Synthesis, crystal structure, Hirshfeld surface analysis and experimental and theoretical study of new azo compound methyl 2-{2-[(E)-2-oxo-1,2-dihydronaphthalen-1-ylidene]hydrazin-1-yl}benzoate.
Chetioui, Souheyla; Khelloul, Nawel; Boukabcha, Nourdine; Benhalima, Nadia; Smati, Sabrina; Drim, Khaled; Chouaih, Abdelkader; Acta crystallographica. Section C, Structural chemistry 81 (2025) –; doi:10.1107/S2053229625003523

data_2312850
_publ_section_title
;
 Synthesis, crystal structure, Hirshfeld surface analysis and experimental
 and theoretical study of new azo compound methyl
 2-{2-[(E)-2-oxo-1,2-dihydronaphthalen-1-ylidene]hydrazin-1-yl}benzoate.
;
_journal_coeditor_code           SON3005
_journal_issue                   6
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229625003523
_journal_volume                  81
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesised by authors, see text'
_chemical_formula_iupac          'C18 H14 N2 O3'
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31
_chemical_name_systematic
;
Methyl
2-{2-[(<i>E</i>)-2-oxo-1,2-dihydronaphthalen-1-ylidene]hydrazin-1-yl}benzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.138(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.200(6)
_cell_length_b                   16.244(10)
_cell_length_c                   8.058(5)
_cell_measurement_reflns_used    2191
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.51
_cell_volume                     1463.8(15)
_computing_cell_refinement
;
APEX2 (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
APEX2 (Bruker, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and <i>CrystalExplorer3.0</i> (Wolff <i>et
al.</i>,  2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11105
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.097
_diffrn_reflns_theta_min         1.821
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0748P)^2^+0.3794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                2137
_reflns_number_total             3493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            son3005sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312850
_shelx_hkl_checksum              17327
_shelx_res_checksum              26392
_cod_database_fobs_code 2312850