# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# 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_cd16632
_database_code_depnum_ccdc_archive 'CCDC 1554915'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.	2019-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 N8 O9'
_chemical_formula_weight         334.19

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.6484(13)
_cell_length_b                   16.154(3)
_cell_length_c                   11.156(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.283(4)
_cell_angle_gamma                90
_cell_volume                     1323.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1936
_cell_measurement_theta_min      4.564
_cell_measurement_theta_max      47.011

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6433
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7408
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.282
_diffrn_reflns_theta_max         25.494
_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             2459
_reflns_number_gt                1899
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.4794P] 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         2459
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
N1 N -0.1887(2) 0.61534(12) 0.24690(17) 0.0367(5) Uani 1 1 d . . . . .
N2 N 0.1649(2) 0.61716(10) 0.40004(15) 0.0314(4) Uani 1 1 d . . . . .
N3 N -0.1510(3) 0.47898(15) 0.1788(2) 0.0567(6) Uani 1 1 d . . . . .
N4 N -0.2407(3) 0.75280(14) 0.3054(2) 0.0533(6) Uani 1 1 d . . . . .
N5 N 0.2183(2) 0.48759(11) 0.32124(16) 0.0352(4) Uani 1 1 d . . . . .
N6 N 0.2774(3) 0.44532(12) 0.43339(19) 0.0439(5) Uani 1 1 d . . . . .
N7 N 0.1334(3) 0.74604(11) 0.47416(18) 0.0418(5) Uani 1 1 d . . . . .
N8 N 0.0485(4) 0.77457(14) 0.5585(2) 0.0554(6) Uani 1 1 d . . . . .
O1 O -0.3454(2) 0.61349(12) 0.17218(18) 0.0594(5) Uani 1 1 d . . . . .
O2 O -0.1287(4) 0.47501(18) 0.0780(2) 0.1065(9) Uani 1 1 d . . . . .
O3 O -0.2252(4) 0.42885(16) 0.2253(3) 0.1080(10) Uani 1 1 d . . . . .
O4 O -0.3929(3) 0.74168(15) 0.3102(2) 0.0823(7) Uani 1 1 d . . . . .
O5 O -0.1724(3) 0.81814(13) 0.2902(2) 0.0781(7) Uani 1 1 d . . . . .
O6 O 0.1776(3) 0.44774(12) 0.50001(19) 0.0668(6) Uani 1 1 d . . . . .
O7 O 0.4171(3) 0.40754(12) 0.45225(19) 0.0669(6) Uani 1 1 d . . . . .
O8 O 0.1356(3) 0.82234(14) 0.6360(2) 0.0838(7) Uani 1 1 d . . . . .
O9 O -0.1056(3) 0.75149(14) 0.5491(2) 0.0719(6) Uani 1 1 d . . . . .
C1 C -0.0743(3) 0.55039(14) 0.2550(2) 0.0354(5) Uani 1 1 d . . . . .
C2 C 0.0999(3) 0.55330(12) 0.32759(18) 0.0297(5) Uani 1 1 d . . . . .
C3 C 0.0543(3) 0.67952(12) 0.39782(19) 0.0313(5) Uani 1 1 d . . . . .
C4 C -0.1208(3) 0.68136(13) 0.3202(2) 0.0347(5) Uani 1 1 d . . . . .
C5 C 0.3537(3) 0.50245(17) 0.2548(3) 0.0520(7) Uani 1 1 d . . . . .
H5A H 0.4415 0.5418 0.3003 0.078 Uiso 1 1 calc R U . . .
H5B H 0.2950 0.5239 0.1732 0.078 Uiso 1 1 calc R U . . .
H5C H 0.4139 0.4514 0.2471 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3259(3) 0.76376(17) 0.4976(3) 0.0577(7) Uani 1 1 d . . . . .
H6A H 0.3458 0.8223 0.5092 0.087 Uiso 1 1 calc R U . . .
H6B H 0.3661 0.7457 0.4277 0.087 Uiso 1 1 calc R U . . .
H6C H 0.3933 0.7350 0.5715 0.087 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.253(2) . ?
N1 C1 1.353(3) . ?
N1 C4 1.356(3) . ?
N2 C3 1.311(3) . ?
N2 C2 1.319(3) . ?
N3 O2 1.185(3) . ?
N3 O3 1.188(3) . ?
N3 C1 1.455(3) . ?
N4 O4 1.194(3) . ?
N4 O5 1.210(3) . ?
N4 C4 1.454(3) . ?
N5 N6 1.385(3) . ?
N5 C2 1.410(3) . ?
N5 C5 1.453(3) . ?
N6 O7 1.197(2) . ?
N6 O6 1.206(3) . ?
N7 N8 1.364(3) . ?
N7 C3 1.399(3) . ?
N7 C6 1.450(3) . ?
N8 O8 1.210(3) . ?
N8 O9 1.213(3) . ?
C1 C2 1.352(3) . ?
C3 C4 1.376(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C1 120.37(19) . . ?
O1 N1 C4 123.60(19) . . ?
C1 N1 C4 115.98(18) . . ?
C3 N2 C2 117.31(18) . . ?
O2 N3 O3 126.2(3) . . ?
O2 N3 C1 117.1(2) . . ?
O3 N3 C1 116.7(2) . . ?
O4 N4 O5 127.0(2) . . ?
O4 N4 C4 117.9(2) . . ?
O5 N4 C4 115.1(2) . . ?
N6 N5 C2 112.18(16) . . ?
N6 N5 C5 116.31(19) . . ?
C2 N5 C5 117.45(17) . . ?
O7 N6 O6 126.6(2) . . ?
O7 N6 N5 117.4(2) . . ?
O6 N6 N5 115.95(19) . . ?
N8 N7 C3 118.10(19) . . ?
N8 N7 C6 117.7(2) . . ?
C3 N7 C6 120.37(18) . . ?
O8 N8 O9 125.8(2) . . ?
O8 N8 N7 115.8(2) . . ?
O9 N8 N7 118.4(2) . . ?
C2 C1 N1 121.6(2) . . ?
C2 C1 N3 123.1(2) . . ?
N1 C1 N3 115.35(19) . . ?
N2 C2 C1 122.24(19) . . ?
N2 C2 N5 118.85(18) . . ?
C1 C2 N5 118.85(19) . . ?
N2 C3 C4 122.50(19) . . ?
N2 C3 N7 114.33(18) . . ?
C4 C3 N7 123.02(19) . . ?
N1 C4 C3 120.23(19) . . ?
N1 C4 N4 115.6(2) . . ?
C3 C4 N4 124.1(2) . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N7 C6 H6A 109.5 . . ?
N7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N5 N6 O7 -156.8(2) . . . . ?
C5 N5 N6 O7 -17.6(3) . . . . ?
C2 N5 N6 O6 26.2(3) . . . . ?
C5 N5 N6 O6 165.4(2) . . . . ?
C3 N7 N8 O8 168.2(2) . . . . ?
C6 N7 N8 O8 10.3(3) . . . . ?
C3 N7 N8 O9 -12.8(3) . . . . ?
C6 N7 N8 O9 -170.7(2) . . . . ?
O1 N1 C1 C2 174.8(2) . . . . ?
C4 N1 C1 C2 -3.0(3) . . . . ?
O1 N1 C1 N3 -4.0(3) . . . . ?
C4 N1 C1 N3 178.12(19) . . . . ?
O2 N3 C1 C2 -85.5(3) . . . . ?
O3 N3 C1 C2 92.1(3) . . . . ?
O2 N3 C1 N1 93.3(3) . . . . ?
O3 N3 C1 N1 -89.0(3) . . . . ?
C3 N2 C2 C1 -1.2(3) . . . . ?
C3 N2 C2 N5 175.79(17) . . . . ?
N1 C1 C2 N2 4.1(3) . . . . ?
N3 C1 C2 N2 -177.1(2) . . . . ?
N1 C1 C2 N5 -172.83(18) . . . . ?
N3 C1 C2 N5 5.9(3) . . . . ?
N6 N5 C2 N2 66.6(2) . . . . ?
C5 N5 C2 N2 -72.1(3) . . . . ?
N6 N5 C2 C1 -116.3(2) . . . . ?
C5 N5 C2 C1 105.0(2) . . . . ?
C2 N2 C3 C4 -2.6(3) . . . . ?
C2 N2 C3 N7 -178.33(17) . . . . ?
N8 N7 C3 N2 -126.8(2) . . . . ?
C6 N7 C3 N2 30.5(3) . . . . ?
N8 N7 C3 C4 57.5(3) . . . . ?
C6 N7 C3 C4 -145.1(2) . . . . ?
O1 N1 C4 C3 -178.42(19) . . . . ?
C1 N1 C4 C3 -0.7(3) . . . . ?
O1 N1 C4 N4 -1.3(3) . . . . ?
C1 N1 C4 N4 176.42(18) . . . . ?
N2 C3 C4 N1 3.6(3) . . . . ?
N7 C3 C4 N1 178.93(19) . . . . ?
N2 C3 C4 N4 -173.2(2) . . . . ?
N7 C3 C4 N4 2.1(3) . . . . ?
O4 N4 C4 N1 50.5(3) . . . . ?
O5 N4 C4 N1 -130.1(2) . . . . ?
O4 N4 C4 C3 -132.6(3) . . . . ?
O5 N4 C4 C3 46.9(3) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16604
_database_code_depnum_ccdc_archive 'CCDC 1554918'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.	2019-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N10 O14'
_chemical_formula_weight         468.24

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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.0912(5)
_cell_length_b                   7.0912(5)
_cell_length_c                   34.097(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1714.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2743
_cell_measurement_theta_min      4.779
_cell_measurement_theta_max      45.292

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9946
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1603
_reflns_number_gt                1478
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.3367P] 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_abs_structure_details 
; 
 Flack x determined using 494 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -1.2(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1603
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
N1 N 0.4950(3) 0.4950(3) 0.0000 0.0325(7) Uani 1 2 d S T P . .
N2 N 0.7682(3) 0.7682(3) 0.0000 0.0429(8) Uani 1 2 d S T P . .
N3 N 0.6347(4) 0.9340(4) 0.05229(9) 0.0567(7) Uani 1 1 d . . . . .
N4 N 0.3264(3) 0.6371(3) 0.04911(7) 0.0408(6) Uani 1 1 d . . . . .
N5 N 0.2218(4) 0.8002(4) 0.05442(8) 0.0488(6) Uani 1 1 d . . . . .
N6 N -0.1530(3) 0.4015(4) 0.09007(7) 0.0457(6) Uani 1 1 d . . . . .
O1 O 0.6848(5) 1.0848(4) 0.03959(9) 0.0876(10) Uani 1 1 d . . . . .
O2 O 0.5935(5) 0.8988(4) 0.08573(7) 0.0809(9) Uani 1 1 d . . . . .
O3 O 0.2695(4) 0.9360(3) 0.03519(7) 0.0648(7) Uani 1 1 d . . . . .
O4 O 0.0925(4) 0.7921(3) 0.07727(7) 0.0664(7) Uani 1 1 d . . . . .
O5 O -0.0689(3) 0.4382(3) 0.05405(6) 0.0432(5) Uani 1 1 d . . . . .
O6 O -0.0753(4) 0.3004(4) 0.11217(8) 0.0765(8) Uani 1 1 d . . . . .
O7 O -0.3006(4) 0.4812(4) 0.09356(8) 0.0771(8) Uani 1 1 d . . . . .
C1 C 0.4829(4) 0.6410(4) 0.02424(7) 0.0327(6) Uani 1 1 d . . . . .
C2 C 0.6255(4) 0.7749(4) 0.02421(8) 0.0380(6) Uani 1 1 d . . . . .
C3 C 0.2691(4) 0.4652(4) 0.06940(8) 0.0375(6) Uani 1 1 d . . . . .
H3A H 0.2279 0.4986 0.0956 0.045 Uiso 1 1 calc R U . . .
H3B H 0.3785 0.3841 0.0720 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1151(4) 0.3552(4) 0.04998(10) 0.0493(7) Uani 1 1 d . . . . .
H4A H 0.1441 0.3434 0.0223 0.059 Uiso 1 1 calc R U . . .
H4B H 0.1125 0.2292 0.0611 0.059 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.327(3) . ?
N1 C1 1.328(3) 7 ?
N2 C2 1.307(3) . ?
N2 C2 1.307(3) 7 ?
N3 O2 1.203(4) . ?
N3 O1 1.207(4) . ?
N3 C2 1.481(4) . ?
N4 N5 1.385(3) . ?
N4 C1 1.397(3) . ?
N4 C3 1.460(3) . ?
N5 O4 1.204(3) . ?
N5 O3 1.214(3) . ?
N6 O6 1.177(3) . ?
N6 O7 1.195(4) . ?
N6 O5 1.390(3) . ?
O5 C4 1.438(4) . ?
C1 C2 1.387(4) . ?
C3 C4 1.496(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

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
C1 N1 C1 119.2(3) . 7 ?
C2 N2 C2 117.1(3) . 7 ?
O2 N3 O1 126.5(3) . . ?
O2 N3 C2 116.4(3) . . ?
O1 N3 C2 117.1(3) . . ?
N5 N4 C1 119.2(2) . . ?
N5 N4 C3 119.1(2) . . ?
C1 N4 C3 121.7(2) . . ?
O4 N5 O3 126.8(3) . . ?
O4 N5 N4 116.9(3) . . ?
O3 N5 N4 116.3(2) . . ?
O6 N6 O7 129.3(3) . . ?
O6 N6 O5 118.6(3) . . ?
O7 N6 O5 112.0(3) . . ?
N6 O5 C4 113.5(2) . . ?
N1 C1 C2 119.1(3) . . ?
N1 C1 N4 114.5(2) . . ?
C2 C1 N4 126.4(2) . . ?
N2 C2 C1 122.7(3) . . ?
N2 C2 N3 113.7(3) . . ?
C1 C2 N3 123.6(3) . . ?
N4 C3 C4 115.4(2) . . ?
N4 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
N4 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
O5 C4 C3 114.0(2) . . ?
O5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
O5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?

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
C1 N4 N5 O4 -177.2(3) . . . . ?
C3 N4 N5 O4 3.3(4) . . . . ?
C1 N4 N5 O3 3.4(4) . . . . ?
C3 N4 N5 O3 -176.0(3) . . . . ?
O6 N6 O5 C4 -4.6(4) . . . . ?
O7 N6 O5 C4 175.8(3) . . . . ?
C1 N1 C1 C2 -1.45(17) 7 . . . ?
C1 N1 C1 N4 -178.5(2) 7 . . . ?
N5 N4 C1 N1 -135.3(2) . . . . ?
C3 N4 C1 N1 44.2(3) . . . . ?
N5 N4 C1 C2 48.0(4) . . . . ?
C3 N4 C1 C2 -132.6(3) . . . . ?
C2 N2 C2 C1 -1.54(19) 7 . . . ?
C2 N2 C2 N3 176.3(3) 7 . . . ?
N1 C1 C2 N2 3.1(4) . . . . ?
N4 C1 C2 N2 179.7(2) . . . . ?
N1 C1 C2 N3 -174.5(2) . . . . ?
N4 C1 C2 N3 2.1(4) . . . . ?
O2 N3 C2 N2 -137.1(3) . . . . ?
O1 N3 C2 N2 42.0(4) . . . . ?
O2 N3 C2 C1 40.8(4) . . . . ?
O1 N3 C2 C1 -140.1(3) . . . . ?
N5 N4 C3 C4 82.3(3) . . . . ?
C1 N4 C3 C4 -97.2(3) . . . . ?
N6 O5 C4 C3 -80.2(3) . . . . ?
N4 C3 C4 O5 -74.7(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
C4 H4B O3 0.97 2.52 3.207(4) 128.0 1_545
C4 H4A O3 0.97 2.51 3.227(4) 130.8 7_455
C3 H3B O7 0.97 2.49 3.163(4) 126.5 1_655
C3 H3B O6 0.97 2.62 3.195(4) 118.4 6
C3 H3A O2 0.97 2.63 3.598(4) 175.6 6_465

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16381
_database_code_depnum_ccdc_archive 'CCDC 1554917'
_audit_update_record             
;
2017-06-08 deposited with the CCDC.	2019-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 N8 O8'
_chemical_formula_weight         318.19

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   11.0661(15)
_cell_length_b                   13.9316(19)
_cell_length_c                   15.839(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2441.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2295
_cell_measurement_theta_min      5.144
_cell_measurement_theta_max      43.944

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6254
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13736
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2401
_reflns_number_gt                1970
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.6486P] 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     SHELXL
_refine_ls_extinction_coef       0.0054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2401
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
N1 N 0.29307(13) 0.14394(11) 0.59460(9) 0.0286(4) Uani 1 1 d . . . . .
N2 N 0.21912(13) 0.32718(11) 0.62628(10) 0.0331(4) Uani 1 1 d . . . . .
N3 N 0.42543(13) 0.14271(12) 0.70501(10) 0.0340(4) Uani 1 1 d . . . . .
N4 N 0.52448(14) 0.19190(14) 0.73533(11) 0.0407(4) Uani 1 1 d . . . . .
N5 N 0.16138(14) 0.12453(12) 0.48404(10) 0.0367(4) Uani 1 1 d . . . . .
N6 N 0.03795(16) 0.12484(13) 0.47012(11) 0.0406(4) Uani 1 1 d . . . . .
N7 N 0.31607(15) 0.33410(15) 0.75700(12) 0.0429(4) Uani 1 1 d . . . . .
N8 N 0.10819(16) 0.33838(13) 0.50160(13) 0.0465(5) Uani 1 1 d . . . . .
O1 O 0.59498(15) 0.14474(13) 0.77637(12) 0.0679(5) Uani 1 1 d . . . . .
O2 O 0.53454(13) 0.27645(11) 0.71884(10) 0.0480(4) Uani 1 1 d . . . . .
O3 O -0.00027(14) 0.06518(12) 0.42122(10) 0.0564(5) Uani 1 1 d . . . . .
O4 O -0.02252(13) 0.18411(13) 0.50672(12) 0.0595(5) Uani 1 1 d . . . . .
O5 O 0.32881(15) 0.28442(13) 0.81925(10) 0.0601(5) Uani 1 1 d . . . . .
O6 O 0.31709(16) 0.42082(13) 0.75487(11) 0.0640(5) Uani 1 1 d . . . . .
O7 O 0.12749(19) 0.32563(14) 0.42735(11) 0.0726(6) Uani 1 1 d . . . . .
O8 O 0.03926(17) 0.39625(13) 0.53045(13) 0.0708(6) Uani 1 1 d . . . . .
C1 C 0.33880(14) 0.19226(13) 0.65869(11) 0.0284(4) Uani 1 1 d . . . . .
C2 C 0.29312(15) 0.28295(13) 0.67694(12) 0.0309(4) Uani 1 1 d . . . . .
C3 C 0.18053(16) 0.28010(14) 0.56021(12) 0.0322(4) Uani 1 1 d . . . . .
C4 C 0.20939(16) 0.18435(14) 0.54668(11) 0.0292(4) Uani 1 1 d . . . . .
C5 C 0.4307(2) 0.03846(16) 0.70736(16) 0.0547(6) Uani 1 1 d . . . . .
H5A H 0.4904 0.0162 0.6680 0.082 Uiso 1 1 calc R U . . .
H5B H 0.3532 0.0125 0.6924 0.082 Uiso 1 1 calc R U . . .
H5C H 0.4520 0.0178 0.7632 0.082 Uiso 1 1 calc R U . . .
C6 C 0.2268(2) 0.03960(16) 0.45583(13) 0.0450(5) Uani 1 1 d . . . . .
H6A H 0.2004 -0.0152 0.4876 0.067 Uiso 1 1 calc R U . . .
H6B H 0.3119 0.0490 0.4644 0.067 Uiso 1 1 calc R U . . .
H6C H 0.2114 0.0291 0.3969 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.319(2) . ?
N1 C4 1.323(2) . ?
N2 C2 1.302(2) . ?
N2 C3 1.307(2) . ?
N3 N4 1.379(2) . ?
N3 C1 1.391(2) . ?
N3 C5 1.454(3) . ?
N4 O1 1.209(2) . ?
N4 O2 1.212(2) . ?
N5 N6 1.384(2) . ?
N5 C4 1.400(2) . ?
N5 C6 1.457(3) . ?
N6 O4 1.211(2) . ?
N6 O3 1.212(2) . ?
N7 O6 1.209(2) . ?
N7 O5 1.213(2) . ?
N7 C2 1.477(2) . ?
N8 O8 1.200(2) . ?
N8 O7 1.208(3) . ?
N8 C3 1.470(3) . ?
C1 C2 1.391(3) . ?
C3 C4 1.388(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 119.53(16) . . ?
C2 N2 C3 117.49(17) . . ?
N4 N3 C1 119.01(16) . . ?
N4 N3 C5 117.09(16) . . ?
C1 N3 C5 122.49(16) . . ?
O1 N4 O2 125.78(18) . . ?
O1 N4 N3 115.46(18) . . ?
O2 N4 N3 118.75(16) . . ?
N6 N5 C4 119.05(16) . . ?
N6 N5 C6 116.38(16) . . ?
C4 N5 C6 120.78(16) . . ?
O4 N6 O3 125.50(18) . . ?
O4 N6 N5 118.13(16) . . ?
O3 N6 N5 116.36(19) . . ?
O6 N7 O5 126.30(19) . . ?
O6 N7 C2 117.39(19) . . ?
O5 N7 C2 116.28(19) . . ?
O8 N8 O7 125.6(2) . . ?
O8 N8 C3 118.5(2) . . ?
O7 N8 C3 115.91(19) . . ?
N1 C1 N3 114.66(16) . . ?
N1 C1 C2 118.95(16) . . ?
N3 C1 C2 126.28(16) . . ?
N2 C2 C1 122.04(17) . . ?
N2 C2 N7 114.15(16) . . ?
C1 C2 N7 123.65(17) . . ?
N2 C3 C4 122.05(17) . . ?
N2 C3 N8 113.97(17) . . ?
C4 C3 N8 123.95(17) . . ?
N1 C4 C3 118.77(17) . . ?
N1 C4 N5 114.76(16) . . ?
C3 C4 N5 126.43(17) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N3 N4 O1 178.68(18) . . . . ?
C5 N3 N4 O1 -14.5(3) . . . . ?
C1 N3 N4 O2 -1.8(3) . . . . ?
C5 N3 N4 O2 164.97(19) . . . . ?
C4 N5 N6 O4 7.5(3) . . . . ?
C6 N5 N6 O4 165.73(19) . . . . ?
C4 N5 N6 O3 -172.97(17) . . . . ?
C6 N5 N6 O3 -14.7(3) . . . . ?
C4 N1 C1 N3 179.63(15) . . . . ?
C4 N1 C1 C2 3.3(2) . . . . ?
N4 N3 C1 N1 141.77(16) . . . . ?
C5 N3 C1 N1 -24.3(3) . . . . ?
N4 N3 C1 C2 -42.3(3) . . . . ?
C5 N3 C1 C2 151.7(2) . . . . ?
C3 N2 C2 C1 5.6(3) . . . . ?
C3 N2 C2 N7 -170.06(16) . . . . ?
N1 C1 C2 N2 -9.8(3) . . . . ?
N3 C1 C2 N2 174.37(16) . . . . ?
N1 C1 C2 N7 165.44(16) . . . . ?
N3 C1 C2 N7 -10.4(3) . . . . ?
O6 N7 C2 N2 -33.9(2) . . . . ?
O5 N7 C2 N2 144.17(18) . . . . ?
O6 N7 C2 C1 150.56(18) . . . . ?
O5 N7 C2 C1 -31.4(3) . . . . ?
C2 N2 C3 C4 4.5(3) . . . . ?
C2 N2 C3 N8 -173.69(16) . . . . ?
O8 N8 C3 N2 -38.6(3) . . . . ?
O7 N8 C3 N2 138.7(2) . . . . ?
O8 N8 C3 C4 143.2(2) . . . . ?
O7 N8 C3 C4 -39.5(3) . . . . ?
C1 N1 C4 C3 6.3(2) . . . . ?
C1 N1 C4 N5 -175.93(15) . . . . ?
N2 C3 C4 N1 -10.7(3) . . . . ?
N8 C3 C4 N1 167.33(17) . . . . ?
N2 C3 C4 N5 171.74(17) . . . . ?
N8 C3 C4 N5 -10.2(3) . . . . ?
N6 N5 C4 N1 136.98(17) . . . . ?
C6 N5 C4 N1 -20.3(2) . . . . ?
N6 N5 C4 C3 -45.4(3) . . . . ?
C6 N5 C4 C3 157.32(19) . . . . ?

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
C6 H6C O6 0.96 2.63 3.381(3) 135.4 7_565
C6 H6B O8 0.96 2.63 3.578(3) 169.0 4_556
C5 H5B O6 0.96 2.48 3.282(3) 140.7 8_655

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

