# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_lidan_312_0m1_a
_database_code_depnum_ccdc_archive 'CCDC 2494126'
loop_
_audit_author_name
_audit_author_address
'Bin Zhu'
;Lab of Pharmaceutical Crystal Engineering Research and Technology, School of Pharmacy, East China Un
China
;
_audit_update_record             
;
2025-10-09 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;
_audit_creation_date             2025-09-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Cl O3'
_chemical_formula_sum            'C9 H9 Cl O3'
_chemical_formula_weight         200.61
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 '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                   4.8781(3)
_cell_length_b                   5.6405(3)
_cell_length_c                   16.7996(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.538(2)
_cell_angle_gamma                90
_cell_volume                     460.79(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    748
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      67.841
_cell_measurement_theta_min      10.608
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.239
_exptl_absorpt_coefficient_mu    3.458
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1608 before and 0.0892 after correction.
The Ratio of minimum to maximum transmission is 0.7032.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7841
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.461
_diffrn_reflns_theta_min         2.638
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                1504
_reflns_number_total             1555
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.120(11)
_refine_ls_extinction_coef       0.066(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1555
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.109
_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)+(0.0615P)²+0.0540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3)
2.d Idealised tetrahedral OH refined as rotating group:
 O11(H11), O13(H13)
;
_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
Cl7 Cl 0.0649(2) 0.9746(2) 0.43960(6) 0.0901(5) Uani 1 1 d . . . . .
O11 O 0.2867(5) 0.0274(4) 0.07816(16) 0.0718(7) Uani 1 1 d . . . . .
H11 H 0.402324 -0.041819 0.107722 0.108 Uiso 1 1 calc R U . . .
O13 O 0.5464(4) 0.5034(6) 0.07586(14) 0.0767(8) Uani 1 1 d . . . . .
H13 H 0.607605 0.497818 0.031830 0.115 Uiso 1 1 calc R U . . .
O9 O 0.5209(6) 0.1002(6) 0.21763(17) 0.0838(9) Uani 1 1 d . . . . .
C1 C 0.2634(6) 0.4250(6) 0.25908(19) 0.0542(7) Uani 1 1 d . . . . .
C8 C 0.3399(6) 0.2448(6) 0.20076(19) 0.0565(7) Uani 1 1 d . . . . .
C6 C 0.4178(6) 0.4410(7) 0.3321(2) 0.0667(9) Uani 1 1 d . . . . .
H6 H 0.563680 0.337092 0.343489 0.080 Uiso 1 1 calc R U . . .
C2 C 0.0434(6) 0.5791(6) 0.2439(2) 0.0607(8) Uani 1 1 d . . . . .
H2 H -0.065024 0.567864 0.195935 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2625(5) 0.4509(6) 0.06811(19) 0.0554(7) Uani 1 1 d . . . . .
H12A H 0.204446 0.422474 0.012369 0.066 Uiso 1 1 calc R U . . .
H12B H 0.159996 0.585719 0.085929 0.066 Uiso 1 1 calc R U . . .
C10 C 0.1997(6) 0.2356(5) 0.11667(19) 0.0536(7) Uani 1 1 d . . . . .
H10 H 0.000474 0.226778 0.120289 0.064 Uiso 1 1 calc R U . . .
C5 C 0.3576(7) 0.6090(8) 0.3878(2) 0.0718(10) Uani 1 1 d . . . . .
H5 H 0.461623 0.618376 0.436499 0.086 Uiso 1 1 calc R U . . .
C3 C -0.0163(7) 0.7490(7) 0.2992(2) 0.0661(9) Uani 1 1 d . . . . .
H3 H -0.162042 0.853324 0.288326 0.079 Uiso 1 1 calc R U . . .
C4 C 0.1423(7) 0.7621(7) 0.3705(2) 0.0639(8) 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
Cl7 C4 1.731(4) . ?
O11 H11 0.8200 . ?
O11 C10 1.422(4) . ?
O13 H13 0.8200 . ?
O13 C12 1.412(4) . ?
O9 C8 1.219(4) . ?
C1 C8 1.480(5) . ?
C1 C6 1.390(4) . ?
C1 C2 1.389(4) . ?
C8 C10 1.521(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C10 1.508(5) . ?
C10 H10 0.9800 . ?
C5 H5 0.9300 . ?
C5 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?

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
C10 O11 H11 109.5 . . ?
C12 O13 H13 109.5 . . ?
C6 C1 C8 118.7(3) . . ?
C2 C1 C8 122.7(3) . . ?
C2 C1 C6 118.6(3) . . ?
O9 C8 C1 121.4(3) . . ?
O9 C8 C10 117.2(3) . . ?
C1 C8 C10 121.3(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
O13 C12 H12A 109.4 . . ?
O13 C12 H12B 109.4 . . ?
O13 C12 C10 111.0(2) . . ?
H12A C12 H12B 108.0 . . ?
C10 C12 H12A 109.4 . . ?
C10 C12 H12B 109.4 . . ?
O11 C10 C8 108.8(3) . . ?
O11 C10 C12 109.8(3) . . ?
O11 C10 H10 108.6 . . ?
C8 C10 H10 108.6 . . ?
C12 C10 C8 112.3(3) . . ?
C12 C10 H10 108.6 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.4 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C5 C4 Cl7 119.8(3) . . ?
C5 C4 C3 121.2(4) . . ?
C3 C4 Cl7 119.0(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
O13 C12 C10 O11 -74.7(3) . . . . ?
O13 C12 C10 C8 46.5(4) . . . . ?
O9 C8 C10 O11 9.1(4) . . . . ?
O9 C8 C10 C12 -112.7(4) . . . . ?
C1 C8 C10 O11 -172.1(3) . . . . ?
C1 C8 C10 C12 66.1(4) . . . . ?
C1 C6 C5 C4 -0.1(6) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C8 C1 C6 C5 178.8(3) . . . . ?
C8 C1 C2 C3 -178.2(3) . . . . ?
C6 C1 C8 O9 5.5(5) . . . . ?
C6 C1 C8 C10 -173.3(3) . . . . ?
C6 C1 C2 C3 1.7(5) . . . . ?
C6 C5 C4 Cl7 -179.8(3) . . . . ?
C6 C5 C4 C3 0.9(6) . . . . ?
C2 C1 C8 O9 -174.5(3) . . . . ?
C2 C1 C8 C10 6.7(5) . . . . ?
C2 C1 C6 C5 -1.2(5) . . . . ?
C2 C3 C4 Cl7 -179.7(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
