# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc1kktzx
_database_code_depnum_ccdc_archive 'CCDC 1447110'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 N8 O20'
_chemical_formula_sum            'C12 H6 N8 O20'
_chemical_formula_weight         582.25

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   12.9246(18)
_cell_length_b                   10.0302(15)
_cell_length_c                   8.6402(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.913(3)
_cell_angle_gamma                90.00
_cell_volume                     1071.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    862
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      23.72

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'TWINABS (Bruker, 2011)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'APEX2 CCD detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2076
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2076
_reflns_number_gt                1602
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.4888P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2076
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5146(2) 0.4026(2) 0.4002(3) 0.0200(6) Uani 1 1 d . . .
C2 C 0.41016(19) 0.4490(2) 0.3817(3) 0.0172(5) Uani 1 1 d . . .
C3 C 0.3962(2) 0.5487(2) 0.4838(3) 0.0193(5) Uani 1 1 d . . .
H3 H 0.3262 0.5833 0.4744 0.023 Uiso 1 1 calc R . .
C4 C 0.3122(2) 0.3880(2) 0.2656(3) 0.0203(6) Uani 1 1 d . . .
C5 C 0.1852(2) 0.4038(3) 0.0141(3) 0.0212(6) Uani 1 1 d . . .
H5A H 0.1235 0.3902 0.0585 0.025 Uiso 1 1 calc R . .
H5B H 0.2062 0.3165 -0.0211 0.025 Uiso 1 1 calc R . .
C6 C 0.1550(2) 0.5007(3) -0.1265(3) 0.0218(6) Uani 1 1 d . . .
N1 N 0.53193(19) 0.2972(2) 0.2913(3) 0.0299(6) Uani 1 1 d . . .
N2 N 0.04531(17) 0.4624(2) -0.2399(3) 0.0262(5) Uani 1 1 d . . .
N3 N 0.14590(18) 0.6432(2) -0.0695(3) 0.0257(5) Uani 1 1 d . . .
N4 N 0.2331(2) 0.5030(2) -0.2271(3) 0.0290(5) Uani 1 1 d . . .
O1 O 0.61894(16) 0.2410(2) 0.3268(3) 0.0463(6) Uani 1 1 d . . .
O2 O 0.45847(18) 0.2742(3) 0.1702(3) 0.0627(8) Uani 1 1 d . . .
O3 O 0.27468(14) 0.46274(17) 0.1335(2) 0.0239(4) Uani 1 1 d . . .
O4 O 0.26933(18) 0.2888(2) 0.2901(3) 0.0461(6) Uani 1 1 d . . .
O5 O 0.03608(16) 0.3447(2) -0.2732(2) 0.0360(5) Uani 1 1 d . . .
O6 O -0.02169(17) 0.5491(2) -0.2872(3) 0.0436(6) Uani 1 1 d . . .
O7 O 0.18836(15) 0.73044(19) -0.1259(3) 0.0356(5) Uani 1 1 d . . .
O8 O 0.09432(16) 0.6543(2) 0.0278(2) 0.0352(5) Uani 1 1 d . . .
O9 O 0.32856(16) 0.5041(2) -0.1530(2) 0.0389(5) Uani 1 1 d . . .
O10 O 0.19348(19) 0.5060(3) -0.3730(2) 0.0500(7) 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
C1 C3 1.378(3) 3_666 ?
C1 C2 1.392(3) . ?
C1 N1 1.476(3) . ?
C2 C3 1.379(3) . ?
C2 C4 1.498(3) . ?
C3 C1 1.378(3) 3_666 ?
C3 H3 0.9500 . ?
C4 O4 1.188(3) . ?
C4 O3 1.333(3) . ?
C5 O3 1.434(3) . ?
C5 C6 1.516(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N4 1.512(4) . ?
C6 N2 1.520(3) . ?
C6 N3 1.528(3) . ?
N1 O2 1.213(3) . ?
N1 O1 1.215(3) . ?
N2 O6 1.211(3) . ?
N2 O5 1.213(3) . ?
N3 O7 1.208(3) . ?
N3 O8 1.220(3) . ?
N4 O9 1.213(3) . ?
N4 O10 1.214(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
C3 C1 C2 122.9(2) 3_666 . ?
C3 C1 N1 117.9(2) 3_666 . ?
C2 C1 N1 119.2(2) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 C4 118.8(2) . . ?
C1 C2 C4 122.9(2) . . ?
C1 C3 C2 119.0(2) 3_666 . ?
C1 C3 H3 120.5 3_666 . ?
C2 C3 H3 120.5 . . ?
O4 C4 O3 123.5(2) . . ?
O4 C4 C2 124.7(2) . . ?
O3 C4 C2 111.7(2) . . ?
O3 C5 C6 106.1(2) . . ?
O3 C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
O3 C5 H5B 110.5 . . ?
C6 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
N4 C6 C5 114.3(2) . . ?
N4 C6 N2 106.7(2) . . ?
C5 C6 N2 109.2(2) . . ?
N4 C6 N3 107.4(2) . . ?
C5 C6 N3 111.6(2) . . ?
N2 C6 N3 107.4(2) . . ?
O2 N1 O1 124.4(2) . . ?
O2 N1 C1 117.4(2) . . ?
O1 N1 C1 118.2(2) . . ?
O6 N2 O5 127.4(2) . . ?
O6 N2 C6 118.5(2) . . ?
O5 N2 C6 114.1(2) . . ?
O7 N3 O8 128.0(2) . . ?
O7 N3 C6 117.4(2) . . ?
O8 N3 C6 114.6(2) . . ?
O9 N4 O10 127.2(3) . . ?
O9 N4 C6 116.3(2) . . ?
O10 N4 C6 116.5(2) . . ?
C4 O3 C5 113.60(19) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc1kl1kr
_database_code_depnum_ccdc_archive 'CCDC 1447314'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 N8 O20'
_chemical_formula_sum            'C12 H6 N8 O20'
_chemical_formula_weight         582.25

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   14.3744(16)
_cell_length_b                   8.2651(10)
_cell_length_c                   19.305(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.692(3)
_cell_angle_gamma                90.00
_cell_volume                     2131.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2554
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      24.63

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6968
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14475
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0495
_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       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.75
_reflns_number_total             3996
_reflns_number_gt                2614
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0221P)²+0.8399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3996
_refine_ls_number_parameters     389
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23756(14) 0.7399(2) 0.27842(10) 0.0189(4) Uani 1 1 d . . .
C2 C 0.14905(15) 0.8245(2) 0.25011(10) 0.0222(5) Uani 1 1 d . A .
H2 H 0.1149 0.8375 0.1979 0.027 Uiso 1 1 calc R . .
C3 C 0.11176(15) 0.8894(2) 0.30021(10) 0.0227(5) Uani 1 1 d D . .
C4 C 0.15923(14) 0.8721(2) 0.37663(10) 0.0210(5) Uani 1 1 d . A .
C5 C 0.24698(15) 0.7830(2) 0.40257(10) 0.0220(5) Uani 1 1 d . . .
H5 H 0.2803 0.7680 0.4547 0.026 Uiso 1 1 calc R A .
C6 C 0.28740(14) 0.7153(2) 0.35426(10) 0.0187(4) Uani 1 1 d . A .
C7 C 0.12192(16) 0.9395(3) 0.43417(11) 0.0241(5) Uani 1 1 d . . .
C8 C 0.16706(16) 1.1275(2) 0.53415(10) 0.0241(5) Uani 1 1 d . . .
H8A H 0.2208 1.0933 0.5810 0.029 Uiso 1 1 calc R A .
H8B H 0.1019 1.0913 0.5352 0.029 Uiso 1 1 calc R . .
C9 C 0.16798(15) 1.3084(3) 0.52544(10) 0.0228(5) Uani 1 1 d . A .
C10 C 0.38142(15) 0.6200(2) 0.38872(10) 0.0201(5) Uani 1 1 d . . .
C11 C 0.47380(14) 0.3962(2) 0.37494(10) 0.0218(5) Uani 1 1 d . . .
H11A H 0.5037 0.3987 0.4301 0.026 Uiso 1 1 calc R A .
H11B H 0.5224 0.4429 0.3552 0.026 Uiso 1 1 calc R . .
C12 C 0.44837(14) 0.2255(3) 0.34780(10) 0.0214(5) Uani 1 1 d . A .
N1 N 0.28258(13) 0.6854(2) 0.22492(9) 0.0241(4) Uani 1 1 d . . .
N3 N 0.07234(14) 1.3755(3) 0.46662(9) 0.0312(5) Uani 1 1 d . . .
N4 N 0.17896(14) 1.3945(3) 0.59795(10) 0.0335(5) Uani 1 1 d . . .
N5 N 0.25565(15) 1.3610(2) 0.50488(11) 0.0344(5) Uani 1 1 d . . .
N6 N 0.42126(13) 0.2054(2) 0.26378(9) 0.0282(4) Uani 1 1 d . . .
N7 N 0.53552(16) 0.1121(3) 0.38698(9) 0.0352(5) Uani 1 1 d . . .
N8 N 0.35942(15) 0.1650(2) 0.36513(11) 0.0342(5) Uani 1 1 d . . .
O1 O 0.37154(11) 0.71353(19) 0.24066(8) 0.0323(4) Uani 1 1 d . . .
O2 O 0.22733(12) 0.6207(2) 0.16784(8) 0.0413(4) Uani 1 1 d . . .
O5 O 0.18312(10) 1.05999(17) 0.47089(7) 0.0236(3) Uani 1 1 d . A .
O6 O 0.05496(13) 0.8868(2) 0.44863(10) 0.0572(6) Uani 1 1 d . A .
O7 O 0.01079(11) 1.2772(2) 0.43146(8) 0.0395(4) Uani 1 1 d . A .
O8 O 0.06629(14) 1.5219(2) 0.46076(10) 0.0574(5) Uani 1 1 d . A .
O9 O 0.14956(13) 1.3192(2) 0.63940(8) 0.0486(5) Uani 1 1 d . A .
O10 O 0.21380(15) 1.5296(2) 0.60720(10) 0.0615(6) Uani 1 1 d . A .
O11 O 0.33664(12) 1.3405(2) 0.55390(10) 0.0559(5) Uani 1 1 d . A .
O12 O 0.23773(14) 1.4093(2) 0.44212(10) 0.0557(5) Uani 1 1 d . A .
O13 O 0.38195(9) 0.48645(16) 0.34851(7) 0.0221(3) Uani 1 1 d . A .
O14 O 0.44637(10) 0.65484(18) 0.44640(7) 0.0297(4) Uani 1 1 d . A .
O15 O 0.40167(13) 0.3274(2) 0.22737(8) 0.0420(4) Uani 1 1 d . A .
O16 O 0.42063(14) 0.0690(2) 0.24124(9) 0.0528(5) Uani 1 1 d . A .
O17 O 0.61720(12) 0.1772(2) 0.41201(8) 0.0426(4) Uani 1 1 d . A .
O18 O 0.51652(16) -0.0299(2) 0.38932(10) 0.0671(6) Uani 1 1 d . A .
O19 O 0.37614(14) 0.1455(2) 0.43046(9) 0.0560(5) Uani 1 1 d . A .
O20 O 0.28093(13) 0.1472(2) 0.31321(10) 0.0531(5) Uani 1 1 d . A .
N2 N 0.0261(10) 1.0033(19) 0.2686(6) 0.030(2) Uani 0.59(5) 1 d PD A 1
O3 O 0.0144(16) 1.102(3) 0.3086(7) 0.067(5) Uani 0.59(5) 1 d PD A 1
O4 O -0.0244(9) 0.9966(16) 0.2046(5) 0.058(3) Uani 0.59(5) 1 d PD A 1
N2' N 0.0124(12) 0.968(3) 0.2726(8) 0.030(4) Uani 0.41(5) 1 d PD A 2
O3' O -0.0119(13) 1.040(4) 0.3171(7) 0.054(4) Uani 0.41(5) 1 d PD A 2
O4' O -0.0423(18) 0.947(6) 0.2105(8) 0.091(8) Uani 0.41(5) 1 d PD A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(3) . ?
C1 C6 1.387(3) . ?
C1 N1 1.477(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 N2' 1.477(11) . ?
C3 N2 1.489(8) . ?
C4 C5 1.385(3) . ?
C4 C7 1.507(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C10 1.491(3) . ?
C7 O6 1.180(2) . ?
C7 O5 1.344(2) . ?
C8 O5 1.437(2) . ?
C8 C9 1.505(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N5 1.518(3) . ?
C9 N4 1.526(2) . ?
C9 N3 1.527(3) . ?
C10 O14 1.194(2) . ?
C10 O13 1.351(2) . ?
C11 O13 1.436(2) . ?
C11 C12 1.502(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N8 1.521(3) . ?
C12 N7 1.523(3) . ?
C12 N6 1.531(2) . ?
N1 O2 1.218(2) . ?
N1 O1 1.222(2) . ?
N3 O7 1.208(2) . ?
N3 O8 1.215(2) . ?
N4 O9 1.207(2) . ?
N4 O10 1.210(2) . ?
N5 O12 1.210(2) . ?
N5 O11 1.210(2) . ?
N6 O15 1.202(2) . ?
N6 O16 1.207(2) . ?
N7 O18 1.210(3) . ?
N7 O17 1.218(2) . ?
N8 O19 1.204(2) . ?
N8 O20 1.210(2) . ?
N2 O3 1.179(8) . ?
N2 O4 1.181(8) . ?
N2' O4' 1.180(11) . ?
N2' O3' 1.197(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.36(17) . . ?
C2 C1 N1 117.19(16) . . ?
C6 C1 N1 120.31(17) . . ?
C1 C2 C3 117.54(17) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C2 C3 C4 122.80(19) . . ?
C2 C3 N2' 119.6(6) . . ?
C4 C3 N2' 117.3(6) . . ?
C2 C3 N2 115.9(5) . . ?
C4 C3 N2 120.6(5) . . ?
N2' C3 N2 14.6(10) . . ?
C5 C4 C3 117.68(18) . . ?
C5 C4 C7 117.04(17) . . ?
C3 C4 C7 125.27(18) . . ?
C4 C5 C6 121.58(18) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.01(18) . . ?
C5 C6 C10 116.69(16) . . ?
C1 C6 C10 125.30(17) . . ?
O6 C7 O5 125.52(19) . . ?
O6 C7 C4 125.5(2) . . ?
O5 C7 C4 108.70(17) . . ?
O5 C8 C9 106.26(15) . . ?
O5 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O5 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 N5 110.86(17) . . ?
C8 C9 N4 111.28(16) . . ?
N5 C9 N4 106.98(16) . . ?
C8 C9 N3 113.64(17) . . ?
N5 C9 N3 107.92(16) . . ?
N4 C9 N3 105.81(15) . . ?
O14 C10 O13 124.34(18) . . ?
O14 C10 C6 123.78(18) . . ?
O13 C10 C6 111.82(16) . . ?
O13 C11 C12 106.91(15) . . ?
O13 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O13 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 N8 110.35(16) . . ?
C11 C12 N7 110.80(17) . . ?
N8 C12 N7 107.02(17) . . ?
C11 C12 N6 113.91(16) . . ?
N8 C12 N6 106.98(15) . . ?
N7 C12 N6 107.46(15) . . ?
O2 N1 O1 125.49(17) . . ?
O2 N1 C1 117.30(17) . . ?
O1 N1 C1 117.17(16) . . ?
O7 N3 O8 127.21(19) . . ?
O7 N3 C9 116.40(18) . . ?
O8 N3 C9 116.38(19) . . ?
O9 N4 O10 127.3(2) . . ?
O9 N4 C9 115.16(19) . . ?
O10 N4 C9 117.6(2) . . ?
O12 N5 O11 128.1(2) . . ?
O12 N5 C9 117.80(19) . . ?
O11 N5 C9 114.02(19) . . ?
O15 N6 O16 127.15(18) . . ?
O15 N6 C12 116.20(17) . . ?
O16 N6 C12 116.64(18) . . ?
O18 N7 O17 127.7(2) . . ?
O18 N7 C12 117.4(2) . . ?
O17 N7 C12 114.9(2) . . ?
O19 N8 O20 128.0(2) . . ?
O19 N8 C12 114.57(18) . . ?
O20 N8 C12 117.41(18) . . ?
C7 O5 C8 117.16(15) . . ?
C10 O13 C11 114.84(14) . . ?
O3 N2 O4 122.4(8) . . ?
O3 N2 C3 117.9(7) . . ?
O4 N2 C3 119.6(8) . . ?
O4' N2' O3' 122.8(12) . . ?
O4' N2' C3 119.6(11) . . ?
O3' N2' C3 117.3(10) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.75
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc1kl1mt
_database_code_depnum_ccdc_archive 'CCDC 1447316'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H5 N9 O22'
_chemical_formula_sum            'C12 H5 N9 O22'
_chemical_formula_weight         627.25

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   13.8583(10)
_cell_length_b                   16.6279(13)
_cell_length_c                   10.0771(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.879(2)
_cell_angle_gamma                90.00
_cell_volume                     2254.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3239
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      25.08

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6774
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15134
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.39
_reflns_number_total             4063
_reflns_number_gt                2661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4063
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.50357(16) 0.26221(11) 0.2418(2) 0.0183(5) Uani 1 1 d . . .
C2 C 0.57291(15) 0.30356(12) 0.3406(2) 0.0180(5) Uani 1 1 d . . .
C3 C 0.56614(15) 0.38697(12) 0.3374(2) 0.0197(5) Uani 1 1 d . . .
C4 C 0.49545(16) 0.42817(12) 0.2412(2) 0.0220(5) Uani 1 1 d . . .
H4 H 0.4924 0.4852 0.2417 0.026 Uiso 1 1 calc R . .
C5 C 0.42949(15) 0.38368(13) 0.1444(2) 0.0209(5) Uani 1 1 d . . .
C6 C 0.43123(15) 0.30005(12) 0.1410(2) 0.0181(5) Uani 1 1 d . . .
C7 C 0.64973(16) 0.26059(12) 0.4498(2) 0.0199(5) Uani 1 1 d . . .
C8 C 0.78842(16) 0.17674(13) 0.4855(2) 0.0250(5) Uani 1 1 d . . .
H8A H 0.7571 0.1381 0.5370 0.030 Uiso 1 1 calc R . .
H8B H 0.8324 0.2129 0.5514 0.030 Uiso 1 1 calc R . .
C9 C 0.84706(15) 0.13265(12) 0.3993(2) 0.0198(5) Uani 1 1 d . . .
C10 C 0.35923(15) 0.25224(12) 0.0329(2) 0.0202(5) Uani 1 1 d . . .
C11 C 0.22748(16) 0.16142(12) -0.0027(2) 0.0229(5) Uani 1 1 d . . .
H11A H 0.2649 0.1171 -0.0327 0.027 Uiso 1 1 calc R . .
H11B H 0.1904 0.1910 -0.0844 0.027 Uiso 1 1 calc R . .
C12 C 0.15718(16) 0.12908(12) 0.0784(2) 0.0206(5) Uani 1 1 d . . .
N1 N 0.50522(13) 0.17326(10) 0.2458(2) 0.0250(4) Uani 1 1 d . . .
N2 N 0.87501(13) 0.18686(11) 0.29363(19) 0.0262(4) Uani 1 1 d . . .
N3 N 0.94444(14) 0.10136(11) 0.48902(19) 0.0266(4) Uani 1 1 d . . .
N4 N 0.79084(15) 0.06083(12) 0.32483(19) 0.0276(5) Uani 1 1 d . . .
N5 N 0.64025(14) 0.43476(11) 0.43534(17) 0.0246(4) Uani 1 1 d . . .
N6 N 0.35234(15) 0.42770(12) 0.04571(18) 0.0285(5) Uani 1 1 d . . .
N7 N 0.06830(14) 0.08937(11) -0.01781(19) 0.0281(5) Uani 1 1 d . . .
N8 N 0.11847(14) 0.19684(12) 0.1527(2) 0.0286(5) Uani 1 1 d . . .
N9 N 0.20348(15) 0.06547(11) 0.18339(18) 0.0248(4) Uani 1 1 d . . .
O1 O 0.48417(12) 0.13775(9) 0.13651(17) 0.0354(4) Uani 1 1 d . . .
O2 O 0.52671(12) 0.14153(9) 0.35834(17) 0.0346(4) Uani 1 1 d . . .
O3 O 0.71377(10) 0.22243(8) 0.39184(13) 0.0228(4) Uani 1 1 d . . .
O4 O 0.65236(11) 0.26165(9) 0.56878(14) 0.0278(4) Uani 1 1 d . . .
O5 O 0.86795(13) 0.15933(10) 0.17997(16) 0.0397(4) Uani 1 1 d . . .
O6 O 0.90372(12) 0.25331(10) 0.33461(17) 0.0411(4) Uani 1 1 d . . .
O7 O 1.01303(12) 0.09386(10) 0.43523(17) 0.0393(4) Uani 1 1 d . . .
O8 O 0.94186(13) 0.08584(10) 0.60517(17) 0.0425(5) Uani 1 1 d . . .
O9 O 0.83298(14) -0.00287(10) 0.33549(19) 0.0489(5) Uani 1 1 d . . .
O10 O 0.70611(13) 0.07459(11) 0.26233(18) 0.0465(5) Uani 1 1 d . . .
O11 O 0.72647(12) 0.41155(10) 0.45868(17) 0.0380(4) Uani 1 1 d . . .
O12 O 0.61099(12) 0.49471(9) 0.48283(15) 0.0337(4) Uani 1 1 d . . .
O13 O 0.27320(12) 0.39257(10) 0.00122(16) 0.0389(4) Uani 1 1 d . . .
O14 O 0.37076(14) 0.49581(10) 0.01658(17) 0.0490(5) Uani 1 1 d . . .
O15 O 0.29380(10) 0.21453(8) 0.08914(13) 0.0213(3) Uani 1 1 d . . .
O16 O 0.36217(11) 0.24825(9) -0.08429(15) 0.0308(4) Uani 1 1 d . . .
O17 O -0.01227(12) 0.09981(11) 0.00276(18) 0.0464(5) Uani 1 1 d . . .
O18 O 0.09063(13) 0.04809(11) -0.10500(17) 0.0464(5) Uani 1 1 d . . .
O19 O 0.12817(12) 0.19016(10) 0.27452(17) 0.0393(4) Uani 1 1 d . . .
O20 O 0.08200(13) 0.25252(10) 0.07944(18) 0.0453(5) Uani 1 1 d . . .
O21 O 0.14698(13) 0.01954(10) 0.21833(16) 0.0439(5) Uani 1 1 d . . .
O22 O 0.29347(12) 0.06731(10) 0.22171(16) 0.0335(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
C1 C2 1.388(3) . ?
C1 C6 1.394(3) . ?
C1 N1 1.480(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.514(3) . ?
C3 C4 1.383(3) . ?
C3 N5 1.474(3) . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 N6 1.469(3) . ?
C6 C10 1.514(3) . ?
C7 O4 1.191(2) . ?
C7 O3 1.334(2) . ?
C8 O3 1.438(2) . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.515(3) . ?
C9 N4 1.522(3) . ?
C9 N3 1.524(3) . ?
C10 O16 1.193(2) . ?
C10 O15 1.335(2) . ?
C11 O15 1.440(2) . ?
C11 C12 1.513(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N8 1.520(3) . ?
C12 N7 1.523(3) . ?
C12 N9 1.525(3) . ?
N1 O2 1.221(2) . ?
N1 O1 1.222(2) . ?
N2 O6 1.213(2) . ?
N2 O5 1.215(2) . ?
N3 O8 1.208(2) . ?
N3 O7 1.208(2) . ?
N4 O9 1.202(2) . ?
N4 O10 1.214(2) . ?
N5 O12 1.217(2) . ?
N5 O11 1.224(2) . ?
N6 O14 1.212(2) . ?
N6 O13 1.228(2) . ?
N7 O17 1.196(2) . ?
N7 O18 1.212(2) . ?
N8 O19 1.208(2) . ?
N8 O20 1.216(2) . ?
N9 O21 1.205(2) . ?
N9 O22 1.214(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 123.49(18) . . ?
C2 C1 N1 118.16(18) . . ?
C6 C1 N1 118.33(18) . . ?
C1 C2 C3 116.52(18) . . ?
C1 C2 C7 122.16(18) . . ?
C3 C2 C7 121.29(18) . . ?
C4 C3 C2 122.87(19) . . ?
C4 C3 N5 117.70(18) . . ?
C2 C3 N5 119.35(19) . . ?
C5 C4 C3 117.87(19) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 122.70(19) . . ?
C4 C5 N6 117.54(19) . . ?
C6 C5 N6 119.70(19) . . ?
C5 C6 C1 116.54(19) . . ?
C5 C6 C10 122.02(19) . . ?
C1 C6 C10 121.44(18) . . ?
O4 C7 O3 125.8(2) . . ?
O4 C7 C2 124.83(18) . . ?
O3 C7 C2 109.38(16) . . ?
O3 C8 C9 106.28(15) . . ?
O3 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O3 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 N2 112.22(17) . . ?
C8 C9 N4 112.41(17) . . ?
N2 C9 N4 107.90(16) . . ?
C8 C9 N3 110.24(16) . . ?
N2 C9 N3 106.30(15) . . ?
N4 C9 N3 107.48(16) . . ?
O16 C10 O15 125.57(19) . . ?
O16 C10 C6 124.61(19) . . ?
O15 C10 C6 109.81(16) . . ?
O15 C11 C12 105.36(15) . . ?
O15 C11 H11A 110.7 . . ?
C12 C11 H11A 110.7 . . ?
O15 C11 H11B 110.7 . . ?
C12 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C11 C12 N8 110.60(16) . . ?
C11 C12 N7 109.72(16) . . ?
N8 C12 N7 107.92(17) . . ?
C11 C12 N9 113.78(18) . . ?
N8 C12 N9 108.18(16) . . ?
N7 C12 N9 106.40(16) . . ?
O2 N1 O1 125.50(18) . . ?
O2 N1 C1 117.12(17) . . ?
O1 N1 C1 117.37(18) . . ?
O6 N2 O5 127.57(19) . . ?
O6 N2 C9 114.90(17) . . ?
O5 N2 C9 117.52(18) . . ?
O8 N3 O7 128.48(19) . . ?
O8 N3 C9 114.83(17) . . ?
O7 N3 C9 116.68(17) . . ?
O9 N4 O10 127.0(2) . . ?
O9 N4 C9 117.85(19) . . ?
O10 N4 C9 115.16(18) . . ?
O12 N5 O11 125.80(19) . . ?
O12 N5 C3 117.42(18) . . ?
O11 N5 C3 116.75(18) . . ?
O14 N6 O13 125.3(2) . . ?
O14 N6 C5 117.9(2) . . ?
O13 N6 C5 116.83(19) . . ?
O17 N7 O18 128.2(2) . . ?
O17 N7 C12 118.21(19) . . ?
O18 N7 C12 113.50(18) . . ?
O19 N8 O20 128.0(2) . . ?
O19 N8 C12 117.78(18) . . ?
O20 N8 C12 114.21(18) . . ?
O21 N9 O22 127.79(19) . . ?
O21 N9 C12 116.59(19) . . ?
O22 N9 C12 115.62(17) . . ?
C7 O3 C8 114.42(15) . . ?
C10 O15 C11 114.13(14) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/cc1kl1qx
_database_code_depnum_ccdc_archive 'CCDC 1447319'
_audit_update_record             
;
2016-01-14 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H4 N6 O14'
_chemical_formula_sum            'C9 H4 N6 O14'
_chemical_formula_weight         420.18

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   5.8335(4)
_cell_length_b                   10.1818(8)
_cell_length_c                   25.563(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.540(3)
_cell_angle_gamma                90.00
_cell_volume                     1508.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    2009
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      25.97

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6908
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2748
_reflns_number_gt                1924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2748
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6687(3) 0.80559(19) 0.17613(8) 0.0262(5) Uani 1 1 d . . .
C2 C 0.7284(3) 0.83682(18) 0.12637(8) 0.0217(4) Uani 1 1 d . . .
C3 C 0.9076(3) 0.76307(18) 0.10936(8) 0.0231(5) Uani 1 1 d . . .
C4 C 1.0290(3) 0.67025(19) 0.14072(8) 0.0273(5) Uani 1 1 d . . .
H4 H 1.1511 0.6218 0.1284 0.033 Uiso 1 1 calc R . .
C5 C 0.9671(3) 0.65039(19) 0.19042(9) 0.0285(5) Uani 1 1 d . . .
C6 C 0.7844(3) 0.7136(2) 0.20891(9) 0.0292(5) Uani 1 1 d . . .
H6 H 0.7398 0.6948 0.2427 0.035 Uiso 1 1 calc R . .
C7 C 0.5969(3) 0.93844(19) 0.09219(8) 0.0235(5) Uani 1 1 d . . .
C8 C 0.5973(3) 1.15403(17) 0.06264(8) 0.0208(4) Uani 1 1 d . . .
H8A H 0.4274 1.1464 0.0608 0.025 Uiso 1 1 calc R . .
H8B H 0.6423 1.1451 0.0266 0.025 Uiso 1 1 calc R . .
C9 C 0.6761(3) 1.28462(19) 0.08589(8) 0.0214(4) Uani 1 1 d . . .
N1 N 0.4713(3) 0.87371(19) 0.19538(7) 0.0320(4) Uani 1 1 d . . .
N2 N 0.9199(3) 1.32113(18) 0.07615(7) 0.0276(4) Uani 1 1 d . . .
N3 N 0.5194(3) 1.39441(17) 0.06248(8) 0.0285(4) Uani 1 1 d . . .
N4 N 0.6686(3) 1.28938(17) 0.14513(7) 0.0294(4) Uani 1 1 d . . .
N5 N 0.9681(3) 0.78047(16) 0.05517(7) 0.0254(4) Uani 1 1 d . . .
N6 N 1.1053(3) 0.55746(17) 0.22596(8) 0.0386(5) Uani 1 1 d . . .
O1 O 0.3733(2) 0.81612(16) 0.22836(6) 0.0422(4) Uani 1 1 d . . .
O2 O 0.4176(3) 0.98112(18) 0.17712(7) 0.0547(5) Uani 1 1 d . . .
O3 O 0.7064(2) 1.05403(12) 0.09635(5) 0.0206(3) Uani 1 1 d . . .
O4 O 0.4196(2) 0.91682(14) 0.06526(6) 0.0363(4) Uani 1 1 d . . .
O5 O 1.0564(2) 1.23112(15) 0.08043(7) 0.0390(4) Uani 1 1 d . . .
O6 O 0.9579(2) 1.43439(15) 0.06552(7) 0.0416(4) Uani 1 1 d . . .
O7 O 0.4320(2) 1.37563(14) 0.01775(6) 0.0346(4) Uani 1 1 d . . .
O8 O 0.4982(3) 1.48966(14) 0.09006(7) 0.0456(5) Uani 1 1 d . . .
O9 O 0.4866(2) 1.25481(15) 0.15908(6) 0.0393(4) Uani 1 1 d . . .
O10 O 0.8414(3) 1.32596(19) 0.17219(6) 0.0524(5) Uani 1 1 d . . .
O11 O 1.1061(2) 0.70337(14) 0.04000(6) 0.0339(4) Uani 1 1 d . . .
O12 O 0.8757(3) 0.86969(14) 0.02875(6) 0.0375(4) Uani 1 1 d . . .
O13 O 1.2638(3) 0.50101(17) 0.20827(8) 0.0562(5) Uani 1 1 d . . .
O14 O 1.0538(3) 0.54521(17) 0.27042(7) 0.0527(5) 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
C1 C6 1.381(3) . ?
C1 C2 1.393(3) . ?
C1 N1 1.476(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.507(3) . ?
C3 C4 1.381(3) . ?
C3 N5 1.479(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 N6 1.485(3) . ?
C6 H6 0.9500 . ?
C7 O4 1.196(2) . ?
C7 O3 1.337(2) . ?
C8 O3 1.435(2) . ?
C8 C9 1.507(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.518(2) . ?
C9 N4 1.521(3) . ?
C9 N3 1.523(2) . ?
N1 O2 1.216(2) . ?
N1 O1 1.221(2) . ?
N2 O5 1.211(2) . ?
N2 O6 1.211(2) . ?
N3 O7 1.213(2) . ?
N3 O8 1.213(2) . ?
N4 O9 1.210(2) . ?
N4 O10 1.214(2) . ?
N5 O11 1.219(2) . ?
N5 O12 1.220(2) . ?
N6 O14 1.215(3) . ?
N6 O13 1.219(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 123.58(19) . . ?
C6 C1 N1 117.57(19) . . ?
C2 C1 N1 118.86(18) . . ?
C1 C2 C3 115.82(18) . . ?
C1 C2 C7 121.51(17) . . ?
C3 C2 C7 122.58(18) . . ?
C4 C3 C2 122.7(2) . . ?
C4 C3 N5 117.67(17) . . ?
C2 C3 N5 119.64(18) . . ?
C5 C4 C3 117.76(19) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C6 C5 C4 123.0(2) . . ?
C6 C5 N6 118.5(2) . . ?
C4 C5 N6 118.54(19) . . ?
C5 C6 C1 117.0(2) . . ?
C5 C6 H6 121.5 . . ?
C1 C6 H6 121.5 . . ?
O4 C7 O3 125.57(18) . . ?
O4 C7 C2 123.86(18) . . ?
O3 C7 C2 110.56(15) . . ?
O3 C8 C9 107.15(15) . . ?
O3 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O3 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C8 C9 N2 113.64(16) . . ?
C8 C9 N4 112.26(16) . . ?
N2 C9 N4 106.81(15) . . ?
C8 C9 N3 110.51(15) . . ?
N2 C9 N3 106.72(14) . . ?
N4 C9 N3 106.49(15) . . ?
O2 N1 O1 125.20(19) . . ?
O2 N1 C1 118.12(18) . . ?
O1 N1 C1 116.68(19) . . ?
O5 N2 O6 127.29(16) . . ?
O5 N2 C9 114.74(16) . . ?
O6 N2 C9 117.96(16) . . ?
O7 N3 O8 127.89(18) . . ?
O7 N3 C9 115.06(16) . . ?
O8 N3 C9 117.04(17) . . ?
O9 N4 O10 128.34(19) . . ?
O9 N4 C9 114.20(16) . . ?
O10 N4 C9 117.46(16) . . ?
O11 N5 O12 124.70(18) . . ?
O11 N5 C3 117.23(17) . . ?
O12 N5 C3 118.07(16) . . ?
O14 N6 O13 125.3(2) . . ?
O14 N6 C5 117.6(2) . . ?
O13 N6 C5 117.1(2) . . ?
C7 O3 C8 113.67(14) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
