# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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data_c:\data\has27\rechnung\has27

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 O4 S'
_chemical_formula_sum            'C17 H14 O4 S'
_chemical_formula_weight         314.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.2101(6)
_cell_length_b                   7.1147(2)
_cell_length_c                   15.2952(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.959(5)
_cell_angle_gamma                90.00
_cell_volume                     1401.94(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13566
_cell_measurement_theta_min      3.4278
_cell_measurement_theta_max      76.8776

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1946
_exptl_crystal_size_mid          0.1512
_exptl_crystal_size_min          0.0507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_process_details   
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16011
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         77.01
_reflns_number_total             2820
_reflns_number_gt                2765
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
;
_computing_data_reduction        
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0467P)^2^+0.6866P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2820
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.07731(9) 0.71318(18) 0.19600(9) 0.0188(3) Uani 1 1 d . . .
H1 H 0.0472 0.7996 0.2241 0.023 Uiso 1 1 calc R . .
C2 C 0.02787(10) 0.54400(17) 0.15768(9) 0.0187(3) Uani 1 1 d . . .
H2 H -0.0365 0.5155 0.1596 0.022 Uiso 1 1 calc R . .
C3 C 0.07148(9) 0.41577(18) 0.11648(9) 0.0182(3) Uani 1 1 d . . .
C7 C 0.01825(10) 0.23167(18) 0.07675(10) 0.0234(3) Uani 1 1 d . . .
H7A H 0.0573 0.1631 0.0473 0.035 Uiso 1 1 calc R . .
H7B H -0.0523 0.2558 0.0280 0.035 Uiso 1 1 calc R . .
H7C H 0.0152 0.1564 0.1291 0.035 Uiso 1 1 calc R . .
C4 C 0.16460(10) 0.46318(17) 0.11151(10) 0.0194(3) Uani 1 1 d . . .
H4 H 0.1942 0.3783 0.0821 0.023 Uiso 1 1 calc R . .
C5 C 0.21471(9) 0.63173(18) 0.14866(9) 0.0184(3) Uani 1 1 d . . .
H5 H 0.2775 0.6632 0.1442 0.022 Uiso 1 1 calc R . .
C6 C 0.17122(9) 0.75387(17) 0.19254(9) 0.0158(2) Uani 1 1 d . . .
S S 0.23505(2) 0.96952(4) 0.24505(2) 0.01595(10) Uani 1 1 d . . .
O1 O 0.29182(7) 1.03291(12) 0.18530(7) 0.0206(2) Uani 1 1 d . . .
C8 C 0.33508(9) 0.87694(16) 0.35225(9) 0.0153(2) Uani 1 1 d . . .
C9 C 0.30623(9) 0.84870(16) 0.43074(9) 0.0162(2) Uani 1 1 d . . .
O2 O 0.22006(7) 0.87558(13) 0.42646(7) 0.0215(2) Uani 1 1 d . . .
O3 O 0.38199(6) 0.78619(12) 0.51690(6) 0.01684(19) Uani 1 1 d . . .
C10 C 0.48109(9) 0.74684(17) 0.52626(9) 0.0155(2) Uani 1 1 d . . .
C11 C 0.55131(10) 0.67993(17) 0.61515(9) 0.0182(3) Uani 1 1 d . . .
H11 H 0.5313 0.6637 0.6666 0.022 Uiso 1 1 calc R . .
C12 C 0.65143(10) 0.63726(17) 0.62723(9) 0.0185(3) Uani 1 1 d . . .
H12 H 0.6998 0.5914 0.6879 0.022 Uiso 1 1 calc R . .
C13 C 0.68334(9) 0.65962(16) 0.55303(9) 0.0172(3) Uani 1 1 d . . .
C17 C 0.79277(9) 0.61196(19) 0.56830(10) 0.0222(3) Uani 1 1 d . . .
H17A H 0.7912 0.5467 0.5113 0.033 Uiso 1 1 calc R . .
H17B H 0.8248 0.5304 0.6249 0.033 Uiso 1 1 calc R . .
H17C H 0.8334 0.7279 0.5787 0.033 Uiso 1 1 calc R . .
C14 C 0.61203(9) 0.72878(17) 0.46494(9) 0.0162(2) Uani 1 1 d . . .
H14 H 0.6323 0.7461 0.4137 0.019 Uiso 1 1 calc R . .
C15 C 0.51041(9) 0.77325(16) 0.45091(9) 0.0149(2) Uani 1 1 d . . .
C16 C 0.43337(9) 0.84428(16) 0.36013(9) 0.0155(2) Uani 1 1 d . . .
O4 O 0.46291(7) 0.87378(14) 0.28988(7) 0.0213(2) Uani 1 1 d . . .
H1O4 H 0.4144 0.9252 0.2431 0.032 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0181(6) 0.0192(6) 0.0188(6) -0.0002(5) 0.0076(5) 0.0016(5)
C2 0.0164(6) 0.0201(6) 0.0186(6) 0.0025(5) 0.0064(5) -0.0013(5)
C3 0.0190(6) 0.0169(6) 0.0141(6) 0.0027(4) 0.0023(5) -0.0001(5)
C7 0.0233(6) 0.0181(6) 0.0230(7) 0.0005(5) 0.0040(5) -0.0022(5)
C4 0.0191(6) 0.0196(6) 0.0176(6) -0.0013(5) 0.0059(5) 0.0023(5)
C5 0.0153(5) 0.0209(6) 0.0172(6) 0.0000(5) 0.0050(5) 0.0005(5)
C6 0.0154(5) 0.0146(5) 0.0138(6) 0.0011(4) 0.0028(4) 0.0000(4)
S 0.01467(16) 0.01423(17) 0.01638(17) 0.00065(10) 0.00406(12) 0.00056(10)
O1 0.0194(4) 0.0210(5) 0.0195(5) 0.0050(3) 0.0062(4) -0.0017(3)
C8 0.0147(5) 0.0132(5) 0.0155(6) -0.0003(4) 0.0041(4) -0.0005(4)
C9 0.0164(6) 0.0125(5) 0.0184(6) -0.0020(4) 0.0060(5) -0.0015(4)
O2 0.0173(4) 0.0244(5) 0.0250(5) 0.0005(4) 0.0111(4) 0.0013(3)
O3 0.0166(4) 0.0186(4) 0.0166(5) 0.0004(3) 0.0083(3) 0.0001(3)
C10 0.0156(5) 0.0119(5) 0.0192(6) -0.0021(4) 0.0076(5) -0.0019(4)
C11 0.0224(6) 0.0153(6) 0.0166(6) -0.0002(4) 0.0079(5) -0.0027(5)
C12 0.0202(6) 0.0133(5) 0.0166(6) 0.0015(4) 0.0027(5) -0.0019(4)
C13 0.0161(6) 0.0117(5) 0.0206(6) -0.0008(4) 0.0046(5) -0.0019(4)
C17 0.0162(6) 0.0226(6) 0.0245(7) 0.0038(5) 0.0053(5) 0.0019(5)
C14 0.0165(5) 0.0142(6) 0.0175(6) -0.0006(4) 0.0068(5) -0.0017(4)
C15 0.0162(5) 0.0117(5) 0.0159(6) -0.0013(4) 0.0058(4) -0.0014(4)
C16 0.0175(6) 0.0135(5) 0.0156(6) -0.0017(4) 0.0072(5) -0.0017(4)
O4 0.0179(4) 0.0307(5) 0.0160(5) 0.0054(4) 0.0080(3) 0.0043(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3881(17) . ?
C1 C2 1.3923(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3940(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3984(18) . ?
C3 C7 1.5064(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C5 1.3880(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3920(17) . ?
C5 H5 0.9500 . ?
C6 S 1.7909(12) . ?
S O1 1.5204(9) . ?
S C8 1.7821(12) . ?
C8 C16 1.3701(16) . ?
C8 C9 1.4371(18) . ?
C9 O2 1.2135(15) . ?
C9 O3 1.3770(15) . ?
O3 C10 1.3826(14) . ?
C10 C11 1.3877(17) . ?
C10 C15 1.3938(18) . ?
C11 C12 1.3888(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3976(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3899(17) . ?
C13 C17 1.5103(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C14 C15 1.4034(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.4487(16) . ?
C16 O4 1.3250(15) . ?
O4 H1O4 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.13(12) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C1 C2 C3 120.96(12) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 118.57(12) . . ?
C2 C3 C7 120.53(12) . . ?
C4 C3 C7 120.89(12) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C4 C3 121.32(12) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.77(11) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 121.18(11) . . ?
C1 C6 S 118.34(10) . . ?
C5 C6 S 120.48(9) . . ?
O1 S C8 104.07(5) . . ?
O1 S C6 106.34(6) . . ?
C8 S C6 98.76(5) . . ?
C16 C8 C9 122.84(11) . . ?
C16 C8 S 122.10(10) . . ?
C9 C8 S 114.98(9) . . ?
O2 C9 O3 117.79(11) . . ?
O2 C9 C8 124.75(12) . . ?
O3 C9 C8 117.46(10) . . ?
C9 O3 C10 121.02(10) . . ?
O3 C10 C11 116.80(11) . . ?
O3 C10 C15 122.26(11) . . ?
C11 C10 C15 120.94(11) . . ?
C10 C11 C12 118.56(12) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C13 122.16(11) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 118.28(11) . . ?
C14 C13 C17 120.76(11) . . ?
C12 C13 C17 120.96(11) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C14 C15 120.69(11) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 119.37(11) . . ?
C10 C15 C16 118.08(11) . . ?
C14 C15 C16 122.55(11) . . ?
O4 C16 C8 124.18(11) . . ?
O4 C16 C15 117.55(10) . . ?
C8 C16 C15 118.27(11) . . ?
C16 O4 H1O4 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.20(19) . . . . ?
C1 C2 C3 C4 -2.05(19) . . . . ?
C1 C2 C3 C7 178.95(12) . . . . ?
C2 C3 C4 C5 1.58(19) . . . . ?
C7 C3 C4 C5 -179.43(12) . . . . ?
C3 C4 C5 C6 0.74(19) . . . . ?
C2 C1 C6 C5 2.21(19) . . . . ?
C2 C1 C6 S -178.41(9) . . . . ?
C4 C5 C6 C1 -2.67(19) . . . . ?
C4 C5 C6 S 177.96(9) . . . . ?
C1 C6 S O1 -147.67(10) . . . . ?
C5 C6 S O1 31.71(11) . . . . ?
C1 C6 S C8 104.78(10) . . . . ?
C5 C6 S C8 -75.84(11) . . . . ?
O1 S C8 C16 -11.31(11) . . . . ?
C6 S C8 C16 98.09(11) . . . . ?
O1 S C8 C9 165.63(9) . . . . ?
C6 S C8 C9 -84.97(10) . . . . ?
C16 C8 C9 O2 -179.80(12) . . . . ?
S C8 C9 O2 3.29(16) . . . . ?
C16 C8 C9 O3 0.04(17) . . . . ?
S C8 C9 O3 -176.86(8) . . . . ?
O2 C9 O3 C10 177.93(11) . . . . ?
C8 C9 O3 C10 -1.92(16) . . . . ?
C9 O3 C10 C11 -178.36(10) . . . . ?
C9 O3 C10 C15 1.96(17) . . . . ?
O3 C10 C11 C12 179.48(10) . . . . ?
C15 C10 C11 C12 -0.84(18) . . . . ?
C10 C11 C12 C13 0.02(18) . . . . ?
C11 C12 C13 C14 0.67(18) . . . . ?
C11 C12 C13 C17 -179.98(11) . . . . ?
C12 C13 C14 C15 -0.56(18) . . . . ?
C17 C13 C14 C15 -179.91(11) . . . . ?
O3 C10 C15 C14 -179.39(10) . . . . ?
C11 C10 C15 C14 0.95(18) . . . . ?
O3 C10 C15 C16 -0.07(18) . . . . ?
C11 C10 C15 C16 -179.73(11) . . . . ?
C13 C14 C15 C10 -0.23(18) . . . . ?
C13 C14 C15 C16 -179.52(11) . . . . ?
C9 C8 C16 O4 -178.13(11) . . . . ?
S C8 C16 O4 -1.44(17) . . . . ?
C9 C8 C16 C15 1.77(18) . . . . ?
S C8 C16 C15 178.46(8) . . . . ?
C10 C15 C16 O4 178.17(11) . . . . ?
C14 C15 C16 O4 -2.54(17) . . . . ?
C10 C15 C16 C8 -1.74(17) . . . . ?
C14 C15 C16 C8 177.56(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H1O4 O1 0.84 1.76 2.5435(12) 154.1 .

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        77.01
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 938546'