# 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_22223
_audit_block_doi                 10.5517/ccdc.csd.cc2jxgmk
_database_code_depnum_ccdc_archive 'CCDC 2351059'
loop_
_audit_author_name
_audit_author_address
'bowen liu'
;Changchun University of Technology
China
;
_audit_update_record             
;
2024-04-25 deposited with the CCDC.	2025-02-14 downloaded from the CCDC.
;
_audit_creation_date             2024-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 Cl O'
_chemical_formula_sum            'C22 H19 Cl O'
_chemical_formula_weight         334.82
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8872(5)
_cell_length_b                   10.1609(5)
_cell_length_c                   28.5346(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3446.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5201
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1504 before and 0.0871 after correction.
The Ratio of minimum to maximum transmission is 0.6906.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2103
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25349
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.358
_diffrn_reflns_theta_min         3.097
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2818
_reflns_number_total             3159
_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         0.348
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0975P)²+0.3910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1663
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00X(H00X)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00B,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00G(H00G), C00M(H00M), C00P(H00P), C00R(H00R), C00S(H00S),
 C010(H010), C012(H012), C013(H013), C016(H016), C017(H017), C01B(H01D)
2.d Idealised Me refined as rotating group:
 C019(H01A,H01B,H01C)
;
_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
Cl01 Cl -1.05363(5) 0.18127(7) 0.48108(2) 0.0778(3) Uani 1 1 d . . . . .
O004 O -0.83579(11) 0.09853(14) 0.45235(4) 0.0518(4) Uani 1 1 d . . . . .
C007 C -0.67038(13) -0.07453(15) 0.22797(6) 0.0352(4) Uani 1 1 d . . . . .
C009 C -0.71318(13) 0.05982(15) 0.31296(6) 0.0349(4) Uani 1 1 d . . . . .
C00A C -0.78847(13) -0.03244(16) 0.29553(6) 0.0370(4) Uani 1 1 d . . . . .
H00A H -0.853936 -0.050460 0.312184 0.044 Uiso 1 1 calc R U . . .
C00C C -0.84586(12) 0.17217(14) 0.37114(6) 0.0333(4) Uani 1 1 d . . . . .
C00D C -0.64689(14) -0.14746(16) 0.18380(6) 0.0382(4) Uani 1 1 d . . . . .
C00E C -0.89074(14) 0.15825(15) 0.41615(6) 0.0374(4) Uani 1 1 d . . . . .
C00G C -0.76818(13) -0.09820(16) 0.25388(6) 0.0365(4) Uani 1 1 d . . . . .
H00G H -0.820403 -0.159064 0.242967 0.044 Uiso 1 1 calc R U . . .
C00J C -0.72774(12) 0.12227(16) 0.36080(6) 0.0371(4) Uani 1 1 d . . . . .
H00J H -0.676992 0.198172 0.362267 0.044 Uiso 1 1 calc R U . . .
C00M C -0.61651(13) 0.08489(16) 0.28689(6) 0.0393(4) Uani 1 1 d . . . . .
H00M H -0.565035 0.146931 0.297586 0.047 Uiso 1 1 calc R U . . .
C00P C -0.59580(13) 0.01912(16) 0.24539(6) 0.0404(4) Uani 1 1 d . . . . .
H00P H -0.530521 0.037845 0.228710 0.048 Uiso 1 1 calc R U . . .
C00R C -0.91045(14) 0.23707(16) 0.33755(6) 0.0389(4) Uani 1 1 d . . . . .
H00R H -0.881511 0.247750 0.307508 0.047 Uiso 1 1 calc R U . . .
C00S C -0.67401(16) -0.28035(18) 0.17963(7) 0.0472(4) Uani 1 1 d . . . . .
H00S H -0.707353 -0.324104 0.204659 0.057 Uiso 1 1 calc R U . . .
C00X C -0.71647(15) 0.08098(18) 0.44701(6) 0.0458(4) Uani 1 1 d . . . . .
H00X H -0.679374 0.166630 0.450255 0.055 Uiso 1 1 calc R U . . .
C00Y C -0.69132(15) 0.02634(18) 0.39905(6) 0.0445(4) Uani 1 1 d . . . . .
H00B H -0.730576 -0.056569 0.394988 0.053 Uiso 1 1 calc R U . . .
H00C H -0.611258 0.009553 0.396297 0.053 Uiso 1 1 calc R U . . .
C00Z C -0.99809(16) 0.20564(17) 0.42550(7) 0.0443(4) Uani 1 1 d . . . . .
C010 C -1.01611(15) 0.28595(17) 0.34756(7) 0.0447(4) Uani 1 1 d . . . . .
H010 H -1.057050 0.329828 0.324598 0.054 Uiso 1 1 calc R U . . .
C012 C -1.06085(14) 0.26927(18) 0.39203(7) 0.0466(4) Uani 1 1 d . . . . .
H012 H -1.132339 0.300705 0.399095 0.056 Uiso 1 1 calc R U . . .
C013 C -0.59620(18) -0.0854(2) 0.14595(7) 0.0538(5) Uani 1 1 d . . . . .
H013 H -0.576068 0.002786 0.148366 0.065 Uiso 1 1 calc R U . . .
C016 C -0.65169(17) -0.3478(2) 0.13849(9) 0.0603(6) Uani 1 1 d . . . . .
H016 H -0.670279 -0.436412 0.136066 0.072 Uiso 1 1 calc R U . . .
C017 C -0.6021(2) -0.2844(3) 0.10114(8) 0.0655(6) Uani 1 1 d . . . . .
H017 H -0.586905 -0.330229 0.073652 0.079 Uiso 1 1 calc R U . . .
C019 C -0.6794(2) -0.0070(3) 0.48673(8) 0.0650(6) Uani 1 1 d . . . . .
H01A H -0.703245 0.030307 0.516005 0.098 Uiso 1 1 calc R U . . .
H01B H -0.598960 -0.014812 0.486462 0.098 Uiso 1 1 calc R U . . .
H01C H -0.712571 -0.092553 0.483002 0.098 Uiso 1 1 calc R U . . .
C01B C -0.5751(2) -0.1526(3) 0.10462(8) 0.0680(6) Uani 1 1 d . . . . .
H01D H -0.542782 -0.109122 0.079299 0.082 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
Cl01 C00Z 1.7357(19) . ?
O004 C00E 1.365(2) . ?
O004 C00X 1.438(2) . ?
C007 C00D 1.489(2) . ?
C007 C00G 1.399(2) . ?
C007 C00P 1.392(2) . ?
C009 C00A 1.388(2) . ?
C009 C00J 1.515(2) . ?
C009 C00M 1.392(2) . ?
C00A H00A 0.9300 . ?
C00A C00G 1.385(2) . ?
C00C C00E 1.398(2) . ?
C00C C00J 1.522(2) . ?
C00C C00R 1.394(2) . ?
C00D C00S 1.393(2) . ?
C00D C013 1.388(3) . ?
C00E C00Z 1.390(3) . ?
C00G H00G 0.9300 . ?
C00J H00J 0.9800 . ?
C00J C00Y 1.526(2) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.382(2) . ?
C00P H00P 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C010 1.381(2) . ?
C00S H00S 0.9300 . ?
C00S C016 1.385(3) . ?
C00X H00X 0.9800 . ?
C00X C00Y 1.507(2) . ?
C00X C019 1.510(3) . ?
C00Y H00B 0.9700 . ?
C00Y H00C 0.9700 . ?
C00Z C012 1.374(3) . ?
C010 H010 0.9300 . ?
C010 C012 1.386(3) . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C01B 1.386(3) . ?
C016 H016 0.9300 . ?
C016 C017 1.378(4) . ?
C017 H017 0.9300 . ?
C017 C01B 1.380(3) . ?
C019 H01A 0.9600 . ?
C019 H01B 0.9600 . ?
C019 H01C 0.9600 . ?
C01B H01D 0.9300 . ?

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
C00E O004 C00X 116.56(14) . . ?
C00G C007 C00D 121.20(14) . . ?
C00P C007 C00D 121.54(14) . . ?
C00P C007 C00G 117.26(15) . . ?
C00A C009 C00J 122.14(14) . . ?
C00A C009 C00M 117.65(15) . . ?
C00M C009 C00J 119.93(14) . . ?
C009 C00A H00A 119.3 . . ?
C00G C00A C009 121.41(15) . . ?
C00G C00A H00A 119.3 . . ?
C00E C00C C00J 119.77(14) . . ?
C00R C00C C00E 117.99(15) . . ?
C00R C00C C00J 122.18(15) . . ?
C00S C00D C007 120.76(16) . . ?
C013 C00D C007 120.93(15) . . ?
C013 C00D C00S 118.31(17) . . ?
O004 C00E C00C 123.90(15) . . ?
O004 C00E C00Z 116.62(15) . . ?
C00Z C00E C00C 119.47(15) . . ?
C007 C00G H00G 119.5 . . ?
C00A C00G C007 121.04(15) . . ?
C00A C00G H00G 119.5 . . ?
C009 C00J C00C 114.80(13) . . ?
C009 C00J H00J 107.3 . . ?
C009 C00J C00Y 110.14(13) . . ?
C00C C00J H00J 107.3 . . ?
C00C C00J C00Y 109.64(13) . . ?
C00Y C00J H00J 107.3 . . ?
C009 C00M H00M 119.5 . . ?
C00P C00M C009 121.09(15) . . ?
C00P C00M H00M 119.5 . . ?
C007 C00P H00P 119.2 . . ?
C00M C00P C007 121.54(15) . . ?
C00M C00P H00P 119.2 . . ?
C00C C00R H00R 119.0 . . ?
C010 C00R C00C 121.94(16) . . ?
C010 C00R H00R 119.0 . . ?
C00D C00S H00S 119.8 . . ?
C016 C00S C00D 120.50(19) . . ?
C016 C00S H00S 119.8 . . ?
O004 C00X H00X 108.9 . . ?
O004 C00X C00Y 109.75(14) . . ?
O004 C00X C019 106.35(16) . . ?
C00Y C00X H00X 108.9 . . ?
C00Y C00X C019 113.95(16) . . ?
C019 C00X H00X 108.9 . . ?
C00J C00Y H00B 109.4 . . ?
C00J C00Y H00C 109.4 . . ?
C00X C00Y C00J 110.96(14) . . ?
C00X C00Y H00B 109.4 . . ?
C00X C00Y H00C 109.4 . . ?
H00B C00Y H00C 108.0 . . ?
C00E C00Z Cl01 118.39(14) . . ?
C012 C00Z Cl01 119.73(14) . . ?
C012 C00Z C00E 121.88(17) . . ?
C00R C010 H010 120.2 . . ?
C00R C010 C012 119.63(17) . . ?
C012 C010 H010 120.2 . . ?
C00Z C012 C010 119.06(16) . . ?
C00Z C012 H012 120.5 . . ?
C010 C012 H012 120.5 . . ?
C00D C013 H013 119.4 . . ?
C01B C013 C00D 121.11(19) . . ?
C01B C013 H013 119.4 . . ?
C00S C016 H016 119.8 . . ?
C017 C016 C00S 120.43(19) . . ?
C017 C016 H016 119.8 . . ?
C016 C017 H017 120.1 . . ?
C016 C017 C01B 119.82(19) . . ?
C01B C017 H017 120.1 . . ?
C00X C019 H01A 109.5 . . ?
C00X C019 H01B 109.5 . . ?
C00X C019 H01C 109.5 . . ?
H01A C019 H01B 109.5 . . ?
H01A C019 H01C 109.5 . . ?
H01B C019 H01C 109.5 . . ?
C013 C01B H01D 120.1 . . ?
C017 C01B C013 119.8(2) . . ?
C017 C01B H01D 120.1 . . ?

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
Cl01 C00Z C012 C010 -178.88(15) . . . . ?
O004 C00E C00Z Cl01 -1.7(2) . . . . ?
O004 C00E C00Z C012 179.02(16) . . . . ?
O004 C00X C00Y C00J 62.6(2) . . . . ?
C007 C00D C00S C016 -179.83(17) . . . . ?
C007 C00D C013 C01B -179.43(19) . . . . ?
C009 C00A C00G C007 0.4(2) . . . . ?
C009 C00J C00Y C00X -174.04(14) . . . . ?
C009 C00M C00P C007 0.0(3) . . . . ?
C00A C009 C00J C00C -47.1(2) . . . . ?
C00A C009 C00J C00Y 77.26(19) . . . . ?
C00A C009 C00M C00P -0.7(2) . . . . ?
C00C C00E C00Z Cl01 177.56(13) . . . . ?
C00C C00E C00Z C012 -1.7(3) . . . . ?
C00C C00J C00Y C00X -46.79(19) . . . . ?
C00C C00R C010 C012 -0.8(3) . . . . ?
C00D C007 C00G C00A 178.45(15) . . . . ?
C00D C007 C00P C00M -178.66(15) . . . . ?
C00D C00S C016 C017 0.1(3) . . . . ?
C00D C013 C01B C017 -1.6(4) . . . . ?
C00E O004 C00X C00Y -46.5(2) . . . . ?
C00E O004 C00X C019 -170.17(16) . . . . ?
C00E C00C C00J C009 141.96(15) . . . . ?
C00E C00C C00J C00Y 17.4(2) . . . . ?
C00E C00C C00R C010 -0.5(2) . . . . ?
C00E C00Z C012 C010 0.4(3) . . . . ?
C00G C007 C00D C00S -38.1(2) . . . . ?
C00G C007 C00D C013 142.74(18) . . . . ?
C00G C007 C00P C00M 0.9(2) . . . . ?
C00J C009 C00A C00G -173.49(14) . . . . ?
C00J C009 C00M C00P 173.41(15) . . . . ?
C00J C00C C00E O004 -1.7(2) . . . . ?
C00J C00C C00E C00Z 179.14(15) . . . . ?
C00J C00C C00R C010 -177.83(14) . . . . ?
C00M C009 C00A C00G 0.5(2) . . . . ?
C00M C009 C00J C00C 139.12(15) . . . . ?
C00M C009 C00J C00Y -96.56(17) . . . . ?
C00P C007 C00D C00S 141.43(17) . . . . ?
C00P C007 C00D C013 -37.8(2) . . . . ?
C00P C007 C00G C00A -1.1(2) . . . . ?
C00R C00C C00E O004 -179.07(15) . . . . ?
C00R C00C C00E C00Z 1.8(2) . . . . ?
C00R C00C C00J C009 -40.8(2) . . . . ?
C00R C00C C00J C00Y -165.35(14) . . . . ?
C00R C010 C012 C00Z 0.9(3) . . . . ?
C00S C00D C013 C01B 1.4(3) . . . . ?
C00S C016 C017 C01B -0.4(4) . . . . ?
C00X O004 C00E C00C 16.7(2) . . . . ?
C00X O004 C00E C00Z -164.05(16) . . . . ?
C013 C00D C00S C016 -0.6(3) . . . . ?
C016 C017 C01B C013 1.1(4) . . . . ?
C019 C00X C00Y C00J -178.26(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
