# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shrv593
_database_code_depnum_ccdc_archive 'CCDC 1818128'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 N8 O8, 0.5(C2 H3 N)'
_chemical_formula_sum            'C9 H5.50 N8.50 O8'
_chemical_formula_weight         360.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'y, x, -z'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'

_cell_length_a                   8.443(2)
_cell_length_b                   8.443(2)
_cell_length_c                   33.962(7)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                120.00(3)
_cell_volume                     2096.8(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8022
_cell_measurement_theta_min      3.034
_cell_measurement_theta_max      68.061

_exptl_crystal_description       plates
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             1098
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    1.349
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11485
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.905
_diffrn_reflns_theta_max         68.302
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2529
_reflns_number_gt                2190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.643
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+0.7943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 743 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2529
_refine_ls_number_parameters     242
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N27 N 0.0235(7) 0.0000 0.6667 0.0797(18) Uani 1 2 d S T P . .
O1 O -0.3732(4) 0.6481(5) 0.59826(10) 0.0799(10) Uani 1 1 d . . . . .
O2 O -0.4732(4) 0.6537(4) 0.54017(10) 0.0753(9) Uani 1 1 d . . . . .
N3 N -0.3575(4) 0.7124(4) 0.56572(10) 0.0499(8) Uani 1 1 d . . . . .
C4 C -0.1854(4) 0.8755(4) 0.55664(9) 0.0350(8) Uani 1 1 d . . . . .
C5 C -0.1589(5) 1.0314(5) 0.53726(10) 0.0363(8) Uani 1 1 d . . . . .
N6 N -0.2958(4) 1.0730(4) 0.52224(9) 0.0443(8) Uani 1 1 d . . . . .
O7 O -0.4395(4) 1.0042(4) 0.53992(9) 0.0632(8) Uani 1 1 d . . . . .
O8 O -0.2558(4) 1.1735(4) 0.49396(8) 0.0630(8) Uani 1 1 d . . . . .
N9 N 0.0158(4) 1.1598(4) 0.53523(8) 0.0376(6) Uani 1 1 d . . . . .
N10 N 0.1016(4) 1.0837(3) 0.55361(8) 0.0342(6) Uani 1 1 d . . . . .
C11 C 0.3013(4) 1.1785(5) 0.55823(10) 0.0400(8) Uani 1 1 d . . . . .
H11A H 0.3517 1.3098 0.5565 0.048 Uiso 1 1 calc R U . . .
H11B H 0.3554 1.1415 0.5376 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3427(5) 1.1281(4) 0.59805(11) 0.0404(8) Uani 1 1 d . . . . .
H12A H 0.4728 1.1729 0.6005 0.048 Uiso 1 1 calc R U . . .
H12B H 0.3066 1.1827 0.6188 0.048 Uiso 1 1 calc R U . . .
N13 N 0.2403(4) 0.9284(4) 0.60152(8) 0.0366(7) Uani 1 1 d . . . . .
N14 N 0.3063(4) 0.8346(4) 0.62088(8) 0.0401(7) Uani 1 1 d . . . . .
C15 C 0.1768(5) 0.6627(5) 0.61675(10) 0.0384(8) Uani 1 1 d . . . . .
N16 N 0.2116(5) 0.5231(4) 0.63303(10) 0.0520(8) Uani 1 1 d . . . . .
O17 O 0.2791(6) 0.5495(5) 0.66473(11) 0.1107(15) Uani 1 1 d . . . . .
O18 O 0.1761(5) 0.3939(5) 0.61246(10) 0.0815(10) Uani 1 1 d . . . . .
C19 C 0.0280(4) 0.6430(4) 0.59527(9) 0.0353(8) Uani 1 1 d . . . . .
N20 N -0.1287(4) 0.4798(4) 0.58159(9) 0.0435(7) Uani 1 1 d . . . . .
O21 O -0.1698(4) 0.3372(4) 0.59837(8) 0.0628(8) Uani 1 1 d . . . . .
O22 O -0.2100(4) 0.4921(4) 0.55319(9) 0.0703(9) Uani 1 1 d . . . . .
C23 C 0.0718(4) 0.8205(4) 0.58657(9) 0.0337(7) Uani 1 1 d . . . . .
C24 C -0.0113(4) 0.9127(4) 0.56672(9) 0.0327(7) Uani 1 1 d . . . . .
C25 C -0.2793(8) 0.0000 0.6667 0.080(2) Uani 1 2 d DS T P . .
H25A H -0.274(14) 0.08(3) 0.646(5) 0.121 Uiso 0.5 1 d D U P . .
H25B H -0.290(17) 0.05(3) 0.692(3) 0.121 Uiso 0.5 1 d D U P . .
H25C H -0.375(5) -0.122(7) 0.662(7) 0.121 Uiso 0.5 1 d D U P . .
C26 C -0.1110(7) 0.0000 0.6667 0.0524(13) Uani 1 2 d DS T P . .


_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
N27 C26 1.136(7) . ?
O1 N3 1.209(4) . ?
O2 N3 1.211(4) . ?
N3 C4 1.450(4) . ?
C4 C24 1.384(5) . ?
C4 C5 1.387(5) . ?
C5 N9 1.325(4) . ?
C5 N6 1.458(4) . ?
N6 O7 1.210(4) . ?
N6 O8 1.213(4) . ?
N9 N10 1.339(4) . ?
N10 C24 1.348(4) . ?
N10 C11 1.470(4) . ?
C11 C12 1.510(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N13 1.465(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N13 N14 1.346(4) . ?
N13 C23 1.347(4) . ?
N14 C15 1.317(4) . ?
C15 C19 1.389(5) . ?
C15 N16 1.458(4) . ?
N16 O17 1.186(4) . ?
N16 O18 1.201(4) . ?
C19 C23 1.384(5) . ?
C19 N20 1.429(4) . ?
N20 O21 1.215(4) . ?
N20 O22 1.218(4) . ?
C23 C24 1.449(4) . ?
C25 C26 1.421(9) . ?
C25 H25A 0.957(13) . ?
C25 H25B 0.957(14) . ?
C25 H25C 0.955(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 125.9(3) . . ?
O1 N3 C4 116.9(3) . . ?
O2 N3 C4 117.2(3) . . ?
C24 C4 C5 104.7(3) . . ?
C24 C4 N3 127.6(3) . . ?
C5 C4 N3 127.7(3) . . ?
N9 C5 C4 112.7(3) . . ?
N9 C5 N6 118.5(3) . . ?
C4 C5 N6 128.6(3) . . ?
O7 N6 O8 126.1(3) . . ?
O7 N6 C5 115.9(3) . . ?
O8 N6 C5 118.0(3) . . ?
C5 N9 N10 103.4(3) . . ?
N9 N10 C24 114.0(3) . . ?
N9 N10 C11 122.5(3) . . ?
C24 N10 C11 123.5(3) . . ?
N10 C11 C12 107.8(3) . . ?
N10 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
N10 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.5 . . ?
N13 C12 C11 108.0(3) . . ?
N13 C12 H12A 110.1 . . ?
C11 C12 H12A 110.1 . . ?
N13 C12 H12B 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N14 N13 C23 113.2(3) . . ?
N14 N13 C12 122.5(3) . . ?
C23 N13 C12 124.3(3) . . ?
C15 N14 N13 103.7(3) . . ?
N14 C15 C19 113.0(3) . . ?
N14 C15 N16 117.3(3) . . ?
C19 C15 N16 129.6(3) . . ?
O17 N16 O18 125.2(4) . . ?
O17 N16 C15 117.7(3) . . ?
O18 N16 C15 117.0(3) . . ?
C23 C19 C15 104.2(3) . . ?
C23 C19 N20 126.3(3) . . ?
C15 C19 N20 129.2(3) . . ?
O21 N20 O22 124.2(3) . . ?
O21 N20 C19 118.1(3) . . ?
O22 N20 C19 117.7(3) . . ?
N13 C23 C19 105.8(3) . . ?
N13 C23 C24 116.3(3) . . ?
C19 C23 C24 137.9(3) . . ?
N10 C24 C4 105.3(3) . . ?
N10 C24 C23 117.2(3) . . ?
C4 C24 C23 137.6(3) . . ?
C26 C25 H25A 108(2) . . ?
C26 C25 H25B 107(3) . . ?
H25A C25 H25B 110(3) . . ?
C26 C25 H25C 108(3) . . ?
H25A C25 H25C 110(3) . . ?
H25B C25 H25C 113(6) . . ?
N27 C26 C25 180.000(11) . . ?

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
O1 N3 C4 C24 40.7(5) . . . . ?
O2 N3 C4 C24 -139.9(4) . . . . ?
O1 N3 C4 C5 -136.6(4) . . . . ?
O2 N3 C4 C5 42.8(5) . . . . ?
C24 C4 C5 N9 -0.7(4) . . . . ?
N3 C4 C5 N9 177.1(3) . . . . ?
C24 C4 C5 N6 -175.9(3) . . . . ?
N3 C4 C5 N6 1.9(6) . . . . ?
N9 C5 N6 O7 -145.1(3) . . . . ?
C4 C5 N6 O7 29.8(5) . . . . ?
N9 C5 N6 O8 33.9(5) . . . . ?
C4 C5 N6 O8 -151.1(3) . . . . ?
C4 C5 N9 N10 0.1(4) . . . . ?
N6 C5 N9 N10 175.8(3) . . . . ?
C5 N9 N10 C24 0.7(3) . . . . ?
C5 N9 N10 C11 179.6(3) . . . . ?
N9 N10 C11 C12 143.5(3) . . . . ?
C24 N10 C11 C12 -37.7(4) . . . . ?
N10 C11 C12 N13 51.0(4) . . . . ?
C11 C12 N13 N14 145.3(3) . . . . ?
C11 C12 N13 C23 -35.8(4) . . . . ?
C23 N13 N14 C15 1.9(4) . . . . ?
C12 N13 N14 C15 -179.1(3) . . . . ?
N13 N14 C15 C19 -0.2(4) . . . . ?
N13 N14 C15 N16 176.8(3) . . . . ?
N14 C15 N16 O17 43.3(5) . . . . ?
C19 C15 N16 O17 -140.2(4) . . . . ?
N14 C15 N16 O18 -133.7(4) . . . . ?
C19 C15 N16 O18 42.8(6) . . . . ?
N14 C15 C19 C23 -1.4(4) . . . . ?
N16 C15 C19 C23 -178.0(3) . . . . ?
N14 C15 C19 N20 173.4(3) . . . . ?
N16 C15 C19 N20 -3.3(6) . . . . ?
C23 C19 N20 O21 -164.0(3) . . . . ?
C15 C19 N20 O21 22.4(5) . . . . ?
C23 C19 N20 O22 17.7(5) . . . . ?
C15 C19 N20 O22 -155.9(4) . . . . ?
N14 N13 C23 C19 -2.8(4) . . . . ?
C12 N13 C23 C19 178.2(3) . . . . ?
N14 N13 C23 C24 177.5(3) . . . . ?
C12 N13 C23 C24 -1.5(5) . . . . ?
C15 C19 C23 N13 2.4(4) . . . . ?
N20 C19 C23 N13 -172.6(3) . . . . ?
C15 C19 C23 C24 -178.0(4) . . . . ?
N20 C19 C23 C24 7.1(6) . . . . ?
N9 N10 C24 C4 -1.1(4) . . . . ?
C11 N10 C24 C4 180.0(3) . . . . ?
N9 N10 C24 C23 179.3(3) . . . . ?
C11 N10 C24 C23 0.4(4) . . . . ?
C5 C4 C24 N10 1.0(3) . . . . ?
N3 C4 C24 N10 -176.8(3) . . . . ?
C5 C4 C24 C23 -179.5(4) . . . . ?
N3 C4 C24 C23 2.7(6) . . . . ?
N13 C23 C24 N10 21.0(4) . . . . ?
C19 C23 C24 N10 -158.6(4) . . . . ?
N13 C23 C24 C4 -158.3(4) . . . . ?
C19 C23 C24 C4 22.0(7) . . . . ?

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
C11 H11A O2 0.97 2.58 3.530(5) 167.8 1_665
C11 H11B O7 0.97 2.52 3.250(4) 131.9 1_655
C12 H12A O21 0.97 2.62 3.577(5) 170.0 1_665
C12 H12B N27 0.97 2.66 3.309(5) 125.0 1_565
C12 H12B O18 0.97 2.53 3.226(5) 128.6 1_565
C25 H25A O21 0.957(13) 2.49(5) 3.422(3) 164(13) .

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_shrv594
_database_code_depnum_ccdc_archive 'CCDC 1818129'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 N8 O8'
_chemical_formula_sum            'C9 H6 N8 O8'
_chemical_formula_weight         354.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.4365(10)
_cell_length_b                   11.5612(12)
_cell_length_c                   12.9442(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.305(3)
_cell_angle_gamma                90
_cell_volume                     1411.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2356
_cell_measurement_theta_min      2.788
_cell_measurement_theta_max      24.326

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11903
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2574
_reflns_number_gt                1779
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
Nitro groups on carbon 16 and 20 display two-component disorder.  The 
ratio of major:minor components has been refined with a free variable
and refines to a final ratio of 78:22. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0540P)²+0.9288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     254
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3763(2) 0.42685(18) 0.45603(15) 0.0543(5) Uani 1 1 d . . . . .
O2 O 0.4704(3) 0.2833(2) 0.37866(17) 0.0814(8) Uani 1 1 d . . . . .
N3 N 0.4575(2) 0.3448(2) 0.45372(17) 0.0455(6) Uani 1 1 d . . . . .
C4 C 0.5418(3) 0.3192(2) 0.54544(18) 0.0362(6) Uani 1 1 d . . . . .
C5 C 0.6742(3) 0.2665(2) 0.55348(19) 0.0390(6) Uani 1 1 d . . . . .
N6 N 0.7674(3) 0.2353(2) 0.47155(18) 0.0509(6) Uani 1 1 d . . . . .
O7 O 0.7664(3) 0.2973(3) 0.39609(19) 0.0919(9) Uani 1 1 d . . . . .
O8 O 0.8411(2) 0.1510(2) 0.48286(16) 0.0706(7) Uani 1 1 d . . . . .
N9 N 0.7203(2) 0.2537(2) 0.65015(16) 0.0418(6) Uani 1 1 d . . . . .
N10 N 0.6165(2) 0.29921(19) 0.70526(15) 0.0374(5) Uani 1 1 d . . . . .
C11 C 0.6254(3) 0.2997(2) 0.81929(18) 0.0424(6) Uani 1 1 d . . . . .
H11A H 0.7043 0.2514 0.8430 0.051 Uiso 1 1 calc R U . . .
H11B H 0.5393 0.2663 0.8449 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6452(3) 0.4200(3) 0.8641(2) 0.0477(7) Uani 1 1 d . . . . .
H12A H 0.7454 0.4388 0.8660 0.057 Uiso 1 1 calc R U . . .
H12B H 0.6148 0.4196 0.9348 0.057 Uiso 1 1 calc R U . . .
C13 C 0.5645(3) 0.5142(2) 0.8046(2) 0.0479(7) Uani 1 1 d . . . . .
H13A H 0.5568 0.5816 0.8487 0.058 Uiso 1 1 calc R U . . .
H13B H 0.6179 0.5366 0.7453 0.058 Uiso 1 1 calc R U . . .
N14 N 0.4216(2) 0.47800(18) 0.76873(16) 0.0397(5) Uani 1 1 d . . . . .
N15 N 0.3052(3) 0.5242(2) 0.80865(19) 0.0520(6) Uani 1 1 d . . . . .
C16 C 0.1997(3) 0.4738(2) 0.7579(2) 0.0497(7) Uani 1 1 d . . . . .
N17 N 0.0562(3) 0.5085(3) 0.7837(3) 0.0794(9) Uani 1 1 d D U . . .
O18A O 0.0313(4) 0.5130(5) 0.8755(3) 0.1318(19) Uani 0.782(5) 1 d D U P A 1
O19A O -0.0265(4) 0.5294(4) 0.7142(4) 0.1102(15) Uani 0.782(5) 1 d D U P A 1
O18B O -0.0351(15) 0.4360(13) 0.7581(15) 0.129(5) Uani 0.218(5) 1 d D U P A 2
O19B O 0.0297(12) 0.6003(8) 0.8076(11) 0.085(4) Uani 0.218(5) 1 d D U P A 2
C20 C 0.2444(3) 0.3952(2) 0.6848(2) 0.0415(6) Uani 1 1 d . . . . .
N21 N 0.1623(2) 0.3183(2) 0.6203(2) 0.0608(7) Uani 1 1 d D . . . .
O22A O 0.0362(3) 0.3060(4) 0.6427(3) 0.0916(14) Uani 0.782(5) 1 d D U P A 1
O22B O 0.0604(14) 0.3674(13) 0.5689(12) 0.103(5) Uani 0.218(5) 1 d D U P A 2
O23 O 0.2213(2) 0.2573(2) 0.56054(18) 0.0637(6) Uani 1 1 d . . . . .
C24 C 0.3908(2) 0.3997(2) 0.69372(18) 0.0332(6) Uani 1 1 d . . . . .
C25 C 0.5066(2) 0.3403(2) 0.64576(18) 0.0336(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.220(3) . ?
O2 N3 1.214(3) . ?
N3 C4 1.433(3) . ?
C4 C25 1.375(3) . ?
C4 C5 1.390(4) . ?
C5 N9 1.316(3) . ?
C5 N6 1.451(3) . ?
N6 O8 1.202(3) . ?
N6 O7 1.211(3) . ?
N9 N10 1.342(3) . ?
N10 C25 1.353(3) . ?
N10 C11 1.475(3) . ?
C11 C12 1.516(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.521(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N14 1.469(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N14 N15 1.344(3) . ?
N14 C24 1.351(3) . ?
N15 C16 1.307(4) . ?
C16 C20 1.390(4) . ?
C16 N17 1.463(4) . ?
N17 O19B 1.137(7) . ?
N17 O19A 1.192(4) . ?
N17 O18A 1.222(5) . ?
N17 O18B 1.238(8) . ?
C20 C24 1.383(3) . ?
C20 N21 1.427(4) . ?
N21 O23 1.200(3) . ?
N21 O22A 1.245(3) . ?
N21 O22B 1.281(8) . ?
C24 C25 1.451(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
O2 N3 O1 123.9(2) . . ?
O2 N3 C4 118.1(2) . . ?
O1 N3 C4 118.0(2) . . ?
C25 C4 C5 104.9(2) . . ?
C25 C4 N3 126.7(2) . . ?
C5 C4 N3 128.3(2) . . ?
N9 C5 C4 112.5(2) . . ?
N9 C5 N6 118.7(2) . . ?
C4 C5 N6 128.6(2) . . ?
O8 N6 O7 124.3(2) . . ?
O8 N6 C5 118.5(2) . . ?
O7 N6 C5 117.2(2) . . ?
C5 N9 N10 103.95(19) . . ?
N9 N10 C25 113.22(19) . . ?
N9 N10 C11 121.34(19) . . ?
C25 N10 C11 125.4(2) . . ?
N10 C11 C12 112.8(2) . . ?
N10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 114.4(2) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N14 C13 C12 113.0(2) . . ?
N14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
N14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N15 N14 C24 112.8(2) . . ?
N15 N14 C13 121.3(2) . . ?
C24 N14 C13 125.9(2) . . ?
C16 N15 N14 104.3(2) . . ?
N15 C16 C20 112.8(2) . . ?
N15 C16 N17 117.1(3) . . ?
C20 C16 N17 130.0(3) . . ?
O19A N17 O18A 125.4(4) . . ?
O19B N17 O18B 123.2(10) . . ?
O19B N17 C16 122.3(7) . . ?
O19A N17 C16 117.9(4) . . ?
O18A N17 C16 116.7(4) . . ?
O18B N17 C16 113.2(9) . . ?
C24 C20 C16 104.4(2) . . ?
C24 C20 N21 126.1(2) . . ?
C16 C20 N21 129.3(2) . . ?
O23 N21 O22A 123.8(3) . . ?
O23 N21 O22B 106.5(8) . . ?
O23 N21 C20 119.2(2) . . ?
O22A N21 C20 115.9(3) . . ?
O22B N21 C20 114.0(7) . . ?
N14 C24 C20 105.7(2) . . ?
N14 C24 C25 118.8(2) . . ?
C20 C24 C25 135.5(2) . . ?
N10 C25 C4 105.4(2) . . ?
N10 C25 C24 119.7(2) . . ?
C4 C25 C24 134.7(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
O2 N3 C4 C25 -150.3(3) . . . . ?
O1 N3 C4 C25 29.2(4) . . . . ?
O2 N3 C4 C5 28.6(4) . . . . ?
O1 N3 C4 C5 -151.9(3) . . . . ?
C25 C4 C5 N9 0.5(3) . . . . ?
N3 C4 C5 N9 -178.6(2) . . . . ?
C25 C4 C5 N6 -173.7(3) . . . . ?
N3 C4 C5 N6 7.3(5) . . . . ?
N9 C5 N6 O8 38.5(4) . . . . ?
C4 C5 N6 O8 -147.6(3) . . . . ?
N9 C5 N6 O7 -140.8(3) . . . . ?
C4 C5 N6 O7 33.0(4) . . . . ?
C4 C5 N9 N10 -0.2(3) . . . . ?
N6 C5 N9 N10 174.6(2) . . . . ?
C5 N9 N10 C25 -0.1(3) . . . . ?
C5 N9 N10 C11 178.6(2) . . . . ?
N9 N10 C11 C12 110.9(3) . . . . ?
C25 N10 C11 C12 -70.6(3) . . . . ?
N10 C11 C12 C13 37.0(3) . . . . ?
C11 C12 C13 N14 40.2(3) . . . . ?
C12 C13 N14 N15 111.5(3) . . . . ?
C12 C13 N14 C24 -69.9(3) . . . . ?
C24 N14 N15 C16 0.1(3) . . . . ?
C13 N14 N15 C16 178.9(2) . . . . ?
N14 N15 C16 C20 -0.2(3) . . . . ?
N14 N15 C16 N17 -179.0(3) . . . . ?
N15 C16 N17 O19B 33.8(10) . . . . ?
C20 C16 N17 O19B -144.8(10) . . . . ?
N15 C16 N17 O19A 133.1(4) . . . . ?
C20 C16 N17 O19A -45.5(6) . . . . ?
N15 C16 N17 O18A -47.2(5) . . . . ?
C20 C16 N17 O18A 134.2(5) . . . . ?
N15 C16 N17 O18B -159.2(11) . . . . ?
C20 C16 N17 O18B 22.2(12) . . . . ?
N15 C16 C20 C24 0.2(3) . . . . ?
N17 C16 C20 C24 178.8(3) . . . . ?
N15 C16 C20 N21 175.1(3) . . . . ?
N17 C16 C20 N21 -6.2(5) . . . . ?
C24 C20 N21 O23 -6.9(5) . . . . ?
C16 C20 N21 O23 179.1(3) . . . . ?
C24 C20 N21 O22A 161.5(3) . . . . ?
C16 C20 N21 O22A -12.4(5) . . . . ?
C24 C20 N21 O22B -134.2(10) . . . . ?
C16 C20 N21 O22B 51.9(10) . . . . ?
N15 N14 C24 C20 0.0(3) . . . . ?
C13 N14 C24 C20 -178.8(2) . . . . ?
N15 N14 C24 C25 -178.2(2) . . . . ?
C13 N14 C24 C25 3.0(4) . . . . ?
C16 C20 C24 N14 -0.1(3) . . . . ?
N21 C20 C24 N14 -175.2(3) . . . . ?
C16 C20 C24 C25 177.7(3) . . . . ?
N21 C20 C24 C25 2.5(5) . . . . ?
N9 N10 C25 C4 0.4(3) . . . . ?
C11 N10 C25 C4 -178.3(2) . . . . ?
N9 N10 C25 C24 -175.6(2) . . . . ?
C11 N10 C25 C24 5.8(4) . . . . ?
C5 C4 C25 N10 -0.5(3) . . . . ?
N3 C4 C25 N10 178.6(2) . . . . ?
C5 C4 C25 C24 174.6(3) . . . . ?
N3 C4 C25 C24 -6.4(5) . . . . ?
N14 C24 C25 N10 43.8(3) . . . . ?
C20 C24 C25 N10 -133.8(3) . . . . ?
N14 C24 C25 C4 -130.7(3) . . . . ?
C20 C24 C25 C4 51.7(5) . . . . ?

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
C11 H11A O2 0.97 2.57 3.451(4) 151.6 4_666
C12 H12A O18B 0.97 2.54 3.369(15) 142.9 1_655
C13 H13A O8 0.97 2.48 3.266(4) 137.8 2_656
C13 H13B O1 0.97 2.64 3.509(3) 148.7 3_666

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_shrv597
_database_code_depnum_ccdc_archive 'CCDC 1818132'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 N8 O4'
_chemical_formula_sum            'C7 H6 N8 O4'
_chemical_formula_weight         266.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6012(4)
_cell_length_b                   11.5875(5)
_cell_length_c                   9.7940(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.837(2)
_cell_angle_gamma                90
_cell_volume                     1081.87(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2816
_cell_measurement_theta_min      2.735
_cell_measurement_theta_max      23.926

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12676
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         30.213
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3091
_reflns_number_gt                2082
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.1804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3091
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.76632(13) 0.63148(11) 0.45668(13) 0.0591(3) Uani 1 1 d . . . . .
O2 O 0.70081(14) 0.69617(10) 0.25178(13) 0.0592(3) Uani 1 1 d . . . . .
N3 N 0.70072(14) 0.62413(11) 0.34272(14) 0.0440(3) Uani 1 1 d . . . . .
C4 C 0.61415(15) 0.52210(13) 0.31406(14) 0.0369(3) Uani 1 1 d . . . . .
N5 N 0.53584(14) 0.51050(12) 0.19547(12) 0.0454(3) Uani 1 1 d . . . . .
N6 N 0.47538(13) 0.40702(12) 0.21168(11) 0.0411(3) Uani 1 1 d . . . . .
C7 C 0.3773(2) 0.35798(16) 0.09943(16) 0.0576(5) Uani 1 1 d . . . . .
H7A H 0.4002 0.3879 0.0123 0.069 Uiso 1 1 calc R U . . .
H7B H 0.2827 0.3826 0.1105 0.069 Uiso 1 1 calc R U . . .
C8 C 0.38196(18) 0.22827(16) 0.09605(16) 0.0539(4) Uani 1 1 d . . . . .
H8A H 0.3404 0.2026 0.0060 0.065 Uiso 1 1 calc R U . . .
H8B H 0.4794 0.2042 0.1071 0.065 Uiso 1 1 calc R U . . .
C9 C 0.30879(19) 0.16868(15) 0.20255(17) 0.0551(5) Uani 1 1 d . . . . .
H9A H 0.2150 0.2002 0.2006 0.066 Uiso 1 1 calc R U . . .
H9B H 0.2998 0.0873 0.1797 0.066 Uiso 1 1 calc R U . . .
N10 N 0.38223(13) 0.18047(11) 0.34259(12) 0.0396(3) Uani 1 1 d . . . . .
N11 N 0.35995(13) 0.10035(11) 0.43787(13) 0.0443(3) Uani 1 1 d . . . . .
C12 C 0.44276(15) 0.13836(12) 0.54495(14) 0.0386(3) Uani 1 1 d . . . . .
N13 N 0.45316(15) 0.07686(13) 0.67512(14) 0.0495(3) Uani 1 1 d . . . . .
O14 O 0.37681(14) -0.00657(12) 0.68141(14) 0.0690(4) Uani 1 1 d . . . . .
O15 O 0.53830(17) 0.11149(13) 0.76758(13) 0.0742(4) Uani 1 1 d . . . . .
N16 N 0.51613(12) 0.23373(11) 0.53029(11) 0.0383(3) Uani 1 1 d . . . . .
C17 C 0.47479(14) 0.25964(12) 0.39924(14) 0.0344(3) Uani 1 1 d . . . . .
C18 C 0.52062(14) 0.36504(12) 0.33759(13) 0.0337(3) Uani 1 1 d . . . . .
N19 N 0.61050(12) 0.43766(11) 0.40611(11) 0.0373(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2175(17) . ?
O2 N3 1.2207(17) . ?
N3 C4 1.4533(19) . ?
C4 N5 1.3132(18) . ?
C4 N19 1.3338(17) . ?
N5 N6 1.3498(18) . ?
N6 C18 1.3485(17) . ?
N6 C7 1.4738(19) . ?
C7 C8 1.504(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.494(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N10 1.4720(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N10 C17 1.3497(18) . ?
N10 N11 1.3514(17) . ?
N11 C12 1.3143(19) . ?
C12 N16 1.3275(18) . ?
C12 N13 1.4534(18) . ?
N13 O15 1.2137(19) . ?
N13 O14 1.2193(18) . ?
N16 C17 1.3318(17) . ?
C17 C18 1.4536(19) . ?
C18 N19 1.3287(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 125.16(14) . . ?
O1 N3 C4 117.10(13) . . ?
O2 N3 C4 117.74(13) . . ?
N5 C4 N19 117.68(13) . . ?
N5 C4 N3 120.54(13) . . ?
N19 C4 N3 121.78(12) . . ?
C4 N5 N6 101.29(11) . . ?
C18 N6 N5 109.38(12) . . ?
C18 N6 C7 130.60(13) . . ?
N5 N6 C7 120.02(11) . . ?
N6 C7 C8 112.55(13) . . ?
N6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 115.38(16) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
N10 C9 C8 113.24(13) . . ?
N10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C17 N10 N11 109.49(11) . . ?
C17 N10 C9 131.69(12) . . ?
N11 N10 C9 118.82(12) . . ?
C12 N11 N10 100.97(12) . . ?
N11 C12 N16 118.10(12) . . ?
N11 C12 N13 120.49(13) . . ?
N16 C12 N13 121.40(13) . . ?
O15 N13 O14 125.45(14) . . ?
O15 N13 C12 117.53(14) . . ?
O14 N13 C12 117.01(14) . . ?
C12 N16 C17 101.00(12) . . ?
N16 C17 N10 110.43(12) . . ?
N16 C17 C18 121.30(13) . . ?
N10 C17 C18 128.12(12) . . ?
N19 C18 N6 110.64(12) . . ?
N19 C18 C17 122.20(12) . . ?
N6 C18 C17 127.04(13) . . ?
C18 N19 C4 101.01(11) . . ?

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
O1 N3 C4 N5 177.11(14) . . . . ?
O2 N3 C4 N5 -2.0(2) . . . . ?
O1 N3 C4 N19 -2.6(2) . . . . ?
O2 N3 C4 N19 178.25(13) . . . . ?
N19 C4 N5 N6 -0.43(17) . . . . ?
N3 C4 N5 N6 179.85(12) . . . . ?
C4 N5 N6 C18 0.39(16) . . . . ?
C4 N5 N6 C7 -179.37(14) . . . . ?
C18 N6 C7 C8 -31.6(2) . . . . ?
N5 N6 C7 C8 148.09(15) . . . . ?
N6 C7 C8 C9 76.48(19) . . . . ?
C7 C8 C9 N10 -71.00(19) . . . . ?
C8 C9 N10 C17 23.2(3) . . . . ?
C8 C9 N10 N11 -156.02(15) . . . . ?
C17 N10 N11 C12 -0.34(15) . . . . ?
C9 N10 N11 C12 179.01(14) . . . . ?
N10 N11 C12 N16 0.00(17) . . . . ?
N10 N11 C12 N13 -179.85(13) . . . . ?
N11 C12 N13 O15 175.11(15) . . . . ?
N16 C12 N13 O15 -4.7(2) . . . . ?
N11 C12 N13 O14 -3.8(2) . . . . ?
N16 C12 N13 O14 176.39(14) . . . . ?
N11 C12 N16 C17 0.33(17) . . . . ?
N13 C12 N16 C17 -179.82(13) . . . . ?
C12 N16 C17 N10 -0.52(15) . . . . ?
C12 N16 C17 C18 175.35(13) . . . . ?
N11 N10 C17 N16 0.58(17) . . . . ?
C9 N10 C17 N16 -178.66(15) . . . . ?
N11 N10 C17 C18 -174.94(13) . . . . ?
C9 N10 C17 C18 5.8(3) . . . . ?
N5 N6 C18 N19 -0.26(17) . . . . ?
C7 N6 C18 N19 179.47(16) . . . . ?
N5 N6 C18 C17 175.90(13) . . . . ?
C7 N6 C18 C17 -4.4(3) . . . . ?
N16 C17 C18 N19 3.2(2) . . . . ?
N10 C17 C18 N19 178.30(14) . . . . ?
N16 C17 C18 N6 -172.54(14) . . . . ?
N10 C17 C18 N6 2.5(2) . . . . ?
N6 C18 N19 C4 0.00(15) . . . . ?
C17 C18 N19 C4 -176.38(13) . . . . ?
N5 C4 N19 C18 0.28(17) . . . . ?
N3 C4 N19 C18 180.00(13) . . . . ?

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
C9 H9A N16 0.97 2.50 3.300(2) 139.6 4_565
C7 H7A N5 0.97 2.49 3.455(2) 172.4 3_665

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_shrv596
_database_code_depnum_ccdc_archive 'CCDC 1818130'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N8 O4'
_chemical_formula_sum            'C6 H4 N8 O4'
_chemical_formula_weight         252.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.326(5)
_cell_length_b                   6.678(3)
_cell_length_c                   12.126(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.517(11)
_cell_angle_gamma                90
_cell_volume                     966.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1506
_cell_measurement_theta_min      3.415
_cell_measurement_theta_max      24.623

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5479
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.415
_diffrn_reflns_theta_max         29.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1376
_reflns_number_gt                903
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
Ethylene bridge displays two-component disorder with 77:23 ratio between
major:minor components.  Bonds to minor component have been restrained to 
the equivalent bond lengths in the major component.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+0.3224P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1376
_refine_ls_number_parameters     92
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67125(15) 0.6625(2) 0.57926(14) 0.0728(5) Uani 1 1 d . . . . .
O2 O 0.71023(16) 0.3749(3) 0.66325(13) 0.0805(5) Uani 1 1 d . . . . .
N3 N 0.67042(13) 0.4813(3) 0.58037(13) 0.0549(4) Uani 1 1 d . . . . .
C4 C 0.61494(14) 0.3805(3) 0.47485(13) 0.0434(4) Uani 1 1 d . . . . .
N5 N 0.60473(14) 0.1836(2) 0.47173(12) 0.0557(5) Uani 1 1 d . . . . .
N6 N 0.54975(13) 0.15730(18) 0.36261(12) 0.0470(4) Uani 1 1 d D . . . .
C7A C 0.4983(6) -0.0337(5) 0.3120(3) 0.0540(12) Uani 0.766(16) 1 d . . P A 1
H7A H 0.4215 -0.0430 0.3181 0.065 Uiso 0.766(16) 1 calc R U P A 1
H7B H 0.5399 -0.1470 0.3515 0.065 Uiso 0.766(16) 1 calc R U P A 1
C7B C 0.550(2) -0.0334(17) 0.3013(14) 0.069(5) Uani 0.234(16) 1 d D . P A 2
H7C H 0.5457 -0.1453 0.3508 0.083 Uiso 0.234(16) 1 calc R U P A 2
H7D H 0.6190 -0.0458 0.2766 0.083 Uiso 0.234(16) 1 calc R U P A 2
C8 C 0.52995(14) 0.33456(19) 0.30915(14) 0.0378(4) Uani 1 1 d . . . . .
N9 N 0.57093(11) 0.48306(18) 0.37965(11) 0.0412(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.210(2) . ?
O2 N3 1.228(2) . ?
N3 C4 1.456(2) . ?
C4 N5 1.321(2) . ?
C4 N9 1.335(2) . ?
N5 N6 1.338(2) . ?
N6 C8 1.3423(19) . ?
N6 C7B 1.476(4) . ?
N6 C7A 1.487(3) . ?
C7A C7A 1.515(8) 2_655 ?
C7A H7A 0.9700 . ?
C7A H7B 0.9700 . ?
C7B C7B 1.52(3) 2_655 ?
C7B H7C 0.9700 . ?
C7B H7D 0.9700 . ?
C8 N9 1.3240(19) . ?
C8 C8 1.439(3) 2_655 ?

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
O1 N3 O2 125.79(18) . . ?
O1 N3 C4 117.13(16) . . ?
O2 N3 C4 117.06(18) . . ?
N5 C4 N9 118.09(15) . . ?
N5 C4 N3 120.39(16) . . ?
N9 C4 N3 121.50(16) . . ?
C4 N5 N6 100.35(13) . . ?
N5 N6 C8 110.34(13) . . ?
N5 N6 C7B 123.1(6) . . ?
C8 N6 C7B 122.7(8) . . ?
N5 N6 C7A 125.33(19) . . ?
C8 N6 C7A 123.4(2) . . ?
N6 C7A C7A 107.1(4) . 2_655 ?
N6 C7A H7A 110.3 . . ?
C7A C7A H7A 110.3 2_655 . ?
N6 C7A H7B 110.3 . . ?
C7A C7A H7B 110.3 2_655 . ?
H7A C7A H7B 108.5 . . ?
N6 C7B C7B 107.8(12) . 2_655 ?
N6 C7B H7C 110.1 . . ?
C7B C7B H7C 110.1 2_655 . ?
N6 C7B H7D 110.1 . . ?
C7B C7B H7D 110.1 2_655 . ?
H7C C7B H7D 108.5 . . ?
N9 C8 N6 110.79(15) . . ?
N9 C8 C8 131.36(9) . 2_655 ?
N6 C8 C8 117.84(10) . 2_655 ?
C8 N9 C4 100.41(13) . . ?

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
O1 N3 C4 N5 -175.79(17) . . . . ?
O2 N3 C4 N5 2.8(2) . . . . ?
O1 N3 C4 N9 2.7(2) . . . . ?
O2 N3 C4 N9 -178.73(16) . . . . ?
N9 C4 N5 N6 0.9(2) . . . . ?
N3 C4 N5 N6 179.46(15) . . . . ?
C4 N5 N6 C8 -0.7(2) . . . . ?
C4 N5 N6 C7B 157.8(13) . . . . ?
C4 N5 N6 C7A -169.8(4) . . . . ?
N5 N6 C7A C7A -150.4(4) . . . 2_655 ?
C8 N6 C7A C7A 41.9(8) . . . 2_655 ?
N5 N6 C7B C7B 159.8(16) . . . 2_655 ?
C8 N6 C7B C7B -44(3) . . . 2_655 ?
N5 N6 C8 N9 0.3(2) . . . . ?
C7B N6 C8 N9 -158.3(12) . . . . ?
C7A N6 C8 N9 169.7(4) . . . . ?
N5 N6 C8 C8 -179.28(18) . . . 2_655 ?
C7B N6 C8 C8 22.1(12) . . . 2_655 ?
C7A N6 C8 C8 -9.9(4) . . . 2_655 ?
N6 C8 N9 C4 0.23(17) . . . . ?
C8 C8 N9 C4 179.7(2) 2_655 . . . ?
N5 C4 N9 C8 -0.74(19) . . . . ?
N3 C4 N9 C8 -179.28(15) . . . . ?

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
C7A H7B N9 0.97 2.51 3.394(5) 151.4 1_545
C7B H7C N9 0.97 2.51 3.358(15) 145.3 1_545
C7B H7D O2 0.97 2.34 3.06(3) 130.4 7_656

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.041

