# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_2
_audit_block_doi                 10.5517/ccdc.csd.cc1j2t3j
_database_code_depnum_ccdc_archive 'CCDC 1402877'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-05T11:16:41-00:00
_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                   6.8850(11)
_cell_length_b                   13.936(2)
_cell_length_c                   24.919(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.600(5)
_cell_angle_gamma                90
_cell_volume                     2333.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      28.21
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_T_max  0.9943
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.994

#----------------------------------------------------------------------------#
#                   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  0.1282
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_number            29055
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.907
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_reflns_Friedel_coverage         0
_reflns_number_total             4373
_reflns_number_gt                3366
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1386P)²+7.3608P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4373
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.108
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2734
_refine_ls_wR_factor_gt          0.253
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.04
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.197

#----------------------------------------------------------------------------#
#                   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 0.8605(7) 0.3355(3) 0.6856(2) 0.0319(10) Uani 1 1 d . . . . .
C2 C 0.8632(7) 0.3186(4) 0.7401(2) 0.0338(11) Uani 1 1 d . . . . .
H2 H 0.882542 0.368942 0.766473 0.041 Uiso 1 1 calc R U . . .
C3 C 0.8363(7) 0.2248(4) 0.75464(19) 0.0331(11) Uani 1 1 d . . . . .
C4 C 0.8103(7) 0.1504(4) 0.7180(2) 0.0345(11) Uani 1 1 d . . . . .
H4A H 0.793965 0.086273 0.729209 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8088(7) 0.1731(3) 0.6635(2) 0.0324(11) Uani 1 1 d . . . . .
C6 C 0.8339(7) 0.2652(3) 0.6462(2) 0.0317(10) Uani 1 1 d . . . . .
H6 H 0.832865 0.279325 0.608849 0.038 Uiso 1 1 calc R U . . .
N1 N 0.8865(6) 0.4350(3) 0.66880(17) 0.0340(9) Uani 1 1 d . . . . .
N2 N 0.8324(6) 0.2037(3) 0.81260(18) 0.0410(11) Uani 1 1 d . . . . .
N3 N 0.7780(6) 0.0948(3) 0.62273(19) 0.0395(10) Uani 1 1 d . . . . .
O1 O 0.9300(6) 0.4476(3) 0.62447(15) 0.0406(9) Uani 1 1 d . . . . .
O2 O 0.8633(6) 0.4994(3) 0.70006(16) 0.0477(10) Uani 1 1 d . . . . .
O3 O 0.8836(7) 0.2688(3) 0.84610(16) 0.0551(11) Uani 1 1 d . . . . .
O4 O 0.7802(7) 0.1240(3) 0.82332(18) 0.0581(12) Uani 1 1 d . . . . .
O5 O 0.7634(7) 0.0129(3) 0.63941(19) 0.0567(11) Uani 1 1 d . . . . .
O6 O 0.7686(6) 0.1156(3) 0.57494(17) 0.0487(10) Uani 1 1 d . . . . .
C11 C 0.3187(6) 0.2743(3) 0.62350(18) 0.0262(10) Uani 1 1 d . . . . .
C12 C 0.3428(6) 0.2946(3) 0.67978(18) 0.0248(9) Uani 1 1 d . . . . .
C13 C 0.3786(7) 0.3891(3) 0.70222(19) 0.0293(10) Uani 1 1 d . . . . .
H13 H 0.387075 0.441525 0.678504 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4005(7) 0.4047(4) 0.7569(2) 0.0356(11) Uani 1 1 d . . . . .
H14 H 0.423314 0.468159 0.770745 0.043 Uiso 1 1 calc R U . . .
C15 C 0.3904(8) 0.3294(4) 0.7938(2) 0.0382(12) Uani 1 1 d . . . . .
H15 H 0.408182 0.342156 0.832017 0.046 Uiso 1 1 calc R U . . .
C16 C 0.3550(7) 0.2384(4) 0.77461(19) 0.0328(11) Uani 1 1 d . . . . .
H16 H 0.346474 0.18789 0.79958 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3306(6) 0.2179(3) 0.7178(2) 0.0283(10) Uani 1 1 d . . . . .
C18 C 0.2934(7) 0.1248(3) 0.6979(2) 0.0321(11) Uani 1 1 d . . . . .
H18 H 0.284387 0.074404 0.722877 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2691(7) 0.1038(3) 0.6422(2) 0.0309(10) Uani 1 1 d . . . . .
C20 C 0.2330(8) 0.0082(4) 0.6222(2) 0.0421(13) Uani 1 1 d . . . . .
H20 H 0.225222 -0.042502 0.647113 0.05 Uiso 1 1 calc R U . . .
C21 C 0.2096(8) -0.0111(4) 0.5679(3) 0.0473(14) Uani 1 1 d . . . . .
H21 H 0.18519 -0.075064 0.555129 0.057 Uiso 1 1 calc R U . . .
C22 C 0.2212(8) 0.0628(4) 0.5304(2) 0.0491(15) Uani 1 1 d . . . . .
H22 H 0.206476 0.047898 0.492528 0.059 Uiso 1 1 calc R U . . .
C23 C 0.2531(8) 0.1554(4) 0.5474(2) 0.0382(12) Uani 1 1 d . . . . .
H23 H 0.257489 0.20437 0.5212 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2801(7) 0.1799(3) 0.6042(2) 0.0303(10) Uani 1 1 d . . . . .
C25 C 0.3350(7) 0.3556(3) 0.58400(19) 0.0308(10) Uani 1 1 d . . . . .
O11 O 0.4959(5) 0.4015(3) 0.59347(15) 0.0391(9) Uani 1 1 d . . . . .
O12 O 0.1914(5) 0.3705(3) 0.54493(14) 0.0389(9) Uani 1 1 d . . . . .
C26 C 0.3410(8) 0.6241(4) 0.5322(2) 0.0387(12) Uani 1 1 d . . . . .
C27 C 0.3312(8) 0.7250(4) 0.5247(2) 0.0425(13) Uani 1 1 d . . . . .
H27 H 0.212939 0.754201 0.504563 0.051 Uiso 1 1 calc R U . . .
C28 C 0.4924(9) 0.7791(4) 0.5464(2) 0.0429(13) Uani 1 1 d . . . . .
H28 H 0.48514 0.846749 0.54171 0.052 Uiso 1 1 calc R U . . .
C29 C 0.6679(8) 0.7383(4) 0.5755(2) 0.0399(12) Uani 1 1 d . . . . .
H29 H 0.780709 0.776893 0.590173 0.048 Uiso 1 1 calc R U . . .
C30 C 0.6737(8) 0.6413(4) 0.5824(2) 0.0390(12) Uani 1 1 d . . . . .
H30 H 0.792624 0.611524 0.601755 0.047 Uiso 1 1 calc R U . . .
N4 N 0.5114(6) 0.5868(3) 0.56182(17) 0.0369(10) Uani 1 1 d . . . . .
N5 N 0.1930(8) 0.5656(4) 0.5121(2) 0.0552(14) Uani 1 1 d . . . . .
H4 H 0.512(9) 0.515(5) 0.573(3) 0.056(18) Uiso 1 1 d . . . . .
H5A H 0.182(12) 0.499(6) 0.522(3) 0.09(2) Uiso 1 1 d . . . . .
H5B H 0.079(9) 0.591(4) 0.490(2) 0.033(14) 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 1.372(7) . ?
C1 C2 1.374(7) . ?
C1 N1 1.471(6) . ?
C2 C3 1.379(7) . ?
C2 H2 0.95 . ?
C3 C4 1.367(7) . ?
C3 N2 1.480(7) . ?
C4 C5 1.394(7) . ?
C4 H4A 0.95 . ?
C5 C6 1.376(7) . ?
C5 N3 1.474(6) . ?
C6 H6 0.95 . ?
N1 O1 1.218(5) . ?
N1 O2 1.221(5) . ?
N2 O4 1.215(6) . ?
N2 O3 1.232(6) . ?
N3 O6 1.214(6) . ?
N3 O5 1.225(6) . ?
C11 C12 1.404(6) . ?
C11 C24 1.406(6) . ?
C11 C25 1.521(6) . ?
C12 C13 1.430(6) . ?
C12 C17 1.443(6) . ?
C13 C14 1.356(7) . ?
C13 H13 0.95 . ?
C14 C15 1.406(8) . ?
C14 H14 0.95 . ?
C15 C16 1.358(7) . ?
C15 H15 0.95 . ?
C16 C17 1.418(7) . ?
C16 H16 0.95 . ?
C17 C18 1.393(7) . ?
C18 C19 1.391(7) . ?
C18 H18 0.95 . ?
C19 C20 1.426(7) . ?
C19 C24 1.436(7) . ?
C20 C21 1.352(8) . ?
C20 H20 0.95 . ?
C21 C22 1.405(9) . ?
C21 H21 0.95 . ?
C22 C23 1.361(8) . ?
C22 H22 0.95 . ?
C23 C24 1.426(7) . ?
C23 H23 0.95 . ?
C25 O12 1.244(6) . ?
C25 O11 1.256(6) . ?
C26 N5 1.315(7) . ?
C26 N4 1.346(7) . ?
C26 C27 1.418(7) . ?
C27 C28 1.353(8) . ?
C27 H27 0.95 . ?
C28 C29 1.388(8) . ?
C28 H28 0.95 . ?
C29 C30 1.362(8) . ?
C29 H29 0.95 . ?
C30 N4 1.356(7) . ?
C30 H30 0.95 . ?
N4 H4 1.04(7) . ?
N5 H5A 0.97(8) . ?
N5 H5B 0.92(6) . ?

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 123.8(5) . . ?
C6 C1 N1 118.3(4) . . ?
C2 C1 N1 117.9(4) . . ?
C1 C2 C3 116.6(5) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 123.3(5) . . ?
C4 C3 N2 118.2(5) . . ?
C2 C3 N2 118.4(5) . . ?
C3 C4 C5 116.8(5) . . ?
C3 C4 H4A 121.6 . . ?
C5 C4 H4A 121.6 . . ?
C6 C5 C4 122.8(5) . . ?
C6 C5 N3 119.0(4) . . ?
C4 C5 N3 118.2(4) . . ?
C1 C6 C5 116.7(5) . . ?
C1 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
O1 N1 O2 124.4(4) . . ?
O1 N1 C1 117.6(4) . . ?
O2 N1 C1 118.0(4) . . ?
O4 N2 O3 125.4(5) . . ?
O4 N2 C3 117.7(5) . . ?
O3 N2 C3 116.8(5) . . ?
O6 N3 O5 124.3(5) . . ?
O6 N3 C5 117.9(4) . . ?
O5 N3 C5 117.8(5) . . ?
C12 C11 C24 120.2(4) . . ?
C12 C11 C25 119.1(4) . . ?
C24 C11 C25 120.7(4) . . ?
C11 C12 C13 123.3(4) . . ?
C11 C12 C17 119.7(4) . . ?
C13 C12 C17 117.1(4) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.8(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C15 C14 119.8(5) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.9(5) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 C12 119.2(4) . . ?
C16 C17 C12 119.6(4) . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 121.3(5) . . ?
C18 C19 C24 119.4(4) . . ?
C20 C19 C24 119.3(5) . . ?
C21 C20 C19 120.6(5) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.6(5) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 121.0(5) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.9(5) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C11 C24 C23 122.5(5) . . ?
C11 C24 C19 119.9(4) . . ?
C23 C24 C19 117.6(4) . . ?
O12 C25 O11 125.4(4) . . ?
O12 C25 C11 118.2(4) . . ?
O11 C25 C11 116.4(4) . . ?
N5 C26 N4 118.7(5) . . ?
N5 C26 C27 123.6(5) . . ?
N4 C26 C27 117.7(5) . . ?
C28 C27 C26 119.2(5) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C27 C28 C29 121.7(5) . . ?
C27 C28 H28 119.2 . . ?
C29 C28 H28 119.2 . . ?
C30 C29 C28 118.1(5) . . ?
C30 C29 H29 121 . . ?
C28 C29 H29 121 . . ?
N4 C30 C29 120.6(5) . . ?
N4 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C26 N4 C30 122.6(5) . . ?
C26 N4 H4 118(4) . . ?
C30 N4 H4 119(4) . . ?
C26 N5 H5A 126(5) . . ?
C26 N5 H5B 119(3) . . ?
H5A N5 H5B 114(6) . . ?

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 -0.3(7) . . . . ?
N1 C1 C2 C3 179.3(4) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C1 C2 C3 N2 -178.3(4) . . . . ?
C2 C3 C4 C5 -0.9(7) . . . . ?
N2 C3 C4 C5 178.1(4) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C3 C4 C5 N3 -179.1(4) . . . . ?
C2 C1 C6 C5 0.0(7) . . . . ?
N1 C1 C6 C5 -179.6(4) . . . . ?
C4 C5 C6 C1 -0.2(7) . . . . ?
N3 C5 C6 C1 179.5(4) . . . . ?
C6 C1 N1 O1 -17.0(6) . . . . ?
C2 C1 N1 O1 163.4(4) . . . . ?
C6 C1 N1 O2 163.1(4) . . . . ?
C2 C1 N1 O2 -16.5(7) . . . . ?
C4 C3 N2 O4 -9.6(7) . . . . ?
C2 C3 N2 O4 169.5(5) . . . . ?
C4 C3 N2 O3 170.1(5) . . . . ?
C2 C3 N2 O3 -10.8(7) . . . . ?
C6 C5 N3 O6 -2.7(7) . . . . ?
C4 C5 N3 O6 177.0(4) . . . . ?
C6 C5 N3 O5 177.3(5) . . . . ?
C4 C5 N3 O5 -2.9(7) . . . . ?
C24 C11 C12 C13 -178.8(4) . . . . ?
C25 C11 C12 C13 1.2(6) . . . . ?
C24 C11 C12 C17 0.9(6) . . . . ?
C25 C11 C12 C17 -179.1(4) . . . . ?
C11 C12 C13 C14 179.9(4) . . . . ?
C17 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C13 C14 C15 C16 -0.9(8) . . . . ?
C14 C15 C16 C17 0.8(7) . . . . ?
C15 C16 C17 C18 -179.7(5) . . . . ?
C15 C16 C17 C12 -0.2(7) . . . . ?
C11 C12 C17 C18 -0.5(6) . . . . ?
C13 C12 C17 C18 179.2(4) . . . . ?
C11 C12 C17 C16 180.0(4) . . . . ?
C13 C12 C17 C16 -0.3(6) . . . . ?
C16 C17 C18 C19 180.0(4) . . . . ?
C12 C17 C18 C19 0.5(7) . . . . ?
C17 C18 C19 C20 179.4(4) . . . . ?
C17 C18 C19 C24 -0.8(7) . . . . ?
C18 C19 C20 C21 180.0(5) . . . . ?
C24 C19 C20 C21 0.1(7) . . . . ?
C19 C20 C21 C22 0.2(8) . . . . ?
C20 C21 C22 C23 -1.0(9) . . . . ?
C21 C22 C23 C24 1.4(8) . . . . ?
C12 C11 C24 C23 179.6(4) . . . . ?
C25 C11 C24 C23 -0.4(7) . . . . ?
C12 C11 C24 C19 -1.2(6) . . . . ?
C25 C11 C24 C19 178.8(4) . . . . ?
C22 C23 C24 C11 178.2(5) . . . . ?
C22 C23 C24 C19 -1.0(7) . . . . ?
C18 C19 C24 C11 1.2(7) . . . . ?
C20 C19 C24 C11 -179.0(4) . . . . ?
C18 C19 C24 C23 -179.6(4) . . . . ?
C20 C19 C24 C23 0.2(6) . . . . ?
C12 C11 C25 O12 -122.9(5) . . . . ?
C24 C11 C25 O12 57.1(6) . . . . ?
C12 C11 C25 O11 58.1(6) . . . . ?
C24 C11 C25 O11 -121.9(5) . . . . ?
N5 C26 C27 C28 -179.2(6) . . . . ?
N4 C26 C27 C28 1.0(8) . . . . ?
C26 C27 C28 C29 0.7(8) . . . . ?
C27 C28 C29 C30 -0.9(8) . . . . ?
C28 C29 C30 N4 -0.7(8) . . . . ?
N5 C26 N4 C30 177.5(5) . . . . ?
C27 C26 N4 C30 -2.6(8) . . . . ?
C29 C30 N4 C26 2.5(8) . . . . ?

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
N4 H4 O11 1.04(7) 1.67(7) 2.708(5) 174(6) . yes
N5 H5A O12 0.97(8) 1.88(9) 2.840(6) 174(7) . yes
N5 H5B O12 0.92(6) 1.96(6) 2.860(6) 168(5) 3_566 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_5
_audit_block_doi                 10.5517/ccdc.csd.cc1j2t7n
_database_code_depnum_ccdc_archive 'CCDC 1402881'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T07:44:15-00:00
_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 H10 O2, C6 H3 N3 O6, C5 H5 Br N2'
_chemical_formula_sum            'C26 H18 Br N5 O8'
_chemical_formula_weight         608.36

#----------------------------------------------------------------------------#
#                   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                   8.9809(6)
_cell_length_b                   7.3118(5)
_cell_length_c                   38.083(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.0950(10)
_cell_angle_gamma                90
_cell_volume                     2494.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.17
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.62
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    1.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.5939
_exptl_absorpt_correction_T_max  0.8475
_shelx_estimated_absorpt_T_min   0.594
_shelx_estimated_absorpt_T_max   0.848

#----------------------------------------------------------------------------#
#                   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  0.0288
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_number            23111
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             4616
_reflns_number_gt                3952
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0385P)²+1.7498P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4616
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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 -0.0360(3) 0.3305(3) 0.37615(6) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.1159(3) 0.3034(3) 0.37665(6) 0.0299(5) Uani 1 1 d . . . . .
H2 H 0.179619 0.328817 0.39707 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1716(3) 0.2382(3) 0.34633(6) 0.0279(5) Uani 1 1 d . . . . .
C4 C 0.0822(3) 0.2022(3) 0.31627(6) 0.0283(5) Uani 1 1 d . . . . .
H4 H 0.122581 0.156214 0.295634 0.034 Uiso 1 1 calc R U . . .
C5 C -0.0687(3) 0.2359(3) 0.31741(6) 0.0291(5) Uani 1 1 d . . . . .
C6 C -0.1322(3) 0.2987(3) 0.34688(6) 0.0302(5) Uani 1 1 d . . . . .
H6 H -0.236539 0.319175 0.347099 0.036 Uiso 1 1 calc R U . . .
N1 N -0.1011(3) 0.3982(3) 0.40833(6) 0.0432(6) Uani 1 1 d . . . . .
N2 N 0.3337(2) 0.2067(3) 0.34593(6) 0.0371(5) Uani 1 1 d . . . . .
N3 N -0.1654(3) 0.2049(3) 0.28510(6) 0.0438(6) Uani 1 1 d . . . . .
O1 O -0.2347(3) 0.4289(3) 0.40698(6) 0.0655(6) Uani 1 1 d . . . . .
O2 O -0.0174(3) 0.4189(3) 0.43425(5) 0.0644(6) Uani 1 1 d . . . . .
O3 O 0.4144(2) 0.2751(3) 0.36961(6) 0.0498(5) Uani 1 1 d . . . . .
O4 O 0.3764(2) 0.1154(3) 0.32167(6) 0.0500(5) Uani 1 1 d . . . . .
O5 O -0.1113(3) 0.1432(4) 0.25982(5) 0.0695(7) Uani 1 1 d . . . . .
O6 O -0.2975(2) 0.2418(5) 0.28611(6) 0.0832(8) Uani 1 1 d . . . . .
C11 C 0.1209(2) 0.7721(3) 0.36508(6) 0.0213(4) Uani 1 1 d . . . . .
C12 C 0.1643(2) 0.7047(3) 0.33296(6) 0.0233(5) Uani 1 1 d . . . . .
C13 C 0.3139(3) 0.6495(3) 0.32786(6) 0.0288(5) Uani 1 1 d . . . . .
H13 H 0.389652 0.666179 0.346305 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3493(3) 0.5737(3) 0.29698(7) 0.0361(6) Uani 1 1 d . . . . .
H14 H 0.448965 0.53582 0.294189 0.043 Uiso 1 1 calc R U . . .
C15 C 0.2388(3) 0.5506(3) 0.26895(7) 0.0394(6) Uani 1 1 d . . . . .
H15 H 0.264867 0.495705 0.247618 0.047 Uiso 1 1 calc R U . . .
C16 C 0.0967(3) 0.6055(3) 0.27212(6) 0.0368(6) Uani 1 1 d . . . . .
H16 H 0.024703 0.59191 0.252773 0.044 Uiso 1 1 calc R U . . .
C17 C 0.0536(3) 0.6837(3) 0.30412(6) 0.0280(5) Uani 1 1 d . . . . .
C18 C -0.0936(3) 0.7332(3) 0.30870(6) 0.0322(5) Uani 1 1 d . . . . .
H18 H -0.166104 0.721961 0.289406 0.039 Uiso 1 1 calc R U . . .
C19 C -0.1375(2) 0.7988(3) 0.34066(6) 0.0284(5) Uani 1 1 d . . . . .
C110 C -0.2890(3) 0.8485(3) 0.34592(8) 0.0391(6) Uani 1 1 d . . . . .
H110 H -0.36242 0.84056 0.326747 0.047 Uiso 1 1 calc R U . . .
C111 C -0.3291(3) 0.9062(4) 0.37756(8) 0.0421(7) Uani 1 1 d . . . . .
H111 H -0.430047 0.938 0.380467 0.051 Uiso 1 1 calc R U . . .
C112 C -0.2216(3) 0.9196(3) 0.40635(7) 0.0376(6) Uani 1 1 d . . . . .
H112 H -0.251713 0.957726 0.428614 0.045 Uiso 1 1 calc R U . . .
C113 C -0.0762(3) 0.8789(3) 0.40279(6) 0.0291(5) Uani 1 1 d . . . . .
H113 H -0.005469 0.891406 0.42242 0.035 Uiso 1 1 calc R U . . .
C114 C -0.0282(2) 0.8175(3) 0.36977(6) 0.0239(5) Uani 1 1 d . . . . .
C115 C 0.2347(2) 0.7981(3) 0.39560(6) 0.0226(5) Uani 1 1 d . . . . .
O11 O 0.2957(2) 0.9425(2) 0.40173(5) 0.0406(4) Uani 1 1 d . . . . .
O12 O 0.2585(2) 0.6515(2) 0.41456(5) 0.0389(4) Uani 1 1 d . . . . .
H12 H 0.310(4) 0.677(4) 0.4332(9) 0.059(10) Uiso 1 1 d . . . . .
C21 C 0.6317(3) 0.7710(3) 0.52839(6) 0.0304(5) Uani 1 1 d . . . . .
H21 H 0.69994 0.792262 0.548195 0.037 Uiso 1 1 calc R U . . .
C22 C 0.6829(2) 0.6996(3) 0.49757(6) 0.0271(5) Uani 1 1 d . . . . .
C23 C 0.5769(3) 0.6712(3) 0.46968(6) 0.0271(5) Uani 1 1 d . . . . .
H23 H 0.608564 0.620779 0.448466 0.032 Uiso 1 1 calc R U . . .
C24 C 0.4832(3) 0.8109(3) 0.53035(6) 0.0297(5) Uani 1 1 d . . . . .
H24 H 0.446977 0.858647 0.551325 0.036 Uiso 1 1 calc R U . . .
C25 C 0.3882(2) 0.7796(3) 0.50094(6) 0.0260(5) Uani 1 1 d . . . . .
N21 N 0.4325(2) 0.7115(2) 0.47135(5) 0.0257(4) Uani 1 1 d . . . . .
N22 N 0.8312(2) 0.6635(3) 0.49403(8) 0.0420(6) Uani 1 1 d . . . . .
Br21 Br 0.18092(3) 0.83344(4) 0.50083(2) 0.04058(10) Uani 1 1 d . . . . .
H22A H 0.882(4) 0.650(4) 0.5136(9) 0.054(10) Uiso 1 1 d . . . . .
H22B H 0.853(3) 0.593(4) 0.4775(8) 0.049(9) 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 C2 1.378(3) . ?
C1 C6 1.380(3) . ?
C1 N1 1.480(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.95 . ?
C3 C4 1.376(3) . ?
C3 N2 1.476(3) . ?
C4 C5 1.381(3) . ?
C4 H4 0.95 . ?
C5 C6 1.374(3) . ?
C5 N3 1.472(3) . ?
C6 H6 0.95 . ?
N1 O2 1.207(3) . ?
N1 O1 1.218(3) . ?
N2 O3 1.222(3) . ?
N2 O4 1.224(3) . ?
N3 O5 1.198(3) . ?
N3 O6 1.220(3) . ?
C11 C12 1.399(3) . ?
C11 C114 1.403(3) . ?
C11 C115 1.504(3) . ?
C12 C13 1.430(3) . ?
C12 C17 1.436(3) . ?
C13 C14 1.358(3) . ?
C13 H13 0.95 . ?
C14 C15 1.415(4) . ?
C14 H14 0.95 . ?
C15 C16 1.352(4) . ?
C15 H15 0.95 . ?
C16 C17 1.425(3) . ?
C16 H16 0.95 . ?
C17 C18 1.393(3) . ?
C18 C19 1.391(4) . ?
C18 H18 0.95 . ?
C19 C114 1.434(3) . ?
C19 C110 1.436(3) . ?
C110 C111 1.350(4) . ?
C110 H110 0.95 . ?
C111 C112 1.411(4) . ?
C111 H111 0.95 . ?
C112 C113 1.356(3) . ?
C112 H112 0.95 . ?
C113 C114 1.431(3) . ?
C113 H113 0.95 . ?
C115 O11 1.205(3) . ?
C115 O12 1.301(3) . ?
O12 H12 0.84(4) . ?
C21 C24 1.373(3) . ?
C21 C22 1.393(3) . ?
C21 H21 0.95 . ?
C22 N22 1.373(3) . ?
C22 C23 1.391(3) . ?
C23 N21 1.335(3) . ?
C23 H23 0.95 . ?
C24 C25 1.378(3) . ?
C24 H24 0.95 . ?
C25 N21 1.319(3) . ?
C25 Br21 1.902(2) . ?
N22 H22A 0.85(3) . ?
N22 H22B 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 123.3(2) . . ?
C2 C1 N1 119.0(2) . . ?
C6 C1 N1 117.6(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C4 C3 C2 122.7(2) . . ?
C4 C3 N2 118.6(2) . . ?
C2 C3 N2 118.7(2) . . ?
C3 C4 C5 117.1(2) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C6 C5 C4 123.4(2) . . ?
C6 C5 N3 118.7(2) . . ?
C4 C5 N3 117.9(2) . . ?
C5 C6 C1 116.4(2) . . ?
C5 C6 H6 121.8 . . ?
C1 C6 H6 121.8 . . ?
O2 N1 O1 124.5(2) . . ?
O2 N1 C1 117.4(2) . . ?
O1 N1 C1 118.2(2) . . ?
O3 N2 O4 125.4(2) . . ?
O3 N2 C3 117.5(2) . . ?
O4 N2 C3 117.1(2) . . ?
O5 N3 O6 124.1(2) . . ?
O5 N3 C5 118.7(2) . . ?
O6 N3 C5 117.2(2) . . ?
C12 C11 C114 121.5(2) . . ?
C12 C11 C115 120.25(18) . . ?
C114 C11 C115 118.26(19) . . ?
C11 C12 C13 122.8(2) . . ?
C11 C12 C17 119.0(2) . . ?
C13 C12 C17 118.2(2) . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 C12 119.2(2) . . ?
C16 C17 C12 118.8(2) . . ?
C19 C18 C17 122.0(2) . . ?
C19 C18 H18 119 . . ?
C17 C18 H18 119 . . ?
C18 C19 C114 119.2(2) . . ?
C18 C19 C110 122.7(2) . . ?
C114 C19 C110 118.1(2) . . ?
C111 C110 C19 121.3(2) . . ?
C111 C110 H110 119.4 . . ?
C19 C110 H110 119.4 . . ?
C110 C111 C112 120.2(2) . . ?
C110 C111 H111 119.9 . . ?
C112 C111 H111 119.9 . . ?
C113 C112 C111 121.2(2) . . ?
C113 C112 H112 119.4 . . ?
C111 C112 H112 119.4 . . ?
C112 C113 C114 120.6(2) . . ?
C112 C113 H113 119.7 . . ?
C114 C113 H113 119.7 . . ?
C11 C114 C113 122.4(2) . . ?
C11 C114 C19 119.1(2) . . ?
C113 C114 C19 118.5(2) . . ?
O11 C115 O12 124.0(2) . . ?
O11 C115 C11 122.37(19) . . ?
O12 C115 C11 113.58(18) . . ?
C115 O12 H12 110(2) . . ?
C24 C21 C22 120.4(2) . . ?
C24 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
N22 C22 C23 120.8(2) . . ?
N22 C22 C21 122.4(2) . . ?
C23 C22 C21 116.8(2) . . ?
N21 C23 C22 123.0(2) . . ?
N21 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
C21 C24 C25 117.9(2) . . ?
C21 C24 H24 121 . . ?
C25 C24 H24 121 . . ?
N21 C25 C24 123.4(2) . . ?
N21 C25 Br21 115.55(16) . . ?
C24 C25 Br21 121.08(18) . . ?
C25 N21 C23 118.51(19) . . ?
C22 N22 H22A 113(2) . . ?
C22 N22 H22B 118(2) . . ?
H22A N22 H22B 116(3) . . ?

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 -1.3(3) . . . . ?
N1 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 N2 -179.7(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
N2 C3 C4 C5 -179.0(2) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C3 C4 C5 N3 177.7(2) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
N3 C5 C6 C1 -178.2(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
N1 C1 C6 C5 180.0(2) . . . . ?
C2 C1 N1 O2 -3.3(3) . . . . ?
C6 C1 N1 O2 177.2(2) . . . . ?
C2 C1 N1 O1 176.9(2) . . . . ?
C6 C1 N1 O1 -2.7(3) . . . . ?
C4 C3 N2 O3 164.6(2) . . . . ?
C2 C3 N2 O3 -15.0(3) . . . . ?
C4 C3 N2 O4 -14.8(3) . . . . ?
C2 C3 N2 O4 165.6(2) . . . . ?
C6 C5 N3 O5 -177.0(3) . . . . ?
C4 C5 N3 O5 3.9(4) . . . . ?
C6 C5 N3 O6 1.8(4) . . . . ?
C4 C5 N3 O6 -177.3(3) . . . . ?
C114 C11 C12 C13 -177.1(2) . . . . ?
C115 C11 C12 C13 3.1(3) . . . . ?
C114 C11 C12 C17 0.7(3) . . . . ?
C115 C11 C12 C17 -179.12(19) . . . . ?
C11 C12 C13 C14 175.6(2) . . . . ?
C17 C12 C13 C14 -2.2(3) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -1.7(4) . . . . ?
C15 C16 C17 C18 -176.8(2) . . . . ?
C15 C16 C17 C12 0.6(3) . . . . ?
C11 C12 C17 C18 0.9(3) . . . . ?
C13 C12 C17 C18 178.8(2) . . . . ?
C11 C12 C17 C16 -176.5(2) . . . . ?
C13 C12 C17 C16 1.3(3) . . . . ?
C16 C17 C18 C19 175.9(2) . . . . ?
C12 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C114 0.5(3) . . . . ?
C17 C18 C19 C110 -179.3(2) . . . . ?
C18 C19 C110 C111 177.9(2) . . . . ?
C114 C19 C110 C111 -1.9(4) . . . . ?
C19 C110 C111 C112 0.2(4) . . . . ?
C110 C111 C112 C113 1.4(4) . . . . ?
C111 C112 C113 C114 -1.3(4) . . . . ?
C12 C11 C114 C113 177.2(2) . . . . ?
C115 C11 C114 C113 -3.0(3) . . . . ?
C12 C11 C114 C19 -1.7(3) . . . . ?
C115 C11 C114 C19 178.14(19) . . . . ?
C112 C113 C114 C11 -179.3(2) . . . . ?
C112 C113 C114 C19 -0.4(3) . . . . ?
C18 C19 C114 C11 1.1(3) . . . . ?
C110 C19 C114 C11 -179.1(2) . . . . ?
C18 C19 C114 C113 -177.8(2) . . . . ?
C110 C19 C114 C113 2.0(3) . . . . ?
C12 C11 C115 O11 94.5(3) . . . . ?
C114 C11 C115 O11 -85.3(3) . . . . ?
C12 C11 C115 O12 -86.3(2) . . . . ?
C114 C11 C115 O12 93.9(2) . . . . ?
C24 C21 C22 N22 177.8(2) . . . . ?
C24 C21 C22 C23 -0.3(3) . . . . ?
N22 C22 C23 N21 -177.1(2) . . . . ?
C21 C22 C23 N21 1.0(3) . . . . ?
C22 C21 C24 C25 -0.6(3) . . . . ?
C21 C24 C25 N21 0.9(3) . . . . ?
C21 C24 C25 Br21 -179.18(17) . . . . ?
C24 C25 N21 C23 -0.2(3) . . . . ?
Br21 C25 N21 C23 179.82(16) . . . . ?
C22 C23 N21 C25 -0.7(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
_geom_hbond_publ_flag
O12 H12 N21 0.84(4) 1.78(4) 2.613(3) 174(3) . yes
N22 H22A O2 0.85(3) 2.31(4) 3.157(4) 174(3) 3_666 yes
N22 H22B O2 0.85(3) 2.44(3) 3.267(3) 165(3) 1_655 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_4
_audit_block_doi                 10.5517/ccdc.csd.cc1j2t6m
_database_code_depnum_ccdc_archive 'CCDC 1402880'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T07:27:38-00:00
_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, H2 O'
_chemical_formula_sum            'C26 H21 N5 O9'
_chemical_formula_weight         547.48

#----------------------------------------------------------------------------#
#                   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                   7.234(2)
_cell_length_b                   9.378(3)
_cell_length_c                   35.927(11)
_cell_angle_alpha                89.798(6)
_cell_angle_beta                 88.075(6)
_cell_angle_gamma                87.452(6)
_cell_volume                     2433.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6951
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28.21
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9954
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.995

#----------------------------------------------------------------------------#
#                   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  0.0506
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_number            24395
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.836
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             8989
_reflns_number_gt                6031
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0493P)²+4.7819P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8989
_refine_ls_number_parameters     761
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.168
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.5
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   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
O01 O -0.2108(4) 0.6635(3) 0.25425(9) 0.0328(7) Uani 1 1 d . . . . .
O02 O 1.5157(5) -0.1124(4) 0.27298(10) 0.0450(9) Uani 1 1 d . . . . .
H01A H -0.160(6) 0.675(5) 0.2299(13) 0.038(12) Uiso 1 1 d . . . . .
H02B H 1.441(7) -0.154(5) 0.2857(13) 0.037(14) Uiso 1 1 d . . . . .
H02A H 1.603(8) -0.175(6) 0.2636(14) 0.064(17) Uiso 1 1 d . . . . .
H01B H -0.140(7) 0.699(6) 0.2714(15) 0.060(17) Uiso 1 1 d . . . . .
C1 C 0.4737(5) 0.7714(5) 0.06246(11) 0.0285(9) Uani 1 1 d . . . . .
C2 C 0.5506(5) 0.6352(5) 0.06666(11) 0.0300(9) Uani 1 1 d . . . . .
H2 H 0.569645 0.572078 0.046139 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5982(5) 0.5958(4) 0.10193(11) 0.0273(9) Uani 1 1 d . . . . .
C4 C 0.5774(5) 0.6849(4) 0.13214(11) 0.0283(9) Uani 1 1 d . . . . .
H4 H 0.613956 0.655187 0.156211 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5010(5) 0.8195(4) 0.12583(11) 0.0277(9) Uani 1 1 d . . . . .
C6 C 0.4467(5) 0.8652(4) 0.09164(11) 0.0301(9) Uani 1 1 d . . . . .
H6 H 0.392401 0.958154 0.088143 0.036 Uiso 1 1 calc R U . . .
N1 N 0.4198(5) 0.8194(5) 0.02544(10) 0.0430(10) Uani 1 1 d . . . . .
N2 N 0.6739(5) 0.4489(4) 0.10758(11) 0.0348(9) Uani 1 1 d . . . . .
N3 N 0.4782(5) 0.9190(4) 0.15698(10) 0.0359(9) Uani 1 1 d . . . . .
O1 O 0.3485(5) 0.9395(4) 0.02244(9) 0.0546(9) Uani 1 1 d . . . . .
O2 O 0.4452(5) 0.7354(4) -0.00034(9) 0.0614(10) Uani 1 1 d . . . . .
O3 O 0.7198(5) 0.3814(4) 0.07966(10) 0.0558(9) Uani 1 1 d . . . . .
O4 O 0.6837(4) 0.4054(3) 0.13936(9) 0.0446(8) Uani 1 1 d . . . . .
O5 O 0.5567(5) 0.8918(3) 0.18544(9) 0.0455(8) Uani 1 1 d . . . . .
O6 O 0.3778(5) 1.0267(3) 0.15247(10) 0.0540(9) Uani 1 1 d . . . . .
C11 C 0.0496(5) 0.6948(4) 0.12540(10) 0.0222(8) Uani 1 1 d . . . . .
C12 C -0.0154(5) 0.8171(4) 0.10623(10) 0.0236(8) Uani 1 1 d . . . . .
C13 C -0.0707(5) 0.9459(4) 0.12508(12) 0.0299(9) Uani 1 1 d . . . . .
H13 H -0.061049 0.950842 0.151343 0.036 Uiso 1 1 calc R U . . .
C14 C -0.1370(6) 1.0617(5) 0.10622(13) 0.0376(11) Uani 1 1 d . . . . .
H14 H -0.174543 1.146369 0.119381 0.045 Uiso 1 1 calc R U . . .
C15 C -0.1507(6) 1.0572(5) 0.06719(13) 0.0391(11) Uani 1 1 d . . . . .
H15 H -0.195966 1.139268 0.05421 0.047 Uiso 1 1 calc R U . . .
C16 C -0.0996(6) 0.9368(5) 0.04805(12) 0.0350(10) Uani 1 1 d . . . . .
H16 H -0.112385 0.934492 0.021829 0.042 Uiso 1 1 calc R U . . .
C17 C -0.0268(5) 0.8132(4) 0.06686(11) 0.0264(9) Uani 1 1 d . . . . .
C18 C 0.0325(5) 0.6899(5) 0.04755(11) 0.0302(9) Uani 1 1 d . . . . .
H18 H 0.026714 0.688429 0.021179 0.036 Uiso 1 1 calc R U . . .
C19 C 0.0995(5) 0.5696(4) 0.06604(11) 0.0277(9) Uani 1 1 d . . . . .
C110 C 0.1669(6) 0.4442(5) 0.04657(13) 0.0398(11) Uani 1 1 d . . . . .
H110 H 0.166481 0.443008 0.020129 0.048 Uiso 1 1 calc R U . . .
C111 C 0.2316(7) 0.3267(5) 0.06500(14) 0.0454(12) Uani 1 1 d . . . . .
H111 H 0.276347 0.244768 0.05146 0.054 Uiso 1 1 calc R U . . .
C112 C 0.2323(6) 0.3262(5) 0.10430(13) 0.0424(11) Uani 1 1 d . . . . .
H112 H 0.275977 0.243308 0.117154 0.051 Uiso 1 1 calc R U . . .
C113 C 0.1707(6) 0.4441(4) 0.12383(12) 0.0327(10) Uani 1 1 d . . . . .
H113 H 0.171734 0.441911 0.150261 0.039 Uiso 1 1 calc R U . . .
C114 C 0.1048(5) 0.5703(4) 0.10566(11) 0.0253(9) Uani 1 1 d . . . . .
C115 C 0.0555(5) 0.6971(4) 0.16718(11) 0.0249(9) Uani 1 1 d . . . . .
O11 O 0.1904(4) 0.7532(3) 0.18133(8) 0.0383(7) Uani 1 1 d . . . . .
O12 O -0.0764(4) 0.6437(3) 0.18482(8) 0.0373(7) Uani 1 1 d . . . . .
C21 C 0.9285(6) 0.3272(5) 0.22077(12) 0.0342(10) Uani 1 1 d . . . . .
H21 H 0.933023 0.393669 0.20077 0.041 Uiso 1 1 calc R U . . .
C22 C 0.9922(6) 0.1917(5) 0.21502(11) 0.0338(10) Uani 1 1 d . . . . .
H22 H 1.040028 0.163342 0.191103 0.041 Uiso 1 1 calc R U . . .
C23 C 0.9881(5) 0.0920(4) 0.24442(11) 0.0266(9) Uani 1 1 d . . . . .
C24 C 0.9099(5) 0.1413(4) 0.27864(11) 0.0288(9) Uani 1 1 d . . . . .
H24 H 0.900038 0.077617 0.299157 0.035 Uiso 1 1 calc R U . . .
C25 C 0.8488(6) 0.2789(5) 0.28244(12) 0.0323(10) Uani 1 1 d . . . . .
H25 H 0.797809 0.310991 0.305811 0.039 Uiso 1 1 calc R U . . .
N21 N 0.8587(5) 0.3705(4) 0.25416(10) 0.0341(9) Uani 1 1 d . . . . .
N22 N 1.0538(5) -0.0432(4) 0.24100(11) 0.0342(9) Uani 1 1 d . . . . .
H21A H 0.826(6) 0.461(5) 0.2571(12) 0.042(14) Uiso 1 1 d . . . . .
H22B H 1.106(6) -0.078(4) 0.2189(12) 0.031(12) Uiso 1 1 d . . . . .
H22A H 1.045(7) -0.091(5) 0.2640(14) 0.051(15) Uiso 1 1 d . . . . .
C31 C 0.5483(5) 0.6709(4) 0.38123(10) 0.0221(8) Uani 1 1 d . . . . .
C32 C 0.4905(5) 0.6436(4) 0.41730(11) 0.0254(9) Uani 1 1 d . . . . .
H32 H 0.444234 0.553823 0.424293 0.03 Uiso 1 1 calc R U . . .
C33 C 0.5023(5) 0.7509(4) 0.44279(10) 0.0270(9) Uani 1 1 d . . . . .
C34 C 0.5651(5) 0.8837(4) 0.43349(11) 0.0285(9) Uani 1 1 d . . . . .
H34 H 0.573895 0.956228 0.451668 0.034 Uiso 1 1 calc R U . . .
C35 C 0.6141(5) 0.9062(4) 0.39676(11) 0.0251(9) Uani 1 1 d . . . . .
C36 C 0.6080(5) 0.8027(4) 0.36981(11) 0.0237(8) Uani 1 1 d . . . . .
H36 H 0.643134 0.820906 0.344578 0.028 Uiso 1 1 calc R U . . .
N31 N 0.5460(5) 0.5560(4) 0.35396(9) 0.0290(8) Uani 1 1 d . . . . .
N32 N 0.4433(6) 0.7250(5) 0.48139(10) 0.0425(10) Uani 1 1 d . . . . .
N33 N 0.6736(5) 1.0478(4) 0.38607(10) 0.0330(8) Uani 1 1 d . . . . .
O31 O 0.6262(4) 0.5713(3) 0.32409(8) 0.0343(7) Uani 1 1 d . . . . .
O32 O 0.4677(5) 0.4479(3) 0.36333(9) 0.0486(9) Uani 1 1 d . . . . .
O33 O 0.3684(5) 0.6139(4) 0.48845(9) 0.0587(10) Uani 1 1 d . . . . .
O34 O 0.4662(7) 0.8159(5) 0.50422(10) 0.0866(15) Uani 1 1 d . . . . .
O35 O 0.7064(5) 1.1292(3) 0.41102(9) 0.0527(9) Uani 1 1 d . . . . .
O36 O 0.6847(5) 1.0758(3) 0.35303(9) 0.0459(8) Uani 1 1 d . . . . .
C41 C 1.0806(5) 0.7813(4) 0.37108(10) 0.0203(8) Uani 1 1 d . . . . .
C42 C 1.0195(5) 0.6642(4) 0.39127(10) 0.0220(8) Uani 1 1 d . . . . .
C43 C 0.9816(5) 0.5328(4) 0.37380(11) 0.0255(9) Uani 1 1 d . . . . .
H43 H 1.002411 0.523343 0.347658 0.031 Uiso 1 1 calc R U . . .
C44 C 0.9168(5) 0.4215(4) 0.39348(12) 0.0302(9) Uani 1 1 d . . . . .
H44 H 0.893891 0.334901 0.381157 0.036 Uiso 1 1 calc R U . . .
C45 C 0.8831(5) 0.4335(5) 0.43226(12) 0.0335(10) Uani 1 1 d . . . . .
H45 H 0.834147 0.355864 0.44585 0.04 Uiso 1 1 calc R U . . .
C46 C 0.9203(5) 0.5558(5) 0.45030(11) 0.0318(10) Uani 1 1 d . . . . .
H46 H 0.898877 0.561907 0.476491 0.038 Uiso 1 1 calc R U . . .
C47 C 0.9905(5) 0.6743(4) 0.43057(10) 0.0242(8) Uani 1 1 d . . . . .
C48 C 1.0302(5) 0.8008(4) 0.44841(11) 0.0288(9) Uani 1 1 d . . . . .
H48 H 1.011802 0.807474 0.474664 0.035 Uiso 1 1 calc R U . . .
C49 C 1.0959(5) 0.9171(4) 0.42887(11) 0.0282(9) Uani 1 1 d . . . . .
C410 C 1.1480(6) 1.0425(5) 0.44690(12) 0.0347(10) Uani 1 1 d . . . . .
H410 H 1.135523 1.049004 0.473253 0.042 Uiso 1 1 calc R U . . .
C411 C 1.2144(6) 1.1522(5) 0.42746(13) 0.0403(11) Uani 1 1 d . . . . .
H411 H 1.249206 1.234807 0.440232 0.048 Uiso 1 1 calc R U . . .
C412 C 1.2336(6) 1.1467(4) 0.38830(13) 0.0377(11) Uani 1 1 d . . . . .
H412 H 1.279083 1.225964 0.374854 0.045 Uiso 1 1 calc R U . . .
C413 C 1.1871(5) 1.0286(4) 0.36988(12) 0.0300(9) Uani 1 1 d . . . . .
H413 H 1.198584 1.026416 0.343463 0.036 Uiso 1 1 calc R U . . .
C414 C 1.1211(5) 0.9074(4) 0.38940(10) 0.0236(8) Uani 1 1 d . . . . .
C415 C 1.1061(5) 0.7712(4) 0.32951(11) 0.0242(9) Uani 1 1 d . . . . .
O41 O 1.2624(4) 0.7279(3) 0.31705(8) 0.0380(7) Uani 1 1 d . . . . .
O42 O 0.9713(4) 0.8076(3) 0.31011(7) 0.0331(7) Uani 1 1 d . . . . .
C51 C 1.4707(6) 0.2384(5) 0.21630(14) 0.0435(12) Uani 1 1 d . . . . .
H51 H 1.517366 0.191237 0.194348 0.052 Uiso 1 1 calc R U . . .
C52 C 1.4202(6) 0.3803(5) 0.21477(12) 0.0381(11) Uani 1 1 d . . . . .
H52 H 1.432207 0.431303 0.191993 0.046 Uiso 1 1 calc R U . . .
C53 C 1.3502(5) 0.4504(4) 0.24723(11) 0.0288(9) Uani 1 1 d . . . . .
C54 C 1.3431(6) 0.3710(5) 0.28025(12) 0.0334(10) Uani 1 1 d . . . . .
H54 H 1.301764 0.415385 0.302941 0.04 Uiso 1 1 calc R U . . .
C55 C 1.3957(6) 0.2301(5) 0.27971(14) 0.0412(11) Uani 1 1 d . . . . .
H55 H 1.389988 0.17649 0.302169 0.049 Uiso 1 1 calc R U . . .
N51 N 1.4559(5) 0.1649(4) 0.24788(13) 0.0442(10) Uani 1 1 d . . . . .
N52 N 1.2960(5) 0.5873(4) 0.24657(11) 0.0370(9) Uani 1 1 d . . . . .
H51A H 1.488(7) 0.061(6) 0.2528(14) 0.067(16) Uiso 1 1 d . . . . .
H52A H 1.264(7) 0.633(5) 0.2694(14) 0.055(15) Uiso 1 1 d . . . . .
H52B H 1.295(8) 0.650(6) 0.2231(16) 0.078(18) 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
O01 H01A 0.95(5) . ?
O01 H01B 0.89(5) . ?
O02 H02B 0.81(5) . ?
O02 H02A 0.90(6) . ?
C1 C6 1.375(6) . ?
C1 C2 1.380(6) . ?
C1 N1 1.462(5) . ?
C2 C3 1.369(6) . ?
C2 H2 0.95 . ?
C3 C4 1.372(5) . ?
C3 N2 1.476(5) . ?
C4 C5 1.377(6) . ?
C4 H4 0.95 . ?
C5 C6 1.364(6) . ?
C5 N3 1.460(5) . ?
C6 H6 0.95 . ?
N1 O2 1.222(5) . ?
N1 O1 1.224(5) . ?
N2 O4 1.214(5) . ?
N2 O3 1.217(5) . ?
N3 O5 1.207(4) . ?
N3 O6 1.231(5) . ?
C11 C114 1.404(5) . ?
C11 C12 1.407(5) . ?
C11 C115 1.503(5) . ?
C12 C13 1.421(5) . ?
C12 C17 1.420(5) . ?
C13 C14 1.357(6) . ?
C13 H13 0.95 . ?
C14 C15 1.410(6) . ?
C14 H14 0.95 . ?
C15 C16 1.355(6) . ?
C15 H15 0.95 . ?
C16 C17 1.429(6) . ?
C16 H16 0.95 . ?
C17 C18 1.394(6) . ?
C18 C19 1.385(6) . ?
C18 H18 0.95 . ?
C19 C110 1.430(6) . ?
C19 C114 1.425(5) . ?
C110 C111 1.356(7) . ?
C110 H110 0.95 . ?
C111 C112 1.412(7) . ?
C111 H111 0.95 . ?
C112 C113 1.362(6) . ?
C112 H112 0.95 . ?
C113 C114 1.421(6) . ?
C113 H113 0.95 . ?
C115 O12 1.250(5) . ?
C115 O11 1.253(5) . ?
C21 N21 1.343(5) . ?
C21 C22 1.347(6) . ?
C21 H21 0.95 . ?
C22 C23 1.409(6) . ?
C22 H22 0.95 . ?
C23 N22 1.338(5) . ?
C23 C24 1.407(5) . ?
C24 C25 1.351(6) . ?
C24 H24 0.95 . ?
C25 N21 1.330(6) . ?
C25 H25 0.95 . ?
N21 H21A 0.87(5) . ?
N22 H22B 0.92(4) . ?
N22 H22A 0.94(5) . ?
C31 C32 1.375(5) . ?
C31 C36 1.384(5) . ?
C31 N31 1.460(5) . ?
C32 C33 1.370(5) . ?
C32 H32 0.95 . ?
C33 C34 1.381(6) . ?
C33 N32 1.460(5) . ?
C34 C35 1.373(5) . ?
C34 H34 0.95 . ?
C35 C36 1.376(5) . ?
C35 N33 1.460(5) . ?
C36 H36 0.95 . ?
N31 O31 1.214(4) . ?
N31 O32 1.224(4) . ?
N32 O34 1.205(5) . ?
N32 O33 1.218(5) . ?
N33 O35 1.216(4) . ?
N33 O36 1.216(4) . ?
C41 C414 1.402(5) . ?
C41 C42 1.395(5) . ?
C41 C415 1.502(5) . ?
C42 C47 1.424(5) . ?
C42 C43 1.426(5) . ?
C43 C44 1.351(5) . ?
C43 H43 0.95 . ?
C44 C45 1.410(6) . ?
C44 H44 0.95 . ?
C45 C46 1.361(6) . ?
C45 H45 0.95 . ?
C46 C47 1.420(6) . ?
C46 H46 0.95 . ?
C47 C48 1.396(6) . ?
C48 C49 1.388(6) . ?
C48 H48 0.95 . ?
C49 C410 1.417(6) . ?
C49 C414 1.426(5) . ?
C410 C411 1.339(6) . ?
C410 H410 0.95 . ?
C411 C412 1.410(6) . ?
C411 H411 0.95 . ?
C412 C413 1.354(6) . ?
C412 H412 0.95 . ?
C413 C414 1.425(5) . ?
C413 H413 0.95 . ?
C415 O42 1.252(5) . ?
C415 O41 1.253(5) . ?
C51 N51 1.329(6) . ?
C51 C52 1.365(7) . ?
C51 H51 0.95 . ?
C52 C53 1.409(6) . ?
C52 H52 0.95 . ?
C53 N52 1.326(5) . ?
C53 C54 1.399(6) . ?
C54 C55 1.359(6) . ?
C54 H54 0.95 . ?
C55 N51 1.348(6) . ?
C55 H55 0.95 . ?
N51 H51A 1.01(6) . ?
N52 H52A 0.95(5) . ?
N52 H52B 1.03(6) . ?

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
H01A O01 H01B 112(4) . . ?
H02B O02 H02A 110(5) . . ?
C6 C1 C2 122.8(4) . . ?
C6 C1 N1 118.2(4) . . ?
C2 C1 N1 119.1(4) . . ?
C3 C2 C1 116.6(4) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C2 C3 C4 123.5(4) . . ?
C2 C3 N2 117.9(4) . . ?
C4 C3 N2 118.6(4) . . ?
C3 C4 C5 116.7(4) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C6 C5 C4 123.0(4) . . ?
C6 C5 N3 118.2(4) . . ?
C4 C5 N3 118.8(4) . . ?
C5 C6 C1 117.4(4) . . ?
C5 C6 H6 121.3 . . ?
C1 C6 H6 121.3 . . ?
O2 N1 O1 124.3(4) . . ?
O2 N1 C1 117.6(4) . . ?
O1 N1 C1 118.0(4) . . ?
O4 N2 O3 125.7(4) . . ?
O4 N2 C3 117.7(3) . . ?
O3 N2 C3 116.5(4) . . ?
O5 N3 O6 123.8(4) . . ?
O5 N3 C5 119.1(4) . . ?
O6 N3 C5 117.1(4) . . ?
C114 C11 C12 120.2(3) . . ?
C114 C11 C115 120.2(3) . . ?
C12 C11 C115 119.7(3) . . ?
C11 C12 C13 122.0(3) . . ?
C11 C12 C17 119.5(3) . . ?
C13 C12 C17 118.5(3) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C12 119.7(4) . . ?
C18 C17 C16 121.6(4) . . ?
C12 C17 C16 118.7(4) . . ?
C19 C18 C17 121.3(4) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C110 122.0(4) . . ?
C18 C19 C114 119.6(4) . . ?
C110 C19 C114 118.4(4) . . ?
C111 C110 C19 121.4(4) . . ?
C111 C110 H110 119.3 . . ?
C19 C110 H110 119.3 . . ?
C110 C111 C112 120.1(4) . . ?
C110 C111 H111 120 . . ?
C112 C111 H111 120 . . ?
C113 C112 C111 120.2(4) . . ?
C113 C112 H112 119.9 . . ?
C111 C112 H112 119.9 . . ?
C112 C113 C114 121.6(4) . . ?
C112 C113 H113 119.2 . . ?
C114 C113 H113 119.2 . . ?
C11 C114 C113 122.1(4) . . ?
C11 C114 C19 119.7(4) . . ?
C113 C114 C19 118.2(4) . . ?
O12 C115 O11 125.6(4) . . ?
O12 C115 C11 116.8(3) . . ?
O11 C115 C11 117.5(3) . . ?
N21 C21 C22 121.4(4) . . ?
N21 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
N22 C23 C24 120.3(4) . . ?
N22 C23 C22 123.3(4) . . ?
C24 C23 C22 116.4(4) . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
N21 C25 C24 121.4(4) . . ?
N21 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 N21 C21 120.4(4) . . ?
C25 N21 H21A 121(3) . . ?
C21 N21 H21A 118(3) . . ?
C23 N22 H22B 122(3) . . ?
C23 N22 H22A 111(3) . . ?
H22B N22 H22A 127(4) . . ?
C32 C31 C36 122.6(3) . . ?
C32 C31 N31 118.5(3) . . ?
C36 C31 N31 118.9(3) . . ?
C33 C32 C31 117.4(4) . . ?
C33 C32 H32 121.3 . . ?
C31 C32 H32 121.3 . . ?
C32 C33 C34 122.9(4) . . ?
C32 C33 N32 118.8(4) . . ?
C34 C33 N32 118.3(4) . . ?
C35 C34 C33 116.9(4) . . ?
C35 C34 H34 121.5 . . ?
C33 C34 H34 121.5 . . ?
C34 C35 C36 123.3(4) . . ?
C34 C35 N33 117.8(3) . . ?
C36 C35 N33 119.0(3) . . ?
C35 C36 C31 116.8(4) . . ?
C35 C36 H36 121.6 . . ?
C31 C36 H36 121.6 . . ?
O31 N31 O32 124.1(3) . . ?
O31 N31 C31 118.5(3) . . ?
O32 N31 C31 117.3(3) . . ?
O34 N32 O33 123.7(4) . . ?
O34 N32 C33 118.5(4) . . ?
O33 N32 C33 117.7(4) . . ?
O35 N33 O36 125.1(4) . . ?
O35 N33 C35 117.3(4) . . ?
O36 N33 C35 117.7(3) . . ?
C414 C41 C42 120.5(3) . . ?
C414 C41 C415 119.9(3) . . ?
C42 C41 C415 119.6(3) . . ?
C41 C42 C47 119.9(3) . . ?
C41 C42 C43 122.2(3) . . ?
C47 C42 C43 117.9(3) . . ?
C44 C43 C42 121.7(4) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 120.2(4) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C46 C45 C44 120.3(4) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C45 C46 C47 121.0(4) . . ?
C45 C46 H46 119.5 . . ?
C47 C46 H46 119.5 . . ?
C48 C47 C46 122.2(4) . . ?
C48 C47 C42 119.0(4) . . ?
C46 C47 C42 118.8(4) . . ?
C49 C48 C47 121.8(4) . . ?
C49 C48 H48 119.1 . . ?
C47 C48 H48 119.1 . . ?
C48 C49 C410 122.3(4) . . ?
C48 C49 C414 119.0(4) . . ?
C410 C49 C414 118.6(4) . . ?
C411 C410 C49 121.2(4) . . ?
C411 C410 H410 119.4 . . ?
C49 C410 H410 119.4 . . ?
C410 C411 C412 121.0(4) . . ?
C410 C411 H411 119.5 . . ?
C412 C411 H411 119.5 . . ?
C413 C412 C411 120.0(4) . . ?
C413 C412 H412 120 . . ?
C411 C412 H412 120 . . ?
C412 C413 C414 121.2(4) . . ?
C412 C413 H413 119.4 . . ?
C414 C413 H413 119.4 . . ?
C41 C414 C49 119.8(3) . . ?
C41 C414 C413 122.2(4) . . ?
C49 C414 C413 118.0(4) . . ?
O42 C415 O41 125.3(4) . . ?
O42 C415 C41 117.8(3) . . ?
O41 C415 C41 116.9(3) . . ?
N51 C51 C52 121.3(4) . . ?
N51 C51 H51 119.3 . . ?
C52 C51 H51 119.3 . . ?
C51 C52 C53 119.5(4) . . ?
C51 C52 H52 120.2 . . ?
C53 C52 H52 120.2 . . ?
N52 C53 C54 121.3(4) . . ?
N52 C53 C52 121.1(4) . . ?
C54 C53 C52 117.6(4) . . ?
C55 C54 C53 119.7(4) . . ?
C55 C54 H54 120.2 . . ?
C53 C54 H54 120.2 . . ?
N51 C55 C54 121.2(4) . . ?
N51 C55 H55 119.4 . . ?
C54 C55 H55 119.4 . . ?
C51 N51 C55 120.6(4) . . ?
C51 N51 H51A 129(3) . . ?
C55 N51 H51A 110(3) . . ?
C53 N52 H52A 118(3) . . ?
C53 N52 H52B 125(3) . . ?
H52A N52 H52B 117(4) . . ?

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 0.7(6) . . . . ?
N1 C1 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C4 -1.7(6) . . . . ?
C1 C2 C3 N2 177.6(3) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
N2 C3 C4 C5 -178.0(3) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C3 C4 C5 N3 -179.2(3) . . . . ?
C4 C5 C6 C1 -1.1(6) . . . . ?
N3 C5 C6 C1 178.3(3) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
N1 C1 C6 C5 -178.8(4) . . . . ?
C6 C1 N1 O2 179.7(4) . . . . ?
C2 C1 N1 O2 0.3(6) . . . . ?
C6 C1 N1 O1 -2.0(6) . . . . ?
C2 C1 N1 O1 178.6(4) . . . . ?
C2 C3 N2 O4 -166.6(4) . . . . ?
C4 C3 N2 O4 12.8(5) . . . . ?
C2 C3 N2 O3 12.8(5) . . . . ?
C4 C3 N2 O3 -167.9(4) . . . . ?
C6 C5 N3 O5 -165.7(4) . . . . ?
C4 C5 N3 O5 13.7(6) . . . . ?
C6 C5 N3 O6 14.6(5) . . . . ?
C4 C5 N3 O6 -166.0(4) . . . . ?
C114 C11 C12 C13 -179.3(4) . . . . ?
C115 C11 C12 C13 2.1(5) . . . . ?
C114 C11 C12 C17 0.7(5) . . . . ?
C115 C11 C12 C17 -177.9(3) . . . . ?
C11 C12 C13 C14 -178.5(4) . . . . ?
C17 C12 C13 C14 1.5(6) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C14 C15 C16 C17 -1.5(6) . . . . ?
C11 C12 C17 C18 -2.2(5) . . . . ?
C13 C12 C17 C18 177.8(4) . . . . ?
C11 C12 C17 C16 177.7(4) . . . . ?
C13 C12 C17 C16 -2.3(5) . . . . ?
C15 C16 C17 C18 -177.8(4) . . . . ?
C15 C16 C17 C12 2.4(6) . . . . ?
C12 C17 C18 C19 1.2(6) . . . . ?
C16 C17 C18 C19 -178.7(4) . . . . ?
C17 C18 C19 C110 -177.7(4) . . . . ?
C17 C18 C19 C114 1.3(6) . . . . ?
C18 C19 C110 C111 -179.7(4) . . . . ?
C114 C19 C110 C111 1.3(6) . . . . ?
C19 C110 C111 C112 0.4(7) . . . . ?
C110 C111 C112 C113 -0.9(7) . . . . ?
C111 C112 C113 C114 -0.2(7) . . . . ?
C12 C11 C114 C113 -179.7(4) . . . . ?
C115 C11 C114 C113 -1.2(5) . . . . ?
C12 C11 C114 C19 1.7(5) . . . . ?
C115 C11 C114 C19 -179.7(3) . . . . ?
C112 C113 C114 C11 -176.8(4) . . . . ?
C112 C113 C114 C19 1.8(6) . . . . ?
C18 C19 C114 C11 -2.7(5) . . . . ?
C110 C19 C114 C11 176.3(4) . . . . ?
C18 C19 C114 C113 178.7(4) . . . . ?
C110 C19 C114 C113 -2.3(5) . . . . ?
C114 C11 C115 O12 -80.5(5) . . . . ?
C12 C11 C115 O12 98.1(4) . . . . ?
C114 C11 C115 O11 100.1(4) . . . . ?
C12 C11 C115 O11 -81.3(5) . . . . ?
N21 C21 C22 C23 -0.5(6) . . . . ?
C21 C22 C23 N22 -178.0(4) . . . . ?
C21 C22 C23 C24 1.9(6) . . . . ?
N22 C23 C24 C25 177.9(4) . . . . ?
C22 C23 C24 C25 -2.0(6) . . . . ?
C23 C24 C25 N21 0.8(6) . . . . ?
C24 C25 N21 C21 0.7(6) . . . . ?
C22 C21 N21 C25 -0.8(6) . . . . ?
C36 C31 C32 C33 -3.2(6) . . . . ?
N31 C31 C32 C33 176.9(3) . . . . ?
C31 C32 C33 C34 1.4(6) . . . . ?
C31 C32 C33 N32 -179.6(3) . . . . ?
C32 C33 C34 C35 0.9(6) . . . . ?
N32 C33 C34 C35 -178.0(3) . . . . ?
C33 C34 C35 C36 -1.8(6) . . . . ?
C33 C34 C35 N33 177.6(3) . . . . ?
C34 C35 C36 C31 0.2(6) . . . . ?
N33 C35 C36 C31 -179.1(3) . . . . ?
C32 C31 C36 C35 2.4(6) . . . . ?
N31 C31 C36 C35 -177.7(3) . . . . ?
C32 C31 N31 O31 -167.2(3) . . . . ?
C36 C31 N31 O31 12.9(5) . . . . ?
C32 C31 N31 O32 10.4(5) . . . . ?
C36 C31 N31 O32 -169.5(4) . . . . ?
C32 C33 N32 O34 174.8(4) . . . . ?
C34 C33 N32 O34 -6.2(6) . . . . ?
C32 C33 N32 O33 -7.4(6) . . . . ?
C34 C33 N32 O33 171.6(4) . . . . ?
C34 C35 N33 O35 12.3(5) . . . . ?
C36 C35 N33 O35 -168.3(4) . . . . ?
C34 C35 N33 O36 -167.0(4) . . . . ?
C36 C35 N33 O36 12.4(5) . . . . ?
C414 C41 C42 C47 2.6(5) . . . . ?
C415 C41 C42 C47 -178.4(3) . . . . ?
C414 C41 C42 C43 -178.3(3) . . . . ?
C415 C41 C42 C43 0.7(5) . . . . ?
C41 C42 C43 C44 -177.9(4) . . . . ?
C47 C42 C43 C44 1.2(5) . . . . ?
C42 C43 C44 C45 0.6(6) . . . . ?
C43 C44 C45 C46 -1.8(6) . . . . ?
C44 C45 C46 C47 1.1(6) . . . . ?
C45 C46 C47 C48 -179.9(4) . . . . ?
C45 C46 C47 C42 0.8(6) . . . . ?
C41 C42 C47 C48 -2.1(5) . . . . ?
C43 C42 C47 C48 178.7(3) . . . . ?
C41 C42 C47 C46 177.2(4) . . . . ?
C43 C42 C47 C46 -2.0(5) . . . . ?
C46 C47 C48 C49 -178.9(4) . . . . ?
C42 C47 C48 C49 0.4(6) . . . . ?
C47 C48 C49 C410 -175.8(4) . . . . ?
C47 C48 C49 C414 0.8(6) . . . . ?
C48 C49 C410 C411 178.6(4) . . . . ?
C414 C49 C410 C411 2.0(6) . . . . ?
C49 C410 C411 C412 0.5(7) . . . . ?
C410 C411 C412 C413 -1.0(6) . . . . ?
C411 C412 C413 C414 -1.0(6) . . . . ?
C42 C41 C414 C49 -1.4(5) . . . . ?
C415 C41 C414 C49 179.7(3) . . . . ?
C42 C41 C414 C413 178.9(4) . . . . ?
C415 C41 C414 C413 -0.1(5) . . . . ?
C48 C49 C414 C41 -0.3(5) . . . . ?
C410 C49 C414 C41 176.4(4) . . . . ?
C48 C49 C414 C413 179.4(4) . . . . ?
C410 C49 C414 C413 -3.8(5) . . . . ?
C412 C413 C414 C41 -176.8(4) . . . . ?
C412 C413 C414 C49 3.4(6) . . . . ?
C414 C41 C415 O42 -90.4(4) . . . . ?
C42 C41 C415 O42 90.6(4) . . . . ?
C414 C41 C415 O41 89.0(4) . . . . ?
C42 C41 C415 O41 -90.0(4) . . . . ?
N51 C51 C52 C53 -0.3(6) . . . . ?
C51 C52 C53 N52 -178.5(4) . . . . ?
C51 C52 C53 C54 2.6(6) . . . . ?
N52 C53 C54 C55 178.5(4) . . . . ?
C52 C53 C54 C55 -2.7(6) . . . . ?
C53 C54 C55 N51 0.4(6) . . . . ?
C52 C51 N51 C55 -2.1(7) . . . . ?
C54 C55 N51 C51 2.1(6) . . . . ?

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
O01 H01A O12 0.95(5) 1.73(5) 2.651(4) 163(4) . yes
O02 H02B O41 0.81(5) 2.05(5) 2.854(5) 176(5) 1_545 yes
O02 H02A O01 0.90(6) 2.01(6) 2.887(5) 167(5) 1_745 yes
O01 H01B O42 0.89(5) 1.94(6) 2.818(4) 167(5) 1_455 yes
N21 H21A O01 0.87(5) 1.91(5) 2.772(5) 168(4) 1_655 yes
N22 H22B O11 0.92(4) 2.14(4) 2.990(5) 153(4) 1_645 yes
N22 H22A O42 0.94(5) 1.98(5) 2.904(5) 168(4) 1_545 yes
N51 H51A O02 1.01(6) 1.78(6) 2.770(5) 165(5) . yes
N52 H52A O41 0.95(5) 1.93(5) 2.857(5) 166(4) . yes
N52 H52B O11 1.03(6) 1.94(6) 2.913(5) 157(5) 1_655 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_3
_audit_block_doi                 10.5517/ccdc.csd.cc1j2t5l
_database_code_depnum_ccdc_archive 'CCDC 1402879'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T07:07:16-00:00
_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 H10 O2, C15 H9 O2, 2(C6 H3 N3 O6), C5 H7 N2'
_chemical_formula_sum            'C47 H32 N8 O16'
_chemical_formula_weight         964.8

#----------------------------------------------------------------------------#
#                   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                   13.6779(11)
_cell_length_b                   18.3499(14)
_cell_length_c                   17.2493(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.983(3)
_cell_angle_gamma                90
_cell_volume                     4218.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      28.08
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       cuboid
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_T_max  0.9803
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.98

#----------------------------------------------------------------------------#
#                   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  0.0352
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_number            44511
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             7826
_reflns_number_gt                6148
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0917P)²+2.0133P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7826
_refine_ls_number_parameters     649
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.155
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   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 0.59744(14) 0.20614(12) 0.29323(12) 0.0313(4) Uani 1 1 d . . . . .
C2 C 0.61197(14) 0.20205(11) 0.37495(12) 0.0304(4) Uani 1 1 d . . . . .
H2 H 0.616757 0.156424 0.401577 0.036 Uiso 1 1 calc R U . . .
C3 C 0.61928(14) 0.26705(11) 0.41653(11) 0.0289(4) Uani 1 1 d . . . . .
C4 C 0.61318(14) 0.33399(11) 0.37928(12) 0.0308(4) Uani 1 1 d . . . . .
H4 H 0.618288 0.378148 0.408657 0.037 Uiso 1 1 calc R U . . .
C5 C 0.59937(14) 0.33404(12) 0.29768(12) 0.0329(5) Uani 1 1 d . . . . .
C6 C 0.59060(14) 0.27132(12) 0.25223(12) 0.0339(5) Uani 1 1 d . . . . .
H6 H 0.580442 0.272938 0.195933 0.041 Uiso 1 1 calc R U . . .
N1 N 0.58884(14) 0.13751(11) 0.24730(11) 0.0402(4) Uani 1 1 d . . . . .
N2 N 0.63297(13) 0.26541(10) 0.50359(10) 0.0328(4) Uani 1 1 d . . . . .
N3 N 0.59541(15) 0.40508(11) 0.25750(11) 0.0433(5) Uani 1 1 d . . . . .
O1 O 0.56701(14) 0.14172(11) 0.17514(9) 0.0558(5) Uani 1 1 d . . . . .
O2 O 0.60508(15) 0.08062(10) 0.28497(10) 0.0539(5) Uani 1 1 d . . . . .
O3 O 0.61773(12) 0.20747(9) 0.53437(9) 0.0413(4) Uani 1 1 d . . . . .
O4 O 0.65661(14) 0.32175(9) 0.53991(9) 0.0490(4) Uani 1 1 d . . . . .
O5 O 0.57900(17) 0.45899(10) 0.29424(11) 0.0633(5) Uani 1 1 d . . . . .
O6 O 0.61133(14) 0.40620(10) 0.19051(10) 0.0558(5) Uani 1 1 d . . . . .
C11 C 0.88668(13) 0.26416(11) 0.43690(11) 0.0265(4) Uani 1 1 d . . . . .
C12 C 0.87959(14) 0.34054(11) 0.43813(12) 0.0309(4) Uani 1 1 d . . . . .
C13 C 0.89360(17) 0.38149(12) 0.50992(15) 0.0421(5) Uani 1 1 d . . . . .
H13 H 0.909 0.357 0.559706 0.05 Uiso 1 1 calc R U . . .
C14 C 0.8852(2) 0.45517(14) 0.5078(2) 0.0601(7) Uani 1 1 d . . . . .
H14 H 0.893586 0.481542 0.55626 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8641(2) 0.49322(15) 0.4351(2) 0.0709(9) Uani 1 1 d . . . . .
H15 H 0.8593 0.544868 0.435115 0.085 Uiso 1 1 calc R U . . .
C16 C 0.85069(19) 0.45685(15) 0.3651(2) 0.0590(8) Uani 1 1 d . . . . .
H16 H 0.836807 0.483292 0.316496 0.071 Uiso 1 1 calc R U . . .
C17 C 0.85720(15) 0.37918(13) 0.36362(14) 0.0398(5) Uani 1 1 d . . . . .
C18 C 0.84100(16) 0.33973(15) 0.29310(14) 0.0448(6) Uani 1 1 d . . . . .
H18 H 0.827163 0.365567 0.244123 0.054 Uiso 1 1 calc R U . . .
C19 C 0.84421(15) 0.26391(14) 0.29124(12) 0.0387(5) Uani 1 1 d . . . . .
C110 C 0.82320(18) 0.2222(2) 0.21884(14) 0.0574(8) Uani 1 1 d . . . . .
H110 H 0.807566 0.246754 0.169116 0.069 Uiso 1 1 calc R U . . .
C111 C 0.8253(2) 0.1485(2) 0.22031(17) 0.0650(9) Uani 1 1 d . . . . .
H111 H 0.810334 0.122117 0.17171 0.078 Uiso 1 1 calc R U . . .
C112 C 0.84933(19) 0.11067(17) 0.29264(16) 0.0570(7) Uani 1 1 d . . . . .
H112 H 0.851246 0.058916 0.292567 0.068 Uiso 1 1 calc R U . . .
C113 C 0.86984(17) 0.14721(13) 0.36269(14) 0.0409(5) Uani 1 1 d . . . . .
H113 H 0.885604 0.120556 0.411114 0.049 Uiso 1 1 calc R U . . .
C114 C 0.86825(14) 0.22486(12) 0.36518(12) 0.0310(4) Uani 1 1 d . . . . .
C115 C 0.91523(15) 0.22213(11) 0.51246(11) 0.0279(4) Uani 1 1 d . . . . .
O11 O 0.84105(11) 0.21246(10) 0.54768(9) 0.0447(4) Uani 1 1 d . . . . .
H11 H 0.861961 0.190472 0.590944 0.067 Uiso 1 1 calc R U . . .
O12 O 0.99775(12) 0.19791(11) 0.53746(10) 0.0586(5) Uani 1 1 d . . . . .
C21 C 0.80962(16) 0.02403(11) 0.55582(11) 0.0319(4) Uani 1 1 d . . . . .
H21 H 0.869063 0.034675 0.594605 0.038 Uiso 1 1 calc R U . . .
C22 C 0.81488(17) -0.02151(11) 0.49226(12) 0.0348(5) Uani 1 1 d . . . . .
C23 C 0.72585(19) -0.03381(12) 0.43626(12) 0.0430(6) Uani 1 1 d . . . . .
H23 H 0.725943 -0.064123 0.391625 0.052 Uiso 1 1 calc R U . . .
C24 C 0.63801(19) -0.00244(12) 0.44513(13) 0.0420(5) Uani 1 1 d . . . . .
H24 H 0.577661 -0.010528 0.406361 0.05 Uiso 1 1 calc R U . . .
C25 C 0.63732(17) 0.04081(11) 0.51032(13) 0.0374(5) Uani 1 1 d . . . . .
H25 H 0.576504 0.061826 0.517523 0.045 Uiso 1 1 calc R U . . .
N21 N 0.72338(13) 0.05277(9) 0.56323(10) 0.0320(4) Uani 1 1 d . . . . .
H21A H 0.722753 0.080772 0.604533 0.038 Uiso 1 1 calc R U . . .
N22 N 0.90509(19) -0.05016(13) 0.48625(16) 0.0529(6) Uani 1 1 d . . . . .
H22A H 0.953(3) -0.045(2) 0.528(2) 0.097(13) Uiso 1 1 d . . . . .
H22B H 0.902(2) -0.0819(17) 0.4539(18) 0.061(9) Uiso 1 1 d . . . . .
C31 C 1.09794(14) 0.18834(11) 0.29213(11) 0.0302(4) Uani 1 1 d . . . . .
C32 C 1.13013(14) 0.19069(11) 0.37381(11) 0.0284(4) Uani 1 1 d . . . . .
H32 H 1.147597 0.147529 0.404177 0.034 Uiso 1 1 calc R U . . .
C33 C 1.13593(14) 0.25817(11) 0.40960(12) 0.0315(4) Uani 1 1 d . . . . .
C34 C 1.11049(15) 0.32165(12) 0.36730(14) 0.0361(5) Uani 1 1 d . . . . .
H34 H 1.114561 0.367596 0.393211 0.043 Uiso 1 1 calc R U . . .
C35 C 1.07886(15) 0.31580(12) 0.28576(14) 0.0378(5) Uani 1 1 d . . . . .
C36 C 1.07238(15) 0.24994(12) 0.24587(13) 0.0347(5) Uani 1 1 d . . . . .
H36 H 1.051449 0.24719 0.189578 0.042 Uiso 1 1 calc R U . . .
N31 N 1.09099(14) 0.11666(10) 0.25273(10) 0.0387(4) Uani 1 1 d . . . . .
N32 N 1.17312(14) 0.26157(11) 0.49726(11) 0.0385(4) Uani 1 1 d . . . . .
N33 N 1.04908(16) 0.38263(13) 0.23957(15) 0.0535(6) Uani 1 1 d . . . . .
O31 O 1.06570(15) 0.11520(11) 0.18053(9) 0.0574(5) Uani 1 1 d . . . . .
O32 O 1.11169(15) 0.06299(9) 0.29491(10) 0.0564(5) Uani 1 1 d . . . . .
O33 O 1.21012(12) 0.20636(9) 0.53117(9) 0.0434(4) Uani 1 1 d . . . . .
O34 O 1.16588(16) 0.31989(10) 0.52916(11) 0.0613(5) Uani 1 1 d . . . . .
O35 O 1.06525(17) 0.44096(11) 0.27415(15) 0.0751(7) Uani 1 1 d . . . . .
O36 O 1.00809(14) 0.37541(12) 0.16958(14) 0.0696(6) Uani 1 1 d . . . . .
C41 C 0.84176(13) 0.18105(11) 0.80323(11) 0.0257(4) Uani 1 1 d . . . . .
C42 C 0.85616(14) 0.13674(12) 0.87124(11) 0.0289(4) Uani 1 1 d . . . . .
C43 C 0.84908(17) 0.05926(12) 0.86753(13) 0.0380(5) Uani 1 1 d . . . . .
H43 H 0.833779 0.035739 0.817187 0.046 Uiso 1 1 calc R U . . .
C44 C 0.8639(2) 0.01849(15) 0.93511(14) 0.0510(6) Uani 1 1 d . . . . .
H44 H 0.858133 -0.033059 0.931525 0.061 Uiso 1 1 calc R U . . .
C45 C 0.8879(2) 0.05244(17) 1.01062(14) 0.0559(7) Uani 1 1 d . . . . .
H45 H 0.89792 0.023375 1.05732 0.067 Uiso 1 1 calc R U . . .
C46 C 0.89672(17) 0.12549(16) 1.01728(13) 0.0458(6) Uani 1 1 d . . . . .
H46 H 0.913625 0.147003 1.06865 0.055 Uiso 1 1 calc R U . . .
C47 C 0.88111(14) 0.17112(13) 0.94846(11) 0.0333(5) Uani 1 1 d . . . . .
C48 C 0.88949(15) 0.24616(13) 0.95394(12) 0.0362(5) Uani 1 1 d . . . . .
H48 H 0.906575 0.268163 1.005061 0.043 Uiso 1 1 calc R U . . .
C49 C 0.87362(14) 0.29031(12) 0.88675(12) 0.0340(5) Uani 1 1 d . . . . .
C410 C 0.88068(18) 0.36810(13) 0.89165(15) 0.0464(6) Uani 1 1 d . . . . .
H410 H 0.896464 0.390822 0.942418 0.056 Uiso 1 1 calc R U . . .
C411 C 0.8653(2) 0.40977(14) 0.82554(17) 0.0531(7) Uani 1 1 d . . . . .
H411 H 0.871706 0.461215 0.830376 0.064 Uiso 1 1 calc R U . . .
C412 C 0.83982(19) 0.37758(13) 0.74904(16) 0.0457(6) Uani 1 1 d . . . . .
H412 H 0.828439 0.407634 0.703046 0.055 Uiso 1 1 calc R U . . .
C413 C 0.83148(16) 0.30393(12) 0.74088(13) 0.0355(5) Uani 1 1 d . . . . .
H413 H 0.813754 0.283219 0.689143 0.043 Uiso 1 1 calc R U . . .
C414 C 0.84896(14) 0.25728(11) 0.80887(11) 0.0283(4) Uani 1 1 d . . . . .
C415 C 0.81993(14) 0.14720(10) 0.72151(10) 0.0249(4) Uani 1 1 d . . . . .
O41 O 0.73417(10) 0.12073(8) 0.69590(8) 0.0339(3) Uani 1 1 d . . . . .
O42 O 0.88835(10) 0.14849(8) 0.68388(8) 0.0313(3) Uani 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 C2 1.381(3) . ?
C1 C6 1.382(3) . ?
C1 N1 1.478(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.95 . ?
C3 C4 1.380(3) . ?
C3 N2 1.471(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.95 . ?
C5 C6 1.382(3) . ?
C5 N3 1.472(3) . ?
C6 H6 0.95 . ?
N1 O1 1.215(2) . ?
N1 O2 1.223(3) . ?
N2 O4 1.214(2) . ?
N2 O3 1.227(2) . ?
N3 O5 1.222(3) . ?
N3 O6 1.223(2) . ?
C11 C114 1.405(3) . ?
C11 C12 1.405(3) . ?
C11 C115 1.489(3) . ?
C12 C13 1.424(3) . ?
C12 C17 1.439(3) . ?
C13 C14 1.357(4) . ?
C13 H13 0.95 . ?
C14 C15 1.407(5) . ?
C14 H14 0.95 . ?
C15 C16 1.356(5) . ?
C15 H15 0.95 . ?
C16 C17 1.429(4) . ?
C16 H16 0.95 . ?
C17 C18 1.390(4) . ?
C18 C19 1.393(4) . ?
C18 H18 0.95 . ?
C19 C114 1.435(3) . ?
C19 C110 1.438(3) . ?
C110 C111 1.352(5) . ?
C110 H110 0.95 . ?
C111 C112 1.401(4) . ?
C111 H111 0.95 . ?
C112 C113 1.355(3) . ?
C112 H112 0.95 . ?
C113 C114 1.426(3) . ?
C113 H113 0.95 . ?
C115 O12 1.200(3) . ?
C115 O11 1.307(2) . ?
O11 H11 0.84 . ?
C21 N21 1.324(3) . ?
C21 C22 1.393(3) . ?
C21 H21 0.95 . ?
C22 N22 1.366(3) . ?
C22 C23 1.392(3) . ?
C23 C24 1.371(4) . ?
C23 H23 0.95 . ?
C24 C25 1.378(3) . ?
C24 H24 0.95 . ?
C25 N21 1.336(3) . ?
C25 H25 0.95 . ?
N21 H21A 0.88 . ?
N22 H22A 0.86(4) . ?
N22 H22B 0.80(3) . ?
C31 C32 1.379(3) . ?
C31 C36 1.382(3) . ?
C31 N31 1.474(3) . ?
C32 C33 1.378(3) . ?
C32 H32 0.95 . ?
C33 C34 1.377(3) . ?
C33 N32 1.484(3) . ?
C34 C35 1.380(3) . ?
C34 H34 0.95 . ?
C35 C36 1.384(3) . ?
C35 N33 1.469(3) . ?
C36 H36 0.95 . ?
N31 O31 1.216(2) . ?
N31 O32 1.219(2) . ?
N32 O34 1.217(3) . ?
N32 O33 1.221(2) . ?
N33 O36 1.219(3) . ?
N33 O35 1.221(3) . ?
C41 C414 1.404(3) . ?
C41 C42 1.404(3) . ?
C41 C415 1.508(2) . ?
C42 C43 1.426(3) . ?
C42 C47 1.444(3) . ?
C43 C44 1.361(3) . ?
C43 H43 0.95 . ?
C44 C45 1.414(4) . ?
C44 H44 0.95 . ?
C45 C46 1.348(4) . ?
C45 H45 0.95 . ?
C46 C47 1.429(3) . ?
C46 H46 0.95 . ?
C47 C48 1.383(3) . ?
C48 C49 1.391(3) . ?
C48 H48 0.95 . ?
C49 C410 1.432(3) . ?
C49 C414 1.443(3) . ?
C410 C411 1.350(4) . ?
C410 H410 0.95 . ?
C411 C412 1.416(4) . ?
C411 H411 0.95 . ?
C412 C413 1.361(3) . ?
C412 H412 0.95 . ?
C413 C414 1.428(3) . ?
C413 H413 0.95 . ?
C415 O42 1.253(2) . ?
C415 O41 1.255(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 123.18(19) . . ?
C2 C1 N1 118.47(19) . . ?
C6 C1 N1 118.35(18) . . ?
C1 C2 C3 117.34(19) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 122.42(18) . . ?
C4 C3 N2 118.30(18) . . ?
C2 C3 N2 119.28(18) . . ?
C5 C4 C3 117.16(19) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 C6 123.60(19) . . ?
C4 C5 N3 117.64(19) . . ?
C6 C5 N3 118.76(18) . . ?
C1 C6 C5 116.30(18) . . ?
C1 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
O1 N1 O2 124.9(2) . . ?
O1 N1 C1 117.8(2) . . ?
O2 N1 C1 117.33(17) . . ?
O4 N2 O3 124.46(18) . . ?
O4 N2 C3 117.85(17) . . ?
O3 N2 C3 117.67(17) . . ?
O5 N3 O6 124.6(2) . . ?
O5 N3 C5 117.67(18) . . ?
O6 N3 C5 117.7(2) . . ?
C114 C11 C12 121.72(18) . . ?
C114 C11 C115 117.69(18) . . ?
C12 C11 C115 120.59(17) . . ?
C11 C12 C13 122.88(19) . . ?
C11 C12 C17 118.7(2) . . ?
C13 C12 C17 118.5(2) . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 122.5(2) . . ?
C18 C17 C12 119.0(2) . . ?
C16 C17 C12 118.5(2) . . ?
C17 C18 C19 122.74(19) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C18 C19 C114 118.7(2) . . ?
C18 C19 C110 123.4(2) . . ?
C114 C19 C110 117.8(2) . . ?
C111 C110 C19 121.1(2) . . ?
C111 C110 H110 119.4 . . ?
C19 C110 H110 119.4 . . ?
C110 C111 C112 120.8(2) . . ?
C110 C111 H111 119.6 . . ?
C112 C111 H111 119.6 . . ?
C113 C112 C111 120.6(3) . . ?
C113 C112 H112 119.7 . . ?
C111 C112 H112 119.7 . . ?
C112 C113 C114 121.3(2) . . ?
C112 C113 H113 119.3 . . ?
C114 C113 H113 119.3 . . ?
C11 C114 C113 122.59(19) . . ?
C11 C114 C19 119.1(2) . . ?
C113 C114 C19 118.3(2) . . ?
O12 C115 O11 123.28(18) . . ?
O12 C115 C11 123.17(17) . . ?
O11 C115 C11 113.52(16) . . ?
C115 O11 H11 109.5 . . ?
N21 C21 C22 121.30(19) . . ?
N21 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
N22 C22 C23 123.3(2) . . ?
N22 C22 C21 119.8(2) . . ?
C23 C22 C21 116.8(2) . . ?
C24 C23 C22 120.4(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.0(2) . . ?
C23 C24 H24 120 . . ?
C25 C24 H24 120 . . ?
N21 C25 C24 119.1(2) . . ?
N21 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C21 N21 C25 122.41(18) . . ?
C21 N21 H21A 118.8 . . ?
C25 N21 H21A 118.8 . . ?
C22 N22 H22A 115(3) . . ?
C22 N22 H22B 115(2) . . ?
H22A N22 H22B 125(3) . . ?
C32 C31 C36 123.0(2) . . ?
C32 C31 N31 118.15(18) . . ?
C36 C31 N31 118.80(18) . . ?
C33 C32 C31 117.31(19) . . ?
C33 C32 H32 121.3 . . ?
C31 C32 H32 121.3 . . ?
C34 C33 C32 122.72(19) . . ?
C34 C33 N32 119.49(19) . . ?
C32 C33 N32 117.79(18) . . ?
C33 C34 C35 117.3(2) . . ?
C33 C34 H34 121.4 . . ?
C35 C34 H34 121.4 . . ?
C34 C35 C36 123.0(2) . . ?
C34 C35 N33 118.2(2) . . ?
C36 C35 N33 118.7(2) . . ?
C31 C36 C35 116.6(2) . . ?
C31 C36 H36 121.7 . . ?
C35 C36 H36 121.7 . . ?
O31 N31 O32 124.6(2) . . ?
O31 N31 C31 117.79(18) . . ?
O32 N31 C31 117.60(17) . . ?
O34 N32 O33 125.4(2) . . ?
O34 N32 C33 117.0(2) . . ?
O33 N32 C33 117.60(17) . . ?
O36 N33 O35 124.9(2) . . ?
O36 N33 C35 117.1(2) . . ?
O35 N33 C35 118.0(2) . . ?
C414 C41 C42 121.64(17) . . ?
C414 C41 C415 118.11(17) . . ?
C42 C41 C415 120.24(17) . . ?
C41 C42 C43 123.00(18) . . ?
C41 C42 C47 118.51(19) . . ?
C43 C42 C47 118.48(18) . . ?
C44 C43 C42 120.9(2) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C45 120.4(2) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C46 C45 C44 120.9(2) . . ?
C46 C45 H45 119.5 . . ?
C44 C45 H45 119.5 . . ?
C45 C46 C47 121.2(2) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 H46 119.4 . . ?
C48 C47 C46 122.1(2) . . ?
C48 C47 C42 119.79(19) . . ?
C46 C47 C42 118.1(2) . . ?
C47 C48 C49 121.86(18) . . ?
C47 C48 H48 119.1 . . ?
C49 C48 H48 119.1 . . ?
C48 C49 C410 122.4(2) . . ?
C48 C49 C414 119.4(2) . . ?
C410 C49 C414 118.2(2) . . ?
C411 C410 C49 121.3(2) . . ?
C411 C410 H410 119.4 . . ?
C49 C410 H410 119.4 . . ?
C410 C411 C412 120.7(2) . . ?
C410 C411 H411 119.7 . . ?
C412 C411 H411 119.7 . . ?
C413 C412 C411 120.5(2) . . ?
C413 C412 H412 119.7 . . ?
C411 C412 H412 119.7 . . ?
C412 C413 C414 121.0(2) . . ?
C412 C413 H413 119.5 . . ?
C414 C413 H413 119.5 . . ?
C41 C414 C413 122.96(18) . . ?
C41 C414 C49 118.74(18) . . ?
C413 C414 C49 118.29(19) . . ?
O42 C415 O41 124.95(17) . . ?
O42 C415 C41 117.54(16) . . ?
O41 C415 C41 117.50(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 0.4(3) . . . . ?
N1 C1 C2 C3 -179.68(16) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C2 C3 N2 178.92(16) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
N2 C3 C4 C5 -179.38(16) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 N3 -178.44(17) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C5 -179.82(17) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
N3 C5 C6 C1 178.38(17) . . . . ?
C2 C1 N1 O1 173.44(18) . . . . ?
C6 C1 N1 O1 -6.6(3) . . . . ?
C2 C1 N1 O2 -7.1(3) . . . . ?
C6 C1 N1 O2 172.84(19) . . . . ?
C4 C3 N2 O4 -13.3(3) . . . . ?
C2 C3 N2 O4 167.37(18) . . . . ?
C4 C3 N2 O3 165.28(17) . . . . ?
C2 C3 N2 O3 -14.1(3) . . . . ?
C4 C5 N3 O5 -18.1(3) . . . . ?
C6 C5 N3 O5 162.8(2) . . . . ?
C4 C5 N3 O6 160.01(19) . . . . ?
C6 C5 N3 O6 -19.1(3) . . . . ?
C114 C11 C12 C13 177.20(18) . . . . ?
C115 C11 C12 C13 -3.4(3) . . . . ?
C114 C11 C12 C17 -2.8(3) . . . . ?
C115 C11 C12 C17 176.60(17) . . . . ?
C11 C12 C13 C14 -179.5(2) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -1.1(4) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 178.1(2) . . . . ?
C15 C16 C17 C12 -0.8(4) . . . . ?
C11 C12 C17 C18 1.5(3) . . . . ?
C13 C12 C17 C18 -178.48(19) . . . . ?
C11 C12 C17 C16 -179.60(19) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C16 C17 C18 C19 -178.0(2) . . . . ?
C12 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C114 -2.0(3) . . . . ?
C17 C18 C19 C110 177.1(2) . . . . ?
C18 C19 C110 C111 -178.6(2) . . . . ?
C114 C19 C110 C111 0.5(3) . . . . ?
C19 C110 C111 C112 -0.8(4) . . . . ?
C110 C111 C112 C113 0.7(4) . . . . ?
C111 C112 C113 C114 -0.3(4) . . . . ?
C12 C11 C114 C113 -176.60(18) . . . . ?
C115 C11 C114 C113 4.0(3) . . . . ?
C12 C11 C114 C19 1.7(3) . . . . ?
C115 C11 C114 C19 -177.72(17) . . . . ?
C112 C113 C114 C11 178.3(2) . . . . ?
C112 C113 C114 C19 0.0(3) . . . . ?
C18 C19 C114 C11 0.7(3) . . . . ?
C110 C19 C114 C11 -178.44(18) . . . . ?
C18 C19 C114 C113 179.06(19) . . . . ?
C110 C19 C114 C113 -0.1(3) . . . . ?
C114 C11 C115 O12 77.6(3) . . . . ?
C12 C11 C115 O12 -101.9(3) . . . . ?
C114 C11 C115 O11 -100.6(2) . . . . ?
C12 C11 C115 O11 79.9(2) . . . . ?
N21 C21 C22 N22 179.9(2) . . . . ?
N21 C21 C22 C23 1.5(3) . . . . ?
N22 C22 C23 C24 -178.9(2) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 N21 1.4(3) . . . . ?
C22 C21 N21 C25 -0.9(3) . . . . ?
C24 C25 N21 C21 -0.6(3) . . . . ?
C36 C31 C32 C33 0.4(3) . . . . ?
N31 C31 C32 C33 -179.86(17) . . . . ?
C31 C32 C33 C34 0.5(3) . . . . ?
C31 C32 C33 N32 -178.37(17) . . . . ?
C32 C33 C34 C35 -0.5(3) . . . . ?
N32 C33 C34 C35 178.32(17) . . . . ?
C33 C34 C35 C36 -0.3(3) . . . . ?
C33 C34 C35 N33 178.60(17) . . . . ?
C32 C31 C36 C35 -1.1(3) . . . . ?
N31 C31 C36 C35 179.14(17) . . . . ?
C34 C35 C36 C31 1.0(3) . . . . ?
N33 C35 C36 C31 -177.85(18) . . . . ?
C32 C31 N31 O31 -177.66(19) . . . . ?
C36 C31 N31 O31 2.1(3) . . . . ?
C32 C31 N31 O32 1.9(3) . . . . ?
C36 C31 N31 O32 -178.3(2) . . . . ?
C34 C33 N32 O34 10.2(3) . . . . ?
C32 C33 N32 O34 -170.92(19) . . . . ?
C34 C33 N32 O33 -168.38(18) . . . . ?
C32 C33 N32 O33 10.5(3) . . . . ?
C34 C35 N33 O36 -169.81(19) . . . . ?
C36 C35 N33 O36 9.1(3) . . . . ?
C34 C35 N33 O35 8.8(3) . . . . ?
C36 C35 N33 O35 -172.3(2) . . . . ?
C414 C41 C42 C43 179.81(18) . . . . ?
C415 C41 C42 C43 -1.4(3) . . . . ?
C414 C41 C42 C47 -1.4(3) . . . . ?
C415 C41 C42 C47 177.41(16) . . . . ?
C41 C42 C43 C44 179.8(2) . . . . ?
C47 C42 C43 C44 1.0(3) . . . . ?
C42 C43 C44 C45 -0.7(4) . . . . ?
C43 C44 C45 C46 -0.1(4) . . . . ?
C44 C45 C46 C47 0.7(4) . . . . ?
C45 C46 C47 C48 179.8(2) . . . . ?
C45 C46 C47 C42 -0.4(3) . . . . ?
C41 C42 C47 C48 0.5(3) . . . . ?
C43 C42 C47 C48 179.37(18) . . . . ?
C41 C42 C47 C46 -179.31(18) . . . . ?
C43 C42 C47 C46 -0.4(3) . . . . ?
C46 C47 C48 C49 -179.61(19) . . . . ?
C42 C47 C48 C49 0.6(3) . . . . ?
C47 C48 C49 C410 179.09(19) . . . . ?
C47 C48 C49 C414 -0.8(3) . . . . ?
C48 C49 C410 C411 179.7(2) . . . . ?
C414 C49 C410 C411 -0.4(3) . . . . ?
C49 C410 C411 C412 1.2(4) . . . . ?
C410 C411 C412 C413 -0.8(4) . . . . ?
C411 C412 C413 C414 -0.5(3) . . . . ?
C42 C41 C414 C413 -177.88(18) . . . . ?
C415 C41 C414 C413 3.3(3) . . . . ?
C42 C41 C414 C49 1.2(3) . . . . ?
C415 C41 C414 C49 -177.64(16) . . . . ?
C412 C413 C414 C41 -179.6(2) . . . . ?
C412 C413 C414 C49 1.3(3) . . . . ?
C48 C49 C414 C41 -0.1(3) . . . . ?
C410 C49 C414 C41 -179.97(18) . . . . ?
C48 C49 C414 C413 179.03(18) . . . . ?
C410 C49 C414 C413 -0.9(3) . . . . ?
C414 C41 C415 O42 71.4(2) . . . . ?
C42 C41 C415 O42 -107.4(2) . . . . ?
C414 C41 C415 O41 -107.7(2) . . . . ?
C42 C41 C415 O41 73.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O11 H11 O42 0.84 1.74 2.5755(19) 172 . yes
N21 H21A O41 0.88 1.71 2.581(2) 168 . yes
N22 H22B O12 0.80(3) 2.52(3) 3.087(3) 129(3) 3_756 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_11
_audit_block_doi                 10.5517/ccdc.csd.cc1j2tfv
_database_code_depnum_ccdc_archive 'CCDC 1402887'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T09:16:58-00:00
_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 H10 O2, C6 H3 N3 O6, C10 H8 N2'
_chemical_formula_sum            'C31 H21 N5 O8'
_chemical_formula_weight         591.53

#----------------------------------------------------------------------------#
#                   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                   7.037(3)
_cell_length_b                   9.676(4)
_cell_length_c                   19.738(8)
_cell_angle_alpha                87.593(11)
_cell_angle_beta                 82.035(11)
_cell_angle_gamma                84.659(13)
_cell_volume                     1324.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5179
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.89
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          1.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.8767
_exptl_absorpt_correction_T_max  0.9934
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.993

#----------------------------------------------------------------------------#
#                   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  0.0771
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_number            14591
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.978
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.911
_reflns_Friedel_coverage         0
_reflns_number_total             4502
_reflns_number_gt                2799
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.1661P)²+2.7168P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4502
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1522
_refine_ls_R_factor_gt           0.1019
_refine_ls_wR_factor_ref         0.3186
_refine_ls_wR_factor_gt          0.2847
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.101

#----------------------------------------------------------------------------#
#                   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 0.6903(8) 0.6173(6) 0.3161(3) 0.0321(13) Uani 1 1 d . . . . .
C2 C 0.6080(8) 0.6635(6) 0.3790(3) 0.0334(13) Uani 1 1 d . . . . .
H2 H 0.602285 0.604079 0.418619 0.04 Uiso 1 1 calc R U . . .
C3 C 0.5332(8) 0.8014(6) 0.3820(2) 0.0317(13) Uani 1 1 d . . . . .
C4 C 0.5441(8) 0.8898(6) 0.3256(3) 0.0331(13) Uani 1 1 d . . . . .
H4 H 0.4908 0.983569 0.328441 0.04 Uiso 1 1 calc R U . . .
C5 C 0.6360(8) 0.8364(6) 0.2645(2) 0.0311(13) Uani 1 1 d . . . . .
C6 C 0.7089(8) 0.6994(6) 0.2578(3) 0.0322(13) Uani 1 1 d . . . . .
H6 H 0.768747 0.664203 0.215113 0.039 Uiso 1 1 calc R U . . .
N1 N 0.7685(7) 0.4702(5) 0.3107(3) 0.0454(13) Uani 1 1 d . . . . .
N2 N 0.4376(8) 0.8558(6) 0.4473(2) 0.0446(13) Uani 1 1 d . . . . .
N3 N 0.6554(8) 0.9308(5) 0.2043(2) 0.0395(12) Uani 1 1 d . . . . .
O1 O 0.8123(7) 0.4238(5) 0.2534(3) 0.0597(13) Uani 1 1 d . . . . .
O2 O 0.7797(8) 0.4043(5) 0.3642(3) 0.0630(14) Uani 1 1 d . . . . .
O3 O 0.4313(7) 0.7765(6) 0.4974(2) 0.0606(14) Uani 1 1 d . . . . .
O4 O 0.3724(7) 0.9773(5) 0.4485(2) 0.0532(13) Uani 1 1 d . . . . .
O5 O 0.5712(8) 1.0464(5) 0.2095(2) 0.0575(14) Uani 1 1 d . . . . .
O6 O 0.7596(7) 0.8896(5) 0.15309(19) 0.0512(12) Uani 1 1 d . . . . .
C11 C 0.1717(7) 0.7076(5) 0.2709(2) 0.0272(12) Uani 1 1 d . . . . .
C12 C 0.2060(7) 0.5843(6) 0.3088(2) 0.0288(12) Uani 1 1 d . . . . .
C13 C 0.2902(8) 0.4583(6) 0.2772(3) 0.0362(14) Uani 1 1 d . . . . .
H13 H 0.318403 0.455634 0.228762 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3302(9) 0.3427(6) 0.3160(3) 0.0467(16) Uani 1 1 d . . . . .
H14 H 0.386687 0.260135 0.294339 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2892(9) 0.3433(7) 0.3877(3) 0.0495(17) Uani 1 1 d . . . . .
H15 H 0.317482 0.261064 0.413797 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2101(9) 0.4597(6) 0.4201(3) 0.0410(14) Uani 1 1 d . . . . .
H16 H 0.186936 0.459061 0.468686 0.049 Uiso 1 1 calc R U . . .
C17 C 0.1606(7) 0.5843(6) 0.3818(3) 0.0313(12) Uani 1 1 d . . . . .
C18 C 0.0754(7) 0.7042(6) 0.4134(3) 0.0321(13) Uani 1 1 d . . . . .
H18 H 0.042776 0.702666 0.461756 0.039 Uiso 1 1 calc R U . . .
C19 C 0.0362(8) 0.8268(6) 0.3763(2) 0.0307(12) Uani 1 1 d . . . . .
C110 C -0.0518(9) 0.9505(7) 0.4084(3) 0.0406(15) Uani 1 1 d . . . . .
H110 H -0.088344 0.948965 0.456589 0.049 Uiso 1 1 calc R U . . .
C111 C -0.0843(9) 1.0691(7) 0.3723(3) 0.0434(15) Uani 1 1 d . . . . .
H111 H -0.146462 1.149408 0.394651 0.052 Uiso 1 1 calc R U . . .
C112 C -0.0260(9) 1.0739(6) 0.3014(3) 0.0452(16) Uani 1 1 d . . . . .
H112 H -0.04725 1.158594 0.276302 0.054 Uiso 1 1 calc R U . . .
C113 C 0.0609(9) 0.9591(6) 0.2674(3) 0.0382(14) Uani 1 1 d . . . . .
H113 H 0.099118 0.965295 0.219409 0.046 Uiso 1 1 calc R U . . .
C114 C 0.0943(7) 0.8309(5) 0.3034(2) 0.0287(12) Uani 1 1 d . . . . .
C115 C 0.2221(8) 0.7079(5) 0.1943(2) 0.0289(12) Uani 1 1 d . . . . .
O11 O 0.3554(6) 0.7708(5) 0.16465(19) 0.0474(11) Uani 1 1 d . . . . .
O12 O 0.1149(6) 0.6347(4) 0.16555(17) 0.0383(10) Uani 1 1 d . . . . .
H12 H 0.160574 0.625018 0.124224 0.057 Uiso 1 1 calc R U . . .
C21 C 0.2630(8) 0.3716(6) 0.0254(3) 0.0334(13) Uani 1 1 d . . . . .
C22 C 0.3099(9) 0.1279(6) 0.0163(3) 0.0464(16) Uani 1 1 d . . . . .
H22 H 0.336276 0.047625 -0.010736 0.056 Uiso 1 1 calc R U . . .
C23 C 0.2801(9) 0.1142(6) 0.0860(3) 0.0462(16) Uani 1 1 d . . . . .
H23 H 0.284392 0.025365 0.108422 0.055 Uiso 1 1 calc R U . . .
C24 C 0.2440(11) 0.2327(7) 0.1223(3) 0.0554(19) Uani 1 1 d . . . . .
H24 H 0.224331 0.22411 0.170881 0.067 Uiso 1 1 calc R U . . .
C25 C 0.3018(8) 0.2572(6) -0.0148(3) 0.0359(14) Uani 1 1 d . . . . .
H25 H 0.322636 0.267603 -0.06323 0.043 Uiso 1 1 calc R U . . .
C26 C 0.2521(8) 0.5134(6) -0.0065(2) 0.0332(13) Uani 1 1 d . . . . .
C27 C 0.2907(11) 0.5369(7) -0.0760(3) 0.0534(18) Uani 1 1 d . . . . .
H27 H 0.329959 0.460858 -0.105158 0.064 Uiso 1 1 calc R U . . .
C28 C 0.2729(12) 0.6690(7) -0.1035(3) 0.061(2) Uani 1 1 d . . . . .
H28 H 0.295403 0.684593 -0.151642 0.074 Uiso 1 1 calc R U . . .
C29 C 0.2219(9) 0.7796(7) -0.0604(3) 0.0446(15) Uani 1 1 d . . . . .
H29 H 0.209348 0.872529 -0.0778 0.054 Uiso 1 1 calc R U . . .
C210 C 0.1904(9) 0.7492(6) 0.0086(3) 0.0381(14) Uani 1 1 d . . . . .
H210 H 0.157511 0.823961 0.038956 0.046 Uiso 1 1 calc R U . . .
N21 N 0.2345(9) 0.3608(5) 0.0935(2) 0.0558(16) Uani 1 1 d . . . . .
N22 N 0.2035(7) 0.6198(5) 0.0352(2) 0.0326(11) Uani 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 1.369(8) . ?
C1 C2 1.370(7) . ?
C1 N1 1.480(7) . ?
C2 C3 1.389(8) . ?
C2 H2 0.95 . ?
C3 C4 1.372(8) . ?
C3 N2 1.464(7) . ?
C4 C5 1.383(7) . ?
C4 H4 0.95 . ?
C5 C6 1.381(7) . ?
C5 N3 1.466(7) . ?
C6 H6 0.95 . ?
N1 O2 1.219(7) . ?
N1 O1 1.224(7) . ?
N2 O4 1.221(7) . ?
N2 O3 1.225(7) . ?
N3 O5 1.218(6) . ?
N3 O6 1.222(6) . ?
C11 C12 1.401(7) . ?
C11 C114 1.407(7) . ?
C11 C115 1.503(7) . ?
C12 C13 1.433(7) . ?
C12 C17 1.431(7) . ?
C13 C14 1.359(8) . ?
C13 H13 0.95 . ?
C14 C15 1.404(9) . ?
C14 H14 0.95 . ?
C15 C16 1.354(9) . ?
C15 H15 0.95 . ?
C16 C17 1.437(8) . ?
C16 H16 0.95 . ?
C17 C18 1.386(8) . ?
C18 C19 1.394(8) . ?
C18 H18 0.95 . ?
C19 C110 1.425(7) . ?
C19 C114 1.441(7) . ?
C110 C111 1.344(9) . ?
C110 H110 0.95 . ?
C111 C112 1.403(8) . ?
C111 H111 0.95 . ?
C112 C113 1.371(8) . ?
C112 H112 0.95 . ?
C113 C114 1.419(8) . ?
C113 H113 0.95 . ?
C115 O11 1.232(7) . ?
C115 O12 1.283(7) . ?
O12 H12 0.84 . ?
C21 N21 1.333(7) . ?
C21 C25 1.372(7) . ?
C21 C26 1.486(8) . ?
C22 C23 1.367(8) . ?
C22 C25 1.370(8) . ?
C22 H22 0.95 . ?
C23 C24 1.362(9) . ?
C23 H23 0.95 . ?
C24 N21 1.342(8) . ?
C24 H24 0.95 . ?
C25 H25 0.95 . ?
C26 N22 1.335(7) . ?
C26 C27 1.374(8) . ?
C27 C28 1.369(9) . ?
C27 H27 0.95 . ?
C28 C29 1.385(9) . ?
C28 H28 0.95 . ?
C29 C210 1.372(8) . ?
C29 H29 0.95 . ?
C210 N22 1.338(7) . ?
C210 H210 0.95 . ?

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 124.1(5) . . ?
C6 C1 N1 117.6(5) . . ?
C2 C1 N1 118.3(5) . . ?
C1 C2 C3 116.8(5) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 122.5(5) . . ?
C4 C3 N2 118.1(5) . . ?
C2 C3 N2 119.4(5) . . ?
C3 C4 C5 117.2(5) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 123.1(5) . . ?
C6 C5 N3 119.0(4) . . ?
C4 C5 N3 117.9(5) . . ?
C1 C6 C5 116.3(5) . . ?
C1 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
O2 N1 O1 125.4(5) . . ?
O2 N1 C1 116.9(5) . . ?
O1 N1 C1 117.7(5) . . ?
O4 N2 O3 124.5(5) . . ?
O4 N2 C3 118.0(5) . . ?
O3 N2 C3 117.5(5) . . ?
O5 N3 O6 124.4(5) . . ?
O5 N3 C5 117.7(5) . . ?
O6 N3 C5 117.8(5) . . ?
C12 C11 C114 121.0(4) . . ?
C12 C11 C115 119.2(4) . . ?
C114 C11 C115 119.8(5) . . ?
C11 C12 C13 122.2(5) . . ?
C11 C12 C17 119.2(5) . . ?
C13 C12 C17 118.6(5) . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 121.1(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.8(6) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.7(5) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C12 119.6(5) . . ?
C18 C17 C16 122.0(5) . . ?
C12 C17 C16 118.4(5) . . ?
C17 C18 C19 121.9(5) . . ?
C17 C18 H18 119 . . ?
C19 C18 H18 119 . . ?
C18 C19 C110 122.3(5) . . ?
C18 C19 C114 119.0(5) . . ?
C110 C19 C114 118.7(5) . . ?
C111 C110 C19 121.7(5) . . ?
C111 C110 H110 119.1 . . ?
C19 C110 H110 119.1 . . ?
C110 C111 C112 119.8(5) . . ?
C110 C111 H111 120.1 . . ?
C112 C111 H111 120.1 . . ?
C113 C112 C111 121.5(6) . . ?
C113 C112 H112 119.3 . . ?
C111 C112 H112 119.3 . . ?
C112 C113 C114 120.6(5) . . ?
C112 C113 H113 119.7 . . ?
C114 C113 H113 119.7 . . ?
C11 C114 C113 123.2(4) . . ?
C11 C114 C19 119.0(5) . . ?
C113 C114 C19 117.7(5) . . ?
O11 C115 O12 125.6(5) . . ?
O11 C115 C11 121.8(5) . . ?
O12 C115 C11 112.6(5) . . ?
C115 O12 H12 109.5 . . ?
N21 C21 C25 122.1(5) . . ?
N21 C21 C26 117.5(5) . . ?
C25 C21 C26 120.3(5) . . ?
C23 C22 C25 120.1(5) . . ?
C23 C22 H22 120 . . ?
C25 C22 H22 120 . . ?
C24 C23 C22 117.6(6) . . ?
C24 C23 H23 121.2 . . ?
C22 C23 H23 121.2 . . ?
N21 C24 C23 123.8(6) . . ?
N21 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
C22 C25 C21 118.9(5) . . ?
C22 C25 H25 120.6 . . ?
C21 C25 H25 120.6 . . ?
N22 C26 C27 120.4(5) . . ?
N22 C26 C21 117.3(4) . . ?
C27 C26 C21 122.3(5) . . ?
C28 C27 C26 120.5(6) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.4(6) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C210 C29 C28 117.2(6) . . ?
C210 C29 H29 121.4 . . ?
C28 C29 H29 121.4 . . ?
N22 C210 C29 123.4(5) . . ?
N22 C210 H210 118.3 . . ?
C29 C210 H210 118.3 . . ?
C21 N21 C24 117.6(5) . . ?
C26 N22 C210 119.2(4) . . ?

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 2.6(8) . . . . ?
N1 C1 C2 C3 -179.0(5) . . . . ?
C1 C2 C3 C4 -1.6(9) . . . . ?
C1 C2 C3 N2 178.0(5) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
N2 C3 C4 C5 179.7(5) . . . . ?
C3 C4 C5 C6 2.5(9) . . . . ?
C3 C4 C5 N3 -177.7(5) . . . . ?
C2 C1 C6 C5 -1.0(8) . . . . ?
N1 C1 C6 C5 -179.5(5) . . . . ?
C4 C5 C6 C1 -1.6(9) . . . . ?
N3 C5 C6 C1 178.6(5) . . . . ?
C6 C1 N1 O2 168.3(5) . . . . ?
C2 C1 N1 O2 -10.2(8) . . . . ?
C6 C1 N1 O1 -13.3(8) . . . . ?
C2 C1 N1 O1 168.1(5) . . . . ?
C4 C3 N2 O4 -0.1(8) . . . . ?
C2 C3 N2 O4 -179.7(6) . . . . ?
C4 C3 N2 O3 -179.0(5) . . . . ?
C2 C3 N2 O3 1.5(8) . . . . ?
C6 C5 N3 O5 171.8(6) . . . . ?
C4 C5 N3 O5 -8.0(8) . . . . ?
C6 C5 N3 O6 -10.4(8) . . . . ?
C4 C5 N3 O6 169.8(5) . . . . ?
C114 C11 C12 C13 -178.0(5) . . . . ?
C115 C11 C12 C13 0.9(8) . . . . ?
C114 C11 C12 C17 0.3(8) . . . . ?
C115 C11 C12 C17 179.1(5) . . . . ?
C11 C12 C13 C14 176.7(5) . . . . ?
C17 C12 C13 C14 -1.6(8) . . . . ?
C12 C13 C14 C15 0.3(10) . . . . ?
C13 C14 C15 C16 -0.5(10) . . . . ?
C14 C15 C16 C17 1.9(10) . . . . ?
C11 C12 C17 C18 3.0(8) . . . . ?
C13 C12 C17 C18 -178.7(5) . . . . ?
C11 C12 C17 C16 -175.4(5) . . . . ?
C13 C12 C17 C16 2.9(8) . . . . ?
C15 C16 C17 C18 178.5(6) . . . . ?
C15 C16 C17 C12 -3.1(9) . . . . ?
C12 C17 C18 C19 -1.6(8) . . . . ?
C16 C17 C18 C19 176.8(5) . . . . ?
C17 C18 C19 C110 179.9(6) . . . . ?
C17 C18 C19 C114 -3.0(8) . . . . ?
C18 C19 C110 C111 178.3(6) . . . . ?
C114 C19 C110 C111 1.1(9) . . . . ?
C19 C110 C111 C112 -1.8(10) . . . . ?
C110 C111 C112 C113 1.2(10) . . . . ?
C111 C112 C113 C114 0.1(10) . . . . ?
C12 C11 C114 C113 178.6(5) . . . . ?
C115 C11 C114 C113 -0.3(8) . . . . ?
C12 C11 C114 C19 -4.8(8) . . . . ?
C115 C11 C114 C19 176.3(5) . . . . ?
C112 C113 C114 C11 175.9(6) . . . . ?
C112 C113 C114 C19 -0.8(9) . . . . ?
C18 C19 C114 C11 6.2(8) . . . . ?
C110 C19 C114 C11 -176.6(5) . . . . ?
C18 C19 C114 C113 -177.0(5) . . . . ?
C110 C19 C114 C113 0.2(8) . . . . ?
C12 C11 C115 O11 -111.0(6) . . . . ?
C114 C11 C115 O11 67.9(7) . . . . ?
C12 C11 C115 O12 67.7(6) . . . . ?
C114 C11 C115 O12 -113.4(6) . . . . ?
C25 C22 C23 C24 -0.4(10) . . . . ?
C22 C23 C24 N21 0.6(12) . . . . ?
C23 C22 C25 C21 -0.1(10) . . . . ?
N21 C21 C25 C22 0.5(9) . . . . ?
C26 C21 C25 C22 -179.7(6) . . . . ?
N21 C21 C26 N22 -3.8(8) . . . . ?
C25 C21 C26 N22 176.4(6) . . . . ?
N21 C21 C26 C27 175.9(6) . . . . ?
C25 C21 C26 C27 -3.9(9) . . . . ?
N22 C26 C27 C28 -2.4(11) . . . . ?
C21 C26 C27 C28 177.9(7) . . . . ?
C26 C27 C28 C29 2.2(12) . . . . ?
C27 C28 C29 C210 -0.5(11) . . . . ?
C28 C29 C210 N22 -1.1(10) . . . . ?
C25 C21 N21 C24 -0.3(10) . . . . ?
C26 C21 N21 C24 179.9(6) . . . . ?
C23 C24 N21 C21 -0.3(12) . . . . ?
C27 C26 N22 C210 0.8(9) . . . . ?
C21 C26 N22 C210 -179.4(5) . . . . ?
C29 C210 N22 C26 0.9(9) . . . . ?

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
O12 H12 N22 0.84 1.74 2.568(5) 167 . 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_10
_audit_block_doi                 10.5517/ccdc.csd.cc1j2tdt
_database_code_depnum_ccdc_archive 'CCDC 1402886'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T09:02:04-00:00
_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 H10 O2, C6 H3 N3 O6, C5 H5 N3 O2'
_chemical_formula_sum            'C26 H18 N6 O10'
_chemical_formula_weight         574.46

#----------------------------------------------------------------------------#
#                   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                   8.8909(11)
_cell_length_b                   7.8185(10)
_cell_length_c                   36.688(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.018(4)
_cell_angle_gamma                90
_cell_volume                     2536.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9674
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      28.26
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.97
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.8935
_exptl_absorpt_correction_T_max  0.9824
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.982

#----------------------------------------------------------------------------#
#                   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  0.0297
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_number            44818
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.834
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             4716
_reflns_number_gt                4214
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0902P)²+3.7966P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4716
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.081
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.1959
_refine_ls_wR_factor_gt          0.1902
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   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 0.8716(4) 0.4956(4) 0.32905(8) 0.0430(7) Uani 1 1 d . . . . .
C2 C 0.9665(3) 0.4335(4) 0.35801(8) 0.0427(7) Uani 1 1 d . . . . .
H2 H 1.070955 0.414228 0.356165 0.051 Uiso 1 1 calc R U . . .
C3 C 0.9020(4) 0.4008(4) 0.38997(9) 0.0457(7) Uani 1 1 d . . . . .
C4 C 0.7523(4) 0.4240(4) 0.39367(10) 0.0470(8) Uani 1 1 d . . . . .
H4 H 0.710756 0.397849 0.415834 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6643(3) 0.4877(4) 0.36341(10) 0.0500(8) Uani 1 1 d . . . . .
C6 C 0.7205(4) 0.5254(4) 0.33095(9) 0.0493(8) Uani 1 1 d . . . . .
H6 H 0.657576 0.570162 0.310659 0.059 Uiso 1 1 calc R U . . .
N1 N 0.9371(4) 0.5307(4) 0.29433(8) 0.0627(8) Uani 1 1 d . . . . .
N2 N 1.0007(4) 0.3443(5) 0.42233(9) 0.0764(11) Uani 1 1 d . . . . .
N3 N 0.5025(4) 0.5168(4) 0.36605(14) 0.0772(12) Uani 1 1 d . . . . .
O1 O 0.8599(4) 0.6078(6) 0.27074(8) 0.0980(12) Uani 1 1 d . . . . .
O2 O 1.0681(4) 0.4884(6) 0.29238(8) 0.0997(12) Uani 1 1 d . . . . .
O3 O 1.1319(4) 0.3942(8) 0.42528(12) 0.156(2) Uani 1 1 d . . . . .
O4 O 0.9469(4) 0.2552(4) 0.44457(8) 0.0850(10) Uani 1 1 d . . . . .
O5 O 0.4529(3) 0.4804(3) 0.39489(13) 0.0973(13) Uani 1 1 d . . . . .
O6 O 0.4278(3) 0.5774(6) 0.33897(12) 0.1150(16) Uani 1 1 d . . . . .
C11 C 0.6942(3) 0.0047(3) 0.35396(7) 0.0285(5) Uani 1 1 d . . . . .
C12 C 0.8460(3) -0.0475(3) 0.35610(7) 0.0318(6) Uani 1 1 d . . . . .
C13 C 0.9217(3) -0.1303(4) 0.38755(8) 0.0424(7) Uani 1 1 d . . . . .
H13 H 0.86797 -0.153346 0.408067 0.051 Uiso 1 1 calc R U . . .
C14 C 1.0689(4) -0.1766(5) 0.38859(11) 0.0591(9) Uani 1 1 d . . . . .
H14 H 1.116862 -0.231494 0.40981 0.071 Uiso 1 1 calc R U . . .
C15 C 1.1517(4) -0.1445(5) 0.35876(13) 0.0666(11) Uani 1 1 d . . . . .
H15 H 1.254737 -0.178272 0.359895 0.08 Uiso 1 1 calc R U . . .
C16 C 1.0858(4) -0.0660(5) 0.32855(12) 0.0599(9) Uani 1 1 d . . . . .
H16 H 1.143148 -0.045097 0.308568 0.072 Uiso 1 1 calc R U . . .
C17 C 0.9311(3) -0.0134(4) 0.32596(8) 0.0399(7) Uani 1 1 d . . . . .
C18 C 0.8612(4) 0.0687(4) 0.29509(8) 0.0445(7) Uani 1 1 d . . . . .
H18 H 0.918147 0.090254 0.275067 0.053 Uiso 1 1 calc R U . . .
C19 C 0.7119(3) 0.1200(4) 0.29255(7) 0.0389(6) Uani 1 1 d . . . . .
C110 C 0.6421(5) 0.2062(4) 0.26111(9) 0.0545(8) Uani 1 1 d . . . . .
H110 H 0.698814 0.226941 0.241009 0.065 Uiso 1 1 calc R U . . .
C111 C 0.4984(5) 0.2586(5) 0.25918(9) 0.0618(10) Uani 1 1 d . . . . .
H111 H 0.454876 0.317737 0.238022 0.074 Uiso 1 1 calc R U . . .
C112 C 0.4106(4) 0.2265(4) 0.28851(10) 0.0559(9) Uani 1 1 d . . . . .
H112 H 0.308279 0.263432 0.286732 0.067 Uiso 1 1 calc R U . . .
C113 C 0.4710(3) 0.1434(4) 0.31918(8) 0.0422(7) Uani 1 1 d . . . . .
H113 H 0.410044 0.121952 0.338462 0.051 Uiso 1 1 calc R U . . .
C114 C 0.6243(3) 0.0884(3) 0.32275(7) 0.0312(5) Uani 1 1 d . . . . .
C115 C 0.6065(3) -0.0325(3) 0.38590(7) 0.0321(6) Uani 1 1 d . . . . .
O11 O 0.5884(3) -0.1765(3) 0.39672(6) 0.0543(6) Uani 1 1 d . . . . .
O12 O 0.5562(2) 0.1022(2) 0.40145(6) 0.0430(5) Uani 1 1 d . . . . .
H12 H 0.509859 0.072122 0.419196 0.065 Uiso 1 1 calc R U . . .
H22A H 0.352(4) -0.344(5) 0.4587(9) 0.043(9) Uiso 1 1 d . . . . .
H22B H 0.448(3) -0.247(4) 0.4346(8) 0.027(7) Uiso 1 1 d . . . . .
C21 C 0.3394(3) -0.1072(3) 0.46746(7) 0.0296(5) Uani 1 1 d . . . . .
C22 C 0.2354(3) -0.1112(4) 0.49417(7) 0.0339(6) Uani 1 1 d . . . . .
H22 H 0.19302 -0.216597 0.500942 0.041 Uiso 1 1 calc R U . . .
C23 C 0.1972(3) 0.0370(4) 0.50995(7) 0.0348(6) Uani 1 1 d . . . . .
H23 H 0.127079 0.037735 0.527776 0.042 Uiso 1 1 calc R U . . .
C24 C 0.2631(3) 0.1881(4) 0.49945(7) 0.0333(6) Uani 1 1 d . . . . .
C25 C 0.3617(3) 0.1854(4) 0.47294(7) 0.0332(6) Uani 1 1 d . . . . .
H25 H 0.404704 0.290035 0.465874 0.04 Uiso 1 1 calc R U . . .
N21 N 0.3987(2) 0.0419(3) 0.45697(6) 0.0314(5) Uani 1 1 d . . . . .
N22 N 0.3825(3) -0.2494(3) 0.45153(7) 0.0356(5) Uani 1 1 d . . . . .
N23 N 0.2253(3) 0.3482(3) 0.51531(6) 0.0416(6) Uani 1 1 d . . . . .
O21 O 0.2977(3) 0.4765(3) 0.50861(7) 0.0589(7) Uani 1 1 d . . . . .
O22 O 0.1230(3) 0.3502(3) 0.53535(6) 0.0536(6) Uani 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 1.372(5) . ?
C1 C2 1.374(4) . ?
C1 N1 1.481(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.95 . ?
C3 C4 1.364(4) . ?
C3 N2 1.468(5) . ?
C4 C5 1.382(5) . ?
C4 H4 0.95 . ?
C5 C6 1.371(5) . ?
C5 N3 1.470(4) . ?
C6 H6 0.95 . ?
N1 O1 1.208(4) . ?
N1 O2 1.221(4) . ?
N2 O4 1.209(4) . ?
N2 O3 1.223(5) . ?
N3 O5 1.222(6) . ?
N3 O6 1.231(6) . ?
C11 C12 1.404(4) . ?
C11 C114 1.406(4) . ?
C11 C115 1.502(3) . ?
C12 C17 1.429(4) . ?
C12 C13 1.429(4) . ?
C13 C14 1.354(5) . ?
C13 H13 0.95 . ?
C14 C15 1.404(6) . ?
C14 H14 0.95 . ?
C15 C16 1.346(6) . ?
C15 H15 0.95 . ?
C16 C17 1.429(4) . ?
C16 H16 0.95 . ?
C17 C18 1.391(5) . ?
C18 C19 1.381(4) . ?
C18 H18 0.95 . ?
C19 C110 1.421(4) . ?
C19 C114 1.440(4) . ?
C110 C111 1.337(5) . ?
C110 H110 0.95 . ?
C111 C112 1.416(5) . ?
C111 H111 0.95 . ?
C112 C113 1.360(5) . ?
C112 H112 0.95 . ?
C113 C114 1.423(4) . ?
C113 H113 0.95 . ?
C115 O11 1.211(3) . ?
C115 O12 1.298(3) . ?
O12 H12 0.84 . ?
C21 N22 1.331(4) . ?
C21 N21 1.352(3) . ?
C21 C22 1.416(3) . ?
C22 C23 1.354(4) . ?
C22 H22 0.95 . ?
C23 C24 1.391(4) . ?
C23 H23 0.95 . ?
C24 C25 1.376(4) . ?
C24 N23 1.435(4) . ?
C25 N21 1.323(3) . ?
C25 H25 0.95 . ?
N22 H22A 0.84(4) . ?
N22 H22B 0.90(3) . ?
N23 O22 1.228(3) . ?
N23 O21 1.231(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 123.1(3) . . ?
C6 C1 N1 119.2(3) . . ?
C2 C1 N1 117.7(3) . . ?
C1 C2 C3 116.4(3) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 123.8(3) . . ?
C4 C3 N2 117.8(3) . . ?
C2 C3 N2 118.4(3) . . ?
C3 C4 C5 116.4(3) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C6 C5 C4 123.2(3) . . ?
C6 C5 N3 118.2(4) . . ?
C4 C5 N3 118.6(4) . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 H6 121.5 . . ?
C1 C6 H6 121.5 . . ?
O1 N1 O2 124.6(3) . . ?
O1 N1 C1 117.6(3) . . ?
O2 N1 C1 117.6(3) . . ?
O4 N2 O3 124.4(4) . . ?
O4 N2 C3 118.2(3) . . ?
O3 N2 C3 117.3(3) . . ?
O5 N3 O6 125.1(4) . . ?
O5 N3 C5 117.8(4) . . ?
O6 N3 C5 117.1(4) . . ?
C12 C11 C114 121.4(2) . . ?
C12 C11 C115 118.3(2) . . ?
C114 C11 C115 120.3(2) . . ?
C11 C12 C17 119.1(2) . . ?
C11 C12 C13 123.1(2) . . ?
C17 C12 C13 117.8(2) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C12 119.3(3) . . ?
C18 C17 C16 122.1(3) . . ?
C12 C17 C16 118.6(3) . . ?
C19 C18 C17 122.3(3) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C110 121.8(3) . . ?
C18 C19 C114 119.4(3) . . ?
C110 C19 C114 118.7(3) . . ?
C111 C110 C19 121.5(3) . . ?
C111 C110 H110 119.3 . . ?
C19 C110 H110 119.3 . . ?
C110 C111 C112 120.3(3) . . ?
C110 C111 H111 119.8 . . ?
C112 C111 H111 119.8 . . ?
C113 C112 C111 120.8(3) . . ?
C113 C112 H112 119.6 . . ?
C111 C112 H112 119.6 . . ?
C112 C113 C114 120.8(3) . . ?
C112 C113 H113 119.6 . . ?
C114 C113 H113 119.6 . . ?
C11 C114 C113 123.6(2) . . ?
C11 C114 C19 118.6(2) . . ?
C113 C114 C19 117.8(3) . . ?
O11 C115 O12 123.1(2) . . ?
O11 C115 C11 122.2(2) . . ?
O12 C115 C11 114.6(2) . . ?
C115 O12 H12 109.5 . . ?
N22 C21 N21 117.2(2) . . ?
N22 C21 C22 121.6(2) . . ?
N21 C21 C22 121.2(2) . . ?
C23 C22 C21 119.2(2) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 118.5(2) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 N23 119.6(2) . . ?
C23 C24 N23 120.3(2) . . ?
N21 C25 C24 122.1(2) . . ?
N21 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
C25 N21 C21 118.9(2) . . ?
C21 N22 H22A 119(2) . . ?
C21 N22 H22B 121.8(18) . . ?
H22A N22 H22B 119(3) . . ?
O22 N23 O21 123.0(2) . . ?
O22 N23 C24 118.3(2) . . ?
O21 N23 C24 118.7(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 0.3(5) . . . . ?
N1 C1 C2 C3 -179.5(3) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C1 C2 C3 N2 -176.3(3) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
N2 C3 C4 C5 176.0(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 N3 -179.4(3) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
N3 C5 C6 C1 -179.4(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
N1 C1 C6 C5 178.7(3) . . . . ?
C6 C1 N1 O1 10.7(5) . . . . ?
C2 C1 N1 O1 -169.5(4) . . . . ?
C6 C1 N1 O2 -173.4(4) . . . . ?
C2 C1 N1 O2 6.4(5) . . . . ?
C4 C3 N2 O4 30.6(5) . . . . ?
C2 C3 N2 O4 -151.8(4) . . . . ?
C4 C3 N2 O3 -147.9(5) . . . . ?
C2 C3 N2 O3 29.7(6) . . . . ?
C6 C5 N3 O5 178.9(3) . . . . ?
C4 C5 N3 O5 -1.1(4) . . . . ?
C6 C5 N3 O6 -1.7(5) . . . . ?
C4 C5 N3 O6 178.3(3) . . . . ?
C114 C11 C12 C17 0.5(4) . . . . ?
C115 C11 C12 C17 179.9(2) . . . . ?
C114 C11 C12 C13 178.9(2) . . . . ?
C115 C11 C12 C13 -1.6(4) . . . . ?
C11 C12 C13 C14 -179.2(3) . . . . ?
C17 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C11 C12 C17 C18 -0.7(4) . . . . ?
C13 C12 C17 C18 -179.3(3) . . . . ?
C11 C12 C17 C16 179.5(3) . . . . ?
C13 C12 C17 C16 1.0(4) . . . . ?
C15 C16 C17 C18 179.6(3) . . . . ?
C15 C16 C17 C12 -0.7(5) . . . . ?
C12 C17 C18 C19 0.5(4) . . . . ?
C16 C17 C18 C19 -179.8(3) . . . . ?
C17 C18 C19 C110 179.0(3) . . . . ?
C17 C18 C19 C114 0.1(4) . . . . ?
C18 C19 C110 C111 -178.6(3) . . . . ?
C114 C19 C110 C111 0.4(5) . . . . ?
C19 C110 C111 C112 -1.1(5) . . . . ?
C110 C111 C112 C113 0.6(5) . . . . ?
C111 C112 C113 C114 0.7(5) . . . . ?
C12 C11 C114 C113 179.9(2) . . . . ?
C115 C11 C114 C113 0.4(4) . . . . ?
C12 C11 C114 C19 0.1(4) . . . . ?
C115 C11 C114 C19 -179.3(2) . . . . ?
C112 C113 C114 C11 178.8(3) . . . . ?
C112 C113 C114 C19 -1.4(4) . . . . ?
C18 C19 C114 C11 -0.4(4) . . . . ?
C110 C19 C114 C11 -179.4(2) . . . . ?
C18 C19 C114 C113 179.8(3) . . . . ?
C110 C19 C114 C113 0.9(4) . . . . ?
C12 C11 C115 O11 -59.2(4) . . . . ?
C114 C11 C115 O11 120.3(3) . . . . ?
C12 C11 C115 O12 118.9(3) . . . . ?
C114 C11 C115 O12 -61.7(3) . . . . ?
N22 C21 C22 C23 179.0(2) . . . . ?
N21 C21 C22 C23 -1.3(4) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C25 1.6(4) . . . . ?
C22 C23 C24 N23 179.7(2) . . . . ?
C23 C24 C25 N21 -0.8(4) . . . . ?
N23 C24 C25 N21 -178.9(2) . . . . ?
C24 C25 N21 C21 -1.1(4) . . . . ?
N22 C21 N21 C25 -178.1(2) . . . . ?
C22 C21 N21 C25 2.1(4) . . . . ?
C25 C24 N23 O22 170.8(3) . . . . ?
C23 C24 N23 O22 -7.2(4) . . . . ?
C25 C24 N23 O21 -10.0(4) . . . . ?
C23 C24 N23 O21 171.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O12 H12 N21 0.84 1.8 2.633(3) 171 . yes
N22 H22B O11 0.90(3) 2.04(3) 2.914(3) 165(3) . yes
N22 H22A O21 0.84(4) 2.40(4) 3.143(4) 149(3) 1_545 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_9
_audit_block_doi                 10.5517/ccdc.csd.cc1j2tcs
_database_code_depnum_ccdc_archive 'CCDC 1402885'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T08:41:23-00:00
_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 H10 O2, C6 H3 N3 O6, C5 H5 N3 O2'
_chemical_formula_sum            'C26 H18 N6 O10'
_chemical_formula_weight         574.46

#----------------------------------------------------------------------------#
#                   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                   21.0640(17)
_cell_length_b                   7.3594(5)
_cell_length_c                   17.0447(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.320(2)
_cell_angle_gamma                90
_cell_volume                     2444.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      28.23
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_T_max  0.9939
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.994

#----------------------------------------------------------------------------#
#                   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  0.0635
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_number            49213
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.384
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             4543
_reflns_number_gt                3386
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0434P)²+1.1296P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4543
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.191
_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 0.23034(9) 0.4888(2) 0.29261(11) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.24616(10) 0.5283(2) 0.37626(12) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.212694 0.574798 0.39575 0.034 Uiso 1 1 calc R U . . .
C3 C 0.31237(10) 0.4978(3) 0.43072(11) 0.0279(4) Uani 1 1 d . . . . .
C4 C 0.36247(10) 0.4301(2) 0.40484(11) 0.0286(4) Uani 1 1 d . . . . .
H4 H 0.408117 0.410157 0.443835 0.034 Uiso 1 1 calc R U . . .
C5 C 0.34298(9) 0.3932(2) 0.31998(11) 0.0266(4) Uani 1 1 d . . . . .
C6 C 0.27734(10) 0.4221(2) 0.26198(11) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.265112 0.396992 0.203384 0.033 Uiso 1 1 calc R U . . .
N1 N 0.15968(8) 0.5215(2) 0.23330(11) 0.0346(4) Uani 1 1 d . . . . .
N2 N 0.33110(9) 0.5403(2) 0.52047(10) 0.0395(4) Uani 1 1 d . . . . .
N3 N 0.39457(9) 0.3194(2) 0.29040(11) 0.0346(4) Uani 1 1 d . . . . .
O1 O 0.14242(8) 0.4604(2) 0.16208(9) 0.0452(4) Uani 1 1 d . . . . .
O2 O 0.12251(7) 0.6092(2) 0.25938(10) 0.0494(4) Uani 1 1 d . . . . .
O3 O 0.28492(9) 0.5784(3) 0.54371(10) 0.0642(5) Uani 1 1 d . . . . .
O4 O 0.39144(8) 0.5372(2) 0.56633(9) 0.0547(4) Uani 1 1 d . . . . .
O5 O 0.45073(8) 0.2830(2) 0.34361(10) 0.0476(4) Uani 1 1 d . . . . .
O6 O 0.37777(9) 0.2970(2) 0.21455(9) 0.0521(4) Uani 1 1 d . . . . .
C11 C 0.28221(9) 0.9416(2) 0.29640(10) 0.0223(4) Uani 1 1 d . . . . .
C12 C 0.26091(9) 1.0025(2) 0.36069(11) 0.0232(4) Uani 1 1 d . . . . .
C13 C 0.19342(9) 1.0641(2) 0.34535(12) 0.0266(4) Uani 1 1 d . . . . .
H13 H 0.160056 1.06372 0.289056 0.032 Uiso 1 1 calc R U . . .
C14 C 0.17569(10) 1.1235(3) 0.40924(12) 0.0327(4) Uani 1 1 d . . . . .
H14 H 0.130349 1.165971 0.397089 0.039 Uiso 1 1 calc R U . . .
C15 C 0.22368(11) 1.1231(3) 0.49386(13) 0.0374(5) Uani 1 1 d . . . . .
H15 H 0.210621 1.166126 0.538117 0.045 Uiso 1 1 calc R U . . .
C16 C 0.28787(11) 1.0618(3) 0.51186(12) 0.0350(5) Uani 1 1 d . . . . .
H16 H 0.319533 1.060068 0.569095 0.042 Uiso 1 1 calc R U . . .
C17 C 0.30911(9) 0.9997(2) 0.44660(11) 0.0272(4) Uani 1 1 d . . . . .
C18 C 0.37518(10) 0.9377(3) 0.46455(12) 0.0302(4) Uani 1 1 d . . . . .
H18 H 0.406785 0.935657 0.521813 0.036 Uiso 1 1 calc R U . . .
C19 C 0.39646(9) 0.8786(3) 0.40162(11) 0.0286(4) Uani 1 1 d . . . . .
C110 C 0.46447(10) 0.8150(3) 0.42037(13) 0.0374(5) Uani 1 1 d . . . . .
H110 H 0.495762 0.809234 0.477731 0.045 Uiso 1 1 calc R U . . .
C111 C 0.48521(10) 0.7630(3) 0.35820(14) 0.0427(5) Uani 1 1 d . . . . .
H111 H 0.530914 0.721793 0.371893 0.051 Uiso 1 1 calc R U . . .
C112 C 0.43932(11) 0.7695(3) 0.27293(13) 0.0399(5) Uani 1 1 d . . . . .
H112 H 0.454805 0.734665 0.22953 0.048 Uiso 1 1 calc R U . . .
C113 C 0.37381(10) 0.8242(3) 0.25171(12) 0.0315(4) Uani 1 1 d . . . . .
H113 H 0.34359 0.825102 0.19379 0.038 Uiso 1 1 calc R U . . .
C114 C 0.34950(9) 0.8806(2) 0.31498(11) 0.0244(4) Uani 1 1 d . . . . .
C115 C 0.23177(9) 0.9299(2) 0.20650(11) 0.0234(4) Uani 1 1 d . . . . .
O11 O 0.21954(7) 0.78819(17) 0.16762(8) 0.0321(3) Uani 1 1 d . . . . .
O12 O 0.20248(7) 1.08377(17) 0.17393(8) 0.0337(3) Uani 1 1 d . . . . .
H12 H 0.173161 1.065439 0.124911 0.051 Uiso 1 1 calc R U . . .
C21 C 0.08783(9) 0.9196(2) -0.03585(11) 0.0258(4) Uani 1 1 d . . . . .
C22 C 0.03044(9) 0.9326(2) -0.11318(11) 0.0246(4) Uani 1 1 d . . . . .
C23 C -0.00841(9) 1.0887(3) -0.13407(11) 0.0284(4) Uani 1 1 d . . . . .
H23 H -0.046072 1.097973 -0.186911 0.034 Uiso 1 1 calc R U . . .
C24 C 0.00782(9) 1.2307(3) -0.07785(12) 0.0304(4) Uani 1 1 d . . . . .
H24 H -0.017861 1.340382 -0.090622 0.036 Uiso 1 1 calc R U . . .
C25 C 0.06266(9) 1.2084(3) -0.00227(11) 0.0287(4) Uani 1 1 d . . . . .
H25 H 0.07312 1.304947 0.037648 0.034 Uiso 1 1 calc R U . . .
N21 N 0.10197(8) 1.0613(2) 0.01875(9) 0.0273(3) Uani 1 1 d . . . . .
N22 N 0.12961(9) 0.7775(3) -0.01142(12) 0.0382(4) Uani 1 1 d . . . . .
N23 N 0.00896(8) 0.7817(2) -0.17113(9) 0.0311(4) Uani 1 1 d . . . . .
O21 O 0.04437(8) 0.6441(2) -0.15681(9) 0.0453(4) Uani 1 1 d . . . . .
O22 O -0.04483(7) 0.7947(2) -0.23301(9) 0.0456(4) Uani 1 1 d . . . . .
H22A H 0.1610(12) 0.778(3) 0.0431(16) 0.050(7) Uiso 1 1 d . . . . .
H22B H 0.1226(11) 0.685(3) -0.0454(15) 0.046(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 C2 1.366(3) . ?
C1 C6 1.374(3) . ?
C1 N1 1.467(2) . ?
C2 C3 1.369(3) . ?
C2 H2 0.95 . ?
C3 C4 1.382(3) . ?
C3 N2 1.461(2) . ?
C4 C5 1.372(3) . ?
C4 H4 0.95 . ?
C5 C6 1.377(3) . ?
C5 N3 1.465(2) . ?
C6 H6 0.95 . ?
N1 O1 1.213(2) . ?
N1 O2 1.221(2) . ?
N2 O3 1.214(2) . ?
N2 O4 1.213(2) . ?
N3 O6 1.215(2) . ?
N3 O5 1.216(2) . ?
C11 C114 1.404(2) . ?
C11 C12 1.406(2) . ?
C11 C115 1.499(2) . ?
C12 C13 1.419(3) . ?
C12 C17 1.430(2) . ?
C13 C14 1.351(3) . ?
C13 H13 0.95 . ?
C14 C15 1.412(3) . ?
C14 H14 0.95 . ?
C15 C16 1.345(3) . ?
C15 H15 0.95 . ?
C16 C17 1.423(3) . ?
C16 H16 0.95 . ?
C17 C18 1.384(3) . ?
C18 C19 1.380(3) . ?
C18 H18 0.95 . ?
C19 C110 1.423(3) . ?
C19 C114 1.432(2) . ?
C110 C111 1.346(3) . ?
C110 H110 0.95 . ?
C111 C112 1.408(3) . ?
C111 H111 0.95 . ?
C112 C113 1.348(3) . ?
C112 H112 0.95 . ?
C113 C114 1.420(3) . ?
C113 H113 0.95 . ?
C115 O11 1.210(2) . ?
C115 O12 1.308(2) . ?
O12 H12 0.84 . ?
C21 N22 1.328(2) . ?
C21 N21 1.353(2) . ?
C21 C22 1.413(2) . ?
C22 C23 1.377(3) . ?
C22 N23 1.441(2) . ?
C23 C24 1.370(3) . ?
C23 H23 0.95 . ?
C24 C25 1.375(3) . ?
C24 H24 0.95 . ?
C25 N21 1.327(2) . ?
C25 H25 0.95 . ?
N22 H22A 0.91(2) . ?
N22 H22B 0.87(2) . ?
N23 O22 1.224(2) . ?
N23 O21 1.226(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 123.18(17) . . ?
C2 C1 N1 117.76(17) . . ?
C6 C1 N1 119.06(16) . . ?
C1 C2 C3 117.05(17) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C2 C3 C4 123.19(17) . . ?
C2 C3 N2 118.38(17) . . ?
C4 C3 N2 118.43(17) . . ?
C5 C4 C3 116.66(17) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C4 C5 C6 122.90(17) . . ?
C4 C5 N3 118.17(16) . . ?
C6 C5 N3 118.94(16) . . ?
C1 C6 C5 117.03(17) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
O1 N1 O2 124.74(17) . . ?
O1 N1 C1 117.96(17) . . ?
O2 N1 C1 117.30(16) . . ?
O3 N2 O4 124.54(17) . . ?
O3 N2 C3 117.37(17) . . ?
O4 N2 C3 118.09(17) . . ?
O6 N3 O5 124.85(17) . . ?
O6 N3 C5 117.52(16) . . ?
O5 N3 C5 117.62(16) . . ?
C114 C11 C12 121.33(15) . . ?
C114 C11 C115 118.38(15) . . ?
C12 C11 C115 120.19(15) . . ?
C11 C12 C13 123.53(16) . . ?
C11 C12 C17 118.73(16) . . ?
C13 C12 C17 117.73(16) . . ?
C14 C13 C12 121.29(17) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.85(18) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.07(18) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
C15 C16 C17 121.10(18) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 121.44(17) . . ?
C18 C17 C12 119.63(17) . . ?
C16 C17 C12 118.94(17) . . ?
C19 C18 C17 121.87(17) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C110 121.68(17) . . ?
C18 C19 C114 119.82(16) . . ?
C110 C19 C114 118.50(17) . . ?
C111 C110 C19 121.10(18) . . ?
C111 C110 H110 119.4 . . ?
C19 C110 H110 119.4 . . ?
C110 C111 C112 120.15(19) . . ?
C110 C111 H111 119.9 . . ?
C112 C111 H111 119.9 . . ?
C113 C112 C111 121.24(19) . . ?
C113 C112 H112 119.4 . . ?
C111 C112 H112 119.4 . . ?
C112 C113 C114 120.73(18) . . ?
C112 C113 H113 119.6 . . ?
C114 C113 H113 119.6 . . ?
C11 C114 C113 123.13(16) . . ?
C11 C114 C19 118.61(16) . . ?
C113 C114 C19 118.24(16) . . ?
O11 C115 O12 123.08(16) . . ?
O11 C115 C11 122.00(15) . . ?
O12 C115 C11 114.92(15) . . ?
C115 O12 H12 109.5 . . ?
N22 C21 N21 116.39(16) . . ?
N22 C21 C22 125.18(17) . . ?
N21 C21 C22 118.43(16) . . ?
C23 C22 C21 120.78(16) . . ?
C23 C22 N23 117.73(15) . . ?
C21 C22 N23 121.45(16) . . ?
C24 C23 C22 119.30(17) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 117.52(18) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 H24 121.2 . . ?
N21 C25 C24 124.49(18) . . ?
N21 C25 H25 117.8 . . ?
C24 C25 H25 117.8 . . ?
C25 N21 C21 119.41(15) . . ?
C21 N22 H22A 117.0(15) . . ?
C21 N22 H22B 118.9(15) . . ?
H22A N22 H22B 124(2) . . ?
O22 N23 O21 122.03(16) . . ?
O22 N23 C22 118.53(15) . . ?
O21 N23 C22 119.44(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 -0.3(3) . . . . ?
N1 C1 C2 C3 -179.73(16) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 N2 179.40(17) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
N2 C3 C4 C5 -179.52(17) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 N3 -179.34(16) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
N1 C1 C6 C5 -179.87(16) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
N3 C5 C6 C1 179.05(16) . . . . ?
C2 C1 N1 O1 -168.43(17) . . . . ?
C6 C1 N1 O1 12.1(2) . . . . ?
C2 C1 N1 O2 11.8(2) . . . . ?
C6 C1 N1 O2 -167.69(17) . . . . ?
C2 C3 N2 O3 9.2(3) . . . . ?
C4 C3 N2 O3 -171.29(19) . . . . ?
C2 C3 N2 O4 -169.94(19) . . . . ?
C4 C3 N2 O4 9.6(3) . . . . ?
C4 C5 N3 O6 -175.92(17) . . . . ?
C6 C5 N3 O6 4.2(3) . . . . ?
C4 C5 N3 O5 5.0(3) . . . . ?
C6 C5 N3 O5 -174.84(17) . . . . ?
C114 C11 C12 C13 -179.52(16) . . . . ?
C115 C11 C12 C13 -3.2(3) . . . . ?
C114 C11 C12 C17 -0.7(3) . . . . ?
C115 C11 C12 C17 175.60(15) . . . . ?
C11 C12 C13 C14 -179.19(17) . . . . ?
C17 C12 C13 C14 2.0(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C15 C16 C17 C18 179.56(19) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C11 C12 C17 C18 0.0(3) . . . . ?
C13 C12 C17 C18 178.93(17) . . . . ?
C11 C12 C17 C16 179.77(16) . . . . ?
C13 C12 C17 C16 -1.3(3) . . . . ?
C16 C17 C18 C19 -179.41(18) . . . . ?
C12 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C110 179.96(18) . . . . ?
C17 C18 C19 C114 0.0(3) . . . . ?
C18 C19 C110 C111 -178.0(2) . . . . ?
C114 C19 C110 C111 2.0(3) . . . . ?
C19 C110 C111 C112 -0.5(3) . . . . ?
C110 C111 C112 C113 -1.2(3) . . . . ?
C111 C112 C113 C114 1.3(3) . . . . ?
C12 C11 C114 C113 -177.63(17) . . . . ?
C115 C11 C114 C113 6.0(3) . . . . ?
C12 C11 C114 C19 1.0(3) . . . . ?
C115 C11 C114 C19 -175.38(16) . . . . ?
C112 C113 C114 C11 178.94(19) . . . . ?
C112 C113 C114 C19 0.3(3) . . . . ?
C18 C19 C114 C11 -0.6(3) . . . . ?
C110 C19 C114 C11 179.39(17) . . . . ?
C18 C19 C114 C113 178.06(17) . . . . ?
C110 C19 C114 C113 -1.9(3) . . . . ?
C114 C11 C115 O11 56.0(2) . . . . ?
C12 C11 C115 O11 -120.38(19) . . . . ?
C114 C11 C115 O12 -123.94(18) . . . . ?
C12 C11 C115 O12 59.7(2) . . . . ?
N22 C21 C22 C23 -177.68(18) . . . . ?
N21 C21 C22 C23 2.7(3) . . . . ?
N22 C21 C22 N23 4.8(3) . . . . ?
N21 C21 C22 N23 -174.80(15) . . . . ?
C21 C22 C23 C24 -1.9(3) . . . . ?
N23 C22 C23 C24 175.70(16) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C23 C24 C25 N21 2.0(3) . . . . ?
C24 C25 N21 C21 -1.2(3) . . . . ?
N22 C21 N21 C25 179.22(17) . . . . ?
C22 C21 N21 C25 -1.2(2) . . . . ?
C23 C22 N23 O22 -4.6(2) . . . . ?
C21 C22 N23 O22 172.97(16) . . . . ?
C23 C22 N23 O21 176.11(16) . . . . ?
C21 C22 N23 O21 -6.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O12 H12 N21 0.84 1.86 2.6929(19) 171 . yes
N22 H22A O11 0.91(2) 2.01(3) 2.918(2) 172(2) . yes
N22 H22B O21 0.87(2) 2.01(2) 2.636(2) 128(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_7
_audit_block_doi                 10.5517/ccdc.csd.cc1j2t9q
_database_code_depnum_ccdc_archive 'CCDC 1402883'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T08:10:34-00:00
_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 H10 O2, C6 H3 N3 O6, C5 H5 Br N2'
_chemical_formula_sum            'C26 H18 Br N5 O8'
_chemical_formula_weight         608.36

#----------------------------------------------------------------------------#
#                   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                   8.9784(15)
_cell_length_b                   7.2372(12)
_cell_length_c                   38.160(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.321(4)
_cell_angle_gamma                90
_cell_volume                     2472.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      28.24
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.124
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    1.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.5707
_exptl_absorpt_correction_T_max  0.8145
_shelx_estimated_absorpt_T_min   0.571
_shelx_estimated_absorpt_T_max   0.814

#----------------------------------------------------------------------------#
#                   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  0.0486
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_number            28820
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.865
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4588
_reflns_number_gt                4123
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0758P)²+1.6976P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4588
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.09

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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 1.0632(3) 0.3845(4) 0.18199(6) 0.0280(5) Uani 1 1 d . . . . .
C2 C 1.1295(3) 0.4381(4) 0.15205(7) 0.0282(5) Uani 1 1 d . . . . .
H2 H 1.233225 0.464556 0.152206 0.034 Uiso 1 1 calc R U . . .
C3 C 1.0347(3) 0.4505(3) 0.12189(6) 0.0264(5) Uani 1 1 d . . . . .
C4 C 0.8841(3) 0.4182(4) 0.12063(6) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.822487 0.430175 0.099399 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8261(3) 0.3673(3) 0.15176(7) 0.0268(5) Uani 1 1 d . . . . .
C6 C 0.9136(3) 0.3473(3) 0.18282(7) 0.0290(6) Uani 1 1 d . . . . .
H6 H 0.87215 0.309409 0.203845 0.035 Uiso 1 1 calc R U . . .
N1 N 1.1590(3) 0.3695(4) 0.21484(6) 0.0423(6) Uani 1 1 d . . . . .
N2 N 1.1022(3) 0.5011(3) 0.08896(6) 0.0346(5) Uani 1 1 d . . . . .
N3 N 0.6640(3) 0.3378(3) 0.15180(6) 0.0345(5) Uani 1 1 d . . . . .
O1 O 1.1028(3) 0.3141(5) 0.24067(6) 0.0661(8) Uani 1 1 d . . . . .
O2 O 1.2896(3) 0.4116(5) 0.21399(7) 0.0739(9) Uani 1 1 d . . . . .
O3 O 1.2298(3) 0.5571(3) 0.09092(6) 0.0508(6) Uani 1 1 d . . . . .
O4 O 1.0244(3) 0.4797(3) 0.06157(5) 0.0486(6) Uani 1 1 d . . . . .
O5 O 0.5853(2) 0.3995(3) 0.12719(6) 0.0440(5) Uani 1 1 d . . . . .
O6 O 0.6190(2) 0.2546(3) 0.17678(6) 0.0486(6) Uani 1 1 d . . . . .
C11 C 0.8834(3) 0.8975(3) 0.13525(6) 0.0203(5) Uani 1 1 d . . . . .
C12 C 0.8389(3) 0.8368(3) 0.16783(6) 0.0234(5) Uani 1 1 d . . . . .
C13 C 0.6899(3) 0.7793(4) 0.17266(7) 0.0290(5) Uani 1 1 d . . . . .
H13 H 0.614866 0.790677 0.153855 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6542(4) 0.7082(4) 0.20406(7) 0.0379(7) Uani 1 1 d . . . . .
H14 H 0.554842 0.668826 0.206897 0.045 Uiso 1 1 calc R U . . .
C15 C 0.7642(4) 0.6928(4) 0.23235(7) 0.0429(8) Uani 1 1 d . . . . .
H15 H 0.738654 0.63897 0.2538 0.051 Uiso 1 1 calc R U . . .
C16 C 0.9043(4) 0.7530(4) 0.22948(7) 0.0394(7) Uani 1 1 d . . . . .
H16 H 0.974998 0.746869 0.249274 0.047 Uiso 1 1 calc R U . . .
C17 C 0.9485(3) 0.8262(3) 0.19703(6) 0.0287(6) Uani 1 1 d . . . . .
C18 C 1.0948(3) 0.8799(4) 0.19276(7) 0.0338(6) Uani 1 1 d . . . . .
H18 H 1.166428 0.875808 0.212381 0.041 Uiso 1 1 calc R U . . .
C19 C 1.1389(3) 0.9398(4) 0.16032(7) 0.0297(6) Uani 1 1 d . . . . .
C110 C 1.2893(3) 0.9936(4) 0.15538(9) 0.0418(7) Uani 1 1 d . . . . .
H110 H 1.361953 0.990944 0.174814 0.05 Uiso 1 1 calc R U . . .
C111 C 1.3298(3) 1.0478(4) 0.12373(10) 0.0460(8) Uani 1 1 d . . . . .
H111 H 1.430415 1.08173 0.120972 0.055 Uiso 1 1 calc R U . . .
C112 C 1.2229(3) 1.0544(4) 0.09454(8) 0.0378(7) Uani 1 1 d . . . . .
H112 H 1.252538 1.09339 0.072332 0.045 Uiso 1 1 calc R U . . .
C113 C 1.0790(3) 1.0059(4) 0.09783(7) 0.0285(5) Uani 1 1 d . . . . .
H113 H 1.009147 1.011315 0.077887 0.034 Uiso 1 1 calc R U . . .
C114 C 1.0307(3) 0.9466(3) 0.13083(6) 0.0236(5) Uani 1 1 d . . . . .
C115 C 0.7695(3) 0.9064(3) 0.10422(6) 0.0213(5) Uani 1 1 d . . . . .
O11 O 0.6825(2) 1.0326(3) 0.10016(5) 0.0352(4) Uani 1 1 d . . . . .
O12 O 0.7784(2) 0.7680(3) 0.08285(5) 0.0337(4) Uani 1 1 d . . . . .
H12 H 0.702(4) 0.772(5) 0.0631(9) 0.047(9) Uiso 1 1 d . . . . .
C21 C 0.6537(3) 0.6904(3) -0.00064(6) 0.0225(5) Uani 1 1 d . . . . .
C22 C 0.5610(3) 0.6742(3) -0.03209(6) 0.0258(5) Uani 1 1 d . . . . .
H22 H 0.600332 0.627938 -0.052787 0.031 Uiso 1 1 calc R U . . .
C23 C 0.4544(3) 0.8068(3) 0.02794(6) 0.0244(5) Uani 1 1 d . . . . .
H23 H 0.416694 0.85195 0.048907 0.029 Uiso 1 1 calc R U . . .
C24 C 0.3601(3) 0.7931(4) -0.00189(7) 0.0251(5) Uani 1 1 d . . . . .
C25 C 0.4156(3) 0.7252(4) -0.03251(6) 0.0276(5) Uani 1 1 d . . . . .
H25 H 0.352046 0.714738 -0.053478 0.033 Uiso 1 1 calc R U . . .
N21 N 0.5979(2) 0.7584(3) 0.02828(5) 0.0235(4) Uani 1 1 d . . . . .
N22 N 0.7984(3) 0.6422(3) 0.00143(7) 0.0315(5) Uani 1 1 d . . . . .
Br21 Br 0.15651(3) 0.85719(4) -0.00131(2) 0.03912(13) Uani 1 1 d . . . . .
H22A H 0.836(4) 0.583(5) -0.0159(9) 0.041(9) Uiso 1 1 d . . . . .
H22B H 0.848(4) 0.622(5) 0.0232(10) 0.047(10) 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 1.373(4) . ?
C1 C2 1.383(4) . ?
C1 N1 1.470(3) . ?
C2 C3 1.382(4) . ?
C2 H2 0.95 . ?
C3 C4 1.370(4) . ?
C3 N2 1.481(3) . ?
C4 C5 1.382(4) . ?
C4 H4 0.95 . ?
C5 C6 1.379(4) . ?
C5 N3 1.471(4) . ?
C6 H6 0.95 . ?
N1 O1 1.209(4) . ?
N1 O2 1.215(4) . ?
N2 O3 1.212(3) . ?
N2 O4 1.222(3) . ?
N3 O5 1.217(3) . ?
N3 O6 1.222(3) . ?
C11 C114 1.392(3) . ?
C11 C12 1.405(3) . ?
C11 C115 1.506(3) . ?
C12 C13 1.426(4) . ?
C12 C17 1.432(4) . ?
C13 C14 1.364(4) . ?
C13 H13 0.95 . ?
C14 C15 1.412(5) . ?
C14 H14 0.95 . ?
C15 C16 1.344(5) . ?
C15 H15 0.95 . ?
C16 C17 1.430(4) . ?
C16 H16 0.95 . ?
C17 C18 1.391(4) . ?
C18 C19 1.397(4) . ?
C18 H18 0.95 . ?
C19 C114 1.431(4) . ?
C19 C110 1.431(4) . ?
C110 C111 1.346(5) . ?
C110 H110 0.95 . ?
C111 C112 1.415(5) . ?
C111 H111 0.95 . ?
C112 C113 1.353(4) . ?
C112 H112 0.95 . ?
C113 C114 1.429(3) . ?
C113 H113 0.95 . ?
C115 O11 1.204(3) . ?
C115 O12 1.298(3) . ?
O12 H12 0.98(3) . ?
C21 N21 1.339(3) . ?
C21 N22 1.342(3) . ?
C21 C22 1.413(3) . ?
C22 C25 1.356(4) . ?
C22 H22 0.95 . ?
C23 N21 1.334(3) . ?
C23 C24 1.370(3) . ?
C23 H23 0.95 . ?
C24 C25 1.393(4) . ?
C24 Br21 1.888(2) . ?
C25 H25 0.95 . ?
N22 H22A 0.88(4) . ?
N22 H22B 0.92(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 123.9(2) . . ?
C6 C1 N1 118.5(2) . . ?
C2 C1 N1 117.7(2) . . ?
C3 C2 C1 115.4(2) . . ?
C3 C2 H2 122.3 . . ?
C1 C2 H2 122.3 . . ?
C4 C3 C2 124.2(2) . . ?
C4 C3 N2 118.6(2) . . ?
C2 C3 N2 117.2(2) . . ?
C3 C4 C5 116.8(2) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 N3 118.9(2) . . ?
C4 C5 N3 118.4(2) . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
O1 N1 O2 124.6(3) . . ?
O1 N1 C1 117.8(3) . . ?
O2 N1 C1 117.6(3) . . ?
O3 N2 O4 124.9(2) . . ?
O3 N2 C3 118.4(2) . . ?
O4 N2 C3 116.8(2) . . ?
O5 N3 O6 125.2(3) . . ?
O5 N3 C5 117.6(2) . . ?
O6 N3 C5 117.2(2) . . ?
C114 C11 C12 121.6(2) . . ?
C114 C11 C115 119.2(2) . . ?
C12 C11 C115 119.2(2) . . ?
C11 C12 C13 122.5(2) . . ?
C11 C12 C17 118.7(2) . . ?
C13 C12 C17 118.7(2) . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 122.1(3) . . ?
C18 C17 C12 119.6(2) . . ?
C16 C17 C12 118.3(3) . . ?
C17 C18 C19 121.6(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C114 119.1(2) . . ?
C18 C19 C110 122.3(3) . . ?
C114 C19 C110 118.6(3) . . ?
C111 C110 C19 121.2(3) . . ?
C111 C110 H110 119.4 . . ?
C19 C110 H110 119.4 . . ?
C110 C111 C112 120.2(3) . . ?
C110 C111 H111 119.9 . . ?
C112 C111 H111 119.9 . . ?
C113 C112 C111 120.9(3) . . ?
C113 C112 H112 119.6 . . ?
C111 C112 H112 119.6 . . ?
C112 C113 C114 121.0(3) . . ?
C112 C113 H113 119.5 . . ?
C114 C113 H113 119.5 . . ?
C11 C114 C113 122.6(2) . . ?
C11 C114 C19 119.4(2) . . ?
C113 C114 C19 118.0(2) . . ?
O11 C115 O12 125.1(2) . . ?
O11 C115 C11 121.9(2) . . ?
O12 C115 C11 113.0(2) . . ?
C115 O12 H12 113(2) . . ?
N21 C21 N22 117.9(2) . . ?
N21 C21 C22 119.8(2) . . ?
N22 C21 C22 122.3(2) . . ?
C25 C22 C21 119.5(2) . . ?
C25 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N21 C23 C24 121.7(2) . . ?
N21 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C25 119.0(2) . . ?
C23 C24 Br21 120.71(19) . . ?
C25 C24 Br21 120.27(18) . . ?
C22 C25 C24 119.4(2) . . ?
C22 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C23 N21 C21 120.6(2) . . ?
C21 N22 H22A 121(2) . . ?
C21 N22 H22B 120(2) . . ?
H22A N22 H22B 114(3) . . ?

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 -0.8(4) . . . . ?
N1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
C1 C2 C3 N2 -177.9(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
N2 C3 C4 C5 178.6(2) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C3 C4 C5 N3 177.9(2) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
N1 C1 C6 C5 178.4(2) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
N3 C5 C6 C1 -177.0(2) . . . . ?
C6 C1 N1 O1 4.4(4) . . . . ?
C2 C1 N1 O1 -176.5(3) . . . . ?
C6 C1 N1 O2 -176.5(3) . . . . ?
C2 C1 N1 O2 2.6(4) . . . . ?
C4 C3 N2 O3 168.8(2) . . . . ?
C2 C3 N2 O3 -11.5(3) . . . . ?
C4 C3 N2 O4 -12.4(3) . . . . ?
C2 C3 N2 O4 167.2(2) . . . . ?
C6 C5 N3 O5 162.0(2) . . . . ?
C4 C5 N3 O5 -16.6(3) . . . . ?
C6 C5 N3 O6 -17.3(3) . . . . ?
C4 C5 N3 O6 164.1(2) . . . . ?
C114 C11 C12 C13 -177.6(2) . . . . ?
C115 C11 C12 C13 1.3(3) . . . . ?
C114 C11 C12 C17 0.2(3) . . . . ?
C115 C11 C12 C17 179.0(2) . . . . ?
C11 C12 C13 C14 175.0(2) . . . . ?
C17 C12 C13 C14 -2.8(4) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 C16 2.2(4) . . . . ?
C14 C15 C16 C17 -3.2(4) . . . . ?
C15 C16 C17 C18 -176.4(3) . . . . ?
C15 C16 C17 C12 1.1(4) . . . . ?
C11 C12 C17 C18 1.5(4) . . . . ?
C13 C12 C17 C18 179.4(2) . . . . ?
C11 C12 C17 C16 -176.0(2) . . . . ?
C13 C12 C17 C16 1.8(3) . . . . ?
C16 C17 C18 C19 175.7(2) . . . . ?
C12 C17 C18 C19 -1.7(4) . . . . ?
C17 C18 C19 C114 0.3(4) . . . . ?
C17 C18 C19 C110 -179.3(3) . . . . ?
C18 C19 C110 C111 178.8(3) . . . . ?
C114 C19 C110 C111 -0.7(4) . . . . ?
C19 C110 C111 C112 0.6(5) . . . . ?
C110 C111 C112 C113 -0.3(4) . . . . ?
C111 C112 C113 C114 0.0(4) . . . . ?
C12 C11 C114 C113 179.0(2) . . . . ?
C115 C11 C114 C113 0.1(3) . . . . ?
C12 C11 C114 C19 -1.6(3) . . . . ?
C115 C11 C114 C19 179.5(2) . . . . ?
C112 C113 C114 C11 179.3(2) . . . . ?
C112 C113 C114 C19 -0.1(4) . . . . ?
C18 C19 C114 C11 1.4(3) . . . . ?
C110 C19 C114 C11 -179.0(2) . . . . ?
C18 C19 C114 C113 -179.1(2) . . . . ?
C110 C19 C114 C113 0.4(3) . . . . ?
C114 C11 C115 O11 -101.4(3) . . . . ?
C12 C11 C115 O11 79.7(3) . . . . ?
C114 C11 C115 O12 77.5(3) . . . . ?
C12 C11 C115 O12 -101.4(3) . . . . ?
N21 C21 C22 C25 -1.0(4) . . . . ?
N22 C21 C22 C25 180.0(2) . . . . ?
N21 C23 C24 C25 0.6(4) . . . . ?
N21 C23 C24 Br21 178.52(19) . . . . ?
C21 C22 C25 C24 0.1(4) . . . . ?
C23 C24 C25 C22 0.1(4) . . . . ?
Br21 C24 C25 C22 -177.85(19) . . . . ?
C24 C23 N21 C21 -1.5(4) . . . . ?
N22 C21 N21 C23 -179.3(2) . . . . ?
C22 C21 N21 C23 1.7(4) . . . . ?

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
O12 H12 N21 0.98(3) 1.57(3) 2.542(3) 171(3) . yes
N22 H22A O4 0.88(4) 2.27(4) 3.109(3) 161(3) 3_765 yes
N22 H22B O4 0.92(4) 2.31(4) 3.173(3) 154(3) . yes
N22 H22B O12 0.92(4) 2.63(4) 3.255(3) 125(3) . 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_6
_audit_block_doi                 10.5517/ccdc.csd.cc1j2t8p
_database_code_depnum_ccdc_archive 'CCDC 1402882'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T07:55:42-00:00
_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 H10 O2, C6 H3 N3 O6, C5 H5 Br N2'
_chemical_formula_sum            'C26 H18 Br N5 O8'
_chemical_formula_weight         608.36

#----------------------------------------------------------------------------#
#                   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                   21.301(5)
_cell_length_b                   7.2862(13)
_cell_length_c                   17.188(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.047(5)
_cell_angle_gamma                90
_cell_volume                     2454.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      23.53
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.6417
_exptl_absorpt_correction_T_max  0.9337
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.934

#----------------------------------------------------------------------------#
#                   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  0.1353
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_number            52199
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.983
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4560
_reflns_number_gt                2943
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0643P)²+2.2812P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4560
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.09

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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 0.1829(2) 0.5046(5) 0.0712(3) 0.0270(10) Uani 1 1 d . . . . .
C2 C 0.1328(2) 0.5684(5) 0.0964(3) 0.0293(10) Uani 1 1 d . . . . .
H2 H 0.087486 0.589246 0.056896 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1518(2) 0.6005(5) 0.1817(3) 0.0245(10) Uani 1 1 d . . . . .
C4 C 0.2164(2) 0.5719(5) 0.2395(3) 0.0263(10) Uani 1 1 d . . . . .
H4 H 0.228196 0.594718 0.297968 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2641(2) 0.5086(5) 0.2102(3) 0.0257(10) Uani 1 1 d . . . . .
C6 C 0.2485(2) 0.4736(5) 0.1263(3) 0.0279(10) Uani 1 1 d . . . . .
H6 H 0.282077 0.429659 0.107238 0.033 Uiso 1 1 calc R U . . .
N1 N 0.1647(2) 0.4651(5) -0.0189(2) 0.0417(10) Uani 1 1 d . . . . .
N2 N 0.1002(2) 0.6703(5) 0.2102(3) 0.0333(9) Uani 1 1 d . . . . .
N3 N 0.3344(2) 0.4778(5) 0.2701(2) 0.0363(9) Uani 1 1 d . . . . .
O1 O 0.2107(2) 0.4254(6) -0.0407(2) 0.0662(12) Uani 1 1 d . . . . .
O2 O 0.10417(18) 0.4700(5) -0.0661(2) 0.0554(10) Uani 1 1 d . . . . .
O3 O 0.04439(17) 0.7101(5) 0.1573(2) 0.0464(9) Uani 1 1 d . . . . .
O4 O 0.11573(18) 0.6855(5) 0.2865(2) 0.0506(9) Uani 1 1 d . . . . .
O5 O 0.35021(16) 0.5267(4) 0.34291(19) 0.0406(8) Uani 1 1 d . . . . .
O6 O 0.37380(17) 0.4031(5) 0.2435(2) 0.0538(10) Uani 1 1 d . . . . .
C11 C 0.2214(2) 0.0455(5) 0.2089(2) 0.0231(9) Uani 1 1 d . . . . .
C12 C 0.2444(2) -0.0106(5) 0.1465(2) 0.0231(10) Uani 1 1 d . . . . .
C13 C 0.3124(2) -0.0705(5) 0.1642(3) 0.0279(10) Uani 1 1 d . . . . .
H13 H 0.344712 -0.073325 0.220989 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3313(2) -0.1231(6) 0.1014(3) 0.0350(11) Uani 1 1 d . . . . .
H14 H 0.376739 -0.164261 0.114985 0.042 Uiso 1 1 calc R U . . .
C15 C 0.2852(2) -0.1185(6) 0.0156(3) 0.0392(12) Uani 1 1 d . . . . .
H15 H 0.299752 -0.155645 -0.027664 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2208(2) -0.0614(6) -0.0043(3) 0.0375(12) Uani 1 1 d . . . . .
H16 H 0.190029 -0.058431 -0.06195 0.045 Uiso 1 1 calc R U . . .
C17 C 0.1978(2) -0.0052(5) 0.0597(3) 0.0263(10) Uani 1 1 d . . . . .
C18 C 0.1313(2) 0.0548(6) 0.0393(3) 0.0317(11) Uani 1 1 d . . . . .
H18 H 0.100872 0.059181 -0.018464 0.038 Uiso 1 1 calc R U . . .
C19 C 0.1082(2) 0.1080(5) 0.1004(2) 0.0254(10) Uani 1 1 d . . . . .
C110 C 0.0401(2) 0.1725(6) 0.0786(3) 0.0355(11) Uani 1 1 d . . . . .
H110 H 0.010125 0.181817 0.020817 0.043 Uiso 1 1 calc R U . . .
C111 C 0.0180(2) 0.2204(6) 0.1399(3) 0.0411(12) Uani 1 1 d . . . . .
H111 H -0.027622 0.260947 0.124657 0.049 Uiso 1 1 calc R U . . .
C112 C 0.0620(2) 0.2107(6) 0.2258(3) 0.0394(12) Uani 1 1 d . . . . .
H112 H 0.045402 0.242801 0.267815 0.047 Uiso 1 1 calc R U . . .
C113 C 0.1278(2) 0.1562(6) 0.2494(3) 0.0323(11) Uani 1 1 d . . . . .
H113 H 0.156785 0.152431 0.307723 0.039 Uiso 1 1 calc R U . . .
C114 C 0.1541(2) 0.1047(5) 0.1880(2) 0.0247(10) Uani 1 1 d . . . . .
C115 C 0.2702(2) 0.0566(6) 0.2999(2) 0.0262(10) Uani 1 1 d . . . . .
O11 O 0.28072(15) 0.1990(4) 0.33938(17) 0.0337(8) Uani 1 1 d . . . . .
O12 O 0.29976(16) -0.0989(4) 0.33271(19) 0.0368(8) Uani 1 1 d . . . . .
H12 H 0.339(3) -0.087(9) 0.386(4) 0.11(3) Uiso 1 1 d . . . . .
C21 C 0.4146(2) 0.0606(6) 0.5392(3) 0.0270(10) Uani 1 1 d . . . . .
C22 C 0.4746(2) 0.0519(6) 0.6121(2) 0.0290(10) Uani 1 1 d . . . . .
C23 C 0.5152(2) -0.0997(6) 0.6294(3) 0.0316(11) Uani 1 1 d . . . . .
H23 H 0.555268 -0.105941 0.67975 0.038 Uiso 1 1 calc R U . . .
C24 C 0.4975(2) -0.2438(6) 0.5730(3) 0.0321(10) Uani 1 1 d . . . . .
H24 H 0.524772 -0.351418 0.583716 0.038 Uiso 1 1 calc R U . . .
C25 C 0.4394(2) -0.2272(6) 0.5011(3) 0.0309(10) Uani 1 1 d . . . . .
H25 H 0.427388 -0.324987 0.461325 0.037 Uiso 1 1 calc R U . . .
Br1 Br 0.50116(2) 0.25838(7) 0.68461(3) 0.04272(19) Uani 1 1 d . . . . .
N21 N 0.39824(17) -0.0785(4) 0.4839(2) 0.0269(8) Uani 1 1 d . . . . .
N22 N 0.3718(2) 0.2056(6) 0.5195(3) 0.0435(12) Uani 1 1 d . . . . .
H22A H 0.341(2) 0.209(6) 0.474(3) 0.029(13) Uiso 1 1 d . . . . .
H22B H 0.381(2) 0.285(6) 0.550(3) 0.033(15) 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 1.365(6) . ?
C1 C2 1.381(6) . ?
C1 N1 1.469(5) . ?
C2 C3 1.381(6) . ?
C2 H2 0.95 . ?
C3 C4 1.362(6) . ?
C3 N2 1.459(5) . ?
C4 C5 1.377(6) . ?
C4 H4 0.95 . ?
C5 C6 1.372(6) . ?
C5 N3 1.466(5) . ?
C6 H6 0.95 . ?
N1 O1 1.214(5) . ?
N1 O2 1.226(5) . ?
N2 O3 1.215(5) . ?
N2 O4 1.224(5) . ?
N3 O5 1.215(4) . ?
N3 O6 1.229(5) . ?
C11 C12 1.401(6) . ?
C11 C114 1.404(6) . ?
C11 C115 1.504(5) . ?
C12 C13 1.427(6) . ?
C12 C17 1.433(5) . ?
C13 C14 1.348(6) . ?
C13 H13 0.95 . ?
C14 C15 1.416(6) . ?
C14 H14 0.95 . ?
C15 C16 1.344(6) . ?
C15 H15 0.95 . ?
C16 C17 1.429(6) . ?
C16 H16 0.95 . ?
C17 C18 1.389(6) . ?
C18 C19 1.379(6) . ?
C18 H18 0.95 . ?
C19 C110 1.428(6) . ?
C19 C114 1.438(5) . ?
C110 C111 1.357(7) . ?
C110 H110 0.95 . ?
C111 C112 1.406(7) . ?
C111 H111 0.95 . ?
C112 C113 1.357(6) . ?
C112 H112 0.95 . ?
C113 C114 1.425(6) . ?
C113 H113 0.95 . ?
C115 O11 1.211(5) . ?
C115 O12 1.312(5) . ?
O12 H12 0.97(7) . ?
C21 N21 1.339(5) . ?
C21 N22 1.349(6) . ?
C21 C22 1.397(6) . ?
C22 C23 1.361(6) . ?
C22 Br1 1.893(4) . ?
C23 C24 1.377(6) . ?
C23 H23 0.95 . ?
C24 C25 1.371(6) . ?
C24 H24 0.95 . ?
C25 N21 1.351(5) . ?
C25 H25 0.95 . ?
N22 H22A 0.81(5) . ?
N22 H22B 0.75(5) . ?

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 123.0(4) . . ?
C6 C1 N1 118.4(4) . . ?
C2 C1 N1 118.6(4) . . ?
C3 C2 C1 116.7(4) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C4 C3 C2 122.8(4) . . ?
C4 C3 N2 119.2(4) . . ?
C2 C3 N2 118.1(4) . . ?
C3 C4 C5 117.6(4) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 122.5(4) . . ?
C6 C5 N3 118.0(4) . . ?
C4 C5 N3 119.4(4) . . ?
C1 C6 C5 117.3(4) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
O1 N1 O2 124.7(4) . . ?
O1 N1 C1 117.3(4) . . ?
O2 N1 C1 117.9(4) . . ?
O3 N2 O4 123.8(4) . . ?
O3 N2 C3 118.4(4) . . ?
O4 N2 C3 117.8(4) . . ?
O5 N3 O6 124.0(4) . . ?
O5 N3 C5 118.2(4) . . ?
O6 N3 C5 117.7(4) . . ?
C12 C11 C114 121.4(4) . . ?
C12 C11 C115 120.5(4) . . ?
C114 C11 C115 118.0(4) . . ?
C11 C12 C13 123.7(4) . . ?
C11 C12 C17 118.8(4) . . ?
C13 C12 C17 117.5(4) . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.1(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 C12 119.6(4) . . ?
C16 C17 C12 119.2(4) . . ?
C19 C18 C17 121.9(4) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C110 121.4(4) . . ?
C18 C19 C114 119.6(4) . . ?
C110 C19 C114 119.0(4) . . ?
C111 C110 C19 120.4(4) . . ?
C111 C110 H110 119.8 . . ?
C19 C110 H110 119.8 . . ?
C110 C111 C112 120.7(4) . . ?
C110 C111 H111 119.6 . . ?
C112 C111 H111 119.6 . . ?
C113 C112 C111 121.0(5) . . ?
C113 C112 H112 119.5 . . ?
C111 C112 H112 119.5 . . ?
C112 C113 C114 120.9(4) . . ?
C112 C113 H113 119.5 . . ?
C114 C113 H113 119.5 . . ?
C11 C114 C113 123.3(4) . . ?
C11 C114 C19 118.7(4) . . ?
C113 C114 C19 117.9(4) . . ?
O11 C115 O12 123.1(4) . . ?
O11 C115 C11 122.0(4) . . ?
O12 C115 C11 114.8(4) . . ?
C115 O12 H12 115(4) . . ?
N21 C21 N22 116.9(4) . . ?
N21 C21 C22 119.7(4) . . ?
N22 C21 C22 123.5(4) . . ?
C23 C22 C21 120.8(4) . . ?
C23 C22 Br1 120.0(3) . . ?
C21 C22 Br1 119.1(3) . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 118.0(4) . . ?
C25 C24 H24 121 . . ?
C23 C24 H24 121 . . ?
N21 C25 C24 123.2(4) . . ?
N21 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?
C21 N21 C25 119.0(3) . . ?
C21 N22 H22A 119(3) . . ?
C21 N22 H22B 117(4) . . ?
H22A N22 H22B 123(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
C6 C1 C2 C3 -0.1(6) . . . . ?
N1 C1 C2 C3 178.8(4) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C1 C2 C3 N2 179.2(4) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
N2 C3 C4 C5 -179.0(3) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C3 C4 C5 N3 179.4(3) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
N1 C1 C6 C5 -178.9(4) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
N3 C5 C6 C1 -179.4(3) . . . . ?
C6 C1 N1 O1 -7.6(6) . . . . ?
C2 C1 N1 O1 173.4(4) . . . . ?
C6 C1 N1 O2 170.6(4) . . . . ?
C2 C1 N1 O2 -8.4(6) . . . . ?
C4 C3 N2 O3 173.8(4) . . . . ?
C2 C3 N2 O3 -5.5(5) . . . . ?
C4 C3 N2 O4 -6.2(6) . . . . ?
C2 C3 N2 O4 174.6(4) . . . . ?
C6 C5 N3 O5 172.3(4) . . . . ?
C4 C5 N3 O5 -7.4(6) . . . . ?
C6 C5 N3 O6 -7.9(6) . . . . ?
C4 C5 N3 O6 172.4(4) . . . . ?
C114 C11 C12 C13 179.5(4) . . . . ?
C115 C11 C12 C13 3.9(6) . . . . ?
C114 C11 C12 C17 0.6(6) . . . . ?
C115 C11 C12 C17 -175.0(4) . . . . ?
C11 C12 C13 C14 179.9(4) . . . . ?
C17 C12 C13 C14 -1.2(6) . . . . ?
C12 C13 C14 C15 1.0(6) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C15 C16 C17 C18 179.7(4) . . . . ?
C15 C16 C17 C12 -0.2(6) . . . . ?
C11 C12 C17 C18 -0.1(6) . . . . ?
C13 C12 C17 C18 -179.0(4) . . . . ?
C11 C12 C17 C16 179.7(4) . . . . ?
C13 C12 C17 C16 0.8(6) . . . . ?
C16 C17 C18 C19 179.5(4) . . . . ?
C12 C17 C18 C19 -0.7(6) . . . . ?
C17 C18 C19 C110 178.9(4) . . . . ?
C17 C18 C19 C114 0.9(6) . . . . ?
C18 C19 C110 C111 178.5(4) . . . . ?
C114 C19 C110 C111 -3.5(6) . . . . ?
C19 C110 C111 C112 1.1(7) . . . . ?
C110 C111 C112 C113 1.1(7) . . . . ?
C111 C112 C113 C114 -0.9(7) . . . . ?
C12 C11 C114 C113 177.5(4) . . . . ?
C115 C11 C114 C113 -6.8(6) . . . . ?
C12 C11 C114 C19 -0.4(6) . . . . ?
C115 C11 C114 C19 175.3(4) . . . . ?
C112 C113 C114 C11 -179.3(4) . . . . ?
C112 C113 C114 C19 -1.4(6) . . . . ?
C18 C19 C114 C11 -0.4(6) . . . . ?
C110 C19 C114 C11 -178.4(4) . . . . ?
C18 C19 C114 C113 -178.4(4) . . . . ?
C110 C19 C114 C113 3.6(6) . . . . ?
C12 C11 C115 O11 120.0(5) . . . . ?
C114 C11 C115 O11 -55.8(6) . . . . ?
C12 C11 C115 O12 -60.1(5) . . . . ?
C114 C11 C115 O12 124.1(4) . . . . ?
N21 C21 C22 C23 -2.7(6) . . . . ?
N22 C21 C22 C23 178.8(4) . . . . ?
N21 C21 C22 Br1 174.5(3) . . . . ?
N22 C21 C22 Br1 -3.9(6) . . . . ?
C21 C22 C23 C24 1.6(6) . . . . ?
Br1 C22 C23 C24 -175.6(3) . . . . ?
C22 C23 C24 C25 0.4(6) . . . . ?
C23 C24 C25 N21 -1.4(6) . . . . ?
N22 C21 N21 C25 -179.7(4) . . . . ?
C22 C21 N21 C25 1.8(6) . . . . ?
C24 C25 N21 C21 0.2(6) . . . . ?

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
O12 H12 N21 0.97(7) 1.67(7) 2.628(4) 171(6) . yes
N22 H22A O11 0.81(5) 2.16(5) 2.941(6) 164(4) . yes
N22 H22B Br1 0.75(5) 2.70(5) 3.109(5) 116(4) . 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_8
_audit_block_doi                 10.5517/ccdc.csd.cc1j2tbr
_database_code_depnum_ccdc_archive 'CCDC 1402884'
loop_
_audit_author_name
_audit_author_address
'Professor Andreas Lemmerer'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2018-12-06 deposited with the CCDC.	2019-08-07 downloaded from the CCDC.
;

_audit_creation_date             2018-12-06T08:20:29-00:00
_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 H10 O2, C6 H3 N3 O6, C5 H5 Cl N2'
_chemical_formula_sum            'C26 H18 Cl N5 O8'
_chemical_formula_weight         563.9

#----------------------------------------------------------------------------#
#                   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                   8.9310(10)
_cell_length_b                   7.2239(8)
_cell_length_c                   38.218(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.402(2)
_cell_angle_gamma                90
_cell_volume                     2458.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.22
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.087
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_special_details           
;
 Absorption corrections were made using the program SADABS.
;

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

_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al.,2015)'
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_T_max  0.74

#----------------------------------------------------------------------------#
#                   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  0.029
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_number            27353
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4573
_reflns_number_gt                3645
_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-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
;
Ortep for Windows (Farrugia, 2012), Mercury (Macrae et al., 2006)'
;
_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)+(0.0465P)²+1.0599P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4573
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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 0.32509(18) 0.1320(2) 0.15184(5) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.41385(18) 0.1507(2) 0.18265(5) 0.0278(4) Uani 1 1 d . . . . .
H2 H 0.373249 0.188062 0.203797 0.033 Uiso 1 1 calc R U . . .
C3 C 0.56469(19) 0.1126(2) 0.18140(4) 0.0282(4) Uani 1 1 d . . . . .
C4 C 0.62847(19) 0.0604(2) 0.15129(5) 0.0288(4) Uani 1 1 d . . . . .
H4 H 0.732633 0.034018 0.151178 0.035 Uiso 1 1 calc R U . . .
C5 C 0.53279(19) 0.0485(2) 0.12125(4) 0.0283(4) Uani 1 1 d . . . . .
C6 C 0.38118(19) 0.0820(2) 0.12061(5) 0.0292(4) Uani 1 1 d . . . . .
H6 H 0.31786 0.071159 0.099578 0.035 Uiso 1 1 calc R U . . .
N1 N 0.16184(17) 0.1621(2) 0.15240(5) 0.0359(4) Uani 1 1 d . . . . .
N2 N 0.66227(18) 0.1267(2) 0.21410(4) 0.0424(4) Uani 1 1 d . . . . .
N3 N 0.5971(2) 0.0000(2) 0.08820(4) 0.0391(4) Uani 1 1 d . . . . .
O1 O 0.08108(14) 0.09956(19) 0.12797(4) 0.0474(4) Uani 1 1 d . . . . .
O2 O 0.11812(15) 0.2457(2) 0.17750(4) 0.0488(4) Uani 1 1 d . . . . .
O3 O 0.60709(18) 0.1830(3) 0.24015(4) 0.0684(5) Uani 1 1 d . . . . .
O4 O 0.79315(16) 0.0815(3) 0.21300(4) 0.0740(5) Uani 1 1 d . . . . .
O5 O 0.72678(18) -0.0551(2) 0.08959(4) 0.0574(4) Uani 1 1 d . . . . .
O6 O 0.51780(18) 0.0224(2) 0.06099(4) 0.0550(4) Uani 1 1 d . . . . .
C11 C 0.37946(16) 0.6025(2) 0.13483(4) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.33584(17) 0.6615(2) 0.16751(4) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.18625(19) 0.7197(2) 0.17271(5) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.110146 0.709183 0.154041 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1517(2) 0.7899(3) 0.20404(5) 0.0392(5) Uani 1 1 d . . . . .
H14 H 0.052021 0.829501 0.207004 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2629(3) 0.8045(3) 0.23231(5) 0.0440(5) Uani 1 1 d . . . . .
H15 H 0.237922 0.857517 0.253846 0.053 Uiso 1 1 calc R U . . .
C16 C 0.4044(2) 0.7438(3) 0.22903(5) 0.0402(5) Uani 1 1 d . . . . .
H16 H 0.476371 0.74961 0.248643 0.048 Uiso 1 1 calc R U . . .
C17 C 0.44712(19) 0.6711(2) 0.19657(4) 0.0291(4) Uani 1 1 d . . . . .
C18 C 0.5940(2) 0.6172(2) 0.19188(5) 0.0343(4) Uani 1 1 d . . . . .
H18 H 0.666718 0.620954 0.211356 0.041 Uiso 1 1 calc R U . . .
C19 C 0.63731(18) 0.5582(2) 0.15960(5) 0.0311(4) Uani 1 1 d . . . . .
C110 C 0.78807(19) 0.5031(3) 0.15432(6) 0.0436(5) Uani 1 1 d . . . . .
H110 H 0.861831 0.504805 0.173601 0.052 Uiso 1 1 calc R U . . .
C111 C 0.8273(2) 0.4488(3) 0.12247(7) 0.0488(6) Uani 1 1 d . . . . .
H111 H 0.928086 0.413649 0.119556 0.059 Uiso 1 1 calc R U . . .
C112 C 0.7197(2) 0.4439(2) 0.09356(6) 0.0410(5) Uani 1 1 d . . . . .
H112 H 0.748914 0.405468 0.071303 0.049 Uiso 1 1 calc R U . . .
C113 C 0.57479(19) 0.4933(2) 0.09697(5) 0.0304(4) Uani 1 1 d . . . . .
H113 H 0.503966 0.488656 0.077131 0.036 Uiso 1 1 calc R U . . .
C114 C 0.52787(17) 0.5520(2) 0.13006(4) 0.0239(4) Uani 1 1 d . . . . .
C115 C 0.26534(16) 0.5943(2) 0.10382(4) 0.0224(3) Uani 1 1 d . . . . .
O11 O 0.17641(13) 0.46822(17) 0.09984(3) 0.0362(3) Uani 1 1 d . . . . .
O12 O 0.27426(14) 0.73282(17) 0.08243(3) 0.0371(3) Uani 1 1 d . . . . .
H12 H 0.206671 0.723405 0.065989 0.056 Uiso 1 1 calc R U . . .
C21 C 0.14661(18) 0.8063(2) -0.00140(4) 0.0245(4) Uani 1 1 d . . . . .
C22 C 0.05249(19) 0.8229(2) -0.03237(5) 0.0294(4) Uani 1 1 d . . . . .
H22 H 0.090571 0.869362 -0.053186 0.035 Uiso 1 1 calc R U . . .
C23 C -0.0942(2) 0.7716(2) -0.03219(5) 0.0326(4) Uani 1 1 d . . . . .
H23 H -0.159265 0.781038 -0.052979 0.039 Uiso 1 1 calc R U . . .
C24 C -0.14823(18) 0.7053(2) -0.00147(5) 0.0298(4) Uani 1 1 d . . . . .
C25 C -0.05223(18) 0.6910(2) 0.02797(5) 0.0281(4) Uani 1 1 d . . . . .
H25 H -0.088883 0.645602 0.04902 0.034 Uiso 1 1 calc R U . . .
N21 N 0.09331(14) 0.73984(18) 0.02784(4) 0.0250(3) Uani 1 1 d . . . . .
N22 N 0.29355(18) 0.8534(2) 0.00016(6) 0.0362(4) Uani 1 1 d . . . . .
Cl21 Cl -0.33541(5) 0.64336(7) -0.00035(2) 0.04921(17) Uani 1 1 d . . . . .
H22A H 0.345(3) 0.855(3) 0.0206(7) 0.056(7) Uiso 1 1 d . . . . .
H22B H 0.328(2) 0.904(3) -0.0171(6) 0.048(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 C2 1.375(2) . ?
C1 C6 1.378(2) . ?
C1 N1 1.476(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.95 . ?
C3 C4 1.375(2) . ?
C3 N2 1.471(2) . ?
C4 C5 1.380(2) . ?
C4 H4 0.95 . ?
C5 C6 1.374(2) . ?
C5 N3 1.470(2) . ?
C6 H6 0.95 . ?
N1 O1 1.222(2) . ?
N1 O2 1.223(2) . ?
N2 O3 1.215(2) . ?
N2 O4 1.217(2) . ?
N3 O5 1.222(2) . ?
N3 O6 1.223(2) . ?
C11 C114 1.400(2) . ?
C11 C12 1.403(2) . ?
C11 C115 1.504(2) . ?
C12 C13 1.429(2) . ?
C12 C17 1.434(2) . ?
C13 C14 1.357(3) . ?
C13 H13 0.95 . ?
C14 C15 1.414(3) . ?
C14 H14 0.95 . ?
C15 C16 1.353(3) . ?
C15 H15 0.95 . ?
C16 C17 1.426(3) . ?
C16 H16 0.95 . ?
C17 C18 1.393(3) . ?
C18 C19 1.388(3) . ?
C18 H18 0.95 . ?
C19 C110 1.433(2) . ?
C19 C114 1.436(2) . ?
C110 C111 1.351(3) . ?
C110 H110 0.95 . ?
C111 C112 1.408(3) . ?
C111 H111 0.95 . ?
C112 C113 1.358(2) . ?
C112 H112 0.95 . ?
C113 C114 1.427(2) . ?
C113 H113 0.95 . ?
C115 O11 1.2106(19) . ?
C115 O12 1.2980(19) . ?
O12 H12 0.84 . ?
C21 N21 1.337(2) . ?
C21 N22 1.353(2) . ?
C21 C22 1.403(2) . ?
C22 C23 1.363(2) . ?
C22 H22 0.95 . ?
C23 C24 1.388(3) . ?
C23 H23 0.95 . ?
C24 C25 1.365(2) . ?
C24 Cl21 1.7343(17) . ?
C25 N21 1.347(2) . ?
C25 H25 0.95 . ?
N22 H22A 0.88(2) . ?
N22 H22B 0.83(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.93(16) . . ?
C2 C1 N1 118.58(16) . . ?
C6 C1 N1 118.46(15) . . ?
C1 C2 C3 116.82(16) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 123.52(16) . . ?
C4 C3 N2 118.25(15) . . ?
C2 C3 N2 118.23(16) . . ?
C3 C4 C5 116.31(16) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C6 C5 C4 123.38(16) . . ?
C6 C5 N3 118.46(16) . . ?
C4 C5 N3 118.16(16) . . ?
C5 C6 C1 117.02(16) . . ?
C5 C6 H6 121.5 . . ?
C1 C6 H6 121.5 . . ?
O1 N1 O2 125.23(16) . . ?
O1 N1 C1 117.41(16) . . ?
O2 N1 C1 117.36(15) . . ?
O3 N2 O4 124.69(17) . . ?
O3 N2 C3 117.94(16) . . ?
O4 N2 C3 117.37(17) . . ?
O5 N3 O6 124.43(17) . . ?
O5 N3 C5 118.16(16) . . ?
O6 N3 C5 117.38(17) . . ?
C114 C11 C12 121.70(14) . . ?
C114 C11 C115 118.57(14) . . ?
C12 C11 C115 119.73(13) . . ?
C11 C12 C13 122.67(15) . . ?
C11 C12 C17 118.75(14) . . ?
C13 C12 C17 118.52(15) . . ?
C14 C13 C12 120.73(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.51(18) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.78(18) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.93(18) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 122.17(16) . . ?
C18 C17 C12 119.34(16) . . ?
C16 C17 C12 118.43(16) . . ?
C19 C18 C17 121.99(16) . . ?
C19 C18 H18 119 . . ?
C17 C18 H18 119 . . ?
C18 C19 C110 122.63(17) . . ?
C18 C19 C114 119.27(15) . . ?
C110 C19 C114 118.10(18) . . ?
C111 C110 C19 121.26(18) . . ?
C111 C110 H110 119.4 . . ?
C19 C110 H110 119.4 . . ?
C110 C111 C112 120.40(17) . . ?
C110 C111 H111 119.8 . . ?
C112 C111 H111 119.8 . . ?
C113 C112 C111 121.1(2) . . ?
C113 C112 H112 119.5 . . ?
C111 C112 H112 119.5 . . ?
C112 C113 C114 120.67(18) . . ?
C112 C113 H113 119.7 . . ?
C114 C113 H113 119.7 . . ?
C11 C114 C113 122.56(15) . . ?
C11 C114 C19 118.92(15) . . ?
C113 C114 C19 118.52(15) . . ?
O11 C115 O12 124.91(15) . . ?
O11 C115 C11 121.80(14) . . ?
O12 C115 C11 113.29(13) . . ?
C115 O12 H12 109.5 . . ?
N21 C21 N22 117.38(16) . . ?
N21 C21 C22 120.47(15) . . ?
N22 C21 C22 122.14(17) . . ?
C23 C22 C21 119.11(17) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 119.67(16) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 119.09(16) . . ?
C25 C24 Cl21 120.38(15) . . ?
C23 C24 Cl21 120.53(13) . . ?
N21 C25 C24 121.49(16) . . ?
N21 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C21 N21 C25 120.17(14) . . ?
C21 N22 H22A 119.0(15) . . ?
C21 N22 H22B 119.5(15) . . ?
H22A N22 H22B 120(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 -1.5(2) . . . . ?
N1 C1 C2 C3 176.90(14) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C1 C2 C3 N2 -178.50(15) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
N2 C3 C4 C5 179.85(15) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C3 C4 C5 N3 177.78(14) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
N3 C5 C6 C1 -178.31(14) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
N1 C1 C6 C5 -177.70(14) . . . . ?
C2 C1 N1 O1 -161.31(15) . . . . ?
C6 C1 N1 O1 17.1(2) . . . . ?
C2 C1 N1 O2 17.8(2) . . . . ?
C6 C1 N1 O2 -163.74(15) . . . . ?
C4 C3 N2 O3 175.86(18) . . . . ?
C2 C3 N2 O3 -4.7(3) . . . . ?
C4 C3 N2 O4 -3.8(3) . . . . ?
C2 C3 N2 O4 175.55(18) . . . . ?
C6 C5 N3 O5 -169.77(16) . . . . ?
C4 C5 N3 O5 11.0(2) . . . . ?
C6 C5 N3 O6 12.1(2) . . . . ?
C4 C5 N3 O6 -167.06(16) . . . . ?
C114 C11 C12 C13 177.81(14) . . . . ?
C115 C11 C12 C13 -1.6(2) . . . . ?
C114 C11 C12 C17 0.5(2) . . . . ?
C115 C11 C12 C17 -178.96(14) . . . . ?
C11 C12 C13 C14 -174.61(15) . . . . ?
C17 C12 C13 C14 2.7(2) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 -2.0(3) . . . . ?
C14 C15 C16 C17 2.8(3) . . . . ?
C15 C16 C17 C18 176.36(17) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C11 C12 C17 C18 -1.7(2) . . . . ?
C13 C12 C17 C18 -179.18(15) . . . . ?
C11 C12 C17 C16 175.55(15) . . . . ?
C13 C12 C17 C16 -1.9(2) . . . . ?
C16 C17 C18 C19 -175.63(16) . . . . ?
C12 C17 C18 C19 1.6(2) . . . . ?
C17 C18 C19 C110 179.71(16) . . . . ?
C17 C18 C19 C114 -0.1(2) . . . . ?
C18 C19 C110 C111 -179.05(17) . . . . ?
C114 C19 C110 C111 0.8(3) . . . . ?
C19 C110 C111 C112 -0.4(3) . . . . ?
C110 C111 C112 C113 0.0(3) . . . . ?
C111 C112 C113 C114 0.2(3) . . . . ?
C12 C11 C114 C113 -179.41(14) . . . . ?
C115 C11 C114 C113 0.0(2) . . . . ?
C12 C11 C114 C19 1.0(2) . . . . ?
C115 C11 C114 C19 -179.58(14) . . . . ?
C112 C113 C114 C11 -179.43(15) . . . . ?
C112 C113 C114 C19 0.2(2) . . . . ?
C18 C19 C114 C11 -1.2(2) . . . . ?
C110 C19 C114 C11 179.01(15) . . . . ?
C18 C19 C114 C113 179.19(15) . . . . ?
C110 C19 C114 C113 -0.6(2) . . . . ?
C114 C11 C115 O11 101.90(18) . . . . ?
C12 C11 C115 O11 -78.6(2) . . . . ?
C114 C11 C115 O12 -77.51(18) . . . . ?
C12 C11 C115 O12 101.95(17) . . . . ?
N21 C21 C22 C23 0.4(2) . . . . ?
N22 C21 C22 C23 179.49(15) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
C22 C23 C24 C25 -0.7(3) . . . . ?
C22 C23 C24 Cl21 178.72(13) . . . . ?
C23 C24 C25 N21 0.0(2) . . . . ?
Cl21 C24 C25 N21 -179.39(12) . . . . ?
N22 C21 N21 C25 179.80(14) . . . . ?
C22 C21 N21 C25 -1.1(2) . . . . ?
C24 C25 N21 C21 0.9(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
O12 H12 N21 0.84 1.71 2.5395(17) 167 . yes
N22 H22A O6 0.88(2) 2.42(2) 3.192(2) 147(2) 1_565 yes
N22 H22A O12 0.88(2) 2.64(2) 3.280(2) 130(2) . yes
N22 H22B O6 0.83(2) 2.31(2) 3.116(2) 162(2) 3_665 yes

