# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_gkn5
_database_code_depnum_ccdc_archive 'CCDC 1046740'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H11 Cl2 N3 O2 S'
_chemical_formula_weight         416.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   8.5087(8)
_cell_length_b                   10.5551(10)
_cell_length_c                   10.9292(11)
_cell_angle_alpha                101.832(5)
_cell_angle_beta                 90.563(5)
_cell_angle_gamma                111.879(5)
_cell_volume                     887.47(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2937
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      64.78

_exptl_crystal_description       rectangle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    4.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.292
_exptl_absorpt_correction_T_max  0.319
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10058
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         64.78
_reflns_number_total             2937
_reflns_number_gt                2444
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0968P)²+0.1708P] 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         2937
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1373
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5395(3) 0.3711(2) 0.7996(2) 0.0378(6) Uani 1 1 d . . .
N2 N 0.3902(3) 0.3081(2) 0.7256(2) 0.0347(5) Uani 1 1 d . . .
C3 C 0.3543(3) 0.3970(3) 0.6685(3) 0.0342(6) Uani 1 1 d . . .
H3 H 0.2588 0.3754 0.6139 0.041 Uiso 1 1 calc R . .
C4 C 0.4868(3) 0.5271(3) 0.7066(3) 0.0328(6) Uani 1 1 d . . .
C5 C 0.5979(3) 0.5037(3) 0.7895(3) 0.0338(6) Uani 1 1 d . . .
C6 C 0.5191(3) 0.6559(3) 0.6663(3) 0.0336(6) Uani 1 1 d . . .
H6 H 0.6216 0.7292 0.6991 0.040 Uiso 1 1 calc R . .
C7 C 0.4204(3) 0.6830(3) 0.5881(3) 0.0327(6) Uani 1 1 d . . .
S8 S 0.21687(9) 0.57218(7) 0.51556(8) 0.0422(3) Uani 1 1 d . . .
C9 C 0.2017(3) 0.7035(3) 0.4429(3) 0.0368(7) Uani 1 1 d . . .
N10 N 0.3480(3) 0.8211(2) 0.4727(2) 0.0351(5) Uani 1 1 d . . .
H10 H 0.3617 0.8931 0.4424 0.042 Uiso 1 1 calc R . .
C11 C 0.4719(3) 0.8198(3) 0.5528(3) 0.0325(6) Uani 1 1 d . . .
O12 O 0.6061(2) 0.9189(2) 0.5886(2) 0.0437(5) Uani 1 1 d . . .
O13 O 0.0787(3) 0.6895(2) 0.3777(2) 0.0510(6) Uani 1 1 d . . .
C14 C 0.2904(3) 0.1629(3) 0.7184(3) 0.0332(6) Uani 1 1 d . . .
C15 C 0.1244(4) 0.1038(3) 0.6660(3) 0.0399(7) Uani 1 1 d . . .
H15 H 0.0759 0.1573 0.6339 0.048 Uiso 1 1 calc R . .
C16 C 0.0302(4) -0.0365(3) 0.6616(3) 0.0460(7) Uani 1 1 d . . .
H16 H -0.0815 -0.0776 0.6251 0.055 Uiso 1 1 calc R . .
C17 C 0.1011(4) -0.1153(3) 0.7110(3) 0.0455(7) Uani 1 1 d . . .
H17 H 0.0375 -0.2094 0.7079 0.055 Uiso 1 1 calc R . .
C18 C 0.2659(4) -0.0543(3) 0.7646(3) 0.0460(8) Uani 1 1 d . . .
H18 H 0.3130 -0.1073 0.7990 0.055 Uiso 1 1 calc R . .
C19 C 0.3629(4) 0.0848(3) 0.7684(3) 0.0400(7) Uani 1 1 d . . .
H19 H 0.4751 0.1252 0.8039 0.048 Uiso 1 1 calc R . .
C20 C 0.7569(3) 0.6055(3) 0.8629(3) 0.0344(6) Uani 1 1 d . . .
C21 C 0.7612(4) 0.7297(3) 0.9382(3) 0.0396(7) Uani 1 1 d . . .
H21 H 0.6642 0.7506 0.9394 0.047 Uiso 1 1 calc R . .
C22 C 0.9071(4) 0.8225(3) 1.0110(3) 0.0435(7) Uani 1 1 d . . .
H22 H 0.9077 0.9049 1.0620 0.052 Uiso 1 1 calc R . .
C23 C 1.0532(4) 0.7938(3) 1.0086(3) 0.0408(7) Uani 1 1 d . . .
C24 C 1.0510(4) 0.6713(3) 0.9323(3) 0.0376(7) Uani 1 1 d . . .
C25 C 0.9033(4) 0.5768(3) 0.8598(3) 0.0377(7) Uani 1 1 d . . .
H25 H 0.9025 0.4942 0.8091 0.045 Uiso 1 1 calc R . .
Cl26 Cl 1.23383(11) 0.91234(9) 1.10124(9) 0.0651(3) Uani 1 1 d . . .
Cl27 Cl 1.23309(10) 0.63391(9) 0.92190(9) 0.0564(3) Uani 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
N1 C5 1.329(4) . ?
N1 N2 1.357(3) . ?
N2 C3 1.347(3) . ?
N2 C14 1.434(3) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.423(4) . ?
C4 C6 1.444(4) . ?
C5 C20 1.473(4) . ?
C6 C7 1.336(4) . ?
C6 H6 0.9300 . ?
C7 C11 1.478(4) . ?
C7 S8 1.755(3) . ?
S8 C9 1.775(3) . ?
C9 O13 1.205(3) . ?
C9 N10 1.368(3) . ?
N10 C11 1.369(4) . ?
N10 H10 0.8600 . ?
C11 O12 1.219(3) . ?
C14 C15 1.376(4) . ?
C14 C19 1.385(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.385(4) . ?
C20 C25 1.387(4) . ?
C21 C22 1.374(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(4) . ?
C23 Cl26 1.723(3) . ?
C24 C25 1.387(4) . ?
C24 Cl27 1.735(3) . ?
C25 H25 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
C5 N1 N2 105.0(2) . . ?
C3 N2 N1 112.5(2) . . ?
C3 N2 C14 128.2(2) . . ?
N1 N2 C14 119.3(2) . . ?
N2 C3 C4 107.1(2) . . ?
N2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C3 C4 C5 103.9(2) . . ?
C3 C4 C6 130.1(2) . . ?
C5 C4 C6 125.8(2) . . ?
N1 C5 C4 111.5(2) . . ?
N1 C5 C20 119.8(2) . . ?
C4 C5 C20 128.6(2) . . ?
C7 C6 C4 128.2(2) . . ?
C7 C6 H6 115.9 . . ?
C4 C6 H6 115.9 . . ?
C6 C7 C11 122.4(2) . . ?
C6 C7 S8 127.8(2) . . ?
C11 C7 S8 109.84(19) . . ?
C7 S8 C9 91.64(12) . . ?
O13 C9 N10 125.7(3) . . ?
O13 C9 S8 124.1(2) . . ?
N10 C9 S8 110.19(19) . . ?
C9 N10 C11 117.4(2) . . ?
C9 N10 H10 121.3 . . ?
C11 N10 H10 121.3 . . ?
O12 C11 N10 123.7(2) . . ?
O12 C11 C7 125.4(2) . . ?
N10 C11 C7 110.9(2) . . ?
C15 C14 C19 120.8(3) . . ?
C15 C14 N2 120.5(2) . . ?
C19 C14 N2 118.6(2) . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C14 118.9(3) . . ?
C18 C19 H19 120.6 . . ?
C14 C19 H19 120.6 . . ?
C21 C20 C25 119.1(3) . . ?
C21 C20 C5 120.4(2) . . ?
C25 C20 C5 120.5(3) . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.4(3) . . ?
C24 C23 Cl26 121.6(2) . . ?
C22 C23 Cl26 119.0(2) . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 Cl27 121.0(2) . . ?
C25 C24 Cl27 118.5(2) . . ?
C20 C25 C24 120.0(3) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        64.78
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.075
