# Electronic Supplementary Material (ESI) for ChemComm.
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 1505786'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 N O3 S'
_chemical_formula_sum            'C20 H23 N O3 S'
_chemical_formula_weight         357.45
_chemical_absolute_configuration syn

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           orthorhombic
_symmetry_space_group_name_H-M   P212121
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.3041(12)
_cell_length_b                   10.2744(15)
_cell_length_c                   22.465(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1916.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2423
_cell_measurement_theta_min      2.1797
_cell_measurement_theta_max      21.0825

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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-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            9795
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3388
_reflns_number_gt                2797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0547P)²+0.0000P] 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(8)
_refine_ls_number_reflns         3388
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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 0.71098(8) 0.83000(6) 0.12262(3) 0.04884(18) Uani 1 1 d . . .
O1 O 0.41489(19) 0.66192(15) 0.10598(7) 0.0500(4) Uani 1 1 d . . .
O2 O 0.72640(19) 0.52896(16) 0.02294(7) 0.0509(4) Uani 1 1 d . . .
O3 O 0.6888(3) 0.95402(17) 0.09106(9) 0.0745(6) Uani 1 1 d . . .
N1 N 0.7653(2) 0.7218(2) 0.06894(8) 0.0472(5) Uani 1 1 d . . .
C1 C 0.1812(3) 0.4545(3) 0.12735(11) 0.0590(7) Uani 1 1 d . . .
H1A H 0.2025 0.5147 0.1573 0.071 Uiso 1 1 calc R . .
C2 C 0.0663(4) 0.3594(3) 0.13625(12) 0.0757(9) Uani 1 1 d . . .
H2A H 0.0088 0.3575 0.1718 0.091 Uiso 1 1 calc R . .
C3 C 0.0361(4) 0.2679(3) 0.09356(13) 0.0692(8) Uani 1 1 d . . .
H3A H -0.0408 0.2036 0.1000 0.083 Uiso 1 1 calc R . .
C4 C 0.1198(4) 0.2719(3) 0.04160(12) 0.0675(8) Uani 1 1 d . . .
H4A H 0.1015 0.2087 0.0127 0.081 Uiso 1 1 calc R . .
C5 C 0.2313(3) 0.3683(3) 0.03116(11) 0.0592(7) Uani 1 1 d . . .
H5A H 0.2851 0.3716 -0.0051 0.071 Uiso 1 1 calc R . .
C6 C 0.2637(3) 0.4608(2) 0.07477(9) 0.0426(6) Uani 1 1 d . . .
C7 C 0.3864(3) 0.5611(2) 0.06243(10) 0.0456(6) Uani 1 1 d . . .
H7A H 0.3930 0.5894 0.0208 0.055 Uiso 1 1 calc R . .
C8 C 0.5394(3) 0.5684(2) 0.09612(9) 0.0406(5) Uani 1 1 d . . .
C9 C 0.5739(3) 0.4768(2) 0.14623(10) 0.0441(6) Uani 1 1 d . . .
C10 C 0.5766(3) 0.5216(3) 0.20387(11) 0.0645(8) Uani 1 1 d . . .
H10A H 0.5572 0.6092 0.2114 0.077 Uiso 1 1 calc R . .
C11 C 0.6079(4) 0.4380(5) 0.25083(14) 0.0933(11) Uani 1 1 d U . .
H11A H 0.6103 0.4697 0.2896 0.112 Uiso 1 1 calc R . .
C12 C 0.6347(4) 0.3113(5) 0.2403(2) 0.1064(14) Uani 1 1 d U . .
H12A H 0.6556 0.2553 0.2719 0.128 Uiso 1 1 calc R . .
C13 C 0.6315(4) 0.2642(4) 0.1833(2) 0.0965(12) Uani 1 1 d . . .
H13A H 0.6502 0.1762 0.1762 0.116 Uiso 1 1 calc R . .
C14 C 0.6005(3) 0.3471(3) 0.13604(13) 0.0677(8) Uani 1 1 d . . .
H14A H 0.5978 0.3147 0.0974 0.081 Uiso 1 1 calc R . .
C15 C 0.6851(3) 0.6178(2) 0.06330(10) 0.0404(5) Uani 1 1 d . . .
C16 C 0.8726(3) 0.5522(3) -0.01123(11) 0.0620(8) Uani 1 1 d . . .
H16A H 0.8889 0.4818 -0.0387 0.093 Uiso 1 1 calc R . .
H16B H 0.9629 0.5577 0.0153 0.093 Uiso 1 1 calc R . .
H16C H 0.8623 0.6323 -0.0329 0.093 Uiso 1 1 calc R . .
C17 C 0.9094(3) 0.8395(2) 0.15835(10) 0.0487(6) Uani 1 1 d . . .
C18 C 1.0416(3) 0.8647(3) 0.11312(13) 0.0710(8) Uani 1 1 d . . .
H18A H 1.1436 0.8695 0.1331 0.106 Uiso 1 1 calc R . .
H18B H 1.0209 0.9454 0.0930 0.106 Uiso 1 1 calc R . .
H18C H 1.0438 0.7951 0.0846 0.106 Uiso 1 1 calc R . .
C19 C 0.9326(4) 0.7140(3) 0.19243(14) 0.0718(8) Uani 1 1 d . . .
H19A H 1.0354 0.7153 0.2120 0.108 Uiso 1 1 calc R . .
H19B H 0.9285 0.6418 0.1653 0.108 Uiso 1 1 calc R . .
H19C H 0.8488 0.7051 0.2216 0.108 Uiso 1 1 calc R . .
C20 C 0.8953(4) 0.9535(3) 0.20118(12) 0.0670(8) Uani 1 1 d . . .
H20A H 0.9955 0.9649 0.2219 0.100 Uiso 1 1 calc R . .
H20B H 0.8112 0.9364 0.2294 0.100 Uiso 1 1 calc R . .
H20C H 0.8704 1.0312 0.1793 0.100 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 O3 1.4698(19) . ?
S1 N1 1.701(2) . ?
S1 C17 1.836(2) . ?
O1 C8 1.429(3) . ?
O1 C7 1.444(3) . ?
O2 C15 1.332(3) . ?
O2 C16 1.456(3) . ?
N1 C15 1.265(3) . ?
C1 C6 1.367(3) . ?
C1 C2 1.380(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.366(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.359(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.476(3) . ?
C7 C8 1.481(3) . ?
C7 H7A 0.9800 . ?
C8 C9 1.495(3) . ?
C8 C15 1.505(3) . ?
C9 C14 1.370(4) . ?
C9 C10 1.374(3) . ?
C10 C11 1.385(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.342(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.371(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.512(3) . ?
C17 C18 1.518(4) . ?
C17 C20 1.520(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
O3 S1 N1 104.95(11) . . ?
O3 S1 C17 106.11(12) . . ?
N1 S1 C17 96.14(10) . . ?
C8 O1 C7 62.04(14) . . ?
C15 O2 C16 117.5(2) . . ?
C15 N1 S1 118.91(17) . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 H1A 119.8 . . ?
C2 C1 H1A 119.8 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 122.8(2) . . ?
C5 C6 C7 118.6(2) . . ?
O1 C7 C6 119.12(18) . . ?
O1 C7 C8 58.48(13) . . ?
C6 C7 C8 122.10(19) . . ?
O1 C7 H7A 115.1 . . ?
C6 C7 H7A 115.1 . . ?
C8 C7 H7A 115.1 . . ?
O1 C8 C7 59.48(14) . . ?
O1 C8 C9 116.43(17) . . ?
C7 C8 C9 121.15(19) . . ?
O1 C8 C15 115.50(18) . . ?
C7 C8 C15 117.14(18) . . ?
C9 C8 C15 115.32(18) . . ?
C14 C9 C10 118.7(2) . . ?
C14 C9 C8 121.2(2) . . ?
C10 C9 C8 120.1(2) . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C9 C14 C13 120.0(3) . . ?
C9 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
N1 C15 O2 120.8(2) . . ?
N1 C15 C8 131.2(2) . . ?
O2 C15 C8 108.00(19) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C17 C18 113.1(2) . . ?
C19 C17 C20 110.3(2) . . ?
C18 C17 C20 110.4(2) . . ?
C19 C17 S1 106.88(18) . . ?
C18 C17 S1 111.43(16) . . ?
C20 C17 S1 104.40(18) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O3 S1 N1 C15 -125.65(19) . . . . ?
C17 S1 N1 C15 125.83(19) . . . . ?
C6 C1 C2 C3 1.8(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C1 C6 C7 179.3(3) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C8 O1 C7 C6 111.8(2) . . . . ?
C1 C6 C7 O1 -3.7(3) . . . . ?
C5 C6 C7 O1 176.62(19) . . . . ?
C1 C6 C7 C8 65.4(3) . . . . ?
C5 C6 C7 C8 -114.3(2) . . . . ?
C7 O1 C8 C9 -112.2(2) . . . . ?
C7 O1 C8 C15 107.8(2) . . . . ?
C6 C7 C8 O1 -106.8(2) . . . . ?
O1 C7 C8 C9 104.3(2) . . . . ?
C6 C7 C8 C9 -2.5(3) . . . . ?
O1 C7 C8 C15 -105.0(2) . . . . ?
C6 C7 C8 C15 148.2(2) . . . . ?
O1 C8 C9 C14 137.7(2) . . . . ?
C7 C8 C9 C14 68.9(3) . . . . ?
C15 C8 C9 C14 -82.2(3) . . . . ?
O1 C8 C9 C10 -41.2(3) . . . . ?
C7 C8 C9 C10 -110.0(3) . . . . ?
C15 C8 C9 C10 98.9(3) . . . . ?
C14 C9 C10 C11 0.9(4) . . . . ?
C8 C9 C10 C11 179.8(2) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C10 C9 C14 C13 -0.8(4) . . . . ?
C8 C9 C14 C13 -179.7(2) . . . . ?
C12 C13 C14 C9 0.4(5) . . . . ?
S1 N1 C15 O2 -178.12(15) . . . . ?
S1 N1 C15 C8 1.4(3) . . . . ?
C16 O2 C15 N1 4.1(3) . . . . ?
C16 O2 C15 C8 -175.49(18) . . . . ?
O1 C8 C15 N1 44.2(3) . . . . ?
C7 C8 C15 N1 111.4(3) . . . . ?
C9 C8 C15 N1 -96.2(3) . . . . ?
O1 C8 C15 O2 -136.23(19) . . . . ?
C7 C8 C15 O2 -69.0(2) . . . . ?
C9 C8 C15 O2 83.3(2) . . . . ?
O3 S1 C17 C19 178.55(19) . . . . ?
N1 S1 C17 C19 -73.92(19) . . . . ?
O3 S1 C17 C18 -57.4(2) . . . . ?
N1 S1 C17 C18 50.1(2) . . . . ?
O3 S1 C17 C20 61.69(19) . . . . ?
N1 S1 C17 C20 169.22(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.032

