#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/15/2221509.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_2221509
loop_
_publ_author_name
'Ning, Jing-Heng'
'Xu, Xiao-Wu'
_publ_section_title
;
 3-Bromo-N'-(2-hydroxy-3,5-diiodobenzylidene)benzohydrazide
 monohydrate
;
_journal_coeditor_code           SJ2600
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o905
_journal_page_last               o906
_journal_paper_doi               10.1107/S1600536809010964
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H9 Br I2 N2 O2, H2 O'
_chemical_formula_moiety         'C14 H9 Br I2 N2 O2, H2 O'
_chemical_formula_sum            'C14 H11 Br I2 N2 O3'
_chemical_formula_weight         588.96
_chemical_name_systematic
;
3-Bromo-N'-(2-hydroxy-3,5-diiodobenzylidene)benzohydrazide 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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.628(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.181(3)
_cell_length_b                   7.611(2)
_cell_length_c                   15.516(3)
_cell_measurement_reflns_used    2004
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.6
_cell_volume                     1677.8(6)
_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 1000 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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13552
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.142
_exptl_absorpt_correction_T_max  0.293
_exptl_absorpt_correction_T_min  0.261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.686
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_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)+(0.0296P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                2651
_reflns_number_total             3656
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2600.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221509
_cod_database_fobs_code          2221509
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
I I1 0.32291(3) -0.01495(5) 0.20582(3) 0.04369(14) Uani d . 1 . .
I I2 0.14532(3) -0.04420(6) 0.49489(3) 0.04849(15) Uani d . 1 . .
Br Br1 1.04870(5) 0.64844(11) 0.62538(6) 0.0699(3) Uani d . 1 . .
O O1 0.4774(3) 0.1800(5) 0.3704(2) 0.0362(9) Uani d . 1 . .
H H1 0.5212 0.2190 0.4140 0.054 Uiso calc R 1 . .
O O2 0.6948(3) 0.4091(6) 0.4847(3) 0.0465(11) Uani d . 1 . .
O O3 0.4178(4) 0.0028(7) 0.7467(3) 0.0636(14) Uani d D 1 . .
N N1 0.5549(3) 0.3106(5) 0.5331(3) 0.0303(10) Uani d . 1 . .
N N2 0.6303(3) 0.3938(6) 0.5939(3) 0.0318(10) Uani d D 1 . .
C C1 0.4070(4) 0.1717(7) 0.4882(4) 0.0301(12) Uani d . 1 . .
C C2 0.4058(4) 0.1324(6) 0.3995(3) 0.0260(11) Uani d . 1 . .
C C3 0.3290(4) 0.0455(7) 0.3393(4) 0.0314(12) Uani d . 1 . .
C C4 0.2549(4) -0.0061(7) 0.3655(4) 0.0312(13) Uani d . 1 . .
H H4 0.2040 -0.0660 0.3244 0.037 Uiso calc R 1 . .
C C5 0.2572(4) 0.0324(7) 0.4540(4) 0.0333(13) Uani d . 1 . .
C C6 0.3317(4) 0.1209(7) 0.5138(4) 0.0325(13) Uani d . 1 . .
H H6 0.3323 0.1476 0.5724 0.039 Uiso calc R 1 . .
C C7 0.4852(4) 0.2632(7) 0.5544(4) 0.0323(13) Uani d . 1 . .
H H7 0.4844 0.2872 0.6129 0.039 Uiso calc R 1 . .
C C8 0.7013(4) 0.4386(7) 0.5641(4) 0.0304(12) Uani d . 1 . .
C C9 0.7872(4) 0.5200(6) 0.6326(4) 0.0301(12) Uani d . 1 . .
C C10 0.8620(4) 0.5467(7) 0.6036(4) 0.0389(14) Uani d . 1 . .
H H10 0.8576 0.5140 0.5444 0.047 Uiso calc R 1 . .
C C11 0.9424(4) 0.6211(8) 0.6616(4) 0.0429(15) Uani d . 1 . .
C C12 0.9500(4) 0.6747(9) 0.7478(5) 0.0530(17) Uani d . 1 . .
H H12 1.0052 0.7269 0.7863 0.064 Uiso calc R 1 . .
C C13 0.8755(4) 0.6511(8) 0.7772(4) 0.0489(16) Uani d . 1 . .
H H13 0.8802 0.6884 0.8357 0.059 Uiso calc R 1 . .
C C14 0.7934(5) 0.5721(7) 0.7204(4) 0.0422(15) Uani d . 1 . .
H H14 0.7433 0.5543 0.7407 0.051 Uiso calc R 1 . .
H H2 0.626(5) 0.411(9) 0.649(2) 0.080 Uiso d D 1 . .
H H3A 0.414(6) -0.082(4) 0.709(3) 0.080 Uiso d D 1 . .
H H3B 0.414(5) 0.097(3) 0.717(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'
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'
I I -0.4742 1.8119 '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 ?
H3A O3 H3B . . 107(3) ?
C7 N1 N2 . . 121.9(5) ?
N1 N2 C8 . . 117.2(4) ?
N1 N2 H2 . . 114(5) ?
C8 N2 H2 . . 129(5) ?
C6 C1 C2 . . 119.5(5) ?
C6 C1 C7 . . 118.9(5) ?
C2 C1 C7 . . 121.5(5) ?
O1 C2 C3 . . 119.0(4) ?
O1 C2 C1 . . 122.1(5) ?
C3 C2 C1 . . 118.8(5) ?
C4 C3 C2 . . 121.3(5) ?
C4 C3 I1 . . 118.2(4) ?
C2 C3 I1 . . 120.5(4) ?
C3 C4 C5 . . 119.4(5) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C6 C5 C4 . . 120.0(5) ?
C6 C5 I2 . . 120.0(4) ?
C4 C5 I2 . . 120.0(4) ?
C5 C6 C1 . . 120.9(5) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
N1 C7 C1 . . 120.3(5) ?
N1 C7 H7 . . 119.9 ?
C1 C7 H7 . . 119.9 ?
O2 C8 N2 . . 120.4(5) ?
O2 C8 C9 . . 122.2(5) ?
N2 C8 C9 . . 117.4(5) ?
C10 C9 C14 . . 120.0(5) ?
C10 C9 C8 . . 116.2(5) ?
C14 C9 C8 . . 123.7(5) ?
C11 C10 C9 . . 119.8(6) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C12 . . 121.4(6) ?
C10 C11 Br1 . . 120.5(5) ?
C12 C11 Br1 . . 118.1(5) ?
C11 C12 C13 . . 119.4(6) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.5(6) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C13 C14 C9 . . 118.8(6) ?
C13 C14 H14 . . 120.6 ?
C9 C14 H14 . . 120.6 ?
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
I1 C3 . 2.092(5) ?
I2 C5 . 2.094(6) ?
Br1 C11 . 1.898(6) ?
O1 C2 . 1.364(6) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.222(6) ?
O3 H3A . 0.86(4) ?
O3 H3B . 0.84(3) ?
N1 C7 . 1.267(6) ?
N1 N2 . 1.356(6) ?
N2 C8 . 1.357(7) ?
N2 H2 . 0.89(4) ?
C1 C6 . 1.390(7) ?
C1 C2 . 1.403(7) ?
C1 C7 . 1.445(7) ?
C2 C3 . 1.380(7) ?
C3 C4 . 1.379(7) ?
C4 C5 . 1.394(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.362(7) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.496(7) ?
C9 C10 . 1.377(8) ?
C9 C14 . 1.390(8) ?
C10 C11 . 1.359(8) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.363(9) ?
C12 C13 . 1.373(8) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.384(8) ?
C13 H13 . 0.9300 ?
C14 H14 . 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
O3 H3A O1 3_656 0.86(4) 2.50(6) 3.131(6) 132(6)
N2 H2 O3 2_656 0.89(4) 2.08(6) 2.934(6) 162(7)
O1 H1 N1 . 0.82 1.87 2.579(6) 144.1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655750
