# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_exp_4290
_database_code_depnum_ccdc_archive 'CCDC 1489507'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_audit_creation_date             2016-06-29
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.5(C8 H12 K2 N18 O12)'
_chemical_formula_sum            'C4 H6 K N9 O6'
_chemical_formula_weight         315.28
_chemical_melting_point          ?
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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.0656(18)
_cell_length_b                   6.8365(8)
_cell_length_c                   19.3505(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.333(9)
_cell_angle_gamma                90.00
_cell_volume                     2253.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3059
_cell_measurement_temperature    105.5
_cell_measurement_theta_max      29.2332
_cell_measurement_theta_min      3.1545
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10970
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_temperature      105.5
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.8148   37.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -30.00   -3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.8148   65.0000  152.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   18.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.8148 -115.0000  -41.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   47.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9711  -37.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  5 omega  -48.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9711  -77.0000  150.0000 99
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0064953000
_diffrn_orient_matrix_UB_12      0.1021224000
_diffrn_orient_matrix_UB_13      -0.0025987000
_diffrn_orient_matrix_UB_21      -0.0258562000
_diffrn_orient_matrix_UB_22      -0.0057429000
_diffrn_orient_matrix_UB_23      0.0272978000
_diffrn_orient_matrix_UB_31      0.0320190000
_diffrn_orient_matrix_UB_32      0.0175059000
_diffrn_orient_matrix_UB_33      0.0243756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3225
_reflns_number_total             4426
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4426
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+12.1590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2002
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
K1 K 0.64670(7) 0.7112(2) 0.03879(5) 0.0237(3) Uani 1 1 d . . .
O2 O 0.8188(2) 0.5785(7) 0.05987(18) 0.0266(10) Uani 1 1 d . A .
N18 N 1.0946(2) 0.9571(8) -0.1706(2) 0.0194(11) Uani 1 1 d . . .
N11 N 0.8753(3) 1.0492(8) -0.3826(2) 0.0224(11) Uani 1 1 d . . .
O5 O 0.9307(2) 1.1102(7) -0.41589(17) 0.0261(10) Uani 1 1 d . . .
N15 N 1.0052(2) 0.8389(8) -0.1017(2) 0.0197(11) Uani 1 1 d . A .
N5 N 0.9437(2) 0.4811(8) 0.2661(2) 0.0171(10) Uani 1 1 d . . .
O1 O 0.9413(2) 0.6672(7) 0.06481(18) 0.0260(10) Uani 1 1 d . A .
N10 N 1.0377(2) 1.0578(8) -0.3052(2) 0.0194(11) Uani 1 1 d . . .
H10A H 1.0797 1.0535 -0.2784 0.023 Uiso 1 1 calc R . .
H10B H 1.0398 1.1001 -0.3469 0.023 Uiso 1 1 calc R . .
N7 N 1.0410(3) 0.3748(8) 0.4246(2) 0.0233(12) Uani 1 1 d . . .
O4 O 0.7174(2) 0.3425(7) 0.2281(2) 0.0258(10) Uani 1 1 d . . .
O3 O 0.7164(2) 0.5958(7) 0.16037(18) 0.0251(10) Uani 1 1 d . . .
N4 N 0.8648(2) 0.4424(8) 0.2697(2) 0.0194(11) Uani 1 1 d . . .
O6 O 0.8066(2) 1.0422(8) -0.40778(19) 0.0309(11) Uani 1 1 d . . .
N13 N 0.8860(2) 0.8796(7) -0.2048(2) 0.0182(10) Uani 1 1 d . A .
C7 C 0.8464(3) 0.9175(9) -0.2628(2) 0.0163(11) Uani 1 1 d . A .
N14 N 0.9619(2) 0.9303(8) -0.2168(2) 0.0160(10) Uani 1 1 d . . .
N12 N 0.7634(3) 0.8735(9) -0.2631(2) 0.0289(10) Uani 1 1 d U . .
N17 N 1.1292(3) 0.9102(8) -0.1083(2) 0.0206(11) Uani 1 1 d . . .
N1 N 1.0352(2) 0.5984(7) 0.1881(2) 0.0192(11) Uani 1 1 d . . .
H1A H 1.0730 0.5859 0.2191 0.023 Uiso 1 1 calc R . .
H1B H 1.0443 0.6416 0.1476 0.023 Uiso 1 1 calc R . .
N3 N 0.7500(2) 0.4706(8) 0.1974(2) 0.0192(11) Uani 1 1 d . . .
N2 N 0.8828(3) 0.6029(8) 0.0923(2) 0.0204(11) Uani 1 1 d . A .
N6 N 0.9725(2) 0.3778(8) 0.3845(2) 0.0202(11) Uani 1 1 d . . .
N16 N 1.0770(3) 0.8421(8) -0.0676(2) 0.0219(11) Uani 1 1 d . . .
N8 N 1.0993(3) 0.4404(8) 0.3888(2) 0.0248(12) Uani 1 1 d . . .
C5 C 0.9705(3) 0.9997(9) -0.2824(2) 0.0178(12) Uani 1 1 d . A .
C8 C 1.0203(3) 0.9101(9) -0.1630(2) 0.0162(11) Uani 1 1 d . . .
C3 C 0.8349(3) 0.4858(9) 0.2078(2) 0.0179(12) Uani 1 1 d . . .
N9 N 1.0711(2) 0.4929(8) 0.3239(2) 0.0237(12) Uani 1 1 d . . .
C2 C 0.8909(3) 0.5532(9) 0.1628(2) 0.0181(12) Uani 1 1 d . . .
C4 C 0.9953(3) 0.4516(9) 0.3252(2) 0.0168(12) Uani 1 1 d . . .
C1 C 0.9628(3) 0.5511(9) 0.2027(2) 0.0149(11) Uani 1 1 d . . .
O10 O 0.7296(5) 0.8836(18) -0.2127(5) 0.0336(16) Uani 0.500(7) 1 d PU A 2
O9 O 0.7368(5) 0.7828(16) -0.3183(4) 0.0348(16) Uani 0.500(7) 1 d PU A 2
C6 C 0.8935(3) 0.9899(9) -0.3140(2) 0.0172(12) Uani 1 1 d . . .
K2 K 0.85140(7) 0.6979(2) -0.07549(5) 0.0234(3) Uani 1 1 d . . .
O11 O 0.8818(2) 0.2953(7) -0.07023(18) 0.0258(10) Uani 1 1 d . A .
H11A H 0.9028 0.2584 -0.0314 0.039 Uiso 1 1 d R . .
H11B H 0.8489 0.2085 -0.0847 0.039 Uiso 1 1 d R . .
O12 O 0.7529(2) 1.0050(7) -0.04957(18) 0.0274(10) Uani 1 1 d . A .
H12A H 0.7543 1.0733 -0.0127 0.041 Uiso 1 1 d R . .
H12B H 0.7121 1.0369 -0.0744 0.041 Uiso 1 1 d R . .
O14 O 0.5997(2) 0.3353(7) 0.05750(18) 0.0264(10) Uani 1 1 d . . .
H14A H 0.6391 0.2660 0.0716 0.040 Uiso 1 1 d R A .
H14B H 0.5730 0.2624 0.0289 0.040 Uiso 1 1 d R . .
O13 O 0.7093(2) 1.0432(7) 0.10032(17) 0.0235(9) Uani 1 1 d . . .
H13A H 0.7573 1.0294 0.1138 0.035 Uiso 1 1 d R A .
H13B H 0.6950 1.1595 0.1086 0.035 Uiso 1 1 d R . .
O8 O 0.7411(5) 0.7679(18) -0.2154(5) 0.0299(13) Uani 0.500(7) 1 d PU A 1
O7 O 0.7152(4) 0.9676(15) -0.3021(4) 0.0292(12) Uani 0.500(7) 1 d PU . 1


_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
K1 O2 3.078(4) . ?
K1 N11 3.220(4) 2_644 ?
K1 O5 2.740(4) 2_644 ?
K1 O3 2.692(4) . ?
K1 O6 2.938(4) 2_644 ?
K1 N6 2.826(5) 2_655 ?
K1 K2 4.2426(17) . ?
K1 O12 3.256(4) . ?
K1 O14 2.722(5) . ?
K1 O13 2.750(4) . ?
O2 N2 1.239(5) . ?
O2 K2 2.830(4) . ?
N18 N17 1.351(6) . ?
N18 C8 1.324(7) . ?
N11 K1 3.220(4) 2_654 ?
N11 O5 1.246(6) . ?
N11 O6 1.243(5) . ?
N11 C6 1.405(6) . ?
O5 K1 2.740(4) 2_654 ?
N15 N16 1.359(6) . ?
N15 C8 1.321(7) . ?
N15 K2 2.869(5) . ?
N5 N4 1.377(6) . ?
N5 C4 1.417(6) . ?
N5 C1 1.375(6) . ?
O1 N2 1.239(6) . ?
O1 K2 3.047(4) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C5 1.314(7) . ?
N7 N6 1.366(6) . ?
N7 N8 1.323(6) . ?
O4 N3 1.211(6) . ?
O3 N3 1.236(6) . ?
N4 C3 1.308(6) . ?
O6 K1 2.938(4) 2_654 ?
O6 K2 2.900(4) 2_654 ?
N13 C7 1.303(6) . ?
N13 N14 1.375(6) . ?
N13 K2 2.885(4) . ?
C7 N12 1.447(7) . ?
C7 C6 1.402(7) . ?
N14 C5 1.371(6) . ?
N14 C8 1.405(6) . ?
N12 O10 1.164(10) . ?
N12 O9 1.294(10) . ?
N12 O8 1.249(10) . ?
N12 O7 1.261(9) . ?
N17 N16 1.309(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.322(7) . ?
N3 C3 1.454(6) . ?
N2 C2 1.405(6) . ?
N2 K2 3.323(4) . ?
N6 K1 2.826(5) 2_645 ?
N6 C4 1.333(6) . ?
N8 N9 1.366(6) . ?
C5 C6 1.420(7) . ?
C3 C2 1.408(7) . ?
N9 C4 1.325(7) . ?
C2 C1 1.412(7) . ?
K2 O6 2.900(4) 2_644 ?
K2 O11 2.801(5) . ?
K2 O12 2.754(5) . ?
K2 O8 3.242(9) . ?
K2 O7 3.011(8) 2_644 ?
O11 H11A 0.8518 . ?
O11 H11B 0.8532 . ?
O12 H12A 0.8521 . ?
O12 H12B 0.8509 . ?
O14 H14A 0.8548 . ?
O14 H14B 0.8566 . ?
O13 H13A 0.8504 . ?
O13 H13B 0.8499 . ?
O7 K2 3.011(8) 2_654 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 K1 N11 94.65(11) . 2_644 ?
O2 K1 K2 41.81(7) . . ?
O2 K1 O12 72.27(11) . . ?
N11 K1 K2 63.76(8) 2_644 . ?
N11 K1 O12 75.96(12) 2_644 . ?
O5 K1 O2 116.64(11) 2_644 . ?
O5 K1 N11 22.33(11) 2_644 2_644 ?
O5 K1 O6 45.01(10) 2_644 2_644 ?
O5 K1 N6 103.42(12) 2_644 2_655 ?
O5 K1 K2 84.95(8) 2_644 . ?
O5 K1 O12 87.39(11) 2_644 . ?
O5 K1 O13 137.66(14) 2_644 . ?
O3 K1 O2 55.12(11) . . ?
O3 K1 N11 137.79(14) . 2_644 ?
O3 K1 O5 148.27(15) . 2_644 ?
O3 K1 O6 120.71(13) . 2_644 ?
O3 K1 N6 87.37(12) . 2_655 ?
O3 K1 K2 96.54(9) . . ?
O3 K1 O12 114.12(11) . . ?
O3 K1 O14 74.07(13) . . ?
O3 K1 O13 73.91(13) . . ?
O6 K1 O2 72.18(10) 2_644 . ?
O6 K1 N11 22.69(10) 2_644 2_644 ?
O6 K1 K2 43.04(8) 2_644 . ?
O6 K1 O12 66.58(12) 2_644 . ?
N6 K1 O2 139.41(11) 2_655 . ?
N6 K1 N11 125.69(12) 2_655 2_644 ?
N6 K1 O6 148.33(11) 2_655 2_644 ?
N6 K1 K2 157.20(12) 2_655 . ?
N6 K1 O12 117.83(14) 2_655 . ?
O12 K1 K2 40.47(8) . . ?
O14 K1 O2 89.44(13) . . ?
O14 K1 N11 77.35(12) . 2_644 ?
O14 K1 O5 75.33(13) . 2_644 ?
O14 K1 O6 80.80(13) . 2_644 ?
O14 K1 N6 94.82(14) . 2_655 ?
O14 K1 K2 107.87(9) . . ?
O14 K1 O12 146.02(12) . . ?
O14 K1 O13 146.25(11) . . ?
O13 K1 O2 80.92(12) . . ?
O13 K1 N11 135.34(13) . 2_644 ?
O13 K1 O6 125.47(12) . 2_644 ?
O13 K1 N6 73.36(13) . 2_655 ?
O13 K1 K2 86.12(8) . . ?
O13 K1 O12 60.27(11) . . ?
N2 O2 K1 146.5(4) . . ?
N2 O2 K2 102.4(3) . . ?
K2 O2 K1 91.71(11) . . ?
C8 N18 N17 102.4(4) . . ?
O5 N11 K1 56.7(2) . 2_654 ?
O5 N11 C6 116.9(4) . . ?
O6 N11 K1 65.8(3) . 2_654 ?
O6 N11 O5 122.4(4) . . ?
O6 N11 C6 120.7(4) . . ?
C6 N11 K1 173.2(3) . 2_654 ?
N11 O5 K1 101.0(3) . 2_654 ?
N16 N15 K2 136.7(3) . . ?
C8 N15 N16 102.3(4) . . ?
C8 N15 K2 120.7(3) . . ?
N4 N5 C4 119.8(4) . . ?
C1 N5 N4 113.3(4) . . ?
C1 N5 C4 126.9(4) . . ?
N2 O1 K2 91.7(3) . . ?
H10A N10 H10B 120.0 . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
N8 N7 N6 109.9(4) . . ?
N3 O3 K1 151.2(3) . . ?
C3 N4 N5 104.0(4) . . ?
N11 O6 K1 91.5(3) . 2_654 ?
N11 O6 K2 151.5(4) . 2_654 ?
K2 O6 K1 93.22(12) 2_654 2_654 ?
C7 N13 N14 104.5(4) . . ?
C7 N13 K2 135.3(3) . . ?
N14 N13 K2 119.9(3) . . ?
N13 C7 N12 114.9(5) . . ?
N13 C7 C6 112.9(4) . . ?
C6 C7 N12 132.2(4) . . ?
N13 N14 C8 118.9(4) . . ?
C5 N14 N13 113.4(4) . . ?
C5 N14 C8 127.6(4) . . ?
O10 N12 C7 121.2(6) . . ?
O10 N12 O9 123.5(8) . . ?
O10 N12 O8 39.4(6) . . ?
O10 N12 O7 97.6(7) . . ?
O9 N12 C7 113.5(6) . . ?
O8 N12 C7 117.2(6) . . ?
O8 N12 O9 103.1(7) . . ?
O8 N12 O7 121.4(6) . . ?
O7 N12 C7 120.1(6) . . ?
O7 N12 O9 64.2(6) . . ?
N16 N17 N18 110.1(4) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
O4 N3 O3 125.1(4) . . ?
O4 N3 C3 117.8(4) . . ?
O3 N3 C3 117.1(5) . . ?
O2 N2 C2 119.5(4) . . ?
O2 N2 K2 56.3(2) . . ?
O1 N2 O2 122.7(4) . . ?
O1 N2 C2 117.8(4) . . ?
O1 N2 K2 66.4(2) . . ?
C2 N2 K2 175.5(4) . . ?
N7 N6 K1 108.3(3) . 2_645 ?
C4 N6 K1 149.3(3) . 2_645 ?
C4 N6 N7 102.2(4) . . ?
N17 N16 N15 109.9(4) . . ?
N7 N8 N9 109.6(4) . . ?
N10 C5 N14 123.9(4) . . ?
N10 C5 C6 132.5(5) . . ?
N14 C5 C6 103.6(4) . . ?
N18 C8 N14 122.4(4) . . ?
N15 C8 N18 115.3(4) . . ?
N15 C8 N14 122.3(5) . . ?
N4 C3 N3 116.3(4) . . ?
N4 C3 C2 113.4(4) . . ?
C2 C3 N3 130.1(4) . . ?
C4 N9 N8 102.6(4) . . ?
N2 C2 C3 130.4(4) . . ?
N2 C2 C1 124.5(5) . . ?
C3 C2 C1 105.0(4) . . ?
N6 C4 N5 123.3(4) . . ?
N9 C4 N5 121.1(4) . . ?
N9 C4 N6 115.6(4) . . ?
N5 C1 C2 104.3(4) . . ?
N1 C1 N5 123.3(4) . . ?
N1 C1 C2 132.4(5) . . ?
N11 C6 C5 122.8(5) . . ?
C7 C6 N11 131.7(4) . . ?
C7 C6 C5 105.5(4) . . ?
O2 K2 K1 46.48(8) . . ?
O2 K2 N15 119.49(11) . . ?
O2 K2 O1 43.23(10) . . ?
O2 K2 O6 76.45(11) . 2_644 ?
O2 K2 N13 171.19(15) . . ?
O2 K2 N2 21.36(10) . . ?
O2 K2 O8 132.83(17) . . ?
O2 K2 O7 119.5(2) . 2_644 ?
N15 K2 K1 150.98(10) . . ?
N15 K2 O1 76.26(11) . . ?
N15 K2 O6 163.33(11) . 2_644 ?
N15 K2 N13 57.74(12) . . ?
N15 K2 N2 98.13(11) . . ?
N15 K2 O8 107.16(18) . . ?
N15 K2 O7 110.09(18) . 2_644 ?
O1 K2 K1 85.66(7) . . ?
O1 K2 N2 21.88(10) . . ?
O1 K2 O8 172.8(2) . . ?
O6 K2 K1 43.74(8) 2_644 . ?
O6 K2 O1 119.41(11) 2_644 . ?
O6 K2 N2 97.67(11) 2_644 . ?
O6 K2 O8 58.00(18) 2_644 . ?
O6 K2 O7 54.16(17) 2_644 2_644 ?
N13 K2 K1 131.22(9) . . ?
N13 K2 O1 133.20(12) . . ?
N13 K2 O6 107.28(12) . 2_644 ?
N13 K2 N2 154.39(13) . . ?
N13 K2 O8 49.47(17) . . ?
N13 K2 O7 68.3(2) . 2_644 ?
N2 K2 K1 65.54(8) . . ?
O11 K2 K1 99.13(8) . . ?
O11 K2 O2 74.28(12) . . ?
O11 K2 N15 99.62(13) . . ?
O11 K2 O1 79.49(12) . . ?
O11 K2 O6 79.20(13) . 2_644 ?
O11 K2 N13 114.05(13) . . ?
O11 K2 N2 75.73(12) . . ?
O11 K2 O8 105.8(2) . . ?
O11 K2 O7 64.88(19) . 2_644 ?
O12 K2 K1 50.13(9) . . ?
O12 K2 O2 84.05(13) . . ?
O12 K2 N15 110.50(14) . . ?
O12 K2 O1 99.85(12) . . ?
O12 K2 O6 74.14(13) . 2_644 ?
O12 K2 N13 89.28(13) . . ?
O12 K2 N2 92.09(12) . . ?
O12 K2 O11 148.90(12) . . ?
O12 K2 O8 73.1(2) . . ?
O12 K2 O7 109.62(17) . 2_644 ?
O8 K2 K1 88.66(16) . . ?
O8 K2 N2 153.83(18) . . ?
O7 K2 K1 97.87(15) 2_644 . ?
O7 K2 O1 144.3(2) 2_644 . ?
O7 K2 N2 134.3(2) 2_644 . ?
O7 K2 O8 41.1(3) 2_644 . ?
K2 O11 H11A 113.0 . . ?
K2 O11 H11B 123.7 . . ?
H11A O11 H11B 108.5 . . ?
K1 O12 H12A 83.5 . . ?
K1 O12 H12B 89.5 . . ?
K2 O12 K1 89.40(13) . . ?
K2 O12 H12A 125.6 . . ?
K2 O12 H12B 125.5 . . ?
H12A O12 H12B 108.3 . . ?
K1 O14 H14A 109.5 . . ?
K1 O14 H14B 127.8 . . ?
H14A O14 H14B 105.3 . . ?
K1 O13 H13A 112.6 . . ?
K1 O13 H13B 138.1 . . ?
H13A O13 H13B 109.2 . . ?
N12 O8 K2 121.1(5) . . ?
N12 O7 K2 160.2(5) . 2_654 ?

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
K1 O2 N2 O1 -112.1(6) . . . . ?
K1 O2 N2 C2 69.1(9) . . . . ?
K1 O2 N2 K2 -112.7(6) . . . . ?
K1 O2 K2 N15 148.04(14) . . . . ?
K1 O2 K2 O1 149.1(2) . . . . ?
K1 O2 K2 O6 -37.26(13) . . . 2_644 ?
K1 O2 K2 N13 78.8(8) . . . . ?
K1 O2 K2 N2 149.4(4) . . . . ?
K1 O2 K2 O11 -119.65(13) . . . . ?
K1 O2 K2 O12 37.83(12) . . . . ?
K1 O2 K2 O8 -22.4(4) . . . . ?
K1 O2 K2 O7 -71.4(2) . . . 2_644 ?
K1 N11 O6 K2 -99.6(7) 2_654 . . 2_654 ?
K1 N11 C6 C7 162(3) 2_654 . . . ?
K1 N11 C6 C5 -16(4) 2_654 . . . ?
K1 O3 N3 O4 -82.0(8) . . . . ?
K1 O3 N3 C3 101.6(7) . . . . ?
K1 N6 C4 N5 4.6(12) 2_645 . . . ?
K1 N6 C4 N9 -174.0(5) 2_645 . . . ?
K1 K2 O8 N12 142.6(8) . . . . ?
O2 K1 O3 N3 -61.8(7) . . . . ?
O2 K1 K2 N15 -71.8(2) . . . . ?
O2 K1 K2 O1 -20.69(16) . . . . ?
O2 K1 K2 O6 121.7(2) . . . 2_644 ?
O2 K1 K2 N13 -168.5(2) . . . . ?
O2 K1 K2 N2 -11.76(17) . . . . ?
O2 K1 K2 O11 57.92(15) . . . . ?
O2 K1 K2 O12 -127.37(17) . . . . ?
O2 K1 K2 O8 163.7(3) . . . . ?
O2 K1 K2 O7 123.6(2) . . . 2_644 ?
O2 K1 O12 K2 33.79(10) . . . . ?
O2 N2 C2 C3 -4.2(10) . . . . ?
O2 N2 C2 C1 171.6(6) . . . . ?
O2 N2 K2 K1 23.9(3) . . . . ?
O2 N2 K2 N15 178.8(4) . . . . ?
O2 N2 K2 O1 179.4(6) . . . . ?
O2 N2 K2 O6 -6.5(4) . . . 2_644 ?
O2 N2 K2 N13 160.5(4) . . . . ?
O2 N2 K2 O11 -83.3(4) . . . . ?
O2 N2 K2 O12 67.8(4) . . . . ?
O2 N2 K2 O8 13.7(7) . . . . ?
O2 N2 K2 O7 -52.6(4) . . . 2_644 ?
O2 K2 O12 K1 -35.41(10) . . . . ?
O2 K2 O8 N12 158.7(7) . . . . ?
N18 N17 N16 N15 0.7(7) . . . . ?
N11 K1 O2 N2 156.5(6) 2_644 . . . ?
N11 K1 O2 K2 40.86(15) 2_644 . . . ?
N11 K1 O3 N3 -10.2(8) 2_644 . . . ?
N11 K1 K2 O2 -133.37(18) 2_644 . . . ?
N11 K1 K2 N15 154.9(2) 2_644 . . . ?
N11 K1 K2 O1 -154.05(15) 2_644 . . . ?
N11 K1 K2 O6 -11.71(18) 2_644 . . 2_644 ?
N11 K1 K2 N13 58.16(17) 2_644 . . . ?
N11 K1 K2 N2 -145.12(15) 2_644 . . . ?
N11 K1 K2 O11 -75.45(13) 2_644 . . . ?
N11 K1 K2 O12 99.27(15) 2_644 . . . ?
N11 K1 K2 O8 30.4(2) 2_644 . . . ?
N11 K1 K2 O7 -9.8(2) 2_644 . . 2_644 ?
N11 K1 O12 K2 -65.85(12) 2_644 . . . ?
O5 K1 O2 N2 160.5(6) 2_644 . . . ?
O5 K1 O2 K2 44.87(18) 2_644 . . . ?
O5 K1 O3 N3 23.2(8) 2_644 . . . ?
O5 K1 K2 O2 -140.73(17) 2_644 . . . ?
O5 K1 K2 N15 147.5(2) 2_644 . . . ?
O5 K1 K2 O1 -161.41(14) 2_644 . . . ?
O5 K1 K2 O6 -19.07(17) 2_644 . . 2_644 ?
O5 K1 K2 N13 50.80(17) 2_644 . . . ?
O5 K1 K2 N2 -152.48(15) 2_644 . . . ?
O5 K1 K2 O11 -82.81(13) 2_644 . . . ?
O5 K1 K2 O12 91.91(14) 2_644 . . . ?
O5 K1 K2 O8 23.0(2) 2_644 . . . ?
O5 K1 K2 O7 -17.1(2) 2_644 . . 2_644 ?
O5 K1 O12 K2 -85.27(12) 2_644 . . . ?
O5 N11 O6 K1 -1.4(6) . . . 2_654 ?
O5 N11 O6 K2 -101.0(7) . . . 2_654 ?
O5 N11 C6 C7 179.2(6) . . . . ?
O5 N11 C6 C5 0.8(9) . . . . ?
N15 K2 O12 K1 -154.71(10) . . . . ?
N15 K2 O8 N12 -12.6(9) . . . . ?
N5 N4 C3 N3 -176.2(5) . . . . ?
N5 N4 C3 C2 -0.2(7) . . . . ?
O1 N2 C2 C3 176.9(6) . . . . ?
O1 N2 C2 C1 -7.3(9) . . . . ?
O1 N2 K2 K1 -155.5(4) . . . . ?
O1 N2 K2 O2 -179.4(6) . . . . ?
O1 N2 K2 N15 -0.6(4) . . . . ?
O1 N2 K2 O6 174.1(3) . . . 2_644 ?
O1 N2 K2 N13 -18.9(5) . . . . ?
O1 N2 K2 O11 97.3(3) . . . . ?
O1 N2 K2 O12 -111.6(3) . . . . ?
O1 N2 K2 O8 -165.7(6) . . . . ?
O1 N2 K2 O7 128.0(4) . . . 2_644 ?
O1 K2 O12 K1 -75.80(11) . . . . ?
O1 K2 O8 N12 104.8(14) . . . . ?
N10 C5 C6 N11 -0.4(11) . . . . ?
N10 C5 C6 C7 -179.2(7) . . . . ?
N7 N6 C4 N5 179.3(6) . . . . ?
N7 N6 C4 N9 0.7(7) . . . . ?
N7 N8 N9 C4 -0.7(7) . . . . ?
O4 N3 C3 N4 -34.6(8) . . . . ?
O4 N3 C3 C2 150.2(6) . . . . ?
O3 K1 O2 N2 -55.3(6) . . . . ?
O3 K1 O2 K2 -171.0(2) . . . . ?
O3 K1 K2 O2 7.41(17) . . . . ?
O3 K1 K2 N15 -64.4(2) . . . . ?
O3 K1 K2 O1 -13.27(14) . . . . ?
O3 K1 K2 O6 129.07(18) . . . 2_644 ?
O3 K1 K2 N13 -161.07(17) . . . . ?
O3 K1 K2 N2 -4.35(14) . . . . ?
O3 K1 K2 O11 65.33(13) . . . . ?
O3 K1 K2 O12 -119.96(15) . . . . ?
O3 K1 K2 O8 171.1(2) . . . . ?
O3 K1 K2 O7 131.0(2) . . . 2_644 ?
O3 K1 O12 K2 70.58(15) . . . . ?
O3 N3 C3 N4 142.1(5) . . . . ?
O3 N3 C3 C2 -33.1(9) . . . . ?
N4 N5 C4 N6 3.4(9) . . . . ?
N4 N5 C4 N9 -178.1(5) . . . . ?
N4 N5 C1 N1 179.7(5) . . . . ?
N4 N5 C1 C2 -1.2(7) . . . . ?
N4 C3 C2 N2 176.0(6) . . . . ?
N4 C3 C2 C1 -0.5(7) . . . . ?
O6 K1 O2 N2 153.3(6) 2_644 . . . ?
O6 K1 O2 K2 37.60(13) 2_644 . . . ?
O6 K1 O3 N3 -29.8(7) 2_644 . . . ?
O6 K1 K2 O2 -121.7(2) 2_644 . . . ?
O6 K1 K2 N15 166.6(3) 2_644 . . . ?
O6 K1 K2 O1 -142.35(17) 2_644 . . . ?
O6 K1 K2 N13 69.9(2) 2_644 . . . ?
O6 K1 K2 N2 -133.42(18) 2_644 . . . ?
O6 K1 K2 O11 -63.74(16) 2_644 . . . ?
O6 K1 K2 O12 110.97(17) 2_644 . . . ?
O6 K1 K2 O8 42.1(3) 2_644 . . . ?
O6 K1 K2 O7 1.9(2) 2_644 . . 2_644 ?
O6 K1 O12 K2 -43.99(11) 2_644 . . . ?
O6 N11 O5 K1 1.5(6) . . . 2_654 ?
O6 N11 C6 C7 0.0(10) . . . . ?
O6 N11 C6 C5 -178.4(6) . . . . ?
O6 K2 O12 K1 42.16(10) 2_644 . . . ?
O6 K2 O8 N12 175.7(10) 2_644 . . . ?
N13 C7 N12 O10 30.3(11) . . . . ?
N13 C7 N12 O9 -135.0(7) . . . . ?
N13 C7 N12 O8 -14.9(10) . . . . ?
N13 C7 N12 O7 152.3(7) . . . . ?
N13 C7 C6 N11 -179.7(6) . . . . ?
N13 C7 C6 C5 -1.1(7) . . . . ?
N13 N14 C5 N10 179.6(5) . . . . ?
N13 N14 C5 C6 -0.5(7) . . . . ?
N13 N14 C8 N18 -179.6(5) . . . . ?
N13 N14 C8 N15 1.9(8) . . . . ?
N13 K2 O12 K1 150.36(11) . . . . ?
N13 K2 O8 N12 -9.9(7) . . . . ?
C7 N13 N14 C5 -0.2(7) . . . . ?
C7 N13 N14 C8 178.8(5) . . . . ?
C7 N13 K2 K1 -36.4(6) . . . . ?
C7 N13 K2 O2 -107.5(9) . . . . ?
C7 N13 K2 N15 178.3(6) . . . . ?
C7 N13 K2 O1 -169.6(5) . . . . ?
C7 N13 K2 O6 6.4(6) . . . 2_644 ?
C7 N13 K2 N2 -160.1(5) . . . . ?
C7 N13 K2 O11 92.0(6) . . . . ?
C7 N13 K2 O12 -66.8(6) . . . . ?
C7 N13 K2 O8 1.4(6) . . . . ?
C7 N13 K2 O7 44.7(6) . . . 2_644 ?
C7 N12 O8 K2 16.9(11) . . . . ?
C7 N12 O7 K2 30(2) . . . 2_654 ?
N14 N13 C7 N12 179.4(5) . . . . ?
N14 N13 C7 C6 0.8(7) . . . . ?
N14 N13 K2 K1 150.5(3) . . . . ?
N14 N13 K2 O2 79.5(9) . . . . ?
N14 N13 K2 N15 5.2(4) . . . . ?
N14 N13 K2 O1 17.3(5) . . . . ?
N14 N13 K2 O6 -166.7(4) . . . 2_644 ?
N14 N13 K2 N2 26.8(6) . . . . ?
N14 N13 K2 O11 -81.0(4) . . . . ?
N14 N13 K2 O12 120.2(4) . . . . ?
N14 N13 K2 O8 -171.7(5) . . . . ?
N14 N13 K2 O7 -128.3(4) . . . 2_644 ?
N14 C5 C6 N11 179.6(5) . . . . ?
N14 C5 C6 C7 0.9(6) . . . . ?
N12 C7 C6 N11 2.0(12) . . . . ?
N12 C7 C6 C5 -179.4(6) . . . . ?
N17 N18 C8 N15 0.2(7) . . . . ?
N17 N18 C8 N14 -178.4(5) . . . . ?
N3 C3 C2 N2 -8.7(11) . . . . ?
N3 C3 C2 C1 174.8(6) . . . . ?
N2 O2 K2 K1 -149.4(4) . . . . ?
N2 O2 K2 N15 -1.3(4) . . . . ?
N2 O2 K2 O1 -0.3(3) . . . . ?
N2 O2 K2 O6 173.4(4) . . . 2_644 ?
N2 O2 K2 N13 -70.6(9) . . . . ?
N2 O2 K2 O11 91.0(4) . . . . ?
N2 O2 K2 O12 -111.6(4) . . . . ?
N2 O2 K2 O8 -171.8(4) . . . . ?
N2 O2 K2 O7 139.3(4) . . . 2_644 ?
N2 O1 K2 K1 22.3(3) . . . . ?
N2 O1 K2 O2 0.3(3) . . . . ?
N2 O1 K2 N15 179.4(4) . . . . ?
N2 O1 K2 O6 -6.7(4) . . . 2_644 ?
N2 O1 K2 N13 168.9(3) . . . . ?
N2 O1 K2 O11 -77.9(3) . . . . ?
N2 O1 K2 O12 70.5(4) . . . . ?
N2 O1 K2 O8 60.2(17) . . . . ?
N2 O1 K2 O7 -75.2(4) . . . 2_644 ?
N2 C2 C1 N5 -175.8(6) . . . . ?
N2 C2 C1 N1 3.2(11) . . . . ?
N2 K2 O12 K1 -55.22(11) . . . . ?
N2 K2 O8 N12 152.0(6) . . . . ?
N6 K1 O2 N2 -29.4(7) 2_655 . . . ?
N6 K1 O2 K2 -145.13(18) 2_655 . . . ?
N6 K1 O3 N3 134.7(7) 2_655 . . . ?
N6 K1 K2 O2 106.3(3) 2_655 . . . ?
N6 K1 K2 N15 34.5(3) 2_655 . . . ?
N6 K1 K2 O1 85.6(2) 2_655 . . . ?
N6 K1 K2 O6 -132.1(3) 2_655 . . 2_644 ?
N6 K1 K2 N13 -62.2(3) 2_655 . . . ?
N6 K1 K2 N2 94.5(3) 2_655 . . . ?
N6 K1 K2 O11 164.2(2) 2_655 . . . ?
N6 K1 K2 O12 -21.1(2) 2_655 . . . ?
N6 K1 K2 O8 -90.0(3) 2_655 . . . ?
N6 K1 K2 O7 -130.2(3) 2_655 . . 2_644 ?
N6 K1 O12 K2 170.92(11) 2_655 . . . ?
N6 N7 N8 N9 1.1(7) . . . . ?
N16 N15 C8 N18 0.1(7) . . . . ?
N16 N15 C8 N14 178.8(5) . . . . ?
N16 N15 K2 K1 64.4(7) . . . . ?
N16 N15 K2 O2 12.1(6) . . . . ?
N16 N15 K2 O1 11.4(5) . . . . ?
N16 N15 K2 O6 -149.7(5) . . . 2_644 ?
N16 N15 K2 N13 -177.6(6) . . . . ?
N16 N15 K2 N2 11.6(6) . . . . ?
N16 N15 K2 O11 -65.2(6) . . . . ?
N16 N15 K2 O12 106.9(5) . . . . ?
N16 N15 K2 O8 -175.2(6) . . . . ?
N16 N15 K2 O7 -131.8(6) . . . 2_644 ?
N8 N7 N6 K1 176.1(4) . . . 2_645 ?
N8 N7 N6 C4 -1.1(6) . . . . ?
N8 N9 C4 N5 -178.7(5) . . . . ?
N8 N9 C4 N6 0.0(7) . . . . ?
C5 N14 C8 N18 -0.7(9) . . . . ?
C5 N14 C8 N15 -179.2(6) . . . . ?
C8 N18 N17 N16 -0.5(6) . . . . ?
C8 N15 N16 N17 -0.5(7) . . . . ?
C8 N15 K2 K1 -122.3(4) . . . . ?
C8 N15 K2 O2 -174.6(4) . . . . ?
C8 N15 K2 O1 -175.3(5) . . . . ?
C8 N15 K2 O6 23.7(8) . . . 2_644 ?
C8 N15 K2 N13 -4.3(4) . . . . ?
C8 N15 K2 N2 -175.1(4) . . . . ?
C8 N15 K2 O11 108.1(4) . . . . ?
C8 N15 K2 O12 -79.7(5) . . . . ?
C8 N15 K2 O8 -1.9(5) . . . . ?
C8 N15 K2 O7 41.5(5) . . . 2_644 ?
C8 N14 C5 N10 0.7(10) . . . . ?
C8 N14 C5 C6 -179.4(6) . . . . ?
C3 C2 C1 N5 0.9(6) . . . . ?
C3 C2 C1 N1 179.9(6) . . . . ?
C2 N2 K2 K1 44(5) . . . . ?
C2 N2 K2 O2 21(5) . . . . ?
C2 N2 K2 N15 -161(5) . . . . ?
C2 N2 K2 O1 -160(5) . . . . ?
C2 N2 K2 O6 14(5) . . . 2_644 ?
C2 N2 K2 N13 -179(100) . . . . ?
C2 N2 K2 O11 -63(5) . . . . ?
C2 N2 K2 O12 88(5) . . . . ?
C2 N2 K2 O8 34(5) . . . . ?
C2 N2 K2 O7 -32(5) . . . 2_644 ?
C4 N5 N4 C3 179.6(5) . . . . ?
C4 N5 C1 N1 1.2(10) . . . . ?
C4 N5 C1 C2 -179.7(6) . . . . ?
C1 N5 N4 C3 0.9(7) . . . . ?
C1 N5 C4 N6 -178.1(6) . . . . ?
C1 N5 C4 N9 0.4(9) . . . . ?
O10 N12 O8 K2 -90.0(11) . . . . ?
O10 N12 O7 K2 163.0(18) . . . 2_654 ?
O9 N12 O8 K2 142.4(7) . . . . ?
O9 N12 O7 K2 -73.3(19) . . . 2_654 ?
C6 N11 O5 K1 -177.7(4) . . . 2_654 ?
C6 N11 O6 K1 177.8(5) . . . 2_654 ?
C6 N11 O6 K2 78.2(9) . . . 2_654 ?
C6 C7 N12 O10 -151.3(9) . . . . ?
C6 C7 N12 O9 43.4(10) . . . . ?
C6 C7 N12 O8 163.4(8) . . . . ?
C6 C7 N12 O7 -29.4(11) . . . . ?
K2 K1 O2 N2 115.7(7) . . . . ?
K2 K1 O3 N3 -67.8(7) . . . . ?
K2 O2 N2 O1 0.7(6) . . . . ?
K2 O2 N2 C2 -178.2(4) . . . . ?
K2 N15 N16 N17 173.6(4) . . . . ?
K2 N15 C8 N18 -175.2(4) . . . . ?
K2 N15 C8 N14 3.5(8) . . . . ?
K2 O1 N2 O2 -0.6(6) . . . . ?
K2 O1 N2 C2 178.3(5) . . . . ?
K2 N13 C7 N12 5.7(8) . . . . ?
K2 N13 C7 C6 -173.0(4) . . . . ?
K2 N13 N14 C5 174.8(4) . . . . ?
K2 N13 N14 C8 -6.2(6) . . . . ?
K2 N2 C2 C3 -24(5) . . . . ?
K2 N2 C2 C1 152(5) . . . . ?
O11 K2 O12 K1 10.1(2) . . . . ?
O11 K2 O8 N12 -118.3(8) . . . . ?
O12 K1 O2 N2 82.9(6) . . . . ?
O12 K1 O2 K2 -32.79(11) . . . . ?
O12 K1 O3 N3 -105.8(7) . . . . ?
O12 K1 K2 O2 127.37(17) . . . . ?
O12 K1 K2 N15 55.6(2) . . . . ?
O12 K1 K2 O1 106.68(14) . . . . ?
O12 K1 K2 O6 -110.97(17) . . . 2_644 ?
O12 K1 K2 N13 -41.11(17) . . . . ?
O12 K1 K2 N2 115.61(15) . . . . ?
O12 K1 K2 O11 -174.71(13) . . . . ?
O12 K1 K2 O8 -68.9(2) . . . . ?
O12 K1 K2 O7 -109.0(2) . . . 2_644 ?
O12 K2 O8 N12 94.2(9) . . . . ?
O14 K1 O2 N2 -126.2(6) . . . . ?
O14 K1 O2 K2 118.12(13) . . . . ?
O14 K1 O3 N3 39.0(7) . . . . ?
O14 K1 K2 O2 -67.92(16) . . . . ?
O14 K1 K2 N15 -139.7(2) . . . . ?
O14 K1 K2 O1 -88.60(13) . . . . ?
O14 K1 K2 O6 53.74(16) . . . 2_644 ?
O14 K1 K2 N13 123.61(16) . . . . ?
O14 K1 K2 N2 -79.68(13) . . . . ?
O14 K1 K2 O11 -10.00(11) . . . . ?
O14 K1 K2 O12 164.71(13) . . . . ?
O14 K1 K2 O8 95.8(2) . . . . ?
O14 K1 K2 O7 55.7(2) . . . 2_644 ?
O14 K1 O12 K2 -26.7(2) . . . . ?
O13 K1 O2 N2 21.3(6) . . . . ?
O13 K1 O2 K2 -94.35(13) . . . . ?
O13 K1 O3 N3 -151.8(7) . . . . ?
O13 K1 K2 O2 80.71(15) . . . . ?
O13 K1 K2 N15 8.9(2) . . . . ?
O13 K1 K2 O1 60.02(13) . . . . ?
O13 K1 K2 O6 -157.63(17) . . . 2_644 ?
O13 K1 K2 N13 -87.77(16) . . . . ?
O13 K1 K2 N2 68.95(13) . . . . ?
O13 K1 K2 O11 138.63(11) . . . . ?
O13 K1 K2 O12 -46.66(13) . . . . ?
O13 K1 K2 O8 -115.6(2) . . . . ?
O13 K1 K2 O7 -155.7(2) . . . 2_644 ?
O13 K1 O12 K2 123.32(14) . . . . ?
O8 N12 O7 K2 -163.3(16) . . . 2_654 ?
O8 K2 O12 K1 102.85(19) . . . . ?
O7 N12 O8 K2 -150.1(7) . . . . ?
O7 K2 O12 K1 83.8(2) 2_644 . . . ?
O7 K2 O8 N12 -113.8(9) 2_644 . . . ?

####################################################################### 
# 
# 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_bl85
_database_code_depnum_ccdc_archive 'CCDC 1449634'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H5 N9 O5'
_chemical_formula_weight         259.17

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   4.7451(9)
_cell_length_b                   7.1473(14)
_cell_length_c                   27.902(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.22(3)
_cell_angle_gamma                90.00
_cell_volume                     946.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2746
_cell_measurement_theta_min      1.4597
_cell_measurement_theta_max      27.4662

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8552
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6342
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2134
_reflns_number_gt                1797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.1102P)²+1.1225P] 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         2134
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.1968
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_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 0.4110(6) 0.3181(4) 0.32335(10) 0.0386(7) Uani 1 1 d . . .
O2 O 0.6162(6) 0.5299(4) 0.25078(9) 0.0391(7) Uani 1 1 d . . .
N3 N 0.8624(6) 1.0104(4) 0.33264(10) 0.0288(7) Uani 1 1 d . . .
H3A H 0.9316 0.9994 0.3032 0.035 Uiso 1 1 d R . .
H3B H 0.8024 1.1203 0.3436 0.035 Uiso 1 1 d R . .
N4 N 0.4890(6) 0.8824(4) 0.38038(10) 0.0277(7) Uani 1 1 d . . .
O5 O 0.0329(6) 0.4198(4) 0.35921(10) 0.0425(7) Uani 1 1 d . . .
C6 C 0.6720(7) 0.8772(5) 0.34206(11) 0.0259(7) Uani 1 1 d . . .
O7 O 0.9550(6) 0.7299(4) 0.26297(10) 0.0417(7) Uani 1 1 d . . .
N8 N 0.3212(6) 0.7256(4) 0.38326(10) 0.0288(7) Uani 1 1 d . . .
N9 N 0.2674(7) 1.0212(4) 0.44882(11) 0.0337(7) Uani 1 1 d . . .
N10 N 0.3265(7) 1.1840(4) 0.47058(11) 0.0342(7) Uani 1 1 d . . .
H10 H 0.2481 1.2310 0.4969 0.041 Uiso 1 1 d R . .
N11 N 0.2692(6) 0.4406(4) 0.34187(10) 0.0280(6) Uani 1 1 d . . .
N12 N 0.7320(6) 0.6514(4) 0.27471(10) 0.0303(7) Uani 1 1 d . . .
C13 C 0.4615(7) 1.0233(5) 0.41480(11) 0.0265(7) Uani 1 1 d . . .
N14 N 0.6289(7) 1.1746(5) 0.41525(11) 0.0377(8) Uani 1 1 d . . .
O15 O -0.1273(7) 0.6449(5) 0.45367(11) 0.0580(10) Uani 1 1 d . . .
H15A H -0.0155 0.6645 0.4310 0.070 Uiso 1 1 d R . .
H15B H -0.1820 0.5342 0.4496 0.070 Uiso 1 1 d R . .
N16 N 0.5345(7) 1.2767(5) 0.45164(11) 0.0395(8) Uani 1 1 d . . .
C17 C 0.6109(7) 0.7091(5) 0.31872(12) 0.0269(7) Uani 1 1 d . . .
C18 C 0.3951(7) 0.6254(5) 0.34608(12) 0.0265(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
O1 N11 1.220(4) . ?
O2 N12 1.224(4) . ?
N3 C6 1.339(4) . ?
N3 H3A 0.8901 . ?
N3 H3B 0.8901 . ?
N4 N8 1.377(4) . ?
N4 C6 1.381(4) . ?
N4 C13 1.398(4) . ?
O5 N11 1.232(4) . ?
C6 C17 1.397(5) . ?
O7 N12 1.243(4) . ?
N8 C18 1.309(4) . ?
N9 C13 1.325(4) . ?
N9 N10 1.342(4) . ?
N10 N16 1.302(5) . ?
N10 H10 0.8900 . ?
N11 C18 1.454(4) . ?
N12 C17 1.419(4) . ?
C13 N14 1.342(4) . ?
N14 N16 1.330(4) . ?
O15 H15A 0.8400 . ?
O15 H15B 0.8399 . ?
C17 C18 1.413(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N3 H3A 111.7 . . ?
C6 N3 H3B 110.1 . . ?
H3A N3 H3B 121.0 . . ?
N8 N4 C6 112.9(3) . . ?
N8 N4 C13 119.4(3) . . ?
C6 N4 C13 127.7(3) . . ?
N3 C6 N4 124.0(3) . . ?
N3 C6 C17 131.2(3) . . ?
N4 C6 C17 104.7(3) . . ?
C18 N8 N4 104.0(3) . . ?
C13 N9 N10 99.8(3) . . ?
N16 N10 N9 114.5(3) . . ?
N16 N10 H10 117.6 . . ?
N9 N10 H10 127.8 . . ?
O1 N11 O5 125.7(3) . . ?
O1 N11 C18 117.4(3) . . ?
O5 N11 C18 116.8(3) . . ?
O2 N12 O7 123.9(3) . . ?
O2 N12 C17 119.7(3) . . ?
O7 N12 C17 116.4(3) . . ?
N9 C13 N14 114.5(3) . . ?
N9 C13 N4 123.5(3) . . ?
N14 C13 N4 122.0(3) . . ?
N16 N14 C13 104.4(3) . . ?
H15A O15 H15B 104.5 . . ?
N10 N16 N14 106.8(3) . . ?
C6 C17 C18 105.2(3) . . ?
C6 C17 N12 124.7(3) . . ?
C18 C17 N12 129.9(3) . . ?
N8 C18 C17 113.2(3) . . ?
N8 C18 N11 116.7(3) . . ?
C17 C18 N11 129.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 N4 C6 N3 -177.7(3) . . . . ?
C13 N4 C6 N3 1.7(5) . . . . ?
N8 N4 C6 C17 1.5(4) . . . . ?
C13 N4 C6 C17 -179.1(3) . . . . ?
C6 N4 N8 C18 -1.5(4) . . . . ?
C13 N4 N8 C18 179.0(3) . . . . ?
C13 N9 N10 N16 0.3(4) . . . . ?
N10 N9 C13 N14 0.1(4) . . . . ?
N10 N9 C13 N4 -178.6(3) . . . . ?
N8 N4 C13 N9 -4.8(5) . . . . ?
C6 N4 C13 N9 175.8(3) . . . . ?
N8 N4 C13 N14 176.6(3) . . . . ?
C6 N4 C13 N14 -2.9(5) . . . . ?
N9 C13 N14 N16 -0.5(4) . . . . ?
N4 C13 N14 N16 178.3(3) . . . . ?
N9 N10 N16 N14 -0.6(4) . . . . ?
C13 N14 N16 N10 0.7(4) . . . . ?
N3 C6 C17 C18 178.3(3) . . . . ?
N4 C6 C17 C18 -0.8(4) . . . . ?
N3 C6 C17 N12 -6.4(6) . . . . ?
N4 C6 C17 N12 174.5(3) . . . . ?
O2 N12 C17 C6 -160.8(3) . . . . ?
O7 N12 C17 C6 19.4(5) . . . . ?
O2 N12 C17 C18 13.3(5) . . . . ?
O7 N12 C17 C18 -166.5(3) . . . . ?
N4 N8 C18 C17 0.9(4) . . . . ?
N4 N8 C18 N11 174.6(3) . . . . ?
C6 C17 C18 N8 0.0(4) . . . . ?
N12 C17 C18 N8 -175.0(3) . . . . ?
C6 C17 C18 N11 -172.7(3) . . . . ?
N12 C17 C18 N11 12.3(6) . . . . ?
O1 N11 C18 N8 -147.8(3) . . . . ?
O5 N11 C18 N8 29.2(4) . . . . ?
O1 N11 C18 C17 24.7(5) . . . . ?
O5 N11 C18 C17 -158.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.104
####################################################################### 
# 
# 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_bl80
_database_code_depnum_ccdc_archive 'CCDC 1449633'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H10 N10 O6'
_chemical_formula_weight         294.22

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           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   10.035(2)
_cell_length_b                   6.9626(14)
_cell_length_c                   16.699(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.60(3)
_cell_angle_gamma                90.00
_cell_volume                     1166.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3752
_cell_measurement_theta_min      2.0304
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7877
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2627
_reflns_number_gt                2338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0620P)²+0.5110P] 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         2627
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_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 0.17619(15) 0.2005(2) 0.78150(9) 0.0259(3) Uani 1 1 d . . .
O2 O 0.04506(16) 0.4473(2) 0.78036(9) 0.0321(4) Uani 1 1 d . . .
O3 O 0.37547(14) 0.2538(2) 0.67401(9) 0.0274(4) Uani 1 1 d . . .
O4 O 0.37158(14) 0.1306(2) 0.55365(9) 0.0284(4) Uani 1 1 d . . .
N1 N 0.10472(16) 0.3184(2) 0.74726(10) 0.0179(3) Uani 1 1 d . . .
N2 N 0.31482(16) 0.2021(2) 0.61235(10) 0.0197(4) Uani 1 1 d . . .
N3 N 0.13577(16) 0.1598(2) 0.45980(10) 0.0196(4) Uani 1 1 d . . .
H3A H 0.0790 0.1879 0.4196 0.024 Uiso 1 1 d R . .
H3B H 0.2204 0.1228 0.4568 0.024 Uiso 1 1 d R . .
N4 N -0.03271(15) 0.3308(2) 0.63042(9) 0.0160(3) Uani 1 1 d . . .
N5 N -0.02209(15) 0.2823(2) 0.55050(9) 0.0153(3) Uani 1 1 d . . .
N6 N -0.24808(15) 0.3787(2) 0.51686(10) 0.0192(4) Uani 1 1 d . . .
N7 N -0.31998(16) 0.3694(3) 0.44691(10) 0.0215(4) Uani 1 1 d . . .
N8 N -0.24797(17) 0.2934(3) 0.39125(10) 0.0227(4) Uani 1 1 d . . .
N9 N -0.12594(17) 0.2484(2) 0.42127(10) 0.0207(4) Uani 1 1 d . . .
C13 C -0.13182(18) 0.3028(3) 0.49735(11) 0.0154(4) Uani 1 1 d . . .
C17 C 0.08622(18) 0.2991(3) 0.66083(11) 0.0152(4) Uani 1 1 d . . .
C19 C 0.10298(18) 0.2167(3) 0.53207(11) 0.0151(4) Uani 1 1 d . . .
C20 C 0.17701(18) 0.2278(3) 0.60479(11) 0.0161(4) Uani 1 1 d . . .
O5 O 0.37330(14) 0.0263(2) 0.37808(9) 0.0248(3) Uani 1 1 d . . .
H5A H 0.3462 -0.0564 0.3448 0.030 Uiso 1 1 d R . .
H5B H 0.4355 -0.0347 0.4012 0.030 Uiso 1 1 d R . .
O6 O 0.71097(14) 0.2675(2) 0.72400(9) 0.0250(3) Uani 1 1 d . . .
H6A H 0.7199 0.2551 0.7739 0.030 Uiso 1 1 d R . .
H6B H 0.7832 0.3131 0.7083 0.030 Uiso 1 1 d R . .
N10 N 0.41538(16) 0.0729(3) 0.86902(10) 0.0216(4) Uani 1 1 d . . .
H10A H 0.3954 0.1952 0.8589 0.026 Uiso 1 1 d R . .
H10B H 0.4172 -0.0107 0.8287 0.026 Uiso 1 1 d R . .
H10C H 0.3584 0.0033 0.8968 0.026 Uiso 1 1 d R . .
H10D H 0.4941 0.0513 0.8932 0.026 Uiso 1 1 d R . .


_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 N1 1.222(2) . ?
O2 N1 1.220(2) . ?
O3 N2 1.235(2) . ?
O4 N2 1.251(2) . ?
N1 C17 1.456(2) . ?
N2 C20 1.397(2) . ?
N3 C19 1.321(2) . ?
N3 H3A 0.8899 . ?
N3 H3B 0.8900 . ?
N4 C17 1.303(2) . ?
N4 N5 1.384(2) . ?
N5 C19 1.378(2) . ?
N5 C13 1.402(2) . ?
N6 C13 1.329(2) . ?
N6 N7 1.357(2) . ?
N7 N8 1.305(2) . ?
N8 N9 1.347(2) . ?
N9 C13 1.329(2) . ?
C17 C20 1.414(3) . ?
C19 C20 1.408(3) . ?
O5 H5A 0.8402 . ?
O5 H5B 0.8401 . ?
O6 H6A 0.8400 . ?
O6 H6B 0.8399 . ?
N10 H10A 0.8900 . ?
N10 H10B 0.8901 . ?
N10 H10C 0.8900 . ?
N10 H10D 0.8899 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 124.87(17) . . ?
O2 N1 C17 117.79(16) . . ?
O1 N1 C17 117.31(16) . . ?
O3 N2 O4 123.02(16) . . ?
O3 N2 C20 120.11(17) . . ?
O4 N2 C20 116.84(16) . . ?
C19 N3 H3A 116.9 . . ?
C19 N3 H3B 113.6 . . ?
H3A N3 H3B 127.8 . . ?
C17 N4 N5 103.90(15) . . ?
C19 N5 N4 113.04(15) . . ?
C19 N5 C13 126.61(16) . . ?
N4 N5 C13 120.35(15) . . ?
C13 N6 N7 102.66(16) . . ?
N8 N7 N6 109.91(15) . . ?
N7 N8 N9 110.17(16) . . ?
C13 N9 N8 103.03(16) . . ?
N9 C13 N6 114.23(17) . . ?
N9 C13 N5 121.40(17) . . ?
N6 C13 N5 124.36(17) . . ?
N4 C17 C20 113.68(16) . . ?
N4 C17 N1 117.44(16) . . ?
C20 C17 N1 128.43(16) . . ?
N3 C19 N5 123.72(17) . . ?
N3 C19 C20 131.75(17) . . ?
N5 C19 C20 104.54(16) . . ?
N2 C20 C19 124.62(17) . . ?
N2 C20 C17 129.77(17) . . ?
C19 C20 C17 104.82(16) . . ?
H5A O5 H5B 100.3 . . ?
H6A O6 H6B 106.2 . . ?
H10A N10 H10B 119.4 . . ?
H10A N10 H10C 118.4 . . ?
H10B N10 H10C 93.7 . . ?
H10A N10 H10D 116.1 . . ?
H10B N10 H10D 101.3 . . ?
H10C N10 H10D 104.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N4 N5 C19 1.3(2) . . . . ?
C17 N4 N5 C13 -178.38(16) . . . . ?
C13 N6 N7 N8 -0.2(2) . . . . ?
N6 N7 N8 N9 0.1(2) . . . . ?
N7 N8 N9 C13 0.0(2) . . . . ?
N8 N9 C13 N6 -0.2(2) . . . . ?
N8 N9 C13 N5 -179.32(17) . . . . ?
N7 N6 C13 N9 0.2(2) . . . . ?
N7 N6 C13 N5 179.37(17) . . . . ?
C19 N5 C13 N9 3.7(3) . . . . ?
N4 N5 C13 N9 -176.67(17) . . . . ?
C19 N5 C13 N6 -175.36(19) . . . . ?
N4 N5 C13 N6 4.3(3) . . . . ?
N5 N4 C17 C20 -1.0(2) . . . . ?
N5 N4 C17 N1 -173.89(15) . . . . ?
O2 N1 C17 N4 -38.0(3) . . . . ?
O1 N1 C17 N4 140.02(18) . . . . ?
O2 N1 C17 C20 150.3(2) . . . . ?
O1 N1 C17 C20 -31.7(3) . . . . ?
N4 N5 C19 N3 179.09(17) . . . . ?
C13 N5 C19 N3 -1.3(3) . . . . ?
N4 N5 C19 C20 -1.1(2) . . . . ?
C13 N5 C19 C20 178.54(17) . . . . ?
O3 N2 C20 C19 164.51(18) . . . . ?
O4 N2 C20 C19 -13.6(3) . . . . ?
O3 N2 C20 C17 -3.8(3) . . . . ?
O4 N2 C20 C17 178.08(19) . . . . ?
N3 C19 C20 N2 9.5(3) . . . . ?
N5 C19 C20 N2 -170.26(17) . . . . ?
N3 C19 C20 C17 -179.7(2) . . . . ?
N5 C19 C20 C17 0.5(2) . . . . ?
N4 C17 C20 N2 170.39(19) . . . . ?
N1 C17 C20 N2 -17.6(3) . . . . ?
N4 C17 C20 C19 0.3(2) . . . . ?
N1 C17 C20 C19 172.31(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.110
####################################################################### 
# 
# 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_exp_3774
_database_code_depnum_ccdc_archive 'CCDC 1449638'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_audit_creation_date             2015-12-23
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H2 N9 O4, C H6 N3'
_chemical_formula_sum            'C5 H8 N12 O4'
_chemical_formula_weight         300.23
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y+1/2, z+1/2'
4 'x+1/2, -y+1/2, z'

_cell_length_a                   8.2623(7)
_cell_length_b                   24.641(2)
_cell_length_c                   5.6882(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1158.09(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    107.6
_cell_measurement_theta_max      29.4723
_cell_measurement_theta_min      2.9625
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4591
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      107.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00   46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   60.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -33.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -77.0000  150.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0621585000
_diffrn_orient_matrix_UB_12      -0.0174494000
_diffrn_orient_matrix_UB_13      0.0410321000
_diffrn_orient_matrix_UB_21      0.0114303000
_diffrn_orient_matrix_UB_22      0.0169847000
_diffrn_orient_matrix_UB_23      0.0993041000
_diffrn_orient_matrix_UB_31      -0.0581393000
_diffrn_orient_matrix_UB_32      -0.0153273000
_diffrn_orient_matrix_UB_33      0.0633037000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2021
_reflns_number_total             2159
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0339P)²+0.0461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0735
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N7 N -0.5281(2) -0.37019(7) -0.1805(3) 0.0183(4) Uani 1 1 d . . .
O2 O -0.40622(15) -0.47668(6) -0.4081(2) 0.0210(3) Uani 1 1 d . . .
N6 N -0.3536(2) -0.36556(6) 0.1456(3) 0.0160(4) Uani 1 1 d . . .
O4 O -0.62316(18) -0.39978(6) -0.2820(3) 0.0277(4) Uani 1 1 d . . .
O5 O -0.26496(17) -0.52959(6) -0.1803(3) 0.0239(3) Uani 1 1 d . . .
N5 N -0.24355(18) -0.39901(6) 0.2555(3) 0.0152(3) Uani 1 1 d . . .
N4 N -0.1766(2) -0.33067(7) 0.5393(3) 0.0200(4) Uani 1 1 d . . .
N8 N -0.33777(19) -0.48632(7) -0.2220(3) 0.0171(4) Uani 1 1 d . . .
O9 O -0.53061(18) -0.32016(6) -0.1898(3) 0.0276(4) Uani 1 1 d . . .
C5 C 0.1856(2) -0.30099(8) 0.2286(3) 0.0178(4) Uani 1 1 d . . .
N3 N -0.0793(2) -0.33097(7) 0.7310(3) 0.0214(4) Uani 1 1 d . . .
N2 N -0.0126(2) -0.37887(6) 0.7557(3) 0.0180(4) Uani 1 1 d . . .
N1 N -0.06399(19) -0.41217(7) 0.5813(3) 0.0175(4) Uani 1 1 d . . .
N9 N -0.1251(2) -0.48623(7) 0.2194(3) 0.0200(4) Uani 1 1 d . . .
H9A H -0.0638 -0.4804 0.3389 0.024 Uiso 1 1 calc R . .
H9B H -0.1197 -0.5167 0.1459 0.024 Uiso 1 1 calc R . .
C1 C -0.1629(2) -0.38053(8) 0.4575(3) 0.0151(4) Uani 1 1 d . . .
N10 N 0.1156(2) -0.26709(7) 0.0785(3) 0.0236(4) Uani 1 1 d . . .
H10A H 0.1192 -0.2327 0.1033 0.028 Uiso 1 1 calc R . .
H10B H 0.0666 -0.2795 -0.0435 0.028 Uiso 1 1 calc R . .
N12 N 0.2609(2) -0.28162(7) 0.4161(3) 0.0252(4) Uani 1 1 d . . .
H12A H 0.2643 -0.2472 0.4403 0.030 Uiso 1 1 calc R . .
H12B H 0.3064 -0.3035 0.5137 0.030 Uiso 1 1 calc R . .
N11 N 0.1814(2) -0.35413(7) 0.1897(3) 0.0203(4) Uani 1 1 d . . .
H11A H 0.2276 -0.3760 0.2864 0.024 Uiso 1 1 calc R . .
H11B H 0.1324 -0.3666 0.0677 0.024 Uiso 1 1 calc R . .
C2 C -0.2275(2) -0.44841(8) 0.1486(3) 0.0155(4) Uani 1 1 d . . .
C3 C -0.3319(2) -0.44641(8) -0.0444(3) 0.0151(4) Uani 1 1 d . . .
C4 C -0.4041(2) -0.39468(8) -0.0320(3) 0.0150(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
N7 O4 1.217(2) . ?
N7 O9 1.234(2) . ?
N7 C4 1.459(2) . ?
O2 N8 1.224(2) . ?
N6 N5 1.377(2) . ?
N6 C4 1.307(3) . ?
O5 N8 1.247(2) . ?
N5 C1 1.404(3) . ?
N5 C2 1.367(2) . ?
N4 N3 1.355(2) . ?
N4 C1 1.319(3) . ?
N8 C3 1.411(3) . ?
C5 N10 1.327(2) . ?
C5 N12 1.324(3) . ?
C5 N11 1.328(2) . ?
N3 N2 1.310(2) . ?
N2 N1 1.356(2) . ?
N1 C1 1.331(2) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N9 C2 1.322(2) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
C2 C3 1.397(3) . ?
C3 C4 1.409(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
O4 N7 O9 124.57(17) . . ?
O4 N7 C4 118.69(17) . . ?
O9 N7 C4 116.72(16) . . ?
C4 N6 N5 103.45(15) . . ?
N6 N5 C1 119.38(15) . . ?
C2 N5 N6 113.28(15) . . ?
C2 N5 C1 127.34(16) . . ?
C1 N4 N3 103.19(16) . . ?
O2 N8 O5 123.61(16) . . ?
O2 N8 C3 120.01(17) . . ?
O5 N8 C3 116.31(17) . . ?
N10 C5 N11 120.13(18) . . ?
N12 C5 N10 119.74(18) . . ?
N12 C5 N11 120.13(18) . . ?
N2 N3 N4 109.91(15) . . ?
N3 N2 N1 109.58(15) . . ?
C1 N1 N2 103.00(16) . . ?
H9A N9 H9B 120.0 . . ?
C2 N9 H9A 120.0 . . ?
C2 N9 H9B 120.0 . . ?
N4 C1 N5 123.38(17) . . ?
N4 C1 N1 114.31(17) . . ?
N1 C1 N5 122.30(18) . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C5 N12 H12A 120.0 . . ?
C5 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N5 C2 C3 104.97(16) . . ?
N9 C2 N5 123.67(17) . . ?
N9 C2 C3 131.26(19) . . ?
C2 C3 N8 124.03(18) . . ?
C2 C3 C4 104.70(17) . . ?
C4 C3 N8 130.68(18) . . ?
N6 C4 N7 116.39(17) . . ?
N6 C4 C3 113.59(17) . . ?
C3 C4 N7 129.99(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N8 C3 C2 -164.73(17) . . . . ?
O2 N8 C3 C4 5.1(3) . . . . ?
N6 N5 C1 N4 -5.7(3) . . . . ?
N6 N5 C1 N1 175.09(18) . . . . ?
N6 N5 C2 N9 177.77(17) . . . . ?
N6 N5 C2 C3 1.0(2) . . . . ?
O4 N7 C4 N6 -151.03(17) . . . . ?
O4 N7 C4 C3 26.6(3) . . . . ?
O5 N8 C3 C2 12.4(3) . . . . ?
O5 N8 C3 C4 -177.73(18) . . . . ?
N5 N6 C4 N7 178.13(16) . . . . ?
N5 N6 C4 C3 0.1(2) . . . . ?
N5 C2 C3 N8 171.24(17) . . . . ?
N5 C2 C3 C4 -0.80(19) . . . . ?
N4 N3 N2 N1 -0.3(2) . . . . ?
N8 C3 C4 N7 11.5(3) . . . . ?
N8 C3 C4 N6 -170.86(19) . . . . ?
O9 N7 C4 N6 27.5(3) . . . . ?
O9 N7 C4 C3 -154.87(19) . . . . ?
N3 N4 C1 N5 -179.67(17) . . . . ?
N3 N4 C1 N1 -0.4(2) . . . . ?
N3 N2 N1 C1 0.0(2) . . . . ?
N2 N1 C1 N5 179.53(16) . . . . ?
N2 N1 C1 N4 0.3(2) . . . . ?
N9 C2 C3 N8 -5.2(3) . . . . ?
N9 C2 C3 C4 -177.3(2) . . . . ?
C1 N5 C2 N9 -2.7(3) . . . . ?
C1 N5 C2 C3 -179.53(17) . . . . ?
C1 N4 N3 N2 0.4(2) . . . . ?
C2 N5 C1 N4 174.80(18) . . . . ?
C2 N5 C1 N1 -4.4(3) . . . . ?
C2 C3 C4 N7 -177.23(19) . . . . ?
C2 C3 C4 N6 0.4(2) . . . . ?
C4 N6 N5 C1 179.76(15) . . . . ?
C4 N6 N5 C2 -0.7(2) . . . . ?

####################################################################### 
# 
# 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_exp_4288
_database_code_depnum_ccdc_archive 'CCDC 1489506'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_audit_creation_date             2016-06-29
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H6 N9 Na O6'
_chemical_formula_sum            'C4 H6 N9 Na O6'
_chemical_formula_weight         299.17
_chemical_melting_point          ?
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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.2793(5)
_cell_length_b                   5.8543(2)
_cell_length_c                   20.6029(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.757(4)
_cell_angle_gamma                90.00
_cell_volume                     1099.55(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1703
_cell_measurement_temperature    106.2
_cell_measurement_theta_max      29.2706
_cell_measurement_theta_min      3.2684
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4654
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.27
_diffrn_ambient_temperature      106.2
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    5.00   40.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.9711   77.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega    9.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1273   77.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1273   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
  4 omega   53.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1273   77.0000  -30.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0735739000
_diffrn_orient_matrix_UB_12      -0.0391985000
_diffrn_orient_matrix_UB_13      -0.0043546000
_diffrn_orient_matrix_UB_21      0.0252030000
_diffrn_orient_matrix_UB_22      -0.1101245000
_diffrn_orient_matrix_UB_23      0.0110127000
_diffrn_orient_matrix_UB_31      -0.0026013000
_diffrn_orient_matrix_UB_32      0.0315989000
_diffrn_orient_matrix_UB_33      0.0330004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1849
_reflns_number_total             2168
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.4304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0815
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Na1 Na 0.13468(7) 0.80004(12) -0.01073(3) 0.01558(18) Uani 1 1 d . . .
O6 O 0.11845(12) 1.1255(2) 0.05661(6) 0.0161(3) Uani 1 1 d . . .
H6A H 0.1752 1.2365 0.0536 0.024 Uiso 1 1 d R . .
H6B H 0.1312 1.0880 0.0968 0.024 Uiso 1 1 d R . .
N9 N 0.02334(14) 0.3152(2) -0.12916(7) 0.0138(3) Uani 1 1 d . . .
O1 O 0.26903(13) 0.2949(2) -0.30200(6) 0.0187(3) Uani 1 1 d . . .
N1 N 0.30699(14) 1.0301(2) -0.06993(7) 0.0137(3) Uani 1 1 d . . .
N5 N 0.27715(14) 0.7328(2) -0.15006(7) 0.0119(3) Uani 1 1 d . . .
O3 O -0.03834(14) 0.1625(2) -0.16352(6) 0.0246(3) Uani 1 1 d . . .
O2 O 0.13016(13) 0.0791(2) -0.25345(7) 0.0236(3) Uani 1 1 d . . .
O4 O 0.00029(13) 0.3648(2) -0.07411(6) 0.0199(3) Uani 1 1 d . . .
N2 N 0.39684(15) 1.2130(2) -0.05929(7) 0.0150(3) Uani 1 1 d . . .
N8 N 0.19829(15) 0.2571(3) -0.25708(7) 0.0145(3) Uani 1 1 d . . .
N6 N 0.17570(14) 0.6328(2) -0.11867(7) 0.0121(3) Uani 1 1 d . . .
N7 N 0.39003(15) 0.6847(3) -0.24273(7) 0.0171(3) Uani 1 1 d . . .
H7A H 0.4427 0.8089 -0.2324 0.021 Uiso 1 1 calc R . .
H7B H 0.3994 0.6052 -0.2780 0.021 Uiso 1 1 calc R . .
N4 N 0.45107(15) 1.0401(3) -0.14557(7) 0.0145(3) Uani 1 1 d . . .
N3 N 0.48098(15) 1.2204(3) -0.10382(7) 0.0153(3) Uani 1 1 d . . .
C4 C 0.13345(17) 0.4516(3) -0.15366(8) 0.0116(4) Uani 1 1 d . . .
C1 C 0.34487(17) 0.9330(3) -0.12246(8) 0.0113(3) Uani 1 1 d . . .
C3 C 0.20293(17) 0.4276(3) -0.20879(8) 0.0116(4) Uani 1 1 d . . .
C2 C 0.29668(17) 0.6173(3) -0.20521(8) 0.0125(4) Uani 1 1 d . . .
O5 O 0.29107(12) 0.4949(2) 0.03470(6) 0.0165(3) Uani 1 1 d . . .
H5A H 0.3533 0.5576 0.0647 0.025 Uiso 1 1 d R . .
H5B H 0.3340 0.4258 0.0077 0.025 Uiso 1 1 d R . .


_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
Na1 Na1 3.5124(13) 3_575 ?
Na1 O6 2.4025(13) 3_575 ?
Na1 O6 2.3782(14) . ?
Na1 N1 2.5663(16) . ?
Na1 O4 2.5244(14) 3_565 ?
Na1 N6 2.5228(16) . ?
Na1 O5 2.3802(14) . ?
O6 Na1 2.4025(13) 3_575 ?
O6 H6A 0.8459 . ?
O6 H6B 0.8440 . ?
N9 O3 1.2151(18) . ?
N9 O4 1.2276(19) . ?
N9 C4 1.459(2) . ?
O1 N8 1.2502(19) . ?
N1 N2 1.3496(19) . ?
N1 C1 1.327(2) . ?
N5 N6 1.3690(19) . ?
N5 C1 1.400(2) . ?
N5 C2 1.363(2) . ?
O2 N8 1.2284(19) . ?
O4 Na1 2.5244(14) 3_565 ?
N2 N3 1.312(2) . ?
N8 C3 1.404(2) . ?
N6 C4 1.301(2) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C2 1.324(2) . ?
N4 N3 1.357(2) . ?
N4 C1 1.329(2) . ?
C4 C3 1.414(2) . ?
C3 C2 1.404(2) . ?
O5 H5A 0.8464 . ?
O5 H5B 0.8450 . ?

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
O6 Na1 Na1 42.45(3) 3_575 3_575 ?
O6 Na1 Na1 42.99(3) . 3_575 ?
O6 Na1 O6 85.44(5) . 3_575 ?
O6 Na1 N1 88.27(5) . . ?
O6 Na1 N1 111.58(5) 3_575 . ?
O6 Na1 O4 76.52(4) 3_575 3_565 ?
O6 Na1 O4 78.97(4) . 3_565 ?
O6 Na1 N6 91.19(5) 3_575 . ?
O6 Na1 N6 149.49(5) . . ?
O6 Na1 O5 118.17(5) . . ?
N1 Na1 Na1 103.36(4) . 3_575 ?
O4 Na1 Na1 73.20(4) 3_565 3_575 ?
O4 Na1 N1 164.44(5) 3_565 . ?
N6 Na1 Na1 126.70(5) . 3_575 ?
N6 Na1 N1 64.84(5) . . ?
N6 Na1 O4 129.65(5) . 3_565 ?
O5 Na1 Na1 147.85(5) . 3_575 ?
O5 Na1 O6 140.39(5) . 3_575 ?
O5 Na1 N1 101.10(5) . . ?
O5 Na1 O4 77.63(5) . 3_565 ?
O5 Na1 N6 82.78(5) . . ?
Na1 O6 Na1 94.56(5) . 3_575 ?
Na1 O6 H6A 114.1 3_575 . ?
Na1 O6 H6A 117.7 . . ?
Na1 O6 H6B 112.4 3_575 . ?
Na1 O6 H6B 110.6 . . ?
H6A O6 H6B 107.3 . . ?
O3 N9 O4 124.61(15) . . ?
O3 N9 C4 119.03(14) . . ?
O4 N9 C4 116.36(14) . . ?
N2 N1 Na1 139.46(11) . . ?
C1 N1 Na1 116.51(11) . . ?
C1 N1 N2 102.86(13) . . ?
N6 N5 C1 117.54(13) . . ?
C2 N5 N6 113.08(14) . . ?
C2 N5 C1 129.38(14) . . ?
N9 O4 Na1 138.06(11) . 3_565 ?
N3 N2 N1 110.06(14) . . ?
O1 N8 C3 116.61(14) . . ?
O2 N8 O1 122.86(15) . . ?
O2 N8 C3 120.51(15) . . ?
N5 N6 Na1 118.73(10) . . ?
C4 N6 Na1 136.49(11) . . ?
C4 N6 N5 104.44(13) . . ?
H7A N7 H7B 120.0 . . ?
C2 N7 H7A 120.0 . . ?
C2 N7 H7B 120.0 . . ?
C1 N4 N3 102.56(14) . . ?
N2 N3 N4 109.85(13) . . ?
N6 C4 N9 114.37(15) . . ?
N6 C4 C3 113.01(14) . . ?
C3 C4 N9 132.61(15) . . ?
N1 C1 N5 121.53(14) . . ?
N1 C1 N4 114.66(15) . . ?
N4 C1 N5 123.81(15) . . ?
N8 C3 C4 132.99(15) . . ?
N8 C3 C2 122.41(15) . . ?
C2 C3 C4 104.48(14) . . ?
N5 C2 C3 104.98(14) . . ?
N7 C2 N5 122.84(16) . . ?
N7 C2 C3 132.17(16) . . ?
Na1 O5 H5A 104.1 . . ?
Na1 O5 H5B 115.3 . . ?
H5A O5 H5B 110.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 Na1 N1 N2 62.46(16) 3_575 . . . ?
Na1 Na1 N1 C1 -132.50(11) 3_575 . . . ?
Na1 Na1 N6 N5 94.53(11) 3_575 . . . ?
Na1 Na1 N6 C4 -93.31(16) 3_575 . . . ?
Na1 N1 N2 N3 166.68(12) . . . . ?
Na1 N1 C1 N5 9.51(19) . . . . ?
Na1 N1 C1 N4 -170.08(11) . . . . ?
Na1 N6 C4 N9 7.1(2) . . . . ?
Na1 N6 C4 C3 -173.61(11) . . . . ?
O6 Na1 O6 Na1 0.0 3_575 . . 3_575 ?
O6 Na1 N1 N2 106.27(16) 3_575 . . . ?
O6 Na1 N1 N2 21.87(16) . . . . ?
O6 Na1 N1 C1 -173.09(12) . . . . ?
O6 Na1 N1 C1 -88.69(12) 3_575 . . . ?
O6 Na1 N6 N5 119.72(11) 3_575 . . . ?
O6 Na1 N6 N5 36.69(16) . . . . ?
O6 Na1 N6 C4 -68.12(16) 3_575 . . . ?
O6 Na1 N6 C4 -151.15(14) . . . . ?
N9 C4 C3 N8 -4.9(3) . . . . ?
N9 C4 C3 C2 179.24(16) . . . . ?
O1 N8 C3 C4 176.46(16) . . . . ?
O1 N8 C3 C2 -8.3(2) . . . . ?
N1 Na1 O6 Na1 111.82(5) . . . 3_575 ?
N1 Na1 N6 N5 6.34(10) . . . . ?
N1 Na1 N6 C4 178.50(17) . . . . ?
N1 N2 N3 N4 -0.65(18) . . . . ?
N5 N6 C4 N9 179.97(13) . . . . ?
N5 N6 C4 C3 -0.70(18) . . . . ?
O3 N9 O4 Na1 10.5(3) . . . 3_565 ?
O3 N9 C4 N6 169.33(14) . . . . ?
O3 N9 C4 C3 -9.8(3) . . . . ?
O2 N8 C3 C4 -5.1(3) . . . . ?
O2 N8 C3 C2 170.12(15) . . . . ?
O4 Na1 O6 Na1 -77.13(4) 3_565 . . 3_575 ?
O4 Na1 N1 N2 -12.8(3) 3_565 . . . ?
O4 Na1 N1 C1 152.24(18) 3_565 . . . ?
O4 Na1 N6 N5 -166.88(10) 3_565 . . . ?
O4 Na1 N6 C4 5.28(19) 3_565 . . . ?
O4 N9 C4 N6 -10.9(2) . . . . ?
O4 N9 C4 C3 169.98(16) . . . . ?
N2 N1 C1 N5 179.60(14) . . . . ?
N2 N1 C1 N4 0.01(19) . . . . ?
N8 C3 C2 N5 -175.84(14) . . . . ?
N8 C3 C2 N7 2.8(3) . . . . ?
N6 Na1 O6 Na1 84.59(10) . . . 3_575 ?
N6 Na1 N1 N2 -173.00(17) . . . . ?
N6 Na1 N1 C1 -7.96(11) . . . . ?
N6 N5 C1 N1 -3.6(2) . . . . ?
N6 N5 C1 N4 175.97(15) . . . . ?
N6 N5 C2 N7 -179.85(14) . . . . ?
N6 N5 C2 C3 -1.08(18) . . . . ?
N6 C4 C3 N8 175.95(16) . . . . ?
N6 C4 C3 C2 0.08(18) . . . . ?
N3 N4 C1 N1 -0.38(19) . . . . ?
N3 N4 C1 N5 -179.96(15) . . . . ?
C4 N9 O4 Na1 -169.28(11) . . . 3_565 ?
C4 C3 C2 N5 0.59(17) . . . . ?
C4 C3 C2 N7 179.19(17) . . . . ?
C1 N1 N2 N3 0.39(17) . . . . ?
C1 N5 N6 Na1 -4.49(18) . . . . ?
C1 N5 N6 C4 -178.93(14) . . . . ?
C1 N5 C2 N7 0.2(3) . . . . ?
C1 N5 C2 C3 178.98(15) . . . . ?
C1 N4 N3 N2 0.61(17) . . . . ?
C2 N5 N6 Na1 175.56(10) . . . . ?
C2 N5 N6 C4 1.12(18) . . . . ?
C2 N5 C1 N1 176.36(16) . . . . ?
C2 N5 C1 N4 -4.1(3) . . . . ?
O5 Na1 O6 Na1 -146.51(5) . . . 3_575 ?
O5 Na1 N1 N2 -96.52(16) . . . . ?
O5 Na1 N1 C1 68.53(12) . . . . ?
O5 Na1 N6 N5 -99.56(11) . . . . ?
O5 Na1 N6 C4 72.61(16) . . . . ?

