# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_RX
_database_code_depnum_ccdc_archive 'CCDC 2277624'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H16 O2'
_chemical_formula_sum            'C12 H16 O2'
_chemical_melting_point          ?


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         192.25

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 0.0096 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_chemical_absolute_configuration ad

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

_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.
;

_cell_length_a                   19.7972(5)
_cell_length_b                   5.6454(2)
_cell_length_c                   19.9238(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.7000(10)
_cell_angle_gamma                90
_cell_volume                     1989.31(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      66.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8628
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_process_details   'Bruker APEX2'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14782
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.482
_diffrn_reflns_theta_max         66.669
_diffrn_reflns_theta_full        66.669
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             3416
_reflns_number_gt                3233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.922

_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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0330P)²+0.6834P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00123(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(9)
_refine_ls_number_reflns         3416
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.62498(11) 0.4016(4) 0.17848(11) 0.0135(4) Uani 1 1 d . . . . .
H1 H 0.612282 0.305120 0.132249 0.016 Uiso 1 1 calc R U . . .
C2 C 0.70990(11) 0.4471(4) 0.21668(11) 0.0179(4) Uani 1 1 d . . . . .
H2A H 0.737321 0.294520 0.231548 0.022 Uiso 1 1 calc R U . . .
H2B H 0.723601 0.542598 0.262667 0.022 Uiso 1 1 calc R U . . .
C3 C 0.73313(12) 0.5791(4) 0.16323(12) 0.0198(5) Uani 1 1 d . . . . .
H3A H 0.787972 0.613790 0.189279 0.024 Uiso 1 1 calc R U . . .
H3B H 0.723404 0.477514 0.119314 0.024 Uiso 1 1 calc R U . . .
C4 C 0.68919(11) 0.8099(4) 0.13658(11) 0.0191(5) Uani 1 1 d . . . . .
H4A H 0.701956 0.885212 0.098864 0.023 Uiso 1 1 calc R U . . .
H4B H 0.704234 0.919753 0.179649 0.023 Uiso 1 1 calc R U . . .
C5 C 0.60374(11) 0.7672(4) 0.10184(10) 0.0153(4) Uani 1 1 d . . . . .
H5A H 0.587840 0.674564 0.054977 0.018 Uiso 1 1 calc R U . . .
H5B H 0.577207 0.921516 0.088536 0.018 Uiso 1 1 calc R U . . .
C6 C 0.58032(11) 0.6337(3) 0.15533(10) 0.0130(4) Uani 1 1 d . . . . .
C7 C 0.49476(11) 0.5971(3) 0.11784(11) 0.0144(4) Uani 1 1 d . . . . .
C8 C 0.44811(11) 0.7740(4) 0.12342(11) 0.0187(4) Uani 1 1 d . . . . .
H8 H 0.470005 0.915062 0.150449 0.022 Uiso 1 1 calc R U . . .
C9 C 0.36990(12) 0.7456(4) 0.08981(12) 0.0232(5) Uani 1 1 d . . . . .
H9 H 0.338944 0.867148 0.094231 0.028 Uiso 1 1 calc R U . . .
C10 C 0.33713(12) 0.5428(4) 0.05022(12) 0.0243(5) Uani 1 1 d . . . . .
H10 H 0.283802 0.523177 0.027829 0.029 Uiso 1 1 calc R U . . .
C11 C 0.38250(12) 0.3677(4) 0.04332(12) 0.0221(5) Uani 1 1 d . . . . .
H11 H 0.360185 0.228147 0.015554 0.027 Uiso 1 1 calc R U . . .
C12 C 0.46041(11) 0.3950(4) 0.07674(11) 0.0173(4) Uani 1 1 d . . . . .
H12 H 0.490869 0.273377 0.071481 0.021 Uiso 1 1 calc R U . . .
C13 C 0.50928(11) 0.3398(3) 0.34525(11) 0.0138(4) Uani 1 1 d . . . . .
H13 H 0.488196 0.254621 0.375664 0.017 Uiso 1 1 calc R U . . .
C14 C 0.44382(11) 0.3861(4) 0.26821(10) 0.0161(4) Uani 1 1 d . . . . .
H14A H 0.422506 0.233087 0.243460 0.019 Uiso 1 1 calc R U . . .
H14B H 0.462632 0.472041 0.236647 0.019 Uiso 1 1 calc R U . . .
C15 C 0.38199(11) 0.5315(4) 0.27437(11) 0.0188(4) Uani 1 1 d . . . . .
H15A H 0.342190 0.569569 0.223366 0.023 Uiso 1 1 calc R U . . .
H15B H 0.358609 0.436923 0.300263 0.023 Uiso 1 1 calc R U . . .
C16 C 0.41358(11) 0.7601(4) 0.31760(11) 0.0181(4) Uani 1 1 d . . . . .
H16A H 0.373469 0.842200 0.325381 0.022 Uiso 1 1 calc R U . . .
H16B H 0.429569 0.865676 0.287677 0.022 Uiso 1 1 calc R U . . .
C17 C 0.48102(11) 0.7124(4) 0.39378(11) 0.0155(4) Uani 1 1 d . . . . .
H17A H 0.463606 0.622648 0.425793 0.019 Uiso 1 1 calc R U . . .
H17B H 0.501871 0.865270 0.418917 0.019 Uiso 1 1 calc R U . . .
C18 C 0.54388(11) 0.5714(3) 0.38629(10) 0.0131(4) Uani 1 1 d . . . . .
C19 C 0.61048(11) 0.5324(4) 0.46376(11) 0.0151(4) Uani 1 1 d . . . . .
C20 C 0.61512(12) 0.3358(4) 0.50777(11) 0.0195(5) Uani 1 1 d . . . . .
H20 H 0.576400 0.219321 0.489112 0.023 Uiso 1 1 calc R U . . .
C21 C 0.67559(13) 0.3074(4) 0.57864(11) 0.0244(5) Uani 1 1 d . . . . .
H21 H 0.678348 0.170277 0.607386 0.029 Uiso 1 1 calc R U . . .
C22 C 0.73175(12) 0.4774(4) 0.60759(12) 0.0247(5) Uani 1 1 d . . . . .
H22 H 0.772831 0.458134 0.656161 0.030 Uiso 1 1 calc R U . . .
C23 C 0.72752(12) 0.6753(5) 0.56521(12) 0.0263(5) Uani 1 1 d . . . . .
H23 H 0.765802 0.793055 0.584667 0.032 Uiso 1 1 calc R U . . .
C24 C 0.66717(12) 0.7029(4) 0.49386(12) 0.0217(5) Uani 1 1 d . . . . .
H24 H 0.664690 0.840261 0.465309 0.026 Uiso 1 1 calc R U . . .
O1 O 0.60194(8) 0.2730(3) 0.22651(7) 0.0170(3) Uani 1 1 d . . . . .
H100 H 0.6054(13) 0.132(5) 0.2209(10) 0.026 Uiso 1 1 calc R U . . .
O2 O 0.60230(7) 0.7824(2) 0.22030(7) 0.0146(3) Uani 1 1 d . . . . .
H101 H 0.5920(12) 0.709(3) 0.2544(11) 0.022 Uiso 1 1 calc R U . . .
O3 O 0.56523(8) 0.1888(3) 0.34090(8) 0.0163(3) Uani 1 1 d . . . . .
H102 H 0.5814(11) 0.253(3) 0.3080(13) 0.024 Uiso 1 1 calc R U . . .
O4 O 0.56943(8) 0.6978(3) 0.33910(7) 0.0153(3) Uani 1 1 d . . . . .
H103 H 0.5682(12) 0.843(5) 0.3460(10) 0.023 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
C1 O1 1.429(2) . ?
C1 C2 1.524(3) . ?
C1 C6 1.532(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.530(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.532(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.537(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O2 1.436(2) . ?
C6 C7 1.527(3) . ?
C7 C12 1.391(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O3 1.431(2) . ?
C13 C14 1.522(3) . ?
C13 C18 1.531(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.524(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.522(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.540(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 O4 1.441(2) . ?
C18 C19 1.530(3) . ?
C19 C20 1.391(3) . ?
C19 C24 1.393(3) . ?
C20 C21 1.391(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
O1 H100 0.81(3) . ?
O2 H101 0.89(3) . ?
O3 H102 0.92(3) . ?
O4 H103 0.83(3) . ?

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 C2 111.33(15) . . ?
O1 C1 C6 108.75(15) . . ?
C2 C1 C6 111.35(16) . . ?
O1 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
C6 C1 H1 108.4 . . ?
C1 C2 C3 110.10(16) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 110.85(16) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 111.38(17) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 112.32(15) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
O2 C6 C7 109.89(15) . . ?
O2 C6 C1 109.16(15) . . ?
C7 C6 C1 113.25(16) . . ?
O2 C6 C5 105.96(15) . . ?
C7 C6 C5 109.94(15) . . ?
C1 C6 C5 108.36(15) . . ?
C12 C7 C8 117.84(19) . . ?
C12 C7 C6 122.70(17) . . ?
C8 C7 C6 119.45(18) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O3 C13 C14 111.88(15) . . ?
O3 C13 C18 111.62(15) . . ?
C14 C13 C18 111.47(15) . . ?
O3 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C18 C13 H13 107.2 . . ?
C13 C14 C15 111.22(15) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 111.21(17) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 111.47(17) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 112.21(15) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
O4 C18 C19 109.48(15) . . ?
O4 C18 C13 106.17(14) . . ?
C19 C18 C13 113.08(16) . . ?
O4 C18 C17 110.06(15) . . ?
C19 C18 C17 110.14(15) . . ?
C13 C18 C17 107.83(16) . . ?
C20 C19 C24 117.87(18) . . ?
C20 C19 C18 122.24(18) . . ?
C24 C19 C18 119.83(18) . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 121.1(2) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C1 O1 H100 109.5 . . ?
C6 O2 H101 109.5 . . ?
C13 O3 H102 109.5 . . ?
C18 O4 H103 109.5 . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032

