# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_cd17131
_database_code_depnum_ccdc_archive 'CCDC 1538054'
_audit_update_record             
;
2017-03-15 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 N8 O9'
_chemical_formula_weight         300.17

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.6849(19)
_cell_length_b                   8.1184(12)
_cell_length_c                   20.797(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.296(3)
_cell_angle_gamma                90
_cell_volume                     2065.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2400
_cell_measurement_theta_min      6.022
_cell_measurement_theta_max      56.350

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6711
_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            5702
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.011
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1923
_reflns_number_gt                1722
_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)+(0.0592P)²+0.8338P] 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         1923
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
O1 O 0.37399(10) 1.10712(14) 0.27375(5) 0.0348(3) Uani 1 1 d . . . . .
O2 O 0.38247(10) 0.44287(14) 0.26261(6) 0.0341(3) Uani 1 1 d . . . . .
O3 O 0.37873(9) 0.65609(15) 0.19853(5) 0.0323(3) Uani 1 1 d . . . . .
O4 O 0.55571(9) 0.76050(15) 0.41365(6) 0.0342(3) Uani 1 1 d . . . . .
O5 O 0.51766(10) 0.72712(17) 0.50765(6) 0.0419(3) Uani 1 1 d . . . . .
O6 O 0.35570(11) 0.89541(16) 0.52404(5) 0.0399(3) Uani 1 1 d . . . . .
O7 O 0.27154(9) 1.05180(14) 0.44235(6) 0.0324(3) Uani 1 1 d . . . . .
O8 O 0.84483(10) 0.99911(17) 0.40500(7) 0.0419(3) Uani 1 1 d . . . . .
O9 O 0.37062(11) 0.71901(16) 0.64818(6) 0.0403(3) Uani 1 1 d . . . . .
N1 N 0.36387(11) 0.94781(17) 0.24785(6) 0.0289(3) Uani 1 1 d . . . . .
N2 N 0.39191(12) 1.10571(16) 0.34192(6) 0.0318(3) Uani 1 1 d . . . . .
N3 N 0.36850(11) 0.68421(16) 0.30444(6) 0.0253(3) Uani 1 1 d . . . . .
N4 N 0.37607(10) 0.59779(16) 0.25285(6) 0.0242(3) Uani 1 1 d . . . . .
N5 N 0.49705(10) 0.78858(16) 0.45182(6) 0.0244(3) Uani 1 1 d . . . . .
N6 N 0.34419(10) 0.94670(16) 0.46591(6) 0.0238(3) Uani 1 1 d . . . . .
N7 N 0.75225(13) 0.9020(2) 0.39815(8) 0.0308(3) Uani 1 1 d . . . . .
N8 N 0.43243(13) 0.6239(2) 0.61538(8) 0.0309(3) Uani 1 1 d . . . . .
C1 C 0.37407(12) 0.85231(19) 0.29975(7) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.39191(12) 0.95231(19) 0.35856(7) 0.0226(3) Uani 1 1 d . . . . .
C3 C 0.40916(12) 0.89478(18) 0.42713(7) 0.0226(3) Uani 1 1 d . . . . .
H8A H 0.499(2) 0.609(3) 0.6412(12) 0.050(6) Uiso 1 1 d . . . . .
H8B H 0.4336(17) 0.676(3) 0.5788(12) 0.047(6) Uiso 1 1 d . . . . .
H7B H 0.7137(18) 0.944(3) 0.4217(11) 0.047(6) Uiso 1 1 d . . . . .
H7A H 0.712(2) 0.892(3) 0.3583(13) 0.058(7) Uiso 1 1 d . . . . .
H7C H 0.776(2) 0.808(3) 0.4125(12) 0.057(7) Uiso 1 1 d . . . . .
H8C H 0.401(2) 0.525(3) 0.6024(12) 0.061(7) Uiso 1 1 d . . . . .
H9 H 0.3806(17) 0.670(3) 0.6869(11) 0.049(6) Uiso 1 1 d . . . . .
H8 H 0.839(2) 1.057(3) 0.3682(14) 0.077(8) 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 N2 1.3754(17) . ?
O1 N1 1.3939(18) . ?
O2 N4 1.2731(17) . ?
O3 N4 1.2336(16) . ?
O4 N5 1.2439(16) . ?
O5 N5 1.2270(17) . ?
O6 N6 1.2503(17) . ?
O7 N6 1.2567(17) . ?
O8 N7 1.3903(19) . ?
O8 H8 0.88(3) . ?
O9 N8 1.3994(19) . ?
O9 H9 0.88(2) . ?
N1 C1 1.307(2) . ?
N2 C2 1.293(2) . ?
N3 N4 1.3064(17) . ?
N3 C1 1.371(2) . ?
N5 C3 1.396(2) . ?
N6 C3 1.3631(19) . ?
N7 H7B 0.85(2) . ?
N7 H7A 0.86(3) . ?
N7 H7C 0.85(3) . ?
N8 H8A 0.88(3) . ?
N8 H8B 0.87(2) . ?
N8 H8C 0.90(3) . ?
C1 C2 1.435(2) . ?
C2 C3 1.461(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
N2 O1 N1 111.35(11) . . ?
N7 O8 H8 109.5(17) . . ?
N8 O9 H9 103.5(14) . . ?
C1 N1 O1 104.60(12) . . ?
C2 N2 O1 105.80(12) . . ?
N4 N3 C1 117.37(12) . . ?
O3 N4 O2 120.60(12) . . ?
O3 N4 N3 124.87(13) . . ?
O2 N4 N3 114.52(12) . . ?
O5 N5 O4 121.02(13) . . ?
O5 N5 C3 123.33(13) . . ?
O4 N5 C3 115.64(12) . . ?
O6 N6 O7 119.32(12) . . ?
O6 N6 C3 122.31(13) . . ?
O7 N6 C3 118.35(12) . . ?
O8 N7 H7B 108.2(15) . . ?
O8 N7 H7A 115.4(16) . . ?
H7B N7 H7A 108(2) . . ?
O8 N7 H7C 105.1(16) . . ?
H7B N7 H7C 112(2) . . ?
H7A N7 H7C 109(2) . . ?
O9 N8 H8A 110.2(14) . . ?
O9 N8 H8B 107.4(15) . . ?
H8A N8 H8B 111(2) . . ?
O9 N8 H8C 112.4(16) . . ?
H8A N8 H8C 110(2) . . ?
H8B N8 H8C 106(2) . . ?
N1 C1 N3 130.77(14) . . ?
N1 C1 C2 109.10(14) . . ?
N3 C1 C2 120.13(13) . . ?
N2 C2 C1 109.15(13) . . ?
N2 C2 C3 123.96(14) . . ?
C1 C2 C3 126.88(14) . . ?
N6 C3 N5 121.49(13) . . ?
N6 C3 C2 121.36(13) . . ?
N5 C3 C2 117.12(12) . . ?

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
N2 O1 N1 C1 0.85(16) . . . . ?
N1 O1 N2 C2 -0.70(16) . . . . ?
C1 N3 N4 O3 -6.3(2) . . . . ?
C1 N3 N4 O2 172.65(13) . . . . ?
O1 N1 C1 N3 178.19(15) . . . . ?
O1 N1 C1 C2 -0.65(16) . . . . ?
N4 N3 C1 N1 15.8(2) . . . . ?
N4 N3 C1 C2 -165.46(13) . . . . ?
O1 N2 C2 C1 0.28(16) . . . . ?
O1 N2 C2 C3 179.51(13) . . . . ?
N1 C1 C2 N2 0.25(18) . . . . ?
N3 C1 C2 N2 -178.73(14) . . . . ?
N1 C1 C2 C3 -178.95(14) . . . . ?
N3 C1 C2 C3 2.1(2) . . . . ?
O6 N6 C3 N5 -4.1(2) . . . . ?
O7 N6 C3 N5 174.76(13) . . . . ?
O6 N6 C3 C2 177.96(14) . . . . ?
O7 N6 C3 C2 -3.2(2) . . . . ?
O5 N5 C3 N6 4.7(2) . . . . ?
O4 N5 C3 N6 -174.34(13) . . . . ?
O5 N5 C3 C2 -177.24(14) . . . . ?
O4 N5 C3 C2 3.7(2) . . . . ?
N2 C2 C3 N6 56.8(2) . . . . ?
C1 C2 C3 N6 -124.08(16) . . . . ?
N2 C2 C3 N5 -121.21(17) . . . . ?
C1 C2 C3 N5 57.9(2) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.048

_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_cd16390
_database_code_depnum_ccdc_archive 'CCDC 1532968'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 N8 O7'
_chemical_formula_weight         268.17

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                   7.588(2)
_cell_length_b                   7.666(2)
_cell_length_c                   10.104(3)
_cell_angle_alpha                105.941(6)
_cell_angle_beta                 91.695(6)
_cell_angle_gamma                114.650(5)
_cell_volume                     506.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    746
_cell_measurement_theta_min      5.990
_cell_measurement_theta_max      50.089

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5498
_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            2910
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.125
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1882
_reflns_number_gt                1455
_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)+(0.0555P)²+0.0980P] 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         1882
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
N1 N 0.5557(3) 0.3029(3) -0.0093(2) 0.0351(5) Uani 1 1 d . . . . .
N2 N 0.4289(3) 0.2212(3) 0.1813(2) 0.0405(6) Uani 1 1 d . . . . .
N3 N 0.8423(3) 0.6182(3) 0.1271(2) 0.0328(5) Uani 1 1 d . . . . .
N4 N 0.9053(3) 0.6583(3) 0.0142(2) 0.0297(5) Uani 1 1 d . . . . .
N5 N 0.7044(3) 0.7044(3) 0.4214(2) 0.0331(5) Uani 1 1 d . . . . .
N6 N 0.7231(3) 0.4126(3) 0.4579(2) 0.0320(5) Uani 1 1 d . . . . .
N7 N 0.9324(5) 0.0968(4) 0.2238(3) 0.0431(6) Uani 1 1 d . . . . .
N8 N 0.2922(5) 0.8392(4) 0.2915(3) 0.0404(6) Uani 1 1 d . . . . .
O1 O 0.4043(3) 0.1625(2) 0.03737(18) 0.0420(5) Uani 1 1 d . . . . .
O2 O 0.8217(3) 0.5551(3) -0.10667(18) 0.0445(5) Uani 1 1 d . . . . .
O3 O 1.0649(2) 0.8208(3) 0.03752(18) 0.0399(5) Uani 1 1 d . . . . .
O4 O 0.6356(3) 0.7643(3) 0.3392(2) 0.0439(5) Uani 1 1 d . . . . .
O5 O 0.7947(4) 0.8186(3) 0.5391(2) 0.0621(7) Uani 1 1 d . . . . .
O6 O 0.8026(3) 0.5032(3) 0.58232(19) 0.0520(6) Uani 1 1 d . . . . .
O7 O 0.6815(3) 0.2262(2) 0.40646(18) 0.0419(5) Uani 1 1 d . . . . .
C1 C 0.6688(3) 0.4435(3) 0.1061(2) 0.0272(5) Uani 1 1 d . . . . .
C2 C 0.5891(3) 0.3910(3) 0.2247(2) 0.0292(6) Uani 1 1 d . . . . .
C3 C 0.6735(3) 0.5021(3) 0.3723(2) 0.0283(6) Uani 1 1 d . . . . .
H1 H 1.035(7) 0.185(7) 0.284(5) 0.103(16) Uiso 1 1 d . . . . .
H2 H 0.917(5) 0.136(5) 0.143(4) 0.065(10) Uiso 1 1 d . . . . .
H3 H 0.918(8) -0.022(8) 0.211(5) 0.13(2) Uiso 1 1 d . . . . .
H4 H 0.831(8) 0.093(7) 0.266(5) 0.124(19) Uiso 1 1 d . . . . .
H5 H 0.182(9) 0.814(8) 0.247(6) 0.15(2) Uiso 1 1 d . . . . .
H6 H 0.276(7) 0.779(7) 0.354(5) 0.119(18) Uiso 1 1 d . . . . .
H7 H 0.364(8) 0.807(8) 0.246(6) 0.14(2) Uiso 1 1 d . . . . .
H8 H 0.354(7) 0.973(7) 0.338(5) 0.116(16) 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 1.318(3) . ?
N1 O1 1.407(3) . ?
N2 C2 1.304(3) . ?
N2 O1 1.380(3) . ?
N3 N4 1.314(3) . ?
N3 C1 1.389(3) . ?
N4 O2 1.235(2) . ?
N4 O3 1.279(2) . ?
N5 O5 1.236(3) . ?
N5 O4 1.248(3) . ?
N5 C3 1.405(3) . ?
N6 O6 1.246(3) . ?
N6 O7 1.272(2) . ?
N6 C3 1.372(3) . ?
N7 H1 0.86(5) . ?
N7 H2 0.97(4) . ?
N7 H3 0.84(5) . ?
N7 H4 0.88(6) . ?
N8 H5 0.85(7) . ?
N8 H6 0.86(5) . ?
N8 H7 0.79(6) . ?
N8 H8 0.90(5) . ?
C1 C2 1.438(3) . ?
C2 C3 1.466(3) . ?

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 104.39(18) . . ?
C2 N2 O1 105.89(19) . . ?
N4 N3 C1 116.23(19) . . ?
O2 N4 O3 120.2(2) . . ?
O2 N4 N3 125.3(2) . . ?
O3 N4 N3 114.53(19) . . ?
O5 N5 O4 121.2(2) . . ?
O5 N5 C3 122.6(2) . . ?
O4 N5 C3 116.2(2) . . ?
O6 N6 O7 119.2(2) . . ?
O6 N6 C3 123.51(19) . . ?
O7 N6 C3 117.3(2) . . ?
H1 N7 H2 113(4) . . ?
H1 N7 H3 112(5) . . ?
H2 N7 H3 118(4) . . ?
H1 N7 H4 106(4) . . ?
H2 N7 H4 105(4) . . ?
H3 N7 H4 101(4) . . ?
H5 N8 H6 111(5) . . ?
H5 N8 H7 116(5) . . ?
H6 N8 H7 105(5) . . ?
H5 N8 H8 108(5) . . ?
H6 N8 H8 107(4) . . ?
H7 N8 H8 109(5) . . ?
N2 O1 N1 111.28(16) . . ?
N1 C1 N3 131.2(2) . . ?
N1 C1 C2 109.3(2) . . ?
N3 C1 C2 119.5(2) . . ?
N2 C2 C1 109.2(2) . . ?
N2 C2 C3 123.9(2) . . ?
C1 C2 C3 126.9(2) . . ?
N6 C3 N5 121.5(2) . . ?
N6 C3 C2 121.19(19) . . ?
N5 C3 C2 117.3(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
C1 N3 N4 O2 0.9(3) . . . . ?
C1 N3 N4 O3 179.7(2) . . . . ?
C2 N2 O1 N1 -0.2(3) . . . . ?
C1 N1 O1 N2 0.0(3) . . . . ?
O1 N1 C1 N3 178.6(2) . . . . ?
O1 N1 C1 C2 0.3(3) . . . . ?
N4 N3 C1 N1 2.6(4) . . . . ?
N4 N3 C1 C2 -179.2(2) . . . . ?
O1 N2 C2 C1 0.4(3) . . . . ?
O1 N2 C2 C3 -177.6(2) . . . . ?
N1 C1 C2 N2 -0.4(3) . . . . ?
N3 C1 C2 N2 -179.0(2) . . . . ?
N1 C1 C2 C3 177.4(2) . . . . ?
N3 C1 C2 C3 -1.1(4) . . . . ?
O6 N6 C3 N5 -2.0(4) . . . . ?
O7 N6 C3 N5 176.8(2) . . . . ?
O6 N6 C3 C2 176.9(2) . . . . ?
O7 N6 C3 C2 -4.3(3) . . . . ?
O5 N5 C3 N6 7.4(4) . . . . ?
O4 N5 C3 N6 -172.8(2) . . . . ?
O5 N5 C3 C2 -171.6(2) . . . . ?
O4 N5 C3 C2 8.2(3) . . . . ?
N2 C2 C3 N6 57.0(3) . . . . ?
C1 C2 C3 N6 -120.5(3) . . . . ?
N2 C2 C3 N5 -124.0(3) . . . . ?
C1 C2 C3 N5 58.5(3) . . . . ?

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
N8 H8 O7 0.90(5) 2.36(5) 3.077(3) 137(4) 1_565
N8 H8 O5 0.90(5) 2.42(5) 3.048(4) 127(4) 2_676
N8 H8 N2 0.90(5) 2.69(4) 3.197(4) 117(3) 1_565
N8 H7 O4 0.79(6) 2.42(6) 2.946(4) 124(5) .
N8 H7 N1 0.79(6) 2.49(6) 3.192(4) 148(5) 2_665
N8 H6 O7 0.86(5) 2.45(5) 3.239(4) 153(4) 2_666
N8 H6 O6 0.86(5) 2.27(5) 3.058(3) 152(4) 2_666
N8 H5 O3 0.85(7) 2.30(6) 2.986(4) 138(5) 1_455
N8 H5 N3 0.85(7) 2.44(6) 3.253(4) 159(5) 1_455
N7 H4 O7 0.88(6) 2.15(6) 2.965(4) 154(4) .
N7 H3 O3 0.84(5) 2.42(5) 2.955(4) 123(4) 1_545
N7 H3 N4 0.84(5) 2.66(5) 3.364(3) 142(4) 1_545
N7 H3 N3 0.84(5) 2.45(5) 3.284(4) 169(5) 1_545
N7 H2 O3 0.97(4) 1.94(4) 2.878(3) 163(3) 2_765
N7 H2 O2 0.97(4) 2.51(3) 3.117(3) 121(2) 2_765
N7 H2 N4 0.97(4) 2.56(4) 3.399(4) 145(3) 2_765
N7 H1 O6 0.86(5) 2.17(5) 2.934(3) 147(4) 2_766
N7 H1 O5 0.86(5) 2.19(5) 2.860(4) 135(4) 2_766

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.055

_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_cd17042
_database_code_depnum_ccdc_archive 'CCDC 1532969'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H14 N14 O7'
_chemical_formula_weight         382.30

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      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A b a 2'
_space_group_name_Hall           'A 2 -2ac'

_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'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   21.595(6)
_cell_length_b                   18.986(6)
_cell_length_c                   7.676(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3147.0(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1360
_cell_measurement_theta_min      4.686
_cell_measurement_theta_max      41.716

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6149
_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            8374
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.886
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.923
_reflns_number_total             2635
_reflns_number_gt                2020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_max     0.889
_reflns_Friedel_fraction_full    0.864

_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)+(0.0822P)²] 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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 688 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.1(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2635
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
O1 O 0.56248(17) 0.84781(17) 0.2717(8) 0.0683(15) Uani 1 1 d . . . . .
O2 O 0.79487(19) 0.9198(2) 0.4638(7) 0.0777(17) Uani 1 1 d . . . . .
O3 O 0.73912(19) 0.82702(19) 0.4118(9) 0.0759(15) Uani 1 1 d . . . . .
O4 O 0.5989(2) 1.0336(3) 0.0229(6) 0.0615(12) Uani 1 1 d . . . . .
O5 O 0.5959(2) 1.1329(2) 0.1587(7) 0.0633(12) Uani 1 1 d . . . . .
O6 O 0.5840(2) 1.0218(2) 0.6010(6) 0.0635(13) Uani 1 1 d . . . . .
O7 O 0.5885(3) 1.1267(2) 0.4933(7) 0.0748(16) Uani 1 1 d . . . . .
N1 N 0.62370(19) 0.8422(2) 0.3297(8) 0.0533(13) Uani 1 1 d . . . . .
N2 N 0.5447(2) 0.9176(2) 0.2624(9) 0.0587(15) Uani 1 1 d . . . . .
N3 N 0.69773(18) 0.9359(2) 0.4023(7) 0.0437(11) Uani 1 1 d . . . . .
N4 N 0.7441(2) 0.8924(2) 0.4264(8) 0.0527(13) Uani 1 1 d . . . . .
N5 N 0.59557(19) 1.0676(2) 0.1619(8) 0.0435(12) Uani 1 1 d . . . . .
N6 N 0.5871(2) 1.0625(3) 0.4729(7) 0.0474(12) Uani 1 1 d . . . . .
N7 N 0.7366(3) 0.6941(2) 0.1694(8) 0.0594(14) Uani 1 1 d . . . . .
H7A H 0.7357 0.7393 0.1670 0.071 Uiso 1 1 calc R U . . .
H7B H 0.7637 0.6716 0.1091 0.071 Uiso 1 1 calc R U . . .
N8 N 0.6549(2) 0.6919(2) 0.3580(7) 0.0579(15) Uani 1 1 d . . . . .
H8A H 0.6534 0.7371 0.3570 0.069 Uiso 1 1 calc R U . . .
H8B H 0.6290 0.6683 0.4200 0.069 Uiso 1 1 calc R U . . .
N9 N 0.6981(2) 0.5893(2) 0.2691(7) 0.0480(12) Uani 1 1 d . . . . .
N10 N 0.7435(2) 0.5543(2) 0.1713(8) 0.0624(15) Uani 1 1 d . . . . .
H10A H 0.7696 0.5781 0.1106 0.075 Uiso 1 1 calc R U . . .
H10B H 0.7453 0.5091 0.1721 0.075 Uiso 1 1 calc R U . . .
N11 N 0.6330(2) 0.7699(3) 0.8662(10) 0.079(2) Uani 1 1 d . . . . .
H11A H 0.6342 0.7247 0.8601 0.095 Uiso 1 1 calc R U . . .
H11B H 0.6657 0.7931 0.8950 0.095 Uiso 1 1 calc R U . . .
N12 N 0.5326(3) 0.7682(3) 0.7886(11) 0.091(2) Uani 1 1 d . . . . .
H12A H 0.4985 0.7899 0.7671 0.109 Uiso 1 1 calc R U . . .
H12B H 0.5342 0.7230 0.7813 0.109 Uiso 1 1 calc R U . . .
N13 N 0.5787(2) 0.8721(2) 0.8425(8) 0.0588(16) Uani 1 1 d . . . . .
N14 N 0.5224(3) 0.9052(3) 0.8145(11) 0.088(2) Uani 1 1 d . . . . .
H14A H 0.4900 0.8806 0.7905 0.106 Uiso 1 1 calc R U . . .
H14B H 0.5198 0.9503 0.8210 0.106 Uiso 1 1 calc R U . . .
C1 C 0.6419(2) 0.9073(2) 0.3524(8) 0.0385(13) Uani 1 1 d . . . . .
C2 C 0.5919(2) 0.9534(2) 0.3071(8) 0.0367(11) Uani 1 1 d . . . . .
C3 C 0.5920(2) 1.0310(2) 0.3135(9) 0.0369(11) Uani 1 1 d . . . . .
C4 C 0.6964(2) 0.6591(2) 0.2657(7) 0.0391(12) Uani 1 1 d . . . . .
C5 C 0.5815(2) 0.8034(3) 0.8318(10) 0.0519(15) Uani 1 1 d . . . . .
H9 H 0.659(3) 0.569(4) 0.281(10) 0.08(2) Uiso 1 1 d . . . . .
H13 H 0.612(3) 0.893(4) 0.879(12) 0.09(3) 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 N2 1.382(5) . ?
O1 N1 1.399(6) . ?
O2 N4 1.246(6) . ?
O3 N4 1.250(5) . ?
O4 N5 1.249(7) . ?
O5 N5 1.240(6) . ?
O6 N6 1.253(6) . ?
O7 N6 1.230(6) . ?
N1 C1 1.307(6) . ?
N2 C2 1.272(6) . ?
N3 N4 1.313(6) . ?
N3 C1 1.377(6) . ?
N5 C3 1.358(8) . ?
N6 C3 1.366(8) . ?
N7 C4 1.320(7) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C4 1.301(7) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 C4 1.325(6) . ?
N9 N10 1.403(7) . ?
N9 H9 0.93(7) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 C5 1.308(7) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 C5 1.294(7) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 C5 1.308(7) . ?
N13 N14 1.386(7) . ?
N13 H13 0.86(7) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
C1 C2 1.434(7) . ?
C2 C3 1.473(6) . ?

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
N2 O1 N1 110.6(3) . . ?
C1 N1 O1 104.8(4) . . ?
C2 N2 O1 106.0(4) . . ?
N4 N3 C1 117.3(4) . . ?
O2 N4 O3 120.8(4) . . ?
O2 N4 N3 116.1(4) . . ?
O3 N4 N3 123.1(5) . . ?
O5 N5 O4 120.0(6) . . ?
O5 N5 C3 122.0(6) . . ?
O4 N5 C3 118.1(4) . . ?
O7 N6 O6 120.9(5) . . ?
O7 N6 C3 123.2(5) . . ?
O6 N6 C3 115.9(4) . . ?
C4 N7 H7A 120.0 . . ?
C4 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C4 N8 H8A 120.0 . . ?
C4 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C4 N9 N10 118.8(5) . . ?
C4 N9 H9 113(4) . . ?
N10 N9 H9 119(4) . . ?
N9 N10 H10A 120.0 . . ?
N9 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C5 N11 H11A 120.0 . . ?
C5 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C5 N12 H12A 120.0 . . ?
C5 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C5 N13 N14 118.9(5) . . ?
C5 N13 H13 116(5) . . ?
N14 N13 H13 124(5) . . ?
N13 N14 H14A 120.0 . . ?
N13 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N1 C1 N3 132.3(4) . . ?
N1 C1 C2 108.6(4) . . ?
N3 C1 C2 119.0(4) . . ?
N2 C2 C1 110.0(4) . . ?
N2 C2 C3 123.0(5) . . ?
C1 C2 C3 127.0(5) . . ?
N5 C3 N6 123.2(4) . . ?
N5 C3 C2 118.9(5) . . ?
N6 C3 C2 117.9(6) . . ?
N8 C4 N7 121.2(4) . . ?
N8 C4 N9 119.1(5) . . ?
N7 C4 N9 119.7(5) . . ?
N12 C5 N13 119.6(6) . . ?
N12 C5 N11 119.6(5) . . ?
N13 C5 N11 120.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 O1 N1 C1 -0.7(6) . . . . ?
N1 O1 N2 C2 1.5(7) . . . . ?
C1 N3 N4 O2 176.9(6) . . . . ?
C1 N3 N4 O3 -2.5(9) . . . . ?
O1 N1 C1 N3 -177.7(6) . . . . ?
O1 N1 C1 C2 -0.4(7) . . . . ?
N4 N3 C1 N1 3.5(10) . . . . ?
N4 N3 C1 C2 -173.6(5) . . . . ?
O1 N2 C2 C1 -1.7(8) . . . . ?
O1 N2 C2 C3 179.7(6) . . . . ?
N1 C1 C2 N2 1.4(8) . . . . ?
N3 C1 C2 N2 179.1(6) . . . . ?
N1 C1 C2 C3 179.9(6) . . . . ?
N3 C1 C2 C3 -2.4(10) . . . . ?
O5 N5 C3 N6 1.4(8) . . . . ?
O4 N5 C3 N6 -178.9(5) . . . . ?
O5 N5 C3 C2 -180.0(5) . . . . ?
O4 N5 C3 C2 -0.3(7) . . . . ?
O7 N6 C3 N5 -3.5(8) . . . . ?
O6 N6 C3 N5 179.7(5) . . . . ?
O7 N6 C3 C2 177.9(5) . . . . ?
O6 N6 C3 C2 1.1(7) . . . . ?
N2 C2 C3 N5 -76.2(8) . . . . ?
C1 C2 C3 N5 105.5(7) . . . . ?
N2 C2 C3 N6 102.4(8) . . . . ?
C1 C2 C3 N6 -75.9(7) . . . . ?
N10 N9 C4 N8 -179.0(6) . . . . ?
N10 N9 C4 N7 0.9(8) . . . . ?
N14 N13 C5 N12 2.8(11) . . . . ?
N14 N13 C5 N11 -176.4(7) . . . . ?

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
N13 H13 O2 0.86(7) 2.18(7) 3.024(7) 165(7) 8_645
N9 H9 O6 0.93(7) 2.31(7) 3.062(7) 138(7) 5_544
N9 H9 O4 0.93(7) 2.37(8) 3.082(7) 134(6) 5_545
N14 H14B O6 0.86 2.57 3.059(8) 116.9 .
N12 H12B O5 0.86 2.36 3.075(7) 140.3 5_545
N12 H12B O1 0.86 2.48 3.013(6) 120.5 6_665
N11 H11B O3 0.86 2.16 2.987(7) 161.6 8_645
N11 H11B O2 0.86 2.61 3.329(6) 142.4 8_645
N11 H11A O7 0.86 2.34 3.044(7) 139.1 5_545
N11 H11A O5 0.86 2.47 3.154(8) 136.7 5_545
N10 H10B N3 0.86 2.56 3.131(7) 124.6 4_645
N10 H10B N3 0.86 2.70 3.209(7) 119.5 5_544
N10 H10B O2 0.86 2.56 3.208(6) 132.4 5_544
N8 H8B O5 0.86 2.08 2.864(7) 151.6 5_545
N8 H8A N1 0.86 2.11 2.941(6) 163.6 .
N8 H8A O3 0.86 2.55 3.172(6) 129.7 .
N7 H7B N8 0.86 2.64 3.347(8) 140.8 8_644
N7 H7A O3 0.86 2.63 3.249(7) 130.1 8_644
N7 H7A O3 0.86 2.51 3.136(7) 130.2 .

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

