# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1031121'
_audit_update_record             
;
2014-10-27 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 N6 Na O8'
_chemical_formula_weight         314.17

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'
Na Na 0.0362 0.0249 '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                   13.087(3)
_cell_length_b                   13.021(3)
_cell_length_c                   6.3070(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.56(3)
_cell_angle_gamma                90.00
_cell_volume                     1074.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_process_details   'SADABS,2000; Bruker'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1974
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0862
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.39
_reflns_number_total             1974
_reflns_number_gt                1181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1036P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1974
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2030
_refine_ls_wR_factor_gt          0.1752
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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
Na1 Na -0.04754(15) 0.07917(19) 0.2550(3) 0.0544(7) Uani 1 1 d . . .
N1 N 0.3908(3) -0.1824(3) 0.1933(7) 0.0397(10) Uani 1 1 d . . .
C1 C 0.1949(3) 0.0144(3) 0.1268(7) 0.0319(10) Uani 1 1 d . . .
N3 N 0.1024(2) 0.0083(2) 0.0874(6) 0.0241(8) Uani 1 1 d . . .
H3B H 0.0756 -0.0509 0.0631 0.029 Uiso 1 1 d R . .
C2 C 0.2534(3) 0.1051(3) 0.1718(7) 0.0294(10) Uani 1 1 d . . .
N2 N 0.2209(3) -0.1723(3) 0.1018(6) 0.0365(10) Uani 1 1 d . . .
O1 O 0.1056(2) 0.1977(3) 0.1781(7) 0.0568(12) Uani 1 1 d . . .
N4 N 0.1992(3) 0.1991(3) 0.1668(6) 0.0296(9) Uani 1 1 d . . .
C3 C 0.3635(3) 0.1057(3) 0.2090(7) 0.0285(10) Uani 1 1 d . . .
O2 O 0.0125(3) 0.1077(3) 0.6062(6) 0.0478(10) Uani 1 1 d . . .
H2B H 0.0448 0.0573 0.6603 0.072 Uiso 1 1 d R . .
H2A H 0.0214 0.1646 0.6700 0.072 Uiso 1 1 d R . .
N5 N 0.4133(3) 0.1909(3) 0.2352(6) 0.0362(10) Uani 1 1 d . . .
H5A H 0.3813 0.2486 0.2307 0.043 Uiso 1 1 calc R . .
H5B H 0.4782 0.1898 0.2570 0.043 Uiso 1 1 calc R . .
C4 C 0.4160(3) 0.0068(3) 0.2266(8) 0.0318(11) Uani 1 1 d . . .
O3 O -0.2121(3) 0.0258(3) 0.3587(6) 0.0518(10) Uani 1 1 d . . .
H3D H -0.2609 0.0580 0.2989 0.078 Uiso 1 1 d R . .
H3C H -0.2161 -0.0370 0.3535 0.078 Uiso 1 1 d R . .
O4 O 0.2434(3) 0.2830(2) 0.1520(6) 0.0435(9) Uani 1 1 d . . .
N6 N 0.5214(3) 0.0003(3) 0.2618(6) 0.0344(9) Uani 1 1 d . . .
C5 C 0.3612(3) -0.0863(3) 0.1868(8) 0.0321(11) Uani 1 1 d . . .
O5 O 0.5746(2) 0.0794(2) 0.2944(5) 0.0389(8) Uani 1 1 d . . .
C6 C 0.2563(3) -0.0790(3) 0.1408(7) 0.0334(11) Uani 1 1 d . . .
O6 O 0.5600(3) -0.0856(3) 0.2753(6) 0.0437(9) Uani 1 1 d . . .
O7 O 0.3043(3) -0.2410(3) 0.1411(6) 0.0468(10) Uani 1 1 d . . .
O8 O 0.1378(3) -0.2102(3) 0.0546(7) 0.0528(11) 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
Na1 O3 2.361(4) . ?
Na1 O2 2.372(4) . ?
Na1 N3 2.421(4) . ?
Na1 N3 2.539(4) 3 ?
Na1 O1 2.579(4) . ?
Na1 O2 2.625(4) 3_556 ?
Na1 O8 2.842(4) 3 ?
Na1 Na1 3.908(5) 3_556 ?
Na1 Na1 4.028(5) 3 ?
Na1 H3B 2.6400 . ?
N1 C5 1.311(6) . ?
N1 O7 1.402(5) . ?
C1 N3 1.236(5) . ?
C1 C2 1.435(6) . ?
C1 C6 1.459(6) . ?
N3 Na1 2.539(4) 3 ?
N3 H3B 0.8600 . ?
C2 N4 1.414(5) . ?
C2 C3 1.458(6) . ?
N2 O8 1.229(5) . ?
N2 C6 1.322(6) . ?
N2 O7 1.431(5) . ?
O1 N4 1.228(5) . ?
N4 O4 1.241(5) . ?
C3 N5 1.296(5) . ?
C3 C4 1.464(6) . ?
O2 Na1 2.625(4) 3_556 ?
O2 H2B 0.8500 . ?
O2 H2A 0.8501 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
C4 N6 1.398(5) . ?
C4 C5 1.429(6) . ?
O3 H3D 0.8501 . ?
O3 H3C 0.8199 . ?
N6 O6 1.230(5) . ?
N6 O5 1.259(4) . ?
C5 C6 1.403(6) . ?
O8 Na1 2.842(4) 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
O3 Na1 O2 94.71(15) . . ?
O3 Na1 N3 138.94(16) . . ?
O2 Na1 N3 101.82(14) . . ?
O3 Na1 N3 81.52(13) . 3 ?
O2 Na1 N3 162.32(16) . 3 ?
N3 Na1 N3 71.41(14) . 3 ?
O3 Na1 O1 160.14(17) . . ?
O2 Na1 O1 80.27(14) . . ?
N3 Na1 O1 60.76(13) . . ?
N3 Na1 O1 108.80(14) 3 . ?
O3 Na1 O2 77.97(13) . 3_556 ?
O2 Na1 O2 77.21(14) . 3_556 ?
N3 Na1 O2 69.67(13) . 3_556 ?
N3 Na1 O2 85.11(13) 3 3_556 ?
O1 Na1 O2 118.96(13) . 3_556 ?
O3 Na1 O8 89.60(13) . 3 ?
O2 Na1 O8 132.78(15) . 3 ?
N3 Na1 O8 105.20(14) . 3 ?
N3 Na1 O8 64.71(12) 3 3 ?
O1 Na1 O8 80.20(13) . 3 ?
O2 Na1 O8 148.86(13) 3_556 3 ?
O3 Na1 Na1 84.83(12) . 3_556 ?
O2 Na1 Na1 40.91(9) . 3_556 ?
N3 Na1 Na1 83.74(11) . 3_556 ?
N3 Na1 Na1 121.41(13) 3 3_556 ?
O1 Na1 Na1 102.86(12) . 3_556 ?
O2 Na1 Na1 36.30(9) 3_556 3_556 ?
O8 Na1 Na1 170.80(14) 3 3_556 ?
O3 Na1 Na1 111.12(13) . 3 ?
O2 Na1 Na1 136.36(14) . 3 ?
N3 Na1 Na1 36.68(9) . 3 ?
N3 Na1 Na1 34.72(8) 3 3 ?
O1 Na1 Na1 84.81(12) . 3 ?
O2 Na1 Na1 74.78(11) 3_556 3 ?
O8 Na1 Na1 83.58(11) 3 3 ?
Na1 Na1 Na1 105.25(11) 3_556 3 ?
O3 Na1 H3B 120.0 . . ?
O2 Na1 H3B 109.3 . . ?
N3 Na1 H3B 18.9 . . ?
N3 Na1 H3B 59.4 3 . ?
O1 Na1 H3B 79.6 . . ?
O2 Na1 H3B 56.8 3_556 . ?
O8 Na1 H3B 108.8 3 . ?
Na1 Na1 H3B 80.4 3_556 . ?
Na1 Na1 H3B 27.2 3 . ?
C5 N1 O7 105.9(4) . . ?
N3 C1 C2 127.7(4) . . ?
N3 C1 C6 119.8(4) . . ?
C2 C1 C6 112.5(4) . . ?
C1 N3 Na1 133.2(3) . . ?
C1 N3 Na1 117.9(3) . 3 ?
Na1 N3 Na1 108.59(14) . 3 ?
C1 N3 H3B 119.3 . . ?
Na1 N3 H3B 95.1 . . ?
Na1 N3 H3B 48.3 3 . ?
N4 C2 C1 116.2(4) . . ?
N4 C2 C3 119.6(4) . . ?
C1 C2 C3 124.1(4) . . ?
O8 N2 C6 136.2(4) . . ?
O8 N2 O7 117.5(3) . . ?
C6 N2 O7 106.1(3) . . ?
N4 O1 Na1 142.9(3) . . ?
O1 N4 O4 118.9(4) . . ?
O1 N4 C2 119.1(4) . . ?
O4 N4 C2 122.0(4) . . ?
N5 C3 C2 121.3(4) . . ?
N5 C3 C4 120.6(4) . . ?
C2 C3 C4 118.0(4) . . ?
Na1 O2 Na1 102.79(14) . 3_556 ?
Na1 O2 H2B 114.4 . . ?
Na1 O2 H2B 20.9 3_556 . ?
Na1 O2 H2A 128.4 . . ?
Na1 O2 H2A 128.8 3_556 . ?
H2B O2 H2A 114.7 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N6 C4 C5 118.0(4) . . ?
N6 C4 C3 121.8(4) . . ?
C5 C4 C3 119.9(4) . . ?
Na1 O3 H3D 114.6 . . ?
Na1 O3 H3C 109.9 . . ?
H3D O3 H3C 115.2 . . ?
O6 N6 O5 120.4(4) . . ?
O6 N6 C4 118.0(4) . . ?
O5 N6 C4 121.4(4) . . ?
N1 C5 C6 111.1(4) . . ?
N1 C5 C4 131.0(4) . . ?
C6 C5 C4 117.9(4) . . ?
N2 C6 C5 108.4(4) . . ?
N2 C6 C1 124.2(4) . . ?
C5 C6 C1 127.3(4) . . ?
N1 O7 N2 108.2(3) . . ?
N2 O8 Na1 106.6(3) . 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
C2 C1 N3 Na1 -48.0(7) . . . . ?
C6 C1 N3 Na1 129.1(4) . . . . ?
C2 C1 N3 Na1 124.6(5) . . . 3 ?
C6 C1 N3 Na1 -58.3(5) . . . 3 ?
O3 Na1 N3 C1 -135.4(4) . . . . ?
O2 Na1 N3 C1 -23.8(4) . . . . ?
N3 Na1 N3 C1 173.1(5) 3 . . . ?
O1 Na1 N3 C1 47.8(4) . . . . ?
O2 Na1 N3 C1 -95.2(4) 3_556 . . . ?
O8 Na1 N3 C1 117.1(4) 3 . . . ?
Na1 Na1 N3 C1 -60.7(4) 3_556 . . . ?
Na1 Na1 N3 C1 173.1(5) 3 . . . ?
O3 Na1 N3 Na1 51.5(3) . . . 3 ?
O2 Na1 N3 Na1 163.06(16) . . . 3 ?
N3 Na1 N3 Na1 0.0 3 . . 3 ?
O1 Na1 N3 Na1 -125.31(18) . . . 3 ?
O2 Na1 N3 Na1 91.65(14) 3_556 . . 3 ?
O8 Na1 N3 Na1 -56.05(15) 3 . . 3 ?
Na1 Na1 N3 Na1 126.16(14) 3_556 . . 3 ?
N3 C1 C2 N4 -1.2(7) . . . . ?
C6 C1 C2 N4 -178.5(4) . . . . ?
N3 C1 C2 C3 -177.6(4) . . . . ?
C6 C1 C2 C3 5.1(7) . . . . ?
O3 Na1 O1 N4 153.6(5) . . . . ?
O2 Na1 O1 N4 76.9(6) . . . . ?
N3 Na1 O1 N4 -32.6(5) . . . . ?
N3 Na1 O1 N4 -87.4(6) 3 . . . ?
O2 Na1 O1 N4 7.5(6) 3_556 . . . ?
O8 Na1 O1 N4 -146.3(6) 3 . . . ?
Na1 Na1 O1 N4 42.6(6) 3_556 . . . ?
Na1 Na1 O1 N4 -61.9(6) 3 . . . ?
Na1 O1 N4 O4 -169.5(4) . . . . ?
Na1 O1 N4 C2 10.2(8) . . . . ?
C1 C2 N4 O1 17.9(6) . . . . ?
C3 C2 N4 O1 -165.5(4) . . . . ?
C1 C2 N4 O4 -162.4(4) . . . . ?
C3 C2 N4 O4 14.2(6) . . . . ?
N4 C2 C3 N5 -0.9(7) . . . . ?
C1 C2 C3 N5 175.4(4) . . . . ?
N4 C2 C3 C4 176.2(4) . . . . ?
C1 C2 C3 C4 -7.5(7) . . . . ?
O3 Na1 O2 Na1 76.51(15) . . . 3_556 ?
N3 Na1 O2 Na1 -65.70(15) . . . 3_556 ?
N3 Na1 O2 Na1 -0.3(5) 3 . . 3_556 ?
O1 Na1 O2 Na1 -122.86(15) . . . 3_556 ?
O2 Na1 O2 Na1 0.0 3_556 . . 3_556 ?
O8 Na1 O2 Na1 170.34(18) 3 . . 3_556 ?
Na1 Na1 O2 Na1 -51.1(2) 3 . . 3_556 ?
N5 C3 C4 N6 -3.0(7) . . . . ?
C2 C3 C4 N6 179.9(4) . . . . ?
N5 C3 C4 C5 -176.8(5) . . . . ?
C2 C3 C4 C5 6.1(7) . . . . ?
C5 C4 N6 O6 -6.3(7) . . . . ?
C3 C4 N6 O6 179.8(5) . . . . ?
C5 C4 N6 O5 178.8(4) . . . . ?
C3 C4 N6 O5 4.9(7) . . . . ?
O7 N1 C5 C6 2.5(5) . . . . ?
O7 N1 C5 C4 179.6(5) . . . . ?
N6 C4 C5 N1 6.3(8) . . . . ?
C3 C4 C5 N1 -179.7(5) . . . . ?
N6 C4 C5 C6 -176.8(4) . . . . ?
C3 C4 C5 C6 -2.8(7) . . . . ?
O8 N2 C6 C5 -180.0(5) . . . . ?
O7 N2 C6 C5 4.6(5) . . . . ?
O8 N2 C6 C1 -2.6(9) . . . . ?
O7 N2 C6 C1 -178.0(4) . . . . ?
N1 C5 C6 N2 -4.7(6) . . . . ?
C4 C5 C6 N2 177.8(4) . . . . ?
N1 C5 C6 C1 178.0(5) . . . . ?
C4 C5 C6 C1 0.5(8) . . . . ?
N3 C1 C6 N2 4.1(7) . . . . ?
C2 C1 C6 N2 -178.4(5) . . . . ?
N3 C1 C6 C5 -179.0(5) . . . . ?
C2 C1 C6 C5 -1.5(7) . . . . ?
C5 N1 O7 N2 0.4(5) . . . . ?
O8 N2 O7 N1 -179.6(4) . . . . ?
C6 N2 O7 N1 -3.2(5) . . . . ?
C6 N2 O8 Na1 42.6(7) . . . 3 ?
O7 N2 O8 Na1 -142.4(3) . . . 3 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.090
