# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2003

data_global
_journal_name_full               'New J.Chem.(Nouv.J.Chim.)'

_journal_coden_Cambridge         0440

loop_
_publ_author_name
J.-M.Fabre
B.Sabrina
G.Stephane
H.Katel
O.Iahcene

_publ_contact_author_name        'Prof Jean-Marc Fabre'
_publ_contact_author_address     
;
laboratoire de chimie organique
ENSCM (UNIV-MONTP2)
heterochimie et materiaux organique
8 rue de l'ecole normale
MONTPELLIER
34296
FRANCE
;

_publ_contact_author_email       JMFABRE@CIT.ENSCM.FR

_publ_section_title              
;
SYNTHESIS, REDOX-POWER AND STRUCTURE OF BIS-TTF CONTAINING A PYRIDINE UNIT AS 
POTENTIAL BUILDING BLOCK IN THE CONSTRUCTION OF CONDUCTING-MAGNETIC MATERIALS.
;

data_calcul
_database_code_CSD               192572

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H27 N3 S16'
_chemical_formula_weight         930.50

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   43.3630(16)
_cell_length_b                   5.8730(2)
_cell_length_c                   16.1730(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.367(2)
_cell_angle_gamma                90.00
_cell_volume                     4051.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3772
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      25.350

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1912
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6207
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3700
_reflns_number_gt                2107
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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^ > 2sigma(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^)+(0.0942P)^2^+8.0160P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3700
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.2141
_refine_ls_wR_factor_gt          0.1784
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
N1 N 0.0000 0.5946(8) 0.2500 0.0536(14) Uani 1 2 d S . .
C11 C 0.01699(12) 0.4794(8) 0.2032(3) 0.0620(13) Uani 1 1 d . . .
C10 C 0.03526(12) 0.6153(9) 0.1503(3) 0.0651(14) Uani 1 1 d . . .
H10A H 0.0217 0.7316 0.1207 0.078 Uiso 1 1 calc R . .
H10B H 0.0416 0.5157 0.1086 0.078 Uiso 1 1 calc R . .
C12 C 0.01755(19) 0.2459(9) 0.2015(5) 0.106(3) Uani 1 1 d . . .
H12 H 0.0295 0.1684 0.1684 0.127 Uiso 1 1 calc R . .
C7 C 0.0761(2) 0.275(3) 0.4487(5) 0.219(8) Uani 1 1 d . . .
H7A H 0.0910 0.1519 0.4477 0.262 Uiso 1 1 calc R . .
H7B H 0.0752 0.3020 0.5073 0.262 Uiso 1 1 calc R . .
C13 C 0.0000 0.1300(14) 0.2500 0.170(7) Uani 1 2 d S . .
H13 H 0.0000 -0.0283 0.2500 0.204 Uiso 1 2 calc SR . .
N2 N 0.0350(2) -0.1352(14) 0.4973(5) 0.135(3) Uani 1 1 d . . .
C9 C 0.0486(3) -0.0069(16) 0.4714(5) 0.125(3) Uani 1 1 d . . .
C15 C 0.21272(19) -0.0198(15) -0.0202(5) 0.127(3) Uani 1 1 d . . .
H15A H 0.2225 -0.0476 -0.0681 0.190 Uiso 1 1 calc R . .
H15B H 0.2274 0.0529 0.0231 0.190 Uiso 1 1 calc R . .
H15C H 0.1948 0.0771 -0.0364 0.190 Uiso 1 1 calc R . .
C14 C 0.225119(14) -0.50570(11) 0.31548(4) 0.148(4) Uani 1 1 d . . .
H14A H 0.2400 -0.6232 0.3356 0.221 Uiso 1 1 calc R . .
H14B H 0.2059 -0.5340 0.3351 0.221 Uiso 1 1 calc R . .
H14C H 0.2334 -0.3607 0.3360 0.221 Uiso 1 1 calc R . .
C8 C 0.048111(14) 0.19309(11) 0.41348(4) 0.368(19) Uani 1 1 d R . .
H8A H 0.0473 0.1477 0.3555 0.442 Uiso 1 1 calc R . .
H8B H 0.0312 0.2984 0.4174 0.442 Uiso 1 1 calc R . .
S1 S 0.069808(14) 0.75080(11) 0.20969(4) 0.0796(5) Uani 1 1 d R . .
S2 S 0.109750(14) 0.38502(11) 0.15522(4) 0.0845(5) Uani 1 1 d R . .
S3 S 0.170570(14) -0.18069(11) 0.25533(4) 0.0926(6) Uani 1 1 d R . .
S4 S 0.153758(14) 0.00626(11) 0.08436(4) 0.0888(6) Uani 1 1 d R . .
S5 S 0.131186(14) 0.21176(11) 0.32628(4) 0.1016(7) Uani 1 1 d R . .
S6 S 0.200545(14) -0.28248(11) 0.01781(4) 0.1124(7) Uani 1 1 d R . .
S7 S 0.218061(14) -0.50413(11) 0.20601(4) 0.1090(7) Uani 1 1 d R . .
S8 S 0.095570(14) 0.55468(11) 0.40750(4) 0.1085(7) Uani 1 1 d R . .
C1 C 0.191409(14) -0.28282(11) 0.18016(4) 0.0719(15) Uani 1 1 d R . .
C3 C 0.149663(14) 0.02564(11) 0.18961(4) 0.0714(15) Uani 1 1 d R . .
C6 C 0.094561(14) 0.51557(11) 0.23684(4) 0.0716(15) Uani 1 1 d R . .
C2 C 0.183996(14) -0.19505(11) 0.10275(4) 0.0747(16) Uani 1 1 d R . .
C5 C 0.104151(14) 0.43568(11) 0.31484(4) 0.0820(17) Uani 1 1 d R . .
C4 C 0.132222(14) 0.18305(11) 0.21912(4) 0.0749(16) Uani 1 1 d 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
N1 0.065(3) 0.037(3) 0.066(4) 0.000 0.029(3) 0.000
C11 0.075(3) 0.041(2) 0.079(4) 0.002(2) 0.039(3) 0.007(2)
C10 0.070(3) 0.059(3) 0.075(3) 0.011(3) 0.037(3) 0.010(3)
C12 0.169(7) 0.041(3) 0.138(6) -0.001(3) 0.112(5) 0.009(4)
C7 0.136(8) 0.46(2) 0.079(6) -0.066(10) 0.082(6) -0.068(12)
C13 0.318(19) 0.036(4) 0.213(14) 0.000 0.199(15) 0.000
N2 0.167(7) 0.133(6) 0.123(6) 0.028(5) 0.073(5) 0.022(5)
C9 0.201(11) 0.110(6) 0.072(5) 0.016(5) 0.047(6) 0.060(7)
C15 0.125(6) 0.163(8) 0.106(6) 0.022(5) 0.056(5) 0.029(6)
C14 0.158(8) 0.172(9) 0.114(6) 0.049(6) 0.027(6) 0.074(7)
C8 0.252(19) 0.70(5) 0.149(12) 0.01(2) 0.033(13) 0.27(3)
S1 0.0773(10) 0.0598(8) 0.1106(13) 0.0028(8) 0.0404(9) -0.0005(7)
S2 0.0743(10) 0.1150(13) 0.0686(9) 0.0051(9) 0.0249(7) 0.0310(9)
S3 0.0849(11) 0.1276(15) 0.0689(10) 0.0079(9) 0.0232(8) 0.0403(10)
S4 0.0765(10) 0.1296(14) 0.0595(9) -0.0068(9) 0.0104(7) 0.0371(10)
S5 0.1062(13) 0.1381(16) 0.0645(10) 0.0027(10) 0.0266(9) 0.0488(12)
S6 0.1280(16) 0.1378(17) 0.0793(12) -0.0106(11) 0.0402(11) 0.0474(14)
S7 0.1064(14) 0.1172(15) 0.1070(14) 0.0080(11) 0.0293(11) 0.0499(12)
S8 0.1391(17) 0.1079(14) 0.0924(13) -0.0200(10) 0.0578(12) 0.0098(12)
C1 0.059(3) 0.086(4) 0.073(4) -0.008(3) 0.018(3) 0.012(3)
C3 0.056(3) 0.092(4) 0.067(3) -0.004(3) 0.014(2) 0.015(3)
C6 0.064(3) 0.076(4) 0.082(4) -0.002(3) 0.032(3) 0.009(3)
C2 0.067(3) 0.090(4) 0.069(4) -0.012(3) 0.018(3) 0.010(3)
C5 0.080(4) 0.091(4) 0.083(4) -0.007(3) 0.036(3) 0.012(3)
C4 0.058(3) 0.107(4) 0.064(3) -0.002(3) 0.023(3) 0.017(3)

_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
N1 C11 1.332(5) 2 ?
N1 C11 1.332(5) . ?
C11 C12 1.372(7) . ?
C11 C10 1.496(6) . ?
C10 S1 1.812(6) . ?
C12 C13 1.368(7) . ?
C7 C8 1.334(10) . ?
C7 S8 2.015(14) . ?
C13 C12 1.368(7) 2 ?
N2 C9 1.087(11) . ?
C9 C8 1.500(9) . ?
C15 S6 1.776(8) . ?
C14 S7 1.7416 . ?
S1 C6 1.7561 . ?
S2 C4 1.7499 . ?
S2 C6 1.7541 . ?
S3 C1 1.7463 . ?
S3 C3 1.7530 . ?
S4 C3 1.7467 . ?
S4 C2 1.7508 . ?
S5 C5 1.7493 . ?
S5 C4 1.7499 . ?
S6 C2 1.7379 . ?
S7 C1 1.7395 . ?
S8 C5 1.7530 . ?
C1 C2 1.3386 . ?
C3 C4 1.3358 . ?
C6 C5 1.3401 . ?

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
C11 N1 C11 119.0(5) 2 . ?
N1 C11 C12 122.1(5) . . ?
N1 C11 C10 117.3(4) . . ?
C12 C11 C10 120.6(5) . . ?
C11 C10 S1 113.8(4) . . ?
C13 C12 C11 118.2(6) . . ?
C8 C7 S8 123.8(9) . . ?
C12 C13 C12 120.3(8) 2 . ?
N2 C9 C8 146.7(11) . . ?
C7 C8 C9 96.1(8) . . ?
C6 S1 C10 101.35(16) . . ?
C4 S2 C6 95.5 . . ?
C1 S3 C3 95.2 . . ?
C3 S4 C2 94.8 . . ?
C5 S5 C4 96.0 . . ?
C2 S6 C15 102.0(2) . . ?
C1 S7 C14 103.6 . . ?
C5 S8 C7 97.1(3) . . ?
C2 C1 S7 123.4 . . ?
C2 C1 S3 116.8 . . ?
S7 C1 S3 119.6 . . ?
C4 C3 S4 123.8 . . ?
C4 C3 S3 121.7 . . ?
S4 C3 S3 114.4 . . ?
C5 C6 S2 117.4 . . ?
C5 C6 S1 125.7 . . ?
S2 C6 S1 116.8 . . ?
C1 C2 S6 124.2 . . ?
C1 C2 S4 117.7 . . ?
S6 C2 S4 117.9 . . ?
C6 C5 S5 116.8 . . ?
C6 C5 S8 126.0 . . ?
S5 C5 S8 116.8 . . ?
C3 C4 S2 123.3 . . ?
C3 C4 S5 122.5 . . ?
S2 C4 S5 114.1 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.068