# Supplementary Information (SI) for CrystEngComm.
# 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 1538432'
loop_
_audit_author_name
_audit_author_address
'Dr.Shibu M Eappen'
;STIC, CUSAT
India
;
_audit_update_record             
;
2026-03-11 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N O'
_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_weight         303.39

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   10.2885(9)
_cell_length_b                   16.1075(17)
_cell_length_c                   9.9824(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1654.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2097
_cell_measurement_theta_min      4.800
_cell_measurement_theta_max      43.170

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10128
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_full        24.984
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.863
_reflns_number_total             2514
_reflns_number_gt                1797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_max     0.710
_reflns_Friedel_fraction_full    0.710

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0607P)²+0.1716P] 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_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2514
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.970
_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 0.5907(3) 0.7215(2) 0.2682(5) 0.0580(10) Uani 1 1 d . . . . .
H1 H 0.5346 0.7066 0.3371 0.070 Uiso 1 1 calc R U . . .
C2 C 0.6084(4) 0.6683(3) 0.1609(6) 0.0721(13) Uani 1 1 d . . . . .
H2 H 0.5638 0.6182 0.1583 0.087 Uiso 1 1 calc R U . . .
C3 C 0.6911(4) 0.6889(3) 0.0583(5) 0.0701(13) Uani 1 1 d . . . . .
H3 H 0.7025 0.6531 -0.0139 0.084 Uiso 1 1 calc R U . . .
C4 C 0.7561(4) 0.7625(3) 0.0639(5) 0.0679(12) Uani 1 1 d . . . . .
H4 H 0.8125 0.7768 -0.0052 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7398(4) 0.8159(2) 0.1700(4) 0.0538(10) Uani 1 1 d . . . . .
H5 H 0.7857 0.8656 0.1721 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6556(3) 0.7966(2) 0.2742(4) 0.0430(8) Uani 1 1 d . . . . .
C7 C 0.6354(3) 0.8545(2) 0.3914(4) 0.0444(9) Uani 1 1 d . . . . .
H20 H 0.5924 0.8231 0.4629 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7922(4) 0.7628(3) 0.5935(4) 0.0546(10) Uani 1 1 d . . . . .
H8 H 0.7178 0.7387 0.5576 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8585(4) 0.7215(3) 0.6911(5) 0.0667(12) Uani 1 1 d . . . . .
H9 H 0.8290 0.6700 0.7203 0.080 Uiso 1 1 calc R U . . .
C10 C 0.9708(4) 0.7562(3) 0.7476(5) 0.0676(12) Uani 1 1 d . . . . .
H10 H 1.0146 0.7286 0.8159 0.081 Uiso 1 1 calc R U . . .
C11 C 1.0148(4) 0.8298(3) 0.7022(5) 0.0629(12) Uani 1 1 d . . . . .
H11 H 1.0896 0.8524 0.7398 0.075 Uiso 1 1 calc R U . . .
C12 C 0.9514(3) 0.8732(3) 0.6003(4) 0.0518(10) Uani 1 1 d . . . . .
C13 C 0.8326(3) 0.8409(2) 0.5453(4) 0.0444(9) Uani 1 1 d . . . . .
C14 C 0.7652(3) 0.8866(2) 0.4461(4) 0.0441(9) Uani 1 1 d . . . . .
C15 C 0.8184(3) 0.9591(2) 0.3988(4) 0.0521(10) Uani 1 1 d . . . . .
C16 C 0.9400(4) 0.9890(3) 0.4480(5) 0.0603(11) Uani 1 1 d . . . . .
H16 H 0.9765 1.0369 0.4121 0.072 Uiso 1 1 calc R U . . .
C17 C 1.0016(4) 0.9477(3) 0.5464(5) 0.0609(12) Uani 1 1 d . . . . .
H17 H 1.0792 0.9687 0.5799 0.073 Uiso 1 1 calc R U . . .
C18 C 0.5089(4) 0.9733(3) 0.4745(5) 0.0720(13) Uani 1 1 d . . . . .
H18A H 0.5778 1.0099 0.5048 0.086 Uiso 1 1 calc R U . . .
H18B H 0.4844 0.9367 0.5474 0.086 Uiso 1 1 calc R U . . .
C19 C 0.3931(5) 1.0225(4) 0.4248(8) 0.120(2) Uani 1 1 d . . . . .
H19A H 0.3297 1.0295 0.4958 0.144 Uiso 1 1 calc R U . . .
H19B H 0.4202 1.0769 0.3939 0.144 Uiso 1 1 calc R U . . .
C20 C 0.3371(4) 0.9739(3) 0.3131(6) 0.0876(16) Uani 1 1 d . . . . .
H20A H 0.3317 1.0078 0.2329 0.105 Uiso 1 1 calc R U . . .
H20B H 0.2503 0.9550 0.3360 0.105 Uiso 1 1 calc R U . . .
C21 C 0.4264(3) 0.9003(3) 0.2901(5) 0.0617(11) Uani 1 1 d . . . . .
H21A H 0.3914 0.8505 0.3311 0.074 Uiso 1 1 calc R U . . .
H21B H 0.4389 0.8904 0.1951 0.074 Uiso 1 1 calc R U . . .
N1 N 0.5500(3) 0.92518(18) 0.3548(3) 0.0495(8) Uani 1 1 d . . . . .
O1 O 0.7610(2) 1.00735(15) 0.3024(3) 0.0650(8) Uani 1 1 d . . . . .
H1A H 0.7099 0.9791 0.2589 0.098 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
C1 C6 1.383(5) . ?
C1 C2 1.383(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.511(5) . ?
C7 N1 1.483(4) . ?
C7 C14 1.533(5) . ?
C7 H20 0.9800 . ?
C8 C9 1.363(6) . ?
C8 C13 1.410(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.402(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.349(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(6) . ?
C11 H11 0.9300 . ?
C12 C17 1.413(6) . ?
C12 C13 1.436(5) . ?
C13 C14 1.415(5) . ?
C14 C15 1.374(5) . ?
C15 O1 1.371(5) . ?
C15 C16 1.427(5) . ?
C16 C17 1.346(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.486(5) . ?
C18 C19 1.514(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.478(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.518(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N1 1.482(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
O1 H1A 0.8200 . ?

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
C6 C1 C2 120.8(4) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.7(4) . . ?
C1 C6 C7 120.4(3) . . ?
C5 C6 C7 121.9(3) . . ?
N1 C7 C6 111.4(3) . . ?
N1 C7 C14 110.2(3) . . ?
C6 C7 C14 111.3(3) . . ?
N1 C7 H20 107.9 . . ?
C6 C7 H20 107.9 . . ?
C14 C7 H20 107.9 . . ?
C9 C8 C13 122.1(4) . . ?
C9 C8 H8 118.9 . . ?
C13 C8 H8 118.9 . . ?
C8 C9 C10 120.4(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.9(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C17 122.1(4) . . ?
C11 C12 C13 119.7(4) . . ?
C17 C12 C13 118.2(4) . . ?
C8 C13 C14 123.9(3) . . ?
C8 C13 C12 116.3(4) . . ?
C14 C13 C12 119.8(3) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 C7 120.8(3) . . ?
C13 C14 C7 120.1(3) . . ?
O1 C15 C14 123.5(3) . . ?
O1 C15 C16 115.4(3) . . ?
C14 C15 C16 121.2(4) . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 121.8(4) . . ?
C16 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
N1 C18 C19 103.5(4) . . ?
N1 C18 H18A 111.1 . . ?
C19 C18 H18A 111.1 . . ?
N1 C18 H18B 111.1 . . ?
C19 C18 H18B 111.1 . . ?
H18A C18 H18B 109.0 . . ?
C20 C19 C18 106.1(4) . . ?
C20 C19 H19A 110.5 . . ?
C18 C19 H19A 110.5 . . ?
C20 C19 H19B 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
C19 C20 C21 106.9(4) . . ?
C19 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
C19 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
N1 C21 C20 104.1(3) . . ?
N1 C21 H21A 110.9 . . ?
C20 C21 H21A 110.9 . . ?
N1 C21 H21B 110.9 . . ?
C20 C21 H21B 110.9 . . ?
H21A C21 H21B 109.0 . . ?
C21 N1 C7 114.1(3) . . ?
C21 N1 C18 104.3(3) . . ?
C7 N1 C18 111.8(3) . . ?
C15 O1 H1A 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
C6 C1 C2 C3 0.2(7) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
C2 C1 C6 C7 179.8(3) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C1 C6 C7 N1 -103.7(4) . . . . ?
C5 C6 C7 N1 76.9(4) . . . . ?
C1 C6 C7 C14 132.9(3) . . . . ?
C5 C6 C7 C14 -46.5(5) . . . . ?
C13 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 -1.8(6) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C17 -175.9(4) . . . . ?
C10 C11 C12 C13 2.8(6) . . . . ?
C9 C8 C13 C14 -178.7(4) . . . . ?
C9 C8 C13 C12 2.8(5) . . . . ?
C11 C12 C13 C8 -4.2(5) . . . . ?
C17 C12 C13 C8 174.5(3) . . . . ?
C11 C12 C13 C14 177.2(3) . . . . ?
C17 C12 C13 C14 -4.1(5) . . . . ?
C8 C13 C14 C15 -175.0(3) . . . . ?
C12 C13 C14 C15 3.5(5) . . . . ?
C8 C13 C14 C7 4.2(5) . . . . ?
C12 C13 C14 C7 -177.3(3) . . . . ?
N1 C7 C14 C15 -32.9(4) . . . . ?
C6 C7 C14 C15 91.2(4) . . . . ?
N1 C7 C14 C13 148.0(3) . . . . ?
C6 C7 C14 C13 -88.0(4) . . . . ?
C13 C14 C15 O1 179.6(3) . . . . ?
C7 C14 C15 O1 0.4(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C7 C14 C15 C16 -179.3(3) . . . . ?
O1 C15 C16 C17 177.5(4) . . . . ?
C14 C15 C16 C17 -2.8(6) . . . . ?
C15 C16 C17 C12 2.2(6) . . . . ?
C11 C12 C17 C16 179.9(4) . . . . ?
C13 C12 C17 C16 1.2(6) . . . . ?
N1 C18 C19 C20 26.5(6) . . . . ?
C18 C19 C20 C21 -4.6(6) . . . . ?
C19 C20 C21 N1 -19.1(6) . . . . ?
C20 C21 N1 C7 158.1(4) . . . . ?
C20 C21 N1 C18 35.8(4) . . . . ?
C6 C7 N1 C21 51.0(4) . . . . ?
C14 C7 N1 C21 175.0(3) . . . . ?
C6 C7 N1 C18 169.1(3) . . . . ?
C14 C7 N1 C18 -66.9(4) . . . . ?
C19 C18 N1 C21 -38.7(4) . . . . ?
C19 C18 N1 C7 -162.5(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
O1 H1A N1 0.82 2.09 2.596(4) 119.5 .

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035

