# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_xx
_database_code_depnum_ccdc_archive 'CCDC 1029439'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H62 F2 O4 P2'
_chemical_formula_sum            'C32 H62 F2 O4 P2'
_chemical_formula_weight         610.76

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'
F F 0.0171 0.0103 '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'
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                   8.3768(6)
_cell_length_b                   9.7336(8)
_cell_length_c                   11.0989(9)
_cell_angle_alpha                75.782(4)
_cell_angle_beta                 88.910(4)
_cell_angle_gamma                79.489(4)
_cell_volume                     862.21(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9052
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11427
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         31.50
_reflns_number_total             5585
_reflns_number_gt                3821
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1887P)²+0.1947P] 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_extinction_coef       ?
_refine_ls_number_reflns         5585
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2964
_refine_ls_wR_factor_gt          0.2632
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
P1 P 0.42305(7) 0.72706(6) 0.21784(6) 0.0379(2) Uani 1 1 d . . .
F2 F 0.7488(2) 0.95599(17) -0.15171(17) 0.0570(5) Uani 1 1 d . . .
O3 O 0.4816(2) 0.5884(2) 0.18438(19) 0.0485(5) Uani 1 1 d . . .
C4 C 0.4655(3) 0.8793(3) 0.0943(2) 0.0383(5) Uani 1 1 d . . .
C5 C 0.5935(3) 0.8621(2) 0.0137(2) 0.0385(5) Uani 1 1 d . . .
C6 C 0.6217(3) 0.9804(3) -0.0775(2) 0.0412(5) Uani 1 1 d . . .
C7 C 0.5214(4) 0.7403(3) 0.3567(3) 0.0505(6) Uani 1 1 d . . .
H7 H 0.4927 0.6647 0.4251 0.061 Uiso 1 1 calc R . .
C8 C 0.2048(3) 0.7495(3) 0.2421(3) 0.0469(6) Uani 1 1 d . . .
H8 H 0.1699 0.8344 0.2752 0.056 Uiso 1 1 calc R . .
C9 C 0.7321(3) 0.3029(3) 0.3731(3) 0.0498(6) Uani 1 1 d . . .
H9A H 0.7361 0.2403 0.4562 0.060 Uiso 1 1 calc R . .
H9B H 0.7472 0.3971 0.3802 0.060 Uiso 1 1 calc R . .
C10 C 0.5765(3) 0.3153(3) 0.3147(3) 0.0551(7) Uani 1 1 d . . .
H10A H 0.5489 0.4080 0.2571 0.083 Uiso 1 1 calc R . .
H10B H 0.4955 0.3052 0.3770 0.083 Uiso 1 1 calc R . .
H10C H 0.5813 0.2410 0.2710 0.083 Uiso 1 1 calc R . .
C11 C 0.4690(5) 0.8817(4) 0.3930(3) 0.0678(9) Uani 1 1 d . . .
H11A H 0.4955 0.9591 0.3283 0.102 Uiso 1 1 calc R . .
H11B H 0.5243 0.8781 0.4690 0.102 Uiso 1 1 calc R . .
H11C H 0.3539 0.8976 0.4047 0.102 Uiso 1 1 calc R . .
C3 C 0.6603(5) 0.6555(3) -0.0627(3) 0.0610(8) Uani 1 1 d . . .
H3A H 0.6598 0.7144 -0.1459 0.092 Uiso 1 1 calc R . .
H3B H 0.5555 0.6295 -0.0458 0.092 Uiso 1 1 calc R . .
H3C H 0.7412 0.5697 -0.0541 0.092 Uiso 1 1 calc R . .
C12 C 0.8608(4) 0.2448(4) 0.3009(3) 0.0629(8) Uani 1 1 d . . .
C13 C 0.1760(4) 0.6136(4) 0.3396(4) 0.0674(9) Uani 1 1 d . . .
H13A H 0.2178 0.5295 0.3103 0.101 Uiso 1 1 calc R . .
H13B H 0.0616 0.6191 0.3528 0.101 Uiso 1 1 calc R . .
H13C H 0.2306 0.6078 0.4165 0.101 Uiso 1 1 calc R . .
C14 C 0.1117(4) 0.7682(5) 0.1230(4) 0.0730(10) Uani 1 1 d . . .
H14A H 0.1119 0.8630 0.0710 0.109 Uiso 1 1 calc R . .
H14B H 0.0018 0.7564 0.1413 0.109 Uiso 1 1 calc R . .
H14C H 0.1619 0.6973 0.0805 0.109 Uiso 1 1 calc R . .
C15 C 0.8684(6) 0.3490(5) 0.1786(4) 0.0804(11) Uani 1 1 d . . .
H15A H 0.7690 0.3625 0.1321 0.121 Uiso 1 1 calc R . .
H15B H 0.9578 0.3121 0.1331 0.121 Uiso 1 1 calc R . .
H15C H 0.8833 0.4397 0.1920 0.121 Uiso 1 1 calc R . .
C16 C 0.7054(4) 0.7064(5) 0.3456(4) 0.0712(9) Uani 1 1 d . . .
H16A H 0.7388 0.6063 0.3469 0.107 Uiso 1 1 calc R . .
H16B H 0.7568 0.7271 0.4140 0.107 Uiso 1 1 calc R . .
H16C H 0.7363 0.7646 0.2688 0.107 Uiso 1 1 calc R . .
C17 C 0.8350(7) 0.0977(5) 0.2833(6) 0.1001(15) Uani 1 1 d . . .
H17A H 0.8189 0.0358 0.3627 0.150 Uiso 1 1 calc R . .
H17B H 0.9289 0.0540 0.2461 0.150 Uiso 1 1 calc R . .
H17C H 0.7413 0.1117 0.2302 0.150 Uiso 1 1 calc R . .
C18 C 1.0058(6) 0.2259(6) 0.3850(5) 0.1005(15) Uani 1 1 d . . .
H18A H 1.0132 0.3167 0.4019 0.151 Uiso 1 1 calc R . .
H18B H 1.1026 0.1919 0.3452 0.151 Uiso 1 1 calc R . .
H18C H 0.9944 0.1570 0.4616 0.151 Uiso 1 1 calc R . .
O1 O 0.6966(2) 0.73400(19) 0.02322(18) 0.0453(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
P1 0.0374(3) 0.0366(3) 0.0381(3) -0.0063(2) 0.0048(2) -0.0072(2)
F2 0.0553(10) 0.0451(9) 0.0626(10) -0.0074(7) 0.0308(8) 0.0006(7)
O3 0.0525(11) 0.0379(9) 0.0526(11) -0.0092(8) 0.0076(8) -0.0053(8)
C4 0.0376(11) 0.0371(11) 0.0383(11) -0.0074(9) 0.0066(8) -0.0048(9)
C5 0.0356(11) 0.0366(11) 0.0408(11) -0.0088(9) 0.0039(8) -0.0013(8)
C6 0.0372(11) 0.0397(11) 0.0431(12) -0.0090(9) 0.0122(9) -0.0011(9)
C7 0.0578(16) 0.0543(15) 0.0398(13) -0.0068(11) -0.0002(11) -0.0178(12)
C8 0.0374(12) 0.0509(14) 0.0528(14) -0.0127(11) 0.0090(10) -0.0100(10)
C9 0.0499(14) 0.0536(15) 0.0397(13) -0.0054(11) 0.0014(10) -0.0022(11)
C10 0.0434(13) 0.0446(14) 0.0659(18) 0.0061(12) -0.0002(12) -0.0059(11)
C11 0.084(2) 0.072(2) 0.0571(19) -0.0287(16) 0.0064(16) -0.0215(18)
C3 0.082(2) 0.0450(14) 0.0557(17) -0.0193(13) 0.0146(15) -0.0038(14)
C12 0.0588(18) 0.0571(17) 0.066(2) -0.0084(15) 0.0019(15) -0.0026(14)
C13 0.0550(18) 0.070(2) 0.077(2) -0.0084(17) 0.0206(15) -0.0259(16)
C14 0.0506(17) 0.098(3) 0.068(2) -0.0132(19) -0.0087(15) -0.0183(18)
C15 0.089(3) 0.084(3) 0.063(2) -0.0091(19) 0.0119(19) -0.018(2)
C16 0.0540(17) 0.088(3) 0.073(2) -0.0233(19) -0.0132(15) -0.0101(17)
C17 0.092(3) 0.063(2) 0.142(5) -0.023(3) -0.004(3) -0.008(2)
C18 0.080(3) 0.102(3) 0.108(4) -0.013(3) -0.028(3) -0.002(3)
O1 0.0423(9) 0.0365(8) 0.0520(10) -0.0085(7) 0.0071(7) 0.0020(7)

_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 1.4824(19) . ?
P1 C7 1.805(3) . ?
P1 C8 1.824(3) . ?
P1 C4 1.838(2) . ?
F2 C6 1.356(3) . ?
C4 C6 1.396(3) 2_675 ?
C4 C5 1.396(3) . ?
C5 O1 1.363(3) . ?
C5 C6 1.388(4) . ?
C6 C4 1.396(3) 2_675 ?
C7 C11 1.514(4) . ?
C7 C16 1.525(5) . ?
C8 C14 1.503(5) . ?
C8 C13 1.544(4) . ?
C9 C10 1.439(4) . ?
C9 C12 1.447(4) . ?
C3 O1 1.428(4) . ?
C12 C15 1.489(5) . ?
C12 C18 1.503(6) . ?
C12 C17 1.545(6) . ?

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 C7 113.07(13) . . ?
O3 P1 C8 109.77(13) . . ?
C7 P1 C8 108.28(14) . . ?
O3 P1 C4 110.81(11) . . ?
C7 P1 C4 105.58(12) . . ?
C8 P1 C4 109.19(12) . . ?
C6 C4 C5 115.5(2) 2_675 . ?
C6 C4 P1 123.06(18) 2_675 . ?
C5 C4 P1 121.36(18) . . ?
O1 C5 C6 118.0(2) . . ?
O1 C5 C4 122.7(2) . . ?
C6 C5 C4 119.3(2) . . ?
F2 C6 C5 116.1(2) . . ?
F2 C6 C4 118.7(2) . 2_675 ?
C5 C6 C4 125.1(2) . 2_675 ?
C11 C7 C16 111.0(3) . . ?
C11 C7 P1 115.1(2) . . ?
C16 C7 P1 109.9(2) . . ?
C14 C8 C13 111.1(3) . . ?
C14 C8 P1 111.4(2) . . ?
C13 C8 P1 106.7(2) . . ?
C10 C9 C12 110.3(3) . . ?
C9 C12 C15 109.9(3) . . ?
C9 C12 C18 100.9(3) . . ?
C15 C12 C18 113.4(4) . . ?
C9 C12 C17 110.5(3) . . ?
C15 C12 C17 111.0(4) . . ?
C18 C12 C17 110.7(4) . . ?
C5 O1 C3 114.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        31.50
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.100
