# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_22019261GH2_0m
_database_code_depnum_ccdc_archive 'CCDC 2032203'
loop_
_audit_author_name
_audit_author_address
'Hao Gu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 N11 O4, 3(H2 O)'
_chemical_formula_sum            'C6 H9 N11 O7'
_chemical_formula_weight         347.24

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                   28.555(5)
_cell_length_b                   4.9529(8)
_cell_length_c                   21.680(4)
_cell_angle_alpha                90
_cell_angle_beta                 118.805(5)
_cell_angle_gamma                90
_cell_volume                     2686.8(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1785
_cell_measurement_theta_max      24.694
_cell_measurement_theta_min      2.917

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5706
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0968 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.7656. The λ/2 correction factor is Not present.
;
_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12282
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         25.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2483
_reflns_number_gt                1603
_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       'SAINT V8.38A (?, 2016)'
_computing_cell_refinement       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0768P)²+4.1351P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2483
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O7 O 0.43321(11) 1.3667(6) 0.70716(15) 0.0298(7) Uani 1 1 d . . . . .
O4 O 0.38385(10) -0.1044(6) 0.39710(15) 0.0299(7) Uani 1 1 d G . . . .
H4A H 0.391785 -0.242650 0.379122 0.045 Uiso 1 1 d G U . . .
H4B H 0.350082 -0.110097 0.385230 0.045 Uiso 1 1 d G U . . .
O6 O 0.34672(11) 1.3816(6) 0.66206(15) 0.0346(8) Uani 1 1 d . . . . .
O3 O 0.28026(11) -0.0056(7) 0.37270(17) 0.0397(8) Uani 1 1 d G . . . .
H3A H 0.271917 -0.161670 0.383100 0.060 Uiso 1 1 d G U . . .
H3B H 0.258070 0.015448 0.328077 0.060 Uiso 1 1 d G U . . .
O2 O 0.68977(11) 0.5506(7) 0.72259(16) 0.0402(8) Uani 1 1 d . . . . .
O5 O 0.27146(10) 0.4921(6) 0.43752(17) 0.0376(8) Uani 1 1 d G . . . .
H5A H 0.241774 0.474904 0.439123 0.056 Uiso 1 1 d G U . . .
H5B H 0.278524 0.341805 0.422847 0.056 Uiso 1 1 d G U . . .
O1 O 0.69018(11) 0.9059(6) 0.78085(16) 0.0400(8) Uani 1 1 d . . . . .
N3 N 0.53299(11) 0.8212(6) 0.67628(16) 0.0213(7) Uani 1 1 d . . . . .
H3 H 0.504449 0.898311 0.674048 0.026 Uiso 1 1 calc R U . . .
N10 N 0.42549(11) 0.9324(6) 0.62658(16) 0.0210(7) Uani 1 1 d . . . . .
N4 N 0.58160(11) 0.5425(6) 0.65296(16) 0.0217(7) Uani 1 1 d . . . . .
N7 N 0.40085(12) 0.3707(6) 0.50514(17) 0.0234(8) Uani 1 1 d . . . . .
N5 N 0.48747(12) 0.2790(6) 0.54554(16) 0.0234(8) Uani 1 1 d . . . . .
N6 N 0.43697(12) 0.2204(6) 0.50056(16) 0.0229(8) Uani 1 1 d . . . . .
H6 H 0.428206 0.089135 0.469596 0.027 Uiso 1 1 calc R U . . .
N1 N 0.66796(12) 0.7273(7) 0.73845(18) 0.0273(8) Uani 1 1 d . . . . .
N2 N 0.58374(12) 0.8953(6) 0.72065(16) 0.0236(8) Uani 1 1 d . . . . .
N9 N 0.33581(12) 0.9625(7) 0.57737(17) 0.0271(8) Uani 1 1 d . . . . .
N11 N 0.38796(13) 1.2834(7) 0.66783(18) 0.0259(8) Uani 1 1 d . . . . .
N8 N 0.34958(11) 0.7628(7) 0.54787(17) 0.0252(8) Uani 1 1 d . . . . .
H8 H 0.326773 0.657506 0.514018 0.030 Uiso 1 1 calc R U . . .
C1 C 0.60969(14) 0.7221(8) 0.70355(19) 0.0208(9) Uani 1 1 d . . . . .
C2 C 0.53207(14) 0.6144(8) 0.6362(2) 0.0219(9) Uani 1 1 d . . . . .
C4 C 0.42955(14) 0.5462(8) 0.55667(19) 0.0213(9) Uani 1 1 d . . . . .
C5 C 0.40287(14) 0.7447(8) 0.57686(19) 0.0216(9) Uani 1 1 d . . . . .
C6 C 0.38324(14) 1.0560(8) 0.6244(2) 0.0225(9) Uani 1 1 d . . . . .
C3 C 0.48403(14) 0.4869(8) 0.5816(2) 0.0203(9) Uani 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
O7 N11 1.227(4) . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8704 . ?
O6 N11 1.224(4) . ?
O3 H3A 0.8700 . ?
O3 H3B 0.8704 . ?
O2 N1 1.216(4) . ?
O5 H5A 0.8691 . ?
O5 H5B 0.8704 . ?
O1 N1 1.212(4) . ?
N3 C2 1.336(5) . ?
N3 N2 1.348(4) . ?
N3 H3 0.8800 . ?
N10 C5 1.331(5) . ?
N10 C6 1.334(5) . ?
N4 C2 1.328(5) . ?
N4 C1 1.338(5) . ?
N7 N6 1.314(4) . ?
N7 C4 1.339(5) . ?
N5 C3 1.325(5) . ?
N5 N6 1.327(4) . ?
N6 H6 0.8800 . ?
N1 C1 1.459(5) . ?
N2 C1 1.299(5) . ?
N9 C6 1.326(5) . ?
N9 N8 1.336(5) . ?
N11 C6 1.432(5) . ?
N8 C5 1.341(4) . ?
N8 H8 0.8800 . ?
C2 C3 1.454(5) . ?
C4 C3 1.410(5) . ?
C4 C5 1.435(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
H4A O4 H4B 109.4 . . ?
H3A O3 H3B 104.5 . . ?
H5A O5 H5B 109.5 . . ?
C2 N3 N2 110.5(3) . . ?
C2 N3 H3 124.7 . . ?
N2 N3 H3 124.7 . . ?
C5 N10 C6 102.4(3) . . ?
C2 N4 C1 100.7(3) . . ?
N6 N7 C4 104.1(3) . . ?
C3 N5 N6 103.9(3) . . ?
N7 N6 N5 115.8(3) . . ?
N7 N6 H6 122.1 . . ?
N5 N6 H6 122.1 . . ?
O1 N1 O2 126.0(3) . . ?
O1 N1 C1 117.1(3) . . ?
O2 N1 C1 116.9(3) . . ?
C1 N2 N3 100.5(3) . . ?
C6 N9 N8 101.5(3) . . ?
O6 N11 O7 125.2(4) . . ?
O6 N11 C6 117.7(3) . . ?
O7 N11 C6 117.1(3) . . ?
N9 N8 C5 110.8(3) . . ?
N9 N8 H8 124.6 . . ?
C5 N8 H8 124.6 . . ?
N2 C1 N4 118.3(3) . . ?
N2 C1 N1 120.4(3) . . ?
N4 C1 N1 121.4(3) . . ?
N4 C2 N3 110.0(3) . . ?
N4 C2 C3 124.7(3) . . ?
N3 C2 C3 125.2(3) . . ?
N7 C4 C3 107.7(3) . . ?
N7 C4 C5 119.8(3) . . ?
C3 C4 C5 132.5(3) . . ?
N10 C5 N8 109.3(3) . . ?
N10 C5 C4 127.1(3) . . ?
N8 C5 C4 123.5(3) . . ?
N9 C6 N10 116.0(4) . . ?
N9 C6 N11 121.2(3) . . ?
N10 C6 N11 122.7(3) . . ?
N5 C3 C4 108.5(3) . . ?
N5 C3 C2 120.5(3) . . ?
C4 C3 C2 131.0(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4B O3 0.87 1.95 2.786(4) 161.1 . yes
O4 H4A N4 0.87 1.94 2.809(4) 173.1 5_656 yes
N3 H3 N10 0.88 1.98 2.775(4) 148.9 . yes
N6 H6 O4 0.88 1.75 2.577(4) 154.8 . yes
N8 H8 O5 0.88 1.84 2.712(4) 169.6 . yes

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.080

