#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/02/7110282.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7110282
loop_
_publ_author_name
'Imakubo, Tatsuro'
'Shirahata, Takashi'
'Kibune, Megumi'
_publ_section_title
;
 Synthesis, crystal structure and electrochemical properties of
 bis(ethylenedioxy)tetraselenafulvalene (BEDO-TSeF)
;
_journal_issue                   14
_journal_name_full               'Chemical Communications'
_journal_page_first              1590
_journal_page_last               1591
_journal_paper_doi               10.1039/b403559c
_journal_year                    2004
_chemical_formula_moiety         C10H8O4Se4
_chemical_formula_sum            'C10 H8 O4 Se4'
_chemical_formula_weight         508.00
_chemical_name_common            BEDO-TSeF
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7348(4)
_cell_length_b                   7.8387(5)
_cell_length_c                   21.9084(13)
_cell_measurement_reflns_used    3844
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.60
_cell_volume                     1328.32(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.366[pixels/mm]
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10056
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    11.049
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.540
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0421P)²+3.1236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2915
_reflns_number_total             3311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b403559csup1.cif
_cod_data_source_block           bedo-tsef
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7110282
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'
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
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)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11375614
