#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/30/2223082.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_2223082
loop_
_publ_author_name
'Qian, Heng-Yu'
'Qu, Da-Ping'
_publ_section_title
;(E)-N'-(3,5-Dibromo-2-hydroxybenzylidene)-2-nitrobenzohydrazide
 methanol solvate
;
_journal_coeditor_code           HB5053
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2237
_journal_paper_doi               10.1107/S160053680903311X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H9 Br2 N3 O4, CH4 O'
_chemical_formula_moiety         'C14 H9 Br2 N3 O4, CH4 O'
_chemical_formula_sum            'C15 H13 Br2 N3 O5'
_chemical_formula_weight         475.10
_chemical_name_systematic
;
(E)-N'-(3,5-Dibromo-2-hydroxybenzylidene)-2-nitrobenzohydrazide
methanol solvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 110.974(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.9810(10)
_cell_length_b                   10.054(2)
_cell_length_c                   19.746(2)
_cell_measurement_reflns_used    3081
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.7
_cell_volume                     3518.6(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10461
_diffrn_reflns_theta_full        26.90
_diffrn_reflns_theta_max         26.90
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.639
_exptl_absorpt_correction_T_max  0.524
_exptl_absorpt_correction_T_min  0.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.655
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0356
_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)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                2670
_reflns_number_total             3784
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5053.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223082
_cod_database_fobs_code          2223082
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'
'-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 0.07056(2) 0.15611(4) 0.382792(19) 0.05768(14) Uani d . 1 . .
Br Br2 0.14655(2) 0.69346(4) 0.365230(19) 0.06064(15) Uani d . 1 . .
O O1 0.16461(14) 0.1962(2) 0.53986(11) 0.0507(6) Uani d . 1 . .
H H1 0.1901 0.2081 0.5828 0.076 Uiso calc R 1 . .
O O2 0.26477(13) 0.1296(2) 0.74915(11) 0.0556(6) Uani d . 1 . .
O O3 0.42343(15) 0.0570(3) 0.78985(13) 0.0758(8) Uani d . 1 . .
O O4 0.43759(18) -0.0577(3) 0.88592(14) 0.0873(9) Uani d . 1 . .
O O5 0.12161(14) 0.0782(2) 0.74447(13) 0.0640(7) Uani d . 1 . .
H H5 0.1605 0.1003 0.7384 0.096 Uiso calc R 1 . .
N N1 0.25316(14) 0.3244(2) 0.65150(13) 0.0403(6) Uani d . 1 . .
N N2 0.30067(15) 0.3314(2) 0.72253(13) 0.0421(6) Uani d D 1 . .
N N3 0.42213(15) 0.0446(3) 0.85052(15) 0.0526(7) Uani d . 1 . .
C C1 0.20261(16) 0.4236(3) 0.53512(14) 0.0357(6) Uani d . 1 . .
C C2 0.16312(16) 0.3082(3) 0.50269(15) 0.0369(7) Uani d . 1 . .
C C3 0.12163(17) 0.3109(3) 0.42817(15) 0.0391(7) Uani d . 1 . .
C C4 0.11755(16) 0.4237(3) 0.38783(15) 0.0429(7) Uani d . 1 . .
H H4 0.0893 0.4242 0.3384 0.052 Uiso calc R 1 . .
C C5 0.15566(17) 0.5361(3) 0.42122(15) 0.0422(7) Uani d . 1 . .
C C6 0.19789(16) 0.5366(3) 0.49391(15) 0.0405(7) Uani d . 1 . .
H H6 0.2235 0.6133 0.5156 0.049 Uiso calc R 1 . .
C C7 0.24867(16) 0.4255(3) 0.61175(15) 0.0390(7) Uani d . 1 . .
H H7 0.2753 0.5021 0.6320 0.047 Uiso calc R 1 . .
C C8 0.30280(16) 0.2312(3) 0.76752(16) 0.0384(7) Uani d . 1 . .
C C9 0.35228(16) 0.2548(3) 0.84468(15) 0.0365(7) Uani d . 1 . .
C C10 0.40432(17) 0.1623(3) 0.88545(15) 0.0391(7) Uani d . 1 . .
C C11 0.4444(2) 0.1791(3) 0.95794(16) 0.0517(9) Uani d . 1 . .
H H11 0.4787 0.1150 0.9840 0.062 Uiso calc R 1 . .
C C12 0.4331(2) 0.2913(4) 0.99107(18) 0.0608(10) Uani d . 1 . .
H H12 0.4601 0.3039 1.0402 0.073 Uiso calc R 1 . .
C C13 0.3827(2) 0.3856(4) 0.95328(18) 0.0622(10) Uani d . 1 . .
H H13 0.3756 0.4621 0.9766 0.075 Uiso calc R 1 . .
C C14 0.34200(19) 0.3670(3) 0.87998(16) 0.0494(8) Uani d . 1 . .
H H14 0.3074 0.4312 0.8544 0.059 Uiso calc R 1 . .
C C15 0.0603(2) 0.1292(4) 0.6894(2) 0.0898(15) Uani d . 1 . .
H H15A 0.0148 0.0934 0.6928 0.135 Uiso calc R 1 . .
H H15B 0.0634 0.1056 0.6435 0.135 Uiso calc R 1 . .
H H15C 0.0599 0.2243 0.6937 0.135 Uiso calc R 1 . .
H H2 0.3299(18) 0.403(2) 0.7369(19) 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
C2 O1 H1 . . 109.5 ?
C15 O5 H5 . . 109.5 ?
C7 N1 N2 . . 117.7(2) ?
C8 N2 N1 . . 119.6(2) ?
C8 N2 H2 . . 122(2) ?
N1 N2 H2 . . 118(2) ?
O3 N3 O4 . . 124.6(3) ?
O3 N3 C10 . . 118.0(3) ?
O4 N3 C10 . . 117.3(3) ?
C6 C1 C2 . . 120.0(3) ?
C6 C1 C7 . . 119.4(3) ?
C2 C1 C7 . . 120.7(3) ?
O1 C2 C3 . . 119.1(3) ?
O1 C2 C1 . . 122.8(2) ?
C3 C2 C1 . . 118.1(3) ?
C4 C3 C2 . . 121.4(3) ?
C4 C3 Br1 . . 119.6(2) ?
C2 C3 Br1 . . 119.0(2) ?
C3 C4 C5 . . 119.3(3) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C6 C5 C4 . . 121.0(3) ?
C6 C5 Br2 . . 120.2(2) ?
C4 C5 Br2 . . 118.8(2) ?
C5 C6 C1 . . 120.3(3) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
N1 C7 C1 . . 121.1(3) ?
N1 C7 H7 . . 119.5 ?
C1 C7 H7 . . 119.5 ?
O2 C8 N2 . . 123.8(3) ?
O2 C8 C9 . . 121.4(3) ?
N2 C8 C9 . . 114.6(3) ?
C14 C9 C10 . . 117.2(3) ?
C14 C9 C8 . . 119.7(3) ?
C10 C9 C8 . . 122.9(3) ?
C11 C10 C9 . . 122.6(3) ?
C11 C10 N3 . . 117.0(3) ?
C9 C10 N3 . . 120.3(3) ?
C12 C11 C10 . . 118.7(3) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C11 C12 C13 . . 121.0(3) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C12 C13 C14 . . 119.8(3) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C9 C14 C13 . . 120.8(3) ?
C9 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
O5 C15 H15A . . 109.5 ?
O5 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O5 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 . 1.882(3) ?
Br2 C5 . 1.902(3) ?
O1 C2 . 1.338(3) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.228(4) ?
O3 N3 . 1.214(3) ?
O4 N3 . 1.218(4) ?
O5 C15 . 1.376(4) ?
O5 H5 . 0.8200 ?
N1 C7 . 1.269(4) ?
N1 N2 . 1.371(3) ?
N2 C8 . 1.335(4) ?
N2 H2 . 0.893(10) ?
N3 C10 . 1.469(4) ?
C1 C6 . 1.382(4) ?
C1 C2 . 1.405(4) ?
C1 C7 . 1.452(4) ?
C2 C3 . 1.399(4) ?
C3 C4 . 1.372(4) ?
C4 C5 . 1.377(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.371(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.495(4) ?
C9 C14 . 1.376(5) ?
C9 C10 . 1.385(4) ?
C10 C11 . 1.370(4) ?
C11 C12 . 1.359(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.364(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.388(4) ?
C13 H13 . 0.9300 ?
C14 H14 . 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
O1 H1 N1 . 0.82 1.87 2.587(3) 146
O5 H5 O2 . 0.82 1.94 2.735(4) 165
N2 H2 O5 4_556 0.893(10) 1.958(13) 2.840(3) 169(4)
