# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_comp16
_database_code_depnum_ccdc_archive 'CCDC 1434738'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H6 N12 O21'
_chemical_formula_sum            'C9 H6 N12 O21'
_chemical_formula_weight         618.26

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n '

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   10.9186(15)
_cell_length_b                   17.007(2)
_cell_length_c                   35.300(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6555.0(15)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3781
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.26

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3744
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            80248
_diffrn_reflns_av_R_equivalents  0.1717
_diffrn_reflns_av_sigmaI/netI    0.0986
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         30.20
_reflns_number_total             9824
_reflns_number_gt                6038
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'

_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)+(0.1031P)²+6.8440P] 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         9824
_refine_ls_number_parameters     1134
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2113
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
O1 O 0.2836(4) 0.3443(3) 0.48358(15) 0.0199(10) Uani 1 1 d . . .
O2 O 0.3243(6) 0.1806(4) 0.42934(18) 0.0352(14) Uani 1 1 d . . .
O3 O 0.3886(5) 0.1912(3) 0.48799(18) 0.0289(13) Uani 1 1 d . . .
O4 O 0.1206(5) 0.2988(3) 0.42558(16) 0.0299(13) Uani 1 1 d . . .
O5 O 0.0402(6) 0.1818(4) 0.43096(18) 0.0390(16) Uani 1 1 d . . .
O6 O 0.1701(6) 0.0882(3) 0.49208(19) 0.0332(14) Uani 1 1 d . . .
O7 O 0.0448(5) 0.1716(3) 0.51796(17) 0.0290(12) Uani 1 1 d . . .
O8 O 0.4089(5) 0.5841(3) 0.44635(17) 0.0258(12) Uani 1 1 d . . .
O9 O 0.5367(8) 0.7318(4) 0.4042(3) 0.066(3) Uani 1 1 d . . .
O10 O 0.6338(7) 0.6997(4) 0.4567(2) 0.055(2) Uani 1 1 d . . .
O11 O 0.4441(6) 0.5958(5) 0.3676(2) 0.0450(17) Uani 1 1 d . . .
O12 O 0.6398(6) 0.5770(4) 0.35095(18) 0.0407(15) Uani 1 1 d . . .
O13 O 0.8044(6) 0.6310(4) 0.4052(2) 0.0507(19) Uani 1 1 d . . .
O14 O 0.7563(6) 0.5136(4) 0.4265(2) 0.0442(17) Uani 1 1 d . . .
O15 O 0.0194(5) 0.5494(3) 0.49104(15) 0.0232(11) Uani 1 1 d . . .
O16 O -0.2322(6) 0.5794(4) 0.5129(2) 0.0459(17) Uani 1 1 d . . .
O17 O -0.1629(8) 0.5781(4) 0.5708(2) 0.054(2) Uani 1 1 d . . .
O18 O 0.0967(7) 0.6041(4) 0.5608(2) 0.054(2) Uani 1 1 d . . .
O19 O 0.0314(6) 0.7213(3) 0.57566(19) 0.0359(14) Uani 1 1 d . . .
O20 O -0.2203(6) 0.7431(4) 0.5406(2) 0.0413(16) Uani 1 1 d . . .
O21 O -0.0770(7) 0.7811(4) 0.5015(2) 0.0460(18) Uani 1 1 d . . .
N1 N 0.3450(6) 0.4608(3) 0.46243(18) 0.0199(12) Uani 1 1 d . . .
N2 N 0.2151(6) 0.5721(4) 0.46815(18) 0.0209(13) Uani 1 1 d . . .
N3 N 0.1437(6) 0.4462(3) 0.48762(19) 0.0215(13) Uani 1 1 d . . .
N4 N 0.3102(6) 0.1945(4) 0.4621(2) 0.0249(14) Uani 1 1 d . . .
N5 N 0.1074(6) 0.2342(4) 0.44061(18) 0.0216(13) Uani 1 1 d . . .
N6 N 0.1284(6) 0.1544(4) 0.49738(19) 0.0236(14) Uani 1 1 d . . .
N7 N 0.5894(8) 0.6865(4) 0.4257(2) 0.0387(19) Uani 1 1 d . . .
N8 N 0.5581(8) 0.5903(5) 0.3730(2) 0.0375(18) Uani 1 1 d . . .
N9 N 0.7311(7) 0.5772(4) 0.4156(2) 0.0356(17) Uani 1 1 d . . .
N10 N -0.1613(7) 0.5974(4) 0.5374(2) 0.0301(15) Uani 1 1 d . . .
N11 N 0.0300(7) 0.6598(4) 0.5577(2) 0.0292(15) Uani 1 1 d . . .
N12 N -0.1265(7) 0.7337(4) 0.5222(2) 0.0296(15) Uani 1 1 d . . .
C1 C 0.2541(6) 0.4198(4) 0.47762(19) 0.0153(13) Uani 1 1 d . . .
C2 C 0.3201(7) 0.5362(4) 0.4592(2) 0.0209(15) Uani 1 1 d . . .
C3 C 0.1321(7) 0.5229(4) 0.4814(2) 0.0188(14) Uani 1 1 d . . .
C4 C 0.1928(7) 0.2945(4) 0.5007(2) 0.0194(14) Uani 1 1 d . . .
H4A H 0.1127 0.3217 0.5018 0.023 Uiso 1 1 calc R . .
H4B H 0.2174 0.2799 0.5267 0.023 Uiso 1 1 calc R . .
C5 C 0.1846(6) 0.2216(4) 0.4756(2) 0.0175(14) Uani 1 1 d . . .
C6 C 0.5254(7) 0.5480(5) 0.4411(2) 0.0235(15) Uani 1 1 d . . .
H6A H 0.5158 0.4950 0.4299 0.028 Uiso 1 1 calc R . .
H6B H 0.5685 0.5429 0.4657 0.028 Uiso 1 1 calc R . .
C7 C 0.5968(7) 0.6011(5) 0.4146(3) 0.0287(17) Uani 1 1 d . . .
C8 C -0.0023(8) 0.6311(4) 0.4879(2) 0.0265(17) Uani 1 1 d . . .
H8A H -0.0578 0.6426 0.4664 0.032 Uiso 1 1 calc R . .
H8B H 0.0755 0.6601 0.4841 0.032 Uiso 1 1 calc R . .
C9 C -0.0621(7) 0.6540(4) 0.5258(2) 0.0215(15) Uani 1 1 d . . .
O1' O 0.3912(5) 0.0170(3) 0.28833(14) 0.0192(11) Uani 1 1 d . . .
O2' O 0.5029(8) 0.1411(3) 0.3512(2) 0.050(2) Uani 1 1 d . . .
O3' O 0.3426(6) 0.0664(4) 0.36174(17) 0.0344(14) Uani 1 1 d . . .
O4' O 0.6493(6) 0.0470(5) 0.29412(19) 0.052(2) Uani 1 1 d . . .
O5' O 0.7289(6) 0.0290(5) 0.3490(2) 0.057(2) Uani 1 1 d . . .
O6' O 0.5329(6) -0.0071(4) 0.40697(18) 0.0416(16) Uani 1 1 d . . .
O7' O 0.5634(7) -0.1110(4) 0.37173(19) 0.0409(16) Uani 1 1 d . . .
O8' O 0.3471(5) 0.1545(3) 0.18085(15) 0.0179(10) Uani 1 1 d . . .
O9' O 0.4029(6) 0.3404(4) 0.1376(2) 0.0428(17) Uani 1 1 d . . .
O10' O 0.4729(5) 0.3003(3) 0.19199(19) 0.0302(13) Uani 1 1 d . . .
O11' O 0.1948(5) 0.2228(3) 0.12661(16) 0.0293(13) Uani 1 1 d . . .
O12' O 0.1212(8) 0.3362(4) 0.1397(2) 0.051(2) Uani 1 1 d . . .
O13' O 0.2629(6) 0.4130(3) 0.20387(18) 0.0351(15) Uani 1 1 d . . .
O14' O 0.1250(5) 0.3310(3) 0.22388(16) 0.0232(11) Uani 1 1 d . . .
O15' O 0.5669(5) -0.0706(3) 0.17910(15) 0.0207(11) Uani 1 1 d . . .
O16' O 0.7562(5) -0.1765(3) 0.15541(16) 0.0245(12) Uani 1 1 d . . .
O17' O 0.6057(5) -0.2600(3) 0.15332(16) 0.0267(12) Uani 1 1 d . . .
O18' O 0.3831(6) -0.1579(4) 0.1384(2) 0.0388(15) Uani 1 1 d . . .
O19' O 0.4455(5) -0.2146(4) 0.08706(18) 0.0317(13) Uani 1 1 d . . .
O20' O 0.7225(5) -0.1841(3) 0.07469(16) 0.0289(13) Uani 1 1 d . . .
O21' O 0.6043(6) -0.0843(3) 0.06227(16) 0.0319(14) Uani 1 1 d . . .
N1' N 0.3669(5) 0.0850(3) 0.23541(16) 0.0153(11) Uani 1 1 d . . .
N2' N 0.4614(5) 0.0452(3) 0.17805(17) 0.0150(11) Uani 1 1 d . . .
N3' N 0.4864(5) -0.0313(3) 0.23443(17) 0.0154(12) Uani 1 1 d . . .
N4' N 0.4472(8) 0.0797(4) 0.3529(2) 0.0323(17) Uani 1 1 d . . .
N5' N 0.6444(7) 0.0311(5) 0.3273(2) 0.0372(19) Uani 1 1 d . . .
N6' N 0.5392(7) -0.0427(4) 0.3772(2) 0.0295(15) Uani 1 1 d . . .
N7' N 0.3922(6) 0.3107(3) 0.1696(2) 0.0234(14) Uani 1 1 d . . .
N8' N 0.1866(6) 0.2806(3) 0.14604(18) 0.0201(13) Uani 1 1 d . . .
N9' N 0.2145(6) 0.3484(3) 0.20543(19) 0.0198(13) Uani 1 1 d . . .
N10' N 0.6556(5) -0.1978(3) 0.14531(17) 0.0163(12) Uani 1 1 d . . .
N11' N 0.4586(5) -0.1735(3) 0.11454(19) 0.0187(12) Uani 1 1 d . . .
N12' N 0.6437(6) -0.1363(4) 0.08221(18) 0.0206(13) Uani 1 1 d . . .
C1' C 0.4185(6) 0.0228(4) 0.2514(2) 0.0149(13) Uani 1 1 d . . .
C2' C 0.3921(6) 0.0935(4) 0.2000(2) 0.0164(14) Uani 1 1 d . . .
C3' C 0.5019(6) -0.0159(3) 0.19756(18) 0.0113(12) Uani 1 1 d . . .
C4' C 0.4474(7) -0.0404(4) 0.3116(2) 0.0176(14) Uani 1 1 d . . .
H4'A H 0.5031 -0.0740 0.2965 0.021 Uiso 1 1 calc R . .
H4'B H 0.3847 -0.0742 0.3237 0.021 Uiso 1 1 calc R . .
C5' C 0.5189(6) 0.0052(4) 0.3416(2) 0.0160(14) Uani 1 1 d . . .
C6' C 0.2718(6) 0.2063(4) 0.2033(2) 0.0165(13) Uani 1 1 d . . .
H6'A H 0.3086 0.2147 0.2286 0.020 Uiso 1 1 calc R . .
H6'B H 0.1887 0.1840 0.2065 0.020 Uiso 1 1 calc R . .
C7' C 0.2665(6) 0.2824(4) 0.1813(2) 0.0148(13) Uani 1 1 d . . .
C8' C 0.5868(7) -0.0582(4) 0.1392(2) 0.0212(16) Uani 1 1 d . . .
H8'A H 0.6664 -0.0319 0.1348 0.025 Uiso 1 1 calc R . .
H8'B H 0.5209 -0.0252 0.1283 0.025 Uiso 1 1 calc R . .
C9' C 0.5859(7) -0.1408(4) 0.1213(2) 0.0194(15) Uani 1 1 d . . .
O1" O 0.7042(5) 0.5150(3) 0.14666(14) 0.0184(10) Uani 1 1 d . A .
O2" O 0.5957(6) 0.6390(3) 0.08502(19) 0.0367(15) Uani 1 1 d . . .
O3" O 0.7394(6) 0.5594(4) 0.06648(17) 0.0360(15) Uani 1 1 d . . .
O4" O 0.4466(7) 0.5462(5) 0.14335(19) 0.0453(18) Uani 1 1 d . . .
O5" O 0.3651(6) 0.5394(4) 0.0876(2) 0.0442(17) Uani 1 1 d . . .
O6" O 0.5406(6) 0.4819(3) 0.02925(15) 0.0340(15) Uani 1 1 d . A .
O7"A O 0.5344(11) 0.3818(6) 0.0679(3) 0.018(2) Uiso 0.51 1 d P A 1
O7"B O 0.4846(12) 0.3895(7) 0.0702(3) 0.026(3) Uiso 0.49 1 d P A 2
O8" O 0.7461(4) 0.6530(3) 0.25483(14) 0.0172(10) Uani 1 1 d . . .
O9" O 0.6928(6) 0.8383(4) 0.29969(19) 0.0386(15) Uani 1 1 d . . .
O10" O 0.6226(5) 0.8019(3) 0.24447(19) 0.0298(13) Uani 1 1 d . . .
O11" O 0.8790(7) 0.7204(3) 0.31308(19) 0.0384(16) Uani 1 1 d . . .
O12" O 0.9910(6) 0.8179(4) 0.29524(18) 0.0343(14) Uani 1 1 d . . .
O13" O 0.8431(5) 0.9124(3) 0.23790(19) 0.0323(14) Uani 1 1 d . . .
O14" O 0.9673(5) 0.8277(3) 0.21262(15) 0.0205(11) Uani 1 1 d . . .
O15" O 0.5237(5) 0.4278(3) 0.25424(14) 0.0177(10) Uani 1 1 d . . .
O16" O 0.3337(5) 0.3218(3) 0.27959(17) 0.0277(12) Uani 1 1 d . . .
O17" O 0.4860(6) 0.2385(3) 0.28223(16) 0.0249(12) Uani 1 1 d . . .
O18" O 0.7075(5) 0.3429(4) 0.29492(17) 0.0313(14) Uani 1 1 d . . .
O19" O 0.6489(5) 0.2895(4) 0.34836(18) 0.0321(14) Uani 1 1 d . . .
O20" O 0.3705(5) 0.3167(3) 0.36057(15) 0.0249(12) Uani 1 1 d . . .
O21" O 0.4818(5) 0.4230(3) 0.37022(15) 0.0248(12) Uani 1 1 d . . .
N1" N 0.7277(5) 0.5851(3) 0.19893(17) 0.0156(11) Uani 1 1 d . . .
N2" N 0.6315(5) 0.5432(3) 0.25568(17) 0.0161(12) Uani 1 1 d . . .
N3" N 0.6081(5) 0.4672(3) 0.19978(16) 0.0137(11) Uani 1 1 d . . .
N4" N 0.6419(7) 0.5738(4) 0.08015(18) 0.0232(14) Uani 1 1 d . . .
N5" N 0.4494(6) 0.5316(4) 0.11029(19) 0.0251(14) Uani 1 1 d . . .
N6" N 0.5383(6) 0.4533(3) 0.06075(18) 0.0216(13) Uani 1 1 d . . .
N7" N 0.7013(6) 0.8089(4) 0.2689(2) 0.0239(14) Uani 1 1 d . . .
N8" N 0.9066(6) 0.7727(4) 0.29235(19) 0.0221(13) Uani 1 1 d . . .
N9" N 0.8824(6) 0.8471(4) 0.23275(19) 0.0221(13) Uani 1 1 d . . .
N10" N 0.4360(6) 0.2996(4) 0.29017(18) 0.0205(13) Uani 1 1 d . . .
N11" N 0.6330(6) 0.3274(4) 0.31960(19) 0.0239(14) Uani 1 1 d . . .
N12" N 0.4449(6) 0.3664(3) 0.35158(17) 0.0175(12) Uani 1 1 d . . .
C1" C 0.6758(6) 0.5215(4) 0.1828(2) 0.0164(14) Uani 1 1 d . . .
C2" C 0.7005(6) 0.5915(4) 0.23500(19) 0.0134(13) Uani 1 1 d . . .
C3" C 0.5910(6) 0.4826(4) 0.2364(2) 0.0177(14) Uani 1 1 d . . .
C4" C 0.6456(7) 0.4581(4) 0.1231(2) 0.0180(14) Uani 1 1 d . . .
H4"A H 0.5921 0.4235 0.1384 0.022 Uiso 1 1 calc R A .
H4"B H 0.7074 0.4251 0.1101 0.022 Uiso 1 1 calc R . .
C5" C 0.5703(7) 0.5037(4) 0.0943(2) 0.0214(16) Uani 1 1 d . A .
C6" C 0.8204(6) 0.7061(4) 0.2332(2) 0.0165(14) Uani 1 1 d . . .
H6"A H 0.7824 0.7166 0.2082 0.020 Uiso 1 1 calc R . .
H6"B H 0.9030 0.6838 0.2291 0.020 Uiso 1 1 calc R . .
C7" C 0.8281(6) 0.7818(4) 0.2565(2) 0.0155(13) Uani 1 1 d . . .
C8" C 0.5034(8) 0.4395(4) 0.2940(2) 0.0206(15) Uani 1 1 d . . .
H8"A H 0.4231 0.4652 0.2982 0.025 Uiso 1 1 calc R . .
H8"B H 0.5680 0.4739 0.3047 0.025 Uiso 1 1 calc R . .
C9" C 0.5060(7) 0.3598(4) 0.3135(2) 0.0153(13) 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 C1 1.340(8) . ?
O1 C4 1.437(8) . ?
O2 N4 1.190(9) . ?
O3 N4 1.254(9) . ?
O4 N5 1.229(8) . ?
O5 N5 1.204(8) . ?
O6 N6 1.229(8) . ?
O7 N6 1.203(9) . ?
O8 C2 1.346(9) . ?
O8 C6 1.424(9) . ?
O9 N7 1.224(11) . ?
O10 N7 1.219(12) . ?
O11 N8 1.262(10) . ?
O12 N8 1.206(10) . ?
O13 N9 1.269(10) . ?
O14 N9 1.180(10) . ?
O15 C3 1.354(9) . ?
O15 C8 1.415(9) . ?
O16 N10 1.200(10) . ?
O17 N10 1.224(10) . ?
O18 N11 1.198(9) . ?
O19 N11 1.223(9) . ?
O20 N12 1.224(9) . ?
O21 N12 1.215(9) . ?
N1 C2 1.316(9) . ?
N1 C1 1.325(9) . ?
N2 C3 1.319(9) . ?
N2 C2 1.336(10) . ?
N3 C3 1.330(9) . ?
N3 C1 1.334(9) . ?
N4 C5 1.524(9) . ?
N5 C5 1.512(10) . ?
N6 C5 1.506(9) . ?
N7 C7 1.506(11) . ?
N8 C7 1.539(12) . ?
N9 C7 1.522(11) . ?
N10 C9 1.505(10) . ?
N11 C9 1.513(10) . ?
N12 C9 1.533(10) . ?
C4 C5 1.526(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.518(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.540(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O1' C1' 1.340(9) . ?
O1' C4' 1.417(8) . ?
O2' N4' 1.210(10) . ?
O3' N4' 1.205(10) . ?
O4' N5' 1.204(10) . ?
O5' N5' 1.199(10) . ?
O6' N6' 1.213(10) . ?
O7' N6' 1.207(9) . ?
O8' C2' 1.332(8) . ?
O8' C6' 1.441(8) . ?
O9' N7' 1.241(10) . ?
O10' N7' 1.197(9) . ?
O11' N8' 1.202(8) . ?
O12' N8' 1.205(8) . ?
O13' N9' 1.220(8) . ?
O14' N9' 1.212(8) . ?
O15' C3' 1.340(8) . ?
O15' C8' 1.440(9) . ?
O16' N10' 1.211(8) . ?
O17' N10' 1.223(8) . ?
O18' N11' 1.207(9) . ?
O19' N11' 1.205(9) . ?
O20' N12' 1.212(8) . ?
O21' N12' 1.209(8) . ?
N1' C2' 1.289(9) . ?
N1' C1' 1.326(9) . ?
N2' C3' 1.322(9) . ?
N2' C2' 1.359(9) . ?
N3' C1' 1.326(9) . ?
N3' C3' 1.339(9) . ?
N4' C5' 1.541(10) . ?
N5' C5' 1.525(10) . ?
N6' C5' 1.515(10) . ?
N7' C7' 1.513(9) . ?
N8' C7' 1.522(10) . ?
N9' C7' 1.518(9) . ?
N10' C9' 1.495(9) . ?
N11' C9' 1.516(9) . ?
N12' C9' 1.520(10) . ?
C4' C5' 1.527(10) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C6' C7' 1.510(10) . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C8' C9' 1.540(9) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
O1" C1" 1.318(9) . ?
O1" C4" 1.428(8) . ?
O2" N4" 1.229(8) . ?
O3" N4" 1.194(9) . ?
O4" N5" 1.194(9) . ?
O5" N5" 1.227(9) . ?
O6" N6" 1.214(8) . ?
O7"A N6" 1.243(12) . ?
O7"B N6" 1.278(14) . ?
O8" C2" 1.354(8) . ?
O8" C6" 1.434(8) . ?
O9" N7" 1.201(9) . ?
O10" N7" 1.223(9) . ?
O11" N8" 1.191(9) . ?
O12" N8" 1.204(8) . ?
O13" N9" 1.204(8) . ?
O14" N9" 1.214(8) . ?
O15" C3" 1.343(8) . ?
O15" C8" 1.436(9) . ?
O16" N10" 1.236(8) . ?
O17" N10" 1.206(8) . ?
O18" N11" 1.220(8) . ?
O19" N11" 1.216(8) . ?
O20" N12" 1.215(8) . ?
O21" N12" 1.234(8) . ?
N1" C2" 1.312(9) . ?
N1" C1" 1.347(9) . ?
N2" C3" 1.312(9) . ?
N2" C2" 1.332(8) . ?
N3" C1" 1.325(9) . ?
N3" C3" 1.332(9) . ?
N4" C5" 1.512(10) . ?
N5" C5" 1.513(10) . ?
N6" C5" 1.503(10) . ?
N7" C7" 1.524(9) . ?
N8" C7" 1.536(10) . ?
N9" C7" 1.513(9) . ?
N10" C9" 1.520(9) . ?
N11" C9" 1.507(10) . ?
N12" C9" 1.506(9) . ?
C4" C5" 1.520(10) . ?
C4" H4"A 0.9900 . ?
C4" H4"B 0.9900 . ?
C6" C7" 1.529(9) . ?
C6" H6"A 0.9900 . ?
C6" H6"B 0.9900 . ?
C8" C9" 1.521(10) . ?
C8" H8"A 0.9900 . ?
C8" H8"B 0.9900 . ?

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 O1 C4 117.7(5) . . ?
C2 O8 C6 115.3(5) . . ?
C3 O15 C8 117.3(6) . . ?
C2 N1 C1 113.1(6) . . ?
C3 N2 C2 112.6(6) . . ?
C3 N3 C1 111.9(6) . . ?
O2 N4 O3 127.7(7) . . ?
O2 N4 C5 118.8(7) . . ?
O3 N4 C5 113.5(6) . . ?
O5 N5 O4 127.7(7) . . ?
O5 N5 C5 117.8(6) . . ?
O4 N5 C5 114.4(6) . . ?
O7 N6 O6 126.5(6) . . ?
O7 N6 C5 115.6(6) . . ?
O6 N6 C5 117.8(6) . . ?
O10 N7 O9 128.8(8) . . ?
O10 N7 C7 113.0(8) . . ?
O9 N7 C7 118.1(8) . . ?
O12 N8 O11 130.3(8) . . ?
O12 N8 C7 115.7(8) . . ?
O11 N8 C7 114.0(7) . . ?
O14 N9 O13 127.4(8) . . ?
O14 N9 C7 118.5(7) . . ?
O13 N9 C7 114.1(7) . . ?
O16 N10 O17 128.0(8) . . ?
O16 N10 C9 115.6(7) . . ?
O17 N10 C9 116.2(7) . . ?
O18 N11 O19 128.5(7) . . ?
O18 N11 C9 114.7(7) . . ?
O19 N11 C9 116.7(6) . . ?
O21 N12 O20 127.3(7) . . ?
O21 N12 C9 115.7(7) . . ?
O20 N12 C9 117.0(7) . . ?
N1 C1 N3 127.3(6) . . ?
N1 C1 O1 112.8(6) . . ?
N3 C1 O1 119.8(6) . . ?
N1 C2 N2 127.0(7) . . ?
N1 C2 O8 118.1(6) . . ?
N2 C2 O8 114.9(6) . . ?
N2 C3 N3 128.0(7) . . ?
N2 C3 O15 120.2(6) . . ?
N3 C3 O15 111.8(6) . . ?
O1 C4 C5 106.0(6) . . ?
O1 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
O1 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N6 C5 N5 107.3(5) . . ?
N6 C5 N4 107.3(5) . . ?
N5 C5 N4 106.7(6) . . ?
N6 C5 C4 110.2(6) . . ?
N5 C5 C4 113.1(6) . . ?
N4 C5 C4 112.0(6) . . ?
O8 C6 C7 106.4(6) . . ?
O8 C6 H6A 110.4 . . ?
C7 C6 H6A 110.4 . . ?
O8 C6 H6B 110.4 . . ?
C7 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
N7 C7 C6 112.6(7) . . ?
N7 C7 N9 107.7(7) . . ?
C6 C7 N9 108.7(7) . . ?
N7 C7 N8 110.4(7) . . ?
C6 C7 N8 112.2(7) . . ?
N9 C7 N8 104.8(7) . . ?
O15 C8 C9 104.5(6) . . ?
O15 C8 H8A 110.8 . . ?
C9 C8 H8A 110.8 . . ?
O15 C8 H8B 110.8 . . ?
C9 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
N10 C9 N11 108.6(6) . . ?
N10 C9 N12 105.0(6) . . ?
N11 C9 N12 108.0(6) . . ?
N10 C9 C8 112.3(6) . . ?
N11 C9 C8 112.4(7) . . ?
N12 C9 C8 110.2(6) . . ?
C1' O1' C4' 121.2(5) . . ?
C2' O8' C6' 114.1(6) . . ?
C3' O15' C8' 117.0(5) . . ?
C2' N1' C1' 114.4(6) . . ?
C3' N2' C2' 111.4(6) . . ?
C1' N3' C3' 112.0(6) . . ?
O3' N4' O2' 130.5(8) . . ?
O3' N4' C5' 113.3(6) . . ?
O2' N4' C5' 116.2(8) . . ?
O5' N5' O4' 126.5(8) . . ?
O5' N5' C5' 118.1(7) . . ?
O4' N5' C5' 115.2(7) . . ?
O7' N6' O6' 129.2(7) . . ?
O7' N6' C5' 114.6(7) . . ?
O6' N6' C5' 116.2(7) . . ?
O10' N7' O9' 126.3(7) . . ?
O10' N7' C7' 116.1(7) . . ?
O9' N7' C7' 117.6(7) . . ?
O11' N8' O12' 125.4(7) . . ?
O11' N8' C7' 116.2(6) . . ?
O12' N8' C7' 118.4(6) . . ?
O14' N9' O13' 126.4(6) . . ?
O14' N9' C7' 115.0(6) . . ?
O13' N9' C7' 118.6(6) . . ?
O16' N10' O17' 126.5(6) . . ?
O16' N10' C9' 115.8(6) . . ?
O17' N10' C9' 117.7(6) . . ?
O19' N11' O18' 127.4(7) . . ?
O19' N11' C9' 116.7(6) . . ?
O18' N11' C9' 115.8(6) . . ?
O21' N12' O20' 127.9(7) . . ?
O21' N12' C9' 114.7(6) . . ?
O20' N12' C9' 117.4(6) . . ?
N3' C1' N1' 126.8(7) . . ?
N3' C1' O1' 120.9(6) . . ?
N1' C1' O1' 112.2(6) . . ?
N1' C2' O8' 120.0(6) . . ?
N1' C2' N2' 127.1(6) . . ?
O8' C2' N2' 112.8(6) . . ?
N2' C3' N3' 128.2(6) . . ?
N2' C3' O15' 118.0(6) . . ?
N3' C3' O15' 113.8(6) . . ?
O1' C4' C5' 105.9(5) . . ?
O1' C4' H4'A 110.6 . . ?
C5' C4' H4'A 110.6 . . ?
O1' C4' H4'B 110.6 . . ?
C5' C4' H4'B 110.6 . . ?
H4'A C4' H4'B 108.7 . . ?
N6' C5' N5' 107.3(6) . . ?
N6' C5' C4' 112.1(6) . . ?
N5' C5' C4' 112.2(6) . . ?
N6' C5' N4' 107.5(6) . . ?
N5' C5' N4' 107.8(6) . . ?
C4' C5' N4' 109.7(6) . . ?
O8' C6' C7' 105.3(6) . . ?
O8' C6' H6'A 110.7 . . ?
C7' C6' H6'A 110.7 . . ?
O8' C6' H6'B 110.7 . . ?
C7' C6' H6'B 110.7 . . ?
H6'A C6' H6'B 108.8 . . ?
C6' C7' N7' 112.3(6) . . ?
C6' C7' N9' 111.2(6) . . ?
N7' C7' N9' 104.9(5) . . ?
C6' C7' N8' 115.1(5) . . ?
N7' C7' N8' 107.6(6) . . ?
N9' C7' N8' 105.0(5) . . ?
O15' C8' C9' 105.5(6) . . ?
O15' C8' H8'A 110.6 . . ?
C9' C8' H8'A 110.6 . . ?
O15' C8' H8'B 110.6 . . ?
C9' C8' H8'B 110.6 . . ?
H8'A C8' H8'B 108.8 . . ?
N10' C9' N11' 108.5(5) . . ?
N10' C9' N12' 109.6(6) . . ?
N11' C9' N12' 104.8(6) . . ?
N10' C9' C8' 110.8(6) . . ?
N11' C9' C8' 113.9(6) . . ?
N12' C9' C8' 108.9(6) . . ?
C1" O1" C4" 121.0(5) . . ?
C2" O8" C6" 114.8(5) . . ?
C3" O15" C8" 116.5(6) . . ?
C2" N1" C1" 112.4(6) . . ?
C3" N2" C2" 113.0(6) . . ?
C1" N3" C3" 112.3(6) . . ?
O3" N4" O2" 127.4(7) . . ?
O3" N4" C5" 115.6(6) . . ?
O2" N4" C5" 117.0(7) . . ?
O4" N5" O5" 126.6(7) . . ?
O4" N5" C5" 116.9(6) . . ?
O5" N5" C5" 116.5(7) . . ?
O6" N6" O7"A 125.4(7) . . ?
O6" N6" O7"B 126.1(8) . . ?
O7"A N6" O7"B 25.8(6) . . ?
O6" N6" C5" 119.3(6) . . ?
O7"A N6" C5" 113.9(7) . . ?
O7"B N6" C5" 112.6(8) . . ?
O9" N7" O10" 128.6(7) . . ?
O9" N7" C7" 117.2(7) . . ?
O10" N7" C7" 114.0(6) . . ?
O11" N8" O12" 128.1(7) . . ?
O11" N8" C7" 116.1(6) . . ?
O12" N8" C7" 115.7(6) . . ?
O13" N9" O14" 127.7(7) . . ?
O13" N9" C7" 117.0(6) . . ?
O14" N9" C7" 115.1(6) . . ?
O17" N10" O16" 127.0(7) . . ?
O17" N10" C9" 118.6(6) . . ?
O16" N10" C9" 114.3(6) . . ?
O19" N11" O18" 128.0(7) . . ?
O19" N11" C9" 116.5(6) . . ?
O18" N11" C9" 115.6(6) . . ?
O20" N12" O21" 128.5(6) . . ?
O20" N12" C9" 118.5(6) . . ?
O21" N12" C9" 113.0(5) . . ?
O1" C1" N3" 120.7(6) . . ?
O1" C1" N1" 112.1(6) . . ?
N3" C1" N1" 127.1(7) . . ?
N1" C2" N2" 127.5(6) . . ?
N1" C2" O8" 118.9(6) . . ?
N2" C2" O8" 113.7(6) . . ?
N2" C3" N3" 127.6(6) . . ?
N2" C3" O15" 119.1(7) . . ?
N3" C3" O15" 113.3(6) . . ?
O1" C4" C5" 106.6(5) . . ?
O1" C4" H4"A 110.4 . . ?
C5" C4" H4"A 110.4 . . ?
O1" C4" H4"B 110.4 . . ?
C5" C4" H4"B 110.4 . . ?
H4"A C4" H4"B 108.6 . . ?
N6" C5" N4" 108.0(6) . . ?
N6" C5" N5" 105.7(6) . . ?
N4" C5" N5" 109.0(6) . . ?
N6" C5" C4" 111.2(6) . . ?
N4" C5" C4" 110.1(6) . . ?
N5" C5" C4" 112.6(6) . . ?
O8" C6" C7" 105.9(5) . . ?
O8" C6" H6"A 110.6 . . ?
C7" C6" H6"A 110.6 . . ?
O8" C6" H6"B 110.6 . . ?
C7" C6" H6"B 110.6 . . ?
H6"A C6" H6"B 108.7 . . ?
N9" C7" N7" 107.0(5) . . ?
N9" C7" C6" 110.0(6) . . ?
N7" C7" C6" 111.0(6) . . ?
N9" C7" N8" 108.1(5) . . ?
N7" C7" N8" 107.4(6) . . ?
C6" C7" N8" 113.0(6) . . ?
O15" C8" C9" 108.3(5) . . ?
O15" C8" H8"A 110.0 . . ?
C9" C8" H8"A 110.0 . . ?
O15" C8" H8"B 110.0 . . ?
C9" C8" H8"B 110.0 . . ?
H8"A C8" H8"B 108.4 . . ?
N12" C9" N11" 107.9(6) . . ?
N12" C9" N10" 108.2(5) . . ?
N11" C9" N10" 107.1(5) . . ?
N12" C9" C8" 109.1(5) . . ?
N11" C9" C8" 114.0(6) . . ?
N10" C9" C8" 110.3(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N3 3.4(11) . . . . ?
C2 N1 C1 O1 -175.1(6) . . . . ?
C3 N3 C1 N1 -1.5(10) . . . . ?
C3 N3 C1 O1 176.9(6) . . . . ?
C4 O1 C1 N1 178.8(6) . . . . ?
C4 O1 C1 N3 0.2(9) . . . . ?
C1 N1 C2 N2 -2.6(11) . . . . ?
C1 N1 C2 O8 175.9(6) . . . . ?
C3 N2 C2 N1 0.0(11) . . . . ?
C3 N2 C2 O8 -178.5(6) . . . . ?
C6 O8 C2 N1 -5.9(10) . . . . ?
C6 O8 C2 N2 172.7(6) . . . . ?
C2 N2 C3 N3 2.5(11) . . . . ?
C2 N2 C3 O15 -178.5(6) . . . . ?
C1 N3 C3 N2 -1.8(11) . . . . ?
C1 N3 C3 O15 179.1(6) . . . . ?
C8 O15 C3 N2 -2.9(10) . . . . ?
C8 O15 C3 N3 176.3(6) . . . . ?
C1 O1 C4 C5 129.9(6) . . . . ?
O7 N6 C5 N5 -83.9(8) . . . . ?
O6 N6 C5 N5 95.0(7) . . . . ?
O7 N6 C5 N4 161.8(6) . . . . ?
O6 N6 C5 N4 -19.4(9) . . . . ?
O7 N6 C5 C4 39.6(9) . . . . ?
O6 N6 C5 C4 -141.6(7) . . . . ?
O5 N5 C5 N6 -17.8(9) . . . . ?
O4 N5 C5 N6 161.2(6) . . . . ?
O5 N5 C5 N4 96.9(7) . . . . ?
O4 N5 C5 N4 -84.0(7) . . . . ?
O5 N5 C5 C4 -139.5(7) . . . . ?
O4 N5 C5 C4 39.5(8) . . . . ?
O2 N4 C5 N6 107.6(7) . . . . ?
O3 N4 C5 N6 -73.7(7) . . . . ?
O2 N4 C5 N5 -7.1(9) . . . . ?
O3 N4 C5 N5 171.6(6) . . . . ?
O2 N4 C5 C4 -131.3(7) . . . . ?
O3 N4 C5 C4 47.4(8) . . . . ?
O1 C4 C5 N6 159.8(5) . . . . ?
O1 C4 C5 N5 -80.2(7) . . . . ?
O1 C4 C5 N4 40.4(7) . . . . ?
C2 O8 C6 C7 160.7(7) . . . . ?
O10 N7 C7 C6 62.6(10) . . . . ?
O9 N7 C7 C6 -114.3(10) . . . . ?
O10 N7 C7 N9 -57.3(10) . . . . ?
O9 N7 C7 N9 125.9(9) . . . . ?
O10 N7 C7 N8 -171.2(7) . . . . ?
O9 N7 C7 N8 12.0(11) . . . . ?
O8 C6 C7 N7 46.8(9) . . . . ?
O8 C6 C7 N9 166.1(6) . . . . ?
O8 C6 C7 N8 -78.5(8) . . . . ?
O14 N9 C7 N7 142.6(9) . . . . ?
O13 N9 C7 N7 -35.4(10) . . . . ?
O14 N9 C7 C6 20.3(11) . . . . ?
O13 N9 C7 C6 -157.7(8) . . . . ?
O14 N9 C7 N8 -99.8(9) . . . . ?
O13 N9 C7 N8 82.2(9) . . . . ?
O12 N8 C7 N7 106.4(8) . . . . ?
O11 N8 C7 N7 -74.6(9) . . . . ?
O12 N8 C7 C6 -127.1(8) . . . . ?
O11 N8 C7 C6 51.9(10) . . . . ?
O12 N8 C7 N9 -9.3(10) . . . . ?
O11 N8 C7 N9 169.7(7) . . . . ?
C3 O15 C8 C9 -131.8(7) . . . . ?
O16 N10 C9 N11 -170.8(7) . . . . ?
O17 N10 C9 N11 12.2(9) . . . . ?
O16 N10 C9 N12 73.9(8) . . . . ?
O17 N10 C9 N12 -103.2(8) . . . . ?
O16 N10 C9 C8 -45.8(9) . . . . ?
O17 N10 C9 C8 137.1(8) . . . . ?
O18 N11 C9 N10 74.9(9) . . . . ?
O19 N11 C9 N10 -108.8(8) . . . . ?
O18 N11 C9 N12 -171.8(8) . . . . ?
O19 N11 C9 N12 4.5(9) . . . . ?
O18 N11 C9 C8 -50.1(10) . . . . ?
O19 N11 C9 C8 126.3(7) . . . . ?
O21 N12 C9 N10 -155.9(7) . . . . ?
O20 N12 C9 N10 24.9(9) . . . . ?
O21 N12 C9 N11 88.4(8) . . . . ?
O20 N12 C9 N11 -90.8(8) . . . . ?
O21 N12 C9 C8 -34.8(10) . . . . ?
O20 N12 C9 C8 146.0(7) . . . . ?
O15 C8 C9 N10 -45.8(8) . . . . ?
O15 C8 C9 N11 77.0(8) . . . . ?
O15 C8 C9 N12 -162.4(6) . . . . ?
C3' N3' C1' N1' 1.6(10) . . . . ?
C3' N3' C1' O1' 179.0(6) . . . . ?
C2' N1' C1' N3' -3.3(10) . . . . ?
C2' N1' C1' O1' 179.1(6) . . . . ?
C4' O1' C1' N3' 9.0(10) . . . . ?
C4' O1' C1' N1' -173.2(6) . . . . ?
C1' N1' C2' O8' -179.0(6) . . . . ?
C1' N1' C2' N2' 1.8(10) . . . . ?
C6' O8' C2' N1' -0.1(9) . . . . ?
C6' O8' C2' N2' 179.2(6) . . . . ?
C3' N2' C2' N1' 1.0(10) . . . . ?
C3' N2' C2' O8' -178.2(6) . . . . ?
C2' N2' C3' N3' -3.0(10) . . . . ?
C2' N2' C3' O15' 176.9(6) . . . . ?
C1' N3' C3' N2' 1.9(10) . . . . ?
C1' N3' C3' O15' -178.1(6) . . . . ?
C8' O15' C3' N2' -0.3(9) . . . . ?
C8' O15' C3' N3' 179.7(6) . . . . ?
C1' O1' C4' C5' 117.5(7) . . . . ?
O7' N6' C5' N5' -83.7(9) . . . . ?
O6' N6' C5' N5' 94.1(8) . . . . ?
O7' N6' C5' C4' 40.0(9) . . . . ?
O6' N6' C5' C4' -142.2(7) . . . . ?
O7' N6' C5' N4' 160.6(7) . . . . ?
O6' N6' C5' N4' -21.6(9) . . . . ?
O5' N5' C5' N6' -18.3(11) . . . . ?
O4' N5' C5' N6' 157.1(8) . . . . ?
O5' N5' C5' C4' -141.9(9) . . . . ?
O4' N5' C5' C4' 33.5(11) . . . . ?
O5' N5' C5' N4' 97.2(10) . . . . ?
O4' N5' C5' N4' -87.3(9) . . . . ?
O1' C4' C5' N6' 155.9(6) . . . . ?
O1' C4' C5' N5' -83.2(7) . . . . ?
O1' C4' C5' N4' 36.5(8) . . . . ?
O3' N4' C5' N6' -70.3(8) . . . . ?
O2' N4' C5' N6' 110.4(8) . . . . ?
O3' N4' C5' N5' 174.3(7) . . . . ?
O2' N4' C5' N5' -5.0(9) . . . . ?
O3' N4' C5' C4' 51.9(9) . . . . ?
O2' N4' C5' C4' -127.4(7) . . . . ?
C2' O8' C6' C7' 161.4(6) . . . . ?
O8' C6' C7' N7' -50.0(7) . . . . ?
O8' C6' C7' N9' -167.2(5) . . . . ?
O8' C6' C7' N8' 73.6(7) . . . . ?
O10' N7' C7' C6' -37.4(8) . . . . ?
O9' N7' C7' C6' 140.8(7) . . . . ?
O10' N7' C7' N9' 83.5(7) . . . . ?
O9' N7' C7' N9' -98.3(7) . . . . ?
O10' N7' C7' N8' -165.0(6) . . . . ?
O9' N7' C7' N8' 13.2(8) . . . . ?
O14' N9' C7' C6' -44.1(8) . . . . ?
O13' N9' C7' C6' 137.8(7) . . . . ?
O14' N9' C7' N7' -165.7(6) . . . . ?
O13' N9' C7' N7' 16.2(9) . . . . ?
O14' N9' C7' N8' 81.0(7) . . . . ?
O13' N9' C7' N8' -97.2(7) . . . . ?
O11' N8' C7' C6' -42.5(8) . . . . ?
O12' N8' C7' C6' 137.6(7) . . . . ?
O11' N8' C7' N7' 83.5(7) . . . . ?
O12' N8' C7' N7' -96.4(8) . . . . ?
O11' N8' C7' N9' -165.1(6) . . . . ?
O12' N8' C7' N9' 15.0(9) . . . . ?
C3' O15' C8' C9' -145.6(6) . . . . ?
O16' N10' C9' N11' -174.6(6) . . . . ?
O17' N10' C9' N11' 4.2(8) . . . . ?
O16' N10' C9' N12' 71.4(7) . . . . ?
O17' N10' C9' N12' -109.8(7) . . . . ?
O16' N10' C9' C8' -48.8(8) . . . . ?
O17' N10' C9' C8' 130.0(7) . . . . ?
O19' N11' C9' N10' -89.8(8) . . . . ?
O18' N11' C9' N10' 87.1(8) . . . . ?
O19' N11' C9' N12' 27.2(8) . . . . ?
O18' N11' C9' N12' -155.9(6) . . . . ?
O19' N11' C9' C8' 146.2(7) . . . . ?
O18' N11' C9' C8' -36.9(9) . . . . ?
O21' N12' C9' N10' -170.7(6) . . . . ?
O20' N12' C9' N10' 9.2(8) . . . . ?
O21' N12' C9' N11' 73.0(7) . . . . ?
O20' N12' C9' N11' -107.1(7) . . . . ?
O21' N12' C9' C8' -49.3(8) . . . . ?
O20' N12' C9' C8' 130.6(7) . . . . ?
O15' C8' C9' N10' -42.2(8) . . . . ?
O15' C8' C9' N11' 80.5(7) . . . . ?
O15' C8' C9' N12' -162.9(6) . . . . ?
C4" O1" C1" N3" 11.5(9) . . . . ?
C4" O1" C1" N1" -171.3(6) . . . . ?
C3" N3" C1" O1" 178.6(6) . . . . ?
C3" N3" C1" N1" 2.0(10) . . . . ?
C2" N1" C1" O1" -179.5(6) . . . . ?
C2" N1" C1" N3" -2.6(10) . . . . ?
C1" N1" C2" N2" 0.7(10) . . . . ?
C1" N1" C2" O8" -179.8(6) . . . . ?
C3" N2" C2" N1" 1.5(10) . . . . ?
C3" N2" C2" O8" -178.0(6) . . . . ?
C6" O8" C2" N1" 0.6(8) . . . . ?
C6" O8" C2" N2" -179.8(6) . . . . ?
C2" N2" C3" N3" -2.3(10) . . . . ?
C2" N2" C3" O15" 177.7(6) . . . . ?
C1" N3" C3" N2" 0.8(10) . . . . ?
C1" N3" C3" O15" -179.3(6) . . . . ?
C8" O15" C3" N2" -1.3(9) . . . . ?
C8" O15" C3" N3" 178.8(6) . . . . ?
C1" O1" C4" C5" 113.7(7) . . . . ?
O6" N6" C5" N4" -19.7(10) . . . . ?
O7"A N6" C5" N4" 147.4(8) . . . . ?
O7"B N6" C5" N4" 175.6(9) . . . . ?
O6" N6" C5" N5" 96.9(8) . . . . ?
O7"A N6" C5" N5" -96.0(9) . . . . ?
O7"B N6" C5" N5" -67.9(10) . . . . ?
O6" N6" C5" C4" -140.6(7) . . . . ?
O7"A N6" C5" C4" 26.4(11) . . . . ?
O7"B N6" C5" C4" 54.6(10) . . . . ?
O3" N4" C5" N6" -65.1(8) . . . . ?
O2" N4" C5" N6" 117.3(7) . . . . ?
O3" N4" C5" N5" -179.4(6) . . . . ?
O2" N4" C5" N5" 2.9(9) . . . . ?
O3" N4" C5" C4" 56.6(8) . . . . ?
O2" N4" C5" C4" -121.1(7) . . . . ?
O4" N5" C5" N6" 152.4(7) . . . . ?
O5" N5" C5" N6" -29.9(9) . . . . ?
O4" N5" C5" N4" -91.8(8) . . . . ?
O5" N5" C5" N4" 86.0(8) . . . . ?
O4" N5" C5" C4" 30.8(10) . . . . ?
O5" N5" C5" C4" -151.5(7) . . . . ?
O1" C4" C5" N6" 161.3(6) . . . . ?
O1" C4" C5" N4" 41.6(8) . . . . ?
O1" C4" C5" N5" -80.3(7) . . . . ?
C2" O8" C6" C7" 162.7(6) . . . . ?
O13" N9" C7" N7" 23.8(9) . . . . ?
O14" N9" C7" N7" -161.3(6) . . . . ?
O13" N9" C7" C6" 144.5(7) . . . . ?
O14" N9" C7" C6" -40.6(8) . . . . ?
O13" N9" C7" N8" -91.7(8) . . . . ?
O14" N9" C7" N8" 83.2(7) . . . . ?
O9" N7" C7" N9" -96.3(8) . . . . ?
O10" N7" C7" N9" 79.3(7) . . . . ?
O9" N7" C7" C6" 143.7(7) . . . . ?
O10" N7" C7" C6" -40.7(8) . . . . ?
O9" N7" C7" N8" 19.7(8) . . . . ?
O10" N7" C7" N8" -164.8(6) . . . . ?
O8" C6" C7" N9" -168.5(5) . . . . ?
O8" C6" C7" N7" -50.2(7) . . . . ?
O8" C6" C7" N8" 70.6(7) . . . . ?
O11" N8" C7" N9" -176.2(6) . . . . ?
O12" N8" C7" N9" 1.3(8) . . . . ?
O11" N8" C7" N7" 68.7(8) . . . . ?
O12" N8" C7" N7" -113.9(7) . . . . ?
O11" N8" C7" C6" -54.2(8) . . . . ?
O12" N8" C7" C6" 123.3(7) . . . . ?
C3" O15" C8" C9" -143.2(6) . . . . ?
O20" N12" C9" N11" -102.3(7) . . . . ?
O21" N12" C9" N11" 76.0(7) . . . . ?
O20" N12" C9" N10" 13.3(8) . . . . ?
O21" N12" C9" N10" -168.5(6) . . . . ?
O20" N12" C9" C8" 133.4(7) . . . . ?
O21" N12" C9" C8" -48.4(8) . . . . ?
O19" N11" C9" N12" 23.9(8) . . . . ?
O18" N11" C9" N12" -156.0(6) . . . . ?
O19" N11" C9" N10" -92.3(7) . . . . ?
O18" N11" C9" N10" 87.8(7) . . . . ?
O19" N11" C9" C8" 145.3(7) . . . . ?
O18" N11" C9" C8" -34.6(9) . . . . ?
O17" N10" C9" N12" -112.8(7) . . . . ?
O16" N10" C9" N12" 71.0(7) . . . . ?
O17" N10" C9" N11" 3.2(9) . . . . ?
O16" N10" C9" N11" -172.9(6) . . . . ?
O17" N10" C9" C8" 127.9(7) . . . . ?
O16" N10" C9" C8" -48.3(8) . . . . ?
O15" C8" C9" N12" -161.3(6) . . . . ?
O15" C8" C9" N11" 78.0(8) . . . . ?
O15" C8" C9" N10" -42.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.20
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_comp21
_database_code_depnum_ccdc_archive 'CCDC 1434739'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 N10 O14'
_chemical_formula_sum            'C7 H6 N10 O14'
_chemical_formula_weight         454.22

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0315(5)
_cell_length_b                   11.7427(10)
_cell_length_c                   11.9923(10)
_cell_angle_alpha                101.500(2)
_cell_angle_beta                 101.738(2)
_cell_angle_gamma                97.607(2)
_cell_volume                     801.56(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3634
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      31.87

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14710
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3862
_reflns_number_gt                2834
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'

_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)+(0.0574P)²+0.3145P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3862
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.8189(3) 1.12102(14) 0.18629(14) 0.0201(4) Uani 1 1 d . A .
O2 O 0.3589(3) 1.16490(19) -0.03064(16) 0.0424(5) Uani 1 1 d . . .
O3 O 0.4883(3) 1.27551(16) 0.14412(16) 0.0291(4) Uani 1 1 d . . .
O4 O 0.847(3) 1.0449(5) -0.0366(9) 0.041(3) Uani 0.48(3) 1 d P A 1
O4' O 0.698(3) 1.0313(5) -0.0619(5) 0.044(3) Uani 0.52(3) 1 d P A 2
O5 O 0.7603(4) 1.15986(18) -0.15674(15) 0.0397(5) Uani 1 1 d . A .
O6 O 0.6663(3) 1.38739(16) -0.03867(17) 0.0327(5) Uani 1 1 d . A .
O7 O 1.0278(3) 1.38005(15) 0.02754(16) 0.0282(4) Uani 1 1 d . A .
O8 O 0.9416(3) 0.83284(13) 0.38189(13) 0.0166(3) Uani 1 1 d . . .
O9 O 0.6045(3) 0.61973(14) 0.52906(14) 0.0249(4) Uani 1 1 d . . .
O10 O 0.9588(3) 0.67786(15) 0.52183(14) 0.0250(4) Uani 1 1 d . . .
O11 O 0.8049(3) 0.58957(18) 0.18687(15) 0.0336(5) Uani 1 1 d . . .
O12 O 0.8570(3) 0.49237(15) 0.32377(16) 0.0289(4) Uani 1 1 d . . .
O13 O 0.3660(3) 0.49750(14) 0.26513(14) 0.0239(4) Uani 1 1 d . . .
O14 O 0.2868(3) 0.66994(15) 0.33180(16) 0.0281(4) Uani 1 1 d . . .
N1 N 0.8640(3) 0.97632(16) 0.28127(15) 0.0150(4) Uani 1 1 d . . .
N2 N 1.2316(3) 0.98066(16) 0.40471(15) 0.0153(4) Uani 1 1 d . . .
N3 N 1.1793(3) 1.12957(15) 0.29640(15) 0.0143(4) Uani 1 1 d . . .
N4 N 0.5110(3) 1.22054(16) 0.05168(16) 0.0179(4) Uani 1 1 d . . .
N5 N 0.7611(4) 1.13249(19) -0.06629(18) 0.0302(5) Uani 1 1 d . . .
N6 N 0.8242(3) 1.34457(17) 0.00766(17) 0.0194(4) Uani 1 1 d . . .
N7 N 0.7530(3) 0.64995(16) 0.48026(16) 0.0177(4) Uani 1 1 d . . .
N8 N 0.7942(3) 0.57219(18) 0.28169(17) 0.0210(4) Uani 1 1 d . . .
N9 N 0.4165(3) 0.60203(16) 0.31186(16) 0.0174(4) Uani 1 1 d . . .
N10 N 1.5274(3) 1.13127(18) 0.41766(17) 0.0174(4) Uani 1 1 d . . .
C1 C 0.9646(4) 1.07466(19) 0.25838(17) 0.0140(4) Uani 1 1 d . . .
C2 C 1.0137(4) 0.93529(18) 0.35329(17) 0.0138(4) Uani 1 1 d . . .
C3 C 1.3103(4) 1.07873(18) 0.37133(17) 0.0141(4) Uani 1 1 d . . .
C4 C 0.9216(4) 1.2210(2) 0.15109(19) 0.0182(5) Uani 1 1 d . . .
H4A H 1.0741 1.2104 0.1364 0.022 Uiso 1 1 calc R A .
H4B H 0.9416 1.2941 0.2127 0.022 Uiso 1 1 calc R . .
C5 C 0.7585(4) 1.22799(18) 0.04034(18) 0.0149(4) Uani 1 1 d . A .
C6 C 0.7061(4) 0.78081(19) 0.33302(19) 0.0162(4) Uani 1 1 d . . .
H6A H 0.6653 0.7786 0.2483 0.019 Uiso 1 1 calc R . .
H6B H 0.6061 0.8274 0.3719 0.019 Uiso 1 1 calc R . .
C7 C 0.6734(4) 0.65640(19) 0.35210(18) 0.0147(4) Uani 1 1 d . . .
H1 H 1.581(5) 1.194(3) 0.396(2) 0.028(7) Uiso 1 1 d . . .
H2 H 1.613(5) 1.101(2) 0.466(3) 0.032(8) Uiso 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 C1 1.350(2) . ?
O1 C4 1.433(3) . ?
O2 N4 1.208(2) . ?
O3 N4 1.210(2) . ?
O4 N5 1.289(10) . ?
O4' N5 1.213(8) . ?
O5 N5 1.191(3) . ?
O6 N6 1.221(2) . ?
O7 N6 1.202(2) . ?
O8 C2 1.357(3) . ?
O8 C6 1.422(3) . ?
O9 N7 1.218(3) . ?
O10 N7 1.213(2) . ?
O11 N8 1.207(3) . ?
O12 N8 1.217(3) . ?
O13 N9 1.213(2) . ?
O14 N9 1.213(2) . ?
N1 C2 1.325(3) . ?
N1 C1 1.336(3) . ?
N2 C2 1.321(3) . ?
N2 C3 1.352(3) . ?
N3 C1 1.312(3) . ?
N3 C3 1.356(3) . ?
N4 C5 1.519(3) . ?
N5 C5 1.528(3) . ?
N6 C5 1.523(3) . ?
N7 C7 1.534(3) . ?
N8 C7 1.526(3) . ?
N9 C7 1.533(3) . ?
N10 C3 1.326(3) . ?
N10 H1 0.87(3) . ?
N10 H2 0.86(3) . ?
C4 C5 1.507(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.517(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 O1 C4 115.51(17) . . ?
C2 O8 C6 115.76(16) . . ?
C2 N1 C1 110.71(18) . . ?
C2 N2 C3 113.24(18) . . ?
C1 N3 C3 113.57(18) . . ?
O2 N4 O3 126.7(2) . . ?
O2 N4 C5 118.6(2) . . ?
O3 N4 C5 114.66(17) . . ?
O5 N5 O4' 122.0(3) . . ?
O5 N5 O4 124.6(3) . . ?
O4' N5 O4 40.3(3) . . ?
O5 N5 C5 118.5(2) . . ?
O4' N5 C5 116.1(3) . . ?
O4 N5 C5 111.9(4) . . ?
O7 N6 O6 128.54(19) . . ?
O7 N6 C5 114.73(17) . . ?
O6 N6 C5 116.67(18) . . ?
O10 N7 O9 127.5(2) . . ?
O10 N7 C7 115.45(18) . . ?
O9 N7 C7 117.06(18) . . ?
O11 N8 O12 127.5(2) . . ?
O11 N8 C7 115.18(19) . . ?
O12 N8 C7 117.18(19) . . ?
O14 N9 O13 127.56(19) . . ?
O14 N9 C7 115.16(18) . . ?
O13 N9 C7 117.28(17) . . ?
C3 N10 H1 119.1(19) . . ?
C3 N10 H2 119(2) . . ?
H1 N10 H2 122(3) . . ?
N3 C1 N1 128.93(18) . . ?
N3 C1 O1 117.91(19) . . ?
N1 C1 O1 113.16(18) . . ?
N2 C2 N1 129.2(2) . . ?
N2 C2 O8 112.51(17) . . ?
N1 C2 O8 118.32(19) . . ?
N10 C3 N2 118.15(19) . . ?
N10 C3 N3 117.5(2) . . ?
N2 C3 N3 124.26(19) . . ?
O1 C4 C5 105.96(17) . . ?
O1 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
O1 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 N4 112.72(17) . . ?
C4 C5 N6 110.78(17) . . ?
N4 C5 N6 106.68(16) . . ?
C4 C5 N5 113.46(18) . . ?
N4 C5 N5 107.60(17) . . ?
N6 C5 N5 105.10(17) . . ?
O8 C6 C7 107.48(16) . . ?
O8 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
O8 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C6 C7 N8 114.32(18) . . ?
C6 C7 N9 108.90(16) . . ?
N8 C7 N9 105.58(16) . . ?
C6 C7 N7 114.06(17) . . ?
N8 C7 N7 106.30(16) . . ?
N9 C7 N7 107.13(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C1 N1 -1.9(3) . . . . ?
C3 N3 C1 O1 177.85(18) . . . . ?
C2 N1 C1 N3 0.4(3) . . . . ?
C2 N1 C1 O1 -179.29(17) . . . . ?
C4 O1 C1 N3 5.1(3) . . . . ?
C4 O1 C1 N1 -175.08(18) . . . . ?
C3 N2 C2 N1 -4.4(3) . . . . ?
C3 N2 C2 O8 176.03(17) . . . . ?
C1 N1 C2 N2 3.1(3) . . . . ?
C1 N1 C2 O8 -177.41(18) . . . . ?
C6 O8 C2 N2 177.89(18) . . . . ?
C6 O8 C2 N1 -1.7(3) . . . . ?
C2 N2 C3 N10 -179.92(19) . . . . ?
C2 N2 C3 N3 2.5(3) . . . . ?
C1 N3 C3 N10 -177.37(19) . . . . ?
C1 N3 C3 N2 0.2(3) . . . . ?
C1 O1 C4 C5 158.73(17) . . . . ?
O1 C4 C5 N4 49.2(2) . . . . ?
O1 C4 C5 N6 168.61(16) . . . . ?
O1 C4 C5 N5 -73.5(2) . . . . ?
O2 N4 C5 C4 -141.0(2) . . . . ?
O3 N4 C5 C4 40.9(2) . . . . ?
O2 N4 C5 N6 97.2(2) . . . . ?
O3 N4 C5 N6 -80.9(2) . . . . ?
O2 N4 C5 N5 -15.2(3) . . . . ?
O3 N4 C5 N5 166.76(18) . . . . ?
O7 N6 C5 C4 36.7(3) . . . . ?
O6 N6 C5 C4 -145.8(2) . . . . ?
O7 N6 C5 N4 159.76(18) . . . . ?
O6 N6 C5 N4 -22.8(3) . . . . ?
O7 N6 C5 N5 -86.2(2) . . . . ?
O6 N6 C5 N5 91.2(2) . . . . ?
O5 N5 C5 C4 -136.9(2) . . . . ?
O4' N5 C5 C4 63.4(10) . . . . ?
O4 N5 C5 C4 19.3(9) . . . . ?
O5 N5 C5 N4 97.6(3) . . . . ?
O4' N5 C5 N4 -62.0(10) . . . . ?
O4 N5 C5 N4 -106.1(8) . . . . ?
O5 N5 C5 N6 -15.8(3) . . . . ?
O4' N5 C5 N6 -175.4(10) . . . . ?
O4 N5 C5 N6 140.5(8) . . . . ?
C2 O8 C6 C7 167.59(17) . . . . ?
O8 C6 C7 N8 -68.0(2) . . . . ?
O8 C6 C7 N9 174.23(16) . . . . ?
O8 C6 C7 N7 54.6(2) . . . . ?
O11 N8 C7 C6 -33.2(3) . . . . ?
O12 N8 C7 C6 150.60(19) . . . . ?
O11 N8 C7 N9 86.4(2) . . . . ?
O12 N8 C7 N9 -89.7(2) . . . . ?
O11 N8 C7 N7 -159.98(19) . . . . ?
O12 N8 C7 N7 23.8(2) . . . . ?
O14 N9 C7 C6 -36.9(2) . . . . ?
O13 N9 C7 C6 143.63(19) . . . . ?
O14 N9 C7 N8 -160.06(19) . . . . ?
O13 N9 C7 N8 20.4(2) . . . . ?
O14 N9 C7 N7 86.9(2) . . . . ?
O13 N9 C7 N7 -92.6(2) . . . . ?
O10 N7 C7 C6 -67.1(2) . . . . ?
O9 N7 C7 C6 111.7(2) . . . . ?
O10 N7 C7 N8 59.8(2) . . . . ?
O9 N7 C7 N8 -121.36(19) . . . . ?
O10 N7 C7 N9 172.35(17) . . . . ?
O9 N7 C7 N9 -8.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_comp20
_database_code_depnum_ccdc_archive 'CCDC 1434740'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 N6 O9'
_chemical_formula_sum            'C5 H4 N6 O9'
_chemical_formula_weight         292.14

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   'P 21/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                   13.2903(13)
_cell_length_b                   6.6865(7)
_cell_length_c                   11.6787(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.175(2)
_cell_angle_gamma                90.00
_cell_volume                     1036.24(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6518
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      30.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15138
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         26.99
_reflns_number_total             2234
_reflns_number_gt                1803
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'

_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)+(0.0259P)²+1.1835P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2234
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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
O1 O 0.29797(11) 0.0614(2) 0.30577(11) 0.0136(3) Uani 1 1 d . . .
O2 O 0.16064(12) 0.1691(2) 0.49365(13) 0.0231(4) Uani 1 1 d . . .
O3 O 0.25014(12) -0.0878(2) 0.55160(13) 0.0243(4) Uani 1 1 d . . .
O4 O 0.08973(13) 0.0754(3) 0.22804(14) 0.0310(4) Uani 1 1 d . . .
O5 O -0.00507(12) -0.0172(3) 0.36446(14) 0.0350(5) Uani 1 1 d . . .
O6 O 0.08639(15) -0.3400(3) 0.50015(15) 0.0363(5) Uani 1 1 d . . .
O7 O 0.14191(13) -0.4535(2) 0.34052(14) 0.0241(4) Uani 1 1 d . . .
O8 O 0.47489(11) 0.5483(2) 0.14617(11) 0.0151(3) Uani 1 1 d . . .
O9 O 0.38079(11) 0.0049(2) -0.06699(11) 0.0149(3) Uani 1 1 d . . .
N1 N 0.37931(13) 0.3064(3) 0.22246(14) 0.0111(4) Uani 1 1 d . . .
H1 H 0.3835(18) 0.363(4) 0.288(2) 0.019(6) Uiso 1 1 d . . .
N2 N 0.42654(13) 0.2777(3) 0.03718(14) 0.0125(4) Uani 1 1 d . . .
H2 H 0.4589(19) 0.321(4) -0.020(2) 0.024(7) Uiso 1 1 d . . .
N3 N 0.33666(13) 0.0129(3) 0.11868(14) 0.0125(4) Uani 1 1 d . . .
N4 N 0.19176(13) -0.0004(3) 0.48559(14) 0.0146(4) Uani 1 1 d . . .
N5 N 0.07370(14) -0.0100(3) 0.31708(15) 0.0192(4) Uani 1 1 d . . .
N6 N 0.12701(14) -0.3237(3) 0.41062(15) 0.0192(4) Uani 1 1 d . . .
C1 C 0.33820(14) 0.1228(3) 0.20951(16) 0.0112(4) Uani 1 1 d . . .
C2 C 0.43033(15) 0.3893(3) 0.13524(16) 0.0116(4) Uani 1 1 d . . .
C3 C 0.38062(15) 0.0926(3) 0.02549(16) 0.0116(4) Uani 1 1 d . . .
C4 C 0.25312(16) -0.1348(3) 0.30419(17) 0.0145(4) Uani 1 1 d . . .
H4A H 0.3014 -0.2351 0.3369 0.017 Uiso 1 1 calc R . .
H4B H 0.2320 -0.1747 0.2248 0.017 Uiso 1 1 calc R . .
C5 C 0.16287(16) -0.1170(3) 0.37683(17) 0.0140(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 C1 1.336(2) . ?
O1 C4 1.440(2) . ?
O2 N4 1.212(2) . ?
O3 N4 1.213(2) . ?
O4 N5 1.216(2) . ?
O5 N5 1.212(2) . ?
O6 N6 1.208(2) . ?
O7 N6 1.217(2) . ?
O8 C2 1.220(2) . ?
O9 C3 1.229(2) . ?
N1 C1 1.349(3) . ?
N1 C2 1.371(3) . ?
N1 H1 0.85(3) . ?
N2 C2 1.365(3) . ?
N2 C3 1.383(3) . ?
N2 H2 0.86(3) . ?
N3 C1 1.289(3) . ?
N3 C3 1.371(3) . ?
N4 C5 1.521(3) . ?
N5 C5 1.520(3) . ?
N6 C5 1.521(3) . ?
C4 C5 1.512(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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 O1 C4 116.98(15) . . ?
C1 N1 C2 119.90(17) . . ?
C1 N1 H1 120.8(17) . . ?
C2 N1 H1 118.4(17) . . ?
C2 N2 C3 124.55(17) . . ?
C2 N2 H2 117.8(17) . . ?
C3 N2 H2 117.5(17) . . ?
C1 N3 C3 116.34(18) . . ?
O2 N4 O3 127.61(18) . . ?
O2 N4 C5 118.21(17) . . ?
O3 N4 C5 113.99(17) . . ?
O5 N5 O4 127.3(2) . . ?
O5 N5 C5 116.29(18) . . ?
O4 N5 C5 116.40(18) . . ?
O6 N6 O7 127.99(19) . . ?
O6 N6 C5 117.87(18) . . ?
O7 N6 C5 114.12(16) . . ?
N3 C1 O1 121.90(18) . . ?
N3 C1 N1 126.76(18) . . ?
O1 C1 N1 111.33(17) . . ?
O8 C2 N2 123.98(18) . . ?
O8 C2 N1 122.11(18) . . ?
N2 C2 N1 113.91(17) . . ?
O9 C3 N3 122.25(18) . . ?
O9 C3 N2 119.43(18) . . ?
N3 C3 N2 118.32(17) . . ?
O1 C4 C5 105.19(16) . . ?
O1 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
O1 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C4 C5 N5 113.69(17) . . ?
C4 C5 N6 110.12(17) . . ?
N5 C5 N6 107.41(16) . . ?
C4 C5 N4 109.72(16) . . ?
N5 C5 N4 107.23(16) . . ?
N6 C5 N4 108.50(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C1 O1 -179.87(17) . . . . ?
C3 N3 C1 N1 -0.7(3) . . . . ?
C4 O1 C1 N3 0.5(3) . . . . ?
C4 O1 C1 N1 -178.84(16) . . . . ?
C2 N1 C1 N3 -3.6(3) . . . . ?
C2 N1 C1 O1 175.63(16) . . . . ?
C3 N2 C2 O8 176.61(19) . . . . ?
C3 N2 C2 N1 -3.2(3) . . . . ?
C1 N1 C2 O8 -174.57(18) . . . . ?
C1 N1 C2 N2 5.2(3) . . . . ?
C1 N3 C3 O9 -177.50(19) . . . . ?
C1 N3 C3 N2 2.8(3) . . . . ?
C2 N2 C3 O9 179.47(18) . . . . ?
C2 N2 C3 N3 -0.9(3) . . . . ?
C1 O1 C4 C5 -144.06(16) . . . . ?
O1 C4 C5 N5 75.8(2) . . . . ?
O1 C4 C5 N6 -163.59(15) . . . . ?
O1 C4 C5 N4 -44.2(2) . . . . ?
O5 N5 C5 C4 169.59(19) . . . . ?
O4 N5 C5 C4 -11.4(3) . . . . ?
O5 N5 C5 N6 47.5(2) . . . . ?
O4 N5 C5 N6 -133.47(19) . . . . ?
O5 N5 C5 N4 -68.9(2) . . . . ?
O4 N5 C5 N4 110.1(2) . . . . ?
O6 N6 C5 C4 150.80(19) . . . . ?
O7 N6 C5 C4 -30.6(2) . . . . ?
O6 N6 C5 N5 -84.9(2) . . . . ?
O7 N6 C5 N5 93.7(2) . . . . ?
O6 N6 C5 N4 30.7(3) . . . . ?
O7 N6 C5 N4 -150.68(18) . . . . ?
O2 N4 C5 C4 107.0(2) . . . . ?
O3 N4 C5 C4 -68.3(2) . . . . ?
O2 N4 C5 N5 -16.9(2) . . . . ?
O3 N4 C5 N5 167.76(16) . . . . ?
O2 N4 C5 N6 -132.68(18) . . . . ?
O3 N4 C5 N6 52.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.060

