# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_sse1
_database_code_depnum_ccdc_archive 'CCDC 1412304'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            'thiophenol-selenophenol alloy'
_chemical_melting_point          ?
_chemical_formula_moiety         '(C6 H6 S)0.95, (C6 H6 Se)0.05'
_chemical_formula_sum            'C6 H6 S0.95 Se0.05'
_chemical_formula_weight         112.52
_chemical_compound_source        'see text'

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'
S S 0.1246 0.1234 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_Int_Tables_number      60

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z
_cell_length_a                   13.8535(14)
_cell_length_b                   11.4448(13)
_cell_length_c                   7.1913(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1140.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3699
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             471
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_min  0.8118
_exptl_absorpt_correction_T_max  0.8118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            3699
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1125
_reflns_number_gt                903
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

_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 > 2σ(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)+(0.0000P)²+3.7967P] 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         1125
_refine_ls_number_parameters     70
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.226
_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
C1 C 0.2714(3) 0.1198(3) 0.4436(5) 0.0204(8) Uani 1 1 d . . .
C5 C 0.1226(3) 0.0565(4) 0.5757(6) 0.0282(10) Uani 1 1 d . . .
H5 H 0.0876 0.0013 0.6427 0.034 Uiso 1 1 calc R . .
C2 C 0.2260(3) 0.2197(3) 0.3793(6) 0.0261(9) Uani 1 1 d . . .
H2 H 0.2611 0.2759 0.3152 0.031 Uiso 1 1 calc R . .
C3 C 0.1287(3) 0.2358(4) 0.4100(7) 0.0338(11) Uani 1 1 d . . .
H3 H 0.0979 0.3015 0.3623 0.041 Uiso 1 1 calc R . .
C4 C 0.0767(3) 0.1549(4) 0.5114(7) 0.0325(11) Uani 1 1 d . . .
H4 H 0.0115 0.1669 0.5358 0.039 Uiso 1 1 calc R . .
C6 C 0.2194(3) 0.0379(3) 0.5431(5) 0.0228(9) Uani 1 1 d . . .
H6 H 0.2495 -0.0292 0.5875 0.027 Uiso 1 1 calc R . .
S1 S 0.3968(2) 0.09476(16) 0.4012(6) 0.0302(5) Uani 0.95 1 d P . .
Se1 Se 0.393(2) 0.120(2) 0.395(5) 0.0302(5) Uani 0.05 1 d PD . .
H1 H 0.412(3) 0.023(3) 0.518(6) 0.036 Uiso 1 1 d D . .

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
C1 0.0220(18) 0.027(2) 0.0125(18) -0.0040(15) -0.0029(15) -0.0022(15)
C5 0.032(2) 0.031(2) 0.022(2) -0.0057(18) 0.0084(18) -0.0120(17)
C2 0.036(2) 0.021(2) 0.022(2) -0.0004(17) 0.0006(18) -0.0048(17)
C3 0.041(2) 0.023(2) 0.037(3) -0.006(2) -0.009(2) 0.0105(18)
C4 0.019(2) 0.037(3) 0.041(3) -0.015(2) 0.0005(19) -0.0004(18)
C6 0.030(2) 0.0194(19) 0.019(2) -0.0013(16) -0.0036(16) -0.0033(16)
S1 0.0199(6) 0.0310(13) 0.0396(7) -0.0012(12) 0.0024(5) -0.0010(10)
Se1 0.0199(6) 0.0310(13) 0.0396(7) -0.0012(12) 0.0024(5) -0.0010(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.382(5) . ?
C1 C2 1.384(6) . ?
C1 Se1 1.73(3) . ?
C1 S1 1.787(5) . ?
C5 C4 1.373(6) . ?
C5 C6 1.379(6) . ?
C5 H5 0.9300 . ?
C2 C3 1.378(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(7) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
S1 H1 1.19(3) . ?
Se1 H1 1.441(19) . ?

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
C6 C1 C2 119.7(4) . . ?
C6 C1 Se1 128.1(9) . . ?
C2 C1 Se1 112.1(9) . . ?
C6 C1 S1 119.1(3) . . ?
C2 C1 S1 121.2(3) . . ?
Se1 C1 S1 9.5(8) . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C6 C1 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C1 S1 H1 99(2) . . ?
C1 Se1 H1 93(2) . . ?

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
C6 C1 C2 C3 -1.7(6) . . . . ?
Se1 C1 C2 C3 -178.4(13) . . . . ?
S1 C1 C2 C3 178.5(4) . . . . ?
C1 C2 C3 C4 2.6(7) . . . . ?
C6 C5 C4 C3 0.8(6) . . . . ?
C2 C3 C4 C5 -2.1(7) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
Se1 C1 C6 C5 176.5(15) . . . . ?
S1 C1 C6 C5 -179.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.078

#===END
####################################################################### 
# 
# 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_sse9p
_database_code_depnum_ccdc_archive 'CCDC 1412305'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C6 H6 S)0.91, (C6 H6 Se)0.09'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C6 H6 S0.91 Se0.09'
_chemical_formula_iupac          ?
_chemical_formula_weight         114.40
_chemical_compound_source        'see text'

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'
S S 0.1246 0.1234 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_Int_Tables_number      60

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z
_cell_length_a                   13.856(4)
_cell_length_b                   11.425(3)
_cell_length_c                   7.1934(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1138.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    15534
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             477
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_min  0.7602
_exptl_absorpt_correction_T_max  0.7602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            15534
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1122
_reflns_number_gt                812
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

_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 > 2σ(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)+(0.0742P)²+4.0811P] 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         1122
_refine_ls_number_parameters     70
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2098
_refine_ls_wR_factor_gt          0.2004
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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
C1 C 0.2711(4) 0.1204(4) 0.4449(7) 0.0298(12) Uani 1 1 d . . .
C3 C 0.1234(4) 0.0554(5) 0.5750(8) 0.0393(14) Uani 1 1 d . . .
H3 H 0.0886 -0.0007 0.6406 0.047 Uiso 1 1 calc R . .
C6 C 0.2256(4) 0.2190(5) 0.3783(7) 0.0373(14) Uani 1 1 d . . .
H6 H 0.2601 0.2746 0.3112 0.045 Uiso 1 1 calc R . .
C5 C 0.1286(4) 0.2348(5) 0.4119(8) 0.0427(15) Uani 1 1 d . . .
H5 H 0.0976 0.3010 0.3661 0.051 Uiso 1 1 calc R . .
C4 C 0.0772(4) 0.1538(5) 0.5122(10) 0.0449(16) Uani 1 1 d . . .
H4 H 0.0121 0.1656 0.5372 0.054 Uiso 1 1 calc R . .
C2 C 0.2187(4) 0.0381(4) 0.5432(7) 0.0307(12) Uani 1 1 d . . .
H2 H 0.2489 -0.0291 0.5875 0.037 Uiso 1 1 calc R . .
S1 S 0.3954(5) 0.0987(7) 0.3952(7) 0.0354(8) Uani 0.91 1 d P . .
Se1 Se 0.402(2) 0.093(3) 0.429(4) 0.0354(8) Uani 0.09 1 d PD . .
H1 H 0.459(4) 0.101(4) 0.599(5) 0.042 Uiso 1 1 d D . .

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
C1 0.039(3) 0.028(3) 0.022(3) -0.009(2) -0.001(2) -0.005(2)
C3 0.055(4) 0.033(3) 0.029(3) -0.001(3) 0.004(3) -0.013(3)
C6 0.060(4) 0.022(3) 0.030(3) 0.002(2) -0.002(3) -0.003(2)
C5 0.061(4) 0.025(3) 0.042(3) -0.006(3) -0.007(3) 0.010(3)
C4 0.039(3) 0.042(3) 0.054(4) -0.019(3) 0.001(3) -0.001(3)
C2 0.050(3) 0.020(2) 0.022(3) 0.002(2) -0.003(2) -0.005(2)
S1 0.0343(13) 0.0399(12) 0.032(2) -0.0018(18) -0.0003(15) -0.0029(10)
Se1 0.0343(13) 0.0399(12) 0.032(2) -0.0018(18) -0.0003(15) -0.0029(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.377(8) . ?
C1 C2 1.383(7) . ?
C1 S1 1.776(9) . ?
C1 Se1 1.84(4) . ?
C3 C2 1.355(8) . ?
C3 C4 1.371(9) . ?
C3 H3 0.9300 . ?
C6 C5 1.378(8) . ?
C6 H6 0.9300 . ?
C5 C4 1.372(9) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
S1 H1 1.71(3) . ?
Se1 H1 1.46(2) . ?

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
C6 C1 C2 119.6(5) . . ?
C6 C1 S1 119.2(5) . . ?
C2 C1 S1 121.1(5) . . ?
C6 C1 Se1 124.6(12) . . ?
C2 C1 Se1 115.7(11) . . ?
S1 C1 Se1 8.2(9) . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C1 C6 C5 119.5(5) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C3 C4 C5 119.0(6) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 S1 H1 109(2) . . ?
C1 Se1 H1 118(3) . . ?

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
C2 C1 C6 C5 0.5(8) . . . . ?
S1 C1 C6 C5 178.2(5) . . . . ?
Se1 C1 C6 C5 -174.5(12) . . . . ?
C1 C6 C5 C4 0.6(8) . . . . ?
C2 C3 C4 C5 1.4(9) . . . . ?
C6 C5 C4 C3 -1.5(9) . . . . ?
C4 C3 C2 C1 -0.4(8) . . . . ?
C6 C1 C2 C3 -0.6(8) . . . . ?
S1 C1 C2 C3 -178.3(5) . . . . ?
Se1 C1 C2 C3 174.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.097


#===END
####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1412306'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
#==============================================================================

# 0. AUDIT DETAILS

_audit_creation_date             'Jul 10 21:26:40 2015'
_audit_creation_method           'PLATON <TABLE ACC> option'

_chemical_name_systematic        
;
 thiophenol-selenophenol
;
_chemical_name_common            'thiophenol-selenophenol alloy'
_chemical_melting_point          ?
_chemical_formula_moiety         '(C6 H6 S)0.75, (C6 H6 Se)0.25'
_chemical_formula_sum            'C6 H6 S0.75 Se0.25'
_chemical_formula_iupac          ?
_chemical_formula_weight         121.90
_chemical_compound_source        'see text'

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'
S S 0.1246 0.1234 ' 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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2n'
_symmetry_space_group_name_H-M   'P n a b'
_symmetry_Int_Tables_number      60

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2+x,1/2-y,1/2-z
3 -x,1/2-y,1/2+z
4 1/2-x,y,-z
5 -x,-y,-z
6 1/2-x,1/2+y,1/2+z
7 x,1/2+y,1/2-z
8 1/2+x,-y,z

_cell_length_a                   7.2109(10)
_cell_length_b                   11.3897(16)
_cell_length_c                   13.9705(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1147.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    10491
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.99


_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_T_min  0.5971
_exptl_absorpt_correction_T_max  0.5971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            10491
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1132
_reflns_number_gt                1066
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

_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 > 2σ(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)+(0.0000P)²+8.3456P] 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         1132
_refine_ls_number_parameters     70
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.389
_refine_ls_restrained_S_all      1.388
_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
C3 C 0.0876(9) 0.7649(5) 0.8726(4) 0.0323(14) Uani 1 1 d . . .
H3 H 0.1356 0.6978 0.9044 0.039 Uiso 1 1 calc R . .
C1 C 0.0547(7) 0.8796(4) 0.7301(4) 0.0191(11) Uani 1 1 d . . .
C2 C 0.1185(8) 0.7799(5) 0.7760(4) 0.0270(12) Uani 1 1 d . . .
H2 H 0.1837 0.7216 0.7408 0.032 Uiso 1 1 calc R . .
C5 C -0.0770(8) 0.9458(5) 0.8766(4) 0.0295(13) Uani 1 1 d . . .
H5 H -0.1453 1.0028 0.9115 0.035 Uiso 1 1 calc R . .
C6 C -0.0441(7) 0.9632(5) 0.7806(4) 0.0220(11) Uani 1 1 d . . .
H6 H -0.0885 1.0318 0.7495 0.026 Uiso 1 1 calc R . .
C4 C -0.0127(9) 0.8471(5) 0.9228(4) 0.0345(15) Uani 1 1 d . . .
H4 H -0.0375 0.8358 0.9890 0.041 Uiso 1 1 calc R . .
S1 S 0.1136(17) 0.8982(17) 0.6063(12) 0.0205(13) Uani 0.75 1 d PD . .
Se1 Se 0.079(2) 0.905(2) 0.5992(15) 0.0205(13) Uani 0.25 1 d P . .
H1 H -0.033(5) 0.962(4) 0.584(4) 0.025 Uiso 1 1 d D . .

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
C3 0.037(3) 0.022(3) 0.039(3) 0.007(2) -0.006(3) -0.007(3)
C1 0.010(2) 0.022(3) 0.025(3) -0.002(2) -0.0014(19) -0.0057(19)
C2 0.025(3) 0.018(3) 0.038(3) -0.004(2) 0.002(2) 0.002(2)
C5 0.024(3) 0.029(3) 0.035(3) -0.010(2) 0.007(3) -0.006(2)
C6 0.014(2) 0.019(2) 0.032(3) -0.004(2) -0.003(2) 0.000(2)
C4 0.042(4) 0.035(3) 0.027(3) -0.001(3) 0.003(3) -0.017(3)
S1 0.013(4) 0.0317(19) 0.016(2) -0.0005(15) -0.004(3) 0.004(3)
Se1 0.013(4) 0.0317(19) 0.016(2) -0.0005(15) -0.004(3) 0.004(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C3 C4 1.376(9) . ?
C3 C2 1.379(8) . ?
C3 H3 0.9500 . ?
C1 C2 1.383(7) . ?
C1 C6 1.383(7) . ?
C1 S1 1.793(19) . ?
C1 Se1 1.86(2) . ?
C2 H2 0.9500 . ?
C5 C6 1.376(8) . ?
C5 C4 1.377(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
S1 H1 1.32(2) . ?
Se1 H1 1.06(3) . ?

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
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C1 C6 120.0(5) . . ?
C2 C1 S1 117.7(7) . . ?
C6 C1 S1 122.2(7) . . ?
C2 C1 Se1 123.5(8) . . ?
C6 C1 Se1 116.4(7) . . ?
S1 C1 Se1 8.5(8) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.1(5) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C3 C4 C5 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C1 S1 H1 96(3) . . ?
C1 Se1 H1 103(3) . . ?

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
C4 C3 C2 C1 2.4(9) . . . . ?
C6 C1 C2 C3 -1.5(8) . . . . ?
S1 C1 C2 C3 175.8(7) . . . . ?
Se1 C1 C2 C3 -177.0(8) . . . . ?
C4 C5 C6 C1 0.3(8) . . . . ?
C2 C1 C6 C5 0.1(8) . . . . ?
S1 C1 C6 C5 -177.0(7) . . . . ?
Se1 C1 C6 C5 175.9(8) . . . . ?
C2 C3 C4 C5 -1.9(9) . . . . ?
C6 C5 C4 C3 0.6(9) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.110


#===END
####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1412307'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
#==============================================================================

# 0. AUDIT DETAILS

_audit_creation_date             'Jul 11 00:35:59 2015'
_audit_creation_method           'PLATON <TABLE ACC> option'

_chemical_name_systematic        
;
 benzene selenol
;
_chemical_name_common            selenophenol
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 Se'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C6 H6 Se'
_chemical_formula_iupac          ?
_chemical_formula_weight         157.07
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2n'
_symmetry_space_group_name_H-M   'P n a b'
_symmetry_Int_Tables_number      60

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2+x,1/2-y,1/2-z
3 -x,1/2-y,1/2+z
4 1/2-x,y,-z
5 -x,-y,-z
6 1/2-x,1/2+y,1/2+z
7 x,1/2+y,1/2-z
8 1/2+x,-y,z
_cell_length_a                   7.329(4)
_cell_length_b                   11.226(5)
_cell_length_c                   14.422(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1186.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9821
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    6.191
_exptl_absorpt_correction_T_min  0.2582
_exptl_absorpt_correction_T_max  0.2582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9821
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1044
_reflns_number_gt                881
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0000P)²+30.7064P] 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         1044
_refine_ls_number_parameters     49
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2073
_refine_ls_wR_factor_gt          0.2037
_refine_ls_goodness_of_fit_ref   1.345
_refine_ls_restrained_S_all      1.344
_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
C1 C 0.0457(18) 0.6226(12) 0.2666(8) 0.0292(5) Uani 1 1 d . . .
C2 C -0.0468(15) 0.5344(11) 0.2209(8) 0.0221(19) Uani 1 1 d D . .
H2 H -0.0853 0.4664 0.2521 0.027 Uiso 1 1 calc R . .
C3 C -0.0820(16) 0.5487(11) 0.1268(8) 0.0221(19) Uani 1 1 d . . .
H3 H -0.1502 0.4910 0.0961 0.027 Uiso 1 1 calc R . .
C4 C -0.0205(19) 0.6435(11) 0.0785(9) 0.029(3) Uani 1 1 d . . .
H4 H -0.0452 0.6506 0.0155 0.034 Uiso 1 1 calc R . .
C5 C 0.0828(18) 0.7326(10) 0.1252(8) 0.0227(19) Uani 1 1 d . . .
H5 H 0.1284 0.7980 0.0931 0.027 Uiso 1 1 calc R . .
C6 C 0.1137(17) 0.7199(10) 0.2188(8) 0.0227(19) Uani 1 1 d D . .
H6 H 0.1810 0.7773 0.2503 0.027 Uiso 1 1 calc R . .
Se1 Se 0.09451(18) 0.60507(12) 0.39651(8) 0.0292(5) Uani 1 1 d D . .
H1 H 0.272(6) 0.563(6) 0.413(3) 0.035 Uiso 1 1 d D . .

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
C1 0.0321(8) 0.0407(8) 0.0147(7) -0.0052(6) -0.0003(6) -0.0017(6)
C2 0.016(4) 0.026(5) 0.024(4) -0.005(4) -0.001(4) 0.000(4)
C3 0.016(4) 0.026(5) 0.024(4) -0.005(4) -0.001(4) 0.000(4)
C4 0.043(8) 0.022(7) 0.021(7) 0.002(5) -0.009(6) 0.012(6)
C5 0.033(5) 0.010(4) 0.025(4) -0.001(3) -0.004(4) 0.006(4)
C6 0.033(5) 0.010(4) 0.025(4) -0.001(3) -0.004(4) 0.006(4)
Se1 0.0321(8) 0.0407(8) 0.0147(7) -0.0052(6) -0.0003(6) -0.0017(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.370(17) . ?
C1 C6 1.385(18) . ?
C1 Se1 1.917(12) . ?
C2 C3 1.390(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.423(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
Se1 H1 1.41(4) . ?

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
C2 C1 C6 120.5(12) . . ?
C2 C1 Se1 119.3(10) . . ?
C6 C1 Se1 120.1(10) . . ?
C1 C2 C3 118.6(12) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 122.2(12) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.2(12) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 118.6(12) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.8(12) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C1 Se1 H1 112(2) . . ?

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
C6 C1 C2 C3 -4.4(18) . . . . ?
Se1 C1 C2 C3 179.7(9) . . . . ?
C1 C2 C3 C4 3.3(18) . . . . ?
C2 C3 C4 C5 -0.5(19) . . . . ?
C3 C4 C5 C6 -1.1(19) . . . . ?
C4 C5 C6 C1 -0.1(19) . . . . ?
C2 C1 C6 C5 2.9(19) . . . . ?
Se1 C1 C6 C5 178.8(10) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.160
_refine_diff_density_min         -1.486
_refine_diff_density_rms         0.194
#===END
####################################################################### 
# 
# 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_phs
_database_code_depnum_ccdc_archive 'CCDC 1412308'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            thiophenol
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C6 H6 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         110.18
_chemical_compound_source        'see text'

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'
S S 0.1246 0.1234 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2n'
_symmetry_space_group_name_H-M   'P n a b'
_symmetry_Int_Tables_number      60

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2+x,1/2-y,1/2-z
3 -x,1/2-y,1/2+z
4 1/2-x,y,-z
5 -x,-y,-z
6 1/2-x,1/2+y,1/2+z
7 x,1/2+y,1/2-z
8 1/2+x,-y,z

_cell_length_a                   7.1905(10)
_cell_length_b                   11.4643(15)
_cell_length_c                   13.8150(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1138.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    11427
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_min  0.8831
_exptl_absorpt_correction_T_max  0.8831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11427
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1246
_reflns_number_gt                1203
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

_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 > 2σ(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)+(0.0000P)²+4.9990P] 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         1246
_refine_ls_number_parameters     67
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1696
_refine_ls_wR_factor_gt          0.1692
_refine_ls_goodness_of_fit_ref   1.292
_refine_ls_restrained_S_all      1.300
_refine_ls_shift/su_max          0.010
_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
C1 C 0.0568(5) 0.3803(3) 0.2716(3) 0.0184(7) Uani 1 1 d D . .
C2 C 0.1219(5) 0.2799(3) 0.2265(3) 0.0246(8) Uani 1 1 d D . .
H2 H 0.1864 0.2240 0.2619 0.030 Uiso 1 1 calc R . .
C3 C 0.0901(6) 0.2637(3) 0.1287(3) 0.0299(9) Uani 1 1 d . . .
H3 H 0.1370 0.1979 0.0978 0.036 Uiso 1 1 calc R . .
C6 C -0.0431(5) 0.4623(3) 0.2191(3) 0.0201(7) Uani 1 1 d . . .
H6 H -0.0871 0.5293 0.2493 0.024 Uiso 1 1 calc R . .
C5 C -0.0767(6) 0.4439(3) 0.1223(3) 0.0262(9) Uani 1 1 d . . .
H5 H -0.1442 0.4987 0.0872 0.031 Uiso 1 1 calc R . .
C4 C -0.0111(6) 0.3447(4) 0.0764(3) 0.0301(9) Uani 1 1 d . . .
H4 H -0.0348 0.3326 0.0110 0.036 Uiso 1 1 calc R . .
S1 S 0.09981(15) 0.40337(9) 0.39665(7) 0.0287(3) Uani 1 1 d D . .
H1 H 0.251(4) 0.461(3) 0.419(2) 0.034 Uiso 1 1 d D . .

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
C1 0.0171(17) 0.0200(16) 0.0181(17) 0.0032(13) 0.0002(13) -0.0036(13)
C2 0.0258(19) 0.0165(16) 0.032(2) 0.0024(14) -0.0011(16) 0.0013(14)
C3 0.036(2) 0.0211(18) 0.033(2) -0.0084(16) 0.0083(18) -0.0054(17)
C6 0.0186(17) 0.0158(15) 0.0258(18) 0.0027(13) 0.0019(14) 0.0011(14)
C5 0.025(2) 0.0262(18) 0.0271(19) 0.0109(16) -0.0089(16) -0.0048(16)
C4 0.039(2) 0.035(2) 0.0163(17) -0.0020(16) -0.0008(17) -0.0143(18)
S1 0.0366(6) 0.0327(6) 0.0168(5) 0.0019(4) -0.0033(4) -0.0027(4)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.387(5) . ?
C1 C2 1.390(5) . ?
C1 S1 1.774(4) . ?
C2 C3 1.384(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C6 C5 1.376(6) . ?
C6 H6 0.9300 . ?
C5 C4 1.385(6) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
S1 H1 1.314(18) . ?

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
C6 C1 C2 120.0(3) . . ?
C6 C1 S1 119.9(3) . . ?
C2 C1 S1 120.1(3) . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C1 S1 H1 116.8(16) . . ?

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
C6 C1 C2 C3 1.5(6) . . . . ?
S1 C1 C2 C3 -179.0(3) . . . . ?
C1 C2 C3 C4 -2.2(6) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
S1 C1 C6 C5 -179.8(3) . . . . ?
C1 C6 C5 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 1.6(6) . . . . ?
C6 C5 C4 C3 -0.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.097

#===END
####################################################################### 
# 
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1412309'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;
#==============================================================================

# 0. AUDIT DETAILS

_audit_creation_date             'Jul 10 21:49:05 2015'
_audit_creation_method           'PLATON <TABLE ACC> option'

_chemical_name_systematic        
;
 thiophenol-selenophenol
;
_chemical_name_common            'thiophenol-selenophenol alloy'
_chemical_melting_point          ?
_chemical_formula_moiety         '(C6 H6 S)0.57, (C6 H6 Se)0.43'
_chemical_formula_sum            'C6 H6 S0.57 Se0.43'
_chemical_formula_weight         130.34
_chemical_compound_source        'see text'

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'
S S 0.1246 0.1234 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2n'
_symmetry_space_group_name_H-M   'P n a b'
_symmetry_Int_Tables_number      60

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2+x,1/2-y,1/2-z
3 -x,1/2-y,1/2+z
4 1/2-x,y,-z
5 -x,-y,-z
6 1/2-x,1/2+y,1/2+z
7 x,1/2+y,1/2-z
8 1/2+x,-y,z

_cell_length_a                   7.2621(18)
_cell_length_b                   11.371(3)
_cell_length_c                   14.155(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1168.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    13527
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.99

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             526
_exptl_absorpt_coefficient_mu    2.938
_exptl_absorpt_correction_T_min  0.4727
_exptl_absorpt_correction_T_max  0.4727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            13527
_diffrn_reflns_av_R_equivalents  0.2067
_diffrn_reflns_av_sigmaI/netI    0.1234
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1140
_reflns_number_gt                618
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       
'Locally modified CAD4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'PLATON (Spek, 2003)'

_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 > 2σ(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)+(0.0000P)²+6.4217P] 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         1140
_refine_ls_number_parameters     70
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.084
_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
C6 C 0.6182(11) 0.2796(6) 0.7772(5) 0.037(2) Uani 1 1 d . . .
H6 H 0.6835 0.2227 0.7441 0.045 Uiso 1 1 calc R . .
C4 C 0.4878(13) 0.3496(7) 0.9223(6) 0.046(2) Uani 1 1 d . . .
H4 H 0.4660 0.3396 0.9865 0.056 Uiso 1 1 calc R . .
C5 C 0.5869(12) 0.2657(6) 0.8722(5) 0.045(2) Uani 1 1 d . . .
H5 H 0.6324 0.1998 0.9032 0.055 Uiso 1 1 calc R . .
C1 C 0.5525(11) 0.3784(6) 0.7306(5) 0.0316(19) Uani 1 1 d . . .
C3 C 0.4220(12) 0.4475(6) 0.8761(5) 0.044(2) Uani 1 1 d . . .
H3 H 0.3536 0.5033 0.9088 0.053 Uiso 1 1 calc R . .
C2 C 0.4576(10) 0.4623(6) 0.7817(5) 0.0303(19) Uani 1 1 d . . .
H2 H 0.4172 0.5302 0.7515 0.036 Uiso 1 1 calc R . .
S1 S 0.599(5) 0.3849(19) 0.604(3) 0.0370(14) Uani 0.57 1 d PD . .
Se1 Se 0.595(3) 0.4064(9) 0.6033(15) 0.0370(14) Uani 0.43 1 d PD . .
H1 H 0.762(6) 0.454(5) 0.584(4) 0.044 Uiso 1 1 d D . .

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
C6 0.036(6) 0.022(4) 0.054(5) -0.008(3) 0.004(4) -0.005(4)
C4 0.055(6) 0.042(5) 0.042(5) -0.005(4) 0.002(4) -0.009(5)
C5 0.048(6) 0.031(4) 0.057(5) 0.009(4) -0.002(5) -0.011(5)
C1 0.028(5) 0.027(4) 0.040(4) -0.001(3) -0.002(3) -0.007(3)
C3 0.040(6) 0.035(4) 0.057(5) -0.011(4) 0.015(5) -0.007(4)
C2 0.022(5) 0.023(4) 0.046(5) 0.001(3) 0.000(4) -0.004(3)
S1 0.0473(11) 0.032(4) 0.0317(6) -0.003(4) 0.0018(8) -0.001(3)
Se1 0.0473(11) 0.032(4) 0.0317(6) -0.003(4) 0.0018(8) -0.001(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C6 C5 1.372(10) . ?
C6 C1 1.387(9) . ?
C4 C3 1.377(10) . ?
C4 C5 1.389(11) . ?
C1 C2 1.381(9) . ?
C1 S1 1.83(4) . ?
C1 Se1 1.86(2) . ?
C3 C2 1.371(10) . ?

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
C5 C6 C1 120.2(7) . . ?
C3 C4 C5 119.5(7) . . ?
C6 C5 C4 120.4(7) . . ?
C2 C1 C6 118.8(7) . . ?
C2 C1 S1 125.4(10) . . ?
C6 C1 S1 115.8(10) . . ?
C2 C1 Se1 118.2(6) . . ?
C6 C1 Se1 122.9(7) . . ?
S1 C1 Se1 7.6(10) . . ?
C2 C3 C4 119.8(7) . . ?
C3 C2 C1 121.2(7) . . ?

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
C1 C6 C5 C4 0.7(12) . . . . ?
C3 C4 C5 C6 -0.5(13) . . . . ?
C5 C6 C1 C2 0.7(11) . . . . ?
C5 C6 C1 S1 -178.8(13) . . . . ?
C5 C6 C1 Se1 177.9(9) . . . . ?
C5 C4 C3 C2 -1.1(12) . . . . ?
C4 C3 C2 C1 2.6(12) . . . . ?
C6 C1 C2 C3 -2.4(11) . . . . ?
S1 C1 C2 C3 177.1(14) . . . . ?
Se1 C1 C2 C3 -179.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.105

#===END
