#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/35/2223508.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_2223508
loop_
_publ_author_name
'Cao, Guo-Biao'
_publ_section_title
;
 (E)-4-Chloro-N'-(2-chlorobenzylidene)benzohydrazide
;
_journal_coeditor_code           OM2272
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2384
_journal_paper_doi               10.1107/S1600536809035739
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 Cl2 N2 O'
_chemical_formula_moiety         'C14 H10 Cl2 N2 O'
_chemical_formula_sum            'C14 H10 Cl2 N2 O'
_chemical_formula_weight         293.14
_chemical_name_systematic
;
(E)-4-Chloro-N'-(2-chlorobenzylidene)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                 96.165(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9140(4)
_cell_length_b                   13.3253(4)
_cell_length_c                   9.1283(3)
_cell_measurement_reflns_used    2259
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.4
_cell_volume                     1319.87(8)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1K'
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7970
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.9180
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0374
_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)+(0.0443P)²+0.3326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2099
_reflns_number_total             2863
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2272.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223508
_cod_database_fobs_code          2223508
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 0.23751(6) 0.62666(4) 1.13145(6) 0.0669(2) Uani d . 1 . .
Cl Cl2 0.45481(6) -0.17289(4) 1.34138(7) 0.0725(2) Uani d . 1 . .
N N1 0.19376(14) 0.33512(10) 0.93524(16) 0.0400(4) Uani d . 1 . .
N N2 0.23897(15) 0.25647(11) 1.02386(16) 0.0394(4) Uani d D 1 . .
O O1 0.27146(14) 0.16448(10) 0.82336(13) 0.0503(4) Uani d . 1 . .
C C1 0.13324(16) 0.50527(13) 0.9130(2) 0.0404(4) Uani d . 1 . .
C C2 0.15065(18) 0.60340(14) 0.9639(2) 0.0442(4) Uani d . 1 . .
C C3 0.1036(2) 0.68464(15) 0.8830(2) 0.0543(5) Uani d . 1 . .
H H3 0.1166 0.7494 0.9193 0.065 Uiso calc R 1 . .
C C4 0.0371(2) 0.66901(17) 0.7480(3) 0.0600(6) Uani d . 1 . .
H H4 0.0048 0.7234 0.6929 0.072 Uiso calc R 1 . .
C C5 0.0185(2) 0.57327(17) 0.6945(2) 0.0586(6) Uani d . 1 . .
H H5 -0.0263 0.5630 0.6032 0.070 Uiso calc R 1 . .
C C6 0.06591(18) 0.49246(15) 0.7758(2) 0.0487(5) Uani d . 1 . .
H H6 0.0527 0.4280 0.7383 0.058 Uiso calc R 1 . .
C C7 0.18227(18) 0.41876(13) 0.9994(2) 0.0423(4) Uani d . 1 . .
H H7 0.2048 0.4250 1.1002 0.051 Uiso calc R 1 . .
C C8 0.27714(17) 0.17307(13) 0.95759(19) 0.0376(4) Uani d . 1 . .
C C9 0.32468(17) 0.08966(12) 1.05677(18) 0.0359(4) Uani d . 1 . .
C C10 0.37559(18) 0.10432(13) 1.20078(19) 0.0411(4) Uani d . 1 . .
H H10 0.3812 0.1688 1.2399 0.049 Uiso calc R 1 . .
C C11 0.41803(19) 0.02376(14) 1.2864(2) 0.0477(5) Uani d . 1 . .
H H11 0.4537 0.0340 1.3824 0.057 Uiso calc R 1 . .
C C12 0.40759(18) -0.07139(14) 1.2298(2) 0.0456(5) Uani d . 1 . .
C C13 0.3595(2) -0.08810(14) 1.0865(2) 0.0570(6) Uani d . 1 . .
H H13 0.3541 -0.1529 1.0484 0.068 Uiso calc R 1 . .
C C14 0.3195(2) -0.00707(14) 1.0001(2) 0.0521(5) Uani d . 1 . .
H H14 0.2885 -0.0174 0.9023 0.063 Uiso calc R 1 . .
H H2 0.2458(17) 0.2649(15) 1.1210(11) 0.048(6) 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 . . 116.21(14) ?
C8 N2 N1 . . 117.98(14) ?
C8 N2 H2 . . 123.6(13) ?
N1 N2 H2 . . 118.3(13) ?
C6 C1 C2 . . 117.03(17) ?
C6 C1 C7 . . 120.97(17) ?
C2 C1 C7 . . 122.00(17) ?
C3 C2 C1 . . 121.92(19) ?
C3 C2 Cl1 . . 117.90(16) ?
C1 C2 Cl1 . . 120.15(14) ?
C4 C3 C2 . . 119.4(2) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C5 C4 C3 . . 120.14(19) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.2(2) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 121.34(19) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
N1 C7 C1 . . 119.33(16) ?
N1 C7 H7 . . 120.3 ?
C1 C7 H7 . . 120.3 ?
O1 C8 N2 . . 122.62(16) ?
O1 C8 C9 . . 120.95(16) ?
N2 C8 C9 . . 116.41(14) ?
C10 C9 C14 . . 118.77(16) ?
C10 C9 C8 . . 123.30(15) ?
C14 C9 C8 . . 117.92(15) ?
C11 C10 C9 . . 120.28(17) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 119.86(17) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 121.14(17) ?
C11 C12 Cl2 . . 119.47(15) ?
C13 C12 Cl2 . . 119.39(15) ?
C12 C13 C14 . . 118.83(18) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C13 C14 C9 . . 121.04(18) ?
C13 C14 H14 . . 119.5 ?
C9 C14 H14 . . 119.5 ?
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
Cl1 C2 . 1.739(2) ?
Cl2 C12 . 1.7379(19) ?
N1 C7 . 1.272(2) ?
N1 N2 . 1.3822(19) ?
N2 C8 . 1.352(2) ?
N2 H2 . 0.889(9) ?
O1 C8 . 1.225(2) ?
C1 C6 . 1.393(3) ?
C1 C2 . 1.394(3) ?
C1 C7 . 1.465(2) ?
C2 C3 . 1.378(3) ?
C3 C4 . 1.377(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.491(2) ?
C9 C10 . 1.385(2) ?
C9 C14 . 1.388(2) ?
C10 C11 . 1.378(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.369(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.374(3) ?
C13 C14 . 1.380(3) ?
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_566 0.889(9) 2.065(11) 2.9157(18) 159.8(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5279529
