# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2249623'
loop_
_audit_author_name
_audit_author_address
'Ivan Ananyev'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_a                   
;
PROBLEM: Short Inter D...A Contact  N3       ..N6       .       2.87 Ang.  
RESPONSE: There is a strong N6...pi intermolecular interaction.
The highest electron density peak near the N6 atom is only 0.11 e.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N7 O6'
_chemical_formula_sum            'C5 H3 N7 O6'
_chemical_formula_weight         257.14

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.2782(3)
_cell_length_b                   6.3430(2)
_cell_length_c                   13.7366(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.6130(10)
_cell_angle_gamma                90
_cell_volume                     950.90(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    333
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11887
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.095
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2533
_reflns_number_gt                2374
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0461P)²+0.3569P] 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         2533
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.58094(7) 0.82012(12) 0.14641(6) 0.02128(17) Uani 1 1 d . . . . .
O2 O 0.62376(7) 0.27708(13) 0.29901(6) 0.02462(18) Uani 1 1 d . . . . .
O3 O 0.53510(7) 0.44512(12) 0.39982(5) 0.02065(16) Uani 1 1 d . . . . .
O4 O 0.13363(6) 1.04648(11) 0.47824(5) 0.01675(15) Uani 1 1 d . . . . .
O5 O 0.19076(9) 1.34890(14) 0.54866(7) 0.0318(2) Uani 1 1 d . . . . .
O6 O 0.33031(7) 1.10852(13) 0.55620(6) 0.02270(17) Uani 1 1 d . . . . .
N1 N 0.62228(8) 0.63650(15) 0.19616(7) 0.01934(18) Uani 1 1 d . . . . .
N2 N 0.48425(8) 0.90525(14) 0.17755(6) 0.01805(18) Uani 1 1 d . . . . .
N3 N 0.57183(7) 0.42864(14) 0.32377(6) 0.01614(17) Uani 1 1 d . . . . .
N4 N 0.36742(7) 0.80472(12) 0.28855(6) 0.01249(16) Uani 1 1 d . . . . .
N5 N 0.25294(7) 0.83085(13) 0.22511(6) 0.01417(16) Uani 1 1 d . . . . .
N6 N 0.17771(7) 0.84375(13) 0.28213(6) 0.01430(16) Uani 1 1 d . . . . .
N7 N 0.22725(8) 1.17754(14) 0.53231(6) 0.01936(18) Uani 1 1 d . . . . .
C1 C 0.55265(8) 0.60939(15) 0.25704(7) 0.01420(18) Uani 1 1 d . . . . .
C2 C 0.46627(8) 0.77607(15) 0.24618(7) 0.01326(18) Uani 1 1 d . . . . .
C3 C 0.36214(8) 0.80133(15) 0.38621(7) 0.01350(18) Uani 1 1 d . . . . .
H3 H 0.4325(13) 0.783(2) 0.4392(11) 0.019(3) Uiso 1 1 d . . . . .
C4 C 0.24052(8) 0.82733(14) 0.38123(7) 0.01311(18) Uani 1 1 d . . . . .
C5 C 0.17563(9) 0.83391(15) 0.46258(7) 0.01516(19) Uani 1 1 d . . . . .
H5B H 0.0991(12) 0.757(2) 0.4447(9) 0.013(3) Uiso 1 1 d . . . . .
H5A H 0.2243(12) 0.780(2) 0.5260(10) 0.018(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 N1 1.3712(12) . ?
O1 N2 1.3781(11) . ?
O2 N3 1.2179(11) . ?
O3 N3 1.2216(11) . ?
O4 N7 1.4007(11) . ?
O4 C5 1.4629(11) . ?
O5 N7 1.2033(12) . ?
O6 N7 1.2074(12) . ?
N1 C1 1.2950(12) . ?
N2 C2 1.3029(12) . ?
N3 C1 1.4497(13) . ?
N4 C3 1.3579(11) . ?
N4 N5 1.3734(11) . ?
N4 C2 1.3936(12) . ?
N5 N6 1.2945(11) . ?
N6 C4 1.3709(12) . ?
C1 C2 1.4198(13) . ?
C3 C4 1.3659(12) . ?
C3 H3 0.939(14) . ?
C4 C5 1.4828(13) . ?
C5 H5B 0.966(13) . ?
C5 H5A 0.968(14) . ?

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
N1 O1 N2 111.98(7) . . ?
N7 O4 C5 113.35(7) . . ?
C1 N1 O1 104.43(8) . . ?
C2 N2 O1 104.95(8) . . ?
O2 N3 O3 126.66(9) . . ?
O2 N3 C1 116.95(8) . . ?
O3 N3 C1 116.38(8) . . ?
C3 N4 N5 111.12(7) . . ?
C3 N4 C2 130.52(8) . . ?
N5 N4 C2 118.27(7) . . ?
N6 N5 N4 106.17(7) . . ?
N5 N6 C4 110.04(8) . . ?
O5 N7 O6 128.90(10) . . ?
O5 N7 O4 112.80(9) . . ?
O6 N7 O4 118.30(8) . . ?
N1 C1 C2 110.19(9) . . ?
N1 C1 N3 119.69(9) . . ?
C2 C1 N3 130.12(8) . . ?
N2 C2 N4 120.47(9) . . ?
N2 C2 C1 108.45(8) . . ?
N4 C2 C1 130.78(8) . . ?
N4 C3 C4 104.03(8) . . ?
N4 C3 H3 121.9(9) . . ?
C4 C3 H3 134.0(9) . . ?
C3 C4 N6 108.65(8) . . ?
C3 C4 C5 130.24(9) . . ?
N6 C4 C5 121.10(8) . . ?
O4 C5 C4 112.11(8) . . ?
O4 C5 H5B 101.5(8) . . ?
C4 C5 H5B 111.9(8) . . ?
O4 C5 H5A 109.0(8) . . ?
C4 C5 H5A 113.2(8) . . ?
H5B C5 H5A 108.5(11) . . ?

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 -0.20(11) . . . . ?
N1 O1 N2 C2 0.25(11) . . . . ?
C3 N4 N5 N6 0.07(10) . . . . ?
C2 N4 N5 N6 176.98(8) . . . . ?
N4 N5 N6 C4 0.19(10) . . . . ?
C5 O4 N7 O5 -176.88(9) . . . . ?
C5 O4 N7 O6 2.94(12) . . . . ?
O1 N1 C1 C2 0.08(11) . . . . ?
O1 N1 C1 N3 -179.11(8) . . . . ?
O2 N3 C1 N1 -23.02(13) . . . . ?
O3 N3 C1 N1 156.29(9) . . . . ?
O2 N3 C1 C2 157.97(10) . . . . ?
O3 N3 C1 C2 -22.71(14) . . . . ?
O1 N2 C2 N4 -174.58(8) . . . . ?
O1 N2 C2 C1 -0.19(10) . . . . ?
C3 N4 C2 N2 -133.24(11) . . . . ?
N5 N4 C2 N2 50.56(12) . . . . ?
C3 N4 C2 C1 53.79(16) . . . . ?
N5 N4 C2 C1 -122.41(11) . . . . ?
N1 C1 C2 N2 0.07(12) . . . . ?
N3 C1 C2 N2 179.15(9) . . . . ?
N1 C1 C2 N4 173.69(9) . . . . ?
N3 C1 C2 N4 -7.24(17) . . . . ?
N5 N4 C3 C4 -0.30(10) . . . . ?
C2 N4 C3 C4 -176.71(9) . . . . ?
N4 C3 C4 N6 0.41(10) . . . . ?
N4 C3 C4 C5 178.91(9) . . . . ?
N5 N6 C4 C3 -0.39(11) . . . . ?
N5 N6 C4 C5 -179.06(8) . . . . ?
N7 O4 C5 C4 -77.63(10) . . . . ?
C3 C4 C5 O4 108.04(11) . . . . ?
N6 C4 C5 O4 -73.61(11) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2249624'
loop_
_audit_author_name
_audit_author_address
'Ivan Ananyev'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N6 O5'
_chemical_formula_sum            'C6 H6 N6 O5'
_chemical_formula_weight         242.17

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                   18.5628(3)
_cell_length_b                   7.92780(10)
_cell_length_c                   13.6589(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.2210(10)
_cell_angle_gamma                90
_cell_volume                     1873.77(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    210
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.143
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25668
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.354
_diffrn_reflns_theta_max         29.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2710
_reflns_number_gt                2598
_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 APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0390P)²+1.5546P] 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         2710
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.41824(4) 0.47435(9) 0.24095(5) 0.01700(14) Uani 1 1 d . . . . .
O2 O 0.28892(4) 0.72636(9) 0.37421(6) 0.02651(17) Uani 1 1 d . . . . .
O3 O 0.35839(4) 0.58256(9) 0.51258(5) 0.02138(15) Uani 1 1 d . . . . .
O4 O 0.26050(3) 0.31240(8) 0.38647(5) 0.01454(13) Uani 1 1 d . . . . .
O5 O 0.37359(3) 0.02390(8) 0.72425(5) 0.01309(13) Uani 1 1 d . . . . .
N1 N 0.37410(4) 0.58697(9) 0.27126(6) 0.01456(14) Uani 1 1 d . . . . .
N2 N 0.44198(4) 0.34123(10) 0.31004(6) 0.01509(15) Uani 1 1 d . . . . .
N3 N 0.33634(4) 0.61857(9) 0.41954(6) 0.01555(15) Uani 1 1 d . . . . .
N4 N 0.42409(4) 0.25825(9) 0.46492(5) 0.01140(14) Uani 1 1 d . . . . .
N5 N 0.49474(4) 0.24345(10) 0.54272(6) 0.01510(15) Uani 1 1 d . . . . .
N6 N 0.48658(4) 0.13198(10) 0.60800(6) 0.01488(15) Uani 1 1 d . . . . .
C1 C 0.37201(4) 0.52524(10) 0.35787(6) 0.01157(15) Uani 1 1 d . . . . .
C2 C 0.41356(4) 0.37134(10) 0.38233(6) 0.01079(15) Uani 1 1 d . . . . .
C3 C 0.37061(4) 0.15588(10) 0.48169(6) 0.01049(14) Uani 1 1 d . . . . .
C4 C 0.41169(4) 0.07561(10) 0.57434(6) 0.01153(15) Uani 1 1 d . . . . .
C5 C 0.28935(4) 0.14489(10) 0.40544(6) 0.01166(15) Uani 1 1 d . . . . .
C6 C 0.38668(5) -0.05070(10) 0.63688(6) 0.01246(15) Uani 1 1 d . . . . .
H5B H 0.2598(7) 0.0760(15) 0.4353(9) 0.013(3) Uiso 1 1 d . . . . .
H6B H 0.3375(7) -0.1032(16) 0.5930(10) 0.015(3) Uiso 1 1 d . . . . .
H5A H 0.2900(7) 0.0958(16) 0.3414(10) 0.017(3) Uiso 1 1 d . . . . .
H6A H 0.4251(7) -0.1372(16) 0.6594(10) 0.016(3) Uiso 1 1 d . . . . .
H5O H 0.4166(9) 0.0562(18) 0.7695(11) 0.026(3) Uiso 1 1 d . . . . .
H4O H 0.2171(9) 0.3147(19) 0.3387(12) 0.031(4) 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 1.3731(10) . ?
O1 N2 1.3775(9) . ?
O2 N3 1.2223(10) . ?
O3 N3 1.2196(10) . ?
O4 C5 1.4203(10) . ?
O4 H4O 0.834(16) . ?
O5 C6 1.4293(10) . ?
O5 H5O 0.854(15) . ?
N1 C1 1.2937(10) . ?
N2 C2 1.2990(10) . ?
N3 C1 1.4488(11) . ?
N4 N5 1.3616(9) . ?
N4 C3 1.3645(10) . ?
N4 C2 1.3981(10) . ?
N5 N6 1.3025(10) . ?
N6 C4 1.3716(10) . ?
C1 C2 1.4172(11) . ?
C3 C4 1.3745(10) . ?
C3 C5 1.4933(11) . ?
C4 C6 1.4949(11) . ?
C5 H5B 0.963(12) . ?
C5 H5A 0.962(13) . ?
C6 H6B 0.985(13) . ?
C6 H6A 0.957(13) . ?

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
N1 O1 N2 111.68(6) . . ?
C5 O4 H4O 110.9(11) . . ?
C6 O5 H5O 109.4(9) . . ?
C1 N1 O1 104.38(7) . . ?
C2 N2 O1 105.23(7) . . ?
O3 N3 O2 126.87(8) . . ?
O3 N3 C1 115.77(7) . . ?
O2 N3 C1 117.35(7) . . ?
N5 N4 C3 111.80(7) . . ?
N5 N4 C2 119.93(7) . . ?
C3 N4 C2 128.25(7) . . ?
N6 N5 N4 105.97(6) . . ?
N5 N6 C4 110.27(7) . . ?
N1 C1 C2 110.33(7) . . ?
N1 C1 N3 120.65(7) . . ?
C2 C1 N3 128.81(7) . . ?
N2 C2 N4 121.25(7) . . ?
N2 C2 C1 108.37(7) . . ?
N4 C2 C1 130.36(7) . . ?
N4 C3 C4 103.60(7) . . ?
N4 C3 C5 122.02(7) . . ?
C4 C3 C5 134.33(7) . . ?
N6 C4 C3 108.36(7) . . ?
N6 C4 C6 120.89(7) . . ?
C3 C4 C6 130.74(7) . . ?
O4 C5 C3 106.96(6) . . ?
O4 C5 H5B 111.9(7) . . ?
C3 C5 H5B 108.9(7) . . ?
O4 C5 H5A 109.9(8) . . ?
C3 C5 H5A 108.4(8) . . ?
H5B C5 H5A 110.7(10) . . ?
O5 C6 C4 112.44(7) . . ?
O5 C6 H6B 106.4(7) . . ?
C4 C6 H6B 110.3(7) . . ?
O5 C6 H6A 111.1(7) . . ?
C4 C6 H6A 108.3(7) . . ?
H6B C6 H6A 108.2(10) . . ?

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 0.97(9) . . . . ?
N1 O1 N2 C2 -0.44(9) . . . . ?
C3 N4 N5 N6 0.46(10) . . . . ?
C2 N4 N5 N6 179.26(7) . . . . ?
N4 N5 N6 C4 -0.60(9) . . . . ?
O1 N1 C1 C2 -1.09(9) . . . . ?
O1 N1 C1 N3 174.05(7) . . . . ?
O3 N3 C1 N1 -156.39(8) . . . . ?
O2 N3 C1 N1 22.23(12) . . . . ?
O3 N3 C1 C2 17.75(12) . . . . ?
O2 N3 C1 C2 -163.63(8) . . . . ?
O1 N2 C2 N4 177.95(7) . . . . ?
O1 N2 C2 C1 -0.24(9) . . . . ?
N5 N4 C2 N2 72.50(10) . . . . ?
C3 N4 C2 N2 -108.92(10) . . . . ?
N5 N4 C2 C1 -109.76(10) . . . . ?
C3 N4 C2 C1 68.83(12) . . . . ?
N1 C1 C2 N2 0.88(10) . . . . ?
N3 C1 C2 N2 -173.74(8) . . . . ?
N1 C1 C2 N4 -177.08(8) . . . . ?
N3 C1 C2 N4 8.29(14) . . . . ?
N5 N4 C3 C4 -0.13(9) . . . . ?
C2 N4 C3 C4 -178.81(8) . . . . ?
N5 N4 C3 C5 -177.86(7) . . . . ?
C2 N4 C3 C5 3.46(13) . . . . ?
N5 N6 C4 C3 0.54(10) . . . . ?
N5 N6 C4 C6 -178.65(7) . . . . ?
N4 C3 C4 N6 -0.24(9) . . . . ?
C5 C3 C4 N6 177.07(8) . . . . ?
N4 C3 C4 C6 178.85(8) . . . . ?
C5 C3 C4 C6 -3.84(15) . . . . ?
N4 C3 C5 O4 -52.63(10) . . . . ?
C4 C3 C5 O4 130.46(9) . . . . ?
N6 C4 C6 O5 78.90(9) . . . . ?
C3 C4 C6 O5 -100.09(10) . . . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6



