# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1231-kp-04-56
_database_code_depnum_ccdc_archive 'CCDC 2307658'
loop_
_audit_author_name
_audit_author_address
'Michelle Neary'
;Hunter College
United States of America
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N3 O6, H2 O'
_chemical_formula_sum            'C9 H15 N3 O7'
_chemical_formula_weight         277.24

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'

_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                   5.13410(10)
_cell_length_b                   8.4181(2)
_cell_length_c                   13.3376(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.2350(10)
_cell_angle_gamma                90
_cell_volume                     575.52(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      6.22
_cell_measurement_theta_max      74.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.204
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 with PHOTON III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10465
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.319
_diffrn_reflns_theta_max         74.378
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2288
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.961

_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0485P)²+0.1386P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.14(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2288
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_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
O1 O 1.1072(3) 0.47104(17) 0.45716(11) 0.0185(3) Uani 1 1 d . . . . .
H1 H 1.229(6) 0.528(4) 0.426(2) 0.022 Uiso 1 1 d . U . . .
O2 O 0.5833(3) 0.15324(16) 0.64200(12) 0.0179(3) Uani 1 1 d . . . . .
O3 O 0.0708(3) 0.42508(16) 0.78142(10) 0.0132(3) Uani 1 1 d . . . . .
O4 O 0.2656(3) 0.12309(17) 0.88215(10) 0.0155(3) Uani 1 1 d . . . . .
H4 H 0.364(6) 0.066(4) 0.913(2) 0.019 Uiso 1 1 d . U . . .
O5 O 0.4596(3) 0.38143(17) 1.01565(9) 0.0146(3) Uani 1 1 d . . . . .
H5 H 0.350(6) 0.314(4) 1.042(2) 0.017 Uiso 1 1 d . U . . .
O6 O -0.1643(3) 0.69367(18) 0.87426(12) 0.0164(3) Uani 1 1 d . . . . .
H6 H -0.139(6) 0.749(4) 0.826(2) 0.020 Uiso 1 1 d . U . . .
N1 N 0.9623(3) 0.5939(2) 0.50232(13) 0.0166(4) Uani 1 1 d . . . . .
N2 N 0.7617(3) 0.3688(2) 0.56871(12) 0.0148(3) Uani 1 1 d . . . . .
H2 H 0.872(6) 0.309(4) 0.534(2) 0.018 Uiso 1 1 d . U . . .
N3 N 0.4355(3) 0.3965(2) 0.68216(12) 0.0136(3) Uani 1 1 d . . . . .
C1 C 0.7898(4) 0.5318(2) 0.55776(15) 0.0143(4) Uani 1 1 d . . . . .
C2 C 0.6146(4) 0.6294(2) 0.61154(14) 0.0154(4) Uani 1 1 d . . . . .
H2A H 0.619105 0.741745 0.605056 0.018 Uiso 1 1 calc R U . . .
C3 C 0.4454(4) 0.5607(2) 0.67073(15) 0.0147(4) Uani 1 1 d . . . . .
H3A H 0.329237 0.625485 0.705759 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5936(4) 0.2986(2) 0.63089(14) 0.0140(4) Uani 1 1 d . . . . .
C5 C 0.2584(4) 0.3156(2) 0.75019(14) 0.0127(4) Uani 1 1 d . . . . .
H5A H 0.168595 0.225124 0.714003 0.015 Uiso 1 1 calc R U . . .
C6 C 0.4083(4) 0.2536(2) 0.84533(14) 0.0128(4) Uani 1 1 d . . . . .
H6A H 0.592417 0.224402 0.832740 0.015 Uiso 1 1 calc R U . . .
C7 C 0.3923(3) 0.4008(2) 0.91224(14) 0.0123(4) Uani 1 1 d . . . . .
H7A H 0.512161 0.482677 0.886026 0.015 Uiso 1 1 calc R U . . .
C8 C 0.1133(3) 0.4571(2) 0.88776(13) 0.0119(4) Uani 1 1 d . . . . .
H8A H -0.011286 0.393714 0.926656 0.014 Uiso 1 1 calc R U . . .
C9 C 0.0834(4) 0.6320(2) 0.90981(14) 0.0149(4) Uani 1 1 d . . . . .
H9A H 0.105571 0.648935 0.983243 0.018 Uiso 1 1 calc R U . . .
H9B H 0.223075 0.691504 0.877970 0.018 Uiso 1 1 calc R U . . .
O7 O 0.0828(4) 0.8740(2) 0.73837(13) 0.0282(4) Uani 1 1 d . . . . .
H7B H 0.138(7) 0.960(5) 0.771(3) 0.034 Uiso 1 1 d . U . . .
H7C H 0.035(6) 0.907(4) 0.680(3) 0.034 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.427(2) . ?
O1 H1 0.90(3) . ?
O2 C4 1.234(3) . ?
O3 C5 1.413(2) . ?
O3 C8 1.448(2) . ?
O4 C6 1.423(2) . ?
O4 H4 0.79(3) . ?
O5 C7 1.412(2) . ?
O5 H5 0.89(3) . ?
O6 C9 1.430(2) . ?
O6 H6 0.81(3) . ?
N1 C1 1.295(3) . ?
N2 C4 1.365(3) . ?
N2 C1 1.389(3) . ?
N2 H2 0.90(3) . ?
N3 C4 1.366(3) . ?
N3 C3 1.392(2) . ?
N3 C5 1.486(2) . ?
C1 C2 1.439(3) . ?
C2 C3 1.338(3) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C5 C6 1.538(2) . ?
C5 H5A 1.0000 . ?
C6 C7 1.532(2) . ?
C6 H6A 1.0000 . ?
C7 C8 1.527(2) . ?
C7 H7A 1.0000 . ?
C8 C9 1.511(3) . ?
C8 H8A 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O7 H7B 0.88(4) . ?
O7 H7C 0.85(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 H1 101(2) . . ?
C5 O3 C8 110.03(14) . . ?
C6 O4 H4 109(2) . . ?
C7 O5 H5 109.7(18) . . ?
C9 O6 H6 107(2) . . ?
C1 N1 O1 109.74(16) . . ?
C4 N2 C1 124.37(17) . . ?
C4 N2 H2 120.6(19) . . ?
C1 N2 H2 114.9(19) . . ?
C4 N3 C3 121.16(17) . . ?
C4 N3 C5 115.51(16) . . ?
C3 N3 C5 123.32(16) . . ?
N1 C1 N2 122.50(18) . . ?
N1 C1 C2 121.38(18) . . ?
N2 C1 C2 116.12(18) . . ?
C3 C2 C1 119.50(19) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 N3 121.51(19) . . ?
C2 C3 H3A 119.2 . . ?
N3 C3 H3A 119.2 . . ?
O2 C4 N2 122.33(19) . . ?
O2 C4 N3 120.46(18) . . ?
N2 C4 N3 117.22(18) . . ?
O3 C5 N3 109.38(15) . . ?
O3 C5 C6 107.21(15) . . ?
N3 C5 C6 111.38(14) . . ?
O3 C5 H5A 109.6 . . ?
N3 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
O4 C6 C7 112.20(15) . . ?
O4 C6 C5 107.66(14) . . ?
C7 C6 C5 99.52(14) . . ?
O4 C6 H6A 112.2 . . ?
C7 C6 H6A 112.2 . . ?
C5 C6 H6A 112.2 . . ?
O5 C7 C8 114.80(15) . . ?
O5 C7 C6 117.21(15) . . ?
C8 C7 C6 101.93(14) . . ?
O5 C7 H7A 107.4 . . ?
C8 C7 H7A 107.4 . . ?
C6 C7 H7A 107.4 . . ?
O3 C8 C9 111.13(15) . . ?
O3 C8 C7 103.86(14) . . ?
C9 C8 C7 111.41(15) . . ?
O3 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
O6 C9 C8 112.81(15) . . ?
O6 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
O6 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
H7B O7 H7C 105(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
O1 N1 C1 N2 0.3(3) . . . . ?
O1 N1 C1 C2 -179.42(16) . . . . ?
C4 N2 C1 N1 175.92(18) . . . . ?
C4 N2 C1 C2 -4.3(3) . . . . ?
N1 C1 C2 C3 -177.70(18) . . . . ?
N2 C1 C2 C3 2.5(3) . . . . ?
C1 C2 C3 N3 0.4(3) . . . . ?
C4 N3 C3 C2 -2.0(3) . . . . ?
C5 N3 C3 C2 177.44(17) . . . . ?
C1 N2 C4 O2 -176.51(18) . . . . ?
C1 N2 C4 N3 2.9(3) . . . . ?
C3 N3 C4 O2 179.77(17) . . . . ?
C5 N3 C4 O2 0.3(3) . . . . ?
C3 N3 C4 N2 0.3(3) . . . . ?
C5 N3 C4 N2 -179.09(15) . . . . ?
C8 O3 C5 N3 -112.27(16) . . . . ?
C8 O3 C5 C6 8.63(19) . . . . ?
C4 N3 C5 O3 -167.72(15) . . . . ?
C3 N3 C5 O3 12.9(2) . . . . ?
C4 N3 C5 C6 74.0(2) . . . . ?
C3 N3 C5 C6 -105.5(2) . . . . ?
O3 C5 C6 O4 86.18(17) . . . . ?
N3 C5 C6 O4 -154.19(14) . . . . ?
O3 C5 C6 C7 -30.92(17) . . . . ?
N3 C5 C6 C7 88.71(17) . . . . ?
O4 C6 C7 O5 52.9(2) . . . . ?
C5 C6 C7 O5 166.51(15) . . . . ?
O4 C6 C7 C8 -73.31(17) . . . . ?
C5 C6 C7 C8 40.31(16) . . . . ?
C5 O3 C8 C9 137.70(15) . . . . ?
C5 O3 C8 C7 17.81(19) . . . . ?
O5 C7 C8 O3 -164.60(14) . . . . ?
C6 C7 C8 O3 -36.83(17) . . . . ?
O5 C7 C8 C9 75.7(2) . . . . ?
C6 C7 C8 C9 -156.53(15) . . . . ?
O3 C8 C9 O6 56.1(2) . . . . ?
C7 C8 C9 O6 171.44(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
_geom_hbond_publ_flag
O1 H1 O2 0.90(3) 1.72(3) 2.620(2) 171(3) 2_756 yes
N2 H2 N1 0.90(3) 2.07(3) 2.900(2) 152(3) 2_746 yes
O4 H4 O5 0.79(3) 2.01(3) 2.787(2) 165(3) 2_647 yes
O5 H5 O6 0.89(3) 1.82(3) 2.684(2) 165(3) 2_547 yes
O6 H6 O7 0.81(3) 1.98(3) 2.731(2) 153(3) . yes
O7 H7B O4 0.88(4) 2.10(4) 2.958(2) 164(3) 1_565 yes
O7 H7C O1 0.85(4) 2.00(4) 2.852(2) 175(3) 2_656 yes

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037

