# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 1145/183

data_global

_publ_contact_author               'Andrei S.Batsanov'
_publ_contact_author_email          a.s.batsanov@durham.ac.uk

loop_
_publ_author_name
 'Bryce, Martin R.'
 'Moore, Adrian J.'
 'Batsanov, Andrei S.' 
 'Howard, Judith A. K.' 
 'Petty, Michael C.'
 'Williams, Geoffrey'
 'Rotello, Vincent'
 'Cuello, Alejandro'
_journal_name_full             'Journal of Materials Chemistry'
_journal_volume                    '?'
_journal_page_first                '?'
_journal_page_last                 '?'
_journal_year                      '1999'
_ccdc_journal_depnumber            '?'

_publ_section_title
;
 4-Ethoxycarbonyl-4',5,5'-trimethyltetrathiafulvalene and its radical
 cation: Langmuir-Blodgett film studies, EPR spectra and the X-ray 
 crystal structure of (Me3TTF-CO2Et)2.TCNQ complex.
;
#======================================================================
data_(10)2.TCNQ 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 4-ethoxycarbonyl-4',5,5'-trimethyltetrathiafulvalene 
 7,7,8,8-tetracyanoquinodimethane, 2:1 complex 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          
 '(C12 H14 O2 S4)2,C12 H4 N4' 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C36 H32 N4 O4 S8' 
_chemical_formula_weight          841.14 
_chemical_melting_point           ? 
_chemical_compound_source         ? 

_ccdc_compound_id                  '(10)~2~.TCNQ'
_ccdc_biological_activity          '?'
_ccdc_polymorph                    '?'
_ccdc_disorder                     
;
 none
;
_ccdc_comments                     '?'

 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'    .0033    .0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'    .0000    .0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'    .0061    .0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'    .0106    .0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'S'  'S'    .1246    .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                    7.686(3) 
_cell_length_b                    11.454(4) 
_cell_length_c                    11.617(5) 
_cell_angle_alpha                 76.59(2) 
_cell_angle_beta                  80.25(2) 
_cell_angle_gamma                 84.48(3) 
_cell_volume                      978.8(7) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     20 
_cell_measurement_theta_min       11 
_cell_measurement_theta_max       12 
 
_exptl_crystal_description        'Lump' 
_exptl_crystal_colour             Black 
_exptl_crystal_size_max           0.4 
_exptl_crystal_size_mid           0.4 
_exptl_crystal_size_min           0.25 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.427 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              436 
_exptl_absorpt_coefficient_mu     0.500 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.7785 
_exptl_absorpt_correction_T_max   0.8345 
 
_exptl_special_details 
; 
 Three sets of \w scans (each scan 0.3\%) at different 2\q and \f 
 angles, nominally covered over a hemisphere of reciprocal space. The
 first 50 scans were repeated at the end of the experiment, revealing
 no appreciable decay of intensities.  
; 
 
_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        'SMART 1K CCD detector' 
_diffrn_measurement_method        '\w scans' 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             3745 
_diffrn_reflns_av_R_equivalents   0.0185 
_diffrn_reflns_av_sigmaI/netI     0.0253 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        7 
_diffrn_reflns_theta_min          1.82 
_diffrn_reflns_theta_max          23.25 
_reflns_number_total              2701 
_reflns_number_observed           2495 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        SMART 
_computing_cell_refinement        SMART 
_computing_data_reduction         SAINT 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     SHELXTL-Plus 
_computing_publication_material   SHELXL-93 
 
_refine_special_details 
; 
 Refinement on F^2^ for ALL reflections.  Weighted R-factors 
 wR and all goodnesses 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 observed 
criterion 
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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. 
 Hydrogen atoms refinement: methyl groups as rotating bodies with common 
 refined U_iso for 3 hydrogens; methylene H - refU; TCNQ hydrogens - 
refall.
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme 
 'calc w=1/[\s^2^(Fo^2^)+(0.047P)^2^+0.36P] 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     ? 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.021(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          2701 
_refine_ls_number_parameters      254 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0395 
_refine_ls_R_factor_obs           0.0364 
_refine_ls_wR_factor_all          0.0989 
_refine_ls_wR_factor_obs          0.0952 
_refine_ls_goodness_of_fit_all    1.078 
_refine_ls_goodness_of_fit_obs    1.084 
_refine_ls_restrained_S_all       1.078 
_refine_ls_restrained_S_obs       1.084 
_refine_ls_shift/esd_max          0.060 
_refine_ls_shift/esd_mean         0.001 
 
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
S1 S 0.17729(8) 0.30069(6) 0.54098(5) 0.0606(2) Uani 1 d . . 
S2 S -0.12332(8) 0.37188(6) 0.40894(6) 0.0659(2) Uani 1 d . . 
S3 S 0.43557(9) 0.45061(6) 0.32360(6) 0.0671(2) Uani 1 d . . 
S4 S 0.14332(9) 0.53370(6) 0.18767(6) 0.0645(2) Uani 1 d . . 
O1 O 0.1259(2) 0.1564(2) 0.76451(14) 0.0693(5) Uani 1 d . . 
O2 O -0.1654(3) 0.1293(2) 0.7962(2) 0.0844(6) Uani 1 d . . 
C1 C 0.1026(3) 0.3812(2) 0.4096(2) 0.0572(6) Uani 1 d . . 
C2 C -0.0305(3) 0.2507(2) 0.6128(2) 0.0552(6) Uani 1 d . . 
C3 C -0.1696(3) 0.2832(2) 0.5526(2) 0.0590(6) Uani 1 d . . 
C4 C 0.2114(3) 0.4458(2) 0.3182(2) 0.0567(6) Uani 1 d . . 
C5 C 0.4847(3) 0.5505(2) 0.1855(2) 0.0604(6) Uani 1 d . . 
C6 C 0.3510(3) 0.5891(2) 0.1236(2) 0.0599(6) Uani 1 d . . 
C7 C -0.0377(4) 0.1731(2) 0.7334(2) 0.0613(6) Uani 1 d . . 
C8 C -0.3583(3) 0.2503(3) 0.5930(3) 0.0751(8) Uani 1 d . . 
H8A H -0.3970(11) 0.2161(20) 0.5343(11) 0.139(8) Uiso 1 d R . 
H8B H -0.4318(6) 0.3211(5) 0.6027(21) 0.139(8) Uiso 1 d R . 
H8C H -0.3666(6) 0.1927(17) 0.6680(11) 0.139(8) Uiso 1 d R . 
C9 C 0.6742(4) 0.5821(3) 0.1497(3) 0.0818(8) Uani 1 d . . 
H9A H 0.7475(4) 0.5095(3) 0.1485(17) 0.105(6) Uiso 1 d R . 
H9B H 0.7071(8) 0.6218(15) 0.2064(10) 0.105(6) Uiso 1 d R . 
H9C H 0.6898(6) 0.6343(14) 0.0715(8) 0.105(6) Uiso 1 d R . 
C10 C 0.3584(4) 0.6777(2) 0.0047(2) 0.0766(8) Uani 1 d . . 
H10A H 0.3305(32) 0.7576(3) 0.0175(2) 0.149(9) Uiso 1 d R . 
H10B H 0.2742(23) 0.6582(14) -0.0393(9) 0.149(9) Uiso 1 d R . 
H10C H 0.4750(10) 0.6733(16) -0.0401(9) 0.149(9) Uiso 1 d R . 
C11 C 0.1402(4) 0.0791(3) 0.8812(2) 0.0865(9) Uani 1 d . . 
H11A H 0.0959(4) 0.0011(3) 0.8868(2) 0.129(13) Uiso 1 d R . 
H11B H 0.0702(4) 0.1151(3) 0.9432(2) 0.120(12) Uiso 1 d R . 
C12 C 0.3276(5) 0.0654(3) 0.8979(3) 0.1053(12) Uani 1 d . . 
H12A H 0.3392(7) 0.0125(17) 0.9738(10) 0.138(8) Uiso 1 d R . 
H12B H 0.3690(10) 0.1424(4) 0.8958(22) 0.138(8) Uiso 1 d R . 
H12C H 0.3966(7) 0.0320(20) 0.8350(12) 0.138(8) Uiso 1 d R . 
C13 C -0.1049(3) 0.9313(2) -0.3993(2) 0.0520(6) Uani 1 d . . 
C14 C -0.1788(3) 0.9924(2) -0.5042(2) 0.0541(6) Uani 1 d . . 
H14 H -0.2951(34) 0.9829(21) -0.5038(21) 0.061(7) Uiso 1 d . . 
C15 C -0.0794(3) 1.0579(2) -0.5996(2) 0.0538(6) Uani 1 d . . 
H15 H -0.1267(28) 1.0922(19) -0.6655(21) 0.049(6) Uiso 1 d . . 
C16 C -0.2072(3) 0.8641(2) -0.3012(2) 0.0580(6) Uani 1 d . . 
C17 C -0.1350(4) 0.8023(2) -0.1966(2) 0.0650(6) Uani 1 d . . 
C18 C -0.3919(4) 0.8545(2) -0.2990(2) 0.0664(7) Uani 1 d . . 
N1 N -0.0744(4) 0.7530(2) -0.1145(2) 0.0886(8) Uani 1 d . . 
N2 N -0.5389(3) 0.8491(3) -0.2997(2) 0.0928(8) Uani 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 0.0589(4) 0.0659(4) 0.0529(4) 0.0030(3) -0.0131(3) -0.0147(3) 
S2 0.0532(4) 0.0731(4) 0.0647(4) 0.0014(3) -0.0120(3) -0.0054(3) 
S3 0.0584(4) 0.0686(4) 0.0675(4) 0.0120(3) -0.0203(3) -0.0172(3) 
S4 0.0590(4) 0.0691(4) 0.0594(4) 0.0055(3) -0.0166(3) -0.0093(3) 
O1 0.0809(13) 0.0745(11) 0.0465(9) 0.0035(8) -0.0098(8) -0.0162(9) 
O2 0.0826(13) 0.0985(14) 0.0616(12) -0.0017(10) 0.0080(10) -0.0261(11) 
C1 0.0570(14) 0.0561(13) 0.0559(14) -0.0020(11) -0.0137(11) -0.0064(11) 
C2 0.0595(14) 0.0538(13) 0.0497(13) -0.0086(10) -0.0022(11) -0.0084(11) 
C3 0.0581(14) 0.0575(14) 0.0577(14) -0.0110(11) 0.0007(11) -0.0055(11) 
C4 0.0521(13) 0.0571(13) 0.0583(14) -0.0010(11) -0.0137(11) -0.0102(10) 
C5 0.0612(15) 0.0580(14) 0.0579(14) -0.0015(11) -0.0085(12) -0.0124(11) 
C6 0.067(2) 0.0567(14) 0.0511(14) -0.0010(11) -0.0054(12) -0.0112(12) 
C7 0.071(2) 0.0599(14) 0.0524(14) -0.0140(11) -0.0023(13) -0.0106(13) 
C8 0.0520(15) 0.086(2) 0.081(2) -0.0131(15) 0.0024(13) -0.0038(13) 
C9 0.070(2) 0.088(2) 0.080(2) 0.003(2) -0.0095(15) -0.025(2) 
C10 0.087(2) 0.075(2) 0.058(2) 0.0078(13) -0.0105(14) -0.0127(15) 
C11 0.112(3) 0.093(2) 0.049(2) 0.0081(15) -0.019(2) -0.024(2) 
C12 0.130(3) 0.098(2) 0.079(2) 0.001(2) -0.033(2) 0.014(2) 
C13 0.0524(13) 0.0533(13) 0.0517(13) -0.0129(11) -0.0107(11) -0.0014(10) 
C14 0.0474(14) 0.0564(14) 0.0601(15) -0.0127(11) -0.0136(11) -0.0024(11) 
C15 0.0561(14) 0.0545(13) 0.0527(14) -0.0092(11) -0.0186(12) -0.0009(11) 
C16 0.0553(14) 0.0641(14) 0.0543(14) -0.0115(11) -0.0094(11) -0.0035(11) 
C17 0.067(2) 0.073(2) 0.0528(15) -0.0061(13) -0.0092(13) -0.0127(13) 
C18 0.062(2) 0.073(2) 0.058(2) -0.0045(12) -0.0071(12) -0.0051(13) 
N1 0.092(2) 0.106(2) 0.0621(15) 0.0034(14) -0.0196(14) -0.0211(15) 
N2 0.056(2) 0.117(2) 0.095(2) -0.002(2) -0.0117(13) -0.0074(14) 
 
_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 C1 1.747(2) . ? 
S1 C2 1.754(2) . ? 
S2 C3 1.739(3) . ? 
S2 C1 1.751(2) . ? 
S3 C4 1.741(2) . ? 
S3 C5 1.747(2) . ? 
S4 C4 1.746(2) . ? 
S4 C6 1.755(2) . ? 
O1 C7 1.350(3) . ? 
O1 C11 1.452(3) . ? 
O2 C7 1.196(3) . ? 
C1 C4 1.352(4) . ? 
C2 C3 1.352(3) . ? 
C2 C7 1.470(3) . ? 
C3 C8 1.503(3) . ? 
C5 C6 1.335(3) . ? 
C5 C9 1.501(4) . ? 
C6 C10 1.508(3) . ? 
C11 C12 1.474(4) . ? 
C13 C16 1.384(3) . ? 
C13 C15 1.432(3) 2_574 ? 
C13 C14 1.435(3) . ? 
C14 C15 1.346(3) . ? 
C15 C13 1.432(3) 2_574 ? 
C16 C17 1.427(4) . ? 
C16 C18 1.430(4) . ? 
C17 N1 1.138(3) . ? 
C18 N2 1.139(3) . ? 
 
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 
C1 S1 C2 95.26(11) . . ? 
C3 S2 C1 96.73(12) . . ? 
C4 S3 C5 96.36(11) . . ? 
C4 S4 C6 95.88(11) . . ? 
C7 O1 C11 115.7(2) . . ? 
C4 C1 S1 122.0(2) . . ? 
C4 C1 S2 123.9(2) . . ? 
S1 C1 S2 114.07(14) . . ? 
C3 C2 C7 125.2(2) . . ? 
C3 C2 S1 118.1(2) . . ? 
C7 C2 S1 116.7(2) . . ? 
C2 C3 C8 128.3(2) . . ? 
C2 C3 S2 115.8(2) . . ? 
C8 C3 S2 115.9(2) . . ? 
C1 C4 S3 121.8(2) . . ? 
C1 C4 S4 124.4(2) . . ? 
S3 C4 S4 113.86(13) . . ? 
C6 C5 C9 127.4(2) . . ? 
C6 C5 S3 116.8(2) . . ? 
C9 C5 S3 115.7(2) . . ? 
C5 C6 C10 126.9(2) . . ? 
C5 C6 S4 117.1(2) . . ? 
C10 C6 S4 116.1(2) . . ? 
O2 C7 O1 123.7(2) . . ? 
O2 C7 C2 126.9(3) . . ? 
O1 C7 C2 109.4(2) . . ? 
O1 C11 C12 108.5(3) . . ? 
C16 C13 C15 121.2(2) . 2_574 ? 
C16 C13 C14 121.5(2) . . ? 
C15 C13 C14 117.3(2) 2_574 . ? 
C15 C14 C13 121.5(2) . . ? 
C14 C15 C13 121.2(2) . 2_574 ? 
C13 C16 C17 122.0(2) . . ? 
C13 C16 C18 121.4(2) . . ? 
C17 C16 C18 116.6(2) . . ? 
N1 C17 C16 178.7(3) . . ? 
N2 C18 C16 178.3(3) . . ? 
 
_refine_diff_density_max     .233 
_refine_diff_density_min    -.196 
_refine_diff_density_rms     .042