# 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 2019

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1529858'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.	2019-06-10 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         'C22 H28 N O3, C6 H2 N3 O7'
_chemical_formula_sum            'C28 H30 N4 O10'
_chemical_formula_weight         582.56

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   22.0277(12)
_cell_length_b                   13.4965(7)
_cell_length_c                   21.8512(12)
_cell_angle_alpha                90
_cell_angle_beta                 118.2720(10)
_cell_angle_gamma                90
_cell_volume                     5721.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    9499
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.7

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27103
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5044
_reflns_number_gt                4264
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_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)+(0.1262P)²+5.3267P] 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         5044
_refine_ls_number_parameters     387
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.2063
_refine_ls_wR_factor_gt          0.1950
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.19401(11) 1.16417(13) 0.19293(11) 0.0673(6) Uani 1 1 d . . . . .
O2 O 0.61077(8) 0.67960(13) 0.61497(9) 0.0538(5) Uani 1 1 d . . . . .
O3 O 0.67533(11) 0.85837(17) 0.65736(12) 0.0854(8) Uani 1 1 d . . . . .
O4 O 0.67032(14) 0.9359(2) 0.57069(15) 0.1104(10) Uani 1 1 d . . . . .
O5 O 0.44682(12) 0.97115(16) 0.37123(11) 0.0770(7) Uani 1 1 d . . . . .
O6 O 0.36741(11) 0.86685(17) 0.35580(11) 0.0823(7) Uani 1 1 d . . . . .
O7 O 0.43111(15) 0.5621(2) 0.48522(15) 0.1207(12) Uani 1 1 d . . . . .
O8 O 0.49265(13) 0.5865(2) 0.59560(14) 0.1015(10) Uani 1 1 d . . . . .
O9 O 0.41152(16) 0.7148(2) 0.09178(16) 0.1028(9) Uani 1 1 d . . . . .
O10 O 0.10902(15) 0.7067(2) 0.42138(15) 0.0935(8) Uani 1 1 d . . . . .
N1 N 0.23372(9) 0.87813(14) 0.23150(9) 0.0359(4) Uani 1 1 d D . . . .
N2 N 0.64706(11) 0.87731(17) 0.59581(13) 0.0611(6) Uani 1 1 d . . . . .
N3 N 0.42674(11) 0.89689(16) 0.38806(11) 0.0538(6) Uani 1 1 d . . . . .
N4 N 0.47283(12) 0.60984(19) 0.53504(14) 0.0735(8) Uani 1 1 d . . . . .
C1 C 0.27080(11) 0.94086(16) 0.20216(11) 0.0391(5) Uani 1 1 d . . . . .
H1 H 0.3061 0.9793 0.2405 0.047 Uiso 1 1 calc R U . . .
C2 C 0.21831(12) 1.01483(18) 0.14983(12) 0.0463(6) Uani 1 1 d . . . . .
H2 H 0.1809 0.9768 0.1131 0.056 Uiso 1 1 calc R U . . .
C3 C 0.18841(12) 1.07448(18) 0.18789(12) 0.0462(6) Uani 1 1 d . . . . .
C4 C 0.15352(12) 1.01427(18) 0.22069(13) 0.0462(6) Uani 1 1 d . . . . .
H4 H 0.1159 0.9768 0.1838 0.055 Uiso 1 1 calc R U . . .
C5 C 0.20674(11) 0.93899(17) 0.27131(11) 0.0399(5) Uani 1 1 d . . . . .
H5 H 0.2455 0.9768 0.3066 0.048 Uiso 1 1 calc R U . . .
C6 C 0.30664(12) 0.87741(18) 0.17264(12) 0.0445(5) Uani 1 1 d . . . . .
C7 C 0.27209(14) 0.8054(2) 0.12367(14) 0.0547(6) Uani 1 1 d . . . . .
H7 H 0.2256 0.7944 0.1093 0.066 Uiso 1 1 calc R U . . .
C8 C 0.30527(18) 0.7486(2) 0.09532(16) 0.0671(8) Uani 1 1 d . . . . .
H8 H 0.2814 0.6993 0.0630 0.081 Uiso 1 1 calc R U . . .
C9 C 0.37410(18) 0.7662(2) 0.11562(17) 0.0689(8) Uani 1 1 d . . . . .
C10 C 0.40896(17) 0.8393(3) 0.16415(19) 0.0784(10) Uani 1 1 d . . . . .
H10 H 0.4551 0.8518 0.1775 0.094 Uiso 1 1 calc R U . . .
C11 C 0.37573(14) 0.8932(2) 0.19254(16) 0.0632(7) Uani 1 1 d . . . . .
H11 H 0.4000 0.9412 0.2258 0.076 Uiso 1 1 calc R U . . .
C12 C 0.25039(18) 1.0795(2) 0.11643(17) 0.0707(8) Uani 1 1 d . . . . .
H12A H 0.2686 1.0385 0.0930 0.106 Uiso 1 1 calc R U . . .
H12B H 0.2160 1.1231 0.0835 0.106 Uiso 1 1 calc R U . . .
H12C H 0.2870 1.1179 0.1516 0.106 Uiso 1 1 calc R U . . .
C13 C 0.12292(17) 1.0782(2) 0.25666(17) 0.0677(8) Uani 1 1 d . . . . .
H13A H 0.1111 1.0363 0.2855 0.081 Uiso 1 1 calc R U . . .
H13B H 0.1574 1.1253 0.2868 0.081 Uiso 1 1 calc R U . . .
C14 C 0.0607(3) 1.1327(4) 0.2070(3) 0.135(2) Uani 1 1 d . . . . .
H14A H 0.0434 1.1717 0.2321 0.203 Uiso 1 1 calc R U . . .
H14B H 0.0723 1.1753 0.1789 0.203 Uiso 1 1 calc R U . . .
H14C H 0.0261 1.0863 0.1776 0.203 Uiso 1 1 calc R U . . .
C15 C 0.17953(12) 0.87305(18) 0.30847(12) 0.0448(5) Uani 1 1 d . . . . .
C16 C 0.21028(16) 0.8759(2) 0.38041(14) 0.0602(7) Uani 1 1 d . . . . .
H16 H 0.2485 0.9163 0.4048 0.072 Uiso 1 1 calc R U . . .
C17 C 0.18559(19) 0.8205(3) 0.41607(16) 0.0733(9) Uani 1 1 d . . . . .
H17 H 0.2069 0.8239 0.4643 0.088 Uiso 1 1 calc R U . . .
C18 C 0.12972(16) 0.7601(2) 0.38137(17) 0.0639(8) Uani 1 1 d . . . . .
C19 C 0.09957(16) 0.7537(3) 0.31059(18) 0.0768(9) Uani 1 1 d . . . . .
H19 H 0.0626 0.7109 0.2868 0.092 Uiso 1 1 calc R U . . .
C20 C 0.12423(15) 0.8111(3) 0.27422(15) 0.0682(8) Uani 1 1 d . . . . .
H20 H 0.1029 0.8075 0.2260 0.082 Uiso 1 1 calc R U . . .
C21 C 0.56778(11) 0.73281(17) 0.56773(11) 0.0410(5) Uani 1 1 d . . . . .
C22 C 0.58199(11) 0.82966(17) 0.54973(12) 0.0426(5) Uani 1 1 d . . . . .
C23 C 0.53822(12) 0.88106(17) 0.49151(12) 0.0448(5) Uani 1 1 d . . . . .
H23 H 0.5516 0.9412 0.4809 0.054 Uiso 1 1 calc R U . . .
C24 C 0.47368(11) 0.84223(17) 0.44869(11) 0.0419(5) Uani 1 1 d . . . . .
C25 C 0.45327(11) 0.75321(17) 0.46330(12) 0.0455(6) Uani 1 1 d . . . . .
H25 H 0.4095 0.7282 0.4344 0.055 Uiso 1 1 calc R U . . .
C26 C 0.49825(12) 0.70176(17) 0.52113(12) 0.0451(6) Uani 1 1 d . . . . .
C27 C 0.3839(3) 0.6255(3) 0.0554(2) 0.1079(15) Uani 1 1 d . . . . .
H27A H 0.4156 0.5972 0.0416 0.162 Uiso 1 1 calc R U . . .
H27B H 0.3766 0.5799 0.0850 0.162 Uiso 1 1 calc R U . . .
H27C H 0.3408 0.6388 0.0149 0.162 Uiso 1 1 calc R U . . .
C28 C 0.0574(3) 0.6361(3) 0.3898(3) 0.1153(17) Uani 1 1 d . . . . .
H28A H 0.0486 0.6050 0.4243 0.173 Uiso 1 1 calc R U . . .
H28B H 0.0162 0.6676 0.3556 0.173 Uiso 1 1 calc R U . . .
H28C H 0.0720 0.5870 0.3677 0.173 Uiso 1 1 calc R U . . .
H1N H 0.2004(8) 0.8493(15) 0.2004(9) 0.032(6) Uiso 1 1 d D . . . .
H2N H 0.2602(10) 0.8346(14) 0.2570(11) 0.042(7) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.217(3) . ?
O2 C21 1.246(3) . ?
O3 N2 1.212(3) . ?
O4 N2 1.206(3) . ?
O5 N3 1.220(3) . ?
O6 N3 1.223(3) . ?
O7 N4 1.224(4) . ?
O8 N4 1.222(3) . ?
O9 C9 1.356(4) . ?
O9 C27 1.413(6) . ?
O10 C18 1.367(3) . ?
O10 C28 1.390(5) . ?
N1 C5 1.508(3) . ?
N1 C1 1.514(3) . ?
N1 H1N 0.825(10) . ?
N1 H2N 0.829(10) . ?
N2 C22 1.454(3) . ?
N3 C24 1.439(3) . ?
N4 C26 1.451(3) . ?
C1 C6 1.502(3) . ?
C1 C2 1.545(3) . ?
C1 H1 0.9800 . ?
C2 C12 1.511(4) . ?
C2 C3 1.514(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.512(4) . ?
C4 C13 1.522(4) . ?
C4 C5 1.550(3) . ?
C4 H4 0.9800 . ?
C5 C15 1.507(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.378(4) . ?
C6 C11 1.387(4) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(5) . ?
C10 C11 1.371(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.479(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.371(4) . ?
C15 C16 1.387(4) . ?
C16 C17 1.365(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(5) . ?
C19 C20 1.392(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.441(3) . ?
C21 C26 1.442(3) . ?
C22 C23 1.367(3) . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(3) . ?
C25 C26 1.369(3) . ?
C25 H25 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
C9 O9 C27 118.3(3) . . ?
C18 O10 C28 119.1(3) . . ?
C5 N1 C1 112.26(17) . . ?
C5 N1 H1N 107.0(16) . . ?
C1 N1 H1N 111.3(16) . . ?
C5 N1 H2N 110.0(17) . . ?
C1 N1 H2N 109.4(17) . . ?
H1N N1 H2N 107(2) . . ?
O4 N2 O3 122.5(2) . . ?
O4 N2 C22 117.8(2) . . ?
O3 N2 C22 119.7(2) . . ?
O5 N3 O6 122.6(2) . . ?
O5 N3 C24 119.6(2) . . ?
O6 N3 C24 117.8(2) . . ?
O8 N4 O7 124.0(3) . . ?
O8 N4 C26 118.2(3) . . ?
O7 N4 C26 117.7(3) . . ?
C6 C1 N1 111.22(18) . . ?
C6 C1 C2 114.32(18) . . ?
N1 C1 C2 108.06(17) . . ?
C6 C1 H1 107.7 . . ?
N1 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
C12 C2 C3 112.5(2) . . ?
C12 C2 C1 111.9(2) . . ?
C3 C2 C1 107.74(18) . . ?
C12 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
O1 C3 C4 123.0(2) . . ?
O1 C3 C2 121.8(2) . . ?
C4 C3 C2 115.19(19) . . ?
C3 C4 C13 112.9(2) . . ?
C3 C4 C5 107.94(18) . . ?
C13 C4 C5 111.9(2) . . ?
C3 C4 H4 108.0 . . ?
C13 C4 H4 108.0 . . ?
C5 C4 H4 108.0 . . ?
C15 C5 N1 110.79(18) . . ?
C15 C5 C4 114.34(18) . . ?
N1 C5 C4 108.48(17) . . ?
C15 C5 H5 107.7 . . ?
N1 C5 H5 107.7 . . ?
C4 C5 H5 107.7 . . ?
C7 C6 C11 118.2(2) . . ?
C7 C6 C1 121.8(2) . . ?
C11 C6 C1 120.0(2) . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
O9 C9 C10 116.2(3) . . ?
O9 C9 C8 124.2(3) . . ?
C10 C9 C8 119.6(3) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C4 112.7(3) . . ?
C14 C13 H13A 109.1 . . ?
C4 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C4 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 117.8(2) . . ?
C20 C15 C5 122.9(2) . . ?
C16 C15 C5 119.3(2) . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 O10 124.0(3) . . ?
C17 C18 O10 116.4(3) . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 121.0(3) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
O2 C21 C22 124.8(2) . . ?
O2 C21 C26 123.6(2) . . ?
C22 C21 C26 111.47(19) . . ?
C23 C22 C21 124.4(2) . . ?
C23 C22 N2 116.7(2) . . ?
C21 C22 N2 118.8(2) . . ?
C22 C23 C24 118.9(2) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 121.3(2) . . ?
C25 C24 N3 119.4(2) . . ?
C23 C24 N3 119.3(2) . . ?
C26 C25 C24 119.0(2) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C21 124.5(2) . . ?
C25 C26 N4 116.4(2) . . ?
C21 C26 N4 119.1(2) . . ?
O9 C27 H27A 109.5 . . ?
O9 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O9 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O10 C28 H28A 109.5 . . ?
O10 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O10 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
C5 N1 C1 C6 171.06(17) . . . . ?
C5 N1 C1 C2 -62.7(2) . . . . ?
C6 C1 C2 C12 -54.3(3) . . . . ?
N1 C1 C2 C12 -178.7(2) . . . . ?
C6 C1 C2 C3 -178.51(19) . . . . ?
N1 C1 C2 C3 57.1(2) . . . . ?
C12 C2 C3 O1 -3.7(3) . . . . ?
C1 C2 C3 O1 120.2(2) . . . . ?
C12 C2 C3 C4 178.2(2) . . . . ?
C1 C2 C3 C4 -57.9(2) . . . . ?
O1 C3 C4 C13 3.3(3) . . . . ?
C2 C3 C4 C13 -178.6(2) . . . . ?
O1 C3 C4 C5 -120.9(2) . . . . ?
C2 C3 C4 C5 57.2(2) . . . . ?
C1 N1 C5 C15 -171.68(17) . . . . ?
C1 N1 C5 C4 62.0(2) . . . . ?
C3 C4 C5 C15 179.91(19) . . . . ?
C13 C4 C5 C15 55.1(3) . . . . ?
C3 C4 C5 N1 -55.9(2) . . . . ?
C13 C4 C5 N1 179.3(2) . . . . ?
N1 C1 C6 C7 53.9(3) . . . . ?
C2 C1 C6 C7 -68.8(3) . . . . ?
N1 C1 C6 C11 -128.6(2) . . . . ?
C2 C1 C6 C11 108.7(3) . . . . ?
C11 C6 C7 C8 0.9(4) . . . . ?
C1 C6 C7 C8 178.4(2) . . . . ?
C6 C7 C8 C9 -1.4(4) . . . . ?
C27 O9 C9 C10 165.4(3) . . . . ?
C27 O9 C9 C8 -13.6(5) . . . . ?
C7 C8 C9 O9 179.4(3) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
O9 C9 C10 C11 -178.2(3) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C6 -1.2(5) . . . . ?
C7 C6 C11 C10 0.4(4) . . . . ?
C1 C6 C11 C10 -177.1(3) . . . . ?
C3 C4 C13 C14 72.0(4) . . . . ?
C5 C4 C13 C14 -166.0(4) . . . . ?
N1 C5 C15 C20 -63.6(3) . . . . ?
C4 C5 C15 C20 59.3(3) . . . . ?
N1 C5 C15 C16 117.8(2) . . . . ?
C4 C5 C15 C16 -119.2(3) . . . . ?
C20 C15 C16 C17 -1.3(5) . . . . ?
C5 C15 C16 C17 177.3(3) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C19 1.5(5) . . . . ?
C16 C17 C18 O10 179.4(3) . . . . ?
C28 O10 C18 C19 4.7(5) . . . . ?
C28 O10 C18 C17 -173.0(4) . . . . ?
C17 C18 C19 C20 -2.4(5) . . . . ?
O10 C18 C19 C20 179.9(3) . . . . ?
C16 C15 C20 C19 0.5(5) . . . . ?
C5 C15 C20 C19 -178.1(3) . . . . ?
C18 C19 C20 C15 1.4(5) . . . . ?
O2 C21 C22 C23 169.3(2) . . . . ?
C26 C21 C22 C23 -6.9(3) . . . . ?
O2 C21 C22 N2 -10.6(4) . . . . ?
C26 C21 C22 N2 173.2(2) . . . . ?
O4 N2 C22 C23 -27.4(4) . . . . ?
O3 N2 C22 C23 151.6(3) . . . . ?
O4 N2 C22 C21 152.5(3) . . . . ?
O3 N2 C22 C21 -28.5(4) . . . . ?
C21 C22 C23 C24 4.8(4) . . . . ?
N2 C22 C23 C24 -175.3(2) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C22 C23 C24 N3 178.7(2) . . . . ?
O5 N3 C24 C25 -173.0(2) . . . . ?
O6 N3 C24 C25 7.8(4) . . . . ?
O5 N3 C24 C23 7.7(4) . . . . ?
O6 N3 C24 C23 -171.5(3) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
N3 C24 C25 C26 -179.9(2) . . . . ?
C24 C25 C26 C21 -2.2(4) . . . . ?
C24 C25 C26 N4 178.0(3) . . . . ?
O2 C21 C26 C25 -170.7(2) . . . . ?
C22 C21 C26 C25 5.6(4) . . . . ?
O2 C21 C26 N4 9.1(4) . . . . ?
C22 C21 C26 N4 -174.6(2) . . . . ?
O8 N4 C26 C25 -145.6(3) . . . . ?
O7 N4 C26 C25 32.2(4) . . . . ?
O8 N4 C26 C21 34.6(4) . . . . ?
O7 N4 C26 C21 -147.7(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
N1 H2N O6 0.83(1) 2.37(2) 2.915(3) 124(2) .
C14 H14B O1 0.96 2.55 3.122(7) 118 .
N1 H1N O2 0.83(1) 2.01(1) 2.809(2) 163(2) 8_465
C4 H4 O2 0.98 2.56 3.318(3) 134 8_465
C20 H20 O2 0.93 2.52 3.352(4) 149 8_465
N1 H2N O1 0.83(1) 2.54(1) 3.333(3) 160(2) 4_545
C16 H16 O4 0.93 2.56 3.443(4) 158 5_676
C27 H27A O7 0.96 2.58 3.370(5) 140 6_565

_refine_diff_density_max         1.099
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.058

