#------------------------------------------------------------------------------
#$Date: 2020-08-14 07:43:26 +0300 (Fri, 14 Aug 2020) $
#$Revision: 255313 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022230.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_2022230
loop_
_publ_author_name
'Rodríguez, Diego'
'Guerrero, Sergio Andrés'
'Palma, Alirio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 4-Styrylquinolines from cyclocondensation reactions between
 (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and
 regiochemistry
;
_journal_coeditor_code           SK3755
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620010803
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C22 H18 F3 N O2'
_chemical_formula_moiety         'C22 H18 F3 N O2'
_chemical_formula_sum            'C22 H18 F3 N O2'
_chemical_formula_weight         385.37
_chemical_name_common
;
Ethyl
(E)-2-methyl-4-[4-(trifluoromethyl)styryl]quinoline-3-carboxylate
;
_chemical_name_systematic
;Ethyl
(E)-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline-3-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                105.446(4)
_cell_angle_beta                 99.763(4)
_cell_angle_gamma                97.204(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7465(10)
_cell_length_b                   9.9436(11)
_cell_length_c                   11.1116(11)
_cell_measurement_reflns_used    4022
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.305
_cell_measurement_theta_min      2.160
_cell_volume                     903.08(17)
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            59876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_min         2.160
_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    0.111
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.9542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.427
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0439
_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)+(0.0452P)²+0.7003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                3692
_reflns_number_total             4491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3755sup1.cif
_cod_data_source_block           VI
_cod_database_code               2022230
_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   0.971
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2.014
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.07789(14) 0.22664(13) 0.15945(11) 0.0204(2) Uani d 1 . .
C C2 0.07976(16) 0.36156(15) 0.21549(13) 0.0192(3) Uani d 1 . .
C C3 0.16984(15) 0.43512(14) 0.34110(13) 0.0171(3) Uani d 1 . .
C C4 0.25843(15) 0.36523(14) 0.41074(12) 0.0168(3) Uani d 1 . .
C C4A 0.26008(15) 0.21910(14) 0.35031(13) 0.0173(3) Uani d 1 . .
C C5 0.34837(17) 0.13520(15) 0.40993(14) 0.0216(3) Uani d 1 . .
H H5 0.4093 0.1758 0.4944 0.026 Uiso calc 1 . .
C C6 0.34646(18) -0.00371(16) 0.34678(15) 0.0251(3) Uani d 1 . .
H H6 0.4067 -0.0585 0.3877 0.030 Uiso calc 1 . .
C C7 0.25608(19) -0.06624(15) 0.22177(14) 0.0250(3) Uani d 1 . .
H H7 0.2562 -0.1626 0.1789 0.030 Uiso calc 1 . .
C C8 0.16816(18) 0.01086(15) 0.16161(14) 0.0232(3) Uani d 1 . .
H H8 0.1067 -0.0323 0.0776 0.028 Uiso calc 1 . .
C C8A 0.16872(16) 0.15504(14) 0.22455(13) 0.0187(3) Uani d 1 . .
C C21 -0.01256(19) 0.43927(16) 0.13843(14) 0.0251(3) Uani d 1 . .
H H21A -0.0605 0.3749 0.0530 0.038 Uiso calc 1 . .
H H21B 0.0581 0.5199 0.1310 0.038 Uiso calc 1 . .
H H21C -0.0955 0.4737 0.1810 0.038 Uiso calc 1 . .
C C31 0.17896(16) 0.59297(14) 0.38398(13) 0.0180(3) Uani d 1 . .
O O31 0.29053(12) 0.67679(11) 0.38197(10) 0.0231(2) Uani d 1 . .
O O32 0.04628(11) 0.62833(10) 0.41672(9) 0.0200(2) Uani d 1 . .
C C32 0.03379(17) 0.77805(14) 0.44196(14) 0.0207(3) Uani d 1 . .
H H32A -0.0788 0.7871 0.4320 0.025 Uiso calc 1 . .
H H32B 0.0773 0.8161 0.3786 0.025 Uiso calc 1 . .
C C33 0.12155(18) 0.86413(16) 0.57495(14) 0.0250(3) Uani d 1 . .
H H33A 0.0848 0.8219 0.6375 0.037 Uiso calc 1 . .
H H33B 0.1019 0.9616 0.5917 0.037 Uiso calc 1 . .
H H33C 0.2348 0.8646 0.5818 0.037 Uiso calc 1 . .
C C41 0.35128(16) 0.43372(14) 0.54207(13) 0.0184(3) Uani d 1 . .
H H41 0.4482 0.4038 0.5650 0.022 Uiso calc 1 . .
C C42 0.31086(16) 0.53430(15) 0.63157(13) 0.0193(3) Uani d 1 . .
H H42 0.2140 0.5648 0.6098 0.023 Uiso calc 1 . .
C C421 0.40671(16) 0.60055(15) 0.76133(13) 0.0192(3) Uani d 1 . .
C C422 0.52605(17) 0.53948(15) 0.81430(13) 0.0213(3) Uani d 1 . .
H H422 0.5451 0.4509 0.7667 0.026 Uiso calc 1 . .
C C423 0.61718(17) 0.60661(16) 0.93570(14) 0.0236(3) Uani d 1 . .
H H423 0.6985 0.5643 0.9707 0.028 Uiso calc 1 . .
C C424 0.58945(17) 0.73547(16) 1.00582(13) 0.0228(3) Uani d 1 . .
C C425 0.46796(19) 0.79605(16) 0.95666(14) 0.0259(3) Uani d 1 . .
H H425 0.4474 0.8832 1.0059 0.031 Uiso calc 1 . .
C C426 0.37692(18) 0.72844(16) 0.83523(14) 0.0240(3) Uani d 1 . .
H H426 0.2933 0.7695 0.8018 0.029 Uiso calc 1 . .
C C427 0.6902(2) 0.81210(18) 1.13510(15) 0.0302(3) Uani d 1 . .
F F471 0.74662(16) 0.94629(12) 1.14494(11) 0.0523(3) Uani d 1 . .
F F472 0.81434(15) 0.75355(14) 1.16419(11) 0.0539(4) Uani d 1 . .
F F473 0.61164(15) 0.81641(14) 1.22927(10) 0.0506(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'
O O 0.0106 0.0060 '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(12) ?
N1 C2 C3 . . 122.90(12) ?
N1 C2 C21 . . 116.74(12) ?
C3 C2 C21 . . 120.30(12) ?
C4 C3 C2 . . 120.52(12) ?
C4 C3 C31 . . 122.57(12) ?
C2 C3 C31 . . 116.42(11) ?
C3 C4 C4A . . 117.29(12) ?
C3 C4 C41 . . 123.40(12) ?
C4A C4 C41 . . 119.30(12) ?
C5 C4A C8A . . 118.41(12) ?
C5 C4A C4 . . 123.25(12) ?
C8A C4A C4 . . 118.35(12) ?
C6 C5 C4A . . 120.57(13) ?
C6 C5 H5 . . 119.7 ?
C4A C5 H5 . . 119.7 ?
C5 C6 C7 . . 120.64(13) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C8 C7 C6 . . 120.48(13) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C8A . . 120.02(13) ?
C7 C8 H8 . . 120.0 ?
C8A C8 H8 . . 120.0 ?
N1 C8A C8 . . 117.31(12) ?
N1 C8A C4A . . 122.82(12) ?
C8 C8A C4A . . 119.87(12) ?
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 ?
O31 C31 O32 . . 124.46(13) ?
O31 C31 C3 . . 123.44(12) ?
O32 C31 C3 . . 111.98(11) ?
C31 O32 C32 . . 116.34(11) ?
O32 C32 C33 . . 111.65(11) ?
O32 C32 H32A . . 109.3 ?
C33 C32 H32A . . 109.3 ?
O32 C32 H32B . . 109.3 ?
C33 C32 H32B . . 109.3 ?
H32A C32 H32B . . 108.0 ?
C32 C33 H33A . . 109.5 ?
C32 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C32 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C42 C41 C4 . . 125.72(13) ?
C42 C41 H41 . . 117.1 ?
C4 C41 H41 . . 117.1 ?
C41 C42 C421 . . 124.22(13) ?
C41 C42 H42 . . 117.9 ?
C421 C42 H42 . . 117.9 ?
C422 C421 C426 . . 118.55(13) ?
C422 C421 C42 . . 122.19(13) ?
C426 C421 C42 . . 119.26(13) ?
C423 C422 C421 . . 120.76(13) ?
C423 C422 H422 . . 119.6 ?
C421 C422 H422 . . 119.6 ?
C424 C423 C422 . . 119.87(13) ?
C424 C423 H423 . . 120.1 ?
C422 C423 H423 . . 120.1 ?
C423 C424 C425 . . 120.37(13) ?
C423 C424 C427 . . 120.69(14) ?
C425 C424 C427 . . 118.94(14) ?
C426 C425 C424 . . 119.56(14) ?
C426 C425 H425 . . 120.2 ?
C424 C425 H425 . . 120.2 ?
C425 C426 C421 . . 120.83(14) ?
C425 C426 H426 . . 119.6 ?
C421 C426 H426 . . 119.6 ?
F472 C427 F471 . . 106.29(15) ?
F472 C427 F473 . . 105.83(14) ?
F471 C427 F473 . . 106.37(14) ?
F472 C427 C424 . . 113.19(14) ?
F471 C427 C424 . . 111.94(13) ?
F473 C427 C424 . . 112.70(14) ?
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 . 1.3168(18) ?
N1 C8A . 1.3720(18) ?
C2 C3 . 1.4292(18) ?
C2 C21 . 1.5021(19) ?
C3 C4 . 1.3786(18) ?
C3 C31 . 1.5014(18) ?
C4 C4A . 1.4322(18) ?
C4 C41 . 1.4774(18) ?
C4A C5 . 1.4191(19) ?
C4A C8A . 1.4200(18) ?
C5 C6 . 1.369(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.409(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.368(2) ?
C7 H7 . 0.9500 ?
C8 C8A . 1.4168(19) ?
C8 H8 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C31 O31 . 1.2087(17) ?
C31 O32 . 1.3342(17) ?
O32 C32 . 1.4614(16) ?
C32 C33 . 1.511(2) ?
C32 H32A . 0.9900 ?
C32 H32B . 0.9900 ?
C33 H33A . 0.9800 ?
C33 H33B . 0.9800 ?
C33 H33C . 0.9800 ?
C41 C42 . 1.3388(19) ?
C41 H41 . 0.9500 ?
C42 C421 . 1.4701(18) ?
C42 H42 . 0.9500 ?
C421 C422 . 1.3949(19) ?
C421 C426 . 1.400(2) ?
C422 C423 . 1.3867(19) ?
C422 H422 . 0.9500 ?
C423 C424 . 1.385(2) ?
C423 H423 . 0.9500 ?
C424 C425 . 1.389(2) ?
C424 C427 . 1.497(2) ?
C425 C426 . 1.387(2) ?
C425 H425 . 0.9500 ?
C426 H426 . 0.9500 ?
C427 F472 . 1.328(2) ?
C427 F471 . 1.332(2) ?
C427 F473 . 1.340(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
C41 H41 O31 2_666 0.95 2.54 3.4922(18) 178 no
C422 H422 O31 2_666 0.95 2.56 3.3924(19) 146 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 . . . . -1.0(2) ?
C8A N1 C2 C21 . . . . 176.13(12) ?
N1 C2 C3 C4 . . . . -1.0(2) ?
C21 C2 C3 C4 . . . . -178.09(13) ?
N1 C2 C3 C31 . . . . 171.16(13) ?
C21 C2 C3 C31 . . . . -5.91(19) ?
C2 C3 C4 C4A . . . . 2.11(19) ?
C31 C3 C4 C4A . . . . -169.59(12) ?
C2 C3 C4 C41 . . . . -178.53(12) ?
C31 C3 C4 C41 . . . . 9.8(2) ?
C3 C4 C4A C5 . . . . 178.82(13) ?
C41 C4 C4A C5 . . . . -0.6(2) ?
C3 C4 C4A C8A . . . . -1.24(19) ?
C41 C4 C4A C8A . . . . 179.38(12) ?
C8A C4A C5 C6 . . . . 0.7(2) ?
C4 C4A C5 C6 . . . . -179.36(13) ?
C4A C5 C6 C7 . . . . -0.4(2) ?
C5 C6 C7 C8 . . . . -0.3(2) ?
C6 C7 C8 C8A . . . . 0.6(2) ?
C2 N1 C8A C8 . . . . -178.55(13) ?
C2 N1 C8A C4A . . . . 1.9(2) ?
C7 C8 C8A N1 . . . . -179.83(14) ?
C7 C8 C8A C4A . . . . -0.3(2) ?
C5 C4A C8A N1 . . . . 179.16(13) ?
C4 C4A C8A N1 . . . . -0.8(2) ?
C5 C4A C8A C8 . . . . -0.3(2) ?
C4 C4A C8A C8 . . . . 179.70(12) ?
C4 C3 C31 O31 . . . . 72.26(19) ?
C2 C3 C31 O31 . . . . -99.75(16) ?
C4 C3 C31 O32 . . . . -111.53(14) ?
C2 C3 C31 O32 . . . . 76.46(15) ?
O31 C31 O32 C32 . . . . 4.82(19) ?
C3 C31 O32 C32 . . . . -171.35(11) ?
C31 O32 C32 C33 . . . . -80.77(15) ?
C3 C4 C41 C42 . . . . 34.8(2) ?
C4A C4 C41 C42 . . . . -145.85(14) ?
C4 C41 C42 C421 . . . . -179.75(12) ?
C41 C42 C421 C422 . . . . -17.7(2) ?
C41 C42 C421 C426 . . . . 162.95(14) ?
C426 C421 C422 C423 . . . . -2.4(2) ?
C42 C421 C422 C423 . . . . 178.24(13) ?
C421 C422 C423 C424 . . . . 0.3(2) ?
C422 C423 C424 C425 . . . . 1.8(2) ?
C422 C423 C424 C427 . . . . -177.82(14) ?
C423 C424 C425 C426 . . . . -1.7(2) ?
C427 C424 C425 C426 . . . . 177.92(14) ?
C424 C425 C426 C421 . . . . -0.5(2) ?
C422 C421 C426 C425 . . . . 2.5(2) ?
C42 C421 C426 C425 . . . . -178.13(14) ?
C423 C424 C427 F472 . . . . 8.1(2) ?
C425 C424 C427 F472 . . . . -171.53(15) ?
C423 C424 C427 F471 . . . . 128.18(17) ?
C425 C424 C427 F471 . . . . -51.4(2) ?
C423 C424 C427 F473 . . . . -111.97(17) ?
C425 C424 C427 F473 . . . . 68.4(2) ?

_cod_database_fobs_code 2022230
