# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1556719'
_audit_update_record             
;
2017-07-18 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 N O S'
_chemical_formula_sum            'C25 H23 N O S'
_chemical_formula_weight         385.50

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'


loop_
_symmetry_equiv_pos_as_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                   10.190(2)
_cell_length_b                   15.310(3)
_cell_length_c                   13.623(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.81(3)
_cell_angle_gamma                90.00
_cell_volume                     2105.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    39454
_cell_measurement_theta_min      3.012
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      289(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            39454
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4818
_reflns_number_gt                3027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    'SHELXTL and Diamond'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_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)+(0.0541P)²+0.9318P] 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_number_reflns         4818
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1394
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
S1 S 0.50205(6) 0.15309(4) 0.30158(4) 0.05020(19) Uani 1 1 d . . .
N1 N 0.2583(2) 0.27253(13) 0.51518(14) 0.0556(5) Uani 1 1 d . . .
H1 H 0.2717 0.2613 0.4555 0.067 Uiso 1 1 calc R . .
O1 O 0.1939(2) 0.37831(13) 0.61144(15) 0.0855(7) Uani 1 1 d . . .
C1 C 0.6275(2) 0.16796(15) 0.39955(17) 0.0475(5) Uani 1 1 d . . .
C2 C 0.7605(2) 0.18496(19) 0.3938(2) 0.0652(7) Uani 1 1 d . . .
H2 H 0.7908 0.1912 0.3328 0.078 Uiso 1 1 calc R . .
C3 C 0.8458(3) 0.1923(2) 0.4809(2) 0.0746(8) Uani 1 1 d . . .
H3 H 0.9350 0.2035 0.4785 0.090 Uiso 1 1 calc R . .
C4 C 0.8012(3) 0.1831(2) 0.5723(2) 0.0689(8) Uani 1 1 d . . .
H4 H 0.8609 0.1878 0.6301 0.083 Uiso 1 1 calc R . .
C5 C 0.6694(2) 0.16730(16) 0.57817(18) 0.0546(6) Uani 1 1 d . . .
H5 H 0.6399 0.1623 0.6396 0.066 Uiso 1 1 calc R . .
C6 C 0.5806(2) 0.15875(14) 0.49125(16) 0.0431(5) Uani 1 1 d . . .
C7 C 0.4403(2) 0.14086(13) 0.48003(15) 0.0389(5) Uani 1 1 d . . .
C8 C 0.3863(2) 0.13457(13) 0.38301(15) 0.0408(5) Uani 1 1 d . . .
C9 C 0.2483(2) 0.11469(14) 0.34104(15) 0.0426(5) Uani 1 1 d . . .
C10 C 0.1741(2) 0.05433(17) 0.38571(17) 0.0550(6) Uani 1 1 d . . .
H10 H 0.2118 0.0258 0.4429 0.066 Uiso 1 1 calc R . .
C11 C 0.0454(3) 0.0361(2) 0.3466(2) 0.0675(7) Uani 1 1 d . . .
H11 H -0.0031 -0.0046 0.3774 0.081 Uiso 1 1 calc R . .
C12 C -0.0119(3) 0.0779(2) 0.2622(2) 0.0673(7) Uani 1 1 d . . .
H12 H -0.0990 0.0657 0.2361 0.081 Uiso 1 1 calc R . .
C13 C 0.0595(3) 0.13734(19) 0.2169(2) 0.0673(7) Uani 1 1 d . . .
H13 H 0.0207 0.1659 0.1600 0.081 Uiso 1 1 calc R . .
C14 C 0.1897(2) 0.15536(17) 0.25540(18) 0.0558(6) Uani 1 1 d . . .
H14 H 0.2381 0.1952 0.2234 0.067 Uiso 1 1 calc R . .
C15 C 0.3637(2) 0.13568(14) 0.56556(15) 0.0400(5) Uani 1 1 d . . .
C16 C 0.3821(2) 0.06672(15) 0.63170(16) 0.0488(6) Uani 1 1 d . . .
H16 H 0.4433 0.0235 0.6224 0.059 Uiso 1 1 calc R . .
C17 C 0.3116(2) 0.06071(17) 0.71131(17) 0.0556(6) Uani 1 1 d . . .
H17 H 0.3254 0.0141 0.7553 0.067 Uiso 1 1 calc R . .
C18 C 0.2210(3) 0.12436(18) 0.72444(17) 0.0578(7) Uani 1 1 d . . .
H18 H 0.1727 0.1204 0.7775 0.069 Uiso 1 1 calc R . .
C19 C 0.2004(2) 0.19418(17) 0.66019(17) 0.0540(6) Uani 1 1 d . . .
H19 H 0.1379 0.2365 0.6697 0.065 Uiso 1 1 calc R . .
C20 C 0.2730(2) 0.20147(14) 0.58110(15) 0.0426(5) Uani 1 1 d . . .
C21 C 0.2260(2) 0.35568(16) 0.53284(17) 0.0486(5) Uani 1 1 d . . .
C22 C 0.2341(3) 0.41992(17) 0.44799(19) 0.0621(7) Uani 1 1 d . . .
C23 C 0.3476(5) 0.4008(3) 0.3908(3) 0.1290(17) Uani 1 1 d . . .
H23A H 0.4297 0.4046 0.4345 0.193 Uiso 1 1 calc R . .
H23B H 0.3476 0.4425 0.3383 0.193 Uiso 1 1 calc R . .
H23C H 0.3378 0.3430 0.3634 0.193 Uiso 1 1 calc R . .
C24 C 0.1073(5) 0.4108(4) 0.3758(3) 0.151(2) Uani 1 1 d . . .
H24A H 0.1005 0.3523 0.3503 0.227 Uiso 1 1 calc R . .
H24B H 0.1089 0.4512 0.3220 0.227 Uiso 1 1 calc R . .
H24C H 0.0325 0.4232 0.4094 0.227 Uiso 1 1 calc R . .
C25 C 0.2459(5) 0.5114(2) 0.4892(3) 0.1344(18) Uani 1 1 d . . .
H25A H 0.1758 0.5218 0.5283 0.202 Uiso 1 1 calc R . .
H25B H 0.2396 0.5526 0.4357 0.202 Uiso 1 1 calc R . .
H25C H 0.3299 0.5180 0.5300 0.202 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 C1 1.733(2) . ?
S1 C8 1.748(2) . ?
N1 C21 1.345(3) . ?
N1 C20 1.406(3) . ?
N1 H1 0.8600 . ?
O1 C21 1.212(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(3) . ?
C7 C8 1.364(3) . ?
C7 C15 1.490(3) . ?
C8 C9 1.476(3) . ?
C9 C14 1.384(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.384(3) . ?
C15 C20 1.402(3) . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(3) . ?
C19 H19 0.9300 . ?
C21 C22 1.528(3) . ?
C22 C25 1.507(5) . ?
C22 C23 1.508(4) . ?
C22 C24 1.520(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C1 S1 C8 91.32(10) . . ?
C21 N1 C20 128.75(19) . . ?
C21 N1 H1 115.6 . . ?
C20 N1 H1 115.6 . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 S1 127.1(2) . . ?
C6 C1 S1 111.58(16) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.5(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 128.8(2) . . ?
C1 C6 C7 112.1(2) . . ?
C8 C7 C6 112.30(18) . . ?
C8 C7 C15 124.65(19) . . ?
C6 C7 C15 122.95(19) . . ?
C7 C8 C9 128.86(19) . . ?
C7 C8 S1 112.65(16) . . ?
C9 C8 S1 118.49(15) . . ?
C14 C9 C10 118.1(2) . . ?
C14 C9 C8 120.9(2) . . ?
C10 C9 C8 121.0(2) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.7(2) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C20 118.91(19) . . ?
C16 C15 C7 120.69(19) . . ?
C20 C15 C7 120.39(19) . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 119.3(2) . . ?
C19 C20 N1 122.3(2) . . ?
C15 C20 N1 118.35(18) . . ?
O1 C21 N1 122.0(2) . . ?
O1 C21 C22 122.2(2) . . ?
N1 C21 C22 115.7(2) . . ?
C25 C22 C23 110.2(3) . . ?
C25 C22 C24 110.1(3) . . ?
C23 C22 C24 107.0(3) . . ?
C25 C22 C21 109.0(2) . . ?
C23 C22 C21 112.9(2) . . ?
C24 C22 C21 107.6(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.043
