# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx2895a
_database_code_depnum_ccdc_archive 'CCDC 993221'
_audit_update_record             
;
2014-03-24 deposited with the CCDC.
2015-05-21 downloaded from the CCDC.
;
_audit_creation_date             2014-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H23 Cl O5 S'
_chemical_formula_sum            'C24 H23 Cl O5 S'
_chemical_formula_weight         458.93
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.750(2)
_cell_length_b                   11.792(3)
_cell_length_c                   12.599(3)
_cell_angle_alpha                63.166(11)
_cell_angle_beta                 74.738(14)
_cell_angle_gamma                83.873(16)
_cell_volume                     1118.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3358
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4824
_cell_measurement_theta_min      1.8672
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9383
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         1.867
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             5130
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0057
_diffrn_orient_matrix_UB_12      -0.0999
_diffrn_orient_matrix_UB_13      0.0635
_diffrn_orient_matrix_UB_21      -0.0933
_diffrn_orient_matrix_UB_22      -0.0068
_diffrn_orient_matrix_UB_23      -0.0166
_diffrn_orient_matrix_UB_31      0.0552
_diffrn_orient_matrix_UB_32      -0.0213
_diffrn_orient_matrix_UB_33      -0.0700
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3462
_reflns_number_total             4014
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4014
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0975
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1115P)²+2.1461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2423
_refine_ls_wR_factor_ref         0.2535
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24-C23
 1.54 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C20(H20A,H20B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.89375(19) 0.15036(14) -0.04068(14) 0.0758(5) Uani 1 1 d . . . . .
S1 S 0.35604(14) 0.47646(11) 0.38220(12) 0.0470(4) Uani 1 1 d . . . . .
O1 O 0.3865(4) 0.2439(3) 0.3717(4) 0.0621(10) Uani 1 1 d . . . . .
O2 O 0.7718(4) 0.6594(3) 0.2927(3) 0.0500(8) Uani 1 1 d . . . . .
O3 O 0.8484(4) 0.5412(3) 0.1895(3) 0.0508(9) Uani 1 1 d . . . . .
O4 O 0.5717(5) 0.6560(4) -0.0068(4) 0.0670(11) Uani 1 1 d . . . . .
O5 O 0.7274(6) 0.7799(4) 0.0086(3) 0.0774(13) Uani 1 1 d . . . . .
C1 C 0.5906(5) 0.1741(4) 0.2479(4) 0.0438(11) Uani 1 1 d . . . . .
C2 C 0.6945(6) 0.2078(4) 0.1330(5) 0.0485(12) Uani 1 1 d . . . . .
H2 H 0.7131 0.2928 0.0767 0.058 Uiso 1 1 calc R . . . .
C3 C 0.7701(6) 0.1110(4) 0.1043(5) 0.0463(11) Uani 1 1 d . . . . .
C4 C 0.7488(6) -0.0135(4) 0.1891(5) 0.0478(11) Uani 1 1 d . . . . .
H4 H 0.8029 -0.0770 0.1705 0.057 Uiso 1 1 calc R . . . .
C5 C 0.6452(6) -0.0447(5) 0.3039(5) 0.0530(12) Uani 1 1 d . . . . .
H5 H 0.6317 -0.1290 0.3625 0.064 Uiso 1 1 calc R . . . .
C6 C 0.5637(6) 0.0486(5) 0.3304(5) 0.0485(11) Uani 1 1 d . . . . .
H6 H 0.4895 0.0268 0.4048 0.058 Uiso 1 1 calc R . . . .
C7 C 0.5015(6) 0.2751(5) 0.2828(5) 0.0465(11) Uani 1 1 d . . . . .
C8 C 0.5625(6) 0.4022(4) 0.2166(5) 0.0500(12) Uani 1 1 d . . . . .
H8 H 0.6406 0.4237 0.1441 0.060 Uiso 1 1 calc R . . . .
C9 C 0.5099(6) 0.4940(4) 0.2560(4) 0.0431(11) Uani 1 1 d . . . . .
C10 C 0.5904(6) 0.6241(4) 0.1949(4) 0.0422(10) Uani 1 1 d . . . . .
C11 C 0.4732(6) 0.7092(4) 0.2409(4) 0.0451(11) Uani 1 1 d . . . . .
H11A H 0.5288 0.7819 0.2305 0.054 Uiso 1 1 calc R . . . .
H11B H 0.3925 0.7401 0.1947 0.054 Uiso 1 1 calc R . . . .
C12 C 0.3983(6) 0.6298(4) 0.3748(5) 0.0450(11) Uani 1 1 d . . . . .
H12 H 0.4773 0.6164 0.4218 0.054 Uiso 1 1 calc R . . . .
C13 C 0.2545(5) 0.6905(4) 0.4249(4) 0.0423(10) Uani 1 1 d . . . . .
C14 C 0.1082(6) 0.6948(5) 0.4006(5) 0.0503(12) Uani 1 1 d . . . . .
H14 H 0.0938 0.6555 0.3544 0.060 Uiso 1 1 calc R . . . .
C15 C -0.0170(6) 0.7572(5) 0.4442(5) 0.0561(13) Uani 1 1 d . . . . .
H15 H -0.1150 0.7587 0.4278 0.067 Uiso 1 1 calc R . . . .
C16 C 0.0029(6) 0.8173(5) 0.5121(5) 0.0560(13) Uani 1 1 d . . . . .
H16 H -0.0810 0.8593 0.5414 0.067 Uiso 1 1 calc R . . . .
C17 C 0.1488(6) 0.8140(5) 0.5357(5) 0.0539(13) Uani 1 1 d . . . . .
H17 H 0.1642 0.8553 0.5799 0.065 Uiso 1 1 calc R . . . .
C18 C 0.2716(6) 0.7499(4) 0.4943(5) 0.0469(11) Uani 1 1 d . . . . .
H18 H 0.3684 0.7464 0.5132 0.056 Uiso 1 1 calc R . . . .
C19 C 0.7450(5) 0.6116(4) 0.2332(4) 0.0395(10) Uani 1 1 d . . . . .
C20 C 0.9974(6) 0.5120(5) 0.2261(5) 0.0493(12) Uani 1 1 d . . . . .
H20A H 0.9787 0.4610 0.3140 0.059 Uiso 1 1 calc R . . . .
H20B H 1.0525 0.5897 0.2038 0.059 Uiso 1 1 calc R . . . .
C21 C 1.0923(7) 0.4408(7) 0.1609(7) 0.0744(17) Uani 1 1 d . . . . .
H21A H 1.1033 0.4898 0.0742 0.112 Uiso 1 1 calc GR . . . .
H21B H 1.0400 0.3614 0.1881 0.112 Uiso 1 1 calc GR . . . .
H21C H 1.1952 0.4248 0.1779 0.112 Uiso 1 1 calc GR . . . .
C22 C 0.6269(7) 0.6871(5) 0.0536(5) 0.0508(12) Uani 1 1 d . . . . .
C23 C 0.7811(12) 0.8562(7) -0.1292(7) 0.104(3) Uani 1 1 d D . . . .
H23A H 0.8934 0.8768 -0.1547 0.125 Uiso 1 1 calc R . . . .
H23B H 0.7592 0.8110 -0.1717 0.125 Uiso 1 1 calc R . . . .
C24 C 0.6858(11) 0.9694(9) -0.1506(8) 0.111(3) Uani 1 1 d D . . . .
H24A H 0.7146 1.0281 -0.2359 0.167 Uiso 1 1 calc GR . . . .
H24B H 0.7038 1.0083 -0.1024 0.167 Uiso 1 1 calc GR . . . .
H24C H 0.5757 0.9465 -0.1276 0.167 Uiso 1 1 calc GR . . . .


_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
Cl1 C3 1.739(5) . ?
S1 C9 1.738(5) . ?
S1 C12 1.840(5) . ?
O1 C7 1.231(6) . ?
O2 C19 1.198(5) . ?
O3 C19 1.342(5) . ?
O3 C20 1.452(6) . ?
O4 C22 1.196(6) . ?
O5 C22 1.294(7) . ?
O5 C23 1.515(8) . ?
C1 C2 1.396(7) . ?
C1 C6 1.372(7) . ?
C1 C7 1.521(7) . ?
C2 C3 1.399(7) . ?
C3 C4 1.368(7) . ?
C4 C5 1.396(7) . ?
C5 C6 1.367(7) . ?
C7 C8 1.426(7) . ?
C8 C9 1.374(7) . ?
C9 C10 1.523(6) . ?
C10 C11 1.545(6) . ?
C10 C19 1.524(6) . ?
C10 C22 1.543(7) . ?
C11 C12 1.508(7) . ?
C12 C13 1.513(6) . ?
C13 C14 1.383(7) . ?
C13 C18 1.387(7) . ?
C14 C15 1.385(7) . ?
C15 C16 1.385(8) . ?
C16 C17 1.378(7) . ?
C17 C18 1.372(7) . ?
C20 C21 1.478(7) . ?
C23 C24 1.451(8) . ?

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
C9 S1 C12 93.7(2) . . ?
C19 O3 C20 117.4(3) . . ?
C22 O5 C23 119.4(5) . . ?
C2 C1 C7 120.8(4) . . ?
C6 C1 C2 120.4(4) . . ?
C6 C1 C7 118.8(4) . . ?
C1 C2 C3 118.5(4) . . ?
C2 C3 Cl1 119.3(4) . . ?
C4 C3 Cl1 119.9(4) . . ?
C4 C3 C2 120.8(5) . . ?
C3 C4 C5 119.5(5) . . ?
C6 C5 C4 120.1(5) . . ?
C5 C6 C1 120.5(5) . . ?
O1 C7 C1 119.6(4) . . ?
O1 C7 C8 122.0(5) . . ?
C8 C7 C1 118.2(4) . . ?
C9 C8 C7 122.4(5) . . ?
C8 C9 S1 125.9(4) . . ?
C8 C9 C10 122.2(5) . . ?
C10 C9 S1 111.8(3) . . ?
C9 C10 C11 106.0(4) . . ?
C9 C10 C19 109.3(4) . . ?
C9 C10 C22 114.0(4) . . ?
C19 C10 C11 110.9(4) . . ?
C19 C10 C22 108.5(4) . . ?
C22 C10 C11 108.2(4) . . ?
C12 C11 C10 107.6(4) . . ?
C11 C12 S1 103.8(3) . . ?
C11 C12 C13 113.3(4) . . ?
C13 C12 S1 114.0(3) . . ?
C14 C13 C12 123.5(4) . . ?
C14 C13 C18 118.0(4) . . ?
C18 C13 C12 118.5(4) . . ?
C13 C14 C15 120.8(5) . . ?
C16 C15 C14 120.4(5) . . ?
C17 C16 C15 119.0(5) . . ?
C18 C17 C16 120.4(5) . . ?
C17 C18 C13 121.5(5) . . ?
O2 C19 O3 124.5(4) . . ?
O2 C19 C10 124.8(4) . . ?
O3 C19 C10 110.7(4) . . ?
O3 C20 C21 106.7(4) . . ?
O4 C22 O5 124.2(5) . . ?
O4 C22 C10 125.8(5) . . ?
O5 C22 C10 109.9(4) . . ?
C24 C23 O5 102.0(7) . . ?

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
Cl1 C3 C4 C5 -177.9(4) . . . . ?
S1 C9 C10 C11 -18.0(4) . . . . ?
S1 C9 C10 C19 101.5(4) . . . . ?
S1 C9 C10 C22 -136.9(4) . . . . ?
S1 C12 C13 C14 -43.0(6) . . . . ?
S1 C12 C13 C18 139.9(4) . . . . ?
O1 C7 C8 C9 8.1(8) . . . . ?
C1 C2 C3 Cl1 177.4(4) . . . . ?
C1 C2 C3 C4 -3.2(7) . . . . ?
C1 C7 C8 C9 -166.9(4) . . . . ?
C2 C1 C6 C5 3.9(7) . . . . ?
C2 C1 C7 O1 164.1(5) . . . . ?
C2 C1 C7 C8 -20.8(7) . . . . ?
C2 C3 C4 C5 2.7(7) . . . . ?
C3 C4 C5 C6 1.1(8) . . . . ?
C4 C5 C6 C1 -4.4(8) . . . . ?
C6 C1 C2 C3 -0.1(7) . . . . ?
C6 C1 C7 O1 -14.0(7) . . . . ?
C6 C1 C7 C8 161.0(5) . . . . ?
C7 C1 C2 C3 -178.2(4) . . . . ?
C7 C1 C6 C5 -177.9(4) . . . . ?
C7 C8 C9 S1 -4.8(7) . . . . ?
C7 C8 C9 C10 171.5(4) . . . . ?
C8 C9 C10 C11 165.2(4) . . . . ?
C8 C9 C10 C19 -75.2(5) . . . . ?
C8 C9 C10 C22 46.3(6) . . . . ?
C9 S1 C12 C11 27.9(3) . . . . ?
C9 S1 C12 C13 151.6(4) . . . . ?
C9 C10 C11 C12 39.4(5) . . . . ?
C9 C10 C19 O2 -115.3(5) . . . . ?
C9 C10 C19 O3 65.7(5) . . . . ?
C9 C10 C22 O4 15.6(7) . . . . ?
C9 C10 C22 O5 -164.4(4) . . . . ?
C10 C11 C12 S1 -42.5(4) . . . . ?
C10 C11 C12 C13 -166.7(4) . . . . ?
C11 C10 C19 O2 1.1(6) . . . . ?
C11 C10 C19 O3 -177.9(4) . . . . ?
C11 C10 C22 O4 -102.0(6) . . . . ?
C11 C10 C22 O5 78.0(5) . . . . ?
C11 C12 C13 C14 75.4(6) . . . . ?
C11 C12 C13 C18 -101.6(5) . . . . ?
C12 S1 C9 C8 171.0(4) . . . . ?
C12 S1 C9 C10 -5.6(4) . . . . ?
C12 C13 C14 C15 -176.8(5) . . . . ?
C12 C13 C18 C17 175.7(4) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C14 C13 C18 C17 -1.5(7) . . . . ?
C14 C15 C16 C17 -0.1(8) . . . . ?
C15 C16 C17 C18 -1.2(8) . . . . ?
C16 C17 C18 C13 2.0(8) . . . . ?
C18 C13 C14 C15 0.2(7) . . . . ?
C19 O3 C20 C21 -176.9(4) . . . . ?
C19 C10 C11 C12 -79.0(5) . . . . ?
C19 C10 C22 O4 137.6(5) . . . . ?
C19 C10 C22 O5 -42.4(5) . . . . ?
C20 O3 C19 O2 5.7(7) . . . . ?
C20 O3 C19 C10 -175.3(4) . . . . ?
C22 O5 C23 C24 100.9(8) . . . . ?
C22 C10 C11 C12 162.1(4) . . . . ?
C22 C10 C19 O2 119.8(5) . . . . ?
C22 C10 C19 O3 -59.1(5) . . . . ?
C23 O5 C22 O4 0.0(9) . . . . ?
C23 O5 C22 C10 -180.0(5) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1041149'
_audit_update_record             
;
2014-12-25 deposited with the CCDC.
2015-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 O5 S2'
_chemical_formula_weight         430.52

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   I2/c

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

_cell_length_a                   16.4871(5)
_cell_length_b                   12.8345(3)
_cell_length_c                   21.2978(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.389(4)
_cell_angle_gamma                90.00
_cell_volume                     4167.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8391
_cell_measurement_theta_min      4.2900
_cell_measurement_theta_max      73.7200

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.3376
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11485
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.42
_reflns_number_total             4170
_reflns_number_gt                4077
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0440P)²+15.3220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4170
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13265(4) 0.69751(4) 0.27041(3) 0.01714(15) Uani 1 1 d . . .
S2 S 0.21669(4) 0.45024(5) 0.50940(3) 0.02179(16) Uani 1 1 d . . .
O1 O 0.26452(12) 0.57268(13) 0.16672(9) 0.0228(4) Uani 1 1 d . . .
O2 O 0.25571(10) 0.42711(12) 0.22224(8) 0.0175(3) Uani 1 1 d . . .
O3 O 0.01813(11) 0.40875(14) 0.17369(9) 0.0234(4) Uani 1 1 d . . .
O4 O 0.08454(11) 0.41516(14) 0.09872(8) 0.0225(4) Uani 1 1 d . . .
O5 O 0.15753(11) 0.60351(13) 0.39549(8) 0.0211(4) Uani 1 1 d . . .
C1 C -0.00061(18) 1.0118(2) 0.09322(13) 0.0277(6) Uani 1 1 d . . .
H1 H -0.0297 1.0733 0.0713 0.033 Uiso 1 1 calc R . .
C2 C -0.03965(17) 0.9460(2) 0.12547(14) 0.0274(6) Uani 1 1 d . . .
H2 H -0.0957 0.9625 0.1258 0.033 Uiso 1 1 calc R . .
C3 C 0.00383(17) 0.8553(2) 0.15748(13) 0.0249(5) Uani 1 1 d . . .
H3 H -0.0228 0.8103 0.1795 0.030 Uiso 1 1 calc R . .
C4 C 0.08534(17) 0.83092(19) 0.15713(12) 0.0219(5) Uani 1 1 d . . .
C5 C 0.12356(16) 0.8968(2) 0.12528(13) 0.0234(5) Uani 1 1 d . . .
H5 H 0.1797 0.8805 0.1252 0.028 Uiso 1 1 calc R . .
C6 C 0.08093(18) 0.9866(2) 0.09337(14) 0.0281(6) Uani 1 1 d . . .
H6 H 0.1080 1.0311 0.0714 0.034 Uiso 1 1 calc R . .
C7 C 0.13282(15) 0.7299(2) 0.18622(12) 0.0215(5) Uani 1 1 d . . .
H7 H 0.1950 0.7362 0.1902 0.026 Uiso 1 1 calc R . .
C8 C 0.13699(14) 0.56368(18) 0.25830(11) 0.0166(4) Uani 1 1 d . . .
C9 C 0.13106(15) 0.53837(18) 0.18625(11) 0.0165(5) Uani 1 1 d . . .
C10 C 0.09215(16) 0.63518(18) 0.14312(12) 0.0201(5) Uani 1 1 d . . .
H10A H 0.1057 0.6348 0.1016 0.024 Uiso 1 1 calc R . .
H10B H 0.0276 0.6362 0.1294 0.024 Uiso 1 1 calc R . .
C11 C 0.22440(15) 0.51635(17) 0.18951(11) 0.0164(5) Uani 1 1 d . . .
C12 C 0.34558(15) 0.40264(19) 0.23085(13) 0.0212(5) Uani 1 1 d . . .
H12A H 0.3854 0.4602 0.2546 0.025 Uiso 1 1 calc R . .
H12B H 0.3497 0.3920 0.1861 0.025 Uiso 1 1 calc R . .
C13 C 0.37010(17) 0.3045(2) 0.27231(14) 0.0268(6) Uani 1 1 d . . .
H13A H 0.3291 0.2487 0.2488 0.040 Uiso 1 1 calc R . .
H13B H 0.3673 0.3167 0.3169 0.040 Uiso 1 1 calc R . .
H13C H 0.4298 0.2840 0.2783 0.040 Uiso 1 1 calc R . .
C14 C 0.07132(15) 0.44551(18) 0.15442(11) 0.0179(5) Uani 1 1 d . . .
C15 C 0.02582(16) 0.3344(2) 0.05742(12) 0.0238(5) Uani 1 1 d . . .
H15A H -0.0287 0.3663 0.0249 0.029 Uiso 1 1 calc R . .
H15B H 0.0099 0.2854 0.0868 0.029 Uiso 1 1 calc R . .
C16 C 0.07310(17) 0.2778(2) 0.01990(13) 0.0253(5) Uani 1 1 d . . .
H16A H 0.0338 0.2261 -0.0105 0.038 Uiso 1 1 calc R . .
H16B H 0.1247 0.2426 0.0525 0.038 Uiso 1 1 calc R . .
H16C H 0.0917 0.3277 -0.0068 0.038 Uiso 1 1 calc R . .
C17 C 0.14750(16) 0.49026(19) 0.30571(12) 0.0198(5) Uani 1 1 d . . .
H17 H 0.1458 0.4192 0.2927 0.024 Uiso 1 1 calc R . .
C18 C 0.16137(14) 0.51363(18) 0.37588(12) 0.0174(5) Uani 1 1 d . . .
C19 C 0.18388(14) 0.42513(18) 0.42366(11) 0.0163(4) Uani 1 1 d . . .
C20 C 0.23063(16) 0.3206(2) 0.52828(12) 0.0223(5) Uani 1 1 d . . .
H20 H 0.2508 0.2938 0.5732 0.027 Uiso 1 1 calc R . .
C21 C 0.20977(16) 0.2599(2) 0.47203(13) 0.0235(5) Uani 1 1 d . . .
H21 H 0.2130 0.1860 0.4735 0.028 Uiso 1 1 calc R . .
C22 C 0.18256(16) 0.3182(2) 0.41063(12) 0.0226(5) Uani 1 1 d . . .
H22 H 0.1657 0.2885 0.3666 0.027 Uiso 1 1 calc R . .


_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 C8 1.742(2) . ?
S1 C7 1.842(3) . ?
S2 C20 1.706(3) . ?
S2 C19 1.726(2) . ?
O1 C11 1.200(3) . ?
O2 C11 1.338(3) . ?
O2 C12 1.456(3) . ?
O3 C14 1.198(3) . ?
O4 C14 1.343(3) . ?
O4 C15 1.461(3) . ?
O5 C18 1.237(3) . ?
C1 C6 1.381(4) . ?
C1 C2 1.391(4) . ?
C2 C3 1.400(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.378(4) . ?
C4 C7 1.519(3) . ?
C5 C6 1.385(4) . ?
C7 C10 1.517(3) . ?
C8 C17 1.343(3) . ?
C8 C9 1.535(3) . ?
C9 C14 1.530(3) . ?
C9 C10 1.533(3) . ?
C9 C11 1.540(3) . ?
C12 C13 1.503(3) . ?
C15 C16 1.500(3) . ?
C17 C18 1.454(3) . ?
C18 C19 1.475(3) . ?
C19 C22 1.398(3) . ?
C20 C21 1.359(4) . ?
C21 C22 1.423(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C7 93.62(11) . . ?
C20 S2 C19 91.55(12) . . ?
C11 O2 C12 114.99(18) . . ?
C14 O4 C15 116.37(19) . . ?
C6 C1 C2 119.3(2) . . ?
C1 C2 C3 119.8(2) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 C7 117.6(2) . . ?
C3 C4 C7 122.8(2) . . ?
C4 C5 C6 120.7(2) . . ?
C1 C6 C5 120.5(2) . . ?
C10 C7 C4 113.4(2) . . ?
C10 C7 S1 104.10(16) . . ?
C4 C7 S1 113.47(17) . . ?
C17 C8 C9 123.0(2) . . ?
C17 C8 S1 125.52(18) . . ?
C9 C8 S1 111.48(16) . . ?
C14 C9 C10 108.30(18) . . ?
C14 C9 C8 113.13(19) . . ?
C10 C9 C8 106.27(18) . . ?
C14 C9 C11 109.91(18) . . ?
C10 C9 C11 111.03(19) . . ?
C8 C9 C11 108.17(18) . . ?
C7 C10 C9 107.43(19) . . ?
O1 C11 O2 124.3(2) . . ?
O1 C11 C9 124.5(2) . . ?
O2 C11 C9 111.18(19) . . ?
O2 C12 C13 106.73(19) . . ?
O3 C14 O4 125.1(2) . . ?
O3 C14 C9 125.9(2) . . ?
O4 C14 C9 108.88(19) . . ?
O4 C15 C16 107.8(2) . . ?
C8 C17 C18 123.5(2) . . ?
O5 C18 C17 122.1(2) . . ?
O5 C18 C19 121.1(2) . . ?
C17 C18 C19 116.7(2) . . ?
C22 C19 C18 129.6(2) . . ?
C22 C19 S2 111.60(17) . . ?
C18 C19 S2 118.77(17) . . ?
C21 C20 S2 112.64(19) . . ?
C20 C21 C22 113.2(2) . . ?
C19 C22 C21 111.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.072
