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

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#
#                 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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_C10H12N2O5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N2 O5'
_chemical_formula_sum            'C10 H12 N2 O5'
_chemical_formula_weight         240.22

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   P2(1)

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

_cell_length_a                   4.89000(10)
_cell_length_b                   13.3653(4)
_cell_length_c                   15.1691(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.897(2)
_cell_angle_gamma                90.00
_cell_volume                     990.13(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      28.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    none
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22680
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         28.39
_reflns_number_total             4953
_reflns_number_gt                4632
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0421P)²+0.1666P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       na
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4953
_refine_ls_number_parameters     325
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_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 1.0943(2) 0.16704(8) 0.29893(6) 0.0164(2) Uani 1 1 d . . .
O2 O 1.3727(2) -0.14672(8) 0.23374(7) 0.0177(2) Uani 1 1 d . . .
O3 O 0.44634(18) 0.14345(8) 0.12762(6) 0.01346(19) Uani 1 1 d . . .
O4 O 0.5759(2) -0.03398(8) -0.10729(7) 0.0203(2) Uani 1 1 d D . .
H4O H 0.532(4) 0.0232(13) -0.1273(14) 0.030 Uiso 1 1 d D . .
O5 O 0.5780(2) 0.27899(8) -0.03407(7) 0.0190(2) Uani 1 1 d D . .
H5O H 0.532(4) 0.2564(15) -0.0813(11) 0.028 Uiso 1 1 d D . .
N1 N 1.2185(2) 0.00681(9) 0.26926(8) 0.0130(2) Uani 1 1 d D . .
H1N H 1.344(3) 0.0109(14) 0.3119(10) 0.016 Uiso 1 1 d D . .
N2 N 0.8709(2) 0.08585(9) 0.18531(7) 0.0112(2) Uani 1 1 d . . .
C1 C 1.0649(3) 0.09122(11) 0.25411(8) 0.0127(3) Uani 1 1 d . . .
C2 C 1.2141(3) -0.07684(11) 0.21631(9) 0.0129(3) Uani 1 1 d . . .
C3 C 1.0197(3) -0.07456(11) 0.14255(9) 0.0131(3) Uani 1 1 d . . .
H3 H 1.0053 -0.1303 0.1038 0.016 Uiso 1 1 calc R . .
C4 C 0.8564(3) 0.00584(10) 0.12735(8) 0.0109(2) Uani 1 1 d . . .
C5 C 0.6527(3) 0.01208(10) 0.04832(9) 0.0112(2) Uani 1 1 d . . .
H5 H 0.4993 -0.0343 0.0612 0.013 Uiso 1 1 calc R . .
C6 C 0.5266(3) 0.11678(10) 0.03975(9) 0.0120(3) Uani 1 1 d . . .
H6 H 0.3619 0.1152 -0.0021 0.014 Uiso 1 1 calc R . .
C7 C 0.7196(3) 0.20258(10) 0.01463(9) 0.0133(3) Uani 1 1 d . . .
H7 H 0.8771 0.1765 -0.0181 0.016 Uiso 1 1 calc R . .
C8 C 0.8179(3) 0.24672(10) 0.10453(9) 0.0136(3) Uani 1 1 d . . .
H8A H 1.0203 0.2469 0.1116 0.016 Uiso 1 1 calc R . .
H8B H 0.7493 0.3158 0.1117 0.016 Uiso 1 1 calc R . .
C9 C 0.6936(3) 0.17574(10) 0.16962(9) 0.0125(3) Uani 1 1 d . . .
H9 H 0.6598 0.2106 0.2264 0.015 Uiso 1 1 calc R . .
C10 C 0.7747(3) -0.02709(11) -0.03625(9) 0.0153(3) Uani 1 1 d . . .
H10A H 0.9234 0.0182 -0.0531 0.018 Uiso 1 1 calc R . .
H10B H 0.8554 -0.0940 -0.0247 0.018 Uiso 1 1 calc R . .
O6 O 1.0119(2) 0.32249(8) 0.60274(6) 0.0156(2) Uani 1 1 d . . .
O7 O 1.3787(2) 0.14811(9) 0.83574(7) 0.0218(2) Uani 1 1 d . . .
O8 O 0.42057(19) 0.11535(7) 0.55851(7) 0.0135(2) Uani 1 1 d . . .
O9 O 0.6304(2) -0.17964(8) 0.61522(8) 0.0241(2) Uani 1 1 d D . .
H9O H 0.692(4) -0.2359(13) 0.6328(14) 0.036 Uiso 1 1 d D . .
O10 O 0.6604(2) -0.01054(8) 0.39590(7) 0.0182(2) Uani 1 1 d D . .
H10O H 0.743(4) -0.0647(13) 0.3914(14) 0.027 Uiso 1 1 d D . .
N3 N 1.1845(2) 0.23529(9) 0.72149(8) 0.0122(2) Uani 1 1 d D . .
H3N H 1.302(3) 0.2816(12) 0.7324(12) 0.015 Uiso 1 1 d D . .
N4 N 0.8300(2) 0.16958(9) 0.63113(7) 0.0111(2) Uani 1 1 d . . .
C11 C 1.0097(3) 0.24754(10) 0.64921(9) 0.0119(3) Uani 1 1 d . . .
C12 C 1.2073(3) 0.15063(11) 0.77293(9) 0.0140(3) Uani 1 1 d . . .
C13 C 1.0303(3) 0.06995(11) 0.74651(9) 0.0140(3) Uani 1 1 d . . .
H13 H 1.0383 0.0090 0.7787 0.017 Uiso 1 1 calc R . .
C14 C 0.8513(3) 0.07950(11) 0.67608(9) 0.0118(2) Uani 1 1 d . . .
C15 C 0.6698(3) -0.00538(10) 0.64299(9) 0.0131(3) Uani 1 1 d . . .
H15 H 0.5137 -0.0091 0.6830 0.016 Uiso 1 1 calc R . .
C16 C 0.5470(3) 0.01769(11) 0.55069(9) 0.0132(3) Uani 1 1 d . . .
H16 H 0.4066 -0.0336 0.5323 0.016 Uiso 1 1 calc R . .
C17 C 0.7571(3) 0.03086(11) 0.47841(9) 0.0137(3) Uani 1 1 d . . .
H17 H 0.9368 0.0003 0.4979 0.016 Uiso 1 1 calc R . .
C18 C 0.7851(3) 0.14478(11) 0.47053(9) 0.0139(3) Uani 1 1 d . . .
H18A H 0.9797 0.1655 0.4728 0.017 Uiso 1 1 calc R . .
H18B H 0.6930 0.1699 0.4153 0.017 Uiso 1 1 calc R . .
C19 C 0.6421(3) 0.18128(11) 0.55099(9) 0.0121(3) Uani 1 1 d . . .
H19 H 0.5786 0.2520 0.5435 0.015 Uiso 1 1 calc R . .
C20 C 0.8165(3) -0.10597(11) 0.64934(10) 0.0173(3) Uani 1 1 d . . .
H20A H 0.9825 -0.1046 0.6146 0.021 Uiso 1 1 calc R . .
H20B H 0.8722 -0.1211 0.7116 0.021 Uiso 1 1 calc R . .


_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 1.2248(17) . ?
O2 C2 1.2340(17) . ?
O3 C9 1.4059(16) . ?
O3 C6 1.4527(16) . ?
O4 C10 1.4174(17) . ?
O4 H4O 0.845(15) . ?
O5 C7 1.4199(17) . ?
O5 H5O 0.800(15) . ?
N1 C1 1.3684(18) . ?
N1 C2 1.3762(18) . ?
N1 H1N 0.871(14) . ?
N2 C1 1.3762(17) . ?
N2 C4 1.3839(17) . ?
N2 C9 1.4936(17) . ?
C2 C3 1.4313(18) . ?
C3 C4 1.3515(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.5218(17) . ?
C5 C6 1.5323(19) . ?
C5 C10 1.5338(18) . ?
C5 H5 1.0000 . ?
C6 C7 1.5450(18) . ?
C6 H6 1.0000 . ?
C7 C8 1.5403(19) . ?
C7 H7 1.0000 . ?
C8 C9 1.5182(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O6 C11 1.2253(17) . ?
O7 C12 1.2374(17) . ?
O8 C19 1.4055(16) . ?
O8 C16 1.4517(16) . ?
O9 C20 1.4208(18) . ?
O9 H9O 0.849(15) . ?
O10 C17 1.4271(16) . ?
O10 H10O 0.833(15) . ?
N3 C11 1.3656(17) . ?
N3 C12 1.3758(19) . ?
N3 H3N 0.856(14) . ?
N4 C11 1.3815(17) . ?
N4 C14 1.3849(17) . ?
N4 C19 1.4946(16) . ?
C12 C13 1.4273(19) . ?
C13 C14 1.3526(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.5105(19) . ?
C15 C20 1.525(2) . ?
C15 C16 1.5269(18) . ?
C15 H15 1.0000 . ?
C16 C17 1.5501(18) . ?
C16 H16 1.0000 . ?
C17 C18 1.534(2) . ?
C17 H17 1.0000 . ?
C18 C19 1.5174(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19 1.0000 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C9 O3 C6 103.01(9) . . ?
C10 O4 H4O 111.4(14) . . ?
C7 O5 H5O 107.6(15) . . ?
C1 N1 C2 125.41(12) . . ?
C1 N1 H1N 115.7(12) . . ?
C2 N1 H1N 118.3(12) . . ?
C1 N2 C4 122.21(12) . . ?
C1 N2 C9 116.82(11) . . ?
C4 N2 C9 120.65(11) . . ?
O1 C1 N1 122.73(12) . . ?
O1 C1 N2 121.42(13) . . ?
N1 C1 N2 115.85(12) . . ?
O2 C2 N1 119.91(13) . . ?
O2 C2 C3 124.67(13) . . ?
N1 C2 C3 115.42(12) . . ?
C4 C3 C2 120.90(13) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 N2 119.69(12) . . ?
C3 C4 C5 122.38(12) . . ?
N2 C4 C5 117.94(12) . . ?
C4 C5 C6 111.20(11) . . ?
C4 C5 C10 111.93(10) . . ?
C6 C5 C10 114.38(11) . . ?
C4 C5 H5 106.2 . . ?
C6 C5 H5 106.2 . . ?
C10 C5 H5 106.2 . . ?
O3 C6 C5 105.81(10) . . ?
O3 C6 C7 103.94(11) . . ?
C5 C6 C7 116.77(10) . . ?
O3 C6 H6 110.0 . . ?
C5 C6 H6 110.0 . . ?
C7 C6 H6 110.0 . . ?
O5 C7 C8 107.89(11) . . ?
O5 C7 C6 111.98(11) . . ?
C8 C7 C6 103.48(10) . . ?
O5 C7 H7 111.1 . . ?
C8 C7 H7 111.1 . . ?
C6 C7 H7 111.1 . . ?
C9 C8 C7 102.66(11) . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
O3 C9 N2 107.71(10) . . ?
O3 C9 C8 105.09(11) . . ?
N2 C9 C8 110.99(10) . . ?
O3 C9 H9 111.0 . . ?
N2 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
O4 C10 C5 112.17(11) . . ?
O4 C10 H10A 109.2 . . ?
C5 C10 H10A 109.2 . . ?
O4 C10 H10B 109.2 . . ?
C5 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C19 O8 C16 102.94(9) . . ?
C20 O9 H9O 106.8(15) . . ?
C17 O10 H10O 105.5(14) . . ?
C11 N3 C12 125.69(12) . . ?
C11 N3 H3N 117.2(12) . . ?
C12 N3 H3N 116.7(12) . . ?
C11 N4 C14 121.78(11) . . ?
C11 N4 C19 116.19(11) . . ?
C14 N4 C19 121.28(11) . . ?
O6 C11 N3 122.46(12) . . ?
O6 C11 N4 121.76(12) . . ?
N3 C11 N4 115.78(12) . . ?
O7 C12 N3 119.43(13) . . ?
O7 C12 C13 124.97(14) . . ?
N3 C12 C13 115.57(12) . . ?
C14 C13 C12 120.62(13) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 N4 120.03(12) . . ?
C13 C14 C15 122.51(13) . . ?
N4 C14 C15 117.46(11) . . ?
C14 C15 C20 112.00(11) . . ?
C14 C15 C16 110.51(11) . . ?
C20 C15 C16 113.46(12) . . ?
C14 C15 H15 106.8 . . ?
C20 C15 H15 106.8 . . ?
C16 C15 H15 106.8 . . ?
O8 C16 C15 104.83(11) . . ?
O8 C16 C17 104.83(11) . . ?
C15 C16 C17 115.29(10) . . ?
O8 C16 H16 110.5 . . ?
C15 C16 H16 110.5 . . ?
C17 C16 H16 110.5 . . ?
O10 C17 C18 110.09(11) . . ?
O10 C17 C16 111.96(11) . . ?
C18 C17 C16 103.46(11) . . ?
O10 C17 H17 110.4 . . ?
C18 C17 H17 110.4 . . ?
C16 C17 H17 110.4 . . ?
C19 C18 C17 102.12(11) . . ?
C19 C18 H18A 111.3 . . ?
C17 C18 H18A 111.3 . . ?
C19 C18 H18B 111.3 . . ?
C17 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
O8 C19 N4 108.25(11) . . ?
O8 C19 C18 104.60(11) . . ?
N4 C19 C18 109.34(10) . . ?
O8 C19 H19 111.5 . . ?
N4 C19 H19 111.5 . . ?
C18 C19 H19 111.5 . . ?
O9 C20 C15 107.29(11) . . ?
O9 C20 H20A 110.3 . . ?
C15 C20 H20A 110.3 . . ?
O9 C20 H20B 110.3 . . ?
C15 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?

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 N1 C1 O1 -173.25(12) . . . . ?
C2 N1 C1 N2 7.37(18) . . . . ?
C4 N2 C1 O1 171.95(12) . . . . ?
C9 N2 C1 O1 -1.60(17) . . . . ?
C4 N2 C1 N1 -8.66(17) . . . . ?
C9 N2 C1 N1 177.79(11) . . . . ?
C1 N1 C2 O2 176.00(12) . . . . ?
C1 N1 C2 C3 -3.45(18) . . . . ?
O2 C2 C3 C4 -178.85(13) . . . . ?
N1 C2 C3 C4 0.58(18) . . . . ?
C2 C3 C4 N2 -2.04(19) . . . . ?
C2 C3 C4 C5 178.37(11) . . . . ?
C1 N2 C4 C3 6.35(18) . . . . ?
C9 N2 C4 C3 179.66(12) . . . . ?
C1 N2 C4 C5 -174.05(11) . . . . ?
C9 N2 C4 C5 -0.74(16) . . . . ?
C3 C4 C5 C6 -171.54(12) . . . . ?
N2 C4 C5 C6 8.87(15) . . . . ?
C3 C4 C5 C10 -42.24(17) . . . . ?
N2 C4 C5 C10 138.17(12) . . . . ?
C9 O3 C6 C5 80.62(11) . . . . ?
C9 O3 C6 C7 -42.93(12) . . . . ?
C4 C5 C6 O3 -47.02(13) . . . . ?
C10 C5 C6 O3 -175.01(10) . . . . ?
C4 C5 C6 C7 68.02(14) . . . . ?
C10 C5 C6 C7 -59.97(15) . . . . ?
O3 C6 C7 O5 -94.05(12) . . . . ?
C5 C6 C7 O5 149.87(11) . . . . ?
O3 C6 C7 C8 21.89(13) . . . . ?
C5 C6 C7 C8 -94.19(13) . . . . ?
O5 C7 C8 C9 124.05(11) . . . . ?
C6 C7 C8 C9 5.24(13) . . . . ?
C6 O3 C9 N2 -71.07(12) . . . . ?
C6 O3 C9 C8 47.33(12) . . . . ?
C1 N2 C9 O3 -154.38(10) . . . . ?
C4 N2 C9 O3 31.96(15) . . . . ?
C1 N2 C9 C8 91.08(13) . . . . ?
C4 N2 C9 C8 -82.58(14) . . . . ?
C7 C8 C9 O3 -32.01(13) . . . . ?
C7 C8 C9 N2 84.15(12) . . . . ?
C4 C5 C10 O4 172.14(11) . . . . ?
C6 C5 C10 O4 -60.24(15) . . . . ?
C12 N3 C11 O6 -175.09(13) . . . . ?
C12 N3 C11 N4 4.52(18) . . . . ?
C14 N4 C11 O6 171.12(12) . . . . ?
C19 N4 C11 O6 0.93(17) . . . . ?
C14 N4 C11 N3 -8.49(17) . . . . ?
C19 N4 C11 N3 -178.68(11) . . . . ?
C11 N3 C12 O7 178.35(13) . . . . ?
C11 N3 C12 C13 0.14(19) . . . . ?
O7 C12 C13 C14 -179.20(13) . . . . ?
N3 C12 C13 C14 -1.10(19) . . . . ?
C12 C13 C14 N4 -2.79(19) . . . . ?
C12 C13 C14 C15 176.96(12) . . . . ?
C11 N4 C14 C13 7.90(18) . . . . ?
C19 N4 C14 C13 177.60(12) . . . . ?
C11 N4 C14 C15 -171.85(11) . . . . ?
C19 N4 C14 C15 -2.16(17) . . . . ?
C13 C14 C15 C20 -37.74(17) . . . . ?
N4 C14 C15 C20 142.00(12) . . . . ?
C13 C14 C15 C16 -165.32(12) . . . . ?
N4 C14 C15 C16 14.43(16) . . . . ?
C19 O8 C16 C15 82.35(11) . . . . ?
C19 O8 C16 C17 -39.48(12) . . . . ?
C14 C15 C16 O8 -52.84(13) . . . . ?
C20 C15 C16 O8 -179.60(10) . . . . ?
C14 C15 C16 C17 61.86(15) . . . . ?
C20 C15 C16 C17 -64.90(15) . . . . ?
O8 C16 C17 O10 -102.96(12) . . . . ?
C15 C16 C17 O10 142.33(12) . . . . ?
O8 C16 C17 C18 15.55(13) . . . . ?
C15 C16 C17 C18 -99.16(13) . . . . ?
O10 C17 C18 C19 131.81(11) . . . . ?
C16 C17 C18 C19 12.01(13) . . . . ?
C16 O8 C19 N4 -68.15(12) . . . . ?
C16 O8 C19 C18 48.35(12) . . . . ?
C11 N4 C19 O8 -160.55(11) . . . . ?
C14 N4 C19 O8 29.20(15) . . . . ?
C11 N4 C19 C18 86.05(14) . . . . ?
C14 N4 C19 C18 -84.19(14) . . . . ?
C17 C18 C19 O8 -37.20(13) . . . . ?
C17 C18 C19 N4 78.55(12) . . . . ?
C14 C15 C20 O9 -178.93(11) . . . . ?
C16 C15 C20 O9 -52.95(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4O O7 0.845(15) 1.904(16) 2.7412(16) 171(2) 1_454
O5 H5O O7 0.800(15) 2.035(17) 2.7775(15) 154(2) 1_454
N1 H1N O10 0.871(14) 1.975(14) 2.8272(16) 166.0(17) 1_655
O9 H9O O1 0.849(15) 1.933(16) 2.7441(15) 160(2) 2_746
O10 H10O O6 0.833(15) 1.926(16) 2.7468(15) 168(2) 2_746
N3 H3N O2 0.856(14) 1.904(14) 2.7365(15) 163.9(17) 2_856

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1003704'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_C10H12N2O5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N2 O5'
_chemical_formula_sum            'C10 H12 N2 O5'
_chemical_formula_weight         240.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.8546(6)
_cell_length_b                   5.0786(4)
_cell_length_c                   12.4411(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.701(5)
_cell_angle_gamma                90.00
_cell_volume                     484.14(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3587
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      66.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    none
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    1.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8469
_exptl_absorpt_correction_T_max  0.9344
_exptl_absorpt_process_details   
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4042
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         66.17
_reflns_number_total             1588
_reflns_number_gt                1544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0515P)²+0.0553P] 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       na
_chemical_absolute_configuration syn
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         1588
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.38147(16) 0.6865(3) 0.48718(10) 0.0219(3) Uani 1 1 d . . .
O2 O -0.01175(16) 0.0238(3) 0.39123(10) 0.0216(3) Uani 1 1 d . . .
O3 O 0.45671(15) 0.7287(3) 0.18133(10) 0.0159(3) Uani 1 1 d . . .
O4 O 0.18897(15) 0.4317(3) -0.05922(9) 0.0186(3) Uani 1 1 d . . .
H4O H 0.194(3) 0.289(6) -0.087(2) 0.028 Uiso 1 1 d . . .
O5 O 0.80225(15) 0.4305(3) 0.15229(10) 0.0185(3) Uani 1 1 d . . .
H5O H 0.824(3) 0.302(6) 0.1238(19) 0.028 Uiso 1 1 d . . .
N1 N 0.18010(18) 0.3628(3) 0.43539(12) 0.0172(4) Uani 1 1 d . . .
H1N H 0.137(3) 0.392(6) 0.4885(18) 0.021 Uiso 1 1 d . . .
N2 N 0.36052(18) 0.4927(3) 0.31921(11) 0.0152(3) Uani 1 1 d . . .
C1 C 0.3130(2) 0.5245(4) 0.41933(14) 0.0164(4) Uani 1 1 d . . .
C2 C 0.1047(2) 0.1591(4) 0.36795(14) 0.0163(4) Uani 1 1 d . . .
C3 C 0.1691(2) 0.1313(4) 0.26875(15) 0.0167(4) Uani 1 1 d . . .
H3 H 0.1276 -0.0088 0.2193 0.020 Uiso 1 1 calc R . .
C4 C 0.2869(2) 0.3009(4) 0.24505(14) 0.0147(4) Uani 1 1 d . . .
C5 C 0.3295(2) 0.3073(4) 0.13188(14) 0.0148(4) Uani 1 1 d . . .
H5 H 0.348(3) 0.129(5) 0.1118(17) 0.018 Uiso 1 1 d . . .
C6 C 0.4863(2) 0.4818(4) 0.13048(14) 0.0155(4) Uani 1 1 d . . .
H6 H 0.495(3) 0.519(5) 0.0566(17) 0.019 Uiso 1 1 d . . .
C7 C 0.6578(2) 0.3734(4) 0.20169(15) 0.0158(4) Uani 1 1 d . . .
H7 H 0.647(3) 0.186(6) 0.2132(17) 0.019 Uiso 1 1 d . . .
C8 C 0.6753(2) 0.5270(4) 0.30996(14) 0.0174(4) Uani 1 1 d . . .
H8A H 0.6951 0.4064 0.3741 0.021 Uiso 1 1 calc R . .
H8B H 0.7724 0.6552 0.3198 0.021 Uiso 1 1 calc R . .
C9 C 0.5002(2) 0.6664(4) 0.29548(14) 0.0163(4) Uani 1 1 d . . .
H9 H 0.498(3) 0.827(5) 0.3360(17) 0.020 Uiso 1 1 d . . .
C10 C 0.1663(2) 0.4120(4) 0.05043(14) 0.0171(4) Uani 1 1 d . . .
H10A H 0.0669 0.2931 0.0517 0.020 Uiso 1 1 calc R . .
H10B H 0.1367 0.5879 0.0753 0.020 Uiso 1 1 calc R . .


_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 1.217(2) . ?
O2 C2 1.229(2) . ?
O3 C9 1.421(2) . ?
O3 C6 1.446(2) . ?
O4 C10 1.4175(19) . ?
O4 H4O 0.81(3) . ?
O5 C7 1.434(2) . ?
O5 H5O 0.78(3) . ?
N1 C1 1.376(2) . ?
N1 C2 1.381(2) . ?
N1 H1N 0.82(2) . ?
N2 C4 1.379(2) . ?
N2 C1 1.386(2) . ?
N2 C9 1.487(2) . ?
C2 C3 1.440(2) . ?
C3 C4 1.343(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.518(2) . ?
C5 C6 1.520(3) . ?
C5 C10 1.543(2) . ?
C5 H5 0.96(3) . ?
C6 C7 1.542(2) . ?
C6 H6 0.95(2) . ?
C7 C8 1.536(2) . ?
C7 H7 0.97(3) . ?
C8 C9 1.522(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.96(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C9 O3 C6 102.56(14) . . ?
C10 O4 H4O 112.5(18) . . ?
C7 O5 H5O 107.3(19) . . ?
C1 N1 C2 126.60(15) . . ?
C1 N1 H1N 118.0(18) . . ?
C2 N1 H1N 115.3(18) . . ?
C4 N2 C1 121.81(15) . . ?
C4 N2 C9 120.38(14) . . ?
C1 N2 C9 117.76(14) . . ?
O1 C1 N1 122.46(16) . . ?
O1 C1 N2 122.46(16) . . ?
N1 C1 N2 115.07(16) . . ?
O2 C2 N1 121.19(16) . . ?
O2 C2 C3 124.56(17) . . ?
N1 C2 C3 114.19(16) . . ?
C4 C3 C2 120.93(17) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 N2 120.94(16) . . ?
C3 C4 C5 121.38(16) . . ?
N2 C4 C5 117.38(15) . . ?
C4 C5 C6 111.58(14) . . ?
C4 C5 C10 107.19(13) . . ?
C6 C5 C10 110.48(15) . . ?
C4 C5 H5 107.3(13) . . ?
C6 C5 H5 112.3(12) . . ?
C10 C5 H5 107.8(12) . . ?
O3 C6 C5 106.98(13) . . ?
O3 C6 C7 105.20(14) . . ?
C5 C6 C7 113.14(16) . . ?
O3 C6 H6 107.5(15) . . ?
C5 C6 H6 110.7(13) . . ?
C7 C6 H6 112.8(12) . . ?
O5 C7 C8 110.27(14) . . ?
O5 C7 C6 110.81(14) . . ?
C8 C7 C6 102.78(14) . . ?
O5 C7 H7 111.4(13) . . ?
C8 C7 H7 111.3(13) . . ?
C6 C7 H7 110.0(12) . . ?
C9 C8 C7 103.18(13) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
O3 C9 N2 107.76(13) . . ?
O3 C9 C8 103.53(13) . . ?
N2 C9 C8 112.80(16) . . ?
O3 C9 H9 107.8(13) . . ?
N2 C9 H9 107.6(13) . . ?
C8 C9 H9 116.8(12) . . ?
O4 C10 C5 113.23(13) . . ?
O4 C10 H10A 108.9 . . ?
C5 C10 H10A 108.9 . . ?
O4 C10 H10B 108.9 . . ?
C5 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?

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 N1 C1 O1 -174.10(17) . . . . ?
C2 N1 C1 N2 7.2(2) . . . . ?
C4 N2 C1 O1 177.25(16) . . . . ?
C9 N2 C1 O1 -0.3(2) . . . . ?
C4 N2 C1 N1 -4.0(2) . . . . ?
C9 N2 C1 N1 178.43(15) . . . . ?
C1 N1 C2 O2 178.76(16) . . . . ?
C1 N1 C2 C3 -3.9(2) . . . . ?
O2 C2 C3 C4 174.53(17) . . . . ?
N1 C2 C3 C4 -2.7(2) . . . . ?
C2 C3 C4 N2 5.5(3) . . . . ?
C2 C3 C4 C5 -168.00(16) . . . . ?
C1 N2 C4 C3 -2.0(3) . . . . ?
C9 N2 C4 C3 175.50(16) . . . . ?
C1 N2 C4 C5 171.76(14) . . . . ?
C9 N2 C4 C5 -10.8(2) . . . . ?
C3 C4 C5 C6 -170.66(17) . . . . ?
N2 C4 C5 C6 15.6(2) . . . . ?
C3 C4 C5 C10 68.3(2) . . . . ?
N2 C4 C5 C10 -105.45(17) . . . . ?
C9 O3 C6 C5 78.40(15) . . . . ?
C9 O3 C6 C7 -42.17(16) . . . . ?
C4 C5 C6 O3 -48.95(17) . . . . ?
C10 C5 C6 O3 70.19(18) . . . . ?
C4 C5 C6 C7 66.42(19) . . . . ?
C10 C5 C6 C7 -174.44(14) . . . . ?
O3 C6 C7 O5 -98.75(17) . . . . ?
C5 C6 C7 O5 144.81(15) . . . . ?
O3 C6 C7 C8 19.03(18) . . . . ?
C5 C6 C7 C8 -97.40(17) . . . . ?
O5 C7 C8 C9 127.49(16) . . . . ?
C6 C7 C8 C9 9.33(18) . . . . ?
C6 O3 C9 N2 -71.34(16) . . . . ?
C6 O3 C9 C8 48.37(17) . . . . ?
C4 N2 C9 O3 39.0(2) . . . . ?
C1 N2 C9 O3 -143.44(15) . . . . ?
C4 N2 C9 C8 -74.68(19) . . . . ?
C1 N2 C9 C8 102.91(17) . . . . ?
C7 C8 C9 O3 -35.37(18) . . . . ?
C7 C8 C9 N2 80.83(17) . . . . ?
C4 C5 C10 O4 179.19(15) . . . . ?
C6 C5 C10 O4 57.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4O O5 0.81(3) 1.99(3) 2.803(2) 177(3) 2_645
O5 H5O O4 0.78(3) 2.04(3) 2.793(2) 163(3) 2_645
N1 H1N O2 0.82(2) 2.07(3) 2.885(2) 170(3) 2_556

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        66.17
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 1003705'
