# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1553747'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O7 P2, C6 H18 N2, 2(H2 O)'
_chemical_formula_sum            'C10 H33 N3 O9 P2'
_chemical_formula_weight         401.33

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.1160(4)
_cell_length_b                   13.6637(7)
_cell_length_c                   19.0629(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1853.50(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1813
_cell_measurement_theta_min      2.1322
_cell_measurement_theta_max      25.6215

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.282
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.93602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            6656
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3503
_reflns_number_gt                3095
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     1.000
_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 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.0966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.44(13)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3503
_refine_ls_number_parameters     275
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.054
_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 0.87820(13) 0.68168(6) 0.36977(5) 0.0103(2) Uani 1 1 d . . . . .
P2 P 0.73188(12) 0.56300(6) 0.24064(5) 0.0102(2) Uani 1 1 d . . . . .
O1 O 0.7920(3) 0.74915(16) 0.42406(12) 0.0135(5) Uani 1 1 d . . . . .
O2 O 0.8685(4) 0.57314(17) 0.39806(13) 0.0161(6) Uani 1 1 d D . . . .
O3 O 1.0788(3) 0.70650(18) 0.34949(13) 0.0142(6) Uani 1 1 d . . . . .
O4 O 0.5607(3) 0.56228(18) 0.19337(13) 0.0150(6) Uani 1 1 d . . . . .
O5 O 0.9127(3) 0.55903(18) 0.19762(12) 0.0137(5) Uani 1 1 d . . . . .
O6 O 0.7257(4) 0.48275(16) 0.29707(13) 0.0168(6) Uani 1 1 d D . . . .
O7 O 0.5378(3) 0.69066(18) 0.31722(13) 0.0128(5) Uani 1 1 d D . . . .
O8 O 0.2766(4) 0.79310(18) 0.24141(15) 0.0186(6) Uani 1 1 d D . . . .
O9 O 0.3884(5) 0.7051(2) 0.11110(16) 0.0301(7) Uani 1 1 d D . . . .
N1 N 0.7619(5) 1.0422(2) 0.23197(16) 0.0131(6) Uani 1 1 d D . . . .
N2 N 0.3731(5) 0.7828(2) 0.43652(17) 0.0142(7) Uani 1 1 d D . . . .
N3 N 0.0852(4) 1.0155(2) 0.43693(16) 0.0134(7) Uani 1 1 d D . . . .
C1 C 0.7278(5) 0.6809(2) 0.29034(17) 0.0097(7) Uani 1 1 d . . . . .
C2 C 0.7735(5) 0.7640(2) 0.23875(18) 0.0114(7) Uani 1 1 d . . . . .
H2A H 0.9020 0.7533 0.2204 0.014 Uiso 1 1 calc R U . . .
H2B H 0.6860 0.7590 0.1985 0.014 Uiso 1 1 calc R U . . .
C3 C 0.7627(5) 0.8682(2) 0.26769(18) 0.0122(7) Uani 1 1 d . . . . .
H3A H 0.6464 0.8764 0.2956 0.015 Uiso 1 1 calc R U . . .
H3B H 0.8717 0.8811 0.2986 0.015 Uiso 1 1 calc R U . . .
C4 C 0.7630(5) 0.9393(2) 0.20678(18) 0.0131(7) Uani 1 1 d . . . . .
H4A H 0.8760 0.9280 0.1776 0.016 Uiso 1 1 calc R U . . .
H4B H 0.6508 0.9276 0.1772 0.016 Uiso 1 1 calc R U . . .
C5 C 0.3458(5) 0.8908(2) 0.4278(2) 0.0152(8) Uani 1 1 d . . . . .
H5A H 0.3621 0.9098 0.3781 0.018 Uiso 1 1 calc R U . . .
H5B H 0.4382 0.9273 0.4565 0.018 Uiso 1 1 calc R U . . .
C6 C 0.1473(5) 0.9131(2) 0.45211(19) 0.0133(8) Uani 1 1 d . . . . .
H6A H 0.0597 0.8670 0.4289 0.016 Uiso 1 1 calc R U . . .
H6B H 0.1393 0.9016 0.5033 0.016 Uiso 1 1 calc R U . . .
C7 C 0.2034(6) 1.0916(2) 0.4721(2) 0.0210(9) Uani 1 1 d . . . . .
H7A H 0.3357 1.0836 0.4571 0.025 Uiso 1 1 calc R U . . .
H7B H 0.1981 1.0818 0.5235 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1384(6) 1.1949(3) 0.4547(2) 0.0242(9) Uani 1 1 d . . . . .
H8A H 0.2192 1.2423 0.4787 0.036 Uiso 1 1 calc DR U . . .
H8B H 0.1458 1.2053 0.4039 0.036 Uiso 1 1 calc DR U . . .
H8C H 0.0082 1.2036 0.4703 0.036 Uiso 1 1 calc R U . . .
C9 C -0.1233(5) 1.0251(3) 0.4509(2) 0.0186(8) Uani 1 1 d . . . . .
H9A H -0.1900 0.9712 0.4267 0.022 Uiso 1 1 calc DR U . . .
H9B H -0.1684 1.0876 0.4307 0.022 Uiso 1 1 calc DR U . . .
C10 C -0.1731(6) 1.0225(3) 0.5282(2) 0.0308(10) Uani 1 1 d . . . . .
H10A H -0.3095 1.0289 0.5337 0.046 Uiso 1 1 calc R U . . .
H10B H -0.1319 0.9601 0.5485 0.046 Uiso 1 1 calc R U . . .
H10C H -0.1103 1.0766 0.5525 0.046 Uiso 1 1 calc R U . . .
H1N H 0.751(6) 1.087(2) 0.1976(17) 0.028(11) Uiso 1 1 d D . . . .
H2N H 0.868(5) 1.049(3) 0.2602(19) 0.029(12) Uiso 1 1 d D . . . .
H3N H 0.654(4) 1.048(3) 0.255(2) 0.023(11) Uiso 1 1 d D . . . .
H4N H 0.289(5) 0.748(3) 0.413(2) 0.028(12) Uiso 1 1 d D . . . .
H5N H 0.492(4) 0.765(3) 0.424(2) 0.019(11) Uiso 1 1 d D . . . .
H2 H 0.809(8) 0.542(4) 0.366(3) 0.013(17) Uiso 0.6 1 d D . P . .
H6 H 0.750(15) 0.505(7) 0.338(2) 0.02(3) Uiso 0.4 1 d D . P . .
H6N H 0.364(8) 0.765(4) 0.4835(15) 0.059(18) Uiso 1 1 d D . . . .
H7 H 0.481(5) 0.724(3) 0.2883(19) 0.021(12) Uiso 1 1 d D . . . .
H7N H 0.093(6) 1.027(3) 0.3897(13) 0.025(11) Uiso 1 1 d D . . . .
H8D H 0.282(7) 0.8533(19) 0.232(2) 0.032(13) Uiso 1 1 d D . . . .
H8E H 0.191(5) 0.783(3) 0.2719(18) 0.023(12) Uiso 1 1 d D . . . .
H9C H 0.433(9) 0.656(3) 0.135(3) 0.09(2) Uiso 1 1 d D . . . .
H9D H 0.329(7) 0.735(3) 0.144(2) 0.050(17) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.516(2) . ?
P1 O3 1.517(3) . ?
P1 O2 1.580(2) . ?
P1 C1 1.854(3) . ?
P2 O4 1.515(3) . ?
P2 O5 1.527(2) . ?
P2 O6 1.537(2) . ?
P2 C1 1.869(3) . ?
O7 C1 1.452(4) . ?
N1 C4 1.487(4) . ?
N2 C5 1.498(4) . ?
N3 C7 1.496(5) . ?
N3 C6 1.496(4) . ?
N3 C9 1.513(5) . ?
C1 C2 1.537(4) . ?
C2 C3 1.529(4) . ?
C3 C4 1.514(4) . ?
C5 C6 1.517(5) . ?
C7 C8 1.522(5) . ?
C9 C10 1.516(5) . ?

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 O3 114.77(14) . . ?
O1 P1 O2 108.68(13) . . ?
O3 P1 O2 109.75(14) . . ?
O1 P1 C1 109.12(15) . . ?
O3 P1 C1 109.66(15) . . ?
O2 P1 C1 104.34(14) . . ?
O4 P2 O5 110.96(13) . . ?
O4 P2 O6 112.87(15) . . ?
O5 P2 O6 112.01(15) . . ?
O4 P2 C1 107.13(15) . . ?
O5 P2 C1 108.43(15) . . ?
O6 P2 C1 105.05(14) . . ?
C7 N3 C6 113.4(3) . . ?
C7 N3 C9 114.4(3) . . ?
C6 N3 C9 109.6(3) . . ?
O7 C1 C2 110.8(3) . . ?
O7 C1 P1 104.4(2) . . ?
C2 C1 P1 113.3(2) . . ?
O7 C1 P2 105.8(2) . . ?
C2 C1 P2 108.0(2) . . ?
P1 C1 P2 114.21(17) . . ?
C3 C2 C1 116.5(3) . . ?
C4 C3 C2 108.7(3) . . ?
N1 C4 C3 111.1(3) . . ?
N2 C5 C6 106.5(3) . . ?
N3 C6 C5 113.8(3) . . ?
N3 C7 C8 112.1(3) . . ?
N3 C9 C10 113.5(3) . . ?

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
N1 H1N O3 0.90(2) 2.22(3) 2.955(4) 138(4) 4_755
N1 H1N O7 0.90(2) 2.51(4) 3.089(4) 123(3) 4_655
N1 H2N O5 0.93(2) 1.76(3) 2.686(4) 172(4) 4_755
N1 H3N O4 0.89(2) 1.82(2) 2.715(4) 177(4) 4_655
N2 H4N O3 0.88(2) 2.01(3) 2.868(4) 163(4) 1_455
N2 H5N O1 0.91(2) 2.14(3) 3.025(4) 162(4) .
N2 H5N O7 0.91(2) 2.30(4) 2.852(4) 119(3) .
N2 H6N O1 0.93(3) 1.85(3) 2.755(4) 165(5) 3_466
N3 H7N O5 0.92(2) 1.72(2) 2.633(4) 173(4) 4_655
O2 H2 O6 0.86(3) 1.65(3) 2.503(3) 170(7) .
O6 H6 O2 0.86(3) 1.70(5) 2.503(3) 156(10) .
O7 H7 O8 0.83(2) 1.95(3) 2.739(4) 161(4) .
O8 H8D O6 0.84(2) 1.85(3) 2.693(3) 174(5) 4_655
O8 H8E O3 0.85(2) 1.98(3) 2.761(4) 152(4) 1_455
O9 H9C O4 0.87(3) 1.93(3) 2.788(4) 170(6) .
O9 H9D O8 0.86(3) 2.06(3) 2.872(4) 158(5) .

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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 1553746'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C4 H11 N O7 P2), 2(C4 H14 N2), 7(H2 O)'
_chemical_formula_sum            'C16 H64 N6 O21 P4'
_chemical_formula_weight         800.61

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      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                   6.6881(3)
_cell_length_b                   14.5479(8)
_cell_length_c                   18.9197(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.223(5)
_cell_angle_gamma                90
_cell_volume                     1833.20(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3528
_cell_measurement_theta_min      2.1575
_cell_measurement_theta_max      32.2298

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_T_min  0.83529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            12581
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         32.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5900
_reflns_number_gt                4724
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0432P)²+0.8667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5900
_refine_ls_number_parameters     285
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 -0.07809(5) 0.37114(3) 0.15007(2) 0.01054(8) Uani 1 1 d . . . . .
P2 P -0.05778(5) 0.24713(2) 0.28364(2) 0.01018(8) Uani 1 1 d . . . . .
O1 O -0.08005(19) 0.27032(8) 0.11813(6) 0.0193(2) Uani 1 1 d D . . . .
O2 O -0.28680(16) 0.40995(9) 0.14296(6) 0.0189(2) Uani 1 1 d . . . . .
O3 O 0.07447(15) 0.42561(7) 0.11342(5) 0.0143(2) Uani 1 1 d . . . . .
O4 O 0.00005(16) 0.17386(7) 0.23062(6) 0.0148(2) Uani 1 1 d . . . . .
O5 O -0.28156(15) 0.24967(7) 0.29198(5) 0.0137(2) Uani 1 1 d . . . . .
O6 O 0.07115(16) 0.23913(7) 0.35424(5) 0.0143(2) Uani 1 1 d . . . . .
O7 O 0.23105(15) 0.35257(7) 0.25033(6) 0.0126(2) Uani 1 1 d D . . . .
O8 O 0.45123(17) 0.50092(9) 0.21332(7) 0.0242(3) Uani 1 1 d D . . . .
O9 O 0.39530(17) 0.32028(8) 0.07842(6) 0.0168(2) Uani 1 1 d D . . . .
O10 O -0.0262(3) 0.32160(10) 0.47804(8) 0.0343(3) Uani 1 1 d D . . . .
O11 O 0.1395(4) 0.4934(2) 0.50379(18) 0.0358(7) Uani 0.5 1 d D . P A -1
H11A H 0.074(7) 0.542(2) 0.511(3) 0.054 Uiso 0.5 1 d D U P B -1
H11B H 0.065(7) 0.446(2) 0.500(3) 0.054 Uiso 0.5 1 d D U P C -1
N1 N 0.07716(19) 0.69273(9) 0.30889(7) 0.0133(2) Uani 1 1 d D . . . .
N2 N 0.03884(19) 0.80538(9) 0.11292(7) 0.0138(2) Uani 1 1 d D . . . .
N3 N 0.1868(2) 0.59932(9) 0.09325(7) 0.0140(2) Uani 1 1 d D . . . .
C1 C 0.0139(2) 0.35836(9) 0.24510(7) 0.0101(2) Uani 1 1 d . . . . .
C2 C -0.0555(2) 0.43702(10) 0.29179(7) 0.0121(3) Uani 1 1 d . . . . .
H2A H -0.2036 0.4344 0.2911 0.015 Uiso 1 1 calc R U . . .
H2B H 0.0008 0.4263 0.3413 0.015 Uiso 1 1 calc R U . . .
C3 C 0.0042(2) 0.53362(10) 0.26979(7) 0.0130(3) Uani 1 1 d . . . . .
H3D H 0.1387 0.5313 0.2519 0.016 Uiso 1 1 calc R U . . .
H3E H -0.0926 0.5555 0.2307 0.016 Uiso 1 1 calc R U . . .
C4 C 0.0083(2) 0.60075(10) 0.33131(8) 0.0143(3) Uani 1 1 d . . . . .
H4A H -0.1277 0.6060 0.3476 0.017 Uiso 1 1 calc R U . . .
H4B H 0.1002 0.5777 0.3714 0.017 Uiso 1 1 calc R U . . .
C5 C -0.0047(2) 0.64519(11) 0.06603(8) 0.0182(3) Uani 1 1 d . . . . .
H5A H -0.1022 0.6390 0.1021 0.022 Uiso 1 1 calc R U . . .
H5B H -0.0609 0.6125 0.0228 0.022 Uiso 1 1 calc R U . . .
C6 C 0.0162(2) 0.74611(11) 0.04841(8) 0.0173(3) Uani 1 1 d . . . . .
H6A H 0.1347 0.7544 0.0213 0.021 Uiso 1 1 calc R U . . .
H6B H -0.1039 0.7660 0.0178 0.021 Uiso 1 1 calc R U . . .
C7 C 0.0242(3) 0.90511(12) 0.09516(10) 0.0255(4) Uani 1 1 d . . . . .
H7A H 0.1290 0.9214 0.0644 0.038 Uiso 1 1 calc R U . . .
H7B H 0.0419 0.9414 0.1389 0.038 Uiso 1 1 calc R U . . .
H7C H -0.1080 0.9181 0.0705 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3210(3) 0.57709(11) 0.03716(9) 0.0201(3) Uani 1 1 d . . . . .
H8A H 0.2485 0.5387 0.0008 0.030 Uiso 1 1 calc R U . . .
H8B H 0.4391 0.5438 0.0583 0.030 Uiso 1 1 calc R U . . .
H8C H 0.3639 0.6341 0.0155 0.030 Uiso 1 1 calc R U . . .
H1 H -0.062(4) 0.2335(16) 0.1540(11) 0.053(8) Uiso 1 1 d D . . . .
H1N H 0.091(3) 0.7294(11) 0.3468(9) 0.016(5) Uiso 1 1 d D . . . .
H2N H 0.193(3) 0.6874(15) 0.2906(10) 0.026(5) Uiso 1 1 d D . . . .
H3N H -0.016(3) 0.7169(13) 0.2743(9) 0.019(5) Uiso 1 1 d D . . . .
H4N H 0.160(2) 0.7966(15) 0.1344(10) 0.026(5) Uiso 1 1 d D . . . .
H5N H -0.060(2) 0.7920(13) 0.1409(9) 0.014(4) Uiso 1 1 d D . . . .
H6N H 0.260(3) 0.6343(13) 0.1245(9) 0.020(5) Uiso 1 1 d D . . . .
H7 H 0.283(3) 0.4021(12) 0.2366(11) 0.029(6) Uiso 1 1 d D . . . .
H7N H 0.153(3) 0.5457(11) 0.1120(10) 0.023(5) Uiso 1 1 d D . . . .
H8D H 0.482(3) 0.5528(13) 0.2334(12) 0.044(7) Uiso 1 1 d D . . . .
H8E H 0.558(3) 0.4807(16) 0.1956(12) 0.043(7) Uiso 1 1 d D . . . .
H9A H 0.500(3) 0.3530(13) 0.0942(12) 0.060(9) Uiso 1 1 d D . . . .
H9B H 0.299(3) 0.3502(16) 0.0919(14) 0.047(7) Uiso 1 1 d D . . . .
H10A H -0.012(4) 0.2947(17) 0.4397(10) 0.051(8) Uiso 1 1 d D . . . .
H10B H -0.044(4) 0.2796(14) 0.5069(11) 0.036(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.5004(11) . ?
P1 O3 1.5095(10) . ?
P1 O1 1.5860(12) . ?
P1 C1 1.8559(14) . ?
P2 O5 1.5197(11) . ?
P2 O6 1.5270(11) . ?
P2 O4 1.5371(11) . ?
P2 C1 1.8556(14) . ?
O7 C1 1.4492(16) . ?
N1 C4 1.4893(19) . ?
N2 C7 1.490(2) . ?
N2 C6 1.4908(19) . ?
N3 C8 1.4864(19) . ?
N3 C5 1.494(2) . ?
C1 C2 1.5426(19) . ?
C2 C3 1.5290(19) . ?
C3 C4 1.518(2) . ?
C5 C6 1.515(2) . ?

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 P1 O3 115.06(7) . . ?
O2 P1 O1 109.79(7) . . ?
O3 P1 O1 107.04(6) . . ?
O2 P1 C1 110.37(6) . . ?
O3 P1 C1 108.62(6) . . ?
O1 P1 C1 105.48(6) . . ?
O5 P2 O6 113.21(6) . . ?
O5 P2 O4 113.16(6) . . ?
O6 P2 O4 111.25(6) . . ?
O5 P2 C1 108.16(6) . . ?
O6 P2 C1 105.35(6) . . ?
O4 P2 C1 105.01(6) . . ?
C7 N2 C6 112.26(12) . . ?
C8 N3 C5 113.93(12) . . ?
O7 C1 C2 110.84(11) . . ?
O7 C1 P2 102.45(9) . . ?
C2 C1 P2 108.66(9) . . ?
O7 C1 P1 108.28(9) . . ?
C2 C1 P1 112.95(9) . . ?
P2 C1 P1 113.17(7) . . ?
C3 C2 C1 115.24(11) . . ?
C4 C3 C2 111.69(11) . . ?
N1 C4 C3 110.14(11) . . ?
N3 C5 C6 114.54(13) . . ?
N2 C6 C5 112.64(12) . . ?

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
O1 H1 O4 0.864(17) 1.709(17) 2.5647(16) 171(3) .
N1 H1N O9 0.892(14) 1.933(14) 2.8198(17) 172.8(18) 2
N1 H2N O4 0.882(15) 2.134(16) 3.0025(17) 167.9(19) 2
N1 H3N O5 0.929(15) 1.825(15) 2.7478(17) 171.8(18) 2_455
N2 H4N O6 0.882(15) 1.977(16) 2.7971(17) 154.1(19) 2
N2 H5N O5 0.907(14) 1.831(14) 2.7237(16) 167.5(18) 2_455
N3 H6N O6 0.892(15) 1.919(16) 2.7295(17) 150.3(18) 2
N3 H7N O3 0.894(15) 1.826(16) 2.6738(17) 157.6(19) .
O7 H7 O8 0.850(15) 1.903(16) 2.7394(16) 168(2) .
O8 H8D O4 0.862(16) 1.888(16) 2.7383(16) 169(2) 2
O8 H8E O2 0.866(15) 1.822(16) 2.6491(16) 159(2) 1_655
O9 H9A O2 0.877(16) 1.825(17) 2.6909(16) 169.1(19) 1_655
O9 H9B O3 0.838(16) 1.931(16) 2.7658(15) 174(3) .
O10 H10A O6 0.836(16) 1.935(17) 2.7617(17) 169(3) .
O10 H10B O9 0.835(16) 2.052(16) 2.8851(18) 176(2) 4_566
O11 H11A O10 0.852(19) 2.02(3) 2.825(3) 157(5) 3_566
O11 H11B O10 0.845(19) 1.95(2) 2.759(3) 160(5) .

_refine_diff_density_max         0.501
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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 1553745'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O7 P2, C3 H12 N2, 3(H2 O)'
_chemical_formula_sum            'C7 H29 N3 O10 P2'
_chemical_formula_weight         377.27

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'
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      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                   6.5601(2)
_cell_length_b                   14.3307(4)
_cell_length_c                   17.7022(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.825(2)
_cell_angle_gamma                90
_cell_volume                     1663.35(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7591
_cell_measurement_theta_min      2.2975
_cell_measurement_theta_max      32.3665

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_T_min  0.96720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            19608
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         32.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5424
_reflns_number_gt                4525
_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       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0354P)²+0.7865P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5424
_refine_ls_number_parameters     263
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_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_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 0.25993(5) 0.18096(2) 0.32201(2) 0.00819(7) Uani 1 1 d . . . . .
P2 P 0.21119(5) 0.26414(2) 0.16323(2) 0.00877(7) Uani 1 1 d . . . . .
O1 O 0.38988(14) 0.11273(7) 0.36719(5) 0.01248(19) Uani 1 1 d . . . . .
O2 O 0.03295(14) 0.16898(7) 0.33508(5) 0.01099(18) Uani 1 1 d . . . . .
O3 O 0.33129(15) 0.28313(7) 0.33591(5) 0.01294(19) Uani 1 1 d . . . . .
O4 O -0.01841(14) 0.26474(7) 0.16146(6) 0.01274(19) Uani 1 1 d . . . . .
O5 O 0.29767(15) 0.35158(7) 0.20734(6) 0.0142(2) Uani 1 1 d D . . . .
O6 O 0.30519(15) 0.25957(7) 0.08640(5) 0.01264(19) Uani 1 1 d . . . . .
O7 O 0.52333(14) 0.16683(7) 0.21092(5) 0.01057(18) Uani 1 1 d D . . . .
O9 O 0.2031(2) 0.12916(9) -0.02895(7) 0.0254(3) Uani 1 1 d D . . . .
O8 O 0.77907(15) 0.03811(8) 0.26712(6) 0.0171(2) Uani 1 1 d D . . . .
O10 O 0.79326(16) 0.58373(7) -0.00124(6) 0.0145(2) Uani 1 1 d D . . . .
N1 N 0.22612(18) -0.18952(8) 0.20923(7) 0.0128(2) Uani 1 1 d D . . . .
N2 N 0.70129(18) 0.19372(8) 0.06295(6) 0.0116(2) Uani 1 1 d D . . . .
N3 N 0.75747(18) 0.40641(8) -0.05861(7) 0.0112(2) Uani 1 1 d D . . . .
C1 C 0.1693(2) -0.09635(9) 0.17822(8) 0.0126(2) Uani 1 1 d . . . . .
H1A H 0.0199 -0.0880 0.1810 0.015 Uiso 1 1 calc R U . . .
H1B H 0.2048 -0.0937 0.1243 0.015 Uiso 1 1 calc R U . . .
C2 C 0.2754(2) -0.01743(9) 0.22033(8) 0.0128(2) Uani 1 1 d . . . . .
H2A H 0.4251 -0.0252 0.2183 0.015 Uiso 1 1 calc R U . . .
H2B H 0.2374 -0.0182 0.2740 0.015 Uiso 1 1 calc R U . . .
C3 C 0.21223(19) 0.07540(9) 0.18405(7) 0.0096(2) Uani 1 1 d . . . . .
H3A H 0.0620 0.0807 0.1856 0.011 Uiso 1 1 calc R U . . .
H3B H 0.2483 0.0736 0.1302 0.011 Uiso 1 1 calc R U . . .
C4 C 0.30590(19) 0.16360(9) 0.21958(7) 0.0083(2) Uani 1 1 d . . . . .
C5 C 0.7146(2) 0.09140(10) 0.05075(9) 0.0173(3) Uani 1 1 d . . . . .
H5A H 0.6956 0.0589 0.0987 0.026 Uiso 1 1 calc R U . . .
H5B H 0.6082 0.0720 0.0139 0.026 Uiso 1 1 calc R U . . .
H5C H 0.8488 0.0758 0.0315 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7285(2) 0.24858(9) -0.00709(7) 0.0123(2) Uani 1 1 d . . . . .
H6A H 0.6149 0.2355 -0.0437 0.015 Uiso 1 1 calc R U . . .
H6B H 0.8577 0.2304 -0.0305 0.015 Uiso 1 1 calc R U . . .
C7 C 0.7328(2) 0.35195(9) 0.01187(7) 0.0115(2) Uani 1 1 d . . . . .
H7A H 0.6043 0.3700 0.0358 0.014 Uiso 1 1 calc R U . . .
H7B H 0.8476 0.3653 0.0479 0.014 Uiso 1 1 calc R U . . .
H1N H 0.357(2) -0.2035(16) 0.2027(13) 0.038(6) Uiso 1 1 d D . . . .
H2N H 0.195(3) -0.1927(15) 0.2583(9) 0.026(5) Uiso 1 1 d D . . . .
H3N H 0.149(3) -0.2359(12) 0.1872(11) 0.024(5) Uiso 1 1 d D . . . .
H4N H 0.797(2) 0.2105(13) 0.0970(10) 0.018(5) Uiso 1 1 d D . . . .
H5N H 0.580(2) 0.2079(14) 0.0802(11) 0.024(5) Uiso 1 1 d D . . . .
H6N H 0.772(3) 0.4679(11) -0.0476(11) 0.023(5) Uiso 1 1 d D . . . .
H7N H 0.868(2) 0.3870(13) -0.0847(10) 0.017(4) Uiso 1 1 d D . . . .
H8N H 0.646(2) 0.4021(13) -0.0886(10) 0.019(5) Uiso 1 1 d D . . . .
H5 H 0.315(4) 0.3352(19) 0.2550(10) 0.063(8) Uiso 1 1 d D . . . .
H7 H 0.580(3) 0.1213(13) 0.2336(11) 0.028(5) Uiso 1 1 d D . . . .
H9A H 0.242(3) 0.1541(15) -0.0695(10) 0.037(6) Uiso 1 1 d D . . . .
H9B H 0.235(3) 0.1683(14) 0.0045(10) 0.032(6) Uiso 1 1 d D . . . .
H8A H 0.874(3) 0.0679(15) 0.2901(13) 0.047(7) Uiso 1 1 d D . . . .
H8B H 0.767(3) -0.0162(12) 0.2856(13) 0.047(7) Uiso 1 1 d D . . . .
H10A H 0.757(3) 0.6300(12) -0.0271(11) 0.028(5) Uiso 1 1 d D . . . .
H10B H 0.737(3) 0.5910(15) 0.0418(9) 0.035(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.5096(10) . ?
P1 O2 1.5238(10) . ?
P1 O3 1.5544(10) . ?
P1 C4 1.8643(13) . ?
P2 O4 1.5056(10) . ?
P2 O6 1.5126(10) . ?
P2 O5 1.5727(10) . ?
P2 C4 1.8487(13) . ?
O7 C4 1.4402(15) . ?
N1 C1 1.4865(17) . ?
N2 C6 1.4837(17) . ?
N2 C5 1.4850(18) . ?
N3 C7 1.4849(17) . ?
C1 C2 1.5121(18) . ?
C2 C3 1.5287(18) . ?
C3 C4 1.5316(17) . ?
C6 C7 1.5190(19) . ?

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 O2 112.62(6) . . ?
O1 P1 O3 111.35(6) . . ?
O2 P1 O3 111.89(5) . . ?
O1 P1 C4 108.83(6) . . ?
O2 P1 C4 108.77(5) . . ?
O3 P1 C4 102.86(6) . . ?
O4 P2 O6 114.70(6) . . ?
O4 P2 O5 110.53(6) . . ?
O6 P2 O5 109.27(6) . . ?
O4 P2 C4 109.54(6) . . ?
O6 P2 C4 108.17(6) . . ?
O5 P2 C4 104.09(6) . . ?
C6 N2 C5 113.10(11) . . ?
N1 C1 C2 112.56(11) . . ?
C1 C2 C3 109.24(10) . . ?
C2 C3 C4 116.47(10) . . ?
O7 C4 C3 111.63(10) . . ?
O7 C4 P2 103.56(8) . . ?
C3 C4 P2 107.34(8) . . ?
O7 C4 P1 106.90(8) . . ?
C3 C4 P1 115.74(9) . . ?
P2 C4 P1 111.03(7) . . ?
N2 C6 C7 109.51(11) . . ?
N3 C7 C6 109.19(11) . . ?

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
N1 H1N O3 0.894(15) 2.183(16) 3.0611(16) 167(2) 2_645
N1 H2N O4 0.900(15) 1.960(17) 2.7793(16) 150.7(18) 2_545
N1 H3N O2 0.916(15) 1.845(15) 2.7443(15) 166.6(19) 2_545
N2 H5N O6 0.886(15) 1.954(15) 2.8077(15) 161.4(19) .
N2 H4N O4 0.891(14) 1.811(15) 2.6933(15) 170.2(18) 1_655
N3 H6N O10 0.907(15) 1.855(15) 2.7437(15) 166.0(18) .
N3 H7N O2 0.916(14) 1.981(15) 2.8621(15) 160.7(16) 4_665
N3 H8N O1 0.893(14) 1.842(14) 2.7229(14) 168.5(18) 4_565
O5 H5 O3 0.879(17) 1.616(18) 2.4818(14) 168(3) .
O7 H7 O8 0.845(15) 1.853(16) 2.6648(14) 161(2) .
O8 H8A O2 0.849(16) 1.940(17) 2.7588(14) 162(2) 1_655
O8 H8B O5 0.850(16) 1.946(17) 2.7600(14) 160(2) 2_645
O9 H9B O6 0.837(15) 1.996(15) 2.8326(16) 178(2) .
O9 H9A O3 0.847(15) 2.006(16) 2.8526(16) 178(2) 4_565
O10 H10B O1 0.864(15) 1.862(15) 2.7257(14) 177(2) 2_655
O10 H10A O6 0.836(15) 1.935(15) 2.7695(14) 176(2) 3_665

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1553752'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O7 P2, 2(C3 H7 N6), 7(H2 O)'
_chemical_formula_sum            'C10 H39 N13 O14 P2'
_chemical_formula_weight         627.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   16.4593(3)
_cell_length_b                   12.5327(3)
_cell_length_c                   12.4717(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.612(2)
_cell_angle_gamma                90
_cell_volume                     2571.64(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4890
_cell_measurement_theta_min      2.6835
_cell_measurement_theta_max      66.3833

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.363
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_T_min  0.81485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3988
_diffrn_reflns_number            13792
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.686
_diffrn_reflns_theta_max         66.490
_diffrn_reflns_theta_full        66.490
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4505
_reflns_number_gt                3888
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0427P)²+0.8192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4505
_refine_ls_number_parameters     484
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_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_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 0.80238(2) 0.01847(3) 0.23333(3) 0.01131(11) Uani 1 1 d . . . . .
P2 P 0.80414(2) 0.01527(3) 0.48353(3) 0.01148(11) Uani 1 1 d . . . . .
O1 O 0.73946(7) 0.10713(10) 0.24178(9) 0.0152(3) Uani 1 1 d . . . . .
O2 O 0.76571(7) -0.09232(9) 0.22216(9) 0.0150(2) Uani 1 1 d . . . . .
O3 O 0.86245(7) 0.04293(10) 0.14493(9) 0.0147(2) Uani 1 1 d . . . . .
O4 O 0.76191(7) 0.12201(10) 0.49489(9) 0.0153(3) Uani 1 1 d . . . . .
O5 O 0.75243(7) -0.08282(10) 0.48324(9) 0.0146(2) Uani 1 1 d . . . . .
O6 O 0.86957(7) 0.01115(10) 0.57902(9) 0.0160(3) Uani 1 1 d D . . . .
H6 H 0.8860(15) -0.0521(16) 0.591(2) 0.042(7) Uiso 1 1 d D . . . .
O7 O 0.89724(7) 0.13388(9) 0.36251(9) 0.0147(3) Uani 1 1 d D . . . .
H7 H 0.8581(12) 0.1756(17) 0.3683(18) 0.026(6) Uiso 1 1 d D . . . .
O8 O 0.76836(8) 0.31899(11) 0.21007(10) 0.0214(3) Uani 1 1 d D . . . .
H8A H 0.7625(16) 0.2507(14) 0.217(2) 0.042(7) Uiso 1 1 d D . . . .
H8B H 0.7679(14) 0.3344(18) 0.1426(14) 0.028(6) Uiso 1 1 d D . . . .
O9 O 0.77431(9) 0.34625(11) 0.48654(11) 0.0256(3) Uani 1 1 d D . . . .
H9A H 0.775(2) 0.2778(14) 0.494(2) 0.063(9) Uiso 1 1 d D . . . .
H9B H 0.7991(15) 0.374(2) 0.5426(17) 0.041(7) Uiso 1 1 d D . . . .
O10 O 0.88288(8) 0.42226(12) 0.34073(11) 0.0275(3) Uani 1 1 d D . . . .
H10A H 0.8502(16) 0.401(2) 0.3905(18) 0.053(8) Uiso 1 1 d D . . . .
H10B H 0.8596(16) 0.398(2) 0.2831(16) 0.052(8) Uiso 1 1 d D . . . .
O11 O 0.78692(9) 0.61529(13) 0.32810(12) 0.0327(3) Uani 1 1 d D . . . .
H11A H 0.8149(16) 0.5570(18) 0.330(2) 0.051(8) Uiso 1 1 d D . . . .
H11B H 0.7902(18) 0.641(2) 0.3927(17) 0.055(9) Uiso 1 1 d D . . . .
O12 O 1.04056(8) 0.38387(11) 0.42393(10) 0.0197(3) Uani 1 1 d D . . . .
H12A H 0.9963(11) 0.398(2) 0.391(2) 0.042(7) Uiso 1 1 d D . . . .
H12B H 1.0751(11) 0.4292(16) 0.4018(17) 0.022(5) Uiso 1 1 d D . . . .
O13 O 1.05993(8) 0.17066(11) 0.36484(10) 0.0209(3) Uani 1 1 d D . . . .
H13A H 1.0076(11) 0.159(2) 0.369(2) 0.057(9) Uiso 1 1 d D . . . .
H13B H 1.0685(17) 0.2373(16) 0.385(2) 0.052(8) Uiso 1 1 d D . . . .
O14 O 0.77918(8) -0.20342(11) 0.03301(10) 0.0222(3) Uani 1 1 d D . . . .
H14A H 0.7848(16) -0.184(2) 0.0997(15) 0.044(7) Uiso 1 1 d D . . . .
H14B H 0.7733(19) -0.2706(15) 0.030(2) 0.056(9) Uiso 1 1 d D . . . .
N1 N 0.99208(9) -0.34340(12) 0.36077(12) 0.0157(3) Uani 1 1 d D . . . .
H1N H 1.0398(11) -0.3761(18) 0.3530(18) 0.024(6) Uiso 1 1 d D . . . .
H2N H 0.9725(12) -0.3635(17) 0.4234(14) 0.017(5) Uiso 1 1 d D . . . .
H3N H 0.9574(12) -0.3622(17) 0.3091(15) 0.019(5) Uiso 1 1 d D . . . .
N2 N 0.58502(9) 0.13059(12) 0.13707(11) 0.0147(3) Uani 1 1 d D . . . .
H4N H 0.6383(10) 0.1250(19) 0.1433(18) 0.024(6) Uiso 1 1 d D . . . .
H5N H 0.5593(12) 0.1290(18) 0.0742(14) 0.022(5) Uiso 1 1 d D . . . .
N3 N 0.59429(9) 0.12678(12) 0.50498(12) 0.0160(3) Uani 1 1 d D . . . .
H6N H 0.6486(10) 0.124(2) 0.4992(19) 0.031(6) Uiso 1 1 d D . . . .
H7N H 0.5700(12) 0.1257(17) 0.5667(14) 0.015(5) Uiso 1 1 d D . . . .
N4 N 0.34860(9) 0.10594(12) 0.32436(12) 0.0164(3) Uani 1 1 d D . . . .
H8N H 0.3259(12) 0.1006(17) 0.3881(13) 0.015(5) Uiso 1 1 d D . . . .
H9N H 0.3193(12) 0.1089(17) 0.2647(14) 0.019(5) Uiso 1 1 d D . . . .
N5 N 0.58855(8) 0.12382(11) 0.32053(11) 0.0138(3) Uani 1 1 d D . . . .
H16N H 0.6436(10) 0.1208(19) 0.3154(18) 0.027(6) Uiso 1 1 d D . . . .
N6 N 0.46900(8) 0.11847(12) 0.41816(11) 0.0145(3) Uani 1 1 d . . . . .
N7 N 0.46301(8) 0.12288(11) 0.22448(11) 0.0134(3) Uani 1 1 d . . . . .
N8 N 0.38450(9) 0.11710(13) -0.00187(11) 0.0170(3) Uani 1 1 d D . . . .
H10N H 0.3318(10) 0.1327(18) -0.0069(17) 0.022(5) Uiso 1 1 d D . . . .
H11N H 0.4075(13) 0.1172(18) 0.0636(14) 0.022(5) Uiso 1 1 d D . . . .
N9 N 0.63092(9) 0.11640(12) -0.16515(12) 0.0158(3) Uani 1 1 d D . . . .
H12N H 0.6524(12) 0.1150(17) -0.0997(13) 0.019(5) Uiso 1 1 d D . . . .
H13N H 0.6614(12) 0.1248(18) -0.2213(15) 0.024(6) Uiso 1 1 d D . . . .
N10 N 0.39386(9) 0.13327(12) -0.36886(12) 0.0158(3) Uani 1 1 d D . . . .
H14N H 0.4188(12) 0.1287(17) -0.4308(14) 0.016(5) Uiso 1 1 d D . . . .
H15N H 0.3384(10) 0.1266(19) -0.3708(18) 0.026(6) Uiso 1 1 d D . . . .
N11 N 0.50999(8) 0.11613(12) -0.07944(11) 0.0140(3) Uani 1 1 d . . . . .
N12 N 0.51573(8) 0.12664(11) -0.27254(11) 0.0135(3) Uani 1 1 d . . . . .
N13 N 0.39027(8) 0.12592(12) -0.18557(11) 0.0137(3) Uani 1 1 d D . . . .
H17N H 0.3361(11) 0.115(2) -0.194(2) 0.043(7) Uiso 1 1 d D . . . .
C1 C 0.86361(9) 0.02565(13) 0.36066(13) 0.0124(3) Uani 1 1 d . . . . .
C2 C 0.93825(9) -0.04695(14) 0.36077(13) 0.0130(3) Uani 1 1 d . . . . .
H2A H 0.9699 -0.0294 0.2968 0.016 Uiso 1 1 calc R U . . .
H2B H 0.9727 -0.0293 0.4247 0.016 Uiso 1 1 calc R U . . .
C3 C 0.92323(10) -0.16717(14) 0.36094(13) 0.0143(3) Uani 1 1 d . . . . .
H3A H 0.8930 -0.1874 0.4254 0.017 Uiso 1 1 calc R U . . .
H3B H 0.8901 -0.1875 0.2967 0.017 Uiso 1 1 calc R U . . .
C4 C 1.00420(10) -0.22530(14) 0.36076(13) 0.0155(3) Uani 1 1 d . . . . .
H4A H 1.0343 -0.2043 0.2964 0.019 Uiso 1 1 calc R U . . .
H4B H 1.0372 -0.2044 0.4249 0.019 Uiso 1 1 calc R U . . .
C5 C 0.54394(10) 0.12584(13) 0.22618(13) 0.0120(3) Uani 1 1 d . . . . .
C6 C 0.54965(10) 0.12258(13) 0.41574(13) 0.0131(3) Uani 1 1 d . . . . .
C7 C 0.42860(10) 0.11561(13) 0.32182(13) 0.0132(3) Uani 1 1 d . . . . .
C8 C 0.42950(10) 0.11988(13) -0.08797(13) 0.0138(3) Uani 1 1 d . . . . .
C9 C 0.55039(10) 0.11944(13) -0.17262(13) 0.0130(3) Uani 1 1 d . . . . .
C10 C 0.43446(10) 0.12866(13) -0.27600(13) 0.0125(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
P1 O2 1.5189(12) . ?
P1 O1 1.5246(12) . ?
P1 O3 1.5323(12) . ?
P1 C1 1.8588(16) . ?
P2 O5 1.4952(12) . ?
P2 O4 1.5161(12) . ?
P2 O6 1.5838(12) . ?
P2 C1 1.8460(17) . ?
O7 C1 1.465(2) . ?
N1 C4 1.494(2) . ?
N2 C5 1.318(2) . ?
N3 C6 1.317(2) . ?
N4 C7 1.324(2) . ?
N5 C6 1.365(2) . ?
N5 C5 1.370(2) . ?
N6 C6 1.330(2) . ?
N6 C7 1.357(2) . ?
N7 C5 1.332(2) . ?
N7 C7 1.357(2) . ?
N8 C8 1.322(2) . ?
N9 C9 1.327(2) . ?
N10 C10 1.322(2) . ?
N11 C8 1.327(2) . ?
N11 C9 1.356(2) . ?
N12 C10 1.337(2) . ?
N12 C9 1.359(2) . ?
N13 C10 1.360(2) . ?
N13 C8 1.364(2) . ?
C1 C2 1.529(2) . ?
C2 C3 1.527(2) . ?
C3 C4 1.519(2) . ?

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 P1 O1 113.80(6) . . ?
O2 P1 O3 112.31(7) . . ?
O1 P1 O3 110.93(7) . . ?
O2 P1 C1 109.09(7) . . ?
O1 P1 C1 104.99(7) . . ?
O3 P1 C1 105.06(7) . . ?
O5 P2 O4 117.60(7) . . ?
O5 P2 O6 110.49(7) . . ?
O4 P2 O6 105.21(7) . . ?
O5 P2 C1 111.78(7) . . ?
O4 P2 C1 105.70(7) . . ?
O6 P2 C1 105.15(7) . . ?
C6 N5 C5 119.63(14) . . ?
C6 N6 C7 116.45(14) . . ?
C5 N7 C7 115.46(14) . . ?
C8 N11 C9 116.29(14) . . ?
C10 N12 C9 115.13(14) . . ?
C10 N13 C8 119.39(14) . . ?
O7 C1 C2 104.34(12) . . ?
O7 C1 P2 105.13(10) . . ?
C2 C1 P2 113.71(11) . . ?
O7 C1 P1 104.70(10) . . ?
C2 C1 P1 112.85(11) . . ?
P2 C1 P1 114.74(8) . . ?
C3 C2 C1 117.21(13) . . ?
C4 C3 C2 109.34(13) . . ?
N1 C4 C3 110.99(14) . . ?
N2 C5 N7 121.61(15) . . ?
N2 C5 N5 116.73(14) . . ?
N7 C5 N5 121.66(15) . . ?
N3 C6 N6 121.05(15) . . ?
N3 C6 N5 118.06(15) . . ?
N6 C6 N5 120.88(14) . . ?
N4 C7 N7 117.91(14) . . ?
N4 C7 N6 116.37(15) . . ?
N7 C7 N6 125.72(15) . . ?
N8 C8 N11 120.99(15) . . ?
N8 C8 N13 117.67(15) . . ?
N11 C8 N13 121.34(15) . . ?
N9 C9 N11 116.88(14) . . ?
N9 C9 N12 117.34(15) . . ?
N11 C9 N12 125.78(15) . . ?
N10 C10 N12 120.64(15) . . ?
N10 C10 N13 117.30(15) . . ?
N12 C10 N13 122.06(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6 O13 0.850(18) 1.809(18) 2.6426(18) 166(3) 3_756
O7 H7 O4 0.834(16) 2.36(2) 2.8136(17) 114.4(19) .
O8 H8A O1 0.866(17) 1.866(17) 2.7282(18) 174(3) .
O8 H8B O4 0.863(16) 1.921(16) 2.7828(17) 176(2) 4_565
O9 H9A O4 0.863(18) 1.964(18) 2.8200(19) 171(3) .
O9 H9B O3 0.870(17) 1.933(18) 2.7882(17) 167(3) 4_566
O10 H10A O9 0.876(17) 1.882(18) 2.755(2) 174(3) .
O10 H10B O8 0.859(17) 2.00(2) 2.7768(18) 150(3) .
O11 H11A O10 0.864(18) 2.028(18) 2.891(2) 177(3) .
O11 H11B O14 0.869(17) 1.929(18) 2.790(2) 171(3) 4_566
O12 H12A O10 0.844(17) 1.977(17) 2.8093(18) 169(2) .
O12 H12B O3 0.854(16) 1.861(17) 2.7087(17) 171(2) 2_755
O13 H13A O7 0.876(17) 1.844(18) 2.7164(17) 174(3) .
O13 H13B O12 0.882(17) 1.96(2) 2.7926(19) 157(3) .
O14 H14A O2 0.868(17) 1.947(19) 2.7536(17) 154(3) .
O14 H14B O5 0.848(18) 1.956(18) 2.7822(18) 164(3) 4
N1 H1N O3 0.894(16) 1.901(17) 2.7887(19) 172(2) 2_745
N1 H2N O12 0.890(16) 1.939(17) 2.800(2) 162.2(19) 3_756
N1 H3N O13 0.880(16) 2.219(19) 2.9232(19) 136.8(18) 2_745
N2 H4N O1 0.881(16) 2.053(18) 2.8402(18) 148(2) .
N2 H5N N11 0.880(16) 2.067(17) 2.943(2) 174(2) .
N3 H6N O4 0.900(17) 1.867(17) 2.7659(18) 177(2) .
N3 H7N N12 0.877(16) 2.218(16) 3.094(2) 176.5(19) 1_556
N4 H8N O5 0.890(15) 2.098(16) 2.9717(19) 166.7(18) 3_656
N4 H9N O11 0.875(16) 2.072(17) 2.892(2) 155.8(19) 2_645
N5 H16N O1 0.911(16) 1.855(18) 2.7047(18) 154(2) .
N8 H10N O14 0.890(16) 2.048(17) 2.919(2) 166(2) 3_655
N8 H11N N7 0.890(16) 2.182(16) 3.072(2) 178(2) .
N9 H12N O9 0.881(16) 2.301(18) 3.0194(19) 138.7(18) 4_565
N9 H13N O8 0.879(16) 2.101(18) 2.897(2) 150(2) 4_565
N10 H14N N6 0.886(16) 2.082(16) 2.967(2) 175.8(18) 1_554
N10 H15N O5 0.916(16) 2.095(19) 2.8353(18) 137.1(19) 3_655
N13 H17N O2 0.905(17) 1.726(18) 2.6288(17) 175(3) 3_655

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1553744'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O7 P2, C2 H10 N2, 2(H2 O)'
_chemical_formula_sum            'C6 H25 N3 O9 P2'
_chemical_formula_weight         345.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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+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                   8.8351(2)
_cell_length_b                   11.5516(3)
_cell_length_c                   28.2122(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2879.32(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5129
_cell_measurement_theta_min      5.9090
_cell_measurement_theta_max      66.8570

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.215
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.72600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            10800
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         5.910
_diffrn_reflns_theta_max         66.868
_diffrn_reflns_theta_full        66.868
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2559
_reflns_number_gt                2354
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0405P)²+1.2805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2559
_refine_ls_number_parameters     241
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.063
_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_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 0.22335(4) 0.13384(3) 0.38011(2) 0.00731(11) Uani 1 1 d . . . . .
P2 P 0.53468(4) 0.18043(3) 0.33576(2) 0.00809(11) Uani 1 1 d . . . . .
O1 O 0.19017(12) 0.10196(9) 0.32810(3) 0.0115(2) Uani 1 1 d . . . . .
O2 O 0.09291(11) 0.20239(9) 0.40152(4) 0.0111(2) Uani 1 1 d . . . . .
O3 O 0.26625(12) 0.02873(8) 0.40974(3) 0.0103(2) Uani 1 1 d . . . . .
O4 O 0.43916(12) 0.14452(9) 0.29045(4) 0.0116(2) Uani 1 1 d D . . . .
O5 O 0.63938(11) 0.27774(9) 0.32120(4) 0.0112(2) Uani 1 1 d . . . . .
O6 O 0.61220(12) 0.07767(9) 0.35785(4) 0.0123(2) Uani 1 1 d . . . . .
O7 O 0.33328(12) 0.33974(9) 0.35475(3) 0.0098(2) Uani 1 1 d D . . . .
O8 O 0.02083(13) 0.39406(10) 0.45331(4) 0.0172(2) Uani 1 1 d D . . . .
O9 O 0.81165(13) 0.13200(9) 0.43059(4) 0.0148(2) Uani 1 1 d D . . . .
N1 N 0.73797(15) 0.44607(11) 0.49091(4) 0.0109(3) Uani 1 1 d D . . . .
N2 N -0.06815(15) 0.34360(12) 0.33937(4) 0.0112(3) Uani 1 1 d D . . . .
N3 N 0.00125(15) 0.46507(11) 0.21857(4) 0.0111(3) Uani 1 1 d D . . . .
C1 C 0.38722(16) 0.23494(12) 0.37677(5) 0.0082(3) Uani 1 1 d . . . . .
C2 C 0.44843(17) 0.25590(13) 0.42701(5) 0.0100(3) Uani 1 1 d . . . . .
H2A H 0.3624 0.2768 0.4478 0.012 Uiso 1 1 calc R U . . .
H2B H 0.4911 0.1823 0.4390 0.012 Uiso 1 1 calc R U . . .
C3 C 0.56947(17) 0.34980(13) 0.43151(5) 0.0108(3) Uani 1 1 d . . . . .
H3A H 0.6575 0.3305 0.4113 0.013 Uiso 1 1 calc R U . . .
H3B H 0.5282 0.4252 0.4210 0.013 Uiso 1 1 calc R U . . .
C4 C 0.61810(17) 0.35725(12) 0.48298(5) 0.0117(3) Uani 1 1 d . . . . .
H4A H 0.5290 0.3763 0.5028 0.014 Uiso 1 1 calc R U . . .
H4B H 0.6565 0.2807 0.4933 0.014 Uiso 1 1 calc R U . . .
C5 C 0.01261(18) 0.35572(13) 0.29348(5) 0.0123(3) Uani 1 1 d . . . . .
H5A H 0.0434 0.2784 0.2818 0.015 Uiso 1 1 calc R U . . .
H5B H 0.1051 0.4029 0.2980 0.015 Uiso 1 1 calc R U . . .
C6 C -0.09038(17) 0.41358(13) 0.25734(5) 0.0116(3) Uani 1 1 d . . . . .
H6A H -0.1613 0.3557 0.2440 0.014 Uiso 1 1 calc R U . . .
H6B H -0.1506 0.4748 0.2730 0.014 Uiso 1 1 calc R U . . .
H1N H 0.748(2) 0.4566(17) 0.5226(6) 0.024(5) Uiso 1 1 d D . . . .
H2N H 0.8306(19) 0.4221(18) 0.4797(7) 0.028(5) Uiso 1 1 d D . . . .
H3N H 0.714(2) 0.5137(14) 0.4758(6) 0.016(5) Uiso 1 1 d D . . . .
H4 H 0.349(2) 0.128(2) 0.3000(9) 0.045(7) Uiso 1 1 d D . . . .
H4N H -0.079(2) 0.4153(14) 0.3504(7) 0.018(5) Uiso 1 1 d D . . . .
H5N H -0.014(2) 0.2996(17) 0.3595(7) 0.030(6) Uiso 1 1 d D . . . .
H6N H -0.161(2) 0.3133(17) 0.3341(7) 0.026(5) Uiso 1 1 d D . . . .
H7 H 0.299(3) 0.3857(18) 0.3756(7) 0.032(6) Uiso 1 1 d D . . . .
H7N H 0.055(2) 0.4074(15) 0.2034(7) 0.023(5) Uiso 1 1 d D . . . .
H8A H 0.042(3) 0.3294(15) 0.4409(8) 0.039(7) Uiso 1 1 d D . . . .
H8B H 0.067(2) 0.4463(16) 0.4373(8) 0.032(6) Uiso 1 1 d D . . . .
H8N H -0.062(2) 0.5022(17) 0.1975(7) 0.028(5) Uiso 1 1 d D . . . .
H9A H 0.753(2) 0.1143(19) 0.4078(7) 0.032(6) Uiso 1 1 d D . . . .
H9B H 0.899(2) 0.149(2) 0.4196(8) 0.035(6) Uiso 1 1 d D . . . .
H9N H 0.066(2) 0.5198(16) 0.2308(7) 0.025(5) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.5220(10) . ?
P1 O2 1.5231(10) . ?
P1 O1 1.5411(10) . ?
P1 C1 1.8625(15) . ?
P2 O6 1.5056(11) . ?
P2 O5 1.5126(11) . ?
P2 O4 1.5868(11) . ?
P2 C1 1.8527(15) . ?
O7 C1 1.4418(17) . ?
N1 C4 1.4915(19) . ?
N2 C5 1.4848(19) . ?
N3 C6 1.4852(19) . ?
C1 C2 1.5362(19) . ?
C2 C3 1.528(2) . ?
C3 C4 1.517(2) . ?
C5 C6 1.521(2) . ?

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 O2 112.67(6) . . ?
O3 P1 O1 112.31(6) . . ?
O2 P1 O1 110.97(6) . . ?
O3 P1 C1 109.54(6) . . ?
O2 P1 C1 106.40(6) . . ?
O1 P1 C1 104.45(6) . . ?
O6 P2 O5 114.84(6) . . ?
O6 P2 O4 111.68(6) . . ?
O5 P2 O4 107.50(6) . . ?
O6 P2 C1 109.22(6) . . ?
O5 P2 C1 110.31(6) . . ?
O4 P2 C1 102.59(6) . . ?
O7 C1 C2 112.43(11) . . ?
O7 C1 P2 104.40(9) . . ?
C2 C1 P2 112.47(10) . . ?
O7 C1 P1 106.94(9) . . ?
C2 C1 P1 109.01(9) . . ?
P2 C1 P1 111.42(7) . . ?
C3 C2 C1 115.78(12) . . ?
C4 C3 C2 108.55(12) . . ?
N1 C4 C3 112.57(12) . . ?
N2 C5 C6 109.78(12) . . ?
N3 C6 C5 110.09(12) . . ?

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
N1 H1N O3 0.907(15) 1.923(16) 2.8290(16) 177.2(19) 3_556
N1 H2N O8 0.920(16) 1.867(16) 2.7806(17) 172(2) 1_655
N1 H3N O9 0.913(15) 1.885(15) 2.7752(17) 164.4(17) 7_765
N2 H4N O6 0.890(15) 1.910(16) 2.7811(17) 165.6(18) 7_665
N2 H5N O2 0.902(16) 1.885(16) 2.7857(16) 177(2) .
N2 H6N O5 0.903(16) 1.848(17) 2.7420(17) 170(2) 1_455
N3 H7N O5 0.923(15) 1.811(16) 2.7260(16) 170.4(19) 6_556
N3 H8N O1 0.921(16) 1.770(16) 2.6634(16) 163(2) 4
N3 H9N O4 0.923(15) 2.215(18) 2.9473(17) 135.7(17) 7_665
O4 H4 O1 0.864(17) 1.638(18) 2.4919(15) 169(3) .
O7 H7 O3 0.849(16) 1.997(17) 2.8189(14) 163(2) 7_665
O8 H8A O2 0.847(16) 1.894(17) 2.7281(15) 168(2) .
O8 H8B O3 0.857(16) 1.918(17) 2.7331(15) 158(2) 7_665
O9 H9A O6 0.852(16) 1.926(16) 2.7767(15) 177(2) .
O9 H9B O2 0.856(16) 1.889(16) 2.7402(15) 172(2) 1_655

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1553749'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O7 P2, C8 H14 N2, 4(H2 O)'
_chemical_formula_sum            'C12 H33 N3 O11 P2'
_chemical_formula_weight         457.35

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      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                   6.8311(2)
_cell_length_b                   16.1499(6)
_cell_length_c                   18.8388(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.751(3)
_cell_angle_gamma                90
_cell_volume                     2059.34(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6984
_cell_measurement_theta_min      2.1777
_cell_measurement_theta_max      32.2927

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_T_min  0.95533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            25811
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         32.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6816
_reflns_number_gt                5981
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0384P)²+0.9411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6816
_refine_ls_number_parameters     311
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_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_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 0.23323(4) 0.03960(2) 0.14577(2) 0.00821(6) Uani 1 1 d . . . . .
P2 P 0.35015(4) 0.21839(2) 0.18748(2) 0.00912(6) Uani 1 1 d . . . . .
O1 O 0.25440(11) 0.03687(5) 0.22823(4) 0.01156(14) Uani 1 1 d . . . . .
O2 O 0.01785(11) 0.04904(5) 0.11356(4) 0.01242(15) Uani 1 1 d . . . . .
O3 O 0.33645(11) -0.03365(5) 0.11548(4) 0.01137(14) Uani 1 1 d . . . . .
O4 O 0.42002(12) 0.17686(5) 0.26293(4) 0.01388(15) Uani 1 1 d D . . . .
H4 H 0.364(2) 0.1302(9) 0.2603(9) 0.021 Uiso 1 1 d D U . . .
O5 O 0.13606(11) 0.24307(5) 0.18115(4) 0.01417(15) Uani 1 1 d . . . . .
O6 O 0.49429(12) 0.28699(5) 0.17768(4) 0.01373(15) Uani 1 1 d . . . . .
O7 O 0.58006(11) 0.11334(5) 0.13195(4) 0.01063(14) Uani 1 1 d D . . . .
H7 H 0.619(2) 0.1101(10) 0.0908(7) 0.016 Uiso 1 1 d D U . . .
O8 O 0.77900(12) 0.12372(5) 0.01066(4) 0.01475(16) Uani 1 1 d D . . . .
H8A H 0.873(2) 0.0983(10) 0.0377(8) 0.022 Uiso 1 1 d D U . . .
H8B H 0.753(3) 0.0971(13) -0.0288(9) 0.045(6) Uiso 1 1 d D . . . .
O9 O 0.03104(14) 0.38908(6) 0.23327(5) 0.01870(17) Uani 1 1 d D . . . .
H9A H -0.067(3) 0.3751(11) 0.2533(10) 0.028 Uiso 1 1 d D U . . .
H9B H 0.078(3) 0.3443(11) 0.2179(10) 0.028 Uiso 1 1 d D U . . .
O10 O -0.25690(14) 0.32872(6) 0.30812(5) 0.02135(18) Uani 1 1 d D . . . .
H10A H -0.352(2) 0.3177(12) 0.2760(9) 0.032 Uiso 1 1 d D U . . .
H10B H -0.298(3) 0.3701(10) 0.3311(9) 0.032 Uiso 1 1 d D U . . .
O11 O 0.57157(14) -0.03656(6) 0.31006(6) 0.0244(2) Uani 1 1 d D . . . .
H11A H 0.465(2) -0.0207(12) 0.2855(9) 0.037 Uiso 1 1 d D U . . .
H11B H 0.564(3) -0.0878(13) 0.3181(10) 0.037 Uiso 1 1 d D U . . .
N1 N 0.25983(14) 0.06960(6) -0.13924(5) 0.01098(16) Uani 1 1 d D . . . .
H1N H 0.216(2) 0.0870(10) -0.1841(7) 0.016 Uiso 1 1 d D U . . .
H2N H 0.3835(19) 0.0494(10) -0.1378(8) 0.016 Uiso 1 1 d D U . . .
H3N H 0.176(2) 0.0299(9) -0.1287(8) 0.016 Uiso 1 1 d D U . . .
N2 N -0.20459(14) 0.27357(6) 0.09412(5) 0.01264(17) Uani 1 1 d D . . . .
H4N H -0.086(2) 0.2628(10) 0.1191(8) 0.019 Uiso 1 1 d D U . . .
H5N H -0.226(2) 0.2369(9) 0.0583(8) 0.019 Uiso 1 1 d D U . . .
H6N H -0.297(2) 0.2670(10) 0.1234(8) 0.019 Uiso 1 1 d D U . . .
N3 N -0.13131(15) 0.42969(6) -0.23526(5) 0.01331(17) Uani 1 1 d D . . . .
H7N H -0.202(2) 0.4175(10) -0.2783(7) 0.020 Uiso 1 1 d D U . . .
H8N H -0.015(2) 0.4530(10) -0.2418(9) 0.020 Uiso 1 1 d D U . . .
H9N H -0.206(2) 0.4655(9) -0.2154(9) 0.020 Uiso 1 1 d D U . . .
C1 C 0.37074(14) 0.13425(6) 0.12292(5) 0.00855(17) Uani 1 1 d . . . . .
C2 C 0.30036(15) 0.16670(6) 0.04695(5) 0.00989(17) Uani 1 1 d . . . . .
H2A H 0.1667 0.1907 0.0461 0.012 Uiso 1 1 calc R U . . .
H2B H 0.3898 0.2117 0.0359 0.012 Uiso 1 1 calc R U . . .
C3 C 0.29330(15) 0.10073(6) -0.01161(5) 0.01045(18) Uani 1 1 d . . . . .
H3A H 0.4207 0.0707 -0.0064 0.013 Uiso 1 1 calc R U . . .
H3B H 0.1881 0.0602 -0.0055 0.013 Uiso 1 1 calc R U . . .
C4 C 0.25396(17) 0.13779(7) -0.08620(5) 0.01259(19) Uani 1 1 d . . . . .
H4A H 0.1229 0.1650 -0.0933 0.015 Uiso 1 1 calc R U . . .
H4B H 0.3556 0.1799 -0.0926 0.015 Uiso 1 1 calc R U . . .
C5 C -0.07977(17) 0.37461(7) 0.01096(6) 0.0143(2) Uani 1 1 d . . . . .
C6 C -0.14372(16) 0.35794(7) -0.06116(6) 0.01363(19) Uani 1 1 d . . . . .
H6 H -0.2727 0.3364 -0.0748 0.016 Uiso 1 1 calc R U . . .
C7 C -0.02140(16) 0.37236(7) -0.11354(6) 0.01287(19) Uani 1 1 d . . . . .
C8 C 0.16772(17) 0.40425(8) -0.09264(6) 0.0167(2) Uani 1 1 d . . . . .
H8 H 0.2528 0.4145 -0.1276 0.020 Uiso 1 1 calc R U . . .
C9 C 0.23209(18) 0.42102(8) -0.02087(7) 0.0193(2) Uani 1 1 d . . . . .
H9 H 0.3607 0.4429 -0.0072 0.023 Uiso 1 1 calc R U . . .
C10 C 0.10984(18) 0.40598(7) 0.03121(6) 0.0173(2) Uani 1 1 d . . . . .
H10 H 0.1553 0.4170 0.0802 0.021 Uiso 1 1 calc R U . . .
C11 C -0.21672(18) 0.36016(7) 0.06617(6) 0.0169(2) Uani 1 1 d . . . . .
H11C H -0.1827 0.3991 0.1065 0.020 Uiso 1 1 calc R U . . .
H11D H -0.3542 0.3718 0.0445 0.020 Uiso 1 1 calc R U . . .
C12 C -0.09591(17) 0.35286(7) -0.19059(6) 0.0141(2) Uani 1 1 d . . . . .
H12A H 0.0019 0.3176 -0.2106 0.017 Uiso 1 1 calc R U . . .
H12B H -0.2207 0.3212 -0.1930 0.017 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 O2 1.5216(8) . ?
P1 O3 1.5267(8) . ?
P1 O1 1.5413(8) . ?
P1 C1 1.8743(10) . ?
P2 O5 1.5049(8) . ?
P2 O6 1.5100(8) . ?
P2 O4 1.5859(8) . ?
P2 C1 1.8417(10) . ?
O7 C1 1.4567(12) . ?
N1 C4 1.4912(13) . ?
N2 C11 1.4926(15) . ?
N3 C12 1.5004(14) . ?
C1 C2 1.5388(14) . ?
C2 C3 1.5297(14) . ?
C3 C4 1.5177(14) . ?
C5 C10 1.3952(16) . ?
C5 C6 1.3960(15) . ?
C5 C11 1.5080(16) . ?
C6 C7 1.3960(15) . ?
C7 C8 1.3973(16) . ?
C7 C12 1.5052(15) . ?
C8 C9 1.3908(16) . ?
C9 C10 1.3927(17) . ?

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 P1 O3 113.52(4) . . ?
O2 P1 O1 111.04(4) . . ?
O3 P1 O1 111.67(4) . . ?
O2 P1 C1 108.32(4) . . ?
O3 P1 C1 105.97(4) . . ?
O1 P1 C1 105.85(4) . . ?
O5 P2 O6 116.03(5) . . ?
O5 P2 O4 110.78(5) . . ?
O6 P2 O4 107.31(5) . . ?
O5 P2 C1 107.64(4) . . ?
O6 P2 C1 110.58(5) . . ?
O4 P2 C1 103.84(4) . . ?
O7 C1 C2 111.48(8) . . ?
O7 C1 P2 104.78(6) . . ?
C2 C1 P2 108.71(7) . . ?
O7 C1 P1 107.37(6) . . ?
C2 C1 P1 112.82(7) . . ?
P2 C1 P1 111.39(5) . . ?
C3 C2 C1 114.15(8) . . ?
C4 C3 C2 112.18(8) . . ?
N1 C4 C3 108.16(8) . . ?
C10 C5 C6 119.55(10) . . ?
C10 C5 C11 120.46(10) . . ?
C6 C5 C11 119.97(10) . . ?
C5 C6 C7 121.15(10) . . ?
C6 C7 C8 118.75(10) . . ?
C6 C7 C12 119.35(10) . . ?
C8 C7 C12 121.90(10) . . ?
C9 C8 C7 120.32(11) . . ?
C8 C9 C10 120.65(11) . . ?
C9 C10 C5 119.57(10) . . ?
N2 C11 C5 112.22(9) . . ?
N3 C12 C7 112.07(9) . . ?

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
N1 H1N O9 0.903(13) 1.906(13) 2.7648(12) 158.2(14) 4_565
N1 H2N O3 0.902(13) 1.920(13) 2.7946(12) 162.9(15) 3_655
N1 H3N O2 0.902(13) 1.885(13) 2.7840(12) 174.6(15) 3
N2 H4N O5 0.899(13) 1.812(13) 2.7050(12) 171.6(15) .
N2 H5N O8 0.894(13) 2.039(14) 2.8799(13) 156.2(15) 1_455
N2 H6N O6 0.896(13) 1.894(13) 2.7623(12) 162.7(15) 1_455
N3 H7N O7 0.906(13) 2.157(13) 3.0493(12) 168.0(14) 4_465
N3 H8N O1 0.899(13) 2.007(14) 2.8628(13) 158.6(15) 4_565
N3 H9N O11 0.889(13) 2.010(14) 2.8801(14) 165.7(15) 4_465
O4 H4 O1 0.843(13) 1.754(14) 2.5728(11) 163.2(17) .
O7 H7 O8 0.856(13) 1.990(13) 2.8168(11) 162.1(15) .
O8 H8A O2 0.868(13) 1.809(14) 2.6499(11) 162.6(16) 1_655
O8 H8B O3 0.856(15) 1.955(15) 2.8070(11) 173.5(19) 3_655
O9 H9A O10 0.844(17) 1.915(17) 2.7487(14) 169.3(18) .
O9 H9B O5 0.855(17) 1.841(17) 2.6887(12) 170.8(18) .
O10 H10A O6 0.843(14) 2.064(15) 2.8730(12) 160.7(17) 1_455
O10 H10B O3 0.863(14) 1.889(14) 2.7420(12) 169.2(18) 2
O11 H11A O1 0.848(12) 1.918(12) 2.7525(12) 167.7(19) .
O11 H11B O6 0.84(2) 2.07(2) 2.8989(13) 169.5(18) 2_645

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.321
_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_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1553750'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C4 H11 N O7 P2), 2(C8 H22 N2), 4(H2 O), C2 H6 O'
_chemical_formula_sum            'C26 H80 N6 O19 P4'
_chemical_formula_weight         904.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   43.2210(13)
_cell_length_b                   8.4871(2)
_cell_length_c                   11.9087(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.289(3)
_cell_angle_gamma                90
_cell_volume                     4322.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7222
_cell_measurement_theta_min      3.7478
_cell_measurement_theta_max      66.7731

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             1960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.288
_shelx_estimated_absorpt_T_min   0.658
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_T_min  0.72644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            21897
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.134
_diffrn_reflns_theta_max         66.879
_diffrn_reflns_theta_full        66.879
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3831
_reflns_number_gt                3345
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0474P)²+4.5211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3831
_refine_ls_number_parameters     375
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.044
_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_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 0.13977(2) 0.19377(5) 0.25727(4) 0.01230(12) Uani 1 1 d . . . . .
P2 P 0.16848(2) 0.51829(5) 0.32419(4) 0.01145(12) Uani 1 1 d . . . . .
O1 O 0.10900(3) 0.28950(14) 0.26911(11) 0.0176(3) Uani 1 1 d D . . . .
O2 O 0.15301(3) 0.11788(14) 0.36918(10) 0.0156(3) Uani 1 1 d . . . . .
O3 O 0.13224(3) 0.08130(14) 0.15957(10) 0.0174(3) Uani 1 1 d . . . . .
O4 O 0.13444(3) 0.54931(14) 0.33997(10) 0.0157(3) Uani 1 1 d . . . . .
O5 O 0.18888(3) 0.47736(14) 0.43565(10) 0.0154(3) Uani 1 1 d . . . . .
O6 O 0.18187(3) 0.65409(14) 0.26224(10) 0.0156(3) Uani 1 1 d . . . . .
O7 O 0.15367(3) 0.40291(14) 0.11287(10) 0.0144(3) Uani 1 1 d D . . . .
O8 O 0.20570(3) 0.92839(15) 0.35604(11) 0.0185(3) Uani 1 1 d D . . . .
O9 O 0.21761(3) 0.72074(16) 0.09526(12) 0.0217(3) Uani 1 1 d D . . . .
O10 O 0.04588(9) 0.1806(5) 0.2359(4) 0.0534(10) Uani 0.5 1 d D . P A -1
N1 N 0.24563(3) 0.00555(17) 0.05650(13) 0.0146(3) Uani 1 1 d D . . . .
N2 N 0.13854(3) 0.77568(18) 0.08322(13) 0.0152(3) Uani 1 1 d D . . . .
N3 N -0.12280(3) 0.83523(18) 0.06836(14) 0.0157(3) Uani 1 1 d D . . . .
C1 C 0.16733(4) 0.34780(19) 0.22417(14) 0.0121(3) Uani 1 1 d . . . . .
C2 C 0.20079(4) 0.28726(19) 0.22468(15) 0.0133(3) Uani 1 1 d . . . . .
H2A H 0.2144 0.3784 0.2148 0.016 Uiso 1 1 calc R U . . .
H2B H 0.2081 0.2408 0.3001 0.016 Uiso 1 1 calc R U . . .
C3 C 0.20496(4) 0.1644(2) 0.13376(15) 0.0144(4) Uani 1 1 d . . . . .
H3A H 0.1927 0.0686 0.1453 0.017 Uiso 1 1 calc R U . . .
H3B H 0.1973 0.2072 0.0574 0.017 Uiso 1 1 calc R U . . .
C4 C 0.23932(4) 0.1241(2) 0.14286(15) 0.0163(4) Uani 1 1 d . . . . .
H4A H 0.2513 0.2213 0.1329 0.020 Uiso 1 1 calc R U . . .
H4B H 0.2467 0.0822 0.2197 0.020 Uiso 1 1 calc R U . . .
C5 C 0.1074(2) 0.7026(16) 0.0480(12) 0.0190(19) Uani 0.503(4) 1 d D . P B 1
H5A H 0.1099 0.5866 0.0465 0.023 Uiso 0.503(4) 1 calc R U P B 1
H5B H 0.0992 0.7376 -0.0300 0.023 Uiso 0.503(4) 1 calc R U P B 1
C5' C 0.1087(2) 0.6820(16) 0.0717(12) 0.0190(19) Uani 0.497(4) 1 d D . P B 2
H5'1 H 0.1071 0.6288 0.1446 0.023 Uiso 0.497(4) 1 calc R U P B 2
H5'2 H 0.1093 0.5995 0.0133 0.023 Uiso 0.497(4) 1 calc R U P B 2
C6 C 0.08415(8) 0.7440(5) 0.1255(3) 0.0202(9) Uani 0.503(4) 1 d D . P B 1
H6A H 0.0851 0.8584 0.1416 0.024 Uiso 0.503(4) 1 calc R U P B 1
H6B H 0.0894 0.6870 0.1983 0.024 Uiso 0.503(4) 1 calc R U P B 1
C6' C 0.08008(8) 0.7834(4) 0.0392(4) 0.0203(9) Uani 0.497(4) 1 d D . P B 2
H6'1 H 0.0798 0.8214 -0.0396 0.024 Uiso 0.497(4) 1 calc R U P B 2
H6'2 H 0.0815 0.8767 0.0895 0.024 Uiso 0.497(4) 1 calc R U P B 2
C7 C 0.0514(2) 0.700(2) 0.0710(15) 0.027(2) Uani 0.503(4) 1 d D . P B 1
H7A H 0.0503 0.5840 0.0613 0.032 Uiso 0.503(4) 1 calc R U P B 1
H7B H 0.0474 0.7478 -0.0056 0.032 Uiso 0.503(4) 1 calc R U P B 1
C7' C 0.0496(2) 0.6970(19) 0.0472(16) 0.027(2) Uani 0.497(4) 1 d D . P B 2
H7'1 H 0.0461 0.6170 -0.0139 0.032 Uiso 0.497(4) 1 calc R U P B 2
H7'2 H 0.0515 0.6409 0.1207 0.032 Uiso 0.497(4) 1 calc R U P B 2
C8 C 0.02560(9) 0.7512(5) 0.1376(4) 0.0270(10) Uani 0.503(4) 1 d D . P B 1
H8A H 0.0286 0.8639 0.1578 0.032 Uiso 0.503(4) 1 calc R U P B 1
H8B H 0.0275 0.6903 0.2092 0.032 Uiso 0.503(4) 1 calc R U P B 1
C8' C 0.02162(9) 0.8053(5) 0.0373(4) 0.0269(10) Uani 0.497(4) 1 d D . P B 2
H8'1 H 0.0204 0.8646 -0.0348 0.032 Uiso 0.497(4) 1 calc R U P B 2
H8'2 H 0.0249 0.8827 0.1000 0.032 Uiso 0.497(4) 1 calc R U P B 2
C9 C -0.0073(2) 0.728(2) 0.0730(12) 0.034(2) Uani 0.503(4) 1 d D . P B 1
H9A H -0.0091 0.7864 0.0002 0.040 Uiso 0.503(4) 1 calc R U P B 1
H9B H -0.0107 0.6152 0.0554 0.040 Uiso 0.503(4) 1 calc R U P B 1
C9' C -0.0095(2) 0.722(2) 0.0404(12) 0.034(2) Uani 0.497(4) 1 d D . P B 2
H9'1 H -0.0146 0.6568 -0.0285 0.040 Uiso 0.497(4) 1 calc R U P B 2
H9'2 H -0.0077 0.6519 0.1072 0.040 Uiso 0.497(4) 1 calc R U P B 2
C10 C -0.03281(9) 0.7857(5) 0.1393(4) 0.0255(10) Uani 0.503(4) 1 d D . P B 1
H10A H -0.0280 0.8949 0.1656 0.031 Uiso 0.503(4) 1 calc R U P B 1
H10B H -0.0329 0.7184 0.2071 0.031 Uiso 0.503(4) 1 calc R U P B 1
C10' C -0.03588(9) 0.8393(5) 0.0466(4) 0.0256(10) Uani 0.497(4) 1 d D . P B 2
H10C H -0.0379 0.9088 -0.0209 0.031 Uiso 0.497(4) 1 calc R U P B 2
H10D H -0.0306 0.9062 0.1148 0.031 Uiso 0.497(4) 1 calc R U P B 2
C11 C -0.06608(18) 0.782(2) 0.066(2) 0.0258(19) Uani 0.503(4) 1 d D . P B 1
H11A H -0.0626 0.7891 -0.0143 0.031 Uiso 0.503(4) 1 calc R U P B 1
H11B H -0.0747 0.6753 0.0758 0.031 Uiso 0.503(4) 1 calc R U P B 1
C11' C -0.06803(19) 0.754(2) 0.052(2) 0.0258(19) Uani 0.497(4) 1 d D . P B 2
H11C H -0.0641 0.6460 0.0820 0.031 Uiso 0.497(4) 1 calc R U P B 2
H11D H -0.0798 0.7454 -0.0256 0.031 Uiso 0.497(4) 1 calc R U P B 2
C12 C -0.09047(10) 0.8906(5) 0.0791(5) 0.0182(9) Uani 0.503(4) 1 d . . P B 1
H12A H -0.0897 0.9756 0.0226 0.022 Uiso 0.503(4) 1 calc R U P B 1
H12B H -0.0853 0.9394 0.1550 0.022 Uiso 0.503(4) 1 calc R U P B 1
C12' C -0.08935(9) 0.8518(5) 0.1339(4) 0.0169(9) Uani 0.497(4) 1 d . . P B 2
H12C H -0.0877 0.8037 0.2102 0.020 Uiso 0.497(4) 1 calc R U P B 2
H12D H -0.0829 0.9637 0.1416 0.020 Uiso 0.497(4) 1 calc R U P B 2
C13 C 0.02752(16) 0.3164(8) 0.2343(6) 0.0636(16) Uani 0.5 1 d D U P A -1
H13A H 0.0296 0.3802 0.1663 0.076 Uiso 0.5 1 calc R U P A -1
H13B H 0.0344 0.3810 0.3025 0.076 Uiso 0.5 1 calc R U P A -1
H1 H 0.1146(7) 0.381(3) 0.298(2) 0.059(9) Uiso 1 1 d D . . . .
H1N H 0.2666(4) -0.004(3) 0.055(2) 0.032(6) Uiso 1 1 d D . . . .
H2N H 0.2373(5) -0.088(2) 0.0728(19) 0.025(6) Uiso 1 1 d D . . . .
H3N H 0.2360(5) 0.034(3) -0.0146(15) 0.032(6) Uiso 1 1 d D . . . .
H4N H 0.1360(5) 0.873(2) 0.1125(18) 0.023(6) Uiso 1 1 d D . . . .
H5N H 0.1464(5) 0.791(3) 0.0190(16) 0.023(6) Uiso 1 1 d D . . . .
H6N H 0.1519(5) 0.722(3) 0.1340(18) 0.029(6) Uiso 1 1 d D . . . .
H7 H 0.1677(5) 0.438(3) 0.0742(19) 0.031(6) Uiso 1 1 d D . . . .
H8C H 0.1979(6) 0.841(2) 0.328(2) 0.046(8) Uiso 1 1 d D . . . .
H8D H 0.1902(4) 0.990(2) 0.3599(19) 0.025(6) Uiso 1 1 d D . . . .
H8N H -0.1354(5) 0.906(2) 0.0963(19) 0.029(6) Uiso 1 1 d D . . . .
H9C H 0.2085(6) 0.698(3) 0.1533(16) 0.037(7) Uiso 1 1 d D . . . .
H9D H 0.2067(5) 0.671(3) 0.0433(17) 0.035(7) Uiso 1 1 d D . . . .
H9N H -0.1288(5) 0.741(2) 0.094(2) 0.034(6) Uiso 1 1 d D . . . .
H7N H -0.1268(6) 0.835(3) -0.0082(15) 0.041(7) Uiso 1 1 d D . . . .
C14 C -0.0057(3) 0.2669(11) 0.2323(13) 0.099(4) Uani 0.5 1 d D U P A -1
H14A H -0.0190 0.3605 0.2311 0.148 Uiso 0.5 1 calc R U P A -1
H14B H -0.0124 0.2034 0.1643 0.148 Uiso 0.5 1 calc R U P A -1
H14C H -0.0076 0.2042 0.3001 0.148 Uiso 0.5 1 calc R U P A -1
H10 H 0.0649(8) 0.221(9) 0.248(7) 0.09(2) Uiso 0.5 1 d D . P C -1


_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 O3 1.5038(13) . ?
P1 O2 1.5161(12) . ?
P1 O1 1.5820(12) . ?
P1 C1 1.8489(17) . ?
P2 O5 1.5241(13) . ?
P2 O6 1.5266(12) . ?
P2 O4 1.5325(12) . ?
P2 C1 1.8702(17) . ?
O7 C1 1.449(2) . ?
O10 C13 1.398(8) . ?
N1 C4 1.492(2) . ?
N2 C5 1.486(10) . ?
N2 C5' 1.506(10) . ?
N3 C12 1.462(4) . ?
N3 C12' 1.547(4) . ?
C1 C2 1.534(2) . ?
C2 C3 1.532(2) . ?
C3 C4 1.513(2) . ?
C5 C6 1.501(12) . ?
C5' C6' 1.510(11) . ?
C6 C7 1.517(11) . ?
C6' C7' 1.524(12) . ?
C7 C8 1.522(11) . ?
C7' C8' 1.509(13) . ?
C8 C9 1.530(10) . ?
C8' C9' 1.525(12) . ?
C9 C10 1.524(10) . ?
C9' C10' 1.519(12) . ?
C10 C11 1.572(13) . ?
C10' C11' 1.577(13) . ?
C11 C12 1.427(13) . ?
C11' C12' 1.658(16) . ?
C13 C14 1.494(12) . ?

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 O2 115.00(7) . . ?
O3 P1 O1 107.70(7) . . ?
O2 P1 O1 110.82(7) . . ?
O3 P1 C1 110.98(7) . . ?
O2 P1 C1 108.34(7) . . ?
O1 P1 C1 103.39(7) . . ?
O5 P2 O6 112.39(7) . . ?
O5 P2 O4 112.18(7) . . ?
O6 P2 O4 111.54(7) . . ?
O5 P2 C1 109.71(7) . . ?
O6 P2 C1 104.68(7) . . ?
O4 P2 C1 105.85(7) . . ?
O7 C1 C2 111.80(13) . . ?
O7 C1 P1 103.50(10) . . ?
C2 C1 P1 113.47(11) . . ?
O7 C1 P2 107.63(11) . . ?
C2 C1 P2 108.55(11) . . ?
P1 C1 P2 111.72(9) . . ?
C3 C2 C1 115.58(14) . . ?
C4 C3 C2 108.50(14) . . ?
N1 C4 C3 112.24(14) . . ?
N2 C5 C6 112.8(9) . . ?
N2 C5' C6' 112.4(8) . . ?
C5 C6 C7 110.2(7) . . ?
C5' C6' C7' 113.1(8) . . ?
C6 C7 C8 114.5(9) . . ?
C8' C7' C6' 113.1(11) . . ?
C7 C8 C9 113.6(7) . . ?
C7' C8' C9' 114.7(8) . . ?
C10 C9 C8 112.9(8) . . ?
C10' C9' C8' 111.8(11) . . ?
C9 C10 C11 112.1(8) . . ?
C9' C10' C11' 111.9(9) . . ?
C12 C11 C10 123.8(11) . . ?
C10' C11' C12' 111.2(9) . . ?
C11 C12 N3 119.6(7) . . ?
N3 C12' C11' 102.5(5) . . ?
O10 C13 C14 108.1(6) . . ?

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
O1 H1 O4 0.866(18) 1.707(19) 2.5525(17) 165(3) .
N1 H1N O5 0.910(16) 1.920(17) 2.8286(19) 176(2) 4_545
N1 H2N O9 0.907(16) 1.867(17) 2.772(2) 175(2) 1_545
N1 H3N O8 0.921(16) 1.899(17) 2.794(2) 163(2) 6_565
N2 H4N O3 0.908(16) 1.870(17) 2.7749(19) 174(2) 1_565
N2 H5N O2 0.890(16) 2.003(17) 2.857(2) 161(2) 6_565
N2 H6N O6 0.898(16) 1.942(17) 2.822(2) 166(2) .
O7 H7 O5 0.866(16) 2.124(18) 2.9545(17) 161(2) 6_565
O8 H8C O6 0.864(17) 1.856(17) 2.7196(17) 177(3) .
O8 H8D O2 0.857(16) 1.955(16) 2.8106(18) 176(2) 1_565
N3 H8N O2 0.903(16) 2.021(18) 2.8798(19) 158(2) 2_565
O9 H9C O6 0.866(16) 1.891(17) 2.7471(18) 170(2) .
O9 H9D O5 0.837(16) 1.879(17) 2.7021(18) 167(3) 6_565
N3 H9N O4 0.909(17) 1.837(17) 2.7372(19) 170(2) 2
N3 H7N O3 0.904(17) 1.921(19) 2.778(2) 158(2) 5_565
N3 H7N O7 0.904(17) 2.56(2) 3.1134(19) 120(2) 5_565
O10 H10 O1 0.88(2) 1.98(2) 2.854(4) 173(7) .

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1553751'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O7 P2, 2(C8 H12 N), 2(H2 O)'
_chemical_formula_sum            'C20 H39 N3 O9 P2'
_chemical_formula_weight         527.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.5015(3)
_cell_length_b                   11.7989(4)
_cell_length_c                   25.7287(10)
_cell_angle_alpha                77.382(3)
_cell_angle_beta                 85.424(3)
_cell_angle_gamma                90.021(3)
_cell_volume                     2510.02(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      5.2960
_cell_measurement_theta_max      66.4960

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.046
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.79945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            20488
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.533
_diffrn_reflns_theta_max         66.699
_diffrn_reflns_theta_full        66.699
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             20488
_reflns_number_gt                16187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 1.171.38.43d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 4-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1628P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         20488
_refine_ls_number_parameters     706
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.2259
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.2942 5892 21829 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3161 6515 22104 nmt -0.7702 -0.4593 -0.0001 0.8853 -0.7703 0.0000 -0.0114
-0.9552 0.9998
3 0.2373 6273 22311 nmt -0.7703 0.4592 0.0001 0.8855 0.7707 -0.0001 0.4820
0.9562 -1.0005
4 0.1524 5915 21775 nmt 0.9997 0.0002 -0.0000 0.0004 -1.0003 -0.0001 0.4941
-0.0007 -1.0008

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 0.39804(16) 0.09725(11) 0.18667(5) 0.0110(3) Uani 1 1 d . . . . .
P2 P 0.73523(15) 0.06823(10) 0.13971(5) 0.0107(3) Uani 1 1 d . . . . .
P3 P 1.01259(16) 0.59702(10) 0.18687(5) 0.0111(3) Uani 1 1 d . . . . .
P4 P 0.69732(15) 0.56757(10) 0.14019(5) 0.0105(3) Uani 1 1 d . . . . .
O1 O 0.4781(4) 0.0452(3) 0.24006(13) 0.0148(7) Uani 1 1 d D . . . .
H1C H 0.559(6) 0.007(5) 0.234(3) 0.022 Uiso 1 1 d D U . . .
O2 O 0.2822(5) 0.1860(3) 0.19826(13) 0.0152(8) Uani 1 1 d . . . . .
O3 O 0.3309(4) 0.0015(3) 0.16401(13) 0.0145(7) Uani 1 1 d . . . . .
O4 O 0.7522(4) 0.0094(3) 0.19817(13) 0.0154(8) Uani 1 1 d . . . . .
O5 O 0.8772(4) 0.1476(3) 0.11641(14) 0.0158(8) Uani 1 1 d . . . . .
O6 O 0.7020(4) -0.0184(3) 0.10562(13) 0.0137(7) Uani 1 1 d . . . . .
O7 O 0.6122(5) 0.2611(3) 0.16450(13) 0.0137(7) Uani 1 1 d D . . . .
H7C H 0.651(8) 0.315(5) 0.139(2) 0.021 Uiso 1 1 d D U . . .
O8 O 0.9071(5) 0.5458(3) 0.24039(13) 0.0157(8) Uani 1 1 d D . . . .
H8C H 0.809(4) 0.537(6) 0.236(3) 0.024 Uiso 1 1 d D U . . .
O9 O 1.1246(5) 0.6855(3) 0.19809(14) 0.0159(8) Uani 1 1 d . . . . .
O10 O 1.0916(4) 0.5011(3) 0.16435(13) 0.0136(7) Uani 1 1 d . . . . .
O11 O 0.6543(4) 0.5079(3) 0.19840(14) 0.0166(8) Uani 1 1 d . . . . .
O12 O 0.5663(4) 0.6477(3) 0.11726(14) 0.0152(8) Uani 1 1 d . . . . .
O13 O 0.7459(4) 0.4815(3) 0.10557(13) 0.0141(7) Uani 1 1 d . . . . .
O14 O 0.8091(5) 0.7606(3) 0.16471(14) 0.0144(7) Uani 1 1 d D . . . .
H14C H 0.779(8) 0.813(5) 0.140(2) 0.022 Uiso 1 1 d D U . . .
O15 O 0.1621(5) 0.0882(3) 0.07491(14) 0.0180(8) Uani 1 1 d D . . . .
H15C H 0.068(4) 0.099(6) 0.089(2) 0.027 Uiso 1 1 d D U . . .
H15D H 0.211(7) 0.054(6) 0.1021(19) 0.027 Uiso 1 1 d D U . . .
O16 O 0.9615(5) 0.3633(3) 0.05601(16) 0.0215(8) Uani 1 1 d D . . . .
H16C H 0.922(9) 0.413(4) 0.076(2) 0.032 Uiso 1 1 d D U . . .
H16D H 0.929(9) 0.295(3) 0.077(3) 0.032 Uiso 1 1 d D U . . .
O17 O 0.5125(5) 0.8625(4) 0.05625(16) 0.0205(8) Uani 1 1 d D . . . .
H17C H 0.526(10) 0.792(4) 0.066(3) 0.031 Uiso 1 1 d D U . . .
H17D H 0.548(9) 0.897(5) 0.077(3) 0.031 Uiso 1 1 d D U . . .
O18 O 0.3018(5) 0.5874(3) 0.07531(14) 0.0175(8) Uani 1 1 d D . . . .
H18C H 0.387(5) 0.613(6) 0.086(2) 0.026 Uiso 1 1 d D U . . .
H18D H 0.251(7) 0.559(6) 0.1049(17) 0.026 Uiso 1 1 d D U . . .
N1 N 0.2541(6) 0.4402(4) 0.00641(16) 0.0128(9) Uani 1 1 d D . . . .
H1N H 0.285(8) 0.500(4) 0.020(2) 0.019 Uiso 1 1 d D U . . .
H2N H 0.239(8) 0.467(6) -0.0285(13) 0.019 Uiso 1 1 d D U . . .
H3N H 0.159(5) 0.412(5) 0.022(2) 0.019 Uiso 1 1 d D U . . .
N2 N 1.2420(6) 0.9397(4) 0.00659(16) 0.0139(9) Uani 1 1 d D . . . .
H4N H 1.217(8) 0.997(4) 0.025(2) 0.021 Uiso 1 1 d D U . . .
H5N H 1.332(5) 0.915(6) 0.022(2) 0.021 Uiso 1 1 d D U . . .
H6N H 1.253(8) 0.972(5) -0.0290(13) 0.021 Uiso 1 1 d D U . . .
N3 N 0.0339(5) -0.0986(4) 0.21498(17) 0.0142(9) Uani 1 1 d D . . . .
H7N H 0.115(6) -0.052(5) 0.196(2) 0.021 Uiso 1 1 d D U . . .
H8N H 0.021(8) -0.159(4) 0.199(2) 0.021 Uiso 1 1 d D U . . .
H9N H -0.049(6) -0.050(5) 0.209(2) 0.021 Uiso 1 1 d D U . . .
N4 N 0.9788(6) 0.2682(4) 0.19160(17) 0.0146(9) Uani 1 1 d D . . . .
H10N H 0.995(8) 0.343(3) 0.174(2) 0.022 Uiso 1 1 d D U . . .
H11N H 0.936(8) 0.217(5) 0.174(2) 0.022 Uiso 1 1 d D U . . .
H12N H 1.075(5) 0.236(6) 0.196(3) 0.022 Uiso 1 1 d D U . . .
N5 N 0.3633(5) 0.4013(4) 0.21588(17) 0.0134(9) Uani 1 1 d D . . . .
H13N H 0.285(6) 0.439(5) 0.197(2) 0.020 Uiso 1 1 d D U . . .
H14N H 0.375(8) 0.336(4) 0.203(2) 0.020 Uiso 1 1 d D U . . .
H15N H 0.458(5) 0.440(5) 0.210(2) 0.020 Uiso 1 1 d D U . . .
N6 N 0.4301(6) 0.7688(4) 0.19246(17) 0.0151(9) Uani 1 1 d D . . . .
H16N H 0.415(9) 0.843(3) 0.175(2) 0.023 Uiso 1 1 d D U . . .
H17N H 0.492(7) 0.731(5) 0.171(2) 0.023 Uiso 1 1 d D U . . .
H18N H 0.334(5) 0.734(6) 0.196(3) 0.023 Uiso 1 1 d D U . . .
C1 C 0.5642(6) 0.1677(4) 0.14038(19) 0.0116(10) Uani 1 1 d . . . . .
C2 C 0.5204(6) 0.2120(4) 0.08330(19) 0.0129(10) Uani 1 1 d . . . . .
H2A H 0.4777 0.1460 0.0705 0.016 Uiso 1 1 calc R U . . .
H2B H 0.6179 0.2402 0.0604 0.016 Uiso 1 1 calc R U . . .
C3 C 0.3998(7) 0.3097(5) 0.0758(2) 0.0134(10) Uani 1 1 d . . . . .
H3A H 0.2996 0.2824 0.0972 0.016 Uiso 1 1 calc R U . . .
H3B H 0.4404 0.3772 0.0881 0.016 Uiso 1 1 calc R U . . .
C4 C 0.3716(7) 0.3449(4) 0.01704(19) 0.0157(10) Uani 1 1 d . . . . .
H4A H 0.4727 0.3713 -0.0040 0.019 Uiso 1 1 calc R U . . .
H4B H 0.3327 0.2765 0.0051 0.019 Uiso 1 1 calc R U . . .
C5 C 0.8677(6) 0.6672(4) 0.14068(19) 0.0118(10) Uani 1 1 d . . . . .
C6 C 0.9395(6) 0.7116(4) 0.08358(19) 0.0136(10) Uani 1 1 d . . . . .
H6A H 0.8531 0.7394 0.0607 0.016 Uiso 1 1 calc R U . . .
H6B H 0.9886 0.6454 0.0709 0.016 Uiso 1 1 calc R U . . .
C7 C 1.0639(7) 0.8097(5) 0.0756(2) 0.0148(11) Uani 1 1 d . . . . .
H7A H 1.0175 0.8772 0.0879 0.018 Uiso 1 1 calc R U . . .
H7B H 1.1542 0.7827 0.0969 0.018 Uiso 1 1 calc R U . . .
C8 C 1.1196(7) 0.8446(4) 0.0175(2) 0.0161(11) Uani 1 1 d . . . . .
H8A H 1.1641 0.7762 0.0055 0.019 Uiso 1 1 calc R U . . .
H8B H 1.0284 0.8709 -0.0034 0.019 Uiso 1 1 calc R U . . .
C9 C 0.0616(7) -0.1387(5) 0.2721(2) 0.0166(11) Uani 1 1 d . . . . .
H9A H 0.0771 -0.0704 0.2878 0.020 Uiso 1 1 calc R U . . .
H9B H 0.1592 -0.1846 0.2751 0.020 Uiso 1 1 calc R U . . .
C10 C -0.0752(7) -0.2124(5) 0.3031(2) 0.0213(12) Uani 1 1 d . . . . .
H10A H -0.1661 -0.1624 0.3082 0.026 Uiso 1 1 calc R U . . .
H10B H -0.1082 -0.2695 0.2829 0.026 Uiso 1 1 calc R U . . .
C11 C -0.0257(8) -0.2754(6) 0.3570(3) 0.0225(14) Uani 1 1 d . . . . .
C12 C 0.0300(10) -0.3882(6) 0.3640(3) 0.0321(17) Uani 1 1 d . . . . .
H12 H 0.0292 -0.4281 0.3357 0.038 Uiso 1 1 calc R U . . .
C13 C 0.0859(12) -0.4419(8) 0.4115(4) 0.043(2) Uani 1 1 d . . . . .
H13 H 0.1215 -0.5195 0.4160 0.051 Uiso 1 1 calc R U . . .
C14 C 0.0913(11) -0.3853(9) 0.4528(3) 0.044(2) Uani 1 1 d . . . . .
H14 H 0.1337 -0.4226 0.4851 0.053 Uiso 1 1 calc R U . . .
C15 C 0.0350(10) -0.2749(7) 0.4470(3) 0.0382(17) Uani 1 1 d . . . . .
H15 H 0.0354 -0.2364 0.4758 0.046 Uiso 1 1 calc R U . . .
C16 C -0.0224(8) -0.2190(6) 0.3994(3) 0.0269(14) Uani 1 1 d . . . . .
H16 H -0.0597 -0.1420 0.3955 0.032 Uiso 1 1 calc R U . . .
C17 C 0.8897(7) 0.2652(5) 0.24479(19) 0.0168(11) Uani 1 1 d . . . . .
H17A H 0.7757 0.2745 0.2399 0.020 Uiso 1 1 calc R U . . .
H17B H 0.9256 0.3311 0.2593 0.020 Uiso 1 1 calc R U . . .
C18 C 0.9141(7) 0.1518(5) 0.2846(2) 0.0194(11) Uani 1 1 d . . . . .
H18A H 0.8653 0.0869 0.2725 0.023 Uiso 1 1 calc R U . . .
H18B H 1.0286 0.1373 0.2860 0.023 Uiso 1 1 calc R U . . .
C19 C 0.8424(7) 0.1556(5) 0.3398(2) 0.0218(12) Uani 1 1 d . . . . .
C20 C 0.7300(9) 0.0752(7) 0.3662(3) 0.0315(16) Uani 1 1 d . . . . .
H20 H 0.6955 0.0170 0.3491 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6653(11) 0.0772(9) 0.4176(3) 0.046(2) Uani 1 1 d . . . . .
H21 H 0.5876 0.0210 0.4352 0.055 Uiso 1 1 calc R U . . .
C22 C 0.7151(10) 0.1614(9) 0.4426(3) 0.047(2) Uani 1 1 d . . . . .
H22 H 0.6720 0.1634 0.4776 0.056 Uiso 1 1 calc R U . . .
C23 C 0.8273(12) 0.2424(8) 0.4167(3) 0.045(2) Uani 1 1 d . . . . .
H23 H 0.8619 0.3002 0.4340 0.054 Uiso 1 1 calc R U . . .
C24 C 0.8905(10) 0.2406(7) 0.3655(3) 0.0344(18) Uani 1 1 d . . . . .
H24 H 0.9671 0.2976 0.3479 0.041 Uiso 1 1 calc R U . . .
C25 C 0.3058(7) 0.3602(5) 0.2731(2) 0.0194(11) Uani 1 1 d . . . . .
H25A H 0.2064 0.3148 0.2756 0.023 Uiso 1 1 calc R U . . .
H25B H 0.2832 0.4280 0.2891 0.023 Uiso 1 1 calc R U . . .
C26 C 0.4278(7) 0.2847(5) 0.3040(2) 0.0224(12) Uani 1 1 d . . . . .
H26A H 0.4709 0.2287 0.2832 0.027 Uiso 1 1 calc R U . . .
H26B H 0.5161 0.3341 0.3097 0.027 Uiso 1 1 calc R U . . .
C27 C 0.3519(8) 0.2196(6) 0.3574(3) 0.0235(14) Uani 1 1 d . . . . .
C28 C 0.2962(9) 0.1064(6) 0.3629(3) 0.0296(15) Uani 1 1 d . . . . .
H28 H 0.3079 0.0699 0.3333 0.036 Uiso 1 1 calc R U . . .
C29 C 0.2233(11) 0.0463(7) 0.4116(3) 0.042(2) Uani 1 1 d . . . . .
H29 H 0.1854 -0.0310 0.4151 0.050 Uiso 1 1 calc R U . . .
C30 C 0.2059(10) 0.0983(8) 0.4546(3) 0.0405(19) Uani 1 1 d . . . . .
H30 H 0.1563 0.0573 0.4877 0.049 Uiso 1 1 calc R U . . .
C31 C 0.2617(9) 0.2117(7) 0.4491(3) 0.0371(17) Uani 1 1 d . . . . .
H31 H 0.2489 0.2483 0.4786 0.044 Uiso 1 1 calc R U . . .
C32 C 0.3354(9) 0.2711(7) 0.4011(3) 0.0297(16) Uani 1 1 d . . . . .
H32 H 0.3751 0.3478 0.3980 0.036 Uiso 1 1 calc R U . . .
C33 C 0.4923(7) 0.7654(5) 0.2453(2) 0.0174(11) Uani 1 1 d . . . . .
H33A H 0.4472 0.8299 0.2603 0.021 Uiso 1 1 calc R U . . .
H33B H 0.6084 0.7765 0.2404 0.021 Uiso 1 1 calc R U . . .
C34 C 0.4511(7) 0.6507(5) 0.2841(2) 0.0183(11) Uani 1 1 d . . . . .
H34A H 0.3358 0.6365 0.2861 0.022 Uiso 1 1 calc R U . . .
H34B H 0.5041 0.5872 0.2704 0.022 Uiso 1 1 calc R U . . .
C35 C 0.4999(8) 0.6485(6) 0.3397(2) 0.0236(13) Uani 1 1 d . . . . .
C36 C 0.5924(10) 0.5593(7) 0.3651(3) 0.0395(18) Uani 1 1 d . . . . .
H36 H 0.6334 0.5030 0.3466 0.047 Uiso 1 1 calc R U . . .
C37 C 0.6242(15) 0.5529(10) 0.4174(4) 0.060(3) Uani 1 1 d . . . . .
H37 H 0.6837 0.4898 0.4348 0.072 Uiso 1 1 calc R U . . .
C38 C 0.5735(14) 0.6340(11) 0.4447(4) 0.061(3) Uani 1 1 d . . . . .
H38 H 0.5973 0.6282 0.4806 0.073 Uiso 1 1 calc R U . . .
C39 C 0.4865(13) 0.7251(11) 0.4192(4) 0.066(3) Uani 1 1 d . . . . .
H39 H 0.4530 0.7840 0.4374 0.079 Uiso 1 1 calc R U . . .
C40 C 0.4475(11) 0.7315(9) 0.3673(4) 0.043(2) Uani 1 1 d . . . . .
H40 H 0.3844 0.7931 0.3506 0.052 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 O2 1.499(4) . ?
P1 O3 1.511(4) . ?
P1 O1 1.584(3) . ?
P1 C1 1.845(5) . ?
P2 O6 1.525(3) . ?
P2 O5 1.527(4) . ?
P2 O4 1.531(4) . ?
P2 C1 1.870(5) . ?
P3 O9 1.502(4) . ?
P3 O10 1.514(4) . ?
P3 O8 1.583(4) . ?
P3 C5 1.850(5) . ?
P4 O11 1.525(4) . ?
P4 O13 1.527(4) . ?
P4 O12 1.531(4) . ?
P4 C5 1.868(5) . ?
O7 C1 1.451(6) . ?
O14 C5 1.447(6) . ?
N1 C4 1.499(7) . ?
N2 C8 1.495(7) . ?
N3 C9 1.480(7) . ?
N4 C17 1.504(6) . ?
N5 C25 1.487(7) . ?
N6 C33 1.489(7) . ?
C1 C2 1.523(7) . ?
C2 C3 1.533(7) . ?
C3 C4 1.516(7) . ?
C5 C6 1.525(7) . ?
C6 C7 1.537(7) . ?
C7 C8 1.500(7) . ?
C9 C10 1.515(7) . ?
C10 C11 1.514(8) . ?
C11 C12 1.391(11) . ?
C11 C16 1.399(10) . ?
C12 C13 1.371(12) . ?
C13 C14 1.376(14) . ?
C14 C15 1.370(13) . ?
C15 C16 1.385(10) . ?
C17 C18 1.523(7) . ?
C18 C19 1.509(8) . ?
C19 C20 1.374(10) . ?
C19 C24 1.395(10) . ?
C20 C21 1.397(11) . ?
C21 C22 1.380(15) . ?
C22 C23 1.374(15) . ?
C23 C24 1.385(12) . ?
C25 C26 1.525(8) . ?
C26 C27 1.513(9) . ?
C27 C32 1.388(11) . ?
C27 C28 1.392(10) . ?
C28 C29 1.395(11) . ?
C29 C30 1.376(13) . ?
C30 C31 1.393(12) . ?
C31 C32 1.381(10) . ?
C33 C34 1.518(7) . ?
C34 C35 1.516(8) . ?
C35 C40 1.383(11) . ?
C35 C36 1.392(10) . ?
C36 C37 1.379(13) . ?
C37 C38 1.357(19) . ?
C38 C39 1.379(18) . ?
C39 C40 1.388(13) . ?

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 P1 O3 115.4(2) . . ?
O2 P1 O1 107.7(2) . . ?
O3 P1 O1 110.8(2) . . ?
O2 P1 C1 110.5(2) . . ?
O3 P1 C1 108.3(2) . . ?
O1 P1 C1 103.6(2) . . ?
O6 P2 O5 112.4(2) . . ?
O6 P2 O4 112.6(2) . . ?
O5 P2 O4 111.1(2) . . ?
O6 P2 C1 109.1(2) . . ?
O5 P2 C1 105.1(2) . . ?
O4 P2 C1 106.0(2) . . ?
O9 P3 O10 114.4(2) . . ?
O9 P3 O8 107.8(2) . . ?
O10 P3 O8 111.1(2) . . ?
O9 P3 C5 110.9(2) . . ?
O10 P3 C5 108.6(2) . . ?
O8 P3 C5 103.4(2) . . ?
O11 P4 O13 112.5(2) . . ?
O11 P4 O12 111.6(2) . . ?
O13 P4 O12 112.4(2) . . ?
O11 P4 C5 106.0(2) . . ?
O13 P4 C5 109.3(2) . . ?
O12 P4 C5 104.7(2) . . ?
O7 C1 C2 112.2(4) . . ?
O7 C1 P1 103.2(3) . . ?
C2 C1 P1 113.6(4) . . ?
O7 C1 P2 107.2(3) . . ?
C2 C1 P2 109.0(3) . . ?
P1 C1 P2 111.4(2) . . ?
C1 C2 C3 115.5(4) . . ?
C4 C3 C2 108.8(4) . . ?
N1 C4 C3 112.0(4) . . ?
O14 C5 C6 112.1(4) . . ?
O14 C5 P3 103.0(3) . . ?
C6 C5 P3 113.2(4) . . ?
O14 C5 P4 107.5(3) . . ?
C6 C5 P4 109.2(3) . . ?
P3 C5 P4 111.5(2) . . ?
C5 C6 C7 115.9(4) . . ?
C8 C7 C6 109.1(4) . . ?
N2 C8 C7 112.2(4) . . ?
N3 C9 C10 111.6(4) . . ?
C11 C10 C9 109.6(5) . . ?
C12 C11 C16 118.4(6) . . ?
C12 C11 C10 120.4(6) . . ?
C16 C11 C10 121.0(6) . . ?
C13 C12 C11 120.3(7) . . ?
C12 C13 C14 121.1(8) . . ?
C15 C14 C13 119.6(8) . . ?
C14 C15 C16 120.3(7) . . ?
C15 C16 C11 120.4(7) . . ?
N4 C17 C18 111.7(4) . . ?
C19 C18 C17 111.3(5) . . ?
C20 C19 C24 118.3(6) . . ?
C20 C19 C18 121.2(6) . . ?
C24 C19 C18 120.5(6) . . ?
C19 C20 C21 121.3(8) . . ?
C22 C21 C20 119.5(8) . . ?
C23 C22 C21 119.7(7) . . ?
C22 C23 C24 120.6(9) . . ?
C23 C24 C19 120.5(8) . . ?
N5 C25 C26 111.1(5) . . ?
C27 C26 C25 109.8(5) . . ?
C32 C27 C28 119.1(7) . . ?
C32 C27 C26 121.2(6) . . ?
C28 C27 C26 119.6(6) . . ?
C27 C28 C29 120.2(7) . . ?
C30 C29 C28 120.3(8) . . ?
C29 C30 C31 119.5(7) . . ?
C32 C31 C30 120.3(7) . . ?
C31 C32 C27 120.5(7) . . ?
N6 C33 C34 111.3(4) . . ?
C35 C34 C33 112.6(5) . . ?
C40 C35 C36 118.6(7) . . ?
C40 C35 C34 121.0(7) . . ?
C36 C35 C34 120.4(6) . . ?
C37 C36 C35 119.6(9) . . ?
C38 C37 C36 122.1(10) . . ?
C37 C38 C39 118.6(9) . . ?
C38 C39 C40 120.5(10) . . ?
C35 C40 C39 120.4(9) . . ?

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
N1 H1N O18 0.91(3) 1.94(4) 2.789(6) 156(6) .
N1 H2N O13 0.90(3) 1.94(3) 2.827(5) 168(6) 2_665
N1 H2N O16 0.90(3) 2.65(6) 3.187(6) 119(5) 2_665
N1 H3N O16 0.90(3) 1.86(3) 2.762(6) 176(6) 1_455
N2 H4N O15 0.91(3) 1.89(3) 2.788(6) 168(6) 1_665
N2 H5N O17 0.90(3) 1.87(3) 2.777(6) 177(6) 1_655
N2 H6N O6 0.91(3) 1.93(3) 2.834(5) 170(6) 2_765
N3 H7N O3 0.92(3) 2.00(4) 2.878(6) 160(6) .
N3 H8N O9 0.91(3) 2.03(5) 2.775(6) 138(6) 1_445
N3 H8N O14 0.91(3) 2.36(5) 3.068(6) 135(6) 1_445
N3 H9N O4 0.91(3) 1.85(4) 2.733(6) 164(7) 1_455
N4 H10N O10 0.91(3) 1.99(4) 2.830(6) 153(6) .
N4 H11N O5 0.91(3) 1.95(4) 2.825(6) 161(6) .
N4 H12N O2 0.91(3) 1.86(3) 2.761(6) 172(7) 1_655
N5 H13N O10 0.91(3) 1.98(3) 2.879(6) 171(6) 1_455
N5 H14N O2 0.91(3) 1.96(5) 2.771(6) 147(6) .
N5 H14N O7 0.91(3) 2.42(6) 3.078(6) 129(6) .
N5 H15N O11 0.92(3) 1.82(3) 2.735(6) 176(6) .
N6 H16N O3 0.90(3) 1.98(4) 2.830(6) 158(6) 1_565
N6 H17N O12 0.91(3) 1.94(3) 2.824(6) 164(6) .
N6 H18N O9 0.90(3) 1.86(3) 2.759(6) 171(7) 1_455
O1 H1C O4 0.85(3) 1.81(4) 2.563(5) 146(6) .
O7 H7C O13 0.84(3) 2.10(4) 2.890(5) 155(6) .
O8 H8C O11 0.86(3) 1.77(4) 2.563(5) 151(6) .
O14 H14C O6 0.84(3) 2.12(4) 2.904(5) 155(6) 1_565
O15 H15C O5 0.87(3) 1.86(3) 2.723(5) 170(7) 1_455
O15 H15D O3 0.87(3) 1.95(3) 2.804(5) 171(7) .
O16 H16C O13 0.90(3) 1.89(5) 2.709(5) 150(7) .
O16 H16D O5 0.89(3) 1.85(3) 2.738(5) 174(7) .
O17 H17C O12 0.83(5) 1.96(6) 2.734(5) 155(7) .
O17 H17D O6 0.82(5) 1.93(5) 2.700(5) 157(8) 1_565
O18 H18C O12 0.87(3) 1.86(3) 2.729(5) 171(7) .
O18 H18D O10 0.85(3) 1.96(3) 2.794(5) 167(6) 1_455

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 1553748'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N O7 P2, C6 H16 N2, 3(H2 O)'
_chemical_formula_sum            'C10 H33 N3 O10 P2'
_chemical_formula_weight         417.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.0822(6)
_cell_length_b                   16.2842(10)
_cell_length_c                   16.4233(10)
_cell_angle_alpha                89.909(5)
_cell_angle_beta                 82.523(6)
_cell_angle_gamma                87.458(6)
_cell_volume                     1876.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2596
_cell_measurement_theta_min      3.8070
_cell_measurement_theta_max      66.5490

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.610
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.82261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            23559
_diffrn_reflns_av_R_equivalents  0.1270
_diffrn_reflns_av_sigmaI/netI    0.1893
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.833
_diffrn_reflns_theta_max         67.012
_diffrn_reflns_theta_full        67.012
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6835
_reflns_number_gt                4325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 1.171.38.43d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6835
_refine_ls_number_parameters     554
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4694 18532 5027 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.5306 0 5027 nmt 1.0008 -0.0001 -0.0000 0.2025 -0.9995 0.0019 0.6004 -0.0018
-0.9995
_oxdiff_twin_integration_method  simultaneous
_twin_special_details            
;
Component 2 rotated by -179.9009° 
 around [0.95 0.10 0.29] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;

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 0.72641(16) 1.03043(6) 0.36943(6) 0.0217(2) Uani 1 1 d . . . . .
P2 P 0.89768(15) 1.18197(6) 0.28414(6) 0.0208(2) Uani 1 1 d . . . . .
P3 P 0.77673(16) 0.63113(6) 0.03286(6) 0.0208(2) Uani 1 1 d . . . . .
P4 P 0.55235(15) 0.71820(6) 0.18185(6) 0.0201(2) Uani 1 1 d . . . . .
O1 O 0.8140(4) 0.95456(16) 0.40627(17) 0.0259(7) Uani 1 1 d . . . . .
O2 O 0.6687(5) 1.09762(16) 0.43476(18) 0.0278(7) Uani 1 1 d . . . . .
O3 O 0.5625(4) 1.01304(18) 0.32308(18) 0.0284(7) Uani 1 1 d . . . . .
O4 O 0.8773(5) 1.21540(16) 0.37518(18) 0.0272(7) Uani 1 1 d D . . . .
H4 H 0.804(7) 1.182(3) 0.403(3) 0.041 Uiso 1 1 d D U . . .
O5 O 1.0804(4) 1.21394(16) 0.24045(18) 0.0258(7) Uani 1 1 d . . . . .
O6 O 0.7226(4) 1.20193(17) 0.24354(18) 0.0283(7) Uani 1 1 d . . . . .
O7 O 1.1003(4) 1.05904(16) 0.33146(17) 0.0217(6) Uani 1 1 d D . . . .
H7 H 1.096(8) 1.0142(19) 0.358(3) 0.033 Uiso 1 1 d D U . . .
O8 O 0.7142(4) 0.59087(16) -0.04185(17) 0.0257(7) Uani 1 1 d . . . . .
O9 O 0.7932(4) 0.56865(16) 0.10235(17) 0.0240(6) Uani 1 1 d . . . . .
O10 O 0.9560(4) 0.67829(16) 0.01405(18) 0.0267(7) Uani 1 1 d . . . . .
O11 O 0.5293(4) 0.62722(16) 0.21492(17) 0.0245(6) Uani 1 1 d D . . . .
H11 H 0.615(6) 0.599(3) 0.182(3) 0.037 Uiso 1 1 d D U . . .
O12 O 0.7296(4) 0.75364(16) 0.20588(17) 0.0248(6) Uani 1 1 d . . . . .
O13 O 0.3701(4) 0.76670(17) 0.21079(17) 0.0254(6) Uani 1 1 d . . . . .
O14 O 0.3988(4) 0.66949(16) 0.05638(17) 0.0226(6) Uani 1 1 d D . . . .
H14 H 0.411(8) 0.646(3) 0.0096(18) 0.034 Uiso 1 1 d D U . . .
O15 O 0.2724(4) 0.92973(17) 0.40530(19) 0.0264(7) Uani 1 1 d D . . . .
H1W H 0.367(5) 0.958(3) 0.386(3) 0.040 Uiso 1 1 d D U . . .
H2W H 0.284(8) 0.928(3) 0.4564(15) 0.040 Uiso 1 1 d D U . . .
O16 O 0.1536(5) 0.77800(18) 0.36485(19) 0.0306(7) Uani 1 1 d D . . . .
H3W H 0.182(8) 0.8256(19) 0.379(3) 0.046 Uiso 1 1 d D U . . .
H4W H 0.213(8) 0.764(3) 0.318(2) 0.046 Uiso 1 1 d D U . . .
O17 O 0.4858(5) 0.94077(18) 0.1838(2) 0.0356(8) Uani 1 1 d D . . . .
H5W H 0.515(9) 0.952(4) 0.231(2) 0.053 Uiso 1 1 d D U . . .
H6W H 0.446(9) 0.8917(19) 0.188(4) 0.053 Uiso 1 1 d D U . . .
O18 O 0.4453(5) 0.64173(19) -0.22675(19) 0.0319(7) Uani 1 1 d D . . . .
H7W H 0.376(7) 0.629(3) -0.183(2) 0.048 Uiso 1 1 d D U . . .
H8W H 0.387(8) 0.688(2) -0.233(3) 0.048 Uiso 1 1 d D U . . .
O19 O 0.2607(5) 0.59626(17) -0.07645(18) 0.0276(7) Uani 1 1 d D . . . .
H9W H 0.243(8) 0.5445(14) -0.077(3) 0.041 Uiso 1 1 d D U . . .
H10W H 0.161(5) 0.619(3) -0.049(3) 0.041 Uiso 1 1 d D U . . .
O20 O 0.0926(5) 0.81599(19) -0.0617(2) 0.0352(8) Uani 1 1 d D . . . .
H11W H 0.040(8) 0.770(2) -0.051(4) 0.053 Uiso 1 1 d D U . . .
H12W H 0.133(9) 0.805(4) -0.1121(17) 0.053 Uiso 1 1 d D U . . .
N1 N 1.0649(6) 0.8099(2) 0.1257(2) 0.0260(8) Uani 1 1 d D . . . .
H1N H 0.957(5) 0.788(3) 0.152(3) 0.039 Uiso 1 1 d D U . . .
H2N H 1.108(8) 0.795(3) 0.0727(16) 0.039 Uiso 1 1 d D U . . .
H3N H 1.165(5) 0.794(3) 0.151(3) 0.039 Uiso 1 1 d D U . . .
N2 N 0.7592(6) 0.8000(2) 0.3669(2) 0.0257(8) Uani 1 1 d D . . . .
H4N H 0.769(8) 0.8549(14) 0.370(3) 0.039 Uiso 1 1 d D U . . .
H5N H 0.886(4) 0.783(3) 0.365(3) 0.039 Uiso 1 1 d D U . . .
H6N H 0.726(8) 0.784(3) 0.318(2) 0.039 Uiso 1 1 d D U . . .
N3 N 0.7262(5) 0.8611(2) 0.5429(2) 0.0232(8) Uani 1 1 d D . . . .
H7N H 0.802(6) 0.866(3) 0.583(2) 0.035 Uiso 1 1 d D U . . .
H8N H 0.601(4) 0.879(3) 0.560(3) 0.035 Uiso 1 1 d D U . . .
H9N H 0.773(7) 0.896(2) 0.503(2) 0.035 Uiso 1 1 d D U . . .
N4 N 0.5855(6) 0.8744(2) -0.1901(2) 0.0250(8) Uani 1 1 d D . . . .
H10N H 0.803(8) 0.624(3) -0.1414(13) 0.037 Uiso 1 1 d D U . . .
H11N H 0.890(7) 0.677(2) -0.208(3) 0.037 Uiso 1 1 d D U . . .
H12N H 0.710(4) 0.637(3) -0.214(3) 0.037 Uiso 1 1 d D U . . .
N5 N 0.8293(6) 0.6297(2) -0.1973(2) 0.0252(8) Uani 1 1 d D . . . .
H13N H 0.780(7) 0.499(2) -0.103(3) 0.038 Uiso 1 1 d D U . . .
H14N H 0.955(4) 0.439(3) -0.126(3) 0.038 Uiso 1 1 d D U . . .
H15N H 0.756(7) 0.410(2) -0.127(3) 0.038 Uiso 1 1 d D U . . .
N6 N 0.8302(6) 0.4545(2) -0.1347(2) 0.0236(8) Uani 1 1 d D . . . .
H16N H 0.700(4) 0.849(3) -0.211(3) 0.035 Uiso 1 1 d D U . . .
H17N H 0.487(5) 0.846(3) -0.207(3) 0.035 Uiso 1 1 d D U . . .
H18N H 0.585(8) 0.9260(16) -0.209(3) 0.035 Uiso 1 1 d D U . . .
C1 C 0.9253(6) 1.0689(2) 0.2960(3) 0.0208(9) Uani 1 1 d . . . . .
C2 C 0.9434(6) 1.0285(2) 0.2116(2) 0.0201(8) Uani 1 1 d . . . . .
H2A H 1.0471 1.0541 0.1753 0.024 Uiso 1 1 calc R U . . .
H2B H 0.8234 1.0398 0.1878 0.024 Uiso 1 1 calc R U . . .
C3 C 0.9849(7) 0.9347(2) 0.2119(3) 0.0250(9) Uani 1 1 d . . . . .
H3A H 1.0910 0.9219 0.2443 0.030 Uiso 1 1 calc R U . . .
H3B H 0.8708 0.9074 0.2385 0.030 Uiso 1 1 calc R U . . .
C4 C 1.0373(7) 0.9017(2) 0.1255(3) 0.0258(9) Uani 1 1 d . . . . .
H4A H 0.9349 0.9177 0.0921 0.031 Uiso 1 1 calc R U . . .
H4B H 1.1562 0.9262 0.1001 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6293(7) 0.7668(3) 0.4383(3) 0.0269(9) Uani 1 1 d . . . . .
H5 H 0.5089 0.8020 0.4460 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5800(7) 0.6804(3) 0.4177(3) 0.0285(10) Uani 1 1 d . . . . .
H6A H 0.6989 0.6475 0.3996 0.034 Uiso 1 1 calc R U . . .
H6B H 0.5027 0.6825 0.3716 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4692(8) 0.6385(3) 0.4909(3) 0.0343(11) Uani 1 1 d . . . . .
H7A H 0.3452 0.6685 0.5065 0.041 Uiso 1 1 calc R U . . .
H7B H 0.4442 0.5815 0.4760 0.041 Uiso 1 1 calc R U . . .
C8 C 0.5840(8) 0.6376(3) 0.5626(3) 0.0363(11) Uani 1 1 d . . . . .
H8A H 0.7066 0.6064 0.5472 0.044 Uiso 1 1 calc R U . . .
H8B H 0.5130 0.6096 0.6099 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6225(7) 0.7248(2) 0.5874(3) 0.0267(10) Uani 1 1 d . . . . .
H9A H 0.7020 0.7225 0.6327 0.032 Uiso 1 1 calc R U . . .
H9B H 0.5002 0.7541 0.6077 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7241(7) 0.7723(2) 0.5157(3) 0.0274(10) Uani 1 1 d . . . . .
H10 H 0.8585 0.7498 0.5037 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5749(6) 0.7053(2) 0.0701(2) 0.0213(9) Uani 1 1 d . . . . .
C12 C 0.5892(6) 0.7897(2) 0.0273(2) 0.0210(9) Uani 1 1 d . . . . .
H12A H 0.4801 0.8258 0.0514 0.025 Uiso 1 1 calc R U . . .
H12B H 0.7071 0.8147 0.0397 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5910(6) 0.7881(2) -0.0654(3) 0.0230(9) Uani 1 1 d . . . . .
H13A H 0.7121 0.7614 -0.0915 0.028 Uiso 1 1 calc R U . . .
H13B H 0.4849 0.7555 -0.0794 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5706(7) 0.8749(2) -0.0983(3) 0.0261(9) Uani 1 1 d . . . . .
H14A H 0.4456 0.9002 -0.0750 0.031 Uiso 1 1 calc R U . . .
H14B H 0.6716 0.9085 -0.0810 0.031 Uiso 1 1 calc R U . . .
C15 C 0.9464(7) 0.5589(2) -0.2384(3) 0.0250(9) Uani 1 1 d . . . . .
H15 H 1.0695 0.5527 -0.2149 0.030 Uiso 1 1 calc R U . . .
C16 C 0.9869(7) 0.5788(3) -0.3290(3) 0.0296(10) Uani 1 1 d . . . . .
H16A H 1.0756 0.6244 -0.3361 0.035 Uiso 1 1 calc R U . . .
H16B H 0.8665 0.5981 -0.3489 0.035 Uiso 1 1 calc R U . . .
C17 C 1.0730(7) 0.5062(3) -0.3813(3) 0.0325(11) Uani 1 1 d . . . . .
H17A H 1.2007 0.4904 -0.3664 0.039 Uiso 1 1 calc R U . . .
H17B H 1.0879 0.5217 -0.4400 0.039 Uiso 1 1 calc R U . . .
C18 C 0.9435(7) 0.4336(3) -0.3674(3) 0.0319(10) Uani 1 1 d . . . . .
H18A H 0.8158 0.4491 -0.3824 0.038 Uiso 1 1 calc R U . . .
H18B H 0.9976 0.3865 -0.4023 0.038 Uiso 1 1 calc R U . . .
C19 C 0.9268(7) 0.4093(2) -0.2774(3) 0.0256(9) Uani 1 1 d . . . . .
H19A H 1.0550 0.3943 -0.2626 0.031 Uiso 1 1 calc R U . . .
H19B H 0.8478 0.3606 -0.2683 0.031 Uiso 1 1 calc R U . . .
C20 C 0.8362(7) 0.4803(2) -0.2228(3) 0.0245(9) Uani 1 1 d . . . . .
H20 H 0.7026 0.4914 -0.2349 0.029 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 O3 1.506(3) . ?
P1 O1 1.518(3) . ?
P1 O2 1.538(3) . ?
P1 C1 1.861(4) . ?
P2 O6 1.505(3) . ?
P2 O5 1.509(3) . ?
P2 O4 1.578(3) . ?
P2 C1 1.855(4) . ?
P3 O10 1.511(3) . ?
P3 O8 1.517(3) . ?
P3 O9 1.540(3) . ?
P3 C11 1.870(4) . ?
P4 O12 1.503(3) . ?
P4 O13 1.505(3) . ?
P4 O11 1.585(3) . ?
P4 C11 1.833(4) . ?
O7 C1 1.439(5) . ?
O14 C11 1.444(5) . ?
N1 C4 1.500(5) . ?
N2 C5 1.509(6) . ?
N3 C10 1.516(5) . ?
N4 C14 1.497(6) . ?
N5 C15 1.498(6) . ?
N6 C20 1.501(6) . ?
C1 C2 1.524(6) . ?
C2 C3 1.542(5) . ?
C3 C4 1.514(6) . ?
C5 C6 1.514(6) . ?
C5 C10 1.518(6) . ?
C6 C7 1.525(6) . ?
C7 C8 1.516(7) . ?
C8 C9 1.523(6) . ?
C9 C10 1.525(6) . ?
C11 C12 1.544(5) . ?
C12 C13 1.521(6) . ?
C13 C14 1.520(6) . ?
C15 C16 1.515(6) . ?
C15 C20 1.534(6) . ?
C16 C17 1.521(6) . ?
C17 C18 1.527(7) . ?
C18 C19 1.520(6) . ?
C19 C20 1.530(6) . ?

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 O1 113.92(17) . . ?
O3 P1 O2 110.92(18) . . ?
O1 P1 O2 111.35(16) . . ?
O3 P1 C1 108.78(18) . . ?
O1 P1 C1 103.78(18) . . ?
O2 P1 C1 107.63(17) . . ?
O6 P2 O5 115.11(17) . . ?
O6 P2 O4 112.31(17) . . ?
O5 P2 O4 106.65(17) . . ?
O6 P2 C1 109.08(18) . . ?
O5 P2 C1 109.39(17) . . ?
O4 P2 C1 103.67(17) . . ?
O10 P3 O8 113.81(16) . . ?
O10 P3 O9 111.52(17) . . ?
O8 P3 O9 111.39(15) . . ?
O10 P3 C11 108.56(16) . . ?
O8 P3 C11 104.30(18) . . ?
O9 P3 C11 106.71(17) . . ?
O12 P4 O13 114.92(16) . . ?
O12 P4 O11 110.97(17) . . ?
O13 P4 O11 107.66(16) . . ?
O12 P4 C11 110.10(18) . . ?
O13 P4 C11 109.28(18) . . ?
O11 P4 C11 103.25(16) . . ?
O7 C1 C2 111.2(3) . . ?
O7 C1 P2 102.9(2) . . ?
C2 C1 P2 109.1(3) . . ?
O7 C1 P1 109.2(3) . . ?
C2 C1 P1 113.4(3) . . ?
P2 C1 P1 110.6(2) . . ?
C1 C2 C3 114.3(3) . . ?
C4 C3 C2 111.1(3) . . ?
N1 C4 C3 110.9(3) . . ?
N2 C5 C6 108.8(3) . . ?
N2 C5 C10 109.3(4) . . ?
C6 C5 C10 113.7(3) . . ?
C5 C6 C7 112.0(4) . . ?
C8 C7 C6 109.5(4) . . ?
C7 C8 C9 110.7(4) . . ?
C8 C9 C10 111.9(4) . . ?
N3 C10 C5 110.2(3) . . ?
N3 C10 C9 107.4(3) . . ?
C5 C10 C9 112.9(4) . . ?
O14 C11 C12 109.3(3) . . ?
O14 C11 P4 104.0(3) . . ?
C12 C11 P4 110.3(3) . . ?
O14 C11 P3 108.4(2) . . ?
C12 C11 P3 113.3(3) . . ?
P4 C11 P3 111.1(2) . . ?
C13 C12 C11 115.5(3) . . ?
C14 C13 C12 110.5(3) . . ?
N4 C14 C13 110.9(3) . . ?
N5 C15 C16 107.5(3) . . ?
N5 C15 C20 108.9(3) . . ?
C16 C15 C20 112.4(3) . . ?
C15 C16 C17 113.4(4) . . ?
C16 C17 C18 109.7(4) . . ?
C19 C18 C17 108.9(4) . . ?
C18 C19 C20 110.5(3) . . ?
N6 C20 C19 108.4(3) . . ?
N6 C20 C15 110.5(3) . . ?
C19 C20 C15 111.7(4) . . ?

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 O2 0.86(2) 1.75(2) 2.586(4) 164(5) .
O7 H7 O15 0.85(2) 2.04(4) 2.746(4) 140(5) 1_655
O7 H7 O1 0.85(2) 2.30(5) 2.858(4) 123(4) .
O11 H11 O9 0.88(2) 1.75(2) 2.602(4) 165(5) .
O14 H14 O19 0.85(2) 2.06(4) 2.793(4) 143(5) .
O14 H14 O8 0.85(2) 2.34(5) 2.837(4) 117(4) .
O15 H1W O3 0.85(2) 1.88(2) 2.721(4) 168(5) .
O15 H2W O2 0.85(2) 1.90(2) 2.745(4) 168(5) 2_676
O16 H3W O15 0.85(2) 1.91(2) 2.755(4) 174(6) .
O16 H4W O13 0.86(2) 1.96(3) 2.785(4) 163(5) .
O17 H5W O3 0.85(2) 1.89(3) 2.701(4) 161(6) .
O17 H6W O13 0.86(2) 2.15(2) 3.002(4) 173(6) .
O18 H7W O19 0.85(2) 1.91(2) 2.755(4) 170(6) .
O18 H8W O6 0.85(2) 1.94(2) 2.790(4) 174(6) 2_675
O19 H9W O9 0.86(2) 1.93(2) 2.771(4) 168(5) 2_665
O19 H10W O10 0.86(2) 1.90(2) 2.751(4) 173(5) 1_455
O20 H11W O10 0.85(2) 1.91(3) 2.717(4) 157(6) 1_455
O20 H12W O6 0.86(2) 2.27(2) 3.110(4) 169(6) 2_675
N1 H1N O12 0.91(2) 1.84(2) 2.754(5) 175(5) .
N1 H2N O20 0.92(2) 2.25(3) 3.060(5) 147(5) 1_655
N1 H2N O10 0.92(2) 2.48(5) 3.012(5) 118(4) .
N1 H3N O13 0.90(2) 1.89(2) 2.788(5) 176(5) 1_655
N2 H4N O1 0.90(2) 1.78(3) 2.657(4) 162(5) .
N2 H5N O16 0.93(2) 1.89(3) 2.796(5) 164(5) 1_655
N2 H6N O12 0.91(2) 1.91(3) 2.787(5) 164(5) .
N3 H7N O7 0.91(2) 2.07(3) 2.876(4) 148(4) 2_776
N3 H8N O2 0.93(2) 1.92(2) 2.824(5) 164(5) 2_676
N3 H9N O1 0.90(2) 1.86(2) 2.729(4) 163(5) .
N5 H10N O8 0.92(2) 1.77(2) 2.661(4) 164(5) .
N5 H11N O5 0.90(2) 1.87(3) 2.723(4) 157(5) 2_775
N5 H12N O18 0.92(2) 1.91(2) 2.822(5) 168(5) .
N6 H13N O8 0.92(2) 1.82(2) 2.730(4) 172(5) .
N6 H14N O9 0.93(2) 1.88(2) 2.796(5) 168(5) 2_765
N6 H15N O14 0.92(2) 2.00(3) 2.847(4) 153(5) 2_665
N4 H16N O5 0.92(2) 1.84(2) 2.747(5) 171(5) 2_775
N4 H17N O6 0.92(2) 1.88(2) 2.797(5) 175(5) 2_675
N4 H18N O17 0.90(2) 2.23(3) 3.029(5) 148(4) 2_675
N4 H18N O3 0.90(2) 2.45(4) 3.105(5) 131(4) 2_675

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.093

