# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       ' yujipanxznk@mail.nankai.edu.cn'
_publ_author_name                'Zhiwei Miao'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 783268'
#TrackingRef 'shelxl.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 O6 P'
_chemical_formula_weight         326.27

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                   7.7790(16)
_cell_length_b                   8.9198(18)
_cell_length_c                   12.746(3)
_cell_angle_alpha                99.79(3)
_cell_angle_beta                 105.99(3)
_cell_angle_gamma                107.38(3)
_cell_volume                     780.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2444
_cell_measurement_theta_min      2.611
_cell_measurement_theta_max      27.950

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6143
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2729
_reflns_number_gt                2169
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'crystalclear(Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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^)+(0.0695P)^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     SHELXL
_refine_ls_extinction_coef       0.150(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2729
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_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 0.05299(6) 0.96857(5) 0.19800(4) 0.01875(19) Uani 1 1 d . . .
O1 O -0.00402(16) 0.82752(14) 0.25453(10) 0.0231(3) Uani 1 1 d . . .
O2 O 0.13654(17) 1.12653(14) 0.29972(10) 0.0238(3) Uani 1 1 d . . .
O3 O -0.10334(17) 0.96748(15) 0.10034(10) 0.0246(3) Uani 1 1 d . . .
O4 O 0.31353(17) 1.09361(13) 0.11613(10) 0.0201(3) Uani 1 1 d . . .
H4 H 0.2373 1.0753 0.0502 0.030 Uiso 1 1 calc R . .
O5 O 0.16584(16) 0.65291(13) 0.09370(10) 0.0195(3) Uani 1 1 d . . .
O6 O 0.28893(18) 0.45542(14) 0.08509(11) 0.0307(4) Uani 1 1 d . . .
C1 C 0.2582(2) 0.95415(19) 0.15704(14) 0.0164(4) Uani 1 1 d . . .
C2 C 0.4285(2) 0.9687(2) 0.25845(14) 0.0169(4) Uani 1 1 d . . .
C3 C 0.4155(2) 0.8557(2) 0.32180(15) 0.0196(4) Uani 1 1 d . . .
H3 H 0.3000 0.7636 0.2998 0.023 Uiso 1 1 calc R . .
C4 C 0.5691(3) 0.8763(2) 0.41649(15) 0.0236(4) Uani 1 1 d . . .
H4A H 0.5585 0.7980 0.4587 0.028 Uiso 1 1 calc R . .
C5 C 0.7376(3) 1.0098(2) 0.44990(15) 0.0280(5) Uani 1 1 d . . .
H5 H 0.8428 1.0235 0.5149 0.034 Uiso 1 1 calc R . .
C6 C 0.7520(3) 1.1226(2) 0.38852(16) 0.0310(5) Uani 1 1 d . . .
H6 H 0.8677 1.2147 0.4115 0.037 Uiso 1 1 calc R . .
C7 C 0.5985(2) 1.1034(2) 0.29266(15) 0.0236(4) Uani 1 1 d . . .
H7 H 0.6101 1.1822 0.2508 0.028 Uiso 1 1 calc R . .
C8 C 0.1880(2) 0.79871(19) 0.05596(14) 0.0177(4) Uani 1 1 d . . .
H8 H 0.0615 0.7875 0.0016 0.021 Uiso 1 1 calc R . .
C9 C 0.3252(2) 0.8016(2) -0.00619(14) 0.0188(4) Uani 1 1 d . . .
H9 H 0.3677 0.8822 -0.0429 0.023 Uiso 1 1 calc R . .
C10 C 0.3783(2) 0.6749(2) -0.00222(14) 0.0213(4) Uani 1 1 d . . .
H10 H 0.4656 0.6499 -0.0352 0.026 Uiso 1 1 calc R . .
C11 C 0.2810(2) 0.5790(2) 0.06124(15) 0.0207(4) Uani 1 1 d . . .
C12 C -0.2040(2) 0.7231(2) 0.22591(16) 0.0252(4) Uani 1 1 d . . .
H12A H -0.2617 0.6668 0.1436 0.030 Uiso 1 1 calc R . .
H12B H -0.2787 0.7894 0.2450 0.030 Uiso 1 1 calc R . .
C13 C -0.2066(3) 0.6009(2) 0.29309(19) 0.0395(6) Uani 1 1 d . . .
H13A H -0.1314 0.5368 0.2740 0.059 Uiso 1 1 calc R . .
H13B H -0.3394 0.5278 0.2750 0.059 Uiso 1 1 calc R . .
H13C H -0.1508 0.6579 0.3743 0.059 Uiso 1 1 calc R . .
C14 C 0.1394(3) 1.2822(2) 0.27632(17) 0.0354(5) Uani 1 1 d . . .
H14A H 0.0080 1.2845 0.2542 0.042 Uiso 1 1 calc R . .
H14B H 0.1882 1.2964 0.2133 0.042 Uiso 1 1 calc R . .
C15 C 0.2655(4) 1.4137(2) 0.3799(2) 0.0543(7) Uani 1 1 d . . .
H15A H 0.2209 1.3945 0.4430 0.081 Uiso 1 1 calc R . .
H15B H 0.2627 1.5187 0.3680 0.081 Uiso 1 1 calc R . .
H15C H 0.3971 1.4155 0.3979 0.081 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 0.0199(3) 0.0271(3) 0.0169(3) 0.0132(2) 0.0091(2) 0.0126(2)
O1 0.0149(6) 0.0322(7) 0.0255(7) 0.0184(6) 0.0077(5) 0.0067(5)
O2 0.0338(7) 0.0263(7) 0.0206(7) 0.0120(6) 0.0142(6) 0.0164(6)
O3 0.0248(7) 0.0402(8) 0.0195(7) 0.0169(6) 0.0103(6) 0.0194(6)
O4 0.0248(7) 0.0213(6) 0.0172(7) 0.0122(5) 0.0085(5) 0.0077(5)
O5 0.0207(7) 0.0189(6) 0.0203(7) 0.0086(5) 0.0086(5) 0.0060(5)
O6 0.0399(8) 0.0262(7) 0.0342(8) 0.0150(6) 0.0156(7) 0.0168(6)
C1 0.0183(9) 0.0176(8) 0.0153(9) 0.0092(7) 0.0070(7) 0.0055(7)
C2 0.0171(9) 0.0233(9) 0.0137(9) 0.0054(7) 0.0069(7) 0.0103(7)
C3 0.0190(9) 0.0234(9) 0.0192(9) 0.0083(8) 0.0082(8) 0.0090(7)
C4 0.0258(10) 0.0344(10) 0.0177(10) 0.0120(8) 0.0092(8) 0.0165(8)
C5 0.0200(10) 0.0493(12) 0.0146(9) 0.0064(9) 0.0035(8) 0.0161(9)
C6 0.0199(10) 0.0416(12) 0.0225(11) 0.0062(9) 0.0063(8) 0.0013(8)
C7 0.0232(10) 0.0271(10) 0.0171(10) 0.0067(8) 0.0071(8) 0.0042(8)
C8 0.0173(9) 0.0205(9) 0.0151(9) 0.0077(7) 0.0043(7) 0.0061(7)
C9 0.0204(9) 0.0212(9) 0.0124(9) 0.0052(7) 0.0052(7) 0.0044(7)
C10 0.0197(9) 0.0261(10) 0.0181(10) 0.0054(8) 0.0075(8) 0.0079(8)
C11 0.0188(10) 0.0208(9) 0.0183(9) 0.0028(8) 0.0033(8) 0.0058(8)
C12 0.0180(10) 0.0263(10) 0.0255(10) 0.0056(8) 0.0058(8) 0.0023(8)
C13 0.0338(12) 0.0359(12) 0.0422(13) 0.0207(10) 0.0109(10) 0.0000(9)
C14 0.0587(15) 0.0297(11) 0.0308(12) 0.0171(9) 0.0226(11) 0.0228(10)
C15 0.0659(17) 0.0314(12) 0.0440(15) 0.0140(11) 0.0060(13) -0.0018(12)

_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 1.4776(13) . ?
P1 O1 1.5651(12) . ?
P1 O2 1.5671(14) . ?
P1 C1 1.8430(18) . ?
O1 C12 1.458(2) . ?
O2 C14 1.464(2) . ?
O4 C1 1.4244(18) . ?
O4 H4 0.8400 . ?
O5 C11 1.368(2) . ?
O5 C8 1.4412(19) . ?
O6 C11 1.207(2) . ?
C1 C2 1.529(2) . ?
C1 C8 1.560(2) . ?
C2 C7 1.392(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.492(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.318(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.465(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.495(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.467(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 O1 115.06(8) . . ?
O3 P1 O2 114.13(8) . . ?
O1 P1 O2 103.24(7) . . ?
O3 P1 C1 111.27(8) . . ?
O1 P1 C1 106.43(7) . . ?
O2 P1 C1 105.89(8) . . ?
C12 O1 P1 121.45(11) . . ?
C14 O2 P1 119.11(11) . . ?
C1 O4 H4 109.5 . . ?
C11 O5 C8 109.00(13) . . ?
O4 C1 C2 108.09(13) . . ?
O4 C1 C8 107.90(13) . . ?
C2 C1 C8 114.82(14) . . ?
O4 C1 P1 103.50(11) . . ?
C2 C1 P1 112.39(11) . . ?
C8 C1 P1 109.42(11) . . ?
C7 C2 C3 118.69(16) . . ?
C7 C2 C1 119.27(15) . . ?
C3 C2 C1 121.94(15) . . ?
C4 C3 C2 120.65(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.46(18) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C6 C5 C4 119.49(17) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.77(17) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 119.94(17) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O5 C8 C9 104.52(13) . . ?
O5 C8 C1 111.77(13) . . ?
C9 C8 C1 113.45(14) . . ?
O5 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
C1 C8 H8 109.0 . . ?
C10 C9 C8 109.35(16) . . ?
C10 C9 H9 125.3 . . ?
C8 C9 H9 125.3 . . ?
C9 C10 C11 108.94(16) . . ?
C9 C10 H10 125.5 . . ?
C11 C10 H10 125.5 . . ?
O6 C11 O5 121.05(16) . . ?
O6 C11 C10 130.78(17) . . ?
O5 C11 C10 108.16(14) . . ?
O1 C12 C13 107.48(15) . . ?
O1 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 107.94(17) . . ?
O2 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O2 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O3 P1 O1 C12 -10.94(15) . . . . ?
O2 P1 O1 C12 114.06(14) . . . . ?
C1 P1 O1 C12 -134.68(13) . . . . ?
O3 P1 O2 C14 -31.77(15) . . . . ?
O1 P1 O2 C14 -157.37(13) . . . . ?
C1 P1 O2 C14 90.97(14) . . . . ?
O3 P1 C1 O4 59.07(12) . . . . ?
O1 P1 C1 O4 -174.87(9) . . . . ?
O2 P1 C1 O4 -65.47(11) . . . . ?
O3 P1 C1 C2 175.44(10) . . . . ?
O1 P1 C1 C2 -58.50(13) . . . . ?
O2 P1 C1 C2 50.91(13) . . . . ?
O3 P1 C1 C8 -55.75(13) . . . . ?
O1 P1 C1 C8 70.30(12) . . . . ?
O2 P1 C1 C8 179.71(10) . . . . ?
O4 C1 C2 C7 -0.5(2) . . . . ?
C8 C1 C2 C7 120.01(17) . . . . ?
P1 C1 C2 C7 -114.07(15) . . . . ?
O4 C1 C2 C3 175.91(14) . . . . ?
C8 C1 C2 C3 -63.6(2) . . . . ?
P1 C1 C2 C3 62.31(18) . . . . ?
C7 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C3 C4 -176.87(15) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C1 C2 C7 C6 176.82(15) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C11 O5 C8 C9 1.70(16) . . . . ?
C11 O5 C8 C1 -121.41(14) . . . . ?
O4 C1 C8 O5 168.28(12) . . . . ?
C2 C1 C8 O5 47.69(18) . . . . ?
P1 C1 C8 O5 -79.76(14) . . . . ?
O4 C1 C8 C9 50.40(18) . . . . ?
C2 C1 C8 C9 -70.19(18) . . . . ?
P1 C1 C8 C9 162.36(12) . . . . ?
O5 C8 C9 C10 -1.25(18) . . . . ?
C1 C8 C9 C10 120.76(16) . . . . ?
C8 C9 C10 C11 0.36(19) . . . . ?
C8 O5 C11 O6 178.83(15) . . . . ?
C8 O5 C11 C10 -1.54(17) . . . . ?
C9 C10 C11 O6 -179.68(18) . . . . ?
C9 C10 C11 O5 0.73(19) . . . . ?
P1 O1 C12 C13 179.03(13) . . . . ?
P1 O2 C14 C15 -166.02(15) . . . . ?

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
O4 H4 O3 0.84 1.82 2.6559(19) 170.8 2_575

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.053