# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_y
_database_code_depnum_ccdc_archive 'CCDC 1582236'
_audit_update_record             
;
2017-10-26 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl N O2 S'
_chemical_formula_weight         317.79

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'
Cl Cl 0.1484 0.1585 '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   C2/c

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

_cell_length_a                   24.908(3)
_cell_length_b                   13.4385(17)
_cell_length_c                   8.7528(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.042(6)
_cell_angle_gamma                90.00
_cell_volume                     2925.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9541
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9195
_exptl_absorpt_correction_T_max  0.9304
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            23376
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3340
_reflns_number_gt                2801
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0346P)²+4.3790P] 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         3340
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl -1.04483(3) -0.28669(4) -1.97009(8) 0.06634(19) Uani 1 1 d . . .
S1 S -1.231370(19) 0.21707(4) -1.75324(6) 0.04187(14) Uani 1 1 d . . .
O1 O -1.13648(6) 0.49032(10) -2.03278(17) 0.0485(4) Uani 1 1 d . . .
O2 O -1.20196(6) 0.60043(11) -1.9908(2) 0.0584(4) Uani 1 1 d . . .
N1 N -1.20747(6) 0.43911(12) -1.89453(19) 0.0418(4) Uani 1 1 d . . .
C1 C -1.07887(8) -0.17572(15) -1.9369(2) 0.0431(4) Uani 1 1 d . . .
C2 C -1.13410(8) -0.17592(15) -1.9391(2) 0.0440(4) Uani 1 1 d . . .
H2 H -1.1533 -0.2344 -1.9580 0.053 Uiso 1 1 calc R . .
C3 C -1.16074(8) -0.08749(14) -1.9126(2) 0.0419(4) Uani 1 1 d . . .
H3 H -1.1981 -0.0872 -1.9137 0.050 Uiso 1 1 calc R . .
C4 C -1.13278(7) 0.00096(14) -1.8844(2) 0.0369(4) Uani 1 1 d . . .
C5 C -1.07667(8) -0.00259(15) -1.8801(3) 0.0464(5) Uani 1 1 d . . .
H5 H -1.0571 0.0551 -1.8584 0.056 Uiso 1 1 calc R . .
C6 C -1.04966(8) -0.09008(16) -1.9072(3) 0.0487(5) Uani 1 1 d . . .
H6 H -1.0123 -0.0912 -1.9054 0.058 Uiso 1 1 calc R . .
C7 C -1.16167(7) 0.09511(14) -1.8568(2) 0.0369(4) Uani 1 1 d . . .
C8 C -1.20700(7) 0.09969(14) -1.7740(2) 0.0410(4) Uani 1 1 d . . .
H8 H -1.2229 0.0438 -1.7330 0.049 Uiso 1 1 calc R . .
C9 C -1.14661(7) 0.19125(13) -1.9078(2) 0.0366(4) Uani 1 1 d . . .
C10 C -1.18032(7) 0.26465(14) -1.8566(2) 0.0372(4) Uani 1 1 d . . .
C11 C -1.10306(8) 0.21488(14) -2.0165(2) 0.0440(4) Uani 1 1 d . . .
H11A H -1.1032 0.1643 -2.0956 0.053 Uiso 1 1 calc R . .
H11B H -1.0684 0.2127 -1.9608 0.053 Uiso 1 1 calc R . .
C12 C -1.11049(8) 0.31779(15) -2.0920(2) 0.0442(4) Uani 1 1 d . . .
H12A H -1.0781 0.3362 -2.1422 0.053 Uiso 1 1 calc R . .
H12B H -1.1401 0.3156 -2.1686 0.053 Uiso 1 1 calc R . .
C13 C -1.17379(7) 0.36609(14) -1.8985(2) 0.0367(4) Uani 1 1 d . . .
C14 C -1.12208(7) 0.39407(14) -1.9701(2) 0.0394(4) Uani 1 1 d . . .
C15 C -1.07550(8) 0.40955(18) -1.8526(3) 0.0545(5) Uani 1 1 d . . .
H15A H -1.0448 0.4337 -1.9030 0.082 Uiso 1 1 calc R . .
H15B H -1.0667 0.3475 -1.8030 0.082 Uiso 1 1 calc R . .
H15C H -1.0856 0.4572 -1.7777 0.082 Uiso 1 1 calc R . .
C16 C -1.18382(8) 0.51855(14) -1.9730(2) 0.0438(4) Uani 1 1 d . . .


_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
Cl1 C1 1.747(2) . ?
S1 C8 1.703(2) . ?
S1 C10 1.7222(18) . ?
O1 C16 1.369(2) . ?
O1 C14 1.443(2) . ?
O2 C16 1.197(2) . ?
N1 C13 1.293(2) . ?
N1 C16 1.415(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.379(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 C7 1.482(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.375(2) . ?
C7 C9 1.424(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(2) . ?
C9 C11 1.514(2) . ?
C10 C13 1.423(3) . ?
C11 C12 1.540(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.519(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.510(2) . ?
C14 C15 1.523(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C8 S1 C10 90.61(9) . . ?
C16 O1 C14 107.75(14) . . ?
C13 N1 C16 105.80(15) . . ?
C2 C1 C6 121.45(18) . . ?
C2 C1 Cl1 119.35(16) . . ?
C6 C1 Cl1 119.20(16) . . ?
C1 C2 C3 118.92(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.44(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 117.76(18) . . ?
C3 C4 C7 121.00(16) . . ?
C5 C4 C7 121.24(17) . . ?
C6 C5 C4 121.34(18) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 119.07(18) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C9 111.22(16) . . ?
C8 C7 C4 122.93(17) . . ?
C9 C7 C4 125.85(16) . . ?
C7 C8 S1 113.88(14) . . ?
C7 C8 H8 123.1 . . ?
S1 C8 H8 123.1 . . ?
C10 C9 C7 111.76(16) . . ?
C10 C9 C11 121.39(16) . . ?
C7 C9 C11 126.63(16) . . ?
C9 C10 C13 121.27(16) . . ?
C9 C10 S1 112.50(14) . . ?
C13 C10 S1 126.06(14) . . ?
C9 C11 C12 112.61(15) . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C14 C12 C11 109.12(16) . . ?
C14 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C14 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N1 C13 C10 129.56(17) . . ?
N1 C13 C14 113.04(16) . . ?
C10 C13 C14 117.21(15) . . ?
O1 C14 C13 100.42(14) . . ?
O1 C14 C12 112.99(16) . . ?
C13 C14 C12 108.77(16) . . ?
O1 C14 C15 107.42(16) . . ?
C13 C14 C15 112.94(16) . . ?
C12 C14 C15 113.60(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 O1 122.13(18) . . ?
O2 C16 N1 126.40(18) . . ?
O1 C16 N1 111.45(16) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.044
