# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182

_publ_contact_author_email       KAJ@CHEM.AU.DK

_publ_section_title              
;Enantioselective Organocatalytic Substitution of
?-Cyanoacetates on Imidoyl Chlorides - Synthesis of Optically Active
Ketimines
;
_publ_contact_author_name        'Prof. Karl Anker Jorgensen'
loop_
_publ_author_name
S.Santoro
T.B.Poulsen
K.A.Jorgensen

data_07jo0042_0m
_database_code_depnum_ccdc_archive 'CCDC 663280'

_audit_creation_date             2007-09-20T11:08:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C20 H18 F3 N3 O5'
_chemical_formula_sum            'C20 H18 F3 N3 O5'
_chemical_formula_weight         437.37
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2352(4)
_cell_length_b                   14.0673(5)
_cell_length_c                   17.2845(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2002.36(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    91(1)
_cell_measurement_reflns_used    2920
_cell_measurement_theta_min      5.12
_cell_measurement_theta_max      64.31
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  0.901

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      91(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       '\f-scans and \w-scans'
_diffrn_detector_area_resol_mean 0.0833
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_number            2538
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         65.31
_diffrn_reflns_theta_full        65.31
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.813
_reflns_number_total             2538
_reflns_number_gt                2398
_reflns_threshold_expression     >2sigma(I)
_diffrn_reflns_reduction_process 
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0503P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2538
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.031
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 928 Friedel pairs'
_refine_ls_abs_structure_Flack   0.08(14)
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_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
C1 C 0.4277(3) 0.25447(14) 0.10214(14) 0.0187(5) Uani 1 1 d . . .
C2 C 0.4007(3) 0.16834(14) 0.06572(13) 0.0226(6) Uani 1 1 d . . .
H2 H 0.4877 0.1333 0.0467 0.027 Uiso 1 1 calc R . .
C3 C 0.2446(3) 0.13474(14) 0.05775(13) 0.0257(6) Uani 1 1 d . . .
H3 H 0.226 0.0764 0.0341 0.031 Uiso 1 1 calc R . .
C4 C 0.1156(3) 0.18778(14) 0.08495(13) 0.0234(6) Uani 1 1 d . . .
H4 H 0.0101 0.166 0.0778 0.028 Uiso 1 1 calc R . .
C5 C 0.1421(3) 0.27354(14) 0.12293(14) 0.0214(6) Uani 1 1 d . . .
H5 H 0.0545 0.3074 0.1427 0.026 Uiso 1 1 calc R . .
C6 C 0.2990(3) 0.30896(13) 0.13147(13) 0.0177(5) Uani 1 1 d . . .
C7 C 0.2867(3) 0.47243(13) 0.16583(13) 0.0174(5) Uani 1 1 d . . .
C8 C 0.2195(3) 0.50515(14) 0.08843(14) 0.0223(6) Uani 1 1 d . . .
C9 C 0.3067(3) 0.54716(12) 0.22931(13) 0.0161(5) Uani 1 1 d . . .
C10 C 0.3953(3) 0.50403(14) 0.29497(15) 0.0193(5) Uani 1 1 d . . .
C11 C 0.1398(3) 0.58315(13) 0.25978(14) 0.0200(5) Uani 1 1 d . . .
H11A H 0.1583 0.6286 0.301 0.024 Uiso 1 1 calc R . .
H11B H 0.0838 0.6159 0.2183 0.024 Uiso 1 1 calc R . .
C12 C 0.0340(3) 0.50554(14) 0.28930(14) 0.0196(6) Uani 1 1 d . . .
C13 C 0.0272(3) 0.45550(15) 0.35506(15) 0.0261(6) Uani 1 1 d . . .
H13 H 0.0926 0.4637 0.3984 0.031 Uiso 1 1 calc R . .
C14 C -0.0992(3) 0.38719(14) 0.34606(14) 0.0242(6) Uani 1 1 d . . .
H14 H -0.1328 0.3427 0.3825 0.029 Uiso 1 1 calc R . .
C15 C -0.1598(3) 0.39954(15) 0.27526(15) 0.0292(6) Uani 1 1 d . . .
H15 H -0.2441 0.3642 0.2539 0.035 Uiso 1 1 calc R . .
C16 C 0.4122(3) 0.63220(13) 0.20146(13) 0.0200(6) Uani 1 1 d . . .
C17 C 0.6401(3) 0.66840(14) 0.11466(14) 0.0205(6) Uani 1 1 d . . .
C18 C 0.7363(3) 0.60039(14) 0.06452(14) 0.0268(6) Uani 1 1 d . . .
H18A H 0.8196 0.6348 0.0376 0.04 Uiso 1 1 calc R . .
H18B H 0.665 0.5709 0.0277 0.04 Uiso 1 1 calc R . .
H18C H 0.7851 0.5525 0.0965 0.04 Uiso 1 1 calc R . .
C19 C 0.7439(3) 0.71203(15) 0.17794(15) 0.0263(6) Uani 1 1 d . . .
H19A H 0.6811 0.7579 0.2061 0.039 Uiso 1 1 calc R . .
H19B H 0.8364 0.7427 0.1552 0.039 Uiso 1 1 calc R . .
H19C H 0.78 0.663 0.2126 0.039 Uiso 1 1 calc R . .
C20 C 0.5500(3) 0.74121(15) 0.06663(15) 0.0290(7) Uani 1 1 d . . .
H20A H 0.4858 0.7808 0.1 0.043 Uiso 1 1 calc R . .
H20B H 0.4803 0.7093 0.0305 0.043 Uiso 1 1 calc R . .
H20C H 0.6266 0.7798 0.0389 0.043 Uiso 1 1 calc R . .
N1 N 0.4598(3) 0.47535(12) 0.34885(13) 0.0265(5) Uani 1 1 d . . .
N2 N 0.3258(2) 0.38775(11) 0.18059(11) 0.0169(5) Uani 1 1 d . . .
N3 N 0.5941(3) 0.28730(12) 0.10848(11) 0.0219(5) Uani 1 1 d . . .
O1 O 0.7044(2) 0.22921(10) 0.10050(10) 0.0295(4) Uani 1 1 d . . .
O2 O 0.6180(2) 0.37267(10) 0.12098(9) 0.0264(4) Uani 1 1 d . . .
O3 O 0.51920(19) 0.60188(9) 0.15095(9) 0.0190(4) Uani 1 1 d . . .
O4 O 0.3923(2) 0.71190(9) 0.22589(9) 0.0263(4) Uani 1 1 d . . .
O5 O -0.0793(2) 0.47240(10) 0.23838(9) 0.0282(4) Uani 1 1 d . . .
F1 F 0.20486(18) 0.60000(8) 0.08348(8) 0.0285(4) Uani 1 1 d . . .
F2 F 0.07178(17) 0.46965(8) 0.07431(8) 0.0277(3) Uani 1 1 d . . .
F3 F 0.31547(18) 0.47734(9) 0.03028(8) 0.0324(4) Uani 1 1 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
C1 0.0209(14) 0.0162(10) 0.0190(14) 0.0040(9) -0.0041(12) 0.0007(10)
C2 0.0335(16) 0.0157(10) 0.0186(14) 0.0008(9) 0.0011(13) 0.0059(11)
C3 0.0396(18) 0.0123(11) 0.0251(15) -0.0023(9) -0.0028(13) 0.0002(10)
C4 0.0299(15) 0.0200(11) 0.0202(14) 0.0021(9) -0.0051(13) -0.0076(11)
C5 0.0255(16) 0.0179(11) 0.0207(15) 0.0007(10) 0.0001(12) -0.0007(9)
C6 0.0271(14) 0.0119(10) 0.0141(13) 0.0011(9) 0.0012(12) 0.0007(10)
C7 0.0154(13) 0.0167(11) 0.0202(14) 0.0018(9) 0.0036(11) -0.0003(9)
C8 0.0239(15) 0.0137(11) 0.0295(16) -0.0023(9) 0.0010(13) 0.0012(10)
C9 0.0175(12) 0.0120(9) 0.0188(13) -0.0022(9) 0.0000(12) -0.0002(9)
C10 0.0228(14) 0.0132(10) 0.0219(15) -0.0046(10) 0.0043(13) -0.0007(10)
C11 0.0209(13) 0.0138(10) 0.0253(14) -0.0023(9) 0.0001(12) 0.0012(9)
C12 0.0157(13) 0.0187(11) 0.0245(14) -0.0075(10) 0.0004(11) 0.0011(9)
C13 0.0267(15) 0.0279(12) 0.0237(16) -0.0014(10) -0.0024(13) -0.0050(11)
C14 0.0241(14) 0.0246(11) 0.0238(15) 0.0017(10) 0.0032(13) -0.0004(11)
C15 0.0267(15) 0.0270(12) 0.0339(17) 0.0011(11) 0.0041(14) -0.0131(10)
C16 0.0228(14) 0.0154(11) 0.0219(15) -0.0014(9) 0.0001(13) 0.0012(10)
C17 0.0236(14) 0.0136(10) 0.0245(14) 0.0025(9) 0.0058(12) -0.0039(9)
C18 0.0300(17) 0.0186(12) 0.0319(16) -0.0003(9) 0.0088(13) -0.0016(10)
C19 0.0219(16) 0.0262(12) 0.0307(16) -0.0013(10) 0.0022(12) -0.0059(10)
C20 0.0343(17) 0.0196(11) 0.0331(17) 0.0025(10) 0.0013(14) 0.0006(10)
N1 0.0263(13) 0.0201(9) 0.0330(14) -0.0021(9) -0.0026(12) 0.0002(9)
N2 0.0159(11) 0.0155(9) 0.0193(11) -0.0009(7) 0.0013(9) -0.0002(8)
N3 0.0261(12) 0.0219(10) 0.0177(12) 0.0006(8) 0.0012(10) 0.0038(9)
O1 0.0258(10) 0.0307(9) 0.0318(11) 0.0031(7) 0.0037(9) 0.0130(8)
O2 0.0267(11) 0.0208(8) 0.0316(10) -0.0018(7) 0.0010(9) -0.0024(7)
O3 0.0209(10) 0.0125(7) 0.0236(10) -0.0018(6) 0.0038(8) -0.0005(6)
O4 0.0310(10) 0.0150(8) 0.0329(10) -0.0046(7) 0.0067(9) -0.0014(7)
O5 0.0285(10) 0.0301(8) 0.0259(10) 0.0051(7) -0.0050(9) -0.0102(7)
F1 0.0352(9) 0.0142(6) 0.0362(9) 0.0040(5) -0.0108(7) 0.0009(6)
F2 0.0278(9) 0.0222(7) 0.0332(8) 0.0006(5) -0.0109(7) -0.0029(6)
F3 0.0412(10) 0.0347(7) 0.0213(8) 0.0036(6) 0.0031(8) 0.0094(7)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
C1 C2 1.383(3) . ?
C1 C6 1.402(3) . ?
C1 N3 1.450(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.93 . ?
C3 C4 1.380(3) . ?
C3 H3 0.93 . ?
C4 C5 1.391(3) . ?
C4 H4 0.93 . ?
C5 C6 1.393(3) . ?
C5 H5 0.93 . ?
C6 N2 1.414(3) . ?
C7 N2 1.260(2) . ?
C7 C8 1.519(3) . ?
C7 C9 1.528(3) . ?
C8 F3 1.337(3) . ?
C8 F2 1.337(3) . ?
C8 F1 1.342(2) . ?
C9 C10 1.479(3) . ?
C9 C16 1.555(3) . ?
C9 C11 1.557(3) . ?
C10 N1 1.145(3) . ?
C11 C12 1.487(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.338(3) . ?
C12 O5 1.365(3) . ?
C13 C14 1.425(3) . ?
C13 H13 0.93 . ?
C14 C15 1.333(3) . ?
C14 H14 0.93 . ?
C15 O5 1.377(3) . ?
C15 H15 0.93 . ?
C16 O4 1.209(2) . ?
C16 O3 1.312(3) . ?
C17 O3 1.504(3) . ?
C17 C20 1.513(3) . ?
C17 C18 1.514(3) . ?
C17 C19 1.518(3) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
N3 O1 1.230(2) . ?
N3 O2 1.236(2) . ?

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
C2 C1 C6 121.5(2) . . ?
C2 C1 N3 117.7(2) . . ?
C6 C1 N3 120.82(19) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120 . . ?
C4 C3 H3 120 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 117.85(18) . . ?
C5 C6 N2 119.3(2) . . ?
C1 C6 N2 121.9(2) . . ?
N2 C7 C8 123.91(19) . . ?
N2 C7 C9 118.51(19) . . ?
C8 C7 C9 117.58(17) . . ?
F3 C8 F2 106.93(18) . . ?
F3 C8 F1 107.21(18) . . ?
F2 C8 F1 106.14(18) . . ?
F3 C8 C7 110.96(18) . . ?
F2 C8 C7 112.27(19) . . ?
F1 C8 C7 112.95(18) . . ?
C10 C9 C7 108.77(16) . . ?
C10 C9 C16 106.11(19) . . ?
C7 C9 C16 111.55(18) . . ?
C10 C9 C11 108.01(19) . . ?
C7 C9 C11 111.80(18) . . ?
C16 C9 C11 110.35(15) . . ?
N1 C10 C9 175.4(2) . . ?
C12 C11 C9 113.24(16) . . ?
C12 C11 H11A 108.9 . . ?
C9 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 O5 109.84(19) . . ?
C13 C12 C11 134.6(2) . . ?
O5 C12 C11 115.5(2) . . ?
C12 C13 C14 107.0(2) . . ?
C12 C13 H13 126.5 . . ?
C14 C13 H13 126.5 . . ?
C15 C14 C13 106.6(2) . . ?
C15 C14 H14 126.7 . . ?
C13 C14 H14 126.7 . . ?
C14 C15 O5 110.0(2) . . ?
C14 C15 H15 125 . . ?
O5 C15 H15 125 . . ?
O4 C16 O3 128.7(2) . . ?
O4 C16 C9 122.0(2) . . ?
O3 C16 C9 109.34(16) . . ?
O3 C17 C20 108.98(18) . . ?
O3 C17 C18 101.07(15) . . ?
C20 C17 C18 111.7(2) . . ?
O3 C17 C19 108.90(18) . . ?
C20 C17 C19 113.45(18) . . ?
C18 C17 C19 111.9(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 N2 C6 125.43(19) . . ?
O1 N3 O2 123.2(2) . . ?
O1 N3 C1 118.56(17) . . ?
O2 N3 C1 118.26(19) . . ?
C16 O3 C17 121.36(15) . . ?
C12 O5 C15 106.56(18) . . ?

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
C6 C1 C2 C3 0.0(3) . . . . ?
N3 C1 C2 C3 -179.4(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C3 C4 C5 C6 2.5(4) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 N2 -169.9(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N3 C1 C6 C5 179.5(2) . . . . ?
C2 C1 C6 N2 168.4(2) . . . . ?
N3 C1 C6 N2 -12.2(3) . . . . ?
N2 C7 C8 F3 -52.2(3) . . . . ?
C9 C7 C8 F3 128.2(2) . . . . ?
N2 C7 C8 F2 67.4(3) . . . . ?
C9 C7 C8 F2 -112.2(2) . . . . ?
N2 C7 C8 F1 -172.6(2) . . . . ?
C9 C7 C8 F1 7.7(3) . . . . ?
N2 C7 C9 C10 8.6(3) . . . . ?
C8 C7 C9 C10 -171.76(19) . . . . ?
N2 C7 C9 C16 125.3(2) . . . . ?
C8 C7 C9 C16 -55.1(3) . . . . ?
N2 C7 C9 C11 -110.6(2) . . . . ?
C8 C7 C9 C11 69.0(3) . . . . ?
C10 C9 C11 C12 -62.9(2) . . . . ?
C7 C9 C11 C12 56.7(3) . . . . ?
C16 C9 C11 C12 -178.53(19) . . . . ?
C9 C11 C12 C13 79.1(3) . . . . ?
C9 C11 C12 O5 -97.3(2) . . . . ?
O5 C12 C13 C14 -0.8(3) . . . . ?
C11 C12 C13 C14 -177.3(2) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 O5 -0.2(3) . . . . ?
C10 C9 C16 O4 -92.3(3) . . . . ?
C7 C9 C16 O4 149.4(2) . . . . ?
C11 C9 C16 O4 24.5(3) . . . . ?
C10 C9 C16 O3 87.1(2) . . . . ?
C7 C9 C16 O3 -31.2(3) . . . . ?
C11 C9 C16 O3 -156.13(19) . . . . ?
C8 C7 N2 C6 -6.7(4) . . . . ?
C9 C7 N2 C6 173.0(2) . . . . ?
C5 C6 N2 C7 -73.3(3) . . . . ?
C1 C6 N2 C7 118.5(3) . . . . ?
C2 C1 N3 O1 -18.7(3) . . . . ?
C6 C1 N3 O1 161.9(2) . . . . ?
C2 C1 N3 O2 160.71(19) . . . . ?
C6 C1 N3 O2 -18.8(3) . . . . ?
O4 C16 O3 C17 0.2(4) . . . . ?
C9 C16 O3 C17 -179.12(18) . . . . ?
C20 C17 O3 C16 -64.0(3) . . . . ?
C18 C17 O3 C16 178.2(2) . . . . ?
C19 C17 O3 C16 60.2(2) . . . . ?
C13 C12 O5 C15 0.7(2) . . . . ?
C11 C12 O5 C15 177.90(18) . . . . ?
C14 C15 O5 C12 -0.3(3) . . . . ?