# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cu_d8v19418_0m
_database_code_depnum_ccdc_archive 'CCDC 1939837'
loop_
_audit_author_name
_audit_author_address
'Yuan Yuan'
;Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University
China
;
_audit_update_record             
;
2019-07-11 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 O'
_chemical_formula_weight         312.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.8749(4)
_cell_length_b                   6.1545(2)
_cell_length_c                   12.1392(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.3690(10)
_cell_angle_gamma                90
_cell_volume                     855.46(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9774
_cell_measurement_theta_min      7.553
_cell_measurement_theta_max      140.282

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.558
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_T_max  0.7513
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11285
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.776
_diffrn_reflns_theta_max         67.384
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3022
_reflns_number_gt                2937
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.971

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0733P)²+0.0304P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.069(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.06(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3022
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.23583(15) 0.1839(3) 0.07775(15) 0.0624(5) Uani 1 1 d . . . . .
C1 C 0.28711(18) 0.3264(3) 0.13989(17) 0.0459(5) Uani 1 1 d . . . . .
C2 C 0.21844(17) 0.4797(3) 0.19948(17) 0.0442(5) Uani 1 1 d . . . . .
C3 C 0.21071(17) 0.6919(3) 0.13343(18) 0.0461(5) Uani 1 1 d . . . . .
H3 H 0.2387 0.8204 0.1751 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1675(2) 0.7082(4) 0.0218(2) 0.0535(5) Uani 1 1 d . . . . .
C5 C 0.09404(18) 0.3798(4) 0.18408(18) 0.0488(5) Uani 1 1 d . . . . .
H5A H 0.0544 0.3720 0.1014 0.059 Uiso 1 1 calc R U . . .
H5B H 0.1027 0.2294 0.2140 0.059 Uiso 1 1 calc R U . . .
C6 C 0.01731(17) 0.5049(4) 0.24299(18) 0.0494(5) Uani 1 1 d . . . . .
C7 C -0.03776(19) 0.6962(5) 0.1982(2) 0.0581(6) Uani 1 1 d . . . . .
H7 H -0.0308 0.7473 0.1265 0.070 Uiso 1 1 calc R U . . .
C8 C -0.1031(2) 0.8144(5) 0.2570(2) 0.0671(7) Uani 1 1 d . . . . .
H8 H -0.1387 0.9473 0.2264 0.080 Uiso 1 1 calc R U . . .
C9 C -0.1163(2) 0.7385(5) 0.3599(2) 0.0672(7) Uani 1 1 d . . . . .
H9 H -0.1607 0.8194 0.4003 0.081 Uiso 1 1 calc R U . . .
C10 C -0.0655(2) 0.5469(6) 0.4035(2) 0.0671(7) Uani 1 1 d . . . . .
H10 H -0.0762 0.4924 0.4732 0.081 Uiso 1 1 calc R U . . .
C11 C 0.0020(2) 0.4311(5) 0.3456(2) 0.0601(6) Uani 1 1 d . . . . .
H11 H 0.0381 0.2993 0.3772 0.072 Uiso 1 1 calc R U . . .
C12 C 0.27713(17) 0.5034(3) 0.32766(17) 0.0442(5) Uani 1 1 d . . . . .
C13 C 0.26484(19) 0.6903(4) 0.3871(2) 0.0521(5) Uani 1 1 d . . . . .
H13 H 0.2224 0.8103 0.3474 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3141(2) 0.7038(5) 0.5045(2) 0.0595(6) Uani 1 1 d . . . . .
H14 H 0.3055 0.8330 0.5443 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3758(2) 0.5296(5) 0.56374(19) 0.0600(6) Uani 1 1 d . . . . .
H15 H 0.4100 0.5394 0.6437 0.072 Uiso 1 1 calc R U . . .
C16 C 0.3869(2) 0.3423(5) 0.50548(19) 0.0585(6) Uani 1 1 d . . . . .
H16 H 0.4287 0.2221 0.5456 0.070 Uiso 1 1 calc R U . . .
C17 C 0.33762(19) 0.3279(4) 0.38862(19) 0.0512(5) Uani 1 1 d . . . . .
H17 H 0.3451 0.1970 0.3496 0.061 Uiso 1 1 calc R U . . .
C18 C 0.41562(19) 0.3574(4) 0.15331(17) 0.0460(5) Uani 1 1 d . . . . .
C19 C 0.47766(18) 0.5401(4) 0.20332(18) 0.0516(5) Uani 1 1 d . . . . .
H19 H 0.4387 0.6529 0.2319 0.062 Uiso 1 1 calc R U . . .
C20 C 0.5964(2) 0.5584(5) 0.2117(2) 0.0592(6) Uani 1 1 d . . . . .
H20 H 0.6382 0.6838 0.2455 0.071 Uiso 1 1 calc R U . . .
C21 C 0.6537(2) 0.3934(5) 0.1706(2) 0.0640(7) Uani 1 1 d . . . . .
H21 H 0.7350 0.4051 0.1768 0.077 Uiso 1 1 calc R U . . .
C22 C 0.5924(2) 0.2117(5) 0.1206(2) 0.0643(7) Uani 1 1 d . . . . .
H22 H 0.6317 0.0988 0.0923 0.077 Uiso 1 1 calc R U . . .
C23 C 0.4740(2) 0.1938(4) 0.11160(18) 0.0552(6) Uani 1 1 d . . . . .
H23 H 0.4324 0.0690 0.0767 0.066 Uiso 1 1 calc R U . . .
H4A H 0.172(2) 0.849(5) -0.019(2) 0.055(7) Uiso 1 1 d . . . . .
H4B H 0.137(3) 0.582(6) -0.025(3) 0.072(9) Uiso 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 C1 1.211(3) . ?
C1 C18 1.503(3) . ?
C1 C2 1.546(3) . ?
C2 C3 1.522(3) . ?
C2 C12 1.534(3) . ?
C2 C5 1.565(3) . ?
C3 C4 1.320(3) . ?
C3 H3 0.9500 . ?
C4 H4A 1.00(3) . ?
C4 H4B 0.98(3) . ?
C5 C6 1.510(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.382(3) . ?
C6 C7 1.386(4) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.392(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9500 . ?
C23 H23 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
O1 C1 C18 119.23(19) . . ?
O1 C1 C2 119.54(19) . . ?
C18 C1 C2 121.17(17) . . ?
C3 C2 C12 113.60(16) . . ?
C3 C2 C1 104.05(16) . . ?
C12 C2 C1 112.24(16) . . ?
C3 C2 C5 110.54(16) . . ?
C12 C2 C5 108.62(16) . . ?
C1 C2 C5 107.60(16) . . ?
C4 C3 C2 124.0(2) . . ?
C4 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
C3 C4 H4A 120.7(16) . . ?
C3 C4 H4B 121.3(19) . . ?
H4A C4 H4B 118(2) . . ?
C6 C5 C2 114.33(17) . . ?
C6 C5 H5A 108.7 . . ?
C2 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C2 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C11 C6 C7 118.1(2) . . ?
C11 C6 C5 119.9(2) . . ?
C7 C6 C5 121.9(2) . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 121.1(3) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C17 118.48(19) . . ?
C13 C12 C2 121.65(18) . . ?
C17 C12 C2 119.71(18) . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C23 C18 C19 119.1(2) . . ?
C23 C18 C1 117.23(19) . . ?
C19 C18 C1 123.69(19) . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?

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 C1 C2 C3 -105.3(2) . . . . ?
C18 C1 C2 C3 71.7(2) . . . . ?
O1 C1 C2 C12 131.4(2) . . . . ?
C18 C1 C2 C12 -51.5(2) . . . . ?
O1 C1 C2 C5 12.0(3) . . . . ?
C18 C1 C2 C5 -170.93(17) . . . . ?
C12 C2 C3 C4 177.5(2) . . . . ?
C1 C2 C3 C4 55.1(3) . . . . ?
C5 C2 C3 C4 -60.1(3) . . . . ?
C3 C2 C5 C6 -70.0(2) . . . . ?
C12 C2 C5 C6 55.3(2) . . . . ?
C1 C2 C5 C6 177.03(17) . . . . ?
C2 C5 C6 C11 -101.8(2) . . . . ?
C2 C5 C6 C7 77.1(3) . . . . ?
C11 C6 C7 C8 2.2(3) . . . . ?
C5 C6 C7 C8 -176.7(2) . . . . ?
C6 C7 C8 C9 -1.7(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C7 C6 C11 C10 -0.9(4) . . . . ?
C5 C6 C11 C10 178.1(2) . . . . ?
C9 C10 C11 C6 -1.1(4) . . . . ?
C3 C2 C12 C13 33.8(3) . . . . ?
C1 C2 C12 C13 151.5(2) . . . . ?
C5 C2 C12 C13 -89.6(2) . . . . ?
C3 C2 C12 C17 -150.9(2) . . . . ?
C1 C2 C12 C17 -33.2(3) . . . . ?
C5 C2 C12 C17 85.7(2) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
C2 C12 C13 C14 176.8(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C12 0.8(3) . . . . ?
C13 C12 C17 C16 -1.7(3) . . . . ?
C2 C12 C17 C16 -177.12(19) . . . . ?
O1 C1 C18 C23 -12.5(3) . . . . ?
C2 C1 C18 C23 170.38(19) . . . . ?
O1 C1 C18 C19 166.7(2) . . . . ?
C2 C1 C18 C19 -10.4(3) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
C1 C18 C19 C20 -179.3(2) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C18 -0.4(4) . . . . ?
C19 C18 C23 C22 0.5(3) . . . . ?
C1 C18 C23 C22 179.8(2) . . . . ?

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

