# 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
_database_code_depnum_ccdc_archive 'CCDC 1505456'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2016-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Cl3 N O4 S'
_chemical_formula_sum            'C10 H10 Cl3 N O4 S'
_chemical_formula_weight         346.60

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.9570(6)
_cell_length_b                   9.0926(10)
_cell_length_c                   12.0788(12)
_cell_angle_alpha                110.282(9)
_cell_angle_beta                 100.464(7)
_cell_angle_gamma                96.922(8)
_cell_volume                     690.69(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    1883
_cell_measurement_theta_min      1.8477
_cell_measurement_theta_max      29.4230

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.821
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_number            5866
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.851
_diffrn_reflns_theta_max         26.367
_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             2829
_reflns_number_gt                2122
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0298P)²+0.0062P] 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     SHELXL
_refine_ls_extinction_coef       0.0033(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2829
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Cl2 Cl 0.26130(9) -0.06716(9) 1.02607(6) 0.02476(19) Uani 1 1 d . . . . .
S1 S -0.20515(9) -0.38963(8) 0.59132(6) 0.01867(18) Uani 1 1 d . . . . .
Cl1 Cl 0.38865(10) -0.32356(9) 0.85475(6) 0.02602(19) Uani 1 1 d . . . . .
Cl3 Cl 0.00331(10) -0.37760(9) 0.90686(6) 0.0305(2) Uani 1 1 d . . . . .
O6 O -0.2216(2) -0.5571(2) 0.52072(15) 0.0230(4) Uani 1 1 d . . . . .
O4 O -0.3356(2) -0.3427(2) 0.66995(16) 0.0266(5) Uani 1 1 d . . . . .
O2 O 0.5978(3) 0.3160(3) 0.74810(19) 0.0371(6) Uani 1 1 d . . . . .
O1 O 0.6458(3) 0.0572(3) 0.65577(19) 0.0371(6) Uani 1 1 d . . . . .
N1 N 0.0212(3) -0.3290(3) 0.6732(2) 0.0202(5) Uani 1 1 d . . . . .
C8 C 0.0842(4) -0.1851(3) 0.7836(2) 0.0178(6) Uani 1 1 d . . . . .
H8 H -0.0365 -0.1479 0.8032 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3678(4) -0.0782(3) 0.7085(2) 0.0199(6) Uani 1 1 d . . . . .
H4 H 0.3888 -0.1810 0.6706 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2154(3) -0.0493(3) 0.7713(2) 0.0165(6) Uani 1 1 d . . . . .
C9 C 0.1821(4) -0.2361(3) 0.8872(2) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.4834(4) 0.0536(4) 0.7063(2) 0.0216(6) Uani 1 1 d . . . . .
C3 C 0.4555(4) 0.2066(4) 0.7622(3) 0.0257(7) Uani 1 1 d . . . . .
C10 C -0.2320(4) -0.2932(4) 0.4881(3) 0.0351(8) Uani 1 1 d . . . . .
H10A H -0.1445 -0.3242 0.4349 0.053 Uiso 1 1 calc R U . . .
H10B H -0.1987 -0.1795 0.5319 0.053 Uiso 1 1 calc R U . . .
H10C H -0.3675 -0.3232 0.4411 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1870(4) 0.1049(3) 0.8253(2) 0.0247(7) Uani 1 1 d . . . . .
H6 H 0.0848 0.1212 0.8655 0.030 Uiso 1 1 calc R U . . .
C1 C 0.7175(5) 0.2223(4) 0.6829(4) 0.0531(11) Uani 1 1 d . . . . .
H1A H 0.8542 0.2540 0.7307 0.064 Uiso 1 1 calc R U . . .
H1B H 0.7153 0.2398 0.6079 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3069(4) 0.2375(4) 0.8214(3) 0.0315(7) Uani 1 1 d . . . . .
H7 H 0.2863 0.3409 0.8572 0.038 Uiso 1 1 calc R U . . .
H1N1 H 0.102(4) -0.352(3) 0.637(2) 0.015(8) 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
Cl2 C9 1.775(3) . ?
S1 O4 1.426(2) . ?
S1 O6 1.442(2) . ?
S1 N1 1.615(2) . ?
S1 C10 1.752(3) . ?
Cl1 C9 1.765(3) . ?
Cl3 C9 1.787(3) . ?
O2 C3 1.393(3) . ?
O2 C1 1.408(4) . ?
O1 C2 1.381(3) . ?
O1 C1 1.425(4) . ?
N1 C8 1.457(3) . ?
C8 C5 1.512(4) . ?
C8 C9 1.554(3) . ?
C4 C2 1.371(4) . ?
C4 C5 1.411(4) . ?
C5 C6 1.382(4) . ?
C2 C3 1.374(4) . ?
C3 C7 1.363(4) . ?
C6 C7 1.401(4) . ?

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
O4 S1 O6 119.40(11) . . ?
O4 S1 N1 108.01(12) . . ?
O6 S1 N1 105.33(12) . . ?
O4 S1 C10 108.99(14) . . ?
O6 S1 C10 106.70(13) . . ?
N1 S1 C10 107.89(13) . . ?
C3 O2 C1 104.8(2) . . ?
C2 O1 C1 105.0(3) . . ?
C8 N1 S1 123.2(2) . . ?
N1 C8 C5 114.0(2) . . ?
N1 C8 C9 107.0(2) . . ?
C5 C8 C9 113.47(18) . . ?
C2 C4 C5 116.4(3) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 C8 118.9(2) . . ?
C4 C5 C8 120.9(2) . . ?
C8 C9 Cl1 111.53(18) . . ?
C8 C9 Cl2 109.88(19) . . ?
Cl1 C9 Cl2 109.17(13) . . ?
C8 C9 Cl3 109.60(16) . . ?
Cl1 C9 Cl3 108.75(15) . . ?
Cl2 C9 Cl3 107.82(14) . . ?
C4 C2 C3 122.7(3) . . ?
C4 C2 O1 127.2(3) . . ?
C3 C2 O1 110.0(2) . . ?
C7 C3 C2 122.1(3) . . ?
C7 C3 O2 127.8(3) . . ?
C2 C3 O2 110.1(3) . . ?
C5 C6 C7 122.2(3) . . ?
O2 C1 O1 110.2(3) . . ?
C3 C7 C6 116.3(3) . . ?

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
O4 S1 N1 C8 -31.1(3) . . . . no
O6 S1 N1 C8 -159.7(2) . . . . no
S1 N1 C8 C5 -109.3(2) . . . . no
S1 N1 C8 C9 124.5(2) . . . . no
C4 C5 C8 N1 -41.7(3) . . . . no
C6 C5 C8 N1 139.9(2) . . . . no
N1 C8 C9 Cl1 59.4(2) . . . . no
N1 C8 C9 Cl2 -179.42(16) . . . . no
N1 C8 C9 Cl3 -61.1(2) . . . . no
C5 C8 C9 Cl1 -67.2(2) . . . . no
C5 C8 C9 Cl2 54.0(2) . . . . no
C5 C8 C9 Cl3 172.31(16) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 O4 3.172(2) . 1_655 no
Cl1 N1 3.034(2) . . no
Cl3 N1 3.026(2) . . no
O6 S1 3.497(2) . 2_546 no
O6 N1 2.891(3) . 2_546 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1N1 O6 0.78(3) 2.16(2) 2.891(3) 157(2) 2_546 yes
C1 H1B O6 0.9700 2.4600 3.296(5) 145.00 1_665 yes
C4 H4 O4 0.9300 2.5500 3.321(4) 140.00 1_655 yes
C8 H8 O4 0.9800 2.4400 2.939(3) 111.00 . yes
C10 H10C O2 0.9600 2.5700 3.389(4) 144.00 2_556 yes


_refine_diff_density_max         0.353
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-4

