#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/59/2215987.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_2215987
loop_
_publ_author_name
'Feng Zhi'
'Yi-Lin Yang'
_publ_section_title
;
 6-Chloro-N'-(2,4-dichlorobenzylidene)nicotinohydrazide
;
_journal_coeditor_code           HG2327
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4471
_journal_page_last               o4471
_journal_paper_doi               10.1107/S1600536807053184
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H8 Cl3 N3 O'
_chemical_formula_moiety         'C13 H8 Cl3 N3 O'
_chemical_formula_sum            'C13 H8 Cl3 N3 O'
_chemical_formula_weight         328.57
_chemical_name_systematic
;
6-Chloro-N'-(2,4-dichlorobenzylidene)nicotinohydrazide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.70(3)
_cell_angle_beta                 92.36(3)
_cell_angle_gamma                96.94(3)
_cell_formula_units_Z            2
_cell_length_a                   4.6670(9)
_cell_length_b                   12.202(2)
_cell_length_c                   12.935(3)
_cell_measurement_reflns_used    872
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.7
_cell_measurement_theta_min      2.5
_cell_volume                     698.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 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  0.0810
_diffrn_reflns_av_sigmaI/netI    0.1583
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5653
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.8696
_exptl_absorpt_correction_T_min  0.8434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.2038
_refine_ls_R_factor_gt           0.0857
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1898
_reflns_number_gt                1141
_reflns_number_total             2827
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2327.cif
_cod_data_source_block           I
_cod_original_cell_volume        698.1(2)
_cod_database_code               2215987
_cod_database_fobs_code          2215987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.3082(4) 0.10650(15) 0.49252(14) 0.0547(6) Uani d . 1
Cl Cl2 -0.3745(5) 0.04955(17) 0.13214(15) 0.0752(7) Uani d . 1
Cl Cl3 0.3929(5) 0.79974(18) 1.24132(15) 0.0810(8) Uani d . 1
O O1 -0.3459(9) 0.5648(4) 0.7653(3) 0.0499(13) Uani d . 1
N N1 -0.0622(11) 0.4126(4) 0.6298(4) 0.0408(14) Uani d . 1
N N2 0.0597(10) 0.4785(5) 0.7306(4) 0.0396(14) Uani d D 1
N N3 0.3450(11) 0.6333(5) 1.0617(4) 0.0488(15) Uani d . 1
C C1 -0.0062(13) 0.2716(5) 0.4667(5) 0.0347(15) Uani d . 1
C C2 0.0704(12) 0.1627(5) 0.4208(5) 0.0378(16) Uani d . 1
C C3 -0.0399(15) 0.0942(6) 0.3192(5) 0.055(2) Uani d . 1
H H3 0.0146 0.0214 0.2908 0.066 Uiso calc R 1
C C4 -0.2311(15) 0.1346(6) 0.2602(5) 0.0475(18) Uani d . 1
C C5 -0.3120(14) 0.2426(6) 0.3028(5) 0.0504(19) Uani d . 1
H H5 -0.4419 0.2696 0.2628 0.060 Uiso calc R 1
C C6 -0.2010(13) 0.3109(5) 0.4046(5) 0.0452(18) Uani d . 1
H H6 -0.2560 0.3837 0.4324 0.054 Uiso calc R 1
C C7 0.1035(14) 0.3441(6) 0.5761(5) 0.0439(18) Uani d . 1
H H7 0.2863 0.3405 0.6053 0.053 Uiso calc R 1
C C8 -0.1012(14) 0.5535(5) 0.7941(5) 0.0390(17) Uani d . 1
C C9 0.0401(13) 0.6207(6) 0.9038(5) 0.0382(16) Uani d . 1
C C10 -0.0519(14) 0.7242(6) 0.9563(5) 0.0504(19) Uani d . 1
H H10 -0.1877 0.7541 0.9215 0.061 Uiso calc R 1
C C11 0.0586(15) 0.7831(6) 1.0609(5) 0.056(2) Uani d . 1
H H11 0.0034 0.8537 1.0979 0.067 Uiso calc R 1
C C12 0.2527(15) 0.7327(6) 1.1074(5) 0.0494(19) Uani d . 1
C C13 0.2408(13) 0.5797(6) 0.9598(5) 0.0445(18) Uani d . 1
H H13 0.3066 0.5108 0.9243 0.053 Uiso calc R 1
H H2 0.251(4) 0.493(6) 0.750(5) 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'
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
C7 N1 N2 113.6(5)
C8 N2 N1 117.9(5)
C8 N2 H2 115(5)
N1 N2 H2 124(4)
C12 N3 C13 115.9(6)
C2 C1 C6 117.1(6)
C2 C1 C7 122.9(6)
C6 C1 C7 120.0(6)
C3 C2 C1 122.3(6)
C3 C2 Cl1 117.5(5)
C1 C2 Cl1 120.2(5)
C4 C3 C2 119.4(7)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 120.1(6)
C3 C4 Cl2 120.3(6)
C5 C4 Cl2 119.7(6)
C6 C5 C4 120.3(6)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 120.8(6)
C5 C6 H6 119.6
C1 C6 H6 119.6
N1 C7 C1 117.5(6)
N1 C7 H7 121.2
C1 C7 H7 121.2
O1 C8 N2 123.0(6)
O1 C8 C9 121.6(6)
N2 C8 C9 115.4(6)
C10 C9 C13 117.7(6)
C10 C9 C8 118.7(6)
C13 C9 C8 123.4(6)
C9 C10 C11 119.7(6)
C9 C10 H10 120.2
C11 C10 H10 120.2
C12 C11 C10 116.8(7)
C12 C11 H11 121.6
C10 C11 H11 121.6
N3 C12 C11 126.1(6)
N3 C12 Cl3 114.4(5)
C11 C12 Cl3 119.5(6)
N3 C13 C9 123.8(6)
N3 C13 H13 118.1
C9 C13 H13 118.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.740(6)
Cl2 C4 1.739(6)
Cl3 C12 1.750(7)
O1 C8 1.223(7)
N1 C7 1.283(7)
N1 N2 1.377(6)
N2 C8 1.364(7)
N2 H2 0.90(3)
N3 C12 1.319(8)
N3 C13 1.332(7)
C1 C2 1.388(8)
C1 C6 1.403(8)
C1 C7 1.469(8)
C2 C3 1.378(8)
C3 C4 1.373(8)
C3 H3 0.9300
C4 C5 1.380(9)
C5 C6 1.380(8)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.498(8)
C9 C10 1.379(8)
C9 C13 1.386(8)
C10 C11 1.380(8)
C10 H10 0.9300
C11 C12 1.365(9)
C11 H11 0.9300
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 O1 1_655 0.90(3) 1.95(3) 2.816(6) 160(6)
C5 H5 O1 2_466 0.93 2.46 3.291(6) 148
C13 H13 N3 2_667 0.93 2.57 3.379(6) 145
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21197041
