# Supplementary Information (SI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2434790'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2025-03-27 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H13 N2 O5 P'
_chemical_formula_weight         212.14

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

_cell_length_a                   6.1084(3)
_cell_length_b                   8.9906(5)
_cell_length_c                   15.9200(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     874.30(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      27.88

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.310
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9257
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5 (Krause et al., 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 3'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48153
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.418
_diffrn_reflns_theta_max         27.944
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2086
_reflns_number_gt                1995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_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       'APEX3 v2017.3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT v8.37a (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37a (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury 2021.3.0 (Macrae et al. 2020)'
_computing_publication_material  'PublCIF v1.9.21_c (Westrip, 2010)'
_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)+(0.0472P)²+0.1429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 799 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2086
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.69835(9) 0.68146(6) 0.70742(4) 0.01151(16) Uani 1 1 d . . . . .
O1 O 0.4754(3) 0.6586(2) 0.53430(11) 0.0210(4) Uani 1 1 d . . . . .
O2 O 0.8256(3) 0.80755(18) 0.66967(10) 0.0178(4) Uani 1 1 d . . . . .
O3 O 0.4534(3) 0.7319(2) 0.71566(11) 0.0167(4) Uani 1 1 d . . . . .
H3O H 0.380(8) 0.677(5) 0.752(3) 0.067(14) Uiso 1 1 d . . . . .
O4 O 0.7791(3) 0.62181(17) 0.79012(10) 0.0151(3) Uani 1 1 d . . . . .
N1 N 0.7626(3) 0.5373(2) 0.47999(12) 0.0146(4) Uani 1 1 d . . . . .
N2 N 0.7123(4) 0.6048(2) 0.40147(12) 0.0132(4) Uani 1 1 d . . . . .
H2N1 H 0.809(5) 0.681(3) 0.3955(18) 0.014(6) Uiso 1 1 d . . . . .
H2N2 H 0.726(6) 0.550(4) 0.356(2) 0.027(8) Uiso 1 1 d . . . . .
H2N3 H 0.586(6) 0.634(4) 0.405(2) 0.025(8) Uiso 1 1 d . . . . .
C1 C 0.6396(4) 0.5816(2) 0.54585(14) 0.0142(5) Uani 1 1 d . . . . .
C2 C 0.7102(4) 0.5275(2) 0.63211(13) 0.0141(4) Uani 1 1 d . . . . .
H2 H 0.603700 0.449738 0.650776 0.017 Uiso 1 1 calc R U . . .
C3 C 0.9407(4) 0.4596(3) 0.63555(15) 0.0204(5) Uani 1 1 d . . . . .
H3A H 1.050299 0.540456 0.638848 0.025 Uiso 1 1 calc R U . . .
H3B H 0.954573 0.398141 0.686886 0.025 Uiso 1 1 calc R U . . .
C4 C 0.9880(5) 0.3637(3) 0.55889(15) 0.0224(6) Uani 1 1 d . . . . .
H4A H 1.136248 0.320051 0.563433 0.027 Uiso 1 1 calc R U . . .
H4B H 0.880558 0.281483 0.555588 0.027 Uiso 1 1 calc R U . . .
C5 C 0.9731(4) 0.4590(3) 0.48089(15) 0.0184(5) Uani 1 1 d . . . . .
H5A H 1.094504 0.531892 0.480264 0.022 Uiso 1 1 calc R U . . .
H5B H 0.986050 0.395619 0.430258 0.022 Uiso 1 1 calc R U . . .
O5W O 0.2127(3) 0.6000(2) 0.81912(11) 0.0190(4) Uani 1 1 d . . . . .
H5C H 0.219(6) 0.502(4) 0.824(2) 0.037(10) Uiso 1 1 d . . . . .
H5D H 0.086(6) 0.616(4) 0.805(2) 0.030(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.5001(17) . ?
P1 O4 1.5047(17) . ?
P1 O3 1.5688(17) . ?
P1 C2 1.833(2) . ?
O1 C1 1.232(3) . ?
O3 H3O 0.89(5) . ?
N1 C1 1.350(3) . ?
N1 N2 1.423(3) . ?
N1 C5 1.466(3) . ?
N2 H2N1 0.91(3) . ?
N2 H2N2 0.88(3) . ?
N2 H2N3 0.82(4) . ?
C1 C2 1.519(3) . ?
C2 C3 1.536(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.511(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O5W H5C 0.89(4) . ?
O5W H5D 0.82(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O4 116.74(10) . . ?
O2 P1 O3 108.02(10) . . ?
O4 P1 O3 110.03(10) . . ?
O2 P1 C2 106.75(10) . . ?
O4 P1 C2 106.88(10) . . ?
O3 P1 C2 108.08(11) . . ?
P1 O3 H3O 112(3) . . ?
C1 N1 N2 115.89(18) . . ?
C1 N1 C5 128.5(2) . . ?
N2 N1 C5 113.75(18) . . ?
N1 N2 H2N1 105.8(18) . . ?
N1 N2 H2N2 118(2) . . ?
H2N1 N2 H2N2 106(3) . . ?
N1 N2 H2N3 106(2) . . ?
H2N1 N2 H2N3 113(3) . . ?
H2N2 N2 H2N3 109(3) . . ?
O1 C1 N1 120.2(2) . . ?
O1 C1 C2 123.1(2) . . ?
N1 C1 C2 116.7(2) . . ?
C1 C2 C3 114.82(19) . . ?
C1 C2 P1 109.78(15) . . ?
C3 C2 P1 108.25(16) . . ?
C1 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
P1 C2 H2 107.9 . . ?
C4 C3 C2 111.7(2) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 109.1(2) . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C4 109.4(2) . . ?
N1 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
H5C O5W H5D 104(3) . . ?

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
N2 N1 C1 O1 10.2(3) . . . . ?
C5 N1 C1 O1 173.4(2) . . . . ?
N2 N1 C1 C2 -171.81(19) . . . . ?
C5 N1 C1 C2 -8.6(3) . . . . ?
O1 C1 C2 C3 -168.6(2) . . . . ?
N1 C1 C2 C3 13.4(3) . . . . ?
O1 C1 C2 P1 -46.4(3) . . . . ?
N1 C1 C2 P1 135.60(17) . . . . ?
O2 P1 C2 C1 -52.02(19) . . . . ?
O4 P1 C2 C1 -177.63(16) . . . . ?
O3 P1 C2 C1 63.97(19) . . . . ?
O2 P1 C2 C3 74.02(17) . . . . ?
O4 P1 C2 C3 -51.60(18) . . . . ?
O3 P1 C2 C3 -170.00(15) . . . . ?
C1 C2 C3 C4 -40.0(3) . . . . ?
P1 C2 C3 C4 -163.06(19) . . . . ?
C2 C3 C4 C5 60.6(3) . . . . ?
C1 N1 C5 C4 29.1(3) . . . . ?
N2 N1 C5 C4 -167.4(2) . . . . ?
C3 C4 C5 N1 -52.7(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
O3 H3O O5W 0.89(5) 1.63(5) 2.506(2) 170(5) .
N2 H2N1 O1 0.91(3) 2.09(3) 2.855(3) 141(2) 4_566
N2 H2N1 O3 0.91(3) 2.13(3) 2.793(3) 129(2) 4_566
N2 H2N2 O4 0.88(3) 1.87(3) 2.701(3) 157(3) 2_664
N2 H2N3 O1 0.82(4) 2.17(4) 2.607(3) 113(3) .
N2 H2N3 O2 0.82(4) 2.05(4) 2.736(3) 140(3) 4_466
C4 H4B O5W 0.99 2.64 3.301(3) 124.4 3_646
C5 H5B O5W 0.99 2.55 3.255(3) 127.8 2_664
O5W H5C O2 0.89(4) 1.77(4) 2.646(2) 168(4) 3_646
O5W H5D O4 0.82(4) 1.89(4) 2.695(3) 168(3) 1_455

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.064


# start Validation Reply Form
_vrf_PLAT417_1                   
;
PROBLEM: Short Inter D-H..H-D       H3O      ..H5D      .       2.06 Ang.  
RESPONSE: This is not a D-H..H-D contact, in the sense that H5D is on 
the opposite side of the O5W molecule than the O3-H3O donor approaches. 
The O-H---O hydrogen bond here is very strong, H---A = 1.63(5) Angstroms,
which happens to bring the "H---H" distance within the tolerance for the 
alert. All H atom locations are clearly suggested by the difference 
electron density map and supported by the resulting hydrogen bonding 
interactions.
;
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2434791'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2025-03-27 deposited with the CCDC.	2025-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N O5 P'
_chemical_formula_weight         243.15

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                   8.3552(2)
_cell_length_b                   6.4722(2)
_cell_length_c                   18.7224(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.8761(9)
_cell_angle_gamma                90
_cell_volume                     1012.32(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8350
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      28.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9407
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5 (Krause et al., 2015)'
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 3'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24087
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.355
_diffrn_reflns_theta_max         28.719
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2603
_reflns_number_gt                2043
_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       'APEX3 v2017.3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT v8.37a (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37a (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury 2021.3.0 (Macrae et al. 2020)'
_computing_publication_material  'PublCIF v1.9.21_c (Westrip, 2010)'
_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)+(0.0476P)²+0.5871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2603
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.83207(5) 0.25918(7) 0.48766(3) 0.02290(16) Uani 1 1 d . . . . .
O1 O 0.78648(15) 0.4824(2) 0.48136(7) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.75849(19) 0.1156(2) 0.43147(8) 0.0366(4) Uani 1 1 d . . . . .
H2O H 0.659(4) 0.075(5) 0.4342(17) 0.077(10) Uiso 1 1 d . . . . .
O3 O 1.01486(16) 0.2257(2) 0.48003(8) 0.0293(3) Uani 1 1 d D . . . .
H3O H 1.079(3) 0.323(4) 0.4911(16) 0.070(10) Uiso 1 1 d D . . . .
O4 O 0.53572(16) -0.0229(2) 0.57528(8) 0.0323(3) Uani 1 1 d . . . . .
O5 O 0.36408(16) 0.2983(3) 0.61789(8) 0.0341(4) Uani 1 1 d . . . . .
H5O H 0.317(4) 0.376(5) 0.5858(17) 0.069(10) Uiso 1 1 d . . . . .
N1 N 0.52625(18) 0.3174(3) 0.60292(9) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.7810(2) 0.1683(3) 0.57669(10) 0.0235(4) Uani 1 1 d . . . . .
H1 H 0.829347 0.031584 0.583497 0.028 Uiso 1 1 calc R U . . .
C2 C 0.6022(2) 0.1466(3) 0.58513(10) 0.0227(4) Uani 1 1 d . . . . .
C3 C 0.5989(2) 0.5140(3) 0.62316(12) 0.0342(5) Uani 1 1 d . . . . .
H3A H 0.533779 0.580623 0.658912 0.041 Uiso 1 1 calc R U . . .
H3B H 0.602172 0.603774 0.581713 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7652(2) 0.4842(3) 0.65239(11) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.8530(2) 0.3122(3) 0.63202(10) 0.0280(4) Uani 1 1 d . . . . .
C6 C 1.0041(3) 0.2774(4) 0.66146(12) 0.0435(6) Uani 1 1 d . . . . .
H6 H 1.062419 0.161132 0.648645 0.052 Uiso 1 1 calc R U . . .
C7 C 1.0671(3) 0.4182(6) 0.71028(14) 0.0632(9) Uani 1 1 d . . . . .
H7 H 1.167866 0.394953 0.730502 0.076 Uiso 1 1 calc R U . . .
C8 C 0.9829(3) 0.5904(6) 0.72897(15) 0.0683(10) Uani 1 1 d . . . . .
H8 H 1.027739 0.684916 0.760894 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8316(3) 0.6250(4) 0.70076(13) 0.0503(7) Uani 1 1 d . . . . .
H9 H 0.774202 0.741705 0.713978 0.060 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 O1 1.4983(14) . ?
P1 O2 1.5261(15) . ?
P1 O3 1.5514(14) . ?
P1 C1 1.8242(19) . ?
O2 H2O 0.87(3) . ?
O3 H3O 0.847(18) . ?
O4 C2 1.242(2) . ?
O5 N1 1.3934(19) . ?
O5 H5O 0.87(3) . ?
N1 C2 1.320(2) . ?
N1 C3 1.458(3) . ?
C1 C5 1.511(3) . ?
C1 C2 1.512(2) . ?
C1 H1 0.9800 . ?
C3 C4 1.498(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.390(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.388(3) . ?
C6 C7 1.388(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?

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 115.71(9) . . ?
O1 P1 O3 112.15(8) . . ?
O2 P1 O3 103.77(8) . . ?
O1 P1 C1 108.67(8) . . ?
O2 P1 C1 109.64(9) . . ?
O3 P1 C1 106.45(8) . . ?
P1 O2 H2O 121(2) . . ?
P1 O3 H3O 119(2) . . ?
N1 O5 H5O 104(2) . . ?
C2 N1 O5 116.70(15) . . ?
C2 N1 C3 126.66(16) . . ?
O5 N1 C3 115.30(15) . . ?
C5 C1 C2 111.68(15) . . ?
C5 C1 P1 109.36(12) . . ?
C2 C1 P1 111.76(12) . . ?
C5 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
P1 C1 H1 108.0 . . ?
O4 C2 N1 124.16(17) . . ?
O4 C2 C1 120.47(16) . . ?
N1 C2 C1 115.36(16) . . ?
N1 C3 C4 111.27(16) . . ?
N1 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C9 119.7(2) . . ?
C5 C4 C3 119.57(18) . . ?
C9 C4 C3 120.7(2) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 C1 121.50(19) . . ?
C4 C5 C1 118.39(17) . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?

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
O1 P1 C1 C5 -52.16(14) . . . . ?
O2 P1 C1 C5 -179.52(12) . . . . ?
O3 P1 C1 C5 68.83(14) . . . . ?
O1 P1 C1 C2 72.03(14) . . . . ?
O2 P1 C1 C2 -55.33(15) . . . . ?
O3 P1 C1 C2 -166.98(12) . . . . ?
O5 N1 C2 O4 6.3(3) . . . . ?
C3 N1 C2 O4 172.40(19) . . . . ?
O5 N1 C2 C1 -173.94(15) . . . . ?
C3 N1 C2 C1 -7.9(3) . . . . ?
C5 C1 C2 O4 -142.01(18) . . . . ?
P1 C1 C2 O4 95.11(18) . . . . ?
C5 C1 C2 N1 38.2(2) . . . . ?
P1 C1 C2 N1 -84.65(18) . . . . ?
C2 N1 C3 C4 -24.7(3) . . . . ?
O5 N1 C3 C4 141.52(17) . . . . ?
N1 C3 C4 C5 25.7(3) . . . . ?
N1 C3 C4 C9 -153.1(2) . . . . ?
C9 C4 C5 C6 2.0(3) . . . . ?
C3 C4 C5 C6 -176.8(2) . . . . ?
C9 C4 C5 C1 -176.96(18) . . . . ?
C3 C4 C5 C1 4.2(3) . . . . ?
C2 C1 C5 C6 144.47(19) . . . . ?
P1 C1 C5 C6 -91.3(2) . . . . ?
C2 C1 C5 C4 -36.5(2) . . . . ?
P1 C1 C5 C4 87.69(18) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C1 C5 C6 C7 177.8(2) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C7 C8 C9 C4 -0.6(4) . . . . ?
C5 C4 C9 C8 -1.1(4) . . . . ?
C3 C4 C9 C8 177.7(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
O2 H2O O4 0.87(3) 1.67(3) 2.532(2) 169(3) 3_656
O3 H3O O1 0.847(18) 1.763(18) 2.6098(19) 177(3) 3_766
O5 H5O O1 0.87(3) 1.77(3) 2.642(2) 176(3) 3_666

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.065

