Crystal structures and Hirshfeld surface analyses of methyl (2<i>Z</i>)-(4-bromo-phen-yl)[2-(4-methyl-phen-yl)hydrazinyl-idene]acetate, methyl (2<i>Z</i>)-(4-bromophen-yl)[2-(3,5-di-methyl-phen-yl)hydrazinyl-idene]acetate, methyl (2<i>Z</i>)-[2-(4-meth-oxy-phen-yl)hydrazinyl-idene](3-nitro-phen-yl)acetate, methyl (2<i>E</i>)-(4-chlorophen-yl)(2-phenyl-hydrazinyl-idene)acetate and methyl (2<i>Z</i>)-[2-(4-bromo-phen-yl)hydrazinylidene](4-chloro-phen-yl)acetate.
Shikhaliyev, Namiq Q.; Babazade, Aliyar A.; Atakishiyeva, Gulnar T.; Shikhaliyeva, Irada M.; Maharramov, Abel M.; Khrustalev, Victor N.; Atioğlu, Zeliha; Akkurt, Mehmet; Bhattarai, Ajaya; Acta crystallographica. Section E, Crystallographic communications 81 (2025) 314–323; doi:10.1107/S2056989025002051

data_2023444
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of methyl
 (2<i>Z</i>)-(4-bromo-phen-yl)[2-(4-methyl-phen-yl)hydrazinyl-idene]acetate,
 methyl
 (2<i>Z</i>)-(4-bromophen-yl)[2-(3,5-di-methyl-phen-yl)hydrazinyl-idene]acetate,
 methyl
 (2<i>Z</i>)-[2-(4-meth-oxy-phen-yl)hydrazinyl-idene](3-nitro-phen-yl)acetate,
 methyl (2<i>E</i>)-(4-chlorophen-yl)(2-phenyl-hydrazinyl-idene)acetate
 and methyl
 (2<i>Z</i>)-[2-(4-bromo-phen-yl)hydrazinylidene](4-chloro-phen-yl)acetate.
;
_journal_coeditor_code           WM5749
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              314
_journal_page_last               323
_journal_paper_doi               10.1107/S2056989025002051
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C16 H15 Br N2 O2'
_chemical_formula_moiety         'C16 H15 Br N2 O2'
_chemical_formula_sum            'C16 H15 Br N2 O2'
_chemical_formula_weight         347.20
_chemical_name_systematic
;
Methyl
(<i>Z</i>)-2-(4-bromophenyl)-2-[2-(4-methylphenyl)hydrazin-1-ylidene]acetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 109.8598(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.6329(5)
_cell_length_b                   4.84061(6)
_cell_length_c                   19.1365(3)
_cell_measurement_reflns_used    15931
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.103
_cell_measurement_theta_min      2.692
_cell_volume                     3017.33(8)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30865
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.029
_diffrn_reflns_theta_min         2.713
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.766
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.169
_refine_diff_density_min         -1.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0672P)^2^+8.4257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                3031
_reflns_number_total             3282
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5749.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 2023444--2023448.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2023444
_shelx_estimated_absorpt_t_min   0.520
_shelx_estimated_absorpt_t_max   0.895
_shelx_hkl_checksum              9023
_shelx_res_checksum              37133
_shelxl_version_number           .2013