# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1429502'
_audit_update_record             
;
2015-10-05 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N O3 S'
_chemical_formula_weight         393.48

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'
N N 0.0061 0.0033 '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   'C 1 c 1'

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

_cell_length_a                   7.2967(5)
_cell_length_b                   18.0150(13)
_cell_length_c                   15.0313(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.477(2)
_cell_angle_gamma                90.00
_cell_volume                     1959.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3540
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.3

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8329
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         28.31
_reflns_number_total             3540
_reflns_number_gt                3403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0427P)²+0.6509P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_number_reflns         3540
_refine_ls_number_parameters     256
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
S1A S 0.84348(5) 0.14158(2) 0.59366(3) 0.01666(9) Uani 1 1 d . . .
C6A C 0.4366(2) 0.40047(9) 0.80577(12) 0.0170(3) Uani 1 1 d . . .
H6A H 0.4819 0.3530 0.7980 0.020 Uiso 1 1 calc R . .
O3A O 0.75986(18) 0.34223(6) 0.51815(9) 0.0210(3) Uani 1 1 d . . .
O1A O 0.18490(16) 0.25546(7) 0.35693(9) 0.0202(3) Uani 1 1 d . . .
O2A O 0.46251(16) 0.20241(6) 0.35013(8) 0.0177(2) Uani 1 1 d . . .
C7A C 0.2793(2) 0.39997(8) 0.64663(11) 0.0147(3) Uani 1 1 d . . .
H7A H 0.1728 0.4158 0.6109 0.018 Uiso 1 1 calc R . .
N1A N 0.59230(18) 0.23471(7) 0.52115(9) 0.0129(3) Uani 1 1 d . . .
C2A C 0.2468(2) 0.50385(8) 0.75033(12) 0.0154(3) Uani 1 1 d . . .
H2A H 0.1630 0.5256 0.7060 0.018 Uiso 1 1 calc R . .
C4A C 0.4173(3) 0.50802(10) 0.89861(13) 0.0214(4) Uani 1 1 d . . .
H4A H 0.4532 0.5333 0.9520 0.026 Uiso 1 1 calc R . .
C5A C 0.4841(2) 0.43649(9) 0.88619(12) 0.0190(3) Uani 1 1 d . . .
H5A H 0.5606 0.4133 0.9323 0.023 Uiso 1 1 calc R . .
C1A C 0.3207(2) 0.43418(8) 0.73527(11) 0.0137(3) Uani 1 1 d . . .
C8A C 0.3817(2) 0.34745(8) 0.61204(11) 0.0145(3) Uani 1 1 d . . .
H8A H 0.4889 0.3303 0.6460 0.017 Uiso 1 1 calc R . .
C9A C 0.3284(2) 0.31747(8) 0.52374(11) 0.0144(3) Uani 1 1 d . . .
H9A H 0.2203 0.3359 0.4918 0.017 Uiso 1 1 calc R . .
C10A C 0.4200(2) 0.26510(8) 0.48265(11) 0.0129(3) Uani 1 1 d . . .
C13A C 0.6138(2) 0.15340(8) 0.53007(11) 0.0120(3) Uani 1 1 d . . .
H13A H 0.6103 0.1307 0.4706 0.014 Uiso 1 1 calc R . .
C16A C 0.4710(2) 0.11739(8) 0.58062(11) 0.0125(3) Uani 1 1 d . . .
C17A C 0.4250(2) 0.15055(8) 0.65843(11) 0.0141(3) Uani 1 1 d . . .
H17A H 0.4765 0.1963 0.6760 0.017 Uiso 1 1 calc R . .
C18A C 0.3042(2) 0.11718(9) 0.71065(12) 0.0155(3) Uani 1 1 d . . .
C22A C 0.2554(3) 0.15456(10) 0.79396(13) 0.0233(4) Uani 1 1 d . . .
H22A H 0.3486 0.1438 0.8434 0.035 Uiso 1 1 calc R . .
H22B H 0.1381 0.1365 0.8071 0.035 Uiso 1 1 calc R . .
H22C H 0.2484 0.2072 0.7845 0.035 Uiso 1 1 calc R . .
C15A C 0.7529(2) 0.27529(9) 0.52741(11) 0.0147(3) Uani 1 1 d . . .
C14A C 0.9215(2) 0.22585(9) 0.54561(12) 0.0176(3) Uani 1 1 d . . .
H14A H 1.0164 0.2497 0.5872 0.021 Uiso 1 1 calc R . .
H14B H 0.9719 0.2152 0.4904 0.021 Uiso 1 1 calc R . .
C19A C 0.2320(2) 0.04780(9) 0.68354(12) 0.0165(3) Uani 1 1 d . . .
H19A H 0.1529 0.0238 0.7179 0.020 Uiso 1 1 calc R . .
C20A C 0.2766(2) 0.01411(9) 0.60609(12) 0.0157(3) Uani 1 1 d . . .
H20A H 0.2260 -0.0320 0.5894 0.019 Uiso 1 1 calc R . .
C21A C 0.3960(2) 0.04793(8) 0.55245(11) 0.0136(3) Uani 1 1 d . . .
C23A C 0.4433(3) 0.00938(9) 0.46952(12) 0.0186(3) Uani 1 1 d . . .
H23A H 0.4033 0.0393 0.4178 0.028 Uiso 1 1 calc R . .
H23B H 0.3822 -0.0379 0.4635 0.028 Uiso 1 1 calc R . .
H23C H 0.5746 0.0022 0.4744 0.028 Uiso 1 1 calc R . .
C11A C 0.3404(2) 0.24136(8) 0.39111(11) 0.0141(3) Uani 1 1 d . . .
C12A C 0.3977(3) 0.17845(11) 0.25949(12) 0.0236(4) Uani 1 1 d . . .
H12A H 0.3394 0.2193 0.2260 0.035 Uiso 1 1 calc R . .
H12B H 0.3102 0.1389 0.2612 0.035 Uiso 1 1 calc R . .
H12C H 0.5006 0.1613 0.2313 0.035 Uiso 1 1 calc R . .
C3A C 0.2970(2) 0.54115(9) 0.83082(12) 0.0191(3) Uani 1 1 d . . .
H3A H 0.2500 0.5883 0.8393 0.023 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
S1A C14A 1.8049(17) . ?
S1A C13A 1.8303(16) . ?
C6A C5A 1.376(2) . ?
C6A C1A 1.405(2) . ?
C6A H6A 0.9300 . ?
O3A C15A 1.2156(19) . ?
O1A C11A 1.210(2) . ?
O2A C11A 1.3446(19) . ?
O2A C12A 1.449(2) . ?
C7A C8A 1.351(2) . ?
C7A C1A 1.463(2) . ?
C7A H7A 0.9300 . ?
N1A C15A 1.374(2) . ?
N1A C10A 1.423(2) . ?
N1A C13A 1.4774(18) . ?
C2A C3A 1.391(2) . ?
C2A C1A 1.396(2) . ?
C2A H2A 0.9300 . ?
C4A C3A 1.390(3) . ?
C4A C5A 1.399(2) . ?
C4A H4A 0.9300 . ?
C5A H5A 0.9300 . ?
C8A C9A 1.439(2) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.351(2) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.485(2) . ?
C13A C16A 1.513(2) . ?
C13A H13A 0.9800 . ?
C16A C17A 1.393(2) . ?
C16A C21A 1.409(2) . ?
C17A C18A 1.391(2) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.396(2) . ?
C18A C22A 1.505(2) . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C15A C14A 1.515(2) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C19A C20A 1.389(2) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.401(2) . ?
C20A H20A 0.9300 . ?
C21A C23A 1.506(2) . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C3A H3A 0.9300 . ?

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
C14A S1A C13A 90.48(7) . . ?
C5A C6A C1A 121.12(15) . . ?
C5A C6A H6A 119.4 . . ?
C1A C6A H6A 119.4 . . ?
C11A O2A C12A 115.58(13) . . ?
C8A C7A C1A 125.88(16) . . ?
C8A C7A H7A 117.1 . . ?
C1A C7A H7A 117.1 . . ?
C15A N1A C10A 121.57(13) . . ?
C15A N1A C13A 116.20(13) . . ?
C10A N1A C13A 119.75(13) . . ?
C3A C2A C1A 120.80(16) . . ?
C3A C2A H2A 119.6 . . ?
C1A C2A H2A 119.6 . . ?
C3A C4A C5A 119.71(17) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C6A C5A C4A 119.96(17) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C2A C1A C6A 118.27(15) . . ?
C2A C1A C7A 119.19(15) . . ?
C6A C1A C7A 122.52(14) . . ?
C7A C8A C9A 121.43(15) . . ?
C7A C8A H8A 119.3 . . ?
C9A C8A H8A 119.3 . . ?
C10A C9A C8A 126.41(16) . . ?
C10A C9A H9A 116.8 . . ?
C8A C9A H9A 116.8 . . ?
C9A C10A N1A 123.09(15) . . ?
C9A C10A C11A 117.89(15) . . ?
N1A C10A C11A 118.95(13) . . ?
N1A C13A C16A 113.49(12) . . ?
N1A C13A S1A 104.01(10) . . ?
C16A C13A S1A 109.35(11) . . ?
N1A C13A H13A 109.9 . . ?
C16A C13A H13A 109.9 . . ?
S1A C13A H13A 109.9 . . ?
C17A C16A C21A 120.43(14) . . ?
C17A C16A C13A 119.66(13) . . ?
C21A C16A C13A 119.74(13) . . ?
C18A C17A C16A 121.89(15) . . ?
C18A C17A H17A 119.1 . . ?
C16A C17A H17A 119.1 . . ?
C17A C18A C19A 117.70(15) . . ?
C17A C18A C22A 120.81(15) . . ?
C19A C18A C22A 121.48(15) . . ?
C18A C22A H22A 109.5 . . ?
C18A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C18A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
O3A C15A N1A 124.59(16) . . ?
O3A C15A C14A 123.99(15) . . ?
N1A C15A C14A 111.41(13) . . ?
C15A C14A S1A 106.00(10) . . ?
C15A C14A H14A 110.5 . . ?
S1A C14A H14A 110.5 . . ?
C15A C14A H14B 110.5 . . ?
S1A C14A H14B 110.5 . . ?
H14A C14A H14B 108.7 . . ?
C20A C19A C18A 121.02(15) . . ?
C20A C19A H19A 119.5 . . ?
C18A C19A H19A 119.5 . . ?
C19A C20A C21A 121.56(14) . . ?
C19A C20A H20A 119.2 . . ?
C21A C20A H20A 119.2 . . ?
C20A C21A C16A 117.38(14) . . ?
C20A C21A C23A 120.17(13) . . ?
C16A C21A C23A 122.44(14) . . ?
C21A C23A H23A 109.5 . . ?
C21A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C21A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
O1A C11A O2A 123.75(15) . . ?
O1A C11A C10A 124.38(14) . . ?
O2A C11A C10A 111.87(14) . . ?
O2A C12A H12A 109.5 . . ?
O2A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
O2A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C4A C3A C2A 119.98(15) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?

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
C1A C6A C5A C4A -0.2(2) . . . . ?
C3A C4A C5A C6A 2.6(3) . . . . ?
C3A C2A C1A C6A 4.5(2) . . . . ?
C3A C2A C1A C7A -173.92(15) . . . . ?
C5A C6A C1A C2A -3.3(2) . . . . ?
C5A C6A C1A C7A 175.06(14) . . . . ?
C8A C7A C1A C2A 156.94(16) . . . . ?
C8A C7A C1A C6A -21.4(2) . . . . ?
C1A C7A C8A C9A -179.91(14) . . . . ?
C7A C8A C9A C10A 179.95(15) . . . . ?
C8A C9A C10A N1A -3.5(2) . . . . ?
C8A C9A C10A C11A 179.62(14) . . . . ?
C15A N1A C10A C9A -72.01(19) . . . . ?
C13A N1A C10A C9A 126.53(16) . . . . ?
C15A N1A C10A C11A 104.79(17) . . . . ?
C13A N1A C10A C11A -56.68(18) . . . . ?
C15A N1A C13A C16A 142.70(14) . . . . ?
C10A N1A C13A C16A -54.87(18) . . . . ?
C15A N1A C13A S1A 23.96(15) . . . . ?
C10A N1A C13A S1A -173.61(11) . . . . ?
C14A S1A C13A N1A -30.40(10) . . . . ?
C14A S1A C13A C16A -151.93(11) . . . . ?
N1A C13A C16A C17A -43.2(2) . . . . ?
S1A C13A C16A C17A 72.39(16) . . . . ?
N1A C13A C16A C21A 141.47(15) . . . . ?
S1A C13A C16A C21A -102.91(15) . . . . ?
C21A C16A C17A C18A -0.3(2) . . . . ?
C13A C16A C17A C18A -175.53(14) . . . . ?
C16A C17A C18A C19A 1.2(2) . . . . ?
C16A C17A C18A C22A -179.42(16) . . . . ?
C10A N1A C15A O3A 14.9(2) . . . . ?
C13A N1A C15A O3A 177.03(15) . . . . ?
C10A N1A C15A C14A -163.94(13) . . . . ?
C13A N1A C15A C14A -1.86(18) . . . . ?
O3A C15A C14A S1A 159.40(14) . . . . ?
N1A C15A C14A S1A -21.71(16) . . . . ?
C13A S1A C14A C15A 30.06(12) . . . . ?
C17A C18A C19A C20A -1.3(2) . . . . ?
C22A C18A C19A C20A 179.38(16) . . . . ?
C18A C19A C20A C21A 0.3(3) . . . . ?
C19A C20A C21A C16A 0.7(2) . . . . ?
C19A C20A C21A C23A 179.20(16) . . . . ?
C17A C16A C21A C20A -0.7(2) . . . . ?
C13A C16A C21A C20A 174.57(14) . . . . ?
C17A C16A C21A C23A -179.21(15) . . . . ?
C13A C16A C21A C23A -3.9(2) . . . . ?
C12A O2A C11A O1A 1.1(2) . . . . ?
C12A O2A C11A C10A -178.62(13) . . . . ?
C9A C10A C11A O1A -13.6(2) . . . . ?
N1A C10A C11A O1A 169.41(15) . . . . ?
C9A C10A C11A O2A 166.07(13) . . . . ?
N1A C10A C11A O2A -10.89(18) . . . . ?
C5A C4A C3A C2A -1.4(3) . . . . ?
C1A C2A C3A C4A -2.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
