# Electronic Supplementary Material (ESI) for Chemical Science.
# 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 
# this file and to allow appropriate attribution of the data. 
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data_220815_wq_ngd_hjw_c_158_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2202510'
loop_
_audit_author_name
_audit_author_address
hjww
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-08-21 deposited with the CCDC.	2023-12-07 downloaded from the CCDC.
;
_audit_creation_date             2022-08-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O3'
_chemical_formula_sum            'C20 H20 O3'
_chemical_formula_weight         308.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.9435(14)
_cell_length_b                   5.7917(2)
_cell_length_c                   17.1106(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.733(2)
_cell_angle_gamma                90
_cell_volume                     3281.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6211
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.09
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0916 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.9397.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16677
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.087
_diffrn_reflns_theta_min         2.461
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3407
_reflns_number_total             4363
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.020
_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)+(0.0366P)²+2.4475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1099
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C18(H18), C15(H15), C16(H16), C1(H1), C17(H17), C3(H3),
 C5(H5), C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.40461(3) -0.07822(16) 0.11253(5) 0.0329(2) Uani 1 1 d . . . . .
O1 O 0.31562(3) 0.73858(17) 0.18570(6) 0.0389(2) Uani 1 1 d . . . . .
O3 O 0.46645(3) 0.04725(19) 0.16942(7) 0.0442(3) Uani 1 1 d . . . . .
C13 C 0.42879(3) 0.4923(2) 0.32779(7) 0.0253(2) Uani 1 1 d . . . . .
C12 C 0.43742(3) 0.3234(2) 0.26941(7) 0.0260(2) Uani 1 1 d . . . . .
H12 H 0.464810 0.277154 0.276022 0.031 Uiso 1 1 calc R . . . .
C11 C 0.41108(3) 0.2272(2) 0.20800(7) 0.0245(2) Uani 1 1 d . . . . .
C7 C 0.29133(3) 0.6288(2) 0.13682(7) 0.0267(2) Uani 1 1 d . . . . .
C10 C 0.36595(3) 0.2611(2) 0.18831(7) 0.0254(2) Uani 1 1 d . . . . .
H10A H 0.358194 0.346783 0.232674 0.030 Uiso 1 1 calc R . . . .
H10B H 0.352705 0.107956 0.184637 0.030 Uiso 1 1 calc R . . . .
C14 C 0.40299(3) 0.6797(2) 0.30522(7) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.389803 0.699305 0.250593 0.033 Uiso 1 1 calc R . . . .
C19 C 0.42599(3) 0.0508(2) 0.15832(7) 0.0260(2) Uani 1 1 d . . . . .
C18 C 0.44798(4) 0.4687(2) 0.40847(8) 0.0311(3) Uani 1 1 d . . . . .
H18 H 0.466036 0.343620 0.424749 0.037 Uiso 1 1 calc R . . . .
C15 C 0.39644(4) 0.8373(2) 0.36188(8) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.378892 0.964642 0.345745 0.038 Uiso 1 1 calc R . . . .
C6 C 0.24762(3) 0.6953(2) 0.11919(7) 0.0272(3) Uani 1 1 d . . . . .
C9 C 0.35024(3) 0.3922(2) 0.10987(7) 0.0277(3) Uani 1 1 d . . . . .
H9A H 0.363752 0.544520 0.112987 0.033 Uiso 1 1 calc R . . . .
H9B H 0.357391 0.305138 0.065169 0.033 Uiso 1 1 calc R . . . .
C8 C 0.30455(3) 0.4283(2) 0.09210(8) 0.0280(3) Uani 1 1 d . . . . .
H8A H 0.294768 0.454248 0.033854 0.034 Uiso 1 1 calc R . . . .
H8B H 0.291645 0.285529 0.106164 0.034 Uiso 1 1 calc R . . . .
C16 C 0.41523(4) 0.8111(2) 0.44171(8) 0.0351(3) Uani 1 1 d . . . . .
H16 H 0.410536 0.919420 0.480347 0.042 Uiso 1 1 calc R . . . .
C1 C 0.21842(4) 0.5792(2) 0.06330(9) 0.0346(3) Uani 1 1 d . . . . .
H1 H 0.225859 0.449214 0.035896 0.041 Uiso 1 1 calc R . . . .
C17 C 0.44096(4) 0.6256(3) 0.46501(8) 0.0361(3) Uani 1 1 d . . . . .
H17 H 0.453799 0.606004 0.519836 0.043 Uiso 1 1 calc R . . . .
C3 C 0.16745(4) 0.8399(3) 0.08717(9) 0.0418(3) Uani 1 1 d . . . . .
H3 H 0.140088 0.889129 0.076203 0.050 Uiso 1 1 calc R . . . .
C5 C 0.23604(4) 0.8847(2) 0.15916(8) 0.0358(3) Uani 1 1 d . . . . .
H5 H 0.255665 0.965028 0.197757 0.043 Uiso 1 1 calc R . . . .
C2 C 0.17849(4) 0.6518(3) 0.04722(10) 0.0419(3) Uani 1 1 d . . . . .
H2 H 0.158725 0.572035 0.008716 0.050 Uiso 1 1 calc R . . . .
C4 C 0.19612(4) 0.9566(3) 0.14300(9) 0.0427(3) Uani 1 1 d . . . . .
H4 H 0.188478 1.086120 0.170344 0.051 Uiso 1 1 calc R . . . .
C20 C 0.48299(4) -0.1378(3) 0.13035(11) 0.0519(4) Uani 1 1 d . . . . .
H20A H 0.473742 -0.122426 0.072154 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.473937 -0.286294 0.147544 0.078 Uiso 1 1 calc GR . . . .
H20C H 0.512557 -0.130583 0.144795 0.078 Uiso 1 1 calc GR . . . .


_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
O2 C19 1.2032(15) . ?
O1 C7 1.2164(15) . ?
O3 C19 1.3446(14) . ?
O3 C20 1.4410(17) . ?
C13 C12 1.4730(17) . ?
C13 C14 1.3947(17) . ?
C13 C18 1.3972(17) . ?
C12 C11 1.3413(17) . ?
C11 C10 1.5070(15) . ?
C11 C19 1.4875(16) . ?
C7 C6 1.4979(16) . ?
C7 C8 1.5123(17) . ?
C10 C9 1.5323(17) . ?
C14 C15 1.3847(17) . ?
C18 C17 1.3857(19) . ?
C15 C16 1.3827(19) . ?
C6 C1 1.3895(18) . ?
C6 C5 1.3941(18) . ?
C9 C8 1.5276(16) . ?
C16 C17 1.387(2) . ?
C1 C2 1.3877(18) . ?
C3 C2 1.381(2) . ?
C3 C4 1.381(2) . ?
C5 C4 1.3861(19) . ?

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
C19 O3 C20 115.86(11) . . ?
C14 C13 C12 122.39(11) . . ?
C14 C13 C18 118.51(11) . . ?
C18 C13 C12 119.08(11) . . ?
C11 C12 C13 127.53(11) . . ?
C12 C11 C10 126.18(11) . . ?
C12 C11 C19 118.75(10) . . ?
C19 C11 C10 114.74(10) . . ?
O1 C7 C6 119.70(11) . . ?
O1 C7 C8 121.16(11) . . ?
C6 C7 C8 119.13(10) . . ?
C11 C10 C9 113.62(10) . . ?
C15 C14 C13 120.47(12) . . ?
O2 C19 O3 122.21(11) . . ?
O2 C19 C11 124.51(11) . . ?
O3 C19 C11 113.28(10) . . ?
C17 C18 C13 120.74(12) . . ?
C16 C15 C14 120.60(13) . . ?
C1 C6 C7 122.60(11) . . ?
C1 C6 C5 118.88(11) . . ?
C5 C6 C7 118.50(11) . . ?
C8 C9 C10 112.59(10) . . ?
C7 C8 C9 113.94(10) . . ?
C15 C16 C17 119.56(12) . . ?
C2 C1 C6 120.47(13) . . ?
C18 C17 C16 120.12(12) . . ?
C2 C3 C4 120.13(13) . . ?
C4 C5 C6 120.49(13) . . ?
C3 C2 C1 120.03(14) . . ?
C3 C4 C5 119.99(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
