Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm
_journal_coden_Cambridge         1350
_publ_contact_author_name        'Simon E. Lawrence'
_publ_contact_author_address     
;Department of Chemistry
University College Cork
Cork
Ireland
;
_publ_contact_author_email       s.lawrence@ucc.ie
_publ_contact_author_phone       +353(21)4903143
_publ_contact_author_fax         +353(21)4274097
loop_
_publ_author_name
_publ_author_address
K.N.Lehane
;Department of Chemistry
Analytical and Biological Chemistry Research Facility
University College Cork
Cork
Ireland
;
E.J.A.Moynihan
;Department of Chemistry
Analytical and Biological Chemistry Research Facility
University College Cork
Cork
Ireland
;
N.Brondel
;Department of Chemistry
Analytical and Biological Chemistry Research Facility
University College Cork
Cork
Ireland
;
S.E.Lawrence
;Department of Chemistry
Analytical and Biological Chemistry Research Facility
University College Cork
Cork
Ireland
;
A.R.Maguire
;Department of Chemistry
Analytical and Biological Chemistry Research Facility
University College Cork
Cork
Ireland
;
_publ_section_title              
;
Impact of sulfur substituents on the C-H...O
interaction of terminal alkynes in crystal engineering
;
#=====================================================================
data_Compound+/-1
_database_code_depnum_ccdc_archive 'CCDC 253938'
#=====================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 O S'
_chemical_formula_sum            'C9 H8 O S'
_chemical_formula_weight         164.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   14.745(2)
_cell_length_b                   5.7176(5)
_cell_length_c                   20.659(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1741.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      8.49
_cell_measurement_theta_max      15.51

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Nonius MACH3'
_diffrn_measurement_method       '\w-2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1912
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.1096
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.45
_reflns_number_total             1615
_reflns_number_gt                741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'PLATON (Spek, 1999)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL--97; PLATON'

_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^)+(0.0471P)^2^+0.5339P] 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         1615
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1854
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
S9 S 0.42495(8) 0.7448(2) 0.44491(5) 0.0593(4) Uani 1 1 d . . .
O10 O 0.3883(2) 0.5034(5) 0.45396(13) 0.0717(10) Uani 1 1 d . . .
C2 C 0.3650(3) 0.9919(9) 0.1659(2) 0.0579(13) Uani 1 1 d . . .
C6 C 0.4005(3) 0.8279(7) 0.36280(19) 0.0449(11) Uani 1 1 d . . .
C7 C 0.4342(3) 1.0366(8) 0.3385(2) 0.0539(12) Uani 1 1 d . . .
H7 H 0.4654 1.1393 0.3654 0.065 Uiso 1 1 calc R . .
C4 C 0.3412(3) 0.7303(9) 0.2588(2) 0.0527(11) Uani 1 1 d . . .
H4 H 0.3094 0.6282 0.2321 0.063 Uiso 1 1 calc R . .
C3 C 0.3754(3) 0.9391(8) 0.2339(2) 0.0489(11) Uani 1 1 d . . .
C8 C 0.4209(3) 1.0903(8) 0.2744(2) 0.0559(12) Uani 1 1 d . . .
H8 H 0.4430 1.2308 0.2581 0.067 Uiso 1 1 calc R . .
C5 C 0.3544(3) 0.6755(7) 0.3229(2) 0.0520(12) Uani 1 1 d . . .
H5 H 0.3323 0.5353 0.3393 0.062 Uiso 1 1 calc R . .
C11 C 0.3472(3) 0.9398(7) 0.4834(2) 0.0718(15) Uani 1 1 d . . .
H11A H 0.2879 0.9192 0.4652 0.108 Uiso 1 1 calc R . .
H11B H 0.3667 1.0982 0.4768 0.108 Uiso 1 1 calc R . .
H11C H 0.3453 0.9069 0.5289 0.108 Uiso 1 1 calc R . .
C1 C 0.3601(4) 1.0361(9) 0.1111(2) 0.0810(17) Uani 1 1 d . . .
H1 H 0.3562 1.0715 0.0673 0.097 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
S9 0.0757(8) 0.0510(7) 0.0512(6) 0.0033(7) -0.0034(7) 0.0027(8)
O10 0.119(3) 0.0379(17) 0.0587(19) 0.0096(17) 0.0037(19) 0.0000(18)
C2 0.053(3) 0.062(3) 0.058(3) 0.008(3) 0.002(3) 0.001(3)
C6 0.049(3) 0.038(2) 0.047(2) 0.000(2) -0.001(2) 0.004(2)
C7 0.068(3) 0.040(3) 0.053(3) -0.006(2) 0.000(3) -0.014(3)
C4 0.052(3) 0.054(3) 0.052(3) -0.001(3) -0.003(2) -0.006(3)
C3 0.046(3) 0.050(3) 0.051(3) 0.009(2) 0.004(2) 0.007(3)
C8 0.060(3) 0.046(3) 0.061(3) 0.003(2) 0.010(3) -0.008(3)
C5 0.060(3) 0.038(3) 0.059(3) 0.004(2) 0.003(2) -0.009(2)
C11 0.106(4) 0.052(3) 0.058(3) -0.003(3) 0.018(3) 0.003(3)
C1 0.102(4) 0.079(4) 0.061(3) 0.011(3) -0.002(3) -0.004(4)

_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
S9 O10 1.494(3) . ?
S9 C11 1.786(4) . ?
S9 C6 1.798(4) . ?
C2 C1 1.161(6) . ?
C2 C3 1.444(6) . ?
C6 C5 1.379(5) . ?
C6 C7 1.386(5) . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C4 C5 1.374(6) . ?
C4 C3 1.395(5) . ?
C4 H4 0.9300 . ?
C3 C8 1.378(5) . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C1 H1 0.9300 . ?

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
O10 S9 C11 106.8(2) . . ?
O10 S9 C6 106.84(19) . . ?
C11 S9 C6 97.3(2) . . ?
C1 C2 C3 177.4(6) . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 S9 119.7(3) . . ?
C7 C6 S9 119.8(3) . . ?
C8 C7 C6 119.3(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C8 C3 C4 119.2(4) . . ?
C8 C3 C2 120.8(4) . . ?
C4 C3 C2 120.0(4) . . ?
C7 C8 C3 121.1(4) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
S9 C11 H11A 109.5 . . ?
S9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C1 H1 180.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 S9 C6 C5 1.0(4) . . . . ?
C11 S9 C6 C5 -109.1(4) . . . . ?
O10 S9 C6 C7 -174.0(3) . . . . ?
C11 S9 C6 C7 75.9(4) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
S9 C6 C7 C8 175.1(3) . . . . ?
C5 C4 C3 C8 -1.2(6) . . . . ?
C5 C4 C3 C2 177.2(4) . . . . ?
C6 C7 C8 C3 -0.5(7) . . . . ?
C4 C3 C8 C7 1.0(6) . . . . ?
C2 C3 C8 C7 -177.4(4) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C7 C6 C5 C4 -0.3(6) . . . . ?
S9 C6 C5 C4 -175.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.45
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.057

#=====================================================================
# END of data_Compound+/-1 CIF
#=====================================================================

#=====================================================================
data_Compound(S)1
_database_code_depnum_ccdc_archive 'CCDC 253939'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 O S'
_chemical_formula_sum            'C9 H8 O S'
_chemical_formula_weight         164.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.9369(6)
_cell_length_b                   10.9023(10)
_cell_length_c                   13.2907(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     860.25(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      15.64
_cell_measurement_theta_max      17.79

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Nonius MACH3'
_diffrn_measurement_method       '\w-2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1896
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.46
_reflns_number_total             1584
_reflns_number_gt                1467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'maXus (Gilmore et al, 1998)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL--97; PLATON'

_refine_special_details          
;
The absolute configuration was checked by refinement in SHELXL-97 using
TWIN and BASF to give 0.00001 for the correct enantiomer, with
R1=0.029 and wR2=0.084. The incorrect enantiomer refined to R1=0.030
and wR2 0.087.

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^)+(0.0474P)^2^+0.1106P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_chemical_absolute_configuration ad
_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   -0.04(11)
_refine_ls_number_reflns         1584
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1910(4) 0.53060(19) 0.32289(17) 0.0592(6) Uani 1 1 d . . .
H1 H 0.2006 0.6151 0.3141 0.071 Uiso 1 1 calc R . .
C2 C 0.1787(4) 0.42353(19) 0.33396(15) 0.0517(5) Uani 1 1 d . . .
C3 C 0.1613(3) 0.29321(17) 0.35051(14) 0.0454(4) Uani 1 1 d . . .
C4 C -0.0225(4) 0.24641(18) 0.40285(15) 0.0514(5) Uani 1 1 d . . .
H4 H -0.1344 0.2992 0.4259 0.062 Uiso 1 1 calc R . .
C5 C -0.0398(3) 0.12155(18) 0.42085(15) 0.0514(5) Uani 1 1 d . . .
H5 H -0.1636 0.0901 0.4551 0.062 Uiso 1 1 calc R . .
C6 C 0.1293(3) 0.04408(16) 0.38739(13) 0.0443(4) Uani 1 1 d . . .
C7 C 0.3113(4) 0.08866(18) 0.33459(16) 0.0504(5) Uani 1 1 d . . .
H7 H 0.4221 0.0354 0.3113 0.060 Uiso 1 1 calc R . .
C8 C 0.3282(4) 0.21355(19) 0.31637(15) 0.0515(5) Uani 1 1 d . . .
H8 H 0.4513 0.2443 0.2812 0.062 Uiso 1 1 calc R . .
C11 C 0.1885(5) -0.1197(2) 0.53553(18) 0.0732(7) Uani 1 1 d . . .
H11A H 0.1744 -0.2013 0.5619 0.110 Uiso 1 1 calc R . .
H11B H 0.0965 -0.0647 0.5743 0.110 Uiso 1 1 calc R . .
H11C H 0.3429 -0.0941 0.5394 0.110 Uiso 1 1 calc R . .
O10 O 0.2752(4) -0.18106(13) 0.34909(15) 0.0851(6) Uani 1 1 d . . .
S9 S 0.09836(10) -0.11764(4) 0.40750(4) 0.05619(18) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0746(15) 0.0376(11) 0.0655(13) 0.0035(10) 0.0028(11) 0.0001(10)
C2 0.0631(13) 0.0439(11) 0.0482(10) 0.0012(8) -0.0018(10) 0.0008(9)
C3 0.0584(12) 0.0354(9) 0.0425(9) -0.0001(7) -0.0033(9) -0.0009(8)
C4 0.0538(11) 0.0408(10) 0.0596(11) -0.0040(10) 0.0079(10) 0.0052(8)
C5 0.0531(11) 0.0416(10) 0.0594(11) 0.0012(10) 0.0117(9) -0.0032(9)
C6 0.0547(11) 0.0314(8) 0.0468(9) -0.0014(7) 0.0002(9) -0.0026(8)
C7 0.0556(11) 0.0384(10) 0.0571(11) -0.0047(8) 0.0111(10) 0.0028(8)
C8 0.0567(12) 0.0432(10) 0.0547(11) 0.0007(9) 0.0124(10) -0.0050(9)
C11 0.0904(17) 0.0554(13) 0.0739(15) 0.0147(12) -0.0036(13) 0.0115(13)
O10 0.1226(16) 0.0367(8) 0.0961(13) -0.0117(8) 0.0322(12) 0.0084(10)
S9 0.0673(3) 0.0322(2) 0.0690(3) -0.0007(2) 0.0022(3) -0.0064(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.179(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.442(3) . ?
C3 C4 1.391(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) . ?
C6 S9 1.7928(18) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C11 S9 1.784(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O10 S9 1.4773(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 C1 H1 180.0 . . ?
C1 C2 C3 178.3(2) . . ?
C4 C3 C8 119.48(17) . . ?
C4 C3 C2 119.60(18) . . ?
C8 C3 C2 120.91(19) . . ?
C5 C4 C3 120.29(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.33(17) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 121.14(17) . . ?
C7 C6 S9 120.24(14) . . ?
C5 C6 S9 118.52(15) . . ?
C6 C7 C8 119.48(18) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C3 120.26(19) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
S9 C11 H11A 109.5 . . ?
S9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O10 S9 C11 106.40(13) . . ?
O10 S9 C6 108.00(9) . . ?
C11 S9 C6 97.10(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C5 -178.9(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C4 C5 C6 S9 -177.76(16) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
S9 C6 C7 C8 177.52(17) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C4 C3 C8 C7 -0.1(3) . . . . ?
C2 C3 C8 C7 178.7(2) . . . . ?
C7 C6 S9 O10 -6.9(2) . . . . ?
C5 C6 S9 O10 169.41(16) . . . . ?
C7 C6 S9 C11 103.00(18) . . . . ?
C5 C6 S9 C11 -80.73(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031

#=====================================================================
# END of data_Compound(S)1 CIF
#=====================================================================

#=====================================================================
data_Compound2
_database_code_depnum_ccdc_archive 'CCDC 253940'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 O2 S'
_chemical_formula_sum            'C9 H8 O2 S'
_chemical_formula_weight         180.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   22.1885(13)
_cell_length_b                   5.6567(5)
_cell_length_c                   14.0833(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1767.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      15.83
_cell_measurement_theta_max      18.71

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Nonius MACH3'
_diffrn_measurement_method       'theta/2theta scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2344
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.42
_reflns_number_total             1844
_reflns_number_gt                1547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'maXus (Gilmore et al, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL--97; PLATON'

_refine_special_details          
;
The absolute configuration was checked by refinement in SHELXL-97 using
TWIN and BASF to give 0.28834 for the enantiomer used, with
R1=0.0371 and wR2=0.1066. The other enantiomer refined to R1=0.0372
and wR2 0.1069.

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^)+(0.0520P)^2^+0.5622P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_chemical_absolute_configuration ad
_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   0.10(13)
_refine_ls_number_reflns         1844
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0208(2) 0.9437(11) 0.8374(5) 0.0658(15) Uani 1 1 d . . .
H1 H -0.0626 0.9416 0.8436 0.079 Uiso 1 1 calc R . .
C2 C 0.0310(2) 0.9463(10) 0.8296(4) 0.0548(13) Uani 1 1 d . . .
C3 C 0.09558(18) 0.9386(8) 0.8148(3) 0.0452(11) Uani 1 1 d . . .
C4 C 0.12056(19) 0.7617(8) 0.7621(4) 0.0523(11) Uani 1 1 d . . .
H4 H 0.0962 0.6428 0.7375 0.063 Uiso 1 1 calc R . .
C5 C 0.18222(19) 0.7582(8) 0.7447(4) 0.0532(13) Uani 1 1 d . . .
H5 H 0.1989 0.6364 0.7091 0.064 Uiso 1 1 calc R . .
C6 C 0.21818(18) 0.9318(8) 0.7796(3) 0.0432(12) Uani 1 1 d . . .
C7 C 0.1939(2) 1.1105(9) 0.8345(5) 0.0612(16) Uani 1 1 d . . .
H7 H 0.2186 1.2288 0.8586 0.073 Uiso 1 1 calc R . .
C8 C 0.1326(2) 1.1132(10) 0.8536(4) 0.0647(15) Uani 1 1 d . . .
H8 H 0.1163 1.2306 0.8919 0.078 Uiso 1 1 calc R . .
S9 S 0.29656(4) 0.9260(2) 0.75612(11) 0.0535(3) Uani 1 1 d . . .
O10 O 0.31212(15) 0.6855(6) 0.7349(4) 0.0758(14) Uani 1 1 d . . .
O11 O 0.32817(15) 1.0414(8) 0.8306(3) 0.0744(13) Uani 1 1 d . . .
C12 C 0.3040(2) 1.0946(11) 0.6510(5) 0.0686(17) Uani 1 1 d . . .
H12A H 0.2778 1.0317 0.6029 0.103 Uiso 1 1 calc R . .
H12B H 0.3450 1.0876 0.6292 0.103 Uiso 1 1 calc R . .
H12C H 0.2933 1.2560 0.6637 0.103 Uiso 1 1 calc R . .
C21 C 0.7664(2) 0.4279(10) 0.4919(4) 0.0636(16) Uani 1 1 d . . .
H21 H 0.8071 0.3916 0.4861 0.076 Uiso 1 1 calc R . .
C22 C 0.71456(19) 0.4740(9) 0.4993(4) 0.0528(13) Uani 1 1 d . . .
C23 C 0.65100(18) 0.5265(8) 0.5132(4) 0.0470(11) Uani 1 1 d . . .
C24 C 0.6072(2) 0.3725(9) 0.4810(4) 0.0589(14) Uani 1 1 d . . .
H24 H 0.6184 0.2380 0.4473 0.071 Uiso 1 1 calc R . .
C25 C 0.5464(2) 0.4173(9) 0.4986(4) 0.0595(15) Uani 1 1 d . . .
H25 H 0.5169 0.3137 0.4770 0.071 Uiso 1 1 calc R . .
C26 C 0.53068(17) 0.6176(7) 0.5486(3) 0.0418(12) Uani 1 1 d . . .
C27 C 0.57349(19) 0.7748(8) 0.5811(5) 0.0541(12) Uani 1 1 d . . .
H27 H 0.5620 0.9096 0.6143 0.065 Uiso 1 1 calc R . .
C28 C 0.63416(19) 0.7293(8) 0.5635(4) 0.0574(14) Uani 1 1 d . . .
H28 H 0.6635 0.8337 0.5852 0.069 Uiso 1 1 calc R . .
S29 S 0.45402(5) 0.6664(2) 0.57821(11) 0.0480(3) Uani 1 1 d . . .
O30 O 0.41681(13) 0.5551(7) 0.5069(3) 0.0688(11) Uani 1 1 d . . .
O31 O 0.44591(13) 0.9144(6) 0.5957(3) 0.0608(10) Uani 1 1 d . . .
C32 C 0.4461(2) 0.5105(10) 0.6835(4) 0.0656(16) Uani 1 1 d . . .
H32A H 0.4530 0.3454 0.6719 0.098 Uiso 1 1 calc R . .
H32B H 0.4061 0.5324 0.7078 0.098 Uiso 1 1 calc R . .
H32C H 0.4748 0.5674 0.7290 0.098 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
C1 0.045(3) 0.082(4) 0.070(4) -0.016(3) -0.005(3) 0.010(3)
C2 0.042(3) 0.067(3) 0.056(3) -0.006(3) -0.003(2) 0.006(2)
C3 0.036(2) 0.052(3) 0.048(3) 0.000(3) -0.003(2) 0.007(2)
C4 0.042(2) 0.052(3) 0.063(3) -0.013(3) -0.003(2) -0.004(2)
C5 0.047(2) 0.046(3) 0.067(3) -0.015(3) 0.005(3) 0.0068(19)
C6 0.036(2) 0.044(2) 0.049(3) -0.004(2) -0.008(2) 0.0058(19)
C7 0.046(3) 0.050(3) 0.089(4) -0.025(3) -0.008(3) 0.005(2)
C8 0.046(3) 0.068(3) 0.081(4) -0.026(3) -0.002(3) 0.012(2)
S9 0.0332(5) 0.0501(6) 0.0772(9) -0.0033(8) -0.0056(6) 0.0087(5)
O10 0.0497(18) 0.052(2) 0.125(4) -0.003(2) 0.004(2) 0.0148(15)
O11 0.043(2) 0.088(3) 0.092(3) -0.010(3) -0.020(2) 0.0036(19)
C12 0.044(2) 0.066(3) 0.096(5) 0.009(4) 0.005(3) 0.006(2)
C21 0.037(2) 0.078(4) 0.076(4) 0.014(3) 0.005(3) 0.003(2)
C22 0.044(3) 0.063(3) 0.052(3) 0.007(3) 0.001(2) -0.005(2)
C23 0.033(2) 0.054(3) 0.053(3) 0.007(3) 0.001(2) -0.0003(19)
C24 0.040(2) 0.056(3) 0.081(4) -0.019(3) 0.007(3) -0.002(2)
C25 0.033(2) 0.055(3) 0.090(4) -0.023(3) -0.004(3) -0.004(2)
C26 0.0280(18) 0.040(2) 0.057(3) -0.002(2) -0.0037(19) 0.0023(16)
C27 0.043(2) 0.048(2) 0.071(3) -0.018(3) -0.001(3) -0.0005(18)
C28 0.035(2) 0.056(3) 0.081(4) -0.009(3) -0.003(3) -0.0086(19)
S29 0.0307(4) 0.0453(6) 0.0680(7) -0.0046(7) -0.0031(6) 0.0067(4)
O30 0.0369(16) 0.077(2) 0.093(3) -0.017(2) -0.018(2) 0.0022(16)
O31 0.0517(17) 0.0443(16) 0.086(3) -0.002(2) 0.0033(19) 0.0127(14)
C32 0.043(3) 0.063(3) 0.091(5) 0.011(3) 0.018(3) 0.007(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.156(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.449(6) . ?
C3 C4 1.364(6) . ?
C3 C8 1.396(7) . ?
C4 C5 1.390(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.357(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(7) . ?
C6 S9 1.771(4) . ?
C7 C8 1.386(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
S9 O11 1.420(4) . ?
S9 O10 1.435(4) . ?
S9 C12 1.769(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C21 C22 1.183(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.455(6) . ?
C23 C24 1.381(7) . ?
C23 C28 1.399(7) . ?
C24 C25 1.396(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.379(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.379(6) . ?
C26 S29 1.773(4) . ?
C27 C28 1.393(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
S29 O31 1.436(3) . ?
S29 O30 1.445(4) . ?
S29 C32 1.734(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 180.0 . . ?
C1 C2 C3 176.2(6) . . ?
C4 C3 C8 119.5(4) . . ?
C4 C3 C2 120.2(4) . . ?
C8 C3 C2 120.3(4) . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 S9 119.8(4) . . ?
C7 C6 S9 120.1(4) . . ?
C6 C7 C8 119.9(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 119.6(5) . . ?
C7 C8 H8 120.2 . . ?
C3 C8 H8 120.2 . . ?
O11 S9 O10 118.1(3) . . ?
O11 S9 C12 108.9(3) . . ?
O10 S9 C12 108.3(3) . . ?
O11 S9 C6 109.8(2) . . ?
O10 S9 C6 107.0(2) . . ?
C12 S9 C6 103.8(2) . . ?
S9 C12 H12A 109.5 . . ?
S9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C22 C21 H21 180.0 . . ?
C21 C22 C23 177.1(6) . . ?
C24 C23 C28 119.7(4) . . ?
C24 C23 C22 120.6(5) . . ?
C28 C23 C22 119.6(4) . . ?
C23 C24 C25 120.5(5) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 119.0(4) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 121.7(4) . . ?
C25 C26 S29 119.4(3) . . ?
C27 C26 S29 118.8(3) . . ?
C26 C27 C28 119.2(4) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C27 C28 C23 120.0(4) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
O31 S29 O30 118.3(2) . . ?
O31 S29 C32 109.7(3) . . ?
O30 S29 C32 108.4(3) . . ?
O31 S29 C26 108.2(2) . . ?
O30 S29 C26 108.5(2) . . ?
C32 S29 C26 102.7(2) . . ?
S29 C32 H32A 109.5 . . ?
S29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
S29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 C5 -1.7(8) . . . . ?
C2 C3 C4 C5 177.6(5) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C4 C5 C6 C7 1.5(8) . . . . ?
C4 C5 C6 S9 -179.5(4) . . . . ?
C5 C6 C7 C8 -0.3(9) . . . . ?
S9 C6 C7 C8 -179.3(5) . . . . ?
C6 C7 C8 C3 -1.8(9) . . . . ?
C4 C3 C8 C7 2.8(9) . . . . ?
C2 C3 C8 C7 -176.5(5) . . . . ?
C5 C6 S9 O11 -152.1(4) . . . . ?
C7 C6 S9 O11 26.9(5) . . . . ?
C5 C6 S9 O10 -22.8(5) . . . . ?
C7 C6 S9 O10 156.2(5) . . . . ?
C5 C6 S9 C12 91.6(5) . . . . ?
C7 C6 S9 C12 -89.4(5) . . . . ?
C28 C23 C24 C25 -0.3(9) . . . . ?
C22 C23 C24 C25 176.8(5) . . . . ?
C23 C24 C25 C26 0.0(9) . . . . ?
C24 C25 C26 C27 0.4(9) . . . . ?
C24 C25 C26 S29 -175.9(5) . . . . ?
C25 C26 C27 C28 -0.5(9) . . . . ?
S29 C26 C27 C28 175.8(5) . . . . ?
C26 C27 C28 C23 0.2(9) . . . . ?
C24 C23 C28 C27 0.2(9) . . . . ?
C22 C23 C28 C27 -176.9(5) . . . . ?
C25 C26 S29 O31 -158.3(4) . . . . ?
C27 C26 S29 O31 25.4(5) . . . . ?
C25 C26 S29 O30 -28.8(5) . . . . ?
C27 C26 S29 O30 154.9(4) . . . . ?
C25 C26 S29 C32 85.7(5) . . . . ?
C27 C26 S29 C32 -90.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048

#=====================================================================
# END of data_Compound2 CIF
#=====================================================================

#=====================================================================
data_Compound3
_database_code_depnum_ccdc_archive 'CCDC 253941'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 O2 S'
_chemical_formula_sum            'C9 H8 O2 S'
_chemical_formula_weight         180.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.0507(10)
_cell_length_b                   9.6244(11)
_cell_length_c                   7.9662(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.273(10)
_cell_angle_gamma                90.00
_cell_volume                     437.91(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8.33
_cell_measurement_theta_max      15.31

_exptl_crystal_description       shard
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Nonius MACH3'
_diffrn_measurement_method       '/w-2/q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        50
_diffrn_reflns_number            926
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.42
_reflns_number_total             866
_reflns_number_gt                831
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'PLATON (Spek,2000)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek,2000)'
_computing_publication_material  'SHELXL--97; PLATON'

_refine_special_details          
;
The absolute configuration was checked by refinement in SHELXL-97 using
TWIN and BASF to give 0.02740 for the enantiomer used, with
R1=0.0562 and wR2=0.1476. The other enantiomer refined to R1=0.0563
and wR2 0.1480.

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^)+(0.1195P)^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
_chemical_absolute_configuration ad
_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   0.0(2)
_refine_ls_number_reflns         866
_refine_ls_number_parameters     110
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8906(10) 0.4229(8) 0.2361(7) 0.0525(15) Uani 1 1 d . . .
H1 H 0.9938 0.4878 0.2174 0.063 Uiso 1 1 calc R . .
C2 C 0.7584(8) 0.3398(5) 0.2600(6) 0.0405(12) Uani 1 1 d . . .
C3 C 0.6005(8) 0.2387(5) 0.2899(6) 0.0343(10) Uani 1 1 d . . .
C4 C 0.3763(8) 0.2129(5) 0.1675(6) 0.0317(9) Uani 1 1 d . . .
C5 C 0.2259(9) 0.1143(5) 0.2030(7) 0.0390(11) Uani 1 1 d . . .
H5 H 0.0782 0.0982 0.1208 0.047 Uiso 1 1 calc R . .
C6 C 0.3002(11) 0.0419(7) 0.3612(7) 0.0511(14) Uani 1 1 d . . .
H6 H 0.2019 -0.0233 0.3862 0.061 Uiso 1 1 calc R . .
C7 C 0.5211(13) 0.0659(8) 0.4833(8) 0.0520(15) Uani 1 1 d . . .
H7 H 0.5694 0.0163 0.5894 0.062 Uiso 1 1 calc R . .
C8 C 0.6697(9) 0.1620(7) 0.4497(7) 0.0479(13) Uani 1 1 d . . .
H8 H 0.8171 0.1764 0.5332 0.057 Uiso 1 1 calc R . .
S9 S 0.26886(16) 0.30877(11) -0.03385(13) 0.0343(4) Uani 1 1 d . . .
O10 O 0.2927(7) 0.4561(5) 0.0094(6) 0.0521(10) Uani 1 1 d . . .
O11 O 0.0367(7) 0.2578(5) -0.1290(5) 0.0491(10) Uani 1 1 d . . .
C12 C 0.4533(11) 0.2641(7) -0.1551(7) 0.0481(13) Uani 1 1 d . . .
H12A H 0.4641 0.1648 -0.1604 0.072 Uiso 1 1 calc R . .
H12B H 0.6063 0.3023 -0.0979 0.072 Uiso 1 1 calc R . .
H12C H 0.3904 0.3007 -0.2735 0.072 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
C1 0.036(3) 0.062(4) 0.057(3) -0.003(3) 0.012(2) -0.012(3)
C2 0.032(2) 0.047(3) 0.037(2) -0.007(2) 0.0029(17) 0.001(2)
C3 0.029(2) 0.035(3) 0.038(2) -0.0066(18) 0.0085(18) 0.0007(18)
C4 0.029(2) 0.034(2) 0.031(2) -0.0052(19) 0.0089(17) 0.0023(18)
C5 0.039(2) 0.037(3) 0.041(2) -0.002(2) 0.0136(19) -0.006(2)
C6 0.058(3) 0.049(3) 0.049(3) 0.003(3) 0.022(3) -0.009(3)
C7 0.065(4) 0.056(3) 0.032(3) 0.005(2) 0.013(2) -0.005(3)
C8 0.046(3) 0.057(3) 0.033(2) 0.000(2) 0.003(2) 0.005(3)
S9 0.0287(6) 0.0366(6) 0.0343(6) 0.0025(5) 0.0059(4) 0.0031(5)
O10 0.048(2) 0.044(2) 0.058(2) 0.002(2) 0.0085(17) 0.0079(18)
O11 0.0322(18) 0.061(2) 0.0444(19) 0.0025(17) -0.0011(15) -0.0018(17)
C12 0.052(3) 0.059(3) 0.038(2) 0.003(2) 0.020(2) 0.003(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.190(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.437(8) . ?
C3 C4 1.407(6) . ?
C3 C8 1.411(7) . ?
C4 C5 1.407(7) . ?
C4 S9 1.777(5) . ?
C5 C6 1.380(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(9) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
S9 O11 1.444(4) . ?
S9 O10 1.455(5) . ?
S9 C12 1.754(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 180.0 . . ?
C1 C2 C3 179.5(6) . . ?
C4 C3 C8 117.7(5) . . ?
C4 C3 C2 123.1(5) . . ?
C8 C3 C2 119.2(4) . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 S9 121.0(4) . . ?
C5 C4 S9 117.6(4) . . ?
C6 C5 C4 119.1(5) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 120.3(5) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C3 120.6(5) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
O11 S9 O10 117.3(3) . . ?
O11 S9 C12 108.3(3) . . ?
O10 S9 C12 109.8(3) . . ?
O11 S9 C4 107.5(2) . . ?
O10 S9 C4 108.3(2) . . ?
C12 S9 C4 105.1(3) . . ?
S9 C12 H12A 109.5 . . ?
S9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C3 C4 C5 0.1(7) . . . . ?
C2 C3 C4 C5 -179.1(5) . . . . ?
C8 C3 C4 S9 177.6(4) . . . . ?
C2 C3 C4 S9 -1.6(7) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
S9 C4 C5 C6 -177.5(4) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C5 C6 C7 C8 0.1(10) . . . . ?
C6 C7 C8 C3 0.1(10) . . . . ?
C4 C3 C8 C7 -0.2(8) . . . . ?
C2 C3 C8 C7 179.1(5) . . . . ?
C3 C4 S9 O11 180.0(4) . . . . ?
C5 C4 S9 O11 -2.4(4) . . . . ?
C3 C4 S9 O10 -52.5(4) . . . . ?
C5 C4 S9 O10 125.1(4) . . . . ?
C3 C4 S9 C12 64.8(5) . . . . ?
C5 C4 S9 C12 -117.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.42
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.154

#=====================================================================
# END of data_Compound3 CIF
#=====================================================================

#=====================================================================
data_Compound4
_database_code_depnum_ccdc_archive 'CCDC 649227'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O S'
_chemical_formula_sum            'C10 H10 O S'
_chemical_formula_weight         178.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.7881(4)
_cell_length_b                   7.9542(4)
_cell_length_c                   8.7386(4)
_cell_angle_alpha                94.048(5)
_cell_angle_beta                 92.037(6)
_cell_angle_gamma                95.872(7)
_cell_volume                     467.75(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      15.64
_cell_measurement_theta_max      18.83

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Nonius MACH3'
_diffrn_measurement_method       '\w-2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1813
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.33
_reflns_number_total             1695
_reflns_number_gt                1384
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'PLATON (Spek, 2000)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  'SHELXL--97; PLATON'

_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^)+(0.0601P)^2^+0.0947P] 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       0.073(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1695
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
S4 S 0.75783(9) 0.80716(7) 0.50969(6) 0.0533(2) Uani 1 1 d . . .
O11 O 0.9522(2) 0.23438(19) 0.08972(18) 0.0546(4) Uani 1 1 d . . .
C2 C 0.5525(3) 0.9178(3) 0.2647(3) 0.0477(5) Uani 1 1 d . . .
C10 C 1.0124(3) 0.6338(3) 0.3339(2) 0.0485(5) Uani 1 1 d . . .
H10 H 1.1097 0.7201 0.3691 0.058 Uiso 1 1 calc R . .
C9 C 1.0636(3) 0.5013(3) 0.2367(2) 0.0490(5) Uani 1 1 d . . .
H9 H 1.1934 0.4993 0.2066 0.059 Uiso 1 1 calc R . .
C8 C 0.9190(3) 0.3717(3) 0.1847(2) 0.0432(5) Uani 1 1 d . . .
C6 C 0.6763(3) 0.5096(3) 0.3265(2) 0.0473(5) Uani 1 1 d . . .
H6 H 0.5461 0.5116 0.3558 0.057 Uiso 1 1 calc R . .
C5 C 0.8197(3) 0.6408(3) 0.3801(2) 0.0433(5) Uani 1 1 d . . .
C3 C 0.7141(3) 0.9690(3) 0.3784(3) 0.0510(5) Uani 1 1 d . . .
H3A H 0.6845 1.0704 0.4378 0.061 Uiso 1 1 calc R . .
H3B H 0.8347 0.9975 0.3253 0.061 Uiso 1 1 calc R . .
C7 C 0.7261(3) 0.3769(3) 0.2302(3) 0.0491(5) Uani 1 1 d . . .
H7 H 0.6293 0.2900 0.1955 0.059 Uiso 1 1 calc R . .
C1 C 0.4236(4) 0.8764(3) 0.1735(3) 0.0594(6) Uani 1 1 d . . .
H1 H 0.3210 0.8435 0.1008 0.071 Uiso 1 1 calc R . .
C12 C 1.1490(4) 0.2222(3) 0.0406(3) 0.0599(6) Uani 1 1 d . . .
H12A H 1.1907 0.3188 -0.0148 0.090 Uiso 1 1 calc R . .
H12B H 1.1514 0.1205 -0.0251 0.090 Uiso 1 1 calc R . .
H12C H 1.2370 0.2192 0.1285 0.090 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
S4 0.0726(4) 0.0511(4) 0.0360(3) -0.0015(2) 0.0003(2) 0.0101(3)
O11 0.0578(10) 0.0488(9) 0.0563(9) -0.0073(7) 0.0031(7) 0.0087(7)
C2 0.0522(13) 0.0429(12) 0.0489(12) 0.0016(9) 0.0036(10) 0.0096(9)
C10 0.0478(12) 0.0472(12) 0.0481(12) -0.0001(9) -0.0051(9) -0.0024(9)
C9 0.0410(11) 0.0548(13) 0.0512(13) 0.0038(10) 0.0007(9) 0.0047(9)
C8 0.0505(12) 0.0400(11) 0.0392(11) 0.0039(8) -0.0012(9) 0.0063(9)
C6 0.0442(12) 0.0488(12) 0.0488(12) 0.0040(9) 0.0038(9) 0.0038(9)
C5 0.0528(13) 0.0419(11) 0.0356(10) 0.0051(8) -0.0019(9) 0.0068(9)
C3 0.0574(14) 0.0404(11) 0.0537(13) -0.0012(9) -0.0018(10) 0.0029(9)
C7 0.0490(12) 0.0428(11) 0.0528(12) -0.0006(9) 0.0002(10) -0.0043(9)
C1 0.0625(15) 0.0596(15) 0.0552(14) -0.0001(11) -0.0062(12) 0.0072(12)
C12 0.0656(15) 0.0623(15) 0.0550(14) 0.0008(11) 0.0082(11) 0.0221(12)

_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
S4 C5 1.774(2) . ?
S4 C3 1.823(2) . ?
O11 C8 1.367(2) . ?
O11 C12 1.428(3) . ?
C2 C1 1.168(3) . ?
C2 C3 1.460(3) . ?
C10 C9 1.386(3) . ?
C10 C5 1.388(3) . ?
C10 H10 0.9300 . ?
C9 C8 1.388(3) . ?
C9 H9 0.9300 . ?
C8 C7 1.386(3) . ?
C6 C7 1.380(3) . ?
C6 C5 1.396(3) . ?
C6 H6 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C7 H7 0.9300 . ?
C1 H1 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S4 C3 101.12(10) . . ?
C8 O11 C12 118.07(18) . . ?
C1 C2 C3 179.8(3) . . ?
C9 C10 C5 121.68(19) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
C10 C9 C8 119.3(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
O11 C8 C7 115.85(18) . . ?
O11 C8 C9 124.5(2) . . ?
C7 C8 C9 119.6(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C10 C5 C6 118.21(19) . . ?
C10 C5 S4 121.26(16) . . ?
C6 C5 S4 120.49(16) . . ?
C2 C3 S4 113.82(15) . . ?
C2 C3 H3A 108.8 . . ?
S4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
S4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C6 C7 C8 120.69(19) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C2 C1 H1 180.0 . . ?
O11 C12 H12A 109.5 . . ?
O11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C10 C9 C8 -0.4(3) . . . . ?
C12 O11 C8 C7 -179.46(18) . . . . ?
C12 O11 C8 C9 0.2(3) . . . . ?
C10 C9 C8 O11 -179.47(19) . . . . ?
C10 C9 C8 C7 0.2(3) . . . . ?
C9 C10 C5 C6 0.3(3) . . . . ?
C9 C10 C5 S4 177.83(17) . . . . ?
C7 C6 C5 C10 0.0(3) . . . . ?
C7 C6 C5 S4 -177.55(16) . . . . ?
C3 S4 C5 C10 85.60(18) . . . . ?
C3 S4 C5 C6 -96.91(18) . . . . ?
C5 S4 C3 C2 61.19(18) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
O11 C8 C7 C6 179.79(19) . . . . ?
C9 C8 C7 C6 0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044

#=====================================================================
# END of data_Compound4 CIF
#=====================================================================

#=====================================================================
data_Compound5
_database_code_depnum_ccdc_archive 'CCDC 649228'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O2 S'
_chemical_formula_sum            'C10 H10 O2 S'
_chemical_formula_weight         194.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.5942(7)
_cell_length_b                   7.9196(3)
_cell_length_c                   11.5721(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.590(4)
_cell_angle_gamma                90.00
_cell_volume                     960.03(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.74
_cell_measurement_theta_max      13.92

_exptl_crystal_description       needles
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius MACH3'
_diffrn_measurement_method       '\w-2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1875
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.49
_reflns_number_total             1777
_reflns_number_gt                1468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'maXus (Gilmoreet al, 1998)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL--97; PLATON'

_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^)+(0.0563P)^2^+0.2901P] 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         1777
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4596(3) 0.2051(5) 0.4993(2) 0.0847(9) Uani 1 1 d . . .
H1 H 0.4266 0.1426 0.4336 0.102 Uiso 1 1 calc R . .
C2 C 0.5010(2) 0.2837(3) 0.58182(19) 0.0547(5) Uani 1 1 d . . .
C3 C 0.5496(2) 0.3767(3) 0.68617(19) 0.0526(5) Uani 1 1 d . . .
H3A H 0.4789 0.4321 0.7152 0.063 Uiso 1 1 calc R . .
H3B H 0.6070 0.4638 0.6663 0.063 Uiso 1 1 calc R . .
S4 S 0.63426(4) 0.24523(7) 0.80233(4) 0.0507(2) Uani 1 1 d . . .
O5 O 0.72740(15) 0.1428(2) 0.74783(16) 0.0725(5) Uani 1 1 d . . .
C6 C 0.50723(17) 0.1050(2) 0.82385(15) 0.0411(4) Uani 1 1 d . . .
C7 C 0.5174(2) -0.0648(3) 0.79934(17) 0.0506(5) Uani 1 1 d . . .
H7 H 0.5873 -0.1045 0.7675 0.061 Uiso 1 1 calc R . .
C8 C 0.4237(2) -0.1753(3) 0.8221(2) 0.0597(6) Uani 1 1 d . . .
H8 H 0.4299 -0.2895 0.8051 0.072 Uiso 1 1 calc R . .
C9 C 0.3208(2) -0.1163(3) 0.8701(2) 0.0591(6) Uani 1 1 d . . .
H9 H 0.2574 -0.1912 0.8844 0.071 Uiso 1 1 calc R . .
C10 C 0.31033(19) 0.0533(3) 0.89759(18) 0.0512(5) Uani 1 1 d . . .
H10 H 0.2405 0.0918 0.9302 0.061 Uiso 1 1 calc R . .
C11 C 0.40493(17) 0.1647(2) 0.87592(15) 0.0416(4) Uani 1 1 d . . .
O12 O 0.40788(14) 0.33269(18) 0.90080(13) 0.0539(4) Uani 1 1 d . . .
C13 C 0.3125(2) 0.3993(3) 0.9635(2) 0.0665(7) Uani 1 1 d . . .
H13A H 0.2304 0.3919 0.9158 0.100 Uiso 1 1 calc R . .
H13B H 0.3315 0.5154 0.9829 0.100 Uiso 1 1 calc R . .
H13C H 0.3117 0.3355 1.0339 0.100 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
C1 0.0827(19) 0.117(2) 0.0526(14) -0.0114(16) 0.0058(14) 0.0170(18)
C2 0.0493(12) 0.0670(13) 0.0495(12) 0.0079(11) 0.0133(9) 0.0091(10)
C3 0.0465(11) 0.0472(11) 0.0655(13) 0.0039(10) 0.0134(9) -0.0022(9)
S4 0.0343(3) 0.0655(4) 0.0522(3) -0.0019(2) 0.0064(2) -0.0012(2)
O5 0.0457(9) 0.0925(13) 0.0846(11) 0.0169(10) 0.0274(8) 0.0222(8)
C6 0.0374(10) 0.0477(11) 0.0379(9) -0.0014(8) 0.0050(7) 0.0051(8)
C7 0.0530(12) 0.0534(12) 0.0447(11) -0.0075(9) 0.0050(9) 0.0122(10)
C8 0.0734(16) 0.0411(11) 0.0614(13) -0.0056(10) -0.0002(11) 0.0030(11)
C9 0.0586(13) 0.0522(13) 0.0645(13) 0.0060(11) 0.0018(11) -0.0097(10)
C10 0.0437(11) 0.0584(12) 0.0531(11) 0.0027(10) 0.0126(9) 0.0003(9)
C11 0.0422(10) 0.0433(11) 0.0394(9) -0.0032(8) 0.0066(8) 0.0029(8)
O12 0.0557(9) 0.0456(8) 0.0655(9) -0.0111(7) 0.0252(7) 0.0014(7)
C13 0.0699(15) 0.0639(14) 0.0707(15) -0.0141(12) 0.0273(12) 0.0144(12)

_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
C1 C2 1.169(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.442(3) . ?
C3 S4 1.826(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
S4 O5 1.4884(16) . ?
S4 C6 1.791(2) . ?
C6 C7 1.382(3) . ?
C6 C11 1.399(2) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 O12 1.360(2) . ?
O12 C13 1.430(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 180.0 . . ?
C1 C2 C3 177.9(3) . . ?
C2 C3 S4 113.56(15) . . ?
C2 C3 H3A 108.9 . . ?
S4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
S4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O5 S4 C6 106.30(10) . . ?
O5 S4 C3 106.42(10) . . ?
C6 S4 C3 99.15(9) . . ?
C7 C6 C11 120.42(19) . . ?
C7 C6 S4 119.46(15) . . ?
C11 C6 S4 119.81(14) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
O12 C11 C10 125.33(17) . . ?
O12 C11 C6 115.28(17) . . ?
C10 C11 C6 119.39(18) . . ?
C11 O12 C13 118.21(16) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 S4 O5 49.61(18) . . . . ?
C2 C3 S4 C6 -60.50(16) . . . . ?
O5 S4 C6 C7 5.31(19) . . . . ?
C3 S4 C6 C7 115.51(17) . . . . ?
O5 S4 C6 C11 179.00(15) . . . . ?
C3 S4 C6 C11 -70.79(16) . . . . ?
C11 C6 C7 C8 2.5(3) . . . . ?
S4 C6 C7 C8 176.16(15) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 O12 -178.51(19) . . . . ?
C9 C10 C11 C6 1.8(3) . . . . ?
C7 C6 C11 O12 177.14(17) . . . . ?
S4 C6 C11 O12 3.5(2) . . . . ?
C7 C6 C11 C10 -3.1(3) . . . . ?
S4 C6 C11 C10 -176.76(14) . . . . ?
C10 C11 O12 C13 5.8(3) . . . . ?
C6 C11 O12 C13 -174.49(18) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.050

#=====================================================================
# END of data_Compound5 CIF
#=====================================================================

#=====================================================================
data_Compound6
_database_code_depnum_ccdc_archive 'CCDC 649229'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O3 S'
_chemical_formula_sum            'C10 H10 O3 S'
_chemical_formula_weight         210.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.9083(4)
_cell_length_b                   8.8890(4)
_cell_length_c                   14.4521(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1015.94(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.86
_cell_measurement_theta_max      14.21

_exptl_crystal_description       needles
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '\w-2\q scans'
_diffrn_measurement_method       'Nonius MACH3'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2570
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.47
_reflns_number_total             1894
_reflns_number_gt                1738
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'maXus (Gilmore et al, 1998)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  'SHELXL--97; PLATON'

_refine_special_details          
;
The absolute configuration was checked by refinement in SHELXL-97 using
TWIN and BASF to give 0.00001 for the enantiomer used, with
R1=0.029 and wR2=0.077. The other enantiomer refined to R1=0.030
and wR2 0.079.

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^)+(0.0286P)^2^+0.3126P] 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       0.0118(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1894
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0766
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7063(4) 0.8837(3) -0.13385(16) 0.0560(6) Uani 1 1 d . . .
H1 H 0.6343 0.8719 -0.1842 0.067 Uiso 1 1 calc R . .
C2 C 0.7971(3) 0.8987(3) -0.07028(15) 0.0456(5) Uani 1 1 d . . .
C3 C 0.9097(3) 0.9151(3) 0.00886(16) 0.0473(6) Uani 1 1 d . . .
H3A H 0.9528 1.0172 0.0104 0.057 Uiso 1 1 calc R . .
H3B H 1.0052 0.8477 0.0014 0.057 Uiso 1 1 calc R . .
S4 S 0.80680(7) 0.87481(6) 0.11634(4) 0.03925(15) Uani 1 1 d . . .
O5 O 0.7314(2) 0.72835(17) 0.10898(13) 0.0544(4) Uani 1 1 d . . .
O6 O 0.9292(2) 0.9003(2) 0.18808(11) 0.0533(5) Uani 1 1 d . . .
C7 C 0.6411(2) 1.0073(2) 0.12664(15) 0.0359(5) Uani 1 1 d . . .
C8 C 0.4786(3) 0.9544(3) 0.13990(15) 0.0458(6) Uani 1 1 d . . .
H8 H 0.4579 0.8514 0.1393 0.055 Uiso 1 1 calc R . .
C9 C 0.3469(3) 1.0537(4) 0.15397(19) 0.0600(8) Uani 1 1 d . . .
H9 H 0.2374 1.0182 0.1624 0.072 Uiso 1 1 calc R . .
C10 C 0.3795(4) 1.2059(4) 0.1554(2) 0.0632(8) Uani 1 1 d . . .
H10 H 0.2911 1.2728 0.1658 0.076 Uiso 1 1 calc R . .
C11 C 0.5399(4) 1.2608(3) 0.14164(17) 0.0541(7) Uani 1 1 d . . .
H11 H 0.5588 1.3641 0.1422 0.065 Uiso 1 1 calc R . .
C12 C 0.6736(3) 1.1629(2) 0.12689(15) 0.0418(5) Uani 1 1 d . . .
O13 O 0.8363(2) 1.20520(17) 0.11329(15) 0.0577(5) Uani 1 1 d . . .
C14 C 0.8743(4) 1.3630(3) 0.1054(2) 0.0707(8) Uani 1 1 d . . .
H14A H 0.8065 1.4065 0.0573 0.106 Uiso 1 1 calc R . .
H14B H 0.9918 1.3755 0.0907 0.106 Uiso 1 1 calc R . .
H14C H 0.8500 1.4121 0.1631 0.106 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
C1 0.0631(15) 0.0583(14) 0.0466(14) -0.0013(12) 0.0002(13) 0.0125(15)
C2 0.0534(13) 0.0403(12) 0.0430(12) -0.0009(10) 0.0095(12) 0.0093(13)
C3 0.0440(14) 0.0527(14) 0.0453(13) -0.0047(11) 0.0095(11) 0.0029(11)
S4 0.0406(3) 0.0379(3) 0.0393(3) -0.0015(3) 0.0002(3) 0.0023(3)
O5 0.0677(11) 0.0351(8) 0.0603(10) 0.0013(8) 0.0003(10) -0.0013(8)
O6 0.0490(10) 0.0638(11) 0.0471(9) -0.0048(8) -0.0069(8) 0.0069(9)
C7 0.0365(10) 0.0386(11) 0.0325(11) -0.0049(10) -0.0008(10) 0.0005(9)
C8 0.0433(12) 0.0522(13) 0.0420(14) -0.0002(10) 0.0025(10) -0.0078(11)
C9 0.0375(13) 0.093(2) 0.0493(14) -0.0007(14) 0.0043(11) 0.0024(14)
C10 0.0581(17) 0.079(2) 0.0521(15) -0.0032(15) 0.0023(13) 0.0271(16)
C11 0.0712(17) 0.0446(13) 0.0465(15) -0.0044(11) -0.0052(13) 0.0140(13)
C12 0.0474(13) 0.0399(12) 0.0382(11) -0.0034(10) -0.0026(12) -0.0004(10)
O13 0.0532(10) 0.0384(8) 0.0814(12) -0.0031(10) 0.0017(11) -0.0136(8)
C14 0.093(2) 0.0430(13) 0.0761(18) 0.0008(15) -0.0066(18) -0.0238(14)

_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
C1 C2 1.174(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.457(4) . ?
C3 S4 1.790(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
S4 O5 1.4360(16) . ?
S4 O6 1.4364(17) . ?
S4 C7 1.768(2) . ?
C7 C8 1.382(3) . ?
C7 C12 1.407(3) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 O13 1.355(3) . ?
O13 C14 1.439(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 180.0 . . ?
C1 C2 C3 179.2(3) . . ?
C2 C3 S4 112.56(17) . . ?
C2 C3 H3A 109.1 . . ?
S4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
S4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O5 S4 O6 118.46(11) . . ?
O5 S4 C7 107.60(10) . . ?
O6 S4 C7 109.46(10) . . ?
O5 S4 C3 107.82(11) . . ?
O6 S4 C3 106.78(11) . . ?
C7 S4 C3 106.06(11) . . ?
C8 C7 C12 120.3(2) . . ?
C8 C7 S4 118.28(17) . . ?
C12 C7 S4 121.34(16) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O13 C12 C11 124.9(2) . . ?
O13 C12 C7 116.46(19) . . ?
C11 C12 C7 118.6(2) . . ?
C12 O13 C14 118.7(2) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 S4 O5 53.7(2) . . . . ?
C2 C3 S4 O6 -177.98(17) . . . . ?
C2 C3 S4 C7 -61.3(2) . . . . ?
O5 S4 C7 C8 9.4(2) . . . . ?
O6 S4 C7 C8 -120.58(19) . . . . ?
C3 S4 C7 C8 124.57(19) . . . . ?
O5 S4 C7 C12 -174.29(19) . . . . ?
O6 S4 C7 C12 55.7(2) . . . . ?
C3 S4 C7 C12 -59.1(2) . . . . ?
C12 C7 C8 C9 -0.3(4) . . . . ?
S4 C7 C8 C9 176.02(19) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 O13 -179.5(2) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C8 C7 C12 O13 -179.9(2) . . . . ?
S4 C7 C12 O13 3.8(3) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
S4 C7 C12 C11 -175.56(18) . . . . ?
C11 C12 O13 C14 -5.6(4) . . . . ?
C7 C12 O13 C14 175.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.47
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.032

#=====================================================================
# END of data_Compound6 CIF
#=====================================================================

#=====================================================================
data_Compound7
_database_code_depnum_ccdc_archive 'CCDC 649230'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 F O2 S'
_chemical_formula_sum            'C9 H7 F O2 S'
_chemical_formula_weight         198.21

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.3890(10)
_cell_length_b                   8.134(3)
_cell_length_c                   8.474(2)
_cell_angle_alpha                109.23(2)
_cell_angle_beta                 98.60(2)
_cell_angle_gamma                106.01(2)
_cell_volume                     445.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      5.85
_cell_measurement_theta_max      17.20

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             204
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Nonius MACH3'
_diffrn_measurement_method       '\w-2\q scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        20
_diffrn_reflns_number            1773
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.47
_reflns_number_total             1650
_reflns_number_gt                950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius MACH3'
_computing_cell_refinement       'Nonius MACH3'
_computing_data_reduction        'PLATON (Spek,2000)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek,2000)'
_computing_publication_material  'SHELXL--97; PLATON'

_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^)+(0.1639P)^2^+1.1172P] 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         1650
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1602
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.3204
_refine_ls_wR_factor_gt          0.2340
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5797(14) 0.7950(13) 0.5001(12) 0.073(3) Uani 1 1 d . . .
H1 H 0.6555 0.8292 0.4302 0.087 Uiso 1 1 calc R . .
C2 C 0.4848(11) 0.7521(11) 0.5878(11) 0.0566(19) Uani 1 1 d . . .
C3 C 0.3638(12) 0.7081(11) 0.6996(10) 0.057(2) Uani 1 1 d . . .
H3A H 0.4466 0.7299 0.8100 0.068 Uiso 1 1 calc R . .
H3B H 0.2822 0.5778 0.6464 0.068 Uiso 1 1 calc R . .
S4 S 0.2149(3) 0.8461(3) 0.7341(3) 0.0621(8) Uani 1 1 d . . .
O5 O 0.0871(10) 0.8002(13) 0.5722(9) 0.105(3) Uani 1 1 d . . .
O6 O 0.3431(11) 1.0343(9) 0.8313(10) 0.089(2) Uani 1 1 d . . .
C7 C 0.0783(7) 0.7742(7) 0.8642(6) 0.0489(18) Uani 1 1 d G . .
C8 C 0.1541(6) 0.8494(7) 1.0431(6) 0.062(2) Uani 1 1 d G . .
H8 H 0.2789 0.9380 1.0934 0.074 Uiso 1 1 calc R . .
C9 C 0.0434(8) 0.7923(8) 1.1468(5) 0.068(2) Uani 1 1 d G . .
H9 H 0.0941 0.8427 1.2665 0.082 Uiso 1 1 calc R . .
C10 C -0.1431(7) 0.6599(7) 1.0717(7) 0.0530(19) Uani 1 1 d G . .
C11 C -0.2190(6) 0.5847(7) 0.8928(7) 0.069(2) Uani 1 1 d G . .
H11 H -0.3438 0.4961 0.8425 0.083 Uiso 1 1 calc R . .
C12 C -0.1083(7) 0.6418(8) 0.7891(5) 0.070(2) Uani 1 1 d G . .
H12 H -0.1590 0.5914 0.6694 0.085 Uiso 1 1 calc R . .
F13 F -0.2509(8) 0.6083(7) 1.1669(7) 0.0808(16) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.080(6) 0.079(6) 0.073(6) 0.036(5) 0.047(5) 0.025(5)
C2 0.054(4) 0.054(5) 0.059(5) 0.015(4) 0.023(4) 0.016(4)
C3 0.068(5) 0.051(4) 0.056(5) 0.022(4) 0.028(4) 0.018(4)
S4 0.0688(14) 0.0885(17) 0.0673(14) 0.0536(13) 0.0420(11) 0.0432(12)
O5 0.087(5) 0.208(9) 0.083(5) 0.099(6) 0.049(4) 0.078(5)
O6 0.109(5) 0.066(4) 0.140(6) 0.064(4) 0.085(5) 0.043(4)
C7 0.055(4) 0.057(5) 0.053(4) 0.028(4) 0.033(4) 0.029(4)
C8 0.056(5) 0.071(5) 0.048(5) 0.020(4) 0.019(4) 0.006(4)
C9 0.082(6) 0.080(6) 0.052(5) 0.031(5) 0.035(5) 0.025(5)
C10 0.055(4) 0.051(4) 0.075(5) 0.033(4) 0.039(4) 0.029(4)
C11 0.046(4) 0.084(6) 0.074(6) 0.035(5) 0.016(4) 0.014(4)
C12 0.055(5) 0.094(7) 0.051(5) 0.019(5) 0.011(4) 0.023(5)
F13 0.084(3) 0.085(3) 0.103(4) 0.056(3) 0.063(3) 0.031(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
C1 C2 1.165(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.457(10) . ?
C3 S4 1.766(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
S4 O5 1.413(7) . ?
S4 O6 1.433(7) . ?
S4 C7 1.735(4) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 F13 1.301(5) . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 180.0 . . ?
C1 C2 C3 176.8(9) . . ?
C2 C3 S4 110.6(6) . . ?
C2 C3 H3A 109.5 . . ?
S4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
S4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
O5 S4 O6 119.5(5) . . ?
O5 S4 C7 108.5(3) . . ?
O6 S4 C7 108.6(3) . . ?
O5 S4 C3 107.7(4) . . ?
O6 S4 C3 106.8(4) . . ?
C7 S4 C3 104.9(3) . . ?
C8 C7 C12 120.0 . . ?
C8 C7 S4 120.2(3) . . ?
C12 C7 S4 119.8(3) . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
F13 C10 C9 120.9(5) . . ?
F13 C10 C11 119.1(5) . . ?
C9 C10 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 S4 O5 63.4(7) . . . . ?
C2 C3 S4 O6 -66.0(7) . . . . ?
C2 C3 S4 C7 178.8(6) . . . . ?
O5 S4 C7 C8 -160.3(5) . . . . ?
O6 S4 C7 C8 -29.1(5) . . . . ?
C3 S4 C7 C8 84.8(4) . . . . ?
O5 S4 C7 C12 19.2(5) . . . . ?
O6 S4 C7 C12 150.4(4) . . . . ?
C3 S4 C7 C12 -95.7(4) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
S4 C7 C8 C9 179.5(4) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 F13 -178.2(5) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
F13 C10 C11 C12 178.2(5) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
S4 C7 C12 C11 -179.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.112

#=====================================================================
# END of data_Compound7 CIF
#=====================================================================

#=====================================================================
data_Compound8
_database_code_depnum_ccdc_archive 'CCDC 649231'
#=====================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 O3 S'
_chemical_formula_sum            'C11 H12 O3 S'
_chemical_formula_weight         224.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   6.5860(2)
_cell_length_b                   10.1867(3)
_cell_length_c                   16.9358(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1136.22(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    4794
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)

The 0 2 0 reflection has been omitted due to the
beamstop.
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6747
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1514
_reflns_number_gt                1333
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  'SHELXL-97; PLATON'

_refine_special_details          
;
The absolute configuration was not determined reliably, 1056 Friedel
pairs were averaged for the refinement.

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^)+(0.0375P)^2^+0.2329P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_chemical_absolute_configuration unk
_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   0.47(11)
_refine_ls_number_reflns         1514
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1446(5) 0.7755(3) 0.03797(17) 0.0555(7) Uani 1 1 d . . .
H1 H 1.1666 0.6884 0.0219 0.067 Uiso 1 1 calc R . .
C2 C 1.1171(4) 0.8840(2) 0.05792(15) 0.0410(6) Uani 1 1 d . . .
C3 C 1.0949(4) 1.0222(2) 0.07976(14) 0.0365(5) Uani 1 1 d . . .
H3 H 1.1737 1.0382 0.1286 0.044 Uiso 1 1 calc R . .
C4 C 1.1720(5) 1.1151(3) 0.01568(15) 0.0536(7) Uani 1 1 d . . .
H4A H 1.1037 1.0958 -0.0337 0.080 Uiso 1 1 calc R . .
H4B H 1.3172 1.1033 0.0091 0.080 Uiso 1 1 calc R . .
H4C H 1.1442 1.2051 0.0310 0.080 Uiso 1 1 calc R . .
S5 S 0.83153(9) 1.06115(5) 0.09878(3) 0.03469(16) Uani 1 1 d . . .
O6 O 0.7140(3) 1.02601(17) 0.03031(10) 0.0448(5) Uani 1 1 d . . .
O7 O 0.8267(3) 1.19572(15) 0.12411(10) 0.0459(4) Uani 1 1 d . . .
C8 C 0.7518(4) 0.9602(2) 0.17743(13) 0.0366(5) Uani 1 1 d . . .
C9 C 0.5789(4) 0.8833(3) 0.16656(17) 0.0471(6) Uani 1 1 d . . .
H9 H 0.5154 0.8803 0.1169 0.057 Uiso 1 1 calc R . .
C10 C 0.5010(5) 0.8116(3) 0.22882(18) 0.0610(8) Uani 1 1 d . . .
H10 H 0.3830 0.7609 0.2221 0.073 Uiso 1 1 calc R . .
C11 C 0.5977(5) 0.8151(3) 0.30067(19) 0.0636(9) Uani 1 1 d . . .
H11 H 0.5449 0.7658 0.3429 0.076 Uiso 1 1 calc R . .
C12 C 0.7698(5) 0.8890(3) 0.31240(16) 0.0578(8) Uani 1 1 d . . .
H12 H 0.8336 0.8892 0.3620 0.069 Uiso 1 1 calc R . .
C13 C 0.8496(4) 0.9634(2) 0.25094(14) 0.0429(6) Uani 1 1 d . . .
O14 O 1.0160(3) 1.03992(19) 0.25668(10) 0.0550(5) Uani 1 1 d . . .
C15 C 1.1284(6) 1.0381(3) 0.32946(15) 0.0659(9) Uani 1 1 d . . .
H15A H 1.1717 0.9490 0.3408 0.099 Uiso 1 1 calc R . .
H15B H 1.0427 1.0696 0.3720 0.099 Uiso 1 1 calc R . .
H15C H 1.2465 1.0944 0.3247 0.099 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
C1 0.0449(16) 0.0448(14) 0.0769(19) -0.0113(13) 0.0046(16) 0.0050(13)
C2 0.0318(13) 0.0450(13) 0.0461(13) -0.0013(11) 0.0035(11) 0.0033(10)
C3 0.0312(11) 0.0390(12) 0.0393(13) -0.0017(9) 0.0021(10) 0.0013(10)
C4 0.0539(16) 0.0533(14) 0.0535(15) 0.0061(12) 0.0145(17) -0.0022(15)
S5 0.0330(3) 0.0346(3) 0.0364(3) 0.0026(2) 0.0009(3) 0.0050(2)
O6 0.0413(11) 0.0522(10) 0.0409(8) 0.0045(7) -0.0069(8) 0.0021(8)
O7 0.0516(10) 0.0330(8) 0.0530(10) 0.0004(7) 0.0049(10) 0.0089(8)
C8 0.0320(11) 0.0388(12) 0.0390(12) 0.0042(10) 0.0061(10) 0.0039(11)
C9 0.0326(13) 0.0526(14) 0.0561(15) 0.0026(13) 0.0030(13) 0.0002(12)
C10 0.0395(15) 0.0649(18) 0.079(2) 0.0107(17) 0.0147(17) -0.0066(15)
C11 0.059(2) 0.0677(19) 0.0638(18) 0.0213(16) 0.0196(17) -0.0027(17)
C12 0.0620(19) 0.0657(17) 0.0459(15) 0.0154(13) 0.0078(15) 0.0047(15)
C13 0.0429(14) 0.0442(13) 0.0416(12) 0.0057(10) 0.0049(12) 0.0028(13)
O14 0.0597(12) 0.0652(12) 0.0400(9) 0.0096(9) -0.0095(9) -0.0153(12)
C15 0.078(2) 0.0752(19) 0.0446(15) -0.0005(14) -0.0172(16) -0.0101(19)

_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
C1 C2 1.170(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.462(3) . ?
C3 C4 1.527(3) . ?
C3 S5 1.809(2) . ?
C3 H3 0.9900 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
S5 O7 1.4368(16) . ?
S5 O6 1.4393(17) . ?
S5 C8 1.763(2) . ?
C8 C9 1.394(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.375(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9400 . ?
C13 O14 1.348(3) . ?
O14 C15 1.438(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 180.0 . . ?
C1 C2 C3 176.1(3) . . ?
C2 C3 C4 112.5(2) . . ?
C2 C3 S5 110.61(18) . . ?
C4 C3 S5 108.04(18) . . ?
C2 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
S5 C3 H3 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O7 S5 O6 117.77(11) . . ?
O7 S5 C8 108.94(11) . . ?
O6 S5 C8 107.68(11) . . ?
O7 S5 C3 106.49(12) . . ?
O6 S5 C3 108.52(11) . . ?
C8 S5 C3 106.98(11) . . ?
C9 C8 C13 120.4(2) . . ?
C9 C8 S5 118.10(19) . . ?
C13 C8 S5 121.36(19) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O14 C13 C12 124.6(3) . . ?
O14 C13 C8 116.8(2) . . ?
C12 C13 C8 118.6(3) . . ?
C13 O14 C15 118.2(2) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 S5 O7 176.68(17) . . . . ?
C4 C3 S5 O7 -59.72(18) . . . . ?
C2 C3 S5 O6 -55.6(2) . . . . ?
C4 C3 S5 O6 67.98(18) . . . . ?
C2 C3 S5 C8 60.3(2) . . . . ?
C4 C3 S5 C8 -176.10(17) . . . . ?
O7 S5 C8 C9 119.0(2) . . . . ?
O6 S5 C8 C9 -9.8(2) . . . . ?
C3 S5 C8 C9 -126.3(2) . . . . ?
O7 S5 C8 C13 -56.4(2) . . . . ?
O6 S5 C8 C13 174.8(2) . . . . ?
C3 S5 C8 C13 58.3(2) . . . . ?
C13 C8 C9 C10 1.1(4) . . . . ?
S5 C8 C9 C10 -174.4(2) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C11 C12 C13 O14 179.3(3) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C9 C8 C13 O14 179.9(2) . . . . ?
S5 C8 C13 O14 -4.8(3) . . . . ?
C9 C8 C13 C12 -0.3(4) . . . . ?
S5 C8 C13 C12 175.1(2) . . . . ?
C12 C13 O14 C15 4.6(4) . . . . ?
C8 C13 O14 C15 -175.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.055

#=====================================================================
# END of data_Compound8 CIF
#=====================================================================


