# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_41208a
_database_code_depnum_ccdc_archive 'CCDC 1040645'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 O3 P'
_chemical_formula_weight         288.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.826(4)
_cell_length_b                   17.749(10)
_cell_length_c                   14.404(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.154(9)
_cell_angle_gamma                90
_cell_volume                     1487.1(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    1767
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      23.61

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10019
_diffrn_reflns_av_unetI/netI     0.1127
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.416
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.896
_reflns_number_total             5774
_reflns_number_gt                3973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.777
_reflns_Friedel_fraction_full    0.799

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1005P)²+4.7285P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.07(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5774
_refine_ls_number_parameters     368
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0962
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2391
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.6280(5) 0.61376(15) 0.53129(17) 0.0282(6) Uani 1 1 d . . . . .
O1 O 0.4003(13) 0.6398(5) 0.5628(6) 0.039(2) Uani 1 1 d . . . . .
O2 O 0.8347(18) 0.7584(5) 0.6169(7) 0.058(3) Uani 1 1 d . . . . .
O3 O 1.2437(16) 0.6448(5) 0.7399(5) 0.043(2) Uani 1 1 d D . . . .
C1 C 0.8742(18) 0.6245(6) 0.6131(7) 0.030(2) Uani 1 1 d . . . . .
H1A H 0.8536 0.5907 0.6658 0.036 Uiso 1 1 calc R U . . .
H1B H 1.0116 0.6077 0.5827 0.036 Uiso 1 1 calc R U . . .
C2 C 0.917(2) 0.7014(7) 0.6498(7) 0.038(3) Uani 1 1 d . . . . .
C3 C 1.085(3) 0.7042(8) 0.7377(9) 0.055(4) Uani 1 1 d . . . . .
H3A H 0.9906 0.6972 0.7921 0.066 Uiso 1 1 calc R U . . .
C4 C 1.199(4) 0.7784(10) 0.7495(13) 0.096(7) Uani 1 1 d . . . . .
H4A H 1.2986 0.7781 0.8057 0.144 Uiso 1 1 calc R U . . .
H4B H 1.0828 0.8173 0.7543 0.144 Uiso 1 1 calc R U . . .
H4C H 1.2889 0.7886 0.6963 0.144 Uiso 1 1 calc R U . . .
C5 C 0.6235(19) 0.5139(7) 0.5119(7) 0.031(3) Uani 1 1 d . . . . .
C6 C 0.446(2) 0.4707(8) 0.5432(9) 0.047(3) Uani 1 1 d . . . . .
H6 H 0.3265 0.4944 0.5732 0.056 Uiso 1 1 calc R U . . .
C7 C 0.441(3) 0.3937(8) 0.5315(9) 0.055(4) Uani 1 1 d . . . . .
H7 H 0.3163 0.3657 0.5520 0.067 Uiso 1 1 calc R U . . .
C8 C 0.618(3) 0.3578(8) 0.4897(9) 0.048(4) Uani 1 1 d . . . . .
H8 H 0.6150 0.3053 0.4814 0.058 Uiso 1 1 calc R U . . .
C9 C 0.801(2) 0.3999(7) 0.4601(8) 0.042(3) Uani 1 1 d . . . . .
H9 H 0.9261 0.3758 0.4343 0.050 Uiso 1 1 calc R U . . .
C10 C 0.798(2) 0.4771(7) 0.4687(8) 0.038(3) Uani 1 1 d . . . . .
H10 H 0.9179 0.5055 0.4448 0.046 Uiso 1 1 calc R U . . .
C11 C 0.703(2) 0.6552(7) 0.4224(7) 0.033(2) Uani 1 1 d . . . . .
C12 C 0.537(3) 0.6501(9) 0.3498(9) 0.062(4) Uani 1 1 d . . . . .
H12 H 0.3989 0.6246 0.3587 0.075 Uiso 1 1 calc R U . . .
C13 C 0.575(3) 0.6824(10) 0.2632(9) 0.068(5) Uani 1 1 d . . . . .
H13 H 0.4605 0.6810 0.2146 0.081 Uiso 1 1 calc R U . . .
C14 C 0.789(3) 0.7174(9) 0.2510(9) 0.057(4) Uani 1 1 d . . . . .
H14 H 0.8218 0.7380 0.1931 0.069 Uiso 1 1 calc R U . . .
C15 C 0.948(3) 0.7210(9) 0.3230(10) 0.063(4) Uani 1 1 d . . . . .
H15 H 1.0888 0.7451 0.3146 0.075 Uiso 1 1 calc R U . . .
C16 C 0.908(2) 0.6904(8) 0.4087(8) 0.046(3) Uani 1 1 d . . . . .
H16 H 1.0209 0.6936 0.4576 0.055 Uiso 1 1 calc R U . . .
P2 P 0.3497(4) 0.55105(15) 0.98618(17) 0.0263(6) Uani 1 1 d . . . . .
O4 O 0.5615(12) 0.5183(5) 0.9501(5) 0.0342(18) Uani 1 1 d . . . . .
O5 O 0.1250(17) 0.4073(5) 0.9288(7) 0.055(2) Uani 1 1 d . . . . .
O6 O -0.2635(15) 0.5083(5) 0.7801(5) 0.0387(19) Uani 1 1 d . . . . .
H6A H -0.3408 0.5175 0.8254 0.058 Uiso 1 1 calc R U . . .
C17 C 0.0984(19) 0.5395(6) 0.9118(7) 0.031(2) Uani 1 1 d . . . . .
H17A H -0.0319 0.5616 0.9422 0.037 Uiso 1 1 calc R U . . .
H17B H 0.1183 0.5679 0.8545 0.037 Uiso 1 1 calc R U . . .
C18 C 0.040(2) 0.4597(6) 0.8863(8) 0.035(3) Uani 1 1 d . . . . .
C19 C -0.112(2) 0.4457(7) 0.8017(7) 0.040(3) Uani 1 1 d . . . . .
H19 H -0.2060 0.4002 0.8119 0.048 Uiso 1 1 calc R U . . .
C20 C 0.028(3) 0.4329(9) 0.7194(9) 0.076(5) Uani 1 1 d . . . . .
H20A H 0.0447 0.3792 0.7093 0.113 Uiso 1 1 calc R U . . .
H20B H 0.1785 0.4555 0.7307 0.113 Uiso 1 1 calc R U . . .
H20C H -0.0485 0.4556 0.6649 0.113 Uiso 1 1 calc R U . . .
C21 C 0.3717(19) 0.6516(6) 0.9997(7) 0.029(2) Uani 1 1 d . . . . .
C22 C 0.558(3) 0.6866(8) 0.9712(11) 0.056(4) Uani 1 1 d . . . . .
H22 H 0.6712 0.6577 0.9436 0.067 Uiso 1 1 calc R U . . .
C23 C 0.593(3) 0.7650(9) 0.9804(13) 0.072(5) Uani 1 1 d . . . . .
H23 H 0.7282 0.7875 0.9609 0.087 Uiso 1 1 calc R U . . .
C24 C 0.430(3) 0.8067(8) 1.0175(9) 0.054(4) Uani 1 1 d . . . . .
H24 H 0.4521 0.8588 1.0252 0.065 Uiso 1 1 calc R U . . .
C25 C 0.232(3) 0.7741(9) 1.0444(12) 0.066(5) Uani 1 1 d . . . . .
H25 H 0.1139 0.8033 1.0682 0.079 Uiso 1 1 calc R U . . .
C26 C 0.210(3) 0.6944(8) 1.0350(11) 0.054(4) Uani 1 1 d . . . . .
H26 H 0.0759 0.6711 1.0545 0.065 Uiso 1 1 calc R U . . .
C27 C 0.299(2) 0.5155(6) 1.1007(7) 0.030(2) Uani 1 1 d . . . . .
C28 C 0.466(2) 0.4738(7) 1.1460(8) 0.046(3) Uani 1 1 d . . . . .
H28 H 0.6057 0.4642 1.1185 0.055 Uiso 1 1 calc R U . . .
C29 C 0.427(3) 0.4460(9) 1.2333(10) 0.065(4) Uani 1 1 d . . . . .
H29 H 0.5396 0.4153 1.2631 0.078 Uiso 1 1 calc R U . . .
C30 C 0.239(3) 0.4605(8) 1.2766(9) 0.055(4) Uani 1 1 d . . . . .
H30 H 0.2237 0.4435 1.3377 0.066 Uiso 1 1 calc R U . . .
C31 C 0.066(3) 0.5010(11) 1.2311(10) 0.070(5) Uani 1 1 d . . . . .
H31 H -0.0716 0.5104 1.2603 0.084 Uiso 1 1 calc R U . . .
C32 C 0.094(2) 0.5276(9) 1.1431(9) 0.063(4) Uani 1 1 d . . . . .
H32 H -0.0254 0.5542 1.1114 0.076 Uiso 1 1 calc R U . . .
H3 H 1.380(16) 0.640(8) 0.707(8) 0.06(4) Uiso 1 1 d D . . . .


_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 1.499(7) . ?
P1 C5 1.795(13) . ?
P1 C11 1.808(11) . ?
P1 C1 1.815(11) . ?
O2 C2 1.206(15) . ?
O3 C3 1.400(17) . ?
O3 H3 0.95(6) . ?
C1 C2 1.480(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.560(17) . ?
C3 C4 1.48(2) . ?
C3 H3A 0.9900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 C6 1.382(16) . ?
C5 C10 1.386(16) . ?
C6 C7 1.38(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.38(2) . ?
C7 H7 0.9400 . ?
C8 C9 1.387(19) . ?
C8 H8 0.9400 . ?
C9 C10 1.376(18) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C16 1.370(16) . ?
C11 C12 1.386(17) . ?
C12 C13 1.401(19) . ?
C12 H12 0.9400 . ?
C13 C14 1.42(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.35(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.380(17) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
P2 O4 1.484(7) . ?
P2 C17 1.777(11) . ?
P2 C21 1.800(12) . ?
P2 C27 1.805(10) . ?
O5 C18 1.206(14) . ?
O6 C19 1.442(15) . ?
O6 H6A 0.8300 . ?
C17 C18 1.497(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.487(16) . ?
C19 C20 1.493(17) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C26 1.332(17) . ?
C21 C22 1.335(17) . ?
C22 C23 1.41(2) . ?
C22 H22 0.9400 . ?
C23 C24 1.34(2) . ?
C23 H23 0.9400 . ?
C24 C25 1.37(2) . ?
C24 H24 0.9400 . ?
C25 C26 1.43(2) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C28 1.359(16) . ?
C27 C32 1.386(18) . ?
C28 C29 1.382(18) . ?
C28 H28 0.9400 . ?
C29 C30 1.31(2) . ?
C29 H29 0.9400 . ?
C30 C31 1.38(2) . ?
C30 H30 0.9400 . ?
C31 C32 1.371(18) . ?
C31 H31 0.9400 . ?
C32 H32 0.9400 . ?

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 C5 110.3(5) . . ?
O1 P1 C11 113.4(5) . . ?
C5 P1 C11 105.6(5) . . ?
O1 P1 C1 116.9(5) . . ?
C5 P1 C1 102.1(5) . . ?
C11 P1 C1 107.5(5) . . ?
C3 O3 H3 128(9) . . ?
C2 C1 P1 116.1(8) . . ?
C2 C1 H1A 108.3 . . ?
P1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
P1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
O2 C2 C1 125.3(11) . . ?
O2 C2 C3 120.8(11) . . ?
C1 C2 C3 113.9(10) . . ?
O3 C3 C4 112.3(14) . . ?
O3 C3 C2 112.2(10) . . ?
C4 C3 C2 112.2(12) . . ?
O3 C3 H3A 106.5 . . ?
C4 C3 H3A 106.5 . . ?
C2 C3 H3A 106.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 117.8(12) . . ?
C6 C5 P1 120.1(10) . . ?
C10 C5 P1 122.0(9) . . ?
C7 C6 C5 121.6(13) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 119.9(13) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 119.4(13) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.8(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 121.4(11) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C16 C11 C12 119.8(12) . . ?
C16 C11 P1 124.4(8) . . ?
C12 C11 P1 115.9(10) . . ?
C11 C12 C13 120.6(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 118.1(13) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C15 C14 C13 119.8(12) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.7(13) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 120.0(12) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O4 P2 C17 114.6(5) . . ?
O4 P2 C21 111.7(5) . . ?
C17 P2 C21 103.4(5) . . ?
O4 P2 C27 111.3(5) . . ?
C17 P2 C27 109.9(5) . . ?
C21 P2 C27 105.2(5) . . ?
C19 O6 H6A 109.5 . . ?
C18 C17 P2 115.2(8) . . ?
C18 C17 H17A 108.5 . . ?
P2 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
P2 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
O5 C18 C19 119.8(11) . . ?
O5 C18 C17 121.5(10) . . ?
C19 C18 C17 118.5(9) . . ?
O6 C19 C18 112.2(9) . . ?
O6 C19 C20 107.5(10) . . ?
C18 C19 C20 110.4(12) . . ?
O6 C19 H19 108.9 . . ?
C18 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
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 . . ?
C26 C21 C22 117.2(13) . . ?
C26 C21 P2 124.0(10) . . ?
C22 C21 P2 118.8(10) . . ?
C21 C22 C23 123.0(14) . . ?
C21 C22 H22 118.5 . . ?
C23 C22 H22 118.5 . . ?
C24 C23 C22 118.7(15) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 120.6(14) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 117.7(14) . . ?
C24 C25 H25 121.1 . . ?
C26 C25 H25 121.1 . . ?
C21 C26 C25 122.7(14) . . ?
C21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C28 C27 C32 118.8(10) . . ?
C28 C27 P2 118.8(9) . . ?
C32 C27 P2 122.4(9) . . ?
C27 C28 C29 118.8(13) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C30 C29 C28 123.1(14) . . ?
C30 C29 H29 118.4 . . ?
C28 C29 H29 118.4 . . ?
C29 C30 C31 119.0(12) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C32 C31 C30 119.8(14) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C27 120.3(13) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 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 C1 C2 -55.2(9) . . . . ?
C5 P1 C1 C2 -175.6(8) . . . . ?
C11 P1 C1 C2 73.6(9) . . . . ?
P1 C1 C2 O2 -15.9(16) . . . . ?
P1 C1 C2 C3 164.6(9) . . . . ?
O2 C2 C3 O3 -150.8(12) . . . . ?
C1 C2 C3 O3 28.7(15) . . . . ?
O2 C2 C3 C4 -23(2) . . . . ?
C1 C2 C3 C4 156.3(14) . . . . ?
O1 P1 C5 C6 -12.7(11) . . . . ?
C11 P1 C5 C6 -135.6(10) . . . . ?
C1 P1 C5 C6 112.2(10) . . . . ?
O1 P1 C5 C10 169.7(9) . . . . ?
C11 P1 C5 C10 46.8(11) . . . . ?
C1 P1 C5 C10 -65.5(10) . . . . ?
C10 C5 C6 C7 -0.6(19) . . . . ?
P1 C5 C6 C7 -178.3(11) . . . . ?
C5 C6 C7 C8 2(2) . . . . ?
C6 C7 C8 C9 0(2) . . . . ?
C7 C8 C9 C10 -3(2) . . . . ?
C8 C9 C10 C5 4.2(19) . . . . ?
C6 C5 C10 C9 -2.3(18) . . . . ?
P1 C5 C10 C9 175.4(10) . . . . ?
O1 P1 C11 C16 128.5(11) . . . . ?
C5 P1 C11 C16 -110.7(12) . . . . ?
C1 P1 C11 C16 -2.3(13) . . . . ?
O1 P1 C11 C12 -51.4(12) . . . . ?
C5 P1 C11 C12 69.4(11) . . . . ?
C1 P1 C11 C12 177.8(10) . . . . ?
C16 C11 C12 C13 -2(2) . . . . ?
P1 C11 C12 C13 178.0(13) . . . . ?
C11 C12 C13 C14 3(2) . . . . ?
C12 C13 C14 C15 -2(2) . . . . ?
C13 C14 C15 C16 1(3) . . . . ?
C12 C11 C16 C15 1(2) . . . . ?
P1 C11 C16 C15 -179.3(11) . . . . ?
C14 C15 C16 C11 0(2) . . . . ?
O4 P2 C17 C18 56.8(9) . . . . ?
C21 P2 C17 C18 178.6(8) . . . . ?
C27 P2 C17 C18 -69.5(9) . . . . ?
P2 C17 C18 O5 15.7(15) . . . . ?
P2 C17 C18 C19 -159.2(9) . . . . ?
O5 C18 C19 O6 158.3(11) . . . . ?
C17 C18 C19 O6 -26.7(14) . . . . ?
O5 C18 C19 C20 -81.8(15) . . . . ?
C17 C18 C19 C20 93.1(13) . . . . ?
O4 P2 C21 C26 -176.7(11) . . . . ?
C17 P2 C21 C26 59.5(12) . . . . ?
C27 P2 C21 C26 -55.8(12) . . . . ?
O4 P2 C21 C22 4.8(12) . . . . ?
C17 P2 C21 C22 -119.0(11) . . . . ?
C27 P2 C21 C22 125.7(11) . . . . ?
C26 C21 C22 C23 3(2) . . . . ?
P2 C21 C22 C23 -178.8(13) . . . . ?
C21 C22 C23 C24 -2(3) . . . . ?
C22 C23 C24 C25 -1(3) . . . . ?
C23 C24 C25 C26 3(3) . . . . ?
C22 C21 C26 C25 -1(2) . . . . ?
P2 C21 C26 C25 -179.6(13) . . . . ?
C24 C25 C26 C21 -1(3) . . . . ?
O4 P2 C27 C28 9.3(12) . . . . ?
C17 P2 C27 C28 137.4(10) . . . . ?
C21 P2 C27 C28 -111.9(10) . . . . ?
O4 P2 C27 C32 -169.2(11) . . . . ?
C17 P2 C27 C32 -41.1(13) . . . . ?
C21 P2 C27 C32 69.6(12) . . . . ?
C32 C27 C28 C29 -1(2) . . . . ?
P2 C27 C28 C29 -179.4(11) . . . . ?
C27 C28 C29 C30 -3(2) . . . . ?
C28 C29 C30 C31 5(3) . . . . ?
C29 C30 C31 C32 -2(3) . . . . ?
C30 C31 C32 C27 -2(3) . . . . ?
C28 C27 C32 C31 3(2) . . . . ?
P2 C27 C32 C31 -178.4(13) . . . . ?

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
O6 H6A O4 0.83 1.91 2.710(10) 160.5 1_455
O3 H3 O1 0.95(6) 2.09(11) 2.757(11) 126(10) 1_655

_refine_diff_density_max         1.148
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.111

_shelxl_version_number           2013-2



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_41128b
_database_code_depnum_ccdc_archive 'CCDC 1040646'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 O3 P'
_chemical_formula_weight         288.26

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.8589(19)
_cell_length_b                   17.826(5)
_cell_length_c                   14.463(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.258(5)
_cell_angle_gamma                90
_cell_volume                     1508.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3831
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.23

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9387
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.410
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.868
_reflns_number_total             5122
_reflns_number_gt                4610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.738
_reflns_Friedel_fraction_full    0.746

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0886P)²+3.9873P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1791 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.07(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5122
_refine_ls_number_parameters     365
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.2087
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.6507(3) 0.05945(11) 0.51362(13) 0.0253(5) Uani 1 1 d . . . . .
O1 O 0.4382(9) 0.0923(4) 0.5501(4) 0.0356(14) Uani 1 1 d . . . . .
O2 O 0.8770(13) 0.2032(4) 0.5717(5) 0.0563(19) Uani 1 1 d . . . . .
O3 O 1.2646(11) 0.1023(4) 0.7203(4) 0.0410(15) Uani 1 1 d . . . . .
H3 H 1.3817 0.1054 0.6908 0.061 Uiso 1 1 calc R U . . .
C1 C 0.9026(13) 0.0711(5) 0.5889(5) 0.0278(17) Uani 1 1 d . . . . .
H1A H 0.8822 0.0432 0.6462 0.033 Uiso 1 1 calc R U . . .
H1B H 1.0325 0.0488 0.5591 0.033 Uiso 1 1 calc R U . . .
C2 C 0.9598(14) 0.1507(5) 0.6132(6) 0.0311(18) Uani 1 1 d . . . . .
C3 C 1.1180(17) 0.1640(5) 0.6974(6) 0.039(2) Uani 1 1 d . . . . .
H3A H 1.2118 0.2092 0.6873 0.046 Uiso 1 1 calc R U . . .
C4 C 0.973(3) 0.1769(7) 0.7809(7) 0.079(5) Uani 1 1 d . . . . .
H4A H 0.8982 0.1304 0.7963 0.119 Uiso 1 1 calc R U . . .
H4B H 0.8593 0.2150 0.7659 0.119 Uiso 1 1 calc R U . . .
H4C H 1.0713 0.1933 0.8334 0.119 Uiso 1 1 calc R U . . .
C5 C 0.7007(15) 0.0965(5) 0.4009(5) 0.0315(18) Uani 1 1 d . . . . .
C6 C 0.5356(16) 0.1368(6) 0.3532(6) 0.042(2) Uani 1 1 d . . . . .
H6 H 0.3947 0.1454 0.3793 0.050 Uiso 1 1 calc R U . . .
C7 C 0.573(2) 0.1649(7) 0.2674(8) 0.063(3) Uani 1 1 d . . . . .
H7 H 0.4613 0.1957 0.2378 0.076 Uiso 1 1 calc R U . . .
C8 C 0.764(2) 0.1500(8) 0.2240(7) 0.061(3) Uani 1 1 d . . . . .
H8 H 0.7817 0.1682 0.1638 0.073 Uiso 1 1 calc R U . . .
C9 C 0.930(2) 0.1087(9) 0.2674(8) 0.074(4) Uani 1 1 d . . . . .
H9 H 1.0637 0.0973 0.2372 0.089 Uiso 1 1 calc R U . . .
C10 C 0.9039(16) 0.0827(8) 0.3581(7) 0.066(4) Uani 1 1 d . . . . .
H10 H 1.0228 0.0560 0.3896 0.079 Uiso 1 1 calc R U . . .
C11 C 0.6235(14) -0.0411(5) 0.5000(5) 0.0296(18) Uani 1 1 d . . . . .
C12 C 0.4346(17) -0.0757(6) 0.5290(9) 0.052(3) Uani 1 1 d . . . . .
H12 H 0.3203 -0.0471 0.5554 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4069(19) -0.1528(7) 0.5205(9) 0.059(3) Uani 1 1 d . . . . .
H13 H 0.2744 -0.1755 0.5412 0.071 Uiso 1 1 calc R U . . .
C14 C 0.570(2) -0.1960(6) 0.4823(8) 0.053(3) Uani 1 1 d . . . . .
H14 H 0.5485 -0.2479 0.4744 0.064 Uiso 1 1 calc R U . . .
C15 C 0.766(2) -0.1620(7) 0.4557(9) 0.062(3) Uani 1 1 d . . . . .
H15 H 0.8838 -0.1910 0.4320 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7914(18) -0.0845(7) 0.4637(8) 0.054(3) Uani 1 1 d . . . . .
H16 H 0.9246 -0.0615 0.4441 0.065 Uiso 1 1 calc R U . . .
P2 P 0.3717(3) 0.99689(12) 0.96868(13) 0.0273(5) Uani 1 1 d . . . . .
O4 O 0.5969(11) 0.9701(4) 0.9358(4) 0.0413(16) Uani 1 1 d . . . . .
O5 O 0.1660(14) 0.8525(4) 0.8837(6) 0.057(2) Uani 1 1 d . . . . .
O6 O -0.2414(11) 0.9657(4) 0.7610(4) 0.0429(16) Uani 1 1 d . . . . .
H6A H -0.3005 0.9689 0.8117 0.064 Uiso 1 1 calc R U . . .
C17 C 0.1292(13) 0.9870(5) 0.8866(5) 0.0308(17) Uani 1 1 d . . . . .
H17A H -0.0074 1.0045 0.9162 0.037 Uiso 1 1 calc R U . . .
H17B H 0.1523 1.0202 0.8339 0.037 Uiso 1 1 calc R U . . .
C18 C 0.0824(16) 0.9088(6) 0.8496(6) 0.039(2) Uani 1 1 d . . . . .
C19 C -0.0851(19) 0.9066(6) 0.7637(7) 0.050(3) Uani 1 1 d . . . . .
H19 H 0.0089 0.9136 0.7096 0.060 Uiso 1 1 calc R U . . .
C20 C -0.196(3) 0.8329(8) 0.7510(11) 0.107(7) Uani 1 1 d . U . . .
H20A H -0.2851 0.8220 0.8040 0.161 Uiso 1 1 calc R U . . .
H20B H -0.0802 0.7945 0.7456 0.161 Uiso 1 1 calc R U . . .
H20C H -0.2960 0.8336 0.6952 0.161 Uiso 1 1 calc R U . . .
C21 C 0.3784(14) 1.0959(6) 0.9890(5) 0.032(2) Uani 1 1 d . . . . .
C22 C 0.5526(17) 1.1397(6) 0.9567(7) 0.046(2) Uani 1 1 d . . . . .
H22 H 0.6715 1.1164 0.9266 0.055 Uiso 1 1 calc R U . . .
C23 C 0.556(2) 1.2173(7) 0.9675(8) 0.054(3) Uani 1 1 d . . . . .
H23 H 0.6771 1.2456 0.9454 0.065 Uiso 1 1 calc R U . . .
C24 C 0.384(2) 1.2519(7) 1.0105(7) 0.049(3) Uani 1 1 d . . . . .
H24 H 0.3905 1.3040 1.0205 0.059 Uiso 1 1 calc R U . . .
C25 C 0.2007(18) 1.2115(6) 1.0396(6) 0.045(2) Uani 1 1 d . . . . .
H25 H 0.0768 1.2360 1.0650 0.054 Uiso 1 1 calc R U . . .
C26 C 0.2018(16) 1.1333(6) 1.0307(6) 0.038(2) Uani 1 1 d . . . . .
H26 H 0.0808 1.1054 1.0533 0.045 Uiso 1 1 calc R U . . .
C27 C 0.2956(14) 0.9554(5) 1.0770(6) 0.0343(19) Uani 1 1 d . . . . .
C28 C 0.461(2) 0.9599(7) 1.1494(7) 0.062(3) Uani 1 1 d . . . . .
H28 H 0.6003 0.9839 1.1402 0.074 Uiso 1 1 calc R U . . .
C29 C 0.421(2) 0.9289(9) 1.2362(7) 0.074(4) Uani 1 1 d . . . . .
H29 H 0.5325 0.9320 1.2855 0.088 Uiso 1 1 calc R U . . .
C30 C 0.212(2) 0.8934(7) 1.2479(7) 0.063(3) Uani 1 1 d . . . . .
H30 H 0.1822 0.8728 1.3057 0.076 Uiso 1 1 calc R U . . .
C31 C 0.054(2) 0.8886(7) 1.1770(8) 0.063(3) Uani 1 1 d . . . . .
H31 H -0.0839 0.8634 1.1855 0.076 Uiso 1 1 calc R U . . .
C32 C 0.0919(17) 0.9203(7) 1.0914(7) 0.051(3) Uani 1 1 d . . . . .
H32 H -0.0225 0.9177 1.0432 0.061 Uiso 1 1 calc R U . . .


_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 1.499(6) . ?
P1 C1 1.795(8) . ?
P1 C5 1.798(8) . ?
P1 C11 1.808(9) . ?
O2 C2 1.199(11) . ?
O3 C3 1.423(11) . ?
C1 C2 1.496(11) . ?
C2 C3 1.506(12) . ?
C3 C4 1.532(14) . ?
C5 C6 1.361(12) . ?
C5 C10 1.395(13) . ?
C6 C7 1.368(15) . ?
C7 C8 1.338(17) . ?
C8 C9 1.347(17) . ?
C9 C10 1.408(14) . ?
C11 C12 1.355(13) . ?
C11 C16 1.379(13) . ?
C12 C13 1.387(16) . ?
C13 C14 1.369(17) . ?
C14 C15 1.374(16) . ?
C15 C16 1.392(17) . ?
P2 O4 1.505(6) . ?
P2 C21 1.789(10) . ?
P2 C17 1.808(8) . ?
P2 C27 1.811(9) . ?
O5 C18 1.210(12) . ?
O6 C19 1.395(13) . ?
C17 C18 1.512(13) . ?
C18 C19 1.540(12) . ?
C19 C20 1.473(17) . ?
C21 C22 1.388(13) . ?
C21 C26 1.397(12) . ?
C22 C23 1.391(16) . ?
C23 C24 1.363(16) . ?
C24 C25 1.380(15) . ?
C25 C26 1.399(14) . ?
C27 C32 1.374(13) . ?
C27 C28 1.386(13) . ?
C28 C29 1.404(15) . ?
C29 C30 1.395(18) . ?
C30 C31 1.345(17) . ?
C31 C32 1.390(14) . ?

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 C1 114.3(4) . . ?
O1 P1 C5 110.9(4) . . ?
C1 P1 C5 109.7(4) . . ?
O1 P1 C11 110.8(4) . . ?
C1 P1 C11 104.1(4) . . ?
C5 P1 C11 106.5(4) . . ?
C2 C1 P1 114.7(6) . . ?
O2 C2 C1 122.9(8) . . ?
O2 C2 C3 119.6(8) . . ?
C1 C2 C3 117.3(7) . . ?
O3 C3 C2 113.7(7) . . ?
O3 C3 C4 106.6(8) . . ?
C2 C3 C4 108.5(9) . . ?
C6 C5 C10 117.9(8) . . ?
C6 C5 P1 120.4(7) . . ?
C10 C5 P1 121.7(7) . . ?
C5 C6 C7 120.4(10) . . ?
C8 C7 C6 122.4(10) . . ?
C7 C8 C9 119.3(10) . . ?
C8 C9 C10 120.0(11) . . ?
C5 C10 C9 119.8(10) . . ?
C12 C11 C16 118.3(9) . . ?
C12 C11 P1 119.1(7) . . ?
C16 C11 P1 122.5(7) . . ?
C11 C12 C13 121.1(10) . . ?
C14 C13 C12 120.8(10) . . ?
C13 C14 C15 118.7(10) . . ?
C14 C15 C16 120.0(10) . . ?
C11 C16 C15 121.0(10) . . ?
O4 P2 C21 110.7(4) . . ?
O4 P2 C17 115.6(4) . . ?
C21 P2 C17 102.3(4) . . ?
O4 P2 C27 114.0(4) . . ?
C21 P2 C27 105.4(4) . . ?
C17 P2 C27 107.8(4) . . ?
C18 C17 P2 116.2(6) . . ?
O5 C18 C17 124.1(8) . . ?
O5 C18 C19 122.2(9) . . ?
C17 C18 C19 113.8(8) . . ?
O6 C19 C20 112.7(11) . . ?
O6 C19 C18 113.0(8) . . ?
C20 C19 C18 112.3(9) . . ?
C22 C21 C26 116.9(9) . . ?
C22 C21 P2 120.7(7) . . ?
C26 C21 P2 122.2(7) . . ?
C21 C22 C23 122.0(10) . . ?
C24 C23 C22 119.6(10) . . ?
C23 C24 C25 120.8(11) . . ?
C24 C25 C26 119.0(10) . . ?
C21 C26 C25 121.6(9) . . ?
C32 C27 C28 119.1(9) . . ?
C32 C27 P2 125.2(7) . . ?
C28 C27 P2 115.7(8) . . ?
C27 C28 C29 120.6(12) . . ?
C30 C29 C28 118.5(11) . . ?
C31 C30 C29 120.5(9) . . ?
C30 C31 C32 121.0(11) . . ?
C27 C32 C31 120.2(10) . . ?

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 C1 C2 -57.4(7) . . . . ?
C5 P1 C1 C2 67.9(7) . . . . ?
C11 P1 C1 C2 -178.5(6) . . . . ?
P1 C1 C2 O2 -15.3(11) . . . . ?
P1 C1 C2 C3 161.0(6) . . . . ?
O2 C2 C3 O3 -158.9(8) . . . . ?
C1 C2 C3 O3 24.7(10) . . . . ?
O2 C2 C3 C4 82.7(11) . . . . ?
C1 C2 C3 C4 -93.7(10) . . . . ?
O1 P1 C5 C6 -11.8(9) . . . . ?
C1 P1 C5 C6 -139.0(8) . . . . ?
C11 P1 C5 C6 108.9(8) . . . . ?
O1 P1 C5 C10 170.9(9) . . . . ?
C1 P1 C5 C10 43.7(10) . . . . ?
C11 P1 C5 C10 -68.4(10) . . . . ?
C10 C5 C6 C7 -2.4(16) . . . . ?
P1 C5 C6 C7 -179.8(9) . . . . ?
C5 C6 C7 C8 4.8(19) . . . . ?
C6 C7 C8 C9 -3(2) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C6 C5 C10 C9 -1.4(18) . . . . ?
P1 C5 C10 C9 175.9(10) . . . . ?
C8 C9 C10 C5 3(2) . . . . ?
O1 P1 C11 C12 -4.9(9) . . . . ?
C1 P1 C11 C12 118.5(8) . . . . ?
C5 P1 C11 C12 -125.6(8) . . . . ?
O1 P1 C11 C16 177.1(8) . . . . ?
C1 P1 C11 C16 -59.5(9) . . . . ?
C5 P1 C11 C16 56.4(9) . . . . ?
C16 C11 C12 C13 -1.6(17) . . . . ?
P1 C11 C12 C13 -179.7(9) . . . . ?
C11 C12 C13 C14 -0.1(19) . . . . ?
C12 C13 C14 C15 2.4(19) . . . . ?
C13 C14 C15 C16 -3(2) . . . . ?
C12 C11 C16 C15 0.9(17) . . . . ?
P1 C11 C16 C15 178.9(10) . . . . ?
C14 C15 C16 C11 1(2) . . . . ?
O4 P2 C17 C18 56.1(7) . . . . ?
C21 P2 C17 C18 176.6(6) . . . . ?
C27 P2 C17 C18 -72.7(7) . . . . ?
P2 C17 C18 O5 14.7(12) . . . . ?
P2 C17 C18 C19 -165.8(7) . . . . ?
O5 C18 C19 O6 150.8(10) . . . . ?
C17 C18 C19 O6 -28.8(12) . . . . ?
O5 C18 C19 C20 22.0(16) . . . . ?
C17 C18 C19 C20 -157.6(12) . . . . ?
O4 P2 C21 C22 13.5(9) . . . . ?
C17 P2 C21 C22 -110.2(8) . . . . ?
C27 P2 C21 C22 137.2(8) . . . . ?
O4 P2 C21 C26 -171.9(7) . . . . ?
C17 P2 C21 C26 64.4(8) . . . . ?
C27 P2 C21 C26 -48.2(8) . . . . ?
C26 C21 C22 C23 2.0(15) . . . . ?
P2 C21 C22 C23 176.8(9) . . . . ?
C21 C22 C23 C24 -0.5(18) . . . . ?
C22 C23 C24 C25 -3.0(18) . . . . ?
C23 C24 C25 C26 4.8(16) . . . . ?
C22 C21 C26 C25 -0.1(14) . . . . ?
P2 C21 C26 C25 -174.9(8) . . . . ?
C24 C25 C26 C21 -3.2(15) . . . . ?
O4 P2 C27 C32 -127.4(9) . . . . ?
C21 P2 C27 C32 111.0(10) . . . . ?
C17 P2 C27 C32 2.3(11) . . . . ?
O4 P2 C27 C28 52.1(10) . . . . ?
C21 P2 C27 C28 -69.5(9) . . . . ?
C17 P2 C27 C28 -178.2(8) . . . . ?
C32 C27 C28 C29 0.2(19) . . . . ?
P2 C27 C28 C29 -179.4(11) . . . . ?
C27 C28 C29 C30 0(2) . . . . ?
C28 C29 C30 C31 1(2) . . . . ?
C29 C30 C31 C32 -2(2) . . . . ?
C28 C27 C32 C31 -1.2(17) . . . . ?
P2 C27 C32 C31 178.3(9) . . . . ?
C30 C31 C32 C27 2(2) . . . . ?

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
O3 H3 O1 0.83 2.09 2.721(8) 132.3 1_655
C1 H1A O6 0.98 2.31 3.267(10) 166.1 1_645
O6 H6A O4 0.83 1.93 2.751(8) 172.7 1_455
C17 H17B O3 0.98 2.32 3.295(10) 170.9 1_465

_refine_diff_density_max         0.892
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-2



