# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_BE02m
_database_code_depnum_ccdc_archive 'CCDC 1526953'
_audit_update_record             
;
2017-01-12 deposited with the CCDC.
2017-08-25 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         'C23 H17 Cl N2 S'
_chemical_formula_sum            'C23 H17 Cl N2 S'
_chemical_formula_weight         388.89

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'
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                   8.3120(5)
_cell_length_b                   10.2393(7)
_cell_length_c                   21.6965(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.0530(10)
_cell_angle_gamma                90
_cell_volume                     1832.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7530
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.333
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_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            20958
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.202
_diffrn_reflns_theta_max         28.221
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4434
_reflns_number_gt                3741
_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)+(0.0727P)²+0.4981P] 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         4434
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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 0.10511(19) 0.86897(15) 0.36730(7) 0.0366(3) Uani 1 1 d . . . . .
C2 C 0.18476(19) 0.79723(15) 0.31912(7) 0.0347(3) Uani 1 1 d . . . . .
C3 C 0.17265(19) 0.65940(15) 0.30662(7) 0.0349(3) Uani 1 1 d . . . . .
C4 C 0.25970(19) 0.68907(15) 0.21039(7) 0.0358(3) Uani 1 1 d . . . . .
C5 C 0.2737(2) 0.63793(16) 0.15077(8) 0.0390(3) Uani 1 1 d . . . . .
H5 H 0.2426 0.5524 0.1411 0.047 Uiso 1 1 calc R U . . .
C6 C 0.33284(19) 0.71488(17) 0.10775(7) 0.0379(3) Uani 1 1 d . . . . .
C7 C 0.3900(2) 0.84283(17) 0.12064(8) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.3770(2) 0.89180(17) 0.17860(8) 0.0434(4) Uani 1 1 d . . . . .
H8 H 0.4158 0.9754 0.1884 0.052 Uiso 1 1 calc R U . . .
C9 C 0.30681(19) 0.81959(16) 0.22401(7) 0.0366(3) Uani 1 1 d . . . . .
C10 C 0.26584(19) 0.87340(16) 0.28045(8) 0.0372(3) Uani 1 1 d . . . . .
C11 C 0.2971(2) 1.01411(17) 0.29823(9) 0.0482(4) Uani 1 1 d . . . . .
H11A H 0.2104 1.0685 0.2783 0.058 Uiso 1 1 calc R U . . .
H11B H 0.3982 1.0428 0.2846 0.058 Uiso 1 1 calc R U . . .
C12 C 0.3064(2) 1.02726(18) 0.36826(9) 0.0488(4) Uani 1 1 d . . . . .
H12A H 0.3992 0.9788 0.3878 0.059 Uiso 1 1 calc R U . . .
H12B H 0.3214 1.1184 0.3798 0.059 Uiso 1 1 calc R U . . .
C13 C 0.13533(19) 0.56173(15) 0.35222(7) 0.0357(3) Uani 1 1 d . . . . .
C14 C 0.1398(2) 0.56795(17) 0.41550(8) 0.0447(4) Uani 1 1 d . . . . .
H14 H 0.1611 0.6441 0.4384 0.054 Uiso 1 1 calc R U . . .
C15 C 0.1087(2) 0.4460(2) 0.44221(9) 0.0514(5) Uani 1 1 d . . . . .
H15 H 0.1075 0.4332 0.4846 0.062 Uiso 1 1 calc R U . . .
C16 C 0.0807(2) 0.3499(2) 0.39946(10) 0.0525(5) Uani 1 1 d . . . . .
H16 H 0.0563 0.2641 0.4089 0.063 Uiso 1 1 calc R U . . .
C17 C -0.0564(2) 0.82635(15) 0.38334(7) 0.0373(3) Uani 1 1 d . . . . .
C18 C -0.0968(2) 0.84718(17) 0.44309(8) 0.0457(4) Uani 1 1 d . . . . .
H18 H -0.0197 0.8802 0.4738 0.055 Uiso 1 1 calc R U . . .
C19 C -0.2514(3) 0.81882(19) 0.45674(10) 0.0539(5) Uani 1 1 d . . . . .
H19 H -0.2772 0.8314 0.4968 0.065 Uiso 1 1 calc R U . . .
C20 C -0.3669(3) 0.77217(19) 0.41122(11) 0.0566(5) Uani 1 1 d . . . . .
H20 H -0.4708 0.7538 0.4204 0.068 Uiso 1 1 calc R U . . .
C21 C -0.3282(2) 0.75266(19) 0.35173(10) 0.0535(5) Uani 1 1 d . . . . .
H21 H -0.4066 0.7221 0.3209 0.064 Uiso 1 1 calc R U . . .
C22 C -0.1731(2) 0.77850(17) 0.33795(8) 0.0430(4) Uani 1 1 d . . . . .
H22 H -0.1472 0.7637 0.2980 0.052 Uiso 1 1 calc R U . . .
C23 C 0.4619(3) 0.9231(2) 0.07279(10) 0.0577(5) Uani 1 1 d . . . . .
H23A H 0.3779 0.9485 0.0407 0.086 Uiso 1 1 calc R U . . .
H23B H 0.5418 0.8723 0.0551 0.086 Uiso 1 1 calc R U . . .
H23C H 0.5120 0.9997 0.0921 0.086 Uiso 1 1 calc R U . . .
Cl1 Cl 0.33865(6) 0.65248(5) 0.03339(2) 0.05275(15) Uani 1 1 d . . . . .
N1 N 0.15918(18) 0.97804(15) 0.39064(7) 0.0447(3) Uani 1 1 d . . . . .
N2 N 0.20329(17) 0.60922(13) 0.25328(6) 0.0385(3) Uani 1 1 d . . . . .
S1 S 0.09554(7) 0.40433(5) 0.32637(2) 0.05201(16) 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 N1 1.284(2) . ?
C1 C17 1.493(2) . ?
C1 C2 1.497(2) . ?
C2 C10 1.380(2) . ?
C2 C3 1.438(2) . ?
C3 N2 1.319(2) . ?
C3 C13 1.466(2) . ?
C4 N2 1.364(2) . ?
C4 C9 1.414(2) . ?
C4 C5 1.413(2) . ?
C5 C6 1.359(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(2) . ?
C6 Cl1 1.7414(16) . ?
C7 C8 1.370(2) . ?
C7 C23 1.504(2) . ?
C8 C9 1.414(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.422(2) . ?
C10 C11 1.506(2) . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.461(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.370(2) . ?
C13 S1 1.7251(16) . ?
C14 C15 1.414(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.353(3) . ?
C15 H15 0.9300 . ?
C16 S1 1.6997(19) . ?
C16 H16 0.9300 . ?
C17 C22 1.385(2) . ?
C17 C18 1.395(2) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
N1 C1 C17 116.32(14) . . ?
N1 C1 C2 122.59(15) . . ?
C17 C1 C2 120.46(14) . . ?
C10 C2 C3 117.89(14) . . ?
C10 C2 C1 115.98(14) . . ?
C3 C2 C1 125.91(14) . . ?
N2 C3 C2 122.07(14) . . ?
N2 C3 C13 113.94(14) . . ?
C2 C3 C13 123.89(14) . . ?
N2 C4 C9 122.24(14) . . ?
N2 C4 C5 118.42(14) . . ?
C9 C4 C5 119.33(14) . . ?
C6 C5 C4 119.41(15) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 122.96(15) . . ?
C5 C6 Cl1 118.50(13) . . ?
C7 C6 Cl1 118.53(12) . . ?
C8 C7 C6 117.36(15) . . ?
C8 C7 C23 121.06(16) . . ?
C6 C7 C23 121.58(16) . . ?
C7 C8 C9 122.25(16) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C4 C9 C8 118.44(15) . . ?
C4 C9 C10 117.19(14) . . ?
C8 C9 C10 124.09(15) . . ?
C2 C10 C9 119.41(15) . . ?
C2 C10 C11 117.81(15) . . ?
C9 C10 C11 122.64(15) . . ?
C10 C11 C12 109.11(15) . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N1 C12 C11 111.14(15) . . ?
N1 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
N1 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C3 131.47(16) . . ?
C14 C13 S1 110.47(13) . . ?
C3 C13 S1 117.76(12) . . ?
C13 C14 C15 112.69(17) . . ?
C13 C14 H14 123.7 . . ?
C15 C14 H14 123.7 . . ?
C16 C15 C14 112.71(17) . . ?
C16 C15 H15 123.6 . . ?
C14 C15 H15 123.6 . . ?
C15 C16 S1 112.03(14) . . ?
C15 C16 H16 124.0 . . ?
S1 C16 H16 124.0 . . ?
C22 C17 C18 119.17(16) . . ?
C22 C17 C1 120.62(15) . . ?
C18 C17 C1 119.88(15) . . ?
C19 C18 C17 120.17(18) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.23(18) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.91(18) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.24(19) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.26(17) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C7 C23 H23A 109.5 . . ?
C7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C12 115.83(14) . . ?
C3 N2 C4 118.98(14) . . ?
C16 S1 C13 92.07(9) . . ?

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
N1 C1 C2 C10 -29.2(2) . . . . ?
C17 C1 C2 C10 141.33(15) . . . . ?
N1 C1 C2 C3 156.24(16) . . . . ?
C17 C1 C2 C3 -33.2(2) . . . . ?
C10 C2 C3 N2 -15.2(2) . . . . ?
C1 C2 C3 N2 159.26(15) . . . . ?
C10 C2 C3 C13 161.09(15) . . . . ?
C1 C2 C3 C13 -24.5(2) . . . . ?
N2 C4 C5 C6 -178.60(15) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C7 3.5(3) . . . . ?
C4 C5 C6 Cl1 -176.60(12) . . . . ?
C5 C6 C7 C8 -3.1(3) . . . . ?
Cl1 C6 C7 C8 177.01(13) . . . . ?
C5 C6 C7 C23 177.09(17) . . . . ?
Cl1 C6 C7 C23 -2.8(2) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C23 C7 C8 C9 178.63(17) . . . . ?
N2 C4 C9 C8 174.58(15) . . . . ?
C5 C4 C9 C8 -4.3(2) . . . . ?
N2 C4 C9 C10 -11.3(2) . . . . ?
C5 C4 C9 C10 169.81(14) . . . . ?
C7 C8 C9 C4 4.8(3) . . . . ?
C7 C8 C9 C10 -168.87(16) . . . . ?
C3 C2 C10 C9 11.8(2) . . . . ?
C1 C2 C10 C9 -163.23(14) . . . . ?
C3 C2 C10 C11 -172.32(15) . . . . ?
C1 C2 C10 C11 12.7(2) . . . . ?
C4 C9 C10 C2 0.6(2) . . . . ?
C8 C9 C10 C2 174.34(16) . . . . ?
C4 C9 C10 C11 -175.14(16) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C2 C10 C11 C12 27.3(2) . . . . ?
C9 C10 C11 C12 -156.90(16) . . . . ?
C10 C11 C12 N1 -56.4(2) . . . . ?
N2 C3 C13 C14 160.05(17) . . . . ?
C2 C3 C13 C14 -16.5(3) . . . . ?
N2 C3 C13 S1 -12.97(19) . . . . ?
C2 C3 C13 S1 170.50(12) . . . . ?
C3 C13 C14 C15 -174.31(17) . . . . ?
S1 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C15 C16 S1 1.2(2) . . . . ?
N1 C1 C17 C22 134.75(17) . . . . ?
C2 C1 C17 C22 -36.4(2) . . . . ?
N1 C1 C17 C18 -38.6(2) . . . . ?
C2 C1 C17 C18 150.29(15) . . . . ?
C22 C17 C18 C19 0.7(2) . . . . ?
C1 C17 C18 C19 174.14(15) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C21 C22 C17 -1.2(3) . . . . ?
C18 C17 C22 C21 0.5(2) . . . . ?
C1 C17 C22 C21 -172.91(16) . . . . ?
C17 C1 N1 C12 -172.22(14) . . . . ?
C2 C1 N1 C12 -1.3(2) . . . . ?
C11 C12 N1 C1 44.3(2) . . . . ?
C2 C3 N2 C4 4.9(2) . . . . ?
C13 C3 N2 C4 -171.67(14) . . . . ?
C9 C4 N2 C3 8.5(2) . . . . ?
C5 C4 N2 C3 -172.56(14) . . . . ?
C15 C16 S1 C13 -1.47(16) . . . . ?
C14 C13 S1 C16 1.34(14) . . . . ?
C3 C13 S1 C16 175.77(13) . . . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.059

