# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H6 N6 O5'
_chemical_formula_weight         182.12

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.1750(14)
_cell_length_b                   7.2020(14)
_cell_length_c                   7.8560(16)
_cell_angle_alpha                66.12(3)
_cell_angle_beta                 65.34(3)
_cell_angle_gamma                68.51(3)
_cell_volume                     327.69(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_T_max  0.9648
_exptl_absorpt_process_details   '(North, Phillips & Mathews,1968)'

_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  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            1313
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         25.39
_reflns_number_total             1210
_reflns_number_gt                1065
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius,1994)'
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_reduction        'XCAD4(Harms & Wocadlo, 1995)'
_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)+(0.1000P)²+0.1200P] 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         1210
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C C 0.6089(3) 0.2388(3) 0.5688(3) 0.0268(4) Uani 1 1 d . . .
O1 O 0.2776(2) 0.1992(3) 0.5211(2) 0.0431(5) Uani 1 1 d . . .
N1 N 0.2996(2) 0.1311(2) 0.6856(2) 0.0276(4) Uani 1 1 d . . .
O2 O 0.1753(2) 0.0357(2) 0.8290(2) 0.0374(4) Uani 1 1 d . . .
N2 N 0.4567(2) 0.1546(2) 0.7217(2) 0.0285(4) Uani 1 1 d . . .
N3 N 0.6339(3) 0.3073(3) 0.3788(2) 0.0371(5) Uani 1 1 d . . .
H3A H 0.5433 0.3011 0.3374 0.044 Uiso 1 1 calc R . .
H3B H 0.7408 0.3580 0.2966 0.044 Uiso 1 1 calc R . .
N4 N 0.7576(3) 0.2558(3) 0.6220(3) 0.0372(5) Uani 1 1 d . . .
H4A H 0.8623 0.3069 0.5344 0.045 Uiso 1 1 calc R . .
N5 N 0.7387(3) 0.1884(3) 0.8234(3) 0.0347(4) Uani 1 1 d . . .
H5A H 0.8468 0.2081 0.8364 0.052 Uiso 1 1 calc R . .
H5B H 0.7389 0.0532 0.8734 0.052 Uiso 1 1 calc R . .
H5C H 0.6183 0.2615 0.8870 0.052 Uiso 1 1 calc R . .
O3 O 1.0950(3) 0.2396(3) 0.1694(3) 0.0563(5) Uani 1 1 d . . .
O4 O 1.3449(3) 0.3947(3) 0.0781(3) 0.0584(5) Uani 1 1 d . . .
O5 O 1.0335(2) 0.5047(2) 0.2614(3) 0.0455(5) Uani 1 1 d . . .
N6 N 1.1597(3) 0.3788(3) 0.1673(2) 0.0323(4) Uani 1 1 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
C 0.0241(9) 0.0230(9) 0.0264(10) -0.0071(7) -0.0023(7) -0.0050(7)
O1 0.0454(9) 0.0553(10) 0.0317(9) -0.0050(7) -0.0163(7) -0.0193(8)
N1 0.0264(8) 0.0288(8) 0.0258(8) -0.0074(6) -0.0068(6) -0.0072(6)
O2 0.0285(7) 0.0460(9) 0.0339(8) -0.0059(7) -0.0029(6) -0.0196(7)
N2 0.0241(8) 0.0349(9) 0.0246(8) -0.0073(7) -0.0045(6) -0.0105(7)
N3 0.0341(9) 0.0398(10) 0.0280(9) -0.0051(8) -0.0011(7) -0.0146(8)
N4 0.0299(9) 0.0471(10) 0.0298(9) -0.0031(8) -0.0033(7) -0.0207(8)
N5 0.0265(8) 0.0403(10) 0.0375(10) -0.0100(8) -0.0083(7) -0.0121(7)
O3 0.0459(10) 0.0556(11) 0.0760(13) -0.0376(10) -0.0007(9) -0.0227(8)
O4 0.0357(9) 0.0765(13) 0.0585(12) -0.0304(10) 0.0136(8) -0.0300(8)
O5 0.0336(8) 0.0374(8) 0.0614(11) -0.0221(8) -0.0066(7) -0.0055(6)
N6 0.0277(8) 0.0351(9) 0.0297(9) -0.0063(7) -0.0041(7) -0.0124(7)

_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
C N3 1.322(3) . ?
C N2 1.343(3) . ?
C N4 1.356(3) . ?
O1 N1 1.239(2) . ?
N1 O2 1.233(2) . ?
N1 N2 1.351(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 N5 1.416(3) . ?
N4 H4A 0.8600 . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
O3 N6 1.242(2) . ?
O4 N6 1.241(2) . ?
O5 N6 1.253(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C N2 130.33(18) . . ?
N3 C N4 116.33(17) . . ?
N2 C N4 113.33(17) . . ?
O2 N1 O1 120.85(16) . . ?
O2 N1 N2 115.52(15) . . ?
O1 N1 N2 123.63(16) . . ?
C N2 N1 118.36(16) . . ?
C N3 H3A 120.0 . . ?
C N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C N4 N5 119.28(16) . . ?
C N4 H4A 120.4 . . ?
N5 N4 H4A 120.4 . . ?
N4 N5 H5A 109.5 . . ?
N4 N5 H5B 109.5 . . ?
H5A N5 H5B 109.5 . . ?
N4 N5 H5C 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
O4 N6 O3 122.15(19) . . ?
O4 N6 O5 119.38(18) . . ?
O3 N6 O5 118.46(17) . . ?

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
N3 C N2 N1 0.3(3) . . . . ?
N4 C N2 N1 179.74(15) . . . . ?
O2 N1 N2 C 173.55(16) . . . . ?
O1 N1 N2 C -6.5(3) . . . . ?
N3 C N4 N5 179.02(17) . . . . ?
N2 C N4 N5 -0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 989437'
