# 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_KB1680_0m
_database_code_depnum_ccdc_archive 'CCDC 2391223'
loop_
_audit_author_name
_audit_author_address
'Dr. Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology 
India
;
_audit_update_record             
;
2024-10-15 deposited with the CCDC.	2025-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   6.1592(2)
_cell_length_b                   15.0585(7)
_cell_length_c                   17.1684(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1592.34(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4758
_cell_measurement_theta_min      2.3725
_cell_measurement_theta_max      22.3055

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6449
_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            17055
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         28.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3987
_reflns_number_gt                2404
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    1.000

_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)+(0.0681P)²] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 776 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3987
_refine_ls_number_parameters     203
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.989
_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
C1 C -0.2461(6) 0.2684(2) 0.30314(17) 0.0940(9) Uani 1 1 d . . . . .
H1A H -0.357997 0.231428 0.324629 0.141 Uiso 1 1 calc R U . . .
H1B H -0.151549 0.233140 0.271242 0.141 Uiso 1 1 calc R U . . .
H1C H -0.310870 0.314323 0.272040 0.141 Uiso 1 1 calc R U . . .
C2 C -0.1177(4) 0.30976(16) 0.36806(14) 0.0659(6) Uani 1 1 d . . . . .
C3 C -0.1990(4) 0.38246(17) 0.40926(15) 0.0677(6) Uani 1 1 d . . . . .
H3 H -0.334599 0.405175 0.396215 0.081 Uiso 1 1 calc R U . . .
C4 C -0.0837(4) 0.42106(15) 0.46838(14) 0.0603(6) Uani 1 1 d . . . . .
H4 H -0.142010 0.469372 0.494873 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1199(4) 0.38877(14) 0.48929(12) 0.0528(5) Uani 1 1 d . . . . .
C6 C 0.2005(4) 0.31535(14) 0.44976(13) 0.0594(6) Uani 1 1 d . . . . .
H6 H 0.334438 0.291647 0.463652 0.071 Uiso 1 1 calc R U . . .
C7 C 0.0826(4) 0.27729(16) 0.38985(13) 0.0648(6) Uani 1 1 d . . . . .
H7 H 0.139936 0.228599 0.363619 0.078 Uiso 1 1 calc R U . . .
C8 C 0.2518(4) 0.43163(14) 0.54976(12) 0.0545(6) Uani 1 1 d . . . . .
H8 H 0.375647 0.402551 0.567333 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3494(4) 0.54253(13) 0.63817(12) 0.0551(5) Uani 1 1 d . . . . .
H9 H 0.453672 0.497256 0.654945 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4690(3) 0.62019(17) 0.60091(14) 0.0590(6) Uani 1 1 d . . . . .
C11 C 0.7959(4) 0.66821(19) 0.5457(2) 0.0875(9) Uani 1 1 d . . . . .
H11A H 0.921167 0.642337 0.521422 0.131 Uiso 1 1 calc R U . . .
H11B H 0.841512 0.709742 0.584871 0.131 Uiso 1 1 calc R U . . .
H11C H 0.710519 0.698479 0.507206 0.131 Uiso 1 1 calc R U . . .
C12 C 0.2203(4) 0.57611(15) 0.70817(14) 0.0653(6) Uani 1 1 d . . . . .
H12A H 0.316921 0.609244 0.742032 0.078 Uiso 1 1 calc R U . . .
H12B H 0.108907 0.616628 0.689946 0.078 Uiso 1 1 calc R U . . .
C13 C 0.1145(4) 0.50344(15) 0.75461(12) 0.0577(5) Uani 1 1 d . . . . .
C14 C 0.2123(5) 0.47117(17) 0.82082(14) 0.0746(7) Uani 1 1 d . . . . .
H14 H 0.345001 0.494430 0.836727 0.089 Uiso 1 1 calc R U . . .
C15 C 0.1161(7) 0.4048(2) 0.86383(17) 0.0977(9) Uani 1 1 d . . . . .
H15 H 0.182756 0.384071 0.908889 0.117 Uiso 1 1 calc R U . . .
C16 C -0.0788(6) 0.3692(2) 0.8402(2) 0.0970(10) Uani 1 1 d . . . . .
H16 H -0.143246 0.323719 0.868646 0.116 Uiso 1 1 calc R U . . .
C17 C -0.1757(5) 0.4008(2) 0.77524(19) 0.0881(8) Uani 1 1 d . . . . .
H17 H -0.307629 0.376835 0.759312 0.106 Uiso 1 1 calc R U . . .
C18 C -0.0826(4) 0.46768(18) 0.73239(16) 0.0722(7) Uani 1 1 d . . . . .
H18 H -0.152576 0.489042 0.688193 0.087 Uiso 1 1 calc R U . . .
N1 N 0.2052(3) 0.50584(12) 0.57896(10) 0.0553(5) Uani 1 1 d . . . . .
O1 O 0.3811(18) 0.6855(13) 0.5791(16) 0.088(4) Uani 0.60(6) 1 d . U P A 1
O1D O 0.419(6) 0.6979(12) 0.609(2) 0.096(5) Uani 0.40(6) 1 d . U P A 2
O2 O 0.6669(2) 0.59901(10) 0.58145(10) 0.0736(5) Uani 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
C1 C2 1.502(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.379(4) . ?
C2 C3 1.396(3) . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 C8 1.468(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.258(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.459(3) . ?
C9 C10 1.523(3) . ?
C9 C12 1.527(3) . ?
C9 H9 0.9800 . ?
C10 O1 1.184(11) . ?
C10 O1D 1.218(18) . ?
C10 O2 1.304(3) . ?
C11 O2 1.447(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.503(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.375(3) . ?
C13 C18 1.382(3) . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.351(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(4) . ?
C17 H17 0.9300 . ?
C18 H18 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.5(2) . . ?
C7 C2 C1 121.7(2) . . ?
C3 C2 C1 120.8(2) . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 C8 119.9(2) . . ?
C4 C5 C8 121.8(2) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C2 C7 C6 121.6(2) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N1 C8 C5 123.1(2) . . ?
N1 C8 H8 118.4 . . ?
C5 C8 H8 118.4 . . ?
N1 C9 C10 107.01(17) . . ?
N1 C9 C12 110.92(18) . . ?
C10 C9 C12 109.15(17) . . ?
N1 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C12 C9 H9 109.9 . . ?
O1 C10 O2 123.4(6) . . ?
O1D C10 O2 120.1(13) . . ?
O1 C10 C9 123.4(6) . . ?
O1D C10 C9 124.4(10) . . ?
O2 C10 C9 111.8(2) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 113.70(18) . . ?
C13 C12 H12A 108.8 . . ?
C9 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C9 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 118.4(2) . . ?
C14 C13 C12 120.4(2) . . ?
C18 C13 C12 121.2(2) . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C8 N1 C9 118.37(18) . . ?
C10 O2 C11 116.48(19) . . ?

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
C7 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C8 176.9(2) . . . . ?
C4 C5 C6 C7 1.7(3) . . . . ?
C8 C5 C6 C7 -176.56(19) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C1 C2 C7 C6 -179.9(2) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C6 C5 C8 N1 168.3(2) . . . . ?
C4 C5 C8 N1 -9.9(3) . . . . ?
N1 C9 C10 O1 64.4(19) . . . . ?
C12 C9 C10 O1 -55.7(19) . . . . ?
N1 C9 C10 O1D 99(3) . . . . ?
C12 C9 C10 O1D -21(3) . . . . ?
N1 C9 C10 O2 -102.3(2) . . . . ?
C12 C9 C10 O2 137.6(2) . . . . ?
N1 C9 C12 C13 68.5(2) . . . . ?
C10 C9 C12 C13 -173.8(2) . . . . ?
C9 C12 C13 C14 97.4(2) . . . . ?
C9 C12 C13 C18 -82.9(3) . . . . ?
C18 C13 C14 C15 0.1(4) . . . . ?
C12 C13 C14 C15 179.8(2) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C13 0.7(4) . . . . ?
C14 C13 C18 C17 -0.8(4) . . . . ?
C12 C13 C18 C17 179.4(2) . . . . ?
C5 C8 N1 C9 -179.37(18) . . . . ?
C10 C9 N1 C8 108.4(2) . . . . ?
C12 C9 N1 C8 -132.66(19) . . . . ?
O1 C10 O2 C11 13.6(19) . . . . ?
O1D C10 O2 C11 -20(2) . . . . ?
C9 C10 O2 C11 -179.8(2) . . . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.026



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
