# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_cxy1822
_database_code_depnum_ccdc_archive 'CCDC 2296186'
loop_
_audit_author_name
_audit_author_address
'Xiao ZHANG'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-10-06 downloaded from the CCDC.
;
_audit_creation_date             2021-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            cxy1822
_chemical_name_systematic        3ao
_chemical_formula_moiety         'C20 H22 O3'
_chemical_formula_sum            'C20 H22 O3'
_chemical_formula_weight         310.37
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.4702(3)
_cell_length_b                   9.9613(4)
_cell_length_c                   25.6312(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1651.97(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.61
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0648 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.9387.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19161
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.603
_diffrn_reflns_theta_min         3.449
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2959
_reflns_number_total             3041
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(6)
_refine_ls_extinction_coef       0.0086(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.034
_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)+(0.0343P)²+0.2813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C12(H12), C16(H16), C17(H17), C19(H19), C20(H20)
2.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_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
O1 O -0.77359(18) -0.50958(12) -0.47148(4) 0.0248(3) Uani 1 1 d . . . . .
O2 O -0.45371(18) -0.35968(11) -0.45550(4) 0.0226(3) Uani 1 1 d . . . . .
O3 O -0.82128(18) -0.32878(11) -0.09815(4) 0.0219(3) Uani 1 1 d . . . . .
C1 C -0.9477(3) -0.59364(19) -0.48215(7) 0.0309(4) Uani 1 1 d . . . . .
H1A H -1.067252 -0.561965 -0.462161 0.046 Uiso 1 1 calc R U . . .
H1B H -0.915499 -0.686227 -0.472093 0.046 Uiso 1 1 calc R U . . .
H1C H -0.979646 -0.590337 -0.519500 0.046 Uiso 1 1 calc R U . . .
C2 C -0.7077(2) -0.50331(16) -0.42092(5) 0.0184(3) Uani 1 1 d . . . . .
C3 C -0.5314(2) -0.42223(15) -0.41226(6) 0.0175(3) Uani 1 1 d . . . . .
C4 C -0.4530(2) -0.40830(14) -0.36257(6) 0.0172(3) Uani 1 1 d . . . . .
H4 H -0.334013 -0.354124 -0.357252 0.021 Uiso 1 1 calc R U . . .
C5 C -0.5452(2) -0.47258(14) -0.31940(5) 0.0157(3) Uani 1 1 d . . . . .
C6 C -0.4565(2) -0.45491(14) -0.26615(5) 0.0163(3) Uani 1 1 d . . . . .
C7 C -0.5761(2) -0.50805(15) -0.21987(5) 0.0164(3) Uani 1 1 d . . . . .
H7A H -0.483717 -0.510265 -0.189092 0.020 Uiso 1 1 calc R U . . .
H7B H -0.619751 -0.601374 -0.227294 0.020 Uiso 1 1 calc R U . . .
C8 C -0.7698(2) -0.42321(14) -0.20648(6) 0.0165(3) Uani 1 1 d . . . . .
H8 H -0.854550 -0.414078 -0.238912 0.020 Uiso 1 1 calc R U . . .
C9 C -0.9008(2) -0.49284(15) -0.16568(6) 0.0160(3) Uani 1 1 d . . . . .
C10 C -0.9215(2) -0.44217(15) -0.11511(6) 0.0176(3) Uani 1 1 d . . . . .
C11 C -1.0515(3) -0.50417(17) -0.07885(6) 0.0218(3) Uani 1 1 d . . . . .
H11 H -1.065021 -0.468181 -0.044693 0.026 Uiso 1 1 calc R U . . .
C12 C -1.1603(3) -0.61803(17) -0.09283(6) 0.0240(3) Uani 1 1 d . . . . .
H12 H -1.249368 -0.659908 -0.068268 0.029 Uiso 1 1 calc R U . . .
C13 C -0.2841(3) -0.26934(17) -0.44721(6) 0.0267(4) Uani 1 1 d . . . . .
H13A H -0.163844 -0.319851 -0.434778 0.040 Uiso 1 1 calc R U . . .
H13B H -0.323076 -0.202059 -0.421104 0.040 Uiso 1 1 calc R U . . .
H13C H -0.249628 -0.224392 -0.480089 0.040 Uiso 1 1 calc R U . . .
C14 C -0.7142(3) -0.28193(15) -0.18753(6) 0.0211(3) Uani 1 1 d . . . . .
H14A H -0.598495 -0.246138 -0.208630 0.025 Uiso 1 1 calc R U . . .
H14B H -0.834457 -0.221630 -0.192104 0.025 Uiso 1 1 calc R U . . .
C15 C -0.6523(3) -0.28530(16) -0.13046(6) 0.0226(3) Uani 1 1 d . . . . .
H15A H -0.533962 -0.347191 -0.125886 0.027 Uiso 1 1 calc R U . . .
H15B H -0.607684 -0.194566 -0.119431 0.027 Uiso 1 1 calc R U . . .
C16 C -1.0121(2) -0.60879(15) -0.17830(6) 0.0192(3) Uani 1 1 d . . . . .
H16 H -0.999453 -0.645361 -0.212381 0.023 Uiso 1 1 calc R U . . .
C17 C -1.1399(3) -0.67169(17) -0.14275(6) 0.0229(3) Uani 1 1 d . . . . .
H17 H -1.213088 -0.750684 -0.152231 0.028 Uiso 1 1 calc R U . . .
C18 C -0.2771(3) -0.39287(16) -0.25794(6) 0.0209(3) Uani 1 1 d . . . . .
H18A H -0.200862 -0.358033 -0.286572 0.025 Uiso 1 1 calc R U . . .
H18B H -0.225350 -0.383462 -0.223442 0.025 Uiso 1 1 calc R U . . .
C19 C -0.7185(2) -0.55111(14) -0.32875(6) 0.0180(3) Uani 1 1 d . . . . .
H19 H -0.783856 -0.595220 -0.300332 0.022 Uiso 1 1 calc R U . . .
C20 C -0.7993(3) -0.56687(15) -0.37907(6) 0.0198(3) Uani 1 1 d . . . . .
H20 H -0.917687 -0.621578 -0.384403 0.024 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.430(2) . ?
O1 C2 1.3655(17) . ?
O2 C3 1.3672(18) . ?
O2 C13 1.435(2) . ?
O3 C10 1.3731(19) . ?
O3 C15 1.4384(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.415(2) . ?
C2 C20 1.379(2) . ?
C3 C4 1.378(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.411(2) . ?
C5 C6 1.491(2) . ?
C5 C19 1.388(2) . ?
C6 C7 1.5118(19) . ?
C6 C18 1.332(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.550(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.514(2) . ?
C8 C14 1.532(2) . ?
C9 C10 1.397(2) . ?
C9 C16 1.399(2) . ?
C10 C11 1.397(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C12 C17 1.393(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.517(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C17 1.381(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.401(2) . ?
C20 H20 0.9500 . ?

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 O1 C1 117.00(12) . . ?
C3 O2 C13 116.55(12) . . ?
C10 O3 C15 115.12(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 115.24(13) . . ?
O1 C2 C20 125.66(14) . . ?
C20 C2 C3 119.09(13) . . ?
O2 C3 C2 115.43(13) . . ?
O2 C3 C4 124.60(14) . . ?
C4 C3 C2 119.95(13) . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.57(14) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 120.12(13) . . ?
C19 C5 C4 117.52(13) . . ?
C19 C5 C6 122.36(13) . . ?
C5 C6 C7 118.69(13) . . ?
C18 C6 C5 122.32(14) . . ?
C18 C6 C7 118.98(13) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C6 C7 C8 113.36(12) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8 108.0 . . ?
C9 C8 C7 110.84(11) . . ?
C9 C8 H8 108.0 . . ?
C9 C8 C14 109.47(12) . . ?
C14 C8 C7 112.41(13) . . ?
C14 C8 H8 108.0 . . ?
C10 C9 C8 121.93(13) . . ?
C10 C9 C16 117.60(13) . . ?
C16 C9 C8 120.44(13) . . ?
O3 C10 C9 123.06(13) . . ?
O3 C10 C11 115.93(13) . . ?
C11 C10 C9 121.00(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.79(14) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C17 120.32(14) . . ?
C17 C12 H12 119.8 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.6 . . ?
C8 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 C8 110.34(12) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
O3 C15 C14 111.18(13) . . ?
O3 C15 H15A 109.4 . . ?
O3 C15 H15B 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C9 C16 H16 119.0 . . ?
C17 C16 C9 122.03(14) . . ?
C17 C16 H16 119.0 . . ?
C12 C17 H17 120.4 . . ?
C16 C17 C12 119.26(15) . . ?
C16 C17 H17 120.4 . . ?
C6 C18 H18A 120.0 . . ?
C6 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C5 C19 H19 119.2 . . ?
C5 C19 C20 121.58(14) . . ?
C20 C19 H19 119.2 . . ?
C2 C20 C19 120.29(14) . . ?
C2 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?

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 O2 1.1(2) . . . . ?
O1 C2 C3 C4 179.58(13) . . . . ?
O1 C2 C20 C19 -179.12(15) . . . . ?
O2 C3 C4 C5 177.93(13) . . . . ?
O3 C10 C11 C12 179.27(14) . . . . ?
C1 O1 C2 C3 178.20(14) . . . . ?
C1 O1 C2 C20 -2.6(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C2 C20 C19 0.0(2) . . . . ?
C3 C4 C5 C6 -179.81(13) . . . . ?
C3 C4 C5 C19 0.1(2) . . . . ?
C4 C5 C6 C7 171.15(13) . . . . ?
C4 C5 C6 C18 -8.1(2) . . . . ?
C4 C5 C19 C20 0.2(2) . . . . ?
C5 C6 C7 C8 -73.08(17) . . . . ?
C5 C19 C20 C2 -0.3(2) . . . . ?
C6 C5 C19 C20 -179.81(14) . . . . ?
C6 C7 C8 C9 171.07(12) . . . . ?
C6 C7 C8 C14 -66.07(16) . . . . ?
C7 C8 C9 C10 111.58(15) . . . . ?
C7 C8 C9 C16 -70.79(17) . . . . ?
C7 C8 C14 C15 -80.40(16) . . . . ?
C8 C9 C10 O3 -1.9(2) . . . . ?
C8 C9 C10 C11 176.70(14) . . . . ?
C8 C9 C16 C17 -177.23(14) . . . . ?
C8 C14 C15 O3 -62.91(17) . . . . ?
C9 C8 C14 C15 43.23(17) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C9 C16 C17 C12 0.4(2) . . . . ?
C10 O3 C15 C14 47.98(18) . . . . ?
C10 C9 C16 C17 0.5(2) . . . . ?
C10 C11 C12 C17 0.4(2) . . . . ?
C11 C12 C17 C16 -0.9(2) . . . . ?
C13 O2 C3 C2 175.68(14) . . . . ?
C13 O2 C3 C4 -2.8(2) . . . . ?
C14 C8 C9 C10 -12.97(19) . . . . ?
C14 C8 C9 C16 164.66(13) . . . . ?
C15 O3 C10 C9 -15.9(2) . . . . ?
C15 O3 C10 C11 165.39(14) . . . . ?
C16 C9 C10 O3 -179.62(14) . . . . ?
C16 C9 C10 C11 -1.0(2) . . . . ?
C18 C6 C7 C8 106.24(16) . . . . ?
C19 C5 C6 C7 -8.8(2) . . . . ?
C19 C5 C6 C18 171.91(14) . . . . ?
C20 C2 C3 O2 -178.16(13) . . . . ?
C20 C2 C3 C4 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
