# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2012


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#                                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. 
# 
#  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 
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#  data retrieval see:
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data_TTFesterdimer
_database_code_depnum_ccdc_archive 'CCDC 876433'
#TrackingRef 'cif_esterdimer.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            TTFesterdimer
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 O4 S8, C2 O'
_chemical_formula_sum            'C26 H16 O5 S8'
_chemical_formula_weight         664.87

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'
O O 0.0106 0.0060 '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                   6.0600(6)
_cell_length_b                   12.2550(7)
_cell_length_c                   19.5350(9)
_cell_angle_alpha                79.509(4)
_cell_angle_beta                 81.926(6)
_cell_angle_gamma                76.549(5)
_cell_volume                     1380.07(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9389
_cell_measurement_theta_min      1.73
_cell_measurement_theta_max      26.52

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02

_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.685

_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)



_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_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            9389
_diffrn_reflns_av_R_equivalents  0.1835
_diffrn_reflns_av_sigmaI/netI    0.4231
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.52
_reflns_number_total             5549
_reflns_number_gt                1676
_reflns_threshold_expression     >2\s(I)


_computing_data_collection       'BRUKER APEX2 (Bruker, 2005)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.165(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5549
_refine_ls_number_parameters     350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3373
_refine_ls_R_factor_gt           0.1673
_refine_ls_wR_factor_ref         0.4702
_refine_ls_wR_factor_gt          0.4192
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.661
_refine_ls_shift/su_mean         0.040

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 0.6084(9) 0.1958(4) 0.2898(3) 0.0422(14) Uani 1 1 d . . .
S2 S 0.2103(9) 0.2075(4) 0.2131(3) 0.0409(14) Uani 1 1 d . . .
S3 S -0.0678(8) 0.4173(4) 0.2883(3) 0.0391(14) Uani 1 1 d . . .
S4 S 0.3323(9) 0.4195(4) 0.3578(3) 0.0385(14) Uani 1 1 d . . .
S5 S 0.6676(8) 0.4157(4) 0.1273(2) 0.0392(14) Uani 1 1 d . . .
S6 S 0.2418(9) 0.4491(4) 0.0612(3) 0.0401(14) Uani 1 1 d . . .
S7 S 0.0045(8) 0.6418(4) 0.1629(3) 0.0391(14) Uani 1 1 d . . .
S8 S 0.4395(9) 0.6104(4) 0.2207(3) 0.0403(14) Uani 1 1 d . . .
O1 O 0.054(2) 0.8239(10) 0.3320(7) 0.042(4) Uani 1 1 d . . .
O2 O 0.428(2) 0.7644(11) 0.3123(6) 0.039(3) Uani 1 1 d . . .
O3 O -0.102(3) 0.6166(13) 0.4499(8) 0.057(4) Uani 1 1 d . . .
O4 O 0.285(2) 0.6021(11) 0.4387(6) 0.039(3) Uani 1 1 d . . .
C1 C 0.222(3) 0.3642(16) 0.2956(8) 0.033(5) Uani 1 1 d . . .
C2 C 0.335(3) 0.2696(18) 0.2710(9) 0.038(5) Uani 1 1 d . . .
C3 C 0.646(4) 0.1057(16) 0.2285(9) 0.041(5) Uani 1 1 d . . .
C4 C 0.842(4) 0.0239(17) 0.2157(14) 0.059(7) Uani 1 1 d . . .
H4 H 0.9674 0.0160 0.2402 0.071 Uiso 1 1 calc R . .
C5 C 0.851(4) -0.0486(15) 0.1646(11) 0.041(5) Uani 1 1 d . . .
H5 H 0.9860 -0.0990 0.1527 0.049 Uiso 1 1 calc R . .
C6 C 0.671(4) -0.0423(17) 0.1358(12) 0.050(6) Uani 1 1 d . . .
H6 H 0.6760 -0.0952 0.1067 0.060 Uiso 1 1 calc R . .
C7 C 0.475(4) 0.0341(17) 0.1440(10) 0.043(5) Uani 1 1 d . . .
H7 H 0.3531 0.0385 0.1188 0.052 Uiso 1 1 calc R . .
C8 C 0.463(3) 0.1066(15) 0.1922(9) 0.029(4) Uani 1 1 d . . .
C9 C -0.073(3) 0.5533(16) 0.3128(10) 0.037(5) Uani 1 1 d . . .
H9 H -0.2102 0.5765 0.3442 0.045 Uiso 1 1 calc R . .
C10 C 0.141(3) 0.5532(14) 0.3458(8) 0.023(4) Uani 1 1 d . . .
C11 C 0.096(4) 0.5943(15) 0.4178(11) 0.042(5) Uani 1 1 d . . .
C12 C 0.277(4) 0.6389(18) 0.5062(11) 0.056(6) Uani 1 1 d . . .
H12A H 0.1803 0.7132 0.5057 0.084 Uiso 1 1 calc R . .
H12B H 0.4276 0.6412 0.5147 0.084 Uiso 1 1 calc R . .
H12C H 0.2163 0.5864 0.5425 0.084 Uiso 1 1 calc R . .
C13 C -0.033(3) 0.6532(16) 0.2554(10) 0.042(5) Uani 1 1 d . . .
H13 H -0.1438 0.7228 0.2640 0.051 Uiso 1 1 calc R . .
C14 C 0.197(3) 0.6504(15) 0.2831(9) 0.029(4) Uani 1 1 d . . .
C15 C 0.223(3) 0.7605(17) 0.3097(10) 0.037(5) Uani 1 1 d . . .
C16 C 0.458(4) 0.8569(19) 0.3416(15) 0.067(8) Uani 1 1 d . . .
H16A H 0.3144 0.9087 0.3482 0.100 Uiso 1 1 calc R . .
H16B H 0.5631 0.8955 0.3105 0.100 Uiso 1 1 calc R . .
H16C H 0.5186 0.8292 0.3859 0.100 Uiso 1 1 calc R . .
C17 C 0.289(3) 0.5649(13) 0.1639(8) 0.022(4) Uani 1 1 d . . .
C18 C 0.380(3) 0.4844(16) 0.1250(10) 0.037(5) Uani 1 1 d . . .
C19 C 0.660(3) 0.3235(15) 0.0685(10) 0.039(5) Uani 1 1 d . . .
C20 C 0.854(4) 0.2390(17) 0.0513(11) 0.049(6) Uani 1 1 d . . .
H20 H 0.9846 0.2249 0.0740 0.058 Uiso 1 1 calc R . .
C21 C 0.840(4) 0.1797(16) 0.0004(10) 0.038(5) Uani 1 1 d . . .
H21 H 0.9694 0.1284 -0.0140 0.046 Uiso 1 1 calc R . .
C22 C 0.654(4) 0.190(2) -0.0297(14) 0.068(8) Uani 1 1 d . . .
H22 H 0.6469 0.1428 -0.0610 0.081 Uiso 1 1 calc R . .
C23 C 0.463(4) 0.2783(14) -0.0127(10) 0.041(5) Uani 1 1 d . . .
H23 H 0.3355 0.2937 -0.0372 0.049 Uiso 1 1 calc R . .
C24 C 0.465(3) 0.3366(13) 0.0363(9) 0.026(4) Uani 1 1 d . . .
O1E O -0.271(4) 0.8759(15) 0.5335(11) 0.115(9) Uani 1 1 d . . .
C1E C 0.127(7) 1.013(4) 0.541(2) 0.16(2) Uani 1 1 d . . .
C2E C -0.053(9) 0.929(4) 0.554(3) 0.168(19) Uiso 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
S1 0.041(3) 0.041(3) 0.045(3) -0.007(2) -0.012(2) -0.006(2)
S2 0.042(3) 0.036(3) 0.045(3) -0.007(2) -0.006(2) -0.007(2)
S3 0.037(3) 0.037(3) 0.044(3) -0.013(2) 0.006(2) -0.011(2)
S4 0.041(3) 0.034(3) 0.039(3) -0.004(2) -0.005(2) -0.008(2)
S5 0.036(3) 0.051(3) 0.028(3) -0.009(2) -0.002(2) -0.002(2)
S6 0.038(3) 0.041(3) 0.038(3) -0.007(2) 0.003(2) -0.005(2)
S7 0.034(3) 0.048(3) 0.033(3) -0.007(2) 0.003(2) -0.006(2)
S8 0.037(3) 0.051(3) 0.031(3) -0.009(2) 0.006(2) -0.010(2)
O1 0.036(8) 0.027(7) 0.058(9) 0.013(7) -0.017(7) -0.003(6)
O2 0.041(8) 0.051(8) 0.033(8) -0.028(7) 0.010(6) -0.018(7)
O3 0.043(9) 0.080(11) 0.050(10) -0.014(8) 0.005(8) -0.020(8)
O4 0.032(8) 0.057(9) 0.032(7) -0.025(7) -0.006(6) -0.004(6)
C1 0.043(12) 0.050(12) 0.006(8) 0.007(8) -0.004(8) -0.015(9)
C2 0.038(12) 0.064(14) 0.012(9) -0.015(9) 0.007(8) -0.009(10)
C3 0.056(14) 0.033(11) 0.020(10) 0.008(8) 0.003(9) 0.008(9)
C4 0.032(12) 0.026(11) 0.11(2) 0.014(13) 0.005(13) -0.007(9)
C5 0.043(13) 0.019(9) 0.051(13) -0.001(9) 0.013(10) -0.001(8)
C6 0.054(15) 0.042(12) 0.061(15) -0.046(11) 0.015(12) -0.009(11)
C7 0.059(15) 0.044(12) 0.028(11) 0.007(10) -0.008(10) -0.022(11)
C8 0.025(10) 0.031(10) 0.029(10) -0.003(8) 0.003(8) -0.007(8)
C9 0.028(11) 0.046(12) 0.035(11) -0.004(10) -0.002(9) -0.004(9)
C10 0.027(10) 0.037(10) 0.008(8) -0.008(7) 0.003(7) -0.012(8)
C11 0.040(13) 0.020(10) 0.060(14) -0.002(9) 0.002(11) -0.004(9)
C12 0.088(19) 0.045(13) 0.045(14) -0.010(11) -0.020(13) -0.022(12)
C13 0.038(12) 0.037(11) 0.040(12) 0.008(9) 0.014(10) -0.006(9)
C14 0.037(11) 0.037(10) 0.017(9) -0.006(8) 0.001(8) -0.013(8)
C15 0.016(10) 0.049(12) 0.045(12) -0.023(10) 0.012(9) -0.006(9)
C16 0.037(13) 0.047(14) 0.12(2) -0.028(15) 0.002(14) -0.014(11)
C17 0.030(10) 0.014(8) 0.020(9) 0.013(7) -0.006(7) -0.009(7)
C18 0.022(10) 0.047(12) 0.040(12) -0.011(10) 0.005(9) -0.008(9)
C19 0.042(13) 0.024(10) 0.042(12) 0.008(9) 0.014(10) -0.008(9)
C20 0.053(14) 0.038(12) 0.046(13) 0.005(10) 0.006(11) -0.008(10)
C21 0.035(12) 0.036(11) 0.044(13) -0.010(10) -0.013(10) -0.002(9)
C22 0.053(16) 0.071(17) 0.075(18) -0.043(14) 0.035(14) -0.005(13)
C23 0.056(14) 0.019(9) 0.043(12) -0.006(9) 0.001(10) -0.002(9)
C24 0.031(10) 0.010(8) 0.031(10) 0.011(8) -0.002(8) 0.001(7)
O1E 0.107(17) 0.057(11) 0.116(17) 0.045(12) 0.029(14) 0.042(11)
C1E 0.15(4) 0.18(4) 0.14(3) -0.14(3) -0.06(3) 0.10(3)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.73(2) . ?
S1 C2 1.75(2) . ?
S2 C8 1.779(17) . ?
S2 C2 1.804(19) . ?
S3 C1 1.742(19) . ?
S3 C9 1.807(19) . ?
S4 C1 1.766(18) . ?
S4 C10 1.771(17) . ?
S5 C18 1.754(18) . ?
S5 C19 1.76(2) . ?
S6 C18 1.759(19) . ?
S6 C24 1.776(17) . ?
S7 C17 1.761(17) . ?
S7 C13 1.81(2) . ?
S8 C17 1.768(17) . ?
S8 C14 1.806(18) . ?
O1 C15 1.21(2) . ?
O2 C15 1.26(2) . ?
O2 C16 1.42(2) . ?
O3 C11 1.27(2) . ?
O4 C11 1.30(2) . ?
O4 C12 1.46(2) . ?
C1 C2 1.34(3) . ?
C3 C4 1.39(3) . ?
C3 C8 1.40(3) . ?
C4 C5 1.44(3) . ?
C5 C6 1.28(3) . ?
C6 C7 1.34(3) . ?
C7 C8 1.39(3) . ?
C9 C10 1.53(2) . ?
C9 C13 1.54(3) . ?
C10 C11 1.55(2) . ?
C10 C14 1.60(2) . ?
C13 C14 1.56(3) . ?
C14 C15 1.58(2) . ?
C17 C18 1.33(2) . ?
C19 C24 1.38(3) . ?
C19 C20 1.42(3) . ?
C20 C21 1.36(3) . ?
C21 C22 1.31(3) . ?
C22 C23 1.43(3) . ?
C23 C24 1.30(2) . ?
O1E C2E 1.72(6) . ?
C1E C2E 1.63(6) . ?
C1E C2E 1.93(5) 2_576 ?
C2E C1E 1.93(5) 2_576 ?

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
C3 S1 C2 96.0(9) . . ?
C8 S2 C2 95.4(9) . . ?
C1 S3 C9 95.1(9) . . ?
C1 S4 C10 94.3(8) . . ?
C18 S5 C19 94.7(9) . . ?
C18 S6 C24 96.9(9) . . ?
C17 S7 C13 94.6(9) . . ?
C17 S8 C14 96.3(8) . . ?
C15 O2 C16 115.1(15) . . ?
C11 O4 C12 118.5(16) . . ?
C2 C1 S3 122.0(15) . . ?
C2 C1 S4 121.3(14) . . ?
S3 C1 S4 114.4(11) . . ?
C1 C2 S1 125.1(14) . . ?
C1 C2 S2 120.9(15) . . ?
S1 C2 S2 114.0(11) . . ?
C4 C3 C8 116(2) . . ?
C4 C3 S1 124.9(19) . . ?
C8 C3 S1 119.1(14) . . ?
C3 C4 C5 120(2) . . ?
C6 C5 C4 118.7(18) . . ?
C5 C6 C7 125.5(19) . . ?
C6 C7 C8 116.7(19) . . ?
C3 C8 C7 123.0(17) . . ?
C3 C8 S2 114.5(13) . . ?
C7 C8 S2 122.5(15) . . ?
C10 C9 C13 91.9(14) . . ?
C10 C9 S3 112.3(12) . . ?
C13 C9 S3 119.5(14) . . ?
C9 C10 C11 115.0(15) . . ?
C9 C10 C14 89.0(13) . . ?
C11 C10 C14 112.3(13) . . ?
C9 C10 S4 114.4(12) . . ?
C11 C10 S4 105.8(11) . . ?
C14 C10 S4 120.1(11) . . ?
O3 C11 O4 127(2) . . ?
O3 C11 C10 122.5(19) . . ?
O4 C11 C10 110.8(16) . . ?
C9 C13 C14 90.3(14) . . ?
C9 C13 S7 122.2(14) . . ?
C14 C13 S7 111.7(12) . . ?
C13 C14 C15 117.5(15) . . ?
C13 C14 C10 88.5(13) . . ?
C15 C14 C10 112.9(13) . . ?
C13 C14 S8 112.3(12) . . ?
C15 C14 S8 108.1(12) . . ?
C10 C14 S8 116.8(12) . . ?
O1 C15 O2 127.1(18) . . ?
O1 C15 C14 119.1(17) . . ?
O2 C15 C14 113.3(15) . . ?
C18 C17 S7 123.7(13) . . ?
C18 C17 S8 124.1(13) . . ?
S7 C17 S8 112.2(9) . . ?
C17 C18 S5 120.5(14) . . ?
C17 C18 S6 124.6(13) . . ?
S5 C18 S6 114.6(10) . . ?
C24 C19 C20 119.2(19) . . ?
C24 C19 S5 119.5(14) . . ?
C20 C19 S5 121.3(17) . . ?
C21 C20 C19 117(2) . . ?
C22 C21 C20 124(2) . . ?
C21 C22 C23 118(2) . . ?
C24 C23 C22 121(2) . . ?
C23 C24 C19 120.5(17) . . ?
C23 C24 S6 125.5(15) . . ?
C19 C24 S6 113.5(14) . . ?
C2E C1E C2E 92(3) . 2_576 ?
O1E C2E C1E 156(4) . . ?
O1E C2E C1E 68(3) . 2_576 ?
C1E C2E C1E 88(3) . 2_576 ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        26.52
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         1.427
_refine_diff_density_min         -1.263
_refine_diff_density_rms         0.383