#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228737.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_2228737
loop_
_publ_author_name
'Lei, Yan'
_publ_section_title
;
 3-Chloro-N'-(2,4-dichlorobenzylidene)benzohydrazide
;
_journal_coeditor_code           HB5766
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o162
_journal_paper_doi               10.1107/S1600536810051913
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H9 Cl3 N2 O'
_chemical_formula_moiety         'C14 H9 Cl3 N2 O'
_chemical_formula_sum            'C14 H9 Cl3 N2 O'
_chemical_formula_weight         327.58
_chemical_name_systematic
;
3-Chloro-N'-(2,4-dichlorobenzylidene)benzohydrazide
;
_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                 97.582(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.372(3)
_cell_length_b                   14.071(2)
_cell_length_c                   8.332(2)
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.3
_cell_volume                     1437.8(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART 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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7125
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.8479
_exptl_absorpt_correction_T_min  0.8330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut from needle'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.344
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0544
_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)+(0.0422P)²+0.3462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                1776
_reflns_number_total             3081
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5766.cif
_cod_data_source_block           I
_cod_original_cell_volume        1437.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228737
_cod_database_fobs_code          2228737
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
Cl Cl1 0.50321(9) 1.17766(6) 0.13090(13) 0.0852(4) Uani d . 1 . .
Cl Cl2 0.27379(8) 1.10398(6) 0.61537(13) 0.0791(3) Uani d . 1 . .
Cl Cl3 0.12211(9) 0.31908(6) 0.63795(16) 0.1013(5) Uani d . 1 . .
N N1 0.27659(18) 0.81292(16) 0.4682(3) 0.0403(6) Uani d . 1 . .
N N2 0.22918(19) 0.74940(16) 0.5631(3) 0.0408(6) Uani d D 1 . .
O O1 0.20262(17) 0.64606(14) 0.3554(2) 0.0544(6) Uani d . 1 . .
C C1 0.3473(2) 0.96532(19) 0.4329(3) 0.0384(7) Uani d . 1 . .
C C2 0.3406(2) 1.0619(2) 0.4604(4) 0.0456(8) Uani d . 1 . .
C C3 0.3859(2) 1.1283(2) 0.3661(4) 0.0528(8) Uani d . 1 . .
H H3 0.3788 1.1930 0.3845 0.063 Uiso calc R 1 . .
C C4 0.4413(2) 1.0962(2) 0.2456(4) 0.0503(8) Uani d . 1 . .
C C5 0.4516(2) 1.0012(2) 0.2160(4) 0.0503(8) Uani d . 1 . .
H H5 0.4903 0.9805 0.1342 0.060 Uiso calc R 1 . .
C C6 0.4041(2) 0.9370(2) 0.3086(3) 0.0435(7) Uani d . 1 . .
H H6 0.4102 0.8724 0.2874 0.052 Uiso calc R 1 . .
C C7 0.2964(2) 0.8950(2) 0.5281(4) 0.0418(7) Uani d . 1 . .
H H7 0.2790 0.9101 0.6302 0.050 Uiso calc R 1 . .
C C8 0.1933(2) 0.66637(19) 0.4955(4) 0.0396(7) Uani d . 1 . .
C C9 0.1403(2) 0.59954(19) 0.5991(3) 0.0361(6) Uani d . 1 . .
C C10 0.1539(2) 0.5032(2) 0.5755(4) 0.0475(8) Uani d . 1 . .
H H10 0.1974 0.4820 0.4999 0.057 Uiso calc R 1 . .
C C11 0.1030(3) 0.4393(2) 0.6640(4) 0.0582(9) Uani d . 1 . .
C C12 0.0359(3) 0.4696(3) 0.7725(4) 0.0723(11) Uani d . 1 . .
H H12 0.0004 0.4258 0.8307 0.087 Uiso calc R 1 . .
C C13 0.0219(3) 0.5651(3) 0.7939(4) 0.0663(10) Uani d . 1 . .
H H13 -0.0235 0.5860 0.8671 0.080 Uiso calc R 1 . .
C C14 0.0743(2) 0.6307(2) 0.7086(3) 0.0490(8) Uani d . 1 . .
H H14 0.0650 0.6954 0.7250 0.059 Uiso calc R 1 . .
H H2 0.227(2) 0.763(2) 0.6680(15) 0.059 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'
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 . . 116.1(2) ?
C8 N2 N1 . . 117.7(2) ?
C8 N2 H2 . . 122.6(19) ?
N1 N2 H2 . . 119.5(19) ?
C2 C1 C6 . . 117.1(3) ?
C2 C1 C7 . . 122.4(3) ?
C6 C1 C7 . . 120.5(3) ?
C1 C2 C3 . . 122.1(3) ?
C1 C2 Cl2 . . 120.4(2) ?
C3 C2 Cl2 . . 117.5(2) ?
C4 C3 C2 . . 118.3(3) ?
C4 C3 H3 . . 120.8 ?
C2 C3 H3 . . 120.8 ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 Cl1 . . 119.2(2) ?
C5 C4 Cl1 . . 119.2(3) ?
C4 C5 C6 . . 119.1(3) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C5 C6 C1 . . 121.9(3) ?
C5 C6 H6 . . 119.0 ?
C1 C6 H6 . . 119.0 ?
N1 C7 C1 . . 118.5(3) ?
N1 C7 H7 . . 120.7 ?
C1 C7 H7 . . 120.7 ?
O1 C8 N2 . . 122.4(3) ?
O1 C8 C9 . . 120.8(3) ?
N2 C8 C9 . . 116.8(3) ?
C14 C9 C10 . . 120.1(3) ?
C14 C9 C8 . . 122.0(3) ?
C10 C9 C8 . . 117.8(3) ?
C11 C10 C9 . . 119.6(3) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C12 . . 120.8(3) ?
C10 C11 Cl3 . . 119.7(3) ?
C12 C11 Cl3 . . 119.5(3) ?
C13 C12 C11 . . 119.2(3) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C14 . . 120.9(3) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C9 C14 C13 . . 119.3(3) ?
C9 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
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
Cl1 C4 . 1.733(3) ?
Cl2 C2 . 1.728(3) ?
Cl3 C11 . 1.726(3) ?
N1 C7 . 1.269(3) ?
N1 N2 . 1.375(3) ?
N2 C8 . 1.347(3) ?
N2 H2 . 0.896(10) ?
O1 C8 . 1.222(3) ?
C1 C2 . 1.382(4) ?
C1 C6 . 1.384(4) ?
C1 C7 . 1.462(4) ?
C2 C3 . 1.386(4) ?
C3 C4 . 1.365(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(4) ?
C5 C6 . 1.370(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.487(4) ?
C9 C14 . 1.374(4) ?
C9 C10 . 1.383(4) ?
C10 C11 . 1.368(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.373(5) ?
C12 C13 . 1.371(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.377(4) ?
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
N2 H2 O1 4_576 0.896(10) 2.076(16) 2.900(3) 152(3)
C7 H7 O1 4_576 0.93 2.35 3.155(3) 145
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5281072
