# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_SR
_audit_block_doi                 10.5517/ccdc.csd.cc2lw1xg
_database_code_depnum_ccdc_archive 'CCDC 2409286'
loop_
_audit_author_name
_audit_author_address
'Subburethinam Ramesh'
;University
India
;
_audit_update_record             
;
2024-12-11 deposited with the CCDC.	2025-03-27 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         'C10 H7 Br N4 O'
_chemical_formula_sum            'C10 H7 Br N4 O'
_chemical_formula_weight         279.11

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'
Br Br -0.2901 2.4595 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.7279(5)
_cell_length_b                   11.0272(5)
_cell_length_c                   7.6786(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.347(4)
_cell_angle_gamma                90
_cell_volume                     1073.03(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3986
_cell_measurement_theta_min      3.2010
_cell_measurement_theta_max      26.0370

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.814
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10867
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1876
_reflns_number_gt                1458
_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       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0367P)²+0.6944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1876
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.16828(3) 0.60878(4) 0.74765(5) 0.06538(19) Uani 1 1 d . . . . .
O1 O 0.65456(17) 0.7580(2) 0.4631(3) 0.0516(6) Uani 1 1 d . . . . .
N2 N 0.63532(18) 0.5938(2) 0.6476(3) 0.0345(6) Uani 1 1 d . . . . .
N3 N 0.69267(19) 0.6721(2) 0.5577(3) 0.0370(6) Uani 1 1 d . . . . .
N1 N 0.6981(2) 0.5106(2) 0.7348(3) 0.0394(6) Uani 1 1 d . . . . .
C6 C 0.5248(2) 0.6010(2) 0.6651(4) 0.0332(7) Uani 1 1 d . . . . .
C9 C 0.7945(2) 0.6358(3) 0.5890(4) 0.0390(7) Uani 1 1 d . . . . .
C8 C 0.7952(2) 0.5356(3) 0.6996(4) 0.0404(7) Uani 1 1 d . . . . .
C3 C 0.3136(2) 0.6045(3) 0.7123(4) 0.0403(8) Uani 1 1 d . . . . .
C1 C 0.4607(2) 0.6893(3) 0.5841(4) 0.0447(8) Uani 1 1 d . . . . .
H1 H 0.488552 0.747432 0.513628 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3768(3) 0.5150(3) 0.7913(4) 0.0470(8) Uani 1 1 d . . . . .
H4 H 0.348317 0.456030 0.859575 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4833(3) 0.5141(3) 0.7678(4) 0.0434(8) Uani 1 1 d . . . . .
H5 H 0.526922 0.454697 0.821547 0.052 Uiso 1 1 calc R U . . .
C2 C 0.3542(3) 0.6902(3) 0.6091(4) 0.0485(8) Uani 1 1 d . . . . .
H2 H 0.310260 0.749368 0.555390 0.058 Uiso 1 1 calc R U . . .
N4 N 0.9414(3) 0.7499(3) 0.4521(5) 0.0730(10) Uani 1 1 d . . . . .
C10 C 0.8759(3) 0.6995(3) 0.5125(5) 0.0493(8) Uani 1 1 d . . . . .
C11 C 0.8889(3) 0.4622(3) 0.7698(5) 0.0586(10) Uani 1 1 d . . . . .
H11A H 0.866526 0.400286 0.846260 0.088 Uiso 1 1 calc R U . . .
H11B H 0.939313 0.514038 0.833720 0.088 Uiso 1 1 calc R U . . .
H11C H 0.920683 0.425101 0.674561 0.088 Uiso 1 1 calc R 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
Br1 C3 1.895(3) . ?
O1 N3 1.263(3) . ?
N2 N1 1.352(3) . ?
N2 N3 1.360(3) . ?
N2 C6 1.427(4) . ?
N3 C9 1.357(4) . ?
N1 C8 1.319(4) . ?
C6 C5 1.378(4) . ?
C6 C1 1.381(4) . ?
C9 C8 1.393(4) . ?
C9 C10 1.423(5) . ?
C8 C11 1.499(5) . ?
C3 C2 1.366(5) . ?
C3 C4 1.377(5) . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
N4 C10 1.136(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
N1 N2 N3 111.2(2) . . ?
N1 N2 C6 122.2(2) . . ?
N3 N2 C6 126.3(2) . . ?
O1 N3 C9 129.3(2) . . ?
O1 N3 N2 125.0(2) . . ?
C9 N3 N2 105.8(2) . . ?
C8 N1 N2 106.2(2) . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 N2 116.7(3) . . ?
C1 C6 N2 122.9(3) . . ?
N3 C9 C8 107.1(3) . . ?
N3 C9 C10 120.1(3) . . ?
C8 C9 C10 132.8(3) . . ?
N1 C8 C9 109.8(3) . . ?
N1 C8 C11 122.8(3) . . ?
C9 C8 C11 127.4(3) . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 Br1 119.5(2) . . ?
C4 C3 Br1 119.5(2) . . ?
C6 C1 C2 119.2(3) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
N4 C10 C9 179.5(4) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
N1 N2 N3 O1 179.0(2) . . . . ?
C6 N2 N3 O1 -6.4(4) . . . . ?
N1 N2 N3 C9 0.5(3) . . . . ?
C6 N2 N3 C9 175.1(3) . . . . ?
N3 N2 N1 C8 -0.3(3) . . . . ?
C6 N2 N1 C8 -175.2(3) . . . . ?
N1 N2 C6 C5 -3.7(4) . . . . ?
N3 N2 C6 C5 -177.7(3) . . . . ?
N1 N2 C6 C1 176.6(3) . . . . ?
N3 N2 C6 C1 2.5(4) . . . . ?
O1 N3 C9 C8 -178.9(3) . . . . ?
N2 N3 C9 C8 -0.4(3) . . . . ?
O1 N3 C9 C10 1.4(5) . . . . ?
N2 N3 C9 C10 179.9(3) . . . . ?
N2 N1 C8 C9 0.0(3) . . . . ?
N2 N1 C8 C11 -179.0(3) . . . . ?
N3 C9 C8 N1 0.3(4) . . . . ?
C10 C9 C8 N1 179.9(3) . . . . ?
N3 C9 C8 C11 179.2(3) . . . . ?
C10 C9 C8 C11 -1.1(6) . . . . ?
C5 C6 C1 C2 0.7(5) . . . . ?
N2 C6 C1 C2 -179.5(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
Br1 C3 C4 C5 -178.6(2) . . . . ?
C1 C6 C5 C4 -0.3(5) . . . . ?
N2 C6 C5 C4 179.9(3) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C3 C2 C1 -0.9(5) . . . . ?
Br1 C3 C2 C1 179.0(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.055

