# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1027592'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 O3 P'
_chemical_formula_weight         418.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   18.332(4)
_cell_length_b                   6.1364(12)
_cell_length_c                   20.639(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.621(3)
_cell_angle_gamma                90.00
_cell_volume                     2212.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5245
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.18

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15575
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4318
_reflns_number_gt                3598
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0945P)²+0.3118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4318
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.29808(3) 0.77496(8) 1.06536(2) 0.02857(18) Uani 1 1 d . . .
O2 O 0.42029(8) 0.7289(2) 0.93768(7) 0.0356(3) Uani 1 1 d . . .
O3 O 0.54254(8) 0.7340(2) 0.99780(8) 0.0423(4) Uani 1 1 d . . .
O1 O 0.29120(8) 0.5364(2) 1.07027(7) 0.0410(4) Uani 1 1 d . . .
C2 C 0.36263(10) 0.8513(3) 1.01837(8) 0.0278(4) Uani 1 1 d . . .
H2 H 0.3611 1.0095 1.0116 0.033 Uiso 1 1 calc R . .
C3 C 0.28960(11) 0.8440(3) 0.89057(9) 0.0303(4) Uani 1 1 d . . .
C4 C 0.33878(10) 0.8996(3) 1.14686(9) 0.0309(4) Uani 1 1 d . . .
C5 C 0.20759(11) 0.8976(3) 1.02133(9) 0.0311(4) Uani 1 1 d . . .
C6 C 0.34580(11) 0.7358(3) 0.94985(9) 0.0306(4) Uani 1 1 d . . .
H6 H 0.3287 0.5866 0.9542 0.037 Uiso 1 1 calc R . .
C7 C 0.47683(12) 0.7457(3) 0.99608(10) 0.0331(5) Uani 1 1 d . . .
C8 C 0.30450(12) 1.0448(3) 0.86727(10) 0.0379(5) Uani 1 1 d . . .
H8 H 0.3492 1.1185 0.8901 0.045 Uiso 1 1 calc R . .
C9 C 0.17074(12) 0.8394(4) 0.80199(11) 0.0436(5) Uani 1 1 d . . .
H9 H 0.1244 0.7702 0.7815 0.052 Uiso 1 1 calc R . .
C27 C 0.44441(11) 0.7792(3) 1.05392(10) 0.0327(4) Uani 1 1 d . . .
H27A H 0.4725 0.8908 1.0848 0.039 Uiso 1 1 calc R . .
H27B H 0.4454 0.6451 1.0790 0.039 Uiso 1 1 calc R . .
C10 C 0.12951(12) 1.1348(4) 0.71278(10) 0.0402(5) Uani 1 1 d . . .
C11 C 0.18609(11) 1.0349(3) 0.77567(9) 0.0336(4) Uani 1 1 d . . .
C12 C 0.25383(12) 1.1372(3) 0.81059(10) 0.0381(5) Uani 1 1 d . . .
H12 H 0.2654 1.2716 0.7954 0.046 Uiso 1 1 calc R . .
C13 C 0.19975(12) 1.1083(4) 0.99630(10) 0.0405(5) Uani 1 1 d . . .
H13 H 0.2420 1.2001 1.0056 0.049 Uiso 1 1 calc R . .
C14 C 0.12902(14) 1.1811(4) 0.95762(13) 0.0529(6) Uani 1 1 d . . .
H14 H 0.1238 1.3214 0.9397 0.063 Uiso 1 1 calc R . .
C15 C 0.22210(12) 0.7437(3) 0.85777(10) 0.0396(5) Uani 1 1 d . . .
H15 H 0.2106 0.6095 0.8732 0.048 Uiso 1 1 calc R . .
C16 C 0.36922(12) 1.1067(4) 1.15501(11) 0.0426(5) Uani 1 1 d . . .
H16 H 0.3651 1.1941 1.1173 0.051 Uiso 1 1 calc R . .
C17 C 0.14403(12) 0.7650(4) 1.00884(12) 0.0432(5) Uani 1 1 d . . .
H17 H 0.1489 0.6235 1.0258 0.052 Uiso 1 1 calc R . .
C18 C 0.34381(13) 0.7710(4) 1.20292(11) 0.0443(5) Uani 1 1 d . . .
H18 H 0.3228 0.6318 1.1973 0.053 Uiso 1 1 calc R . .
C19 C 0.40592(14) 1.1840(4) 1.21962(13) 0.0550(7) Uani 1 1 d . . .
H19 H 0.4272 1.3229 1.2256 0.066 Uiso 1 1 calc R . .
C20 C 0.07350(13) 0.8420(5) 0.97141(14) 0.0594(7) Uani 1 1 d . . .
H20 H 0.0305 0.7535 0.9638 0.071 Uiso 1 1 calc R . .
C21 C 0.41070(14) 1.0534(5) 1.27494(11) 0.0598(7) Uani 1 1 d . . .
H21 H 0.4353 1.1051 1.3184 0.072 Uiso 1 1 calc R . .
C22 C 0.06733(16) 1.2485(5) 0.73447(15) 0.0618(7) Uani 1 1 d . . .
H22A H 0.0298 1.3069 0.6952 0.093 Uiso 1 1 calc R . .
H22B H 0.0895 1.3647 0.7653 0.093 Uiso 1 1 calc R . .
H22C H 0.0434 1.1459 0.7567 0.093 Uiso 1 1 calc R . .
C23 C 0.37984(16) 0.8490(5) 1.26691(12) 0.0616(7) Uani 1 1 d . . .
H23 H 0.3832 0.7628 1.3048 0.074 Uiso 1 1 calc R . .
C24 C 0.06630(14) 1.0483(5) 0.94533(13) 0.0594(7) Uani 1 1 d . . .
H24 H 0.0186 1.0987 0.9192 0.071 Uiso 1 1 calc R . .
C25 C 0.0926(2) 0.9565(5) 0.66220(13) 0.0783(10) Uani 1 1 d . . .
H25A H 0.0593 1.0214 0.6217 0.117 Uiso 1 1 calc R . .
H25B H 0.0635 0.8617 0.6820 0.117 Uiso 1 1 calc R . .
H25C H 0.1316 0.8741 0.6511 0.117 Uiso 1 1 calc R . .
C26 C 0.16728(16) 1.2972(6) 0.67811(15) 0.0741(9) Uani 1 1 d . . .
H26A H 0.2079 1.2269 0.6658 0.111 Uiso 1 1 calc R . .
H26B H 0.1877 1.4156 0.7086 0.111 Uiso 1 1 calc R . .
H26C H 0.1302 1.3521 0.6380 0.111 Uiso 1 1 calc R . .


_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 1.4753(15) . ?
P1 C4 1.7920(19) . ?
P1 C5 1.798(2) . ?
P1 C2 1.8042(19) . ?
O2 C7 1.335(2) . ?
O2 C6 1.462(2) . ?
O3 C7 1.196(2) . ?
C2 C27 1.522(3) . ?
C2 C6 1.528(2) . ?
C3 C15 1.364(3) . ?
C3 C8 1.380(3) . ?
C3 C6 1.495(3) . ?
C4 C16 1.378(3) . ?
C4 C18 1.380(3) . ?
C5 C17 1.380(3) . ?
C5 C13 1.384(3) . ?
C7 C27 1.500(3) . ?
C8 C12 1.376(3) . ?
C9 C15 1.378(3) . ?
C9 C11 1.381(3) . ?
C10 C26 1.511(3) . ?
C10 C22 1.515(3) . ?
C10 C25 1.522(3) . ?
C10 C11 1.523(3) . ?
C11 C12 1.383(3) . ?
C13 C14 1.375(3) . ?
C14 C24 1.369(4) . ?
C16 C19 1.383(3) . ?
C17 C20 1.374(3) . ?
C18 C23 1.372(3) . ?
C19 C21 1.376(4) . ?
C20 C24 1.366(4) . ?
C21 C23 1.365(4) . ?

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 C4 112.27(9) . . ?
O1 P1 C5 111.42(9) . . ?
C4 P1 C5 110.74(9) . . ?
O1 P1 C2 112.22(9) . . ?
C4 P1 C2 103.84(9) . . ?
C5 P1 C2 105.93(9) . . ?
C7 O2 C6 110.67(15) . . ?
C27 C2 C6 101.82(15) . . ?
C27 C2 P1 112.09(13) . . ?
C6 C2 P1 113.30(13) . . ?
C15 C3 C8 118.38(18) . . ?
C15 C3 C6 120.18(18) . . ?
C8 C3 C6 121.44(17) . . ?
C16 C4 C18 120.22(19) . . ?
C16 C4 P1 123.12(15) . . ?
C18 C4 P1 116.49(17) . . ?
C17 C5 C13 119.66(19) . . ?
C17 C5 P1 116.44(16) . . ?
C13 C5 P1 123.76(15) . . ?
O2 C6 C3 108.68(15) . . ?
O2 C6 C2 103.59(14) . . ?
C3 C6 C2 116.58(16) . . ?
O3 C7 O2 121.45(19) . . ?
O3 C7 C27 128.50(19) . . ?
O2 C7 C27 110.05(17) . . ?
C12 C8 C3 120.66(19) . . ?
C15 C9 C11 122.0(2) . . ?
C7 C27 C2 103.07(15) . . ?
C26 C10 C22 109.3(2) . . ?
C26 C10 C25 108.8(2) . . ?
C22 C10 C25 108.4(2) . . ?
C26 C10 C11 112.16(18) . . ?
C22 C10 C11 108.22(18) . . ?
C25 C10 C11 110.00(19) . . ?
C9 C11 C12 116.53(18) . . ?
C9 C11 C10 121.17(18) . . ?
C12 C11 C10 122.26(18) . . ?
C8 C12 C11 121.65(19) . . ?
C14 C13 C5 119.6(2) . . ?
C24 C14 C13 120.4(2) . . ?
C3 C15 C9 120.66(19) . . ?
C4 C16 C19 119.7(2) . . ?
C20 C17 C5 120.0(2) . . ?
C23 C18 C4 119.9(2) . . ?
C21 C19 C16 119.4(2) . . ?
C24 C20 C17 120.2(2) . . ?
C23 C21 C19 120.9(2) . . ?
C21 C23 C18 119.9(2) . . ?
C14 C24 C20 120.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.059
