# 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_d24851
_database_code_depnum_ccdc_archive 'CCDC 2388736'
loop_
_audit_author_name
_audit_author_address
'Lavanya Chandrasekar'
;Fu Jen Catholic University
Taiwan
;
_audit_update_record             
;
2024-10-04 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
5,6-dichloro-2-(tetrahydro-1l4-thiophen-1-ylidene)-1H-indene-1,3(2H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 Cl2 O2 S'
_chemical_formula_sum            'C13 H10 Cl2 O2 S'
_chemical_formula_weight         301.17

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   10.4636(5)
_cell_length_b                   15.3707(7)
_cell_length_c                   8.6501(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.6260(10)
_cell_angle_gamma                90.00
_cell_volume                     1264.68(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5165
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.42

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_correction_T_max  0.9242
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8338
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.43
_reflns_number_total             2274
_reflns_number_gt                2205
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0311P)²+0.4184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_number_reflns         2274
_refine_ls_number_parameters     163
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7325(3) 0.3509(2) 0.9235(3) 0.0485(6) Uani 1 1 d . . .
H1A H 0.6773 0.3981 0.9444 0.058 Uiso 1 1 calc R . .
H1B H 0.7218 0.2975 0.9809 0.058 Uiso 1 1 calc R . .
C2 C 0.8862(3) 0.3765(2) 0.9892(4) 0.0654(10) Uani 1 1 d . . .
H2A H 0.9083 0.4204 1.0805 0.079 Uiso 1 1 calc R . .
H2B H 0.9459 0.3247 1.0382 0.079 Uiso 1 1 calc R . .
C3 C 0.9178(3) 0.4122(3) 0.8522(5) 0.0717(11) Uani 1 1 d . . .
H3A H 1.0198 0.4073 0.8827 0.086 Uiso 1 1 calc R . .
H3B H 0.8919 0.4746 0.8361 0.086 Uiso 1 1 calc R . .
C4 C 0.8387(3) 0.36465(17) 0.6944(3) 0.0399(5) Uani 1 1 d . . .
H4A H 0.8922 0.3128 0.6876 0.048 Uiso 1 1 calc R . .
H4B H 0.8223 0.4023 0.5950 0.048 Uiso 1 1 calc R . .
C5 C 0.5530(2) 0.41317(13) 0.5956(3) 0.0281(4) Uani 1 1 d . . .
C6 C 0.4360(2) 0.39592(14) 0.4356(3) 0.0297(4) Uani 1 1 d . . .
C7 C 0.3675(2) 0.48358(13) 0.3759(2) 0.0255(4) Uani 1 1 d . . .
C8 C 0.2552(2) 0.50553(14) 0.2253(3) 0.0287(4) Uani 1 1 d . . .
H8 H 0.2071 0.4628 0.1420 0.034 Uiso 1 1 calc R . .
C9 C 0.2153(2) 0.59285(14) 0.2005(2) 0.0270(4) Uani 1 1 d . . .
C10 C 0.2839(2) 0.65489(13) 0.3264(2) 0.0260(4) Uani 1 1 d . . .
C11 C 0.3981(2) 0.63188(14) 0.4767(3) 0.0283(4) Uani 1 1 d . . .
H11 H 0.4459 0.6740 0.5616 0.034 Uiso 1 1 calc R . .
C12 C 0.4388(2) 0.54588(13) 0.4974(3) 0.0251(4) Uani 1 1 d . . .
C13 C 0.5626(2) 0.50315(13) 0.6397(2) 0.0268(4) Uani 1 1 d . . .
Cl1 Cl 0.08078(6) 0.62349(4) 0.00989(6) 0.03984(16) Uani 1 1 d . . .
Cl2 Cl 0.22819(6) 0.76203(3) 0.29807(6) 0.03733(15) Uani 1 1 d . . .
O1 O 0.39541(19) 0.32756(10) 0.3567(2) 0.0420(4) Uani 1 1 d . . .
O2 O 0.64931(18) 0.54288(10) 0.76168(19) 0.0384(4) Uani 1 1 d . . .
S1 S 0.67241(5) 0.33201(3) 0.69490(6) 0.03015(14) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0548(16) 0.0579(16) 0.0303(12) 0.0149(11) 0.0153(11) 0.0085(13)
C2 0.0536(19) 0.081(2) 0.0396(15) -0.0164(14) -0.0028(13) 0.0136(16)
C3 0.0414(17) 0.087(2) 0.085(3) -0.043(2) 0.0244(17) -0.0247(17)
C4 0.0330(12) 0.0411(13) 0.0461(13) 0.0024(10) 0.0170(10) 0.0069(10)
C5 0.0277(11) 0.0235(10) 0.0300(10) 0.0024(8) 0.0088(9) -0.0008(9)
C6 0.0266(11) 0.0259(10) 0.0343(11) -0.0019(9) 0.0106(9) -0.0022(9)
C7 0.0210(9) 0.0253(10) 0.0278(10) -0.0023(8) 0.0079(8) -0.0044(8)
C8 0.0222(10) 0.0304(10) 0.0293(10) -0.0048(8) 0.0065(8) -0.0024(8)
C9 0.0184(10) 0.0377(11) 0.0219(9) -0.0006(8) 0.0054(8) 0.0002(8)
C10 0.0277(11) 0.0234(10) 0.0261(10) 0.0003(8) 0.0104(9) 0.0032(8)
C11 0.0289(11) 0.0267(10) 0.0245(10) -0.0037(8) 0.0066(8) -0.0003(8)
C12 0.0255(10) 0.0235(9) 0.0257(9) -0.0011(7) 0.0101(7) -0.0028(8)
C13 0.0277(11) 0.0264(10) 0.0252(10) 0.0002(8) 0.0100(8) 0.0008(8)
Cl1 0.0331(3) 0.0417(3) 0.0296(3) -0.0009(2) -0.0019(2) 0.0055(2)
Cl2 0.0441(3) 0.0268(3) 0.0300(3) 0.0010(2) 0.0044(2) 0.0096(2)
O1 0.0426(10) 0.0240(8) 0.0469(10) -0.0087(7) 0.0063(8) -0.0065(7)
O2 0.0394(9) 0.0275(8) 0.0318(8) -0.0044(6) -0.0016(7) 0.0004(7)
S1 0.0296(3) 0.0208(2) 0.0333(3) 0.00140(19) 0.0064(2) -0.0003(2)

_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
C1 C2 1.517(5) . ?
C1 S1 1.831(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.463(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.463(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 S1 1.813(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C13 1.427(3) . ?
C5 C6 1.439(3) . ?
C5 S1 1.721(2) . ?
C6 O1 1.228(3) . ?
C6 C7 1.512(3) . ?
C7 C8 1.384(3) . ?
C7 C12 1.387(3) . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 Cl1 1.729(2) . ?
C10 C11 1.396(3) . ?
C10 Cl2 1.730(2) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.515(3) . ?
C13 O2 1.229(3) . ?

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
C2 C1 S1 106.20(19) . . ?
C2 C1 H1A 110.5 . . ?
S1 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
S1 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C3 C2 C1 110.8(2) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 109.7(3) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 S1 107.8(2) . . ?
C3 C4 H4A 110.1 . . ?
S1 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
S1 C4 H4B 110.1 . . ?
H4A C4 H4B 108.5 . . ?
C13 C5 C6 111.89(19) . . ?
C13 C5 S1 127.81(17) . . ?
C6 C5 S1 119.74(16) . . ?
O1 C6 C5 130.6(2) . . ?
O1 C6 C7 124.6(2) . . ?
C5 C6 C7 104.85(17) . . ?
C8 C7 C12 121.49(19) . . ?
C8 C7 C6 129.37(19) . . ?
C12 C7 C6 109.11(18) . . ?
C7 C8 C9 117.46(19) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 H8 121.3 . . ?
C8 C9 C10 120.84(19) . . ?
C8 C9 Cl1 118.75(16) . . ?
C10 C9 Cl1 120.40(16) . . ?
C11 C10 C9 120.95(18) . . ?
C11 C10 Cl2 118.69(15) . . ?
C9 C10 Cl2 120.36(16) . . ?
C12 C11 C10 117.54(19) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 C7 121.6(2) . . ?
C11 C12 C13 129.41(19) . . ?
C7 C12 C13 108.91(18) . . ?
O2 C13 C5 131.0(2) . . ?
O2 C13 C12 123.87(18) . . ?
C5 C13 C12 105.15(17) . . ?
C5 S1 C4 107.25(11) . . ?
C5 S1 C1 105.97(12) . . ?
C4 S1 C1 93.47(13) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
