# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2519834'
loop_
_audit_author_name
_audit_author_address
'Aditya Rai' 'Banaras Hindu University'
_audit_update_record             
;
2026-01-02 deposited with the CCDC.	2026-05-08 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         ?
_chemical_formula_sum            'C15 H12 Cl N O'
_chemical_formula_weight         257.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.4472(2)
_cell_length_b                   9.62130(10)
_cell_length_c                   21.8930(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2621.87(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.463
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23950
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.038
_diffrn_reflns_theta_max         68.102
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2385
_reflns_number_gt                2102
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0766P)²+0.6995P] 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         2385
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_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
Cl1 Cl 0.14164(3) 0.52806(5) 0.49935(2) 0.06717(19) Uani 1 1 d . . . . .
O1 O 0.78414(9) 0.69679(11) 0.64878(6) 0.0622(3) Uani 1 1 d . . . . .
N1 N 0.82114(11) 0.46751(13) 0.66229(6) 0.0485(3) Uani 1 1 d . . . . .
C10 C 0.93101(13) 0.47378(15) 0.67752(7) 0.0482(4) Uani 1 1 d . . . . .
C9 C 0.75526(12) 0.57405(15) 0.64739(7) 0.0472(3) Uani 1 1 d . . . . .
C4 C 0.47466(12) 0.59153(15) 0.57578(7) 0.0486(3) Uani 1 1 d . . . . .
C8 C 0.64650(12) 0.53147(15) 0.62868(8) 0.0497(4) Uani 1 1 d . . . . .
H8 H 0.622183 0.442533 0.637936 0.060 Uiso 1 1 calc R U . . .
C1 C 0.27051(12) 0.55101(16) 0.52859(7) 0.0505(4) Uani 1 1 d . . . . .
C7 C 0.58292(12) 0.61845(15) 0.59880(7) 0.0506(4) Uani 1 1 d . . . . .
H7 H 0.610322 0.706890 0.591643 0.061 Uiso 1 1 calc R U . . .
C2 C 0.33126(15) 0.65949(18) 0.50766(8) 0.0595(4) Uani 1 1 d . . . . .
H2 H 0.304535 0.718895 0.477792 0.071 Uiso 1 1 calc R U . . .
C3 C 0.43244(14) 0.67954(17) 0.53140(9) 0.0598(4) Uani 1 1 d . . . . .
H3 H 0.473610 0.753694 0.517450 0.072 Uiso 1 1 calc R U . . .
C5 C 0.41111(14) 0.48108(18) 0.59552(8) 0.0598(4) Uani 1 1 d . . . . .
H5 H 0.437738 0.420244 0.624856 0.072 Uiso 1 1 calc R U . . .
C6 C 0.30922(14) 0.46046(18) 0.57223(9) 0.0611(4) Uani 1 1 d . . . . .
H6 H 0.267307 0.386610 0.585765 0.073 Uiso 1 1 calc R U . . .
C15 C 0.97414(15) 0.3646(2) 0.71038(8) 0.0648(5) Uani 1 1 d . . . . .
H15 H 0.930133 0.292097 0.723114 0.078 Uiso 1 1 calc R U . . .
C11 C 0.99765(13) 0.58123(19) 0.65867(9) 0.0626(4) Uani 1 1 d . . . . .
H11 H 0.970002 0.654933 0.636123 0.075 Uiso 1 1 calc R U . . .
C12 C 1.10555(16) 0.5777(2) 0.67372(11) 0.0756(5) Uani 1 1 d . . . . .
H12 H 1.149992 0.650238 0.661485 0.091 Uiso 1 1 calc R U . . .
C13 C 1.14802(16) 0.4699(3) 0.70616(10) 0.0807(7) Uani 1 1 d . . . . .
H13 H 1.220763 0.468907 0.715847 0.097 Uiso 1 1 calc R U . . .
C14 C 1.08253(18) 0.3627(3) 0.72443(10) 0.0821(6) Uani 1 1 d . . . . .
H14 H 1.111146 0.288606 0.746319 0.099 Uiso 1 1 calc R U . . .
H1 H 0.7937(15) 0.385(2) 0.6624(9) 0.062(5) Uiso 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
Cl1 C1 1.7411(16) . ?
O1 C9 1.2349(18) . ?
N1 C9 1.3526(19) . ?
N1 C10 1.409(2) . ?
N1 H1 0.86(2) . ?
C10 C15 1.382(2) . ?
C10 C11 1.388(2) . ?
C9 C8 1.472(2) . ?
C4 C3 1.392(2) . ?
C4 C5 1.393(2) . ?
C4 C7 1.462(2) . ?
C8 C7 1.325(2) . ?
C8 H8 0.9300 . ?
C1 C2 1.368(2) . ?
C1 C6 1.380(2) . ?
C7 H7 0.9300 . ?
C2 C3 1.376(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C15 C14 1.384(3) . ?
C15 H15 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 H14 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
C9 N1 C10 127.81(13) . . ?
C9 N1 H1 117.1(13) . . ?
C10 N1 H1 115.0(12) . . ?
C15 C10 C11 119.25(16) . . ?
C15 C10 N1 117.90(15) . . ?
C11 C10 N1 122.79(14) . . ?
O1 C9 N1 122.84(14) . . ?
O1 C9 C8 122.72(13) . . ?
N1 C9 C8 114.44(13) . . ?
C3 C4 C5 117.78(15) . . ?
C3 C4 C7 118.75(14) . . ?
C5 C4 C7 123.47(14) . . ?
C7 C8 C9 120.72(14) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C2 C1 C6 121.38(15) . . ?
C2 C1 Cl1 118.88(13) . . ?
C6 C1 Cl1 119.75(13) . . ?
C8 C7 C4 127.52(14) . . ?
C8 C7 H7 116.2 . . ?
C4 C7 H7 116.2 . . ?
C1 C2 C3 119.11(15) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.60(15) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C6 C5 C4 121.08(15) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.05(15) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C10 C15 C14 120.32(19) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C12 C11 C10 119.41(18) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.50(19) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?

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
C9 N1 C10 C15 158.67(16) . . . . ?
C9 N1 C10 C11 -24.2(2) . . . . ?
C10 N1 C9 O1 -4.3(3) . . . . ?
C10 N1 C9 C8 174.99(14) . . . . ?
O1 C9 C8 C7 16.3(2) . . . . ?
N1 C9 C8 C7 -163.08(15) . . . . ?
C9 C8 C7 C4 178.33(14) . . . . ?
C3 C4 C7 C8 -162.11(17) . . . . ?
C5 C4 C7 C8 17.3(3) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
Cl1 C1 C2 C3 178.87(14) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C7 C4 C3 C2 179.71(16) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C7 C4 C5 C6 179.97(16) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
Cl1 C1 C6 C5 -179.21(14) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
N1 C10 C15 C14 177.38(17) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
N1 C10 C11 C12 -177.82(17) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C10 C15 C14 C13 0.4(3) . . . . ?

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
C8 H8 O1 0.93 2.65 3.3627(18) 134.3 8_755 yes
C11 H11 O1 0.93 2.36 2.889(2) 115.4 . yes
N1 H1 O1 0.86(2) 2.08(2) 2.9307(17) 170.4(18) 8_755 yes

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.038

