# 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_161122a
_database_code_depnum_ccdc_archive 'CCDC 1557713'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 Cl N O2 S'
_chemical_formula_weight         313.74

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   3.8280(2)
_cell_length_b                   13.3111(11)
_cell_length_c                   25.038(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.9190(10)
_cell_angle_gamma                90.00
_cell_volume                     1275.64(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    749
_cell_measurement_theta_min      2.234
_cell_measurement_theta_max      26.092

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8730
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6131
_diffrn_reflns_av_R_equivalents  0.1893
_diffrn_reflns_av_sigmaI/netI    0.1766
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2219
_reflns_number_gt                1119
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0805P)²+0.0000P] 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         2219
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1888
_refine_ls_R_factor_gt           0.1126
_refine_ls_wR_factor_ref         0.2492
_refine_ls_wR_factor_gt          0.2226
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.7740(7) 0.77643(16) 0.31198(8) 0.0541(7) Uani 1 1 d . . .
N1 N 0.2690(19) 0.6087(4) 0.0117(3) 0.0434(18) Uani 1 1 d . . .
H1 H 0.2017 0.5801 -0.0175 0.052 Uiso 1 1 calc R . .
O1 O 0.7203(18) 0.7548(4) 0.1910(2) 0.0583(19) Uani 1 1 d . . .
O2 O 0.0988(17) 0.4886(4) 0.0716(2) 0.0567(17) Uani 1 1 d . . .
S1 S 0.2330(6) 0.50410(14) 0.17633(8) 0.0418(6) Uani 1 1 d . . .
C1 C 0.407(2) 0.6160(5) 0.1526(3) 0.0349(19) Uani 1 1 d . . .
C2 C 0.561(2) 0.6778(6) 0.1979(3) 0.0359(19) Uani 1 1 d . . .
C3 C 0.509(2) 0.6282(6) 0.2487(3) 0.0368(19) Uani 1 1 d . . .
C4 C 0.340(2) 0.5346(5) 0.2420(3) 0.040(2) Uani 1 1 d . . .
C5 C 0.272(2) 0.4725(6) 0.2860(3) 0.047(2) Uani 1 1 d . . .
H5 H 0.1744 0.4092 0.2812 0.056 Uiso 1 1 calc R . .
C6 C 0.353(2) 0.5069(6) 0.3358(3) 0.052(2) Uani 1 1 d . . .
H6 H 0.3030 0.4674 0.3653 0.062 Uiso 1 1 calc R . .
C7 C 0.510(2) 0.6004(6) 0.3434(3) 0.042(2) Uani 1 1 d . . .
H7 H 0.5610 0.6223 0.3779 0.050 Uiso 1 1 calc R . .
C8 C 0.590(2) 0.6608(6) 0.3008(3) 0.042(2) Uani 1 1 d . . .
C9 C 0.238(2) 0.5690(6) 0.0607(3) 0.038(2) Uani 1 1 d . . .
C10 C 0.401(2) 0.6408(5) 0.1005(3) 0.0326(18) Uani 1 1 d . . .
C11 C 0.516(2) 0.7239(5) 0.0679(3) 0.038(2) Uani 1 1 d . . .
C12 C 0.427(2) 0.7035(5) 0.0149(3) 0.036(2) Uani 1 1 d . . .
C13 C 0.495(2) 0.7674(6) -0.0265(3) 0.046(2) Uani 1 1 d . . .
H13 H 0.4407 0.7499 -0.0616 0.055 Uiso 1 1 calc R . .
C14 C 0.646(3) 0.8578(6) -0.0143(4) 0.056(3) Uani 1 1 d . . .
H14 H 0.6981 0.9025 -0.0416 0.067 Uiso 1 1 calc R . .
C15 C 0.720(2) 0.8829(6) 0.0370(4) 0.050(2) Uani 1 1 d . . .
H15 H 0.8119 0.9463 0.0441 0.060 Uiso 1 1 calc R . .
C16 C 0.666(2) 0.8182(6) 0.0794(3) 0.043(2) Uani 1 1 d . . .
H16 H 0.7254 0.8365 0.1142 0.052 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 C8 1.714(8) . ?
N1 C9 1.343(9) . ?
N1 C12 1.401(9) . ?
N1 H1 0.8600 . ?
O1 C2 1.206(8) . ?
O2 C9 1.229(9) . ?
S1 C4 1.737(8) . ?
S1 C1 1.740(8) . ?
C1 C10 1.345(10) . ?
C1 C2 1.514(10) . ?
C2 C3 1.448(11) . ?
C3 C8 1.405(11) . ?
C3 C4 1.413(11) . ?
C4 C5 1.405(10) . ?
C5 C6 1.358(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(11) . ?
C7 H7 0.9300 . ?
C9 C10 1.511(10) . ?
C10 C11 1.448(10) . ?
C11 C12 1.393(10) . ?
C11 C16 1.406(10) . ?
C12 C13 1.368(11) . ?
C13 C14 1.367(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.354(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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 N1 C12 110.3(6) . . ?
C9 N1 H1 124.8 . . ?
C12 N1 H1 124.8 . . ?
C4 S1 C1 92.2(4) . . ?
C10 C1 C2 126.4(7) . . ?
C10 C1 S1 122.8(6) . . ?
C2 C1 S1 110.8(5) . . ?
O1 C2 C3 126.1(7) . . ?
O1 C2 C1 123.1(7) . . ?
C3 C2 C1 110.7(7) . . ?
C8 C3 C4 118.4(7) . . ?
C8 C3 C2 130.0(7) . . ?
C4 C3 C2 111.6(7) . . ?
C5 C4 C3 121.1(8) . . ?
C5 C4 S1 124.2(6) . . ?
C3 C4 S1 114.7(6) . . ?
C6 C5 C4 118.6(8) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 121.1(7) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 121.2(8) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C3 119.4(7) . . ?
C7 C8 Cl1 119.7(6) . . ?
C3 C8 Cl1 120.8(6) . . ?
O2 C9 N1 126.3(7) . . ?
O2 C9 C10 125.5(7) . . ?
N1 C9 C10 108.2(7) . . ?
C1 C10 C11 137.2(7) . . ?
C1 C10 C9 119.0(7) . . ?
C11 C10 C9 103.7(6) . . ?
C12 C11 C16 117.4(7) . . ?
C12 C11 C10 108.4(6) . . ?
C16 C11 C10 133.9(7) . . ?
C13 C12 C11 123.7(7) . . ?
C13 C12 N1 127.1(7) . . ?
C11 C12 N1 109.2(6) . . ?
C14 C13 C12 117.6(8) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C15 C14 C13 120.7(8) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 122.8(8) . . ?
C14 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C11 117.7(8) . . ?
C15 C16 H16 121.1 . . ?
C11 C16 H16 121.1 . . ?

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
C4 S1 C1 C10 -179.0(7) . . . . ?
C4 S1 C1 C2 1.3(6) . . . . ?
C10 C1 C2 O1 -5.4(13) . . . . ?
S1 C1 C2 O1 174.2(7) . . . . ?
C10 C1 C2 C3 178.2(8) . . . . ?
S1 C1 C2 C3 -2.1(8) . . . . ?
O1 C2 C3 C8 8.0(14) . . . . ?
C1 C2 C3 C8 -175.8(8) . . . . ?
O1 C2 C3 C4 -174.2(8) . . . . ?
C1 C2 C3 C4 2.0(9) . . . . ?
C8 C3 C4 C5 -3.7(12) . . . . ?
C2 C3 C4 C5 178.2(7) . . . . ?
C8 C3 C4 S1 177.1(6) . . . . ?
C2 C3 C4 S1 -1.0(9) . . . . ?
C1 S1 C4 C5 -179.4(7) . . . . ?
C1 S1 C4 C3 -0.2(7) . . . . ?
C3 C4 C5 C6 4.0(12) . . . . ?
S1 C4 C5 C6 -176.8(7) . . . . ?
C4 C5 C6 C7 -2.0(13) . . . . ?
C5 C6 C7 C8 -0.4(14) . . . . ?
C6 C7 C8 C3 0.8(12) . . . . ?
C6 C7 C8 Cl1 178.5(7) . . . . ?
C4 C3 C8 C7 1.2(12) . . . . ?
C2 C3 C8 C7 178.9(8) . . . . ?
C4 C3 C8 Cl1 -176.5(6) . . . . ?
C2 C3 C8 Cl1 1.2(12) . . . . ?
C12 N1 C9 O2 177.1(8) . . . . ?
C12 N1 C9 C10 -2.4(9) . . . . ?
C2 C1 C10 C11 -0.3(15) . . . . ?
S1 C1 C10 C11 -180.0(7) . . . . ?
C2 C1 C10 C9 179.5(7) . . . . ?
S1 C1 C10 C9 -0.1(10) . . . . ?
O2 C9 C10 C1 1.7(12) . . . . ?
N1 C9 C10 C1 -178.8(7) . . . . ?
O2 C9 C10 C11 -178.4(8) . . . . ?
N1 C9 C10 C11 1.1(8) . . . . ?
C1 C10 C11 C12 -179.6(9) . . . . ?
C9 C10 C11 C12 0.6(8) . . . . ?
C1 C10 C11 C16 -5.3(16) . . . . ?
C9 C10 C11 C16 174.8(9) . . . . ?
C16 C11 C12 C13 4.0(12) . . . . ?
C10 C11 C12 C13 179.3(7) . . . . ?
C16 C11 C12 N1 -177.4(7) . . . . ?
C10 C11 C12 N1 -2.0(9) . . . . ?
C9 N1 C12 C13 -178.6(8) . . . . ?
C9 N1 C12 C11 2.8(9) . . . . ?
C11 C12 C13 C14 -2.9(13) . . . . ?
N1 C12 C13 C14 178.7(8) . . . . ?
C12 C13 C14 C15 -0.8(14) . . . . ?
C13 C14 C15 C16 3.2(15) . . . . ?
C14 C15 C16 C11 -2.0(13) . . . . ?
C12 C11 C16 C15 -1.5(12) . . . . ?
C10 C11 C16 C15 -175.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.122
