# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelxle
_database_code_depnum_ccdc_archive 'CCDC 1048351'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;

#==========================================================================
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O8, 2(C3 H5 N2)'
_chemical_formula_sum            'C14 H16 N4 O8'
_chemical_formula_weight         368.31
_chemical_compound_source        Synthesis

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
_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                   6.4203(11)
_cell_length_b                   18.901(3)
_cell_length_c                   6.5776(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.022(4)
_cell_angle_gamma                90.00
_cell_volume                     774.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    540
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      27.98

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8297
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.98
_reflns_number_total             1504
_reflns_number_gt                1280
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_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.Hydrogen atoms on the 
 carbon atoms were placed at fixed positions using the HFIX instruction. 
 H-atoms on carboxylic groups were found from the Difference Fourier map. 
 They were refined with isotropic displacement parameters set
 to 1.2  Ueq of the attached atom. 
;

_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)+(0.0527P)²+0.2925P] 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         1504
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.0834(2) 0.10430(6) 0.3884(2) 0.0407(4) Uani 1 1 d . . .
O3 O 0.5898(2) -0.06749(7) 0.1509(2) 0.0439(4) Uani 1 1 d . . .
O4 O 0.8610(2) 0.00590(8) 0.1889(2) 0.0457(4) Uani 1 1 d . . .
H4OH H 0.9461 0.0487 0.2761 0.055 Uiso 1 1 d R . .
O2 O 0.3984(2) 0.15518(7) 0.4051(3) 0.0524(4) Uani 1 1 d . . .
N1 N 0.2468(3) -0.16759(10) 0.1428(3) 0.0523(5) Uani 1 1 d . . .
H1N1 H 0.3596 -0.1405 0.1729 0.063 Uiso 1 1 d R . .
N2 N 0.0483(3) -0.26019(9) 0.1162(2) 0.0440(4) Uani 1 1 d . . .
H2N2 H 0.0037 -0.3038 0.1087 0.053 Uiso 1 1 d R . .
C4 C 0.2861(3) 0.10233(9) 0.3936(3) 0.0343(4) Uani 1 1 d . . .
C7 C 0.6887(3) -0.01676(9) 0.2411(3) 0.0338(4) Uani 1 1 d . . .
C6 C 0.6215(3) 0.02023(9) 0.4194(3) 0.0315(4) Uani 1 1 d . . .
H6A H 0.6983 0.0649 0.4588 0.038 Uiso 1 1 calc R . .
C5 C 0.3765(3) 0.02837(9) 0.3856(3) 0.0313(4) Uani 1 1 d . . .
H5A H 0.3021 0.0045 0.2562 0.038 Uiso 1 1 calc R . .
C1 C 0.2488(3) -0.23770(11) 0.1424(3) 0.0459(5) Uani 1 1 d . . .
H1B H 0.3697 -0.2662 0.1578 0.055 Uiso 1 1 calc R . .
C3 C -0.0827(4) -0.20338(11) 0.1003(3) 0.0476(5) Uani 1 1 d . . .
H3A H -0.2311 -0.2045 0.0809 0.057 Uiso 1 1 calc R . .
C2 C 0.0386(3) -0.14566(10) 0.1176(3) 0.0449(5) Uani 1 1 d . . .
H2A H -0.0089 -0.0991 0.1133 0.054 Uiso 1 1 calc R . .

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
O1 0.0294(7) 0.0304(7) 0.0659(9) 0.0028(6) 0.0184(6) 0.0057(5)
O3 0.0394(8) 0.0380(8) 0.0578(9) -0.0108(6) 0.0187(6) -0.0050(6)
O4 0.0394(8) 0.0473(8) 0.0595(9) -0.0093(6) 0.0295(7) -0.0096(6)
O2 0.0397(8) 0.0298(8) 0.0896(11) 0.0030(7) 0.0189(7) -0.0033(6)
N1 0.0537(11) 0.0428(10) 0.0627(11) -0.0099(8) 0.0185(9) -0.0148(9)
N2 0.0588(11) 0.0290(9) 0.0462(10) -0.0026(6) 0.0169(8) -0.0089(7)
C4 0.0316(10) 0.0283(9) 0.0451(10) 0.0029(7) 0.0134(8) 0.0033(7)
C7 0.0303(9) 0.0301(10) 0.0447(10) 0.0023(7) 0.0164(8) 0.0025(7)
C6 0.0271(9) 0.0246(9) 0.0462(10) 0.0010(7) 0.0153(7) 0.0002(6)
C5 0.0260(9) 0.0268(9) 0.0436(10) 0.0001(7) 0.0132(7) 0.0009(7)
C1 0.0474(12) 0.0381(11) 0.0544(12) -0.0037(8) 0.0169(10) 0.0016(9)
C3 0.0411(11) 0.0514(13) 0.0513(12) 0.0017(9) 0.0130(9) 0.0030(9)
C2 0.0569(13) 0.0270(10) 0.0526(12) -0.0017(8) 0.0164(10) 0.0046(9)

_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 C4 1.294(2) . ?
O3 C7 1.222(2) . ?
O4 C7 1.308(2) . ?
O4 H4OH 1.0632 . ?
O2 C4 1.223(2) . ?
N1 C1 1.325(3) . ?
N1 C2 1.370(3) . ?
N1 H1N1 0.8700 . ?
N2 C1 1.326(3) . ?
N2 C3 1.353(3) . ?
N2 H2N2 0.8700 . ?
C4 C5 1.519(2) . ?
C7 C6 1.515(2) . ?
C6 C5 1.542(2) . ?
C6 C5 1.575(2) 3_656 ?
C6 H6A 0.9800 . ?
C5 C6 1.575(2) 3_656 ?
C5 H5A 0.9800 . ?
C1 H1B 0.9300 . ?
C3 C2 1.329(3) . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?

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
C7 O4 H4OH 117.7 . . ?
C1 N1 C2 108.17(17) . . ?
C1 N1 H1N1 125.6 . . ?
C2 N1 H1N1 125.7 . . ?
C1 N2 C3 108.75(17) . . ?
C1 N2 H2N2 127.4 . . ?
C3 N2 H2N2 123.9 . . ?
O2 C4 O1 123.49(16) . . ?
O2 C4 C5 121.95(16) . . ?
O1 C4 C5 114.57(15) . . ?
O3 C7 O4 120.20(17) . . ?
O3 C7 C6 121.73(16) . . ?
O4 C7 C6 118.04(16) . . ?
C7 C6 C5 113.98(14) . . ?
C7 C6 C5 114.42(14) . 3_656 ?
C5 C6 C5 88.99(13) . 3_656 ?
C7 C6 H6A 112.5 . . ?
C5 C6 H6A 112.5 . . ?
C5 C6 H6A 112.5 3_656 . ?
C4 C5 C6 118.15(14) . . ?
C4 C5 C6 115.87(14) . 3_656 ?
C6 C5 C6 91.01(13) . 3_656 ?
C4 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 3_656 . ?
N1 C1 N2 108.13(19) . . ?
N1 C1 H1B 125.9 . . ?
N2 C1 H1B 125.9 . . ?
C2 C3 N2 107.70(19) . . ?
C2 C3 H3A 126.1 . . ?
N2 C3 H3A 126.1 . . ?
C3 C2 N1 107.25(18) . . ?
C3 C2 H2A 126.4 . . ?
N1 C2 H2A 126.4 . . ?

_diffrn_measured_fraction_theta_max 0.800
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_shelxle
_database_code_depnum_ccdc_archive 'CCDC 1048352'
_audit_update_record             
;
2015-04-04 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;

#==========================================================================
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N2 O4'
_chemical_formula_sum            'C7 H8 N2 O4'
_chemical_formula_weight         184.15
_chemical_compound_source        Synthesis

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
_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                   7.646(5)
_cell_length_b                   7.480(5)
_cell_length_c                   13.756(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.521(19)
_cell_angle_gamma                90.00
_cell_volume                     781.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    742
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      28.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   'Multi Scan'
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku AFC7S Mercury'
_diffrn_measurement_method       'ω '
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Mercury (2x2 bin mode)'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9613
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.80
_reflns_number_total             1650
_reflns_number_gt                1137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_structure_refinement  'SHELXLTL-NT V5.1 (Bruker AXS, 1998)'
_computing_molecular_graphics    
;
SHELXLTL-NT V5.1 (Bruker AXS, 1998) and DIAMOND 
(Brandenburg, 1998)
;
_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. Hydrogen atoms on the 
 carbon atoms were placed at fixed positions using the HFIX instruction. 
 H-atoms on carboxylic groups were found from the Difference Fourier map. 
 They were refined with isotropic displacement parameters set
 to 1.2  Ueq of the attached atom. 
;

_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)+(0.1032P)²+0.0046P] 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         1650
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.2158
_refine_ls_wR_factor_gt          0.1967
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
O1 O 0.5008(3) 0.6368(3) 0.63747(18) 0.0463(7) Uani 1 1 d . . .
N1 N 0.2722(3) 0.2215(3) 0.57880(19) 0.0328(6) Uani 1 1 d . . .
C1 C 0.3449(4) 0.0811(5) 0.6277(3) 0.0439(9) Uani 1 1 d . . .
H1 H 0.4006 0.0836 0.6914 0.053 Uiso 1 1 calc R . .
C2 C 0.2372(5) -0.0134(5) 0.4827(3) 0.0488(9) Uani 1 1 d . . .
H2 H 0.2060 -0.0885 0.4297 0.059 Uiso 1 1 calc R . .
C3 C 0.2044(4) 0.1649(5) 0.4873(2) 0.0419(8) Uani 1 1 d . . .
H3 H 0.1470 0.2352 0.4378 0.050 Uiso 1 1 calc R . .
C4 C 0.4784(4) 0.4749(4) 0.6209(2) 0.0331(7) Uani 1 1 d . . .
C5 C 0.2868(4) 0.4078(4) 0.6115(2) 0.0316(7) Uani 1 1 d . . .
H5 H 0.2181 0.4814 0.5620 0.038 Uiso 1 1 calc R . .
C6 C 0.2113(4) 0.4354(5) 0.7088(2) 0.0406(8) Uani 1 1 d . . .
H6B H 0.2741 0.3578 0.7574 0.049 Uiso 1 1 calc R . .
H6A H 0.2343 0.5578 0.7299 0.049 Uiso 1 1 calc R . .
C7 C 0.0167(4) 0.4001(5) 0.7073(2) 0.0387(8) Uani 1 1 d . . .
O2 O 0.5964(3) 0.3606(3) 0.6155(2) 0.0582(8) Uani 1 1 d . . .
N2 N 0.3253(3) -0.0612(4) 0.5717(2) 0.0470(8) Uani 1 1 d . . .
H2N H 0.3616 -0.1756 0.5898 0.056 Uiso 1 1 d R . .
O3 O -0.0765(3) 0.4313(3) 0.62315(18) 0.0487(7) Uani 1 1 d . . .
H30H H -0.2067 0.4226 0.6401 0.058 Uiso 1 1 d R . .
O4 O -0.0469(4) 0.3536(5) 0.7790(2) 0.0797(11) 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
O1 0.0383(13) 0.0333(15) 0.0661(18) -0.0002(11) 0.0004(10) -0.0038(9)
N1 0.0289(12) 0.0294(15) 0.0402(16) -0.0016(11) 0.0035(9) -0.0001(9)
C1 0.0375(17) 0.042(2) 0.051(2) 0.0054(17) -0.0002(14) 0.0008(13)
C2 0.058(2) 0.039(2) 0.051(2) -0.0089(17) 0.0102(16) -0.0052(14)
C3 0.0458(18) 0.043(2) 0.0365(19) -0.0043(15) 0.0011(13) -0.0013(13)
C4 0.0307(15) 0.0327(19) 0.0357(18) -0.0015(13) 0.0027(11) 0.0000(11)
C5 0.0304(15) 0.0300(18) 0.0340(17) 0.0005(12) 0.0015(11) 0.0029(10)
C6 0.0352(17) 0.047(2) 0.040(2) -0.0070(15) 0.0055(13) 0.0004(13)
C7 0.0336(16) 0.042(2) 0.042(2) -0.0004(15) 0.0075(13) -0.0003(12)
O2 0.0276(12) 0.0419(16) 0.104(2) -0.0136(14) 0.0050(11) 0.0016(9)
N2 0.0433(16) 0.0307(17) 0.068(2) 0.0014(14) 0.0081(13) -0.0019(11)
O3 0.0312(12) 0.0660(18) 0.0494(16) 0.0046(12) 0.0065(10) -0.0034(10)
O4 0.0500(17) 0.132(3) 0.0589(19) 0.0272(19) 0.0117(13) -0.0088(16)

_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 C4 1.240(4) . ?
N1 C1 1.334(4) . ?
N1 C3 1.373(4) . ?
N1 C5 1.465(4) . ?
C1 N2 1.313(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(5) . ?
C2 N2 1.376(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 O2 1.251(4) . ?
C4 C5 1.540(4) . ?
C5 C6 1.531(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.509(5) . ?
C6 H6B 0.9700 . ?
C6 H6A 0.9700 . ?
C7 O4 1.200(4) . ?
C7 O3 1.310(4) . ?
N2 H2N 0.9244 . ?
O3 H30H 1.0499 . ?

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 N1 C3 108.2(3) . . ?
C1 N1 C5 125.5(3) . . ?
C3 N1 C5 125.6(3) . . ?
N2 C1 N1 109.2(3) . . ?
N2 C1 H1 125.4 . . ?
N1 C1 H1 125.4 . . ?
C3 C2 N2 106.8(3) . . ?
C3 C2 H2 126.6 . . ?
N2 C2 H2 126.6 . . ?
C2 C3 N1 107.0(3) . . ?
C2 C3 H3 126.5 . . ?
N1 C3 H3 126.5 . . ?
O1 C4 O2 126.3(3) . . ?
O1 C4 C5 116.3(2) . . ?
O2 C4 C5 117.3(3) . . ?
N1 C5 C6 111.9(3) . . ?
N1 C5 C4 112.0(2) . . ?
C6 C5 C4 109.4(2) . . ?
N1 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C4 C5 H5 107.8 . . ?
C7 C6 C5 115.7(3) . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
H6B C6 H6A 107.4 . . ?
O4 C7 O3 123.2(3) . . ?
O4 C7 C6 122.0(3) . . ?
O3 C7 C6 114.7(3) . . ?
C1 N2 C2 108.9(3) . . ?
C1 N2 H2N 125.5 . . ?
C2 N2 H2N 125.6 . . ?
C7 O3 H30H 103.1 . . ?

_diffrn_measured_fraction_theta_max 0.806
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.081
