# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_(3AP)(H2PO4)
_database_code_depnum_ccdc_archive 'CCDC 2343554'
loop_
_audit_author_name
_audit_author_address
'Jin Chen'
;Fujian Normal University
China
;
_audit_update_record             
;
2024-05-11 deposited with the CCDC.	2024-06-08 downloaded from the CCDC.
;
_audit_creation_date             2024-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H2 O4 P, C6 H7 N2 O'
_chemical_formula_sum            'C6 H9 N2 O5 P'
_chemical_formula_weight         220.12
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O P F'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   35.3496(12)
_cell_length_b                   14.3166(5)
_cell_length_c                   7.1073(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3596.9(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3224
_cell_measurement_temperature    299.73(10)
_cell_measurement_theta_max      77.5640
_cell_measurement_theta_min      4.9600
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    2.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3916
_diffrn_reflns_point_group_measured_fraction_full 0.764
_diffrn_reflns_point_group_measured_fraction_max 0.730
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.848
_diffrn_reflns_theta_min         5.004
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.73(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     62.00  88.00   0.50    0.07    --  108.75-111.00-167.00   52
  2  ω     36.00  84.00   0.50    0.05    --   45.83-111.00-167.00   96
  3  ω     -9.00  19.00   0.50    0.05    --  -45.83  19.00 -60.00   56
  4  ω     80.00 105.00   0.50    0.07    --  108.75 -95.00-180.00   50
  5  ω     73.00  98.00   0.50    0.07    --  108.75 -95.00-150.00   50
  6  ω     48.00  73.00   0.50    0.07    --  108.75 -95.00-180.00   50
  7  ω   -131.00-104.00   0.50    0.07    -- -104.50 -17.00   2.00   54
  8  ω   -117.00 -31.00   0.50    0.05    --  -45.83 -57.00-180.00  172
  9  ω     64.00 108.00   0.50    0.07    --  108.75 -81.00 141.48   88
 10  ω     41.00  75.00   0.50    0.07    --  108.75 -61.00 -30.00   68
 11  ω     49.00  74.00   0.50    0.07    --  108.75 -61.00   0.00   50
 12  ω     39.00  93.00   0.50    0.07    --  108.75 -77.00 -90.00  108
 13  ω     40.00  67.00   0.50    0.07    --  108.75 -61.00-180.00   54
 14  ω     93.00 118.00   0.50    0.07    --  108.75  15.00-150.00   50
 15  ω    120.00 173.00   0.50    0.07    --  108.75  61.00-180.00  106
 16  ω    130.00 177.00   0.50    0.07    --  108.75 125.00   0.00   94
 17  ω    102.00 142.00   0.50    0.07    --  108.75 122.00  11.00   80
 18  ω     93.00 141.50   0.50    0.07    --  108.75  61.00 120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0383002000
_diffrn_orient_matrix_UB_12      0.0513917000
_diffrn_orient_matrix_UB_13      -0.0011010000
_diffrn_orient_matrix_UB_21      -0.0203468000
_diffrn_orient_matrix_UB_22      0.0921119000
_diffrn_orient_matrix_UB_23      -0.0480999000
_diffrn_orient_matrix_UB_31      -0.0044420000
_diffrn_orient_matrix_UB_32      0.0212196000
_diffrn_orient_matrix_UB_33      0.2113285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.382
_reflns_Friedel_fraction_full    0.500
_reflns_Friedel_fraction_max     0.440
_reflns_number_gt                1319
_reflns_number_total             1399
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.00015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1399
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0701
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.34877(2) 0.38474(4) 0.26849(7) 0.03486(18) Uani 1 1 d . . . . .
O1 O 0.51293(5) 0.38108(19) 0.2712(3) 0.0595(6) Uani 1 1 d . . . . .
O2 O 0.35888(5) 0.43167(16) 0.4514(3) 0.0442(4) Uani 1 1 d . . . . .
O3 O 0.33495(6) 0.44894(15) 0.1175(3) 0.0475(5) Uani 1 1 d . . . . .
O4 O 0.31784(6) 0.30790(14) 0.3061(3) 0.0502(5) Uani 1 1 d . . . . .
H4A H 0.300916 0.329985 0.371299 0.075 Uiso 1 1 calc R U . . .
O5 O 0.38286(6) 0.32864(17) 0.1872(3) 0.0489(5) Uani 1 1 d . . . . .
H5A H 0.389675 0.289366 0.264046 0.073 Uiso 1 1 calc R U . . .
N1 N 0.42280(6) 0.40071(16) 0.6178(3) 0.0378(5) Uani 1 1 d . . . . .
H1 H 0.401072 0.413400 0.569821 0.045 Uiso 1 1 calc R U . . .
N2 N 0.55474(6) 0.3538(2) 0.5037(4) 0.0480(6) Uani 1 1 d . . . . .
H2A H 0.573480 0.350635 0.426868 0.058 Uiso 1 1 calc R U . . .
H2B H 0.558424 0.346564 0.622446 0.058 Uiso 1 1 calc R U . . .
C1 C 0.52030(8) 0.3699(2) 0.4395(4) 0.0414(6) Uani 1 1 d . . . . .
C2 C 0.48826(7) 0.37570(18) 0.5773(3) 0.0357(5) Uani 1 1 d . . . . .
C3 C 0.45296(7) 0.39564(18) 0.5054(4) 0.0371(5) Uani 1 1 d . . . . .
H3 H 0.450128 0.405698 0.376924 0.045 Uiso 1 1 calc R U . . .
C4 C 0.42553(8) 0.3866(2) 0.8030(4) 0.0417(6) Uani 1 1 d . . . . .
H4 H 0.404010 0.389565 0.878021 0.050 Uiso 1 1 calc R U . . .
C5 C 0.45999(9) 0.3676(2) 0.8828(4) 0.0475(7) Uani 1 1 d . . . . .
H5 H 0.462022 0.358666 1.012044 0.057 Uiso 1 1 calc R U . . .
C6 C 0.49160(7) 0.36192(19) 0.7698(4) 0.0419(6) Uani 1 1 d . . . . .
H6 H 0.515095 0.348881 0.822502 0.050 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 O2 1.506(2) . ?
P1 O3 1.495(2) . ?
P1 O4 1.574(2) . ?
P1 O5 1.559(2) . ?
O1 C1 1.235(4) . ?
O4 H4A 0.8200 . ?
O5 H5A 0.8200 . ?
N1 H1 0.8600 . ?
N1 C3 1.334(3) . ?
N1 C4 1.335(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.320(4) . ?
C1 C2 1.500(4) . ?
C2 C3 1.378(3) . ?
C2 C6 1.388(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.371(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O4 109.27(12) . . ?
O2 P1 O5 111.47(12) . . ?
O3 P1 O2 115.00(13) . . ?
O3 P1 O4 108.94(12) . . ?
O3 P1 O5 107.66(12) . . ?
O5 P1 O4 103.88(13) . . ?
P1 O4 H4A 109.5 . . ?
P1 O5 H5A 109.5 . . ?
C3 N1 H1 119.2 . . ?
C3 N1 C4 121.6(2) . . ?
C4 N1 H1 119.2 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
O1 C1 N2 123.5(3) . . ?
O1 C1 C2 117.8(2) . . ?
N2 C1 C2 118.7(3) . . ?
C3 C2 C1 116.9(2) . . ?
C3 C2 C6 118.2(2) . . ?
C6 C2 C1 124.9(2) . . ?
N1 C3 C2 120.8(2) . . ?
N1 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
N1 C4 H4 119.9 . . ?
N1 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C2 C6 H6 120.1 . . ?
C5 C6 C2 119.8(2) . . ?
C5 C6 H6 120.1 . . ?

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
O4 H4A O1 0.82 1.80 2.621(3) 175.3 15_455 yes
O5 H5A O3 0.82 1.74 2.527(3) 160.7 16_545 yes
N1 H1 O2 0.86 1.73 2.589(3) 173.6 . yes
N2 H2A O2 0.86 2.09 2.922(3) 164.3 7_554 yes
N2 H2B O3 0.86 2.08 2.898(3) 157.9 7 yes

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 C1 C2 C3 -1.7(4) . . . . ?
O1 C1 C2 C6 177.8(3) . . . . ?
N1 C4 C5 C6 -1.0(5) . . . . ?
N2 C1 C2 C3 177.9(3) . . . . ?
N2 C1 C2 C6 -2.5(5) . . . . ?
C1 C2 C3 N1 179.0(2) . . . . ?
C1 C2 C6 C5 -179.0(3) . . . . ?
C3 N1 C4 C5 1.0(4) . . . . ?
C3 C2 C6 C5 0.5(4) . . . . ?
C4 N1 C3 C2 -0.2(4) . . . . ?
C4 C5 C6 C2 0.2(5) . . . . ?
C6 C2 C3 N1 -0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.514
_oxdiff_exptl_absorpt_empirical_full_min 0.671
####################################################################### 
# 
# 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_(3CP)(H2PO4)
_database_code_depnum_ccdc_archive 'CCDC 2343555'
loop_
_audit_author_name
_audit_author_address
'Jin Chen'
;Fujian Normal University
China
;
_audit_update_record             
;
2024-05-11 deposited with the CCDC.	2024-06-08 downloaded from the CCDC.
;
_audit_creation_date             2024-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H2 O4 P, C6 H6 N O2'
_chemical_formula_sum            'C6 H8 N O6 P'
_chemical_formula_weight         221.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H9N2O5P
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   12.9290(2)
_cell_length_b                   7.69510(10)
_cell_length_c                   17.0913(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1700.41(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6070
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.3880
_cell_measurement_theta_min      6.1930
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.660
_exptl_absorpt_coefficient_mu    3.021
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 -1 2 0.0743
0 -3 9 0.0318
2 3 -9 0.0227
2 -2 10 0.0291
-7 -2 -3 0.0532
0 0 11 0.0296
1 4 7 0.0647
-2 -5 1 0.0447
-3 1 10 0.0428
-3 -1 10 0.0285
-5 -1 8 0.0339
-7 -2 5 0.0404
-7 -3 1 0.0448
2 0 11 0.0365
-4 -2 -9 0.0520
-4 -4 -4 0.0456
0 -4 -7 0.0516
-2 0 11 0.0296
2 -4 -6 0.0533
4 -4 -4 0.0577
-4 4 4 0.0725
6 -3 -2 0.0629
2 -4 7 0.0348
-8 2 0 0.0734

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.0920 -1.0054 1.9152 0.5675 -0.8233 -0.0094
0.1380 -3.0159 8.8396 0.1640 -0.2316 0.9589
2.1794 2.8371 -8.6611 -0.0098 0.0029 -0.9999
1.8480 -1.5529 10.2547 0.5185 -0.1796 0.8360
-7.1651 -2.1746 -3.1708 -0.9115 0.3223 0.2557
-0.1860 -0.3727 11.0568 0.5449 0.1651 0.8221
0.5040 3.9962 6.6269 0.8233 0.5675 -0.0095
-1.8496 -4.8679 0.5348 -0.6246 -0.4280 0.6532
-3.0213 1.2744 9.9525 0.4617 0.6068 0.6470
-2.9594 -0.6085 10.2886 0.2820 0.3732 0.8838
-5.4383 -0.5249 8.3638 0.0117 0.5740 0.8188
-6.8576 -1.5616 5.3677 -0.3620 0.5209 0.7731
-6.7367 -2.9492 0.9342 -0.7423 0.2595 0.6177
2.2736 -0.0221 10.6766 0.7359 -0.0205 0.6768
-4.2522 -1.6460 -8.8382 -0.9554 0.0247 -0.2943
-3.5277 -4.2176 -3.6952 -0.9022 -0.2699 0.3365
-0.4626 -3.9436 -6.7856 -0.8233 -0.5675 -0.0089
-1.5784 -0.1800 10.8848 0.4579 0.3120 0.8324
2.0552 -4.0681 -5.8410 -0.6076 -0.7942 -0.0090
4.3739 -3.7918 -4.3324 -0.3325 -0.9431 -0.0091
-4.3739 3.7918 4.3324 0.3325 0.9431 0.0091
6.2664 -3.1418 -2.4076 -0.0248 -0.9997 -0.0092
1.6981 -3.5561 7.4604 0.1417 -0.4641 0.8744
-7.5476 2.1816 0.2548 -0.2853 0.9584 0.0093

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18124
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.063
_diffrn_reflns_theta_min         5.176
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00 -33.00   0.50    0.33    -- -104.50  61.00 120.00   52
  2  ω    -22.00  30.00   0.50    0.08    --  -45.61  19.00  60.00  104
  3  ω    -20.00  29.00   0.50    0.08    --  -45.61  19.00   0.00   98
  4  ω    -21.00   4.00   0.50    0.08    --  -45.61  52.00 -89.00   50
  5  ω     30.00  87.00   0.50    0.08    --   45.61-125.00 -60.00  114
  6  ω     41.00  66.00   0.50    0.33    --  108.75-125.00-180.00   50
  7  ω     80.00 111.00   0.50    0.33    --  108.75-125.00-180.00   62
  8  ω     41.00  89.00   0.50    0.33    --  108.75-125.00-120.00   96
  9  ω     37.00  62.00   0.50    0.33    --  108.75 -95.00   0.00   50
 10  ω     56.00  82.00   0.50    0.33    --  108.75 -95.00  30.00   52
 11  ω     69.00 103.00   0.50    0.33    --  108.75 -95.00   0.00   68
 12  ω     36.00  63.00   0.50    0.33    --  108.75 -95.00  60.00   54
 13  ω     36.00  80.00   0.50    0.33    --  108.75 -95.00  90.00   88
 14  ω     59.00 101.00   0.50    0.33    --  108.75 -95.00 120.00   84
 15  ω     44.00  69.00   0.50    0.33    --  108.75-125.00  90.00   50
 16  ω     39.00  98.00   0.50    0.33    --  108.75 -95.00-120.00  118
 17  ω     37.00  98.00   0.50    0.33    --  108.75 -95.00 -90.00  122
 18  ω     74.00  99.00   0.50    0.33    --  108.75 -77.00  30.00   50
 19  ω     38.00  71.00   0.50    0.33    --  108.75 -68.00 119.81   66
 20  ω     38.00  63.00   0.50    0.33    --  108.75 -61.00  90.00   50
 21  ω     38.00  63.00   0.50    0.33    --  108.75 -52.00 125.00   50
 22  ω     46.00  71.00   0.50    0.33    --  108.75 -61.00  60.00   50
 23  ω     41.00  66.00   0.50    0.33    --  108.75 -61.00  30.00   50
 24  ω    -23.00   4.00   0.50    0.08    --   45.61 -52.00 125.00   54
 25  ω     61.00 103.00   0.50    0.33    --  108.75 -77.00 -60.00   84
 26  ω     46.00  71.00   0.50    0.33    --  108.75 -77.00-180.00   50
 27  ω    113.00 172.00   0.50    0.33    --  108.75  99.00 119.69  118
 28  ω    138.00 164.00   0.50    0.33    --  108.75 147.00 170.35   52
 29  ω    153.00 178.00   0.50    0.33    --  108.75 125.00 -90.00   50
 30  ω     88.00 114.00   0.50    0.33    --  108.75 125.00 -90.00   52
 31  ω    143.00 168.00   0.50    0.33    --  108.75 125.00-180.00   50
 32  ω     93.00 119.00   0.50    0.33    --  108.75  15.00-180.00   52
 33  ω    146.00 171.00   0.50    0.33    --  108.75  61.00-180.00   50
 34  ω     96.00 122.00   0.50    0.33    --  108.75  61.00-180.00   52
 35  ω    102.00 128.00   0.50    0.33    --  108.75  52.00 -89.00   52
 36  ω     32.00  58.00   0.50    0.08    --   45.61  52.00 -89.00   52
 37  ω     63.00 118.00   0.50    0.08    --   45.61  52.00 -89.00  110
 38  ω    142.00 167.00   0.50    0.33    --  108.75  52.00 -89.00   50
 39  ω    108.00 133.00   0.50    0.33    --  108.75  45.00 -30.00   50
 40  ω     94.00 124.00   0.50    0.33    --  108.75  45.00  30.00   60
 41  ω     93.00 174.00   0.50    0.33    --  108.75  30.00 -30.00  162
 42  ω    146.00 172.00   0.50    0.33    --  108.75  45.00  30.00   52
 43  ω    131.00 175.00   0.50    0.33    --  108.75  30.00  60.00   88
 44  ω    100.00 171.00   0.50    0.33    --  108.75  77.00 150.00  142
 45  ω    106.00 132.00   0.50    0.33    --  108.75  61.00  90.00   52
 46  ω     94.00 145.00   0.50    0.33    --  108.75  15.00  60.00  102
 47  ω    151.00 176.00   0.50    0.33    --  108.75  30.00-120.00   50
 48  ω    111.00 144.00   0.50    0.33    --  108.75  30.00-120.00   66
 49  ω    -88.00 -63.00   0.50    0.08    --  -45.61 -52.00 125.00   50
 50  ω    -59.00 -33.00   0.50    0.08    --  -45.61 -52.00 125.00   52
 51  ω   -168.00-131.00   0.50    0.33    -- -104.50 -52.00 125.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0706760000
_diffrn_orient_matrix_UB_12      0.1074020000
_diffrn_orient_matrix_UB_13      0.0540938000
_diffrn_orient_matrix_UB_21      -0.0904722000
_diffrn_orient_matrix_UB_22      0.1242418000
_diffrn_orient_matrix_UB_23      0.0175995000
_diffrn_orient_matrix_UB_31      -0.0319305000
_diffrn_orient_matrix_UB_32      -0.1143622000
_diffrn_orient_matrix_UB_33      0.0699566000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1684
_reflns_number_total             1813
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1813
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H5 of O5, All N(H) groups
 At 1.5 times of:
  H3A of O3, H4A of O4
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
3.a Riding coordinates:
 O5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5A), C6(H6)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O4(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.63188(4) 1.16153(7) 0.47784(3) 0.02356(18) Uani 1 1 d . . . . .
O1 O 0.63577(12) 0.9660(2) 0.48129(10) 0.0302(4) Uani 1 1 d . . . . .
O2 O 0.63235(14) 1.2336(2) 0.39585(10) 0.0337(4) Uani 1 1 d . . . . .
O3 O 0.72183(14) 1.2417(3) 0.52660(10) 0.0396(5) Uani 1 1 d . . . . .
H3A H 0.754454 1.310062 0.499277 0.059 Uiso 1 1 calc R U . . .
O4 O 0.53510(14) 1.2281(2) 0.52349(12) 0.0410(5) Uani 1 1 d . . . . .
H4A H 0.487243 1.159346 0.517760 0.062 Uiso 1 1 calc R U . . .
O5 O 0.63791(15) 0.5479(2) 0.35626(11) 0.0382(4) Uani 1 1 d . U . . .
H5 H 0.606658 0.457677 0.374234 0.046 Uiso 1 1 d R U . . .
O6 O 0.62121(16) 0.4251(2) 0.23880(11) 0.0435(5) Uani 1 1 d . . . . .
N1 N 0.62672(15) 1.0337(3) 0.26290(12) 0.0310(4) Uani 1 1 d . . . . .
H1 H 0.629985 1.122657 0.293281 0.037 Uiso 1 1 calc R U . . .
C1 C 0.62800(17) 0.5518(3) 0.28059(14) 0.0289(5) Uani 1 1 d . U . . .
C2 C 0.62507(16) 0.7313(3) 0.24685(14) 0.0268(5) Uani 1 1 d . . . . .
C3 C 0.61635(18) 0.7547(3) 0.16662(14) 0.0312(5) Uani 1 1 d . . . . .
H3 H 0.612585 0.658846 0.133620 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6133(2) 0.9203(3) 0.13583(15) 0.0356(6) Uani 1 1 d . . . . .
H4 H 0.607532 0.936964 0.082113 0.043 Uiso 1 1 calc R U . . .
C5 C 0.61872(19) 1.0600(3) 0.18539(15) 0.0340(5) Uani 1 1 d . . . . .
H5A H 0.616900 1.172485 0.165486 0.041 Uiso 1 1 calc R U . . .
C6 C 0.62980(17) 0.8753(3) 0.29472(14) 0.0296(5) Uani 1 1 d . . . . .
H6 H 0.635095 0.862243 0.348667 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.5065(17) . ?
P1 O2 1.5070(17) . ?
P1 O3 1.5581(17) . ?
P1 O4 1.5611(18) . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?
O5 H5 0.8598 . ?
O5 C1 1.300(3) . ?
O6 C1 1.212(3) . ?
N1 H1 0.8600 . ?
N1 C5 1.344(3) . ?
N1 C6 1.336(3) . ?
C1 C2 1.497(3) . ?
C2 C3 1.388(3) . ?
C2 C6 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(4) . ?
C5 H5A 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 113.80(10) . . ?
O1 P1 O3 110.47(10) . . ?
O1 P1 O4 109.57(10) . . ?
O2 P1 O3 110.41(10) . . ?
O2 P1 O4 110.32(11) . . ?
O3 P1 O4 101.59(11) . . ?
P1 O3 H3A 109.5 . . ?
P1 O4 H4A 109.5 . . ?
C1 O5 H5 109.2 . . ?
C5 N1 H1 118.6 . . ?
C6 N1 H1 118.6 . . ?
C6 N1 C5 122.8(2) . . ?
O5 C1 C2 114.0(2) . . ?
O6 C1 O5 125.0(2) . . ?
O6 C1 C2 120.9(2) . . ?
C3 C2 C1 120.2(2) . . ?
C6 C2 C1 120.8(2) . . ?
C6 C2 C3 119.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 119.7(2) . . ?
N1 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
N1 C6 C2 119.4(2) . . ?
N1 C6 H6 120.3 . . ?
C2 C6 H6 120.3 . . ?

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
_geom_hbond_publ_flag
O3 H3A O1 0.82 1.88 2.640(2) 152.7 8_765 yes
O4 H4A O1 0.82 1.86 2.668(2) 168.2 5_676 yes
O5 H5 O2 0.86 1.79 2.513(2) 139.7 1_545 yes
N1 H1 O2 0.86 1.95 2.745(3) 153.1 . yes
C5 H5A O6 0.93 2.31 2.954(3) 125.7 1_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C1 C2 C3 179.0(2) . . . . ?
O5 C1 C2 C6 -1.7(3) . . . . ?
O6 C1 C2 C3 -1.2(3) . . . . ?
O6 C1 C2 C6 178.1(2) . . . . ?
C1 C2 C3 C4 179.7(2) . . . . ?
C1 C2 C6 N1 -179.8(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C2 C6 N1 -0.5(3) . . . . ?
C3 C4 C5 N1 -0.2(4) . . . . ?
C5 N1 C6 C2 0.3(3) . . . . ?
C6 N1 C5 C4 0.1(4) . . . . ?
C6 C2 C3 C4 0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.670
_oxdiff_exptl_absorpt_empirical_full_min 0.588
