Syntheses, crystal structures, Hirshfeld surface analyses and energy frameworks of two 4-amino-anti-pyrine Schiff base compounds: (<i>E</i>)-4-{[4-(di-ethyl-amino)-benzyl-idene]amino}-1,5-dimethyl-2-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one and (<i>E</i>)-4-[(4-fluoro-benzyl-idene)amino]-1,5-dimethyl-2-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one.
Shankar, M. G.; Kumaravel, R.; Subashini, A.; Ramamurthi, K.; Kučeráková, Monika; Dušek, Michal; Stoeckli-Evans, Helen; Acta crystallographica. Section E, Crystallographic communications 79 (2023) 538–544; doi:10.1107/S2056989023004085

data_2022761
_publ_section_title
;
 Syntheses, crystal structures, Hirshfeld surface analyses and energy
 frameworks of two 4-amino-anti-pyrine Schiff base compounds:
 (<i>E</i>)-4-{[4-(di-ethyl-amino)-benzyl-idene]amino}-1,5-dimethyl-2-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one
 and
 (<i>E</i>)-4-[(4-fluoro-benzyl-idene)amino]-1,5-dimethyl-2-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one.
;
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              538
_journal_page_last               544
_journal_paper_doi               10.1107/S2056989023004085
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C22 H26 N4 O'
_chemical_formula_moiety         'C22 H26 N4 O'
_chemical_formula_sum            'C22 H26 N4 O'
_chemical_formula_weight         362.47
_chemical_name_systematic
(<i>E</i>)-4-{[4-(Diethylamino)benzylidene]amino}-1,5-dimethyl-2-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 102.338(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1588(7)
_cell_length_b                   7.0910(3)
_cell_length_c                   32.1594(10)
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_cell_measurement_temperature    120(2)
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_cell_measurement_theta_min      4.22
_cell_volume                     3822.6(3)
_computing_cell_refinement
;
CrysAlisPro (Agilent, 2010)
;
_computing_data_collection
;
CrysAlisPro (Agilent, 2010)
;
_computing_data_reduction
;
CrysAlisPro (Agilent, 2010)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020) and Mercury (Macrae <i>et al.</i>,  2020)
;
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;
<i>SHELXL2018/3</i> (Sheldrick, 2015), PLATON (Spek, 2020) and
publcif (Westrip, 2010)
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_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007; JANA2006 (Pet\<r\'i\<cek <i>et
al.</i>,  2014)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0228
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_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
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_diffrn_reflns_limit_l_min       -32
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_diffrn_reflns_theta_max         67.115
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_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2010)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
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_exptl_crystal_size_mid          0.2633
_exptl_crystal_size_min          0.0789
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0498P)^2^+1.7059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                2946
_reflns_number_total             3401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb8065sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2022761--2022762.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022761
_cod_database_fobs_code          2022761
_shelx_hkl_checksum              55896
_shelx_res_checksum              59255