# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2026

####################################################################### 
# 
# 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_exp_2052_auto
_database_code_depnum_ccdc_archive 'CCDC 2533641'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda-Raj Olga Ksiazkiewicz'
;Department of Physical Chemistry, Faculty of Chemistry, University of Lodz
Poland
;
_audit_update_record             
;
2026-02-26 deposited with the CCDC.	2026-06-09 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         'C7 H4 N O4, C4 H5 N3 O, C4 H6 N3 O, H2 O'
_chemical_formula_sum            'C15 H17 N7 O7'
_chemical_formula_weight         407.35

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6543(2)
_cell_length_b                   7.3960(3)
_cell_length_c                   19.1733(6)
_cell_angle_alpha                86.316(3)
_cell_angle_beta                 87.762(2)
_cell_angle_gamma                66.189(3)
_cell_volume                     861.43(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(6)
_cell_measurement_reflns_used    15062
_cell_measurement_theta_min      4.5730
_cell_measurement_theta_max      75.6210

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    1.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(6)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28167
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.623
_diffrn_reflns_theta_max         76.494
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3349
_reflns_number_gt                3000
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0729P)²+0.2726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3349
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.26891(15) -0.34062(14) 0.10692(5) 0.0223(2) Uani 1 1 d . . . . .
O7 O 0.76223(15) -0.28720(13) 0.05170(5) 0.0226(2) Uani 1 1 d . . . . .
O25 O 0.21265(16) 0.50208(14) 0.29267(5) 0.0254(2) Uani 1 1 d . . . . .
O13 O -0.19554(17) 0.54837(15) 0.24264(5) 0.0256(2) Uani 1 1 d . . . . .
O24 O 0.51678(17) 0.49823(18) 0.33892(5) 0.0350(3) Uani 1 1 d . . . . .
N6 N 0.24796(17) -0.02485(16) 0.10255(5) 0.0183(2) Uani 1 1 d . . . . .
N12 N 0.74475(17) 0.02647(16) 0.04590(6) 0.0184(2) Uani 1 1 d . . . . .
N8 N 0.75627(17) -0.13998(16) 0.15336(6) 0.0201(2) Uani 1 1 d . . . . .
H8 H 0.763873 -0.245722 0.178876 0.024 Uiso 1 1 calc R U . . .
N2 N 0.26831(18) -0.20633(17) 0.20953(6) 0.0205(2) Uani 1 1 d . . . . .
H2 H 0.275476 -0.315927 0.232271 0.025 Uiso 1 1 calc R U . . .
N11 N 0.73106(18) 0.34175(16) 0.03594(6) 0.0215(2) Uani 1 1 d . . . . .
H11A H 0.733074 0.335437 -0.009777 0.026 Uiso 1 1 calc R U . . .
H11B H 0.725545 0.449609 0.054380 0.026 Uiso 1 1 calc R U . . .
O21 O 0.0136(2) 0.08913(19) 0.60856(6) 0.0437(3) Uani 1 1 d . . . . .
O22 O 0.3165(2) 0.08183(19) 0.64871(6) 0.0439(3) Uani 1 1 d . . . . .
N5 N 0.21583(18) 0.29512(17) 0.10214(6) 0.0214(2) Uani 1 1 d . . . . .
H5A H 0.209142 0.300745 0.056262 0.026 Uiso 1 1 calc R U . . .
H5B H 0.208303 0.399071 0.123806 0.026 Uiso 1 1 calc R U . . .
N20 N 0.1824(2) 0.11863(19) 0.60215(6) 0.0319(3) Uani 1 1 d . . . . .
C5 C 0.2373(2) 0.12944(19) 0.13876(7) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.7550(2) -0.1435(2) 0.08252(7) 0.0194(3) Uani 1 1 d . . . . .
C1 C 0.2624(2) -0.19393(19) 0.13800(7) 0.0185(3) Uani 1 1 d . . . . .
C11 C 0.7362(2) 0.19116(19) 0.07637(7) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.2487(2) 0.1175(2) 0.21306(7) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.245952 0.225308 0.238082 0.025 Uiso 1 1 calc R U . . .
C10 C 0.7349(2) 0.1884(2) 0.15067(7) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.726345 0.300360 0.174297 0.025 Uiso 1 1 calc R U . . .
C9 C 0.7461(2) 0.0222(2) 0.18627(7) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.746986 0.017241 0.235897 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2634(2) -0.0533(2) 0.24619(7) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.270428 -0.067011 0.295749 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1233(2) 0.3154(2) 0.41693(7) 0.0253(3) Uani 1 1 d . . . . .
H16 H 0.026560 0.338740 0.379045 0.030 Uiso 1 1 calc R U . . .
C14 C 0.2263(2) 0.2021(2) 0.53453(7) 0.0250(3) Uani 1 1 d . . . . .
C23 C 0.3501(2) 0.4610(2) 0.34121(7) 0.0232(3) Uani 1 1 d . . . . .
C19 C 0.4100(2) 0.2452(2) 0.52798(7) 0.0267(3) Uani 1 1 d . . . . .
H19 H 0.506617 0.221005 0.565952 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3054(2) 0.3632(2) 0.40867(7) 0.0221(3) Uani 1 1 d . . . . .
C18 C 0.4482(2) 0.3249(2) 0.46405(7) 0.0248(3) Uani 1 1 d . . . . .
H18 H 0.574582 0.354023 0.457915 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0830(2) 0.2339(2) 0.48023(8) 0.0265(3) Uani 1 1 d . . . . .
H15 H -0.040584 0.200610 0.486228 0.032 Uiso 1 1 calc R U . . .
H12 H 0.743(3) 0.025(2) -0.0014(10) 0.025(4) Uiso 1 1 d . . . . .
H13A H -0.298(4) 0.540(3) 0.2747(13) 0.057(6) Uiso 1 1 d . . . . .
H13B H -0.075(4) 0.527(3) 0.2669(11) 0.046(5) 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
O1 C1 1.2558(15) . ?
O7 C7 1.2324(16) . ?
O25 C23 1.2653(17) . ?
O13 H13A 0.92(3) . ?
O13 H13B 0.89(2) . ?
O24 C23 1.2446(17) . ?
N6 C5 1.3498(16) . ?
N6 C1 1.3543(17) . ?
N12 C11 1.3644(17) . ?
N12 C7 1.3777(17) . ?
N12 H12 0.907(19) . ?
N8 C7 1.3606(17) . ?
N8 C9 1.3677(17) . ?
N8 H8 0.8800 . ?
N2 C3 1.3593(17) . ?
N2 C1 1.3696(17) . ?
N2 H2 0.8800 . ?
N11 C11 1.3049(18) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
O21 N20 1.2279(18) . ?
O22 N20 1.2258(18) . ?
N5 C5 1.3307(17) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N20 C14 1.4699(18) . ?
C5 C4 1.4248(19) . ?
C11 C10 1.4230(18) . ?
C4 C3 1.346(2) . ?
C4 H4 0.9500 . ?
C10 C9 1.343(2) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C3 H3 0.9500 . ?
C16 C15 1.385(2) . ?
C16 C17 1.3937(19) . ?
C16 H16 0.9500 . ?
C14 C19 1.382(2) . ?
C14 C15 1.383(2) . ?
C23 C17 1.5194(19) . ?
C19 C18 1.385(2) . ?
C19 H19 0.9500 . ?
C17 C18 1.3904(19) . ?
C18 H18 0.9500 . ?
C15 H15 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
H13A O13 H13B 106.2(19) . . ?
C5 N6 C1 119.04(11) . . ?
C11 N12 C7 124.12(11) . . ?
C11 N12 H12 119.9(11) . . ?
C7 N12 H12 116.0(11) . . ?
C7 N8 C9 122.25(12) . . ?
C7 N8 H8 118.9 . . ?
C9 N8 H8 118.9 . . ?
C3 N2 C1 121.52(11) . . ?
C3 N2 H2 119.2 . . ?
C1 N2 H2 119.2 . . ?
C11 N11 H11A 120.0 . . ?
C11 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O22 N20 O21 123.84(13) . . ?
O22 N20 C14 118.20(13) . . ?
O21 N20 C14 117.96(13) . . ?
N5 C5 N6 117.21(12) . . ?
N5 C5 C4 120.78(12) . . ?
N6 C5 C4 122.00(12) . . ?
O7 C7 N8 123.43(12) . . ?
O7 C7 N12 120.84(12) . . ?
N8 C7 N12 115.73(11) . . ?
O1 C1 N6 121.60(11) . . ?
O1 C1 N2 118.69(12) . . ?
N6 C1 N2 119.70(11) . . ?
N11 C11 N12 118.34(12) . . ?
N11 C11 C10 123.67(12) . . ?
N12 C11 C10 117.99(12) . . ?
C3 C4 C5 116.97(12) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C9 C10 C11 117.80(12) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C10 C9 N8 122.10(12) . . ?
C10 C9 H9 119.0 . . ?
N8 C9 H9 119.0 . . ?
C4 C3 N2 120.72(12) . . ?
C4 C3 H3 119.6 . . ?
N2 C3 H3 119.6 . . ?
C15 C16 C17 120.18(13) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C19 C14 C15 122.78(13) . . ?
C19 C14 N20 118.34(13) . . ?
C15 C14 N20 118.88(13) . . ?
O24 C23 O25 125.37(13) . . ?
O24 C23 C17 117.09(12) . . ?
O25 C23 C17 117.51(12) . . ?
C14 C19 C18 117.60(13) . . ?
C14 C19 H19 121.2 . . ?
C18 C19 H19 121.2 . . ?
C18 C17 C16 119.42(13) . . ?
C18 C17 C23 118.71(12) . . ?
C16 C17 C23 121.85(12) . . ?
C19 C18 C17 121.35(13) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C14 C15 C16 118.64(13) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?

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
C1 N6 C5 N5 -177.79(11) . . . . ?
C1 N6 C5 C4 2.28(18) . . . . ?
C9 N8 C7 O7 -179.38(11) . . . . ?
C9 N8 C7 N12 0.52(17) . . . . ?
C11 N12 C7 O7 179.95(11) . . . . ?
C11 N12 C7 N8 0.05(17) . . . . ?
C5 N6 C1 O1 178.77(11) . . . . ?
C5 N6 C1 N2 -0.71(17) . . . . ?
C3 N2 C1 O1 179.50(11) . . . . ?
C3 N2 C1 N6 -1.00(18) . . . . ?
C7 N12 C11 N11 178.72(11) . . . . ?
C7 N12 C11 C10 -0.90(18) . . . . ?
N5 C5 C4 C3 177.96(12) . . . . ?
N6 C5 C4 C3 -2.11(18) . . . . ?
N11 C11 C10 C9 -178.42(12) . . . . ?
N12 C11 C10 C9 1.18(17) . . . . ?
C11 C10 C9 N8 -0.67(18) . . . . ?
C7 N8 C9 C10 -0.20(19) . . . . ?
C5 C4 C3 N2 0.37(18) . . . . ?
C1 N2 C3 C4 1.14(19) . . . . ?
O22 N20 C14 C19 -3.5(2) . . . . ?
O21 N20 C14 C19 176.75(13) . . . . ?
O22 N20 C14 C15 176.36(13) . . . . ?
O21 N20 C14 C15 -3.4(2) . . . . ?
C15 C14 C19 C18 0.5(2) . . . . ?
N20 C14 C19 C18 -179.62(12) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C15 C16 C17 C23 -177.26(13) . . . . ?
O24 C23 C17 C18 1.4(2) . . . . ?
O25 C23 C17 C18 -177.00(12) . . . . ?
O24 C23 C17 C16 179.86(13) . . . . ?
O25 C23 C17 C16 1.5(2) . . . . ?
C14 C19 C18 C17 0.9(2) . . . . ?
C16 C17 C18 C19 -1.8(2) . . . . ?
C23 C17 C18 C19 176.71(13) . . . . ?
C19 C14 C15 C16 -1.1(2) . . . . ?
N20 C14 C15 C16 179.06(12) . . . . ?
C17 C16 C15 C14 0.2(2) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_exp_2045_auto
_database_code_depnum_ccdc_archive 'CCDC 2533644'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda - Raj Olga Ksiazkiewicz'
;Department of Physical Chemistry, Faculty of Chemistry, University of Lodz
Poland
;
_audit_update_record             
;
2026-02-26 deposited with the CCDC.	2026-06-09 downloaded from the CCDC.
;
_audit_creation_date             2025-01-07
_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         'C7 H3 N2 O7, C4 H6 N3 O, C4 H5 N3 O'
_chemical_formula_sum            'C15 H14 N8 O9'
_chemical_formula_weight         450.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H12 N8 O9'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3555(2)
_cell_length_b                   9.9675(2)
_cell_length_c                   10.8443(2)
_cell_angle_alpha                93.2367(17)
_cell_angle_beta                 95.2184(19)
_cell_angle_gamma                99.8519(19)
_cell_volume                     883.75(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14642
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3630
_cell_measurement_theta_min      4.0810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.627
_diffrn_reflns_theta_min         4.105
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -22.00   0.50    0.09    --  -91.75 125.00 120.00  126
  2  ω   -119.00 -33.00   0.50    0.05    --  -47.11 -51.00-148.28  172
  3  ω   -119.00 -92.00   0.50    0.05    --  -47.11 -57.00-120.00   54
  4  ω   -119.00 -34.00   0.50    0.05    --  -47.11 -49.00-115.62  170
  5  ω   -119.00 -34.00   0.50    0.05    --  -47.11 -50.00 -47.88  170
  6  ω   -119.00 -92.00   0.50    0.05    --  -47.11 -57.00 -60.00   54
  7  ω   -119.00 -92.00   0.50    0.05    --  -47.11 -57.00 -30.00   54
  8  ω   -119.00 -34.00   0.50    0.05    --  -47.11 -45.00 -69.88  170
  9  ω   -119.00 -33.00   0.50    0.05    --  -47.11 -48.00   8.85  172
 10  ω   -119.00 -34.00   0.50    0.05    --  -47.11 -43.00  44.00  170
 11  ω   -119.00 -34.00   0.50    0.05    --  -47.11 -50.00 120.17  170
 12  ω   -120.00 -34.00   0.50    0.05    --  -47.11 -38.00 150.00  172
 13  ω    -39.00  26.00   0.50    0.05    --  -47.11  38.00 120.00  130
 14  ω    -49.00 -20.00   0.50    0.09    --  -91.75  45.00 150.00   58
 15  ω    -49.00 -20.00   0.50    0.09    --  -91.75  45.00  30.00   58
 16  ω    -70.00  22.00   0.50    0.05    --  -47.11  77.00   0.00  184
 17  ω    -49.00 -20.00   0.50    0.09    --  -91.75  45.00 -90.00   58
 18  ω    -49.00 -20.00   0.50    0.09    --  -91.75  45.00-150.00   58
 19  ω   -163.00 -79.00   0.50    0.09    --  -91.75 -45.00-114.85  168
 20  ω   -163.00-104.00   0.50    0.09    --  -91.75 -77.00-120.00  118
 21  ω   -163.00-104.00   0.50    0.09    --  -91.75 -77.00 -30.00  118
 22  ω   -163.00 -97.00   0.50    0.09    --  -91.75 -61.00   0.00  132
 23  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -52.00   6.82  170
 24  ω   -163.00-104.00   0.50    0.09    --  -91.75 -77.00  90.00  118
 25  ω   -163.00-104.00   0.50    0.09    --  -91.75 -77.00 120.00  118
 26  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -52.00 104.03  170
 27  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -52.00  79.09  170
 28  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -51.00 -84.08  170
 29  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -52.00-120.77  170
 30  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -51.00 -67.08  170
 31  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -50.00 -40.59  170
 32  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -50.00  33.06  170
 33  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -51.00 172.15  170
 34  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -49.00 131.72  170
 35  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -50.00  50.35  170
 36  ω   -163.00 -78.00   0.50    0.09    --  -91.75 -48.00-156.85  170
 37  ω   -163.00-103.00   0.50    0.09    --  -91.75 -95.00-180.00  120
 38  ω   -163.00-103.00   0.50    0.09    --  -91.75 -95.00 -30.00  120
 39  ω     33.00  75.00   0.50    0.09    --  105.58 -61.00  30.00   84
 40  ω     33.00  75.00   0.50    0.09    --  105.58 -61.00   0.00   84
 41  ω     33.00  75.00   0.50    0.09    --  105.58 -61.00 -60.00   84
 42  ω     33.00  75.00   0.50    0.09    --  105.58 -61.00 -90.00   84
 43  ω     33.00  75.00   0.50    0.09    --  105.58 -61.00-120.00   84
 44  ω     34.00  93.00   0.50    0.05    --   47.11-125.00-180.00  118
 45  ω     36.00 111.00   0.50    0.09    --  105.58-125.00-120.00  150
 46  ω     35.00 106.00   0.50    0.09    --  105.58 -99.00-139.36  142
 47  ω     33.00 105.00   0.50    0.09    --  105.58 -95.00 -90.00  144
 48  ω     33.00 105.00   0.50    0.09    --  105.58 -95.00 -60.00  144
 49  ω     33.00 105.00   0.50    0.09    --  105.58 -95.00 -30.00  144
 50  ω     36.00 111.00   0.50    0.09    --  105.58-125.00  90.00  150
 51  ω     33.00 105.00   0.50    0.09    --  105.58 -95.00 120.00  144
 52  ω     33.00 105.00   0.50    0.09    --  105.58 -95.00  90.00  144
 53  ω     34.00 120.00   0.50    0.05    --   47.11  51.00 149.65  172
 54  ω     97.00 178.00   0.50    0.09    --  105.58  61.00   0.00  162
 55  ω     92.00 120.00   0.50    0.05    --   47.11  57.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0600022000
_diffrn_orient_matrix_UB_12      0.1306647000
_diffrn_orient_matrix_UB_13      -0.0389797000
_diffrn_orient_matrix_UB_21      0.1572865000
_diffrn_orient_matrix_UB_22      0.0872434000
_diffrn_orient_matrix_UB_23      0.0668520000
_diffrn_orient_matrix_UB_31      0.0839707000
_diffrn_orient_matrix_UB_32      -0.0075850000
_diffrn_orient_matrix_UB_33      -0.1202977000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3263
_reflns_number_total             3517
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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  (Sheldrick, 2015)'
_refine_diff_density_max         1.393
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0973P)²+0.4674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1441
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C10(H10), C9(H9), C4(H4), C3(H3)
2.b X=CH2 refined with riding coordinates:
 N11(H11a,H11b), N5(H5a,H5b)
;
_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
O7 O -0.29727(14) 0.04371(13) 0.97788(11) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.17192(14) 0.09479(12) 0.67967(11) 0.0232(3) Uani 1 1 d . . . . .
O28 O 0.73101(16) 0.35896(14) 0.84443(12) 0.0279(3) Uani 1 1 d . . . . .
O21 O 1.20686(15) 0.33935(13) 0.33796(12) 0.0273(3) Uani 1 1 d . . . . .
O29 O 0.61283(14) 0.25643(12) 0.66497(11) 0.0248(3) Uani 1 1 d . . . . .
O22 O 0.95338(15) 0.23770(13) 0.31805(11) 0.0263(3) Uani 1 1 d . . . . .
O25 O 1.29545(17) 0.63980(14) 0.85095(13) 0.0353(3) Uani 1 1 d . . . . .
N8 N -0.49948(17) -0.05618(14) 0.83210(13) 0.0200(3) Uani 1 1 d . . . . .
N12 N -0.23076(17) 0.00905(14) 0.78101(13) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.35622(17) 0.22708(14) 0.82388(13) 0.0198(3) Uani 1 1 d . . . . .
N6 N 0.08971(17) 0.15241(14) 0.86595(12) 0.0185(3) Uani 1 1 d . . . . .
O26 O 1.01114(17) 0.47952(14) 0.86606(13) 0.0347(3) Uani 1 1 d . . . . .
N11 N -0.17287(18) -0.02489(15) 0.58100(13) 0.0218(3) Uani 1 1 d . . . . .
H11A H -0.071085 0.013576 0.604861 0.026 Uiso 1 1 calc R U . . .
H11B H -0.202080 -0.054559 0.502865 0.026 Uiso 1 1 calc R U . . .
O24 O 1.45485(16) 0.53920(15) 0.74585(15) 0.0394(4) Uani 1 1 d . . . . .
N20 N 1.07412(17) 0.30465(14) 0.38108(13) 0.0217(3) Uani 1 1 d . . . . .
N5 N -0.00212(19) 0.20736(16) 1.05124(14) 0.0272(3) Uani 1 1 d . . . . .
H5A H -0.098226 0.159374 1.023051 0.033 Uiso 1 1 calc R U . . .
H5B H 0.012882 0.248462 1.126423 0.033 Uiso 1 1 calc R U . . .
N23 N 1.31891(19) 0.55558(15) 0.77064(14) 0.0260(3) Uani 1 1 d . . . . .
C18 C 0.8939(2) 0.35752(16) 0.67728(15) 0.0195(3) Uani 1 1 d . . . . .
C27 C 0.7336(2) 0.32086(17) 0.72918(15) 0.0210(4) Uani 1 1 d . . . . .
C14 C 1.0607(2) 0.34663(16) 0.50905(15) 0.0200(4) Uani 1 1 d . . . . .
C7 C -0.3394(2) 0.00075(16) 0.86679(15) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.2056(2) 0.15458(16) 0.78314(15) 0.0190(3) Uani 1 1 d . . . . .
C15 C 1.1956(2) 0.42378(16) 0.57928(16) 0.0208(4) Uani 1 1 d . . . . .
H15 H 1.297799 0.443857 0.546351 0.025 Uiso 1 1 calc R U . . .
C16 C 1.1768(2) 0.47088(17) 0.69925(16) 0.0215(4) Uani 1 1 d . . . . .
C17 C 1.0273(2) 0.44009(16) 0.75464(15) 0.0206(4) Uani 1 1 d . . . . .
C19 C 0.9104(2) 0.31344(16) 0.55711(15) 0.0191(3) Uani 1 1 d . . . . .
H19 H 0.819726 0.260598 0.507000 0.023 Uiso 1 1 calc R U . . .
C10 C -0.4484(2) -0.10015(17) 0.62556(15) 0.0209(4) Uani 1 1 d . . . . .
H10 H -0.483304 -0.135239 0.542398 0.025 Uiso 1 1 calc R U . . .
C9 C -0.5527(2) -0.10650(17) 0.71358(15) 0.0207(4) Uani 1 1 d . . . . .
H9 H -0.664238 -0.146406 0.692690 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1176(2) 0.21751(17) 0.98186(15) 0.0212(4) Uani 1 1 d . . . . .
C4 C 0.2771(2) 0.29217(18) 1.02003(16) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.302388 0.339642 1.099761 0.028 Uiso 1 1 calc R U . . .
C11 C -0.2827(2) -0.03820(16) 0.66315(15) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.3910(2) 0.29348(17) 0.93968(16) 0.0221(4) Uani 1 1 d . . . . .
H3 H 0.498491 0.341799 0.964036 0.026 Uiso 1 1 calc R U . . .
H6 H -0.009(3) 0.101(2) 0.837(2) 0.023(5) Uiso 1 1 d . . . . .
H8 H -0.568(3) -0.061(2) 0.894(2) 0.031(6) Uiso 1 1 d . . . . .
H2 H 0.426(3) 0.231(3) 0.771(2) 0.038(6) Uiso 1 1 d . . . . .
H28 H 0.837(6) 0.405(4) 0.879(4) 0.108(14) 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
O7 C7 1.254(2) . ?
O1 C1 1.226(2) . ?
O28 C27 1.289(2) . ?
O28 H28 0.96(5) . ?
O21 N20 1.2449(18) . ?
O29 C27 1.231(2) . ?
O22 N20 1.2341(19) . ?
O25 N23 1.227(2) . ?
N8 C7 1.370(2) . ?
N8 C9 1.360(2) . ?
N8 H8 0.92(3) . ?
N12 C7 1.354(2) . ?
N12 C11 1.344(2) . ?
N2 C1 1.361(2) . ?
N2 C3 1.369(2) . ?
N2 H2 0.86(3) . ?
N6 C1 1.378(2) . ?
N6 C5 1.363(2) . ?
N6 H6 0.91(2) . ?
O26 C17 1.276(2) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C11 1.332(2) . ?
O24 N23 1.226(2) . ?
N20 C14 1.446(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C5 1.299(2) . ?
N23 C16 1.462(2) . ?
C18 C27 1.496(2) . ?
C18 C17 1.436(2) . ?
C18 C19 1.378(2) . ?
C14 C15 1.386(2) . ?
C14 C19 1.398(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 C17 1.428(2) . ?
C19 H19 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.347(2) . ?
C10 C11 1.428(2) . ?
C9 H9 0.9500 . ?
C5 C4 1.423(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.347(2) . ?
C3 H3 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
C27 O28 H28 110(3) . . ?
C7 N8 H8 116.4(15) . . ?
C9 N8 C7 121.81(14) . . ?
C9 N8 H8 121.8(15) . . ?
C11 N12 C7 119.12(14) . . ?
C1 N2 C3 122.37(14) . . ?
C1 N2 H2 115.0(17) . . ?
C3 N2 H2 122.6(17) . . ?
C1 N6 H6 113.7(14) . . ?
C5 N6 C1 124.27(14) . . ?
C5 N6 H6 122.0(14) . . ?
H11A N11 H11B 120.0 . . ?
C11 N11 H11A 120.0 . . ?
C11 N11 H11B 120.0 . . ?
O21 N20 C14 118.61(14) . . ?
O22 N20 O21 122.34(14) . . ?
O22 N20 C14 119.04(14) . . ?
H5A N5 H5B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
O25 N23 C16 118.24(15) . . ?
O24 N23 O25 123.77(15) . . ?
O24 N23 C16 117.98(15) . . ?
C17 C18 C27 118.57(15) . . ?
C19 C18 C27 119.92(15) . . ?
C19 C18 C17 121.50(15) . . ?
O28 C27 C18 116.03(15) . . ?
O29 C27 O28 122.66(15) . . ?
O29 C27 C18 121.30(15) . . ?
C15 C14 N20 119.04(15) . . ?
C15 C14 C19 121.70(15) . . ?
C19 C14 N20 119.20(15) . . ?
O7 C7 N8 118.86(14) . . ?
O7 C7 N12 121.60(14) . . ?
N12 C7 N8 119.54(14) . . ?
O1 C1 N2 123.35(15) . . ?
O1 C1 N6 120.95(15) . . ?
N2 C1 N6 115.70(14) . . ?
C14 C15 H15 121.0 . . ?
C14 C15 C16 118.05(15) . . ?
C16 C15 H15 121.0 . . ?
C15 C16 N23 117.31(15) . . ?
C15 C16 C17 123.25(15) . . ?
C17 C16 N23 119.44(15) . . ?
O26 C17 C18 121.00(16) . . ?
O26 C17 C16 123.40(16) . . ?
C16 C17 C18 115.58(15) . . ?
C18 C19 C14 119.89(15) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C9 C10 H10 121.6 . . ?
C9 C10 C11 116.87(15) . . ?
C11 C10 H10 121.6 . . ?
N8 C9 H9 119.8 . . ?
C10 C9 N8 120.44(15) . . ?
C10 C9 H9 119.8 . . ?
N6 C5 C4 117.88(15) . . ?
N5 C5 N6 118.31(15) . . ?
N5 C5 C4 123.82(16) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 C5 117.98(16) . . ?
C3 C4 H4 121.0 . . ?
N12 C11 C10 122.20(15) . . ?
N11 C11 N12 117.24(15) . . ?
N11 C11 C10 120.55(15) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 N2 121.80(16) . . ?
C4 C3 H3 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O21 N20 C14 C15 0.0(2) . . . . ?
O21 N20 C14 C19 177.25(14) . . . . ?
O22 N20 C14 C15 -178.94(14) . . . . ?
O22 N20 C14 C19 -1.7(2) . . . . ?
O25 N23 C16 C15 151.82(16) . . . . ?
O25 N23 C16 C17 -28.4(2) . . . . ?
N6 C5 C4 C3 -0.3(2) . . . . ?
O24 N23 C16 C15 -27.5(2) . . . . ?
O24 N23 C16 C17 152.32(17) . . . . ?
N20 C14 C15 C16 175.67(14) . . . . ?
N20 C14 C19 C18 -177.34(14) . . . . ?
N5 C5 C4 C3 179.29(17) . . . . ?
N23 C16 C17 O26 -2.1(3) . . . . ?
N23 C16 C17 C18 179.38(14) . . . . ?
C27 C18 C17 O26 1.3(2) . . . . ?
C27 C18 C17 C16 179.86(14) . . . . ?
C27 C18 C19 C14 -179.38(14) . . . . ?
C14 C15 C16 N23 -178.17(14) . . . . ?
C14 C15 C16 C17 2.1(2) . . . . ?
C7 N8 C9 C10 -0.8(2) . . . . ?
C7 N12 C11 N11 178.29(14) . . . . ?
C7 N12 C11 C10 -1.6(2) . . . . ?
C1 N2 C3 C4 -0.8(3) . . . . ?
C1 N6 C5 N5 -179.90(15) . . . . ?
C1 N6 C5 C4 -0.2(2) . . . . ?
C15 C14 C19 C18 -0.1(2) . . . . ?
C15 C16 C17 O26 177.68(15) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C17 C18 C27 O28 -4.8(2) . . . . ?
C17 C18 C27 O29 176.16(15) . . . . ?
C17 C18 C19 C14 1.4(2) . . . . ?
C19 C18 C27 O28 175.95(15) . . . . ?
C19 C18 C27 O29 -3.1(2) . . . . ?
C19 C18 C17 O26 -179.48(15) . . . . ?
C19 C18 C17 C16 -0.9(2) . . . . ?
C19 C14 C15 C16 -1.5(2) . . . . ?
C9 N8 C7 O7 -179.03(15) . . . . ?
C9 N8 C7 N12 0.8(2) . . . . ?
C9 C10 C11 N12 1.5(2) . . . . ?
C9 C10 C11 N11 -178.30(15) . . . . ?
C5 N6 C1 O1 -179.28(15) . . . . ?
C5 N6 C1 N2 0.3(2) . . . . ?
C5 C4 C3 N2 0.8(3) . . . . ?
C11 N12 C7 O7 -179.79(15) . . . . ?
C11 N12 C7 N8 0.4(2) . . . . ?
C11 C10 C9 N8 -0.3(2) . . . . ?
C3 N2 C1 O1 179.76(16) . . . . ?
C3 N2 C1 N6 0.2(2) . . . . ?

_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 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.718
####################################################################### 
# 
# 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_exp_2048_auto
_database_code_depnum_ccdc_archive 'CCDC 2533643'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda-Raj Olga Ksiazkiewicz'
;Department of Physical Chemistry, Faculty of Chemistry, University of Lodz
Poland
;
_audit_update_record             
;
2026-02-26 deposited with the CCDC.	2026-06-09 downloaded from the CCDC.
;
_audit_creation_date             2025-01-07
_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         'C7 H3 N2 O6, C4 H6 N3 O, 3(H2 O)'
_chemical_formula_sum            'C11 H15 N5 O10'
_chemical_formula_weight         377.28
_chemical_melting_point          ?
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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.93124(3)
_cell_length_b                   24.69141(15)
_cell_length_c                   12.91178(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.8731(5)
_cell_angle_gamma                90
_cell_volume                     1571.289(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25017
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.8070
_cell_measurement_theta_min      3.4430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.081
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.581
_diffrn_reflns_theta_min         3.580
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  12.00   0.50    0.05    --   47.36 -19.00-180.00   78
  2  ω    -25.00  39.00   0.50    0.05    --   47.36 -38.00-180.00  128
  3  ω    -27.00  12.00   0.50    0.05    --   47.36 -19.00 120.00   78
  4  ω     95.00 175.00   0.50    0.10    --  105.58 125.00  60.00  160
  5  ω     35.00 120.00   0.50    0.05    --   47.36  38.00 -60.00  170
  6  ω     34.00 120.00   0.50    0.05    --   47.36  50.00 -24.45  172
  7  ω     92.00 120.00   0.50    0.05    --   47.36  57.00-120.00   56
  8  ω     34.00 120.00   0.50    0.05    --   47.36  49.00 -45.62  172
  9  ω     34.00 104.00   0.50    0.05    --   47.36  51.00  14.89  140
 10  ω     34.00 120.00   0.50    0.05    --   47.36  50.00 155.01  172
 11  ω     34.00 120.00   0.50    0.05    --   47.36  50.00 105.09  172
 12  ω     35.00 120.00   0.50    0.05    --   47.36  47.00  53.68  170
 13  ω     35.00 120.00   0.50    0.05    --   47.36  38.00-120.00  170
 14  ω     33.00  75.00   0.50    0.10    --  105.58 -61.00 -30.00   84
 15  ω     33.00  75.00   0.50    0.10    --  105.58 -61.00   0.00   84
 16  ω     33.00  75.00   0.50    0.10    --  105.58 -61.00-120.00   84
 17  ω     33.00  75.00   0.50    0.10    --  105.58 -61.00-150.00   84
 18  ω     33.00 105.00   0.50    0.10    --  105.58 -95.00-120.00  144
 19  ω     34.00  93.00   0.50    0.05    --   47.36-125.00  30.00  118
 20  ω     36.00 111.00   0.50    0.10    --  105.58-125.00  90.00  150
 21  ω    -86.00 -13.00   0.50    0.05    --  -47.36 125.00   0.00  146
 22  ω    -85.00 -22.00   0.50    0.10    --  -91.75 125.00  30.00  126
 23  ω    -85.00 -22.00   0.50    0.10    --  -91.75 125.00  90.00  126
 24  ω    -12.00  28.00   0.50    0.05    --  -47.36  19.00 120.00   80
 25  ω    -49.00 -20.00   0.50    0.10    --  -91.75  45.00 120.00   58
 26  ω    -75.00 -19.00   0.50    0.10    --  -91.75  61.00-150.00  112
 27  ω    -49.00 -20.00   0.50    0.10    --  -91.75  45.00-150.00   58
 28  ω   -163.00 -79.00   0.50    0.10    --  -91.75 -45.00-150.00  168
 29  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -52.00 -85.92  170
 30  ω   -163.00 -86.00   0.50    0.10    --  -91.75 -54.00 -61.48  154
 31  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -52.00-144.55  170
 32  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -52.00 -79.68  170
 33  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -51.00-102.88  170
 34  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -52.00-132.71  170
 35  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -51.00-155.70  170
 36  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -51.00-157.90  170
 37  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -50.00-122.28  170
 38  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -50.00-116.30  170
 39  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -48.00-103.18  170
 40  ω   -163.00 -88.00   0.50    0.10    --  -91.75 -55.00 -43.12  150
 41  ω   -163.00 -79.00   0.50    0.10    --  -91.75 -45.00-102.42  168
 42  ω   -119.00 -92.00   0.50    0.05    --  -47.36 -57.00  30.00   54
 43  ω   -163.00 -97.00   0.50    0.10    --  -91.75 -61.00 120.00  132
 44  ω   -163.00 -78.00   0.50    0.10    --  -91.75 -49.00 178.04  170
 45  ω   -163.00-103.00   0.50    0.10    --  -91.75 -95.00  90.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2778882000
_diffrn_orient_matrix_UB_12      -0.0080854000
_diffrn_orient_matrix_UB_13      0.0489743000
_diffrn_orient_matrix_UB_21      0.1381803000
_diffrn_orient_matrix_UB_22      -0.0308820000
_diffrn_orient_matrix_UB_23      0.0909807000
_diffrn_orient_matrix_UB_31      0.0376637000
_diffrn_orient_matrix_UB_32      0.0535971000
_diffrn_orient_matrix_UB_33      0.0597885000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2974
_reflns_number_total             3104
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0023(3)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.6038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O9-H9a = O9-H9b
 0.87 with sigma of 0.02
 O7-H7a = O7-H7b
 0.87 with sigma of 0.02
 O8-H8a = O8-H8b
 0.87 with sigma of 0.02
 H7a-H7b
 1.38 with sigma of 0.04
 H9a-H9b
 1.38 with sigma of 0.04
 H8a-H8b
 1.38 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C19(H19), C3(H3), C4(H4)
3.b X=CH2 refined with riding coordinates:
 N5(H5a,H5b)
;
_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
O29 O 0.39189(16) 0.30211(3) 0.64956(6) 0.01715(19) Uani 1 1 d . . . . .
O28 O 0.31019(16) 0.35525(3) 0.78490(6) 0.01748(19) Uani 1 1 d . . . . .
O1 O 0.11276(17) 0.17148(3) 0.54828(6) 0.0202(2) Uani 1 1 d . . . . .
O21 O 1.33428(17) 0.42515(4) 0.43535(7) 0.0235(2) Uani 1 1 d . . . . .
O22 O 1.12441(18) 0.34815(4) 0.42074(7) 0.0234(2) Uani 1 1 d . . . . .
N6 N -0.00029(19) 0.22437(4) 0.68599(7) 0.0137(2) Uani 1 1 d . . . . .
O25 O 0.78574(18) 0.53110(3) 0.80721(7) 0.0224(2) Uani 1 1 d . . . . .
N2 N -0.22938(19) 0.14430(4) 0.64918(7) 0.0147(2) Uani 1 1 d . . . . .
N23 N 0.9443(2) 0.51740(4) 0.74112(7) 0.0177(2) Uani 1 1 d . . . . .
O24 O 1.14273(19) 0.54390(4) 0.71612(7) 0.0289(2) Uani 1 1 d . . . . .
C17 C 0.6970(2) 0.43117(4) 0.72127(8) 0.0141(2) Uani 1 1 d . . . . .
H17 H 0.593290 0.440598 0.779317 0.017 Uiso 1 1 calc R U . . .
C15 C 1.0530(2) 0.45431(4) 0.60265(8) 0.0149(2) Uani 1 1 d . . . . .
H15 H 1.189197 0.478517 0.580530 0.018 Uiso 1 1 calc R U . . .
C19 C 0.8057(2) 0.36935(4) 0.58415(8) 0.0141(2) Uani 1 1 d . . . . .
H19 H 0.776757 0.336218 0.548043 0.017 Uiso 1 1 calc R U . . .
C16 C 0.8954(2) 0.46577(4) 0.68652(8) 0.0145(2) Uani 1 1 d . . . . .
C1 C -0.0309(2) 0.17951(4) 0.62210(8) 0.0147(2) Uani 1 1 d . . . . .
C3 C -0.3928(2) 0.15298(4) 0.73009(9) 0.0147(2) Uani 1 1 d . . . . .
H3 H -0.530929 0.127396 0.743860 0.018 Uiso 1 1 calc R U . . .
C5 C -0.1515(2) 0.23399(4) 0.77047(8) 0.0132(2) Uani 1 1 d . . . . .
C18 C 0.6521(2) 0.38217(4) 0.66947(8) 0.0132(2) Uani 1 1 d . . . . .
O9 O 0.54553(18) 0.23371(4) 0.49278(7) 0.0202(2) Uani 1 1 d D . . . .
H9A H 0.415(3) 0.2113(6) 0.5023(13) 0.030 Uiso 1 1 d D U . . .
H9B H 0.514(3) 0.2591(6) 0.5368(12) 0.030 Uiso 1 1 d D U . . .
O7 O -0.28315(17) 0.05337(3) 0.52480(6) 0.01754(19) Uani 1 1 d D . . . .
H7A H -0.440(3) 0.0553(7) 0.4936(12) 0.026 Uiso 1 1 d D U . . .
H7B H -0.274(3) 0.0219(6) 0.5538(12) 0.026 Uiso 1 1 d D U . . .
O8 O -0.78151(17) 0.05821(3) 0.41575(6) 0.01807(19) Uani 1 1 d D . . . .
H8A H -0.922(3) 0.0648(7) 0.4521(12) 0.027 Uiso 1 1 d D U . . .
H8B H -0.761(3) 0.0876(6) 0.3776(12) 0.027 Uiso 1 1 d D U . . .
N5 N -0.09545(19) 0.27600(4) 0.82920(7) 0.0152(2) Uani 1 1 d . . . . .
H5A H 0.038922 0.297736 0.813957 0.018 Uiso 1 1 calc R U . . .
H5B H -0.192140 0.282504 0.883926 0.018 Uiso 1 1 calc R U . . .
N20 N 1.16482(19) 0.39183(4) 0.46289(7) 0.0167(2) Uani 1 1 d . . . . .
C27 C 0.4338(2) 0.34336(4) 0.70513(8) 0.0135(2) Uani 1 1 d . . . . .
C14 C 1.0012(2) 0.40558(5) 0.55270(8) 0.0142(2) Uani 1 1 d . . . . .
C4 C -0.3646(2) 0.19687(4) 0.79137(8) 0.0147(2) Uani 1 1 d . . . . .
H4 H -0.482840 0.202930 0.846824 0.018 Uiso 1 1 calc R U . . .
H6 H 0.127(3) 0.2495(7) 0.6730(12) 0.022(4) Uiso 1 1 d . . . . .
H2 H -0.249(3) 0.1158(7) 0.6114(13) 0.025(4) 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
O29 C27 1.2592(13) . ?
O28 C27 1.2487(14) . ?
O1 C1 1.2222(14) . ?
O21 N20 1.2334(13) . ?
O22 N20 1.2215(13) . ?
N6 C1 1.3864(14) . ?
N6 C5 1.3622(14) . ?
N6 H6 0.903(17) . ?
O25 N23 1.2236(13) . ?
N2 C1 1.3632(15) . ?
N2 C3 1.3572(15) . ?
N2 H2 0.861(18) . ?
N23 O24 1.2292(14) . ?
N23 C16 1.4729(14) . ?
C17 H17 0.9500 . ?
C17 C16 1.3844(16) . ?
C17 C18 1.3967(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.3826(16) . ?
C15 C14 1.3849(16) . ?
C19 H19 0.9500 . ?
C19 C18 1.3936(15) . ?
C19 C14 1.3860(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3463(16) . ?
C5 N5 1.3092(14) . ?
C5 C4 1.4265(15) . ?
C18 C27 1.5236(15) . ?
O9 H9A 0.859(14) . ?
O9 H9B 0.863(14) . ?
O7 H7A 0.861(13) . ?
O7 H7B 0.863(13) . ?
O8 H8A 0.865(13) . ?
O8 H8B 0.885(13) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N20 C14 1.4737(14) . ?
C4 H4 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
C1 N6 H6 120.0(10) . . ?
C5 N6 C1 124.32(10) . . ?
C5 N6 H6 115.6(10) . . ?
C1 N2 H2 116.5(10) . . ?
C3 N2 C1 123.10(10) . . ?
C3 N2 H2 120.4(10) . . ?
O25 N23 O24 124.64(10) . . ?
O25 N23 C16 118.34(9) . . ?
O24 N23 C16 117.02(10) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.82(10) . . ?
C18 C17 H17 120.6 . . ?
C16 C15 H15 121.9 . . ?
C16 C15 C14 116.28(10) . . ?
C14 C15 H15 121.9 . . ?
C18 C19 H19 120.4 . . ?
C14 C19 H19 120.4 . . ?
C14 C19 C18 119.10(10) . . ?
C17 C16 N23 119.03(10) . . ?
C15 C16 N23 117.68(10) . . ?
C15 C16 C17 123.29(10) . . ?
O1 C1 N6 122.61(10) . . ?
O1 C1 N2 122.40(10) . . ?
N2 C1 N6 114.97(10) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 N2 121.80(10) . . ?
C4 C3 H3 119.1 . . ?
N6 C5 C4 117.73(10) . . ?
N5 C5 N6 119.42(10) . . ?
N5 C5 C4 122.85(10) . . ?
C17 C18 C27 120.18(10) . . ?
C19 C18 C17 119.57(10) . . ?
C19 C18 C27 120.25(10) . . ?
H9A O9 H9B 102.9(15) . . ?
H7A O7 H7B 106.6(15) . . ?
H8A O8 H8B 104.8(14) . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O21 N20 C14 117.81(9) . . ?
O22 N20 O21 124.25(10) . . ?
O22 N20 C14 117.94(9) . . ?
O29 C27 C18 116.15(10) . . ?
O28 C27 O29 125.79(10) . . ?
O28 C27 C18 118.04(9) . . ?
C15 C14 C19 122.94(10) . . ?
C15 C14 N20 118.00(10) . . ?
C19 C14 N20 119.06(10) . . ?
C3 C4 C5 117.95(10) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O21 N20 C14 C15 -1.88(15) . . . . ?
O21 N20 C14 C19 178.78(10) . . . . ?
O22 N20 C14 C15 177.92(10) . . . . ?
O22 N20 C14 C19 -1.41(15) . . . . ?
N6 C5 C4 C3 3.85(15) . . . . ?
O25 N23 C16 C17 -8.96(15) . . . . ?
O25 N23 C16 C15 171.33(10) . . . . ?
N2 C3 C4 C5 -1.45(16) . . . . ?
O24 N23 C16 C17 171.43(10) . . . . ?
O24 N23 C16 C15 -8.28(15) . . . . ?
C17 C18 C27 O29 174.70(10) . . . . ?
C17 C18 C27 O28 -4.28(15) . . . . ?
C19 C18 C27 O29 -4.45(15) . . . . ?
C19 C18 C27 O28 176.57(10) . . . . ?
C16 C17 C18 C19 -0.35(16) . . . . ?
C16 C17 C18 C27 -179.50(9) . . . . ?
C16 C15 C14 C19 -0.70(16) . . . . ?
C16 C15 C14 N20 179.99(9) . . . . ?
C1 N6 C5 N5 175.99(10) . . . . ?
C1 N6 C5 C4 -3.39(16) . . . . ?
C1 N2 C3 C4 -1.77(17) . . . . ?
C3 N2 C1 O1 -179.13(10) . . . . ?
C3 N2 C1 N6 2.32(15) . . . . ?
C5 N6 C1 O1 -178.20(10) . . . . ?
C5 N6 C1 N2 0.35(15) . . . . ?
C18 C17 C16 N23 -179.77(9) . . . . ?
C18 C17 C16 C15 -0.08(17) . . . . ?
C18 C19 C14 C15 0.30(17) . . . . ?
C18 C19 C14 N20 179.61(9) . . . . ?
N5 C5 C4 C3 -175.50(10) . . . . ?
C14 C15 C16 N23 -179.72(9) . . . . ?
C14 C15 C16 C17 0.58(17) . . . . ?
C14 C19 C18 C17 0.24(16) . . . . ?
C14 C19 C18 C27 179.40(10) . . . . ?

_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 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.418
####################################################################### 
# 
# 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_exp_2069_auto
_database_code_depnum_ccdc_archive 'CCDC 2533642'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda-Raj Olga Ksiazkiewicz'
;Department of Physical Chemistry, Faculty of Chemistry, University of Lodz
Poland
;
_audit_update_record             
;
2026-02-26 deposited with the CCDC.	2026-06-09 downloaded from the CCDC.
;
_audit_creation_date             2025-01-07
_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         'C7 H4 N O4, C4 H6 N3 O'
_chemical_formula_sum            'C11 H10 N4 O5'
_chemical_formula_weight         278.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   11.90240(10)
_cell_length_b                   15.66930(10)
_cell_length_c                   12.40120(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2312.85(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18526
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.4560
_cell_measurement_theta_min      3.5110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.917
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.167
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24293
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.592
_diffrn_reflns_theta_min         4.665
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00 -20.00   0.50    0.07    --  -91.75  45.00-150.00   58
  2  ω    -49.00 -20.00   0.50    0.07    --  -91.75  45.00 -90.00   58
  3  ω    -49.00 -20.00   0.50    0.07    --  -91.75  45.00 -30.00   58
  4  ω    -12.00  28.00   0.50    0.05    --  -47.24  19.00-150.00   80
  5  ω    -49.00 -20.00   0.50    0.07    --  -91.75  45.00  60.00   58
  6  ω    -49.00 -20.00   0.50    0.07    --  -91.75  45.00 150.00   58
  7  ω   -166.00 -78.00   0.50    0.07    --  -91.75 -15.00 -30.00  176
  8  ω   -163.00 -97.00   0.50    0.07    --  -91.75 -61.00 120.00  132
  9  ω   -163.00 -81.00   0.50    0.07    --  -91.75 -45.00 -90.00  164
 10  ω   -163.00-104.00   0.50    0.07    --  -91.75 -77.00-180.00  118
 11  ω   -161.00 -90.00   0.50    0.07    --  -91.75-125.00 -90.00  142
 12  ω   -119.00 -48.00   0.50    0.05    --  -47.24-164.00-138.00  142
 13  ω   -119.00 -92.00   0.50    0.05    --  -47.24 -57.00-180.00   54
 14  ω   -120.00 -35.00   0.50    0.05    --  -47.24 -38.00-150.00  170
 15  ω   -120.00 -35.00   0.50    0.05    --  -47.24 -38.00  30.00  170
 16  ω   -119.00 -92.00   0.50    0.05    --  -47.24 -57.00  60.00   54
 17  ω   -119.00 -92.00   0.50    0.05    --  -47.24 -57.00  90.00   54
 18  ω   -120.00 -35.00   0.50    0.05    --  -47.24 -38.00 120.00  170
 19  ω   -120.00 -35.00   0.50    0.05    --  -47.24 -38.00 -30.00  170
 20  ω   -120.00 -35.00   0.50    0.05    --  -47.24 -38.00 -90.00  170
 21  ω    -27.00  12.00   0.50    0.05    --   47.24 -19.00  30.00   78
 22  ω    -27.00  12.00   0.50    0.05    --   47.24 -19.00 -60.00   78
 23  ω     33.00  75.00   0.50    0.07    --  105.58 -61.00-180.00   84
 24  ω     33.00 128.00   0.50    0.07    --  105.58 -77.00-120.00  190
 25  ω     33.00  75.00   0.50    0.07    --  105.58 -61.00-120.00   84
 26  ω     33.00  75.00   0.50    0.07    --  105.58 -61.00 -60.00   84
 27  ω     33.00 105.00   0.50    0.07    --  105.58 -95.00  30.00  144
 28  ω     36.00 111.00   0.50    0.07    --  105.58-125.00  30.00  150
 29  ω     34.00  93.00   0.50    0.05    --   47.24-125.00-180.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0746618000
_diffrn_orient_matrix_UB_12      -0.0217085000
_diffrn_orient_matrix_UB_13      0.0977715000
_diffrn_orient_matrix_UB_21      -0.1039334000
_diffrn_orient_matrix_UB_22      -0.0023936000
_diffrn_orient_matrix_UB_23      -0.0739215000
_diffrn_orient_matrix_UB_31      0.0194680000
_diffrn_orient_matrix_UB_32      -0.0958552000
_diffrn_orient_matrix_UB_33      -0.0201975000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2275
_reflns_number_total             2359
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0029(3)
_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   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.101
_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)+(0.0574P)²+1.0110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1027
_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
2.a Aromatic/amide H refined with riding coordinates:
 N6(H6), N2(H2), C18(H18), C19(H19), C4(H4), C15(H15), C16(H16), C3(H3)
2.b X=CH2 refined with riding coordinates:
 N5(H5a,H5b)
;
_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
O1 O 0.87421(8) 0.44825(6) 0.50986(7) 0.0180(2) Uani 1 1 d . . . . .
O24 O 0.64967(8) 0.33592(6) 0.57439(7) 0.0211(2) Uani 1 1 d . . . . .
O25 O 0.58215(8) 0.30072(6) 0.73639(7) 0.0217(2) Uani 1 1 d . . . . .
O21 O 0.23207(8) 0.08885(6) 0.34354(7) 0.0233(2) Uani 1 1 d . . . . .
O22 O 0.15275(8) 0.07378(6) 0.49966(8) 0.0244(2) Uani 1 1 d . . . . .
N6 N 0.82476(9) 0.40427(6) 0.67743(8) 0.0150(2) Uani 1 1 d . . . . .
H6 H 0.766778 0.376677 0.650539 0.018 Uiso 1 1 calc R U . . .
N2 N 0.98243(9) 0.48975(6) 0.65233(9) 0.0165(2) Uani 1 1 d . . . . .
H2 H 1.027693 0.519026 0.610136 0.020 Uiso 1 1 calc R U . . .
N20 N 0.22813(9) 0.10099(6) 0.44180(9) 0.0176(3) Uani 1 1 d . . . . .
N5 N 0.76918(9) 0.35968(7) 0.84581(9) 0.0187(3) Uani 1 1 d . . . . .
H5A H 0.711408 0.333951 0.815736 0.022 Uiso 1 1 calc R U . . .
H5B H 0.778602 0.357292 0.916123 0.022 Uiso 1 1 calc R U . . .
C5 C 0.84105(10) 0.40146(8) 0.78598(10) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.31888(10) 0.15098(7) 0.49147(10) 0.0153(3) Uani 1 1 d . . . . .
C23 C 0.58064(10) 0.29828(7) 0.63556(10) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.89345(10) 0.44761(7) 0.60743(10) 0.0148(3) Uani 1 1 d . . . . .
C17 C 0.48802(10) 0.24622(7) 0.58335(10) 0.0149(3) Uani 1 1 d . . . . .
C18 C 0.40742(10) 0.20636(8) 0.64810(10) 0.0160(3) Uani 1 1 d . . . . .
H18 H 0.411620 0.212053 0.724264 0.019 Uiso 1 1 calc R U . . .
C19 C 0.32141(10) 0.15861(8) 0.60273(10) 0.0164(3) Uani 1 1 d . . . . .
H19 H 0.266056 0.132026 0.646523 0.020 Uiso 1 1 calc R U . . .
C4 C 0.93643(11) 0.44472(8) 0.82920(10) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.952264 0.443121 0.904254 0.021 Uiso 1 1 calc R U . . .
C15 C 0.39885(11) 0.18789(8) 0.42476(10) 0.0165(3) Uani 1 1 d . . . . .
H15 H 0.395880 0.180169 0.348833 0.020 Uiso 1 1 calc R U . . .
C16 C 0.48324(10) 0.23634(7) 0.47166(10) 0.0164(3) Uani 1 1 d . . . . .
H16 H 0.538159 0.262984 0.427420 0.020 Uiso 1 1 calc R U . . .
C3 C 1.00339(11) 0.48789(8) 0.76076(10) 0.0176(3) Uani 1 1 d . . . . .
H3 H 1.066630 0.517717 0.788408 0.021 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
O1 C1 1.2315(15) . ?
O24 C23 1.2643(16) . ?
O25 C23 1.2512(16) . ?
O21 N20 1.2342(14) . ?
O22 N20 1.2254(15) . ?
N6 H6 0.8800 . ?
N6 C5 1.3608(16) . ?
N6 C1 1.3722(16) . ?
N2 H2 0.8800 . ?
N2 C1 1.3667(16) . ?
N2 C3 1.3680(16) . ?
N20 C14 1.4695(15) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C5 1.3080(17) . ?
C5 C4 1.4267(18) . ?
C14 C19 1.3854(18) . ?
C14 C15 1.3874(18) . ?
C23 C17 1.5165(16) . ?
C17 C18 1.3984(17) . ?
C17 C16 1.3948(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.3872(18) . ?
C19 H19 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.3465(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3869(17) . ?
C16 H16 0.9500 . ?
C3 H3 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
C5 N6 H6 118.1 . . ?
C5 N6 C1 123.84(11) . . ?
C1 N6 H6 118.1 . . ?
C1 N2 H2 118.9 . . ?
C1 N2 C3 122.10(11) . . ?
C3 N2 H2 118.9 . . ?
O21 N20 C14 117.90(10) . . ?
O22 N20 O21 123.53(11) . . ?
O22 N20 C14 118.57(11) . . ?
H5A N5 H5B 120.0 . . ?
C5 N5 H5A 120.0 . . ?
C5 N5 H5B 120.0 . . ?
N6 C5 C4 118.01(11) . . ?
N5 C5 N6 118.95(11) . . ?
N5 C5 C4 123.03(12) . . ?
C19 C14 N20 118.65(11) . . ?
C19 C14 C15 122.88(11) . . ?
C15 C14 N20 118.46(11) . . ?
O24 C23 C17 117.85(11) . . ?
O25 C23 O24 125.18(12) . . ?
O25 C23 C17 116.98(11) . . ?
O1 C1 N6 120.99(11) . . ?
O1 C1 N2 122.71(11) . . ?
N2 C1 N6 116.30(11) . . ?
C18 C17 C23 119.59(11) . . ?
C16 C17 C23 120.88(11) . . ?
C16 C17 C18 119.52(11) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.95(11) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 117.82(11) . . ?
C14 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C5 C4 H4 120.9 . . ?
C3 C4 C5 118.22(12) . . ?
C3 C4 H4 120.9 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.36(12) . . ?
C16 C15 H15 120.8 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.44(11) . . ?
C15 C16 H16 119.8 . . ?
N2 C3 H3 119.3 . . ?
C4 C3 N2 121.49(12) . . ?
C4 C3 H3 119.3 . . ?

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
O24 C23 C17 C18 -177.51(11) . . . . ?
O24 C23 C17 C16 3.60(17) . . . . ?
O25 C23 C17 C18 2.19(16) . . . . ?
O25 C23 C17 C16 -176.70(11) . . . . ?
O21 N20 C14 C19 -174.15(11) . . . . ?
O21 N20 C14 C15 5.32(16) . . . . ?
O22 N20 C14 C19 5.97(16) . . . . ?
O22 N20 C14 C15 -174.55(11) . . . . ?
N6 C5 C4 C3 1.78(17) . . . . ?
N20 C14 C19 C18 -179.72(10) . . . . ?
N20 C14 C15 C16 178.83(10) . . . . ?
N5 C5 C4 C3 -178.13(12) . . . . ?
C5 N6 C1 O1 -179.63(11) . . . . ?
C5 N6 C1 N2 -0.11(17) . . . . ?
C5 C4 C3 N2 -0.90(18) . . . . ?
C14 C15 C16 C17 1.04(17) . . . . ?
C23 C17 C18 C19 179.73(11) . . . . ?
C23 C17 C16 C15 179.34(11) . . . . ?
C1 N6 C5 N5 178.61(11) . . . . ?
C1 N6 C5 C4 -1.30(17) . . . . ?
C1 N2 C3 C4 -0.55(18) . . . . ?
C17 C18 C19 C14 0.74(17) . . . . ?
C18 C17 C16 C15 0.45(17) . . . . ?
C19 C14 C15 C16 -1.71(18) . . . . ?
C15 C14 C19 C18 0.83(18) . . . . ?
C16 C17 C18 C19 -1.37(17) . . . . ?
C3 N2 C1 O1 -179.41(11) . . . . ?
C3 N2 C1 N6 1.07(16) . . . . ?

_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 1.758
_oxdiff_exptl_absorpt_empirical_full_min 0.384
