# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_caf-pyg
_database_code_depnum_ccdc_archive 'CCDC 2344173'
loop_
_audit_author_name
_audit_author_address
'Okba Al Rahal'
;School of Chemistry, University of Birmingham, Edgbaston, Birmingham, UK
United Kingdom
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_audit_creation_date             2024-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 N4 O2, C6 H6 O3'
_chemical_formula_sum            'C14 H16 N4 O5'
_chemical_formula_weight         320.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H16 N4 O5'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.8775(12)
_cell_length_b                   7.5913(4)
_cell_length_c                   15.0147(12)
_cell_angle_alpha                90
_cell_angle_beta                 116.937(10)
_cell_angle_gamma                90
_cell_volume                     1410.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6121
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      72.6390
_cell_measurement_theta_min      5.8470
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -3 -2 0.0432
6 3 0 0.0886
-6 4 2 0.0548
0 -5 -2 0.0532
-9 -1 6 0.0980
2 -1 -9 0.0261
-1 -3 7 0.0798
-5 1 -4 0.0573
2 -2 6 0.0714
1 3 -7 0.0343
1 5 2 0.0561
-6 4 3 0.0540
0 -5 -3 0.0493
3 3 5 0.0626
-3 2 8 0.0628

_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.105
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
7.2611 -2.8333 -2.2973 -0.4656 -0.6061 0.6449
6.4715 2.9098 -0.0099 0.2389 0.3138 0.9189
-5.9472 3.6918 2.3957 0.5463 0.7119 -0.4414
-0.0748 -4.8097 -1.7904 -0.5773 -0.7541 -0.3131
-8.7219 -0.6917 6.0766 -0.3079 0.4495 -0.8385
1.9684 -0.6941 -9.3509 0.5586 -0.8112 -0.1731
-0.9664 -3.1846 7.0660 -0.9914 0.1299 0.0147
-5.4748 1.2201 -3.8890 0.6482 -0.0839 -0.7568
2.4248 -2.4280 6.0265 -0.9010 0.1175 0.4175
0.7065 3.1450 -7.0282 0.9905 -0.1297 -0.0463
0.7588 4.6248 2.4840 0.4755 0.7760 0.4144
-5.8876 3.7215 3.3037 0.4788 0.7834 -0.3962
0.1292 -4.6843 -2.7042 -0.4943 -0.8086 -0.3193
3.4695 2.7504 4.6602 -0.0544 0.6726 0.7380
-3.3758 2.4514 8.4317 -0.1827 0.9818 0.0515

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12680
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.051
_diffrn_reflns_theta_min         3.603
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   8.00   1.00    2.50    --  -41.27 108.00 -90.00   91
  2  ω    -34.00  67.00   1.00    2.50    --   41.27 -33.00  21.00  101
  3  ω     77.00 178.00   1.00   10.00    --  102.80  33.00 179.00  101
  4  ω     27.00 109.00   1.00   10.00    --  102.80-108.00 171.00   82
  5  ω    104.00 178.00   1.00   10.00    --  102.80  95.00  10.00   74
  6  ω   -116.00 -17.00   1.00    2.50    --  -41.27 -38.00-180.00   99
  7  ω      6.00  81.00   1.00    2.50    --   41.27 -99.00 120.00   75
  8  ω     61.00 146.00   1.00   10.00    --  102.80 178.00   0.00   85
  9  ω    103.00 178.00   1.00   10.00    --  102.80  77.00-120.00   75
 10  ω     77.00 176.00   1.00   10.00    --  102.80  45.00   0.00   99
 11  ω    104.00 176.00   1.00   10.00    --  102.80 111.00 -90.00   72
 12  ω     20.00 107.00   1.00   10.00    --  102.80 -94.00   0.00   87
 13  ω   -113.00 -13.00   1.00    2.50    --  -41.27 -57.00  60.00  100
 14  ω   -113.00 -13.00   1.00    2.50    --  -41.27 -57.00 150.00  100
 15  ω   -113.00 -13.00   1.00    2.50    --  -41.27 -57.00 -60.00  100
 16  ω     74.00 156.00   1.00   10.00    --  102.80  61.00-150.00   82
 17  ω     74.00 175.00   1.00   10.00    --  102.80  61.00  90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0303110000
_diffrn_orient_matrix_UB_12      0.1492415000
_diffrn_orient_matrix_UB_13      -0.0771908000
_diffrn_orient_matrix_UB_21      -0.0093640000
_diffrn_orient_matrix_UB_22      0.1289331000
_diffrn_orient_matrix_UB_23      0.0752098000
_diffrn_orient_matrix_UB_31      0.1203752000
_diffrn_orient_matrix_UB_32      0.0482284000
_diffrn_orient_matrix_UB_33      0.0402754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2275
_reflns_number_total             2730
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.070
_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)+(0.0634P)²+0.5286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1310
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C)
;
_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
C1 C 0.7313(2) 0.4310(3) 0.32917(16) 0.0353(5) Uani 1 1 d . . . . .
H1A H 0.790014 0.484650 0.319266 0.053 Uiso 1 1 calc R U . . .
H1B H 0.661986 0.480103 0.280699 0.053 Uiso 1 1 calc R U . . .
H1C H 0.731405 0.303300 0.319650 0.053 Uiso 1 1 calc R U . . .
C2 C 0.84461(16) 0.4277(2) 0.50920(15) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.96683(16) 0.4395(3) 0.68680(16) 0.0293(5) Uani 1 1 d . . . . .
H3A H 0.968607 0.317745 0.709180 0.044 Uiso 1 1 calc R U . . .
H3B H 0.981152 0.520152 0.742376 0.044 Uiso 1 1 calc R U . . .
H3C H 1.022135 0.455268 0.663913 0.044 Uiso 1 1 calc R U . . .
C4 C 0.78430(15) 0.5617(2) 0.62783(14) 0.0212(4) Uani 1 1 d . . . . .
C5 C 0.68687(15) 0.6009(2) 0.54080(14) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.57101(19) 0.7690(3) 0.60453(17) 0.0331(5) Uani 1 1 d . . . . .
H6A H 0.566492 0.677284 0.648421 0.050 Uiso 1 1 calc R U . . .
H6B H 0.502128 0.832436 0.572542 0.050 Uiso 1 1 calc R U . . .
H6C H 0.629010 0.851626 0.643990 0.050 Uiso 1 1 calc R U . . .
C8 C 0.52888(16) 0.6900(3) 0.42933(16) 0.0280(4) Uani 1 1 d . . . . .
H8 H 0.459180 0.742527 0.400078 0.034 Uiso 1 1 calc R U . . .
C10 C 0.67028(16) 0.5564(2) 0.44647(14) 0.0218(4) Uani 1 1 d . . . . .
N1 N 0.74717(13) 0.4681(2) 0.43013(12) 0.0233(4) Uani 1 1 d . . . . .
N2 N 0.86022(13) 0.4774(2) 0.60457(12) 0.0221(4) Uani 1 1 d . . . . .
N3 N 0.59390(13) 0.6881(2) 0.52814(13) 0.0248(4) Uani 1 1 d . . . . .
N4 N 0.57222(14) 0.6100(2) 0.37570(13) 0.0272(4) Uani 1 1 d . . . . .
O1 O 0.91605(12) 0.35245(19) 0.49738(11) 0.0305(4) Uani 1 1 d . . . . .
O2 O 0.80480(12) 0.5956(2) 0.71488(10) 0.0308(4) Uani 1 1 d . . . . .
C11 C 1.08546(15) 0.1073(2) 0.43704(14) 0.0207(4) Uani 1 1 d . . . . .
C12 C 1.13947(15) 0.0199(2) 0.39105(14) 0.0207(4) Uani 1 1 d . . . . .
C13 C 1.24289(15) -0.0450(2) 0.44876(14) 0.0217(4) Uani 1 1 d . . . . .
C14 C 1.29345(16) -0.0219(3) 0.55114(15) 0.0264(4) Uani 1 1 d . . . . .
H14 H 1.364129 -0.066948 0.590413 0.032 Uiso 1 1 calc R U . . .
C15 C 1.23973(18) 0.0678(3) 0.59592(15) 0.0308(5) Uani 1 1 d . . . . .
H15 H 1.274697 0.085902 0.666136 0.037 Uiso 1 1 calc R U . . .
C16 C 1.13591(17) 0.1313(3) 0.53978(15) 0.0256(4) Uani 1 1 d . . . . .
H16 H 1.099522 0.190891 0.571410 0.031 Uiso 1 1 calc R U . . .
O3 O 0.98340(11) 0.16665(19) 0.37580(11) 0.0265(3) Uani 1 1 d . . . . .
H3 H 0.958(2) 0.226(4) 0.417(2) 0.049(8) Uiso 1 1 d . . . . .
O4 O 1.09592(12) -0.0105(2) 0.29115(10) 0.0279(3) Uani 1 1 d . . . . .
H4 H 1.039(3) 0.047(4) 0.257(2) 0.047(8) Uiso 1 1 d . . . . .
O5 O 1.29642(11) -0.13356(19) 0.40429(11) 0.0266(3) Uani 1 1 d . . . . .
H5 H 1.259(3) -0.116(4) 0.338(3) 0.059(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 N1 1.457(2) . ?
C2 N1 1.370(3) . ?
C2 N2 1.399(2) . ?
C2 O1 1.225(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 N2 1.463(3) . ?
C4 C5 1.422(3) . ?
C4 N2 1.405(2) . ?
C4 O2 1.232(2) . ?
C5 C10 1.370(3) . ?
C5 N3 1.385(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 N3 1.457(3) . ?
C8 H8 0.9500 . ?
C8 N3 1.343(3) . ?
C8 N4 1.348(3) . ?
C10 N1 1.373(3) . ?
C10 N4 1.355(3) . ?
C11 C12 1.396(3) . ?
C11 C16 1.387(3) . ?
C11 O3 1.369(2) . ?
C12 C13 1.388(3) . ?
C12 O4 1.359(2) . ?
C13 C14 1.382(3) . ?
C13 O5 1.378(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
O3 H3 0.95(3) . ?
O4 H4 0.84(3) . ?
O5 H5 0.89(3) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
N1 C2 N2 117.44(17) . . ?
O1 C2 N1 121.65(18) . . ?
O1 C2 N2 120.90(18) . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
N2 C4 C5 112.00(16) . . ?
O2 C4 C5 126.68(18) . . ?
O2 C4 N2 121.32(18) . . ?
C10 C5 C4 122.87(18) . . ?
C10 C5 N3 105.44(17) . . ?
N3 C5 C4 131.67(18) . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
N3 C8 H8 123.3 . . ?
N3 C8 N4 113.38(18) . . ?
N4 C8 H8 123.3 . . ?
C5 C10 N1 121.65(18) . . ?
N4 C10 C5 112.04(17) . . ?
N4 C10 N1 126.31(17) . . ?
C2 N1 C1 118.85(17) . . ?
C2 N1 C10 119.75(16) . . ?
C10 N1 C1 121.14(17) . . ?
C2 N2 C3 116.05(16) . . ?
C2 N2 C4 126.22(16) . . ?
C4 N2 C3 117.72(16) . . ?
C5 N3 C6 127.97(18) . . ?
C8 N3 C5 105.94(17) . . ?
C8 N3 C6 126.04(18) . . ?
C8 N4 C10 103.19(17) . . ?
C16 C11 C12 119.92(17) . . ?
O3 C11 C12 116.63(17) . . ?
O3 C11 C16 123.45(18) . . ?
C13 C12 C11 119.69(17) . . ?
O4 C12 C11 123.83(17) . . ?
O4 C12 C13 116.47(17) . . ?
C14 C13 C12 120.65(18) . . ?
O5 C13 C12 120.17(17) . . ?
O5 C13 C14 119.18(17) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.20(18) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.00(19) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.53(19) . . ?
C15 C16 H16 120.2 . . ?
C11 O3 H3 107.3(18) . . ?
C12 O4 H4 114(2) . . ?
C13 O5 H5 107(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
_geom_hbond_publ_flag
O3 H3 O1 0.95(3) 1.83(3) 2.782(2) 176(3) . yes
O4 H4 N4 0.84(3) 1.95(3) 2.695(2) 147(3) 2_645 yes
O5 H5 O2 0.89(3) 2.22(3) 2.913(2) 134(3) 4_665 yes
O5 H5 O4 0.89(3) 2.19(3) 2.687(2) 114(3) . 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
C4 C5 C10 N1 0.9(3) . . . . ?
C4 C5 C10 N4 -178.96(17) . . . . ?
C4 C5 N3 C6 1.0(3) . . . . ?
C4 C5 N3 C8 178.6(2) . . . . ?
C5 C4 N2 C2 -2.6(3) . . . . ?
C5 C4 N2 C3 176.22(16) . . . . ?
C5 C10 N1 C1 -176.22(18) . . . . ?
C5 C10 N1 C2 -2.1(3) . . . . ?
C5 C10 N4 C8 0.3(2) . . . . ?
C10 C5 N3 C6 -177.53(19) . . . . ?
C10 C5 N3 C8 0.2(2) . . . . ?
N1 C2 N2 C3 -177.30(16) . . . . ?
N1 C2 N2 C4 1.6(3) . . . . ?
N1 C10 N4 C8 -179.52(19) . . . . ?
N2 C2 N1 C1 175.18(17) . . . . ?
N2 C2 N1 C10 1.0(3) . . . . ?
N2 C4 C5 C10 1.4(3) . . . . ?
N2 C4 C5 N3 -176.89(18) . . . . ?
N3 C5 C10 N1 179.54(17) . . . . ?
N3 C5 C10 N4 -0.3(2) . . . . ?
N3 C8 N4 C10 -0.2(2) . . . . ?
N4 C8 N3 C5 0.0(2) . . . . ?
N4 C8 N3 C6 177.78(18) . . . . ?
N4 C10 N1 C1 3.6(3) . . . . ?
N4 C10 N1 C2 177.69(18) . . . . ?
O1 C2 N1 C1 -4.2(3) . . . . ?
O1 C2 N1 C10 -178.44(18) . . . . ?
O1 C2 N2 C3 2.1(3) . . . . ?
O1 C2 N2 C4 -179.03(17) . . . . ?
O2 C4 C5 C10 -179.21(18) . . . . ?
O2 C4 C5 N3 2.5(3) . . . . ?
O2 C4 N2 C2 177.90(17) . . . . ?
O2 C4 N2 C3 -3.2(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C11 C12 C13 O5 179.17(16) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C14 C15 C16 C11 -1.0(3) . . . . ?
C16 C11 C12 C13 1.0(3) . . . . ?
C16 C11 C12 O4 179.48(17) . . . . ?
O3 C11 C12 C13 -179.46(16) . . . . ?
O3 C11 C12 O4 -1.0(3) . . . . ?
O3 C11 C16 C15 -179.58(18) . . . . ?
O4 C12 C13 C14 -179.43(17) . . . . ?
O4 C12 C13 O5 0.6(3) . . . . ?
O5 C13 C14 C15 179.75(18) . . . . ?

_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 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.870
####################################################################### 
# 
# 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_caf-pyg-4H2O
_database_code_depnum_ccdc_archive 'CCDC 2344174'
loop_
_audit_author_name
_audit_author_address
'Okba Al Rahal'
;School of Chemistry, University of Birmingham, Edgbaston, Birmingham, UK
United Kingdom
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_audit_creation_date             2024-04-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 N4 O2, C6 H6 O3, 4(H2 O)'
_chemical_formula_sum            'C14 H24 N4 O9'
_chemical_formula_weight         392.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   23.1123(5)
_cell_length_b                   23.1123(5)
_cell_length_c                   6.8449(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3656.40(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6810
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.9950
_cell_measurement_theta_min      5.3890
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.664
_exptl_absorpt_coefficient_mu    1.029
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -12 0 0.0281
4 2 4 0.2208
-8 13 0 0.0323
11 2 3 0.1730
6 11 3 0.1576
4 -14 0 0.0323
-5 -14 -1 0.0372
0 15 0 0.0426
-8 -13 1 0.0506
-15 0 0 0.0314
15 3 0 0.0417
0 -4 4 0.2091
-8 13 0 0.0293
9 7 -3 0.1495
10 11 1 0.0680
3 7 -4 0.1864
-1 3 -4 0.1978

_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.098
_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
9.0263 -11.9872 -0.0276 -0.0479 -0.2059 -0.9774
4.4724 1.8390 4.2039 -0.0756 0.9583 -0.2755
-8.0890 12.6325 0.1186 -0.0207 0.2435 0.9697
11.0611 1.8895 2.9471 -0.4984 0.7253 -0.4749
5.5034 10.9434 2.5633 -0.5517 0.8011 0.2323
4.0572 -14.4452 -0.0537 0.3056 -0.2879 -0.9076
-4.5223 -14.1636 -0.5955 0.7241 -0.4423 -0.5292
-0.0186 15.0013 0.0937 -0.5395 0.3289 0.7751
-7.7200 -12.5507 0.8397 0.9150 -0.1194 -0.3855
-14.9983 -0.2738 -0.1069 0.8055 -0.1063 0.5829
14.6932 3.0270 -0.0941 -0.9004 0.1185 -0.4187
-0.1146 -4.1796 4.2661 0.3918 0.8238 -0.4096
-7.9594 12.7205 -0.0267 -0.0388 0.2150 0.9758
9.2958 7.3925 -2.7161 -0.9143 -0.3792 0.1423
10.0618 10.8724 0.7029 -0.8946 0.4262 0.1346
3.1915 6.8235 -3.8423 -0.6291 -0.6630 0.4058
-0.7073 2.9678 -4.3490 -0.3083 -0.8708 0.3830

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19300
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.311
_diffrn_reflns_theta_min         3.825
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  31.00   1.00    4.79    --  -41.27  51.00  43.00   99
  2  ω    101.00 178.00   1.00   19.16    --  112.00  72.00-120.00   77
  3  ω     39.00 109.00   1.00   19.16    --  112.00-111.00  28.00   70
  4  ω      6.00  81.00   1.00    4.79    --   41.27 -99.00-150.00   75
  5  ω     17.00 116.00   1.00    4.79    --   41.27  38.00-120.00   99
  6  ω    103.00 178.00   1.00   19.16    --  112.00  77.00   0.00   75
  7  ω     39.00 138.00   1.00   19.16    --  112.00 -45.00 -60.00   99
  8  ω    104.00 178.00   1.00   19.16    --  112.00 111.00 -30.00   74
  9  ω    104.00 178.00   1.00   19.16    --  112.00 111.00 122.00   74
 10  ω     13.00 114.00   1.00    4.79    --   41.27  57.00 120.00  101
 11  ω     13.00  38.00   1.00    4.79    --   41.27  57.00 -60.00   25
 12  ω     13.00 114.00   1.00    4.79    --   41.27  57.00   0.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0534345000
_diffrn_orient_matrix_UB_12      -0.0363685000
_diffrn_orient_matrix_UB_13      0.0547683000
_diffrn_orient_matrix_UB_21      0.0051912000
_diffrn_orient_matrix_UB_22      0.0205964000
_diffrn_orient_matrix_UB_23      0.2134320000
_diffrn_orient_matrix_UB_31      -0.0394854000
_diffrn_orient_matrix_UB_32      0.0519108000
_diffrn_orient_matrix_UB_33      -0.0462257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2998
_reflns_number_total             3825
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.056
_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)+(0.0476P)²+2.7291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O9-H9B
 0.95 with sigma of 0.02
 O9A-H9AA
 0.95 with sigma of 0.02
3. Others
 Sof(O9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(1)
 Sof(O9)=Sof(H9A)=Sof(H9B)=FVAR(1)
4.a Free rotating group:
 O6(H6D,H6E), O7(H7A,H7B), O8(H8A,H8B), O9(H9A,H9B), O9A(H9AA,H9AB)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C14(H14)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C)
;
_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
C1 C 0.68400(9) 0.42053(9) 0.6130(3) 0.0300(4) Uani 1 1 d . . . . .
H1A H 0.695662 0.416855 0.475867 0.045 Uiso 1 1 calc R U . . .
H1B H 0.667345 0.383869 0.657842 0.045 Uiso 1 1 calc R U . . .
H1C H 0.717892 0.430048 0.692763 0.045 Uiso 1 1 calc R U . . .
C2 C 0.58498(9) 0.45951(8) 0.6808(3) 0.0251(4) Uani 1 1 d . . . . .
H2 H 0.568047 0.422982 0.708761 0.030 Uiso 1 1 calc R U . . .
C3 C 0.59560(8) 0.54960(8) 0.6396(3) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.53073(8) 0.63432(9) 0.6628(3) 0.0294(5) Uani 1 1 d . . . . .
H4A H 0.511198 0.641259 0.537946 0.044 Uiso 1 1 calc R U . . .
H4B H 0.535668 0.671109 0.732049 0.044 Uiso 1 1 calc R U . . .
H4C H 0.507336 0.608007 0.742606 0.044 Uiso 1 1 calc R U . . .
C5 C 0.63286(8) 0.64306(8) 0.5768(3) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.73477(9) 0.65527(10) 0.4937(4) 0.0302(5) Uani 1 1 d . . . . .
H6A H 0.7514(12) 0.6445(12) 0.367(4) 0.045 Uiso 1 1 d . U . . .
H6B H 0.7661(12) 0.6496(12) 0.588(4) 0.045 Uiso 1 1 d . U . . .
H6C H 0.7223(14) 0.6941(14) 0.480(5) 0.063(9) Uiso 1 1 d . . . . .
C7 C 0.69822(8) 0.55763(8) 0.5524(3) 0.0211(4) Uani 1 1 d . . . . .
C8 C 0.64867(8) 0.52493(8) 0.6042(3) 0.0190(4) Uani 1 1 d . . . . .
N1 N 0.64115(7) 0.46621(7) 0.6313(2) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.55528(7) 0.50961(7) 0.6868(2) 0.0232(3) Uani 1 1 d . . . . .
N3 N 0.58744(6) 0.60833(7) 0.6269(2) 0.0198(3) Uani 1 1 d . . . . .
N4 N 0.68638(7) 0.61726(7) 0.5463(2) 0.0212(3) Uani 1 1 d . . . . .
O1 O 0.74725(6) 0.53975(6) 0.5158(2) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.62727(6) 0.69586(6) 0.5605(2) 0.0272(3) Uani 1 1 d . . . . .
C9 C 0.51428(8) 0.90922(8) 0.3474(3) 0.0212(4) Uani 1 1 d . . . . .
C10 C 0.50327(8) 0.85140(8) 0.3905(3) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.54872(8) 0.81452(8) 0.4366(3) 0.0209(4) Uani 1 1 d . . . . .
C12 C 0.60535(8) 0.83488(8) 0.4390(3) 0.0225(4) Uani 1 1 d . . . . .
H12 H 0.636457 0.809639 0.470106 0.027 Uiso 1 1 calc R U . . .
C13 C 0.61574(8) 0.89252(8) 0.3954(3) 0.0236(4) Uani 1 1 d . . . . .
H13 H 0.654323 0.906682 0.396163 0.028 Uiso 1 1 calc R U . . .
C14 C 0.57069(8) 0.92976(8) 0.3506(3) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.578392 0.969249 0.322103 0.028 Uiso 1 1 calc R U . . .
O3 O 0.46743(6) 0.94261(6) 0.3044(2) 0.0293(3) Uani 1 1 d . . . . .
H3 H 0.4777(13) 0.9789(13) 0.266(4) 0.055(9) Uiso 1 1 d . . . . .
O4 O 0.44720(6) 0.83172(6) 0.3872(2) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.4450(16) 0.7957(16) 0.414(5) 0.081(12) Uiso 1 1 d . . . . .
O5 O 0.53326(6) 0.75911(6) 0.4784(2) 0.0288(3) Uani 1 1 d . . . . .
H5 H 0.5626(14) 0.7411(14) 0.511(5) 0.055(9) Uiso 1 1 d . . . . .
O6 O 0.82360(7) 0.45646(7) 0.3521(2) 0.0374(4) Uani 1 1 d G . . . .
H6D H 0.808100 0.439429 0.251476 0.056 Uiso 1 1 d G U . . .
H6E H 0.798946 0.483227 0.384100 0.056 Uiso 1 1 d G U . . .
O7 O 0.61365(8) 0.33884(6) 0.1783(2) 0.0360(4) Uani 1 1 d G . . . .
H7A H 0.590296 0.334598 0.079522 0.054 Uiso 1 1 d G U . . .
H7B H 0.620117 0.375898 0.183627 0.054 Uiso 1 1 d G U . . .
O8 O 0.77865(7) 0.40044(7) 1.0289(2) 0.0361(4) Uani 1 1 d G . . . .
H8A H 0.799327 0.400761 0.922634 0.054 Uiso 1 1 d G U . . .
H8B H 0.765089 0.365388 1.035543 0.054 Uiso 1 1 d G U . . .
O9 O 0.73432(15) 0.30613(16) 1.1843(6) 0.0409(11) Uani 0.494(5) 1 d DG . P A 1
H9A H 0.694979 0.318899 1.218240 0.061 Uiso 0.494(5) 1 d G U P A 1
H9B H 0.758580 0.301837 1.295397 0.061 Uiso 0.494(5) 1 d DG U P A 1
O9A O 0.71417(15) 0.29207(15) 1.0328(5) 0.0415(11) Uani 0.506(5) 1 d DG . P A 2
H9AA H 0.681309 0.297794 1.114906 0.062 Uiso 0.506(5) 1 d DG U P A 2
H9AB H 0.730339 0.267834 1.113335 0.062 Uiso 0.506(5) 1 d G 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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 N1 1.453(2) . ?
C2 H2 0.9500 . ?
C2 N1 1.351(3) . ?
C2 N2 1.347(3) . ?
C3 C8 1.374(3) . ?
C3 N2 1.352(2) . ?
C3 N3 1.373(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N3 1.463(2) . ?
C5 N3 1.365(2) . ?
C5 N4 1.389(2) . ?
C5 O2 1.232(2) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.98(3) . ?
C6 H6C 0.95(3) . ?
C6 N4 1.467(3) . ?
C7 C8 1.417(3) . ?
C7 N4 1.406(2) . ?
C7 O1 1.232(2) . ?
C8 N1 1.381(2) . ?
C9 C10 1.392(3) . ?
C9 C14 1.388(3) . ?
C9 O3 1.362(2) . ?
C10 C11 1.389(3) . ?
C10 O4 1.374(2) . ?
C11 C12 1.391(3) . ?
C11 O5 1.360(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
O3 H3 0.91(3) . ?
O4 H4 0.86(4) . ?
O5 H5 0.83(3) . ?
O6 H6D 0.8707 . ?
O6 H6E 0.8691 . ?
O7 H7A 0.8704 . ?
O7 H7B 0.8703 . ?
O8 H8A 0.8704 . ?
O8 H8B 0.8698 . ?
O9 H9A 0.9838 . ?
O9 H9B 0.9502 . ?
O9A H9AA 0.9539 . ?
O9A H9AB 0.8701 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
N1 C2 H2 123.2 . . ?
N2 C2 H2 123.2 . . ?
N2 C2 N1 113.51(17) . . ?
N2 C3 C8 111.95(17) . . ?
N2 C3 N3 126.61(17) . . ?
N3 C3 C8 121.44(17) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
N3 C5 N4 118.04(16) . . ?
O2 C5 N3 121.63(17) . . ?
O2 C5 N4 120.33(17) . . ?
H6A C6 H6B 105(2) . . ?
H6A C6 H6C 106(2) . . ?
H6B C6 H6C 115(2) . . ?
N4 C6 H6A 111.3(16) . . ?
N4 C6 H6B 108.7(16) . . ?
N4 C6 H6C 111.0(19) . . ?
N4 C7 C8 111.89(16) . . ?
O1 C7 C8 127.97(18) . . ?
O1 C7 N4 120.13(17) . . ?
C3 C8 C7 122.96(17) . . ?
C3 C8 N1 105.77(16) . . ?
N1 C8 C7 131.26(17) . . ?
C2 N1 C1 126.41(17) . . ?
C2 N1 C8 105.50(15) . . ?
C8 N1 C1 128.08(17) . . ?
C2 N2 C3 103.26(16) . . ?
C3 N3 C4 121.22(15) . . ?
C5 N3 C3 119.44(15) . . ?
C5 N3 C4 119.33(16) . . ?
C5 N4 C6 117.31(16) . . ?
C5 N4 C7 126.15(16) . . ?
C7 N4 C6 116.48(16) . . ?
C14 C9 C10 119.81(17) . . ?
O3 C9 C10 116.38(17) . . ?
O3 C9 C14 123.81(17) . . ?
C11 C10 C9 119.92(17) . . ?
O4 C10 C9 119.14(16) . . ?
O4 C10 C11 120.94(16) . . ?
C10 C11 C12 120.46(17) . . ?
O5 C11 C10 115.26(17) . . ?
O5 C11 C12 124.28(17) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.04(17) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.98(18) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.79(18) . . ?
C13 C14 H14 120.1 . . ?
C9 O3 H3 112.1(19) . . ?
C10 O4 H4 112(3) . . ?
C11 O5 H5 108(2) . . ?
H6D O6 H6E 104.5 . . ?
H7A O7 H7B 104.5 . . ?
H8A O8 H8B 104.4 . . ?
H9A O9 H9B 112.8 . . ?
H9AA O9A H9AB 93.3 . . ?

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 H3 N2 0.91(3) 1.87(3) 2.777(2) 174(3) 3_654 yes
O4 H4 O5 0.86(4) 2.25(4) 2.676(2) 111(3) . yes
O4 H4 O8 0.86(4) 2.04(4) 2.829(2) 153(3) 7_577 yes
O5 H5 O2 0.83(3) 1.86(3) 2.678(2) 174(3) . 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
C3 C8 N1 C1 -179.65(18) . . . . ?
C3 C8 N1 C2 -0.1(2) . . . . ?
C7 C8 N1 C1 0.0(3) . . . . ?
C7 C8 N1 C2 179.54(19) . . . . ?
C8 C3 N2 C2 0.4(2) . . . . ?
C8 C3 N3 C4 179.39(18) . . . . ?
C8 C3 N3 C5 0.4(3) . . . . ?
C8 C7 N4 C5 -3.0(3) . . . . ?
C8 C7 N4 C6 -179.93(17) . . . . ?
N1 C2 N2 C3 -0.5(2) . . . . ?
N2 C2 N1 C1 179.92(18) . . . . ?
N2 C2 N1 C8 0.4(2) . . . . ?
N2 C3 C8 C7 -179.86(17) . . . . ?
N2 C3 C8 N1 -0.2(2) . . . . ?
N2 C3 N3 C4 -0.9(3) . . . . ?
N2 C3 N3 C5 -179.87(18) . . . . ?
N3 C3 C8 C7 -0.1(3) . . . . ?
N3 C3 C8 N1 179.57(16) . . . . ?
N3 C3 N2 C2 -179.35(18) . . . . ?
N3 C5 N4 C6 -179.64(18) . . . . ?
N3 C5 N4 C7 3.4(3) . . . . ?
N4 C5 N3 C3 -1.9(3) . . . . ?
N4 C5 N3 C4 179.09(17) . . . . ?
N4 C7 C8 C3 1.2(2) . . . . ?
N4 C7 C8 N1 -178.35(18) . . . . ?
O1 C7 C8 C3 -179.12(19) . . . . ?
O1 C7 C8 N1 1.3(3) . . . . ?
O1 C7 N4 C5 177.37(18) . . . . ?
O1 C7 N4 C6 0.4(3) . . . . ?
O2 C5 N3 C3 178.78(18) . . . . ?
O2 C5 N3 C4 -0.2(3) . . . . ?
O2 C5 N4 C6 -0.3(3) . . . . ?
O2 C5 N4 C7 -177.26(18) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C9 C10 C11 O5 179.32(17) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C9 -0.6(3) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
C14 C9 C10 O4 179.87(17) . . . . ?
O3 C9 C10 C11 -179.76(17) . . . . ?
O3 C9 C10 O4 0.1(3) . . . . ?
O3 C9 C14 C13 -179.79(18) . . . . ?
O4 C10 C11 C12 179.82(17) . . . . ?
O4 C10 C11 O5 -0.5(3) . . . . ?
O5 C11 C12 C13 -179.45(18) . . . . ?

_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 1.827
_oxdiff_exptl_absorpt_empirical_full_min 0.663
