# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_shi
_database_code_depnum_ccdc_archive 'CCDC 2502623'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2025-11-13 deposited with the CCDC.	2026-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 Cl O3'
_chemical_formula_sum            'C12 H13 Cl O3'
_chemical_formula_weight         240.67

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'
Cl Cl 0.3639 0.7018 '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                   5.8919(4)
_cell_length_b                   8.2884(4)
_cell_length_c                   23.4295(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.035(6)
_cell_angle_gamma                90
_cell_volume                     1135.55(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    4131
_cell_measurement_theta_min      5.6630
_cell_measurement_theta_max      71.8690

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.902
_shelx_estimated_absorpt_T_min   0.476
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_T_min  0.66650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10064
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.802
_diffrn_reflns_theta_max         73.030
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2227
_reflns_number_gt                1890
_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       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0897P)²+3.7995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2227
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2192
_refine_ls_wR_factor_gt          0.2148
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_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
Cl1 Cl 0.63006(16) 0.24343(12) 0.57046(4) 0.0299(3) Uani 1 1 d . . . . .
C1 C 0.4690(7) 0.2641(5) 0.5031(2) 0.0282(9) Uani 1 1 d . . . . .
C2 C 0.2563(7) 0.3582(5) 0.50072(18) 0.0285(9) Uani 1 1 d . . . . .
O1 O 0.1432(5) 0.3970(4) 0.45559(13) 0.0324(7) Uani 1 1 d . . . . .
O2 O 0.2025(5) 0.3971(4) 0.55168(13) 0.0329(7) Uani 1 1 d . . . . .
H1 H 0.070(10) 0.448(7) 0.550(2) 0.049 Uiso 1 1 d . U . . .
C3 C 0.5503(7) 0.1945(5) 0.45720(19) 0.0287(9) Uani 1 1 d . . . . .
O3 O 0.7543(5) 0.1208(4) 0.46875(13) 0.0315(7) Uani 1 1 d . . . . .
C4 C 0.8526(7) 0.0337(6) 0.42460(19) 0.0333(10) Uani 1 1 d . . . . .
H2 H 0.756883 -0.059960 0.412704 0.050 Uiso 1 1 calc R U . . .
H3 H 1.006678 -0.002719 0.439599 0.050 Uiso 1 1 calc R U . . .
H4 H 0.861224 0.104604 0.391459 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4321(7) 0.1962(5) 0.39696(18) 0.0288(9) Uani 1 1 d . . . . .
H5 H 0.265087 0.204103 0.398208 0.035 Uiso 1 1 calc R U . . .
H6 H 0.462291 0.092736 0.378193 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5070(7) 0.3352(5) 0.36031(19) 0.0305(9) Uani 1 1 d . . . . .
H7 H 0.484720 0.439284 0.379586 0.037 Uiso 1 1 calc R U . . .
H8 H 0.671523 0.323998 0.356254 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3697(7) 0.3338(5) 0.30184(19) 0.0313(9) Uani 1 1 d . . . . .
C8 C 0.4406(8) 0.2473(6) 0.2566(2) 0.0366(10) Uani 1 1 d . . . . .
H9 H 0.582856 0.192034 0.261820 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3066(9) 0.2404(6) 0.2037(2) 0.0424(12) Uani 1 1 d . . . . .
H10 H 0.357485 0.180760 0.173093 0.051 Uiso 1 1 calc R U . . .
C10 C 0.0988(8) 0.3202(7) 0.1955(2) 0.0417(12) Uani 1 1 d . . . . .
H11 H 0.006993 0.315137 0.159226 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0253(8) 0.4072(7) 0.2401(2) 0.0441(12) Uani 1 1 d . . . . .
H12 H -0.116972 0.462512 0.234655 0.053 Uiso 1 1 calc R U . . .
C12 C 0.1605(8) 0.4133(6) 0.2928(2) 0.0362(10) Uani 1 1 d . . . . .
H13 H 0.109237 0.472971 0.323377 0.043 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
Cl1 C1 1.747(5) . ?
C1 C3 1.359(6) . ?
C1 C2 1.472(6) . ?
C2 O1 1.222(5) . ?
C2 O2 1.312(5) . ?
O2 H1 0.89(6) . ?
C3 O3 1.346(5) . ?
C3 C5 1.496(6) . ?
O3 C4 1.440(5) . ?
C4 H2 0.9800 . ?
C4 H3 0.9800 . ?
C4 H4 0.9800 . ?
C5 C6 1.533(6) . ?
C5 H5 0.9900 . ?
C5 H6 0.9900 . ?
C6 C7 1.503(6) . ?
C6 H7 0.9900 . ?
C6 H8 0.9900 . ?
C7 C8 1.387(7) . ?
C7 C12 1.391(6) . ?
C8 C9 1.385(7) . ?
C8 H9 0.9500 . ?
C9 C10 1.384(7) . ?
C9 H10 0.9500 . ?
C10 C11 1.383(8) . ?
C10 H11 0.9500 . ?
C11 C12 1.386(7) . ?
C11 H12 0.9500 . ?
C12 H13 0.9500 . ?

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
C3 C1 C2 125.2(4) . . ?
C3 C1 Cl1 117.9(3) . . ?
C2 C1 Cl1 116.9(3) . . ?
O1 C2 O2 123.8(4) . . ?
O1 C2 C1 123.0(4) . . ?
O2 C2 C1 113.3(4) . . ?
C2 O2 H1 113(4) . . ?
O3 C3 C1 115.2(4) . . ?
O3 C3 C5 119.7(4) . . ?
C1 C3 C5 125.1(4) . . ?
C3 O3 C4 120.7(3) . . ?
O3 C4 H2 109.5 . . ?
O3 C4 H3 109.5 . . ?
H2 C4 H3 109.5 . . ?
O3 C4 H4 109.5 . . ?
H2 C4 H4 109.5 . . ?
H3 C4 H4 109.5 . . ?
C3 C5 C6 113.8(3) . . ?
C3 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
C3 C5 H6 108.8 . . ?
C6 C5 H6 108.8 . . ?
H5 C5 H6 107.7 . . ?
C7 C6 C5 110.2(3) . . ?
C7 C6 H7 109.6 . . ?
C5 C6 H7 109.6 . . ?
C7 C6 H8 109.6 . . ?
C5 C6 H8 109.6 . . ?
H7 C6 H8 108.1 . . ?
C8 C7 C12 118.2(4) . . ?
C8 C7 C6 121.5(4) . . ?
C12 C7 C6 120.2(4) . . ?
C9 C8 C7 120.8(5) . . ?
C9 C8 H9 119.6 . . ?
C7 C8 H9 119.6 . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 H10 119.9 . . ?
C8 C9 H10 119.9 . . ?
C11 C10 C9 119.8(5) . . ?
C11 C10 H11 120.1 . . ?
C9 C10 H11 120.1 . . ?
C10 C11 C12 119.6(5) . . ?
C10 C11 H12 120.2 . . ?
C12 C11 H12 120.2 . . ?
C11 C12 C7 121.4(5) . . ?
C11 C12 H13 119.3 . . ?
C7 C12 H13 119.3 . . ?

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
C3 C1 C2 O1 -7.9(7) . . . . ?
Cl1 C1 C2 O1 171.2(3) . . . . ?
C3 C1 C2 O2 172.8(4) . . . . ?
Cl1 C1 C2 O2 -8.2(5) . . . . ?
C2 C1 C3 O3 176.8(4) . . . . ?
Cl1 C1 C3 O3 -2.3(5) . . . . ?
C2 C1 C3 C5 -2.7(7) . . . . ?
Cl1 C1 C3 C5 178.2(3) . . . . ?
C1 C3 O3 C4 176.1(4) . . . . ?
C5 C3 O3 C4 -4.4(6) . . . . ?
O3 C3 C5 C6 -85.9(5) . . . . ?
C1 C3 C5 C6 93.6(5) . . . . ?
C3 C5 C6 C7 -176.5(4) . . . . ?
C5 C6 C7 C8 -89.6(5) . . . . ?
C5 C6 C7 C12 87.0(5) . . . . ?
C12 C7 C8 C9 0.0(7) . . . . ?
C6 C7 C8 C9 176.7(4) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
C10 C11 C12 C7 0.2(7) . . . . ?
C8 C7 C12 C11 -0.1(7) . . . . ?
C6 C7 C12 C11 -176.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H1 O1 0.89(6) 1.79(6) 2.646(4) 163(6) 3_566 yes
C4 H2 Cl1 0.98 2.81 3.669(5) 146.9 3_656 yes
C5 H5 O1 0.99 2.26 2.851(5) 117.0 . yes

_refine_diff_density_max         0.903
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.105


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
