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_2023445
_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          'C17 H17 Br N2 O2'
_chemical_formula_moiety         'C17 H17 Br N2 O2'
_chemical_formula_sum            'C17 H17 Br N2 O2'
_chemical_formula_weight         361.23
_chemical_name_systematic
;
Methyl
(<i>Z</i>)-2-(4-bromophenyl)-2-[2-(3,5-dimethylphenyl)hydrazin-1-ylidene]acetate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                83.480(9)
_cell_angle_beta                 73.266(7)
_cell_angle_gamma                81.695(8)
_cell_formula_units_Z            4
_cell_length_a                   9.8859(9)
_cell_length_b                   12.3021(11)
_cell_length_c                   13.9790(12)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      1.8
_cell_volume                     1606.4(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 0.990
_diffrn_measured_fraction_theta_max 0.971
_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21921
_diffrn_reflns_theta_full        26.848
_diffrn_reflns_theta_max         31.072
_diffrn_reflns_theta_min         1.777
_exptl_absorpt_coefficient_mu    2.967
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Scala; Evans, 2006)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.887
_refine_diff_density_min         -0.942
_refine_ls_extinction_coef       0.044(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2019/2 (Sheldrick, 2015a)
;
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         8417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1079P)^2^+1.6265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1902
_reflns_number_gt                6338
_reflns_number_total             8417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5749.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 2023444--2023448.cif.'
_cod_database_code               2023445
_shelx_estimated_absorpt_t_min   0.717
_shelx_estimated_absorpt_t_max   0.819
_shelx_hkl_checksum              9212
_shelx_res_checksum              79377