# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc1mh47h
_database_code_depnum_ccdc_archive 'CCDC 1504096'
_audit_update_record             
;
2016-09-13 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 N6 O4'
_chemical_formula_weight         284.29

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   C2/c

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

_cell_length_a                   21.477(3)
_cell_length_b                   10.2253(14)
_cell_length_c                   12.3312(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.717(3)
_cell_angle_gamma                90.00
_cell_volume                     2676.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    823
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.65

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_process_details   'SADABS (SHELDRICK, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7250
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2351
_reflns_number_gt                2024
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0733P)²+0.6372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2351
_refine_ls_number_parameters     197
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23533(6) 0.91352(13) 0.01828(11) 0.0444(3) Uani 1 1 d . . .
C2 C 0.30499(6) 0.92831(13) 0.05514(11) 0.0435(3) Uani 1 1 d . . .
C3 C 0.34512(7) 0.95400(16) -0.01965(13) 0.0563(4) Uani 1 1 d . . .
H3 H 0.3293 0.9595 -0.0940 0.068 Uiso 1 1 calc R . .
C4 C 0.40901(7) 0.97172(18) 0.01595(15) 0.0653(5) Uani 1 1 d . . .
H4 H 0.4358 0.9893 -0.0348 0.078 Uiso 1 1 calc R . .
C5 C 0.43263(7) 0.96358(18) 0.12436(15) 0.0656(5) Uani 1 1 d . . .
H5 H 0.4753 0.9774 0.1480 0.079 Uiso 1 1 calc R . .
C6 C 0.39318(8) 0.9348(2) 0.19901(15) 0.0702(5) Uani 1 1 d . . .
H6 H 0.4095 0.9268 0.2730 0.084 Uiso 1 1 calc R . .
C7 C 0.32950(7) 0.91780(16) 0.16463(13) 0.0566(4) Uani 1 1 d . . .
H7 H 0.3030 0.8991 0.2157 0.068 Uiso 1 1 calc R . .
C8 C 0.04671(6) 0.86417(12) -0.07952(11) 0.0396(3) Uani 1 1 d . . .
C9 C 0.04721(6) 0.82262(13) 0.10748(10) 0.0414(3) Uani 1 1 d . . .
C10 C -0.04364(6) 0.81810(12) -0.01273(11) 0.0395(3) Uani 1 1 d . . .
N1 N 0.07862(5) 0.85544(11) 0.02436(9) 0.0421(3) Uani 1 1 d D . .
H1 H 0.1184 0.8707 0.0370 0.050 Uiso 1 1 calc RD . .
N2 N -0.01447(5) 0.80314(11) 0.09147(9) 0.0427(3) Uani 1 1 d . . .
N3 N -0.01532(5) 0.84673(11) -0.10047(9) 0.0422(3) Uani 1 1 d . . .
N4 N 0.07994(5) 0.81054(14) 0.20610(10) 0.0564(4) Uani 1 1 d . . .
H4A H 0.0613 0.7899 0.2607 0.068 Uiso 1 1 calc R . .
H4B H 0.1200 0.8233 0.2160 0.068 Uiso 1 1 calc R . .
N5 N -0.10543(5) 0.80279(12) -0.03005(10) 0.0495(3) Uani 1 1 d . . .
H5A H -0.1251 0.7842 0.0238 0.059 Uiso 1 1 calc R . .
H5B H -0.1260 0.8114 -0.0951 0.059 Uiso 1 1 calc R . .
N6 N 0.07953(5) 0.89183(13) -0.15821(10) 0.0507(3) Uani 1 1 d . . .
H6A H 0.0609 0.8990 -0.2248 0.061 Uiso 1 1 calc R . .
H6B H 0.1196 0.9028 -0.1431 0.061 Uiso 1 1 calc R . .
O1 O 0.21423(5) 0.92208(12) -0.08163(8) 0.0593(3) Uani 1 1 d . . .
O2 O 0.20097(4) 0.89786(11) 0.09096(8) 0.0587(3) Uani 1 1 d . . .
O1W O 0.21071(5) 0.85873(12) 0.70241(9) 0.0594(3) Uani 1 1 d D . .
O2W O 0.19328(5) 0.80367(14) 0.36365(10) 0.0660(3) Uani 1 1 d D . .
H1WA H 0.2118(10) 0.9393(16) 0.6779(14) 0.093(7) Uiso 1 1 d D . .
H1WB H 0.2196(10) 0.8668(17) 0.7742(12) 0.084(6) Uiso 1 1 d D . .
H2WA H 0.2103(11) 0.8805(14) 0.379(2) 0.108(9) Uiso 1 1 d D . .
H2WB H 0.2229(9) 0.7538(16) 0.3479(17) 0.086(6) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0360(7) 0.0527(8) 0.0453(8) -0.0046(6) 0.0081(6) -0.0009(5)
C2 0.0348(7) 0.0463(7) 0.0503(8) -0.0005(6) 0.0090(6) -0.0006(5)
C3 0.0410(8) 0.0770(10) 0.0524(9) 0.0053(7) 0.0121(6) -0.0004(7)
C4 0.0388(8) 0.0858(12) 0.0747(11) 0.0101(9) 0.0195(7) -0.0033(7)
C5 0.0326(7) 0.0838(12) 0.0789(12) 0.0001(9) 0.0032(7) -0.0039(7)
C6 0.0434(9) 0.1068(14) 0.0573(10) 0.0009(9) -0.0023(7) -0.0009(9)
C7 0.0397(8) 0.0794(10) 0.0512(8) 0.0034(7) 0.0082(6) -0.0025(7)
C8 0.0340(6) 0.0452(7) 0.0404(7) -0.0022(5) 0.0079(5) 0.0013(5)
C9 0.0339(7) 0.0505(7) 0.0403(7) -0.0033(5) 0.0071(5) 0.0008(5)
C10 0.0329(7) 0.0452(7) 0.0409(7) -0.0023(5) 0.0074(5) 0.0003(5)
N1 0.0280(6) 0.0574(7) 0.0412(6) -0.0041(5) 0.0066(5) -0.0024(4)
N2 0.0319(6) 0.0578(7) 0.0387(6) 0.0001(5) 0.0067(5) -0.0019(5)
N3 0.0318(6) 0.0567(7) 0.0386(6) -0.0004(5) 0.0071(4) 0.0011(5)
N4 0.0338(6) 0.0944(10) 0.0403(6) 0.0024(6) 0.0032(5) -0.0028(6)
N5 0.0300(6) 0.0768(8) 0.0418(6) 0.0054(5) 0.0058(5) -0.0044(5)
N6 0.0339(6) 0.0768(8) 0.0430(6) 0.0018(5) 0.0111(5) -0.0025(5)
O1 0.0408(6) 0.0911(8) 0.0459(6) -0.0061(5) 0.0060(5) -0.0013(5)
O2 0.0352(5) 0.0916(8) 0.0504(6) -0.0024(5) 0.0105(4) -0.0103(5)
O1W 0.0548(7) 0.0801(8) 0.0435(6) 0.0005(5) 0.0079(5) -0.0047(6)
O2W 0.0444(6) 0.0851(9) 0.0697(8) -0.0090(6) 0.0124(5) 0.0037(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2497(17) . ?
C1 O2 1.2545(17) . ?
C1 C2 1.5039(19) . ?
C2 C7 1.377(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N6 1.3137(18) . ?
C8 N3 1.3301(17) . ?
C8 N1 1.3610(17) . ?
C9 N4 1.3149(17) . ?
C9 N2 1.3245(17) . ?
C9 N1 1.3519(17) . ?
C10 N5 1.3211(17) . ?
C10 N2 1.3501(17) . ?
C10 N3 1.3512(17) . ?
N1 H1 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
O1W H1WA 0.879(14) . ?
O1W H1WB 0.880(14) . ?
O2W H2WA 0.874(15) . ?
O2W H2WB 0.860(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 123.27(12) . . ?
O1 C1 C2 119.10(12) . . ?
O2 C1 C2 117.57(12) . . ?
C7 C2 C3 119.06(13) . . ?
C7 C2 C1 120.22(13) . . ?
C3 C2 C1 120.71(13) . . ?
C2 C3 C4 120.09(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.47(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.74(14) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.27(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.34(15) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
N6 C8 N3 121.27(12) . . ?
N6 C8 N1 117.34(12) . . ?
N3 C8 N1 121.38(12) . . ?
N4 C9 N2 120.41(12) . . ?
N4 C9 N1 117.79(12) . . ?
N2 C9 N1 121.80(11) . . ?
N5 C10 N2 116.76(12) . . ?
N5 C10 N3 117.34(12) . . ?
N2 C10 N3 125.90(11) . . ?
C9 N1 C8 119.46(11) . . ?
C9 N1 H1 120.3 . . ?
C8 N1 H1 120.3 . . ?
C9 N2 C10 115.73(11) . . ?
C8 N3 C10 115.63(11) . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C10 N5 H5A 120.0 . . ?
C10 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
H1WA O1W H1WB 104.2(14) . . ?
H2WA O2W H2WB 106.2(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.061
