# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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
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data_KASC192
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
Methyl (2S)-hydroxy-2-(2-oxo-(4R),(6R)-diphenyl-1,3,2-dioxaphosphorinan-2-yl) acetate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 O6 P'
_chemical_formula_sum            'C18 H19 O6 P'
_chemical_formula_weight         362.30

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           orthorhombic
_symmetry_space_group_name_H-M   P212121
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   9.7943(4)
_cell_length_b                   10.0856(4)
_cell_length_c                   17.1604(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1695.13(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9469
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9351
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 X8 APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            291851
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0119
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         30.20
_reflns_number_total             5009
_reflns_number_gt                4764
_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^)+(0.0473P)^2^+0.4725P] 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   -0.03(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5009
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0837
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.26669(3) 0.07836(3) 0.973775(18) 0.02067(7) Uani 1 1 d . . .
O1 O 0.07295(13) 0.17657(10) 1.06306(7) 0.0367(3) Uani 1 1 d . . .
H1 H 0.0192 0.2412 1.0591 0.055 Uiso 1 1 calc R . .
O2 O 0.11080(16) 0.33949(11) 0.93130(6) 0.0435(3) Uani 1 1 d . . .
O3 O 0.27228(14) 0.43366(12) 1.00505(12) 0.0640(5) Uani 1 1 d . . .
O4 O 0.40044(11) 0.11257(10) 0.94106(7) 0.0310(2) Uani 1 1 d . . .
O5 O 0.27075(10) -0.04650(9) 1.02836(6) 0.02708(19) Uani 1 1 d . . .
O6 O 0.15812(11) 0.05083(9) 0.90969(5) 0.02515(19) Uani 1 1 d . . .
C1 C 0.17597(12) -0.15828(12) 1.02575(7) 0.0204(2) Uani 1 1 d . . .
H1A H 0.2168 -0.2303 0.9932 0.024 Uiso 1 1 calc R . .
C2 C 0.04143(12) -0.11591(13) 0.98956(7) 0.0207(2) Uani 1 1 d . . .
H2A H -0.0030 -0.0504 1.0242 0.025 Uiso 1 1 calc R . .
H2B H -0.0194 -0.1941 0.9860 0.025 Uiso 1 1 calc R . .
C3 C 0.05706(13) -0.05537(12) 0.90889(7) 0.0208(2) Uani 1 1 d . . .
H3 H -0.0327 -0.0150 0.8945 0.025 Uiso 1 1 calc R . .
C4 C 0.09503(13) -0.15158(12) 0.84512(7) 0.0192(2) Uani 1 1 d . . .
C5 C 0.22987(15) -0.17887(14) 0.82589(8) 0.0289(3) Uani 1 1 d . . .
H5 H 0.3020 -0.1360 0.8530 0.035 Uiso 1 1 calc R . .
C6 C 0.25917(15) -0.26931(15) 0.76682(9) 0.0332(3) Uani 1 1 d . . .
H6 H 0.3514 -0.2883 0.7539 0.040 Uiso 1 1 calc R . .
C7 C 0.15500(15) -0.33141(14) 0.72704(8) 0.0281(3) Uani 1 1 d . . .
H7 H 0.1756 -0.3926 0.6866 0.034 Uiso 1 1 calc R . .
C8 C 0.02081(15) -0.30478(15) 0.74590(9) 0.0304(3) Uani 1 1 d . . .
H8 H -0.0510 -0.3481 0.7188 0.037 Uiso 1 1 calc R . .
C9 C -0.00896(13) -0.21446(14) 0.80454(8) 0.0257(3) Uani 1 1 d . . .
H9 H -0.1014 -0.1955 0.8170 0.031 Uiso 1 1 calc R . .
C10 C 0.15676(12) -0.20925(12) 1.10743(7) 0.0205(2) Uani 1 1 d . . .
C11 C 0.16815(15) -0.12734(15) 1.17193(8) 0.0272(3) Uani 1 1 d . . .
H11 H 0.1899 -0.0362 1.1654 0.033 Uiso 1 1 calc R . .
C12 C 0.14774(16) -0.17887(19) 1.24614(8) 0.0353(3) Uani 1 1 d . . .
H12 H 0.1570 -0.1230 1.2904 0.042 Uiso 1 1 calc R . .
C13 C 0.11405(16) -0.3110(2) 1.25594(9) 0.0392(4) Uani 1 1 d . . .
H13 H 0.1006 -0.3458 1.3068 0.047 Uiso 1 1 calc R . .
C14 C 0.10000(16) -0.39233(16) 1.19176(10) 0.0365(3) Uani 1 1 d . . .
H14 H 0.0755 -0.4828 1.1984 0.044 Uiso 1 1 calc R . .
C15 C 0.12179(14) -0.34171(14) 1.11728(8) 0.0275(3) Uani 1 1 d . . .
H15 H 0.1127 -0.3979 1.0731 0.033 Uiso 1 1 calc R . .
C16 C 0.20165(15) 0.21266(13) 1.03416(8) 0.0279(3) Uani 1 1 d . . .
H16 H 0.2647 0.2235 1.0795 0.033 Uiso 1 1 calc R . .
C17 C 0.20162(15) 0.34211(13) 0.98842(9) 0.0330(3) Uani 1 1 d . . .
C18 C 0.0951(3) 0.46064(17) 0.88650(12) 0.0539(5) Uani 1 1 d . . .
H18A H 0.0256 0.4474 0.8461 0.081 Uiso 1 1 calc R . .
H18B H 0.1823 0.4835 0.8619 0.081 Uiso 1 1 calc R . .
H18C H 0.0667 0.5328 0.9212 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 0.02208(14) 0.01937(13) 0.02055(13) 0.00083(10) 0.00083(11) 0.00027(11)
O1 0.0414(6) 0.0265(5) 0.0423(6) 0.0027(4) 0.0202(5) 0.0051(4)
O2 0.0819(10) 0.0213(5) 0.0273(5) 0.0033(4) 0.0021(6) -0.0069(5)
O3 0.0366(6) 0.0254(5) 0.1302(14) -0.0026(7) -0.0070(8) -0.0073(5)
O4 0.0272(5) 0.0274(5) 0.0382(5) 0.0035(4) 0.0081(4) -0.0010(4)
O5 0.0225(4) 0.0281(4) 0.0307(4) 0.0103(4) -0.0058(4) -0.0038(3)
O6 0.0367(5) 0.0191(4) 0.0197(4) 0.0009(3) -0.0041(4) -0.0032(4)
C1 0.0199(5) 0.0209(5) 0.0203(5) 0.0015(4) -0.0002(4) 0.0004(4)
C2 0.0184(5) 0.0244(5) 0.0194(5) 0.0010(4) -0.0012(4) 0.0016(4)
C3 0.0212(5) 0.0214(5) 0.0198(5) -0.0004(4) -0.0032(4) 0.0027(4)
C4 0.0205(5) 0.0196(5) 0.0176(5) 0.0005(4) -0.0014(4) -0.0009(4)
C5 0.0206(6) 0.0306(6) 0.0355(7) -0.0111(5) -0.0002(5) -0.0039(5)
C6 0.0229(6) 0.0346(7) 0.0419(7) -0.0140(6) 0.0082(6) -0.0036(5)
C7 0.0330(7) 0.0264(6) 0.0247(6) -0.0060(5) 0.0023(5) -0.0020(5)
C8 0.0289(7) 0.0328(7) 0.0296(7) -0.0086(5) -0.0071(5) -0.0041(5)
C9 0.0191(5) 0.0298(6) 0.0283(6) -0.0035(5) -0.0029(5) -0.0008(5)
C10 0.0174(5) 0.0238(5) 0.0204(5) 0.0029(4) -0.0007(4) 0.0025(4)
C11 0.0261(6) 0.0313(6) 0.0243(6) -0.0019(5) -0.0019(5) 0.0039(5)
C12 0.0294(7) 0.0555(10) 0.0209(6) 0.0000(6) 0.0006(5) 0.0118(7)
C13 0.0261(7) 0.0629(11) 0.0287(7) 0.0200(7) 0.0057(6) 0.0129(7)
C14 0.0280(7) 0.0356(8) 0.0459(8) 0.0212(7) 0.0047(6) 0.0047(6)
C15 0.0269(6) 0.0244(6) 0.0312(7) 0.0049(5) -0.0004(5) 0.0019(5)
C16 0.0329(7) 0.0281(6) 0.0227(6) -0.0068(5) 0.0025(5) -0.0024(5)
C17 0.0344(7) 0.0203(6) 0.0441(8) -0.0067(5) 0.0169(6) -0.0010(5)
C18 0.0892(16) 0.0268(7) 0.0458(10) 0.0128(7) 0.0178(10) 0.0062(9)

_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 O4 1.4664(10) . ?
P1 O6 1.5547(10) . ?
P1 O5 1.5700(9) . ?
P1 C16 1.8204(14) . ?
O1 C16 1.4027(18) . ?
O1 H1 0.8400 . ?
O2 C17 1.324(2) . ?
O2 C18 1.4517(19) . ?
O3 C17 1.1886(19) . ?
O5 C1 1.4610(14) . ?
O6 C3 1.4584(15) . ?
C1 C10 1.5048(17) . ?
C1 C2 1.5182(16) . ?
C1 H1A 1.0000 . ?
C2 C3 1.5208(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5091(16) . ?
C3 H3 1.0000 . ?
C4 C9 1.3872(17) . ?
C4 C5 1.3888(18) . ?
C5 C6 1.3936(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3856(18) . ?
C10 C15 1.3895(18) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.523(2) . ?
C16 H16 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O4 P1 O6 112.48(6) . . ?
O4 P1 O5 113.24(6) . . ?
O6 P1 O5 107.22(5) . . ?
O4 P1 C16 110.82(6) . . ?
O6 P1 C16 107.22(6) . . ?
O5 P1 C16 105.43(6) . . ?
C16 O1 H1 109.5 . . ?
C17 O2 C18 116.52(15) . . ?
C1 O5 P1 125.77(8) . . ?
C3 O6 P1 127.02(8) . . ?
O5 C1 C10 108.33(10) . . ?
O5 C1 C2 110.29(10) . . ?
C10 C1 C2 111.64(10) . . ?
O5 C1 H1A 108.8 . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C1 C2 C3 113.46(10) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O6 C3 C4 108.17(10) . . ?
O6 C3 C2 110.77(9) . . ?
C4 C3 C2 115.26(10) . . ?
O6 C3 H3 107.4 . . ?
C4 C3 H3 107.4 . . ?
C2 C3 H3 107.4 . . ?
C9 C4 C5 119.23(11) . . ?
C9 C4 C3 118.49(11) . . ?
C5 C4 C3 122.28(11) . . ?
C4 C5 C6 119.89(12) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.35(13) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.04(13) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 119.85(12) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 120.64(12) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C15 119.73(13) . . ?
C11 C10 C1 122.03(11) . . ?
C15 C10 C1 118.20(12) . . ?
C10 C11 C12 119.82(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.40(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.96(13) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.95(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.12(14) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
O1 C16 C17 113.85(12) . . ?
O1 C16 P1 108.83(9) . . ?
C17 C16 P1 110.15(9) . . ?
O1 C16 H16 107.9 . . ?
C17 C16 H16 107.9 . . ?
P1 C16 H16 107.9 . . ?
O3 C17 O2 125.77(16) . . ?
O3 C17 C16 122.81(17) . . ?
O2 C17 C16 111.38(12) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O4 P1 O5 C1 -132.82(10) . . . . ?
O6 P1 O5 C1 -8.16(12) . . . . ?
C16 P1 O5 C1 105.86(11) . . . . ?
O4 P1 O6 C3 137.65(10) . . . . ?
O5 P1 O6 C3 12.53(12) . . . . ?
C16 P1 O6 C3 -100.28(11) . . . . ?
P1 O5 C1 C10 -146.57(9) . . . . ?
P1 O5 C1 C2 -24.12(14) . . . . ?
O5 C1 C2 C3 55.77(13) . . . . ?
C10 C1 C2 C3 176.26(10) . . . . ?
P1 O6 C3 C4 -110.96(11) . . . . ?
P1 O6 C3 C2 16.25(14) . . . . ?
C1 C2 C3 O6 -52.06(13) . . . . ?
C1 C2 C3 C4 71.15(14) . . . . ?
O6 C3 C4 C9 -145.72(11) . . . . ?
C2 C3 C4 C9 89.70(14) . . . . ?
O6 C3 C4 C5 34.23(16) . . . . ?
C2 C3 C4 C5 -90.34(15) . . . . ?
C9 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 C6 179.56(13) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C5 C4 C9 C8 0.7(2) . . . . ?
C3 C4 C9 C8 -179.36(13) . . . . ?
C7 C8 C9 C4 -0.7(2) . . . . ?
O5 C1 C10 C11 29.21(15) . . . . ?
C2 C1 C10 C11 -92.43(14) . . . . ?
O5 C1 C10 C15 -153.12(11) . . . . ?
C2 C1 C10 C15 85.25(14) . . . . ?
C15 C10 C11 C12 1.5(2) . . . . ?
C1 C10 C11 C12 179.17(13) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C11 C10 C15 C14 -0.8(2) . . . . ?
C1 C10 C15 C14 -178.55(12) . . . . ?
C13 C14 C15 C10 -0.4(2) . . . . ?
O4 P1 C16 O1 179.03(9) . . . . ?
O6 P1 C16 O1 55.93(11) . . . . ?
O5 P1 C16 O1 -58.10(11) . . . . ?
O4 P1 C16 C17 53.57(12) . . . . ?
O6 P1 C16 C17 -69.53(11) . . . . ?
O5 P1 C16 C17 176.44(10) . . . . ?
C18 O2 C17 O3 -1.4(2) . . . . ?
C18 O2 C17 C16 176.23(13) . . . . ?
O1 C16 C17 O3 123.19(17) . . . . ?
P1 C16 C17 O3 -114.26(16) . . . . ?
O1 C16 C17 O2 -54.50(16) . . . . ?
P1 C16 C17 O2 68.05(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.20
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 952037'
#######################################################################
#
#                 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_KASC192B
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
Methyl (2R)-hydroxy-2-(2-oxo-(4R),(6R)-diphenyl-1,3,2-dioxaphosphorinan-2-yl) acetate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H19 O6 P), C H2 Cl2'
_chemical_formula_sum            'C37 H40 Cl2 O12 P2'
_chemical_formula_weight         809.53

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   10.9242(3)
_cell_length_b                   9.4730(3)
_cell_length_c                   18.5505(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.287(2)
_cell_angle_gamma                90.00
_cell_volume                     1914.33(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      29.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8334
_exptl_absorpt_correction_T_max  0.9254
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 X8 APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36832
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         30.11
_reflns_number_total             11113
_reflns_number_gt                10031
_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^)+(0.0495P)^2^+0.2669P] 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   0.00(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11113
_refine_ls_number_parameters     480
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.87789(4) 0.82053(4) 0.97750(2) 0.01803(8) Uani 1 1 d . . .
O1 O 0.73794(10) 0.80771(13) 0.95339(6) 0.0229(2) Uani 1 1 d . . .
O2 O 0.90403(11) 0.72076(13) 1.04382(6) 0.0233(2) Uani 1 1 d . . .
O3 O 0.91883(11) 0.96534(13) 0.99301(6) 0.0248(2) Uani 1 1 d . . .
O4 O 0.94140(12) 0.59532(13) 0.90155(7) 0.0276(3) Uani 1 1 d . . .
H40 H 0.9828 0.5577 0.9364 0.041 Uiso 1 1 calc R . .
O5 O 0.84054(13) 0.74515(15) 0.78875(7) 0.0344(3) Uani 1 1 d . . .
O6 O 0.95932(12) 0.92964(14) 0.82257(7) 0.0291(3) Uani 1 1 d . . .
C1 C 0.71992(16) 0.57944(18) 1.01013(9) 0.0241(3) Uani 1 1 d . . .
H1A H 0.7478 0.5358 0.9657 0.029 Uiso 1 1 calc R . .
H1B H 0.6616 0.5136 1.0309 0.029 Uiso 1 1 calc R . .
C2 C 0.65481(14) 0.71684(18) 0.99074(9) 0.0221(3) Uani 1 1 d . . .
H2 H 0.6320 0.7647 1.0359 0.026 Uiso 1 1 calc R . .
C3 C 0.54150(16) 0.6940(2) 0.94123(10) 0.0267(3) Uani 1 1 d . . .
C4 C 0.43021(18) 0.6807(3) 0.97092(12) 0.0409(5) Uani 1 1 d . . .
H4 H 0.4248 0.6967 1.0211 0.049 Uiso 1 1 calc R . .
C5 C 0.32596(19) 0.6439(3) 0.92754(14) 0.0498(6) Uani 1 1 d . . .
H5 H 0.2500 0.6314 0.9486 0.060 Uiso 1 1 calc R . .
C6 C 0.3319(2) 0.6256(3) 0.85502(15) 0.0508(6) Uani 1 1 d . . .
H6 H 0.2601 0.6025 0.8253 0.061 Uiso 1 1 calc R . .
C7 C 0.4429(2) 0.6408(4) 0.82499(14) 0.0651(8) Uani 1 1 d . . .
H7 H 0.4479 0.6265 0.7746 0.078 Uiso 1 1 calc R . .
C8 C 0.5468(2) 0.6767(4) 0.86796(12) 0.0545(7) Uani 1 1 d . . .
H8 H 0.6226 0.6896 0.8468 0.065 Uiso 1 1 calc R . .
C9 C 0.83035(15) 0.60140(17) 1.06447(9) 0.0220(3) Uani 1 1 d . . .
H9 H 0.8826 0.5147 1.0645 0.026 Uiso 1 1 calc R . .
C10 C 0.79342(15) 0.62479(19) 1.14059(9) 0.0236(3) Uani 1 1 d . . .
C11 C 0.7987(2) 0.7539(2) 1.17394(10) 0.0368(4) Uani 1 1 d . . .
H11 H 0.8285 0.8338 1.1497 0.044 Uiso 1 1 calc R . .
C12 C 0.7603(2) 0.7674(3) 1.24350(12) 0.0489(6) Uani 1 1 d . . .
H12 H 0.7637 0.8569 1.2666 0.059 Uiso 1 1 calc R . .
C13 C 0.7173(2) 0.6521(3) 1.27901(10) 0.0442(5) Uani 1 1 d . . .
H13 H 0.6903 0.6623 1.3262 0.053 Uiso 1 1 calc R . .
C14 C 0.71357(19) 0.5220(3) 1.24593(11) 0.0397(5) Uani 1 1 d . . .
H14 H 0.6856 0.4417 1.2706 0.048 Uiso 1 1 calc R . .
C15 C 0.75068(18) 0.5086(2) 1.17657(10) 0.0316(4) Uani 1 1 d . . .
H15 H 0.7468 0.4191 1.1534 0.038 Uiso 1 1 calc R . .
C16 C 0.95812(15) 0.74202(17) 0.90405(8) 0.0207(3) Uani 1 1 d . . .
H16 H 1.0478 0.7628 0.9123 0.025 Uiso 1 1 calc R . .
P2 P 0.56958(4) 0.38013(4) 0.58414(2) 0.01820(8) Uani 1 1 d . . .
O7 O 0.70008(10) 0.31898(13) 0.57468(6) 0.0227(2) Uani 1 1 d . . .
O8 O 0.57490(10) 0.46098(13) 0.65800(6) 0.0213(2) Uani 1 1 d . . .
O9 O 0.47207(11) 0.27360(13) 0.57671(6) 0.0244(2) Uani 1 1 d . . .
O10 O 0.64067(11) 0.61407(13) 0.52623(7) 0.0252(3) Uani 1 1 d . . .
H10 H 0.6241 0.6864 0.5011 0.038 Uiso 1 1 calc R . .
O11 O 0.62129(12) 0.43950(16) 0.40471(7) 0.0324(3) Uani 1 1 d . . .
O12 O 0.42023(12) 0.41757(14) 0.42040(6) 0.0285(3) Uani 1 1 d . . .
C17 C 0.91084(15) 0.80317(18) 0.83120(8) 0.0215(3) Uani 1 1 d . . .
C18 C 0.9251(2) 1.0015(2) 0.75525(10) 0.0340(4) Uani 1 1 d . . .
H18A H 0.9663 1.0934 0.7550 0.051 Uiso 1 1 calc R . .
H18B H 0.8360 1.0154 0.7504 0.051 Uiso 1 1 calc R . .
H18C H 0.9499 0.9444 0.7148 0.051 Uiso 1 1 calc R . .
C19 C 0.79716(15) 0.47966(19) 0.66497(9) 0.0241(3) Uani 1 1 d . . .
H19A H 0.7899 0.5627 0.6325 0.029 Uiso 1 1 calc R . .
H19B H 0.8709 0.4930 0.6986 0.029 Uiso 1 1 calc R . .
C20 C 0.81319(14) 0.34846(18) 0.62042(9) 0.0232(3) Uani 1 1 d . . .
H20 H 0.8290 0.2671 0.6542 0.028 Uiso 1 1 calc R . .
C21 C 0.91877(15) 0.3593(2) 0.57331(9) 0.0271(4) Uani 1 1 d . . .
C22 C 0.90995(19) 0.4370(3) 0.51013(11) 0.0378(4) Uani 1 1 d . . .
H22 H 0.8354 0.4836 0.4950 0.045 Uiso 1 1 calc R . .
C23 C 1.0106(2) 0.4469(3) 0.46874(12) 0.0444(5) Uani 1 1 d . . .
H23 H 1.0043 0.4994 0.4250 0.053 Uiso 1 1 calc R . .
C24 C 1.1187(2) 0.3815(3) 0.49069(13) 0.0492(6) Uani 1 1 d . . .
H24 H 1.1863 0.3859 0.4614 0.059 Uiso 1 1 calc R . .
C25 C 1.1294(2) 0.3108(3) 0.55395(15) 0.0536(6) Uani 1 1 d . . .
H25 H 1.2056 0.2692 0.5702 0.064 Uiso 1 1 calc R . .
C26 C 1.02946(19) 0.2985(3) 0.59534(12) 0.0430(5) Uani 1 1 d . . .
H26 H 1.0376 0.2473 0.6395 0.052 Uiso 1 1 calc R . .
C27 C 0.68452(15) 0.47151(17) 0.70796(8) 0.0212(3) Uani 1 1 d . . .
H27 H 0.6791 0.5620 0.7353 0.025 Uiso 1 1 calc R . .
C28 C 0.68752(15) 0.35167(17) 0.76229(8) 0.0216(3) Uani 1 1 d . . .
C29 C 0.78272(18) 0.3513(2) 0.81691(10) 0.0323(4) Uani 1 1 d . . .
H29 H 0.8417 0.4251 0.8196 0.039 Uiso 1 1 calc R . .
C30 C 0.79079(19) 0.2429(3) 0.86715(10) 0.0378(5) Uani 1 1 d . . .
H30 H 0.8565 0.2419 0.9037 0.045 Uiso 1 1 calc R . .
C31 C 0.70483(19) 0.1371(2) 0.86465(10) 0.0356(4) Uani 1 1 d . . .
H31 H 0.7111 0.0629 0.8992 0.043 Uiso 1 1 calc R . .
C32 C 0.60926(19) 0.1390(2) 0.81172(10) 0.0345(4) Uani 1 1 d . . .
H32 H 0.5489 0.0666 0.8103 0.041 Uiso 1 1 calc R . .
C33 C 0.60050(17) 0.2462(2) 0.76032(9) 0.0283(4) Uani 1 1 d . . .
H33 H 0.5346 0.2467 0.7239 0.034 Uiso 1 1 calc R . .
C34 C 0.54395(15) 0.51687(17) 0.51630(9) 0.0200(3) Uani 1 1 d . . .
H34 H 0.4651 0.5662 0.5242 0.024 Uiso 1 1 calc R . .
C35 C 0.53505(15) 0.45376(17) 0.44079(8) 0.0218(3) Uani 1 1 d . . .
C36 C 0.4027(2) 0.3538(2) 0.34916(10) 0.0384(5) Uani 1 1 d . . .
H36A H 0.3157 0.3306 0.3387 0.058 Uiso 1 1 calc R . .
H36B H 0.4519 0.2675 0.3479 0.058 Uiso 1 1 calc R . .
H36C H 0.4285 0.4204 0.3128 0.058 Uiso 1 1 calc R . .
Cl1 Cl 0.30858(5) 0.58733(6) 0.63986(3) 0.04219(13) Uani 1 1 d . . .
Cl2 Cl 0.07976(6) 0.68734(7) 0.69051(4) 0.05988(18) Uani 1 1 d . . .
C37 C 0.17428(19) 0.6853(3) 0.61801(13) 0.0433(5) Uani 1 1 d . . .
H37A H 0.1965 0.7834 0.6058 0.052 Uiso 1 1 calc R . .
H37B H 0.1289 0.6434 0.5750 0.052 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 0.01827(17) 0.01754(17) 0.01832(17) 0.00070(15) 0.00166(13) -0.00176(15)
O1 0.0180(5) 0.0245(6) 0.0261(6) 0.0053(5) 0.0004(4) -0.0025(5)
O2 0.0221(5) 0.0269(6) 0.0203(5) 0.0043(5) -0.0009(4) -0.0031(5)
O3 0.0275(6) 0.0215(5) 0.0256(6) -0.0017(5) 0.0034(5) -0.0043(5)
O4 0.0372(7) 0.0185(6) 0.0265(6) -0.0015(5) -0.0017(5) 0.0015(5)
O5 0.0402(8) 0.0382(7) 0.0236(6) 0.0012(5) -0.0056(5) -0.0104(6)
O6 0.0348(7) 0.0270(6) 0.0253(6) 0.0061(5) 0.0000(5) -0.0052(5)
C1 0.0273(8) 0.0214(7) 0.0239(8) 0.0006(6) 0.0041(6) -0.0055(6)
C2 0.0190(7) 0.0256(8) 0.0221(8) -0.0001(6) 0.0042(6) -0.0046(6)
C3 0.0209(8) 0.0299(9) 0.0290(9) -0.0005(7) -0.0003(6) -0.0032(7)
C4 0.0245(9) 0.0631(14) 0.0353(10) 0.0163(10) 0.0040(7) -0.0037(9)
C5 0.0213(9) 0.0611(15) 0.0663(15) 0.0218(13) -0.0024(9) -0.0096(10)
C6 0.0327(11) 0.0498(14) 0.0662(16) -0.0032(12) -0.0203(10) -0.0086(10)
C7 0.0431(13) 0.106(2) 0.0445(13) -0.0257(15) -0.0087(10) -0.0105(15)
C8 0.0294(10) 0.100(2) 0.0343(11) -0.0216(13) 0.0017(8) -0.0107(12)
C9 0.0257(8) 0.0198(7) 0.0212(7) 0.0037(6) 0.0063(6) 0.0004(6)
C10 0.0226(8) 0.0293(9) 0.0192(7) 0.0041(6) 0.0042(6) 0.0063(6)
C11 0.0541(12) 0.0309(9) 0.0258(9) 0.0014(8) 0.0052(8) 0.0083(9)
C12 0.0683(16) 0.0493(13) 0.0297(10) -0.0104(9) 0.0080(10) 0.0181(12)
C13 0.0394(11) 0.0736(16) 0.0206(9) 0.0041(10) 0.0081(8) 0.0152(11)
C14 0.0330(10) 0.0593(14) 0.0277(10) 0.0134(9) 0.0089(8) 0.0008(10)
C15 0.0304(9) 0.0360(10) 0.0292(9) 0.0078(8) 0.0075(7) 0.0013(8)
C16 0.0223(7) 0.0207(7) 0.0191(7) -0.0001(6) 0.0017(6) -0.0007(6)
P2 0.01914(18) 0.01869(17) 0.01678(17) 0.00064(15) 0.00137(14) -0.00045(15)
O7 0.0206(5) 0.0230(5) 0.0245(5) -0.0042(5) 0.0011(4) 0.0031(5)
O8 0.0189(5) 0.0261(6) 0.0188(5) -0.0017(4) 0.0002(4) 0.0024(5)
O9 0.0254(6) 0.0256(6) 0.0217(6) 0.0027(5) -0.0009(4) -0.0060(5)
O10 0.0277(6) 0.0188(6) 0.0288(6) 0.0053(5) -0.0004(5) -0.0046(5)
O11 0.0313(7) 0.0428(8) 0.0241(6) 0.0010(6) 0.0095(5) 0.0053(6)
O12 0.0286(6) 0.0367(7) 0.0199(6) -0.0016(5) 0.0001(5) -0.0061(5)
C17 0.0210(7) 0.0253(8) 0.0185(7) -0.0001(6) 0.0040(5) 0.0008(6)
C18 0.0438(11) 0.0323(10) 0.0264(9) 0.0118(7) 0.0048(8) 0.0037(8)
C19 0.0224(8) 0.0273(8) 0.0226(8) -0.0002(6) 0.0021(6) -0.0034(6)
C20 0.0181(7) 0.0274(8) 0.0240(7) 0.0019(6) 0.0000(6) 0.0022(6)
C21 0.0218(8) 0.0318(9) 0.0281(8) -0.0025(7) 0.0046(6) 0.0022(7)
C22 0.0283(9) 0.0510(12) 0.0347(10) 0.0040(9) 0.0069(7) 0.0025(9)
C23 0.0393(11) 0.0595(14) 0.0361(11) 0.0013(10) 0.0150(9) -0.0020(11)
C24 0.0291(10) 0.0705(16) 0.0504(13) -0.0086(13) 0.0183(9) -0.0003(11)
C25 0.0269(10) 0.0741(17) 0.0608(15) 0.0047(14) 0.0113(9) 0.0146(12)
C26 0.0310(10) 0.0549(14) 0.0442(11) 0.0071(10) 0.0091(8) 0.0116(10)
C27 0.0224(7) 0.0226(7) 0.0181(7) -0.0031(6) -0.0011(6) -0.0021(6)
C28 0.0221(7) 0.0262(8) 0.0167(7) -0.0008(6) 0.0025(5) 0.0027(6)
C29 0.0296(9) 0.0396(11) 0.0267(8) -0.0049(7) -0.0044(7) 0.0000(8)
C30 0.0352(10) 0.0553(13) 0.0220(8) 0.0029(8) -0.0033(7) 0.0117(9)
C31 0.0415(11) 0.0411(11) 0.0252(9) 0.0093(8) 0.0096(7) 0.0174(9)
C32 0.0363(10) 0.0356(10) 0.0322(9) 0.0067(8) 0.0071(8) -0.0036(8)
C33 0.0252(8) 0.0360(9) 0.0235(8) 0.0035(7) 0.0007(6) -0.0036(7)
C34 0.0194(7) 0.0209(7) 0.0197(7) 0.0018(6) 0.0017(6) 0.0002(6)
C35 0.0245(8) 0.0216(7) 0.0194(7) 0.0041(6) 0.0026(6) 0.0020(6)
C36 0.0494(12) 0.0446(12) 0.0200(8) -0.0042(8) -0.0058(8) -0.0069(9)
Cl1 0.0325(2) 0.0511(3) 0.0442(3) 0.0058(2) 0.0107(2) 0.0085(2)
Cl2 0.0407(3) 0.0590(4) 0.0835(5) -0.0207(3) 0.0286(3) -0.0031(3)
C37 0.0302(10) 0.0452(12) 0.0549(14) 0.0011(10) 0.0073(9) 0.0063(9)

_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 1.4647(13) . ?
P1 O2 1.5607(12) . ?
P1 O1 1.5652(11) . ?
P1 C16 1.8321(16) . ?
O1 C2 1.4628(19) . ?
O2 C9 1.456(2) . ?
O4 C16 1.402(2) . ?
O4 H40 0.8400 . ?
O5 C17 1.192(2) . ?
O6 C17 1.324(2) . ?
O6 C18 1.447(2) . ?
C1 C2 1.514(2) . ?
C1 C9 1.527(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.501(2) . ?
C2 H2 1.0000 . ?
C3 C8 1.375(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.514(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.370(3) . ?
C10 C15 1.386(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.525(2) . ?
C16 H16 1.0000 . ?
P2 O9 1.4664(12) . ?
P2 O7 1.5608(12) . ?
P2 O8 1.5670(12) . ?
P2 C34 1.8131(16) . ?
O7 C20 1.4725(19) . ?
O8 C27 1.4619(19) . ?
O10 C34 1.403(2) . ?
O10 H10 0.8400 . ?
O11 C35 1.203(2) . ?
O12 C35 1.328(2) . ?
O12 C36 1.453(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.510(2) . ?
C19 C27 1.518(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.502(2) . ?
C20 H20 1.0000 . ?
C21 C26 1.374(3) . ?
C21 C22 1.381(3) . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.368(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.349(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.517(2) . ?
C27 H27 1.0000 . ?
C28 C33 1.378(2) . ?
C28 C29 1.397(2) . ?
C29 C30 1.385(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.372(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.379(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.519(2) . ?
C34 H34 1.0000 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Cl1 C37 1.758(2) . ?
Cl2 C37 1.756(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?

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 O2 112.16(7) . . ?
O3 P1 O1 113.96(7) . . ?
O2 P1 O1 107.19(6) . . ?
O3 P1 C16 111.73(7) . . ?
O2 P1 C16 105.72(7) . . ?
O1 P1 C16 105.50(7) . . ?
C2 O1 P1 122.55(10) . . ?
C9 O2 P1 127.27(10) . . ?
C16 O4 H40 109.5 . . ?
C17 O6 C18 116.75(14) . . ?
C2 C1 C9 111.94(14) . . ?
C2 C1 H1A 109.2 . . ?
C9 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C9 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
O1 C2 C3 107.92(13) . . ?
O1 C2 C1 108.74(13) . . ?
C3 C2 C1 111.91(14) . . ?
O1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C8 C3 C4 119.23(18) . . ?
C8 C3 C2 121.89(16) . . ?
C4 C3 C2 118.73(17) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 120.5(2) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
O2 C9 C10 108.84(13) . . ?
O2 C9 C1 110.93(13) . . ?
C10 C9 C1 112.53(14) . . ?
O2 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C1 C9 H9 108.1 . . ?
C11 C10 C15 119.73(17) . . ?
C11 C10 C9 123.14(16) . . ?
C15 C10 C9 117.12(16) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.82(18) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O4 C16 C17 108.22(13) . . ?
O4 C16 P1 111.02(11) . . ?
C17 C16 P1 110.85(11) . . ?
O4 C16 H16 108.9 . . ?
C17 C16 H16 108.9 . . ?
P1 C16 H16 108.9 . . ?
O9 P2 O7 113.40(7) . . ?
O9 P2 O8 113.44(7) . . ?
O7 P2 O8 107.78(6) . . ?
O9 P2 C34 110.67(7) . . ?
O7 P2 C34 106.38(7) . . ?
O8 P2 C34 104.56(7) . . ?
C20 O7 P2 126.79(10) . . ?
C27 O8 P2 124.25(10) . . ?
C34 O10 H10 109.5 . . ?
C35 O12 C36 115.11(14) . . ?
O5 C17 O6 125.51(16) . . ?
O5 C17 C16 124.69(16) . . ?
O6 C17 C16 109.80(14) . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C27 112.18(14) . . ?
C20 C19 H19A 109.2 . . ?
C27 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C27 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
O7 C20 C21 108.99(13) . . ?
O7 C20 C19 110.18(13) . . ?
C21 C20 C19 112.83(14) . . ?
O7 C20 H20 108.2 . . ?
C21 C20 H20 108.2 . . ?
C19 C20 H20 108.2 . . ?
C26 C21 C22 118.68(18) . . ?
C26 C21 C20 119.71(17) . . ?
C22 C21 C20 121.47(16) . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 120.02(19) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 120.8(2) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
O8 C27 C28 110.25(13) . . ?
O8 C27 C19 109.16(12) . . ?
C28 C27 C19 114.15(14) . . ?
O8 C27 H27 107.7 . . ?
C28 C27 H27 107.7 . . ?
C19 C27 H27 107.7 . . ?
C33 C28 C29 119.49(16) . . ?
C33 C28 C27 122.99(14) . . ?
C29 C28 C27 117.51(15) . . ?
C30 C29 C28 119.78(19) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 120.66(18) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 119.63(18) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C31 C32 C33 120.48(19) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C28 C33 C32 119.94(17) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
O10 C34 C35 112.01(13) . . ?
O10 C34 P2 107.58(11) . . ?
C35 C34 P2 110.77(11) . . ?
O10 C34 H34 108.8 . . ?
C35 C34 H34 108.8 . . ?
P2 C34 H34 108.8 . . ?
O11 C35 O12 125.08(16) . . ?
O11 C35 C34 123.93(15) . . ?
O12 C35 C34 110.99(13) . . ?
O12 C36 H36A 109.5 . . ?
O12 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O12 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl2 C37 Cl1 110.95(13) . . ?
Cl2 C37 H37A 109.4 . . ?
Cl1 C37 H37A 109.4 . . ?
Cl2 C37 H37B 109.4 . . ?
Cl1 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?

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 C2 -124.02(12) . . . . ?
O2 P1 O1 C2 0.71(14) . . . . ?
C16 P1 O1 C2 113.05(13) . . . . ?
O3 P1 O2 C9 146.43(13) . . . . ?
O1 P1 O2 C9 20.62(14) . . . . ?
C16 P1 O2 C9 -91.57(14) . . . . ?
P1 O1 C2 C3 -162.24(12) . . . . ?
P1 O1 C2 C1 -40.65(17) . . . . ?
C9 C1 C2 O1 64.71(17) . . . . ?
C9 C1 C2 C3 -176.17(14) . . . . ?
O1 C2 C3 C8 38.3(3) . . . . ?
C1 C2 C3 C8 -81.3(3) . . . . ?
O1 C2 C3 C4 -146.18(18) . . . . ?
C1 C2 C3 C4 94.2(2) . . . . ?
C8 C3 C4 C5 2.9(4) . . . . ?
C2 C3 C4 C5 -172.8(2) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C4 C3 C8 C7 -2.6(4) . . . . ?
C2 C3 C8 C7 172.9(3) . . . . ?
C6 C7 C8 C3 1.7(5) . . . . ?
P1 O2 C9 C10 -122.56(13) . . . . ?
P1 O2 C9 C1 1.76(19) . . . . ?
C2 C1 C9 O2 -45.74(18) . . . . ?
C2 C1 C9 C10 76.46(17) . . . . ?
O2 C9 C10 C11 17.3(2) . . . . ?
C1 C9 C10 C11 -106.1(2) . . . . ?
O2 C9 C10 C15 -163.82(15) . . . . ?
C1 C9 C10 C15 72.8(2) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 178.4(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 C10 1.0(3) . . . . ?
C11 C10 C15 C14 -0.1(3) . . . . ?
C9 C10 C15 C14 -179.10(17) . . . . ?
O3 P1 C16 O4 165.42(11) . . . . ?
O2 P1 C16 O4 43.14(13) . . . . ?
O1 P1 C16 O4 -70.23(12) . . . . ?
O3 P1 C16 C17 -74.27(13) . . . . ?
O2 P1 C16 C17 163.45(11) . . . . ?
O1 P1 C16 C17 50.08(12) . . . . ?
O9 P2 O7 C20 -134.96(13) . . . . ?
O8 P2 O7 C20 -8.52(15) . . . . ?
C34 P2 O7 C20 103.16(14) . . . . ?
O9 P2 O8 C27 125.24(12) . . . . ?
O7 P2 O8 C27 -1.17(14) . . . . ?
C34 P2 O8 C27 -114.08(13) . . . . ?
C18 O6 C17 O5 -1.1(3) . . . . ?
C18 O6 C17 C16 179.03(14) . . . . ?
O4 C16 C17 O5 20.3(2) . . . . ?
P1 C16 C17 O5 -101.68(18) . . . . ?
O4 C16 C17 O6 -159.85(14) . . . . ?
P1 C16 C17 O6 78.19(15) . . . . ?
P2 O7 C20 C21 -141.54(12) . . . . ?
P2 O7 C20 C19 -17.23(19) . . . . ?
C27 C19 C20 O7 53.62(18) . . . . ?
C27 C19 C20 C21 175.69(14) . . . . ?
O7 C20 C21 C26 -138.25(19) . . . . ?
C19 C20 C21 C26 99.0(2) . . . . ?
O7 C20 C21 C22 46.0(2) . . . . ?
C19 C20 C21 C22 -76.7(2) . . . . ?
C26 C21 C22 C23 2.9(3) . . . . ?
C20 C21 C22 C23 178.64(19) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 C25 -2.2(4) . . . . ?
C23 C24 C25 C26 3.0(4) . . . . ?
C22 C21 C26 C25 -2.1(4) . . . . ?
C20 C21 C26 C25 -177.9(2) . . . . ?
C24 C25 C26 C21 -0.8(4) . . . . ?
P2 O8 C27 C28 -91.32(14) . . . . ?
P2 O8 C27 C19 34.83(18) . . . . ?
C20 C19 C27 O8 -62.48(17) . . . . ?
C20 C19 C27 C28 61.39(18) . . . . ?
O8 C27 C28 C33 3.1(2) . . . . ?
C19 C27 C28 C33 -120.22(18) . . . . ?
O8 C27 C28 C29 -176.05(14) . . . . ?
C19 C27 C28 C29 60.66(19) . . . . ?
C33 C28 C29 C30 1.9(3) . . . . ?
C27 C28 C29 C30 -178.93(17) . . . . ?
C28 C29 C30 C31 -1.2(3) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C30 C31 C32 C33 1.0(3) . . . . ?
C29 C28 C33 C32 -1.2(3) . . . . ?
C27 C28 C33 C32 179.69(16) . . . . ?
C31 C32 C33 C28 -0.2(3) . . . . ?
O9 P2 C34 O10 -179.56(10) . . . . ?
O7 P2 C34 O10 -55.96(12) . . . . ?
O8 P2 C34 O10 57.94(12) . . . . ?
O9 P2 C34 C35 -56.82(13) . . . . ?
O7 P2 C34 C35 66.78(12) . . . . ?
O8 P2 C34 C35 -179.32(10) . . . . ?
C36 O12 C35 O11 1.2(3) . . . . ?
C36 O12 C35 C34 -179.01(14) . . . . ?
O10 C34 C35 O11 28.6(2) . . . . ?
P2 C34 C35 O11 -91.57(18) . . . . ?
O10 C34 C35 O12 -151.21(13) . . . . ?
P2 C34 C35 O12 88.67(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.11
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 952038'