#------------------------------------------------------------------------------
#$Date: 2022-09-13 04:49:45 +0300 (Tue, 13 Sep 2022) $
#$Revision: 277788 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022668.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_2022668
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          'C19 H14 F3 N'
_chemical_formula_moiety         'C19 H14 F3 N'
_chemical_formula_sum            'C19 H14 F3 N'
_chemical_formula_weight         313.31
_chemical_name_common
;
(E)-2-Methyl-4-[4-(trifluoromethyl)styryl]quinoline
;
_chemical_name_systematic
;
(E)-2-Methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.440(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2696(10)
_cell_length_b                   10.8096(7)
_cell_length_c                   16.1495(8)
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.295
_cell_measurement_theta_min      2.223
_cell_volume                     3013.8(3)
_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  0.0850
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            46287
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         2.223
_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    0.107
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0474
_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)+(0.0491P)²+3.9260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2921
_reflns_number_total             3750
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ky3221sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022668
_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   0.983
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.35530(8) 0.65666(13) 0.70993(8) 0.0214(3) Uani d 1 . .
C C2 0.40811(9) 0.73252(15) 0.68089(10) 0.0220(3) Uani d 1 . .
C C3 0.47497(9) 0.69044(15) 0.64043(10) 0.0208(3) Uani d 1 . .
H H3 0.5106 0.7490 0.6197 0.025 Uiso calc 1 . .
C C4 0.48905(9) 0.56618(15) 0.63077(9) 0.0184(3) Uani d 1 . .
C C4A 0.43320(9) 0.48166(15) 0.66242(9) 0.0176(3) Uani d 1 . .
C C5 0.44046(9) 0.35106(15) 0.65886(10) 0.0216(3) Uani d 1 . .
H H5 0.4847 0.3153 0.6345 0.026 Uiso calc 1 . .
C C6 0.38443(10) 0.27589(16) 0.69007(10) 0.0242(3) Uani d 1 . .
H H6 0.3905 0.1886 0.6874 0.029 Uiso calc 1 . .
C C7 0.31786(10) 0.32625(16) 0.72612(10) 0.0245(4) Uani d 1 . .
H H7 0.2789 0.2732 0.7465 0.029 Uiso calc 1 . .
C C8 0.30976(9) 0.45181(16) 0.73152(10) 0.0221(3) Uani d 1 . .
H H8 0.2651 0.4855 0.7562 0.026 Uiso calc 1 . .
C C8A 0.36711(9) 0.53235(15) 0.70072(9) 0.0187(3) Uani d 1 . .
C C21 0.39360(11) 0.86894(16) 0.69174(13) 0.0324(4) Uani d 1 . .
H H21A 0.3714 0.8837 0.7461 0.049 Uiso calc 1 . .
H H21B 0.3574 0.8978 0.6482 0.049 Uiso calc 1 . .
H H21C 0.4426 0.9141 0.6879 0.049 Uiso calc 1 . .
C C41 0.55777(9) 0.52090(15) 0.58805(9) 0.0189(3) Uani d 1 . .
H H41 0.5541 0.4430 0.5610 0.023 Uiso calc 1 . .
C C42 0.62479(9) 0.58178(15) 0.58464(10) 0.0205(3) Uani d 1 . .
H H42 0.6276 0.6595 0.6120 0.025 Uiso calc 1 . .
C C421 0.69464(9) 0.54044(15) 0.54269(9) 0.0181(3) Uani d 1 . .
C C422 0.76181(9) 0.61241(16) 0.55017(10) 0.0224(3) Uani d 1 . .
H H422 0.7611 0.6860 0.5824 0.027 Uiso calc 1 . .
C C423 0.82949(9) 0.57845(15) 0.51149(10) 0.0229(3) Uani d 1 . .
H H423 0.8747 0.6282 0.5172 0.027 Uiso calc 1 . .
C C424 0.83043(9) 0.47101(15) 0.46437(9) 0.0188(3) Uani d 1 . .
C C425 0.76429(9) 0.39804(15) 0.45619(9) 0.0196(3) Uani d 1 . .
H H425 0.7652 0.3246 0.4239 0.024 Uiso calc 1 . .
C C426 0.69721(9) 0.43241(15) 0.49513(10) 0.0198(3) Uani d 1 . .
H H426 0.6523 0.3820 0.4895 0.024 Uiso calc 1 . .
C C427 0.90242(9) 0.43013(16) 0.42322(10) 0.0232(3) Uani d 1 . .
F F471 0.93775(6) 0.33641(11) 0.46404(8) 0.0390(3) Uani d 1 . .
F F472 0.88912(7) 0.38927(13) 0.34613(7) 0.0460(3) Uani d 1 . .
F F473 0.95562(6) 0.51919(11) 0.41781(8) 0.0390(3) Uani d 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 . . 117.72(14) ?
N1 C2 C3 . . 122.85(15) ?
N1 C2 C21 . . 116.62(14) ?
C3 C2 C21 . . 120.53(15) ?
C4 C3 C2 . . 120.99(15) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C4A . . 117.40(14) ?
C3 C4 C41 . . 121.69(14) ?
C4A C4 C41 . . 120.90(14) ?
C5 C4A C8A . . 118.29(14) ?
C5 C4A C4 . . 124.02(14) ?
C8A C4A C4 . . 117.69(14) ?
C6 C5 C4A . . 120.77(15) ?
C6 C5 H5 . . 119.6 ?
C4A C5 H5 . . 119.6 ?
C5 C6 C7 . . 120.90(16) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 119.67(15) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C8A . . 120.89(15) ?
C7 C8 H8 . . 119.6 ?
C8A C8 H8 . . 119.6 ?
N1 C8A C8 . . 117.23(14) ?
N1 C8A C4A . . 123.33(14) ?
C8 C8A C4A . . 119.44(15) ?
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 . . 124.49(15) ?
C42 C41 H41 . . 117.8 ?
C4 C41 H41 . . 117.8 ?
C41 C42 C421 . . 126.36(15) ?
C41 C42 H42 . . 116.8 ?
C421 C42 H42 . . 116.8 ?
C426 C421 C422 . . 118.27(14) ?
C426 C421 C42 . . 123.05(14) ?
C422 C421 C42 . . 118.68(14) ?
C423 C422 C421 . . 121.30(15) ?
C423 C422 H422 . . 119.4 ?
C421 C422 H422 . . 119.4 ?
C422 C423 C424 . . 119.29(15) ?
C422 C423 H423 . . 120.4 ?
C424 C423 H423 . . 120.4 ?
C423 C424 C425 . . 120.34(14) ?
C423 C424 C427 . . 120.88(14) ?
C425 C424 C427 . . 118.77(14) ?
C426 C425 C424 . . 119.97(15) ?
C426 C425 H425 . . 120.0 ?
C424 C425 H425 . . 120.0 ?
C425 C426 C421 . . 120.83(14) ?
C425 C426 H426 . . 119.6 ?
C421 C426 H426 . . 119.6 ?
F473 C427 F472 . . 106.26(14) ?
F473 C427 F471 . . 105.69(14) ?
F472 C427 F471 . . 105.82(14) ?
F473 C427 C424 . . 113.47(14) ?
F472 C427 C424 . . 112.81(14) ?
F471 C427 C424 . . 112.17(13) ?
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 . 1.321(2) ?
N1 C8A . 1.368(2) ?
C2 C3 . 1.416(2) ?
C2 C21 . 1.507(2) ?
C3 C4 . 1.375(2) ?
C3 H3 . 0.9500 ?
C4 C4A . 1.432(2) ?
C4 C41 . 1.471(2) ?
C4A C5 . 1.419(2) ?
C4A C8A . 1.422(2) ?
C5 C6 . 1.369(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.411(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.368(2) ?
C7 H7 . 0.9500 ?
C8 C8A . 1.418(2) ?
C8 H8 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C41 C42 . 1.334(2) ?
C41 H41 . 0.9500 ?
C42 C421 . 1.468(2) ?
C42 H42 . 0.9500 ?
C421 C426 . 1.399(2) ?
C421 C422 . 1.400(2) ?
C422 C423 . 1.388(2) ?
C422 H422 . 0.9500 ?
C423 C424 . 1.389(2) ?
C423 H423 . 0.9500 ?
C424 C425 . 1.392(2) ?
C424 C427 . 1.491(2) ?
C425 C426 . 1.383(2) ?
C425 H425 . 0.9500 ?
C426 H426 . 0.9500 ?
C427 F473 . 1.3350(19) ?
C427 F472 . 1.335(2) ?
C427 F471 . 1.347(2) ?
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
C426 H426 Cg1 5_666 0.95 2.86 3.3627(17) 114 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 . . . . 0.7(2) ?
C8A N1 C2 C21 . . . . 179.91(15) ?
N1 C2 C3 C4 . . . . -1.3(3) ?
C21 C2 C3 C4 . . . . 179.50(16) ?
C2 C3 C4 C4A . . . . 0.6(2) ?
C2 C3 C4 C41 . . . . 179.28(15) ?
C3 C4 C4A C5 . . . . -178.50(15) ?
C41 C4 C4A C5 . . . . 2.8(2) ?
C3 C4 C4A C8A . . . . 0.6(2) ?
C41 C4 C4A C8A . . . . -178.12(13) ?
C8A C4A C5 C6 . . . . 1.3(2) ?
C4 C4A C5 C6 . . . . -179.65(15) ?
C4A C5 C6 C7 . . . . 0.4(2) ?
C5 C6 C7 C8 . . . . -1.3(3) ?
C6 C7 C8 C8A . . . . 0.5(2) ?
C2 N1 C8A C8 . . . . -179.51(14) ?
C2 N1 C8A C4A . . . . 0.6(2) ?
C7 C8 C8A N1 . . . . -178.81(15) ?
C7 C8 C8A C4A . . . . 1.1(2) ?
C5 C4A C8A N1 . . . . 177.91(14) ?
C4 C4A C8A N1 . . . . -1.2(2) ?
C5 C4A C8A C8 . . . . -2.0(2) ?
C4 C4A C8A C8 . . . . 178.87(14) ?
C3 C4 C41 C42 . . . . 28.1(2) ?
C4A C4 C41 C42 . . . . -153.27(16) ?
C4 C41 C42 C421 . . . . -179.85(15) ?
C41 C42 C421 C426 . . . . 4.6(3) ?
C41 C42 C421 C422 . . . . -175.68(16) ?
C426 C421 C422 C423 . . . . 0.2(2) ?
C42 C421 C422 C423 . . . . -179.59(15) ?
C421 C422 C423 C424 . . . . 0.1(3) ?
C422 C423 C424 C425 . . . . -0.2(2) ?
C422 C423 C424 C427 . . . . -178.80(15) ?
C423 C424 C425 C426 . . . . 0.0(2) ?
C427 C424 C425 C426 . . . . 178.65(15) ?
C424 C425 C426 C421 . . . . 0.3(2) ?
C422 C421 C426 C425 . . . . -0.3(2) ?
C42 C421 C426 C425 . . . . 179.40(15) ?
C423 C424 C427 F473 . . . . -16.7(2) ?
C425 C424 C427 F473 . . . . 164.64(15) ?
C423 C424 C427 F472 . . . . -137.61(16) ?
C425 C424 C427 F472 . . . . 43.7(2) ?
C423 C424 C427 F471 . . . . 102.99(18) ?
C425 C424 C427 F471 . . . . -75.67(19) ?

_cod_database_fobs_code 2022668
