# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_AKS_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2269135'
loop_
_audit_author_name
_audit_author_address
'Subhamoy Biswas'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2023-10-18 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         ?
_chemical_formula_sum            'C12 H12 N4 O2'
_chemical_formula_weight         244.26

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   10.0470(8)
_cell_length_b                   4.9832(4)
_cell_length_c                   11.8477(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.242(2)
_cell_angle_gamma                90
_cell_volume                     574.94(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            18229
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_full        24.988
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2013
_reflns_number_gt                1867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.3040P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(8)
_chemical_absolute_configuration S
_refine_ls_number_reflns         2013
_refine_ls_number_parameters     171
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   0.715
_refine_ls_restrained_S_all      0.715
_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 0.3039(2) 0.6994(5) 0.42548(18) 0.0491(6) Uani 1 1 d . . . . .
O2 O 0.0381(4) 0.7124(9) 0.4677(4) 0.0855(11) Uani 1 1 d . . . . .
N1 N 0.5497(3) 0.5046(5) 0.1805(2) 0.0357(6) Uani 1 1 d . . . . .
N2 N 0.5757(3) 0.3297(6) 0.1018(2) 0.0468(7) Uani 1 1 d . . . . .
N3 N 0.7069(3) 0.2673(7) 0.1375(3) 0.0564(8) Uani 1 1 d . . . . .
N4 N 0.4126(2) 0.7480(5) 0.27825(19) 0.0352(6) Uani 1 1 d . . . . .
C1 C 0.7609(4) 0.4038(9) 0.2365(3) 0.0558(10) Uani 1 1 d . . . . .
H1 H 0.852176 0.394679 0.278440 0.067 Uiso 1 1 calc R U . . .
C2 C 0.6626(3) 0.5565(7) 0.2660(3) 0.0405(7) Uani 1 1 d . . . . .
C3 C 0.6582(3) 0.7370(8) 0.3662(3) 0.0471(8) Uani 1 1 d . . . . .
H3A H 0.738744 0.851448 0.383403 0.057 Uiso 1 1 calc R U . . .
H3B H 0.659446 0.629389 0.434639 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5292(3) 0.9101(6) 0.3376(3) 0.0433(8) Uani 1 1 d . . . . .
H4A H 0.512556 0.983121 0.408770 0.052 Uiso 1 1 calc R U . . .
H4B H 0.541441 1.058533 0.288178 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4130(3) 0.6266(6) 0.1669(2) 0.0346(7) Uani 1 1 d . . . . .
H5 H 0.394822 0.760706 0.104547 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3190(3) 0.6370(6) 0.3291(3) 0.0359(7) Uani 1 1 d . . . . .
C7 C 0.2434(3) 0.4342(7) 0.2467(3) 0.0366(7) Uani 1 1 d . . . . .
C8 C 0.2981(3) 0.4262(6) 0.1501(3) 0.0367(7) Uani 1 1 d . . . . .
C9 C 0.1362(3) 0.2675(8) 0.2557(3) 0.0476(8) Uani 1 1 d . . . . .
H9 H 0.100457 0.271551 0.321075 0.057 Uiso 1 1 calc R U . . .
C10 C 0.0841(3) 0.0952(8) 0.1642(4) 0.0575(10) Uani 1 1 d . . . . .
H10 H 0.012100 -0.019117 0.167715 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1382(4) 0.0906(8) 0.0670(3) 0.0552(9) Uani 1 1 d . . . . .
H11 H 0.101217 -0.026897 0.006427 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2451(3) 0.2555(8) 0.0581(3) 0.0445(8) Uani 1 1 d . . . . .
H12 H 0.280395 0.252156 -0.007465 0.053 Uiso 1 1 calc R U . . .
H13A H 0.112(6) 0.715(14) 0.452(4) 0.085(16) Uiso 1 1 d . . . . .
H13B H 0.007(6) 0.867(14) 0.474(5) 0.09(2) 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 C6 1.228(3) . ?
N1 C2 1.347(4) . ?
N1 N2 1.348(4) . ?
N1 C5 1.474(4) . ?
N2 N3 1.318(4) . ?
N3 C1 1.349(5) . ?
N4 C6 1.355(4) . ?
N4 C5 1.452(4) . ?
N4 C4 1.453(4) . ?
C1 C2 1.359(5) . ?
C2 C3 1.498(5) . ?
C3 C4 1.524(5) . ?
C5 C8 1.502(4) . ?
C6 C7 1.478(4) . ?
C7 C9 1.386(5) . ?
C7 C8 1.387(4) . ?
C8 C12 1.382(5) . ?
C9 C10 1.381(6) . ?
C10 C11 1.389(6) . ?
C11 C12 1.377(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
C2 N1 N2 111.9(3) . . ?
C2 N1 C5 126.4(3) . . ?
N2 N1 C5 121.6(2) . . ?
N3 N2 N1 106.2(3) . . ?
N2 N3 C1 108.5(3) . . ?
C6 N4 C5 113.0(3) . . ?
C6 N4 C4 125.2(3) . . ?
C5 N4 C4 119.3(2) . . ?
N3 C1 C2 110.1(3) . . ?
N1 C2 C1 103.3(3) . . ?
N1 C2 C3 121.8(3) . . ?
C1 C2 C3 134.8(3) . . ?
C2 C3 C4 110.7(3) . . ?
N4 C4 C3 109.5(3) . . ?
N4 C5 N1 106.4(2) . . ?
N4 C5 C8 103.0(2) . . ?
N1 C5 C8 113.9(2) . . ?
O1 C6 N4 124.6(3) . . ?
O1 C6 C7 128.8(3) . . ?
N4 C6 C7 106.6(2) . . ?
C9 C7 C8 121.3(3) . . ?
C9 C7 C6 129.9(3) . . ?
C8 C7 C6 108.8(3) . . ?
C12 C8 C7 121.0(3) . . ?
C12 C8 C5 130.4(3) . . ?
C7 C8 C5 108.6(3) . . ?
C10 C9 C7 117.6(3) . . ?
C9 C10 C11 120.8(3) . . ?
C12 C11 C10 121.7(3) . . ?
C11 C12 C8 117.6(3) . . ?

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.030

