Crystal structure, Hirshfeld surface analysis and frontier molecular orbital analysis of (<i>E</i>)-4-bromo-<i>N</i>'-(2,3-dichlorobenzylidene)benzohydrazide
Sivajeyanthi, Palaniyappan; Jeevaraj, Muthaiah; Edison, Bellarmin; Balasubramani, Kasthuri; Acta Crystallographica Section E 75 (2019) 324–327; doi:10.1107/S2056989019001816

data_2242847
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and frontier molecular
 orbital analysis of
 (<i>E</i>)-4-bromo-<i>N</i>'-(2,3-dichlorobenzylidene)benzohydrazide
;
_journal_coeditor_code           SU5466
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              324
_journal_page_last               327
_journal_paper_doi               10.1107/S2056989019001816
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H9 Br Cl2 N2 O'
_chemical_formula_moiety         'C14 H9 Br Cl2 N2 O'
_chemical_formula_sum            'C14 H9 Br Cl2 N2 O'
_chemical_formula_weight         372.04
_chemical_name_systematic
;
(<i>E</i>)-4-Bromo-<i>N</i>'-(2,3-dichlorobenzylidene)benzohydrazide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 96.446(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1952(18)
_cell_length_b                   14.055(2)
_cell_length_c                   9.3050(12)
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      47.530
_cell_measurement_theta_min      4.666
_cell_volume                     1454.9(4)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1993)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11392
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.251
_diffrn_reflns_theta_min         2.637
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.188
_exptl_absorpt_correction_T_max  0.568
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.630
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0511
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1731
_reflns_number_gt                1724
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5466sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1454.8(4)
_cod_database_code               2242847
_cod_database_fobs_code          2242847
_shelx_estimated_absorpt_t_min   0.448
_shelx_estimated_absorpt_t_max   0.568
_shelx_hkl_checksum              14069
_shelx_res_checksum              98578