# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1859584'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O2 S'
_chemical_formula_weight         323.40

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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

loop_
_symmetry_equiv_pos_as_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                   5.5128(6)
_cell_length_b                   14.1945(18)
_cell_length_c                   20.649(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1615.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    961
_cell_measurement_theta_min      2.4394
_cell_measurement_theta_max      17.7025

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12082
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_sigmaI/netI    0.1468
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.52
_reflns_number_total             3680
_reflns_number_gt                1611
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0585P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.95(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3680
_refine_ls_number_parameters     208
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1734
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.958
_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 0.6326(2) 0.24649(10) 0.17580(7) 0.0670(4) Uani 1 1 d U . .
C6 C 0.5009(9) 0.4634(3) 0.1825(2) 0.0513(11) Uani 1 1 d U . .
O2 O 0.8433(7) 0.0979(2) 0.13473(17) 0.0692(10) Uani 1 1 d U . .
N1 N 0.5172(7) 0.1353(2) 0.07268(17) 0.0467(9) Uani 1 1 d U . .
C14 C 0.5262(8) -0.0389(3) 0.0542(2) 0.0421(11) Uani 1 1 d U . .
O1 O 0.1931(7) 0.1673(2) 0.00855(18) 0.0712(11) Uani 1 1 d U . .
C7 C 0.2958(9) 0.3905(3) 0.1847(2) 0.0583(13) Uani 1 1 d U . .
H7A H 0.1562 0.4176 0.1619 0.070 Uiso 1 1 calc R . .
C15 C 0.6718(9) -0.1141(3) 0.0393(2) 0.0577(13) Uani 1 1 d U . .
H15A H 0.8111 -0.1038 0.0149 0.069 Uiso 1 1 calc R . .
C12 C 0.6723(9) 0.1492(3) 0.1238(2) 0.0495(12) Uani 1 1 d U . .
C19 C 0.3144(9) -0.0571(3) 0.0892(2) 0.0556(13) Uani 1 1 d U . .
H19A H 0.2064 -0.0086 0.0985 0.067 Uiso 1 1 calc R . .
C16 C 0.6192(10) -0.2041(3) 0.0592(3) 0.0655(15) Uani 1 1 d U . .
H16A H 0.7223 -0.2535 0.0483 0.079 Uiso 1 1 calc R . .
C11 C 0.3101(9) 0.1889(3) 0.0564(3) 0.0500(12) Uani 1 1 d U . .
C9 C 0.3726(9) 0.3006(3) 0.1475(2) 0.0493(11) Uani 1 1 d U . .
C17 C 0.4138(10) -0.2212(3) 0.0952(3) 0.0632(14) Uani 1 1 d U . .
H17A H 0.3768 -0.2818 0.1092 0.076 Uiso 1 1 calc R . .
C5 C 0.5923(10) 0.5058(3) 0.2366(3) 0.0685(15) Uani 1 1 d U . .
H5A H 0.5339 0.4896 0.2773 0.082 Uiso 1 1 calc R . .
C10 C 0.2468(8) 0.2689(3) 0.0964(2) 0.0458(11) Uani 1 1 d U . .
H10A H 0.1057 0.3012 0.0857 0.055 Uiso 1 1 calc R . .
C13 C 0.5883(9) 0.0577(3) 0.0284(2) 0.0536(12) Uani 1 1 d U . .
H13A H 0.7617 0.0610 0.0208 0.064 Uiso 1 1 calc R . .
H13B H 0.5074 0.0665 -0.0129 0.064 Uiso 1 1 calc R . .
C1 C 0.5903(11) 0.4895(3) 0.1226(3) 0.0646(15) Uani 1 1 d U . .
H1A H 0.5277 0.4611 0.0856 0.078 Uiso 1 1 calc R . .
C18 C 0.2670(10) -0.1478(4) 0.1099(3) 0.0617(14) Uani 1 1 d U . .
H18A H 0.1292 -0.1589 0.1347 0.074 Uiso 1 1 calc R . .
C2 C 0.7682(11) 0.5557(4) 0.1163(3) 0.0740(17) Uani 1 1 d U . .
H2A H 0.8260 0.5719 0.0755 0.089 Uiso 1 1 calc R . .
C8 C 0.2122(11) 0.3643(4) 0.2525(3) 0.0771(17) Uani 1 1 d U . .
H8A H 0.1620 0.4201 0.2750 0.116 Uiso 1 1 calc R . .
H8B H 0.3435 0.3351 0.2755 0.116 Uiso 1 1 calc R . .
H8C H 0.0785 0.3212 0.2497 0.116 Uiso 1 1 calc R . .
C3 C 0.8621(11) 0.5985(4) 0.1709(3) 0.0807(16) Uani 1 1 d U . .
H3A H 0.9835 0.6436 0.1671 0.097 Uiso 1 1 calc R . .
C4 C 0.7763(11) 0.5744(4) 0.2302(3) 0.0821(17) Uani 1 1 d U . .
H4A H 0.8391 0.6033 0.2670 0.099 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 0.0617(8) 0.0617(8) 0.0777(9) -0.0190(8) -0.0161(7) 0.0061(7)
C6 0.071(3) 0.033(3) 0.050(3) -0.006(2) 0.006(3) 0.003(2)
O2 0.069(2) 0.057(2) 0.082(3) 0.0003(18) -0.015(2) 0.019(2)
N1 0.054(2) 0.036(2) 0.050(2) -0.0073(17) -0.0027(19) 0.0011(18)
C14 0.044(3) 0.038(2) 0.045(3) -0.006(2) -0.002(2) -0.004(2)
O1 0.071(2) 0.069(3) 0.073(3) -0.0047(19) -0.021(2) 0.001(2)
C7 0.063(3) 0.050(3) 0.062(3) -0.006(3) 0.000(3) 0.004(2)
C15 0.053(3) 0.051(3) 0.069(3) -0.003(3) 0.011(3) 0.005(2)
C12 0.049(3) 0.044(3) 0.056(3) -0.002(2) 0.002(2) 0.003(2)
C19 0.053(3) 0.049(3) 0.065(3) -0.001(3) 0.006(2) 0.008(2)
C16 0.063(3) 0.037(3) 0.096(4) 0.002(3) 0.015(3) 0.005(3)
C11 0.052(3) 0.037(3) 0.061(3) 0.003(2) -0.007(3) -0.004(2)
C9 0.046(3) 0.038(2) 0.064(3) -0.004(2) 0.010(2) 0.002(2)
C17 0.072(4) 0.046(3) 0.072(4) 0.004(3) -0.002(3) -0.003(3)
C5 0.093(4) 0.057(3) 0.055(3) -0.007(3) 0.006(3) -0.011(3)
C10 0.045(3) 0.032(3) 0.060(3) 0.002(2) -0.003(2) 0.001(2)
C13 0.075(3) 0.039(3) 0.047(3) -0.006(2) 0.011(2) 0.007(2)
C1 0.096(4) 0.043(3) 0.054(3) 0.001(2) 0.006(3) 0.003(3)
C18 0.057(3) 0.056(3) 0.073(4) -0.001(3) 0.015(3) -0.004(3)
C2 0.099(4) 0.041(3) 0.082(4) 0.004(3) 0.033(3) 0.008(3)
C8 0.088(4) 0.071(4) 0.072(4) -0.016(3) 0.028(3) -0.007(3)
C3 0.086(4) 0.044(3) 0.112(5) 0.000(3) 0.013(4) -0.006(3)
C4 0.099(4) 0.066(4) 0.081(4) -0.007(3) -0.012(4) -0.019(3)

_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 C9 1.728(5) . ?
S1 C12 1.762(5) . ?
C6 C5 1.365(7) . ?
C6 C1 1.382(7) . ?
C6 C7 1.534(6) . ?
O2 C12 1.212(5) . ?
N1 C12 1.373(6) . ?
N1 C11 1.412(6) . ?
N1 C13 1.485(5) . ?
C14 C15 1.371(6) . ?
C14 C19 1.397(6) . ?
C14 C13 1.510(6) . ?
O1 C11 1.219(5) . ?
C7 C8 1.520(7) . ?
C7 C9 1.548(6) . ?
C15 C16 1.373(7) . ?
C19 C18 1.382(7) . ?
C16 C17 1.376(7) . ?
C11 C10 1.446(6) . ?
C9 C10 1.340(6) . ?
C17 C18 1.353(7) . ?
C5 C4 1.412(7) . ?
C1 C2 1.364(7) . ?
C2 C3 1.382(8) . ?
C3 C4 1.356(8) . ?

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
C9 S1 C12 104.2(2) . . ?
C5 C6 C1 118.9(5) . . ?
C5 C6 C7 123.1(5) . . ?
C1 C6 C7 118.0(4) . . ?
C12 N1 C11 127.5(4) . . ?
C12 N1 C13 114.6(4) . . ?
C11 N1 C13 117.8(4) . . ?
C15 C14 C19 117.5(4) . . ?
C15 C14 C13 119.7(4) . . ?
C19 C14 C13 122.7(4) . . ?
C8 C7 C6 114.6(4) . . ?
C8 C7 C9 109.8(4) . . ?
C6 C7 C9 109.9(4) . . ?
C14 C15 C16 122.3(5) . . ?
O2 C12 N1 122.7(4) . . ?
O2 C12 S1 117.0(4) . . ?
N1 C12 S1 120.2(4) . . ?
C18 C19 C14 119.4(4) . . ?
C15 C16 C17 119.9(5) . . ?
O1 C11 N1 119.0(4) . . ?
O1 C11 C10 122.2(4) . . ?
N1 C11 C10 118.8(4) . . ?
C10 C9 C7 121.8(4) . . ?
C10 C9 S1 123.1(4) . . ?
C7 C9 S1 115.2(4) . . ?
C18 C17 C16 118.5(5) . . ?
C6 C5 C4 119.6(5) . . ?
C9 C10 C11 126.1(4) . . ?
N1 C13 C14 113.4(4) . . ?
C2 C1 C6 121.7(5) . . ?
C17 C18 C19 122.3(5) . . ?
C1 C2 C3 119.7(6) . . ?
C4 C3 C2 119.7(6) . . ?
C3 C4 C5 120.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.053
