# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_cxy3205_0m
_audit_block_doi                 10.5517/ccdc.csd.cc27sstn
_database_code_depnum_ccdc_archive 'CCDC 2079412'
loop_
_audit_author_name
_audit_author_address
'Gen-Qiang Chen'
;Southern university of science and technology
China
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_audit_creation_date             2021-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O'
_chemical_formula_sum            'C20 H16 O'
_chemical_formula_weight         272.33
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9234(7)
_cell_length_b                   5.6665(4)
_cell_length_c                   14.4134(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.079(3)
_cell_angle_gamma                90
_cell_volume                     700.30(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0869 before and 0.0534 after correction. The Ratio of minimum to maximum transmission is 0.8675. 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    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13047
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.180
_diffrn_reflns_theta_min         3.191
_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 D8 VENTURE'
_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_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2523
_reflns_number_total             2544
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1106 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_extinction_coef       0.0074(13)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.1146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.39418(14) 0.7166(2) 0.75575(9) 0.0310(3) Uani 1 1 d . . . . .
C1 C 0.8005(2) 0.5746(4) 0.44494(13) 0.0348(4) Uani 1 1 d . . . . .
H1A H 0.896073 0.480603 0.466100 0.052 Uiso 1 1 calc GR . . . .
H1B H 0.824829 0.728228 0.421413 0.052 Uiso 1 1 calc GR . . . .
H1C H 0.724769 0.491591 0.392859 0.052 Uiso 1 1 calc GR . . . .
C2 C 0.73241(18) 0.6108(3) 0.52874(11) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.76639(18) 0.8116(3) 0.58596(12) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.830305 0.931200 0.570718 0.028 Uiso 1 1 calc R . . . .
C4 C 0.70799(18) 0.8398(3) 0.66540(11) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.731927 0.978644 0.703581 0.026 Uiso 1 1 calc R . . . .
C5 C 0.61500(17) 0.6665(3) 0.68926(10) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.56146(18) 0.6952(3) 0.77979(11) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.605490 0.848107 0.809960 0.027 Uiso 1 1 calc R . . . .
C7 C 0.30294(19) 0.5345(3) 0.77121(11) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.36269(19) 0.3403(3) 0.82927(11) 0.0212(4) Uani 1 1 d . . . . .
C9 C 0.2575(2) 0.1686(3) 0.84158(12) 0.0259(4) Uani 1 1 d . . . . .
H9 H 0.295617 0.033406 0.879841 0.031 Uiso 1 1 calc R . . . .
C10 C 0.0987(2) 0.1916(4) 0.79905(13) 0.0296(4) Uani 1 1 d . . . . .
H10 H 0.029065 0.072445 0.807990 0.035 Uiso 1 1 calc R . . . .
C11 C 0.62688(19) 0.5039(3) 0.85319(11) 0.0218(3) Uani 1 1 d . . . . .
C12 C 0.78700(19) 0.5016(3) 0.89651(12) 0.0261(4) Uani 1 1 d . . . . .
H12 H 0.851099 0.618207 0.879434 0.031 Uiso 1 1 calc R . . . .
C13 C 0.85386(19) 0.3316(4) 0.96409(12) 0.0279(4) Uani 1 1 d . . . . .
H13 H 0.963357 0.330882 0.992937 0.034 Uiso 1 1 calc R . . . .
C14 C 0.76040(19) 0.1621(3) 0.98958(11) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.805579 0.046317 1.036693 0.030 Uiso 1 1 calc R . . . .
C15 C 0.60099(19) 0.1618(3) 0.94624(11) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.537670 0.045014 0.963997 0.026 Uiso 1 1 calc R . . . .
C16 C 0.53179(18) 0.3310(3) 0.87666(11) 0.0199(3) Uani 1 1 d . . . . .
C17 C 0.63561(18) 0.4399(3) 0.55177(11) 0.0226(3) Uani 1 1 d . . . . .
H17 H 0.608480 0.303653 0.512239 0.027 Uiso 1 1 calc R . . . .
C18 C 0.57860(17) 0.4659(3) 0.63135(11) 0.0214(3) Uani 1 1 d . . . . .
H18 H 0.514406 0.346621 0.646515 0.026 Uiso 1 1 calc R . . . .
C19 C 0.14338(19) 0.5594(3) 0.72905(12) 0.0271(4) Uani 1 1 d . . . . .
H19 H 0.104391 0.693673 0.690411 0.032 Uiso 1 1 calc R . . . .
C20 C 0.0416(2) 0.3880(4) 0.74362(12) 0.0290(4) Uani 1 1 d . . . . .
H20 H -0.067436 0.405321 0.715509 0.035 Uiso 1 1 calc R . . . .


_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 C6 1.4410(19) . ?
O1 C7 1.371(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.509(2) . ?
C2 C3 1.389(2) . ?
C2 C17 1.398(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(2) . ?
C5 C6 1.517(2) . ?
C5 C18 1.394(2) . ?
C6 H6 1.0000 . ?
C6 C11 1.514(2) . ?
C7 C8 1.396(2) . ?
C7 C19 1.392(2) . ?
C8 C9 1.397(2) . ?
C8 C16 1.475(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C10 C20 1.382(3) . ?
C11 C12 1.392(2) . ?
C11 C16 1.398(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.401(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
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
C7 O1 C6 121.32(13) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.11(16) . . ?
C3 C2 C17 118.32(14) . . ?
C17 C2 C1 120.56(16) . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.84(15) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.51(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.28(14) . . ?
C4 C5 C18 118.96(14) . . ?
C18 C5 C6 121.71(14) . . ?
O1 C6 C5 110.74(12) . . ?
O1 C6 H6 106.7 . . ?
O1 C6 C11 113.68(13) . . ?
C5 C6 H6 106.7 . . ?
C11 C6 C5 111.84(13) . . ?
C11 C6 H6 106.7 . . ?
O1 C7 C8 123.06(14) . . ?
O1 C7 C19 115.75(15) . . ?
C19 C7 C8 121.11(15) . . ?
C7 C8 C9 117.82(15) . . ?
C7 C8 C16 118.55(14) . . ?
C9 C8 C16 123.60(15) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.27(16) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.0 . . ?
C20 C10 C9 119.95(17) . . ?
C20 C10 H10 120.0 . . ?
C12 C11 C6 118.00(15) . . ?
C12 C11 C16 120.09(15) . . ?
C16 C11 C6 121.91(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.79(16) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.70(15) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.94(15) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.02(15) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C8 118.33(14) . . ?
C11 C16 C15 118.44(14) . . ?
C15 C16 C8 123.19(15) . . ?
C2 C17 H17 119.5 . . ?
C18 C17 C2 121.03(15) . . ?
C18 C17 H17 119.5 . . ?
C5 C18 H18 119.8 . . ?
C17 C18 C5 120.31(15) . . ?
C17 C18 H18 119.8 . . ?
C7 C19 H19 120.1 . . ?
C20 C19 C7 119.79(16) . . ?
C20 C19 H19 120.1 . . ?
C10 C20 C19 120.03(16) . . ?
C10 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?

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 C6 C11 C12 -166.54(14) . . . . ?
O1 C6 C11 C16 14.5(2) . . . . ?
O1 C7 C8 C9 178.37(15) . . . . ?
O1 C7 C8 C16 0.3(2) . . . . ?
O1 C7 C19 C20 -177.74(15) . . . . ?
C1 C2 C3 C4 -177.54(15) . . . . ?
C1 C2 C17 C18 176.84(15) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2 C17 C18 C5 1.1(2) . . . . ?
C3 C2 C17 C18 -1.9(2) . . . . ?
C3 C4 C5 C6 176.20(14) . . . . ?
C3 C4 C5 C18 -1.2(2) . . . . ?
C4 C5 C6 O1 116.01(15) . . . . ?
C4 C5 C6 C11 -116.09(16) . . . . ?
C4 C5 C18 C17 0.5(2) . . . . ?
C5 C6 C11 C12 67.14(19) . . . . ?
C5 C6 C11 C16 -111.85(16) . . . . ?
C6 O1 C7 C8 14.7(2) . . . . ?
C6 O1 C7 C19 -168.50(14) . . . . ?
C6 C5 C18 C17 -176.84(14) . . . . ?
C6 C11 C12 C13 180.00(15) . . . . ?
C6 C11 C16 C8 -1.2(2) . . . . ?
C6 C11 C16 C15 -179.21(14) . . . . ?
C7 O1 C6 C5 105.81(16) . . . . ?
C7 O1 C6 C11 -21.1(2) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C7 C8 C16 C11 -6.7(2) . . . . ?
C7 C8 C16 C15 171.18(14) . . . . ?
C7 C19 C20 C10 -0.7(3) . . . . ?
C8 C7 C19 C20 -0.8(2) . . . . ?
C8 C9 C10 C20 -0.3(3) . . . . ?
C9 C8 C16 C11 175.32(15) . . . . ?
C9 C8 C16 C15 -6.8(2) . . . . ?
C9 C10 C20 C19 1.2(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C11 C16 C8 179.85(14) . . . . ?
C12 C11 C16 C15 1.8(2) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C8 -179.22(14) . . . . ?
C14 C15 C16 C11 -1.3(2) . . . . ?
C16 C8 C9 C10 176.84(15) . . . . ?
C16 C11 C12 C13 -1.0(2) . . . . ?
C17 C2 C3 C4 1.2(2) . . . . ?
C18 C5 C6 O1 -66.64(19) . . . . ?
C18 C5 C6 C11 61.26(18) . . . . ?
C19 C7 C8 C9 1.7(2) . . . . ?
C19 C7 C8 C16 -176.35(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
