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_2023447
_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          'C15 H13 Cl N2 O2'
_chemical_formula_moiety         'C15 H13 Cl N2 O2'
_chemical_formula_sum            'C15 H13 Cl N2 O2'
_chemical_formula_weight         288.72
_chemical_name_systematic
;
Methyl (<i>E</i>)-2-(4-chlorophenyl)-2-(2-phenylhydrazin-1-ylidene)acetate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.86326(8)
_cell_length_b                   8.79608(3)
_cell_length_c                   19.24680(8)
_cell_measurement_reflns_used    35974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.486
_cell_measurement_theta_min      4.588
_cell_volume                     2685.59(2)
_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 0.999
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            51407
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.104
_diffrn_reflns_theta_min         4.595
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.547
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+1.4066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                2871
_reflns_number_total             2935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5749.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 2023444--2023448.cif.'
_cod_database_code               2023447
_shelx_estimated_absorpt_t_min   0.750
_shelx_estimated_absorpt_t_max   0.862
_shelx_hkl_checksum              91984
_shelx_res_checksum              71331
_shelxl_version_number           .2013