#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222328.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_2222328
loop_
_publ_author_name
'Cao, Guo-Biao'
'Lu, Xu-Hui'
_publ_section_title
(E)-N'-(3,5-Dibromo-2-hydroxybenzylidene)-2-methoxybenzohydrazide
_journal_coeditor_code           HB5004
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1587
_journal_paper_doi               10.1107/S1600536809022168
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H12 Br2 N2 O3'
_chemical_formula_moiety         'C15 H12 Br2 N2 O3'
_chemical_formula_sum            'C15 H12 Br2 N2 O3'
_chemical_formula_weight         428.09
_chemical_name_systematic
;
(E)-N'-(3,5-Dibromo-2-hydroxybenzylidene)-2-methoxybenzohydrazide
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 96.476(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8860(10)
_cell_length_b                   12.956(2)
_cell_length_c                   10.965(2)
_cell_measurement_reflns_used    2250
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.4
_cell_volume                     1536.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4623
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.289
_exptl_absorpt_correction_T_max  0.329
_exptl_absorpt_correction_T_min  0.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.620
_refine_ls_abs_structure_details 'Flack (1983), 531 Friedel pairs'
_refine_ls_abs_structure_Flack   0.513(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0877P)²+0.6851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                1992
_reflns_number_total             2208
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5004.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2222328
_cod_database_fobs_code          2222328
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'
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 0.39963(8) -0.26669(6) -0.15520(7) 0.0501(2) Uani d . 1 . .
Br Br2 0.48191(8) -0.46448(6) 0.30371(8) 0.0556(3) Uani d . 1 . .
O O1 0.5231(5) -0.0896(4) -0.0108(4) 0.0388(11) Uani d . 1 . .
H H1 0.5797 -0.0514 0.0166 0.058 Uiso calc R 1 . .
O O2 0.6295(7) 0.1701(5) 0.0431(5) 0.0548(16) Uani d . 1 . .
O O3 0.7666(6) 0.2128(4) 0.4081(5) 0.0466(14) Uani d . 1 . .
N N1 0.6150(6) 0.0066(5) 0.1793(5) 0.0341(12) Uani d . 1 . .
N N2 0.6578(6) 0.0982(4) 0.2312(5) 0.0360(12) Uani d D 1 . .
C C1 0.5608(6) -0.1684(5) 0.1883(6) 0.0300(13) Uani d . 1 . .
C C2 0.5188(6) -0.1713(5) 0.0627(6) 0.0306(13) Uani d . 1 . .
C C3 0.4675(7) -0.2629(5) 0.0147(7) 0.0351(14) Uani d . 1 . .
C C4 0.4612(7) -0.3510(5) 0.0854(8) 0.0389(15) Uani d . 1 . .
H H4 0.4296 -0.4122 0.0504 0.047 Uiso calc R 1 . .
C C5 0.5026(7) -0.3458(5) 0.2081(7) 0.0369(15) Uani d . 1 . .
C C6 0.5533(7) -0.2572(5) 0.2625(8) 0.0360(16) Uani d . 1 . .
H H6 0.5818 -0.2559 0.3456 0.043 Uiso calc R 1 . .
C C7 0.6101(7) -0.0736(5) 0.2472(6) 0.0343(14) Uani d . 1 . .
H H7 0.6369 -0.0714 0.3307 0.041 Uiso calc R 1 . .
C C8 0.6631(7) 0.1797(6) 0.1527(6) 0.0332(14) Uani d . 1 . .
C C9 0.7136(7) 0.2793(5) 0.2082(7) 0.0354(15) Uani d . 1 . .
C C10 0.7100(8) 0.3626(6) 0.1268(8) 0.0458(18) Uani d . 1 . .
H H10 0.6764 0.3535 0.0458 0.055 Uiso calc R 1 . .
C C11 0.7548(10) 0.4567(7) 0.1642(12) 0.063(3) Uani d . 1 . .
H H11 0.7503 0.5115 0.1090 0.076 Uiso calc R 1 . .
C C12 0.8069(9) 0.4715(7) 0.2835(11) 0.059(2) Uani d . 1 . .
H H12 0.8380 0.5358 0.3088 0.071 Uiso calc R 1 . .
C C13 0.8126(8) 0.3906(7) 0.3647(9) 0.052(2) Uani d . 1 . .
H H13 0.8486 0.4003 0.4449 0.062 Uiso calc R 1 . .
C C14 0.7652(7) 0.2940(6) 0.3286(7) 0.0386(15) Uani d . 1 . .
C C15 0.8276(10) 0.2211(8) 0.5282(8) 0.062(3) Uani d . 1 . .
H H15A 0.9101 0.2462 0.5248 0.093 Uiso calc R 1 . .
H H15B 0.8309 0.1545 0.5668 0.093 Uiso calc R 1 . .
H H15C 0.7833 0.2682 0.5748 0.093 Uiso calc R 1 . .
H H2 0.692(9) 0.097(9) 0.310(3) 0.080 Uiso d D 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'
Br Br -0.2901 2.4595 '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'
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
C2 O1 H1 . . 109.5 ?
C14 O3 C15 . . 120.5(7) ?
C7 N1 N2 . . 119.5(6) ?
C8 N2 N1 . . 116.3(5) ?
C8 N2 H2 . . 125(7) ?
N1 N2 H2 . . 118(7) ?
C2 C1 C6 . . 120.5(6) ?
C2 C1 C7 . . 121.3(6) ?
C6 C1 C7 . . 118.1(6) ?
O1 C2 C3 . . 119.2(6) ?
O1 C2 C1 . . 122.8(6) ?
C3 C2 C1 . . 117.9(6) ?
C4 C3 C2 . . 122.3(7) ?
C4 C3 Br1 . . 118.8(5) ?
C2 C3 Br1 . . 118.9(5) ?
C5 C4 C3 . . 118.5(6) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
C4 C5 C6 . . 122.4(6) ?
C4 C5 Br2 . . 117.3(5) ?
C6 C5 Br2 . . 120.3(6) ?
C5 C6 C1 . . 118.3(7) ?
C5 C6 H6 . . 120.9 ?
C1 C6 H6 . . 120.9 ?
N1 C7 C1 . . 117.5(6) ?
N1 C7 H7 . . 121.3 ?
C1 C7 H7 . . 121.3 ?
O2 C8 N2 . . 120.7(6) ?
O2 C8 C9 . . 122.7(6) ?
N2 C8 C9 . . 116.6(6) ?
C14 C9 C10 . . 118.7(7) ?
C14 C9 C8 . . 126.3(7) ?
C10 C9 C8 . . 114.9(7) ?
C11 C10 C9 . . 121.1(9) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C10 C11 C12 . . 120.3(9) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 119.6(8) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 120.9(9) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
O3 C14 C9 . . 118.4(6) ?
O3 C14 C13 . . 122.2(7) ?
C9 C14 C13 . . 119.4(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 ?
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 C3 . 1.925(7) ?
Br2 C5 . 1.889(7) ?
O1 C2 . 1.335(8) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.222(8) ?
O3 C14 . 1.366(10) ?
O3 C15 . 1.411(11) ?
N1 C7 . 1.282(9) ?
N1 N2 . 1.375(8) ?
N2 C8 . 1.367(9) ?
N2 H2 . 0.90(5) ?
C1 C2 . 1.401(9) ?
C1 C6 . 1.417(9) ?
C1 C7 . 1.461(9) ?
C2 C3 . 1.389(10) ?
C3 C4 . 1.386(11) ?
C4 C5 . 1.372(11) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.379(10) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.504(10) ?
C9 C14 . 1.388(11) ?
C9 C10 . 1.398(11) ?
C10 C11 . 1.359(13) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(17) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.372(14) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.394(10) ?
C13 H13 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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 O3 . 0.90(5) 1.97(9) 2.617(8) 128(9)
O1 H1 N1 . 0.82 1.93 2.535(7) 130
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742598
