#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/02/2220204.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_2220204
loop_
_publ_author_name
'Yehye, Wagee A.'
'Ariffin, Azhar'
'Rahman, Noorsaadah A.'
'Ng, Seik Weng'
_publ_section_title
;
 N'-(3-Bromo-5-chloro-2-hydroxybenzylidine)-2-hydroxybenzohydrazide
;
_journal_coeditor_code           HB2857
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2438
_journal_paper_doi               10.1107/S1600536808038634
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H10 Br Cl N2 O3'
_chemical_formula_moiety         'C14 H10 Br Cl N2 O3'
_chemical_formula_sum            'C14 H10 Br Cl N2 O3'
_chemical_formula_weight         369.60
_chemical_name_systematic
;
N'-(3-Bromo-5-chloro-2-hydroxybenzylidine)-2-hydroxybenzohydrazide
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.4610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8387(3)
_cell_length_b                   6.93190(10)
_cell_length_c                   12.9951(3)
_cell_measurement_reflns_used    3691
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      3.2
_cell_volume                     1368.28(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  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12350
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.210
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.414
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0288
_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)+(0.0353P)²+1.3959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                2545
_reflns_number_total             3136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2857.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220204
_cod_database_fobs_code          2220204
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
Br Br1 0.145097(18) 0.43521(4) 0.04463(2) 0.02196(9) Uani d . 1
Cl Cl1 -0.04591(4) 0.45367(9) 0.33930(5) 0.01932(14) Uani d . 1
O O1 0.48671(11) 0.8436(3) 0.72174(14) 0.0186(4) Uani d D 1
H H1O 0.495(2) 0.837(5) 0.7879(9) 0.033(9) Uiso d D 1
O O2 0.52114(12) 0.6952(3) 0.42779(14) 0.0224(4) Uani d . 1
O O3 0.28679(12) 0.5844(3) 0.23371(14) 0.0184(4) Uani d D 1
H H3O 0.3254(15) 0.616(4) 0.2897(15) 0.027(9) Uiso d D 1
N N1 0.42237(13) 0.7471(3) 0.52022(16) 0.0142(4) Uani d D 1
H H1N 0.4157(17) 0.778(4) 0.5825(12) 0.015(7) Uiso d D 1
N N2 0.35545(13) 0.6804(3) 0.43620(16) 0.0154(4) Uani d . 1
C C1 0.56768(15) 0.8577(4) 0.70555(19) 0.0140(5) Uani d . 1
C C2 0.64075(16) 0.9151(4) 0.7881(2) 0.0163(5) Uani d . 1
H H2 0.6343 0.9445 0.8569 0.020 Uiso calc R 1
C C3 0.72242(16) 0.9295(4) 0.7702(2) 0.0171(5) Uani d . 1
H H3 0.7720 0.9670 0.8271 0.021 Uiso calc R 1
C C4 0.73279(16) 0.8897(4) 0.6701(2) 0.0174(5) Uani d . 1
H H4 0.7890 0.9010 0.6581 0.021 Uiso calc R 1
C C5 0.66035(16) 0.8333(4) 0.5875(2) 0.0158(5) Uani d . 1
H H5 0.6674 0.8061 0.5187 0.019 Uiso calc R 1
C C6 0.57684(15) 0.8157(3) 0.60395(19) 0.0131(5) Uani d . 1
C C7 0.50521(16) 0.7480(3) 0.51062(19) 0.0149(5) Uani d . 1
C C8 0.27901(16) 0.6691(4) 0.4507(2) 0.0154(5) Uani d . 1
H H8 0.2706 0.7070 0.5174 0.018 Uiso calc R 1
C C9 0.20470(16) 0.5978(3) 0.3648(2) 0.0155(5) Uani d . 1
C C10 0.21190(16) 0.5580(3) 0.2611(2) 0.0153(5) Uani d . 1
C C11 0.13777(17) 0.4882(4) 0.1845(2) 0.0162(5) Uani d . 1
C C12 0.05895(16) 0.4549(3) 0.2073(2) 0.0169(5) Uani d . 1
H H12 0.0095 0.4062 0.1538 0.020 Uiso calc R 1
C C13 0.05363(16) 0.4941(4) 0.3096(2) 0.0163(5) Uani d . 1
C C14 0.12487(17) 0.5652(3) 0.3880(2) 0.0171(5) Uani d . 1
H H14 0.1197 0.5921 0.4577 0.020 Uiso calc R 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
C1 O1 H1O 106(2)
C10 O3 H3O 107(2)
C7 N1 N2 118.7(2)
C7 N1 H1N 117.4(18)
N2 N1 H1N 123.5(18)
C8 N2 N1 117.0(2)
O1 C1 C2 121.0(2)
O1 C1 C6 119.0(2)
C2 C1 C6 120.0(2)
C3 C2 C1 120.2(2)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 120.7(2)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C5 119.4(2)
C3 C4 H4 120.3
C5 C4 H4 120.3
C4 C5 C6 121.0(2)
C4 C5 H5 119.5
C6 C5 H5 119.5
C1 C6 C5 118.7(2)
C1 C6 C7 125.3(2)
C5 C6 C7 116.0(2)
O2 C7 N1 121.6(2)
O2 C7 C6 120.8(2)
N1 C7 C6 117.6(2)
N2 C8 C9 120.0(2)
N2 C8 H8 120.0
C9 C8 H8 120.0
C14 C9 C10 119.8(2)
C14 C9 C8 118.2(2)
C10 C9 C8 122.0(2)
O3 C10 C11 119.1(2)
O3 C10 C9 122.8(2)
C11 C10 C9 118.0(2)
C12 C11 C10 122.3(2)
C12 C11 Br1 118.63(19)
C10 C11 Br1 119.05(19)
C11 C12 C13 118.6(2)
C11 C12 H12 120.7
C13 C12 H12 120.7
C14 C13 C12 121.3(2)
C14 C13 Cl1 119.6(2)
C12 C13 Cl1 119.01(19)
C13 C14 C9 119.9(2)
C13 C14 H14 120.0
C9 C14 H14 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.890(3)
Cl1 C13 1.749(3)
O1 C1 1.361(3)
O1 H1O 0.833(10)
O2 C7 1.229(3)
O3 C10 1.344(3)
O3 H3O 0.836(10)
N1 C7 1.353(3)
N1 N2 1.369(3)
N1 H1N 0.872(10)
N2 C8 1.279(3)
C1 C2 1.395(3)
C1 C6 1.399(3)
C2 C3 1.382(4)
C2 H2 0.9500
C3 C4 1.384(4)
C3 H3 0.9500
C4 C5 1.387(4)
C4 H4 0.9500
C5 C6 1.404(3)
C5 H5 0.9500
C6 C7 1.483(3)
C8 C9 1.459(3)
C8 H8 0.9500
C9 C14 1.399(4)
C9 C10 1.412(4)
C10 C11 1.393(3)
C11 C12 1.382(4)
C12 C13 1.383(4)
C12 H12 0.9500
C13 C14 1.379(4)
C14 H14 0.9500
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 H1o O2 4_576 0.830(10) 1.760(10) 2.591(2) 175(3) y
O3 H3o N2 . 0.840(10) 1.88(2) 2.632(3) 149(3) y
N1 H1n O1 . 0.870(10) 1.90(2) 2.614(3) 139(2) y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 N1 N2 C8 175.3(2)
O1 C1 C2 C3 -179.7(2)
C6 C1 C2 C3 -0.5(4)
C1 C2 C3 C4 0.8(4)
C2 C3 C4 C5 -0.6(4)
C3 C4 C5 C6 -0.1(4)
O1 C1 C6 C5 179.1(2)
C2 C1 C6 C5 -0.2(4)
O1 C1 C6 C7 -2.6(4)
C2 C1 C6 C7 178.1(2)
C4 C5 C6 C1 0.4(4)
C4 C5 C6 C7 -178.0(2)
N2 N1 C7 O2 1.8(4)
N2 N1 C7 C6 -178.3(2)
C1 C6 C7 O2 -172.2(2)
C5 C6 C7 O2 6.1(3)
C1 C6 C7 N1 7.9(4)
C5 C6 C7 N1 -173.8(2)
N1 N2 C8 C9 -179.6(2)
N2 C8 C9 C14 172.3(2)
N2 C8 C9 C10 -6.4(4)
C14 C9 C10 O3 -179.4(2)
C8 C9 C10 O3 -0.7(4)
C14 C9 C10 C11 0.5(4)
C8 C9 C10 C11 179.2(2)
O3 C10 C11 C12 179.1(2)
C9 C10 C11 C12 -0.9(4)
O3 C10 C11 Br1 -0.5(3)
C9 C10 C11 Br1 179.55(18)
C10 C11 C12 C13 0.6(4)
Br1 C11 C12 C13 -179.88(18)
C11 C12 C13 C14 0.1(4)
C11 C12 C13 Cl1 179.70(19)
C12 C13 C14 C9 -0.5(4)
Cl1 C13 C14 C9 179.98(18)
C10 C9 C14 C13 0.1(4)
C8 C9 C14 C13 -178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21824329
