Crystal structures of two hydrazide derivatives of mefenamic acid, 3-(2,3-dimethylanilino)-<i>N</i>'-[(<i>E</i>)-(furan-2-yl)methylidene]benzohydrazide and <i>N</i>'-[(<i>E</i>)-benzylidene]-2-(2,3-dimethylanilino)benzohydrazide
Mohamed, Shaaban K.; Mague, Joel T.; Akkurt, Mehmet; Albayati, Mustafa R.; Elgarhy, Sahar M. I.; Al-Taifi, Elham A.; Acta Crystallographica Section E 77 (2021) 242–246; doi:10.1107/S2056989021001353

data_2243749
_publ_section_title
;
 Crystal structures of two hydrazide derivatives of mefenamic acid,
 3-(2,3-dimethylanilino)-<i>N</i>'-[(<i>E</i>)-(furan-2-yl)methylidene]benzohydrazide
 and
 <i>N</i>'-[(<i>E</i>)-benzylidene]-2-(2,3-dimethylanilino)benzohydrazide
;
_journal_coeditor_code           WM5599
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              242
_journal_page_last               246
_journal_paper_doi               10.1107/S2056989021001353
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C22 H21 N3 O'
_chemical_formula_moiety         'C22 H21 N3 O'
_chemical_formula_sum            'C22 H21 N3 O'
_chemical_formula_weight         343.42
_chemical_name_systematic
;
<i>N</i>'-[(<i>E</i>)-Benzylidene]-2-(2,3-dimethylanilino)-benzohydrazide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 106.285(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3493(8)
_cell_length_b                   15.7501(9)
_cell_length_c                   8.3737(5)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.5746
_cell_measurement_theta_min      4.2641
_cell_volume                     1816.55(18)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>publCIF</i> (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i>  (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13875
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         74.569
_diffrn_reflns_theta_min         4.264
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.155
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL</i> 2016/6 (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0409P)^2^+0.4440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                3140
_reflns_number_total             3665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5599sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243749
_cod_database_fobs_code          2243749
_shelx_estimated_absorpt_t_min   0.894
_shelx_estimated_absorpt_t_max   0.950
_shelx_hkl_checksum              63683
_shelx_res_checksum              17090