# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       zhaodplzu@foxmail.com
_publ_contact_author_name        'Depeng Zhao'
loop_
_publ_author_name
'Depeng Zhao'
'Lijuan Mao'
'Linqing Wang'
'Dongxu Yang'
'Rui Wang'

data_p31
_database_code_depnum_ccdc_archive 'CCDC 842933'
#TrackingRef 'P31.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 O2 P'
_chemical_formula_weight         328.37
_chemical_absolute_configuration none

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           Trigonal
_symmetry_space_group_name_H-M   P3(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   13.410(5)
_cell_length_b                   13.410(5)
_cell_length_c                   8.943(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1392.8(10)
_cell_formula_units_Z            3
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    780
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      17.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6187
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_av_sigmaI/netI    0.1118
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3064
_reflns_number_gt                1806
_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 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^)+(0.0496P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.27(18)
_refine_ls_number_reflns         3064
_refine_ls_number_parameters     211
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.027
_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
C1 C 0.8189(5) 0.9527(6) 0.2789(7) 0.0740(19) Uani 1 1 d . . .
H1 H 0.8559 1.0315 0.2970 0.089 Uiso 1 1 calc R . .
C2 C 0.8728(6) 0.8900(7) 0.3136(9) 0.092(2) Uani 1 1 d . . .
H2 H 0.9471 0.9273 0.3524 0.110 Uiso 1 1 calc R . .
C3 C 0.8166(6) 0.7734(8) 0.2905(8) 0.082(2) Uani 1 1 d . . .
H3 H 0.8526 0.7317 0.3155 0.099 Uiso 1 1 calc R . .
C4 C 0.7096(6) 0.7184(6) 0.2320(7) 0.078(2) Uani 1 1 d . . .
H4 H 0.6722 0.6391 0.2181 0.094 Uiso 1 1 calc R . .
C5 C 0.6550(5) 0.7791(5) 0.1923(6) 0.0600(16) Uani 1 1 d . . .
H5 H 0.5822 0.7411 0.1492 0.072 Uiso 1 1 calc R . .
C6 C 0.7095(4) 0.8967(5) 0.2172(6) 0.0509(14) Uani 1 1 d . . .
C7 C 0.6563(5) 0.9687(5) 0.1808(6) 0.0511(14) Uani 1 1 d . . .
C8 C 0.5316(4) 0.9065(4) 0.1333(6) 0.0471(13) Uani 1 1 d . . .
H8A H 0.4865 0.8546 0.2133 0.056 Uiso 1 1 calc R . .
H8B H 0.5241 0.8595 0.0469 0.056 Uiso 1 1 calc R . .
C9 C 0.4772(4) 0.9820(4) 0.0931(6) 0.0402(12) Uani 1 1 d . . .
C10 C 0.5287(4) 1.0533(4) -0.0503(6) 0.0423(12) Uani 1 1 d . . .
C11 C 0.5912(5) 1.0295(5) -0.1497(7) 0.0628(16) Uani 1 1 d . . .
H11 H 0.6040 0.9686 -0.1305 0.075 Uiso 1 1 calc R . .
C12 C 0.6362(5) 1.0939(6) -0.2785(7) 0.077(2) Uani 1 1 d . . .
H12 H 0.6781 1.0760 -0.3454 0.093 Uiso 1 1 calc R . .
C13 C 0.6184(5) 1.1844(5) -0.3067(7) 0.0667(18) Uani 1 1 d . . .
H13 H 0.6502 1.2294 -0.3915 0.080 Uiso 1 1 calc R . .
C14 C 0.5556(5) 1.2080(5) -0.2126(8) 0.0632(17) Uani 1 1 d . . .
H14 H 0.5409 1.2673 -0.2346 0.076 Uiso 1 1 calc R . .
C15 C 0.5126(4) 1.1454(4) -0.0836(7) 0.0535(15) Uani 1 1 d . . .
H15 H 0.4718 1.1650 -0.0172 0.064 Uiso 1 1 calc R . .
C16 C 0.4833(5) 1.0541(5) 0.2294(6) 0.0626(17) Uani 1 1 d . . .
H16A H 0.5622 1.1094 0.2505 0.094 Uiso 1 1 calc R . .
H16B H 0.4497 1.0046 0.3143 0.094 Uiso 1 1 calc R . .
H16C H 0.4416 1.0936 0.2088 0.094 Uiso 1 1 calc R . .
C17 C 0.3147(5) 0.8004(5) -0.1060(6) 0.0658(17) Uani 1 1 d . . .
H17A H 0.3226 0.8504 -0.1891 0.079 Uiso 1 1 calc R . .
H17B H 0.3801 0.7882 -0.1091 0.079 Uiso 1 1 calc R . .
C18 C 0.2071(7) 0.6865(6) -0.1293(8) 0.098(2) Uani 1 1 d . . .
H18A H 0.1907 0.6406 -0.0406 0.147 Uiso 1 1 calc R . .
H18B H 0.2180 0.6472 -0.2120 0.147 Uiso 1 1 calc R . .
H18C H 0.1439 0.6989 -0.1504 0.147 Uiso 1 1 calc R . .
C19 C 0.2444(5) 0.9506(6) 0.0312(9) 0.088(2) Uani 1 1 d U . .
H19A H 0.2847 1.0237 0.0832 0.106 Uiso 1 1 calc R . .
H19B H 0.2481 0.9673 -0.0748 0.106 Uiso 1 1 calc R . .
C20 C 0.1300(8) 0.8959(9) 0.0745(15) 0.177(4) Uani 1 1 d U . .
H20A H 0.0833 0.8931 -0.0085 0.266 Uiso 1 1 calc R . .
H20B H 0.1208 0.9377 0.1554 0.266 Uiso 1 1 calc R . .
H20C H 0.1066 0.8189 0.1066 0.266 Uiso 1 1 calc R . .
O1 O 0.7132(3) 1.0732(3) 0.1874(5) 0.0840(14) Uani 1 1 d . . .
O2 O 0.2747(3) 0.7947(3) 0.1943(4) 0.0503(10) Uani 1 1 d . . .
P1 P 0.32171(11) 0.87370(11) 0.06375(17) 0.0474(4) Uani 1 1 d U . .

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
C1 0.051(4) 0.066(4) 0.094(6) 0.014(4) -0.008(4) 0.021(3)
C2 0.058(4) 0.101(6) 0.108(6) 0.024(5) -0.021(4) 0.033(4)
C3 0.083(5) 0.110(6) 0.085(5) 0.005(5) -0.011(4) 0.072(5)
C4 0.096(5) 0.076(5) 0.086(5) -0.013(4) -0.032(4) 0.059(4)
C5 0.065(4) 0.068(4) 0.062(4) -0.008(3) -0.018(3) 0.044(4)
C6 0.044(3) 0.057(4) 0.049(4) 0.015(3) 0.003(3) 0.023(3)
C7 0.049(3) 0.044(3) 0.057(4) 0.001(3) -0.001(3) 0.021(3)
C8 0.052(3) 0.041(3) 0.047(3) 0.006(3) 0.001(3) 0.022(3)
C9 0.040(3) 0.038(3) 0.044(3) 0.012(3) 0.007(2) 0.021(2)
C10 0.042(3) 0.041(3) 0.046(3) 0.002(2) 0.002(2) 0.023(2)
C11 0.083(4) 0.057(4) 0.064(4) 0.022(3) 0.030(3) 0.048(3)
C12 0.093(5) 0.080(5) 0.068(5) 0.021(4) 0.032(4) 0.050(4)
C13 0.066(4) 0.059(4) 0.071(5) 0.033(3) 0.022(3) 0.027(3)
C14 0.057(4) 0.048(3) 0.080(5) 0.017(3) 0.001(3) 0.022(3)
C15 0.044(3) 0.043(3) 0.073(4) 0.009(3) 0.005(3) 0.021(3)
C16 0.073(4) 0.065(4) 0.053(4) -0.005(3) 0.013(3) 0.036(3)
C17 0.064(4) 0.071(4) 0.055(4) -0.003(3) -0.009(3) 0.028(3)
C18 0.115(6) 0.075(5) 0.071(5) -0.002(4) -0.010(4) 0.023(5)
C19 0.060(4) 0.079(4) 0.138(7) 0.044(4) 0.021(4) 0.044(4)
C20 0.124(7) 0.184(8) 0.271(11) 0.131(8) 0.084(7) 0.113(7)
O1 0.054(3) 0.048(3) 0.141(4) 0.006(3) -0.010(3) 0.019(2)
O2 0.054(2) 0.043(2) 0.047(2) 0.0149(18) 0.0100(18) 0.0182(18)
P1 0.0440(8) 0.0475(8) 0.0528(9) 0.0080(8) 0.0071(7) 0.0246(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
C1 C6 1.385(7) . ?
C1 C2 1.391(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.348(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(7) . ?
C7 O1 1.217(6) . ?
C7 C8 1.509(7) . ?
C8 C9 1.557(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C16 1.533(7) . ?
C9 C10 1.541(7) . ?
C9 P1 1.870(5) . ?
C10 C11 1.365(7) . ?
C10 C15 1.388(7) . ?
C11 C12 1.384(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.337(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.501(8) . ?
C17 P1 1.785(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.384(9) . ?
C19 P1 1.814(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O2 P1 1.489(3) . ?

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 C1 C2 119.4(6) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 120.1(6) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.6(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.7(5) . . ?
C1 C6 C7 117.0(5) . . ?
C5 C6 C7 123.3(5) . . ?
O1 C7 C6 120.4(5) . . ?
O1 C7 C8 122.2(5) . . ?
C6 C7 C8 117.3(4) . . ?
C7 C8 C9 117.1(4) . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.3 . . ?
C16 C9 C10 113.8(4) . . ?
C16 C9 C8 109.4(4) . . ?
C10 C9 C8 112.6(4) . . ?
C16 C9 P1 106.8(3) . . ?
C10 C9 P1 110.2(3) . . ?
C8 C9 P1 103.4(3) . . ?
C11 C10 C15 117.0(5) . . ?
C11 C10 C9 122.3(4) . . ?
C15 C10 C9 120.7(5) . . ?
C10 C11 C12 121.6(5) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 119.4(6) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.3(6) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 121.4(6) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 P1 116.0(5) . . ?
C18 C17 H17A 108.3 . . ?
P1 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
P1 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 P1 116.8(5) . . ?
C20 C19 H19A 108.1 . . ?
P1 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
P1 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 P1 C17 112.9(2) . . ?
O2 P1 C19 111.8(3) . . ?
C17 P1 C19 106.8(3) . . ?
O2 P1 C9 110.7(2) . . ?
C17 P1 C9 106.2(3) . . ?
C19 P1 C9 108.3(3) . . ?

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
C6 C1 C2 C3 -1.8(11) . . . . ?
C1 C2 C3 C4 1.1(11) . . . . ?
C2 C3 C4 C5 0.8(11) . . . . ?
C3 C4 C5 C6 -2.0(10) . . . . ?
C2 C1 C6 C5 0.6(9) . . . . ?
C2 C1 C6 C7 -179.4(6) . . . . ?
C4 C5 C6 C1 1.2(9) . . . . ?
C4 C5 C6 C7 -178.8(6) . . . . ?
C1 C6 C7 O1 9.3(8) . . . . ?
C5 C6 C7 O1 -170.7(6) . . . . ?
C1 C6 C7 C8 -172.0(5) . . . . ?
C5 C6 C7 C8 8.0(8) . . . . ?
O1 C7 C8 C9 -0.4(8) . . . . ?
C6 C7 C8 C9 -179.1(5) . . . . ?
C7 C8 C9 C16 -60.0(6) . . . . ?
C7 C8 C9 C10 67.6(6) . . . . ?
C7 C8 C9 P1 -173.5(4) . . . . ?
C16 C9 C10 C11 141.4(5) . . . . ?
C8 C9 C10 C11 16.1(7) . . . . ?
P1 C9 C10 C11 -98.7(5) . . . . ?
C16 C9 C10 C15 -38.7(6) . . . . ?
C8 C9 C10 C15 -164.1(5) . . . . ?
P1 C9 C10 C15 81.1(5) . . . . ?
C15 C10 C11 C12 -0.3(8) . . . . ?
C9 C10 C11 C12 179.5(5) . . . . ?
C10 C11 C12 C13 0.5(10) . . . . ?
C11 C12 C13 C14 -1.8(10) . . . . ?
C12 C13 C14 C15 2.9(9) . . . . ?
C11 C10 C15 C14 1.4(8) . . . . ?
C9 C10 C15 C14 -178.5(5) . . . . ?
C13 C14 C15 C10 -2.7(8) . . . . ?
C18 C17 P1 O2 40.0(6) . . . . ?
C18 C17 P1 C19 -83.2(6) . . . . ?
C18 C17 P1 C9 161.4(5) . . . . ?
C20 C19 P1 O2 -28.7(9) . . . . ?
C20 C19 P1 C17 95.1(9) . . . . ?
C20 C19 P1 C9 -150.9(8) . . . . ?
C16 C9 P1 O2 -63.0(4) . . . . ?
C10 C9 P1 O2 172.9(3) . . . . ?
C8 C9 P1 O2 52.4(4) . . . . ?
C16 C9 P1 C17 174.2(4) . . . . ?
C10 C9 P1 C17 50.1(4) . . . . ?
C8 C9 P1 C17 -70.4(4) . . . . ?
C16 C9 P1 C19 59.9(5) . . . . ?
C10 C9 P1 C19 -64.2(4) . . . . ?
C8 C9 P1 C19 175.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.044