# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Zhang, Xingang'
_publ_contact_author_email       xgzhang@mail.sioc.ac.cn

_publ_section_title              
;
Highly diastereoselective synthesis of quaternary alfa-trifluoromethyl
alfa-amino acids from chiral imines of trifluoropyruvate
;
loop_
_publ_author_name
'Qiao-Qiao Min'
'Chun-Yang He'
'Haibing Zhou'
'Xingang Zhang'

# Attachment '- 4j.cif'

data_cd29475
_database_code_depnum_ccdc_archive 'CCDC 782838'
#TrackingRef '- 4j.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 F3 N O2'
_chemical_formula_weight         361.35

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8902(10)
_cell_length_b                   12.4068(16)
_cell_length_c                   9.9490(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.018(2)
_cell_angle_gamma                90.00
_cell_volume                     896.39(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2195
_cell_measurement_theta_min      5.529
_cell_measurement_theta_max      54.451

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.39173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4734
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1749
_reflns_number_gt                1592
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1749
_refine_ls_number_parameters     240
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4301(3) 0.59672(18) 0.5588(2) 0.0407(5) Uani 1 1 d D . .
O1 O 0.4223(3) 0.32765(16) 0.4233(2) 0.0607(6) Uani 1 1 d . . .
O2 O 0.3241(3) 0.38647(17) 0.5853(3) 0.0688(6) Uani 1 1 d . . .
F1 F 0.1678(2) 0.52424(18) 0.2819(2) 0.0739(6) Uani 1 1 d . . .
F2 F 0.3886(2) 0.49113(17) 0.21277(16) 0.0668(5) Uani 1 1 d . . .
F3 F 0.3547(2) 0.64897(15) 0.28399(17) 0.0653(5) Uani 1 1 d . . .
C1 C 0.4673(3) 0.5158(2) 0.4692(3) 0.0397(6) Uani 1 1 d . . .
C2 C 0.4024(3) 0.4022(2) 0.4902(3) 0.0483(6) Uani 1 1 d . . .
C3 C 0.2817(5) 0.4761(2) 0.6610(4) 0.0600(8) Uani 1 1 d . . .
H3A H 0.2735 0.4503 0.7503 0.072 Uiso 1 1 calc R . .
H3B H 0.1633 0.5066 0.5999 0.072 Uiso 1 1 calc R . .
C4 C 0.4276(4) 0.5615(2) 0.6968(3) 0.0452(6) Uani 1 1 d . . .
H4 H 0.5475 0.5308 0.7580 0.054 Uiso 1 1 calc R . .
C5 C 0.6743(3) 0.5066(2) 0.4857(3) 0.0408(6) Uani 1 1 d . . .
H5 H 0.6803 0.4478 0.4218 0.049 Uiso 1 1 calc R . .
C6 C 0.7381(4) 0.6072(2) 0.4358(3) 0.0499(6) Uani 1 1 d . . .
H6 H 0.7280 0.6724 0.4783 0.060 Uiso 1 1 calc R . .
C7 C 0.8073(5) 0.6080(3) 0.3356(4) 0.0740(10) Uani 1 1 d . . .
H7A H 0.8189 0.5439 0.2915 0.089 Uiso 1 1 calc R . .
H7B H 0.8448 0.6726 0.3087 0.089 Uiso 1 1 calc R . .
C8 C 0.3829(4) 0.6539(2) 0.7756(3) 0.0516(7) Uani 1 1 d . . .
C9 C 0.2322(4) 0.7196(3) 0.7064(4) 0.0595(8) Uani 1 1 d . . .
H9 H 0.1588 0.7084 0.6083 0.071 Uiso 1 1 calc R . .
C10 C 0.1902(6) 0.8012(3) 0.7812(5) 0.0831(11) Uani 1 1 d . . .
H10 H 0.0885 0.8449 0.7333 0.100 Uiso 1 1 calc R . .
C11 C 0.2962(9) 0.8191(4) 0.9254(7) 0.1082(17) Uani 1 1 d . . .
H11 H 0.2680 0.8748 0.9757 0.130 Uiso 1 1 calc R . .
C12 C 0.4443(9) 0.7538(5) 0.9944(6) 0.1172(18) Uani 1 1 d . . .
H12 H 0.5159 0.7645 1.0930 0.141 Uiso 1 1 calc R . .
C13 C 0.4887(6) 0.6733(4) 0.9212(4) 0.0830(11) Uani 1 1 d . . .
H13 H 0.5916 0.6307 0.9698 0.100 Uiso 1 1 calc R . .
C14 C 0.8000(3) 0.4760(2) 0.6413(3) 0.0410(6) Uani 1 1 d . . .
C15 C 0.8406(4) 0.3689(2) 0.6780(3) 0.0473(6) Uani 1 1 d . . .
H15 H 0.7883 0.3160 0.6076 0.057 Uiso 1 1 calc R . .
C16 C 0.9567(4) 0.3388(3) 0.8168(3) 0.0591(8) Uani 1 1 d . . .
H16 H 0.9814 0.2663 0.8398 0.071 Uiso 1 1 calc R . .
C17 C 1.0361(4) 0.4162(3) 0.9212(3) 0.0654(9) Uani 1 1 d . . .
H17 H 1.1152 0.3964 1.0149 0.078 Uiso 1 1 calc R . .
C18 C 0.9987(4) 0.5224(3) 0.8869(3) 0.0665(9) Uani 1 1 d . . .
H18 H 1.0526 0.5746 0.9579 0.080 Uiso 1 1 calc R . .
C19 C 0.8818(4) 0.5534(3) 0.7483(3) 0.0537(7) Uani 1 1 d . . .
H19 H 0.8578 0.6262 0.7265 0.064 Uiso 1 1 calc R . .
C20 C 0.3450(4) 0.5449(3) 0.3104(3) 0.0507(7) Uani 1 1 d . . .
H1 H 0.484(4) 0.6539(17) 0.563(3) 0.046(8) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0465(11) 0.0321(12) 0.0525(12) -0.0027(10) 0.0289(9) -0.0029(10)
O1 0.0658(13) 0.0390(11) 0.0867(14) -0.0159(10) 0.0401(11) -0.0040(10)
O2 0.0858(15) 0.0416(12) 0.1094(17) -0.0085(11) 0.0711(14) -0.0144(11)
F1 0.0365(8) 0.1028(16) 0.0734(11) -0.0063(10) 0.0118(7) 0.0023(9)
F2 0.0657(10) 0.0831(13) 0.0496(8) -0.0153(9) 0.0203(7) 0.0090(9)
F3 0.0708(11) 0.0648(13) 0.0600(9) 0.0131(8) 0.0254(8) 0.0150(9)
C1 0.0370(11) 0.0370(14) 0.0490(13) -0.0032(10) 0.0210(10) -0.0018(10)
C2 0.0381(13) 0.0424(16) 0.0672(16) -0.0045(13) 0.0234(12) -0.0038(11)
C3 0.0730(17) 0.0436(16) 0.089(2) -0.0004(15) 0.0597(16) -0.0031(14)
C4 0.0471(13) 0.0442(15) 0.0532(14) 0.0068(12) 0.0293(12) 0.0036(11)
C5 0.0374(11) 0.0434(14) 0.0475(12) -0.0052(11) 0.0232(10) 0.0017(11)
C6 0.0448(13) 0.0481(16) 0.0629(15) -0.0005(13) 0.0276(12) 0.0004(12)
C7 0.079(2) 0.076(3) 0.088(2) 0.013(2) 0.0550(19) -0.0031(19)
C8 0.0566(15) 0.0529(18) 0.0594(15) -0.0026(13) 0.0379(13) -0.0071(14)
C9 0.0617(17) 0.0538(19) 0.0779(19) -0.0021(15) 0.0433(15) 0.0015(14)
C10 0.097(3) 0.053(2) 0.135(4) -0.001(2) 0.085(3) 0.0032(19)
C11 0.166(5) 0.074(3) 0.139(4) -0.036(3) 0.119(4) -0.014(3)
C12 0.170(5) 0.117(4) 0.087(3) -0.039(3) 0.074(3) -0.017(4)
C13 0.102(3) 0.090(3) 0.0592(19) -0.009(2) 0.0334(18) 0.003(2)
C14 0.0313(11) 0.0479(15) 0.0502(13) -0.0073(12) 0.0230(10) -0.0031(11)
C15 0.0438(13) 0.0510(17) 0.0482(14) -0.0035(12) 0.0192(11) -0.0060(12)
C16 0.0562(16) 0.064(2) 0.0578(17) 0.0069(15) 0.0230(14) -0.0002(15)
C17 0.0592(17) 0.086(3) 0.0482(16) 0.0014(17) 0.0179(13) -0.0074(18)
C18 0.0526(16) 0.087(3) 0.0563(17) -0.0223(17) 0.0173(13) -0.0158(17)
C19 0.0463(14) 0.0558(18) 0.0634(17) -0.0121(14) 0.0260(13) -0.0063(13)
C20 0.0449(14) 0.0537(18) 0.0536(15) -0.0077(13) 0.0193(12) 0.0049(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C1 1.447(3) . ?
N1 C4 1.449(3) . ?
N1 H1 0.819(18) . ?
O1 C2 1.186(3) . ?
O2 C2 1.331(3) . ?
O2 C3 1.453(4) . ?
F1 C20 1.338(3) . ?
F2 C20 1.330(3) . ?
F3 C20 1.326(4) . ?
C1 C20 1.538(4) . ?
C1 C2 1.542(4) . ?
C1 C5 1.581(3) . ?
C3 C4 1.501(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C8 1.507(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.501(4) . ?
C5 C14 1.524(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.311(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9300 . ?
C7 H7B 0.9300 . ?
C8 C13 1.381(5) . ?
C8 C9 1.383(4) . ?
C9 C10 1.372(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 C19 1.391(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
C1 N1 C4 117.1(2) . . ?
C1 N1 H1 114(2) . . ?
C4 N1 H1 114.6(19) . . ?
C2 O2 C3 121.4(2) . . ?
N1 C1 C20 105.8(2) . . ?
N1 C1 C2 113.1(2) . . ?
C20 C1 C2 104.2(2) . . ?
N1 C1 C5 115.88(19) . . ?
C20 C1 C5 109.36(19) . . ?
C2 C1 C5 107.7(2) . . ?
O1 C2 O2 119.1(3) . . ?
O1 C2 C1 120.8(2) . . ?
O2 C2 C1 120.1(2) . . ?
O2 C3 C4 110.6(2) . . ?
O2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 106.3(2) . . ?
N1 C4 C8 110.9(2) . . ?
C3 C4 C8 110.3(2) . . ?
N1 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C8 C4 H4 109.8 . . ?
C6 C5 C14 111.9(2) . . ?
C6 C5 C1 111.8(2) . . ?
C14 C5 C1 111.06(18) . . ?
C6 C5 H5 107.2 . . ?
C14 C5 H5 107.2 . . ?
C1 C5 H5 107.2 . . ?
C7 C6 C5 123.4(3) . . ?
C7 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C6 C7 H7A 120.0 . . ?
C6 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
C13 C8 C9 118.0(3) . . ?
C13 C8 C4 120.6(3) . . ?
C9 C8 C4 121.3(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 118.9(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 120.8(5) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C15 C14 C19 118.1(3) . . ?
C15 C14 C5 119.9(2) . . ?
C19 C14 C5 121.9(3) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
F3 C20 F2 107.0(2) . . ?
F3 C20 F1 106.3(2) . . ?
F2 C20 F1 107.2(2) . . ?
F3 C20 C1 111.8(2) . . ?
F2 C20 C1 113.2(2) . . ?
F1 C20 C1 110.9(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C20 143.1(2) . . . . ?
C4 N1 C1 C2 29.5(3) . . . . ?
C4 N1 C1 C5 -95.6(3) . . . . ?
C3 O2 C2 O1 -174.6(3) . . . . ?
C3 O2 C2 C1 5.9(4) . . . . ?
N1 C1 C2 O1 179.5(2) . . . . ?
C20 C1 C2 O1 65.0(3) . . . . ?
C5 C1 C2 O1 -51.1(3) . . . . ?
N1 C1 C2 O2 -1.1(4) . . . . ?
C20 C1 C2 O2 -115.6(3) . . . . ?
C5 C1 C2 O2 128.3(3) . . . . ?
C2 O2 C3 C4 -36.3(4) . . . . ?
C1 N1 C4 C3 -58.7(3) . . . . ?
C1 N1 C4 C8 -178.7(2) . . . . ?
O2 C3 C4 N1 59.9(3) . . . . ?
O2 C3 C4 C8 -179.8(2) . . . . ?
N1 C1 C5 C6 -64.4(3) . . . . ?
C20 C1 C5 C6 55.1(3) . . . . ?
C2 C1 C5 C6 167.8(2) . . . . ?
N1 C1 C5 C14 61.4(3) . . . . ?
C20 C1 C5 C14 -179.1(2) . . . . ?
C2 C1 C5 C14 -66.4(3) . . . . ?
C14 C5 C6 C7 110.4(3) . . . . ?
C1 C5 C6 C7 -124.3(3) . . . . ?
N1 C4 C8 C13 -131.6(3) . . . . ?
C3 C4 C8 C13 110.9(3) . . . . ?
N1 C4 C8 C9 50.5(3) . . . . ?
C3 C4 C8 C9 -67.0(3) . . . . ?
C13 C8 C9 C10 -0.1(5) . . . . ?
C4 C8 C9 C10 177.9(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C10 C11 C12 C13 1.2(8) . . . . ?
C11 C12 C13 C8 -1.4(7) . . . . ?
C9 C8 C13 C12 0.8(6) . . . . ?
C4 C8 C13 C12 -177.2(4) . . . . ?
C6 C5 C14 C15 -141.4(2) . . . . ?
C1 C5 C14 C15 92.9(3) . . . . ?
C6 C5 C14 C19 36.5(3) . . . . ?
C1 C5 C14 C19 -89.3(3) . . . . ?
C19 C14 C15 C16 0.7(4) . . . . ?
C5 C14 C15 C16 178.6(2) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C14 0.1(5) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
C5 C14 C19 C18 -178.3(2) . . . . ?
N1 C1 C20 F3 46.6(3) . . . . ?
C2 C1 C20 F3 166.2(2) . . . . ?
C5 C1 C20 F3 -78.8(3) . . . . ?
N1 C1 C20 F2 167.6(2) . . . . ?
C2 C1 C20 F2 -72.9(3) . . . . ?
C5 C1 C20 F2 42.1(3) . . . . ?
N1 C1 C20 F1 -71.8(3) . . . . ?
C2 C1 C20 F1 47.7(3) . . . . ?
C5 C1 C20 F1 162.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.819(18) 2.266(19) 3.071(3) 168(3) 2_656

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.033