# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_kck189
_database_code_depnum_ccdc_archive 'CCDC 1409420'
_audit_update_record             
;
2015-06-29 deposited with the CCDC.
2016-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H25 O5 P'
_chemical_formula_sum            'C24 H25 O5 P'
_chemical_formula_weight         424.41

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   'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.381(3)
_cell_length_b                   13.319(2)
_cell_length_c                   18.156(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4203.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2463
_cell_measurement_theta_min      3.2590
_cell_measurement_theta_max      28.2240

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10958
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3694
_reflns_number_gt                2540
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'Bruker SHELXTL'
_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 > 2σ(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)+(0.0666P)²+0.5779P] 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         3694
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.10599(4) 0.38237(5) 0.19619(4) 0.0418(2) Uani 1 1 d . . .
O5 O 0.08205(10) 0.49121(14) 0.21676(9) 0.0468(5) Uani 1 1 d . . .
O4 O 0.18408(9) 0.39225(13) 0.15409(10) 0.0491(5) Uani 1 1 d . . .
C13 C 0.03801(12) 0.33985(17) 0.12765(12) 0.0333(5) Uani 1 1 d . . .
H13 H 0.0448 0.3831 0.0845 0.040 Uiso 1 1 calc R . .
C10 C 0.09263(13) 0.10970(19) 0.01134(13) 0.0370(6) Uani 1 1 d . . .
O3 O 0.11192(11) 0.31937(15) 0.26068(9) 0.0618(6) Uani 1 1 d . . .
C21 C 0.18401(14) 0.5756(2) 0.14760(13) 0.0441(6) Uani 1 1 d . . .
C3 C 0.04730(13) 0.1557(2) 0.15429(13) 0.0406(6) Uani 1 1 d . . .
H3 H 0.0326 0.1709 0.2023 0.049 Uiso 1 1 calc R . .
C1 C 0.07884(12) 0.21073(18) 0.03262(12) 0.0337(5) Uani 1 1 d . . .
C2 C 0.05622(12) 0.23390(18) 0.10323(12) 0.0327(5) Uani 1 1 d . . .
O2 O 0.15527(10) 0.30050(15) -0.04892(9) 0.0567(5) Uani 1 1 d . . .
C14 C -0.04560(13) 0.34831(17) 0.15028(12) 0.0338(5) Uani 1 1 d . . .
C22 C 0.10062(15) 0.5752(2) 0.16986(15) 0.0497(7) Uani 1 1 d . . .
H22A H 0.0889 0.6372 0.1956 0.060 Uiso 1 1 calc R . .
H22B H 0.0688 0.5726 0.1260 0.060 Uiso 1 1 calc R . .
C9 C 0.08280(13) 0.03351(19) 0.06389(14) 0.0414(6) Uani 1 1 d . . .
C15 C -0.07091(16) 0.3444(2) 0.22226(13) 0.0476(7) Uani 1 1 d . . .
H15 H -0.0355 0.3396 0.2605 0.057 Uiso 1 1 calc R . .
C8 C 0.11302(14) 0.0818(2) -0.06117(15) 0.0478(7) Uani 1 1 d . . .
H8 H 0.1184 0.1310 -0.0972 0.057 Uiso 1 1 calc R . .
C4 C 0.05940(14) 0.0600(2) 0.13564(14) 0.0461(6) Uani 1 1 d . . .
H4 H 0.0522 0.0098 0.1706 0.055 Uiso 1 1 calc R . .
C5 C 0.09527(15) -0.0668(2) 0.04271(17) 0.0549(7) Uani 1 1 d . . .
H5 H 0.0886 -0.1178 0.0771 0.066 Uiso 1 1 calc R . .
O1 O 0.03221(12) 0.3382(2) -0.04630(11) 0.0846(8) Uani 1 1 d . . .
C20 C 0.20025(16) 0.4780(2) 0.10870(15) 0.0553(8) Uani 1 1 d . . .
H20A H 0.1692 0.4743 0.0644 0.066 Uiso 1 1 calc R . .
H20B H 0.2539 0.4764 0.0941 0.066 Uiso 1 1 calc R . .
C11 C 0.08453(15) 0.2899(2) -0.02438(13) 0.0426(6) Uani 1 1 d . . .
C16 C -0.14814(16) 0.3477(2) 0.23765(15) 0.0569(8) Uani 1 1 d . . .
H16 H -0.1644 0.3464 0.2864 0.068 Uiso 1 1 calc R . .
C19 C -0.09994(14) 0.3554(2) 0.09568(14) 0.0474(7) Uani 1 1 d . . .
H19 H -0.0843 0.3595 0.0468 0.057 Uiso 1 1 calc R . .
C17 C -0.20114(16) 0.3527(2) 0.18300(16) 0.0546(7) Uani 1 1 d . . .
H17 H -0.2534 0.3534 0.1940 0.065 Uiso 1 1 calc R . .
C6 C 0.11673(16) -0.0901(2) -0.0266(2) 0.0640(9) Uani 1 1 d . . .
H6 H 0.1261 -0.1566 -0.0393 0.077 Uiso 1 1 calc R . .
C7 C 0.12475(16) -0.0156(2) -0.07869(17) 0.0602(8) Uani 1 1 d . . .
H7 H 0.1384 -0.0325 -0.1266 0.072 Uiso 1 1 calc R . .
C24 C 0.23554(16) 0.5874(2) 0.21481(15) 0.0574(8) Uani 1 1 d . . .
H24A H 0.2238 0.6495 0.2392 0.086 Uiso 1 1 calc R . .
H24B H 0.2884 0.5876 0.1996 0.086 Uiso 1 1 calc R . .
H24C H 0.2269 0.5325 0.2481 0.086 Uiso 1 1 calc R . .
C18 C -0.17675(15) 0.3567(2) 0.11198(16) 0.0582(8) Uani 1 1 d . . .
H18 H -0.2126 0.3603 0.0741 0.070 Uiso 1 1 calc R . .
C23 C 0.1981(2) 0.6614(2) 0.09456(16) 0.0733(9) Uani 1 1 d . . .
H23A H 0.1879 0.7240 0.1189 0.110 Uiso 1 1 calc R . .
H23B H 0.1646 0.6546 0.0528 0.110 Uiso 1 1 calc R . .
H23C H 0.2506 0.6600 0.0784 0.110 Uiso 1 1 calc R . .
C12 C 0.1663(2) 0.3666(3) -0.11064(17) 0.0827(11) Uani 1 1 d . . .
H12A H 0.2199 0.3686 -0.1234 0.124 Uiso 1 1 calc R . .
H12B H 0.1492 0.4329 -0.0978 0.124 Uiso 1 1 calc R . .
H12C H 0.1372 0.3425 -0.1519 0.124 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.4442(19) . ?
P1 O5 1.5536(19) . ?
P1 O4 1.5632(18) . ?
P1 C13 1.807(2) . ?
O5 C22 1.443(3) . ?
O4 C20 1.436(3) . ?
C13 C14 1.515(3) . ?
C13 C2 1.513(3) . ?
C10 C9 1.403(3) . ?
C10 C8 1.413(3) . ?
C10 C1 1.420(3) . ?
C21 C22 1.505(3) . ?
C21 C20 1.507(4) . ?
C21 C23 1.514(4) . ?
C21 C24 1.522(3) . ?
C3 C4 1.336(3) . ?
C3 C2 1.403(3) . ?
C1 C2 1.376(3) . ?
C1 C11 1.481(3) . ?
O2 C11 1.315(3) . ?
O2 C12 1.438(3) . ?
C14 C19 1.373(3) . ?
C14 C15 1.380(3) . ?
C9 C4 1.409(3) . ?
C9 C5 1.407(4) . ?
C15 C16 1.372(4) . ?
C8 C7 1.351(4) . ?
C5 C6 1.349(4) . ?
O1 C11 1.183(3) . ?
C16 C17 1.356(4) . ?
C19 C18 1.368(3) . ?
C17 C18 1.358(4) . ?
C6 C7 1.378(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
O3 P1 O5 111.50(11) . . ?
O3 P1 O4 112.54(11) . . ?
O5 P1 O4 105.76(10) . . ?
O3 P1 C13 115.01(11) . . ?
O5 P1 C13 106.43(10) . . ?
O4 P1 C13 104.91(10) . . ?
C22 O5 P1 121.47(15) . . ?
C20 O4 P1 121.17(16) . . ?
C14 C13 C2 110.47(18) . . ?
C14 C13 P1 114.66(15) . . ?
C2 C13 P1 110.95(15) . . ?
C9 C10 C8 118.3(2) . . ?
C9 C10 C1 118.7(2) . . ?
C8 C10 C1 123.0(2) . . ?
C22 C21 C20 107.7(2) . . ?
C22 C21 C23 109.2(2) . . ?
C20 C21 C23 108.8(2) . . ?
C22 C21 C24 110.6(2) . . ?
C20 C21 C24 110.8(2) . . ?
C23 C21 C24 109.7(2) . . ?
C4 C3 C2 121.6(2) . . ?
C2 C1 C10 120.9(2) . . ?
C2 C1 C11 120.7(2) . . ?
C10 C1 C11 118.3(2) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 C13 122.8(2) . . ?
C3 C2 C13 118.4(2) . . ?
C11 O2 C12 117.0(2) . . ?
C19 C14 C15 117.9(2) . . ?
C19 C14 C13 118.0(2) . . ?
C15 C14 C13 124.1(2) . . ?
O5 C22 C21 112.1(2) . . ?
C10 C9 C4 118.9(2) . . ?
C10 C9 C5 118.8(2) . . ?
C4 C9 C5 122.3(3) . . ?
C16 C15 C14 120.2(2) . . ?
C7 C8 C10 120.6(3) . . ?
C3 C4 C9 121.2(2) . . ?
C6 C5 C9 121.1(3) . . ?
O4 C20 C21 112.4(2) . . ?
O1 C11 O2 123.1(2) . . ?
O1 C11 C1 124.8(2) . . ?
O2 C11 C1 112.1(2) . . ?
C17 C16 C15 121.2(2) . . ?
C18 C19 C14 121.1(2) . . ?
C16 C17 C18 119.0(3) . . ?
C5 C6 C7 120.1(3) . . ?
C8 C7 C6 121.0(3) . . ?
C17 C18 C19 120.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
