# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003
data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Prof Rolf Gleiter'
_publ_contact_author_address     
;
Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
D-69120 Heidelberg
Germany
;
_publ_contact_author_phone       '049 6221 54- 8400'
_publ_contact_author_fax         '049 6221 54- 4205'
_publ_contact_author_email       rolf.gleiter@urz.uni-heidelberg.de
_publ_requested_coeditor_name    ?

_publ_contact_letter             
;
paper to be submitted for publication in Organic and Biomolecular Chemistry
;

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

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Syntheses and Solid State Structures of Cyclic Diynes with Two Chalcogen
Centers A Competition Between Weak Interactions
;

loop_
_publ_author_name
_publ_author_address
H.J.Schulte
;
Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
69120 Heidelberg
Bundesrepublik Deutschland
;
D.B.Werz
;
Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
69120 Heidelberg
Bundesrepublik Deutschland
;
F.Rominger
;
Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
69120 Heidelberg
Bundesrepublik Deutschland
;
R.Gleiter
;
Organisch-Chemisches Institut
Universitat Heidelberg
Im Neuenheimer Feld 270
69120 Heidelberg
Bundesrepublik Deutschland
;

#===END

data_hse22_(in_paper_4S23)
_database_code_CSD               207497

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 S2'
_chemical_formula_weight         210.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.5954(2)
_cell_length_b                   9.59610(10)
_cell_length_c                   9.1230(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.3180(10)
_cell_angle_gamma                90.00
_cell_volume                     1129.90(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8418
_exptl_absorpt_correction_T_max  0.9628
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11416
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2592
_reflns_number_gt                2062
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.6157P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2592
_refine_ls_number_parameters     150
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.003

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
C2 C 0.85365(16) 0.7671(2) 0.0914(2) 0.0460(5) Uani 1 1 d D A .
C3 C 0.79796(16) 0.8508(2) 0.1206(2) 0.0454(5) Uani 1 1 d D . .
C4 C 0.72905(18) 0.9465(2) 0.1653(3) 0.0543(5) Uani 1 1 d . . .
H4A H 0.6916 1.0046 0.0754 0.065 Uiso 1 1 calc R . .
H4B H 0.7706 1.0092 0.2477 0.065 Uiso 1 1 calc R . .
C5 C 0.65066(16) 0.8676(2) 0.2232(2) 0.0474(5) Uani 1 1 d . . .
H5A H 0.6879 0.7980 0.3010 0.057 Uiso 1 1 calc R . .
H5B H 0.6166 0.9341 0.2747 0.057 Uiso 1 1 calc R . .
C6 C 0.56797(16) 0.7935(2) 0.0940(2) 0.0489(5) Uani 1 1 d . . .
H6A H 0.5157 0.8626 0.0375 0.059 Uiso 1 1 calc R . .
H6B H 0.6006 0.7539 0.0204 0.059 Uiso 1 1 calc R . .
C7 C 0.51349(15) 0.6771(2) 0.1520(2) 0.0494(5) Uani 1 1 d . . .
H7A H 0.4913 0.7121 0.2388 0.059 Uiso 1 1 calc R . .
H7B H 0.4507 0.6482 0.0681 0.059 Uiso 1 1 calc R . .
C8 C 0.58145(15) 0.5564(2) 0.2037(2) 0.0475(5) Uani 1 1 d D A .
C9 C 0.63919(16) 0.4606(2) 0.2377(3) 0.0519(5) Uani 1 1 d DU . .
S2 S 0.7224(2) 0.3233(3) 0.2835(4) 0.0885(10) Uani 0.706(6) 1 d PDU A 1
C11 C 0.8209(3) 0.3831(4) 0.1958(4) 0.0528(10) Uani 0.706(6) 1 d PDU A 1
H11A H 0.8665 0.3044 0.1892 0.063 Uiso 0.706(6) 1 calc PR A 1
H11B H 0.7864 0.4182 0.0900 0.063 Uiso 0.706(6) 1 calc PR A 1
C12 C 0.8854(2) 0.4994(3) 0.2960(3) 0.0436(8) Uani 0.706(6) 1 d PDU A 1
H12A H 0.8387 0.5771 0.3012 0.052 Uiso 0.706(6) 1 calc PR A 1
H12B H 0.9172 0.4636 0.4022 0.052 Uiso 0.706(6) 1 calc PR A 1
C13 C 0.9700(3) 0.5547(5) 0.2370(5) 0.0477(9) Uani 0.706(6) 1 d PDU A 1
H13A H 1.0141 0.4751 0.2284 0.057 Uiso 0.706(6) 1 calc PR A 1
H13B H 1.0137 0.6183 0.3164 0.057 Uiso 0.706(6) 1 calc PR A 1
S1 S 0.93282(5) 0.64554(7) 0.05609(7) 0.0609(2) Uani 1 1 d DU . .
S2B S 0.7110(4) 0.3166(6) 0.2736(7) 0.0587(15) Uani 0.294(6) 1 d PDU A 2
C11B C 0.8385(6) 0.3886(9) 0.3293(11) 0.065(3) Uani 0.294(6) 1 d PDU A 2
H11C H 0.8484 0.4569 0.4140 0.078 Uiso 0.294(6) 1 calc PR A 2
H11D H 0.8917 0.3147 0.3627 0.078 Uiso 0.294(6) 1 calc PR A 2
C12B C 0.8433(7) 0.4592(11) 0.1819(13) 0.070(3) Uani 0.294(6) 1 d PDU A 2
H12C H 0.8334 0.3893 0.0987 0.085 Uiso 0.294(6) 1 calc PR A 2
H12D H 0.7875 0.5296 0.1477 0.085 Uiso 0.294(6) 1 calc PR A 2
C13B C 0.9445(9) 0.5263(14) 0.2136(15) 0.067(5) Uiso 0.294(6) 1 d PDU A 2
H13C H 0.9988 0.4559 0.2190 0.081 Uiso 0.294(6) 1 calc PR A 2
H13D H 0.9630 0.5772 0.3130 0.081 Uiso 0.294(6) 1 calc PR A 2

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
C2 0.0482(11) 0.0450(11) 0.0443(11) 0.0004(9) 0.0138(9) -0.0058(9)
C3 0.0500(11) 0.0394(10) 0.0447(11) 0.0045(8) 0.0117(9) -0.0069(9)
C4 0.0650(14) 0.0331(10) 0.0624(13) 0.0037(9) 0.0165(11) 0.0058(9)
C5 0.0510(11) 0.0446(11) 0.0453(10) -0.0021(9) 0.0135(9) 0.0107(9)
C6 0.0464(11) 0.0562(12) 0.0403(10) 0.0043(9) 0.0083(8) 0.0139(9)
C7 0.0363(10) 0.0593(13) 0.0496(11) -0.0060(9) 0.0092(8) 0.0067(9)
C8 0.0396(10) 0.0487(11) 0.0547(12) -0.0081(9) 0.0157(9) -0.0042(9)
C9 0.0461(11) 0.0414(11) 0.0699(14) -0.0063(10) 0.0206(10) -0.0038(9)
S2 0.0834(16) 0.0385(10) 0.161(3) 0.0222(12) 0.0632(15) 0.0124(9)
C11 0.0485(18) 0.048(2) 0.063(2) -0.0060(17) 0.0202(16) 0.0103(16)
C12 0.0427(15) 0.0470(16) 0.0372(16) 0.0008(12) 0.0068(12) 0.0044(12)
C13 0.0365(18) 0.053(2) 0.0505(19) -0.0016(16) 0.0091(15) 0.0058(17)
S1 0.0671(4) 0.0677(4) 0.0576(4) 0.0008(3) 0.0335(3) 0.0099(3)
S2B 0.0330(15) 0.0307(19) 0.095(3) -0.0201(18) -0.0053(16) -0.0017(12)
C11B 0.060(4) 0.057(5) 0.078(7) 0.007(4) 0.020(4) 0.018(4)
C12B 0.058(6) 0.061(6) 0.097(9) 0.025(6) 0.031(6) 0.020(5)

_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
C2 C3 1.190(3) . ?
C2 S1 1.685(2) . ?
C3 C4 1.458(3) . ?
C4 C5 1.530(3) . ?
C5 C6 1.525(3) . ?
C6 C7 1.524(3) . ?
C7 C8 1.464(3) . ?
C8 C9 1.185(3) . ?
C9 S2B 1.664(6) . ?
C9 S2 1.701(3) . ?
S2 C11 1.854(5) . ?
C11 C12 1.531(5) . ?
C12 C13 1.512(5) . ?
C13 S1 1.793(4) . ?
S1 C13B 1.804(11) . ?
S2B C11B 1.785(9) . ?
C11B C12B 1.525(11) . ?
C12B C13B 1.464(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 S1 177.97(19) . . ?
C2 C3 C4 175.7(2) . . ?
C3 C4 C5 111.31(17) . . ?
C6 C5 C4 112.82(18) . . ?
C7 C6 C5 113.21(17) . . ?
C8 C7 C6 111.43(17) . . ?
C9 C8 C7 175.5(2) . . ?
C8 C9 S2B 174.3(2) . . ?
C8 C9 S2 179.0(3) . . ?
S2B C9 S2 5.5(2) . . ?
C9 S2 C11 99.74(19) . . ?
C12 C11 S2 108.9(2) . . ?
C13 C12 C11 113.6(3) . . ?
C12 C13 S1 118.2(3) . . ?
C2 S1 C13 99.92(15) . . ?
C2 S1 C13B 100.8(5) . . ?
C13 S1 C13B 14.0(4) . . ?
C9 S2B C11B 101.1(4) . . ?
C12B C11B S2B 103.1(7) . . ?
C13B C12B C11B 108.6(9) . . ?
C12B C13B S1 106.2(8) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.042

#===END

data_hse15_(in_paper_5S22)
_database_code_CSD               207498

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 S2'
_chemical_formula_weight         210.34

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I-4

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

_cell_length_a                   20.0210(17)
_cell_length_b                   20.0210(17)
_cell_length_c                   5.6850(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2278.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .44
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3482
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2261
_reflns_number_gt                1655
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.5764P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(12)
_refine_ls_number_reflns         2261
_refine_ls_number_parameters     155
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
S1 S -0.00374(3) 0.40508(3) -0.98112(15) 0.0464(2) Uani 1 1 d . . .
S2 S 0.06410(4) 0.25998(4) -1.51874(17) 0.0597(3) Uani 1 1 d . . .
C1 C 0.04721(14) 0.34368(15) -1.1362(5) 0.0440(7) Uani 1 1 d . . .
H1A H 0.0931 0.3613 -1.1550 0.053 Uiso 1 1 calc R . .
H1B H 0.0498 0.3023 -1.0414 0.053 Uiso 1 1 calc R . .
C2 C 0.01897(15) 0.32756(14) -1.3733(5) 0.0476(7) Uani 1 1 d . . .
H2A H 0.0208 0.3680 -1.4734 0.057 Uiso 1 1 calc R . .
H2B H -0.0285 0.3146 -1.3557 0.057 Uiso 1 1 calc R . .
C4 C 0.02185(17) 0.19426(17) -1.4046(6) 0.0554(9) Uani 1 1 d D . .
C5 C -0.00971(19) 0.14934(18) -1.3248(7) 0.0655(10) Uani 1 1 d D A .
C6 C -0.0537(2) 0.09846(18) -1.2232(9) 0.0855(13) Uani 1 1 d DU . .
H6A H -0.0302 0.0761 -1.0917 0.103 Uiso 0.734(8) 1 calc PR A 1
H6B H -0.0636 0.0643 -1.3440 0.103 Uiso 0.734(8) 1 calc PR A 1
H6C H -0.0270 0.0584 -1.1838 0.103 Uiso 0.266(8) 1 calc PR A 2
H6D H -0.0875 0.0853 -1.3416 0.103 Uiso 0.266(8) 1 calc PR A 2
C7 C -0.1179(3) 0.1272(3) -1.1346(12) 0.0693(19) Uani 0.734(8) 1 d PDU A 1
H7A H -0.1472 0.0905 -1.0804 0.083 Uiso 0.734(8) 1 calc PR A 1
H7B H -0.1409 0.1505 -1.2649 0.083 Uiso 0.734(8) 1 calc PR A 1
C8 C -0.1067(5) 0.1756(5) -0.9344(13) 0.076(2) Uani 0.734(8) 1 d PDU A 1
H8A H -0.0692 0.2059 -0.9735 0.091 Uiso 0.734(8) 1 calc PR A 1
H8B H -0.0947 0.1506 -0.7901 0.091 Uiso 0.734(8) 1 calc PR A 1
C9 C -0.1718(3) 0.2175(3) -0.8895(14) 0.082(2) Uani 0.734(8) 1 d PDU A 1
H9A H -0.1878 0.2364 -1.0403 0.099 Uiso 0.734(8) 1 calc PR A 1
H9B H -0.2072 0.1879 -0.8271 0.099 Uiso 0.734(8) 1 calc PR A 1
C10 C -0.1596(4) 0.2732(3) -0.7183(12) 0.077(2) Uani 0.734(8) 1 d PDU A 1
H10A H -0.2020 0.2966 -0.6829 0.092 Uiso 0.734(8) 1 calc PR A 1
H10B H -0.1413 0.2551 -0.5695 0.092 Uiso 0.734(8) 1 calc PR A 1
C11 C -0.11088(18) 0.32066(17) -0.8262(7) 0.0708(11) Uani 1 1 d DU . .
C12 C -0.06769(15) 0.35525(15) -0.8961(5) 0.0484(8) Uani 1 1 d D A .
C7B C -0.0881(15) 0.1223(10) -1.009(5) 0.194(17) Uani 0.266(8) 1 d PDU A 2
H7B1 H -0.0539 0.1307 -0.8867 0.233 Uiso 0.266(8) 1 calc PR A 2
H7B2 H -0.1173 0.0860 -0.9512 0.233 Uiso 0.266(8) 1 calc PR A 2
C8B C -0.1293(16) 0.1836(13) -1.034(4) 0.135(12) Uani 0.266(8) 1 d PDU A 2
H8B1 H -0.1704 0.1745 -1.1258 0.163 Uiso 0.266(8) 1 calc PR A 2
H8B2 H -0.1038 0.2197 -1.1131 0.163 Uiso 0.266(8) 1 calc PR A 2
C9B C -0.1464(7) 0.2030(6) -0.773(3) 0.066(5) Uani 0.266(8) 1 d PDU A 2
H9B1 H -0.1819 0.1746 -0.7038 0.079 Uiso 0.266(8) 1 calc PR A 2
H9B2 H -0.1067 0.2033 -0.6689 0.079 Uiso 0.266(8) 1 calc PR A 2
C10B C -0.1711(7) 0.2740(7) -0.836(4) 0.080(7) Uani 0.266(8) 1 d PDU A 2
H10C H -0.1908 0.2742 -0.9957 0.095 Uiso 0.266(8) 1 calc PR A 2
H10D H -0.2056 0.2888 -0.7226 0.095 Uiso 0.266(8) 1 calc PR A 2

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
S1 0.0477(4) 0.0421(4) 0.0496(4) -0.0015(4) 0.0010(4) -0.0063(3)
S2 0.0689(5) 0.0603(5) 0.0498(5) -0.0018(5) 0.0104(5) 0.0107(4)
C1 0.0400(15) 0.0504(17) 0.0417(16) 0.0044(15) -0.0041(14) -0.0017(14)
C2 0.0506(17) 0.0454(17) 0.0468(17) 0.0063(15) -0.0029(15) 0.0047(15)
C4 0.063(2) 0.0512(19) 0.052(2) -0.0101(17) -0.0148(17) 0.0130(17)
C5 0.074(2) 0.0454(19) 0.077(3) -0.0047(19) -0.017(2) 0.004(2)
C6 0.098(3) 0.052(2) 0.107(3) 0.000(2) -0.032(3) -0.017(2)
C7 0.071(4) 0.057(4) 0.080(4) 0.016(3) -0.025(3) -0.020(3)
C8 0.072(4) 0.071(4) 0.086(5) 0.004(4) 0.000(4) -0.027(3)
C9 0.065(4) 0.088(5) 0.094(5) 0.013(4) 0.007(4) -0.035(3)
C10 0.072(4) 0.086(5) 0.073(5) 0.022(3) 0.012(4) -0.013(3)
C11 0.053(2) 0.054(2) 0.105(3) 0.011(2) 0.020(2) -0.0017(18)
C12 0.0503(18) 0.0444(17) 0.0505(19) 0.0031(15) 0.0032(15) 0.0052(16)
C7B 0.24(3) 0.100(15) 0.25(4) 0.046(19) 0.18(3) -0.032(18)
C8B 0.14(3) 0.093(16) 0.17(2) -0.036(19) 0.07(2) -0.070(12)
C9B 0.033(8) 0.067(8) 0.097(11) 0.052(8) -0.016(7) -0.011(6)
C10B 0.049(9) 0.063(9) 0.127(19) 0.062(10) 0.022(11) 0.000(6)

_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
S1 C12 1.694(3) . ?
S1 C1 1.825(3) . ?
S2 C4 1.694(4) . ?
S2 C2 1.825(3) . ?
C1 C2 1.497(4) . ?
C4 C5 1.189(5) . ?
C5 C6 1.465(5) . ?
C6 C7B 1.478(15) . ?
C6 C7 1.495(7) . ?
C7 C8 1.511(8) . ?
C8 C9 1.573(9) . ?
C9 C10 1.500(8) . ?
C10 C11 1.493(7) . ?
C11 C12 1.177(4) . ?
C11 C10B 1.526(13) . ?
C7B C8B 1.486(17) . ?
C8B C9B 1.577(16) . ?
C9B C10B 1.548(14) . ?

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
C12 S1 C1 99.42(14) . . ?
C4 S2 C2 98.92(15) . . ?
C2 C1 S1 111.7(2) . . ?
C1 C2 S2 112.4(2) . . ?
C5 C4 S2 177.8(3) . . ?
C4 C5 C6 174.6(4) . . ?
C5 C6 C7B 112.3(9) . . ?
C5 C6 C7 112.5(4) . . ?
C7B C6 C7 36.6(14) . . ?
C6 C7 C8 111.9(5) . . ?
C7 C8 C9 110.0(6) . . ?
C10 C9 C8 111.5(6) . . ?
C11 C10 C9 108.3(5) . . ?
C12 C11 C10 173.1(5) . . ?
C12 C11 C10B 158.2(10) . . ?
C10 C11 C10B 27.1(8) . . ?
C11 C12 S1 176.8(3) . . ?
C6 C7B C8B 116.5(18) . . ?
C7B C8B C9B 103.4(16) . . ?
C10B C9B C8B 94.3(13) . . ?
C11 C10B C9B 107.5(11) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037

#===END

data_hse13_(in_paper_5S23)
_database_code_CSD               207499

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 S2'
_chemical_formula_weight         224.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   4.54020(10)
_cell_length_b                   13.4819(2)
_cell_length_c                   9.7130(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2740(10)
_cell_angle_gamma                90.00
_cell_volume                     590.98(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6006
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.45
_reflns_number_total             2671
_reflns_number_gt                2579
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.0529P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     128
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64860(7) 0.80367(3) 0.54770(4) 0.03212(10) Uani 1 1 d . . .
S2 S 0.55227(9) 0.49176(2) 0.16772(4) 0.03592(11) Uani 1 1 d . . .
C2 C 0.4826(3) 0.87472(11) 0.41846(15) 0.0260(3) Uani 1 1 d . . .
C3 C 0.3595(3) 0.92575(11) 0.32926(15) 0.0276(3) Uani 1 1 d . . .
C4 C 0.2075(4) 0.98692(12) 0.21712(17) 0.0345(4) Uani 1 1 d . . .
H4A H 0.3575 1.0209 0.1673 0.041 Uiso 1 1 calc R . .
H4B H 0.0881 1.0384 0.2579 0.041 Uiso 1 1 calc R . .
C5 C 0.0029(4) 0.92414(11) 0.11294(16) 0.0316(3) Uani 1 1 d . . .
H5A H -0.1475 0.8907 0.1632 0.038 Uiso 1 1 calc R . .
H5B H -0.1030 0.9690 0.0435 0.038 Uiso 1 1 calc R . .
C6 C 0.1680(3) 0.84622(10) 0.03807(15) 0.0247(3) Uani 1 1 d . . .
H6A H 0.3119 0.8798 -0.0158 0.030 Uiso 1 1 calc R . .
H6B H 0.2811 0.8032 0.1076 0.030 Uiso 1 1 calc R . .
C7 C -0.0361(3) 0.78192(11) -0.05924(15) 0.0276(3) Uani 1 1 d . . .
H7A H -0.1465 0.8250 -0.1296 0.033 Uiso 1 1 calc R . .
H7B H -0.1825 0.7495 -0.0056 0.033 Uiso 1 1 calc R . .
C8 C 0.1288(4) 0.70098(11) -0.13417(15) 0.0292(3) Uani 1 1 d . . .
H8A H -0.0149 0.6647 -0.1998 0.035 Uiso 1 1 calc R . .
H8B H 0.2759 0.7328 -0.1881 0.035 Uiso 1 1 calc R . .
C9 C 0.2812(3) 0.63028(11) -0.03445(15) 0.0284(3) Uani 1 1 d . . .
C10 C 0.4003(3) 0.57432(11) 0.04997(15) 0.0273(3) Uani 1 1 d . . .
C12 C 0.7927(3) 0.57166(12) 0.28159(16) 0.0309(3) Uani 1 1 d . . .
H12A H 0.9061 0.5303 0.3531 0.037 Uiso 1 1 calc R . .
H12B H 0.9367 0.6044 0.2268 0.037 Uiso 1 1 calc R . .
C13 C 0.6256(3) 0.65060(11) 0.35254(15) 0.0229(3) Uani 1 1 d . . .
H13A H 0.4785 0.6186 0.4062 0.027 Uiso 1 1 calc R . .
H13B H 0.5174 0.6939 0.2818 0.027 Uiso 1 1 calc R . .
C14 C 0.8378(3) 0.71317(11) 0.44926(16) 0.0269(3) Uani 1 1 d . . .
H14A H 0.9755 0.7485 0.3939 0.032 Uiso 1 1 calc R . .
H14B H 0.9572 0.6687 0.5146 0.032 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
S1 0.0451(2) 0.02915(19) 0.02051(16) -0.00303(14) -0.00348(13) 0.00200(15)
S2 0.0533(2) 0.02263(17) 0.02978(18) -0.00383(16) -0.00442(16) 0.00795(18)
C2 0.0318(8) 0.0228(7) 0.0234(6) -0.0049(5) 0.0025(6) -0.0018(5)
C3 0.0343(8) 0.0238(6) 0.0251(7) -0.0053(5) 0.0050(6) 0.0001(6)
C4 0.0489(10) 0.0270(7) 0.0267(7) 0.0017(6) 0.0001(7) 0.0130(7)
C5 0.0324(7) 0.0326(8) 0.0288(7) 0.0027(6) -0.0007(6) 0.0105(6)
C6 0.0240(7) 0.0252(6) 0.0240(7) 0.0010(5) -0.0009(5) 0.0015(5)
C7 0.0254(7) 0.0279(7) 0.0275(7) 0.0055(6) -0.0060(6) -0.0029(6)
C8 0.0394(9) 0.0253(7) 0.0206(7) 0.0003(5) -0.0067(6) -0.0058(6)
C9 0.0353(8) 0.0252(7) 0.0238(7) -0.0066(5) -0.0004(6) -0.0070(6)
C10 0.0353(8) 0.0249(7) 0.0215(6) -0.0054(5) 0.0020(6) -0.0011(6)
C12 0.0312(8) 0.0312(8) 0.0288(7) -0.0036(6) -0.0032(6) 0.0094(6)
C13 0.0246(7) 0.0225(6) 0.0207(6) -0.0001(5) -0.0015(5) 0.0017(5)
C14 0.0266(7) 0.0272(7) 0.0261(7) 0.0002(5) -0.0014(6) 0.0013(6)

_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
S1 C2 1.6896(15) . ?
S1 C14 1.8221(15) . ?
S2 C10 1.6884(15) . ?
S2 C12 1.8199(16) . ?
C2 C3 1.196(2) . ?
C3 C4 1.476(2) . ?
C4 C5 1.549(2) . ?
C5 C6 1.521(2) . ?
C6 C7 1.5206(19) . ?
C7 C8 1.549(2) . ?
C8 C9 1.476(2) . ?
C9 C10 1.199(2) . ?
C12 C13 1.516(2) . ?
C13 C14 1.525(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
C2 S1 C14 100.80(7) . . ?
C10 S2 C12 101.25(7) . . ?
C3 C2 S1 178.24(13) . . ?
C2 C3 C4 178.78(15) . . ?
C3 C4 C5 112.06(12) . . ?
C6 C5 C4 113.45(13) . . ?
C7 C6 C5 113.09(12) . . ?
C6 C7 C8 113.61(12) . . ?
C9 C8 C7 111.25(12) . . ?
C10 C9 C8 177.82(15) . . ?
C9 C10 S2 177.02(14) . . ?
C13 C12 S2 113.27(10) . . ?
C12 C13 C14 110.77(12) . . ?
C13 C14 S1 113.04(10) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.034

#===END

data_hse21_(in_paper_5S24)
_database_code_CSD               207500

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 S2'
_chemical_formula_weight         238.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   18.2162(2)
_cell_length_b                   9.07480(10)
_cell_length_c                   16.3181(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1770(10)
_cell_angle_gamma                90.00
_cell_volume                     2626.49(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8836
_exptl_absorpt_correction_T_max  0.9393
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20189
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         24.08
_reflns_number_total             4164
_reflns_number_gt                3200
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.7657P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4164
_refine_ls_number_parameters     290
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.004

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
S1_1 S 0.17298(4) 1.14989(7) -0.19402(4) 0.03991(19) Uani 1 1 d . A .
S2_1 S 0.26299(4) 1.13321(7) 0.16763(4) 0.0401(2) Uani 1 1 d . A .
C2_1 C 0.10276(14) 1.0440(3) -0.17376(15) 0.0355(6) Uani 1 1 d . . .
C3_1 C 0.05689(15) 0.9547(3) -0.16561(16) 0.0411(6) Uani 1 1 d . . .
C4_1 C 0.00149(15) 0.8420(3) -0.15560(19) 0.0506(7) Uani 1 1 d . . .
H4A_1 H -0.0147 0.7877 -0.2093 0.061 Uiso 1 1 calc R . .
H4B_1 H -0.0434 0.8918 -0.1441 0.061 Uiso 1 1 calc R . .
C5_1 C 0.03073(15) 0.7314(3) -0.08540(18) 0.0481(7) Uani 1 1 d . . .
H5A_1 H -0.0083 0.6554 -0.0859 0.058 Uiso 1 1 calc R . .
H5B_1 H 0.0758 0.6815 -0.0965 0.058 Uiso 1 1 calc R . .
C6_1 C 0.05122(15) 0.8021(3) 0.00111(17) 0.0435(7) Uani 1 1 d . . .
H6A_1 H 0.0883 0.8816 0.0005 0.052 Uiso 1 1 calc R . .
H6B_1 H 0.0055 0.8478 0.0132 0.052 Uiso 1 1 calc R . .
C7_1 C 0.08400(16) 0.6948(3) 0.07126(19) 0.0500(7) Uani 1 1 d . . .
H7A_1 H 0.1292 0.6477 0.0588 0.060 Uiso 1 1 calc R . .
H7B_1 H 0.0465 0.6165 0.0728 0.060 Uiso 1 1 calc R . .
C8_1 C 0.10577(17) 0.7681(3) 0.15760(19) 0.0546(8) Uani 1 1 d . . .
H8A_1 H 0.0596 0.8054 0.1728 0.065 Uiso 1 1 calc R . .
H8B_1 H 0.1285 0.6932 0.1999 0.065 Uiso 1 1 calc R . .
C9_1 C 0.15926(15) 0.8910(3) 0.16133(16) 0.0410(6) Uani 1 1 d . . .
C10_1 C 0.20094(14) 0.9926(3) 0.16133(15) 0.0364(6) Uani 1 1 d . . .
C12_1 C 0.20666(15) 1.2654(3) 0.09587(15) 0.0386(6) Uani 1 1 d DU . .
H12A_1 H 0.1538 1.2610 0.1017 0.046 Uiso 0.879(6) 1 calc PR A 1
H12B_1 H 0.2259 1.3661 0.1113 0.046 Uiso 0.879(6) 1 calc PR A 1
H12C_1 H 0.1722 1.3075 0.1287 0.046 Uiso 0.121(6) 1 calc PR A 2
H12D_1 H 0.2427 1.3452 0.0918 0.046 Uiso 0.121(6) 1 calc PR A 2
C13_1 C 0.2088(2) 1.2349(3) 0.00437(17) 0.0395(9) Uani 0.879(6) 1 d PDU A 1
H13A_1 H 0.2596 1.2586 -0.0041 0.047 Uiso 0.879(6) 1 calc PR A 1
H13B_1 H 0.1994 1.1288 -0.0078 0.047 Uiso 0.879(6) 1 calc PR A 1
C14_1 C 0.1506(2) 1.3248(3) -0.05624(18) 0.0385(9) Uani 0.879(6) 1 d PDU A 1
H14A_1 H 0.1524 1.4275 -0.0355 0.046 Uiso 0.879(6) 1 calc PR A 1
H14B_1 H 0.0999 1.2850 -0.0566 0.046 Uiso 0.879(6) 1 calc PR A 1
C15_1 C 0.16120(16) 1.3262(3) -0.14582(15) 0.0433(7) Uani 1 1 d DU . .
H15A_1 H 0.2060 1.3874 -0.1469 0.052 Uiso 0.879(6) 1 calc PR A 1
H15B_1 H 0.1170 1.3761 -0.1816 0.052 Uiso 0.879(6) 1 calc PR A 1
H15C_1 H 0.1833 1.4062 -0.1737 0.052 Uiso 0.121(6) 1 calc PR A 2
H15D_1 H 0.1070 1.3474 -0.1514 0.052 Uiso 0.121(6) 1 calc PR A 2
C13B_1 C 0.1573(12) 1.253(3) 0.0057(9) 0.037(6) Uani 0.121(6) 1 d PDU A 2
H13C_1 H 0.1448 1.1487 -0.0087 0.044 Uiso 0.121(6) 1 calc PR A 2
H13D_1 H 0.1097 1.3086 0.0009 0.044 Uiso 0.121(6) 1 calc PR A 2
C14B_1 C 0.2019(13) 1.316(2) -0.0521(9) 0.036(6) Uani 0.121(6) 1 d PDU A 2
H14C_1 H 0.2478 1.2557 -0.0476 0.043 Uiso 0.121(6) 1 calc PR A 2
H14D_1 H 0.2183 1.4165 -0.0321 0.043 Uiso 0.121(6) 1 calc PR A 2
S1_2 S 0.75704(4) 0.28522(7) 0.12053(4) 0.0440(2) Uani 1 1 d . . .
S2_2 S 0.65864(4) 0.45343(7) -0.23830(4) 0.03920(19) Uani 1 1 d . . .
C2_2 C 0.68243(14) 0.3902(3) 0.12881(14) 0.0328(6) Uani 1 1 d . . .
C3_2 C 0.63535(13) 0.4758(3) 0.13904(14) 0.0325(6) Uani 1 1 d . . .
C4_2 C 0.58004(14) 0.5855(3) 0.15132(15) 0.0365(6) Uani 1 1 d . . .
H4A_2 H 0.5915 0.6152 0.2113 0.044 Uiso 1 1 calc R . .
H4B_2 H 0.5293 0.5401 0.1381 0.044 Uiso 1 1 calc R . .
C5_2 C 0.57894(14) 0.7228(3) 0.09686(15) 0.0355(6) Uani 1 1 d . . .
H5A_2 H 0.5443 0.7965 0.1122 0.043 Uiso 1 1 calc R . .
H5B_2 H 0.6301 0.7665 0.1085 0.043 Uiso 1 1 calc R . .
C6_2 C 0.55400(14) 0.6890(2) 0.00375(14) 0.0325(6) Uani 1 1 d . . .
H6A_2 H 0.5020 0.6496 -0.0081 0.039 Uiso 1 1 calc R . .
H6B_2 H 0.5871 0.6114 -0.0107 0.039 Uiso 1 1 calc R . .
C7_2 C 0.55609(15) 0.8222(3) -0.05184(16) 0.0408(6) Uani 1 1 d . . .
H7A_2 H 0.6086 0.8585 -0.0422 0.049 Uiso 1 1 calc R . .
H7B_2 H 0.5251 0.9017 -0.0354 0.049 Uiso 1 1 calc R . .
C8_2 C 0.52723(15) 0.7893(3) -0.14521(16) 0.0433(7) Uani 1 1 d . . .
H8A_2 H 0.4741 0.7565 -0.1551 0.052 Uiso 1 1 calc R . .
H8B_2 H 0.5283 0.8813 -0.1775 0.052 Uiso 1 1 calc R . .
C9_2 C 0.57094(15) 0.6766(3) -0.17700(15) 0.0366(6) Uani 1 1 d . . .
C10_2 C 0.60729(14) 0.5831(3) -0.20149(15) 0.0351(6) Uani 1 1 d . . .
C12_2 C 0.64253(14) 0.2970(2) -0.17475(15) 0.0350(6) Uani 1 1 d . . .
H12A_2 H 0.5879 0.2903 -0.1766 0.042 Uiso 1 1 calc R . .
H12B_2 H 0.6574 0.2057 -0.1999 0.042 Uiso 1 1 calc R . .
C13_2 C 0.68543(14) 0.3054(3) -0.08330(15) 0.0348(6) Uani 1 1 d . . .
H13A_2 H 0.7400 0.2927 -0.0800 0.042 Uiso 1 1 calc R . .
H13B_2 H 0.6779 0.4038 -0.0603 0.042 Uiso 1 1 calc R . .
C14_2 C 0.65898(15) 0.1877(3) -0.03087(16) 0.0405(6) Uani 1 1 d . . .
H14A_2 H 0.6132 0.2243 -0.0145 0.049 Uiso 1 1 calc R . .
H14B_2 H 0.6443 0.0998 -0.0667 0.049 Uiso 1 1 calc R . .
C15_2 C 0.71508(17) 0.1401(3) 0.04813(16) 0.0472(7) Uani 1 1 d . . .
H15A_2 H 0.7563 0.0856 0.0311 0.057 Uiso 1 1 calc R . .
H15B_2 H 0.6895 0.0702 0.0790 0.057 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
S1_1 0.0441(4) 0.0412(4) 0.0343(4) 0.0006(3) 0.0088(3) -0.0001(3)
S2_1 0.0361(4) 0.0358(4) 0.0439(4) -0.0001(3) 0.0001(3) -0.0024(3)
C2_1 0.0381(14) 0.0352(14) 0.0292(13) -0.0044(11) -0.0008(11) 0.0051(12)
C3_1 0.0391(15) 0.0391(15) 0.0401(15) -0.0065(12) -0.0010(12) 0.0023(13)
C4_1 0.0391(15) 0.0448(16) 0.0615(19) -0.0064(14) -0.0017(13) -0.0100(13)
C5_1 0.0365(15) 0.0340(14) 0.070(2) -0.0055(14) 0.0046(14) -0.0105(12)
C6_1 0.0392(15) 0.0297(13) 0.0614(18) 0.0005(12) 0.0109(13) -0.0040(12)
C7_1 0.0412(16) 0.0322(14) 0.073(2) 0.0070(13) 0.0057(14) -0.0085(13)
C8_1 0.0565(18) 0.0462(17) 0.060(2) 0.0153(14) 0.0112(15) -0.0094(15)
C9_1 0.0425(15) 0.0366(15) 0.0419(16) 0.0067(12) 0.0056(12) 0.0019(13)
C10_1 0.0362(14) 0.0363(14) 0.0347(14) 0.0011(11) 0.0041(11) 0.0057(12)
C12_1 0.0489(16) 0.0301(13) 0.0317(14) 0.0010(11) -0.0016(12) 0.0002(12)
C13_1 0.041(2) 0.0423(18) 0.0323(17) -0.0003(14) 0.0023(14) 0.0100(16)
C14_1 0.040(2) 0.0323(17) 0.0398(19) 0.0005(13) 0.0026(15) 0.0066(16)
C15_1 0.0575(17) 0.0345(14) 0.0328(14) 0.0025(11) -0.0008(13) -0.0060(13)
C13B_1 0.041(15) 0.041(13) 0.026(7) -0.002(9) 0.003(8) -0.003(11)
C14B_1 0.057(17) 0.022(11) 0.026(7) 0.000(9) 0.005(9) -0.009(12)
S1_2 0.0395(4) 0.0412(4) 0.0451(4) -0.0050(3) -0.0033(3) 0.0103(3)
S2_2 0.0480(4) 0.0386(4) 0.0329(4) -0.0035(3) 0.0133(3) -0.0054(3)
C2_2 0.0378(14) 0.0311(13) 0.0269(13) -0.0011(10) 0.0020(11) -0.0045(12)
C3_2 0.0334(13) 0.0345(13) 0.0269(13) -0.0042(10) 0.0012(10) -0.0028(12)
C4_2 0.0350(14) 0.0438(14) 0.0300(14) -0.0068(11) 0.0059(11) 0.0019(12)
C5_2 0.0344(14) 0.0323(13) 0.0384(15) -0.0096(11) 0.0052(11) 0.0027(11)
C6_2 0.0330(13) 0.0277(12) 0.0358(14) -0.0033(10) 0.0061(11) -0.0016(11)
C7_2 0.0474(16) 0.0266(13) 0.0507(17) 0.0013(11) 0.0158(13) 0.0062(12)
C8_2 0.0474(16) 0.0398(15) 0.0439(16) 0.0167(12) 0.0129(13) 0.0123(13)
C9_2 0.0429(15) 0.0356(14) 0.0314(14) 0.0093(11) 0.0084(12) -0.0022(13)
C10_2 0.0402(14) 0.0343(14) 0.0287(13) 0.0058(11) 0.0037(11) -0.0078(12)
C12_2 0.0415(14) 0.0275(12) 0.0344(14) -0.0048(10) 0.0053(11) -0.0025(11)
C13_2 0.0357(14) 0.0312(13) 0.0359(14) -0.0036(11) 0.0048(11) -0.0022(11)
C14_2 0.0499(16) 0.0284(13) 0.0413(15) -0.0035(11) 0.0062(12) -0.0048(12)
C15_2 0.0706(19) 0.0279(13) 0.0402(15) -0.0017(11) 0.0067(14) 0.0100(13)

_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
S1_1 C2_1 1.692(3) . ?
S1_1 C15_1 1.817(3) . ?
S2_1 C10_1 1.692(3) . ?
S2_1 C12_1 1.821(2) . ?
C2_1 C3_1 1.193(3) . ?
C3_1 C4_1 1.472(4) . ?
C4_1 C5_1 1.525(4) . ?
C5_1 C6_1 1.518(4) . ?
C6_1 C7_1 1.517(4) . ?
C7_1 C8_1 1.526(4) . ?
C8_1 C9_1 1.473(4) . ?
C9_1 C10_1 1.194(3) . ?
C12_1 C13_1 1.528(4) . ?
C12_1 C13B_1 1.544(15) . ?
C13_1 C14_1 1.513(4) . ?
C14_1 C15_1 1.517(4) . ?
C15_1 C14B_1 1.543(15) . ?
C13B_1 C14B_1 1.492(18) . ?
S1_2 C2_2 1.690(3) . ?
S1_2 C15_2 1.817(3) . ?
S2_2 C10_2 1.696(3) . ?
S2_2 C12_2 1.821(2) . ?
C2_2 C3_2 1.197(3) . ?
C3_2 C4_2 1.463(3) . ?
C4_2 C5_2 1.528(3) . ?
C5_2 C6_2 1.515(3) . ?
C6_2 C7_2 1.517(3) . ?
C7_2 C8_2 1.524(4) . ?
C8_2 C9_2 1.462(4) . ?
C9_2 C10_2 1.199(3) . ?
C12_2 C13_2 1.521(3) . ?
C13_2 C14_2 1.514(3) . ?
C14_2 C15_2 1.514(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_1 S1_1 C15_1 104.26(12) . . ?
C10_1 S2_1 C12_1 100.78(12) . . ?
C3_1 C2_1 S1_1 171.0(2) . . ?
C2_1 C3_1 C4_1 178.7(3) . . ?
C3_1 C4_1 C5_1 114.2(2) . . ?
C6_1 C5_1 C4_1 113.0(2) . . ?
C7_1 C6_1 C5_1 113.7(2) . . ?
C6_1 C7_1 C8_1 113.1(2) . . ?
C9_1 C8_1 C7_1 113.5(2) . . ?
C10_1 C9_1 C8_1 177.4(3) . . ?
C9_1 C10_1 S2_1 176.3(2) . . ?
C13_1 C12_1 C13B_1 36.3(8) . . ?
C13_1 C12_1 S2_1 111.88(19) . . ?
C13B_1 C12_1 S2_1 133.3(9) . . ?
C14_1 C13_1 C12_1 111.8(3) . . ?
C13_1 C14_1 C15_1 114.2(3) . . ?
C14_1 C15_1 C14B_1 35.1(8) . . ?
C14_1 C15_1 S1_1 117.58(19) . . ?
C14B_1 C15_1 S1_1 107.5(9) . . ?
C14B_1 C13B_1 C12_1 107.0(13) . . ?
C13B_1 C14B_1 C15_1 116.2(15) . . ?
C2_2 S1_2 C15_2 103.52(12) . . ?
C10_2 S2_2 C12_2 99.53(11) . . ?
C3_2 C2_2 S1_2 172.7(2) . . ?
C2_2 C3_2 C4_2 177.5(2) . . ?
C3_2 C4_2 C5_2 113.2(2) . . ?
C6_2 C5_2 C4_2 112.29(19) . . ?
C5_2 C6_2 C7_2 113.3(2) . . ?
C6_2 C7_2 C8_2 113.1(2) . . ?
C9_2 C8_2 C7_2 113.6(2) . . ?
C10_2 C9_2 C8_2 178.7(3) . . ?
C9_2 C10_2 S2_2 178.6(2) . . ?
C13_2 C12_2 S2_2 113.98(16) . . ?
C14_2 C13_2 C12_2 111.1(2) . . ?
C15_2 C14_2 C13_2 116.3(2) . . ?
C14_2 C15_2 S1_2 116.68(17) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.08
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052

#===END

data_hse16_(in_paper_5S25)
_database_code_CSD               207501

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 S2'
_chemical_formula_weight         252.42

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   9.1023(2)
_cell_length_b                   16.8216(3)
_cell_length_c                   9.1905(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1407.21(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8868
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13285
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1669
_reflns_number_gt                1382
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.4068P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1669
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.15791(4) 0.57408(2) 0.10741(4) 0.04329(15) Uani 1 1 d . . .
C2 C 0.31124(16) 0.58455(8) 0.00602(15) 0.0364(3) Uani 1 1 d . . .
C3 C 0.41288(17) 0.59091(8) -0.07483(15) 0.0402(3) Uani 1 1 d . A .
C4 C 0.53478(19) 0.60084(10) -0.17777(18) 0.0503(4) Uani 1 1 d . . .
H4A H 0.5387 0.5539 -0.2426 0.060 Uiso 0.764(6) 1 calc PR A 1
H4B H 0.6282 0.6029 -0.1227 0.060 Uiso 0.764(6) 1 calc PR A 1
H4C H 0.5039 0.5800 -0.2738 0.060 Uiso 0.236(6) 1 calc PR A 2
H4D H 0.6188 0.5683 -0.1441 0.060 Uiso 0.236(6) 1 calc PR A 2
C5 C 0.5220(3) 0.67461(13) -0.2695(3) 0.0464(7) Uani 0.764(6) 1 d P . 1
H5A H 0.4270 0.6740 -0.3218 0.056 Uiso 0.764(6) 1 calc PR A 1
H5B H 0.6016 0.6751 -0.3428 0.056 Uiso 0.764(6) 1 calc PR A 1
C6 C 0.5319(3) 0.7500 -0.1764(3) 0.0417(8) Uani 0.764(6) 2 d SP . 1
H6A H 0.4510 0.7500 -0.1043 0.050 Uiso 0.764(6) 2 calc SPR A 1
H6B H 0.6260 0.7500 -0.1224 0.050 Uiso 0.764(6) 2 calc SPR A 1
C7 C 0.21378(19) 0.7500 0.27543(19) 0.0314(4) Uani 1 2 d S . .
H7A H 0.1267 0.7500 0.3399 0.038 Uiso 1 2 calc SR . .
H7B H 0.1789 0.7500 0.1734 0.038 Uiso 1 2 calc SR . .
C8 C 0.30455(14) 0.67565(8) 0.30334(14) 0.0356(3) Uani 1 1 d . . .
H8A H 0.3882 0.6755 0.2346 0.043 Uiso 1 1 calc R . .
H8B H 0.3457 0.6791 0.4028 0.043 Uiso 1 1 calc R . .
C9 C 0.22437(16) 0.59715(8) 0.28919(15) 0.0406(3) Uani 1 1 d . . .
H9A H 0.1396 0.5975 0.3566 0.049 Uiso 1 1 calc R . .
H9B H 0.2913 0.5541 0.3207 0.049 Uiso 1 1 calc R . .
C5B C 0.5859(10) 0.6854(5) -0.1965(11) 0.058(3) Uani 0.236(6) 1 d P . 2
H5B1 H 0.6694 0.6856 -0.2655 0.069 Uiso 0.236(6) 1 calc PR A 2
H5B2 H 0.6233 0.7046 -0.1017 0.069 Uiso 0.236(6) 1 calc PR A 2
C6B C 0.4596(9) 0.7500 -0.2565(9) 0.034(2) Uani 0.236(6) 2 d SP . 2
H6B1 H 0.4439 0.7500 -0.3630 0.041 Uiso 0.236(6) 2 calc SPR A 2
H6B2 H 0.3658 0.7500 -0.2018 0.041 Uiso 0.236(6) 2 calc SPR A 2

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
S1 0.0347(2) 0.0419(2) 0.0533(3) -0.00609(15) 0.00507(15) -0.00576(14)
C2 0.0396(7) 0.0295(6) 0.0401(7) -0.0020(5) -0.0002(6) 0.0044(5)
C3 0.0449(8) 0.0364(7) 0.0392(7) -0.0021(6) 0.0010(6) 0.0055(6)
C4 0.0522(9) 0.0505(9) 0.0482(8) -0.0037(7) 0.0156(7) 0.0100(7)
C5 0.0568(14) 0.0444(11) 0.0379(12) -0.0044(9) 0.0148(11) 0.0017(10)
C6 0.0493(17) 0.0404(15) 0.0354(16) 0.000 0.0110(14) 0.000
C7 0.0260(8) 0.0344(9) 0.0338(9) 0.000 -0.0007(7) 0.000
C8 0.0309(6) 0.0410(7) 0.0348(6) 0.0023(5) -0.0018(5) 0.0052(5)
C9 0.0440(8) 0.0363(7) 0.0413(8) 0.0091(6) 0.0088(6) 0.0053(6)
C5B 0.048(5) 0.075(5) 0.051(5) -0.017(4) 0.018(4) -0.010(4)
C6B 0.032(4) 0.051(5) 0.020(4) 0.000 0.001(3) 0.000

_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
S1 C2 1.6873(15) . ?
S1 C9 1.8186(15) . ?
C2 C3 1.192(2) . ?
C3 C4 1.468(2) . ?
C4 C5 1.505(3) . ?
C4 C5B 1.506(8) . ?
C5 C6 1.532(3) . ?
C6 C5 1.532(3) 7_575 ?
C7 C8 1.5207(16) . ?
C7 C8 1.5207(16) 7_575 ?
C8 C9 1.514(2) . ?
C5B C6B 1.675(13) . ?
C6B C5B 1.675(13) 7_575 ?

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 S1 C9 102.12(7) . . ?
C3 C2 S1 174.91(14) . . ?
C2 C3 C4 177.83(16) . . ?
C3 C4 C5 113.36(14) . . ?
C3 C4 C5B 114.5(3) . . ?
C5 C4 C5B 35.0(4) . . ?
C4 C5 C6 111.4(2) . . ?
C5 C6 C5 111.7(3) 7_575 . ?
C8 C7 C8 110.66(15) . 7_575 ?
C9 C8 C7 116.16(11) . . ?
C8 C9 S1 115.17(9) . . ?
C4 C5B C6B 116.0(7) . . ?
C5B C6B C5B 80.9(8) 7_575 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051

#===END

data_hse20_(in_paper_7S23)
_database_code_CSD               207502

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 S2'
_chemical_formula_weight         252.42

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.4829(2)
_cell_length_b                   10.9233(2)
_cell_length_c                   9.01740(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.9720(10)
_cell_angle_gamma                90.00
_cell_volume                     1421.19(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8967
_exptl_absorpt_correction_T_max  0.9149
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14396
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3258
_reflns_number_gt                2831
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.3626P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3258
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.318
_refine_ls_shift/su_mean         0.017

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
S1 S 1.01295(2) 0.06083(3) 0.22106(4) 0.04089(12) Uani 1 1 d . . .
S2 S 0.74544(2) 0.42657(3) 0.22037(4) 0.03722(11) Uani 1 1 d . . .
C2 C 0.93918(8) -0.03075(11) 0.30583(14) 0.0332(3) Uani 1 1 d . . .
C3 C 0.88919(8) -0.09625(11) 0.36848(14) 0.0328(3) Uani 1 1 d . . .
C4 C 0.82458(9) -0.17633(11) 0.43908(14) 0.0338(3) Uani 1 1 d . . .
H4A H 0.7891 -0.1269 0.5065 0.041 Uiso 1 1 calc R . .
H4B H 0.8604 -0.2382 0.5002 0.041 Uiso 1 1 calc R . .
C5 C 0.75675(9) -0.24187(11) 0.32618(15) 0.0365(3) Uani 1 1 d . . .
H5A H 0.7922 -0.2969 0.2649 0.044 Uiso 1 1 calc R . .
H5B H 0.7148 -0.2934 0.3808 0.044 Uiso 1 1 calc R . .
C6 C 0.69836(9) -0.15604(12) 0.22313(14) 0.0360(3) Uani 1 1 d . . .
H6A H 0.7404 -0.1039 0.1694 0.043 Uiso 1 1 calc R . .
H6B H 0.6612 -0.2058 0.1481 0.043 Uiso 1 1 calc R . .
C7 C 0.63318(9) -0.07365(12) 0.30139(14) 0.0365(3) Uani 1 1 d . . .
H7A H 0.6702 -0.0221 0.3747 0.044 Uiso 1 1 calc R . .
H7B H 0.5917 -0.1253 0.3567 0.044 Uiso 1 1 calc R . .
C8 C 0.57429(9) 0.00900(13) 0.19522(15) 0.0402(3) Uani 1 1 d . . .
H8A H 0.6158 0.0642 0.1448 0.048 Uiso 1 1 calc R . .
H8B H 0.5408 -0.0425 0.1178 0.048 Uiso 1 1 calc R . .
C9 C 0.50403(9) 0.08632(13) 0.26961(17) 0.0436(3) Uani 1 1 d . . .
H9A H 0.4607 0.0310 0.3161 0.052 Uiso 1 1 calc R . .
H9B H 0.4675 0.1344 0.1921 0.052 Uiso 1 1 calc R . .
C10 C 0.54685(9) 0.17423(12) 0.38839(15) 0.0381(3) Uani 1 1 d . . .
H10A H 0.4967 0.2221 0.4289 0.046 Uiso 1 1 calc R . .
H10B H 0.5781 0.1260 0.4711 0.046 Uiso 1 1 calc R . .
C11 C 0.61398(8) 0.25896(11) 0.33168(14) 0.0322(3) Uani 1 1 d . . .
C12 C 0.66925(8) 0.32570(11) 0.28272(14) 0.0309(3) Uani 1 1 d . . .
C14 C 0.81442(8) 0.32769(11) 0.11104(13) 0.0310(3) Uani 1 1 d . . .
H14A H 0.7725 0.2817 0.0386 0.037 Uiso 1 1 calc R . .
H14B H 0.8552 0.3791 0.0541 0.037 Uiso 1 1 calc R . .
C15 C 0.87374(8) 0.23735(11) 0.20562(12) 0.0291(2) Uani 1 1 d . . .
H15A H 0.9149 0.2828 0.2797 0.035 Uiso 1 1 calc R . .
H15B H 0.8331 0.1839 0.2604 0.035 Uiso 1 1 calc R . .
C16 C 0.93197(8) 0.15895(11) 0.11107(13) 0.0308(3) Uani 1 1 d . . .
H16A H 0.9671 0.2129 0.0480 0.037 Uiso 1 1 calc R . .
H16B H 0.8904 0.1073 0.0443 0.037 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
S1 0.02495(17) 0.0423(2) 0.0556(2) 0.01026(15) 0.00436(14) 0.00302(12)
S2 0.03306(18) 0.02300(16) 0.0564(2) 0.00260(13) 0.00850(14) -0.00128(11)
C2 0.0313(6) 0.0304(6) 0.0374(6) 0.0000(5) -0.0003(5) 0.0059(5)
C3 0.0322(6) 0.0303(6) 0.0356(6) 0.0002(5) 0.0000(5) 0.0065(5)
C4 0.0375(6) 0.0317(6) 0.0329(6) 0.0024(5) 0.0075(5) 0.0060(5)
C5 0.0435(7) 0.0277(6) 0.0402(7) -0.0050(5) 0.0140(5) -0.0022(5)
C6 0.0370(7) 0.0414(7) 0.0300(6) -0.0064(5) 0.0055(5) -0.0079(5)
C7 0.0383(7) 0.0395(7) 0.0317(6) 0.0011(5) 0.0029(5) 0.0009(5)
C8 0.0415(7) 0.0395(7) 0.0379(7) 0.0047(6) -0.0070(5) -0.0080(6)
C9 0.0274(6) 0.0421(7) 0.0598(9) 0.0138(6) -0.0044(6) -0.0051(5)
C10 0.0303(6) 0.0384(7) 0.0469(7) 0.0104(6) 0.0110(5) 0.0037(5)
C11 0.0276(6) 0.0311(6) 0.0380(6) 0.0019(5) 0.0033(5) 0.0053(5)
C12 0.0273(6) 0.0289(6) 0.0363(6) 0.0022(5) 0.0012(5) 0.0036(5)
C14 0.0308(6) 0.0311(6) 0.0313(6) 0.0052(5) 0.0036(5) -0.0012(5)
C15 0.0321(6) 0.0309(6) 0.0243(5) 0.0024(4) 0.0028(4) 0.0009(5)
C16 0.0301(6) 0.0340(6) 0.0285(6) 0.0024(5) 0.0041(4) -0.0005(5)

_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
S1 C2 1.6934(13) . ?
S1 C16 1.8183(12) . ?
S2 C12 1.6898(12) . ?
S2 C14 1.8187(12) . ?
C2 C3 1.1942(18) . ?
C3 C4 1.4661(17) . ?
C4 C5 1.5299(18) . ?
C5 C6 1.5236(19) . ?
C6 C7 1.5213(18) . ?
C7 C8 1.5223(18) . ?
C8 C9 1.522(2) . ?
C9 C10 1.529(2) . ?
C10 C11 1.4661(17) . ?
C11 C12 1.1951(17) . ?
C14 C15 1.5206(15) . ?
C15 C16 1.5153(16) . ?

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 S1 C16 101.07(6) . . ?
C12 S2 C14 101.44(6) . . ?
C3 C2 S1 178.14(11) . . ?
C2 C3 C4 177.24(13) . . ?
C3 C4 C5 112.80(10) . . ?
C6 C5 C4 114.10(10) . . ?
C7 C6 C5 114.52(10) . . ?
C6 C7 C8 113.30(11) . . ?
C9 C8 C7 114.29(11) . . ?
C8 C9 C10 114.27(11) . . ?
C11 C10 C9 113.14(11) . . ?
C12 C11 C10 178.24(14) . . ?
C11 C12 S2 176.61(12) . . ?
C15 C14 S2 113.05(8) . . ?
C16 C15 C14 111.48(9) . . ?
C15 C16 S1 112.98(8) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.053

#===END

data_hse18_(in_paper_7S25)
_database_code_CSD               207503

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 S2'
_chemical_formula_weight         280.47

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc

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

_cell_length_a                   4.5938(2)
_cell_length_b                   17.1826(9)
_cell_length_c                   9.9664(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1660(10)
_cell_angle_gamma                90.00
_cell_volume                     785.48(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          3.00
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4454
_exptl_absorpt_correction_T_max  0.9810
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7873
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.19
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3532
_reflns_number_gt                3127
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.0621P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_number_reflns         3532
_refine_ls_number_parameters     164
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
S1 S 0.06178(12) -0.01093(3) 0.14999(6) 0.03851(16) Uani 1 1 d . . .
S2 S 0.13644(10) 0.35316(3) 0.67039(5) 0.03606(15) Uani 1 1 d . . .
C2 C -0.0867(4) 0.05236(12) 0.03651(19) 0.0295(4) Uani 1 1 d . . .
C3 C -0.2034(5) 0.09556(11) -0.0439(2) 0.0296(4) Uani 1 1 d . . .
C4 C -0.3544(5) 0.15019(12) -0.13948(19) 0.0293(4) Uani 1 1 d . . .
H4A H -0.4886 0.1208 -0.2019 0.035 Uiso 1 1 calc R . .
H4B H -0.2091 0.1768 -0.1932 0.035 Uiso 1 1 calc R . .
C5 C -0.5303(5) 0.21202(12) -0.0625(2) 0.0306(4) Uani 1 1 d . . .
H5A H -0.6537 0.2421 -0.1286 0.037 Uiso 1 1 calc R . .
H5B H -0.6618 0.1846 -0.0028 0.037 Uiso 1 1 calc R . .
C6 C -0.3431(5) 0.26834(12) 0.0212(2) 0.0306(4) Uani 1 1 d . . .
H6A H -0.2133 0.2963 -0.0385 0.037 Uiso 1 1 calc R . .
H6B H -0.2184 0.2384 0.0868 0.037 Uiso 1 1 calc R . .
C7 C -0.5173(5) 0.32776(11) 0.0968(2) 0.0280(4) Uani 1 1 d . . .
H7A H -0.6342 0.3597 0.0310 0.034 Uiso 1 1 calc R . .
H7B H -0.6544 0.2999 0.1531 0.034 Uiso 1 1 calc R . .
C8 C -0.3277(5) 0.38118(11) 0.1857(2) 0.0283(4) Uani 1 1 d . . .
H8A H -0.1874 0.4080 0.1297 0.034 Uiso 1 1 calc R . .
H8B H -0.2143 0.3493 0.2528 0.034 Uiso 1 1 calc R . .
C9 C -0.5003(5) 0.44196(12) 0.2591(2) 0.0325(5) Uani 1 1 d . . .
H9A H -0.6490 0.4152 0.3105 0.039 Uiso 1 1 calc R . .
H9B H -0.6040 0.4758 0.1918 0.039 Uiso 1 1 calc R . .
C10 C -0.3092(5) 0.49380(12) 0.3572(2) 0.0333(5) Uani 1 1 d . . .
H10A H -0.1628 0.5218 0.3061 0.040 Uiso 1 1 calc R . .
H10B H -0.4342 0.5330 0.3985 0.040 Uiso 1 1 calc R . .
C11 C -0.1575(5) 0.44661(12) 0.4646(2) 0.0300(4) Uani 1 1 d . . .
C12 C -0.0331(5) 0.40748(11) 0.5489(2) 0.0286(4) Uani 1 1 d . . .
C14 C 0.3354(5) 0.28518(11) 0.5694(2) 0.0293(4) Uani 1 1 d . . .
H14A H 0.4535 0.3151 0.5072 0.035 Uiso 1 1 calc R . .
H14B H 0.4713 0.2548 0.6295 0.035 Uiso 1 1 calc R . .
C15 C 0.1408(4) 0.22945(12) 0.4885(2) 0.0279(4) Uani 1 1 d . . .
H15A H 0.0127 0.2595 0.4243 0.033 Uiso 1 1 calc R . .
H15B H 0.0148 0.2014 0.5499 0.033 Uiso 1 1 calc R . .
C16 C 0.3135(4) 0.17025(11) 0.4109(2) 0.0277(4) Uani 1 1 d . . .
H16A H 0.4477 0.1982 0.3532 0.033 Uiso 1 1 calc R . .
H16B H 0.4330 0.1381 0.4753 0.033 Uiso 1 1 calc R . .
C17 C 0.1166(4) 0.11732(12) 0.3236(2) 0.0266(4) Uani 1 1 d . . .
H17A H -0.0292 0.0929 0.3798 0.032 Uiso 1 1 calc R . .
H17B H 0.0104 0.1489 0.2537 0.032 Uiso 1 1 calc R . .
C18 C 0.2870(5) 0.05417(12) 0.2565(2) 0.0309(5) Uani 1 1 d . . .
H18A H 0.3933 0.0230 0.3269 0.037 Uiso 1 1 calc R . .
H18B H 0.4337 0.0790 0.2012 0.037 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
S1 0.0565(4) 0.0247(2) 0.0335(3) -0.0027(2) -0.0048(2) 0.0076(2)
S2 0.0501(3) 0.0291(3) 0.0285(3) -0.0040(2) -0.0020(2) 0.0056(2)
C2 0.0376(12) 0.0248(10) 0.0264(10) -0.0060(8) 0.0039(9) 0.0014(8)
C3 0.0356(11) 0.0261(10) 0.0268(10) -0.0056(8) -0.0003(8) -0.0019(8)
C4 0.0374(11) 0.0223(10) 0.0272(10) 0.0027(8) -0.0066(9) 0.0027(9)
C5 0.0311(11) 0.0274(10) 0.0327(10) 0.0016(8) -0.0053(9) 0.0008(9)
C6 0.0299(11) 0.0261(10) 0.0357(11) -0.0021(8) 0.0015(9) 0.0006(8)
C7 0.0261(10) 0.0267(9) 0.0313(10) 0.0041(8) 0.0031(8) 0.0006(8)
C8 0.0295(11) 0.0255(9) 0.0299(10) -0.0005(8) 0.0029(8) 0.0046(8)
C9 0.0362(11) 0.0283(11) 0.0328(11) 0.0014(8) 0.0014(9) 0.0096(9)
C10 0.0439(13) 0.0275(10) 0.0283(10) 0.0000(8) 0.0010(9) 0.0115(9)
C11 0.0345(11) 0.0251(10) 0.0310(10) -0.0048(8) 0.0080(9) 0.0019(8)
C12 0.0335(11) 0.0225(9) 0.0301(10) -0.0063(8) 0.0040(9) 0.0006(8)
C14 0.0314(11) 0.0251(9) 0.0311(10) -0.0022(8) 0.0003(8) 0.0039(8)
C15 0.0272(11) 0.0246(9) 0.0320(10) -0.0037(8) 0.0025(8) 0.0005(8)
C16 0.0286(11) 0.0249(10) 0.0299(10) -0.0015(8) 0.0036(9) 0.0014(8)
C17 0.0299(11) 0.0225(9) 0.0274(9) -0.0020(7) 0.0010(8) 0.0041(8)
C18 0.0330(12) 0.0303(11) 0.0292(10) -0.0057(8) -0.0007(9) 0.0089(9)

_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
S1 C2 1.686(2) . ?
S1 C18 1.824(2) . ?
S2 C12 1.685(2) . ?
S2 C14 1.821(2) . ?
C2 C3 1.197(3) . ?
C3 C4 1.482(3) . ?
C4 C5 1.562(3) . ?
C5 C6 1.514(3) . ?
C6 C7 1.522(3) . ?
C7 C8 1.517(3) . ?
C8 C9 1.522(3) . ?
C9 C10 1.557(3) . ?
C10 C11 1.486(3) . ?
C11 C12 1.196(3) . ?
C14 C15 1.512(3) . ?
C15 C16 1.527(3) . ?
C16 C17 1.522(3) . ?
C17 C18 1.515(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
C2 S1 C18 100.97(9) . . ?
C12 S2 C14 100.62(10) . . ?
C3 C2 S1 177.2(2) . . ?
C2 C3 C4 177.9(2) . . ?
C3 C4 C5 110.58(16) . . ?
C6 C5 C4 114.31(17) . . ?
C5 C6 C7 113.78(17) . . ?
C8 C7 C6 113.23(17) . . ?
C7 C8 C9 113.46(17) . . ?
C8 C9 C10 113.80(17) . . ?
C11 C10 C9 111.47(17) . . ?
C12 C11 C10 178.5(2) . . ?
C11 C12 S2 178.57(19) . . ?
C15 C14 S2 113.63(14) . . ?
C14 C15 C16 112.55(15) . . ?
C17 C16 C15 112.27(16) . . ?
C18 C17 C16 112.04(16) . . ?
C17 C18 S1 113.94(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.044

#===END

data_hse23_(in_paper_5Se22)
_database_code_CSD               207504

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 Se2'
_chemical_formula_weight         304.14

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P-4

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'

_cell_length_a                   15.4224(13)
_cell_length_b                   15.4224(13)
_cell_length_c                   4.8824(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1161.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    6.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0956
_exptl_absorpt_correction_T_max  0.5175
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2215
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.39
_reflns_number_total             1965
_reflns_number_gt                1666
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.1845P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_number_reflns         1965
_refine_ls_number_parameters     137
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.079
_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
Se1 Se 0.38432(4) 0.42737(4) 0.78566(17) 0.0401(2) Uani 1 1 d DU . .
Se2 Se 0.34463(6) 0.14612(5) 1.1241(2) 0.0565(3) Uani 1 1 d DU . .
C12 C 0.3833(6) 0.2452(5) 0.899(2) 0.034(2) Uani 0.743(14) 1 d PDU A 1
H12A H 0.4473 0.2459 0.8881 0.041 Uiso 0.743(14) 1 calc PR A 1
H12B H 0.3598 0.2399 0.7115 0.041 Uiso 0.743(14) 1 calc PR A 1
C13 C 0.3518(6) 0.3265(5) 1.0277(19) 0.030(2) Uani 0.743(14) 1 d PDU A 1
H13A H 0.3783 0.3337 1.2110 0.036 Uiso 0.743(14) 1 calc PR A 1
H13B H 0.2880 0.3242 1.0502 0.036 Uiso 0.743(14) 1 calc PR A 1
C2 C 0.2747(5) 0.4401(4) 0.6456(18) 0.0395(18) Uani 1 1 d . A .
C3 C 0.2032(5) 0.4447(5) 0.558(2) 0.053(2) Uani 1 1 d . . .
C4 C 0.1144(6) 0.4427(6) 0.450(3) 0.089(4) Uani 1 1 d . A .
H4A H 0.0767 0.4769 0.5735 0.107 Uiso 1 1 calc R . .
H4B H 0.1141 0.4716 0.2690 0.107 Uiso 1 1 calc R . .
C5 C 0.0780(7) 0.3592(8) 0.420(3) 0.112(5) Uani 1 1 d . . .
H5A H 0.0145 0.3676 0.4326 0.134 Uiso 1 1 calc R A .
H5B H 0.0899 0.3421 0.2280 0.134 Uiso 1 1 calc R . .
C6 C 0.0958(7) 0.2854(6) 0.577(4) 0.124(8) Uani 1 1 d . A .
H6A H 0.1581 0.2746 0.5415 0.149 Uiso 1 1 calc R . .
H6B H 0.0931 0.3071 0.7675 0.149 Uiso 1 1 calc R . .
C7 C 0.0621(7) 0.2055(10) 0.595(4) 0.128(6) Uani 1 1 d . . .
H7A H 0.0003 0.2161 0.6381 0.153 Uiso 1 1 calc R A .
H7B H 0.0627 0.1845 0.4034 0.153 Uiso 1 1 calc R . .
C8 C 0.0815(5) 0.1348(5) 0.741(3) 0.081(4) Uani 1 1 d . A .
H8A H 0.0765 0.0835 0.6206 0.097 Uiso 1 1 calc R . .
H8B H 0.0377 0.1284 0.8884 0.097 Uiso 1 1 calc R . .
C9 C 0.1671(5) 0.1340(5) 0.866(2) 0.054(3) Uani 1 1 d . . .
C10 C 0.2359(5) 0.1372(5) 0.9734(19) 0.0433(19) Uani 1 1 d . A .
C12B C 0.3446(14) 0.2776(9) 1.097(5) 0.027(6) Uani 0.257(14) 1 d PDU A 2
H12C H 0.2844 0.2998 1.1030 0.033 Uiso 0.257(14) 1 calc PR A 2
H12D H 0.3773 0.3030 1.2516 0.033 Uiso 0.257(14) 1 calc PR A 2
C13B C 0.3857(14) 0.3013(9) 0.835(4) 0.021(6) Uani 0.257(14) 1 d PDU A 2
H13C H 0.3542 0.2733 0.6822 0.025 Uiso 0.257(14) 1 calc PR A 2
H13D H 0.4463 0.2802 0.8329 0.025 Uiso 0.257(14) 1 calc PR A 2

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 0.0361(4) 0.0278(3) 0.0562(5) -0.0010(4) -0.0084(4) -0.0029(3)
Se2 0.0620(6) 0.0473(5) 0.0602(6) 0.0198(4) -0.0184(5) -0.0168(4)
C12 0.034(5) 0.032(5) 0.036(6) -0.005(4) 0.002(5) -0.001(4)
C13 0.039(5) 0.034(4) 0.018(5) -0.003(4) -0.003(4) 0.003(5)
C2 0.046(4) 0.027(3) 0.046(5) 0.002(3) 0.004(4) -0.003(3)
C3 0.048(5) 0.034(4) 0.078(7) 0.003(4) -0.019(5) 0.001(4)
C4 0.061(6) 0.061(6) 0.146(13) 0.009(7) -0.058(7) -0.004(5)
C5 0.061(6) 0.153(11) 0.123(12) 0.065(10) -0.062(8) -0.028(7)
C6 0.083(7) 0.047(5) 0.24(2) -0.015(9) -0.097(11) 0.009(5)
C7 0.074(7) 0.195(15) 0.114(12) 0.065(12) -0.053(9) -0.081(9)
C8 0.037(4) 0.052(5) 0.152(12) -0.014(7) -0.013(7) -0.014(4)
C9 0.043(4) 0.038(4) 0.083(8) -0.015(5) 0.012(5) -0.007(3)
C10 0.045(4) 0.042(4) 0.043(5) -0.003(4) 0.009(4) -0.006(3)
C12B 0.007(10) 0.041(9) 0.034(15) -0.003(11) 0.006(10) 0.004(11)
C13B 0.034(13) 0.016(7) 0.014(12) -0.006(8) 0.000(10) 0.017(9)

_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 C2 1.835(7) . ?
Se1 C13B 1.959(13) . ?
Se1 C13 2.017(8) . ?
Se2 C10 1.836(9) . ?
Se2 C12 1.973(8) . ?
Se2 C12B 2.032(14) . ?
C12 C13 1.484(11) . ?
C2 C3 1.183(10) . ?
C3 C4 1.469(11) . ?
C4 C5 1.413(14) . ?
C5 C6 1.399(17) . ?
C6 C7 1.340(15) . ?
C7 C8 1.338(16) . ?
C8 C9 1.453(13) . ?
C9 C10 1.184(11) . ?
C12B C13B 1.472(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
C2 Se1 C13B 99.3(7) . . ?
C2 Se1 C13 94.1(4) . . ?
C13B Se1 C13 33.4(6) . . ?
C10 Se2 C12 96.4(4) . . ?
C10 Se2 C12B 92.7(7) . . ?
C12 Se2 C12B 36.0(7) . . ?
C13 C12 Se2 108.7(6) . . ?
C12 C13 Se1 108.9(6) . . ?
C3 C2 Se1 177.2(7) . . ?
C2 C3 C4 175.4(8) . . ?
C5 C4 C3 115.3(8) . . ?
C6 C5 C4 127.3(11) . . ?
C7 C6 C5 135.0(12) . . ?
C8 C7 C6 134.3(12) . . ?
C7 C8 C9 115.7(8) . . ?
C10 C9 C8 176.8(9) . . ?
C9 C10 Se2 176.8(8) . . ?
C13B C12B Se2 107.8(12) . . ?
C12B C13B Se1 110.4(12) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.106

#===END

data_dwe91_(in_paper_5te23)
_database_code_CSD               207505

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Te2'
_chemical_formula_weight         415.45

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'
Te Te -0.5308 1.6751 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.8259(3)
_cell_length_b                   4.73160(10)
_cell_length_c                   14.5466(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7260(10)
_cell_angle_gamma                90.00
_cell_volume                     656.99(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    4.404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1775
_exptl_absorpt_correction_T_max  0.9171
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-38.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6353
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2966
_reflns_number_gt                2464
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_number_reflns         2966
_refine_ls_number_parameters     127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Te1 Te -0.16436(3) 0.30415(18) 0.69426(2) 0.02914(12) Uani 1 1 d . . .
Te2 Te 0.35922(3) 0.30281(15) 0.52256(2) 0.02284(11) Uani 1 1 d . . .
C2 C -0.0306(7) 0.4959(15) 0.8087(5) 0.0311(15) Uani 1 1 d . . .
C3 C 0.0447(7) 0.6012(17) 0.8731(5) 0.0371(16) Uani 1 1 d . . .
C4 C 0.1441(7) 0.747(3) 0.9532(5) 0.055(4) Uani 1 1 d . . .
H4A H 0.1897 0.6032 0.9998 0.066 Uiso 1 1 calc R . .
H4B H 0.0899 0.8744 0.9851 0.066 Uiso 1 1 calc R . .
C5 C 0.2562(7) 0.9170(18) 0.9235(5) 0.0398(18) Uani 1 1 d . . .
H5A H 0.3139 1.0117 0.9802 0.048 Uiso 1 1 calc R . .
H5B H 0.2103 1.0664 0.8792 0.048 Uiso 1 1 calc R . .
C6 C 0.3533(7) 0.7487(16) 0.8762(4) 0.030(2) Uani 1 1 d . . .
H6A H 0.3969 0.5944 0.9191 0.036 Uiso 1 1 calc R . .
H6B H 0.2968 0.6610 0.8177 0.036 Uiso 1 1 calc R . .
C7 C 0.4688(7) 0.9270(15) 0.8511(5) 0.0372(17) Uani 1 1 d . . .
H7A H 0.5222 1.0232 0.9089 0.045 Uiso 1 1 calc R . .
H7B H 0.4255 1.0745 0.8051 0.045 Uiso 1 1 calc R . .
C8 C 0.5702(6) 0.7512(19) 0.8086(4) 0.034(2) Uani 1 1 d . . .
H8A H 0.6463 0.8761 0.7988 0.041 Uiso 1 1 calc R . .
H8B H 0.6132 0.6044 0.8550 0.041 Uiso 1 1 calc R . .
C9 C 0.5058(6) 0.6134(15) 0.7189(4) 0.0274(14) Uani 1 1 d . . .
C10 C 0.4500(6) 0.5005(14) 0.6484(4) 0.0251(14) Uani 1 1 d . . .
C12 C 0.2114(6) 0.0753(15) 0.5851(4) 0.0271(14) Uani 1 1 d . . .
H12A H 0.1587 -0.0594 0.5377 0.033 Uiso 1 1 calc R . .
H12B H 0.2647 -0.0365 0.6393 0.033 Uiso 1 1 calc R . .
C13 C 0.1072(5) 0.260(2) 0.6193(4) 0.026(2) Uani 1 1 d . . .
H13A H 0.0555 0.3797 0.5667 0.031 Uiso 1 1 calc R . .
H13B H 0.1575 0.3855 0.6707 0.031 Uiso 1 1 calc R . .
C14 C 0.0042(6) 0.0740(15) 0.6557(4) 0.0255(13) Uani 1 1 d . . .
H14A H 0.0564 -0.0321 0.7117 0.031 Uiso 1 1 calc R . .
H14B H -0.0368 -0.0657 0.6062 0.031 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
Te1 0.01885(17) 0.0332(2) 0.0400(2) 0.0074(5) 0.01616(14) 0.0003(5)
Te2 0.01670(16) 0.02809(19) 0.02625(18) -0.0007(4) 0.01009(12) 0.0032(4)
C2 0.032(4) 0.034(4) 0.032(4) 0.006(3) 0.018(3) 0.008(3)
C3 0.033(4) 0.047(4) 0.036(4) 0.003(3) 0.017(3) 0.007(3)
C4 0.036(3) 0.100(13) 0.033(3) -0.018(5) 0.018(3) 0.016(5)
C5 0.046(4) 0.045(4) 0.028(4) -0.012(3) 0.008(3) -0.001(3)
C6 0.033(3) 0.031(7) 0.027(3) -0.003(3) 0.008(2) 0.001(3)
C7 0.048(4) 0.037(4) 0.026(3) -0.010(3) 0.008(3) -0.007(3)
C8 0.029(3) 0.035(8) 0.041(3) -0.002(3) 0.014(3) -0.010(3)
C9 0.017(3) 0.043(4) 0.027(3) 0.010(3) 0.014(2) -0.003(3)
C10 0.014(3) 0.038(4) 0.026(3) 0.007(3) 0.009(2) 0.005(3)
C12 0.016(3) 0.026(3) 0.041(4) 0.002(3) 0.010(3) 0.002(3)
C13 0.018(2) 0.029(7) 0.034(3) 0.000(3) 0.013(2) 0.003(3)
C14 0.022(3) 0.024(3) 0.033(3) 0.000(3) 0.011(3) -0.002(3)

_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
Te1 C2 2.070(7) . ?
Te1 C14 2.164(6) . ?
Te2 C10 2.061(6) . ?
Te2 C12 2.174(6) . ?
C2 C3 1.160(9) . ?
C3 C4 1.499(11) . ?
C4 C5 1.507(11) . ?
C5 C6 1.526(9) . ?
C6 C7 1.526(9) . ?
C7 C8 1.536(9) . ?
C8 C9 1.462(9) . ?
C9 C10 1.171(8) . ?
C12 C13 1.517(9) . ?
C13 C14 1.527(9) . ?

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 Te1 C14 92.9(2) . . ?
C10 Te2 C12 92.5(2) . . ?
C3 C2 Te1 179.4(7) . . ?
C2 C3 C4 177.2(9) . . ?
C3 C4 C5 114.2(6) . . ?
C4 C5 C6 115.4(7) . . ?
C7 C6 C5 113.5(6) . . ?
C6 C7 C8 112.8(6) . . ?
C9 C8 C7 114.6(5) . . ?
C10 C9 C8 177.5(6) . . ?
C9 C10 Te2 177.7(5) . . ?
C13 C12 Te2 115.0(5) . . ?
C12 C13 C14 109.6(8) . . ?
C13 C14 Te1 114.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.935
_refine_diff_density_min         -1.128
_refine_diff_density_rms         0.153

#===END

#_eof  End of Crystallographic Information File