# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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 2293144'
loop_
_audit_author_name
_audit_author_address
'Jinyuan Wang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-09-06 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(1R,4S)-6-chloro-1,2,3,4,4a,9a-hexahydro-9H-1,4-methanofluoren-9-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Cl O'
_chemical_formula_weight         232.69

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.9459(11)
_cell_length_b                   9.3739(15)
_cell_length_c                   9.7165(15)
_cell_angle_alpha                66.321(2)
_cell_angle_beta                 76.356(2)
_cell_angle_gamma                88.872(2)
_cell_volume                     561.03(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4371
_cell_measurement_theta_min      2.363
_cell_measurement_theta_max      27.180

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.314
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   none
_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_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            4371
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         27.180
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2205
_reflns_number_gt                1828
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0451P)²+0.1522P] 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         2205
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
C1 C 0.6727(3) -0.2311(2) 0.4922(2) 0.0467(4) Uani 1 1 d . . . . .
H1 H 0.688409 -0.326433 0.568814 0.056 Uiso 1 1 calc R U . . .
C2 C 0.8287(3) -0.1179(2) 0.4161(2) 0.0452(4) Uani 1 1 d . . . . .
H2 H 0.950707 -0.134697 0.441281 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8007(2) 0.02269(19) 0.30041(18) 0.0357(4) Uani 1 1 d . . . . .
C4 C 0.6180(2) 0.05074(18) 0.26369(17) 0.0321(3) Uani 1 1 d . . . . .
C5 C 0.4594(2) -0.06205(18) 0.34112(17) 0.0363(4) Uani 1 1 d . . . . .
H5 H 0.336067 -0.044485 0.318381 0.044 Uiso 1 1 calc R U . . .
C6 C 0.4911(3) -0.20214(19) 0.45379(18) 0.0401(4) Uani 1 1 d . . . . .
C7 C 0.9453(2) 0.1586(2) 0.19888(19) 0.0383(4) Uani 1 1 d . . . . .
C8 C 0.8405(2) 0.27946(19) 0.08845(19) 0.0367(4) Uani 1 1 d . . . . .
H8 H 0.846442 0.380064 0.096612 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6224(2) 0.20917(17) 0.13338(17) 0.0316(3) Uani 1 1 d . . . . .
H9 H 0.527278 0.274977 0.166049 0.038 Uiso 1 1 calc R U . . .
C10 C 0.9170(3) 0.2986(2) -0.0808(2) 0.0457(4) Uani 1 1 d . . . . .
H10 H 1.061993 0.304210 -0.117025 0.055 Uiso 1 1 calc R U . . .
C11 C 0.8182(3) 0.4351(2) -0.1828(2) 0.0563(5) Uani 1 1 d . . . . .
H11A H 0.877403 0.462839 -0.292140 0.068 Uiso 1 1 calc R U . . .
H11B H 0.828939 0.526282 -0.160714 0.068 Uiso 1 1 calc R U . . .
C12 C 0.5986(3) 0.3690(2) -0.1366(2) 0.0443(4) Uani 1 1 d . . . . .
H12A H 0.510717 0.428716 -0.090953 0.053 Uiso 1 1 calc R U . . .
H12B H 0.557677 0.369846 -0.225686 0.053 Uiso 1 1 calc R U . . .
C13 C 0.5993(2) 0.20126(18) -0.01735(18) 0.0346(4) Uani 1 1 d . . . . .
H13 H 0.488828 0.129299 -0.003440 0.042 Uiso 1 1 calc R U . . .
C14 C 0.8051(3) 0.1589(2) -0.0798(2) 0.0427(4) Uani 1 1 d . . . . .
H14A H 0.822706 0.161014 -0.182722 0.051 Uiso 1 1 calc R U . . .
H14B H 0.838048 0.059247 -0.009987 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 0.29528(8) -0.34712(6) 0.55256(5) 0.05924(19) Uani 1 1 d . . . . .
O1 O 1.11851(18) 0.17161(16) 0.19942(16) 0.0564(4) Uani 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
C1 C2 1.373(3) . ?
C1 C6 1.389(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(2) . ?
C3 C7 1.476(2) . ?
C4 C5 1.383(2) . ?
C4 C9 1.511(2) . ?
C5 C6 1.385(2) . ?
C5 H5 0.9300 . ?
C6 Cl1 1.7401(17) . ?
C7 O1 1.2132(19) . ?
C7 C8 1.524(2) . ?
C8 C10 1.541(2) . ?
C8 C9 1.554(2) . ?
C8 H8 0.9800 . ?
C9 C13 1.541(2) . ?
C9 H9 0.9800 . ?
C10 C14 1.532(2) . ?
C10 C11 1.536(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.549(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.534(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.527(2) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C2 C1 C6 119.46(15) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C1 C2 C3 118.73(16) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.29(15) . . ?
C4 C3 C7 109.66(14) . . ?
C2 C3 C7 129.05(15) . . ?
C5 C4 C3 120.32(14) . . ?
C5 C4 C9 127.37(14) . . ?
C3 C4 C9 112.29(13) . . ?
C4 C5 C6 117.56(15) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 122.63(15) . . ?
C5 C6 Cl1 118.76(13) . . ?
C1 C6 Cl1 118.61(13) . . ?
O1 C7 C3 126.56(16) . . ?
O1 C7 C8 125.49(15) . . ?
C3 C7 C8 107.92(13) . . ?
C7 C8 C10 112.88(14) . . ?
C7 C8 C9 106.03(12) . . ?
C10 C8 C9 103.14(12) . . ?
C7 C8 H8 111.5 . . ?
C10 C8 H8 111.5 . . ?
C9 C8 H8 111.5 . . ?
C4 C9 C13 113.71(13) . . ?
C4 C9 C8 104.08(12) . . ?
C13 C9 C8 102.99(12) . . ?
C4 C9 H9 111.8 . . ?
C13 C9 H9 111.8 . . ?
C8 C9 H9 111.8 . . ?
C14 C10 C11 100.92(14) . . ?
C14 C10 C8 101.95(13) . . ?
C11 C10 C8 108.03(16) . . ?
C14 C10 H10 114.8 . . ?
C11 C10 H10 114.8 . . ?
C8 C10 H10 114.8 . . ?
C10 C11 C12 103.15(14) . . ?
C10 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C11 103.27(14) . . ?
C13 C12 H12A 111.1 . . ?
C11 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 C12 101.63(13) . . ?
C14 C13 C9 101.51(12) . . ?
C12 C13 C9 108.01(13) . . ?
C14 C13 H13 114.7 . . ?
C12 C13 H13 114.7 . . ?
C9 C13 H13 114.7 . . ?
C13 C14 C10 94.78(13) . . ?
C13 C14 H14A 112.8 . . ?
C10 C14 H14A 112.8 . . ?
C13 C14 H14B 112.8 . . ?
C10 C14 H14B 112.8 . . ?
H14A C14 H14B 110.2 . . ?

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 -0.9(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C1 C2 C3 C7 -177.44(17) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C7 C3 C4 C5 178.41(14) . . . . ?
C2 C3 C4 C9 -179.06(15) . . . . ?
C7 C3 C4 C9 -0.07(19) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C9 C4 C5 C6 177.64(15) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 Cl1 -179.58(12) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 Cl1 -179.68(14) . . . . ?
C4 C3 C7 O1 -179.21(17) . . . . ?
C2 C3 C7 O1 -0.3(3) . . . . ?
C4 C3 C7 C8 -0.95(19) . . . . ?
C2 C3 C7 C8 177.94(16) . . . . ?
O1 C7 C8 C10 67.6(2) . . . . ?
C3 C7 C8 C10 -110.67(15) . . . . ?
O1 C7 C8 C9 179.83(16) . . . . ?
C3 C7 C8 C9 1.54(17) . . . . ?
C5 C4 C9 C13 -66.0(2) . . . . ?
C3 C4 C9 C13 112.32(15) . . . . ?
C5 C4 C9 C8 -177.33(15) . . . . ?
C3 C4 C9 C8 1.02(17) . . . . ?
C7 C8 C9 C4 -1.52(16) . . . . ?
C10 C8 C9 C4 117.33(13) . . . . ?
C7 C8 C9 C13 -120.42(13) . . . . ?
C10 C8 C9 C13 -1.57(15) . . . . ?
C7 C8 C10 C14 80.41(16) . . . . ?
C9 C8 C10 C14 -33.56(16) . . . . ?
C7 C8 C10 C11 -173.78(14) . . . . ?
C9 C8 C10 C11 72.25(16) . . . . ?
C14 C10 C11 C12 36.39(18) . . . . ?
C8 C10 C11 C12 -70.14(18) . . . . ?
C10 C11 C12 C13 -1.63(19) . . . . ?
C11 C12 C13 C14 -33.89(17) . . . . ?
C11 C12 C13 C9 72.43(17) . . . . ?
C4 C9 C13 C14 -75.66(15) . . . . ?
C8 C9 C13 C14 36.29(14) . . . . ?
C4 C9 C13 C12 177.93(13) . . . . ?
C8 C9 C13 C12 -70.12(15) . . . . ?
C12 C13 C14 C10 55.42(15) . . . . ?
C9 C13 C14 C10 -55.94(14) . . . . ?
C11 C10 C14 C13 -56.31(15) . . . . ?
C8 C10 C14 C13 54.98(15) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044



