# Electronic Supplementary Material (ESI) for ChemComm.
# 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_12232sadabs
_database_code_depnum_ccdc_archive 'CCDC 1957001'
loop_
_audit_author_name
_audit_author_address
'Joerg Rust'
;Max Planck Institut fuer Kohlenforschung
Germany
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;


_audit_block_code                LJB-LA-062-01
_audit_creation_date             2019-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 Title
;
_chemical_formula_moiety         'C23 H20 Cl N O S'
_chemical_formula_sum            'C23 H20 Cl N O S'
_chemical_formula_weight         393.91
_chemical_properties_physical    none
_chemical_melting_point          ?
_chemical_absolute_configuration rmad

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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   13.3178(19)
_cell_length_b                   9.6266(14)
_cell_length_c                   15.545(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.661(5)
_cell_angle_gamma                90
_cell_volume                     1909.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9926


_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5259
_cell_measurement_theta_min      2.5193
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.322
_exptl_absorpt_correction_T_max  0.98770
_exptl_absorpt_correction_T_min  0.96425

_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_special_details           
;
 Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  acetonitrile '

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -1.00 0.0600
1.00 0.00 1.00 0.0600
-1.00 0.00 1.00 0.0200
1.00 0.00 -1.00 0.0200
0.00 -1.00 0.00 0.0500
0.00 1.00 0.00 0.0500

_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            53315
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.679
_diffrn_reflns_theta_min         2.381
_diffrn_radiation_source         1\mS
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5548
_reflns_number_total             6405
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'

_computing_data_collection       'APEX3 (Bruker AXS, 2005-2017)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         6405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.7833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0930

_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.

 The minimum and maximum estimated transmissions from the multi-scan
 scaling are 0.9419 and 1.0000 (SADABS).

Highest peak        ?
Deepest hole        ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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_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
Cl1 Cl 0.40415(2) 0.70580(4) 0.35468(2) 0.03080(8) Uani 1 1 d . . . . .
S1 S 0.61086(2) 0.65888(3) 1.02819(2) 0.02184(7) Uani 1 1 d . . . . .
O1 O 0.25433(7) 0.88741(8) 0.77933(6) 0.02811(18) Uani 1 1 d . . . . .
N1 N 0.29908(6) 0.67199(9) 0.74503(5) 0.01519(15) Uani 1 1 d . . . . .
H1 H 0.2809(11) 0.5896(16) 0.7349(9) 0.022(3) Uiso 1 1 d . . . . .
C1 C 0.59878(7) 0.66451(11) 0.82766(6) 0.01726(17) Uani 1 1 d . . . . .
H1A H 0.6186(12) 0.6729(16) 0.7710(10) 0.028(4) Uiso 1 1 d . . . . .
C2 C 0.66994(7) 0.55631(11) 0.88424(6) 0.01773(18) Uani 1 1 d . . . . .
C3 C 0.72851(8) 0.46617(12) 0.84743(7) 0.0220(2) Uani 1 1 d . . . . .
H3 H 0.727401 0.476958 0.786414 0.026 Uiso 1 1 calc R . . . .
C4 C 0.78852(9) 0.36073(12) 0.89848(8) 0.0260(2) Uani 1 1 d . . . . .
H4 H 0.827863 0.300029 0.872382 0.031 Uiso 1 1 calc R . . . .
C5 C 0.79067(9) 0.34458(13) 0.98781(8) 0.0271(2) Uani 1 1 d . . . . .
H5 H 0.830255 0.271370 1.022512 0.032 Uiso 1 1 calc R . . . .
C6 C 0.73509(8) 0.43525(12) 1.02637(7) 0.0238(2) Uani 1 1 d . . . . .
H6 H 0.737478 0.425028 1.087712 0.029 Uiso 1 1 calc R . . . .
C7 C 0.67560(8) 0.54157(11) 0.97500(6) 0.01888(18) Uani 1 1 d . . . . .
C8 C 0.61511(8) 0.81094(11) 0.96571(7) 0.01932(19) Uani 1 1 d . . . . .
C9 C 0.62160(8) 0.93893(13) 1.00893(8) 0.0252(2) Uani 1 1 d . . . . .
H9 H 0.623277 0.942785 1.070391 0.030 Uiso 1 1 calc R . . . .
C10 C 0.62559(9) 1.06045(13) 0.96234(9) 0.0294(2) Uani 1 1 d . . . . .
H10 H 0.628296 1.147748 0.991416 0.035 Uiso 1 1 calc R . . . .
C11 C 0.62565(9) 1.05460(13) 0.87301(9) 0.0285(2) Uani 1 1 d . . . . .
H11 H 0.629856 1.137705 0.841261 0.034 Uiso 1 1 calc R . . . .
C12 C 0.61954(8) 0.92692(12) 0.83036(7) 0.0234(2) Uani 1 1 d . . . . .
H12 H 0.620387 0.923599 0.769489 0.028 Uiso 1 1 calc R . . . .
C13 C 0.61217(7) 0.80326(11) 0.87506(7) 0.01813(18) Uani 1 1 d . . . . .
C14 C 0.48404(7) 0.61320(11) 0.80551(6) 0.01776(18) Uani 1 1 d . . . . .
H14A H 0.479139 0.520353 0.777216 0.021 Uiso 1 1 calc R . . . .
H14B H 0.465055 0.602809 0.862262 0.021 Uiso 1 1 calc R . . . .
C15 C 0.40469(7) 0.71011(10) 0.74289(6) 0.01523(16) Uani 1 1 d . . . . .
H15 H 0.4174(11) 0.8069(14) 0.7661(9) 0.020(3) Uiso 1 1 d . . . . .
C16 C 0.40972(7) 0.70745(10) 0.64654(6) 0.01449(16) Uani 1 1 d . . . . .
C17 C 0.39035(8) 0.58463(11) 0.59653(7) 0.01967(18) Uani 1 1 d . . . . .
H17 H 0.377874 0.501030 0.624276 0.024 Uiso 1 1 calc R . . . .
C18 C 0.38907(9) 0.58297(12) 0.50684(7) 0.0220(2) Uani 1 1 d . . . . .
H18 H 0.375806 0.499203 0.473167 0.026 Uiso 1 1 calc R . . . .
C19 C 0.40747(8) 0.70566(12) 0.46752(6) 0.01965(19) Uani 1 1 d . . . . .
C20 C 0.42677(9) 0.82866(12) 0.51492(7) 0.0224(2) Uani 1 1 d . . . . .
H20 H 0.439060 0.911931 0.486726 0.027 Uiso 1 1 calc R . . . .
C21 C 0.42793(8) 0.82876(11) 0.60482(7) 0.01998(19) Uani 1 1 d . . . . .
H21 H 0.441356 0.912900 0.638086 0.024 Uiso 1 1 calc R . . . .
C22 C 0.23131(8) 0.76443(10) 0.76056(6) 0.01695(17) Uani 1 1 d . . . . .
C23 C 0.12370(8) 0.70903(12) 0.75443(7) 0.02138(19) Uani 1 1 d . . . . .
H23A H 0.106262 0.730020 0.810151 0.032 Uiso 1 1 calc GR . . . .
H23B H 0.122700 0.608229 0.745428 0.032 Uiso 1 1 calc GR . . . .
H23C H 0.072126 0.752817 0.703712 0.032 Uiso 1 1 calc GR . . . .


_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 C19 1.7418(10) . ?
S1 C7 1.7638(11) . ?
S1 C8 1.7666(11) . ?
O1 C22 1.2366(13) . ?
N1 C15 1.4632(13) . ?
N1 C22 1.3377(13) . ?
C1 C2 1.5095(14) . ?
C1 C13 1.5111(14) . ?
C1 C14 1.5479(14) . ?
C2 C3 1.3946(15) . ?
C2 C7 1.3983(13) . ?
C3 C4 1.3911(16) . ?
C4 C5 1.3894(17) . ?
C5 C6 1.3869(17) . ?
C6 C7 1.3965(15) . ?
C8 C9 1.3941(16) . ?
C8 C13 1.4003(14) . ?
C9 C10 1.3849(18) . ?
C10 C11 1.3900(19) . ?
C11 C12 1.3878(17) . ?
C12 C13 1.3959(15) . ?
C14 C15 1.5312(13) . ?
C15 C16 1.5184(13) . ?
C16 C17 1.3978(13) . ?
C16 C21 1.3905(14) . ?
C17 C18 1.3893(14) . ?
C18 C19 1.3837(15) . ?
C19 C20 1.3793(16) . ?
C20 C21 1.3931(15) . ?
C22 C23 1.5063(15) . ?

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 S1 C8 100.13(5) . . ?
C22 N1 C15 122.68(8) . . ?
C2 C1 C13 111.05(8) . . ?
C2 C1 C14 108.92(8) . . ?
C13 C1 C14 111.19(8) . . ?
C3 C2 C1 121.46(9) . . ?
C3 C2 C7 118.43(9) . . ?
C7 C2 C1 120.08(9) . . ?
C4 C3 C2 121.16(10) . . ?
C5 C4 C3 119.71(11) . . ?
C6 C5 C4 120.06(10) . . ?
C5 C6 C7 119.98(10) . . ?
C2 C7 S1 121.05(8) . . ?
C6 C7 S1 118.34(8) . . ?
C6 C7 C2 120.60(10) . . ?
C9 C8 S1 118.34(8) . . ?
C9 C8 C13 120.77(10) . . ?
C13 C8 S1 120.89(8) . . ?
C10 C9 C8 120.06(11) . . ?
C9 C10 C11 119.95(11) . . ?
C12 C11 C10 119.76(11) . . ?
C11 C12 C13 121.35(10) . . ?
C8 C13 C1 120.18(9) . . ?
C12 C13 C1 121.76(9) . . ?
C12 C13 C8 118.05(10) . . ?
C15 C14 C1 113.85(8) . . ?
N1 C15 C14 108.99(8) . . ?
N1 C15 C16 109.44(7) . . ?
C16 C15 C14 113.53(8) . . ?
C17 C16 C15 120.63(8) . . ?
C21 C16 C15 120.59(9) . . ?
C21 C16 C17 118.68(9) . . ?
C18 C17 C16 121.00(9) . . ?
C19 C18 C17 118.73(10) . . ?
C18 C19 Cl1 119.27(8) . . ?
C20 C19 Cl1 118.97(8) . . ?
C20 C19 C18 121.75(9) . . ?
C19 C20 C21 118.89(10) . . ?
C16 C21 C20 120.94(10) . . ?
O1 C22 N1 123.02(10) . . ?
O1 C22 C23 121.39(9) . . ?
N1 C22 C23 115.59(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'


_shelx_SHELXL_version_number     2016/6
