# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 
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data_Edwin_JSO238_PHI
_database_code_depnum_ccdc_archive 'CCDC 1835571'
_audit_update_record             
;
2018-04-08 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H29 N O3 S'
_chemical_formula_sum            'C21 H29 N O3 S'
_chemical_formula_weight         375.51

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.906(3)
_cell_length_b                   20.872(5)
_cell_length_c                   10.617(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.655(3)
_cell_angle_gamma                90
_cell_volume                     2141.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5084
_cell_measurement_theta_min      2.195
_cell_measurement_theta_max      23.784

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   0.87
_exptl_transmission_factor_max   0.96
_exptl_crystal_size_max          0.889
_exptl_crystal_size_mid          0.655
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ANALYTICAL
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21336
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_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             4200
_reflns_number_gt                2836
_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 SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1055P)²+1.4110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4200
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2161
_refine_ls_wR_factor_gt          0.1846
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.01932(8) 0.06084(4) 0.82354(8) 0.0619(3) Uani 1 1 d . . . . .
O1 O 0.3862(2) 0.04394(11) 1.1254(2) 0.0679(6) Uani 1 1 d . . . . .
O2 O -0.0988(2) 0.03618(13) 0.8641(2) 0.0780(7) Uani 1 1 d . . . . .
N1 N 0.1376(3) 0.07037(15) 0.9532(3) 0.0624(7) Uani 1 1 d . . . . .
C2 C 0.7193(3) 0.22003(14) 1.0484(3) 0.0613(8) Uani 1 1 d . . . . .
O3 O 0.0089(3) 0.12013(11) 0.7541(2) 0.0781(7) Uani 1 1 d . . . . .
C12 C 0.0774(3) 0.00209(15) 0.7291(3) 0.0595(8) Uani 1 1 d . . . . .
C11 C 0.2670(3) 0.10110(18) 0.9449(3) 0.0684(9) Uani 1 1 d . . . . .
H11A H 0.248529 0.143575 0.908055 0.082 Uiso 1 1 calc R U . . .
H11B H 0.312528 0.076331 0.888956 0.082 Uiso 1 1 calc R U . . .
C5 C 0.4883(3) 0.14431(15) 1.0715(3) 0.0613(8) Uani 1 1 d . . . . .
C6 C 0.5930(3) 0.11970(15) 1.0193(3) 0.0697(9) Uani 1 1 d . . . . .
H6 H 0.587977 0.077321 0.991627 0.084 Uiso 1 1 calc R U . . .
C8 C 0.3598(3) 0.10599(16) 1.0774(3) 0.0655(8) Uani 1 1 d . . . . .
H8 H 0.309404 0.128905 1.133289 0.079 Uiso 1 1 calc R U . . .
C13 C 0.1415(3) 0.01894(18) 0.6308(4) 0.0739(9) Uani 1 1 d . . . . .
H13 H 0.150990 0.061976 0.611723 0.089 Uiso 1 1 calc R U . . .
C4 C 0.5022(4) 0.20671(16) 1.1135(4) 0.0779(10) Uani 1 1 d . . . . .
H4 H 0.433938 0.224708 1.150140 0.093 Uiso 1 1 calc R U . . .
C14 C 0.1909(4) -0.0271(2) 0.5611(4) 0.0821(10) Uani 1 1 d . . . . .
H14 H 0.232681 -0.014828 0.494516 0.099 Uiso 1 1 calc R U . . .
C15 C 0.1804(4) -0.0911(2) 0.5873(3) 0.0779(10) Uani 1 1 d . . . . .
C7 C 0.7055(3) 0.15658(16) 1.0072(3) 0.0690(9) Uani 1 1 d . . . . .
H7 H 0.773711 0.138521 0.970510 0.083 Uiso 1 1 calc R U . . .
C3 C 0.6149(4) 0.24323(16) 1.1026(4) 0.0800(11) Uani 1 1 d . . . . .
H3 H 0.620635 0.285151 1.133059 0.096 Uiso 1 1 calc R U . . .
C10 C 0.4521(4) -0.0277(2) 1.3006(4) 0.0900(12) Uani 1 1 d . . . . .
H10A H 0.369859 -0.051837 1.265908 0.135 Uiso 1 1 calc R U . . .
H10B H 0.472747 -0.030508 1.393099 0.135 Uiso 1 1 calc R U . . .
H10C H 0.528008 -0.044877 1.268481 0.135 Uiso 1 1 calc R U . . .
C1 C 0.8412(4) 0.26187(17) 1.0352(4) 0.0807(10) Uani 1 1 d . . . . .
C9 C 0.4304(5) 0.0395(2) 1.2614(4) 0.0916(12) Uani 1 1 d . . . . .
H9A H 0.361227 0.058352 1.302041 0.110 Uiso 1 1 calc R U . . .
H9B H 0.516017 0.063161 1.289594 0.110 Uiso 1 1 calc R U . . .
C17 C 0.0612(5) -0.06139(19) 0.7540(4) 0.0947(13) Uani 1 1 d . . . . .
H17 H 0.016321 -0.073558 0.818546 0.114 Uiso 1 1 calc R U . . .
C18 C 0.2390(5) -0.1419(3) 0.5150(5) 0.1112(16) Uani 1 1 d . . . . .
H18A H 0.331019 -0.152359 0.560858 0.167 Uiso 1 1 calc R U . . .
H18B H 0.241691 -0.126306 0.430504 0.167 Uiso 1 1 calc R U . . .
H18C H 0.181845 -0.179413 0.507343 0.167 Uiso 1 1 calc R U . . .
C16 C 0.1116(6) -0.1073(2) 0.6829(4) 0.1031(14) Uani 1 1 d . . . . .
H16 H 0.099028 -0.150377 0.699673 0.124 Uiso 1 1 calc R U . . .
C21 C 0.9654(6) 0.2237(3) 1.0250(10) 0.202(4) Uani 1 1 d . . . . .
H21A H 0.948121 0.201713 0.943632 0.303 Uiso 1 1 calc R U . . .
H21B H 0.984787 0.192941 1.093920 0.303 Uiso 1 1 calc R U . . .
H21C H 1.043300 0.251748 1.031050 0.303 Uiso 1 1 calc R U . . .
C20 C 0.8914(8) 0.3011(4) 1.1557(9) 0.212(4) Uani 1 1 d . . . . .
H20A H 0.975248 0.322884 1.150142 0.319 Uiso 1 1 calc R U . . .
H20B H 0.908750 0.273400 1.229681 0.319 Uiso 1 1 calc R U . . .
H20C H 0.822118 0.332031 1.164049 0.319 Uiso 1 1 calc R U . . .
C19 C 0.7998(9) 0.3046(5) 0.9271(11) 0.303(8) Uani 1 1 d . . . . .
H19A H 0.820781 0.285417 0.851426 0.455 Uiso 1 1 calc R U . . .
H19B H 0.849002 0.344332 0.945104 0.455 Uiso 1 1 calc R U . . .
H19C H 0.702180 0.312442 0.912745 0.455 Uiso 1 1 calc R U . . .
H1 H 0.152(4) 0.036(2) 0.991(4) 0.097(14) Uiso 1 1 d . . . . .


_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 1.428(2) . ?
S1 O3 1.432(2) . ?
S1 N1 1.613(3) . ?
S1 C12 1.759(3) . ?
O1 C8 1.395(4) . ?
O1 C9 1.417(4) . ?
N1 C11 1.453(4) . ?
N1 H1 0.83(4) . ?
C2 C3 1.378(5) . ?
C2 C7 1.392(4) . ?
C2 C1 1.521(5) . ?
C12 C17 1.367(5) . ?
C12 C13 1.381(5) . ?
C11 C8 1.506(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 C4 1.374(4) . ?
C5 C6 1.378(4) . ?
C5 C8 1.516(4) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C13 C14 1.368(5) . ?
C13 H13 0.9300 . ?
C4 C3 1.377(5) . ?
C4 H4 0.9300 . ?
C14 C15 1.373(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(6) . ?
C15 C18 1.498(5) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C10 C9 1.466(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C1 C19 1.439(8) . ?
C1 C21 1.490(7) . ?
C1 C20 1.509(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17 C16 1.380(6) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C16 H16 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
O2 S1 O3 119.65(15) . . ?
O2 S1 N1 106.09(15) . . ?
O3 S1 N1 106.84(16) . . ?
O2 S1 C12 108.21(16) . . ?
O3 S1 C12 107.76(15) . . ?
N1 S1 C12 107.79(15) . . ?
C8 O1 C9 115.1(3) . . ?
C11 N1 S1 119.2(2) . . ?
C11 N1 H1 111(3) . . ?
S1 N1 H1 109(3) . . ?
C3 C2 C7 115.8(3) . . ?
C3 C2 C1 121.4(3) . . ?
C7 C2 C1 122.8(3) . . ?
C17 C12 C13 119.1(3) . . ?
C17 C12 S1 119.9(3) . . ?
C13 C12 S1 121.0(3) . . ?
N1 C11 C8 109.8(3) . . ?
N1 C11 H11A 109.7 . . ?
C8 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
C8 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C4 C5 C6 116.9(3) . . ?
C4 C5 C8 120.8(3) . . ?
C6 C5 C8 122.2(3) . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
O1 C8 C11 107.8(3) . . ?
O1 C8 C5 114.4(3) . . ?
C11 C8 C5 110.1(3) . . ?
O1 C8 H8 108.1 . . ?
C11 C8 H8 108.1 . . ?
C5 C8 H8 108.1 . . ?
C14 C13 C12 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 117.3(4) . . ?
C14 C15 C18 121.9(4) . . ?
C16 C15 C18 120.8(4) . . ?
C6 C7 C2 121.7(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C2 C3 C4 122.5(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C19 C1 C21 111.7(7) . . ?
C19 C1 C20 108.9(7) . . ?
C21 C1 C20 103.2(6) . . ?
C19 C1 C2 109.7(4) . . ?
C21 C1 C2 112.6(3) . . ?
C20 C1 C2 110.7(4) . . ?
O1 C9 C10 110.2(3) . . ?
O1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
O1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C12 C17 C16 119.7(4) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C16 C15 121.8(4) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C1 C21 H21A 109.5 . . ?
C1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C20 H20A 109.5 . . ?
C1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 C19 H19A 109.5 . . ?
C1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.483
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.046

