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

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#
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#                                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.
#
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#  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
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#  data retrieval see:
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data_mo_dm12215_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 N4 S4'
_chemical_formula_weight         546.77

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.2700(8)
_cell_length_b                   7.2800(11)
_cell_length_c                   18.461(3)
_cell_angle_alpha                92.723(2)
_cell_angle_beta                 96.980(3)
_cell_angle_gamma                110.788(3)
_cell_volume                     654.12(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    3293
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.63

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             286
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8922
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6423
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         30.64
_reflns_number_total             3961
_reflns_number_gt                3395
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0392P)²+0.1581P] 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         3961
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33795(5) 0.66208(4) 0.952524(14) 0.01295(7) Uani 1 1 d . . .
S2 S 1.07198(5) 1.05062(4) 0.890219(14) 0.01274(7) Uani 1 1 d . . .
N1 N -0.3500(2) 0.34582(16) 0.88649(6) 0.0205(2) Uani 1 1 d . . .
N2 N -0.0811(3) 0.4850(2) 0.67652(7) 0.0341(3) Uani 1 1 d . . .
C1 C -0.1740(2) 0.42925(17) 0.85537(6) 0.0156(2) Uani 1 1 d . . .
C2 C 0.0457(2) 0.53523(17) 0.81720(6) 0.0145(2) Uani 1 1 d . . .
C3 C -0.0179(3) 0.50914(18) 0.73891(7) 0.0199(2) Uani 1 1 d . . .
C4 C 0.2971(2) 0.65549(16) 0.85628(6) 0.0126(2) Uani 1 1 d . . .
C5 C 0.5382(2) 0.78258(16) 0.82930(6) 0.0126(2) Uani 1 1 d . . .
C6 C 0.7394(2) 0.87849(16) 0.88757(6) 0.0124(2) Uani 1 1 d . . .
C7 C 0.6701(2) 0.83287(16) 0.95911(6) 0.01222(19) Uani 1 1 d . . .
C8 C 0.8809(2) 0.93591(15) 1.01406(6) 0.0121(2) Uani 1 1 d . . .
C9 C 0.5627(2) 0.81883(17) 0.75045(6) 0.0149(2) Uani 1 1 d . . .
H9A H 0.4833 0.6911 0.7196 0.018 Uiso 1 1 calc R . .
H9B H 0.7592 0.8785 0.7451 0.018 Uiso 1 1 calc R . .
C10 C 0.4149(2) 0.95640(17) 0.72322(6) 0.0164(2) Uani 1 1 d . . .
H10A H 0.2181 0.8956 0.7281 0.020 Uiso 1 1 calc R . .
H10B H 0.4926 1.0830 0.7548 0.020 Uiso 1 1 calc R . .
C11 C 0.4402(3) 0.99772(18) 0.64377(6) 0.0177(2) Uani 1 1 d . . .
H11A H 0.3674 0.8711 0.6122 0.021 Uiso 1 1 calc R . .
H11B H 0.6365 1.0628 0.6390 0.021 Uiso 1 1 calc R . .
C12 C 0.2847(3) 1.12931(19) 0.61742(7) 0.0198(2) Uani 1 1 d . . .
H12A H 0.0859 1.0568 0.6166 0.024 Uiso 1 1 calc R . .
H12B H 0.3410 1.2479 0.6529 0.024 Uiso 1 1 calc R . .
C13 C 0.3333(3) 1.1949(2) 0.54140(7) 0.0217(2) Uani 1 1 d . . .
H13A H 0.5326 1.2636 0.5415 0.026 Uiso 1 1 calc R . .
H13B H 0.2703 1.0769 0.5054 0.026 Uiso 1 1 calc R . .
C14 C 0.1843(3) 1.3321(2) 0.51741(8) 0.0290(3) Uani 1 1 d . . .
H14A H -0.0131 1.2653 0.5175 0.043 Uiso 1 1 calc R . .
H14B H 0.2177 1.3668 0.4679 0.043 Uiso 1 1 calc R . .
H14C H 0.2526 1.4524 0.5514 0.043 Uiso 1 1 calc R . .

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
S1 0.01063(13) 0.01404(13) 0.01193(12) 0.00195(9) 0.00111(9) 0.00184(10)
S2 0.01067(13) 0.01406(13) 0.01149(12) 0.00185(9) 0.00104(9) 0.00221(10)
N1 0.0160(5) 0.0206(5) 0.0204(5) -0.0014(4) 0.0009(4) 0.0021(4)
N2 0.0289(7) 0.0381(7) 0.0205(5) -0.0008(5) -0.0010(5) -0.0037(5)
C1 0.0140(5) 0.0144(5) 0.0155(5) -0.0018(4) -0.0016(4) 0.0034(4)
C2 0.0123(5) 0.0143(5) 0.0146(5) -0.0001(4) 0.0000(4) 0.0029(4)
C3 0.0154(6) 0.0199(6) 0.0185(5) -0.0002(4) 0.0006(4) 0.0002(4)
C4 0.0120(5) 0.0129(5) 0.0126(4) 0.0008(4) 0.0006(4) 0.0047(4)
C5 0.0120(5) 0.0129(5) 0.0123(4) 0.0010(4) 0.0007(4) 0.0041(4)
C6 0.0115(5) 0.0120(5) 0.0135(4) 0.0020(4) 0.0022(4) 0.0038(4)
C7 0.0106(5) 0.0120(5) 0.0127(4) 0.0012(4) 0.0003(4) 0.0030(4)
C8 0.0116(5) 0.0122(5) 0.0121(4) 0.0016(4) 0.0012(4) 0.0040(4)
C9 0.0131(5) 0.0190(5) 0.0121(4) 0.0018(4) 0.0024(4) 0.0048(4)
C10 0.0183(6) 0.0175(5) 0.0139(5) 0.0026(4) 0.0028(4) 0.0067(4)
C11 0.0185(6) 0.0216(6) 0.0142(5) 0.0049(4) 0.0037(4) 0.0078(5)
C12 0.0184(6) 0.0233(6) 0.0190(5) 0.0069(4) 0.0041(4) 0.0084(5)
C13 0.0201(6) 0.0243(6) 0.0215(6) 0.0100(5) 0.0039(5) 0.0077(5)
C14 0.0254(7) 0.0297(7) 0.0338(7) 0.0157(6) 0.0036(6) 0.0111(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
S1 C7 1.7362(12) . ?
S1 C4 1.7599(11) . ?
S2 C8 1.7474(11) 2_777 ?
S2 C6 1.7489(12) . ?
N1 C1 1.1495(16) . ?
N2 C3 1.1465(17) . ?
C1 C2 1.4314(16) . ?
C2 C4 1.3878(15) . ?
C2 C3 1.4312(16) . ?
C4 C5 1.4427(15) . ?
C5 C6 1.3767(15) . ?
C5 C9 1.5046(15) . ?
C6 C7 1.4356(15) . ?
C7 C8 1.3741(15) . ?
C8 C8 1.445(2) 2_777 ?
C8 S2 1.7474(11) 2_777 ?
C9 C10 1.5390(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5235(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5267(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5255(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5244(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C7 S1 C4 90.78(5) . . ?
C8 S2 C6 89.81(5) 2_777 . ?
N1 C1 C2 179.31(13) . . ?
C4 C2 C3 124.71(11) . . ?
C4 C2 C1 120.00(10) . . ?
C3 C2 C1 115.28(10) . . ?
N2 C3 C2 176.92(14) . . ?
C2 C4 C5 129.06(10) . . ?
C2 C4 S1 117.80(8) . . ?
C5 C4 S1 113.13(8) . . ?
C6 C5 C4 109.48(10) . . ?
C6 C5 C9 124.40(10) . . ?
C4 C5 C9 125.97(10) . . ?
C5 C6 C7 116.04(10) . . ?
C5 C6 S2 131.00(9) . . ?
C7 C6 S2 112.96(8) . . ?
C8 C7 C6 112.31(10) . . ?
C8 C7 S1 137.11(9) . . ?
C6 C7 S1 110.57(8) . . ?
C7 C8 C8 112.33(12) . 2_777 ?
C7 C8 S2 135.08(9) . 2_777 ?
C8 C8 S2 112.59(10) 2_777 2_777 ?
C5 C9 C10 112.01(9) . . ?
C5 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C5 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 113.01(9) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 111.96(10) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 113.61(10) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 112.68(11) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N1 C1 C2 C4 45(12) . . . . ?
N1 C1 C2 C3 -134(12) . . . . ?
C4 C2 C3 N2 -162(3) . . . . ?
C1 C2 C3 N2 17(3) . . . . ?
C3 C2 C4 C5 2.7(2) . . . . ?
C1 C2 C4 C5 -176.11(11) . . . . ?
C3 C2 C4 S1 -178.16(10) . . . . ?
C1 C2 C4 S1 3.04(15) . . . . ?
C7 S1 C4 C2 -178.79(10) . . . . ?
C7 S1 C4 C5 0.49(9) . . . . ?
C2 C4 C5 C6 178.64(11) . . . . ?
S1 C4 C5 C6 -0.54(12) . . . . ?
C2 C4 C5 C9 3.04(19) . . . . ?
S1 C4 C5 C9 -176.15(9) . . . . ?
C4 C5 C6 C7 0.32(14) . . . . ?
C9 C5 C6 C7 176.01(10) . . . . ?
C4 C5 C6 S2 -179.45(9) . . . . ?
C9 C5 C6 S2 -3.76(18) . . . . ?
C8 S2 C6 C5 179.33(12) 2_777 . . . ?
C8 S2 C6 C7 -0.44(9) 2_777 . . . ?
C5 C6 C7 C8 -179.46(10) . . . . ?
S2 C6 C7 C8 0.35(12) . . . . ?
C5 C6 C7 S1 0.04(13) . . . . ?
S2 C6 C7 S1 179.85(6) . . . . ?
C4 S1 C7 C8 179.03(13) . . . . ?
C4 S1 C7 C6 -0.30(8) . . . . ?
C6 C7 C8 C8 -0.02(16) . . . 2_777 ?
S1 C7 C8 C8 -179.34(10) . . . 2_777 ?
C6 C7 C8 S2 179.57(9) . . . 2_777 ?
S1 C7 C8 S2 0.2(2) . . . 2_777 ?
C6 C5 C9 C10 -99.62(13) . . . . ?
C4 C5 C9 C10 75.36(14) . . . . ?
C5 C9 C10 C11 179.19(10) . . . . ?
C9 C10 C11 C12 178.27(10) . . . . ?
C10 C11 C12 C13 172.93(11) . . . . ?
C11 C12 C13 C14 -177.92(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        30.64
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 945698'
