# Supplementary Information (SI) for Chemical Science.
# 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. 
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#######################################################################

data_A23045O_014
_database_code_depnum_ccdc_archive 'CCDC 2403461'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Korea Advanced Institute of Science and Technology (KAIST)
South Korea
;
_audit_update_record             
;
2024-11-18 deposited with the CCDC.	2025-04-25 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         'C24 H28 O4, 0.5(C6 H14)'
_chemical_formula_sum            'C27 H35 O4'
_chemical_formula_weight         423.55

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'

_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                   14.2241(7)
_cell_length_b                   11.8676(6)
_cell_length_c                   14.8052(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.4768(16)
_cell_angle_gamma                90
_cell_volume                     2325.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      26.03

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Ius 3.0 microfocus source'
_diffrn_measurement_device_type  'PHOTON II CPAD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22839
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.957
_diffrn_reflns_theta_max         26.051
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4578
_reflns_number_gt                3043
_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 software'
_computing_cell_refinement       'Bruker APEX4 software'
_computing_data_reduction        'Bruker APEX4 software'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0390P)²+0.6885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4578
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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 0.66344(11) 0.54968(13) -0.00362(10) 0.0368(4) Uani 1 1 d . . . . .
C2 C 0.71359(14) 0.52946(16) 0.08158(14) 0.0262(4) Uani 1 1 d . . . . .
C3 C 0.80877(14) 0.59160(15) 0.13578(14) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.83878(15) 0.67695(16) 0.08674(14) 0.0290(4) Uani 1 1 d . . . . .
H4 H 0.798243 0.694379 0.021410 0.035 Uiso 1 1 calc R U . . .
C5 C 0.92741(16) 0.73599(17) 0.13326(16) 0.0324(5) Uani 1 1 d . . . . .
C6 C 0.98751(16) 0.71111(17) 0.22950(16) 0.0324(5) Uani 1 1 d . . . . .
C7 C 0.95531(15) 0.62702(16) 0.27723(14) 0.0286(4) Uani 1 1 d . . . . .
H7 H 0.995267 0.610952 0.343006 0.034 Uiso 1 1 calc R U . . .
C8 C 0.86646(14) 0.56518(15) 0.23226(13) 0.0245(4) Uani 1 1 d . . . . .
C9 C 0.82940(14) 0.47250(15) 0.28341(13) 0.0242(4) Uani 1 1 d . . . . .
C10 C 0.73458(14) 0.51844(15) 0.29696(13) 0.0233(4) Uani 1 1 d . . . . .
C11 C 0.72481(14) 0.57532(15) 0.37571(13) 0.0258(4) Uani 1 1 d . . . . .
H11 H 0.782308 0.589964 0.432504 0.031 Uiso 1 1 calc R U . . .
C12 C 0.62947(15) 0.60994(16) 0.36923(13) 0.0277(4) Uani 1 1 d . . . . .
C13 C 0.54454(14) 0.59101(16) 0.28393(14) 0.0275(4) Uani 1 1 d . . . . .
C14 C 0.55530(14) 0.53670(15) 0.20516(13) 0.0259(4) Uani 1 1 d . . . . .
H14 H 0.498703 0.524913 0.146942 0.031 Uiso 1 1 calc R U . . .
C15 C 0.65112(14) 0.49999(14) 0.21370(13) 0.0234(4) Uani 1 1 d . . . . .
C16 C 0.68250(14) 0.43865(15) 0.13853(13) 0.0249(4) Uani 1 1 d . . . . .
C17 C 0.78080(14) 0.38082(15) 0.20541(14) 0.0264(4) Uani 1 1 d . . . . .
H17A H 0.825202 0.361708 0.169454 0.032 Uiso 1 1 calc R U . . .
H17B H 0.765964 0.311507 0.234954 0.032 Uiso 1 1 calc R U . . .
O18 O 0.96375(12) 0.81931(13) 0.09041(12) 0.0441(4) Uani 1 1 d . . . . .
C19 C 0.9005(2) 0.8572(2) -0.00323(18) 0.0476(6) Uani 1 1 d . . . . .
H19A H 0.933200 0.920038 -0.023150 0.071 Uiso 1 1 calc R U . . .
H19B H 0.835651 0.882337 -0.001207 0.071 Uiso 1 1 calc R U . . .
H19C H 0.888956 0.795320 -0.049892 0.071 Uiso 1 1 calc R U . . .
C20 C 1.08537(18) 0.7720(2) 0.27974(18) 0.0461(6) Uani 1 1 d . . . . .
H20A H 1.109501 0.756157 0.349510 0.069 Uiso 1 1 calc R U . . .
H20B H 1.074763 0.853244 0.269005 0.069 Uiso 1 1 calc R U . . .
H20C H 1.135714 0.746290 0.253506 0.069 Uiso 1 1 calc R U . . .
C21 C 0.91101(15) 0.42739(17) 0.37723(14) 0.0288(4) Uani 1 1 d . . . . .
H21 H 0.938316 0.492972 0.421514 0.035 Uiso 1 1 calc R U . . .
C22 C 0.99922(16) 0.37259(19) 0.35835(17) 0.0394(5) Uani 1 1 d . . . . .
H22A H 1.051972 0.352044 0.420332 0.059 Uiso 1 1 calc R U . . .
H22B H 1.026773 0.425806 0.323829 0.059 Uiso 1 1 calc R U . . .
H22C H 0.975508 0.304758 0.318776 0.059 Uiso 1 1 calc R U . . .
C23 C 0.86865(17) 0.34285(19) 0.43058(16) 0.0409(5) Uani 1 1 d . . . . .
H23A H 0.922512 0.319098 0.490758 0.061 Uiso 1 1 calc R U . . .
H23B H 0.842157 0.276991 0.389119 0.061 Uiso 1 1 calc R U . . .
H23C H 0.814153 0.378342 0.446030 0.061 Uiso 1 1 calc R U . . .
O24 O 0.60811(11) 0.66272(14) 0.44188(10) 0.0388(4) Uani 1 1 d . . . . .
C25 C 0.68846(18) 0.6799(2) 0.53140(17) 0.0483(6) Uani 1 1 d . . . . .
H25A H 0.662018 0.711544 0.578486 0.073 Uiso 1 1 calc R U . . .
H25B H 0.737448 0.732293 0.522197 0.073 Uiso 1 1 calc R U . . .
H25C H 0.721654 0.607763 0.555635 0.073 Uiso 1 1 calc R U . . .
O26 O 0.45493(11) 0.62884(14) 0.28727(10) 0.0375(4) Uani 1 1 d . . . . .
C27 C 0.36824(15) 0.6168(2) 0.20130(16) 0.0397(5) Uani 1 1 d . . . . .
H27A H 0.309084 0.647030 0.212050 0.060 Uiso 1 1 calc R U . . .
H27B H 0.357354 0.536799 0.184149 0.060 Uiso 1 1 calc R U . . .
H27C H 0.378395 0.658141 0.148312 0.060 Uiso 1 1 calc R U . . .
C28 C 0.60325(15) 0.35895(17) 0.07255(14) 0.0312(4) Uani 1 1 d . . . . .
H28A H 0.587669 0.300657 0.111831 0.047 Uiso 1 1 calc R U . . .
H28B H 0.629275 0.323482 0.026639 0.047 Uiso 1 1 calc R U . . .
H28C H 0.541760 0.401359 0.036662 0.047 Uiso 1 1 calc R U . . .
C31 C 0.1577(11) 0.4244(11) 0.2047(10) 0.067(4) Uani 0.555(7) 1 d . . P A 1
H31A H 0.227918 0.440879 0.245669 0.100 Uiso 0.555(7) 1 calc R U P A 1
H31B H 0.151456 0.344666 0.186170 0.100 Uiso 0.555(7) 1 calc R U P A 1
H31C H 0.113615 0.440803 0.240690 0.100 Uiso 0.555(7) 1 calc R U P A 1
C32 C 0.1263(4) 0.4984(4) 0.1122(4) 0.0428(14) Uani 0.555(7) 1 d . . P A 1
H32A H 0.129245 0.579040 0.130151 0.051 Uiso 0.555(7) 1 calc R U P A 1
H32B H 0.173130 0.485771 0.077567 0.051 Uiso 0.555(7) 1 calc R U P A 1
C33 C 0.0187(5) 0.4669(6) 0.0466(6) 0.040(2) Uani 0.555(7) 1 d . . P A 1
H33A H 0.016479 0.385606 0.031136 0.048 Uiso 0.555(7) 1 calc R U P A 1
H33B H -0.027178 0.480085 0.082213 0.048 Uiso 0.555(7) 1 calc R U P A 1
C34 C 0.1652(15) 0.4308(17) 0.2090(13) 0.094(8) Uani 0.445(7) 1 d . . P A 2
H34A H 0.169767 0.378425 0.261646 0.142 Uiso 0.445(7) 1 calc R U P A 2
H34B H 0.177396 0.507776 0.234551 0.142 Uiso 0.445(7) 1 calc R U P A 2
H34C H 0.215864 0.410755 0.181352 0.142 Uiso 0.445(7) 1 calc R U P A 2
C35 C 0.0517(5) 0.4230(5) 0.1241(5) 0.054(2) Uani 0.445(7) 1 d . . P A 2
H35A H 0.037794 0.345122 0.098625 0.065 Uiso 0.445(7) 1 calc R U P A 2
H35B H -0.000217 0.444393 0.150813 0.065 Uiso 0.445(7) 1 calc R U P A 2
C36 C 0.0495(7) 0.5023(8) 0.0451(8) 0.051(3) Uani 0.445(7) 1 d . . P A 2
H36A H 0.106898 0.484707 0.024858 0.062 Uiso 0.445(7) 1 calc R U P A 2
H36B H 0.059081 0.579999 0.071224 0.062 Uiso 0.445(7) 1 calc R U P A 2


_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 C2 1.224(2) . ?
C2 C3 1.492(3) . ?
C2 C16 1.530(3) . ?
C3 C8 1.398(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 O18 1.374(3) . ?
C5 C6 1.399(3) . ?
C6 C7 1.394(3) . ?
C6 C20 1.502(3) . ?
C7 C8 1.401(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.534(3) . ?
C9 C10 1.534(3) . ?
C9 C21 1.544(3) . ?
C9 C17 1.553(3) . ?
C10 C15 1.380(3) . ?
C10 C11 1.398(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 O24 1.371(2) . ?
C12 C13 1.410(3) . ?
C13 O26 1.369(2) . ?
C13 C14 1.389(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.527(3) . ?
C16 C28 1.521(3) . ?
C16 C17 1.547(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
O18 C19 1.421(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.527(3) . ?
C21 C23 1.530(3) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O24 C25 1.413(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O26 C27 1.418(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C31 C32 1.548(14) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.528(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C33 1.505(16) 3_565 ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.65(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.492(12) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C36 1.55(2) 3_565 ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
O1 C2 C3 121.94(18) . . ?
O1 C2 C16 121.94(17) . . ?
C3 C2 C16 116.12(16) . . ?
C8 C3 C4 121.04(18) . . ?
C8 C3 C2 121.09(17) . . ?
C4 C3 C2 117.87(17) . . ?
C5 C4 C3 120.17(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O18 C5 C4 124.2(2) . . ?
O18 C5 C6 115.43(18) . . ?
C4 C5 C6 120.35(18) . . ?
C7 C6 C5 118.42(19) . . ?
C7 C6 C20 120.7(2) . . ?
C5 C6 C20 120.87(19) . . ?
C6 C7 C8 122.74(19) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C3 C8 C7 117.26(17) . . ?
C3 C8 C9 119.08(16) . . ?
C7 C8 C9 123.65(17) . . ?
C8 C9 C10 106.69(15) . . ?
C8 C9 C21 114.31(15) . . ?
C10 C9 C21 114.40(16) . . ?
C8 C9 C17 105.97(15) . . ?
C10 C9 C17 99.96(15) . . ?
C21 C9 C17 114.18(15) . . ?
C15 C10 C11 120.39(18) . . ?
C15 C10 C9 109.68(16) . . ?
C11 C10 C9 129.89(17) . . ?
C12 C11 C10 118.62(17) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
O24 C12 C11 124.96(17) . . ?
O24 C12 C13 114.34(17) . . ?
C11 C12 C13 120.69(17) . . ?
O26 C13 C14 124.93(18) . . ?
O26 C13 C12 114.78(17) . . ?
C14 C13 C12 120.29(18) . . ?
C13 C14 C15 118.31(17) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C10 C15 C14 121.67(17) . . ?
C10 C15 C16 109.94(16) . . ?
C14 C15 C16 128.38(17) . . ?
C28 C16 C15 114.77(16) . . ?
C28 C16 C2 112.32(16) . . ?
C15 C16 C2 106.65(15) . . ?
C28 C16 C17 114.76(15) . . ?
C15 C16 C17 100.48(14) . . ?
C2 C16 C17 106.82(15) . . ?
C16 C17 C9 102.54(14) . . ?
C16 C17 H17A 111.3 . . ?
C9 C17 H17A 111.3 . . ?
C16 C17 H17B 111.3 . . ?
C9 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C5 O18 C19 117.85(18) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C23 108.69(18) . . ?
C22 C21 C9 112.37(17) . . ?
C23 C21 C9 112.53(16) . . ?
C22 C21 H21 107.7 . . ?
C23 C21 H21 107.7 . . ?
C9 C21 H21 107.7 . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 O24 C25 117.80(16) . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C13 O26 C27 116.70(16) . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C16 C28 H28A 109.5 . . ?
C16 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C16 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C31 108.7(7) . . ?
C33 C32 H32A 109.9 . . ?
C31 C32 H32A 109.9 . . ?
C33 C32 H32B 109.9 . . ?
C31 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
C33 C33 C32 113.0(7) 3_565 . ?
C33 C33 H33A 109.0 3_565 . ?
C32 C33 H33A 109.0 . . ?
C33 C33 H33B 109.0 3_565 . ?
C32 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C35 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C34 107.2(7) . . ?
C36 C35 H35A 110.3 . . ?
C34 C35 H35A 110.3 . . ?
C36 C35 H35B 110.3 . . ?
C34 C35 H35B 110.3 . . ?
H35A C35 H35B 108.5 . . ?
C35 C36 C36 114.0(10) . 3_565 ?
C35 C36 H36A 108.8 . . ?
C36 C36 H36A 108.8 3_565 . ?
C35 C36 H36B 108.8 . . ?
C36 C36 H36B 108.8 3_565 . ?
H36A C36 H36B 107.7 . . ?

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
O1 C2 C3 C8 -178.22(18) . . . . ?
C16 C2 C3 C8 1.5(3) . . . . ?
O1 C2 C3 C4 1.5(3) . . . . ?
C16 C2 C3 C4 -178.77(16) . . . . ?
C8 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 C5 -178.96(17) . . . . ?
C3 C4 C5 O18 178.65(18) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
O18 C5 C6 C7 -179.71(18) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
O18 C5 C6 C20 -0.8(3) . . . . ?
C4 C5 C6 C20 178.07(19) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C20 C6 C7 C8 -177.65(19) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
C2 C3 C8 C7 179.34(17) . . . . ?
C4 C3 C8 C9 178.87(17) . . . . ?
C2 C3 C8 C9 -1.4(3) . . . . ?
C6 C7 C8 C3 -0.7(3) . . . . ?
C6 C7 C8 C9 -179.83(18) . . . . ?
C3 C8 C9 C10 -68.9(2) . . . . ?
C7 C8 C9 C10 110.23(19) . . . . ?
C3 C8 C9 C21 163.58(16) . . . . ?
C7 C8 C9 C21 -17.3(3) . . . . ?
C3 C8 C9 C17 36.9(2) . . . . ?
C7 C8 C9 C17 -143.90(18) . . . . ?
C8 C9 C10 C15 84.59(18) . . . . ?
C21 C9 C10 C15 -147.98(16) . . . . ?
C17 C9 C10 C15 -25.55(19) . . . . ?
C8 C9 C10 C11 -93.0(2) . . . . ?
C21 C9 C10 C11 34.4(3) . . . . ?
C17 C9 C10 C11 156.86(19) . . . . ?
C15 C10 C11 C12 1.7(3) . . . . ?
C9 C10 C11 C12 179.03(18) . . . . ?
C10 C11 C12 O24 177.49(18) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
O24 C12 C13 O26 0.4(3) . . . . ?
C11 C12 C13 O26 179.70(17) . . . . ?
O24 C12 C13 C14 -179.02(17) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
O26 C13 C14 C15 -178.06(18) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C11 C10 C15 C14 -0.1(3) . . . . ?
C9 C10 C15 C14 -177.94(16) . . . . ?
C11 C10 C15 C16 178.86(16) . . . . ?
C9 C10 C15 C16 1.0(2) . . . . ?
C13 C14 C15 C10 -1.4(3) . . . . ?
C13 C14 C15 C16 179.88(17) . . . . ?
C10 C15 C16 C28 147.79(17) . . . . ?
C14 C15 C16 C28 -33.4(3) . . . . ?
C10 C15 C16 C2 -87.14(18) . . . . ?
C14 C15 C16 C2 91.7(2) . . . . ?
C10 C15 C16 C17 24.12(19) . . . . ?
C14 C15 C16 C17 -157.03(18) . . . . ?
O1 C2 C16 C28 15.6(3) . . . . ?
C3 C2 C16 C28 -164.14(16) . . . . ?
O1 C2 C16 C15 -110.9(2) . . . . ?
C3 C2 C16 C15 69.3(2) . . . . ?
O1 C2 C16 C17 142.28(18) . . . . ?
C3 C2 C16 C17 -37.5(2) . . . . ?
C28 C16 C17 C9 -162.64(16) . . . . ?
C15 C16 C17 C9 -38.97(17) . . . . ?
C2 C16 C17 C9 72.15(17) . . . . ?
C8 C9 C17 C16 -71.33(18) . . . . ?
C10 C9 C17 C16 39.37(17) . . . . ?
C21 C9 C17 C16 161.95(16) . . . . ?
C4 C5 O18 C19 8.3(3) . . . . ?
C6 C5 O18 C19 -172.87(19) . . . . ?
C8 C9 C21 C22 -62.0(2) . . . . ?
C10 C9 C21 C22 174.57(16) . . . . ?
C17 C9 C21 C22 60.3(2) . . . . ?
C8 C9 C21 C23 174.91(17) . . . . ?
C10 C9 C21 C23 51.5(2) . . . . ?
C17 C9 C21 C23 -62.8(2) . . . . ?
C11 C12 O24 C25 -2.3(3) . . . . ?
C13 C12 O24 C25 177.0(2) . . . . ?
C14 C13 O26 C27 -3.8(3) . . . . ?
C12 C13 O26 C27 176.87(18) . . . . ?
C31 C32 C33 C33 -179.0(7) . . . 3_565 ?
C34 C35 C36 C36 174.9(11) . . . 3_565 ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044

























####################################################################### 
# 
# 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_A24243O_014
_database_code_depnum_ccdc_archive 'CCDC 2403466'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Korea Advanced Institute of Science and Technology (KAIST)
South Korea
;
_audit_update_record             
;
2024-11-18 deposited with the CCDC.	2025-04-25 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         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.050(5)
_cell_length_b                   15.376(6)
_cell_length_c                   7.436(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.521(14)
_cell_angle_gamma                90
_cell_volume                     1450.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4650
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Ius 3.0 microfocus source'
_diffrn_measurement_device_type  'PHOTON II CPAD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16296
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.649
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3149
_reflns_number_gt                1756
_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 APEX5 software'
_computing_cell_refinement       'Bruker APEX5 software'
_computing_data_reduction        'Bruker APEX5 software'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0314P)²+0.3495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3149
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.32301(18) 0.24558(14) 0.3692(3) 0.0475(6) Uani 1 1 d . . . . .
H1 H 0.297913 0.189443 0.377217 0.057 Uiso 1 1 calc R U . . .
C2 C 0.42665(18) 0.25822(14) 0.3655(3) 0.0479(6) Uani 1 1 d . . . . .
C3 C 0.46632(18) 0.34267(15) 0.3585(3) 0.0493(6) Uani 1 1 d . . . . .
C4 C 0.39672(18) 0.41114(14) 0.3482(3) 0.0487(6) Uani 1 1 d . . . . .
H4 H 0.422529 0.467219 0.342794 0.058 Uiso 1 1 calc R U . . .
C5 C 0.29008(17) 0.40138(13) 0.3453(3) 0.0413(5) Uani 1 1 d . . . . .
C6 C 0.25484(17) 0.31646(13) 0.3610(3) 0.0426(5) Uani 1 1 d . . . . .
O7 O 0.49891(13) 0.19309(11) 0.3711(3) 0.0631(5) Uani 1 1 d . . . . .
C8 C 0.4601(2) 0.10644(15) 0.3657(4) 0.0674(8) Uani 1 1 d . . . . .
H8A H 0.516563 0.066363 0.365998 0.101 Uiso 1 1 calc R U . . .
H8B H 0.405611 0.098338 0.255419 0.101 Uiso 1 1 calc R U . . .
H8C H 0.432013 0.096138 0.472167 0.101 Uiso 1 1 calc R U . . .
C9 C 0.5799(2) 0.35572(18) 0.3595(4) 0.0691(8) Uani 1 1 d . . . . .
H9A H 0.594089 0.416779 0.353547 0.104 Uiso 1 1 calc R U . . .
H9B H 0.595493 0.326940 0.254455 0.104 Uiso 1 1 calc R U . . .
H9C H 0.622996 0.331825 0.471037 0.104 Uiso 1 1 calc R U . . .
C10 C 0.14607(18) 0.29871(13) 0.3765(3) 0.0454(6) Uani 1 1 d . . . . .
O11 O 0.10989(14) 0.22533(10) 0.3655(3) 0.0639(5) Uani 1 1 d . . . . .
C12 C 0.08191(17) 0.37677(13) 0.4118(3) 0.0448(5) Uani 1 1 d . . . . .
O13 O 0.12381(14) 0.40504(10) 0.5977(2) 0.0542(4) Uani 1 1 d . . . . .
H13 H 0.121(2) 0.3673(19) 0.681(4) 0.081 Uiso 1 1 d . U . . .
C14 C -0.03379(19) 0.35425(16) 0.3813(4) 0.0619(7) Uani 1 1 d . . . . .
H14A H -0.059451 0.333052 0.257497 0.093 Uiso 1 1 calc R U . . .
H14B H -0.072661 0.405249 0.399232 0.093 Uiso 1 1 calc R U . . .
H14C H -0.042650 0.310163 0.467833 0.093 Uiso 1 1 calc R U . . .
C15 C 0.10155(17) 0.44980(13) 0.2875(3) 0.0475(6) Uani 1 1 d . . . . .
H15A H 0.057650 0.499082 0.301441 0.057 Uiso 1 1 calc R U . . .
H15B H 0.080909 0.430719 0.159749 0.057 Uiso 1 1 calc R U . . .
C16 C 0.21624(17) 0.47884(13) 0.3298(3) 0.0437(5) Uani 1 1 d . . . . .
H16 H 0.230865 0.506588 0.451773 0.052 Uiso 1 1 calc R U . . .
C17 C 0.23679(19) 0.54821(14) 0.1916(3) 0.0517(6) Uani 1 1 d . . . . .
H17 H 0.311378 0.564213 0.230904 0.062 Uiso 1 1 calc R U . . .
C18 C 0.2192(2) 0.51434(19) -0.0056(4) 0.0725(8) Uani 1 1 d . . . . .
H18A H 0.244290 0.556410 -0.080553 0.109 Uiso 1 1 calc R U . . .
H18B H 0.145272 0.504539 -0.054894 0.109 Uiso 1 1 calc R U . . .
H18C H 0.256811 0.460716 -0.005860 0.109 Uiso 1 1 calc R U . . .
C19 C 0.1734(2) 0.63095(15) 0.1989(5) 0.0712(8) Uani 1 1 d . . . . .
H19A H 0.195827 0.675400 0.125988 0.107 Uiso 1 1 calc R U . . .
H19B H 0.184526 0.650301 0.324784 0.107 Uiso 1 1 calc R U . . .
H19C H 0.099805 0.619221 0.150666 0.107 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 C2 1.373(3) . ?
C1 C6 1.399(3) . ?
C1 H1 0.9300 . ?
C2 O7 1.369(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.381(3) . ?
C3 C9 1.494(4) . ?
C4 C5 1.395(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 C16 1.519(3) . ?
C6 C10 1.476(3) . ?
O7 C8 1.422(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O11 1.219(3) . ?
C10 C12 1.521(3) . ?
C12 O13 1.430(3) . ?
C12 C14 1.514(4) . ?
C12 C15 1.514(3) . ?
O13 H13 0.86(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.523(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.547(3) . ?
C16 H16 0.9800 . ?
C17 C18 1.522(4) . ?
C17 C19 1.526(3) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
O7 C2 C1 124.8(2) . . ?
O7 C2 C3 114.9(2) . . ?
C1 C2 C3 120.4(2) . . ?
C4 C3 C2 117.6(2) . . ?
C4 C3 C9 122.5(2) . . ?
C2 C3 C9 119.9(2) . . ?
C3 C4 C5 124.0(2) . . ?
C3 C4 H4 118.0 . . ?
C5 C4 H4 118.0 . . ?
C4 C5 C6 116.46(19) . . ?
C4 C5 C16 121.98(19) . . ?
C6 C5 C16 121.55(19) . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 C10 121.34(19) . . ?
C1 C6 C10 117.76(19) . . ?
C2 O7 C8 116.49(19) . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O11 C10 C6 122.0(2) . . ?
O11 C10 C12 121.5(2) . . ?
C6 C10 C12 116.48(18) . . ?
O13 C12 C14 110.9(2) . . ?
O13 C12 C15 106.48(17) . . ?
C14 C12 C15 112.55(19) . . ?
O13 C12 C10 107.77(17) . . ?
C14 C12 C10 111.34(19) . . ?
C15 C12 C10 107.5(2) . . ?
C12 O13 H13 115(2) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 112.95(18) . . ?
C12 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C12 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C5 C16 C15 111.18(17) . . ?
C5 C16 C17 112.66(19) . . ?
C15 C16 C17 112.31(18) . . ?
C5 C16 H16 106.8 . . ?
C15 C16 H16 106.8 . . ?
C17 C16 H16 106.8 . . ?
C18 C17 C19 111.0(2) . . ?
C18 C17 C16 113.2(2) . . ?
C19 C17 C16 111.8(2) . . ?
C18 C17 H17 106.8 . . ?
C19 C17 H17 106.8 . . ?
C16 C17 H17 106.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 O7 -179.4(2) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
O7 C2 C3 C4 178.5(2) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
O7 C2 C3 C9 -0.6(3) . . . . ?
C1 C2 C3 C9 178.4(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C9 C3 C4 C5 179.4(2) . . . . ?
C3 C4 C5 C6 2.5(3) . . . . ?
C3 C4 C5 C16 -178.7(2) . . . . ?
C4 C5 C6 C1 -3.2(3) . . . . ?
C16 C5 C6 C1 177.9(2) . . . . ?
C4 C5 C6 C10 174.4(2) . . . . ?
C16 C5 C6 C10 -4.4(3) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C10 -176.5(2) . . . . ?
C1 C2 O7 C8 5.2(4) . . . . ?
C3 C2 O7 C8 -175.9(2) . . . . ?
C5 C6 C10 O11 170.0(2) . . . . ?
C1 C6 C10 O11 -12.3(3) . . . . ?
C5 C6 C10 C12 -11.4(3) . . . . ?
C1 C6 C10 C12 166.3(2) . . . . ?
O11 C10 C12 O13 107.3(2) . . . . ?
C6 C10 C12 O13 -71.3(2) . . . . ?
O11 C10 C12 C14 -14.5(3) . . . . ?
C6 C10 C12 C14 166.9(2) . . . . ?
O11 C10 C12 C15 -138.3(2) . . . . ?
C6 C10 C12 C15 43.2(3) . . . . ?
O13 C12 C15 C16 52.7(2) . . . . ?
C14 C12 C15 C16 174.5(2) . . . . ?
C10 C12 C15 C16 -62.6(2) . . . . ?
C4 C5 C16 C15 167.6(2) . . . . ?
C6 C5 C16 C15 -13.7(3) . . . . ?
C4 C5 C16 C17 40.5(3) . . . . ?
C6 C5 C16 C17 -140.7(2) . . . . ?
C12 C15 C16 C5 48.1(3) . . . . ?
C12 C15 C16 C17 175.35(19) . . . . ?
C5 C16 C17 C18 62.1(3) . . . . ?
C15 C16 C17 C18 -64.3(3) . . . . ?
C5 C16 C17 C19 -171.6(2) . . . . ?
C15 C16 C17 C19 61.9(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
O13 H13 O11 0.86(3) 2.00(3) 2.861(3) 177(3) 4_566 yes

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_A24108O_014
_database_code_depnum_ccdc_archive 'CCDC 2403465'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Korea Advanced Institute of Science and Technology (KAIST)
South Korea
;
_audit_update_record             
;
2024-11-18 deposited with the CCDC.	2025-04-25 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         'C22 H19 F3 O4'
_chemical_formula_sum            'C22 H19 F3 O4'
_chemical_formula_weight         404.37

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'
F F 0.0171 0.0103 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.6232(8)
_cell_length_b                   15.1691(17)
_cell_length_c                   18.739(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.374(4)
_cell_angle_gamma                90
_cell_volume                     1882.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6209
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Ius 3.0 microfocus source'
_diffrn_measurement_device_type  'PHOTON II CPAD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18598
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.556
_diffrn_reflns_theta_max         26.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3695
_reflns_number_gt                2414
_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 APEX5 software'
_computing_cell_refinement       'Bruker APEX5 software'
_computing_data_reduction        'Bruker APEX5 software'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0285P)²+0.4738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3695
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 -0.1413(3) 0.35948(12) 0.26703(10) 0.0464(4) Uani 1 1 d . . . . .
C2 C -0.0429(4) 0.42636(15) 0.27602(12) 0.0338(5) Uani 1 1 d . . . . .
C3 C -0.1280(4) 0.51359(17) 0.26172(13) 0.0405(6) Uani 1 1 d . . . . .
H3 H -0.258721 0.517704 0.239969 0.049 Uiso 1 1 calc R U . . .
C4 C -0.0293(4) 0.58730(17) 0.27805(13) 0.0428(6) Uani 1 1 d . . . . .
H4 H -0.090688 0.642141 0.266161 0.051 Uiso 1 1 calc R U . . .
C5 C 0.1686(4) 0.58778(15) 0.31332(12) 0.0359(5) Uani 1 1 d . . . . .
C6 C 0.2582(5) 0.66684(15) 0.33652(14) 0.0471(7) Uani 1 1 d . . . . .
H6 H 0.192823 0.721341 0.326457 0.056 Uiso 1 1 calc R U . . .
C7 C 0.4406(5) 0.66618(16) 0.37387(16) 0.0497(7) Uani 1 1 d . . . . .
H7 H 0.500032 0.719948 0.389712 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5352(4) 0.58766(17) 0.38791(15) 0.0471(6) Uani 1 1 d . . . . .
H8 H 0.659564 0.587193 0.414265 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4517(4) 0.50854(15) 0.36410(13) 0.0369(5) Uani 1 1 d . . . . .
H9 H 0.520710 0.454729 0.373523 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2684(3) 0.50754(14) 0.32672(11) 0.0289(5) Uani 1 1 d . . . . .
C11 C 0.1843(3) 0.42196(14) 0.29556(11) 0.0285(5) Uani 1 1 d . . . . .
C12 C 0.2839(4) 0.40917(14) 0.22188(11) 0.0330(5) Uani 1 1 d . . . . .
H12A H 0.430851 0.405315 0.228637 0.050 Uiso 1 1 calc R U . . .
H12B H 0.250371 0.459396 0.190914 0.050 Uiso 1 1 calc R U . . .
H12C H 0.233289 0.354738 0.199686 0.050 Uiso 1 1 calc R U . . .
C13 C 0.2257(3) 0.34436(13) 0.34518(11) 0.0274(5) Uani 1 1 d . . . . .
C14 C 0.1280(3) 0.34087(13) 0.41064(11) 0.0274(5) Uani 1 1 d . . . . .
O15 O -0.0021(2) 0.40936(10) 0.42351(8) 0.0350(4) Uani 1 1 d . . . . .
C16 C -0.1311(4) 0.40052(16) 0.48288(13) 0.0415(6) Uani 1 1 d . . . . .
H16A H -0.222765 0.451162 0.484472 0.062 Uiso 1 1 calc R U . . .
H16B H -0.049224 0.398181 0.527099 0.062 Uiso 1 1 calc R U . . .
H16C H -0.210059 0.346132 0.477898 0.062 Uiso 1 1 calc R U . . .
C17 C 0.1639(3) 0.27143(14) 0.45746(12) 0.0317(5) Uani 1 1 d . . . . .
H17 H 0.099477 0.270022 0.502193 0.038 Uiso 1 1 calc R U . . .
C18 C 0.2942(4) 0.20407(14) 0.43881(12) 0.0327(5) Uani 1 1 d . . . . .
H18 H 0.316120 0.156160 0.470712 0.039 Uiso 1 1 calc R U . . .
C19 C 0.3926(3) 0.20547(14) 0.37475(12) 0.0302(5) Uani 1 1 d . . . . .
C20 C 0.3570(3) 0.27677(14) 0.32882(12) 0.0288(5) Uani 1 1 d . . . . .
H20 H 0.425474 0.278872 0.284873 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5382(4) 0.13423(14) 0.35362(12) 0.0329(5) Uani 1 1 d . . . . .
H21A H 0.534274 0.128459 0.300986 0.039 Uiso 1 1 calc R U . . .
H21B H 0.493368 0.077437 0.373886 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7536(4) 0.15160(14) 0.37839(11) 0.0325(5) Uani 1 1 d . . . . .
H22A H 0.842783 0.105075 0.359645 0.039 Uiso 1 1 calc R U . . .
H22B H 0.798835 0.208952 0.359277 0.039 Uiso 1 1 calc R U . . .
O23 O 0.7702(2) 0.15293(9) 0.45649(8) 0.0318(4) Uani 1 1 d . . . . .
O24 O 0.7636(3) 0.00430(10) 0.46199(9) 0.0465(5) Uani 1 1 d . . . . .
C25 C 0.7733(3) 0.07591(14) 0.48826(12) 0.0329(5) Uani 1 1 d . . . . .
C26 C 0.7902(4) 0.08887(15) 0.56906(13) 0.0377(6) Uani 1 1 d . . . . .
F27 F 0.9318(3) 0.14704(10) 0.58800(8) 0.0516(4) Uani 1 1 d . . . . .
F28 F 0.6149(3) 0.11807(11) 0.59394(8) 0.0557(4) Uani 1 1 d . . . . .
F29 F 0.8325(3) 0.01373(10) 0.60187(8) 0.0515(4) Uani 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
O1 C2 1.216(3) . ?
C2 C3 1.461(3) . ?
C2 C11 1.541(3) . ?
C3 C4 1.327(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.454(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(4) . ?
C5 C10 1.405(3) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.369(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.523(3) . ?
C11 C13 1.521(3) . ?
C11 C12 1.557(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C20 1.384(3) . ?
C13 C14 1.401(3) . ?
C14 O15 1.375(3) . ?
C14 C17 1.388(3) . ?
O15 C16 1.425(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.399(3) . ?
C19 C21 1.508(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.513(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O23 1.465(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O23 C25 1.311(3) . ?
O24 C25 1.194(3) . ?
C25 C26 1.528(3) . ?
C26 F29 1.322(3) . ?
C26 F27 1.330(3) . ?
C26 F28 1.337(3) . ?

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
O1 C2 C3 121.8(2) . . ?
O1 C2 C11 120.9(2) . . ?
C3 C2 C11 117.0(2) . . ?
C4 C3 C2 122.3(2) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 122.9(2) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C6 C5 C10 119.4(2) . . ?
C6 C5 C4 121.0(2) . . ?
C10 C5 C4 119.5(2) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 118.9(2) . . ?
C9 C10 C11 120.7(2) . . ?
C5 C10 C11 120.2(2) . . ?
C13 C11 C10 111.50(19) . . ?
C13 C11 C2 109.83(18) . . ?
C10 C11 C2 113.57(18) . . ?
C13 C11 C12 111.84(17) . . ?
C10 C11 C12 106.70(17) . . ?
C2 C11 C12 103.10(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 C13 C14 118.2(2) . . ?
C20 C13 C11 122.88(18) . . ?
C14 C13 C11 118.96(19) . . ?
O15 C14 C17 124.15(19) . . ?
O15 C14 C13 115.44(18) . . ?
C17 C14 C13 120.4(2) . . ?
C14 O15 C16 117.12(17) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C14 119.86(19) . . ?
C18 C17 H17 120.1 . . ?
C14 C17 H17 120.1 . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 118.1(2) . . ?
C18 C19 C21 122.4(2) . . ?
C20 C19 C21 119.46(19) . . ?
C13 C20 C19 122.3(2) . . ?
C13 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C19 C21 C22 113.53(19) . . ?
C19 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
C19 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
O23 C22 C21 110.88(17) . . ?
O23 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
O23 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C25 O23 C22 116.18(17) . . ?
O24 C25 O23 128.6(2) . . ?
O24 C25 C26 121.8(2) . . ?
O23 C25 C26 109.58(19) . . ?
F29 C26 F27 107.9(2) . . ?
F29 C26 F28 107.44(19) . . ?
F27 C26 F28 107.5(2) . . ?
F29 C26 C25 111.1(2) . . ?
F27 C26 C25 112.60(19) . . ?
F28 C26 C25 110.2(2) . . ?

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
O1 C2 C3 C4 173.1(2) . . . . ?
C11 C2 C3 C4 -13.1(3) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C3 C4 C5 C6 -173.1(2) . . . . ?
C3 C4 C5 C10 4.6(3) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
C4 C5 C6 C7 176.0(2) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C8 C9 C10 C11 175.2(2) . . . . ?
C6 C5 C10 C9 1.4(3) . . . . ?
C4 C5 C10 C9 -176.3(2) . . . . ?
C6 C5 C10 C11 -173.84(19) . . . . ?
C4 C5 C10 C11 8.5(3) . . . . ?
C9 C10 C11 C13 38.1(3) . . . . ?
C5 C10 C11 C13 -146.77(19) . . . . ?
C9 C10 C11 C2 162.79(19) . . . . ?
C5 C10 C11 C2 -22.0(3) . . . . ?
C9 C10 C11 C12 -84.3(2) . . . . ?
C5 C10 C11 C12 90.9(2) . . . . ?
O1 C2 C11 C13 -36.6(3) . . . . ?
C3 C2 C11 C13 149.51(19) . . . . ?
O1 C2 C11 C10 -162.2(2) . . . . ?
C3 C2 C11 C10 23.9(3) . . . . ?
O1 C2 C11 C12 82.7(2) . . . . ?
C3 C2 C11 C12 -91.2(2) . . . . ?
C10 C11 C13 C20 -111.9(2) . . . . ?
C2 C11 C13 C20 121.3(2) . . . . ?
C12 C11 C13 C20 7.5(3) . . . . ?
C10 C11 C13 C14 67.7(3) . . . . ?
C2 C11 C13 C14 -59.1(3) . . . . ?
C12 C11 C13 C14 -172.9(2) . . . . ?
C20 C13 C14 O15 -179.4(2) . . . . ?
C11 C13 C14 O15 1.0(3) . . . . ?
C20 C13 C14 C17 0.3(3) . . . . ?
C11 C13 C14 C17 -179.3(2) . . . . ?
C17 C14 O15 C16 -10.7(3) . . . . ?
C13 C14 O15 C16 169.0(2) . . . . ?
O15 C14 C17 C18 178.3(2) . . . . ?
C13 C14 C17 C18 -1.3(3) . . . . ?
C14 C17 C18 C19 1.2(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C17 C18 C19 C21 178.7(2) . . . . ?
C14 C13 C20 C19 0.8(3) . . . . ?
C11 C13 C20 C19 -179.5(2) . . . . ?
C18 C19 C20 C13 -0.9(4) . . . . ?
C21 C19 C20 C13 -179.8(2) . . . . ?
C18 C19 C21 C22 -88.8(3) . . . . ?
C20 C19 C21 C22 90.1(3) . . . . ?
C19 C21 C22 O23 63.6(2) . . . . ?
C21 C22 O23 C25 78.4(2) . . . . ?
C22 O23 C25 O24 -0.3(4) . . . . ?
C22 O23 C25 C26 -179.79(18) . . . . ?
O24 C25 C26 F29 12.5(3) . . . . ?
O23 C25 C26 F29 -168.0(2) . . . . ?
O24 C25 C26 F27 133.7(2) . . . . ?
O23 C25 C26 F27 -46.8(3) . . . . ?
O24 C25 C26 F28 -106.4(3) . . . . ?
O23 C25 C26 F28 73.1(2) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.047

























####################################################################### 
# 
# 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_A24110O_002
_database_code_depnum_ccdc_archive 'CCDC 2403468'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;Korea Advanced Institute of Science and Technology (KAIST)
South Korea
;
_audit_update_record             
;
2024-11-18 deposited with the CCDC.	2025-04-25 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         'C22 H24 O3, C H Cl3'
_chemical_formula_sum            'C23 H25 Cl3 O3'
_chemical_formula_weight         455.78

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.6471(16)
_cell_length_b                   11.616(2)
_cell_length_c                   11.779(2)
_cell_angle_alpha                91.132(6)
_cell_angle_beta                 107.559(6)
_cell_angle_gamma                99.486(6)
_cell_volume                     1109.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.00

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.435
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Ius 3.0 microfocus source'
_diffrn_measurement_device_type  'PHOTON II CPAD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26489
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         27.001
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4774
_reflns_number_gt                3263
_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 APEX5 software'
_computing_cell_refinement       'Bruker APEX5 software'
_computing_data_reduction        'Bruker APEX5 software'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0421P)²+1.0044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4774
_refine_ls_number_parameters     307
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.035
_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 0.3375(2) 0.15093(15) 0.72355(17) 0.0356(4) Uani 1 1 d . . . . .
C2 C 0.4460(3) 0.2373(2) 0.7354(2) 0.0291(5) Uani 1 1 d . . . . .
C3 C 0.5032(3) 0.2765(2) 0.6354(2) 0.0298(5) Uani 1 1 d . . . . .
C4 C 0.4391(3) 0.2080(2) 0.5262(2) 0.0333(6) Uani 1 1 d . . . . .
H4 H 0.362851 0.137424 0.519853 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4859(3) 0.2423(2) 0.4289(2) 0.0340(6) Uani 1 1 d . . . . .
C6 C 0.5983(3) 0.3472(2) 0.4364(2) 0.0324(6) Uani 1 1 d . . . . .
C7 C 0.6597(3) 0.4130(2) 0.5446(2) 0.0316(5) Uani 1 1 d . . . . .
H7 H 0.734907 0.483913 0.550152 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6169(3) 0.3807(2) 0.6464(2) 0.0284(5) Uani 1 1 d . . . . .
C9 C 0.6880(3) 0.4511(2) 0.7625(2) 0.0297(5) Uani 1 1 d . . . . .
C10 C 0.6435(3) 0.4144(2) 0.8567(2) 0.0317(5) Uani 1 1 d . . . . .
H10 H 0.693845 0.460817 0.929989 0.038 Uiso 1 1 calc R U . . .
C11 C 0.5211(3) 0.3063(2) 0.8576(2) 0.0301(5) Uani 1 1 d . . . . .
O12 O 0.4312(3) 0.18194(17) 0.31897(18) 0.0459(5) Uani 1 1 d . . . . .
C13 C 0.3170(5) 0.0754(3) 0.3061(3) 0.0679(11) Uani 1 1 d . . . . .
H13A H 0.288393 0.039507 0.224753 0.102 Uiso 1 1 calc R U . . .
H13B H 0.217103 0.091673 0.321355 0.102 Uiso 1 1 calc R U . . .
H13C H 0.366931 0.021669 0.363379 0.102 Uiso 1 1 calc R U . . .
C14 C 0.6481(4) 0.3835(2) 0.3291(2) 0.0394(6) Uani 1 1 d . . . . .
H14A H 0.729946 0.455978 0.350459 0.059 Uiso 1 1 calc R U . . .
H14B H 0.551040 0.396614 0.265188 0.059 Uiso 1 1 calc R U . . .
H14C H 0.695931 0.321698 0.301684 0.059 Uiso 1 1 calc R U . . .
C15 C 0.8156(3) 0.5608(2) 0.7716(2) 0.0338(6) Uani 1 1 d . . . . .
H15 H 0.780251 0.599787 0.695394 0.041 Uiso 1 1 calc R U . . .
C16 C 0.8313(4) 0.6498(2) 0.8740(3) 0.0456(7) Uani 1 1 d . . . . .
H16A H 0.905153 0.721798 0.868679 0.068 Uiso 1 1 calc R U . . .
H16B H 0.876555 0.617069 0.950503 0.068 Uiso 1 1 calc R U . . .
H16C H 0.722384 0.667526 0.868183 0.068 Uiso 1 1 calc R U . . .
C17 C 0.9844(4) 0.5295(3) 0.7829(3) 0.0487(7) Uani 1 1 d . . . . .
H17A H 1.063473 0.600963 0.784782 0.073 Uiso 1 1 calc R U . . .
H17B H 0.975456 0.476677 0.714374 0.073 Uiso 1 1 calc R U . . .
H17C H 1.022508 0.490656 0.856776 0.073 Uiso 1 1 calc R U . . .
C18 C 0.3796(3) 0.3443(2) 0.8941(3) 0.0392(6) Uani 1 1 d . . . . .
H18A H 0.423458 0.385215 0.973821 0.059 Uiso 1 1 calc R U . . .
H18B H 0.298206 0.275079 0.895023 0.059 Uiso 1 1 calc R U . . .
H18C H 0.326857 0.396802 0.836547 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6102(3) 0.2227(2) 0.9433(2) 0.0292(5) Uani 1 1 d . . . . .
C20 C 0.7476(3) 0.1874(2) 0.9238(2) 0.0328(6) Uani 1 1 d . . . . .
H20 H 0.787928 0.220403 0.862795 0.039 Uiso 1 1 calc R U . . .
C21 C 0.8262(3) 0.1055(2) 0.9913(2) 0.0344(6) Uani 1 1 d . . . . .
H21 H 0.918721 0.082130 0.975988 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7692(3) 0.0576(2) 1.0811(2) 0.0350(6) Uani 1 1 d . . . . .
C23 C 0.6372(3) 0.0955(2) 1.1055(2) 0.0371(6) Uani 1 1 d . . . . .
H23 H 0.601291 0.065842 1.169607 0.044 Uiso 1 1 calc R U . . .
C24 C 0.5580(3) 0.1763(2) 1.0362(2) 0.0345(6) Uani 1 1 d . . . . .
H24 H 0.466601 0.200433 1.052427 0.041 Uiso 1 1 calc R U . . .
O25 O 0.8469(3) -0.02625(19) 1.1424(2) 0.0464(5) Uani 1 1 d . . . . .
H25 H 0.790(5) -0.059(3) 1.181(3) 0.070 Uiso 1 1 d . U . . .
C26 C -0.0063(6) 0.1835(4) 0.5495(4) 0.0401(9) Uani 0.849(7) 1 d D U P A 1
H26 H 0.093170 0.145463 0.574857 0.048 Uiso 0.849(7) 1 calc R U P A 1
Cl27 Cl 0.0517(5) 0.3218(3) 0.5032(4) 0.0663(9) Uani 0.849(7) 1 d D U P A 1
Cl28 Cl -0.1568(2) 0.09447(15) 0.43283(16) 0.0629(6) Uani 0.849(7) 1 d D U P A
1
Cl29 Cl -0.0787(3) 0.19711(16) 0.67188(17) 0.0529(4) Uani 0.849(7) 1 d D U P A
1
C36 C 0.013(4) 0.188(2) 0.5389(19) 0.053(4) Uani 0.151(7) 1 d D U P A 2
H36 H 0.110384 0.149775 0.574954 0.064 Uiso 0.151(7) 1 calc R U P A 2
Cl37 Cl 0.081(2) 0.3356(16) 0.5289(19) 0.053(3) Uani 0.151(7) 1 d D U P A 2
Cl38 Cl -0.0877(19) 0.1255(8) 0.3935(11) 0.082(4) Uani 0.151(7) 1 d D U P A 2
Cl39 Cl -0.1171(17) 0.1681(13) 0.6273(16) 0.083(3) Uani 0.151(7) 1 d D U P A 2


_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 C2 1.229(3) . ?
C2 C3 1.463(3) . ?
C2 C11 1.535(4) . ?
C3 C8 1.405(3) . ?
C3 C4 1.406(4) . ?
C4 C5 1.372(4) . ?
C4 H4 0.9500 . ?
C5 O12 1.370(3) . ?
C5 C6 1.410(3) . ?
C6 C7 1.383(4) . ?
C6 C14 1.500(4) . ?
C7 C8 1.397(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.484(3) . ?
C9 C10 1.336(4) . ?
C9 C15 1.521(3) . ?
C10 C11 1.506(3) . ?
C10 H10 0.9500 . ?
C11 C18 1.537(3) . ?
C11 C19 1.540(3) . ?
O12 C13 1.425(4) . ?
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 C17 1.530(4) . ?
C15 C16 1.532(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.389(3) . ?
C19 C20 1.398(3) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 O25 1.368(3) . ?
C22 C23 1.391(4) . ?
C23 C24 1.387(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O25 H25 0.82(4) . ?
C26 Cl27 1.749(4) . ?
C26 Cl29 1.750(4) . ?
C26 Cl28 1.753(4) . ?
C26 H26 1.0000 . ?
C36 Cl39 1.740(18) . ?
C36 Cl37 1.741(18) . ?
C36 Cl38 1.747(18) . ?
C36 H36 1.0000 . ?

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
O1 C2 C3 121.4(2) . . ?
O1 C2 C11 119.1(2) . . ?
C3 C2 C11 119.4(2) . . ?
C8 C3 C4 120.4(2) . . ?
C8 C3 C2 121.4(2) . . ?
C4 C3 C2 118.3(2) . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
O12 C5 C4 125.1(2) . . ?
O12 C5 C6 114.4(2) . . ?
C4 C5 C6 120.6(2) . . ?
C7 C6 C5 117.8(2) . . ?
C7 C6 C14 122.2(2) . . ?
C5 C6 C14 119.9(2) . . ?
C6 C7 C8 123.5(2) . . ?
C6 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C3 117.2(2) . . ?
C7 C8 C9 122.5(2) . . ?
C3 C8 C9 120.3(2) . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 C15 121.9(2) . . ?
C8 C9 C15 118.5(2) . . ?
C9 C10 C11 126.1(2) . . ?
C9 C10 H10 117.0 . . ?
C11 C10 H10 117.0 . . ?
C10 C11 C2 113.2(2) . . ?
C10 C11 C18 108.2(2) . . ?
C2 C11 C18 107.7(2) . . ?
C10 C11 C19 108.9(2) . . ?
C2 C11 C19 106.13(19) . . ?
C18 C11 C19 112.8(2) . . ?
C5 O12 C13 116.8(2) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 C17 110.8(2) . . ?
C9 C15 C16 113.8(2) . . ?
C17 C15 C16 109.7(2) . . ?
C9 C15 H15 107.4 . . ?
C17 C15 H15 107.4 . . ?
C16 C15 H15 107.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 117.9(2) . . ?
C24 C19 C11 123.8(2) . . ?
C20 C19 C11 118.2(2) . . ?
C21 C20 C19 121.5(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 119.7(2) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
O25 C22 C21 117.6(3) . . ?
O25 C22 C23 122.8(2) . . ?
C21 C22 C23 119.6(3) . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 121.1(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C22 O25 H25 109(3) . . ?
Cl27 C26 Cl29 110.2(3) . . ?
Cl27 C26 Cl28 111.2(3) . . ?
Cl29 C26 Cl28 110.2(2) . . ?
Cl27 C26 H26 108.4 . . ?
Cl29 C26 H26 108.4 . . ?
Cl28 C26 H26 108.4 . . ?
Cl39 C36 Cl37 111.2(17) . . ?
Cl39 C36 Cl38 111.4(14) . . ?
Cl37 C36 Cl38 107.3(15) . . ?
Cl39 C36 H36 109.0 . . ?
Cl37 C36 H36 109.0 . . ?
Cl38 C36 H36 109.0 . . ?

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
O1 C2 C3 C8 174.5(2) . . . . ?
C11 C2 C3 C8 -4.7(4) . . . . ?
O1 C2 C3 C4 -4.4(4) . . . . ?
C11 C2 C3 C4 176.5(2) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C5 178.5(2) . . . . ?
C3 C4 C5 O12 179.8(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
O12 C5 C6 C7 -179.8(2) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
O12 C5 C6 C14 -0.1(4) . . . . ?
C4 C5 C6 C14 -180.0(3) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C14 C6 C7 C8 -179.3(3) . . . . ?
C6 C7 C8 C3 -1.1(4) . . . . ?
C6 C7 C8 C9 178.2(2) . . . . ?
C4 C3 C8 C7 1.1(4) . . . . ?
C2 C3 C8 C7 -177.7(2) . . . . ?
C4 C3 C8 C9 -178.3(2) . . . . ?
C2 C3 C8 C9 2.9(4) . . . . ?
C7 C8 C9 C10 -179.1(3) . . . . ?
C3 C8 C9 C10 0.3(4) . . . . ?
C7 C8 C9 C15 -1.7(4) . . . . ?
C3 C8 C9 C15 177.7(2) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
C15 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C2 -0.2(4) . . . . ?
C9 C10 C11 C18 -119.5(3) . . . . ?
C9 C10 C11 C19 117.6(3) . . . . ?
O1 C2 C11 C10 -175.9(2) . . . . ?
C3 C2 C11 C10 3.3(3) . . . . ?
O1 C2 C11 C18 -56.4(3) . . . . ?
C3 C2 C11 C18 122.8(2) . . . . ?
O1 C2 C11 C19 64.7(3) . . . . ?
C3 C2 C11 C19 -116.1(2) . . . . ?
C4 C5 O12 C13 0.0(4) . . . . ?
C6 C5 O12 C13 -179.8(3) . . . . ?
C10 C9 C15 C17 99.2(3) . . . . ?
C8 C9 C15 C17 -78.1(3) . . . . ?
C10 C9 C15 C16 -25.0(4) . . . . ?
C8 C9 C15 C16 157.7(2) . . . . ?
C10 C11 C19 C24 126.6(3) . . . . ?
C2 C11 C19 C24 -111.2(3) . . . . ?
C18 C11 C19 C24 6.5(3) . . . . ?
C10 C11 C19 C20 -56.2(3) . . . . ?
C2 C11 C19 C20 66.0(3) . . . . ?
C18 C11 C19 C20 -176.3(2) . . . . ?
C24 C19 C20 C21 2.4(4) . . . . ?
C11 C19 C20 C21 -174.9(2) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 O25 177.6(2) . . . . ?
C20 C21 C22 C23 -2.2(4) . . . . ?
O25 C22 C23 C24 -176.6(2) . . . . ?
C21 C22 C23 C24 3.2(4) . . . . ?
C22 C23 C24 C19 -1.3(4) . . . . ?
C20 C19 C24 C23 -1.5(4) . . . . ?
C11 C19 C24 C23 175.7(2) . . . . ?

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
O25 H25 O1 0.82(4) 2.01(4) 2.825(3) 175(4) 2_657 yes

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060

























