# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       walther.schmid@univie.ac.at
_publ_contact_author_name        'Walther Schmid'
loop_
_publ_author_name
M.Fischer
H.Kaehlig
W.Schmid

data_mifi002
_database_code_depnum_ccdc_archive 'CCDC 809382'
#TrackingRef '- FHAP. CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;3-Fluoro-1-hydroxyacetone phosphate, bis-cyclohexylammonum
salt, monohydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H36 F N2 O7 P'
_chemical_formula_weight         406.43

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   6.4932(2)
_cell_length_b                   25.4590(7)
_cell_length_c                   12.3876(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5430(10)
_cell_angle_gamma                90.00
_cell_volume                     1998.92(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8972
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            58343
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         30.07
_reflns_number_total             5854
_reflns_number_gt                4967
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.0477P)^2^+0.8076P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5854
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_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
P1 P 0.20977(4) 0.228484(10) 0.82301(2) 0.00871(7) Uani 1 1 d . . .
F1 F -0.14070(12) 0.05384(3) 0.72905(6) 0.02197(16) Uani 1 1 d . . .
O1 O 0.43032(11) 0.22713(3) 0.79961(6) 0.01190(15) Uani 1 1 d . . .
O2 O 0.21035(11) 0.21881(3) 0.94448(6) 0.01224(15) Uani 1 1 d . . .
O3 O 0.09986(11) 0.17735(3) 0.75567(6) 0.01115(15) Uani 1 1 d . . .
O4 O 0.08032(11) 0.27630(3) 0.77746(7) 0.01242(15) Uani 1 1 d . . .
O5 O -0.12165(12) 0.15478(3) 0.93377(7) 0.01608(17) Uani 1 1 d . . .
H5 H -0.0112 0.1726 0.9383 0.024 Uiso 1 1 calc R . .
O6 O -0.40197(11) 0.12590(3) 0.80126(7) 0.01545(16) Uani 1 1 d . . .
H6 H -0.4626 0.1552 0.7968 0.023 Uiso 1 1 calc R . .
C1 C -0.12288(15) 0.16932(4) 0.73901(9) 0.01145(19) Uani 1 1 d . . .
H1A H -0.1756 0.1538 0.6648 0.014 Uiso 1 1 calc R . .
H1B H -0.1929 0.2038 0.7408 0.014 Uiso 1 1 calc R . .
C2 C -0.18329(15) 0.13334(4) 0.82592(9) 0.01186(19) Uani 1 1 d . . .
C3 C -0.08033(17) 0.07980(5) 0.83054(10) 0.0166(2) Uani 1 1 d . . .
H3A H 0.0750 0.0839 0.8493 0.020 Uiso 1 1 calc R . .
H3B H -0.1217 0.0585 0.8892 0.020 Uiso 1 1 calc R . .
O7 O 0.44946(13) 0.25728(4) 0.59297(7) 0.01811(17) Uani 1 1 d . . .
H71 H 0.460(3) 0.2440(8) 0.6586(18) 0.044(5) Uiso 1 1 d . . .
H72 H 0.563(3) 0.2591(8) 0.5767(16) 0.044(5) Uiso 1 1 d . . .
N1 N 0.76336(14) 0.29300(4) 0.89359(8) 0.01274(18) Uani 1 1 d . . .
H1C H 0.8702 0.2912 0.8569 0.019 Uiso 1 1 calc R . .
H1D H 0.6475 0.2764 0.8535 0.019 Uiso 1 1 calc R . .
H1E H 0.8039 0.2771 0.9607 0.019 Uiso 1 1 calc R . .
N2 N 0.07345(13) 0.32317(4) 0.57444(8) 0.01169(17) Uani 1 1 d . . .
H2A H -0.0455 0.3096 0.5307 0.018 Uiso 1 1 calc R . .
H2B H 0.0951 0.3081 0.6426 0.018 Uiso 1 1 calc R . .
H2C H 0.1859 0.3165 0.5437 0.018 Uiso 1 1 calc R . .
C10 C 0.71161(16) 0.34920(4) 0.90960(9) 0.01236(19) Uani 1 1 d . . .
H10 H 0.6650 0.3660 0.8354 0.015 Uiso 1 1 calc R . .
C11 C 0.53250(16) 0.35285(4) 0.97085(9) 0.0137(2) Uani 1 1 d . . .
H11A H 0.5719 0.3338 1.0420 0.016 Uiso 1 1 calc R . .
H11B H 0.4042 0.3362 0.9262 0.016 Uiso 1 1 calc R . .
C12 C 0.48675(17) 0.41037(5) 0.99237(10) 0.0159(2) Uani 1 1 d . . .
H12A H 0.4370 0.4287 0.9210 0.019 Uiso 1 1 calc R . .
H12B H 0.3733 0.4123 1.0343 0.019 Uiso 1 1 calc R . .
C13 C 0.68422(18) 0.43771(5) 1.05787(10) 0.0185(2) Uani 1 1 d . . .
H13A H 0.6521 0.4751 1.0692 0.022 Uiso 1 1 calc R . .
H13B H 0.7283 0.4210 1.1314 0.022 Uiso 1 1 calc R . .
C14 C 0.86361(18) 0.43418(5) 0.99637(12) 0.0217(2) Uani 1 1 d . . .
H14A H 0.9921 0.4505 1.0417 0.026 Uiso 1 1 calc R . .
H14B H 0.8247 0.4539 0.9260 0.026 Uiso 1 1 calc R . .
C15 C 0.90986(16) 0.37709(5) 0.97202(11) 0.0178(2) Uani 1 1 d . . .
H15A H 1.0191 0.3760 0.9273 0.021 Uiso 1 1 calc R . .
H15B H 0.9658 0.3585 1.0425 0.021 Uiso 1 1 calc R . .
C16 C 0.04856(16) 0.38107(4) 0.58480(9) 0.01180(19) Uani 1 1 d . . .
H16 H 0.0270 0.3972 0.5096 0.014 Uiso 1 1 calc R . .
C17 C -0.14363(16) 0.39249(5) 0.63245(10) 0.0153(2) Uani 1 1 d . . .
H17A H -0.1276 0.3750 0.7052 0.018 Uiso 1 1 calc R . .
H17B H -0.2714 0.3782 0.5826 0.018 Uiso 1 1 calc R . .
C18 C -0.16965(18) 0.45165(5) 0.64620(11) 0.0215(2) Uani 1 1 d . . .
H18A H -0.2020 0.4685 0.5724 0.026 Uiso 1 1 calc R . .
H18B H -0.2900 0.4581 0.6817 0.026 Uiso 1 1 calc R . .
C19 C 0.02933(18) 0.47644(5) 0.71638(11) 0.0201(2) Uani 1 1 d . . .
H19A H 0.0503 0.4634 0.7933 0.024 Uiso 1 1 calc R . .
H19B H 0.0115 0.5150 0.7177 0.024 Uiso 1 1 calc R . .
C20 C 0.22352(19) 0.46330(5) 0.67053(11) 0.0202(2) Uani 1 1 d . . .
H20A H 0.2110 0.4805 0.5977 0.024 Uiso 1 1 calc R . .
H20B H 0.3511 0.4773 0.7210 0.024 Uiso 1 1 calc R . .
C21 C 0.24768(16) 0.40407(5) 0.65768(10) 0.0160(2) Uani 1 1 d . . .
H21A H 0.3700 0.3969 0.6241 0.019 Uiso 1 1 calc R . .
H21B H 0.2744 0.3871 0.7313 0.019 Uiso 1 1 calc R . .

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
P1 0.00728(11) 0.01001(13) 0.00911(12) 0.00044(9) 0.00236(9) 0.00016(8)
F1 0.0283(4) 0.0149(3) 0.0248(4) -0.0042(3) 0.0104(3) 0.0005(3)
O1 0.0085(3) 0.0145(4) 0.0134(4) -0.0004(3) 0.0039(3) -0.0007(3)
O2 0.0111(3) 0.0164(4) 0.0095(3) 0.0007(3) 0.0028(3) -0.0004(3)
O3 0.0084(3) 0.0124(4) 0.0129(4) -0.0021(3) 0.0029(3) -0.0012(3)
O4 0.0123(3) 0.0114(4) 0.0140(4) 0.0023(3) 0.0041(3) 0.0024(3)
O5 0.0159(3) 0.0211(4) 0.0126(4) -0.0027(3) 0.0062(3) -0.0058(3)
O6 0.0096(3) 0.0143(4) 0.0230(4) -0.0013(3) 0.0047(3) -0.0011(3)
C1 0.0085(4) 0.0138(5) 0.0118(5) 0.0000(4) 0.0016(3) -0.0014(3)
C2 0.0100(4) 0.0127(5) 0.0133(5) -0.0007(4) 0.0033(3) -0.0012(3)
C3 0.0173(5) 0.0138(5) 0.0192(5) 0.0016(4) 0.0051(4) 0.0012(4)
O7 0.0144(4) 0.0259(5) 0.0155(4) 0.0051(3) 0.0064(3) 0.0030(3)
N1 0.0110(4) 0.0136(4) 0.0141(4) -0.0028(3) 0.0039(3) -0.0010(3)
N2 0.0101(3) 0.0131(4) 0.0121(4) -0.0013(3) 0.0028(3) 0.0009(3)
C10 0.0114(4) 0.0131(5) 0.0131(5) -0.0016(4) 0.0039(4) -0.0004(4)
C11 0.0120(4) 0.0151(5) 0.0150(5) -0.0024(4) 0.0052(4) -0.0013(4)
C12 0.0145(4) 0.0170(5) 0.0164(5) -0.0034(4) 0.0037(4) 0.0020(4)
C13 0.0185(5) 0.0168(5) 0.0194(6) -0.0058(4) 0.0022(4) 0.0002(4)
C14 0.0183(5) 0.0159(6) 0.0317(7) -0.0054(5) 0.0070(5) -0.0049(4)
C15 0.0115(4) 0.0170(5) 0.0249(6) -0.0054(4) 0.0043(4) -0.0030(4)
C16 0.0126(4) 0.0116(5) 0.0114(5) -0.0003(4) 0.0029(4) 0.0005(4)
C17 0.0106(4) 0.0156(5) 0.0199(5) -0.0042(4) 0.0040(4) 0.0000(4)
C18 0.0159(5) 0.0173(6) 0.0299(7) -0.0058(5) 0.0019(4) 0.0041(4)
C19 0.0183(5) 0.0157(5) 0.0266(6) -0.0069(5) 0.0055(4) -0.0004(4)
C20 0.0204(5) 0.0167(6) 0.0254(6) -0.0049(5) 0.0091(4) -0.0067(4)
C21 0.0111(4) 0.0183(5) 0.0194(5) -0.0058(4) 0.0048(4) -0.0029(4)

_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
P1 O4 1.5169(8) . ?
P1 O1 1.5219(7) . ?
P1 O2 1.5240(8) . ?
P1 O3 1.6253(8) . ?
F1 C3 1.3990(14) . ?
O3 C1 1.4305(11) . ?
O5 C2 1.4180(13) . ?
O5 H5 0.8400 . ?
O6 C2 1.3989(12) . ?
O6 H6 0.8400 . ?
C1 C2 1.5283(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5137(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O7 H71 0.87(2) . ?
O7 H72 0.80(2) . ?
N1 C10 1.4928(14) . ?
N1 H1C 0.9100 . ?
N1 H1D 0.9100 . ?
N1 H1E 0.9100 . ?
N2 C16 1.4915(14) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C10 C11 1.5232(14) . ?
C10 C15 1.5254(15) . ?
C10 H10 1.0000 . ?
C11 C12 1.5290(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5281(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5267(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5274(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5200(14) . ?
C16 C21 1.5240(14) . ?
C16 H16 1.0000 . ?
C17 C18 1.5291(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5282(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5283(16) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5281(17) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
O4 P1 O1 114.56(4) . . ?
O4 P1 O2 112.30(4) . . ?
O1 P1 O2 112.56(4) . . ?
O4 P1 O3 107.81(4) . . ?
O1 P1 O3 102.15(4) . . ?
O2 P1 O3 106.49(4) . . ?
C1 O3 P1 120.40(7) . . ?
C2 O5 H5 109.5 . . ?
C2 O6 H6 109.5 . . ?
O3 C1 C2 112.96(8) . . ?
O3 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
O3 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
O6 C2 O5 108.86(8) . . ?
O6 C2 C3 107.78(9) . . ?
O5 C2 C3 106.20(9) . . ?
O6 C2 C1 109.33(8) . . ?
O5 C2 C1 111.71(9) . . ?
C3 C2 C1 112.80(9) . . ?
F1 C3 C2 110.87(9) . . ?
F1 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
F1 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
H71 O7 H72 111.4(19) . . ?
C10 N1 H1C 109.5 . . ?
C10 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C10 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C16 N2 H2A 109.5 . . ?
C16 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C16 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N1 C10 C11 110.06(9) . . ?
N1 C10 C15 108.90(8) . . ?
C11 C10 C15 111.75(9) . . ?
N1 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C15 C10 H10 108.7 . . ?
C10 C11 C12 110.10(9) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 110.88(9) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 110.57(10) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.01(10) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C10 C15 C14 111.26(9) . . ?
C10 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C10 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N2 C16 C17 109.63(9) . . ?
N2 C16 C21 109.68(8) . . ?
C17 C16 C21 111.03(9) . . ?
N2 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C21 C16 H16 108.8 . . ?
C16 C17 C18 110.59(9) . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 111.70(9) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 111.23(10) . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C19 111.49(10) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C16 C21 C20 110.35(9) . . ?
C16 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C16 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?

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
O4 P1 O3 C1 -47.48(8) . . . . ?
O1 P1 O3 C1 -168.53(7) . . . . ?
O2 P1 O3 C1 73.23(8) . . . . ?
P1 O3 C1 C2 -95.24(9) . . . . ?
O3 C1 C2 O6 -177.69(8) . . . . ?
O3 C1 C2 O5 61.75(11) . . . . ?
O3 C1 C2 C3 -57.79(12) . . . . ?
O6 C2 C3 F1 60.22(11) . . . . ?
O5 C2 C3 F1 176.75(8) . . . . ?
C1 C2 C3 F1 -60.57(11) . . . . ?
N1 C10 C11 C12 177.19(8) . . . . ?
C15 C10 C11 C12 56.06(12) . . . . ?
C10 C11 C12 C13 -57.34(12) . . . . ?
C11 C12 C13 C14 57.75(13) . . . . ?
C12 C13 C14 C15 -56.22(14) . . . . ?
N1 C10 C15 C14 -176.92(10) . . . . ?
C11 C10 C15 C14 -55.12(13) . . . . ?
C13 C14 C15 C10 54.84(14) . . . . ?
N2 C16 C17 C18 178.77(9) . . . . ?
C21 C16 C17 C18 57.42(12) . . . . ?
C16 C17 C18 C19 -55.39(14) . . . . ?
C17 C18 C19 C20 53.85(15) . . . . ?
C18 C19 C20 C21 -54.30(14) . . . . ?
N2 C16 C21 C20 -179.18(9) . . . . ?
C17 C16 C21 C20 -57.85(12) . . . . ?
C19 C20 C21 C16 56.19(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.07
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.052