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_7060130
_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_moiety         'C18 H16 Br N3 O2'
_chemical_formula_sum            'C18 H16 Br N3 O2'
_chemical_formula_weight         386.25
_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_block_doi                 10.5517/ccdc.csd.cc217l85
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-12-08 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.055(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1326(15)
_cell_length_b                   6.1144(6)
_cell_length_c                   20.190(2)
_cell_measurement_reflns_used    4327
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      2.89
_cell_volume                     1676.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15171
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         1.499
_exptl_absorpt_coefficient_mu    2.467
_exptl_absorpt_correction_T_max  0.6651
_exptl_absorpt_correction_T_min  0.4099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0515P)^2^+0.2466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3323
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03958f2.cif
_cod_data_source_block           s2079
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060130
_shelxl_version_number           2013-4
_shelx_res_checksum              22671