# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_exp_1386_HCQ
_database_code_depnum_ccdc_archive 'CCDC 2270859'
loop_
_audit_author_name
_audit_author_address
SAVITA
;BITS
India
;
_audit_update_record             
;
2023-06-19 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2023-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C9 H5 N3 O3, H2 O'
_chemical_formula_sum            'C9 H7 N3 O4'
_chemical_formula_weight         221.17
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   16.4937(3)
_cell_length_b                   8.07760(10)
_cell_length_c                   14.6807(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.189(2)
_cell_angle_gamma                90
_cell_volume                     1868.54(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3321
_cell_measurement_temperature    93
_cell_measurement_theta_max      78.7020
_cell_measurement_theta_min      6.1380
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5723
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             915.6344
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4615
_diffrn_reflns_theta_full        79.5663
_diffrn_reflns_theta_max         79.57
_diffrn_reflns_theta_min         5.62
_diffrn_ambient_temperature      93
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9593
_diffrn_measured_fraction_theta_max 0.9593
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00  88.00   0.50    1.37    --    0.00  57.00  60.00   84
  2  ω    -16.00  10.00   0.50    1.37    --    0.00  57.00 -90.00   52
  3  ω    -17.00  49.00   0.50    1.37    --    0.00  37.00-120.00  132
  4  ω     31.00  88.00   0.50    1.37    --    0.00  57.00 -90.00  114
  5  ω     26.00 137.00   0.50    5.47    --  107.20 -77.00-150.00  222
  6  ω     24.00 108.00   0.50    5.47    --  107.20 -30.00 -30.00  168
  7  ω     45.00 126.00   0.50    5.47    --  107.20 -30.00-150.00  162
  8  ω    100.00 139.00   0.50    5.47    --  107.20 -82.00  60.00   78
  9  ω     90.00 129.00   0.50    5.47    --  107.20 -15.00  60.00   78
 10  ω     28.00  90.00   0.50    5.47    --  107.20 -15.00-150.00  124
 11  ω     94.00 121.00   0.50    5.47    --  107.20 -15.00-150.00   54
 12  ω     69.00 130.00   0.50    5.47    --  107.20 -77.00   0.00  122
 13  ω     24.00  49.00   0.50    5.47    --  107.20 -77.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0853960000
_diffrn_orient_matrix_UB_12      0.0432784000
_diffrn_orient_matrix_UB_13      0.0167677000
_diffrn_orient_matrix_UB_21      -0.0403451000
_diffrn_orient_matrix_UB_22      0.0232628000
_diffrn_orient_matrix_UB_23      -0.1080943000
_diffrn_orient_matrix_UB_31      -0.0251900000
_diffrn_orient_matrix_UB_32      -0.1843823000
_diffrn_orient_matrix_UB_33      -0.0097321000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1797
_reflns_number_total             1954
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.6374
_refine_diff_density_min         -0.7283
_refine_diff_density_rms         0.0610
_refine_ls_d_res_high            0.7839
_refine_ls_d_res_low             7.8785
_refine_ls_goodness_of_fit_ref   1.0268
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    13
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.0268
_refine_ls_shift/su_max          0.0256
_refine_ls_shift/su_mean         0.0009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0914P)²+1.4438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1401
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O002(H00a,H00b)
2.b Aromatic/amide H refined with riding coordinates:
 C1C(H1C), C2C(H2C), C3C(H3C), C4C(H4C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1O(H1O)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1O O 0.45030(7) 0.59327(13) 0.57464(8) 0.0287(3) Uani 1.000000 .
H1O H 0.4355(13) 0.6224(8) 0.6223(10) 0.0431(4) Uiso 1.000000 GR
O002 O 0.39290(7) 0.61439(13) 0.72070(8) 0.0294(3) Uani 1.000000 .
H00a H 0.4180(9) 0.5393(18) 0.7594(12) 0.0441(4) Uiso 1.000000 G
H00b H 0.33956(17) 0.605(2) 0.7098(14) 0.0441(4) Uiso 1.000000 G
O2O O 0.36304(7) -0.04317(14) 0.47966(8) 0.0326(3) Uani 1.000000 .
O3O O 0.54451(7) 0.33993(14) 0.66891(7) 0.0299(3) Uani 1.000000 .
N1N N 0.42731(8) 0.43034(15) 0.55272(8) 0.0235(3) Uani 1.000000 .
N2N N 0.38341(8) 0.10563(15) 0.50156(8) 0.0241(3) Uani 1.000000 .
N3N N 0.54282(9) -0.09358(17) 0.66894(9) 0.0314(3) Uani 1.000000 .
C1C C 0.30645(10) 0.52925(19) 0.42594(11) 0.0286(3) Uani 1.000000 .
H1C H 0.32061(10) 0.64118(19) 0.44342(11) 0.0343(4) Uiso 1.000000 R
C2C C 0.23626(10) 0.4913(2) 0.35038(11) 0.0329(4) Uani 1.000000 .
H2C H 0.20210(10) 0.5786(2) 0.31592(11) 0.0395(5) Uiso 1.000000 R
C3C C 0.21413(10) 0.3273(2) 0.32325(11) 0.0341(4) Uani 1.000000 .
H3C H 0.16576(10) 0.3046(2) 0.27063(11) 0.0409(5) Uiso 1.000000 R
C4C C 0.26233(9) 0.1990(2) 0.37268(10) 0.0296(4) Uani 1.000000 .
H4C H 0.24748(9) 0.0874(2) 0.35497(10) 0.0355(4) Uiso 1.000000 R
C5C C 0.45257(9) 0.14358(18) 0.57414(10) 0.0239(3) Uani 1.000000 .
C6C C 0.48010(9) 0.31160(18) 0.60332(10) 0.0234(3) Uani 1.000000 .
C7C C 0.35635(9) 0.39976(19) 0.47632(10) 0.0235(3) Uani 1.000000 .
C8C C 0.33351(9) 0.23556(19) 0.44939(10) 0.0243(3) Uani 1.000000 .
C9C C 0.50165(9) 0.00980(18) 0.62544(10) 0.0258(3) Uani 1.000000 .


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
O1O H1O 0.8400 . ?
O1O N1N 1.3810(16) . ?
O002 H00a 0.8500 . ?
O002 H00b 0.8501 . ?
O2O N2N 1.2638(16) . ?
O3O C6C 1.2263(18) . ?
N1N C6C 1.3592(19) . ?
N1N C7C 1.3831(18) . ?
N2N C5C 1.3462(19) . ?
N2N C8C 1.4117(19) . ?
N3N C9C 1.145(2) . ?
C1C H1C 0.9500 . ?
C1C C2C 1.381(2) . ?
C1C C7C 1.400(2) . ?
C2C H2C 0.9500 . ?
C2C C3C 1.400(3) . ?
C3C H3C 0.9500 . ?
C3C C4C 1.375(2) . ?
C4C H4C 0.9500 . ?
C4C C8C 1.3972(19) . ?
C5C C6C 1.455(2) . ?
C5C C9C 1.425(2) . ?
C7C C8C 1.403(2) . ?

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
N1N O1O H1O 109.5 . . ?
H00b O002 H00a 109.5 . . ?
C6C N1N O1O 117.24(11) . . ?
C7C N1N O1O 117.87(12) . . ?
C7C N1N C6C 124.68(12) . . ?
C5C N2N O2O 121.15(13) . . ?
C8C N2N O2O 120.04(12) . . ?
C8C N2N C5C 118.81(12) . . ?
C2C C1C H1C 120.62(10) . . ?
C7C C1C H1C 120.62(9) . . ?
C7C C1C C2C 118.77(15) . . ?
H2C C2C C1C 119.17(10) . . ?
C3C C2C C1C 121.66(15) . . ?
C3C C2C H2C 119.17(9) . . ?
H3C C3C C2C 119.96(9) . . ?
C4C C3C C2C 120.09(14) . . ?
C4C C3C H3C 119.96(9) . . ?
H4C C4C C3C 120.56(9) . . ?
C8C C4C C3C 118.88(15) . . ?
C8C C4C H4C 120.56(10) . . ?
C6C C5C N2N 124.28(13) . . ?
C9C C5C N2N 117.51(13) . . ?
C9C C5C C6C 118.21(13) . . ?
N1N C6C O3O 124.32(13) . . ?
C5C C6C O3O 121.87(13) . . ?
C5C C6C N1N 113.80(12) . . ?
C1C C7C N1N 121.31(14) . . ?
C8C C7C N1N 119.32(13) . . ?
C8C C7C C1C 119.37(13) . . ?
C4C C8C N2N 119.76(14) . . ?
C7C C8C N2N 119.00(12) . . ?
C7C C8C C4C 121.24(14) . . ?
C5C C9C N3N 177.52(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 2.055
_oxdiff_exptl_absorpt_empirical_full_min 0.740
