# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_anfinal
_database_code_depnum_ccdc_archive 'CCDC 2420729'
loop_
_audit_author_name
_audit_author_address
'Asadujjaman Nur'
;Jadavpur University
India
;
_audit_update_record             
;
2025-01-31 deposited with the CCDC.	2025-11-04 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O2'
_chemical_formula_sum            'C20 H16 O2'
_chemical_formula_weight         288.33
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1390(2)
_cell_length_b                   12.3696(5)
_cell_length_c                   12.8834(5)
_cell_angle_alpha                106.2860(10)
_cell_angle_beta                 96.7910(10)
_cell_angle_gamma                101.9120(10)
_cell_volume                     755.53(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      33.57
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.9340.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33271
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.577
_diffrn_reflns_theta_min         3.414
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4218
_reflns_number_total             5472
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         5472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0978
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+0.4823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1837
_refine_ls_wR_factor_ref         0.1955
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C10(H10), C12(H12), C11(H11), C1(H1), C2(H2), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.1443(3) 0.50225(10) 0.18351(10) 0.0384(3) Uani 1 1 d . . . . .
O002 O -0.1169(4) 0.13476(14) 0.06448(17) 0.0689(5) Uani 1 1 d . . . . .
C1 C 0.2364(5) 0.6379(2) 0.49203(18) 0.0555(6) Uani 1 1 d . . . . .
H1 H 0.249227 0.565961 0.498278 0.067 Uiso 1 1 calc R U . . .
C2 C 0.0995(5) 0.7051(3) 0.55964(19) 0.0671(7) Uani 1 1 d . . . . .
H2 H 0.021359 0.678408 0.612250 0.081 Uiso 1 1 calc R U . . .
C3 C 0.0781(5) 0.8116(3) 0.5494(2) 0.0700(8) Uani 1 1 d . . . . .
H3 H -0.014588 0.855537 0.595343 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1923(5) 0.8537(2) 0.4722(2) 0.0589(6) Uani 1 1 d . . . . .
H4 H 0.176207 0.925076 0.465514 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3534(4) 0.67983(17) 0.41528(15) 0.0408(4) Uani 1 1 d . . . . .
C6 C 0.3319(4) 0.78726(17) 0.40457(16) 0.0423(4) Uani 1 1 d . . . . .
C7 C 0.4758(4) 0.80905(15) 0.31813(16) 0.0397(4) Uani 1 1 d . . . . .
C8 C 0.5880(4) 0.71565(15) 0.27626(15) 0.0365(4) Uani 1 1 d . . . . .
C9 C 0.7461(4) 0.71652(18) 0.19695(17) 0.0459(5) Uani 1 1 d . . . . .
H9 H 0.822390 0.654741 0.170071 0.055 Uiso 1 1 calc R U . . .
C10 C 0.7891(5) 0.8114(2) 0.15807(19) 0.0534(5) Uani 1 1 d . . . . .
H10 H 0.897566 0.813702 0.105442 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6726(5) 0.9024(2) 0.1966(2) 0.0570(6) Uani 1 1 d . . . . .
H11 H 0.699470 0.964306 0.168183 0.068 Uiso 1 1 calc R U . . .
C12 C 0.5164(5) 0.90273(18) 0.2771(2) 0.0516(5) Uani 1 1 d . . . . .
H12 H 0.439736 0.964546 0.303265 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5152(4) 0.62433(15) 0.33355(15) 0.0382(4) Uani 1 1 d . . . . .
H13 H 0.681869 0.618043 0.374389 0.046 Uiso 1 1 calc R U . . .
C14 C 0.3644(4) 0.50639(15) 0.25900(14) 0.0363(4) Uani 1 1 d . . . . .
C15 C 0.3823(4) 0.39783(16) 0.25078(15) 0.0393(4) Uani 1 1 d . . . . .
H15 H 0.513175 0.376975 0.291991 0.047 Uiso 1 1 calc R U . . .
C16 C 0.1616(4) 0.31952(15) 0.16639(15) 0.0357(4) Uani 1 1 d . . . . .
C17 C 0.0241(4) 0.38754(15) 0.12776(14) 0.0355(4) Uani 1 1 d . . . . .
C18 C -0.2115(4) 0.36442(19) 0.03911(17) 0.0480(5) Uani 1 1 d . . . . .
H18A H -0.342291 0.403658 0.068406 0.072 Uiso 1 1 calc R U . . .
H18B H -0.292263 0.282222 0.010245 0.072 Uiso 1 1 calc R U . . .
H18C H -0.152513 0.392422 -0.018715 0.072 Uiso 1 1 calc R U . . .
C19 C 0.0934(4) 0.19100(16) 0.12720(18) 0.0444(4) Uani 1 1 d . . . . .
C20 C 0.2928(6) 0.1324(2) 0.1675(3) 0.0671(7) Uani 1 1 d . . . . .
H20A H 0.220757 0.049589 0.139406 0.101 Uiso 1 1 calc R U . . .
H20B H 0.326690 0.156848 0.246492 0.101 Uiso 1 1 calc R U . . .
H20C H 0.459069 0.153225 0.142408 0.101 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
O001 C14 1.384(2) . ?
O001 C17 1.368(2) . ?
O002 C19 1.213(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C3 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C1 1.381(3) . ?
C5 C6 1.399(3) . ?
C6 C4 1.393(3) . ?
C7 C6 1.463(3) . ?
C7 C12 1.392(3) . ?
C8 C7 1.399(3) . ?
C8 C9 1.380(3) . ?
C8 C13 1.523(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C11 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C5 1.520(3) . ?
C13 H13 0.9800 . ?
C14 C13 1.491(2) . ?
C14 C15 1.340(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.439(3) . ?
C16 C17 1.361(2) . ?
C16 C19 1.478(2) . ?
C17 C18 1.483(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.496(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C17 O001 C14 107.43(13) . . ?
C2 C1 H1 120.7 . . ?
C5 C1 H1 120.7 . . ?
C5 C1 C2 118.7(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C6 118.8(2) . . ?
C6 C4 H4 120.6 . . ?
C1 C5 C6 120.9(2) . . ?
C1 C5 C13 128.8(2) . . ?
C6 C5 C13 110.27(17) . . ?
C4 C6 C5 120.0(2) . . ?
C4 C6 C7 131.3(2) . . ?
C5 C6 C7 108.72(17) . . ?
C8 C7 C6 108.90(17) . . ?
C12 C7 C6 131.27(19) . . ?
C12 C7 C8 119.8(2) . . ?
C7 C8 C13 110.05(17) . . ?
C9 C8 C7 120.92(18) . . ?
C9 C8 C13 129.00(17) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.7(2) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.5 . . ?
C11 C12 C7 118.9(2) . . ?
C11 C12 H12 120.5 . . ?
C5 C13 C8 102.04(15) . . ?
C5 C13 H13 108.8 . . ?
C8 C13 H13 108.8 . . ?
C14 C13 C5 113.16(16) . . ?
C14 C13 C8 114.97(15) . . ?
C14 C13 H13 108.8 . . ?
O001 C14 C13 116.08(15) . . ?
C15 C14 O001 109.40(15) . . ?
C15 C14 C13 134.40(17) . . ?
C14 C15 H15 126.3 . . ?
C14 C15 C16 107.35(16) . . ?
C16 C15 H15 126.3 . . ?
C15 C16 C19 128.02(17) . . ?
C17 C16 C15 106.21(15) . . ?
C17 C16 C19 125.76(18) . . ?
O001 C17 C18 115.84(16) . . ?
C16 C17 O001 109.60(15) . . ?
C16 C17 C18 134.51(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O002 C19 C16 121.3(2) . . ?
O002 C19 C20 121.05(19) . . ?
C16 C19 C20 117.66(19) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O001 C14 C13 C5 68.2(2) . . . . ?
O001 C14 C13 C8 -48.5(2) . . . . ?
O001 C14 C15 C16 -0.5(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C5 C6 C4 0.3(3) . . . . ?
C1 C5 C6 C7 179.60(17) . . . . ?
C5 C1 C2 C3 0.7(4) . . . . ?
C5 C6 C4 C3 0.3(3) . . . . ?
C6 C4 C3 C2 -0.4(4) . . . . ?
C6 C5 C1 C2 -0.8(3) . . . . ?
C6 C7 C12 C11 177.4(2) . . . . ?
C7 C6 C4 C3 -178.8(2) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C7 C8 C13 C5 -1.41(18) . . . . ?
C7 C8 C13 C14 121.48(17) . . . . ?
C7 C12 C11 C10 -0.6(3) . . . . ?
C8 C7 C6 C4 178.6(2) . . . . ?
C8 C7 C6 C5 -0.5(2) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C8 C13 C5 C1 -178.93(19) . . . . ?
C8 C13 C5 C6 1.07(19) . . . . ?
C9 C8 C7 C6 -176.90(17) . . . . ?
C9 C8 C7 C12 2.0(3) . . . . ?
C9 C8 C13 C5 176.55(18) . . . . ?
C9 C8 C13 C14 -60.6(3) . . . . ?
C9 C10 C11 C12 1.8(4) . . . . ?
C12 C7 C6 C4 -0.2(4) . . . . ?
C12 C7 C6 C5 -179.3(2) . . . . ?
C13 C5 C1 C2 179.19(19) . . . . ?
C13 C5 C6 C4 -179.68(18) . . . . ?
C13 C5 C6 C7 -0.4(2) . . . . ?
C13 C8 C7 C6 1.3(2) . . . . ?
C13 C8 C7 C12 -179.80(17) . . . . ?
C13 C8 C9 C10 -178.66(18) . . . . ?
C13 C14 C15 C16 175.3(2) . . . . ?
C14 O001 C17 C16 0.3(2) . . . . ?
C14 O001 C17 C18 -177.60(16) . . . . ?
C14 C13 C5 C1 57.0(3) . . . . ?
C14 C13 C5 C6 -123.04(17) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C14 C15 C16 C19 -179.70(19) . . . . ?
C15 C14 C13 C5 -107.3(3) . . . . ?
C15 C14 C13 C8 136.0(2) . . . . ?
C15 C16 C17 O001 -0.6(2) . . . . ?
C15 C16 C17 C18 176.8(2) . . . . ?
C15 C16 C19 O002 171.2(2) . . . . ?
C15 C16 C19 C20 -8.9(3) . . . . ?
C17 O001 C14 C13 -176.48(16) . . . . ?
C17 O001 C14 C15 0.1(2) . . . . ?
C17 C16 C19 O002 -9.2(3) . . . . ?
C17 C16 C19 C20 170.7(2) . . . . ?
C19 C16 C17 O001 179.77(17) . . . . ?
C19 C16 C17 C18 -2.9(3) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
