# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1534939'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 O2 S2 Tl'
_chemical_formula_weight         403.63

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'
N N 0.0061 0.0033 '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'
Tl Tl -2.8358 9.6688 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   4.2030(10)
_cell_length_b                   8.045(2)
_cell_length_c                   14.929(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.16(2)
_cell_angle_gamma                90
_cell_volume                     504.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9305
_cell_measurement_theta_min      2.729
_cell_measurement_theta_max      28.383

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.656
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    16.376
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3358
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest SCM Diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9305
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.729
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2354
_reflns_number_gt                2270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1102P)²+0.7359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2354
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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_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
Tl1 Tl 0.02111(10) 0.54944(16) 0.07102(3) 0.0378(3) Uani 1 1 d . . . . .
O11 O 0.450(4) 0.526(2) 0.2161(8) 0.056(4) Uani 1 1 d . . . . .
C12 C 0.592(4) 0.422(2) 0.2618(10) 0.034(3) Uani 1 1 d . . . . .
C13 C 0.696(4) 0.256(2) 0.2406(10) 0.035(3) Uani 1 1 d . . . . .
H13 H 0.800775 0.194105 0.286835 0.042 Uiso 1 1 calc R U . . .
C14 C 0.655(4) 0.181(2) 0.1606(9) 0.029(3) Uani 1 1 d . . . . .
S15 S 0.5057(8) 0.2587(6) 0.0589(3) 0.0323(8) Uani 1 1 d . . . . .
S16 S 0.7717(12) -0.0281(6) 0.1448(3) 0.0407(9) Uani 1 1 d . . . . .
C17 C 0.974(6) -0.089(3) 0.2477(13) 0.053(5) Uani 1 1 d . . . . .
H17A H 0.991891 -0.210827 0.249841 0.079 Uiso 1 1 calc R U . . .
H17B H 0.853370 -0.050369 0.298992 0.079 Uiso 1 1 calc R U . . .
H17C H 1.187770 -0.040245 0.249891 0.079 Uiso 1 1 calc R U . . .
C21 C 0.657(3) 0.473(2) 0.3580(10) 0.031(3) Uani 1 1 d . . . . .
O22 O 0.846(3) 0.3776(17) 0.4134(8) 0.044(3) Uani 1 1 d . . . . .
C23 C 0.858(5) 0.449(3) 0.4970(11) 0.044(4) Uani 1 1 d . . . . .
H23 H 0.972590 0.408659 0.547888 0.052 Uiso 1 1 calc R U . . .
C24 C 0.678(5) 0.588(3) 0.4939(12) 0.048(5) Uani 1 1 d . . . . .
H24 H 0.644922 0.661684 0.542450 0.058 Uiso 1 1 calc R U . . .
C25 C 0.546(5) 0.605(3) 0.4056(16) 0.052(4) Uani 1 1 d . . . . .
H25 H 0.408633 0.691115 0.384287 0.062 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
Tl1 O11 2.795(12) . ?
Tl1 S15 3.109(4) . ?
Tl1 S15 3.191(5) 1_455 ?
Tl1 O11 3.271(17) 1_455 ?
Tl1 S15 3.273(4) 2_655 ?
Tl1 S15 3.366(4) 2 ?
Tl1 S16 3.411(5) 2_655 ?
Tl1 S16 3.729(5) 1_465 ?
Tl1 Tl1 4.2030(10) 1_655 ?
Tl1 Tl1 4.2030(10) 1_455 ?
Tl1 Tl1 4.5489(10) 2_545 ?
Tl1 Tl1 4.5489(10) 2 ?
O11 C12 1.23(2) . ?
C12 C13 1.45(2) . ?
C12 C21 1.51(2) . ?
C13 C14 1.35(2) . ?
C13 H13 0.9500 . ?
C14 S15 1.747(13) . ?
C14 S16 1.767(18) . ?
S16 C17 1.810(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 O22 1.37(2) . ?
C21 C25 1.37(3) . ?
O22 C23 1.38(2) . ?
C23 C24 1.35(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.43(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
O11 Tl1 S15 65.2(3) . . ?
O11 Tl1 S15 114.9(4) . 1_455 ?
S15 Tl1 S15 83.69(13) . 1_455 ?
O11 Tl1 O11 87.3(4) . 1_455 ?
S15 Tl1 O11 119.0(3) . 1_455 ?
S15 Tl1 O11 59.2(3) 1_455 1_455 ?
O11 Tl1 S15 96.0(4) . 2_655 ?
S15 Tl1 S15 86.90(5) . 2_655 ?
S15 Tl1 S15 139.79(6) 1_455 2_655 ?
O11 Tl1 S15 152.3(3) 1_455 2_655 ?
O11 Tl1 S15 152.5(4) . 2 ?
S15 Tl1 S15 140.09(7) . 2 ?
S15 Tl1 S15 84.04(5) 1_455 2 ?
O11 Tl1 S15 85.8(2) 1_455 2 ?
S15 Tl1 S15 78.55(9) 2_655 2 ?
O11 Tl1 S16 123.1(3) . 2_655 ?
S15 Tl1 S16 68.14(11) . 2_655 ?
S15 Tl1 S16 89.92(10) 1_455 2_655 ?
O11 Tl1 S16 145.0(2) 1_455 2_655 ?
S15 Tl1 S16 50.54(11) 2_655 2_655 ?
S15 Tl1 S16 74.02(11) 2 2_655 ?
O11 Tl1 S16 90.8(4) . 1_465 ?
S15 Tl1 S16 153.01(10) . 1_465 ?
S15 Tl1 S16 119.35(11) 1_455 1_465 ?
O11 Tl1 S16 69.1(3) 1_455 1_465 ?
S15 Tl1 S16 83.34(12) 2_655 1_465 ?
S15 Tl1 S16 61.88(11) 2 1_465 ?
S16 Tl1 S16 121.60(13) 2_655 1_465 ?
O11 Tl1 Tl1 51.0(4) . 1_655 ?
S15 Tl1 Tl1 48.98(8) . 1_655 ?
S15 Tl1 Tl1 132.68(8) 1_455 1_655 ?
O11 Tl1 Tl1 138.4(2) 1_455 1_655 ?
S15 Tl1 Tl1 51.70(7) 2_655 1_655 ?
S15 Tl1 Tl1 130.25(7) 2 1_655 ?
S16 Tl1 Tl1 74.07(8) 2_655 1_655 ?
S16 Tl1 Tl1 106.68(8) 1_465 1_655 ?
O11 Tl1 Tl1 129.0(4) . 1_455 ?
S15 Tl1 Tl1 131.02(8) . 1_455 ?
S15 Tl1 Tl1 47.32(8) 1_455 1_455 ?
O11 Tl1 Tl1 41.6(2) 1_455 1_455 ?
S15 Tl1 Tl1 128.30(7) 2_655 1_455 ?
S15 Tl1 Tl1 49.75(7) 2 1_455 ?
S16 Tl1 Tl1 105.92(8) 2_655 1_455 ?
S16 Tl1 Tl1 73.32(8) 1_465 1_455 ?
Tl1 Tl1 Tl1 180.0 1_655 1_455 ?
O11 Tl1 Tl1 108.6(4) . 2_545 ?
S15 Tl1 Tl1 47.71(8) . 2_545 ?
S15 Tl1 Tl1 46.01(7) 1_455 2_545 ?
O11 Tl1 Tl1 103.6(3) 1_455 2_545 ?
S15 Tl1 Tl1 101.36(9) 2_655 2_545 ?
S15 Tl1 Tl1 98.90(9) 2 2_545 ?
S16 Tl1 Tl1 53.59(8) 2_655 2_545 ?
S16 Tl1 Tl1 159.21(7) 1_465 2_545 ?
Tl1 Tl1 Tl1 91.695(14) 1_655 2_545 ?
Tl1 Tl1 Tl1 88.305(14) 1_455 2_545 ?
O11 Tl1 Tl1 116.1(4) . 2 ?
S15 Tl1 Tl1 131.12(9) . 2 ?
S15 Tl1 Tl1 127.00(8) 1_455 2 ?
O11 Tl1 Tl1 109.7(3) 1_455 2 ?
S15 Tl1 Tl1 44.54(8) 2_655 2 ?
S15 Tl1 Tl1 43.11(8) 2 2 ?
S16 Tl1 Tl1 74.33(9) 2_655 2 ?
S16 Tl1 Tl1 47.40(8) 1_465 2 ?
Tl1 Tl1 Tl1 91.694(14) 1_655 2 ?
Tl1 Tl1 Tl1 88.305(14) 1_455 2 ?
Tl1 Tl1 Tl1 124.32(3) 2_545 2 ?
C12 O11 Tl1 141.0(13) . . ?
C12 O11 Tl1 93.0(11) . 1_655 ?
Tl1 O11 Tl1 87.3(4) . 1_655 ?
O11 C12 C13 130.8(16) . . ?
O11 C12 C21 115.0(15) . . ?
C13 C12 C21 114.0(14) . . ?
C14 C13 C12 125.1(15) . . ?
C14 C13 H13 117.4 . . ?
C12 C13 H13 117.4 . . ?
C13 C14 S15 130.3(14) . . ?
C13 C14 S16 120.9(11) . . ?
S15 C14 S16 108.8(8) . . ?
C14 S15 Tl1 116.4(6) . . ?
C14 S15 Tl1 89.1(5) . 1_655 ?
Tl1 S15 Tl1 83.69(13) . 1_655 ?
C14 S15 Tl1 96.8(6) . 2_645 ?
Tl1 S15 Tl1 145.90(15) . 2_645 ?
Tl1 S15 Tl1 89.46(10) 1_655 2_645 ?
C14 S15 Tl1 122.7(6) . 2_545 ?
Tl1 S15 Tl1 89.18(9) . 2_545 ?
Tl1 S15 Tl1 146.85(15) 1_655 2_545 ?
Tl1 S15 Tl1 78.55(9) 2_645 2_545 ?
C14 S16 C17 105.8(9) . . ?
C14 S16 Tl1 91.7(5) . 2_645 ?
C17 S16 Tl1 136.6(9) . 2_645 ?
C14 S16 Tl1 170.5(5) . 1_645 ?
C17 S16 Tl1 82.6(7) . 1_645 ?
Tl1 S16 Tl1 79.00(9) 2_645 1_645 ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O22 C21 C25 108.8(15) . . ?
O22 C21 C12 121.0(14) . . ?
C25 C21 C12 130.2(16) . . ?
C21 O22 C23 108.8(14) . . ?
C24 C23 O22 107.9(16) . . ?
C24 C23 H23 126.1 . . ?
O22 C23 H23 126.1 . . ?
C25 C24 C23 108.8(16) . . ?
C25 C24 H24 125.6 . . ?
C23 C24 H24 125.6 . . ?
C24 C25 C21 105.8(17) . . ?
C24 C25 H25 127.1 . . ?
C21 C25 H25 127.1 . . ?

_refine_diff_density_max         1.983
_refine_diff_density_min         -2.064
_refine_diff_density_rms         0.306

####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 1534942'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Cl3 O3 S6 Tl3'
_chemical_formula_weight         1344.31

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'
N N 0.0061 0.0033 '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'
Tl Tl -2.8358 9.6688 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   16.4850(11)
_cell_length_b                   18.2914(10)
_cell_length_c                   12.6565(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.753(8)
_cell_angle_gamma                90
_cell_volume                     3568.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13164
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.502
_exptl_crystal_F_000             2472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    14.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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       'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            13164
_diffrn_reflns_av_unetI/netI     0.1308
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.408
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             7863
_reflns_number_gt                5122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-97, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1057P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7863
_refine_ls_number_parameters     409
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2103
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.001
_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_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
Tl1 Tl 0.01598(5) 0.09273(3) 0.35817(5) 0.0244(2) Uani 1 1 d . . . . .
Tl2 Tl -0.03504(5) 0.07294(3) 0.82452(5) 0.0241(2) Uani 1 1 d . . . . .
Tl3 Tl 0.00741(5) 0.25506(3) 0.53713(5) 0.0276(2) Uani 1 1 d . . . . .
O11 O 0.1058(8) 0.1175(6) 0.9874(9) 0.026(3) Uani 1 1 d . . . . .
C12 C 0.1791(11) 0.1397(8) 1.0005(11) 0.017(3) Uani 1 1 d . U . . .
C13 C 0.2014(11) 0.1992(8) 0.9423(12) 0.017(3) Uani 1 1 d . . . . .
H13 H 0.259342 0.213196 0.966070 0.020 Uiso 1 1 calc R U . . .
C14 C 0.1441(10) 0.2367(7) 0.8551(11) 0.010(3) Uani 1 1 d . U . . .
S15 S 0.0344(3) 0.2279(2) 0.7923(3) 0.0280(11) Uani 1 1 d . . . . .
S16 S 0.1805(3) 0.3089(2) 0.7878(3) 0.0242(10) Uani 1 1 d . . . . .
C17 C 0.2960(12) 0.3148(9) 0.8602(12) 0.023(4) Uani 1 1 d . . . . .
H17A H 0.308620 0.316692 0.940283 0.035 Uiso 1 1 calc R U . . .
H17B H 0.317694 0.358106 0.836593 0.035 Uiso 1 1 calc R U . . .
H17C H 0.323405 0.272565 0.842460 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2568(12) 0.0997(8) 1.0869(11) 0.017(4) Uani 1 1 d . . . . .
C23 C 0.2358(13) 0.0435(9) 1.1461(12) 0.028(4) Uani 1 1 d . . . . .
H23 H 0.177553 0.033388 1.131404 0.033 Uiso 1 1 calc R U . . .
C24 C 0.2969(11) 0.0023(8) 1.2252(12) 0.018(3) Uani 1 1 d . . . . .
H24 H 0.280399 -0.034718 1.263803 0.021 Uiso 1 1 calc R U . . .
C25 C 0.3824(15) 0.0163(9) 1.2463(13) 0.034(5) Uani 1 1 d . . . . .
C26 C 0.4077(13) 0.0715(9) 1.1893(13) 0.026(4) Uani 1 1 d . . . . .
H26 H 0.466197 0.080053 1.203233 0.031 Uiso 1 1 calc R U . . .
C27 C 0.3428(13) 0.1149(9) 1.1089(13) 0.028(4) Uani 1 1 d . . . . .
H27 H 0.358594 0.153189 1.071819 0.033 Uiso 1 1 calc R U . . .
Cl27 Cl 0.4623(3) -0.0363(3) 1.3435(3) 0.0358(12) Uani 1 1 d . . . . .
O31 O -0.1272(8) 0.1798(6) 0.3418(9) 0.021(3) Uani 1 1 d . . . . .
C32 C -0.1992(11) 0.1611(8) 0.3274(11) 0.015(3) Uani 1 1 d . U . . .
C33 C -0.2237(11) 0.1059(8) 0.3905(12) 0.019(3) Uani 1 1 d . . . . .
H33 H -0.281862 0.092461 0.363572 0.022 Uiso 1 1 calc R U . . .
C34 C -0.1727(13) 0.0710(9) 0.4841(12) 0.026(4) Uani 1 1 d . . . . .
S35 S -0.0636(3) 0.0798(2) 0.5539(3) 0.0261(10) Uani 1 1 d . . . . .
S36 S -0.2134(3) 0.0055(2) 0.5529(3) 0.0254(10) Uani 1 1 d . . . . .
C37 C -0.3292(12) -0.0021(10) 0.4738(13) 0.028(4) Uani 1 1 d . . . . .
H37A H -0.356115 0.044794 0.471203 0.043 Uiso 1 1 calc R U . . .
H37B H -0.354376 -0.036715 0.510230 0.043 Uiso 1 1 calc R U . . .
H37C H -0.338244 -0.018205 0.398342 0.043 Uiso 1 1 calc R U . . .
C41 C -0.2736(13) 0.2006(8) 0.2346(12) 0.026(4) Uani 1 1 d . . . . .
C42 C -0.2463(12) 0.2602(9) 0.1815(12) 0.021(4) Uani 1 1 d . . . . .
H42 H -0.187947 0.271903 0.200657 0.025 Uiso 1 1 calc R U . . .
C43 C -0.3118(14) 0.3007(9) 0.0986(13) 0.034(5) Uani 1 1 d . . . . .
H43 H -0.296403 0.342696 0.068758 0.041 Uiso 1 1 calc R U . . .
C44 C -0.3945(12) 0.2805(9) 0.0623(13) 0.021(3) Uani 1 1 d . U . . .
C45 C -0.4192(13) 0.2228(9) 0.1143(13) 0.026(4) Uani 1 1 d . U . . .
H45 H -0.477689 0.211095 0.093512 0.032 Uiso 1 1 calc R U . . .
C46 C -0.3589(13) 0.1827(9) 0.1960(13) 0.027(4) Uani 1 1 d . . . . .
H46 H -0.376924 0.142013 0.225905 0.032 Uiso 1 1 calc R U . . .
Cl47 Cl -0.4716(4) 0.3270(2) -0.0471(3) 0.0364(12) Uani 1 1 d . . . . .
O51 O -0.0999(11) -0.0132(7) 0.2399(10) 0.045(4) Uani 1 1 d . . . . .
C52 C -0.1756(15) -0.0014(9) 0.1843(13) 0.029(5) Uani 1 1 d . . . . .
C53 C -0.2043(12) 0.0539(9) 0.0982(12) 0.022(4) Uani 1 1 d . . . . .
H53 H -0.263645 0.063080 0.070500 0.026 Uiso 1 1 calc R U . . .
C54 C -0.1581(11) 0.0933(8) 0.0534(11) 0.014(3) Uani 1 1 d . U . . .
S55 S -0.0449(4) 0.0893(2) 0.0850(3) 0.0273(10) Uani 1 1 d . . . . .
S56 S -0.2000(3) 0.1569(2) -0.0551(3) 0.0286(11) Uani 1 1 d . . . . .
C57 C -0.3175(11) 0.1547(9) -0.0879(14) 0.023(4) Uani 1 1 d . . . . .
H57A H -0.339557 0.107302 -0.116715 0.034 Uiso 1 1 calc R U . . .
H57B H -0.344812 0.191196 -0.143647 0.034 Uiso 1 1 calc R U . . .
H57C H -0.329787 0.164337 -0.020521 0.034 Uiso 1 1 calc R U . . .
C61 C -0.2401(10) -0.0484(8) 0.2114(11) 0.013(3) Uani 1 1 d . U . . .
C62 C -0.2100(14) -0.0990(10) 0.2962(13) 0.032(5) Uani 1 1 d . . . . .
H62 H -0.150809 -0.101379 0.337290 0.039 Uiso 1 1 calc R U . . .
C63 C -0.2666(15) -0.1480(9) 0.3231(13) 0.033(5) Uani 1 1 d . . . . .
H63 H -0.245044 -0.182686 0.379862 0.040 Uiso 1 1 calc R U . . .
C64 C -0.3528(12) -0.1430(8) 0.2641(12) 0.020(4) Uani 1 1 d . . . . .
C65 C -0.3907(13) -0.0924(10) 0.1756(14) 0.031(4) Uani 1 1 d . . . . .
H65 H -0.450180 -0.089820 0.136229 0.037 Uiso 1 1 calc R U . . .
C66 C -0.3297(12) -0.0457(8) 0.1522(13) 0.023(4) Uani 1 1 d . . . . .
H66 H -0.350622 -0.011622 0.094407 0.028 Uiso 1 1 calc R U . . .
Cl67 Cl -0.4254(4) -0.2004(2) 0.2979(4) 0.0426(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tl1 O51 2.760(14) . ?
Tl1 O31 2.794(12) . ?
Tl1 S35 3.196(4) . ?
Tl1 S55 3.241(4) . ?
Tl1 S35 3.345(4) 3_556 ?
Tl1 S15 3.424(4) 4_565 ?
Tl1 S36 3.534(5) 3_556 ?
Tl1 S16 3.618(5) 4_565 ?
Tl1 Tl3 3.7674(8) . ?
Tl1 Tl2 3.8913(9) 3_556 ?
Tl1 Tl3 4.8862(9) 4_565 ?
Tl2 O11 2.629(12) . ?
Tl2 O51 2.845(16) 3_556 ?
Tl2 S15 3.137(4) . ?
Tl2 S55 3.283(4) 3_556 ?
Tl2 S35 3.291(4) . ?
Tl2 S55 3.371(4) 1_556 ?
Tl2 Tl3 4.0365(9) 4_566 ?
Tl3 O31 3.008(11) . ?
Tl3 O11 3.031(12) 4_565 ?
Tl3 S55 3.097(4) 4_566 ?
Tl3 S15 3.139(4) . ?
Tl3 S15 3.297(4) 4_565 ?
Tl3 S35 3.445(4) . ?
Tl3 S16 3.572(4) . ?
Tl3 S56 3.581(5) 4_566 ?
O11 C12 1.228(19) . ?
C12 C13 1.43(2) . ?
C12 C22 1.54(2) . ?
C13 C14 1.36(2) . ?
C13 H13 0.9300 . ?
C14 S15 1.706(16) . ?
C14 S16 1.787(14) . ?
S16 C17 1.801(18) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C22 C23 1.39(2) . ?
C22 C27 1.37(3) . ?
C23 C24 1.37(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.36(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.39(2) . ?
C25 Cl27 1.739(19) . ?
C26 C27 1.43(2) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
O31 C32 1.186(19) . ?
C32 C33 1.43(2) . ?
C32 C41 1.54(2) . ?
C33 C34 1.35(2) . ?
C33 H33 0.9300 . ?
C34 S35 1.71(2) . ?
C34 S36 1.749(16) . ?
S36 C37 1.820(18) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C41 C46 1.36(3) . ?
C41 C42 1.43(2) . ?
C42 C43 1.42(2) . ?
C42 H42 0.9300 . ?
C43 C44 1.33(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.38(2) . ?
C44 Cl47 1.735(17) . ?
C45 C46 1.37(2) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
O51 C52 1.22(2) . ?
C52 C53 1.44(2) . ?
C52 C61 1.50(2) . ?
C53 C54 1.31(2) . ?
C53 H53 0.9300 . ?
C54 S56 1.745(14) . ?
C54 S55 1.766(17) . ?
S56 C57 1.832(17) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C61 C62 1.37(2) . ?
C61 C66 1.40(2) . ?
C62 C63 1.42(3) . ?
C62 H62 0.9300 . ?
C63 C64 1.35(3) . ?
C63 H63 0.9300 . ?
C64 C65 1.42(2) . ?
C64 Cl67 1.755(16) . ?
C65 C66 1.43(2) . ?
C65 H65 0.9300 . ?
C66 H66 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
O51 Tl1 O31 87.5(4) . . ?
O51 Tl1 S35 88.5(3) . . ?
O31 Tl1 S35 62.1(2) . . ?
O51 Tl1 S55 61.0(3) . . ?
O31 Tl1 S55 89.9(2) . . ?
S35 Tl1 S55 140.21(13) . . ?
O51 Tl1 S35 63.5(3) . 3_556 ?
O31 Tl1 S35 130.9(2) . 3_556 ?
S35 Tl1 S35 77.55(13) . 3_556 ?
S55 Tl1 S35 106.49(10) . 3_556 ?
O51 Tl1 S15 130.1(3) . 4_565 ?
O31 Tl1 S15 65.3(2) . 4_565 ?
S35 Tl1 S15 110.84(11) . 4_565 ?
S55 Tl1 S15 77.27(9) . 4_565 ?
S35 Tl1 S15 162.55(13) 3_556 4_565 ?
O51 Tl1 S36 101.4(3) . 3_556 ?
O31 Tl1 S36 166.4(2) . 3_556 ?
S35 Tl1 S36 107.46(11) . 3_556 ?
S55 Tl1 S36 103.40(11) . 3_556 ?
S35 Tl1 S36 48.23(11) 3_556 3_556 ?
S15 Tl1 S36 114.42(12) 4_565 3_556 ?
O51 Tl1 S16 130.6(3) . 4_565 ?
O31 Tl1 S16 112.7(2) . 4_565 ?
S35 Tl1 S16 140.96(10) . 4_565 ?
S55 Tl1 S16 73.92(11) . 4_565 ?
S35 Tl1 S16 116.30(11) 3_556 4_565 ?
S15 Tl1 S16 47.56(11) 4_565 4_565 ?
S36 Tl1 S16 69.22(10) 3_556 4_565 ?
O51 Tl1 Tl3 135.5(3) . . ?
O31 Tl1 Tl3 52.0(2) . . ?
S35 Tl1 Tl3 58.62(8) . . ?
S55 Tl1 Tl3 126.40(8) . . ?
S35 Tl1 Tl3 126.70(7) 3_556 . ?
S15 Tl1 Tl3 54.32(7) 4_565 . ?
S36 Tl1 Tl3 115.83(7) 3_556 . ?
S16 Tl1 Tl3 86.97(6) 4_565 . ?
O51 Tl1 Tl2 46.9(3) . 3_556 ?
O31 Tl1 Tl2 130.1(2) . 3_556 ?
S35 Tl1 Tl2 122.99(8) . 3_556 ?
S55 Tl1 Tl2 53.88(8) . 3_556 ?
S35 Tl1 Tl2 53.45(7) 3_556 3_556 ?
S15 Tl1 Tl2 124.65(7) 4_565 3_556 ?
S36 Tl1 Tl2 62.24(7) 3_556 3_556 ?
S16 Tl1 Tl2 90.89(6) 4_565 3_556 ?
Tl3 Tl1 Tl2 177.57(3) . 3_556 ?
O51 Tl1 Tl3 98.0(2) . 4_565 ?
O31 Tl1 Tl3 80.7(2) . 4_565 ?
S35 Tl1 Tl3 141.99(8) . 4_565 ?
S55 Tl1 Tl3 38.49(7) . 4_565 ?
S35 Tl1 Tl3 138.45(7) 3_556 4_565 ?
S15 Tl1 Tl3 39.71(6) 4_565 4_565 ?
S36 Tl1 Tl3 107.84(7) 3_556 4_565 ?
S16 Tl1 Tl3 46.80(7) 4_565 4_565 ?
Tl3 Tl1 Tl3 93.134(13) . 4_565 ?
Tl2 Tl1 Tl3 86.228(16) 3_556 4_565 ?
O11 Tl2 O51 77.3(4) . 3_556 ?
O11 Tl2 S15 63.9(2) . . ?
O51 Tl2 S15 87.2(3) 3_556 . ?
O11 Tl2 S55 82.7(3) . 3_556 ?
O51 Tl2 S55 59.7(3) 3_556 3_556 ?
S15 Tl2 S55 137.91(14) . 3_556 ?
O11 Tl2 S35 124.4(3) . . ?
O51 Tl2 S35 63.5(3) 3_556 . ?
S15 Tl2 S35 75.79(10) . . ?
S55 Tl2 S35 106.79(10) 3_556 . ?
O11 Tl2 S55 62.7(3) . 1_556 ?
O51 Tl2 S55 128.9(3) 3_556 1_556 ?
S15 Tl2 S55 101.15(10) . 1_556 ?
S55 Tl2 S55 83.77(11) 3_556 1_556 ?
S35 Tl2 S55 167.43(13) . 1_556 ?
O11 Tl2 Tl1 118.2(3) . 3_556 ?
O51 Tl2 Tl1 45.1(3) 3_556 3_556 ?
S15 Tl2 Tl1 121.10(8) . 3_556 ?
S55 Tl2 Tl1 52.88(7) 3_556 3_556 ?
S35 Tl2 Tl1 54.76(8) . 3_556 ?
S55 Tl2 Tl1 133.79(7) 1_556 3_556 ?
O11 Tl2 Tl3 48.7(3) . 4_566 ?
O51 Tl2 Tl3 121.5(3) 3_556 4_566 ?
S15 Tl2 Tl3 52.94(7) . 4_566 ?
S55 Tl2 Tl3 121.23(7) 3_556 4_566 ?
S35 Tl2 Tl3 126.25(8) . 4_566 ?
S55 Tl2 Tl3 48.40(7) 1_556 4_566 ?
Tl1 Tl2 Tl3 166.31(3) 3_556 4_566 ?
O31 Tl3 O11 118.4(3) . 4_565 ?
O31 Tl3 S55 114.0(2) . 4_566 ?
O11 Tl3 S55 62.6(2) 4_565 4_566 ?
O31 Tl3 S15 124.6(2) . . ?
O11 Tl3 S15 116.4(2) 4_565 . ?
S55 Tl3 S15 83.78(10) 4_566 . ?
O31 Tl3 S15 65.0(2) . 4_565 ?
O11 Tl3 S15 58.1(2) 4_565 4_565 ?
S55 Tl3 S15 103.70(10) 4_566 4_565 ?
S15 Tl3 S15 164.70(19) . 4_565 ?
O31 Tl3 S35 57.1(2) . . ?
O11 Tl3 S35 161.3(2) 4_565 . ?
S55 Tl3 S35 136.01(13) 4_566 . ?
S15 Tl3 S35 73.56(10) . . ?
S15 Tl3 S35 107.91(10) 4_565 . ?
O31 Tl3 S16 168.8(2) . . ?
O11 Tl3 S16 69.8(2) 4_565 . ?
S55 Tl3 S16 76.26(11) 4_566 . ?
S15 Tl3 S16 49.65(12) . . ?
S15 Tl3 S16 118.53(11) 4_565 . ?
S35 Tl3 S16 112.57(9) . . ?
O31 Tl3 S56 66.2(2) . 4_566 ?
O11 Tl3 S56 96.1(2) 4_565 4_566 ?
S55 Tl3 S56 49.48(12) 4_566 4_566 ?
S15 Tl3 S56 100.21(12) . 4_566 ?
S15 Tl3 S56 94.72(11) 4_565 4_566 ?
S35 Tl3 S56 97.63(11) . 4_566 ?
S16 Tl3 S56 122.37(9) . 4_566 ?
O31 Tl3 Tl1 47.1(2) . . ?
O11 Tl3 Tl1 110.2(2) 4_565 . ?
S55 Tl3 Tl1 156.17(8) 4_566 . ?
S15 Tl3 Tl1 118.17(8) . . ?
S15 Tl3 Tl1 57.53(7) 4_565 . ?
S35 Tl3 Tl1 52.37(7) . . ?
S16 Tl3 Tl1 124.27(7) . . ?
S56 Tl3 Tl1 113.16(7) 4_566 . ?
O31 Tl3 Tl2 84.6(2) . 4_565 ?
O11 Tl3 Tl2 40.6(2) 4_565 4_565 ?
S55 Tl3 Tl2 54.50(7) 4_566 4_565 ?
S15 Tl3 Tl2 137.46(8) . 4_565 ?
S15 Tl3 Tl2 49.40(8) 4_565 4_565 ?
S35 Tl3 Tl2 141.62(7) . 4_565 ?
S16 Tl3 Tl2 105.80(6) . 4_565 ?
S56 Tl3 Tl2 60.80(7) 4_566 4_565 ?
Tl1 Tl3 Tl2 104.365(18) . 4_565 ?
O31 Tl3 Tl1 137.7(2) . 4_566 ?
O11 Tl3 Tl1 82.78(19) 4_565 4_566 ?
S55 Tl3 Tl1 40.65(7) 4_566 4_566 ?
S15 Tl3 Tl1 44.18(8) . 4_566 ?
S15 Tl3 Tl1 138.93(7) 4_565 4_566 ?
S35 Tl3 Tl1 112.92(7) . 4_566 ?
S16 Tl3 Tl1 47.59(7) . 4_566 ?
S56 Tl3 Tl1 75.98(6) 4_566 4_566 ?
Tl1 Tl3 Tl1 162.335(19) . 4_566 ?
Tl2 Tl3 Tl1 93.286(17) 4_565 4_566 ?
C12 O11 Tl2 139.6(9) . . ?
C12 O11 Tl3 106.9(10) . 4_566 ?
Tl2 O11 Tl3 90.7(4) . 4_566 ?
O11 C12 C13 126.9(15) . . ?
O11 C12 C22 118.0(14) . . ?
C13 C12 C22 115.1(15) . . ?
C14 C13 C12 124.7(15) . . ?
C14 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
C13 C14 S15 130.5(12) . . ?
C13 C14 S16 120.4(12) . . ?
S15 C14 S16 109.0(7) . . ?
C14 S15 Tl2 113.5(5) . . ?
C14 S15 Tl3 101.8(5) . . ?
Tl2 S15 Tl3 110.57(13) . . ?
C14 S15 Tl3 91.5(5) . 4_566 ?
Tl2 S15 Tl3 77.66(10) . 4_566 ?
Tl3 S15 Tl3 159.19(17) . 4_566 ?
C14 S15 Tl1 88.1(5) . 4_566 ?
Tl2 S15 Tl1 140.01(16) . 4_566 ?
Tl3 S15 Tl1 96.12(10) . 4_566 ?
Tl3 S15 Tl1 68.15(8) 4_566 4_566 ?
C14 S16 C17 105.9(7) . . ?
C14 S16 Tl3 85.5(5) . . ?
C17 S16 Tl3 146.7(5) . . ?
C14 S16 Tl1 81.0(5) . 4_566 ?
C17 S16 Tl1 126.5(5) . 4_566 ?
Tl3 S16 Tl1 85.61(11) . 4_566 ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C22 C27 118.5(16) . . ?
C23 C22 C12 115.6(16) . . ?
C27 C22 C12 125.9(14) . . ?
C24 C23 C22 123.0(18) . . ?
C24 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
C23 C24 C25 118.8(15) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C24 C25 C26 121.0(17) . . ?
C24 C25 Cl27 120.4(12) . . ?
C26 C25 Cl27 118.6(17) . . ?
C25 C26 C27 119.2(18) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C22 C27 C26 119.4(15) . . ?
C22 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C32 O31 Tl1 128.4(10) . . ?
C32 O31 Tl3 131.7(9) . . ?
Tl1 O31 Tl3 80.9(3) . . ?
O31 C32 C33 125.6(15) . . ?
O31 C32 C41 117.7(14) . . ?
C33 C32 C41 116.8(15) . . ?
C34 C33 C32 127.9(16) . . ?
C34 C33 H33 116.0 . . ?
C32 C33 H33 116.0 . . ?
C33 C34 S35 128.7(14) . . ?
C33 C34 S36 122.3(15) . . ?
S35 C34 S36 109.1(9) . . ?
C34 S35 Tl1 104.6(5) . . ?
C34 S35 Tl2 105.7(5) . . ?
Tl1 S35 Tl2 149.67(17) . . ?
C34 S35 Tl1 99.4(6) . 3_556 ?
Tl1 S35 Tl1 102.45(13) . 3_556 ?
Tl2 S35 Tl1 71.80(8) . 3_556 ?
C34 S35 Tl3 112.0(6) . . ?
Tl1 S35 Tl3 69.01(8) . . ?
Tl2 S35 Tl3 99.97(11) . . ?
Tl1 S35 Tl3 148.60(16) 3_556 . ?
C34 S36 C37 106.9(9) . . ?
C34 S36 Tl1 92.0(7) . 3_556 ?
C37 S36 Tl1 143.6(6) . 3_556 ?
S36 C37 H37A 109.5 . . ?
S36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
S36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C46 C41 C42 118.2(15) . . ?
C46 C41 C32 127.1(15) . . ?
C42 C41 C32 114.6(16) . . ?
C43 C42 C41 117.4(17) . . ?
C43 C42 H42 121.3 . . ?
C41 C42 H42 121.3 . . ?
C44 C43 C42 122.0(16) . . ?
C44 C43 H43 119.0 . . ?
C42 C43 H43 119.0 . . ?
C43 C44 C45 119.3(16) . . ?
C43 C44 Cl47 120.7(13) . . ?
C45 C44 Cl47 120.0(14) . . ?
C46 C45 C44 120.9(18) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C41 C46 C45 121.8(17) . . ?
C41 C46 H46 119.1 . . ?
C45 C46 H46 119.1 . . ?
C52 O51 Tl1 124.1(11) . . ?
C52 O51 Tl2 130.5(11) . 3_556 ?
Tl1 O51 Tl2 87.9(5) . 3_556 ?
O51 C52 C53 123.9(19) . . ?
O51 C52 C61 115.6(15) . . ?
C53 C52 C61 120.5(18) . . ?
C54 C53 C52 128.9(19) . . ?
C54 C53 H53 115.6 . . ?
C52 C53 H53 115.6 . . ?
C53 C54 S56 125.2(14) . . ?
C53 C54 S55 127.3(13) . . ?
S56 C54 S55 107.4(9) . . ?
C54 S55 Tl3 105.2(5) . 4_565 ?
C54 S55 Tl1 98.3(5) . . ?
Tl3 S55 Tl1 100.86(12) 4_565 . ?
C54 S55 Tl2 112.2(5) . 3_556 ?
Tl3 S55 Tl2 142.56(19) 4_565 3_556 ?
Tl1 S55 Tl2 73.23(8) . 3_556 ?
C54 S55 Tl2 101.3(5) . 1_554 ?
Tl3 S55 Tl2 77.10(9) 4_565 1_554 ?
Tl1 S55 Tl2 160.21(19) . 1_554 ?
Tl2 S55 Tl2 96.23(11) 3_556 1_554 ?
C54 S56 C57 104.8(8) . . ?
C54 S56 Tl3 88.7(6) . 4_565 ?
C57 S56 Tl3 153.5(5) . 4_565 ?
S56 C57 H57A 109.5 . . ?
S56 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
S56 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C62 C61 C66 117.6(16) . . ?
C62 C61 C52 118.5(16) . . ?
C66 C61 C52 123.8(14) . . ?
C61 C62 C63 121.8(19) . . ?
C61 C62 H62 119.1 . . ?
C63 C62 H62 119.1 . . ?
C64 C63 C62 118.4(15) . . ?
C64 C63 H63 120.8 . . ?
C62 C63 H63 120.8 . . ?
C63 C64 C65 124.3(16) . . ?
C63 C64 Cl67 119.9(12) . . ?
C65 C64 Cl67 115.8(15) . . ?
C64 C65 C66 114.1(17) . . ?
C64 C65 H65 123.0 . . ?
C66 C65 H65 123.0 . . ?
C61 C66 C65 123.7(15) . . ?
C61 C66 H66 118.1 . . ?
C65 C66 H66 118.1 . . ?

_refine_diff_density_max         3.776
_refine_diff_density_min         -3.232
_refine_diff_density_rms         0.470

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1534940'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 O S3 Tl'
_chemical_formula_weight         419.69

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'
N N 0.0061 0.0033 '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'
Tl Tl -2.8358 9.6688 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

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

_cell_length_a                   4.1521(4)
_cell_length_b                   8.1183(7)
_cell_length_c                   30.921(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1042.30(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6247
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      29.99

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.674
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    16.051
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'

_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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  'Oxford Diffraction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a

_diffrn_reflns_number            6247
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.639
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3012
_reflns_number_gt                2559
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0829P)²+13.4100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3012
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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_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
Tl1 Tl 0.00726(18) -0.53077(8) -0.71591(2) 0.0248(2) Uani 1 1 d . . . . .
O11 O 0.448(3) -0.5038(17) -0.6472(5) 0.031(3) Uani 1 1 d . . . . .
C12 C 0.569(4) -0.401(3) -0.6233(6) 0.024(4) Uani 1 1 d . . . . .
C13 C 0.675(5) -0.239(3) -0.6360(7) 0.029(4) Uani 1 1 d . . . . .
H13 H 0.777101 -0.177830 -0.614521 0.035 Uiso 1 1 calc R U . . .
C14 C 0.647(4) -0.163(2) -0.6748(6) 0.020(4) Uani 1 1 d . . . . .
S15 S 0.5043(14) -0.2419(5) -0.72316(14) 0.0229(8) Uani 1 1 d . . . . .
S16 S 0.7689(12) 0.0430(6) -0.68263(18) 0.0279(10) Uani 1 1 d . . . . .
C17 C 0.971(7) 0.104(3) -0.6330(7) 0.040(5) Uani 1 1 d . . . . .
H17A H 1.166219 0.041441 -0.629764 0.060 Uiso 1 1 calc R U . . .
H17B H 0.832491 0.083409 -0.608770 0.060 Uiso 1 1 calc R U . . .
H17C H 1.022458 0.219182 -0.634245 0.060 Uiso 1 1 calc R U . . .
C18 C 0.603(4) -0.440(2) -0.5770(5) 0.019(4) Uani 1 1 d . . . . .
C19 C 0.766(5) -0.359(3) -0.5444(6) 0.031(5) Uani 1 1 d . . . . .
H19 H 0.883820 -0.262836 -0.547978 0.037 Uiso 1 1 calc R U . . .
C20 C 0.726(5) -0.447(3) -0.5039(7) 0.036(5) Uani 1 1 d . . . . .
H20 H 0.812459 -0.411207 -0.477690 0.043 Uiso 1 1 calc R U . . .
C21 C 0.550(6) -0.585(3) -0.5085(7) 0.039(5) Uani 1 1 d . . . . .
H21 H 0.499722 -0.654500 -0.485625 0.047 Uiso 1 1 calc R U . . .
S22 S 0.4305(11) -0.6199(7) -0.55913(17) 0.0293(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tl1 O11 2.812(13) . ?
Tl1 S15 3.132(5) . ?
Tl1 S15 3.148(5) 1_455 ?
Tl1 O11 3.157(16) 1_455 ?
Tl1 S15 3.256(5) 3_643 ?
Tl1 S15 3.316(5) 3_543 ?
Tl1 S16 3.327(6) 3_643 ?
Tl1 Tl1 4.1521(4) 1_655 ?
Tl1 Tl1 4.1521(4) 1_455 ?
Tl1 Tl1 4.5745(7) 3_553 ?
Tl1 Tl1 4.5745(7) 3_543 ?
O11 C12 1.22(2) . ?
C12 C13 1.44(3) . ?
C12 C18 1.47(2) . ?
C13 C14 1.35(3) . ?
C13 H13 0.9300 . ?
C14 S15 1.734(19) . ?
C14 S16 1.760(19) . ?
S16 C17 1.82(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.38(3) . ?
C18 S22 1.72(2) . ?
C19 C20 1.45(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.35(4) . ?
C20 H20 0.9300 . ?
C21 S22 1.67(2) . ?
C21 H21 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
O11 Tl1 S15 64.4(3) . . ?
O11 Tl1 S15 115.3(3) . 1_455 ?
S15 Tl1 S15 82.77(10) . 1_455 ?
O11 Tl1 O11 87.9(4) . 1_455 ?
S15 Tl1 O11 118.8(3) . 1_455 ?
S15 Tl1 O11 60.5(3) 1_455 1_455 ?
O11 Tl1 S15 94.2(3) . 3_643 ?
S15 Tl1 S15 86.69(5) . 3_643 ?
S15 Tl1 S15 139.83(7) 1_455 3_643 ?
O11 Tl1 S15 152.2(3) 1_455 3_643 ?
O11 Tl1 S15 152.4(3) . 3_543 ?
S15 Tl1 S15 140.20(7) . 3_543 ?
S15 Tl1 S15 85.39(5) 1_455 3_543 ?
O11 Tl1 S15 87.0(2) 1_455 3_543 ?
S15 Tl1 S15 78.35(9) 3_643 3_543 ?
O11 Tl1 S16 121.2(3) . 3_643 ?
S15 Tl1 S16 67.27(12) . 3_643 ?
S15 Tl1 S16 89.09(12) 1_455 3_643 ?
O11 Tl1 S16 145.9(3) 1_455 3_643 ?
S15 Tl1 S16 51.31(11) 3_643 3_643 ?
S15 Tl1 S16 74.69(12) 3_543 3_643 ?
O11 Tl1 Tl1 49.5(3) . 1_655 ?
S15 Tl1 Tl1 48.78(10) . 1_655 ?
S15 Tl1 Tl1 131.56(9) 1_455 1_655 ?
O11 Tl1 Tl1 137.4(2) 1_455 1_655 ?
S15 Tl1 Tl1 51.47(9) 3_643 1_655 ?
S15 Tl1 Tl1 129.82(9) 3_543 1_655 ?
S16 Tl1 Tl1 73.78(9) 3_643 1_655 ?
O11 Tl1 Tl1 130.5(3) . 1_455 ?
S15 Tl1 Tl1 131.22(10) . 1_455 ?
S15 Tl1 Tl1 48.44(9) 1_455 1_455 ?
O11 Tl1 Tl1 42.6(2) 1_455 1_455 ?
S15 Tl1 Tl1 128.53(9) 3_643 1_455 ?
S15 Tl1 Tl1 50.18(9) 3_543 1_455 ?
S16 Tl1 Tl1 106.22(9) 3_643 1_455 ?
Tl1 Tl1 Tl1 180.0 1_655 1_455 ?
O11 Tl1 Tl1 106.7(3) . 3_553 ?
S15 Tl1 Tl1 46.47(9) . 3_553 ?
S15 Tl1 Tl1 45.37(9) 1_455 3_553 ?
O11 Tl1 Tl1 103.8(3) 1_455 3_553 ?
S15 Tl1 Tl1 102.04(8) 3_643 3_553 ?
S15 Tl1 Tl1 100.85(8) 3_543 3_553 ?
S16 Tl1 Tl1 53.79(9) 3_643 3_553 ?
Tl1 Tl1 Tl1 90.76(2) 1_655 3_553 ?
Tl1 Tl1 Tl1 89.246(19) 1_455 3_553 ?
O11 Tl1 Tl1 115.2(3) . 3_543 ?
S15 Tl1 Tl1 129.80(10) . 3_543 ?
S15 Tl1 Tl1 128.27(9) 1_455 3_543 ?
O11 Tl1 Tl1 111.2(2) 1_455 3_543 ?
S15 Tl1 Tl1 43.48(9) 3_643 3_543 ?
S15 Tl1 Tl1 43.21(8) 3_543 3_543 ?
S16 Tl1 Tl1 74.25(9) 3_643 3_543 ?
Tl1 Tl1 Tl1 90.755(19) 1_655 3_543 ?
Tl1 Tl1 Tl1 89.25(2) 1_455 3_543 ?
Tl1 Tl1 Tl1 125.08(3) 3_553 3_543 ?
C12 O11 Tl1 141.1(14) . . ?
C12 O11 Tl1 98.6(12) . 1_655 ?
Tl1 O11 Tl1 87.9(4) . 1_655 ?
O11 C12 C13 126(2) . . ?
O11 C12 C18 118.8(19) . . ?
C13 C12 C18 115.4(18) . . ?
C14 C13 C12 129(2) . . ?
C14 C13 H13 115.4 . . ?
C12 C13 H13 115.4 . . ?
C13 C14 S15 128.6(16) . . ?
C13 C14 S16 122.0(15) . . ?
S15 C14 S16 109.3(10) . . ?
C14 S15 Tl1 116.2(7) . . ?
C14 S15 Tl1 89.4(6) . 1_655 ?
Tl1 S15 Tl1 82.77(10) . 1_655 ?
C14 S15 Tl1 95.2(7) . 3_653 ?
Tl1 S15 Tl1 147.78(15) . 3_653 ?
Tl1 S15 Tl1 91.16(15) 1_655 3_653 ?
C14 S15 Tl1 121.1(6) . 3_553 ?
Tl1 S15 Tl1 90.33(14) . 3_553 ?
Tl1 S15 Tl1 148.24(15) 1_655 3_553 ?
Tl1 S15 Tl1 78.35(9) 3_653 3_553 ?
C14 S16 C17 105.9(10) . . ?
C14 S16 Tl1 92.3(7) . 3_653 ?
C17 S16 Tl1 135.7(10) . 3_653 ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C12 131.1(19) . . ?
C19 C18 S22 111.9(15) . . ?
C12 C18 S22 116.9(14) . . ?
C18 C19 C20 110(2) . . ?
C18 C19 H19 124.9 . . ?
C20 C19 H19 124.9 . . ?
C21 C20 C19 112.0(19) . . ?
C21 C20 H20 124.0 . . ?
C19 C20 H20 124.0 . . ?
C20 C21 S22 113.9(18) . . ?
C20 C21 H21 123.1 . . ?
S22 C21 H21 123.1 . . ?
C21 S22 C18 91.8(11) . . ?

_refine_diff_density_max         4.494
_refine_diff_density_min         -3.662
_refine_diff_density_rms         0.355

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1534943'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H26 O2 S4 Tl2'
_chemical_formula_weight         1027.55

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'
N N 0.0061 0.0033 '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'
Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1320(7)
_cell_length_b                   11.5849(7)
_cell_length_c                   12.7090(8)
_cell_angle_alpha                82.345(5)
_cell_angle_beta                 78.454(5)
_cell_angle_gamma                79.481(5)
_cell_volume                     1570.87(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11126
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      30.00


_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08


_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    10.545
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'

_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  1.000


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a

_diffrn_reflns_number            11126
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.587
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             8776
_reflns_number_gt                6677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8776
_refine_ls_number_parameters     399
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.001
_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_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
Tl1 Tl 0.87893(3) 0.54714(2) 0.65033(3) 0.02117(8) Uani 1 1 d . . . . .
Tl2 Tl 0.60814(3) 0.63541(2) 0.50975(3) 0.02373(9) Uani 1 1 d . . . . .
O11 O 0.6454(5) 0.5141(4) 0.7187(4) 0.0228(11) Uani 1 1 d . . . . .
C12 C 0.5934(6) 0.4236(6) 0.7380(6) 0.0174(14) Uani 1 1 d . . . . .
C13 C 0.6101(6) 0.3335(5) 0.6700(6) 0.0125(13) Uani 1 1 d . U . . .
H13 H 0.558756 0.276471 0.691792 0.015 Uiso 1 1 calc R U . . .
C14 C 0.6944(6) 0.3196(5) 0.5739(6) 0.0132(13) Uani 1 1 d . . . . .
S15 S 0.79801(17) 0.40798(15) 0.50760(15) 0.0182(4) Uani 1 1 d . . . . .
S16 S 0.68559(17) 0.19189(15) 0.51518(17) 0.0203(4) Uani 1 1 d . . . . .
C17 C 0.8035(7) 0.1879(6) 0.3960(6) 0.0236(16) Uani 1 1 d . . . . .
H17A H 0.785243 0.256504 0.346983 0.035 Uiso 1 1 calc R U . . .
H17B H 0.805448 0.118219 0.361945 0.035 Uiso 1 1 calc R U . . .
H17C H 0.882762 0.186695 0.415362 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7005(7) 0.3393(6) 0.9310(7) 0.0227(16) Uani 1 1 d . . . . .
H21 H 0.751708 0.360499 0.866636 0.027 Uiso 1 1 calc R U . . .
C22 C 0.7503(8) 0.2915(6) 1.0190(7) 0.0267(18) Uani 1 1 d . . . . .
H22 H 0.836031 0.280903 1.013676 0.032 Uiso 1 1 calc R U . . .
C23 C 0.6785(8) 0.2580(7) 1.1165(7) 0.0297(19) Uani 1 1 d . . . . .
H23 H 0.716073 0.222262 1.174289 0.036 Uiso 1 1 calc R U . . .
C24 C 0.5687(7) 0.3570(6) 0.9375(6) 0.0162(14) Uani 1 1 d . . . . .
C25 C 0.5529(8) 0.2775(6) 1.1271(7) 0.0238(16) Uani 1 1 d . . . . .
H25 H 0.504959 0.258583 1.193846 0.029 Uiso 1 1 calc R U . . .
C26 C 0.4924(7) 0.3264(6) 1.0382(6) 0.0192(15) Uani 1 1 d . . . . .
C27 C 0.3641(7) 0.3439(6) 1.0479(6) 0.0173(14) Uani 1 1 d . . . . .
H27 H 0.315142 0.324260 1.113952 0.021 Uiso 1 1 calc R U . . .
C28 C 0.3076(6) 0.3909(6) 0.9589(6) 0.0173(14) Uani 1 1 d . . . . .
C29 C 0.1757(7) 0.4044(7) 0.9662(7) 0.0271(18) Uani 1 1 d . . . . .
H29 H 0.126309 0.380855 1.030847 0.033 Uiso 1 1 calc R U . . .
C30 C 0.1223(8) 0.4509(7) 0.8802(8) 0.0296(19) Uani 1 1 d . . . . .
H30 H 0.036552 0.459192 0.886754 0.036 Uiso 1 1 calc R U . . .
C31 C 0.1945(7) 0.4873(6) 0.7801(7) 0.0206(16) Uani 1 1 d . . . . .
H31 H 0.156066 0.520810 0.722170 0.025 Uiso 1 1 calc R U . . .
C32 C 0.3199(7) 0.4729(6) 0.7694(7) 0.0193(15) Uani 1 1 d . . . . .
H32 H 0.366949 0.496330 0.703538 0.023 Uiso 1 1 calc R U . . .
C33 C 0.3807(7) 0.4226(5) 0.8569(6) 0.0164(14) Uani 1 1 d . . . . .
C34 C 0.5125(7) 0.4031(5) 0.8471(6) 0.0148(14) Uani 1 1 d . . . . .
O41 O 0.6889(5) 0.7467(4) 0.6364(5) 0.0241(12) Uani 1 1 d . . . . .
C42 C 0.7391(6) 0.8377(5) 0.6270(6) 0.0139(13) Uani 1 1 d . . . . .
C43 C 0.8320(6) 0.8721(5) 0.5429(6) 0.0135(13) Uani 1 1 d . U . . .
H43 H 0.857259 0.943139 0.547488 0.016 Uiso 1 1 calc R U . . .
C44 C 0.8916(6) 0.8126(6) 0.4525(6) 0.0151(14) Uani 1 1 d . . . . .
S45 S 0.87299(17) 0.67867(14) 0.42323(16) 0.0189(4) Uani 1 1 d . . . . .
S46 S 0.99673(18) 0.89281(15) 0.36611(17) 0.0237(4) Uani 1 1 d . . . . .
C47 C 1.0682(7) 0.8031(6) 0.2592(7) 0.0256(18) Uani 1 1 d . . . . .
H47A H 1.116760 0.732973 0.287551 0.038 Uiso 1 1 calc R U . . .
H47B H 1.121167 0.846447 0.205418 0.038 Uiso 1 1 calc R U . . .
H47C H 1.005193 0.781853 0.227312 0.038 Uiso 1 1 calc R U . . .
C51 C 0.8954(6) 0.8391(6) 0.7834(6) 0.0187(15) Uani 1 1 d . . . . .
H51 H 0.925324 0.795786 0.724443 0.022 Uiso 1 1 calc R U . . .
C52 C 0.9673(7) 0.8345(7) 0.8599(7) 0.0244(17) Uani 1 1 d . . . . .
H52 H 1.045175 0.787539 0.852562 0.029 Uiso 1 1 calc R U . . .
C53 C 0.9249(8) 0.8997(7) 0.9496(7) 0.0278(18) Uani 1 1 d . . . . .
H53 H 0.975021 0.895146 1.000885 0.033 Uiso 1 1 calc R U . . .
C54 C 0.8130(8) 0.9684(7) 0.9623(7) 0.0249(17) Uani 1 1 d . . . . .
H54 H 0.786570 1.011279 1.021886 0.030 Uiso 1 1 calc R U . . .
C55 C 0.7333(7) 0.9763(6) 0.8839(6) 0.0174(14) Uani 1 1 d . . . . .
C56 C 0.6162(7) 1.0445(6) 0.8967(6) 0.0212(16) Uani 1 1 d . . . . .
H56 H 0.589003 1.088007 0.955887 0.025 Uiso 1 1 calc R U . . .
C57 C 0.5386(7) 1.0488(6) 0.8224(6) 0.0176(15) Uani 1 1 d . . . . .
C58 C 0.4174(7) 1.1202(6) 0.8342(7) 0.0211(15) Uani 1 1 d . U . . .
H58 H 0.390205 1.163605 0.893404 0.025 Uiso 1 1 calc R U . . .
C59 C 0.3424(8) 1.1259(7) 0.7622(7) 0.0283(18) Uani 1 1 d . . . . .
H59 H 0.264957 1.173586 0.771081 0.034 Uiso 1 1 calc R U . . .
C60 C 0.3830(7) 1.0583(6) 0.6724(8) 0.0270(18) Uani 1 1 d . . . . .
H60 H 0.330839 1.061770 0.622916 0.032 Uiso 1 1 calc R U . . .
C61 C 0.4969(7) 0.9883(6) 0.6572(7) 0.0206(15) Uani 1 1 d . . . . .
H61 H 0.521531 0.944942 0.597842 0.025 Uiso 1 1 calc R U . . .
C62 C 0.5776(6) 0.9818(5) 0.7321(6) 0.0141(13) Uani 1 1 d . . . . .
C63 C 0.6988(6) 0.9134(5) 0.7169(6) 0.0129(13) Uani 1 1 d . . . . .
C64 C 0.7745(7) 0.9100(6) 0.7929(6) 0.0178(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tl1 O11 2.651(5) . ?
Tl1 O41 2.848(5) . ?
Tl1 S15 2.9435(18) . ?
Tl1 S45 3.086(2) . ?
Tl1 S45 3.5106(18) 2_766 ?
Tl1 Tl2 3.7240(4) . ?
Tl1 Tl1 4.3559(7) 2_766 ?
Tl2 O41 2.572(5) . ?
Tl2 O11 2.904(6) . ?
Tl2 S45 3.0410(18) . ?
Tl2 S15 3.0614(19) . ?
Tl2 S16 3.5570(19) 2_666 ?
Tl2 Tl2 4.3480(6) 2_666 ?
O11 C12 1.261(8) . ?
C12 C13 1.406(9) . ?
C12 C34 1.510(10) . ?
C13 C14 1.392(10) . ?
C13 H13 0.9300 . ?
C14 S15 1.703(6) . ?
C14 S16 1.770(6) . ?
S16 C17 1.794(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 C22 1.355(11) . ?
C21 C24 1.431(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(12) . ?
C22 H22 0.9300 . ?
C23 C25 1.357(12) . ?
C23 H23 0.9300 . ?
C24 C34 1.414(10) . ?
C24 C26 1.428(10) . ?
C25 C26 1.430(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.389(10) . ?
C27 C28 1.402(10) . ?
C27 H27 0.9300 . ?
C28 C33 1.428(10) . ?
C28 C29 1.433(10) . ?
C29 C30 1.350(12) . ?
C29 H29 0.9300 . ?
C30 C31 1.419(12) . ?
C30 H30 0.9300 . ?
C31 C32 1.356(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.421(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.426(10) . ?
O41 C42 1.261(7) . ?
C42 C43 1.402(9) . ?
C42 C63 1.482(9) . ?
C43 C44 1.405(10) . ?
C43 H43 0.9300 . ?
C44 S45 1.700(6) . ?
C44 S46 1.746(7) . ?
S46 C47 1.789(8) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C51 C52 1.367(10) . ?
C51 C64 1.435(10) . ?
C51 H51 0.9300 . ?
C52 C53 1.406(12) . ?
C52 H52 0.9300 . ?
C53 C54 1.343(12) . ?
C53 H53 0.9300 . ?
C54 C55 1.444(11) . ?
C54 H54 0.9300 . ?
C55 C56 1.388(10) . ?
C55 C64 1.425(10) . ?
C56 C57 1.393(11) . ?
C56 H56 0.9300 . ?
C57 C62 1.421(10) . ?
C57 C58 1.439(10) . ?
C58 C59 1.344(12) . ?
C58 H58 0.9300 . ?
C59 C60 1.423(12) . ?
C59 H59 0.9300 . ?
C60 C61 1.368(10) . ?
C60 H60 0.9300 . ?
C61 C62 1.420(10) . ?
C61 H61 0.9300 . ?
C62 C63 1.426(9) . ?
C63 C64 1.396(10) . ?

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
O11 Tl1 O41 62.29(14) . . ?
O11 Tl1 S15 68.15(12) . . ?
O41 Tl1 S15 96.70(11) . . ?
O11 Tl1 S45 102.89(13) . . ?
O41 Tl1 S45 63.95(12) . . ?
S15 Tl1 S45 68.00(5) . . ?
O11 Tl1 S45 124.18(11) . 2_766 ?
O41 Tl1 S45 161.45(12) . 2_766 ?
S15 Tl1 S45 72.88(5) . 2_766 ?
S45 Tl1 S45 97.62(4) . 2_766 ?
O11 Tl1 Tl2 50.87(12) . . ?
O41 Tl1 Tl2 43.59(10) . . ?
S15 Tl1 Tl2 53.11(4) . . ?
S45 Tl1 Tl2 52.02(3) . . ?
S45 Tl1 Tl2 123.96(3) 2_766 . ?
O11 Tl1 Tl1 127.65(11) . 2_766 ?
O41 Tl1 Tl1 116.93(11) . 2_766 ?
S15 Tl1 Tl1 59.82(4) . 2_766 ?
S45 Tl1 Tl1 53.02(3) . 2_766 ?
S45 Tl1 Tl1 44.61(3) 2_766 2_766 ?
Tl2 Tl1 Tl1 90.811(12) . 2_766 ?
O41 Tl2 O11 62.35(15) . . ?
O41 Tl2 S45 67.66(13) . . ?
O11 Tl2 S45 98.21(11) . . ?
O41 Tl2 S15 100.02(12) . . ?
O11 Tl2 S15 63.55(11) . . ?
S45 Tl2 S15 67.12(4) . . ?
O41 Tl2 S16 102.92(13) . 2_666 ?
O11 Tl2 S16 119.06(11) . 2_666 ?
S45 Tl2 S16 132.39(5) . 2_666 ?
S15 Tl2 S16 154.65(4) . 2_666 ?
O41 Tl2 Tl1 49.76(12) . . ?
O11 Tl2 Tl1 45.08(10) . . ?
S45 Tl2 Tl1 53.13(4) . . ?
S15 Tl2 Tl1 50.26(3) . . ?
S16 Tl2 Tl1 151.11(3) 2_666 . ?
O41 Tl2 Tl2 145.58(12) . 2_666 ?
O11 Tl2 Tl2 86.51(9) . 2_666 ?
S45 Tl2 Tl2 135.81(3) . 2_666 ?
S15 Tl2 Tl2 76.36(3) . 2_666 ?
S16 Tl2 Tl2 78.63(3) 2_666 2_666 ?
Tl1 Tl2 Tl2 117.564(12) . 2_666 ?
C12 O11 Tl1 133.3(5) . . ?
C12 O11 Tl2 109.9(5) . . ?
Tl1 O11 Tl2 84.05(14) . . ?
O11 C12 C13 126.2(7) . . ?
O11 C12 C34 118.3(6) . . ?
C13 C12 C34 115.4(5) . . ?
C14 C13 C12 127.6(6) . . ?
C14 C13 H13 116.2 . . ?
C12 C13 H13 116.2 . . ?
C13 C14 S15 129.3(5) . . ?
C13 C14 S16 112.6(5) . . ?
S15 C14 S16 118.1(4) . . ?
C14 S15 Tl1 113.5(3) . . ?
C14 S15 Tl2 95.1(2) . . ?
Tl1 S15 Tl2 76.63(4) . . ?
C14 S16 C17 105.6(3) . . ?
C14 S16 Tl2 79.0(2) . 2_666 ?
C17 S16 Tl2 116.9(3) . 2_666 ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 C24 119.7(8) . . ?
C22 C21 H21 120.2 . . ?
C24 C21 H21 120.2 . . ?
C21 C22 C23 122.6(8) . . ?
C21 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
C25 C23 C22 119.5(8) . . ?
C25 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C34 C24 C26 119.4(7) . . ?
C34 C24 C21 121.8(7) . . ?
C26 C24 C21 118.8(7) . . ?
C23 C25 C26 121.7(8) . . ?
C23 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C27 C26 C24 120.3(7) . . ?
C27 C26 C25 122.0(7) . . ?
C24 C26 C25 117.7(7) . . ?
C26 C27 C28 120.6(7) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C33 120.7(7) . . ?
C27 C28 C29 121.3(7) . . ?
C33 C28 C29 117.9(7) . . ?
C30 C29 C28 120.7(8) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 121.4(8) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C32 C31 C30 119.6(8) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 121.3(7) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C32 C33 C34 122.5(7) . . ?
C32 C33 C28 119.1(7) . . ?
C34 C33 C28 118.4(7) . . ?
C24 C34 C33 120.5(7) . . ?
C24 C34 C12 119.4(6) . . ?
C33 C34 C12 120.0(6) . . ?
C42 O41 Tl2 136.1(5) . . ?
C42 O41 Tl1 107.4(4) . . ?
Tl2 O41 Tl1 86.65(14) . . ?
O41 C42 C43 127.0(7) . . ?
O41 C42 C63 116.2(6) . . ?
C43 C42 C63 116.7(5) . . ?
C42 C43 C44 128.1(6) . . ?
C42 C43 H43 115.9 . . ?
C44 C43 H43 115.9 . . ?
C43 C44 S45 127.8(5) . . ?
C43 C44 S46 111.7(4) . . ?
S45 C44 S46 120.5(4) . . ?
C44 S45 Tl2 110.5(2) . . ?
C44 S45 Tl1 97.4(3) . . ?
Tl2 S45 Tl1 74.85(4) . . ?
C44 S45 Tl1 123.6(2) . 2_766 ?
Tl2 S45 Tl1 123.32(5) . 2_766 ?
Tl1 S45 Tl1 82.38(4) . 2_766 ?
C44 S46 C47 106.0(3) . . ?
S46 C47 H47A 109.5 . . ?
S46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
S46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C52 C51 C64 120.9(7) . . ?
C52 C51 H51 119.5 . . ?
C64 C51 H51 119.5 . . ?
C51 C52 C53 120.8(8) . . ?
C51 C52 H52 119.6 . . ?
C53 C52 H52 119.6 . . ?
C54 C53 C52 120.9(8) . . ?
C54 C53 H53 119.5 . . ?
C52 C53 H53 119.5 . . ?
C53 C54 C55 120.5(7) . . ?
C53 C54 H54 119.8 . . ?
C55 C54 H54 119.8 . . ?
C56 C55 C64 119.2(7) . . ?
C56 C55 C54 121.4(7) . . ?
C64 C55 C54 119.4(7) . . ?
C55 C56 C57 121.0(7) . . ?
C55 C56 H56 119.5 . . ?
C57 C56 H56 119.5 . . ?
C56 C57 C62 120.4(7) . . ?
C56 C57 C58 121.5(7) . . ?
C62 C57 C58 118.1(7) . . ?
C59 C58 C57 121.9(7) . . ?
C59 C58 H58 119.0 . . ?
C57 C58 H58 119.0 . . ?
C58 C59 C60 119.2(8) . . ?
C58 C59 H59 120.4 . . ?
C60 C59 H59 120.4 . . ?
C61 C60 C59 121.5(8) . . ?
C61 C60 H60 119.3 . . ?
C59 C60 H60 119.3 . . ?
C60 C61 C62 120.0(7) . . ?
C60 C61 H61 120.0 . . ?
C62 C61 H61 120.0 . . ?
C61 C62 C57 119.3(7) . . ?
C61 C62 C63 121.7(7) . . ?
C57 C62 C63 119.0(6) . . ?
C64 C63 C62 119.4(6) . . ?
C64 C63 C42 120.3(6) . . ?
C62 C63 C42 120.0(6) . . ?
C63 C64 C55 120.9(7) . . ?
C63 C64 C51 121.6(7) . . ?
C55 C64 C51 117.5(7) . . ?

_refine_diff_density_max         2.839
_refine_diff_density_min         -3.253
_refine_diff_density_rms         0.276

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1842767'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 N O S2 Tl'
_chemical_formula_weight         414.65

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'
N N 0.0061 0.0033 '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'
Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

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

_cell_length_a                   11.0854(5)
_cell_length_b                   26.1784(12)
_cell_length_c                   7.1879(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2085.91(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    28722
_cell_measurement_theta_min      2.971
_cell_measurement_theta_max      27.491

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.641
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    15.849
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4217
_exptl_absorpt_correction_T_max  0.7291
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest SCM Diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28722
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2402
_reflns_number_gt                1977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+3.0047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2402
_refine_ls_number_parameters     128
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0545
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.002
_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_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
Tl1 Tl 0.40511(2) 0.31995(2) 0.52041(2) 0.01466(7) Uani 1 1 d . . . . .
O11 O 0.2564(3) 0.40264(13) 0.5388(4) 0.0181(7) Uani 1 1 d . . . . .
C12 C 0.1532(4) 0.41375(18) 0.5922(6) 0.0137(9) Uani 1 1 d . . . . .
C13 C 0.0527(4) 0.37847(18) 0.6010(6) 0.0145(10) Uani 1 1 d . . . . .
H13 H -0.017329 0.390125 0.664438 0.017 Uiso 1 1 calc R U . . .
C14 C 0.0473(4) 0.33038(18) 0.5284(6) 0.0130(9) Uani 1 1 d . . . . .
S15 S 0.15923(10) 0.29544(5) 0.41937(16) 0.0156(2) Uani 1 1 d . . . . .
S16 S -0.08514(10) 0.29398(5) 0.53310(17) 0.0171(2) Uani 1 1 d . . . . .
C17 C -0.1956(4) 0.33226(19) 0.6521(7) 0.0207(11) Uani 1 1 d . . . . .
H17A H -0.167187 0.339756 0.778317 0.031 Uiso 1 1 calc R U . . .
H17B H -0.272045 0.313562 0.658663 0.031 Uiso 1 1 calc R U . . .
H17C H -0.207659 0.364316 0.584220 0.031 Uiso 1 1 calc R U . . .
C21 C 0.1297(4) 0.46823(18) 0.6465(6) 0.0120(9) Uani 1 1 d . . . . .
C22 C 0.2149(4) 0.50473(17) 0.5957(6) 0.0138(9) Uani 1 1 d . . . . .
H22 H 0.283146 0.493459 0.527097 0.017 Uiso 1 1 calc R U . . .
N23 N 0.2077(3) 0.55458(14) 0.6363(5) 0.0149(8) Uani 1 1 d . U . . .
C24 C 0.1098(4) 0.56959(19) 0.7293(6) 0.0147(10) Uani 1 1 d . . . . .
H24 H 0.102577 0.604748 0.759994 0.018 Uiso 1 1 calc R U . . .
C25 C 0.0177(4) 0.53675(19) 0.7840(6) 0.0142(9) Uani 1 1 d . . . . .
H25 H -0.050976 0.549330 0.848473 0.017 Uiso 1 1 calc R U . . .
C26 C 0.0284(4) 0.48554(18) 0.7424(6) 0.0138(9) Uani 1 1 d . . . . .
H26 H -0.032894 0.462221 0.778882 0.017 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
Tl1 O11 2.724(3) . ?
Tl1 S15 2.8929(12) . ?
Tl1 S15 3.0240(12) 7_656 ?
Tl1 S15 3.1875(12) 2 ?
Tl1 S16 3.5897(12) 2 ?
O11 C12 1.241(5) . ?
C12 C13 1.449(6) . ?
C12 C21 1.501(6) . ?
C13 C14 1.364(6) . ?
C14 S15 1.729(5) . ?
C14 S16 1.751(5) . ?
S16 C17 1.799(5) . ?
C21 C26 1.394(6) . ?
C21 C22 1.392(6) . ?
C22 N23 1.340(6) . ?
N23 C24 1.334(5) . ?
C24 C25 1.392(6) . ?
C25 C26 1.379(7) . ?

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
O11 Tl1 S15 67.55(7) . . ?
O11 Tl1 S15 88.85(7) . 7_656 ?
S15 Tl1 S15 88.21(2) . 7_656 ?
O11 Tl1 S15 128.95(7) . 2 ?
S15 Tl1 S15 61.43(4) . 2 ?
S15 Tl1 S15 87.83(3) 7_656 2 ?
O11 Tl1 S16 174.51(7) . 2 ?
S15 Tl1 S16 110.24(3) . 2 ?
S15 Tl1 S16 86.03(3) 7_656 2 ?
S15 Tl1 S16 48.92(3) 2 2 ?
C12 O11 Tl1 139.4(3) . . ?
O11 C12 C13 125.0(4) . . ?
O11 C12 C21 117.6(4) . . ?
C13 C12 C21 117.4(4) . . ?
C14 C13 C12 127.2(4) . . ?
C13 C14 S15 129.1(4) . . ?
C13 C14 S16 122.1(4) . . ?
S15 C14 S16 108.8(3) . . ?
C14 S15 Tl1 116.41(16) . . ?
C14 S15 Tl1 98.54(15) . 7_655 ?
Tl1 S15 Tl1 114.41(4) . 7_655 ?
C14 S15 Tl1 103.74(16) . 2 ?
Tl1 S15 Tl1 111.33(4) . 2 ?
Tl1 S15 Tl1 111.37(4) 7_655 2 ?
C14 S16 C17 106.1(2) . . ?
C14 S16 Tl1 89.17(16) . 2 ?
C17 S16 Tl1 148.59(17) . 2 ?
C26 C21 C22 116.9(4) . . ?
C26 C21 C12 125.2(4) . . ?
C22 C21 C12 117.8(4) . . ?
N23 C22 C21 124.8(4) . . ?
C24 N23 C22 116.4(4) . . ?
N23 C24 C25 123.8(5) . . ?
C26 C25 C24 118.4(4) . . ?
C25 C26 C21 119.5(4) . . ?

_refine_diff_density_max         0.782
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.181

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1534941'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 F2 O2 S4 Tl2'
_chemical_formula_weight         863.31

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'
N N 0.0061 0.0033 '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'
Tl Tl -2.8358 9.6688 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   17.9716(9)
_cell_length_b                   6.0317(2)
_cell_length_c                   22.2375(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.937(6)
_cell_angle_gamma                90
_cell_volume                     2235.99(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14165
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      30.00

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.565
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    14.801
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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       'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a

_diffrn_reflns_number            14165
_diffrn_reflns_av_unetI/netI     0.1217
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.454
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6452
_reflns_number_gt                4715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-97, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1439P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6452
_refine_ls_number_parameters     273
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2463
_refine_ls_wR_factor_gt          0.2164
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_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_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
Tl1 Tl 0.49792(4) 0.48228(9) -0.17337(2) 0.02403(19) Uani 1 1 d . . . . .
Tl2 Tl 0.60048(3) 0.82260(8) -0.00264(2) 0.02074(18) Uani 1 1 d . . . . .
O11 O 0.6388(6) 0.5468(16) -0.0842(4) 0.021(2) Uani 1 1 d . . . . .
C12 C 0.7065(7) 0.5781(18) -0.0905(6) 0.012(2) Uani 1 1 d . . . . .
C13 C 0.7198(8) 0.749(2) -0.1295(6) 0.016(2) Uani 1 1 d . . . . .
H21 H 0.769114 0.751711 -0.134177 0.019 Uiso 1 1 calc R U . . .
C14 C 0.6634(8) 0.913(2) -0.1616(6) 0.017(2) Uani 1 1 d . . . . .
S15 S 0.5673(2) 0.9487(6) -0.16714(17) 0.0243(7) Uani 1 1 d . . . . .
S16 S 0.6901(2) 1.1279(6) -0.20424(16) 0.0215(7) Uani 1 1 d . . . . .
C17 C 0.7928(9) 1.090(3) -0.1916(7) 0.028(3) Uani 1 1 d . . . . .
H25A H 0.824723 1.102371 -0.146240 0.043 Uiso 1 1 calc R U . . .
H25B H 0.809045 1.200703 -0.215163 0.043 Uiso 1 1 calc R U . . .
H25C H 0.800152 0.945243 -0.206707 0.043 Uiso 1 1 calc R U . . .
C21 C 0.7737(7) 0.430(2) -0.0563(6) 0.012(2) Uani 1 1 d . U . . .
C22 C 0.7573(10) 0.234(3) -0.0287(6) 0.026(3) Uani 1 1 d . . . . .
H22 H 0.704648 0.207705 -0.032754 0.031 Uiso 1 1 calc R U . . .
C23 C 0.8133(9) 0.082(2) 0.0033(6) 0.020(3) Uani 1 1 d . . . . .
H23 H 0.799767 -0.046406 0.020119 0.024 Uiso 1 1 calc R U . . .
C24 C 0.8916(11) 0.125(3) 0.0099(7) 0.031(4) Uani 1 1 d . . . . .
F24 F 0.9506(6) -0.0264(13) 0.0428(5) 0.030(2) Uani 1 1 d . . . . .
C25 C 0.9132(10) 0.310(2) -0.0157(7) 0.026(3) Uani 1 1 d . . . . .
H25 H 0.966177 0.332456 -0.011205 0.031 Uiso 1 1 calc R U . . .
C26 C 0.8550(8) 0.459(2) -0.0480(7) 0.021(3) Uani 1 1 d . . . . .
H26 H 0.869377 0.585590 -0.065194 0.025 Uiso 1 1 calc R U . . .
O41 O 0.7436(7) 0.6169(15) 0.0817(5) 0.028(2) Uani 1 1 d . . . . .
C42 C 0.7769(9) 0.451(2) 0.1152(6) 0.016(2) Uani 1 1 d . . . . .
C43 C 0.7295(9) 0.278(2) 0.1311(6) 0.019(3) Uani 1 1 d . . . . .
H43 H 0.759778 0.166623 0.158244 0.023 Uiso 1 1 calc R U . . .
C44 C 0.6491(9) 0.254(2) 0.1128(6) 0.018(3) Uani 1 1 d . . . . .
S45 S 0.5726(3) 0.4093(6) 0.06081(18) 0.0278(8) Uani 1 1 d . . . . .
S46 S 0.6089(2) 0.0298(5) 0.14229(15) 0.0189(7) Uani 1 1 d . . . . .
C47 C 0.6931(10) -0.130(2) 0.1952(6) 0.025(3) Uani 1 1 d . . . . .
H47A H 0.721869 -0.191688 0.170463 0.037 Uiso 1 1 calc R U . . .
H47B H 0.673967 -0.247144 0.214772 0.037 Uiso 1 1 calc R U . . .
H47C H 0.728178 -0.035007 0.228415 0.037 Uiso 1 1 calc R U . . .
C51 C 0.8662(9) 0.425(2) 0.1403(6) 0.019(3) Uani 1 1 d . . . . .
C52 C 0.9079(9) 0.240(2) 0.1709(7) 0.024(3) Uani 1 1 d . . . . .
H52 H 0.880267 0.119142 0.178038 0.029 Uiso 1 1 calc R U . . .
C53 C 0.9899(9) 0.232(2) 0.1910(7) 0.027(3) Uani 1 1 d . . . . .
H53 H 1.017807 0.108937 0.213175 0.032 Uiso 1 1 calc R U . . .
C54 C 1.0302(11) 0.405(3) 0.1785(8) 0.029(3) Uani 1 1 d . . . . .
F54 F 1.1133(6) 0.4004(16) 0.1998(5) 0.036(2) Uani 1 1 d . . . . .
C55 C 0.9911(11) 0.595(3) 0.1483(8) 0.031(3) Uani 1 1 d . . . . .
H55 H 1.019704 0.713836 0.140878 0.037 Uiso 1 1 calc R U . . .
C56 C 0.9078(9) 0.607(2) 0.1290(7) 0.024(3) Uani 1 1 d . . . . .
H56 H 0.880171 0.733555 0.108966 0.029 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
Tl1 O11 2.596(10) . ?
Tl1 S15 3.059(4) . ?
Tl1 S45 3.266(4) 3_665 ?
Tl1 S15 3.300(4) 2_644 ?
Tl1 S15 3.436(3) 1_545 ?
Tl1 S16 3.567(4) 2_644 ?
Tl1 S46 3.717(4) 3_665 ?
Tl1 Tl2 4.0983(7) . ?
Tl1 Tl1 4.5723(8) 2_654 ?
Tl1 Tl1 4.5723(8) 2_644 ?
Tl2 O11 2.732(9) . ?
Tl2 O41 2.840(12) . ?
Tl2 S45 2.998(3) . ?
Tl2 S45 3.209(4) 3_665 ?
Tl2 S46 3.407(3) 1_565 ?
Tl2 S15 3.562(3) . ?
Tl2 Tl2 4.2372(11) 3_675 ?
O11 C12 1.290(16) . ?
C12 C13 1.424(16) . ?
C12 C21 1.468(17) . ?
C13 C14 1.408(18) . ?
C13 H21 0.9300 . ?
C14 S15 1.698(14) . ?
C14 S16 1.773(14) . ?
S16 C17 1.775(17) . ?
C17 H25A 0.9600 . ?
C17 H25B 0.9600 . ?
C17 H25C 0.9600 . ?
C21 C22 1.412(19) . ?
C21 C26 1.415(18) . ?
C22 C23 1.35(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.38(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.37(2) . ?
C24 F24 1.383(17) . ?
C25 C26 1.36(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
O41 C42 1.258(16) . ?
C42 C43 1.471(17) . ?
C42 C51 1.50(2) . ?
C43 C44 1.356(19) . ?
C43 H43 0.9300 . ?
C44 S45 1.707(13) . ?
C44 S46 1.771(14) . ?
S46 C47 1.808(15) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C51 C52 1.374(19) . ?
C51 C56 1.399(18) . ?
C52 C53 1.37(2) . ?
C52 H52 0.9300 . ?
C53 C54 1.36(2) . ?
C53 H53 0.9300 . ?
C54 C55 1.38(2) . ?
C54 F54 1.389(19) . ?
C55 C56 1.40(2) . ?
C55 H55 0.9300 . ?
C56 H56 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
O11 Tl1 S15 64.1(2) . . ?
O11 Tl1 S45 86.1(2) . 3_665 ?
S15 Tl1 S45 92.83(9) . 3_665 ?
O11 Tl1 S15 133.1(2) . 2_644 ?
S15 Tl1 S15 94.60(9) . 2_644 ?
S45 Tl1 S15 138.79(10) 3_665 2_644 ?
O11 Tl1 S15 82.8(2) . 1_545 ?
S15 Tl1 S15 136.39(13) . 1_545 ?
S45 Tl1 S15 113.29(8) 3_665 1_545 ?
S15 Tl1 S15 87.92(10) 2_644 1_545 ?
O11 Tl1 S16 157.1(2) . 2_644 ?
S15 Tl1 S16 93.55(9) . 2_644 ?
S45 Tl1 S16 90.42(9) 3_665 2_644 ?
S15 Tl1 S16 48.72(9) 2_644 2_644 ?
S15 Tl1 S16 119.17(9) 1_545 2_644 ?
O11 Tl1 S46 99.4(2) . 3_665 ?
S15 Tl1 S46 59.58(9) . 3_665 ?
S45 Tl1 S46 47.45(8) 3_665 3_665 ?
S15 Tl1 S46 104.34(9) 2_644 3_665 ?
S15 Tl1 S46 159.89(8) 1_545 3_665 ?
S16 Tl1 S46 62.55(7) 2_644 3_665 ?
O11 Tl1 Tl2 40.9(2) . . ?
S15 Tl1 Tl2 57.51(7) . . ?
S45 Tl1 Tl2 50.11(7) 3_665 . ?
S15 Tl1 Tl2 151.97(6) 2_644 . ?
S15 Tl1 Tl2 113.64(7) 1_545 . ?
S16 Tl1 Tl2 123.60(5) 2_644 . ?
S46 Tl1 Tl2 61.05(5) 3_665 . ?
O11 Tl1 Tl1 100.8(2) . 2_654 ?
S15 Tl1 Tl1 46.16(7) . 2_654 ?
S45 Tl1 Tl1 123.93(6) 3_665 2_654 ?
S15 Tl1 Tl1 48.51(6) 2_644 2_654 ?
S15 Tl1 Tl1 122.77(6) 1_545 2_654 ?
S16 Tl1 Tl1 62.84(6) 2_644 2_654 ?
S46 Tl1 Tl1 76.69(5) 3_665 2_654 ?
Tl2 Tl1 Tl1 103.487(12) . 2_654 ?
O11 Tl1 Tl1 112.7(2) . 2_644 ?
S15 Tl1 Tl1 121.36(7) . 2_644 ?
S45 Tl1 Tl1 145.32(7) 3_665 2_644 ?
S15 Tl1 Tl1 41.97(7) 2_644 2_644 ?
S15 Tl1 Tl1 46.01(6) 1_545 2_644 ?
S16 Tl1 Tl1 82.43(5) 2_644 2_644 ?
S46 Tl1 Tl1 144.51(6) 3_665 2_644 ?
Tl2 Tl1 Tl1 153.37(2) . 2_644 ?
Tl1 Tl1 Tl1 82.537(17) 2_654 2_644 ?
O11 Tl2 O41 77.4(3) . . ?
O11 Tl2 S45 86.2(2) . . ?
O41 Tl2 S45 66.1(2) . . ?
O11 Tl2 S45 85.0(2) . 3_665 ?
O41 Tl2 S45 125.3(2) . 3_665 ?
S45 Tl2 S45 61.30(12) . 3_665 ?
O11 Tl2 S46 156.7(2) . 1_565 ?
O41 Tl2 S46 80.0(2) . 1_565 ?
S45 Tl2 S46 79.40(9) . 1_565 ?
S45 Tl2 S46 103.60(9) 3_665 1_565 ?
O11 Tl2 S15 55.6(2) . . ?
O41 Tl2 S15 122.3(2) . . ?
S45 Tl2 S15 131.89(10) . . ?
S45 Tl2 S15 85.06(9) 3_665 . ?
S46 Tl2 S15 145.53(8) 1_565 . ?
O11 Tl2 Tl1 38.5(2) . . ?
O41 Tl2 Tl1 112.07(19) . . ?
S45 Tl2 Tl1 85.59(8) . . ?
S45 Tl2 Tl1 51.36(7) 3_665 . ?
S46 Tl2 Tl1 154.93(6) 1_565 . ?
S15 Tl2 Tl1 46.43(6) . . ?
O11 Tl2 Tl2 139.0(2) . 3_675 ?
O41 Tl2 Tl2 140.65(19) . 3_675 ?
S45 Tl2 Tl2 96.48(8) . 3_675 ?
S45 Tl2 Tl2 61.55(8) 3_665 3_675 ?
S46 Tl2 Tl2 61.69(7) 1_565 3_675 ?
S15 Tl2 Tl2 95.93(6) . 3_675 ?
Tl1 Tl2 Tl2 100.70(2) . 3_675 ?
C12 O11 Tl1 129.0(7) . . ?
C12 O11 Tl2 117.7(7) . . ?
Tl1 O11 Tl2 100.5(3) . . ?
O11 C12 C13 123.5(11) . . ?
O11 C12 C21 118.8(10) . . ?
C13 C12 C21 117.6(11) . . ?
C14 C13 C12 124.5(12) . . ?
C14 C13 H21 117.8 . . ?
C12 C13 H21 117.8 . . ?
C13 C14 S15 130.2(10) . . ?
C13 C14 S16 119.9(10) . . ?
S15 C14 S16 109.9(7) . . ?
C14 S15 Tl1 105.9(5) . . ?
C14 S15 Tl1 91.6(4) . 2_654 ?
Tl1 S15 Tl1 91.87(10) . 2_654 ?
C14 S15 Tl1 117.7(5) . 1_565 ?
Tl1 S15 Tl1 136.39(13) . 1_565 ?
Tl1 S15 Tl1 85.48(8) 2_654 1_565 ?
C14 S15 Tl2 97.1(5) . . ?
Tl1 S15 Tl2 76.07(7) . . ?
Tl1 S15 Tl2 166.66(14) 2_654 . ?
Tl1 S15 Tl2 99.24(9) 1_565 . ?
C14 S16 C17 107.1(7) . . ?
C14 S16 Tl1 81.9(4) . 2_654 ?
C17 S16 Tl1 136.1(5) . 2_654 ?
S16 C17 H25A 109.5 . . ?
S16 C17 H25B 109.5 . . ?
H25A C17 H25B 109.5 . . ?
S16 C17 H25C 109.5 . . ?
H25A C17 H25C 109.5 . . ?
H25B C17 H25C 109.5 . . ?
C22 C21 C26 115.0(12) . . ?
C22 C21 C12 118.1(11) . . ?
C26 C21 C12 126.9(11) . . ?
C23 C22 C21 124.1(15) . . ?
C23 C22 H22 117.9 . . ?
C21 C22 H22 117.9 . . ?
C22 C23 C24 117.2(13) . . ?
C22 C23 H23 121.4 . . ?
C24 C23 H23 121.4 . . ?
C25 C24 F24 118.4(16) . . ?
C25 C24 C23 122.9(15) . . ?
F24 C24 C23 118.8(13) . . ?
C26 C25 C24 118.4(15) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C25 C26 C21 122.3(12) . . ?
C25 C26 H26 118.8 . . ?
C21 C26 H26 118.8 . . ?
C42 O41 Tl2 148.4(9) . . ?
O41 C42 C43 121.2(13) . . ?
O41 C42 C51 120.6(12) . . ?
C43 C42 C51 118.2(11) . . ?
C44 C43 C42 130.6(13) . . ?
C44 C43 H43 114.7 . . ?
C42 C43 H43 114.7 . . ?
C43 C44 S45 130.1(10) . . ?
C43 C44 S46 120.4(10) . . ?
S45 C44 S46 109.5(8) . . ?
C44 S45 Tl2 122.7(5) . . ?
C44 S45 Tl2 116.6(5) . 3_665 ?
Tl2 S45 Tl2 118.70(12) . 3_665 ?
C44 S45 Tl1 92.1(4) . 3_665 ?
Tl2 S45 Tl1 112.04(12) . 3_665 ?
Tl2 S45 Tl1 78.53(9) 3_665 3_665 ?
C44 S46 C47 106.9(7) . . ?
C44 S46 Tl2 79.0(4) . 1_545 ?
C47 S46 Tl2 98.7(5) . 1_545 ?
C44 S46 Tl1 76.9(4) . 3_665 ?
C47 S46 Tl1 131.7(5) . 3_665 ?
Tl2 S46 Tl1 128.52(10) 1_545 3_665 ?
S46 C47 H47A 109.5 . . ?
S46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
S46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C52 C51 C56 119.7(14) . . ?
C52 C51 C42 125.4(12) . . ?
C56 C51 C42 114.9(12) . . ?
C53 C52 C51 120.7(14) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C54 C53 C52 119.8(14) . . ?
C54 C53 H53 120.1 . . ?
C52 C53 H53 120.1 . . ?
C53 C54 C55 121.6(16) . . ?
C53 C54 F54 120.1(14) . . ?
C55 C54 F54 118.1(14) . . ?
C54 C55 C56 118.8(15) . . ?
C54 C55 H55 120.6 . . ?
C56 C55 H55 120.6 . . ?
C55 C56 C51 119.3(14) . . ?
C55 C56 H56 120.3 . . ?
C51 C56 H56 120.3 . . ?

_refine_diff_density_max         4.490
_refine_diff_density_min         -4.727
_refine_diff_density_rms         0.592

####################################################################### 
# 
# 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_7b
_database_code_depnum_ccdc_archive 'CCDC 1842768'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Cl O S2 Tl'
_chemical_formula_weight         448.10

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tl Tl -2.8358 9.6688 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_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                   8.2435(6)
_cell_length_b                   36.287(4)
_cell_length_c                   4.0103(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1199.61(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4221
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.481
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    14.003
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            4221
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.339
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1959
_reflns_number_gt                1538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.997

_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.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-2016/6, PLATON, WINGX (Ferrugia, 2012)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+4.6512P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1959
_refine_ls_number_parameters     101
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.003
_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_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
Tl1 Tl 0.72811(8) 0.77924(2) 0.3394(9) 0.0231(3) Uani 1 1 d . . . . .
S15 S 1.0192(6) 0.77444(13) -0.151(4) 0.0185(10) Uani 1 1 d . . . . .
S16 S 1.3125(8) 0.8093(2) -0.371(2) 0.0350(17) Uani 1 1 d D . . . .
O11 O 0.7561(16) 0.8380(4) -0.184(11) 0.029(4) Uani 1 1 d . U . . .
C12 C 0.870(3) 0.8600(6) -0.184(11) 0.032(5) Uani 1 1 d . U . . .
C13 C 1.040(3) 0.8496(6) -0.269(6) 0.033(7) Uani 1 1 d . U . . .
H13 H 1.108714 0.868733 -0.332540 0.039 Uiso 1 1 calc DR U . . .
C14 C 1.105(3) 0.8159(7) -0.263(6) 0.026(6) Uani 1 1 d . U . . .
C17 C 1.379(4) 0.8526(7) -0.548(9) 0.063(11) Uani 1 1 d D U . . .
H17A H 1.352479 0.853226 -0.781126 0.094 Uiso 1 1 calc R U . . .
H17B H 1.494037 0.855062 -0.520618 0.094 Uiso 1 1 calc R U . . .
H17C H 1.325149 0.872597 -0.436256 0.094 Uiso 1 1 calc R U . . .
C21A C 0.855(3) 0.9017(6) -0.161(10) 0.015(2) Uiso 0.45(2) 1 d G U P A 1
C22A C 0.950(3) 0.9279(5) -0.322(10) 0.015(2) Uiso 0.45(2) 1 d G U P A 1
H22A H 1.053001 0.921639 -0.398613 0.018 Uiso 0.45(2) 1 calc DR U P A 1
C23A C 0.891(3) 0.9634(5) -0.368(9) 0.015(2) Uiso 0.45(2) 1 d G U P A 1
H23A H 0.954813 0.980953 -0.475302 0.018 Uiso 0.45(2) 1 calc R U P A 1
C24A C 0.738(3) 0.9728(7) -0.252(9) 0.015(2) Uiso 0.45(2) 1 d G U P A 1
C25A C 0.643(3) 0.9466(9) -0.091(10) 0.015(2) Uiso 0.45(2) 1 d G U P A 1
H25A H 0.540091 0.952801 -0.014456 0.018 Uiso 0.45(2) 1 calc R U P A 1
C26A C 0.702(3) 0.9110(8) -0.046(10) 0.015(2) Uiso 0.45(2) 1 d G U P A 1
H26A H 0.638277 0.893486 0.062237 0.018 Uiso 0.45(2) 1 calc R U P A 1
Cl1 Cl 0.705(3) 1.0219(6) -0.281(6) 0.030(2) Uani 0.45(2) 1 d . . P A 1
C21B C 0.826(3) 0.8999(5) -0.146(8) 0.015(2) Uiso 0.55(2) 1 d G U P A 2
C22B C 0.944(3) 0.9223(7) -0.005(8) 0.015(2) Uiso 0.55(2) 1 d G U P A 2
H22B H 1.040980 0.912077 0.069401 0.018 Uiso 0.55(2) 1 calc R U P A 2
C23B C 0.918(3) 0.9600(7) 0.024(8) 0.015(2) Uiso 0.55(2) 1 d G U P A 2
H23B H 0.997073 0.974996 0.118443 0.018 Uiso 0.55(2) 1 calc R U P A 2
C24B C 0.773(3) 0.9753(5) -0.087(8) 0.015(2) Uiso 0.55(2) 1 d G U P A 2
C25B C 0.655(3) 0.9529(7) -0.228(8) 0.015(2) Uiso 0.55(2) 1 d G U P A 2
H25B H 0.557886 0.963191 -0.302969 0.018 Uiso 0.55(2) 1 calc R U P A 2
C26B C 0.681(3) 0.9152(7) -0.258(7) 0.015(2) Uiso 0.55(2) 1 d G U P A 2
H26B H 0.601791 0.900273 -0.352014 0.018 Uiso 0.55(2) 1 calc R U P A 2
Cl2 Cl 0.712(2) 1.0195(5) 0.009(5) 0.030(2) Uani 0.55(2) 1 d . . 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
Tl1 O11 2.87(3) 1_556 ?
Tl1 O11 3.00(3) . ?
Tl1 S15 3.108(11) . ?
Tl1 S15 3.156(11) 1_556 ?
Tl1 S15 3.261(10) 3_465 ?
Tl1 S15 3.306(11) 3_466 ?
Tl1 S16 3.485(8) 3_466 ?
Tl1 Tl1 4.0103(4) 1_554 ?
Tl1 Tl1 4.6361(7) 3_465 ?
Tl1 Tl1 4.6361(7) 3_565 ?
S15 C14 1.72(2) . ?
S16 C14 1.78(2) . ?
S16 C17 1.812(19) . ?
O11 C12 1.23(2) . ?
C12 C13 1.49(3) . ?
C12 C21B 1.50(3) . ?
C12 C21A 1.52(3) . ?
C13 C14 1.34(3) . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21A C22A 1.3900 . ?
C21A C26A 1.3900 . ?
C22A C23A 1.3900 . ?
C22A H22A 0.9300 . ?
C23A C24A 1.3900 . ?
C23A H23A 0.9300 . ?
C24A C25A 1.3900 . ?
C24A Cl1 1.80(3) . ?
C25A C26A 1.3900 . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
C21B C22B 1.3900 . ?
C21B C26B 1.3900 . ?
C22B C23B 1.3900 . ?
C22B H22B 0.9300 . ?
C23B C24B 1.3900 . ?
C23B H23B 0.9300 . ?
C24B C25B 1.3900 . ?
C24B Cl2 1.72(3) . ?
C25B C26B 1.3900 . ?
C25B H25B 0.9300 . ?
C26B H26B 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
O11 Tl1 O11 86.1(4) 1_556 . ?
O11 Tl1 S15 113.6(4) 1_556 . ?
O11 Tl1 S15 62.5(4) . . ?
O11 Tl1 S15 63.2(5) 1_556 1_556 ?
O11 Tl1 S15 115.7(5) . 1_556 ?
S15 Tl1 S15 79.61(11) . 1_556 ?
O11 Tl1 S15 152.5(3) 1_556 3_465 ?
O11 Tl1 S15 92.5(6) . 3_465 ?
S15 Tl1 S15 89.6(4) . 3_465 ?
S15 Tl1 S15 139.38(7) 1_556 3_465 ?
O11 Tl1 S15 93.9(7) 1_556 3_466 ?
O11 Tl1 S15 153.0(3) . 3_466 ?
S15 Tl1 S15 139.48(7) . 3_466 ?
S15 Tl1 S15 87.9(3) 1_556 3_466 ?
S15 Tl1 S15 75.27(10) 3_465 3_466 ?
O11 Tl1 S16 116.5(7) 1_556 3_466 ?
O11 Tl1 S16 150.8(5) . 3_466 ?
S15 Tl1 S16 90.30(16) . 3_466 ?
S15 Tl1 S16 65.26(15) 1_556 3_466 ?
S15 Tl1 S16 75.9(2) 3_465 3_466 ?
S15 Tl1 S16 49.84(14) 3_466 3_466 ?
O11 Tl1 Tl1 131.7(7) 1_556 1_554 ?
O11 Tl1 Tl1 45.6(6) . 1_554 ?
S15 Tl1 Tl1 50.7(2) . 1_554 ?
S15 Tl1 Tl1 130.3(2) 1_556 1_554 ?
S15 Tl1 Tl1 52.9(2) 3_465 1_554 ?
S15 Tl1 Tl1 128.2(2) 3_466 1_554 ?
S16 Tl1 Tl1 109.48(14) 3_466 1_554 ?
O11 Tl1 Tl1 114.3(3) 1_556 3_465 ?
O11 Tl1 Tl1 113.2(4) . 3_465 ?
S15 Tl1 Tl1 131.36(19) . 3_465 ?
S15 Tl1 Tl1 130.59(17) 1_556 3_465 ?
S15 Tl1 Tl1 42.0(2) 3_465 3_465 ?
S15 Tl1 Tl1 42.9(2) 3_466 3_465 ?
S16 Tl1 Tl1 75.86(11) 3_466 3_465 ?
Tl1 Tl1 Tl1 90.000(2) 1_554 3_465 ?
O11 Tl1 Tl1 105.6(4) 1_556 3_565 ?
O11 Tl1 Tl1 104.9(3) . 3_565 ?
S15 Tl1 Tl1 44.59(19) . 3_565 ?
S15 Tl1 Tl1 45.5(2) 1_556 3_565 ?
S15 Tl1 Tl1 101.31(9) 3_465 3_565 ?
S15 Tl1 Tl1 101.15(10) 3_466 3_565 ?
S16 Tl1 Tl1 53.18(11) 3_466 3_565 ?
Tl1 Tl1 Tl1 90.0 1_554 3_565 ?
Tl1 Tl1 Tl1 125.51(3) 3_465 3_565 ?
C14 S15 Tl1 115.7(9) . . ?
C14 S15 Tl1 95.5(8) . 1_554 ?
Tl1 S15 Tl1 79.61(11) . 1_554 ?
C14 S15 Tl1 117.5(8) . 3_565 ?
Tl1 S15 Tl1 93.4(4) . 3_565 ?
Tl1 S15 Tl1 145.60(17) 1_554 3_565 ?
C14 S15 Tl1 98.0(9) . 3_564 ?
Tl1 S15 Tl1 145.72(16) . 3_564 ?
Tl1 S15 Tl1 91.6(4) 1_554 3_564 ?
Tl1 S15 Tl1 75.27(10) 3_565 3_564 ?
C14 S16 C17 105.5(15) . . ?
C14 S16 Tl1 90.8(8) . 3_564 ?
C17 S16 Tl1 136.9(12) . 3_564 ?
C12 O11 Tl1 123(3) . 1_554 ?
C12 O11 Tl1 121(3) . . ?
Tl1 O11 Tl1 86.1(4) 1_554 . ?
O11 C12 C13 124(2) . . ?
O11 C12 C21B 115.9(19) . . ?
C13 C12 C21B 120(2) . . ?
O11 C12 C21A 125(2) . . ?
C13 C12 C21A 110(2) . . ?
C14 C13 C12 127(2) . . ?
C14 C13 H13 116.4 . . ?
C12 C13 H13 116.4 . . ?
C13 C14 S15 130(2) . . ?
C13 C14 S16 120(2) . . ?
S15 C14 S16 109.9(13) . . ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22A C21A C26A 120.0 . . ?
C22A C21A C12 127(2) . . ?
C26A C21A C12 109.7(18) . . ?
C21A C22A C23A 120.00(7) . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C24A C23A C22A 120.0 . . ?
C24A C23A H23A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C23A C24A C25A 120.0 . . ?
C23A C24A Cl1 110.7(15) . . ?
C25A C24A Cl1 128.5(16) . . ?
C26A C25A C24A 120.00(9) . . ?
C26A C25A H25A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C25A C26A C21A 120.00(6) . . ?
C25A C26A H26A 120.0 . . ?
C21A C26A H26A 120.0 . . ?
C22B C21B C26B 120.0 . . ?
C22B C21B C12 116(2) . . ?
C26B C21B C12 124(2) . . ?
C23B C22B C21B 120.00(8) . . ?
C23B C22B H22B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C22B C23B C24B 120.00(6) . . ?
C22B C23B H23B 120.0 . . ?
C24B C23B H23B 120.0 . . ?
C25B C24B C23B 120.0 . . ?
C25B C24B Cl2 115.4(16) . . ?
C23B C24B Cl2 123.4(16) . . ?
C24B C25B C26B 120.00(6) . . ?
C24B C25B H25B 120.0 . . ?
C26B C25B H25B 120.0 . . ?
C25B C26B C21B 120.00(6) . . ?
C25B C26B H26B 120.0 . . ?
C21B C26B H26B 120.0 . . ?

_refine_diff_density_max         2.409
_refine_diff_density_min         -1.564
_refine_diff_density_rms         0.332

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1566020'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br O S2 Tl'
_chemical_formula_weight         492.56

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tl Tl -2.8358 9.6688 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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.
;

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

_cell_length_a                   31.252(5)
_cell_length_b                   11.1332(14)
_cell_length_c                   6.9522(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2418.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8051
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      30.00

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.705
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    16.972
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            8051
_diffrn_reflns_av_unetI/netI     0.1549
_diffrn_reflns_av_R_equivalents  0.1151
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.660
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.859
_reflns_number_total             2962
_reflns_number_gt                1805
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_max     0.655
_reflns_Friedel_fraction_full    0.691

_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.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-2016/6, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2962
_refine_ls_number_parameters     137
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.951
_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_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
Tl1 Tl 0.56573(3) 0.36436(7) -0.00358(17) 0.0329(3) Uani 1 1 d . . . . .
Br24 Br 0.83146(10) 0.6376(3) -0.0648(3) 0.0468(8) Uani 1 1 d . . . . .
S15 S 0.5314(2) 0.6084(5) 0.0877(8) 0.0282(13) Uani 1 1 d . . . . .
S16 S 0.5341(2) 0.8370(5) -0.0944(8) 0.0310(14) Uani 1 1 d . . . . .
O11 O 0.6230(6) 0.5375(15) 0.161(2) 0.036(4) Uani 1 1 d . . . . .
C12 C 0.6354(8) 0.6255(19) 0.070(3) 0.028(5) Uani 1 1 d . . . . .
C13 C 0.6083(6) 0.7163(17) -0.010(4) 0.023(4) Uani 1 1 d . . . . .
H13 H 0.621662 0.779593 -0.073179 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5651(6) 0.7184(13) -0.001(5) 0.018(3) Uani 1 1 d . U . . .
C16 C 0.5710(10) 0.945(2) -0.189(4) 0.050(8) Uani 1 1 d . . . . .
H16A H 0.588417 0.975802 -0.086242 0.075 Uiso 1 1 calc R U . . .
H16B H 0.555436 1.009866 -0.247148 0.075 Uiso 1 1 calc R U . . .
H16C H 0.588893 0.907414 -0.283344 0.075 Uiso 1 1 calc R U . . .
C21 C 0.6829(7) 0.6294(17) 0.033(3) 0.023(5) Uani 1 1 d . U . . .
C22 C 0.7040(9) 0.7266(19) -0.056(3) 0.029(6) Uani 1 1 d . . . . .
H22 H 0.687810 0.792182 -0.095240 0.034 Uiso 1 1 calc R U . . .
C23 C 0.7476(8) 0.729(2) -0.086(3) 0.026(5) Uani 1 1 d . . . . .
H23 H 0.760347 0.793104 -0.150102 0.031 Uiso 1 1 calc R U . . .
C24 C 0.7721(8) 0.634(2) -0.021(5) 0.036(6) Uani 1 1 d . . . . .
C25 C 0.7520(8) 0.5348(18) 0.054(3) 0.024(5) Uani 1 1 d . . . . .
H25 H 0.768113 0.467256 0.085247 0.029 Uiso 1 1 calc R U . . .
C26 C 0.7082(8) 0.5334(18) 0.084(3) 0.025(5) Uani 1 1 d . . . . .
H26 H 0.695619 0.466315 0.140299 0.030 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
Tl1 O11 2.869(16) . ?
Tl1 S15 2.989(6) . ?
Tl1 S15 3.053(6) 7_454 ?
Tl1 S15 3.115(6) 2_665 ?
Tl1 O11 3.137(17) 7_454 ?
Tl1 Tl1 4.6049(10) 7_455 ?
Tl1 Tl1 4.6049(10) 7_454 ?
Br24 C24 1.88(2) . ?
S15 C14 1.73(2) . ?
S16 C14 1.76(2) . ?
S16 C16 1.79(3) . ?
O11 C12 1.23(2) . ?
C12 C13 1.43(3) . ?
C12 C21 1.51(3) . ?
C13 C14 1.35(3) . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C21 C26 1.38(3) . ?
C21 C22 1.41(3) . ?
C22 C23 1.38(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.38(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.37(3) . ?
C25 C26 1.39(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
O11 Tl1 S15 61.9(4) . . ?
O11 Tl1 S15 121.6(3) . 7_454 ?
S15 Tl1 S15 88.91(14) . 7_454 ?
O11 Tl1 S15 117.5(4) . 2_665 ?
S15 Tl1 S15 61.21(19) . 2_665 ?
S15 Tl1 S15 80.64(11) 7_454 2_665 ?
O11 Tl1 O11 72.9(4) . 7_454 ?
S15 Tl1 O11 92.7(3) . 7_454 ?
S15 Tl1 O11 58.3(3) 7_454 7_454 ?
S15 Tl1 O11 132.4(3) 2_665 7_454 ?
O11 Tl1 Tl1 42.1(3) . 7_455 ?
S15 Tl1 Tl1 40.86(11) . 7_455 ?
S15 Tl1 Tl1 129.60(11) 7_454 7_455 ?
S15 Tl1 Tl1 77.43(10) 2_665 7_455 ?
O11 Tl1 Tl1 109.4(3) 7_454 7_455 ?
O11 Tl1 Tl1 82.0(3) . 7_454 ?
S15 Tl1 Tl1 64.16(11) . 7_454 ?
S15 Tl1 Tl1 39.84(11) 7_454 7_454 ?
S15 Tl1 Tl1 95.16(11) 2_665 7_454 ?
O11 Tl1 Tl1 37.8(3) 7_454 7_454 ?
Tl1 Tl1 Tl1 98.03(3) 7_455 7_454 ?
C14 S15 Tl1 110.4(7) . . ?
C14 S15 Tl1 92.7(11) . 7_455 ?
Tl1 S15 Tl1 99.30(17) . 7_455 ?
C14 S15 Tl1 116.9(8) . 2_665 ?
Tl1 S15 Tl1 113.27(18) . 2_665 ?
Tl1 S15 Tl1 121.5(2) 7_455 2_665 ?
C14 S16 C16 106.4(12) . . ?
C12 O11 Tl1 121.8(13) . . ?
C12 O11 Tl1 106.6(15) . 7_455 ?
Tl1 O11 Tl1 100.0(5) . 7_455 ?
O11 C12 C13 125(2) . . ?
O11 C12 C21 115(2) . . ?
C13 C12 C21 119.7(19) . . ?
C14 C13 C12 126(2) . . ?
C14 C13 H13 117.0 . . ?
C12 C13 H13 117.0 . . ?
C13 C14 S15 127.7(16) . . ?
C13 C14 S16 123.2(17) . . ?
S15 C14 S16 109.0(11) . . ?
S16 C16 H16A 109.5 . . ?
S16 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S16 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C21 C22 116(2) . . ?
C26 C21 C12 119.9(19) . . ?
C22 C21 C12 124(2) . . ?
C23 C22 C21 123(2) . . ?
C23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C22 C23 C24 119(2) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C24 C23 119(2) . . ?
C25 C24 Br24 122.0(18) . . ?
C23 C24 Br24 118.4(19) . . ?
C26 C25 C24 121(2) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C21 C26 C25 121(2) . . ?
C21 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?

_refine_diff_density_max         3.218
_refine_diff_density_min         -2.223
_refine_diff_density_rms         0.347

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1566019'
_audit_update_record             
;
2018-10-04 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 N O S2 Tl'
_chemical_formula_weight         414.65

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'
N N 0.0061 0.0033 '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'
Tl Tl -2.8358 9.6688 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

_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.
;

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

_cell_length_a                   10.9680(7)
_cell_length_b                   27.114(2)
_cell_length_c                   7.1755(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2133.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    14954
_cell_measurement_theta_min      2.920
_cell_measurement_theta_max      28.339

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.581
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    15.493
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5192
_exptl_absorpt_correction_T_max  0.8417
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest SCM Diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14954
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.920
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2655
_reflns_number_gt                2197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.015(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.002
_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_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
Tl1 Tl 0.35442(3) 0.57304(2) 0.53482(10) 0.04640(15) Uani 1 1 d . . . . .
O11 O 0.5278(7) 0.6415(3) 0.3852(13) 0.067(2) Uani 1 1 d . . . . .
C12 C 0.6197(8) 0.6571(3) 0.4673(13) 0.0341(19) Uani 1 1 d . . . . .
C13 C 0.7144(7) 0.6267(2) 0.5389(18) 0.0326(15) Uani 1 1 d . . . . .
H13 H 0.780861 0.642802 0.598120 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7182(7) 0.5763(2) 0.530(2) 0.0284(14) Uani 1 1 d . . . . .
S15 S 0.6084(2) 0.53734(8) 0.4439(4) 0.0421(5) Uani 1 1 d . . . . .
S16 S 0.8396(2) 0.54156(9) 0.6178(4) 0.0421(6) Uani 1 1 d . . . . .
C17 C 0.9495(9) 0.5847(4) 0.7069(16) 0.046(2) Uani 1 1 d . . . . .
H17A H 0.968189 0.609324 0.610936 0.069 Uiso 1 1 calc R U . . .
H17B H 1.024245 0.567139 0.741286 0.069 Uiso 1 1 calc R U . . .
H17C H 0.916028 0.601285 0.816999 0.069 Uiso 1 1 calc R U . . .
C21 C 0.6278(7) 0.7121(4) 0.4827(10) 0.029(2) Uani 1 1 d . . . . .
C22 C 0.5343(8) 0.7405(3) 0.4136(11) 0.0321(19) Uani 1 1 d . . . . .
H22 H 0.465008 0.725128 0.359511 0.039 Uiso 1 1 calc R U . . .
C23 C 0.5406(8) 0.7916(3) 0.4226(12) 0.038(2) Uani 1 1 d . . . . .
H23 H 0.472996 0.810019 0.377659 0.046 Uiso 1 1 calc R U . . .
N24 N 0.6361(6) 0.8166(3) 0.4908(10) 0.038(2) Uani 1 1 d . . . . .
C25 C 0.7269(8) 0.7890(3) 0.5566(17) 0.037(2) Uani 1 1 d . . . . .
H25 H 0.796921 0.805573 0.603216 0.044 Uiso 1 1 calc R U . . .
C26 C 0.7268(8) 0.7384(3) 0.5620(13) 0.031(2) Uani 1 1 d . . . . .
H26 H 0.792441 0.721171 0.618457 0.037 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
Tl1 O11 2.867(8) . ?
Tl1 S15 3.020(3) . ?
Tl1 S15 3.090(2) 2_665 ?
Tl1 S15 3.118(3) 8_545 ?
Tl1 Tl1 4.8032(5) 8_545 ?
Tl1 Tl1 4.8032(5) 8_544 ?
O11 C12 1.241(11) . ?
C12 C13 1.422(12) . ?
C12 C21 1.499(13) . ?
C13 C14 1.369(9) . ?
C13 H13 0.9500 . ?
C14 S15 1.717(9) . ?
C14 S16 1.748(9) . ?
S16 C17 1.798(10) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C22 1.375(12) . ?
C21 C26 1.418(11) . ?
C22 C23 1.389(12) . ?
C22 H22 0.9500 . ?
C23 N24 1.340(11) . ?
C23 H23 0.9500 . ?
N24 C25 1.333(11) . ?
C25 C26 1.372(10) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
O11 Tl1 S15 60.99(16) . . ?
O11 Tl1 S15 117.44(18) . 2_665 ?
S15 Tl1 S15 61.46(7) . 2_665 ?
O11 Tl1 S15 117.84(16) . 8_545 ?
S15 Tl1 S15 89.04(6) . 8_545 ?
S15 Tl1 S15 83.16(5) 2_665 8_545 ?
O11 Tl1 Tl1 80.72(15) . 8_545 ?
S15 Tl1 Tl1 63.14(6) . 8_545 ?
S15 Tl1 Tl1 94.01(5) 2_665 8_545 ?
S15 Tl1 Tl1 37.79(5) 8_545 8_545 ?
O11 Tl1 Tl1 43.88(18) . 8_544 ?
S15 Tl1 Tl1 39.24(6) . 8_544 ?
S15 Tl1 Tl1 75.79(5) 2_665 8_544 ?
S15 Tl1 Tl1 128.04(4) 8_545 8_544 ?
Tl1 Tl1 Tl1 96.655(13) 8_545 8_544 ?
C12 O11 Tl1 125.5(7) . . ?
O11 C12 C13 124.6(8) . . ?
O11 C12 C21 114.9(8) . . ?
C13 C12 C21 120.4(7) . . ?
C14 C13 C12 125.7(8) . . ?
C14 C13 H13 117.1 . . ?
C12 C13 H13 117.1 . . ?
C13 C14 S15 127.5(7) . . ?
C13 C14 S16 123.0(8) . . ?
S15 C14 S16 109.4(3) . . ?
C14 S15 Tl1 111.9(3) . . ?
C14 S15 Tl1 115.3(3) . 2_665 ?
Tl1 S15 Tl1 112.74(8) . 2_665 ?
C14 S15 Tl1 93.2(5) . 8_544 ?
Tl1 S15 Tl1 102.98(8) . 8_544 ?
Tl1 S15 Tl1 118.83(9) 2_665 8_544 ?
C14 S16 C17 106.7(4) . . ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 C26 115.7(9) . . ?
C22 C21 C12 119.1(8) . . ?
C26 C21 C12 125.2(8) . . ?
C21 C22 C23 120.3(8) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
N24 C23 C22 124.1(8) . . ?
N24 C23 H23 117.9 . . ?
C22 C23 H23 117.9 . . ?
C25 N24 C23 115.4(8) . . ?
N24 C25 C26 124.8(8) . . ?
N24 C25 H25 117.6 . . ?
C26 C25 H25 117.6 . . ?
C25 C26 C21 119.5(8) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?

_refine_diff_density_max         0.651
_refine_diff_density_min         -1.848
_refine_diff_density_rms         0.274

####################################################################### 
# 
# 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_HL5
_database_code_depnum_ccdc_archive 'CCDC 1842769'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 O S2'
_chemical_formula_weight         310.41

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6083(7)
_cell_length_b                   9.1906(8)
_cell_length_c                   10.2695(8)
_cell_angle_alpha                78.227(7)
_cell_angle_beta                 68.521(7)
_cell_angle_gamma                78.296(7)
_cell_volume                     732.79(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5170
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.358
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'

_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  1.000


_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Oxford Diffaction X-Calibor System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            5170
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.672
_diffrn_reflns_theta_max         29.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4074
_reflns_number_gt                3460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL, PLATON, WINGX (Ferrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.1767P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4074
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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_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
O11 O 0.28678(14) 1.15557(13) -0.41188(11) 0.0258(2) Uani 1 1 d D . . . .
H11 H 0.346(2) 1.0781(19) -0.395(2) 0.039 Uiso 1 1 d D U . . .
C12 C 0.18637(17) 1.18985(15) -0.28522(14) 0.0175(3) Uani 1 1 d . . . . .
C13 C 0.19975(18) 1.11342(16) -0.16084(15) 0.0208(3) Uani 1 1 d . . . . .
H13 H 0.122051 1.146843 -0.078522 0.025 Uiso 1 1 calc R U . . .
C14 C 0.32170(18) 0.98665(16) -0.14437(15) 0.0195(3) Uani 1 1 d . . . . .
S15 S 0.47348(5) 0.90852(4) -0.27586(4) 0.02691(11) Uani 1 1 d . . . . .
S16 S 0.29026(5) 0.91995(5) 0.03274(4) 0.03034(12) Uani 1 1 d . . . . .
C17 C 0.4540(2) 0.7649(2) 0.03196(19) 0.0341(4) Uani 1 1 d . . . . .
H17A H 0.438956 0.687437 -0.010629 0.051 Uiso 1 1 calc R U . . .
H17B H 0.449448 0.726460 0.127311 0.051 Uiso 1 1 calc R U . . .
H17C H 0.561540 0.797722 -0.021222 0.051 Uiso 1 1 calc R U . . .
C21 C 0.05515(17) 1.32041(15) -0.29195(14) 0.0173(3) Uani 1 1 d . . . . .
C22 C -0.07026(17) 1.30770(15) -0.34474(13) 0.0176(3) Uani 1 1 d . . . . .
C23 C -0.08399(18) 1.17056(16) -0.38203(15) 0.0214(3) Uani 1 1 d . . . . .
H23 H -0.006348 1.085892 -0.373251 0.026 Uiso 1 1 calc R U . . .
C24 C -0.2088(2) 1.16212(19) -0.43010(16) 0.0278(3) Uani 1 1 d . . . . .
H24 H -0.216058 1.071612 -0.453239 0.033 Uiso 1 1 calc R U . . .
C25 C -0.3279(2) 1.2894(2) -0.44543(18) 0.0315(4) Uani 1 1 d . . . . .
H25 H -0.411824 1.282037 -0.479625 0.038 Uiso 1 1 calc R U . . .
C26 C -0.3208(2) 1.42151(19) -0.41080(17) 0.0281(3) Uani 1 1 d . . . . .
H26 H -0.399895 1.504311 -0.421475 0.034 Uiso 1 1 calc R U . . .
C27 C -0.19291(18) 1.43520(16) -0.35792(15) 0.0205(3) Uani 1 1 d . . . . .
C28 C -0.18554(19) 1.56909(16) -0.31880(16) 0.0237(3) Uani 1 1 d . . . . .
H28 H -0.264456 1.652177 -0.329061 0.028 Uiso 1 1 calc R U . . .
C29 C -0.06367(18) 1.58227(16) -0.26483(15) 0.0210(3) Uani 1 1 d . . . . .
C30 C -0.0560(2) 1.72110(17) -0.22770(17) 0.0286(3) Uani 1 1 d . . . . .
H30 H -0.136180 1.803511 -0.236818 0.034 Uiso 1 1 calc R U . . .
C31 C 0.0661(2) 1.73478(19) -0.17942(17) 0.0321(4) Uani 1 1 d . . . . .
H31 H 0.069882 1.826334 -0.156185 0.039 Uiso 1 1 calc R U . . .
C32 C 0.1882(2) 1.6098(2) -0.16417(18) 0.0332(4) Uani 1 1 d . . . . .
H32 H 0.271108 1.620045 -0.130084 0.040 Uiso 1 1 calc R U . . .
C33 C 0.1862(2) 1.47506(18) -0.19853(17) 0.0269(3) Uani 1 1 d . . . . .
H33 H 0.268025 1.394707 -0.188117 0.032 Uiso 1 1 calc R U . . .
C34 C 0.06015(18) 1.45552(16) -0.25033(14) 0.0194(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C12 1.3310(16) . ?
O11 H11 0.818(15) . ?
C12 C13 1.3591(19) . ?
C12 C21 1.4813(18) . ?
C13 C14 1.4288(19) . ?
C13 H13 0.9300 . ?
C14 S15 1.6641(14) . ?
C14 S16 1.7347(14) . ?
S16 C17 1.7884(17) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 C22 1.4065(19) . ?
C21 C34 1.4065(19) . ?
C22 C23 1.4282(19) . ?
C22 C27 1.4298(19) . ?
C23 C24 1.357(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.414(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.352(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.430(2) . ?
C26 H26 0.9300 . ?
C27 C28 1.390(2) . ?
C28 C29 1.388(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.424(2) . ?
C29 C34 1.434(2) . ?
C30 C31 1.352(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.416(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.360(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.426(2) . ?
C33 H33 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
C12 O11 H11 104.3(15) . . ?
O11 C12 C13 124.22(13) . . ?
O11 C12 C21 113.30(12) . . ?
C13 C12 C21 122.48(12) . . ?
C12 C13 C14 126.27(12) . . ?
C12 C13 H13 116.9 . . ?
C14 C13 H13 116.9 . . ?
C13 C14 S15 125.37(11) . . ?
C13 C14 S16 111.29(10) . . ?
S15 C14 S16 123.33(9) . . ?
C14 S16 C17 104.79(8) . . ?
S16 C17 H17A 109.5 . . ?
S16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 C34 121.08(13) . . ?
C22 C21 C12 118.72(12) . . ?
C34 C21 C12 120.17(12) . . ?
C21 C22 C23 122.68(13) . . ?
C21 C22 C27 119.21(13) . . ?
C23 C22 C27 118.08(13) . . ?
C24 C23 C22 120.91(14) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.76(15) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 120.57(15) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.63(15) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C22 119.41(13) . . ?
C28 C27 C26 121.57(14) . . ?
C22 C27 C26 119.02(14) . . ?
C29 C28 C27 121.85(13) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C30 121.11(14) . . ?
C28 C29 C34 119.60(13) . . ?
C30 C29 C34 119.26(14) . . ?
C31 C30 C29 120.94(15) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 120.05(15) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 121.12(16) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 120.79(16) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C21 C34 C33 123.29(13) . . ?
C21 C34 C29 118.85(13) . . ?
C33 C34 C29 117.83(13) . . ?

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
O11 C12 C13 C14 0.5(2) . . . . ?
C21 C12 C13 C14 179.93(14) . . . . ?
C12 C13 C14 S15 0.6(2) . . . . ?
C12 C13 C14 S16 -178.29(13) . . . . ?
C13 C14 S16 C17 -179.38(11) . . . . ?
S15 C14 S16 C17 1.67(13) . . . . ?
O11 C12 C21 C22 65.66(17) . . . . ?
C13 C12 C21 C22 -113.80(16) . . . . ?
O11 C12 C21 C34 -112.34(14) . . . . ?
C13 C12 C21 C34 68.19(19) . . . . ?
C34 C21 C22 C23 -177.10(13) . . . . ?
C12 C21 C22 C23 4.92(19) . . . . ?
C34 C21 C22 C27 0.89(19) . . . . ?
C12 C21 C22 C27 -177.10(12) . . . . ?
C21 C22 C23 C24 178.74(13) . . . . ?
C27 C22 C23 C24 0.7(2) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C23 C24 C25 C26 -0.8(2) . . . . ?
C24 C25 C26 C27 -0.1(2) . . . . ?
C21 C22 C27 C28 0.2(2) . . . . ?
C23 C22 C27 C28 178.27(13) . . . . ?
C21 C22 C27 C26 -179.61(13) . . . . ?
C23 C22 C27 C26 -1.54(19) . . . . ?
C25 C26 C27 C28 -178.58(15) . . . . ?
C25 C26 C27 C22 1.2(2) . . . . ?
C22 C27 C28 C29 -1.1(2) . . . . ?
C26 C27 C28 C29 178.73(14) . . . . ?
C27 C28 C29 C30 178.83(13) . . . . ?
C27 C28 C29 C34 0.9(2) . . . . ?
C28 C29 C30 C31 -177.88(15) . . . . ?
C34 C29 C30 C31 0.1(2) . . . . ?
C29 C30 C31 C32 -0.4(2) . . . . ?
C30 C31 C32 C33 0.6(3) . . . . ?
C31 C32 C33 C34 -0.3(3) . . . . ?
C22 C21 C34 C33 -178.87(13) . . . . ?
C12 C21 C34 C33 -0.9(2) . . . . ?
C22 C21 C34 C29 -1.1(2) . . . . ?
C12 C21 C34 C29 176.86(12) . . . . ?
C32 C33 C34 C21 177.80(14) . . . . ?
C32 C33 C34 C29 0.0(2) . . . . ?
C28 C29 C34 C21 0.2(2) . . . . ?
C30 C29 C34 C21 -177.78(13) . . . . ?
C28 C29 C34 C33 178.12(13) . . . . ?
C30 C29 C34 C33 0.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O11 H11 S15 0.818(15) 2.150(16) 2.9256(12) 158(2) .

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.056

