# 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_bettoni4_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2019645'
loop_
_audit_author_name
_audit_author_address
'Jean-Francois Lohier'
;LCMT ENSICAEN
France
;
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
(2,3,4,5,6-pentamethylphenyl)(1,8,8-trimethylbicyclo[3.2.1]octan-3-yl)methanone
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H34 O'
_chemical_formula_sum            'C23 H34 O'
_chemical_formula_weight         326.50

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           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                   6.689(4)
_cell_length_b                   10.950(6)
_cell_length_c                   13.040(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.67(5)
_cell_angle_gamma                90
_cell_volume                     952.0(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5155
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      33.46

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   0.4847
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Sadabs 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6469
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.432
_diffrn_reflns_theta_max         25.642
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.852
_reflns_number_total             3024
_reflns_number_gt                1928
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     0.726
_reflns_Friedel_fraction_full    0.738

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0435P)²] 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_abs_structure_details 
;
 Flack x determined using 616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.1(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3024
_refine_ls_number_parameters     225
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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 0.5513(5) 0.6834(3) 0.2628(3) 0.0352(10) Uani 1 1 d . . . . .
C14 C 0.1805(7) 0.6790(4) 0.4010(3) 0.0207(12) Uani 1 1 d . . . . .
C15 C 0.0937(7) 0.6831(4) 0.4937(4) 0.0203(11) Uani 1 1 d . . . . .
C12 C 0.4491(8) 0.5995(4) 0.2924(4) 0.0228(12) Uani 1 1 d . . . . .
C1 C 0.4107(7) 0.4858(4) 0.2280(4) 0.0216(11) Uani 1 1 d . . . . .
H1 H 0.470301 0.416525 0.270011 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1815(8) 0.6200(4) 0.5793(4) 0.0218(12) Uani 1 1 d . . . . .
C19 C 0.0900(8) 0.7502(4) 0.3087(4) 0.0308(13) Uani 1 1 d . . . . .
H19A H -0.046796 0.721233 0.290122 0.046 Uiso 1 1 calc R U . . .
H19B H 0.171712 0.738056 0.250447 0.046 Uiso 1 1 calc R U . . .
H19C H 0.086717 0.837264 0.325839 0.046 Uiso 1 1 calc R U . . .
C13 C 0.3545(8) 0.6083(4) 0.3933(4) 0.0190(12) Uani 1 1 d . . . . .
C18 C 0.4414(7) 0.5441(4) 0.4779(4) 0.0219(12) Uani 1 1 d . . . . .
C3 C 0.4595(8) 0.3815(4) 0.0555(4) 0.0232(12) Uani 1 1 d . . . . .
C17 C 0.3563(8) 0.5504(4) 0.5715(4) 0.0238(13) Uani 1 1 d . . . . .
C5 C 0.1539(8) 0.3518(4) 0.1319(4) 0.0237(13) Uani 1 1 d . . . . .
H5 H 0.009303 0.327797 0.123229 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2316(8) 0.3850(4) 0.0267(4) 0.0217(12) Uani 1 1 d . . . . .
C23 C 0.6344(8) 0.4719(5) 0.4687(4) 0.0338(14) Uani 1 1 d . . . . .
H23A H 0.604911 0.384283 0.469427 0.051 Uiso 1 1 calc R U . . .
H23B H 0.731314 0.492029 0.526659 0.051 Uiso 1 1 calc R U . . .
H23C H 0.690986 0.493166 0.404000 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1527(8) 0.5069(4) -0.0184(4) 0.0315(14) Uani 1 1 d . . . . .
H11A H 0.006028 0.503872 -0.028953 0.047 Uiso 1 1 calc R U . . .
H11B H 0.208904 0.521501 -0.084381 0.047 Uiso 1 1 calc R U . . .
H11C H 0.192747 0.573215 0.029427 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5206(7) 0.4887(4) 0.1296(4) 0.0248(12) Uani 1 1 d . . . . .
H2A H 0.666908 0.485000 0.148235 0.030 Uiso 1 1 calc R U . . .
H2B H 0.491198 0.566962 0.093481 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2868(8) 0.2410(4) 0.1671(4) 0.0302(13) Uani 1 1 d . . . . .
H8A H 0.311185 0.239223 0.242950 0.036 Uiso 1 1 calc R U . . .
H8B H 0.222203 0.163433 0.143650 0.036 Uiso 1 1 calc R U . . .
C20 C -0.0927(8) 0.7588(4) 0.5025(4) 0.0331(13) Uani 1 1 d . . . . .
H20A H -0.054592 0.843861 0.517045 0.050 Uiso 1 1 calc R U . . .
H20B H -0.166922 0.726977 0.558494 0.050 Uiso 1 1 calc R U . . .
H20C H -0.177553 0.754742 0.437686 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1855(7) 0.4574(4) 0.2086(4) 0.0258(13) Uani 1 1 d . . . . .
H6A H 0.130395 0.435063 0.274227 0.031 Uiso 1 1 calc R U . . .
H6B H 0.113497 0.530784 0.180856 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4842(8) 0.2607(5) 0.1163(4) 0.0323(14) Uani 1 1 d . . . . .
H7A H 0.508643 0.192116 0.069438 0.039 Uiso 1 1 calc R U . . .
H7B H 0.598589 0.266264 0.169235 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1661(8) 0.2860(4) -0.0540(4) 0.0301(14) Uani 1 1 d . . . . .
H10A H 0.019532 0.285408 -0.065636 0.045 Uiso 1 1 calc R U . . .
H10B H 0.212695 0.205785 -0.028607 0.045 Uiso 1 1 calc R U . . .
H10C H 0.224761 0.303996 -0.118773 0.045 Uiso 1 1 calc R U . . .
C21 C 0.0882(10) 0.6298(5) 0.6810(4) 0.0376(15) Uani 1 1 d . . . . .
H21A H 0.052615 0.715106 0.693257 0.056 Uiso 1 1 calc R U . . .
H21B H 0.184507 0.601627 0.736633 0.056 Uiso 1 1 calc R U . . .
H21C H -0.032739 0.579119 0.678887 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5874(7) 0.3864(5) -0.0359(4) 0.0330(14) Uani 1 1 d . . . . .
H9A H 0.729520 0.380758 -0.011308 0.050 Uiso 1 1 calc R U . . .
H9B H 0.563003 0.463559 -0.072849 0.050 Uiso 1 1 calc R U . . .
H9C H 0.551989 0.317962 -0.082311 0.050 Uiso 1 1 calc R U . . .
C22 C 0.4464(8) 0.4785(5) 0.6631(4) 0.0357(14) Uani 1 1 d . . . . .
H22A H 0.513453 0.405608 0.638992 0.054 Uiso 1 1 calc R U . . .
H22B H 0.339815 0.453921 0.706130 0.054 Uiso 1 1 calc R U . . .
H22C H 0.544124 0.529480 0.703481 0.054 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 C12 1.226(6) . ?
C14 C15 1.383(6) . ?
C14 C13 1.409(7) . ?
C14 C19 1.518(6) . ?
C15 C16 1.400(6) . ?
C15 C20 1.509(6) . ?
C12 C13 1.508(7) . ?
C12 C1 1.512(6) . ?
C1 C2 1.530(6) . ?
C1 C6 1.538(7) . ?
C1 H1 1.0000 . ?
C16 C17 1.407(7) . ?
C16 C21 1.515(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13 C18 1.394(6) . ?
C18 C17 1.390(7) . ?
C18 C23 1.527(7) . ?
C3 C9 1.524(6) . ?
C3 C4 1.541(7) . ?
C3 C7 1.543(7) . ?
C3 C2 1.554(6) . ?
C17 C22 1.514(7) . ?
C5 C6 1.532(6) . ?
C5 C4 1.549(7) . ?
C5 C8 1.551(7) . ?
C5 H5 1.0000 . ?
C4 C11 1.535(6) . ?
C4 C10 1.549(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C8 C7 1.540(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C15 C14 C13 119.2(4) . . ?
C15 C14 C19 120.5(5) . . ?
C13 C14 C19 120.3(4) . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 C20 119.5(4) . . ?
C16 C15 C20 120.3(4) . . ?
O1 C12 C13 120.7(4) . . ?
O1 C12 C1 121.0(4) . . ?
C13 C12 C1 118.2(4) . . ?
C12 C1 C2 112.2(4) . . ?
C12 C1 C6 112.2(4) . . ?
C2 C1 C6 113.4(4) . . ?
C12 C1 H1 106.1 . . ?
C2 C1 H1 106.1 . . ?
C6 C1 H1 106.1 . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 C21 119.2(5) . . ?
C17 C16 C21 120.4(5) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C13 C14 121.0(4) . . ?
C18 C13 C12 118.7(5) . . ?
C14 C13 C12 120.3(4) . . ?
C17 C18 C13 119.7(5) . . ?
C17 C18 C23 120.3(5) . . ?
C13 C18 C23 119.9(5) . . ?
C9 C3 C4 114.5(4) . . ?
C9 C3 C7 112.8(4) . . ?
C4 C3 C7 102.1(4) . . ?
C9 C3 C2 108.9(4) . . ?
C4 C3 C2 109.8(4) . . ?
C7 C3 C2 108.5(4) . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 C22 120.1(5) . . ?
C16 C17 C22 120.3(5) . . ?
C6 C5 C4 111.3(4) . . ?
C6 C5 C8 110.6(4) . . ?
C4 C5 C8 102.7(4) . . ?
C6 C5 H5 110.7 . . ?
C4 C5 H5 110.7 . . ?
C8 C5 H5 110.7 . . ?
C11 C4 C3 114.7(4) . . ?
C11 C4 C10 106.3(4) . . ?
C3 C4 C10 111.6(4) . . ?
C11 C4 C5 114.4(4) . . ?
C3 C4 C5 100.0(4) . . ?
C10 C4 C5 109.9(4) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 C3 112.7(4) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C7 C8 C5 104.7(4) . . ?
C7 C8 H8A 110.8 . . ?
C5 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C5 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C6 C1 109.9(4) . . ?
C5 C6 H6A 109.7 . . ?
C1 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C3 106.3(4) . . ?
C8 C7 H7A 110.5 . . ?
C3 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
C3 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049

