#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/91/1559111.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1559111
loop_
_publ_author_name
'Sun, Xi-Shang'
'Wang, Xing-Heng'
'Tao, Hai-Yan'
'Wei, Liang'
'Wang, Chun-Jiang'
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Quaternary Trifluoromethyl α- to
 ϵ-Amino Acid Derivatives via Umpolung Allylation/2-aza-Cope
 Rearrangement
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04685J
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H18 F3 N O2'
_chemical_formula_sum            'C18 H18 F3 N O2'
_chemical_formula_weight         337.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2020-07-22 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2073(2)
_cell_length_b                   7.63800(10)
_cell_length_c                   34.6279(9)
_cell_measurement_reflns_used    12223
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.3370
_cell_measurement_theta_min      2.5640
_cell_volume                     1641.76(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00   9.00   0.50    0.50    --    0.00  38.00 -60.00   52
  2  ω    -21.00   5.00   0.50    0.50    --    0.00 -82.00-180.00   52
  3  ω     32.00  75.00   0.50    0.50    --    0.00  38.00  30.00   86
  4  ω    -18.00  58.00   0.50    0.50    --    0.00  19.00-180.00  152
  5  ω    -17.00  17.00   0.50    0.50    --    0.00  38.00  30.00   68
  6  ω     48.00  89.00   0.50    0.50    --    0.00  57.00-150.00   82
  7  ω    -22.00  32.00   0.50    0.50    --    0.00  57.00-150.00  108
  8  ω    -16.00  84.00   0.50    0.50    --    0.00  38.00  90.00  200
  9  ω    -16.00  31.00   0.50    0.50    --    0.00  38.00 -30.00   94
 10  ω     60.00  89.00   0.50    0.50    --    0.00  38.00 -30.00   58
 11  ω     68.00  93.00   0.50    0.50    --   94.60  71.00 -98.95   50
 12  ω     68.00  95.00   0.50    0.50    --   94.60  69.00 173.65   54
 13  ω    150.00 179.00   0.50    0.50    --   94.60  69.00 173.65   58
 14  ω     68.00  94.00   0.50    0.50    --   94.60  70.00 -83.13   52
 15  ω     70.00 136.00   0.50    0.50    --   94.60  66.00  94.93  132
 16  ω    135.00 183.00   0.50    0.50    --   94.60  40.00  23.48   96
 17  ω     69.00  95.00   0.50    0.50    --   94.60  66.00-149.97   52
 18  ω     67.00 180.00   0.50    0.50    --   94.60  75.00 -63.50  226
 19  ω     67.00 147.00   0.50    0.50    --   94.60  72.00-169.82  160
 20  ω    107.00 184.00   0.50    0.50    --   94.60  59.00 130.27  154
 21  ω     69.00  95.00   0.50    0.50    --   94.60  66.00 158.35   52
 22  ω     66.00  98.00   0.50    0.50    --   94.60  74.00  65.98   64
 23  ω     71.00 103.00   0.50    0.50    --   94.60  61.00  46.77   64
 24  ω    134.00 183.00   0.50    0.50    --   94.60  61.00  46.77   98
 25  ω     68.00  94.00   0.50    0.50    --   94.60  69.00-130.47   52
 26  ω    120.00 146.00   0.50    0.50    --   94.60  69.00-130.47   52
 27  ω    156.00 182.00   0.50    0.50    --   94.60  69.00-130.47   52
 28  ω     66.00  92.00   0.50    0.50    --   94.60  74.00-115.68   52
 29  ω     77.00 104.00   0.50    0.50    --   94.60  40.00  23.48   54
 30  ω     17.00 126.00   0.50    0.50    --   94.60 -82.00  30.00  218
 31  ω     71.00  98.00   0.50    0.50    --   94.60  59.00 130.27   54
 32  ω     67.00 129.00   0.50    0.50    --   94.60  71.00 -71.42  124
 33  ω    113.00 179.00   0.50    0.50    --   94.60  69.00 -43.75  132
 34  ω     72.00  97.00   0.50    0.50    --   94.60  61.00  60.00   50
 35  ω     70.00  96.00   0.50    0.50    --   94.60  63.00 139.92   52
 36  ω     71.00  97.00   0.50    0.50    --   94.60  61.00  30.00   52
 37  ω     71.00  96.00   0.50    0.50    --   94.60  61.00   0.00   50
 38  ω    124.00 184.00   0.50    0.50    --   94.60  61.00   0.00  120
 39  ω     55.00 112.00   0.50    0.50    --   94.60 -61.00 120.00  114
 40  ω     70.00 131.00   0.50    0.50    --   94.60  63.00 177.22  122
 41  ω     74.00 102.00   0.50    0.50    --   94.60  61.00 150.00   56
 42  ω    106.00 184.00   0.50    0.50    --   94.60  70.00 105.13  156
 43  ω     77.00 102.00   0.50    0.50    --   94.60  45.00   0.00   50
 44  ω     72.00  97.00   0.50    0.50    --   94.60  61.00  90.00   50
 45  ω     29.00  63.00   0.50    0.50    --   94.60 -82.00 -60.00   68
 46  ω     75.00 126.00   0.50    0.50    --   94.60 -82.00 -60.00  102
 47  ω     51.00 126.00   0.50    0.50    --   94.60 -82.00 120.00  150
 48  ω     68.00  93.00   0.50    0.50    --   94.60  70.00 105.13   50
 49  ω     69.00  95.00   0.50    0.50    --   94.60  69.00 -43.75   52
 50  ω     71.00 177.00   0.50    0.50    --   94.60  63.00-138.06  212
 51  ω     75.00 116.00   0.50    0.50    --   94.60  47.00  33.33   82
 52  ω     22.00 114.00   0.50    0.50    --   94.60 -82.00 -90.00  184
 53  ω     68.00 181.00   0.50    0.50    --   94.60  69.00-116.74  226
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0126550000
_diffrn_orient_matrix_UB_12      -0.0871154000
_diffrn_orient_matrix_UB_13      -0.0400346000
_diffrn_orient_matrix_UB_21      -0.0277903000
_diffrn_orient_matrix_UB_22      -0.1812733000
_diffrn_orient_matrix_UB_23      0.0189126000
_diffrn_orient_matrix_UB_31      -0.2463053000
_diffrn_orient_matrix_UB_32      0.0159414000
_diffrn_orient_matrix_UB_33      -0.0042081000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            28850
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         2.55
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.1262
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1500P)²+4.0870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3226
_refine_ls_wR_factor_ref         0.3242
_reflns_number_gt                2797
_reflns_number_total             2904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0sc04685j2.cif
_cod_data_source_block           20190409_sxs-8-13
_cod_database_code               1559111
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C17
 1.5 with sigma of 0.02
 O2-C17
 1.5 with sigma of 0.02
 C16-O2
 1.4 with sigma of 0.02
 C16-O1
 1.4 with sigma of 0.02
3.a Rotating group:
 N1(H1A,H1B)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.893
_oxdiff_exptl_absorpt_empirical_full_min 0.356
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F -1.107(2) -0.6358(14) 0.1839(3) 0.262(8) Uani 1 d . . .
F2 F -1.1167(14) -0.8676(10) 0.2192(2) 0.146(3) Uani 1 d . . .
F3 F -0.867(2) -0.6828(14) 0.2232(2) 0.199(6) Uani 1 d . . .
O1 O -0.817(2) -1.1515(13) 0.1728(3) 0.176(6) Uani 1 d . . D
O2 O -0.6143(11) -0.9901(14) 0.2085(2) 0.148(4) Uani 1 d . . D
C1 C -0.3251(10) -0.9740(7) 0.04936(18) 0.0429(13) Uani 1 d . . .
H1 H -0.2550 -0.9715 0.0731 0.051 Uiso 1 calc . . R
C2 C -0.2301(10) -1.0555(7) 0.01940(19) 0.0455(14) Uani 1 d . . .
H2 H -0.0941 -1.1044 0.0227 0.055 Uiso 1 calc . . R
C3 C -0.3324(10) -1.0685(7) -0.01690(19) 0.0436(14) Uani 1 d . . .
C4 C -0.2361(10) -1.1571(7) -0.0483(2) 0.0492(16) Uani 1 d . . .
H4 H -0.1016 -1.2091 -0.0453 0.059 Uiso 1 calc . . R
C5 C -0.3403(13) -1.1667(8) -0.0831(2) 0.0572(18) Uani 1 d . . .
H5 H -0.2745 -1.2229 -0.1038 0.069 Uiso 1 calc . . R
C6 C -0.5430(15) -1.0934(10) -0.0877(2) 0.072(2) Uani 1 d . . .
H6 H -0.6153 -1.1067 -0.1110 0.086 Uiso 1 calc . . R
C7 C -0.6387(12) -1.0010(8) -0.05803(18) 0.0492(15) Uani 1 d . . .
H7 H -0.7689 -0.9441 -0.0624 0.059 Uiso 1 calc . . R
C8 C -0.5440(9) -0.9918(7) -0.02203(17) 0.0372(12) Uani 1 d . . .
C9 C -0.6356(11) -0.9048(7) 0.01073(17) 0.0448(14) Uani 1 d . . .
H9 H -0.7718 -0.8553 0.0083 0.054 Uiso 1 calc . . R
C10 C -0.5302(9) -0.8915(7) 0.04577(17) 0.0418(13) Uani 1 d . . .
C11 C -0.6370(13) -0.8112(9) 0.07850(19) 0.0566(17) Uani 1 d . . .
H11 H -0.7538 -0.7403 0.0723 0.068 Uiso 1 calc . . R
C12 C -0.5946(15) -0.8231(11) 0.1148(2) 0.069(2) Uani 1 d . . .
H12 H -0.4823 -0.8974 0.1217 0.082 Uiso 1 calc . . R
C13 C -0.7064(19) -0.7301(11) 0.1470(2) 0.086(3) Uani 1 d . . .
H13A H -0.7808 -0.6281 0.1370 0.103 Uiso 1 calc . . R
H13B H -0.6011 -0.6905 0.1658 0.103 Uiso 1 calc . . R
C14 C -0.8684(13) -0.8517(13) 0.16666(19) 0.073(2) Uani 1 d . . .
C15 C -0.985(3) -0.7552(17) 0.1984(3) 0.144(7) Uani 1 d . . .
C16 C -0.7611(16) -1.0008(14) 0.1847(3) 0.102(4) Uani 1 d . . D
C17 C -0.550(2) -1.189(2) 0.2170(4) 0.199(11) Uani 1 d . . D
H17A H -0.4832 -1.1940 0.2423 0.239 Uiso 1 calc . . R
H17B H -0.6817 -1.2573 0.2183 0.239 Uiso 1 calc . . R
C18 C -0.4044(19) -1.2742(16) 0.1891(3) 0.110(4) Uani 1 d . . .
H18A H -0.4795 -1.2935 0.1652 0.166 Uiso 1 calc . . GR
H18B H -0.3567 -1.3843 0.1993 0.166 Uiso 1 calc . . GR
H18C H -0.2820 -1.2001 0.1845 0.166 Uiso 1 calc . . GR
N1 N -1.0242(11) -0.922(2) 0.1403(2) 0.156(6) Uani 1 d . . .
H1A H -1.1239 -0.9805 0.1523 0.187 Uiso 1 d . . GR
H1B H -1.0855 -0.8359 0.1280 0.187 Uiso 1 d . . GR
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'
F F 0.0727 0.0534 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 C17 104.2(10) . . ?
C2 C1 C10 121.9(6) . . ?
C1 C2 C3 121.4(5) . . ?
C2 C3 C4 121.9(6) . . ?
C2 C3 C8 119.2(5) . . ?
C4 C3 C8 118.9(6) . . ?
C5 C4 C3 120.1(6) . . ?
C4 C5 C6 120.6(7) . . ?
C7 C6 C5 120.7(8) . . ?
C8 C7 C6 121.0(7) . . ?
C7 C8 C3 118.4(5) . . ?
C7 C8 C9 124.8(5) . . ?
C9 C8 C3 116.8(5) . . ?
C10 C9 C8 122.8(6) . . ?
C1 C10 C11 121.8(6) . . ?
C9 C10 C1 117.8(6) . . ?
C9 C10 C11 120.1(6) . . ?
C12 C11 C10 129.8(8) . . ?
C11 C12 C13 126.9(9) . . ?
C12 C13 C14 110.4(7) . . ?
C15 C14 C13 110.0(10) . . ?
C16 C14 C13 111.4(7) . . ?
C16 C14 C15 106.7(7) . . ?
N1 C14 C13 112.8(7) . . ?
N1 C14 C15 108.8(10) . . ?
N1 C14 C16 106.9(11) . . ?
F1 C15 F2 107.0(13) . . ?
F1 C15 C14 110.1(9) . . ?
F2 C15 C14 111.1(11) . . ?
F3 C15 F1 107.4(14) . . ?
F3 C15 F2 105.1(9) . . ?
F3 C15 C14 115.7(14) . . ?
O1 C16 C14 116.3(11) . . ?
O2 C16 O1 118.6(10) . . ?
O2 C16 C14 125.0(11) . . ?
C18 C17 O2 116.8(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.290(13) . ?
F2 C15 1.389(16) . ?
F3 C15 1.26(2) . ?
O1 C16 1.271(13) . ?
O2 C16 1.230(12) . ?
O2 C17 1.598(12) . ?
C1 C2 1.346(9) . ?
C1 C10 1.426(8) . ?
C2 C3 1.412(9) . ?
C3 C4 1.412(9) . ?
C3 C8 1.449(8) . ?
C4 C5 1.370(10) . ?
C5 C6 1.387(12) . ?
C6 C7 1.381(11) . ?
C7 C8 1.380(8) . ?
C8 C9 1.432(8) . ?
C9 C10 1.382(8) . ?
C10 C11 1.449(9) . ?
C11 C12 1.288(10) . ?
C12 C13 1.493(11) . ?
C13 C14 1.528(13) . ?
C14 C15 1.507(12) . ?
C14 C16 1.460(11) . ?
C14 N1 1.432(12) . ?
C17 C18 1.475(13) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306758
