(<i>E</i>)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine: crystal structure and Hirshfeld surface analysis
Atioğlu, Zeliha; Akkurt, Mehmet; Shikhaliyev, Namiq Q.; Suleymanova, Gulnar T.; Babayeva, Gulnare V.; Gurbanova, Nurana V.; Mammadova, Gunay Z.; Mlowe, Sixberth; Acta Crystallographica Section E 76 (2020) 1291–1295; doi:10.1107/S2056989020009433

data_2243498
_publ_section_title
;
 (<i>E</i>)-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
;
(<i>E</i>)-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 <i>OLEX2</i> (Dolomanov <i>et
al.</i>,  2009)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2016/6</i> (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       '\f and \w 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 <i>x</i> determined using 1032 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  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/[\s^2^(Fo^2^)+(0.0217P)^2^+0.0759P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            vm2237sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2243498
_cod_database_fobs_code          2243498
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.917
_shelx_hkl_checksum              71855
_shelx_res_checksum              52340