#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/98/2219845.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_2219845
loop_
_publ_author_name
'Shi, Zhi-Qiang'
'Ji, Ning-Ning'
'Li, Xiao-Yan'
_publ_section_title
;
 1-(2-Chlorobenzylidene)-2-(2,4-dinitrophenyl)hydrazine
;
_journal_coeditor_code           FJ2153
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2135
_journal_paper_doi               10.1107/S1600536808033357
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H9 Cl N4 O4'
_chemical_formula_moiety         'C13 H9 Cl N4 O4'
_chemical_formula_sum            'C13 H9 Cl N4 O4'
_chemical_formula_weight         320.69
_chemical_name_systematic
;
1-(2-Chlorobenzylidene)-2-(2,4-dinitrophenyl)hydrazine
;
_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
_cell_angle_alpha                95.691(2)
_cell_angle_beta                 93.030(2)
_cell_angle_gamma                99.728(3)
_cell_formula_units_Z            4
_cell_length_a                   7.2286(7)
_cell_length_b                   7.6596(8)
_cell_length_c                   25.145(2)
_cell_measurement_reflns_used    1793
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.9275
_cell_measurement_theta_min      2.7325
_cell_volume                     1362.0(2)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7216
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0470
_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)+(0.0511P)²+0.2987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                3273
_reflns_number_total             4776
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2153.cif
_cod_data_source_block           I
_cod_database_code               2219845
_cod_database_fobs_code          2219845
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 0.32732(10) 0.39535(11) 0.21587(3) 0.0647(2) Uani d . 1
Cl Cl2 0.43812(11) 0.46461(12) 0.65151(3) 0.0739(3) Uani d . 1
O O1 1.1413(3) 0.8066(3) 0.24502(8) 0.0769(6) Uani d . 1
O O2 1.4364(3) 0.8957(4) 0.23973(8) 0.0901(8) Uani d . 1
O O3 1.6810(3) 1.1413(4) 0.08840(11) 0.1047(9) Uani d . 1
O O4 1.4958(3) 1.1774(3) 0.02231(9) 0.0754(6) Uani d . 1
O O5 -0.0518(4) -0.1695(3) 0.37193(10) 0.0957(8) Uani d . 1
O O6 0.0550(3) -0.0357(3) 0.44708(4) 0.0817(7) Uani d D 1
O O7 -0.1612(4) 0.1254(4) 0.22106(9) 0.0899(8) Uani d . 1
O O8 -0.1463(3) 0.4102(3) 0.23032(8) 0.0804(7) Uani d . 1
N N1 0.7500(3) 0.6855(3) 0.12714(8) 0.0490(5) Uani d . 1
N N2 0.9138(3) 0.7485(3) 0.15793(8) 0.0506(6) Uani d . 1
H H2 0.9218 0.7309 0.1912 0.061 Uiso calc R 1
N N3 1.2749(4) 0.8647(3) 0.21971(9) 0.0586(6) Uani d . 1
N N4 1.5265(4) 1.1204(3) 0.06490(11) 0.0626(7) Uani d . 1
N N5 0.2250(3) 0.4769(3) 0.48803(9) 0.0544(6) Uani d . 1
N N6 0.1464(3) 0.3138(3) 0.46212(8) 0.0555(6) Uani d . 1
H H6 0.1359 0.2206 0.4790 0.067 Uiso calc R 1
N N7 0.0038(3) -0.0334(3) 0.40054(10) 0.0584(6) Uani d . 1
N N8 -0.1249(3) 0.2712(4) 0.24773(9) 0.0613(6) Uani d . 1
C C1 0.2909(3) 0.4329(3) 0.14910(10) 0.0440(6) Uani d . 1
C C2 0.4356(3) 0.5294(3) 0.12368(10) 0.0428(6) Uani d . 1
C C3 0.3991(4) 0.5523(4) 0.07027(10) 0.0508(7) Uani d . 1
H H3 0.4928 0.6154 0.0522 0.061 Uiso calc R 1
C C4 0.2273(4) 0.4835(4) 0.04363(11) 0.0565(7) Uani d . 1
H H4 0.2058 0.5001 0.0078 0.068 Uiso calc R 1
C C5 0.0867(4) 0.3899(4) 0.06992(11) 0.0558(7) Uani d . 1
H H5 -0.0295 0.3438 0.0518 0.067 Uiso calc R 1
C C6 0.1179(4) 0.3646(3) 0.12285(11) 0.0506(7) Uani d . 1
H H6A 0.0232 0.3020 0.1407 0.061 Uiso calc R 1
C C7 0.6178(3) 0.6038(3) 0.15160(10) 0.0470(6) Uani d . 1
H H7 0.6378 0.5915 0.1878 0.056 Uiso calc R 1
C C8 1.0634(3) 0.8386(3) 0.13611(10) 0.0436(6) Uani d . 1
C C9 1.2406(3) 0.8962(3) 0.16462(10) 0.0450(6) Uani d . 1
C C10 1.3931(3) 0.9855(3) 0.14090(10) 0.0466(6) Uani d . 1
H H10 1.5096 1.0204 0.1599 0.056 Uiso calc R 1
C C11 1.3680(4) 1.0207(3) 0.08927(10) 0.0479(6) Uani d . 1
C C12 1.1976(4) 0.9667(4) 0.05948(11) 0.0522(7) Uani d . 1
H H12 1.1849 0.9913 0.0241 0.063 Uiso calc R 1
C C13 1.0483(4) 0.8770(3) 0.08255(10) 0.0501(7) Uani d . 1
H H13 0.9341 0.8404 0.0625 0.060 Uiso calc R 1
C C14 0.4405(4) 0.6574(4) 0.62064(11) 0.0555(7) Uani d . 1
C C15 0.3642(4) 0.6497(4) 0.56796(10) 0.0517(7) Uani d . 1
C C16 0.3711(4) 0.8103(4) 0.54624(12) 0.0626(8) Uani d . 1
H H16 0.3214 0.8099 0.5113 0.075 Uiso calc R 1
C C17 0.4496(4) 0.9698(5) 0.57508(13) 0.0700(9) Uani d . 1
H H17 0.4537 1.0755 0.5595 0.084 Uiso calc R 1
C C18 0.5230(4) 0.9733(5) 0.62741(13) 0.0713(9) Uani d . 1
H H18 0.5753 1.0813 0.6471 0.086 Uiso calc R 1
C C19 0.5181(4) 0.8170(5) 0.65008(12) 0.0664(8) Uani d . 1
H H19 0.5669 0.8187 0.6851 0.080 Uiso calc R 1
C C20 0.2786(4) 0.4815(4) 0.53736(10) 0.0548(7) Uani d . 1
H H20 0.2629 0.3771 0.5539 0.066 Uiso calc R 1
C C21 0.0852(3) 0.2998(4) 0.40979(10) 0.0451(6) Uani d . 1
C C22 0.0134(3) 0.1353(3) 0.37897(10) 0.0461(6) Uani d . 1
C C23 -0.0515(3) 0.1268(4) 0.32600(10) 0.0482(6) Uani d . 1
H H23 -0.0975 0.0172 0.3064 0.058 Uiso calc R 1
C C24 -0.0474(3) 0.2805(4) 0.30277(9) 0.0462(6) Uani d . 1
C C25 0.0247(4) 0.4448(4) 0.33107(10) 0.0512(7) Uani d . 1
H H25 0.0282 0.5484 0.3145 0.061 Uiso calc R 1
C C26 0.0902(4) 0.4542(4) 0.38328(10) 0.0513(7) Uani d . 1
H H26 0.1394 0.5649 0.4018 0.062 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
C7 N1 N2 . . 115.0(2)
C8 N2 N1 . . 120.0(2)
C8 N2 H2 . . 120.0
N1 N2 H2 . . 120.0
O2 N3 O1 . 1 121.8(2)
O2 N3 O1 . . 121.8(2)
O2 N3 C9 . . 118.9(2)
O1 N3 C9 1 . 119.2(2)
O1 N3 C9 . . 119.2(2)
O3 N4 O4 . . 123.9(3)
O3 N4 C11 . . 117.9(3)
O4 N4 C11 . . 118.2(3)
C20 N5 N6 . . 116.6(2)
C21 N6 N5 . . 119.6(2)
C21 N6 H6 . . 120.2
N5 N6 H6 . . 120.2
O5 N7 O6 . 1 120.9(2)
O5 N7 O6 . . 120.9(2)
O5 N7 C22 . . 119.6(2)
O6 N7 C22 1 . 119.4(3)
O6 N7 C22 . . 119.4(3)
O8 N8 O7 . . 123.5(3)
O8 N8 C24 . . 118.0(3)
O7 N8 C24 . . 118.5(3)
C6 C1 C2 . . 121.8(2)
C6 C1 Cl1 . . 118.19(19)
C2 C1 Cl1 . . 119.98(19)
C3 C2 C1 . . 117.3(2)
C3 C2 C7 . . 120.8(2)
C1 C2 C7 . . 121.9(2)
C4 C3 C2 . . 121.3(2)
C4 C3 H3 . . 119.4
C2 C3 H3 . . 119.4
C3 C4 C5 . . 120.1(3)
C3 C4 H4 . . 120.0
C5 C4 H4 . . 120.0
C6 C5 C4 . . 120.2(3)
C6 C5 H5 . . 119.9
C4 C5 H5 . . 119.9
C1 C6 C5 . . 119.3(2)
C1 C6 H6A . . 120.3
C5 C6 H6A . . 120.3
N1 C7 C2 . . 120.9(2)
N1 C7 H7 . . 119.6
C2 C7 H7 . . 119.6
N2 C8 C13 . . 120.4(2)
N2 C8 C9 . . 122.8(2)
C13 C8 C9 . . 116.8(2)
C10 C9 C8 . . 121.7(2)
C10 C9 N3 . . 116.1(2)
C8 C9 N3 . . 122.3(2)
C11 C10 C9 . . 118.5(2)
C11 C10 H10 . . 120.7
C9 C10 H10 . . 120.7
C10 C11 C12 . . 122.1(2)
C10 C11 N4 . . 118.6(2)
C12 C11 N4 . . 119.3(2)
C13 C12 C11 . . 119.4(2)
C13 C12 H12 . . 120.3
C11 C12 H12 . . 120.3
C12 C13 C8 . . 121.5(2)
C12 C13 H13 . . 119.3
C8 C13 H13 . . 119.3
C19 C14 C15 . . 121.8(3)
C19 C14 Cl2 . . 117.5(2)
C15 C14 Cl2 . . 120.7(2)
C16 C15 C14 . . 117.1(3)
C16 C15 C20 . . 121.2(3)
C14 C15 C20 . . 121.7(3)
C17 C16 C15 . . 121.6(3)
C17 C16 H16 . . 119.2
C15 C16 H16 . . 119.2
C16 C17 C18 . . 120.0(3)
C16 C17 H17 . . 120.0
C18 C17 H17 . . 120.0
C19 C18 C17 . . 119.8(3)
C19 C18 H18 . . 120.1
C17 C18 H18 . . 120.1
C18 C19 C14 . . 119.7(3)
C18 C19 H19 . . 120.2
C14 C19 H19 . . 120.2
N5 C20 C15 . . 120.2(3)
N5 C20 H20 . . 119.9
C15 C20 H20 . . 119.9
N6 C21 C26 . . 120.1(3)
N6 C21 C22 . . 123.4(2)
C26 C21 C22 . . 116.5(2)
C23 C22 C21 . . 121.7(2)
C23 C22 N7 . . 115.8(2)
C21 C22 N7 . . 122.5(2)
C24 C23 C22 . . 119.3(3)
C24 C23 H23 . . 120.4
C22 C23 H23 . . 120.4
C23 C24 C25 . . 121.1(2)
C23 C24 N8 . . 119.0(3)
C25 C24 N8 . . 119.8(2)
C26 C25 C24 . . 119.9(2)
C26 C25 H25 . . 120.0
C24 C25 H25 . . 120.0
C25 C26 C21 . . 121.4(3)
C25 C26 H26 . . 119.3
C21 C26 H26 . . 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C1 . 1.745(2)
Cl2 C14 . 1.733(3)
O1 N3 . 1.229(3)
O2 N3 . 1.222(3)
O3 N4 . 1.214(3)
O4 N4 . 1.220(3)
O5 N7 . 1.202(3)
O6 N7 . 1.211(3)
O7 N8 . 1.224(3)
O8 N8 . 1.221(3)
N1 C7 . 1.272(3)
N1 N2 . 1.368(3)
N2 C8 . 1.354(3)
N2 H2 . 0.8600
N3 O1 1 1.229(3)
N3 C9 . 1.445(3)
N4 C11 . 1.464(3)
N5 C20 . 1.275(3)
N5 N6 . 1.367(3)
N6 C21 . 1.354(3)
N6 H6 . 0.8600
N7 O6 1 1.211(3)
N7 C22 . 1.443(3)
N8 C24 . 1.456(3)
C1 C6 . 1.377(3)
C1 C2 . 1.396(3)
C2 C3 . 1.389(3)
C2 C7 . 1.457(3)
C3 C4 . 1.375(4)
C3 H3 . 0.9300
C4 C5 . 1.379(4)
C4 H4 . 0.9300
C5 C6 . 1.376(4)
C5 H5 . 0.9300
C6 H6A . 0.9300
C7 H7 . 0.9300
C8 C13 . 1.409(3)
C8 C9 . 1.413(3)
C9 C10 . 1.391(3)
C10 C11 . 1.361(3)
C10 H10 . 0.9300
C11 C12 . 1.385(4)
C12 C13 . 1.367(3)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 C19 . 1.379(4)
C14 C15 . 1.399(4)
C15 C16 . 1.389(4)
C15 C20 . 1.456(4)
C16 C17 . 1.374(4)
C16 H16 . 0.9300
C17 C18 . 1.389(4)
C17 H17 . 0.9300
C18 C19 . 1.372(4)
C18 H18 . 0.9300
C19 H19 . 0.9300
C20 H20 . 0.9300
C21 C26 . 1.410(4)
C21 C22 . 1.414(4)
C22 C23 . 1.380(3)
C23 C24 . 1.362(4)
C23 H23 . 0.9300
C24 C25 . 1.386(4)
C25 C26 . 1.363(4)
C25 H25 . 0.9300
C26 H26 . 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
N6 H6 O6 1 0.86 2.02 2.631(3) 127
N2 H2 O1 1 0.86 2.00 2.622(3) 129
