# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
#TrackingRef '- ccdc_deposit of 13.cif'

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2011-02-14
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

#==============================================================================
#
# SUBMISSION DETAILS

_publ_contact_author_name        'Dipakranjan Mal'
# Name of author for correspondence 'Dipakranjan Mal'

_publ_contact_author_address     
;Department of Chemistry
Indian Institute of Technology Kharagpur
Kharagpur
West Bengal, India
;
# Address of author for correspondence

_publ_contact_author_email       dmal@chem.iitkgp.ernet.in
_publ_contact_author_fax         00(000)0000000
_publ_contact_author_phone       '+91 - 3222 - 283318'

_publ_contact_letter             
;
Submission dated :2011-11-10

Please consider this CIF for submission to the Cambridge Crystallographic
Data Centre. I certify that all authors have seen and approved of this
submission, that all have made significant scientific contributions to the
work reported, and that all share responsibility and accountability for
the results.

This CIF is submitted as a personal communication

This CIF is submitted as part of a journal submission
<Insert Journal details here>

Bloggs, Joe J.
;

#==============================================================================
#
# TITLE AND AUTHOR LIST

_publ_section_title              
; ?
;
_publ_section_title_footnote     
; ?
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
#<--'Last name, first name'
'Dipak Mal'
; ?
;
;Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
'Prithiba Mitra' '' ''
'Brateen Shome' '' ''
'Saroj De' '' ''
'Anindya Sarkar' '' ''

#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_14jandm
_database_code_depnum_ccdc_archive 'CCDC 855857'
#TrackingRef '- ccdc_deposit of 13.cif'

_audit_creation_date             2011-02-14T23:57:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/c
_symmetry_space_group_name_Hall  -p2ybc
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.257(2)
_cell_length_b                   5.2096(9)
_cell_length_c                   22.234(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.886(8)
_cell_angle_gamma                90
_cell_volume                     1260.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_number            7767
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_full        28.39
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_reflns_number_total             3067
_reflns_number_gt                2244
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0935P)^2^+0.9021P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3067
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.2047
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.104

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.09040(19) -0.2155(4) 0.02261(10) 0.0225(4) Uani 1 1 d . . .
C2 C -0.16472(18) -0.0017(4) 0.03972(9) 0.0208(4) Uani 1 1 d . . .
C3 C -0.2818(2) 0.0403(4) 0.00062(10) 0.0260(5) Uani 1 1 d . . .
H3 H -0.3101 -0.0649 -0.0339 0.031 Uiso 1 1 calc R . .
C4 C -0.3566(2) 0.2349(5) 0.01216(10) 0.0282(5) Uani 1 1 d . . .
H4A H -0.4345 0.2598 -0.0141 0.034 Uiso 1 1 calc R . .
C5 C -0.31364(19) 0.3924(4) 0.06338(10) 0.0243(5) Uani 1 1 d . . .
H5 H -0.3628 0.525 0.0713 0.029 Uiso 1 1 calc R . .
C6 C -0.1987(2) 0.3536(4) 0.10254(9) 0.0238(5) Uani 1 1 d . . .
H6 H -0.1718 0.4611 0.1367 0.029 Uiso 1 1 calc R . .
C7 C -0.12030(19) 0.1560(4) 0.09247(9) 0.0217(4) Uani 1 1 d . . .
C8 C 0.0007(2) 0.1209(4) 0.13666(10) 0.0271(5) Uani 1 1 d . . .
H8 H 0.0433 -0.0278 0.1322 0.033 Uiso 1 1 calc R . .
C9 C 0.0551(2) 0.2777(4) 0.18186(10) 0.0252(5) Uani 1 1 d . . .
H9 H 0.0129 0.4272 0.1862 0.03 Uiso 1 1 calc R . .
C10 C 0.17505(19) 0.2405(4) 0.22590(10) 0.0219(4) Uani 1 1 d . . .
C11 C 0.25609(19) 0.0424(4) 0.22134(10) 0.0241(5) Uani 1 1 d . . .
H11 H 0.2329 -0.0758 0.1891 0.029 Uiso 1 1 calc R . .
C12 C 0.36987(19) 0.0169(4) 0.26341(10) 0.0245(5) Uani 1 1 d . . .
H12 H 0.4221 -0.1163 0.2591 0.029 Uiso 1 1 calc R . .
C13 C 0.40608(19) 0.1915(4) 0.31227(9) 0.0229(5) Uani 1 1 d . . .
C14 C 0.32697(19) 0.3892(4) 0.31803(10) 0.0249(5) Uani 1 1 d . . .
H14 H 0.3501 0.5056 0.3507 0.03 Uiso 1 1 calc R . .
C15 C 0.21404(19) 0.4136(4) 0.27546(10) 0.0243(5) Uani 1 1 d . . .
H15 H 0.1625 0.5481 0.2798 0.029 Uiso 1 1 calc R . .
C16 C 0.5984(2) -0.0180(5) 0.35330(11) 0.0318(5) Uani 1 1 d . . .
H16A H 0.6708 -0.0025 0.3872 0.048 Uiso 1 1 calc R . .
H16B H 0.6209 -0.0081 0.3145 0.048 Uiso 1 1 calc R . .
H16C H 0.5596 -0.1801 0.356 0.048 Uiso 1 1 calc R . .
O1 O -0.14642(14) -0.3356(3) -0.02890(7) 0.0294(4) Uani 1 1 d . . .
H2 H -0.1019 -0.45 -0.036 0.035 Uiso 1 1 d R . .
O2 O 0.01305(14) -0.2753(3) 0.05273(8) 0.0308(4) Uani 1 1 d . . .
O3 O 0.51529(14) 0.1849(3) 0.35658(7) 0.0271(4) 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 0.0206(10) 0.0242(10) 0.0228(10) -0.0005(8) 0.0060(8) -0.0027(8)
C2 0.0179(9) 0.0227(10) 0.0225(10) 0.0031(8) 0.0062(8) -0.0003(8)
C3 0.0265(11) 0.0259(11) 0.0237(10) -0.0018(8) 0.0029(8) -0.0003(9)
C4 0.0237(11) 0.0317(12) 0.0258(11) 0.0030(9) -0.0001(9) 0.0019(9)
C5 0.0227(10) 0.0236(10) 0.0268(11) 0.0045(8) 0.0066(8) 0.0054(8)
C6 0.0261(11) 0.0255(11) 0.0189(10) -0.0005(8) 0.0040(8) 0.0019(8)
C7 0.0230(10) 0.0225(10) 0.0190(10) 0.0020(8) 0.0047(8) -0.0003(8)
C8 0.0235(10) 0.0306(12) 0.0250(11) -0.0050(9) 0.0022(9) 0.0076(9)
C9 0.0210(10) 0.0228(11) 0.0299(11) -0.0006(8) 0.0034(9) 0.0037(8)
C10 0.0201(10) 0.0220(10) 0.0235(10) 0.0027(8) 0.0051(8) -0.0013(8)
C11 0.0234(10) 0.0238(10) 0.0237(10) -0.0034(8) 0.0033(8) -0.0015(8)
C12 0.0234(10) 0.0235(10) 0.0257(10) 0.0014(8) 0.0044(8) 0.0054(8)
C13 0.0193(10) 0.0276(11) 0.0208(10) 0.0035(8) 0.0033(8) -0.0007(8)
C14 0.0246(11) 0.0263(11) 0.0228(10) -0.0051(8) 0.0044(8) -0.0026(8)
C15 0.0206(10) 0.0232(10) 0.0288(11) -0.0027(8) 0.0061(8) 0.0008(8)
C16 0.0261(11) 0.0343(13) 0.0309(12) 0.0028(10) 0.0000(9) 0.0059(9)
O1 0.0256(8) 0.0335(9) 0.0268(8) -0.0093(7) 0.0021(6) 0.0028(7)
O2 0.0237(8) 0.0309(9) 0.0345(9) -0.0087(7) 0.0014(7) 0.0035(7)
O3 0.0205(8) 0.0346(9) 0.0237(8) -0.0011(6) 0.0009(6) 0.0031(6)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 O2 1.225(3) . ?
C1 O1 1.315(3) . ?
C1 C2 1.500(3) . ?
C2 C3 1.397(3) . ?
C2 C7 1.414(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.93 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.93 . ?
C5 C6 1.377(3) . ?
C5 H5 0.93 . ?
C6 C7 1.410(3) . ?
C6 H6 0.93 . ?
C7 C8 1.472(3) . ?
C8 C9 1.318(3) . ?
C8 H8 0.93 . ?
C9 C10 1.463(3) . ?
C9 H9 0.93 . ?
C10 C11 1.398(3) . ?
C10 C15 1.404(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.93 . ?
C12 C13 1.395(3) . ?
C12 H12 0.93 . ?
C13 O3 1.364(2) . ?
C13 C14 1.389(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 O3 1.426(3) . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
O1 H2 0.82 . ?

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
O2 C1 O1 122.1(2) . . ?
O2 C1 C2 124.34(19) . . ?
O1 C1 C2 113.60(18) . . ?
C3 C2 C7 120.09(19) . . ?
C3 C2 C1 117.19(18) . . ?
C7 C2 C1 122.72(18) . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 122.1(2) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 116.96(19) . . ?
C6 C7 C8 119.61(19) . . ?
C2 C7 C8 123.43(19) . . ?
C9 C8 C7 126.9(2) . . ?
C9 C8 H8 116.5 . . ?
C7 C8 H8 116.5 . . ?
C8 C9 C10 126.6(2) . . ?
C8 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C11 C10 C15 116.91(19) . . ?
C11 C10 C9 123.80(19) . . ?
C15 C10 C9 119.27(19) . . ?
C12 C11 C10 121.95(19) . . ?
C12 C11 H11 119 . . ?
C10 C11 H11 119 . . ?
C11 C12 C13 119.88(19) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
O3 C13 C14 115.60(18) . . ?
O3 C13 C12 125.10(19) . . ?
C14 C13 C12 119.29(19) . . ?
C15 C14 C13 120.25(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 121.7(2) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 O1 H2 109.5 . . ?
C13 O3 C16 117.58(17) . . ?

#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_17jancm
_database_code_depnum_ccdc_archive 'CCDC 855858'
#TrackingRef '- ccdc_deposit of 16.cif'

_audit_creation_date             2011-02-15T01:08:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C12 H12 O2 S'
_chemical_formula_sum            'C12 H12 O2 S'
_chemical_formula_weight         220.29

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   p-1
_symmetry_space_group_name_Hall  -p1
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2317(19)
_cell_length_b                   8.138(2)
_cell_length_c                   9.500(3)
_cell_angle_alpha                108.982(4)
_cell_angle_beta                 90.709(4)
_cell_angle_gamma                90.925(5)
_cell_volume                     528.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_number            3447
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.947
_reflns_number_total             2491
_reflns_number_gt                1866
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0627P)^2^+1.8270P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2491
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.068
_refine_ls_wR_factor_ref         0.2205
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.141

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.2305(5) 0.2906(5) 0.5714(4) 0.0200(7) Uani 1 1 d . . .
C2 C 0.2270(5) 0.4638(5) 0.5600(4) 0.0189(7) Uani 1 1 d . . .
C3 C 0.1672(5) 0.6004(5) 0.6815(4) 0.0229(8) Uani 1 1 d . . .
H011 H 0.1301 0.5795 0.7677 0.027 Uiso 1 1 calc R . .
C4 C 0.1634(5) 0.7664(5) 0.6733(5) 0.0272(9) Uani 1 1 d . . .
H008 H 0.1256 0.8583 0.7544 0.033 Uiso 1 1 calc R . .
C5 C 0.2165(5) 0.7958(5) 0.5428(5) 0.0264(9) Uani 1 1 d . . .
H009 H 0.2117 0.9075 0.5368 0.032 Uiso 1 1 calc R . .
C6 C 0.2761(5) 0.6615(5) 0.4226(5) 0.0248(8) Uani 1 1 d . . .
H5 H 0.3124 0.6843 0.3371 0.03 Uiso 1 1 calc R . .
C7 C 0.2830(5) 0.4922(5) 0.4268(4) 0.0210(8) Uani 1 1 d . . .
C8 C 0.3430(5) 0.3445(5) 0.3056(4) 0.0204(7) Uani 1 1 d . . .
C9 C 0.3460(5) 0.1863(5) 0.3195(4) 0.0233(8) Uani 1 1 d . . .
C10 C 0.3971(6) 0.0165(5) 0.2081(5) 0.0272(9) Uani 1 1 d . . .
H5R1 H 0.4692 -0.0487 0.2577 0.033 Uiso 1 1 calc R . .
H5R2 H 0.4736 0.0384 0.1327 0.033 Uiso 1 1 calc R . .
C11 C 0.2265(6) -0.0924(5) 0.1329(5) 0.0314(9) Uani 1 1 d . . .
H6R1 H 0.2651 -0.2005 0.0635 0.047 Uiso 1 1 calc R . .
H6R2 H 0.1567 -0.0299 0.0811 0.047 Uiso 1 1 calc R . .
H6R3 H 0.1507 -0.1151 0.2071 0.047 Uiso 1 1 calc R . .
C12 C 0.2035(6) 0.3881(6) 0.0455(5) 0.0307(9) Uani 1 1 d . . .
H2W1 H 0.2274 0.4038 -0.0485 0.046 Uiso 1 1 calc R . .
H2W2 H 0.1358 0.485 0.1069 0.046 Uiso 1 1 calc R . .
H2W3 H 0.1321 0.2829 0.0295 0.046 Uiso 1 1 calc R . .
O1 O 0.2904(4) 0.1595(3) 0.4480(3) 0.0236(6) Uani 1 1 d . . .
O2 O 0.1877(4) 0.2488(4) 0.6785(3) 0.0283(7) Uani 1 1 d . . .
S1 S 0.42115(14) 0.37414(14) 0.13757(12) 0.0279(3) 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 0.0194(17) 0.0213(18) 0.0188(18) 0.0060(14) -0.0027(13) -0.0033(14)
C2 0.0177(16) 0.0229(18) 0.0167(17) 0.0075(14) -0.0049(13) -0.0041(13)
C3 0.0197(17) 0.0266(19) 0.0217(19) 0.0070(15) 0.0005(14) 0.0010(14)
C4 0.0224(19) 0.0232(19) 0.030(2) 0.0002(16) -0.0015(16) 0.0048(15)
C5 0.0247(19) 0.0205(19) 0.034(2) 0.0100(16) -0.0092(16) -0.0044(15)
C6 0.0216(18) 0.026(2) 0.031(2) 0.0161(17) -0.0038(15) -0.0046(15)
C7 0.0158(16) 0.0225(18) 0.0245(19) 0.0081(15) -0.0114(14) -0.0054(13)
C8 0.0178(17) 0.0239(18) 0.0197(18) 0.0075(14) 0.0023(13) -0.0007(14)
C9 0.0188(17) 0.028(2) 0.0224(19) 0.0071(15) -0.0008(14) 0.0002(14)
C10 0.028(2) 0.026(2) 0.025(2) 0.0046(16) 0.0010(16) 0.0043(16)
C11 0.036(2) 0.026(2) 0.027(2) 0.0017(17) -0.0048(17) 0.0027(17)
C12 0.028(2) 0.040(2) 0.027(2) 0.0152(18) -0.0061(17) -0.0025(18)
O1 0.0281(14) 0.0182(13) 0.0233(14) 0.0051(11) 0.0010(11) -0.0008(10)
O2 0.0399(17) 0.0274(15) 0.0198(14) 0.0108(12) 0.0025(12) -0.0031(12)
S1 0.0241(5) 0.0382(6) 0.0239(5) 0.0136(4) 0.0011(4) -0.0002(4)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 O2 1.215(5) . ?
C1 O1 1.383(5) . ?
C1 C2 1.449(5) . ?
C2 C3 1.395(5) . ?
C2 C7 1.420(5) . ?
C3 C4 1.379(6) . ?
C4 C5 1.394(6) . ?
C5 C6 1.378(6) . ?
C6 C7 1.393(5) . ?
C7 C8 1.445(5) . ?
C8 C9 1.337(6) . ?
C8 S1 1.787(4) . ?
C9 O1 1.371(5) . ?
C9 C10 1.496(5) . ?
C10 C11 1.533(6) . ?
C12 S1 1.814(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 116.7(3) . . ?
O2 C1 C2 126.7(4) . . ?
O1 C1 C2 116.6(3) . . ?
C3 C2 C7 121.2(3) . . ?
C3 C2 C1 118.8(3) . . ?
C7 C2 C1 120.1(3) . . ?
C4 C3 C2 119.7(4) . . ?
C3 C4 C5 119.7(4) . . ?
C6 C5 C4 120.8(4) . . ?
C5 C6 C7 121.2(4) . . ?
C6 C7 C2 117.4(4) . . ?
C6 C7 C8 124.5(4) . . ?
C2 C7 C8 118.1(3) . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 S1 119.5(3) . . ?
C7 C8 S1 119.9(3) . . ?
C8 C9 O1 121.1(3) . . ?
C8 C9 C10 129.4(4) . . ?
O1 C9 C10 109.5(3) . . ?
C9 C10 C11 112.1(3) . . ?
C9 O1 C1 123.6(3) . . ?
C8 S1 C12 101.41(19) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
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# END of CIF