Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1<i>H</i>-1,3-benzodiazol-2-one
Saber, Asmaa; Srhir, Mohamed; Hökelek, Tuncer; Mague, Joel T.; Hamou Ahabchane, Noureddine; Sebbar, Nada Kheira; Essassi, El Mokhtar; Acta Crystallographica Section E 75 (2019) 1940–1946; doi:10.1107/S2056989019015779

data_2243209
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy and
 DFT studies of
 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1<i>H</i>-1,3-benzodiazol-2-one
;
_journal_coeditor_code           LH5936
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1940
_journal_page_last               1946
_journal_paper_doi               10.1107/S2056989019015779
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C11 H10 N2 O'
_chemical_formula_moiety         'C11 H10 N2 O'
_chemical_formula_sum            'C11 H10 N2 O'
_chemical_formula_weight         186.21
_chemical_name_systematic
;
1-Methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1<i>H</i>-1,3-benzodiazol-2-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.914(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1507(3)
_cell_length_b                   8.8177(4)
_cell_length_c                   15.4602(7)
_cell_measurement_reflns_used    5848
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.1025
_cell_measurement_theta_min      5.7788
_cell_volume                     965.52(7)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018</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 10.4167
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6896
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.122
_diffrn_reflns_theta_min         5.779
_diffrn_source                   'INCOATEC I\mS micro-focus source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.189
_refine_ls_extinction_coef       0.0100(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0402P)^2^+0.2239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0856
_reflns_number_gt                1679
_reflns_number_total             1812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5936sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243209
_cod_database_fobs_code          2243209
_shelx_estimated_absorpt_t_min   0.810
_shelx_estimated_absorpt_t_max   0.924
_shelx_hkl_checksum              32795
_shelx_res_checksum              56470