# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_16AU09_0m
_database_code_depnum_ccdc_archive 'CCDC 1522351'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 N O2 S'
_chemical_formula_weight         355.48

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   11.8441(4)
_cell_length_b                   11.9103(5)
_cell_length_c                   13.4579(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1898.46(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.25

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9469
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_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 KAPPA APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25711
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         28.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             25711
_reflns_number_gt                20461
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 _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 APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 2008)'

_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)+(0.0350P)²+0.2445P]
 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       none
_refine_ls_abs_structure_details 
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.48(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         25711
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_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 0.98155(6) 1.38768(8) 1.10496(6) 0.0556(3) Uani 1 1 d . . . . .
N1 N 1.01840(18) 1.3532(2) 1.21631(16) 0.0472(7) Uani 1 1 d . . . . .
O1 O 0.86815(15) 1.4285(2) 1.10955(17) 0.0710(7) Uani 1 1 d . . . . .
O2 O 1.06971(17) 1.4576(2) 1.06630(15) 0.0701(7) Uani 1 1 d . . . . .
C1 C 0.7347(3) 1.2841(3) 1.3015(3) 0.0686(10) Uani 1 1 d . . . . .
H1 H 0.7313 1.2140 1.2712 0.082 Uiso 1 1 calc R U . . .
C2 C 0.6362(3) 1.3348(4) 1.3352(3) 0.0790(12) Uani 1 1 d . . . . .
H2 H 0.5673 1.2983 1.3275 0.095 Uiso 1 1 calc R U . . .
C3 C 0.6398(3) 1.4369(4) 1.3791(3) 0.0765(11) Uani 1 1 d . . . . .
H3 H 0.5737 1.4706 1.4014 0.092 Uiso 1 1 calc R U . . .
C4 C 0.7415(3) 1.4902(3) 1.3905(3) 0.0756(11) Uani 1 1 d . . . . .
H4 H 0.7444 1.5605 1.4206 0.091 Uiso 1 1 calc R U . . .
C5 C 0.8392(3) 1.4400(3) 1.3577(2) 0.0647(10) Uani 1 1 d . . . . .
H5 H 0.9077 1.4768 1.3663 0.078 Uiso 1 1 calc R U . . .
C6 C 0.8376(2) 1.3371(3) 1.3127(2) 0.0500(9) Uani 1 1 d . . . . .
C7 C 0.9431(2) 1.2795(3) 1.2776(2) 0.0502(8) Uani 1 1 d . . . . .
H7 H 0.9215 1.2143 1.2375 0.060 Uiso 1 1 calc R U . . .
C8 C 1.0238(2) 1.2403(3) 1.3594(2) 0.0601(9) Uani 1 1 d . . . . .
H8A H 1.0306 1.2962 1.4114 0.072 Uiso 1 1 calc R U . . .
H8B H 0.9988 1.1700 1.3884 0.072 Uiso 1 1 calc R U . . .
C9 C 1.1397(2) 1.3309(3) 1.2390(2) 0.0500(9) Uani 1 1 d . . . . .
H9 H 1.1808 1.3148 1.1775 0.060 Uiso 1 1 calc R U . . .
C10 C 1.1347(2) 1.2257(3) 1.3036(2) 0.0584(9) Uani 1 1 d . . . . .
H10 H 1.1259 1.1612 1.2590 0.070 Uiso 1 1 calc R U . . .
C11 C 0.9782(2) 1.2646(3) 1.0337(2) 0.0516(9) Uani 1 1 d . . . . .
C12 C 1.0731(3) 1.2285(4) 0.9836(2) 0.0704(11) Uani 1 1 d . . . . .
H12 H 1.1389 1.2709 0.9856 0.084 Uiso 1 1 calc R U . . .
C13 C 1.0704(3) 1.1297(4) 0.9308(3) 0.0742(11) Uani 1 1 d . . . . .
H13 H 1.1353 1.1057 0.8983 0.089 Uiso 1 1 calc R U . . .
C14 C 0.9740(3) 1.0655(3) 0.9248(2) 0.0630(9) Uani 1 1 d . . . . .
C15 C 0.8792(3) 1.1037(4) 0.9747(2) 0.0676(11) Uani 1 1 d . . . . .
H15 H 0.8127 1.0623 0.9714 0.081 Uiso 1 1 calc R U . . .
C16 C 0.8813(2) 1.2007(4) 1.0288(2) 0.0633(10) Uani 1 1 d . . . . .
H16 H 0.8168 1.2238 1.0625 0.076 Uiso 1 1 calc R U . . .
C17 C 0.9729(3) 0.9572(3) 0.8688(3) 0.0947(13) Uani 1 1 d . . . . .
H17A H 1.0454 0.9451 0.8389 0.142 Uiso 1 1 calc R U . . .
H17B H 0.9161 0.9602 0.8180 0.142 Uiso 1 1 calc R U . . .
H17C H 0.9564 0.8967 0.9137 0.142 Uiso 1 1 calc R U . . .
C18 C 1.2416(3) 1.2060(4) 1.3649(3) 0.0836(13) Uani 1 1 d . . . . .
H18A H 1.2258 1.1499 1.4152 0.100 Uiso 1 1 calc R U . . .
H18B H 1.3000 1.1763 1.3218 0.100 Uiso 1 1 calc R U . . .
C19 C 1.2852(3) 1.3095(4) 1.4145(3) 0.0925(15) Uani 1 1 d . . . . .
H19A H 1.3562 1.2928 1.4472 0.111 Uiso 1 1 calc R U . . .
H19B H 1.2318 1.3338 1.4648 0.111 Uiso 1 1 calc R U . . .
C21 C 1.1904(2) 1.4315(3) 1.2899(3) 0.0667(10) Uani 1 1 d . . . . .
H21A H 1.1381 1.4593 1.3396 0.080 Uiso 1 1 calc R U . . .
H21B H 1.2022 1.4906 1.2414 0.080 Uiso 1 1 calc R U . . .
C20 C 1.3026(3) 1.4031(4) 1.3395(3) 0.0886(14) Uani 1 1 d . . . . .
H20A H 1.3569 1.3796 1.2897 0.106 Uiso 1 1 calc R U . . .
H20B H 1.3322 1.4691 1.3728 0.106 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 O1 1.4298(19) . ?
S1 O2 1.433(2) . ?
S1 N1 1.614(2) . ?
S1 C11 1.752(3) . ?
N1 C9 1.492(3) . ?
N1 C7 1.498(4) . ?
C1 C6 1.380(4) . ?
C1 C2 1.390(4) . ?
C2 C3 1.352(5) . ?
C3 C4 1.370(5) . ?
C4 C5 1.376(4) . ?
C5 C6 1.368(5) . ?
C6 C7 1.502(4) . ?
C7 C8 1.531(4) . ?
C8 C10 1.524(4) . ?
C9 C21 1.506(4) . ?
C9 C10 1.526(4) . ?
C10 C18 1.529(4) . ?
C11 C12 1.379(4) . ?
C11 C16 1.380(4) . ?
C12 C13 1.375(5) . ?
C13 C14 1.376(5) . ?
C14 C15 1.385(4) . ?
C14 C17 1.494(5) . ?
C15 C16 1.365(5) . ?
C18 C19 1.494(6) . ?
C19 C20 1.518(5) . ?
C21 C20 1.525(4) . ?

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
O1 S1 O2 120.16(15) . . ?
O1 S1 N1 107.49(13) . . ?
O2 S1 N1 106.73(13) . . ?
O1 S1 C11 106.68(14) . . ?
O2 S1 C11 107.69(15) . . ?
N1 S1 C11 107.53(13) . . ?
C9 N1 C7 110.9(2) . . ?
C9 N1 S1 119.72(18) . . ?
C7 N1 S1 119.93(19) . . ?
C6 C1 C2 120.5(4) . . ?
C3 C2 C1 120.4(4) . . ?
C2 C3 C4 119.6(4) . . ?
C3 C4 C5 120.1(4) . . ?
C6 C5 C4 121.3(3) . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 C7 122.4(3) . . ?
C1 C6 C7 119.5(3) . . ?
N1 C7 C6 113.7(3) . . ?
N1 C7 C8 101.7(2) . . ?
C6 C7 C8 115.6(2) . . ?
C10 C8 C7 102.6(2) . . ?
N1 C9 C21 109.6(3) . . ?
N1 C9 C10 103.1(2) . . ?
C21 C9 C10 114.2(3) . . ?
C8 C10 C9 102.7(3) . . ?
C8 C10 C18 117.7(3) . . ?
C9 C10 C18 113.7(3) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 S1 120.7(3) . . ?
C16 C11 S1 120.5(3) . . ?
C13 C12 C11 120.1(3) . . ?
C12 C13 C14 121.7(3) . . ?
C13 C14 C15 117.5(3) . . ?
C13 C14 C17 121.1(3) . . ?
C15 C14 C17 121.4(4) . . ?
C16 C15 C14 121.4(3) . . ?
C15 C16 C11 120.5(3) . . ?
C19 C18 C10 113.6(3) . . ?
C18 C19 C20 110.8(3) . . ?
C9 C21 C20 111.8(3) . . ?
C19 C20 C21 109.6(3) . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-2

