# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cd16308
_database_code_depnum_ccdc_archive 'CCDC 1495666'
_audit_update_record             
;
2016-07-24 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H2 N10 O8'
_chemical_formula_weight         342.18

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   24.929(3)
_cell_length_b                   24.929(3)
_cell_length_c                   5.2298(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2814.7(9)
_cell_formula_units_Z            9
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1658
_cell_measurement_theta_min      5.659
_cell_measurement_theta_max      49.922

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             1548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.168
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6137
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5145
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.830
_diffrn_reflns_theta_max         24.958
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             1091
_reflns_number_gt                997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+2.6163P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1091
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.085 90 27 ' '
2 0.333 0.667 0.075 89 27 ' '
3 0.667 0.333 -0.120 89 27 ' '
_platon_squeeze_details          
;
;


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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.87459(8) 0.30077(7) 0.9359(3) 0.0414(5) Uani 1 1 d . . . . .
N2 N 0.97222(8) 0.38356(7) 0.9607(3) 0.0411(5) Uani 1 1 d . . . . .
N3 N 0.94470(7) 0.44961(7) 0.4208(3) 0.0346(4) Uani 1 1 d . . . . .
N4 N 0.84104(7) 0.33268(8) 0.5688(4) 0.0402(5) Uani 1 1 d . . . . .
N5 N 0.78444(8) 0.28114(7) 0.5420(4) 0.0416(5) Uani 1 1 d . . . . .
O1 O 0.93094(7) 0.32814(6) 1.0649(3) 0.0466(4) Uani 1 1 d . . . . .
O2 O 0.97379(6) 0.50680(6) 0.2815(3) 0.0467(4) Uani 1 1 d . . . . .
O3 O 0.76774(8) 0.24159(7) 0.7026(3) 0.0598(5) Uani 1 1 d . . . . .
O4 O 0.75638(7) 0.27970(7) 0.3502(4) 0.0604(5) Uani 1 1 d . . . . .
C1 C 0.88269(8) 0.33966(8) 0.7542(3) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.94374(8) 0.39199(8) 0.7719(3) 0.0302(4) Uani 1 1 d . . . . .
C3 C 0.97255(8) 0.44849(8) 0.6195(3) 0.0298(4) Uani 1 1 d . . . . .
H4 H 0.8463(10) 0.3599(10) 0.471(5) 0.041(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.299(2) . ?
N1 O1 1.391(2) . ?
N2 C2 1.293(2) . ?
N2 O1 1.357(2) . ?
N3 C3 1.258(2) . ?
N3 O2 1.434(2) . ?
N4 N5 1.360(2) . ?
N4 C1 1.367(3) . ?
N4 H4 0.81(2) . ?
N5 O3 1.200(2) . ?
N5 O4 1.213(2) . ?
O2 C3 1.345(2) 10_766 ?
C1 C2 1.429(3) . ?
C2 C3 1.457(2) . ?
C3 O2 1.345(2) 10_766 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 O1 104.28(14) . . ?
C2 N2 O1 105.87(15) . . ?
C3 N3 O2 115.58(14) . . ?
N5 N4 C1 123.83(17) . . ?
N5 N4 H4 112.7(16) . . ?
C1 N4 H4 123.3(16) . . ?
O3 N5 O4 126.60(18) . . ?
O3 N5 N4 118.31(19) . . ?
O4 N5 N4 115.07(18) . . ?
N2 O1 N1 111.73(14) . . ?
C3 O2 N3 115.29(13) 10_766 . ?
N1 C1 N4 126.82(17) . . ?
N1 C1 C2 109.33(16) . . ?
N4 C1 C2 123.84(16) . . ?
N2 C2 C1 108.78(16) . . ?
N2 C2 C3 121.97(16) . . ?
C1 C2 C3 129.21(17) . . ?
N3 C3 O2 129.13(16) . 10_766 ?
N3 C3 C2 117.56(16) . . ?
O2 C3 C2 113.30(15) 10_766 . ?

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
C1 N4 N5 O3 6.6(3) . . . . ?
C1 N4 N5 O4 -171.73(18) . . . . ?
C2 N2 O1 N1 0.2(2) . . . . ?
C1 N1 O1 N2 0.6(2) . . . . ?
C3 N3 O2 C3 0.7(3) . . . 10_766 ?
O1 N1 C1 N4 177.66(17) . . . . ?
O1 N1 C1 C2 -1.06(19) . . . . ?
N5 N4 C1 N1 -3.0(3) . . . . ?
N5 N4 C1 C2 175.57(17) . . . . ?
O1 N2 C2 C1 -0.85(19) . . . . ?
O1 N2 C2 C3 177.03(15) . . . . ?
N1 C1 C2 N2 1.3(2) . . . . ?
N4 C1 C2 N2 -177.50(17) . . . . ?
N1 C1 C2 C3 -176.40(17) . . . . ?
N4 C1 C2 C3 4.8(3) . . . . ?
O2 N3 C3 O2 -0.8(3) . . . 10_766 ?
O2 N3 C3 C2 178.11(14) . . . . ?
N2 C2 C3 N3 171.31(17) . . . . ?
C1 C2 C3 N3 -11.3(3) . . . . ?
N2 C2 C3 O2 -9.6(2) . . . 10_766 ?
C1 C2 C3 O2 167.81(17) . . . 10_766 ?

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
N4 H4 O4 0.81(2) 2.32(2) 3.026(2) 147(2) 18_545
N4 H4 N3 0.81(2) 2.37(2) 2.871(2) 121.5(19) .
N4 H4 O4 0.81(2) 2.32(2) 3.026(2) 147(2) 18_545
N4 H4 N3 0.81(2) 2.37(2) 2.871(2) 121.5(19) .
N4 H4 O4 0.81(2) 2.32(2) 3.026(2) 147(2) 18_545
N4 H4 N3 0.81(2) 2.37(2) 2.871(2) 121.5(19) .
N4 H4 N3 0.81(2) 2.37(2) 2.871(2) 121.5(19) .
N4 H4 O4 0.81(2) 2.32(2) 3.026(2) 147(2) 18_545
N4 H4 N3 0.81(2) 2.37(2) 2.871(2) 121.5(19) .
N4 H4 O4 0.81(2) 2.32(2) 3.026(2) 147(2) 18_545
N4 H4 N3 0.81(2) 2.37(2) 2.871(2) 121.5(19) .
N4 H4 O4 0.81(2) 2.32(2) 3.026(2) 147(2) 18_545
N4 H4 N3 0.81(2) 2.37(2) 2.871(2) 121.5(19) .
N4 H4 O4 0.81(2) 2.32(2) 3.026(2) 147(2) 18_545

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16348
_database_code_depnum_ccdc_archive 'CCDC 1495667'
_audit_update_record             
;
2016-07-24 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H10 N12 O9'
_chemical_formula_weight         394.26

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.327(3)
_cell_length_b                   8.515(3)
_cell_length_c                   10.354(3)
_cell_angle_alpha                85.243(7)
_cell_angle_beta                 83.980(7)
_cell_angle_gamma                85.302(7)
_cell_volume                     725.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    793
_cell_measurement_theta_min      6.005
_cell_measurement_theta_max      47.408

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4026
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.983
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2552
_reflns_number_gt                1730
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1509P)²+0.1122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2552
_refine_ls_number_parameters     284
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2357
_refine_ls_wR_factor_gt          0.2047
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1298(4) 0.6159(4) 0.8267(4) 0.0492(10) Uani 1 1 d . . . . .
N2 N 0.3729(4) 0.6940(4) 0.9685(3) 0.0420(8) Uani 1 1 d . . . . .
N3 N 0.0284(4) 0.8800(4) 1.1336(3) 0.0418(9) Uani 1 1 d . . . . .
N4 N 0.1797(4) 1.0079(4) 1.2545(3) 0.0423(9) Uani 1 1 d . . . . .
N5 N 0.4437(4) 0.9139(3) 1.1518(3) 0.0352(8) Uani 1 1 d . . . . .
N6 N 0.5223(4) 0.9922(3) 1.2244(3) 0.0357(8) Uani 1 1 d . . . . .
N7 N 0.4731(4) 0.4207(4) 0.6682(3) 0.0389(8) Uani 1 1 d . . . . .
N8 N 0.3212(4) 0.2953(4) 0.5457(3) 0.0402(8) Uani 1 1 d . . . . .
N9 N 0.0578(4) 0.4018(3) 0.6409(3) 0.0343(8) Uani 1 1 d . . . . .
N10 N -0.0221(4) 0.3199(3) 0.5711(3) 0.0323(7) Uani 1 1 d . . . . .
N11 N 0.2259(5) 0.3801(5) 0.2466(4) 0.0432(9) Uani 1 1 d D . . . .
N12 N 0.7478(5) 0.0663(4) 0.4561(4) 0.0421(9) Uani 1 1 d D . . . .
O1 O 0.4041(3) 0.5958(4) 0.8628(3) 0.0709(11) Uani 1 1 d . U . . .
O2 O 0.1034(4) 0.7219(6) 0.9277(5) 0.1091(17) Uani 1 1 d . U . . .
O3 O 0.0246(3) 0.9763(3) 1.2313(3) 0.0489(8) Uani 1 1 d . . . . .
O4 O 0.6724(3) 0.9800(3) 1.2047(3) 0.0502(8) Uani 1 1 d . . . . .
O5 O 0.4557(3) 1.0771(3) 1.3114(3) 0.0497(8) Uani 1 1 d . . . . .
O6 O 0.4767(3) 0.3199(3) 0.5728(3) 0.0454(8) Uani 1 1 d . . . . .
O7 O 0.0429(3) 0.2254(3) 0.4903(3) 0.0413(7) Uani 1 1 d . . . . .
O8 O -0.1729(3) 0.3383(3) 0.5878(3) 0.0444(7) Uani 1 1 d . . . . .
O9 O 0.2731(5) 0.2738(4) 0.9923(3) 0.0555(9) Uani 1 1 d D . . . .
C1 C 0.2760(4) 0.5655(4) 0.8034(4) 0.0386(10) Uani 1 1 d . . . . .
C2 C 0.3225(4) 0.4586(4) 0.6998(3) 0.0318(9) Uani 1 1 d . . . . .
C3 C 0.2236(4) 0.3801(4) 0.6238(3) 0.0312(8) Uani 1 1 d . . . . .
C4 C 0.2283(5) 0.7446(4) 0.9920(4) 0.0376(9) Uani 1 1 d . . . . .
C5 C 0.1799(4) 0.8481(4) 1.0975(3) 0.0319(9) Uani 1 1 d . . . . .
C6 C 0.2781(4) 0.9272(4) 1.1721(3) 0.0332(9) Uani 1 1 d . . . . .
H1 H 0.303(6) 0.438(7) 0.246(7) 0.11(3) Uiso 1 1 d D . . . .
H2 H 0.259(10) 0.312(7) 0.301(6) 0.16(3) Uiso 1 1 d D . . . .
H3 H 0.236(5) 0.356(5) 0.169(2) 0.052(13) Uiso 1 1 d D . . . .
H4 H 0.133(3) 0.419(5) 0.263(5) 0.062(15) Uiso 1 1 d D . . . .
H5 H 0.817(6) 0.131(5) 0.461(6) 0.09(2) Uiso 1 1 d D . . . .
H6 H 0.800(9) -0.016(6) 0.485(8) 0.17(4) Uiso 1 1 d D . . . .
H7 H 0.666(8) 0.045(11) 0.507(8) 0.19(4) Uiso 1 1 d D . . . .
H8 H 0.687(8) 0.064(9) 0.397(5) 0.13(3) Uiso 1 1 d D . . . .
H9A H 0.368(3) 0.247(7) 0.971(6) 0.11(2) Uiso 1 1 d D . . . .
H9B H 0.206(8) 0.253(10) 0.946(7) 0.16(4) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.262(5) . ?
N1 O2 1.425(4) . ?
N2 C4 1.252(5) . ?
N2 O1 1.422(4) . ?
N3 C5 1.291(5) . ?
N3 O3 1.350(4) . ?
N4 C6 1.316(5) . ?
N4 O3 1.390(4) . ?
N5 N6 1.302(4) . ?
N5 C6 1.370(5) . ?
N6 O4 1.242(4) . ?
N6 O5 1.257(4) . ?
N7 C2 1.284(4) . ?
N7 O6 1.358(4) . ?
N8 C3 1.303(5) . ?
N8 O6 1.389(4) . ?
N9 N10 1.309(4) . ?
N9 C3 1.372(5) . ?
N10 O8 1.248(4) . ?
N10 O7 1.259(4) . ?
N11 H1 0.84(2) . ?
N11 H2 0.82(2) . ?
N11 H3 0.84(2) . ?
N11 H4 0.823(19) . ?
N12 H5 0.83(2) . ?
N12 H6 0.84(2) . ?
N12 H7 0.84(2) . ?
N12 H8 0.83(2) . ?
O1 C1 1.338(5) . ?
O2 C4 1.328(5) . ?
O9 H9A 0.81(2) . ?
O9 H9B 0.81(2) . ?
C1 C2 1.465(5) . ?
C2 C3 1.435(5) . ?
C4 C5 1.463(5) . ?
C5 C6 1.424(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 O2 113.8(3) . . ?
C4 N2 O1 115.2(3) . . ?
C5 N3 O3 105.6(3) . . ?
C6 N4 O3 105.4(3) . . ?
N6 N5 C6 117.1(3) . . ?
O4 N6 O5 119.3(3) . . ?
O4 N6 N5 116.6(3) . . ?
O5 N6 N5 124.2(3) . . ?
C2 N7 O6 105.6(3) . . ?
C3 N8 O6 105.9(3) . . ?
N10 N9 C3 116.5(3) . . ?
O8 N10 O7 119.1(3) . . ?
O8 N10 N9 116.5(3) . . ?
O7 N10 N9 124.5(3) . . ?
H1 N11 H2 95(7) . . ?
H1 N11 H3 101(5) . . ?
H2 N11 H3 116(6) . . ?
H1 N11 H4 118(6) . . ?
H2 N11 H4 116(7) . . ?
H3 N11 H4 108(5) . . ?
H5 N12 H6 98(6) . . ?
H5 N12 H7 130(8) . . ?
H6 N12 H7 91(7) . . ?
H5 N12 H8 127(7) . . ?
H6 N12 H8 122(7) . . ?
H7 N12 H8 86(7) . . ?
C1 O1 N2 116.6(3) . . ?
C4 O2 N1 117.7(3) . . ?
N3 O3 N4 111.4(3) . . ?
N7 O6 N8 111.1(2) . . ?
H9A O9 H9B 118(8) . . ?
N1 C1 O1 128.5(4) . . ?
N1 C1 C2 120.0(3) . . ?
O1 C1 C2 111.4(3) . . ?
N7 C2 C3 110.4(3) . . ?
N7 C2 C1 119.5(3) . . ?
C3 C2 C1 130.1(3) . . ?
N8 C3 N9 131.9(4) . . ?
N8 C3 C2 107.1(3) . . ?
N9 C3 C2 121.0(3) . . ?
N2 C4 O2 127.9(4) . . ?
N2 C4 C5 120.8(3) . . ?
O2 C4 C5 111.3(3) . . ?
N3 C5 C6 110.5(3) . . ?
N3 C5 C4 120.1(3) . . ?
C6 C5 C4 129.4(3) . . ?
N4 C6 N5 130.9(4) . . ?
N4 C6 C5 107.1(3) . . ?
N5 C6 C5 122.0(3) . . ?

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
C6 N5 N6 O4 -179.6(3) . . . . ?
C6 N5 N6 O5 0.6(5) . . . . ?
C3 N9 N10 O8 179.2(3) . . . . ?
C3 N9 N10 O7 -0.5(5) . . . . ?
C4 N2 O1 C1 -1.7(6) . . . . ?
C1 N1 O2 C4 -5.7(7) . . . . ?
C5 N3 O3 N4 1.3(4) . . . . ?
C6 N4 O3 N3 -1.3(4) . . . . ?
C2 N7 O6 N8 -0.2(4) . . . . ?
C3 N8 O6 N7 0.0(4) . . . . ?
O2 N1 C1 O1 1.9(7) . . . . ?
O2 N1 C1 C2 -178.5(4) . . . . ?
N2 O1 C1 N1 1.8(7) . . . . ?
N2 O1 C1 C2 -177.8(3) . . . . ?
O6 N7 C2 C3 0.3(4) . . . . ?
O6 N7 C2 C1 179.0(3) . . . . ?
N1 C1 C2 N7 173.1(4) . . . . ?
O1 C1 C2 N7 -7.2(5) . . . . ?
N1 C1 C2 C3 -8.6(6) . . . . ?
O1 C1 C2 C3 171.1(4) . . . . ?
O6 N8 C3 N9 -179.8(3) . . . . ?
O6 N8 C3 C2 0.2(4) . . . . ?
N10 N9 C3 N8 2.9(6) . . . . ?
N10 N9 C3 C2 -177.1(3) . . . . ?
N7 C2 C3 N8 -0.3(4) . . . . ?
C1 C2 C3 N8 -178.8(4) . . . . ?
N7 C2 C3 N9 179.7(3) . . . . ?
C1 C2 C3 N9 1.2(6) . . . . ?
O1 N2 C4 O2 -2.5(7) . . . . ?
O1 N2 C4 C5 -179.5(3) . . . . ?
N1 O2 C4 N2 6.5(8) . . . . ?
N1 O2 C4 C5 -176.4(4) . . . . ?
O3 N3 C5 C6 -0.8(4) . . . . ?
O3 N3 C5 C4 179.9(3) . . . . ?
N2 C4 C5 N3 -169.5(4) . . . . ?
O2 C4 C5 N3 13.1(5) . . . . ?
N2 C4 C5 C6 11.4(6) . . . . ?
O2 C4 C5 C6 -166.0(4) . . . . ?
O3 N4 C6 N5 -179.9(3) . . . . ?
O3 N4 C6 C5 0.7(4) . . . . ?
N6 N5 C6 N4 0.0(6) . . . . ?
N6 N5 C6 C5 179.4(3) . . . . ?
N3 C5 C6 N4 0.1(4) . . . . ?
C4 C5 C6 N4 179.3(3) . . . . ?
N3 C5 C6 N5 -179.4(3) . . . . ?
C4 C5 C6 N5 -0.2(6) . . . . ?

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
O9 H9B N3 0.81(2) 2.57(3) 3.350(5) 160(8) 2_567
O9 H9A N5 0.81(2) 2.34(4) 3.063(5) 148(6) 2_667
O9 H9A N2 0.81(2) 2.41(5) 3.055(5) 137(6) 2_667
N12 H8 O5 0.83(2) 2.20(4) 2.978(5) 156(7) 1_544
N12 H8 O4 0.83(2) 2.19(5) 2.906(5) 144(7) 1_544
N12 H8 N6 0.83(2) 2.51(3) 3.327(5) 167(7) 1_544
N12 H7 O5 0.84(2) 2.25(5) 3.026(5) 153(9) 2_667
N12 H6 O7 0.84(2) 2.14(3) 2.964(5) 166(9) 2_656
N12 H5 O8 0.83(2) 2.30(5) 2.936(5) 133(5) 1_655
N12 H5 O7 0.83(2) 2.17(3) 2.968(5) 161(6) 1_655
N12 H5 N10 0.83(2) 2.59(3) 3.367(5) 157(6) 1_655
N11 H4 N9 0.823(19) 2.31(3) 3.074(5) 154(5) 2_566
N11 H4 N1 0.823(19) 2.52(4) 3.131(5) 132(4) 2_566
N11 H3 O9 0.84(2) 2.00(2) 2.833(5) 173(4) 1_554
N11 H2 O7 0.82(2) 2.62(8) 3.066(5) 115(7) .
N11 H2 O5 0.82(2) 2.48(6) 3.153(5) 139(7) 1_544
N11 H2 N8 0.82(2) 2.63(6) 3.286(5) 137(7) .
N11 H1 O1 0.84(2) 2.58(5) 3.186(5) 130(6) 2_666
N11 H1 N7 0.84(2) 2.57(3) 3.368(5) 160(6) 2_666

_refine_diff_density_max         0.761
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.135

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dm16351_0m
_database_code_depnum_ccdc_archive 'CCDC 1495668'
_audit_update_record             
;
2016-07-24 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;
_audit_creation_date             2016-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 N10 O8, 2(H4 N O)'
_chemical_formula_sum            'C6 H8 N12 O10'
_chemical_formula_weight         408.24
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4121(19)
_cell_length_b                   4.1853(7)
_cell_length_c                   14.866(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.460(3)
_cell_angle_gamma                90
_cell_volume                     708.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1570
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.78
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0467 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.9148.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6729
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.617
_diffrn_reflns_theta_min         1.789
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1674
_reflns_number_total             2164
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.1960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.029
;
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.03782(11) 0.3010(4) 0.05369(8) 0.0377(4) Uani 1 1 d . . . . .
O2 O 0.15058(9) 0.2149(2) 0.33737(7) 0.0194(2) Uani 1 1 d . . . . .
O3 O 0.41530(9) 0.8254(3) 0.40587(7) 0.0235(2) Uani 1 1 d . . . . .
O4 O 0.44176(8) 1.1080(2) 0.29271(7) 0.0165(2) Uani 1 1 d . . . . .
N1 N 0.10792(10) 0.6530(3) 0.04841(9) 0.0183(3) Uani 1 1 d . . . . .
N2 N 0.08034(10) 0.2033(3) 0.23976(9) 0.0175(2) Uani 1 1 d . . . . .
N3 N 0.24287(10) 0.4338(3) 0.35670(9) 0.0173(3) Uani 1 1 d . . . . .
N4 N 0.29421(10) 0.7714(3) 0.24468(8) 0.0144(2) Uani 1 1 d . . . . .
N5 N 0.38473(10) 0.8957(3) 0.31834(8) 0.0144(2) Uani 1 1 d . . . . .
C1 C 0.06454(11) 0.4638(3) 0.09243(10) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.12515(11) 0.4063(3) 0.19761(10) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.22883(11) 0.5517(3) 0.27042(10) 0.0138(3) Uani 1 1 d . . . . .
O5 O 0.34504(10) 1.1954(2) 0.09900(8) 0.0208(2) Uani 1 1 d . . . . .
H5 H 0.376(2) 1.173(6) 0.1677(18) 0.049(6) Uiso 1 1 d . . . . .
N6 N 0.34811(11) 0.8831(3) 0.06328(9) 0.0151(2) Uani 1 1 d . . . . .
H6A H 0.2910(17) 0.765(5) 0.0687(14) 0.028(5) Uiso 1 1 d . . . . .
H6B H 0.4177(18) 0.788(5) 0.0979(15) 0.028(5) Uiso 1 1 d . . . . .
H6C H 0.3336(18) 0.911(5) -0.0009(16) 0.035(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4306(16) 3_565 ?
O1 C1 1.3520(17) . ?
O2 N2 1.3641(15) . ?
O2 N3 1.4044(15) . ?
O3 N5 1.2372(15) . ?
O4 N5 1.2847(15) . ?
N1 O1 1.4306(16) 3_565 ?
N1 C1 1.2750(18) . ?
N2 C2 1.3042(17) . ?
N3 C3 1.3196(18) . ?
N4 N5 1.3238(15) . ?
N4 C3 1.3776(17) . ?
C1 C2 1.4603(19) . ?
C2 C3 1.4454(18) . ?
O5 H5 0.94(2) . ?
O5 N6 1.4168(16) . ?
N6 H6A 0.89(2) . ?
N6 H6B 0.90(2) . ?
N6 H6C 0.91(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 N1 117.09(11) . 3_565 ?
N2 O2 N3 111.39(10) . . ?
C1 N1 O1 115.18(11) . 3_565 ?
C2 N2 O2 105.89(11) . . ?
C3 N3 O2 105.29(11) . . ?
N5 N4 C3 115.62(11) . . ?
O3 N5 O4 120.12(11) . . ?
O3 N5 N4 125.49(12) . . ?
O4 N5 N4 114.38(11) . . ?
O1 C1 C2 111.66(12) . . ?
N1 C1 O1 127.71(13) . . ?
N1 C1 C2 120.62(12) . . ?
N2 C2 C1 119.04(12) . . ?
N2 C2 C3 109.72(12) . . ?
C3 C2 C1 131.14(12) . . ?
N3 C3 N4 130.93(12) . . ?
N3 C3 C2 107.71(12) . . ?
N4 C3 C2 121.36(12) . . ?
N6 O5 H5 104.8(14) . . ?
O5 N6 H6A 109.6(12) . . ?
O5 N6 H6B 110.8(12) . . ?
O5 N6 H6C 104.8(13) . . ?
H6A N6 H6B 108.5(17) . . ?
H6A N6 H6C 109.4(18) . . ?
H6B N6 H6C 113.6(18) . . ?

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
O5 H5 O4 0.94(2) 1.73(2) 2.6674(15) 174(2) .
N6 H6B O4 0.90(2) 2.00(2) 2.8750(16) 163.0(17) 2_645

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
O1 N1 C1 O1 1.1(3) 3_565 . . . ?
O1 N1 C1 C2 -177.57(13) 3_565 . . . ?
O1 C1 C2 N2 3.43(18) . . . . ?
O1 C1 C2 C3 -172.57(14) . . . . ?
O2 N2 C2 C1 -176.14(11) . . . . ?
O2 N2 C2 C3 0.66(14) . . . . ?
O2 N3 C3 N4 -178.84(13) . . . . ?
O2 N3 C3 C2 0.99(14) . . . . ?
N1 O1 C1 N1 -1.1(3) 3_565 . . . ?
N1 O1 C1 C2 177.65(12) 3_565 . . . ?
N1 C1 C2 N2 -177.75(13) . . . . ?
N1 C1 C2 C3 6.3(2) . . . . ?
N2 O2 N3 C3 -0.63(14) . . . . ?
N2 C2 C3 N3 -1.09(16) . . . . ?
N2 C2 C3 N4 178.76(12) . . . . ?
N3 O2 N2 C2 -0.04(14) . . . . ?
N5 N4 C3 N3 -2.5(2) . . . . ?
N5 N4 C3 C2 177.72(12) . . . . ?
C1 C2 C3 N3 175.19(13) . . . . ?
C1 C2 C3 N4 -5.0(2) . . . . ?
C3 N4 N5 O3 1.58(19) . . . . ?
C3 N4 N5 O4 -177.68(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cd16345
_database_code_depnum_ccdc_archive 'CCDC 1495669'
_audit_update_record             
;
2016-07-24 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N18 O8'
_chemical_formula_weight         510.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   8.248(2)
_cell_length_b                   16.509(4)
_cell_length_c                   7.2536(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.398(5)
_cell_angle_gamma                90
_cell_volume                     979.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1355
_cell_measurement_theta_min      4.980
_cell_measurement_theta_max      46.599

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6063
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5442
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.467
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1821
_reflns_number_gt                1449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.1388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1821
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H7 H -0.216(3) 0.6092(17) -0.128(4) 0.073(9) Uiso 1 1 d . . . . .
N1 N 0.90746(19) 0.43251(11) 0.5378(2) 0.0381(4) Uani 1 1 d . . . . .
N2 N 0.6142(2) 0.54797(11) 0.2557(3) 0.0435(5) Uani 1 1 d . . . . .
N3 N 0.4247(2) 0.44612(11) 0.2499(3) 0.0405(5) Uani 1 1 d . . . . .
N4 N 0.6059(2) 0.34688(10) 0.4233(2) 0.0360(4) Uani 1 1 d . . . . .
N5 N 0.4851(2) 0.29267(11) 0.4242(3) 0.0421(5) Uani 1 1 d . . . . .
N6 N 0.0219(2) 0.58500(12) -0.1024(3) 0.0457(5) Uani 1 1 d . . . . .
N7 N -0.1183(2) 0.62240(12) -0.0724(3) 0.0435(5) Uani 1 1 d . . . . .
N8 N 0.06436(19) 0.67714(10) 0.1155(2) 0.0306(4) Uani 1 1 d . . . . .
N9 N 0.1418(2) 0.72818(13) 0.2564(3) 0.0432(5) Uani 1 1 d . . . . .
O1 O 1.07551(18) 0.44259(10) 0.6128(3) 0.0601(5) Uani 1 1 d . . . . .
O2 O 0.45668(17) 0.52563(10) 0.1946(2) 0.0500(5) Uani 1 1 d . . . . .
O3 O 0.5264(2) 0.22519(10) 0.4909(3) 0.0593(5) Uani 1 1 d . . . . .
O4 O 0.34085(19) 0.30812(11) 0.3632(3) 0.0612(5) Uani 1 1 d . . . . .
C1 C 0.8488(2) 0.48990(12) 0.4336(3) 0.0312(5) Uani 1 1 d . . . . .
C2 C 0.6795(2) 0.48573(12) 0.3467(3) 0.0308(5) Uani 1 1 d . . . . .
C3 C 0.5628(2) 0.42037(12) 0.3437(3) 0.0299(5) Uani 1 1 d . . . . .
C4 C 0.1316(3) 0.61974(13) 0.0152(3) 0.0386(5) Uani 1 1 d . . . . .
H4A H 0.2423 0.6070 0.0291 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0939(3) 0.67783(14) 0.0573(3) 0.0419(5) Uani 1 1 d . . . . .
H5 H -0.1724 0.7110 0.0997 0.050 Uiso 1 1 calc R U . . .
H9B H 0.212(3) 0.7628(16) 0.208(4) 0.058(8) Uiso 1 1 d . . . . .
H9A H 0.202(4) 0.6928(18) 0.343(5) 0.088(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.268(3) . ?
N1 O1 1.432(2) . ?
N2 C2 1.300(3) . ?
N2 O2 1.368(2) . ?
N3 C3 1.320(2) . ?
N3 O2 1.408(2) . ?
N4 N5 1.340(2) . ?
N4 C3 1.371(3) . ?
N5 O4 1.241(2) . ?
N5 O3 1.244(2) . ?
N6 C4 1.294(3) . ?
N6 N7 1.353(3) . ?
N7 C5 1.309(3) . ?
N7 H7 0.88(3) . ?
N8 C5 1.320(3) . ?
N8 C4 1.356(3) . ?
N8 N9 1.412(2) . ?
N9 H9B 0.92(3) . ?
N9 H9A 0.95(4) . ?
O1 C1 1.341(2) 3_766 ?
C1 O1 1.341(2) 3_766 ?
C1 C2 1.458(3) . ?
C2 C3 1.444(3) . ?
C4 H4A 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 O1 114.57(16) . . ?
C2 N2 O2 105.40(16) . . ?
C3 N3 O2 105.45(15) . . ?
N5 N4 C3 116.16(16) . . ?
O4 N5 O3 121.64(18) . . ?
O4 N5 N4 122.69(18) . . ?
O3 N5 N4 115.67(18) . . ?
C4 N6 N7 103.35(18) . . ?
C5 N7 N6 112.30(18) . . ?
C5 N7 H7 123.1(18) . . ?
N6 N7 H7 124.5(18) . . ?
C5 N8 C4 106.87(17) . . ?
C5 N8 N9 124.28(18) . . ?
C4 N8 N9 128.85(17) . . ?
N8 N9 H9B 110.0(16) . . ?
N8 N9 H9A 105.1(19) . . ?
H9B N9 H9A 110(3) . . ?
C1 O1 N1 117.39(15) 3_766 . ?
N2 O2 N3 111.33(14) . . ?
N1 C1 O1 128.04(18) . 3_766 ?
N1 C1 C2 119.53(18) . . ?
O1 C1 C2 112.43(17) 3_766 . ?
N2 C2 C3 110.57(17) . . ?
N2 C2 C1 119.56(18) . . ?
C3 C2 C1 129.87(18) . . ?
N3 C3 N4 131.44(18) . . ?
N3 C3 C2 107.24(18) . . ?
N4 C3 C2 121.27(17) . . ?
N6 C4 N8 111.35(19) . . ?
N6 C4 H4A 124.3 . . ?
N8 C4 H4A 124.3 . . ?
N7 C5 N8 106.13(19) . . ?
N7 C5 H5 126.9 . . ?
N8 C5 H5 126.9 . . ?

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
C3 N4 N5 O4 -2.6(3) . . . . ?
C3 N4 N5 O3 177.56(18) . . . . ?
C4 N6 N7 C5 0.4(2) . . . . ?
C1 N1 O1 C1 0.2(3) . . . 3_766 ?
C2 N2 O2 N3 -0.3(2) . . . . ?
C3 N3 O2 N2 -0.2(2) . . . . ?
O1 N1 C1 O1 -0.2(4) . . . 3_766 ?
O1 N1 C1 C2 179.01(18) . . . . ?
O2 N2 C2 C3 0.7(2) . . . . ?
O2 N2 C2 C1 -179.14(17) . . . . ?
N1 C1 C2 N2 172.9(2) . . . . ?
O1 C1 C2 N2 -7.8(3) 3_766 . . . ?
N1 C1 C2 C3 -6.9(3) . . . . ?
O1 C1 C2 C3 172.5(2) 3_766 . . . ?
O2 N3 C3 N4 -176.9(2) . . . . ?
O2 N3 C3 C2 0.6(2) . . . . ?
N5 N4 C3 N3 -7.4(3) . . . . ?
N5 N4 C3 C2 175.35(17) . . . . ?
N2 C2 C3 N3 -0.8(2) . . . . ?
C1 C2 C3 N3 178.94(19) . . . . ?
N2 C2 C3 N4 176.98(18) . . . . ?
C1 C2 C3 N4 -3.2(3) . . . . ?
N7 N6 C4 N8 -0.2(2) . . . . ?
C5 N8 C4 N6 0.0(2) . . . . ?
N9 N8 C4 N6 -179.9(2) . . . . ?
N6 N7 C5 N8 -0.4(2) . . . . ?
C4 N8 C5 N7 0.2(2) . . . . ?
N9 N8 C5 N7 -179.83(19) . . . . ?

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
N9 H9A N4 0.95(4) 2.26(4) 3.165(3) 158(3) 3_666
N9 H9A N1 0.95(4) 2.46(3) 3.096(3) 125(2) 3_666
N9 H9B N4 0.92(3) 2.34(3) 3.251(3) 178(2) 2_655
C5 H5 O4 0.93 2.16 3.067(3) 164.6 2
C4 H4A O2 0.93 2.41 3.225(3) 145.7 .

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

