# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof Tayur Guru Row'
_publ_contact_author_email       SSCTNG@SSCU.IISC.ERNET.IN

_publ_section_title              
;
Evaluation of Intermolecular interactions in
thioisocoumarin derivatives: The role of sulphur atom in generating
packing motifs
;
loop_
_publ_author_name
'T.N. Guru Row'
'Venkatesha R. Hathwar'
'F. Nawaz Khan'
'P. Manivel'

# Attachment 'TI-1.cif'

data_chsic_m
_database_code_depnum_ccdc_archive 'CCDC 656918'
#==============================================================================

_audit_creation_date             'Aug 08 00:02:31 2008'
_audit_creation_method           ' SHELXL-97'
_audit_update_record             
;
;

_chemical_name_systematic        
;
;
_chemical_name_common            3-Cyclohexyl-1H-isochromene-1-thione
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 O S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H16 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         244.35
_chemical_compound_source        'see text'

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

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.9463(14)
_cell_length_b                   12.335(2)
_cell_length_c                   12.338(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.704(3)
_cell_angle_gamma                90
_cell_volume                     1310.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.32
_cell_special_details            
; ?
;

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16

_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.228
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
# Example: '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9161
_exptl_absorpt_correction_T_max  0.9644

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

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_reflns_number            10010
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.50

_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

_reflns_number_total             2570
_reflns_number_gt                1640
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_cell_refinement       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT V6.45a, (Bruker, 2004)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     218
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.01784(8) 0.53284(6) 0.29523(6) 0.0873(3) Uani 1 1 d . . .
O1 O 0.15208(15) 0.40566(11) 0.18893(10) 0.0591(4) Uani 1 1 d . . .
C1 C 0.1084(2) 0.50996(17) 0.19872(18) 0.0601(6) Uani 1 1 d . . .
C2 C 0.2237(2) 0.37076(16) 0.10901(15) 0.0508(5) Uani 1 1 d . . .
C3 C 0.2524(2) 0.44076(18) 0.03538(17) 0.0596(6) Uani 1 1 d D . .
C4 C 0.2485(3) 0.6294(2) -0.0352(2) 0.0827(8) Uani 1 1 d D . .
C5 C 0.2159(4) 0.7367(3) -0.0249(3) 0.1026(10) Uani 1 1 d D . .
C6 C 0.1482(4) 0.7714(2) 0.0574(3) 0.1024(10) Uani 1 1 d D . .
C7 C 0.1123(3) 0.6991(2) 0.1312(3) 0.0827(7) Uani 1 1 d D . .
C8 C 0.1454(2) 0.58805(17) 0.12258(17) 0.0619(6) Uani 1 1 d . . .
C9 C 0.2153(2) 0.55305(18) 0.03960(18) 0.0629(6) Uani 1 1 d . . .
C10 C 0.2603(2) 0.25314(15) 0.12480(14) 0.0500(5) Uani 1 1 d D . .
C11 C 0.3846(3) 0.23255(19) 0.23504(16) 0.0656(6) Uani 1 1 d D . .
C12 C 0.4129(3) 0.1122(2) 0.25559(19) 0.0727(7) Uani 1 1 d D . .
C13 C 0.4587(3) 0.0590(2) 0.1584(2) 0.0809(7) Uani 1 1 d D . .
C14 C 0.3363(3) 0.0800(2) 0.0484(2) 0.0789(7) Uani 1 1 d D . .
C15 C 0.3072(3) 0.20096(18) 0.02750(17) 0.0625(6) Uani 1 1 d D . .
H3 H 0.303(2) 0.4143(15) -0.0239(14) 0.064(6) Uiso 1 1 d D . .
H4 H 0.297(3) 0.6032(19) -0.0978(17) 0.099(8) Uiso 1 1 d D . .
H5 H 0.241(3) 0.7948(19) -0.079(2) 0.125(9) Uiso 1 1 d D . .
H6 H 0.119(3) 0.8511(16) 0.063(2) 0.143(11) Uiso 1 1 d D . .
H7 H 0.066(2) 0.7201(18) 0.1944(16) 0.087(8) Uiso 1 1 d D . .
H10 H 0.1578(19) 0.2157(14) 0.1292(14) 0.065(5) Uiso 1 1 d D . .
H11A H 0.489(2) 0.2720(18) 0.2288(19) 0.096(8) Uiso 1 1 d D . .
H11B H 0.353(2) 0.2727(16) 0.2986(16) 0.088(7) Uiso 1 1 d D . .
H12A H 0.497(2) 0.097(2) 0.3315(16) 0.105(8) Uiso 1 1 d D . .
H12B H 0.309(2) 0.0744(16) 0.2628(17) 0.082(7) Uiso 1 1 d D . .
H13A H 0.475(3) -0.0233(14) 0.172(2) 0.100(8) Uiso 1 1 d D . .
H13B H 0.567(2) 0.0950(18) 0.1561(19) 0.097(8) Uiso 1 1 d D . .
H14A H 0.230(2) 0.042(2) 0.048(2) 0.128(11) Uiso 1 1 d D . .
H14B H 0.372(2) 0.0513(17) -0.0201(16) 0.090(7) Uiso 1 1 d D . .
H15A H 0.4067(19) 0.2407(14) 0.0233(15) 0.064(6) Uiso 1 1 d D . .
H15B H 0.2237(19) 0.2171(15) -0.0468(14) 0.071(6) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.636(2) . ?
O1 C1 1.359(2) . ?
O1 C2 1.382(2) . ?
C1 C8 1.445(3) . ?
C2 C3 1.328(3) . ?
C2 C10 1.489(3) . ?
C3 C9 1.429(3) . ?
C3 H3 1.014(14) . ?
C4 C5 1.369(4) . ?
C4 C9 1.405(3) . ?
C4 H4 1.036(16) . ?
C5 C6 1.384(4) . ?
C5 H5 1.042(17) . ?
C6 C7 1.373(4) . ?
C6 H6 1.024(18) . ?
C7 C8 1.411(3) . ?
C7 H7 1.013(15) . ?
C8 C9 1.404(3) . ?
C10 C15 1.518(2) . ?
C10 C11 1.527(3) . ?
C10 H10 1.041(14) . ?
C11 C12 1.516(3) . ?
C11 H11A 1.077(16) . ?
C11 H11B 1.028(15) . ?
C12 C13 1.518(3) . ?
C12 H12A 1.045(16) . ?
C12 H12B 1.065(16) . ?
C13 C14 1.518(3) . ?
C13 H13A 1.033(16) . ?
C13 H13B 1.075(16) . ?
C14 C15 1.524(3) . ?
C14 H14A 1.063(17) . ?
C14 H14B 1.045(16) . ?
C15 H15A 1.030(14) . ?
C15 H15B 1.033(15) . ?

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

O1 C1 C8 116.84(18) . . ?
O1 C1 S1 116.02(16) . . ?
O1 C2 C10 109.77(15) . . ?
C1 O1 C2 123.92(16) . . ?
C2 C3 C9 121.0(2) . . ?
C2 C10 C15 114.07(16) . . ?
C2 C10 C11 111.09(16) . . ?
C2 C10 H10 105.9(10) . . ?
C2 C3 H3 119.5(11) . . ?
C3 C2 O1 119.91(19) . . ?
C3 C2 C10 130.30(18) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C9 C3 122.2(2) . . ?
C4 C5 H5 121.2(16) . . ?
C5 C4 C9 120.0(3) . . ?
C5 C4 H4 120.9(14) . . ?
C5 C6 H6 121.3(17) . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7 124.2(13) . . ?
C6 C5 H5 117.9(16) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 117.8(17) . . ?
C7 C8 C1 120.6(2) . . ?
C8 C9 C4 119.2(2) . . ?
C8 C9 C3 118.6(2) . . ?
C8 C1 S1 127.14(17) . . ?
C8 C7 H7 116.4(13) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C3 H3 119.5(11) . . ?
C9 C4 H4 119.1(14) . . ?
C9 C8 C1 119.63(19) . . ?
C10 C11 H11A 107.4(12) . . ?
C10 C11 H11B 108.4(12) . . ?
C10 C15 H15B 109.4(10) . . ?
C10 C15 C14 110.63(18) . . ?
C10 C15 H15A 105.4(10) . . ?
C11 C12 C13 111.1(2) . . ?
C11 C10 H10 108.6(10) . . ?
C11 C12 H12A 111.7(14) . . ?
C11 C12 H12B 109.5(11) . . ?
C12 C11 C10 111.11(18) . . ?
C12 C11 H11A 110.2(13) . . ?
C12 C11 H11B 114.3(12) . . ?
C12 C13 H13A 110.5(14) . . ?
C12 C13 H13B 106.3(13) . . ?
C13 C14 C15 111.6(2) . . ?
C13 C14 H14A 110.8(16) . . ?
C13 C14 H14B 111.0(12) . . ?
C13 C12 H12A 110.5(13) . . ?
C13 C12 H12B 107.7(12) . . ?
C14 C13 C12 110.4(2) . . ?
C14 C13 H13A 110.5(14) . . ?
C14 C15 H15A 111.4(10) . . ?
C14 C13 H13B 110.1(13) . . ?
C14 C15 H15B 112.9(11) . . ?
C15 C14 H14B 105.7(12) . . ?
C15 C10 H10 106.8(10) . . ?
C15 C14 H14A 108.7(16) . . ?
C15 C10 C11 110.06(16) . . ?
H11A C11 H11B 105.0(17) . . ?
H12A C12 H12B 106.1(18) . . ?
H13A C13 H13B 108.8(19) . . ?
H14A C14 H14B 109(2) . . ?
H15A C15 H15B 106.9(15) . . ?

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

S1 C1 C8 C7 4.3(3) . . . . ?
S1 C1 C8 C9 -175.91(15) . . . . ?
O1 C1 C8 C9 3.4(3) . . . . ?
O1 C1 C8 C7 -176.33(17) . . . . ?
O1 C2 C10 C15 167.60(16) . . . . ?
O1 C2 C10 C11 -67.3(2) . . . . ?
O1 C2 C3 C9 2.2(3) . . . . ?
C1 O1 C2 C3 -0.5(3) . . . . ?
C1 O1 C2 C10 177.99(15) . . . . ?
C1 C8 C9 C4 179.01(18) . . . . ?
C1 C8 C9 C3 -2.0(3) . . . . ?
C2 C3 C9 C8 -0.9(3) . . . . ?
C2 C3 C9 C4 178.1(2) . . . . ?
C2 C10 C11 C12 175.57(18) . . . . ?
C2 O1 C1 C8 -2.3(2) . . . . ?
C2 C10 C15 C14 -177.77(18) . . . . ?
C2 O1 C1 S1 177.16(13) . . . . ?
C3 C2 C10 C15 -14.1(3) . . . . ?
C3 C2 C10 C11 111.0(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C4 C9 C8 1.5(3) . . . . ?
C5 C4 C9 C3 -177.6(2) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C6 C7 C8 C1 -179.8(2) . . . . ?
C7 C8 C9 C4 -1.2(3) . . . . ?
C7 C8 C9 C3 177.81(18) . . . . ?
C9 C4 C5 C6 -0.9(4) . . . . ?
C10 C2 C3 C9 -176.01(18) . . . . ?
C10 C11 C12 C13 57.0(3) . . . . ?
C11 C10 C15 C14 56.6(2) . . . . ?
C11 C12 C13 C14 -55.9(3) . . . . ?
C12 C13 C14 C15 55.9(3) . . . . ?
C13 C14 C15 C10 -56.8(3) . . . . ?
C15 C10 C11 C12 -57.1(2) . . . . ?

#===END

# Attachment 'TI-2.cif'

data_ti2_m
_database_code_depnum_ccdc_archive 'CCDC 656920'

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

_audit_creation_date             'Aug 07 22:13:43 2008'
_audit_creation_method           ' SHELXL-97'
_audit_update_record             
;
;

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

_chemical_name_systematic        
;
;
_chemical_name_common            3-p-tolyl-1H-isochromene-1-thione
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 O S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C16 H12 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         252.33
_chemical_compound_source        'see text'

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

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   7.4622(8)
_cell_length_b                   12.2143(12)
_cell_length_c                   14.4832(15)
_cell_angle_alpha                81.027(2)
_cell_angle_beta                 83.319(2)
_cell_angle_gamma                85.407(2)
_cell_volume                     1292.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3144
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.19
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09

_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.234
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9328
_exptl_absorpt_correction_T_max  0.9792

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

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_reflns_number            12910
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.50

_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             4778
# number of observed reflections (> n sig(I))
_reflns_number_gt                3274
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT '
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0584P)²+0.2471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4778
_refine_ls_number_parameters     421
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.045

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23940(11) 0.31934(6) 0.65293(6) 0.0716(3) Uani 1 1 d . . .
O1 O 0.2383(2) 0.14692(14) 0.57328(12) 0.0580(5) Uani 1 1 d . . .
C1 C 0.2287(3) 0.1849(2) 0.65745(19) 0.0539(7) Uani 1 1 d . . .
C2 C 0.2379(3) 0.0364(2) 0.56318(19) 0.0528(6) Uani 1 1 d . . .
C3 C 0.2250(4) -0.0401(2) 0.6395(2) 0.0620(7) Uani 1 1 d D . .
C4 C 0.1973(5) -0.0888(3) 0.8131(2) 0.0780(9) Uani 1 1 d D . .
C5 C 0.1877(5) -0.0567(3) 0.8998(2) 0.0871(10) Uani 1 1 d D . .
C6 C 0.1871(5) 0.0544(3) 0.9088(2) 0.0794(9) Uani 1 1 d D . .
C7 C 0.1972(4) 0.1335(3) 0.8306(2) 0.0679(8) Uani 1 1 d D . .
C8 C 0.2105(3) 0.1027(2) 0.74084(19) 0.0536(6) Uani 1 1 d . . .
C9 C 0.2109(4) -0.0099(2) 0.73136(19) 0.0580(7) Uani 1 1 d . . .
C10 C 0.2537(3) 0.0215(2) 0.46444(18) 0.0534(6) Uani 1 1 d . . .
C11 C 0.2582(5) 0.1105(3) 0.3932(2) 0.0768(9) Uani 1 1 d D . .
C12 C 0.2733(5) 0.0941(3) 0.3003(2) 0.0848(10) Uani 1 1 d D . .
C13 C 0.2841(4) -0.0100(3) 0.2748(2) 0.0640(7) Uani 1 1 d . . .
C14 C 0.2792(5) -0.0972(3) 0.3461(2) 0.0872(10) Uani 1 1 d D . .
C15 C 0.2631(5) -0.0825(3) 0.4392(2) 0.0860(11) Uani 1 1 d D . .
C16 C 0.2994(5) -0.0272(4) 0.1728(2) 0.0850(10) Uani 1 1 d D . .
S1' S 0.22202(9) 0.29468(7) 0.05847(5) 0.0689(3) Uani 1 1 d . . .
O1' O 0.4872(2) 0.34528(14) 0.13623(11) 0.0502(4) Uani 1 1 d . . .
C1' C 0.4280(3) 0.3346(2) 0.05299(17) 0.0476(6) Uani 1 1 d . . .
C2' C 0.6595(3) 0.37369(19) 0.14435(17) 0.0451(6) Uani 1 1 d . . .
C3' C 0.7770(3) 0.3917(2) 0.06741(18) 0.0514(6) Uani 1 1 d D . .
C4' C 0.8515(4) 0.3965(3) -0.10502(19) 0.0624(7) Uani 1 1 d D . .
C5' C 0.7973(4) 0.3889(3) -0.1907(2) 0.0681(8) Uani 1 1 d D . .
C6' C 0.6208(4) 0.3677(2) -0.1985(2) 0.0644(8) Uani 1 1 d D . .
C7' C 0.4995(4) 0.3512(2) -0.12004(19) 0.0575(7) Uani 1 1 d D . .
C8' C 0.5516(3) 0.35667(19) -0.03131(16) 0.0447(6) Uani 1 1 d . . .
C9' C 0.7281(3) 0.3819(2) -0.02329(17) 0.0475(6) Uani 1 1 d . . .
C10' C 0.6888(3) 0.37618(19) 0.24217(16) 0.0466(6) Uani 1 1 d . . .
C11' C 0.5473(4) 0.3705(2) 0.31375(18) 0.0586(7) Uani 1 1 d D . .
C12' C 0.5791(4) 0.3740(3) 0.40557(19) 0.0649(8) Uani 1 1 d D . .
C13' C 0.7494(4) 0.3835(2) 0.42919(18) 0.0575(7) Uani 1 1 d . . .
C14' C 0.8907(4) 0.3871(2) 0.3582(2) 0.0631(7) Uani 1 1 d D . .
C15' C 0.8624(4) 0.3833(2) 0.26645(19) 0.0578(7) Uani 1 1 d D . .
C16' C 0.7821(6) 0.3921(3) 0.5288(2) 0.0812(10) Uani 1 1 d D . .
H3 H 0.224(3) -0.1207(15) 0.6313(18) 0.069(8) Uiso 1 1 d D . .
H4 H 0.188(4) -0.1704(17) 0.803(2) 0.100(11) Uiso 1 1 d D . .
H5 H 0.180(4) -0.120(2) 0.9590(17) 0.101(11) Uiso 1 1 d D . .
H6 H 0.180(4) 0.080(2) 0.9744(15) 0.094(10) Uiso 1 1 d D . .
H7 H 0.195(4) 0.2160(16) 0.836(2) 0.081(9) Uiso 1 1 d D . .
H11 H 0.239(5) 0.1905(19) 0.414(3) 0.124(13) Uiso 1 1 d D . .
H12 H 0.280(5) 0.159(2) 0.2459(19) 0.110(12) Uiso 1 1 d D . .
H14 H 0.279(5) -0.1765(19) 0.329(3) 0.130(13) Uiso 1 1 d D . .
H15 H 0.254(5) -0.152(2) 0.489(2) 0.115(12) Uiso 1 1 d D . .
H16A H 0.306(7) 0.052(2) 0.130(4) 0.25(3) Uiso 1 1 d D . .
H16B H 0.194(4) -0.076(3) 0.160(3) 0.166(19) Uiso 1 1 d D . .
H16C H 0.421(4) -0.075(3) 0.156(3) 0.19(2) Uiso 1 1 d D . .
H3' H 0.903(3) 0.413(2) 0.0727(17) 0.064(8) Uiso 1 1 d D . .
H4' H 0.983(3) 0.411(2) -0.096(2) 0.083(9) Uiso 1 1 d D . .
H5' H 0.892(3) 0.395(2) -0.2482(16) 0.083(9) Uiso 1 1 d D . .
H6' H 0.575(3) 0.364(2) -0.2621(14) 0.071(8) Uiso 1 1 d D . .
H7' H 0.368(3) 0.336(2) -0.1230(19) 0.077(9) Uiso 1 1 d D . .
H11' H 0.421(3) 0.362(2) 0.2946(19) 0.077(9) Uiso 1 1 d D . .
H12' H 0.468(3) 0.368(2) 0.4561(16) 0.075(8) Uiso 1 1 d D . .
H14' H 1.019(3) 0.393(2) 0.377(2) 0.083(9) Uiso 1 1 d D . .
H15' H 0.970(3) 0.388(2) 0.2150(16) 0.075(8) Uiso 1 1 d D . .
H16D H 0.806(5) 0.4765(16) 0.533(3) 0.132(14) Uiso 1 1 d D . .
H16E H 0.891(4) 0.338(2) 0.553(3) 0.141(15) Uiso 1 1 d D . .
H16F H 0.660(3) 0.376(3) 0.574(2) 0.119(13) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.641(3) . ?
O1 C1 1.363(3) . ?
O1 C2 1.380(3) . ?
C1 C8 1.446(4) . ?
C2 C3 1.332(4) . ?
C2 C10 1.460(4) . ?
C3 C9 1.425(4) . ?
C3 H3 1.010(17) . ?
C4 C5 1.366(4) . ?
C4 C9 1.404(4) . ?
C4 H4 1.039(18) . ?
C5 C6 1.383(5) . ?
C5 H5 1.061(18) . ?
C6 C7 1.368(4) . ?
C6 H6 1.041(18) . ?
C7 C8 1.400(4) . ?
C7 H7 1.023(17) . ?
C8 C9 1.403(4) . ?
C10 C15 1.370(4) . ?
C10 C11 1.376(4) . ?
C11 C12 1.381(4) . ?
C11 H11 1.061(19) . ?
C12 C13 1.373(4) . ?
C12 H12 1.029(18) . ?
C13 C14 1.363(4) . ?
C13 C16 1.514(4) . ?
C14 C15 1.378(4) . ?
C14 H14 1.038(19) . ?
C15 H15 1.026(18) . ?
C16 H16A 1.063(21) . ?
C16 H16B 1.067(18) . ?
C16 H16C 1.060(19) . ?
S1' C1' 1.639(2) . ?
O1' C1' 1.359(3) . ?
O1' C2' 1.381(3) . ?
C1' C8' 1.446(3) . ?
C2' C3' 1.336(3) . ?
C2' C10' 1.464(3) . ?
C3' C9' 1.428(3) . ?
C3' H3' 1.008(16) . ?
C4' C5' 1.368(4) . ?
C4' C9' 1.410(3) . ?
C4' H4' 1.041(17) . ?
C5' C6' 1.383(4) . ?
C5' H5' 1.023(17) . ?
C6' C7' 1.368(4) . ?
C6' H6' 1.028(17) . ?
C7' C8' 1.398(3) . ?
C7' H7' 1.021(17) . ?
C8' C9' 1.398(3) . ?
C10' C11' 1.389(3) . ?
C10' C15' 1.394(3) . ?
C11' C12' 1.385(4) . ?
C11' H11' 1.035(17) . ?
C12' C13' 1.372(4) . ?
C12' H12' 1.039(17) . ?
C13' C14' 1.383(4) . ?
C13' C16' 1.511(4) . ?
C14' C15' 1.378(4) . ?
C14' H14' 1.039(17) . ?
C15' H15' 1.029(17) . ?
C16' H16D 1.073(18) . ?
C16' H16E 1.063(18) . ?
C16' H16F 1.067(17) . ?

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

O1 C1 C8 116.7(2) . . ?
O1 C1 S1 116.25(19) . . ?
O1 C2 C10 111.7(2) . . ?
C1 O1 C2 124.4(2) . . ?
C2 C3 C9 121.1(3) . . ?
C2 C3 H3 118.6(15) . . ?
C3 C2 O1 119.4(2) . . ?
C3 C2 C10 128.9(2) . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 117.3(18) . . ?
C4 C9 C3 122.4(3) . . ?
C5 C4 C9 120.6(3) . . ?
C5 C4 H4 123.6(18) . . ?
C5 C6 H6 121.5(17) . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 120.9(16) . . ?
C6 C5 H5 122.1(18) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 118.3(18) . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 C1 121.0(3) . . ?
C8 C9 C3 119.0(2) . . ?
C8 C1 S1 127.1(2) . . ?
C8 C9 C4 118.6(3) . . ?
C8 C7 H7 118.7(16) . . ?
C9 C8 C1 119.4(2) . . ?
C9 C4 H4 115.7(18) . . ?
C9 C3 H3 120.2(15) . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 116(2) . . ?
C10 C15 C14 121.1(3) . . ?
C10 C15 H15 121(2) . . ?
C11 C10 C2 121.8(2) . . ?
C11 C12 H12 122(2) . . ?
C12 C11 H11 123(2) . . ?
C12 C13 C16 121.8(3) . . ?
C13 C14 C15 122.2(3) . . ?
C13 C14 H14 118(2) . . ?
C13 C12 C11 122.1(3) . . ?
C13 C12 H12 116(2) . . ?
C13 C16 H16A 108(3) . . ?
C13 C16 H16B 111(2) . . ?
C13 C16 H16C 110(3) . . ?
C14 C13 C12 116.4(3) . . ?
C14 C13 C16 121.7(3) . . ?
C14 C15 H15 118(2) . . ?
C15 C10 C11 117.4(3) . . ?
C15 C10 C2 120.9(2) . . ?
C15 C14 H14 120(2) . . ?
H16A C16 H16B 115(3) . . ?
H16A C16 H16C 108(3) . . ?
H16B C16 H16C 105(3) . . ?
O1' C1' C8' 117.8(2) . . ?
O1' C1' S1' 116.14(18) . . ?
O1' C2' C10' 112.07(19) . . ?
C1' O1' C2' 123.44(18) . . ?
C2' C3' C9' 121.3(2) . . ?
C2' C3' H3' 120.0(15) . . ?
C3' C2' O1' 119.5(2) . . ?
C3' C2' C10' 128.4(2) . . ?
C4' C5' C6' 120.6(3) . . ?
C4' C9' C3' 122.4(2) . . ?
C4' C5' H5' 118.6(16) . . ?
C5' C4' C9' 120.3(3) . . ?
C5' C4' H4' 123.0(16) . . ?
C5' C6' H6' 122.4(15) . . ?
C6' C7' C8' 120.5(3) . . ?
C6' C7' H7' 122.5(16) . . ?
C6' C5' H5' 120.7(16) . . ?
C7' C6' C5' 120.2(3) . . ?
C7' C6' H6' 117.4(15) . . ?
C7' C8' C1' 121.4(2) . . ?
C8' C9' C4' 118.8(2) . . ?
C8' C9' C3' 118.8(2) . . ?
C8' C1' S1' 126.01(18) . . ?
C8' C7' H7' 117.0(16) . . ?
C9' C8' C7' 119.6(2) . . ?
C9' C8' C1' 119.0(2) . . ?
C9' C3' H3' 118.7(15) . . ?
C9' C4' H4' 116.7(16) . . ?
C10' C11' H11' 116.4(16) . . ?
C10' C15' H15' 119.6(15) . . ?
C13' C16' H16D 109(2) . . ?
C13' C16' H16E 113(2) . . ?
C11' C10' C15' 117.7(2) . . ?
C11' C10' C2' 121.9(2) . . ?
C11' C12' H12' 116.9(15) . . ?
C12' C13' C14' 117.7(2) . . ?
C12' C13' C16' 121.5(3) . . ?
C12' C11' C10' 120.5(3) . . ?
C12' C11' H11' 123.1(16) . . ?
C13' C12' C11' 121.7(3) . . ?
C13' C12' H12' 121.4(15) . . ?
C13' C14' H14' 116.9(16) . . ?
C13' C16' H16F 109(2) . . ?
C14' C15' C10' 120.7(3) . . ?
C14' C15' H15' 119.6(15) . . ?
C14' C13' C16' 120.8(3) . . ?
C15' C14' C13' 121.6(3) . . ?
C15' C14' H14' 121.5(16) . . ?
C15' C10' C2' 120.4(2) . . ?
H16D C16' H16E 110(2) . . ?
H16D C16' H16F 105(2) . . ?
H16E C16' H16F 110(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

S1 C1 C8 C7 1.0(4) . . . . ?
S1 C1 C8 C9 -177.4(2) . . . . ?
O1 C1 C8 C9 2.4(3) . . . . ?
O1 C2 C3 C9 0.3(4) . . . . ?
O1 C1 C8 C7 -179.2(2) . . . . ?
O1 C2 C10 C15 177.4(3) . . . . ?
O1 C2 C10 C11 -3.2(4) . . . . ?
C1 O1 C2 C3 0.9(4) . . . . ?
C1 C8 C9 C3 -1.4(4) . . . . ?
C1 C8 C9 C4 178.5(3) . . . . ?
C1 O1 C2 C10 -178.7(2) . . . . ?
C2 O1 C1 C8 -2.2(3) . . . . ?
C2 O1 C1 S1 177.64(18) . . . . ?
C2 C10 C11 C12 180.0(3) . . . . ?
C2 C3 C9 C8 0.0(4) . . . . ?
C2 C3 C9 C4 -179.9(3) . . . . ?
C2 C10 C15 C14 -179.6(3) . . . . ?
C3 C2 C10 C15 -2.2(5) . . . . ?
C3 C2 C10 C11 177.2(3) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C5 C4 C9 C8 -1.3(5) . . . . ?
C5 C4 C9 C3 178.7(3) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C6 C7 C8 C1 -177.4(3) . . . . ?
C7 C8 C9 C4 0.1(4) . . . . ?
C7 C8 C9 C3 -179.8(3) . . . . ?
C9 C4 C5 C6 1.4(6) . . . . ?
C10 C2 C3 C9 179.9(2) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C11 C12 C13 C16 179.6(3) . . . . ?
C11 C10 C15 C14 0.9(5) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C10 -0.9(6) . . . . ?
C15 C10 C11 C12 -0.6(5) . . . . ?
C16 C13 C14 C15 -179.2(3) . . . . ?
S1' C1' C8' C7' 3.6(4) . . . . ?
S1' C1' C8' C9' -175.12(19) . . . . ?
O1' C1' C8' C7' -177.9(2) . . . . ?
O1' C1' C8' C9' 3.4(3) . . . . ?
O1' C2' C3' C9' -0.2(4) . . . . ?
O1' C2' C10' C11' -10.9(3) . . . . ?
O1' C2' C10' C15' 168.4(2) . . . . ?
C1' O1' C2' C3' -0.2(3) . . . . ?
C1' O1' C2' C10' -178.3(2) . . . . ?
C1' C8' C9' C4' 176.0(2) . . . . ?
C1' C8' C9' C3' -3.8(3) . . . . ?
C2' O1' C1' C8' -1.4(3) . . . . ?
C2' O1' C1' S1' 177.26(17) . . . . ?
C2' C3' C9' C8' 2.3(4) . . . . ?
C2' C3' C9' C4' -177.6(3) . . . . ?
C2' C10' C15' C14' 179.2(2) . . . . ?
C2' C10' C11' C12' -179.4(2) . . . . ?
C3' C2' C10' C11' 171.1(3) . . . . ?
C3' C2' C10' C15' -9.5(4) . . . . ?
C4' C5' C6' C7' -1.7(5) . . . . ?
C5' C6' C7' C8' 0.7(4) . . . . ?
C5' C4' C9' C8' 1.8(4) . . . . ?
C5' C4' C9' C3' -178.4(3) . . . . ?
C6' C7' C8' C9' 1.5(4) . . . . ?
C6' C7' C8' C1' -177.2(2) . . . . ?
C7' C8' C9' C4' -2.7(4) . . . . ?
C7' C8' C9' C3' 177.4(2) . . . . ?
C9' C4' C5' C6' 0.4(5) . . . . ?
C10' C2' C3' C9' 177.6(2) . . . . ?
C10' C11' C12' C13' 0.2(4) . . . . ?
C11' C12' C13' C14' -1.3(4) . . . . ?
C11' C12' C13' C16' 177.4(3) . . . . ?
C11' C10' C15' C14' -1.5(4) . . . . ?
C12' C13' C14' C15' 1.1(4) . . . . ?
C13' C14' C15' C10' 0.4(4) . . . . ?
C15' C10' C11' C12' 1.2(4) . . . . ?
C16' C13' C14' C15' -177.7(3) . . . . ?

#===END

# Attachment 'TI-3.cif'

data_vh3n_m
_database_code_depnum_ccdc_archive 'CCDC 656922'
#==============================================================================

_audit_creation_date             'Aug 07 17:24:12 2008'
_audit_creation_method           ' SHELXL-97'
_audit_update_record             
;
;

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

_chemical_name_systematic        
;
;
_chemical_name_common            3-(4-methoxyphenyl)-1H-isochromene-1-thione
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C16 H12 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         268.33
_chemical_compound_source        'see text'

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

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   7.5948(14)
_cell_length_b                   10.988(2)
_cell_length_c                   15.526(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.149(3)
_cell_angle_gamma                90
_cell_volume                     1288.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    928
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.71
_cell_special_details            
;
;

_exptl_crystal_description       block
_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08

_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.245
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9025
_exptl_absorpt_correction_T_max  0.9807

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

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_reflns_number            9306
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.50

_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2389
# number of observed reflections (> n sig(I))
_reflns_number_gt                1850
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_cell_refinement       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT V6.45a, (Bruker, 2004)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0547P)²+0.1537P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2389
_refine_ls_number_parameters     220
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.035

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.08808(9) 0.34050(4) 1.02103(3) 0.0712(2) Uani 1 1 d . . .
O1 O 0.20393(16) 0.13455(10) 0.97464(7) 0.0461(3) Uani 1 1 d . . .
O2 O 0.4545(2) -0.17482(13) 0.66789(10) 0.0708(4) Uani 1 1 d . . .
C1 C 0.1455(2) 0.19794(16) 1.04142(11) 0.0452(4) Uani 1 1 d . . .
C2 C 0.2499(2) 0.01247(14) 0.97930(10) 0.0413(4) Uani 1 1 d . . .
C3 C 0.2391(2) -0.04893(16) 1.05298(12) 0.0463(4) Uani 1 1 d D . .
C4 C 0.1790(3) -0.05020(19) 1.20708(12) 0.0554(5) Uani 1 1 d D . .
C5 C 0.1307(3) 0.0107(2) 1.27784(13) 0.0601(5) Uani 1 1 d D . .
C6 C 0.0870(3) 0.1336(2) 1.27272(12) 0.0576(5) Uani 1 1 d D . .
C7 C 0.0895(3) 0.19460(18) 1.19576(11) 0.0507(5) Uani 1 1 d D . .
C8 C 0.1397(2) 0.13460(15) 1.12248(10) 0.0418(4) Uani 1 1 d . . .
C9 C 0.1856(2) 0.01050(15) 1.12811(10) 0.0439(4) Uani 1 1 d . . .
C10 C 0.3049(2) -0.03198(15) 0.89747(11) 0.0425(4) Uani 1 1 d . . .
C11 C 0.2971(2) 0.04057(16) 0.82431(11) 0.0473(4) Uani 1 1 d D . .
C12 C 0.3448(2) -0.00321(17) 0.74612(12) 0.0517(5) Uani 1 1 d D . .
C13 C 0.4048(2) -0.12151(17) 0.74119(13) 0.0518(5) Uani 1 1 d . . .
C14 C 0.4171(3) -0.19468(18) 0.81400(14) 0.0569(5) Uani 1 1 d D . .
C15 C 0.3668(2) -0.15162(16) 0.89075(13) 0.0517(5) Uani 1 1 d D . .
C16 C 0.4555(4) -0.1014(3) 0.59251(16) 0.0819(7) Uani 1 1 d D . .
H3 H 0.274(3) -0.1368(14) 1.0559(12) 0.061(5) Uiso 1 1 d D . .
H4 H 0.213(2) -0.1389(14) 1.2081(12) 0.059(5) Uiso 1 1 d D . .
H5 H 0.125(3) -0.0325(17) 1.3333(10) 0.067(6) Uiso 1 1 d D . .
H6 H 0.052(3) 0.1808(17) 1.3232(12) 0.074(6) Uiso 1 1 d D . .
H7 H 0.051(2) 0.2823(15) 1.1888(13) 0.068(6) Uiso 1 1 d D . .
H11 H 0.253(2) 0.1292(14) 0.8270(12) 0.061(5) Uiso 1 1 d D . .
H12 H 0.330(2) 0.0534(17) 0.6949(11) 0.067(6) Uiso 1 1 d D . .
H14 H 0.462(2) -0.2803(15) 0.8101(13) 0.072(6) Uiso 1 1 d D . .
H15 H 0.377(3) -0.2066(18) 0.9424(12) 0.074(6) Uiso 1 1 d D . .
H16A H 0.516(4) -0.155(2) 0.5490(16) 0.131(11) Uiso 1 1 d D . .
H16B H 0.325(2) -0.085(2) 0.5654(14) 0.089(8) Uiso 1 1 d D . .
H16C H 0.529(3) -0.0211(19) 0.6040(17) 0.112(9) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.6477(18) . ?
O1 C1 1.3621(19) . ?
O1 C2 1.3860(18) . ?
O2 C13 1.368(2) . ?
O2 C16 1.422(3) . ?
C1 C8 1.443(2) . ?
C2 C3 1.338(2) . ?
C2 C10 1.463(2) . ?
C3 C9 1.433(2) . ?
C3 H3 1.002(14) . ?
C4 C5 1.370(3) . ?
C4 C9 1.401(2) . ?
C4 H4 1.008(14) . ?
C5 C6 1.390(3) . ?
C5 H5 0.987(15) . ?
C6 C7 1.372(3) . ?
C6 H6 0.998(15) . ?
C7 C8 1.403(2) . ?
C7 H7 1.010(15) . ?
C8 C9 1.408(2) . ?
C10 C11 1.384(2) . ?
C10 C15 1.404(2) . ?
C11 C12 1.390(2) . ?
C11 H11 1.033(14) . ?
C12 C13 1.382(3) . ?
C12 H12 1.007(15) . ?
C13 C14 1.382(3) . ?
C14 C15 1.374(3) . ?
C14 H14 1.006(15) . ?
C15 H15 1.001(15) . ?
C16 H16A 1.040(18) . ?
C16 H16B 1.049(16) . ?
C16 H16C 1.051(17) . ?

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

O1 C1 C8 117.40(15) . . ?
O1 C1 S1 116.17(12) . . ?
O1 C2 C10 111.81(14) . . ?
O2 C13 C14 115.52(17) . . ?
O2 C16 H16A 104.6(16) . . ?
O2 C16 H16C 112.7(15) . . ?
O2 C16 H16B 109.7(13) . . ?
O2 C13 C12 124.79(19) . . ?
C1 O1 C2 123.77(13) . . ?
C2 C3 C9 120.98(16) . . ?
C2 C3 H3 118.9(11) . . ?
C3 C2 O1 119.63(15) . . ?
C3 C2 C10 128.56(16) . . ?
C4 C5 C6 120.77(18) . . ?
C4 C9 C8 118.91(16) . . ?
C4 C9 C3 122.36(17) . . ?
C4 C5 H5 120.2(12) . . ?
C5 C4 C9 120.46(19) . . ?
C5 C4 H4 123.4(11) . . ?
C5 C6 H6 122.8(12) . . ?
C6 C7 C8 120.46(19) . . ?
C6 C7 H7 121.9(11) . . ?
C6 C5 H5 119.0(12) . . ?
C7 C6 C5 119.92(19) . . ?
C7 C6 H6 117.3(12) . . ?
C7 C8 C9 119.47(15) . . ?
C7 C8 C1 121.14(16) . . ?
C8 C1 S1 126.44(13) . . ?
C8 C9 C3 118.73(15) . . ?
C8 C7 H7 117.6(11) . . ?
C9 C3 H3 120.1(11) . . ?
C9 C4 H4 116.2(11) . . ?
C9 C8 C1 119.39(15) . . ?
C10 C11 C12 121.69(17) . . ?
C10 C11 H11 119.7(10) . . ?
C10 C15 H15 120.2(12) . . ?
C11 C10 C15 117.63(16) . . ?
C11 C10 C2 121.95(15) . . ?
C11 C12 H12 117.4(11) . . ?
C12 C11 H11 118.6(11) . . ?
C13 C12 C11 119.50(18) . . ?
C13 O2 C16 117.88(17) . . ?
C13 C12 H12 123.1(11) . . ?
C13 C14 H14 119.2(11) . . ?
C14 C15 C10 120.89(18) . . ?
C14 C15 H15 118.9(12) . . ?
C14 C13 C12 119.69(17) . . ?
C15 C14 C13 120.56(17) . . ?
C15 C14 H14 120.2(12) . . ?
C15 C10 C2 120.41(16) . . ?
H16A C16 H16B 107(2) . . ?
H16A C16 H16C 109(2) . . ?
H16B C16 H16C 113(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

S1 C1 C8 C7 -3.2(3) . . . . ?
S1 C1 C8 C9 176.97(14) . . . . ?
O1 C1 C8 C9 -3.0(2) . . . . ?
O1 C2 C3 C9 -1.8(2) . . . . ?
O1 C2 C10 C11 -4.4(2) . . . . ?
O1 C1 C8 C7 176.88(15) . . . . ?
O1 C2 C10 C15 176.12(15) . . . . ?
O2 C13 C14 C15 -178.47(17) . . . . ?
C1 O1 C2 C3 -0.6(2) . . . . ?
C1 C8 C9 C4 -179.82(16) . . . . ?
C1 O1 C2 C10 179.00(14) . . . . ?
C1 C8 C9 C3 0.8(2) . . . . ?
C2 C3 C9 C4 -177.71(16) . . . . ?
C2 C3 C9 C8 1.7(2) . . . . ?
C2 O1 C1 C8 3.0(2) . . . . ?
C2 O1 C1 S1 -176.96(12) . . . . ?
C2 C10 C11 C12 -178.16(15) . . . . ?
C2 C10 C15 C14 179.33(16) . . . . ?
C3 C2 C10 C11 175.19(17) . . . . ?
C3 C2 C10 C15 -4.3(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C5 C4 C9 C3 178.61(17) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C1 -179.08(17) . . . . ?
C7 C8 C9 C4 0.3(2) . . . . ?
C7 C8 C9 C3 -179.09(16) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C10 C2 C3 C9 178.64(15) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 O2 179.60(16) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C15 C10 C11 C12 1.4(3) . . . . ?
C16 O2 C13 C14 -176.01(19) . . . . ?
C16 O2 C13 C12 4.2(3) . . . . ?

#===END

# Attachment 'TI-4.cif'

data_vh6_m
_database_code_depnum_ccdc_archive 'CCDC 656924'
#==============================================================================

_audit_creation_date             'Aug 07 23:30:28 2008'
_audit_creation_method           ' SHELXL-97'
_audit_update_record             
;
;

_chemical_name_systematic        
;
;
_chemical_name_common            '3-(2- Furyl)-1H-isochromene-1-thione'
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 O2 S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C13 H8 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         228.26
_chemical_compound_source        'see text'

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

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   4.0478(6)
_cell_length_b                   13.5257(19)
_cell_length_c                   19.180(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1050.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2624
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.05
_cell_special_details            
;
;

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06

_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.286
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9141
_exptl_absorpt_correction_T_max  0.9830

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

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_reflns_number            7813
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.50

_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             1945
# number of observed reflections (> n sig(I))
_reflns_number_gt                1710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_cell_refinement       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT V6.45a, (Bruker, 2004)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0322P)²+0.0944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack(1983), 758 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_number_reflns         1945
_refine_ls_number_parameters     177
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0702
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.029

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87860(18) -0.07987(4) 0.15159(3) 0.0610(2) Uani 1 1 d . . .
O1 O 0.9201(4) 0.02890(10) 0.26012(7) 0.0486(4) Uani 1 1 d . . .
O2 O 0.9957(5) 0.16943(11) 0.41637(7) 0.0638(5) Uani 1 1 d . . .
C1 C 0.8077(5) 0.02349(14) 0.19267(10) 0.0433(5) Uani 1 1 d . . .
C2 C 0.8757(6) 0.11190(14) 0.30117(10) 0.0432(5) Uani 1 1 d . . .
C3 C 0.7163(6) 0.19112(15) 0.27829(11) 0.0462(6) Uani 1 1 d D . .
C4 C 0.4219(6) 0.27534(15) 0.18090(12) 0.0521(6) Uani 1 1 d D . .
C5 C 0.3109(7) 0.27494(18) 0.11352(13) 0.0568(6) Uani 1 1 d D . .
C6 C 0.3606(6) 0.19196(17) 0.07139(12) 0.0538(6) Uani 1 1 d D . .
C7 C 0.5197(6) 0.11057(16) 0.09707(11) 0.0485(5) Uani 1 1 d D . .
C8 C 0.6372(5) 0.11000(14) 0.16583(10) 0.0407(5) Uani 1 1 d . . .
C9 C 0.5892(6) 0.19315(14) 0.20844(10) 0.0423(5) Uani 1 1 d . . .
C10 C 1.0296(6) 0.09532(16) 0.36820(10) 0.0470(5) Uani 1 1 d . . .
C11 C 1.2098(6) 0.02103(18) 0.39443(12) 0.0553(6) Uani 1 1 d D . .
C12 C 1.2970(7) 0.0489(2) 0.46331(13) 0.0672(7) Uani 1 1 d D . .
C13 C 1.1652(8) 0.1365(2) 0.47440(12) 0.0726(8) Uani 1 1 d D . .
H3 H 0.685(6) 0.2519(12) 0.3070(10) 0.058(6) Uiso 1 1 d D . .
H4 H 0.397(7) 0.3362(13) 0.2113(10) 0.078(8) Uiso 1 1 d D . .
H5 H 0.176(5) 0.3327(14) 0.0950(11) 0.072(7) Uiso 1 1 d D . .
H6 H 0.280(6) 0.1937(16) 0.0222(8) 0.065(7) Uiso 1 1 d D . .
H7 H 0.550(6) 0.0494(12) 0.0685(9) 0.057(6) Uiso 1 1 d D . .
H11 H 1.273(6) -0.0409(14) 0.3705(11) 0.074(8) Uiso 1 1 d D . .
H12 H 1.441(6) 0.0105(15) 0.4981(10) 0.065(7) Uiso 1 1 d D . .
H13 H 1.151(7) 0.1873(15) 0.5141(10) 0.083(8) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.630(2) . ?
O1 C1 1.373(2) . ?
O1 C2 1.383(2) . ?
O2 C10 1.370(2) . ?
O2 C13 1.381(3) . ?
C1 C8 1.453(3) . ?
C2 C3 1.326(3) . ?
C2 C10 1.446(3) . ?
C3 C9 1.435(3) . ?
C3 H3 0.997(15) . ?
C4 C5 1.368(3) . ?
C4 C9 1.405(3) . ?
C4 H4 1.014(16) . ?
C5 C6 1.397(3) . ?
C5 H5 1.018(16) . ?
C6 C7 1.367(3) . ?
C6 H6 1.000(15) . ?
C7 C8 1.402(3) . ?
C7 H7 0.999(15) . ?
C8 C9 1.404(3) . ?
C10 C11 1.340(3) . ?
C11 C12 1.418(3) . ?
C11 H11 0.989(16) . ?
C12 C13 1.317(4) . ?
C12 H12 1.026(16) . ?
C13 H13 1.028(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag

O1 C1 C8 116.63(17) . . ?
O1 C1 S1 116.27(15) . . ?
O1 C2 C10 108.93(17) . . ?
O2 C10 C2 116.29(19) . . ?
O2 C13 H13 110.8(14) . . ?
C1 O1 C2 122.45(15) . . ?
C2 C3 C9 119.93(19) . . ?
C2 C3 H3 123.0(12) . . ?
C3 C2 O1 122.07(18) . . ?
C3 C2 C10 129.00(19) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.2(13) . . ?
C4 C9 C3 122.61(19) . . ?
C5 C4 C9 120.7(2) . . ?
C5 C4 H4 121.0(13) . . ?
C5 C6 H6 118.7(13) . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 121.8(12) . . ?
C6 C5 H5 119.5(13) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 120.9(13) . . ?
C7 C8 C9 119.75(19) . . ?
C7 C8 C1 119.93(18) . . ?
C8 C1 S1 127.10(15) . . ?
C8 C7 H7 117.9(12) . . ?
C8 C9 C4 118.80(19) . . ?
C8 C9 C3 118.59(18) . . ?
C9 C4 H4 118.2(13) . . ?
C9 C3 H3 117.0(12) . . ?
C9 C8 C1 120.32(18) . . ?
C10 O2 C13 104.95(19) . . ?
C10 C11 C12 106.6(2) . . ?
C10 C11 H11 127.1(14) . . ?
C11 C10 O2 110.49(19) . . ?
C11 C10 C2 133.2(2) . . ?
C11 C12 H12 127.8(13) . . ?
C12 C13 O2 111.2(2) . . ?
C12 C13 H13 138.1(14) . . ?
C12 C11 H11 126.3(14) . . ?
C13 C12 C11 106.8(3) . . ?
C13 C12 H12 125.4(12) . . ?

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

S1 C1 C8 C9 178.63(16) . . . . ?
S1 C1 C8 C7 -1.4(3) . . . . ?
O1 C2 C3 C9 -1.2(3) . . . . ?
O1 C1 C8 C7 179.04(19) . . . . ?
O1 C1 C8 C9 -1.0(3) . . . . ?
O1 C2 C10 C11 3.9(3) . . . . ?
O1 C2 C10 O2 -177.34(17) . . . . ?
O2 C10 C11 C12 0.0(3) . . . . ?
C1 C8 C9 C4 -179.7(2) . . . . ?
C1 C8 C9 C3 0.9(3) . . . . ?
C1 O1 C2 C3 1.2(3) . . . . ?
C1 O1 C2 C10 -178.36(18) . . . . ?
C2 O1 C1 C8 -0.1(3) . . . . ?
C2 C10 C11 C12 178.8(2) . . . . ?
C2 O1 C1 S1 -179.69(15) . . . . ?
C2 C3 C9 C8 0.2(3) . . . . ?
C2 C3 C9 C4 -179.2(2) . . . . ?
C3 C2 C10 C11 -175.6(3) . . . . ?
C3 C2 C10 O2 3.2(3) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C5 C4 C9 C3 178.6(2) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 C1 -179.6(2) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C7 C8 C9 C3 -179.1(2) . . . . ?
C9 C4 C5 C6 0.6(4) . . . . ?
C10 C2 C3 C9 178.2(2) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C10 O2 C13 C12 0.4(3) . . . . ?
C11 C12 C13 O2 -0.4(3) . . . . ?
C13 O2 C10 C11 -0.2(3) . . . . ?
C13 O2 C10 C2 -179.3(2) . . . . ?

#===END

# Attachment 'TI-5.cif'

data_vh4_m
_database_code_depnum_ccdc_archive 'CCDC 658572'
#==============================================================================

_audit_creation_date             'Aug 07 22:53:33 2008'
_audit_creation_method           ' SHELXL-97'
_audit_update_record             
;
;

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 O S'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H10 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         238.30
_chemical_compound_source        'see text'

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

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   3.8992(5)
_cell_length_b                   15.2947(18)
_cell_length_c                   19.007(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.701(2)
_cell_angle_gamma                90
_cell_volume                     1132.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    958
_cell_measurement_theta_min      1.73
_cell_measurement_theta_max      24.18
_cell_special_details            
;
;

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03

_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.263
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.9426
_exptl_absorpt_correction_T_max  0.9922

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

_exptl_special_details           
;
;
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0

loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
_diffrn_reflns_number            7940
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;
# number of unique reflections
_reflns_number_total             1998
# number of observed reflections (> n sig(I))
_reflns_number_gt                1301
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_cell_refinement       'Bruker SMART V5.628, (Bruker, 2004)'
_computing_data_reduction        'Bruker SAINT V6.45a, (Bruker, 2004)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 1990)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1998
_refine_ls_number_parameters     194
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.053

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0978(3) -0.14695(7) 0.79040(6) 0.0592(4) Uani 1 1 d . . .
O1 O 0.1255(6) 0.01126(15) 0.83289(12) 0.0436(7) Uani 1 1 d . . .
C1 C 0.0167(9) -0.0430(2) 0.77922(18) 0.0394(9) Uani 1 1 d . . .
C2 C 0.0867(9) 0.1014(2) 0.83110(18) 0.0363(9) Uani 1 1 d . . .
C3 C -0.0619(9) 0.1400(2) 0.77465(18) 0.0396(9) Uani 1 1 d D . .
C4 C -0.3482(10) 0.1281(3) 0.6559(2) 0.0480(11) Uani 1 1 d D . .
C5 C -0.4711(10) 0.0772(3) 0.6006(2) 0.0520(11) Uani 1 1 d D . .
C6 C -0.4406(10) -0.0129(3) 0.6038(2) 0.0532(11) Uani 1 1 d D . .
C7 C -0.2841(10) -0.0528(3) 0.6618(2) 0.0485(11) Uani 1 1 d D . .
C8 C -0.1531(9) -0.0016(2) 0.71811(18) 0.0375(9) Uani 1 1 d . . .
C9 C -0.1894(9) 0.0892(2) 0.71545(18) 0.0360(9) Uani 1 1 d . . .
C10 C 0.2211(8) 0.1419(2) 0.89684(18) 0.0372(9) Uani 1 1 d . . .
C11 C 0.2591(11) 0.0939(3) 0.9587(2) 0.0499(11) Uani 1 1 d D . .
C12 C 0.3819(11) 0.1329(3) 1.0208(2) 0.0581(12) Uani 1 1 d D . .
C13 C 0.4731(11) 0.2192(3) 1.0209(2) 0.0556(12) Uani 1 1 d D . .
C14 C 0.4381(10) 0.2676(3) 0.9600(2) 0.0558(11) Uani 1 1 d D . .
C15 C 0.3127(10) 0.2295(3) 0.8980(2) 0.0476(10) Uani 1 1 d D . .
H3 H -0.100(8) 0.2074(13) 0.7718(18) 0.049(10) Uiso 1 1 d D . .
H4 H -0.370(9) 0.1964(13) 0.652(2) 0.061(12) Uiso 1 1 d D . .
H5 H -0.595(9) 0.105(2) 0.5559(15) 0.081(14) Uiso 1 1 d D . .
H6 H -0.535(9) -0.054(2) 0.5645(15) 0.058(11) Uiso 1 1 d D . .
H7 H -0.271(9) -0.1197(13) 0.6647(19) 0.054(11) Uiso 1 1 d D . .
H11 H 0.196(9) 0.0274(14) 0.956(2) 0.071(13) Uiso 1 1 d D . .
H12 H 0.417(10) 0.089(2) 1.0631(17) 0.087(15) Uiso 1 1 d D . .
H13 H 0.582(8) 0.249(2) 1.0655(14) 0.067(12) Uiso 1 1 d D . .
H14 H 0.513(8) 0.3330(14) 0.9608(19) 0.060(11) Uiso 1 1 d D . .
H15 H 0.309(8) 0.266(2) 0.8509(13) 0.057(11) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.633(4) . ?
O1 C1 1.367(4) . ?
O1 C2 1.387(4) . ?
C1 C8 1.455(5) . ?
C2 C3 1.333(5) . ?
C2 C10 1.469(5) . ?
C3 C9 1.437(5) . ?
C3 H3 1.043(18) . ?
C4 C5 1.376(5) . ?
C4 C9 1.397(5) . ?
C4 H4 1.050(18) . ?
C5 C6 1.383(6) . ?
C5 H5 1.049(19) . ?
C6 C7 1.377(5) . ?
C6 H6 1.034(18) . ?
C7 C8 1.403(5) . ?
C7 H7 1.026(18) . ?
C8 C9 1.397(5) . ?
C10 C15 1.387(5) . ?
C10 C11 1.388(5) . ?
C11 C12 1.388(5) . ?
C11 H11 1.047(19) . ?
C12 C13 1.367(6) . ?
C12 H12 1.051(19) . ?
C13 C14 1.376(6) . ?
C13 H13 1.039(19) . ?
C14 C15 1.383(5) . ?
C14 H14 1.042(19) . ?
C15 H15 1.051(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag

O1 C1 C8 116.4(3) . . ?
O1 C2 C10 111.4(3) . . ?
O1 C1 S1 116.3(2) . . ?
C1 O1 C2 123.7(3) . . ?
C2 C3 C9 120.8(3) . . ?
C2 C3 H3 122.4(19) . . ?
C3 C2 O1 120.2(3) . . ?
C3 C2 C10 128.4(3) . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 121(2) . . ?
C4 C9 C8 119.5(3) . . ?
C4 C9 C3 121.9(3) . . ?
C5 C4 C9 120.2(4) . . ?
C5 C4 H4 119(2) . . ?
C5 C6 H6 124(2) . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7 120(2) . . ?
C6 C5 H5 118(2) . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6 116(2) . . ?
C7 C8 C1 120.2(3) . . ?
C8 C1 S1 127.3(3) . . ?
C8 C9 C3 118.6(3) . . ?
C8 C7 H7 120(2) . . ?
C9 C3 H3 116.8(19) . . ?
C9 C4 H4 121(2) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 C1 120.2(3) . . ?
C10 C11 C12 120.7(4) . . ?
C10 C15 H15 120(2) . . ?
C10 C11 H11 117(2) . . ?
C11 C10 C2 121.1(3) . . ?
C11 C12 H12 114(2) . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13 122(2) . . ?
C12 C11 H11 122(2) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14 119(2) . . ?
C13 C12 H12 126(2) . . ?
C14 C13 H13 118(2) . . ?
C14 C15 C10 120.0(4) . . ?
C14 C15 H15 120(2) . . ?
C15 C14 H14 120(2) . . ?
C15 C10 C11 118.8(3) . . ?
C15 C10 C2 120.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

S1 C1 C8 C9 -177.1(3) . . . . ?
S1 C1 C8 C7 3.5(5) . . . . ?
O1 C1 C8 C9 1.8(5) . . . . ?
O1 C1 C8 C7 -177.6(3) . . . . ?
O1 C2 C10 C15 158.5(3) . . . . ?
O1 C2 C10 C11 -21.5(5) . . . . ?
O1 C2 C3 C9 1.1(5) . . . . ?
C1 C8 C9 C4 179.0(3) . . . . ?
C1 O1 C2 C3 -0.4(5) . . . . ?
C1 O1 C2 C10 178.7(3) . . . . ?
C1 C8 C9 C3 -1.2(5) . . . . ?
C2 C3 C9 C4 179.5(4) . . . . ?
C2 C3 C9 C8 -0.3(5) . . . . ?
C2 C10 C11 C12 -179.1(4) . . . . ?
C2 O1 C1 C8 -1.0(5) . . . . ?
C2 O1 C1 S1 178.0(2) . . . . ?
C2 C10 C15 C14 179.8(4) . . . . ?
C3 C2 C10 C15 -22.5(6) . . . . ?
C3 C2 C10 C11 157.6(4) . . . . ?
C4 C5 C6 C7 -0.6(7) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C5 C4 C9 C8 0.7(6) . . . . ?
C5 C4 C9 C3 -179.1(4) . . . . ?
C6 C7 C8 C9 1.4(6) . . . . ?
C6 C7 C8 C1 -179.2(4) . . . . ?
C7 C8 C9 C4 -1.6(5) . . . . ?
C7 C8 C9 C3 178.2(3) . . . . ?
C9 C4 C5 C6 0.4(6) . . . . ?
C10 C2 C3 C9 -177.9(3) . . . . ?
C10 C11 C12 C13 -1.3(7) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C11 C10 C15 C14 -0.2(6) . . . . ?
C12 C13 C14 C15 -0.4(7) . . . . ?
C13 C14 C15 C10 0.0(6) . . . . ?
C15 C10 C11 C12 0.9(6) . . . . ?

#===END


