#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/14/2221499.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_2221499
loop_
_publ_author_name
'Wei, Yi-Jun'
'Wang, Feng-Wu'
'Zhu, Qi-Yong'
_publ_section_title
;
 3-Bromo-N'-(3,5-dibromo-2-hydroxybenzylidene)benzohydrazide
 methanol solvate
;
_journal_coeditor_code           SJ2587
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o688
_journal_paper_doi               10.1107/S1600536809007466
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H9 Br3 N2 O2, C H4 O'
_chemical_formula_moiety         'C14 H9 Br3 N2 O2, C H4 O'
_chemical_formula_sum            'C15 H13 Br3 N2 O3'
_chemical_formula_weight         509.00
_chemical_name_systematic
;
 ?
;
_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                95.043(2)
_cell_angle_beta                 111.048(2)
_cell_angle_gamma                99.584(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9000(10)
_cell_length_b                   9.3660(10)
_cell_length_c                   11.392(2)
_cell_measurement_reflns_used    1965
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.5
_cell_volume                     862.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_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 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5016
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.029
_exptl_absorpt_correction_T_max  0.245
_exptl_absorpt_correction_T_min  0.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.611
_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         3606
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0368P)²+0.2522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0843
_reflns_number_gt                2582
_reflns_number_total             3606
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2587.cif
_cod_data_source_block           I
_cod_database_code               2221499
_cod_database_fobs_code          2221499
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 0.70334(5) 1.00574(5) -0.37638(4) 0.07063(16) Uani d . 1 . .
Br Br2 1.39490(6) 1.16831(6) -0.18075(5) 0.08319(19) Uani d . 1 . .
Br Br3 1.13101(5) 0.31103(4) 0.49994(3) 0.05564(13) Uani d . 1 . .
O O1 0.7708(3) 0.8094(3) -0.1804(2) 0.0524(6) Uani d . 1 . .
H H1 0.7891 0.7546 -0.1269 0.079 Uiso calc R 1 . .
O O2 0.6880(3) 0.5145(3) -0.0140(2) 0.0564(7) Uani d . 1 . .
O O3 0.7124(3) 0.4000(3) 0.7628(2) 0.0634(7) Uani d . 1 . .
H H3 0.6886 0.4388 0.8192 0.095 Uiso calc R 1 . .
N N1 0.9495(3) 0.7027(3) 0.0069(2) 0.0402(6) Uani d . 1 . .
N N2 0.9553(4) 0.6172(3) 0.0991(3) 0.0410(6) Uani d D 1 . .
C C1 1.0672(4) 0.8813(3) -0.0850(3) 0.0351(7) Uani d . 1 . .
C C2 0.9137(4) 0.8887(4) -0.1748(3) 0.0378(7) Uani d . 1 . .
C C3 0.9096(4) 0.9860(4) -0.2607(3) 0.0425(8) Uani d . 1 . .
C C4 1.0505(4) 1.0671(4) -0.2633(3) 0.0449(8) Uani d . 1 . .
H H4 1.0450 1.1288 -0.3236 0.054 Uiso calc R 1 . .
C C5 1.2002(4) 1.0569(4) -0.1762(3) 0.0460(8) Uani d . 1 . .
C C6 1.2101(4) 0.9668(4) -0.0856(3) 0.0424(8) Uani d . 1 . .
H H6 1.3121 0.9632 -0.0251 0.051 Uiso calc R 1 . .
C C7 1.0795(4) 0.7865(3) 0.0117(3) 0.0389(8) Uani d . 1 . .
H H7 1.1807 0.7877 0.0755 0.047 Uiso calc R 1 . .
C C8 0.8112(4) 0.5247(4) 0.0818(3) 0.0388(7) Uani d . 1 . .
C C9 0.8101(4) 0.4374(3) 0.1852(3) 0.0365(7) Uani d . 1 . .
C C10 0.6573(4) 0.3690(4) 0.1800(3) 0.0487(9) Uani d . 1 . .
H H10 0.5620 0.3809 0.1160 0.058 Uiso calc R 1 . .
C C11 0.6468(5) 0.2827(5) 0.2705(4) 0.0607(11) Uani d . 1 . .
H H11 0.5442 0.2361 0.2670 0.073 Uiso calc R 1 . .
C C12 0.7878(5) 0.2654(4) 0.3657(4) 0.0538(10) Uani d . 1 . .
H H12 0.7811 0.2077 0.4268 0.065 Uiso calc R 1 . .
C C13 0.9373(4) 0.3341(4) 0.3692(3) 0.0407(8) Uani d . 1 . .
C C14 0.9518(4) 0.4212(3) 0.2807(3) 0.0375(7) Uani d . 1 . .
H H14 1.0550 0.4679 0.2853 0.045 Uiso calc R 1 . .
C C15 0.5947(6) 0.4070(6) 0.6437(4) 0.0784(14) Uani d . 1 . .
H H15A 0.5748 0.5045 0.6420 0.118 Uiso calc R 1 . .
H H15B 0.4939 0.3389 0.6291 0.118 Uiso calc R 1 . .
H H15C 0.6346 0.3822 0.5784 0.118 Uiso calc R 1 . .
H H2 1.054(3) 0.617(5) 0.159(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 ?
C15 O3 H3 . . 109.5 ?
C7 N1 N2 . . 120.2(3) ?
C8 N2 N1 . . 115.8(3) ?
C8 N2 H2 . . 125(3) ?
N1 N2 H2 . . 118(3) ?
C6 C1 C2 . . 120.0(3) ?
C6 C1 C7 . . 119.1(3) ?
C2 C1 C7 . . 120.8(3) ?
O1 C2 C3 . . 118.5(3) ?
O1 C2 C1 . . 123.4(3) ?
C3 C2 C1 . . 118.1(3) ?
C4 C3 C2 . . 121.7(3) ?
C4 C3 Br1 . . 119.5(2) ?
C2 C3 Br1 . . 118.8(3) ?
C3 C4 C5 . . 119.5(3) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 Br2 . . 119.4(3) ?
C6 C5 Br2 . . 119.8(3) ?
C5 C6 C1 . . 119.7(3) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N1 C7 C1 . . 118.6(3) ?
N1 C7 H7 . . 120.7 ?
C1 C7 H7 . . 120.7 ?
O2 C8 N2 . . 121.2(3) ?
O2 C8 C9 . . 121.5(3) ?
N2 C8 C9 . . 117.2(3) ?
C14 C9 C10 . . 120.4(3) ?
C14 C9 C8 . . 123.2(3) ?
C10 C9 C8 . . 116.4(3) ?
C9 C10 C11 . . 119.6(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.3(3) ?
C12 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C13 C12 C11 . . 119.0(3) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C12 C13 C14 . . 122.0(3) ?
C12 C13 Br3 . . 119.2(3) ?
C14 C13 Br3 . . 118.8(2) ?
C13 C14 C9 . . 118.6(3) ?
C13 C14 H14 . . 120.7 ?
C9 C14 H14 . . 120.7 ?
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 . 1.886(3) ?
Br2 C5 . 1.889(3) ?
Br3 C13 . 1.891(3) ?
O1 C2 . 1.339(4) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.221(4) ?
O3 C15 . 1.400(4) ?
O3 H3 . 0.8200 ?
N1 C7 . 1.265(4) ?
N1 N2 . 1.367(3) ?
N2 C8 . 1.361(4) ?
N2 H2 . 0.90(3) ?
C1 C6 . 1.388(5) ?
C1 C2 . 1.399(4) ?
C1 C7 . 1.461(4) ?
C2 C3 . 1.390(4) ?
C3 C4 . 1.365(5) ?
C4 C5 . 1.370(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.378(4) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.494(4) ?
C9 C14 . 1.381(4) ?
C9 C10 . 1.381(5) ?
C10 C11 . 1.385(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.378(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.364(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.378(4) ?
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 1.84 2.559(3) 145.1
O3 H3 O2 1_556 0.82 1.97 2.767(4) 163.6
N2 H2 O3 2_766 0.90(3) 1.986(18) 2.848(4) 160(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655749
