#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/67/2226767.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_2226767
loop_
_publ_author_name
'Saharin, Siti Munirah'
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
_publ_section_title
;
 (E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide
 monohydrate
;
_journal_coeditor_code           BH2299
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2045
_journal_paper_doi               10.1107/S1600536810027856
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 Br N2 O4, H2 O'
_chemical_formula_moiety         'C14 H11 Br N2 O4, H2 O'
_chemical_formula_sum            'C14 H13 Br N2 O5'
_chemical_formula_weight         369.17
_chemical_name_systematic
;
(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,5-dihydroxybenzohydrazide
monohydrate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.1860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5685(3)
_cell_length_b                   8.0532(2)
_cell_length_c                   13.2447(2)
_cell_measurement_reflns_used    3109
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.95
_cell_volume                     1424.44(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9148
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.912
_exptl_absorpt_correction_T_max  0.8446
_exptl_absorpt_correction_T_min  0.2829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.557
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0313
_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)+(0.0328P)²+0.7124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0773
_reflns_number_gt                2183
_reflns_number_total             2579
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2299.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226767
_cod_database_fobs_code          2226767
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 0.54976(2) 0.19522(4) 0.67677(2) 0.05405(13) Uani d . 1 . .
O O1 0.25489(15) 0.4914(3) 0.33122(13) 0.0448(5) Uani d D 1 . .
H H1 0.210(2) 0.542(4) 0.351(2) 0.067 Uiso d D 1 . .
O O8 -0.01522(14) 0.6853(2) 0.34596(12) 0.0375(4) Uani d . 1 . .
O O11 -0.18429(14) 0.9113(2) 0.71231(12) 0.0378(4) Uani d D 1 . .
H H11 -0.1355(18) 0.868(4) 0.749(2) 0.057 Uiso d D 1 . .
O O13 -0.29944(14) 1.0800(2) 0.37286(13) 0.0440(5) Uani d D 1 . .
H H13 -0.285(3) 1.075(4) 0.3181(17) 0.066 Uiso d D 1 . .
N N1 0.15274(14) 0.5993(2) 0.47190(14) 0.0279(4) Uani d . 1 . .
N N2 0.07629(15) 0.6835(2) 0.50575(14) 0.0277(4) Uani d D 1 . .
H H2N 0.088(2) 0.712(3) 0.5686(14) 0.033 Uiso d D 1 . .
C C1 0.31939(19) 0.4270(3) 0.41219(17) 0.0312(5) Uani d . 1 . .
C C2 0.3994(2) 0.3354(3) 0.39071(19) 0.0402(6) Uani d . 1 . .
H H2 0.4072 0.3208 0.3229 0.048 Uiso calc R 1 . .
C C3 0.4676(2) 0.2657(3) 0.4683(2) 0.0391(6) Uani d . 1 . .
H H3 0.5211 0.2037 0.4534 0.047 Uiso calc R 1 . .
C C4 0.45524(18) 0.2895(3) 0.56914(18) 0.0330(6) Uani d . 1 . .
C C5 0.37678(18) 0.3807(3) 0.59223(17) 0.0319(5) Uani d . 1 . .
H H5 0.3701 0.3951 0.6603 0.038 Uiso calc R 1 . .
C C6 0.30662(17) 0.4524(3) 0.51387(16) 0.0278(5) Uani d . 1 . .
C C7 0.22369(18) 0.5450(3) 0.54062(17) 0.0300(5) Uani d . 1 . .
H H7 0.2219 0.5656 0.6094 0.036 Uiso calc R 1 . .
C C8 -0.00598(18) 0.7237(3) 0.43815(16) 0.0266(5) Uani d . 1 . .
C C9 -0.08615(17) 0.8158(3) 0.47789(16) 0.0248(5) Uani d . 1 . .
C C10 -0.09485(18) 0.8153(3) 0.58150(16) 0.0274(5) Uani d . 1 . .
H H10 -0.0499 0.7559 0.6293 0.033 Uiso calc R 1 . .
C C11 -0.17126(17) 0.9044(3) 0.61131(16) 0.0276(5) Uani d . 1 . .
C C12 -0.23974(18) 0.9932(3) 0.54147(17) 0.0303(5) Uani d . 1 . .
H H12 -0.2908 1.0530 0.5632 0.036 Uiso calc R 1 . .
C C13 -0.23079(18) 0.9912(3) 0.43882(16) 0.0291(5) Uani d . 1 . .
C C14 -0.15405(17) 0.9038(3) 0.40695(16) 0.0283(5) Uani d . 1 . .
H H14 -0.1479 0.9040 0.3381 0.034 Uiso calc R 1 . .
O O2 0.12746(16) 0.7432(3) 0.72574(13) 0.0428(5) Uani d D 1 . .
H H2A 0.091(2) 0.772(4) 0.764(2) 0.064 Uiso d D 1 . .
H H2B 0.153(3) 0.656(3) 0.750(2) 0.064 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
C1 O1 H1 . . 110(2) ?
C11 O11 H11 . . 109(2) ?
C13 O13 H13 . . 108(3) ?
C7 N1 N2 . . 116.85(18) ?
C8 N2 N1 . . 119.13(18) ?
C8 N2 H2N . . 125.0(18) ?
N1 N2 H2N . . 115.7(18) ?
O1 C1 C2 . . 117.4(2) ?
O1 C1 C6 . . 122.0(2) ?
C2 C1 C6 . . 120.6(2) ?
C3 C2 C1 . . 120.9(2) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 118.8(2) ?
C2 C3 H3 . . 120.6 ?
C4 C3 H3 . . 120.6 ?
C5 C4 C3 . . 121.3(2) ?
C5 C4 Br1 . . 119.64(18) ?
C3 C4 Br1 . . 119.10(19) ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 117.9(2) ?
C5 C6 C7 . . 119.1(2) ?
C1 C6 C7 . . 123.0(2) ?
N1 C7 C6 . . 121.5(2) ?
N1 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
O8 C8 N2 . . 121.5(2) ?
O8 C8 C9 . . 121.2(2) ?
N2 C8 C9 . . 117.29(18) ?
C14 C9 C10 . . 120.3(2) ?
C14 C9 C8 . . 117.02(19) ?
C10 C9 C8 . . 122.7(2) ?
C11 C10 C9 . . 118.6(2) ?
C11 C10 H10 . . 120.7 ?
C9 C10 H10 . . 120.7 ?
C10 C11 O11 . . 122.1(2) ?
C10 C11 C12 . . 121.8(2) ?
O11 C11 C12 . . 116.1(2) ?
C13 C12 C11 . . 118.9(2) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
O13 C13 C14 . . 122.5(2) ?
O13 C13 C12 . . 117.0(2) ?
C14 C13 C12 . . 120.4(2) ?
C13 C14 C9 . . 119.91(19) ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
H2A O2 H2B . . 105(3) ?
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 C4 . 1.899(2) ?
O1 C1 . 1.361(3) ?
O1 H1 . 0.812(18) ?
O8 C8 . 1.244(3) ?
O11 C11 . 1.381(3) ?
O11 H11 . 0.827(18) ?
O13 C13 . 1.361(3) ?
O13 H13 . 0.785(18) ?
N1 C7 . 1.279(3) ?
N1 N2 . 1.379(3) ?
N2 C8 . 1.341(3) ?
N2 H2N . 0.851(17) ?
C1 C2 . 1.383(4) ?
C1 C6 . 1.403(3) ?
C2 C3 . 1.375(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.389(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.372(3) ?
C5 C6 . 1.402(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.445(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.487(3) ?
C9 C14 . 1.389(3) ?
C9 C10 . 1.398(3) ?
C10 C11 . 1.375(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.388(3) ?
C12 C13 . 1.386(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.383(3) ?
C14 H14 . 0.9300 ?
O2 H2A . 0.807(18) ?
O2 H2B . 0.825(18) ?
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
_geom_hbond_publ_flag
O1 H1 N1 . 0.812(18) 1.95(2) 2.657(2) 145(3) yes
N2 H2N O2 . 0.851(17) 2.071(17) 2.913(3) 170(2) yes
O1 H1 O2 4_575 0.812(18) 2.52(3) 2.942(3) 114(3) no
O11 H11 O8 4_576 0.827(18) 1.937(19) 2.750(2) 168(3) yes
O13 H13 O1 2 0.785(18) 2.19(2) 2.959(2) 165(3) yes
O2 H2A O8 4_576 0.807(18) 1.976(19) 2.776(3) 171(4) yes
O2 H2B O11 2_546 0.825(18) 2.06(2) 2.861(3) 165(3) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656142
