# Supplementary Information (SI) for RSC Mechanochemistry.
# 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_KB1676_0m
_database_code_depnum_ccdc_archive 'CCDC 2391222'
loop_
_audit_author_name
_audit_author_address
'Dr. Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology 
India
;
#Added by publCIF



_audit_update_record             
;
2024-10-15 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_publcif_datablock.id            {a56d5de1-383d-4518-a151-51f61bb819c9}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 Br N O'
_chemical_formula_sum            'C13 H16 Br N O'
_chemical_formula_weight         282.18

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'
Br Br -0.2901 2.4595 '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                   5.2539(2)
_cell_length_b                   20.4717(8)
_cell_length_c                   11.9662(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.284(2)
_cell_angle_gamma                90
_cell_volume                     1266.36(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4744
_cell_measurement_theta_min      2.6365
_cell_measurement_theta_max      27.222

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.225
_shelx_estimated_absorpt_T_min   0.537
_shelx_estimated_absorpt_T_max   0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5919
_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
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9577
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3120
_reflns_number_gt                2370
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0290P)²+0.1827P] 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_number_reflns         3120
_refine_ls_number_parameters     161
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.5203(3) 0.70657(8) 0.31645(13) 0.0387(4) Uani 1 1 d . . . . .
C2 C 0.4988(4) 0.71852(10) 0.20160(15) 0.0513(5) Uani 1 1 d . . . . .
H2 H 0.612303 0.747175 0.175373 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3076(4) 0.68762(10) 0.12608(15) 0.0555(5) Uani 1 1 d . . . . .
H3 H 0.293628 0.694994 0.048530 0.067 Uiso 1 1 calc R U . . .
C4 C 0.1376(4) 0.64596(10) 0.16492(15) 0.0535(5) Uani 1 1 d . . . . .
H4 H 0.005429 0.626270 0.114006 0.064 Uiso 1 1 calc R U . . .
C5 C 0.1637(3) 0.63346(9) 0.27972(14) 0.0448(4) Uani 1 1 d . . . . .
H5 H 0.048431 0.605040 0.305267 0.054 Uiso 1 1 calc R U . . .
C6 C 0.3599(3) 0.66257(7) 0.35867(13) 0.0361(3) Uani 1 1 d . . . . .
C7 C 0.3947(3) 0.64436(8) 0.47947(13) 0.0380(4) Uani 1 1 d . . . . .
H7 H 0.536262 0.661120 0.529039 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3033(3) 0.59039(9) 0.63894(13) 0.0411(4) Uani 1 1 d . . . . .
H8 H 0.464993 0.611971 0.673136 0.049 Uiso 1 1 calc R U . . .
C9 C 0.0877(4) 0.61317(9) 0.69935(16) 0.0543(5) Uani 1 1 d . . . . .
H9A H 0.073560 0.660362 0.694396 0.065 Uiso 1 1 calc R U . . .
H9B H -0.075309 0.594658 0.661935 0.065 Uiso 1 1 calc R U . . .
C10 C 0.1392(4) 0.59275(9) 0.82350(15) 0.0517(5) Uani 1 1 d . . . . .
H10A H 0.293875 0.614468 0.862526 0.062 Uiso 1 1 calc R U . . .
H10B H -0.004524 0.606317 0.858922 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1737(3) 0.51988(8) 0.83544(12) 0.0379(4) Uani 1 1 d . . . . .
H11 H 0.011543 0.499161 0.799375 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3853(3) 0.49614(9) 0.77510(14) 0.0465(4) Uani 1 1 d . . . . .
H12A H 0.394709 0.448865 0.779468 0.056 Uiso 1 1 calc R U . . .
H12B H 0.550029 0.513509 0.813011 0.056 Uiso 1 1 calc R U . . .
C13 C 0.3380(4) 0.51701(9) 0.65078(14) 0.0467(4) Uani 1 1 d . . . . .
H13A H 0.483413 0.503596 0.616365 0.056 Uiso 1 1 calc R U . . .
H13B H 0.184400 0.495324 0.610625 0.056 Uiso 1 1 calc R U . . .
N1 N 0.2421(3) 0.60728(7) 0.51845(11) 0.0490(4) Uani 1 1 d . . . . .
O1 O 0.2270(3) 0.49957(8) 0.95160(11) 0.0579(4) Uani 1 1 d . . . . .
H1O H 0.363(8) 0.507(3) 0.978(4) 0.087 Uiso 0.5 1 d . U P . .
H2O H 0.122(9) 0.501(3) 0.980(4) 0.087 Uiso 0.5 1 d . U P . .
Br1 Br 0.7829(5) 0.7521(2) 0.4192(3) 0.0526(5) Uani 0.65(3) 1 d . U P A 1
Br1D Br 0.7652(15) 0.7577(4) 0.4110(7) 0.0670(13) Uani 0.35(3) 1 d . U P A 2


_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
C1 C2 1.381(2) . ?
C1 C6 1.389(2) . ?
C1 Br1D 1.874(6) . ?
C1 Br1 1.918(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.472(2) . ?
C7 N1 1.253(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.462(2) . ?
C8 C13 1.517(2) . ?
C8 C9 1.522(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.520(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.506(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O1 1.4299(19) . ?
C11 C12 1.510(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.525(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O1 H1O 0.75(4) . ?
O1 H2O 0.70(4) . ?

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 C1 C6 121.99(16) . . ?
C2 C1 Br1D 115.3(3) . . ?
C6 C1 Br1D 122.6(3) . . ?
C2 C1 Br1 118.27(17) . . ?
C6 C1 Br1 119.74(16) . . ?
C3 C2 C1 119.45(17) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.28(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.78(17) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.53(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 116.86(14) . . ?
C1 C6 C7 122.96(15) . . ?
C5 C6 C7 120.13(14) . . ?
N1 C7 C6 122.90(15) . . ?
N1 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
N1 C8 C13 109.16(14) . . ?
N1 C8 C9 110.18(14) . . ?
C13 C8 C9 110.27(14) . . ?
N1 C8 H8 109.1 . . ?
C13 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C10 C9 C8 111.25(15) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 111.24(15) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O1 C11 C10 112.31(14) . . ?
O1 C11 C12 109.75(13) . . ?
C10 C11 C12 111.08(14) . . ?
O1 C11 H11 107.8 . . ?
C10 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C11 C12 C13 111.75(13) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C8 C13 C12 111.38(14) . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C7 N1 C8 117.91(14) . . ?
C11 O1 H1O 111(4) . . ?
C11 O1 H2O 116(4) . . ?
H1O O1 H2O 125(6) . . ?

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 2.1(3) . . . . ?
Br1D C1 C2 C3 -174.1(4) . . . . ?
Br1 C1 C2 C3 -178.43(19) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -2.1(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C2 C1 C6 C5 -3.7(2) . . . . ?
Br1D C1 C6 C5 172.2(4) . . . . ?
Br1 C1 C6 C5 176.83(18) . . . . ?
C2 C1 C6 C7 174.04(16) . . . . ?
Br1D C1 C6 C7 -10.1(4) . . . . ?
Br1 C1 C6 C7 -5.4(2) . . . . ?
C4 C5 C6 C1 2.5(2) . . . . ?
C4 C5 C6 C7 -175.32(16) . . . . ?
C1 C6 C7 N1 176.21(16) . . . . ?
C5 C6 C7 N1 -6.1(2) . . . . ?
N1 C8 C9 C10 176.74(15) . . . . ?
C13 C8 C9 C10 56.2(2) . . . . ?
C8 C9 C10 C11 -56.7(2) . . . . ?
C9 C10 C11 O1 178.93(14) . . . . ?
C9 C10 C11 C12 55.6(2) . . . . ?
O1 C11 C12 C13 -179.62(15) . . . . ?
C10 C11 C12 C13 -54.8(2) . . . . ?
N1 C8 C13 C12 -176.38(14) . . . . ?
C9 C8 C13 C12 -55.20(19) . . . . ?
C11 C12 C13 C8 55.0(2) . . . . ?
C6 C7 N1 C8 177.30(14) . . . . ?
C13 C8 N1 C7 -119.17(17) . . . . ?
C9 C8 N1 C7 119.60(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O O1 0.75(4) 2.17(4) 2.895(3) 164(6) 3_667 yes
O1 H2O O1 0.70(4) 2.14(4) 2.832(3) 173(6) 3_567 yes

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.045


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
