# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1580294'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2018-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(H4 N), C4 H2 N10 O4, 3(H2 O)'
_chemical_formula_sum            'C4 H16 N12 O7'
_chemical_formula_weight         344.29

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                   8.8384(9)
_cell_length_b                   20.599(2)
_cell_length_c                   7.5457(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.749(4)
_cell_angle_gamma                90
_cell_volume                     1373.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1417
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.03

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7267
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.875
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2492
_reflns_number_gt                1590
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0509P)²+0.9942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2492
_refine_ls_number_parameters     256
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.1689(4) 0.55377(15) 0.3949(4) 0.0178(7) Uani 1 1 d . . . . .
C2 C 0.0135(4) 0.49349(14) 0.2523(4) 0.0166(7) Uani 1 1 d . . . . .
C3 C -0.0760(4) 0.40568(14) 0.1108(4) 0.0187(7) Uani 1 1 d . . . . .
C4 C 0.1722(4) 0.40156(16) 0.2165(4) 0.0237(8) Uani 1 1 d . . . . .
N1 N 0.0244(3) 0.55217(12) 0.3236(3) 0.0181(6) Uani 1 1 d . . . . .
N2 N 0.2509(3) 0.50009(12) 0.3757(4) 0.0210(7) Uani 1 1 d . . . . .
N3 N 0.1480(3) 0.46184(13) 0.2833(4) 0.0219(7) Uani 1 1 d . . . . .
N4 N -0.1046(3) 0.46635(12) 0.1662(3) 0.0182(6) Uani 1 1 d . . . . .
N5 N 0.0568(3) 0.37312(12) 0.1311(3) 0.0208(7) Uani 1 1 d . . . . .
N6 N 0.2069(3) 0.61235(12) 0.4723(4) 0.0208(7) Uani 1 1 d . . . . .
N7 N 0.3426(3) 0.61810(13) 0.5450(3) 0.0206(6) Uani 1 1 d . . . . .
N8 N -0.1803(3) 0.36536(12) 0.0280(4) 0.0214(7) Uani 1 1 d . . . . .
N9 N -0.3153(3) 0.38676(13) -0.0226(4) 0.0235(7) Uani 1 1 d . . . . .
N10 N 0.3065(3) 0.37488(15) 0.2399(4) 0.0291(8) Uani 1 1 d . . . . .
H10A H 0.323(4) 0.3365(17) 0.199(5) 0.035 Uiso 1 1 d . U . . .
H10B H 0.375(4) 0.3977(19) 0.290(5) 0.035 Uiso 1 1 d . U . . .
N11 N 0.6237(3) 0.54615(13) 0.2428(4) 0.0245(7) Uani 1 1 d D . . . .
H11A H 0.667(3) 0.5847(10) 0.269(4) 0.037 Uiso 1 1 d D U . . .
H11B H 0.690(3) 0.5201(12) 0.191(3) 0.037 Uiso 1 1 d D U . . .
H11C H 0.593(3) 0.5279(13) 0.345(3) 0.037 Uiso 1 1 d D U . . .
H11D H 0.543(3) 0.5524(13) 0.172(3) 0.037 Uiso 1 1 d D U . . .
N12 N 0.1886(4) 0.73819(16) 0.2943(5) 0.0308(8) Uani 1 1 d . . . . .
H12A H 0.190(4) 0.7763(19) 0.367(5) 0.046 Uiso 1 1 d . U . . .
H12B H 0.098(5) 0.7434(18) 0.217(5) 0.046 Uiso 1 1 d . U . . .
H12C H 0.178(5) 0.705(2) 0.361(5) 0.046 Uiso 1 1 d . U . . .
H12D H 0.285(5) 0.7318(18) 0.235(6) 0.046 Uiso 1 1 d . U . . .
O1 O 0.3765(3) 0.67341(11) 0.6036(4) 0.0366(7) Uani 1 1 d . . . . .
O2 O 0.4366(3) 0.57251(10) 0.5592(3) 0.0260(6) Uani 1 1 d . . . . .
O3 O -0.3586(3) 0.44399(11) -0.0091(4) 0.0380(7) Uani 1 1 d . . . . .
O4 O -0.4014(3) 0.34552(11) -0.0949(3) 0.0338(7) Uani 1 1 d . . . . .
O5 O 0.1820(3) 0.34362(12) 0.6590(4) 0.0381(7) Uani 1 1 d D . . . .
H5E H 0.170(5) 0.3278(17) 0.760(3) 0.046 Uiso 1 1 d D U . . .
H5F H 0.118(4) 0.3728(14) 0.656(5) 0.046 Uiso 1 1 d D U . . .
O6 O 0.5889(4) 0.74667(17) 0.8949(5) 0.0746(11) Uani 1 1 d D . . . .
H6E H 0.517(3) 0.750(3) 0.966(5) 0.090 Uiso 1 1 d D U . . .
H6F H 0.662(3) 0.746(2) 0.973(5) 0.090 Uiso 1 1 d D U . . .
O7 O 0.0734(3) 0.25999(13) 0.9233(3) 0.0392(7) Uani 1 1 d D . . . .
H7E H 0.074(5) 0.2899(13) 0.994(4) 0.047 Uiso 1 1 d D U . . .
H7F H 0.109(3) 0.2281(12) 0.975(5) 0.047 Uiso 1 1 d D U . . .


_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
C1 N2 1.331(4) . ?
C1 N6 1.380(4) . ?
C1 N1 1.380(4) . ?
C2 N1 1.326(4) . ?
C2 N4 1.344(4) . ?
C2 N3 1.373(4) . ?
C3 N4 1.343(4) . ?
C3 N5 1.359(4) . ?
C3 N8 1.384(4) . ?
C4 N10 1.318(4) . ?
C4 N5 1.334(4) . ?
C4 N3 1.358(4) . ?
N2 N3 1.385(4) . ?
N6 N7 1.318(3) . ?
N7 O1 1.257(3) . ?
N7 O2 1.257(3) . ?
N8 N9 1.324(4) . ?
N9 O3 1.244(3) . ?
N9 O4 1.260(3) . ?
N10 H10A 0.86(3) . ?
N10 H10B 0.85(4) . ?
N11 H11A 0.902(19) . ?
N11 H11B 0.893(19) . ?
N11 H11C 0.902(19) . ?
N11 H11D 0.898(19) . ?
N12 H12A 0.96(4) . ?
N12 H12B 0.99(4) . ?
N12 H12C 0.86(4) . ?
N12 H12D 0.98(5) . ?
O5 H5E 0.837(18) . ?
O5 H5F 0.827(18) . ?
O6 H6E 0.84(2) . ?
O6 H6F 0.868(19) . ?
O7 H7E 0.816(18) . ?
O7 H7F 0.827(18) . ?

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 C1 N6 130.0(3) . . ?
N2 C1 N1 116.1(3) . . ?
N6 C1 N1 113.9(3) . . ?
N1 C2 N4 128.8(3) . . ?
N1 C2 N3 107.8(3) . . ?
N4 C2 N3 123.4(3) . . ?
N4 C3 N5 126.1(3) . . ?
N4 C3 N8 124.9(3) . . ?
N5 C3 N8 108.9(3) . . ?
N10 C4 N5 124.3(3) . . ?
N10 C4 N3 118.5(3) . . ?
N5 C4 N3 117.2(3) . . ?
C2 N1 C1 104.0(3) . . ?
C1 N2 N3 99.9(2) . . ?
C4 N3 C2 120.7(3) . . ?
C4 N3 N2 126.9(3) . . ?
C2 N3 N2 112.2(3) . . ?
C3 N4 C2 112.9(3) . . ?
C4 N5 C3 119.4(3) . . ?
N7 N6 C1 118.0(2) . . ?
O1 N7 O2 119.6(3) . . ?
O1 N7 N6 116.0(3) . . ?
O2 N7 N6 124.4(3) . . ?
N9 N8 C3 121.5(3) . . ?
O3 N9 O4 119.3(3) . . ?
O3 N9 N8 124.7(3) . . ?
O4 N9 N8 115.9(3) . . ?
C4 N10 H10A 120(2) . . ?
C4 N10 H10B 118(3) . . ?
H10A N10 H10B 123(4) . . ?
H11A N11 H11B 110.2(17) . . ?
H11A N11 H11C 108.3(16) . . ?
H11B N11 H11C 109.6(17) . . ?
H11A N11 H11D 109.7(17) . . ?
H11B N11 H11D 110.3(17) . . ?
H11C N11 H11D 108.7(17) . . ?
H12A N12 H12B 105(3) . . ?
H12A N12 H12C 109(4) . . ?
H12B N12 H12C 110(4) . . ?
H12A N12 H12D 111(3) . . ?
H12B N12 H12D 117(3) . . ?
H12C N12 H12D 105(4) . . ?
H5E O5 H5F 102(3) . . ?
H6E O6 H6F 98(3) . . ?
H7E O7 H7F 107(3) . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1584074'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-08-23 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_1                   
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.35 Note  
RESPONSE: The structure was seriously disordered.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 N10 O4, 2(H2 O)'
_chemical_formula_sum            'C4 H8 N10 O6'
_chemical_formula_weight         292.20

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.9661(7)
_cell_length_b                   6.7936(6)
_cell_length_c                   18.1976(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1108.45(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2821
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      23.30

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5446
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9606
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.743
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2045
_reflns_number_gt                1532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.987

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0693P)²+3.8748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 570 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -5.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     246
_refine_ls_number_restraints     375
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1894
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.096
_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
N6 N 0.4002(11) 0.6399(14) 0.8685(6) 0.026(3) Uani 1 1 d D . . . .
H6A H 0.430(13) 0.743(11) 0.890(6) 0.031 Uiso 1 1 d D U . . .
N7 N 0.4558(14) 0.4653(16) 0.8903(7) 0.030(3) Uani 1 1 d . . . . .
N8 N -0.1520(10) 0.6496(12) 0.6006(5) 0.021(2) Uani 1 1 d D U . . .
H8A H -0.189(12) 0.754(10) 0.582(6) 0.025 Uiso 1 1 d D U . . .
N9 N -0.2049(14) 0.4729(13) 0.5813(6) 0.022(3) Uani 1 1 d . . . . .
O1 O 0.5542(13) 0.4746(13) 0.9378(6) 0.033(2) Uani 1 1 d . . . . .
O2 O 0.4091(10) 0.3135(12) 0.8604(5) 0.035(2) Uani 1 1 d . . . . .
O3 O -0.3047(13) 0.4736(12) 0.5355(6) 0.032(2) Uani 1 1 d . . . . .
O4 O -0.1551(10) 0.3217(11) 0.6091(5) 0.029(2) Uani 1 1 d . U . . .
O5 O 0.4966(12) -0.0295(11) 0.9400(6) 0.027(2) Uani 1 1 d . . . . .
H5C H 0.5756 -0.0158 0.9654 0.033 Uiso 1 1 d R U . . .
H5D H 0.4788 0.0783 0.9180 0.033 Uiso 1 1 d R U . . .
O6 O 0.2448(13) 1.0211(10) 0.0272(5) 0.023(2) Uani 1 1 d D . . . .
H6C H 0.325(7) 0.987(16) 0.009(5) 0.028 Uiso 1 1 d D U . . .
H6D H 0.224(12) 0.924(10) 0.052(5) 0.028 Uiso 1 1 d D U . . .
N1 N 0.218(2) 0.5155(19) 0.7812(11) 0.021(3) Uani 0.779(15) 1 d D U P A 1
C1 C 0.2899(16) 0.665(2) 0.8152(8) 0.021(3) Uani 0.779(15) 1 d D U P A 1
N2 N 0.2604(15) 0.8502(16) 0.7999(7) 0.017(2) Uani 0.779(15) 1 d D U P A 1
N3 N 0.1516(12) 0.8170(15) 0.7477(6) 0.019(2) Uani 0.779(15) 1 d D U P A 1
C2 C 0.130(3) 0.6202(17) 0.7369(13) 0.018(2) Uani 0.779(15) 1 d D U P A 1
N4 N 0.029(2) 0.549(2) 0.6887(10) 0.018(2) Uani 0.779(15) 1 d D U P A 1
C3 C -0.0424(17) 0.692(2) 0.6527(9) 0.019(3) Uani 0.779(15) 1 d D U P A 1
N5 N -0.0256(16) 0.891(2) 0.6599(8) 0.020(2) Uani 0.779(15) 1 d D U P A 1
C4 C 0.0754(14) 0.9541(17) 0.7090(7) 0.020(2) Uani 0.779(15) 1 d D U P A 1
N10 N 0.1010(17) 1.1415(16) 0.7206(8) 0.021(3) Uani 0.779(15) 1 d D U P A 1
H10A H 0.046(13) 1.219(10) 0.695(6) 0.026 Uiso 0.779(15) 1 d D U P A 1
H10B H 0.175(13) 1.166(13) 0.749(8) 0.026 Uiso 0.779(15) 1 d D U P A 1
N1' N 0.026(7) 0.518(6) 0.688(3) 0.020(5) Uiso 0.221(15) 1 d D U P A 2
C1' C -0.045(4) 0.671(8) 0.655(2) 0.020(5) Uiso 0.221(15) 1 d D U P A 2
N2' N -0.017(5) 0.856(7) 0.670(2) 0.021(5) Uiso 0.221(15) 1 d D U P A 2
N3' N 0.096(4) 0.820(4) 0.7202(18) 0.017(4) Uiso 0.221(15) 1 d D U P A 2
C2' C 0.118(7) 0.623(5) 0.730(4) 0.018(4) Uiso 0.221(15) 1 d D U P A 2
N4' N 0.213(7) 0.550(6) 0.781(3) 0.019(4) Uiso 0.221(15) 1 d D U P A 2
C3' C 0.292(6) 0.691(7) 0.816(3) 0.020(4) Uiso 0.221(15) 1 d D U P A 2
N5' N 0.272(5) 0.890(6) 0.809(3) 0.019(5) Uiso 0.221(15) 1 d D U P A 2
C4' C 0.170(4) 0.955(5) 0.761(2) 0.018(4) Uiso 0.221(15) 1 d D U P A 2
N10' N 0.142(4) 1.144(4) 0.750(2) 0.014(8) Uiso 0.221(15) 1 d D U P A 2
H10C H 0.20(3) 1.221(11) 0.776(16) 0.017 Uiso 0.221(15) 1 d D U P A 2
H10D H 0.10(5) 1.167(16) 0.708(12) 0.017 Uiso 0.221(15) 1 d D U P A 2


_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
N6 N7 1.347(15) . ?
N6 C1 1.395(15) . ?
N6 C3' 1.40(2) . ?
N6 H6A 0.85(3) . ?
N7 O1 1.236(16) . ?
N7 O2 1.240(14) . ?
N8 N9 1.337(13) . ?
N8 C1' 1.39(2) . ?
N8 C3 1.396(14) . ?
N8 H8A 0.85(3) . ?
N9 O3 1.223(15) . ?
N9 O4 1.229(12) . ?
O5 H5C 0.8501 . ?
O5 H5D 0.8499 . ?
O6 H6C 0.82(3) . ?
O6 H6D 0.82(3) . ?
N1 C2 1.34(2) . ?
N1 C1 1.349(19) . ?
C1 N2 1.318(17) . ?
N2 N3 1.379(16) . ?
N3 C4 1.353(13) . ?
N3 C2 1.365(13) . ?
C2 N4 1.35(2) . ?
N4 C3 1.335(19) . ?
C3 N5 1.364(19) . ?
N5 C4 1.343(18) . ?
C4 N10 1.311(15) . ?
N10 H10A 0.86(3) . ?
N10 H10B 0.86(3) . ?
N1' C2' 1.34(4) . ?
N1' C1' 1.35(3) . ?
C1' N2' 1.31(3) . ?
C1' C2' 2.03(4) . ?
N2' N3' 1.38(3) . ?
N3' C4' 1.36(2) . ?
N3' C2' 1.37(2) . ?
C2' N4' 1.35(4) . ?
N4' C3' 1.35(3) . ?
C3' N5' 1.37(3) . ?
N5' C4' 1.34(3) . ?
C4' N10' 1.32(3) . ?
N10' H10C 0.86(3) . ?
N10' H10D 0.87(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
N7 N6 C1 125.0(11) . . ?
N7 N6 C3' 132(2) . . ?
N7 N6 H6A 118(8) . . ?
C1 N6 H6A 117(8) . . ?
C3' N6 H6A 110(8) . . ?
O1 N7 O2 126.3(12) . . ?
O1 N7 N6 115.2(11) . . ?
O2 N7 N6 118.5(12) . . ?
N9 N8 C1' 122(3) . . ?
N9 N8 C3 127.8(11) . . ?
N9 N8 H8A 120(8) . . ?
C1' N8 H8A 118(8) . . ?
C3 N8 H8A 112(8) . . ?
O3 N9 O4 123.4(10) . . ?
O3 N9 N8 115.7(10) . . ?
O4 N9 N8 120.9(11) . . ?
H5C O5 H5D 108.6 . . ?
H6C O6 H6D 101(10) . . ?
C2 N1 C1 99.2(12) . . ?
N2 C1 N1 121.7(12) . . ?
N2 C1 N6 113.9(12) . . ?
N1 C1 N6 124.5(13) . . ?
C1 N2 N3 97.5(9) . . ?
C4 N3 C2 121.8(12) . . ?
C4 N3 N2 127.1(10) . . ?
C2 N3 N2 111.1(12) . . ?
N1 C2 N4 126.9(11) . . ?
N1 C2 N3 110.5(16) . . ?
N4 C2 N3 122.6(15) . . ?
C3 N4 C2 112.4(12) . . ?
N4 C3 N5 128.2(12) . . ?
N4 C3 N8 121.5(14) . . ?
N5 C3 N8 110.3(12) . . ?
C4 N5 C3 117.1(11) . . ?
N10 C4 N5 122.5(12) . . ?
N10 C4 N3 119.8(11) . . ?
N5 C4 N3 117.8(11) . . ?
C4 N10 H10A 114(6) . . ?
C4 N10 H10B 115(6) . . ?
H10A N10 H10B 131(10) . . ?
C2' N1' C1' 98(2) . . ?
N2' C1' N1' 124(3) . . ?
N2' C1' N8 112(4) . . ?
N1' C1' N8 124(4) . . ?
N2' C1' C2' 82.7(18) . . ?
N1' C1' C2' 40.8(15) . . ?
N8 C1' C2' 165(4) . . ?
C1' N2' N3' 96(2) . . ?
C4' N3' C2' 121(3) . . ?
C4' N3' N2' 127(3) . . ?
C2' N3' N2' 111(2) . . ?
N1' C2' N4' 127(3) . . ?
N1' C2' N3' 111(3) . . ?
N4' C2' N3' 123(3) . . ?
N1' C2' C1' 41.3(16) . . ?
N4' C2' C1' 167(4) . . ?
N3' C2' C1' 69.4(18) . . ?
C3' N4' C2' 114(3) . . ?
N4' C3' N5' 126(3) . . ?
N4' C3' N6 121(3) . . ?
N5' C3' N6 113(3) . . ?
C4' N5' C3' 119(3) . . ?
N10' C4' N5' 123(3) . . ?
N10' C4' N3' 119(2) . . ?
N5' C4' N3' 118(2) . . ?
C4' N10' H10C 113(7) . . ?
C4' N10' H10D 113(7) . . ?
H10C N10' H10D 129(10) . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.086

