# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_NN-Et2H2oba
_database_code_depnum_ccdc_archive 'CCDC 2478688'
loop_
_audit_author_name
_audit_author_address
'Grazielli da Rocha'
;UFPR
Brazil
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     C22H22N4O6
_chemical_formula_moiety         'C22 H22 N4 O6'
_chemical_formula_sum            'C22 H22 N4 O6'
_chemical_formula_weight         438.43

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                   7.4167(2)
_cell_length_b                   11.8025(3)
_cell_length_c                   13.2319(4)
_cell_angle_alpha                114.5540(10)
_cell_angle_beta                 92.4900(10)
_cell_angle_gamma                96.2670(10)
_cell_volume                     1042.16(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      4.2343
_cell_measurement_theta_max      74.2867

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.865
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            28275
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.234
_diffrn_reflns_theta_max         73.999
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4192
_reflns_number_gt                3631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX4 (2022)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Mercury (Cambridge Crystallographic Data Centre, 2019)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)'
_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)+(0.0210P)²+0.6739P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic-phasing
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4192
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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 0.60036(15) 0.57879(9) 0.26367(9) 0.0276(2) Uani 1 1 d . . . . .
O2 O 0.74196(14) 0.70952(10) 0.19778(8) 0.0265(2) Uani 1 1 d . . . . .
O3 O 0.91443(16) 0.85279(10) 0.39764(9) 0.0336(3) Uani 1 1 d . . . . .
O4 O 0.26340(15) 0.72534(10) 0.41333(8) 0.0286(2) Uani 1 1 d . . . . .
O5 O 0.33388(14) 0.79190(9) 0.28100(8) 0.0237(2) Uani 1 1 d . . . . .
O6 O 0.15585(15) 0.57823(10) 0.12383(8) 0.0295(2) Uani 1 1 d . . . . .
N1 N 0.75663(16) 0.72984(11) 0.47097(10) 0.0214(2) Uani 1 1 d . . . . .
N2 N 0.55679(16) 0.55588(11) 0.51069(10) 0.0221(3) Uani 1 1 d . . . . .
N3 N 0.05195(16) 0.52122(11) 0.26041(10) 0.0214(3) Uani 1 1 d . . . . .
N4 N -0.00646(16) 0.48826(11) 0.44357(9) 0.0215(3) Uani 1 1 d . . . . .
C1 C 0.70411(19) 0.67061(13) 0.27597(12) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.80738(19) 0.76307(13) 0.38921(12) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.80423(18) 0.79448(12) 0.58683(12) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.9217(2) 0.90816(13) 0.63452(13) 0.0240(3) Uani 1 1 d . . . . .
C5 C 0.9563(2) 0.97144(14) 0.74995(13) 0.0277(3) Uani 1 1 d . . . . .
C6 C 0.8789(2) 0.92215(15) 0.81930(13) 0.0283(3) Uani 1 1 d . . . . .
C7 C 0.7666(2) 0.80749(14) 0.77219(13) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.72637(19) 0.74191(13) 0.65662(12) 0.0212(3) Uani 1 1 d . . . . .
C9 C 0.60648(19) 0.62203(13) 0.61525(12) 0.0212(3) Uani 1 1 d . . . . .
C10 C 0.6418(2) 0.63387(16) 0.08798(13) 0.0305(3) Uani 1 1 d . . . . .
C11 C 0.6727(3) 0.70633(19) 0.01848(15) 0.0375(4) Uani 1 1 d . . . . .
C12 C 0.25530(19) 0.71174(13) 0.31805(12) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.14903(19) 0.59526(13) 0.22057(12) 0.0215(3) Uani 1 1 d . . . . .
C14 C -0.06555(19) 0.40785(13) 0.20029(12) 0.0211(3) Uani 1 1 d . . . . .
C15 C -0.1071(2) 0.35855(14) 0.08505(12) 0.0249(3) Uani 1 1 d . . . . .
C16 C -0.2220(2) 0.24575(15) 0.02933(13) 0.0290(3) Uani 1 1 d . . . . .
C17 C -0.2987(2) 0.18102(15) 0.08753(14) 0.0304(3) Uani 1 1 d . . . . .
C18 C -0.2612(2) 0.23056(14) 0.20215(13) 0.0260(3) Uani 1 1 d . . . . .
C19 C -0.14501(19) 0.34365(13) 0.26106(12) 0.0212(3) Uani 1 1 d . . . . .
C20 C -0.11296(19) 0.38688(13) 0.38142(12) 0.0211(3) Uani 1 1 d . . . . .
C21 C 0.4257(2) 0.90944(14) 0.36920(13) 0.0258(3) Uani 1 1 d . . . . .
C22 C 0.5250(2) 0.98492(15) 0.31580(15) 0.0306(3) Uani 1 1 d . . . . .
H1 H 0.564(2) 0.5948(16) 0.6719(15) 0.029(4) Uiso 1 1 d . . . . .
H2 H 0.714(2) 0.7715(16) 0.8204(14) 0.027(4) Uiso 1 1 d . . . . .
H3 H 0.906(2) 0.9665(16) 0.9005(15) 0.028(4) Uiso 1 1 d . . . . .
H4 H 1.035(2) 1.0520(17) 0.7815(14) 0.030(5) Uiso 1 1 d . . . . .
H5 H 0.976(2) 0.9422(16) 0.5875(14) 0.028(4) Uiso 1 1 d . . . . .
H6 H 0.675(3) 0.6583(19) 0.4496(16) 0.040(5) Uiso 1 1 d . . . . .
H7 H 0.510(3) 0.6203(16) 0.0964(14) 0.028(4) Uiso 1 1 d . . . . .
H8 H 0.683(2) 0.5524(17) 0.0579(15) 0.030(5) Uiso 1 1 d . . . . .
H9 H 0.621(3) 0.7902(19) 0.0542(16) 0.041(5) Uiso 1 1 d . . . . .
H10 H 0.603(3) 0.654(2) -0.0590(19) 0.052(6) Uiso 1 1 d . . . . .
H11 H 0.809(3) 0.724(2) 0.0116(18) 0.052(6) Uiso 1 1 d . . . . .
H12 H -0.173(2) 0.3360(15) 0.4154(13) 0.021(4) Uiso 1 1 d . . . . .
H13 H -0.315(2) 0.1876(16) 0.2440(14) 0.025(4) Uiso 1 1 d . . . . .
H14 H -0.381(2) 0.1016(17) 0.0473(15) 0.031(5) Uiso 1 1 d . . . . .
H15 H -0.251(2) 0.2123(16) -0.0524(15) 0.029(4) Uiso 1 1 d . . . . .
H16 H -0.054(2) 0.4027(16) 0.0434(14) 0.027(4) Uiso 1 1 d . . . . .
H17 H 0.073(3) 0.5463(17) 0.3341(17) 0.035(5) Uiso 1 1 d . . . . .
H18 H 0.508(2) 0.8870(15) 0.4191(14) 0.022(4) Uiso 1 1 d . . . . .
H19 H 0.333(2) 0.9524(16) 0.4150(14) 0.024(4) Uiso 1 1 d . . . . .
H20 H 0.623(3) 0.9371(19) 0.2698(17) 0.045(6) Uiso 1 1 d . . . . .
H21 H 0.583(3) 1.070(2) 0.3769(17) 0.044(5) Uiso 1 1 d . . . . .
H22 H 0.439(3) 1.0044(17) 0.2666(15) 0.033(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 1.2057(17) . ?
O2 C1 1.3236(17) . ?
O2 C10 1.4641(19) . ?
O3 C2 1.2144(17) . ?
O4 C12 1.2008(17) . ?
O5 C12 1.3286(16) . ?
O5 C21 1.4592(17) . ?
O6 C13 1.2147(17) . ?
N1 C2 1.3496(18) . ?
N1 C3 1.4068(18) . ?
N1 H6 0.92(2) . ?
N2 C9 1.2863(19) . ?
N2 N2 1.399(2) 2_666 ?
N3 C13 1.3558(18) . ?
N3 C14 1.4083(18) . ?
N3 H17 0.89(2) . ?
N4 C20 1.2850(19) . ?
N4 N4 1.398(2) 2_566 ?
C1 C2 1.543(2) . ?
C3 C4 1.397(2) . ?
C3 C8 1.4197(19) . ?
C4 C5 1.390(2) . ?
C4 H5 0.952(18) . ?
C5 C6 1.388(2) . ?
C5 H4 0.974(18) . ?
C6 C7 1.386(2) . ?
C6 H3 0.980(18) . ?
C7 C8 1.397(2) . ?
C7 H2 0.975(18) . ?
C8 C9 1.4599(19) . ?
C9 H1 0.983(18) . ?
C10 C11 1.503(2) . ?
C10 H7 0.993(18) . ?
C10 H8 0.965(18) . ?
C11 H9 1.03(2) . ?
C11 H10 1.03(2) . ?
C11 H11 1.03(2) . ?
C12 C13 1.541(2) . ?
C14 C15 1.393(2) . ?
C14 C19 1.4206(19) . ?
C15 C16 1.387(2) . ?
C15 H16 0.971(18) . ?
C16 C17 1.390(2) . ?
C16 H15 0.989(18) . ?
C17 C18 1.382(2) . ?
C17 H14 0.983(18) . ?
C18 C19 1.399(2) . ?
C18 H13 0.964(17) . ?
C19 C20 1.455(2) . ?
C20 H12 0.973(17) . ?
C21 C22 1.504(2) . ?
C21 H18 1.012(17) . ?
C21 H19 0.979(18) . ?
C22 H20 1.03(2) . ?
C22 H21 1.02(2) . ?
C22 H22 1.002(19) . ?

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 O2 C10 115.25(12) . . ?
C12 O5 C21 113.96(11) . . ?
C2 N1 C3 128.74(12) . . ?
C2 N1 H6 116.5(12) . . ?
C3 N1 H6 114.6(12) . . ?
C9 N2 N2 112.95(14) . 2_666 ?
C13 N3 C14 128.49(12) . . ?
C13 N3 H17 114.1(12) . . ?
C14 N3 H17 117.2(12) . . ?
C20 N4 N4 113.17(14) . 2_566 ?
O1 C1 O2 126.14(14) . . ?
O1 C1 C2 123.59(13) . . ?
O2 C1 C2 110.24(11) . . ?
O3 C2 N1 128.01(14) . . ?
O3 C2 C1 121.61(13) . . ?
N1 C2 C1 110.36(12) . . ?
C4 C3 N1 122.36(13) . . ?
C4 C3 C8 119.64(13) . . ?
N1 C3 C8 117.99(12) . . ?
C5 C4 C3 119.92(14) . . ?
C5 C4 H5 120.5(11) . . ?
C3 C4 H5 119.6(11) . . ?
C6 C5 C4 121.04(14) . . ?
C6 C5 H4 120.4(10) . . ?
C4 C5 H4 118.6(10) . . ?
C7 C6 C5 119.21(14) . . ?
C7 C6 H3 120.2(10) . . ?
C5 C6 H3 120.6(10) . . ?
C6 C7 C8 121.45(14) . . ?
C6 C7 H2 119.6(10) . . ?
C8 C7 H2 118.9(10) . . ?
C7 C8 C3 118.69(13) . . ?
C7 C8 C9 117.28(13) . . ?
C3 C8 C9 124.03(13) . . ?
N2 C9 C8 122.31(12) . . ?
N2 C9 H1 121.4(10) . . ?
C8 C9 H1 116.3(10) . . ?
O2 C10 C11 107.28(13) . . ?
O2 C10 H7 109.5(10) . . ?
C11 C10 H7 110.0(10) . . ?
O2 C10 H8 108.2(11) . . ?
C11 C10 H8 114.5(11) . . ?
H7 C10 H8 107.3(14) . . ?
C10 C11 H9 109.8(11) . . ?
C10 C11 H10 108.0(12) . . ?
H9 C11 H10 108.1(16) . . ?
C10 C11 H11 110.8(12) . . ?
H9 C11 H11 109.3(16) . . ?
H10 C11 H11 110.7(17) . . ?
O4 C12 O5 126.15(13) . . ?
O4 C12 C13 123.38(13) . . ?
O5 C12 C13 110.47(11) . . ?
O6 C13 N3 127.76(13) . . ?
O6 C13 C12 122.20(12) . . ?
N3 C13 C12 110.04(11) . . ?
C15 C14 N3 122.39(13) . . ?
C15 C14 C19 119.69(13) . . ?
N3 C14 C19 117.91(12) . . ?
C16 C15 C14 120.28(14) . . ?
C16 C15 H16 119.8(10) . . ?
C14 C15 H16 119.9(10) . . ?
C15 C16 C17 120.63(14) . . ?
C15 C16 H15 119.4(10) . . ?
C17 C16 H15 119.9(10) . . ?
C18 C17 C16 119.46(14) . . ?
C18 C17 H14 120.6(11) . . ?
C16 C17 H14 120.0(11) . . ?
C17 C18 C19 121.49(14) . . ?
C17 C18 H13 120.6(10) . . ?
C19 C18 H13 118.0(10) . . ?
C18 C19 C14 118.42(13) . . ?
C18 C19 C20 117.13(13) . . ?
C14 C19 C20 124.45(13) . . ?
N4 C20 C19 122.45(12) . . ?
N4 C20 H12 119.2(9) . . ?
C19 C20 H12 118.3(9) . . ?
O5 C21 C22 108.44(12) . . ?
O5 C21 H18 107.5(9) . . ?
C22 C21 H18 113.9(10) . . ?
O5 C21 H19 107.5(10) . . ?
C22 C21 H19 113.0(10) . . ?
H18 C21 H19 106.3(13) . . ?
C21 C22 H20 110.4(11) . . ?
C21 C22 H21 108.9(11) . . ?
H20 C22 H21 110.2(16) . . ?
C21 C22 H22 111.3(11) . . ?
H20 C22 H22 109.7(15) . . ?
H21 C22 H22 106.3(15) . . ?

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
C10 O2 C1 O1 2.0(2) . . . . ?
C10 O2 C1 C2 -175.91(12) . . . . ?
C3 N1 C2 O3 4.9(2) . . . . ?
C3 N1 C2 C1 -173.52(12) . . . . ?
O1 C1 C2 O3 178.06(14) . . . . ?
O2 C1 C2 O3 -3.98(19) . . . . ?
O1 C1 C2 N1 -3.44(19) . . . . ?
O2 C1 C2 N1 174.52(12) . . . . ?
C2 N1 C3 C4 -1.5(2) . . . . ?
C2 N1 C3 C8 177.46(13) . . . . ?
N1 C3 C4 C5 176.51(13) . . . . ?
C8 C3 C4 C5 -2.4(2) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
C6 C7 C8 C3 0.5(2) . . . . ?
C6 C7 C8 C9 -179.91(13) . . . . ?
C4 C3 C8 C7 1.5(2) . . . . ?
N1 C3 C8 C7 -177.48(12) . . . . ?
C4 C3 C8 C9 -178.12(13) . . . . ?
N1 C3 C8 C9 2.9(2) . . . . ?
N2 N2 C9 C8 179.52(14) 2_666 . . . ?
C7 C8 C9 N2 178.02(13) . . . . ?
C3 C8 C9 N2 -2.4(2) . . . . ?
C1 O2 C10 C11 168.48(13) . . . . ?
C21 O5 C12 O4 -4.6(2) . . . . ?
C21 O5 C12 C13 175.48(11) . . . . ?
C14 N3 C13 O6 -0.7(3) . . . . ?
C14 N3 C13 C12 178.70(13) . . . . ?
O4 C12 C13 O6 -173.33(15) . . . . ?
O5 C12 C13 O6 6.64(19) . . . . ?
O4 C12 C13 N3 7.2(2) . . . . ?
O5 C12 C13 N3 -172.81(12) . . . . ?
C13 N3 C14 C15 -4.1(2) . . . . ?
C13 N3 C14 C19 176.73(13) . . . . ?
N3 C14 C15 C16 179.25(14) . . . . ?
C19 C14 C15 C16 -1.6(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C17 C18 C19 C14 0.2(2) . . . . ?
C17 C18 C19 C20 -179.33(14) . . . . ?
C15 C14 C19 C18 1.1(2) . . . . ?
N3 C14 C19 C18 -179.65(13) . . . . ?
C15 C14 C19 C20 -179.38(13) . . . . ?
N3 C14 C19 C20 -0.2(2) . . . . ?
N4 N4 C20 C19 -179.36(14) 2_566 . . . ?
C18 C19 C20 N4 178.81(13) . . . . ?
C14 C19 C20 N4 -0.7(2) . . . . ?
C12 O5 C21 C22 173.96(13) . . . . ?

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
C4 H5 O3 0.952(18) 2.390(18) 3.1484(17) 136.4(14) 2_776 yes
N1 H6 N2 0.92(2) 1.88(2) 2.6436(16) 140.0(17) . yes
C15 H16 O6 0.971(18) 2.413(18) 3.1644(18) 133.9(13) 2_565 yes
N3 H17 N4 0.89(2) 1.931(19) 2.6552(16) 136.9(17) . yes

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_NN-H4oba
_database_code_depnum_ccdc_archive 'CCDC 2478689'
loop_
_audit_author_name
_audit_author_address
'Grazielli da Rocha'
;UFPR
Brazil
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     (C18H14N4O6)(C2H6OS4)
_chemical_formula_moiety         'C18 H14 N4 O6, 4(C2 H6 O S)'
_chemical_formula_sum            'C26 H38 N4 O10 S4'
_chemical_formula_weight         694.8607

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.269(4)
_cell_length_b                   5.3039(6)
_cell_length_c                   24.374(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.583(15)
_cell_angle_gamma                90
_cell_volume                     1652.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9554
_cell_measurement_theta_min      3.7594
_cell_measurement_theta_max      74.1966

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.798
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.152
_exptl_absorpt_coefficient_mu    3.144
_shelx_estimated_absorpt_T_min   0.188
_shelx_estimated_absorpt_T_max   0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3634
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            73279
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.458
_diffrn_reflns_theta_max         70.952
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3183
_reflns_number_gt                3106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX4 (2022)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'Mercury (Cambridge Crystallographic Data Centre, 2019)'
_computing_publication_material  
'SHELXL-97 (Sheldrick, 2008) and WINGX (Farrugia, 2012)'
_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)+(0.0516P)²+0.9103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic-phasing
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.89477(2) 0.75453(6) 0.55343(2) 0.01861(12) Uani 1 1 d . . . . .
S2 S 0.81906(3) 1.00167(7) 0.74135(2) 0.02745(13) Uani 1 1 d . . . . .
O1 O 0.73107(8) 0.3327(2) 0.47806(4) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.84810(8) 0.4134(2) 0.42881(4) 0.0224(2) Uani 1 1 d . . . . .
O3 O 0.77091(8) 0.02561(19) 0.35857(4) 0.0229(2) Uani 1 1 d . . . . .
O4 O 0.88589(8) 0.79799(19) 0.49044(4) 0.0215(2) Uani 1 1 d . . . . .
O5 O 0.87223(12) 0.8999(2) 0.69906(5) 0.0435(3) Uani 1 1 d . . . . .
N1 N 0.64861(9) -0.0424(2) 0.40857(5) 0.0186(2) Uani 1 1 d . . . . .
N2 N 0.52118(9) -0.0328(2) 0.47760(5) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.77107(10) 0.2895(3) 0.43959(6) 0.0187(3) Uani 1 1 d . . . . .
C2 C 0.73115(10) 0.0736(3) 0.39690(6) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.58908(10) -0.2425(2) 0.38010(6) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.60992(11) -0.3606(3) 0.33302(6) 0.0204(3) Uani 1 1 d . . . . .
C5 C 0.54849(11) -0.5596(3) 0.30620(6) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.46549(12) -0.6469(3) 0.32563(7) 0.0264(3) Uani 1 1 d . . . . .
C7 C 0.44518(11) -0.5325(3) 0.37248(7) 0.0257(3) Uani 1 1 d . . . . .
C8 C 0.50488(10) -0.3302(3) 0.40054(6) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.47540(11) -0.2243(3) 0.44926(6) 0.0210(3) Uani 1 1 d . . . . .
C10 C 0.96206(12) 1.0232(3) 0.58852(7) 0.0236(3) Uani 1 1 d . . . . .
C11 C 0.76907(11) 0.8238(3) 0.56281(7) 0.0255(3) Uani 1 1 d . . . . .
C12 C 0.91149(17) 0.9997(4) 0.80800(7) 0.0487(5) Uani 1 1 d . . . . .
H15 H 0.879399 1.065367 0.836911 0.073 Uiso 1 1 calc R U . . .
H14 H 0.935630 0.826773 0.817824 0.073 Uiso 1 1 calc R U . . .
H16 H 0.971121 1.106014 0.806515 0.073 Uiso 1 1 calc R U . . .
C13 C 0.8132(2) 1.3340(4) 0.73214(9) 0.0603(7) Uani 1 1 d . . . . .
H17 H 0.778786 1.409490 0.759073 0.091 Uiso 1 1 calc R U . . .
H18 H 0.884247 1.401579 0.739146 0.091 Uiso 1 1 calc R U . . .
H19 H 0.773247 1.374358 0.693116 0.091 Uiso 1 1 calc R U . . .
H1 H 0.8630(19) 0.563(5) 0.4522(11) 0.058(7) Uiso 1 1 d . . . . .
H2 H 0.6288(15) 0.021(4) 0.4367(9) 0.029(5) Uiso 1 1 d . . . . .
H3 H 0.6658(14) -0.306(3) 0.3206(7) 0.024(4) Uiso 1 1 d . . . . .
H4 H 0.5634(15) -0.637(4) 0.2744(8) 0.032(5) Uiso 1 1 d . . . . .
H5 H 0.4241(17) -0.783(4) 0.3072(9) 0.037(5) Uiso 1 1 d . . . . .
H6 H 0.3906(15) -0.592(4) 0.3899(8) 0.034(5) Uiso 1 1 d . . . . .
H7 H 0.4207(13) -0.303(3) 0.4589(7) 0.017(4) Uiso 1 1 d . . . . .
H8 H 1.0315(17) 1.000(4) 0.5891(9) 0.037(5) Uiso 1 1 d . . . . .
H9 H 0.9290(15) 1.174(4) 0.5685(8) 0.030(5) Uiso 1 1 d . . . . .
H10 H 0.9541(14) 1.022(3) 0.6252(9) 0.028(5) Uiso 1 1 d . . . . .
H11 H 0.7482(17) 0.992(4) 0.5474(10) 0.041(6) Uiso 1 1 d . . . . .
H12 H 0.7720(15) 0.824(4) 0.6010(9) 0.034(5) Uiso 1 1 d . . . . .
H13 H 0.7225(16) 0.695(4) 0.5435(9) 0.035(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
S1 O4 1.5254(10) . ?
S1 C10 1.7744(15) . ?
S1 C11 1.7815(15) . ?
S2 O5 1.4974(12) . ?
S2 C12 1.7529(19) . ?
S2 C13 1.776(2) . ?
O1 C1 1.2168(17) . ?
O2 C1 1.2999(17) . ?
O3 C2 1.2169(17) . ?
N1 C2 1.3513(18) . ?
N1 C3 1.3922(18) . ?
N2 C9 1.2853(19) . ?
N2 N2 1.400(2) 3_656 ?
C1 C2 1.5423(19) . ?
C3 C4 1.3984(19) . ?
C3 C8 1.4183(19) . ?
C4 C5 1.385(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.382(2) . ?
C7 C8 1.399(2) . ?
C8 C9 1.4586(19) . ?

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
O4 S1 C10 104.87(7) . . ?
O4 S1 C11 106.03(7) . . ?
C10 S1 C11 98.03(8) . . ?
O5 S2 C12 107.10(9) . . ?
O5 S2 C13 106.47(9) . . ?
C12 S2 C13 96.83(12) . . ?
C2 N1 C3 128.73(12) . . ?
C9 N2 N2 112.65(14) . 3_656 ?
O1 C1 O2 126.16(13) . . ?
O1 C1 C2 121.20(12) . . ?
O2 C1 C2 112.64(11) . . ?
O3 C2 N1 127.55(13) . . ?
O3 C2 C1 122.15(12) . . ?
N1 C2 C1 110.29(11) . . ?
N1 C3 C4 122.66(12) . . ?
N1 C3 C8 118.02(12) . . ?
C4 C3 C8 119.31(13) . . ?
C5 C4 C3 120.48(13) . . ?
C4 C5 C6 120.84(14) . . ?
C7 C6 C5 118.93(14) . . ?
C6 C7 C8 122.03(13) . . ?
C7 C8 C3 118.41(13) . . ?
C7 C8 C9 116.94(12) . . ?
C3 C8 C9 124.65(13) . . ?
N2 C9 C8 123.39(13) . . ?

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 N1 C2 O3 -0.1(2) . . . . ?
C3 N1 C2 C1 179.02(12) . . . . ?
O1 C1 C2 O3 -179.14(13) . . . . ?
O2 C1 C2 O3 1.63(19) . . . . ?
O1 C1 C2 N1 1.69(19) . . . . ?
O2 C1 C2 N1 -177.54(11) . . . . ?
C2 N1 C3 C4 1.3(2) . . . . ?
C2 N1 C3 C8 -179.43(13) . . . . ?
N1 C3 C4 C5 179.85(13) . . . . ?
C8 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C7 C8 C3 -0.4(2) . . . . ?
C6 C7 C8 C9 179.61(14) . . . . ?
N1 C3 C8 C7 -179.49(13) . . . . ?
C4 C3 C8 C7 -0.2(2) . . . . ?
N1 C3 C8 C9 0.5(2) . . . . ?
C4 C3 C8 C9 179.73(13) . . . . ?
N2 N2 C9 C8 -179.97(14) 3_656 . . . ?
C7 C8 C9 N2 -177.49(14) . . . . ?
C3 C8 C9 N2 2.6(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
C12 H16 O5 0.98 2.63 3.611(3) 178.5 2_756 yes
N1 H2 N2 0.86(2) 1.97(2) 2.6871(17) 139.7(17) . yes
C11 H11 O1 0.98(2) 2.44(2) 3.354(2) 154.7(17) 1_565 yes
C11 H13 O1 0.96(2) 2.52(2) 3.2779(19) 136.4(15) . yes
C12 H15 O2 0.98 2.39 3.305(2) 155.5 4_576 yes
C13 H17 O3 0.98 2.48 3.361(2) 149.5 4_576 yes
O2 H1 O4 0.96(3) 1.54(3) 2.5030(14) 179(2) . yes
C10 H8 O3 0.93(2) 2.59(2) 3.439(2) 152.2(17) 3_766 yes
C10 H10 O5 0.93(2) 2.43(2) 3.291(2) 155.0(16) . yes
C11 H12 O5 0.92(2) 2.44(2) 3.259(2) 148.8(16) . yes

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.061

