# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 2179754'
loop_
_audit_author_name
_audit_author_address
'Ivan Ananyev'
;Kurnakov Institute of General and Inorganic Chemistry of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;

_vrf_PLAT430_a                   
;
PROBLEM: Short Inter D...A Contact  O5       ..N5       .       2.82 Ang.  
RESPONSE: Geometric criteria suggests the presence of strong
intermolecular O...pi interaction additionally stabilized by 
two weak CH...O H-bonds.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 N6 O9'
_chemical_formula_sum            'C6 H4 N6 O9'
_chemical_formula_weight         304.15

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                   35.7181(13)
_cell_length_b                   5.4680(2)
_cell_length_c                   11.2106(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.986(2)
_cell_angle_gamma                90
_cell_volume                     2186.53(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    242
_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    1.848
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.987
_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            36666
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         30.128
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3208
_reflns_number_gt                2610
_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)+(0.0436P)²+1.0637P] 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         3208
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O4 O 0.25691(2) 0.16420(16) 0.15383(8) 0.01583(19) Uani 1 1 d . . . . .
O3 O 0.30236(3) 0.16823(15) 0.03108(8) 0.01558(19) Uani 1 1 d . . . . .
O2 O 0.28222(2) 0.66984(16) 0.10984(8) 0.01486(19) Uani 1 1 d . . . . .
O1 O 0.32168(3) 0.76007(15) 0.25804(8) 0.01588(19) Uani 1 1 d . . . . .
N1 N 0.35060(3) 0.23167(18) 0.35084(9) 0.0115(2) Uani 1 1 d . . . . .
C3 C 0.31006(3) 0.2835(2) 0.34811(10) 0.0107(2) Uani 1 1 d . . . . .
O5 O 0.36559(3) 0.28283(18) 0.54785(8) 0.0186(2) Uani 1 1 d . . . . .
N3 N 0.28866(3) 0.21364(17) 0.12595(9) 0.0109(2) Uani 1 1 d . . . . .
O6 O 0.47013(3) 0.0736(2) 0.36728(10) 0.0274(2) Uani 1 1 d . . . . .
O7 O 0.41602(3) -0.07815(19) 0.27348(9) 0.0275(2) Uani 1 1 d . . . . .
N2 N 0.30473(3) 0.61768(17) 0.19112(9) 0.0109(2) Uani 1 1 d . . . . .
O8 O 0.42522(3) 0.6876(2) 0.55254(11) 0.0311(3) Uani 1 1 d . . . . .
N4 N 0.42888(3) 0.0650(2) 0.34660(10) 0.0206(2) Uani 1 1 d . . . . .
N5 N 0.47824(3) 0.2376(2) 0.45648(12) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.31284(3) 0.35109(19) 0.21580(10) 0.0091(2) Uani 1 1 d . . . . .
C1 C 0.35467(3) 0.2843(2) 0.22271(11) 0.0120(2) Uani 1 1 d . . . . .
O9 O 0.46372(4) 0.4806(2) 0.67105(10) 0.0382(3) Uani 1 1 d . . . . .
N6 N 0.44507(3) 0.5117(2) 0.57859(11) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.37449(3) 0.2514(2) 0.44542(11) 0.0126(2) Uani 1 1 d . . . . .
C5 C 0.41500(4) 0.2248(2) 0.42199(12) 0.0164(2) Uani 1 1 d . . . . .
C6 C 0.44633(4) 0.3215(3) 0.48730(12) 0.0195(3) Uani 1 1 d . . . . .
H3B H 0.3037(4) 0.414(3) 0.3980(13) 0.012(3) Uiso 1 1 d . . . . .
H1B H 0.3600(4) 0.143(3) 0.1753(14) 0.014(4) Uiso 1 1 d . . . . .
H3A H 0.2944(4) 0.141(3) 0.3615(13) 0.011(3) Uiso 1 1 d . . . . .
H1A H 0.3697(4) 0.417(3) 0.2077(13) 0.013(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
O4 N3 1.2221(13) . ?
O3 N3 1.2193(13) . ?
O2 N2 1.2171(13) . ?
O1 N2 1.2199(13) . ?
N1 C4 1.3303(16) . ?
N1 C3 1.4740(15) . ?
N1 C1 1.4796(15) . ?
C3 C2 1.5369(16) . ?
C3 H3B 0.943(15) . ?
C3 H3A 0.977(15) . ?
O5 C4 1.2194(15) . ?
N3 C2 1.4949(15) . ?
O6 N5 1.3631(17) . ?
O6 N4 1.4804(15) . ?
O7 N4 1.2068(16) . ?
N2 C2 1.5090(14) . ?
O8 N6 1.2211(17) . ?
N4 C5 1.3295(17) . ?
N5 C6 1.2922(18) . ?
C2 C1 1.5362(16) . ?
C1 H1B 0.961(15) . ?
C1 H1A 0.923(15) . ?
O9 N6 1.2145(16) . ?
N6 C6 1.4612(19) . ?
C4 C5 1.4913(17) . ?
C5 C6 1.4081(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C3 126.12(10) . . ?
C4 N1 C1 131.80(10) . . ?
C3 N1 C1 95.09(9) . . ?
N1 C3 C2 87.34(8) . . ?
N1 C3 H3B 113.7(9) . . ?
C2 C3 H3B 114.9(9) . . ?
N1 C3 H3A 114.4(9) . . ?
C2 C3 H3A 114.0(9) . . ?
H3B C3 H3A 110.8(12) . . ?
O3 N3 O4 126.73(10) . . ?
O3 N3 C2 116.49(10) . . ?
O4 N3 C2 116.75(9) . . ?
N5 O6 N4 107.90(9) . . ?
O2 N2 O1 126.73(10) . . ?
O2 N2 C2 118.46(9) . . ?
O1 N2 C2 114.80(9) . . ?
O7 N4 C5 135.79(12) . . ?
O7 N4 O6 117.88(10) . . ?
C5 N4 O6 106.30(11) . . ?
C6 N5 O6 105.86(11) . . ?
N3 C2 N2 105.27(9) . . ?
N3 C2 C1 116.16(9) . . ?
N2 C2 C1 114.57(9) . . ?
N3 C2 C3 117.73(9) . . ?
N2 C2 C3 112.82(9) . . ?
C1 C2 C3 90.32(9) . . ?
N1 C1 C2 87.17(8) . . ?
N1 C1 H1B 114.4(9) . . ?
C2 C1 H1B 112.5(9) . . ?
N1 C1 H1A 114.7(9) . . ?
C2 C1 H1A 112.1(9) . . ?
H1B C1 H1A 113.4(13) . . ?
O9 N6 O8 126.87(14) . . ?
O9 N6 C6 117.55(13) . . ?
O8 N6 C6 115.57(12) . . ?
O5 C4 N1 125.05(11) . . ?
O5 C4 C5 118.84(11) . . ?
N1 C4 C5 116.08(11) . . ?
N4 C5 C6 105.36(11) . . ?
N4 C5 C4 124.99(12) . . ?
C6 C5 C4 128.61(12) . . ?
N5 C6 C5 114.56(13) . . ?
N5 C6 N6 119.99(12) . . ?
C5 C6 N6 125.35(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
C4 N1 C3 C2 151.05(11) . . . . ?
C1 N1 C3 C2 -2.24(9) . . . . ?
N5 O6 N4 O7 -177.14(12) . . . . ?
N5 O6 N4 C5 1.02(14) . . . . ?
N4 O6 N5 C6 -0.24(14) . . . . ?
O3 N3 C2 N2 90.09(11) . . . . ?
O4 N3 C2 N2 -88.01(11) . . . . ?
O3 N3 C2 C1 -37.82(14) . . . . ?
O4 N3 C2 C1 144.08(10) . . . . ?
O3 N3 C2 C3 -143.20(10) . . . . ?
O4 N3 C2 C3 38.70(14) . . . . ?
O2 N2 C2 N3 -0.33(13) . . . . ?
O1 N2 C2 N3 178.77(9) . . . . ?
O2 N2 C2 C1 128.53(11) . . . . ?
O1 N2 C2 C1 -52.38(13) . . . . ?
O2 N2 C2 C3 -129.99(10) . . . . ?
O1 N2 C2 C3 49.11(13) . . . . ?
N1 C3 C2 N3 122.22(10) . . . . ?
N1 C3 C2 N2 -114.82(9) . . . . ?
N1 C3 C2 C1 2.15(8) . . . . ?
C4 N1 C1 C2 -148.61(12) . . . . ?
C3 N1 C1 C2 2.24(9) . . . . ?
N3 C2 C1 N1 -123.55(9) . . . . ?
N2 C2 C1 N1 113.27(10) . . . . ?
C3 C2 C1 N1 -2.14(8) . . . . ?
C3 N1 C4 O5 10.72(19) . . . . ?
C1 N1 C4 O5 153.82(12) . . . . ?
C3 N1 C4 C5 -171.22(10) . . . . ?
C1 N1 C4 C5 -28.12(17) . . . . ?
O7 N4 C5 C6 176.37(15) . . . . ?
O6 N4 C5 C6 -1.30(14) . . . . ?
O7 N4 C5 C4 7.2(2) . . . . ?
O6 N4 C5 C4 -170.48(11) . . . . ?
O5 C4 C5 N4 138.64(13) . . . . ?
N1 C4 C5 N4 -39.55(18) . . . . ?
O5 C4 C5 C6 -28.0(2) . . . . ?
N1 C4 C5 C6 153.85(13) . . . . ?
O6 N5 C6 C5 -0.62(16) . . . . ?
O6 N5 C6 N6 -177.33(11) . . . . ?
N4 C5 C6 N5 1.29(17) . . . . ?
C4 C5 C6 N5 169.94(12) . . . . ?
N4 C5 C6 N6 177.79(12) . . . . ?
C4 C5 C6 N6 -13.6(2) . . . . ?
O9 N6 C6 N5 -48.90(18) . . . . ?
O8 N6 C6 N5 130.65(14) . . . . ?
O9 N6 C6 C5 134.77(14) . . . . ?
O8 N6 C6 C5 -45.67(19) . . . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.053

_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 2179755'
loop_
_audit_author_name
_audit_author_address
'Ivan Ananyev'
;Kurnakov Institute of General and Inorganic Chemistry of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N6 O10'
_chemical_formula_sum            'C5 H6 N6 O10'
_chemical_formula_weight         310.16

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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, z+1/2'

_cell_length_a                   8.5418(5)
_cell_length_b                   7.1633(4)
_cell_length_c                   9.5501(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.7793(16)
_cell_angle_gamma                90
_cell_volume                     572.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    220
_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    1.801
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(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            9582
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         30.045
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3312
_reflns_number_gt                2632
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.987
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.995

_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)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1126 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3312
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
O10 O 0.0447(2) 0.1754(3) 0.5505(3) 0.0488(6) Uani 1 1 d . . . . .
O9 O 0.2030(2) 0.4014(3) 0.5220(2) 0.0381(5) Uani 1 1 d . . . . .
O8 O 0.3720(2) 0.0076(3) 0.2857(2) 0.0308(4) Uani 1 1 d . . . . .
O7 O 0.1642(2) 0.1898(3) 0.25749(18) 0.0306(4) Uani 1 1 d . . . . .
O6 O 0.2876(2) -0.1361(3) 0.6525(2) 0.0422(6) Uani 1 1 d . . . . .
O5 O 0.1520(3) -0.1821(3) 0.4365(2) 0.0436(5) Uani 1 1 d . . . . .
O4 O 0.6798(3) 0.7832(3) 0.4221(2) 0.0426(5) Uani 1 1 d . . . . .
O3 O 0.8226(3) 0.5822(3) 0.3315(2) 0.0448(6) Uani 1 1 d . . . . .
O2 O 0.8567(2) 0.3982(3) 0.74745(19) 0.0363(5) Uani 1 1 d . . . . .
O1 O 0.9545(2) 0.6277(3) 0.6436(2) 0.0328(5) Uani 1 1 d . . . . .
N1 N 0.5188(2) 0.3005(3) 0.4914(2) 0.0181(4) Uani 1 1 d . . . . .
N6 N 0.1671(2) 0.2386(3) 0.5236(2) 0.0260(5) Uani 1 1 d . . . . .
N5 N 0.2736(2) 0.1004(3) 0.3290(2) 0.0200(4) Uani 1 1 d . . . . .
N4 N 0.2371(3) -0.0910(3) 0.5290(2) 0.0269(5) Uani 1 1 d . . . . .
N3 N 0.7411(3) 0.6309(3) 0.4164(2) 0.0287(5) Uani 1 1 d . . . . .
N2 N 0.8560(2) 0.5077(3) 0.6486(2) 0.0215(4) Uani 1 1 d . . . . .
C4 C 0.4597(3) 0.1475(3) 0.5645(2) 0.0190(5) Uani 1 1 d . . . . .
H4B H 0.4619 0.1826 0.6652 0.023 Uiso 1 1 calc R U . . .
H4A H 0.5291 0.0369 0.5643 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2896(3) 0.1005(3) 0.4900(2) 0.0182(5) Uani 1 1 d . . . . .
C1 C 0.6859(3) 0.2858(4) 0.4688(3) 0.0215(5) Uani 1 1 d . . . . .
H1B H 0.6932 0.2704 0.3673 0.026 Uiso 1 1 calc R U . . .
H1A H 0.7511 0.1908 0.5297 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7163(3) 0.4859(3) 0.5244(2) 0.0186(5) Uani 1 1 d . . . . .
C3 C 0.5514(3) 0.4834(3) 0.5649(3) 0.0216(5) Uani 1 1 d . . . . .
H3B H 0.5561 0.4775 0.6693 0.026 Uiso 1 1 calc R U . . .
H3A H 0.4795 0.5848 0.5203 0.026 Uiso 1 1 calc R 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
O10 N6 1.215(3) . ?
O9 N6 1.206(3) . ?
O8 N5 1.209(3) . ?
O7 N5 1.220(3) . ?
O6 N4 1.214(3) . ?
O5 N4 1.214(3) . ?
O4 N3 1.216(3) . ?
O3 N3 1.223(3) . ?
O2 N2 1.227(3) . ?
O1 N2 1.211(3) . ?
N1 C4 1.445(3) . ?
N1 C3 1.485(3) . ?
N1 C1 1.490(3) . ?
N6 C5 1.521(3) . ?
N5 C5 1.516(3) . ?
N4 C5 1.513(3) . ?
N3 C2 1.509(3) . ?
N2 C2 1.509(3) . ?
C4 C5 1.519(3) . ?
C4 H4B 0.9900 . ?
C4 H4A 0.9900 . ?
C1 C2 1.532(3) . ?
C1 H1B 0.9900 . ?
C1 H1A 0.9900 . ?
C2 C3 1.535(3) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C3 119.38(19) . . ?
C4 N1 C1 117.14(19) . . ?
C3 N1 C1 92.20(17) . . ?
O9 N6 O10 126.5(2) . . ?
O9 N6 C5 116.0(2) . . ?
O10 N6 C5 117.5(2) . . ?
O8 N5 O7 127.2(2) . . ?
O8 N5 C5 115.0(2) . . ?
O7 N5 C5 117.9(2) . . ?
O5 N4 O6 127.3(2) . . ?
O5 N4 C5 118.2(2) . . ?
O6 N4 C5 114.6(2) . . ?
O4 N3 O3 126.5(2) . . ?
O4 N3 C2 117.7(2) . . ?
O3 N3 C2 115.8(2) . . ?
O1 N2 O2 126.2(2) . . ?
O1 N2 C2 119.2(2) . . ?
O2 N2 C2 114.6(2) . . ?
N1 C4 C5 109.70(18) . . ?
N1 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
N1 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
H4B C4 H4A 108.2 . . ?
N4 C5 N5 106.22(18) . . ?
N4 C5 C4 112.88(19) . . ?
N5 C5 C4 110.78(18) . . ?
N4 C5 N6 106.69(18) . . ?
N5 C5 N6 106.87(18) . . ?
C4 C5 N6 112.98(19) . . ?
N1 C1 C2 89.02(17) . . ?
N1 C1 H1B 113.8 . . ?
C2 C1 H1B 113.8 . . ?
N1 C1 H1A 113.8 . . ?
C2 C1 H1A 113.8 . . ?
H1B C1 H1A 111.0 . . ?
N2 C2 N3 105.47(18) . . ?
N2 C2 C1 114.87(19) . . ?
N3 C2 C1 116.4(2) . . ?
N2 C2 C3 115.00(18) . . ?
N3 C2 C3 116.4(2) . . ?
C1 C2 C3 88.70(17) . . ?
N1 C3 C2 89.09(17) . . ?
N1 C3 H3B 113.8 . . ?
C2 C3 H3B 113.8 . . ?
N1 C3 H3A 113.8 . . ?
C2 C3 H3A 113.8 . . ?
H3B C3 H3A 111.0 . . ?

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 N1 C4 C5 113.0(2) . . . . ?
C1 N1 C4 C5 -137.3(2) . . . . ?
O5 N4 C5 N5 -21.6(3) . . . . ?
O6 N4 C5 N5 158.1(2) . . . . ?
O5 N4 C5 C4 -143.2(2) . . . . ?
O6 N4 C5 C4 36.5(3) . . . . ?
O5 N4 C5 N6 92.2(3) . . . . ?
O6 N4 C5 N6 -88.2(2) . . . . ?
O8 N5 C5 N4 -71.9(2) . . . . ?
O7 N5 C5 N4 107.2(2) . . . . ?
O8 N5 C5 C4 51.0(3) . . . . ?
O7 N5 C5 C4 -129.9(2) . . . . ?
O8 N5 C5 N6 174.50(19) . . . . ?
O7 N5 C5 N6 -6.4(3) . . . . ?
N1 C4 C5 N4 162.18(18) . . . . ?
N1 C4 C5 N5 43.2(2) . . . . ?
N1 C4 C5 N6 -76.7(2) . . . . ?
O9 N6 C5 N4 168.0(2) . . . . ?
O10 N6 C5 N4 -11.2(3) . . . . ?
O9 N6 C5 N5 -78.7(2) . . . . ?
O10 N6 C5 N5 102.1(2) . . . . ?
O9 N6 C5 C4 43.4(3) . . . . ?
O10 N6 C5 C4 -135.8(2) . . . . ?
C4 N1 C1 C2 -132.46(19) . . . . ?
C3 N1 C1 C2 -7.61(18) . . . . ?
O1 N2 C2 N3 1.1(3) . . . . ?
O2 N2 C2 N3 -179.3(2) . . . . ?
O1 N2 C2 C1 130.6(2) . . . . ?
O2 N2 C2 C1 -49.8(3) . . . . ?
O1 N2 C2 C3 -128.5(2) . . . . ?
O2 N2 C2 C3 51.1(3) . . . . ?
O4 N3 C2 N2 -91.8(2) . . . . ?
O3 N3 C2 N2 87.9(2) . . . . ?
O4 N3 C2 C1 139.6(2) . . . . ?
O3 N3 C2 C1 -40.7(3) . . . . ?
O4 N3 C2 C3 37.1(3) . . . . ?
O3 N3 C2 C3 -143.3(2) . . . . ?
N1 C1 C2 N2 124.46(19) . . . . ?
N1 C1 C2 N3 -111.6(2) . . . . ?
N1 C1 C2 C3 7.36(17) . . . . ?
C4 N1 C3 C2 130.7(2) . . . . ?
C1 N1 C3 C2 7.60(18) . . . . ?
N2 C2 C3 N1 -124.36(19) . . . . ?
N3 C2 C3 N1 111.6(2) . . . . ?
C1 C2 C3 N1 -7.38(18) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047

_shelxl_version_number           2014/6

