# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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 2327316'
loop_
_audit_author_name
_audit_author_address
'Jawher Makhlouf'
;university of carthage
Tunisia
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'H O10 P3, 4(C6 H14 N), 2(H2 O)'
_chemical_formula_sum            'C24 H61 N4 O12 P3'
_chemical_formula_weight         690.67

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                   9.7371(2)
_cell_length_b                   12.1048(2)
_cell_length_c                   15.7768(3)
_cell_angle_alpha                71.092(2)
_cell_angle_beta                 83.1310(10)
_cell_angle_gamma                87.2900(10)
_cell_volume                     1746.50(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    44198
_cell_measurement_theta_min      2.9860
_cell_measurement_theta_max      78.8960

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.082
_shelx_estimated_absorpt_T_min   0.603
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            72331
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         79.090
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7303
_reflns_number_gt                6733
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    SHELXL-2019/2
_computing_publication_material  SHELXL-2019/2
_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)+(0.0447P)²+0.7680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         7303
_refine_ls_number_parameters     439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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 0.32311(3) 0.75390(3) 0.51656(2) 0.01495(8) Uani 1 1 d . . . . .
P2 P 0.61870(3) 0.78167(3) 0.44356(2) 0.01490(8) Uani 1 1 d . . . . .
P3 P 0.80051(3) 0.59651(3) 0.54216(2) 0.01554(9) Uani 1 1 d . . . . .
O1 O 0.23133(10) 0.82919(8) 0.44876(7) 0.0192(2) Uani 1 1 d . . . . .
O2 O 0.34468(10) 0.63053(8) 0.51297(7) 0.0195(2) Uani 1 1 d . . . . .
O3 O 0.28465(10) 0.76086(8) 0.61045(7) 0.0194(2) Uani 1 1 d . . . . .
O4 O 0.47459(9) 0.81772(8) 0.48629(7) 0.0184(2) Uani 1 1 d . . . . .
O5 O 0.60519(11) 0.74414(9) 0.36452(7) 0.0225(2) Uani 1 1 d . . . . .
O6 O 0.71198(9) 0.88276(8) 0.42897(7) 0.0181(2) Uani 1 1 d . . . . .
O7 O 0.65920(9) 0.67285(8) 0.52681(6) 0.0178(2) Uani 1 1 d . . . . .
O8 O 0.91862(10) 0.67760(8) 0.52570(7) 0.0201(2) Uani 1 1 d . . . . .
O9 O 0.82036(10) 0.53779(9) 0.46656(7) 0.0195(2) Uani 1 1 d . . . . .
H9 H 0.768(2) 0.4815(18) 0.4739(13) 0.029 Uiso 1 1 d . U . . .
O10 O 0.76857(10) 0.50821(8) 0.63348(7) 0.0196(2) Uani 1 1 d . . . . .
N1 N 0.09704(13) 0.70018(11) 0.37058(8) 0.0183(2) Uani 1 1 d . . . . .
H1D H 0.1435(19) 0.6368(16) 0.3627(12) 0.022 Uiso 1 1 d . U . . .
H1E H 0.0341(19) 0.6754(15) 0.4211(13) 0.022 Uiso 1 1 d . U . . .
H1F H 0.1528(19) 0.7448(16) 0.3852(12) 0.022 Uiso 1 1 d . U . . .
C1 C 0.02980(14) 0.76743(12) 0.28912(9) 0.0183(3) Uani 1 1 d . . . . .
H1 H -0.048531 0.814130 0.307657 0.022 Uiso 1 1 calc R U . . .
C2 C 0.13279(16) 0.85089(13) 0.22159(11) 0.0259(3) Uani 1 1 d . . . . .
H2A H 0.213643 0.806395 0.205033 0.031 Uiso 1 1 calc R U . . .
H2B H 0.165802 0.906088 0.249121 0.031 Uiso 1 1 calc R U . . .
C3 C 0.06508(19) 0.91888(15) 0.13704(12) 0.0341(4) Uani 1 1 d . . . . .
H3A H -0.009389 0.969785 0.152703 0.041 Uiso 1 1 calc R U . . .
H3B H 0.134762 0.969342 0.092058 0.041 Uiso 1 1 calc R U . . .
C4 C 0.0046(2) 0.83604(16) 0.09616(11) 0.0368(4) Uani 1 1 d . . . . .
H4A H -0.044125 0.882112 0.044167 0.044 Uiso 1 1 calc R U . . .
H4B H 0.080596 0.791925 0.073801 0.044 Uiso 1 1 calc R U . . .
C5 C -0.09601(18) 0.75062(15) 0.16484(11) 0.0315(3) Uani 1 1 d . . . . .
H5A H -0.128227 0.694964 0.137455 0.038 Uiso 1 1 calc R U . . .
H5B H -0.177684 0.794004 0.181771 0.038 Uiso 1 1 calc R U . . .
C6 C -0.02817(16) 0.68324(13) 0.24912(10) 0.0233(3) Uani 1 1 d . . . . .
H6A H -0.097247 0.632139 0.294159 0.028 Uiso 1 1 calc R U . . .
H6B H 0.047356 0.633181 0.233492 0.028 Uiso 1 1 calc R U . . .
N1A N 0.44174(13) 0.91163(10) 0.65336(8) 0.0178(2) Uani 1 1 d . . . . .
H1G H 0.530(2) 0.9204(15) 0.6254(12) 0.021 Uiso 1 1 d . U . . .
H1H H 0.3994(19) 0.9785(17) 0.6298(12) 0.021 Uiso 1 1 d . U . . .
H1I H 0.4000(18) 0.8546(16) 0.6413(12) 0.021 Uiso 1 1 d . U . . .
C1A C 0.44161(14) 0.88840(12) 0.75201(9) 0.0191(3) Uani 1 1 d . . . . .
H1A H 0.494021 0.814158 0.777246 0.023 Uiso 1 1 calc R U . . .
C2A C 0.51394(17) 0.98677(13) 0.76882(10) 0.0270(3) Uani 1 1 d . . . . .
H2C H 0.468742 1.062178 0.739179 0.032 Uiso 1 1 calc R U . . .
H2D H 0.611675 0.990404 0.742236 0.032 Uiso 1 1 calc R U . . .
C3A C 0.5080(2) 0.96734(15) 0.87004(11) 0.0340(4) Uani 1 1 d . . . . .
H3C H 0.562048 0.896378 0.898482 0.041 Uiso 1 1 calc R U . . .
H3D H 0.550385 1.034572 0.879488 0.041 Uiso 1 1 calc R U . . .
C4A C 0.3596(2) 0.95352(18) 0.91462(12) 0.0418(5) Uani 1 1 d . . . . .
H4C H 0.307982 1.027464 0.890660 0.050 Uiso 1 1 calc R U . . .
H4D H 0.359188 0.936782 0.980372 0.050 Uiso 1 1 calc R U . . .
C5A C 0.2880(2) 0.85482(19) 0.89728(12) 0.0417(4) Uani 1 1 d . . . . .
H5C H 0.190207 0.851036 0.923702 0.050 Uiso 1 1 calc R U . . .
H5D H 0.333288 0.779624 0.927364 0.050 Uiso 1 1 calc R U . . .
C6A C 0.29389(16) 0.87240(16) 0.79664(11) 0.0307(3) Uani 1 1 d . . . . .
H6C H 0.253563 0.803757 0.788004 0.037 Uiso 1 1 calc R U . . .
H6D H 0.238054 0.942011 0.767796 0.037 Uiso 1 1 calc R U . . .
N1B N 0.51781(13) 0.54166(11) 0.35429(8) 0.0183(2) Uani 1 1 d . . . . .
H1J H 0.5357(18) 0.6055(16) 0.3696(12) 0.022 Uiso 1 1 d . U . . .
H1K H 0.5590(19) 0.4810(16) 0.3924(12) 0.022 Uiso 1 1 d . U . . .
H1L H 0.433(2) 0.5301(16) 0.3606(12) 0.022 Uiso 1 1 d . U . . .
C1B C 0.57069(15) 0.56097(12) 0.25828(9) 0.0195(3) Uani 1 1 d . . . . .
H1B H 0.671926 0.577599 0.249905 0.023 Uiso 1 1 calc R U . . .
C2B C 0.55010(18) 0.45292(13) 0.23240(10) 0.0272(3) Uani 1 1 d . . . . .
H2E H 0.450809 0.432577 0.243577 0.033 Uiso 1 1 calc R U . . .
H2F H 0.602029 0.386241 0.269862 0.033 Uiso 1 1 calc R U . . .
C3B C 0.6011(2) 0.47585(16) 0.13259(11) 0.0372(4) Uani 1 1 d . . . . .
H3E H 0.702156 0.489213 0.122827 0.045 Uiso 1 1 calc R U . . .
H3F H 0.583748 0.406225 0.115678 0.045 Uiso 1 1 calc R U . . .
C4B C 0.52827(19) 0.58208(15) 0.07235(11) 0.0326(4) Uani 1 1 d . . . . .
H4E H 0.567597 0.597399 0.008819 0.039 Uiso 1 1 calc R U . . .
H4F H 0.428651 0.565270 0.076876 0.039 Uiso 1 1 calc R U . . .
C5B C 0.54486(19) 0.68957(14) 0.09955(11) 0.0311(4) Uani 1 1 d . . . . .
H5E H 0.490068 0.754901 0.063042 0.037 Uiso 1 1 calc R U . . .
H5F H 0.643247 0.712797 0.086989 0.037 Uiso 1 1 calc R U . . .
C6B C 0.49706(17) 0.66690(13) 0.19957(10) 0.0262(3) Uani 1 1 d . . . . .
H6E H 0.516059 0.736432 0.216149 0.031 Uiso 1 1 calc R U . . .
H6F H 0.395977 0.653795 0.210675 0.031 Uiso 1 1 calc R U . . .
N1C N 0.99907(13) 0.79763(11) 0.63215(8) 0.0192(2) Uani 1 1 d . . . . .
H1M H 0.9803(19) 0.8722(17) 0.6162(12) 0.023 Uiso 1 1 d . U . . .
H1N H 0.9734(18) 0.7661(16) 0.5907(12) 0.023 Uiso 1 1 d . U . . .
H1O H 1.094(2) 0.7897(15) 0.6323(12) 0.023 Uiso 1 1 d . U . . .
C1C C 0.92182(16) 0.73587(13) 0.72121(10) 0.0245(3) Uani 1 1 d . . . . .
H1C H 0.826459 0.720165 0.710685 0.029 Uiso 1 1 calc R U . . .
C2C C 0.99267(19) 0.61848(13) 0.76226(11) 0.0309(3) Uani 1 1 d . . . . .
H2G H 1.089568 0.631281 0.769704 0.037 Uiso 1 1 calc R U . . .
H2H H 0.993825 0.571133 0.721447 0.037 Uiso 1 1 calc R U . . .
C3C C 0.9148(2) 0.55295(16) 0.85430(13) 0.0433(4) Uani 1 1 d . . . . .
H3G H 0.821052 0.533141 0.845769 0.052 Uiso 1 1 calc R U . . .
H3H H 0.964372 0.479112 0.882127 0.052 Uiso 1 1 calc R U . . .
C4C C 0.9030(2) 0.62655(18) 0.91707(12) 0.0431(4) Uani 1 1 d . . . . .
H4G H 0.996425 0.640064 0.930313 0.052 Uiso 1 1 calc R U . . .
H4H H 0.848606 0.583857 0.974699 0.052 Uiso 1 1 calc R U . . .
C5C C 0.8330(2) 0.74359(17) 0.87445(12) 0.0405(4) Uani 1 1 d . . . . .
H5G H 0.830990 0.791398 0.914988 0.049 Uiso 1 1 calc R U . . .
H5H H 0.736235 0.730215 0.867076 0.049 Uiso 1 1 calc R U . . .
C6C C 0.90889(18) 0.80991(14) 0.78273(11) 0.0305(3) Uani 1 1 d . . . . .
H6G H 0.857594 0.882790 0.754935 0.037 Uiso 1 1 calc R U . . .
H6H H 1.002196 0.831366 0.790758 0.037 Uiso 1 1 calc R U . . .
O11 O 0.72103(10) 0.93395(9) 0.58848(7) 0.0210(2) Uani 1 1 d . . . . .
H11A H 0.727(2) 0.9241(18) 0.5405(15) 0.031 Uiso 1 1 d . U . . .
H11B H 0.737(2) 1.0068(19) 0.5732(13) 0.031 Uiso 1 1 d . U . . .
O12 O 0.98693(11) 0.95765(9) 0.40197(8) 0.0260(2) Uani 1 1 d . . . . .
H12A H 0.910(2) 0.9251(19) 0.4155(15) 0.039 Uiso 1 1 d . U . . .
H12B H 1.049(2) 0.9085(19) 0.4271(14) 0.039 Uiso 1 1 d . 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 1.5121(10) . ?
P1 O1 1.5144(9) . ?
P1 O2 1.5166(9) . ?
P1 O4 1.6433(10) . ?
P2 O5 1.4801(10) . ?
P2 O6 1.4993(9) . ?
P2 O4 1.5875(10) . ?
P2 O7 1.6029(10) . ?
P3 O8 1.4912(10) . ?
P3 O10 1.4970(10) . ?
P3 O9 1.5641(10) . ?
P3 O7 1.6187(9) . ?
O9 H9 0.84(2) . ?
N1 C1 1.4886(17) . ?
N1 H1D 0.907(19) . ?
N1 H1E 0.92(2) . ?
N1 H1F 0.882(19) . ?
C1 C2 1.518(2) . ?
C1 C6 1.5205(18) . ?
C1 H1 1.0000 . ?
C2 C3 1.529(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.528(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.525(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N1A C1A 1.4891(17) . ?
N1A H1G 0.909(19) . ?
N1A H1H 0.879(19) . ?
N1A H1I 0.899(19) . ?
C1A C6A 1.516(2) . ?
C1A C2A 1.5208(19) . ?
C1A H1A 1.0000 . ?
C2A C3A 1.531(2) . ?
C2A H2C 0.9900 . ?
C2A H2D 0.9900 . ?
C3A C4A 1.521(3) . ?
C3A H3C 0.9900 . ?
C3A H3D 0.9900 . ?
C4A C5A 1.524(3) . ?
C4A H4C 0.9900 . ?
C4A H4D 0.9900 . ?
C5A C6A 1.526(2) . ?
C5A H5C 0.9900 . ?
C5A H5D 0.9900 . ?
C6A H6C 0.9900 . ?
C6A H6D 0.9900 . ?
N1B C1B 1.4865(18) . ?
N1B H1J 0.911(19) . ?
N1B H1K 0.897(19) . ?
N1B H1L 0.84(2) . ?
C1B C2B 1.519(2) . ?
C1B C6B 1.5226(19) . ?
C1B H1B 1.0000 . ?
C2B C3B 1.532(2) . ?
C2B H2E 0.9900 . ?
C2B H2F 0.9900 . ?
C3B C4B 1.531(2) . ?
C3B H3E 0.9900 . ?
C3B H3F 0.9900 . ?
C4B C5B 1.517(2) . ?
C4B H4E 0.9900 . ?
C4B H4F 0.9900 . ?
C5B C6B 1.529(2) . ?
C5B H5E 0.9900 . ?
C5B H5F 0.9900 . ?
C6B H6E 0.9900 . ?
C6B H6F 0.9900 . ?
N1C C1C 1.4895(19) . ?
N1C H1M 0.871(19) . ?
N1C H1N 0.919(19) . ?
N1C H1O 0.927(19) . ?
C1C C6C 1.512(2) . ?
C1C C2C 1.527(2) . ?
C1C H1C 1.0000 . ?
C2C C3C 1.536(2) . ?
C2C H2G 0.9900 . ?
C2C H2H 0.9900 . ?
C3C C4C 1.524(3) . ?
C3C H3G 0.9900 . ?
C3C H3H 0.9900 . ?
C4C C5C 1.525(3) . ?
C4C H4G 0.9900 . ?
C4C H4H 0.9900 . ?
C5C C6C 1.527(2) . ?
C5C H5G 0.9900 . ?
C5C H5H 0.9900 . ?
C6C H6G 0.9900 . ?
C6C H6H 0.9900 . ?
O11 H11A 0.80(2) . ?
O11 H11B 0.85(2) . ?
O12 H12A 0.83(2) . ?
O12 H12B 0.87(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 O1 113.01(6) . . ?
O3 P1 O2 114.19(6) . . ?
O1 P1 O2 114.04(5) . . ?
O3 P1 O4 103.08(5) . . ?
O1 P1 O4 104.40(5) . . ?
O2 P1 O4 106.75(5) . . ?
O5 P2 O6 117.01(6) . . ?
O5 P2 O4 112.62(6) . . ?
O6 P2 O4 104.89(5) . . ?
O5 P2 O7 110.53(5) . . ?
O6 P2 O7 110.43(5) . . ?
O4 P2 O7 99.91(5) . . ?
O8 P3 O10 119.45(6) . . ?
O8 P3 O9 107.08(6) . . ?
O10 P3 O9 111.52(6) . . ?
O8 P3 O7 108.64(5) . . ?
O10 P3 O7 103.50(5) . . ?
O9 P3 O7 105.81(5) . . ?
P2 O4 P1 132.88(6) . . ?
P2 O7 P3 131.11(6) . . ?
P3 O9 H9 115.8(13) . . ?
C1 N1 H1D 111.4(11) . . ?
C1 N1 H1E 112.1(11) . . ?
H1D N1 H1E 108.4(16) . . ?
C1 N1 H1F 111.1(12) . . ?
H1D N1 H1F 110.5(16) . . ?
H1E N1 H1F 103.0(16) . . ?
N1 C1 C2 109.92(11) . . ?
N1 C1 C6 109.49(11) . . ?
C2 C1 C6 111.81(12) . . ?
N1 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
C6 C1 H1 108.5 . . ?
C1 C2 C3 110.22(12) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 111.02(13) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 111.53(14) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.23(13) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C1 C6 C5 110.25(12) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C1A N1A H1G 110.6(11) . . ?
C1A N1A H1H 109.3(12) . . ?
H1G N1A H1H 105.8(16) . . ?
C1A N1A H1I 112.0(11) . . ?
H1G N1A H1I 109.5(16) . . ?
H1H N1A H1I 109.3(16) . . ?
N1A C1A C6A 109.18(11) . . ?
N1A C1A C2A 110.02(12) . . ?
C6A C1A C2A 112.33(13) . . ?
N1A C1A H1A 108.4 . . ?
C6A C1A H1A 108.4 . . ?
C2A C1A H1A 108.4 . . ?
C1A C2A C3A 110.62(13) . . ?
C1A C2A H2C 109.5 . . ?
C3A C2A H2C 109.5 . . ?
C1A C2A H2D 109.5 . . ?
C3A C2A H2D 109.5 . . ?
H2C C2A H2D 108.1 . . ?
C4A C3A C2A 111.18(14) . . ?
C4A C3A H3C 109.4 . . ?
C2A C3A H3C 109.4 . . ?
C4A C3A H3D 109.4 . . ?
C2A C3A H3D 109.4 . . ?
H3C C3A H3D 108.0 . . ?
C3A C4A C5A 111.04(14) . . ?
C3A C4A H4C 109.4 . . ?
C5A C4A H4C 109.4 . . ?
C3A C4A H4D 109.4 . . ?
C5A C4A H4D 109.4 . . ?
H4C C4A H4D 108.0 . . ?
C4A C5A C6A 111.60(16) . . ?
C4A C5A H5C 109.3 . . ?
C6A C5A H5C 109.3 . . ?
C4A C5A H5D 109.3 . . ?
C6A C5A H5D 109.3 . . ?
H5C C5A H5D 108.0 . . ?
C1A C6A C5A 111.02(13) . . ?
C1A C6A H6C 109.4 . . ?
C5A C6A H6C 109.4 . . ?
C1A C6A H6D 109.4 . . ?
C5A C6A H6D 109.4 . . ?
H6C C6A H6D 108.0 . . ?
C1B N1B H1J 109.5(11) . . ?
C1B N1B H1K 112.9(12) . . ?
H1J N1B H1K 106.1(15) . . ?
C1B N1B H1L 108.3(12) . . ?
H1J N1B H1L 110.6(16) . . ?
H1K N1B H1L 109.4(17) . . ?
N1B C1B C2B 110.69(12) . . ?
N1B C1B C6B 108.82(12) . . ?
C2B C1B C6B 111.37(12) . . ?
N1B C1B H1B 108.6 . . ?
C2B C1B H1B 108.6 . . ?
C6B C1B H1B 108.6 . . ?
C1B C2B C3B 109.87(13) . . ?
C1B C2B H2E 109.7 . . ?
C3B C2B H2E 109.7 . . ?
C1B C2B H2F 109.7 . . ?
C3B C2B H2F 109.7 . . ?
H2E C2B H2F 108.2 . . ?
C4B C3B C2B 111.45(14) . . ?
C4B C3B H3E 109.3 . . ?
C2B C3B H3E 109.3 . . ?
C4B C3B H3F 109.3 . . ?
C2B C3B H3F 109.3 . . ?
H3E C3B H3F 108.0 . . ?
C5B C4B C3B 111.21(13) . . ?
C5B C4B H4E 109.4 . . ?
C3B C4B H4E 109.4 . . ?
C5B C4B H4F 109.4 . . ?
C3B C4B H4F 109.4 . . ?
H4E C4B H4F 108.0 . . ?
C4B C5B C6B 111.44(13) . . ?
C4B C5B H5E 109.3 . . ?
C6B C5B H5E 109.3 . . ?
C4B C5B H5F 109.3 . . ?
C6B C5B H5F 109.3 . . ?
H5E C5B H5F 108.0 . . ?
C1B C6B C5B 111.27(13) . . ?
C1B C6B H6E 109.4 . . ?
C5B C6B H6E 109.4 . . ?
C1B C6B H6F 109.4 . . ?
C5B C6B H6F 109.4 . . ?
H6E C6B H6F 108.0 . . ?
C1C N1C H1M 110.4(12) . . ?
C1C N1C H1N 108.0(11) . . ?
H1M N1C H1N 110.4(16) . . ?
C1C N1C H1O 113.0(11) . . ?
H1M N1C H1O 106.9(16) . . ?
H1N N1C H1O 108.1(16) . . ?
N1C C1C C6C 111.51(12) . . ?
N1C C1C C2C 108.81(12) . . ?
C6C C1C C2C 112.48(13) . . ?
N1C C1C H1C 108.0 . . ?
C6C C1C H1C 108.0 . . ?
C2C C1C H1C 108.0 . . ?
C1C C2C C3C 109.82(14) . . ?
C1C C2C H2G 109.7 . . ?
C3C C2C H2G 109.7 . . ?
C1C C2C H2H 109.7 . . ?
C3C C2C H2H 109.7 . . ?
H2G C2C H2H 108.2 . . ?
C4C C3C C2C 111.19(15) . . ?
C4C C3C H3G 109.4 . . ?
C2C C3C H3G 109.4 . . ?
C4C C3C H3H 109.4 . . ?
C2C C3C H3H 109.4 . . ?
H3G C3C H3H 108.0 . . ?
C3C C4C C5C 110.86(16) . . ?
C3C C4C H4G 109.5 . . ?
C5C C4C H4G 109.5 . . ?
C3C C4C H4H 109.5 . . ?
C5C C4C H4H 109.5 . . ?
H4G C4C H4H 108.1 . . ?
C4C C5C C6C 111.40(15) . . ?
C4C C5C H5G 109.3 . . ?
C6C C5C H5G 109.3 . . ?
C4C C5C H5H 109.3 . . ?
C6C C5C H5H 109.3 . . ?
H5G C5C H5H 108.0 . . ?
C1C C6C C5C 110.59(14) . . ?
C1C C6C H6G 109.5 . . ?
C5C C6C H6G 109.5 . . ?
C1C C6C H6H 109.5 . . ?
C5C C6C H6H 109.5 . . ?
H6G C6C H6H 108.1 . . ?
H11A O11 H11B 101.5(19) . . ?
H12A O12 H12B 109(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 P2 O4 P1 49.12(10) . . . . ?
O6 P2 O4 P1 177.44(8) . . . . ?
O7 P2 O4 P1 -68.16(9) . . . . ?
O3 P1 O4 P2 131.12(9) . . . . ?
O1 P1 O4 P2 -110.59(9) . . . . ?
O2 P1 O4 P2 10.51(10) . . . . ?
O5 P2 O7 P3 69.43(9) . . . . ?
O6 P2 O7 P3 -61.65(9) . . . . ?
O4 P2 O7 P3 -171.73(8) . . . . ?
O8 P3 O7 P2 52.48(10) . . . . ?
O10 P3 O7 P2 -179.60(8) . . . . ?
O9 P3 O7 P2 -62.20(9) . . . . ?
N1 C1 C2 C3 179.08(12) . . . . ?
C6 C1 C2 C3 57.26(16) . . . . ?
C1 C2 C3 C4 -55.61(19) . . . . ?
C2 C3 C4 C5 55.1(2) . . . . ?
C3 C4 C5 C6 -55.20(19) . . . . ?
N1 C1 C6 C5 -179.32(12) . . . . ?
C2 C1 C6 C5 -57.25(16) . . . . ?
C4 C5 C6 C1 55.66(18) . . . . ?
N1A C1A C2A C3A 177.05(12) . . . . ?
C6A C1A C2A C3A 55.20(17) . . . . ?
C1A C2A C3A C4A -55.58(18) . . . . ?
C2A C3A C4A C5A 56.01(19) . . . . ?
C3A C4A C5A C6A -55.5(2) . . . . ?
N1A C1A C6A C5A -176.96(14) . . . . ?
C2A C1A C6A C5A -54.64(18) . . . . ?
C4A C5A C6A C1A 54.4(2) . . . . ?
N1B C1B C2B C3B 178.28(13) . . . . ?
C6B C1B C2B C3B 57.08(17) . . . . ?
C1B C2B C3B C4B -56.65(19) . . . . ?
C2B C3B C4B C5B 55.6(2) . . . . ?
C3B C4B C5B C6B -54.1(2) . . . . ?
N1B C1B C6B C5B -178.70(12) . . . . ?
C2B C1B C6B C5B -56.41(17) . . . . ?
C4B C5B C6B C1B 54.62(18) . . . . ?
N1C C1C C2C C3C -179.98(14) . . . . ?
C6C C1C C2C C3C 55.95(19) . . . . ?
C1C C2C C3C C4C -55.8(2) . . . . ?
C2C C3C C4C C5C 56.4(2) . . . . ?
C3C C4C C5C C6C -56.0(2) . . . . ?
N1C C1C C6C C5C -178.41(13) . . . . ?
C2C C1C C6C C5C -55.85(18) . . . . ?
C4C C5C C6C C1C 55.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9 O2 0.84(2) 1.73(2) 2.5684(13) 178(2) 2_666 yes
N1 H1D O10 0.907(19) 1.903(19) 2.8021(16) 170.6(17) 2_666 yes
N1 H1E O8 0.92(2) 1.89(2) 2.7706(17) 159.6(16) 1_455 yes
N1 H1F O1 0.882(19) 1.885(19) 2.7380(15) 162.0(17) . yes
N1A H1G O11 0.909(19) 1.88(2) 2.7822(16) 169.6(16) . yes
N1A H1H O6 0.879(19) 1.979(19) 2.8530(15) 172.5(17) 2_676 yes
N1A H1I O3 0.899(19) 1.843(19) 2.7279(15) 167.8(16) . yes
N1B H1J O5 0.911(19) 1.813(19) 2.6914(16) 161.2(17) . yes
N1B H1K O2 0.897(19) 1.960(19) 2.8462(16) 169.3(16) 2_666 yes
N1B H1L O10 0.84(2) 2.02(2) 2.8517(16) 173.7(17) 2_666 yes
N1C H1M O12 0.871(19) 2.02(2) 2.8409(16) 156.3(16) 2_776 yes
N1C H1N O8 0.919(19) 1.839(19) 2.7476(16) 169.2(17) . yes
N1C H1O O3 0.927(19) 1.882(19) 2.7932(16) 166.9(16) 1_655 yes
O11 H11A O6 0.80(2) 2.00(2) 2.7917(15) 170(2) . yes
O11 H11B O1 0.85(2) 1.93(2) 2.7839(14) 174.2(19) 2_676 yes
O12 H12A O6 0.83(2) 1.99(2) 2.8066(14) 167(2) . yes
O12 H12B O1 0.87(2) 1.99(2) 2.8200(15) 161(2) 1_655 yes

_refine_diff_density_max         0.587
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.051



