# Electronic Supplementary Material (ESI) for ChemComm.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1526012'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 Cl N O2 S'
_chemical_formula_sum            'C24 H18 Cl N O2 S'
_chemical_formula_weight         419.90

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5389(3)
_cell_length_b                   10.7066(3)
_cell_length_c                   11.2370(3)
_cell_angle_alpha                66.5410(10)
_cell_angle_beta                 73.749(2)
_cell_angle_gamma                85.725(2)
_cell_volume                     1009.82(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7547
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      27.65

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .922
_exptl_absorpt_correction_T_max  .965


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  APEXII
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            34179
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.65
_reflns_number_total             4662
_reflns_number_gt                3340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens 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)+(0.0710P)²+0.4916P] 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         4662
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0857
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.06615(9) 1.08339(7) 0.28612(8) 0.0666(2) Uani 1 1 d . . .
S1 S 0.42194(9) 0.81467(8) 0.00612(6) 0.0618(2) Uani 1 1 d . . .
O2 O 0.1159(2) 0.38188(18) 0.70205(17) 0.0541(5) Uani 1 1 d . . .
O1 O 0.0116(2) 0.5812(2) 0.67515(18) 0.0612(5) Uani 1 1 d . . .
N1 N 0.35597(19) 0.57940(18) 0.29569(18) 0.0369(4) Uani 1 1 d . . .
C8 C 0.2960(2) 0.7059(2) 0.2773(2) 0.0373(5) Uani 1 1 d . . .
C13 C 0.1985(2) 0.7013(2) 0.3980(2) 0.0384(5) Uani 1 1 d . . .
C15 C 0.2936(2) 0.4914(2) 0.4296(2) 0.0359(5) Uani 1 1 d . . .
C19 C 0.3240(2) 0.3445(2) 0.4846(2) 0.0366(5) Uani 1 1 d . . .
C14 C 0.1970(2) 0.5631(2) 0.4933(2) 0.0369(5) Uani 1 1 d . . .
C6 C 0.4818(2) 0.5638(2) 0.1969(2) 0.0393(5) Uani 1 1 d . . .
C16 C 0.0988(2) 0.5123(2) 0.6308(2) 0.0395(5) Uani 1 1 d . . .
C9 C 0.3201(2) 0.8232(2) 0.1583(2) 0.0418(5) Uani 1 1 d . . .
C7 C 0.5731(2) 0.4558(3) 0.2291(2) 0.0433(5) Uani 1 1 d . . .
H7A H 0.5531 0.3919 0.3177 0.052 Uiso 1 1 calc R . .
C12 C 0.1250(3) 0.8185(2) 0.4029(2) 0.0446(6) Uani 1 1 d . . .
H12A H 0.0591 0.8178 0.4818 0.054 Uiso 1 1 calc R . .
C10 C 0.2501(3) 0.9390(2) 0.1644(2) 0.0472(6) Uani 1 1 d . . .
H10A H 0.2665 1.0199 0.0879 0.057 Uiso 1 1 calc R . .
C24 C 0.2730(3) 0.2553(3) 0.4434(3) 0.0479(6) Uani 1 1 d . . .
H24A H 0.2226 0.2875 0.3778 0.058 Uiso 1 1 calc R . .
C5 C 0.5171(3) 0.6641(3) 0.0649(2) 0.0457(6) Uani 1 1 d . . .
C2 C 0.6938(3) 0.4396(3) 0.1334(3) 0.0503(6) Uani 1 1 d . . .
C11 C 0.1546(3) 0.9340(2) 0.2861(3) 0.0471(6) Uani 1 1 d . . .
C20 C 0.4006(3) 0.2936(3) 0.5818(3) 0.0492(6) Uani 1 1 d . . .
H20A H 0.4348 0.3526 0.6107 0.059 Uiso 1 1 calc R . .
C17 C 0.0272(3) 0.3241(3) 0.8405(2) 0.0549(7) Uani 1 1 d . . .
H17A H -0.0755 0.3236 0.8440 0.066 Uiso 1 1 calc R . .
H17B H 0.0418 0.3770 0.8893 0.066 Uiso 1 1 calc R . .
C4 C 0.6378(3) 0.6476(3) -0.0302(3) 0.0584(7) Uani 1 1 d . . .
H4A H 0.6611 0.7133 -0.1179 0.070 Uiso 1 1 calc R . .
C3 C 0.7235(3) 0.5369(3) 0.0020(3) 0.0596(7) Uani 1 1 d . . .
H3A H 0.8018 0.5270 -0.0644 0.072 Uiso 1 1 calc R . .
C21 C 0.4262(3) 0.1570(3) 0.6356(3) 0.0636(8) Uani 1 1 d . . .
H21A H 0.4792 0.1242 0.6991 0.076 Uiso 1 1 calc R . .
C23 C 0.2974(3) 0.1177(3) 0.5004(4) 0.0669(8) Uani 1 1 d . . .
H23A H 0.2616 0.0574 0.4738 0.080 Uiso 1 1 calc R . .
C1 C 0.7879(3) 0.3187(3) 0.1737(3) 0.0643(8) Uani 1 1 d . . .
H1A H 0.8662 0.3229 0.0966 0.097 Uiso 1 1 calc R . .
H1B H 0.7297 0.2361 0.2071 0.097 Uiso 1 1 calc R . .
H1C H 0.8275 0.3199 0.2429 0.097 Uiso 1 1 calc R . .
C22 C 0.3736(3) 0.0693(3) 0.5954(4) 0.0690(9) Uani 1 1 d . . .
H22A H 0.3897 -0.0233 0.6326 0.083 Uiso 1 1 calc R . .
C18 C 0.0746(4) 0.1824(3) 0.9009(3) 0.0855(11) Uani 1 1 d . . .
H18A H 0.0190 0.1403 0.9936 0.128 Uiso 1 1 calc R . .
H18B H 0.1766 0.1845 0.8959 0.128 Uiso 1 1 calc R . .
H18C H 0.0587 0.1312 0.8522 0.128 Uiso 1 1 calc R . .


_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 C11 1.752(2) . ?
S1 C9 1.749(2) . ?
S1 C5 1.769(3) . ?
O2 C16 1.329(3) . ?
O2 C17 1.447(3) . ?
O1 C16 1.206(3) . ?
N1 C8 1.390(3) . ?
N1 C15 1.399(3) . ?
N1 C6 1.440(3) . ?
C8 C9 1.397(3) . ?
C8 C13 1.398(3) . ?
C13 C12 1.403(3) . ?
C13 C14 1.439(3) . ?
C15 C14 1.383(3) . ?
C15 C19 1.483(3) . ?
C19 C24 1.382(3) . ?
C19 C20 1.392(3) . ?
C14 C16 1.469(3) . ?
C6 C7 1.386(3) . ?
C6 C5 1.404(3) . ?
C9 C10 1.381(3) . ?
C7 C2 1.392(3) . ?
C7 H7A 0.9300 . ?
C12 C11 1.373(3) . ?
C12 H12A 0.9300 . ?
C10 C11 1.398(4) . ?
C10 H10A 0.9300 . ?
C24 C23 1.384(4) . ?
C24 H24A 0.9300 . ?
C5 C4 1.389(4) . ?
C2 C3 1.390(4) . ?
C2 C1 1.508(4) . ?
C20 C21 1.375(4) . ?
C20 H20A 0.9300 . ?
C17 C18 1.489(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C4 C3 1.372(4) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C21 C22 1.368(4) . ?
C21 H21A 0.9300 . ?
C23 C22 1.369(4) . ?
C23 H23A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C22 H22A 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C9 S1 C5 101.09(11) . . ?
C16 O2 C17 116.9(2) . . ?
C8 N1 C15 107.47(18) . . ?
C8 N1 C6 121.02(18) . . ?
C15 N1 C6 130.09(19) . . ?
N1 C8 C9 127.8(2) . . ?
N1 C8 C13 110.02(19) . . ?
C9 C8 C13 122.1(2) . . ?
C8 C13 C12 119.8(2) . . ?
C8 C13 C14 105.49(19) . . ?
C12 C13 C14 134.6(2) . . ?
C14 C15 N1 108.58(19) . . ?
C14 C15 C19 128.2(2) . . ?
N1 C15 C19 123.1(2) . . ?
C24 C19 C20 119.0(2) . . ?
C24 C19 C15 120.7(2) . . ?
C20 C19 C15 120.3(2) . . ?
C15 C14 C13 108.40(19) . . ?
C15 C14 C16 128.6(2) . . ?
C13 C14 C16 122.9(2) . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 N1 122.1(2) . . ?
C5 C6 N1 119.2(2) . . ?
O1 C16 O2 123.2(2) . . ?
O1 C16 C14 123.8(2) . . ?
O2 C16 C14 113.0(2) . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 S1 122.36(18) . . ?
C8 C9 S1 119.57(19) . . ?
C6 C7 C2 122.2(2) . . ?
C6 C7 H7A 118.9 . . ?
C2 C7 H7A 118.9 . . ?
C11 C12 C13 117.1(2) . . ?
C11 C12 H12A 121.5 . . ?
C13 C12 H12A 121.5 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C23 C24 C19 119.6(2) . . ?
C23 C24 H24A 120.2 . . ?
C19 C24 H24A 120.2 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 S1 115.4(2) . . ?
C6 C5 S1 125.77(19) . . ?
C3 C2 C7 118.2(3) . . ?
C3 C2 C1 121.9(2) . . ?
C7 C2 C1 119.9(3) . . ?
C12 C11 C10 123.5(2) . . ?
C12 C11 Cl1 119.1(2) . . ?
C10 C11 Cl1 117.39(18) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
O2 C17 C18 106.6(2) . . ?
O2 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O2 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23A 119.6 . . ?
C24 C23 H23A 119.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22A 119.9 . . ?
C23 C22 H22A 119.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C15 N1 C8 C9 -176.6(2) . . . . ?
C6 N1 C8 C9 15.7(3) . . . . ?
C15 N1 C8 C13 1.2(2) . . . . ?
C6 N1 C8 C13 -166.44(19) . . . . ?
N1 C8 C13 C12 179.88(19) . . . . ?
C9 C8 C13 C12 -2.1(3) . . . . ?
N1 C8 C13 C14 -1.6(2) . . . . ?
C9 C8 C13 C14 176.4(2) . . . . ?
C8 N1 C15 C14 -0.4(2) . . . . ?
C6 N1 C15 C14 165.8(2) . . . . ?
C8 N1 C15 C19 175.98(19) . . . . ?
C6 N1 C15 C19 -17.8(3) . . . . ?
C14 C15 C19 C24 106.5(3) . . . . ?
N1 C15 C19 C24 -69.1(3) . . . . ?
C14 C15 C19 C20 -71.5(3) . . . . ?
N1 C15 C19 C20 112.8(3) . . . . ?
N1 C15 C14 C13 -0.6(2) . . . . ?
C19 C15 C14 C13 -176.7(2) . . . . ?
N1 C15 C14 C16 175.5(2) . . . . ?
C19 C15 C14 C16 -0.6(4) . . . . ?
C8 C13 C14 C15 1.3(2) . . . . ?
C12 C13 C14 C15 179.5(2) . . . . ?
C8 C13 C14 C16 -175.0(2) . . . . ?
C12 C13 C14 C16 3.2(4) . . . . ?
C8 N1 C6 C7 157.6(2) . . . . ?
C15 N1 C6 C7 -7.0(3) . . . . ?
C8 N1 C6 C5 -19.6(3) . . . . ?
C15 N1 C6 C5 175.8(2) . . . . ?
C17 O2 C16 O1 -2.1(4) . . . . ?
C17 O2 C16 C14 177.9(2) . . . . ?
C15 C14 C16 O1 -175.3(2) . . . . ?
C13 C14 C16 O1 0.2(4) . . . . ?
C15 C14 C16 O2 4.7(3) . . . . ?
C13 C14 C16 O2 -179.8(2) . . . . ?
N1 C8 C9 C10 -178.9(2) . . . . ?
C13 C8 C9 C10 3.5(3) . . . . ?
N1 C8 C9 S1 7.1(3) . . . . ?
C13 C8 C9 S1 -170.48(17) . . . . ?
C5 S1 C9 C10 166.5(2) . . . . ?
C5 S1 C9 C8 -19.8(2) . . . . ?
C5 C6 C7 C2 -3.6(3) . . . . ?
N1 C6 C7 C2 179.2(2) . . . . ?
C8 C13 C12 C11 -0.4(3) . . . . ?
C14 C13 C12 C11 -178.5(2) . . . . ?
C8 C9 C10 C11 -2.4(3) . . . . ?
S1 C9 C10 C11 171.42(19) . . . . ?
C20 C19 C24 C23 0.8(4) . . . . ?
C15 C19 C24 C23 -177.3(2) . . . . ?
C7 C6 C5 C4 3.3(4) . . . . ?
N1 C6 C5 C4 -179.4(2) . . . . ?
C7 C6 C5 S1 -175.89(18) . . . . ?
N1 C6 C5 S1 1.4(3) . . . . ?
C9 S1 C5 C4 -162.9(2) . . . . ?
C9 S1 C5 C6 16.3(2) . . . . ?
C6 C7 C2 C3 0.9(4) . . . . ?
C6 C7 C2 C1 -178.9(2) . . . . ?
C13 C12 C11 C10 1.5(4) . . . . ?
C13 C12 C11 Cl1 180.00(18) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C10 C11 Cl1 -178.59(18) . . . . ?
C24 C19 C20 C21 0.4(4) . . . . ?
C15 C19 C20 C21 178.5(2) . . . . ?
C16 O2 C17 C18 -175.6(3) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
S1 C5 C4 C3 178.7(2) . . . . ?
C5 C4 C3 C2 -2.1(4) . . . . ?
C7 C2 C3 C4 1.9(4) . . . . ?
C1 C2 C3 C4 -178.2(3) . . . . ?
C19 C20 C21 C22 -1.3(4) . . . . ?
C19 C24 C23 C22 -1.2(5) . . . . ?
C20 C21 C22 C23 0.9(5) . . . . ?
C24 C23 C22 C21 0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.057


