Crystal structure, Hirshfeld surface analysis and DFT study of <i>N</i>-(2-amino-5-methylphenyl)-2-(5-methyl-1<i>H</i>-pyrazol-3-yl)acetamide
Al Ati, Gamal; Chkirate, Karim; Mague, Joel T.; Abad, Nadeem; Achour, Redouane; Essassi, El Mokhtar; Acta Crystallographica Section E 77 (2021) 638–642; doi:10.1107/S205698902100503X

data_2243827
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT study of
 <i>N</i>-(2-amino-5-methylphenyl)-2-(5-methyl-1<i>H</i>-pyrazol-3-yl)acetamide
;
_journal_coeditor_code           DJ2025
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              638
_journal_page_last               642
_journal_paper_doi               10.1107/S205698902100503X
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C13 H16 N4 O'
_chemical_formula_moiety         'C13 H16 N4 O'
_chemical_formula_sum            'C13 H16 N4 O'
_chemical_formula_weight         244.30
_chemical_name_systematic
;
<i>N</i>-(2-Amino-5-methylphenyl)-2-(5-methyl-1<i>H</i>-pyrazol-3-yl)acetamide
;
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 94.6830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1271(3)
_cell_length_b                   8.9295(3)
_cell_length_c                   19.2508(7)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.3581
_cell_measurement_theta_min      2.5159
_cell_volume                     1221.06(8)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2020)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2020)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2020)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018/1</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 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 3 diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            66426
_diffrn_reflns_theta_full        34.350
_diffrn_reflns_theta_max         34.361
_diffrn_reflns_theta_min         2.516
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.227
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.8885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1643
_reflns_number_gt                4794
_reflns_number_total             5120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dj2025sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243827
_cod_database_fobs_code          2243827
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.986
_shelx_hkl_checksum              63538
_shelx_res_checksum              94292