# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1lfjl4
_database_code_depnum_ccdc_archive 'CCDC 1472766'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;




_audit_creation_method           SHELXL-2013
_chemical_name_systematic        bis(TMS)selenophenedioxide

_chemical_name_common            bis(TMS)selenophenedioxide
_chemical_melting_point          '196 deg.C(decomp)'
_chemical_formula_moiety         'C10 H20 O2 Se Si2'
_chemical_formula_sum            'C10 H20 O2 Se Si2'
_chemical_formula_weight         307.40

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           81
_space_group_name_H-M_alt        'P -4'
_space_group_name_Hall           'P -4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'

_cell_length_a                   11.0742(16)
_cell_length_b                   11.0742(16)
_cell_length_c                   6.4127(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     786.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4115
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      28.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.523
_shelx_estimated_absorpt_T_min   0.518
_shelx_estimated_absorpt_T_max   0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4532
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (bruker)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART/APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            4426
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.177
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1826
_reflns_number_gt                1803
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
'Refined as a 2-component inversion twin., Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
w={1-exp[-9.0000(sinθ/λ)²)]}/[σ²(Fo²)+1.2676P]
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.24(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1826
_refine_ls_number_parameters     104
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.5000 0.0000 0.58860(7) 0.01711(15) Uani 1 2 d S T P . .
Si01 Si 0.29332(11) 0.20672(11) 0.72683(19) 0.0269(3) Uani 1 1 d . U . . .
O01 O 0.4140(3) -0.0859(3) 0.4477(5) 0.0293(6) Uani 1 1 d . . . . .
C01 C 0.4108(4) 0.0890(4) 0.7974(6) 0.0234(7) Uani 1 1 d . U . . .
C02 C 0.4524(4) 0.0477(4) 0.9780(7) 0.0270(9) Uani 1 1 d . . . . .
H02 H 0.4218 0.0785 1.1059 0.032 Uiso 1 1 calc R U . . .
C03 C 0.2868(12) 0.2123(12) 0.4350(16) 0.049(3) Uani 0.511(12) 1 d . U P A 1
H03A H 0.2285 0.2739 0.3914 0.074 Uiso 0.511(12) 1 calc R U P A 1
H03B H 0.2617 0.1334 0.3812 0.074 Uiso 0.511(12) 1 calc R U P A 1
H03C H 0.3668 0.2326 0.3799 0.074 Uiso 0.511(12) 1 calc R U P A 1
C04 C 0.3441(11) 0.3514(9) 0.8422(19) 0.041(3) Uani 0.511(12) 1 d . U P A 1
H04A H 0.2776 0.4099 0.8382 0.062 Uiso 0.511(12) 1 calc R U P A 1
H04B H 0.4126 0.3829 0.7623 0.062 Uiso 0.511(12) 1 calc R U P A 1
H04C H 0.3687 0.3381 0.9871 0.062 Uiso 0.511(12) 1 calc R U P A 1
C05 C 0.1487(9) 0.1564(11) 0.8432(19) 0.041(3) Uani 0.511(12) 1 d . U P A 1
H05A H 0.1614 0.1361 0.9903 0.062 Uiso 0.511(12) 1 calc R U P A 1
H05B H 0.1193 0.0851 0.7685 0.062 Uiso 0.511(12) 1 calc R U P A 1
H05C H 0.0891 0.2215 0.8323 0.062 Uiso 0.511(12) 1 calc R U P A 1
C23 C 0.2335(18) 0.2665(18) 0.972(2) 0.071(5) Uani 0.489(12) 1 d . U P A 2
H23A H 0.2990 0.3037 1.0521 0.107 Uiso 0.489(12) 1 calc R U P A 2
H23B H 0.1978 0.2006 1.0534 0.107 Uiso 0.489(12) 1 calc R U P A 2
H23C H 0.1714 0.3272 0.9422 0.107 Uiso 0.489(12) 1 calc R U P A 2
C24 C 0.1776(12) 0.1274(12) 0.568(3) 0.060(4) Uani 0.489(12) 1 d . U P A 2
H24A H 0.1229 0.0829 0.6603 0.090 Uiso 0.489(12) 1 calc R U P A 2
H24B H 0.2174 0.0708 0.4727 0.090 Uiso 0.489(12) 1 calc R U P A 2
H24C H 0.1314 0.1866 0.4872 0.090 Uiso 0.489(12) 1 calc R U P A 2
C25 C 0.3722(12) 0.3231(13) 0.568(3) 0.060(4) Uani 0.489(12) 1 d . U P A 2
H25A H 0.3126 0.3770 0.5042 0.090 Uiso 0.489(12) 1 calc R U P A 2
H25B H 0.4195 0.2835 0.4583 0.090 Uiso 0.489(12) 1 calc R U P A 2
H25C H 0.4263 0.3701 0.6577 0.090 Uiso 0.489(12) 1 calc R U P A 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
Se01 O01 1.622(3) . ?
Se01 O01 1.622(3) 2_655 ?
Se01 C01 1.934(4) 2_655 ?
Se01 C01 1.934(4) . ?
Si01 C23 1.831(14) . ?
Si01 C05 1.852(11) . ?
Si01 C04 1.852(11) . ?
Si01 C24 1.858(14) . ?
Si01 C25 1.861(14) . ?
Si01 C03 1.874(10) . ?
Si01 C01 1.896(4) . ?
C01 C02 1.328(6) . ?
C02 C02 1.493(9) 2_655 ?
C02 H02 0.9500 . ?
C03 H03A 0.9800 . ?
C03 H03B 0.9800 . ?
C03 H03C 0.9800 . ?
C04 H04A 0.9800 . ?
C04 H04B 0.9800 . ?
C04 H04C 0.9800 . ?
C05 H05A 0.9800 . ?
C05 H05B 0.9800 . ?
C05 H05C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
O01 Se01 O01 112.3(2) . 2_655 ?
O01 Se01 C01 112.73(17) . 2_655 ?
O01 Se01 C01 112.64(17) 2_655 2_655 ?
O01 Se01 C01 112.64(17) . . ?
O01 Se01 C01 112.74(17) 2_655 . ?
C01 Se01 C01 92.4(3) 2_655 . ?
C05 Si01 C04 111.2(6) . . ?
C23 Si01 C24 113.1(10) . . ?
C23 Si01 C25 113.0(10) . . ?
C24 Si01 C25 110.6(9) . . ?
C05 Si01 C03 112.3(6) . . ?
C04 Si01 C03 112.4(6) . . ?
C23 Si01 C01 107.0(4) . . ?
C05 Si01 C01 106.9(4) . . ?
C04 Si01 C01 106.9(4) . . ?
C24 Si01 C01 106.2(4) . . ?
C25 Si01 C01 106.5(4) . . ?
C03 Si01 C01 106.7(3) . . ?
C02 C01 Si01 133.1(3) . . ?
C02 C01 Se01 104.6(3) . . ?
Si01 C01 Se01 122.4(2) . . ?
C01 C02 C02 119.3(2) . 2_655 ?
C01 C02 H02 120.4 . . ?
C02 C02 H02 120.4 2_655 . ?
Si01 C03 H03A 109.5 . . ?
Si01 C03 H03B 109.5 . . ?
H03A C03 H03B 109.5 . . ?
Si01 C03 H03C 109.5 . . ?
H03A C03 H03C 109.5 . . ?
H03B C03 H03C 109.5 . . ?
Si01 C04 H04A 109.5 . . ?
Si01 C04 H04B 109.5 . . ?
H04A C04 H04B 109.5 . . ?
Si01 C04 H04C 109.5 . . ?
H04A C04 H04C 109.5 . . ?
H04B C04 H04C 109.5 . . ?
Si01 C05 H05A 109.5 . . ?
Si01 C05 H05B 109.5 . . ?
H05A C05 H05B 109.5 . . ?
Si01 C05 H05C 109.5 . . ?
H05A C05 H05C 109.5 . . ?
H05B C05 H05C 109.5 . . ?
Si01 C23 H23A 109.5 . . ?
Si01 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
Si01 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Si01 C24 H24A 109.5 . . ?
Si01 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
Si01 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Si01 C25 H25A 109.5 . . ?
Si01 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
Si01 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C23 Si01 C01 C02 -0.2(10) . . . . ?
C05 Si01 C01 C02 -59.6(6) . . . . ?
C04 Si01 C01 C02 59.6(6) . . . . ?
C24 Si01 C01 C02 -121.2(8) . . . . ?
C25 Si01 C01 C02 120.9(8) . . . . ?
C03 Si01 C01 C02 -179.9(7) . . . . ?
C23 Si01 C01 Se01 -180.0(9) . . . . ?
C05 Si01 C01 Se01 120.6(5) . . . . ?
C04 Si01 C01 Se01 -120.2(5) . . . . ?
C24 Si01 C01 Se01 59.0(7) . . . . ?
C25 Si01 C01 Se01 -58.9(7) . . . . ?
C03 Si01 C01 Se01 0.3(6) . . . . ?
Si01 C01 C02 C02 -180.0(4) . . . 2_655 ?
Se01 C01 C02 C02 -0.1(7) . . . 2_655 ?

_refine_diff_density_max         1.027
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran'
_chemical_compound_source        no
_chemical_properties_physical    ', Heat-sensitive,Photo-sensitive'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TMS2Seleno100K
_audit_block_doi                 10.5517/ccdc.csd.cc1lfjm5
_database_code_depnum_ccdc_archive 'CCDC 1472767'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,4-bisTMSselenophene
_chemical_name_common            1,4-bisTMSselenophene
_chemical_melting_point          '51-53 deg.C'
_chemical_formula_moiety         'C10 H20 Se Si2'
_chemical_formula_sum            'C10 H20 Se Si2'
_chemical_formula_weight         275.40

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'
Si Si 0.0817 0.0704 '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   Pmmn
_symmetry_Int_Tables_number      59
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2ab 2a'

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

_cell_length_a                   14.666(4)
_cell_length_b                   14.776(4)
_cell_length_c                   6.4741(16)
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_volume                     1403.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3416
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      26.88

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    2.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3994
_exptl_absorpt_correction_T_max  0.7664
_exptl_absorpt_process_details   'SADABS (Bruker)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 SMART-APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            6412
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         26.89
_reflns_number_total             1550
_reflns_number_gt                1408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0319P)²+0.5938P] where P=(Fo²+2Fc²)/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         1550
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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
Se1 Se 0.2500 0.2500 0.78890(5) 0.01769(11) Uani 1 4 d S . .
Si1 Si 0.2500 0.46426(4) 0.93921(10) 0.01628(15) Uani 1 2 d S . .
C01 C 0.2500 0.33973(15) 0.9928(3) 0.0157(5) Uani 1 2 d S . .
C02 C 0.2500 0.29821(16) 1.1823(4) 0.0173(5) Uani 1 2 d S . .
H02 H 0.2500 0.3320 1.3071 0.021 Uiso 1 2 calc SR . .
C03 C 0.2500 0.48364(18) 0.6558(4) 0.0262(6) Uani 1 2 d S . .
H03A H 0.1950 0.4569 0.5952 0.039 Uiso 0.50 1 calc PR . .
H03B H 0.3041 0.4554 0.5947 0.039 Uiso 0.50 1 calc PR . .
H03C H 0.2509 0.5488 0.6280 0.039 Uiso 1 2 calc SR . .
C04 C 0.35400(15) 0.51440(13) 1.0582(4) 0.0366(5) Uani 1 1 d . . .
H04A H 0.3532 0.5036 1.2075 0.055 Uiso 1 1 calc R . .
H04B H 0.3552 0.5797 1.0317 0.055 Uiso 1 1 calc R . .
H04C H 0.4084 0.4863 0.9980 0.055 Uiso 1 1 calc R . .
Se11 Se 0.2500 0.7500 0.80331(5) 0.01513(11) Uani 1 4 d S . .
Si11 Si 0.03410(4) 0.7500 0.64815(10) 0.01661(15) Uani 1 2 d S . .
C11 C 0.15983(15) 0.7500 0.5985(3) 0.0164(5) Uani 1 2 d S . .
C12 C 0.20161(17) 0.7500 0.4112(4) 0.0299(6) Uani 1 2 d S . .
H12 H 0.1677 0.7500 0.2862 0.036 Uiso 1 2 calc SR . .
C13 C 0.01068(16) 0.7500 0.9310(4) 0.0229(5) Uani 1 2 d S . .
H13A H 0.0366 0.8047 0.9934 0.034 Uiso 0.50 1 calc PR . .
H13B H 0.0385 0.6964 0.9942 0.034 Uiso 0.50 1 calc PR . .
H13C H -0.0553 0.7489 0.9543 0.034 Uiso 1 2 calc SR . .
C14 C -0.01487(13) 0.85335(14) 0.5266(3) 0.0312(5) Uani 1 1 d . . .
H14A H 0.0114 0.9073 0.5917 0.047 Uiso 1 1 calc R . .
H14B H -0.0812 0.8536 0.5454 0.047 Uiso 1 1 calc R . .
H14C H -0.0006 0.8536 0.3787 0.047 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
Se1 C01 1.871(2) . ?
Se1 C01 1.871(2) 2 ?
Si1 C03 1.857(3) . ?
Si1 C04 1.862(2) . ?
Si1 C04 1.862(2) 7_655 ?
Si1 C01 1.873(2) . ?
C01 C02 1.372(3) . ?
C02 C02 1.425(5) 2 ?
C02 H02 0.9500 . ?
C03 H03A 0.9800 . ?
C03 H03B 0.9800 . ?
C03 H03C 0.9800 . ?
C04 H04A 0.9800 . ?
C04 H04B 0.9800 . ?
C04 H04C 0.9800 . ?
Se11 C11 1.872(2) . ?
Se11 C11 1.872(2) 2_565 ?
Si11 C14 1.8620(19) . ?
Si11 C14 1.8620(19) 8_575 ?
Si11 C13 1.863(3) . ?
Si11 C11 1.872(2) . ?
C11 C12 1.359(3) . ?
C12 C12 1.419(5) 2_565 ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C01 Se1 C01 90.24(14) . 2 ?
C03 Si1 C04 110.32(9) . . ?
C03 Si1 C04 110.32(8) . 7_655 ?
C04 Si1 C04 109.96(15) . 7_655 ?
C03 Si1 C01 109.55(11) . . ?
C04 Si1 C01 108.31(8) . . ?
C04 Si1 C01 108.31(8) 7_655 . ?
C02 C01 Se1 108.31(16) . . ?
C02 C01 Si1 127.25(18) . . ?
Se1 C01 Si1 124.44(13) . . ?
C01 C02 C02 116.57(14) . 2 ?
C01 C02 H02 121.7 . . ?
C02 C02 H02 121.7 2 . ?
Si1 C03 H03A 109.5 . . ?
Si1 C03 H03B 109.5 . . ?
H03A C03 H03B 109.5 . . ?
Si1 C03 H03C 109.5 . . ?
H03A C03 H03C 109.5 . . ?
H03B C03 H03C 109.5 . . ?
Si1 C04 H04A 109.5 . . ?
Si1 C04 H04B 109.5 . . ?
H04A C04 H04B 109.5 . . ?
Si1 C04 H04C 109.5 . . ?
H04A C04 H04C 109.5 . . ?
H04B C04 H04C 109.5 . . ?
C11 Se11 C11 89.86(14) . 2_565 ?
C14 Si11 C14 110.20(13) . 8_575 ?
C14 Si11 C13 110.14(7) . . ?
C14 Si11 C13 110.14(7) 8_575 . ?
C14 Si11 C11 107.90(7) . . ?
C14 Si11 C11 107.90(7) 8_575 . ?
C13 Si11 C11 110.50(10) . . ?
C12 C11 Se11 108.27(17) . . ?
C12 C11 Si11 126.68(18) . . ?
Se11 C11 Si11 125.05(12) . . ?
C11 C12 C12 116.80(14) . 2_565 ?
C11 C12 H12 121.6 . . ?
C12 C12 H12 121.6 2_565 . ?
Si11 C13 H13A 109.5 . . ?
Si11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Si11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si11 C14 H14A 109.5 . . ?
Si11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.086
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method EtOH
