# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_global

data_tc03196

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26.50 F3 N3 O5.25'
_chemical_formula_weight         449.94

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P22121

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

_cell_length_a                   6.4489(2)
_cell_length_b                   9.7481(3)
_cell_length_c                   36.0860(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2268.53(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             946
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 19.64
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30023
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4949
_reflns_number_gt                3033
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'

_computing_structure_solution    'SIR-97_(Altomare & al., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON_(Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0470P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0021(7)
_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   0.4(8)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4949
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_restrained_S_all      0.829
_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 0.2565(2) 0.27526(16) 0.77124(4) 0.0241(4) Uani 1 1 d . . .
H1 H 0.2898 0.2246 0.7905 0.029 Uiso 1 1 calc R . .
C5 C 0.2539(4) 0.3192(2) 0.67139(5) 0.0345(5) Uani 1 1 d . . .
H5A H 0.2929 0.2211 0.6699 0.041 Uiso 1 1 calc R . .
H5B H 0.1147 0.3309 0.6603 0.041 Uiso 1 1 calc R . .
N3 N 0.3203(3) 0.36298(19) 0.58519(4) 0.0373(5) Uani 1 1 d . . .
H3A H 0.2220 0.2991 0.5918 0.045 Uiso 1 1 calc R . .
H3B H 0.4452 0.3184 0.5826 0.045 Uiso 1 1 calc R . .
O1 O 0.5207(2) 0.20577(13) 0.73338(4) 0.0271(3) Uani 1 1 d . . .
O2 O -0.0771(2) 0.27222(16) 0.71535(4) 0.0359(4) Uani 1 1 d . . .
H2A H -0.1997 0.2701 0.7256 0.050 Uiso 1 1 d . . .
O3 O 0.5692(2) 0.62161(16) 0.67048(4) 0.0402(4) Uani 1 1 d . . .
C1 C 0.3606(3) 0.2718(2) 0.73977(5) 0.0223(5) Uani 1 1 d . . .
C2 C 0.0804(3) 0.3708(2) 0.77136(5) 0.0224(4) Uani 1 1 d . . .
H2B H 0.1295 0.4615 0.7808 0.027 Uiso 1 1 calc R . .
C3 C 0.0373(3) 0.3843(2) 0.72964(5) 0.0257(5) Uani 1 1 d . . .
H3 H -0.0275 0.4744 0.7233 0.031 Uiso 1 1 calc R . .
C4 C 0.2534(3) 0.36777(19) 0.71218(5) 0.0237(4) Uani 1 1 d . . .
N2 N 0.3709(2) 0.49647(17) 0.71059(4) 0.0250(4) Uani 1 1 d . . .
H2 H 0.3816 0.5525 0.7296 0.030 Uiso 1 1 calc R . .
C6 C 0.4605(3) 0.5218(2) 0.67783(5) 0.0268(5) Uani 1 1 d . . .
C7 C 0.4113(3) 0.4068(2) 0.65120(5) 0.0258(5) Uani 1 1 d . . .
H7 H 0.5396 0.3517 0.6467 0.031 Uiso 1 1 calc R . .
C8 C 0.3379(4) 0.4684(2) 0.61486(6) 0.0405(6) Uani 1 1 d . . .
H8A H 0.2011 0.5123 0.6186 0.049 Uiso 1 1 calc R . .
H8B H 0.4368 0.5403 0.6069 0.049 Uiso 1 1 calc R . .
C9 C 0.2609(6) 0.4272(3) 0.54927(6) 0.0602(8) Uani 1 1 d . . .
H9A H 0.3660 0.4968 0.5425 0.072 Uiso 1 1 calc R . .
H9B H 0.1262 0.4747 0.5523 0.072 Uiso 1 1 calc R . .
C10 C 0.2433(5) 0.3235(3) 0.51831(6) 0.0551(7) Uani 1 1 d . . .
C11 C 0.0552(6) 0.2907(4) 0.50448(8) 0.0859(11) Uani 1 1 d . . .
H11 H -0.0655 0.3296 0.5153 0.103 Uiso 1 1 calc R . .
C12 C 0.0340(7) 0.2012(5) 0.47477(10) 0.1095(15) Uani 1 1 d . . .
H12 H -0.0992 0.1822 0.4648 0.131 Uiso 1 1 calc R . .
C13 C 0.2028(7) 0.1420(4) 0.46033(9) 0.0942(12) Uani 1 1 d . . .
H13 H 0.1885 0.0784 0.4406 0.113 Uiso 1 1 calc R . .
C14 C 0.3907(6) 0.1714(4) 0.47341(10) 0.1031(14) Uani 1 1 d . . .
H14 H 0.5098 0.1303 0.4626 0.124 Uiso 1 1 calc R . .
C15 C 0.4130(6) 0.2640(4) 0.50341(8) 0.0894(11) Uani 1 1 d . . .
H15 H 0.5468 0.2841 0.5130 0.107 Uiso 1 1 calc R . .
C16 C -0.1017(3) 0.3241(2) 0.79500(5) 0.0274(5) Uani 1 1 d . . .
H16 H -0.1619 0.2397 0.7835 0.033 Uiso 1 1 calc R . .
C17 C -0.0388(4) 0.2898(3) 0.83457(6) 0.0520(7) Uani 1 1 d . . .
H17A H 0.0672 0.2177 0.8343 0.078 Uiso 1 1 calc R . .
H17B H -0.1603 0.2575 0.8483 0.078 Uiso 1 1 calc R . .
H17C H 0.0173 0.3720 0.8466 0.078 Uiso 1 1 calc R . .
C18 C -0.2653(4) 0.4341(2) 0.79488(6) 0.0395(6) Uani 1 1 d . . .
H18A H -0.3024 0.4566 0.7693 0.059 Uiso 1 1 calc R . .
H18B H -0.2116 0.5162 0.8073 0.059 Uiso 1 1 calc R . .
H18C H -0.3885 0.4011 0.8081 0.059 Uiso 1 1 calc R . .
C19 C 0.8331(4) 0.1923(3) 0.59571(6) 0.0376(6) Uani 1 1 d . . .
C20 C 0.6925(4) 0.0717(3) 0.60764(8) 0.0512(7) Uani 1 1 d . . .
F2 F 0.7614(2) -0.04870(14) 0.59532(4) 0.0587(4) Uani 1 1 d . . .
F1 F 0.4977(3) 0.08328(17) 0.59728(6) 0.0946(7) Uani 1 1 d . . .
F3 F 0.6895(3) 0.06153(18) 0.64480(4) 0.0833(6) Uani 1 1 d . . .
O4 O 0.7390(3) 0.29567(17) 0.58414(4) 0.0487(4) Uani 1 1 d . . .
O5 O 1.0188(3) 0.17268(17) 0.59990(4) 0.0487(5) Uani 1 1 d . . .
O6 O -0.1495(9) 0.5620(6) 0.59964(16) 0.0351(14) Uiso 0.25 1 d P . .
H6A H -0.0823 0.5285 0.6178 0.050 Uiso 0.25 1 d P . .
H6B H -0.2701 0.5486 0.6059 0.050 Uiso 0.25 1 d P . .

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 0.0212(8) 0.0273(10) 0.0237(8) 0.0050(7) 0.0003(8) 0.0053(8)
C5 0.0402(13) 0.0383(13) 0.0249(11) -0.0046(10) 0.0003(11) -0.0133(12)
N3 0.0527(12) 0.0367(11) 0.0225(9) -0.0004(8) -0.0046(9) 0.0072(10)
O1 0.0184(7) 0.0270(8) 0.0358(8) -0.0042(7) 0.0019(6) -0.0009(7)
O2 0.0236(8) 0.0484(10) 0.0357(8) -0.0091(7) 0.0009(7) -0.0139(7)
O3 0.0491(10) 0.0385(9) 0.0328(8) 0.0008(7) 0.0039(8) -0.0233(9)
C1 0.0180(10) 0.0202(11) 0.0287(12) -0.0044(9) -0.0025(9) -0.0077(9)
C2 0.0198(10) 0.0193(10) 0.0282(11) -0.0029(9) -0.0019(10) -0.0001(9)
C3 0.0185(11) 0.0244(11) 0.0342(11) 0.0018(10) -0.0047(10) -0.0028(9)
C4 0.0263(11) 0.0205(10) 0.0243(10) 0.0006(8) -0.0047(10) -0.0045(10)
N2 0.0279(9) 0.0230(9) 0.0241(9) -0.0039(8) -0.0008(8) -0.0061(8)
C6 0.0265(12) 0.0287(12) 0.0252(12) 0.0018(9) -0.0009(10) -0.0032(10)
C7 0.0284(11) 0.0248(12) 0.0242(11) -0.0021(9) 0.0005(10) 0.0009(9)
C8 0.0608(16) 0.0349(14) 0.0258(12) -0.0026(10) -0.0039(11) 0.0021(12)
C9 0.104(2) 0.0535(16) 0.0231(13) 0.0032(12) -0.0100(16) 0.0179(18)
C10 0.082(2) 0.0595(18) 0.0239(13) 0.0018(11) -0.0070(15) 0.0099(18)
C11 0.089(2) 0.122(3) 0.0463(17) -0.0210(19) 0.0096(19) -0.025(2)
C12 0.103(3) 0.157(4) 0.069(2) -0.045(3) 0.009(2) -0.048(3)
C13 0.117(3) 0.110(3) 0.055(2) -0.027(2) -0.007(2) -0.011(3)
C14 0.100(3) 0.132(4) 0.077(2) -0.052(3) -0.013(2) 0.035(3)
C15 0.090(2) 0.119(3) 0.0593(19) -0.032(2) -0.024(2) 0.033(3)
C16 0.0243(11) 0.0265(11) 0.0314(12) -0.0034(9) 0.0002(10) 0.0015(9)
C17 0.0348(14) 0.085(2) 0.0358(13) 0.0077(14) 0.0034(11) -0.0026(14)
C18 0.0275(12) 0.0333(13) 0.0577(15) -0.0082(12) 0.0053(13) 0.0054(11)
C19 0.0425(15) 0.0404(15) 0.0299(13) -0.0077(11) -0.0005(11) 0.0035(12)
C20 0.0523(18) 0.0410(16) 0.0603(19) -0.0028(14) -0.0089(15) 0.0063(14)
F2 0.0707(10) 0.0371(9) 0.0683(9) -0.0117(7) -0.0082(9) 0.0075(8)
F1 0.0457(10) 0.0552(11) 0.183(2) 0.0212(12) -0.0233(12) -0.0033(9)
F3 0.1200(15) 0.0672(12) 0.0627(11) 0.0015(9) 0.0315(11) -0.0052(11)
O4 0.0542(11) 0.0468(11) 0.0451(9) 0.0018(9) 0.0089(9) 0.0068(10)
O5 0.0405(10) 0.0562(12) 0.0492(10) -0.0079(8) -0.0065(8) -0.0040(9)

_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 1.320(2) . ?
N1 C2 1.468(2) . ?
N1 H1 0.8800 . ?
C5 C7 1.514(3) . ?
C5 C4 1.546(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N3 C8 1.488(3) . ?
N3 C9 1.490(3) . ?
N3 H3A 0.9200 . ?
N3 H3B 0.9200 . ?
O1 C1 1.239(2) . ?
O2 C3 1.415(2) . ?
O2 H2A 0.8728 . ?
O3 C6 1.228(2) . ?
C1 C4 1.531(3) . ?
C2 C16 1.521(3) . ?
C2 C3 1.537(3) . ?
C2 H2B 1.0000 . ?
C3 C4 1.538(3) . ?
C3 H3 1.0000 . ?
C4 N2 1.467(2) . ?
N2 C6 1.339(2) . ?
N2 H2 0.8800 . ?
C6 C7 1.510(3) . ?
C7 C8 1.518(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.510(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.350(4) . ?
C10 C15 1.351(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.338(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.331(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C18 1.505(3) . ?
C16 C17 1.522(3) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O5 1.222(3) . ?
C19 O4 1.248(3) . ?
C19 C20 1.546(4) . ?
C20 F1 1.315(3) . ?
C20 F2 1.331(3) . ?
C20 F3 1.345(3) . ?
O6 H6A 0.8509 . ?
O6 H6B 0.8202 . ?

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 C2 114.33(15) . . ?
C1 N1 H1 122.8 . . ?
C2 N1 H1 122.8 . . ?
C7 C5 C4 106.66(16) . . ?
C7 C5 H5A 110.4 . . ?
C4 C5 H5A 110.4 . . ?
C7 C5 H5B 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C8 N3 C9 110.85(17) . . ?
C8 N3 H3A 109.5 . . ?
C9 N3 H3A 109.5 . . ?
C8 N3 H3B 109.5 . . ?
C9 N3 H3B 109.5 . . ?
H3A N3 H3B 108.1 . . ?
C3 O2 H2A 109.6 . . ?
O1 C1 N1 126.69(18) . . ?
O1 C1 C4 124.96(18) . . ?
N1 C1 C4 108.33(17) . . ?
N1 C2 C16 114.13(16) . . ?
N1 C2 C3 101.04(15) . . ?
C16 C2 C3 115.80(16) . . ?
N1 C2 H2B 108.5 . . ?
C16 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
O2 C3 C2 112.66(16) . . ?
O2 C3 C4 104.04(15) . . ?
C2 C3 C4 103.18(15) . . ?
O2 C3 H3 112.1 . . ?
C2 C3 H3 112.1 . . ?
C4 C3 H3 112.1 . . ?
N2 C4 C1 108.36(15) . . ?
N2 C4 C3 113.25(16) . . ?
C1 C4 C3 101.93(15) . . ?
N2 C4 C5 102.92(15) . . ?
C1 C4 C5 115.53(17) . . ?
C3 C4 C5 115.07(17) . . ?
C6 N2 C4 114.53(16) . . ?
C6 N2 H2 122.7 . . ?
C4 N2 H2 122.7 . . ?
O3 C6 N2 125.66(19) . . ?
O3 C6 C7 124.78(18) . . ?
N2 C6 C7 109.54(17) . . ?
C5 C7 C6 104.68(16) . . ?
C5 C7 C8 115.46(18) . . ?
C6 C7 C8 108.79(17) . . ?
C5 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
N3 C8 C7 111.89(17) . . ?
N3 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N3 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N3 C9 C10 112.5(2) . . ?
N3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 118.6(3) . . ?
C11 C10 C9 120.0(3) . . ?
C15 C10 C9 121.4(3) . . ?
C10 C11 C12 121.5(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 119.7(3) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C18 C16 C17 110.25(18) . . ?
C18 C16 C2 109.06(17) . . ?
C17 C16 C2 112.72(17) . . ?
C18 C16 H16 108.2 . . ?
C17 C16 H16 108.2 . . ?
C2 C16 H16 108.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 O4 130.1(2) . . ?
O5 C19 C20 114.9(2) . . ?
O4 C19 C20 115.0(2) . . ?
F1 C20 F2 107.4(2) . . ?
F1 C20 F3 106.0(2) . . ?
F2 C20 F3 105.8(2) . . ?
F1 C20 C19 114.6(2) . . ?
F2 C20 C19 112.4(2) . . ?
F3 C20 C19 110.0(2) . . ?
H6A O6 H6B 102.1 . . ?

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
C2 N1 C1 O1 175.81(17) . . . . ?
C2 N1 C1 C4 -2.5(2) . . . . ?
C1 N1 C2 C16 147.24(17) . . . . ?
C1 N1 C2 C3 22.3(2) . . . . ?
N1 C2 C3 O2 79.75(18) . . . . ?
C16 C2 C3 O2 -44.1(2) . . . . ?
N1 C2 C3 C4 -31.83(18) . . . . ?
C16 C2 C3 C4 -155.67(16) . . . . ?
O1 C1 C4 N2 -77.1(2) . . . . ?
N1 C1 C4 N2 101.24(18) . . . . ?
O1 C1 C4 C3 163.23(17) . . . . ?
N1 C1 C4 C3 -18.43(19) . . . . ?
O1 C1 C4 C5 37.7(3) . . . . ?
N1 C1 C4 C5 -143.95(17) . . . . ?
O2 C3 C4 N2 156.81(15) . . . . ?
C2 C3 C4 N2 -85.39(19) . . . . ?
O2 C3 C4 C1 -87.02(16) . . . . ?
C2 C3 C4 C1 30.79(18) . . . . ?
O2 C3 C4 C5 38.8(2) . . . . ?
C2 C3 C4 C5 156.61(17) . . . . ?
C7 C5 C4 N2 12.3(2) . . . . ?
C7 C5 C4 C1 -105.5(2) . . . . ?
C7 C5 C4 C3 136.01(18) . . . . ?
C1 C4 N2 C6 114.74(18) . . . . ?
C3 C4 N2 C6 -132.95(17) . . . . ?
C5 C4 N2 C6 -8.1(2) . . . . ?
C4 N2 C6 O3 -178.44(19) . . . . ?
C4 N2 C6 C7 0.4(2) . . . . ?
C4 C5 C7 C6 -12.3(2) . . . . ?
C4 C5 C7 C8 -131.91(19) . . . . ?
O3 C6 C7 C5 -173.4(2) . . . . ?
N2 C6 C7 C5 7.8(2) . . . . ?
O3 C6 C7 C8 -49.5(3) . . . . ?
N2 C6 C7 C8 131.71(18) . . . . ?
C9 N3 C8 C7 -176.5(2) . . . . ?
C5 C7 C8 N3 -72.3(2) . . . . ?
C6 C7 C8 N3 170.43(18) . . . . ?
C8 N3 C9 C10 179.5(2) . . . . ?
N3 C9 C10 C11 109.1(3) . . . . ?
N3 C9 C10 C15 -72.2(4) . . . . ?
C15 C10 C11 C12 -2.1(5) . . . . ?
C9 C10 C11 C12 176.6(3) . . . . ?
C10 C11 C12 C13 2.6(6) . . . . ?
C11 C12 C13 C14 -2.1(7) . . . . ?
C12 C13 C14 C15 1.3(7) . . . . ?
C11 C10 C15 C14 1.3(5) . . . . ?
C9 C10 C15 C14 -177.5(3) . . . . ?
C13 C14 C15 C10 -0.9(6) . . . . ?
N1 C2 C16 C18 176.31(16) . . . . ?
C3 C2 C16 C18 -67.0(2) . . . . ?
N1 C2 C16 C17 53.5(2) . . . . ?
C3 C2 C16 C17 170.23(19) . . . . ?
O5 C19 C20 F1 -168.8(2) . . . . ?
O4 C19 C20 F1 12.8(3) . . . . ?
O5 C19 C20 F2 -45.8(3) . . . . ?
O4 C19 C20 F2 135.8(2) . . . . ?
O5 C19 C20 F3 71.9(3) . . . . ?
O4 C19 C20 F3 -106.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038


_database_code_depnum_ccdc_archive 'CCDC 751234'