# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ISV-606
_database_code_depnum_ccdc_archive 'CCDC 1025516'
_audit_update_record             
;
2014-09-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 F N2 O5 P'
_chemical_formula_sum            'C14 H22 F N2 O5 P'
_chemical_formula_weight         348.31
_chemical_absolute_configuration ad

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   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   7.710(2)
_cell_length_b                   12.999(4)
_cell_length_c                   17.692(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.506(8)
_cell_angle_gamma                90.00
_cell_volume                     1771.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6095
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      21.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;


_diffrn_ambient_temperature      213(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  
;
  Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24983
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_sigmaI/netI    0.0924
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6290
_reflns_number_gt                3669
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² 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/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_number_reflns         6290
_refine_ls_number_parameters     0
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.2394
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.005
_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 0.5887(4) 0.1446(2) 0.6049(2) 0.0366(8) Uani 1 1 d . . .
F1 F 0.7239(12) 0.4220(6) 0.5983(5) 0.060(2) Uani 1 1 d . . .
O1 O 0.9217(9) 0.1199(6) 0.6116(5) 0.0354(18) Uani 1 1 d . . .
H1 H 0.9035 0.0776 0.6454 0.053 Uiso 1 1 calc R . .
O2 O 0.8751(14) 0.3955(9) 0.7950(6) 0.063(2) Uani 1 1 d . . .
O3 O 0.5447(11) 0.0795(7) 0.6687(6) 0.048(2) Uani 1 1 d . . .
O4 O 0.5784(10) 0.0874(7) 0.5273(5) 0.0391(15) Uani 1 1 d . . .
O5 O 0.4659(10) 0.2394(6) 0.5871(5) 0.0399(16) Uani 1 1 d . . .
N1 N 0.9862(13) 0.3183(9) 0.6947(6) 0.0422(18) Uani 1 1 d . . .
N2 N 0.9894(15) 0.3814(9) 0.7476(7) 0.0487(18) Uani 1 1 d . . .
C1 C 0.7990(14) 0.2019(10) 0.6147(8) 0.0378(15) Uani 1 1 d . . .
C2 C 0.8375(16) 0.2695(10) 0.5446(8) 0.0400(15) Uani 1 1 d . . .
C3 C 0.8010(18) 0.3755(11) 0.5398(9) 0.0473(18) Uani 1 1 d . . .
C4 C 0.8281(18) 0.4338(12) 0.4803(9) 0.053(2) Uani 1 1 d . . .
H4 H 0.7991 0.5040 0.4795 0.064 Uiso 1 1 calc R . .
C5 C 0.9039(19) 0.3850(12) 0.4166(9) 0.053(2) Uani 1 1 d . . .
H5 H 0.9276 0.4227 0.3729 0.064 Uiso 1 1 calc R . .
C6 C 0.9401(18) 0.2839(12) 0.4214(9) 0.051(2) Uani 1 1 d . . .
H6 H 0.9893 0.2518 0.3799 0.061 Uiso 1 1 calc R . .
C7 C 0.9094(15) 0.2258(11) 0.4833(8) 0.0436(18) Uani 1 1 d . . .
H7 H 0.9376 0.1554 0.4838 0.052 Uiso 1 1 calc R . .
C8 C 0.8171(15) 0.2593(10) 0.6914(8) 0.0398(17) Uani 1 1 d . . .
H8A H 0.7195 0.3068 0.6962 0.048 Uiso 1 1 calc R . .
H8B H 0.8158 0.2098 0.7331 0.048 Uiso 1 1 calc R . .
C9 C 1.1458(19) 0.4478(12) 0.7514(9) 0.053(2) Uani 1 1 d . . .
C10 C 1.154(2) 0.5109(12) 0.8265(10) 0.063(3) Uani 1 1 d . . .
H10A H 1.0369 0.5232 0.8425 0.094 Uiso 1 1 calc R . .
H10B H 1.2109 0.5762 0.8183 0.094 Uiso 1 1 calc R . .
H10C H 1.2186 0.4726 0.8654 0.094 Uiso 1 1 calc R . .
C11 C 1.132(2) 0.5227(13) 0.6840(10) 0.067(3) Uani 1 1 d . . .
H11A H 1.0215 0.5129 0.6566 0.101 Uiso 1 1 calc R . .
H11B H 1.2258 0.5095 0.6505 0.101 Uiso 1 1 calc R . .
H11C H 1.1401 0.5929 0.7025 0.101 Uiso 1 1 calc R . .
C12 C 1.3153(19) 0.3840(13) 0.7481(10) 0.060(3) Uani 1 1 d . . .
H12A H 1.2968 0.3268 0.7135 0.090 Uiso 1 1 calc R . .
H12B H 1.3474 0.3580 0.7981 0.090 Uiso 1 1 calc R . .
H12C H 1.4077 0.4274 0.7305 0.090 Uiso 1 1 calc R . .
C13 C 0.6356(19) -0.0194(12) 0.5200(9) 0.054(3) Uani 1 1 d . . .
H13A H 0.7543 -0.0206 0.5039 0.081 Uiso 1 1 calc R . .
H13B H 0.5608 -0.0545 0.4828 0.081 Uiso 1 1 calc R . .
H13C H 0.6296 -0.0538 0.5685 0.081 Uiso 1 1 calc R . .
C14 C 0.2882(15) 0.2271(13) 0.5676(9) 0.052(3) Uani 1 1 d . . .
H14A H 0.2748 0.1988 0.5169 0.078 Uiso 1 1 calc R . .
H14B H 0.2306 0.2933 0.5692 0.078 Uiso 1 1 calc R . .
H14C H 0.2367 0.1806 0.6031 0.078 Uiso 1 1 calc R . .
P2 P 0.9307(4) 0.9581(3) 0.8111(2) 0.0446(9) Uani 1 1 d . . .
F2 F 0.7924(13) 0.6968(7) 0.8715(6) 0.071(2) Uani 1 1 d . . .
O6 O 0.5935(11) 0.9929(7) 0.8166(5) 0.046(2) Uani 1 1 d . . .
H6A H 0.5925 1.0104 0.7715 0.068 Uiso 1 1 calc R . .
O7 O 0.6588(16) 0.8313(11) 1.0501(7) 0.079(3) Uani 1 1 d . . .
O8 O 0.9359(12) 1.0031(8) 0.7353(6) 0.050(2) Uani 1 1 d . . .
O9 O 1.0478(12) 0.8603(8) 0.8248(6) 0.0558(18) Uani 1 1 d . . .
O10 O 0.9731(13) 1.0400(8) 0.8770(6) 0.0550(18) Uani 1 1 d . . .
N3 N 0.5383(15) 0.8435(11) 0.9326(7) 0.055(2) Uani 1 1 d . . .
N4 N 0.5350(17) 0.8199(11) 1.0005(8) 0.062(2) Uani 1 1 d . . .
C15 C 0.7154(17) 0.9118(12) 0.8293(8) 0.0465(16) Uani 1 1 d . . .
C16 C 0.6732(17) 0.8150(11) 0.7802(9) 0.0476(16) Uani 1 1 d . . .
C17 C 0.7149(19) 0.7166(12) 0.8060(10) 0.0552(19) Uani 1 1 d . . .
C18 C 0.6803(19) 0.6342(13) 0.7571(10) 0.058(2) Uani 1 1 d . . .
H18 H 0.7119 0.5674 0.7728 0.070 Uiso 1 1 calc R . .
C19 C 0.6030(18) 0.6474(13) 0.6880(9) 0.054(2) Uani 1 1 d . . .
H19 H 0.5800 0.5907 0.6562 0.065 Uiso 1 1 calc R . .
C20 C 0.5594(18) 0.7426(11) 0.6653(9) 0.052(2) Uani 1 1 d . . .
H20 H 0.5039 0.7523 0.6175 0.062 Uiso 1 1 calc R . .
C21 C 0.5952(17) 0.8276(12) 0.7118(8) 0.0481(19) Uani 1 1 d . . .
H21 H 0.5643 0.8940 0.6949 0.058 Uiso 1 1 calc R . .
C22 C 0.7029(17) 0.8920(13) 0.9182(8) 0.0509(18) Uani 1 1 d . . .
H22A H 0.7986 0.8476 0.9363 0.061 Uiso 1 1 calc R . .
H22B H 0.7124 0.9575 0.9455 0.061 Uiso 1 1 calc R . .
C23 C 0.374(2) 0.7666(14) 1.0278(9) 0.064(2) Uani 1 1 d . . .
C24 C 0.392(2) 0.7321(16) 1.1055(9) 0.067(3) Uani 1 1 d . . .
H24A H 0.2910 0.6914 1.1174 0.100 Uiso 1 1 calc R . .
H24B H 0.4001 0.7913 1.1389 0.100 Uiso 1 1 calc R . .
H24C H 0.4956 0.6905 1.1123 0.100 Uiso 1 1 calc R . .
C25 C 0.315(3) 0.6883(17) 0.9713(10) 0.081(4) Uani 1 1 d . . .
H25A H 0.3977 0.6321 0.9713 0.122 Uiso 1 1 calc R . .
H25B H 0.3063 0.7194 0.9214 0.122 Uiso 1 1 calc R . .
H25C H 0.2021 0.6622 0.9842 0.122 Uiso 1 1 calc R . .
C26 C 0.223(2) 0.8613(16) 1.0270(11) 0.073(3) Uani 1 1 d . . .
H26A H 0.1134 0.8334 1.0422 0.110 Uiso 1 1 calc R . .
H26B H 0.2089 0.8895 0.9763 0.110 Uiso 1 1 calc R . .
H26C H 0.2608 0.9152 1.0619 0.110 Uiso 1 1 calc R . .
C27 C 1.2134(19) 0.8434(14) 0.7908(10) 0.063(3) Uani 1 1 d . . .
H27A H 1.2146 0.8791 0.7427 0.095 Uiso 1 1 calc R . .
H27B H 1.2300 0.7703 0.7828 0.095 Uiso 1 1 calc R . .
H27C H 1.3062 0.8695 0.8243 0.095 Uiso 1 1 calc R . .
C28 C 1.133(2) 1.1037(13) 0.8771(10) 0.068(4) Uani 1 1 d . . .
H28A H 1.2061 1.0806 0.8372 0.103 Uiso 1 1 calc R . .
H28B H 1.1961 1.0970 0.9256 0.103 Uiso 1 1 calc R . .
H28C H 1.1020 1.1752 0.8687 0.103 Uiso 1 1 calc R . .


_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 O3 1.462(10) . ?
P1 O4 1.560(9) . ?
P1 O5 1.577(9) . ?
P1 C1 1.786(12) . ?
F1 C3 1.357(17) . ?
O1 C1 1.427(14) . ?
O1 H1 0.8300 . ?
O2 N2 1.256(15) . ?
O4 C13 1.464(17) . ?
O5 C14 1.408(14) . ?
N1 N2 1.243(15) . ?
N1 C8 1.512(15) . ?
N2 C9 1.482(18) . ?
C1 C8 1.548(18) . ?
C1 C2 1.559(19) . ?
C2 C7 1.364(19) . ?
C2 C3 1.408(19) . ?
C3 C4 1.32(2) . ?
C4 C5 1.44(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.35(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.36(2) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C11 1.54(2) . ?
C9 C12 1.55(2) . ?
C9 C10 1.56(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
P2 O8 1.465(10) . ?
P2 O9 1.572(10) . ?
P2 O10 1.603(11) . ?
P2 C15 1.808(14) . ?
F2 C17 1.305(18) . ?
O6 C15 1.424(17) . ?
O6 H6A 0.8300 . ?
O7 N4 1.277(17) . ?
O9 C27 1.451(17) . ?
O10 C28 1.487(17) . ?
N3 N4 1.241(16) . ?
N3 C22 1.450(17) . ?
N4 C23 1.519(19) . ?
C15 C16 1.56(2) . ?
C15 C22 1.60(2) . ?
C16 C21 1.34(2) . ?
C16 C17 1.39(2) . ?
C17 C18 1.40(2) . ?
C18 C19 1.35(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.34(2) . ?
C19 H19 0.9400 . ?
C20 C21 1.40(2) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.45(2) . ?
C23 C25 1.48(2) . ?
C23 C26 1.69(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?

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
O3 P1 O4 113.5(5) . . ?
O3 P1 O5 116.7(5) . . ?
O4 P1 O5 101.0(5) . . ?
O3 P1 C1 114.0(6) . . ?
O4 P1 C1 107.2(5) . . ?
O5 P1 C1 103.2(5) . . ?
C1 O1 H1 109.5 . . ?
C13 O4 P1 121.7(9) . . ?
C14 O5 P1 121.9(9) . . ?
N2 N1 C8 110.7(10) . . ?
N1 N2 O2 127.4(11) . . ?
N1 N2 C9 114.1(11) . . ?
O2 N2 C9 118.5(12) . . ?
O1 C1 C8 111.1(9) . . ?
O1 C1 C2 103.9(9) . . ?
C8 C1 C2 114.3(10) . . ?
O1 C1 P1 106.6(8) . . ?
C8 C1 P1 109.4(8) . . ?
C2 C1 P1 111.1(8) . . ?
C7 C2 C3 116.5(13) . . ?
C7 C2 C1 119.7(12) . . ?
C3 C2 C1 123.7(13) . . ?
C4 C3 F1 116.2(13) . . ?
C4 C3 C2 124.8(15) . . ?
F1 C3 C2 118.9(13) . . ?
C3 C4 C5 117.1(14) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C6 C5 C4 118.1(15) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C7 123.4(16) . . ?
C5 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
C6 C7 C2 120.0(13) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N1 C8 C1 108.9(10) . . ?
N1 C8 H8A 109.9 . . ?
C1 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C1 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C11 107.7(12) . . ?
N2 C9 C12 111.9(12) . . ?
C11 C9 C12 109.8(13) . . ?
N2 C9 C10 110.3(12) . . ?
C11 C9 C10 109.0(13) . . ?
C12 C9 C10 108.1(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O8 P2 O9 115.2(6) . . ?
O8 P2 O10 112.8(6) . . ?
O9 P2 O10 109.1(6) . . ?
O8 P2 C15 111.0(6) . . ?
O9 P2 C15 103.2(6) . . ?
O10 P2 C15 104.5(6) . . ?
C15 O6 H6A 109.5 . . ?
C27 O9 P2 124.6(10) . . ?
C28 O10 P2 120.9(9) . . ?
N4 N3 C22 109.4(12) . . ?
N3 N4 O7 126.2(13) . . ?
N3 N4 C23 118.2(13) . . ?
O7 N4 C23 115.5(13) . . ?
O6 C15 C16 113.0(11) . . ?
O6 C15 C22 101.9(11) . . ?
C16 C15 C22 113.5(12) . . ?
O6 C15 P2 109.3(9) . . ?
C16 C15 P2 109.9(9) . . ?
C22 C15 P2 108.9(9) . . ?
C21 C16 C17 119.9(14) . . ?
C21 C16 C15 118.7(13) . . ?
C17 C16 C15 121.4(13) . . ?
F2 C17 C16 124.3(15) . . ?
F2 C17 C18 117.8(14) . . ?
C16 C17 C18 117.8(15) . . ?
C19 C18 C17 122.0(16) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C20 C19 C18 119.0(16) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 120.9(16) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C16 C21 C20 120.3(15) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
N3 C22 C15 109.4(11) . . ?
N3 C22 H22A 109.8 . . ?
C15 C22 H22A 109.8 . . ?
N3 C22 H22B 109.8 . . ?
C15 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C25 116.2(16) . . ?
C24 C23 N4 113.6(14) . . ?
C25 C23 N4 109.2(13) . . ?
C24 C23 C26 105.6(13) . . ?
C25 C23 C26 107.6(14) . . ?
N4 C23 C26 103.6(13) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O9 C27 H27A 109.5 . . ?
O9 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O9 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O10 C28 H28A 109.5 . . ?
O10 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O10 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
O3 P1 O4 C13 -38.7(10) . . . . ?
O5 P1 O4 C13 -164.3(9) . . . . ?
C1 P1 O4 C13 88.1(10) . . . . ?
O3 P1 O5 C14 -60.8(12) . . . . ?
O4 P1 O5 C14 62.7(11) . . . . ?
C1 P1 O5 C14 173.4(11) . . . . ?
C8 N1 N2 O2 2.2(19) . . . . ?
C8 N1 N2 C9 -175.8(11) . . . . ?
O3 P1 C1 O1 67.1(10) . . . . ?
O4 P1 C1 O1 -59.4(9) . . . . ?
O5 P1 C1 O1 -165.4(8) . . . . ?
O3 P1 C1 C8 -53.1(10) . . . . ?
O4 P1 C1 C8 -179.6(8) . . . . ?
O5 P1 C1 C8 74.4(9) . . . . ?
O3 P1 C1 C2 179.7(8) . . . . ?
O4 P1 C1 C2 53.2(10) . . . . ?
O5 P1 C1 C2 -52.9(10) . . . . ?
O1 C1 C2 C7 26.5(14) . . . . ?
C8 C1 C2 C7 147.7(11) . . . . ?
P1 C1 C2 C7 -87.8(12) . . . . ?
O1 C1 C2 C3 -154.0(12) . . . . ?
C8 C1 C2 C3 -32.8(16) . . . . ?
P1 C1 C2 C3 91.7(14) . . . . ?
C7 C2 C3 C4 1(2) . . . . ?
C1 C2 C3 C4 -178.1(12) . . . . ?
C7 C2 C3 F1 177.8(11) . . . . ?
C1 C2 C3 F1 -1.8(19) . . . . ?
F1 C3 C4 C5 -177.8(12) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C4 C5 C6 C7 0(2) . . . . ?
C5 C6 C7 C2 0(2) . . . . ?
C3 C2 C7 C6 -0.8(18) . . . . ?
C1 C2 C7 C6 178.8(11) . . . . ?
N2 N1 C8 C1 166.3(11) . . . . ?
O1 C1 C8 N1 69.6(12) . . . . ?
C2 C1 C8 N1 -47.6(13) . . . . ?
P1 C1 C8 N1 -173.0(8) . . . . ?
N1 N2 C9 C11 70.7(15) . . . . ?
O2 N2 C9 C11 -107.6(15) . . . . ?
N1 N2 C9 C12 -50.1(16) . . . . ?
O2 N2 C9 C12 131.7(14) . . . . ?
N1 N2 C9 C10 -170.5(12) . . . . ?
O2 N2 C9 C10 11.3(18) . . . . ?
O8 P2 O9 C27 33.6(14) . . . . ?
O10 P2 O9 C27 -94.5(13) . . . . ?
C15 P2 O9 C27 154.8(13) . . . . ?
O8 P2 O10 C28 -52.9(12) . . . . ?
O9 P2 O10 C28 76.5(12) . . . . ?
C15 P2 O10 C28 -173.6(11) . . . . ?
C22 N3 N4 O7 -3(2) . . . . ?
C22 N3 N4 C23 -179.3(13) . . . . ?
O8 P2 C15 O6 -54.3(11) . . . . ?
O9 P2 C15 O6 -178.3(9) . . . . ?
O10 P2 C15 O6 67.7(10) . . . . ?
O8 P2 C15 C16 70.3(11) . . . . ?
O9 P2 C15 C16 -53.7(11) . . . . ?
O10 P2 C15 C16 -167.8(9) . . . . ?
O8 P2 C15 C22 -164.8(10) . . . . ?
O9 P2 C15 C22 71.2(11) . . . . ?
O10 P2 C15 C22 -42.9(11) . . . . ?
O6 C15 C16 C21 31.4(17) . . . . ?
C22 C15 C16 C21 146.8(13) . . . . ?
P2 C15 C16 C21 -91.0(13) . . . . ?
O6 C15 C16 C17 -148.6(12) . . . . ?
C22 C15 C16 C17 -33.2(17) . . . . ?
P2 C15 C16 C17 89.0(14) . . . . ?
C21 C16 C17 F2 179.3(14) . . . . ?
C15 C16 C17 F2 -1(2) . . . . ?
C21 C16 C17 C18 3(2) . . . . ?
C15 C16 C17 C18 -177.0(13) . . . . ?
F2 C17 C18 C19 -179.1(13) . . . . ?
C16 C17 C18 C19 -3(2) . . . . ?
C17 C18 C19 C20 1(2) . . . . ?
C18 C19 C20 C21 1(2) . . . . ?
C17 C16 C21 C20 -2(2) . . . . ?
C15 C16 C21 C20 178.3(12) . . . . ?
C19 C20 C21 C16 0(2) . . . . ?
N4 N3 C22 C15 174.1(13) . . . . ?
O6 C15 C22 N3 71.3(14) . . . . ?
C16 C15 C22 N3 -50.5(15) . . . . ?
P2 C15 C22 N3 -173.3(10) . . . . ?
N3 N4 C23 C24 173.3(16) . . . . ?
O7 N4 C23 C24 -3(2) . . . . ?
N3 N4 C23 C25 42(2) . . . . ?
O7 N4 C23 C25 -134.6(17) . . . . ?
N3 N4 C23 C26 -72.6(17) . . . . ?
O7 N4 C23 C26 110.9(16) . . . . ?

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
O1 H1 O8 0.83 1.87 2.662(13) 159.6 1_545
O6 H6A O3 0.83 2.05 2.859(14) 165.6 1_565

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.180


