Synthesis, X-ray crystal structure, Hirshfeld surface analysis and DFT studies of (<i>E</i>)-<i>N</i>'-(2-bromobenzylidene)-4-methylbenzohydrazide
Anitha, Azhagan Ganapathi; Arunagiri, Chidambaram; Subashini, Annamalai; Acta Crystallographica Section E 75 (2019) 109–114; doi:10.1107/S2056989018017978

data_2242819
_publ_section_title
;
 Synthesis, X-ray crystal structure, Hirshfeld surface analysis and DFT
 studies of
 (<i>E</i>)-<i>N</i>'-(2-bromobenzylidene)-4-methylbenzohydrazide
;
_journal_coeditor_code           LH5887
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              109
_journal_page_last               114
_journal_paper_doi               10.1107/S2056989018017978
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C15 H13 Br N2 O'
_chemical_formula_moiety         'C15 H13 Br N2 O'
_chemical_formula_sum            'C15 H13 Br N2 O'
_chemical_formula_weight         317.18
_chemical_name_common
;
(<i>E</i>)-<i>N</i>'-(2-Bromobenzylidene)-4-methylbenzohydrazide
;
_chemical_name_systematic
;
(<i>E</i>)-4-Methyl-<i>N</i>'-(2-bromobenzylidene)benzohydrazide
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6002(10)
_cell_length_b                   11.5584(13)
_cell_length_c                   12.5823(12)
_cell_measurement_reflns_used    6594
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.39
_cell_volume                     1396.2(3)
_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
;
ORTEP3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare <i>et al.</i>,  1999)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17816
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    2.937
_exptl_absorpt_correction_T_max  0.5911
_exptl_absorpt_correction_T_min  0.4728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.468
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0365
_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/[\s^2^(Fo^2^)+(0.0208P)^2^+2.2419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                1837
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lh5887sup1.cif
_cod_data_source_block           I
_cod_database_code               2242819