# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_s1223-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2413898'
_audit_update_record             
;
2024-12-31 deposited with the CCDC.	2025-05-14 downloaded from the CCDC.
;
_audit_creation_date             2024-12-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 O2'
_chemical_formula_sum            'C13 H16 O2'
_chemical_formula_weight         204.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9792(10)
_cell_length_b                   6.2593(6)
_cell_length_c                   11.4802(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.827(13)
_cell_angle_gamma                90
_cell_volume                     598.97(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1275
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      63.7070
_cell_measurement_theta_min      5.3140
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2880
_diffrn_reflns_point_group_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_theta_full        66.760
_diffrn_reflns_theta_max         66.760
_diffrn_reflns_theta_min         4.148
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4070
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -63.00   1.00    1.18    --  -42.12-178.00-120.00   25
  2  ω     20.00 116.00   1.00    1.18    --   42.12  37.00 -30.00   96
  3  ω     44.00 107.00   1.00    1.18    --   42.12 178.00 150.00   63
  4  ω     73.00  98.00   1.00    4.71    --   92.50  30.00  60.00   25
  5  ω     91.00 118.00   1.00    4.71    --   92.50 -45.00-150.00   27
  6  ω     56.00 161.00   1.00    4.71    --   92.50  15.00 -30.00  105
  7  ω     30.00  59.00   1.00    4.71    --   92.50 -94.00-180.00   29
  8  ω     80.00 163.00   1.00    4.71    --   92.50  77.00-150.00   83
  9  ω     76.00 117.00   1.00    4.71    --   92.50 125.00 -60.00   41
 10  ω     26.00  51.00   1.00    4.71    --   92.50 -45.00-150.00   25
 11  ω     12.00  38.00   1.00    4.71    --   92.50 -94.00 120.00   26
 12  ω    144.00 169.00   1.00    4.71    --   92.50  77.00-120.00   25
 13  ω     64.00 104.00   1.00    4.71    --   92.50  61.00  30.00   40
 14  ω     34.00  74.00   1.00    4.71    --   92.50 -94.00 -60.00   40
 15  ω     75.00 115.00   1.00    4.71    --   92.50 -45.00  30.00   40
 16  ω     25.00  73.00   1.00    4.71    --   92.50 -45.00  30.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0276380000
_diffrn_orient_matrix_UB_12      0.0076751000
_diffrn_orient_matrix_UB_13      0.1246974000
_diffrn_orient_matrix_UB_21      -0.1281079000
_diffrn_orient_matrix_UB_22      0.1743936000
_diffrn_orient_matrix_UB_23      -0.0540925000
_diffrn_orient_matrix_UB_31      -0.1300892000
_diffrn_orient_matrix_UB_32      -0.1735569000
_diffrn_orient_matrix_UB_33      -0.0493209000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.453
_reflns_Friedel_fraction_full    0.550
_reflns_Friedel_fraction_max     0.550
_reflns_number_gt                1336
_reflns_number_total             1697
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1697
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      0.928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1383
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C3(H3), C9(H9)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.1281(3) 0.8908(5) 0.2369(3) 0.0804(8) Uani 1 1 d . . . . .
H1 H 0.063241 0.806080 0.245488 0.121 Uiso 1 1 calc R U . . .
O2 O 0.9067(3) 0.6361(5) 0.2848(3) 0.0894(9) Uani 1 1 d . . . . .
C4 C 0.5868(3) 0.6298(5) 0.3631(3) 0.0538(8) Uani 1 1 d . . . . .
C5 C 0.4626(4) 0.5206(6) 0.3792(3) 0.0621(8) Uani 1 1 d . . . . .
H5 H 0.482132 0.387497 0.418029 0.074 Uiso 1 1 calc R U . . .
C1 C 0.2771(4) 0.8009(6) 0.2802(3) 0.0600(8) Uani 1 1 d . . . . .
C8 C 0.8063(4) 0.5153(6) 0.2963(3) 0.0622(8) Uani 1 1 d . . . . .
C6 C 0.3083(4) 0.6060(6) 0.3385(3) 0.0635(9) Uani 1 1 d . . . . .
H6 H 0.226264 0.530371 0.350905 0.076 Uiso 1 1 calc R U . . .
C2 C 0.4005(4) 0.9137(6) 0.2651(3) 0.0642(9) Uani 1 1 d . . . . .
H2 H 0.380945 1.047676 0.227394 0.077 Uiso 1 1 calc R U . . .
C7 C 0.7553(4) 0.5389(6) 0.4085(3) 0.0608(9) Uani 1 1 d . . . . .
H7 H 0.752292 0.395912 0.442350 0.073 Uiso 1 1 calc R U . . .
C10 C 0.7680(5) 0.2667(7) 0.1147(3) 0.0759(11) Uani 1 1 d . . . . .
C3 C 0.5530(4) 0.8284(5) 0.3058(3) 0.0634(9) Uani 1 1 d . . . . .
H3 H 0.635033 0.905901 0.294544 0.076 Uiso 1 1 calc R U . . .
C9 C 0.7265(4) 0.3461(6) 0.2073(3) 0.0691(9) Uani 1 1 d . . . . .
H9 H 0.636255 0.286140 0.215601 0.083 Uiso 1 1 calc R U . . .
C13 C 0.8737(5) 0.6744(8) 0.5130(4) 0.0846(12) Uani 1 1 d . . . . .
H13A H 0.876894 0.816393 0.482522 0.127 Uiso 1 1 calc R U . . .
H13B H 0.978586 0.611655 0.539196 0.127 Uiso 1 1 calc R U . . .
H13C H 0.839736 0.680041 0.583037 0.127 Uiso 1 1 calc R U . . .
C12 C 0.9054(6) 0.3427(11) 0.0840(5) 0.112(2) Uani 1 1 d . . . . .
H12A H 0.869809 0.452728 0.021455 0.167 Uiso 1 1 calc R U . . .
H12B H 0.948472 0.225717 0.052417 0.167 Uiso 1 1 calc R U . . .
H12C H 0.986886 0.398826 0.158250 0.167 Uiso 1 1 calc R U . . .
C11 C 0.6767(8) 0.0850(9) 0.0380(4) 0.1136(18) Uani 1 1 d . . . . .
H11A H 0.742117 -0.041250 0.058342 0.170 Uiso 1 1 calc R U . . .
H11B H 0.647683 0.117530 -0.049440 0.170 Uiso 1 1 calc R U . . .
H11C H 0.581427 0.061223 0.055350 0.170 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 H1 0.8200 . ?
O1 C1 1.364(4) . ?
O2 C8 1.221(4) . ?
C4 C5 1.378(4) . ?
C4 C7 1.516(4) . ?
C4 C3 1.386(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(5) . ?
C1 C6 1.370(5) . ?
C1 C2 1.378(5) . ?
C8 C7 1.526(5) . ?
C8 C9 1.461(6) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C7 H7 0.9800 . ?
C7 C13 1.530(5) . ?
C10 C9 1.345(5) . ?
C10 C12 1.482(7) . ?
C10 C11 1.485(7) . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
C5 C4 C7 121.4(3) . . ?
C5 C4 C3 117.6(3) . . ?
C3 C4 C7 120.9(3) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
O1 C1 C6 122.7(3) . . ?
O1 C1 C2 118.0(3) . . ?
C6 C1 C2 119.3(3) . . ?
O2 C8 C7 119.8(3) . . ?
O2 C8 C9 124.2(3) . . ?
C9 C8 C7 116.0(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 H6 119.9 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C4 C7 C8 108.7(2) . . ?
C4 C7 H7 107.9 . . ?
C4 C7 C13 112.0(3) . . ?
C8 C7 H7 107.9 . . ?
C8 C7 C13 112.1(3) . . ?
C13 C7 H7 107.9 . . ?
C9 C10 C12 124.7(4) . . ?
C9 C10 C11 119.9(4) . . ?
C12 C10 C11 115.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C8 C9 H9 116.1 . . ?
C10 C9 C8 127.8(4) . . ?
C10 C9 H9 116.1 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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 C6 C5 179.1(3) . . . . ?
O1 C1 C2 C3 -179.2(3) . . . . ?
O2 C8 C7 C4 108.0(4) . . . . ?
O2 C8 C7 C13 -16.4(5) . . . . ?
O2 C8 C9 C10 13.9(6) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C5 C4 C7 C8 120.5(3) . . . . ?
C5 C4 C7 C13 -115.1(4) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C6 C1 C2 C3 1.5(5) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C7 C4 C5 C6 179.4(3) . . . . ?
C7 C4 C3 C2 -179.5(3) . . . . ?
C7 C8 C9 C10 -167.0(4) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C3 C4 C7 C8 -60.7(4) . . . . ?
C3 C4 C7 C13 63.8(4) . . . . ?
C9 C8 C7 C4 -71.1(4) . . . . ?
C9 C8 C7 C13 164.5(3) . . . . ?
C12 C10 C9 C8 -1.3(7) . . . . ?
C11 C10 C9 C8 176.5(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.779
