# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_pm-cb-197-b_auto
_database_code_depnum_ccdc_archive 'CCDC 2484476'
loop_
_audit_author_name
_audit_author_address
'Chidananda Biswal'
;National Institute of Science Education and Research, Bhubaneswar
India
;
_audit_update_record             
;
2025-09-02 deposited with the CCDC.	2026-05-18 downloaded from the CCDC.
;
_audit_creation_date             2025-09-02
_audit_creation_method           
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Br N2 O2'
_chemical_formula_sum            'C15 H10 Br N2 O2'
_chemical_formula_weight         330.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Br'
_chemical_oxdiff_usercomment     'Colorless niddle'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.4693(6)
_cell_length_b                   10.4315(11)
_cell_length_c                   16.4870(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.938(9)
_cell_angle_gamma                90
_cell_volume                     1265.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4139
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.5850
_cell_measurement_theta_min      3.7690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12707
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.516
_diffrn_reflns_theta_min         3.389
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  64.00   0.50    4.50    --   -0.86-154.00 -66.00   52
  2  ω     33.00  58.00   0.50    4.50    --   -1.72-154.00 -66.00   50
  3  ω    -23.00  21.00   0.50    4.50    --   -0.86  77.00  30.00   88
  4  ω    -24.00  21.00   0.50    4.50    --   -0.86  77.00 120.00   90
  5  ω    -24.00  21.00   0.50    4.50    --   -0.86  77.00  90.00   90
  6  ω    -22.00  13.00   0.50    4.50    --   -1.72  77.00   0.00   70
  7  ω    -17.00  22.00   0.50    4.50    --   -1.72 -77.00  90.00   78
  8  ω    -11.00  30.00   0.50    4.50    --   -1.72 -99.00   0.00   82
  9  ω    -33.00   2.00   0.50    4.50    --   -1.72 -37.00-120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0209155000
_diffrn_orient_matrix_UB_12      0.0493881000
_diffrn_orient_matrix_UB_13      -0.0296877000
_diffrn_orient_matrix_UB_21      0.0183750000
_diffrn_orient_matrix_UB_22      0.0466646000
_diffrn_orient_matrix_UB_23      0.0316373000
_diffrn_orient_matrix_UB_31      0.0923343000
_diffrn_orient_matrix_UB_32      0.0019593000
_diffrn_orient_matrix_UB_33      -0.0051112000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2143
_reflns_number_total             2894
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.321
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.5367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C17(H17), C6(H6), C16(H16), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br18 Br 0.16263(4) 0.65142(4) 0.49535(2) 0.02181(15) Uani 1 1 d . . . . .
O20 O 0.8368(3) 0.2775(3) 0.79992(17) 0.0199(6) Uani 1 1 d . . . . .
O19 O 1.1081(3) 0.4455(3) 0.78436(18) 0.0254(7) Uani 1 1 d . . . . .
N4 N 0.9133(4) 0.5640(3) 0.6937(2) 0.0173(7) Uani 1 1 d . . . . .
N1 N 0.6317(4) 0.4025(3) 0.7168(2) 0.0158(7) Uani 1 1 d . . . . .
C9 C 0.4235(4) 0.5240(4) 0.6134(2) 0.0144(8) Uani 1 1 d . . . . .
H9 H 0.3244 0.4708 0.6207 0.017 Uiso 1 1 calc R U . . .
C5 C 0.7400(4) 0.5839(4) 0.6483(2) 0.0150(8) Uani 1 1 d . . . . .
C7 C 0.5396(5) 0.7028(4) 0.5445(2) 0.0183(8) Uani 1 1 d . . . . .
H7 H 0.5194 0.7691 0.5044 0.022 Uiso 1 1 calc R U . . .
C17 C 0.2346(5) 0.2042(4) 0.6431(2) 0.0185(8) Uani 1 1 d . . . . .
H17 H 0.1488 0.2651 0.6556 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7105(5) 0.6838(4) 0.5910(2) 0.0187(8) Uani 1 1 d . . . . .
H6 H 0.8080 0.7388 0.5840 0.022 Uiso 1 1 calc R U . . .
C3 C 0.9565(4) 0.4634(4) 0.7456(2) 0.0173(8) Uani 1 1 d . . . . .
C8 C 0.3995(5) 0.6235(4) 0.5573(2) 0.0173(8) Uani 1 1 d . . . . .
C2 C 0.8029(5) 0.3716(4) 0.7557(2) 0.0166(8) Uani 1 1 d . . . . .
C10 C 0.5963(4) 0.5034(4) 0.6590(2) 0.0169(8) Uani 1 1 d . . . . .
C16 C 0.1758(5) 0.1011(4) 0.5910(2) 0.0218(9) Uani 1 1 d . . . . .
H16 H 0.0504 0.0916 0.5689 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5418(5) 0.1294(4) 0.6559(2) 0.0169(8) Uani 1 1 d . . . . .
H13 H 0.6676 0.1389 0.6773 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4177(4) 0.2185(4) 0.6768(2) 0.0141(8) Uani 1 1 d . . . . .
C11 C 0.4806(4) 0.3244(4) 0.7375(2) 0.0144(8) Uani 1 1 d . . . . .
H11A H 0.3764 0.3816 0.7408 0.017 Uiso 1 1 calc R U . . .
H11B H 0.5195 0.2859 0.7926 0.017 Uiso 1 1 calc R U . . .
C14 C 0.4835(5) 0.0274(4) 0.6044(2) 0.0202(8) Uani 1 1 d . . . . .
H14 H 0.5694 -0.0330 0.5912 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3007(5) 0.0127(4) 0.5717(3) 0.0238(9) Uani 1 1 d . . . . .
H15 H 0.2613 -0.0574 0.5363 0.029 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
Br18 C8 1.907(3) . ?
O20 C2 1.223(5) . ?
O19 C3 1.215(4) . ?
N4 C5 1.395(4) . ?
N4 C3 1.358(5) . ?
N1 C2 1.366(4) . ?
N1 C10 1.414(5) . ?
N1 C11 1.478(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.381(5) . ?
C9 C10 1.394(5) . ?
C5 C6 1.398(6) . ?
C5 C10 1.398(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.386(5) . ?
C7 C8 1.378(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.399(6) . ?
C17 C12 1.392(5) . ?
C6 H6 0.9500 . ?
C3 C2 1.526(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.387(6) . ?
C13 H13 0.9500 . ?
C13 C12 1.397(5) . ?
C13 C14 1.385(5) . ?
C12 C11 1.510(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C14 H14 0.9500 . ?
C14 C15 1.387(5) . ?
C15 H15 0.9500 . ?

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
C3 N4 C5 123.4(3) . . ?
C2 N1 C10 122.9(3) . . ?
C2 N1 C11 116.9(3) . . ?
C10 N1 C11 120.3(3) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
N4 C5 C6 119.8(3) . . ?
N4 C5 C10 120.3(3) . . ?
C6 C5 C10 119.9(3) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C8 C7 C6 118.7(4) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C12 C17 C16 120.6(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
O19 C3 N4 123.3(3) . . ?
O19 C3 C2 119.8(4) . . ?
N4 C3 C2 116.9(3) . . ?
C9 C8 Br18 118.3(3) . . ?
C7 C8 Br18 119.0(3) . . ?
C7 C8 C9 122.6(3) . . ?
O20 C2 N1 123.4(3) . . ?
O20 C2 C3 119.1(3) . . ?
N1 C2 C3 117.5(3) . . ?
C9 C10 N1 121.8(3) . . ?
C9 C10 C5 119.9(4) . . ?
C5 C10 N1 118.3(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C14 C13 C12 120.7(3) . . ?
C17 C12 C13 118.6(3) . . ?
C17 C12 C11 121.0(3) . . ?
C13 C12 C11 120.4(3) . . ?
N1 C11 C12 114.4(3) . . ?
N1 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?

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
O19 C3 C2 O20 -3.4(6) . . . . ?
O19 C3 C2 N1 174.0(3) . . . . ?
N4 C5 C6 C7 178.7(3) . . . . ?
N4 C5 C10 N1 0.2(5) . . . . ?
N4 C5 C10 C9 -180.0(3) . . . . ?
N4 C3 C2 O20 177.8(3) . . . . ?
N4 C3 C2 N1 -4.9(5) . . . . ?
C5 N4 C3 O19 179.1(4) . . . . ?
C5 N4 C3 C2 -2.1(5) . . . . ?
C17 C16 C15 C14 0.0(6) . . . . ?
C17 C12 C11 N1 -128.9(4) . . . . ?
C6 C5 C10 N1 179.3(3) . . . . ?
C6 C5 C10 C9 -0.9(6) . . . . ?
C6 C7 C8 Br18 178.5(3) . . . . ?
C6 C7 C8 C9 -1.6(6) . . . . ?
C3 N4 C5 C6 -174.6(4) . . . . ?
C3 N4 C5 C10 4.5(6) . . . . ?
C8 C9 C10 N1 -179.2(3) . . . . ?
C8 C9 C10 C5 1.0(6) . . . . ?
C8 C7 C6 C5 1.6(6) . . . . ?
C2 N1 C10 C9 172.6(4) . . . . ?
C2 N1 C10 C5 -7.5(5) . . . . ?
C2 N1 C11 C12 -97.8(4) . . . . ?
C10 N1 C2 O20 -173.1(4) . . . . ?
C10 N1 C2 C3 9.7(5) . . . . ?
C10 N1 C11 C12 81.9(4) . . . . ?
C10 C9 C8 Br18 -179.8(3) . . . . ?
C10 C9 C8 C7 0.3(6) . . . . ?
C10 C5 C6 C7 -0.4(6) . . . . ?
C16 C17 C12 C13 1.5(6) . . . . ?
C16 C17 C12 C11 -175.9(4) . . . . ?
C13 C12 C11 N1 53.7(4) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C12 C17 C16 C15 -0.8(6) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C11 N1 C2 O20 6.6(6) . . . . ?
C11 N1 C2 C3 -170.6(3) . . . . ?
C11 N1 C10 C9 -7.0(5) . . . . ?
C11 N1 C10 C5 172.8(3) . . . . ?
C14 C13 C12 C17 -1.5(6) . . . . ?
C14 C13 C12 C11 175.9(3) . . . . ?

_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 1.883
_oxdiff_exptl_absorpt_empirical_full_min 0.723
