# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1016772'
_audit_update_record             
;
2014-07-29 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H52 N5 O10 P3'
_chemical_formula_sum            'C26 H52 N5 O10 P3'
_chemical_formula_weight         687.63

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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

_cell_length_a                   12.4915(2)
_cell_length_b                   13.3518(2)
_cell_length_c                   9.97050(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1662.92(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    106(8)
_cell_measurement_reflns_used    14536
_cell_measurement_theta_min      3.0160
_cell_measurement_theta_max      38.4190

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_ambient_temperature      106(8)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            27358
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         38.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8948
_reflns_number_gt                8348
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    1.000
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2006)'
_computing_publication_material  'PLATON (Spek, 2006)'

_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)+(0.0378P)²+0.1740P] 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 3501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.460(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8948
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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
P1 P 0.0000 0.0000 0.03945(4) 0.01192(6) Uani 1 2 d S T P . .
P2 P 0.09017(2) 0.06222(2) 0.28243(3) 0.01220(5) Uani 1 1 d . . . . .
O5 O -0.05703(7) 0.07035(6) -0.06672(8) 0.01665(14) Uani 1 1 d . . . . .
O4 O 0.08323(7) 0.20866(6) -0.21874(9) 0.01845(14) Uani 1 1 d . . . . .
O3 O 0.28824(8) 0.06182(7) -0.24055(9) 0.02203(16) Uani 1 1 d . . . . .
O1 O 0.20620(6) 0.02583(6) 0.32703(8) 0.01605(13) Uani 1 1 d . . . . .
O2 O 0.35746(7) 0.05428(7) 0.10830(9) 0.01976(15) Uani 1 1 d . . . . .
N1 N 0.08540(7) 0.06191(7) 0.12211(8) 0.01446(13) Uani 1 1 d . . . . .
N2 N 0.0000 0.0000 0.35833(12) 0.01455(19) Uani 1 2 d S T P . .
N3 N 0.09395(8) 0.17733(6) 0.34436(9) 0.01449(14) Uani 1 1 d . . . . .
C5 C 0.17271(9) 0.24457(8) 0.27962(13) 0.01853(18) Uani 1 1 d . . . . .
H5A H 0.1453 0.2667 0.1935 0.022 Uiso 1 1 calc R U . . .
H5B H 0.2390 0.2086 0.2642 0.022 Uiso 1 1 calc R U . . .
C13 C -0.06149(9) 0.17776(8) -0.05995(11) 0.01755(17) Uani 1 1 d . . . . .
H13A H -0.0141 0.2017 0.0102 0.021 Uiso 1 1 calc R U . . .
H13B H -0.1338 0.1990 -0.0386 0.021 Uiso 1 1 calc R U . . .
C12 C -0.02800(9) 0.22126(8) -0.19286(12) 0.01796(18) Uani 1 1 d . . . . .
H12A H -0.0686 0.1893 -0.2638 0.022 Uiso 1 1 calc R U . . .
H12B H -0.0450 0.2921 -0.1941 0.022 Uiso 1 1 calc R U . . .
C11 C 0.10748(9) 0.12271(8) -0.29964(12) 0.01785(17) Uani 1 1 d . . . . .
H11A H 0.0669 0.1255 -0.3825 0.021 Uiso 1 1 calc R U . . .
H11B H 0.0875 0.0621 -0.2522 0.021 Uiso 1 1 calc R U . . .
C10 C 0.22645(10) 0.12089(9) -0.33074(12) 0.02053(19) Uani 1 1 d . . . . .
H10A H 0.2364 0.0953 -0.4209 0.025 Uiso 1 1 calc R U . . .
H10B H 0.2534 0.1890 -0.3290 0.025 Uiso 1 1 calc R U . . .
C6 C 0.25792(9) -0.05616(8) 0.25998(12) 0.01772(17) Uani 1 1 d . . . . .
H6A H 0.2140 -0.0791 0.1859 0.021 Uiso 1 1 calc R U . . .
H6B H 0.2676 -0.1115 0.3218 0.021 Uiso 1 1 calc R U . . .
C7 C 0.36549(9) -0.02116(9) 0.20837(13) 0.02038(19) Uani 1 1 d . . . . .
H7A H 0.4071 0.0046 0.2829 0.024 Uiso 1 1 calc R U . . .
H7B H 0.4037 -0.0781 0.1715 0.024 Uiso 1 1 calc R U . . .
C8 C 0.33381(10) 0.01514(9) -0.02118(12) 0.01998(19) Uani 1 1 d . . . . .
H8A H 0.2777 -0.0349 -0.0149 0.024 Uiso 1 1 calc R U . . .
H8B H 0.3970 -0.0161 -0.0592 0.024 Uiso 1 1 calc R U . . .
C9 C 0.29759(10) 0.10098(9) -0.10884(12) 0.01992(19) Uani 1 1 d . . . . .
H9A H 0.2292 0.1267 -0.0782 0.024 Uiso 1 1 calc R U . . .
H9B H 0.3496 0.1549 -0.1066 0.024 Uiso 1 1 calc R U . . .
C4 C 0.19412(10) 0.33518(9) 0.36870(14) 0.0212(2) Uani 1 1 d . . . . .
H4A H 0.2274 0.3134 0.4516 0.025 Uiso 1 1 calc R U . . .
H4B H 0.2432 0.3803 0.3236 0.025 Uiso 1 1 calc R U . . .
C3 C 0.09032(11) 0.39032(8) 0.40017(13) 0.02084(19) Uani 1 1 d . . . . .
H3A H 0.0615 0.4192 0.3185 0.025 Uiso 1 1 calc R U . . .
H3B H 0.1046 0.4444 0.4625 0.025 Uiso 1 1 calc R U . . .
C2 C 0.00836(10) 0.31850(8) 0.46132(12) 0.01910(18) Uani 1 1 d . . . . .
H2A H 0.0333 0.2964 0.5486 0.023 Uiso 1 1 calc R U . . .
H2B H -0.0591 0.3532 0.4737 0.023 Uiso 1 1 calc R U . . .
C1 C -0.00871(9) 0.22754(8) 0.37073(11) 0.01732(17) Uani 1 1 d . . . . .
H1A H -0.0575 0.1810 0.4137 0.021 Uiso 1 1 calc R U . . .
H1B H -0.0405 0.2488 0.2866 0.021 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 N1 1.5813(9) . ?
P1 N1 1.5813(9) 2 ?
P1 O5 1.5844(8) 2 ?
P1 O5 1.5844(8) . ?
P2 N2 1.5911(6) . ?
P2 O1 1.5920(8) . ?
P2 N1 1.5996(9) . ?
P2 N3 1.6569(9) . ?
O5 C13 1.4368(14) . ?
O4 C12 1.4233(14) . ?
O4 C11 1.4351(14) . ?
O3 C9 1.4183(14) . ?
O3 C10 1.4236(15) . ?
O1 C6 1.4362(14) . ?
O2 C7 1.4213(15) . ?
O2 C8 1.4238(15) . ?
N2 P2 1.5911(6) 2 ?
N3 C1 1.4707(15) . ?
N3 C5 1.4801(14) . ?
C5 C4 1.5244(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C13 C12 1.5061(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C10 1.5182(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C6 C7 1.5129(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.5107(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 C3 1.5237(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C2 1.5295(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 C1 1.5284(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
N1 P1 N1 117.18(7) . 2 ?
N1 P1 O5 110.78(5) . 2 ?
N1 P1 O5 109.98(4) 2 2 ?
N1 P1 O5 109.98(4) . . ?
N1 P1 O5 110.78(5) 2 . ?
O5 P1 O5 96.15(6) 2 . ?
N2 P2 O1 110.63(4) . . ?
N2 P2 N1 116.58(5) . . ?
O1 P2 N1 108.20(5) . . ?
N2 P2 N3 109.10(4) . . ?
O1 P2 N3 98.81(5) . . ?
N1 P2 N3 112.08(5) . . ?
C13 O5 P1 125.29(7) . . ?
C12 O4 C11 113.73(9) . . ?
C9 O3 C10 115.17(9) . . ?
C6 O1 P2 120.80(7) . . ?
C7 O2 C8 113.02(9) . . ?
P1 N1 P2 123.19(6) . . ?
P2 N2 P2 123.20(8) . 2 ?
C1 N3 C5 112.40(8) . . ?
C1 N3 P2 117.69(7) . . ?
C5 N3 P2 114.78(7) . . ?
N3 C5 C4 110.12(9) . . ?
N3 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N3 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
O5 C13 C12 109.44(9) . . ?
O5 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
O5 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
O4 C12 C13 112.64(9) . . ?
O4 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
O4 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O4 C11 C10 109.52(9) . . ?
O4 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
O4 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O3 C10 C11 114.25(10) . . ?
O3 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
O3 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
O1 C6 C7 108.81(9) . . ?
O1 C6 H6A 109.9 . . ?
C7 C6 H6A 109.9 . . ?
O1 C6 H6B 109.9 . . ?
C7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O2 C7 C6 113.26(9) . . ?
O2 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O2 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O2 C8 C9 107.95(9) . . ?
O2 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
O3 C9 C8 106.30(9) . . ?
O3 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
O3 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C3 C4 C5 110.74(10) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C3 C2 110.41(9) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C1 C2 C3 110.85(10) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N3 C1 C2 110.26(9) . . ?
N3 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N3 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4



