# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_wcy001_0m
_database_code_depnum_ccdc_archive 'CCDC 2122614'
loop_
_audit_author_name
_audit_author_address
'Jiang-Xi Yu'
;Hengyang Normal University
China
;
_audit_update_record             
;
2021-11-17 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
6a-methyl-11-phenyl-6,6a-dihydro-5H-benzo[a]fluoren-5-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 O'
_chemical_formula_weight         322.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.188(12)
_cell_length_b                   19.18(2)
_cell_length_c                   9.426(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.733(16)
_cell_angle_gamma                90
_cell_volume                     1661(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7446
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.81
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   0.982
_exptl_transmission_factor_max   0.984
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            17892
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         26.001
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3204
_reflns_number_gt                2690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2016/6 (Sheldrick, 2016)'
_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)+(0.0464P)²+0.5211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3204
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 -0.28989(15) 0.40762(7) 0.45238(16) 0.0745(4) Uani 1 1 d . . . . .
C1 C -0.19603(18) 0.37581(9) 0.39035(17) 0.0502(4) Uani 1 1 d . . . . .
C2 C -0.05141(18) 0.40862(8) 0.36101(17) 0.0488(4) Uani 1 1 d . . . . .
H2A H 0.017116 0.396399 0.436097 0.059 Uiso 1 1 calc R U . . .
H2B H -0.061737 0.458947 0.360114 0.059 Uiso 1 1 calc R U . . .
C3 C 0.00749(16) 0.38435(7) 0.21911(15) 0.0393(3) Uani 1 1 d . . . . .
C4 C 0.16296(16) 0.40412(7) 0.19365(15) 0.0389(3) Uani 1 1 d . . . . .
C5 C 0.22597(18) 0.46877(8) 0.18683(17) 0.0491(4) Uani 1 1 d . . . . .
H5 H 0.170687 0.508818 0.199958 0.059 Uiso 1 1 calc R U . . .
C6 C 0.37269(19) 0.47333(9) 0.1602(2) 0.0571(4) Uani 1 1 d . . . . .
H6 H 0.416894 0.516865 0.155177 0.069 Uiso 1 1 calc R U . . .
C7 C 0.45436(18) 0.41415(9) 0.1409(2) 0.0556(4) Uani 1 1 d . . . . .
H7 H 0.553340 0.418212 0.123167 0.067 Uiso 1 1 calc R U . . .
C8 C 0.39182(16) 0.34856(8) 0.14733(16) 0.0451(4) Uani 1 1 d . . . . .
H8 H 0.447531 0.308629 0.134507 0.054 Uiso 1 1 calc R U . . .
C9 C 0.24448(15) 0.34401(7) 0.17334(14) 0.0364(3) Uani 1 1 d . . . . .
C10 C 0.14973(15) 0.28309(7) 0.19139(14) 0.0346(3) Uani 1 1 d . . . . .
C11 C 0.01452(15) 0.30573(7) 0.22078(14) 0.0360(3) Uani 1 1 d . . . . .
C12 C -0.11832(15) 0.26860(7) 0.25936(15) 0.0391(3) Uani 1 1 d . . . . .
C13 C -0.15009(17) 0.20107(8) 0.21509(17) 0.0475(4) Uani 1 1 d . . . . .
H13 H -0.083309 0.176855 0.160527 0.057 Uiso 1 1 calc R U . . .
C14 C -0.27938(19) 0.16955(9) 0.25109(19) 0.0556(4) Uani 1 1 d . . . . .
H14 H -0.299687 0.124704 0.218974 0.067 Uiso 1 1 calc R U . . .
C15 C -0.37815(19) 0.20365(10) 0.3337(2) 0.0592(5) Uani 1 1 d . . . . .
H15 H -0.464504 0.181832 0.358661 0.071 Uiso 1 1 calc R U . . .
C16 C -0.34928(18) 0.26954(10) 0.37887(19) 0.0569(4) Uani 1 1 d . . . . .
H16 H -0.416143 0.292466 0.435576 0.068 Uiso 1 1 calc R U . . .
C17 C -0.22098(16) 0.30330(8) 0.34157(16) 0.0454(4) Uani 1 1 d . . . . .
C18 C -0.08998(18) 0.41049(9) 0.09799(18) 0.0516(4) Uani 1 1 d . . . . .
H18A H -0.189012 0.397495 0.115639 0.077 Uiso 1 1 calc R U . . .
H18B H -0.082993 0.460330 0.091811 0.077 Uiso 1 1 calc R U . . .
H18C H -0.059228 0.390077 0.010348 0.077 Uiso 1 1 calc R U . . .
C19 C 0.20531(14) 0.21093(7) 0.18423(14) 0.0360(3) Uani 1 1 d . . . . .
C20 C 0.27686(16) 0.18729(8) 0.06506(16) 0.0440(4) Uani 1 1 d . . . . .
H20 H 0.289343 0.217234 -0.011420 0.053 Uiso 1 1 calc R U . . .
C21 C 0.32957(18) 0.12061(9) 0.05784(19) 0.0541(4) Uani 1 1 d . . . . .
H21 H 0.376135 0.105408 -0.023535 0.065 Uiso 1 1 calc R U . . .
C22 C 0.31358(19) 0.07618(8) 0.1710(2) 0.0576(5) Uani 1 1 d . . . . .
H22 H 0.348586 0.030761 0.166111 0.069 Uiso 1 1 calc R U . . .
C23 C 0.2464(2) 0.09889(8) 0.29006(19) 0.0539(4) Uani 1 1 d . . . . .
H23 H 0.237579 0.069173 0.367430 0.065 Uiso 1 1 calc R U . . .
C24 C 0.19120(17) 0.16572(8) 0.29699(16) 0.0433(4) Uani 1 1 d . . . . .
H24 H 0.144055 0.180391 0.378443 0.052 Uiso 1 1 calc R U . . .


_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 1.213(2) . ?
C1 C17 1.482(3) . ?
C1 C2 1.499(3) . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.500(3) . ?
C3 C11 1.510(3) . ?
C3 C18 1.527(2) . ?
C4 C5 1.371(3) . ?
C4 C9 1.389(2) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.468(2) . ?
C10 C11 1.348(2) . ?
C10 C19 1.477(2) . ?
C11 C12 1.463(2) . ?
C12 C13 1.391(3) . ?
C12 C17 1.397(2) . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(3) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.379(2) . ?
C19 C20 1.385(2) . ?
C20 C21 1.370(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.359(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9300 . ?
C24 H24 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
O1 C1 C17 120.91(16) . . ?
O1 C1 C2 121.01(18) . . ?
C17 C1 C2 118.08(13) . . ?
C1 C2 C3 111.07(14) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C11 102.33(11) . . ?
C4 C3 C2 114.41(13) . . ?
C11 C3 C2 108.18(12) . . ?
C4 C3 C18 110.36(14) . . ?
C11 C3 C18 111.13(13) . . ?
C2 C3 C18 110.18(15) . . ?
C5 C4 C9 121.04(16) . . ?
C5 C4 C3 129.78(13) . . ?
C9 C4 C3 109.17(14) . . ?
C4 C5 C6 118.76(15) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.60(16) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.14(17) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 118.25(15) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C4 120.21(14) . . ?
C8 C9 C10 130.89(14) . . ?
C4 C9 C10 108.84(15) . . ?
C11 C10 C9 108.47(14) . . ?
C11 C10 C19 129.14(13) . . ?
C9 C10 C19 122.32(14) . . ?
C10 C11 C12 131.93(15) . . ?
C10 C11 C3 111.04(12) . . ?
C12 C11 C3 116.95(13) . . ?
C13 C12 C17 118.00(15) . . ?
C13 C12 C11 123.46(14) . . ?
C17 C12 C11 118.51(15) . . ?
C14 C13 C12 120.84(16) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.64(18) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.63(16) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.01(17) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 119.86(17) . . ?
C16 C17 C1 119.05(15) . . ?
C12 C17 C1 121.09(14) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.00(15) . . ?
C24 C19 C10 121.20(14) . . ?
C20 C19 C10 120.77(13) . . ?
C21 C20 C19 121.18(15) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.94(17) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.74(17) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.50(16) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 120.61(16) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?

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 -145.02(16) . . . . ?
C17 C1 C2 C3 35.1(2) . . . . ?
C1 C2 C3 C4 -169.32(13) . . . . ?
C1 C2 C3 C11 -56.01(17) . . . . ?
C1 C2 C3 C18 65.65(19) . . . . ?
C11 C3 C4 C5 -177.22(15) . . . . ?
C2 C3 C4 C5 -60.5(2) . . . . ?
C18 C3 C4 C5 64.4(2) . . . . ?
C11 C3 C4 C9 3.84(15) . . . . ?
C2 C3 C4 C9 120.57(14) . . . . ?
C18 C3 C4 C9 -114.50(15) . . . . ?
C9 C4 C5 C6 -0.4(2) . . . . ?
C3 C4 C5 C6 -179.23(15) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C4 -0.6(2) . . . . ?
C7 C8 C9 C10 -177.37(15) . . . . ?
C5 C4 C9 C8 0.7(2) . . . . ?
C3 C4 C9 C8 179.79(13) . . . . ?
C5 C4 C9 C10 178.14(13) . . . . ?
C3 C4 C9 C10 -2.81(16) . . . . ?
C8 C9 C10 C11 177.45(14) . . . . ?
C4 C9 C10 C11 0.42(16) . . . . ?
C8 C9 C10 C19 0.4(2) . . . . ?
C4 C9 C10 C19 -176.62(12) . . . . ?
C9 C10 C11 C12 -174.35(14) . . . . ?
C19 C10 C11 C12 2.4(3) . . . . ?
C9 C10 C11 C3 2.15(16) . . . . ?
C19 C10 C11 C3 178.93(13) . . . . ?
C4 C3 C11 C10 -3.66(15) . . . . ?
C2 C3 C11 C10 -124.79(13) . . . . ?
C18 C3 C11 C10 114.13(15) . . . . ?
C4 C3 C11 C12 173.42(12) . . . . ?
C2 C3 C11 C12 52.29(17) . . . . ?
C18 C3 C11 C12 -68.79(18) . . . . ?
C10 C11 C12 C13 -29.6(2) . . . . ?
C3 C11 C12 C13 154.06(14) . . . . ?
C10 C11 C12 C17 152.32(16) . . . . ?
C3 C11 C12 C17 -24.01(19) . . . . ?
C17 C12 C13 C14 0.2(2) . . . . ?
C11 C12 C13 C14 -177.87(14) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C12 -1.6(3) . . . . ?
C15 C16 C17 C1 178.44(16) . . . . ?
C13 C12 C17 C16 1.2(2) . . . . ?
C11 C12 C17 C16 179.37(14) . . . . ?
C13 C12 C17 C1 -178.83(14) . . . . ?
C11 C12 C17 C1 -0.7(2) . . . . ?
O1 C1 C17 C16 -5.7(2) . . . . ?
C2 C1 C17 C16 174.20(15) . . . . ?
O1 C1 C17 C12 174.33(16) . . . . ?
C2 C1 C17 C12 -5.8(2) . . . . ?
C11 C10 C19 C24 -55.2(2) . . . . ?
C9 C10 C19 C24 121.20(15) . . . . ?
C11 C10 C19 C20 126.60(16) . . . . ?
C9 C10 C19 C20 -57.01(19) . . . . ?
C24 C19 C20 C21 1.3(2) . . . . ?
C10 C19 C20 C21 179.58(14) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C24 1.5(3) . . . . ?
C20 C19 C24 C23 -0.3(2) . . . . ?
C10 C19 C24 C23 -178.59(14) . . . . ?
C22 C23 C24 C19 -1.1(2) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.031

