# 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_AS_R_205_2765_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2544867'
loop_
_audit_author_name
_audit_author_address
'RAMAN KUMAR'
;INDIAN INSTITUTE OF TECHNOLOGY ROORKEE
India
;
_audit_update_record             
;
2026-04-09 deposited with the CCDC.	2026-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N2 O'
_chemical_formula_sum            'C16 H22 N2 O'
_chemical_formula_weight         258.35

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.913(2)
_cell_length_b                   11.952(4)
_cell_length_c                   19.728(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.761(10)
_cell_angle_gamma                90
_cell_volume                     1389.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4953
_cell_measurement_theta_min      2.6829
_cell_measurement_theta_max      22.9723

_exptl_crystal_description       plate
_exptl_crystal_colour            'lustrous light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 QUEST photon III C7'
_diffrn_measurement_method       '\ f and \ w scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            21788
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.683
_diffrn_reflns_theta_max         25.132
_diffrn_reflns_theta_full        25.132
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2456
_reflns_number_gt                1994
_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       
"Bruker APEX4 v2022.1-0'(Bruker AXS Inc., 2022)"
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  "APEX4 v2022.1-0'(Bruker AXS Inc., 2022)"
_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)+(0.0331P)²+1.2567P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2456
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
O1 O 1.2967(3) 0.75682(13) 0.69039(8) 0.0310(4) Uani 1 1 d . . . . .
N1 N 0.8240(3) 0.59156(15) 0.63738(10) 0.0252(4) Uani 1 1 d . . . . .
N2 N 0.9718(3) 0.66062(15) 0.67647(9) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.5096(3) 0.46947(18) 0.64837(11) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.3309(3) 0.43709(18) 0.68589(12) 0.0253(5) Uani 1 1 d . . . . .
H2 H 0.325681 0.462973 0.731259 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1602(4) 0.36726(19) 0.65754(12) 0.0270(5) Uani 1 1 d . . . . .
H3 H 0.040897 0.344338 0.683845 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1641(4) 0.33144(19) 0.59142(12) 0.0284(6) Uani 1 1 d . . . . .
H4 H 0.045690 0.285153 0.571715 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3418(4) 0.36298(19) 0.55328(12) 0.0283(5) Uani 1 1 d . . . . .
H5 H 0.344576 0.338062 0.507624 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5138(4) 0.43051(18) 0.58191(12) 0.0254(5) Uani 1 1 d . . . . .
H6 H 0.636126 0.450574 0.556035 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6870(3) 0.54678(18) 0.67699(11) 0.0228(5) Uani 1 1 d . . . . .
C8 C 0.9229(4) 0.66459(19) 0.74789(11) 0.0266(5) Uani 1 1 d . . . . .
H8A H 0.877783 0.740844 0.761001 0.032 Uiso 1 1 calc R U . . .
H8B H 1.055990 0.640604 0.778156 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7240(3) 0.58136(18) 0.75082(12) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.587091 0.622624 0.763886 0.028 Uiso 1 1 calc R U . . .
C10 C 1.1613(4) 0.70387(18) 0.65203(12) 0.0248(5) Uani 1 1 d . . . . .
C11 C 0.7757(3) 0.48479(18) 0.80092(11) 0.0233(5) Uani 1 1 d . . . . .
H11A H 0.937831 0.464658 0.799982 0.028 Uiso 1 1 calc R U . . .
H11B H 0.685331 0.419040 0.784432 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7285(3) 0.50663(18) 0.87514(11) 0.0239(5) Uani 1 1 d . . . . .
C13 C 0.8426(4) 0.61412(19) 0.90272(12) 0.0272(5) Uani 1 1 d . . . . .
H13A H 1.006457 0.609328 0.898916 0.041 Uiso 1 1 calc R U . . .
H13B H 0.813633 0.623669 0.950576 0.041 Uiso 1 1 calc R U . . .
H13C H 0.780632 0.678229 0.876334 0.041 Uiso 1 1 calc R U . . .
C14 C 1.1891(4) 0.6875(2) 0.57795(12) 0.0286(6) Uani 1 1 d . . . . .
H14A H 1.096148 0.742464 0.551351 0.043 Uiso 1 1 calc R U . . .
H14B H 1.140380 0.611830 0.564389 0.043 Uiso 1 1 calc R U . . .
H14C H 1.348883 0.697623 0.569603 0.043 Uiso 1 1 calc R U . . .
C15 C 0.4716(4) 0.5154(2) 0.88115(12) 0.0286(5) Uani 1 1 d . . . . .
H15A H 0.410595 0.579308 0.854376 0.043 Uiso 1 1 calc R U . . .
H15B H 0.443022 0.525997 0.928963 0.043 Uiso 1 1 calc R U . . .
H15C H 0.397270 0.446575 0.863961 0.043 Uiso 1 1 calc R U . . .
C16 C 0.8223(4) 0.4082(2) 0.91791(12) 0.0286(5) Uani 1 1 d . . . . .
H16A H 0.754794 0.338445 0.899555 0.043 Uiso 1 1 calc R U . . .
H16B H 0.784855 0.417804 0.965020 0.043 Uiso 1 1 calc R U . . .
H16C H 0.987472 0.404940 0.916614 0.043 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
O1 C10 1.230(3) . ?
N1 C7 1.288(3) . ?
N1 N2 1.389(2) . ?
N2 C10 1.358(3) . ?
N2 C8 1.463(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.394(3) . ?
C1 C7 1.474(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.512(3) . ?
C8 C9 1.545(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.534(3) . ?
C9 H9 1.0000 . ?
C10 C14 1.497(3) . ?
C11 C12 1.536(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.525(3) . ?
C12 C13 1.530(3) . ?
C12 C15 1.537(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 N2 107.99(18) . . ?
C10 N2 N1 121.93(18) . . ?
C10 N2 C8 124.38(18) . . ?
N1 N2 C8 112.86(17) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 C7 120.1(2) . . ?
C2 C1 C7 121.1(2) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C1 119.4(2) . . ?
N1 C7 C9 114.99(19) . . ?
C1 C7 C9 125.57(19) . . ?
N2 C8 C9 103.13(17) . . ?
N2 C8 H8A 111.1 . . ?
C9 C8 H8A 111.1 . . ?
N2 C8 H8B 111.1 . . ?
C9 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C7 C9 C11 114.84(18) . . ?
C7 C9 C8 100.95(17) . . ?
C11 C9 C8 113.39(18) . . ?
C7 C9 H9 109.1 . . ?
C11 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
O1 C10 N2 119.4(2) . . ?
O1 C10 C14 123.3(2) . . ?
N2 C10 C14 117.22(19) . . ?
C9 C11 C12 116.37(18) . . ?
C9 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C9 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C16 C12 C13 108.77(18) . . ?
C16 C12 C11 108.03(18) . . ?
C13 C12 C11 111.85(18) . . ?
C16 C12 C15 109.05(18) . . ?
C13 C12 C15 108.94(18) . . ?
C11 C12 C15 110.15(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 N1 N2 C10 167.91(19) . . . . ?
C7 N1 N2 C8 -2.1(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C1 C2 C3 177.7(2) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C7 C1 C6 C5 -176.4(2) . . . . ?
N2 N1 C7 C1 179.63(18) . . . . ?
N2 N1 C7 C9 0.4(2) . . . . ?
C6 C1 C7 N1 10.8(3) . . . . ?
C2 C1 C7 N1 -166.9(2) . . . . ?
C6 C1 C7 C9 -170.1(2) . . . . ?
C2 C1 C7 C9 12.3(3) . . . . ?
C10 N2 C8 C9 -166.92(19) . . . . ?
N1 N2 C8 C9 2.8(2) . . . . ?
N1 C7 C9 C11 -121.1(2) . . . . ?
C1 C7 C9 C11 59.7(3) . . . . ?
N1 C7 C9 C8 1.3(2) . . . . ?
C1 C7 C9 C8 -177.90(19) . . . . ?
N2 C8 C9 C7 -2.3(2) . . . . ?
N2 C8 C9 C11 121.08(19) . . . . ?
N1 N2 C10 O1 -173.93(19) . . . . ?
C8 N2 C10 O1 -5.1(3) . . . . ?
N1 N2 C10 C14 8.3(3) . . . . ?
C8 N2 C10 C14 177.17(19) . . . . ?
C7 C9 C11 C12 -158.19(17) . . . . ?
C8 C9 C11 C12 86.5(2) . . . . ?
C9 C11 C12 C16 -171.88(17) . . . . ?
C9 C11 C12 C13 -52.2(2) . . . . ?
C9 C11 C12 C15 69.1(2) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.049

