#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221362.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_2221362
loop_
_publ_author_name
'Ren, Chun-yan'
_publ_section_title
(E)-6-Chloro-N'-(3,5-dichloro-2-hydroxybenzylidene)nicotinohydrazide
_journal_coeditor_code           HB2920
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o678
_journal_paper_doi               10.1107/S1600536809007272
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C13 H8 Cl3 N3 O2'
_chemical_formula_sum            'C13 H8 Cl3 N3 O2'
_chemical_formula_weight         344.57
_chemical_name_systematic
;
(E)-6-Chloro-N'-(3,5-dichloro-2-
hydroxybenzylidene)nicotinohydrazide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 97.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8920(10)
_cell_length_b                   18.014(4)
_cell_length_c                   16.112(3)
_cell_measurement_reflns_used    669
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.82
_cell_measurement_theta_min      2.59
_cell_volume                     1406.4(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART 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  0.0782
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7275
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1996)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0485
_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)+(0.0343P)²+0.2069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                1323
_reflns_number_total             2478
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2920.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221362
_cod_database_fobs_code          2221362
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 0.3842(2) 0.62724(6) 0.45177(7) 0.0534(3) Uani d . 1 . .
Cl Cl2 1.2166(3) 0.50424(7) 0.65897(7) 0.0651(4) Uani d . 1 . .
Cl Cl3 1.2331(3) 1.28010(7) 0.69130(8) 0.0698(4) Uani d . 1 . .
N N1 0.9665(7) 0.8466(2) 0.6071(2) 0.0471(9) Uani d . 1 . .
N N2 1.0608(7) 0.91708(18) 0.6266(2) 0.0474(9) Uani d . 1 . .
H H2 1.2318 0.9261 0.6437 0.057 Uiso calc R 1 . .
O O1 0.6119(6) 0.76626(15) 0.51866(18) 0.0542(8) Uani d . 1 . .
H H1 0.6800 0.8046 0.5397 0.081 Uiso calc R 1 . .
O O2 0.6214(6) 0.95721(16) 0.59872(19) 0.0619(9) Uani d . 1 . .
C C1 1.0059(8) 0.7165(2) 0.6081(2) 0.0408(10) Uani d . 1 . .
C C2 0.7633(8) 0.7076(2) 0.5502(2) 0.0399(10) Uani d . 1 . .
C C3 0.6750(8) 0.6374(2) 0.5262(2) 0.0411(11) Uani d . 1 . .
C C4 0.8115(8) 0.5751(2) 0.5595(3) 0.0455(11) Uani d . 1 . .
H H4 0.7479 0.5280 0.5428 0.055 Uiso calc R 1 . .
C C5 1.0456(9) 0.5834(2) 0.6182(3) 0.0461(11) Uani d . 1 . .
C C6 1.1444(9) 0.6532(2) 0.6417(3) 0.0450(11) Uani d . 1 . .
H H6 1.3036 0.6581 0.6801 0.054 Uiso calc R 1 . .
C C7 1.1106(9) 0.7906(3) 0.6314(2) 0.0452(11) Uani d . 1 . .
H H7 1.2817 0.7964 0.6639 0.054 Uiso calc R 1 . .
C C8 0.8673(9) 0.9716(2) 0.6171(3) 0.0450(11) Uani d . 1 . .
C C9 0.9672(8) 1.0483(2) 0.6324(3) 0.0410(10) Uani d . 1 . .
C C10 0.8110(9) 1.1062(2) 0.5936(3) 0.0506(12) Uani d . 1 . .
H H10 0.6519 1.0962 0.5566 0.061 Uiso calc R 1 . .
C C11 0.8935(9) 1.1786(3) 0.6102(3) 0.0543(12) Uani d . 1 . .
H H11 0.7949 1.2183 0.5842 0.065 Uiso calc R 1 . .
C C12 1.1270(9) 1.1895(2) 0.6666(3) 0.0477(12) Uani d . 1 . .
N N3 1.2807(7) 1.1365(2) 0.7059(2) 0.0502(10) Uani d . 1 . .
C C13 1.1988(9) 1.0670(2) 0.6874(3) 0.0493(11) Uani d . 1 . .
H H13 1.3051 1.0285 0.7133 0.059 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'
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 . . 120.9(4) ?
C8 N2 N1 . . 115.9(4) ?
C8 N2 H2 . . 122.1 ?
N1 N2 H2 . . 122.1 ?
C2 O1 H1 . . 109.5 ?
C6 C1 C2 . . 118.8(4) ?
C6 C1 C7 . . 120.8(4) ?
C2 C1 C7 . . 120.4(4) ?
O1 C2 C3 . . 118.6(4) ?
O1 C2 C1 . . 121.8(4) ?
C3 C2 C1 . . 119.5(4) ?
C2 C3 C4 . . 121.5(4) ?
C2 C3 Cl1 . . 119.1(3) ?
C4 C3 Cl1 . . 119.4(3) ?
C3 C4 C5 . . 119.3(4) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C6 C5 C4 . . 120.6(4) ?
C6 C5 Cl2 . . 120.8(4) ?
C4 C5 Cl2 . . 118.6(3) ?
C5 C6 C1 . . 120.3(4) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
N1 C7 C1 . . 119.3(4) ?
N1 C7 H7 . . 120.3 ?
C1 C7 H7 . . 120.3 ?
O2 C8 N2 . . 121.3(4) ?
O2 C8 C9 . . 122.0(4) ?
N2 C8 C9 . . 116.7(4) ?
C13 C9 C10 . . 117.2(4) ?
C13 C9 C8 . . 124.0(4) ?
C10 C9 C8 . . 118.6(4) ?
C11 C10 C9 . . 119.6(4) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 117.3(4) ?
C12 C11 H11 . . 121.4 ?
C10 C11 H11 . . 121.4 ?
N3 C12 C11 . . 125.5(4) ?
N3 C12 Cl3 . . 115.8(3) ?
C11 C12 Cl3 . . 118.7(4) ?
C12 N3 C13 . . 115.9(4) ?
N3 C13 C9 . . 124.5(4) ?
N3 C13 H13 . . 117.7 ?
C9 C13 H13 . . 117.7 ?
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 C3 . 1.739(4) ?
Cl2 C5 . 1.736(4) ?
Cl3 C12 . 1.742(4) ?
N1 C7 . 1.263(5) ?
N1 N2 . 1.372(4) ?
N2 C8 . 1.358(5) ?
N2 H2 . 0.8600 ?
O1 C2 . 1.349(4) ?
O1 H1 . 0.8200 ?
O2 C8 . 1.227(5) ?
C1 C6 . 1.396(5) ?
C1 C2 . 1.414(5) ?
C1 C7 . 1.460(5) ?
C2 C3 . 1.375(5) ?
C3 C4 . 1.376(5) ?
C4 C5 . 1.389(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.474(5) ?
C9 C13 . 1.380(5) ?
C9 C10 . 1.391(5) ?
C10 C11 . 1.380(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.373(6) ?
C11 H11 . 0.9300 ?
C12 N3 . 1.321(5) ?
N3 C13 . 1.337(5) ?
C13 H13 . 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 O2 1_655 0.86 2.20 2.930(4) 142
O1 H1 N1 . 0.82 1.82 2.540(4) 147
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741864
