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_2022762
_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          'C18 H16 F N3 O'
_chemical_formula_moiety         'C18 H16 F N3 O'
_chemical_formula_sum            'C18 H16 F N3 O'
_chemical_formula_weight         309.34
_chemical_name_systematic
(<i>E</i>)-4-[(4-Fluorobenzylidene)amino]-1,5-dimethyl-2-phenyl-1<i>H</i>-pyrazol-3(2<i>H</i>)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7886(13)
_cell_length_b                   16.6007(3)
_cell_length_c                   26.9563(8)
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_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      72.96
_cell_measurement_theta_min      5.32
_cell_volume                     3037.9(6)
_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)
;
_computing_publication_material
;
<i>SHELXL2018/3</i> (Sheldrick, 2015), PLATON (Spek, 2020) and
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015)
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Superflip (Palatinus & Chapuis, 2007; JANA2006 (Pet\<r\'i\<cek <i>et
al.</i>,  2014)
;
_diffrn_ambient_temperature      95(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2027
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_k_min       -20
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_exptl_absorpt_correction_T_min  0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.211
_refine_ls_extinction_coef       0.0025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
(<i>SHELXL2018/3</i>; Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.048
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_refine_ls_number_parameters     211
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0413P)^2^+0.3986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                2346
_reflns_number_total             3041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb8065sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2022761--2022762.cif.'
_cod_database_code               2022762
_cod_database_fobs_code          2022762
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.997
_shelx_hkl_checksum              34674
_shelx_res_checksum              41808