# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cd17409
_database_code_depnum_ccdc_archive 'CCDC 1562950'
_audit_update_record             
;
2017-07-18 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H27 N O S'
_chemical_formula_weight         317.47

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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'
'-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                   13.4779(14)
_cell_length_b                   8.1983(9)
_cell_length_c                   31.894(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3524.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4638
_cell_measurement_theta_min      5.109
_cell_measurement_theta_max      54.262

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18890
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.978
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3265
_reflns_number_gt                2738
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0643P)²+0.8899P] 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         3265
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001

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 1.00029(3) 0.19459(7) 0.66342(2) 0.04636(18) Uani 1 1 d . . . . .
N1 N 1.03740(11) 0.21477(17) 0.57766(4) 0.0346(3) Uani 1 1 d . . . . .
O1 O 1.16547(10) 0.00410(18) 0.53301(4) 0.0578(4) Uani 1 1 d . . . . .
C1 C 0.90342(12) 0.2738(2) 0.62777(5) 0.0347(4) Uani 1 1 d . . . . .
H1 H 0.8607 0.1824 0.6196 0.042 Uiso 1 1 calc R U . . .
C2 C 0.83885(13) 0.4026(2) 0.64874(5) 0.0406(4) Uani 1 1 d . . . . .
H2A H 0.7789 0.4155 0.6322 0.049 Uiso 1 1 calc R U . . .
H2B H 0.8192 0.3621 0.6761 0.049 Uiso 1 1 calc R U . . .
C3 C 0.88550(16) 0.5698(2) 0.65455(6) 0.0502(5) Uani 1 1 d . . . . .
H3A H 0.8487 0.6257 0.6764 0.060 Uiso 1 1 calc R U . . .
H3B H 0.9523 0.5535 0.6650 0.060 Uiso 1 1 calc R U . . .
C4 C 0.89202(15) 0.6828(2) 0.61767(6) 0.0498(5) Uani 1 1 d . . . . .
H4 H 0.9202 0.7838 0.6236 0.060 Uiso 1 1 calc R U . . .
C5 C 0.86463(15) 0.6634(2) 0.57830(6) 0.0465(5) Uani 1 1 d . . . . .
H5 H 0.8752 0.7524 0.5608 0.056 Uiso 1 1 calc R U . . .
C6 C 0.81866(14) 0.5162(2) 0.55818(6) 0.0438(4) Uani 1 1 d . . . . .
H6A H 0.7919 0.5477 0.5311 0.053 Uiso 1 1 calc R U . . .
H6B H 0.7637 0.4799 0.5754 0.053 Uiso 1 1 calc R U . . .
C7 C 0.89022(13) 0.3730(2) 0.55182(5) 0.0405(4) Uani 1 1 d . . . . .
H7A H 0.9310 0.3962 0.5275 0.049 Uiso 1 1 calc R U . . .
H7B H 0.8513 0.2767 0.5454 0.049 Uiso 1 1 calc R U . . .
C8 C 0.95939(13) 0.3319(2) 0.58861(5) 0.0332(4) Uani 1 1 d . . . . .
H8 H 0.9930 0.4336 0.5963 0.040 Uiso 1 1 calc R U . . .
C9 C 1.11391(14) 0.2786(2) 0.55028(6) 0.0466(5) Uani 1 1 d . . . . .
H9A H 1.1380 0.3817 0.5612 0.056 Uiso 1 1 calc R U . . .
H9B H 1.0866 0.2977 0.5226 0.056 Uiso 1 1 calc R U . . .
C10 C 1.19841(14) 0.1589(3) 0.54742(7) 0.0540(5) Uani 1 1 d . . . . .
H10A H 1.2483 0.2009 0.5284 0.065 Uiso 1 1 calc R U . . .
H10B H 1.2288 0.1467 0.5748 0.065 Uiso 1 1 calc R U . . .
C11 C 1.09064(16) -0.0566(3) 0.55994(7) 0.0577(6) Uani 1 1 d . . . . .
H11A H 1.1180 -0.0719 0.5878 0.069 Uiso 1 1 calc R U . . .
H11B H 1.0684 -0.1619 0.5498 0.069 Uiso 1 1 calc R U . . .
C12 C 1.00351(13) 0.0578(2) 0.56235(6) 0.0451(5) Uani 1 1 d . . . . .
H12A H 0.9740 0.0703 0.5348 0.054 Uiso 1 1 calc R U . . .
H12B H 0.9536 0.0138 0.5811 0.054 Uiso 1 1 calc R U . . .
C13 C 0.93369(13) 0.1717(2) 0.71111(5) 0.0405(4) Uani 1 1 d . . . . .
C14 C 0.86242(14) 0.0530(3) 0.71621(6) 0.0496(5) Uani 1 1 d . . . . .
H14 H 0.8460 -0.0144 0.6938 0.060 Uiso 1 1 calc R U . . .
C15 C 0.81518(15) 0.0331(3) 0.75423(7) 0.0589(6) Uani 1 1 d . . . . .
H15 H 0.7664 -0.0465 0.7569 0.071 Uiso 1 1 calc R U . . .
C16 C 0.83879(15) 0.1288(3) 0.78839(6) 0.0570(6) Uani 1 1 d . . . . .
C17 C 0.90999(17) 0.2472(3) 0.78299(6) 0.0599(6) Uani 1 1 d . . . . .
H17 H 0.9272 0.3134 0.8055 0.072 Uiso 1 1 calc R U . . .
C18 C 0.95625(16) 0.2696(3) 0.74489(6) 0.0529(5) Uani 1 1 d . . . . .
H18 H 1.0033 0.3518 0.7419 0.063 Uiso 1 1 calc R U . . .
C19 C 0.7901(2) 0.1011(4) 0.83056(7) 0.0934(10) Uani 1 1 d . . . . .
H19A H 0.8017 0.1939 0.8483 0.140 Uiso 1 1 calc R U . . .
H19B H 0.8178 0.0055 0.8434 0.140 Uiso 1 1 calc R U . . .
H19C H 0.7201 0.0864 0.8268 0.140 Uiso 1 1 calc R U . . .


_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 C13 1.7761(18) . ?
S1 C1 1.8489(16) . ?
N1 C9 1.449(2) . ?
N1 C12 1.450(2) . ?
N1 C8 1.466(2) . ?
O1 C11 1.415(2) . ?
O1 C10 1.421(3) . ?
C1 C2 1.524(2) . ?
C1 C8 1.535(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.500(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.319(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.501(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.533(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.536(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C9 C10 1.506(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.505(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.377(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 C19 1.513(3) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C13 S1 C1 101.94(8) . . ?
C9 N1 C12 109.97(14) . . ?
C9 N1 C8 114.66(14) . . ?
C12 N1 C8 115.82(14) . . ?
C11 O1 C10 109.90(15) . . ?
C2 C1 C8 114.99(14) . . ?
C2 C1 S1 112.13(12) . . ?
C8 C1 S1 105.21(11) . . ?
C2 C1 H1 108.1 . . ?
C8 C1 H1 108.1 . . ?
S1 C1 H1 108.1 . . ?
C3 C2 C1 116.28(15) . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C1 C2 H2B 108.2 . . ?
H2A C2 H2B 107.4 . . ?
C4 C3 C2 119.07(16) . . ?
C4 C3 H3A 107.5 . . ?
C2 C3 H3A 107.6 . . ?
C4 C3 H3B 107.5 . . ?
C2 C3 H3B 107.6 . . ?
H3A C3 H3B 107.0 . . ?
C5 C4 C3 131.01(18) . . ?
C5 C4 H4 114.5 . . ?
C3 C4 H4 114.5 . . ?
C4 C5 C6 128.30(18) . . ?
C4 C5 H5 115.8 . . ?
C6 C5 H5 115.8 . . ?
C5 C6 C7 114.38(15) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 116.66(14) . . ?
C6 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
C6 C7 H7B 108.1 . . ?
C8 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
N1 C8 C1 110.03(13) . . ?
N1 C8 C7 113.39(13) . . ?
C1 C8 C7 113.03(14) . . ?
N1 C8 H8 106.6 . . ?
C1 C8 H8 106.6 . . ?
C7 C8 H8 106.6 . . ?
N1 C9 C10 109.84(16) . . ?
N1 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O1 C10 C9 111.43(16) . . ?
O1 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
O1 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O1 C11 C12 111.59(17) . . ?
O1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C11 108.93(16) . . ?
N1 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
N1 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C18 C13 C14 118.25(17) . . ?
C18 C13 S1 119.79(15) . . ?
C14 C13 S1 121.89(15) . . ?
C13 C14 C15 120.63(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 117.59(18) . . ?
C17 C16 C19 121.3(2) . . ?
C15 C16 C19 121.1(2) . . ?
C16 C17 C18 121.3(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 120.8(2) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C13 S1 C1 C2 42.38(14) . . . . ?
C13 S1 C1 C8 168.06(12) . . . . ?
C8 C1 C2 C3 -45.3(2) . . . . ?
S1 C1 C2 C3 74.83(17) . . . . ?
C1 C2 C3 C4 77.9(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C5 C6 C7 -72.6(3) . . . . ?
C5 C6 C7 C8 43.9(2) . . . . ?
C9 N1 C8 C1 -161.42(14) . . . . ?
C12 N1 C8 C1 68.81(18) . . . . ?
C9 N1 C8 C7 70.9(2) . . . . ?
C12 N1 C8 C7 -58.88(19) . . . . ?
C2 C1 C8 N1 165.31(14) . . . . ?
S1 C1 C8 N1 41.43(16) . . . . ?
C2 C1 C8 C7 -66.80(19) . . . . ?
S1 C1 C8 C7 169.31(12) . . . . ?
C6 C7 C8 N1 -169.39(15) . . . . ?
C6 C7 C8 C1 64.5(2) . . . . ?
C12 N1 C9 C10 -57.4(2) . . . . ?
C8 N1 C9 C10 170.01(15) . . . . ?
C11 O1 C10 C9 -57.4(2) . . . . ?
N1 C9 C10 O1 57.2(2) . . . . ?
C10 O1 C11 C12 58.7(2) . . . . ?
C9 N1 C12 C11 57.9(2) . . . . ?
C8 N1 C12 C11 -170.06(15) . . . . ?
O1 C11 C12 N1 -59.1(2) . . . . ?
C1 S1 C13 C18 -112.85(16) . . . . ?
C1 S1 C13 C14 70.23(17) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
S1 C13 C14 C15 176.92(16) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C14 C15 C16 C19 -177.1(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C19 C16 C17 C18 178.2(2) . . . . ?
C14 C13 C18 C17 1.2(3) . . . . ?
S1 C13 C18 C17 -175.85(16) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

