# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_k1293
_database_code_depnum_ccdc_archive 'CCDC 950629'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H34 N2 O6, C12 H14 N2 2+, 2(F6 P -)'
_chemical_formula_sum            'C34 H48 F12 N4 O6 P2'
_chemical_formula_weight         898.70

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1218(9)
_cell_length_b                   11.2172(12)
_cell_length_c                   11.2671(12)
_cell_angle_alpha                79.387(1)
_cell_angle_beta                 79.478(1)
_cell_angle_gamma                84.213(1)
_cell_volume                     989.55(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3508
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      25.07

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            'Very dark blue'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             466
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   'SAINT v7.12A'

_diffrn_ambient_temperature      223(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 APEX II CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 4K
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            5054
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.07
_reflns_number_total             3465
_reflns_number_gt                2855
_reflns_threshold_expression     >4sigma(I)

_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 4sigma(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)+(0.0661P)²+1.3145P] where P=(Fo²+2Fc²)/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_number_reflns         3465
_refine_ls_number_parameters     264
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.0306(2) 0.20752(16) 0.83500(17) 0.0398(5) Uani 1 1 d . . .
O2 O -0.1637(2) 0.36339(17) 0.98164(19) 0.0437(5) Uani 1 1 d . . .
O3 O -0.1800(3) 0.57652(18) 1.10174(17) 0.0448(5) Uani 1 1 d . . .
H3X H -0.0684 0.6017 1.0824 0.067 Uiso 1 1 d . . .
N1 N 0.3316(3) 0.2861(2) 0.6715(2) 0.0378(5) Uani 1 1 d D . .
H1N H 0.316(4) 0.319(3) 0.7435(17) 0.049 Uiso 1 1 d D . .
N2 N 0.1750(3) 0.7326(2) 0.5952(2) 0.0371(5) Uani 1 1 d . . .
C1 C 0.5267(3) 0.5369(2) 0.4426(2) 0.0271(5) Uani 1 1 d . . .
C2 C 0.4969(3) 0.5024(2) 0.3337(2) 0.0328(5) Uani 1 1 d . . .
H2 H 0.5282 0.5521 0.2576 0.039 Uiso 1 1 calc R . .
C3 C 0.4227(3) 0.3969(2) 0.3396(2) 0.0352(6) Uani 1 1 d . . .
H3 H 0.4062 0.3740 0.2667 0.042 Uiso 1 1 calc R . .
C4 C 0.3708(3) 0.3223(2) 0.4512(2) 0.0326(5) Uani 1 1 d . . .
H4 H 0.3223 0.2494 0.4522 0.039 Uiso 1 1 calc R . .
C5 C 0.3901(3) 0.3547(2) 0.5606(2) 0.0292(5) Uani 1 1 d . . .
C6 C 0.2627(3) 0.1694(2) 0.6822(2) 0.0348(6) Uani 1 1 d . . .
H6A H 0.3533 0.1091 0.6594 0.042 Uiso 1 1 calc R . .
H6B H 0.1824 0.1763 0.6257 0.042 Uiso 1 1 calc R . .
C7 C 0.1765(3) 0.1280(2) 0.8105(2) 0.0369(6) Uani 1 1 d . . .
H7A H 0.1446 0.0444 0.8196 0.044 Uiso 1 1 calc R . .
H7B H 0.2522 0.1298 0.8686 0.044 Uiso 1 1 calc R . .
C8 C -0.0741(4) 0.1632(2) 0.9470(3) 0.0409(6) Uani 1 1 d . . .
H8A H -0.0119 0.1542 1.0153 0.049 Uiso 1 1 calc R . .
H8B H -0.1112 0.0836 0.9438 0.049 Uiso 1 1 calc R . .
C9 C -0.2217(4) 0.2521(3) 0.9648(3) 0.0440(7) Uani 1 1 d . . .
H9A H -0.2779 0.2666 0.8930 0.053 Uiso 1 1 calc R . .
H9B H -0.3022 0.2201 1.0368 0.053 Uiso 1 1 calc R . .
C10 C -0.2947(3) 0.4561(3) 0.9866(3) 0.0423(6) Uani 1 1 d . . .
H10A H -0.3778 0.4349 1.0606 0.051 Uiso 1 1 calc R . .
H10B H -0.3508 0.4629 0.9155 0.051 Uiso 1 1 calc R . .
C11 C -0.2283(4) 0.5755(3) 0.9878(3) 0.0413(6) Uani 1 1 d . . .
H11A H -0.1314 0.5897 0.9223 0.050 Uiso 1 1 calc R . .
H11B H -0.3150 0.6411 0.9727 0.050 Uiso 1 1 calc R . .
C12 C 0.1640(4) 0.7399(3) 0.4767(3) 0.0448(7) Uani 1 1 d . . .
H12 H 0.2033 0.8075 0.4198 0.054 Uiso 1 1 calc R . .
C13 C 0.0966(4) 0.6504(3) 0.4374(3) 0.0412(6) Uani 1 1 d . . .
H13 H 0.0896 0.6573 0.3541 0.049 Uiso 1 1 calc R . .
C14 C 0.0380(3) 0.5490(2) 0.5200(2) 0.0306(5) Uani 1 1 d . . .
C15 C 0.0542(3) 0.5436(3) 0.6414(2) 0.0379(6) Uani 1 1 d . . .
H15 H 0.0176 0.4763 0.7000 0.045 Uiso 1 1 calc R . .
C16 C 0.1230(3) 0.6354(3) 0.6765(3) 0.0406(6) Uani 1 1 d . . .
H16 H 0.1338 0.6301 0.7590 0.049 Uiso 1 1 calc R . .
C17 C 0.2415(4) 0.8332(3) 0.6370(3) 0.0503(8) Uani 1 1 d . . .
H17A H 0.3165 0.8766 0.5696 0.076 Uiso 1 1 calc R . .
H17B H 0.3023 0.8001 0.7037 0.076 Uiso 1 1 calc R . .
H17C H 0.1490 0.8885 0.6652 0.076 Uiso 1 1 calc R . .
P1 P 0.2852(2) 0.06722(18) 0.24757(17) 0.0379(15) Uani 0.60 1 d PG A 1
F1 F 0.3379(4) 0.0312(3) 0.3793(2) 0.0679(10) Uani 0.60 1 d PG A 1
F2 F 0.2324(5) 0.1032(3) 0.1158(2) 0.0940(17) Uani 0.60 1 d PG A 1
F3 F 0.1190(3) -0.0030(3) 0.2965(3) 0.0757(13) Uani 0.60 1 d PG A 1
F4 F 0.4513(3) 0.1374(3) 0.1986(3) 0.0875(16) Uani 0.60 1 d PG A 1
F5 F 0.3824(4) -0.0539(3) 0.2095(3) 0.0925(19) Uani 0.60 1 d PG A 1
F6 F 0.1879(4) 0.1884(2) 0.2856(3) 0.0672(11) Uani 0.60 1 d PG A 1
P1' P 0.2782(4) 0.0692(4) 0.2456(3) 0.049(3) Uiso 0.40 1 d PG B 2
F1' F 0.2550(6) 0.0472(5) 0.3910(3) 0.087(2) Uiso 0.40 1 d PG B 2
F2' F 0.3013(7) 0.0912(6) 0.1002(3) 0.080(2) Uiso 0.40 1 d PG B 2
F3' F 0.1000(5) 0.0181(5) 0.2539(5) 0.078(2) Uiso 0.40 1 d PG B 2
F4' F 0.4563(5) 0.1203(6) 0.2373(5) 0.076(2) Uiso 0.40 1 d PG B 2
F5' F 0.3652(7) -0.0642(4) 0.2452(5) 0.0667(18) Uiso 0.40 1 d PG B 2
F6' F 0.1911(8) 0.2026(4) 0.2461(5) 0.082(3) Uiso 0.40 1 d PG B 2


_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
O1 C7 1.426(3) . ?
O1 C8 1.423(3) . ?
O2 C10 1.412(3) . ?
O2 C9 1.433(3) . ?
O3 C11 1.411(3) . ?
N1 C5 1.372(3) . ?
N1 C6 1.451(3) . ?
N2 C16 1.338(4) . ?
N2 C12 1.341(4) . ?
N2 C17 1.482(4) . ?
C1 C2 1.419(3) . ?
C1 C1 1.422(5) 2_666 ?
C1 C5 1.441(3) 2_666 ?
C2 C3 1.368(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.387(3) . ?
C5 C1 1.441(3) 2_666 ?
C6 C7 1.498(4) . ?
C8 C9 1.489(4) . ?
C10 C11 1.496(4) . ?
C12 C13 1.365(4) . ?
C13 C14 1.394(4) . ?
C14 C15 1.388(4) . ?
C14 C14 1.487(5) 2_566 ?
C15 C16 1.370(4) . ?
P1 F1 1.5898 . ?
P1 F5 1.5899 . ?
P1 F4 1.5900 . ?
P1 F3 1.5900 . ?
P1 F6 1.5901 . ?
P1 F2 1.5902 . ?
P1' F1' 1.5899 . ?
P1' F4' 1.5900 . ?
P1' F6' 1.5900 . ?
P1' F2' 1.5901 . ?
P1' F3' 1.5901 . ?
P1' F5' 1.5901 . ?

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
C7 O1 C8 112.0(2) . . ?
C10 O2 C9 111.5(2) . . ?
C5 N1 C6 122.6(2) . . ?
C16 N2 C12 120.0(2) . . ?
C16 N2 C17 119.7(2) . . ?
C12 N2 C17 120.2(2) . . ?
C2 C1 C1 119.4(3) . 2_666 ?
C2 C1 C5 121.5(2) . 2_666 ?
C1 C1 C5 119.1(3) 2_666 2_666 ?
C3 C2 C1 120.0(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 120.6(2) . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 C1 119.3(2) . 2_666 ?
C4 C5 C1 119.2(2) . 2_666 ?
N1 C6 C7 110.8(2) . . ?
O1 C7 C6 108.3(2) . . ?
O1 C8 C9 108.1(2) . . ?
O2 C9 C8 108.3(2) . . ?
O2 C10 C11 110.8(2) . . ?
O3 C11 C10 110.6(2) . . ?
N2 C12 C13 121.0(3) . . ?
C12 C13 C14 120.6(3) . . ?
C15 C14 C13 116.8(2) . . ?
C15 C14 C14 121.4(3) . 2_566 ?
C13 C14 C14 121.7(3) . 2_566 ?
C16 C15 C14 120.5(3) . . ?
N2 C16 C15 121.1(3) . . ?
F1 P1 F5 90.0 . . ?
F1 P1 F4 90.0 . . ?
F5 P1 F4 90.0 . . ?
F1 P1 F3 90.0 . . ?
F5 P1 F3 90.0 . . ?
F4 P1 F3 180.0 . . ?
F1 P1 F6 90.0 . . ?
F5 P1 F6 180.0 . . ?
F4 P1 F6 90.0 . . ?
F3 P1 F6 90.0 . . ?
F1 P1 F2 180.0 . . ?
F5 P1 F2 90.0 . . ?
F4 P1 F2 90.0 . . ?
F3 P1 F2 90.0 . . ?
F6 P1 F2 90.0 . . ?
F1' P1' F4' 90.0 . . ?
F1' P1' F6' 90.0 . . ?
F4' P1' F6' 90.0 . . ?
F1' P1' F2' 180.0 . . ?
F4' P1' F2' 90.0 . . ?
F6' P1' F2' 90.0 . . ?
F1' P1' F3' 90.0 . . ?
F4' P1' F3' 180.0 . . ?
F6' P1' F3' 90.0 . . ?
F2' P1' F3' 90.0 . . ?
F1' P1' F5' 90.0 . . ?
F4' P1' F5' 90.0 . . ?
F6' P1' F5' 180.0 . . ?
F2' P1' F5' 90.0 . . ?
F3' P1' F5' 90.0 . . ?

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
C1 C1 C2 C3 -2.2(4) 2_666 . . . ?
C5 C1 C2 C3 177.8(2) 2_666 . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C6 N1 C5 C4 6.8(4) . . . . ?
C6 N1 C5 C1 -173.3(2) . . . 2_666 ?
C3 C4 C5 N1 176.4(2) . . . . ?
C3 C4 C5 C1 -3.5(4) . . . 2_666 ?
C5 N1 C6 C7 -168.0(2) . . . . ?
C8 O1 C7 C6 170.1(2) . . . . ?
N1 C6 C7 O1 67.7(3) . . . . ?
C7 O1 C8 C9 179.7(2) . . . . ?
C10 O2 C9 C8 174.0(2) . . . . ?
O1 C8 C9 O2 -65.6(3) . . . . ?
C9 O2 C10 C11 -172.6(2) . . . . ?
O2 C10 C11 O3 -71.9(3) . . . . ?
C16 N2 C12 C13 1.5(4) . . . . ?
C17 N2 C12 C13 -177.2(3) . . . . ?
N2 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C12 C13 C14 C14 179.2(3) . . . 2_566 ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C14 C15 C16 -179.3(3) 2_566 . . . ?
C12 N2 C16 C15 -1.6(4) . . . . ?
C17 N2 C16 C15 177.1(3) . . . . ?
C14 C15 C16 N2 0.4(4) . . . . ?

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
O3 H3X O2 0.9513(19) 1.9435(19) 2.884(3) 169.53(13) 2_567
N1 H1N O3 0.936(10) 2.327(15) 3.215(3) 158(3) 2_567

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.058

