# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2163866'
loop_
_audit_author_name
_audit_author_address
'Tao Cai'
;shaoxing university
China
;
_audit_update_record             
;
2022-04-01 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20'
_chemical_formula_weight         296.39

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   5.66890(10)
_cell_length_b                   10.27550(10)
_cell_length_c                   27.4770(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1600.56(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5152
_cell_measurement_theta_min      3.1960
_cell_measurement_theta_max      73.8670

_exptl_crystal_description       block
_exptl_crystal_colour            colreless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35460
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6090
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         74.14
_reflns_number_total             2973
_reflns_number_gt                2890
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0452P)²+0.4078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(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   -0.7(18)
_refine_ls_number_reflns         2973
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C8 C 0.5774(2) 0.13402(13) 0.35533(5) 0.0243(3) Uani 1 1 d . . .
C12 C 0.4960(3) 0.05310(13) 0.31773(6) 0.0275(3) Uani 1 1 d . . .
C9 C 0.7610(3) 0.22359(13) 0.34710(5) 0.0238(3) Uani 1 1 d . . .
C10 C 0.8466(3) 0.30863(14) 0.38726(5) 0.0273(3) Uani 1 1 d . . .
C15 C 0.8689(3) 0.22980(13) 0.30062(5) 0.0272(3) Uani 1 1 d . . .
C2 C 0.6592(3) 0.06259(15) 0.43922(5) 0.0289(3) Uani 1 1 d . . .
C11 C 0.9028(3) 0.26395(16) 0.43181(6) 0.0300(3) Uani 1 1 d . . .
H11A H 0.9764 0.3243 0.4531 0.036 Uiso 1 1 calc R . .
C7 C 0.4789(3) 0.12437(14) 0.40621(5) 0.0277(3) Uani 1 1 d . . .
H7A H 0.4386 0.2123 0.4184 0.033 Uiso 1 1 calc R . .
H7B H 0.3332 0.0713 0.4059 0.033 Uiso 1 1 calc R . .
C16 C 0.8612(3) 0.45179(14) 0.37732(5) 0.0291(3) Uani 1 1 d . . .
C1A C 0.8634(3) 0.13256(16) 0.45129(5) 0.0299(3) Uani 1 1 d . . .
C17B C 0.6802(3) 0.51159(14) 0.35141(6) 0.0317(3) Uani 1 1 d . . .
H17A H 0.5563 0.4600 0.3384 0.038 Uiso 1 1 calc R . .
C13C C 0.6004(3) 0.06313(14) 0.27239(6) 0.0322(3) Uani 1 1 d . . .
H13A H 0.5448 0.0104 0.2464 0.039 Uiso 1 1 calc R . .
C23D C 1.0777(3) 0.31593(14) 0.29011(6) 0.0342(4) Uani 1 1 d . . .
H23A H 1.1245 0.3057 0.2560 0.051 Uiso 1 1 calc R . .
H23B H 1.2095 0.2912 0.3113 0.051 Uiso 1 1 calc R . .
H23C H 1.0350 0.4069 0.2962 0.051 Uiso 1 1 calc R . .
C14E C 0.7850(3) 0.14892(14) 0.26427(5) 0.0313(4) Uani 1 1 d . . .
H14A H 0.8558 0.1523 0.2329 0.038 Uiso 1 1 calc R . .
C18F C 0.6778(3) 0.64556(15) 0.34430(7) 0.0367(4) Uani 1 1 d . . .
H18A H 0.5525 0.6849 0.3267 0.044 Uiso 1 1 calc R . .
C6G C 1.0206(3) 0.07988(19) 0.48519(5) 0.0368(4) Uani 1 1 d . . .
H6GA H 1.1531 0.1296 0.4953 0.044 Uiso 1 1 calc R . .
C3H C 0.6271(3) -0.06144(17) 0.45851(6) 0.0362(4) Uani 1 1 d . . .
H3HA H 0.4918 -0.1106 0.4496 0.043 Uiso 1 1 calc R . .
C21I C 1.0434(3) 0.52911(16) 0.39543(7) 0.0367(4) Uani 1 1 d . . .
H21A H 1.1700 0.4902 0.4128 0.044 Uiso 1 1 calc R . .
C19J C 0.8581(3) 0.72164(15) 0.36290(7) 0.0401(4) Uani 1 1 d . . .
H19A H 0.8564 0.8133 0.3584 0.048 Uiso 1 1 calc R . .
C22K C 0.2955(3) -0.04171(15) 0.32557(6) 0.0360(4) Uani 1 1 d . . .
H22A H 0.2646 -0.0891 0.2953 0.054 Uiso 1 1 calc R . .
H22B H 0.1535 0.0061 0.3353 0.054 Uiso 1 1 calc R . .
H22C H 0.3384 -0.1036 0.3512 0.054 Uiso 1 1 calc R . .
C20L C 1.0402(3) 0.66339(17) 0.38809(7) 0.0424(4) Uani 1 1 d . . .
H20A H 1.1648 0.7154 0.4006 0.051 Uiso 1 1 calc R . .
C4M C 0.7903(3) -0.1140(2) 0.49053(6) 0.0458(5) Uani 1 1 d . . .
H4MA H 0.7670 -0.1992 0.5031 0.055 Uiso 1 1 calc R . .
C5N C 0.9870(3) -0.0432(2) 0.50429(6) 0.0459(5) Uani 1 1 d . . .
H5NA H 1.0977 -0.0787 0.5266 0.055 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
C8 C12 1.404(2) . ?
C8 C9 1.4078(19) . ?
C8 C7 1.509(2) . ?
C12 C13C 1.383(2) . ?
C12 C22K 1.512(2) . ?
C9 C15 1.417(2) . ?
C9 C10 1.489(2) . ?
C10 C11 1.345(2) . ?
C10 C16 1.498(2) . ?
C15 C14E 1.384(2) . ?
C15 C23D 1.506(2) . ?
C2 C3H 1.392(2) . ?
C2 C1A 1.402(2) . ?
C2 C7 1.507(2) . ?
C11 C1A 1.469(2) . ?
C11 H11A 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C16 C17B 1.392(2) . ?
C16 C21I 1.395(2) . ?
C1A C6G 1.398(2) . ?
C17B C18F 1.391(2) . ?
C17B H17A 0.9500 . ?
C13C C14E 1.386(2) . ?
C13C H13A 0.9500 . ?
C23D H23A 0.9800 . ?
C23D H23B 0.9800 . ?
C23D H23C 0.9800 . ?
C14E H14A 0.9500 . ?
C18F C19J 1.384(2) . ?
C18F H18A 0.9500 . ?
C6G C5N 1.382(3) . ?
C6G H6GA 0.9500 . ?
C3H C4M 1.386(2) . ?
C3H H3HA 0.9500 . ?
C21I C20L 1.395(2) . ?
C21I H21A 0.9500 . ?
C19J C20L 1.379(3) . ?
C19J H19A 0.9500 . ?
C22K H22A 0.9800 . ?
C22K H22B 0.9800 . ?
C22K H22C 0.9800 . ?
C20L H20A 0.9500 . ?
C4M C5N 1.384(3) . ?
C4M H4MA 0.9500 . ?
C5N H5NA 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
C12 C8 C9 120.80(13) . . ?
C12 C8 C7 121.41(12) . . ?
C9 C8 C7 117.74(13) . . ?
C13C C12 C8 118.54(13) . . ?
C13C C12 C22K 119.87(14) . . ?
C8 C12 C22K 121.58(14) . . ?
C8 C9 C15 119.54(13) . . ?
C8 C9 C10 120.38(13) . . ?
C15 C9 C10 120.06(13) . . ?
C11 C10 C9 123.44(14) . . ?
C11 C10 C16 119.19(13) . . ?
C9 C10 C16 117.33(13) . . ?
C14E C15 C9 118.39(13) . . ?
C14E C15 C23D 118.98(14) . . ?
C9 C15 C23D 122.57(14) . . ?
C3H C2 C1A 119.16(15) . . ?
C3H C2 C7 121.74(14) . . ?
C1A C2 C7 119.09(13) . . ?
C10 C11 C1A 127.52(14) . . ?
C10 C11 H11A 116.2 . . ?
C1A C11 H11A 116.2 . . ?
C2 C7 C8 109.54(12) . . ?
C2 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C2 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C17B C16 C21I 118.49(14) . . ?
C17B C16 C10 119.06(13) . . ?
C21I C16 C10 122.34(15) . . ?
C6G C1A C2 119.03(15) . . ?
C6G C1A C11 120.10(15) . . ?
C2 C1A C11 120.68(14) . . ?
C18F C17B C16 121.07(15) . . ?
C18F C17B H17A 119.5 . . ?
C16 C17B H17A 119.5 . . ?
C12 C13C C14E 121.02(14) . . ?
C12 C13C H13A 119.5 . . ?
C14E C13C H13A 119.5 . . ?
C15 C23D H23A 109.5 . . ?
C15 C23D H23B 109.5 . . ?
H23A C23D H23B 109.5 . . ?
C15 C23D H23C 109.5 . . ?
H23A C23D H23C 109.5 . . ?
H23B C23D H23C 109.5 . . ?
C15 C14E C13C 121.67(14) . . ?
C15 C14E H14A 119.2 . . ?
C13C C14E H14A 119.2 . . ?
C19J C18F C17B 120.00(16) . . ?
C19J C18F H18A 120.0 . . ?
C17B C18F H18A 120.0 . . ?
C5N C6G C1A 121.27(16) . . ?
C5N C6G H6GA 119.4 . . ?
C1A C6G H6GA 119.4 . . ?
C4M C3H C2 120.72(16) . . ?
C4M C3H H3HA 119.6 . . ?
C2 C3H H3HA 119.6 . . ?
C20L C21I C16 120.13(17) . . ?
C20L C21I H21A 119.9 . . ?
C16 C21I H21A 119.9 . . ?
C20L C19J C18F 119.51(15) . . ?
C20L C19J H19A 120.2 . . ?
C18F C19J H19A 120.2 . . ?
C12 C22K H22A 109.5 . . ?
C12 C22K H22B 109.5 . . ?
H22A C22K H22B 109.5 . . ?
C12 C22K H22C 109.5 . . ?
H22A C22K H22C 109.5 . . ?
H22B C22K H22C 109.5 . . ?
C19J C20L C21I 120.79(16) . . ?
C19J C20L H20A 119.6 . . ?
C21I C20L H20A 119.6 . . ?
C5N C4M C3H 120.41(17) . . ?
C5N C4M H4MA 119.8 . . ?
C3H C4M H4MA 119.8 . . ?
C6G C5N C4M 119.23(16) . . ?
C6G C5N H5NA 120.4 . . ?
C4M C5N H5NA 120.4 . . ?

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
C9 C8 C12 C13C 0.1(2) . . . . ?
C7 C8 C12 C13C -177.35(13) . . . . ?
C9 C8 C12 C22K -178.69(13) . . . . ?
C7 C8 C12 C22K 3.9(2) . . . . ?
C12 C8 C9 C15 -1.59(19) . . . . ?
C7 C8 C9 C15 175.95(13) . . . . ?
C12 C8 C9 C10 -179.80(13) . . . . ?
C7 C8 C9 C10 -2.26(19) . . . . ?
C8 C9 C10 C11 48.9(2) . . . . ?
C15 C9 C10 C11 -129.25(15) . . . . ?
C8 C9 C10 C16 -128.75(14) . . . . ?
C15 C9 C10 C16 53.05(19) . . . . ?
C8 C9 C15 C14E 1.6(2) . . . . ?
C10 C9 C15 C14E 179.78(13) . . . . ?
C8 C9 C15 C23D -175.40(13) . . . . ?
C10 C9 C15 C23D 2.8(2) . . . . ?
C9 C10 C11 C1A -8.6(2) . . . . ?
C16 C10 C11 C1A 169.02(14) . . . . ?
C3H C2 C7 C8 -110.87(16) . . . . ?
C1A C2 C7 C8 69.94(17) . . . . ?
C12 C8 C7 C2 107.51(15) . . . . ?
C9 C8 C7 C2 -70.01(16) . . . . ?
C11 C10 C16 C17B -136.50(15) . . . . ?
C9 C10 C16 C17B 41.3(2) . . . . ?
C11 C10 C16 C21I 39.8(2) . . . . ?
C9 C10 C16 C21I -142.37(15) . . . . ?
C3H C2 C1A C6G -4.7(2) . . . . ?
C7 C2 C1A C6G 174.53(14) . . . . ?
C3H C2 C1A C11 -179.71(14) . . . . ?
C7 C2 C1A C11 -0.5(2) . . . . ?
C10 C11 C1A C6G 148.25(16) . . . . ?
C10 C11 C1A C2 -36.8(2) . . . . ?
C21I C16 C17B C18F -1.1(2) . . . . ?
C10 C16 C17B C18F 175.40(15) . . . . ?
C8 C12 C13C C14E 1.4(2) . . . . ?
C22K C12 C13C C14E -179.77(14) . . . . ?
C9 C15 C14E C13C -0.1(2) . . . . ?
C23D C15 C14E C13C 177.00(13) . . . . ?
C12 C13C C14E C15 -1.5(2) . . . . ?
C16 C17B C18F C19J 0.4(3) . . . . ?
C2 C1A C6G C5N 4.6(2) . . . . ?
C11 C1A C6G C5N 179.65(15) . . . . ?
C1A C2 C3H C4M 2.1(2) . . . . ?
C7 C2 C3H C4M -177.09(16) . . . . ?
C17B C16 C21I C20L 0.9(2) . . . . ?
C10 C16 C21I C20L -175.42(16) . . . . ?
C17B C18F C19J C20L 0.5(3) . . . . ?
C18F C19J C20L C21I -0.7(3) . . . . ?
C16 C21I C20L C19J -0.1(3) . . . . ?
C2 C3H C4M C5N 0.7(3) . . . . ?
C1A C6G C5N C4M -1.8(3) . . . . ?
C3H C4M C5N C6G -0.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        74.14
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
