# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_sad

_audit_creation_date             2014-02-14T14:57:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C29 H18 N4 S4, C H Cl3'
_chemical_formula_sum            'C30 H19 Cl3 N4 S4'
_chemical_formula_weight         670.08

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7895(8)
_cell_length_b                   11.882(3)
_cell_length_c                   17.8299(6)
_cell_angle_alpha                84.474(9)
_cell_angle_beta                 78.079(4)
_cell_angle_gamma                80.66(2)
_cell_volume                     1589.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7703
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      27.56

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.4
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            37540
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_full        27
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.99
_reflns_number_total             7241
_reflns_number_gt                3982
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2i (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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.
The restraint corresponds to a SUMP instruction between Cl1, Cl2 and Cl4. Cl3 site occupancy has been refined to 1.02 and then fixed to 1.

;
_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)+(0.0745P)²+2.2189P] 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_number_reflns         7241
_refine_ls_number_parameters     378
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1666
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1961
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.57

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 1.0973(6) 0.6137(4) 0.8431(2) 0.0499(11) Uani 1 d . . .
C2 C 1.0358(6) 0.7276(4) 0.8565(3) 0.0554(12) Uani 1 d . . .
H2 H 1.034 0.7583 0.9028 0.066 Uiso 1 calc R . .
C3 C 0.9772(6) 0.7919(4) 0.7950(3) 0.0543(11) Uani 1 d . . .
H3 H 0.9326 0.8694 0.796 0.065 Uiso 1 calc R . .
C4 C 0.9919(5) 0.7291(3) 0.7323(2) 0.0435(10) Uani 1 d . . .
C5 C 0.9475(5) 0.7635(3) 0.6581(2) 0.0445(10) Uani 1 d . . .
C6 C 0.9680(7) 0.6966(4) 0.5970(3) 0.0594(12) Uani 1 d . . .
H6 H 1.0152 0.6195 0.5981 0.071 Uiso 1 calc R . .
C7 C 0.9109(6) 0.7564(4) 0.5336(3) 0.0549(12) Uani 1 d . . .
C8 C 0.8457(5) 0.8701(3) 0.5454(2) 0.0434(10) Uani 1 d . . .
C9 C 0.7879(5) 0.9240(3) 0.4771(2) 0.0433(10) Uani 1 d . . .
C10 C 0.8160(7) 0.8431(3) 0.4230(3) 0.0562(12) Uani 1 d . . .
C11 C 0.8991(8) 0.7271(4) 0.4528(3) 0.0655(14) Uani 1 d . . .
C12 C 0.7634(7) 0.8868(4) 0.3545(3) 0.0599(13) Uani 1 d . . .
H12 H 0.7737 0.8437 0.3125 0.072 Uiso 1 calc R . .
C13 C 0.6942(5) 1.0014(3) 0.3561(2) 0.0460(10) Uani 1 d . . .
C14 C 0.6283(5) 1.0698(3) 0.2932(3) 0.0439(10) Uani 1 d . . .
C15 C 0.6122(8) 1.0281(4) 0.2257(3) 0.0697(15) Uani 1 d . . .
H15 H 0.6413 0.9515 0.215 0.084 Uiso 1 calc R . .
C16 C 0.5475(8) 1.1137(4) 0.1756(3) 0.0717(15) Uani 1 d . . .
H16 H 0.5324 1.0998 0.1271 0.086 Uiso 1 calc R . .
C17 C 0.5075(6) 1.2209(4) 0.2035(3) 0.0509(11) Uani 1 d . . .
C18 C 1.1631(6) 0.5295(4) 0.8961(3) 0.0563(12) Uani 1 d . . .
H18 H 1.165 0.5551 0.9436 0.068 Uiso 1 calc R . .
C19 C 1.2237(7) 0.4168(4) 0.8875(3) 0.0591(12) Uani 1 d . . .
C20 C 1.2860(8) 0.3413(5) 0.9485(3) 0.0706(14) Uani 1 d . . .
C21 C 1.2314(9) 0.3606(5) 0.8198(3) 0.0760(16) Uani 1 d . . .
C22 C 0.4370(6) 1.3187(4) 0.1610(3) 0.0580(12) Uani 1 d . . .
H22 H 0.4218 1.304 0.1127 0.07 Uiso 1 calc R . .
C23 C 0.3879(6) 1.4293(4) 0.1779(3) 0.0580(12) Uani 1 d . . .
C24 C 0.3202(7) 1.5123(5) 0.1234(4) 0.0742(16) Uani 1 d . . .
C25 C 0.3994(7) 1.4678(4) 0.2493(4) 0.0711(15) Uani 1 d . . .
C26 C 0.7798(10) 0.6342(4) 0.4552(4) 0.089(2) Uani 1 d . . .
H26A H 0.7738 0.6222 0.4028 0.106 Uiso 1 calc R . .
H26B H 0.8366 0.5633 0.4768 0.106 Uiso 1 calc R . .
C27 C 0.5941(10) 0.6589(5) 0.5001(5) 0.105(2) Uani 1 d . . .
H27A H 0.5972 0.6633 0.5533 0.157 Uiso 1 calc R . .
H27B H 0.5292 0.5988 0.495 0.157 Uiso 1 calc R . .
H27C H 0.5371 0.7303 0.4807 0.157 Uiso 1 calc R . .
C28 C 1.0843(9) 0.6879(4) 0.4043(3) 0.0805(19) Uani 1 d . . .
H28A H 1.135 0.6173 0.4285 0.097 Uiso 1 calc R . .
H28B H 1.0688 0.6708 0.3542 0.097 Uiso 1 calc R . .
C29 C 1.2145(9) 0.7701(6) 0.3927(4) 0.093(2) Uani 1 d . . .
H29A H 1.1701 0.8388 0.3655 0.14 Uiso 1 calc R . .
H29B H 1.3255 0.7364 0.3635 0.14 Uiso 1 calc R . .
H29C H 1.2317 0.7881 0.4418 0.14 Uiso 1 calc R . .
C30 C 0.2124(10) 0.8569(6) 0.0933(4) 0.104(2) Uani 1 d . . .
H30 H 0.2918 0.7928 0.0683 0.125 Uiso 1 calc R 1 A
N1 N 1.2406(11) 0.3130(5) 0.7674(3) 0.124(2) Uani 1 d . . .
N2 N 1.3349(8) 0.2793(5) 0.9946(3) 0.1005(17) Uani 1 d . . .
N3 N 0.2665(8) 1.5761(4) 0.0788(4) 0.1064(19) Uani 1 d . . .
N4 N 0.4112(9) 1.4982(5) 0.3070(4) 0.107(2) Uani 1 d . . .
S1 S 1.08098(15) 0.58862(9) 0.75031(6) 0.0479(3) Uani 1 d . . .
S2 S 0.85362(13) 0.90400(8) 0.63591(6) 0.0422(3) Uani 1 d . . .
S3 S 0.69501(13) 1.05546(8) 0.44344(6) 0.0399(3) Uani 1 d . . .
S4 S 0.55817(13) 1.21499(8) 0.29417(6) 0.0434(3) Uani 1 d . . .
Cl1 Cl 0.2922(4) 0.9831(2) 0.04997(15) 0.1415(13) Uani 0.907(6) d P . B
Cl2 Cl 0.0029(4) 0.8587(3) 0.0691(2) 0.1572(16) Uani 0.829(6) d P 1 B
Cl3 Cl 0.2272(8) 0.8418(4) 0.18635(18) 0.268(2) Uani 1 d . . B
Cl4 Cl -0.0106(15) 0.9103(10) 0.1318(8) 0.1572(16) Uani 0.262(5) d P 2 B



#------------------ 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
C1 C2 1.387(6) . ?
C1 C18 1.417(6) . ?
C1 S1 1.742(4) . ?
C2 C3 1.388(6) . ?
C2 H2 0.93 . ?
C3 C4 1.379(6) . ?
C3 H3 0.93 . ?
C4 C5 1.440(6) . ?
C4 S1 1.728(4) . ?
C5 C6 1.378(6) . ?
C5 S2 1.753(4) . ?
C6 C7 1.389(6) . ?
C6 H6 0.93 . ?
C7 C8 1.384(5) . ?
C7 C11 1.538(6) . ?
C8 C9 1.443(6) . ?
C8 S2 1.715(4) . ?
C9 C10 1.387(6) . ?
C9 S3 1.719(4) . ?
C10 C12 1.395(6) . ?
C10 C11 1.521(6) . ?
C11 C26 1.546(8) . ?
C11 C28 1.546(8) . ?
C12 C13 1.381(6) . ?
C12 H12 0.93 . ?
C13 C14 1.452(6) . ?
C13 S3 1.742(4) . ?
C14 C15 1.381(6) . ?
C14 S4 1.724(4) . ?
C15 C16 1.390(7) . ?
C15 H15 0.93 . ?
C16 C17 1.377(6) . ?
C16 H16 0.93 . ?
C17 C22 1.421(6) . ?
C17 S4 1.734(5) . ?
C18 C19 1.358(7) . ?
C18 H18 0.93 . ?
C19 C21 1.421(8) . ?
C19 C20 1.453(7) . ?
C20 N2 1.134(6) . ?
C21 N1 1.121(7) . ?
C22 C23 1.352(7) . ?
C22 H22 0.93 . ?
C23 C25 1.417(8) . ?
C23 C24 1.432(7) . ?
C24 N3 1.140(6) . ?
C25 N4 1.150(8) . ?
C26 C27 1.499(9) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C27 H27A 0.96 . ?
C27 H27B 0.96 . ?
C27 H27C 0.96 . ?
C28 C29 1.490(9) . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C29 H29A 0.96 . ?
C29 H29B 0.96 . ?
C29 H29C 0.96 . ?
C30 Cl3 1.676(8) . ?
C30 Cl1 1.764(8) . ?
C30 Cl4 1.768(14) . ?
C30 Cl2 1.768(8) . ?
C30 H30 0.98 . ?

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 C18 125.8(4) . . ?
C2 C1 S1 109.5(3) . . ?
C18 C1 S1 124.7(4) . . ?
C1 C2 C3 114.3(4) . . ?
C1 C2 H2 122.9 . . ?
C3 C2 H2 122.9 . . ?
C4 C3 C2 113.1(4) . . ?
C4 C3 H3 123.5 . . ?
C2 C3 H3 123.5 . . ?
C3 C4 C5 130.3(4) . . ?
C3 C4 S1 111.0(3) . . ?
C5 C4 S1 118.7(3) . . ?
C6 C5 C4 127.5(4) . . ?
C6 C5 S2 111.0(3) . . ?
C4 C5 S2 121.4(3) . . ?
C5 C6 C7 113.0(4) . . ?
C5 C6 H6 123.5 . . ?
C7 C6 H6 123.5 . . ?
C8 C7 C6 113.2(4) . . ?
C8 C7 C11 111.1(4) . . ?
C6 C7 C11 135.7(4) . . ?
C7 C8 C9 109.0(4) . . ?
C7 C8 S2 111.9(3) . . ?
C9 C8 S2 139.1(3) . . ?
C10 C9 C8 108.7(3) . . ?
C10 C9 S3 111.8(3) . . ?
C8 C9 S3 139.5(3) . . ?
C9 C10 C12 113.2(4) . . ?
C9 C10 C11 111.7(4) . . ?
C12 C10 C11 135.1(4) . . ?
C10 C11 C7 99.6(3) . . ?
C10 C11 C26 111.9(4) . . ?
C7 C11 C26 112.4(5) . . ?
C10 C11 C28 111.9(4) . . ?
C7 C11 C28 111.8(4) . . ?
C26 C11 C28 109.1(4) . . ?
C13 C12 C10 112.4(4) . . ?
C13 C12 H12 123.8 . . ?
C10 C12 H12 123.8 . . ?
C12 C13 C14 124.8(4) . . ?
C12 C13 S3 111.8(3) . . ?
C14 C13 S3 123.4(3) . . ?
C15 C14 C13 125.1(4) . . ?
C15 C14 S4 111.3(3) . . ?
C13 C14 S4 123.7(3) . . ?
C14 C15 C16 112.3(4) . . ?
C14 C15 H15 123.9 . . ?
C16 C15 H15 123.9 . . ?
C17 C16 C15 114.6(5) . . ?
C17 C16 H16 122.7 . . ?
C15 C16 H16 122.7 . . ?
C16 C17 C22 122.7(4) . . ?
C16 C17 S4 109.8(3) . . ?
C22 C17 S4 127.5(4) . . ?
C19 C18 C1 129.2(4) . . ?
C19 C18 H18 115.4 . . ?
C1 C18 H18 115.4 . . ?
C18 C19 C21 124.4(4) . . ?
C18 C19 C20 122.2(5) . . ?
C21 C19 C20 113.4(5) . . ?
N2 C20 C19 177.6(6) . . ?
N1 C21 C19 177.6(6) . . ?
C23 C22 C17 131.9(5) . . ?
C23 C22 H22 114 . . ?
C17 C22 H22 114 . . ?
C22 C23 C25 122.2(4) . . ?
C22 C23 C24 120.4(5) . . ?
C25 C23 C24 117.4(5) . . ?
N3 C24 C23 178.2(7) . . ?
N4 C25 C23 179.0(6) . . ?
C27 C26 C11 116.1(4) . . ?
C27 C26 H26A 108.3 . . ?
C11 C26 H26A 108.3 . . ?
C27 C26 H26B 108.3 . . ?
C11 C26 H26B 108.3 . . ?
H26A C26 H26B 107.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C11 116.4(4) . . ?
C29 C28 H28A 108.2 . . ?
C11 C28 H28A 108.2 . . ?
C29 C28 H28B 108.2 . . ?
C11 C28 H28B 108.2 . . ?
H28A C28 H28B 107.4 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl3 C30 Cl1 110.2(4) . . ?
Cl3 C30 Cl4 82.3(6) . . ?
Cl1 C30 Cl4 101.1(5) . . ?
Cl3 C30 Cl2 118.6(5) . . ?
Cl1 C30 Cl2 106.8(4) . . ?
Cl4 C30 Cl2 43.2(5) . . ?
Cl3 C30 H30 106.9 . . ?
Cl1 C30 H30 106.9 . . ?
Cl4 C30 H30 144.8 . . ?
Cl2 C30 H30 106.9 . . ?
C4 S1 C1 92.1(2) . . ?
C8 S2 C5 90.9(2) . . ?
C9 S3 C13 90.9(2) . . ?
C14 S4 C17 92.0(2) . . ?

_database_code_depnum_ccdc_archive 'CCDC 1007813'
