# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ybtx1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1911704'
loop_
_audit_author_name
_audit_author_address
'Yating Wen'
;Jilin University
China
;
_audit_update_record             
;
2019-04-23 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-chloro-9H-thioxanthen-9-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 Cl O S'
_chemical_formula_weight         246.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   3.8774(3)
_cell_length_b                   7.2116(6)
_cell_length_c                   19.1149(14)
_cell_angle_alpha                88.416(6)
_cell_angle_beta                 88.918(6)
_cell_angle_gamma                82.032(6)
_cell_volume                     529.07(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    2402
_cell_measurement_theta_min      2.31?
_cell_measurement_theta_max      54.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    4.796
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8357
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_max         54.491
_diffrn_reflns_theta_full        54.491
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1290
_reflns_number_gt                828
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²+0.2105P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1290
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_restrained_S_all      0.876
_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
S1 S 0.2115(4) 0.90025(18) 0.76893(7) 0.0458(5) Uani 1 1 d . . . . .
Cl1 Cl 0.8751(4) 0.1873(2) 0.93515(7) 0.0632(6) Uani 1 1 d . . . . .
O1 O 0.3202(11) 0.3229(5) 0.6896(2) 0.0704(13) Uani 1 1 d . . . . .
C13 C 0.4140(13) 0.5161(7) 0.7820(3) 0.0357(13) Uani 1 1 d . . . . .
C8 C 0.3899(12) 0.6943(7) 0.8101(3) 0.0362(14) Uani 1 1 d . . . . .
C2 C 0.1169(13) 0.6403(7) 0.6689(3) 0.0380(14) Uani 1 1 d . . . . .
C7 C 0.0783(13) 0.8271(7) 0.6896(3) 0.0373(14) Uani 1 1 d . . . . .
C9 C 0.5207(13) 0.7113(8) 0.8769(3) 0.0410(15) Uani 1 1 d . . . . .
C11 C 0.6869(13) 0.3818(8) 0.8865(3) 0.0432(15) Uani 1 1 d . . . . .
C12 C 0.5673(14) 0.3628(9) 0.8212(3) 0.0451(16) Uani 1 1 d . . . . .
C10 C 0.6672(15) 0.5600(8) 0.9144(3) 0.0452(15) Uani 1 1 d . . . . .
C1 C 0.2859(14) 0.4835(8) 0.7117(3) 0.0441(15) Uani 1 1 d . . . . .
C6 C -0.0848(15) 0.9686(10) 0.6450(3) 0.0523(16) Uani 1 1 d . . . . .
C3 C -0.0151(16) 0.6040(9) 0.6036(3) 0.0507(16) Uani 1 1 d . . . . .
C5 C -0.2048(17) 0.9241(10) 0.5811(3) 0.0580(18) Uani 1 1 d . . . . .
C4 C -0.1683(15) 0.7405(10) 0.5597(3) 0.0543(17) Uani 1 1 d . . . . .
H4 H 0.519(11) 0.841(6) 0.895(2) 0.029(12) Uiso 1 1 d . . . . .
H6 H 0.578(11) 0.250(7) 0.800(2) 0.039(16) Uiso 1 1 d . . . . .
H2 H -0.278(13) 0.703(7) 0.511(3) 0.057(15) Uiso 1 1 d . . . . .
H5 H 0.760(14) 0.566(7) 0.959(3) 0.067(19) Uiso 1 1 d . . . . .
H1 H 0.017(13) 0.466(8) 0.591(3) 0.055(16) Uiso 1 1 d . . . . .
H3 H -0.301(14) 1.024(8) 0.556(3) 0.07(2) Uiso 1 1 d . . . . .
H7 H -0.093(14) 1.095(9) 0.656(3) 0.062(19) Uiso 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
S1 C8 1.725(5) . ?
S1 C7 1.730(5) . ?
Cl1 C11 1.741(5) . ?
O1 C1 1.233(6) . ?
C13 C12 1.387(7) . ?
C13 C8 1.398(7) . ?
C13 C1 1.477(7) . ?
C8 C9 1.397(7) . ?
C2 C7 1.402(7) . ?
C2 C3 1.403(7) . ?
C2 C1 1.462(7) . ?
C7 C6 1.400(7) . ?
C9 C10 1.352(7) . ?
C9 H4 1.01(4) . ?
C11 C12 1.358(7) . ?
C11 C10 1.396(7) . ?
C12 H6 0.91(4) . ?
C10 H5 0.94(5) . ?
C6 C5 1.377(8) . ?
C6 H7 0.94(6) . ?
C3 C4 1.356(8) . ?
C3 H1 1.02(5) . ?
C5 C4 1.384(8) . ?
C5 H3 0.90(6) . ?
C4 H2 1.09(5) . ?

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
C8 S1 C7 103.4(3) . . ?
C12 C13 C8 118.9(5) . . ?
C12 C13 C1 118.3(5) . . ?
C8 C13 C1 122.8(5) . . ?
C9 C8 C13 118.6(5) . . ?
C9 C8 S1 116.0(4) . . ?
C13 C8 S1 125.4(4) . . ?
C7 C2 C3 117.5(5) . . ?
C7 C2 C1 123.5(5) . . ?
C3 C2 C1 119.0(5) . . ?
C6 C7 C2 119.6(5) . . ?
C6 C7 S1 115.7(5) . . ?
C2 C7 S1 124.7(4) . . ?
C10 C9 C8 121.5(6) . . ?
C10 C9 H4 120(2) . . ?
C8 C9 H4 118(2) . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 Cl1 120.8(5) . . ?
C10 C11 Cl1 119.6(5) . . ?
C11 C12 C13 121.6(6) . . ?
C11 C12 H6 123(3) . . ?
C13 C12 H6 116(3) . . ?
C9 C10 C11 119.8(6) . . ?
C9 C10 H5 124(3) . . ?
C11 C10 H5 116(3) . . ?
O1 C1 C2 120.3(5) . . ?
O1 C1 C13 119.4(5) . . ?
C2 C1 C13 120.3(5) . . ?
C5 C6 C7 120.1(7) . . ?
C5 C6 H7 119(3) . . ?
C7 C6 H7 120(3) . . ?
C4 C3 C2 123.2(6) . . ?
C4 C3 H1 122(3) . . ?
C2 C3 H1 115(3) . . ?
C6 C5 C4 121.2(6) . . ?
C6 C5 H3 114(4) . . ?
C4 C5 H3 125(4) . . ?
C3 C4 C5 118.4(6) . . ?
C3 C4 H2 120(3) . . ?
C5 C4 H2 122(3) . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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 1911710'
loop_
_audit_author_name
_audit_author_address
'Yating Wen'
;Jilin University
China
;
_audit_update_record             
;
2019-04-23 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        9H-thioxanthen-9-one
_chemical_formula_moiety         'C13 H8 O S'
_chemical_formula_sum            'C13 H8 O S'
_chemical_formula_weight         212.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.6308(10)
_cell_length_b                   3.9100(2)
_cell_length_c                   15.6582(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.879(2)
_cell_angle_gamma                90
_cell_volume                     939.77(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.450
_cell_measurement_theta_min      3.378
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29944
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.509
_diffrn_reflns_theta_min         2.730
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2129
_reflns_number_total             3338
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -1.165
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²+0.9946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1689
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.2516(16)
 0.7484(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C1A) = Uanis(O1) = Uanis(O1A) = Uanis(S1) = Uanis(S1A)
4. Others
 Sof(S1A)=Sof(O1A)=Sof(C1A)=1-FVAR(1)
 Sof(S1)=Sof(O1)=Sof(C1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C0AA(H0AA), C5(H5), C10(H10), C12(H12), C13(H13), C17(H17), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32611(9) 0.9787(4) 0.41957(9) 0.01651(17) Uani 0.4989(18) 1 d . . P A 1
O1 O 0.1453(2) 1.0321(9) 0.6066(2) 0.01651(17) Uani 0.4989(18) 1 d . . P A 1
C1 C 0.1955(3) 1.0135(14) 0.5558(4) 0.01651(17) Uani 0.4989(18) 1 d . . P A 1
C2 C 0.21683(16) 0.8426(9) 0.41236(19) 0.0211(6) Uani 1 1 d . . . . .
C3 C 0.4241(2) 1.2694(7) 0.5528(2) 0.0210(7) Uani 1 1 d . . . . .
H3 H 0.462907 1.258242 0.512972 0.025 Uiso 1 1 calc R . . . .
C4 C 0.16083(18) 0.8594(9) 0.47162(17) 0.0201(5) Uani 1 1 d . . . . .
C0AA C 0.39577(17) 1.4273(8) 0.69374(17) 0.0215(6) Uani 1 1 d . . . . .
H0AA H 0.414543 1.524644 0.749731 0.026 Uiso 1 1 calc R . . . .
C5 C 0.0757(2) 0.7304(7) 0.4468(2) 0.0221(8) Uani 1 1 d . . . . .
H5 H 0.036718 0.741690 0.486436 0.026 Uiso 1 1 calc R . . . .
C6 C 0.28300(16) 1.1554(9) 0.58765(19) 0.0201(6) Uani 1 1 d . . . . .
C8 C 0.33957(18) 1.1414(9) 0.52862(17) 0.0201(5) Uani 1 1 d . . . . .
C10 C 0.10432(17) 0.5723(8) 0.30652(17) 0.0222(6) Uani 1 1 d . . . . .
H10 H 0.084897 0.475100 0.250618 0.027 Uiso 1 1 calc R . . . .
C12 C 0.45209(16) 1.4126(8) 0.63434(18) 0.0215(6) Uani 1 1 d . . . . .
H12 H 0.509579 1.500646 0.649805 0.026 Uiso 1 1 calc R . . . .
C13 C 0.04816(16) 0.5880(8) 0.36577(18) 0.0212(6) Uani 1 1 d . . . . .
H13 H -0.009348 0.500177 0.350243 0.025 Uiso 1 1 calc R . . . .
C17 C 0.1880(2) 0.6976(9) 0.3289(2) 0.0226(7) Uani 1 1 d . . . . .
H17 H 0.226256 0.686839 0.288451 0.027 Uiso 1 1 calc R . . . .
C20 C 0.3131(2) 1.2993(9) 0.6701(2) 0.0223(7) Uani 1 1 d . . . . .
H20 H 0.274921 1.308180 0.710594 0.027 Uiso 1 1 calc R . . . .


_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
S1 C2 1.772(3) . ?
S1 C8 1.797(3) . ?
O1 C1 1.220(6) . ?
C1 C4 1.458(6) . ?
C1 C6 1.473(5) . ?
S1A C4 1.794(3) . ?
S1A C6 1.770(3) . ?
O1A C1A 1.207(6) . ?
C1A C2 1.480(6) . ?
C1A C8 1.461(6) . ?
C2 C4 1.392(4) . ?
C2 C17 1.418(4) . ?
C3 C8 1.397(4) . ?
C3 C12 1.387(4) . ?
C4 C5 1.407(4) . ?
C0AA C12 1.397(3) . ?
C0AA C20 1.370(4) . ?
C5 C13 1.378(4) . ?
C6 C8 1.396(3) . ?
C6 C20 1.405(4) . ?
C10 C13 1.394(3) . ?
C10 C17 1.379(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C8 96.05(16) . . ?
O1 C1 C4 116.0(4) . . ?
O1 C1 C6 115.3(4) . . ?
C4 C1 C6 128.7(5) . . ?
C6 S1A C4 95.66(16) . . ?
O1A C1A C2 114.1(4) . . ?
O1A C1A C8 116.9(4) . . ?
C8 C1A C2 128.9(5) . . ?
C4 C2 S1 131.5(2) . . ?
C4 C2 C1A 114.6(3) . . ?
C4 C2 C17 120.2(3) . . ?
C17 C2 S1 108.3(2) . . ?
C17 C2 C1A 125.2(3) . . ?
C12 C3 C8 120.8(3) . . ?
C2 C4 C1 116.7(3) . . ?
C2 C4 S1A 132.7(2) . . ?
C2 C4 C5 118.6(3) . . ?
C5 C4 C1 124.7(3) . . ?
C5 C4 S1A 108.7(2) . . ?
C20 C0AA C12 119.0(3) . . ?
C13 C5 C4 121.0(3) . . ?
C8 C6 C1 115.1(3) . . ?
C8 C6 S1A 132.1(2) . . ?
C8 C6 C20 118.7(3) . . ?
C20 C6 C1 126.2(3) . . ?
C20 C6 S1A 109.2(2) . . ?
C3 C8 S1 108.7(2) . . ?
C3 C8 C1A 124.6(3) . . ?
C6 C8 S1 131.9(2) . . ?
C6 C8 C1A 116.0(3) . . ?
C6 C8 C3 119.4(3) . . ?
C17 C10 C13 120.1(3) . . ?
C3 C12 C0AA 120.0(3) . . ?
C5 C13 C10 120.2(3) . . ?
C10 C17 C2 119.8(3) . . ?
C0AA C20 C6 122.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.2516(16)
2 0.7484(16)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 1911705'
loop_
_audit_author_name
_audit_author_address
'Yating Wen'
;Jilin University
China
;
_audit_update_record             
;
2019-04-23 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-bromo-9H-thioxanthen-9-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 Br H0 O S'
_chemical_formula_weight         284.10

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9237(10)
_cell_length_b                   7.2727(19)
_cell_length_c                   19.173(5)
_cell_angle_alpha                88.393(4)
_cell_angle_beta                 88.616(4)
_cell_angle_gamma                82.487(4)
_cell_volume                     542.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1122
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      25.14

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellowish
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             274
_exptl_absorpt_coefficient_mu    3.953
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4633
_exptl_absorpt_correction_T_max  0.5205
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3390
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.30
_reflns_number_total             2186
_reflns_number_gt                1637
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1272P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2186
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1913
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.38424(17) 0.17600(8) 0.43498(3) 0.0510(3) Uani 1 1 d . . .
S1 S 0.7089(4) 0.89932(19) 0.26615(8) 0.0419(4) Uani 1 1 d . . .
O1 O 0.8122(17) 0.3275(6) 0.1863(3) 0.0722(17) Uani 1 1 d . . .
C1 C 1.1859(7) 0.3840(3) 0.38425(13) 0.0379(13) Uani 1 1 d G . .
C2 C 1.1645(8) 0.5597(4) 0.41203(12) 0.0428(14) Uani 1 1 d G . .
C3 C 1.0167(9) 0.7138(3) 0.37386(12) 0.0400(13) Uani 1 1 d G . .
C4 C 0.8903(6) 0.6922(2) 0.30790(11) 0.0336(12) Uani 1 1 d G . .
C5 C 0.9117(6) 0.5165(2) 0.28011(11) 0.0337(12) Uani 1 1 d G . .
C6 C 1.0595(8) 0.3624(3) 0.31828(13) 0.0385(13) Uani 1 1 d G . .
C7 C 0.5649(6) 0.8326(3) 0.18555(11) 0.0372(13) Uani 1 1 d G . .
C8 C 0.4113(9) 0.9736(3) 0.14292(14) 0.0494(16) Uani 1 1 d G . .
C9 C 0.2981(8) 0.9229(4) 0.07907(13) 0.0527(17) Uani 1 1 d G . .
C10 C 0.3324(9) 0.7439(4) 0.05852(12) 0.0570(18) Uani 1 1 d G . .
C11 C 0.4807(10) 0.6066(4) 0.09768(13) 0.0523(17) Uani 1 1 d G . .
C12 C 0.6011(6) 0.6481(3) 0.16660(11) 0.0386(13) Uani 1 1 d G . .
C13 C 0.7762(16) 0.4861(8) 0.2080(3) 0.0394(14) 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
Br1 C1 1.867(2) . ?
S1 C4 1.760(2) . ?
S1 C7 1.760(3) . ?
O1 C13 1.226(7) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C13 1.525(6) . ?
C7 C8 1.3775 . ?
C7 C12 1.3881 . ?
C8 C9 1.3878 . ?
C9 C10 1.3597 . ?
C10 C11 1.3140 . ?
C11 C12 1.4665 . ?
C12 C13 1.501(6) . ?

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
C4 S1 C7 105.45(11) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 Br1 120.40(12) . . ?
C6 C1 Br1 119.60(12) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 S1 125.18(8) . . ?
C3 C4 S1 114.82(8) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C13 118.2(2) . . ?
C4 C5 C13 121.8(2) . . ?
C5 C6 C1 120.0 . . ?
C8 C7 C12 122.1 . . ?
C8 C7 S1 116.15(7) . . ?
C12 C7 S1 121.73(7) . . ?
C7 C8 C9 116.7 . . ?
C10 C9 C8 122.7 . . ?
C11 C10 C9 122.0 . . ?
C10 C11 C12 118.6 . . ?
C7 C12 C11 117.8 . . ?
C7 C12 C13 126.1(2) . . ?
C11 C12 C13 116.0(2) . . ?
O1 C13 C12 122.3(5) . . ?
O1 C13 C5 118.1(5) . . ?
C12 C13 C5 119.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.068
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.151
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_b_a
_database_code_depnum_ccdc_archive 'CCDC 1911709'
loop_
_audit_author_name
_audit_author_address
'Yating Wen'
;Jilin University
China
;
_audit_update_record             
;
2019-04-23 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        2-iodo-9H-thioxanthen-9-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 I O S'
_chemical_formula_weight         1782.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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                   4.1712(3)
_cell_length_b                   6.1807(4)
_cell_length_c                   43.775(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1128.57(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.623
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.476
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      289(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17654
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.1522
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.018
_diffrn_reflns_theta_max         59.028
_diffrn_reflns_theta_full        59.028
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1642
_reflns_number_gt                1517
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.582
_reflns_Friedel_fraction_max     0.997
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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+4.1341P] 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 503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.126(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1642
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
I1 I 0.9217(3) -0.12394(15) 0.27876(2) 0.0419(4) Uani 1 1 d . . . . .
S1 S 0.4196(12) 0.6003(5) 0.37838(9) 0.0448(10) Uani 1 1 d . . . . .
O1 O 1.011(4) 0.0320(19) 0.4026(3) 0.061(4) Uani 1 1 d . . . . .
C1 C 0.554(4) 0.524(2) 0.4149(3) 0.033(3) Uani 1 1 d . . . . .
C2 C 0.582(5) 0.275(2) 0.3025(3) 0.039(3) Uani 1 1 d . . . . .
H2A H 0.529013 0.292278 0.281973 0.047 Uiso 1 1 calc R U . . .
C3 C 0.730(4) 0.336(2) 0.4205(3) 0.036(3) Uani 1 1 d . . . . .
C4 C 0.566(4) 0.3977(19) 0.3549(3) 0.033(3) Uani 1 1 d . . . . .
C5 C 0.483(4) 0.421(2) 0.3235(4) 0.036(4) Uani 1 1 d . . . . .
H5A H 0.359209 0.538676 0.317296 0.043 Uiso 1 1 calc R U . . .
C6 C 0.728(5) 0.220(2) 0.3641(3) 0.033(3) Uani 1 1 d . . . . .
C7 C 0.727(6) 0.423(3) 0.4740(4) 0.055(5) Uani 1 1 d . . . . .
H7A H 0.783956 0.387974 0.493959 0.065 Uiso 1 1 calc R U . . .
C8 C 0.764(4) 0.099(2) 0.3117(3) 0.032(3) Uani 1 1 d . . . . .
C9 C 0.807(5) 0.288(2) 0.4506(3) 0.045(4) Uani 1 1 d . . . . .
H9A H 0.916535 0.160313 0.454953 0.054 Uiso 1 1 calc R U . . .
C10 C 0.841(4) 0.069(2) 0.3422(4) 0.036(4) Uani 1 1 d . . . . .
H10A H 0.963914 -0.049035 0.348246 0.043 Uiso 1 1 calc R U . . .
C11 C 0.841(4) 0.182(2) 0.3961(3) 0.035(4) Uani 1 1 d . . . . .
C12 C 0.560(5) 0.612(3) 0.4679(4) 0.052(4) Uani 1 1 d . . . . .
H12A H 0.514139 0.707458 0.483720 0.062 Uiso 1 1 calc R U . . .
C13 C 0.460(5) 0.662(2) 0.4380(4) 0.051(4) Uani 1 1 d . . . . .
H13A H 0.334528 0.783049 0.433962 0.061 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
I1 C8 2.101(13) . ?
S1 C4 1.731(14) . ?
S1 C1 1.759(15) . ?
O1 C11 1.204(18) . ?
C1 C13 1.38(2) . ?
C1 C3 1.40(2) . ?
C2 C5 1.35(2) . ?
C2 C8 1.39(2) . ?
C2 H2A 0.9300 . ?
C3 C9 1.39(2) . ?
C3 C11 1.50(2) . ?
C4 C6 1.35(2) . ?
C4 C5 1.43(2) . ?
C5 H5A 0.9300 . ?
C6 C10 1.42(2) . ?
C6 C11 1.50(2) . ?
C7 C9 1.36(2) . ?
C7 C12 1.39(3) . ?
C7 H7A 0.9300 . ?
C8 C10 1.38(2) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C12 C13 1.41(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 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
C4 S1 C1 103.4(7) . . ?
C13 C1 C3 122.4(14) . . ?
C13 C1 S1 114.0(12) . . ?
C3 C1 S1 123.6(11) . . ?
C5 C2 C8 119.5(13) . . ?
C5 C2 H2A 120.3 . . ?
C8 C2 H2A 120.3 . . ?
C9 C3 C1 117.8(13) . . ?
C9 C3 C11 118.1(13) . . ?
C1 C3 C11 124.1(12) . . ?
C6 C4 C5 119.5(12) . . ?
C6 C4 S1 126.0(11) . . ?
C5 C4 S1 114.4(10) . . ?
C2 C5 C4 120.8(13) . . ?
C2 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C4 C6 C10 120.1(13) . . ?
C4 C6 C11 124.3(13) . . ?
C10 C6 C11 115.1(13) . . ?
C9 C7 C12 119.6(16) . . ?
C9 C7 H7A 120.2 . . ?
C12 C7 H7A 120.2 . . ?
C2 C8 C10 120.9(13) . . ?
C2 C8 I1 118.9(10) . . ?
C10 C8 I1 120.1(10) . . ?
C7 C9 C3 121.8(15) . . ?
C7 C9 H9A 119.1 . . ?
C3 C9 H9A 119.1 . . ?
C8 C10 C6 119.0(13) . . ?
C8 C10 H10A 120.5 . . ?
C6 C10 H10A 120.5 . . ?
O1 C11 C6 121.8(13) . . ?
O1 C11 C3 120.0(13) . . ?
C6 C11 C3 118.1(12) . . ?
C7 C12 C13 120.9(15) . . ?
C7 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C1 C13 C12 117.4(16) . . ?
C1 C13 H13A 121.3 . . ?
C12 C13 H13A 121.3 . . ?

_refine_diff_density_max         1.650
_refine_diff_density_min         -1.309
_refine_diff_density_rms         0.273


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_preparation       Luminescent
