# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pro35

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H58 O2 P2'
_chemical_formula_weight         656.82

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'
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                   6.5471(4)
_cell_length_b                   10.5962(6)
_cell_length_c                   14.3323(9)
_cell_angle_alpha                100.773(2)
_cell_angle_beta                 101.934(2)
_cell_angle_gamma                107.345(2)
_cell_volume                     895.07(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5053
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      26.48

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9829
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            11737
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         26.49
_reflns_number_total             3677
_reflns_number_gt                3184
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1000P)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_number_reflns         3677
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.66218(5) 0.19157(3) 0.15927(2) 0.01435(14) Uani 1 1 d . . .
O1 O 0.60879(15) -0.06628(9) 0.14987(7) 0.0141(2) Uani 1 1 d . . .
C1 C 0.1405(2) -0.32777(14) 0.33975(12) 0.0216(3) Uani 1 1 d . . .
H15 H 0.2955 -0.3158 0.3614 0.032 Uiso 1 1 calc R . .
H1 H 0.0843 -0.3702 0.2699 0.032 Uiso 1 1 calc R . .
H16 H 0.0590 -0.3850 0.3741 0.032 Uiso 1 1 calc R . .
C2 C 0.1126(2) -0.18755(14) 0.36196(10) 0.0149(3) Uani 1 1 d . . .
C3 C 0.2477(2) -0.08894(14) 0.31215(10) 0.0136(3) Uani 1 1 d . . .
C4 C 0.3685(2) -0.12877(14) 0.25131(10) 0.0136(3) Uani 1 1 d . . .
H3 H 0.3710 -0.2175 0.2380 0.016 Uiso 1 1 calc R . .
C5 C 0.4859(2) -0.03137(14) 0.21089(9) 0.0130(3) Uani 1 1 d . . .
C6 C 0.7105(2) 0.04378(14) 0.11786(10) 0.0137(3) Uani 1 1 d . . .
C7 C 0.8548(2) 0.01942(14) 0.05644(10) 0.0136(3) Uani 1 1 d . . .
C8 C 0.9326(2) -0.08997(14) 0.05610(10) 0.0156(3) Uani 1 1 d . . .
H4 H 0.8878 -0.1506 0.0934 0.019 Uiso 1 1 calc R . .
C9 C 0.9237(2) 0.10826(14) -0.00033(10) 0.0162(3) Uani 1 1 d . . .
H5 H 0.8725 0.1812 -0.0009 0.019 Uiso 1 1 calc R . .
C10 C 0.1919(2) -0.12598(15) 0.47448(10) 0.0199(3) Uani 1 1 d . . .
H2 H 0.1782 -0.0373 0.4899 0.030 Uiso 1 1 calc R . .
H17 H 0.3450 -0.1171 0.4987 0.030 Uiso 1 1 calc R . .
H18 H 0.1021 -0.1851 0.5052 0.030 Uiso 1 1 calc R . .
C11 C 0.2513(2) 0.04780(14) 0.32988(9) 0.0140(3) Uani 1 1 d . . .
H22 H 0.1672 0.0732 0.3699 0.017 Uiso 1 1 calc R . .
C12 C 0.3716(2) 0.14594(13) 0.29156(9) 0.0124(3) Uani 1 1 d . . .
C13 C 0.4921(2) 0.10353(14) 0.22710(10) 0.0130(3) Uani 1 1 d . . .
C14 C 0.3873(2) 0.29631(13) 0.32135(10) 0.0144(3) Uani 1 1 d . . .
C15 C 0.3138(2) 0.34591(14) 0.23004(10) 0.0182(3) Uani 1 1 d . . .
H8 H 0.3304 0.4408 0.2507 0.027 Uiso 1 1 calc R . .
H7 H 0.1605 0.2926 0.1959 0.027 Uiso 1 1 calc R . .
H6 H 0.4047 0.3353 0.1866 0.027 Uiso 1 1 calc R . .
C16 C 0.2404(2) 0.31793(15) 0.38920(11) 0.0202(3) Uani 1 1 d . . .
H9 H 0.2531 0.4126 0.4052 0.030 Uiso 1 1 calc R . .
H10 H 0.2882 0.2931 0.4489 0.030 Uiso 1 1 calc R . .
H11 H 0.0879 0.2616 0.3559 0.030 Uiso 1 1 calc R . .
C17 C 0.6311(2) 0.38563(14) 0.37802(11) 0.0204(3) Uani 1 1 d . . .
H14 H 0.6433 0.4800 0.3970 0.031 Uiso 1 1 calc R . .
H12 H 0.7257 0.3758 0.3362 0.031 Uiso 1 1 calc R . .
H13 H 0.6760 0.3567 0.4361 0.031 Uiso 1 1 calc R . .
C18 C -0.1358(2) -0.20814(16) 0.32417(11) 0.0214(3) Uani 1 1 d . . .
H20 H -0.1554 -0.1210 0.3383 0.032 Uiso 1 1 calc R . .
H21 H -0.2201 -0.2673 0.3566 0.032 Uiso 1 1 calc R . .
H19 H -0.1871 -0.2490 0.2540 0.032 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_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons

1 0.071 0.500 1.000 145 37


_platon_squeeze_details          
; 
 SQUEEZE (PLATON, A. Spek) was used to treat diffuse solvent 
 contributions.  Total electron count found = 37/unit cell.  Calculated for
 1 hexane (the re'xtal solvent) = 50/unit cell.  The intensive
 properties (density, F(000), etc.) reflect these contributions.  
;

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 C6 1.7117(14) . ?
P1 C13 1.7951(13) . ?
O1 C6 1.3701(16) . ?
O1 C5 1.3769(15) . ?
C1 C2 1.5334(19) . ?
C1 H15 0.9600 . ?
C1 H1 0.9600 . ?
C1 H16 0.9600 . ?
C2 C10 1.5344(19) . ?
C2 C18 1.5381(18) . ?
C2 C3 1.5404(17) . ?
C3 C4 1.3825(17) . ?
C3 C11 1.4157(18) . ?
C4 C5 1.3880(18) . ?
C4 H3 0.9300 . ?
C5 C13 1.3917(19) . ?
C6 C7 1.4625(17) . ?
C7 C9 1.3917(19) . ?
C7 C8 1.3978(19) . ?
C8 C9 1.3868(18) 2_755 ?
C8 H4 0.9300 . ?
C9 C8 1.3868(18) 2_755 ?
C9 H5 0.9300 . ?
C10 H2 0.9600 . ?
C10 H17 0.9600 . ?
C10 H18 0.9600 . ?
C11 C12 1.3812(18) . ?
C11 H22 0.9300 . ?
C12 C13 1.4268(17) . ?
C12 C14 1.5366(18) . ?
C14 C16 1.5358(18) . ?
C14 C15 1.5387(19) . ?
C14 C17 1.5424(19) . ?
C15 H8 0.9600 . ?
C15 H7 0.9600 . ?
C15 H6 0.9600 . ?
C16 H9 0.9600 . ?
C16 H10 0.9600 . ?
C16 H11 0.9600 . ?
C17 H14 0.9600 . ?
C17 H12 0.9600 . ?
C17 H13 0.9600 . ?
C18 H20 0.9600 . ?
C18 H21 0.9600 . ?
C18 H19 0.9600 . ?

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
C6 P1 C13 88.50(6) . . ?
C6 O1 C5 110.30(10) . . ?
C2 C1 H15 109.5 . . ?
C2 C1 H1 109.5 . . ?
H15 C1 H1 109.5 . . ?
C2 C1 H16 109.5 . . ?
H15 C1 H16 109.5 . . ?
H1 C1 H16 109.5 . . ?
C1 C2 C10 108.16(11) . . ?
C1 C2 C18 108.77(11) . . ?
C10 C2 C18 109.25(11) . . ?
C1 C2 C3 111.86(11) . . ?
C10 C2 C3 109.53(10) . . ?
C18 C2 C3 109.23(10) . . ?
C4 C3 C11 118.52(12) . . ?
C4 C3 C2 122.25(12) . . ?
C11 C3 C2 119.22(11) . . ?
C3 C4 C5 117.54(12) . . ?
C3 C4 H3 121.2 . . ?
C5 C4 H3 121.2 . . ?
O1 C5 C4 119.63(12) . . ?
O1 C5 C13 115.32(11) . . ?
C4 C5 C13 125.05(12) . . ?
O1 C6 C7 114.63(11) . . ?
O1 C6 P1 116.22(9) . . ?
C7 C6 P1 129.08(10) . . ?
C9 C7 C8 118.68(12) . . ?
C9 C7 C6 120.27(12) . . ?
C8 C7 C6 121.01(12) . . ?
C9 C8 C7 120.16(12) 2_755 . ?
C9 C8 H4 119.9 2_755 . ?
C7 C8 H4 119.9 . . ?
C8 C9 C7 121.16(13) 2_755 . ?
C8 C9 H5 119.4 2_755 . ?
C7 C9 H5 119.4 . . ?
C2 C10 H2 109.5 . . ?
C2 C10 H17 109.5 . . ?
H2 C10 H17 109.5 . . ?
C2 C10 H18 109.5 . . ?
H2 C10 H18 109.5 . . ?
H17 C10 H18 109.5 . . ?
C12 C11 C3 124.19(12) . . ?
C12 C11 H22 117.9 . . ?
C3 C11 H22 117.9 . . ?
C11 C12 C13 117.05(12) . . ?
C11 C12 C14 121.85(11) . . ?
C13 C12 C14 121.00(11) . . ?
C5 C13 C12 117.60(12) . . ?
C5 C13 P1 109.66(9) . . ?
C12 C13 P1 132.73(10) . . ?
C16 C14 C12 112.09(11) . . ?
C16 C14 C15 107.46(11) . . ?
C12 C14 C15 111.32(11) . . ?
C16 C14 C17 108.01(11) . . ?
C12 C14 C17 108.60(10) . . ?
C15 C14 C17 109.27(11) . . ?
C14 C15 H8 109.5 . . ?
C14 C15 H7 109.5 . . ?
H8 C15 H7 109.5 . . ?
C14 C15 H6 109.5 . . ?
H8 C15 H6 109.5 . . ?
H7 C15 H6 109.5 . . ?
C14 C16 H9 109.5 . . ?
C14 C16 H10 109.5 . . ?
H9 C16 H10 109.5 . . ?
C14 C16 H11 109.5 . . ?
H9 C16 H11 109.5 . . ?
H10 C16 H11 109.5 . . ?
C14 C17 H14 109.5 . . ?
C14 C17 H12 109.5 . . ?
H14 C17 H12 109.5 . . ?
C14 C17 H13 109.5 . . ?
H14 C17 H13 109.5 . . ?
H12 C17 H13 109.5 . . ?
C2 C18 H20 109.5 . . ?
C2 C18 H21 109.5 . . ?
H20 C18 H21 109.5 . . ?
C2 C18 H19 109.5 . . ?
H20 C18 H19 109.5 . . ?
H21 C18 H19 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
C1 C2 C3 C4 2.94(17) . . . . ?
C10 C2 C3 C4 122.85(13) . . . . ?
C18 C2 C3 C4 -117.53(14) . . . . ?
C1 C2 C3 C11 -176.25(12) . . . . ?
C10 C2 C3 C11 -56.35(15) . . . . ?
C18 C2 C3 C11 63.27(15) . . . . ?
C11 C3 C4 C5 -0.24(18) . . . . ?
C2 C3 C4 C5 -179.45(11) . . . . ?
C6 O1 C5 C4 179.80(11) . . . . ?
C6 O1 C5 C13 -0.42(15) . . . . ?
C3 C4 C5 O1 179.98(11) . . . . ?
C3 C4 C5 C13 0.2(2) . . . . ?
C5 O1 C6 C7 177.00(10) . . . . ?
C5 O1 C6 P1 -0.13(13) . . . . ?
C13 P1 C6 O1 0.47(10) . . . . ?
C13 P1 C6 C7 -176.17(13) . . . . ?
O1 C6 C7 C9 164.17(12) . . . . ?
P1 C6 C7 C9 -19.14(19) . . . . ?
O1 C6 C7 C8 -18.11(18) . . . . ?
P1 C6 C7 C8 158.57(11) . . . . ?
C9 C7 C8 C9 0.3(2) . . . 2_755 ?
C6 C7 C8 C9 -177.48(12) . . . 2_755 ?
C8 C7 C9 C8 -0.3(2) . . . 2_755 ?
C6 C7 C9 C8 177.50(12) . . . 2_755 ?
C4 C3 C11 C12 -1.18(19) . . . . ?
C2 C3 C11 C12 178.05(11) . . . . ?
C3 C11 C12 C13 2.50(19) . . . . ?
C3 C11 C12 C14 -173.97(11) . . . . ?
O1 C5 C13 C12 -178.64(11) . . . . ?
C4 C5 C13 C12 1.12(19) . . . . ?
O1 C5 C13 P1 0.75(14) . . . . ?
C4 C5 C13 P1 -179.48(11) . . . . ?
C11 C12 C13 C5 -2.37(18) . . . . ?
C14 C12 C13 C5 174.14(11) . . . . ?
C11 C12 C13 P1 178.40(10) . . . . ?
C14 C12 C13 P1 -5.09(19) . . . . ?
C6 P1 C13 C5 -0.66(10) . . . . ?
C6 P1 C13 C12 178.61(14) . . . . ?
C11 C12 C14 C16 -4.88(17) . . . . ?
C13 C12 C14 C16 178.79(12) . . . . ?
C11 C12 C14 C15 -125.27(13) . . . . ?
C13 C12 C14 C15 58.39(16) . . . . ?
C11 C12 C14 C17 114.38(13) . . . . ?
C13 C12 C14 C17 -61.96(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1007938'
