#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225383.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_2225383
loop_
_publ_author_name
'Su, Yong-Qing'
'Li, Cong'
'Wang, Ping'
_publ_section_title
;
 (E)-N'-(3,5-Dibromo-2-hydroxybenzylidene)nicotinohydrazide
;
_journal_coeditor_code           SU2163
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o670
_journal_paper_doi               10.1107/S1600536810006276
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H9 Br2 N3 O2'
_chemical_formula_moiety         'C13 H9 Br2 N3 O2'
_chemical_formula_sum            'C13 H9 Br2 N3 O2'
_chemical_formula_weight         399.05
_chemical_name_systematic
;
(E)-N'-(3,5-Dibromo-2-hydroxybenzylidene)nicotinohydrazide
;
_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                 92.194(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.013(4)
_cell_length_b                   8.091(2)
_cell_length_c                   10.153(3)
_cell_measurement_reflns_used    2084
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2.4
_cell_volume                     1396.6(6)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       '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  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8024
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.20
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.808
_exptl_absorpt_correction_T_max  0.3896
_exptl_absorpt_correction_T_min  0.3485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.686
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                1933
_reflns_number_total             3023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2163.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225383
_cod_database_fobs_code          2225383
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.38611(2) 1.15620(7) 0.38681(5) 0.0731(2) Uani d . 1 . .
Br Br2 0.44353(2) 0.85756(6) 0.88313(4) 0.06341(18) Uani d . 1 . .
N N1 0.11733(17) 0.8462(3) 0.5380(3) 0.0393(7) Uani d . 1 . .
N N2 0.04257(16) 0.7852(4) 0.5483(3) 0.0402(7) Uani d D 1 . .
N N3 -0.16645(18) 0.5160(4) 0.5780(3) 0.0501(8) Uani d . 1 . .
O O1 0.22622(14) 1.0061(3) 0.4163(2) 0.0514(7) Uani d . 1 . .
H H1 0.1820 0.9696 0.4270 0.077 Uiso calc R 1 . .
O O2 0.01730(14) 0.8169(3) 0.3293(2) 0.0508(7) Uani d . 1 . .
C C1 0.2459(2) 0.8814(4) 0.6310(3) 0.0383(8) Uani d . 1 . .
C C2 0.27257(19) 0.9725(4) 0.5231(3) 0.0377(8) Uani d . 1 . .
C C3 0.3494(2) 1.0292(4) 0.5283(3) 0.0437(9) Uani d . 1 . .
C C4 0.4001(2) 0.9964(4) 0.6347(3) 0.0455(9) Uani d . 1 . .
H H4 0.4512 1.0374 0.6373 0.055 Uiso calc R 1 . .
C C5 0.3737(2) 0.9026(4) 0.7363(3) 0.0403(8) Uani d . 1 . .
C C6 0.2980(2) 0.8450(4) 0.7371(3) 0.0430(9) Uani d . 1 . .
H H6 0.2813 0.7823 0.8076 0.052 Uiso calc R 1 . .
C C7 0.1655(2) 0.8224(4) 0.6360(3) 0.0396(8) Uani d . 1 . .
H H7 0.1490 0.7673 0.7104 0.048 Uiso calc R 1 . .
C C8 -0.00388(19) 0.7712(4) 0.4372(3) 0.0366(8) Uani d . 1 . .
C C9 -0.08166(19) 0.6936(4) 0.4557(3) 0.0358(8) Uani d . 1 . .
C C10 -0.1424(2) 0.7215(5) 0.3642(4) 0.0492(9) Uani d . 1 . .
H H10 -0.1347 0.7889 0.2917 0.059 Uiso calc R 1 . .
C C11 -0.2145(2) 0.6488(5) 0.3811(4) 0.0541(11) Uani d . 1 . .
H H11 -0.2561 0.6666 0.3207 0.065 Uiso calc R 1 . .
C C12 -0.2236(2) 0.5493(5) 0.4894(4) 0.0510(10) Uani d . 1 . .
H H12 -0.2727 0.5025 0.5011 0.061 Uiso calc R 1 . .
C C13 -0.0972(2) 0.5869(4) 0.5595(3) 0.0417(9) Uani d . 1 . .
H H13 -0.0563 0.5637 0.6200 0.050 Uiso calc R 1 . .
H H2 0.024(2) 0.764(6) 0.629(2) 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'
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
C7 N1 N2 . . 117.1(3) ?
C8 N2 N1 . . 118.6(3) ?
C8 N2 H2 . . 122(3) ?
N1 N2 H2 . . 119(3) ?
C12 N3 C13 . . 116.5(3) ?
C2 O1 H1 . . 109.5 ?
C6 C1 C2 . . 119.6(3) ?
C6 C1 C7 . . 118.3(3) ?
C2 C1 C7 . . 122.1(3) ?
O1 C2 C3 . . 119.2(3) ?
O1 C2 C1 . . 122.4(3) ?
C3 C2 C1 . . 118.4(3) ?
C4 C3 C2 . . 121.7(3) ?
C4 C3 Br1 . . 118.9(3) ?
C2 C3 Br1 . . 119.4(3) ?
C5 C4 C3 . . 118.9(3) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 121.9(3) ?
C4 C5 Br2 . . 118.9(3) ?
C6 C5 Br2 . . 119.2(3) ?
C5 C6 C1 . . 119.4(3) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
N1 C7 C1 . . 120.0(3) ?
N1 C7 H7 . . 120.0 ?
C1 C7 H7 . . 120.0 ?
O2 C8 N2 . . 122.5(3) ?
O2 C8 C9 . . 122.4(3) ?
N2 C8 C9 . . 115.1(3) ?
C10 C9 C13 . . 116.7(3) ?
C10 C9 C8 . . 119.6(3) ?
C13 C9 C8 . . 123.6(3) ?
C11 C10 C9 . . 119.6(4) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 118.5(4) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
N3 C12 C11 . . 124.0(4) ?
N3 C12 H12 . . 118.0 ?
C11 C12 H12 . . 118.0 ?
N3 C13 C9 . . 124.6(3) ?
N3 C13 H13 . . 117.7 ?
C9 C13 H13 . . 117.7 ?
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 . 1.892(4) ?
Br2 C5 . 1.905(3) ?
N1 C7 . 1.278(4) ?
N1 N2 . 1.372(4) ?
N2 C8 . 1.357(4) ?
N2 H2 . 0.901(10) ?
N3 C12 . 1.326(4) ?
N3 C13 . 1.330(4) ?
O1 C2 . 1.344(4) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.223(4) ?
C1 C6 . 1.401(5) ?
C1 C2 . 1.409(5) ?
C1 C7 . 1.452(5) ?
C2 C3 . 1.384(5) ?
C3 C4 . 1.382(4) ?
C4 C5 . 1.370(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.371(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.483(5) ?
C9 C10 . 1.381(5) ?
C9 C13 . 1.396(5) ?
C10 C11 . 1.377(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.376(5) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
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
O1 H1 N1 . 0.82 1.89 2.609(4) 146
N2 H2 O2 4_576 0.91(2) 2.14(2) 3.017(4) 162(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12272149
