#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546641.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1546641
loop_
_publ_author_name
'Filali Baba, Yassir'
'Kandri Rodi, Youssef'
'Jasinski, Jerry P.'
'Kaur, Manpreet'
'Ouzidan, Younes'
'Essassi, El Mokhtar'
_publ_section_title
;
 Prop-2-ynyl 2-oxo-1-(prop-2-ynyl)-1,2-dihydroquinoline-4-carboxylate
;
_journal_coeditor_code           VM4026
_journal_issue                   7
_journal_name_full               IUCrData
_journal_page_first              x171072
_journal_paper_doi               10.1107/S2414314617010720
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C16 H11 N O3'
_chemical_formula_moiety         'C16 H11 N O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26
_chemical_name_systematic
;
Prop-2-ynyl 2-oxo-1-(prop-2-ynyl)-1,2-dihydroquinoline-4-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                91.059(11)
_cell_angle_beta                 107.867(12)
_cell_angle_gamma                109.814(14)
_cell_formula_units_Z            2
_cell_length_a                   7.3070(11)
_cell_length_b                   8.7763(13)
_cell_length_c                   11.2927(13)
_cell_measurement_reflns_used    943
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1840
_cell_measurement_theta_min      4.1210
_cell_volume                     642.36(18)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.006
_diffrn_reflns_theta_min         4.152
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0487
_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/[σ²(Fo²)+(0.0621P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                1624
_reflns_number_total             2418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm4026sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        642.36(17)
_cod_database_code               1546641
_cod_database_fobs_code          1546641
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.0174(3) 0.0643(2) 0.29315(16) 0.0698(5) Uani d 1
O O2 0.3186(3) 0.4028(2) 0.79834(14) 0.0621(5) Uani d 1
O O3 0.4300(2) 0.2141(2) 0.74109(13) 0.0568(4) Uani d 1
N N1 0.0822(3) 0.3367(2) 0.32712(15) 0.0455(4) Uani d 1
C C1 0.0936(3) 0.1917(3) 0.3668(2) 0.0499(5) Uani d 1
C C2 0.1935(3) 0.1990(3) 0.5004(2) 0.0497(5) Uani d 1
H H2 0.2045 0.1041 0.5317 0.060 Uiso calc 1
C C3 0.2707(3) 0.3380(3) 0.58080(18) 0.0433(5) Uani d 1
C C4 0.2700(3) 0.4906(3) 0.53617(18) 0.0418(5) Uani d 1
C C5 0.3604(3) 0.6417(3) 0.6127(2) 0.0513(5) Uani d 1
H H5 0.4252 0.6466 0.6984 0.062 Uiso calc 1
C C6 0.3554(4) 0.7834(3) 0.5639(2) 0.0585(6) Uani d 1
H H6 0.4145 0.8827 0.6163 0.070 Uiso calc 1
C C7 0.2618(4) 0.7773(3) 0.4359(2) 0.0571(6) Uani d 1
H H7 0.2576 0.8728 0.4029 0.068 Uiso calc 1
C C8 0.1753(3) 0.6319(3) 0.3576(2) 0.0507(5) Uani d 1
H H8 0.1163 0.6300 0.2717 0.061 Uiso calc 1
C C9 0.1753(3) 0.4868(3) 0.40563(19) 0.0424(5) Uani d 1
C C10 0.3424(3) 0.3264(3) 0.71837(19) 0.0477(5) Uani d 1
C C11 0.4825(4) 0.1777(3) 0.8687(2) 0.0624(6) Uani d 1
H H11A 0.3585 0.1216 0.8886 0.075 Uiso calc 1
H H11B 0.5623 0.2777 0.9271 0.075 Uiso calc 1
C C12 0.6031(4) 0.0739(3) 0.8771(2) 0.0645(7) Uani d 1
C C13 0.7044(5) -0.0037(4) 0.8812(3) 0.0873(10) Uani d 1
H H13 0.7860 -0.0661 0.8845 0.105 Uiso calc 1
C C14 -0.0384(3) 0.3270(3) 0.19428(19) 0.0534(6) Uani d 1
H H14A -0.1455 0.2193 0.1664 0.064 Uiso calc 1
H H14B -0.1052 0.4066 0.1867 0.064 Uiso calc 1
C C15 0.0878(4) 0.3570(3) 0.1123(2) 0.0546(6) Uani d 1
C C16 0.1826(5) 0.3752(4) 0.0445(2) 0.0720(7) Uani d 1
H H16 0.2586 0.3898 -0.0098 0.086 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 O3 C11 115.86(16)
C1 N1 C9 123.77(18)
C1 N1 C14 116.01(19)
C9 N1 C14 120.21(18)
O1 C1 N1 121.4(2)
O1 C1 C2 122.9(2)
N1 C1 C2 115.6(2)
C1 C2 H2 118.8
C3 C2 C1 122.5(2)
C3 C2 H2 118.8
C2 C3 C4 120.96(19)
C2 C3 C10 117.7(2)
C4 C3 C10 121.16(19)
C5 C4 C3 124.25(19)
C5 C4 C9 118.2(2)
C9 C4 C3 117.50(19)
C4 C5 H5 119.3
C6 C5 C4 121.3(2)
C6 C5 H5 119.3
C5 C6 H6 120.2
C5 C6 C7 119.6(2)
C7 C6 H6 120.2
C6 C7 H7 119.6
C8 C7 C6 120.7(2)
C8 C7 H7 119.6
C7 C8 H8 119.8
C7 C8 C9 120.5(2)
C9 C8 H8 119.8
N1 C9 C4 119.30(19)
C8 C9 N1 121.09(19)
C8 C9 C4 119.6(2)
O2 C10 O3 123.80(19)
O2 C10 C3 125.2(2)
O3 C10 C3 110.91(17)
O3 C11 H11A 110.4
O3 C11 H11B 110.4
O3 C11 C12 106.68(18)
H11A C11 H11B 108.6
C12 C11 H11A 110.4
C12 C11 H11B 110.4
C13 C12 C11 176.9(3)
C12 C13 H13 180.0
N1 C14 H14A 109.0
N1 C14 H14B 109.0
H14A C14 H14B 107.8
C15 C14 N1 112.87(18)
C15 C14 H14A 109.0
C15 C14 H14B 109.0
C16 C15 C14 177.4(3)
C15 C16 H16 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.229(3)
O2 C10 1.203(2)
O3 C10 1.336(3)
O3 C11 1.444(2)
N1 C1 1.378(3)
N1 C9 1.401(3)
N1 C14 1.472(3)
C1 C2 1.450(3)
C2 H2 0.9300
C2 C3 1.345(3)
C3 C4 1.441(3)
C3 C10 1.497(3)
C4 C5 1.399(3)
C4 C9 1.418(3)
C5 H5 0.9300
C5 C6 1.377(3)
C6 H6 0.9300
C6 C7 1.387(3)
C7 H7 0.9300
C7 C8 1.371(3)
C8 H8 0.9300
C8 C9 1.393(3)
C11 H11A 0.9700
C11 H11B 0.9700
C11 C12 1.454(3)
C12 C13 1.155(4)
C13 H13 0.9300
C14 H14A 0.9700
C14 H14B 0.9700
C14 C15 1.464(3)
C15 C16 1.161(3)
C16 H16 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C16 H16 O2 1_554 0.93 2.34 3.214(3) 157.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139050486
