# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 892006'
loop_
_audit_author_name
_audit_author_address
'Majid Motevalli'
;Queen Mary University of London
United Kingdom
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 O6 P'
_chemical_formula_weight         326.27

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.6014(10)
_cell_length_b                   8.812(2)
_cell_length_c                   11.132(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.12(2)
_cell_angle_gamma                90
_cell_volume                     1572.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.96
_cell_measurement_theta_max      13.62

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
        Number of psi-scan sets used was   3
        Theta correction was applied.
        Averaged transmission function was used.
        No Fourier smoothing was applied.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_standards_number         2
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        2

_diffrn_reflns_number            3800
_diffrn_reflns_av_unetI/netI     0.1220
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3585
_reflns_number_gt                1836
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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     
'w=1/[σ²(Fo²)+(0.0769P)²+4.1680P] where P=(Fo²+2Fc²)/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_number_reflns         3585
_refine_ls_number_parameters     221
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.2212
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.045
_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_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
C1 C -0.2286(3) 0.5681(6) 0.3614(4) 0.0319(11) Uani 1 1 d . . . . .
C2 C -0.1864(3) 0.7137(6) 0.3748(4) 0.0300(11) Uani 1 1 d . . . . .
H2 H -0.2160 0.8012 0.3892 0.036 Uiso 1 1 calc R U . . .
C3 C -0.1075(3) 0.7304(6) 0.3677(4) 0.0257(10) Uani 1 1 d . . . . .
C4 C -0.0620(3) 0.5968(5) 0.3482(4) 0.0234(10) Uani 1 1 d . . . . .
C5 C -0.1014(2) 0.4553(5) 0.3371(4) 0.0207(10) Uani 1 1 d . . . . .
C6 C -0.0660(3) 0.8817(6) 0.3799(5) 0.0387(13) Uani 1 1 d . . . . .
H6A H -0.1043 0.9592 0.3959 0.058 Uiso 1 1 calc R U . . .
H6B H -0.0510 0.9061 0.3027 0.058 Uiso 1 1 calc R U . . .
H6C H -0.0155 0.8795 0.4492 0.058 Uiso 1 1 calc R U . . .
C7 C 0.0203(3) 0.5995(6) 0.3369(4) 0.0255(10) Uani 1 1 d . . . . .
H7 H 0.0488 0.6936 0.3414 0.031 Uiso 1 1 calc R U . . .
C8 C 0.0608(3) 0.4659(5) 0.3190(4) 0.0253(11) Uani 1 1 d . . . . .
H8 H 0.1164 0.4693 0.3113 0.030 Uiso 1 1 calc R U . . .
C9 C 0.0195(3) 0.3284(6) 0.3127(4) 0.0285(11) Uani 1 1 d . . . . .
C10 C -0.0635(2) 0.3224(6) 0.3188(4) 0.0230(10) Uani 1 1 d . . . . .
H10 H -0.0927 0.2287 0.3105 0.028 Uiso 1 1 calc R U . . .
C11 C 0.1350(3) 0.1941(6) 0.2776(5) 0.0311(12) Uani 1 1 d . . . . .
H11A H 0.1733 0.2525 0.3447 0.037 Uiso 1 1 calc R U . . .
H11B H 0.1327 0.2449 0.1975 0.037 Uiso 1 1 calc R U . . .
C12A C 0.0951(17) -0.122(4) 0.0620(18) 0.053(5) Uani 0.48(5) 1 d . U P A 1
H12A H 0.1488 -0.1016 0.0419 0.064 Uiso 0.48(5) 1 calc R U P A 1
H12B H 0.0519 -0.0554 0.0096 0.064 Uiso 0.48(5) 1 calc R U P A 1
C13A C 0.072(3) -0.281(3) 0.039(2) 0.065(7) Uani 0.50(6) 1 d . U P A 1
H13A H 0.0690 -0.3059 -0.0475 0.098 Uiso 0.50(6) 1 calc R U P A 1
H13B H 0.0173 -0.2978 0.0551 0.098 Uiso 0.50(6) 1 calc R U P A 1
H13C H 0.1137 -0.3448 0.0946 0.098 Uiso 0.50(6) 1 calc R U P A 1
C12B C 0.1177(13) -0.189(4) 0.092(2) 0.055(6) Uani 0.52(5) 1 d . U P A 2
H12C H 0.1559 -0.2726 0.1283 0.066 Uiso 0.52(5) 1 calc R U P A 2
H12D H 0.1441 -0.1282 0.0375 0.066 Uiso 0.52(5) 1 calc R U P A 2
C13B C 0.0361(18) -0.251(4) 0.017(2) 0.072(6) Uani 0.50(6) 1 d . U P A 2
H13D H 0.0457 -0.3191 -0.0471 0.108 Uiso 0.50(6) 1 calc R U P A 2
H13E H -0.0004 -0.1676 -0.0217 0.108 Uiso 0.50(6) 1 calc R U P A 2
H13F H 0.0094 -0.3078 0.0724 0.108 Uiso 0.50(6) 1 calc R U P A 2
C14 C 0.2228(3) -0.1897(7) 0.4584(5) 0.0403(13) Uani 1 1 d . . . . .
H14A H 0.2258 -0.2572 0.3886 0.048 Uiso 1 1 calc R U . . .
H14B H 0.1925 -0.2440 0.5111 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3082(4) -0.1529(8) 0.5329(5) 0.0563(17) Uani 1 1 d . . . . .
H15A H 0.3386 -0.1015 0.4801 0.084 Uiso 1 1 calc R U . . .
H15B H 0.3374 -0.2467 0.5659 0.084 Uiso 1 1 calc R U . . .
H15C H 0.3051 -0.0862 0.6020 0.084 Uiso 1 1 calc R U . . .
O1 O -0.18367(17) 0.4436(4) 0.3426(3) 0.0268(7) Uani 1 1 d . . . . .
O2 O -0.3001(2) 0.5463(5) 0.3633(3) 0.0435(10) Uani 1 1 d . . . . .
O3 O 0.05402(17) 0.1922(4) 0.2981(3) 0.0280(8) Uani 1 1 d . . . . .
O4 O 0.25341(19) 0.0031(4) 0.2389(3) 0.0363(8) Uani 1 1 d . . . . .
O5 O 0.1026(2) -0.0932(4) 0.1902(3) 0.0422(10) Uani 1 1 d . . . . .
O6 O 0.1779(2) -0.0511(4) 0.4095(3) 0.0415(10) Uani 1 1 d . . . . .
P1 P 0.17424(7) 0.00368(17) 0.27464(11) 0.0290(3) Uani 1 1 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
C1 O2 1.209(5) . ?
C1 O1 1.373(6) . ?
C1 C2 1.451(7) . ?
C2 C3 1.340(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.446(6) . ?
C3 C6 1.491(7) . ?
C4 C5 1.399(6) . ?
C4 C7 1.404(6) . ?
C5 C10 1.370(6) . ?
C5 O1 1.387(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.395(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(7) . ?
C8 H8 0.9500 . ?
C9 O3 1.357(6) . ?
C9 C10 1.398(6) . ?
C10 H10 0.9500 . ?
C11 O3 1.421(4) . ?
C11 P1 1.803(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12A O5 1.423(18) . ?
C12A C13A 1.46(4) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C12B O5 1.453(19) . ?
C12B C13B 1.50(3) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14 O6 1.461(6) . ?
C14 C15 1.479(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O4 P1 1.469(3) . ?
O5 P1 1.563(4) . ?
O6 P1 1.563(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
O2 C1 O1 116.8(5) . . ?
O2 C1 C2 126.1(5) . . ?
O1 C1 C2 117.1(4) . . ?
C3 C2 C1 123.0(4) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 C3 C4 118.5(4) . . ?
C2 C3 C6 121.9(4) . . ?
C4 C3 C6 119.7(4) . . ?
C5 C4 C7 116.8(4) . . ?
C5 C4 C3 119.2(4) . . ?
C7 C4 C3 124.0(4) . . ?
C10 C5 O1 116.0(4) . . ?
C10 C5 C4 123.6(4) . . ?
O1 C5 C4 120.4(4) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C4 C7 H7 119.5 . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
O3 C9 C8 124.1(4) . . ?
O3 C9 C10 115.1(4) . . ?
C8 C9 C10 120.8(5) . . ?
C5 C10 C9 118.1(4) . . ?
C5 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
O3 C11 P1 110.7(3) . . ?
O3 C11 H11A 109.5 . . ?
P1 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
P1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O5 C12A C13A 107.2(18) . . ?
O5 C12A H12A 110.3 . . ?
C13A C12A H12A 110.3 . . ?
O5 C12A H12B 110.3 . . ?
C13A C12A H12B 110.3 . . ?
H12A C12A H12B 108.5 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O5 C12B C13B 108.7(18) . . ?
O5 C12B H12C 109.9 . . ?
C13B C12B H12C 109.9 . . ?
O5 C12B H12D 109.9 . . ?
C13B C12B H12D 109.9 . . ?
H12C C12B H12D 108.3 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O6 C14 C15 110.3(5) . . ?
O6 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
O6 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O1 C5 121.8(4) . . ?
C9 O3 C11 117.1(4) . . ?
C12A O5 P1 123.6(9) . . ?
C12B O5 P1 121.0(7) . . ?
C14 O6 P1 120.3(3) . . ?
O4 P1 O5 115.4(2) . . ?
O4 P1 O6 116.5(2) . . ?
O5 P1 O6 104.0(2) . . ?
O4 P1 C11 111.2(2) . . ?
O5 P1 C11 107.3(2) . . ?
O6 P1 C11 101.1(2) . . ?

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
O2 C1 C2 C3 -177.7(5) . . . . ?
O1 C1 C2 C3 1.0(7) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C1 C2 C3 C6 179.1(4) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C6 C3 C4 C5 179.9(4) . . . . ?
C2 C3 C4 C7 178.8(4) . . . . ?
C6 C3 C4 C7 -1.5(7) . . . . ?
C7 C4 C5 C10 1.4(6) . . . . ?
C3 C4 C5 C10 -179.9(4) . . . . ?
C7 C4 C5 O1 -177.7(4) . . . . ?
C3 C4 C5 O1 1.1(6) . . . . ?
C5 C4 C7 C8 -1.8(6) . . . . ?
C3 C4 C7 C8 179.6(4) . . . . ?
C4 C7 C8 C9 -0.2(7) . . . . ?
C7 C8 C9 O3 -178.6(4) . . . . ?
C7 C8 C9 C10 2.7(7) . . . . ?
O1 C5 C10 C9 -179.9(4) . . . . ?
C4 C5 C10 C9 1.0(6) . . . . ?
O3 C9 C10 C5 178.1(4) . . . . ?
C8 C9 C10 C5 -3.0(6) . . . . ?
O2 C1 O1 C5 179.1(4) . . . . ?
C2 C1 O1 C5 0.3(6) . . . . ?
C10 C5 O1 C1 179.6(4) . . . . ?
C4 C5 O1 C1 -1.3(6) . . . . ?
C8 C9 O3 C11 -5.6(6) . . . . ?
C10 C9 O3 C11 173.2(4) . . . . ?
P1 C11 O3 C9 174.8(3) . . . . ?
C13A C12A O5 C12B 43(3) . . . . ?
C13A C12A O5 P1 138(2) . . . . ?
C13B C12B O5 C12A -69(3) . . . . ?
C13B C12B O5 P1 -173(2) . . . . ?
C15 C14 O6 P1 96.1(5) . . . . ?
C12A O5 P1 O4 -28.7(18) . . . . ?
C12B O5 P1 O4 6.1(19) . . . . ?
C12A O5 P1 O6 -157.5(18) . . . . ?
C12B O5 P1 O6 -122.7(19) . . . . ?
C12A O5 P1 C11 95.9(18) . . . . ?
C12B O5 P1 C11 130.6(19) . . . . ?
C14 O6 P1 O4 -46.4(4) . . . . ?
C14 O6 P1 O5 81.8(4) . . . . ?
C14 O6 P1 C11 -167.0(4) . . . . ?
O3 C11 P1 O4 173.3(3) . . . . ?
O3 C11 P1 O5 46.2(4) . . . . ?
O3 C11 P1 O6 -62.4(4) . . . . ?

_refine_diff_density_max         0.664
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 892004'
loop_
_audit_author_name
_audit_author_address
'Majid Motevalli'
;Queen Mary University of London
United Kingdom
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 Na3 O10 P'
_chemical_formula_weight         436.23

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'
Na Na 0.0362 0.0249 '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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.7973(8)
_cell_length_b                   6.4554(3)
_cell_length_c                   20.7665(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.7280(10)
_cell_angle_gamma                90
_cell_volume                     1899.72(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6092
_cell_measurement_theta_min      2,7601
_cell_measurement_theta_max      27.3910

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            24285
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.505
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4355
_reflns_number_gt                3494
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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     
'w=1/[σ²(Fo²)+(0.0410P)²+0.7365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_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
C1 C 0.21957(11) 0.7373(3) 0.43555(8) 0.0118(3) Uani 1 1 d . . . . .
C2 C 0.19359(11) 0.6951(3) 0.49528(8) 0.0126(3) Uani 1 1 d . . . . .
C3 C 0.13581(12) 0.5264(3) 0.49590(8) 0.0163(3) Uani 1 1 d . . . . .
H3 H 0.117170 0.500921 0.535303 0.020 Uiso 1 1 calc R U . . .
C4 C 0.10380(12) 0.3925(3) 0.44145(8) 0.0165(3) Uani 1 1 d . . . . .
H4 H 0.066189 0.275229 0.444031 0.020 Uiso 1 1 calc R U . . .
C5 C 0.12863(11) 0.4359(3) 0.38342(8) 0.0124(3) Uani 1 1 d . . . . .
C6 C 0.18500(11) 0.6042(3) 0.38036(8) 0.0123(3) Uani 1 1 d . . . . .
H6 H 0.200788 0.630554 0.339906 0.015 Uiso 1 1 calc R U . . .
C7 C 0.06462(12) 0.1168(3) 0.32913(8) 0.0125(3) Uani 1 1 d . . . . .
C8 C -0.12355(13) -0.1722(3) 0.25497(10) 0.0231(4) Uani 1 1 d . . . . .
C9 C -0.1442(2) -0.3646(4) 0.28921(14) 0.0427(6) Uani 1 1 d . . . . .
C10 C -0.10074(11) -0.3001(3) 0.08710(7) 0.0119(3) Uani 1 1 d . . . . .
C11 C -0.19262(12) -0.3884(3) 0.09081(8) 0.0131(3) Uani 1 1 d . . . . .
C12 C -0.27989(11) -0.3398(3) 0.05384(8) 0.0139(3) Uani 1 1 d . . . . .
C13 C -0.36278(13) -0.4412(3) 0.06956(10) 0.0226(4) Uani 1 1 d . . . . .
Na1 Na -0.06262(4) 0.22435(10) 0.08671(3) 0.01324(15) Uani 1 1 d . . . . .
Na2 Na 0.05706(4) 0.50967(10) 0.21836(3) 0.01389(15) Uani 1 1 d . . . . .
Na3 Na 0.10371(5) -0.17893(10) 0.11541(3) 0.01588(15) Uani 1 1 d . . . . .
O1 O 0.27437(8) 0.89282(18) 0.43037(5) 0.0138(2) Uani 1 1 d . . . . .
O2 O 0.09925(8) 0.32173(18) 0.32458(5) 0.0148(2) Uani 1 1 d . . . . .
O3 O -0.02843(8) -0.18771(18) 0.25046(6) 0.0160(3) Uani 1 1 d . . . . .
O4 O 0.11475(8) -0.0701(2) 0.22579(6) 0.0185(3) Uani 1 1 d . . . . .
O5 O -0.02745(8) 0.17781(18) 0.20079(5) 0.0149(2) Uani 1 1 d . . . . .
O6 O 0.19622(9) 0.5207(2) 0.18543(7) 0.0175(3) Uani 1 1 d . . . . .
O7 O -0.02869(8) 0.58523(18) 0.10917(6) 0.0145(2) Uani 1 1 d . . . . .
O8 O -0.16199(9) 0.2508(2) -0.02176(6) 0.0144(2) Uani 1 1 d . . . . .
O9 O 0.07379(9) 0.1485(2) 0.06165(7) 0.0163(3) Uani 1 1 d . . . . .
O10 O -0.09800(8) -0.12105(18) 0.06469(6) 0.0155(2) Uani 1 1 d . . . . .
P1 P 0.03177(3) 0.01482(7) 0.24386(2) 0.01163(10) Uani 1 1 d . . . . .
H11A H -0.1865(13) -0.496(3) 0.1260(9) 0.014(5) Uiso 1 1 d . . . . .
H7A H 0.0090(14) 0.122(3) 0.3443(9) 0.018(5) Uiso 1 1 d . . . . .
H7B H 0.1125(14) 0.035(3) 0.3598(10) 0.020(5) Uiso 1 1 d . . . . .
H8B H -0.1283(14) -0.044(3) 0.2782(10) 0.019(5) Uiso 1 1 d . . . . .
H8A H -0.1663(15) -0.156(3) 0.2103(11) 0.026(5) Uiso 1 1 d . . . . .
H13C H -0.3438(14) -0.541(4) 0.1053(10) 0.025(5) Uiso 1 1 d . . . . .
H8E H -0.1864(16) 0.371(4) -0.0319(11) 0.034(6) Uiso 1 1 d . . . . .
H9E H 0.1150(17) 0.239(4) 0.0699(12) 0.034(7) Uiso 1 1 d . . . . .
H8D H -0.1974(18) 0.177(4) -0.0198(12) 0.039(8) Uiso 1 1 d . . . . .
H13A H -0.4005(16) -0.334(4) 0.0837(11) 0.032(6) Uiso 1 1 d . . . . .
H13B H -0.4032(17) -0.517(4) 0.0310(12) 0.039(7) Uiso 1 1 d . . . . .
H6B H 0.2079(17) 0.470(4) 0.1523(13) 0.042(7) Uiso 1 1 d . . . . .
H9B H -0.2082(19) -0.363(4) 0.2956(13) 0.049(7) Uiso 1 1 d . . . . .
H9D H 0.0688(18) 0.127(4) 0.0213(14) 0.045(8) Uiso 1 1 d . . . . .
H9C H -0.1381(18) -0.491(4) 0.2653(13) 0.046(7) Uiso 1 1 d . . . . .
H9A H -0.0979(18) -0.370(4) 0.3339(13) 0.042(7) Uiso 1 1 d . . . . .
H6A H 0.2471(18) 0.515(4) 0.2160(12) 0.035(7) Uiso 1 1 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
C1 O1 1.3141(19) . ?
C1 C6 1.406(2) . ?
C1 C2 1.427(2) . ?
C2 C3 1.387(2) . ?
C2 C12 1.493(2) 4_666 ?
C3 C4 1.393(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 O2 1.3855(18) . ?
C6 H6 0.9500 . ?
C7 O2 1.432(2) . ?
C7 P1 1.8192(16) . ?
C7 H7A 0.96(2) . ?
C7 H7B 0.96(2) . ?
C8 O3 1.441(2) . ?
C8 C9 1.506(3) . ?
C8 H8B 0.97(2) . ?
C8 H8A 0.97(2) . ?
C9 H9B 0.99(3) . ?
C9 H9C 0.97(3) . ?
C9 H9A 0.98(3) . ?
C10 O10 1.251(2) . ?
C10 O7 1.2702(19) 1_545 ?
C10 C11 1.497(2) . ?
C10 Na3 3.0144(17) . ?
C10 Na1 3.1216(18) 1_545 ?
C11 C12 1.336(2) . ?
C11 H11A 0.994(19) . ?
C12 C13 1.507(2) . ?
C13 H13C 0.96(2) . ?
C13 H13A 0.99(2) . ?
C13 H13B 0.98(2) . ?
Na1 O9 2.2781(14) . ?
Na1 O5 2.2943(12) . ?
Na1 O10 2.3058(13) . ?
Na1 O8 2.3148(13) . ?
Na1 O7 2.4004(13) . ?
Na1 Na2 3.3490(9) . ?
Na1 P1 3.4361(7) . ?
Na1 Na3 3.5136(9) . ?
Na1 Na3 4.0747(9) 3 ?
Na1 H8D 2.53(3) . ?
Na2 O7 2.3092(12) . ?
Na2 O6 2.3501(14) . ?
Na2 O2 2.4361(13) . ?
Na2 O5 2.4543(13) . ?
Na2 O3 2.5193(13) 1_565 ?
Na2 O4 2.8348(15) 1_565 ?
Na2 Na3 3.1524(9) 1_565 ?
Na2 P1 3.2771(8) . ?
Na2 P1 3.3419(8) 1_565 ?
Na3 O4 2.3578(13) . ?
Na3 O9 2.3717(14) . ?
Na3 O8 2.3887(14) 3 ?
Na3 O7 2.4550(13) 1_545 ?
Na3 O6 2.5694(15) 1_545 ?
Na3 O10 2.8893(13) . ?
Na3 P1 3.3833(8) . ?
O3 P1 1.6099(12) . ?
O4 P1 1.4880(12) . ?
O5 P1 1.4912(12) . ?
O6 H6B 0.83(3) . ?
O6 H6A 0.83(3) . ?
O8 H8E 0.85(3) . ?
O8 H8D 0.72(3) . ?
O9 H9E 0.83(3) . ?
O9 H9D 0.83(3) . ?

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 C1 C6 119.25(14) . . ?
O1 C1 C2 122.96(14) . . ?
C6 C1 C2 117.79(14) . . ?
C3 C2 C1 118.62(15) . . ?
C3 C2 C12 120.11(14) . 4_666 ?
C1 C2 C12 121.01(15) . 4_666 ?
C2 C3 C4 123.10(15) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C5 C4 C3 117.82(15) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C6 C5 O2 114.70(14) . . ?
C6 C5 C4 120.90(15) . . ?
O2 C5 C4 124.39(15) . . ?
C5 C6 C1 121.73(14) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
O2 C7 P1 105.69(10) . . ?
O2 C7 H7A 110.1(12) . . ?
P1 C7 H7A 108.5(11) . . ?
O2 C7 H7B 110.0(12) . . ?
P1 C7 H7B 112.6(12) . . ?
H7A C7 H7B 109.9(16) . . ?
O3 C8 C9 107.93(18) . . ?
O3 C8 H8B 107.6(12) . . ?
C9 C8 H8B 114.6(12) . . ?
O3 C8 H8A 109.1(12) . . ?
C9 C8 H8A 112.1(13) . . ?
H8B C8 H8A 105.4(18) . . ?
C8 C9 H9B 112.6(16) . . ?
C8 C9 H9C 113.0(15) . . ?
H9B C9 H9C 108(2) . . ?
C8 C9 H9A 107.2(15) . . ?
H9B C9 H9A 108(2) . . ?
H9C C9 H9A 108(2) . . ?
O10 C10 O7 123.98(15) . 1_545 ?
O10 C10 C11 119.89(14) . . ?
O7 C10 C11 116.11(14) 1_545 . ?
O10 C10 Na3 72.22(9) . . ?
O7 C10 Na3 52.39(8) 1_545 . ?
C11 C10 Na3 164.68(11) . . ?
O10 C10 Na1 151.93(11) . 1_545 ?
O7 C10 Na1 45.12(8) 1_545 1_545 ?
C11 C10 Na1 78.06(9) . 1_545 ?
Na3 C10 Na1 94.80(5) . 1_545 ?
C12 C11 C10 128.53(15) . . ?
C12 C11 H11A 117.1(11) . . ?
C10 C11 H11A 114.4(11) . . ?
C11 C12 C2 126.80(15) . 4_565 ?
C11 C12 C13 119.06(15) . . ?
C2 C12 C13 114.13(14) 4_565 . ?
C12 C13 H13C 112.5(12) . . ?
C12 C13 H13A 108.9(13) . . ?
H13C C13 H13A 107.9(18) . . ?
C12 C13 H13B 112.5(13) . . ?
H13C C13 H13B 105.7(19) . . ?
H13A C13 H13B 109.2(19) . . ?
O9 Na1 O5 104.78(5) . . ?
O9 Na1 O10 84.97(5) . . ?
O5 Na1 O10 92.82(5) . . ?
O9 Na1 O8 98.62(5) . . ?
O5 Na1 O8 154.99(5) . . ?
O10 Na1 O8 80.44(5) . . ?
O9 Na1 O7 95.94(5) . . ?
O5 Na1 O7 87.35(4) . . ?
O10 Na1 O7 178.99(5) . . ?
O8 Na1 O7 99.00(5) . . ?
O9 Na1 C10 112.62(5) . 1_565 ?
O5 Na1 C10 96.52(4) . 1_565 ?
O10 Na1 C10 157.01(5) . 1_565 ?
O8 Na1 C10 82.27(5) . 1_565 ?
O7 Na1 C10 22.02(4) . 1_565 ?
O9 Na1 Na2 90.55(4) . . ?
O5 Na1 Na2 47.12(3) . . ?
O10 Na1 Na2 136.90(4) . . ?
O8 Na1 Na2 142.41(4) . . ?
O7 Na1 Na2 43.59(3) . . ?
C10 Na1 Na2 60.69(3) 1_565 . ?
O9 Na1 P1 89.29(4) . . ?
O5 Na1 P1 19.67(3) . . ?
O10 Na1 P1 79.32(3) . . ?
O8 Na1 P1 157.50(4) . . ?
O7 Na1 P1 101.09(3) . . ?
C10 Na1 P1 114.14(3) 1_565 . ?
Na2 Na1 P1 57.743(16) . . ?
O9 Na1 Na3 41.93(3) . . ?
O5 Na1 Na3 77.77(4) . . ?
O10 Na1 Na3 54.91(3) . . ?
O8 Na1 Na3 115.94(4) . . ?
O7 Na1 Na3 126.08(4) . . ?
C10 Na1 Na3 147.83(4) 1_565 . ?
Na2 Na1 Na3 95.11(2) . . ?
P1 Na1 Na3 58.253(16) . . ?
O9 Na1 Na3 68.20(4) . 3 ?
O5 Na1 Na3 167.54(4) . 3 ?
O10 Na1 Na3 76.59(3) . 3 ?
O8 Na1 Na3 30.49(3) . 3 ?
O7 Na1 Na3 103.35(3) . 3 ?
C10 Na1 Na3 95.74(3) 1_565 3 ?
Na2 Na1 Na3 140.13(2) . 3 ?
P1 Na1 Na3 148.14(2) . 3 ?
Na3 Na1 Na3 90.631(19) . 3 ?
O9 Na1 H8D 107.5(6) . . ?
O5 Na1 H8D 140.6(6) . . ?
O10 Na1 H8D 68.5(6) . . ?
O8 Na1 H8D 16.2(6) . . ?
O7 Na1 H8D 110.8(6) . . ?
C10 Na1 H8D 91.4(6) 1_565 . ?
Na2 Na1 H8D 151.3(6) . . ?
P1 Na1 H8D 141.6(6) . . ?
Na3 Na1 H8D 113.3(6) . . ?
Na3 Na1 H8D 41.1(6) 3 . ?
O7 Na2 O6 89.30(5) . . ?
O7 Na2 O2 156.84(5) . . ?
O6 Na2 O2 105.12(5) . . ?
O7 Na2 O5 85.75(4) . . ?
O6 Na2 O5 115.77(5) . . ?
O2 Na2 O5 71.74(4) . . ?
O7 Na2 O3 85.42(4) . 1_565 ?
O6 Na2 O3 127.03(5) . 1_565 ?
O2 Na2 O3 99.43(4) . 1_565 ?
O5 Na2 O3 116.30(5) . 1_565 ?
O7 Na2 O4 85.59(4) . 1_565 ?
O6 Na2 O4 73.23(4) . 1_565 ?
O2 Na2 O4 115.63(4) . 1_565 ?
O5 Na2 O4 167.42(4) . 1_565 ?
O3 Na2 O4 53.83(4) 1_565 1_565 ?
O7 Na2 Na3 50.59(3) . 1_565 ?
O6 Na2 Na3 53.28(4) . 1_565 ?
O2 Na2 Na3 151.95(4) . 1_565 ?
O5 Na2 Na3 131.11(4) . 1_565 ?
O3 Na2 Na3 84.82(3) 1_565 1_565 ?
O4 Na2 Na3 46.00(3) 1_565 1_565 ?
O7 Na2 P1 107.97(4) . . ?
O6 Na2 P1 103.12(4) . . ?
O2 Na2 P1 51.66(3) . . ?
O5 Na2 P1 25.33(3) . . ?
O3 Na2 P1 128.59(4) 1_565 . ?
O4 Na2 P1 166.08(3) 1_565 . ?
Na3 Na2 P1 142.06(2) 1_565 . ?
O7 Na2 P1 83.95(3) . 1_565 ?
O6 Na2 P1 99.44(4) . 1_565 ?
O2 Na2 P1 110.71(3) . 1_565 ?
O5 Na2 P1 143.11(4) . 1_565 ?
O3 Na2 P1 27.59(3) 1_565 1_565 ?
O4 Na2 P1 26.27(3) 1_565 1_565 ?
Na3 Na2 P1 62.716(18) 1_565 1_565 ?
P1 Na2 P1 154.47(2) . 1_565 ?
O7 Na2 Na1 45.78(3) . . ?
O6 Na2 Na1 94.64(4) . . ?
O2 Na2 Na1 113.75(4) . . ?
O5 Na2 Na1 43.24(3) . . ?
O3 Na2 Na1 117.05(4) 1_565 . ?
O4 Na2 Na1 130.61(3) 1_565 . ?
Na3 Na2 Na1 87.97(2) 1_565 . ?
P1 Na2 Na1 62.461(17) . . ?
P1 Na2 Na1 127.52(2) 1_565 . ?
O4 Na3 O9 98.25(5) . . ?
O4 Na3 O8 155.38(5) . 3 ?
O9 Na3 O8 81.49(5) . 3 ?
O4 Na3 O7 93.84(5) . 1_545 ?
O9 Na3 O7 119.33(5) . 1_545 ?
O8 Na3 O7 107.84(5) 3 1_545 ?
O4 Na3 O6 78.35(5) . 1_545 ?
O9 Na3 O6 159.35(5) . 1_545 ?
O8 Na3 O6 93.20(5) 3 1_545 ?
O7 Na3 O6 81.31(4) 1_545 1_545 ?
O4 Na3 O10 95.23(4) . . ?
O9 Na3 O10 71.33(4) . . ?
O8 Na3 O10 107.79(4) 3 . ?
O7 Na3 O10 48.39(4) 1_545 . ?
O6 Na3 O10 129.05(4) 1_545 . ?
O4 Na3 C10 92.97(5) . . ?
O9 Na3 C10 95.66(5) . . ?
O8 Na3 C10 111.60(5) 3 . ?
O7 Na3 C10 24.20(4) 1_545 . ?
O6 Na3 C10 104.82(5) 1_545 . ?
O10 Na3 C10 24.35(4) . . ?
O4 Na3 Na2 59.87(4) . 1_545 ?
O9 Na3 Na2 147.13(4) . 1_545 ?
O8 Na3 Na2 128.99(4) 3 1_545 ?
O7 Na3 Na2 46.62(3) 1_545 1_545 ?
O6 Na3 Na2 47.15(3) 1_545 1_545 ?
O10 Na3 Na2 85.69(3) . 1_545 ?
C10 Na3 Na2 64.11(3) . 1_545 ?
O4 Na3 P1 22.01(3) . . ?
O9 Na3 P1 89.04(4) . . ?
O8 Na3 P1 169.37(4) 3 . ?
O7 Na3 P1 80.99(3) 1_545 . ?
O6 Na3 P1 94.02(3) 1_545 . ?
O10 Na3 P1 73.33(3) . . ?
C10 Na3 P1 73.97(3) . . ?
Na2 Na3 P1 61.383(18) 1_545 . ?
O4 Na3 Na1 78.07(4) . . ?
O9 Na3 Na1 39.93(3) . . ?
O8 Na3 Na1 113.90(4) 3 . ?
O7 Na3 Na1 86.63(3) 1_545 . ?
O6 Na3 Na1 152.65(4) 1_545 . ?
O10 Na3 Na1 40.77(3) . . ?
C10 Na3 Na1 62.90(4) . . ?
Na2 Na3 Na1 107.94(2) 1_545 . ?
P1 Na3 Na1 59.726(16) . . ?
O4 Na3 Na1 166.15(4) . 3 ?
O9 Na3 Na1 68.09(4) . 3 ?
O8 Na3 Na1 29.45(3) 3 3 ?
O7 Na3 Na1 91.19(3) 1_545 3 ?
O6 Na3 Na1 115.21(4) 1_545 3 ?
O10 Na3 Na1 78.56(3) . 3 ?
C10 Na3 Na1 86.37(3) . 3 ?
Na2 Na3 Na1 130.98(2) 1_545 3 ?
P1 Na3 Na1 148.34(2) . 3 ?
Na1 Na3 Na1 89.370(19) . 3 ?
C5 O2 C7 117.44(12) . . ?
C5 O2 Na2 117.86(10) . . ?
C7 O2 Na2 121.11(9) . . ?
C8 O3 P1 121.59(11) . . ?
C8 O3 Na2 130.21(10) . 1_545 ?
P1 O3 Na2 105.95(6) . 1_545 ?
P1 O4 Na3 121.57(7) . . ?
P1 O4 Na2 96.25(6) . 1_545 ?
Na3 O4 Na2 74.12(4) . 1_545 ?
P1 O5 Na1 129.14(7) . . ?
P1 O5 Na2 109.91(6) . . ?
Na1 O5 Na2 89.64(4) . . ?
Na2 O6 Na3 79.57(4) . 1_565 ?
Na2 O6 H6B 130.0(17) . . ?
Na3 O6 H6B 92.0(18) 1_565 . ?
Na2 O6 H6A 116.9(16) . . ?
Na3 O6 H6A 133.1(17) 1_565 . ?
H6B O6 H6A 105(2) . . ?
C10 O7 Na2 130.12(10) 1_565 . ?
C10 O7 Na1 112.86(10) 1_565 . ?
Na2 O7 Na1 90.63(5) . . ?
C10 O7 Na3 103.41(10) 1_565 1_565 ?
Na2 O7 Na3 82.80(4) . 1_565 ?
Na1 O7 Na3 136.99(5) . 1_565 ?
Na1 O8 Na3 120.06(6) . 3 ?
Na1 O8 H8E 114.3(15) . . ?
Na3 O8 H8E 101.5(15) 3 . ?
Na1 O8 H8D 99(2) . . ?
Na3 O8 H8D 111(2) 3 . ?
H8E O8 H8D 111(3) . . ?
Na1 O9 Na3 98.14(5) . . ?
Na1 O9 H9E 116.7(16) . . ?
Na3 O9 H9E 120.4(17) . . ?
Na1 O9 H9D 116.0(18) . . ?
Na3 O9 H9D 106.1(19) . . ?
H9E O9 H9D 100(2) . . ?
C10 O10 Na1 148.16(10) . . ?
C10 O10 Na3 83.43(9) . . ?
Na1 O10 Na3 84.32(4) . . ?
O4 P1 O5 119.59(7) . . ?
O4 P1 O3 103.85(7) . . ?
O5 P1 O3 112.34(7) . . ?
O4 P1 C7 111.71(7) . . ?
O5 P1 C7 105.96(7) . . ?
O3 P1 C7 102.13(7) . . ?

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 C1 C2 C3 -179.63(15) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
O1 C1 C2 C12 6.1(2) . . . 4_666 ?
C6 C1 C2 C12 -174.41(14) . . . 4_666 ?
C1 C2 C3 C4 1.7(3) . . . . ?
C12 C2 C3 C4 176.08(16) 4_666 . . . ?
C2 C3 C4 C5 -2.4(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C3 C4 C5 O2 -177.48(15) . . . . ?
O2 C5 C6 C1 179.13(14) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
O1 C1 C6 C5 178.73(15) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
O10 C10 C11 C12 25.5(3) . . . . ?
O7 C10 C11 C12 -156.12(17) 1_545 . . . ?
Na3 C10 C11 C12 165.4(3) . . . . ?
Na1 C10 C11 C12 -131.20(18) 1_545 . . . ?
C10 C11 C12 C2 5.4(3) . . . 4_565 ?
C10 C11 C12 C13 -176.32(16) . . . . ?
C6 C5 O2 C7 162.49(14) . . . . ?
C4 C5 O2 C7 -18.6(2) . . . . ?
C6 C5 O2 Na2 -38.63(17) . . . . ?
C4 C5 O2 Na2 140.28(14) . . . . ?
P1 C7 O2 C5 179.44(11) . . . . ?
P1 C7 O2 Na2 21.29(14) . . . . ?
C9 C8 O3 P1 -156.17(14) . . . . ?
C9 C8 O3 Na2 43.4(2) . . . 1_545 ?
O7 C10 O10 Na1 -76.5(3) 1_545 . . . ?
C11 C10 O10 Na1 101.7(2) . . . . ?
Na3 C10 O10 Na1 -68.02(19) . . . . ?
Na1 C10 O10 Na1 -133.53(18) 1_545 . . . ?
O7 C10 O10 Na3 -8.50(15) 1_545 . . . ?
C11 C10 O10 Na3 169.70(13) . . . . ?
Na1 C10 O10 Na3 -65.5(2) 1_545 . . . ?
Na3 O4 P1 O5 -48.00(11) . . . . ?
Na2 O4 P1 O5 -123.18(6) 1_545 . . . ?
Na3 O4 P1 O3 78.17(9) . . . . ?
Na2 O4 P1 O3 2.99(6) 1_545 . . . ?
Na3 O4 P1 C7 -172.50(8) . . . . ?
Na2 O4 P1 C7 112.32(7) 1_545 . . . ?
Na1 O5 P1 O4 33.04(12) . . . . ?
Na2 O5 P1 O4 -73.58(9) . . . . ?
Na1 O5 P1 O3 -89.02(9) . . . . ?
Na2 O5 P1 O3 164.36(6) . . . . ?
Na1 O5 P1 C7 160.26(9) . . . . ?
Na2 O5 P1 C7 53.64(8) . . . . ?
C8 O3 P1 O4 -168.06(12) . . . . ?
Na2 O3 P1 O4 -3.48(7) 1_545 . . . ?
C8 O3 P1 O5 -37.43(14) . . . . ?
Na2 O3 P1 O5 127.15(6) 1_545 . . . ?
C8 O3 P1 C7 75.67(14) . . . . ?
Na2 O3 P1 C7 -119.75(7) 1_545 . . . ?
O2 C7 P1 O4 82.73(12) . . . . ?
O2 C7 P1 O5 -49.08(12) . . . . ?
O2 C7 P1 O3 -166.84(10) . . . . ?

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
_geom_hbond_publ_flag
O8 H8E O1 0.85(3) 1.74(3) 2.5749(17) 166(2) 4_575 yes
O9 H9E O1 0.83(3) 1.92(3) 2.7110(17) 161(2) 2_545 yes
O6 H6B O1 0.83(3) 1.88(3) 2.6938(17) 171(3) 2_545 yes
O9 H9D O10 0.83(3) 1.96(3) 2.7539(17) 161(3) 3 yes
O6 H6A O4 0.83(3) 2.12(3) 2.9322(17) 163(2) 2 yes

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 892005'
loop_
_audit_author_name
_audit_author_address
'Majid Motevalli'
;Queen Mary University of London
United Kingdom
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 O6 P'
_chemical_formula_weight         298.22

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0955(3)
_cell_length_b                   24.2238(10)
_cell_length_c                   8.2176(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.643(2)
_cell_angle_gamma                90
_cell_volume                     1353.27(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9352
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker-Nonius FR591 rotating anode'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_reflns_number            10427
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.996
_diffrn_reflns_theta_max         26.727
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2846
_reflns_number_gt                2029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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     
'w=1/[σ²(Fo²)+(0.0696P)²+4.7216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2846
_refine_ls_number_parameters     206
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1864
_refine_ls_wR_factor_gt          0.1576
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.943
_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_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
C1 C -0.3564(6) 0.51251(15) 0.2531(5) 0.0284(8) Uani 1 1 d . . . . .
C2 C -0.5642(6) 0.50122(15) 0.2016(5) 0.0286(8) Uani 1 1 d . . . . .
H2 H -0.6472 0.5233 0.1146 0.034 Uiso 1 1 calc R U . . .
C3 C -0.6467(5) 0.46091(16) 0.2706(5) 0.0274(8) Uani 1 1 d . . . . .
C4 C -0.5208(6) 0.42727(15) 0.4035(5) 0.0274(8) Uani 1 1 d . . . . .
C5 C -0.3201(6) 0.43773(15) 0.4521(4) 0.0255(8) Uani 1 1 d . . . . .
C6 C -0.8637(6) 0.45015(18) 0.2143(6) 0.0376(10) Uani 1 1 d . . . . .
H6A H -0.9268 0.4751 0.1207 0.056 Uiso 1 1 calc R U . . .
H6B H -0.9184 0.4565 0.3095 0.056 Uiso 1 1 calc R U . . .
H6C H -0.8878 0.4118 0.1758 0.056 Uiso 1 1 calc R U . . .
C7 C -0.5868(6) 0.38360(16) 0.4857(5) 0.0307(9) Uani 1 1 d . . . . .
H7 H -0.7234 0.3755 0.4565 0.037 Uiso 1 1 calc R U . . .
C8 C -0.4581(6) 0.35252(16) 0.6071(5) 0.0326(9) Uani 1 1 d . . . . .
H8 H -0.5057 0.3234 0.6621 0.039 Uiso 1 1 calc R U . . .
C9 C -0.2560(6) 0.36372(15) 0.6502(5) 0.0284(8) Uani 1 1 d . . . . .
C10 C -0.1849(6) 0.40691(15) 0.5748(5) 0.0270(8) Uani 1 1 d . . . . .
H10 H -0.0485 0.4153 0.6058 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0683(6) 0.33473(16) 0.8047(5) 0.0296(9) Uani 1 1 d . . . . .
H11A H 0.1101 0.3730 0.8392 0.036 Uiso 1 1 calc R U . . .
H11B H 0.1072 0.3258 0.7013 0.036 Uiso 1 1 calc R U . . .
C12A C 0.5749(14) 0.3025(5) 1.1183(12) 0.051(3) Uani 0.685(19) 1 d . U P A 1
H12A H 0.5340 0.3024 1.2238 0.062 Uiso 0.685(19) 1 calc R U P A 1
H12B H 0.6756 0.2734 1.1286 0.062 Uiso 0.685(19) 1 calc R U P A 1
C13A C 0.6610(11) 0.3568(3) 1.0984(9) 0.045(2) Uani 0.678(15) 1 d . U P A 1
H13A H 0.7740 0.3641 1.1973 0.055 Uiso 0.678(15) 1 calc R U P A 1
H13B H 0.5619 0.3857 1.0894 0.055 Uiso 0.678(15) 1 calc R U P A 1
H13C H 0.7043 0.3567 0.9953 0.055 Uiso 0.678(15) 1 calc R U P A 1
C12B C 0.518(3) 0.3342(8) 1.063(3) 0.050(6) Uani 0.315(19) 1 d . U P A 2
H12C H 0.5712 0.3572 0.9866 0.060 Uiso 0.315(19) 1 calc R U P A 2
H12D H 0.4385 0.3580 1.1159 0.060 Uiso 0.315(19) 1 calc R U P A 2
C13B C 0.671(4) 0.3088(10) 1.188(3) 0.076(8) Uani 0.322(15) 1 d . U P A 2
H13D H 0.7566 0.3372 1.2557 0.091 Uiso 0.322(15) 1 calc R U P A 2
H13E H 0.7476 0.2854 1.1328 0.091 Uiso 0.322(15) 1 calc R U P A 2
H13F H 0.6155 0.2861 1.2612 0.091 Uiso 0.322(15) 1 calc R U P A 2
O1 O -0.2403(4) 0.48007(10) 0.3810(3) 0.0270(6) Uani 1 1 d . . . . .
O2 O -0.2710(4) 0.54746(11) 0.1956(4) 0.0365(7) Uani 1 1 d . . . . .
O3 O -0.1406(4) 0.32965(11) 0.7713(4) 0.0348(7) Uani 1 1 d . . . . .
O4 O 0.1076(4) 0.22854(11) 0.9145(4) 0.0332(7) Uani 1 1 d . . . . .
O5 O 0.1484(5) 0.30311(12) 1.1357(4) 0.0438(8) Uani 1 1 d . . . . .
O6 O 0.4016(4) 0.28994(12) 0.9708(4) 0.0401(7) Uani 1 1 d . . . . .
P1 P 0.18239(17) 0.28757(4) 0.97235(13) 0.0311(3) Uani 1 1 d . . . . .
H4 H 0.129(8) 0.220(2) 0.808(8) 0.075(18) Uiso 1 1 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
C1 O2 1.213(5) . ?
C1 O1 1.380(4) . ?
C1 C2 1.439(5) . ?
C2 C3 1.345(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.447(5) . ?
C3 C6 1.498(5) . ?
C4 C5 1.388(5) . ?
C4 C7 1.406(5) . ?
C5 O1 1.380(4) . ?
C5 C10 1.393(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.369(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(6) . ?
C8 H8 0.9500 . ?
C9 O3 1.370(5) . ?
C9 C10 1.382(5) . ?
C10 H10 0.9500 . ?
C11 O3 1.433(5) . ?
C11 P1 1.794(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12A C13A 1.480(13) . ?
C12A O6 1.489(10) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C12B C13B 1.40(3) . ?
C12B O6 1.431(16) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
O4 P1 1.552(3) . ?
O4 H4 0.95(6) . ?
O5 P1 1.479(3) . ?
O6 P1 1.560(3) . ?

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
O2 C1 O1 116.0(3) . . ?
O2 C1 C2 127.0(4) . . ?
O1 C1 C2 117.0(3) . . ?
C3 C2 C1 123.2(4) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 C6 121.9(4) . . ?
C4 C3 C6 119.5(3) . . ?
C5 C4 C7 117.0(4) . . ?
C5 C4 C3 118.4(3) . . ?
C7 C4 C3 124.6(4) . . ?
O1 C5 C4 121.7(3) . . ?
O1 C5 C10 115.1(3) . . ?
C4 C5 C10 123.2(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 121.3(4) . . ?
C8 C7 H7 119.3 . . ?
C4 C7 H7 119.3 . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O3 C9 C10 124.2(3) . . ?
O3 C9 C8 115.0(3) . . ?
C10 C9 C8 120.8(4) . . ?
C9 C10 C5 117.8(4) . . ?
C9 C10 H10 121.1 . . ?
C5 C10 H10 121.1 . . ?
O3 C11 P1 107.9(2) . . ?
O3 C11 H11A 110.1 . . ?
P1 C11 H11A 110.1 . . ?
O3 C11 H11B 110.1 . . ?
P1 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C13A C12A O6 111.2(8) . . ?
C13A C12A H12A 109.4 . . ?
O6 C12A H12A 109.4 . . ?
C13A C12A H12B 109.4 . . ?
O6 C12A H12B 109.4 . . ?
H12A C12A H12B 108.0 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C13B C12B O6 105.4(18) . . ?
C13B C12B H12C 110.7 . . ?
O6 C12B H12C 110.7 . . ?
C13B C12B H12D 110.7 . . ?
O6 C12B H12D 110.7 . . ?
H12C C12B H12D 108.8 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C5 O1 C1 121.2(3) . . ?
C9 O3 C11 117.2(3) . . ?
P1 O4 H4 110(3) . . ?
C12B O6 P1 116.7(8) . . ?
C12A O6 P1 126.4(4) . . ?
O5 P1 O4 112.49(17) . . ?
O5 P1 O6 114.82(19) . . ?
O4 P1 O6 106.62(16) . . ?
O5 P1 C11 112.31(18) . . ?
O4 P1 C11 108.17(18) . . ?
O6 P1 C11 101.67(17) . . ?

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
O2 C1 C2 C3 178.9(4) . . . . ?
O1 C1 C2 C3 -0.7(5) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C1 C2 C3 C6 180.0(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C6 C3 C4 C5 179.4(3) . . . . ?
C2 C3 C4 C7 -179.5(3) . . . . ?
C6 C3 C4 C7 0.6(6) . . . . ?
C7 C4 C5 O1 -179.1(3) . . . . ?
C3 C4 C5 O1 2.0(5) . . . . ?
C7 C4 C5 C10 0.8(5) . . . . ?
C3 C4 C5 C10 -178.1(3) . . . . ?
C5 C4 C7 C8 -0.6(5) . . . . ?
C3 C4 C7 C8 178.1(4) . . . . ?
C4 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 O3 -179.1(3) . . . . ?
C7 C8 C9 C10 1.8(6) . . . . ?
O3 C9 C10 C5 179.4(3) . . . . ?
C8 C9 C10 C5 -1.7(5) . . . . ?
O1 C5 C10 C9 -179.7(3) . . . . ?
C4 C5 C10 C9 0.4(5) . . . . ?
C4 C5 O1 C1 -2.6(5) . . . . ?
C10 C5 O1 C1 177.4(3) . . . . ?
O2 C1 O1 C5 -177.7(3) . . . . ?
C2 C1 O1 C5 1.9(5) . . . . ?
C10 C9 O3 C11 -8.6(5) . . . . ?
C8 C9 O3 C11 172.4(3) . . . . ?
P1 C11 O3 C9 177.9(3) . . . . ?
C13B C12B O6 C12A 3.5(14) . . . . ?
C13B C12B O6 P1 119.4(14) . . . . ?
C13A C12A O6 C12B -23.5(13) . . . . ?
C13A C12A O6 P1 -110.5(6) . . . . ?
C12B O6 P1 O5 -37.9(11) . . . . ?
C12A O6 P1 O5 4.3(6) . . . . ?
C12B O6 P1 O4 -163.2(11) . . . . ?
C12A O6 P1 O4 -121.0(6) . . . . ?
C12B O6 P1 C11 83.6(11) . . . . ?
C12A O6 P1 C11 125.8(6) . . . . ?
O3 C11 P1 O5 -66.6(3) . . . . ?
O3 C11 P1 O4 58.1(3) . . . . ?
O3 C11 P1 O6 170.1(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
O4 H4 O5 0.95(6) 1.57(6) 2.510(4) 171(6) 4_565

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

