Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations
Saeed, Aamer; Khurshid, Asma; Flörke, Ulrich; Echeverría, Gustavo A.; Piro, Oscar E.; Gil, Diego M.; Rocha, Mariana; Frontera, Antonio; El-Seedi, Hesham R.; Mumtaz, Amara; Erben, Mauricio F.; New Journal of Chemistry 44 (2020) 19541–19554; doi:10.1039/D0NJ03958F

data_7060131
_publ_section_title
;
 Intermolecular interactions in antipyrine-like derivatives
 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides:
 X-ray structure, Hirshfeld surface analysis and DFT calculations
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19541
_journal_page_last               19554
_journal_paper_doi               10.1039/D0NJ03958F
_journal_volume                  44
_journal_year                    2020
_chemical_formula_sum            'C18 H16 Cl N3 O2'
_chemical_formula_weight         341.79
_chemical_name_systematic
2-chloro-N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide
_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-2018/3
_audit_update_record
;
2020-07-18 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.334(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9852(11)
_cell_length_b                   6.2373(4)
_cell_length_c                   20.2255(12)
_cell_measurement_reflns_used    1516
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      69.8380
_cell_measurement_theta_min      4.5390
_cell_volume                     1701.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6646
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.347
_diffrn_reflns_theta_min         4.534
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Aqueous ethanol'
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.2432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1518
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2219
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03958f2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060131
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              21302