# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_test

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H28 O2 P2'
_chemical_formula_weight         578.54

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   7.874
_cell_length_b                   12.000
_cell_length_c                   14.805
_cell_angle_alpha                90.00
_cell_angle_beta                 94.70
_cell_angle_gamma                90.00
_cell_volume                     1394.2
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4865
_cell_measurement_theta_min      2.1876
_cell_measurement_theta_max      29.1226

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.46
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9084
_exptl_absorpt_correction_T_max  0.9168
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_number            9379
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2732
_reflns_number_gt                2652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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 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^)+(0.0392P)^2^+0.8714P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2732
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.03165(5) 0.79956(3) 0.85323(3) 0.01680(13) Uani 1 1 d . . .
O1 O 0.12123(16) 0.83711(10) 0.77425(8) 0.0234(3) Uani 1 1 d . . .
C8 C 0.1295(2) 0.67996(14) 0.90983(11) 0.0185(3) Uani 1 1 d . . .
C1 C 0.0192(2) 0.90729(13) 0.94119(11) 0.0174(3) Uani 1 1 d . . .
C9 C 0.1853(2) 0.59283(15) 0.85691(12) 0.0222(4) Uani 1 1 d . . .
H9 H 0.1676 0.5969 0.7927 0.027 Uiso 1 1 calc R . .
C4 C 0.4068(2) 1.07503(16) 0.90275(12) 0.0240(4) Uani 1 1 d . . .
H4 H 0.5096 1.0680 0.8738 0.029 Uiso 1 1 calc R . .
C14 C -0.1843(2) 0.76376(14) 0.81244(11) 0.0190(3) Uani 1 1 d . . .
C6 C 0.2325(2) 1.18168(14) 0.99588(11) 0.0208(4) Uani 1 1 d . . .
H6 H 0.2107 1.2493 1.0263 0.025 Uiso 1 1 calc R . .
C13 C 0.1592(2) 0.67387(15) 1.00378(12) 0.0240(4) Uani 1 1 d . . .
H13 H 0.1232 0.7328 1.0406 0.029 Uiso 1 1 calc R . .
C7 C 0.1173(2) 1.08989(13) 1.00236(11) 0.0175(3) Uani 1 1 d . . .
C17 C -0.5097(2) 0.71783(17) 0.73293(12) 0.0290(4) Uani 1 1 d . . .
H17 H -0.6205 0.7023 0.7055 0.035 Uiso 1 1 calc R . .
C3 C 0.2947(2) 0.98873(15) 0.90055(11) 0.0218(4) Uani 1 1 d . . .
H3 H 0.3185 0.9233 0.8678 0.026 Uiso 1 1 calc R . .
C2 C 0.1414(2) 0.99399(13) 0.94641(11) 0.0173(3) Uani 1 1 d . . .
C5 C 0.3715(2) 1.17500(15) 0.94773(12) 0.0245(4) Uani 1 1 d . . .
H5 H 0.4448 1.2375 0.9443 0.029 Uiso 1 1 calc R . .
C19 C -0.2378(2) 0.65407(15) 0.79874(12) 0.0242(4) Uani 1 1 d . . .
H19 H -0.1627 0.5945 0.8161 0.029 Uiso 1 1 calc R . .
C16 C -0.4570(2) 0.82694(17) 0.74611(12) 0.0281(4) Uani 1 1 d . . .
H16 H -0.5319 0.8863 0.7279 0.034 Uiso 1 1 calc R . .
C11 C 0.2929(2) 0.49529(15) 0.99065(13) 0.0256(4) Uani 1 1 d . . .
H11 H 0.3470 0.4318 1.0185 0.031 Uiso 1 1 calc R . .
C18 C -0.4011(2) 0.63142(17) 0.75963(13) 0.0301(4) Uani 1 1 d . . .
H18 H -0.4378 0.5564 0.7513 0.036 Uiso 1 1 calc R . .
C10 C 0.2659(2) 0.50080(15) 0.89702(13) 0.0254(4) Uani 1 1 d . . .
H10 H 0.3025 0.4417 0.8606 0.030 Uiso 1 1 calc R . .
C15 C -0.2959(2) 0.84993(15) 0.78571(12) 0.0242(4) Uani 1 1 d . . .
H15 H -0.2608 0.9251 0.7948 0.029 Uiso 1 1 calc R . .
C12 C 0.2413(3) 0.58181(16) 1.04360(12) 0.0284(4) Uani 1 1 d . . .
H12 H 0.2622 0.5782 1.1076 0.034 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 0.0204(2) 0.0154(2) 0.0146(2) -0.00089(15) 0.00197(16) -0.00049(16)
O1 0.0267(7) 0.0267(7) 0.0174(6) -0.0006(5) 0.0053(5) -0.0042(5)
C8 0.0180(8) 0.0179(8) 0.0196(8) -0.0009(6) 0.0014(6) -0.0009(6)
C1 0.0209(8) 0.0145(7) 0.0167(8) 0.0007(6) 0.0006(6) 0.0014(6)
C9 0.0227(9) 0.0233(9) 0.0204(8) -0.0049(7) 0.0002(7) 0.0000(7)
C4 0.0195(9) 0.0318(10) 0.0212(8) -0.0020(7) 0.0041(7) -0.0022(7)
C14 0.0229(9) 0.0210(8) 0.0131(7) -0.0004(6) 0.0021(6) -0.0005(7)
C6 0.0277(9) 0.0184(8) 0.0164(8) -0.0016(6) 0.0026(7) -0.0033(7)
C13 0.0312(10) 0.0210(8) 0.0202(9) -0.0020(7) 0.0032(7) 0.0041(7)
C7 0.0200(8) 0.0168(8) 0.0153(7) 0.0016(6) -0.0005(6) -0.0008(6)
C17 0.0216(9) 0.0427(11) 0.0225(9) -0.0038(8) 0.0000(7) -0.0012(8)
C3 0.0208(9) 0.0232(9) 0.0214(8) -0.0035(7) 0.0026(7) 0.0008(7)
C2 0.0186(8) 0.0178(8) 0.0152(7) 0.0019(6) -0.0007(6) 0.0007(6)
C5 0.0251(9) 0.0270(9) 0.0213(8) 0.0003(7) 0.0021(7) -0.0091(7)
C19 0.0230(9) 0.0218(9) 0.0274(9) -0.0047(7) 0.0009(7) 0.0013(7)
C16 0.0249(10) 0.0355(10) 0.0239(9) 0.0075(8) 0.0016(7) 0.0053(8)
C11 0.0258(10) 0.0196(9) 0.0310(10) 0.0024(7) -0.0002(7) 0.0025(7)
C18 0.0262(10) 0.0281(10) 0.0361(11) -0.0102(8) 0.0022(8) -0.0041(8)
C10 0.0244(9) 0.0211(9) 0.0304(10) -0.0066(7) 0.0006(7) 0.0018(7)
C15 0.0282(10) 0.0209(9) 0.0235(9) 0.0047(7) 0.0024(7) 0.0005(7)
C12 0.0375(11) 0.0268(10) 0.0205(9) 0.0031(7) 0.0005(8) 0.0061(8)

_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 O1 1.4844(12) . ?
P1 C8 1.8027(17) . ?
P1 C14 1.8093(18) . ?
P1 C1 1.8432(17) . ?
C8 C13 1.393(2) . ?
C8 C9 1.399(2) . ?
C1 C2 1.415(2) . ?
C1 C7 1.415(2) 3_577 ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C4 C3 1.360(3) . ?
C4 C5 1.411(3) . ?
C4 H4 0.9500 . ?
C14 C19 1.392(2) . ?
C14 C15 1.393(2) . ?
C6 C5 1.357(3) . ?
C6 C7 1.435(2) . ?
C6 H6 0.9500 . ?
C13 C12 1.387(3) . ?
C13 H13 0.9500 . ?
C7 C1 1.415(2) 3_577 ?
C7 C2 1.440(2) . ?
C17 C18 1.381(3) . ?
C17 C16 1.382(3) . ?
C17 H17 0.9500 . ?
C3 C2 1.434(2) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C19 C18 1.393(3) . ?
C19 H19 0.9500 . ?
C16 C15 1.382(3) . ?
C16 H16 0.9500 . ?
C11 C12 1.382(3) . ?
C11 C10 1.387(3) . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C10 H10 0.9500 . ?
C15 H15 0.9500 . ?
C12 H12 0.9500 . ?

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
O1 P1 C8 113.28(8) . . ?
O1 P1 C14 107.67(7) . . ?
C8 P1 C14 108.69(8) . . ?
O1 P1 C1 113.57(7) . . ?
C8 P1 C1 105.99(7) . . ?
C14 P1 C1 107.43(8) . . ?
C13 C8 C9 119.03(16) . . ?
C13 C8 P1 122.42(13) . . ?
C9 C8 P1 118.47(13) . . ?
C2 C1 C7 119.75(15) . 3_577 ?
C2 C1 P1 118.63(12) . . ?
C7 C1 P1 121.39(12) 3_577 . ?
C10 C9 C8 120.69(16) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C3 C4 C5 120.40(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C19 C14 C15 119.00(16) . . ?
C19 C14 P1 122.54(13) . . ?
C15 C14 P1 118.16(13) . . ?
C5 C6 C7 122.10(16) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C12 C13 C8 120.02(16) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C1 C7 C6 122.42(15) 3_577 . ?
C1 C7 C2 120.11(15) 3_577 . ?
C6 C7 C2 117.44(15) . . ?
C18 C17 C16 119.94(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C4 C3 C2 121.69(16) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C1 C2 C3 122.46(15) . . ?
C1 C2 C7 119.85(15) . . ?
C3 C2 C7 117.64(15) . . ?
C6 C5 C4 119.81(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C14 C19 C18 120.19(17) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C15 C16 C17 120.23(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C11 C10 120.21(17) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C17 C18 C19 120.09(18) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C9 C10 C11 119.65(16) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C16 C15 C14 120.54(17) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C11 C12 C13 120.38(17) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?

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
O1 P1 C8 C13 134.01(15) . . . . ?
C14 P1 C8 C13 -106.36(16) . . . . ?
C1 P1 C8 C13 8.84(17) . . . . ?
O1 P1 C8 C9 -42.64(16) . . . . ?
C14 P1 C8 C9 76.98(15) . . . . ?
C1 P1 C8 C9 -167.81(13) . . . . ?
O1 P1 C1 C2 -23.70(15) . . . . ?
C8 P1 C1 C2 101.29(13) . . . . ?
C14 P1 C1 C2 -142.65(13) . . . . ?
O1 P1 C1 C7 150.78(13) . . . 3_577 ?
C8 P1 C1 C7 -84.23(14) . . . 3_577 ?
C14 P1 C1 C7 31.83(15) . . . 3_577 ?
C13 C8 C9 C10 1.2(3) . . . . ?
P1 C8 C9 C10 178.00(14) . . . . ?
O1 P1 C14 C19 101.96(15) . . . . ?
C8 P1 C14 C19 -21.10(16) . . . . ?
C1 P1 C14 C19 -135.36(14) . . . . ?
O1 P1 C14 C15 -71.74(15) . . . . ?
C8 P1 C14 C15 165.20(13) . . . . ?
C1 P1 C14 C15 50.93(15) . . . . ?
C9 C8 C13 C12 -0.7(3) . . . . ?
P1 C8 C13 C12 -177.34(15) . . . . ?
C5 C6 C7 C1 174.26(17) . . . 3_577 ?
C5 C6 C7 C2 -7.7(2) . . . . ?
C5 C4 C3 C2 -2.6(3) . . . . ?
C7 C1 C2 C3 171.26(15) 3_577 . . . ?
P1 C1 C2 C3 -14.2(2) . . . . ?
C7 C1 C2 C7 -6.1(3) 3_577 . . . ?
P1 C1 C2 C7 168.44(12) . . . . ?
C4 C3 C2 C1 176.81(16) . . . . ?
C4 C3 C2 C7 -5.7(2) . . . . ?
C1 C7 C2 C1 6.2(3) 3_577 . . . ?
C6 C7 C2 C1 -171.90(15) . . . . ?
C1 C7 C2 C3 -171.36(15) 3_577 . . . ?
C6 C7 C2 C3 10.6(2) . . . . ?
C7 C6 C5 C4 -0.5(3) . . . . ?
C3 C4 C5 C6 5.9(3) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
P1 C14 C19 C18 -174.26(14) . . . . ?
C18 C17 C16 C15 0.2(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C14 C19 C18 C17 1.1(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C12 C11 C10 C9 -0.7(3) . . . . ?
C17 C16 C15 C14 0.3(3) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
P1 C14 C15 C16 173.87(14) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C8 C13 C12 C11 -0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 958068'