# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Form_I
_database_code_depnum_ccdc_archive 'CCDC 2001329'
loop_
_audit_author_name
_audit_author_address
'Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2020-07-30 downloaded from the CCDC.
;

_audit_creation_date             2020-07-13T11:13:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H9 O2, C6 H3 N3 O6, C5 H7 N2'
_chemical_formula_sum            'C26 H19 N5 O8'
_chemical_formula_weight         529.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   6.8892(2)
_cell_length_b                   13.9675(3)
_cell_length_c                   24.3771(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.5340(10)
_cell_angle_gamma                90
_cell_volume                     2341.22(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.24
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 2 0.042
0 -1 -2 0.023
-2 0 -1 0.176
2 0 1 0.179
0 1 -2 0.057
0 -1 2 0.059
1 0 -2 0.13

_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7159
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.99

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_number            46569
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.674
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             5639
_reflns_number_gt                4351
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
        Ortep for Windows (Farrugia, 2012)'
;
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.6419P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5639
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.67579(18) 0.33602(9) 0.31450(6) 0.0282(3) Uani 1 1 d . . . . .
C2 C 0.68833(18) 0.26525(10) 0.35407(6) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.724578 0.279146 0.391458 0.035 Uiso 1 1 calc R U . . .
C3 C 0.64549(18) 0.17319(10) 0.33654(6) 0.0301(3) Uani 1 1 d . . . . .
C4 C 0.59258(19) 0.15069(10) 0.28234(6) 0.0319(3) Uani 1 1 d . . . . .
H4A H 0.564856 0.086681 0.271248 0.038 Uiso 1 1 calc R U . . .
C5 C 0.58187(18) 0.22523(10) 0.24517(6) 0.0309(3) Uani 1 1 d . . . . .
C6 C 0.62343(18) 0.31912(10) 0.25988(6) 0.0302(3) Uani 1 1 d . . . . .
H6 H 0.616201 0.369422 0.233605 0.036 Uiso 1 1 calc R U . . .
N1 N 0.71890(16) 0.43533(8) 0.33153(5) 0.0316(3) Uani 1 1 d . . . . .
N2 N 0.65558(17) 0.09491(9) 0.37737(5) 0.0356(3) Uani 1 1 d . . . . .
N3 N 0.52197(18) 0.20427(10) 0.18738(5) 0.0396(3) Uani 1 1 d . . . . .
O1 O 0.66432(17) 0.49987(7) 0.30015(5) 0.0449(3) Uani 1 1 d . . . . .
O2 O 0.80646(14) 0.44750(7) 0.37597(4) 0.0384(2) Uani 1 1 d . . . . .
O3 O 0.69547(17) 0.11615(8) 0.42526(5) 0.0469(3) Uani 1 1 d . . . . .
O4 O 0.62478(18) 0.01365(8) 0.36074(5) 0.0534(3) Uani 1 1 d . . . . .
O5 O 0.45711(19) 0.12462(9) 0.17646(5) 0.0559(3) Uani 1 1 d . . . . .
O6 O 0.53766(18) 0.26887(9) 0.15383(5) 0.0526(3) Uani 1 1 d . . . . .
C7 C 0.19478(17) 0.27416(9) 0.37644(5) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.17536(18) 0.17951(10) 0.39563(5) 0.0287(3) Uani 1 1 d . . . . .
C9 C 0.2057(2) 0.15486(12) 0.45245(6) 0.0386(3) Uani 1 1 d . . . . .
H9 H 0.236587 0.203586 0.47874 0.046 Uiso 1 1 calc R U . . .
C10 C 0.1908(2) 0.06220(13) 0.46932(7) 0.0499(4) Uani 1 1 d . . . . .
H10 H 0.214354 0.047017 0.507135 0.06 Uiso 1 1 calc R U . . .
C11 C 0.1409(2) -0.01135(12) 0.43148(8) 0.0505(4) Uani 1 1 d . . . . .
H11 H 0.128417 -0.075226 0.444169 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1106(2) 0.00800(11) 0.37742(7) 0.0419(4) Uani 1 1 d . . . . .
H12 H 0.077757 -0.042502 0.352444 0.05 Uiso 1 1 calc R U . . .
C13 C 0.12749(18) 0.10389(9) 0.35718(6) 0.0308(3) Uani 1 1 d . . . . .
C14 C 0.09634(18) 0.12494(9) 0.30188(6) 0.0298(3) Uani 1 1 d . . . . .
H14 H 0.063252 0.074711 0.276744 0.036 Uiso 1 1 calc R U . . .
C15 C 0.11234(17) 0.21799(9) 0.28220(5) 0.0254(3) Uani 1 1 d . . . . .
C16 C 0.07939(19) 0.23883(11) 0.22501(6) 0.0322(3) Uani 1 1 d . . . . .
H16 H 0.045715 0.188506 0.199996 0.039 Uiso 1 1 calc R U . . .
C17 C 0.0955(2) 0.32935(11) 0.20601(6) 0.0352(3) Uani 1 1 d . . . . .
H17 H 0.074757 0.342142 0.167826 0.042 Uiso 1 1 calc R U . . .
C18 C 0.14326(19) 0.40483(10) 0.24303(6) 0.0324(3) Uani 1 1 d . . . . .
H18 H 0.15259 0.468194 0.229273 0.039 Uiso 1 1 calc R U . . .
C19 C 0.17617(18) 0.38898(9) 0.29786(5) 0.0264(3) Uani 1 1 d . . . . .
H19 H 0.207785 0.441223 0.321713 0.032 Uiso 1 1 calc R U . . .
C20 C 0.16369(17) 0.29432(9) 0.32005(5) 0.0227(3) Uani 1 1 d . . . . .
C21 C 0.25197(19) 0.35466(10) 0.41623(5) 0.0287(3) Uani 1 1 d . . . . .
O7 O 0.40317(14) 0.40099(7) 0.40686(4) 0.0377(2) Uani 1 1 d . . . . .
O8 O 0.14637(15) 0.36972(8) 0.45520(4) 0.0388(2) Uani 1 1 d . . . . .
C22 C 0.3070(2) 0.62400(12) 0.46754(6) 0.0393(3) Uani 1 1 d . . . . .
C23 C 0.3048(2) 0.72405(12) 0.47493(7) 0.0447(4) Uani 1 1 d . . . . .
H23 H 0.205527 0.752901 0.494677 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4445(2) 0.77932(12) 0.45385(7) 0.0434(4) Uani 1 1 d . . . . .
H24 H 0.442463 0.846718 0.45902 0.052 Uiso 1 1 calc R U . . .
C25 C 0.5914(2) 0.73767(12) 0.42457(6) 0.0417(4) Uani 1 1 d . . . . .
H25 H 0.689697 0.775972 0.409899 0.05 Uiso 1 1 calc R U . . .
C26 C 0.5899(2) 0.64129(12) 0.41768(6) 0.0389(3) Uani 1 1 d . . . . .
H26 H 0.688755 0.611872 0.398018 0.047 Uiso 1 1 calc R U . . .
N4 N 0.44918(18) 0.58603(10) 0.43844(5) 0.0364(3) Uani 1 1 d . . . . .
N5 N 0.1794(2) 0.56584(12) 0.48764(7) 0.0574(4) Uani 1 1 d . . . . .
H5A H 0.166(3) 0.4989(17) 0.4775(9) 0.075(6) Uiso 1 1 d . . . . .
H5B H 0.085(4) 0.5966(17) 0.5062(10) 0.084(7) Uiso 1 1 d . . . . .
H4 H 0.439(3) 0.5151(17) 0.4318(9) 0.076(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.3783(19) . ?
C1 C2 1.3801(19) . ?
C1 N1 1.4729(18) . ?
C2 C3 1.3813(19) . ?
C2 H2 0.95 . ?
C3 C4 1.385(2) . ?
C3 N2 1.4773(18) . ?
C4 C5 1.379(2) . ?
C4 H4A 0.95 . ?
C5 C6 1.385(2) . ?
C5 N3 1.4728(19) . ?
C6 H6 0.95 . ?
N1 O2 1.2190(15) . ?
N1 O1 1.2263(15) . ?
N2 O4 1.2194(16) . ?
N2 O3 1.2193(17) . ?
N3 O5 1.2221(17) . ?
N3 O6 1.2270(17) . ?
C7 C20 1.4065(18) . ?
C7 C8 1.4116(18) . ?
C7 C21 1.5209(18) . ?
C8 C9 1.430(2) . ?
C8 C13 1.437(2) . ?
C9 C10 1.364(2) . ?
C9 H9 0.95 . ?
C10 C11 1.409(3) . ?
C10 H10 0.95 . ?
C11 C12 1.349(3) . ?
C11 H11 0.95 . ?
C12 C13 1.4346(19) . ?
C12 H12 0.95 . ?
C13 C14 1.383(2) . ?
C14 C15 1.3920(19) . ?
C14 H14 0.95 . ?
C15 C16 1.4286(19) . ?
C15 C20 1.4397(18) . ?
C16 C17 1.353(2) . ?
C16 H16 0.95 . ?
C17 C18 1.413(2) . ?
C17 H17 0.95 . ?
C18 C19 1.3600(19) . ?
C18 H18 0.95 . ?
C19 C20 1.4331(17) . ?
C19 H19 0.95 . ?
C21 O8 1.2494(16) . ?
C21 O7 1.2591(17) . ?
C22 N5 1.314(2) . ?
C22 N4 1.3525(19) . ?
C22 C23 1.409(2) . ?
C23 C24 1.359(2) . ?
C23 H23 0.95 . ?
C24 C25 1.400(2) . ?
C24 H24 0.95 . ?
C25 C26 1.357(2) . ?
C25 H25 0.95 . ?
C26 N4 1.361(2) . ?
C26 H26 0.95 . ?
N4 H4 1.01(2) . ?
N5 H5A 0.97(2) . ?
N5 H5B 0.92(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 123.64(13) . . ?
C6 C1 N1 118.02(12) . . ?
C2 C1 N1 118.34(12) . . ?
C3 C2 C1 116.58(13) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C2 C3 C4 123.04(13) . . ?
C2 C3 N2 118.70(13) . . ?
C4 C3 N2 118.26(12) . . ?
C5 C4 C3 117.11(13) . . ?
C5 C4 H4A 121.4 . . ?
C3 C4 H4A 121.4 . . ?
C4 C5 C6 122.88(13) . . ?
C4 C5 N3 118.61(13) . . ?
C6 C5 N3 118.51(13) . . ?
C1 C6 C5 116.74(13) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O2 N1 O1 124.59(12) . . ?
O2 N1 C1 117.52(11) . . ?
O1 N1 C1 117.89(11) . . ?
O4 N2 O3 124.69(13) . . ?
O4 N2 C3 117.70(13) . . ?
O3 N2 C3 117.61(12) . . ?
O5 N3 O6 124.77(14) . . ?
O5 N3 C5 117.81(13) . . ?
O6 N3 C5 117.41(13) . . ?
C20 C7 C8 119.97(12) . . ?
C20 C7 C21 119.55(11) . . ?
C8 C7 C21 120.47(12) . . ?
C7 C8 C9 122.36(13) . . ?
C7 C8 C13 119.66(12) . . ?
C9 C8 C13 117.96(13) . . ?
C10 C9 C8 120.75(16) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.94(15) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.70(15) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.81(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 121.51(14) . . ?
C14 C13 C8 119.67(12) . . ?
C12 C13 C8 118.82(14) . . ?
C13 C14 C15 121.56(12) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 121.02(12) . . ?
C14 C15 C20 119.48(12) . . ?
C16 C15 C20 119.50(12) . . ?
C17 C16 C15 120.86(13) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.94(13) . . ?
C16 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C19 C18 C17 121.61(13) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 120.73(12) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C7 C20 C19 122.99(11) . . ?
C7 C20 C15 119.65(11) . . ?
C19 C20 C15 117.35(11) . . ?
O8 C21 O7 125.34(13) . . ?
O8 C21 C7 117.99(12) . . ?
O7 C21 C7 116.67(11) . . ?
N5 C22 N4 118.43(15) . . ?
N5 C22 C23 123.55(15) . . ?
N4 C22 C23 118.03(15) . . ?
C24 C23 C22 120.10(15) . . ?
C24 C23 H23 120 . . ?
C22 C23 H23 120 . . ?
C23 C24 C25 120.50(15) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 118.37(15) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C25 C26 N4 121.12(14) . . ?
C25 C26 H26 119.4 . . ?
N4 C26 H26 119.4 . . ?
C22 N4 C26 121.87(14) . . ?
C22 N4 H4 115.2(13) . . ?
C26 N4 H4 122.9(12) . . ?
C22 N5 H5A 123.8(13) . . ?
C22 N5 H5B 113.9(15) . . ?
H5A N5 H5B 121(2) . . ?

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
C6 C1 C2 C3 0.14(19) . . . . ?
N1 C1 C2 C3 179.56(11) . . . . ?
C1 C2 C3 C4 0.11(19) . . . . ?
C1 C2 C3 N2 -179.62(11) . . . . ?
C2 C3 C4 C5 -0.53(19) . . . . ?
N2 C3 C4 C5 179.20(11) . . . . ?
C3 C4 C5 C6 0.74(19) . . . . ?
C3 C4 C5 N3 -178.71(11) . . . . ?
C2 C1 C6 C5 0.04(19) . . . . ?
N1 C1 C6 C5 -179.37(11) . . . . ?
C4 C5 C6 C1 -0.50(19) . . . . ?
N3 C5 C6 C1 178.95(11) . . . . ?
C6 C1 N1 O2 -163.63(12) . . . . ?
C2 C1 N1 O2 16.93(17) . . . . ?
C6 C1 N1 O1 16.41(17) . . . . ?
C2 C1 N1 O1 -163.03(12) . . . . ?
C2 C3 N2 O4 -177.15(12) . . . . ?
C4 C3 N2 O4 3.10(18) . . . . ?
C2 C3 N2 O3 2.34(18) . . . . ?
C4 C3 N2 O3 -177.41(12) . . . . ?
C4 C5 N3 O5 10.55(18) . . . . ?
C6 C5 N3 O5 -168.93(13) . . . . ?
C4 C5 N3 O6 -170.76(12) . . . . ?
C6 C5 N3 O6 9.77(18) . . . . ?
C20 C7 C8 C9 179.85(11) . . . . ?
C21 C7 C8 C9 0.69(18) . . . . ?
C20 C7 C8 C13 1.20(17) . . . . ?
C21 C7 C8 C13 -177.95(11) . . . . ?
C7 C8 C9 C10 -178.22(13) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
C8 C9 C10 C11 -1.4(2) . . . . ?
C9 C10 C11 C12 1.4(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C14 -179.80(13) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
C7 C8 C13 C14 -1.54(18) . . . . ?
C9 C8 C13 C14 179.76(12) . . . . ?
C7 C8 C13 C12 179.28(12) . . . . ?
C9 C8 C13 C12 0.57(18) . . . . ?
C12 C13 C14 C15 179.89(12) . . . . ?
C8 C13 C14 C15 0.73(19) . . . . ?
C13 C14 C15 C16 -179.86(12) . . . . ?
C13 C14 C15 C20 0.40(18) . . . . ?
C14 C15 C16 C17 -179.85(12) . . . . ?
C20 C15 C16 C17 -0.11(19) . . . . ?
C15 C16 C17 C18 -0.8(2) . . . . ?
C16 C17 C18 C19 0.8(2) . . . . ?
C17 C18 C19 C20 0.10(19) . . . . ?
C8 C7 C20 C19 178.42(11) . . . . ?
C21 C7 C20 C19 -2.42(17) . . . . ?
C8 C7 C20 C15 -0.07(17) . . . . ?
C21 C7 C20 C15 179.09(10) . . . . ?
C18 C19 C20 C7 -179.47(12) . . . . ?
C18 C19 C20 C15 -0.94(17) . . . . ?
C14 C15 C20 C7 -0.74(17) . . . . ?
C16 C15 C20 C7 179.52(11) . . . . ?
C14 C15 C20 C19 -179.32(11) . . . . ?
C16 C15 C20 C19 0.94(17) . . . . ?
C20 C7 C21 O8 122.88(13) . . . . ?
C8 C7 C21 O8 -57.96(16) . . . . ?
C20 C7 C21 O7 -56.97(16) . . . . ?
C8 C7 C21 O7 122.19(14) . . . . ?
N5 C22 C23 C24 178.57(17) . . . . ?
N4 C22 C23 C24 -1.0(2) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C23 C24 C25 C26 0.3(2) . . . . ?
C24 C25 C26 N4 0.2(2) . . . . ?
N5 C22 N4 C26 -178.08(15) . . . . ?
C23 C22 N4 C26 1.5(2) . . . . ?
C25 C26 N4 C22 -1.1(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
N5 H5A O8 0.97(2) 1.89(2) 2.8563(19) 178(2) . yes
N5 H5B O8 0.92(3) 1.96(3) 2.8588(18) 166(2) 3_566 yes
N4 H4 O7 1.01(2) 1.72(2) 2.7098(16) 168(2) . yes

####################################################################### 
# 
# 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_Form_III
_database_code_depnum_ccdc_archive 'CCDC 2001331'
loop_
_audit_author_name
_audit_author_address
'Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-07-30 downloaded from the CCDC.
;

_audit_creation_date             2020-03-30T08:09:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H9 O2, C6 H3 N3 O6, C5 H7 N2'
_chemical_formula_sum            'C26 H19 N5 O8'
_chemical_formula_weight         529.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0834(5)
_cell_length_b                   12.8271(9)
_cell_length_c                   13.8555(9)
_cell_angle_alpha                77.196(2)
_cell_angle_beta                 85.946(2)
_cell_angle_gamma                81.281(2)
_cell_volume                     1212.51(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9292
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      28.2
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange-yellow
_exptl_crystal_size_max          0.895
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.45
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7116
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.987

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.02
_diffrn_reflns_number            40646
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             5832
_reflns_number_gt                4854
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
        Ortep for Windows (Farrugia, 2012)'
;
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.4958P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5832
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.72773(17) 0.41874(10) 0.26059(10) 0.0269(3) Uani 1 1 d . . . . .
C2 C 0.68581(18) 0.41523(11) 0.36008(10) 0.0287(3) Uani 1 1 d . . . . .
H2 H 0.64086 0.47876 0.384078 0.034 Uiso 1 1 calc R U . . .
C3 C 0.71253(18) 0.31473(11) 0.42288(9) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.78206(17) 0.22115(10) 0.39120(9) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.800578 0.153067 0.436064 0.03 Uiso 1 1 calc R U . . .
C5 C 0.82334(17) 0.23140(10) 0.29109(9) 0.0235(2) Uani 1 1 d . . . . .
C6 C 0.79480(17) 0.32870(10) 0.22310(10) 0.0254(3) Uani 1 1 d . . . . .
H6 H 0.820182 0.333111 0.154175 0.03 Uiso 1 1 calc R U . . .
N1 N 0.69805(17) 0.52386(10) 0.19020(10) 0.0374(3) Uani 1 1 d . . . . .
N2 N 0.90376(16) 0.13385(9) 0.25492(8) 0.0288(2) Uani 1 1 d . . . . .
N3 N 0.66539(17) 0.30571(10) 0.52936(9) 0.0346(3) Uani 1 1 d . . . . .
O1 O 0.68616(17) 0.52340(9) 0.10311(8) 0.0471(3) Uani 1 1 d . . . . .
O2 O 0.6870(2) 0.60486(9) 0.22417(11) 0.0564(3) Uani 1 1 d . . . . .
O3 O 0.6322(2) 0.38929(10) 0.55976(9) 0.0535(3) Uani 1 1 d . . . . .
O4 O 0.66326(18) 0.21543(10) 0.58114(8) 0.0467(3) Uani 1 1 d . . . . .
O5 O 0.91972(18) 0.04780(8) 0.31456(8) 0.0436(3) Uani 1 1 d . . . . .
O6 O 0.95159(17) 0.14443(9) 0.16738(8) 0.0428(3) Uani 1 1 d . . . . .
C7 C 0.30169(17) 0.29957(10) 0.25701(10) 0.0273(3) Uani 1 1 d . . . . .
C8 C 0.26329(19) 0.27583(12) 0.35986(11) 0.0355(3) Uani 1 1 d . . . . .
C9 C 0.1933(2) 0.35605(16) 0.41527(11) 0.0439(4) Uani 1 1 d . . . . .
H9 H 0.173524 0.429936 0.382424 0.053 Uiso 1 1 calc R U . . .
C10 C 0.1542(3) 0.3282(2) 0.51481(13) 0.0671(6) Uani 1 1 d . . . . .
H10 H 0.110084 0.382769 0.550738 0.081 Uiso 1 1 calc R U . . .
C11 C 0.1792(3) 0.2180(3) 0.56503(17) 0.0897(10) Uani 1 1 d . . . . .
H11 H 0.148524 0.19915 0.633977 0.108 Uiso 1 1 calc R U . . .
C12 C 0.2457(3) 0.1407(2) 0.51565(19) 0.0825(9) Uani 1 1 d . . . . .
H12 H 0.261978 0.067567 0.550701 0.099 Uiso 1 1 calc R U . . .
C13 C 0.2932(2) 0.16439(16) 0.41212(14) 0.0544(5) Uani 1 1 d . . . . .
C14 C 0.3660(3) 0.08453(14) 0.36073(19) 0.0643(7) Uani 1 1 d . . . . .
H13 H 0.383776 0.011324 0.395585 0.077 Uiso 1 1 calc R U . . .
C15 C 0.4133(2) 0.10828(12) 0.26070(18) 0.0537(5) Uani 1 1 d . . . . .
C16 C 0.4957(3) 0.02684(15) 0.2071(3) 0.0793(9) Uani 1 1 d . . . . .
H14 H 0.518914 -0.046324 0.241723 0.095 Uiso 1 1 calc R U . . .
C17 C 0.5403(3) 0.0516(2) 0.1098(3) 0.0860(10) Uani 1 1 d . . . . .
H15 H 0.592954 -0.003984 0.076367 0.103 Uiso 1 1 calc R U . . .
C18 C 0.5094(2) 0.15917(18) 0.0572(2) 0.0654(6) Uani 1 1 d . . . . .
H16 H 0.543204 0.175861 -0.011527 0.078 Uiso 1 1 calc R U . . .
C19 C 0.4318(2) 0.24006(14) 0.10320(14) 0.0433(4) Uani 1 1 d . . . . .
H17 H 0.412414 0.312293 0.066023 0.052 Uiso 1 1 calc R U . . .
C20 C 0.37907(19) 0.21819(11) 0.20619(13) 0.0358(3) Uani 1 1 d . . . . .
C21 C 0.25090(17) 0.41377(10) 0.19804(9) 0.0232(2) Uani 1 1 d . . . . .
O7 O 0.32338(13) 0.48686(7) 0.22379(7) 0.0308(2) Uani 1 1 d . . . . .
O8 O 0.13817(13) 0.42788(7) 0.12976(7) 0.0291(2) Uani 1 1 d . . . . .
C22 C 0.05663(17) 0.71733(10) 0.07666(9) 0.0223(2) Uani 1 1 d . . . . .
C23 C -0.03205(19) 0.82576(10) 0.05729(10) 0.0274(3) Uani 1 1 d . . . . .
H23 H -0.119 0.85127 0.005303 0.033 Uiso 1 1 calc R U . . .
C24 C 0.0083(2) 0.89362(11) 0.11393(10) 0.0317(3) Uani 1 1 d . . . . .
H24 H -0.0519 0.966461 0.101246 0.038 Uiso 1 1 calc R U . . .
C25 C 0.1373(2) 0.85729(11) 0.19065(11) 0.0338(3) Uani 1 1 d . . . . .
H25 H 0.166163 0.904588 0.229763 0.041 Uiso 1 1 calc R U . . .
C26 C 0.2196(2) 0.75271(11) 0.20722(10) 0.0311(3) Uani 1 1 d . . . . .
H26 H 0.307119 0.726272 0.258834 0.037 Uiso 1 1 calc R U . . .
N4 N 0.17880(16) 0.68525(8) 0.15124(8) 0.0246(2) Uani 1 1 d . . . . .
N5 N 0.03090(17) 0.64498(9) 0.02499(8) 0.0277(2) Uani 1 1 d . . . . .
H4A H 0.236(3) 0.6103(15) 0.1679(13) 0.043(5) Uiso 1 1 d . . . . .
H5A H 0.075(3) 0.5764(15) 0.0492(13) 0.039(4) Uiso 1 1 d . . . . .
H5B H -0.055(3) 0.6620(14) -0.0188(13) 0.036(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.3761(18) . ?
C1 C2 1.3817(19) . ?
C1 N1 1.4743(17) . ?
C2 C3 1.3809(19) . ?
C2 H2 0.95 . ?
C3 C4 1.3783(18) . ?
C3 N3 1.4724(17) . ?
C4 C5 1.3785(18) . ?
C4 H4 0.95 . ?
C5 C6 1.3839(18) . ?
C5 N2 1.4707(16) . ?
C6 H6 0.95 . ?
N1 O1 1.2169(18) . ?
N1 O2 1.2223(18) . ?
N2 O5 1.2187(15) . ?
N2 O6 1.2195(15) . ?
N3 O4 1.2212(17) . ?
N3 O3 1.2214(16) . ?
C7 C8 1.405(2) . ?
C7 C20 1.408(2) . ?
C7 C21 1.5147(16) . ?
C8 C9 1.427(2) . ?
C8 C13 1.443(2) . ?
C9 C10 1.365(2) . ?
C9 H9 0.95 . ?
C10 C11 1.421(4) . ?
C10 H10 0.95 . ?
C11 C12 1.336(4) . ?
C11 H11 0.95 . ?
C12 C13 1.426(3) . ?
C12 H12 0.95 . ?
C13 C14 1.391(3) . ?
C14 C15 1.380(3) . ?
C14 H13 0.95 . ?
C15 C20 1.438(2) . ?
C15 C16 1.442(3) . ?
C16 C17 1.342(4) . ?
C16 H14 0.95 . ?
C17 C18 1.403(4) . ?
C17 H15 0.95 . ?
C18 C19 1.362(2) . ?
C18 H16 0.95 . ?
C19 C20 1.426(2) . ?
C19 H17 0.95 . ?
C21 O8 1.2459(15) . ?
C21 O7 1.2610(15) . ?
C22 N5 1.3309(16) . ?
C22 N4 1.3475(16) . ?
C22 C23 1.4123(17) . ?
C23 C24 1.3656(19) . ?
C23 H23 0.95 . ?
C24 C25 1.404(2) . ?
C24 H24 0.95 . ?
C25 C26 1.3553(19) . ?
C25 H25 0.95 . ?
C26 N4 1.3560(16) . ?
C26 H26 0.95 . ?
N4 H4A 0.969(18) . ?
N5 H5A 0.886(19) . ?
N5 H5B 0.860(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
C6 C1 C2 123.40(12) . . ?
C6 C1 N1 117.83(12) . . ?
C2 C1 N1 118.76(12) . . ?
C3 C2 C1 116.64(12) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C4 C3 C2 123.35(12) . . ?
C4 C3 N3 117.61(12) . . ?
C2 C3 N3 119.04(12) . . ?
C3 C4 C5 116.59(12) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C4 C5 C6 123.47(12) . . ?
C4 C5 N2 118.16(11) . . ?
C6 C5 N2 118.36(11) . . ?
C1 C6 C5 116.50(12) . . ?
C1 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
O1 N1 O2 125.10(13) . . ?
O1 N1 C1 117.70(12) . . ?
O2 N1 C1 117.20(13) . . ?
O5 N2 O6 124.25(12) . . ?
O5 N2 C5 117.85(11) . . ?
O6 N2 C5 117.89(11) . . ?
O4 N3 O3 124.60(13) . . ?
O4 N3 C3 117.88(11) . . ?
O3 N3 C3 117.53(13) . . ?
C8 C7 C20 121.37(13) . . ?
C8 C7 C21 119.83(12) . . ?
C20 C7 C21 118.74(12) . . ?
C7 C8 C9 123.42(13) . . ?
C7 C8 C13 118.43(16) . . ?
C9 C8 C13 118.14(15) . . ?
C10 C9 C8 120.95(19) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 122.2(2) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 122.4(2) . . ?
C14 C13 C8 119.56(17) . . ?
C12 C13 C8 118.0(2) . . ?
C15 C14 C13 122.06(15) . . ?
C15 C14 H13 119 . . ?
C13 C14 H13 119 . . ?
C14 C15 C20 119.51(17) . . ?
C14 C15 C16 122.72(19) . . ?
C20 C15 C16 117.8(2) . . ?
C17 C16 C15 121.8(2) . . ?
C17 C16 H14 119.1 . . ?
C15 C16 H14 119.1 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H15 119.9 . . ?
C18 C17 H15 119.9 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H16 119.5 . . ?
C17 C18 H16 119.5 . . ?
C18 C19 C20 121.14(19) . . ?
C18 C19 H17 119.4 . . ?
C20 C19 H17 119.4 . . ?
C7 C20 C19 122.98(13) . . ?
C7 C20 C15 118.94(16) . . ?
C19 C20 C15 118.05(15) . . ?
O8 C21 O7 125.58(11) . . ?
O8 C21 C7 117.39(11) . . ?
O7 C21 C7 117.01(11) . . ?
N5 C22 N4 117.58(11) . . ?
N5 C22 C23 124.49(12) . . ?
N4 C22 C23 117.91(11) . . ?
C24 C23 C22 119.44(12) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.95(12) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 118.01(12) . . ?
C26 C25 H25 121 . . ?
C24 C25 H25 121 . . ?
C25 C26 N4 121.01(13) . . ?
C25 C26 H26 119.5 . . ?
N4 C26 H26 119.5 . . ?
C22 N4 C26 122.68(11) . . ?
C22 N4 H4A 119.2(10) . . ?
C26 N4 H4A 118.0(10) . . ?
C22 N5 H5A 117.8(11) . . ?
C22 N5 H5B 118.8(11) . . ?
H5A N5 H5B 120.5(16) . . ?

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
C6 C1 C2 C3 -0.64(19) . . . . ?
N1 C1 C2 C3 178.83(11) . . . . ?
C1 C2 C3 C4 1.71(19) . . . . ?
C1 C2 C3 N3 -178.42(11) . . . . ?
C2 C3 C4 C5 -0.77(19) . . . . ?
N3 C3 C4 C5 179.35(11) . . . . ?
C3 C4 C5 C6 -1.34(18) . . . . ?
C3 C4 C5 N2 178.03(11) . . . . ?
C2 C1 C6 C5 -1.26(19) . . . . ?
N1 C1 C6 C5 179.27(11) . . . . ?
C4 C5 C6 C1 2.30(18) . . . . ?
N2 C5 C6 C1 -177.06(11) . . . . ?
C6 C1 N1 O1 18.51(18) . . . . ?
C2 C1 N1 O1 -160.99(13) . . . . ?
C6 C1 N1 O2 -161.59(13) . . . . ?
C2 C1 N1 O2 18.91(18) . . . . ?
C4 C5 N2 O5 4.08(18) . . . . ?
C6 C5 N2 O5 -176.52(12) . . . . ?
C4 C5 N2 O6 -175.33(12) . . . . ?
C6 C5 N2 O6 4.07(18) . . . . ?
C4 C3 N3 O4 -10.60(18) . . . . ?
C2 C3 N3 O4 169.52(12) . . . . ?
C4 C3 N3 O3 168.98(13) . . . . ?
C2 C3 N3 O3 -10.90(18) . . . . ?
C20 C7 C8 C9 177.02(12) . . . . ?
C21 C7 C8 C9 -5.89(19) . . . . ?
C20 C7 C8 C13 -4.02(19) . . . . ?
C21 C7 C8 C13 173.08(11) . . . . ?
C7 C8 C9 C10 178.48(14) . . . . ?
C13 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 178.69(19) . . . . ?
C11 C12 C13 C8 -1.4(3) . . . . ?
C7 C8 C13 C14 2.7(2) . . . . ?
C9 C8 C13 C14 -178.32(14) . . . . ?
C7 C8 C13 C12 -177.26(14) . . . . ?
C9 C8 C13 C12 1.8(2) . . . . ?
C12 C13 C14 C15 -179.34(16) . . . . ?
C8 C13 C14 C15 0.7(2) . . . . ?
C13 C14 C15 C20 -2.8(2) . . . . ?
C13 C14 C15 C16 177.62(15) . . . . ?
C14 C15 C16 C17 179.85(18) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C8 C7 C20 C19 -175.70(12) . . . . ?
C21 C7 C20 C19 7.18(19) . . . . ?
C8 C7 C20 C15 2.01(19) . . . . ?
C21 C7 C20 C15 -175.11(11) . . . . ?
C18 C19 C20 C7 178.80(14) . . . . ?
C18 C19 C20 C15 1.1(2) . . . . ?
C14 C15 C20 C7 1.4(2) . . . . ?
C16 C15 C20 C7 -178.98(13) . . . . ?
C14 C15 C20 C19 179.26(14) . . . . ?
C16 C15 C20 C19 -1.2(2) . . . . ?
C8 C7 C21 O8 -121.12(13) . . . . ?
C20 C7 C21 O8 56.05(16) . . . . ?
C8 C7 C21 O7 57.38(16) . . . . ?
C20 C7 C21 O7 -125.45(13) . . . . ?
N5 C22 C23 C24 -178.56(12) . . . . ?
N4 C22 C23 C24 0.00(18) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C24 C25 C26 N4 0.2(2) . . . . ?
N5 C22 N4 C26 178.35(12) . . . . ?
C23 C22 N4 C26 -0.31(18) . . . . ?
C25 C26 N4 C22 0.2(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
C2 H2 O3 0.95 2.57 3.4298(17) 151.1 2_666 yes
C6 H6 N5 0.95 2.6 3.5308(17) 166.2 2_665 yes
C23 H23 O6 0.95 2.59 3.0739(17) 112.1 2_665 yes
C26 H26 O3 0.95 2.65 3.4838(18) 147.2 2_666 yes
C26 H26 O4 0.95 2.52 3.2300(17) 131.3 2_666 yes
N4 H4A O7 0.969(18) 1.648(19) 2.5993(14) 166.2(16) . yes
N5 H5A O8 0.886(19) 1.986(19) 2.8570(15) 167.3(16) . yes
N5 H5B O8 0.860(18) 2.271(17) 2.9147(14) 131.7(14) 2_565 yes

####################################################################### 
# 
# 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_Form_II
_database_code_depnum_ccdc_archive 'CCDC 2001330'
loop_
_audit_author_name
_audit_author_address
'Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2020-05-06 deposited with the CCDC.	2020-07-30 downloaded from the CCDC.
;

_audit_creation_date             2020-03-30T07:36:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H9 O2, C6 H3 N3 O6, C5 H7 N2'
_chemical_formula_sum            'C26 H19 N5 O8'
_chemical_formula_weight         529.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8923(11)
_cell_length_b                   18.908(3)
_cell_length_c                   15.969(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.838(5)
_cell_angle_gamma                90
_cell_volume                     2370.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9725
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      28.32
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.683
_exptl_crystal_size_mid          0.436
_exptl_crystal_size_min          0.26
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 0 0.108
-1 1 0 0.224
1 0 1 0.141
-1 0 -1 0.218
0 1 0 0.13
0 -1 0 0.118
0 1 1 0.166
0 -1 -1 0.166
0 0 1 0.288
0 0 -1 0.209
-1 0 1 0.276
1 0 -1 0.152

_exptl_special_details           
;
 Absorption corrections were made using the program SADABS
        (Sheldrick, 1996)
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.7179
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_number            104798
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.976
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             5709
_reflns_number_gt                5160
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2016)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
        Ortep for Windows (Farrugia, 2012)'
;
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.9342P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5709
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.00092(13) 0.20863(6) 0.45031(7) 0.0236(2) Uani 1 1 d . . . . .
C2 C -0.06260(13) 0.24040(6) 0.51893(7) 0.0240(2) Uani 1 1 d . . . . .
H2 H -0.083538 0.214136 0.56754 0.029 Uiso 1 1 calc R U . . .
C3 C -0.09235(13) 0.31244(6) 0.51325(7) 0.0239(2) Uani 1 1 d . . . . .
C4 C -0.06063(13) 0.35261(6) 0.44446(7) 0.0250(2) Uani 1 1 d . . . . .
H4 H -0.081816 0.402067 0.44241 0.03 Uiso 1 1 calc R U . . .
C5 C 0.00332(14) 0.31753(6) 0.37880(7) 0.0256(2) Uani 1 1 d . . . . .
C6 C 0.03433(14) 0.24559(6) 0.37971(7) 0.0265(2) Uani 1 1 d . . . . .
H6 H 0.0781 0.222565 0.333615 0.032 Uiso 1 1 calc R U . . .
N1 N 0.02378(12) 0.13144(5) 0.45112(7) 0.0293(2) Uani 1 1 d . . . . .
N2 N -0.16416(13) 0.34831(6) 0.58351(7) 0.0316(2) Uani 1 1 d . . . . .
N3 N 0.03332(15) 0.35791(6) 0.30293(7) 0.0356(2) Uani 1 1 d . . . . .
O1 O 0.08191(13) 0.10453(5) 0.39003(7) 0.0402(2) Uani 1 1 d . . . . .
O2 O -0.01650(12) 0.09846(5) 0.51155(7) 0.0411(2) Uani 1 1 d . . . . .
O3 O -0.17116(15) 0.31506(6) 0.64857(6) 0.0467(3) Uani 1 1 d . . . . .
O4 O -0.21168(14) 0.40943(6) 0.57309(7) 0.0462(3) Uani 1 1 d . . . . .
O5 O 0.00441(15) 0.42129(5) 0.30277(7) 0.0482(3) Uani 1 1 d . . . . .
O6 O 0.08289(19) 0.32556(6) 0.24395(7) 0.0582(3) Uani 1 1 d . . . . .
C7 C 0.44232(12) 0.27423(5) 0.49458(6) 0.01864(19) Uani 1 1 d . . . . .
C8 C 0.36591(13) 0.32237(5) 0.54635(6) 0.0198(2) Uani 1 1 d . . . . .
C9 C 0.30786(14) 0.30255(6) 0.62516(7) 0.0257(2) Uani 1 1 d . . . . .
H9 H 0.321787 0.255182 0.644472 0.031 Uiso 1 1 calc R U . . .
C10 C 0.23292(16) 0.35093(7) 0.67267(8) 0.0325(3) Uani 1 1 d . . . . .
H10 H 0.195046 0.336621 0.724667 0.039 Uiso 1 1 calc R U . . .
C11 C 0.21015(17) 0.42218(7) 0.64630(8) 0.0341(3) Uani 1 1 d . . . . .
H11 H 0.156616 0.454965 0.680207 0.041 Uiso 1 1 calc R U . . .
C12 C 0.26502(15) 0.44345(6) 0.57250(8) 0.0297(2) Uani 1 1 d . . . . .
H12 H 0.250385 0.491375 0.555393 0.036 Uiso 1 1 calc R U . . .
C13 C 0.34457(13) 0.39482(5) 0.52003(7) 0.0219(2) Uani 1 1 d . . . . .
C14 C 0.39979(14) 0.41653(5) 0.44397(7) 0.0236(2) Uani 1 1 d . . . . .
H14 H 0.385853 0.464544 0.427122 0.028 Uiso 1 1 calc R U . . .
C15 C 0.47506(13) 0.36913(5) 0.39217(6) 0.0204(2) Uani 1 1 d . . . . .
C16 C 0.53183(15) 0.39094(6) 0.31399(7) 0.0262(2) Uani 1 1 d . . . . .
H16 H 0.521509 0.439185 0.297644 0.031 Uiso 1 1 calc R U . . .
C17 C 0.60018(16) 0.34396(7) 0.26276(7) 0.0296(2) Uani 1 1 d . . . . .
H17 H 0.636518 0.359331 0.21084 0.036 Uiso 1 1 calc R U . . .
C18 C 0.61745(15) 0.27174(6) 0.28673(7) 0.0287(2) Uani 1 1 d . . . . .
H18 H 0.663668 0.238966 0.250109 0.034 Uiso 1 1 calc R U . . .
C19 C 0.56872(14) 0.24890(6) 0.36139(7) 0.0241(2) Uani 1 1 d . . . . .
H19 H 0.583285 0.200534 0.376533 0.029 Uiso 1 1 calc R U . . .
C20 C 0.49600(12) 0.29636(5) 0.41744(6) 0.01851(19) Uani 1 1 d . . . . .
C21 C 0.46734(13) 0.19768(5) 0.52177(7) 0.0207(2) Uani 1 1 d . . . . .
O7 O 0.33455(10) 0.16233(4) 0.52977(6) 0.0312(2) Uani 1 1 d . . . . .
O8 O 0.61486(10) 0.17464(4) 0.53472(7) 0.0356(2) Uani 1 1 d . . . . .
C22 C 0.52570(14) 0.00618(5) 0.61869(6) 0.0209(2) Uani 1 1 d . . . . .
C23 C 0.53422(15) -0.05620(6) 0.66726(7) 0.0272(2) Uani 1 1 d . . . . .
H23 H 0.631243 -0.086073 0.668606 0.033 Uiso 1 1 calc R U . . .
C24 C 0.40196(17) -0.07344(6) 0.71240(8) 0.0302(2) Uani 1 1 d . . . . .
H24 H 0.409274 -0.114649 0.746622 0.036 Uiso 1 1 calc R U . . .
C25 C 0.25589(16) -0.03112(6) 0.70882(7) 0.0290(2) Uani 1 1 d . . . . .
H25 H 0.163868 -0.04292 0.740206 0.035 Uiso 1 1 calc R U . . .
C26 C 0.24960(14) 0.02757(6) 0.65894(7) 0.0253(2) Uani 1 1 d . . . . .
H26 H 0.150833 0.056594 0.654637 0.03 Uiso 1 1 calc R U . . .
N4 N 0.38231(11) 0.04507(5) 0.61541(5) 0.02056(18) Uani 1 1 d . . . . .
N5 N 0.65323(13) 0.02921(5) 0.57645(6) 0.0269(2) Uani 1 1 d . . . . .
H4A H 0.374(2) 0.0873(9) 0.5817(10) 0.039(4) Uiso 1 1 d . . . . .
H5A H 0.650(2) 0.0735(10) 0.5568(10) 0.044(4) Uiso 1 1 d . . . . .
H5B H 0.746(2) 0.0045(9) 0.5798(10) 0.040(4) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.3786(16) . ?
C1 C2 1.3810(16) . ?
C1 N1 1.4725(14) . ?
C2 C3 1.3837(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3792(16) . ?
C3 N2 1.4729(14) . ?
C4 C5 1.3791(16) . ?
C4 H4 0.95 . ?
C5 C6 1.3819(16) . ?
C5 N3 1.4716(15) . ?
C6 H6 0.95 . ?
N1 O2 1.2180(14) . ?
N1 O1 1.2297(14) . ?
N2 O3 1.2206(15) . ?
N2 O4 1.2211(15) . ?
N3 O5 1.2199(15) . ?
N3 O6 1.2204(15) . ?
C7 C8 1.4061(14) . ?
C7 C20 1.4066(14) . ?
C7 C21 1.5181(14) . ?
C8 C9 1.4324(14) . ?
C8 C13 1.4378(14) . ?
C9 C10 1.3615(17) . ?
C9 H9 0.95 . ?
C10 C11 1.4174(19) . ?
C10 H10 0.95 . ?
C11 C12 1.3573(18) . ?
C11 H11 0.95 . ?
C12 C13 1.4313(15) . ?
C12 H12 0.95 . ?
C13 C14 1.3935(15) . ?
C14 C15 1.3930(15) . ?
C14 H14 0.95 . ?
C15 C16 1.4295(15) . ?
C15 C20 1.4385(14) . ?
C16 C17 1.3563(17) . ?
C16 H16 0.95 . ?
C17 C18 1.4210(17) . ?
C17 H17 0.95 . ?
C18 C19 1.3598(16) . ?
C18 H18 0.95 . ?
C19 C20 1.4285(15) . ?
C19 H19 0.95 . ?
C21 O8 1.2406(13) . ?
C21 O7 1.2605(13) . ?
C22 N5 1.3401(14) . ?
C22 N4 1.3462(14) . ?
C22 C23 1.4096(15) . ?
C23 C24 1.3670(17) . ?
C23 H23 0.95 . ?
C24 C25 1.3998(18) . ?
C24 H24 0.95 . ?
C25 C26 1.3641(16) . ?
C25 H25 0.95 . ?
C26 N4 1.3557(14) . ?
C26 H26 0.95 . ?
N4 H4A 0.960(17) . ?
N5 H5A 0.894(18) . ?
N5 H5B 0.864(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
C6 C1 C2 123.04(10) . . ?
C6 C1 N1 118.17(10) . . ?
C2 C1 N1 118.76(10) . . ?
C1 C2 C3 116.57(10) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 123.44(10) . . ?
C4 C3 N2 117.92(10) . . ?
C2 C3 N2 118.64(10) . . ?
C5 C4 C3 116.80(10) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 H4 121.6 . . ?
C4 C5 C6 122.92(10) . . ?
C4 C5 N3 118.59(10) . . ?
C6 C5 N3 118.44(10) . . ?
C1 C6 C5 117.21(10) . . ?
C1 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
O2 N1 O1 124.43(11) . . ?
O2 N1 C1 118.00(10) . . ?
O1 N1 C1 117.57(10) . . ?
O3 N2 O4 124.31(11) . . ?
O3 N2 C3 117.74(11) . . ?
O4 N2 C3 117.94(10) . . ?
O5 N3 O6 124.43(11) . . ?
O5 N3 C5 117.76(11) . . ?
O6 N3 C5 117.80(11) . . ?
C8 C7 C20 120.50(9) . . ?
C8 C7 C21 120.01(9) . . ?
C20 C7 C21 119.48(9) . . ?
C7 C8 C9 122.81(10) . . ?
C7 C8 C13 119.31(9) . . ?
C9 C8 C13 117.88(10) . . ?
C10 C9 C8 120.65(11) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 121.48(11) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 119.85(11) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.03(11) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.04(10) . . ?
C14 C13 C8 119.85(9) . . ?
C12 C13 C8 119.10(10) . . ?
C15 C14 C13 121.20(9) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.56(10) . . ?
C14 C15 C20 119.51(9) . . ?
C16 C15 C20 118.93(10) . . ?
C17 C16 C15 121.14(10) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.00(10) . . ?
C16 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C19 C18 C17 120.89(11) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.16(10) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C7 C20 C19 122.54(9) . . ?
C7 C20 C15 119.61(9) . . ?
C19 C20 C15 117.84(9) . . ?
O8 C21 O7 124.94(10) . . ?
O8 C21 C7 118.36(9) . . ?
O7 C21 C7 116.69(9) . . ?
N5 C22 N4 118.32(10) . . ?
N5 C22 C23 123.55(10) . . ?
N4 C22 C23 118.13(10) . . ?
C24 C23 C22 119.57(11) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.80(11) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 118.03(11) . . ?
C26 C25 H25 121 . . ?
C24 C25 H25 121 . . ?
N4 C26 C25 120.92(10) . . ?
N4 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C22 N4 C26 122.48(9) . . ?
C22 N4 H4A 119.2(10) . . ?
C26 N4 H4A 118.3(10) . . ?
C22 N5 H5A 118.9(11) . . ?
C22 N5 H5B 117.8(11) . . ?
H5A N5 H5B 121.6(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.51(16) . . . . ?
N1 C1 C2 C3 -176.59(9) . . . . ?
C1 C2 C3 C4 -1.24(16) . . . . ?
C1 C2 C3 N2 177.77(9) . . . . ?
C2 C3 C4 C5 0.30(16) . . . . ?
N2 C3 C4 C5 -178.72(10) . . . . ?
C3 C4 C5 C6 0.46(17) . . . . ?
C3 C4 C5 N3 177.87(10) . . . . ?
C2 C1 C6 C5 -0.83(16) . . . . ?
N1 C1 C6 C5 177.29(10) . . . . ?
C4 C5 C6 C1 -0.21(17) . . . . ?
N3 C5 C6 C1 -177.63(10) . . . . ?
C6 C1 N1 O2 -175.96(10) . . . . ?
C2 C1 N1 O2 2.24(15) . . . . ?
C6 C1 N1 O1 3.16(15) . . . . ?
C2 C1 N1 O1 -178.64(10) . . . . ?
C4 C3 N2 O3 -170.53(11) . . . . ?
C2 C3 N2 O3 10.41(16) . . . . ?
C4 C3 N2 O4 8.99(16) . . . . ?
C2 C3 N2 O4 -170.07(11) . . . . ?
C4 C5 N3 O5 2.02(17) . . . . ?
C6 C5 N3 O5 179.55(12) . . . . ?
C4 C5 N3 O6 -176.87(12) . . . . ?
C6 C5 N3 O6 0.66(18) . . . . ?
C20 C7 C8 C9 179.55(9) . . . . ?
C21 C7 C8 C9 -0.41(15) . . . . ?
C20 C7 C8 C13 -0.60(14) . . . . ?
C21 C7 C8 C13 179.44(9) . . . . ?
C7 C8 C9 C10 -179.28(10) . . . . ?
C13 C8 C9 C10 0.87(16) . . . . ?
C8 C9 C10 C11 -0.19(18) . . . . ?
C9 C10 C11 C12 -0.56(19) . . . . ?
C10 C11 C12 C13 0.59(19) . . . . ?
C11 C12 C13 C14 179.53(11) . . . . ?
C11 C12 C13 C8 0.11(17) . . . . ?
C7 C8 C13 C14 -0.12(15) . . . . ?
C9 C8 C13 C14 179.74(10) . . . . ?
C7 C8 C13 C12 179.32(10) . . . . ?
C9 C8 C13 C12 -0.82(15) . . . . ?
C12 C13 C14 C15 -179.07(10) . . . . ?
C8 C13 C14 C15 0.35(16) . . . . ?
C13 C14 C15 C16 179.91(10) . . . . ?
C13 C14 C15 C20 0.13(16) . . . . ?
C14 C15 C16 C17 -177.94(11) . . . . ?
C20 C15 C16 C17 1.83(16) . . . . ?
C15 C16 C17 C18 -0.44(18) . . . . ?
C16 C17 C18 C19 -1.05(18) . . . . ?
C17 C18 C19 C20 1.09(18) . . . . ?
C8 C7 C20 C19 -177.74(9) . . . . ?
C21 C7 C20 C19 2.22(15) . . . . ?
C8 C7 C20 C15 1.08(14) . . . . ?
C21 C7 C20 C15 -178.96(9) . . . . ?
C18 C19 C20 C7 179.17(10) . . . . ?
C18 C19 C20 C15 0.33(16) . . . . ?
C14 C15 C20 C7 -0.84(15) . . . . ?
C16 C15 C20 C7 179.37(9) . . . . ?
C14 C15 C20 C19 178.03(9) . . . . ?
C16 C15 C20 C19 -1.75(14) . . . . ?
C8 C7 C21 O8 -116.76(12) . . . . ?
C20 C7 C21 O8 63.28(14) . . . . ?
C8 C7 C21 O7 62.95(13) . . . . ?
C20 C7 C21 O7 -117.01(11) . . . . ?
N5 C22 C23 C24 176.05(11) . . . . ?
N4 C22 C23 C24 -3.19(16) . . . . ?
C22 C23 C24 C25 2.09(18) . . . . ?
C23 C24 C25 C26 0.12(18) . . . . ?
C24 C25 C26 N4 -1.24(17) . . . . ?
N5 C22 N4 C26 -177.14(10) . . . . ?
C23 C22 N4 C26 2.15(15) . . . . ?
C25 C26 N4 C22 0.07(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
C23 H23 O1 0.95 2.56 3.3786(16) 144.4 3_656 yes
N4 H4A O7 0.960(17) 1.657(17) 2.6121(12) 172.2(15) . yes
N5 H5A O8 0.894(18) 1.959(19) 2.8385(14) 167.6(15) . yes
N5 H5B O1 0.864(18) 2.490(18) 3.2899(14) 154.4(14) 3_656 yes

