# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2008

data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Xiangfeng Shao'
_publ_contact_author_email       'SHAO XF@KUCHEM.KYOTO-U.AC.JP'

_publ_section_title              
;
Formation of Two-dimensional Metals by Weak
Intermolecular Interactions Based on the Asymmetric EDO-TTF Derivatives
;
loop_
_publ_author_name
'Xiangfeng Shao'
'Alexander D. Dubrovskiy'
'Shin-ya Koshihara'
'Tsuyoshi Murata'
'Yoshiaki Nakano'
;
A.Otsuka
;
'Gunzi Saito'
'Hideki Yamochi'
'Yukihiro Yoshida'

# Attachment 'MeEDO-TTF.cif'

# Copyright The Royal Society of Chemistry, 2008
# CCDC Number: 662996

data_MeEDO-TTF
_database_code_depnum_ccdc_archive 'CCDC 662996'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4,5-ethylnenedioxy-4'methyltetrathiafulvalene
;

_chemical_name_common            4,5-ethylnenedioxy-4'methyltetrathiafulvalene
_chemical_melting_point          355.0-355.5
_chemical_formula_moiety         'C9 H8 O2 S4'
_chemical_formula_sum            'C9 H8 O2 S4'
_chemical_formula_weight         276.4

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           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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                   27.474(6)
_cell_length_b                   11.463(3)
_cell_length_c                   7.4590(14)
_cell_angle_alpha                90.000
_cell_angle_beta                 96.485(16)
_cell_angle_gamma                90.000
_cell_volume                     2334.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17
_cell_measurement_theta_min      12.3
_cell_measurement_theta_max      17.4

_exptl_crystal_description       PLATE
_exptl_crystal_colour            RED
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6490
_exptl_absorpt_correction_T_max  0.8908

_exptl_special_details           
;
the single crystals were obtaine by recrystallization from hexane.
;
_diffrn_ambient_temperature      'room temperature'
_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  'Mac Science MXC-chi'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_reflns_number            4180
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.06
_reflns_number_total             4095
_reflns_number_gt                2843
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELXL-97 (Sheldrick, 1997)'
_computing_cell_refinement       'SHELXL-97 (Sheldrick, 1997)'
_computing_data_reduction        'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Ortep-3 for Windows (Farrugia, 1997)'

_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^)+(0.0825P)^2^+4.4021P] 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_number_reflns         2842
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1701
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_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
S1A S 0.87793(7) 0.09043(15) 0.5886(2) 0.0588(5) Uani 1 1 d . . .
S2A S 0.89448(8) -0.07693(17) 0.3017(2) 0.0710(6) Uani 1 1 d . . .
S3A S 0.78873(7) 0.20701(17) 0.3282(2) 0.0627(5) Uani 1 1 d . . .
S4A S 0.80855(7) 0.04393(17) 0.0346(2) 0.0680(6) Uani 1 1 d . . .
O1A O 0.73699(19) 0.3393(4) 0.0860(6) 0.0731(14) Uani 1 1 d . . .
O2A O 0.7546(2) 0.1796(5) -0.1997(6) 0.0797(16) Uani 1 1 d . . .
C1A C 0.8604(2) 0.0426(5) 0.3678(8) 0.0501(15) Uani 1 1 d . . .
C2A C 0.8239(2) 0.0911(6) 0.2588(8) 0.0534(16) Uani 1 1 d . . .
C3A C 0.7650(2) 0.2425(6) 0.1071(9) 0.0548(16) Uani 1 1 d . . .
C4A C 0.7742(2) 0.1701(6) -0.0230(9) 0.0601(17) Uani 1 1 d . . .
C5A C 0.9290(2) -0.0019(6) 0.6273(9) 0.0595(17) Uani 1 1 d . . .
C6A C 0.9357(3) -0.0751(7) 0.4976(10) 0.072(2) Uani 1 1 d . . .
H6A H 0.9622 -0.1258 0.5099 0.087 Uiso 1 1 calc . . .
C7A C 0.7229(6) 0.3612(13) -0.0963(13) 0.177(7) Uani 1 1 d . . .
H7A1 H 0.6915 0.4006 -0.1053 0.213 Uiso 1 1 calc . . .
H7A2 H 0.7463 0.4160 -0.1367 0.213 Uiso 1 1 calc . . .
C8A C 0.7186(4) 0.2695(8) -0.2179(12) 0.095(3) Uani 1 1 d . . .
H8A1 H 0.7181 0.3022 -0.3380 0.114 Uiso 1 1 calc . . .
H8A2 H 0.6869 0.2333 -0.2115 0.114 Uiso 1 1 calc . . .
C9A C 0.9599(3) 0.0088(7) 0.8054(11) 0.081(2) Uani 1 1 d . . .
H9A1 H 0.9440 0.0596 0.8830 0.098 Uiso 1 1 calc . . .
H9A2 H 0.9913 0.0404 0.7871 0.098 Uiso 1 1 calc . . .
H9A3 H 0.9641 -0.0668 0.8602 0.098 Uiso 1 1 calc . . .
S1B S 0.90994(7) 0.58146(18) 0.4745(2) 0.0625(5) Uani 1 1 d . . .
S2B S 0.84244(6) 0.61210(18) 0.1436(2) 0.0647(5) Uani 1 1 d . . .
S3B S 1.00123(7) 0.6559(2) 0.2622(2) 0.0691(6) Uani 1 1 d . . .
S4B S 0.93220(7) 0.6906(2) -0.0720(2) 0.0698(6) Uani 1 1 d . . .
O1B O 1.07546(18) 0.6841(5) 0.0672(7) 0.0792(15) Uani 1 1 d . . .
O2B O 1.00865(17) 0.7162(4) -0.2573(6) 0.0664(13) Uani 1 1 d . . .
C1B C 0.9033(2) 0.6205(5) 0.2458(8) 0.0504(15) Uani 1 1 d . . .
C2B C 0.9403(2) 0.6526(6) 0.1564(8) 0.0498(15) Uani 1 1 d . . .
C3B C 1.0253(2) 0.6778(6) 0.0575(8) 0.0560(16) Uani 1 1 d . . .
C4B C 0.9951(2) 0.6927(6) -0.0906(8) 0.0518(15) Uani 1 1 d . . .
C5B C 0.8521(2) 0.5164(6) 0.4693(9) 0.0556(16) Uani 1 1 d . . .
C6B C 0.8221(2) 0.5319(6) 0.3185(9) 0.0589(17) Uani 1 1 d . . .
H6B H 0.7907 0.5004 0.3068 0.071 Uiso 1 1 calc . . .
C7B C 1.0899(3) 0.7005(11) -0.1025(14) 0.110(4) Uani 1 1 d . . .
H7B1 H 1.1124 0.7661 -0.0926 0.132 Uiso 1 1 calc . . .
H7B2 H 1.1091 0.6325 -0.1269 0.132 Uiso 1 1 calc . . .
C8B C 1.0588(4) 0.7190(13) -0.2518(14) 0.129(5) Uani 1 1 d . . .
H8B1 H 1.0672 0.6625 -0.3401 0.155 Uiso 1 1 calc . . .
H8B2 H 1.0669 0.7951 -0.2969 0.155 Uiso 1 1 calc . . .
C9B C 0.8402(3) 0.4526(8) 0.6339(10) 0.082(2) Uani 1 1 d . . .
H9B1 H 0.8057 0.4590 0.6435 0.099 Uiso 1 1 calc . . .
H9B2 H 0.8583 0.4861 0.7390 0.099 Uiso 1 1 calc . . .
H9B3 H 0.8488 0.3719 0.6248 0.099 Uiso 1 1 calc . . .

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
S1A 0.0626(11) 0.0606(10) 0.0511(9) -0.0073(8) -0.0027(7) 0.0066(9)
S2A 0.0789(13) 0.0667(12) 0.0639(11) -0.0165(9) -0.0079(9) 0.0219(10)
S3A 0.0626(11) 0.0737(12) 0.0503(9) -0.0113(8) -0.0006(7) 0.0164(9)
S4A 0.0744(13) 0.0708(12) 0.0553(10) -0.0180(9) -0.0085(8) 0.0161(10)
O1A 0.080(4) 0.074(3) 0.065(3) 0.001(3) 0.006(3) 0.027(3)
O2A 0.094(4) 0.098(4) 0.044(3) -0.003(3) -0.005(2) 0.025(3)
C1A 0.045(4) 0.049(4) 0.056(4) -0.004(3) 0.007(3) -0.003(3)
C2A 0.061(4) 0.052(4) 0.049(3) -0.009(3) 0.010(3) 0.001(3)
C3A 0.048(4) 0.061(4) 0.055(4) 0.003(3) 0.004(3) 0.005(3)
C4A 0.054(4) 0.072(5) 0.054(4) 0.000(3) 0.005(3) 0.000(3)
C5A 0.059(4) 0.052(4) 0.064(4) -0.001(3) -0.006(3) 0.003(3)
C6A 0.077(5) 0.064(5) 0.073(5) 0.001(4) -0.007(4) 0.021(4)
C7A 0.263(17) 0.197(13) 0.065(6) -0.005(7) -0.012(8) 0.163(13)
C8A 0.114(7) 0.083(6) 0.078(6) 0.006(5) -0.026(5) 0.009(6)
C9A 0.090(6) 0.077(5) 0.070(5) -0.004(4) -0.022(4) 0.012(5)
S1B 0.0624(11) 0.0807(12) 0.0435(9) 0.0007(8) 0.0015(7) -0.0092(9)
S2B 0.0515(10) 0.0866(13) 0.0542(10) 0.0109(9) -0.0015(7) 0.0007(9)
S3B 0.0525(10) 0.1025(15) 0.0501(9) 0.0072(9) -0.0036(7) -0.0073(10)
S4B 0.0507(10) 0.1073(16) 0.0504(9) 0.0154(10) 0.0016(7) -0.0032(10)
O1B 0.048(3) 0.110(4) 0.078(3) 0.009(3) 0.005(2) -0.002(3)
O2B 0.064(3) 0.084(3) 0.053(3) 0.003(2) 0.012(2) -0.005(3)
C1B 0.056(4) 0.048(4) 0.047(3) -0.005(3) 0.004(3) 0.000(3)
C2B 0.045(4) 0.053(4) 0.051(3) -0.002(3) 0.003(3) -0.005(3)
C3B 0.055(4) 0.063(4) 0.050(4) 0.001(3) 0.007(3) -0.001(3)
C4B 0.047(4) 0.056(4) 0.053(4) -0.003(3) 0.007(3) -0.003(3)
C5B 0.060(4) 0.054(4) 0.054(4) -0.003(3) 0.013(3) -0.002(3)
C6B 0.049(4) 0.064(4) 0.066(4) 0.001(3) 0.012(3) -0.001(3)
C7B 0.061(5) 0.178(11) 0.095(7) 0.001(7) 0.028(5) -0.006(6)
C8B 0.063(6) 0.241(15) 0.088(7) 0.029(8) 0.022(5) 0.004(8)
C9B 0.099(6) 0.086(6) 0.063(5) 0.007(4) 0.014(4) -0.010(5)

_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
S1A C1A 1.751(6) . y
S1A C5A 1.755(7) . y
S2A C6A 1.745(8) . y
S2A C1A 1.761(6) . y
S3A C3A 1.751(6) . y
S3A C2A 1.755(6) . y
S4A C4A 1.753(7) . y
S4A C2A 1.763(6) . y
O1A C3A 1.350(8) . n
O1A C7A 1.394(10) . n
O2A C4A 1.371(8) . n
O2A C8A 1.425(10) . n
C1A C2A 1.340(9) . y
C3A C4A 1.323(9) . y
C5A C6A 1.309(10) . y
C5A C9A 1.498(10) . n
C7A C8A 1.385(15) . n
S1B C5B 1.751(7) . y
S1B C1B 1.753(6) . y
S2B C6B 1.739(7) . y
S2B C1B 1.761(6) . y
S3B C3B 1.749(7) . y
S3B C2B 1.769(6) . y
S4B C2B 1.748(6) . y
S4B C4B 1.751(6) . y
O1B C3B 1.374(8) . n
O1B C7B 1.381(10) . n
O2B C4B 1.364(7) . n
O2B C8B 1.373(10) . n
C1B C2B 1.328(9) . y
C3B C4B 1.315(9) . y
C5B C6B 1.329(9) . y
C5B C9B 1.497(10) . n
C7B C8B 1.342(13) . n

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
C1A S1A C5A 95.4(3) . . n
C6A S2A C1A 94.0(3) . . n
C3A S3A C2A 93.2(3) . . n
C4A S4A C2A 92.5(3) . . n
C3A O1A C7A 110.7(6) . . n
C4A O2A C8A 110.1(6) . . n
C2A C1A S1A 123.2(5) . . n
C2A C1A S2A 122.6(5) . . n
S1A C1A S2A 114.2(4) . . n
C1A C2A S3A 122.4(5) . . n
C1A C2A S4A 122.0(5) . . n
S3A C2A S4A 115.6(4) . . n
C4A C3A O1A 125.7(6) . . n
C4A C3A S3A 117.6(5) . . n
O1A C3A S3A 116.6(5) . . n
C3A C4A O2A 124.6(7) . . n
C3A C4A S4A 118.7(5) . . n
O2A C4A S4A 116.3(5) . . n
C6A C5A C9A 126.5(7) . . n
C6A C5A S1A 116.2(5) . . n
C9A C5A S1A 117.3(5) . . n
C5A C6A S2A 119.7(6) . . n
C8A C7A O1A 119.7(10) . . n
C7A C8A O2A 118.6(8) . . n
C5B S1B C1B 95.3(3) . . n
C6B S2B C1B 94.2(3) . . n
C3B S3B C2B 92.6(3) . . n
C2B S4B C4B 93.6(3) . . n
C3B O1B C7B 110.5(6) . . n
C4B O2B C8B 110.6(6) . . n
C2B C1B S1B 123.9(5) . . n
C2B C1B S2B 122.7(5) . . n
S1B C1B S2B 113.4(4) . . n
C1B C2B S4B 122.5(5) . . n
C1B C2B S3B 121.4(5) . . n
S4B C2B S3B 116.1(3) . . n
C4B C3B O1B 124.7(6) . . n
C4B C3B S3B 119.2(5) . . n
O1B C3B S3B 116.0(5) . . n
C3B C4B O2B 125.6(6) . . n
C3B C4B S4B 117.7(5) . . n
O2B C4B S4B 116.6(4) . . n
C6B C5B C9B 125.9(7) . . n
C6B C5B S1B 115.9(5) . . n
C9B C5B S1B 118.2(5) . . n
C5B C6B S2B 119.0(5) . . n
C8B C7B O1B 124.0(8) . . n
C7B C8B O2B 124.4(8) . . n

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.094

# Attachment 'MeSEDO-TTF.cif'

# Copyright The Royal Society of Chemistry, 2008
# CCDC Number: 662997

data_MeSEDO-TTF
_database_code_depnum_ccdc_archive 'CCDC 662997'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4,5-ethylenedioxy-4'-methylthiotetrathiafulvalene'
;
_chemical_name_common            
4,5-ethylenedioxy-4'-methylthiotetrathiafulvalene'
_chemical_melting_point          337.5-337.7
_chemical_formula_moiety         'C9 H8 O2 S5'
_chemical_formula_sum            'C9 H8 O2 S5'
_chemical_formula_weight         308.45

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           Orthorhombic
_symmetry_space_group_name_H-M   P_b_c_a

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

_cell_length_a                   13.6810(10)
_cell_length_b                   17.4380(13)
_cell_length_c                   10.5300(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2512.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    19
_cell_measurement_theta_min      3
_cell_measurement_theta_max      35

_exptl_crystal_description       red
_exptl_crystal_colour            plate
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
The single crystals were obtained by recrystallization
from hexane/cyclo-hexane.
;

_diffrn_ambient_temperature      293(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  'Mac Science MXC-chi'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_reflns_number            2569
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         26.44
_reflns_number_total             2569
_reflns_number_gt                1661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELXL-97 (Sheldrick, 1997)'
_computing_cell_refinement       'SHELXL-97 (Sheldrick, 1997)'
_computing_data_reduction        'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 2004'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for windows (Farrugia,1997)'
_computing_publication_material  'Ortep-3 for windows (Farrugia,1997)'

_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^)+(0.0631P)^2^+1.4865P] 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_number_reflns         2569
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
S3 S 0.55051(7) 0.16291(8) 0.35320(9) 0.0811(4) Uani 1 1 d . . .
S1 S 0.35162(7) 0.08077(8) 0.44606(9) 0.0795(4) Uani 1 1 d . . .
S4 S 0.63444(8) 0.14193(9) 0.61127(10) 0.0913(4) Uani 1 1 d . . .
S2 S 0.43595(8) 0.05749(7) 0.70068(9) 0.0788(3) Uani 1 1 d . . .
S5 S 0.15538(8) 0.01826(7) 0.52383(12) 0.0828(4) Uani 1 1 d . . .
O1 O 0.7247(2) 0.20773(16) 0.2715(2) 0.0755(7) Uani 1 1 d . . .
O2 O 0.8064(2) 0.18847(17) 0.5220(3) 0.0806(8) Uani 1 1 d . . .
C2 C 0.5363(3) 0.1263(2) 0.5085(3) 0.0638(9) Uani 1 1 d . . .
C1 C 0.4531(3) 0.0922(2) 0.5460(3) 0.0628(9) Uani 1 1 d . . .
C3 C 0.6742(3) 0.1829(2) 0.3757(3) 0.0604(9) Uani 1 1 d . . .
C5 C 0.2747(3) 0.0433(2) 0.5642(4) 0.0636(9) Uani 1 1 d . . .
C4 C 0.7113(3) 0.1746(2) 0.4901(3) 0.0657(9) Uani 1 1 d . . .
C6 C 0.3143(3) 0.0336(2) 0.6775(4) 0.0705(10) Uani 1 1 d . . .
H6 H 0.2773 0.0142 0.7442 0.085 Uiso 1 1 calc . . .
C7 C 0.8136(3) 0.2428(3) 0.3111(4) 0.0872(12) Uani 1 1 d . . .
H7A H 0.7995 0.2938 0.3432 0.105 Uiso 1 1 calc . . .
H7B H 0.8563 0.2484 0.2382 0.105 Uiso 1 1 calc . . .
C8 C 0.8640(3) 0.1996(3) 0.4085(5) 0.0911(13) Uani 1 1 d . . .
H8B H 0.8819 0.1499 0.3744 0.109 Uiso 1 1 calc . . .
H8A H 0.9238 0.2262 0.4308 0.109 Uiso 1 1 calc . . .
C9 C 0.1000(3) 0.1106(3) 0.5037(5) 0.0952(14) Uani 1 1 d . . .
H92 H 0.1370 0.1483 0.5496 0.114 Uiso 1 1 calc . . .
H91 H 0.0343 0.1093 0.5357 0.114 Uiso 1 1 calc . . .
H93 H 0.0990 0.1236 0.4152 0.114 Uiso 1 1 calc . . .

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
S3 0.0585(6) 0.1272(9) 0.0576(6) 0.0164(5) -0.0100(4) -0.0134(6)
S1 0.0591(6) 0.1257(9) 0.0537(5) 0.0020(5) -0.0024(4) -0.0187(6)
S4 0.0732(7) 0.1469(11) 0.0538(6) 0.0143(6) -0.0118(5) -0.0319(7)
S2 0.0682(6) 0.1090(8) 0.0592(6) 0.0157(5) -0.0048(5) -0.0037(6)
S5 0.0623(6) 0.0929(8) 0.0932(8) -0.0030(6) 0.0008(5) -0.0188(5)
O1 0.0633(16) 0.1006(19) 0.0626(15) 0.0115(14) 0.0038(12) -0.0036(14)
O2 0.0578(16) 0.114(2) 0.0700(16) 0.0034(16) -0.0108(13) -0.0090(14)
C2 0.057(2) 0.080(2) 0.0552(19) 0.0029(17) -0.0037(16) -0.0053(17)
C1 0.060(2) 0.076(2) 0.0525(18) -0.0016(17) -0.0046(16) 0.0003(17)
C3 0.052(2) 0.071(2) 0.059(2) 0.0013(17) 0.0010(15) 0.0023(16)
C5 0.055(2) 0.069(2) 0.067(2) -0.0018(18) 0.0048(17) -0.0038(16)
C4 0.054(2) 0.081(2) 0.062(2) 0.0019(18) -0.0046(16) -0.0024(17)
C6 0.067(2) 0.080(2) 0.065(2) 0.0139(19) 0.0089(18) 0.0016(19)
C7 0.066(3) 0.106(3) 0.090(3) 0.003(3) 0.005(2) -0.012(2)
C8 0.060(3) 0.116(4) 0.097(3) 0.021(3) 0.002(2) -0.005(2)
C9 0.059(3) 0.122(4) 0.105(4) 0.015(3) -0.011(2) 0.000(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
S3 C3 1.745(4) . y
S3 C2 1.767(4) . y
S1 C5 1.755(4) . y
S1 C1 1.756(4) . y
S4 C2 1.746(4) . y
S4 C4 1.748(4) . y
S2 C6 1.733(5) . y
S2 C1 1.755(4) . y
S5 C5 1.744(4) . n
S5 C9 1.790(6) . n
O1 C3 1.366(5) . n
O1 C7 1.425(6) . n
O2 C4 1.366(5) . n
O2 C8 1.444(6) . n
C2 C1 1.339(6) . y
C3 C4 1.313(6) . y
C5 C6 1.319(6) . y
C7 C8 1.444(7) . y

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 S3 C2 93.0(2) . . n
C5 S1 C1 95.4(2) . . n
C2 S4 C4 93.4(2) . . n
C6 S2 C1 94.7(2) . . n
C5 S5 C9 101.7(2) . . n
C3 O1 C7 109.6(3) . . n
C4 O2 C8 109.8(4) . . n
C1 C2 S4 122.6(3) . . n
C1 C2 S3 121.7(3) . . n
S4 C2 S3 115.6(2) . . n
C2 C1 S2 122.7(3) . . n
C2 C1 S1 123.1(3) . . n
S2 C1 S1 114.1(2) . . n
C4 C3 O1 125.2(4) . . n
C4 C3 S3 118.4(3) . . n
O1 C3 S3 116.4(3) . . n
C6 C5 S5 124.9(4) . . n
C6 C5 S1 116.2(3) . . n
S5 C5 S1 118.8(3) . . n
C3 C4 O2 125.0(4) . . n
C3 C4 S4 118.3(3) . . n
O2 C4 S4 116.7(3) . . n
C5 C6 S2 119.4(3) . . n
O1 C7 C8 113.0(5) . . n
O2 C8 C7 113.6(4) . . n

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.062


# Attachment '(MeEDO-TTF)2BF4.cif'

data_(MeEDO-TTF)2BF4
_database_code_depnum_ccdc_archive 'CCDC 662998'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis-4,5-ethylenedioxy-4'-methyltetrathiafulvalene-tetrafluoroborate
;
_chemical_name_common            
;bis-4,5-ethylenedioxy-4'-methyltetrathiafulvalene-
tetrafluoroborate
;
_chemical_melting_point          423(decompose)
_chemical_formula_moiety         'C9 H8 B0.5 F2 O2 S4'
_chemical_formula_sum            'C18 H16 B F4 O4 S8'
_chemical_formula_weight         639.66

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   Cmcm

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

_cell_length_a                   28.7520(17)
_cell_length_b                   12.3690(12)
_cell_length_c                   6.9690(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2478.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    'room temperature'

_exptl_crystal_description       'elongated plate'
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      no
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1300
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
The crystals were obtained by electrocrystallization of MeEDO-TTF
in the presence of TBA.BF4 in EtOH by applying constant current.
For the structure refinement, the positional parameters of hydrogen
atoms of vinyl and methyl hrdrogen atoms were obtained by
differential synthesis and refined with isotropic temperature
factors. To express the disorder by the combination of tetrahedrons
having different orientations, the SADI instruction was used
for the bond lengths of the anion B-F (SADI B F1 B F2 B F3 B F4)
and the distances between the fluorine atoms (SADI F2 F4 F1 F3).
;

_diffrn_ambient_temperature      'room temperature'
_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  'Macscience DIP-2020K'
_diffrn_measurement_method       'flat imagine plate'
_diffrn_detector_area_resol_mean 12.5
_diffrn_reflns_number            1351
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         26.08
_reflns_number_total             1351
_reflns_number_gt                1010
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELX97 (Sheldrick, 1997)'
_computing_cell_refinement       'SHELX97 (Sheldrick, 1997)'
_computing_data_reduction        'SHELX97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 2004'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Ortep-3 for Windows (Farrugia, 1997)'

_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^)+(0.1304P)^2^+0.5208P] 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_number_reflns         1351
_refine_ls_number_parameters     136
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.056
_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
H6 H 0.083(2) 0.682(5) 0.2500 0.084(18) Uiso 1 2 d S . .
H92 H 0.045(2) 0.501(6) 0.2500 0.095(19) Uiso 1 2 d S . .
H91 H 0.070(2) 0.410(6) 0.379(9) 0.17(3) Uiso 1 1 d . . .
S1 S 0.16998(4) 0.46016(9) 0.2500 0.0532(4) Uani 1 2 d S . .
S2 S 0.16793(4) 0.69708(10) 0.2500 0.0607(5) Uani 1 2 d S . .
S3 S 0.28345(4) 0.46802(8) 0.2500 0.0525(4) Uani 1 2 d S . .
S4 S 0.27785(4) 0.70755(9) 0.2500 0.0585(4) Uani 1 2 d S . .
O1 O 0.37562(11) 0.4832(3) 0.2500 0.0641(9) Uani 1 2 d S . .
O2 O 0.37006(11) 0.7171(3) 0.2500 0.0664(10) Uani 1 2 d S . .
C1 C 0.20183(17) 0.5798(3) 0.2500 0.0509(10) Uani 1 2 d S . .
C2 C 0.24875(16) 0.5840(3) 0.2500 0.0481(10) Uani 1 2 d S . .
C3 C 0.33545(16) 0.5420(4) 0.2500 0.0551(11) Uani 1 2 d S . .
C4 C 0.33246(15) 0.6486(4) 0.2500 0.0557(11) Uani 1 2 d S . .
C5 C 0.11558(16) 0.5225(4) 0.2500 0.0608(12) Uani 1 2 d S . .
C6 C 0.11509(17) 0.6292(4) 0.2500 0.0640(13) Uani 1 2 d S . .
C7 C 0.4145(2) 0.5543(5) 0.2989(17) 0.074(4) Uani 0.50 1 d P . .
C8 C 0.4109(2) 0.6576(6) 0.3131(14) 0.086(4) Uani 0.50 1 d P . .
C9 C 0.0726(2) 0.4511(5) 0.2500 0.0755(16) Uani 1 2 d S . .
B B 0.5000 0.2846(9) 0.2500 0.149(8) Uani 1 4 d SD . .
F1 F 0.5416(3) 0.3194(8) 0.2500 0.131(6) Uani 0.50 2 d SPD . .
F2 F 0.5000 0.2161(14) 0.400(3) 0.293(12) Uani 0.50 2 d SPD . .
F3 F 0.5205(7) 0.3429(19) 0.376(3) 0.274(18) Uani 0.25 1 d PD . .
F4 F 0.5000 0.1815(11) 0.2500 0.43(4) Uani 0.50 4 d SPD . .

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 0.0486(7) 0.0409(6) 0.0700(8) 0.000 0.000 0.0001(4)
S2 0.0543(7) 0.0417(7) 0.0860(10) 0.000 0.000 0.0052(4)
S3 0.0529(6) 0.0373(6) 0.0672(8) 0.000 0.000 0.0023(4)
S4 0.0489(7) 0.0374(7) 0.0890(10) 0.000 0.000 0.0010(4)
O1 0.0501(17) 0.0495(18) 0.093(3) 0.000 0.000 0.0082(14)
O2 0.0512(17) 0.0446(17) 0.103(3) 0.000 0.000 -0.0047(14)
C1 0.053(2) 0.044(2) 0.056(3) 0.000 0.000 0.0053(17)
C2 0.047(2) 0.035(2) 0.062(3) 0.000 0.000 0.0031(15)
C3 0.053(2) 0.046(2) 0.066(3) 0.000 0.000 0.0061(19)
C4 0.048(2) 0.048(2) 0.071(3) 0.000 0.000 -0.0044(18)
C5 0.051(2) 0.056(3) 0.076(3) 0.000 0.000 0.001(2)
C6 0.051(2) 0.053(3) 0.088(4) 0.000 0.000 0.006(2)
C7 0.045(3) 0.059(3) 0.117(14) 0.002(4) -0.010(4) -0.001(3)
C8 0.049(3) 0.065(4) 0.144(13) -0.004(4) -0.019(4) 0.002(3)
C9 0.049(3) 0.071(3) 0.106(5) 0.000 0.000 -0.005(3)
B 0.060(7) 0.075(8) 0.31(3) 0.000 0.000 0.000
F1 0.048(4) 0.055(4) 0.291(19) 0.000 0.000 0.002(3)
F2 0.221(17) 0.26(2) 0.40(3) 0.24(2) 0.000 0.000
F3 0.25(3) 0.24(2) 0.33(3) 0.06(2) -0.18(3) -0.17(2)
F4 0.046(7) 0.056(8) 1.19(12) 0.000 0.000 0.000

_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 1.740(4) . y
S1 C5 1.744(5) . y
S2 C6 1.736(5) . y
S2 C1 1.748(4) . y
S3 C2 1.747(4) . y
S3 C3 1.753(5) . y
S4 C4 1.731(4) . y
S4 C2 1.742(4) . y
O1 C3 1.365(5) . n
O1 C7 1.464(7) . n
O1 C7 1.464(7) 10_556 n
O2 C4 1.374(5) . n
O2 C8 1.453(8) . n
O2 C8 1.453(8) 10_556 n
C1 C2 1.350(7) . y
C3 C4 1.321(7) . y
C5 C6 1.320(7) . y
C5 C9 1.518(7) . n
C7 C7 0.68(2) 10_556 n
C7 C8 1.286(9) . n
C7 C8 1.501(11) 10_556 n
C8 C8 0.880(19) 10_556 n
C8 C7 1.501(11) 10_556 n
B F1 1.272(9) . n
B F1 1.272(9) 11_655 n
B F4 1.275(14) . n
B F3 1.282(14) . n
B F3 1.282(14) 11_655 n
B F3 1.282(14) 4_655 n
B F3 1.282(14) 10_556 n
B F2 1.346(13) 10_556 n
B F2 1.346(13) . n
F1 F3 1.11(2) 10_556 n
F1 F3 1.11(2) . n
F2 F4 1.13(3) . n
F2 F3 1.68(3) . n
F2 F3 1.68(3) 11_655 n
F3 F3 1.18(4) 11_655 n
F3 F3 1.76(5) 10_556 n
F4 F2 1.13(3) 10_556 n

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 C5 95.5(2) . . n
C6 S2 C1 95.0(2) . . n
C2 S3 C3 93.3(2) . . n
C4 S4 C2 93.8(2) . . n
C3 O1 C7 109.1(4) . . n
C3 O1 C7 109.1(4) . 10_556 n
C7 O1 C7 26.9(9) . 10_556 n
C4 O2 C8 108.9(4) . . n
C4 O2 C8 108.9(4) . 10_556 n
C8 O2 C8 35.2(8) . 10_556 n
C2 C1 S1 124.0(3) . . n
C2 C1 S2 121.7(3) . . n
S1 C1 S2 114.4(3) . . n
C1 C2 S4 120.9(3) . . n
C1 C2 S3 122.6(3) . . n
S4 C2 S3 116.5(3) . . n
C4 C3 O1 125.9(4) . . n
C4 C3 S3 117.7(3) . . n
O1 C3 S3 116.4(3) . . n
C3 C4 O2 124.4(4) . . n
C3 C4 S4 118.7(3) . . n
O2 C4 S4 117.0(3) . . n
C6 C5 C9 125.0(5) . . n
C6 C5 S1 116.9(4) . . n
C9 C5 S1 118.1(4) . . n
C5 C6 S2 118.3(4) . . n
C7 C7 C8 94.4(7) 10_556 . n
C7 C7 O1 76.5(5) 10_556 . n
C8 C7 O1 123.6(6) . . n
C7 C7 C8 58.7(5) 10_556 10_556 n
C8 C7 C8 35.7(8) . 10_556 n
O1 C7 C8 109.7(7) . 10_556 n
C8 C8 C7 85.6(7) 10_556 . n
C8 C8 O2 72.4(4) 10_556 . n
C7 C8 O2 123.0(7) . . n
C8 C8 C7 58.7(5) 10_556 10_556 n
C7 C8 C7 26.9(9) . 10_556 n
O2 C8 C7 109.2(6) . 10_556 n
F1 B F1 140.5(12) . 11_655 n
F1 B F4 109.8(6) . . n
F1 B F4 109.8(6) 11_655 . n
F1 B F3 51.5(10) . . n
F1 B F3 104.0(12) 11_655 . n
F4 B F3 124.2(13) . . n
F1 B F3 104.0(12) . 11_655 n
F1 B F3 51.5(10) 11_655 11_655 n
F4 B F3 124.2(13) . 11_655 n
F3 B F3 55(2) . 11_655 n
F1 B F3 104.0(12) . 4_655 n
F1 B F3 51.5(10) 11_655 4_655 n
F4 B F3 124.2(13) . 4_655 n
F3 B F3 112(3) . 4_655 n
F3 B F3 87(2) 11_655 4_655 n
F1 B F3 51.5(10) . 10_556 n
F1 B F3 104.0(12) 11_655 10_556 n
F4 B F3 124.2(13) . 10_556 n
F3 B F3 87(2) . 10_556 n
F3 B F3 112(3) 11_655 10_556 n
F3 B F3 55(2) 4_655 10_556 n
F1 B F2 102.3(4) . 10_556 n
F1 B F2 102.3(4) 11_655 10_556 n
F4 B F2 51.0(11) . 10_556 n
F3 B F2 152.6(10) . 10_556 n
F3 B F2 152.6(10) 11_655 10_556 n
F3 B F2 79.6(16) 4_655 10_556 n
F3 B F2 79.6(16) 10_556 10_556 n
F1 B F2 102.3(4) . . n
F1 B F2 102.3(4) 11_655 . n
F4 B F2 51.0(11) . . n
F3 B F2 79.6(16) . . n
F3 B F2 79.6(16) 11_655 . n
F3 B F2 152.6(10) 4_655 . n
F3 B F2 152.6(10) 10_556 . n
F2 B F2 102(2) 10_556 . n
F3 F1 F3 105(3) 10_556 . n
F3 F1 B 64.7(8) 10_556 . n
F3 F1 B 64.7(8) . . n
F4 F2 B 61.2(9) . . n
F4 F2 F3 105.2(11) . . n
B F2 F3 48.5(9) . . n
F4 F2 F3 105.2(11) . 11_655 n
B F2 F3 48.5(9) . 11_655 n
F3 F2 F3 41.0(15) . 11_655 n
F1 F3 F3 123.2(9) . 11_655 n
F1 F3 B 63.8(10) . . n
F3 F3 B 62.6(11) 11_655 . n
F1 F3 F2 91.5(15) . . n
F3 F3 F2 69.5(7) 11_655 . n
B F3 F2 51.9(9) . . n
F1 F3 F3 37.4(13) . 10_556 n
F3 F3 F3 90.000(2) 11_655 10_556 n
B F3 F3 46.6(12) . 10_556 n
F2 F3 F3 95.7(7) . 10_556 n
F2 F4 F2 135.5(19) . 10_556 n
F2 F4 B 67.7(9) . . n
F2 F4 B 67.7(9) 10_556 . n

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.08
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.089

# Attachment '(MeEDO-TTF)2ClO4.cif'

data_(MeEDO-TTF)2ClO4
_database_code_depnum_ccdc_archive 'CCDC 662999'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis-4,5-ethylenedioxy-4'-methyltetrathiafulvalene-perchlorate
;
_chemical_name_common            
bis-4,5-ethylenedioxy-4'-methyltetrathiafulvalene-perchlorate
_chemical_melting_point          '453 (decompose)'
_chemical_formula_moiety         'C18 H16 Cl O8 S8'
_chemical_formula_sum            'C18 H16 Cl O8 S8'
_chemical_formula_weight         652.24

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'
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           Orthorhombic
_symmetry_space_group_name_H-M   Cmcm

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

_cell_length_a                   29.107(3)
_cell_length_b                   12.4120(6)
_cell_length_c                   6.9620(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2515.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    'room temperature'

_exptl_crystal_description       'IRREGULAR PLATE'
_exptl_crystal_colour            BLACK
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1332
_exptl_absorpt_coefficient_mu    0.86
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
The crystals were obtained by electrocrystallization of MeEDO-TTF
in the presence of TBA.ClO4 in EtOH by applying constant current.
For the structure refinement, the positional parameters of hydrogen
atoms of vinyl and methyl hrdrogen atoms were obtained by
differential synthesis and refined withisotropic temperature factors.
To express the disorder by the combination of tetrahedrons having
different orientations, the SADI instruction was used for the
bond lengths of the anion Cl-O (SADI Cl O1 Cl O2 Cl O3 Cl O4)
and the distances between the chlorine atoms (SADI O2 O4 O1 O3).
;

_diffrn_ambient_temperature      'room temperature'
_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  'Mac Science DIP-2020K'
_diffrn_measurement_method       'flat imagine plate'
_diffrn_detector_area_resol_mean 12.5
_diffrn_reflns_number            1408
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         26.24
_reflns_number_total             1408
_reflns_number_gt                1073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SHELX97 (Sheldrick, 1997)'
_computing_cell_refinement       'SHELX97 (Sheldrick, 1997)'
_computing_data_reduction        'SHELX97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 2004'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Ortep-3 for Windows (Farrugia, 1997)'

_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^)+(0.1084P)^2^+1.5234P] 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_number_reflns         1408
_refine_ls_number_parameters     136
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.070
_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
H6 H 0.0827(19) 0.677(5) 0.2500 0.082(18) Uiso 1 2 d S . .
H92 H 0.050(2) 0.498(6) 0.2500 0.082(18) Uiso 1 2 d S . .
H91 H 0.0772(17) 0.403(4) 0.376(7) 0.108(16) Uiso 1 1 d . . .
S1 S 0.17113(4) 0.45899(8) 0.2500 0.0493(4) Uani 1 2 d S . .
S2 S 0.16895(4) 0.69512(9) 0.2500 0.0570(4) Uani 1 2 d S . .
S3 S 0.28335(4) 0.46763(8) 0.2500 0.0481(4) Uani 1 2 d S . .
S4 S 0.27738(4) 0.70624(9) 0.2500 0.0544(4) Uani 1 2 d S . .
O1 O 0.37440(11) 0.4838(3) 0.2500 0.0607(9) Uani 1 2 d S . .
O2 O 0.36836(11) 0.7167(3) 0.2500 0.0632(9) Uani 1 2 d S . .
C1 C 0.20205(16) 0.5787(3) 0.2500 0.0458(10) Uani 1 2 d S . .
C2 C 0.24894(16) 0.5827(3) 0.2500 0.0442(9) Uani 1 2 d S . .
C3 C 0.33443(15) 0.5410(4) 0.2500 0.0497(10) Uani 1 2 d S . .
C4 C 0.33153(14) 0.6485(4) 0.2500 0.0505(11) Uani 1 2 d S . .
C5 C 0.11716(16) 0.5200(4) 0.2500 0.0568(11) Uani 1 2 d S . .
C6 C 0.11652(18) 0.6279(4) 0.2500 0.0636(13) Uani 1 2 d S . .
C7 C 0.4134(2) 0.5561(6) 0.288(7) 0.090(12) Uani 0.50 1 d P . .
C8 C 0.4091(2) 0.6572(6) 0.3201(13) 0.077(3) Uani 0.50 1 d P . .
C9 C 0.0747(2) 0.4496(5) 0.2500 0.0694(14) Uani 1 2 d S . .
Cl Cl 0.5000 0.2841(2) 0.2500 0.1294(15) Uani 1 4 d SD . .
O11 O 0.5431(3) 0.3179(9) 0.2500 0.129(7) Uani 0.50 2 d SPD . .
O21 O 0.5000 0.2087(15) 0.401(3) 0.248(12) Uani 0.50 2 d SPD . .
O31 O 0.5221(8) 0.342(2) 0.380(4) 0.29(2) Uani 0.25 1 d PD . .
O41 O 0.5000 0.1766(11) 0.2500 0.40(4) Uani 0.50 4 d SPD . .

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 0.0464(6) 0.0415(6) 0.0600(7) 0.000 0.000 -0.0008(4)
S2 0.0518(7) 0.0410(6) 0.0782(9) 0.000 0.000 0.0046(4)
S3 0.0505(6) 0.0362(6) 0.0576(7) 0.000 0.000 0.0016(4)
S4 0.0455(7) 0.0368(6) 0.0809(10) 0.000 0.000 0.0015(4)
O1 0.0464(17) 0.0496(17) 0.086(2) 0.000 0.000 0.0076(13)
O2 0.0481(18) 0.0451(16) 0.097(3) 0.000 0.000 -0.0040(13)
C1 0.049(2) 0.038(2) 0.050(2) 0.000 0.000 0.0020(15)
C2 0.046(2) 0.0365(19) 0.050(2) 0.000 0.000 0.0022(15)
C3 0.048(2) 0.046(2) 0.056(3) 0.000 0.000 0.0092(17)
C4 0.044(2) 0.045(2) 0.062(3) 0.000 0.000 -0.0028(17)
C5 0.047(2) 0.057(3) 0.067(3) 0.000 0.000 -0.003(2)
C6 0.053(3) 0.056(3) 0.082(4) 0.000 0.000 0.009(2)
C7 0.052(3) 0.060(3) 0.16(4) 0.010(7) -0.012(8) -0.004(3)
C8 0.045(3) 0.059(3) 0.127(10) -0.002(4) -0.016(4) 0.002(3)
C9 0.047(3) 0.070(3) 0.092(4) 0.000 0.000 -0.006(2)
Cl 0.0494(12) 0.0836(15) 0.255(5) 0.000 0.000 0.000
O11 0.046(4) 0.056(5) 0.29(2) 0.000 0.000 0.000(4)
O21 0.22(2) 0.227(19) 0.29(2) 0.193(19) 0.000 0.000
O31 0.32(4) 0.28(3) 0.27(3) 0.06(2) -0.18(3) -0.25(3)
O41 0.045(8) 0.046(7) 1.10(13) 0.000 0.000 0.000

_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 1.737(4) . y
S1 C5 1.744(5) . y
S2 C1 1.737(4) . y
S2 C6 1.740(5) . y
S3 C3 1.743(5) . y
S3 C2 1.744(4) . y
S4 C4 1.732(4) . y
S4 C2 1.743(4) . y
O1 C3 1.363(5) . n
O1 C7 1.470(12) . n
O1 C7 1.470(12) 10_556 n
O2 C4 1.366(5) . n
O2 C8 1.480(7) . n
O2 C8 1.480(7) 10_556 n
C1 C2 1.366(7) . y
C3 C4 1.337(6) . y
C5 C6 1.339(7) . y
C5 C9 1.512(7) . n
C7 C7 0.53(10) 10_556 n
C7 C8 1.281(13) . n
C7 C8 1.47(3) 10_556 n
C8 C8 0.976(18) 10_556 n
C8 C7 1.47(3) 10_556 n
Cl O11 1.322(10) 11_655 n
Cl O11 1.322(10) . n
Cl O31 1.325(13) . n
Cl O31 1.325(13) 11_655 n
Cl O31 1.325(13) 4_655 n
Cl O31 1.325(13) 10_556 n
Cl O41 1.334(13) . n
Cl O21 1.410(12) 10_556 n
Cl O21 1.410(12) . n
O11 O31 1.13(3) 10_556 n
O11 O31 1.13(3) . n
O21 O41 1.13(3) . n
O21 O31 1.78(3) . n
O21 O31 1.78(3) 11_655 n
O31 O31 1.29(4) 11_655 n
O31 O31 1.81(5) 10_556 n
O41 O21 1.13(3) 10_556 n

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 C5 95.5(2) . . n
C1 S2 C6 95.0(2) . . n
C3 S3 C2 93.6(2) . . n
C4 S4 C2 93.9(2) . . n
C3 O1 C7 109.9(4) . . n
C3 O1 C7 109.9(4) . 10_556 n
C7 O1 C7 21(4) . 10_556 n
C4 O2 C8 108.6(4) . . n
C4 O2 C8 108.6(4) . 10_556 n
C8 O2 C8 38.5(7) . 10_556 n
C2 C1 S2 121.6(3) . . n
C2 C1 S1 123.3(3) . . n
S2 C1 S1 115.1(3) . . n
C1 C2 S4 120.4(3) . . n
C1 C2 S3 123.0(3) . . n
S4 C2 S3 116.6(3) . . n
C4 C3 O1 125.0(4) . . n
C4 C3 S3 117.9(3) . . n
O1 C3 S3 117.1(3) . . n
C3 C4 O2 124.7(4) . . n
C3 C4 S4 118.1(3) . . n
O2 C4 S4 117.2(3) . . n
C6 C5 C9 124.5(5) . . n
C6 C5 S1 116.5(4) . . n
C9 C5 S1 119.0(4) . . n
C5 C6 S2 117.9(4) . . n
C7 C7 C8 100(2) 10_556 . n
C7 C7 C8 59.2(17) 10_556 10_556 n
C8 C7 C8 40.9(9) . 10_556 n
C7 C7 O1 79.7(19) 10_556 . n
C8 C7 O1 123.7(6) . . n
C8 C7 O1 111(2) 10_556 . n
C8 C8 C7 80(2) 10_556 . n
C8 C8 C7 59.2(17) 10_556 10_556 n
C7 C8 C7 21(4) . 10_556 n
C8 C8 O2 70.7(3) 10_556 . n
C7 C8 O2 120.6(12) . . n
C7 C8 O2 109.1(11) 10_556 . n
O11 Cl O11 143.0(9) 11_655 . n
O11 Cl O31 106.7(12) 11_655 . n
O11 Cl O31 50.7(11) . . n
O11 Cl O31 50.7(11) 11_655 11_655 n
O11 Cl O31 106.7(12) . 11_655 n
O31 Cl O31 58(2) . 11_655 n
O11 Cl O31 50.7(11) 11_655 4_655 n
O11 Cl O31 106.7(12) . 4_655 n
O31 Cl O31 114(3) . 4_655 n
O31 Cl O31 86(2) 11_655 4_655 n
O11 Cl O31 106.7(12) 11_655 10_556 n
O11 Cl O31 50.7(11) . 10_556 n
O31 Cl O31 86(2) . 10_556 n
O31 Cl O31 114(3) 11_655 10_556 n
O31 Cl O31 58(2) 4_655 10_556 n
O11 Cl O41 108.5(5) 11_655 . n
O11 Cl O41 108.5(5) . . n
O31 Cl O41 123.0(14) . . n
O31 Cl O41 123.0(14) 11_655 . n
O31 Cl O41 123.0(14) 4_655 . n
O31 Cl O41 123.0(14) 10_556 . n
O11 Cl O21 102.2(4) 11_655 10_556 n
O11 Cl O21 102.2(4) . 10_556 n
O31 Cl O21 150.8(13) . 10_556 n
O31 Cl O21 150.8(13) 11_655 10_556 n
O31 Cl O21 81.4(17) 4_655 10_556 n
O31 Cl O21 81.4(17) 10_556 10_556 n
O41 Cl O21 48.4(11) . 10_556 n
O11 Cl O21 102.2(4) 11_655 . n
O11 Cl O21 102.2(4) . . n
O31 Cl O21 81.4(17) . . n
O31 Cl O21 81.4(17) 11_655 . n
O31 Cl O21 150.8(13) 4_655 . n
O31 Cl O21 150.8(13) 10_556 . n
O41 Cl O21 48.4(11) . . n
O21 Cl O21 97(2) 10_556 . n
O31 O11 O31 106(3) 10_556 . n
O31 O11 Cl 64.8(8) 10_556 . n
O31 O11 Cl 64.8(8) . . n
O41 O21 Cl 62.3(9) . . n
O41 O21 O31 104.5(11) . . n
Cl O21 O31 47.2(10) . . n
O41 O21 O31 104.5(11) . 11_655 n
Cl O21 O31 47.2(10) . 11_655 n
O31 O21 O31 42.3(17) . 11_655 n
O11 O31 O31 122.6(10) . 11_655 n
O11 O31 Cl 64.5(10) . . n
O31 O31 Cl 60.9(12) 11_655 . n
O11 O31 O21 90.7(15) . . n
O31 O31 O21 68.9(9) 11_655 . n
Cl O31 O21 51.4(9) . . n
O11 O31 O31 36.9(15) . 10_556 n
O31 O31 O31 90.000(5) 11_655 10_556 n
Cl O31 O31 46.9(11) . 10_556 n
O21 O31 O31 94.8(7) . 10_556 n
O21 O41 O21 139(2) . 10_556 n
O21 O41 Cl 69.3(10) . . n
O21 O41 Cl 69.3(10) 10_556 . n

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.24
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.074