# Supplementary Information (SI) for CrystEngComm.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2385027'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P, 2H2 O'
_chemical_formula_sum            'C9 H18 N3 O10 P'
_chemical_formula_weight         359.23

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      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   4.8019(6)
_cell_length_b                   8.3731(9)
_cell_length_c                   9.5127(15)
_cell_angle_alpha                76.71(2)
_cell_angle_beta                 80.38(2)
_cell_angle_gamma                86.60(2)
_cell_volume                     366.91(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3738
_cell_measurement_theta_min      4.8260
_cell_measurement_theta_max      74.4040

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.251
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            4863
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.837
_diffrn_reflns_theta_max         74.754
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_point_group_measured_fraction_full 0.718
_reflns_number_total             2088
_reflns_number_gt                2060
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.400
_reflns_Friedel_fraction_max     0.396
_reflns_Friedel_fraction_full    0.439

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0573P)²+0.0377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2088
_refine_ls_number_parameters     217
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_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 0.31999(10) 0.17000(6) 0.69999(6) 0.01233(15) Uani 1 1 d . . . . .
O11 O 0.5609(4) 0.1665(2) 0.7826(2) 0.0164(4) Uani 1 1 d . . . . .
O12 O 0.2205(4) 0.0086(2) 0.6864(2) 0.0157(4) Uani 1 1 d . . . . .
O13 O 0.0665(4) 0.2709(2) 0.7683(2) 0.0177(4) Uani 1 1 d . . . . .
H13 H -0.086969 0.234955 0.758266 0.027 Uiso 1 1 calc R U . . .
O2 O 0.7214(4) 0.9624(2) 0.4176(2) 0.0168(4) Uani 1 1 d . . . . .
O2' O 0.4100(4) 0.7875(2) 0.1443(2) 0.0184(4) Uani 1 1 d . . . . .
H2O H 0.426994 0.889852 0.119316 0.028 Uiso 1 1 calc R U . . .
O3' O 0.6869(4) 0.4977(2) 0.1450(2) 0.0166(4) Uani 1 1 d . . . . .
H3O H 0.767355 0.404831 0.159677 0.025 Uiso 1 1 calc R U . . .
O4' O 0.1692(4) 0.6000(2) 0.4346(2) 0.0148(4) Uani 1 1 d . . . . .
O5' O 0.4287(4) 0.2828(2) 0.5423(2) 0.0143(4) Uani 1 1 d . . . . .
N1 N 0.4995(5) 0.7239(3) 0.5343(2) 0.0133(4) Uani 1 1 d . . . . .
N3 N 0.8098(5) 0.8395(3) 0.6452(2) 0.0138(4) Uani 1 1 d . . . . .
H3 H 0.944666 0.909117 0.637470 0.017 Uiso 1 1 calc R U . . .
N4 N 0.8740(5) 0.7402(3) 0.8831(2) 0.0171(5) Uani 1 1 d . . . . .
H41 H 0.997366 0.817702 0.871232 0.020 Uiso 1 1 calc R U . . .
H42 H 0.836353 0.670153 0.967914 0.020 Uiso 1 1 calc R U . . .
C2 C 0.6780(5) 0.8499(3) 0.5256(3) 0.0135(5) Uani 1 1 d . . . . .
C4 C 0.7462(6) 0.7292(3) 0.7743(3) 0.0146(5) Uani 1 1 d . . . . .
C5 C 0.5475(6) 0.6074(3) 0.7822(3) 0.0163(5) Uani 1 1 d . . . . .
H5 H 0.497513 0.526590 0.869811 0.020 Uiso 1 1 calc R U . . .
C6 C 0.4313(6) 0.6092(3) 0.6620(3) 0.0146(5) Uani 1 1 d . . . . .
H6 H 0.297921 0.528158 0.666178 0.018 Uiso 1 1 calc R U . . .
C1' C 0.3513(6) 0.7339(3) 0.4053(3) 0.0138(5) Uani 1 1 d . . . . .
H1' H 0.237825 0.838714 0.388667 0.017 Uiso 1 1 calc R U . . .
C2' C 0.5537(6) 0.7240(3) 0.2641(3) 0.0144(5) Uani 1 1 d . . . . .
H2' H 0.738109 0.777716 0.255573 0.017 Uiso 1 1 calc R U . . .
C3' C 0.5825(5) 0.5384(3) 0.2808(3) 0.0124(5) Uani 1 1 d . . . . .
H3' H 0.710808 0.491101 0.353369 0.015 Uiso 1 1 calc R U . . .
C4' C 0.2800(5) 0.4846(3) 0.3431(3) 0.0136(5) Uani 1 1 d . . . . .
H4' H 0.169242 0.499361 0.260634 0.016 Uiso 1 1 calc R U . . .
C5' C 0.2470(6) 0.3107(3) 0.4325(3) 0.0159(5) Uani 1 1 d . . . . .
H5'2 H 0.048058 0.292927 0.479825 0.019 Uiso 1 1 calc R U . . .
H5'1 H 0.297695 0.232427 0.368012 0.019 Uiso 1 1 calc R U . . .
O1W O 0.9292(4) 0.1988(2) 0.1817(2) 0.0171(4) Uani 1 1 d DG . . . .
H1W H 0.908024 0.135001 0.264792 0.026 Uiso 1 1 d DG U . . .
H2W H 0.822934 0.168379 0.131510 0.026 Uiso 1 1 d DG U . . .
O2W O 0.4655(4) 0.1203(2) 1.0698(2) 0.0178(4) Uani 1 1 d DG . . . .
H3W H 0.490587 0.138174 0.978046 0.027 Uiso 1 1 d DG U . . .
H4W H 0.295169 0.141289 1.098718 0.027 Uiso 1 1 d DG 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 O11 1.4986(19) . yes
P1 O12 1.4996(19) . yes
P1 O13 1.5761(19) . yes
P1 O5' 1.6002(19) . yes
O13 H13 0.8400 . ?
O2 C2 1.221(3) . ?
O2' C2' 1.414(3) . ?
O2' H2O 0.8400 . ?
O3' C3' 1.415(3) . ?
O3' H3O 0.8400 . ?
O4' C1' 1.411(3) . ?
O4' C4' 1.465(3) . ?
O5' C5' 1.441(3) . ?
N1 C6 1.369(3) . ?
N1 C2 1.378(3) . ?
N1 C1' 1.502(3) . ?
N3 C4 1.357(3) . ?
N3 C2 1.375(3) . ?
N3 H3 0.8800 . ?
N4 C4 1.311(4) . ?
N4 H41 0.8800 . ?
N4 H42 0.8800 . ?
C4 C5 1.419(4) . ?
C5 C6 1.351(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1' C2' 1.537(4) . ?
C1' H1' 1.0000 . ?
C2' C3' 1.526(3) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.527(4) . ?
C3' H3' 1.0000 . ?
C4' C5' 1.510(3) . ?
C4' H4' 1.0000 . ?
C5' H5'2 0.9900 . ?
C5' H5'1 0.9900 . ?
O1W H1W 0.8402 . ?
O1W H2W 0.8401 . ?
O2W H3W 0.8398 . ?
O2W H4W 0.8400 . ?

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
O11 P1 O12 117.49(11) . . ?
O11 P1 O13 108.48(11) . . ?
O12 P1 O13 110.39(10) . . ?
O11 P1 O5' 103.99(10) . . yes
O12 P1 O5' 110.83(10) . . yes
O13 P1 O5' 104.77(10) . . yes
P1 O13 H13 109.5 . . ?
C2' O2' H2O 109.5 . . ?
C3' O3' H3O 109.5 . . ?
C1' O4' C4' 110.0(2) . . ?
C5' O5' P1 118.80(17) . . ?
C6 N1 C2 121.1(2) . . ?
C6 N1 C1' 121.8(2) . . ?
C2 N1 C1' 116.5(2) . . ?
C4 N3 C2 124.5(2) . . ?
C4 N3 H3 117.7 . . ?
C2 N3 H3 117.7 . . ?
C4 N4 H41 120.0 . . ?
C4 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
O2 C2 N3 121.9(2) . . ?
O2 C2 N1 122.4(2) . . ?
N3 C2 N1 115.7(2) . . ?
N4 C4 N3 118.3(2) . . ?
N4 C4 C5 124.1(3) . . ?
N3 C4 C5 117.6(2) . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 N1 122.1(2) . . ?
C5 C6 H6 118.9 . . ?
N1 C6 H6 118.9 . . ?
O4' C1' N1 109.2(2) . . ?
O4' C1' C2' 106.3(2) . . ?
N1 C1' C2' 113.4(2) . . ?
O4' C1' H1' 109.3 . . ?
N1 C1' H1' 109.3 . . ?
C2' C1' H1' 109.3 . . ?
O2' C2' C3' 107.6(2) . . ?
O2' C2' C1' 108.2(2) . . ?
C3' C2' C1' 100.6(2) . . ?
O2' C2' H2' 113.2 . . ?
C3' C2' H2' 113.2 . . ?
C1' C2' H2' 113.2 . . ?
O3' C3' C2' 111.1(2) . . ?
O3' C3' C4' 113.8(2) . . ?
C2' C3' C4' 101.6(2) . . ?
O3' C3' H3' 110.0 . . ?
C2' C3' H3' 110.0 . . ?
C4' C3' H3' 110.0 . . ?
O4' C4' C5' 109.7(2) . . ?
O4' C4' C3' 104.5(2) . . ?
C5' C4' C3' 116.0(2) . . ?
O4' C4' H4' 108.8 . . ?
C5' C4' H4' 108.8 . . ?
C3' C4' H4' 108.8 . . ?
O5' C5' C4' 109.3(2) . . ?
O5' C5' H5'2 109.8 . . ?
C4' C5' H5'2 109.8 . . ?
O5' C5' H5'1 109.8 . . ?
C4' C5' H5'1 109.8 . . ?
H5'2 C5' H5'1 108.3 . . ?
H1W O1W H2W 108.1 . . ?
H3W O2W H4W 108.1 . . ?

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
O11 P1 O5' C5' 179.12(17) . . . . ?
O12 P1 O5' C5' 52.0(2) . . . . ?
O13 P1 O5' C5' -67.09(19) . . . . ?
C4 N3 C2 O2 171.9(2) . . . . ?
C4 N3 C2 N1 -9.5(4) . . . . ?
C6 N1 C2 O2 -172.9(2) . . . . ?
C1' N1 C2 O2 -1.9(4) . . . . ?
C6 N1 C2 N3 8.4(4) . . . . ?
C1' N1 C2 N3 179.4(2) . . . . ?
C2 N3 C4 N4 -175.1(2) . . . . ?
C2 N3 C4 C5 5.7(4) . . . . ?
N4 C4 C5 C6 -179.8(2) . . . . ?
N3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 N1 0.1(4) . . . . ?
C2 N1 C6 C5 -4.1(4) . . . . ?
C1' N1 C6 C5 -174.7(2) . . . . ?
C4' O4' C1' N1 -109.6(2) . . . . ?
C4' O4' C1' C2' 13.0(2) . . . . ?
C6 N1 C1' O4' -6.6(3) . . . . ?
C2 N1 C1' O4' -177.6(2) . . . . yes
C6 N1 C1' C2' -124.9(2) . . . . ?
C2 N1 C1' C2' 64.1(3) . . . . ?
O4' C1' C2' O2' 79.1(2) . . . . ?
N1 C1' C2' O2' -160.94(19) . . . . ?
O4' C1' C2' C3' -33.6(2) . . . . ?
N1 C1' C2' C3' 86.3(2) . . . . ?
O2' C2' C3' O3' 48.5(3) . . . . ?
C1' C2' C3' O3' 161.6(2) . . . . ?
O2' C2' C3' C4' -73.0(2) . . . . ?
C1' C2' C3' C4' 40.2(2) . . . . ?
C1' O4' C4' C5' 138.2(2) . . . . ?
C1' O4' C4' C3' 13.1(2) . . . . ?
O3' C3' C4' O4' -153.25(19) . . . . ?
C2' C3' C4' O4' -33.7(2) . . . . ?
O3' C3' C4' C5' 85.8(3) . . . . ?
C2' C3' C4' C5' -154.6(2) . . . . ?
P1 O5' C5' C4' 143.28(18) . . . . ?
O4' C4' C5' O5' -67.0(3) . . . . ?
C3' C4' C5' O5' 51.1(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

O13 H13 O11 0.84 1.78 2.601(3) 165.5 1_455
O2' H2O O2W 0.84 1.89 2.730(3) 178.1 1_564
O3' H3O O1W 0.84 1.83 2.670(3) 175.9 .
O1W H1W O2 0.84 1.94 2.719(3) 154.1 1_545
O1W H2W O2W 0.84 2.00 2.795(3) 158.8 1_554
O2W H3W O11 0.84 1.80 2.634(3) 176.4 .
O2W H4W O1W 0.84 1.88 2.720(3) 172.9 1_456
N3 H3 O12 0.88 1.78 2.626(3) 159.5 1_665
N4 H41 O12 0.88 2.25 2.965(3) 137.8 1_665
N4 H42 O3' 0.88 2.01 2.878(3) 168.7 1_556
C6 H6 O13 0.95 2.40 3.285(3) 154.2 .
C6 H6 O5' 0.95 2.59 3.195(3) 121.7 .
C2' H2' O2 1.00 2.41 2.948(3) 112.9 .

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.051


_vrf_PLAT417_I                   
;
PROBLEM: Short Inter D-H..H-D       H2W      ..H3O      .       2.05 Ang.  
RESPONSE: The short D-H..H-D distances are water...hydroxyl distances.
Adopted model for water H atoms is rational, leads to correct hydrogen bonds,
but is probably not perfect.
;
_vrf_PLAT915_I                   
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         40 %     
RESPONSE: The absolute configuration of CMP is known.
;


####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 2385028'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P, H2 O'
_chemical_formula_sum            'C9 H16 N3 O9 P'
_chemical_formula_weight         341.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           1
_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'

_cell_length_a                   4.7963(8)
_cell_length_b                   8.247(3)
_cell_length_c                   9.040(3)
_cell_angle_alpha                70.65(2)
_cell_angle_beta                 86.70(3)
_cell_angle_gamma                84.89(2)
_cell_volume                     335.89(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1530
_cell_measurement_theta_min      5.1400
_cell_measurement_theta_max      71.6500

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             178
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.368
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88944
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            3244
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.188
_diffrn_reflns_theta_max         65.976
_diffrn_reflns_theta_full        65.976
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.680
_diffrn_reflns_point_group_measured_fraction_full 0.680
_reflns_number_total             1600
_reflns_number_gt                1215
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.410
_reflns_Friedel_fraction_max     0.395
_reflns_Friedel_fraction_full    0.395

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.18(12)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1600
_refine_ls_number_parameters     203
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0980
_refine_ls_wR_factor_ref         0.2852
_refine_ls_wR_factor_gt          0.2717
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.165
_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 0.3204(6) 0.1702(4) 0.7001(4) 0.0397(10) Uani 1 1 d . . . . .
O11 O 0.241(2) 0.0089(12) 0.6765(13) 0.041(2) Uani 1 1 d . . . . .
O12 O 0.5590(18) 0.1449(14) 0.8084(12) 0.043(2) Uani 1 1 d . . . . .
O13 O 0.064(2) 0.2720(15) 0.7550(15) 0.051(3) Uani 1 1 d . . . . .
H13 H -0.043112 0.201769 0.814692 0.077 Uiso 1 1 calc R U . . .
O2 O 0.726(2) 1.0060(14) 0.3416(15) 0.054(3) Uani 1 1 d . . . . .
O2' O 0.394(2) 0.8300(16) 0.0476(15) 0.055(3) Uani 1 1 d . . . . .
H2O H 0.377523 0.937884 0.022437 0.082 Uiso 1 1 calc R U . . .
O3' O 0.692(2) 0.5008(14) 0.1234(14) 0.052(3) Uani 1 1 d . . . . .
H3O H 0.602959 0.418773 0.120237 0.078 Uiso 1 1 calc R U . . .
O4' O 0.161(2) 0.6515(14) 0.3594(14) 0.047(3) Uani 1 1 d . . . . .
O5' O 0.413(2) 0.3048(13) 0.5360(12) 0.045(3) Uani 1 1 d . . . . .
N1 N 0.501(3) 0.7617(17) 0.4688(15) 0.044(3) Uani 1 1 d . . . . .
N3 N 0.824(3) 0.8593(16) 0.5942(15) 0.043(3) Uani 1 1 d . . . . .
H3 H 0.957682 0.927458 0.589469 0.052 Uiso 1 1 calc R U . . .
N4 N 0.927(3) 0.7304(17) 0.8542(15) 0.048(3) Uani 1 1 d . . . . .
H41 H 1.053194 0.804957 0.842691 0.057 Uiso 1 1 calc R U . . .
H42 H 0.899177 0.651560 0.946094 0.057 Uiso 1 1 calc R U . . .
C2 C 0.687(3) 0.8871(19) 0.4625(18) 0.038(3) Uani 1 1 d . . . . .
C4 C 0.778(3) 0.7369(19) 0.7339(19) 0.040(3) Uani 1 1 d . . . . .
C5 C 0.578(3) 0.620(2) 0.740(2) 0.043(4) Uani 1 1 d . . . . .
H5 H 0.537144 0.530923 0.834909 0.052 Uiso 1 1 calc R U . . .
C6 C 0.445(3) 0.6395(18) 0.6072(18) 0.041(3) Uani 1 1 d . . . . .
H6 H 0.305910 0.563327 0.610961 0.049 Uiso 1 1 calc R U . . .
C1' C 0.352(3) 0.785(2) 0.3223(19) 0.044(4) Uani 1 1 d . U . . .
H1' H 0.246865 0.901079 0.286577 0.053 Uiso 1 1 calc R U . . .
C2' C 0.532(4) 0.759(2) 0.1930(19) 0.050(4) Uani 1 1 d . . . . .
H2' H 0.715322 0.810280 0.187251 0.060 Uiso 1 1 calc R U . . .
C3' C 0.573(3) 0.564(2) 0.242(2) 0.047(4) Uani 1 1 d . . . . .
H3' H 0.694599 0.520135 0.335824 0.056 Uiso 1 1 calc R U . . .
C4' C 0.272(3) 0.519(2) 0.293(2) 0.046(4) Uani 1 1 d . . . . .
H4' H 0.164567 0.532730 0.197890 0.056 Uiso 1 1 calc R U . . .
C5' C 0.244(4) 0.341(2) 0.406(2) 0.050(4) Uani 1 1 d . . . . .
H5'2 H 0.046209 0.328427 0.442710 0.060 Uiso 1 1 calc R U . . .
H5'1 H 0.296845 0.256544 0.351369 0.060 Uiso 1 1 calc R U . . .
O1W O 0.471(3) 0.2413(18) 0.0804(19) 0.071(4) Uani 1 1 d DG . . . .
H1W H 0.470498 0.168872 0.171183 0.107 Uiso 1 1 d DG U . . .
H2W H 0.383478 0.202769 0.022733 0.107 Uiso 1 1 d DG 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 O11 1.499(10) . yes
P1 O12 1.505(10) . yes
P1 O13 1.576(12) . yes
P1 O5' 1.596(11) . yes
O13 H13 0.8400 . ?
O2 C2 1.220(19) . ?
O2' C2' 1.42(2) . ?
O2' H2O 0.8400 . ?
O3' C3' 1.41(2) . ?
O3' H3O 0.8400 . ?
O4' C1' 1.436(17) . ?
O4' C4' 1.45(2) . ?
O5' C5' 1.40(2) . ?
N1 C6 1.351(19) . ?
N1 C2 1.408(18) . ?
N1 C1' 1.490(19) . ?
N3 C2 1.34(2) . ?
N3 C4 1.35(2) . ?
N3 H3 0.8800 . ?
N4 C4 1.32(2) . ?
N4 H41 0.8800 . ?
N4 H42 0.8800 . ?
C4 C5 1.40(2) . ?
C5 C6 1.35(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1' C2' 1.48(2) . ?
C1' H1' 1.0000 . ?
C2' C3' 1.52(2) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.53(2) . ?
C3' H3' 1.0000 . ?
C4' C5' 1.50(2) . ?
C4' H4' 1.0000 . ?
C5' H5'2 0.9900 . ?
C5' H5'1 0.9900 . ?
O1W H1W 0.8403 . ?
O1W H2W 0.8404 . ?

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
O11 P1 O12 114.8(6) . . ?
O11 P1 O13 112.8(6) . . ?
O12 P1 O13 109.3(7) . . ?
O11 P1 O5' 109.9(6) . . yes
O12 P1 O5' 106.6(6) . . yes
O13 P1 O5' 102.6(6) . . yes
P1 O13 H13 109.5 . . ?
C2' O2' H2O 109.5 . . ?
C3' O3' H3O 109.5 . . ?
C1' O4' C4' 109.4(12) . . ?
C5' O5' P1 119.8(10) . . ?
C6 N1 C2 119.7(12) . . ?
C6 N1 C1' 123.5(12) . . ?
C2 N1 C1' 116.4(12) . . ?
C2 N3 C4 126.5(14) . . ?
C2 N3 H3 116.8 . . ?
C4 N3 H3 116.8 . . ?
C4 N4 H41 120.0 . . ?
C4 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
O2 C2 N3 123.9(13) . . ?
O2 C2 N1 121.1(13) . . ?
N3 C2 N1 114.9(13) . . ?
N4 C4 N3 118.8(14) . . ?
N4 C4 C5 123.9(15) . . ?
N3 C4 C5 117.3(15) . . ?
C6 C5 C4 117.7(15) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 N1 123.3(13) . . ?
C5 C6 H6 118.3 . . ?
N1 C6 H6 118.3 . . ?
O4' C1' C2' 104.4(12) . . ?
O4' C1' N1 106.6(13) . . ?
C2' C1' N1 114.7(13) . . ?
O4' C1' H1' 110.3 . . ?
C2' C1' H1' 110.3 . . ?
N1 C1' H1' 110.3 . . ?
O2' C2' C1' 110.7(15) . . ?
O2' C2' C3' 111.6(12) . . ?
C1' C2' C3' 102.2(13) . . ?
O2' C2' H2' 110.7 . . ?
C1' C2' H2' 110.7 . . ?
C3' C2' H2' 110.7 . . ?
O3' C3' C2' 114.1(13) . . ?
O3' C3' C4' 115.4(13) . . ?
C2' C3' C4' 99.3(12) . . ?
O3' C3' H3' 109.2 . . ?
C2' C3' H3' 109.2 . . ?
C4' C3' H3' 109.2 . . ?
O4' C4' C5' 112.3(14) . . ?
O4' C4' C3' 104.3(12) . . ?
C5' C4' C3' 114.6(15) . . ?
O4' C4' H4' 108.5 . . ?
C5' C4' H4' 108.5 . . ?
C3' C4' H4' 108.5 . . ?
O5' C5' C4' 112.3(12) . . ?
O5' C5' H5'2 109.1 . . ?
C4' C5' H5'2 109.1 . . ?
O5' C5' H5'1 109.1 . . ?
C4' C5' H5'1 109.1 . . ?
H5'2 C5' H5'1 107.9 . . ?
H1W O1W H2W 108.0 . . ?

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
O11 P1 O5' C5' 48.7(13) . . . . ?
O12 P1 O5' C5' 173.6(12) . . . . ?
O13 P1 O5' C5' -71.5(13) . . . . ?
C4 N3 C2 O2 175.5(14) . . . . ?
C4 N3 C2 N1 -8(2) . . . . ?
C6 N1 C2 O2 -174.7(13) . . . . ?
C1' N1 C2 O2 -1(2) . . . . ?
C6 N1 C2 N3 9(2) . . . . ?
C1' N1 C2 N3 -177.9(12) . . . . ?
C2 N3 C4 N4 -177.8(14) . . . . ?
C2 N3 C4 C5 4(2) . . . . ?
N4 C4 C5 C6 -178.4(15) . . . . ?
N3 C4 C5 C6 0(2) . . . . ?
C4 C5 C6 N1 2(2) . . . . ?
C2 N1 C6 C5 -6(2) . . . . ?
C1' N1 C6 C5 -178.9(15) . . . . ?
C4' O4' C1' C2' 17.1(17) . . . . ?
C4' O4' C1' N1 -104.7(15) . . . . ?
C6 N1 C1' O4' -3(2) . . . . ?
C2 N1 C1' O4' -175.8(12) . . . . yes
C6 N1 C1' C2' -117.9(16) . . . . ?
C2 N1 C1' C2' 69.1(18) . . . . ?
O4' C1' C2' O2' 80.1(15) . . . . ?
N1 C1' C2' O2' -163.5(12) . . . . ?
O4' C1' C2' C3' -38.9(15) . . . . ?
N1 C1' C2' C3' 77.5(15) . . . . ?
O2' C2' C3' O3' 49.3(19) . . . . ?
C1' C2' C3' O3' 167.6(13) . . . . ?
O2' C2' C3' C4' -74.0(17) . . . . ?
C1' C2' C3' C4' 44.3(14) . . . . ?
C1' O4' C4' C5' 136.1(13) . . . . ?
C1' O4' C4' C3' 11.4(18) . . . . ?
O3' C3' C4' O4' -156.4(13) . . . . ?
C2' C3' C4' O4' -34.0(16) . . . . ?
O3' C3' C4' C5' 80(2) . . . . ?
C2' C3' C4' C5' -157.2(15) . . . . ?
P1 O5' C5' C4' 151.5(12) . . . . ?
O4' C4' C5' O5' -66.7(19) . . . . ?
C3' C4' C5' O5' 52(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

O13 H13 O12 0.84 2.01 2.681(13) 135.8 1_455
O2' H2O O12 0.84 2.30 2.914(17) 130.1 1_564
O3' H3O O1W 0.84 1.79 2.619(17) 167.2 .
O1W H1W O2 0.84 2.06 2.78(2) 143.5 1_545
O1W H2W O12 0.84 2.25 2.823(18) 126.0 1_554
N3 H3 O11 0.88 1.89 2.703(16) 153.6 1_665
N4 H41 O11 0.88 2.08 2.834(15) 142.7 1_665
N4 H41 O2' 0.88 2.61 3.238(17) 129.2 1_656
N4 H42 O3' 0.88 1.95 2.790(17) 158.0 1_556
C6 H6 O13 0.95 2.66 3.513(17) 150.1 .
C6 H6 O5' 0.95 2.45 3.055(16) 121.6 .
C2' H2' O2 1.00 2.46 3.018(19) 114.5 .
C3' H3' O4' 1.00 2.62 3.289(19) 124.1 1_655
C4' H4' O3' 1.00 2.46 3.29(2) 140.1 1_455
C5' H5'1 O1W 0.99 2.58 3.41(2) 141.0 .

_refine_diff_density_max         0.982
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.171


_vrf_PLAT340_II                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............       0.02 Ang.  
RESPONSE: Measured crystal was obtained by temperature-induced dehydration.
;
_vrf_PLAT915_II                  
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         40 %     
RESPONSE: Measured crystal was obtained by temperature-induced dehydration.
The absolute configuration of CMP is known.
;
####################################################################### 
# 
# 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_IX
_database_code_depnum_ccdc_archive 'CCDC 2385035'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P'
_chemical_formula_sum            'C9 H14 N3 O8 P'
_chemical_formula_weight         323.20

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           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                   8.338(2)
_cell_length_b                   31.318(7)
_cell_length_c                   4.8912(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1277.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5393
_cell_measurement_theta_min      2.6910
_cell_measurement_theta_max      74.4820

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    2.396
_shelx_estimated_absorpt_T_min   0.730
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71882
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12419
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.822
_diffrn_reflns_theta_max         75.600
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2594
_reflns_number_gt                2498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.997

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1172P)²+17.7074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0063(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 910 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.105(16)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2594
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.1197
_refine_ls_wR_factor_ref         0.3178
_refine_ls_wR_factor_gt          0.3168
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.8373(4) 0.17440(10) 0.8909(7) 0.0288(8) Uani 1 1 d . . . . .
O11 O 0.8150(11) 0.1953(3) 0.6218(19) 0.033(2) Uani 1 1 d . . . . .
O12 O 1.0085(11) 0.1683(3) 0.991(2) 0.036(2) Uani 1 1 d . . . . .
O13 O 0.7356(11) 0.2010(3) 1.105(2) 0.035(2) Uani 1 1 d . . . . .
H13 H 0.795945 0.209610 1.230781 0.052 Uiso 1 1 calc R U . . .
O2 O 0.1232(11) 0.0829(3) 0.570(2) 0.034(2) Uani 1 1 d . . . . .
O2' O 0.3709(15) 0.0090(3) 1.027(3) 0.057(4) Uani 1 1 d . . . . .
H2O H 0.355212 -0.013472 0.936840 0.086 Uiso 1 1 calc R U . . .
O3' O 0.6800(17) 0.0114(4) 0.825(2) 0.056(3) Uani 1 1 d . . . . .
H3O H 0.707938 0.006424 0.663019 0.085 Uiso 1 1 calc R U . . .
O4' O 0.4709(10) 0.0950(3) 1.166(2) 0.034(2) Uani 1 1 d . . . . .
O5' O 0.7494(12) 0.1288(3) 0.876(2) 0.035(2) Uani 1 1 d . . . . .
N1 N 0.3252(13) 0.1193(4) 0.786(2) 0.031(2) Uani 1 1 d . . . . .
N3 N 0.1771(13) 0.1502(4) 0.437(2) 0.032(2) Uani 1 1 d . . . . .
H3 H 0.111475 0.147389 0.297284 0.038 Uiso 1 1 calc R U . . .
N4 N 0.2076(15) 0.2210(4) 0.313(3) 0.038(3) Uani 1 1 d . . . . .
H41 H 0.135953 0.217656 0.182225 0.045 Uiso 1 1 calc R U . . .
H42 H 0.253508 0.246040 0.336885 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1979(13) 0.1151(4) 0.595(3) 0.031(3) Uani 1 1 d . . . . .
C4 C 0.2455(17) 0.1891(4) 0.469(3) 0.030(3) Uani 1 1 d . . . . .
C5 C 0.3650(15) 0.1930(5) 0.677(3) 0.033(3) Uani 1 1 d . . . . .
H5 H 0.419105 0.219240 0.707519 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3986(16) 0.1583(4) 0.829(3) 0.029(3) Uani 1 1 d . . . . .
H6 H 0.475865 0.160721 0.970340 0.035 Uiso 1 1 calc R U . . .
C1' C 0.3508(16) 0.0833(4) 0.975(3) 0.032(3) Uani 1 1 d . . . . .
H1' H 0.248629 0.077574 1.075355 0.039 Uiso 1 1 calc R U . . .
C2' C 0.4076(19) 0.0427(5) 0.846(4) 0.047(4) Uani 1 1 d . . . . .
H2' H 0.359889 0.038195 0.660572 0.056 Uiso 1 1 calc R U . . .
C3' C 0.5921(15) 0.0486(5) 0.834(3) 0.037(3) Uani 1 1 d . . . . .
H3' H 0.621641 0.067478 0.676523 0.044 Uiso 1 1 calc R U . . .
C4' C 0.6177(14) 0.0716(4) 1.097(3) 0.033(3) Uani 1 1 d . . . . .
H4' H 0.634750 0.049591 1.242568 0.039 Uiso 1 1 calc R U . . .
C5' C 0.7595(14) 0.1018(5) 1.106(3) 0.035(3) Uani 1 1 d . . . . .
H5'2 H 0.757107 0.118900 1.275794 0.042 Uiso 1 1 calc R U . . .
H5'1 H 0.861008 0.085436 1.100950 0.042 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 O11 1.481(9) . yes
P1 O12 1.521(10) . yes
P1 O13 1.583(10) . yes
P1 O5' 1.605(10) . yes
O13 H13 0.8400 . ?
O2 C2 1.193(15) . ?
O2' C2' 1.41(2) . ?
O2' H2O 0.8400 . ?
O3' C3' 1.378(17) . ?
O3' H3O 0.8400 . ?
O4' C1' 1.419(16) . ?
O4' C4' 1.465(15) . ?
O5' C5' 1.409(16) . ?
N1 C6 1.383(17) . ?
N1 C2 1.422(17) . ?
N1 C1' 1.470(16) . ?
N3 C2 1.353(17) . ?
N3 C4 1.355(16) . ?
N3 H3 0.8800 . ?
N4 C4 1.297(18) . ?
N4 H41 0.8800 . ?
N4 H42 0.8800 . ?
C4 C5 1.430(19) . ?
C5 C6 1.343(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1' C2' 1.50(2) . ?
C1' H1' 1.0000 . ?
C2' C3' 1.55(2) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.49(2) . ?
C3' H3' 1.0000 . ?
C4' C5' 1.514(18) . ?
C4' H4' 1.0000 . ?
C5' H5'2 0.9900 . ?
C5' H5'1 0.9900 . ?

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
O11 P1 O12 117.3(6) . . ?
O11 P1 O13 106.8(5) . . ?
O12 P1 O13 110.9(5) . . ?
O11 P1 O5' 107.1(5) . . yes
O12 P1 O5' 109.4(5) . . yes
O13 P1 O5' 104.6(5) . . yes
P1 O13 H13 109.5 . . ?
C2' O2' H2O 109.5 . . ?
C3' O3' H3O 109.5 . . ?
C1' O4' C4' 108.0(10) . . ?
C5' O5' P1 118.1(9) . . ?
C6 N1 C2 120.6(11) . . ?
C6 N1 C1' 121.3(11) . . ?
C2 N1 C1' 116.8(11) . . ?
C2 N3 C4 127.6(12) . . ?
C2 N3 H3 116.2 . . ?
C4 N3 H3 116.2 . . ?
C4 N4 H41 120.0 . . ?
C4 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
O2 C2 N3 124.2(13) . . ?
O2 C2 N1 122.3(12) . . ?
N3 C2 N1 113.4(11) . . ?
N4 C4 N3 121.5(13) . . ?
N4 C4 C5 121.7(13) . . ?
N3 C4 C5 116.8(12) . . ?
C6 C5 C4 118.0(12) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 N1 122.7(13) . . ?
C5 C6 H6 118.7 . . ?
N1 C6 H6 118.7 . . ?
O4' C1' N1 108.6(11) . . ?
O4' C1' C2' 105.9(11) . . ?
N1 C1' C2' 115.6(12) . . ?
O4' C1' H1' 108.8 . . ?
N1 C1' H1' 108.8 . . ?
C2' C1' H1' 108.8 . . ?
O2' C2' C1' 107.7(14) . . ?
O2' C2' C3' 109.2(13) . . ?
C1' C2' C3' 103.2(12) . . ?
O2' C2' H2' 112.1 . . ?
C1' C2' H2' 112.1 . . ?
C3' C2' H2' 112.1 . . ?
O3' C3' C4' 111.1(11) . . ?
O3' C3' C2' 115.3(13) . . ?
C4' C3' C2' 99.6(12) . . ?
O3' C3' H3' 110.2 . . ?
C4' C3' H3' 110.2 . . ?
C2' C3' H3' 110.2 . . ?
O4' C4' C3' 108.7(10) . . ?
O4' C4' C5' 109.5(11) . . ?
C3' C4' C5' 115.8(13) . . ?
O4' C4' H4' 107.5 . . ?
C3' C4' H4' 107.5 . . ?
C5' C4' H4' 107.5 . . ?
O5' C5' C4' 107.9(11) . . ?
O5' C5' H5'2 110.1 . . ?
C4' C5' H5'2 110.1 . . ?
O5' C5' H5'1 110.1 . . ?
C4' C5' H5'1 110.1 . . ?
H5'2 C5' H5'1 108.4 . . ?

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
O11 P1 O5' C5' 177.3(9) . . . . ?
O12 P1 O5' C5' 49.3(11) . . . . ?
O13 P1 O5' C5' -69.6(10) . . . . ?
C4 N3 C2 O2 173.1(13) . . . . ?
C4 N3 C2 N1 -10.4(18) . . . . ?
C6 N1 C2 O2 -173.6(12) . . . . ?
C1' N1 C2 O2 -6.3(19) . . . . ?
C6 N1 C2 N3 9.8(17) . . . . ?
C1' N1 C2 N3 177.2(11) . . . . ?
C2 N3 C4 N4 -175.6(12) . . . . ?
C2 N3 C4 C5 6.4(18) . . . . ?
N4 C4 C5 C6 -179.3(12) . . . . ?
N3 C4 C5 C6 -1.3(17) . . . . ?
C4 C5 C6 N1 1.5(18) . . . . ?
C2 N1 C6 C5 -6.1(18) . . . . ?
C1' N1 C6 C5 -172.9(12) . . . . ?
C4' O4' C1' N1 -106.8(12) . . . . ?
C4' O4' C1' C2' 18.0(14) . . . . ?
C6 N1 C1' O4' -6.9(16) . . . . ?
C2 N1 C1' O4' -174.2(10) . . . . yes
C6 N1 C1' C2' -125.7(13) . . . . ?
C2 N1 C1' C2' 67.0(15) . . . . ?
O4' C1' C2' O2' 80.5(13) . . . . ?
N1 C1' C2' O2' -159.2(12) . . . . ?
O4' C1' C2' C3' -34.9(15) . . . . ?
N1 C1' C2' C3' 85.4(15) . . . . ?
O2' C2' C3' O3' 41.5(19) . . . . ?
C1' C2' C3' O3' 155.9(12) . . . . ?
O2' C2' C3' C4' -77.3(14) . . . . ?
C1' C2' C3' C4' 37.0(15) . . . . ?
C1' O4' C4' C3' 6.9(14) . . . . ?
C1' O4' C4' C5' 134.3(11) . . . . ?
O3' C3' C4' O4' -149.1(12) . . . . ?
C2' C3' C4' O4' -27.2(14) . . . . ?
O3' C3' C4' C5' 87.1(16) . . . . ?
C2' C3' C4' C5' -150.9(12) . . . . ?
P1 O5' C5' C4' 156.1(9) . . . . ?
O4' C4' C5' O5' -72.5(14) . . . . ?
C3' C4' C5' O5' 50.8(15) . . . . ?

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

O13 H13 O11 0.84 1.97 2.620(13) 133.3 1_556
O2' H2O O2 0.84 2.28 2.885(13) 129.7 2
O3' H3O O3' 0.84 1.98 2.802(12) 166.1 2_654
N3 H3 O12 0.88 1.85 2.657(15) 152.1 1_454
N4 H42 O11 0.88 1.92 2.789(15) 169.5 4_456
N4 H41 O12 0.88 2.10 2.821(17) 139.1 1_454
C6 H6 O13 0.95 2.59 3.393(16) 142.3 .
C6 H6 O5' 0.95 2.53 3.076(16) 116.5 .
C1' H1' O2 1.00 2.64 3.474(17) 141.0 1_556
C2' H2' O2 1.00 2.46 3.005(19) 113.7 .
C2' H2' O2' 1.00 2.51 3.233(19) 128.6 2_554
C4' H4' O3' 1.00 2.49 3.293(16) 137.1 2_655

_refine_diff_density_max         1.306
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.185


_vrf_PLAT340_IX                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01967 Ang.  
RESPONSE: Measured crystal was obtained by temperature-induced dehydration.
;
####################################################################### 
# 
# 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_VII_HT
_database_code_depnum_ccdc_archive 'CCDC 2385033'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P, 1.5H2 O'
_chemical_formula_sum            'C9 H17 N3 O9.50 P'
_chemical_formula_weight         350.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.4629(16)
_cell_length_b                   35.212(7)
_cell_length_c                   4.8658(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1450.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6660
_cell_measurement_theta_min      2.5080
_cell_measurement_theta_max      74.6930

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    2.236
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            10362
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.510
_diffrn_reflns_theta_max         74.876
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2812
_reflns_number_gt                2712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.585
_reflns_Friedel_fraction_max     0.877
_reflns_Friedel_fraction_full    0.942

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0248P)²+2.6009P] 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 973 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2812
_refine_ls_number_parameters     231
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.092
_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 0.79839(12) 0.18113(3) 0.8903(2) 0.0234(2) Uani 1 1 d . . . . .
O11 O 0.7774(4) 0.20123(8) 0.6238(6) 0.0289(6) Uani 1 1 d . . . . .
O12 O 0.9631(4) 0.17597(9) 0.9951(6) 0.0316(7) Uani 1 1 d . . . . .
O13 O 0.6935(4) 0.20272(9) 1.1074(6) 0.0331(7) Uani 1 1 d . . . . .
H13 H 0.732602 0.199938 1.264805 0.050 Uiso 1 1 calc R U . . .
O2 O 0.0809(4) 0.10349(9) 0.5740(8) 0.0371(8) Uani 1 1 d . . . . .
O2' O 0.3216(4) 0.03456(9) 0.9616(7) 0.0386(8) Uani 1 1 d . . . . .
H2O H 0.355111 0.014338 0.890918 0.058 Uiso 1 1 calc R U . . .
O3' O 0.6212(4) 0.03580(9) 0.7425(8) 0.0370(8) Uani 1 1 d . . . . .
H3O H 0.699571 0.039097 0.639256 0.055 Uiso 1 1 calc R U . . .
O4' O 0.4398(4) 0.10955(8) 1.1395(6) 0.0293(7) Uani 1 1 d . . . . .
O5' O 0.7150(4) 0.14073(8) 0.8533(6) 0.0287(7) Uani 1 1 d . . . . .
N1 N 0.2859(4) 0.13480(10) 0.7784(7) 0.0248(7) Uani 1 1 d . . . . .
N3 N 0.1381(4) 0.16307(10) 0.4305(8) 0.0272(8) Uani 1 1 d . . . . .
H3 H 0.071444 0.160680 0.292829 0.033 Uiso 1 1 calc R U . . .
N4 N 0.1677(5) 0.22508(10) 0.3027(8) 0.0314(9) Uani 1 1 d . . . . .
H41 H 0.094321 0.221468 0.177349 0.038 Uiso 1 1 calc R U . . .
H42 H 0.212616 0.247495 0.319890 0.038 Uiso 1 1 calc R U . . .
C2 C 0.1613(5) 0.13204(11) 0.5952(10) 0.0267(8) Uani 1 1 d . . . . .
C4 C 0.2100(5) 0.19720(11) 0.4632(8) 0.0267(9) Uani 1 1 d . . . . .
C5 C 0.3281(5) 0.19986(12) 0.6682(9) 0.0283(9) Uani 1 1 d . . . . .
H5 H 0.382208 0.223080 0.700306 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3620(5) 0.16854(12) 0.8171(9) 0.0274(9) Uani 1 1 d . . . . .
H6 H 0.441806 0.170055 0.953907 0.033 Uiso 1 1 calc R U . . .
C1' C 0.3151(5) 0.10077(12) 0.9585(8) 0.0274(9) Uani 1 1 d . . . . .
H1' H 0.217536 0.094805 1.066177 0.033 Uiso 1 1 calc R U . . .
C2' C 0.3657(5) 0.06584(12) 0.7938(9) 0.0291(9) Uani 1 1 d . . . . .
H2' H 0.317263 0.064888 0.606469 0.035 Uiso 1 1 calc R U . . .
C3' C 0.5449(5) 0.07073(12) 0.7868(9) 0.0266(9) Uani 1 1 d . . . . .
H3' H 0.574472 0.089018 0.638167 0.032 Uiso 1 1 calc R U . . .
C4' C 0.5809(5) 0.08806(12) 1.0658(9) 0.0265(9) Uani 1 1 d . . . . .
H4' H 0.595361 0.067077 1.202023 0.032 Uiso 1 1 calc R U . . .
C5' C 0.7248(5) 0.11347(12) 1.0746(9) 0.0298(9) Uani 1 1 d . . . . .
H5'1 H 0.729590 0.126867 1.253234 0.036 Uiso 1 1 calc R U . . .
H5'2 H 0.821827 0.098008 1.054673 0.036 Uiso 1 1 calc R U . . .
O1W O 0.902(3) 0.0401(7) 0.529(3) 0.050(4) Uani 0.5 1 d DG . P A 1
H1W H 0.917492 0.027356 0.385650 0.074 Uiso 0.5 1 d DG U P A 1
H2W H 0.970495 0.057313 0.536050 0.074 Uiso 0.5 1 d DG U P A 1
O1X O 0.876(3) 0.0447(7) 0.432(4) 0.046(4) Uani 0.5 1 d DG . P B 2
H1X H 0.936587 0.034016 0.319535 0.069 Uiso 0.5 1 d DG U P B 2
H2X H 0.913845 0.066159 0.469668 0.069 Uiso 0.5 1 d DG U P B 2
O2W O 0.9762(15) -0.0075(4) 1.0563(17) 0.051(3) Uani 0.5 1 d DG . P C -1
H3W H 0.888978 -0.018838 1.045751 0.07(5) Uiso 0.5 1 d DG . P C -1
H4W H 0.989781 0.004586 0.909490 0.13(8) Uiso 0.5 1 d DG . 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 O11 1.488(3) . yes
P1 O12 1.495(3) . yes
P1 O13 1.575(3) . yes
P1 O5' 1.598(3) . yes
O13 H13 0.8400 . ?
O2 C2 1.218(5) . ?
O2' C2' 1.421(5) . ?
O2' H2O 0.8400 . ?
O3' C3' 1.406(5) . ?
O3' H3O 0.8400 . ?
O4' C1' 1.409(5) . ?
O4' C4' 1.459(5) . ?
O5' C5' 1.445(5) . ?
N1 C6 1.364(5) . ?
N1 C2 1.385(5) . ?
N1 C1' 1.505(5) . ?
N3 C4 1.357(5) . ?
N3 C2 1.369(5) . ?
N3 H3 0.8800 . ?
N4 C4 1.304(5) . ?
N4 H41 0.8800 . ?
N4 H42 0.8800 . ?
C4 C5 1.416(6) . ?
C5 C6 1.350(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1' C2' 1.529(6) . ?
C1' H1' 1.0000 . ?
C2' C3' 1.527(6) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.519(6) . ?
C3' H3' 1.0000 . ?
C4' C5' 1.511(6) . ?
C4' H4' 1.0000 . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
O1W H1W 0.8405 . ?
O1W H2W 0.8392 . ?
O1X H1X 0.8403 . ?
O1X H2X 0.8401 . ?
O2W H3W 0.8397 . ?
O2W H4W 0.8401 . ?

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
O11 P1 O12 117.78(18) . . ?
O11 P1 O13 106.73(17) . . ?
O12 P1 O13 110.81(17) . . ?
O11 P1 O5' 105.82(16) . . yes
O12 P1 O5' 109.98(17) . . yes
O13 P1 O5' 104.85(17) . . yes
P1 O13 H13 109.5 . . ?
C2' O2' H2O 109.5 . . ?
C3' O3' H3O 109.5 . . ?
C1' O4' C4' 110.2(3) . . ?
C5' O5' P1 118.8(3) . . ?
C6 N1 C2 120.6(3) . . ?
C6 N1 C1' 122.4(4) . . ?
C2 N1 C1' 116.4(3) . . ?
C4 N3 C2 125.1(4) . . ?
C4 N3 H3 117.5 . . ?
C2 N3 H3 117.5 . . ?
C4 N4 H41 120.0 . . ?
C4 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
O2 C2 N3 121.9(4) . . ?
O2 C2 N1 122.6(4) . . ?
N3 C2 N1 115.5(3) . . ?
N4 C4 N3 118.3(4) . . ?
N4 C4 C5 124.5(4) . . ?
N3 C4 C5 117.2(4) . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 N1 122.5(4) . . ?
C5 C6 H6 118.8 . . ?
N1 C6 H6 118.8 . . ?
O4' C1' N1 108.2(3) . . ?
O4' C1' C2' 107.1(3) . . ?
N1 C1' C2' 112.4(3) . . ?
O4' C1' H1' 109.7 . . ?
N1 C1' H1' 109.7 . . ?
C2' C1' H1' 109.7 . . ?
O2' C2' C3' 111.2(4) . . ?
O2' C2' C1' 104.4(3) . . ?
C3' C2' C1' 101.5(3) . . ?
O2' C2' H2' 113.0 . . ?
C3' C2' H2' 113.0 . . ?
C1' C2' H2' 113.0 . . ?
O3' C3' C4' 113.3(4) . . ?
O3' C3' C2' 111.2(4) . . ?
C4' C3' C2' 103.0(4) . . ?
O3' C3' H3' 109.7 . . ?
C4' C3' H3' 109.7 . . ?
C2' C3' H3' 109.7 . . ?
O4' C4' C5' 110.2(3) . . ?
O4' C4' C3' 105.3(3) . . ?
C5' C4' C3' 115.1(4) . . ?
O4' C4' H4' 108.7 . . ?
C5' C4' H4' 108.7 . . ?
C3' C4' H4' 108.7 . . ?
O5' C5' C4' 109.0(3) . . ?
O5' C5' H5'1 109.9 . . ?
C4' C5' H5'1 109.9 . . ?
O5' C5' H5'2 109.9 . . ?
C4' C5' H5'2 109.9 . . ?
H5'1 C5' H5'2 108.3 . . ?
H1W O1W H2W 108.1 . . ?
H1X O1X H2X 108.2 . . ?
H3W O2W H4W 108.0 . . ?

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
O11 P1 O5' C5' 176.0(3) . . . . ?
O12 P1 O5' C5' 47.8(3) . . . . ?
O13 P1 O5' C5' -71.4(3) . . . . ?
C4 N3 C2 O2 171.9(4) . . . . ?
C4 N3 C2 N1 -10.7(6) . . . . ?
C6 N1 C2 O2 -172.8(4) . . . . ?
C1' N1 C2 O2 -1.7(6) . . . . ?
C6 N1 C2 N3 9.7(6) . . . . ?
C1' N1 C2 N3 -179.1(4) . . . . ?
C2 N3 C4 N4 -175.0(4) . . . . ?
C2 N3 C4 C5 5.9(6) . . . . ?
N4 C4 C5 C6 -178.9(4) . . . . ?
N3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 N1 -0.6(6) . . . . ?
C2 N1 C6 C5 -4.7(6) . . . . ?
C1' N1 C6 C5 -175.3(4) . . . . ?
C4' O4' C1' N1 -109.4(4) . . . . ?
C4' O4' C1' C2' 12.0(4) . . . . ?
C6 N1 C1' O4' -5.9(5) . . . . ?
C2 N1 C1' O4' -176.9(3) . . . . yes
C6 N1 C1' C2' -124.0(4) . . . . ?
C2 N1 C1' C2' 65.0(5) . . . . ?
O4' C1' C2' O2' 85.9(4) . . . . ?
N1 C1' C2' O2' -155.4(4) . . . . ?
O4' C1' C2' C3' -29.7(4) . . . . ?
N1 C1' C2' C3' 89.0(4) . . . . ?
O2' C2' C3' O3' 46.4(5) . . . . ?
C1' C2' C3' O3' 156.9(3) . . . . ?
O2' C2' C3' C4' -75.3(4) . . . . ?
C1' C2' C3' C4' 35.3(4) . . . . ?
C1' O4' C4' C5' 135.8(3) . . . . ?
C1' O4' C4' C3' 11.1(4) . . . . ?
O3' C3' C4' O4' -149.5(3) . . . . ?
C2' C3' C4' O4' -29.3(4) . . . . ?
O3' C3' C4' C5' 88.9(4) . . . . ?
C2' C3' C4' C5' -150.9(4) . . . . ?
P1 O5' C5' C4' 151.6(3) . . . . ?
O4' C4' C5' O5' -68.8(4) . . . . ?
C3' C4' C5' O5' 50.1(5) . . . . ?

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

O13 H13 O11 0.84 1.79 2.612(4) 166.2 1_556
O2' H2O O3' 0.84 1.92 2.740(5) 165.8 2_655
O3' H3O O1W^a 0.84 1.80 2.60(2) 159.1 .
O3' H3O O1X^b 0.84 1.81 2.65(2) 176.5 .
O1W^a H2W^a O2 0.84 1.88 2.71(2) 165.9 1_655
O1X^b H2X^b O2 0.84 2.00 2.79(2) 156.6 1_655
O2W^a H3W^a O2' 0.84 1.91 2.733(9) 165.9 2_655
N3 H3 O12 0.88 1.80 2.625(5) 155.8 1_454
N4 H42 O11 0.88 1.91 2.779(5) 170.8 4_456
N4 H41 O12 0.88 2.14 2.869(5) 139.6 1_454
C6 H6 O13 0.95 2.53 3.364(5) 146.1 .
C6 H6 O5' 0.95 2.58 3.149(5) 118.8 .
C2' H2' O2 1.00 2.42 2.951(6) 112.3 .

_refine_diff_density_max         0.547
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_IV
_database_code_depnum_ccdc_archive 'CCDC 2385030'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P'
_chemical_formula_sum            'C9 H14 N3 O8 P'
_chemical_formula_weight         323.20

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           1
_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'

_cell_length_a                   4.7896(8)
_cell_length_b                   8.1312(14)
_cell_length_c                   8.4477(12)
_cell_angle_alpha                76.85(2)
_cell_angle_beta                 79.75(2)
_cell_angle_gamma                83.99(2)
_cell_volume                     314.55(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3035
_cell_measurement_theta_min      5.4390
_cell_measurement_theta_max      72.3270

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_F_000             168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    2.432
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            3810
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.447
_diffrn_reflns_theta_max         74.320
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.644
_diffrn_reflns_point_group_measured_fraction_full 0.664
_reflns_number_total             1640
_reflns_number_gt                1592
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.330
_reflns_Friedel_fraction_max     0.319
_reflns_Friedel_fraction_full    0.344

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1093P)²+0.0850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1640
_refine_ls_number_parameters     194
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.099
_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 0.68000(17) 0.83000(12) 0.70000(12) 0.0223(3) Uani 1 1 d . . . . .
O11 O 0.7640(7) 1.0063(4) 0.6859(4) 0.0248(7) Uani 1 1 d . . . . .
O12 O 0.4051(8) 0.7796(4) 0.8087(4) 0.0265(8) Uani 1 1 d . . . . .
O13 O 0.9273(8) 0.6964(4) 0.7573(5) 0.0280(8) Uani 1 1 d . . . . .
H13 H 1.072829 0.747119 0.754222 0.07(3) Uiso 1 1 calc R . . . .
O2 O 0.4123(8) 0.1783(5) 0.3687(5) 0.0296(8) Uani 1 1 d . . . . .
O2' O 0.8663(9) 0.4783(5) 0.0626(4) 0.0302(9) Uani 1 1 d . . . . .
H2O H 0.844595 0.554836 -0.020678 0.045 Uiso 1 1 calc R U . . .
O3' O 0.6226(9) 0.8193(5) 0.0785(5) 0.0307(8) Uani 1 1 d . . . . .
H3O H 0.534060 0.787774 0.014489 0.046 Uiso 1 1 calc R U . . .
O4' O 0.9594(7) 0.5288(4) 0.3844(4) 0.0254(7) Uani 1 1 d . . . . .
O5' O 0.6488(7) 0.7991(4) 0.5234(4) 0.0250(8) Uani 1 1 d . . . . .
N1 N 0.5687(9) 0.3612(5) 0.4985(5) 0.0235(8) Uani 1 1 d . . . . .
N3 N 0.1970(9) 0.1899(5) 0.6304(6) 0.0263(9) Uani 1 1 d . . . . .
H3 H 0.071318 0.120132 0.625943 0.032 Uiso 1 1 calc R U . . .
N4 N -0.0078(11) 0.1782(6) 0.8989(6) 0.0322(10) Uani 1 1 d . . . . .
H41 H -0.121083 0.104025 0.888676 0.039 Uiso 1 1 calc R U . . .
H42 H -0.021961 0.209739 0.993163 0.039 Uiso 1 1 calc R U . . .
C2 C 0.3950(11) 0.2384(6) 0.4912(6) 0.0252(10) Uani 1 1 d . . . . .
C4 C 0.1825(12) 0.2419(6) 0.7734(7) 0.0261(10) Uani 1 1 d . . . . .
C5 C 0.3718(12) 0.3626(7) 0.7784(7) 0.0281(11) Uani 1 1 d . . . . .
H5 H 0.367765 0.404524 0.875014 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5585(11) 0.4157(6) 0.6403(7) 0.0262(10) Uani 1 1 d . . . . .
H6 H 0.689099 0.495172 0.642408 0.031 Uiso 1 1 calc R U . . .
C1' C 0.7873(11) 0.4143(6) 0.3514(6) 0.0252(10) Uani 1 1 d . . . . .
H1' H 0.908271 0.312534 0.326582 0.030 Uiso 1 1 calc R U . . .
C2' C 0.6579(11) 0.5061(6) 0.1979(6) 0.0248(10) Uani 1 1 d . . . . .
H2' H 0.469728 0.464579 0.195476 0.030 Uiso 1 1 calc R U . . .
C3' C 0.6327(11) 0.6900(6) 0.2214(6) 0.0260(10) Uani 1 1 d . . . . .
H3' H 0.464134 0.706417 0.306422 0.031 Uiso 1 1 calc R U . . .
C4' C 0.9023(11) 0.6986(6) 0.2876(6) 0.0253(10) Uani 1 1 d . . . . .
H4' H 1.060846 0.723643 0.192991 0.030 Uiso 1 1 calc R U . . .
C5' C 0.8857(11) 0.8298(6) 0.3925(6) 0.0266(11) Uani 1 1 d . . . . .
H5'2 H 1.063873 0.821656 0.438622 0.032 Uiso 1 1 calc R U . . .
H5'1 H 0.860851 0.944931 0.324046 0.032 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 O12 1.502(4) . yes
P1 O11 1.502(3) . yes
P1 O13 1.585(4) . yes
P1 O5' 1.603(4) . yes
O13 H13 0.8400 . ?
O2 C2 1.227(6) . ?
O2' C2' 1.421(6) . ?
O2' H2O 0.8400 . ?
O3' C3' 1.413(6) . ?
O3' H3O 0.8400 . ?
O4' C1' 1.409(6) . ?
O4' C4' 1.462(6) . ?
O5' C5' 1.435(6) . ?
N1 C6 1.361(7) . ?
N1 C2 1.383(6) . ?
N1 C1' 1.488(6) . ?
N3 C4 1.357(7) . ?
N3 C2 1.381(7) . ?
N3 H3 0.8800 . ?
N4 C4 1.315(7) . ?
N4 H41 0.8800 . ?
N4 H42 0.8800 . ?
C4 C5 1.416(8) . ?
C5 C6 1.352(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1' C2' 1.540(7) . ?
C1' H1' 1.0000 . ?
C2' C3' 1.542(7) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.509(7) . ?
C3' H3' 1.0000 . ?
C4' C5' 1.521(7) . ?
C4' H4' 1.0000 . ?
C5' H5'2 0.9900 . ?
C5' H5'1 0.9900 . ?

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
O12 P1 O11 117.3(2) . . ?
O12 P1 O13 108.7(2) . . ?
O11 P1 O13 109.87(19) . . ?
O12 P1 O5' 104.9(2) . . yes
O11 P1 O5' 110.9(2) . . yes
O13 P1 O5' 104.27(19) . . yes
P1 O13 H13 109.5 . . ?
C2' O2' H2O 109.5 . . ?
C3' O3' H3O 109.5 . . ?
C1' O4' C4' 110.0(4) . . ?
C5' O5' P1 118.3(3) . . ?
C6 N1 C2 120.9(4) . . ?
C6 N1 C1' 122.1(4) . . ?
C2 N1 C1' 116.7(4) . . ?
C4 N3 C2 124.7(5) . . ?
C4 N3 H3 117.7 . . ?
C2 N3 H3 117.7 . . ?
C4 N4 H41 120.0 . . ?
C4 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
O2 C2 N3 122.2(5) . . ?
O2 C2 N1 122.4(5) . . ?
N3 C2 N1 115.4(4) . . ?
N4 C4 N3 118.1(5) . . ?
N4 C4 C5 123.8(5) . . ?
N3 C4 C5 118.1(5) . . ?
C6 C5 C4 117.4(5) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 N1 123.3(5) . . ?
C5 C6 H6 118.4 . . ?
N1 C6 H6 118.4 . . ?
O4' C1' N1 109.3(4) . . ?
O4' C1' C2' 106.7(4) . . ?
N1 C1' C2' 113.0(4) . . ?
O4' C1' H1' 109.3 . . ?
N1 C1' H1' 109.3 . . ?
C2' C1' H1' 109.3 . . ?
O2' C2' C1' 104.7(4) . . ?
O2' C2' C3' 113.3(4) . . ?
C1' C2' C3' 100.3(4) . . ?
O2' C2' H2' 112.6 . . ?
C1' C2' H2' 112.6 . . ?
C3' C2' H2' 112.6 . . ?
O3' C3' C4' 108.9(4) . . ?
O3' C3' C2' 116.6(4) . . ?
C4' C3' C2' 102.1(4) . . ?
O3' C3' H3' 109.6 . . ?
C4' C3' H3' 109.6 . . ?
C2' C3' H3' 109.6 . . ?
O4' C4' C3' 105.3(4) . . ?
O4' C4' C5' 110.4(4) . . ?
C3' C4' C5' 114.6(4) . . ?
O4' C4' H4' 108.8 . . ?
C3' C4' H4' 108.8 . . ?
C5' C4' H4' 108.8 . . ?
O5' C5' C4' 108.8(4) . . ?
O5' C5' H5'2 109.9 . . ?
C4' C5' H5'2 109.9 . . ?
O5' C5' H5'1 109.9 . . ?
C4' C5' H5'1 109.9 . . ?
H5'2 C5' H5'1 108.3 . . ?

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
O12 P1 O5' C5' -177.5(3) . . . . ?
O11 P1 O5' C5' 54.9(4) . . . . ?
O13 P1 O5' C5' -63.3(4) . . . . ?
C4 N3 C2 O2 174.6(5) . . . . ?
C4 N3 C2 N1 -6.4(7) . . . . ?
C6 N1 C2 O2 -175.0(5) . . . . ?
C1' N1 C2 O2 -1.9(7) . . . . ?
C6 N1 C2 N3 6.0(7) . . . . ?
C1' N1 C2 N3 179.1(4) . . . . ?
C2 N3 C4 N4 -176.4(5) . . . . ?
C2 N3 C4 C5 4.0(7) . . . . ?
N4 C4 C5 C6 179.3(5) . . . . ?
N3 C4 C5 C6 -1.1(7) . . . . ?
C4 C5 C6 N1 1.1(8) . . . . ?
C2 N1 C6 C5 -3.8(8) . . . . ?
C1' N1 C6 C5 -176.4(4) . . . . ?
C4' O4' C1' N1 -109.9(4) . . . . ?
C4' O4' C1' C2' 12.6(5) . . . . ?
C6 N1 C1' O4' -2.3(6) . . . . ?
C2 N1 C1' O4' -175.2(4) . . . . yes
C6 N1 C1' C2' -120.9(5) . . . . ?
C2 N1 C1' C2' 66.2(5) . . . . ?
O4' C1' C2' O2' 85.6(4) . . . . ?
N1 C1' C2' O2' -154.3(4) . . . . ?
O4' C1' C2' C3' -32.0(5) . . . . ?
N1 C1' C2' C3' 88.1(5) . . . . ?
O2' C2' C3' O3' 46.0(6) . . . . ?
C1' C2' C3' O3' 157.1(4) . . . . ?
O2' C2' C3' C4' -72.5(5) . . . . ?
C1' C2' C3' C4' 38.5(5) . . . . ?
C1' O4' C4' C3' 12.9(5) . . . . ?
C1' O4' C4' C5' 137.2(4) . . . . ?
O3' C3' C4' O4' -156.5(4) . . . . ?
C2' C3' C4' O4' -32.6(5) . . . . ?
O3' C3' C4' C5' 81.9(5) . . . . ?
C2' C3' C4' C5' -154.1(4) . . . . ?
P1 O5' C5' C4' 143.5(3) . . . . ?
O4' C4' C5' O5' -63.7(5) . . . . ?
C3' C4' C5' O5' 55.0(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

O13 H13 O12 0.84 1.79 2.588(5) 156.9 1_655
O2' H2O O13 0.84 1.96 2.764(5) 159.4 1_554
O3' H3O O12 0.84 1.96 2.763(5) 159.0 1_554
N3 H3 O11 0.88 1.76 2.595(6) 158.2 1_445
N4 H41 O11 0.88 2.22 2.924(6) 137.2 1_445
N4 H42 O2' 0.88 2.37 3.027(6) 131.4 1_456
C6 H6 O13 0.95 2.54 3.435(7) 158.0 .
C6 H6 O5' 0.95 2.45 3.100(6) 125.7 .

_refine_diff_density_max         0.561
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.081


_vrf_PLAT915_IV                  
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         32 %     
RESPONSE: Measured crystal was obtained by temperature-induced dehydration.
The absolute configuration of CMP is known.
;
####################################################################### 
# 
# 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_VI
_database_code_depnum_ccdc_archive 'CCDC 2385031'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P'
_chemical_formula_sum            'C9 H14 N3 O8 P'
_chemical_formula_weight         323.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.843(4)
_cell_length_b                   8.646(8)
_cell_length_c                   15.726(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.680(10)
_cell_angle_gamma                90
_cell_volume                     657.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1158
_cell_measurement_theta_min      0.0940
_cell_measurement_theta_max      0.8870

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.0251
_diffrn_radiation_type           'transmission electron microscope'
_diffrn_source                   'transmission electron microscope'
_diffrn_measurement_device_type  
'XtaLAB Synergy-ED, HyPix3000 fast, electron source at 200keV'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            3305
_diffrn_reflns_av_unetI/netI     0.1888
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         0.095
_diffrn_reflns_theta_max         0.899
_diffrn_reflns_theta_full        0.863
_diffrn_measured_fraction_theta_max 0.796
_diffrn_measured_fraction_theta_full 0.800
_diffrn_reflns_Laue_measured_fraction_max 0.796
_diffrn_reflns_Laue_measured_fraction_full 0.800
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 0.829
_reflns_number_total             2214
_reflns_number_gt                1583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_max     0.855
_reflns_Friedel_fraction_full    0.861

_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 1.171.41.80a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  "SHELXL-2019/2 (Sheldrick, 2019)')"
_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)+(0.1154P)²+0.2261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       8724(29)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
The absolute structure was determined based on the known absolute configuration of cytidine 5'-monophosphate
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     193
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.1322
_refine_ls_wR_factor_ref         0.3497
_refine_ls_wR_factor_gt          0.3358
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.109
_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 0.6472(16) 0.7750(8) 0.1516(6) 0.0216(19) Uani 1 1 d . . . . .
O11 O 0.902(3) 0.7552(15) 0.1031(11) 0.031(3) Uani 1 1 d . . . . .
O12 O 0.551(3) 0.9404(14) 0.1626(10) 0.027(3) Uani 1 1 d . U . . .
O13 O 0.416(3) 0.6738(17) 0.1011(11) 0.035(4) Uani 1 1 d . . . . .
H13 H 0.232188 0.715575 0.111153 0.053 Uiso 1 1 calc R U . . .
O2 O 1.017(3) 0.0721(17) 0.3329(11) 0.034(3) Uani 1 1 d . . . . .
O2' O 0.722(3) 0.3393(17) 0.4906(11) 0.035(3) Uani 1 1 d . . . . .
H2O H 0.831257 0.257440 0.520171 0.052 Uiso 1 1 calc R U . . .
O3' O 0.902(3) 0.6221(18) 0.4681(11) 0.032(3) Uani 1 1 d . . . . .
H3O H 0.859026 0.562083 0.518702 0.049 Uiso 1 1 calc R U . . .
O4' O 0.450(3) 0.4224(15) 0.3171(10) 0.027(3) Uani 1 1 d . . . . .
O5' O 0.704(3) 0.6944(16) 0.2415(11) 0.027(3) Uani 1 1 d . U . . .
N1 N 0.792(3) 0.2679(16) 0.2596(11) 0.025(2) Uani 1 1 d . . . . .
N3 N 1.116(3) 0.1169(16) 0.1973(11) 0.025(3) Uani 1 1 d . . . . .
H3 H 1.281171 0.042582 0.203601 0.030 Uiso 1 1 calc R U . . .
N4 N 1.222(3) 0.1365(15) 0.0571(11) 0.025(3) Uani 1 1 d . . . . .
H41 H 1.377226 0.059144 0.066592 0.030 Uiso 1 1 calc R U . . .
H42 H 1.181700 0.183958 -0.001136 0.030 Uiso 1 1 calc R U . . .
C2 C 0.984(3) 0.1363(18) 0.2693(13) 0.027(3) Uani 1 1 d . . . . .
C4 C 1.072(3) 0.1753(18) 0.1204(13) 0.026(3) Uani 1 1 d . . . . .
C5 C 0.860(3) 0.2977(16) 0.1129(12) 0.023(3) Uani 1 1 d . . . . .
H5 H 0.807542 0.356593 0.053265 0.028 Uiso 1 1 calc R U . . .
C6 C 0.737(4) 0.3315(18) 0.1845(13) 0.033(4) Uani 1 1 d . . . . .
H6 H 0.577667 0.419531 0.180039 0.039 Uiso 1 1 calc R U . . .
C1' C 0.646(3) 0.3067(17) 0.3365(12) 0.025(3) Uani 1 1 d . . . . .
H1' H 0.538742 0.204298 0.356389 0.030 Uiso 1 1 calc R U . . .
C2' C 0.824(4) 0.366(2) 0.4117(13) 0.031(3) Uani 1 1 d . . . . .
H2' H 1.031732 0.320312 0.410301 0.037 Uiso 1 1 calc R U . . .
C3' C 0.827(4) 0.5399(19) 0.3966(12) 0.026(3) Uani 1 1 d . U . . .
H3' H 0.968595 0.565737 0.348064 0.032 Uiso 1 1 calc R U . . .
C4' C 0.533(3) 0.5645(19) 0.3601(12) 0.026(3) Uani 1 1 d . . . . .
H4' H 0.402086 0.581684 0.412544 0.032 Uiso 1 1 calc R U . . .
C5' C 0.502(3) 0.7015(18) 0.3024(12) 0.028(3) Uani 1 1 d . . . . .
H5'2 H 0.295370 0.701960 0.270220 0.034 Uiso 1 1 calc R U . . .
H5'1 H 0.527229 0.807737 0.339489 0.034 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 O11 1.503(19) . yes
P1 O12 1.517(15) . yes
P1 O5' 1.584(17) . yes
P1 O13 1.592(14) . yes
O13 H13 0.9830 . ?
O2 C2 1.15(2) . ?
O2' C2' 1.38(3) . ?
O2' H2O 0.9830 . ?
O3' C3' 1.36(2) . ?
O3' H3O 0.9830 . ?
O4' C1' 1.401(19) . ?
O4' C4' 1.45(2) . ?
O5' C5' 1.41(3) . ?
N1 C6 1.32(2) . ?
N1 C2 1.47(2) . ?
N1 C1' 1.48(3) . ?
N3 C4 1.32(2) . ?
N3 C2 1.34(3) . ?
N3 H3 1.0270 . ?
N4 C4 1.31(3) . ?
N4 H41 1.0110 . ?
N4 H42 1.0110 . ?
C4 C5 1.47(2) . ?
C5 C6 1.34(3) . ?
C5 H5 1.0830 . ?
C6 H6 1.0830 . ?
C1' C2' 1.51(3) . ?
C1' H1' 1.0830 . ?
C2' C3' 1.52(2) . ?
C2' H2' 1.0830 . ?
C3' C4' 1.51(2) . ?
C3' H3' 1.0830 . ?
C4' C5' 1.49(2) . ?
C4' H4' 1.0830 . ?
C5' H5'2 1.0910 . ?
C5' H5'1 1.0910 . ?

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
O11 P1 O12 115.8(9) . . ?
O11 P1 O5' 107.6(9) . . yes
O12 P1 O5' 110.5(10) . . yes
O11 P1 O13 105.0(10) . . ?
O12 P1 O13 111.3(9) . . ?
O5' P1 O13 106.2(9) . . yes
P1 O13 H13 109.5 . . ?
C2' O2' H2O 109.5 . . ?
C3' O3' H3O 109.5 . . ?
C1' O4' C4' 109.9(12) . . ?
C5' O5' P1 119.8(11) . . ?
C6 N1 C2 120.4(17) . . ?
C6 N1 C1' 124.2(15) . . ?
C2 N1 C1' 115.0(14) . . ?
C4 N3 C2 132.0(16) . . ?
C4 N3 H3 114.0 . . ?
C2 N3 H3 114.0 . . ?
C4 N4 H41 120.0 . . ?
C4 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
O2 C2 N3 128.8(18) . . ?
O2 C2 N1 121(2) . . ?
N3 C2 N1 109.9(15) . . ?
N4 C4 N3 122.3(15) . . ?
N4 C4 C5 122.6(16) . . ?
N3 C4 C5 114.8(17) . . ?
C6 C5 C4 115.8(15) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
N1 C6 C5 126.1(16) . . ?
N1 C6 H6 117.0 . . ?
C5 C6 H6 117.0 . . ?
O4' C1' N1 109.7(14) . . ?
O4' C1' C2' 105.8(14) . . ?
N1 C1' C2' 116.2(14) . . ?
O4' C1' H1' 108.3 . . ?
N1 C1' H1' 108.3 . . ?
C2' C1' H1' 108.3 . . ?
O2' C2' C1' 115.2(16) . . ?
O2' C2' C3' 108.3(15) . . ?
C1' C2' C3' 103.0(13) . . ?
O2' C2' H2' 110.0 . . ?
C1' C2' H2' 110.0 . . ?
C3' C2' H2' 110.0 . . ?
O3' C3' C4' 115.9(16) . . ?
O3' C3' C2' 113.0(15) . . ?
C4' C3' C2' 100.4(13) . . ?
O3' C3' H3' 109.0 . . ?
C4' C3' H3' 109.0 . . ?
C2' C3' H3' 109.0 . . ?
O4' C4' C5' 112.0(15) . . ?
O4' C4' C3' 106.5(13) . . ?
C5' C4' C3' 113.5(15) . . ?
O4' C4' H4' 108.2 . . ?
C5' C4' H4' 108.2 . . ?
C3' C4' H4' 108.2 . . ?
O5' C5' C4' 109.2(14) . . ?
O5' C5' H5'2 109.8 . . ?
C4' C5' H5'2 109.8 . . ?
O5' C5' H5'1 109.8 . . ?
C4' C5' H5'1 109.8 . . ?
H5'2 C5' H5'1 108.3 . . ?

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
O11 P1 O5' C5' 177.1(12) . . . . ?
O12 P1 O5' C5' 49.8(15) . . . . ?
O13 P1 O5' C5' -70.9(15) . . . . ?
C4 N3 C2 O2 172.7(18) . . . . ?
C4 N3 C2 N1 -12(2) . . . . ?
C6 N1 C2 O2 -173.9(16) . . . . ?
C1' N1 C2 O2 -1(2) . . . . ?
C6 N1 C2 N3 11(2) . . . . ?
C1' N1 C2 N3 -176.6(12) . . . . ?
C2 N3 C4 N4 -177.6(16) . . . . ?
C2 N3 C4 C5 8(2) . . . . ?
N4 C4 C5 C6 -175.7(15) . . . . ?
N3 C4 C5 C6 -1(2) . . . . ?
C2 N1 C6 C5 -6(2) . . . . ?
C1' N1 C6 C5 -178.7(15) . . . . ?
C4 C5 C6 N1 1(2) . . . . ?
C4' O4' C1' N1 -111.7(15) . . . . ?
C4' O4' C1' C2' 14(2) . . . . ?
C6 N1 C1' O4' -1(2) . . . . ?
C2 N1 C1' O4' -174.0(12) . . . . yes
C6 N1 C1' C2' -121.3(17) . . . . ?
C2 N1 C1' C2' 66.1(17) . . . . ?
O4' C1' C2' O2' 84.9(18) . . . . ?
N1 C1' C2' O2' -153.1(14) . . . . ?
O4' C1' C2' C3' -32.8(19) . . . . ?
N1 C1' C2' C3' 89.2(16) . . . . ?
O2' C2' C3' O3' 38.6(19) . . . . ?
C1' C2' C3' O3' 161.1(17) . . . . ?
O2' C2' C3' C4' -85.5(17) . . . . ?
C1' C2' C3' C4' 37.0(19) . . . . ?
C1' O4' C4' C5' 134.6(17) . . . . ?
C1' O4' C4' C3' 10(2) . . . . ?
O3' C3' C4' O4' -151.4(16) . . . . ?
C2' C3' C4' O4' -29.3(19) . . . . ?
O3' C3' C4' C5' 85(2) . . . . ?
C2' C3' C4' C5' -153.1(16) . . . . ?
P1 O5' C5' C4' 153.4(11) . . . . yes
O4' C4' C5' O5' -70.5(17) . . . . yes
C3' C4' C5' O5' 50(2) . . . . yes

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

O13 H13 O11 0.98 1.63 2.59(2) 163.3 1_455
O2' H2O O3' 0.98 1.74 2.67(2) 154.9 2_746
O3' H3O O2 0.98 2.37 3.16(2) 136.3 2_756
O3' H3O O2' 0.98 2.08 2.63(2) 113.5 .
N3 H3 O12 1.03 1.73 2.69(2) 152.2 1_645
N4 H42 O11 1.01 1.74 2.75(2) 176.1 2_745
N4 H41 O12 1.01 1.97 2.798(19) 137.3 1_645
N4 H42 O13 1.01 2.58 3.15(3) 115.4 2_745
C6 H6 O13 1.08 2.62 3.55(2) 144.1 .

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.038


_vrf_PLAT029_VI                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.800 Why?  
RESPONSE: The low completeness is due to the measurement limitations of
the electron diffractometer associated with scanning a crystal with rather
low symmetry (monoclinic) in only one axis. It was decided not to merge
the data sets because, despite the increase in completeness, a decrease in
the overall quality of the model was observed, requiring, for example, the
use of additional constraints. The adopted structure should be treated as
only one of the possible models.
;
_vrf_PLAT340_VI                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02333 Ang.  
RESPONSE: Data collected using an electron diffractometer.
;
_vrf_PLAT911_VI                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        252 Report
RESPONSE: Data collected using an electron diffractometer.
;
_vrf_RINTA01_VI                  
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: Data collected using an electron diffractometer.
;
_vrf_PLAT020_VI                  
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.126 Report
RESPONSE: Data collected using an electron diffractometer.
;
_vrf_PLAT082_VI                  
;
PROBLEM: High R1 Value ..................................       0.13 Report
RESPONSE: Data collected using an electron diffractometer.
;
_vrf_PLAT084_VI                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.35 Report
RESPONSE: Data collected using an electron diffractometer.
;
####################################################################### 
# 
# 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_VIII
_database_code_depnum_ccdc_archive 'CCDC 2385034'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P, H2 O'
_chemical_formula_sum            'C9 H16 N3 O9 P'
_chemical_formula_weight         341.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           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                   8.367(2)
_cell_length_b                   34.158(7)
_cell_length_c                   4.8236(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1378.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6472
_cell_measurement_theta_min      2.5710
_cell_measurement_theta_max      74.5650

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    2.308
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            10019
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         75.563
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2682
_reflns_number_gt                2598
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.586
_reflns_Friedel_fraction_max     0.876
_reflns_Friedel_fraction_full    0.940

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1175P)²+3.7592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(19)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     201
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2112
_refine_ls_wR_factor_gt          0.2101
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.117
_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 0.7247(2) 0.17830(5) 0.8607(3) 0.0274(4) Uani 1 1 d . . . . .
O11 O 0.8904(6) 0.17418(15) 0.9682(10) 0.0327(11) Uani 1 1 d . . . . .
O12 O 0.7046(6) 0.20051(14) 0.5965(10) 0.0309(11) Uani 1 1 d . . . . .
O13 O 0.6137(6) 0.19800(15) 1.0829(9) 0.0322(11) Uani 1 1 d . . . . .
H13 H 0.649394 0.193362 1.242240 0.048 Uiso 1 1 calc R U . . .
O2 O 0.0067(6) 0.09729(15) 0.5212(13) 0.0388(13) Uani 1 1 d . . . . .
O2' O 0.2667(7) 0.02134(15) 0.8411(11) 0.0366(11) Uani 1 1 d . . . . .
H2O H 0.285432 0.022910 1.011764 0.055 Uiso 1 1 calc R U . . .
O3' O 0.5701(6) 0.03343(16) 0.5956(12) 0.0400(13) Uani 1 1 d . . . . .
H3O H 0.556846 0.014123 0.700975 0.060 Uiso 1 1 calc R U . . .
O4' O 0.3738(6) 0.09806(15) 1.0898(10) 0.0315(11) Uani 1 1 d . . . . .
O5' O 0.6474(6) 0.13641(15) 0.8057(10) 0.0322(11) Uani 1 1 d . . . . .
N1 N 0.2136(7) 0.12778(17) 0.7477(13) 0.0296(12) Uani 1 1 d . . . . .
N3 N 0.0643(7) 0.15976(17) 0.4070(13) 0.0315(13) Uani 1 1 d . . . . .
H3 H -0.001363 0.158444 0.264827 0.038 Uiso 1 1 calc R U . . .
N4 N 0.0948(8) 0.22471(17) 0.3032(13) 0.0318(13) Uani 1 1 d . . . . .
H41 H 0.023541 0.221945 0.170458 0.038 Uiso 1 1 calc R U . . .
H42 H 0.139309 0.247676 0.332709 0.038 Uiso 1 1 calc R U . . .
C2 C 0.0869(9) 0.1262(2) 0.5599(16) 0.0324(15) Uani 1 1 d . . . . .
C4 C 0.1348(9) 0.1944(2) 0.4580(16) 0.0322(15) Uani 1 1 d . . . . .
C5 C 0.2535(8) 0.1958(2) 0.6665(15) 0.0303(14) Uani 1 1 d . . . . .
H5 H 0.307698 0.219544 0.707534 0.036 Uiso 1 1 calc R U . . .
C6 C 0.2878(9) 0.1626(2) 0.8058(16) 0.0330(15) Uani 1 1 d . . . . .
H6 H 0.365836 0.163445 0.948695 0.040 Uiso 1 1 calc R U . . .
C1' C 0.2458(8) 0.0910(2) 0.9062(15) 0.0318(15) Uani 1 1 d . . . . .
H1' H 0.148440 0.082818 1.011561 0.038 Uiso 1 1 calc R U . . .
C2' C 0.3014(9) 0.05773(19) 0.7128(14) 0.0290(15) Uani 1 1 d . . . . .
H2' H 0.249670 0.059733 0.526460 0.035 Uiso 1 1 calc R U . . .
C3' C 0.4811(9) 0.0654(2) 0.6950(16) 0.0320(15) Uani 1 1 d . . . . .
H3' H 0.498855 0.088063 0.567628 0.038 Uiso 1 1 calc R U . . .
C4' C 0.5201(9) 0.0787(2) 0.9935(16) 0.0334(16) Uani 1 1 d . . . . .
H4' H 0.539982 0.055024 1.110741 0.040 Uiso 1 1 calc R U . . .
C5' C 0.6626(9) 0.1059(2) 1.0161(16) 0.0328(15) Uani 1 1 d . . . . .
H5'1 H 0.666080 0.117891 1.202961 0.039 Uiso 1 1 calc R U . . .
H5'2 H 0.762871 0.091084 0.987229 0.039 Uiso 1 1 calc R U . . .
O1W O 0.8644(18) 0.0301(4) 0.340(4) 0.055(5) Uiso 0.51(3) 1 d D . P A 1
H1W H 0.766349 0.026116 0.366762 0.082 Uiso 0.51(3) 1 d DR U P A 1
H2W H 0.884079 0.053566 0.379142 0.082 Uiso 0.51(3) 1 d DR U P A 1
O1X O 0.8911(17) 0.0224(4) 0.479(4) 0.045(5) Uiso 0.49(3) 1 d D . P A 2
H1X H 0.790969 0.022273 0.465918 0.068 Uiso 0.49(3) 1 d DR U P A 2
H2X H 0.923191 0.045313 0.450318 0.068 Uiso 0.49(3) 1 d DR U P A 2


_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 O11 1.487(5) . yes
P1 O12 1.492(5) . yes
P1 O13 1.570(5) . yes
P1 O5' 1.592(6) . yes
O13 H13 0.8400 . ?
O2 C2 1.209(9) . ?
O2' C2' 1.418(8) . ?
O2' H2O 0.8400 . ?
O3' C3' 1.405(9) . ?
O3' H3O 0.8400 . ?
O4' C1' 1.410(8) . ?
O4' C4' 1.467(9) . ?
O5' C5' 1.459(8) . ?
N1 C6 1.372(9) . ?
N1 C2 1.395(10) . ?
N1 C1' 1.496(9) . ?
N3 C4 1.346(9) . ?
N3 C2 1.375(9) . ?
N3 H3 0.8800 . ?
N4 C4 1.319(9) . ?
N4 H41 0.8800 . ?
N4 H42 0.8800 . ?
C4 C5 1.414(10) . ?
C5 C6 1.348(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C1' C2' 1.542(10) . ?
C1' H1' 1.0000 . ?
C2' C3' 1.528(10) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.545(10) . ?
C3' H3' 1.0000 . ?
C4' C5' 1.517(10) . ?
C4' H4' 1.0000 . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
O1W H1W 0.8419 . ?
O1W H2W 0.8386 . ?
O1X H1X 0.8397 . ?
O1X H2X 0.8396 . ?

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
O11 P1 O12 116.8(3) . . ?
O11 P1 O13 110.7(3) . . ?
O12 P1 O13 107.4(3) . . ?
O11 P1 O5' 110.6(3) . . yes
O12 P1 O5' 105.6(3) . . yes
O13 P1 O5' 105.0(3) . . yes
P1 O13 H13 109.5 . . ?
C2' O2' H2O 109.5 . . ?
C3' O3' H3O 109.5 . . ?
C1' O4' C4' 111.0(5) . . ?
C5' O5' P1 119.3(4) . . ?
C6 N1 C2 120.6(6) . . ?
C6 N1 C1' 122.9(6) . . ?
C2 N1 C1' 115.9(6) . . ?
C4 N3 C2 125.1(6) . . ?
C4 N3 H3 117.5 . . ?
C2 N3 H3 117.5 . . ?
C4 N4 H41 120.0 . . ?
C4 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
O2 C2 N3 121.4(7) . . ?
O2 C2 N1 123.6(7) . . ?
N3 C2 N1 114.9(6) . . ?
N4 C4 N3 118.4(7) . . ?
N4 C4 C5 123.7(7) . . ?
N3 C4 C5 117.8(6) . . ?
C6 C5 C4 118.4(7) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 N1 122.1(7) . . ?
C5 C6 H6 118.9 . . ?
N1 C6 H6 118.9 . . ?
O4' C1' N1 108.3(5) . . ?
O4' C1' C2' 106.1(6) . . ?
N1 C1' C2' 111.4(6) . . ?
O4' C1' H1' 110.3 . . ?
N1 C1' H1' 110.3 . . ?
C2' C1' H1' 110.3 . . ?
O2' C2' C3' 112.1(6) . . ?
O2' C2' C1' 108.7(6) . . ?
C3' C2' C1' 101.8(6) . . ?
O2' C2' H2' 111.3 . . ?
C3' C2' H2' 111.3 . . ?
C1' C2' H2' 111.3 . . ?
O3' C3' C2' 114.1(6) . . ?
O3' C3' C4' 115.7(6) . . ?
C2' C3' C4' 101.9(6) . . ?
O3' C3' H3' 108.3 . . ?
C2' C3' H3' 108.3 . . ?
C4' C3' H3' 108.3 . . ?
O4' C4' C5' 110.9(6) . . ?
O4' C4' C3' 104.5(6) . . ?
C5' C4' C3' 114.4(6) . . ?
O4' C4' H4' 108.9 . . ?
C5' C4' H4' 108.9 . . ?
C3' C4' H4' 108.9 . . ?
O5' C5' C4' 108.6(6) . . ?
O5' C5' H5'1 110.0 . . ?
C4' C5' H5'1 110.0 . . ?
O5' C5' H5'2 110.0 . . ?
C4' C5' H5'2 110.0 . . ?
H5'1 C5' H5'2 108.3 . . ?
H1W O1W H2W 108.2 . . ?
H1X O1X H2X 108.1 . . ?

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
O11 P1 O5' C5' 46.3(6) . . . . ?
O12 P1 O5' C5' 173.5(5) . . . . ?
O13 P1 O5' C5' -73.1(5) . . . . ?
C4 N3 C2 O2 171.8(7) . . . . ?
C4 N3 C2 N1 -11.7(10) . . . . ?
C6 N1 C2 O2 -172.3(7) . . . . ?
C1' N1 C2 O2 -0.6(11) . . . . ?
C6 N1 C2 N3 11.3(10) . . . . ?
C1' N1 C2 N3 -177.0(6) . . . . ?
C2 N3 C4 N4 -176.2(7) . . . . ?
C2 N3 C4 C5 6.8(11) . . . . ?
N4 C4 C5 C6 -177.9(7) . . . . ?
N3 C4 C5 C6 -1.0(10) . . . . ?
C4 C5 C6 N1 1.2(11) . . . . ?
C2 N1 C6 C5 -6.7(11) . . . . ?
C1' N1 C6 C5 -177.8(7) . . . . ?
C4' O4' C1' N1 -106.8(6) . . . . ?
C4' O4' C1' C2' 12.9(7) . . . . ?
C6 N1 C1' O4' -7.0(9) . . . . ?
C2 N1 C1' O4' -178.5(6) . . . . yes
C6 N1 C1' C2' -123.3(7) . . . . ?
C2 N1 C1' C2' 65.2(8) . . . . ?
O4' C1' C2' O2' 86.4(7) . . . . ?
N1 C1' C2' O2' -156.0(5) . . . . ?
O4' C1' C2' C3' -32.0(7) . . . . ?
N1 C1' C2' C3' 85.6(6) . . . . ?
O2' C2' C3' O3' 47.1(9) . . . . ?
C1' C2' C3' O3' 163.0(6) . . . . ?
O2' C2' C3' C4' -78.4(7) . . . . ?
C1' C2' C3' C4' 37.6(7) . . . . ?
C1' O4' C4' C5' 135.2(6) . . . . ?
C1' O4' C4' C3' 11.5(7) . . . . ?
O3' C3' C4' O4' -155.2(6) . . . . ?
C2' C3' C4' O4' -30.9(7) . . . . ?
O3' C3' C4' C5' 83.3(8) . . . . ?
C2' C3' C4' C5' -152.3(6) . . . . ?
P1 O5' C5' C4' 151.5(5) . . . . ?
O4' C4' C5' O5' -71.0(7) . . . . ?
C3' C4' C5' O5' 46.9(8) . . . . ?

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

O13 H13 O12 0.84 1.79 2.593(6) 160.3 1_556
O2' H2O O2' 0.84 2.24 2.832(5) 128.1 2
O3' H3O O1W^a 0.84 1.78 2.531(14) 147.8 2_655
O3' H3O O1X^b 0.84 1.88 2.674(15) 157.0 2_655
O1W^a H2W^a O2 0.84 1.94 2.728(15) 156.8 1_655
O1W^a H1W^a O3' 0.84 1.99 2.757(16) 150.1 .
O1X^b H2X^b O2 0.84 1.94 2.743(14) 160.3 1_655
O1X^b H1X^b O3' 0.84 1.99 2.770(14) 154.6 .
N3 H3 O11 0.88 1.78 2.615(8) 158.5 1_454
N4 H41 O11 0.88 2.20 2.918(8) 138.1 1_454
N4 H42 O12 0.88 1.88 2.757(8) 171.8 3_456
C6 H6 O13 0.95 2.47 3.268(9) 141.3 .
C6 H6 O5' 0.95 2.62 3.140(9) 114.6 .
C2' H2' O2 1.00 2.40 2.960(9) 114.3 .
C3' H3' O4' 1.00 2.55 3.252(9) 126.7 1_554
C4' H4' O3' 1.00 2.47 3.316(10) 142.7 1_556

_refine_diff_density_max         0.720
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.111


_vrf_PLAT340_VIII                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01033 Ang.  
RESPONSE: Measured crystal was obtained by temperature-induced dehydration.
;
####################################################################### 
# 
# 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_III
_database_code_depnum_ccdc_archive 'CCDC 2385029'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P, 0.5H2 O'
_chemical_formula_sum            'C9 H15 N3 O8.50 P'
_chemical_formula_weight         332.21

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           1
_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'

_cell_length_a                   4.7974(8)
_cell_length_b                   8.2932(10)
_cell_length_c                   16.861(3)
_cell_angle_alpha                101.48(2)
_cell_angle_beta                 92.04(2)
_cell_angle_gamma                95.55(2)
_cell_volume                     653.29(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4075
_cell_measurement_theta_min      2.6500
_cell_measurement_theta_max      74.3170

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             346
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.389
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            6382
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         75.645
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.573
_diffrn_reflns_point_group_measured_fraction_full 0.607
_reflns_number_total             3095
_reflns_number_gt                2725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.252
_reflns_Friedel_fraction_max     0.230
_reflns_Friedel_fraction_full    0.258

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0942P)²+3.1692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3095
_refine_ls_number_parameters     396
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2059
_refine_ls_wR_factor_gt          0.2016
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_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
P1A P 0.6345(4) -0.0988(3) 0.14479(17) 0.0294(6) Uani 1 1 d . . . . .
O11A O 0.7121(13) -0.2654(9) 0.1525(5) 0.0329(17) Uani 1 1 d . . . . .
O12A O 0.3768(13) -0.0960(9) 0.0905(4) 0.0295(16) Uani 1 1 d . . . . .
O13A O 0.8894(13) 0.0041(9) 0.1169(5) 0.0323(17) Uani 1 1 d . . . . .
H13A H 1.035579 -0.004781 0.143896 0.048 Uiso 1 1 calc R U . . .
O2A O 0.3015(15) 0.6917(9) 0.2919(5) 0.0358(17) Uani 1 1 d . . . . .
O2'A O 0.6930(15) 0.5336(10) 0.4468(5) 0.0372(17) Uani 1 1 d . . . . .
H2OA H 0.614635 0.531330 0.490373 0.056 Uiso 1 1 calc R U . . .
O3'A O 0.4161(18) 0.1997(10) 0.4432(5) 0.0421(19) Uani 1 1 d . . . . .
H3OA H 0.505876 0.258310 0.484210 0.063 Uiso 1 1 calc R U . . .
O4'A O 0.8491(14) 0.3382(9) 0.2911(5) 0.0325(16) Uani 1 1 d . . . . .
O5'A O 0.5722(14) 0.0092(9) 0.2297(4) 0.0329(16) Uani 1 1 d . . . . .
N1A N 0.4724(16) 0.4503(11) 0.2318(5) 0.0294(18) Uani 1 1 d . . . . .
N3A N 0.1342(16) 0.5640(11) 0.1650(6) 0.0309(19) Uani 1 1 d . . . . .
H3A H 0.009286 0.635333 0.165981 0.037 Uiso 1 1 calc R U . . .
N4A N -0.0346(19) 0.4576(12) 0.0334(6) 0.040(2) Uani 1 1 d . . . . .
H41A H -0.149476 0.535001 0.037055 0.048 Uiso 1 1 calc R U . . .
H42A H -0.032961 0.383755 -0.011888 0.048 Uiso 1 1 calc R U . . .
C2A C 0.303(2) 0.5799(13) 0.2333(6) 0.034(2) Uani 1 1 d . . . . .
C4A C 0.1390(19) 0.4523(13) 0.0973(6) 0.029(2) Uani 1 1 d . . . . .
C5A C 0.325(2) 0.3271(13) 0.0958(7) 0.035(2) Uani 1 1 d . . . . .
H5A H 0.336141 0.243115 0.049064 0.042 Uiso 1 1 calc R U . . .
C6A C 0.480(2) 0.3347(13) 0.1635(7) 0.032(2) Uani 1 1 d . . . . .
H6A H 0.605298 0.252914 0.163823 0.038 Uiso 1 1 calc R U . . .
C1'A C 0.6679(19) 0.4690(13) 0.3059(7) 0.029(2) Uani 1 1 d . . . . .
H1'A H 0.781761 0.579406 0.316329 0.035 Uiso 1 1 calc R U . . .
C2'A C 0.5088(19) 0.4472(12) 0.3800(6) 0.027(2) Uani 1 1 d . . . . .
H2'A H 0.320125 0.488978 0.380126 0.033 Uiso 1 1 calc R U . . .
C3'A C 0.493(2) 0.2610(14) 0.3728(6) 0.033(2) Uani 1 1 d . . . . .
H3'A H 0.348241 0.209835 0.328493 0.039 Uiso 1 1 calc R U . . .
C4'A C 0.771(2) 0.2168(13) 0.3430(6) 0.032(2) Uani 1 1 d . . . . .
H4'A H 0.910583 0.236405 0.390418 0.038 Uiso 1 1 calc R U . . .
C5'A C 0.778(2) 0.0431(14) 0.2957(6) 0.035(2) Uani 1 1 d . . . . .
H5'2 H 0.966739 0.030088 0.274695 0.042 Uiso 1 1 calc R U . . .
H5'1 H 0.740787 -0.036530 0.331642 0.042 Uiso 1 1 calc R U . . .
P1B P 0.7866(5) 0.4808(3) 0.64589(17) 0.0304(6) Uani 1 1 d . . . . .
O11B O 0.8763(15) 0.3186(9) 0.6566(5) 0.0360(17) Uani 1 1 d . . . . .
O12B O 0.5260(14) 0.4766(9) 0.5924(4) 0.0334(16) Uani 1 1 d . . . . .
O13B O 1.0271(16) 0.5899(9) 0.6154(5) 0.0372(18) Uani 1 1 d . . . . .
H13B H 1.179246 0.549062 0.619595 0.056 Uiso 1 1 calc R U . . .
O2B O 0.4925(16) 1.2705(10) 0.8243(5) 0.0387(19) Uani 1 1 d . . . . .
O2'B O 0.8835(17) 1.0855(10) 0.9666(5) 0.0380(18) Uani 1 1 d . . . . .
H2OB H 0.841849 1.047493 1.007744 0.057 Uiso 1 1 calc R U . . .
O3'B O 0.6329(16) 0.7485(10) 0.9565(5) 0.0364(17) Uani 1 1 d . . . . .
H3OB H 0.605155 0.823897 0.995833 0.055 Uiso 1 1 calc R U . . .
O4'B O 1.0188(14) 0.9057(9) 0.8063(4) 0.0324(16) Uani 1 1 d . . . . .
O5'B O 0.7242(14) 0.5884(9) 0.7330(4) 0.0333(17) Uani 1 1 d . . . . .
N1B N 0.6525(18) 1.0344(10) 0.7547(5) 0.0309(19) Uani 1 1 d . . . . .
N3B N 0.3010(19) 1.1575(11) 0.6970(6) 0.034(2) Uani 1 1 d . . . . .
H3B H 0.177016 1.229934 0.701660 0.040 Uiso 1 1 calc R U . . .
N4B N 0.1258(19) 1.0653(11) 0.5672(6) 0.036(2) Uani 1 1 d . . . . .
H41B H 0.012128 1.143527 0.575087 0.043 Uiso 1 1 calc R U . . .
H42B H 0.121278 0.997015 0.519938 0.043 Uiso 1 1 calc R U . . .
C2B C 0.479(2) 1.1626(13) 0.7631(7) 0.032(2) Uani 1 1 d . . . . .
C4B C 0.300(2) 1.0508(13) 0.6256(7) 0.034(2) Uani 1 1 d . . . . .
C5B C 0.481(2) 0.9242(13) 0.6187(7) 0.032(2) Uani 1 1 d . . . . .
H5B H 0.478474 0.842132 0.570418 0.039 Uiso 1 1 calc R U . . .
C6B C 0.658(2) 0.9240(14) 0.6834(7) 0.035(2) Uani 1 1 d . . . . .
H6B H 0.790084 0.844594 0.678792 0.042 Uiso 1 1 calc R U . . .
C1'B C 0.849(2) 1.0330(13) 0.8255(7) 0.032(2) Uani 1 1 d . . . . .
H1'B H 0.970697 1.140961 0.839049 0.038 Uiso 1 1 calc R U . . .
C2'B C 0.698(2) 1.0059(12) 0.9001(6) 0.030(2) Uani 1 1 d . . . . .
H2'B H 0.512011 1.051361 0.902489 0.036 Uiso 1 1 calc R U . . .
C3'B C 0.666(2) 0.8152(14) 0.8868(6) 0.032(2) Uani 1 1 d . . . . .
H3'B H 0.508356 0.767955 0.845910 0.039 Uiso 1 1 calc R U . . .
C4'B C 0.946(2) 0.7761(14) 0.8508(6) 0.032(2) Uani 1 1 d . . . . .
H4'B H 1.089963 0.785631 0.896215 0.038 Uiso 1 1 calc R U . . .
C5'B C 0.939(2) 0.6083(15) 0.7975(6) 0.034(2) Uani 1 1 d . . . . .
H5'4 H 1.124037 0.594939 0.774191 0.041 Uiso 1 1 calc R U . . .
H5'3 H 0.900248 0.522231 0.829937 0.041 Uiso 1 1 calc R U . . .
O1W O 0.083(3) 0.8036(13) 0.4391(7) 0.070(3) Uani 1 1 d DG . . . .
H2W H 0.122538 0.760296 0.391967 0.106 Uiso 1 1 d DG U . . .
H1W H 0.027918 0.727279 0.462749 0.106 Uiso 1 1 d DG 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
P1A O11A 1.494(7) . yes
P1A O12A 1.517(7) . yes
P1A O13A 1.564(7) . yes
P1A O5'A 1.586(8) . yes
O13A H13A 0.8400 . ?
O2A C2A 1.215(13) . ?
O2'A C2'A 1.430(12) . ?
O2'A H2OA 0.8400 . ?
O3'A C3'A 1.427(13) . ?
O3'A H3OA 0.8400 . ?
O4'A C1'A 1.444(12) . ?
O4'A C4'A 1.490(12) . ?
O5'A C5'A 1.428(12) . ?
N1A C6A 1.347(14) . ?
N1A C2A 1.405(13) . ?
N1A C1'A 1.508(13) . ?
N3A C4A 1.321(14) . ?
N3A C2A 1.361(13) . ?
N3A H3A 0.8800 . ?
N4A C4A 1.348(13) . ?
N4A H41A 0.8800 . ?
N4A H42A 0.8800 . ?
C4A C5A 1.429(14) . ?
C5A C6A 1.328(15) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C1'A C2'A 1.520(14) . ?
C1'A H1'A 1.0000 . ?
C2'A C3'A 1.520(14) . ?
C2'A H2'A 1.0000 . ?
C3'A C4'A 1.497(15) . ?
C3'A H3'A 1.0000 . ?
C4'A C5'A 1.505(15) . ?
C4'A H4'A 1.0000 . ?
C5'A H5'2 0.9900 . ?
C5'A H5'1 0.9900 . ?
P1B O11B 1.493(8) . yes
P1B O12B 1.509(7) . yes
P1B O13B 1.562(8) . yes
P1B O5'B 1.614(8) . yes
O13B H13B 0.8400 . ?
O2B C2B 1.218(13) . ?
O2'B C2'B 1.417(12) . ?
O2'B H2OB 0.8400 . ?
O3'B C3'B 1.403(13) . ?
O3'B H3OB 0.8400 . ?
O4'B C1'B 1.389(12) . ?
O4'B C4'B 1.452(13) . ?
O5'B C5'B 1.445(11) . ?
N1B C6B 1.360(13) . ?
N1B C2B 1.400(13) . ?
N1B C1'B 1.498(13) . ?
N3B C4B 1.344(14) . ?
N3B C2B 1.373(13) . ?
N3B H3B 0.8800 . ?
N4B C4B 1.302(14) . ?
N4B H41B 0.8800 . ?
N4B H42B 0.8800 . ?
C4B C5B 1.414(15) . ?
C5B C6B 1.361(15) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C1'B C2'B 1.520(15) . ?
C1'B H1'B 1.0000 . ?
C2'B C3'B 1.544(14) . ?
C2'B H2'B 1.0000 . ?
C3'B C4'B 1.527(14) . ?
C3'B H3'B 1.0000 . ?
C4'B C5'B 1.495(15) . ?
C4'B H4'B 1.0000 . ?
C5'B H5'4 0.9900 . ?
C5'B H5'3 0.9900 . ?
O1W H2W 0.8402 . ?
O1W H1W 0.8400 . ?

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
O11A P1A O12A 116.5(4) . . ?
O11A P1A O13A 110.1(4) . . ?
O12A P1A O13A 109.3(4) . . ?
O11A P1A O5'A 111.9(4) . . yes
O12A P1A O5'A 104.5(4) . . yes
O13A P1A O5'A 103.6(4) . . yes
P1A O13A H13A 109.5 . . ?
C2'A O2'A H2OA 109.5 . . ?
C3'A O3'A H3OA 109.5 . . ?
C1'A O4'A C4'A 109.1(7) . . ?
C5'A O5'A P1A 120.7(7) . . ?
C6A N1A C2A 120.1(8) . . ?
C6A N1A C1'A 124.7(8) . . ?
C2A N1A C1'A 114.6(8) . . ?
C4A N3A C2A 126.5(9) . . ?
C4A N3A H3A 116.7 . . ?
C2A N3A H3A 116.7 . . ?
C4A N4A H41A 120.0 . . ?
C4A N4A H42A 120.0 . . ?
H41A N4A H42A 120.0 . . ?
O2A C2A N3A 123.6(11) . . ?
O2A C2A N1A 122.4(10) . . ?
N3A C2A N1A 113.9(9) . . ?
N3A C4A N4A 119.3(9) . . ?
N3A C4A C5A 118.1(9) . . ?
N4A C4A C5A 122.6(10) . . ?
C6A C5A C4A 116.3(10) . . ?
C6A C5A H5A 121.9 . . ?
C4A C5A H5A 121.9 . . ?
C5A C6A N1A 124.7(10) . . ?
C5A C6A H6A 117.7 . . ?
N1A C6A H6A 117.7 . . ?
O4'A C1'A N1A 107.9(8) . . ?
O4'A C1'A C2'A 106.6(8) . . ?
N1A C1'A C2'A 111.6(8) . . ?
O4'A C1'A H1'A 110.2 . . ?
N1A C1'A H1'A 110.2 . . ?
C2'A C1'A H1'A 110.2 . . ?
O2'A C2'A C3'A 111.7(8) . . ?
O2'A C2'A C1'A 104.0(8) . . ?
C3'A C2'A C1'A 101.2(8) . . ?
O2'A C2'A H2'A 113.0 . . ?
C3'A C2'A H2'A 113.0 . . ?
C1'A C2'A H2'A 113.0 . . ?
O3'A C3'A C4'A 114.2(9) . . ?
O3'A C3'A C2'A 116.4(9) . . ?
C4'A C3'A C2'A 104.3(8) . . ?
O3'A C3'A H3'A 107.1 . . ?
C4'A C3'A H3'A 107.1 . . ?
C2'A C3'A H3'A 107.1 . . ?
O4'A C4'A C3'A 103.9(8) . . ?
O4'A C4'A C5'A 110.1(9) . . ?
C3'A C4'A C5'A 116.2(9) . . ?
O4'A C4'A H4'A 108.8 . . ?
C3'A C4'A H4'A 108.8 . . ?
C5'A C4'A H4'A 108.8 . . ?
O5'A C5'A C4'A 109.9(8) . . ?
O5'A C5'A H5'2 109.7 . . ?
C4'A C5'A H5'2 109.7 . . ?
O5'A C5'A H5'1 109.7 . . ?
C4'A C5'A H5'1 109.7 . . ?
H5'2 C5'A H5'1 108.2 . . ?
O11B P1B O12B 117.3(4) . . ?
O11B P1B O13B 111.9(4) . . ?
O12B P1B O13B 107.9(4) . . ?
O11B P1B O5'B 109.4(4) . . yes
O12B P1B O5'B 105.5(4) . . yes
O13B P1B O5'B 103.9(4) . . yes
P1B O13B H13B 109.5 . . ?
C2'B O2'B H2OB 109.5 . . ?
C3'B O3'B H3OB 109.5 . . ?
C1'B O4'B C4'B 110.9(8) . . ?
C5'B O5'B P1B 117.3(6) . . ?
C6B N1B C2B 121.7(9) . . ?
C6B N1B C1'B 121.3(8) . . ?
C2B N1B C1'B 116.8(8) . . ?
C4B N3B C2B 125.2(10) . . ?
C4B N3B H3B 117.4 . . ?
C2B N3B H3B 117.4 . . ?
C4B N4B H41B 120.0 . . ?
C4B N4B H42B 120.0 . . ?
H41B N4B H42B 120.0 . . ?
O2B C2B N3B 123.6(10) . . ?
O2B C2B N1B 121.8(9) . . ?
N3B C2B N1B 114.6(9) . . ?
N4B C4B N3B 118.2(10) . . ?
N4B C4B C5B 123.2(10) . . ?
N3B C4B C5B 118.5(10) . . ?
C6B C5B C4B 117.7(10) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?
N1B C6B C5B 121.8(10) . . ?
N1B C6B H6B 119.1 . . ?
C5B C6B H6B 119.1 . . ?
O4'B C1'B N1B 110.2(8) . . ?
O4'B C1'B C2'B 106.8(8) . . ?
N1B C1'B C2'B 112.8(9) . . ?
O4'B C1'B H1'B 109.0 . . ?
N1B C1'B H1'B 109.0 . . ?
C2'B C1'B H1'B 109.0 . . ?
O2'B C2'B C1'B 104.9(9) . . ?
O2'B C2'B C3'B 114.0(8) . . ?
C1'B C2'B C3'B 101.2(8) . . ?
O2'B C2'B H2'B 112.0 . . ?
C1'B C2'B H2'B 112.0 . . ?
C3'B C2'B H2'B 112.0 . . ?
O3'B C3'B C4'B 110.0(8) . . ?
O3'B C3'B C2'B 116.1(9) . . ?
C4'B C3'B C2'B 101.0(8) . . ?
O3'B C3'B H3'B 109.8 . . ?
C4'B C3'B H3'B 109.8 . . ?
C2'B C3'B H3'B 109.8 . . ?
O4'B C4'B C5'B 111.2(9) . . ?
O4'B C4'B C3'B 105.0(8) . . ?
C5'B C4'B C3'B 114.6(9) . . ?
O4'B C4'B H4'B 108.6 . . ?
C5'B C4'B H4'B 108.6 . . ?
C3'B C4'B H4'B 108.6 . . ?
O5'B C5'B C4'B 109.9(8) . . ?
O5'B C5'B H5'4 109.7 . . ?
C4'B C5'B H5'4 109.7 . . ?
O5'B C5'B H5'3 109.7 . . ?
C4'B C5'B H5'3 109.7 . . ?
H5'4 C5'B H5'3 108.2 . . ?
H2W O1W H1W 108.1 . . ?

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
O11A P1A O5'A C5'A 56.9(8) . . . . ?
O12A P1A O5'A C5'A -176.2(7) . . . . ?
O13A P1A O5'A C5'A -61.7(8) . . . . ?
C4A N3A C2A O2A 175.1(10) . . . . ?
C4A N3A C2A N1A -7.8(15) . . . . ?
C6A N1A C2A O2A -175.9(10) . . . . ?
C1'A N1A C2A O2A -4.9(15) . . . . ?
C6A N1A C2A N3A 7.0(14) . . . . ?
C1'A N1A C2A N3A 178.0(8) . . . . ?
C2A N3A C4A N4A -177.0(10) . . . . ?
C2A N3A C4A C5A 4.7(15) . . . . ?
N3A C4A C5A C6A -0.4(15) . . . . ?
N4A C4A C5A C6A -178.7(10) . . . . ?
C4A C5A C6A N1A 0.2(16) . . . . ?
C2A N1A C6A C5A -3.8(15) . . . . ?
C1'A N1A C6A C5A -173.8(10) . . . . ?
C4'A O4'A C1'A N1A -109.3(8) . . . . ?
C4'A O4'A C1'A C2'A 10.7(10) . . . . ?
C6A N1A C1'A O4'A -2.7(13) . . . . ?
C2A N1A C1'A O4'A -173.2(8) . . . . yes
C6A N1A C1'A C2'A -119.5(10) . . . . ?
C2A N1A C1'A C2'A 70.0(11) . . . . ?
O4'A C1'A C2'A O2'A 85.9(9) . . . . ?
N1A C1'A C2'A O2'A -156.6(8) . . . . ?
O4'A C1'A C2'A C3'A -30.1(9) . . . . ?
N1A C1'A C2'A C3'A 87.5(9) . . . . ?
O2'A C2'A C3'A O3'A 55.1(11) . . . . ?
C1'A C2'A C3'A O3'A 165.3(9) . . . . ?
O2'A C2'A C3'A C4'A -71.8(10) . . . . ?
C1'A C2'A C3'A C4'A 38.4(9) . . . . ?
C1'A O4'A C4'A C3'A 13.7(10) . . . . ?
C1'A O4'A C4'A C5'A 138.8(9) . . . . ?
O3'A C3'A C4'A O4'A -160.8(9) . . . . ?
C2'A C3'A C4'A O4'A -32.6(10) . . . . ?
O3'A C3'A C4'A C5'A 78.1(12) . . . . ?
C2'A C3'A C4'A C5'A -153.7(9) . . . . ?
P1A O5'A C5'A C4'A 142.4(8) . . . . ?
O4'A C4'A C5'A O5'A -63.6(11) . . . . ?
C3'A C4'A C5'A O5'A 54.2(12) . . . . ?
O11B P1B O5'B C5'B 51.1(9) . . . . ?
O12B P1B O5'B C5'B 178.2(8) . . . . ?
O13B P1B O5'B C5'B -68.5(8) . . . . ?
C4B N3B C2B O2B 172.8(10) . . . . ?
C4B N3B C2B N1B -6.0(15) . . . . ?
C6B N1B C2B O2B -173.0(10) . . . . ?
C1'B N1B C2B O2B 1.8(14) . . . . ?
C6B N1B C2B N3B 5.7(14) . . . . ?
C1'B N1B C2B N3B -179.4(9) . . . . ?
C2B N3B C4B N4B -177.3(10) . . . . ?
C2B N3B C4B C5B 5.3(16) . . . . ?
N4B C4B C5B C6B 178.7(11) . . . . ?
N3B C4B C5B C6B -4.0(15) . . . . ?
C2B N1B C6B C5B -5.3(16) . . . . ?
C1'B N1B C6B C5B -179.9(10) . . . . ?
C4B C5B C6B N1B 4.2(16) . . . . ?
C4'B O4'B C1'B N1B -110.0(9) . . . . ?
C4'B O4'B C1'B C2'B 12.9(11) . . . . ?
C6B N1B C1'B O4'B -1.4(13) . . . . ?
C2B N1B C1'B O4'B -176.3(9) . . . . yes
C6B N1B C1'B C2'B -120.7(10) . . . . ?
C2B N1B C1'B C2'B 64.5(12) . . . . ?
O4'B C1'B C2'B O2'B 86.7(10) . . . . ?
N1B C1'B C2'B O2'B -152.1(8) . . . . ?
O4'B C1'B C2'B C3'B -32.1(10) . . . . ?
N1B C1'B C2'B C3'B 89.0(9) . . . . ?
O2'B C2'B C3'B O3'B 44.6(12) . . . . ?
C1'B C2'B C3'B O3'B 156.6(8) . . . . ?
O2'B C2'B C3'B C4'B -74.2(10) . . . . ?
C1'B C2'B C3'B C4'B 37.8(9) . . . . ?
C1'B O4'B C4'B C5'B 136.9(9) . . . . ?
C1'B O4'B C4'B C3'B 12.3(11) . . . . ?
O3'B C3'B C4'B O4'B -154.6(8) . . . . ?
C2'B C3'B C4'B O4'B -31.4(10) . . . . ?
O3'B C3'B C4'B C5'B 83.1(11) . . . . ?
C2'B C3'B C4'B C5'B -153.8(9) . . . . ?
P1B O5'B C5'B C4'B 145.2(8) . . . . ?
O4'B C4'B C5'B O5'B -62.8(11) . . . . ?
C3'B C4'B C5'B O5'B 56.1(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

O13A H13A O12A 0.84 2.03 2.580(9) 122.1 1_655
O2'A H2OA O12B 0.84 1.92 2.724(11) 161.1 .
O3'A H3OA O12B 0.84 2.29 3.042(11) 148.9 .
O13B H13B O12B 0.84 1.86 2.668(11) 159.5 1_655
O2'B H2OB O13A 0.84 1.95 2.749(11) 157.6 1_566
O3'B H3OB O12A 0.84 2.01 2.761(10) 148.7 1_566
O3'B H3OB O13A 0.84 2.54 3.209(12) 137.3 1_566
O1W H1W O2'A 0.84 2.13 2.803(12) 137.1 1_455
O1W H2W O2A 0.84 1.93 2.751(13) 165.9 .
N3A H3A O11A 0.88 1.74 2.605(10) 165.6 1_465
N3B H3B O11B 0.88 1.88 2.681(11) 149.8 1_465
N4A H41A O11A 0.88 2.45 3.108(12) 132.2 1_465
N4A H42A O2'B 0.88 2.42 3.049(12) 128.9 1_444
N4B H41B O11B 0.88 1.97 2.733(12) 144.5 1_465
N4B H42B O1W 0.88 1.88 2.728(14) 162.2 .
C5A H5A O2'B 0.95 2.62 3.218(13) 121.2 1_444
C6A H6A O13A 0.95 2.59 3.506(13) 161.8 .
C6A H6A O5'A 0.95 2.49 3.182(12) 129.9 .
C2'A H2'A O2A 1.00 2.46 2.965(12) 110.6 .
C6B H6B O13B 0.95 2.56 3.457(14) 157.7 .
C6B H6B O5'B 0.95 2.47 3.102(13) 123.7 .
C2'B H2'B O2B 1.00 2.46 2.978(13) 112.0 .

_refine_diff_density_max         0.903
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.112


_vrf_PLAT029_III                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.957 Why?  
RESPONSE: This is a triclinic, non-centrosymmetric crystal obtained by
temperature-induced dehydration. 
;
_vrf_PLAT340_III                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01492 Ang.  
RESPONSE: Measured crystal was obtained by temperature-induced dehydration.
;
_vrf_PLAT915_III                 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         23 %     
RESPONSE: Measured crystal was obtained by temperature-induced dehydration.
The absolute configuration of CMP is known.
;
####################################################################### 
# 
# 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_VII_LT
_database_code_depnum_ccdc_archive 'CCDC 2385032'
loop_
_audit_author_name
_audit_author_address
'Oskar Kaszubowski Katarzyna Slepokura Jakub Wojciechowski'
;University of Wroclaw
Poland
;
_audit_update_record             
;
2024-11-21 deposited with the CCDC.	2025-01-28 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         'C9 H14 N3 O8 P, 1.5H2 O'
_chemical_formula_sum            'C9 H17 N3 O9.50 P'
_chemical_formula_weight         350.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           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                   8.4220(14)
_cell_length_b                   35.163(6)
_cell_length_c                   9.693(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2870.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8868
_cell_measurement_theta_min      2.4760
_cell_measurement_theta_max      75.2940

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    2.259
_shelx_estimated_absorpt_T_min   0.743
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            19770
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.513
_diffrn_reflns_theta_max         75.627
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             5485
_reflns_number_gt                4917
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_max     0.838
_reflns_Friedel_fraction_full    0.917

_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT-2019 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0835P)²+1.3972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00061(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5485
_refine_ls_number_parameters     422
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.274
_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
P1A P 0.55539(11) 0.17948(3) 0.19509(9) 0.0182(2) Uani 1 1 d . . . . .
O11A O 0.5400(3) 0.19959(7) 0.0601(3) 0.0229(6) Uani 1 1 d . . . . .
O12A O 0.7196(3) 0.17374(8) 0.2500(3) 0.0233(6) Uani 1 1 d . . . . .
O13A O 0.4498(3) 0.20180(8) 0.3024(3) 0.0240(6) Uani 1 1 d . . . . .
H13A H 0.483981 0.197793 0.382537 0.036 Uiso 1 1 calc R U . . .
O2A O -0.1673(3) 0.10488(8) 0.0349(3) 0.0261(6) Uani 1 1 d . . . . .
O2'A O 0.0664(3) 0.03494(7) 0.2439(3) 0.0281(6) Uani 1 1 d . . . . .
H2OA H 0.084268 0.014016 0.205122 0.042 Uiso 1 1 calc R U . . .
O3'A O 0.3645(3) 0.03476(7) 0.1191(3) 0.0249(6) Uani 1 1 d . . . . .
H3OA H 0.450172 0.038430 0.076705 0.037 Uiso 1 1 calc R U . . .
O4'A O 0.1916(3) 0.10916(7) 0.3242(3) 0.0218(6) Uani 1 1 d . . . . .
O5'A O 0.4686(3) 0.13944(7) 0.1755(3) 0.0220(6) Uani 1 1 d . . . . .
N1A N 0.0397(4) 0.13503(9) 0.1423(3) 0.0207(7) Uani 1 1 d . . . . .
N3A N -0.1016(4) 0.16427(9) -0.0345(3) 0.0207(7) Uani 1 1 d . . . . .
H3A H -0.167393 0.162093 -0.104646 0.025 Uiso 1 1 calc R U . . .
N4A N -0.0664(4) 0.22642(9) -0.0988(4) 0.0242(7) Uani 1 1 d . . . . .
H41A H -0.139302 0.223175 -0.162771 0.029 Uiso 1 1 calc R U . . .
H42A H -0.019586 0.248646 -0.089497 0.029 Uiso 1 1 calc R U . . .
C2A C -0.0828(4) 0.13315(11) 0.0481(4) 0.0219(8) Uani 1 1 d . . . . .
C4A C -0.0276(5) 0.19829(11) -0.0180(4) 0.0204(8) Uani 1 1 d . . . . .
C5A C 0.0890(5) 0.20022(11) 0.0882(4) 0.0215(8) Uani 1 1 d . . . . .
H5A H 0.145256 0.223157 0.105499 0.026 Uiso 1 1 calc R U . . .
C6A C 0.1179(4) 0.16859(10) 0.1639(4) 0.0218(8) Uani 1 1 d . . . . .
H6A H 0.195623 0.169757 0.234853 0.026 Uiso 1 1 calc R U . . .
C1'A C 0.0641(5) 0.10115(10) 0.2347(4) 0.0213(8) Uani 1 1 d . . . . .
H1'A H -0.034417 0.096296 0.289582 0.026 Uiso 1 1 calc R U . . .
C2'A C 0.1101(4) 0.06513(10) 0.1541(4) 0.0211(8) Uani 1 1 d . . . . .
H2'A H 0.057439 0.063492 0.061868 0.025 Uiso 1 1 calc R U . . .
C3'A C 0.2897(5) 0.06993(11) 0.1441(4) 0.0207(8) Uani 1 1 d . . . . .
H3'A H 0.316395 0.088286 0.068802 0.025 Uiso 1 1 calc R U . . .
C4'A C 0.3314(4) 0.08710(10) 0.2836(4) 0.0198(7) Uani 1 1 d . . . . .
H4'A H 0.346243 0.065957 0.351344 0.024 Uiso 1 1 calc R U . . .
C5'A C 0.4773(4) 0.11210(11) 0.2866(4) 0.0225(8) Uani 1 1 d . . . . .
H5'2 H 0.483641 0.125533 0.376237 0.027 Uiso 1 1 calc R U . . .
H5'1 H 0.573808 0.096288 0.276211 0.027 Uiso 1 1 calc R U . . .
P1B P 0.56023(11) 0.18247(3) 0.69363(9) 0.0182(2) Uani 1 1 d . . . . .
O11B O 0.5360(3) 0.20260(7) 0.5597(3) 0.0223(6) Uani 1 1 d . . . . .
O12B O 0.7273(3) 0.17862(8) 0.7448(3) 0.0227(6) Uani 1 1 d . . . . .
O13B O 0.4531(3) 0.20315(8) 0.8039(3) 0.0235(6) Uani 1 1 d . . . . .
H13B H 0.488442 0.198739 0.883331 0.035 Uiso 1 1 calc R U . . .
O2B O -0.1569(3) 0.10208(8) 0.5462(3) 0.0252(6) Uani 1 1 d . . . . .
O2'B O 0.0925(3) 0.03420(7) 0.7355(3) 0.0240(6) Uani 1 1 d . . . . .
H2OB H 0.114193 0.013798 0.694544 0.036 Uiso 1 1 calc R U . . .
O3'B O 0.3926(3) 0.03574(7) 0.6246(3) 0.0251(6) Uani 1 1 d . . . . .
H3OB H 0.461390 0.038068 0.562430 0.038 Uiso 1 1 calc R U . . .
O4'B O 0.2105(3) 0.10993(8) 0.8225(3) 0.0218(6) Uani 1 1 d . . . . .
O5'B O 0.4829(3) 0.14138(7) 0.6751(3) 0.0222(6) Uani 1 1 d . . . . .
N1B N 0.0499(4) 0.13453(9) 0.6434(3) 0.0207(6) Uani 1 1 d . . . . .
N3B N -0.1032(4) 0.16178(9) 0.4696(3) 0.0199(7) Uani 1 1 d . . . . .
H3B H -0.171406 0.158887 0.401625 0.024 Uiso 1 1 calc R U . . .
N4B N -0.0782(4) 0.22399(9) 0.4024(4) 0.0238(7) Uani 1 1 d . . . . .
H41B H -0.153669 0.220164 0.341135 0.029 Uiso 1 1 calc R U . . .
H42B H -0.033541 0.246521 0.409625 0.029 Uiso 1 1 calc R U . . .
C2B C -0.0766(4) 0.13099(11) 0.5541(4) 0.0208(8) Uani 1 1 d . . . . .
C4B C -0.0325(5) 0.19616(11) 0.4828(4) 0.0205(8) Uani 1 1 d . . . . .
C5B C 0.0887(5) 0.19957(11) 0.5846(4) 0.0223(8) Uani 1 1 d . . . . .
H5B H 0.142409 0.223008 0.598599 0.027 Uiso 1 1 calc R U . . .
C6B C 0.1252(4) 0.16854(11) 0.6610(4) 0.0226(8) Uani 1 1 d . . . . .
H6B H 0.205989 0.170512 0.729007 0.027 Uiso 1 1 calc R U . . .
C1'B C 0.0839(4) 0.10074(10) 0.7343(4) 0.0203(8) Uani 1 1 d . . . . .
H1'B H -0.012412 0.094430 0.790137 0.024 Uiso 1 1 calc R U . . .
C2'B C 0.1354(4) 0.06567(10) 0.6502(4) 0.0208(8) Uani 1 1 d . . . . .
H2'B H 0.085475 0.064641 0.556644 0.025 Uiso 1 1 calc R U . . .
C3'B C 0.3152(4) 0.07080(11) 0.6447(4) 0.0205(8) Uani 1 1 d . . . . .
H3'B H 0.344092 0.088880 0.569179 0.025 Uiso 1 1 calc R U . . .
C4'B C 0.3519(4) 0.08847(10) 0.7843(4) 0.0191(7) Uani 1 1 d . . . . .
H4'B H 0.367804 0.067603 0.853018 0.023 Uiso 1 1 calc R U . . .
C5'B C 0.4960(4) 0.11432(11) 0.7873(4) 0.0223(8) Uani 1 1 d . . . . .
H5'3 H 0.501133 0.127943 0.876601 0.027 Uiso 1 1 calc R U . . .
H5'4 H 0.594140 0.099087 0.776870 0.027 Uiso 1 1 calc R U . . .
O1W O 0.6471(4) 0.04287(11) 0.4694(4) 0.0504(10) Uani 1 1 d DG . . . .
H1W H 0.704436 0.063236 0.461561 0.076 Uiso 1 1 d DG U . . .
H2W H 0.692116 0.032277 0.545005 0.076 Uiso 1 1 d DG U . . .
O2W O 0.7188(4) -0.01120(10) 0.2747(3) 0.0362(7) Uani 1 1 d DG . . . .
H3W H 0.716754 0.011897 0.296830 0.054 Uiso 1 1 d DG U . . .
H4W H 0.625053 -0.018405 0.261056 0.054 Uiso 1 1 d DG U . . .
O3W O 0.6501(5) 0.04104(11) 0.0091(5) 0.0606(13) Uani 1 1 d DG . . . .
H5W H 0.695574 0.062238 0.015409 0.091 Uiso 1 1 d DG U . . .
H6W H 0.650573 0.034536 -0.074283 0.091 Uiso 1 1 d DG 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
P1A O11A 1.493(3) . yes
P1A O12A 1.495(3) . yes
P1A O13A 1.577(3) . yes
P1A O5'A 1.598(3) . yes
O13A H13A 0.8400 . ?
O2A C2A 1.229(5) . ?
O2'A C2'A 1.421(5) . ?
O2'A H2OA 0.8400 . ?
O3'A C3'A 1.409(4) . ?
O3'A H3OA 0.8400 . ?
O4'A C1'A 1.409(5) . ?
O4'A C4'A 1.464(4) . ?
O5'A C5'A 1.446(4) . ?
N1A C6A 1.368(5) . ?
N1A C2A 1.379(5) . ?
N1A C1'A 1.505(5) . ?
N3A C4A 1.359(5) . ?
N3A C2A 1.366(5) . ?
N3A H3A 0.8800 . ?
N4A C4A 1.303(5) . ?
N4A H41A 0.8800 . ?
N4A H42A 0.8800 . ?
C4A C5A 1.424(5) . ?
C5A C6A 1.355(5) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C1'A C2'A 1.538(5) . ?
C1'A H1'A 1.0000 . ?
C2'A C3'A 1.525(5) . ?
C2'A H2'A 1.0000 . ?
C3'A C4'A 1.521(5) . ?
C3'A H3'A 1.0000 . ?
C4'A C5'A 1.511(5) . ?
C4'A H4'A 1.0000 . ?
C5'A H5'2 0.9900 . ?
C5'A H5'1 0.9900 . ?
P1B O11B 1.492(3) . yes
P1B O12B 1.498(3) . yes
P1B O13B 1.576(3) . yes
P1B O5'B 1.595(3) . yes
O13B H13B 0.8400 . ?
O2B C2B 1.223(5) . ?
O2'B C2'B 1.428(4) . ?
O2'B H2OB 0.8400 . ?
O3'B C3'B 1.408(4) . ?
O3'B H3OB 0.8400 . ?
O4'B C1'B 1.404(4) . ?
O4'B C4'B 1.458(4) . ?
O5'B C5'B 1.450(4) . ?
N1B C6B 1.364(5) . ?
N1B C2B 1.378(5) . ?
N1B C1'B 1.506(5) . ?
N3B C4B 1.354(5) . ?
N3B C2B 1.376(5) . ?
N3B H3B 0.8800 . ?
N4B C4B 1.309(5) . ?
N4B H41B 0.8800 . ?
N4B H42B 0.8800 . ?
C4B C5B 1.425(5) . ?
C5B C6B 1.354(5) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C1'B C2'B 1.541(5) . ?
C1'B H1'B 1.0000 . ?
C2'B C3'B 1.525(5) . ?
C2'B H2'B 1.0000 . ?
C3'B C4'B 1.520(5) . ?
C3'B H3'B 1.0000 . ?
C4'B C5'B 1.516(5) . ?
C4'B H4'B 1.0000 . ?
C5'B H5'3 0.9900 . ?
C5'B H5'4 0.9900 . ?
O1W H1W 0.8672 . ?
O1W H2W 0.9054 . ?
O2W H3W 0.8403 . ?
O2W H4W 0.8395 . ?
O3W H5W 0.8403 . ?
O3W H6W 0.8396 . ?

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
O11A P1A O12A 117.13(16) . . ?
O11A P1A O13A 107.08(15) . . ?
O12A P1A O13A 110.71(15) . . ?
O11A P1A O5'A 105.88(15) . . yes
O12A P1A O5'A 110.26(15) . . yes
O13A P1A O5'A 105.00(15) . . yes
P1A O13A H13A 109.5 . . ?
C2'A O2'A H2OA 109.5 . . ?
C3'A O3'A H3OA 109.5 . . ?
C1'A O4'A C4'A 110.0(3) . . ?
C5'A O5'A P1A 118.3(2) . . ?
C6A N1A C2A 120.2(3) . . ?
C6A N1A C1'A 121.7(3) . . ?
C2A N1A C1'A 117.3(3) . . ?
C4A N3A C2A 125.7(3) . . ?
C4A N3A H3A 117.2 . . ?
C2A N3A H3A 117.2 . . ?
C4A N4A H41A 120.0 . . ?
C4A N4A H42A 120.0 . . ?
H41A N4A H42A 120.0 . . ?
O2A C2A N3A 121.3(4) . . ?
O2A C2A N1A 122.8(4) . . ?
N3A C2A N1A 115.9(3) . . ?
N4A C4A N3A 118.8(4) . . ?
N4A C4A C5A 124.8(4) . . ?
N3A C4A C5A 116.4(3) . . ?
C6A C5A C4A 118.4(3) . . ?
C6A C5A H5A 120.8 . . ?
C4A C5A H5A 120.8 . . ?
C5A C6A N1A 122.6(4) . . ?
C5A C6A H6A 118.7 . . ?
N1A C6A H6A 118.7 . . ?
O4'A C1'A N1A 108.2(3) . . ?
O4'A C1'A C2'A 106.6(3) . . ?
N1A C1'A C2'A 112.6(3) . . ?
O4'A C1'A H1'A 109.8 . . ?
N1A C1'A H1'A 109.8 . . ?
C2'A C1'A H1'A 109.8 . . ?
O2'A C2'A C3'A 112.3(3) . . ?
O2'A C2'A C1'A 103.8(3) . . ?
C3'A C2'A C1'A 101.0(3) . . ?
O2'A C2'A H2'A 112.9 . . ?
C3'A C2'A H2'A 112.9 . . ?
C1'A C2'A H2'A 112.9 . . ?
O3'A C3'A C4'A 113.5(3) . . ?
O3'A C3'A C2'A 110.9(3) . . ?
C4'A C3'A C2'A 102.5(3) . . ?
O3'A C3'A H3'A 109.9 . . ?
C4'A C3'A H3'A 109.9 . . ?
C2'A C3'A H3'A 109.9 . . ?
O4'A C4'A C5'A 109.9(3) . . ?
O4'A C4'A C3'A 105.3(3) . . ?
C5'A C4'A C3'A 115.8(3) . . ?
O4'A C4'A H4'A 108.5 . . ?
C5'A C4'A H4'A 108.5 . . ?
C3'A C4'A H4'A 108.5 . . ?
O5'A C5'A C4'A 109.3(3) . . ?
O5'A C5'A H5'2 109.8 . . ?
C4'A C5'A H5'2 109.8 . . ?
O5'A C5'A H5'1 109.8 . . ?
C4'A C5'A H5'1 109.8 . . ?
H5'2 C5'A H5'1 108.3 . . ?
O11B P1B O12B 117.36(16) . . ?
O11B P1B O13B 107.01(15) . . ?
O12B P1B O13B 110.77(15) . . ?
O11B P1B O5'B 106.00(15) . . yes
O12B P1B O5'B 109.81(15) . . yes
O13B P1B O5'B 105.11(15) . . yes
P1B O13B H13B 109.5 . . ?
C2'B O2'B H2OB 109.5 . . ?
C3'B O3'B H3OB 109.5 . . ?
C1'B O4'B C4'B 110.3(3) . . ?
C5'B O5'B P1B 118.6(2) . . ?
C6B N1B C2B 121.1(3) . . ?
C6B N1B C1'B 122.0(3) . . ?
C2B N1B C1'B 116.3(3) . . ?
C4B N3B C2B 125.1(3) . . ?
C4B N3B H3B 117.5 . . ?
C2B N3B H3B 117.5 . . ?
C4B N4B H41B 120.0 . . ?
C4B N4B H42B 120.0 . . ?
H41B N4B H42B 120.0 . . ?
O2B C2B N3B 121.8(4) . . ?
O2B C2B N1B 122.8(4) . . ?
N3B C2B N1B 115.4(3) . . ?
N4B C4B N3B 118.8(4) . . ?
N4B C4B C5B 124.1(4) . . ?
N3B C4B C5B 117.1(3) . . ?
C6B C5B C4B 118.3(4) . . ?
C6B C5B H5B 120.9 . . ?
C4B C5B H5B 120.9 . . ?
C5B C6B N1B 122.2(4) . . ?
C5B C6B H6B 118.9 . . ?
N1B C6B H6B 118.9 . . ?
O4'B C1'B N1B 108.6(3) . . ?
O4'B C1'B C2'B 107.0(3) . . ?
N1B C1'B C2'B 112.0(3) . . ?
O4'B C1'B H1'B 109.7 . . ?
N1B C1'B H1'B 109.7 . . ?
C2'B C1'B H1'B 109.7 . . ?
O2'B C2'B C3'B 111.3(3) . . ?
O2'B C2'B C1'B 104.0(3) . . ?
C3'B C2'B C1'B 101.7(3) . . ?
O2'B C2'B H2'B 113.0 . . ?
C3'B C2'B H2'B 113.0 . . ?
C1'B C2'B H2'B 113.0 . . ?
O3'B C3'B C4'B 112.7(3) . . ?
O3'B C3'B C2'B 111.2(3) . . ?
C4'B C3'B C2'B 102.7(3) . . ?
O3'B C3'B H3'B 110.0 . . ?
C4'B C3'B H3'B 110.0 . . ?
C2'B C3'B H3'B 110.0 . . ?
O4'B C4'B C5'B 109.8(3) . . ?
O4'B C4'B C3'B 105.7(3) . . ?
C5'B C4'B C3'B 115.2(3) . . ?
O4'B C4'B H4'B 108.7 . . ?
C5'B C4'B H4'B 108.7 . . ?
C3'B C4'B H4'B 108.7 . . ?
O5'B C5'B C4'B 108.5(3) . . ?
O5'B C5'B H5'3 110.0 . . ?
C4'B C5'B H5'3 110.0 . . ?
O5'B C5'B H5'4 110.0 . . ?
C4'B C5'B H5'4 110.0 . . ?
H5'3 C5'B H5'4 108.4 . . ?
H1W O1W H2W 100.2 . . ?
H3W O2W H4W 108.2 . . ?
H5W O3W H6W 108.0 . . ?

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
O11A P1A O5'A C5'A 174.3(2) . . . . ?
O12A P1A O5'A C5'A 46.7(3) . . . . ?
O13A P1A O5'A C5'A -72.6(3) . . . . ?
C4A N3A C2A O2A 171.9(4) . . . . ?
C4A N3A C2A N1A -10.6(6) . . . . ?
C6A N1A C2A O2A -172.4(4) . . . . ?
C1'A N1A C2A O2A -2.3(5) . . . . ?
C6A N1A C2A N3A 10.1(5) . . . . ?
C1'A N1A C2A N3A -179.8(3) . . . . ?
C2A N3A C4A N4A -174.8(4) . . . . ?
C2A N3A C4A C5A 5.5(6) . . . . ?
N4A C4A C5A C6A -179.5(4) . . . . ?
N3A C4A C5A C6A 0.1(5) . . . . ?
C4A C5A C6A N1A 0.0(6) . . . . ?
C2A N1A C6A C5A -5.4(6) . . . . ?
C1'A N1A C6A C5A -175.0(4) . . . . ?
C4'A O4'A C1'A N1A -107.1(3) . . . . ?
C4'A O4'A C1'A C2'A 14.2(4) . . . . ?
C6A N1A C1'A O4'A -8.8(5) . . . . ?
C2A N1A C1'A O4'A -178.7(3) . . . . yes
C6A N1A C1'A C2'A -126.3(4) . . . . ?
C2A N1A C1'A C2'A 63.8(4) . . . . ?
O4'A C1'A C2'A O2'A 83.9(3) . . . . ?
N1A C1'A C2'A O2'A -157.6(3) . . . . ?
O4'A C1'A C2'A C3'A -32.5(4) . . . . ?
N1A C1'A C2'A C3'A 86.0(4) . . . . ?
O2'A C2'A C3'A O3'A 48.8(4) . . . . ?
C1'A C2'A C3'A O3'A 158.8(3) . . . . ?
O2'A C2'A C3'A C4'A -72.6(4) . . . . ?
C1'A C2'A C3'A C4'A 37.4(4) . . . . ?
C1'A O4'A C4'A C5'A 135.7(3) . . . . ?
C1'A O4'A C4'A C3'A 10.2(4) . . . . ?
O3'A C3'A C4'A O4'A -150.0(3) . . . . ?
C2'A C3'A C4'A O4'A -30.3(4) . . . . ?
O3'A C3'A C4'A C5'A 88.4(4) . . . . ?
C2'A C3'A C4'A C5'A -151.9(3) . . . . ?
P1A O5'A C5'A C4'A 151.5(2) . . . . ?
O4'A C4'A C5'A O5'A -69.9(4) . . . . ?
C3'A C4'A C5'A O5'A 49.3(4) . . . . ?
O11B P1B O5'B C5'B 176.7(3) . . . . ?
O12B P1B O5'B C5'B 49.0(3) . . . . ?
O13B P1B O5'B C5'B -70.2(3) . . . . ?
C4B N3B C2B O2B 171.8(4) . . . . ?
C4B N3B C2B N1B -10.8(6) . . . . ?
C6B N1B C2B O2B -172.4(4) . . . . ?
C1'B N1B C2B O2B -1.0(5) . . . . ?
C6B N1B C2B N3B 10.2(5) . . . . ?
C1'B N1B C2B N3B -178.4(3) . . . . ?
C2B N3B C4B N4B -174.4(4) . . . . ?
C2B N3B C4B C5B 5.8(6) . . . . ?
N4B C4B C5B C6B -179.8(4) . . . . ?
N3B C4B C5B C6B 0.0(5) . . . . ?
C4B C5B C6B N1B -0.1(6) . . . . ?
C2B N1B C6B C5B -5.3(6) . . . . ?
C1'B N1B C6B C5B -176.2(4) . . . . ?
C4'B O4'B C1'B N1B -110.0(3) . . . . ?
C4'B O4'B C1'B C2'B 11.1(4) . . . . ?
C6B N1B C1'B O4'B -5.8(5) . . . . ?
C2B N1B C1'B O4'B -177.2(3) . . . . yes
C6B N1B C1'B C2'B -123.8(4) . . . . ?
C2B N1B C1'B C2'B 64.9(4) . . . . ?
O4'B C1'B C2'B O2'B 86.7(3) . . . . ?
N1B C1'B C2'B O2'B -154.3(3) . . . . ?
O4'B C1'B C2'B C3'B -29.0(4) . . . . ?
N1B C1'B C2'B C3'B 89.9(3) . . . . ?
O2'B C2'B C3'B O3'B 45.2(4) . . . . ?
C1'B C2'B C3'B O3'B 155.5(3) . . . . ?
O2'B C2'B C3'B C4'B -75.6(4) . . . . ?
C1'B C2'B C3'B C4'B 34.7(4) . . . . ?
C1'B O4'B C4'B C5'B 136.5(3) . . . . ?
C1'B O4'B C4'B C3'B 11.7(4) . . . . ?
O3'B C3'B C4'B O4'B -149.1(3) . . . . ?
C2'B C3'B C4'B O4'B -29.4(4) . . . . ?
O3'B C3'B C4'B C5'B 89.5(4) . . . . ?
C2'B C3'B C4'B C5'B -150.8(3) . . . . ?
P1B O5'B C5'B C4'B 149.8(2) . . . . ?
O4'B C4'B C5'B O5'B -69.0(4) . . . . ?
C3'B C4'B C5'B O5'B 50.1(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

O13A H13A O11B 0.84 1.78 2.598(4) 163.8 .
O2'A H2OA O3'B 0.84 1.93 2.763(4) 174.6 2_554
O3'A H3OA O3W 0.84 1.81 2.640(5) 169.8 .
O13B H13B O11A 0.84 1.77 2.592(4) 166.5 1_556
O2'B H2OB O3'A 0.84 1.87 2.699(4) 170.9 2
O3'B H3OB O1W 0.84 1.81 2.631(5) 163.9 .
O1W H1W O2B 0.87 1.98 2.759(4) 149.8 1_655
O1W H2W O2W 0.91 2.46 3.357(6) 169.4 2_655
O2W H4W O2'B 0.84 1.93 2.770(4) 178.1 2_554
O2W H3W O1W 0.84 2.08 2.746(5) 135.8 .
O3W H5W O2A 0.84 1.90 2.733(5) 169.5 1_655
O3W H6W O2W 0.84 2.01 2.735(5) 144.7 2_654
N3A H3A O12B 0.88 1.80 2.628(4) 155.0 1_454
N4A H42A O11A 0.88 1.91 2.778(4) 168.4 4_455
N4A H41A O12B 0.88 2.13 2.853(4) 139.6 1_454
N3B H3B O12A 0.88 1.81 2.633(4) 154.9 1_455
N4B H42B O11B 0.88 1.91 2.779(4) 171.5 4_456
N4B H41B O12A 0.88 2.14 2.864(4) 139.0 1_455
C6A H6A O13A 0.95 2.51 3.313(5) 142.8 .
C6A H6A O5'A 0.95 2.60 3.128(5) 115.6 .
C2'A H2'A O2A 1.00 2.40 2.958(5) 114.3 .
C3'A H3'A O4'B 1.00 2.66 3.485(5) 139.9 1_554
C6B H6B O13B 0.95 2.49 3.321(5) 146.7 .
C6B H6B O5'B 0.95 2.60 3.163(5) 118.3 .
C2'B H2'B O2B 1.00 2.43 2.952(5) 111.8 .

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.079


_vrf_PLAT417_VII_LT              
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PROBLEM: Short Inter D-H..H-D       H2W      ..H3OB     .       1.96 Ang.  
RESPONSE: The short D-H..H-D distances are water...hydroxyl distances.
Adopted model for water H atoms is rational, leads to correct hydrogen bonds,
but is probably not perfect.
;
_vrf_PLAT934_VII_LT              
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check 
RESPONSE: This crystal was measured at low temperature after phase transition.
;
