# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_cd16579
_database_code_depnum_ccdc_archive 'CCDC 1561030'
_audit_update_record             
;
2017-07-08 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cl N O4 S'
_chemical_formula_weight         377.83

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.1621(6)
_cell_length_b                   16.3247(18)
_cell_length_c                   20.251(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1706.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3483
_cell_measurement_theta_min      4.734
_cell_measurement_theta_max      51.798

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.370
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10224
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.602
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3354
_reflns_number_gt                3016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.3361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3354
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.41600(16) 0.40223(5) 0.76076(4) 0.0459(2) Uani 1 1 d . . . . .
Cl1 Cl 0.8920(3) 0.67265(8) 1.03809(7) 0.1013(5) Uani 1 1 d . . . . .
N1 N 0.6276(7) 0.29735(17) 0.92612(15) 0.0505(8) Uani 1 1 d . . . . .
O1 O 0.2070(5) 0.44893(16) 0.78862(14) 0.0609(7) Uani 1 1 d . . . . .
O2 O 0.5713(6) 0.44158(18) 0.71158(13) 0.0668(7) Uani 1 1 d . . . . .
O3 O 0.9296(11) 0.1628(3) 0.9410(2) 0.156(3) Uani 1 1 d . . . . .
O4 O 0.7868(6) 0.10425(17) 0.85410(15) 0.0747(9) Uani 1 1 d . . . . .
C1 C 0.4271(7) 0.2431(2) 0.76186(15) 0.0443(7) Uani 1 1 d . . . . .
C2 C 0.3580(7) 0.1638(2) 0.74422(17) 0.0563(9) Uani 1 1 d . . . . .
H2 H 0.4400 0.1190 0.7635 0.068 Uiso 1 1 calc R U . . .
C3 C 0.1648(9) 0.1521(3) 0.6973(2) 0.0675(12) Uani 1 1 d . . . . .
H3 H 0.1158 0.0992 0.6858 0.081 Uiso 1 1 calc R U . . .
C4 C 0.0451(9) 0.2180(3) 0.66771(18) 0.0657(11) Uani 1 1 d . . . . .
H4 H -0.0818 0.2088 0.6360 0.079 Uiso 1 1 calc R U . . .
C5 C 0.1100(8) 0.2970(2) 0.68423(17) 0.0549(9) Uani 1 1 d . . . . .
H5 H 0.0289 0.3416 0.6645 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3020(7) 0.3073(2) 0.73162(16) 0.0448(8) Uani 1 1 d . . . . .
C7 C 0.6223(6) 0.35979(19) 0.82368(15) 0.0405(7) Uani 1 1 d . . . . .
H7 H 0.7969 0.3828 0.8195 0.049 Uiso 1 1 calc R U . . .
C8 C 0.6321(6) 0.2662(2) 0.81171(15) 0.0406(7) Uani 1 1 d . . . . .
H8 H 0.8033 0.2510 0.7948 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5929(7) 0.22849(19) 0.88152(14) 0.0418(7) Uani 1 1 d . . . . .
H9 H 0.4165 0.2069 0.8856 0.050 Uiso 1 1 calc R U . . .
C10 C 0.5245(7) 0.37085(19) 0.89541(16) 0.0445(8) Uani 1 1 d . . . . .
H10 H 0.3347 0.3694 0.8962 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6201(7) 0.4474(2) 0.92965(16) 0.0467(8) Uani 1 1 d . . . . .
C12 C 0.4900(9) 0.5207(2) 0.9235(2) 0.0650(11) Uani 1 1 d . . . . .
H12 H 0.3434 0.5235 0.8969 0.078 Uiso 1 1 calc R U . . .
C13 C 0.5738(11) 0.5902(2) 0.9562(2) 0.0720(12) Uani 1 1 d . . . . .
H13 H 0.4853 0.6395 0.9513 0.086 Uiso 1 1 calc R U . . .
C14 C 0.7848(9) 0.5859(2) 0.9951(2) 0.0634(11) Uani 1 1 d . . . . .
C15 C 0.9190(10) 0.5148(3) 1.0024(2) 0.0715(11) Uani 1 1 d . . . . .
H15 H 1.0646 0.5128 1.0294 0.086 Uiso 1 1 calc R U . . .
C16 C 0.8362(8) 0.4452(3) 0.9691(2) 0.0631(10) Uani 1 1 d . . . . .
H16 H 0.9283 0.3966 0.9736 0.076 Uiso 1 1 calc R U . . .
C17 C 0.7863(8) 0.1622(2) 0.89686(16) 0.0499(8) Uani 1 1 d . . . . .
C18 C 0.9694(10) 0.0381(3) 0.8622(2) 0.0720(12) Uani 1 1 d . . . . .
H18A H 1.1332 0.0598 0.8763 0.108 Uiso 1 1 calc R U . . .
H18B H 0.9907 0.0099 0.8210 0.108 Uiso 1 1 calc R U . . .
H18C H 0.9057 0.0005 0.8949 0.108 Uiso 1 1 calc R U . . .
H1 H 0.570(8) 0.289(2) 0.9637(18) 0.053(11) Uiso 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
S1 O2 1.431(3) . ?
S1 O1 1.436(3) . ?
S1 C6 1.759(3) . ?
S1 C7 1.800(3) . ?
Cl1 C14 1.752(4) . ?
N1 C10 1.453(4) . ?
N1 C9 1.453(4) . ?
N1 H1 0.83(4) . ?
O3 C17 1.160(5) . ?
O4 C17 1.282(4) . ?
O4 C18 1.443(5) . ?
C1 C6 1.375(5) . ?
C1 C2 1.390(5) . ?
C1 C8 1.511(5) . ?
C2 C3 1.390(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.547(4) . ?
C7 C10 1.548(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.555(4) . ?
C8 H8 0.9800 . ?
C9 C17 1.505(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.512(5) . ?
C10 H10 0.9800 . ?
C11 C16 1.373(6) . ?
C11 C12 1.378(5) . ?
C12 C13 1.384(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.346(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(6) . ?
C15 C16 1.389(6) . ?
C15 H15 0.9300 . ?
C16 H16 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
O2 S1 O1 117.13(18) . . ?
O2 S1 C6 110.45(17) . . ?
O1 S1 C6 110.36(16) . . ?
O2 S1 C7 109.52(16) . . ?
O1 S1 C7 111.75(15) . . ?
C6 S1 C7 95.53(15) . . ?
C10 N1 C9 109.1(3) . . ?
C10 N1 H1 114(3) . . ?
C9 N1 H1 113(3) . . ?
C17 O4 C18 118.4(3) . . ?
C6 C1 C2 118.4(3) . . ?
C6 C1 C8 115.8(3) . . ?
C2 C1 C8 125.8(3) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 117.2(4) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C1 C6 C5 123.3(3) . . ?
C1 C6 S1 111.4(2) . . ?
C5 C6 S1 125.3(3) . . ?
C8 C7 C10 105.8(2) . . ?
C8 C7 S1 106.8(2) . . ?
C10 C7 S1 115.2(2) . . ?
C8 C7 H7 109.6 . . ?
C10 C7 H7 109.6 . . ?
S1 C7 H7 109.6 . . ?
C1 C8 C7 109.2(3) . . ?
C1 C8 C9 114.7(3) . . ?
C7 C8 C9 104.1(2) . . ?
C1 C8 H8 109.6 . . ?
C7 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
N1 C9 C17 110.2(3) . . ?
N1 C9 C8 104.0(3) . . ?
C17 C9 C8 112.7(3) . . ?
N1 C9 H9 109.9 . . ?
C17 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
N1 C10 C11 111.5(3) . . ?
N1 C10 C7 100.7(2) . . ?
C11 C10 C7 114.8(3) . . ?
N1 C10 H10 109.8 . . ?
C11 C10 H10 109.8 . . ?
C7 C10 H10 109.8 . . ?
C16 C11 C12 118.1(4) . . ?
C16 C11 C10 120.7(3) . . ?
C12 C11 C10 121.1(3) . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 Cl1 120.3(4) . . ?
C15 C14 Cl1 118.4(4) . . ?
C14 C15 C16 119.2(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 120.8(4) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
O3 C17 O4 121.7(4) . . ?
O3 C17 C9 125.2(3) . . ?
O4 C17 C9 113.1(3) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 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
C6 C1 C2 C3 -0.5(5) . . . . ?
C8 C1 C2 C3 -180.0(3) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C8 C1 C6 C5 179.5(3) . . . . ?
C2 C1 C6 S1 179.8(3) . . . . ?
C8 C1 C6 S1 -0.6(4) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C4 C5 C6 S1 -179.8(3) . . . . ?
O2 S1 C6 C1 107.5(3) . . . . ?
O1 S1 C6 C1 -121.4(3) . . . . ?
C7 S1 C6 C1 -5.8(3) . . . . ?
O2 S1 C6 C5 -72.7(3) . . . . ?
O1 S1 C6 C5 58.4(4) . . . . ?
C7 S1 C6 C5 174.1(3) . . . . ?
O2 S1 C7 C8 -104.1(2) . . . . ?
O1 S1 C7 C8 124.4(2) . . . . ?
C6 S1 C7 C8 9.9(2) . . . . ?
O2 S1 C7 C10 138.7(2) . . . . ?
O1 S1 C7 C10 7.3(3) . . . . ?
C6 S1 C7 C10 -107.3(2) . . . . ?
C6 C1 C8 C7 8.2(4) . . . . ?
C2 C1 C8 C7 -172.4(3) . . . . ?
C6 C1 C8 C9 124.6(3) . . . . ?
C2 C1 C8 C9 -56.0(4) . . . . ?
C10 C7 C8 C1 111.8(3) . . . . ?
S1 C7 C8 C1 -11.4(3) . . . . ?
C10 C7 C8 C9 -11.1(3) . . . . ?
S1 C7 C8 C9 -134.3(2) . . . . ?
C10 N1 C9 C17 156.4(3) . . . . ?
C10 N1 C9 C8 35.3(4) . . . . ?
C1 C8 C9 N1 -132.4(3) . . . . ?
C7 C8 C9 N1 -13.1(4) . . . . ?
C1 C8 C9 C17 108.2(3) . . . . ?
C7 C8 C9 C17 -132.5(3) . . . . ?
C9 N1 C10 C11 -163.9(3) . . . . ?
C9 N1 C10 C7 -41.6(4) . . . . ?
C8 C7 C10 N1 30.9(3) . . . . ?
S1 C7 C10 N1 148.6(2) . . . . ?
C8 C7 C10 C11 150.9(3) . . . . ?
S1 C7 C10 C11 -91.4(3) . . . . ?
N1 C10 C11 C16 19.1(4) . . . . ?
C7 C10 C11 C16 -94.6(4) . . . . ?
N1 C10 C11 C12 -159.4(3) . . . . ?
C7 C10 C11 C12 86.9(4) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
C10 C11 C12 C13 178.3(4) . . . . ?
C11 C12 C13 C14 -0.6(7) . . . . ?
C12 C13 C14 C15 0.7(7) . . . . ?
C12 C13 C14 Cl1 -179.0(3) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
Cl1 C14 C15 C16 179.6(3) . . . . ?
C12 C11 C16 C15 0.8(6) . . . . ?
C10 C11 C16 C15 -177.7(4) . . . . ?
C14 C15 C16 C11 -0.6(7) . . . . ?
C18 O4 C17 O3 0.7(7) . . . . ?
C18 O4 C17 C9 178.2(4) . . . . ?
N1 C9 C17 O3 5.5(7) . . . . ?
C8 C9 C17 O3 121.3(5) . . . . ?
N1 C9 C17 O4 -171.9(3) . . . . ?
C8 C9 C17 O4 -56.1(4) . . . . ?

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4



