# 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. 
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data_ac_sylyl_2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2522737'
loop_
_audit_author_name
_audit_author_address
'Pallav Jyoti Arandhara'
;Indian Institute of Technology, Guwahati
India
;
_audit_update_record             
;
2026-01-14 deposited with the CCDC.	2026-03-23 downloaded from the CCDC.
;
_audit_creation_date             2026-01-10
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Br N'
_chemical_formula_sum            'C15 H10 Br N'
_chemical_formula_weight         284.15
_chemical_melting_point          ?
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'

_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                   13.5714(14)
_cell_length_b                   14.8390(16)
_cell_length_c                   5.9416(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.035(3)
_cell_angle_gamma                90
_cell_volume                     1194.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6872
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.22
_cell_measurement_theta_min      2.75
_shelx_estimated_absorpt_T_max   0.471
_shelx_estimated_absorpt_T_min   0.408
_exptl_absorpt_coefficient_mu    3.414
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.5000
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15793
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         2.035
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1148
_reflns_number_total             2433
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         1.223
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.799
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1784
_refine_ls_R_factor_gt           0.1019
_refine_ls_restrained_S_all      1.799
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2841
_refine_ls_wR_factor_ref         0.3256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br1 Br 0.15309(8) 0.61668(8) 0.1051(2) 0.1101(7) Uani 1 1 d . . . . .
N1 N 0.6437(5) 0.5994(4) 0.4129(11) 0.0671(17) Uani 1 1 d . . . . .
C1 C 0.7383(7) 0.6046(5) 0.4932(14) 0.072(2) Uani 1 1 d . . . . .
C2 C 0.7679(7) 0.6433(5) 0.7089(15) 0.074(2) Uani 1 1 d . . . . .
C3 C 0.8675(9) 0.6525(6) 0.7729(19) 0.095(3) Uani 1 1 d . . . . .
H3 H 0.886201 0.676631 0.913181 0.114 Uiso 1 1 calc R U . . .
C4 C 0.9372(7) 0.6267(6) 0.6319(19) 0.091(3) Uani 1 1 d . . . . .
H4 H 1.003535 0.635504 0.673813 0.109 Uiso 1 1 calc R U . . .
C5 C 0.9108(7) 0.5864(6) 0.4220(18) 0.091(3) Uani 1 1 d . . . . .
H5 H 0.959762 0.567292 0.329179 0.110 Uiso 1 1 calc R U . . .
C6 C 0.8096(7) 0.5749(6) 0.3516(15) 0.086(2) Uani 1 1 d . . . . .
H6 H 0.791773 0.548188 0.213868 0.103 Uiso 1 1 calc R U . . .
C7 C 0.5736(7) 0.6272(4) 0.5396(14) 0.067(2) Uani 1 1 d . . . . .
C8 C 0.5960(7) 0.6621(5) 0.7579(13) 0.075(2) Uani 1 1 d . . . . .
H8 H 0.545049 0.679624 0.846958 0.090 Uiso 1 1 calc R U . . .
C9 C 0.6906(7) 0.6703(5) 0.8388(13) 0.080(2) Uani 1 1 d . . . . .
H9 H 0.704124 0.694028 0.981935 0.096 Uiso 1 1 calc R U . . .
C10 C 0.4708(6) 0.6230(4) 0.4455(14) 0.063(2) Uani 1 1 d . . . . .
C11 C 0.4506(6) 0.5818(5) 0.2372(13) 0.072(2) Uani 1 1 d . . . . .
H11 H 0.502170 0.555985 0.162815 0.086 Uiso 1 1 calc R U . . .
C12 C 0.3567(7) 0.5782(5) 0.1384(14) 0.077(2) Uani 1 1 d . . . . .
H12 H 0.345690 0.549006 0.000838 0.093 Uiso 1 1 calc R U . . .
C13 C 0.2803(7) 0.6167(5) 0.2391(16) 0.073(2) Uani 1 1 d . . . . .
C14 C 0.2997(7) 0.6595(6) 0.4473(16) 0.087(3) Uani 1 1 d . . . . .
H14 H 0.248192 0.686516 0.519451 0.104 Uiso 1 1 calc R U . . .
C15 C 0.3920(7) 0.6620(5) 0.5448(15) 0.075(2) Uani 1 1 d . . . . .
H15 H 0.402450 0.690856 0.682906 0.090 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 C13 1.863(10) . ?
N1 C1 1.348(11) . ?
N1 C7 1.311(10) . ?
C1 C2 1.442(12) . ?
C1 C6 1.387(11) . ?
C2 C3 1.392(13) . ?
C2 C9 1.394(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.352(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.412(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.425(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.415(11) . ?
C7 C10 1.477(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.352(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(11) . ?
C10 C15 1.376(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.351(11) . ?
C13 C14 1.402(13) . ?
C14 H14 0.9300 . ?
C14 C15 1.353(12) . ?
C15 H15 0.9300 . ?

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
C7 N1 C1 119.1(7) . . ?
N1 C1 C2 123.5(8) . . ?
N1 C1 C6 116.7(7) . . ?
C6 C1 C2 119.7(9) . . ?
C3 C2 C1 120.2(9) . . ?
C3 C2 C9 124.7(9) . . ?
C9 C2 C1 115.1(8) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(9) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(9) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(9) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.5(9) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N1 C7 C8 121.0(8) . . ?
N1 C7 C10 118.0(7) . . ?
C8 C7 C10 121.0(8) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(8) . . ?
C9 C8 H8 119.6 . . ?
C2 C9 H9 119.8 . . ?
C8 C9 C2 120.4(7) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C7 119.5(7) . . ?
C15 C10 C7 124.1(7) . . ?
C15 C10 C11 116.4(8) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.0(7) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(8) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 Br1 121.7(7) . . ?
C12 C13 C14 118.0(9) . . ?
C14 C13 Br1 120.2(7) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(8) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.9(8) . . ?
C14 C15 H15 119.1 . . ?

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
Br1 C13 C14 C15 -178.5(6) . . . . ?
N1 C1 C2 C3 -175.1(8) . . . . ?
N1 C1 C2 C9 4.1(11) . . . . ?
N1 C1 C6 C5 174.7(7) . . . . ?
N1 C7 C8 C9 2.1(11) . . . . ?
N1 C7 C10 C11 6.4(10) . . . . ?
N1 C7 C10 C15 -169.8(7) . . . . ?
C1 N1 C7 C8 -0.1(10) . . . . ?
C1 N1 C7 C10 178.4(6) . . . . ?
C1 C2 C3 C4 1.0(13) . . . . ?
C1 C2 C9 C8 -2.0(11) . . . . ?
C2 C1 C6 C5 -2.0(12) . . . . ?
C2 C3 C4 C5 -2.7(14) . . . . ?
C3 C2 C9 C8 177.1(8) . . . . ?
C3 C4 C5 C6 2.0(13) . . . . ?
C4 C5 C6 C1 0.3(12) . . . . ?
C6 C1 C2 C3 1.4(12) . . . . ?
C6 C1 C2 C9 -179.5(7) . . . . ?
C7 N1 C1 C2 -3.0(11) . . . . ?
C7 N1 C1 C6 -179.5(7) . . . . ?
C7 C8 C9 C2 -0.8(12) . . . . ?
C7 C10 C11 C12 -178.1(7) . . . . ?
C7 C10 C15 C14 177.2(7) . . . . ?
C8 C7 C10 C11 -175.0(7) . . . . ?
C8 C7 C10 C15 8.7(11) . . . . ?
C9 C2 C3 C4 -178.0(8) . . . . ?
C10 C7 C8 C9 -176.4(7) . . . . ?
C10 C11 C12 C13 1.4(12) . . . . ?
C11 C10 C15 C14 0.9(11) . . . . ?
C11 C12 C13 Br1 177.8(6) . . . . ?
C11 C12 C13 C14 -0.6(12) . . . . ?
C12 C13 C14 C15 -0.1(12) . . . . ?
C13 C14 C15 C10 0.0(12) . . . . ?
C15 C10 C11 C12 -1.6(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
