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_2023448
_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_absolute_configuration ad
_chemical_formula_iupac          'C15 H12 Br Cl N2 O2'
_chemical_formula_moiety         'C15 H12 Br Cl N2 O2'
_chemical_formula_sum            'C15 H12 Br Cl N2 O2'
_chemical_formula_weight         367.62
_chemical_name_systematic
;
Methyl
(<i>Z</i>)-2-[2-(4-bromophenyl)hydrazin-1-ylidene]-2-(4-chlorophenyl)acetate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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            4
_cell_length_a                   14.0199(16)
_cell_length_b                   16.5940(19)
_cell_length_c                   6.4471(9)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     1499.9(3)
_computing_cell_refinement
;
iMosflm (Battye <i>et al.</i>,  2011)
;
_computing_data_collection
;
Marccd (Doyle, 2011)
;
_computing_data_reduction
;
iMosflm (Battye <i>et al.</i>,  2011)
;
_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 0.983
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.75270
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12123
_diffrn_reflns_theta_full        26.848
_diffrn_reflns_theta_max         30.878
_diffrn_reflns_theta_min         2.014
_exptl_absorpt_coefficient_mu    3.354
_exptl_absorpt_correction_T_max  0.633
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scala; Evans, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.268
_refine_diff_density_min         -0.670
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.167(15)
_refine_ls_extinction_coef       0.0140(10)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0506P)^2^+2.3974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                3677
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5749.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 2023444--2023448.cif.'
_cod_database_code               2023448
_shelx_estimated_absorpt_t_min   0.581
_shelx_estimated_absorpt_t_max   0.668
_shelx_hkl_checksum              41798
_shelx_res_checksum              61759
_shelxl_version_number           .2013