# 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. 
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#######################################################################

data_10b
_database_code_depnum_ccdc_archive 'CCDC 2401445'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-11-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 Cl2 O'
_chemical_formula_sum            'C9 H8 Cl2 O'
_chemical_formula_weight         203.05
_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 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   31.0324(14)
_cell_length_b                   31.0324(14)
_cell_length_c                   7.7109(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7425.7(8)
_cell_formula_units_Z            32
_cell_measurement_reflns_used    4002
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            66862
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.312
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2190
_reflns_number_total             3271
_reflns_special_details          
;
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0930
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+63.0160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1588
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.93(7)
 0.07(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Others
 Fixed Sof: H1A(0.5) H1AA(0.5) H1B(0.5) H1BA(0.5)
4.a Ternary CH refined with riding coordinates:
 C7A(H7A), C7B(H7B), C9A(H9A), C9B(H9B)
4.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C8B(H8BA,H8BB)
4.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C3B(H3B), C4A(H4A), C4B(H4B), C5A(H5A), C5B(H5B)
4.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1A(H1AA), O1B(H1B), O1B(H1BA)
;
_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
Cl1A Cl 0.86490(5) 0.32548(6) 0.6289(2) 0.0513(5) Uani 1 1 d . . . . .
Cl1B Cl 0.68244(6) 0.35097(6) 0.2085(2) 0.0541(5) Uani 1 1 d . . . . .
Cl2A Cl 0.96417(6) 0.33222(7) 0.7045(2) 0.0589(6) Uani 1 1 d . . . . .
Cl2B Cl 0.66576(6) 0.44715(6) 0.1140(2) 0.0584(6) Uani 1 1 d . . . . .
O1A O 0.77764(15) 0.2742(2) 0.3336(7) 0.0665(16) Uani 1 1 d . . . . .
H1A H 0.763358 0.254959 0.282726 0.100 Uiso 0.5 1 calc R U P A 1
H1AA H 0.779405 0.279666 0.440068 0.100 Uiso 0.5 1 calc R U P B 2
O1B O 0.76034(19) 0.28555(19) 0.6658(7) 0.0695(18) Uani 1 1 d . . . . .
H1B H 0.756594 0.277519 0.562889 0.104 Uiso 0.5 1 calc R U P C 1
H1BA H 0.757628 0.267298 0.745555 0.104 Uiso 0.5 1 calc R U P D 2
C1A C 0.90156(19) 0.32638(19) 0.4583(8) 0.0327(15) Uani 1 1 d . . . . .
C1B C 0.68186(19) 0.3896(2) 0.3716(8) 0.0321(15) Uani 1 1 d . . . . .
C2A C 0.9451(2) 0.3294(2) 0.4941(8) 0.0362(16) Uani 1 1 d . . . . .
C2B C 0.67514(19) 0.4326(2) 0.3282(9) 0.0370(16) Uani 1 1 d . . . . .
C3A C 0.9745(2) 0.3297(2) 0.3589(9) 0.0448(18) Uani 1 1 d . . . . .
H3A H 1.004570 0.330864 0.382453 0.054 Uiso 1 1 calc R U . . .
C3B C 0.6757(2) 0.4639(2) 0.4531(9) 0.0447(18) Uani 1 1 d . . . . .
H3B H 0.671419 0.493223 0.421905 0.054 Uiso 1 1 calc R U . . .
C4A C 0.9599(2) 0.3283(2) 0.1893(9) 0.0428(18) Uani 1 1 d . . . . .
H4A H 0.979891 0.329108 0.095911 0.051 Uiso 1 1 calc R U . . .
C4B C 0.6823(2) 0.4530(2) 0.6232(10) 0.0486(19) Uani 1 1 d . . . . .
H4B H 0.682633 0.474644 0.710404 0.058 Uiso 1 1 calc R U . . .
C5A C 0.9163(2) 0.32582(19) 0.1563(8) 0.0350(16) Uani 1 1 d . . . . .
H5A H 0.906627 0.325211 0.039472 0.042 Uiso 1 1 calc R U . . .
C5B C 0.6887(2) 0.4102(2) 0.6671(8) 0.0401(17) Uani 1 1 d . . . . .
H5B H 0.692960 0.402860 0.785472 0.048 Uiso 1 1 calc R U . . .
C6A C 0.88632(19) 0.32417(18) 0.2884(8) 0.0281(14) Uani 1 1 d . . . . .
C6B C 0.68895(19) 0.3772(2) 0.5428(9) 0.0354(16) Uani 1 1 d . . . . .
C7A C 0.8394(2) 0.3198(2) 0.2531(8) 0.0356(16) Uani 1 1 d . . . . .
H7A H 0.821495 0.343921 0.299618 0.043 Uiso 1 1 calc R U . . .
C7B C 0.6980(2) 0.3321(2) 0.5913(9) 0.0400(17) Uani 1 1 d . . . . .
H7B H 0.692484 0.311191 0.495321 0.048 Uiso 1 1 calc R U . . .
C8A C 0.8223(2) 0.3001(2) 0.0902(10) 0.056(2) Uani 1 1 d . . . . .
H8AA H 0.795963 0.312735 0.038956 0.068 Uiso 1 1 calc R U . . .
H8AB H 0.843392 0.288745 0.005277 0.068 Uiso 1 1 calc R U . . .
C8B C 0.6910(3) 0.3138(3) 0.7652(10) 0.069(3) Uani 1 1 d . . . . .
H8BA H 0.680580 0.333298 0.857643 0.082 Uiso 1 1 calc R U . . .
H8BB H 0.680183 0.283814 0.772694 0.082 Uiso 1 1 calc R U . . .
C9A C 0.8182(2) 0.2773(2) 0.2587(9) 0.0451(18) Uani 1 1 d . . . . .
H9A H 0.837644 0.251964 0.275668 0.054 Uiso 1 1 calc R U . . .
C9B C 0.7345(2) 0.3204(2) 0.6997(10) 0.0450(18) Uani 1 1 d . . . . .
H9B H 0.749930 0.345415 0.752658 0.054 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
Cl1A C1A 1.739(6) . ?
Cl1B C1B 1.738(6) . ?
Cl2A C2A 1.728(6) . ?
Cl2B C2B 1.736(7) . ?
O1A H1A 0.8400 . ?
O1A H1AA 0.8400 . ?
O1A C9A 1.389(7) . ?
O1B H1B 0.8400 . ?
O1B H1BA 0.8400 . ?
O1B C9B 1.370(8) . ?
C1A C2A 1.383(8) . ?
C1A C6A 1.394(8) . ?
C1B C2B 1.392(8) . ?
C1B C6B 1.392(9) . ?
C2A C3A 1.386(9) . ?
C2B C3B 1.368(9) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.385(9) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.371(9) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.380(8) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(9) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.380(8) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.401(9) . ?
C6A C7A 1.487(8) . ?
C6B C7B 1.476(8) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.494(9) . ?
C7A C9A 1.474(9) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.474(10) . ?
C7B C9B 1.454(9) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.484(10) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.456(10) . ?
C9A H9A 1.0000 . ?
C9B H9B 1.0000 . ?

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
C9A O1A H1A 109.5 . . ?
C9A O1A H1AA 109.5 . . ?
C9B O1B H1B 109.5 . . ?
C9B O1B H1BA 109.5 . . ?
C2A C1A Cl1A 119.3(5) . . ?
C2A C1A C6A 121.5(5) . . ?
C6A C1A Cl1A 119.2(5) . . ?
C2B C1B Cl1B 119.3(5) . . ?
C6B C1B Cl1B 119.6(5) . . ?
C6B C1B C2B 121.1(6) . . ?
C1A C2A Cl2A 121.7(5) . . ?
C1A C2A C3A 119.6(6) . . ?
C3A C2A Cl2A 118.7(5) . . ?
C1B C2B Cl2B 120.2(5) . . ?
C3B C2B Cl2B 119.2(5) . . ?
C3B C2B C1B 120.6(6) . . ?
C2A C3A H3A 120.2 . . ?
C4A C3A C2A 119.7(6) . . ?
C4A C3A H3A 120.2 . . ?
C2B C3B H3B 120.0 . . ?
C2B C3B C4B 120.1(6) . . ?
C4B C3B H3B 120.0 . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A C3A 119.8(6) . . ?
C5A C4A H4A 120.1 . . ?
C3B C4B H4B 120.3 . . ?
C3B C4B C5B 119.4(7) . . ?
C5B C4B H4B 120.3 . . ?
C4A C5A H5A 119.1 . . ?
C4A C5A C6A 121.8(6) . . ?
C6A C5A H5A 119.1 . . ?
C4B C5B H5B 118.9 . . ?
C4B C5B C6B 122.2(6) . . ?
C6B C5B H5B 118.9 . . ?
C1A C6A C7A 120.6(5) . . ?
C5A C6A C1A 117.6(5) . . ?
C5A C6A C7A 121.9(6) . . ?
C1B C6B C5B 116.5(6) . . ?
C1B C6B C7B 122.1(6) . . ?
C5B C6B C7B 121.3(6) . . ?
C6A C7A H7A 114.2 . . ?
C6A C7A C8A 122.6(6) . . ?
C8A C7A H7A 114.2 . . ?
C9A C7A C6A 120.9(5) . . ?
C9A C7A H7A 114.2 . . ?
C9A C7A C8A 60.0(5) . . ?
C6B C7B H7B 113.3 . . ?
C8B C7B C6B 124.7(6) . . ?
C8B C7B H7B 113.3 . . ?
C9B C7B C6B 122.2(6) . . ?
C9B C7B H7B 113.3 . . ?
C9B C7B C8B 59.6(5) . . ?
C7A C8A H8AA 117.8 . . ?
C7A C8A H8AB 117.8 . . ?
H8AA C8A H8AB 115.0 . . ?
C9A C8A C7A 59.3(5) . . ?
C9A C8A H8AA 117.8 . . ?
C9A C8A H8AB 117.8 . . ?
C7B C8B H8BA 117.8 . . ?
C7B C8B H8BB 117.8 . . ?
H8BA C8B H8BB 115.0 . . ?
C9B C8B C7B 59.5(5) . . ?
C9B C8B H8BA 117.8 . . ?
C9B C8B H8BB 117.8 . . ?
O1A C9A C7A 118.7(6) . . ?
O1A C9A C8A 118.4(6) . . ?
O1A C9A H9A 115.9 . . ?
C7A C9A C8A 60.7(4) . . ?
C7A C9A H9A 115.9 . . ?
C8A C9A H9A 115.9 . . ?
O1B C9B C7B 122.9(7) . . ?
O1B C9B C8B 119.9(6) . . ?
O1B C9B H9B 114.3 . . ?
C7B C9B C8B 60.8(5) . . ?
C7B C9B H9B 114.3 . . ?
C8B C9B H9B 114.3 . . ?

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
Cl1A C1A C2A Cl2A 0.2(8) . . . . ?
Cl1A C1A C2A C3A 179.4(5) . . . . ?
Cl1A C1A C6A C5A 178.7(5) . . . . ?
Cl1A C1A C6A C7A -1.8(8) . . . . ?
Cl1B C1B C2B Cl2B 2.0(7) . . . . ?
Cl1B C1B C2B C3B -178.2(5) . . . . ?
Cl1B C1B C6B C5B 179.1(5) . . . . ?
Cl1B C1B C6B C7B 1.4(8) . . . . ?
Cl2A C2A C3A C4A -178.8(5) . . . . ?
Cl2B C2B C3B C4B 179.0(5) . . . . ?
C1A C2A C3A C4A 2.0(10) . . . . ?
C1A C6A C7A C8A -154.8(6) . . . . ?
C1A C6A C7A C9A -82.7(8) . . . . ?
C1B C2B C3B C4B -0.8(10) . . . . ?
C1B C6B C7B C8B -157.5(7) . . . . ?
C1B C6B C7B C9B 129.3(7) . . . . ?
C2A C1A C6A C5A -1.0(9) . . . . ?
C2A C1A C6A C7A 178.4(6) . . . . ?
C2A C3A C4A C5A -1.3(11) . . . . ?
C2B C1B C6B C5B 0.4(9) . . . . ?
C2B C1B C6B C7B -177.3(6) . . . . ?
C2B C3B C4B C5B 0.2(10) . . . . ?
C3A C4A C5A C6A -0.7(10) . . . . ?
C3B C4B C5B C6B 0.7(10) . . . . ?
C4A C5A C6A C1A 1.8(9) . . . . ?
C4A C5A C6A C7A -177.6(6) . . . . ?
C4B C5B C6B C1B -1.0(9) . . . . ?
C4B C5B C6B C7B 176.7(6) . . . . ?
C5A C6A C7A C8A 24.6(9) . . . . ?
C5A C6A C7A C9A 96.7(7) . . . . ?
C5B C6B C7B C8B 24.9(10) . . . . ?
C5B C6B C7B C9B -48.2(9) . . . . ?
C6A C1A C2A Cl2A 179.9(5) . . . . ?
C6A C1A C2A C3A -0.9(10) . . . . ?
C6A C7A C8A C9A 109.6(7) . . . . ?
C6A C7A C9A O1A 139.3(7) . . . . ?
C6A C7A C9A C8A -112.3(7) . . . . ?
C6B C1B C2B Cl2B -179.3(5) . . . . ?
C6B C1B C2B C3B 0.5(10) . . . . ?
C6B C7B C8B C9B -110.2(7) . . . . ?
C6B C7B C9B O1B -137.2(7) . . . . ?
C6B C7B C9B C8B 114.3(8) . . . . ?
C7A C8A C9A O1A 108.8(7) . . . . ?
C7B C8B C9B O1B -113.4(8) . . . . ?
C8A C7A C9A O1A -108.4(7) . . . . ?
C8B C7B C9B O1B 108.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.93(7)
2 0.07(7)

