# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_TTM-BT
_database_code_depnum_ccdc_archive 'CCDC 2513981'
loop_
_audit_author_name
_audit_author_address
'Alina Sonina'
;Vorozhtsov Novosibirsk Institute of Organic Chemistry of SB RAS
Russia
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2025-09-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
'(4-[Benzo[b]thiophen-2-yl]-2,6-dichloro-phenyl)bis(2,4,6-trichlorophenyl)methyl radical'
_chemical_formula_moiety         'C27 H11 Cl8 S'
_chemical_formula_sum            'C27 H11 Cl8 S'
_chemical_formula_weight         651.02
_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'
S S 0.1246 0.1234 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.414(4)
_cell_length_b                   12.147(3)
_cell_length_c                   15.983(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.618(11)
_cell_angle_gamma                90
_cell_volume                     2730.8(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1704
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.06
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0559 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.8691.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1300
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.1113
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17210
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.104
_diffrn_ambient_temperature      296.15
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2057
_reflns_number_total             4819
_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_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         4819
_refine_ls_number_restraints     312
_refine_ls_R_factor_all          0.1685
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      0.994
_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)+(0.0501P)²+0.4485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1342
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C21-C22 = C21A-C22A
 1.44 with sigma of 0.01
 C27-C26 = C27A-C26A = C22-C27 = C22A-C27A = C22-C23 = C22A-C23A
 1.4 with sigma of 0.01
 C20-S1 = S1-C27 = C20-S1A = S1A-C27A
 1.74 with sigma of 0.01
 C20-C21 = C20-C21A
 1.37 with sigma of 0.01
 C23-C24 = C23A-C24A = C24-C25 = C24A-C25A = C25-C26 = C25A-C26A
 1.38 with sigma of 0.01
 S1-C20 \\sim S1A-C20
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C22-C27 \\sim C22A-C27A
 with sigma of 0.02
 S1-C27 \\sim S1A-C27A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 S1-C22 \\sim S1A-C22A
 with sigma of 0.04
 C21-C20 \\sim C21A-C20
 with sigma of 0.02
 C20-C22 \\sim C20-C22A
 with sigma of 0.04
 C22-C26 \\sim C22A-C26A
 with sigma of 0.04
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
 C27-C26 \\sim C27A-C26A
 with sigma of 0.02
 C26-C25 \\sim C26A-C25A
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C25-C24 \\sim C25A-C24A
 with sigma of 0.02
 S1-C26 \\sim S1A-C26A
 with sigma of 0.04
 C21-C27 \\sim C21A-C27A
 with sigma of 0.04
 C21-C23 \\sim C21A-C23A
 with sigma of 0.04
 C20-C27 \\sim C20-C27A
 with sigma of 0.04
 C27-C23 \\sim C27A-C23A
 with sigma of 0.04
 C27-C25 \\sim C27A-C25A
 with sigma of 0.04
 C26-C24 \\sim C26A-C24A
 with sigma of 0.04
 C23-C25 \\sim C23A-C25A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
S1 \\sim S1A \\sim C20 \\sim C21 \\sim C21A \\sim C22 \\sim C22A \\sim C23
\\sim C23A \\sim C24 \\sim C24A \\sim C25 \\sim C25A \\sim C26 \\sim C26A \\sim
C27 \\sim C27A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
4. Others
 Sof(S1A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=1-FVAR(1)
 Sof(S1)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=
 Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(C27)=FVAR(1)
 Fixed X: C22A(0.939755)
 Fixed Y: C22A(0.70234)
 Fixed Z: C22A(0.96522)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C12(H12), C16(H16), C18(H18), C21(H21), C21A(H21A),
 C23(H23), C23A(H23A), C24(H24), C24A(H24A), C25(H25), C25A(H25A), C26(H26),
 C26A(H26A)
;
_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
Cl1 Cl 0.89175(15) -0.18432(17) 0.70138(14) 0.1319(8) Uani 1 1 d . . . . .
Cl2 Cl 0.72978(11) 0.12680(13) 0.48557(8) 0.0814(5) Uani 1 1 d . . . . .
Cl3 Cl 0.71318(15) 0.13971(15) 0.82220(9) 0.1155(7) Uani 1 1 d . . . . .
Cl4 Cl 0.34547(15) 0.27819(18) 0.33923(13) 0.1399(8) Uani 1 1 d . . . . .
Cl5 Cl 0.51353(11) 0.06748(12) 0.62280(10) 0.0876(5) Uani 1 1 d . . . . .
Cl6 Cl 0.66811(12) 0.44010(13) 0.52256(9) 0.0882(5) Uani 1 1 d . . . . .
Cl7 Cl 0.53539(11) 0.37467(13) 0.72126(10) 0.0863(5) Uani 1 1 d . . . . .
Cl8 Cl 0.88758(11) 0.29082(14) 0.66239(10) 0.1002(6) Uani 1 1 d . . . . .
S1 S 0.9510(2) 0.5988(3) 0.9103(3) 0.0648(11) Uani 0.602(5) 1 d D U P A 1
S1A S 0.7609(5) 0.7047(6) 0.8885(6) 0.0769(17) Uani 0.398(5) 1 d D U P A 2
C1 C 0.6736(4) 0.2381(5) 0.6409(3) 0.0583(14) Uani 1 1 d . . . . .
C2 C 0.7230(4) 0.1324(4) 0.6544(3) 0.0550(14) Uani 1 1 d . . . . .
C3 C 0.7517(4) 0.0746(5) 0.5883(3) 0.0569(14) Uani 1 1 d . . . . .
C4 C 0.8028(4) -0.0216(5) 0.6017(4) 0.0692(16) Uani 1 1 d . . . . .
H4 H 0.820353 -0.057647 0.556176 0.083 Uiso 1 1 calc R U . . .
C5 C 0.8276(4) -0.0638(5) 0.6833(5) 0.0778(17) Uani 1 1 d . . . . .
C6 C 0.8002(5) -0.0130(6) 0.7499(4) 0.0829(19) Uani 1 1 d . . . . .
H6 H 0.815046 -0.043587 0.804534 0.099 Uiso 1 1 calc R U . . .
C7 C 0.7507(4) 0.0837(5) 0.7354(3) 0.0722(17) Uani 1 1 d . . . . .
C8 C 0.5914(4) 0.2515(4) 0.5700(3) 0.0523(13) Uani 1 1 d . . . . .
C9 C 0.5165(4) 0.1756(4) 0.5528(3) 0.0605(15) Uani 1 1 d . . . . .
C10 C 0.4411(4) 0.1840(5) 0.4838(4) 0.0773(17) Uani 1 1 d . . . . .
H10 H 0.392338 0.132279 0.475422 0.093 Uiso 1 1 calc R U . . .
C11 C 0.4385(5) 0.2691(6) 0.4276(4) 0.0792(18) Uani 1 1 d . . . . .
C12 C 0.5077(5) 0.3488(5) 0.4421(3) 0.0720(17) Uani 1 1 d . . . . .
H12 H 0.504616 0.408187 0.404906 0.086 Uiso 1 1 calc R U . . .
C13 C 0.5804(4) 0.3397(4) 0.5113(3) 0.0582(15) Uani 1 1 d . . . . .
C14 C 0.7135(4) 0.3306(4) 0.6955(3) 0.0526(14) Uani 1 1 d . . . . .
C15 C 0.8095(4) 0.3577(4) 0.7142(3) 0.0604(15) Uani 1 1 d . . . . .
C16 C 0.8490(4) 0.4417(4) 0.7679(3) 0.0577(14) Uani 1 1 d . . . . .
H16 H 0.914189 0.454414 0.778813 0.069 Uiso 1 1 calc R U . . .
C17 C 0.7904(4) 0.5082(4) 0.8062(3) 0.0497(13) Uani 1 1 d . . . . .
C18 C 0.6944(4) 0.4847(4) 0.7872(3) 0.0569(14) Uani 1 1 d . . . . .
H18 H 0.653863 0.528157 0.811225 0.068 Uiso 1 1 calc R U . . .
C19 C 0.6569(3) 0.4004(4) 0.7346(3) 0.0530(14) Uani 1 1 d . . . . .
C20 C 0.8303(3) 0.5968(4) 0.8645(3) 0.0530(12) Uani 1 1 d D U . . .
C21 C 0.7809(9) 0.6797(12) 0.8912(13) 0.068(3) Uani 0.602(5) 1 d D U P A 1
H21 H 0.715253 0.687524 0.875258 0.082 Uiso 0.602(5) 1 calc R U P A 1
C21A C 0.9213(9) 0.6068(15) 0.9109(15) 0.061(3) Uani 0.398(5) 1 d D U P A 2
H21A H 0.968255 0.555456 0.907571 0.074 Uiso 0.398(5) 1 calc R U P A 2
C22 C 0.8431(7) 0.7541(12) 0.9474(12) 0.0635(18) Uani 0.602(5) 1 d D U P A 1
C22A C 0.939755 0.702340 0.965220 0.061(2) Uani 0.398(5) 1 d D U P A 2
C23 C 0.8193(8) 0.8521(9) 0.9832(7) 0.081(2) Uani 0.602(5) 1 d D U P A 1
H23 H 0.756905 0.877344 0.971192 0.098 Uiso 0.602(5) 1 calc R U P A 1
C23A C 1.0222(9) 0.7385(12) 1.0210(11) 0.071(3) Uani 0.398(5) 1 d D U P A 2
H23A H 1.078336 0.698789 1.026253 0.085 Uiso 0.398(5) 1 calc R U P A 2
C24 C 0.8905(8) 0.9106(9) 1.0368(8) 0.088(3) Uani 0.602(5) 1 d D U P A 1
H24 H 0.875670 0.976923 1.059907 0.106 Uiso 0.602(5) 1 calc R U P A 1
C24A C 1.0209(11) 0.8334(12) 1.0687(11) 0.078(3) Uani 0.398(5) 1 d D U P A 2
H24A H 1.076287 0.857652 1.105458 0.093 Uiso 0.398(5) 1 calc R U P A 2
C25 C 0.9830(8) 0.8731(9) 1.0568(8) 0.080(2) Uani 0.602(5) 1 d D U P A 1
H25 H 1.028563 0.911932 1.095890 0.096 Uiso 0.602(5) 1 calc R U P A 1
C25A C 0.9373(11) 0.8922(14) 1.0616(12) 0.082(3) Uani 0.398(5) 1 d D U P A 2
H25A H 0.937585 0.955892 1.093930 0.099 Uiso 0.398(5) 1 calc R U P A 2
C26 C 1.0091(7) 0.7785(8) 1.0196(8) 0.071(2) Uani 0.602(5) 1 d D U P A 1
H26 H 1.072191 0.755923 1.029906 0.085 Uiso 0.602(5) 1 calc R U P A 1
C26A C 0.8535(12) 0.8588(14) 1.0079(12) 0.078(3) Uani 0.398(5) 1 d D U P A 2
H26A H 0.797227 0.897701 1.004596 0.094 Uiso 0.398(5) 1 calc R U P A 2
C27 C 0.9376(6) 0.7180(6) 0.9663(5) 0.0585(17) Uani 0.602(5) 1 d D U P A 1
C27A C 0.8565(8) 0.7639(19) 0.9588(18) 0.066(2) Uani 0.398(5) 1 d D U P A 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
Cl1 C5 1.722(6) . ?
Cl2 C3 1.724(5) . ?
Cl3 C7 1.734(5) . ?
Cl4 C11 1.726(6) . ?
Cl5 C9 1.732(5) . ?
Cl6 C13 1.737(5) . ?
Cl7 C19 1.746(5) . ?
Cl8 C15 1.737(5) . ?
S1 C20 1.734(5) . ?
S1 C27 1.735(6) . ?
S1A C20 1.741(6) . ?
S1A C27A 1.733(8) . ?
C1 C2 1.461(7) . ?
C1 C8 1.459(7) . ?
C1 C14 1.461(7) . ?
C2 C3 1.403(6) . ?
C2 C7 1.400(7) . ?
C3 C4 1.372(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(7) . ?
C5 C6 1.360(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(7) . ?
C8 C9 1.400(7) . ?
C8 C13 1.410(6) . ?
C9 C10 1.373(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.364(7) . ?
C11 C12 1.373(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.351(7) . ?
C14 C15 1.390(6) . ?
C14 C19 1.414(6) . ?
C15 C16 1.375(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.402(6) . ?
C17 C18 1.380(6) . ?
C17 C20 1.457(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.360(6) . ?
C20 C21 1.354(8) . ?
C20 C21A 1.365(9) . ?
C21 H21 0.9300 . ?
C21 C22 1.441(8) . ?
C21A H21A 0.9300 . ?
C21A C22A 1.439(9) . ?
C22 C23 1.395(7) . ?
C22 C27 1.399(7) . ?
C22A C23A 1.392(8) . ?
C22A C27A 1.398(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(8) . ?
C23A H23A 0.9300 . ?
C23A C24A 1.384(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(8) . ?
C24A H24A 0.9300 . ?
C24A C25A 1.384(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(8) . ?
C25A H25A 0.9300 . ?
C25A C26A 1.381(9) . ?
C26 H26 0.9300 . ?
C26 C27 1.394(7) . ?
C26A H26A 0.9300 . ?
C26A C27A 1.401(8) . ?

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
C20 S1 C27 90.9(3) . . ?
C27A S1A C20 92.4(5) . . ?
C2 C1 C14 118.1(5) . . ?
C8 C1 C2 120.0(5) . . ?
C8 C1 C14 121.7(5) . . ?
C3 C2 C1 122.9(5) . . ?
C7 C2 C1 122.6(4) . . ?
C7 C2 C3 114.4(5) . . ?
C2 C3 Cl2 120.6(5) . . ?
C4 C3 Cl2 116.2(4) . . ?
C4 C3 C2 123.1(5) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.9(5) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 Cl1 119.6(5) . . ?
C6 C5 Cl1 119.4(6) . . ?
C6 C5 C4 120.9(6) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.1(5) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 Cl3 119.9(5) . . ?
C6 C7 Cl3 116.3(5) . . ?
C6 C7 C2 123.5(5) . . ?
C9 C8 C1 122.7(5) . . ?
C9 C8 C13 113.6(5) . . ?
C13 C8 C1 123.7(5) . . ?
C8 C9 Cl5 119.9(5) . . ?
C10 C9 Cl5 116.7(5) . . ?
C10 C9 C8 123.3(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(6) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 Cl4 119.5(5) . . ?
C10 C11 C12 120.6(6) . . ?
C12 C11 Cl4 119.9(5) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(5) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 Cl6 119.4(4) . . ?
C12 C13 Cl6 116.3(4) . . ?
C12 C13 C8 124.1(5) . . ?
C15 C14 C1 123.7(4) . . ?
C15 C14 C19 114.0(4) . . ?
C19 C14 C1 122.4(5) . . ?
C14 C15 Cl8 120.3(4) . . ?
C16 C15 Cl8 114.9(4) . . ?
C16 C15 C14 124.6(4) . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.5(5) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C20 120.8(5) . . ?
C18 C17 C16 117.2(5) . . ?
C18 C17 C20 122.0(4) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.4(5) . . ?
C19 C18 H18 118.8 . . ?
C14 C19 Cl7 119.9(4) . . ?
C18 C19 Cl7 117.6(4) . . ?
C18 C19 C14 122.4(5) . . ?
C17 C20 S1 120.0(4) . . ?
C17 C20 S1A 122.1(4) . . ?
C21 C20 S1 113.8(7) . . ?
C21 C20 C17 126.1(7) . . ?
C21A C20 S1A 110.1(6) . . ?
C21A C20 C17 127.7(6) . . ?
C20 C21 H21 124.3 . . ?
C20 C21 C22 111.4(10) . . ?
C22 C21 H21 124.3 . . ?
C20 C21A H21A 122.3 . . ?
C20 C21A C22A 115.4(9) . . ?
C22A C21A H21A 122.3 . . ?
C23 C22 C21 128.0(8) . . ?
C23 C22 C27 119.6(9) . . ?
C27 C22 C21 112.5(8) . . ?
C23A C22A C21A 131.3(7) . . ?
C23A C22A C27A 118.5(8) . . ?
C27A C22A C21A 110.2(6) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 C22 118.5(10) . . ?
C24 C23 H23 120.7 . . ?
C22A C23A H23A 119.9 . . ?
C24A C23A C22A 120.2(12) . . ?
C24A C23A H23A 119.9 . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.5(10) . . ?
C25 C24 H24 119.2 . . ?
C23A C24A H24A 120.0 . . ?
C23A C24A C25A 120.1(14) . . ?
C25A C24A H24A 120.0 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.0(10) . . ?
C26 C25 H25 119.5 . . ?
C24A C25A H25A 119.1 . . ?
C26A C25A C24A 121.8(14) . . ?
C26A C25A H25A 119.1 . . ?
C25 C26 H26 121.1 . . ?
C25 C26 C27 117.8(9) . . ?
C27 C26 H26 121.1 . . ?
C25A C26A H26A 121.3 . . ?
C25A C26A C27A 117.4(12) . . ?
C27A C26A H26A 121.3 . . ?
C22 C27 S1 111.2(6) . . ?
C26 C27 S1 127.2(7) . . ?
C26 C27 C22 121.4(8) . . ?
C22A C27A S1A 112.0(7) . . ?
C22A C27A C26A 122.0(10) . . ?
C26A C27A S1A 126.0(8) . . ?

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
Cl1 C5 C6 C7 178.9(5) . . . . ?
Cl2 C3 C4 C5 176.1(4) . . . . ?
Cl4 C11 C12 C13 -179.4(4) . . . . ?
Cl5 C9 C10 C11 178.4(4) . . . . ?
Cl8 C15 C16 C17 173.6(4) . . . . ?
S1 C20 C21 C22 4(2) . . . . ?
S1A C20 C21A C22A -2(2) . . . . ?
C1 C2 C3 Cl2 0.1(7) . . . . ?
C1 C2 C3 C4 176.2(5) . . . . ?
C1 C2 C7 Cl3 8.4(7) . . . . ?
C1 C2 C7 C6 -177.3(5) . . . . ?
C1 C8 C9 Cl5 6.2(6) . . . . ?
C1 C8 C9 C10 -176.5(5) . . . . ?
C1 C8 C13 Cl6 -0.4(6) . . . . ?
C1 C8 C13 C12 175.3(5) . . . . ?
C1 C14 C15 Cl8 7.6(7) . . . . ?
C1 C14 C15 C16 -177.5(5) . . . . ?
C1 C14 C19 Cl7 2.2(6) . . . . ?
C1 C14 C19 C18 178.3(4) . . . . ?
C2 C1 C8 C9 47.9(6) . . . . ?
C2 C1 C8 C13 -130.6(5) . . . . ?
C2 C1 C14 C15 45.4(6) . . . . ?
C2 C1 C14 C19 -134.2(5) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C2 C7 Cl3 -175.3(4) . . . . ?
C3 C2 C7 C6 -1.1(8) . . . . ?
C3 C4 C5 Cl1 -179.9(4) . . . . ?
C3 C4 C5 C6 1.6(9) . . . . ?
C4 C5 C6 C7 -2.6(9) . . . . ?
C5 C6 C7 Cl3 176.8(5) . . . . ?
C5 C6 C7 C2 2.4(10) . . . . ?
C7 C2 C3 Cl2 -176.2(4) . . . . ?
C7 C2 C3 C4 -0.1(8) . . . . ?
C8 C1 C2 C3 49.1(7) . . . . ?
C8 C1 C2 C7 -134.9(5) . . . . ?
C8 C1 C14 C15 -129.6(5) . . . . ?
C8 C1 C14 C19 50.8(6) . . . . ?
C8 C9 C10 C11 1.1(8) . . . . ?
C9 C8 C13 Cl6 -179.0(3) . . . . ?
C9 C8 C13 C12 -3.3(7) . . . . ?
C9 C10 C11 Cl4 178.3(5) . . . . ?
C9 C10 C11 C12 -3.4(9) . . . . ?
C10 C11 C12 C13 2.3(9) . . . . ?
C11 C12 C13 Cl6 177.0(4) . . . . ?
C11 C12 C13 C8 1.2(8) . . . . ?
C13 C8 C9 Cl5 -175.2(3) . . . . ?
C13 C8 C9 C10 2.1(7) . . . . ?
C14 C1 C2 C3 -126.0(5) . . . . ?
C14 C1 C2 C7 49.9(7) . . . . ?
C14 C1 C8 C9 -137.2(5) . . . . ?
C14 C1 C8 C13 44.3(6) . . . . ?
C14 C15 C16 C17 -1.5(7) . . . . ?
C15 C14 C19 Cl7 -177.4(4) . . . . ?
C15 C14 C19 C18 -1.4(7) . . . . ?
C15 C16 C17 C18 0.0(7) . . . . ?
C15 C16 C17 C20 179.0(4) . . . . ?
C16 C17 C18 C19 0.7(7) . . . . ?
C16 C17 C20 S1 -17.6(6) . . . . ?
C16 C17 C20 S1A 160.8(6) . . . . ?
C16 C17 C20 C21 165.5(13) . . . . ?
C16 C17 C20 C21A -23.0(17) . . . . ?
C17 C18 C19 Cl7 176.1(4) . . . . ?
C17 C18 C19 C14 0.0(7) . . . . ?
C17 C20 C21 C22 -178.9(13) . . . . ?
C17 C20 C21A C22A -178.3(10) . . . . ?
C18 C17 C20 S1 161.4(4) . . . . ?
C18 C17 C20 S1A -20.1(7) . . . . ?
C18 C17 C20 C21 -15.5(14) . . . . ?
C18 C17 C20 C21A 156.0(17) . . . . ?
C19 C14 C15 Cl8 -172.7(4) . . . . ?
C19 C14 C15 C16 2.2(7) . . . . ?
C20 S1 C27 C22 -1.3(12) . . . . ?
C20 S1 C27 C26 -177.2(9) . . . . ?
C20 S1A C27A C22A -1(2) . . . . ?
C20 S1A C27A C26A -178(3) . . . . ?
C20 C17 C18 C19 -178.3(4) . . . . ?
C20 C21 C22 C23 175.7(18) . . . . ?
C20 C21 C22 C27 -5(3) . . . . ?
C20 C21A C22A C23A 179.5(15) . . . . ?
C20 C21A C22A C27A 1(3) . . . . ?
C21 C22 C23 C24 179(2) . . . . ?
C21 C22 C27 S1 4(2) . . . . ?
C21 C22 C27 C26 180.0(16) . . . . ?
C21A C22A C23A C24A -178.2(19) . . . . ?
C21A C22A C27A S1A 0(3) . . . . ?
C21A C22A C27A C26A 177(3) . . . . ?
C22 C23 C24 C25 -1.5(19) . . . . ?
C22A C23A C24A C25A 1(3) . . . . ?
C23 C22 C27 S1 -176.9(14) . . . . ?
C23 C22 C27 C26 -1(2) . . . . ?
C23 C24 C25 C26 4.0(18) . . . . ?
C23A C22A C27A S1A -178.5(16) . . . . ?
C23A C22A C27A C26A -1(4) . . . . ?
C23A C24A C25A C26A 0(3) . . . . ?
C24 C25 C26 C27 -4.6(18) . . . . ?
C24A C25A C26A C27A -2(3) . . . . ?
C25 C26 C27 S1 178.6(9) . . . . ?
C25 C26 C27 C22 3.0(19) . . . . ?
C25A C26A C27A S1A 179(2) . . . . ?
C25A C26A C27A C22A 2(4) . . . . ?
C27 S1 C20 C17 -178.9(4) . . . . ?
C27 S1 C20 C21 -1.6(12) . . . . ?
C27 C22 C23 C24 0(2) . . . . ?
C27A S1A C20 C17 178.3(13) . . . . ?
C27A S1A C20 C21A 2(2) . . . . ?
C27A C22A C23A C24A 0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/water'
####################################################################### 
# 
# 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_TTM-DBT
_database_code_depnum_ccdc_archive 'CCDC 2513983'
loop_
_audit_author_name
_audit_author_address
'Alina Sonina'
;Vorozhtsov Novosibirsk Institute of Organic Chemistry of SB RAS
Russia
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_TTM-DBT             
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        35% Check
RESPONSE: Alert occurs due to poor crystal quality. Unfortunately, it was not possible to grow better crystals.
;
_vrf_PLAT340_TTM-DBT             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01051 Ang.
RESPONSE: Alert occurs due to poor crystal quality. Unfortunately, it was not possible to grow better crystals.
;
# Added during the CSD deposition process: Monday 08 December 2025 04:04 AM
# end Validation Reply Form

_audit_creation_date             2024-10-18
_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        
'(4-[Dibenzo[b,d]thiophen-2-yl]-2,6-dichloro-phenyl)bis(2,4,6-trichlorophenyl)methyl radical'
_chemical_formula_moiety         'C31 H13 Cl8 S'
_chemical_formula_sum            'C31 H13 Cl8 S'
_chemical_formula_weight         701.07
_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'
S S 0.1246 0.1234 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.8323(17)
_cell_length_b                   19.2071(18)
_cell_length_c                   10.2458(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.385(5)
_cell_angle_gamma                90
_cell_volume                     2900.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1047
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.94
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.756
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8856.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1543
_diffrn_reflns_av_unetI/netI     0.2177
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19114
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.130
_diffrn_ambient_temperature      296.15
_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             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1776
_reflns_number_total             5112
_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_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2441
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      0.943
_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)+(0.0460P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1550
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C12(H12), C16(H16), C18(H18), C21(H21), C22(H22),
 C25(H25), C28(H28), C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.05691(19) 0.24948(9) 0.4311(3) 0.1240(10) Uani 1 1 d . . . . .
Cl2 Cl 0.21972(17) 0.40990(11) 0.1070(2) 0.1097(9) Uani 1 1 d . . . . .
Cl3 Cl 0.11639(13) 0.51434(8) 0.56153(19) 0.0723(6) Uani 1 1 d . . . . .
Cl4 Cl 0.12042(19) 0.65156(11) -0.2336(2) 0.1198(10) Uani 1 1 d . . . . .
Cl5 Cl 0.00603(15) 0.54749(10) 0.1977(2) 0.0875(7) Uani 1 1 d . . . . .
Cl6 Cl 0.36676(15) 0.57510(9) 0.1571(2) 0.0908(7) Uani 1 1 d . . . . .
Cl7 Cl 0.15492(16) 0.68092(10) 0.3711(2) 0.1091(9) Uani 1 1 d . . . . .
Cl8 Cl 0.37273(14) 0.45370(8) 0.4456(2) 0.0843(7) Uani 1 1 d . . . . .
S1 S 0.61650(16) 0.77573(9) 1.0496(2) 0.0867(8) Uani 1 1 d . . . . .
C1 C 0.2078(6) 0.5299(4) 0.3038(8) 0.094(3) Uani 1 1 d . . . . .
C2 C 0.1691(5) 0.4613(3) 0.3349(7) 0.0544(19) Uani 1 1 d . . . . .
C3 C 0.1705(5) 0.4042(4) 0.2515(7) 0.064(2) Uani 1 1 d . . . . .
C4 C 0.1368(5) 0.3395(4) 0.2792(8) 0.069(2) Uani 1 1 d . . . . .
H4 H 0.139176 0.302608 0.220864 0.082 Uiso 1 1 calc R U . . .
C5 C 0.0997(5) 0.3310(3) 0.3951(9) 0.067(2) Uani 1 1 d . . . . .
C6 C 0.0939(5) 0.3841(3) 0.4797(7) 0.057(2) Uani 1 1 d . . . . .
H6 H 0.067007 0.377961 0.556605 0.069 Uiso 1 1 calc R U . . .
C7 C 0.1292(4) 0.4483(3) 0.4489(7) 0.0497(19) Uani 1 1 d . . . . .
C8 C 0.1852(7) 0.5621(3) 0.1743(7) 0.059(2) Uani 1 1 d . . . . .
C9 C 0.0960(6) 0.5706(3) 0.1138(8) 0.065(2) Uani 1 1 d . . . . .
C10 C 0.0771(6) 0.5988(4) -0.0068(9) 0.074(2) Uani 1 1 d . . . . .
H10 H 0.016920 0.604286 -0.041916 0.089 Uiso 1 1 calc R U . . .
C11 C 0.1454(9) 0.6195(3) -0.0782(8) 0.075(3) Uani 1 1 d . . . . .
C12 C 0.2323(7) 0.6145(3) -0.0233(9) 0.074(3) Uani 1 1 d . . . . .
H12 H 0.279016 0.630585 -0.068862 0.089 Uiso 1 1 calc R U . . .
C13 C 0.2520(5) 0.5861(3) 0.0987(9) 0.061(2) Uani 1 1 d . . . . .
C14 C 0.2644(5) 0.5683(3) 0.4088(7) 0.058(2) Uani 1 1 d . . . . .
C15 C 0.3389(5) 0.5381(3) 0.4844(8) 0.058(2) Uani 1 1 d . . . . .
C16 C 0.3915(5) 0.5714(3) 0.5850(7) 0.062(2) Uani 1 1 d . . . . .
H16 H 0.440928 0.548470 0.629569 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3711(5) 0.6387(3) 0.6198(7) 0.0534(19) Uani 1 1 d . . . . .
C18 C 0.2975(5) 0.6697(3) 0.5466(7) 0.065(2) Uani 1 1 d . . . . .
H18 H 0.281488 0.714841 0.567298 0.078 Uiso 1 1 calc R U . . .
C19 C 0.2485(5) 0.6367(4) 0.4467(7) 0.067(2) Uani 1 1 d . . . . .
C20 C 0.4263(4) 0.6737(3) 0.7321(6) 0.0510(18) Uani 1 1 d . . . . .
C21 C 0.4308(5) 0.7467(3) 0.7350(7) 0.070(2) Uani 1 1 d . . . . .
H21 H 0.394988 0.772055 0.671512 0.083 Uiso 1 1 calc R U . . .
C22 C 0.4867(5) 0.7819(3) 0.8292(8) 0.073(2) Uani 1 1 d . . . . .
H22 H 0.490228 0.830205 0.828811 0.087 Uiso 1 1 calc R U . . .
C23 C 0.5374(5) 0.7429(3) 0.9247(7) 0.065(2) Uani 1 1 d . . . . .
C24 C 0.5320(5) 0.6707(3) 0.9260(7) 0.0542(19) Uani 1 1 d . . . . .
C25 C 0.4766(5) 0.6368(3) 0.8288(7) 0.058(2) Uani 1 1 d . . . . .
H25 H 0.473389 0.588477 0.829010 0.070 Uiso 1 1 calc R U . . .
C26 C 0.5916(5) 0.6414(3) 1.0361(7) 0.060(2) Uani 1 1 d . . . . .
C27 C 0.6400(5) 0.6929(3) 1.1080(7) 0.064(2) Uani 1 1 d . . . . .
C28 C 0.7012(5) 0.6751(4) 1.2181(8) 0.080(2) Uani 1 1 d . . . . .
H28 H 0.733189 0.709396 1.267624 0.096 Uiso 1 1 calc R U . . .
C29 C 0.7125(5) 0.6073(5) 1.2503(8) 0.084(3) Uani 1 1 d . . . . .
H29 H 0.751913 0.594997 1.323701 0.101 Uiso 1 1 calc R U . . .
C30 C 0.6661(6) 0.5554(4) 1.1754(9) 0.087(3) Uani 1 1 d . . . . .
H30 H 0.677037 0.509013 1.197575 0.105 Uiso 1 1 calc R U . . .
C31 C 0.6036(4) 0.5717(3) 1.0677(7) 0.0546(19) Uani 1 1 d . . . . .
H31 H 0.571298 0.537169 1.019115 0.065 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 C5 1.745(7) . ?
Cl2 C3 1.726(7) . ?
Cl3 C7 1.740(6) . ?
Cl4 C11 1.709(8) . ?
Cl5 C9 1.724(8) . ?
Cl6 C13 1.753(7) . ?
Cl7 C19 1.735(7) . ?
Cl8 C15 1.755(6) . ?
S1 C23 1.754(7) . ?
S1 C27 1.721(7) . ?
C1 C2 1.486(9) . ?
C1 C8 1.468(10) . ?
C1 C14 1.484(9) . ?
C2 C3 1.392(9) . ?
C2 C7 1.389(9) . ?
C3 C4 1.380(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(10) . ?
C5 C6 1.347(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(8) . ?
C8 C9 1.406(9) . ?
C8 C13 1.402(9) . ?
C9 C10 1.350(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(10) . ?
C11 C12 1.352(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(9) . ?
C14 C15 1.402(8) . ?
C14 C19 1.397(8) . ?
C15 C16 1.379(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(8) . ?
C17 C18 1.387(8) . ?
C17 C20 1.496(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.347(8) . ?
C20 C21 1.404(8) . ?
C20 C25 1.369(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(8) . ?
C23 C24 1.390(8) . ?
C24 C25 1.382(8) . ?
C24 C26 1.466(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(8) . ?
C26 C31 1.384(8) . ?
C27 C28 1.409(9) . ?
C28 H28 0.9300 . ?
C28 C29 1.349(9) . ?
C29 H29 0.9300 . ?
C29 C30 1.391(9) . ?
C30 H30 0.9300 . ?
C30 C31 1.396(9) . ?
C31 H31 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
C27 S1 C23 90.8(3) . . ?
C8 C1 C2 120.8(6) . . ?
C8 C1 C14 120.0(6) . . ?
C14 C1 C2 119.0(6) . . ?
C3 C2 C1 122.3(7) . . ?
C7 C2 C1 123.4(7) . . ?
C7 C2 C3 114.2(6) . . ?
C2 C3 Cl2 120.9(6) . . ?
C4 C3 Cl2 115.5(6) . . ?
C4 C3 C2 123.6(7) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(7) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 Cl1 118.6(6) . . ?
C6 C5 Cl1 119.5(7) . . ?
C6 C5 C4 121.8(7) . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.2(7) . . ?
C7 C6 H6 120.9 . . ?
C2 C7 Cl3 121.0(5) . . ?
C2 C7 C6 123.8(6) . . ?
C6 C7 Cl3 115.1(6) . . ?
C9 C8 C1 123.8(8) . . ?
C13 C8 C1 122.2(8) . . ?
C13 C8 C9 114.0(7) . . ?
C8 C9 Cl5 119.5(7) . . ?
C10 C9 Cl5 117.7(8) . . ?
C10 C9 C8 122.7(8) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.9(8) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 Cl4 120.3(9) . . ?
C12 C11 Cl4 120.7(9) . . ?
C12 C11 C10 119.0(8) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(9) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 Cl6 119.4(7) . . ?
C12 C13 Cl6 117.5(8) . . ?
C12 C13 C8 123.0(7) . . ?
C15 C14 C1 122.8(6) . . ?
C19 C14 C1 124.7(7) . . ?
C19 C14 C15 112.5(6) . . ?
C14 C15 Cl8 119.0(5) . . ?
C16 C15 Cl8 116.4(6) . . ?
C16 C15 C14 124.5(6) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(6) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 116.3(6) . . ?
C16 C17 C20 120.1(6) . . ?
C18 C17 C20 123.7(6) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 C17 122.3(6) . . ?
C19 C18 H18 118.8 . . ?
C14 C19 Cl7 119.2(6) . . ?
C18 C19 Cl7 116.5(5) . . ?
C18 C19 C14 124.1(6) . . ?
C21 C20 C17 119.0(6) . . ?
C25 C20 C17 122.2(6) . . ?
C25 C20 C21 118.7(6) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.8(6) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 H22 121.1 . . ?
C21 C22 C23 117.9(6) . . ?
C23 C22 H22 121.1 . . ?
C22 C23 S1 126.0(5) . . ?
C22 C23 C24 121.2(6) . . ?
C24 C23 S1 112.7(5) . . ?
C23 C24 C26 111.1(6) . . ?
C25 C24 C23 119.5(6) . . ?
C25 C24 C26 129.3(6) . . ?
C20 C25 C24 120.7(6) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C24 111.6(6) . . ?
C31 C26 C24 127.0(6) . . ?
C31 C26 C27 121.4(6) . . ?
C26 C27 S1 113.7(5) . . ?
C26 C27 C28 120.1(6) . . ?
C28 C27 S1 126.2(6) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 C27 118.9(7) . . ?
C29 C28 H28 120.6 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.0(7) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 119.3 . . ?
C29 C30 C31 121.3(7) . . ?
C31 C30 H30 119.3 . . ?
C26 C31 C30 117.3(6) . . ?
C26 C31 H31 121.4 . . ?
C30 C31 H31 121.4 . . ?

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
Cl1 C5 C6 C7 179.5(5) . . . . ?
Cl2 C3 C4 C5 177.7(6) . . . . ?
Cl4 C11 C12 C13 -177.2(5) . . . . ?
Cl5 C9 C10 C11 178.9(5) . . . . ?
Cl8 C15 C16 C17 178.3(5) . . . . ?
S1 C23 C24 C25 -176.2(6) . . . . ?
S1 C23 C24 C26 2.5(8) . . . . ?
S1 C27 C28 C29 -179.4(7) . . . . ?
C1 C2 C3 Cl2 1.2(10) . . . . ?
C1 C2 C3 C4 178.6(7) . . . . ?
C1 C2 C7 Cl3 3.4(10) . . . . ?
C1 C2 C7 C6 -179.1(6) . . . . ?
C1 C8 C9 Cl5 4.1(9) . . . . ?
C1 C8 C9 C10 -178.3(6) . . . . ?
C1 C8 C13 Cl6 2.2(9) . . . . ?
C1 C8 C13 C12 178.3(6) . . . . ?
C1 C14 C15 Cl8 5.1(10) . . . . ?
C1 C14 C15 C16 -178.2(7) . . . . ?
C1 C14 C19 Cl7 1.9(11) . . . . ?
C1 C14 C19 C18 176.5(8) . . . . ?
C2 C1 C8 C9 50.5(11) . . . . ?
C2 C1 C8 C13 -128.4(8) . . . . ?
C2 C1 C14 C15 52.4(11) . . . . ?
C2 C1 C14 C19 -125.5(8) . . . . ?
C2 C3 C4 C5 0.2(11) . . . . ?
C3 C2 C7 Cl3 -177.0(5) . . . . ?
C3 C2 C7 C6 0.5(10) . . . . ?
C3 C4 C5 Cl1 180.0(5) . . . . ?
C3 C4 C5 C6 1.4(12) . . . . ?
C4 C5 C6 C7 -1.9(11) . . . . ?
C5 C6 C7 Cl3 178.5(5) . . . . ?
C5 C6 C7 C2 0.9(10) . . . . ?
C7 C2 C3 Cl2 -178.5(5) . . . . ?
C7 C2 C3 C4 -1.1(10) . . . . ?
C8 C1 C2 C3 48.6(12) . . . . ?
C8 C1 C2 C7 -131.7(8) . . . . ?
C8 C1 C14 C15 -132.2(9) . . . . ?
C8 C1 C14 C19 50.0(12) . . . . ?
C8 C9 C10 C11 1.3(11) . . . . ?
C9 C8 C13 Cl6 -176.8(4) . . . . ?
C9 C8 C13 C12 -0.7(9) . . . . ?
C9 C10 C11 Cl4 177.1(5) . . . . ?
C9 C10 C11 C12 -3.4(11) . . . . ?
C10 C11 C12 C13 3.3(11) . . . . ?
C11 C12 C13 Cl6 174.9(5) . . . . ?
C11 C12 C13 C8 -1.3(10) . . . . ?
C13 C8 C9 Cl5 -176.9(4) . . . . ?
C13 C8 C9 C10 0.7(9) . . . . ?
C14 C1 C2 C3 -136.0(8) . . . . ?
C14 C1 C2 C7 43.7(11) . . . . ?
C14 C1 C8 C9 -124.8(8) . . . . ?
C14 C1 C8 C13 56.3(11) . . . . ?
C14 C15 C16 C17 1.6(11) . . . . ?
C15 C14 C19 Cl7 -176.1(5) . . . . ?
C15 C14 C19 C18 -1.6(11) . . . . ?
C15 C16 C17 C18 -1.3(10) . . . . ?
C15 C16 C17 C20 177.8(6) . . . . ?
C16 C17 C18 C19 -0.3(11) . . . . ?
C16 C17 C20 C21 154.8(7) . . . . ?
C16 C17 C20 C25 -21.7(10) . . . . ?
C17 C18 C19 Cl7 176.6(6) . . . . ?
C17 C18 C19 C14 1.9(12) . . . . ?
C17 C20 C21 C22 -174.2(7) . . . . ?
C17 C20 C25 C24 175.3(6) . . . . ?
C18 C17 C20 C21 -26.2(11) . . . . ?
C18 C17 C20 C25 157.3(7) . . . . ?
C19 C14 C15 Cl8 -176.8(5) . . . . ?
C19 C14 C15 C16 -0.1(11) . . . . ?
C20 C17 C18 C19 -179.4(7) . . . . ?
C20 C21 C22 C23 -1.7(12) . . . . ?
C21 C20 C25 C24 -1.2(11) . . . . ?
C21 C22 C23 S1 177.0(6) . . . . ?
C21 C22 C23 C24 -0.3(12) . . . . ?
C22 C23 C24 C25 1.5(12) . . . . ?
C22 C23 C24 C26 -179.9(7) . . . . ?
C23 S1 C27 C26 0.9(6) . . . . ?
C23 S1 C27 C28 -178.8(7) . . . . ?
C23 C24 C25 C20 -0.7(11) . . . . ?
C23 C24 C26 C27 -1.8(9) . . . . ?
C23 C24 C26 C31 -179.9(7) . . . . ?
C24 C26 C27 S1 0.4(8) . . . . ?
C24 C26 C27 C28 -180.0(7) . . . . ?
C24 C26 C31 C30 178.2(7) . . . . ?
C25 C20 C21 C22 2.4(12) . . . . ?
C25 C24 C26 C27 176.7(7) . . . . ?
C25 C24 C26 C31 -1.4(13) . . . . ?
C26 C24 C25 C20 -179.1(7) . . . . ?
C26 C27 C28 C29 1.0(12) . . . . ?
C27 S1 C23 C22 -179.5(8) . . . . ?
C27 S1 C23 C24 -1.9(6) . . . . ?
C27 C26 C31 C30 0.3(11) . . . . ?
C27 C28 C29 C30 1.2(13) . . . . ?
C28 C29 C30 C31 -2.7(13) . . . . ?
C29 C30 C31 C26 1.9(12) . . . . ?
C31 C26 C27 S1 178.6(6) . . . . ?
C31 C26 C27 C28 -1.7(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/water'
####################################################################### 
# 
# 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_TTM-TP
_database_code_depnum_ccdc_archive 'CCDC 2513982'
loop_
_audit_author_name
_audit_author_address
'Alina Sonina'
;Vorozhtsov Novosibirsk Institute of Organic Chemistry of SB RAS
Russia
;
_audit_update_record             
;
2025-12-08 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_TTM-TP              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01278 Ang.
RESPONSE: Alert occurs due to poor crystal quality. Unfortunately, it was not possible to grow better crystals.
;
# Added during the CSD deposition process: Monday 08 December 2025 04:04 AM
# end Validation Reply Form

_audit_creation_date             2024-12-18
_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        
'(4-[5-Phenylthiophene-2-yl]-2,6-dichloro-phenyl)bis(2,4,6-trichlorophenyl)methyl radical'
_chemical_formula_moiety         'C29 H13 Cl8 S'
_chemical_formula_sum            'C29 H13 Cl8 S'
_chemical_formula_weight         677.05
_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'
S S 0.1246 0.1234 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.594(5)
_cell_length_b                   18.111(5)
_cell_length_c                   10.613(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.466(15)
_cell_angle_gamma                90
_cell_volume                     2792.3(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    298.61
_cell_measurement_theta_max      20.29
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1278 before and 0.0936 after correction.
The Ratio of minimum to maximum transmission is 0.6397.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       elongated
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1240
_diffrn_reflns_av_unetI/netI     0.1672
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17720
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.022
_diffrn_ambient_temperature      298.61
_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             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2319
_reflns_number_total             4927
_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_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1866
_refine_ls_R_factor_gt           0.0850
_refine_ls_restrained_S_all      1.036
_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)+(0.0628P)²+5.6518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2391
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C25(H25), C26(H26), C27(H27), C6(H6), C18(H18), C21(H21),
 C22(H22), C28(H28), C29(H29), C10(H10), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl4 Cl 0.8560(2) 0.63741(14) 1.2175(2) 0.0853(9) Uani 1 1 d . . . . .
Cl1 Cl 0.9798(3) 0.23702(15) 0.5960(3) 0.1115(12) Uani 1 1 d . . . . .
Cl3 Cl 0.87980(16) 0.50426(13) 0.4402(2) 0.0656(7) Uani 1 1 d . . . . .
Cl7 Cl 0.8241(2) 0.68357(13) 0.6297(2) 0.0819(8) Uani 1 1 d . . . . .
Cl8 Cl 0.63309(16) 0.42810(12) 0.5539(2) 0.0642(7) Uani 1 1 d . . . . .
Cl6 Cl 0.62005(16) 0.57684(14) 0.8189(2) 0.0695(7) Uani 1 1 d . . . . .
Cl5 Cl 0.98831(15) 0.54420(13) 0.7948(2) 0.0637(7) Uani 1 1 d . . . . .
Cl2 Cl 0.7844(2) 0.39741(13) 0.8911(2) 0.0789(8) Uani 1 1 d . . . . .
S1 S 0.50390(18) 0.59968(13) 0.1601(2) 0.0622(7) Uani 1 1 d . . . . .
C11 C 0.8362(7) 0.6099(4) 1.0608(7) 0.055(2) Uani 1 1 d . . . . .
C12 C 0.7484(7) 0.6067(4) 1.0042(7) 0.056(2) Uani 1 1 d . . . . .
H12 H 0.699212 0.620725 1.048395 0.067 Uiso 1 1 calc R U . . .
C13 C 0.7333(6) 0.5826(4) 0.8804(8) 0.053(2) Uani 1 1 d . . . . .
C8 C 0.8050(6) 0.5564(4) 0.8141(7) 0.0440(19) Uani 1 1 d . . . . .
C1 C 0.7876(5) 0.5207(4) 0.6889(7) 0.045(2) Uani 1 1 d . . . . .
C14 C 0.7286(6) 0.5555(4) 0.5865(7) 0.0449(19) Uani 1 1 d . . . . .
C15 C 0.6610(6) 0.5165(4) 0.5139(8) 0.049(2) Uani 1 1 d . . . . .
C16 C 0.6103(6) 0.5470(4) 0.4083(7) 0.050(2) Uani 1 1 d . . . . .
H16 H 0.565490 0.518898 0.362244 0.060 Uiso 1 1 calc R U . . .
C17 C 0.6266(5) 0.6196(4) 0.3712(7) 0.0430(19) Uani 1 1 d . . . . .
C20 C 0.5777(6) 0.6515(4) 0.2552(8) 0.052(2) Uani 1 1 d . . . . .
C23 C 0.4797(6) 0.6719(5) 0.0549(8) 0.057(2) Uani 1 1 d . . . . .
C24 C 0.4132(6) 0.6622(5) -0.0546(8) 0.060(2) Uani 1 1 d . . . . .
C25 C 0.3874(8) 0.7231(6) -0.1315(11) 0.091(3) Uani 1 1 d . . . . .
H25 H 0.413202 0.769214 -0.112407 0.109 Uiso 1 1 calc R U . . .
C26 C 0.3233(9) 0.7148(9) -0.2361(13) 0.108(4) Uani 1 1 d . . . . .
H26 H 0.306822 0.755173 -0.287427 0.130 Uiso 1 1 calc R U . . .
C27 C 0.2851(9) 0.6481(9) -0.2632(10) 0.101(4) Uani 1 1 d . . . . .
H27 H 0.240650 0.643616 -0.331623 0.121 Uiso 1 1 calc R U . . .
C5 C 0.9228(7) 0.3176(5) 0.6217(9) 0.064(2) Uani 1 1 d . . . . .
C6 C 0.9194(6) 0.3723(5) 0.5337(8) 0.056(2) Uani 1 1 d . . . . .
H6 H 0.946633 0.365094 0.458935 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8769(5) 0.4374(4) 0.5537(7) 0.048(2) Uani 1 1 d . . . . .
C2 C 0.8334(5) 0.4507(4) 0.6664(7) 0.0386(18) Uani 1 1 d . . . . .
C18 C 0.6926(6) 0.6605(4) 0.4464(8) 0.053(2) Uani 1 1 d . . . . .
H18 H 0.703985 0.709251 0.425469 0.063 Uiso 1 1 calc R U . . .
C19 C 0.7404(6) 0.6294(5) 0.5503(8) 0.053(2) Uani 1 1 d . . . . .
C21 C 0.5854(7) 0.7210(5) 0.2116(9) 0.069(3) Uani 1 1 d . . . . .
H21 H 0.623343 0.757077 0.251112 0.083 Uiso 1 1 calc R U . . .
C22 C 0.5291(8) 0.7316(6) 0.1001(10) 0.080(3) Uani 1 1 d . . . . .
H22 H 0.525426 0.776878 0.058671 0.097 Uiso 1 1 calc R U . . .
C28 C 0.3098(9) 0.5880(7) -0.1934(11) 0.097(4) Uani 1 1 d . . . . .
H28 H 0.284544 0.542088 -0.215669 0.116 Uiso 1 1 calc R U . . .
C29 C 0.3733(7) 0.5951(6) -0.0878(9) 0.074(3) Uani 1 1 d . . . . .
H29 H 0.389191 0.553707 -0.038505 0.089 Uiso 1 1 calc R U . . .
C10 C 0.9102(6) 0.5895(4) 0.9963(8) 0.055(2) Uani 1 1 d . . . . .
H10 H 0.970197 0.593103 1.034000 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8921(6) 0.5638(4) 0.8744(7) 0.049(2) Uani 1 1 d . . . . .
C3 C 0.8386(6) 0.3924(5) 0.7530(7) 0.052(2) Uani 1 1 d . . . . .
C4 C 0.8823(6) 0.3274(5) 0.7326(9) 0.064(3) Uani 1 1 d . . . . .
H4 H 0.884756 0.290128 0.793069 0.077 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
Cl4 C11 1.734(8) . ?
Cl1 C5 1.715(9) . ?
Cl3 C7 1.712(8) . ?
Cl7 C19 1.723(9) . ?
Cl8 C15 1.715(8) . ?
Cl6 C13 1.721(9) . ?
Cl5 C9 1.743(8) . ?
Cl2 C3 1.733(8) . ?
S1 C20 1.689(9) . ?
S1 C23 1.734(9) . ?
C11 C12 1.363(12) . ?
C11 C10 1.383(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(11) . ?
C13 C8 1.399(10) . ?
C8 C1 1.478(10) . ?
C8 C9 1.373(11) . ?
C1 C14 1.463(10) . ?
C1 C2 1.463(10) . ?
C14 C15 1.386(11) . ?
C14 C19 1.408(11) . ?
C15 C16 1.397(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.399(10) . ?
C17 C20 1.481(11) . ?
C17 C18 1.402(11) . ?
C20 C21 1.349(11) . ?
C23 C24 1.452(13) . ?
C23 C22 1.361(13) . ?
C24 C25 1.403(13) . ?
C24 C29 1.379(12) . ?
C25 H25 0.9300 . ?
C25 C26 1.390(16) . ?
C26 H26 0.9300 . ?
C26 C27 1.350(16) . ?
C27 H27 0.9300 . ?
C27 C28 1.347(15) . ?
C5 C6 1.359(12) . ?
C5 C4 1.378(12) . ?
C6 H6 0.9300 . ?
C6 C7 1.358(10) . ?
C7 C2 1.427(10) . ?
C2 C3 1.397(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(11) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(13) . ?
C22 H22 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.392(15) . ?
C29 H29 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.377(11) . ?
C3 C4 1.366(11) . ?
C4 H4 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
C20 S1 C23 92.6(4) . . ?
C12 C11 Cl4 120.0(7) . . ?
C12 C11 C10 121.0(7) . . ?
C10 C11 Cl4 119.0(8) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(8) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 Cl6 116.2(6) . . ?
C12 C13 C8 121.7(8) . . ?
C8 C13 Cl6 121.7(7) . . ?
C13 C8 C1 121.9(8) . . ?
C9 C8 C13 115.9(7) . . ?
C9 C8 C1 122.2(7) . . ?
C14 C1 C8 121.2(7) . . ?
C2 C1 C8 118.9(7) . . ?
C2 C1 C14 119.8(6) . . ?
C15 C14 C1 122.0(7) . . ?
C15 C14 C19 115.6(7) . . ?
C19 C14 C1 122.2(7) . . ?
C14 C15 Cl8 120.8(7) . . ?
C14 C15 C16 122.6(8) . . ?
C16 C15 Cl8 116.6(7) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(8) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C20 121.2(7) . . ?
C16 C17 C18 117.5(7) . . ?
C18 C17 C20 121.2(7) . . ?
C17 C20 S1 120.7(6) . . ?
C21 C20 S1 112.5(7) . . ?
C21 C20 C17 126.9(8) . . ?
C24 C23 S1 120.2(7) . . ?
C22 C23 S1 107.7(8) . . ?
C22 C23 C24 132.1(9) . . ?
C25 C24 C23 119.4(10) . . ?
C29 C24 C23 123.1(9) . . ?
C29 C24 C25 117.5(10) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.1(12) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(12) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.5(12) . . ?
C28 C27 H27 119.2 . . ?
C6 C5 Cl1 119.8(7) . . ?
C6 C5 C4 120.2(8) . . ?
C4 C5 Cl1 120.0(8) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(8) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 Cl3 117.5(6) . . ?
C6 C7 C2 121.7(7) . . ?
C2 C7 Cl3 120.8(6) . . ?
C7 C2 C1 122.0(7) . . ?
C3 C2 C1 123.0(6) . . ?
C3 C2 C7 115.0(7) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(8) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 Cl7 120.5(7) . . ?
C18 C19 Cl7 116.3(6) . . ?
C18 C19 C14 123.0(8) . . ?
C20 C21 H21 124.5 . . ?
C20 C21 C22 111.1(9) . . ?
C22 C21 H21 124.5 . . ?
C23 C22 C21 116.2(9) . . ?
C23 C22 H22 121.9 . . ?
C21 C22 H22 121.9 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.4(12) . . ?
C29 C28 H28 120.3 . . ?
C24 C29 C28 121.4(10) . . ?
C24 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C11 C10 H10 121.1 . . ?
C9 C10 C11 117.8(8) . . ?
C9 C10 H10 121.1 . . ?
C8 C9 Cl5 120.5(6) . . ?
C8 C9 C10 123.8(8) . . ?
C10 C9 Cl5 115.6(7) . . ?
C2 C3 Cl2 121.1(6) . . ?
C4 C3 Cl2 115.9(6) . . ?
C4 C3 C2 122.9(7) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(8) . . ?
C3 C4 H4 120.3 . . ?

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
Cl4 C11 C12 C13 -178.0(6) . . . . ?
Cl4 C11 C10 C9 176.2(6) . . . . ?
Cl1 C5 C6 C7 -178.2(7) . . . . ?
Cl1 C5 C4 C3 178.8(7) . . . . ?
Cl3 C7 C2 C1 1.6(11) . . . . ?
Cl3 C7 C2 C3 -177.9(6) . . . . ?
Cl8 C15 C16 C17 178.0(5) . . . . ?
Cl6 C13 C8 C1 -1.5(10) . . . . ?
Cl6 C13 C8 C9 -179.5(6) . . . . ?
Cl2 C3 C4 C5 176.5(7) . . . . ?
S1 C20 C21 C22 0.8(10) . . . . ?
S1 C23 C24 C25 173.5(7) . . . . ?
S1 C23 C24 C29 -6.5(12) . . . . ?
S1 C23 C22 C21 1.2(11) . . . . ?
C11 C12 C13 Cl6 177.4(6) . . . . ?
C11 C12 C13 C8 4.4(12) . . . . ?
C11 C10 C9 Cl5 176.3(6) . . . . ?
C11 C10 C9 C8 -0.8(12) . . . . ?
C12 C11 C10 C9 -2.0(12) . . . . ?
C12 C13 C8 C1 171.1(7) . . . . ?
C12 C13 C8 C9 -6.8(11) . . . . ?
C13 C8 C1 C14 50.5(10) . . . . ?
C13 C8 C1 C2 -131.8(8) . . . . ?
C13 C8 C9 Cl5 -171.9(5) . . . . ?
C13 C8 C9 C10 5.1(12) . . . . ?
C8 C1 C14 C15 -133.6(8) . . . . ?
C8 C1 C14 C19 50.4(10) . . . . ?
C8 C1 C2 C7 -134.4(8) . . . . ?
C8 C1 C2 C3 45.0(11) . . . . ?
C1 C8 C9 Cl5 10.1(11) . . . . ?
C1 C8 C9 C10 -172.9(7) . . . . ?
C1 C14 C15 Cl8 8.5(10) . . . . ?
C1 C14 C15 C16 -173.6(7) . . . . ?
C1 C14 C19 Cl7 -2.0(10) . . . . ?
C1 C14 C19 C18 172.8(7) . . . . ?
C1 C2 C3 Cl2 3.9(11) . . . . ?
C1 C2 C3 C4 -179.2(8) . . . . ?
C14 C1 C2 C7 43.2(10) . . . . ?
C14 C1 C2 C3 -137.3(8) . . . . ?
C14 C15 C16 C17 0.1(11) . . . . ?
C15 C14 C19 Cl7 -178.3(6) . . . . ?
C15 C14 C19 C18 -3.5(11) . . . . ?
C15 C16 C17 C20 176.3(7) . . . . ?
C15 C16 C17 C18 -2.3(10) . . . . ?
C16 C17 C20 S1 -2.8(10) . . . . ?
C16 C17 C20 C21 178.0(8) . . . . ?
C16 C17 C18 C19 1.5(11) . . . . ?
C17 C20 C21 C22 -180.0(8) . . . . ?
C17 C18 C19 Cl7 176.5(6) . . . . ?
C17 C18 C19 C14 1.5(12) . . . . ?
C20 S1 C23 C24 -178.0(7) . . . . ?
C20 S1 C23 C22 -0.6(7) . . . . ?
C20 C17 C18 C19 -177.1(7) . . . . ?
C20 C21 C22 C23 -1.3(13) . . . . ?
C23 S1 C20 C17 -179.4(6) . . . . ?
C23 S1 C20 C21 -0.1(7) . . . . ?
C23 C24 C25 C26 -179.5(10) . . . . ?
C23 C24 C29 C28 179.9(9) . . . . ?
C24 C23 C22 C21 178.2(9) . . . . ?
C24 C25 C26 C27 0.7(19) . . . . ?
C25 C24 C29 C28 0.0(14) . . . . ?
C25 C26 C27 C28 -2(2) . . . . ?
C26 C27 C28 C29 2.7(19) . . . . ?
C27 C28 C29 C24 -1.5(17) . . . . ?
C5 C6 C7 Cl3 177.7(7) . . . . ?
C5 C6 C7 C2 -0.6(13) . . . . ?
C6 C5 C4 C3 0.2(14) . . . . ?
C6 C7 C2 C1 179.8(7) . . . . ?
C6 C7 C2 C3 0.3(11) . . . . ?
C7 C2 C3 Cl2 -176.6(6) . . . . ?
C7 C2 C3 C4 0.3(12) . . . . ?
C2 C1 C14 C15 48.8(10) . . . . ?
C2 C1 C14 C19 -127.3(8) . . . . ?
C2 C3 C4 C5 -0.6(14) . . . . ?
C18 C17 C20 S1 175.7(6) . . . . ?
C18 C17 C20 C21 -3.5(12) . . . . ?
C19 C14 C15 Cl8 -175.2(6) . . . . ?
C19 C14 C15 C16 2.7(11) . . . . ?
C22 C23 C24 C25 -3.2(15) . . . . ?
C22 C23 C24 C29 176.8(10) . . . . ?
C29 C24 C25 C26 0.5(15) . . . . ?
C10 C11 C12 C13 0.2(12) . . . . ?
C9 C8 C1 C14 -131.6(8) . . . . ?
C9 C8 C1 C2 46.0(10) . . . . ?
C4 C5 C6 C7 0.4(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/water'
