# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2075232'
loop_
_audit_author_name
_audit_author_address
'Yu Duan'
;Jiamusi University
China
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N5 O3, C7 H5 O4, 2(H2 O)'
_chemical_formula_sum            'C21 H27 N5 O9'
_chemical_formula_weight         493.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3506(8)
_cell_length_b                   18.9562(17)
_cell_length_c                   12.9324(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.673(9)
_cell_angle_gamma                90
_cell_volume                     2259.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2123
_cell_measurement_theta_min      3.8930
_cell_measurement_theta_max      24.3930

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             1040.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.37777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_reflns_number            15896
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.372
_diffrn_reflns_theta_max         29.713
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5439
_reflns_number_gt                2644
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6411
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1768(2) -0.01377(9) 0.55617(14) 0.0550(5) Uani 1 1 d G . . . .
H1A H 0.2161 -0.0543 0.5572 0.082 Uiso 1 1 d G U . . .
H1B H 0.2354 0.0150 0.5914 0.082 Uiso 1 1 d G U . . .
N1 N 0.6021(2) 0.05483(10) 0.86679(14) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.6703(2) -0.01563(10) 0.73848(15) 0.0442(5) Uani 1 1 d . . . . .
O2 O 0.2149(2) 0.35450(9) 0.92611(14) 0.0593(5) Uani 1 1 d . . . . .
N3 N 0.5280(2) 0.12589(10) 0.99393(14) 0.0416(5) Uani 1 1 d . . . . .
O3 O 0.1152(2) 0.04544(11) 0.93008(14) 0.0668(6) Uani 1 1 d . . . . .
N4 N 0.4372(2) -0.02849(11) 0.76953(15) 0.0455(5) Uani 1 1 d . . . . .
N5 N 0.8886(2) -0.06433(10) 0.62699(14) 0.0448(5) Uani 1 1 d . . . . .
H5A H 0.8750 -0.0359 0.5714 0.054 Uiso 1 1 calc R U . . .
H5B H 0.9615 -0.0934 0.6209 0.054 Uiso 1 1 calc R U . . .
O4 O 0.4331(2) 0.22353(11) 0.74972(17) 0.0665(6) Uani 1 1 d . . . . .
H4 H 0.4617 0.2602 0.7798 0.100 Uiso 1 1 calc R U . . .
C1 C 0.2898(3) 0.21650(13) 0.74882(18) 0.0416(6) Uani 1 1 d . . . . .
O5 O 0.2969(2) 0.11982(10) 0.62949(15) 0.0646(6) Uani 1 1 d . . . . .
H5 H 0.3760 0.1377 0.6263 0.097 Uiso 1 1 calc R U . . .
C2 C 0.5676(3) 0.00507(12) 0.79318(18) 0.0395(6) Uani 1 1 d . . . . .
C3 C 0.3547(3) 0.04731(12) 0.89531(17) 0.0375(6) Uani 1 1 d . . . . .
C4 C 0.4952(3) 0.07512(12) 0.91643(17) 0.0361(6) Uani 1 1 d . . . . .
O6 O 0.0410(2) 0.13224(12) 1.05921(16) 0.0727(6) Uani 1 1 d . . . . .
H6 H 0.0399 0.0991 1.0184 0.109 Uiso 1 1 calc R U . . .
C5 C 0.2111(3) 0.25914(12) 0.80626(18) 0.0399(6) Uani 1 1 d . . . . .
O7 O 0.4148(2) 0.33075(10) 0.86209(17) 0.0708(6) Uani 1 1 d . . . . .
O8 O 0.2017(2) 0.20635(11) 1.14334(15) 0.0684(6) Uani 1 1 d . . . . .
C6 C 0.3366(3) -0.00643(13) 0.82044(17) 0.0442(6) Uani 1 1 d . . . . .
H6A H 0.2462 -0.0281 0.8058 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2805(3) 0.12761(13) 1.02166(17) 0.0430(6) Uani 1 1 d . . . . .
C8 C 0.2408(3) 0.07141(14) 0.94765(18) 0.0446(6) Uani 1 1 d . . . . .
C9 C 0.4200(3) 0.15045(13) 1.04134(18) 0.0451(6) Uani 1 1 d . . . . .
H9 H 0.4429 0.1857 1.0913 0.054 Uiso 1 1 calc R U . . .
C10 C 0.9270(3) -0.02138(14) 0.72440(19) 0.0477(7) Uani 1 1 d . . . . .
H10A H 1.0111 0.0075 0.7191 0.057 Uiso 1 1 calc R U . . .
H10B H 0.9521 -0.0526 0.7841 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2841(3) 0.31886(13) 0.8706(2) 0.0461(7) Uani 1 1 d . . . . .
C12 C 0.7549(3) -0.10601(13) 0.62961(19) 0.0464(7) Uani 1 1 d . . . . .
H12A H 0.7722 -0.1396 0.6870 0.056 Uiso 1 1 calc R U . . .
H12B H 0.7301 -0.1323 0.5647 0.056 Uiso 1 1 calc R U . . .
C13 C 0.6312(3) -0.05869(13) 0.64347(19) 0.0483(7) Uani 1 1 d . . . . .
H13A H 0.6075 -0.0282 0.5828 0.058 Uiso 1 1 calc R U . . .
H13B H 0.5463 -0.0870 0.6491 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6786(3) 0.15223(13) 1.0248(2) 0.0504(7) Uani 1 1 d . . . . .
H14A H 0.7459 0.1141 1.0185 0.061 Uiso 1 1 calc R U . . .
H14B H 0.6930 0.1667 1.0977 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0634(3) 0.24750(13) 0.8000(2) 0.0563(7) Uani 1 1 d . . . . .
H15 H 0.0102 0.2748 0.8397 0.068 Uiso 1 1 calc R U . . .
C16 C 0.8034(3) 0.02534(14) 0.7416(2) 0.0517(7) Uani 1 1 d . . . . .
H16A H 0.8274 0.0486 0.8091 0.062 Uiso 1 1 calc R U . . .
H16B H 0.7882 0.0614 0.6877 0.062 Uiso 1 1 calc R U . . .
C17 C 0.1729(3) 0.15904(16) 1.0796(2) 0.0535(7) Uani 1 1 d . . . . .
O18 O 0.4361(3) -0.15392(12) 0.40754(19) 0.0912(8) Uani 1 1 d G . . . .
H18A H 0.3959 -0.1529 0.4618 0.137 Uiso 1 1 d G U . . .
H18B H 0.4122 -0.1917 0.3735 0.137 Uiso 1 1 d G U . . .
C19 C 0.0740(3) 0.15431(15) 0.6769(2) 0.0637(8) Uani 1 1 d . . . . .
H19 H 0.0267 0.1202 0.6320 0.076 Uiso 1 1 calc R U . . .
C20 C 0.2211(3) 0.16280(13) 0.68466(19) 0.0459(7) Uani 1 1 d . . . . .
C21 C 0.7121(3) 0.21330(15) 0.9588(3) 0.0716(9) Uani 1 1 d . . . . .
H21A H 0.7033 0.1986 0.8870 0.107 Uiso 1 1 calc R U . . .
H21B H 0.8092 0.2294 0.9832 0.107 Uiso 1 1 calc R U . . .
H21C H 0.6451 0.2510 0.9639 0.107 Uiso 1 1 calc R U . . .
C22 C -0.0046(3) 0.19552(16) 0.7348(3) 0.0733(9) Uani 1 1 d . . . . .
H22 H -0.1038 0.1883 0.7300 0.088 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1A 0.8501 . ?
O1 H1B 0.8500 . ?
N1 C4 1.332(3) . ?
N1 C2 1.340(3) . ?
N2 C2 1.343(3) . ?
N2 C16 1.462(3) . ?
N2 C13 1.469(3) . ?
O2 C11 1.243(3) . ?
N3 C9 1.349(3) . ?
N3 C4 1.386(3) . ?
N3 C14 1.485(3) . ?
O3 C8 1.258(3) . ?
N4 C6 1.304(3) . ?
N4 C2 1.364(3) . ?
N5 C12 1.484(3) . ?
N5 C10 1.492(3) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
O4 C1 1.344(3) . ?
O4 H4 0.8200 . ?
C1 C5 1.389(3) . ?
C1 C20 1.399(3) . ?
O5 C20 1.358(3) . ?
O5 H5 0.8200 . ?
C3 C6 1.396(3) . ?
C3 C4 1.399(3) . ?
C3 C8 1.430(3) . ?
O6 C17 1.319(3) . ?
O6 H6 0.8200 . ?
C5 C15 1.388(3) . ?
C5 C11 1.500(3) . ?
O7 C11 1.266(3) . ?
O8 C17 1.217(3) . ?
C6 H6A 0.9300 . ?
C7 C9 1.357(3) . ?
C7 C8 1.439(4) . ?
C7 C17 1.478(4) . ?
C9 H9 0.9300 . ?
C10 C16 1.502(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.498(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C21 1.502(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C22 1.380(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
O18 H18A 0.8501 . ?
O18 H18B 0.8500 . ?
C19 C20 1.372(4) . ?
C19 C22 1.377(4) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A O1 H1B 109.5 . . ?
C4 N1 C2 115.8(2) . . ?
C2 N2 C16 120.7(2) . . ?
C2 N2 C13 120.2(2) . . ?
C16 N2 C13 114.16(19) . . ?
C9 N3 C4 118.5(2) . . ?
C9 N3 C14 120.7(2) . . ?
C4 N3 C14 120.8(2) . . ?
C6 N4 C2 115.5(2) . . ?
C12 N5 C10 110.80(18) . . ?
C12 N5 H5A 109.5 . . ?
C10 N5 H5A 109.5 . . ?
C12 N5 H5B 109.5 . . ?
C10 N5 H5B 109.5 . . ?
H5A N5 H5B 108.1 . . ?
C1 O4 H4 109.5 . . ?
O4 C1 C5 123.7(2) . . ?
O4 C1 C20 115.8(2) . . ?
C5 C1 C20 120.6(2) . . ?
C20 O5 H5 109.5 . . ?
N1 C2 N2 118.1(2) . . ?
N1 C2 N4 126.0(2) . . ?
N2 C2 N4 115.9(2) . . ?
C6 C3 C4 114.3(2) . . ?
C6 C3 C8 123.2(2) . . ?
C4 C3 C8 122.5(2) . . ?
N1 C4 N3 117.2(2) . . ?
N1 C4 C3 123.6(2) . . ?
N3 C4 C3 119.3(2) . . ?
C17 O6 H6 109.5 . . ?
C15 C5 C1 119.2(2) . . ?
C15 C5 C11 120.5(2) . . ?
C1 C5 C11 120.3(2) . . ?
N4 C6 C3 124.8(2) . . ?
N4 C6 H6A 117.6 . . ?
C3 C6 H6A 117.6 . . ?
C9 C7 C8 119.6(2) . . ?
C9 C7 C17 119.4(3) . . ?
C8 C7 C17 120.9(2) . . ?
O3 C8 C3 122.4(2) . . ?
O3 C8 C7 122.6(2) . . ?
C3 C8 C7 115.0(2) . . ?
N3 C9 C7 125.0(2) . . ?
N3 C9 H9 117.5 . . ?
C7 C9 H9 117.5 . . ?
N5 C10 C16 111.4(2) . . ?
N5 C10 H10A 109.3 . . ?
C16 C10 H10A 109.3 . . ?
N5 C10 H10B 109.3 . . ?
C16 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O2 C11 O7 123.8(2) . . ?
O2 C11 C5 119.9(2) . . ?
O7 C11 C5 116.2(2) . . ?
N5 C12 C13 110.8(2) . . ?
N5 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 C12 110.1(2) . . ?
N2 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
N3 C14 C21 112.7(2) . . ?
N3 C14 H14A 109.1 . . ?
C21 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C21 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C22 C15 C5 120.1(3) . . ?
C22 C15 H15 120.0 . . ?
C5 C15 H15 120.0 . . ?
N2 C16 C10 110.8(2) . . ?
N2 C16 H16A 109.5 . . ?
C10 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
O8 C17 O6 120.8(3) . . ?
O8 C17 C7 123.3(3) . . ?
O6 C17 C7 115.9(3) . . ?
H18A O18 H18B 109.5 . . ?
C20 C19 C22 120.9(3) . . ?
C20 C19 H19 119.5 . . ?
C22 C19 H19 119.5 . . ?
O5 C20 C19 119.8(2) . . ?
O5 C20 C1 121.3(2) . . ?
C19 C20 C1 118.9(3) . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 C15 120.3(3) . . ?
C19 C22 H22 119.9 . . ?
C15 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C2 N2 177.9(2) . . . . ?
C4 N1 C2 N4 -3.8(3) . . . . ?
C16 N2 C2 N1 -13.7(3) . . . . ?
C13 N2 C2 N1 -167.5(2) . . . . ?
C16 N2 C2 N4 167.8(2) . . . . ?
C13 N2 C2 N4 14.1(3) . . . . ?
C6 N4 C2 N1 3.9(4) . . . . ?
C6 N4 C2 N2 -177.8(2) . . . . ?
C2 N1 C4 N3 179.22(19) . . . . ?
C2 N1 C4 C3 0.2(3) . . . . ?
C9 N3 C4 N1 176.2(2) . . . . ?
C14 N3 C4 N1 -4.3(3) . . . . ?
C9 N3 C4 C3 -4.7(3) . . . . ?
C14 N3 C4 C3 174.8(2) . . . . ?
C6 C3 C4 N1 2.8(3) . . . . ?
C8 C3 C4 N1 -178.2(2) . . . . ?
C6 C3 C4 N3 -176.2(2) . . . . ?
C8 C3 C4 N3 2.8(3) . . . . ?
O4 C1 C5 C15 -179.9(2) . . . . ?
C20 C1 C5 C15 0.5(4) . . . . ?
O4 C1 C5 C11 2.6(4) . . . . ?
C20 C1 C5 C11 -176.9(2) . . . . ?
C2 N4 C6 C3 -0.4(4) . . . . ?
C4 C3 C6 N4 -2.7(4) . . . . ?
C8 C3 C6 N4 178.3(2) . . . . ?
C6 C3 C8 O3 0.3(4) . . . . ?
C4 C3 C8 O3 -178.6(2) . . . . ?
C6 C3 C8 C7 -179.6(2) . . . . ?
C4 C3 C8 C7 1.5(3) . . . . ?
C9 C7 C8 O3 176.2(2) . . . . ?
C17 C7 C8 O3 -1.4(4) . . . . ?
C9 C7 C8 C3 -3.9(3) . . . . ?
C17 C7 C8 C3 178.4(2) . . . . ?
C4 N3 C9 C7 2.3(4) . . . . ?
C14 N3 C9 C7 -177.2(2) . . . . ?
C8 C7 C9 N3 2.2(4) . . . . ?
C17 C7 C9 N3 179.9(2) . . . . ?
C12 N5 C10 C16 -55.6(3) . . . . ?
C15 C5 C11 O2 6.3(4) . . . . ?
C1 C5 C11 O2 -176.3(2) . . . . ?
C15 C5 C11 O7 -171.9(2) . . . . ?
C1 C5 C11 O7 5.5(3) . . . . ?
C10 N5 C12 C13 57.3(2) . . . . ?
C2 N2 C13 C12 -149.5(2) . . . . ?
C16 N2 C13 C12 55.1(3) . . . . ?
N5 C12 C13 N2 -56.0(3) . . . . ?
C9 N3 C14 C21 -92.8(3) . . . . ?
C4 N3 C14 C21 87.7(3) . . . . ?
C1 C5 C15 C22 -2.0(4) . . . . ?
C11 C5 C15 C22 175.5(2) . . . . ?
C2 N2 C16 C10 151.3(2) . . . . ?
C13 N2 C16 C10 -53.5(3) . . . . ?
N5 C10 C16 N2 52.9(3) . . . . ?
C9 C7 C17 O8 1.9(4) . . . . ?
C8 C7 C17 O8 179.6(2) . . . . ?
C9 C7 C17 O6 -177.5(2) . . . . ?
C8 C7 C17 O6 0.2(4) . . . . ?
C22 C19 C20 O5 177.7(3) . . . . ?
C22 C19 C20 C1 -3.0(4) . . . . ?
O4 C1 C20 O5 1.6(3) . . . . ?
C5 C1 C20 O5 -178.8(2) . . . . ?
O4 C1 C20 C19 -177.6(2) . . . . ?
C5 C1 C20 C19 2.0(4) . . . . ?
C20 C19 C22 C15 1.6(5) . . . . ?
C5 C15 C22 C19 0.9(5) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2086229'
loop_
_audit_author_name
_audit_author_address
'Yu Duan'
;Jiamusi University
China
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;
_audit_creation_date             2021-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N5 O3, C7 H5 O3, C7 H6 O3, 2(H2 O)'
_chemical_formula_sum            'C28 H33 N5 O11'
_chemical_formula_weight         615.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0857(7)
_cell_length_b                   12.8969(12)
_cell_length_c                   15.2536(13)
_cell_angle_alpha                106.133(8)
_cell_angle_beta                 103.719(7)
_cell_angle_gamma                96.363(7)
_cell_volume                     1457.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2789
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.1420
_cell_measurement_theta_min      4.1350
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11385
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.533
_diffrn_reflns_theta_min         3.535
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4165
_reflns_number_total             6655
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.028
_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)+(0.0456P)²+0.2682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O10(H10A,H10B), O11(H11A,H11B)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C17(H17), C18(H18), C19(H19), C24(H24), C26(H26), C27(H27),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_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
O1 O 0.0946(2) 0.77390(13) 0.20894(12) 0.0524(5) Uani 1 1 d . . . . .
O2 O -0.1234(2) 0.68796(14) 0.08161(13) 0.0577(5) Uani 1 1 d . . . . .
H2 H -0.172668 0.624576 0.050998 0.086 Uiso 1 1 calc GR . . . .
O3 O -0.1949(2) 0.48333(13) 0.02080(11) 0.0481(4) Uani 1 1 d . . . . .
N1 N -0.0620(2) -0.03795(14) 0.26156(12) 0.0353(4) Uani 1 1 d . . . . .
H1A H 0.004737 -0.088257 0.253436 0.042 Uiso 1 1 calc R . . . .
H1B H -0.128820 -0.054181 0.296453 0.042 Uiso 1 1 calc R . . . .
N2 N 0.0456(2) 0.09991(14) 0.16300(13) 0.0385(5) Uani 1 1 d . . . . .
N3 N -0.1155(2) 0.18429(14) 0.06628(12) 0.0386(5) Uani 1 1 d . . . . .
N4 N 0.1050(2) 0.28827(14) 0.21085(12) 0.0324(4) Uani 1 1 d . . . . .
N5 N 0.1666(2) 0.47853(14) 0.25824(12) 0.0321(4) Uani 1 1 d . . . . .
C1 C -0.1736(3) -0.04259(18) 0.16731(16) 0.0396(6) Uani 1 1 d . . . . .
H1C H -0.255884 0.005991 0.175928 0.047 Uiso 1 1 calc R . . . .
H1D H -0.238216 -0.116795 0.133811 0.047 Uiso 1 1 calc R . . . .
C2 C -0.0627(3) -0.00819(17) 0.10950(16) 0.0406(6) Uani 1 1 d . . . . .
H2A H 0.010180 -0.061640 0.094591 0.049 Uiso 1 1 calc R . . . .
H2B H -0.136361 -0.005518 0.050174 0.049 Uiso 1 1 calc R . . . .
C3 C 0.0499(3) 0.07234(18) 0.31351(16) 0.0414(6) Uani 1 1 d . . . . .
H3A H 0.124310 0.071466 0.373302 0.050 Uiso 1 1 calc R . . . .
H3B H -0.021690 0.126941 0.327260 0.050 Uiso 1 1 calc R . . . .
C4 C 0.1587(3) 0.10135(19) 0.25308(17) 0.0424(6) Uani 1 1 d . . . . .
H4A H 0.230339 0.173802 0.285683 0.051 Uiso 1 1 calc R . . . .
H4B H 0.234434 0.048748 0.241916 0.051 Uiso 1 1 calc R . . . .
C5 C 0.0119(3) 0.19390(17) 0.14698(15) 0.0328(5) Uani 1 1 d . . . . .
C6 C -0.1414(3) 0.27709(18) 0.05086(15) 0.0381(5) Uani 1 1 d . . . . .
H6 H -0.225794 0.273648 -0.003747 0.046 Uiso 1 1 calc R . . . .
C7 C -0.0506(3) 0.38058(17) 0.11099(14) 0.0309(5) Uani 1 1 d . . . . .
C8 C 0.0726(3) 0.37993(16) 0.19222(14) 0.0288(5) Uani 1 1 d . . . . .
C9 C 0.1390(3) 0.57341(17) 0.24212(15) 0.0332(5) Uani 1 1 d . . . . .
H9 H 0.204335 0.638725 0.286826 0.040 Uiso 1 1 calc R . . . .
C10 C 0.0216(3) 0.57971(17) 0.16455(14) 0.0317(5) Uani 1 1 d . . . . .
C11 C -0.0826(3) 0.48109(17) 0.09336(15) 0.0334(5) Uani 1 1 d . . . . .
C12 C 0.0020(3) 0.68772(18) 0.15397(17) 0.0395(5) Uani 1 1 d . . . . .
C13 C 0.2958(3) 0.47928(19) 0.34571(16) 0.0400(6) Uani 1 1 d . . . . .
H13A H 0.377558 0.548569 0.370955 0.048 Uiso 1 1 calc R . . . .
H13B H 0.359918 0.420841 0.329711 0.048 Uiso 1 1 calc R . . . .
C14 C 0.2128(3) 0.4642(2) 0.42073(17) 0.0520(7) Uani 1 1 d . . . . .
H14A H 0.135915 0.394082 0.397150 0.078 Uiso 1 1 calc GR . . . .
H14B H 0.148513 0.521520 0.436503 0.078 Uiso 1 1 calc GR . . . .
H14C H 0.301101 0.467184 0.476493 0.078 Uiso 1 1 calc GR . . . .
O4 O 0.85519(18) 0.08965(14) 0.57304(13) 0.0489(4) Uani 1 1 d . . . . .
H4 H 0.942144 0.118675 0.563796 0.073 Uiso 1 1 calc GR . . . .
O5 O 0.29296(19) 0.09997(15) 0.65107(12) 0.0512(5) Uani 1 1 d . . . . .
O6 O 0.14563(17) 0.18123(13) 0.55580(12) 0.0438(4) Uani 1 1 d . . . . .
C15 C 0.2805(3) 0.14793(18) 0.58951(15) 0.0339(5) Uani 1 1 d . . . . .
C16 C 0.4346(2) 0.16780(16) 0.55368(14) 0.0290(5) Uani 1 1 d . . . . .
C17 C 0.4357(3) 0.23312(18) 0.49492(15) 0.0359(5) Uani 1 1 d . . . . .
H17 H 0.340850 0.265425 0.477958 0.043 Uiso 1 1 calc R . . . .
C18 C 0.5778(3) 0.24974(19) 0.46196(16) 0.0427(6) Uani 1 1 d . . . . .
H18 H 0.577691 0.292843 0.422155 0.051 Uiso 1 1 calc R . . . .
C19 C 0.7200(3) 0.20350(19) 0.48707(16) 0.0385(5) Uani 1 1 d . . . . .
H19 H 0.815197 0.215407 0.464380 0.046 Uiso 1 1 calc R . . . .
C20 C 0.7209(2) 0.13926(17) 0.54617(15) 0.0317(5) Uani 1 1 d . . . . .
C21 C 0.5776(3) 0.12143(18) 0.57887(15) 0.0322(5) Uani 1 1 d . . . . .
H21 H 0.577(2) 0.0716(17) 0.6155(14) 0.033(6) Uiso 1 1 d . . . . .
O7 O -0.5525(3) 0.18112(17) 0.11507(16) 0.0772(7) Uani 1 1 d . . . . .
H7 H -0.555(5) 0.101(4) 0.109(3) 0.131(14) Uiso 1 1 d . . . . .
O8 O -0.3295(3) 0.19727(15) 0.23818(14) 0.0710(6) Uani 1 1 d . . . . .
O9 O -0.1309(2) 0.60353(16) 0.38814(13) 0.0580(5) Uani 1 1 d . . . . .
H9A H -0.137(4) 0.675(3) 0.400(2) 0.106(13) Uiso 1 1 d . . . . .
C22 C -0.4231(3) 0.2386(2) 0.18984(19) 0.0482(6) Uani 1 1 d . . . . .
C23 C -0.4035(3) 0.35943(19) 0.20734(17) 0.0418(6) Uani 1 1 d . . . . .
C24 C -0.2801(3) 0.42771(19) 0.28844(16) 0.0404(5) Uani 1 1 d . . . . .
H24 H -0.213411 0.397654 0.330081 0.048 Uiso 1 1 calc R . . . .
C25 C -0.2556(3) 0.54051(19) 0.30773(17) 0.0405(6) Uani 1 1 d . . . . .
C26 C -0.3543(3) 0.5846(2) 0.24505(18) 0.0461(6) Uani 1 1 d . . . . .
H26 H -0.337654 0.660361 0.257236 0.055 Uiso 1 1 calc R . . . .
C27 C -0.4775(3) 0.5160(2) 0.16441(18) 0.0533(7) Uani 1 1 d . . . . .
H27 H -0.544002 0.545956 0.122612 0.064 Uiso 1 1 calc R . . . .
C28 C -0.5027(3) 0.4037(2) 0.14531(18) 0.0512(7) Uani 1 1 d . . . . .
H28 H -0.586050 0.357952 0.090950 0.061 Uiso 1 1 calc R . . . .
O10 O -0.4020(3) 0.03007(16) -0.08080(16) 0.0830(7) Uani 1 1 d . . . . .
H10A H -0.320529 0.068852 -0.032196 0.124 Uiso 1 1 d G . . . .
H10B H -0.410892 0.067875 -0.118717 0.124 Uiso 1 1 d G . . . .
O11 O -0.4288(3) 0.1639(3) -0.18928(15) 0.0979(9) Uani 1 1 d . . . . .
H11A H -0.339450 0.184507 -0.204798 0.147 Uiso 1 1 d G . . . .
H11B H -0.511141 0.146348 -0.240254 0.147 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.224(3) . ?
O2 H2 0.8200 . ?
O2 C12 1.311(3) . ?
O3 C11 1.264(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.486(3) . ?
N1 C3 1.489(3) . ?
N2 C2 1.461(3) . ?
N2 C4 1.453(3) . ?
N2 C5 1.345(3) . ?
N3 C5 1.370(3) . ?
N3 C6 1.312(3) . ?
N4 C5 1.337(2) . ?
N4 C8 1.329(3) . ?
N5 C8 1.386(2) . ?
N5 C9 1.345(3) . ?
N5 C13 1.484(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.511(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.506(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.394(3) . ?
C7 C8 1.396(3) . ?
C7 C11 1.433(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.358(3) . ?
C10 C11 1.438(3) . ?
C10 C12 1.468(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.502(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 H4 0.8200 . ?
O4 C20 1.358(2) . ?
O5 C15 1.251(3) . ?
O6 C15 1.264(2) . ?
C15 C16 1.500(3) . ?
C16 C17 1.391(3) . ?
C16 C21 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(3) . ?
C20 C21 1.386(3) . ?
C21 H21 0.96(2) . ?
O7 H7 1.01(4) . ?
O7 C22 1.318(3) . ?
O8 C22 1.202(3) . ?
O9 H9A 0.90(4) . ?
O9 C25 1.364(3) . ?
C22 C23 1.489(3) . ?
C23 C24 1.384(3) . ?
C23 C28 1.381(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(3) . ?
C25 C26 1.384(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.377(4) . ?
C28 H28 0.9300 . ?
O10 H10A 0.8504 . ?
O10 H10B 0.8498 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8499 . ?

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
C12 O2 H2 109.5 . . ?
H1A N1 H1B 107.9 . . ?
C1 N1 H1A 109.2 . . ?
C1 N1 H1B 109.2 . . ?
C1 N1 C3 112.10(16) . . ?
C3 N1 H1A 109.2 . . ?
C3 N1 H1B 109.2 . . ?
C4 N2 C2 112.32(17) . . ?
C5 N2 C2 124.04(19) . . ?
C5 N2 C4 120.93(18) . . ?
C6 N3 C5 115.49(18) . . ?
C8 N4 C5 116.35(18) . . ?
C8 N5 C13 120.32(17) . . ?
C9 N5 C8 119.20(18) . . ?
C9 N5 C13 120.48(17) . . ?
N1 C1 H1C 109.7 . . ?
N1 C1 H1D 109.7 . . ?
N1 C1 C2 109.85(17) . . ?
H1C C1 H1D 108.2 . . ?
C2 C1 H1C 109.7 . . ?
C2 C1 H1D 109.7 . . ?
N2 C2 C1 109.94(18) . . ?
N2 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
N1 C3 C4 109.17(18) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
N2 C4 C3 109.18(18) . . ?
N2 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 N3 116.85(19) . . ?
N4 C5 N2 117.45(19) . . ?
N4 C5 N3 125.7(2) . . ?
N3 C6 H6 117.9 . . ?
N3 C6 C7 124.3(2) . . ?
C7 C6 H6 117.9 . . ?
C6 C7 C8 114.91(19) . . ?
C6 C7 C11 123.34(19) . . ?
C8 C7 C11 121.73(18) . . ?
N4 C8 N5 117.09(18) . . ?
N4 C8 C7 123.24(18) . . ?
N5 C8 C7 119.67(19) . . ?
N5 C9 H9 118.0 . . ?
N5 C9 C10 124.04(19) . . ?
C10 C9 H9 118.0 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 C12 119.56(19) . . ?
C11 C10 C12 120.3(2) . . ?
O3 C11 C7 122.62(19) . . ?
O3 C11 C10 122.2(2) . . ?
C7 C11 C10 115.22(19) . . ?
O1 C12 O2 120.7(2) . . ?
O1 C12 C10 123.2(2) . . ?
O2 C12 C10 116.1(2) . . ?
N5 C13 H13A 109.1 . . ?
N5 C13 H13B 109.1 . . ?
N5 C13 C14 112.30(18) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 O4 H4 109.5 . . ?
O5 C15 O6 124.0(2) . . ?
O5 C15 C16 118.26(19) . . ?
O6 C15 C16 117.8(2) . . ?
C17 C16 C15 120.45(19) . . ?
C21 C16 C15 120.30(19) . . ?
C21 C16 C17 119.25(19) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
O4 C20 C19 123.21(18) . . ?
O4 C20 C21 117.23(19) . . ?
C19 C20 C21 119.5(2) . . ?
C16 C21 C20 120.8(2) . . ?
C16 C21 H21 121.0(12) . . ?
C20 C21 H21 118.1(12) . . ?
C22 O7 H7 107(2) . . ?
C25 O9 H9A 111(2) . . ?
O7 C22 C23 113.2(2) . . ?
O8 C22 O7 123.2(2) . . ?
O8 C22 C23 123.6(2) . . ?
C24 C23 C22 117.8(2) . . ?
C28 C23 C22 122.1(2) . . ?
C28 C23 C24 120.1(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
O9 C25 C24 117.6(2) . . ?
O9 C25 C26 122.9(2) . . ?
C24 C25 C26 119.6(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 H28 120.2 . . ?
C27 C28 C23 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
H10A O10 H10B 104.5 . . ?
H11A O11 H11B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -54.7(2) . . . . ?
N1 C3 C4 N2 58.2(2) . . . . ?
N3 C6 C7 C8 -0.8(3) . . . . ?
N3 C6 C7 C11 -179.2(2) . . . . ?
N5 C9 C10 C11 0.0(3) . . . . ?
N5 C9 C10 C12 -179.99(19) . . . . ?
C1 N1 C3 C4 -57.0(2) . . . . ?
C2 N2 C4 C3 -60.9(2) . . . . ?
C2 N2 C5 N3 -10.7(3) . . . . ?
C2 N2 C5 N4 169.28(19) . . . . ?
C3 N1 C1 C2 55.3(2) . . . . ?
C4 N2 C2 C1 59.1(2) . . . . ?
C4 N2 C5 N3 -170.57(19) . . . . ?
C4 N2 C5 N4 9.4(3) . . . . ?
C5 N2 C2 C1 -102.3(2) . . . . ?
C5 N2 C4 C3 101.2(2) . . . . ?
C5 N3 C6 C7 -0.9(3) . . . . ?
C5 N4 C8 N5 179.27(17) . . . . ?
C5 N4 C8 C7 -0.2(3) . . . . ?
C6 N3 C5 N2 -177.78(19) . . . . ?
C6 N3 C5 N4 2.3(3) . . . . ?
C6 C7 C8 N4 1.3(3) . . . . ?
C6 C7 C8 N5 -178.09(18) . . . . ?
C6 C7 C11 O3 -0.9(3) . . . . ?
C6 C7 C11 C10 178.7(2) . . . . ?
C8 N4 C5 N2 178.28(18) . . . . ?
C8 N4 C5 N3 -1.7(3) . . . . ?
C8 N5 C9 C10 0.8(3) . . . . ?
C8 N5 C13 C14 -80.0(2) . . . . ?
C8 C7 C11 O3 -179.2(2) . . . . ?
C8 C7 C11 C10 0.4(3) . . . . ?
C9 N5 C8 N4 179.58(18) . . . . ?
C9 N5 C8 C7 -0.9(3) . . . . ?
C9 N5 C13 C14 99.9(2) . . . . ?
C9 C10 C11 O3 179.0(2) . . . . ?
C9 C10 C11 C7 -0.6(3) . . . . ?
C9 C10 C12 O1 4.9(3) . . . . ?
C9 C10 C12 O2 -174.5(2) . . . . ?
C11 C7 C8 N4 179.76(19) . . . . ?
C11 C7 C8 N5 0.3(3) . . . . ?
C11 C10 C12 O1 -175.1(2) . . . . ?
C11 C10 C12 O2 5.5(3) . . . . ?
C12 C10 C11 O3 -1.0(3) . . . . ?
C12 C10 C11 C7 179.38(19) . . . . ?
C13 N5 C8 N4 -0.5(3) . . . . ?
C13 N5 C8 C7 178.94(19) . . . . ?
C13 N5 C9 C10 -179.09(19) . . . . ?
O4 C20 C21 C16 -179.13(19) . . . . ?
O5 C15 C16 C17 -171.5(2) . . . . ?
O5 C15 C16 C21 8.4(3) . . . . ?
O6 C15 C16 C17 8.2(3) . . . . ?
O6 C15 C16 C21 -171.91(19) . . . . ?
C15 C16 C17 C18 -179.44(19) . . . . ?
C15 C16 C21 C20 -179.99(19) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 O4 179.1(2) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
O7 C22 C23 C24 175.0(2) . . . . ?
O7 C22 C23 C28 -5.5(3) . . . . ?
O8 C22 C23 C24 -5.8(4) . . . . ?
O8 C22 C23 C28 173.7(3) . . . . ?
O9 C25 C26 C27 179.4(2) . . . . ?
C22 C23 C24 C25 179.5(2) . . . . ?
C22 C23 C28 C27 -179.2(2) . . . . ?
C23 C24 C25 O9 -179.3(2) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C23 C28 C27 0.3(4) . . . . ?
C24 C25 C26 C27 0.7(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C23 -0.2(4) . . . . ?
C28 C23 C24 C25 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
