# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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#  from this site to visualise CIF-encoded structures and 
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#
data_cmpnd1
# start Validation Reply Form
_vrf_PLAT911_cmpnd1              
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.595        411   
RESPONSE: Weaker high angle data were omitted (OMIT -3 50) as well as
a small number (16) of reflections with strong disagreement between
Fo and Fc in the final stages of refinement. These were likely 
associated with deficiencies in the disorder model. 
;
_vrf_PLAT088_cmpnd1              
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.96        
RESPONSE: The structure was severely disordered over 2 sites in a 4:1
ratio. Substantial numbers of restraints (302) were applied to model 
the low intensity data associated with the light atoms in the minor
component, affording a poor data:parameter ratio. 
;
_vrf_PLAT042_cmpnd1              
;
PROBLEM: Calc and reported Moietyformula strings differ   
RESPONSE: The crystal comprises both dimeric and monomeric forms of
C13H7S4N in an approximate 80:40 ratio. The moiety formula string 
offered by the authors is more meaningful (based on Z = 8, ie 8 monomers
of which 80% are dimerised) than the one calculated which is based on Z =3
and which has no relationship to the monoclinic symmetry.
;

_vrf_PLAT002_cmpnd1              
;
PROBLEM: Number of Distance or angle Restraints on AtSite    48 Note   
RESPONSE: The structure is substantially disordered, comprising a dimer
(sof = 0.80) and two monomers (sof = 0.20 each). Whilst the minor
component (esp S atoms) was clearly evident in the differnece map,
the low electron density associated with the minor component of the
disorder required mulptiple restraints for both the geometry and thermal
elipsoids, particularly for the lighter atoms.  
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '0.8(C26 H14 N2 S8), 0.4 (C13 H7 N S4)'
_chemical_formula_sum            'C13 H7 N S4'
_chemical_formula_weight         305.44

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'
S S 0.1246 0.1234 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.274(2)
_cell_length_b                   8.2761(17)
_cell_length_c                   27.958(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.47(3)
_cell_angle_gamma                90
_cell_volume                     2596.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    50685
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.709
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related equivalents
Sortv (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'thin slice omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12885
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.864
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.888
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.888
_reflns_number_total             4165
_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       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_refine_special_details          
;
The structure was solved by direct methods to reveal a severely disordered
structure which was refined as the [2+2] cycloaddition dimer and two 
crystallographically independent monomers. The site occupancies were
initially refined using common U(iso) for chemically equivalent atoms to
afford a 0.80:0.0 ratio of dimer to monomer components. These were then
fixed in the latter stages of refinement.
All non-H atoms associated with the major (dimer) component were refined 
anisotropically. For the monomer components refinement was more complex.
One H2C4S2 component appeared coincident with a fragment of the dimer
and was constrained to have identical coordinates and displacement
parameters as the fragment of the dimer component (EXYZ, EADP).
For the remaining atoms of the minor component, sufficient electron density
was associated with the S atom positions to permit anisotropic refinement
with U(ij) tied to the equivalent major component of the disorder.
Conversely the lighter C and N atoms were refined isotropically with geometric
and thermal restraints (SAME and SIMU) to the geometry of equivalent fragments
in the main component of disorder. This approach gave a generally acceptable
refinement but a small number (16) of highly disagreeable reflections (with
|Fo-Fc| > 5.5 esds).These reflections were omitted in the final cycles of
least squares to afford a final R1 = 8.7% and residual electron density < 
0.32e.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+14.2266P] 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
_refine_ls_extinction_coef       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4165
_refine_ls_number_parameters     465
_refine_ls_number_restraints     302
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1718
_refine_ls_goodness_of_fit_ref   1.260
_refine_ls_restrained_S_all      1.223
_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
C14 C 0.6636(11) 0.2325(16) 0.0687(4) 0.058(3) Uani 0.8 1 d D U P A 1
H14 H 0.6480 0.1507 0.0451 0.070 Uiso 0.8 1 calc R U P A 1
C15 C 0.7479(11) 0.336(2) 0.0652(4) 0.064(3) Uani 0.8 1 d D U P A 1
H15 H 0.7969 0.3310 0.0394 0.077 Uiso 0.8 1 calc R U P A 1
S7 S 0.5789(3) 0.2451(4) 0.11740(10) 0.0449(7) Uani 0.8 1 d D U P A 1
S8 S 0.7692(3) 0.4858(4) 0.10927(12) 0.0496(8) Uani 0.8 1 d D U P A 1
C16 C 0.6582(8) 0.4129(11) 0.1449(4) 0.0346(19) Uani 0.8 1 d D U P A 1
C17 C 0.6396(8) 0.4711(10) 0.1877(3) 0.0291(18) Uani 0.8 1 d D U P A 1
S3 S 0.5352(4) 0.3849(5) 0.22214(15) 0.0345(9) Uani 0.8 1 d D U P A 1
S5 S 0.7329(3) 0.6187(4) 0.21563(11) 0.0366(7) Uani 0.8 1 d D U P A 1
C19 C 0.5482(7) 0.5256(10) 0.2726(3) 0.0288(16) Uani 0.8 1 d . U P A 1
C18 C 0.6481(8) 0.6522(10) 0.2664(3) 0.0315(17) Uani 0.8 1 d . U P A 1
H18 H 0.7029 0.6599 0.2966 0.038 Uiso 0.8 1 calc R U P A 1
C20 C 0.4646(10) 0.3173(15) 0.3221(4) 0.053(3) Uani 0.8 1 d D U P A 1
H20 H 0.4110 0.2950 0.2946 0.064 Uiso 0.8 1 calc R U P A 1
C23 C 0.4499(9) 0.2391(16) 0.3645(3) 0.054(3) Uani 0.8 1 d D U P A 1
H23 H 0.3908 0.1578 0.3657 0.065 Uiso 0.8 1 calc R U P A 1
C24 C 0.5218(9) 0.2799(14) 0.4055(3) 0.050(2) Uani 0.8 1 d D U P A 1
C25 C 0.6132(9) 0.3902(15) 0.4015(3) 0.055(3) Uani 0.8 1 d D U P A 1
H25 H 0.6658 0.4154 0.4291 0.067 Uiso 0.8 1 calc R U P A 1
C22 C 0.6293(9) 0.4644(14) 0.3579(3) 0.044(3) Uani 0.8 1 d D U P A 1
H22 H 0.6914 0.5407 0.3555 0.053 Uiso 0.8 1 calc R U P A 1
C21 C 0.5534(8) 0.4248(11) 0.3185(3) 0.031(2) Uani 0.8 1 d D U P A 1
C26 C 0.4964(11) 0.2127(18) 0.4513(4) 0.076(4) Uani 0.8 1 d D U P A 1
N1 N 0.4774(13) 0.163(2) 0.4869(3) 0.144(7) Uani 0.8 1 d D U P A 1
C2 C 0.4870(8) 0.6847(11) 0.0494(3) 0.057(2) Uani 0.8 1 d . U P A 1
H2 H 0.5219 0.6922 0.0198 0.068 Uiso 0.8 1 calc R U P A 1
C1 C 0.4016(8) 0.5800(12) 0.0556(3) 0.063(2) Uani 0.8 1 d . U P A 1
H1 H 0.3714 0.5116 0.0299 0.075 Uiso 0.8 1 calc R U P A 1
S4 S 0.53220(18) 0.8081(3) 0.09788(7) 0.0480(5) Uani 0.8 1 d . U P A 1
S6 S 0.34518(19) 0.5686(3) 0.11090(7) 0.0531(6) Uani 0.8 1 d . U P A 1
C3 C 0.4381(6) 0.7217(9) 0.1368(2) 0.0381(15) Uani 0.8 1 d . U P A 1
C4 C 0.4360(6) 0.7647(8) 0.1833(2) 0.0368(15) Uani 0.8 1 d . U P A 1
S1 S 0.3395(9) 0.6776(12) 0.2201(3) 0.0332(13) Uani 0.8 1 d . U P A 1
C6 C 0.4506(7) 0.6748(10) 0.2715(3) 0.0317(16) Uani 0.8 1 d . U P A 1
C5 C 0.5547(8) 0.7944(10) 0.2641(3) 0.0346(18) Uani 0.8 1 d . U P A 1
H5 H 0.5703 0.8659 0.2928 0.041 Uiso 0.8 1 calc R U P A 1
S2 S 0.5280(9) 0.9104(9) 0.2125(3) 0.0365(10) Uani 0.8 1 d . U P A 1
C7 C 0.3859(7) 0.6882(11) 0.3168(3) 0.0335(18) Uani 0.8 1 d D U P A 1
C8 C 0.2799(8) 0.6090(12) 0.3207(3) 0.047(3) Uani 0.8 1 d D U P A 1
H8 H 0.2405 0.5594 0.2930 0.057 Uiso 0.8 1 calc R U P A 1
C9 C 0.2289(9) 0.5994(13) 0.3637(3) 0.046(3) Uani 0.8 1 d D U P A 1
H9 H 0.1560 0.5432 0.3656 0.055 Uiso 0.8 1 calc R U P A 1
C10 C 0.2868(10) 0.6739(15) 0.4040(4) 0.043(3) Uani 0.8 1 d D U P A 1
C11 C 0.3895(9) 0.7578(16) 0.4015(4) 0.056(3) Uani 0.8 1 d D U P A 1
H11 H 0.4260 0.8130 0.4288 0.068 Uiso 0.8 1 calc R U P A 1
C12 C 0.4402(9) 0.7610(14) 0.3581(3) 0.047(3) Uani 0.8 1 d D U P A 1
H12 H 0.5142 0.8147 0.3565 0.057 Uiso 0.8 1 calc R U P A 1
C13 C 0.2345(12) 0.662(2) 0.4500(4) 0.052(3) Uani 0.8 1 d D U P A 1
N2 N 0.1950(13) 0.643(2) 0.4854(4) 0.075(4) Uani 0.8 1 d D U P A 1
C14A C 0.672(4) 0.180(5) 0.0571(14) 0.050(14) Uiso 0.2 1 d D . P B 2
H14A H 0.6616 0.0845 0.0382 0.060 Uiso 0.2 1 calc R U P B 2
C15A C 0.751(3) 0.286(4) 0.0487(12) 0.039(11) Uiso 0.2 1 d D . P B 2
H15A H 0.8008 0.2694 0.0236 0.047 Uiso 0.2 1 calc R U P B 2
S7A S 0.5865(16) 0.218(2) 0.1038(5) 0.0449(7) Uani 0.2 1 d D . P B 2
S8A S 0.7653(10) 0.4597(18) 0.0842(5) 0.052(4) Uani 0.2 1 d D . P B 2
C16A C 0.669(3) 0.390(4) 0.1273(9) 0.026(10) Uiso 0.2 1 d D . P B 2
C17A C 0.663(3) 0.445(3) 0.1716(8) 0.016(8) Uiso 0.2 1 d D . P B 2
S3A S 0.5666(14) 0.3649(19) 0.2100(5) 0.030(3) Uani 0.2 1 d D . P B 2
S5A S 0.7459(10) 0.6140(14) 0.1934(4) 0.032(3) Uani 0.2 1 d D . P B 2
C19A C 0.624(3) 0.472(4) 0.2610(10) 0.024(6) Uiso 0.2 1 d . . P B 2
C18A C 0.705(4) 0.584(5) 0.2542(14) 0.044(9) Uiso 0.2 1 d . . P B 2
H18A H 0.7401 0.6465 0.2802 0.053 Uiso 0.2 1 calc R U P B 2
C20A C 0.484(3) 0.343(5) 0.3118(11) 0.034(11) Uiso 0.2 1 d D U P B 2
H20A H 0.4432 0.2974 0.2836 0.041 Uiso 0.2 1 calc R U P B 2
C23A C 0.445(3) 0.307(5) 0.3555(9) 0.050(12) Uiso 0.2 1 d D U P B 2
H23A H 0.3768 0.2400 0.3571 0.060 Uiso 0.2 1 calc R U P B 2
C24A C 0.503(3) 0.367(5) 0.3973(10) 0.057(11) Uiso 0.2 1 d D U P B 2
C25A C 0.602(3) 0.464(5) 0.3932(11) 0.048(12) Uiso 0.2 1 d D U P B 2
H25A H 0.6467 0.5025 0.4215 0.058 Uiso 0.2 1 calc R U P B 2
C22A C 0.637(4) 0.505(5) 0.3484(13) 0.073(17) Uiso 0.2 1 d D U P B 2
H22A H 0.7023 0.5766 0.3460 0.088 Uiso 0.2 1 calc R U P B 2
C21A C 0.578(3) 0.441(4) 0.3075(11) 0.024(10) Uiso 0.2 1 d D U P B 2
C26A C 0.462(3) 0.328(5) 0.4434(10) 0.056(10) Uiso 0.2 1 d D U P B 2
N1A N 0.432(4) 0.302(6) 0.4797(11) 0.094(15) Uiso 0.2 1 d D U P B 2
C2A C 0.4870(8) 0.6847(11) 0.0494(3) 0.057(2) Uani 0.2 1 d . U P C 2
H2A H 0.5219 0.6922 0.0198 0.068 Uiso 0.2 1 calc R U P C 2
C1A C 0.4016(8) 0.5800(12) 0.0556(3) 0.063(2) Uani 0.2 1 d . U P C 2
H1A H 0.3714 0.5116 0.0299 0.075 Uiso 0.2 1 calc R U P C 2
S4A S 0.53220(18) 0.8081(3) 0.09788(7) 0.0480(5) Uani 0.2 1 d . U P C 2
S6A S 0.34518(19) 0.5686(3) 0.11090(7) 0.0531(6) Uani 0.2 1 d . U P C 2
C3A C 0.4381(6) 0.7217(9) 0.1368(2) 0.0381(15) Uani 0.2 1 d . U P C 2
C4A C 0.4360(6) 0.7647(8) 0.1833(2) 0.0368(15) Uani 0.2 1 d . U P C 2
S1A S 0.350(4) 0.680(6) 0.2313(11) 0.043(8) Uani 0.2 1 d . U P C 2
C6A C 0.402(3) 0.789(4) 0.2806(12) 0.037(8) Uiso 0.2 1 d . . P C 2
C5A C 0.482(3) 0.906(4) 0.2720(10) 0.025(6) Uiso 0.2 1 d . . P C 2
H5A H 0.5122 0.9753 0.2975 0.030 Uiso 0.2 1 calc R U P C 2
S2A S 0.535(4) 0.935(5) 0.2076(16) 0.0365(10) Uani 0.2 1 d . U P C 2
C7A C 0.357(2) 0.755(3) 0.3272(8) 0.012(6) Uiso 0.2 1 d D U P C 2
C8A C 0.255(2) 0.666(3) 0.3288(10) 0.030(9) Uiso 0.2 1 d D U P C 2
H8A H 0.2150 0.6268 0.2997 0.036 Uiso 0.2 1 calc R U P C 2
C9A C 0.210(3) 0.633(4) 0.3717(9) 0.031(11) Uiso 0.2 1 d D U P C 2
H9A H 0.1387 0.5718 0.3722 0.037 Uiso 0.2 1 calc R U P C 2
C10A C 0.269(3) 0.690(5) 0.4145(10) 0.020(10) Uiso 0.2 1 d D U P C 2
C11A C 0.369(3) 0.780(5) 0.4140(10) 0.045(12) Uiso 0.2 1 d D U P C 2
H11A H 0.4072 0.8238 0.4430 0.054 Uiso 0.2 1 calc R U P C 2
C12A C 0.415(3) 0.809(4) 0.3706(10) 0.035(10) Uiso 0.2 1 d D U P C 2
H12A H 0.4878 0.8661 0.3704 0.041 Uiso 0.2 1 calc R U P C 2
C13A C 0.218(5) 0.655(8) 0.4597(14) 0.056(16) Uiso 0.2 1 d D U P C 2
N2A N 0.181(5) 0.625(7) 0.4947(12) 0.058(16) Uiso 0.2 1 d D U P C 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
C14 C15 1.290(15) . ?
C14 S7 1.739(10) . ?
C14 H14 0.9500 . ?
C15 S8 1.749(15) . ?
C15 H15 0.9500 . ?
S7 C16 1.785(10) . ?
S8 C16 1.778(9) . ?
C16 C17 1.325(14) . ?
C17 S3 1.744(9) . ?
C17 S5 1.748(8) . ?
S3 C19 1.824(8) . ?
S5 C18 1.806(9) . ?
C19 C21 1.528(12) . ?
C19 C18 1.561(11) . ?
C19 C6 1.652(11) . ?
C18 C5 1.576(12) . ?
C18 H18 1.0000 . ?
C20 C21 1.350(13) . ?
C20 C23 1.376(14) . ?
C20 H20 0.9500 . ?
C23 C24 1.379(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(13) . ?
C24 C26 1.450(13) . ?
C25 C22 1.392(13) . ?
C25 H25 0.9500 . ?
C22 C21 1.368(10) . ?
C22 H22 0.9500 . ?
C26 N1 1.117(13) . ?
C2 C1 1.319(12) . ?
C2 S4 1.735(8) . ?
C2 H2 0.9500 . ?
C1 S6 1.731(9) . ?
C1 H1 0.9500 . ?
S4 C3 1.744(7) . ?
S6 C3 1.757(8) . ?
C3 C4 1.349(9) . ?
C4 S1 1.726(11) . ?
C4 S2 1.742(12) . ?
S1 C6 1.815(12) . ?
C6 C7 1.525(11) . ?
C6 C5 1.565(11) . ?
C5 S2 1.735(10) . ?
C5 H5 1.0000 . ?
C7 C8 1.376(11) . ?
C7 C12 1.390(12) . ?
C8 C9 1.382(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(12) . ?
C9 H9 0.9500 . ?
C10 C11 1.358(12) . ?
C10 C13 1.468(15) . ?
C11 C12 1.391(12) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N2 1.134(14) . ?
C14A C15A 1.28(2) . ?
C14A S7A 1.73(2) . ?
C14A H14A 0.9500 . ?
C15A S8A 1.75(2) . ?
C15A H15A 0.9500 . ?
S7A C16A 1.795(18) . ?
S8A C16A 1.790(18) . ?
C16A C17A 1.33(2) . ?
C17A S3A 1.736(19) . ?
C17A S5A 1.753(17) . ?
S3A C19A 1.75(3) . ?
S5A C18A 1.82(4) . ?
C19A C18A 1.32(5) . ?
C19A C21A 1.47(4) . ?
C18A H18A 0.9500 . ?
C20A C21A 1.35(2) . ?
C20A C23A 1.37(2) . ?
C20A H20A 0.9500 . ?
C23A C24A 1.38(2) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.39(2) . ?
C24A C26A 1.45(2) . ?
C25A C22A 1.39(2) . ?
C25A H25A 0.9500 . ?
C22A C21A 1.37(2) . ?
C22A H22A 0.9500 . ?
C26A N1A 1.12(2) . ?
S1A C6A 1.70(5) . ?
C6A C5A 1.36(4) . ?
C6A C7A 1.47(4) . ?
C5A S2A 1.97(5) . ?
C5A H5A 0.9500 . ?
C7A C8A 1.365(19) . ?
C7A C12A 1.40(2) . ?
C8A C9A 1.377(19) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.395(19) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.356(19) . ?
C10A C13A 1.46(2) . ?
C11A C12A 1.38(2) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A N2A 1.13(2) . ?

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
C15 C14 S7 118.9(11) . . ?
C15 C14 H14 120.5 . . ?
S7 C14 H14 120.5 . . ?
C14 C15 S8 118.0(10) . . ?
C14 C15 H15 121.0 . . ?
S8 C15 H15 121.0 . . ?
C14 S7 C16 95.4(5) . . ?
C15 S8 C16 95.6(5) . . ?
C17 C16 S8 124.2(7) . . ?
C17 C16 S7 123.7(7) . . ?
S8 C16 S7 112.0(6) . . ?
C16 C17 S3 121.6(6) . . ?
C16 C17 S5 121.2(7) . . ?
S3 C17 S5 116.6(6) . . ?
C17 S3 C19 99.1(4) . . ?
C17 S5 C18 96.8(4) . . ?
C21 C19 C18 119.3(7) . . ?
C21 C19 C6 113.2(6) . . ?
C18 C19 C6 89.0(6) . . ?
C21 C19 S3 107.2(6) . . ?
C18 C19 S3 110.4(5) . . ?
C6 C19 S3 117.4(5) . . ?
C19 C18 C5 91.1(6) . . ?
C19 C18 S5 115.2(6) . . ?
C5 C18 S5 119.0(5) . . ?
C19 C18 H18 110.1 . . ?
C5 C18 H18 110.1 . . ?
S5 C18 H18 110.1 . . ?
C21 C20 C23 121.7(8) . . ?
C21 C20 H20 119.2 . . ?
C23 C20 H20 119.2 . . ?
C20 C23 C24 119.4(10) . . ?
C20 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 118.4(9) . . ?
C23 C24 C26 119.3(10) . . ?
C25 C24 C26 122.2(9) . . ?
C24 C25 C22 121.3(8) . . ?
C24 C25 H25 119.4 . . ?
C22 C25 H25 119.4 . . ?
C21 C22 C25 118.4(10) . . ?
C21 C22 H22 120.8 . . ?
C25 C22 H22 120.8 . . ?
C20 C21 C22 120.6(10) . . ?
C20 C21 C19 116.9(8) . . ?
C22 C21 C19 121.1(9) . . ?
N1 C26 C24 179.0(16) . . ?
C1 C2 S4 116.6(6) . . ?
C1 C2 H2 121.7 . . ?
S4 C2 H2 121.7 . . ?
C2 C1 S6 119.2(7) . . ?
C2 C1 H1 120.4 . . ?
S6 C1 H1 120.4 . . ?
C2 S4 C3 95.5(4) . . ?
C1 S6 C3 94.3(4) . . ?
C4 C3 S4 124.1(6) . . ?
C4 C3 S6 121.5(5) . . ?
S4 C3 S6 114.3(4) . . ?
C3 C4 S1 122.3(7) . . ?
C3 C4 S2 124.7(6) . . ?
S1 C4 S2 113.0(6) . . ?
C4 S1 C6 92.9(6) . . ?
C7 C6 C5 119.3(7) . . ?
C7 C6 C19 114.3(6) . . ?
C5 C6 C19 88.2(6) . . ?
C7 C6 S1 107.9(6) . . ?
C5 C6 S1 110.9(6) . . ?
C19 C6 S1 115.6(6) . . ?
C6 C5 C18 91.7(6) . . ?
C6 C5 S2 112.9(6) . . ?
C18 C5 S2 120.6(7) . . ?
C6 C5 H5 110.1 . . ?
C18 C5 H5 110.1 . . ?
S2 C5 H5 110.1 . . ?
C5 S2 C4 93.1(4) . . ?
C8 C7 C12 117.3(8) . . ?
C8 C7 C6 121.2(7) . . ?
C12 C7 C6 120.8(8) . . ?
C7 C8 C9 122.1(8) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 118.5(9) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 121.4(10) . . ?
C11 C10 C13 119.6(9) . . ?
C9 C10 C13 119.0(9) . . ?
C10 C11 C12 118.6(9) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C7 C12 C11 122.0(8) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N2 C13 C10 175.5(16) . . ?
C15A C14A S7A 118(2) . . ?
C15A C14A H14A 121.2 . . ?
S7A C14A H14A 121.2 . . ?
C14A C15A S8A 119(2) . . ?
C14A C15A H15A 120.5 . . ?
S8A C15A H15A 120.5 . . ?
C14A S7A C16A 96.4(12) . . ?
C15A S8A C16A 95.0(12) . . ?
C17A C16A S8A 127.1(16) . . ?
C17A C16A S7A 123.0(15) . . ?
S8A C16A S7A 109.7(12) . . ?
C16A C17A S3A 122.3(14) . . ?
C16A C17A S5A 121.8(15) . . ?
S3A C17A S5A 115.8(13) . . ?
C17A S3A C19A 95.8(14) . . ?
C17A S5A C18A 92.4(15) . . ?
C18A C19A C21A 124(3) . . ?
C18A C19A S3A 116(3) . . ?
C21A C19A S3A 120(2) . . ?
C19A C18A S5A 118(3) . . ?
C19A C18A H18A 120.9 . . ?
S5A C18A H18A 120.9 . . ?
C21A C20A C23A 122(2) . . ?
C21A C20A H20A 119.0 . . ?
C23A C20A H20A 119.0 . . ?
C20A C23A C24A 121(2) . . ?
C20A C23A H23A 119.7 . . ?
C24A C23A H23A 119.7 . . ?
C23A C24A C25A 118(2) . . ?
C23A C24A C26A 120(2) . . ?
C25A C24A C26A 122(2) . . ?
C24A C25A C22A 121(2) . . ?
C24A C25A H25A 119.5 . . ?
C22A C25A H25A 119.5 . . ?
C21A C22A C25A 120(2) . . ?
C21A C22A H22A 120.1 . . ?
C25A C22A H22A 120.1 . . ?
C20A C21A C22A 119(2) . . ?
C20A C21A C19A 122(3) . . ?
C22A C21A C19A 119(3) . . ?
N1A C26A C24A 178(4) . . ?
C5A C6A C7A 125(3) . . ?
C5A C6A S1A 115(3) . . ?
C7A C6A S1A 120(3) . . ?
C6A C5A S2A 121(3) . . ?
C6A C5A H5A 119.7 . . ?
S2A C5A H5A 119.7 . . ?
C8A C7A C12A 118.1(19) . . ?
C8A C7A C6A 119(2) . . ?
C12A C7A C6A 122(2) . . ?
C7A C8A C9A 121(2) . . ?
C7A C8A H8A 119.4 . . ?
C9A C8A H8A 119.4 . . ?
C8A C9A C10A 120(2) . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A H9A 120.2 . . ?
C11A C10A C9A 121(2) . . ?
C11A C10A C13A 121(2) . . ?
C9A C10A C13A 119(2) . . ?
C10A C11A C12A 119(2) . . ?
C10A C11A H11A 120.6 . . ?
C12A C11A H11A 120.6 . . ?
C11A C12A C7A 122(2) . . ?
C11A C12A H12A 119.1 . . ?
C7A C12A H12A 119.1 . . ?
N2A C13A C10A 179(7) . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 986761'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cmpnd2
# start Validation Reply Form
_vrf_THETM01_cmpnd2              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The measured crystal diffracted weakly. Although the initial
measurement was performed to a theta range up to 52 deg/2Theta, 
reflections at 2Theta values greater than 46 deg were too weak (unobserved). 
Therefore the data set was cut-off for angles > 46 deg/2 theta.
Nevertheless, the refined structure has a data-to-parameter ratio of 9.7
(3658 independent reflections, 3157 observed (2 sigma threshold), 
325 parameters) and therefore we believe it is well determined.
;
_vrf_PLAT029_cmpnd2              
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.831 Note  
RESPONSE: see comment above.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H14 N2 S8'
_chemical_formula_sum            'C26 H14 N2 S8'
_chemical_formula_weight         610.88

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.119(2)
_cell_length_b                   8.3345(17)
_cell_length_c                   28.069(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.85(3)
_cell_angle_gamma                90.00
_cell_volume                     2587.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    32580
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       blocks
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_process_details   
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            9111
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         22.50
_reflns_number_total             2794
_reflns_number_gt                2352
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
; 
 HKL Denzo and Scalepack (Otwinowski & Minor 1997) 
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0141P)²+3.6881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2794
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
S1 S 0.03584(9) 0.62517(12) 0.22273(3) 0.0307(3) Uani 1 1 d . . .
S2 S 0.23501(9) 0.39201(12) 0.21479(3) 0.0313(3) Uani 1 1 d . . .
S3 S -0.15806(9) 0.32988(13) 0.22022(3) 0.0320(3) Uani 1 1 d . . .
S4 S 0.03434(10) 0.09683(12) 0.21224(3) 0.0339(3) Uani 1 1 d . . .
S5 S 0.07379(10) 0.76475(13) 0.11818(3) 0.0388(3) Uani 1 1 d . . .
S6 S 0.03604(11) 0.19273(13) 0.09783(3) 0.0406(3) Uani 1 1 d . . .
S7 S -0.15504(10) 0.43056(14) 0.10876(3) 0.0407(3) Uani 1 1 d . . .
S8 S 0.26622(10) 0.52529(14) 0.10864(3) 0.0414(3) Uani 1 1 d . . .
C4 C -0.0596(4) 0.2427(5) 0.18240(11) 0.0297(10) Uani 1 1 d . . .
C3 C -0.0599(4) 0.2839(5) 0.13603(12) 0.0303(10) Uani 1 1 d . . .
C19 C 0.0575(4) 0.5796(5) 0.31924(11) 0.0253(9) Uani 1 1 d . . .
C23 C 0.1395(3) 0.5389(5) 0.18721(11) 0.0273(9) Uani 1 1 d . . .
C22 C 0.1538(3) 0.3581(5) 0.26634(11) 0.0262(9) Uani 1 1 d . . .
H22 H 0.2102 0.3521 0.2955 0.031 Uiso 1 1 calc R . .
C24 C 0.1545(3) 0.5998(5) 0.14367(11) 0.0291(10) Uani 1 1 d . . .
C5 C -0.0449(3) 0.3373(4) 0.27189(11) 0.0249(9) Uani 1 1 d . . .
C6 C 0.0606(3) 0.2183(4) 0.26525(11) 0.0275(10) Uani 1 1 d . . .
H6 H 0.0769 0.1503 0.2937 0.033 Uiso 1 1 calc R . .
C21 C 0.0531(3) 0.4842(4) 0.27259(11) 0.0239(9) Uani 1 1 d . . .
C7 C -0.1097(4) 0.3227(5) 0.31721(11) 0.0269(9) Uani 1 1 d . . .
C25 C 0.1574(5) 0.7786(6) 0.06900(13) 0.0460(13) Uani 1 1 d . . .
H25 H 0.1414 0.8589 0.0462 0.055 Uiso 1 1 calc R . .
C8 C -0.2149(4) 0.4059(6) 0.32093(13) 0.0452(12) Uani 1 1 d . . .
H8 H -0.2513 0.4604 0.2944 0.054 Uiso 1 1 calc R . .
C11 C -0.2152(4) 0.3303(5) 0.40284(12) 0.0334(10) Uani 1 1 d . . .
C10 C -0.2679(4) 0.4101(5) 0.36330(13) 0.0438(12) Uani 1 1 d . . .
H10 H -0.3393 0.4670 0.3651 0.053 Uiso 1 1 calc R . .
C13 C -0.2670(4) 0.3433(6) 0.44804(14) 0.0428(11) Uani 1 1 d . . .
C15 C 0.0239(4) 0.7148(5) 0.40698(13) 0.0405(11) Uani 1 1 d . . .
C20 C 0.1298(4) 0.5346(5) 0.35972(12) 0.0430(12) Uani 1 1 d . . .
H20 H 0.1899 0.4580 0.3578 0.052 Uiso 1 1 calc R . .
C12 C -0.1130(4) 0.2416(6) 0.39926(13) 0.0504(13) Uani 1 1 d . . .
H12 H -0.0785 0.1837 0.4255 0.060 Uiso 1 1 calc R . .
C1 C -0.0932(5) 0.4216(6) 0.05411(13) 0.0487(13) Uani 1 1 d . . .
H1 H -0.1202 0.4897 0.0290 0.058 Uiso 1 1 calc R . .
N1 N -0.0318(5) 0.8169(7) 0.48905(14) 0.0909(17) Uani 1 1 d . . .
C18 C -0.0260(4) 0.7006(6) 0.32265(13) 0.0425(12) Uani 1 1 d . . .
H18 H -0.0711 0.7365 0.2950 0.051 Uiso 1 1 calc R . .
C2 C -0.0080(5) 0.3168(6) 0.04937(14) 0.0499(13) Uani 1 1 d . . .
H2 H 0.0281 0.3088 0.0210 0.060 Uiso 1 1 calc R . .
C17 C -0.0443(4) 0.7695(6) 0.36584(14) 0.0481(12) Uani 1 1 d . . .
H17 H -0.1009 0.8509 0.3675 0.058 Uiso 1 1 calc R . .
C26 C 0.2429(5) 0.6735(6) 0.06496(13) 0.0508(13) Uani 1 1 d . . .
H26 H 0.2901 0.6777 0.0395 0.061 Uiso 1 1 calc R . .
N2 N -0.3078(4) 0.3562(6) 0.48356(13) 0.0663(13) Uani 1 1 d . . .
C16 C 0.1124(5) 0.6042(6) 0.40356(13) 0.0528(14) Uani 1 1 d . . .
H16 H 0.1620 0.5746 0.4309 0.063 Uiso 1 1 calc R . .
C9 C -0.0611(4) 0.2381(6) 0.35662(13) 0.0463(12) Uani 1 1 d . . .
H9 H 0.0083 0.1772 0.3545 0.056 Uiso 1 1 calc R . .
C14 C -0.0052(5) 0.7741(7) 0.45307(16) 0.0624(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
S1 C23 1.753(4) . ?
S1 C21 1.822(3) . ?
S2 C23 1.749(4) . ?
S2 C22 1.805(3) . ?
S3 C4 1.757(4) . ?
S3 C5 1.821(3) . ?
S4 C4 1.759(4) . ?
S4 C6 1.799(3) . ?
S5 C25 1.745(4) . ?
S5 C24 1.754(4) . ?
S6 C2 1.739(5) . ?
S6 C3 1.761(4) . ?
S7 C3 1.741(4) . ?
S7 C1 1.746(4) . ?
S8 C26 1.741(5) . ?
S8 C24 1.773(4) . ?
C4 C3 1.346(5) . ?
C19 C20 1.375(5) . ?
C19 C18 1.381(6) . ?
C19 C21 1.528(5) . ?
C23 C24 1.349(5) . ?
C22 C6 1.557(5) . ?
C22 C21 1.558(5) . ?
C5 C7 1.529(5) . ?
C5 C6 1.563(5) . ?
C5 C21 1.638(5) . ?
C7 C8 1.373(6) . ?
C7 C9 1.375(5) . ?
C25 C26 1.306(6) . ?
C8 C10 1.381(5) . ?
C11 C12 1.368(6) . ?
C11 C10 1.373(5) . ?
C11 C13 1.450(5) . ?
C13 N2 1.141(5) . ?
C15 C16 1.359(6) . ?
C15 C17 1.392(6) . ?
C15 C14 1.452(6) . ?
C20 C16 1.391(5) . ?
C12 C9 1.381(5) . ?
C1 C2 1.305(6) . ?
N1 C14 1.138(5) . ?
C18 C17 1.375(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
C23 S1 C21 98.55(17) . . ?
C23 S2 C22 97.67(17) . . ?
C4 S3 C5 94.20(17) . . ?
C4 S4 C6 92.48(17) . . ?
C25 S5 C24 94.7(2) . . ?
C2 S6 C3 94.6(2) . . ?
C3 S7 C1 94.6(2) . . ?
C26 S8 C24 94.6(2) . . ?
C3 C4 S3 122.6(3) . . ?
C3 C4 S4 125.4(3) . . ?
S3 C4 S4 111.99(18) . . ?
C4 C3 S7 123.1(3) . . ?
C4 C3 S6 122.5(3) . . ?
S7 C3 S6 114.45(19) . . ?
C20 C19 C18 118.8(3) . . ?
C20 C19 C21 122.1(4) . . ?
C18 C19 C21 118.4(3) . . ?
C24 C23 S2 122.5(3) . . ?
C24 C23 S1 120.7(3) . . ?
S2 C23 S1 116.11(19) . . ?
C6 C22 C21 91.3(3) . . ?
C6 C22 S2 119.2(2) . . ?
C21 C22 S2 114.1(2) . . ?
C23 C24 S5 123.9(3) . . ?
C23 C24 S8 122.0(3) . . ?
S5 C24 S8 113.99(19) . . ?
C7 C5 C6 118.2(3) . . ?
C7 C5 C21 114.8(3) . . ?
C6 C5 C21 88.2(3) . . ?
C7 C5 S3 108.3(3) . . ?
C6 C5 S3 110.4(2) . . ?
C21 C5 S3 116.1(2) . . ?
C22 C6 C5 91.6(3) . . ?
C22 C6 S4 119.3(2) . . ?
C5 C6 S4 113.3(2) . . ?
C19 C21 C22 119.1(3) . . ?
C19 C21 C5 111.2(3) . . ?
C22 C21 C5 88.8(3) . . ?
C19 C21 S1 108.3(3) . . ?
C22 C21 S1 111.7(2) . . ?
C5 C21 S1 117.0(2) . . ?
C8 C7 C9 117.8(3) . . ?
C8 C7 C5 120.0(3) . . ?
C9 C7 C5 122.0(3) . . ?
C26 C25 S5 118.4(3) . . ?
C7 C8 C10 121.4(4) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 C13 120.8(4) . . ?
C10 C11 C13 119.7(4) . . ?
C11 C10 C8 120.0(4) . . ?
N2 C13 C11 178.9(5) . . ?
C16 C15 C17 120.0(3) . . ?
C16 C15 C14 121.5(4) . . ?
C17 C15 C14 118.4(4) . . ?
C19 C20 C16 119.7(4) . . ?
C11 C12 C9 119.9(4) . . ?
C2 C1 S7 118.3(3) . . ?
C17 C18 C19 121.8(4) . . ?
C1 C2 S6 117.9(3) . . ?
C18 C17 C15 118.5(4) . . ?
C25 C26 S8 118.2(3) . . ?
C15 C16 C20 120.8(4) . . ?
C7 C9 C12 121.5(4) . . ?
N1 C14 C15 177.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.831
_diffrn_reflns_theta_full        22.50
_diffrn_measured_fraction_theta_full 0.831
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 986762'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cmpnd3
# start Validation Reply Form
_vrf_PLAT019_cmpnd3              
;
PROBLEM: diffraction measured fraction theta full/max < 1.0  0.973

RESPONSE: The crystal was twinned (see below). Initially
a large number of disagreeable reflections were observed 
with Fo > Fc. After applying the twin law the agreement
was generally much better. However a small number of 
reflections (11) were omitted because of strong 
disagreement between Fo and Fc. Ten of the 11 were most
likely due to twinning (see below) and included both 
Fo > Fc and Fc > Fo. 1 low angle reflection
was not observed (obscured by beamstop).
;

_vrf_DIFMX01_cmpnd3              
;
PROBLEM: Maximum difference density is > 0.1*ZMAX*0.75
difference density max given = 1.516. Test value 1.200

RESPONSE: The crystal was twinned. Initial refinement stalled at
R1 ~ 0.18. Use of TwinRotMat in PLATON (SPEK) identified an
appropriate twin law (TWIN/BASF) which was subsequently applied
and afforded reduced residuals (R1 ~  0.08). However both the 
residual electron density (1.6e) and wR2 remained high.
Notably generation of an HKLF5 file led to a modest reduction in
residual electron density (1.12e-) compared to the initial
model but higher residuals (R1 ~ 0.10) and wR2.Both models gave
similar esd's on C-C bonds and the structure with the lower R1 was
selected.
;


# end Validation Reply Form


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H6 N2 S4'
_chemical_formula_sum            'C12 H6 N2 S4'
_chemical_formula_weight         306.43

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'
S S 0.1246 0.1234 '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                   3.9337(4)
_cell_length_b                   11.3951(9)
_cell_length_c                   27.644(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.393(5)
_cell_angle_gamma                90
_cell_volume                     1238.77(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3915
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.13

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.746
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
Bruker APEX-II, Bruker AXS, wisconsin, USA.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17919
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.004
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 1.004
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 1.004
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2213
_reflns_number_gt                1908
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component twin.
Initial structure solution in P2(1)/c revealed a single 
molecule in the asymmetric unit. Anisotropic refinement of all
non-H atoms proceeeded smoothly and H atoms added at calculated
positions. however refinement stalled at R1 ~17% with Fo > Fc
for many of the most disagreeable reflections. Examination of
the data with TwinrotMat in the PLATON suite (SPEK) revealed a
smal twin component which was refined with the suggested twin
law [-1 0 0 0 -1 0 0.342 0 1] and a BASF parameter 0.12.
This led to a halving of R1 (8.5%) but wR2 (25%) and the residual
electron density remained high 1.5e-. An alternative approach 
using HKLF5 afforded slightly lower residual electron density
(1.1e) but higher R1 (10.2%). The esd's on the bond lengths in 
both cases were comparable.  


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1541P)²+9.6439P] 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         2213
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0849
_refine_ls_wR_factor_ref         0.2704
_refine_ls_wR_factor_gt          0.2579
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_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 0.8726(6) 0.51388(19) 0.36460(8) 0.0247(6) Uani 1 1 d . . . . .
S2 S 0.5482(6) 0.73625(19) 0.39351(8) 0.0242(6) Uani 1 1 d . . . . .
S3 S 0.5265(6) 0.82194(18) 0.28220(8) 0.0228(6) Uani 1 1 d . . . . .
S4 S 0.8455(6) 0.59905(18) 0.25221(7) 0.0220(6) Uani 1 1 d . . . . .
N1 N 0.8784(19) 0.7402(6) 0.0736(3) 0.0236(16) Uani 1 1 d . . . . .
N2 N 1.276(2) 0.6209(8) -0.0226(3) 0.040(2) Uani 1 1 d . . . . .
C1 C 0.673(3) 0.6382(9) 0.4393(3) 0.032(2) Uani 1 1 d . . . . .
H1 H 0.6429 0.6563 0.4717 0.038 Uiso 1 1 calc R U . . .
C2 C 0.810(3) 0.5377(9) 0.4264(3) 0.032(2) Uani 1 1 d . . . . .
H2 H 0.8714 0.4814 0.4493 0.038 Uiso 1 1 calc R U . . .
C3 C 0.706(2) 0.6501(7) 0.3463(3) 0.0203(17) Uani 1 1 d . . . . .
C4 C 0.692(2) 0.6852(7) 0.2997(3) 0.0179(17) Uani 1 1 d . . . . .
C5 C 0.764(2) 0.7055(7) 0.2067(3) 0.0213(18) Uani 1 1 d . . . . .
C6 C 0.623(2) 0.8052(8) 0.2220(3) 0.0225(18) Uani 1 1 d . . . . .
H6 H 0.5769 0.8656 0.2001 0.027 Uiso 1 1 calc R U . . .
C7 C 0.861(2) 0.6779(7) 0.1573(3) 0.0202(17) Uani 1 1 d . . . . .
C8 C 1.032(2) 0.5755(8) 0.1454(3) 0.0230(18) Uani 1 1 d . . . . .
H8 H 1.0800 0.5196 0.1691 0.028 Uiso 1 1 calc R U . . .
C9 C 1.131(2) 0.5567(8) 0.0980(3) 0.0244(19) Uani 1 1 d . . . . .
H9 H 1.2467 0.4891 0.0893 0.029 Uiso 1 1 calc R U . . .
C10 C 1.051(2) 0.6422(8) 0.0647(3) 0.0237(18) Uani 1 1 d . . . . .
C11 C 0.783(2) 0.7551(8) 0.1191(3) 0.0257(19) Uani 1 1 d . . . . .
H11 H 0.6561 0.8216 0.1260 0.031 Uiso 1 1 calc R U . . .
C12 C 1.176(2) 0.6304(8) 0.0158(3) 0.030(2) 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
S1 C2 1.752(9) . ?
S1 C3 1.754(9) . ?
S2 C1 1.749(10) . ?
S2 C3 1.760(8) . ?
S3 C6 1.728(8) . ?
S3 C4 1.753(8) . ?
S4 C4 1.757(8) . ?
S4 C5 1.771(9) . ?
N1 C10 1.332(12) . ?
N1 C11 1.331(11) . ?
N2 C12 1.146(12) . ?
C1 C2 1.319(14) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.348(12) . ?
C5 C6 1.337(12) . ?
C5 C7 1.460(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(12) . ?
C7 C11 1.403(12) . ?
C8 C9 1.392(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(12) . ?
C9 H9 0.9300 . ?
C10 C12 1.457(12) . ?
C11 H11 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
C2 S1 C3 94.8(4) . . ?
C1 S2 C3 94.8(4) . . ?
C6 S3 C4 94.5(4) . . ?
C4 S4 C5 95.1(4) . . ?
C10 N1 C11 116.0(7) . . ?
C2 C1 S2 117.9(7) . . ?
C2 C1 H1 121.1 . . ?
S2 C1 H1 121.1 . . ?
C1 C2 S1 117.8(7) . . ?
C1 C2 H2 121.1 . . ?
S1 C2 H2 121.1 . . ?
C4 C3 S1 123.0(6) . . ?
C4 C3 S2 122.4(7) . . ?
S1 C3 S2 114.5(5) . . ?
C3 C4 S3 122.3(6) . . ?
C3 C4 S4 122.7(6) . . ?
S3 C4 S4 115.0(5) . . ?
C6 C5 C7 126.7(8) . . ?
C6 C5 S4 115.3(7) . . ?
C7 C5 S4 118.0(6) . . ?
C5 C6 S3 120.0(7) . . ?
C5 C6 H6 120.0 . . ?
S3 C6 H6 120.0 . . ?
C8 C7 C11 116.4(8) . . ?
C8 C7 C5 122.7(8) . . ?
C11 C7 C5 120.8(8) . . ?
C7 C8 C9 120.0(8) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 117.2(8) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
N1 C10 C9 125.4(8) . . ?
N1 C10 C12 115.8(8) . . ?
C9 C10 C12 118.7(8) . . ?
N1 C11 C7 124.8(8) . . ?
N1 C11 H11 117.6 . . ?
C7 C11 H11 117.6 . . ?
N2 C12 C10 179.5(11) . . ?

_refine_diff_density_max         1.516
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.190

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 986763'
