# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Tatsuro Imakubo'
'Megumi Kibune'
'Takashi Shirahata'

_publ_contact_author_name        'Dr Tatsuro Imakubo'
_publ_contact_author_address     
;
Imakubo Initiative Research Unit
RIKEN
2-1 Hirosawa
Wako
Saitama
351-0198
JAPAN
;

_publ_contact_author_email       IMAKUBO@RIKEN.JP

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Synthesis, crystal structure and electrochemical
properties of bis(ethylenedioxy)tetraselenafulvalene (BEDO-TSeF)
;

data_bedo-tsef
_database_code_depnum_ccdc_archive 'CCDC 233921'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            BEDO-TSeF
_chemical_melting_point          ?
_chemical_formula_moiety         C10H8O4Se4
_chemical_formula_sum            'C10 H8 O4 Se4'
_chemical_formula_weight         508.00

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.7348(4)
_cell_length_b                   7.8387(5)
_cell_length_c                   21.9084(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1328.32(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3844
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.50

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    2.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    11.049
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366[pixels/mm]
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10056
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         28.33
_reflns_number_total             3311
_reflns_number_gt                2915
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0421P)^2^+3.1236P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.01(3)
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

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
Se1 Se 0.34208(8) 0.97534(10) 0.10237(3) 0.04336(17) Uani 1 1 d . . .
Se3 Se 0.07625(8) 0.96356(11) 0.22412(3) 0.04870(19) Uani 1 1 d . . .
Se2 Se 0.02894(8) 0.87666(10) 0.01377(3) 0.04531(18) Uani 1 1 d . . .
Se4 Se -0.23458(9) 0.84328(10) 0.13678(3) 0.0491(2) Uani 1 1 d . . .
C1 C 0.1037(8) 0.9186(8) 0.0949(3) 0.0374(13) Uani 1 1 d . . .
C3 C 0.3481(8) 1.0455(8) 0.0196(3) 0.0377(12) Uani 1 1 d . . .
O1 O 0.4939(6) 1.1299(7) 0.0023(2) 0.0496(12) Uani 1 1 d . . .
C2 C 0.0004(8) 0.9093(8) 0.1440(3) 0.0364(12) Uani 1 1 d . . .
C4 C 0.2170(8) 1.0077(8) -0.0166(3) 0.0379(12) Uani 1 1 d . . .
O2 O 0.2063(7) 1.0554(6) -0.0766(2) 0.0494(12) Uani 1 1 d . . .
C5 C -0.1548(8) 0.9663(9) 0.2530(3) 0.0419(13) Uani 1 1 d . . .
O4 O -0.4518(6) 0.9090(8) 0.2346(2) 0.0538(13) Uani 1 1 d . . .
O3 O -0.1715(6) 1.0091(7) 0.3132(2) 0.0532(12) Uani 1 1 d . . .
C6 C -0.2809(8) 0.9202(8) 0.2170(3) 0.0400(14) Uani 1 1 d . . .
C8 C 0.3401(11) 1.1763(11) -0.0912(3) 0.060(2) Uani 1 1 d . . .
H8A H 0.3061 1.2885 -0.0770 0.072 Uiso 1 1 calc R . .
H8B H 0.3541 1.1819 -0.1352 0.072 Uiso 1 1 calc R . .
C9 C -0.3492(10) 1.0231(16) 0.3288(4) 0.080(3) Uani 1 1 d . . .
H9A H -0.3605 1.0051 0.3724 0.096 Uiso 1 1 calc R . .
H9B H -0.3862 1.1389 0.3203 0.096 Uiso 1 1 calc R . .
C10 C -0.4637(11) 0.9102(17) 0.2987(3) 0.088(4) Uani 1 1 d . . .
H10A H -0.4422 0.7956 0.3135 0.106 Uiso 1 1 calc R . .
H10B H -0.5811 0.9403 0.3099 0.106 Uiso 1 1 calc R . .
C7 C 0.5063(11) 1.1289(11) -0.0630(3) 0.0576(19) Uani 1 1 d . . .
H7A H 0.5398 1.0160 -0.0767 0.069 Uiso 1 1 calc R . .
H7B H 0.5950 1.2087 -0.0758 0.069 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.0288(3) 0.0668(4) 0.0345(3) 0.0058(3) -0.0013(2) 0.0002(3)
Se3 0.0330(3) 0.0783(5) 0.0348(3) -0.0028(3) -0.0018(2) -0.0045(3)
Se2 0.0404(3) 0.0596(4) 0.0359(3) -0.0069(3) 0.0020(3) -0.0161(3)
Se4 0.0379(3) 0.0706(5) 0.0388(3) -0.0180(3) 0.0078(3) -0.0183(3)
C1 0.031(3) 0.045(3) 0.036(3) -0.001(3) 0.001(2) -0.002(2)
C3 0.037(3) 0.043(3) 0.033(3) 0.001(3) 0.004(2) -0.002(3)
O1 0.040(2) 0.068(3) 0.041(2) -0.001(2) 0.0033(19) -0.017(2)
C2 0.033(3) 0.040(3) 0.037(3) 0.002(2) -0.001(2) -0.003(2)
C4 0.041(3) 0.043(3) 0.029(3) -0.007(3) 0.005(2) -0.006(2)
O2 0.060(3) 0.057(3) 0.031(2) -0.002(2) -0.002(2) -0.009(2)
C5 0.038(3) 0.054(4) 0.034(3) -0.003(3) 0.002(2) 0.001(3)
O4 0.035(2) 0.091(4) 0.035(2) -0.001(2) 0.0058(19) -0.005(2)
O3 0.048(2) 0.081(4) 0.031(2) -0.005(2) 0.0009(19) 0.001(3)
C6 0.034(3) 0.053(4) 0.033(3) 0.002(3) 0.004(2) -0.001(3)
C8 0.075(5) 0.064(5) 0.042(4) 0.009(3) 0.010(4) -0.012(4)
C9 0.053(4) 0.137(9) 0.050(4) -0.023(6) 0.005(4) 0.014(6)
C10 0.053(4) 0.176(12) 0.036(4) -0.005(5) 0.013(4) -0.010(6)
C7 0.061(4) 0.069(5) 0.043(4) -0.003(4) 0.015(3) -0.022(4)

_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
Se1 C3 1.896(6) . ?
Se1 C1 1.904(6) . ?
Se3 C5 1.896(6) . ?
Se3 C2 1.900(6) . ?
Se2 C1 1.899(6) . ?
Se2 C4 1.901(6) . ?
Se4 C6 1.892(6) . ?
Se4 C2 1.896(6) . ?
C1 C2 1.340(8) . ?
C3 C4 1.321(8) . ?
C3 O1 1.361(7) . ?
O1 C7 1.433(8) . ?
C4 O2 1.369(7) . ?
O2 C8 1.440(9) . ?
C5 C6 1.306(9) . ?
C5 O3 1.368(7) . ?
O4 C6 1.380(7) . ?
O4 C10 1.407(9) . ?
O3 C9 1.420(9) . ?
C8 C7 1.474(12) . ?
C9 C10 1.414(13) . ?

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 Se1 C1 90.6(3) . . ?
C5 Se3 C2 91.1(3) . . ?
C1 Se2 C4 90.1(3) . . ?
C6 Se4 C2 91.0(3) . . ?
C2 C1 Se2 124.0(4) . . ?
C2 C1 Se1 121.4(5) . . ?
Se2 C1 Se1 114.5(3) . . ?
C4 C3 O1 125.4(5) . . ?
C4 C3 Se1 119.3(5) . . ?
O1 C3 Se1 115.3(4) . . ?
C3 O1 C7 109.3(5) . . ?
C1 C2 Se4 121.3(5) . . ?
C1 C2 Se3 123.0(4) . . ?
Se4 C2 Se3 115.7(3) . . ?
C3 C4 O2 124.1(6) . . ?
C3 C4 Se2 119.9(5) . . ?
O2 C4 Se2 115.9(4) . . ?
C4 O2 C8 110.5(5) . . ?
C6 C5 O3 125.4(6) . . ?
C6 C5 Se3 120.0(5) . . ?
O3 C5 Se3 114.5(4) . . ?
C6 O4 C10 110.0(6) . . ?
C5 O3 C9 110.0(5) . . ?
C5 C6 O4 124.3(6) . . ?
C5 C6 Se4 120.5(5) . . ?
O4 C6 Se4 114.9(4) . . ?
O2 C8 C7 111.6(6) . . ?
C10 C9 O3 116.5(8) . . ?
O4 C10 C9 115.4(8) . . ?
O1 C7 C8 111.0(6) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.097