#------------------------------------------------------------------------------
#$Date: 2020-07-18 02:48:28 +0300 (Sat, 18 Jul 2020) $
#$Revision: 254395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243498.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_2243498
loop_
_publ_author_name
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Shikhaliyev, Namiq Q.'
'Suleymanova, Gulnar T.'
'Babayeva, Gulnare V.'
'Gurbanova, Nurana V.'
'Mammadova, Gunay Z.'
'Mlowe, Sixberth'
_publ_section_title
;
 (E)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine:
 crystal structure and Hirshfeld surface analysis
;
_journal_coeditor_code           VM2237
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1291
_journal_page_last               1295
_journal_paper_doi               10.1107/S2056989020009433
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C13 H9 Cl2 N3 O2'
_chemical_formula_moiety         'C13 H9 Cl2 N3 O2'
_chemical_formula_sum            'C13 H9 Cl2 N3 O2'
_chemical_formula_weight         310.13
_chemical_name_systematic
;
(E)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 105.940(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1212(14)
_cell_length_b                   12.711(3)
_cell_length_c                   7.6991(16)
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.75
_cell_volume                     670.1(2)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and OLEX2 (Dolomanov et
al.,  2009)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2016/6 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22230
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.443
_diffrn_reflns_theta_min         2.751
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.160
_refine_ls_abs_structure_details
;
Flack x determined using 1032 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0217P)²+0.0759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0635
_reflns_number_gt                2392
_reflns_number_total             2744
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2237sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243498
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.917
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.28649(13) 0.12020(5) 0.58310(10) 0.0583(2) Uani d 1 . .
Cl Cl2 0.28511(15) 0.43809(7) 0.10800(12) 0.0666(3) Uani d 1 . .
O O1 0.3919(5) 0.7625(2) 1.1215(3) 0.0799(8) Uani d 1 . .
O O2 0.2541(5) 0.9024(2) 0.9937(4) 0.0848(9) Uani d 1 . .
N N1 0.3362(4) 0.34075(17) 0.4897(3) 0.0465(6) Uani d 1 . .
H H1N 0.401372 0.310054 0.602708 0.056 Uiso d 1 . .
N N2 0.2806(3) 0.44380(18) 0.4863(3) 0.0397(5) Uani d 1 . .
N N3 0.3101(4) 0.8121(2) 0.9871(4) 0.0531(7) Uani d 1 . .
C C1 0.2672(4) 0.2769(2) 0.3396(4) 0.0365(6) Uani d 1 . .
C C2 0.2365(4) 0.1696(2) 0.3645(4) 0.0411(7) Uani d 1 . .
C C3 0.1710(5) 0.1009(2) 0.2220(4) 0.0543(8) Uani d 1 . .
H H3A 0.152757 0.030205 0.243822 0.065 Uiso calc 1 . .
C C4 0.1330(5) 0.1370(3) 0.0483(5) 0.0588(9) Uani d 1 . .
H H4A 0.086569 0.091344 -0.048297 0.071 Uiso calc 1 . .
C C5 0.1641(5) 0.2419(3) 0.0174(4) 0.0558(8) Uani d 1 . .
H H5A 0.139312 0.266660 -0.100398 0.067 Uiso calc 1 . .
C C6 0.2322(4) 0.3105(2) 0.1614(4) 0.0426(7) Uani d 1 . .
C C7 0.3439(5) 0.4963(2) 0.6318(4) 0.0413(7) Uani d 1 . .
H H7A 0.421014 0.463484 0.734710 0.050 Uiso calc 1 . .
C C8 0.2957(4) 0.6082(2) 0.6376(3) 0.0359(6) Uani d 1 . .
C C9 0.2219(5) 0.6675(2) 0.4811(4) 0.0433(7) Uani d 1 . .
H H9A 0.201931 0.635668 0.368765 0.052 Uiso calc 1 . .
C C10 0.1784(5) 0.7724(2) 0.4908(4) 0.0512(8) Uani d 1 . .
H H10A 0.131772 0.810787 0.384850 0.061 Uiso calc 1 . .
C C11 0.2029(5) 0.8214(2) 0.6557(4) 0.0475(7) Uani d 1 . .
H H11A 0.169393 0.891678 0.662994 0.057 Uiso calc 1 . .
C C12 0.2790(4) 0.7623(2) 0.8092(4) 0.0387(6) Uani d 1 . .
C C13 0.3274(4) 0.6576(2) 0.8048(4) 0.0375(6) Uani d 1 . .
H H13A 0.380225 0.620594 0.911236 0.045 Uiso calc 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'
Cl Cl 0.1484 0.1585 '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'
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
N2 N1 C1 . . 120.7(2) ?
N2 N1 H1N . . 118.5 ?
C1 N1 H1N . . 119.7 ?
C7 N2 N1 . . 117.0(2) ?
O1 N3 O2 . . 122.6(3) ?
O1 N3 C12 . . 119.0(3) ?
O2 N3 C12 . . 118.5(3) ?
N1 C1 C6 . . 124.6(2) ?
N1 C1 C2 . . 119.2(3) ?
C6 C1 C2 . . 116.1(2) ?
C3 C2 C1 . . 122.5(3) ?
C3 C2 Cl1 . . 118.4(2) ?
C1 C2 Cl1 . . 119.0(2) ?
C4 C3 C2 . . 119.9(3) ?
C4 C3 H3A . . 120.1 ?
C2 C3 H3A . . 120.1 ?
C3 C4 C5 . . 119.6(3) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
C5 C6 C1 . . 121.5(3) ?
C5 C6 Cl2 . . 116.6(2) ?
C1 C6 Cl2 . . 121.8(2) ?
N2 C7 C8 . . 120.4(3) ?
N2 C7 H7A . . 119.8 ?
C8 C7 H7A . . 119.8 ?
C13 C8 C9 . . 118.7(2) ?
C13 C8 C7 . . 119.0(2) ?
C9 C8 C7 . . 122.2(2) ?
C10 C9 C8 . . 120.9(3) ?
C10 C9 H9A . . 119.5 ?
C8 C9 H9A . . 119.5 ?
C9 C10 C11 . . 120.9(3) ?
C9 C10 H10A . . 119.6 ?
C11 C10 H10A . . 119.6 ?
C12 C11 C10 . . 117.5(3) ?
C12 C11 H11A . . 121.2 ?
C10 C11 H11A . . 121.2 ?
C13 C12 C11 . . 123.2(2) ?
C13 C12 N3 . . 117.7(3) ?
C11 C12 N3 . . 119.1(2) ?
C12 C13 C8 . . 118.7(2) ?
C12 C13 H13A . . 120.7 ?
C8 C13 H13A . . 120.7 ?
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 C2 . 1.739(3) ?
Cl2 C6 . 1.740(3) ?
O1 N3 . 1.215(4) ?
O2 N3 . 1.220(4) ?
N1 N2 . 1.367(3) ?
N1 C1 . 1.387(3) ?
N1 H1N . 0.9500 ?
N2 C7 . 1.275(3) ?
N3 C12 . 1.469(3) ?
C1 C6 . 1.392(4) ?
C1 C2 . 1.404(4) ?
C2 C3 . 1.379(4) ?
C3 C4 . 1.369(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.383(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.389(4) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.467(4) ?
C7 H7A . 0.9300 ?
C8 C13 . 1.393(3) ?
C8 C9 . 1.396(4) ?
C9 C10 . 1.375(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.382(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.379(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.378(4) ?
C13 H13A . 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
_geom_hbond_publ_flag
N1 H1N Cl1 1_555 0.95 2.54 2.940(2) 106 yes
N1 H1N O1 2_647 0.95 2.31 3.243(3) 168 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C7 . . . . 177.3(3) ?
N2 N1 C1 C6 . . . . 35.6(4) ?
N2 N1 C1 C2 . . . . -147.1(3) ?
N1 C1 C2 C3 . . . . -179.0(3) ?
C6 C1 C2 C3 . . . . -1.5(4) ?
N1 C1 C2 Cl1 . . . . -0.1(4) ?
C6 C1 C2 Cl1 . . . . 177.4(2) ?
C1 C2 C3 C4 . . . . -0.2(5) ?
Cl1 C2 C3 C4 . . . . -179.1(3) ?
C2 C3 C4 C5 . . . . 1.2(5) ?
C3 C4 C5 C6 . . . . -0.4(5) ?
C4 C5 C6 C1 . . . . -1.4(5) ?
C4 C5 C6 Cl2 . . . . 175.0(3) ?
N1 C1 C6 C5 . . . . 179.6(3) ?
C2 C1 C6 C5 . . . . 2.3(4) ?
N1 C1 C6 Cl2 . . . . 3.4(4) ?
C2 C1 C6 Cl2 . . . . -173.9(2) ?
N1 N2 C7 C8 . . . . 178.2(2) ?
N2 C7 C8 C13 . . . . 165.5(3) ?
N2 C7 C8 C9 . . . . -15.6(4) ?
C13 C8 C9 C10 . . . . -1.0(4) ?
C7 C8 C9 C10 . . . . -179.9(3) ?
C8 C9 C10 C11 . . . . -1.3(5) ?
C9 C10 C11 C12 . . . . 2.3(5) ?
C10 C11 C12 C13 . . . . -1.2(4) ?
C10 C11 C12 N3 . . . . 179.1(3) ?
O1 N3 C12 C13 . . . . 6.2(4) ?
O2 N3 C12 C13 . . . . -174.4(3) ?
O1 N3 C12 C11 . . . . -174.0(3) ?
O2 N3 C12 C11 . . . . 5.4(4) ?
C11 C12 C13 C8 . . . . -1.0(4) ?
N3 C12 C13 C8 . . . . 178.8(3) ?
C9 C8 C13 C12 . . . . 2.0(4) ?
C7 C8 C13 C12 . . . . -179.0(3) ?

_cod_database_fobs_code 2243498
