# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2010 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address Y.Lakhdar ; Institut des Sciences et Technologies Mol\'eculaires, CNRS-Universit\'e d'Angers, 49045 Angers, France ; C.Meziere ; Institut des Sciences et Technologies Mol\'eculaires, CNRS-Universit\'e d'Angers, 49045 Angers, France ; L.Zorina ; Institute of Solid State Physics, RAS, 142432 Chernogolovka, Russia ; M.Giffard ; Institut des Sciences et Technologies Mol\'eculaires, CNRS-Universit\'e d'Angers, 49045 Angers, France ; P.Batail ; Institut des Sciences et Technologies Mol\'eculaires, CNRS-Universit\'e d'Angers, 49045 Angers, France ; E.Canadell ; Institut de Ci\`encia de Materials de Barcelona (ICMAB-CSIC), Campus de la UAB, E-08193 Bellaterra, Spain ; ; P.Auban-Senzier ; ; Laboratoire de Physique des Solides, CNRS-Universit\'e de Paris-Sud, 91405 Orsay, France ; C.Pasquier ; Laboratoire de Physique des Solides, CNRS-Universit\'e de Paris-Sud, 91405 Orsay, France ; D.Jerome ; Laboratoire de Physique des Solides, CNRS-Universit\'e de Paris-Sud, 91405 Orsay, France ; B.Nafradi ; Institut de Physique de la Mati\`ere Complexe, Ecole Polytechnique F\'ed\'erale de Lausanne (EPFL), 1015 Lausanne, Switzerland ; L.Forro ; Institut de Physique de la Mati\`ere Complexe, Ecole Polytechnique F\'ed\'erale de Lausanne (EPFL), 1015 Lausanne, Switzerland ; _publ_contact_author_address ; Institut des Sciences et Technologies Mol\'eculaires, CNRS-Universit\'e d'Angers, 49045 Angers, France ; _publ_contact_author_email patrick.batail@univ-angers.fr _publ_contact_author_name 'Dr. Patrick Batail' data_beta-(EDT-TTF-I2)2Fumarate _database_code_depnum_ccdc_archive 'CCDC 790256' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H4 I2 S6), C4 H3 O4' _chemical_formula_sum 'C20 H11 I4 O4 S12' _chemical_formula_weight 1207.61 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' I I -0.4742 1.8119 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1576(4) _cell_length_b 13.1699(13) _cell_length_c 15.4841(9) _cell_angle_alpha 78.710(7) _cell_angle_beta 80.782(5) _cell_angle_gamma 88.271(6) _cell_volume 1610.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1134 _exptl_absorpt_coefficient_mu 4.679 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4357 _exptl_absorpt_correction_T_max 0.7513 _exptl_absorpt_process_details sadabs _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 'Bruker Nonius KappaCCD' _diffrn_measurement_method 'combined \f and \w-scans' _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_standards_decay_% 0 _diffrn_reflns_number 49416 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 30.00 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 9373 _reflns_number_gt 6388 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact GbR 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0193P)^2^+0.5898P] 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 9373 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0557 _refine_ls_wR_factor_gt 0.0489 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.885 _refine_diff_density_min -1.110 _refine_diff_density_rms 0.108 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 I11 I 0.28174(2) 0.841090(14) 0.180755(11) 0.02619(5) Uani 1 1 d . . . I12 I 0.65035(2) 0.680246(15) 0.253710(12) 0.03324(5) Uani 1 1 d . . . S11 S 0.20634(8) 0.98360(5) 0.55957(4) 0.02854(15) Uani 1 1 d . . . S12 S 0.48087(8) 0.85494(5) 0.62131(4) 0.02700(15) Uani 1 1 d . . . S13 S 0.25982(8) 0.89523(5) 0.37851(4) 0.02612(15) Uani 1 1 d . . . S14 S 0.53977(8) 0.76821(5) 0.43553(4) 0.02682(15) Uani 1 1 d . . . S15 S 0.12314(8) 1.07185(5) 0.72174(5) 0.03057(16) Uani 1 1 d . . . S16 S 0.45136(8) 0.91851(6) 0.79462(4) 0.02965(16) Uani 1 1 d . . . C11 C 0.3618(3) 0.8949(2) 0.53700(16) 0.0246(6) Uani 1 1 d . . . C12 C 0.3866(3) 0.85744(19) 0.45990(16) 0.0234(6) Uani 1 1 d . . . C13 C 0.2518(3) 0.99134(19) 0.66448(16) 0.0239(6) Uani 1 1 d . . . C14 C 0.3783(3) 0.93220(19) 0.69286(16) 0.0229(5) Uani 1 1 d . . . C15 C 0.3685(3) 0.82709(19) 0.30239(15) 0.0219(5) Uani 1 1 d . . . C16 C 0.4964(3) 0.7692(2) 0.32838(16) 0.0239(6) Uani 1 1 d . . . C17 C 0.1370(3) 1.0059(2) 0.83487(17) 0.0308(6) Uani 1 1 d . . . H17A H 0.0678 1.0417 0.8764 0.037 Uiso 1 1 calc R . . H17B H 0.0943 0.9360 0.8439 0.037 Uiso 1 1 calc R . . C18 C 0.3133(3) 1.0010(2) 0.85481(17) 0.0278(6) Uani 1 1 d . . . H18A H 0.3105 0.9761 0.9183 0.033 Uiso 1 1 calc R . . H18B H 0.3589 1.0706 0.8403 0.033 Uiso 1 1 calc R . . I31 I 0.20371(2) 0.668964(14) 0.817590(11) 0.02772(5) Uani 1 1 d . . . I32 I -0.15080(2) 0.824871(14) 0.736834(12) 0.03297(5) Uani 1 1 d . . . S31 S 0.30009(8) 0.51470(6) 0.43816(4) 0.02956(16) Uani 1 1 d . . . S32 S 0.02482(8) 0.64198(5) 0.37513(4) 0.02777(15) Uani 1 1 d . . . S33 S 0.23930(8) 0.60258(5) 0.62068(4) 0.02644(15) Uani 1 1 d . . . S34 S -0.03857(8) 0.72950(5) 0.55939(4) 0.02740(15) Uani 1 1 d . . . S35 S 0.38693(9) 0.42600(6) 0.27623(5) 0.03303(17) Uani 1 1 d . . . S36 S 0.05847(9) 0.57635(6) 0.20203(5) 0.03188(16) Uani 1 1 d . . . C31 C 0.1429(3) 0.60235(19) 0.45990(16) 0.0231(6) Uani 1 1 d . . . C32 C 0.1165(3) 0.63924(19) 0.53719(16) 0.0239(6) Uani 1 1 d . . . C33 C 0.2570(3) 0.5071(2) 0.33239(16) 0.0245(6) Uani 1 1 d . . . C34 C 0.1304(3) 0.5652(2) 0.30339(16) 0.0235(6) Uani 1 1 d . . . C35 C 0.1293(3) 0.6741(2) 0.69443(16) 0.0235(6) Uani 1 1 d . . . C36 C 0.0027(3) 0.73128(19) 0.66622(16) 0.0233(5) Uani 1 1 d . . . C37 C 0.3720(3) 0.4903(3) 0.16208(18) 0.0432(8) Uani 1 1 d . . . H37A H 0.4176 0.5596 0.1518 0.052 Uiso 1 1 calc R . . H37B H 0.4394 0.4527 0.1213 0.052 Uiso 1 1 calc R . . C38 C 0.1999(4) 0.4977(3) 0.14154(19) 0.0441(8) Uani 1 1 d . . . H38A H 0.1543 0.4283 0.1533 0.053 Uiso 1 1 calc R . . H38B H 0.2049 0.5251 0.0783 0.053 Uiso 1 1 calc R . . C1 C -0.0482(3) 0.7259(2) 0.00781(17) 0.0294(6) Uani 1 1 d . . . H1 H -0.0545 0.6548 0.0115 0.035 Uiso 1 1 calc R . . C2 C -0.1846(3) 0.7800(2) 0.00042(17) 0.0319(6) Uani 1 1 d . . . H2 H -0.1820 0.8511 -0.0020 0.038 Uiso 1 1 calc R . . C3 C 0.1172(3) 0.7707(2) 0.01080(17) 0.0293(6) Uani 1 1 d . . . O1 O 0.2433(2) 0.71831(16) -0.01270(12) 0.0377(5) Uani 1 1 d . . . O2 O 0.1211(2) 0.85421(16) 0.03686(13) 0.0384(5) Uani 1 1 d . . . C4 C -0.3443(3) 0.7300(3) -0.00415(18) 0.0329(7) Uani 1 1 d . . . O3 O -0.4644(2) 0.79832(16) -0.01602(13) 0.0417(5) Uani 1 1 d . . . H3 H -0.5518 0.7680 -0.0135 0.063 Uiso 1 1 calc R . . O4 O -0.3603(3) 0.63834(19) 0.00338(17) 0.0595(7) 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 I11 0.02469(9) 0.03691(11) 0.01940(9) -0.00937(7) -0.00601(7) 0.00093(8) I12 0.03126(10) 0.03848(11) 0.03497(11) -0.01976(9) -0.00627(8) 0.00942(9) S11 0.0285(3) 0.0375(4) 0.0230(3) -0.0111(3) -0.0096(3) 0.0110(3) S12 0.0285(3) 0.0348(4) 0.0207(3) -0.0104(3) -0.0085(3) 0.0108(3) S13 0.0257(3) 0.0344(4) 0.0205(3) -0.0089(3) -0.0075(3) 0.0092(3) S14 0.0276(3) 0.0330(4) 0.0222(3) -0.0084(3) -0.0086(3) 0.0087(3) S15 0.0311(4) 0.0348(4) 0.0290(4) -0.0145(3) -0.0057(3) 0.0100(3) S16 0.0294(3) 0.0414(4) 0.0222(3) -0.0129(3) -0.0091(3) 0.0070(3) C11 0.0235(13) 0.0291(15) 0.0219(14) -0.0070(11) -0.0040(11) 0.0054(11) C12 0.0247(13) 0.0269(14) 0.0196(13) -0.0064(11) -0.0046(10) 0.0048(11) C13 0.0242(13) 0.0271(14) 0.0212(13) -0.0069(11) -0.0037(11) 0.0021(11) C14 0.0238(13) 0.0269(14) 0.0190(13) -0.0072(11) -0.0029(10) -0.0015(11) C15 0.0235(12) 0.0288(14) 0.0153(12) -0.0071(11) -0.0046(10) -0.0001(11) C16 0.0253(13) 0.0276(14) 0.0204(13) -0.0075(11) -0.0047(11) 0.0008(11) C17 0.0269(14) 0.0429(17) 0.0237(14) -0.0131(13) 0.0008(11) 0.0003(13) C18 0.0287(14) 0.0362(16) 0.0210(14) -0.0135(12) -0.0009(11) -0.0023(12) I31 0.02482(9) 0.04013(11) 0.02062(9) -0.01025(8) -0.00582(7) 0.00213(8) I32 0.02986(10) 0.03737(11) 0.03746(12) -0.02026(9) -0.00845(8) 0.01018(8) S31 0.0303(3) 0.0377(4) 0.0242(4) -0.0118(3) -0.0098(3) 0.0115(3) S32 0.0302(3) 0.0342(4) 0.0217(3) -0.0105(3) -0.0082(3) 0.0104(3) S33 0.0279(3) 0.0334(4) 0.0206(3) -0.0102(3) -0.0074(3) 0.0104(3) S34 0.0286(3) 0.0332(4) 0.0234(3) -0.0098(3) -0.0092(3) 0.0091(3) S35 0.0327(4) 0.0377(4) 0.0328(4) -0.0171(3) -0.0068(3) 0.0111(3) S36 0.0355(4) 0.0415(4) 0.0228(4) -0.0128(3) -0.0105(3) 0.0079(3) C31 0.0239(13) 0.0261(14) 0.0207(13) -0.0073(11) -0.0050(10) 0.0041(11) C32 0.0258(13) 0.0282(14) 0.0192(13) -0.0066(11) -0.0067(11) 0.0041(11) C33 0.0257(13) 0.0282(14) 0.0212(13) -0.0089(11) -0.0038(11) 0.0001(12) C34 0.0241(13) 0.0290(14) 0.0189(13) -0.0076(11) -0.0041(11) -0.0008(12) C35 0.0225(13) 0.0301(15) 0.0195(13) -0.0081(11) -0.0032(10) -0.0024(11) C36 0.0229(13) 0.0267(14) 0.0221(13) -0.0091(11) -0.0040(10) 0.0021(11) C37 0.0355(16) 0.070(2) 0.0252(16) -0.0180(15) 0.0025(13) -0.0002(16) C38 0.0492(19) 0.059(2) 0.0291(17) -0.0211(15) -0.0092(14) 0.0155(17) C1 0.0230(13) 0.0441(17) 0.0227(14) -0.0099(12) -0.0028(11) -0.0066(13) C2 0.0220(13) 0.0470(18) 0.0294(15) -0.0142(13) -0.0027(11) -0.0033(13) C3 0.0237(14) 0.0466(18) 0.0183(13) -0.0045(12) -0.0078(11) 0.0004(13) O1 0.0204(10) 0.0567(13) 0.0396(12) -0.0173(10) -0.0060(9) 0.0035(10) O2 0.0322(11) 0.0505(13) 0.0381(12) -0.0173(10) -0.0117(9) 0.0015(10) C4 0.0213(14) 0.054(2) 0.0279(15) -0.0184(14) -0.0029(11) 0.0020(14) O3 0.0201(10) 0.0581(14) 0.0488(13) -0.0116(11) -0.0090(9) -0.0014(10) O4 0.0316(12) 0.0566(16) 0.097(2) -0.0306(15) -0.0090(12) -0.0022(12) _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 I11 C15 2.089(2) . ? I12 C16 2.065(2) . ? S11 C11 1.739(2) . ? S11 C13 1.745(2) . ? S12 C11 1.741(2) . ? S12 C14 1.748(3) . ? S13 C15 1.735(2) . ? S13 C12 1.745(2) . ? S14 C12 1.738(2) . ? S14 C16 1.749(2) . ? S15 C13 1.736(3) . ? S15 C17 1.816(3) . ? S16 C14 1.748(2) . ? S16 C18 1.818(3) . ? C11 C12 1.363(3) . ? C13 C14 1.352(3) . ? C15 C16 1.341(3) . ? C17 C18 1.516(3) . ? I31 C35 2.080(2) . ? I32 C36 2.068(2) . ? S31 C31 1.736(2) . ? S31 C33 1.751(2) . ? S32 C31 1.740(2) . ? S32 C34 1.755(3) . ? S33 C35 1.743(3) . ? S33 C32 1.746(2) . ? S34 C36 1.745(2) . ? S34 C32 1.750(2) . ? S35 C33 1.738(3) . ? S35 C37 1.826(3) . ? S36 C34 1.740(2) . ? S36 C38 1.801(3) . ? C31 C32 1.361(3) . ? C33 C34 1.349(3) . ? C35 C36 1.340(3) . ? C37 C38 1.484(4) . ? C1 C2 1.312(4) . ? C1 C3 1.500(3) . ? C2 C4 1.495(4) . ? C3 O2 1.246(3) . ? C3 O1 1.265(3) . ? C4 O4 1.199(3) . ? C4 O3 1.320(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 C11 S11 C13 95.58(12) . . ? C11 S12 C14 95.37(12) . . ? C15 S13 C12 95.42(11) . . ? C12 S14 C16 94.75(12) . . ? C13 S15 C17 98.74(12) . . ? C14 S16 C18 103.36(12) . . ? C12 C11 S11 122.59(19) . . ? C12 C11 S12 122.30(19) . . ? S11 C11 S12 115.09(14) . . ? C11 C12 S14 123.78(19) . . ? C11 C12 S13 121.18(19) . . ? S14 C12 S13 115.03(14) . . ? C14 C13 S15 127.6(2) . . ? C14 C13 S11 116.88(19) . . ? S15 C13 S11 115.46(13) . . ? C13 C14 S16 128.6(2) . . ? C13 C14 S12 117.07(19) . . ? S16 C14 S12 114.27(14) . . ? C16 C15 S13 116.87(18) . . ? C16 C15 I11 126.82(18) . . ? S13 C15 I11 116.29(12) . . ? C15 C16 S14 117.68(19) . . ? C15 C16 I12 126.35(18) . . ? S14 C16 I12 115.97(13) . . ? C18 C17 S15 112.55(18) . . ? C17 C18 S16 114.43(18) . . ? C31 S31 C33 95.35(12) . . ? C31 S32 C34 95.27(12) . . ? C35 S33 C32 95.50(12) . . ? C36 S34 C32 94.74(11) . . ? C33 S35 C37 98.64(13) . . ? C34 S36 C38 103.90(13) . . ? C32 C31 S31 122.16(19) . . ? C32 C31 S32 122.40(19) . . ? S31 C31 S32 115.42(14) . . ? C31 C32 S33 122.35(19) . . ? C31 C32 S34 122.84(19) . . ? S33 C32 S34 114.79(14) . . ? C34 C33 S35 127.6(2) . . ? C34 C33 S31 117.13(19) . . ? S35 C33 S31 115.22(14) . . ? C33 C34 S36 128.4(2) . . ? C33 C34 S32 116.83(19) . . ? S36 C34 S32 114.72(14) . . ? C36 C35 S33 116.71(19) . . ? C36 C35 I31 124.20(19) . . ? S33 C35 I31 119.07(13) . . ? C35 C36 S34 118.10(19) . . ? C35 C36 I32 126.29(18) . . ? S34 C36 I32 115.61(12) . . ? C38 C37 S35 113.9(2) . . ? C37 C38 S36 116.1(2) . . ? C2 C1 C3 124.6(3) . . ? C1 C2 C4 121.5(3) . . ? O2 C3 O1 125.2(2) . . ? O2 C3 C1 118.7(2) . . ? O1 C3 C1 116.1(3) . . ? O4 C4 O3 124.5(3) . . ? O4 C4 C2 123.4(3) . . ? O3 C4 C2 112.1(3) . . ?