# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1575152'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H16 O5 S'
_chemical_formula_sum            'C16 H16 O5 S'
_chemical_formula_weight         320.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   8.1570(5)
_cell_length_b                   9.8595(7)
_cell_length_c                   10.2239(8)
_cell_angle_alpha                63.734(3)
_cell_angle_beta                 75.835(2)
_cell_angle_gamma                85.625(2)
_cell_volume                     714.45(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(1)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   SADABS
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33879
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.286
_diffrn_reflns_theta_max         30.583
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4395
_reflns_number_gt                3377
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.6312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4395
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_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
S1 S 0.30075(5) 0.17727(5) 0.42258(4) 0.01408(10) Uani 1 1 d . . . . .
O1 O 0.21191(16) 0.03890(14) 0.53709(13) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.44394(16) 0.23151(17) 0.44699(15) 0.0265(3) Uani 1 1 d . . . . .
O3 O 0.49284(15) 0.31006(14) -0.01512(13) 0.0183(3) Uani 1 1 d . . . . .
H3 H 0.415591 0.370045 -0.041769 0.027 Uiso 1 1 calc R U . . .
O5 O 0.78475(14) 0.49124(13) 0.03364(13) 0.0156(2) Uani 1 1 d . . . . .
O4 O 0.96379(14) 0.30132(14) 0.06823(14) 0.0180(3) Uani 1 1 d . . . . .
H4 H 1.035904 0.372524 0.033743 0.027 Uiso 1 1 calc R U . . .
C1 C 0.81122(19) 0.35529(19) 0.07692(17) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.67638(19) 0.23131(19) 0.15069(19) 0.0157(3) Uani 1 1 d . . . . .
H2A H 0.673084 0.178592 0.259270 0.019 Uiso 1 1 calc R U . . .
H2B H 0.708799 0.156898 0.109130 0.019 Uiso 1 1 calc R U . . .
C3 C 0.49936(19) 0.28249(18) 0.13222(18) 0.0140(3) Uani 1 1 d . . . . .
H3A H 0.478384 0.378376 0.143658 0.017 Uiso 1 1 calc R U . . .
C4 C 0.36763(18) 0.15959(17) 0.25234(17) 0.0125(3) Uani 1 1 d . . . . .
C5 C 0.3781(2) -0.00007(19) 0.2665(2) 0.0175(3) Uani 1 1 d . . . . .
H5A H 0.466527 -0.019755 0.191851 0.021 Uiso 1 1 calc R U . . .
H5B H 0.352988 -0.084613 0.368763 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2346(2) 0.09548(19) 0.21316(19) 0.0161(3) Uani 1 1 d . . . . .
H6A H 0.121173 0.069628 0.282620 0.019 Uiso 1 1 calc R U . . .
H6B H 0.234691 0.134474 0.105741 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1441(3) 0.3174(3) 0.3849(3) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
C8 C -0.0271(3) 0.2698(3) 0.4143(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
H8 H -0.057329 0.165303 0.456327 0.019 Uiso 0.797(3) 1 calc R U P A 1
C9 C -0.1471(3) 0.3761(2) 0.3815(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
H9 H -0.261559 0.344522 0.402314 0.019 Uiso 0.797(3) 1 calc R U P A 1
C10 C -0.1040(3) 0.5332(3) 0.3167(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
C11 C 0.0675(3) 0.5798(3) 0.2897(3) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
C12 C 0.1898(3) 0.4674(2) 0.3267(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
H12 H 0.304119 0.496272 0.310955 0.019 Uiso 0.797(3) 1 calc R U P A 1
C13 C 0.1099(3) 0.7363(2) 0.2256(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
H13 H 0.223200 0.768452 0.208692 0.019 Uiso 0.797(3) 1 calc R U P A 1
C14 C -0.0106(3) 0.8417(2) 0.1879(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
H14 H 0.019863 0.946423 0.143517 0.019 Uiso 0.797(3) 1 calc R U P A 1
C15 C -0.1799(3) 0.7958(3) 0.2145(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
H15 H -0.262479 0.870140 0.188037 0.019 Uiso 0.797(3) 1 calc R U P A 1
C16 C -0.2272(3) 0.6448(2) 0.2783(2) 0.0156(2) Uani 0.797(3) 1 d . . P A 1
H16 H -0.341909 0.615421 0.296545 0.019 Uiso 0.797(3) 1 calc R U P A 1
C7B C 0.1856(12) 0.3404(13) 0.3847(12) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
C8B C 0.2801(12) 0.4802(11) 0.3287(10) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
H8B H 0.398604 0.481860 0.320489 0.025 Uiso 0.203(3) 1 calc R U P A 2
C9B C 0.1929(11) 0.6098(11) 0.2881(9) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
H9B H 0.249852 0.704447 0.252604 0.025 Uiso 0.203(3) 1 calc R U P A 2
C10B C 0.0211(12) 0.6037(12) 0.2984(11) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
C11B C -0.0756(11) 0.7463(11) 0.2540(9) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
H11B H -0.019132 0.841457 0.217147 0.025 Uiso 0.203(3) 1 calc R U P A 2
C12B C -0.2406(12) 0.7383(12) 0.2668(10) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
H12B H -0.298632 0.829924 0.230271 0.025 Uiso 0.203(3) 1 calc R U P A 2
C13B C -0.3368(11) 0.5956(10) 0.3342(9) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
H13B H -0.456505 0.593559 0.349951 0.025 Uiso 0.203(3) 1 calc R U P A 2
C14B C -0.2500(11) 0.4642(11) 0.3743(10) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
H14B H -0.309257 0.369649 0.415316 0.025 Uiso 0.203(3) 1 calc R U P A 2
C15B C -0.0755(12) 0.4689(12) 0.3551(10) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
C16B C 0.0210(12) 0.3292(12) 0.3985(10) 0.0207(9) Uani 0.203(3) 1 d . . P A 2
H16B H -0.033954 0.233298 0.435688 0.025 Uiso 0.203(3) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4382(13) . ?
S1 O1 1.4419(12) . ?
S1 C7B 1.737(11) . ?
S1 C4 1.7739(16) . ?
S1 C7 1.786(3) . ?
O3 C3 1.422(2) . ?
O3 H3 0.8400 . ?
O5 C1 1.232(2) . ?
O4 C1 1.3140(18) . ?
O4 H4 0.8400 . ?
C1 C2 1.502(2) . ?
C2 C3 1.521(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.538(2) . ?
C3 H3A 1.0000 . ?
C4 C6 1.509(2) . ?
C4 C5 1.513(2) . ?
C5 C6 1.498(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.370(3) . ?
C7 C8 1.425(3) . ?
C8 C9 1.364(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.423(3) . ?
C9 H9 0.9500 . ?
C10 C16 1.420(3) . ?
C10 C11 1.429(3) . ?
C11 C13 1.417(3) . ?
C11 C12 1.419(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.367(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.410(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C7B C16B 1.323(13) . ?
C7B C8B 1.439(14) . ?
C8B C9B 1.359(13) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.383(13) . ?
C9B H9B 0.9500 . ?
C10B C15B 1.406(15) . ?
C10B C11B 1.499(13) . ?
C11B C12B 1.325(13) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.455(14) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.372(13) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.390(13) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.476(14) . ?
C16B H16B 0.9500 . ?

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 S1 O1 119.41(8) . . ?
O2 S1 C7B 97.2(3) . . ?
O1 S1 C7B 115.8(3) . . ?
O2 S1 C4 107.78(7) . . ?
O1 S1 C4 108.63(8) . . ?
C7B S1 C4 107.0(3) . . ?
O2 S1 C7 110.65(10) . . ?
O1 S1 C7 105.82(9) . . ?
C4 S1 C7 103.40(10) . . ?
C3 O3 H3 109.5 . . ?
C1 O4 H4 109.5 . . ?
O5 C1 O4 123.16(14) . . ?
O5 C1 C2 125.00(14) . . ?
O4 C1 C2 111.79(14) . . ?
C1 C2 C3 115.30(14) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
O3 C3 C2 107.28(13) . . ?
O3 C3 C4 111.57(13) . . ?
C2 C3 C4 109.77(13) . . ?
O3 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C6 C4 C5 59.42(11) . . ?
C6 C4 C3 122.35(14) . . ?
C5 C4 C3 120.13(13) . . ?
C6 C4 S1 114.96(11) . . ?
C5 C4 S1 116.24(11) . . ?
C3 C4 S1 113.50(11) . . ?
C6 C5 C4 60.16(10) . . ?
C6 C5 H5A 117.8 . . ?
C4 C5 H5A 117.8 . . ?
C6 C5 H5B 117.8 . . ?
C4 C5 H5B 117.8 . . ?
H5A C5 H5B 114.9 . . ?
C5 C6 C4 60.43(11) . . ?
C5 C6 H6A 117.7 . . ?
C4 C6 H6A 117.7 . . ?
C5 C6 H6B 117.7 . . ?
C4 C6 H6B 117.7 . . ?
H6A C6 H6B 114.8 . . ?
C12 C7 C8 121.3(2) . . ?
C12 C7 S1 120.06(17) . . ?
C8 C7 S1 118.68(18) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C16 C10 C9 121.65(19) . . ?
C16 C10 C11 119.2(2) . . ?
C9 C10 C11 119.1(2) . . ?
C13 C11 C12 122.3(2) . . ?
C13 C11 C10 119.0(2) . . ?
C12 C11 C10 118.7(2) . . ?
C7 C12 C11 120.4(2) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C11 120.69(19) . . ?
C14 C13 H13 119.7 . . ?
C11 C13 H13 119.7 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.0(2) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C10 119.80(19) . . ?
C15 C16 H16 120.1 . . ?
C10 C16 H16 120.1 . . ?
C16B C7B C8B 124.8(10) . . ?
C16B C7B S1 118.2(8) . . ?
C8B C7B S1 116.8(7) . . ?
C9B C8B C7B 117.2(9) . . ?
C9B C8B H8B 121.4 . . ?
C7B C8B H8B 121.4 . . ?
C8B C9B C10B 119.9(9) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B C15B 124.3(9) . . ?
C9B C10B C11B 120.1(9) . . ?
C15B C10B C11B 115.6(9) . . ?
C12B C11B C10B 119.4(9) . . ?
C12B C11B H11B 120.3 . . ?
C10B C11B H11B 120.3 . . ?
C11B C12B C13B 123.0(9) . . ?
C11B C12B H12B 118.5 . . ?
C13B C12B H12B 118.5 . . ?
C14B C13B C12B 118.1(8) . . ?
C14B C13B H13B 120.9 . . ?
C12B C13B H13B 120.9 . . ?
C13B C14B C15B 120.2(9) . . ?
C13B C14B H14B 119.9 . . ?
C15B C14B H14B 119.9 . . ?
C14B C15B C10B 123.5(10) . . ?
C14B C15B C16B 121.3(9) . . ?
C10B C15B C16B 115.2(9) . . ?
C7B C16B C15B 118.5(10) . . ?
C7B C16B H16B 120.7 . . ?
C15B C16B H16B 120.7 . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.072



