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_2023446
_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 N3 O5'
_chemical_formula_moiety         'C16 H15 N3 O5'
_chemical_formula_sum            'C16 H15 N3 O5'
_chemical_formula_weight         329.31
_chemical_name_systematic
;
Methyl
(<i>Z</i>)-2-[2-(4-methoxyphenyl)hydrazin-1-ylidene]-2-(3-nitrophenyl)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                 96.156(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8022(5)
_cell_length_b                   21.9649(6)
_cell_length_c                   7.43092(15)
_cell_measurement_reflns_used    4042
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.232
_cell_measurement_theta_min      4.026
_cell_volume                     3051.19(13)
_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 0.988
_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  0.0724
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            21181
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.023
_diffrn_reflns_theta_min         3.104
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       'prismatic needle'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.252
_refine_ls_extinction_coef       0.00022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0486P)^2^+2.64P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1260
_reflns_number_gt                2634
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5749.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 2023444--2023448.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2023446
_shelx_estimated_absorpt_t_min   0.777
_shelx_estimated_absorpt_t_max   0.922
_shelx_hkl_checksum              38364
_shelx_res_checksum              79511
_shelxl_version_number           .2013