# Supplementary Information (SI) for RSC Advances.
# 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_KHB05008
_database_code_depnum_ccdc_archive 'CCDC 2419735'
loop_
_audit_author_name
_audit_author_address
'Seojung Han'
;KIST
South Korea
;
_audit_update_record             
;
2025-01-26 deposited with the CCDC.	2025-05-02 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_weight         314.38
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.8617(7)
_cell_length_b                   6.9703(4)
_cell_length_c                   27.1759(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.016(3)
_cell_angle_gamma                90.0000
_cell_volume                     1653.04(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9562
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664.00
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.984

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15637
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.020
_diffrn_reflns_theta_full        27.470
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3778
_reflns_number_gt                2088
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1391
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3778
_refine_ls_number_parameters     225
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1014P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.81324(15) 0.52042(16) 0.41564(5) 0.0474(4) Uani 1 1 d . . .
O2 O 0.97251(15) 0.2023(2) 0.45603(6) 0.0609(4) Uani 1 1 d . . .
C1 C 0.7395(2) 0.3844(2) 0.44296(6) 0.0397(4) Uani 1 1 d . . .
C2 C 0.8343(2) 0.2000(3) 0.45376(7) 0.0438(4) Uani 1 1 d . . .
C3 C 0.7509(2) 0.0285(3) 0.46429(8) 0.0523(5) Uani 1 1 d . . .
C4 C 0.5985(2) 0.0206(3) 0.45185(8) 0.0507(5) Uani 1 1 d . . .
C5 C 0.5044(2) 0.1768(3) 0.42809(6) 0.0432(4) Uani 1 1 d . . .
C6 C 0.3466(2) 0.1536(3) 0.41167(7) 0.0547(5) Uani 1 1 d . . .
H6 H 0.2994 0.0390 0.4178 0.066 Uiso 1 1 calc R . .
C7 C 0.2614(2) 0.2995(4) 0.38658(8) 0.0637(6) Uani 1 1 d . . .
H7 H 0.1564 0.2843 0.3761 0.076 Uiso 1 1 calc R . .
C8 C 0.3319(2) 0.4682(3) 0.37704(8) 0.0618(6) Uani 1 1 d . . .
H8 H 0.2746 0.5650 0.3591 0.074 Uiso 1 1 calc R . .
C9 C 0.4859(2) 0.4953(3) 0.39373(7) 0.0515(5) Uani 1 1 d . . .
H9 H 0.5316 0.6109 0.3875 0.062 Uiso 1 1 calc R . .
C10 C 0.5738(2) 0.3510(2) 0.41979(6) 0.0397(4) Uani 1 1 d . . .
C11 C 0.7446(2) 0.4781(3) 0.49452(7) 0.0530(5) Uani 1 1 d . . .
H11A H 0.6909 0.5983 0.4906 0.064 Uiso 1 1 calc R . .
H11B H 0.8493 0.5000 0.5098 0.064 Uiso 1 1 calc R . .
H11C H 0.6969 0.3947 0.5154 0.064 Uiso 1 1 calc R . .
C12 C 0.8445(2) 0.4732(2) 0.36909(7) 0.0409(4) Uani 1 1 d . . .
C13 C 0.7975(2) 0.2991(3) 0.34478(7) 0.0477(5) Uani 1 1 d . . .
H13 H 0.7406 0.2116 0.3598 0.057 Uiso 1 1 calc R . .
C14 C 0.8350(2) 0.2590(3) 0.29961(7) 0.0536(5) Uani 1 1 d . . .
H14 H 0.8035 0.1435 0.2840 0.064 Uiso 1 1 calc R . .
C15 C 0.9204(2) 0.3882(3) 0.27598(7) 0.0542(5) Uani 1 1 d . . .
C16 C 0.9625(3) 0.3450(4) 0.22908(8) 0.0759(7) Uani 1 1 d . . .
H16 H 0.9334 0.2285 0.2136 0.091 Uiso 1 1 calc R . .
C17 C 1.0445(3) 0.4714(5) 0.20672(10) 0.0946(10) Uani 1 1 d . . .
H17 H 1.0712 0.4417 0.1760 0.113 Uiso 1 1 calc R . .
C18 C 1.0895(3) 0.6481(5) 0.22995(10) 0.0910(9) Uani 1 1 d . . .
H18 H 1.1465 0.7338 0.2144 0.109 Uiso 1 1 calc R . .
C19 C 1.0507(3) 0.6956(4) 0.27487(9) 0.0709(7) Uani 1 1 d . . .
H19 H 1.0801 0.8139 0.2893 0.085 Uiso 1 1 calc R . .
C20 C 0.9658(2) 0.5659(3) 0.29988(7) 0.0515(5) Uani 1 1 d . . .
C21 C 0.9264(2) 0.6075(3) 0.34750(7) 0.0452(5) Uani 1 1 d . . .
C22 C 0.9740(3) 0.7908(3) 0.37495(9) 0.0666(6) Uani 1 1 d . . .
H22A H 1.0373 0.7617 0.4065 0.080 Uiso 1 1 calc R . .
H22B H 0.8846 0.8593 0.3806 0.080 Uiso 1 1 calc R . .
H22C H 1.0306 0.8685 0.3554 0.080 Uiso 1 1 calc R . .
H3 H 0.817(3) -0.078(3) 0.4782(8) 0.068(6) Uiso 1 1 d . . .
H4 H 0.539(2) -0.098(3) 0.4568(7) 0.057(6) Uiso 1 1 d . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C12 1.381(2) . ?
O1 C1 1.430(2) . ?
O2 C2 1.215(2) . ?
C1 C10 1.512(2) . ?
C1 C2 1.536(3) . ?
C1 C11 1.540(2) . ?
C2 C3 1.460(3) . ?
C3 C4 1.335(3) . ?
C3 H3 0.98(2) . ?
C4 C5 1.453(3) . ?
C4 H4 1.00(2) . ?
C5 C10 1.397(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C21 1.376(2) . ?
C12 C13 1.409(3) . ?
C13 C14 1.356(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.402(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.421(3) . ?
C15 C20 1.423(3) . ?
C16 C17 1.351(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.410(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.423(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.428(3) . ?
C21 C22 1.503(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C12 O1 C1 120.01(13) . . ?
O1 C1 C10 112.59(14) . . ?
O1 C1 C2 111.70(13) . . ?
C10 C1 C2 114.22(13) . . ?
O1 C1 C11 104.32(14) . . ?
C10 C1 C11 108.49(14) . . ?
C2 C1 C11 104.64(15) . . ?
O2 C2 C3 122.74(17) . . ?
O2 C2 C1 120.76(16) . . ?
C3 C2 C1 116.36(15) . . ?
C4 C3 C2 120.55(18) . . ?
C4 C3 H3 125.4(13) . . ?
C2 C3 H3 113.8(13) . . ?
C3 C4 C5 123.99(17) . . ?
C3 C4 H4 122.3(12) . . ?
C5 C4 H4 113.7(12) . . ?
C10 C5 C6 119.45(18) . . ?
C10 C5 C4 119.24(17) . . ?
C6 C5 C4 121.27(18) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.37(19) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 119.25(17) . . ?
C9 C10 C1 121.25(16) . . ?
C5 C10 C1 119.30(15) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C12 O1 115.65(16) . . ?
C21 C12 C13 121.36(17) . . ?
O1 C12 C13 122.99(15) . . ?
C14 C13 C12 120.20(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.27(19) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 C20 118.82(17) . . ?
C16 C15 C20 119.7(2) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 117.77(19) . . ?
C19 C20 C21 122.5(2) . . ?
C15 C20 C21 119.74(17) . . ?
C12 C21 C20 118.58(17) . . ?
C12 C21 C22 119.35(17) . . ?
C20 C21 C22 122.06(17) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C12 O1 C1 C10 -69.87(19) . . . . ?
C12 O1 C1 C2 60.2(2) . . . . ?
C12 O1 C1 C11 172.69(15) . . . . ?
O1 C1 C2 O2 25.8(2) . . . . ?
C10 C1 C2 O2 155.02(16) . . . . ?
C11 C1 C2 O2 -86.5(2) . . . . ?
O1 C1 C2 C3 -158.20(16) . . . . ?
C10 C1 C2 C3 -29.0(2) . . . . ?
C11 C1 C2 C3 89.52(19) . . . . ?
O2 C2 C3 C4 -166.49(19) . . . . ?
C1 C2 C3 C4 17.6(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C10 -3.6(3) . . . . ?
C3 C4 C5 C6 173.89(19) . . . . ?
C10 C5 C6 C7 1.5(3) . . . . ?
C4 C5 C6 C7 -176.06(18) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -2.1(3) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C5 1.1(3) . . . . ?
C8 C9 C10 C1 -173.78(17) . . . . ?
C6 C5 C10 C9 -2.4(3) . . . . ?
C4 C5 C10 C9 175.16(16) . . . . ?
C6 C5 C10 C1 172.59(15) . . . . ?
C4 C5 C10 C1 -9.8(2) . . . . ?
O1 C1 C10 C9 -30.8(2) . . . . ?
C2 C1 C10 C9 -159.57(16) . . . . ?
C11 C1 C10 C9 84.2(2) . . . . ?
O1 C1 C10 C5 154.32(15) . . . . ?
C2 C1 C10 C5 25.5(2) . . . . ?
C11 C1 C10 C5 -90.74(19) . . . . ?
C1 O1 C12 C21 -175.07(15) . . . . ?
C1 O1 C12 C13 4.6(3) . . . . ?
C21 C12 C13 C14 1.3(3) . . . . ?
O1 C12 C13 C14 -178.38(17) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 178.8(2) . . . . ?
C13 C14 C15 C20 -1.0(3) . . . . ?
C14 C15 C16 C17 179.8(2) . . . . ?
C20 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C18 C19 C20 C15 -1.3(3) . . . . ?
C18 C19 C20 C21 178.3(2) . . . . ?
C14 C15 C20 C19 -179.23(19) . . . . ?
C16 C15 C20 C19 1.0(3) . . . . ?
C14 C15 C20 C21 1.2(3) . . . . ?
C16 C15 C20 C21 -178.65(18) . . . . ?
O1 C12 C21 C20 178.55(15) . . . . ?
C13 C12 C21 C20 -1.1(3) . . . . ?
O1 C12 C21 C22 -0.3(3) . . . . ?
C13 C12 C21 C22 -179.94(18) . . . . ?
C19 C20 C21 C12 -179.69(18) . . . . ?
C15 C20 C21 C12 -0.1(3) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C15 C20 C21 C22 178.69(19) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
