# Supplementary Information (SI) 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_pno2ppinb
_database_code_depnum_ccdc_archive 'CCDC 2341020'
loop_
_audit_author_name
_audit_author_address
'Jan Kotek'
;Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-03-18 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N O6 P2'
_chemical_formula_sum            'C8 H11 N O6 P2'
_chemical_formula_weight         279.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.3534(4)
_cell_length_b                   8.1042(2)
_cell_length_c                   10.3592(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.7720(10)
_cell_angle_gamma                90
_cell_volume                     1120.52(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.9406
_cell_measurement_theta_max      27.4914

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.622
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    0.405
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            20659
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2559
_reflns_number_gt                2458
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0355P)²+0.6389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2559
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.55272(2) 0.73621(4) 0.57944(3) 0.01646(9) Uani 1 1 d . . . . .
H1 H 0.545231 0.749122 0.444126 0.020 Uiso 1 1 d R U . . .
O11 O 0.61833(7) 0.58065(12) 0.59907(9) 0.0232(2) Uani 1 1 d . . . . .
H11O H 0.6265(18) 0.553(3) 0.680(2) 0.063(7) Uiso 1 1 d . . . . .
O12 O 0.59259(7) 0.89304(12) 0.63677(9) 0.0232(2) Uani 1 1 d . . . . .
C1 C 0.43180(9) 0.68931(15) 0.64155(12) 0.0180(2) Uani 1 1 d . . . . .
H11 H 0.438901 0.678459 0.736578 0.022 Uiso 1 1 calc R U . . .
H12 H 0.410009 0.580820 0.606892 0.022 Uiso 1 1 calc R U . . .
P2 P 0.33484(2) 0.83749(4) 0.60497(3) 0.01583(9) Uani 1 1 d . . . . .
O21 O 0.33077(7) 0.85571(11) 0.45554(8) 0.02055(19) Uani 1 1 d . . . . .
H21O H 0.3558(16) 0.943(3) 0.432(2) 0.046(6) Uiso 1 1 d . . . . .
O22 O 0.35221(7) 0.99876(11) 0.67291(9) 0.02186(19) Uani 1 1 d . . . . .
C2 C 0.21928(9) 0.74547(15) 0.65254(12) 0.0189(2) Uani 1 1 d . . . . .
H21 H 0.224659 0.722066 0.746296 0.023 Uiso 1 1 calc R U . . .
H22 H 0.165129 0.827682 0.639048 0.023 Uiso 1 1 calc R U . . .
C3 C 0.18824(9) 0.58848(15) 0.58379(11) 0.0167(2) Uani 1 1 d . . . . .
C4 C 0.13259(9) 0.59579(15) 0.46717(11) 0.0179(2) Uani 1 1 d . . . . .
H41 H 0.117694 0.699868 0.428990 0.021 Uiso 1 1 calc R U . . .
C5 C 0.09900(9) 0.45246(15) 0.40689(12) 0.0186(2) Uani 1 1 d . . . . .
H51 H 0.060791 0.456965 0.328079 0.022 Uiso 1 1 calc R U . . .
C6 C 0.12255(9) 0.30253(15) 0.46447(12) 0.0181(2) Uani 1 1 d . . . . .
N6 N 0.08219(8) 0.15123(13) 0.40521(11) 0.0225(2) Uani 1 1 d . . . . .
O61 O 0.01925(8) 0.16460(12) 0.31706(10) 0.0286(2) Uani 1 1 d . . . . .
O62 O 0.11284(9) 0.01758(12) 0.44629(12) 0.0369(3) Uani 1 1 d . . . . .
C7 C 0.18006(9) 0.29016(16) 0.57775(13) 0.0206(2) Uani 1 1 d . . . . .
H71 H 0.196757 0.185585 0.613836 0.025 Uiso 1 1 calc R U . . .
C8 C 0.21254(9) 0.43505(16) 0.63691(12) 0.0198(2) Uani 1 1 d . . . . .
H81 H 0.251909 0.429587 0.714764 0.024 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 1.4941(9) . ?
P1 O11 1.5450(10) . ?
P1 C1 1.7973(12) . ?
P1 H1 1.4062 . ?
O11 H11O 0.87(2) . ?
C1 P2 1.7976(12) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
P2 O22 1.4991(9) . ?
P2 O21 1.5543(9) . ?
P2 C2 1.7964(13) . ?
O21 H21O 0.82(2) . ?
C2 C3 1.5099(16) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 C8 1.3940(17) . ?
C3 C4 1.3999(16) . ?
C4 C5 1.3867(17) . ?
C4 H41 0.9500 . ?
C5 C6 1.3854(17) . ?
C5 H51 0.9500 . ?
C6 C7 1.3862(17) . ?
C6 N6 1.4664(15) . ?
N6 O61 1.2266(15) . ?
N6 O62 1.2292(15) . ?
C7 C8 1.3878(18) . ?
C7 H71 0.9500 . ?
C8 H81 0.9500 . ?

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 116.63(6) . . ?
O12 P1 C1 110.53(6) . . ?
O11 P1 C1 107.00(6) . . ?
O12 P1 H1 110.3 . . ?
O11 P1 H1 102.4 . . ?
C1 P1 H1 109.6 . . ?
P1 O11 H11O 112.8(16) . . ?
P1 C1 P2 115.62(7) . . ?
P1 C1 H11 108.4 . . ?
P2 C1 H11 108.4 . . ?
P1 C1 H12 108.4 . . ?
P2 C1 H12 108.4 . . ?
H11 C1 H12 107.4 . . ?
O22 P2 O21 112.64(5) . . ?
O22 P2 C2 110.78(6) . . ?
O21 P2 C2 107.98(6) . . ?
O22 P2 C1 112.55(6) . . ?
O21 P2 C1 106.04(6) . . ?
C2 P2 C1 106.50(6) . . ?
P2 O21 H21O 112.3(14) . . ?
C3 C2 P2 116.49(9) . . ?
C3 C2 H21 108.2 . . ?
P2 C2 H21 108.2 . . ?
C3 C2 H22 108.2 . . ?
P2 C2 H22 108.2 . . ?
H21 C2 H22 107.3 . . ?
C8 C3 C4 119.30(11) . . ?
C8 C3 C2 120.55(10) . . ?
C4 C3 C2 120.14(11) . . ?
C5 C4 C3 120.58(11) . . ?
C5 C4 H41 119.7 . . ?
C3 C4 H41 119.7 . . ?
C6 C5 C4 118.35(11) . . ?
C6 C5 H51 120.8 . . ?
C4 C5 H51 120.8 . . ?
C5 C6 C7 122.71(11) . . ?
C5 C6 N6 118.53(11) . . ?
C7 C6 N6 118.74(11) . . ?
O61 N6 O62 123.28(11) . . ?
O61 N6 C6 118.18(11) . . ?
O62 N6 C6 118.54(11) . . ?
C6 C7 C8 118.04(11) . . ?
C6 C7 H71 121.0 . . ?
C8 C7 H71 121.0 . . ?
C7 C8 C3 120.97(11) . . ?
C7 C8 H81 119.5 . . ?
C3 C8 H81 119.5 . . ?

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.050

