# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Larry McLaughlin'

_publ_contact_author_email       larry.mclaughlin@bc.edu
_publ_author_name                'Larry McLaughlin'
# Attachment '- REC_dU.cif'

data_C10H12N2O5
_database_code_depnum_ccdc_archive 'CCDC 882419'
#TrackingRef '- REC_dU.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H12 N2 O5), (H2 O)'
_chemical_formula_sum            'C20 H26 N4 O11'
_chemical_formula_weight         498.45

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.8443(6)
_cell_length_b                   12.9861(9)
_cell_length_c                   18.0290(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2070.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      67.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    none
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8055
_exptl_absorpt_correction_T_max  0.9150
_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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11792
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.20
_diffrn_reflns_theta_max         67.73
_reflns_number_total             3655
_reflns_number_gt                3572
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0359P)^2^+0.4788P] where P=(Fo^2^+2Fc^2^)/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 ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(11)
_refine_ls_number_reflns         3655
_refine_ls_number_parameters     366
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.051
_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 0.41036(13) 0.63252(8) 0.18952(6) 0.0198(2) Uani 1 1 d . . .
O2 O 0.60347(13) 0.93286(9) 0.10457(6) 0.0182(2) Uani 1 1 d . . .
O3 O 0.17885(13) 0.99160(8) 0.42898(6) 0.0169(2) Uani 1 1 d D . .
H3O H 0.0901(18) 1.0077(16) 0.4337(12) 0.025 Uiso 1 1 d D . .
O4 O 0.12944(13) 0.68558(9) 0.47688(6) 0.0183(2) Uani 1 1 d D . .
H4O H 0.168(2) 0.6674(16) 0.5162(9) 0.027 Uiso 1 1 d D . .
O5 O 0.14743(11) 0.75411(8) 0.32036(6) 0.0138(2) Uani 1 1 d . . .
N1 N 0.51519(15) 0.78220(10) 0.15124(7) 0.0155(3) Uani 1 1 d D . .
H1N H 0.548(2) 0.7476(14) 0.1132(9) 0.019 Uiso 1 1 d D . .
N2 N 0.39015(15) 0.77332(10) 0.26605(7) 0.0148(3) Uani 1 1 d . . .
C1 C 0.43506(17) 0.72328(12) 0.20116(9) 0.0157(3) Uani 1 1 d . . .
C2 C 0.53672(17) 0.88707(12) 0.15497(8) 0.0151(3) Uani 1 1 d . . .
C3 C 0.47993(17) 0.93450(12) 0.22153(8) 0.0157(3) Uani 1 1 d . . .
H1 H 0.4907 1.0067 0.2279 0.019 Uiso 1 1 calc R . .
C4 C 0.41204(16) 0.87894(12) 0.27480(8) 0.0145(3) Uani 1 1 d . . .
C5 C 0.36509(18) 0.93047(12) 0.34634(8) 0.0154(3) Uani 1 1 d . . .
H5A H 0.3948 1.0039 0.3436 0.018 Uiso 1 1 calc R . .
H5B H 0.4235 0.8990 0.3873 0.018 Uiso 1 1 calc R . .
C6 C 0.19752(17) 0.92547(12) 0.36657(8) 0.0148(3) Uani 1 1 d D . .
H6 H 0.137(2) 0.9521(14) 0.3240(9) 0.018 Uiso 1 1 d D . .
C7 C 0.13951(17) 0.81793(12) 0.38574(8) 0.0144(3) Uani 1 1 d D . .
H7 H 0.0327(17) 0.8241(14) 0.4018(10) 0.017 Uiso 1 1 d D . .
C8 C 0.22977(17) 0.75953(12) 0.44375(8) 0.0155(3) Uani 1 1 d D . .
H8 H 0.268(2) 0.8068(13) 0.4824(9) 0.019 Uiso 1 1 d D . .
C9 C 0.35338(17) 0.70599(12) 0.39757(8) 0.0169(3) Uani 1 1 d . . .
H9A H 0.4514 0.7420 0.4028 0.020 Uiso 1 1 calc R . .
H9B H 0.3660 0.6334 0.4132 0.020 Uiso 1 1 calc R . .
C10 C 0.29547(17) 0.71238(12) 0.31717(9) 0.0152(3) Uani 1 1 d D . .
H10 H 0.293(2) 0.6446(12) 0.2934(10) 0.018 Uiso 1 1 d D . .
O6 O 0.88626(15) 0.63918(8) 0.21819(6) 0.0216(3) Uani 1 1 d . . .
O7 O 0.73067(13) 0.87560(9) 0.38641(6) 0.0184(2) Uani 1 1 d . . .
O8 O 1.13265(13) 1.10031(8) 0.09315(6) 0.0162(2) Uani 1 1 d D . .
H8O H 1.0507(19) 1.1180(16) 0.0727(11) 0.024 Uiso 1 1 d D . .
O9 O 1.14588(12) 0.84199(8) -0.04100(6) 0.0162(2) Uani 1 1 d D . .
H9O H 1.209(2) 0.8841(14) -0.0568(11) 0.024 Uiso 1 1 d D . .
O10 O 1.16061(12) 0.82376(8) 0.12857(6) 0.0152(2) Uani 1 1 d . . .
N3 N 0.80289(15) 0.75979(10) 0.29928(7) 0.0157(3) Uani 1 1 d D . .
H3N H 0.792(2) 0.7110(13) 0.3296(10) 0.019 Uiso 1 1 d D . .
N4 N 0.92132(14) 0.80938(10) 0.18826(7) 0.0144(3) Uani 1 1 d . . .
C11 C 0.87222(17) 0.72987(12) 0.23378(8) 0.0161(3) Uani 1 1 d . . .
C12 C 0.78522(17) 0.85866(12) 0.32403(8) 0.0156(3) Uani 1 1 d . . .
C13 C 0.83479(17) 0.93654(12) 0.27358(8) 0.0155(3) Uani 1 1 d . . .
H13 H 0.8212 1.0070 0.2862 0.019 Uiso 1 1 calc R . .
C14 C 0.90063(17) 0.91188(12) 0.20831(8) 0.0145(3) Uani 1 1 d . . .
C15 C 0.94390(17) 0.99688(11) 0.15555(8) 0.0149(3) Uani 1 1 d . . .
H15A H 0.9161 1.0632 0.1789 0.018 Uiso 1 1 calc R . .
H15B H 0.8810 0.9895 0.1104 0.018 Uiso 1 1 calc R . .
C16 C 1.10939(18) 1.00439(12) 0.13100(8) 0.0145(3) Uani 1 1 d D . .
H16 H 1.1734(19) 1.0051(14) 0.1752(9) 0.017 Uiso 1 1 d D . .
C17 C 1.16225(17) 0.91475(11) 0.08315(8) 0.0146(3) Uani 1 1 d D . .
H17 H 1.2666(17) 0.9254(14) 0.0663(10) 0.017 Uiso 1 1 d D . .
C18 C 1.06036(17) 0.88956(12) 0.01700(8) 0.0146(3) Uani 1 1 d D . .
H18 H 1.004(2) 0.9513(12) -0.0005(10) 0.018 Uiso 1 1 d D . .
C19 C 0.94936(17) 0.81017(12) 0.04813(8) 0.0168(3) Uani 1 1 d . . .
H19A H 0.9412 0.7501 0.0146 0.020 Uiso 1 1 calc R . .
H19B H 0.8477 0.8409 0.0546 0.020 Uiso 1 1 calc R . .
C20 C 1.01616(18) 0.77820(11) 0.12342(9) 0.0157(3) Uani 1 1 d D . .
H20 H 1.031(2) 0.7024(11) 0.1288(10) 0.019 Uiso 1 1 d D . .
O1S O 0.11071(14) 0.54924(9) 0.05008(7) 0.0233(3) Uani 1 1 d D . .
H1S H 0.181(2) 0.5056(16) 0.0634(14) 0.044(7) Uiso 1 1 d D . .
H2S H 0.125(3) 0.5565(18) 0.0040(9) 0.038(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
O1 0.0267(6) 0.0127(5) 0.0201(5) -0.0013(4) 0.0047(5) 0.0002(4)
O2 0.0194(5) 0.0187(5) 0.0165(5) 0.0020(4) 0.0024(5) -0.0037(5)
O3 0.0154(5) 0.0184(5) 0.0170(5) -0.0041(4) 0.0019(4) -0.0001(5)
O4 0.0191(5) 0.0218(5) 0.0138(5) 0.0051(4) -0.0012(4) -0.0044(5)
O5 0.0121(5) 0.0153(5) 0.0139(5) -0.0014(4) -0.0002(4) -0.0005(4)
N1 0.0166(6) 0.0153(6) 0.0145(6) -0.0020(5) 0.0016(5) 0.0003(5)
N2 0.0154(6) 0.0138(6) 0.0151(6) -0.0003(5) 0.0011(5) 0.0007(5)
C1 0.0144(7) 0.0163(8) 0.0164(7) 0.0003(6) -0.0009(6) 0.0019(6)
C2 0.0115(7) 0.0174(7) 0.0164(7) 0.0007(6) -0.0028(6) -0.0006(6)
C3 0.0138(7) 0.0150(7) 0.0183(7) -0.0015(6) -0.0012(6) -0.0007(6)
C4 0.0111(7) 0.0143(7) 0.0179(7) -0.0016(6) -0.0026(6) 0.0001(6)
C5 0.0163(8) 0.0139(7) 0.0159(7) -0.0025(6) 0.0008(6) -0.0028(6)
C6 0.0159(8) 0.0153(7) 0.0131(7) -0.0016(6) 0.0008(6) 0.0003(6)
C7 0.0140(7) 0.0171(7) 0.0121(6) -0.0021(6) 0.0012(6) -0.0017(6)
C8 0.0147(7) 0.0163(7) 0.0155(7) -0.0003(6) -0.0007(6) -0.0020(6)
C9 0.0159(7) 0.0178(7) 0.0168(7) 0.0020(6) -0.0004(6) 0.0001(6)
C10 0.0149(7) 0.0137(7) 0.0171(7) 0.0001(6) -0.0004(6) 0.0001(6)
O6 0.0331(7) 0.0133(6) 0.0184(5) -0.0001(4) 0.0026(5) -0.0024(5)
O7 0.0206(6) 0.0205(6) 0.0143(5) 0.0020(4) 0.0036(4) 0.0015(4)
O8 0.0183(5) 0.0128(5) 0.0175(5) 0.0016(4) 0.0019(4) -0.0017(4)
O9 0.0182(5) 0.0160(5) 0.0143(5) -0.0023(4) 0.0031(4) -0.0030(4)
O10 0.0139(5) 0.0139(5) 0.0176(5) 0.0018(4) -0.0006(4) 0.0008(4)
N3 0.0180(6) 0.0145(6) 0.0145(6) 0.0046(5) -0.0005(5) -0.0017(5)
N4 0.0153(6) 0.0144(6) 0.0134(6) -0.0006(5) -0.0002(5) -0.0008(5)
C11 0.0151(7) 0.0163(8) 0.0168(7) 0.0000(6) -0.0028(6) -0.0011(6)
C12 0.0118(7) 0.0186(7) 0.0163(7) 0.0006(6) -0.0029(6) 0.0012(6)
C13 0.0138(7) 0.0151(7) 0.0177(7) 0.0003(6) -0.0018(6) 0.0013(6)
C14 0.0113(7) 0.0153(7) 0.0170(7) 0.0003(6) -0.0027(6) 0.0005(6)
C15 0.0159(8) 0.0133(7) 0.0155(7) -0.0005(6) 0.0008(6) 0.0020(6)
C16 0.0153(7) 0.0142(7) 0.0139(7) -0.0005(6) 0.0005(6) -0.0003(6)
C17 0.0134(7) 0.0143(7) 0.0159(7) 0.0010(6) 0.0015(6) -0.0010(6)
C18 0.0157(7) 0.0140(7) 0.0141(7) -0.0022(6) 0.0007(6) 0.0012(6)
C19 0.0184(8) 0.0176(7) 0.0145(7) -0.0022(6) 0.0000(6) -0.0038(6)
C20 0.0164(7) 0.0136(7) 0.0169(7) -0.0025(6) 0.0009(6) -0.0001(6)
O1S 0.0237(6) 0.0270(6) 0.0191(6) 0.0038(5) 0.0033(5) 0.0012(5)

_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 1.2170(19) . ?
O2 C2 1.236(2) . ?
O3 C6 1.4250(18) . ?
O3 H3O 0.817(15) . ?
O4 C8 1.4374(19) . ?
O4 H4O 0.821(16) . ?
O5 C10 1.4182(18) . ?
O5 C7 1.4427(17) . ?
N1 C2 1.377(2) . ?
N1 C1 1.377(2) . ?
N1 H1N 0.868(15) . ?
N2 C4 1.394(2) . ?
N2 C1 1.396(2) . ?
N2 C10 1.4754(19) . ?
C2 C3 1.439(2) . ?
C3 C4 1.343(2) . ?
C3 H1 0.9500 . ?
C4 C5 1.511(2) . ?
C5 C6 1.528(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.527(2) . ?
C6 H6 0.999(14) . ?
C7 C8 1.519(2) . ?
C7 H7 0.991(14) . ?
C8 C9 1.540(2) . ?
C8 H8 0.988(14) . ?
C9 C10 1.540(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 0.978(14) . ?
O6 C11 1.2171(19) . ?
O7 C12 1.2433(19) . ?
O8 C16 1.4353(18) . ?
O8 H8O 0.845(15) . ?
O9 C18 1.4308(18) . ?
O9 H9O 0.834(15) . ?
O10 C20 1.4110(19) . ?
O10 C17 1.4377(18) . ?
N3 C12 1.368(2) . ?
N3 C11 1.386(2) . ?
N3 H3N 0.843(15) . ?
N4 C11 1.389(2) . ?
N4 C14 1.391(2) . ?
N4 C20 1.4948(19) . ?
C12 C13 1.429(2) . ?
C13 C14 1.351(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.506(2) . ?
C15 C16 1.532(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(2) . ?
C16 H16 0.978(14) . ?
C17 C18 1.530(2) . ?
C17 H17 0.982(14) . ?
C18 C19 1.530(2) . ?
C18 H18 0.994(14) . ?
C19 C20 1.537(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20 0.997(14) . ?
O1S H1S 0.872(16) . ?
O1S H2S 0.845(16) . ?

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
C6 O3 H3O 110.4(15) . . ?
C8 O4 H4O 107.1(15) . . ?
C10 O5 C7 107.30(11) . . ?
C2 N1 C1 126.06(13) . . ?
C2 N1 H1N 120.3(13) . . ?
C1 N1 H1N 113.5(13) . . ?
C4 N2 C1 120.88(13) . . ?
C4 N2 C10 122.40(12) . . ?
C1 N2 C10 115.81(12) . . ?
O1 C1 N1 121.18(14) . . ?
O1 C1 N2 122.97(14) . . ?
N1 C1 N2 115.81(13) . . ?
O2 C2 N1 120.40(14) . . ?
O2 C2 C3 125.01(14) . . ?
N1 C2 C3 114.57(14) . . ?
C4 C3 C2 121.49(14) . . ?
C4 C3 H1 119.3 . . ?
C2 C3 H1 119.3 . . ?
C3 C4 N2 120.64(14) . . ?
C3 C4 C5 119.69(14) . . ?
N2 C4 C5 119.61(13) . . ?
C4 C5 C6 116.84(13) . . ?
C4 C5 H5A 108.1 . . ?
C6 C5 H5A 108.1 . . ?
C4 C5 H5B 108.1 . . ?
C6 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
O3 C6 C7 109.48(12) . . ?
O3 C6 C5 105.98(12) . . ?
C7 C6 C5 114.76(13) . . ?
O3 C6 H6 109.6(11) . . ?
C7 C6 H6 108.0(11) . . ?
C5 C6 H6 108.9(11) . . ?
O5 C7 C8 104.49(12) . . ?
O5 C7 C6 108.91(11) . . ?
C8 C7 C6 115.84(12) . . ?
O5 C7 H7 109.3(11) . . ?
C8 C7 H7 109.9(11) . . ?
C6 C7 H7 108.2(11) . . ?
O4 C8 C7 107.18(12) . . ?
O4 C8 C9 111.17(12) . . ?
C7 C8 C9 103.08(12) . . ?
O4 C8 H8 109.4(11) . . ?
C7 C8 H8 110.8(11) . . ?
C9 C8 H8 114.9(11) . . ?
C10 C9 C8 104.39(12) . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
O5 C10 N2 110.14(12) . . ?
O5 C10 C9 106.83(12) . . ?
N2 C10 C9 115.36(12) . . ?
O5 C10 H10 109.8(11) . . ?
N2 C10 H10 102.9(11) . . ?
C9 C10 H10 111.8(11) . . ?
C16 O8 H8O 108.7(14) . . ?
C18 O9 H9O 108.9(14) . . ?
C20 O10 C17 108.44(11) . . ?
C12 N3 C11 126.25(13) . . ?
C12 N3 H3N 118.7(13) . . ?
C11 N3 H3N 113.2(13) . . ?
C11 N4 C14 121.11(12) . . ?
C11 N4 C20 115.87(12) . . ?
C14 N4 C20 122.42(12) . . ?
O6 C11 N3 120.87(14) . . ?
O6 C11 N4 123.44(14) . . ?
N3 C11 N4 115.69(13) . . ?
O7 C12 N3 120.35(14) . . ?
O7 C12 C13 124.72(15) . . ?
N3 C12 C13 114.92(14) . . ?
C14 C13 C12 121.25(15) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 N4 120.63(14) . . ?
C13 C14 C15 119.05(14) . . ?
N4 C14 C15 120.23(13) . . ?
C14 C15 C16 118.14(12) . . ?
C14 C15 H15A 107.8 . . ?
C16 C15 H15A 107.8 . . ?
C14 C15 H15B 107.8 . . ?
C16 C15 H15B 107.8 . . ?
H15A C15 H15B 107.1 . . ?
O8 C16 C17 110.49(12) . . ?
O8 C16 C15 109.24(12) . . ?
C17 C16 C15 114.10(13) . . ?
O8 C16 H16 107.2(11) . . ?
C17 C16 H16 107.0(11) . . ?
C15 C16 H16 108.5(11) . . ?
O10 C17 C16 107.61(12) . . ?
O10 C17 C18 105.20(11) . . ?
C16 C17 C18 115.11(13) . . ?
O10 C17 H17 107.6(11) . . ?
C16 C17 H17 110.9(11) . . ?
C18 C17 H17 110.0(11) . . ?
O9 C18 C17 110.52(12) . . ?
O9 C18 C19 108.44(12) . . ?
C17 C18 C19 103.65(12) . . ?
O9 C18 H18 112.3(11) . . ?
C17 C18 H18 111.7(11) . . ?
C19 C18 H18 109.9(11) . . ?
C18 C19 C20 105.02(12) . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C20 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
O10 C20 N4 110.06(12) . . ?
O10 C20 C19 107.03(12) . . ?
N4 C20 C19 113.68(12) . . ?
O10 C20 H20 106.9(11) . . ?
N4 C20 H20 105.3(11) . . ?
C19 C20 H20 113.7(11) . . ?
H1S O1S H2S 104(2) . . ?

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 173.07(15) . . . . ?
C2 N1 C1 N2 -9.2(2) . . . . ?
C4 N2 C1 O1 -175.70(14) . . . . ?
C10 N2 C1 O1 -6.4(2) . . . . ?
C4 N2 C1 N1 6.6(2) . . . . ?
C10 N2 C1 N1 175.98(13) . . . . ?
C1 N1 C2 O2 -175.75(14) . . . . ?
C1 N1 C2 C3 5.9(2) . . . . ?
O2 C2 C3 C4 -178.17(15) . . . . ?
N1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 N2 -2.1(2) . . . . ?
C2 C3 C4 C5 175.23(14) . . . . ?
C1 N2 C4 C3 -1.5(2) . . . . ?
C10 N2 C4 C3 -170.08(14) . . . . ?
C1 N2 C4 C5 -178.75(13) . . . . ?
C10 N2 C4 C5 12.6(2) . . . . ?
C3 C4 C5 C6 121.39(16) . . . . ?
N2 C4 C5 C6 -61.29(19) . . . . ?
C4 C5 C6 O3 -171.45(12) . . . . ?
C4 C5 C6 C7 67.62(17) . . . . ?
C10 O5 C7 C8 -38.58(14) . . . . ?
C10 O5 C7 C6 85.79(14) . . . . ?
O3 C6 C7 O5 175.31(11) . . . . ?
C5 C6 C7 O5 -65.70(16) . . . . ?
O3 C6 C7 C8 -67.31(16) . . . . ?
C5 C6 C7 C8 51.67(17) . . . . ?
O5 C7 C8 O4 -84.52(13) . . . . ?
C6 C7 C8 O4 155.67(12) . . . . ?
O5 C7 C8 C9 32.86(14) . . . . ?
C6 C7 C8 C9 -86.95(15) . . . . ?
O4 C8 C9 C10 98.41(14) . . . . ?
C7 C8 C9 C10 -16.12(15) . . . . ?
C7 O5 C10 N2 -98.17(13) . . . . ?
C7 O5 C10 C9 27.82(14) . . . . ?
C4 N2 C10 O5 56.57(18) . . . . ?
C1 N2 C10 O5 -112.58(14) . . . . ?
C4 N2 C10 C9 -64.44(18) . . . . ?
C1 N2 C10 C9 126.41(14) . . . . ?
C8 C9 C10 O5 -6.18(15) . . . . ?
C8 C9 C10 N2 116.61(14) . . . . ?
C12 N3 C11 O6 177.58(15) . . . . ?
C12 N3 C11 N4 -3.1(2) . . . . ?
C14 N4 C11 O6 179.13(15) . . . . ?
C20 N4 C11 O6 -9.5(2) . . . . ?
C14 N4 C11 N3 -0.1(2) . . . . ?
C20 N4 C11 N3 171.20(13) . . . . ?
C11 N3 C12 O7 -174.77(14) . . . . ?
C11 N3 C12 C13 4.7(2) . . . . ?
O7 C12 C13 C14 176.31(15) . . . . ?
N3 C12 C13 C14 -3.1(2) . . . . ?
C12 C13 C14 N4 0.3(2) . . . . ?
C12 C13 C14 C15 177.06(14) . . . . ?
C11 N4 C14 C13 1.4(2) . . . . ?
C20 N4 C14 C13 -169.36(14) . . . . ?
C11 N4 C14 C15 -175.30(14) . . . . ?
C20 N4 C14 C15 13.9(2) . . . . ?
C13 C14 C15 C16 122.93(15) . . . . ?
N4 C14 C15 C16 -60.32(19) . . . . ?
C14 C15 C16 O8 -168.98(12) . . . . ?
C14 C15 C16 C17 66.81(17) . . . . ?
C20 O10 C17 C16 89.00(14) . . . . ?
C20 O10 C17 C18 -34.20(15) . . . . ?
O8 C16 C17 O10 170.18(11) . . . . ?
C15 C16 C17 O10 -66.28(15) . . . . ?
O8 C16 C17 C18 -72.92(16) . . . . ?
C15 C16 C17 C18 50.62(17) . . . . ?
O10 C17 C18 O9 -88.41(14) . . . . ?
C16 C17 C18 O9 153.33(12) . . . . ?
O10 C17 C18 C19 27.60(15) . . . . ?
C16 C17 C18 C19 -90.66(14) . . . . ?
O9 C18 C19 C20 105.41(13) . . . . ?
C17 C18 C19 C20 -12.06(15) . . . . ?
C17 O10 C20 N4 -97.74(13) . . . . ?
C17 O10 C20 C19 26.25(15) . . . . ?
C11 N4 C20 O10 -118.74(14) . . . . ?
C14 N4 C20 O10 52.47(18) . . . . ?
C11 N4 C20 C19 121.22(14) . . . . ?
C14 N4 C20 C19 -67.57(17) . . . . ?
C18 C19 C20 O10 -7.70(15) . . . . ?
C18 C19 C20 N4 114.04(13) . . . . ?

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
O3 H3O O1S 0.817(15) 1.879(16) 2.6947(16) 176(2) 3
O4 H4O O7 0.821(16) 1.925(16) 2.7401(15) 172(2) 2_466
N1 H1N O9 0.868(15) 1.950(15) 2.8084(17) 169.4(18) 2_465
O8 H8O O4 0.845(15) 2.027(16) 2.8623(16) 170(2) 3_655
O9 H9O O3 0.834(15) 1.910(16) 2.7139(15) 161(2) 4_674
N3 H3N O8 0.843(15) 2.111(16) 2.8940(17) 154.4(18) 3_745
O1S H1S O7 0.872(16) 2.070(18) 2.8920(17) 157(2) 3_645
O1S H2S O2 0.845(16) 1.972(17) 2.7986(16) 166(2) 2_465

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        67.73
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038