# Electronic Supplementary Material (ESI) for ChemComm.
# 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_481
_database_code_depnum_ccdc_archive 'CCDC 1890183'
loop_
_audit_author_name
_audit_author_address
'Weiqing Xie'
;Northwerst A
China
;
_audit_update_record             
;
2019-01-11 deposited with the CCDC.	2020-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 O2'
_chemical_formula_sum            'C24 H22 O2'
_chemical_formula_weight         342.42
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.87350(10)
_cell_length_b                   8.75670(10)
_cell_length_c                   31.8081(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1914.50(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4990
_cell_measurement_theta_min      5.24
_cell_measurement_theta_max      67.70

_exptl_crystal_description       platelike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5067
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9180
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         5.24
_diffrn_reflns_theta_max         68.10
_reflns_number_total             3341
_reflns_number_gt                3058
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.1244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0080(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_number_reflns         3341
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47092(15) 0.91982(14) 0.14945(4) 0.0556(3) Uani 1 1 d . . .
O2 O 0.42254(16) 0.67171(13) 0.12573(3) 0.0503(3) Uani 1 1 d . . .
C1 C 0.0011(3) 1.1014(2) 0.12810(7) 0.0755(6) Uani 1 1 d . . .
H1A H -0.1310 1.0791 0.1267 0.091 Uiso 1 1 calc R . .
C2 C 0.0627(4) 1.2483(2) 0.12010(8) 0.0895(8) Uani 1 1 d . . .
H2A H -0.0272 1.3232 0.1129 0.107 Uiso 1 1 calc R . .
C3 C 0.2572(4) 1.2840(2) 0.12271(8) 0.0826(7) Uani 1 1 d . . .
H3A H 0.2988 1.3834 0.1176 0.099 Uiso 1 1 calc R . .
C4 C 0.3898(3) 1.1728(2) 0.13281(7) 0.0674(5) Uani 1 1 d . . .
H4A H 0.5214 1.1967 0.1347 0.081 Uiso 1 1 calc R . .
C5 C 0.3272(3) 1.02477(18) 0.14013(6) 0.0527(4) Uani 1 1 d . . .
C6 C 0.1313(3) 0.98598(19) 0.13819(6) 0.0555(4) Uani 1 1 d . . .
C7 C 0.0716(2) 0.82507(19) 0.14847(6) 0.0548(4) Uani 1 1 d . . .
H7A H -0.0594 0.8256 0.1606 0.066 Uiso 1 1 calc R . .
C8 C 0.2150(2) 0.7644(2) 0.18065(5) 0.0530(4) Uani 1 1 d . . .
H8A H 0.2125 0.8277 0.2057 0.064 Uiso 1 1 calc R . .
H8B H 0.1802 0.6610 0.1886 0.064 Uiso 1 1 calc R . .
C9 C 0.4162(2) 0.76657(18) 0.16131(5) 0.0469(4) Uani 1 1 d . . .
C10 C 0.2821(2) 0.7077(2) 0.09374(5) 0.0525(4) Uani 1 1 d . . .
H10A H 0.2875 0.6300 0.0720 0.063 Uiso 1 1 calc R . .
H10B H 0.3168 0.8045 0.0809 0.063 Uiso 1 1 calc R . .
C11 C 0.0758(2) 0.71800(19) 0.11022(6) 0.0521(4) Uani 1 1 d . . .
H11A H 0.0384 0.6160 0.1200 0.063 Uiso 1 1 calc R . .
C12 C -0.0664(3) 0.7639(2) 0.07531(7) 0.0653(5) Uani 1 1 d . . .
H12A H -0.1883 0.7955 0.0880 0.078 Uiso 1 1 calc R . .
H12B H -0.0135 0.8508 0.0602 0.078 Uiso 1 1 calc R . .
C13 C -0.1060(3) 0.6370(2) 0.04448(6) 0.0552(4) Uani 1 1 d . . .
C14 C -0.2560(3) 0.5373(2) 0.05170(7) 0.0684(5) Uani 1 1 d . . .
H14A H -0.3319 0.5483 0.0757 0.082 Uiso 1 1 calc R . .
C15 C -0.2957(4) 0.4208(3) 0.02380(9) 0.0911(7) Uani 1 1 d . . .
H15A H -0.3990 0.3548 0.0290 0.109 Uiso 1 1 calc R . .
C16 C -0.1842(5) 0.4020(3) -0.01133(9) 0.0974(8) Uani 1 1 d . . .
H16A H -0.2117 0.3240 -0.0303 0.117 Uiso 1 1 calc R . .
C17 C -0.0333(4) 0.4978(3) -0.01834(8) 0.0923(8) Uani 1 1 d . . .
H17A H 0.0452 0.4837 -0.0418 0.111 Uiso 1 1 calc R . .
C18 C 0.0048(3) 0.6151(3) 0.00873(6) 0.0747(6) Uani 1 1 d . . .
H18A H 0.1072 0.6814 0.0030 0.090 Uiso 1 1 calc R . .
C19 C 0.5717(2) 0.7125(2) 0.19144(5) 0.0528(4) Uani 1 1 d . . .
C20 C 0.6595(3) 0.5721(2) 0.18728(7) 0.0650(5) Uani 1 1 d . . .
H20A H 0.6252 0.5090 0.1650 0.078 Uiso 1 1 calc R . .
C21 C 0.7980(3) 0.5236(3) 0.21580(8) 0.0849(7) Uani 1 1 d . . .
H21A H 0.8569 0.4288 0.2124 0.102 Uiso 1 1 calc R . .
C22 C 0.8488(3) 0.6142(4) 0.24900(8) 0.0932(9) Uani 1 1 d . . .
H22A H 0.9431 0.5820 0.2680 0.112 Uiso 1 1 calc R . .
C23 C 0.7589(3) 0.7534(4) 0.25403(7) 0.0913(8) Uani 1 1 d . . .
H23A H 0.7908 0.8146 0.2769 0.110 Uiso 1 1 calc R . .
C24 C 0.6215(3) 0.8032(3) 0.22532(6) 0.0732(6) Uani 1 1 d . . .
H24A H 0.5626 0.8979 0.2288 0.088 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 C5 1.381(2) . ?
O1 C9 1.444(2) . ?
O2 C9 1.4044(19) . ?
O2 C10 1.4378(19) . ?
C1 C2 1.377(3) . ?
C1 C6 1.388(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.386(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(3) . ?
C6 C7 1.504(2) . ?
C7 C8 1.517(2) . ?
C7 C11 1.536(2) . ?
C7 H7A 0.9800 . ?
C8 C9 1.514(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C19 1.512(2) . ?
C10 C11 1.514(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.533(2) . ?
C11 H11A 0.9800 . ?
C12 C13 1.507(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.370(3) . ?
C13 C18 1.382(3) . ?
C14 C15 1.379(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.365(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.353(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.366(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.376(3) . ?
C19 C24 1.382(3) . ?
C20 C21 1.382(3) . ?
C20 H20A 0.9300 . ?
C21 C22 1.366(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.376(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.384(3) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?

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
C5 O1 C9 119.20(12) . . ?
C9 O2 C10 114.81(12) . . ?
C2 C1 C6 121.6(2) . . ?
C2 C1 H1A 119.2 . . ?
C6 C1 H1A 119.2 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
O1 C5 C4 115.86(16) . . ?
O1 C5 C6 122.67(15) . . ?
C4 C5 C6 121.47(17) . . ?
C1 C6 C5 117.19(18) . . ?
C1 C6 C7 123.86(17) . . ?
C5 C6 C7 118.91(16) . . ?
C6 C7 C8 107.32(14) . . ?
C6 C7 C11 113.23(15) . . ?
C8 C7 C11 107.98(14) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C11 C7 H7A 109.4 . . ?
C9 C8 C7 108.35(14) . . ?
C9 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O2 C9 O1 109.34(12) . . ?
O2 C9 C19 107.66(13) . . ?
O1 C9 C19 105.80(13) . . ?
O2 C9 C8 110.41(13) . . ?
O1 C9 C8 110.84(14) . . ?
C19 C9 C8 112.62(13) . . ?
O2 C10 C11 113.37(14) . . ?
O2 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
O2 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 111.22(15) . . ?
C10 C11 C7 109.16(14) . . ?
C12 C11 C7 113.68(14) . . ?
C10 C11 H11A 107.5 . . ?
C12 C11 H11A 107.5 . . ?
C7 C11 H11A 107.5 . . ?
C13 C12 C11 113.16(14) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C18 117.65(19) . . ?
C14 C13 C12 119.79(18) . . ?
C18 C13 C12 122.56(19) . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C17 C18 C13 121.2(2) . . ?
C17 C18 H18A 119.4 . . ?
C13 C18 H18A 119.4 . . ?
C20 C19 C24 118.68(19) . . ?
C20 C19 C9 121.94(17) . . ?
C24 C19 C9 119.31(18) . . ?
C19 C20 C21 120.9(2) . . ?
C19 C20 H20A 119.5 . . ?
C21 C20 H20A 119.5 . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21A 119.8 . . ?
C20 C21 H21A 119.8 . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22A 120.4 . . ?
C23 C22 H22A 120.4 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23A 119.7 . . ?
C24 C23 H23A 119.7 . . ?
C19 C24 C23 120.2(2) . . ?
C19 C24 H24A 119.9 . . ?
C23 C24 H24A 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
C6 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C9 O1 C5 C4 174.29(16) . . . . ?
C9 O1 C5 C6 -5.6(2) . . . . ?
C3 C4 C5 O1 179.02(19) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 178.1(2) . . . . ?
O1 C5 C6 C1 -179.37(17) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
O1 C5 C6 C7 2.8(3) . . . . ?
C4 C5 C6 C7 -177.11(18) . . . . ?
C1 C6 C7 C8 -146.89(19) . . . . ?
C5 C6 C7 C8 30.8(2) . . . . ?
C1 C6 C7 C11 94.0(2) . . . . ?
C5 C6 C7 C11 -88.2(2) . . . . ?
C6 C7 C8 C9 -60.74(18) . . . . ?
C11 C7 C8 C9 61.64(17) . . . . ?
C10 O2 C9 O1 -65.69(16) . . . . ?
C10 O2 C9 C19 179.81(13) . . . . ?
C10 O2 C9 C8 56.51(17) . . . . ?
C5 O1 C9 O2 95.67(16) . . . . ?
C5 O1 C9 C19 -148.64(14) . . . . ?
C5 O1 C9 C8 -26.3(2) . . . . ?
C7 C8 C9 O2 -61.37(18) . . . . ?
C7 C8 C9 O1 59.95(17) . . . . ?
C7 C8 C9 C19 178.26(14) . . . . ?
C9 O2 C10 C11 -52.27(18) . . . . ?
O2 C10 C11 C12 177.34(13) . . . . ?
O2 C10 C11 C7 51.12(19) . . . . ?
C6 C7 C11 C10 62.24(19) . . . . ?
C8 C7 C11 C10 -56.44(17) . . . . ?
C6 C7 C11 C12 -62.6(2) . . . . ?
C8 C7 C11 C12 178.76(14) . . . . ?
C10 C11 C12 C13 73.6(2) . . . . ?
C7 C11 C12 C13 -162.73(16) . . . . ?
C11 C12 C13 C14 89.7(2) . . . . ?
C11 C12 C13 C18 -89.7(2) . . . . ?
C18 C13 C14 C15 -0.9(3) . . . . ?
C12 C13 C14 C15 179.6(2) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 -1.8(4) . . . . ?
C16 C17 C18 C13 1.6(4) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C12 C13 C18 C17 179.17(19) . . . . ?
O2 C9 C19 C20 -15.2(2) . . . . ?
O1 C9 C19 C20 -132.06(16) . . . . ?
C8 C9 C19 C20 106.72(18) . . . . ?
O2 C9 C19 C24 167.80(15) . . . . ?
O1 C9 C19 C24 50.97(19) . . . . ?
C8 C9 C19 C24 -70.3(2) . . . . ?
C24 C19 C20 C21 -1.4(3) . . . . ?
C9 C19 C20 C21 -178.41(17) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C20 C19 C24 C23 0.8(3) . . . . ?
C9 C19 C24 C23 177.85(16) . . . . ?
C22 C23 C24 C19 0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        68.10
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.024
