Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-chloroethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate
Hayani, Sonia; Filali Baba, Yassir; Hökelek, Tuncer; Ouazzani Chahdi, Fouad; Mague, Joel T.; Sebbar, Nada Kheira; Kandri Rodi, Youssef; Acta Crystallographica Section E 75 (2019) 1411–1417; doi:10.1107/S2056989019012283

data_2243080
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy and
 DFT studies of 2-chloroethyl
 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate
;
_journal_coeditor_code           LH5918
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1411
_journal_page_last               1417
_journal_paper_doi               10.1107/S2056989019012283
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C15 H12 Cl N O3'
_chemical_formula_moiety         'C15 H12 Cl N O3'
_chemical_formula_sum            'C15 H12 Cl N O3'
_chemical_formula_weight         289.71
_chemical_name_systematic
;
2-Chloroethyl
2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 92.784(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1809(2)
_cell_length_b                   21.4466(5)
_cell_length_c                   8.9173(2)
_cell_measurement_reflns_used    6719
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.868
_cell_measurement_theta_min      4.122
_cell_volume                     1371.70(6)
_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 0.987
_diffrn_measured_fraction_theta_max 0.983
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10119
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.067
_diffrn_reflns_theta_min         4.123
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    2.532
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.64
_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    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0783
_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^)+(0.0332P)^2^+4.0657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1725
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                2170
_reflns_number_total             2555
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5918sup1.cif
_cod_data_source_block           I
_cod_database_code               2243080
_cod_database_fobs_code          2243080
_shelx_estimated_absorpt_t_min   0.642
_shelx_estimated_absorpt_t_max   0.975
_shelx_hkl_checksum              62051
_shelx_res_checksum              40046