# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2299474'
loop_
_audit_author_name
_audit_author_address
'ANUP CHOUDHURY'
;Tezpur University
India
;
_audit_update_record             
;
2023-10-05 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N O4'
_chemical_formula_weight         233.22

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.45(2)
_cell_length_b                   33.45(2)
_cell_length_c                   5.541(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5369(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    997
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      13.62

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             2196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5267
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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            51845
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_av_R_equivalents  0.2469
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.655
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2342
_reflns_number_gt                1481
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1377P)²+6.2532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2342
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2473
_refine_ls_wR_factor_gt          0.2172
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.17584(12) 0.08729(15) 0.2707(7) 0.0789(14) Uani 1 1 d . . . . .
O2 O 0.20036(9) 0.05849(10) 0.5540(5) 0.0420(8) Uani 1 1 d . . . . .
O3 O 0.28031(9) 0.16673(8) -0.3181(4) 0.0310(7) Uani 1 1 d . . . . .
O4 O 0.21905(9) 0.14815(9) -0.0838(5) 0.0370(8) Uani 1 1 d . . . . .
N1 N 0.31064(11) 0.12363(10) -0.0235(6) 0.0264(8) Uani 1 1 d . . . . .
C1 C 0.35685(14) 0.09122(13) 0.1567(6) 0.0296(9) Uani 1 1 d . . . . .
H1 H 0.380425 0.103555 0.042873 0.035 Uiso 1 1 calc R U . . .
C2 C 0.35715(13) 0.06488(12) 0.3457(7) 0.0314(9) Uani 1 1 d . . . . .
H2 H 0.381382 0.058910 0.359929 0.038 Uiso 1 1 calc R U . . .
C3 C 0.32164(13) 0.04675(13) 0.5179(6) 0.0302(9) Uani 1 1 d . . . . .
H3 H 0.323308 0.029524 0.645212 0.036 Uiso 1 1 calc R U . . .
C4 C 0.28442(13) 0.05360(12) 0.5047(6) 0.0288(9) Uani 1 1 d . . . . .
H4 H 0.261116 0.041114 0.619979 0.035 Uiso 1 1 calc R U . . .
C5 C 0.28257(13) 0.08023(12) 0.3104(6) 0.0267(9) Uani 1 1 d . . . . .
C6 C 0.31915(13) 0.09859(12) 0.1441(6) 0.0264(9) Uani 1 1 d . . . . .
C7 C 0.25047(13) 0.09474(12) 0.2343(6) 0.0271(9) Uani 1 1 d . . . . .
C8 C 0.26983(12) 0.12176(12) 0.0275(6) 0.0254(8) Uani 1 1 d . . . . .
C9 C 0.20578(14) 0.08179(14) 0.3465(6) 0.0325(9) Uani 1 1 d . . . . .
C10 C 0.20500(15) 0.17192(15) -0.2499(8) 0.0440(11) Uani 1 1 d . . . . .
H10A H 0.177187 0.170369 -0.192482 0.066 Uiso 1 1 calc R U . . .
H10B H 0.228936 0.203631 -0.262206 0.066 Uiso 1 1 calc R U . . .
H10C H 0.199521 0.157599 -0.405860 0.066 Uiso 1 1 calc R U . . .
C11 C 0.15625(14) 0.04061(15) 0.6724(8) 0.0457(12) Uani 1 1 d . . . . .
H11A H 0.156003 0.024743 0.817210 0.069 Uiso 1 1 calc R U . . .
H11B H 0.151168 0.065647 0.712277 0.069 Uiso 1 1 calc R U . . .
H11C H 0.132221 0.019535 0.566292 0.069 Uiso 1 1 calc R U . . .
C12 C 0.25720(12) 0.14763(12) -0.1416(6) 0.0268(9) Uani 1 1 d . . . . .
H11 H 0.3294(17) 0.1380(15) -0.157(8) 0.053(13) 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 C9 1.182(5) . ?
O2 C9 1.350(4) . ?
O2 C11 1.443(5) . ?
O3 C12 1.212(4) . ?
O4 C12 1.324(4) . ?
O4 C10 1.440(5) . ?
N1 C8 1.364(5) . ?
N1 C6 1.372(4) . ?
C1 C2 1.372(5) . ?
C1 C6 1.403(5) . ?
C2 C3 1.403(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.418(5) . ?
C5 C6 1.404(5) . ?
C5 C7 1.445(5) . ?
C7 C8 1.401(5) . ?
C7 C9 1.470(5) . ?
C8 C12 1.474(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
C9 O2 C11 116.2(3) . . ?
C12 O4 C10 115.8(3) . . ?
C8 N1 C6 109.9(3) . . ?
C2 C1 C6 116.6(4) . . ?
C1 C2 C3 121.3(4) . . ?
C4 C3 C2 122.2(3) . . ?
C3 C4 C5 118.2(4) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 C7 107.0(3) . . ?
C4 C5 C7 134.9(3) . . ?
N1 C6 C1 128.3(3) . . ?
N1 C6 C5 108.0(3) . . ?
C1 C6 C5 123.6(3) . . ?
C8 C7 C5 105.9(3) . . ?
C8 C7 C9 127.6(3) . . ?
C5 C7 C9 126.5(3) . . ?
N1 C8 C7 109.2(3) . . ?
N1 C8 C12 114.5(3) . . ?
C7 C8 C12 136.3(3) . . ?
O1 C9 O2 120.9(4) . . ?
O1 C9 C7 128.3(4) . . ?
O2 C9 C7 110.7(3) . . ?
O3 C12 O4 123.6(3) . . ?
O3 C12 C8 121.9(3) . . ?
O4 C12 C8 114.5(3) . . ?

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
C6 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C3 C4 C5 C7 179.8(4) . . . . ?
C8 N1 C6 C1 179.3(3) . . . . ?
C8 N1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 N1 179.5(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C4 C5 C6 N1 -178.7(3) . . . . ?
C7 C5 C6 N1 0.8(4) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C7 C5 C6 C1 -179.0(3) . . . . ?
C6 C5 C7 C8 -0.9(4) . . . . ?
C4 C5 C7 C8 178.6(4) . . . . ?
C6 C5 C7 C9 176.7(3) . . . . ?
C4 C5 C7 C9 -3.9(6) . . . . ?
C6 N1 C8 C7 -0.1(4) . . . . ?
C6 N1 C8 C12 179.9(3) . . . . ?
C5 C7 C8 N1 0.6(4) . . . . ?
C9 C7 C8 N1 -176.9(3) . . . . ?
C5 C7 C8 C12 -179.4(4) . . . . ?
C9 C7 C8 C12 3.1(7) . . . . ?
C11 O2 C9 O1 0.8(6) . . . . ?
C11 O2 C9 C7 -175.3(3) . . . . ?
C8 C7 C9 O1 9.0(7) . . . . ?
C5 C7 C9 O1 -168.0(4) . . . . ?
C8 C7 C9 O2 -175.2(3) . . . . ?
C5 C7 C9 O2 7.8(5) . . . . ?
C10 O4 C12 O3 2.0(5) . . . . ?
C10 O4 C12 C8 -178.1(3) . . . . ?
N1 C8 C12 O3 3.8(5) . . . . ?
C7 C8 C12 O3 -176.2(4) . . . . ?
N1 C8 C12 O4 -176.1(3) . . . . ?
C7 C8 C12 O4 3.9(6) . . . . ?

_refine_diff_density_max         0.754
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.098

