# Electronic Supplementary Material (ESI) for ChemComm.
# 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_chenman
_database_code_depnum_ccdc_archive 'CCDC 1524458'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.38

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   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0767(10)
_cell_length_b                   10.7938(6)
_cell_length_c                   8.1475(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.9760(10)
_cell_angle_gamma                90.00
_cell_volume                     1588.76(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3266
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      26.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9056
_exptl_absorpt_correction_T_max  0.9809
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11473
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3958
_reflns_number_gt                2653
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0515P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3958
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1072
_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
N1 N 0.06169(8) 0.22026(14) 0.02278(18) 0.0592(4) Uani 1 1 d . . .
O1 O 0.26381(8) -0.03713(13) 0.34109(17) 0.0770(4) Uani 1 1 d . . .
O2 O 0.35178(8) 0.13694(16) 0.36745(19) 0.0876(5) Uani 1 1 d . . .
O3 O 0.13714(7) 0.21096(13) -0.01388(15) 0.0686(4) Uani 1 1 d . . .
S1 S 0.30001(3) 0.06647(5) 0.26847(6) 0.06119(16) Uani 1 1 d . . .
C1 C -0.08417(9) 0.21203(15) 0.1392(2) 0.0543(4) Uani 1 1 d . . .
H1 H -0.0721 0.2785 0.0725 0.065 Uiso 1 1 calc R . .
C2 C -0.15499(10) 0.20093(18) 0.1944(2) 0.0641(5) Uani 1 1 d . . .
H2 H -0.1904 0.2601 0.1651 0.077 Uiso 1 1 calc R . .
C3 C -0.17390(11) 0.10251(19) 0.2931(2) 0.0647(5) Uani 1 1 d . . .
H3 H -0.2217 0.0959 0.3309 0.078 Uiso 1 1 calc R . .
C4 C -0.12176(11) 0.01469(18) 0.3351(2) 0.0625(5) Uani 1 1 d . . .
H4 H -0.1345 -0.0522 0.4003 0.075 Uiso 1 1 calc R . .
C5 C -0.05033(10) 0.02505(16) 0.2809(2) 0.0544(4) Uani 1 1 d . . .
H5 H -0.0153 -0.0347 0.3105 0.065 Uiso 1 1 calc R . .
C6 C -0.03038(9) 0.12425(14) 0.18238(18) 0.0452(3) Uani 1 1 d . . .
C7 C 0.04516(9) 0.13517(14) 0.12398(18) 0.0463(4) Uani 1 1 d . . .
C8 C 0.10860(9) 0.05266(16) 0.1730(2) 0.0551(4) Uani 1 1 d . . .
H8A H 0.0999 -0.0320 0.1375 0.066 Uiso 1 1 calc R . .
H8B H 0.1182 0.0539 0.2909 0.066 Uiso 1 1 calc R . .
C9 C 0.17139(9) 0.11144(16) 0.0823(2) 0.0549(4) Uani 1 1 d . . .
H9 H 0.1930 0.0505 0.0087 0.066 Uiso 1 1 calc R . .
C10 C 0.23226(10) 0.17117(16) 0.1886(2) 0.0589(4) Uani 1 1 d . . .
H10A H 0.2098 0.2131 0.2796 0.071 Uiso 1 1 calc R . .
H10B H 0.2567 0.2335 0.1240 0.071 Uiso 1 1 calc R . .
C11 C 0.34416(9) 0.01445(17) 0.0926(2) 0.0564(4) Uani 1 1 d . . .
C12 C 0.39142(11) 0.0923(2) 0.0128(3) 0.0773(6) Uani 1 1 d . . .
H12 H 0.4016 0.1711 0.0540 0.093 Uiso 1 1 calc R . .
C13 C 0.42356(13) 0.0520(2) -0.1291(3) 0.0892(7) Uani 1 1 d . . .
H13 H 0.4549 0.1050 -0.1837 0.107 Uiso 1 1 calc R . .
C14 C 0.41031(11) -0.0648(2) -0.1918(3) 0.0768(6) Uani 1 1 d . . .
C15 C 0.36341(12) -0.1407(2) -0.1100(3) 0.0761(6) Uani 1 1 d . . .
H15 H 0.3541 -0.2201 -0.1501 0.091 Uiso 1 1 calc R . .
C16 C 0.32959(11) -0.10216(18) 0.0309(3) 0.0683(5) Uani 1 1 d . . .
H16 H 0.2972 -0.1546 0.0836 0.082 Uiso 1 1 calc R . .
C17 C 0.44631(15) -0.1053(3) -0.3479(3) 0.1162(10) Uani 1 1 d . . .
H17A H 0.4168 -0.0779 -0.4412 0.174 Uiso 1 1 calc R . .
H17B H 0.4501 -0.1940 -0.3496 0.174 Uiso 1 1 calc R . .
H17C H 0.4949 -0.0697 -0.3519 0.174 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
N1 C7 1.277(2) . ?
N1 O3 1.4099(18) . ?
O1 S1 1.4337(14) . ?
O2 S1 1.4327(14) . ?
O3 C9 1.455(2) . ?
S1 C11 1.7560(19) . ?
S1 C10 1.7737(18) . ?
C1 C2 1.377(2) . ?
C1 C6 1.394(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.466(2) . ?
C7 C8 1.496(2) . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.520(2) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.377(3) . ?
C11 C16 1.377(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 C17 1.513(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C7 N1 O3 109.59(13) . . ?
N1 O3 C9 109.59(12) . . ?
O2 S1 O1 118.71(10) . . ?
O2 S1 C11 108.82(9) . . ?
O1 S1 C11 108.31(9) . . ?
O2 S1 C10 107.31(9) . . ?
O1 S1 C10 109.22(9) . . ?
C11 S1 C10 103.40(8) . . ?
C2 C1 C6 120.43(16) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.55(17) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.64(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.36(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.60(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.42(16) . . ?
C5 C6 C7 120.74(14) . . ?
C1 C6 C7 120.84(14) . . ?
N1 C7 C6 120.59(14) . . ?
N1 C7 C8 113.99(15) . . ?
C6 C7 C8 125.42(14) . . ?
C7 C8 C9 101.58(13) . . ?
C7 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
C7 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
O3 C9 C8 105.07(13) . . ?
O3 C9 C10 106.25(14) . . ?
C8 C9 C10 116.05(14) . . ?
O3 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C10 C9 H9 109.7 . . ?
C9 C10 S1 114.58(12) . . ?
C9 C10 H10A 108.6 . . ?
S1 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
S1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C16 119.93(19) . . ?
C12 C11 S1 119.79(15) . . ?
C16 C11 S1 120.24(14) . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 121.7(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 C17 121.8(2) . . ?
C13 C14 C17 120.1(2) . . ?
C14 C15 C16 121.5(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 119.59(19) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.035
