# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_BE34
_database_code_depnum_ccdc_archive 'CCDC 1834668'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Cl N O3 S'
_chemical_formula_sum            'C19 H18 Cl N O3 S'
_chemical_formula_weight         375.85

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   15.5285(11)
_cell_length_b                   12.2909(9)
_cell_length_c                   18.3647(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3505.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8225
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.355
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38891
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4306
_reflns_number_gt                3667
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²+2.0701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4306
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.16507(14) 0.16382(17) 0.54055(12) 0.0465(5) Uani 1 1 d . . . . .
C2 C 0.20697(14) 0.26078(19) 0.52393(12) 0.0501(5) Uani 1 1 d . . . . .
H2 H 0.1993 0.2919 0.4782 0.060 Uiso 1 1 calc R U . . .
C3 C 0.25983(16) 0.3118(2) 0.57401(13) 0.0577(6) Uani 1 1 d . . . . .
H3 H 0.2877 0.3765 0.5622 0.069 Uiso 1 1 calc R U . . .
C4 C 0.27045(16) 0.2653(3) 0.64148(14) 0.0629(7) Uani 1 1 d . . . . .
C5 C 0.22980(19) 0.1701(3) 0.66007(13) 0.0700(8) Uani 1 1 d . . . . .
H5 H 0.2378 0.1397 0.7059 0.084 Uiso 1 1 calc R U . . .
C6 C 0.17653(17) 0.1199(2) 0.60943(14) 0.0592(6) Uani 1 1 d . . . . .
H6 H 0.1482 0.0559 0.6219 0.071 Uiso 1 1 calc R U . . .
C7 C 0.11412(15) 0.10275(17) 0.48391(13) 0.0503(5) Uani 1 1 d . . . . .
H7 H 0.0664 0.0652 0.5081 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1441(2) -0.0287(2) 0.39277(18) 0.0693(7) Uani 1 1 d . . . . .
H8A H 0.0869 -0.0577 0.4012 0.083 Uiso 1 1 calc R U . . .
H8B H 0.1818 -0.0889 0.3807 0.083 Uiso 1 1 calc R U . . .
C9 C 0.14142(16) 0.04867(19) 0.33107(15) 0.0568(6) Uani 1 1 d . . . . .
H9A H 0.1114 0.0158 0.2903 0.068 Uiso 1 1 calc R U . . .
H9B H 0.1996 0.0658 0.3156 0.068 Uiso 1 1 calc R U . . .
C10 C 0.09586(14) 0.15133(16) 0.35365(13) 0.0463(5) Uani 1 1 d . . . . .
C11 C 0.07781(13) 0.17375(16) 0.42387(12) 0.0438(4) Uani 1 1 d . . . . .
C13 C 0.00413(14) 0.34808(16) 0.39536(12) 0.0448(4) Uani 1 1 d . . . . .
C14 C 0.02047(13) 0.26352(15) 0.44435(11) 0.0419(4) Uani 1 1 d . . . . .
C15 C -0.05676(15) 0.42886(19) 0.40963(14) 0.0534(5) Uani 1 1 d . . . . .
H15 H -0.0675 0.4831 0.3755 0.064 Uiso 1 1 calc R U . . .
C16 C -0.10058(15) 0.42753(19) 0.47435(14) 0.0535(5) Uani 1 1 d . . . . .
H16 H -0.1417 0.4807 0.4838 0.064 Uiso 1 1 calc R U . . .
C17 C -0.08420(14) 0.34756(17) 0.52595(13) 0.0470(5) Uani 1 1 d . . . . .
C18 C -0.02425(13) 0.26702(17) 0.51047(12) 0.0455(4) Uani 1 1 d . . . . .
H18 H -0.0134 0.2136 0.5452 0.055 Uiso 1 1 calc R U . . .
C19 C 0.0508(2) 0.1848(3) 0.22428(14) 0.0686(7) Uani 1 1 d . . . . .
H19A H 0.1025 0.1626 0.1997 0.103 Uiso 1 1 calc R U . . .
H19B H 0.0240 0.2427 0.1976 0.103 Uiso 1 1 calc R U . . .
H19C H 0.0119 0.1242 0.2275 0.103 Uiso 1 1 calc R U . . .
C20 C -0.13166(16) 0.3469(2) 0.59732(14) 0.0589(6) Uani 1 1 d . . . . .
H20A H -0.1175 0.4114 0.6243 0.088 Uiso 1 1 calc R U . . .
H20B H -0.1152 0.2839 0.6249 0.088 Uiso 1 1 calc R U . . .
H20C H -0.1926 0.3451 0.5884 0.088 Uiso 1 1 calc R U . . .
Cl1 Cl 0.33632(6) 0.33086(11) 0.70488(5) 0.1018(4) Uani 1 1 d . . . . .
N1 N 0.07211(13) 0.22246(16) 0.29729(11) 0.0521(5) Uani 1 1 d . . . . .
O1 O 0.15212(11) 0.38721(14) 0.33844(11) 0.0624(5) Uani 1 1 d . . . . .
O2 O 0.02564(15) 0.40860(17) 0.26004(10) 0.0740(5) Uani 1 1 d . . . . .
O3 O 0.17370(12) 0.02203(14) 0.45630(11) 0.0639(5) Uani 1 1 d . . . . .
S1 S 0.06785(4) 0.35225(5) 0.31795(3) 0.05045(18) 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
C1 C6 1.387(3) . ?
C1 C2 1.392(3) . ?
C1 C7 1.507(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C4 Cl1 1.747(3) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O3 1.448(3) . ?
C7 C11 1.515(3) . ?
C7 H7 0.9800 . ?
C8 O3 1.400(4) . ?
C8 C9 1.480(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.505(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.348(3) . ?
C10 N1 1.404(3) . ?
C11 C14 1.467(3) . ?
C13 C15 1.396(3) . ?
C13 C14 1.398(3) . ?
C13 S1 1.733(2) . ?
C14 C18 1.399(3) . ?
C15 C16 1.370(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(3) . ?
C17 C20 1.504(3) . ?
C18 H18 0.9300 . ?
C19 N1 1.457(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 S1 1.641(2) . ?
O1 S1 1.4278(19) . ?
O2 S1 1.4284(19) . ?

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
C6 C1 C2 118.3(2) . . ?
C6 C1 C7 120.2(2) . . ?
C2 C1 C7 121.4(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 Cl1 119.8(2) . . ?
C3 C4 Cl1 118.6(2) . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.9(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O3 C7 C1 104.33(18) . . ?
O3 C7 C11 112.18(19) . . ?
C1 C7 C11 114.26(17) . . ?
O3 C7 H7 108.6 . . ?
C1 C7 H7 108.6 . . ?
C11 C7 H7 108.6 . . ?
O3 C8 C9 111.2(2) . . ?
O3 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
O3 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 109.9(2) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 N1 121.55(19) . . ?
C11 C10 C9 122.2(2) . . ?
N1 C10 C9 116.3(2) . . ?
C10 C11 C14 121.68(19) . . ?
C10 C11 C7 120.08(19) . . ?
C14 C11 C7 118.20(19) . . ?
C15 C13 C14 122.1(2) . . ?
C15 C13 S1 121.31(17) . . ?
C14 C13 S1 116.51(16) . . ?
C13 C14 C18 116.46(18) . . ?
C13 C14 C11 120.30(19) . . ?
C18 C14 C11 123.15(19) . . ?
C16 C15 C13 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C13 C15 H15 120.3 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.2(2) . . ?
C16 C17 C20 120.6(2) . . ?
C18 C17 C20 120.2(2) . . ?
C17 C18 C14 122.2(2) . . ?
C17 C18 H18 118.9 . . ?
C14 C18 H18 118.9 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 N1 C19 122.7(2) . . ?
C10 N1 S1 116.45(15) . . ?
C19 N1 S1 120.84(19) . . ?
C8 O3 C7 112.75(19) . . ?
O1 S1 O2 118.10(13) . . ?
O1 S1 N1 108.45(11) . . ?
O2 S1 N1 108.53(12) . . ?
O1 S1 C13 108.42(11) . . ?
O2 S1 C13 111.29(12) . . ?
N1 S1 C13 100.60(10) . . ?

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 -174.3(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C2 C3 C4 Cl1 -179.31(19) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
Cl1 C4 C5 C6 179.0(2) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C7 C1 C6 C5 174.0(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C6 C1 C7 O3 -79.4(2) . . . . ?
C2 C1 C7 O3 95.7(2) . . . . ?
C6 C1 C7 C11 157.7(2) . . . . ?
C2 C1 C7 C11 -27.1(3) . . . . ?
O3 C8 C9 C10 -49.3(3) . . . . ?
C8 C9 C10 C11 12.4(3) . . . . ?
C8 C9 C10 N1 -166.9(2) . . . . ?
N1 C10 C11 C14 10.3(3) . . . . ?
C9 C10 C11 C14 -169.00(19) . . . . ?
N1 C10 C11 C7 -172.21(19) . . . . ?
C9 C10 C11 C7 8.5(3) . . . . ?
O3 C7 C11 C10 6.0(3) . . . . ?
C1 C7 C11 C10 124.5(2) . . . . ?
O3 C7 C11 C14 -176.37(17) . . . . ?
C1 C7 C11 C14 -57.9(3) . . . . ?
C15 C13 C14 C18 -3.2(3) . . . . ?
S1 C13 C14 C18 173.14(15) . . . . ?
C15 C13 C14 C11 173.2(2) . . . . ?
S1 C13 C14 C11 -10.4(3) . . . . ?
C10 C11 C14 C13 -19.9(3) . . . . ?
C7 C11 C14 C13 162.54(19) . . . . ?
C10 C11 C14 C18 156.3(2) . . . . ?
C7 C11 C14 C18 -21.3(3) . . . . ?
C14 C13 C15 C16 1.8(3) . . . . ?
S1 C13 C15 C16 -174.46(18) . . . . ?
C13 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
C15 C16 C17 C20 179.3(2) . . . . ?
C16 C17 C18 C14 0.0(3) . . . . ?
C20 C17 C18 C14 179.1(2) . . . . ?
C13 C14 C18 C17 2.4(3) . . . . ?
C11 C14 C18 C17 -173.93(19) . . . . ?
C11 C10 N1 C19 -149.1(2) . . . . ?
C9 C10 N1 C19 30.2(3) . . . . ?
C11 C10 N1 S1 29.9(3) . . . . ?
C9 C10 N1 S1 -150.76(16) . . . . ?
C9 C8 O3 C7 67.4(3) . . . . ?
C1 C7 O3 C8 -167.8(2) . . . . ?
C11 C7 O3 C8 -43.6(3) . . . . ?
C10 N1 S1 O1 62.8(2) . . . . ?
C19 N1 S1 O1 -118.1(2) . . . . ?
C10 N1 S1 O2 -167.78(18) . . . . ?
C19 N1 S1 O2 11.3(2) . . . . ?
C10 N1 S1 C13 -50.89(19) . . . . ?
C19 N1 S1 C13 128.2(2) . . . . ?
C15 C13 S1 O1 103.8(2) . . . . ?
C14 C13 S1 O1 -72.64(18) . . . . ?
C15 C13 S1 O2 -27.7(2) . . . . ?
C14 C13 S1 O2 155.87(17) . . . . ?
C15 C13 S1 N1 -142.53(19) . . . . ?
C14 C13 S1 N1 41.05(18) . . . . ?

_refine_diff_density_max         1.017
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.060

