# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1825381'
loop_
_audit_author_name
_audit_author_address
'hualin xiong' 'Nanjing University of Science and Technology'
_audit_update_record             
;
2018-02-23 deposited with the CCDC.	2019-09-03 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), C8 N14 O10, 2(H2 O)'
_chemical_formula_sum            'C8 H12 N16 O12'
_chemical_formula_weight         524.34

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                   29.577(3)
_cell_length_b                   5.0295(4)
_cell_length_c                   14.2565(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.983(3)
_cell_angle_gamma                90
_cell_volume                     2117.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1566
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      25.31

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6789
_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            6910
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.111
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1836
_reflns_number_gt                1227
_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)+(0.0956P)²+4.9691P] 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_number_reflns         1836
_refine_ls_number_parameters     181
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2079
_refine_ls_wR_factor_gt          0.1790
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.162
_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
C1 C 0.40169(15) 0.4032(8) 0.4599(3) 0.0276(10) Uani 1 1 d . . . . .
C2 C 0.44672(15) 0.3527(8) 0.4924(2) 0.0296(10) Uani 1 1 d . . . . .
C3 C 0.38107(14) 0.6004(8) 0.3966(3) 0.0274(10) Uani 1 1 d . . . . .
C4 C 0.37453(14) 0.9125(8) 0.3014(3) 0.0273(10) Uani 1 1 d . . . . .
N1 N 0.48475(13) 0.5000(7) 0.4677(2) 0.0311(9) Uani 1 1 d . . . . .
N2 N 0.37680(14) 0.2153(8) 0.4993(2) 0.0364(10) Uani 1 1 d . . . . .
N3 N 0.45074(14) 0.1434(7) 0.5470(2) 0.0366(10) Uani 1 1 d . . . . .
N4 N 0.33765(14) 0.5991(8) 0.3755(3) 0.0453(11) Uani 1 1 d . . . . .
N5 N 0.40601(12) 0.7887(7) 0.3532(2) 0.0259(8) Uani 1 1 d . . . . .
N6 N 0.37232(13) 1.1204(8) 0.2405(2) 0.0343(9) Uani 1 1 d . . . . .
N7 N 0.41059(14) 1.2510(7) 0.2268(2) 0.0327(9) Uani 1 1 d . . . . .
O1 O 0.40793(12) 0.0457(6) 0.55439(19) 0.0403(9) Uani 1 1 d . . . . .
O2 O 0.33700(13) 0.1571(7) 0.4975(3) 0.0529(10) Uani 1 1 d . . . . .
O3 O 0.33292(11) 0.8096(7) 0.3106(2) 0.0453(9) Uani 1 1 d . . . . .
O4 O 0.40712(13) 1.4443(6) 0.1719(2) 0.0442(9) Uani 1 1 d . . . . .
O5 O 0.44783(11) 1.1911(6) 0.2664(2) 0.0403(8) Uani 1 1 d . . . . .
N8 N 1.0000 0.1948(10) 0.2500 0.0272(11) Uani 1 2 d DS T P . .
H8A H 1.0186(17) 0.341(9) 0.231(4) 0.041 Uiso 0.5 1 d D U P . .
H8B H 1.0181(16) 0.035(9) 0.256(4) 0.041 Uiso 0.5 1 d D U P . .
H8C H 0.988(2) 0.237(11) 0.310(3) 0.041 Uiso 0.5 1 d D U P . .
H8D H 0.9755(18) 0.166(10) 0.204(4) 0.041 Uiso 0.5 1 d D U P . .
N9 N 0.2497(5) 0.792(3) 0.0965(17) 0.017(6) Uiso 0.21(2) 1 d . . P A 1
H9A H 0.2547 0.6693 0.1420 0.026 Uiso 0.21(2) 1 d R U P A 1
H9B H 0.2456 0.9479 0.1257 0.026 Uiso 0.21(2) 1 d R U P A 1
H9C H 0.2250 0.7490 0.0602 0.026 Uiso 0.21(2) 1 d R U P A 1
H9D H 0.2736 0.8014 0.0600 0.026 Uiso 0.21(2) 1 d R U P A 1
N9' N 0.2482(4) 0.781(2) 0.1415(14) 0.029(4) Uiso 0.29(2) 1 d . . P A 2
H9'A H 0.2668 0.9205 0.1350 0.043 Uiso 0.29(2) 1 d R U P A 2
H9'B H 0.2249 0.7956 0.0986 0.043 Uiso 0.29(2) 1 d R U P A 2
H9'C H 0.2378 0.7794 0.1997 0.043 Uiso 0.29(2) 1 d R U P A 2
H9'D H 0.2632 0.6282 0.1327 0.043 Uiso 0.29(2) 1 d R U P A 2
O6 O 0.2829(3) 0.2728(17) 0.1764(6) 0.072(2) Uiso 0.556(3) 1 d . . P B 3
H6A H 0.2845 0.3885 0.1332 0.086 Uiso 0.556(3) 1 d R U P B 3
H6B H 0.3093 0.2223 0.1950 0.086 Uiso 0.556(3) 1 d R U P B 3
O6' O 0.2938(5) 0.309(3) 0.1186(11) 0.112(4) Uiso 0.444(3) 1 d . . P B 4
H6'A H 0.3012 0.3419 0.0629 0.135 Uiso 0.444(3) 1 d R U P B 4
H6'B H 0.3178 0.2738 0.1515 0.135 Uiso 0.444(3) 1 d R U P B 4


_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 1.339(6) . ?
C1 C2 1.410(6) . ?
C1 C3 1.454(6) . ?
C2 N3 1.311(5) . ?
C2 N1 1.407(6) . ?
C3 N4 1.304(6) . ?
C3 N5 1.368(5) . ?
C4 N5 1.315(5) . ?
C4 O3 1.348(5) . ?
C4 N6 1.358(5) . ?
N1 N1 1.256(7) 5_666 ?
N2 O2 1.212(5) . ?
N2 O1 1.455(5) . ?
N3 O1 1.367(5) . ?
N4 O3 1.408(5) . ?
N6 N7 1.332(5) . ?
N7 O4 1.249(5) . ?
N7 O5 1.249(5) . ?

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 C2 105.4(4) . . ?
N2 C1 C3 121.3(4) . . ?
C2 C1 C3 133.3(4) . . ?
N3 C2 N1 121.5(4) . . ?
N3 C2 C1 113.2(4) . . ?
N1 C2 C1 125.2(4) . . ?
N4 C3 N5 116.6(4) . . ?
N4 C3 C1 121.1(4) . . ?
N5 C3 C1 122.3(4) . . ?
N5 C4 O3 112.7(4) . . ?
N5 C4 N6 137.1(4) . . ?
O3 C4 N6 110.1(4) . . ?
N1 N1 C2 111.6(4) 5_666 . ?
O2 N2 C1 135.7(4) . . ?
O2 N2 O1 117.2(4) . . ?
C1 N2 O1 107.1(4) . . ?
C2 N3 O1 106.2(4) . . ?
C3 N4 O3 102.2(3) . . ?
C4 N5 C3 101.5(3) . . ?
N7 N6 C4 117.4(4) . . ?
O4 N7 O5 120.9(4) . . ?
O4 N7 N6 115.7(4) . . ?
O5 N7 N6 123.4(4) . . ?
N3 O1 N2 108.1(3) . . ?
C4 O3 N4 107.0(3) . . ?

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_22019213_0m
_database_code_depnum_ccdc_archive 'CCDC 1936651'
loop_
_audit_author_name
_audit_author_address
'hualin xiong'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-06-26 deposited with the CCDC.	2019-09-03 downloaded from the CCDC.
;
_audit_creation_date             2019-03-11
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H2 N10 O8, C3 H6 O'
_chemical_formula_sum            'C11 H8 N10 O9'
_chemical_formula_weight         424.27
_chemical_melting_point          ?
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.572(3)
_cell_length_b                   11.493(2)
_cell_length_c                   9.5435(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.872(7)
_cell_angle_gamma         