#------------------------------------------------------------------------------
#$Date: 2021-08-19 04:42:48 +0300 (Thu, 19 Aug 2021) $
#$Revision: 268133 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022416.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_2022416
loop_
_publ_author_name
'Wolińska, Ewa'
'Wysocki, Waldemar'
'Branowska, Danuta'
'Karczmarzyk, Zbigniew'
_publ_section_title
;
 Synthesis and structures of three new pyridine-containing oxazoline
 ligands of complexes for asymmetric catalysis
;
_journal_coeditor_code           WV3005
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229621008202
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_iupac          'C21 H16 F3 N3 O'
_chemical_formula_moiety         'C21 H16 F3 N3 O'
_chemical_formula_sum            'C21 H16 F3 N3 O'
_chemical_formula_weight         383.37
_chemical_name_systematic
2-({2-[(4S)-4-Phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino)-5-(trifluoromethyl)pyridine
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   17.1109(4)
_cell_length_b                   17.1109(4)
_cell_length_c                   5.4205(2)
_cell_measurement_reflns_used    5131
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.8990
_cell_measurement_theta_min      5.1560
_cell_volume                     1374.41(7)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1994)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            18179
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.498
_diffrn_reflns_theta_min         5.170
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       prism
_exptl_crystal_F_000             594
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.125
_refine_ls_abs_structure_details
;
Flack x determined using 860 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0413
_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)+(0.0749P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2316
_reflns_number_total             3142
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wv3005sup1.cif
_cod_data_source_block           5a
_cod_original_cell_volume        1374.41(8)
_cod_database_code               2022416
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
F F8A 0.5453(8) 0.2941(7) 0.302(3) 0.134(5) Uani d 0.58(3) A 1
F F9A 0.5537(8) 0.3453(14) 0.6626(16) 0.161(5) Uani d 0.58(3) A 1
F F10A 0.5801(8) 0.4288(6) 0.349(4) 0.157(5) Uani d 0.58(3) A 1
F F8B 0.5479(13) 0.325(2) 0.220(4) 0.198(11) Uani d 0.42(3) A 2
F F9B 0.5284(15) 0.294(2) 0.606(5) 0.207(10) Uani d 0.42(3) A 2
F F10B 0.5777(11) 0.4298(9) 0.475(5) 0.176(10) Uani d 0.42(3) A 2
O O19 -0.06559(17) 0.2915(2) 0.3839(7) 0.1013(9) Uani d 1 . .
N N1 0.2874(2) 0.2546(2) 0.2033(6) 0.0806(8) Uani d 1 . .
N N11 0.1675(2) 0.2696(2) 0.3617(6) 0.0820(9) Uani d 1 . .
H H11 0.151(4) 0.295(4) 0.480(11) 0.123 Uiso d 1 . .
N N22 0.0686(2) 0.3349(2) 0.5615(7) 0.0878(9) Uani d 1 . .
C C2 0.2543(2) 0.2843(2) 0.3777(7) 0.0732(9) Uani d 1 . .
C C3 0.3048(3) 0.3323(3) 0.5854(8) 0.0844(10) Uani d 1 . .
H H3 0.2791 0.3502 0.7080 0.127 Uiso calc 1 . .
C C4 0.3923(3) 0.3520(3) 0.6032(9) 0.0897(11) Uani d 1 . .
H H4 0.4278 0.3852 0.7360 0.135 Uiso calc 1 . .
C C5 0.4279(3) 0.3218(2) 0.4206(9) 0.0842(10) Uani d 1 . .
C C6 0.3728(3) 0.2737(3) 0.2297(8) 0.0858(11) Uani d 1 . .
H H6 0.3964 0.2526 0.1092 0.129 Uiso calc 1 . .
C C7 0.5231(4) 0.3447(3) 0.4322(11) 0.1130(17) Uani d 1 . .
C C12 0.0994(2) 0.2227(2) 0.1914(7) 0.0750(9) Uani d 1 . .
C C13 0.0197(2) 0.2284(2) 0.2132(8) 0.0782(9) Uani d 1 . .
C C14 -0.0514(3) 0.1797(3) 0.0512(9) 0.0929(12) Uani d 1 . .
H H14 -0.1043 0.1818 0.0689 0.139 Uiso calc 1 . .
C C15 -0.0451(3) 0.1283(3) -0.1354(11) 0.1024(13) Uani d 1 . .
H H15 -0.0927 0.0971 -0.2448 0.154 Uiso calc 1 . .
C C16 0.0327(3) 0.1240(3) -0.1568(10) 0.0956(12) Uani d 1 . .
H H16 0.0375 0.0898 -0.2829 0.143 Uiso calc 1 . .
C C17 0.1034(3) 0.1690(3) 0.0034(8) 0.0846(10) Uani d 1 . .
H H17 0.1547 0.1637 -0.0135 0.127 Uiso calc 1 . .
C C18 0.0111(2) 0.2865(3) 0.3978(8) 0.0820(11) Uani d 1 . .
C C20 -0.0607(3) 0.3492(4) 0.5869(12) 0.1141(17) Uani d 1 . .
H H201 -0.1051 0.3146 0.7124 0.171 Uiso calc 1 . .
H H202 -0.0710 0.3970 0.5291 0.171 Uiso calc 1 . .
C C21 0.0347(3) 0.3881(3) 0.6883(9) 0.0901(11) Uani d 1 . .
H H21 0.0316 0.3763 0.8659 0.135 Uiso calc 1 . .
C C23 0.0953(2) 0.4881(3) 0.6432(7) 0.0765(9) Uani d 1 . .
C C24 0.1515(3) 0.5212(3) 0.4420(8) 0.0909(11) Uani d 1 . .
H H24 0.1523 0.4810 0.3280 0.136 Uiso calc 1 . .
C C25 0.2063(3) 0.6119(3) 0.4053(10) 0.0996(13) Uani d 1 . .
H H25 0.2439 0.6326 0.2680 0.149 Uiso calc 1 . .
C C26 0.2060(3) 0.6724(3) 0.5703(11) 0.0994(13) Uani d 1 . .
H H26 0.2434 0.7341 0.5463 0.149 Uiso calc 1 . .
C C27 0.1503(3) 0.6413(3) 0.7697(10) 0.1011(14) Uani d 1 . .
H H27 0.1497 0.6821 0.8819 0.152 Uiso calc 1 . .
C C28 0.0946(3) 0.5497(3) 0.8076(9) 0.0905(11) Uani d 1 . .
H H28 0.0564 0.5294 0.9439 0.136 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'
F F 0.0727 0.0534 '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
C18 O19 C20 . . 105.8(3) ?
C2 N1 C6 . . 117.1(3) ?
C2 N11 C12 . . 131.6(4) ?
C2 N11 H11 . . 116(4) ?
C12 N11 H11 . . 113(4) ?
C18 N22 C21 . . 108.2(3) ?
N1 C2 N11 . . 120.8(3) ?
N1 C2 C3 . . 122.6(3) ?
N11 C2 C3 . . 116.6(3) ?
C4 C3 C2 . . 118.6(4) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 119.3(4) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C6 C5 C4 . . 117.7(4) ?
C6 C5 C7 . . 122.1(4) ?
C4 C5 C7 . . 120.1(4) ?
N1 C6 C5 . . 124.7(4) ?
N1 C6 H6 . . 117.6 ?
C5 C6 H6 . . 117.6 ?
F10B C7 F9B . . 111.3(11) ?
F10B C7 F8B . . 107.3(10) ?
F9B C7 F8B . . 108.5(10) ?
F8A C7 F10A . . 103.4(8) ?
F8A C7 F9A . . 105.1(8) ?
F10A C7 F9A . . 103.2(8) ?
F10B C7 C5 . . 112.8(9) ?
F9B C7 C5 . . 106.6(9) ?
F8A C7 C5 . . 116.6(6) ?
F8B C7 C5 . . 110.3(10) ?
F10A C7 C5 . . 112.6(6) ?
F9A C7 C5 . . 114.5(7) ?
N11 C12 C17 . . 124.4(3) ?
N11 C12 C13 . . 117.6(4) ?
C17 C12 C13 . . 118.0(4) ?
C14 C13 C12 . . 119.3(4) ?
C14 C13 C18 . . 118.9(3) ?
C12 C13 C18 . . 121.8(4) ?
C15 C14 C13 . . 121.5(4) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C16 C15 C14 . . 118.8(5) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C17 C16 C15 . . 121.6(5) ?
C17 C16 H16 . . 119.2 ?
C15 C16 H16 . . 119.2 ?
C16 C17 C12 . . 120.8(4) ?
C16 C17 H17 . . 119.6 ?
C12 C17 H17 . . 119.6 ?
N22 C18 O19 . . 116.9(4) ?
N22 C18 C13 . . 127.5(3) ?
O19 C18 C13 . . 115.5(4) ?
O19 C20 C21 . . 104.8(3) ?
O19 C20 H201 . . 110.8 ?
C21 C20 H201 . . 110.8 ?
O19 C20 H202 . . 110.8 ?
C21 C20 H202 . . 110.8 ?
H201 C20 H202 . . 108.9 ?
N22 C21 C23 . . 111.4(3) ?
N22 C21 C20 . . 103.2(4) ?
C23 C21 C20 . . 114.5(4) ?
N22 C21 H21 . . 109.2 ?
C23 C21 H21 . . 109.2 ?
C20 C21 H21 . . 109.2 ?
C24 C23 C28 . . 117.8(4) ?
C24 C23 C21 . . 122.5(4) ?
C28 C23 C21 . . 119.7(4) ?
C25 C24 C23 . . 121.6(4) ?
C25 C24 H24 . . 119.2 ?
C23 C24 H24 . . 119.2 ?
C24 C25 C26 . . 120.2(5) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C27 C26 C25 . . 119.3(4) ?
C27 C26 H26 . . 120.3 ?
C25 C26 H26 . . 120.3 ?
C26 C27 C28 . . 120.8(5) ?
C26 C27 H27 . . 119.6 ?
C28 C27 H27 . . 119.6 ?
C27 C28 C23 . . 120.2(4) ?
C27 C28 H28 . . 119.9 ?
C23 C28 H28 . . 119.9 ?
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
F8A C7 . 1.312(9) ?
F9A C7 . 1.352(9) ?
F10A C7 . 1.349(9) ?
F8B C7 . 1.329(11) ?
F9B C7 . 1.313(11) ?
F10B C7 . 1.298(11) ?
O19 C18 . 1.360(5) ?
O19 C20 . 1.453(6) ?
N1 C2 . 1.326(5) ?
N1 C6 . 1.336(5) ?
N11 C2 . 1.379(5) ?
N11 C12 . 1.385(5) ?
N11 H11 . 0.90(6) ?
N22 C18 . 1.275(5) ?
N22 C21 . 1.472(5) ?
C2 C3 . 1.407(6) ?
C3 C4 . 1.364(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.390(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.364(6) ?
C5 C7 . 1.473(7) ?
C6 H6 . 0.9300 ?
C12 C17 . 1.396(6) ?
C12 C13 . 1.421(5) ?
C13 C14 . 1.389(6) ?
C13 C18 . 1.469(6) ?
C14 C15 . 1.379(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.374(7) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.371(6) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C20 C21 . 1.524(7) ?
C20 H201 . 0.9700 ?
C20 H202 . 0.9700 ?
C21 C23 . 1.512(6) ?
C21 H21 . 0.9800 ?
C23 C24 . 1.375(6) ?
C23 C28 . 1.386(6) ?
C24 C25 . 1.369(7) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.370(7) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.361(7) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.383(6) ?
C27 H27 . 0.9300 ?
C28 H28 . 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
_geom_hbond_publ_flag
N11 H11 N22 . 0.90(7) 1.90(7) 2.681(5) 144(6) y
C14 H14 O19 . 0.93 2.37 2.727(6) 102 y
C17 H17 N1 . 0.93 2.33 2.936(6) 123 y
C24 H24 N22 . 0.93 2.51 2.841(5) 101 y
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
C6 N1 C2 N11 . . . . 178.3(3) ?
C6 N1 C2 C3 . . . . -1.2(5) ?
C12 N11 C2 N1 . . . . 3.5(6) ?
C12 N11 C2 C3 . . . . -177.0(4) ?
N1 C2 C3 C4 . . . . 2.5(6) ?
N11 C2 C3 C4 . . . . -177.0(3) ?
C2 C3 C4 C5 . . . . -2.0(6) ?
C3 C4 C5 C6 . . . . 0.3(6) ?
C3 C4 C5 C7 . . . . 178.1(4) ?
C2 N1 C6 C5 . . . . -0.7(6) ?
C4 C5 C6 N1 . . . . 1.1(6) ?
C7 C5 C6 N1 . . . . -176.6(4) ?
C6 C5 C7 F10B . . . . 129.7(15) ?
C4 C5 C7 F10B . . . . -48.0(16) ?
C6 C5 C7 F9B . . . . -107.8(18) ?
C4 C5 C7 F9B . . . . 74.5(18) ?
C6 C5 C7 F8A . . . . -21.9(10) ?
C4 C5 C7 F8A . . . . 160.4(9) ?
C6 C5 C7 F8B . . . . 9.8(18) ?
C4 C5 C7 F8B . . . . -167.9(17) ?
C6 C5 C7 F10A . . . . 97.3(12) ?
C4 C5 C7 F10A . . . . -80.4(12) ?
C6 C5 C7 F9A . . . . -145.2(11) ?
C4 C5 C7 F9A . . . . 37.1(12) ?
C2 N11 C12 C17 . . . . 7.9(6) ?
C2 N11 C12 C13 . . . . -173.4(4) ?
N11 C12 C13 C14 . . . . -177.8(3) ?
C17 C12 C13 C14 . . . . 1.1(5) ?
N11 C12 C13 C18 . . . . 4.1(5) ?
C17 C12 C13 C18 . . . . -177.1(3) ?
C12 C13 C14 C15 . . . . -2.1(6) ?
C18 C13 C14 C15 . . . . 176.1(4) ?
C13 C14 C15 C16 . . . . 1.4(7) ?
C14 C15 C16 C17 . . . . 0.4(7) ?
C15 C16 C17 C12 . . . . -1.5(7) ?
N11 C12 C17 C16 . . . . 179.4(4) ?
C13 C12 C17 C16 . . . . 0.7(6) ?
C21 N22 C18 O19 . . . . -2.5(5) ?
C21 N22 C18 C13 . . . . 174.5(4) ?
C20 O19 C18 N22 . . . . -4.6(5) ?
C20 O19 C18 C13 . . . . 178.0(4) ?
C14 C13 C18 N22 . . . . 179.2(4) ?
C12 C13 C18 N22 . . . . -2.6(6) ?
C14 C13 C18 O19 . . . . -3.7(5) ?
C12 C13 C18 O19 . . . . 174.4(3) ?
C18 O19 C20 C21 . . . . 9.2(5) ?
C18 N22 C21 C23 . . . . -115.3(4) ?
C18 N22 C21 C20 . . . . 8.0(5) ?
O19 C20 C21 N22 . . . . -10.3(5) ?
O19 C20 C21 C23 . . . . 111.0(4) ?
N22 C21 C23 C24 . . . . 23.2(6) ?
C20 C21 C23 C24 . . . . -93.5(5) ?
N22 C21 C23 C28 . . . . -157.5(4) ?
C20 C21 C23 C28 . . . . 85.9(5) ?
C28 C23 C24 C25 . . . . 1.1(6) ?
C21 C23 C24 C25 . . . . -179.6(4) ?
C23 C24 C25 C26 . . . . -0.3(7) ?
C24 C25 C26 C27 . . . . -0.4(7) ?
C25 C26 C27 C28 . . . . 0.2(7) ?
C26 C27 C28 C23 . . . . 0.6(7) ?
C24 C23 C28 C27 . . . . -1.2(6) ?
C21 C23 C28 C27 . . . . 179.4(4) ?
