# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_dh_ab
_database_code_depnum_ccdc_archive 'CCDC 1013044'
_audit_update_record             
;
2014-07-09 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N3 O7'
_chemical_formula_sum            'C12 H13 N3 O7'
_chemical_formula_weight         311.25

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   'P2(1)/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                   10.056(10)
_cell_length_b                   15.875(16)
_cell_length_c                   9.709(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.617(15)
_cell_angle_gamma                90.00
_cell_volume                     1398(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2243
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.50

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.195
_exptl_crystal_density_meas      1.479
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.0
_exptl_crystal_F_000'            648.41
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   '(SADABS; BRUKER, 2008)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10755
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2567
_reflns_number_gt                1647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1682P)²+2.0250P] 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     SHELXL
_refine_ls_extinction_coef       0.031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2526
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.249
_refine_ls_wR_factor_gt          0.2625
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 1.0385(4) 0.1120(3) 1.2511(4) 0.0541(11) Uani 1 1 d . . .
O2 O 0.4192(6) 0.2756(3) 0.3910(5) 0.0835(16) Uani 1 1 d . . .
O3 O 0.8165(4) 0.2862(2) 1.0943(3) 0.0430(9) Uani 1 1 d . . .
O4 O 0.4137(6) 0.5880(3) 0.7681(5) 0.0877(17) Uani 1 1 d . . .
O5 O 0.6078(5) 0.5668(3) 0.9775(5) 0.0665(13) Uani 1 1 d . . .
O6 O 0.3123(5) 0.3961(3) 0.3453(4) 0.0682(13) Uani 1 1 d . . .
O7 O 0.8028(4) 0.0941(3) 1.0838(4) 0.0534(11) Uani 1 1 d . . .
N1 N 0.8439(4) 0.2206(2) 0.9041(4) 0.0344(10) Uani 1 1 d . . .
H1 H 0.8109 0.2148 0.8068 0.041 Uiso 1 1 calc R . .
N2 N 0.3961(5) 0.3442(3) 0.4312(5) 0.0507(12) Uani 1 1 d . . .
N3 N 0.5201(5) 0.5458(3) 0.8499(5) 0.0523(12) Uani 1 1 d . . .
C1 C 1.0122(7) 0.0633(4) 1.3622(7) 0.0641(18) Uani 1 1 d . . .
H1A H 0.9284 0.0858 1.3727 0.096 Uiso 1 1 calc R . .
H1B H 1.0974 0.0660 1.4589 0.096 Uiso 1 1 calc R . .
H1C H 0.9933 0.0058 1.3291 0.096 Uiso 1 1 calc R . .
C2 C 0.9230(6) 0.1225(3) 1.1157(5) 0.0391(12) Uani 1 1 d . . .
C3 C 0.9688(5) 0.1684(3) 1.0046(5) 0.0354(11) Uani 1 1 d . . .
C4 C 0.7800(5) 0.2765(3) 0.9581(5) 0.0300(10) Uani 1 1 d . . .
C5 C 0.6628(5) 0.3310(3) 0.8425(5) 0.0333(11) Uani 1 1 d . . .
C6 C 0.5804(5) 0.3094(3) 0.6909(5) 0.0347(11) Uani 1 1 d . . .
H6 H 0.5923 0.2569 0.6549 0.042 Uiso 1 1 calc R . .
C7 C 0.4801(5) 0.3669(3) 0.5934(5) 0.0372(11) Uani 1 1 d . . .
C8 C 1.1066(6) 0.2222(4) 1.0825(6) 0.0525(14) Uani 1 1 d . . .
H8A H 1.1287 0.2493 1.0065 0.079 Uiso 1 1 calc R . .
H8B H 1.1880 0.1871 1.1455 0.079 Uiso 1 1 calc R . .
H8C H 1.0901 0.2641 1.1448 0.079 Uiso 1 1 calc R . .
C9 C 0.6409(5) 0.4090(3) 0.8945(5) 0.0364(11) Uani 1 1 d . . .
H9 H 0.6941 0.4241 0.9964 0.044 Uiso 1 1 calc R . .
C10 C 0.5393(5) 0.4634(3) 0.7930(5) 0.0393(12) Uani 1 1 d . . .
C11 C 0.4556(5) 0.4447(3) 0.6405(5) 0.0403(12) Uani 1 1 d . . .
H11 H 0.3871 0.4824 0.5740 0.048 Uiso 1 1 calc R . .
C12 C 0.9931(6) 0.1016(4) 0.9057(6) 0.0498(14) Uani 1 1 d . . .
H12A H 0.9061 0.0676 0.8583 0.075 Uiso 1 1 calc R . .
H12B H 1.0751 0.0667 0.9680 0.075 Uiso 1 1 calc R . .
H12C H 1.0136 0.1284 0.8283 0.075 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 C2 1.336(6) . ?
O1 C1 1.442(7) . ?
O2 N2 1.213(6) . ?
O3 C4 1.220(5) . ?
O4 N3 1.221(6) . ?
O5 N3 1.216(6) . ?
O6 N2 1.215(6) . ?
O7 C2 1.198(6) . ?
N1 C4 1.328(5) . ?
N1 C3 1.469(6) . ?
N1 H1 0.8600 . ?
N2 C7 1.474(6) . ?
N3 C10 1.465(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.529(7) . ?
C3 C12 1.520(7) . ?
C3 C8 1.522(7) . ?
C4 C5 1.502(6) . ?
C5 C6 1.385(6) . ?
C5 C9 1.390(7) . ?
C6 C7 1.387(7) . ?
C6 H6 0.9300 . ?
C7 C11 1.375(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.375(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(7) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C2 O1 C1 116.1(4) . . ?
C4 N1 C3 122.3(4) . . ?
C4 N1 H1 118.8 . . ?
C3 N1 H1 118.8 . . ?
O2 N2 O6 124.1(5) . . ?
O2 N2 C7 117.5(4) . . ?
O6 N2 C7 118.3(5) . . ?
O5 N3 O4 123.9(5) . . ?
O5 N3 C10 118.2(4) . . ?
O4 N3 C10 117.8(5) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O7 C2 O1 123.9(5) . . ?
O7 C2 C3 125.1(4) . . ?
O1 C2 C3 110.8(4) . . ?
N1 C3 C12 107.4(4) . . ?
N1 C3 C8 110.3(4) . . ?
C12 C3 C8 110.1(4) . . ?
N1 C3 C2 107.8(4) . . ?
C12 C3 C2 107.0(4) . . ?
C8 C3 C2 113.8(4) . . ?
O3 C4 N1 122.9(4) . . ?
O3 C4 C5 120.6(4) . . ?
N1 C4 C5 116.5(4) . . ?
C6 C5 C9 119.4(4) . . ?
C6 C5 C4 124.6(4) . . ?
C9 C5 C4 116.0(4) . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C11 C7 C6 123.1(4) . . ?
C11 C7 N2 118.2(4) . . ?
C6 C7 N2 118.7(4) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C5 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C5 C9 H9 120.5 . . ?
C9 C10 C11 123.5(5) . . ?
C9 C10 N3 118.0(4) . . ?
C11 C10 N3 118.5(4) . . ?
C7 C11 C10 115.8(4) . . ?
C7 C11 H11 122.1 . . ?
C10 C11 H11 122.1 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_asp1
_database_code_depnum_ccdc_archive 'CCDC 1013045'
_audit_update_record             
;
2014-07-09 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N3 O9'
_chemical_formula_sum            'C13 H13 N3 O9'
_chemical_formula_weight         355.26
_chemical_absolute_configuration syn

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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   4.895(2)
_cell_length_b                   12.127(12)
_cell_length_c                   27.29(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1620.0(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1120
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      17.95

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.195
_exptl_crystal_density_meas      1.457
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_crystal_F_000'            736.50
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   '(SADABS; BRUKER, 2008)'

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14108
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3538
_reflns_number_gt                1799
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0000P)²+1.8251P] 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     SHELXL
_refine_ls_extinction_coef       0.0019(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(3)
_refine_ls_number_reflns         3345
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_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 0.7017(11) 0.2364(4) 0.39496(14) 0.0976(17) Uani 1 1 d . . .
O2 O 0.3441(11) 0.3479(4) 0.06004(15) 0.0938(16) Uani 1 1 d . . .
O3 O 0.3608(11) 0.1374(4) 0.36920(15) 0.1007(18) Uani 1 1 d . . .
O4 O 1.2634(8) 0.4380(3) 0.27448(14) 0.0644(11) Uani 1 1 d . . .
O5 O 1.0808(10) 0.4640(4) 0.20325(15) 0.0928(16) Uani 1 1 d . . .
O6 O 0.1867(8) 0.0984(3) 0.18988(13) 0.0619(11) Uani 1 1 d . . .
O7 O 0.0236(10) 0.2448(4) 0.09463(18) 0.0966(16) Uani 1 1 d . . .
O8 O 0.5675(10) -0.0608(3) 0.03899(13) 0.0797(13) Uani 1 1 d . . .
O9 O 0.8204(10) -0.0578(4) 0.10712(16) 0.0931(16) Uani 1 1 d . . .
N1 N 0.5575(13) 0.1980(4) 0.36218(17) 0.0691(15) Uani 1 1 d . . .
N2 N 0.5597(9) 0.1265(3) 0.14145(13) 0.0486(12) Uani 1 1 d . . .
H2 H 0.7216 0.1538 0.1400 0.058 Uiso 1 1 calc R . .
N3 N 1.0909(10) 0.4187(4) 0.24330(18) 0.0556(12) Uani 1 1 d . . .
C1 C 0.6311(10) 0.2270(4) 0.31032(17) 0.0451(13) Uani 1 1 d . . .
C2 C 0.4943(10) 0.1730(4) 0.27275(18) 0.0488(14) Uani 1 1 d . . .
H2A H 0.3605 0.1209 0.2797 0.059 Uiso 1 1 calc R . .
C3 C 0.5610(10) 0.1984(4) 0.22427(17) 0.0397(11) Uani 1 1 d . . .
C4 C 0.4183(11) 0.1354(4) 0.18368(18) 0.0464(13) Uani 1 1 d . . .
C5 C 0.4486(11) 0.0725(4) 0.09808(16) 0.0501(14) Uani 1 1 d . . .
H5 H 0.2694 0.0419 0.1065 0.060 Uiso 1 1 calc R . .
C6 C 0.4099(12) 0.1567(5) 0.05594(19) 0.0637(16) Uani 1 1 d . . .
H6A H 0.5870 0.1834 0.0453 0.076 Uiso 1 1 calc R . .
H6B H 0.3231 0.1206 0.0283 0.076 Uiso 1 1 calc R . .
C7 C 0.2369(15) 0.2525(5) 0.0724(2) 0.0670(17) Uani 1 1 d . . .
C8 C 0.188(2) 0.4450(5) 0.0768(3) 0.142(4) Uani 1 1 d . . .
H8A H -0.0008 0.4359 0.0685 0.213 Uiso 1 1 calc R . .
H8B H 0.2583 0.5100 0.0610 0.213 Uiso 1 1 calc R . .
H8C H 0.2067 0.4524 0.1116 0.213 Uiso 1 1 calc R . .
C9 C 0.7542(10) 0.2818(4) 0.21499(17) 0.0426(12) Uani 1 1 d . . .
H9 H 0.7948 0.3026 0.1830 0.051 Uiso 1 1 calc R . .
C10 C 0.8831(11) 0.3326(4) 0.25428(19) 0.0459(13) Uani 1 1 d . . .
C11 C 0.8280(11) 0.3073(4) 0.30226(19) 0.0499(14) Uani 1 1 d . . .
H11 H 0.9177 0.3421 0.3280 0.060 Uiso 1 1 calc R . .
C12 C 0.6355(13) -0.0227(5) 0.0827(2) 0.0554(16) Uani 1 1 d . . .
C13 C 0.7485(17) -0.1512(5) 0.0220(2) 0.105(3) Uani 1 1 d . . .
H13A H 0.9357 -0.1285 0.0247 0.158 Uiso 1 1 calc R . .
H13B H 0.7079 -0.1682 -0.0116 0.158 Uiso 1 1 calc R . .
H13C H 0.7188 -0.2155 0.0419 0.158 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 N1 1.231(6) . ?
O2 C7 1.314(7) . ?
O2 C8 1.475(8) . ?
O3 N1 1.227(6) . ?
O4 N3 1.221(5) . ?
O5 N3 1.224(5) . ?
O6 C4 1.231(6) . ?
O7 C7 1.212(7) . ?
O8 C12 1.322(6) . ?
O8 C13 1.484(7) . ?
O9 C12 1.202(7) . ?
N1 C1 1.502(6) . ?
N2 C4 1.349(6) . ?
N2 C5 1.458(6) . ?
N2 H2 0.8600 . ?
N3 C10 1.488(6) . ?
C1 C11 1.388(7) . ?
C1 C2 1.389(6) . ?
C2 C3 1.397(6) . ?
C2 H2A 0.9300 . ?
C3 C9 1.408(6) . ?
C3 C4 1.516(7) . ?
C5 C12 1.531(7) . ?
C5 C6 1.550(7) . ?
C5 H5 0.9800 . ?
C6 C7 1.506(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.388(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(6) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 O2 C8 114.7(6) . . ?
C12 O8 C13 112.9(5) . . ?
O3 N1 O1 124.3(5) . . ?
O3 N1 C1 118.4(5) . . ?
O1 N1 C1 117.4(5) . . ?
C4 N2 C5 122.5(4) . . ?
C4 N2 H2 118.7 . . ?
C5 N2 H2 118.7 . . ?
O4 N3 O5 124.3(5) . . ?
O4 N3 C10 117.8(5) . . ?
O5 N3 C10 117.8(5) . . ?
C11 C1 C2 123.3(5) . . ?
C11 C1 N1 118.7(5) . . ?
C2 C1 N1 118.1(5) . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C2 C3 C9 119.1(4) . . ?
C2 C3 C4 118.2(4) . . ?
C9 C3 C4 122.7(4) . . ?
O6 C4 N2 124.1(5) . . ?
O6 C4 C3 120.5(5) . . ?
N2 C4 C3 115.3(4) . . ?
N2 C5 C12 109.8(4) . . ?
N2 C5 C6 110.6(4) . . ?
C12 C5 C6 111.5(4) . . ?
N2 C5 H5 108.3 . . ?
C12 C5 H5 108.3 . . ?
C6 C5 H5 108.3 . . ?
C7 C6 C5 110.9(5) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O7 C7 O2 122.7(7) . . ?
O7 C7 C6 125.0(6) . . ?
O2 C7 C6 112.2(6) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C3 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C3 C9 H9 120.5 . . ?
C11 C10 C9 123.3(5) . . ?
C11 C10 N3 118.9(5) . . ?
C9 C10 N3 117.8(5) . . ?
C10 C11 C1 116.4(5) . . ?
C10 C11 H11 121.8 . . ?
C1 C11 H11 121.8 . . ?
O9 C12 O8 124.5(6) . . ?
O9 C12 C5 124.4(5) . . ?
O8 C12 C5 111.1(5) . . ?
O8 C13 H13A 109.5 . . ?
O8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_sb2
_database_code_depnum_ccdc_archive 'CCDC 1013046'
_audit_update_record             
;
2014-07-09 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N3 O9'
_chemical_formula_sum            'C14 H15 N3 O9'
_chemical_formula_weight         369.29
_chemical_absolute_configuration syn

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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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                   8.759(4)
_cell_length_b                   12.834(5)
_cell_length_c                   30.603(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3440(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.09

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.212
_exptl_crystal_density_meas      1.426
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536.0
_exptl_crystal_F_000'            1537.01
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   '(SADABS; BRUKER, 2008)'

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32554
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.15
_reflns_number_total             6864
_reflns_number_gt                5890
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0936P)²+1.6591P] 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     SHELXL
_refine_ls_extinction_coef       0.0041(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(2)
_refine_ls_number_reflns         6529
_refine_ls_number_parameters     474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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 1.2706(3) 0.7784(2) 0.32837(8) 0.0788(8) Uani 1 1 d . . .
N3 N 0.8320(3) 0.95545(18) 0.14744(7) 0.0447(5) Uani 1 1 d . . .
H3 H 0.8641 0.9017 0.1334 0.054 Uiso 1 1 calc R . .
O7 O 0.8758(3) 1.1974(3) 0.01280(11) 0.0956(10) Uani 1 1 d . . .
O3 O 1.0382(4) 0.8302(3) 0.33793(9) 0.0909(9) Uani 1 1 d . . .
O2 O 1.3716(5) 0.6370(4) 0.18170(13) 0.1368(18) Uani 1 1 d . . .
O4 O 1.2455(5) 0.6942(3) 0.12729(11) 0.1180(14) Uani 1 1 d . . .
O8 O 0.5778(3) 0.86387(18) 0.11303(8) 0.0667(7) Uani 1 1 d . . .
O6 O 1.0889(3) 1.1057(3) 0.01465(12) 0.0993(10) Uani 1 1 d . . .
O5 O 0.8434(3) 1.0459(2) 0.21138(8) 0.0714(7) Uani 1 1 d . . .
O10 O 0.4679(4) 0.9612(2) 0.21396(10) 0.0866(9) Uani 1 1 d . . .
O11 O 0.3289(3) 0.4344(2) 0.09424(11) 0.0853(8) Uani 1 1 d . . .
O12 O 0.3714(3) 0.5560(2) 0.04318(9) 0.0780(8) Uani 1 1 d . . .
O13 O 0.9010(3) 0.57546(19) 0.18603(6) 0.0650(7) Uani 1 1 d . . .
O14 O 0.6969(5) 0.7052(2) 0.37431(8) 0.1015(12) Uani 1 1 d . . .
O15 O 0.8341(4) 0.5892(3) 0.34398(8) 0.0897(10) Uani 1 1 d . . .
O16 O 0.4432(3) 0.9679(2) 0.28405(9) 0.0764(7) Uani 1 1 d . . .
O17 O 0.9789(3) 0.65177(19) 0.04218(7) 0.0648(6) Uani 1 1 d . . .
O18 O 0.9295(3) 0.79108(18) 0.08360(7) 0.0630(6) Uani 1 1 d . . .
N1 N 1.1467(3) 0.8079(2) 0.31490(9) 0.0587(7) Uani 1 1 d . . .
N2 N 1.2744(4) 0.6921(3) 0.16591(12) 0.0768(9) Uani 1 1 d . . .
O9 O 0.4895(3) 1.01477(19) 0.08752(9) 0.0706(7) Uani 1 1 d . . .
N4 N 0.4954(3) 0.9297(2) 0.25069(10) 0.0534(6) Uani 1 1 d . . .
N5 N 0.7579(3) 0.67478(19) 0.14143(7) 0.0472(6) Uani 1 1 d . . .
H5 H 0.6941 0.7256 0.1399 0.057 Uiso 1 1 calc R . .
N6 N 0.7518(3) 0.6645(2) 0.34241(8) 0.0566(7) Uani 1 1 d . . .
C1 C 1.1255(3) 0.8171(2) 0.26665(9) 0.0443(6) Uani 1 1 d . . .
C2 C 1.0214(3) 0.8890(2) 0.25045(9) 0.0415(6) Uani 1 1 d . . .
H2 H 0.9661 0.9315 0.2693 0.050 Uiso 1 1 calc R . .
C3 C 1.0015(3) 0.8961(2) 0.20509(8) 0.0393(5) Uani 1 1 d . . .
C4 C 0.8868(3) 0.9737(2) 0.18823(9) 0.0433(6) Uani 1 1 d . . .
C5 C 0.7206(3) 1.0236(2) 0.12661(10) 0.0479(7) Uani 1 1 d . . .
H5A H 0.6763 1.0664 0.1499 0.058 Uiso 1 1 calc R . .
C6 C 0.7950(4) 1.0994(3) 0.09411(12) 0.0632(8) Uani 1 1 d . . .
H6A H 0.7173 1.1459 0.0827 0.076 Uiso 1 1 calc R . .
H6B H 0.8697 1.1415 0.1095 0.076 Uiso 1 1 calc R . .
C7 C 0.8712(6) 1.0461(3) 0.05703(13) 0.0781(11) Uani 1 1 d . . .
H7A H 0.7943 1.0103 0.0399 0.094 Uiso 1 1 calc R . .
H7B H 0.9402 0.9938 0.0686 0.094 Uiso 1 1 calc R . .
C8 C 0.9610(4) 1.1188(3) 0.02699(12) 0.0695(10) Uani 1 1 d . . .
C9 C 0.9435(6) 1.2705(4) -0.01830(16) 0.0897(14) Uani 1 1 d . . .
H9A H 1.0145 1.3149 -0.0033 0.135 Uiso 1 1 calc R . .
H9B H 0.8645 1.3122 -0.0312 0.135 Uiso 1 1 calc R . .
H9C H 0.9959 1.2325 -0.0408 0.135 Uiso 1 1 calc R . .
C10 C 1.2101(3) 0.7508(2) 0.24047(10) 0.0489(7) Uani 1 1 d . . .
H10 H 1.2778 0.7024 0.2521 0.059 Uiso 1 1 calc R . .
C11 C 1.1881(3) 0.7609(2) 0.19586(10) 0.0481(7) Uani 1 1 d . . .
C12 C 1.0875(3) 0.8321(2) 0.17754(9) 0.0431(6) Uani 1 1 d . . .
H12A H 1.0773 0.8371 0.1474 0.052 Uiso 1 1 calc R . .
C13 C 0.5903(3) 0.9571(2) 0.10831(9) 0.0458(6) Uani 1 1 d . . .
C14 C 0.3548(4) 0.9620(4) 0.07062(15) 0.0801(12) Uani 1 1 d . . .
H14A H 0.3833 0.9183 0.0465 0.120 Uiso 1 1 calc R . .
H14B H 0.2818 1.0128 0.0609 0.120 Uiso 1 1 calc R . .
H14C H 0.3102 0.9201 0.0933 0.120 Uiso 1 1 calc R . .
C15 C 0.5930(3) 0.8354(2) 0.25520(9) 0.0407(6) Uani 1 1 d . . .
C16 C 0.6448(3) 0.7873(2) 0.21719(8) 0.0379(5) Uani 1 1 d . . .
H16 H 0.6173 0.8132 0.1899 0.045 Uiso 1 1 calc R . .
C17 C 0.7381(3) 0.70008(19) 0.22043(8) 0.0343(5) Uani 1 1 d . . .
C18 C 0.8063(3) 0.6438(2) 0.18108(8) 0.0375(5) Uani 1 1 d . . .
C19 C 0.8091(3) 0.6258(2) 0.10091(8) 0.0458(6) Uani 1 1 d . . .
H19 H 0.8665 0.5625 0.1080 0.055 Uiso 1 1 calc R . .
C20 C 0.6685(4) 0.5958(3) 0.07288(9) 0.0562(8) Uani 1 1 d . . .
H20A H 0.6073 0.6575 0.0677 0.067 Uiso 1 1 calc R . .
H20B H 0.7031 0.5699 0.0448 0.067 Uiso 1 1 calc R . .
C21 C 0.5699(4) 0.5132(3) 0.09470(10) 0.0601(8) Uani 1 1 d . . .
H21A H 0.6207 0.4462 0.0928 0.072 Uiso 1 1 calc R . .
H21B H 0.5579 0.5302 0.1254 0.072 Uiso 1 1 calc R . .
C22 C 0.4155(4) 0.5056(3) 0.07384(11) 0.0602(8) Uani 1 1 d . . .
C23 C 0.1749(5) 0.4218(5) 0.0784(2) 0.1134(19) Uani 1 1 d . . .
H23A H 0.1373 0.4876 0.0680 0.170 Uiso 1 1 calc R . .
H23B H 0.1108 0.3974 0.1017 0.170 Uiso 1 1 calc R . .
H23C H 0.1740 0.3721 0.0549 0.170 Uiso 1 1 calc R . .
C24 C 0.7753(3) 0.6603(2) 0.26170(8) 0.0366(5) Uani 1 1 d . . .
H24 H 0.8380 0.6022 0.2644 0.044 Uiso 1 1 calc R . .
C25 C 0.7163(3) 0.7095(2) 0.29856(8) 0.0403(6) Uani 1 1 d . . .
C26 C 0.6258(3) 0.7984(2) 0.29675(9) 0.0435(6) Uani 1 1 d . . .
H26 H 0.5895 0.8311 0.3218 0.052 Uiso 1 1 calc R . .
C27 C 0.9123(3) 0.6997(2) 0.07562(9) 0.0469(6) Uani 1 1 d . . .
C28 C 1.0806(5) 0.7163(4) 0.01563(13) 0.0824(12) Uani 1 1 d . . .
H28A H 1.0249 0.7748 0.0043 0.124 Uiso 1 1 calc R . .
H28B H 1.1199 0.6757 -0.0082 0.124 Uiso 1 1 calc R . .
H28C H 1.1637 0.7406 0.0333 0.124 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 N1 1.221(4) . ?
N3 C4 1.358(4) . ?
N3 C5 1.457(3) . ?
N3 H3 0.8600 . ?
O7 C8 1.328(5) . ?
O7 C9 1.462(5) . ?
O3 N1 1.218(4) . ?
O2 N2 1.208(4) . ?
O4 N2 1.209(5) . ?
O8 C13 1.210(4) . ?
O6 C8 1.194(5) . ?
O5 C4 1.227(4) . ?
O10 N4 1.219(4) . ?
O11 C22 1.342(4) . ?
O11 C23 1.443(6) . ?
O12 C22 1.203(4) . ?
O13 C18 1.216(3) . ?
O14 N6 1.207(4) . ?
O15 N6 1.207(4) . ?
O16 N4 1.221(4) . ?
O17 C27 1.329(3) . ?
O17 C28 1.463(4) . ?
O18 C27 1.207(4) . ?
N1 C1 1.493(4) . ?
N2 C11 1.480(4) . ?
O9 C13 1.316(3) . ?
O9 C14 1.456(5) . ?
N4 C15 1.488(4) . ?
N5 C18 1.345(3) . ?
N5 C19 1.460(3) . ?
N5 H5 0.8600 . ?
N6 C25 1.494(4) . ?
C1 C10 1.384(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9300 . ?
C3 C12 1.397(4) . ?
C3 C4 1.506(4) . ?
C5 C13 1.532(4) . ?
C5 C6 1.536(5) . ?
C5 H5A 0.9800 . ?
C6 C7 1.483(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.527(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C12 H12A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C26 1.387(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9300 . ?
C17 C24 1.400(3) . ?
C17 C18 1.526(3) . ?
C19 C27 1.522(4) . ?
C19 C20 1.550(4) . ?
C19 H19 0.9800 . ?
C20 C21 1.521(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.499(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.392(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(4) . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
C4 N3 C5 122.4(2) . . ?
C4 N3 H3 118.8 . . ?
C5 N3 H3 118.8 . . ?
C8 O7 C9 118.2(3) . . ?
C22 O11 C23 116.6(4) . . ?
C27 O17 C28 115.7(3) . . ?
O3 N1 O1 124.9(3) . . ?
O3 N1 C1 117.2(3) . . ?
O1 N1 C1 118.0(3) . . ?
O2 N2 O4 123.5(4) . . ?
O2 N2 C11 117.5(3) . . ?
O4 N2 C11 119.0(3) . . ?
C13 O9 C14 117.0(3) . . ?
O10 N4 O16 124.3(3) . . ?
O10 N4 C15 118.0(3) . . ?
O16 N4 C15 117.7(3) . . ?
C18 N5 C19 122.8(2) . . ?
C18 N5 H5 118.6 . . ?
C19 N5 H5 118.6 . . ?
O14 N6 O15 123.5(3) . . ?
O14 N6 C25 118.5(3) . . ?
O15 N6 C25 118.0(2) . . ?
C10 C1 C2 123.6(3) . . ?
C10 C1 N1 117.2(3) . . ?
C2 C1 N1 119.2(3) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C12 C3 C2 119.5(2) . . ?
C12 C3 C4 122.8(2) . . ?
C2 C3 C4 117.7(2) . . ?
O5 C4 N3 123.5(3) . . ?
O5 C4 C3 120.6(2) . . ?
N3 C4 C3 115.9(2) . . ?
N3 C5 C13 108.9(2) . . ?
N3 C5 C6 112.3(3) . . ?
C13 C5 C6 115.6(3) . . ?
N3 C5 H5A 106.5 . . ?
C13 C5 H5A 106.5 . . ?
C6 C5 H5A 106.5 . . ?
C7 C6 C5 113.2(3) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 114.3(3) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O6 C8 O7 122.0(4) . . ?
O6 C8 C7 126.0(4) . . ?
O7 C8 C7 111.8(3) . . ?
O7 C9 H9A 109.5 . . ?
O7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 C11 116.0(3) . . ?
C1 C10 H10 122.0 . . ?
C11 C10 H10 122.0 . . ?
C10 C11 C12 123.2(3) . . ?
C10 C11 N2 118.9(3) . . ?
C12 C11 N2 117.8(3) . . ?
C11 C12 C3 119.1(3) . . ?
C11 C12 H12A 120.5 . . ?
C3 C12 H12A 120.5 . . ?
O8 C13 O9 123.6(3) . . ?
O8 C13 C5 125.1(3) . . ?
O9 C13 C5 111.3(2) . . ?
O9 C14 H14A 109.5 . . ?
O9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26 C15 C16 123.1(2) . . ?
C26 C15 N4 118.8(2) . . ?
C16 C15 N4 118.1(2) . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C24 119.6(2) . . ?
C16 C17 C18 123.7(2) . . ?
C24 C17 C18 116.6(2) . . ?
O13 C18 N5 122.7(2) . . ?
O13 C18 C17 120.6(2) . . ?
N5 C18 C17 116.7(2) . . ?
N5 C19 C27 110.2(2) . . ?
N5 C19 C20 109.5(2) . . ?
C27 C19 C20 110.2(2) . . ?
N5 C19 H19 109.0 . . ?
C27 C19 H19 109.0 . . ?
C20 C19 H19 109.0 . . ?
C21 C20 C19 112.4(2) . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 111.8(3) . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
O12 C22 O11 123.2(4) . . ?
O12 C22 C21 125.9(3) . . ?
O11 C22 C21 110.9(3) . . ?
O11 C23 H23A 109.5 . . ?
O11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C17 118.6(2) . . ?
C25 C24 H24 120.7 . . ?
C17 C24 H24 120.7 . . ?
C26 C25 C24 123.5(2) . . ?
C26 C25 N6 118.1(2) . . ?
C24 C25 N6 118.4(2) . . ?
C15 C26 C25 115.8(2) . . ?
C15 C26 H26 122.1 . . ?
C25 C26 H26 122.1 . . ?
O18 C27 O17 123.4(3) . . ?
O18 C27 C19 125.2(3) . . ?
O17 C27 C19 111.3(3) . . ?
O17 C28 H28A 109.5 . . ?
O17 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O17 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.15
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
