# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_x_a
_database_code_depnum_ccdc_archive 'CCDC 1868011'
_audit_update_record             
;
2018-09-15 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl N O2 S'
_chemical_formula_weight         373.88

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'
Cl Cl 0.1484 0.1585 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.5425(5)
_cell_length_b                   20.2515(9)
_cell_length_c                   8.2218(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.176(2)
_cell_angle_gamma                90
_cell_volume                     1920.48(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    8070
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.67

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22022
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.766
_diffrn_reflns_theta_max         28.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4969
_reflns_number_gt                3986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.5039P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4969
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80473(3) 0.40207(2) 0.28398(4) 0.04058(11) Uani 1 1 d . . . . .
H1 H 0.7655(19) 0.3368(10) 0.742(2) 0.060(6) Uiso 1 1 d . . . . .
CL1 Cl 0.34272(5) 0.25622(3) 0.07163(8) 0.07812(18) Uani 1 1 d . . . . .
N1 N 0.79011(13) 0.49103(7) 0.71482(16) 0.0500(3) Uani 1 1 d . . . . .
O1 O 0.67840(12) 0.56116(6) 0.48944(15) 0.0569(3) Uani 1 1 d . . . . .
C1 C 0.88812(12) 0.39143(7) 0.63810(17) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.67823(10) 0.52383(6) 0.23345(13) 0.0466(3) Uani 1 1 d . . . . .
H2 H 0.890(2) 0.2498(13) 0.813(3) 0.082(7) Uiso 1 1 d . . . . .
C2 C 0.84494(17) 0.33735(9) 0.7183(2) 0.0536(4) Uani 1 1 d . . . . .
C3 C 0.9184(2) 0.28562(10) 0.7643(3) 0.0671(5) Uani 1 1 d . . . . .
H3 H 1.086(2) 0.2514(12) 0.766(3) 0.081(7) Uiso 1 1 d . . . . .
C4 C 1.0337(2) 0.28822(10) 0.7293(3) 0.0681(6) Uani 1 1 d . . . . .
H4 H 1.155(3) 0.3439(14) 0.622(4) 0.105(9) Uiso 1 1 d . . . . .
C5 C 1.07701(17) 0.34129(11) 0.6493(3) 0.0665(5) Uani 1 1 d . . . . .
H5 H 1.032(2) 0.4305(12) 0.547(3) 0.074(7) Uiso 1 1 d . . . . .
C7 C 0.81260(11) 0.44927(7) 0.59449(16) 0.0342(3) Uani 1 1 d . . . . .
H7 H 0.3925(17) 0.3573(9) 0.299(2) 0.054(5) Uiso 1 1 d . . . . .
C6 C 1.00431(14) 0.39311(9) 0.6022(2) 0.0513(4) Uani 1 1 d . . . . .
H6 H 0.5614(16) 0.4116(9) 0.376(2) 0.049(5) Uiso 1 1 d . . . . .
C8 C 0.77151(12) 0.45969(7) 0.43556(16) 0.0352(3) Uani 1 1 d . . . . .
H8 H 0.5798(18) 0.2465(10) -0.010(3) 0.062(6) Uiso 1 1 d . . . . .
C9 C 0.70660(12) 0.51900(7) 0.39226(17) 0.0381(3) Uani 1 1 d . . . . .
H9 H 0.7461(19) 0.3042(10) 0.074(2) 0.063(6) Uiso 1 1 d . . . . .
C10 C 0.60876(17) 0.58046(10) 0.1814(3) 0.0573(5) Uani 1 1 d . . . . .
H10 H 0.7482(18) 0.5248(11) 0.686(2) 0.061(6) Uiso 1 1 d . . . . .
C11 C 0.4834(2) 0.56656(15) 0.1989(3) 0.0905(8) Uani 1 1 d . . . . .
H11A H 0.438589 0.603340 0.158204 0.136 Uiso 1 1 calc R U . . .
H11B H 0.468408 0.559746 0.311702 0.136 Uiso 1 1 calc R U . . .
H11C H 0.462377 0.527619 0.138110 0.136 Uiso 1 1 calc R U . . .
H11 H 0.8877(19) 0.4537(11) 0.897(3) 0.068(6) Uiso 1 1 d . . . . .
C12 C 0.82810(18) 0.48670(10) 0.8852(2) 0.0532(4) Uani 1 1 d . . . . .
H12 H 0.759(2) 0.4741(11) 0.950(3) 0.071(6) Uiso 1 1 d . . . . .
C13 C 0.87070(16) 0.55018(11) 0.9530(2) 0.0583(5) Uani 1 1 d . . . . .
H13 H 0.624(2) 0.5856(12) 0.066(3) 0.078(7) Uiso 1 1 d . . . . .
C14 C 0.8916(3) 0.60373(15) 0.8755(4) 0.0875(8) Uani 1 1 d . . . . .
H14 H 0.640(2) 0.6192(13) 0.235(3) 0.084(8) Uiso 1 1 d . . . . .
C15 C 0.67121(13) 0.36245(7) 0.23438(16) 0.0366(3) Uani 1 1 d . . . . .
H15 H 0.882(2) 0.5506(12) 1.079(3) 0.087(7) Uiso 1 1 d . . . . .
C16 C 0.56595(14) 0.37812(8) 0.30133(18) 0.0407(3) Uani 1 1 d . . . . .
H16 H 0.922(3) 0.6405(17) 0.937(4) 0.117(10) Uiso 1 1 d . . . . .
C17 C 0.46514(15) 0.34527(8) 0.2518(2) 0.0452(3) Uani 1 1 d . . . . .
H17 H 0.881(2) 0.6041(13) 0.760(4) 0.095(9) Uiso 1 1 d . . . . .
C18 C 0.47012(15) 0.29647(8) 0.1355(2) 0.0483(4) Uani 1 1 d . . . . .
C19 C 0.57355(17) 0.27969(9) 0.0677(2) 0.0560(4) Uani 1 1 d . . . . .
C20 C 0.67360(16) 0.31283(9) 0.1172(2) 0.0493(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
S1 C8 1.7601(14) . ?
S1 C15 1.7712(15) . ?
CL1 C18 1.7447(17) . ?
N1 C7 1.3346(19) . ?
N1 C12 1.455(2) . ?
N1 H10 0.87(2) . ?
O1 C9 1.2219(18) . ?
C1 C2 1.381(2) . ?
C1 C6 1.384(2) . ?
C1 C7 1.4956(19) . ?
O2 C9 1.3376(17) . ?
O2 C10 1.455(2) . ?
C2 C3 1.391(3) . ?
C2 H1 0.94(2) . ?
C3 C4 1.373(3) . ?
C3 H2 0.89(3) . ?
C4 C5 1.365(3) . ?
C4 H3 1.00(2) . ?
C5 C6 1.389(2) . ?
C5 H4 0.94(3) . ?
C7 C8 1.3892(19) . ?
C6 H5 0.94(2) . ?
C8 C9 1.4528(19) . ?
C10 C11 1.486(3) . ?
C10 H13 0.98(2) . ?
C10 H14 0.96(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.478(3) . ?
C12 H11 0.96(2) . ?
C12 H12 1.00(2) . ?
C13 C14 1.285(4) . ?
C13 H15 1.04(3) . ?
C14 H16 0.96(3) . ?
C14 H17 0.95(3) . ?
C15 C16 1.389(2) . ?
C15 C20 1.393(2) . ?
C16 C17 1.388(2) . ?
C16 H6 0.918(19) . ?
C17 C18 1.378(2) . ?
C17 H7 0.97(2) . ?
C18 C19 1.379(3) . ?
C19 C20 1.383(3) . ?
C19 H8 0.93(2) . ?
C20 H9 0.94(2) . ?

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 C15 104.61(7) . . ?
C7 N1 C12 128.01(14) . . ?
C7 N1 H10 115.0(14) . . ?
C12 N1 H10 117.0(14) . . ?
C2 C1 C6 119.42(15) . . ?
C2 C1 C7 121.18(14) . . ?
C6 C1 C7 119.36(14) . . ?
C9 O2 C10 117.19(13) . . ?
C1 C2 C3 119.97(18) . . ?
C1 C2 H1 118.5(12) . . ?
C3 C2 H1 121.6(12) . . ?
C4 C3 C2 119.99(19) . . ?
C4 C3 H2 119.7(16) . . ?
C2 C3 H2 120.2(16) . . ?
C5 C4 C3 120.47(17) . . ?
C5 C4 H3 120.3(14) . . ?
C3 C4 H3 119.2(14) . . ?
C4 C5 C6 120.02(19) . . ?
C4 C5 H4 122.2(17) . . ?
C6 C5 H4 117.7(18) . . ?
N1 C7 C8 122.14(13) . . ?
N1 C7 C1 116.53(12) . . ?
C8 C7 C1 121.30(12) . . ?
C1 C6 C5 120.12(18) . . ?
C1 C6 H5 118.2(14) . . ?
C5 C6 H5 121.7(14) . . ?
C7 C8 C9 120.70(12) . . ?
C7 C8 S1 119.31(10) . . ?
C9 C8 S1 119.92(10) . . ?
O1 C9 O2 121.72(13) . . ?
O1 C9 C8 124.42(13) . . ?
O2 C9 C8 113.86(12) . . ?
O2 C10 C11 110.48(18) . . ?
O2 C10 H13 104.4(14) . . ?
C11 C10 H13 109.4(14) . . ?
O2 C10 H14 108.3(15) . . ?
C11 C10 H14 117.2(15) . . ?
H13 C10 H14 106(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 113.23(16) . . ?
N1 C12 H11 109.0(13) . . ?
C13 C12 H11 110.0(13) . . ?
N1 C12 H12 108.1(13) . . ?
C13 C12 H12 106.2(13) . . ?
H11 C12 H12 110.3(18) . . ?
C14 C13 C12 127.8(2) . . ?
C14 C13 H15 117.9(14) . . ?
C12 C13 H15 114.2(14) . . ?
C13 C14 H16 117.5(19) . . ?
C13 C14 H17 118.9(17) . . ?
H16 C14 H17 123(3) . . ?
C16 C15 C20 118.64(15) . . ?
C16 C15 S1 124.86(11) . . ?
C20 C15 S1 116.48(12) . . ?
C17 C16 C15 120.67(14) . . ?
C17 C16 H6 118.8(12) . . ?
C15 C16 H6 120.5(12) . . ?
C18 C17 C16 119.40(15) . . ?
C18 C17 H7 121.2(11) . . ?
C16 C17 H7 119.4(11) . . ?
C17 C18 C19 121.12(16) . . ?
C17 C18 CL1 119.15(14) . . ?
C19 C18 CL1 119.73(13) . . ?
C18 C19 C20 119.18(15) . . ?
C18 C19 H8 123.1(13) . . ?
C20 C19 H8 117.8(13) . . ?
C19 C20 C15 120.98(16) . . ?
C19 C20 H9 123.0(13) . . ?
C15 C20 H9 116.0(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C1 C2 C3 -176.92(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C12 N1 C7 C8 -179.36(17) . . . . ?
C12 N1 C7 C1 -1.4(3) . . . . ?
C2 C1 C7 N1 77.43(19) . . . . ?
C6 C1 C7 N1 -100.39(18) . . . . ?
C2 C1 C7 C8 -104.59(18) . . . . ?
C6 C1 C7 C8 77.59(19) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C7 C1 C6 C5 176.71(17) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
N1 C7 C8 C9 3.2(2) . . . . ?
C1 C7 C8 C9 -174.67(13) . . . . ?
N1 C7 C8 S1 -179.81(12) . . . . ?
C1 C7 C8 S1 2.32(19) . . . . ?
C15 S1 C8 C7 109.90(12) . . . . ?
C15 S1 C8 C9 -73.09(13) . . . . ?
C10 O2 C9 O1 -2.0(2) . . . . ?
C10 O2 C9 C8 177.40(14) . . . . ?
C7 C8 C9 O1 -4.0(2) . . . . ?
S1 C8 C9 O1 178.99(13) . . . . ?
C7 C8 C9 O2 176.57(13) . . . . ?
S1 C8 C9 O2 -0.40(18) . . . . ?
C9 O2 C10 C11 -85.5(2) . . . . ?
C7 N1 C12 C13 135.52(19) . . . . ?
N1 C12 C13 C14 -10.0(3) . . . . ?
C8 S1 C15 C16 2.27(14) . . . . ?
C8 S1 C15 C20 -178.90(12) . . . . ?
C20 C15 C16 C17 -0.4(2) . . . . ?
S1 C15 C16 C17 178.44(12) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C16 C17 C18 CL1 -179.06(12) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
CL1 C18 C19 C20 178.77(14) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C16 C15 C20 C19 0.1(2) . . . . ?
S1 C15 C20 C19 -178.83(14) . . . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041

