# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_tw
_database_code_depnum_ccdc_archive 'CCDC 2094116'
loop_
_audit_author_name
_audit_author_address
'Ivan Ananyev'
;Nesmeyanov Insititute of organoelement compounds
Russia
;
_audit_update_record             
;
2021-07-02 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 N7 O6, C3 H7 N8'
_chemical_formula_sum            'C5 H7 N15 O6'
_chemical_formula_weight         373.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.9617(5)
_cell_length_b                   12.9060(6)
_cell_length_c                   10.4101(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.5546(17)
_cell_angle_gamma                90
_cell_volume                     1360.09(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    212
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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            3974
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_v_R_equivalents   ?
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3974
_reflns_number_gt                2475
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²] 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         3974
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
O1A O 0.40791(14) 0.09069(11) 0.61037(15) 0.0335(4) Uani 1 1 d . . . . .
O2A O 0.51065(14) 0.12525(12) 0.47388(14) 0.0339(4) Uani 1 1 d . . . . .
O3A O 0.57622(15) 0.11323(11) 0.91080(15) 0.0324(4) Uani 1 1 d . . . . .
O4A O 0.64962(14) -0.01559(10) 0.82492(14) 0.0309(4) Uani 1 1 d . . . . .
O5A O 0.52279(14) 0.30538(11) 0.66996(16) 0.0340(4) Uani 1 1 d . . . . .
O6A O 0.70065(14) 0.28603(10) 0.85869(14) 0.0299(3) Uani 1 1 d . . . . .
N1A N 0.79298(15) 0.03985(12) 0.65907(16) 0.0218(3) Uani 1 1 d . . . . .
N2A N 0.89502(15) 0.06489(11) 0.62359(16) 0.0216(3) Uani 1 1 d . . . . .
N3A N 0.91120(15) 0.16696(11) 0.62951(16) 0.0202(3) Uani 1 1 d . . . . .
N4A N 0.82079(15) 0.21105(11) 0.66833(16) 0.0184(3) Uani 1 1 d . . . . .
N5A N 0.50340(15) 0.11715(12) 0.58633(17) 0.0225(3) Uani 1 1 d . . . . .
N6A N 0.61912(15) 0.07480(12) 0.82985(16) 0.0226(4) Uani 1 1 d . . . . .
N7A N 0.61512(16) 0.25662(12) 0.75149(17) 0.0232(4) Uani 1 1 d . . . . .
C1A C 0.75088(18) 0.13103(13) 0.68600(18) 0.0171(4) Uani 1 1 d . . . . .
C2A C 0.62968(18) 0.14410(13) 0.71459(19) 0.0188(4) Uani 1 1 d . . . . .
N1C N 0.26130(15) 0.23322(11) 0.78210(17) 0.0223(4) Uani 1 1 d . . . . .
N2C N 0.20557(16) 0.31758(12) 0.82641(17) 0.0219(4) Uani 1 1 d . . . . .
N3C N 0.06826(17) 0.35036(13) 0.95409(18) 0.0238(4) Uani 1 1 d . . . . .
N4C N 0.14324(14) 0.18605(11) 0.90703(16) 0.0179(3) Uani 1 1 d . . . . .
N5C N 0.08521(15) 0.10266(11) 0.94915(16) 0.0200(3) Uani 1 1 d . . . . .
N6C N 0.10766(18) -0.07720(12) 0.91641(19) 0.0238(4) Uani 1 1 d . . . . .
N7C N 0.21287(15) 0.05113(11) 0.83293(16) 0.0204(3) Uani 1 1 d . . . . .
N8C N 0.2653(2) -0.02181(12) 0.7696(2) 0.0293(4) Uani 1 1 d . . . . .
C1C C 0.13365(17) 0.28978(13) 0.89970(18) 0.0180(4) Uani 1 1 d . . . . .
C2C C 0.13097(18) 0.02288(13) 0.90087(19) 0.0189(4) Uani 1 1 d . . . . .
C3C C 0.21731(17) 0.15698(13) 0.83390(19) 0.0183(4) Uani 1 1 d . . . . .
H3NB H 0.061(2) 0.4158(17) 0.937(2) 0.027(6) Uiso 1 1 d . . . . .
H6NB H 0.049(2) -0.0909(15) 0.949(2) 0.023(6) Uiso 1 1 d . . . . .
H2NA H 0.228(3) 0.374(2) 0.814(3) 0.053(8) Uiso 1 1 d . . . . .
H6NA H 0.137(2) -0.1169(18) 0.876(3) 0.037(7) Uiso 1 1 d . . . . .
H3NA H 0.031(2) 0.3252(15) 1.000(2) 0.026(6) Uiso 1 1 d . . . . .
H8NB H 0.237(2) -0.0024(16) 0.679(2) 0.036(7) Uiso 1 1 d . . . . .
H8NA H 0.351(3) -0.0237(19) 0.809(3) 0.050(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
O1A N5A 1.215(2) . ?
O2A N5A 1.208(2) . ?
O3A N6A 1.217(2) . ?
O4A N6A 1.220(2) . ?
O5A N7A 1.217(2) . ?
O6A N7A 1.2108(19) . ?
N1A C1A 1.333(2) . ?
N1A N2A 1.345(2) . ?
N2A N3A 1.3275(19) . ?
N3A N4A 1.333(2) . ?
N4A C1A 1.340(2) . ?
N5A C2A 1.550(2) . ?
N6A C2A 1.536(2) . ?
N7A C2A 1.526(2) . ?
C1A C2A 1.478(2) . ?
N1C C3C 1.300(2) . ?
N1C N2C 1.410(2) . ?
N2C C1C 1.339(2) . ?
N2C H2NA 0.80(3) . ?
N3C C1C 1.326(2) . ?
N3C H3NB 0.86(2) . ?
N3C H3NA 0.81(2) . ?
N4C C1C 1.343(2) . ?
N4C C3C 1.361(2) . ?
N4C N5C 1.4032(19) . ?
N5C C2C 1.326(2) . ?
N6C C2C 1.338(2) . ?
N6C H6NB 0.86(2) . ?
N6C H6NA 0.80(2) . ?
N7C C3C 1.367(2) . ?
N7C C2C 1.388(2) . ?
N7C N8C 1.394(2) . ?
N8C H8NB 0.91(2) . ?
N8C H8NA 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
C1A N1A N2A 103.72(14) . . ?
N3A N2A N1A 109.64(14) . . ?
N2A N3A N4A 109.64(14) . . ?
N3A N4A C1A 104.09(14) . . ?
O2A N5A O1A 127.32(17) . . ?
O2A N5A C2A 116.52(15) . . ?
O1A N5A C2A 116.16(15) . . ?
O3A N6A O4A 127.14(16) . . ?
O3A N6A C2A 117.93(15) . . ?
O4A N6A C2A 114.83(14) . . ?
O6A N7A O5A 128.56(16) . . ?
O6A N7A C2A 114.30(15) . . ?
O5A N7A C2A 117.11(15) . . ?
N1A C1A N4A 112.91(16) . . ?
N1A C1A C2A 123.62(16) . . ?
N4A C1A C2A 123.03(15) . . ?
C1A C2A N7A 110.37(14) . . ?
C1A C2A N6A 115.70(14) . . ?
N7A C2A N6A 108.12(14) . . ?
C1A C2A N5A 112.06(14) . . ?
N7A C2A N5A 106.58(13) . . ?
N6A C2A N5A 103.43(13) . . ?
C3C N1C N2C 99.93(14) . . ?
C1C N2C N1C 113.77(15) . . ?
C1C N2C H2NA 129(2) . . ?
N1C N2C H2NA 117(2) . . ?
C1C N3C H3NB 120.4(14) . . ?
C1C N3C H3NA 119.8(15) . . ?
H3NB N3C H3NA 120(2) . . ?
C1C N4C C3C 107.07(14) . . ?
C1C N4C N5C 138.37(15) . . ?
C3C N4C N5C 113.73(14) . . ?
C2C N5C N4C 101.21(14) . . ?
C2C N6C H6NB 117.0(13) . . ?
C2C N6C H6NA 114.7(17) . . ?
H6NB N6C H6NA 126(2) . . ?
C3C N7C C2C 106.68(14) . . ?
C3C N7C N8C 131.19(15) . . ?
C2C N7C N8C 121.90(15) . . ?
N7C N8C H8NB 105.5(14) . . ?
N7C N8C H8NA 111.5(17) . . ?
H8NB N8C H8NA 112(2) . . ?
N3C C1C N2C 128.19(17) . . ?
N3C C1C N4C 127.39(16) . . ?
N2C C1C N4C 104.42(15) . . ?
N5C C2C N6C 125.88(17) . . ?
N5C C2C N7C 113.69(15) . . ?
N6C C2C N7C 120.39(16) . . ?
N1C C3C N4C 114.77(15) . . ?
N1C C3C N7C 140.44(16) . . ?
N4C C3C N7C 104.62(14) . . ?

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
C1A N1A N2A N3A -0.12(19) . . . . ?
N1A N2A N3A N4A -0.16(19) . . . . ?
N2A N3A N4A C1A 0.37(19) . . . . ?
N2A N1A C1A N4A 0.4(2) . . . . ?
N2A N1A C1A C2A 172.92(17) . . . . ?
N3A N4A C1A N1A -0.5(2) . . . . ?
N3A N4A C1A C2A -173.07(16) . . . . ?
N1A C1A C2A N7A 175.92(16) . . . . ?
N4A C1A C2A N7A -12.3(2) . . . . ?
N1A C1A C2A N6A 52.8(2) . . . . ?
N4A C1A C2A N6A -135.41(17) . . . . ?
N1A C1A C2A N5A -65.5(2) . . . . ?
N4A C1A C2A N5A 106.35(19) . . . . ?
O6A N7A C2A C1A -65.09(19) . . . . ?
O5A N7A C2A C1A 113.38(17) . . . . ?
O6A N7A C2A N6A 62.37(18) . . . . ?
O5A N7A C2A N6A -119.17(16) . . . . ?
O6A N7A C2A N5A 173.01(14) . . . . ?
O5A N7A C2A N5A -8.53(19) . . . . ?
O3A N6A C2A C1A 138.74(17) . . . . ?
O4A N6A C2A C1A -44.7(2) . . . . ?
O3A N6A C2A N7A 14.4(2) . . . . ?
O4A N6A C2A N7A -168.99(15) . . . . ?
O3A N6A C2A N5A -98.34(17) . . . . ?
O4A N6A C2A N5A 78.25(17) . . . . ?
O2A N5A C2A C1A -25.1(2) . . . . ?
O1A N5A C2A C1A 155.29(16) . . . . ?
O2A N5A C2A N7A 95.77(18) . . . . ?
O1A N5A C2A N7A -83.88(17) . . . . ?
O2A N5A C2A N6A -150.35(16) . . . . ?
O1A N5A C2A N6A 29.99(19) . . . . ?
C3C N1C N2C C1C 0.0(2) . . . . ?
C1C N4C N5C C2C 169.2(2) . . . . ?
C3C N4C N5C C2C 1.5(2) . . . . ?
N1C N2C C1C N3C -179.30(18) . . . . ?
N1C N2C C1C N4C 1.2(2) . . . . ?
C3C N4C C1C N3C 178.65(18) . . . . ?
N5C N4C C1C N3C 10.4(4) . . . . ?
C3C N4C C1C N2C -1.8(2) . . . . ?
N5C N4C C1C N2C -170.04(19) . . . . ?
N4C N5C C2C N6C 178.17(18) . . . . ?
N4C N5C C2C N7C 0.2(2) . . . . ?
C3C N7C C2C N5C -1.8(2) . . . . ?
N8C N7C C2C N5C -176.94(18) . . . . ?
C3C N7C C2C N6C -179.90(17) . . . . ?
N8C N7C C2C N6C 5.0(3) . . . . ?
N2C N1C C3C N4C -1.2(2) . . . . ?
N2C N1C C3C N7C 173.0(2) . . . . ?
C1C N4C C3C N1C 2.1(2) . . . . ?
N5C N4C C3C N1C 173.54(16) . . . . ?
C1C N4C C3C N7C -174.14(15) . . . . ?
N5C N4C C3C N7C -2.7(2) . . . . ?
C2C N7C C3C N1C -172.0(2) . . . . ?
N8C N7C C3C N1C 2.5(4) . . . . ?
C2C N7C C3C N4C 2.57(19) . . . . ?
N8C N7C C3C N4C 177.1(2) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.065

_shelxl_version_number           2014/6



