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

#######################################################################
#
#                 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_2a
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 N2 S5'
_chemical_formula_sum            'C14 H6 N2 S5'
_chemical_formula_weight         362.51

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   P

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                   15.3554(6)
_cell_length_b                   5.1394(3)
_cell_length_c                   19.8167(11)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 110.249(3)
_cell_angle_gamma                90.000(4)
_cell_volume                     1467.23(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3327
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.0

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_T_max  0.7456
_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  'Nonius Kappa CCD'
_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            20406
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3197
_reflns_number_gt                2124
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       KappaCCD
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'Denzo and Scalepak'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0282P)²+1.0110P] 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         3197
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6877(2) 1.0845(6) 0.13656(15) 0.0413(7) Uani 1 1 d . . .
H1 H 0.7278 1.2258 0.1446 0.050 Uiso 1 1 calc R . .
C2 C 0.64499(19) 0.9944(6) 0.07054(15) 0.0413(7) Uani 1 1 d . . .
H2 H 0.6537 1.0713 0.0309 0.050 Uiso 1 1 calc R . .
C3 C 0.58576(18) 0.7081(5) 0.15250(13) 0.0285(6) Uani 1 1 d . . .
C4 C 0.53745(17) 0.5393(5) 0.17685(13) 0.0273(6) Uani 1 1 d . . .
C5 C 0.46958(18) 0.2600(5) 0.25510(14) 0.0334(6) Uani 1 1 d . . .
H5 H 0.4572 0.1874 0.2938 0.040 Uiso 1 1 calc R . .
C6 C 0.42552(17) 0.1737(5) 0.18803(13) 0.0292(6) Uani 1 1 d . . .
C7 C 0.35786(19) -0.0258(5) 0.16639(14) 0.0334(6) Uani 1 1 d . . .
C8 C 0.30033(19) -0.1924(6) 0.14447(14) 0.0356(7) Uani 1 1 d . . .
C9 C 0.23081(18) -0.3910(5) 0.12213(15) 0.0331(6) Uani 1 1 d . . .
C10 C 0.19740(19) -0.5142(6) 0.16901(16) 0.0395(7) Uani 1 1 d . . .
H10 H 0.2209 -0.4679 0.2173 0.047 Uiso 1 1 calc R . .
C11 C 0.1281(2) -0.7104(6) 0.14701(17) 0.0458(8) Uani 1 1 d . . .
H11 H 0.1077 -0.7877 0.1813 0.055 Uiso 1 1 calc R . .
C12 C 0.0910(2) -0.7882(6) 0.07774(17) 0.0478(8) Uani 1 1 d . . .
H12 H 0.0454 -0.9163 0.0641 0.057 Uiso 1 1 calc R . .
C13 C 0.12340(19) -0.6691(6) 0.02665(16) 0.0419(7) Uani 1 1 d . . .
C14 C 0.19274(18) -0.4707(5) 0.04803(15) 0.0357(7) Uani 1 1 d . . .
N1 N 0.21712(18) -0.3758(5) -0.00613(14) 0.0531(7) Uani 1 1 d . . .
N2 N 0.09601(19) -0.7233(6) -0.04457(14) 0.0598(8) Uani 1 1 d . . .
S1 S 0.66659(5) 0.93068(14) 0.20762(4) 0.03580(19) Uani 1 1 d . . .
S2 S 0.57237(6) 0.72856(15) 0.06097(4) 0.0438(2) Uani 1 1 d . . .
S3 S 0.54984(5) 0.50859(14) 0.26853(3) 0.03496(19) Uani 1 1 d . . .
S4 S 0.45488(5) 0.32634(14) 0.11923(4) 0.0365(2) Uani 1 1 d . . .
S5 S 0.15562(7) -0.5341(2) -0.07715(5) 0.0744(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0375(17) 0.0389(17) 0.0446(17) 0.0056(14) 0.0105(14) -0.0131(14)
C2 0.0437(17) 0.0431(18) 0.0375(16) 0.0062(14) 0.0144(14) -0.0111(15)
C3 0.0304(15) 0.0252(14) 0.0274(13) -0.0010(11) 0.0066(11) -0.0002(12)
C4 0.0303(14) 0.0251(14) 0.0248(13) -0.0036(11) 0.0074(11) -0.0024(12)
C5 0.0379(16) 0.0352(16) 0.0314(14) 0.0015(13) 0.0174(12) -0.0038(13)
C6 0.0261(14) 0.0289(15) 0.0341(15) -0.0017(12) 0.0122(12) -0.0020(12)
C7 0.0333(15) 0.0338(16) 0.0351(15) -0.0004(13) 0.0144(12) -0.0009(14)
C8 0.0360(16) 0.0347(16) 0.0373(16) -0.0033(13) 0.0143(13) -0.0032(15)
C9 0.0291(15) 0.0299(15) 0.0417(16) -0.0021(13) 0.0138(13) -0.0025(13)
C10 0.0400(17) 0.0416(17) 0.0420(16) -0.0037(14) 0.0207(14) -0.0038(15)
C11 0.0457(19) 0.0424(18) 0.058(2) 0.0022(16) 0.0290(16) -0.0095(16)
C12 0.0374(17) 0.0430(19) 0.064(2) -0.0070(16) 0.0182(16) -0.0179(15)
C13 0.0332(17) 0.0415(18) 0.0467(18) -0.0048(15) 0.0084(13) -0.0096(14)
C14 0.0307(15) 0.0337(16) 0.0428(16) 0.0044(14) 0.0127(13) -0.0030(13)
N1 0.0556(17) 0.0604(18) 0.0427(14) 0.0015(14) 0.0162(13) -0.0204(15)
N2 0.0564(18) 0.068(2) 0.0459(16) -0.0084(15) 0.0068(13) -0.0231(16)
S1 0.0371(4) 0.0341(4) 0.0301(4) 0.0001(3) 0.0038(3) -0.0090(3)
S2 0.0616(5) 0.0409(4) 0.0279(4) -0.0033(3) 0.0142(3) -0.0189(4)
S3 0.0400(4) 0.0372(4) 0.0267(3) -0.0052(3) 0.0103(3) -0.0095(3)
S4 0.0441(4) 0.0372(4) 0.0272(3) -0.0057(3) 0.0112(3) -0.0145(3)
S5 0.0811(7) 0.0975(8) 0.0399(5) -0.0052(5) 0.0149(5) -0.0378(6)

_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
C1 C2 1.327(4) . ?
C1 S1 1.741(3) . ?
C1 H1 0.9300 . ?
C2 S2 1.732(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.335(3) . ?
C3 S2 1.757(3) . ?
C3 S1 1.762(3) . ?
C4 S4 1.763(2) . ?
C4 S3 1.767(2) . ?
C5 C6 1.341(3) . ?
C5 S3 1.731(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(4) . ?
C6 S4 1.762(3) . ?
C7 C8 1.199(4) . ?
C8 C9 1.432(4) . ?
C9 C10 1.363(4) . ?
C9 C14 1.439(4) . ?
C10 C11 1.420(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.352(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.413(4) . ?
C12 H12 0.9300 . ?
C13 N2 1.355(4) . ?
C13 C14 1.428(4) . ?
C14 N1 1.345(3) . ?
N1 S5 1.617(3) . ?
N2 S5 1.615(3) . ?

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 C1 S1 118.2(2) . . ?
C2 C1 H1 120.9 . . ?
S1 C1 H1 120.9 . . ?
C1 C2 S2 117.6(2) . . ?
C1 C2 H2 121.2 . . ?
S2 C2 H2 121.2 . . ?
C4 C3 S2 122.07(19) . . ?
C4 C3 S1 123.92(19) . . ?
S2 C3 S1 114.01(15) . . ?
C3 C4 S4 122.29(19) . . ?
C3 C4 S3 123.63(19) . . ?
S4 C4 S3 114.07(14) . . ?
C6 C5 S3 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
S3 C5 H5 120.5 . . ?
C5 C6 C7 127.2(2) . . ?
C5 C6 S4 116.3(2) . . ?
C7 C6 S4 116.45(19) . . ?
C8 C7 C6 176.6(3) . . ?
C7 C8 C9 176.7(3) . . ?
C10 C9 C8 122.5(3) . . ?
C10 C9 C14 116.6(2) . . ?
C8 C9 C14 121.0(2) . . ?
C9 C10 C11 122.6(3) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
N2 C13 C12 126.7(3) . . ?
N2 C13 C14 112.7(3) . . ?
C12 C13 C14 120.5(3) . . ?
N1 C14 C13 114.0(3) . . ?
N1 C14 C9 125.7(3) . . ?
C13 C14 C9 120.2(3) . . ?
C14 N1 S5 105.8(2) . . ?
C13 N2 S5 106.1(2) . . ?
C1 S1 C3 94.69(13) . . ?
C2 S2 C3 95.36(13) . . ?
C5 S3 C4 95.18(12) . . ?
C6 S4 C4 95.43(12) . . ?
N2 S5 N1 101.31(14) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 1027242'
