# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1mnskm
_database_code_depnum_ccdc_archive 'CCDC 1509531'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.cclet.2015.05.040 2015
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Cl2 N3 O4 S'
_chemical_formula_weight         402.24

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)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3908(12)
_cell_length_b                   8.3911(7)
_cell_length_c                   18.9319(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.049(2)
_cell_angle_gamma                90.00
_cell_volume                     1739.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5914
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_T_max  0.9403
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13757
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3004
_reflns_number_gt                2884
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.1200P)²+6.9197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     228
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.2049
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
S1 S 0.35727(10) 0.55695(13) 0.23357(6) 0.0238(3) Uani 1 1 d . . .
Cl1 Cl 0.58556(10) 0.35263(15) 0.12675(7) 0.0304(4) Uani 1 1 d . . .
Cl2 Cl 0.30414(11) 0.22454(14) 0.06313(6) 0.0292(4) Uani 1 1 d . . .
O1 O 0.1291(3) 0.5810(4) 0.23613(16) 0.0190(7) Uani 1 1 d . . .
O2 O 0.2332(3) 0.2846(4) 0.36777(19) 0.0273(8) Uani 1 1 d . . .
O3 O 0.3822(3) 0.4533(4) 0.42505(18) 0.0228(7) Uani 1 1 d . . .
O4 O 0.1298(3) 0.7741(3) 0.43944(17) 0.0203(7) Uani 1 1 d . . .
N1 N 0.4883(4) 0.5189(5) 0.2150(2) 0.0286(9) Uani 1 1 d . . .
N2 N 0.0653(3) 0.4803(4) 0.1800(2) 0.0199(8) Uani 1 1 d . . .
N3 N 0.2223(3) 0.6687(4) 0.43551(19) 0.0184(8) Uani 1 1 d . . .
C1 C 0.4687(4) 0.4147(6) 0.1612(2) 0.0238(10) Uani 1 1 d . . .
C2 C 0.3477(4) 0.3602(5) 0.1330(2) 0.0196(9) Uani 1 1 d . . .
C3 C 0.2712(4) 0.4309(5) 0.1679(2) 0.0198(9) Uani 1 1 d . . .
C4 C 0.1400(4) 0.4095(5) 0.1506(2) 0.0199(9) Uani 1 1 d . . .
H4 H 0.1052 0.3344 0.1131 0.024 Uiso 1 1 calc R . .
C5 C 0.0410(4) 0.6720(5) 0.2630(2) 0.0192(9) Uani 1 1 d . . .
H5A H -0.0211 0.7184 0.2207 0.023 Uiso 1 1 calc R . .
H5B H 0.0837 0.7609 0.2941 0.023 Uiso 1 1 calc R . .
C6 C -0.0217(4) 0.5698(5) 0.3071(2) 0.0159(9) Uani 1 1 d . . .
C7 C -0.1466(4) 0.5399(5) 0.2816(2) 0.0196(9) Uani 1 1 d . . .
H7 H -0.1922 0.5840 0.2360 0.024 Uiso 1 1 calc R . .
C8 C -0.2053(4) 0.4462(5) 0.3220(3) 0.0214(9) Uani 1 1 d . . .
H8 H -0.2908 0.4283 0.3047 0.026 Uiso 1 1 calc R . .
C9 C -0.1381(4) 0.3788(5) 0.3880(2) 0.0236(10) Uani 1 1 d . . .
H9 H -0.1778 0.3138 0.4154 0.028 Uiso 1 1 calc R . .
C10 C -0.0142(4) 0.4062(5) 0.4136(2) 0.0195(9) Uani 1 1 d . . .
H10 H 0.0314 0.3585 0.4583 0.023 Uiso 1 1 calc R . .
C11 C 0.0445(4) 0.5035(5) 0.3742(2) 0.0164(8) Uani 1 1 d . . .
C12 C 0.1771(4) 0.5376(5) 0.4038(2) 0.0164(9) Uani 1 1 d . . .
C13 C 0.2668(4) 0.4113(5) 0.3967(2) 0.0190(9) Uani 1 1 d . . .
C14 C 0.4718(4) 0.3335(6) 0.4200(3) 0.0289(11) Uani 1 1 d U . .
H14A H 0.4535 0.2332 0.4412 0.043 Uiso 1 1 calc R . .
H14B H 0.5536 0.3699 0.4470 0.043 Uiso 1 1 calc R . .
H14C H 0.4687 0.3166 0.3683 0.043 Uiso 1 1 calc R . .
C15 C 0.1835(4) 0.9265(5) 0.4651(3) 0.0253(10) Uani 1 1 d . . .
H15A H 0.2546 0.9106 0.5076 0.038 Uiso 1 1 calc R . .
H15B H 0.1232 0.9928 0.4796 0.038 Uiso 1 1 calc R . .
H15C H 0.2090 0.9795 0.4257 0.038 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
S1 N1 1.657(4) . ?
S1 C3 1.718(4) . ?
Cl1 C1 1.717(5) . ?
Cl2 C2 1.712(4) . ?
O1 N2 1.395(5) . ?
O1 C5 1.460(5) . ?
O2 C13 1.209(5) . ?
O3 C13 1.323(5) . ?
O3 C14 1.455(6) . ?
O4 N3 1.394(5) . ?
O4 C15 1.442(5) . ?
N1 C1 1.314(7) . ?
N2 C4 1.284(6) . ?
N3 C12 1.290(6) . ?
C1 C2 1.409(7) . ?
C2 C3 1.367(6) . ?
C3 C4 1.450(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.508(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.393(6) . ?
C6 C11 1.401(6) . ?
C7 C8 1.391(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.487(6) . ?
C12 C13 1.504(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 S1 C3 95.5(2) . . ?
N2 O1 C5 108.6(3) . . ?
C13 O3 C14 115.2(4) . . ?
N3 O4 C15 108.9(3) . . ?
C1 N1 S1 108.8(3) . . ?
C4 N2 O1 110.0(3) . . ?
C12 N3 O4 110.8(3) . . ?
N1 C1 C2 116.6(4) . . ?
N1 C1 Cl1 120.8(4) . . ?
C2 C1 Cl1 122.5(4) . . ?
C3 C2 C1 111.4(4) . . ?
C3 C2 Cl2 125.1(4) . . ?
C1 C2 Cl2 123.5(3) . . ?
C2 C3 C4 126.3(4) . . ?
C2 C3 S1 107.7(3) . . ?
C4 C3 S1 125.9(3) . . ?
N2 C4 C3 127.6(4) . . ?
N2 C4 H4 116.2 . . ?
C3 C4 H4 116.2 . . ?
O1 C5 C6 111.8(3) . . ?
O1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
O1 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C11 119.0(4) . . ?
C7 C6 C5 120.3(4) . . ?
C11 C6 C5 120.6(4) . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 119.7(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.3(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.0(4) . . ?
C10 C11 C12 119.9(4) . . ?
C6 C11 C12 120.1(4) . . ?
N3 C12 C11 125.0(4) . . ?
N3 C12 C13 116.7(4) . . ?
C11 C12 C13 118.4(4) . . ?
O2 C13 O3 125.0(4) . . ?
O2 C13 C12 121.5(4) . . ?
O3 C13 C12 113.5(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C3 S1 N1 C1 0.0(4) . . . . ?
C5 O1 N2 C4 174.0(3) . . . . ?
C15 O4 N3 C12 -171.7(4) . . . . ?
S1 N1 C1 C2 -0.5(5) . . . . ?
S1 N1 C1 Cl1 178.4(2) . . . . ?
N1 C1 C2 C3 0.8(6) . . . . ?
Cl1 C1 C2 C3 -178.0(3) . . . . ?
N1 C1 C2 Cl2 -179.9(3) . . . . ?
Cl1 C1 C2 Cl2 1.2(6) . . . . ?
C1 C2 C3 C4 176.5(4) . . . . ?
Cl2 C2 C3 C4 -2.7(6) . . . . ?
C1 C2 C3 S1 -0.8(4) . . . . ?
Cl2 C2 C3 S1 180.0(3) . . . . ?
N1 S1 C3 C2 0.5(3) . . . . ?
N1 S1 C3 C4 -176.8(4) . . . . ?
O1 N2 C4 C3 -2.7(6) . . . . ?
C2 C3 C4 N2 -176.2(4) . . . . ?
S1 C3 C4 N2 0.6(7) . . . . ?
N2 O1 C5 C6 72.2(4) . . . . ?
O1 C5 C6 C7 -114.4(4) . . . . ?
O1 C5 C6 C11 65.6(5) . . . . ?
C11 C6 C7 C8 0.2(6) . . . . ?
C5 C6 C7 C8 -179.8(4) . . . . ?
C6 C7 C8 C9 -1.3(6) . . . . ?
C7 C8 C9 C10 0.7(7) . . . . ?
C8 C9 C10 C11 1.0(7) . . . . ?
C9 C10 C11 C6 -2.1(6) . . . . ?
C9 C10 C11 C12 177.5(4) . . . . ?
C7 C6 C11 C10 1.5(6) . . . . ?
C5 C6 C11 C10 -178.5(4) . . . . ?
C7 C6 C11 C12 -178.1(4) . . . . ?
C5 C6 C11 C12 1.9(6) . . . . ?
O4 N3 C12 C11 0.9(5) . . . . ?
O4 N3 C12 C13 -179.2(3) . . . . ?
C10 C11 C12 N3 -102.5(5) . . . . ?
C6 C11 C12 N3 77.1(5) . . . . ?
C10 C11 C12 C13 77.6(5) . . . . ?
C6 C11 C12 C13 -102.8(5) . . . . ?
C14 O3 C13 O2 -0.3(6) . . . . ?
C14 O3 C13 C12 179.3(4) . . . . ?
N3 C12 C13 O2 -180.0(4) . . . . ?
C11 C12 C13 O2 0.0(6) . . . . ?
N3 C12 C13 O3 0.4(5) . . . . ?
C11 C12 C13 O3 -179.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.107
