# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_0927-1
_database_code_depnum_ccdc_archive 'CCDC 2306222'
loop_
_audit_author_name
_audit_author_address
liu
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2022-10-01
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N6 O5, H2 O'
_chemical_formula_sum            'C6 H6 N6 O6'
_chemical_formula_weight         258.17
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.1700(2)
_cell_length_b                   6.5296(2)
_cell_length_c                   15.4974(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.747(2)
_cell_angle_gamma                90
_cell_volume                     919.46(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2197
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      72.9240
_cell_measurement_theta_min      5.7550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3074
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.046
_diffrn_reflns_theta_min         5.312
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  33.00   1.00    1.00    --  -40.73  38.00  30.00   25
  2  ω    -62.00  -7.00   1.00    1.00    --  -40.73  38.00  30.00   55
  3  ω    -61.00  -9.00   1.00    1.00    --  -40.73  77.00  90.00   52
  4  ω     21.00 110.00   1.00    1.00    --   40.73  57.00-180.00   89
  5  ω     34.00  96.00   1.00    1.00    --  106.95 -45.00-120.00   62
  6  ω     91.00 155.00   1.00    1.00    --  106.95  45.00   0.00   64
  7  ω    144.00 171.00   1.00    1.00    --  106.95 125.00   0.00   27
  8  ω     35.00 118.00   1.00    1.00    --  106.95 -45.00 150.00   83
  9  ω     35.00 106.00   1.00    1.00    --  106.95 -95.00 120.00   71
 10  ω     37.00 113.00   1.00    1.00    --  106.95-125.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0943627000
_diffrn_orient_matrix_UB_12      0.1060854000
_diffrn_orient_matrix_UB_13      -0.0619351000
_diffrn_orient_matrix_UB_21      0.0191479000
_diffrn_orient_matrix_UB_22      -0.2063224000
_diffrn_orient_matrix_UB_23      -0.0454490000
_diffrn_orient_matrix_UB_31      -0.1394905000
_diffrn_orient_matrix_UB_32      0.0432852000
_diffrn_orient_matrix_UB_33      -0.0645198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1612
_reflns_number_total             1769
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.3480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.35624(13) 0.86167(18) 0.23950(7) 0.0301(3) Uani 1 1 d . . . . .
O2 O 0.45689(12) 0.58470(17) 0.29784(7) 0.0280(3) Uani 1 1 d . . . . .
O3 O 0.39073(12) 0.16023(18) 0.54416(7) 0.0289(3) Uani 1 1 d . . . . .
O4 O 0.24188(17) 0.1442(2) 0.67781(10) 0.0527(4) Uani 1 1 d . . . . .
O5 O 0.07919(13) 0.37404(18) 0.69201(7) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.37225(13) 0.73139(19) 0.29784(8) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.13370(14) 0.8798(2) 0.45395(8) 0.0238(3) Uani 1 1 d . . . . .
N3 N 0.18682(13) 0.68933(19) 0.48310(8) 0.0193(3) Uani 1 1 d . . . . .
N4 N 0.34313(13) 0.42416(19) 0.45316(8) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.399979 0.369432 0.417926 0.025 Uiso 1 1 calc R U . . .
N5 N 0.05976(15) 0.7082(2) 0.59923(9) 0.0254(3) Uani 1 1 d . . . . .
H5A H 0.037(2) 0.829(3) 0.5796(13) 0.033(5) Uiso 1 1 d . . . . .
H5B H 0.037(2) 0.660(3) 0.6458(14) 0.041(6) Uiso 1 1 d . . . . .
N6 N 0.17892(14) 0.3022(2) 0.65374(8) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.19657(17) 0.9117(2) 0.38410(10) 0.0239(3) Uani 1 1 d . . . . .
H1 H 0.181555 1.031124 0.349000 0.029 Uiso 1 1 calc R U . . .
C2 C 0.28866(15) 0.7492(2) 0.36709(9) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.28131(15) 0.6072(2) 0.43252(9) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.32084(16) 0.3173(2) 0.52818(9) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.21428(16) 0.4083(2) 0.57889(9) 0.0207(3) Uani 1 1 d . . . . .
C6 C 0.15014(15) 0.6003(2) 0.55845(9) 0.0193(3) Uani 1 1 d . . . . .
O6 O 0.54659(13) 0.21151(18) 0.37593(7) 0.0298(3) Uani 1 1 d G . . . .
H6A H 0.572151 0.092249 0.394090 0.045 Uiso 1 1 d G U . . .
H6B H 0.557081 0.210004 0.322277 0.045 Uiso 1 1 d G 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
O1 N1 1.2357(17) . ?
O2 N1 1.2328(16) . ?
O3 C4 1.2172(18) . ?
O4 N6 1.2161(18) . ?
O5 N6 1.2468(17) . ?
N1 C2 1.4052(18) . ?
N2 N3 1.3888(17) . ?
N2 C1 1.310(2) . ?
N3 C3 1.3549(18) . ?
N3 C6 1.3857(18) . ?
N4 H4 0.8800 . ?
N4 C3 1.3430(19) . ?
N4 C4 1.3943(19) . ?
N5 H5A 0.86(2) . ?
N5 H5B 0.84(2) . ?
N5 C6 1.3132(19) . ?
N6 C5 1.4254(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.403(2) . ?
C2 C3 1.382(2) . ?
C4 C5 1.460(2) . ?
C5 C6 1.403(2) . ?
O6 H6A 0.8502 . ?
O6 H6B 0.8499 . ?

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
O1 N1 C2 118.60(12) . . ?
O2 N1 O1 123.21(12) . . ?
O2 N1 C2 118.18(12) . . ?
C1 N2 N3 103.72(12) . . ?
C3 N3 N2 112.94(12) . . ?
C3 N3 C6 124.63(13) . . ?
C6 N3 N2 122.38(12) . . ?
C3 N4 H4 118.7 . . ?
C3 N4 C4 122.63(12) . . ?
C4 N4 H4 118.7 . . ?
H5A N5 H5B 125(2) . . ?
C6 N5 H5A 117.3(14) . . ?
C6 N5 H5B 117.2(15) . . ?
O4 N6 O5 121.44(13) . . ?
O4 N6 C5 120.74(13) . . ?
O5 N6 C5 117.79(13) . . ?
N2 C1 H1 123.9 . . ?
N2 C1 C2 112.20(14) . . ?
C2 C1 H1 123.9 . . ?
C1 C2 N1 127.58(14) . . ?
C3 C2 N1 126.20(13) . . ?
C3 C2 C1 106.22(13) . . ?
N3 C3 C2 104.92(12) . . ?
N4 C3 N3 119.78(13) . . ?
N4 C3 C2 135.30(13) . . ?
O3 C4 N4 117.31(13) . . ?
O3 C4 C5 127.26(14) . . ?
N4 C4 C5 115.43(13) . . ?
N6 C5 C4 118.85(13) . . ?
C6 C5 N6 118.92(13) . . ?
C6 C5 C4 122.17(13) . . ?
N3 C6 C5 115.04(13) . . ?
N5 C6 N3 114.89(14) . . ?
N5 C6 C5 130.06(14) . . ?
H6A O6 H6B 104.5 . . ?

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
O1 N1 C2 C1 -7.1(2) . . . . ?
O1 N1 C2 C3 172.87(14) . . . . ?
O2 N1 C2 C1 173.78(14) . . . . ?
O2 N1 C2 C3 -6.3(2) . . . . ?
O3 C4 C5 N6 -3.3(2) . . . . ?
O3 C4 C5 C6 174.00(15) . . . . ?
O4 N6 C5 C4 3.9(2) . . . . ?
O4 N6 C5 C6 -173.57(15) . . . . ?
O5 N6 C5 C4 -174.35(13) . . . . ?
O5 N6 C5 C6 8.2(2) . . . . ?
N1 C2 C3 N3 -179.37(13) . . . . ?
N1 C2 C3 N4 0.7(3) . . . . ?
N2 N3 C3 N4 179.25(12) . . . . ?
N2 N3 C3 C2 -0.71(16) . . . . ?
N2 N3 C6 N5 1.0(2) . . . . ?
N2 N3 C6 C5 -179.50(12) . . . . ?
N2 C1 C2 N1 179.66(14) . . . . ?
N2 C1 C2 C3 -0.28(18) . . . . ?
N3 N2 C1 C2 -0.14(17) . . . . ?
N4 C4 C5 N6 176.39(12) . . . . ?
N4 C4 C5 C6 -6.3(2) . . . . ?
N6 C5 C6 N3 -177.97(12) . . . . ?
N6 C5 C6 N5 1.4(2) . . . . ?
C1 N2 N3 C3 0.54(16) . . . . ?
C1 N2 N3 C6 177.90(13) . . . . ?
C1 C2 C3 N3 0.58(16) . . . . ?
C1 C2 C3 N4 -179.37(16) . . . . ?
C3 N3 C6 N5 178.05(13) . . . . ?
C3 N3 C6 C5 -2.5(2) . . . . ?
C3 N4 C4 O3 -174.57(13) . . . . ?
C3 N4 C4 C5 5.7(2) . . . . ?
C4 N4 C3 N3 -3.7(2) . . . . ?
C4 N4 C3 C2 176.24(15) . . . . ?
C4 C5 C6 N3 4.7(2) . . . . ?
C4 C5 C6 N5 -175.92(15) . . . . ?
C6 N3 C3 N4 2.0(2) . . . . ?
C6 N3 C3 C2 -178.00(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.800
_oxdiff_exptl_absorpt_empirical_full_min 0.557
####################################################################### 
# 
# 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_20220607
_database_code_depnum_ccdc_archive 'CCDC 2306224'
loop_
_audit_author_name
_audit_author_address
liu
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2022-06-29
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N8 O7, H2 O'
_chemical_formula_sum            'C6 H6 N8 O8'
_chemical_formula_weight         318.19
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.7948(4)
_cell_length_b                   9.4387(5)
_cell_length_c                   16.5829(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.635(6)
_cell_angle_gamma                90
_cell_volume                     1062.40(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1792
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.6770
_cell_measurement_theta_min      5.3960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4736
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.404
_diffrn_reflns_theta_min         5.341
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  12.00   0.50    0.50    --   42.30 -57.00  30.00  112
  2  ω     84.00 131.00   0.50    0.50    --   42.30  77.00 -60.00   94
  3  ω     35.00  60.00   0.50    0.50    --   42.30 -57.00  90.00   50
  4  ω    -43.00   9.00   0.50    0.50    --   42.30 -57.00  90.00  104
  5  ω     15.00  73.00   0.50    0.50    --   42.30 -57.00  30.00  116
  6  ω    105.00 130.00   0.50    0.50    --   42.30  77.00 -30.00   50
  7  ω    151.00 183.00   0.50    0.80    --  101.60  82.00 -60.00   64
  8  ω     13.00  65.00   0.50    0.80    --  101.60 -63.00  30.00  104
  9  ω    134.00 170.00   0.50    0.80    --  101.60  38.00 -30.00   72
 10  ω     69.00 127.00   0.50    0.80    --  101.60  38.00 -30.00  116
 11  ω     69.00 109.00   0.50    0.80    --  101.60 -63.00  30.00   80
 12  ω     12.00 118.00   0.50    0.80    --  101.60 -50.00-150.00  212
 13  ω     12.00 143.00   0.50    0.80    --  101.60 -82.00  30.00  262
 14  ω     52.00 172.00   0.50    0.80    --  101.60 -25.00   0.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1470794000
_diffrn_orient_matrix_UB_12      -0.0012000000
_diffrn_orient_matrix_UB_13      0.0680013000
_diffrn_orient_matrix_UB_21      0.0483467000
_diffrn_orient_matrix_UB_22      -0.1570010000
_diffrn_orient_matrix_UB_23      0.0168752000
_diffrn_orient_matrix_UB_31      0.1659626000
_diffrn_orient_matrix_UB_32      0.0446841000
_diffrn_orient_matrix_UB_33      0.0611338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1682
_reflns_number_total             2027
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.7146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1141
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O8(H8A)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), N8(H8)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.3489(3) 0.11061(19) 0.48633(15) 0.0474(6) Uani 1 1 d . . . . .
O2 O 1.1287(2) -0.01716(17) 0.42471(11) 0.0252(4) Uani 1 1 d . . . . .
O3 O 1.3354(2) 0.38498(16) 0.47451(10) 0.0211(4) Uani 1 1 d . . . . .
O4 O 0.9111(2) 0.75976(16) 0.37911(11) 0.0237(4) Uani 1 1 d . . . . .
O5 O 0.6240(2) 0.77826(17) 0.31656(10) 0.0228(4) Uani 1 1 d . . . . .
O6 O 0.1215(2) 0.53166(18) 0.22207(11) 0.0264(4) Uani 1 1 d . . . . .
O7 O 0.2677(2) 0.32953(18) 0.25161(11) 0.0257(4) Uani 1 1 d . . . . .
N1 N 1.1964(3) 0.10080(19) 0.44575(12) 0.0210(4) Uani 1 1 d . . . . .
N2 N 0.7971(3) 0.09315(19) 0.36799(11) 0.0191(4) Uani 1 1 d . . . . .
H2A H 0.681548 0.099041 0.344841 0.023 Uiso 1 1 calc R U . . .
H2B H 0.846378 0.011541 0.380138 0.023 Uiso 1 1 calc R U . . .
N3 N 0.8068(3) 0.33427(19) 0.36295(11) 0.0169(4) Uani 1 1 d . . . . .
N4 N 0.6190(3) 0.3370(2) 0.32603(11) 0.0180(4) Uani 1 1 d . . . . .
N5 N 0.4155(3) 0.5334(2) 0.28178(12) 0.0198(4) Uani 1 1 d . . . . .
H5 H 0.408334 0.624327 0.280658 0.024 Uiso 1 1 calc R U . . .
N6 N 0.2584(3) 0.4587(2) 0.24937(12) 0.0194(4) Uani 1 1 d . . . . .
N7 N 0.7609(3) 0.7071(2) 0.34704(11) 0.0180(4) Uani 1 1 d . . . . .
N8 N 1.0672(3) 0.47819(19) 0.41138(11) 0.0168(4) Uani 1 1 d . . . . .
H8 H 1.116954 0.561546 0.417137 0.020 Uiso 1 1 calc R U . . .
C1 C 1.1776(3) 0.3612(2) 0.43948(14) 0.0165(4) Uani 1 1 d . . . . .
C2 C 1.0878(3) 0.2237(2) 0.42191(14) 0.0179(5) Uani 1 1 d . . . . .
C3 C 0.8984(3) 0.2087(2) 0.38479(13) 0.0173(5) Uani 1 1 d . . . . .
C4 C 0.8868(3) 0.4649(2) 0.37587(13) 0.0158(4) Uani 1 1 d . . . . .
C5 C 0.7460(3) 0.5588(2) 0.34558(13) 0.0170(5) Uani 1 1 d . . . . .
C6 C 0.5852(3) 0.4734(2) 0.31620(13) 0.0164(5) Uani 1 1 d . . . . .
O8 O 1.2960(2) 0.70452(18) 0.45540(11) 0.0257(4) Uani 1 1 d G . . . .
H8A H 1.411764 0.695415 0.476408 0.039 Uiso 1 1 d G U . . .
H8B H 1.279(4) 0.784(3) 0.4479(16) 0.020(7) 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 1.213(3) . ?
O2 N1 1.248(3) . ?
O3 C1 1.217(3) . ?
O4 N7 1.234(2) . ?
O5 N7 1.237(2) . ?
O6 N6 1.227(2) . ?
O7 N6 1.221(3) . ?
N1 C2 1.421(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C3 1.313(3) . ?
N3 N4 1.390(2) . ?
N3 C3 1.379(3) . ?
N3 C4 1.360(3) . ?
N4 C6 1.316(3) . ?
N5 H5 0.8600 . ?
N5 N6 1.369(3) . ?
N5 C6 1.383(3) . ?
N7 C5 1.403(3) . ?
N8 H8 0.8600 . ?
N8 C1 1.403(3) . ?
N8 C4 1.341(3) . ?
C1 C2 1.458(3) . ?
C2 C3 1.408(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.426(3) . ?
O8 H8A 0.8500 . ?
O8 H8B 0.77(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
O1 N1 O2 121.17(19) . . ?
O1 N1 C2 120.76(19) . . ?
O2 N1 C2 118.07(18) . . ?
H2A N2 H2B 120.0 . . ?
C3 N2 H2A 120.0 . . ?
C3 N2 H2B 120.0 . . ?
C3 N3 N4 121.72(18) . . ?
C4 N3 N4 113.86(17) . . ?
C4 N3 C3 124.42(18) . . ?
C6 N4 N3 102.97(17) . . ?
N6 N5 H5 117.6 . . ?
N6 N5 C6 124.85(18) . . ?
C6 N5 H5 117.6 . . ?
O6 N6 N5 114.87(18) . . ?
O7 N6 O6 127.50(19) . . ?
O7 N6 N5 117.62(18) . . ?
O4 N7 O5 123.30(19) . . ?
O4 N7 C5 117.86(18) . . ?
O5 N7 C5 118.83(18) . . ?
C1 N8 H8 118.8 . . ?
C4 N8 H8 118.8 . . ?
C4 N8 C1 122.42(18) . . ?
O3 C1 N8 117.36(19) . . ?
O3 C1 C2 127.7(2) . . ?
N8 C1 C2 114.95(19) . . ?
N1 C2 C1 117.64(19) . . ?
C3 C2 N1 119.46(19) . . ?
C3 C2 C1 122.87(19) . . ?
N2 C3 N3 115.63(19) . . ?
N2 C3 C2 129.5(2) . . ?
N3 C3 C2 114.87(19) . . ?
N3 C4 C5 105.04(18) . . ?
N8 C4 N3 120.31(19) . . ?
N8 C4 C5 134.6(2) . . ?
N7 C5 C6 128.6(2) . . ?
C4 C5 N7 125.8(2) . . ?
C4 C5 C6 105.55(19) . . ?
N4 C6 N5 126.06(19) . . ?
N4 C6 C5 112.58(19) . . ?
N5 C6 C5 121.36(19) . . ?
H8A O8 H8B 107.1 . . ?

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
O1 N1 C2 C1 7.2(3) . . . . ?
O1 N1 C2 C3 -171.1(2) . . . . ?
O2 N1 C2 C1 -173.8(2) . . . . ?
O2 N1 C2 C3 7.9(3) . . . . ?
O3 C1 C2 N1 -2.0(4) . . . . ?
O3 C1 C2 C3 176.3(2) . . . . ?
O4 N7 C5 C4 -1.2(3) . . . . ?
O4 N7 C5 C6 176.5(2) . . . . ?
O5 N7 C5 C4 179.0(2) . . . . ?
O5 N7 C5 C6 -3.4(3) . . . . ?
N1 C2 C3 N2 0.8(4) . . . . ?
N1 C2 C3 N3 -179.09(19) . . . . ?
N3 N4 C6 N5 -179.8(2) . . . . ?
N3 N4 C6 C5 0.1(2) . . . . ?
N3 C4 C5 N7 178.5(2) . . . . ?
N3 C4 C5 C6 0.5(2) . . . . ?
N4 N3 C3 N2 0.4(3) . . . . ?
N4 N3 C3 C2 -179.70(19) . . . . ?
N4 N3 C4 N8 179.71(19) . . . . ?
N4 N3 C4 C5 -0.4(2) . . . . ?
N6 N5 C6 N4 -2.8(4) . . . . ?
N6 N5 C6 C5 177.3(2) . . . . ?
N7 C5 C6 N4 -178.4(2) . . . . ?
N7 C5 C6 N5 1.5(4) . . . . ?
N8 C1 C2 N1 177.34(19) . . . . ?
N8 C1 C2 C3 -4.4(3) . . . . ?
N8 C4 C5 N7 -1.6(4) . . . . ?
N8 C4 C5 C6 -179.7(2) . . . . ?
C1 N8 C4 N3 -2.6(3) . . . . ?
C1 N8 C4 C5 177.6(2) . . . . ?
C1 C2 C3 N2 -177.4(2) . . . . ?
C1 C2 C3 N3 2.7(3) . . . . ?
C3 N3 N4 C6 179.31(19) . . . . ?
C3 N3 C4 N8 0.6(3) . . . . ?
C3 N3 C4 C5 -179.5(2) . . . . ?
C4 N3 N4 C6 0.2(2) . . . . ?
C4 N3 C3 N2 179.4(2) . . . . ?
C4 N3 C3 C2 -0.7(3) . . . . ?
C4 N8 C1 O3 -176.3(2) . . . . ?
C4 N8 C1 C2 4.3(3) . . . . ?
C4 C5 C6 N4 -0.4(3) . . . . ?
C4 C5 C6 N5 179.5(2) . . . . ?
C6 N5 N6 O6 179.7(2) . . . . ?
C6 N5 N6 O7 0.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.612
####################################################################### 
# 
# 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_2023-1
_database_code_depnum_ccdc_archive 'CCDC 2306223'
loop_
_audit_author_name
_audit_author_address
liu
;sichuan university of science and engineering
China
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2023-05-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N6 O4, H2 O'
_chemical_formula_sum            'C6 H6 N6 O5'
_chemical_formula_weight         242.17
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.2185(4)
_cell_length_b                   17.8398(10)
_cell_length_c                   16.5515(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.761(6)
_cell_angle_gamma                90
_cell_volume                     1819.35(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3201
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      28.0540
_cell_measurement_theta_min      2.4880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8087
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  77.00   1.00    3.00    --   11.90-178.00-120.00   26
  2  ω    -45.00  40.00   1.00    3.00    --   11.90 -57.00-120.00   85
  3  ω     -5.00  81.00   1.00    3.00    --   11.90  38.00  60.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0642542000
_diffrn_orient_matrix_UB_12      -0.0004621000
_diffrn_orient_matrix_UB_13      -0.0388216000
_diffrn_orient_matrix_UB_21      -0.0254504000
_diffrn_orient_matrix_UB_22      0.0384285000
_diffrn_orient_matrix_UB_23      0.0045244000
_diffrn_orient_matrix_UB_31      0.0920341000
_diffrn_orient_matrix_UB_32      0.0103035000
_diffrn_orient_matrix_UB_33      -0.0184839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2657
_reflns_number_total             3207
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+0.6911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H) groups, All O(H,H) groups
2.a Free rotating group:
 O11(H11A,H11B), O12(H12C,H12D)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C10(H10)
2.c Idealised tetrahedral OH refined as rotating group:
 N8(H8A), N12(H12A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.2609(2) 0.78099(7) 0.79295(9) 0.0273(4) Uani 1 1 d . . . . .
O2 O 0.2518(2) 0.72334(8) 0.67736(9) 0.0293(4) Uani 1 1 d . . . . .
O4 O 0.2306(3) 0.35806(8) 0.99657(9) 0.0368(4) Uani 1 1 d . . . . .
O5 O 0.2469(2) 0.47217(8) 1.04302(9) 0.0314(4) Uani 1 1 d . . . . .
N1 N 0.2554(2) 0.72268(9) 0.75244(11) 0.0209(4) Uani 1 1 d . . . . .
N2 N 0.2601(3) 0.59328(9) 0.92391(10) 0.0226(4) Uani 1 1 d . . . . .
N3 N 0.2397(2) 0.52325(8) 0.79911(9) 0.0169(4) Uani 1 1 d . . . . .
N4 N 0.2270(2) 0.45047(9) 0.77021(10) 0.0190(4) Uani 1 1 d . . . . .
N5 N 0.2394(3) 0.42640(9) 0.98671(10) 0.0226(4) Uani 1 1 d . . . . .
N8 N 0.2310(3) 0.57269(10) 0.67038(10) 0.0227(4) Uani 1 1 d . . . . .
H8A H 0.241927 0.613742 0.646417 0.034 Uiso 1 1 calc R U . . .
H8B H 0.226(3) 0.5248(13) 0.6520(15) 0.035(7) Uiso 1 1 d . . . . .
C1 C 0.2625(3) 0.65329(11) 0.87818(13) 0.0227(5) Uani 1 1 d . . . . .
H1 H 0.270983 0.700615 0.904721 0.027 Uiso 1 1 calc R U . . .
C2 C 0.2533(3) 0.65278(10) 0.79289(11) 0.0181(4) Uani 1 1 d . . . . .
C3 C 0.2412(3) 0.58439(10) 0.74883(12) 0.0176(4) Uani 1 1 d . . . . .
C4 C 0.2475(3) 0.52788(10) 0.88306(11) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.2399(3) 0.45337(11) 0.90681(12) 0.0182(4) Uani 1 1 d . . . . .
C6 C 0.2274(3) 0.40971(11) 0.83636(12) 0.0194(4) Uani 1 1 d . . . . .
H6 H 0.219923 0.356525 0.836243 0.023 Uiso 1 1 calc R U . . .
O6 O -0.2250(3) 0.22169(9) 0.97270(9) 0.0350(4) Uani 1 1 d . . . . .
O7 O -0.2356(3) 0.15735(8) 0.86118(10) 0.0369(4) Uani 1 1 d . . . . .
O9 O -0.3287(3) 0.44094(8) 0.51663(9) 0.0386(4) Uani 1 1 d . . . . .
O10 O -0.2399(2) 0.32927(8) 0.48328(9) 0.0344(4) Uani 1 1 d . . . . .
N6 N -0.2709(2) 0.40952(9) 0.82635(10) 0.0207(4) Uani 1 1 d . . . . .
N7 N -0.2718(2) 0.36905(8) 0.75530(10) 0.0173(4) Uani 1 1 d . . . . .
N9 N -0.2360(3) 0.21749(9) 0.89762(10) 0.0243(4) Uani 1 1 d . . . . .
N10 N -0.2595(3) 0.24305(9) 0.70590(10) 0.0214(4) Uani 1 1 d . . . . .
N11 N -0.2836(3) 0.37496(10) 0.53392(10) 0.0242(4) Uani 1 1 d . . . . .
N12 N -0.2946(3) 0.47611(9) 0.67621(12) 0.0239(4) Uani 1 1 d . . . . .
H12A H -0.275979 0.494011 0.723578 0.036 Uiso 1 1 calc R U . . .
H12B H -0.308(3) 0.4941(13) 0.6262(15) 0.035(7) Uiso 1 1 d . . . . .
C7 C -0.2578(3) 0.35799(11) 0.88370(12) 0.0208(4) Uani 1 1 d . . . . .
H7 H -0.254166 0.368799 0.940074 0.025 Uiso 1 1 calc R U . . .
C8 C -0.2499(3) 0.28513(11) 0.85196(12) 0.0192(4) Uani 1 1 d . . . . .
C9 C -0.2595(3) 0.29215(10) 0.76795(12) 0.0172(4) Uani 1 1 d . . . . .
C10 C -0.2689(3) 0.27362(11) 0.63284(12) 0.0210(4) Uani 1 1 d . . . . .
H10 H -0.266276 0.240764 0.587808 0.025 Uiso 1 1 calc R U . . .
C11 C -0.2822(3) 0.35017(11) 0.61656(12) 0.0201(4) Uani 1 1 d . . . . .
C12 C -0.2844(3) 0.40288(10) 0.68014(12) 0.0178(4) Uani 1 1 d . . . . .
O11 O 0.1843(3) 0.42118(9) 0.58921(11) 0.0474(5) Uani 1 1 d G . . . .
H11A H 0.216805 0.387977 0.625660 0.071 Uiso 1 1 d G U . . .
H11B H 0.217437 0.401467 0.545780 0.071 Uiso 1 1 d G U . . .
O12 O -0.2487(3) 0.58091(8) 0.79624(9) 0.0299(4) Uani 1 1 d G . . . .
H12C H -0.240557 0.572536 0.847127 0.045 Uiso 1 1 d G U . . .
H12D H -0.242921 0.628364 0.792484 0.045 Uiso 1 1 d G 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
O1 N1 1.236(2) . ?
O2 N1 1.240(2) . ?
O4 N5 1.232(2) . ?
O5 N5 1.235(2) . ?
N1 C2 1.416(2) . ?
N2 C1 1.312(3) . ?
N2 C4 1.345(2) . ?
N3 N4 1.382(2) . ?
N3 C3 1.373(2) . ?
N3 C4 1.386(2) . ?
N4 C6 1.314(3) . ?
N5 C5 1.408(2) . ?
N8 H8A 0.8400 . ?
N8 H8B 0.91(2) . ?
N8 C3 1.308(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.405(3) . ?
C2 C3 1.418(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.396(3) . ?
C6 H6 0.9500 . ?
O6 N9 1.237(2) . ?
O7 N9 1.231(2) . ?
O9 N11 1.235(2) . ?
O10 N11 1.226(2) . ?
N6 N7 1.379(2) . ?
N6 C7 1.316(3) . ?
N7 C9 1.388(2) . ?
N7 C12 1.375(2) . ?
N9 C8 1.420(3) . ?
N10 C9 1.350(2) . ?
N10 C10 1.321(3) . ?
N11 C11 1.436(3) . ?
N12 H12A 0.8400 . ?
N12 H12B 0.88(2) . ?
N12 C12 1.309(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.405(3) . ?
C8 C9 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(3) . ?
C11 C12 1.413(3) . ?
O11 H11A 0.8502 . ?
O11 H11B 0.8501 . ?
O12 H12C 0.8501 . ?
O12 H12D 0.8500 . ?

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
O1 N1 O2 122.10(16) . . ?
O1 N1 C2 119.09(17) . . ?
O2 N1 C2 118.81(16) . . ?
C1 N2 C4 114.95(17) . . ?
N4 N3 C4 113.29(15) . . ?
C3 N3 N4 122.77(15) . . ?
C3 N3 C4 123.93(16) . . ?
C6 N4 N3 103.76(15) . . ?
O4 N5 O5 123.50(17) . . ?
O4 N5 C5 117.93(17) . . ?
O5 N5 C5 118.56(16) . . ?
H8A N8 H8B 131.6 . . ?
C3 N8 H8A 109.5 . . ?
C3 N8 H8B 118.7(15) . . ?
N2 C1 H1 117.5 . . ?
N2 C1 C2 124.91(18) . . ?
C2 C1 H1 117.5 . . ?
N1 C2 C3 121.18(17) . . ?
C1 C2 N1 117.88(17) . . ?
C1 C2 C3 120.94(17) . . ?
N3 C3 C2 112.10(17) . . ?
N8 C3 N3 118.14(17) . . ?
N8 C3 C2 129.77(18) . . ?
N2 C4 N3 123.17(17) . . ?
N2 C4 C5 133.61(18) . . ?
N3 C4 C5 103.22(16) . . ?
C4 C5 N5 126.69(17) . . ?
C4 C5 C6 107.33(17) . . ?
C6 C5 N5 125.96(18) . . ?
N4 C6 C5 112.39(17) . . ?
N4 C6 H6 123.8 . . ?
C5 C6 H6 123.8 . . ?
C7 N6 N7 104.01(15) . . ?
N6 N7 C9 113.26(15) . . ?
C12 N7 N6 122.32(15) . . ?
C12 N7 C9 124.41(16) . . ?
O6 N9 C8 118.30(16) . . ?
O7 N9 O6 122.77(17) . . ?
O7 N9 C8 118.93(17) . . ?
C10 N10 C9 115.10(17) . . ?
O9 N11 C11 119.09(16) . . ?
O10 N11 O9 122.68(17) . . ?
O10 N11 C11 118.23(17) . . ?
H12A N12 H12B 136.2 . . ?
C12 N12 H12A 109.5 . . ?
C12 N12 H12B 114.1(15) . . ?
N6 C7 H7 123.9 . . ?
N6 C7 C8 112.23(18) . . ?
C8 C7 H7 123.9 . . ?
C7 C8 N9 126.12(18) . . ?
C9 C8 N9 126.91(17) . . ?
C9 C8 C7 106.97(17) . . ?
N10 C9 N7 122.15(18) . . ?
N10 C9 C8 134.31(18) . . ?
C8 C9 N7 103.53(16) . . ?
N10 C10 H10 117.4 . . ?
N10 C10 C11 125.19(19) . . ?
C11 C10 H10 117.4 . . ?
C10 C11 N11 118.61(17) . . ?
C10 C11 C12 121.00(18) . . ?
C12 C11 N11 120.33(17) . . ?
N7 C12 C11 112.13(16) . . ?
N12 C12 N7 118.64(18) . . ?
N12 C12 C11 129.23(19) . . ?
H11A O11 H11B 104.5 . . ?
H12C O12 H12D 104.5 . . ?

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
O1 N1 C2 C1 -1.4(3) . . . . ?
O1 N1 C2 C3 178.28(16) . . . . ?
O2 N1 C2 C1 178.61(16) . . . . ?
O2 N1 C2 C3 -1.7(3) . . . . ?
O4 N5 C5 C4 179.52(18) . . . . ?
O4 N5 C5 C6 1.3(3) . . . . ?
O5 N5 C5 C4 -0.2(3) . . . . ?
O5 N5 C5 C6 -178.49(18) . . . . ?
N1 C2 C3 N3 -179.59(15) . . . . ?
N1 C2 C3 N8 0.1(3) . . . . ?
N2 C1 C2 N1 179.42(17) . . . . ?
N2 C1 C2 C3 -0.2(3) . . . . ?
N2 C4 C5 N5 1.5(3) . . . . ?
N2 C4 C5 C6 180.0(2) . . . . ?
N3 N4 C6 C5 0.0(2) . . . . ?
N3 C4 C5 N5 -178.77(17) . . . . ?
N3 C4 C5 C6 -0.25(19) . . . . ?
N4 N3 C3 N8 -0.3(3) . . . . ?
N4 N3 C3 C2 179.47(15) . . . . ?
N4 N3 C4 N2 -179.96(16) . . . . ?
N4 N3 C4 C5 0.3(2) . . . . ?
N5 C5 C6 N4 178.71(17) . . . . ?
C1 N2 C4 N3 0.6(3) . . . . ?
C1 N2 C4 C5 -179.7(2) . . . . ?
C1 C2 C3 N3 0.1(2) . . . . ?
C1 C2 C3 N8 179.79(19) . . . . ?
C3 N3 N4 C6 -179.26(16) . . . . ?
C3 N3 C4 N2 -0.9(3) . . . . ?
C3 N3 C4 C5 179.35(16) . . . . ?
C4 N2 C1 C2 -0.1(3) . . . . ?
C4 N3 N4 C6 -0.16(19) . . . . ?
C4 N3 C3 N8 -179.31(16) . . . . ?
C4 N3 C3 C2 0.5(2) . . . . ?
C4 C5 C6 N4 0.2(2) . . . . ?
O6 N9 C8 C7 -1.7(3) . . . . ?
O6 N9 C8 C9 178.75(17) . . . . ?
O7 N9 C8 C7 178.29(18) . . . . ?
O7 N9 C8 C9 -1.3(3) . . . . ?
O9 N11 C11 C10 168.93(18) . . . . ?
O9 N11 C11 C12 -13.9(3) . . . . ?
O10 N11 C11 C10 -11.0(3) . . . . ?
O10 N11 C11 C12 166.21(17) . . . . ?
N6 N7 C9 N10 179.63(15) . . . . ?
N6 N7 C9 C8 -0.16(19) . . . . ?
N6 N7 C12 N12 0.4(3) . . . . ?
N6 N7 C12 C11 179.86(15) . . . . ?
N6 C7 C8 N9 -179.84(17) . . . . ?
N6 C7 C8 C9 -0.2(2) . . . . ?
N7 N6 C7 C8 0.1(2) . . . . ?
N9 C8 C9 N7 179.85(17) . . . . ?
N9 C8 C9 N10 0.1(3) . . . . ?
N10 C10 C11 N11 177.87(17) . . . . ?
N10 C10 C11 C12 0.7(3) . . . . ?
N11 C11 C12 N7 -177.02(15) . . . . ?
N11 C11 C12 N12 2.4(3) . . . . ?
C7 N6 N7 C9 0.05(19) . . . . ?
C7 N6 N7 C12 179.90(15) . . . . ?
C7 C8 C9 N7 0.20(19) . . . . ?
C7 C8 C9 N10 -179.55(19) . . . . ?
C9 N7 C12 N12 -179.78(17) . . . . ?
C9 N7 C12 C11 -0.3(2) . . . . ?
C9 N10 C10 C11 -1.2(3) . . . . ?
C10 N10 C9 N7 0.9(2) . . . . ?
C10 N10 C9 C8 -179.3(2) . . . . ?
C10 C11 C12 N7 0.1(2) . . . . ?
C10 C11 C12 N12 179.49(19) . . . . ?
C12 N7 C9 N10 -0.2(3) . . . . ?
C12 N7 C9 C8 179.99(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.452
_oxdiff_exptl_absorpt_empirical_full_min 0.597
