# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_160314-syn-MeS-BDT
_database_code_depnum_ccdc_archive 'CCDC 1558838'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H10 S4'
_chemical_formula_moiety         'C12 H10 S4'
_chemical_formula_weight         282.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.6642(3)
_cell_length_b                   5.65404(18)
_cell_length_c                   11.1188(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.6704(19)
_cell_angle_gamma                90.0000
_cell_volume                     607.30(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7247
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      68.18
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292.00
_exptl_absorpt_coefficient_mu    6.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.933

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10083
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_min         4.577
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1110
_reflns_number_gt                973
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1088
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1110
_refine_ls_number_parameters     74
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0703P)²+0.0418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0104(17)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.74202(6) 0.26453(9) 0.37780(5) 0.0447(3) Uani 1 1 d . . . . .
S2 S 0.60362(6) 0.49959(10) 0.16800(5) 0.0481(3) Uani 1 1 d . . . . .
C1 C 0.7392(2) 0.5001(3) 0.27521(19) 0.0382(5) Uani 1 1 d . . . . .
C2 C 1.0464(2) 0.7135(4) 0.4461(2) 0.0403(5) Uani 1 1 d . . . . .
H2 H 1.0783 0.8557 0.4108 0.048 Uiso 1 1 calc R U . . .
C3 C 0.9320(2) 0.5926(4) 0.39689(17) 0.0373(5) Uani 1 1 d . . . . .
C4 C 0.8447(2) 0.6564(4) 0.29477(18) 0.0396(5) Uani 1 1 d . . . . .
H4 H 0.8591 0.7924 0.2465 0.048 Uiso 1 1 calc R U . . .
C5 C 0.88827(19) 0.3797(4) 0.45247(18) 0.0370(5) Uani 1 1 d . . . . .
C6 C 0.6407(3) 0.7635(4) 0.0855(2) 0.0549(7) Uani 1 1 d . . . . .
H6A H 0.5707 0.7849 0.0209 0.066 Uiso 1 1 calc R U . . .
H6B H 0.6394 0.8999 0.1398 0.066 Uiso 1 1 calc R U . . .
H6C H 0.7324 0.7499 0.0507 0.066 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.744(2) . ?
S1 C1 1.753(2) . ?
S2 C1 1.746(2) . ?
S2 C6 1.793(2) . ?
C1 C4 1.362(3) . ?
C2 C5 1.380(3) 3_766 ?
C2 C3 1.398(3) . ?
C2 H2 0.9500 . ?
C3 C5 1.423(3) . ?
C3 C4 1.441(3) . ?
C4 H4 0.9500 . ?
C5 C2 1.380(3) 3_766 ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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
C5 S1 C1 91.31(10) . . ?
C1 S2 C6 100.99(11) . . ?
C4 C1 S2 130.81(17) . . ?
C4 C1 S1 113.08(16) . . ?
S2 C1 S1 116.11(12) . . ?
C5 C2 C3 118.1(2) 3_766 . ?
C5 C2 H2 121.0 3_766 . ?
C3 C2 H2 121.0 . . ?
C2 C3 C5 119.01(18) . . ?
C2 C3 C4 128.6(2) . . ?
C5 C3 C4 112.33(17) . . ?
C1 C4 C3 112.42(19) . . ?
C1 C4 H4 123.8 . . ?
C3 C4 H4 123.8 . . ?
C2 C5 C3 122.89(18) 3_766 . ?
C2 C5 S1 126.24(17) 3_766 . ?
C3 C5 S1 110.84(15) . . ?
S2 C6 H6A 109.5 . . ?
S2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
C6 S2 C1 C4 0.9(2) . . . . ?
C6 S2 C1 S1 179.87(13) . . . . ?
C5 S1 C1 C4 0.97(17) . . . . ?
C5 S1 C1 S2 -178.17(12) . . . . ?
C5 C2 C3 C5 -0.3(3) 3_766 . . . ?
C5 C2 C3 C4 177.99(19) 3_766 . . . ?
S2 C1 C4 C3 177.89(15) . . . . ?
S1 C1 C4 C3 -1.1(2) . . . . ?
C2 C3 C4 C1 -177.7(2) . . . . ?
C5 C3 C4 C1 0.6(3) . . . . ?
C2 C3 C5 C2 0.3(3) . . . 3_766 ?
C4 C3 C5 C2 -178.25(18) . . . 3_766 ?
C2 C3 C5 S1 178.63(15) . . . . ?
C4 C3 C5 S1 0.1(2) . . . . ?
C1 S1 C5 C2 177.70(19) . . . 3_766 ?
C1 S1 C5 C3 -0.58(16) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_160316-anti-MeS-BDT
_database_code_depnum_ccdc_archive 'CCDC 1558840'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H10 S4'
_chemical_formula_moiety         'C12 H10 S4'
_chemical_formula_weight         282.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.37267(18)
_cell_length_b                   13.9725(3)
_cell_length_c                   5.34146(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.3620(13)
_cell_angle_gamma                90.0000
_cell_volume                     616.56(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5660
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    98
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292.00
_exptl_absorpt_coefficient_mu    6.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_T_max  0.507

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      98
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10747
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_min         5.355
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1126
_reflns_number_gt                1028
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0908
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1126
_refine_ls_number_parameters     74
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0659P)²+0.0625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0165(17)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.12182(5) 0.15738(3) 0.10276(9) 0.0338(2) Uani 1 1 d . . . . .
S2 S 0.37898(5) 0.07712(3) 0.14680(9) 0.0382(2) Uani 1 1 d . . . . .
C3 C 0.16576(19) -0.02690(12) 0.5154(3) 0.0304(4) Uani 1 1 d . . . . .
H3 H 0.2759 -0.0453 0.5259 0.036 Uiso 1 1 calc R U . . .
C4 C -0.0665(2) 0.06953(11) 0.3321(3) 0.0294(4) Uani 1 1 d . . . . .
C5 C 0.1756(2) 0.09804(12) 0.1668(3) 0.0303(4) Uani 1 1 d . . . . .
C6 C 0.4105(2) 0.15621(14) -0.1061(4) 0.0408(5) Uani 1 1 d . . . . .
H6A H 0.5227 0.1507 -0.1354 0.049 Uiso 1 1 calc R U . . .
H6B H 0.3368 0.1388 -0.2612 0.049 Uiso 1 1 calc R U . . .
H6C H 0.3892 0.2223 -0.0595 0.049 Uiso 1 1 calc R U . . .
C7 C 0.09852(19) 0.04382(11) 0.3465(3) 0.0285(4) Uani 1 1 d . . . . .
C8 C 0.0721(2) 0.15994(12) 0.0284(4) 0.0339(4) Uani 1 1 d . . . . .
H8 H 0.1029 0.2009 -0.0974 0.041 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.7333(18) . ?
S1 C4 1.7427(17) . ?
S2 C5 1.7484(17) . ?
S2 C6 1.798(2) . ?
C3 C4 1.389(2) 3_556 ?
C3 C7 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C3 1.389(2) 3_556 ?
C4 C7 1.418(2) . ?
C5 C8 1.355(2) . ?
C5 C7 1.454(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8 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
C8 S1 C4 91.37(8) . . ?
C5 S2 C6 101.92(9) . . ?
C4 C3 C7 117.82(15) 3_556 . ?
C4 C3 H3 121.1 3_556 . ?
C7 C3 H3 121.1 . . ?
C3 C4 C7 122.03(16) 3_556 . ?
C3 C4 S1 126.77(13) 3_556 . ?
C7 C4 S1 111.20(13) . . ?
C8 C5 C7 112.32(16) . . ?
C8 C5 S2 128.03(15) . . ?
C7 C5 S2 119.64(13) . . ?
S2 C6 H6A 109.5 . . ?
S2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 C4 120.15(15) . . ?
C3 C7 C5 128.40(15) . . ?
C4 C7 C5 111.44(15) . . ?
C5 C8 S1 113.67(14) . . ?
C5 C8 H8 123.2 . . ?
S1 C8 H8 123.2 . . ?

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
C8 S1 C4 C3 -179.58(16) . . . 3_556 ?
C8 S1 C4 C7 -0.18(13) . . . . ?
C6 S2 C5 C8 -1.26(19) . . . . ?
C6 S2 C5 C7 177.50(14) . . . . ?
C4 C3 C7 C4 -0.7(3) 3_556 . . . ?
C4 C3 C7 C5 -179.37(16) 3_556 . . . ?
C3 C4 C7 C3 0.7(3) 3_556 . . . ?
S1 C4 C7 C3 -178.73(13) . . . . ?
C3 C4 C7 C5 179.60(15) 3_556 . . . ?
S1 C4 C7 C5 0.18(18) . . . . ?
C8 C5 C7 C3 178.73(18) . . . . ?
S2 C5 C7 C3 -0.2(2) . . . . ?
C8 C5 C7 C4 -0.1(2) . . . . ?
S2 C5 C7 C4 -179.02(12) . . . . ?
C7 C5 C8 S1 -0.1(2) . . . . ?
S2 C5 C8 S1 178.77(10) . . . . ?
C4 S1 C8 C5 0.15(15) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_170322-alfa-MT-BDT-by-PVT
_database_code_depnum_ccdc_archive 'CCDC 1558839'
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-08-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H10 S4'
_chemical_formula_moiety         'C12 H10 S4'
_chemical_formula_weight         282.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.82323(18)
_cell_length_b                   7.7052(3)
_cell_length_c                   14.0680(5)
_cell_angle_alpha                78.199(2)
_cell_angle_beta                 84.6910(18)
_cell_angle_gamma                88.4900(19)
_cell_volume                     615.21(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3238
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292.00
_exptl_absorpt_coefficient_mu    6.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.934

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            11237
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         3.222
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2218
_reflns_number_gt                1351
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0961
_refine_ls_wR_factor_ref         0.3803
_refine_ls_wR_factor_gt          0.2904
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2218
_refine_ls_number_parameters     145
_refine_ls_goodness_of_fit_ref   1.456
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.22
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.2611(3) -0.4340(3) 1.17109(14) 0.0641(8) Uani 1 1 d . . . . .
S2 S 0.7572(3) -0.1219(3) 1.18527(15) 0.0686(8) Uani 1 1 d . . . . .
S3 S 1.0350(4) -0.5664(3) 1.37609(14) 0.0749(8) Uani 1 1 d . . . . .
S4 S 0.5325(4) -0.0414(3) 1.37458(15) 0.0813(9) Uani 1 1 d . . . . .
C5 C 0.8488(11) -0.6141(7) 1.2068(4) 0.0420(14) Uani 1 1 d . . . . .
H5 H 0.7175 -0.6744 1.2378 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3425(11) 0.0548(7) 1.1973(4) 0.0396(13) Uani 1 1 d . . . . .
H6 H 0.2107 0.1082 1.2214 0.047 Uiso 1 1 calc R U . . .
C7 C 0.7851(11) -0.5910(8) 1.0251(5) 0.0495(16) Uani 1 1 d . . . . .
H7 H 0.6439 -0.6482 1.0405 0.059 Uiso 1 1 calc R U . . .
C8 C 0.7182(11) -0.0885(9) 0.9881(5) 0.0529(17) Uani 1 1 d . . . . .
H8 H 0.8593 -0.1460 0.9809 0.063 Uiso 1 1 calc R U . . .
C9 C 1.1273(10) -0.4652(8) 1.0712(5) 0.0455(14) Uani 1 1 d . . . . .
C10 C 1.0434(11) -0.5487(9) 1.2523(5) 0.0517(16) Uani 1 1 d . . . . .
C11 C 0.4129(11) 0.0282(8) 1.0915(5) 0.0481(15) Uani 1 1 d . . . . .
C12 C 0.6273(10) -0.0581(8) 1.0774(5) 0.0459(15) Uani 1 1 d . . . . .
C13 C 0.5381(12) -0.0264(9) 1.2488(5) 0.0548(17) Uani 1 1 d . . . . .
C14 C 0.9161(10) -0.5590(7) 1.0985(5) 0.0463(15) Uani 1 1 d . . . . .
C15 C 1.3252(18) -0.5408(15) 1.3953(6) 0.091(3) Uani 1 1 d . . . . .
H15A H 1.3384 -0.5488 1.4636 0.109 Uiso 1 1 calc R U . . .
H15B H 1.4169 -0.6325 1.3731 0.109 Uiso 1 1 calc R U . . .
H15C H 1.3786 -0.4271 1.3597 0.109 Uiso 1 1 calc R U . . .
C16 C 0.8262(17) -0.0598(15) 1.3977(6) 0.089(3) Uani 1 1 d . . . . .
H16A H 0.8386 -0.0688 1.4661 0.107 Uiso 1 1 calc R U . . .
H16B H 0.8922 -0.1638 1.3780 0.107 Uiso 1 1 calc R U . . .
H16C H 0.9073 0.0432 1.3616 0.107 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C9 1.730(6) . ?
S1 C10 1.753(7) . ?
S2 C13 1.725(7) . ?
S2 C12 1.733(6) . ?
S3 C10 1.715(7) . ?
S3 C15 1.758(10) . ?
S4 C13 1.747(7) . ?
S4 C16 1.767(10) . ?
C5 C10 1.498(8) . ?
C5 C14 1.513(8) . ?
C5 H5 0.9300 . ?
C6 C13 1.464(9) . ?
C6 C11 1.559(8) . ?
C6 H6 0.9300 . ?
C7 C9 1.388(9) 2_747 ?
C7 C14 1.403(8) . ?
C7 H7 0.9300 . ?
C8 C12 1.380(9) . ?
C8 C11 1.408(9) 2_657 ?
C8 H8 0.9300 . ?
C9 C7 1.388(9) 2_747 ?
C9 C14 1.424(8) . ?
C11 C8 1.408(9) 2_657 ?
C11 C12 1.416(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C9 S1 C10 91.8(3) . . ?
C13 S2 C12 91.6(3) . . ?
C10 S3 C15 103.2(4) . . ?
C13 S4 C16 104.1(4) . . ?
C10 C5 C14 103.7(5) . . ?
C10 C5 H5 128.1 . . ?
C14 C5 H5 128.1 . . ?
C13 C6 C11 101.7(5) . . ?
C13 C6 H6 129.1 . . ?
C11 C6 H6 129.1 . . ?
C9 C7 C14 118.0(6) 2_747 . ?
C9 C7 H7 121.0 2_747 . ?
C14 C7 H7 121.0 . . ?
C12 C8 C11 116.8(6) . 2_657 ?
C12 C8 H8 121.6 . . ?
C11 C8 H8 121.6 2_657 . ?
C7 C9 C14 123.0(6) 2_747 . ?
C7 C9 S1 124.6(5) 2_747 . ?
C14 C9 S1 112.4(5) . . ?
C5 C10 S3 121.1(5) . . ?
C5 C10 S1 115.9(5) . . ?
S3 C10 S1 122.6(4) . . ?
C8 C11 C12 119.9(6) 2_657 . ?
C8 C11 C6 124.3(6) 2_657 . ?
C12 C11 C6 115.8(6) . . ?
C8 C12 C11 123.4(6) . . ?
C8 C12 S2 124.7(5) . . ?
C11 C12 S2 111.9(5) . . ?
C6 C13 S2 118.9(5) . . ?
C6 C13 S4 119.4(5) . . ?
S2 C13 S4 121.5(4) . . ?
C7 C14 C9 118.9(6) . . ?
C7 C14 C5 124.9(5) . . ?
C9 C14 C5 116.1(5) . . ?
S3 C15 H15A 109.5 . . ?
S3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S4 C16 H16A 109.5 . . ?
S4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C10 S1 C9 C7 -177.8(6) . . . 2_747 ?
C10 S1 C9 C14 1.2(5) . . . . ?
C14 C5 C10 S3 175.2(4) . . . . ?
C14 C5 C10 S1 1.7(6) . . . . ?
C15 S3 C10 C5 161.9(6) . . . . ?
C15 S3 C10 S1 -25.0(6) . . . . ?
C9 S1 C10 C5 -1.7(5) . . . . ?
C9 S1 C10 S3 -175.1(4) . . . . ?
C13 C6 C11 C8 -178.4(6) . . . 2_657 ?
C13 C6 C11 C12 -0.3(7) . . . . ?
C11 C8 C12 C11 0.3(10) 2_657 . . . ?
C11 C8 C12 S2 179.5(5) 2_657 . . . ?
C8 C11 C12 C8 -0.3(11) 2_657 . . . ?
C6 C11 C12 C8 -178.4(5) . . . . ?
C8 C11 C12 S2 -179.6(5) 2_657 . . . ?
C6 C11 C12 S2 2.3(7) . . . . ?
C13 S2 C12 C8 178.0(6) . . . . ?
C13 S2 C12 C11 -2.7(5) . . . . ?
C11 C6 C13 S2 -1.8(6) . . . . ?
C11 C6 C13 S4 -176.3(4) . . . . ?
C12 S2 C13 C6 2.8(5) . . . . ?
C12 S2 C13 S4 177.1(4) . . . . ?
C16 S4 C13 C6 -157.3(6) . . . . ?
C16 S4 C13 S2 28.3(6) . . . . ?
C9 C7 C14 C9 2.3(10) 2_747 . . . ?
C9 C7 C14 C5 -178.8(5) 2_747 . . . ?
C7 C9 C14 C7 -2.4(10) 2_747 . . . ?
S1 C9 C14 C7 178.7(4) . . . . ?
C7 C9 C14 C5 178.6(6) 2_747 . . . ?
S1 C9 C14 C5 -0.4(7) . . . . ?
C10 C5 C14 C7 -179.8(6) . . . . ?
C10 C5 C14 C9 -0.8(6) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


