dimethoxybenzohydrazide
_journal_coeditor_code           AT2133
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5259
_journal_page_last               o5260
_journal_paper_doi               10.1107/S1600536806043534
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H15 Br N2 O4'
_chemical_formula_moiety         'C16 H15 Br N2 O4'
_chemical_formula_sum            'C16 H15 Br N2 O4'
_chemical_formula_weight         379.21
_chemical_name_systematic
;
 (E)-N'-(5-bromo-2-hydroxybenzylidene)-3,5-dimethoxybenzohydrazide
;
_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                 104.483(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.235(2)
_cell_length_b                   15.973(3)
_cell_length_c                   9.2501(16)
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.853
_cell_measurement_theta_min      2.265
_cell_volume                     1607.2(5)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8371
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.579
_exptl_absorpt_correction_T_max  0.7304
_exptl_absorpt_correction_T_min  0.5321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.521
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0397
_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)+(0.0291P)²+1.1980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1590
_reflns_number_total             2824
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2133.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210862
_cod_database_fobs_code          2210862
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
Br Br1 0.42650(5) 1.21539(3) 0.43921(7) 0.0935(3) Uani d . 1
N N1 0.2731(3) 0.83944(19) 0.5746(3) 0.0455(8) Uani d . 1
N N2 0.2183(3) 0.77311(18) 0.4876(3) 0.0473(8) Uani d . 1
H H2 0.1975 0.7780 0.3920 0.057 Uiso calc R 1
O O1 0.4072(3) 0.91282(19) 0.8199(3) 0.0695(8) Uani d . 1
H H1 0.3643 0.8758 0.7718 0.104 Uiso calc R 1
O O2 0.2215(3) 0.69118(15) 0.6869(3) 0.0618(8) Uani d . 1
O O3 0.1522(3) 0.40314(18) 0.4269(4) 0.0813(9) Uani d . 1
O O4 -0.0570(3) 0.5923(2) 0.0727(3) 0.0860(10) Uani d . 1
C C1 0.2843(3) 0.9066(2) 0.5041(4) 0.0459(9) Uani d . 1
H H1A 0.2499 0.9089 0.4017 0.055 Uiso calc R 1
C C2 0.3489(3) 0.9790(2) 0.5788(4) 0.0452(9) Uani d . 1
C C3 0.4088(4) 0.9795(3) 0.7307(5) 0.0528(10) Uani d . 1
C C4 0.4750(4) 1.0498(3) 0.7927(5) 0.0693(13) Uani d . 1
H H4 0.5157 1.0500 0.8935 0.083 Uiso calc R 1
C C5 0.4809(4) 1.1188(3) 0.7066(6) 0.0711(14) Uani d . 1
H H5 0.5260 1.1654 0.7490 0.085 Uiso calc R 1
C C6 0.4200(4) 1.1193(3) 0.5572(6) 0.0616(12) Uani d . 1
C C7 0.3559(4) 1.0501(2) 0.4948(5) 0.0543(11) Uani d . 1
H H7 0.3160 1.0505 0.3938 0.065 Uiso calc R 1
C C8 0.1971(3) 0.7009(2) 0.5513(4) 0.0444(9) Uani d . 1
C C9 0.1422(3) 0.6323(2) 0.4452(4) 0.0450(9) Uani d . 1
C C10 0.1709(3) 0.5511(2) 0.4919(4) 0.0518(10) Uani d . 1
H H10 0.2199 0.5404 0.5871 0.062 Uiso calc R 1
C C11 0.1257(4) 0.4856(3) 0.3954(5) 0.0585(11) Uani d . 1
C C12 0.0503(4) 0.5027(3) 0.2567(5) 0.0662(12) Uani d . 1
H H12 0.0194 0.4587 0.1922 0.079 Uiso calc R 1
C C13 0.0200(4) 0.5836(3) 0.2120(5) 0.0588(11) Uani d . 1
C C14 0.0660(3) 0.6498(3) 0.3057(4) 0.0504(10) Uani d . 1
H H14 0.0463 0.7048 0.2759 0.060 Uiso calc R 1
C C15 0.2308(5) 0.3837(3) 0.5680(6) 0.0841(15) Uani d . 1
H H15A 0.2421 0.3242 0.5767 0.126 Uiso calc R 1
H H15B 0.1946 0.4034 0.6454 0.126 Uiso calc R 1
H H15C 0.3089 0.4104 0.5776 0.126 Uiso calc R 1
C C16 -0.0948(4) 0.6730(3) 0.0213(5) 0.0792(14) Uani d . 1
H H16A -0.1470 0.6696 -0.0780 0.119 Uiso calc R 1
H H16B -0.0239 0.7064 0.0205 0.119 Uiso calc R 1
H H16C -0.1392 0.6982 0.0863 0.119 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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 115.7(3) yes
C8 N2 N1 120.4(3) yes
C8 N2 H2 119.8 ?
N1 N2 H2 119.8 ?
C3 O1 H1 109.5 ?
C11 O3 C15 117.4(3) ?
C13 O4 C16 118.6(3) ?
N1 C1 C2 121.9(3) ?
N1 C1 H1A 119.0 ?
C2 C1 H1A 119.0 ?
C7 C2 C3 118.5(4) ?
C7 C2 C1 118.6(4) ?
C3 C2 C1 122.9(4) ?
O1 C3 C4 118.2(4) ?
O1 C3 C2 122.1(4) ?
C4 C3 C2 119.6(4) ?
C5 C4 C3 120.6(4) ?
C5 C4 H4 119.7 ?
C3 C4 H4 119.7 ?
C4 C5 C6 120.1(4) ?
C4 C5 H5 119.9 ?
C6 C5 H5 119.9 ?
C7 C6 C5 119.7(4) ?
C7 C6 Br1 120.3(4) ?
C5 C6 Br1 120.0(4) ?
C6 C7 C2 121.5(4) ?
C6 C7 H7 119.2 ?
C2 C7 H7 119.2 ?
O2 C8 N2 122.6(3) yes
O2 C8 C9 121.9(3) ?
N2 C8 C9 115.5(3) ?
C10 C9 C14 121.5(4) ?
C10 C9 C8 117.2(3) ?
C14 C9 C8 121.3(3) ?
C9 C10 C11 119.2(4) ?
C9 C10 H10 120.4 ?
C11 C10 H10 120.4 ?
O3 C11 C12 116.2(4) ?
O3 C11 C10 124.4(4) ?
C12 C11 C10 119.4(4) ?
C13 C12 C11 121.0(4) ?
C13 C12 H12 119.5 ?
C11 C12 H12 119.5 ?
O4 C13 C12 115.5(4) ?
O4 C13 C14 124.2(4) ?
C12 C13 C14 120.3(4) ?
C13 C14 C9 118.4(4) ?
C13 C14 H14 120.8 ?
C9 C14 H14 120.8 ?
O3 C15 H15A 109.5 ?
O3 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O3 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
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 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C6 1.895(4) ?
N1 C1 1.278(4) yes
N1 N2 1.379(4) yes
N2 C8 1.343(4) yes
N2 H2 0.8600 ?
O1 C3 1.350(5) ?
O1 H1 0.8200 ?
O2 C8 1.225(4) yes
O3 C11 1.366(5) ?
O3 C15 1.415(5) ?
O4 C13 1.368(5) ?
O4 C16 1.403(5) ?
C1 C2 1.446(5) ?
C1 H1A 0.9300 ?
C2 C7 1.389(5) ?
C2 C3 1.398(5) ?
C3 C4 1.388(5) ?
C4 C5 1.372(6) ?
C4 H4 0.9300 ?
C5 C6 1.380(6) ?
C5 H5 0.9300 ?
C6 C7 1.366(5) ?
C7 H7 0.9300 ?
C8 C9 1.497(5) ?
C9 C10 1.380(5) ?
C9 C14 1.387(5) ?
C10 C11 1.387(5) ?
C10 H10 0.9300 ?
C11 C12 1.376(5) ?
C12 C13 1.373(6) ?
C12 H12 0.9300 ?
C13 C14 1.383(5) ?
C14 H14 0.9300 ?
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
N2 H2 O2 4_575 0.86 2.04 2.848(4) 155.8
C1 H1A O2 4_575 0.93 2.51 3.242(4) 136.0
O1 H1 N1 . 0.82 1.94 2.661(4) 145.6
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655079
