# 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_L
_database_code_depnum_ccdc_archive 'CCDC 1012073'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N5 O7'
_chemical_formula_weight         347.25

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   12.745(5)
_cell_length_b                   8.223(5)
_cell_length_c                   13.910(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 112.259(5)
_cell_angle_gamma                90.000
_cell_volume                     1349.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3164
_cell_measurement_theta_min      3.4305
_cell_measurement_theta_max      74.1464

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8759
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         26.02
_reflns_number_total             2611
_reflns_number_gt                2409
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0607P)²+0.3980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2611
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.05165(8) 0.68629(12) 0.61816(7) 0.0290(2) Uani 1 1 d . . .
O2 O -0.34544(9) 1.15958(15) 0.38191(9) 0.0453(3) Uani 1 1 d . . .
O3 O -0.29824(9) 1.08494(14) 0.25534(8) 0.0402(3) Uani 1 1 d . . .
O4 O 0.38709(10) 0.37057(14) 0.27151(8) 0.0443(3) Uani 1 1 d . . .
O5 O 0.28707(8) 0.58000(13) 0.27608(8) 0.0364(3) Uani 1 1 d . . .
O6 O 0.54745(10) 0.09181(15) 0.71162(8) 0.0476(3) Uani 1 1 d . . .
O7 O 0.60025(10) 0.08799(17) 0.58191(9) 0.0539(4) Uani 1 1 d . . .
N1 N -0.28738(9) 1.07851(14) 0.34652(9) 0.0287(3) Uani 1 1 d . . .
N2 N 0.12225(8) 0.63644(13) 0.46288(8) 0.0240(2) Uani 1 1 d . . .
N3 N 0.19295(9) 0.58139(14) 0.41634(8) 0.0256(2) Uani 1 1 d . . .
H3 H 0.1815 0.6120 0.3525 0.031 Uiso 1 1 calc R . .
N4 N 0.34016(9) 0.45544(14) 0.31560(9) 0.0290(3) Uani 1 1 d . . .
N5 N 0.53937(10) 0.13748(15) 0.62548(9) 0.0329(3) Uani 1 1 d . . .
C1 C -0.03144(10) 0.77533(15) 0.54928(9) 0.0233(3) Uani 1 1 d . . .
C2 C -0.10782(10) 0.85403(16) 0.58442(10) 0.0257(3) Uani 1 1 d . . .
H2 H -0.1017 0.8386 0.6540 0.031 Uiso 1 1 calc R . .
C3 C -0.19154(10) 0.95334(16) 0.51925(10) 0.0261(3) Uani 1 1 d . . .
H3A H -0.2422 1.0083 0.5436 0.031 Uiso 1 1 calc R . .
C4 C -0.20054(10) 0.97168(15) 0.41676(10) 0.0245(3) Uani 1 1 d . . .
C5 C -0.12812(10) 0.89225(15) 0.37922(9) 0.0236(3) Uani 1 1 d . . .
H5 H -0.1370 0.9053 0.3087 0.028 Uiso 1 1 calc R . .
C6 C -0.04221(10) 0.79317(15) 0.44493(9) 0.0224(3) Uani 1 1 d . . .
C7 C 0.03553(10) 0.71833(15) 0.40376(9) 0.0235(3) Uani 1 1 d . . .
H7 H 0.0222 0.7300 0.3321 0.028 Uiso 1 1 calc R . .
C8 C 0.28019(10) 0.48034(15) 0.46753(9) 0.0236(3) Uani 1 1 d . . .
C9 C 0.30330(10) 0.43418(16) 0.57180(10) 0.0256(3) Uani 1 1 d . . .
H9 H 0.2597 0.4805 0.6071 0.031 Uiso 1 1 calc R . .
C10 C 0.38673(11) 0.32474(16) 0.62303(10) 0.0268(3) Uani 1 1 d . . .
H10 H 0.4002 0.2952 0.6927 0.032 Uiso 1 1 calc R . .
C11 C 0.45209(10) 0.25669(16) 0.57186(10) 0.0270(3) Uani 1 1 d . . .
C12 C 0.43497(11) 0.29884(16) 0.47134(10) 0.0275(3) Uani 1 1 d . . .
H12 H 0.4800 0.2521 0.4375 0.033 Uiso 1 1 calc R . .
C13 C 0.35089(11) 0.41082(16) 0.42014(10) 0.0252(3) Uani 1 1 d . . .
H101 H 0.0950(17) 0.647(3) 0.5850(16) 0.058(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3442(16) . ?
O1 H101 0.90(2) . ?
O2 N1 1.2290(15) . ?
O3 N1 1.2236(15) . ?
O4 N4 1.2243(15) . ?
O5 N4 1.2358(16) . ?
O6 N5 1.2223(17) . ?
O7 N5 1.2211(16) . ?
N1 C4 1.4601(16) . ?
N2 C7 1.2894(17) . ?
N2 N3 1.3704(15) . ?
N3 C8 1.3542(17) . ?
N3 H3 0.8800 . ?
N4 C13 1.4550(17) . ?
N5 C11 1.4581(17) . ?
C1 C2 1.4021(18) . ?
C1 C6 1.4129(17) . ?
C2 C3 1.3763(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3944(18) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3842(18) . ?
C5 C6 1.3928(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4555(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.4180(18) . ?
C8 C13 1.4223(17) . ?
C9 C10 1.3690(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4011(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3753(19) . ?
C12 C13 1.3876(19) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H101 107.5(13) . . ?
O3 N1 O2 122.88(11) . . ?
O3 N1 C4 118.62(11) . . ?
O2 N1 C4 118.50(11) . . ?
C7 N2 N3 115.42(10) . . ?
C8 N3 N2 120.67(10) . . ?
C8 N3 H3 119.7 . . ?
N2 N3 H3 119.7 . . ?
O4 N4 O5 122.59(11) . . ?
O4 N4 C13 118.56(12) . . ?
O5 N4 C13 118.81(10) . . ?
O7 N5 O6 123.42(12) . . ?
O7 N5 C11 118.37(12) . . ?
O6 N5 C11 118.21(11) . . ?
O1 C1 C2 117.81(11) . . ?
O1 C1 C6 122.18(11) . . ?
C2 C1 C6 120.01(11) . . ?
C3 C2 C1 120.78(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 118.72(11) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C5 C4 C3 121.75(12) . . ?
C5 C4 N1 118.44(11) . . ?
C3 C4 N1 119.81(11) . . ?
C4 C5 C6 119.95(11) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 118.76(11) . . ?
C5 C6 C7 118.18(11) . . ?
C1 C6 C7 123.00(11) . . ?
N2 C7 C6 121.11(11) . . ?
N2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
N3 C8 C9 120.87(11) . . ?
N3 C8 C13 122.75(11) . . ?
C9 C8 C13 116.35(11) . . ?
C10 C9 C8 121.85(11) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 119.48(12) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.33(12) . . ?
C12 C11 N5 119.08(11) . . ?
C10 C11 N5 119.59(12) . . ?
C11 C12 C13 118.90(11) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 122.04(11) . . ?
C12 C13 N4 116.24(11) . . ?
C8 C13 N4 121.71(11) . . ?

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
C7 N2 N3 C8 -173.26(11) . . . . ?
O1 C1 C2 C3 176.88(11) . . . . ?
C6 C1 C2 C3 -2.12(18) . . . . ?
C1 C2 C3 C4 1.31(19) . . . . ?
C2 C3 C4 C5 0.34(19) . . . . ?
C2 C3 C4 N1 -178.96(11) . . . . ?
O3 N1 C4 C5 5.15(17) . . . . ?
O2 N1 C4 C5 -173.97(12) . . . . ?
O3 N1 C4 C3 -175.54(12) . . . . ?
O2 N1 C4 C3 5.34(18) . . . . ?
C3 C4 C5 C6 -1.17(18) . . . . ?
N1 C4 C5 C6 178.13(10) . . . . ?
C4 C5 C6 C1 0.36(17) . . . . ?
C4 C5 C6 C7 -177.00(11) . . . . ?
O1 C1 C6 C5 -177.69(11) . . . . ?
C2 C1 C6 C5 1.25(18) . . . . ?
O1 C1 C6 C7 -0.47(18) . . . . ?
C2 C1 C6 C7 178.48(11) . . . . ?
N3 N2 C7 C6 -175.82(10) . . . . ?
C5 C6 C7 N2 174.21(11) . . . . ?
C1 C6 C7 N2 -3.03(18) . . . . ?
N2 N3 C8 C9 -2.52(18) . . . . ?
N2 N3 C8 C13 175.41(11) . . . . ?
N3 C8 C9 C10 176.06(12) . . . . ?
C13 C8 C9 C10 -2.00(18) . . . . ?
C8 C9 C10 C11 0.47(19) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C9 C10 C11 N5 -178.68(11) . . . . ?
O7 N5 C11 C12 5.4(2) . . . . ?
O6 N5 C11 C12 -174.30(13) . . . . ?
O7 N5 C11 C10 -175.20(13) . . . . ?
O6 N5 C11 C10 5.1(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
N5 C11 C12 C13 179.20(11) . . . . ?
C11 C12 C13 C8 -1.51(19) . . . . ?
C11 C12 C13 N4 177.51(11) . . . . ?
N3 C8 C13 C12 -175.49(12) . . . . ?
C9 C8 C13 C12 2.53(18) . . . . ?
N3 C8 C13 N4 5.55(19) . . . . ?
C9 C8 C13 N4 -176.43(11) . . . . ?
O4 N4 C13 C12 14.84(17) . . . . ?
O5 N4 C13 C12 -162.98(12) . . . . ?
O4 N4 C13 C8 -166.14(12) . . . . ?
O5 N4 C13 C8 16.04(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
