# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_b150114a_0ma_a_a_a
_database_code_depnum_ccdc_archive 'CCDC 1043637'
_audit_update_record             
;
2015-01-15 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2015-01-15
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H15 N O S'
_chemical_formula_sum            'C14 H15 N O S'
_chemical_formula_weight         245.33
_chemical_melting_point          ?
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   17.5010(19)
_cell_length_b                   5.6716(6)
_cell_length_c                   12.6807(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.641(3)
_cell_angle_gamma                90.00
_cell_volume                     1217.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8403
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      3.23
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_exptl_special_details           sadabs
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19390
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2001
_reflns_number_total             2486
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2486
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1504
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.66585(3) 0.67870(10) 0.56221(4) 0.0294(2) Uani 1 1 d . . .
O1 O 0.76587(9) 1.0537(2) 0.52787(11) 0.0311(4) Uani 1 1 d . . .
N1 N 0.70945(9) 0.6175(3) 0.81490(13) 0.0234(4) Uani 1 1 d . . .
H1 H 0.7219 0.6001 0.8845 0.028 Uiso 1 1 calc R . .
C1 C 0.62796(11) 0.4737(3) 0.64064(16) 0.0209(4) Uani 1 1 d . . .
C2 C 0.57177(12) 0.3136(4) 0.58626(18) 0.0268(5) Uani 1 1 d . . .
H2 H 0.5540 0.3215 0.5108 0.032 Uiso 1 1 calc R . .
C3 C 0.54170(12) 0.1427(4) 0.64221(19) 0.0306(5) Uani 1 1 d . . .
H3 H 0.5043 0.0362 0.6043 0.037 Uiso 1 1 calc R . .
C4 C 0.56704(12) 0.1301(4) 0.75404(19) 0.0292(5) Uani 1 1 d . . .
H4 H 0.5471 0.0148 0.7919 0.035 Uiso 1 1 calc R . .
C5 C 0.62240(11) 0.2901(4) 0.80981(17) 0.0247(5) Uani 1 1 d . . .
H5 H 0.6394 0.2822 0.8854 0.030 Uiso 1 1 calc R . .
C6 C 0.65282(11) 0.4620(3) 0.75421(16) 0.0197(4) Uani 1 1 d . . .
C7 C 0.74608(11) 0.7909(3) 0.77481(16) 0.0194(4) Uani 1 1 d . . .
C8 C 0.73298(11) 0.8379(3) 0.66616(16) 0.0203(4) Uani 1 1 d . . .
C9 C 0.77528(11) 1.0186(3) 0.62684(16) 0.0208(4) Uani 1 1 d . . .
C10 C 0.83154(12) 1.1714(3) 0.70850(17) 0.0242(5) Uani 1 1 d . . .
H10A H 0.8031 1.3081 0.7245 0.029 Uiso 1 1 calc R . .
H10B H 0.8728 1.2272 0.6760 0.029 Uiso 1 1 calc R . .
C11 C 0.86983(11) 1.0451(3) 0.81535(16) 0.0210(4) Uani 1 1 d . . .
C12 C 0.80381(11) 0.9326(3) 0.85829(16) 0.0224(5) Uani 1 1 d . . .
H12A H 0.8275 0.8310 0.9194 0.027 Uiso 1 1 calc R . .
H12B H 0.7754 1.0563 0.8851 0.027 Uiso 1 1 calc R . .
C13 C 0.92689(12) 0.8575(4) 0.79545(19) 0.0311(5) Uani 1 1 d . . .
H13A H 0.8993 0.7501 0.7403 0.047 Uiso 1 1 calc R . .
H13B H 0.9484 0.7726 0.8618 0.047 Uiso 1 1 calc R . .
H13C H 0.9690 0.9315 0.7717 0.047 Uiso 1 1 calc R . .
C14 C 0.91432(13) 1.2202(4) 0.90020(18) 0.0301(5) Uani 1 1 d . . .
H14A H 0.9549 1.2954 0.8737 0.045 Uiso 1 1 calc R . .
H14B H 0.9378 1.1381 0.9667 0.045 Uiso 1 1 calc R . .
H14C H 0.8782 1.3371 0.9136 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0385(4) 0.0347(4) 0.0145(3) -0.0012(2) 0.0055(2) -0.0126(2)
O1 0.0437(9) 0.0336(8) 0.0175(8) 0.0018(6) 0.0105(7) -0.0069(7)
N1 0.0270(9) 0.0304(9) 0.0128(9) -0.0001(7) 0.0048(7) -0.0059(7)
C1 0.0190(10) 0.0242(10) 0.0210(11) -0.0008(8) 0.0080(8) 0.0025(8)
C2 0.0249(11) 0.0344(12) 0.0221(11) -0.0053(9) 0.0080(9) -0.0014(9)
C3 0.0280(11) 0.0324(12) 0.0338(13) -0.0110(10) 0.0123(10) -0.0073(9)
C4 0.0293(11) 0.0278(11) 0.0356(13) 0.0018(10) 0.0173(10) -0.0044(9)
C5 0.0239(10) 0.0309(11) 0.0219(11) 0.0004(9) 0.0102(9) 0.0003(8)
C6 0.0192(10) 0.0223(10) 0.0195(10) -0.0026(8) 0.0086(8) 0.0004(8)
C7 0.0208(10) 0.0212(10) 0.0182(10) -0.0001(8) 0.0085(8) 0.0030(8)
C8 0.0200(10) 0.0229(10) 0.0178(11) -0.0018(8) 0.0043(8) 0.0001(8)
C9 0.0230(10) 0.0219(10) 0.0183(11) 0.0004(8) 0.0070(8) 0.0030(8)
C10 0.0270(11) 0.0215(10) 0.0247(12) -0.0003(8) 0.0078(9) -0.0021(8)
C11 0.0221(10) 0.0217(10) 0.0191(10) -0.0012(8) 0.0051(8) -0.0002(8)
C12 0.0235(10) 0.0256(10) 0.0186(10) 0.0000(8) 0.0062(8) 0.0002(8)
C13 0.0246(11) 0.0315(12) 0.0375(14) -0.0016(10) 0.0084(10) 0.0032(9)
C14 0.0289(11) 0.0297(11) 0.0301(13) -0.0031(9) 0.0048(9) -0.0062(9)

_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 1.7648(19) . ?
S1 C8 1.775(2) . ?
O1 C9 1.240(2) . ?
N1 H1 0.8600 . ?
N1 C6 1.402(2) . ?
N1 C7 1.342(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.397(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C7 C8 1.365(3) . ?
C7 C12 1.499(3) . ?
C8 C9 1.426(3) . ?
C9 C10 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.529(3) . ?
C11 C12 1.535(3) . ?
C11 C13 1.523(3) . ?
C11 C14 1.525(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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 100.91(9) . . ?
C6 N1 H1 116.9 . . ?
C7 N1 H1 116.9 . . ?
C7 N1 C6 126.29(17) . . ?
C2 C1 S1 118.11(15) . . ?
C2 C1 C6 118.59(18) . . ?
C6 C1 S1 123.29(15) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.60(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 N1 121.92(17) . . ?
C5 C6 N1 118.17(18) . . ?
C5 C6 C1 119.90(18) . . ?
N1 C7 C8 123.44(18) . . ?
N1 C7 C12 115.25(17) . . ?
C8 C7 C12 121.31(17) . . ?
C7 C8 S1 124.13(15) . . ?
C7 C8 C9 121.59(17) . . ?
C9 C8 S1 114.25(15) . . ?
O1 C9 C8 121.44(18) . . ?
O1 C9 C10 119.93(17) . . ?
C8 C9 C10 118.62(17) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C9 C10 C11 113.75(16) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 C12 107.97(16) . . ?
C13 C11 C10 109.82(17) . . ?
C13 C11 C12 110.60(16) . . ?
C13 C11 C14 109.41(16) . . ?
C14 C11 C10 110.58(15) . . ?
C14 C11 C12 108.44(16) . . ?
C7 C12 C11 113.94(16) . . ?
C7 C12 H12A 108.8 . . ?
C7 C12 H12B 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.99 2.804(2) 158.2 4_576

