#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229084.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_2229084
loop_
_publ_author_name
'Li, Tian-Yi'
'Qu, Yue-Gang'
_publ_section_title
;
 3-Chloro-N'-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide
 methanol monosolvate
;
_journal_coeditor_code           HG2785
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o330
_journal_paper_doi               10.1107/S1600536811000742
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H9 Br2 Cl N2 O2, C H4 O'
_chemical_formula_moiety         'C14 H9 Br2 Cl N2 O2, C H4 O'
_chemical_formula_sum            'C15 H13 Br2 Cl N2 O3'
_chemical_formula_weight         464.54
_chemical_name_systematic
;
3-Chloro-N'-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide methanol
monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.634(3)
_cell_angle_beta                 110.952(3)
_cell_angle_gamma                99.392(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8560(18)
_cell_length_b                   9.3810(19)
_cell_length_c                   11.205(2)
_cell_measurement_reflns_used    2168
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.5
_cell_volume                     845.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type
;
Bruker APEXII CCD area-detector
;
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7213
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.968
_exptl_absorpt_correction_T_max  0.4855
_exptl_absorpt_correction_T_min  0.4683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.707
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0441
_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)+(0.0500P)²+0.0441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                2423
_reflns_number_total             3504
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2785.cif
_cod_data_source_block           I
_cod_database_code               2229084
_cod_database_fobs_code          2229084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.29523(6) 0.00200(5) 1.38779(5) 0.0684(2) Uani d . 1 . .
Br Br2 -0.39950(6) -0.16848(6) 1.18451(5) 0.0754(2) Uani d . 1 . .
Cl Cl1 -0.12376(13) 0.68386(11) 0.50390(9) 0.0538(3) Uani d . 1 . .
N N1 0.0467(4) 0.2942(3) 0.9916(3) 0.0375(7) Uani d . 1 . .
N N2 0.0405(4) 0.3784(3) 0.8978(3) 0.0386(7) Uani d D 1 . .
O O1 0.2266(3) 0.1922(3) 1.1849(3) 0.0496(7) Uani d . 1 . .
H H1 0.2078 0.2450 1.1295 0.074 Uiso calc R 1 . .
O O2 0.3090(3) 0.4803(3) 1.0115(3) 0.0533(7) Uani d . 1 . .
O O3 0.2945(3) 0.6052(3) 0.2405(3) 0.0578(8) Uani d . 1 . .
H H3 0.3060 0.5530 0.1826 0.087 Uiso calc R 1 . .
C C1 -0.0709(5) 0.1171(4) 1.0859(3) 0.0338(8) Uani d . 1 . .
C C2 0.0834(4) 0.1111(4) 1.1785(3) 0.0346(8) Uani d . 1 . .
C C3 0.0872(4) 0.0173(4) 1.2683(3) 0.0388(8) Uani d . 1 . .
C C4 -0.0538(5) -0.0650(4) 1.2702(3) 0.0439(9) Uani d . 1 . .
H H4 -0.0484 -0.1259 1.3316 0.053 Uiso calc R 1 . .
C C5 -0.2040(5) -0.0563(4) 1.1797(4) 0.0420(9) Uani d . 1 . .
C C6 -0.2136(5) 0.0304(4) 1.0871(3) 0.0392(8) Uani d . 1 . .
H H6 -0.3162 0.0315 1.0246 0.047 Uiso calc R 1 . .
C C7 -0.0839(4) 0.2091(4) 0.9867(3) 0.0356(8) Uani d . 1 . .
H H7 -0.1856 0.2058 0.9212 0.043 Uiso calc R 1 . .
C C8 0.1846(4) 0.4709(4) 0.9153(3) 0.0349(8) Uani d . 1 . .
C C9 0.1854(4) 0.5574(4) 0.8114(3) 0.0341(8) Uani d . 1 . .
C C10 0.0427(4) 0.5745(3) 0.7138(3) 0.0349(8) Uani d . 1 . .
H H10 -0.0608 0.5274 0.7088 0.042 Uiso calc R 1 . .
C C11 0.0560(5) 0.6615(4) 0.6248(3) 0.0388(8) Uani d . 1 . .
C C12 0.2061(5) 0.7299(4) 0.6284(4) 0.0503(10) Uani d . 1 . .
H H12 0.2126 0.7875 0.5667 0.060 Uiso calc R 1 . .
C C13 0.3475(5) 0.7129(5) 0.7242(4) 0.0560(11) Uani d . 1 . .
H H13 0.4504 0.7598 0.7279 0.067 Uiso calc R 1 . .
C C14 0.3379(5) 0.6269(4) 0.8146(4) 0.0459(9) Uani d . 1 . .
H H14 0.4345 0.6151 0.8785 0.055 Uiso calc R 1 . .
C C15 0.4103(6) 0.5924(6) 0.3610(4) 0.0718(14) Uani d . 1 . .
H H15A 0.5198 0.6338 0.3671 0.108 Uiso calc R 1 . .
H H15B 0.4020 0.4907 0.3691 0.108 Uiso calc R 1 . .
H H15C 0.3882 0.6438 0.4293 0.108 Uiso calc R 1 . .
H H2 -0.060(3) 0.383(5) 0.842(4) 0.086 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'
Cl Cl 0.1484 0.1585 '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 . . 120.4(3) ?
C8 N2 N1 . . 115.9(3) ?
C8 N2 H2 . . 125(3) ?
N1 N2 H2 . . 118(3) ?
C2 O1 H1 . . 109.5 ?
C15 O3 H3 . . 109.5 ?
C6 C1 C2 . . 119.2(3) ?
C6 C1 C7 . . 119.5(3) ?
C2 C1 C7 . . 121.3(3) ?
O1 C2 C3 . . 118.8(3) ?
O1 C2 C1 . . 123.0(3) ?
C3 C2 C1 . . 118.3(3) ?
C4 C3 C2 . . 122.0(3) ?
C4 C3 Br1 . . 119.6(3) ?
C2 C3 Br1 . . 118.4(3) ?
C3 C4 C5 . . 118.8(3) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
C6 C5 C4 . . 121.2(3) ?
C6 C5 Br2 . . 120.2(3) ?
C4 C5 Br2 . . 118.6(3) ?
C5 C6 C1 . . 120.4(4) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
N1 C7 C1 . . 118.7(3) ?
N1 C7 H7 . . 120.6 ?
C1 C7 H7 . . 120.6 ?
O2 C8 N2 . . 121.2(3) ?
O2 C8 C9 . . 121.3(3) ?
N2 C8 C9 . . 117.4(3) ?
C14 C9 C10 . . 118.8(3) ?
C14 C9 C8 . . 117.5(3) ?
C10 C9 C8 . . 123.7(3) ?
C11 C10 C9 . . 119.4(3) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C12 C11 C10 . . 121.7(3) ?
C12 C11 Cl1 . . 119.3(3) ?
C10 C11 Cl1 . . 119.0(3) ?
C11 C12 C13 . . 119.2(3) ?
C11 C12 H12 . . 120.4 ?
C13 C12 H12 . . 120.4 ?
C12 C13 C14 . . 120.4(4) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 C9 . . 120.5(4) ?
C13 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
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 . 1.889(3) ?
Br2 C5 . 1.895(4) ?
Cl1 C11 . 1.743(4) ?
N1 C7 . 1.274(4) ?
N1 N2 . 1.367(4) ?
N2 C8 . 1.359(5) ?
N2 H2 . 0.90(4) ?
O1 C2 . 1.342(4) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.218(4) ?
O3 C15 . 1.404(5) ?
O3 H3 . 0.8200 ?
C1 C6 . 1.392(5) ?
C1 C2 . 1.403(5) ?
C1 C7 . 1.457(4) ?
C2 C3 . 1.396(5) ?
C3 C4 . 1.366(5) ?
C4 C5 . 1.375(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.368(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.484(4) ?
C9 C14 . 1.387(5) ?
C9 C10 . 1.389(4) ?
C10 C11 . 1.374(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.363(6) ?
C12 C13 . 1.373(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.373(5) ?
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
N2 H2 O3 2_566 0.90(4) 1.976(17) 2.852(4) 165(5)
O3 H3 O2 1_554 0.82 1.98 2.769(4) 161
O1 H1 N1 . 0.82 1.85 2.566(4) 146
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656468
