#------------------------------------------------------------------------------
#$Date: 2022-09-13 04:49:45 +0300 (Tue, 13 Sep 2022) $
#$Revision: 277788 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022667.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_2022667
loop_
_publ_author_name
'Vera, Diana Rocío'
'Mantilla, Juan P.'
'Palma, Alirio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Synthesis and spectroscopic and structural characterization of three new
 2-methyl-4-styrylquinolines formed using Friedländer reactions between
 (2-aminophenyl)chalcones and acetone
;
_journal_coeditor_code           KY3221
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622008634
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C18 H14 F N'
_chemical_formula_moiety         'C18 H14 F N'
_chemical_formula_sum            'C18 H14 F N'
_chemical_formula_weight         263.30
_chemical_name_common
;
(E)-4-(4-Fluorostyryl)-2-methylquinoline
;
_chemical_name_systematic
;
(E)-4-[2-(4-Fluorophenyl)ethenyl]-2-methylquinoline
;
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 103.133(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5921(7)
_cell_length_b                   12.7103(6)
_cell_length_c                   7.6215(3)
_cell_measurement_reflns_used    2950
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.509
_cell_measurement_theta_min      2.221
_cell_volume                     1282.25(10)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38068
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.221
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0417
_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)+(0.0315P)²+0.8512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                2342
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ky3221sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022667
_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.
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.38298(9) 0.09596(10) 0.33198(16) 0.0184(3) Uani d 1 . .
C C2 0.29100(11) 0.11467(12) 0.23444(19) 0.0176(3) Uani d 1 . .
C C3 0.25558(11) 0.21776(12) 0.18306(19) 0.0176(3) Uani d 1 . .
H H3 0.1892 0.2272 0.1115 0.021 Uiso calc 1 . .
C C4 0.31611(11) 0.30404(11) 0.23560(19) 0.0167(3) Uani d 1 . .
C C4A 0.41653(10) 0.28596(11) 0.33921(19) 0.0163(3) Uani d 1 . .
C C5 0.48647(11) 0.36772(12) 0.4033(2) 0.0191(3) Uani d 1 . .
H H5 0.4685 0.4386 0.3719 0.023 Uiso calc 1 . .
C C6 0.57984(11) 0.34538(12) 0.5101(2) 0.0204(3) Uani d 1 . .
H H6 0.6260 0.4008 0.5523 0.024 Uiso calc 1 . .
C C7 0.60735(11) 0.24060(12) 0.5574(2) 0.0204(3) Uani d 1 . .
H H7 0.6716 0.2261 0.6336 0.024 Uiso calc 1 . .
C C8 0.54267(11) 0.15932(12) 0.4950(2) 0.0196(3) Uani d 1 . .
H H8 0.5628 0.0889 0.5257 0.024 Uiso calc 1 . .
C C8A 0.44577(11) 0.18016(11) 0.38490(19) 0.0170(3) Uani d 1 . .
C C21 0.22304(12) 0.02127(12) 0.1834(2) 0.0225(3) Uani d 1 . .
H H21A 0.1914 0.0036 0.2830 0.034 Uiso calc 1 . .
H H21B 0.2628 -0.0388 0.1578 0.034 Uiso calc 1 . .
H H21C 0.1705 0.0381 0.0759 0.034 Uiso calc 1 . .
C C41 0.27793(11) 0.41183(11) 0.19305(19) 0.0174(3) Uani d 1 . .
H H41 0.3216 0.4626 0.1597 0.021 Uiso calc 1 . .
C C42 0.18432(11) 0.44098(11) 0.19947(19) 0.0173(3) Uani d 1 . .
H H42 0.1420 0.3877 0.2295 0.021 Uiso calc 1 . .
C C421 0.13959(10) 0.54644(11) 0.16520(18) 0.0163(3) Uani d 1 . .
C C422 0.04269(11) 0.56378(12) 0.1940(2) 0.0191(3) Uani d 1 . .
H H422 0.0077 0.5074 0.2345 0.023 Uiso calc 1 . .
C C423 -0.00317(11) 0.66179(12) 0.1644(2) 0.0199(3) Uani d 1 . .
H H423 -0.0691 0.6729 0.1835 0.024 Uiso calc 1 . .
C C424 0.04914(11) 0.74221(11) 0.10693(19) 0.0187(3) Uani d 1 . .
F F424 0.00528(7) 0.83934(7) 0.08198(12) 0.0255(2) Uani d 1 . .
C C425 0.14458(11) 0.72940(12) 0.0748(2) 0.0192(3) Uani d 1 . .
H H425 0.1785 0.7863 0.0333 0.023 Uiso calc 1 . .
C C426 0.18939(11) 0.63090(12) 0.10502(19) 0.0181(3) Uani d 1 . .
H H426 0.2551 0.6206 0.0845 0.022 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C8A . . 118.08(13) ?
N1 C2 C3 . . 122.60(13) ?
N1 C2 C21 . . 116.82(13) ?
C3 C2 C21 . . 120.56(13) ?
C4 C3 C2 . . 120.85(13) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C4A . . 117.71(13) ?
C3 C4 C41 . . 121.31(13) ?
C4A C4 C41 . . 120.94(13) ?
C5 C4A C8A . . 118.70(13) ?
C5 C4A C4 . . 123.56(13) ?
C8A C4A C4 . . 117.71(13) ?
C6 C5 C4A . . 120.64(14) ?
C6 C5 H5 . . 119.7 ?
C4A C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.23(14) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C6 . . 120.82(14) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C8A . . 120.11(14) ?
C7 C8 H8 . . 119.9 ?
C8A C8 H8 . . 119.9 ?
N1 C8A C8 . . 117.46(13) ?
N1 C8A C4A . . 123.03(13) ?
C8 C8A C4A . . 119.48(13) ?
C2 C21 H21A . . 109.5 ?
C2 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C2 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C42 C41 C4 . . 122.66(14) ?
C42 C41 H41 . . 118.7 ?
C4 C41 H41 . . 118.7 ?
C41 C42 C421 . . 127.21(14) ?
C41 C42 H42 . . 116.4 ?
C421 C42 H42 . . 116.4 ?
C426 C421 C422 . . 118.18(13) ?
C426 C421 C42 . . 123.07(13) ?
C422 C421 C42 . . 118.76(13) ?
C423 C422 C421 . . 121.28(14) ?
C423 C422 H422 . . 119.4 ?
C421 C422 H422 . . 119.4 ?
C424 C423 C422 . . 118.29(13) ?
C424 C423 H423 . . 120.9 ?
C422 C423 H423 . . 120.9 ?
F424 C424 C423 . . 118.45(13) ?
F424 C424 C425 . . 118.63(13) ?
C423 C424 C425 . . 122.92(14) ?
C424 C425 C426 . . 118.07(14) ?
C424 C425 H425 . . 121.0 ?
C426 C425 H425 . . 121.0 ?
C425 C426 C421 . . 121.26(13) ?
C425 C426 H426 . . 119.4 ?
C421 C426 H426 . . 119.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3227(19) ?
N1 C8A . 1.3712(19) ?
C2 C3 . 1.420(2) ?
C2 C21 . 1.500(2) ?
C3 C4 . 1.375(2) ?
C3 H3 . 0.9500 ?
C4 C4A . 1.432(2) ?
C4 C41 . 1.475(2) ?
C4A C5 . 1.418(2) ?
C4A C8A . 1.423(2) ?
C5 C6 . 1.373(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.408(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.370(2) ?
C7 H7 . 0.9500 ?
C8 C8A . 1.417(2) ?
C8 H8 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C41 C42 . 1.337(2) ?
C41 H41 . 0.9500 ?
C42 C421 . 1.471(2) ?
C42 H42 . 0.9500 ?
C421 C426 . 1.401(2) ?
C421 C422 . 1.401(2) ?
C422 C423 . 1.388(2) ?
C422 H422 . 0.9500 ?
C423 C424 . 1.373(2) ?
C423 H423 . 0.9500 ?
C424 F424 . 1.3653(16) ?
C424 C425 . 1.383(2) ?
C425 C426 . 1.388(2) ?
C425 H425 . 0.9500 ?
C426 H426 . 0.9500 ?
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
_geom_hbond_publ_flag
C8 H8 N1 3_656 0.95 2.62 3.561(2) 170 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A N1 C2 C3 . . . . 0.1(2) ?
C8A N1 C2 C21 . . . . -178.20(13) ?
N1 C2 C3 C4 . . . . -0.9(2) ?
C21 C2 C3 C4 . . . . 177.35(13) ?
C2 C3 C4 C4A . . . . 1.7(2) ?
C2 C3 C4 C41 . . . . -175.99(13) ?
C3 C4 C4A C5 . . . . -179.48(13) ?
C41 C4 C4A C5 . . . . -1.8(2) ?
C3 C4 C4A C8A . . . . -1.72(19) ?
C41 C4 C4A C8A . . . . 175.96(13) ?
C8A C4A C5 C6 . . . . -1.2(2) ?
C4 C4A C5 C6 . . . . 176.49(14) ?
C4A C5 C6 C7 . . . . 0.0(2) ?
C5 C6 C7 C8 . . . . 1.4(2) ?
C6 C7 C8 C8A . . . . -1.5(2) ?
C2 N1 C8A C8 . . . . 177.65(13) ?
C2 N1 C8A C4A . . . . -0.2(2) ?
C7 C8 C8A N1 . . . . -177.65(13) ?
C7 C8 C8A C4A . . . . 0.3(2) ?
C5 C4A C8A N1 . . . . 178.89(13) ?
C4 C4A C8A N1 . . . . 1.0(2) ?
C5 C4A C8A C8 . . . . 1.1(2) ?
C4 C4A C8A C8 . . . . -176.78(13) ?
C3 C4 C41 C42 . . . . 38.8(2) ?
C4A C4 C41 C42 . . . . -138.76(15) ?
C4 C41 C42 C421 . . . . 178.04(14) ?
C41 C42 C421 C426 . . . . 5.5(2) ?
C41 C42 C421 C422 . . . . -174.47(15) ?
C426 C421 C422 C423 . . . . -0.2(2) ?
C42 C421 C422 C423 . . . . 179.79(14) ?
C421 C422 C423 C424 . . . . -0.4(2) ?
C422 C423 C424 F424 . . . . -178.42(13) ?
C422 C423 C424 C425 . . . . 1.0(2) ?
F424 C424 C425 C426 . . . . 178.42(13) ?
C423 C424 C425 C426 . . . . -1.0(2) ?
C424 C425 C426 C421 . . . . 0.4(2) ?
C422 C421 C426 C425 . . . . 0.2(2) ?
C42 C421 C426 C425 . . . . -179.79(14) ?

_cod_database_fobs_code 2022667
