# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_777_auto
_database_code_depnum_ccdc_archive 'CCDC 2518010'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-10-11
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O2, C8 H9 N3 O3'
_chemical_formula_sum            'C17 H20 N4 O5'
_chemical_formula_weight         360.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H20N4O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.7360(4)
_cell_length_b                   4.91439(11)
_cell_length_c                   21.9254(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.240(2)
_cell_angle_gamma                90
_cell_volume                     1784.68(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2846
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      75.2420
_cell_measurement_theta_min      4.0570
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.004
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13114
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.512
_diffrn_reflns_theta_min         3.116
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -94.00 -67.00   0.50   25.00    --  -50.59-142.00  67.00   54
  2  ω    -98.00 -49.00   0.50   25.00    --  -50.59 142.00 124.00   98
  3  ω   -106.00 -79.00   0.50   25.00    --  -50.59-128.00-121.00   54
  4  ω     49.00  84.00   0.50   25.00    --   50.59-142.00  67.00   70
  5  ω   -115.00 -73.00   0.50   25.00    --  -50.59-125.00  90.00   84
  6  ω    -93.00 -46.00   0.50   25.00    --  -50.59   0.00   0.00   94
  7  ω    -20.00  21.00   0.50   25.00    --  -50.59  19.00-120.00   82
  8  ω     42.00  67.00   0.50   25.00    --   50.59-128.00-121.00   50
  9  ω     -7.00  25.00   0.50   25.00    --   50.59 -19.00-120.00   64
 10  ω     -8.00  25.00   0.50   25.00    --   50.59 -19.00-150.00   66
 11  ω   -109.00 -84.00   0.50  130.00    --  -90.00-142.00  67.00   50
 12  ω   -149.00 -78.00   0.50  130.00    --  -90.00-128.00-121.00  142
 13  ω    -43.00 -18.00   0.50  130.00    --  -90.00  45.00-180.00   50
 14  ω    -51.00 -25.00   0.50  130.00    --  -90.00  45.00 -30.00   52
 15  ω     43.00 114.00   0.50  130.00    --  111.50-128.00-121.00  142
 16  ω     78.00 124.00   0.50  130.00    --  111.50-142.00  67.00   92
 17  ω    111.00 136.00   0.50  130.00    --  111.50 128.00 -46.00   50
 18  ω    104.00 129.00   0.50  130.00    --  111.50 142.00 124.00   50
 19  ω     46.00  72.00   0.50  130.00    --  111.50-142.00  67.00   52
 20  ω     41.00  66.00   0.50  130.00    --  111.50 -61.00   0.00   50
 21  ω     78.00 104.00   0.50  130.00    --  111.50 -94.00-150.00   52
 22  ω    144.00 171.00   0.50  130.00    --  111.50  45.00-120.00   54
 23  ω     41.00  66.00   0.50  130.00    --  111.50 -61.00-120.00   50
 24  ω    108.00 143.00   0.50  130.00    --  111.50  45.00-120.00   70
 25  ω     43.00  84.00   0.50  130.00    --  111.50 -94.00-120.00   82
 26  ω    140.00 178.00   0.50  130.00    --  111.50 125.00  60.00   76
 27  ω     42.00  70.00   0.50  130.00    --  111.50 -61.00 -60.00   56
 28  ω     98.00 134.00   0.50  130.00    --  111.50 125.00  60.00   72
 29  ω     73.00 106.00   0.50  130.00    --  111.50 -94.00  60.00   66
 30  ω     42.00  67.00   0.50  130.00    --  111.50 -61.00  60.00   50
 31  ω    125.00 163.00   0.50  130.00    --  111.50  77.00 -60.00   76
 32  ω     83.00 108.00   0.50  130.00    --  111.50-112.00 -98.25   50
 33  ω     85.00 111.00   0.50  130.00    --  111.50-125.00   0.00   52
 34  ω     45.00  71.00   0.50  130.00    --  111.50 -94.00  60.00   52
 35  ω     65.00 107.00   0.50  130.00    --  111.50   0.00 120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0644331000
_diffrn_orient_matrix_UB_12      -0.0319369000
_diffrn_orient_matrix_UB_13      0.0430812000
_diffrn_orient_matrix_UB_21      -0.0032341000
_diffrn_orient_matrix_UB_22      0.3115092000
_diffrn_orient_matrix_UB_23      0.0072804000
_diffrn_orient_matrix_UB_31      -0.0669514000
_diffrn_orient_matrix_UB_32      0.0159335000
_diffrn_orient_matrix_UB_33      -0.0559792000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2689
_reflns_number_total             3662
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0016(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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.039
_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)+(0.0860P)²+0.2496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1508
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59281(9) 0.2047(3) 0.77563(7) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.66423(9) 0.0553(4) 0.78499(8) 0.0417(4) Uani 1 1 d . . . . .
H2 H 0.705658 0.086244 0.760369 0.050 Uiso 1 1 calc R U . . .
C3 C 0.67328(10) -0.1393(4) 0.83109(8) 0.0466(4) Uani 1 1 d . . . . .
H3 H 0.721506 -0.243697 0.838000 0.056 Uiso 1 1 calc R U . . .
C4 C 0.61351(11) -0.1844(4) 0.86717(8) 0.0480(4) Uani 1 1 d . . . . .
H4 H 0.621371 -0.318833 0.898598 0.058 Uiso 1 1 calc R U . . .
C5 C 0.54116(10) -0.0349(4) 0.85826(8) 0.0489(4) Uani 1 1 d . . . . .
C6 C 0.53243(10) 0.1611(4) 0.81144(8) 0.0438(4) Uani 1 1 d . . . . .
H6 H 0.484267 0.265666 0.804169 0.053 Uiso 1 1 calc R U . . .
C7 C 0.57972(9) 0.4173(3) 0.72703(7) 0.0384(4) Uani 1 1 d . . . . .
C11 C 0.40101(13) 0.0104(7) 0.87431(13) 0.0848(8) Uani 1 1 d . . . . .
H11A H 0.399549 0.209394 0.871505 0.127 Uiso 1 1 calc R U . . .
H11B H 0.365818 -0.050369 0.903708 0.127 Uiso 1 1 calc R U . . .
H11C H 0.382231 -0.067991 0.833682 0.127 Uiso 1 1 calc R U . . .
C12 C 0.49506(16) -0.2798(6) 0.94319(12) 0.0807(7) Uani 1 1 d . . . . .
H12A H 0.500436 -0.459583 0.924864 0.121 Uiso 1 1 calc R U . . .
H12B H 0.449160 -0.280729 0.966371 0.121 Uiso 1 1 calc R U . . .
H12C H 0.544569 -0.236238 0.971043 0.121 Uiso 1 1 calc R U . . .
C14 C 0.56350(11) 1.0108(3) 0.59181(8) 0.0464(4) Uani 1 1 d . . . . .
C15 C 0.56550(13) 1.2055(4) 0.54519(8) 0.0545(5) Uani 1 1 d . . . . .
H15 H 0.522766 1.332709 0.535809 0.065 Uiso 1 1 calc R U . . .
C16 C 0.63048(13) 1.2083(4) 0.51346(8) 0.0578(5) Uani 1 1 d . . . . .
H16 H 0.633456 1.336032 0.481347 0.069 Uiso 1 1 calc R U . . .
C17 C 0.69141(12) 1.0211(4) 0.52933(8) 0.0530(5) Uani 1 1 d . . . . .
C18 C 0.68705(12) 0.8384(4) 0.57601(8) 0.0498(4) Uani 1 1 d . . . . .
H18 H 0.729945 0.712656 0.586450 0.060 Uiso 1 1 calc R U . . .
C20 C 0.43126(11) 1.1327(4) 0.62332(9) 0.0521(5) Uani 1 1 d . . . . .
C21 C 0.37648(12) 1.0364(4) 0.66742(11) 0.0601(5) Uani 1 1 d . . . . .
H21A H 0.409757 0.984345 0.706715 0.072 Uiso 1 1 calc R U . . .
H21B H 0.347550 0.871634 0.650210 0.072 Uiso 1 1 calc R U . . .
C22 C 0.31543(17) 1.2455(7) 0.68053(16) 0.0960(9) Uani 1 1 d . . . . .
H22A H 0.284712 1.307981 0.641625 0.144 Uiso 1 1 calc R U . . .
H22B H 0.343354 1.400426 0.702222 0.144 Uiso 1 1 calc R U . . .
H22C H 0.278478 1.164290 0.706273 0.144 Uiso 1 1 calc R U . . .
N10 N 0.48175(11) -0.0768(5) 0.89475(9) 0.0735(6) Uani 1 1 d . . . . .
N13 N 0.62414(9) 0.8325(3) 0.60718(6) 0.0471(4) Uani 1 1 d . . . . .
N19 N 0.50118(9) 0.9816(3) 0.62619(7) 0.0481(4) Uani 1 1 d . . . . .
H19 H 0.5080(12) 0.843(4) 0.6545(10) 0.049(5) Uiso 1 1 d . . . . .
N24 N 0.76042(12) 1.0106(5) 0.49579(8) 0.0680(5) Uani 1 1 d . . . . .
O8 O 0.64082(7) 0.4433(3) 0.69506(6) 0.0461(3) Uani 1 1 d . . . . .
H8 H 0.6298(16) 0.595(6) 0.6673(13) 0.083(8) Uiso 1 1 d . . . . .
O9 O 0.51817(7) 0.5525(3) 0.71630(6) 0.0473(3) Uani 1 1 d . . . . .
O23 O 0.41534(9) 1.3218(3) 0.58789(7) 0.0676(4) Uani 1 1 d . . . . .
O25 O 0.81107(12) 0.8378(5) 0.51010(9) 0.0915(6) Uani 1 1 d . . . . .
O26 O 0.76417(12) 1.1749(5) 0.45494(9) 0.1039(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(2) . ?
C1 C6 1.382(2) . ?
C1 C7 1.486(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.379(2) . ?
C4 C5 1.406(3) . ?
C5 C6 1.400(2) . ?
C5 N10 1.378(2) . ?
C7 O8 1.326(2) . ?
C7 O9 1.2200(19) . ?
C11 N10 1.427(3) . ?
C12 N10 1.451(3) . ?
C14 C15 1.404(3) . ?
C14 N13 1.346(2) . ?
C14 N19 1.379(2) . ?
C15 C16 1.372(3) . ?
C16 C17 1.380(3) . ?
C17 C18 1.371(3) . ?
C17 N24 1.456(3) . ?
C18 N13 1.335(2) . ?
C20 C21 1.501(3) . ?
C20 N19 1.380(2) . ?
C20 O23 1.216(2) . ?
C21 C22 1.506(3) . ?
N24 O25 1.209(3) . ?
N24 O26 1.214(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 120.76(15) . . ?
C6 C1 C2 121.08(15) . . ?
C6 C1 C7 118.15(14) . . ?
C3 C2 C1 118.28(16) . . ?
C4 C3 C2 121.16(15) . . ?
C3 C4 C5 121.15(16) . . ?
C6 C5 C4 117.31(16) . . ?
N10 C5 C4 121.34(17) . . ?
N10 C5 C6 121.34(17) . . ?
C1 C6 C5 121.01(15) . . ?
O8 C7 C1 113.65(13) . . ?
O9 C7 C1 123.69(15) . . ?
O9 C7 O8 122.64(14) . . ?
N13 C14 C15 121.99(19) . . ?
N13 C14 N19 113.43(15) . . ?
N19 C14 C15 124.58(17) . . ?
C16 C15 C14 118.63(18) . . ?
C15 C16 C17 118.43(17) . . ?
C16 C17 N24 120.47(18) . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 N24 119.0(2) . . ?
N13 C18 C17 121.77(18) . . ?
N19 C20 C21 113.14(16) . . ?
O23 C20 C21 123.66(18) . . ?
O23 C20 N19 123.2(2) . . ?
C20 C21 C22 113.67(19) . . ?
C5 N10 C11 120.16(18) . . ?
C5 N10 C12 118.66(18) . . ?
C11 N10 C12 118.38(19) . . ?
C18 N13 C14 118.64(15) . . ?
C14 N19 C20 128.47(16) . . ?
O25 N24 C17 118.11(18) . . ?
O25 N24 O26 123.4(2) . . ?
O26 N24 C17 118.5(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
N19 H19 O9 0.92(2) 1.96(2) 2.8760(19) 177.5(19) . yes
O8 H8 N13 0.96(3) 1.75(3) 2.7009(18) 167(2) . yes

_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.470
####################################################################### 
# 
# 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_782a
_database_code_depnum_ccdc_archive 'CCDC 2518018'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N O2, 2(C11 H15 N3 O3)'
_chemical_formula_sum            'C29 H37 N7 O8'
_chemical_formula_weight         611.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H22N4O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   20.1578(5)
_cell_length_b                   4.90086(14)
_cell_length_c                   32.5043(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.875(2)
_cell_angle_gamma                90
_cell_volume                     3210.75(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5365
_cell_measurement_temperature    297(1)
_cell_measurement_theta_max      74.4010
_cell_measurement_theta_min      2.5800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            24768
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.442
_diffrn_reflns_theta_min         2.562
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  21.00   0.50   60.00    --  -50.71  61.00  -9.00  168
  2  ω   -119.00 -37.00   0.50   60.00    --  -50.71 -61.00-148.00  164
  3  ω     55.00  80.00   0.50   60.00    --   50.71  61.00  -9.00   50
  4  ω      2.00  27.00   0.50   60.00    --   50.71 -61.00-148.00   50
  5  ω   -159.00-131.00   0.50  250.00    --  -90.00 -61.00-148.00   56
  6  ω    -71.00 -19.00   0.50  250.00    --  -90.00  61.00  -9.00  104
  7  ω     38.00  70.00   0.50  250.00    --  106.85 -61.00-148.00   64
  8  ω    110.00 178.00   0.50  250.00    --  106.85  61.00  -9.00  136
  9  ω   -100.00 -75.00   0.50   60.00    --  -50.71-125.00 120.00   50
 10  ω   -118.00 -73.00   0.50   60.00    --  -50.71-125.00   0.00   90
 11  ω   -138.00 -91.00   0.50  250.00    --  -90.00   0.00  60.00   94
 12  ω   -160.00-131.00   0.50  250.00    --  -90.00 -57.00 -90.00   58
 13  ω    -58.00 -18.00   0.50  250.00    --  -90.00  77.00  60.00   80
 14  ω   -104.00 -78.00   0.50  250.00    --  -90.00  77.00  60.00   52
 15  ω     40.00  65.00   0.50  250.00    --  106.85 -57.00  90.00   50
 16  ω     35.00  62.00   0.50  250.00    --  106.85 -57.00 -90.00   54
 17  ω     35.00  62.00   0.50  250.00    --  106.85 -57.00  60.00   54
 18  ω     39.00  66.00   0.50  250.00    --  106.85 -57.00 150.00   54
 19  ω     66.00 113.00   0.50  250.00    --  106.85   0.00 -30.00   94
 20  ω     35.00  66.00   0.50  250.00    --  106.85 -57.00-120.00   62
 21  ω     35.00  60.00   0.50  250.00    --  106.85 -57.00-150.00   50
 22  ω     35.00  89.00   0.50  250.00    --  106.85 -77.00  30.00  108
 23  ω    149.00 174.00   0.50  250.00    --  106.85 125.00  30.00   50
 24  ω     97.00 141.00   0.50  250.00    --  106.85 125.00  30.00   88
 25  ω    124.00 163.00   0.50  250.00    --  106.85  57.00 -90.00   78
 26  ω     81.00 107.00   0.50  250.00    --  106.85   0.00-150.00   52
 27  ω     41.00  66.00   0.50  250.00    --  106.85 -57.00  30.00   50
 28  ω     52.00  77.00   0.50   60.00    --   50.58  77.00-180.00   50
 29  ω    -56.00 -46.00   0.50  250.00    --  -90.00  57.00  30.00   20
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0241416000
_diffrn_orient_matrix_UB_12      0.0419673000
_diffrn_orient_matrix_UB_13      -0.0443031000
_diffrn_orient_matrix_UB_21      0.0535374000
_diffrn_orient_matrix_UB_22      -0.2203136000
_diffrn_orient_matrix_UB_23      0.0069292000
_diffrn_orient_matrix_UB_31      -0.0489119000
_diffrn_orient_matrix_UB_32      -0.2202642000
_diffrn_orient_matrix_UB_33      -0.0153711000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3585
_reflns_number_total             6488
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.018
_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)+(0.0861P)²+0.2462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1726
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B),
 C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C12(H12), C13(H13), C26(H26), C27(H27),
 C29(H29)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60671(12) 1.3073(5) 0.31152(8) 0.0870(7) Uani 1 1 d . . . . .
H1 H 0.569741 1.196100 0.307728 0.104 Uiso 1 1 calc R U . . .
C2 C 0.64442(10) 1.2855(4) 0.34725(7) 0.0695(5) Uani 1 1 d . . . . .
C3 C 0.69887(11) 1.4563(4) 0.35202(7) 0.0751(6) Uani 1 1 d . . . . .
H3 H 0.725008 1.444278 0.375779 0.090 Uiso 1 1 calc R U . . .
C4 C 0.71471(12) 1.6417(5) 0.32247(7) 0.0807(6) Uani 1 1 d . . . . .
H4 H 0.750866 1.756808 0.326631 0.097 Uiso 1 1 calc R U . . .
C5 C 0.67775(12) 1.6607(5) 0.28637(7) 0.0817(6) Uani 1 1 d . . . . .
C6 C 0.62332(14) 1.4917(6) 0.28154(8) 0.0944(8) Uani 1 1 d . . . . .
H6 H 0.597529 1.502963 0.257632 0.113 Uiso 1 1 calc R U . . .
C7 C 0.62658(11) 1.0799(4) 0.37777(7) 0.0700(5) Uani 1 1 d . . . . .
C8 C 0.2778(2) 0.4106(13) 0.33479(18) 0.213(3) Uani 1 1 d . . . . .
H8A H 0.281767 0.219297 0.327557 0.256 Uiso 1 1 calc R U . . .
H8B H 0.251826 0.420270 0.359628 0.256 Uiso 1 1 calc R U . . .
O8 O 0.57510(8) 0.9502(3) 0.37674(5) 0.0877(5) Uani 1 1 d . . . . .
C9 C 0.2414(3) 0.5444(16) 0.3026(2) 0.280(4) Uani 1 1 d . . . . .
H9A H 0.269422 0.568934 0.279267 0.420 Uiso 1 1 calc R U . . .
H9B H 0.226473 0.719149 0.312084 0.420 Uiso 1 1 calc R U . . .
H9C H 0.203719 0.435130 0.294745 0.420 Uiso 1 1 calc R U . . .
O9 O 0.67209(8) 1.0446(3) 0.40728(5) 0.0780(4) Uani 1 1 d . . . . .
H9 H 0.6598(15) 0.912(7) 0.4229(10) 0.122(11) Uiso 1 1 d . . . . .
C10 C 0.9617(3) 0.9752(15) 0.70577(14) 0.215(3) Uani 1 1 d . . . . .
H10A H 0.946866 1.159721 0.711282 0.258 Uiso 1 1 calc R U . . .
H10B H 1.008943 0.983870 0.700636 0.258 Uiso 1 1 calc R U . . .
N10 N 0.6975(2) 1.8327(6) 0.25537(9) 0.1086(8) Uani 1 1 d . . . . .
H10C H 0.6675(17) 1.871(7) 0.2368(11) 0.133(14) Uiso 1 1 d . . . . .
H10D H 0.7260(16) 1.964(8) 0.2615(10) 0.128(13) Uiso 1 1 d . . . . .
C11 C 0.59010(10) 0.4662(4) 0.46188(7) 0.0672(5) Uani 1 1 d . . . . .
C12 C 0.58375(11) 0.2596(4) 0.49111(7) 0.0760(6) Uani 1 1 d . . . . .
H12 H 0.545023 0.156916 0.492279 0.091 Uiso 1 1 calc R U . . .
C13 C 0.63480(11) 0.2104(5) 0.51782(7) 0.0788(6) Uani 1 1 d . . . . .
H13 H 0.631800 0.073563 0.537526 0.095 Uiso 1 1 calc R U . . .
C14 C 0.69129(11) 0.3683(5) 0.51502(7) 0.0770(6) Uani 1 1 d . . . . .
C15 C 0.69476(13) 0.5719(5) 0.48596(7) 0.0762(6) Uani 1 1 d . . . . .
H15 H 0.7309(12) 0.683(5) 0.4832(7) 0.092(7) Uiso 1 1 d . . . . .
N16 N 0.64525(9) 0.6205(3) 0.45970(6) 0.0726(5) Uani 1 1 d . . . . .
C16 C 0.9517(4) 0.809(2) 0.74360(16) 0.330(6) Uani 1 1 d . . . . .
H16A H 0.917046 0.678442 0.738655 0.495 Uiso 1 1 calc R U . . .
H16B H 0.939605 0.926713 0.765872 0.495 Uiso 1 1 calc R U . . .
H16C H 0.992146 0.715232 0.750624 0.495 Uiso 1 1 calc R U . . .
C17 C 0.34439(18) 0.5148(10) 0.34440(14) 0.1618(17) Uani 1 1 d . . . . .
H17A H 0.340028 0.706741 0.351111 0.194 Uiso 1 1 calc R U . . .
H17B H 0.369990 0.504082 0.319425 0.194 Uiso 1 1 calc R U . . .
N17 N 0.54328(9) 0.5289(4) 0.43250(6) 0.0745(5) Uani 1 1 d . . . . .
H17 H 0.5521(11) 0.659(5) 0.4172(7) 0.081(7) Uiso 1 1 d . . . . .
C18 C 0.48437(11) 0.3983(5) 0.42386(7) 0.0783(6) Uani 1 1 d . . . . .
C19 C 0.44835(13) 0.5112(6) 0.38758(9) 0.1026(9) Uani 1 1 d . . . . .
H19A H 0.441456 0.704697 0.392156 0.123 Uiso 1 1 calc R U . . .
H19B H 0.476597 0.493229 0.363838 0.123 Uiso 1 1 calc R U . . .
C20 C 0.38391(16) 0.3867(8) 0.37747(11) 0.1311(12) Uani 1 1 d . . . . .
H20A H 0.357554 0.386167 0.402189 0.157 Uiso 1 1 calc R U . . .
H20B H 0.391541 0.197910 0.369954 0.157 Uiso 1 1 calc R U . . .
O21 O 0.46352(8) 0.2108(4) 0.44450(6) 0.0956(5) Uani 1 1 d . . . . .
N22 N 0.74650(11) 0.3210(5) 0.54304(7) 0.0959(6) Uani 1 1 d . . . . .
O23 O 0.79392(10) 0.4778(4) 0.54247(7) 0.1201(7) Uani 1 1 d . . . . .
O24 O 0.74418(10) 0.1250(5) 0.56596(7) 0.1305(8) Uani 1 1 d . . . . .
C25 C 0.88537(11) 1.0679(5) 0.47966(8) 0.0870(7) Uani 1 1 d . . . . .
C26 C 0.92573(13) 1.2758(6) 0.46594(9) 0.1011(8) Uani 1 1 d . . . . .
H26 H 0.954972 1.364184 0.483886 0.121 Uiso 1 1 calc R U . . .
C27 C 0.92170(13) 1.3484(6) 0.42542(10) 0.1050(9) Uani 1 1 d . . . . .
H27 H 0.947905 1.488470 0.415261 0.126 Uiso 1 1 calc R U . . .
C28 C 0.87866(11) 1.2121(6) 0.40018(9) 0.0930(7) Uani 1 1 d . . . . .
C29 C 0.83887(13) 1.0141(6) 0.41630(10) 0.1059(9) Uani 1 1 d . . . . .
H29 H 0.808844 0.926185 0.398809 0.127 Uiso 1 1 calc R U . . .
N30 N 0.84092(10) 0.9413(5) 0.45545(8) 0.1014(7) Uani 1 1 d . . . . .
N31 N 0.88574(11) 0.9720(5) 0.51966(8) 0.0963(7) Uani 1 1 d . . . . .
H31 H 0.8614(13) 0.857(6) 0.5246(8) 0.089(9) Uiso 1 1 d . . . . .
C32 C 0.91975(12) 1.0683(6) 0.55361(9) 0.0959(8) Uani 1 1 d . . . . .
C33 C 0.90598(15) 0.9194(7) 0.59234(9) 0.1121(9) Uani 1 1 d . . . . .
H33A H 0.858439 0.919557 0.596544 0.135 Uiso 1 1 calc R U . . .
H33B H 0.919740 0.731132 0.589075 0.135 Uiso 1 1 calc R U . . .
C34 C 0.93908(18) 1.0319(9) 0.62976(10) 0.1313(12) Uani 1 1 d . . . . .
H34A H 0.986442 1.039313 0.625029 0.158 Uiso 1 1 calc R U . . .
H34B H 0.923835 1.217716 0.633625 0.158 Uiso 1 1 calc R U . . .
C35 C 0.9281(2) 0.8798(11) 0.66790(11) 0.1621(17) Uani 1 1 d . . . . .
H35A H 0.941353 0.692193 0.663282 0.195 Uiso 1 1 calc R U . . .
H35B H 0.880721 0.878566 0.672836 0.195 Uiso 1 1 calc R U . . .
O36 O 0.95706(10) 1.2616(5) 0.55153(6) 0.1260(7) Uani 1 1 d . . . . .
N37 N 0.87504(12) 1.2749(7) 0.35665(9) 0.1133(8) Uani 1 1 d . . . . .
O38 O 0.90245(15) 1.4791(7) 0.34447(8) 0.1588(10) Uani 1 1 d . . . . .
O39 O 0.84473(13) 1.1237(7) 0.33400(7) 0.1468(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(3) . ?
C1 C6 1.374(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.463(3) . ?
C3 C4 1.363(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.382(3) . ?
C5 N10 1.377(3) . ?
C7 O8 1.217(2) . ?
C7 O9 1.328(3) . ?
C8 C9 1.429(7) . ?
C8 C17 1.466(5) . ?
C10 C16 1.491(8) . ?
C10 C35 1.473(5) . ?
C11 C12 1.396(3) . ?
C11 N16 1.347(3) . ?
C11 N17 1.367(3) . ?
C12 C13 1.358(3) . ?
C13 C14 1.381(3) . ?
C14 C15 1.377(3) . ?
C14 N22 1.446(3) . ?
C15 N16 1.325(3) . ?
C17 C20 1.469(5) . ?
N17 C18 1.374(3) . ?
C18 C19 1.483(4) . ?
C18 O21 1.216(3) . ?
C19 C20 1.468(4) . ?
N22 O23 1.227(3) . ?
N22 O24 1.217(3) . ?
C25 C26 1.382(4) . ?
C25 N30 1.336(3) . ?
C25 N31 1.382(3) . ?
C26 C27 1.365(4) . ?
C27 C28 1.360(4) . ?
C28 C29 1.368(4) . ?
C28 N37 1.449(4) . ?
C29 N30 1.322(4) . ?
N31 C32 1.374(3) . ?
C32 C33 1.485(4) . ?
C32 O36 1.212(3) . ?
C33 C34 1.484(4) . ?
C34 C35 1.466(5) . ?
N37 O38 1.212(3) . ?
N37 O39 1.204(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.7(2) . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 C7 119.0(2) . . ?
C3 C2 C7 122.8(2) . . ?
C4 C3 C2 121.1(2) . . ?
C3 C4 C5 120.9(2) . . ?
C6 C5 C4 118.2(2) . . ?
N10 C5 C4 120.3(3) . . ?
N10 C5 C6 121.5(3) . . ?
C1 C6 C5 121.0(2) . . ?
O8 C7 C2 124.0(2) . . ?
O8 C7 O9 122.1(2) . . ?
O9 C7 C2 113.90(19) . . ?
C9 C8 C17 117.1(5) . . ?
C35 C10 C16 116.7(5) . . ?
N16 C11 C12 121.8(2) . . ?
N16 C11 N17 113.49(18) . . ?
N17 C11 C12 124.68(19) . . ?
C13 C12 C11 119.2(2) . . ?
C12 C13 C14 118.4(2) . . ?
C13 C14 N22 119.8(2) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 N22 120.1(2) . . ?
N16 C15 C14 121.8(2) . . ?
C15 N16 C11 118.64(19) . . ?
C8 C17 C20 119.5(4) . . ?
C11 N17 C18 128.5(2) . . ?
N17 C18 C19 113.6(2) . . ?
O21 C18 N17 123.0(2) . . ?
O21 C18 C19 123.5(2) . . ?
C20 C19 C18 116.3(2) . . ?
C19 C20 C17 117.0(3) . . ?
O23 N22 C14 118.9(2) . . ?
O24 N22 C14 118.4(2) . . ?
O24 N22 O23 122.7(2) . . ?
C26 C25 N31 124.0(2) . . ?
N30 C25 C26 123.0(3) . . ?
N30 C25 N31 112.9(2) . . ?
C27 C26 C25 118.5(2) . . ?
C28 C27 C26 118.8(3) . . ?
C27 C28 C29 119.3(3) . . ?
C27 C28 N37 120.5(3) . . ?
C29 C28 N37 120.2(3) . . ?
N30 C29 C28 123.4(3) . . ?
C29 N30 C25 116.9(2) . . ?
C32 N31 C25 129.3(2) . . ?
N31 C32 C33 114.5(2) . . ?
O36 C32 N31 121.7(3) . . ?
O36 C32 C33 123.8(2) . . ?
C34 C33 C32 115.1(3) . . ?
C35 C34 C33 115.6(3) . . ?
C34 C35 C10 118.1(4) . . ?
O38 N37 C28 118.5(3) . . ?
O39 N37 C28 118.9(3) . . ?
O39 N37 O38 122.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9 N16 0.86(3) 1.89(4) 2.747(2) 172(3) . yes
N10 H10C O39 0.87(3) 2.61(4) 3.184(4) 125(3) 2_655 yes
N10 H10D N10 0.88(4) 2.44(4) 3.260(5) 154(3) 2_655 yes
C15 H15 N30 0.92(3) 2.72(3) 3.610(3) 165(2) . yes
N17 H17 O8 0.83(3) 2.00(3) 2.828(3) 175(2) . yes
N31 H31 O23 0.76(3) 2.38(3) 3.144(3) 175(3) . yes

_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 1.716
_oxdiff_exptl_absorpt_empirical_full_min 0.724
####################################################################### 
# 
# 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_795
_database_code_depnum_ccdc_archive 'CCDC 2518011'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-11-04
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 N3 O3, C9 H11 N O2'
_chemical_formula_sum            'C17 H20 N4 O5'
_chemical_formula_weight         360.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H20N4O5
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.8829(8)
_cell_length_b                   6.1032(2)
_cell_length_c                   23.3288(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.391(4)
_cell_angle_gamma                90
_cell_volume                     3484.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3176
_cell_measurement_temperature    295.0(4)
_cell_measurement_theta_max      73.0320
_cell_measurement_theta_min      3.5860
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method 'crystallized from dichloromethane'
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11779
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.128
_diffrn_reflns_theta_min         3.612
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00 -50.00   0.50   50.00    --  -91.75  68.00 154.00   50
  2  ω   -157.00-130.00   0.50   50.00    --  -91.75 -68.00  21.00   54
  3  ω    -51.00 -26.00   0.50   50.00    --  -91.75  45.00 -60.00   50
  4  ω    -49.00 -22.00   0.50   50.00    --  -91.75  45.00   0.00   54
  5  ω    -67.00  17.00   0.50   12.00    --  -47.73  68.00 154.00  168
  6  ω    -25.00  27.00   0.50   12.00    --  -47.73  19.00 -60.00  104
  7  ω   -118.00 -29.00   0.50   12.00    --  -47.73 -68.00  21.00  178
  8  ω     93.00 118.00   0.50   12.00    --   47.73  68.00 154.00   50
  9  ω      7.00  49.00   0.50   12.00    --   47.73 -68.00  21.00   84
 10  ω     42.00  70.00   0.50   12.00    --   47.73  68.00 154.00   56
 11  ω     94.00 178.00   0.50   50.00    --  113.25  68.00 154.00  168
 12  ω     42.00  67.00   0.50   50.00    --  113.25 -68.00  21.00   50
 13  ω     94.00 127.00   0.50   50.00    --  113.25  77.00  90.00   66
 14  ω    137.00 178.00   0.50   50.00    --  113.25  77.00  90.00   82
 15  ω    107.00 140.00   0.50   50.00    --  113.25  45.00-120.00   66
 16  ω     52.00  79.00   0.50   50.00    --  113.25 -94.00-120.00   54
 17  ω     42.00  69.00   0.50   50.00    --  113.25 -61.00-120.00   54
 18  ω     42.00  67.00   0.50   50.00    --  113.25 -61.00  60.00   50
 19  ω     49.00 105.00   0.50   50.00    --  113.25 -77.00  60.00  112
 20  ω     43.00  70.00   0.50   50.00    --  113.25 -61.00 150.00   54
 21  ω     42.00  67.00   0.50   50.00    --  113.25 -61.00 -90.00   50
 22  ω    104.00 139.00   0.50   50.00    --  113.25  45.00-150.00   70
 23  ω    104.00 157.00   0.50   50.00    --  113.25  45.00 -90.00  106
 24  ω    153.00 178.00   0.50   50.00    --  113.25  45.00-150.00   50
 25  ω     44.00  86.00   0.50   50.00    --  113.25 -94.00  60.00   84
 26  ω     50.00  77.00   0.50   50.00    --  113.25 -77.00 120.00   54
 27  ω     46.00 111.00   0.50   50.00    --  113.25-125.00  30.00  130
 28  ω     49.00 111.00   0.50   50.00    --  113.25-125.00-150.00  124
 29  ω    147.00 176.00   0.50   50.00    --  113.25  45.00-120.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0038099000
_diffrn_orient_matrix_UB_12      0.0061890000
_diffrn_orient_matrix_UB_13      0.0666470000
_diffrn_orient_matrix_UB_21      -0.0402496000
_diffrn_orient_matrix_UB_22      0.1938423000
_diffrn_orient_matrix_UB_23      -0.0064452000
_diffrn_orient_matrix_UB_31      -0.0482502000
_diffrn_orient_matrix_UB_32      -0.1614168000
_diffrn_orient_matrix_UB_33      -0.0051392000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2357
_reflns_number_total             3650
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.048
_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)+(0.1122P)²+1.2324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C16(H16), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41491(10) 0.5859(5) 0.50201(13) 0.0624(7) Uani 1 1 d . . . . .
N2 N 0.39162(9) 0.3914(4) 0.48730(11) 0.0658(6) Uani 1 1 d . . . . .
C3 C 0.40073(10) 0.2907(5) 0.43991(14) 0.0674(7) Uani 1 1 d . . . . .
H3 H 0.383910 0.156712 0.429672 0.081 Uiso 1 1 calc R U . . .
H22 H 0.3438(19) 0.259(8) 0.520(2) 0.135(16) Uiso 1 1 d . . . . .
C4 C 0.43470(10) 0.3794(5) 0.40507(13) 0.0659(7) Uani 1 1 d . . . . .
H10 H 0.3822(15) 0.600(6) 0.5713(16) 0.085(10) Uiso 1 1 d . . . . .
C5 C 0.45819(11) 0.5822(5) 0.41878(14) 0.0682(7) Uani 1 1 d . . . . .
H5 H 0.480034 0.646193 0.394991 0.082 Uiso 1 1 calc R U . . .
C6 C 0.44891(10) 0.6876(5) 0.46781(13) 0.0652(7) Uani 1 1 d . . . . .
H6 H 0.464696 0.823200 0.478305 0.078 Uiso 1 1 calc R U . . .
N7 N 0.44331(10) 0.2587(5) 0.35395(12) 0.0762(7) Uani 1 1 d . . . . .
O8 O 0.47124(10) 0.3440(4) 0.32201(12) 0.0953(7) Uani 1 1 d . . . . .
O9 O 0.42311(10) 0.0755(4) 0.34512(12) 0.0920(7) Uani 1 1 d . . . . .
N10 N 0.40332(10) 0.6698(4) 0.55333(12) 0.0689(6) Uani 1 1 d . . . . .
C11 C 0.42586(11) 0.8483(5) 0.58474(14) 0.0679(7) Uani 1 1 d . . . . .
O12 O 0.45824(9) 0.9701(4) 0.56718(10) 0.0813(6) Uani 1 1 d . . . . .
C13 C 0.40884(12) 0.8742(6) 0.64268(15) 0.0782(8) Uani 1 1 d . . . . .
H13A H 0.419724 0.744408 0.665901 0.094 Uiso 1 1 calc R U . . .
H13B H 0.369314 0.883941 0.636748 0.094 Uiso 1 1 calc R U . . .
C14 C 0.43295(15) 1.0731(7) 0.67621(19) 0.0969(11) Uani 1 1 d . . . . .
H14A H 0.419280 1.203277 0.655481 0.145 Uiso 1 1 calc R U . . .
H14B H 0.472035 1.069040 0.680434 0.145 Uiso 1 1 calc R U . . .
H14C H 0.422875 1.073488 0.714040 0.145 Uiso 1 1 calc R U . . .
C15 C 0.25965(10) 0.0847(4) 0.59691(12) 0.0579(6) Uani 1 1 d . . . . .
C16 C 0.23540(10) 0.1489(4) 0.64344(12) 0.0581(6) Uani 1 1 d . . . . .
H16 H 0.243970 0.284356 0.660981 0.070 Uiso 1 1 calc R U . . .
C17 C 0.19803(10) 0.0104(4) 0.66413(12) 0.0584(6) Uani 1 1 d . . . . .
C18 C 0.18593(10) -0.1903(4) 0.63543(13) 0.0625(7) Uani 1 1 d . . . . .
H18 H 0.160721 -0.284211 0.647504 0.075 Uiso 1 1 calc R U . . .
C19 C 0.21079(11) -0.2506(5) 0.58961(14) 0.0692(8) Uani 1 1 d . . . . .
H19 H 0.202434 -0.385060 0.571432 0.083 Uiso 1 1 calc R U . . .
C20 C 0.24776(11) -0.1142(5) 0.57052(14) 0.0701(7) Uani 1 1 d . . . . .
H20 H 0.264634 -0.156779 0.539828 0.084 Uiso 1 1 calc R U . . .
C21 C 0.30057(10) 0.2322(4) 0.57699(13) 0.0616(6) Uani 1 1 d . . . . .
O22 O 0.31759(10) 0.1568(4) 0.53057(10) 0.0853(7) Uani 1 1 d . . . . .
O23 O 0.31714(8) 0.4019(3) 0.60075(10) 0.0755(6) Uani 1 1 d . . . . .
N24 N 0.17351(11) 0.0684(4) 0.71044(12) 0.0752(7) Uani 1 1 d . . . . .
C25 C 0.19050(14) 0.2617(6) 0.74412(16) 0.0876(10) Uani 1 1 d . . . . .
H25A H 0.227310 0.242902 0.764551 0.131 Uiso 1 1 calc R U . . .
H25B H 0.166731 0.285314 0.771695 0.131 Uiso 1 1 calc R U . . .
H25C H 0.188811 0.385918 0.718616 0.131 Uiso 1 1 calc R U . . .
C26 C 0.14374(14) -0.0926(5) 0.73802(16) 0.0809(9) Uani 1 1 d . . . . .
H26A H 0.131341 -0.027107 0.770707 0.121 Uiso 1 1 calc R U . . .
H26B H 0.167299 -0.214023 0.751142 0.121 Uiso 1 1 calc R U . . .
H26C H 0.112857 -0.143432 0.710463 0.121 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
C1 N2 1.338(4) . ?
C1 C6 1.407(4) . ?
C1 N10 1.380(4) . ?
N2 C3 1.320(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.381(4) . ?
C4 N7 1.450(4) . ?
C5 C6 1.368(4) . ?
N7 O8 1.223(3) . ?
N7 O9 1.228(3) . ?
N10 C11 1.375(4) . ?
C11 O12 1.220(3) . ?
C11 C13 1.496(4) . ?
C13 C14 1.509(5) . ?
C15 C16 1.390(4) . ?
C15 C20 1.369(4) . ?
C15 C21 1.495(3) . ?
C16 C17 1.405(3) . ?
C17 C18 1.403(4) . ?
C17 N24 1.379(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.373(4) . ?
C21 O22 1.315(3) . ?
C21 O23 1.211(3) . ?
N24 C25 1.438(4) . ?
N24 C26 1.449(4) . ?

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
N2 C1 C6 121.5(3) . . ?
N2 C1 N10 113.8(2) . . ?
N10 C1 C6 124.7(3) . . ?
C3 N2 C1 119.7(2) . . ?
N2 C3 C4 121.7(3) . . ?
C3 C4 N7 118.7(3) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 N7 121.8(3) . . ?
C6 C5 C4 119.1(3) . . ?
C5 C6 C1 118.4(3) . . ?
O8 N7 C4 118.0(3) . . ?
O8 N7 O9 123.1(3) . . ?
O9 N7 C4 118.9(3) . . ?
C11 N10 C1 128.9(2) . . ?
N10 C11 C13 114.2(2) . . ?
O12 C11 N10 122.3(3) . . ?
O12 C11 C13 123.4(3) . . ?
C11 C13 C14 113.7(3) . . ?
C16 C15 C21 119.3(2) . . ?
C20 C15 C16 120.8(2) . . ?
C20 C15 C21 119.9(2) . . ?
C15 C16 C17 120.4(2) . . ?
C18 C17 C16 117.4(2) . . ?
N24 C17 C16 121.9(2) . . ?
N24 C17 C18 120.7(2) . . ?
C19 C18 C17 121.0(2) . . ?
C20 C19 C18 120.7(3) . . ?
C15 C20 C19 119.6(3) . . ?
O22 C21 C15 112.6(2) . . ?
O23 C21 C15 124.6(3) . . ?
O23 C21 O22 122.8(2) . . ?
C17 N24 C25 120.7(2) . . ?
C17 N24 C26 120.5(2) . . ?
C25 N24 C26 115.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O22 H22 N2 0.96(5) 1.73(5) 2.671(3) 164(4) . yes
N10 H10 O23 0.84(4) 2.23(4) 3.058(3) 168(3) . yes

_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 1.558
_oxdiff_exptl_absorpt_empirical_full_min 0.564
####################################################################### 
# 
# 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_776_auto
_database_code_depnum_ccdc_archive 'CCDC 2518015'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-10-08
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N O2, C8 H9 N3 O3'
_chemical_formula_sum            'C15 H16 N4 O5'
_chemical_formula_weight         332.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15N4O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.5882(2)
_cell_length_b                   5.17490(7)
_cell_length_c                   23.3666(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.8814(16)
_cell_angle_gamma                90
_cell_volume                     1521.34(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5165
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      79.5320
_cell_measurement_theta_min      3.7810
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.772
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11401
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.786
_diffrn_reflns_theta_min         3.785
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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   -121.00 -51.00   0.50   12.00    --  -49.69  -9.00 -39.00  140
  2  ω    -25.00  19.00   0.50   12.00    --  -49.69   9.00 134.00   88
  3  ω    -11.00  25.00   0.50   12.00    --   49.69  -9.00 -39.00   72
  4  ω     65.00 117.00   0.50   12.00    --   49.69   9.00 134.00  104
  5  ω   -146.00-121.00   0.50   50.00    --  -90.00  -9.00 -39.00   50
  6  ω    103.00 177.00   0.50   50.00    --  111.50   9.00 134.00  148
  7  ω    -15.00  43.00   0.50   12.00    --   49.69 -38.00-150.00  116
  8  ω    -16.00  22.00   0.50   12.00    --   49.69 -19.00 120.00   76
  9  ω    -67.00 -41.00   0.50   50.00    --  -90.00  61.00-120.00   52
 10  ω    -51.00 -26.00   0.50   50.00    --  -90.00  45.00 120.00   50
 11  ω    -76.00 -51.00   0.50   50.00    --  -90.00 125.00-180.00   50
 12  ω    102.00 165.00   0.50   50.00    --  111.50  45.00-150.00  126
 13  ω    137.00 177.00   0.50   50.00    --  111.50  30.00   0.00   80
 14  ω     86.00 111.00   0.50   50.00    --  111.50-125.00 -60.00   50
 15  ω    104.00 129.00   0.50   50.00    --  111.50  30.00   0.00   50
 16  ω     46.00  71.00   0.50   50.00    --  111.50 -61.00 -90.00   50
 17  ω    127.00 172.00   0.50   50.00    --  111.50  30.00 -30.00   90
 18  ω     78.00 103.00   0.50   50.00    --  111.50 -94.00-150.00   50
 19  ω     43.00  78.00   0.50   50.00    --  111.50-125.00 -60.00   70
 20  ω    105.00 176.00   0.50   50.00    --  111.50  45.00  60.00  142
 21  ω     78.00 104.00   0.50   50.00    --  111.50 -94.00-180.00   52
 22  ω     83.00 110.00   0.50   50.00    --  111.50-125.00-150.00   54
 23  ω     60.00  85.00   0.50   50.00    --  111.50 -94.00 -90.00   50
 24  ω     51.00  91.00   0.50   50.00    --  111.50 -94.00-120.00   80
 25  ω     45.00  71.00   0.50   50.00    --  111.50-125.00-150.00   52
 26  ω     44.00  70.00   0.50   50.00    --  111.50 -61.00-180.00   52
 27  ω     46.00  71.00   0.50   50.00    --  111.50 -61.00  30.00   50
 28  ω     53.00  95.00   0.50   50.00    --  111.50 -94.00 150.00   84
 29  ω     45.00  70.00   0.50   50.00    --  111.50 -61.00 150.00   50
 30  ω     47.00  91.00   0.50   50.00    --  111.50 -77.00  90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0710108000
_diffrn_orient_matrix_UB_12      -0.0259153000
_diffrn_orient_matrix_UB_13      0.0521579000
_diffrn_orient_matrix_UB_21      0.0997044000
_diffrn_orient_matrix_UB_22      -0.0272216000
_diffrn_orient_matrix_UB_23      0.0395705000
_diffrn_orient_matrix_UB_31      0.0029803000
_diffrn_orient_matrix_UB_32      0.2952442000
_diffrn_orient_matrix_UB_33      0.0082093000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2645
_reflns_number_total             3225
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.084
_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)+(0.0352P)²+0.8380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
O8 O 0.32628(10) 0.6461(3) 0.61922(5) 0.0360(3) Uani 1 1 d . . . . .
O9 O 0.36174(11) 0.4880(3) 0.53298(5) 0.0414(3) Uani 1 1 d . . . . .
H9 H 0.312(2) 0.603(6) 0.5226(12) 0.070(8) Uiso 1 1 d . . . . .
O21 O 0.07817(11) 1.3816(3) 0.59551(6) 0.0411(3) Uani 1 1 d . . . . .
O23 O 0.17420(12) 0.7000(3) 0.32019(6) 0.0447(4) Uani 1 1 d . . . . .
O24 O 0.06765(11) 1.0267(3) 0.31006(6) 0.0426(3) Uani 1 1 d . . . . .
N10 N 0.67592(13) -0.2190(3) 0.68081(8) 0.0368(4) Uani 1 1 d . . . . .
H10A H 0.6762(18) -0.240(5) 0.7198(11) 0.051(7) Uiso 1 1 d . . . . .
H10B H 0.682(2) -0.377(6) 0.6625(12) 0.066(8) Uiso 1 1 d . . . . .
N16 N 0.21766(11) 0.8286(3) 0.48984(6) 0.0308(3) Uani 1 1 d . . . . .
N17 N 0.18365(12) 1.0408(3) 0.57246(6) 0.0309(3) Uani 1 1 d . . . . .
H17 H 0.2257(18) 0.923(5) 0.5863(10) 0.046(6) Uiso 1 1 d . . . . .
N22 N 0.12679(12) 0.8877(3) 0.33919(6) 0.0332(3) Uani 1 1 d . . . . .
C1 C 0.45383(13) 0.3091(3) 0.61262(7) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.49827(14) 0.1215(4) 0.57792(7) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.478825 0.116076 0.538312 0.039 Uiso 1 1 calc R U . . .
C3 C 0.56998(14) -0.0565(4) 0.60013(8) 0.0335(4) Uani 1 1 d . . . . .
H3 H 0.598908 -0.183837 0.575846 0.040 Uiso 1 1 calc R U . . .
C4 C 0.60029(13) -0.0504(3) 0.65811(7) 0.0277(3) Uani 1 1 d . . . . .
C5 C 0.55701(14) 0.1404(4) 0.69292(7) 0.0311(4) Uani 1 1 d . . . . .
H5 H 0.578026 0.149503 0.732292 0.037 Uiso 1 1 calc R U . . .
C6 C 0.48416(14) 0.3149(3) 0.67049(7) 0.0306(4) Uani 1 1 d . . . . .
H6 H 0.454269 0.440820 0.694797 0.037 Uiso 1 1 calc R U . . .
C7 C 0.37548(13) 0.4971(3) 0.58960(7) 0.0291(4) Uani 1 1 d . . . . .
C11 C 0.16662(13) 1.0269(3) 0.51413(7) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.10273(14) 1.1975(3) 0.48139(8) 0.0320(4) Uani 1 1 d . . . . .
H12 H 0.069136 1.339957 0.498987 0.038 Uiso 1 1 calc R U . . .
C13 C 0.08949(14) 1.1556(3) 0.42354(8) 0.0319(4) Uani 1 1 d . . . . .
H13 H 0.046161 1.266908 0.400401 0.038 Uiso 1 1 calc R U . . .
C14 C 0.14090(13) 0.9469(3) 0.39984(7) 0.0288(4) Uani 1 1 d . . . . .
C15 C 0.20488(14) 0.7902(3) 0.43373(8) 0.0310(4) Uani 1 1 d . . . . .
H15 H 0.241004 0.650444 0.416582 0.037 Uiso 1 1 calc R U . . .
C18 C 0.14019(13) 1.2121(3) 0.61053(8) 0.0302(4) Uani 1 1 d . . . . .
C19 C 0.17514(14) 1.1638(4) 0.67172(8) 0.0337(4) Uani 1 1 d . . . . .
H19A H 0.253514 1.146946 0.673847 0.040 Uiso 1 1 calc R U . . .
H19B H 0.144677 0.997648 0.684294 0.040 Uiso 1 1 calc R U . . .
C20 C 0.14261(18) 1.3737(4) 0.71240(9) 0.0451(5) Uani 1 1 d . . . . .
H20A H 0.180796 1.533403 0.703836 0.068 Uiso 1 1 calc R U . . .
H20B H 0.159985 1.320459 0.751852 0.068 Uiso 1 1 calc R U . . .
H20C H 0.065908 1.403591 0.707929 0.068 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
O8 C7 1.219(2) . ?
O9 C7 1.329(2) . ?
O21 C18 1.218(2) . ?
O23 N22 1.231(2) . ?
O24 N22 1.2253(19) . ?
N10 C4 1.384(2) . ?
N16 C11 1.346(2) . ?
N16 C15 1.331(2) . ?
N17 C11 1.375(2) . ?
N17 C18 1.381(2) . ?
N22 C14 1.455(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.393(2) . ?
C1 C7 1.474(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.396(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.379(2) . ?
C11 C12 1.404(2) . ?
C12 C13 1.374(3) . ?
C13 C14 1.384(3) . ?
C14 C15 1.375(2) . ?
C18 C19 1.503(2) . ?
C19 C20 1.509(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N16 C11 119.05(15) . . ?
C11 N17 C18 128.32(15) . . ?
O23 N22 C14 118.19(14) . . ?
O24 N22 O23 123.78(16) . . ?
O24 N22 C14 118.03(15) . . ?
C2 C1 C7 121.60(15) . . ?
C6 C1 C2 118.50(15) . . ?
C6 C1 C7 119.90(15) . . ?
C3 C2 C1 121.11(16) . . ?
C2 C3 C4 120.33(16) . . ?
N10 C4 C3 121.36(16) . . ?
N10 C4 C5 119.83(16) . . ?
C3 C4 C5 118.71(15) . . ?
C6 C5 C4 120.51(16) . . ?
C5 C6 C1 120.83(16) . . ?
O8 C7 O9 122.38(15) . . ?
O8 C7 C1 123.83(15) . . ?
O9 C7 C1 113.78(14) . . ?
N16 C11 N17 113.40(14) . . ?
N16 C11 C12 121.49(16) . . ?
N17 C11 C12 125.10(16) . . ?
C13 C12 C11 119.04(16) . . ?
C12 C13 C14 118.29(16) . . ?
C13 C14 N22 120.68(15) . . ?
C15 C14 N22 119.16(16) . . ?
C15 C14 C13 120.15(16) . . ?
N16 C15 C14 121.93(16) . . ?
O21 C18 N17 122.69(17) . . ?
O21 C18 C19 123.95(16) . . ?
N17 C18 C19 113.35(15) . . ?
C18 C19 C20 113.74(16) . . ?

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
O9 H9 N16 0.89(3) 1.82(3) 2.7005(19) 171(3) . yes
N10 H10A O23 0.92(3) 2.36(3) 3.259(2) 168(2) 4_666 yes
N10 H10B O23 0.92(3) 2.49(3) 3.124(2) 126(2) 3_656 yes
N17 H17 O8 0.86(2) 2.05(2) 2.9087(19) 180(2) . yes

_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 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.499
####################################################################### 
# 
# 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_781_auto
_database_code_depnum_ccdc_archive 'CCDC 2518014'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-10-12
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O2, C11 H15 N3 O3'
_chemical_formula_sum            'C20 H26 N4 O5'
_chemical_formula_weight         402.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C7H5O4N2
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                   6.42159(9)
_cell_length_b                   12.65205(14)
_cell_length_c                   13.02701(17)
_cell_angle_alpha                76.6124(10)
_cell_angle_beta                 75.8298(12)
_cell_angle_gamma                80.7872(10)
_cell_volume                     992.29(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15178
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      79.5850
_cell_measurement_theta_min      3.5690
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.037
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20759
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.934
_diffrn_reflns_theta_min         3.572
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -10.00   0.50    0.80    --  -49.82 121.00-134.00  148
  2  ω   -105.00 -27.00   0.50    0.80    --  -49.82 152.00  25.00  156
  3  ω   -121.00 -55.00   0.50    0.80    --  -49.82-152.00 -16.00  132
  4  ω     32.00  91.00   0.50    0.80    --   49.82-121.00 143.00  118
  5  ω     48.00 112.00   0.50    0.80    --   49.82-152.00 -16.00  128
  6  ω    -84.00 -21.00   0.50    3.50    --  -90.00 121.00-134.00  126
  7  ω   -105.00 -27.00   0.50    3.50    --  -90.00 152.00  25.00  156
  8  ω   -159.00 -76.00   0.50    3.50    --  -90.00-121.00 143.00  166
  9  ω   -148.00 -55.00   0.50    3.50    --  -90.00-152.00 -16.00  186
 10  ω     77.00 164.00   0.50    3.50    --  111.50 152.00  25.00  174
 11  ω     98.00 178.00   0.50    3.50    --  111.50 121.00-134.00  160
 12  ω    100.00 131.00   0.50    3.50    --  111.50-152.00 -16.00   62
 13  ω     52.00  77.00   0.50    3.50    --  111.50-121.00 143.00   50
 14  ω   -117.00 -77.00   0.50    0.80    --  -49.82-125.00-150.00   80
 15  ω    -24.00  23.00   0.50    0.80    --  -49.82  19.00-120.00   94
 16  ω    -23.00  16.00   0.50    0.80    --  -49.82  19.00 150.00   78
 17  ω   -119.00 -31.00   0.50    0.80    --  -49.82 -77.00-180.00  176
 18  ω    -40.00  21.00   0.50    0.80    --  -49.82  38.00 120.00  122
 19  ω   -160.00 -86.00   0.50    3.50    --  -90.00 -45.00-150.00  148
 20  ω    150.00 178.00   0.50    3.50    --  111.50  45.00-150.00   56
 21  ω    107.00 136.00   0.50    3.50    --  111.50  45.00-150.00   58
 22  ω    104.00 130.00   0.50    3.50    --  111.50  30.00 -30.00   52
 23  ω    130.00 169.00   0.50    3.50    --  111.50  15.00 150.00   78
 24  ω     44.00  69.00   0.50    3.50    --  111.50-125.00  60.00   50
 25  ω     85.00 110.00   0.50    3.50    --  111.50-125.00  60.00   50
 26  ω     92.00 117.00   0.50    3.50    --  111.50  77.00  30.00   50
 27  ω    153.00 178.00   0.50    3.50    --  111.50  77.00  30.00   50
 28  ω     48.00  82.00   0.50    3.50    --  111.50 -77.00-150.00   68
 29  ω     79.00 108.00   0.50    3.50    --  111.50-108.00  -6.10   58
 30  ω     79.00 111.00   0.50    3.50    --  111.50-125.00-150.00   64
 31  ω     53.00  78.00   0.50    3.50    --  111.50-125.00-150.00   50
 32  ω     49.00  97.00   0.50    3.50    --  111.50 -94.00  90.00   96
 33  ω     43.00  77.00   0.50    3.50    --  111.50-125.00   0.00   68
 34  ω     49.00  96.00   0.50    3.50    --  111.50 -77.00   0.00   94
 35  ω    118.00 173.00   0.50    3.50    --  111.50  15.00-150.00  110
 36  ω    102.00 155.00   0.50    3.50    --  111.50  45.00 -60.00  106
 37  ω    118.00 178.00   0.50    3.50    --  111.50  45.00-120.00  120
 38  ω     80.00 111.00   0.50    3.50    --  111.50-125.00-120.00   62
 39  ω     71.00 107.00   0.50    3.50    --  111.50-103.00 119.42   72
 40  ω     47.00  77.00   0.50    3.50    --  111.50 -82.00  -6.77   60
 41  ω     94.00 120.00   0.50    3.50    --  111.50 -82.00  -6.77   52
 42  ω    131.00 172.00   0.50    3.50    --  111.50  45.00 150.00   82
 43  ω     80.00 105.00   0.50    3.50    --  111.50 -77.00 120.00   50
 44  ω    107.00 163.00   0.50    3.50    --  111.50  30.00  90.00  112
 45  ω     43.00  70.00   0.50    3.50    --  111.50-125.00  90.00   54
 46  ω     43.00 102.00   0.50    3.50    --  111.50-125.00 -90.00  118
 47  ω     78.00 110.00   0.50    3.50    --  111.50-125.00 120.00   64
 48  ω     65.00 105.00   0.50    3.50    --  111.50 -94.00 -30.00   80
 49  ω    125.00 157.00   0.50    3.50    --  111.50  30.00-150.00   64
 50  ω     53.00  96.00   0.50    3.50    --  111.50 -77.00 150.00   86
 51  ω     51.00 103.00   0.50    3.50    --  111.50 -94.00 -60.00  104
 52  ω     41.00  76.00   0.50    3.50    --  111.50 -77.00 120.00   70
 53  ω     42.00  68.00   0.50    3.50    --  111.50 -94.00 120.00   52
 54  ω     78.00 104.00   0.50    3.50    --  111.50 -94.00 120.00   52
 55  ω     73.00 110.00   0.50    3.50    --  111.50-121.00 126.06   74
 56  ω    113.00 142.00   0.50    3.50    --  111.50  30.00 120.00   58
 57  ω    145.00 170.00   0.50    3.50    --  111.50  30.00 120.00   50
 58  ω    136.00 174.00   0.50    3.50    --  111.50  30.00 -30.00   76
 59  ω    101.00 139.00   0.50    3.50    --  111.50  61.00 150.00   76
 60  ω     43.00  87.00   0.50    3.50    --  111.50 -77.00-180.00   88
 61  ω     51.00  77.00   0.50    3.50    --  111.50 -77.00 -60.00   52
 62  ω     43.00  92.00   0.50    3.50    --  111.50 -77.00  30.00   98
 63  ω     44.00 104.00   0.50    3.50    --  111.50 -94.00 -90.00  120
 64  ω     42.00  68.00   0.50    3.50    --  111.50 -94.00 150.00   52
 65  ω     72.00  98.00   0.50    3.50    --  111.50 -94.00 150.00   52
 66  ω     70.00  95.00   0.50    3.50    --  111.50-125.00 -60.00   50
 67  ω    118.00 157.00   0.50    3.50    --  111.50  30.00  30.00   78
 68  ω    108.00 134.00   0.50    3.50    --  111.50  61.00 -30.00   52
 69  ω    124.00 174.00   0.50    3.50    --  111.50 125.00   0.00  100
 70  ω     93.00 138.00   0.50    3.50    --  111.50  77.00 -30.00   90
 71  ω     99.00 133.00   0.50    3.50    --  111.50 -82.00-177.03   68
 72  ω     88.00 114.00   0.50    3.50    --  111.50 -88.00 -19.07   52
 73  ω     42.00  68.00   0.50    3.50    --  111.50 -61.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0799782000
_diffrn_orient_matrix_UB_12      0.0133570000
_diffrn_orient_matrix_UB_13      -0.1233754000
_diffrn_orient_matrix_UB_21      -0.2261185000
_diffrn_orient_matrix_UB_22      -0.0166097000
_diffrn_orient_matrix_UB_23      -0.0100313000
_diffrn_orient_matrix_UB_31      -0.0665760000
_diffrn_orient_matrix_UB_32      0.1241135000
_diffrn_orient_matrix_UB_33      -0.0134522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3980
_reflns_number_total             4253
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.081
_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)+(0.0655P)²+0.1845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1156
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C14(H14), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.27478(17) 0.43907(8) 0.67135(8) 0.0299(2) Uani 1 1 d . . . . .
C2 C 0.09989(19) 0.43154(9) 0.62953(9) 0.0364(3) Uani 1 1 d . . . . .
H2 H 0.054227 0.489100 0.575793 0.044 Uiso 1 1 calc R U . . .
C3 C -0.00693(19) 0.33878(10) 0.66741(10) 0.0383(3) Uani 1 1 d . . . . .
H3 H -0.126459 0.332784 0.639002 0.046 Uiso 1 1 calc R U . . .
C4 C 0.05741(18) 0.25480(9) 0.74582(10) 0.0350(2) Uani 1 1 d . . . . .
H4 H -0.017613 0.191633 0.770112 0.042 Uiso 1 1 calc R U . . .
C5 C 0.23247(17) 0.26151(8) 0.79020(9) 0.0314(2) Uani 1 1 d . . . . .
C6 C 0.34050(17) 0.35580(8) 0.75133(8) 0.0302(2) Uani 1 1 d . . . . .
H6 H 0.459254 0.362776 0.779833 0.036 Uiso 1 1 calc R U . . .
C7 C 0.39233(18) 0.53848(9) 0.63272(9) 0.0316(2) Uani 1 1 d . . . . .
C11 C 0.1520(2) 0.09528(11) 0.92570(13) 0.0526(3) Uani 1 1 d . . . . .
H11A H 0.013778 0.131908 0.958621 0.079 Uiso 1 1 calc R U . . .
H11B H 0.214956 0.044771 0.982294 0.079 Uiso 1 1 calc R U . . .
H11C H 0.128255 0.054446 0.874936 0.079 Uiso 1 1 calc R U . . .
C12 C 0.4505(2) 0.19467(11) 0.92650(11) 0.0474(3) Uani 1 1 d . . . . .
H12A H 0.585123 0.213844 0.875342 0.071 Uiso 1 1 calc R U . . .
H12B H 0.480646 0.128008 0.978896 0.071 Uiso 1 1 calc R U . . .
H12C H 0.388648 0.254582 0.964620 0.071 Uiso 1 1 calc R U . . .
C13 C 0.66804(18) 0.83023(8) 0.50132(9) 0.0308(2) Uani 1 1 d . . . . .
C14 C 0.75495(19) 0.92662(9) 0.44092(9) 0.0345(2) Uani 1 1 d . . . . .
H14 H 0.873051 0.950475 0.457973 0.041 Uiso 1 1 calc R U . . .
C15 C 0.66489(19) 0.98556(9) 0.35654(9) 0.0358(2) Uani 1 1 d . . . . .
H15 H 0.719250 1.051262 0.314323 0.043 Uiso 1 1 calc R U . . .
C16 C 0.49323(19) 0.94739(9) 0.33416(9) 0.0343(2) Uani 1 1 d . . . . .
C17 C 0.41714(19) 0.85154(9) 0.39601(9) 0.0345(2) Uani 1 1 d . . . . .
H17 H 0.300277 0.825845 0.379683 0.041 Uiso 1 1 calc R U . . .
C20 C 0.88427(18) 0.78583(9) 0.64251(9) 0.0346(2) Uani 1 1 d . . . . .
C21 C 0.90501(19) 0.70300(9) 0.74438(10) 0.0366(3) Uani 1 1 d . . . . .
H21A H 0.945617 0.629477 0.726552 0.044 Uiso 1 1 calc R U . . .
H21B H 0.762830 0.702410 0.795572 0.044 Uiso 1 1 calc R U . . .
C22 C 1.07215(19) 0.72605(10) 0.79927(10) 0.0381(3) Uani 1 1 d . . . . .
H22A H 1.214346 0.727279 0.748095 0.046 Uiso 1 1 calc R U . . .
H22B H 1.030856 0.799079 0.818206 0.046 Uiso 1 1 calc R U . . .
C23 C 1.0920(2) 0.64075(10) 0.90110(10) 0.0388(3) Uani 1 1 d . . . . .
H23A H 0.951108 0.642381 0.953257 0.047 Uiso 1 1 calc R U . . .
H23B H 1.124533 0.567496 0.882365 0.047 Uiso 1 1 calc R U . . .
C24 C 1.2650(2) 0.65703(11) 0.95535(12) 0.0469(3) Uani 1 1 d . . . . .
H24A H 1.238670 0.731934 0.970041 0.056 Uiso 1 1 calc R U . . .
H24B H 1.407874 0.649779 0.905586 0.056 Uiso 1 1 calc R U . . .
C25 C 1.2688(2) 0.57498(12) 1.06072(12) 0.0499(3) Uani 1 1 d . . . . .
H25A H 1.288724 0.500635 1.047081 0.075 Uiso 1 1 calc R U . . .
H25B H 1.131819 0.585917 1.112414 0.075 Uiso 1 1 calc R U . . .
H25C H 1.388248 0.585495 1.090582 0.075 Uiso 1 1 calc R U . . .
N10 N 0.29855(17) 0.17629(8) 0.86835(9) 0.0412(2) Uani 1 1 d . . . . .
N18 N 0.50307(15) 0.79400(7) 0.47805(8) 0.0325(2) Uani 1 1 d . . . . .
N19 N 0.73944(16) 0.76411(8) 0.58961(8) 0.0346(2) Uani 1 1 d . . . . .
H19 H 0.682(3) 0.7038(14) 0.6151(13) 0.046(4) Uiso 1 1 d . . . . .
N27 N 0.39284(18) 1.00624(8) 0.24535(8) 0.0410(2) Uani 1 1 d . . . . .
O8 O 0.53718(14) 0.55468(7) 0.67043(7) 0.0413(2) Uani 1 1 d . . . . .
O9 O 0.31944(15) 0.60893(7) 0.55378(7) 0.0431(2) Uani 1 1 d . . . . .
H9 H 0.392(3) 0.6680(17) 0.5360(17) 0.073(6) Uiso 1 1 d . . . . .
O26 O 0.98271(16) 0.86582(7) 0.61075(8) 0.0486(2) Uani 1 1 d . . . . .
O28 O 0.24312(17) 0.96890(8) 0.22802(8) 0.0521(3) Uani 1 1 d . . . . .
O29 O 0.46343(18) 1.09117(8) 0.19181(8) 0.0555(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3874(15) . ?
C1 C6 1.3923(14) . ?
C1 C7 1.4933(14) . ?
C2 C3 1.3840(16) . ?
C3 C4 1.3808(17) . ?
C4 C5 1.4059(16) . ?
C5 C6 1.4050(14) . ?
C5 N10 1.3913(14) . ?
C7 O8 1.2165(13) . ?
C7 O9 1.3224(13) . ?
C11 N10 1.4506(16) . ?
C12 N10 1.4479(17) . ?
C13 C14 1.4058(14) . ?
C13 N18 1.3421(14) . ?
C13 N19 1.3867(14) . ?
C14 C15 1.3756(16) . ?
C15 C16 1.3880(16) . ?
C16 C17 1.3795(15) . ?
C16 N27 1.4564(15) . ?
C17 N18 1.3329(15) . ?
C20 C21 1.5083(16) . ?
C20 N19 1.3779(14) . ?
C20 O26 1.2157(14) . ?
C21 C22 1.5233(16) . ?
C22 C23 1.5220(16) . ?
C23 C24 1.5168(16) . ?
C24 C25 1.5201(19) . ?
N27 O28 1.2245(14) . ?
N27 O29 1.2251(14) . ?

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
C2 C1 C6 120.86(10) . . ?
C2 C1 C7 120.17(10) . . ?
C6 C1 C7 118.95(9) . . ?
C3 C2 C1 118.90(10) . . ?
C4 C3 C2 121.06(10) . . ?
C3 C4 C5 120.89(10) . . ?
C6 C5 C4 117.80(10) . . ?
N10 C5 C4 120.80(10) . . ?
N10 C5 C6 121.39(10) . . ?
C1 C6 C5 120.48(10) . . ?
O8 C7 C1 124.17(10) . . ?
O8 C7 O9 123.10(10) . . ?
O9 C7 C1 112.72(9) . . ?
N18 C13 C14 121.97(10) . . ?
N18 C13 N19 113.37(9) . . ?
N19 C13 C14 124.65(10) . . ?
C15 C14 C13 118.42(10) . . ?
C14 C15 C16 118.85(10) . . ?
C15 C16 N27 121.10(10) . . ?
C17 C16 C15 119.76(10) . . ?
C17 C16 N27 119.14(10) . . ?
N18 C17 C16 121.82(10) . . ?
N19 C20 C21 113.90(9) . . ?
O26 C20 C21 123.29(10) . . ?
O26 C20 N19 122.79(11) . . ?
C20 C21 C22 113.07(9) . . ?
C23 C22 C21 112.12(9) . . ?
C24 C23 C22 113.99(10) . . ?
C23 C24 C25 112.24(11) . . ?
C5 N10 C11 118.86(10) . . ?
C5 N10 C12 118.77(10) . . ?
C12 N10 C11 116.02(11) . . ?
C17 N18 C13 119.18(9) . . ?
C20 N19 C13 127.52(9) . . ?
O28 N27 C16 118.79(10) . . ?
O28 N27 O29 123.43(11) . . ?
O29 N27 C16 117.78(11) . . ?

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
N19 H19 O8 0.861(17) 2.133(18) 2.9928(12) 177.1(15) . yes
O9 H9 N18 0.90(2) 1.78(2) 2.6630(12) 167(2) . yes

_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.790
####################################################################### 
# 
# 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_787_auto
_database_code_depnum_ccdc_archive 'CCDC 2518017'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-10-26
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H7 N O2, C10 H13 N3 O3'
_chemical_formula_sum            'C17 H20 N4 O5'
_chemical_formula_weight         360.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H20N4O5
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                   6.15171(12)
_cell_length_b                   12.3495(4)
_cell_length_c                   12.6749(4)
_cell_angle_alpha                73.875(3)
_cell_angle_beta                 79.965(2)
_cell_angle_gamma                76.405(2)
_cell_volume                     892.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8885
_cell_measurement_temperature    295.9(3)
_cell_measurement_theta_max      79.5070
_cell_measurement_theta_min      3.6520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14844
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.078
_diffrn_reflns_theta_min         3.655
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  25.00   0.50    3.00    --  -47.98  33.00  52.00  126
  2  ω    -85.00 -36.00   0.50    3.00    --  -47.98 -33.00-105.00   98
  3  ω   -118.00 -88.00   0.50    3.00    --  -47.98 -33.00-105.00   60
  4  ω    -71.00 -24.00   0.50    3.00    --  -47.98  77.00-120.00   94
  5  ω    -20.00  28.00   0.50    3.00    --  -47.98  19.00 -30.00   96
  6  ω     -5.00  20.00   0.50    3.00    --  -47.98  77.00-120.00   50
  7  ω    -26.00  10.00   0.50    3.00    --   47.98 -19.00 120.00   72
  8  ω     51.00 116.00   0.50    3.00    --   47.98  33.00  52.00  130
  9  ω    -23.00  37.00   0.50    3.00    --   47.98 -33.00-105.00  120
 10  ω     37.00  93.00   0.50    3.00    --   47.98-125.00   0.00  112
 11  ω   -130.00 -95.00   0.50   12.00    --  -91.75 -33.00-105.00   70
 12  ω    -76.00 -29.00   0.50   12.00    --  -91.75 125.00  90.00   94
 13  ω    139.00 170.00   0.50   12.00    --  113.25  33.00  52.00   62
 14  ω    103.00 129.00   0.50   12.00    --  113.25  33.00  52.00   52
 15  ω     46.00 102.00   0.50   12.00    --  113.25 -94.00 -60.00  112
 16  ω    101.00 173.00   0.50   12.00    --  113.25  30.00-180.00  144
 17  ω    111.00 155.00   0.50   12.00    --  113.25   0.00-150.00   88
 18  ω     70.00  96.00   0.50   12.00    --  113.25 -94.00 120.00   52
 19  ω     85.00 111.00   0.50   12.00    --  113.25-125.00  30.00   52
 20  ω     79.00 104.00   0.50   12.00    --  113.25 -94.00 -90.00   50
 21  ω     45.00  70.00   0.50   12.00    --  113.25 -61.00 150.00   50
 22  ω     43.00  70.00   0.50   12.00    --  113.25 -61.00 -60.00   54
 23  ω     74.00 104.00   0.50   12.00    --  113.25 -77.00   0.00   60
 24  ω     42.00  71.00   0.50   12.00    --  113.25 -61.00-180.00   58
 25  ω     42.00  69.00   0.50   12.00    --  113.25 -61.00 -30.00   54
 26  ω     66.00 107.00   0.50   12.00    --  113.25-104.00 155.29   82
 27  ω     42.00  96.00   0.50   12.00    --  113.25 -77.00-120.00  108
 28  ω     45.00  74.00   0.50   12.00    --  113.25 -77.00-180.00   58
 29  ω     45.00  71.00   0.50   12.00    --  113.25 -77.00  30.00   52
 30  ω     72.00 109.00   0.50   12.00    --  113.25-125.00 150.00   74
 31  ω    109.00 177.00   0.50   12.00    --  113.25  30.00-120.00  136
 32  ω     78.00 111.00   0.50   12.00    --  113.25-125.00 -60.00   66
 33  ω     54.00 106.00   0.50   12.00    --  113.25 -94.00-180.00  104
 34  ω     42.00  76.00   0.50   12.00    --  113.25 -94.00 -90.00   68
 35  ω    124.00 150.00   0.50   12.00    --  113.25 125.00-150.00   52
 36  ω     70.00  96.00   0.50   12.00    --  113.25 -94.00-150.00   52
 37  ω     43.00  70.00   0.50   12.00    --  113.25 -77.00   0.00   54
 38  ω    142.00 176.00   0.50   12.00    --  113.25  30.00-150.00   68
 39  ω     79.00 104.00   0.50   12.00    --  113.25 -94.00  30.00   50
 40  ω     49.00  79.00   0.50   12.00    --  113.25 -77.00 -60.00   60
 41  ω    103.00 175.00   0.50   12.00    --  113.25  45.00 120.00  144
 42  ω    116.00 141.00   0.50   12.00    --  113.25  30.00-150.00   50
 43  ω     95.00 129.00   0.50   12.00    --  113.25 125.00 -90.00   68
 44  ω    133.00 164.00   0.50   12.00    --  113.25 125.00 -90.00   62
 45  ω    101.00 126.00   0.50   12.00    --  113.25  77.00 150.00   50
 46  ω     46.00  71.00   0.50   12.00    --  113.25 -94.00 150.00   50
 47  ω     78.00 105.00   0.50   12.00    --  113.25 -94.00 150.00   54
 48  ω     64.00  90.00   0.50   12.00    --  113.25 -86.00 -76.10   52
 49  ω     99.00 124.00   0.50   12.00    --  113.25 -86.00 -76.10   50
 50  ω    101.00 154.00   0.50   12.00    --  113.25  45.00 -60.00  106
 51  ω     46.00 111.00   0.50   12.00    --  113.25-125.00 120.00  130
 52  ω     79.00 104.00   0.50   12.00    --  113.25 -77.00-150.00   50
 53  ω    107.00 137.00   0.50   12.00    --  113.25 -79.00  58.70   60
 54  ω     81.00 106.00   0.50   12.00    --  113.25 -94.00 -30.00   50
 55  ω     52.00  78.00   0.50   12.00    --  113.25 -94.00   0.00   52
 56  ω     81.00 106.00   0.50   12.00    --  113.25 -94.00   0.00   50
 57  ω     72.00 106.00   0.50   12.00    --  113.25 -94.00  90.00   68
 58  ω     83.00 108.00   0.50   12.00    --  113.25-108.00 -83.67   50
 59  ω     44.00  74.00   0.50   12.00    --  113.25-125.00  90.00   60
 60  ω    131.00 157.00   0.50   12.00    --  113.25  45.00   0.00   52
 61  ω    113.00 173.00   0.50   12.00    --  113.25  30.00  90.00  120
 62  ω    115.00 140.00   0.50   12.00    --  113.25  30.00 120.00   50
 63  ω    120.00 159.00   0.50   12.00    --  113.25  61.00 -30.00   78
 64  ω    100.00 126.00   0.50   12.00    --  113.25  61.00  30.00   52
 65  ω     74.00 107.00   0.50   12.00    --  113.25-106.00  83.85   66
 66  ω    101.00 126.00   0.50   12.00    --  113.25  77.00  30.00   50
 67  ω    135.00 177.00   0.50   12.00    --  113.25  77.00  90.00   84
 68  ω     46.00  72.00   0.50   12.00    --  113.25 -79.00  58.70   52
 69  ω     42.00  68.00   0.50   12.00    --  113.25 -94.00  30.00   52
 70  ω     60.00 111.00   0.50   12.00    --  113.25-125.00 -90.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0680136000
_diffrn_orient_matrix_UB_12      -0.1305299000
_diffrn_orient_matrix_UB_13      0.0485166000
_diffrn_orient_matrix_UB_21      -0.2252990000
_diffrn_orient_matrix_UB_22      -0.0166714000
_diffrn_orient_matrix_UB_23      -0.0241017000
_diffrn_orient_matrix_UB_31      0.1091667000
_diffrn_orient_matrix_UB_32      -0.0152430000
_diffrn_orient_matrix_UB_33      -0.1152915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3482
_reflns_number_total             3854
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.079
_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)+(0.0744P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O25, N24
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C6(H6), C14(H14), C2(H2), C5(H5), C3(H3)
3.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O9 O 0.68667(16) 0.44053(8) 0.40944(7) 0.0633(2) Uani 1 1 d . . . . .
N11 N 0.51693(16) 0.54563(8) 0.20382(7) 0.0551(2) Uani 1 1 d . . . . .
C1 C 0.66171(18) 0.29337(9) 0.57405(8) 0.0512(2) Uani 1 1 d . . . . .
O8 O 0.41217(18) 0.34292(10) 0.43915(7) 0.0773(3) Uani 1 1 d . . . . .
N17 N 0.27778(18) 0.42332(9) 0.22745(8) 0.0593(3) Uani 1 1 d . . . . .
C15 C 0.5266(2) 0.70590(10) 0.05002(10) 0.0610(3) Uani 1 1 d . . . . .
C20 C -0.0728(2) 0.19917(11) 0.27934(10) 0.0604(3) Uani 1 1 d . . . . .
H20A H -0.034687 0.176820 0.209790 0.072 Uiso 1 1 calc R U . . .
H20B H -0.216259 0.252714 0.276662 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2713(2) 0.58526(11) 0.06331(9) 0.0610(3) Uani 1 1 d . . . . .
H13 H 0.159085 0.564981 0.036479 0.073 Uiso 1 1 calc R U . . .
C16 C 0.6017(2) 0.63745(11) 0.14762(10) 0.0597(3) Uani 1 1 d . . . . .
H16 H 0.715223 0.656010 0.175062 0.072 Uiso 1 1 calc R U . . .
C6 C 0.5581(2) 0.20303(10) 0.63663(9) 0.0577(3) Uani 1 1 d . . . . .
H6 H 0.435108 0.189695 0.612169 0.069 Uiso 1 1 calc R U . . .
O23 O 0.05550(19) 0.39085(9) 0.11784(8) 0.0804(3) Uani 1 1 d . . . . .
C14 C 0.3593(2) 0.68032(11) 0.00685(10) 0.0646(3) Uani 1 1 d . . . . .
H14 H 0.307507 0.726432 -0.058944 0.078 Uiso 1 1 calc R U . . .
C12 C 0.35459(19) 0.51949(9) 0.16238(8) 0.0526(2) Uani 1 1 d . . . . .
C18 C 0.1384(2) 0.36323(10) 0.20394(9) 0.0559(3) Uani 1 1 d . . . . .
C2 C 0.8450(2) 0.31216(11) 0.61200(10) 0.0579(3) Uani 1 1 d . . . . .
H2 H 0.916790 0.371828 0.571584 0.070 Uiso 1 1 calc R U . . .
O26 O 0.5545(3) 0.86525(11) -0.09316(11) 0.1080(4) Uani 1 1 d . . . . .
C5 C 0.6334(2) 0.13339(11) 0.73335(10) 0.0631(3) Uani 1 1 d . . . . .
H5 H 0.561319 0.073743 0.773548 0.076 Uiso 1 1 calc R U . . .
C7 C 0.57407(19) 0.36067(10) 0.46953(9) 0.0547(3) Uani 1 1 d . . . . .
O25 O 0.7665(3) 0.82859(12) 0.03499(11) 0.1032(4) Uani 1 1 d . U . . .
C4 C 0.8170(2) 0.15179(11) 0.77144(10) 0.0612(3) Uani 1 1 d . . . . .
C21 C -0.0940(2) 0.09355(11) 0.37344(12) 0.0679(3) Uani 1 1 d . . . . .
H21A H 0.048050 0.039007 0.373361 0.081 Uiso 1 1 calc R U . . .
H21B H -0.122456 0.115874 0.442934 0.081 Uiso 1 1 calc R U . . .
C3 C 0.9209(2) 0.24260(12) 0.70943(10) 0.0639(3) Uani 1 1 d . . . . .
H3 H 1.043146 0.256322 0.734256 0.077 Uiso 1 1 calc R U . . .
N24 N 0.6218(2) 0.80652(11) -0.00609(10) 0.0779(3) Uani 1 1 d . U . . .
N10 N 0.8892(3) 0.08185(14) 0.86942(11) 0.0856(4) Uani 1 1 d . . . . .
C19 C 0.1065(2) 0.25773(11) 0.29385(10) 0.0601(3) Uani 1 1 d . . . . .
H19A H 0.067465 0.278834 0.363988 0.072 Uiso 1 1 calc R U . . .
H19B H 0.248571 0.203078 0.297386 0.072 Uiso 1 1 calc R U . . .
C22 C -0.2785(3) 0.03510(16) 0.36698(18) 0.0949(5) Uani 1 1 d . . . . .
H22A H -0.261711 0.020612 0.295108 0.142 Uiso 1 1 calc R U . . .
H22B H -0.422188 0.083809 0.379367 0.142 Uiso 1 1 calc R U . . .
H22C H -0.269386 -0.036405 0.422356 0.142 Uiso 1 1 calc R U . . .
H17 H 0.328(3) 0.3989(14) 0.2911(14) 0.070(4) Uiso 1 1 d . . . . .
H9 H 0.631(3) 0.4712(16) 0.3481(15) 0.082(5) Uiso 1 1 d . . . . .
H10A H 0.839(5) 0.016(3) 0.900(2) 0.143(10) Uiso 1 1 d . . . . .
H10B H 1.009(4) 0.1033(18) 0.8784(17) 0.096(6) 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
O9 C7 1.3239(14) . ?
N11 C16 1.3287(15) . ?
N11 C12 1.3438(14) . ?
C1 C6 1.3951(16) . ?
C1 C2 1.3894(15) . ?
C1 C7 1.4708(15) . ?
O8 C7 1.2130(14) . ?
N17 C12 1.3777(15) . ?
N17 C18 1.3733(15) . ?
C15 C16 1.3760(17) . ?
C15 C14 1.3795(19) . ?
C15 N24 1.4487(17) . ?
C20 C21 1.5174(18) . ?
C20 C19 1.5143(16) . ?
C13 C14 1.3715(18) . ?
C13 C12 1.4005(15) . ?
C6 C5 1.3717(17) . ?
O23 C18 1.2135(14) . ?
C18 C19 1.5007(16) . ?
C2 C3 1.3800(17) . ?
O26 N24 1.2202(18) . ?
C5 C4 1.3904(18) . ?
O25 N24 1.2215(19) . ?
C4 C3 1.3986(19) . ?
C4 N10 1.3790(16) . ?
C21 C22 1.506(2) . ?

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
C16 N11 C12 118.21(10) . . ?
C6 C1 C7 117.62(10) . . ?
C2 C1 C6 118.39(10) . . ?
C2 C1 C7 123.95(10) . . ?
C18 N17 C12 129.06(9) . . ?
C16 C15 C14 120.43(11) . . ?
C16 C15 N24 119.38(12) . . ?
C14 C15 N24 120.18(12) . . ?
C19 C20 C21 111.18(10) . . ?
C14 C13 C12 118.31(11) . . ?
N11 C16 C15 121.93(11) . . ?
C5 C6 C1 121.61(11) . . ?
C13 C14 C15 118.40(11) . . ?
N11 C12 N17 113.42(9) . . ?
N11 C12 C13 122.71(10) . . ?
N17 C12 C13 123.86(10) . . ?
N17 C18 C19 112.99(9) . . ?
O23 C18 N17 123.33(11) . . ?
O23 C18 C19 123.64(11) . . ?
C3 C2 C1 120.25(11) . . ?
C6 C5 C4 120.15(12) . . ?
O9 C7 C1 115.51(10) . . ?
O8 C7 O9 122.08(10) . . ?
O8 C7 C1 122.40(11) . . ?
C5 C4 C3 118.55(11) . . ?
N10 C4 C5 119.49(13) . . ?
N10 C4 C3 121.96(13) . . ?
C22 C21 C20 113.71(13) . . ?
C2 C3 C4 121.05(11) . . ?
O26 N24 C15 118.27(14) . . ?
O26 N24 O25 122.80(13) . . ?
O25 N24 C15 118.92(13) . . ?
C18 C19 C20 114.57(10) . . ?

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
C13 H13 O23 0.93 2.30 2.8741(16) 119.7 . yes
C13 H13 O23 0.93 2.42 3.2176(14) 144.4 2_565 yes
N17 H17 O8 0.864(18) 1.927(18) 2.7887(13) 174.4(15) . yes
O9 H9 N11 0.86(2) 1.97(2) 2.8283(12) 177.2(17) . yes
N10 H10A O25 0.90(3) 2.55(3) 3.416(2) 162(2) 1_546 yes
N10 H10B O25 0.87(2) 2.33(2) 3.149(2) 157.2(17) 2_766 yes

_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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.735
####################################################################### 
# 
# 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_654
_database_code_depnum_ccdc_archive 'CCDC 2518016'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-02-05
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N3 O3, C7 H7 N O2'
_chemical_formula_sum            'C16 H18 N4 O5'
_chemical_formula_weight         346.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H18N4O5
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                   5.8059(4)
_cell_length_b                   11.8005(10)
_cell_length_c                   12.9057(16)
_cell_angle_alpha                73.991(9)
_cell_angle_beta                 78.882(9)
_cell_angle_gamma                78.277(7)
_cell_volume                     823.35(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6508
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      79.8590
_cell_measurement_theta_min      3.5960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 -1 0.0312
-1 -2 -2 0.0511
-2 1 0 0.0587
0 1 1 0.0589
2 4 1 0.0794
0 -4 1 0.0380
0 4 -1 0.0800
1 4 0 0.0621
1 -1 4 0.0580
0 1 -3 0.0724
-1 -1 4 0.0427
-4 -4 -1 0.0399

_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.107
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0007 -2.0025 -1.0014 -0.2903 0.1695 -0.2646
-0.9998 -1.9977 -2.0034 -0.1994 0.1491 0.2713
-2.0002 1.0081 -0.0250 0.2095 -0.1278 0.5313
0.0001 1.0024 0.9970 0.1181 -0.1099 -0.0048
2.0062 3.9920 1.0064 0.4548 0.0717 -0.5070
-0.0072 -3.9946 1.0165 -0.5646 -0.1771 -0.0412
0.0072 3.9946 -1.0165 0.5646 0.1771 0.0412
1.0067 3.9933 -0.0050 0.5097 0.1244 -0.2329
0.9941 -0.9916 4.0181 -0.2467 -0.4360 -0.3176
0.0054 0.9903 -3.0066 0.1918 0.3833 0.0435
-1.0076 -0.9829 3.9970 -0.1737 -0.5772 0.2064
-4.0079 -3.9833 -1.0275 -0.3818 -0.2129 1.0310

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11962
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         81.117
_diffrn_reflns_theta_min         3.601
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -21.00   0.50    0.80    --  -49.44 122.00 -58.00   60
  2  ω    -96.00 -59.00   0.50    0.80    --  -49.44-151.00  58.00   74
  3  ω    -74.00 -48.00   0.50    0.80    --  -49.44 151.00 102.00   52
  4  ω     53.00 111.00   0.50    0.80    --   49.44-151.00  58.00  116
  5  ω     51.00  90.00   0.50    0.80    --   49.44-122.00-140.00   78
  6  ω   -141.00-116.00   0.50    3.50    --  -90.00-122.00-140.00   50
  7  ω   -102.00 -77.00   0.50    3.50    --  -90.00-151.00  58.00   50
  8  ω    -77.00 -52.00   0.50    3.50    --  -90.00 122.00 -58.00   50
  9  ω    -89.00 -64.00   0.50    3.50    --  -90.00 151.00 102.00   50
 10  ω     63.00  90.00   0.50    3.50    --  111.50-151.00  58.00   54
 11  ω     53.00  80.00   0.50    3.50    --  111.50-122.00-140.00   54
 12  ω    113.00 138.00   0.50    3.50    --  111.50 122.00 -58.00   50
 13  ω    131.00 156.00   0.50    3.50    --  111.50 151.00 102.00   50
 14  ω   -112.00 -87.00   0.50    0.80    --  -49.44-125.00   0.00   50
 15  ω    -15.00  23.00   0.50    0.80    --  -49.44  19.00-120.00   76
 16  ω    -11.00  17.00   0.50    0.80    --  -49.44  19.00  60.00   56
 17  ω    -26.00  19.00   0.50    0.80    --  -49.44  19.00-150.00   90
 18  ω    -25.00   9.00   0.50    0.80    --  -49.44  19.00-180.00   68
 19  ω    -18.00  22.00   0.50    0.80    --   49.44 -19.00 150.00   80
 20  ω    -23.00  20.00   0.50    0.80    --   49.44 -19.00-150.00   86
 21  ω    -50.00 -22.00   0.50    3.50    --  -90.00  45.00   0.00   56
 22  ω    -50.00 -25.00   0.50    3.50    --  -90.00  45.00  90.00   50
 23  ω   -154.00 -82.00   0.50    3.50    --  -90.00 -30.00 -90.00  144
 24  ω     43.00  87.00   0.50    3.50    --  111.50 -94.00  60.00   88
 25  ω    104.00 166.00   0.50    3.50    --  111.50  30.00-180.00  124
 26  ω     47.00 110.00   0.50    3.50    --  111.50-125.00-180.00  126
 27  ω     42.00 104.00   0.50    3.50    --  111.50 -77.00   0.00  124
 28  ω     42.00  68.00   0.50    3.50    --  111.50 -61.00 -60.00   52
 29  ω    144.00 177.00   0.50    3.50    --  111.50  15.00 -60.00   66
 30  ω    114.00 169.00   0.50    3.50    --  111.50  15.00 120.00  110
 31  ω    103.00 166.00   0.50    3.50    --  111.50  45.00 -30.00  126
 32  ω     44.00 104.00   0.50    3.50    --  111.50 -94.00-120.00  120
 33  ω     43.00  71.00   0.50    3.50    --  111.50 -61.00-180.00   56
 34  ω     70.00 107.00   0.50    3.50    --  111.50-104.00-150.84   74
 35  ω    105.00 135.00   0.50    3.50    --  111.50  15.00 -60.00   60
 36  ω     46.00  93.00   0.50    3.50    --  111.50 -77.00-120.00   94
 37  ω    141.00 166.00   0.50    3.50    --  111.50  30.00   0.00   50
 38  ω    103.00 159.00   0.50    3.50    --  111.50  45.00  30.00  112
 39  ω     73.00 100.00   0.50    3.50    --  111.50 -94.00  90.00   54
 40  ω     44.00  71.00   0.50    3.50    --  111.50-125.00  30.00   54
 41  ω     85.00 110.00   0.50    3.50    --  111.50-125.00  30.00   50
 42  ω     48.00 101.00   0.50    3.50    --  111.50 -94.00 -60.00  106
 43  ω    117.00 155.00   0.50    3.50    --  111.50  15.00 -90.00   76
 44  ω     41.00 102.00   0.50    3.50    --  111.50 -77.00  60.00  122
 45  ω     50.00 105.00   0.50    3.50    --  111.50 -94.00-180.00  110
 46  ω    103.00 176.00   0.50    3.50    --  111.50  45.00-150.00  146
 47  ω     42.00  67.00   0.50    3.50    --  111.50 -61.00  90.00   50
 48  ω     44.00  69.00   0.50    3.50    --  111.50 -61.00-120.00   50
 49  ω     44.00  69.00   0.50    3.50    --  111.50 -61.00  60.00   50
 50  ω    104.00 143.00   0.50    3.50    --  111.50 151.00 103.00   78
 51  ω     57.00 107.00   0.50    3.50    --  111.50-103.00-175.47  100
 52  ω    103.00 129.00   0.50    3.50    --  111.50 125.00 -30.00   52
 53  ω    134.00 160.00   0.50    3.50    --  111.50 125.00 -30.00   52
 54  ω    112.00 138.00   0.50    3.50    --  111.50  30.00 120.00   52
 55  ω    146.00 172.00   0.50    3.50    --  111.50  30.00 120.00   52
 56  ω     73.00 100.00   0.50    3.50    --  111.50-125.00  60.00   54
 57  ω    134.00 165.00   0.50    3.50    --  111.50 125.00-120.00   62
 58  ω     86.00 111.00   0.50    3.50    --  111.50-125.00 -60.00   50
 59  ω    141.00 167.00   0.50    3.50    --  111.50  30.00  60.00   52
 60  ω    104.00 129.00   0.50    3.50    --  111.50  15.00 -30.00   50
 61  ω    138.00 164.00   0.50    3.50    --  111.50  15.00 -30.00   52
 62  ω     63.00  89.00   0.50    3.50    --  111.50 -77.00-180.00   52
 63  ω     80.00 105.00   0.50    3.50    --  111.50 -94.00-150.00   50
 64  ω     66.00 117.00   0.50    3.50    --  111.50-133.00 -14.21  102
 65  ω     80.00 105.00   0.50    3.50    --  111.50 -94.00 -98.68   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356676000
_diffrn_orient_matrix_UB_12      0.1366000000
_diffrn_orient_matrix_UB_13      -0.0188700000
_diffrn_orient_matrix_UB_21      0.0718997000
_diffrn_orient_matrix_UB_22      0.0128644000
_diffrn_orient_matrix_UB_23      -0.1231257000
_diffrn_orient_matrix_UB_31      -0.2616216000
_diffrn_orient_matrix_UB_32      0.0076084000
_diffrn_orient_matrix_UB_33      -0.0124470000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2923
_reflns_number_total             3406
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.057
_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)+(0.0956P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6706(2) 0.50282(13) 0.82777(11) 0.0383(3) Uani 1 1 d . . . . .
C2 C 0.7584(3) 0.43752(14) 0.92388(12) 0.0432(3) Uani 1 1 d . . . . .
H2 H 0.879534 0.462572 0.948280 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6667(3) 0.33668(14) 0.98234(13) 0.0447(3) Uani 1 1 d . . . . .
H3 H 0.723353 0.289837 1.047760 0.054 Uiso 1 1 calc R U . . .
C4 C 0.4889(3) 0.30491(14) 0.94342(12) 0.0431(3) Uani 1 1 d . . . . .
C5 C 0.4108(3) 0.37222(14) 0.84776(12) 0.0431(3) Uani 1 1 d . . . . .
H5 H 0.290438 0.348115 0.822001 0.052 Uiso 1 1 calc R U . . .
N6 N 0.4991(2) 0.47024(11) 0.79015(10) 0.0400(3) Uani 1 1 d . . . . .
N7 N 0.3892(3) 0.19834(13) 1.00224(12) 0.0516(3) Uani 1 1 d . . . . .
O8 O 0.4569(3) 0.14181(12) 1.08828(11) 0.0673(4) Uani 1 1 d . . . . .
O9 O 0.2385(3) 0.16955(13) 0.96326(11) 0.0660(4) Uani 1 1 d . . . . .
N10 N 0.7511(2) 0.60515(12) 0.76153(10) 0.0416(3) Uani 1 1 d . . . . .
H10 H 0.700(3) 0.6324(17) 0.6962(16) 0.043(4) Uiso 1 1 d . . . . .
C11 C 0.8922(2) 0.67302(13) 0.78521(12) 0.0405(3) Uani 1 1 d . . . . .
O12 O 0.9676(2) 0.64743(11) 0.87171(9) 0.0542(3) Uani 1 1 d . . . . .
C13 C 0.9392(3) 0.78217(14) 0.69609(12) 0.0437(3) Uani 1 1 d . . . . .
H13A H 0.793564 0.842790 0.694252 0.052 Uiso 1 1 calc R U . . .
H13B H 0.976853 0.760601 0.625121 0.052 Uiso 1 1 calc R U . . .
C14 C 1.1432(3) 0.83590(15) 0.71145(14) 0.0505(4) Uani 1 1 d . . . . .
H14A H 1.100001 0.863249 0.779636 0.061 Uiso 1 1 calc R U . . .
H14B H 1.285395 0.773341 0.719283 0.061 Uiso 1 1 calc R U . . .
C15 C 1.2044(4) 0.94005(16) 0.61757(16) 0.0602(5) Uani 1 1 d . . . . .
H15A H 1.245605 0.913842 0.549625 0.090 Uiso 1 1 calc R U . . .
H15B H 1.339985 0.969457 0.630388 0.090 Uiso 1 1 calc R U . . .
H15C H 1.067174 1.004236 0.611959 0.090 Uiso 1 1 calc R U . . .
C16 C 0.3546(2) 0.71337(13) 0.42639(11) 0.0392(3) Uani 1 1 d . . . . .
C17 C 0.1641(3) 0.68562(14) 0.39185(13) 0.0429(3) Uani 1 1 d . . . . .
H17 H 0.087670 0.620586 0.434881 0.052 Uiso 1 1 calc R U . . .
C18 C 0.0865(3) 0.75216(15) 0.29561(13) 0.0461(4) Uani 1 1 d . . . . .
H18 H -0.041890 0.731595 0.272496 0.055 Uiso 1 1 calc R U . . .
C19 C 0.1933(3) 0.84958(14) 0.23117(12) 0.0445(3) Uani 1 1 d . . . . .
C20 C 0.3851(3) 0.87720(14) 0.26647(13) 0.0458(3) Uani 1 1 d . . . . .
H20 H 0.461455 0.942470 0.223964 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4620(3) 0.81016(14) 0.36200(12) 0.0420(3) Uani 1 1 d . . . . .
H21 H 0.591413 0.829966 0.384984 0.050 Uiso 1 1 calc R U . . .
C22 C 0.4451(3) 0.64876(14) 0.52869(12) 0.0404(3) Uani 1 1 d . . . . .
O23 O 0.6185(2) 0.67156(12) 0.55466(9) 0.0536(3) Uani 1 1 d . . . . .
O24 O 0.3229(2) 0.56533(10) 0.59222(9) 0.0468(3) Uani 1 1 d . . . . .
H24 H 0.386(4) 0.532(2) 0.654(2) 0.064(6) Uiso 1 1 d . . . . .
N25 N 0.1202(4) 0.91562(16) 0.13500(14) 0.0599(4) Uani 1 1 d . . . . .
H25A H -0.004(5) 0.902(2) 0.125(2) 0.071(7) Uiso 1 1 d . . . . .
H25B H 0.165(4) 0.983(3) 0.096(2) 0.072(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.396(2) . ?
C1 N6 1.3491(18) . ?
C1 N10 1.3833(19) . ?
C2 C3 1.370(2) . ?
C3 C4 1.385(2) . ?
C4 C5 1.374(2) . ?
C4 N7 1.447(2) . ?
C5 N6 1.331(2) . ?
N7 O8 1.219(2) . ?
N7 O9 1.2325(19) . ?
N10 C11 1.3801(18) . ?
C11 O12 1.2155(18) . ?
C11 C13 1.504(2) . ?
C13 C14 1.520(2) . ?
C14 C15 1.515(3) . ?
C16 C17 1.396(2) . ?
C16 C21 1.396(2) . ?
C16 C22 1.466(2) . ?
C17 C18 1.377(2) . ?
C18 C19 1.400(2) . ?
C19 C20 1.407(2) . ?
C19 N25 1.365(2) . ?
C20 C21 1.370(2) . ?
C22 O23 1.2200(18) . ?
C22 O24 1.3263(18) . ?

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
N6 C1 C2 122.50(13) . . ?
N6 C1 N10 113.56(12) . . ?
N10 C1 C2 123.94(12) . . ?
C3 C2 C1 118.78(13) . . ?
C2 C3 C4 118.15(14) . . ?
C3 C4 N7 119.81(14) . . ?
C5 C4 C3 120.47(14) . . ?
C5 C4 N7 119.71(13) . . ?
N6 C5 C4 121.89(13) . . ?
C5 N6 C1 118.21(13) . . ?
O8 N7 C4 118.49(14) . . ?
O8 N7 O9 123.14(14) . . ?
O9 N7 C4 118.36(14) . . ?
C11 N10 C1 127.85(12) . . ?
N10 C11 C13 114.22(12) . . ?
O12 C11 N10 122.53(13) . . ?
O12 C11 C13 123.24(13) . . ?
C11 C13 C14 112.49(13) . . ?
C15 C14 C13 112.84(15) . . ?
C17 C16 C21 118.61(14) . . ?
C17 C16 C22 123.71(13) . . ?
C21 C16 C22 117.65(12) . . ?
C18 C17 C16 120.24(14) . . ?
C17 C18 C19 121.22(13) . . ?
C18 C19 C20 118.28(14) . . ?
N25 C19 C18 121.94(15) . . ?
N25 C19 C20 119.77(16) . . ?
C21 C20 C19 120.12(14) . . ?
C20 C21 C16 121.52(13) . . ?
O23 C22 C16 122.33(14) . . ?
O23 C22 O24 122.17(14) . . ?
O24 C22 C16 115.49(12) . . ?

_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 1.765
_oxdiff_exptl_absorpt_empirical_full_min 0.704
####################################################################### 
# 
# 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_650_auto
_database_code_depnum_ccdc_archive 'CCDC 2518012'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2023-02-04
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N O2, C9 H11 N3 O3'
_chemical_formula_sum            'C18 H22 N4 O5'
_chemical_formula_weight         374.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H22N4O5
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                   6.21761(15)
_cell_length_b                   12.5048(2)
_cell_length_c                   12.7578(4)
_cell_angle_alpha                79.345(2)
_cell_angle_beta                 78.280(3)
_cell_angle_gamma                80.4467(17)
_cell_volume                     945.96(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11948
_cell_measurement_temperature    200.0(1)
_cell_measurement_theta_max      79.4880
_cell_measurement_theta_min      3.6100
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             396
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.089
_diffrn_reflns_theta_min         3.582
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -74.00   0.50    2.00    --  -49.82-128.00 140.00   84
  2  ω    -89.00 -63.00   0.50    2.00    --  -49.82 142.00  25.00   52
  3  ω    -86.00 -60.00   0.50    2.00    --  -49.82 128.00-145.00   52
  4  ω   -111.00 -86.00   0.50    2.00    --  -49.82-142.00 -31.00   50
  5  ω     53.00 100.00   0.50    2.00    --   49.82-142.00 -31.00   94
  6  ω     37.00  96.00   0.50    2.00    --   49.82-128.00 140.00  118
  7  ω   -133.00-108.00   0.50    9.00    --  -90.00-142.00 -31.00   50
  8  ω   -135.00-110.00   0.50    9.00    --  -90.00-128.00 140.00   50
  9  ω    -84.00 -59.00   0.50    9.00    --  -90.00 142.00  25.00   50
 10  ω    -78.00 -53.00   0.50    9.00    --  -90.00 128.00-145.00   50
 11  ω    104.00 129.00   0.50    9.00    --  111.50 142.00  25.00   50
 12  ω     92.00 124.00   0.50    9.00    --  111.50-142.00 -31.00   64
 13  ω    122.00 149.00   0.50    9.00    --  111.50 128.00-145.00   54
 14  ω     71.00  96.00   0.50    9.00    --  111.50-128.00 140.00   50
 15  ω   -119.00 -31.00   0.50    2.00    --  -49.82 -77.00 120.00  176
 16  ω     -5.00  20.00   0.50    2.00    --  -49.82  19.00-120.00   50
 17  ω   -114.00 -73.00   0.50    2.00    --  -49.82-125.00 -60.00   82
 18  ω     29.00 119.00   0.50    2.00    --   49.82  77.00-150.00  180
 19  ω   -161.00 -90.00   0.50    9.00    --  -90.00 -15.00   0.00  142
 20  ω    -51.00 -26.00   0.50    9.00    --  -90.00  45.00-180.00   50
 21  ω    -46.00 -19.00   0.50    9.00    --  -90.00  45.00 150.00   54
 22  ω     46.00  91.00   0.50    9.00    --  111.50-125.00  90.00   90
 23  ω    142.00 178.00   0.50    9.00    --  111.50  45.00-150.00   72
 24  ω     41.00  66.00   0.50    9.00    --  111.50 -61.00 120.00   50
 25  ω    122.00 153.00   0.50    9.00    --  111.50 125.00   0.00   62
 26  ω    106.00 132.00   0.50    9.00    --  111.50  15.00-180.00   52
 27  ω     77.00 110.00   0.50    9.00    --  111.50-125.00  60.00   66
 28  ω     93.00 119.00   0.50    9.00    --  111.50  77.00 -90.00   52
 29  ω     77.00 111.00   0.50    9.00    --  111.50-125.00-180.00   68
 30  ω     80.00 108.00   0.50    9.00    --  111.50-125.00 120.00   56
 31  ω    111.00 159.00   0.50    9.00    --  111.50  30.00   0.00   96
 32  ω     82.00 111.00   0.50    9.00    --  111.50-125.00-150.00   58
 33  ω    144.00 170.00   0.50    9.00    --  111.50  61.00 120.00   52
 34  ω    112.00 175.00   0.50    9.00    --  111.50  77.00   0.00  126
 35  ω     50.00 101.00   0.50    9.00    --  111.50 -94.00 -90.00  102
 36  ω     48.00 102.00   0.50    9.00    --  111.50 -77.00 150.00  108
 37  ω     44.00 102.00   0.50    9.00    --  111.50-125.00   0.00  116
 38  ω    107.00 162.00   0.50    9.00    --  111.50  15.00-150.00  110
 39  ω     99.00 124.00   0.50    9.00    --  111.50 125.00 -60.00   50
 40  ω    138.00 164.00   0.50    9.00    --  111.50 125.00 -60.00   52
 41  ω     63.00  88.00   0.50    9.00    --  111.50 -77.00-150.00   50
 42  ω     52.00  96.00   0.50    9.00    --  111.50 -94.00  60.00   88
 43  ω     85.00 110.00   0.50    9.00    --  111.50 -79.00   0.93   50
 44  ω    125.00 177.00   0.50    9.00    --  111.50  77.00 -90.00  104
 45  ω     41.00  70.00   0.50    9.00    --  111.50 -61.00-120.00   58
 46  ω     41.00  66.00   0.50    9.00    --  111.50 -61.00  90.00   50
 47  ω     86.00 111.00   0.50    9.00    --  111.50-125.00-120.00   50
 48  ω     41.00  67.00   0.50    9.00    --  111.50 -61.00  60.00   52
 49  ω    106.00 176.00   0.50    9.00    --  111.50  30.00 -90.00  140
 50  ω     44.00  73.00   0.50    9.00    --  111.50-137.00-132.34   58
 51  ω     96.00 121.00   0.50    9.00    --  111.50-137.00-132.34   50
 52  ω    107.00 133.00   0.50    9.00    --  111.50  61.00 120.00   52
 53  ω     44.00 105.00   0.50    9.00    --  111.50-125.00  30.00  122
 54  ω    133.00 178.00   0.50    9.00    --  111.50 125.00 -30.00   90
 55  ω    100.00 126.00   0.50    9.00    --  111.50  77.00-180.00   52
 56  ω    152.00 178.00   0.50    9.00    --  111.50  77.00-180.00   52
 57  ω     84.00 109.00   0.50    9.00    --  111.50 -83.00 -46.94   50
 58  ω    130.00 170.00   0.50    9.00    --  111.50 125.00-180.00   80
 59  ω     51.00  76.00   0.50    9.00    --  111.50 -77.00-120.00   50
 60  ω     69.00  95.00   0.50    9.00    --  111.50 -77.00 -90.00   52
 61  ω     43.00 105.00   0.50    9.00    --  111.50-125.00 150.00  124
 62  ω    125.00 151.00   0.50    9.00    --  111.50  30.00  90.00   52
 63  ω    116.00 142.00   0.50    9.00    --  111.50 125.00-150.00   52
 64  ω    130.00 177.00   0.50    9.00    --  111.50 125.00-120.00   94
 65  ω    110.00 135.00   0.50    9.00    --  111.50 125.00  90.00   50
 66  ω    150.00 175.00   0.50    9.00    --  111.50 125.00  90.00   50
 67  ω    118.00 143.00   0.50    9.00    --  111.50 125.00 150.00   50
 68  ω     92.00 153.00   0.50    9.00    --  111.50  77.00 -60.00  122
 69  ω    104.00 131.00   0.50    9.00    --  111.50  77.00  60.00   54
 70  ω    103.00 139.00   0.50    9.00    --  111.50  77.00 120.00   72
 71  ω    107.00 133.00   0.50    9.00    --  111.50  77.00 150.00   52
 72  ω     44.00  70.00   0.50    9.00    --  111.50 -79.00   0.93   52
 73  ω     79.00 104.00   0.50    9.00    --  111.50 -94.00-150.00   50
 74  ω     50.00  77.00   0.50    9.00    --  111.50 -86.00 -52.04   54
 75  ω     90.00 128.00   0.50    9.00    --  111.50 -86.00 -52.04   76
 76  ω    107.00 132.00   0.50    9.00    --  111.50 -88.00-122.12   50
 77  ω     43.00  69.00   0.50    9.00    --  111.50 -61.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0550673000
_diffrn_orient_matrix_UB_12      0.0249981000
_diffrn_orient_matrix_UB_13      -0.1246221000
_diffrn_orient_matrix_UB_21      0.2488867000
_diffrn_orient_matrix_UB_22      -0.0155489000
_diffrn_orient_matrix_UB_23      0.0051280000
_diffrn_orient_matrix_UB_31      0.0147659000
_diffrn_orient_matrix_UB_32      -0.1230173000
_diffrn_orient_matrix_UB_33      -0.0058687000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3741
_reflns_number_total             4064
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.103
_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)+(0.0591P)²+0.1357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.71629(16) 0.55713(8) 0.32375(8) 0.0301(2) Uani 1 1 d . . . . .
C2 C 0.89808(19) 0.56842(9) 0.36610(9) 0.0368(2) Uani 1 1 d . . . . .
H2 H 0.946028 0.515369 0.423135 0.044 Uiso 1 1 calc R U . . .
C3 C 1.00838(19) 0.65856(9) 0.32361(10) 0.0398(2) Uani 1 1 d . . . . .
H3 H 1.133550 0.667063 0.351864 0.048 Uiso 1 1 calc R U . . .
C4 C 0.94006(18) 0.73626(8) 0.24104(9) 0.0368(2) Uani 1 1 d . . . . .
H4 H 1.017464 0.797925 0.214026 0.044 Uiso 1 1 calc R U . . .
C5 C 0.75727(18) 0.72552(8) 0.19622(8) 0.0336(2) Uani 1 1 d . . . . .
C6 C 0.64628(17) 0.63358(8) 0.23953(8) 0.0317(2) Uani 1 1 d . . . . .
H6 H 0.522493 0.623667 0.210998 0.038 Uiso 1 1 calc R U . . .
C7 C 0.59619(17) 0.45983(8) 0.36649(8) 0.0321(2) Uani 1 1 d . . . . .
O8 O 0.44260(14) 0.44129(6) 0.33003(7) 0.0423(2) Uani 1 1 d . . . . .
O9 O 0.67740(14) 0.39414(6) 0.44688(7) 0.0416(2) Uani 1 1 d . . . . .
H9 H 0.603(3) 0.3355(16) 0.4671(15) 0.068(5) Uiso 1 1 d . . . . .
N10 N 0.68721(18) 0.80464(8) 0.11464(9) 0.0469(3) Uani 1 1 d . . . . .
C11 C 0.5220(2) 0.78306(12) 0.05937(11) 0.0550(3) Uani 1 1 d . . . . .
H11A H 0.579489 0.719094 0.022814 0.083 Uiso 1 1 calc R U . . .
H11B H 0.486456 0.847150 0.005655 0.083 Uiso 1 1 calc R U . . .
H11C H 0.387756 0.768266 0.112110 0.083 Uiso 1 1 calc R U . . .
C12 C 0.8293(2) 0.88601(10) 0.05841(11) 0.0528(3) Uani 1 1 d . . . . .
H12A H 0.847773 0.932279 0.109292 0.079 Uiso 1 1 calc R U . . .
H12B H 0.761883 0.931788 -0.000648 0.079 Uiso 1 1 calc R U . . .
H12C H 0.974448 0.848976 0.028563 0.079 Uiso 1 1 calc R U . . .
N13 N 0.49179(15) 0.21135(7) 0.52474(7) 0.0327(2) Uani 1 1 d . . . . .
C14 C 0.32267(17) 0.17483(8) 0.49730(8) 0.0311(2) Uani 1 1 d . . . . .
C15 C 0.23523(18) 0.07994(8) 0.55534(8) 0.0340(2) Uani 1 1 d . . . . .
H15 H 0.113640 0.056063 0.535740 0.041 Uiso 1 1 calc R U . . .
C16 C 0.32980(18) 0.02259(8) 0.64104(8) 0.0348(2) Uani 1 1 d . . . . .
H16 H 0.275032 -0.041982 0.681816 0.042 Uiso 1 1 calc R U . . .
C17 C 0.50615(18) 0.06047(8) 0.66698(8) 0.0331(2) Uani 1 1 d . . . . .
C18 C 0.58189(18) 0.15532(8) 0.60780(9) 0.0340(2) Uani 1 1 d . . . . .
H18 H 0.701652 0.181166 0.627026 0.041 Uiso 1 1 calc R U . . .
N19 N 0.24797(16) 0.23889(7) 0.40796(7) 0.0349(2) Uani 1 1 d . . . . .
H19 H 0.308(2) 0.2986(13) 0.3844(12) 0.044(4) Uiso 1 1 d . . . . .
C20 C 0.10174(18) 0.21595(8) 0.35005(9) 0.0345(2) Uani 1 1 d . . . . .
C21 C 0.0805(2) 0.29676(9) 0.24794(9) 0.0382(2) Uani 1 1 d . . . . .
H21A H 0.225734 0.293824 0.198568 0.046 Uiso 1 1 calc R U . . .
H21B H 0.041172 0.371810 0.266621 0.046 Uiso 1 1 calc R U . . .
C22 C -0.0932(2) 0.27457(11) 0.18912(11) 0.0494(3) Uani 1 1 d . . . . .
H22A H -0.050001 0.201244 0.166575 0.059 Uiso 1 1 calc R U . . .
H22B H -0.237256 0.273823 0.239361 0.059 Uiso 1 1 calc R U . . .
C23 C -0.1196(3) 0.36050(14) 0.09000(13) 0.0665(4) Uani 1 1 d . . . . .
H23A H 0.023315 0.362503 0.040715 0.100 Uiso 1 1 calc R U . . .
H23B H -0.170861 0.432632 0.112469 0.100 Uiso 1 1 calc R U . . .
H23C H -0.228387 0.341846 0.052806 0.100 Uiso 1 1 calc R U . . .
O24 O 0.00256(15) 0.13649(7) 0.37793(7) 0.0474(2) Uani 1 1 d . . . . .
N25 N 0.61230(17) 0.00300(7) 0.75638(8) 0.0392(2) Uani 1 1 d . . . . .
O26 O 0.76677(16) 0.04012(7) 0.77710(8) 0.0510(2) Uani 1 1 d . . . . .
O27 O 0.54240(17) -0.08135(7) 0.80702(7) 0.0529(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3851(14) . ?
C1 C6 1.3892(14) . ?
C1 C7 1.4920(13) . ?
C2 C3 1.3836(15) . ?
C3 C4 1.3786(16) . ?
C4 C5 1.4071(15) . ?
C5 C6 1.4060(14) . ?
C5 N10 1.3828(14) . ?
C7 O8 1.2149(13) . ?
C7 O9 1.3202(12) . ?
N10 C11 1.4430(17) . ?
N10 C12 1.4499(15) . ?
N13 C14 1.3435(13) . ?
N13 C18 1.3281(14) . ?
C14 C15 1.4062(13) . ?
C14 N19 1.3822(13) . ?
C15 C16 1.3736(15) . ?
C16 C17 1.3835(15) . ?
C17 C18 1.3814(14) . ?
C17 N25 1.4486(14) . ?
N19 C20 1.3757(14) . ?
C20 C21 1.5081(15) . ?
C20 O24 1.2156(13) . ?
C21 C22 1.5208(16) . ?
C22 C23 1.518(2) . ?
N25 O26 1.2265(13) . ?
N25 O27 1.2268(13) . ?

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
C2 C1 C6 121.15(9) . . ?
C2 C1 C7 119.93(9) . . ?
C6 C1 C7 118.90(9) . . ?
C3 C2 C1 118.63(10) . . ?
C4 C3 C2 121.23(10) . . ?
C3 C4 C5 120.92(9) . . ?
C6 C5 C4 117.56(9) . . ?
N10 C5 C4 120.67(10) . . ?
N10 C5 C6 121.74(10) . . ?
C1 C6 C5 120.49(9) . . ?
O8 C7 C1 123.83(9) . . ?
O8 C7 O9 123.19(9) . . ?
O9 C7 C1 112.96(9) . . ?
C5 N10 C11 119.01(10) . . ?
C5 N10 C12 119.58(11) . . ?
C11 N10 C12 117.42(10) . . ?
C18 N13 C14 119.20(9) . . ?
N13 C14 C15 121.87(10) . . ?
N13 C14 N19 113.41(9) . . ?
N19 C14 C15 124.72(9) . . ?
C16 C15 C14 118.42(9) . . ?
C15 C16 C17 118.87(9) . . ?
C16 C17 N25 121.13(9) . . ?
C18 C17 C16 119.85(10) . . ?
C18 C17 N25 119.02(10) . . ?
N13 C18 C17 121.77(10) . . ?
C20 N19 C14 127.86(9) . . ?
N19 C20 C21 113.82(9) . . ?
O24 C20 N19 122.80(10) . . ?
O24 C20 C21 123.37(10) . . ?
C20 C21 C22 113.03(10) . . ?
C23 C22 C21 111.91(12) . . ?
O26 N25 C17 118.90(9) . . ?
O26 N25 O27 123.54(10) . . ?
O27 N25 C17 117.56(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 1.670
_oxdiff_exptl_absorpt_empirical_full_min 0.612
####################################################################### 
# 
# 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_674_auto
_database_code_depnum_ccdc_archive 'CCDC 2518013'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;Kansas State University
United States of America
;
_audit_update_record             
;
2025-12-21 deposited with the CCDC.	2026-03-16 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         ?
_chemical_formula_sum            'C19 H24 N4 O5'
_chemical_formula_weight         388.42

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                   6.35274(15)
_cell_length_b                   12.46903(18)
_cell_length_c                   12.9378(3)
_cell_angle_alpha                97.3653(16)
_cell_angle_beta                 103.862(2)
_cell_angle_gamma                99.5009(15)
_cell_volume                     966.16(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.815
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37103
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.574
_diffrn_reflns_theta_max         80.154
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4176
_reflns_number_gt                3858
_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)+(0.0655P)²+0.1549P] 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         4176
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
C1 C 0.44433(16) 0.55889(8) 0.67249(8) 0.0314(2) Uani 1 1 d . . . . .
C2 C 0.22747(18) 0.56984(9) 0.63227(9) 0.0391(2) Uani 1 1 d . . . . .
H2 H 0.127568 0.515929 0.575567 0.047 Uiso 1 1 calc R U . . .
C3 C 0.15963(19) 0.66090(10) 0.67644(10) 0.0421(3) Uani 1 1 d . . . . .
H3 H 0.011304 0.669096 0.649744 0.051 Uiso 1 1 calc R U . . .
C4 C 0.30322(19) 0.73997(9) 0.75848(10) 0.0392(2) Uani 1 1 d . . . . .
H4 H 0.252937 0.802194 0.786717 0.047 Uiso 1 1 calc R U . . .
C5 C 0.52303(18) 0.72975(9) 0.80089(9) 0.0349(2) Uani 1 1 d . . . . .
C6 C 0.59114(17) 0.63697(8) 0.75609(8) 0.0324(2) Uani 1 1 d . . . . .
H6 H 0.738500 0.627525 0.783091 0.039 Uiso 1 1 calc R U . . .
C7 C 0.52183(17) 0.46048(8) 0.62876(8) 0.0332(2) Uani 1 1 d . . . . .
O8 O 0.70698(13) 0.44340(6) 0.66344(7) 0.0426(2) Uani 1 1 d . . . . .
O9 O 0.36826(13) 0.39217(7) 0.54995(7) 0.0426(2) Uani 1 1 d . . . . .
H9 H 0.420(3) 0.3329(16) 0.5279(15) 0.070(5) Uiso 1 1 d . . . . .
N10 N 0.66787(18) 0.81007(9) 0.88200(9) 0.0496(3) Uani 1 1 d . . . . .
C11 C 0.5846(3) 0.89309(11) 0.94022(12) 0.0569(3) Uani 1 1 d . . . . .
H11A H 0.514595 0.937374 0.889956 0.085 Uiso 1 1 calc R U . . .
H11B H 0.707513 0.941123 0.996562 0.085 Uiso 1 1 calc R U . . .
H11C H 0.475431 0.857047 0.973607 0.085 Uiso 1 1 calc R U . . .
C12 C 0.8824(2) 0.79021(12) 0.93380(11) 0.0527(3) Uani 1 1 d . . . . .
H12B H 0.963050 0.853446 0.990486 0.079 Uiso 1 1 calc R U . . .
H12C H 0.966366 0.780225 0.880071 0.079 Uiso 1 1 calc R U . . .
H12A H 0.863497 0.723466 0.966000 0.079 Uiso 1 1 calc R U . . .
C13 C 0.67085(18) 0.17094(8) 0.49857(8) 0.0331(2) Uani 1 1 d . . . . .
C14 C 0.70454(19) 0.07465(9) 0.44081(9) 0.0371(2) Uani 1 1 d . . . . .
H14 H 0.841376 0.051217 0.460417 0.045 Uiso 1 1 calc R U . . .
C15 C 0.5348(2) 0.01518(9) 0.35527(9) 0.0389(2) Uani 1 1 d . . . . .
H15 H 0.551911 -0.050302 0.314558 0.047 Uiso 1 1 calc R U . . .
C16 C 0.33788(19) 0.05274(9) 0.32958(9) 0.0375(2) Uani 1 1 d . . . . .
C17 C 0.31668(18) 0.14873(9) 0.38881(9) 0.0370(2) Uani 1 1 d . . . . .
H17 H 0.181829 0.174082 0.369913 0.044 Uiso 1 1 calc R U . . .
N18 N 0.48037(15) 0.20673(7) 0.47179(7) 0.0349(2) Uani 1 1 d . . . . .
N19 N 0.82514(16) 0.23733(8) 0.58736(8) 0.0365(2) Uani 1 1 d . . . . .
H19 H 0.785(3) 0.2986(14) 0.6116(13) 0.052(4) Uiso 1 1 d . . . . .
C20 C 1.02258(18) 0.21655(9) 0.64444(9) 0.0356(2) Uani 1 1 d . . . . .
C21 C 1.13458(18) 0.30127(9) 0.74563(9) 0.0379(2) Uani 1 1 d . . . . .
H21A H 1.040682 0.296655 0.796560 0.045 Uiso 1 1 calc R U . . .
H21B H 1.146237 0.375916 0.726309 0.045 Uiso 1 1 calc R U . . .
C22 C 1.36389(19) 0.28666(10) 0.80219(9) 0.0406(3) Uani 1 1 d . . . . .
H22A H 1.455949 0.286624 0.750332 0.049 Uiso 1 1 calc R U . . .
H22B H 1.352030 0.214319 0.826515 0.049 Uiso 1 1 calc R U . . .
C23 C 1.4767(2) 0.37800(10) 0.89930(10) 0.0454(3) Uani 1 1 d . . . . .
H23A H 1.473551 0.450510 0.876162 0.054 Uiso 1 1 calc R U . . .
H23B H 1.392394 0.372925 0.954291 0.054 Uiso 1 1 calc R U . . .
C24 C 1.7142(3) 0.37197(16) 0.95006(14) 0.0696(4) Uani 1 1 d . . . . .
H24A H 1.773011 0.426624 1.016824 0.104 Uiso 1 1 calc R U . . .
H24B H 1.803431 0.387516 0.899500 0.104 Uiso 1 1 calc R U . . .
H24C H 1.720139 0.297869 0.966746 0.104 Uiso 1 1 calc R U . . .
O25 O 1.09575(15) 0.13681(7) 0.61693(7) 0.0498(2) Uani 1 1 d . . . . .
N26 N 0.15344(18) -0.00672(8) 0.23994(8) 0.0453(2) Uani 1 1 d . . . . .
O27 O 0.17657(18) -0.09153(8) 0.18866(8) 0.0612(3) Uani 1 1 d . . . . .
O28 O -0.01775(16) 0.02994(8) 0.21979(8) 0.0579(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3872(14) . ?
C1 C6 1.3909(14) . ?
C1 C7 1.4910(13) . ?
C2 C3 1.3837(15) . ?
C3 C4 1.3790(17) . ?
C4 C5 1.4060(16) . ?
C5 N10 1.3837(14) . ?
C5 C6 1.4054(14) . ?
C7 O8 1.2184(13) . ?
C7 O9 1.3203(13) . ?
N10 C12 1.4438(17) . ?
N10 C11 1.4457(16) . ?
C13 N18 1.3419(14) . ?
C13 N19 1.3837(13) . ?
C13 C14 1.4061(14) . ?
C14 C15 1.3751(16) . ?
C15 C16 1.3889(16) . ?
C16 C17 1.3803(15) . ?
C16 N26 1.4523(14) . ?
C17 N18 1.3322(14) . ?
N19 C20 1.3777(14) . ?
C20 O25 1.2135(13) . ?
C20 C21 1.5122(15) . ?
C21 C22 1.5171(15) . ?
C22 C23 1.5237(16) . ?
C23 C24 1.5129(18) . ?
N26 O27 1.2240(14) . ?
N26 O28 1.2322(14) . ?

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
C2 C1 C6 121.05(9) . . ?
C2 C1 C7 120.15(9) . . ?
C6 C1 C7 118.77(9) . . ?
C3 C2 C1 118.64(10) . . ?
C4 C3 C2 121.26(10) . . ?
C3 C4 C5 120.89(10) . . ?
N10 C5 C6 121.48(10) . . ?
N10 C5 C4 120.80(10) . . ?
C6 C5 C4 117.70(10) . . ?
C1 C6 C5 120.46(9) . . ?
O8 C7 O9 123.12(9) . . ?
O8 C7 C1 123.54(9) . . ?
O9 C7 C1 113.32(9) . . ?
C5 N10 C12 119.33(10) . . ?
C5 N10 C11 120.05(11) . . ?
C12 N10 C11 117.16(11) . . ?
N18 C13 N19 113.35(9) . . ?
N18 C13 C14 122.04(10) . . ?
N19 C13 C14 124.61(10) . . ?
C15 C14 C13 118.45(10) . . ?
C14 C15 C16 118.70(10) . . ?
C17 C16 C15 119.90(10) . . ?
C17 C16 N26 119.10(10) . . ?
C15 C16 N26 121.00(10) . . ?
N18 C17 C16 121.72(10) . . ?
C17 N18 C13 119.17(9) . . ?
C20 N19 C13 128.05(9) . . ?
O25 C20 N19 123.00(10) . . ?
O25 C20 C21 123.76(10) . . ?
N19 C20 C21 113.22(9) . . ?
C20 C21 C22 113.62(9) . . ?
C21 C22 C23 111.90(10) . . ?
C24 C23 C22 112.86(11) . . ?
O27 N26 O28 123.45(11) . . ?
O27 N26 C16 117.80(10) . . ?
O28 N26 C16 118.75(10) . . ?

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
C14 H14 O25 0.95 2.27 2.8578(14) 119.2 . yes
C14 H14 O25 0.95 2.56 3.1895(13) 123.9 2_756 yes
C15 H15 O25 0.95 2.66 3.2355(14) 119.9 2_756 yes
C12 H12B O27 0.98 2.54 3.3808(16) 143.6 1_666 yes
N19 H19 O8 0.887(17) 2.026(17) 2.9115(12) 176.8(14) . yes
O9 H9 N18 0.90(2) 1.79(2) 2.6768(12) 171.4(18) . yes

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042

