# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2009


data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'Narcis Avarvari'
_publ_contact_author_email       NARCIS.AVARVARI@UNIV-ANGERS.FR

_publ_section_title              
;
Supramolecular Electroactive Organogel and Conducting
Nanofibers with C3-Symmetrical Architectures
;
loop_
_publ_author_name
'Narcis Avarvari'
'David Amabilino'
'Ion Danila'
'Angel Perez del Pino'
'Josep Puigmarti-Luis'
;
F.Riobe
;
'John Wallis'

# Attachment '2a.cif'

data_2a
_database_code_depnum_ccdc_archive 'CCDC 701238'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            EDT-TTF-CONH-Bypiridine-NH2
_chemical_melting_point          ?
_chemical_formula_moiety         "C19 H14 N4 O S6', 'C H2 Cl2"
_chemical_formula_sum            'C20 H16 Cl2 N4 O S6'
_chemical_formula_weight         591.63

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'
Cl Cl 0.1484 0.1585 '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'
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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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                   11.8333(9)
_cell_length_b                   5.1318(3)
_cell_length_c                   40.565(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.540(10)
_cell_angle_gamma                90.00
_cell_volume                     2458.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      26

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_T_max  0.8708
_exptl_absorpt_process_details   'faceit, STOE'

_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  STOE-IPDS
_diffrn_measurement_method       'Rotation, Phi. incr. = 1.5'
_diffrn_detector_area_resol_mean 6.66
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12385
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.96
_reflns_number_total             4470
_reflns_number_gt                3406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'EXPOSE [STOE-IPDS]'
_computing_cell_refinement       'SELECT, CELL [STOE-IPDS]'
_computing_data_reduction        'INTEGRATE [STOE-IPDS]'
_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^)+(0.1208P)^2^+1.8021P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4470
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1992
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
C1 C 0.0952(5) 1.2702(16) -0.04072(15) 0.095(2) Uani 1 1 d . . .
H1A H 0.0630 1.0986 -0.0448 0.114 Uiso 1 1 calc R . .
H1B H 0.0404 1.3968 -0.0495 0.114 Uiso 1 1 calc R . .
C2 C 0.1981(5) 1.2932(14) -0.05938(16) 0.0879(19) Uani 1 1 d . . .
H2A H 0.2310 1.4640 -0.0551 0.105 Uiso 1 1 calc R . .
H2B H 0.1759 1.2839 -0.0828 0.105 Uiso 1 1 calc R . .
C3 C 0.2162(3) 1.0792(9) 0.01162(12) 0.0541(10) Uani 1 1 d . . .
C4 C 0.2912(3) 0.9837(8) -0.00862(12) 0.0525(10) Uani 1 1 d . . .
C5 C 0.3318(3) 0.7446(8) 0.04686(10) 0.0475(9) Uani 1 1 d . . .
C6 C 0.3691(3) 0.5906(8) 0.07128(11) 0.0484(9) Uani 1 1 d . . .
C7 C 0.3878(3) 0.3306(8) 0.12599(10) 0.0492(9) Uani 1 1 d . . .
C8 C 0.4632(3) 0.2265(9) 0.10646(11) 0.0528(10) Uani 1 1 d . . .
H8 H 0.5064 0.0833 0.1135 0.063 Uiso 1 1 calc R . .
C9 C 0.3635(3) 0.2656(9) 0.16021(11) 0.0524(10) Uani 1 1 d . . .
C10 C 0.4348(3) 0.0009(8) 0.20802(11) 0.0490(9) Uani 1 1 d . . .
C11 C 0.3689(4) 0.1169(10) 0.23118(12) 0.0613(11) Uani 1 1 d . . .
H11 H 0.3182 0.2485 0.2248 0.074 Uiso 1 1 calc R . .
C12 C 0.3789(5) 0.0368(12) 0.26355(13) 0.0736(14) Uani 1 1 d . . .
H12 H 0.3356 0.1129 0.2793 0.088 Uiso 1 1 calc R . .
C13 C 0.4526(5) -0.1536(13) 0.27182(15) 0.0832(16) Uani 1 1 d . . .
H13 H 0.4588 -0.2068 0.2938 0.100 Uiso 1 1 calc R . .
C14 C 0.5116(3) -0.2000(9) 0.21881(11) 0.0515(9) Uani 1 1 d . . .
C15 C 0.5891(3) -0.3369(8) 0.19764(12) 0.0523(10) Uani 1 1 d . . .
C16 C 0.6624(4) -0.5444(9) 0.20884(13) 0.0594(11) Uani 1 1 d . . .
C17 C 0.7298(4) -0.6581(11) 0.18572(17) 0.0775(16) Uani 1 1 d . . .
H17 H 0.7774 -0.7958 0.1921 0.093 Uiso 1 1 calc R . .
C18 C 0.7269(5) -0.5697(13) 0.15396(18) 0.0838(17) Uani 1 1 d . . .
H18 H 0.7718 -0.6469 0.1387 0.101 Uiso 1 1 calc R . .
C19 C 0.6569(4) -0.3655(12) 0.14491(15) 0.0765(15) Uani 1 1 d . . .
H19 H 0.6561 -0.3022 0.1234 0.092 Uiso 1 1 calc R . .
N1 N 0.4305(3) 0.0818(7) 0.17514(9) 0.0519(8) Uani 1 1 d . . .
H1 H 0.4765 0.0045 0.1628 0.062 Uiso 1 1 calc R . .
N2 N 0.5172(4) -0.2713(9) 0.25083(11) 0.0727(12) Uani 1 1 d . . .
N3 N 0.5907(3) -0.2570(8) 0.16598(10) 0.0623(10) Uani 1 1 d . . .
N4 N 0.6710(4) -0.6349(8) 0.24042(12) 0.0723(12) Uani 1 1 d . . .
H4A H 0.7172 -0.7594 0.2458 0.087 Uiso 1 1 calc R . .
H4B H 0.6302 -0.5676 0.2550 0.087 Uiso 1 1 calc R . .
O1 O 0.2879(3) 0.3824(9) 0.17298(9) 0.0812(12) Uani 1 1 d . . .
S1 S 0.11315(12) 1.3154(3) 0.00249(4) 0.0807(5) Uani 1 1 d . . .
S2 S 0.30417(13) 1.0549(3) -0.05028(4) 0.0861(5) Uani 1 1 d . . .
S3 S 0.22022(10) 0.9640(3) 0.05173(3) 0.0608(3) Uani 1 1 d . . .
S4 S 0.38666(9) 0.7500(2) 0.00781(3) 0.0569(3) Uani 1 1 d . . .
S5 S 0.31065(10) 0.5961(2) 0.11018(3) 0.0605(3) Uani 1 1 d . . .
S6 S 0.47894(9) 0.3615(2) 0.06825(3) 0.0586(3) Uani 1 1 d . . .
Cl1 Cl 0.0045(3) 0.7549(7) -0.10458(9) 0.1717(12) Uani 1 1 d . . .
C20 C -0.0678(5) 0.932(2) -0.1306(2) 0.138(4) Uani 1 1 d . . .
H20A H -0.1168 1.0461 -0.1188 0.166 Uiso 1 1 calc R . .
H20B H -0.1155 0.8212 -0.1449 0.166 Uiso 1 1 calc R . .
Cl2 Cl 0.0261(4) 1.1411(7) -0.15728(10) 0.1853(14) 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 0.072(3) 0.142(6) 0.070(4) 0.005(4) 0.000(3) 0.043(4)
C2 0.087(4) 0.102(4) 0.076(4) 0.026(3) 0.010(3) 0.039(3)
C3 0.051(2) 0.055(2) 0.057(3) 0.006(2) 0.0073(18) 0.0177(18)
C4 0.050(2) 0.051(2) 0.057(3) 0.0102(19) 0.0087(17) 0.0144(17)
C5 0.0469(18) 0.048(2) 0.048(2) 0.0002(18) 0.0068(16) 0.0098(16)
C6 0.0506(19) 0.048(2) 0.047(2) 0.0019(18) 0.0072(16) 0.0104(17)
C7 0.0496(19) 0.054(2) 0.045(2) 0.0026(18) 0.0052(16) 0.0065(17)
C8 0.054(2) 0.055(2) 0.051(3) 0.0086(19) 0.0101(17) 0.0160(18)
C9 0.050(2) 0.061(3) 0.046(2) 0.0027(19) 0.0057(16) 0.0053(18)
C10 0.0501(19) 0.052(2) 0.045(2) 0.0050(18) 0.0031(15) -0.0072(17)
C11 0.065(2) 0.071(3) 0.049(3) 0.005(2) 0.0099(19) 0.002(2)
C12 0.079(3) 0.093(4) 0.050(3) 0.003(3) 0.017(2) -0.002(3)
C13 0.109(4) 0.095(4) 0.047(3) 0.020(3) 0.017(3) 0.009(3)
C14 0.054(2) 0.052(2) 0.048(2) 0.0067(19) 0.0004(17) -0.0089(18)
C15 0.055(2) 0.046(2) 0.055(3) 0.0025(19) -0.0059(17) -0.0043(17)
C16 0.055(2) 0.049(2) 0.072(3) 0.001(2) -0.014(2) -0.0070(19)
C17 0.066(3) 0.068(3) 0.097(5) -0.007(3) -0.012(3) 0.013(2)
C18 0.076(3) 0.085(4) 0.091(5) -0.008(3) 0.010(3) 0.027(3)
C19 0.077(3) 0.087(4) 0.067(3) 0.001(3) 0.015(2) 0.023(3)
N1 0.0572(18) 0.060(2) 0.0393(19) 0.0059(16) 0.0075(14) 0.0106(16)
N2 0.092(3) 0.074(3) 0.052(3) 0.017(2) 0.004(2) 0.002(2)
N3 0.064(2) 0.065(2) 0.057(2) 0.0016(19) 0.0052(17) 0.0109(18)
N4 0.081(3) 0.059(2) 0.074(3) 0.008(2) -0.019(2) 0.006(2)
O1 0.075(2) 0.116(3) 0.055(2) 0.018(2) 0.0214(16) 0.043(2)
S1 0.0820(8) 0.0901(10) 0.0707(9) 0.0095(7) 0.0097(6) 0.0525(8)
S2 0.0915(9) 0.1055(11) 0.0645(9) 0.0337(8) 0.0304(7) 0.0556(9)
S3 0.0609(6) 0.0690(7) 0.0539(7) 0.0055(5) 0.0149(5) 0.0288(5)
S4 0.0542(5) 0.0669(7) 0.0509(6) 0.0122(5) 0.0136(4) 0.0270(5)
S5 0.0687(6) 0.0654(7) 0.0490(7) 0.0069(5) 0.0160(5) 0.0282(5)
S6 0.0610(6) 0.0648(7) 0.0518(7) 0.0127(5) 0.0179(5) 0.0261(5)
Cl1 0.166(2) 0.183(3) 0.167(3) -0.014(2) 0.024(2) 0.057(2)
C20 0.055(3) 0.223(11) 0.139(7) -0.071(8) 0.013(4) 0.011(5)
Cl2 0.237(4) 0.140(2) 0.177(3) -0.048(2) -0.005(3) 0.014(2)

_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 1.478(8) . ?
C1 S1 1.768(6) . ?
C2 S2 1.774(5) . ?
C3 C4 1.339(6) . ?
C3 S3 1.729(5) . ?
C3 S1 1.743(4) . ?
C4 S2 1.745(5) . ?
C4 S4 1.751(4) . ?
C5 C6 1.322(6) . ?
C5 S4 1.748(4) . ?
C5 S3 1.756(4) . ?
C6 S5 1.762(4) . ?
C6 S6 1.763(4) . ?
C7 C8 1.340(6) . ?
C7 C9 1.473(6) . ?
C7 S5 1.740(4) . ?
C8 S6 1.718(4) . ?
C9 O1 1.219(5) . ?
C9 N1 1.351(5) . ?
C10 C11 1.391(6) . ?
C10 N1 1.395(5) . ?
C10 C14 1.425(6) . ?
C11 C12 1.374(7) . ?
C12 C13 1.338(8) . ?
C13 N2 1.325(7) . ?
C14 N2 1.347(6) . ?
C14 C15 1.473(6) . ?
C15 N3 1.349(6) . ?
C15 C16 1.429(6) . ?
C16 N4 1.361(6) . ?
C16 C17 1.396(8) . ?
C17 C18 1.364(9) . ?
C18 C19 1.372(8) . ?
C19 N3 1.318(6) . ?
Cl1 C20 1.603(11) . ?
C20 Cl2 1.923(11) . ?

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 116.5(5) . . ?
C1 C2 S2 115.6(5) . . ?
C4 C3 S3 118.1(3) . . ?
C4 C3 S1 127.3(4) . . ?
S3 C3 S1 114.6(2) . . ?
C3 C4 S2 128.2(3) . . ?
C3 C4 S4 117.0(4) . . ?
S2 C4 S4 114.8(2) . . ?
C6 C5 S4 124.3(3) . . ?
C6 C5 S3 121.2(3) . . ?
S4 C5 S3 114.6(2) . . ?
C5 C6 S5 122.1(3) . . ?
C5 C6 S6 124.0(3) . . ?
S5 C6 S6 113.9(2) . . ?
C8 C7 C9 130.0(4) . . ?
C8 C7 S5 116.6(3) . . ?
C9 C7 S5 113.3(3) . . ?
C7 C8 S6 119.1(3) . . ?
O1 C9 N1 125.3(4) . . ?
O1 C9 C7 118.7(4) . . ?
N1 C9 C7 116.0(4) . . ?
C11 C10 N1 122.0(4) . . ?
C11 C10 C14 118.4(4) . . ?
N1 C10 C14 119.6(4) . . ?
C12 C11 C10 119.9(5) . . ?
C13 C12 C11 118.3(5) . . ?
N2 C13 C12 124.4(5) . . ?
N2 C14 C10 119.0(4) . . ?
N2 C14 C15 115.9(4) . . ?
C10 C14 C15 125.0(4) . . ?
N3 C15 C16 119.0(4) . . ?
N3 C15 C14 117.1(4) . . ?
C16 C15 C14 123.9(4) . . ?
N4 C16 C17 118.5(5) . . ?
N4 C16 C15 124.2(5) . . ?
C17 C16 C15 117.3(5) . . ?
C18 C17 C16 120.9(5) . . ?
C17 C18 C19 119.1(6) . . ?
N3 C19 C18 121.5(6) . . ?
C9 N1 C10 128.5(4) . . ?
C13 N2 C14 120.0(5) . . ?
C19 N3 C15 122.2(4) . . ?
C3 S1 C1 99.1(3) . . ?
C4 S2 C2 104.1(2) . . ?
C3 S3 C5 95.17(19) . . ?
C5 S4 C4 95.1(2) . . ?
C7 S5 C6 95.25(19) . . ?
C8 S6 C6 94.84(19) . . ?
Cl1 C20 Cl2 112.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_full 0.927
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.072