# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004



data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Tatsuro Imakubo'
'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          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Synthesis of novel selenium-containing donors as
selenium analogues of diiodo(ethylenedithio)diselenadithiafulvalene
(DIETS)
;

data_diedsse
_database_code_depnum_ccdc_archive 'CCDC 236916'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H4 I2 Se6'
_chemical_formula_weight         827.67

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'
Se Se -0.0929 2.2259 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.9162(12)
_cell_length_b                   21.895(4)
_cell_length_c                   20.761(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.611(4)
_cell_angle_gamma                90.00
_cell_volume                     3142.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293
_cell_measurement_reflns_used    6391
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.85

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2896
_exptl_absorpt_coefficient_mu    17.874
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.0405
_exptl_absorpt_correction_T_max  0.3289
_exptl_absorpt_process_details   
;
SADABS; Sheldrick 1996
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293
_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
_diffrn_standards_number         236
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        2.0
_diffrn_reflns_number            23147
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0906
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         28.30
_reflns_number_total             7789
_reflns_number_gt                6157
_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 F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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/[σ²(Fo²)+(0.0353P)²+24.0725P] where P=(Fo²+2Fc²)/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_number_reflns         7789
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1321
_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

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
I1 I -0.01090(10) 1.28087(3) 0.35763(4) 0.0539(2) Uani 1 1 d . . .
I2 I 0.47230(11) 1.25931(3) 0.43403(4) 0.0531(2) Uani 1 1 d . . .
I3 I 0.48396(11) 0.79214(3) -0.24543(3) 0.05276(19) Uani 1 1 d . . .
I4 I 0.95396(11) 0.87368(4) -0.24459(4) 0.0572(2) Uani 1 1 d . . .
Se1 Se -0.09692(12) 1.13506(4) 0.40584(5) 0.0353(2) Uani 1 1 d . . .
Se2 Se 0.33288(15) 1.11455(4) 0.45999(6) 0.0502(3) Uani 1 1 d . . .
Se3 Se -0.15266(12) 0.97900(4) 0.39215(5) 0.0349(2) Uani 1 1 d . . .
Se4 Se 0.27573(12) 0.96019(4) 0.44731(4) 0.03277(19) Uani 1 1 d . . .
Se5 Se -0.17329(19) 0.84207(5) 0.33400(6) 0.0548(3) Uani 1 1 d . . .
Se6 Se 0.29009(17) 0.82087(5) 0.39704(7) 0.0582(3) Uani 1 1 d . . .
Se7 Se 0.41023(13) 0.86686(5) -0.10576(5) 0.0416(2) Uani 1 1 d . . .
Se8 Se 0.83024(15) 0.92683(5) -0.10011(5) 0.0481(3) Uani 1 1 d . . .
Se9 Se 0.34479(12) 0.90972(4) 0.05075(4) 0.03156(19) Uani 1 1 d . . .
Se10 Se 0.77428(13) 0.96170(4) 0.05897(5) 0.0379(2) Uani 1 1 d . . .
Se11 Se 0.3280(2) 0.89410(5) 0.20517(5) 0.0586(3) Uani 1 1 d . . .
Se12 Se 0.77619(16) 0.96316(5) 0.21454(5) 0.0471(2) Uani 1 1 d . . .
C1 C 0.0845(13) 1.2007(3) 0.4012(4) 0.0317(18) Uani 1 1 d . . .
C2 C 0.2610(13) 1.1918(4) 0.4251(5) 0.0352(19) Uani 1 1 d . . .
C3 C 0.1014(11) 1.0778(3) 0.4277(4) 0.0290(16) Uani 1 1 d . . .
C4 C 0.0799(11) 1.0171(3) 0.4220(4) 0.0263(15) Uani 1 1 d . . .
C5 C -0.0250(14) 0.9040(4) 0.3756(4) 0.0357(19) Uani 1 1 d . . .
C6 C 0.1534(14) 0.8963(3) 0.3995(4) 0.0343(18) Uani 1 1 d . . .
C7 C -0.111(2) 0.7789(7) 0.3977(9) 0.098(6) Uani 1 1 d . . .
H1 H -0.1890 0.7872 0.4349 0.117 Uiso 1 1 calc R . .
H2 H -0.1572 0.7405 0.3797 0.117 Uiso 1 1 calc R . .
C8 C 0.074(2) 0.7692(7) 0.4203(11) 0.106(7) Uani 1 1 d . . .
H3 H 0.1078 0.7278 0.4081 0.127 Uiso 1 1 calc R . .
H4 H 0.0697 0.7697 0.4669 0.127 Uiso 1 1 calc R . .
C9 C 0.5879(13) 0.8495(4) -0.1725(4) 0.0316(17) Uani 1 1 d . . .
C10 C 0.7594(13) 0.8760(4) -0.1701(4) 0.0353(19) Uani 1 1 d . . .
C11 C 0.6029(13) 0.9075(4) -0.0550(4) 0.0342(18) Uani 1 1 d . . .
C12 C 0.5798(11) 0.9228(3) 0.0066(4) 0.0272(15) Uani 1 1 d . . .
C13 C 0.4728(14) 0.9172(4) 0.1336(4) 0.0351(18) Uani 1 1 d . . .
C14 C 0.6527(13) 0.9389(4) 0.1361(4) 0.0364(19) Uani 1 1 d . . .
C15 C 0.387(2) 0.9613(6) 0.2638(6) 0.063(3) Uani 1 1 d . . .
H5 H 0.2693 0.9848 0.2692 0.076 Uiso 1 1 calc R . .
H6 H 0.4230 0.9442 0.3056 0.076 Uiso 1 1 calc R . .
C16 C 0.5425(17) 1.0041(5) 0.2444(5) 0.051(3) Uani 1 1 d . . .
H7 H 0.5777 1.0299 0.2808 0.062 Uiso 1 1 calc R . .
H8 H 0.4921 1.0303 0.2102 0.062 Uiso 1 1 calc R . .


_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
I1 C1 2.074(8) . ?
I2 C2 2.084(8) . ?
I3 C9 2.080(8) . ?
I4 C10 2.080(8) . ?
Se1 C3 1.904(8) . ?
Se1 C1 1.912(8) . ?
Se2 C3 1.897(8) . ?
Se2 C2 1.900(8) . ?
Se3 C5 1.900(9) . ?
Se3 C4 1.901(8) . ?
Se4 C6 1.901(9) . ?
Se4 C4 1.904(8) . ?
Se5 C5 1.894(9) . ?
Se5 C7 1.953(14) . ?
Se6 C6 1.904(8) . ?
Se6 C8 1.946(15) . ?
Se7 C11 1.897(9) . ?
Se7 C9 1.915(8) . ?
Se8 C10 1.883(9) . ?
Se8 C11 1.901(8) . ?
Se9 C12 1.910(8) . ?
Se9 C13 1.920(9) . ?
Se10 C14 1.897(9) . ?
Se10 C12 1.906(8) . ?
Se11 C13 1.883(8) . ?
Se11 C15 1.945(11) . ?
Se12 C14 1.893(9) . ?
Se12 C16 1.963(12) . ?
C1 C2 1.319(13) . ?
C3 C4 1.341(10) . ?
C5 C6 1.328(13) . ?
C7 C8 1.37(2) . ?
C7 H1 0.9700 . ?
C7 H2 0.9700 . ?
C8 H3 0.9700 . ?
C8 H4 0.9700 . ?
C9 C10 1.320(12) . ?
C11 C12 1.336(11) . ?
C13 C14 1.331(13) . ?
C15 C16 1.492(16) . ?
C15 H5 0.9700 . ?
C15 H6 0.9700 . ?
C16 H7 0.9700 . ?
C16 H8 0.9700 . ?

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 92.1(3) . . ?
C3 Se2 C2 91.9(4) . . ?
C5 Se3 C4 92.6(4) . . ?
C6 Se4 C4 92.0(4) . . ?
C5 Se5 C7 95.3(6) . . ?
C6 Se6 C8 96.4(5) . . ?
C11 Se7 C9 92.3(4) . . ?
C10 Se8 C11 92.7(4) . . ?
C12 Se9 C13 92.3(4) . . ?
C14 Se10 C12 92.4(4) . . ?
C13 Se11 C15 100.6(4) . . ?
C14 Se12 C16 92.5(4) . . ?
C2 C1 Se1 118.2(6) . . ?
C2 C1 I1 124.6(6) . . ?
Se1 C1 I1 117.2(4) . . ?
C1 C2 Se2 120.3(6) . . ?
C1 C2 I2 124.6(6) . . ?
Se2 C2 I2 115.0(5) . . ?
C4 C3 Se2 122.8(6) . . ?
C4 C3 Se1 123.6(6) . . ?
Se2 C3 Se1 113.6(4) . . ?
C3 C4 Se3 123.7(6) . . ?
C3 C4 Se4 123.2(6) . . ?
Se3 C4 Se4 113.0(4) . . ?
C6 C5 Se5 124.4(7) . . ?
C6 C5 Se3 118.3(6) . . ?
Se5 C5 Se3 116.9(5) . . ?
C5 C6 Se4 119.8(6) . . ?
C5 C6 Se6 123.9(6) . . ?
Se4 C6 Se6 116.0(5) . . ?
C8 C7 Se5 121.8(11) . . ?
C8 C7 H1 106.9 . . ?
Se5 C7 H1 106.9 . . ?
C8 C7 H2 106.9 . . ?
Se5 C7 H2 106.9 . . ?
H1 C7 H2 106.7 . . ?
C7 C8 Se6 122.9(11) . . ?
C7 C8 H3 106.6 . . ?
Se6 C8 H3 106.6 . . ?
C7 C8 H4 106.6 . . ?
Se6 C8 H4 106.6 . . ?
H3 C8 H4 106.6 . . ?
C10 C9 Se7 118.6(6) . . ?
C10 C9 I3 125.8(6) . . ?
Se7 C9 I3 115.5(4) . . ?
C9 C10 Se8 120.2(6) . . ?
C9 C10 I4 124.1(7) . . ?
Se8 C10 I4 115.4(4) . . ?
C12 C11 Se7 123.3(6) . . ?
C12 C11 Se8 122.6(7) . . ?
Se7 C11 Se8 114.1(4) . . ?
C11 C12 Se10 123.8(6) . . ?
C11 C12 Se9 123.2(6) . . ?
Se10 C12 Se9 112.9(4) . . ?
C14 C13 Se11 125.6(7) . . ?
C14 C13 Se9 118.2(7) . . ?
Se11 C13 Se9 116.2(5) . . ?
C13 C14 Se12 122.2(7) . . ?
C13 C14 Se10 119.8(7) . . ?
Se12 C14 Se10 116.9(5) . . ?
C16 C15 Se11 116.4(7) . . ?
C16 C15 H5 108.2 . . ?
Se11 C15 H5 108.2 . . ?
C16 C15 H6 108.2 . . ?
Se11 C15 H6 108.2 . . ?
H5 C15 H6 107.3 . . ?
C15 C16 Se12 114.0(8) . . ?
C15 C16 H7 108.8 . . ?
Se12 C16 H7 108.8 . . ?
C15 C16 H8 108.8 . . ?
Se12 C16 H8 108.8 . . ?
H7 C16 H8 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.610
_refine_diff_density_min         -2.263
_refine_diff_density_rms         0.265



