# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_k
_database_code_depnum_ccdc_archive 'CCDC 986043'
_audit_update_record             
;
2014-08-04 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N3 O S'
_chemical_formula_sum            'C13 H11 N3 O S'
_chemical_formula_weight         257.31

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   5.2573(8)
_cell_length_b                   20.338(3)
_cell_length_c                   11.7359(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.393(2)
_cell_angle_gamma                90.00
_cell_volume                     1254.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1864
_cell_measurement_theta_min      2.650
_cell_measurement_theta_max      27.551

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9247
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8081
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2343
_reflns_number_gt                1720
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'


_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)+(0.0416P)²+0.2140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2343
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31296(12) 0.59048(3) 0.99937(4) 0.04170(19) Uani 1 1 d . . .
O1 O 0.5639(3) 0.56601(7) 0.63337(11) 0.0414(4) Uani 1 1 d . . .
N1 N 0.5763(3) 0.54752(8) 0.82482(13) 0.0281(4) Uani 1 1 d . . .
N2 N 0.2955(3) 0.62999(8) 0.78103(13) 0.0317(4) Uani 1 1 d . . .
N3 N 0.0783(4) 0.70433(9) 0.67718(14) 0.0462(5) Uani 1 1 d . . .
C1 C 0.3922(4) 0.59147(9) 0.86194(15) 0.0271(4) Uani 1 1 d . . .
C2 C 0.1056(4) 0.67876(10) 0.78122(15) 0.0302(5) Uani 1 1 d . . .
C3 C -0.0379(4) 0.69895(11) 0.87327(18) 0.0398(5) Uani 1 1 d . . .
C4 C -0.2154(4) 0.74756(12) 0.8555(2) 0.0462(6) Uani 1 1 d . . .
C5 C -0.2466(5) 0.77436(13) 0.7493(2) 0.0497(6) Uani 1 1 d . . .
C6 C -0.0961(5) 0.75110(13) 0.6636(2) 0.0574(7) Uani 1 1 d . . .
C11 C 0.6512(3) 0.53495(10) 0.71400(15) 0.0289(5) Uani 1 1 d . . .
C12 C 0.8411(3) 0.48202(9) 0.69679(15) 0.0268(4) Uani 1 1 d . . .
C13 C 0.8401(4) 0.45072(10) 0.59085(16) 0.0319(5) Uani 1 1 d . . .
C14 C 1.0196(4) 0.40345(11) 0.56650(18) 0.0368(5) Uani 1 1 d . . .
C15 C 1.2023(4) 0.38733(11) 0.64678(19) 0.0394(5) Uani 1 1 d . . .
C16 C 1.2025(4) 0.41736(11) 0.7519(2) 0.0380(5) Uani 1 1 d . . .
C17 C 1.0219(4) 0.46453(10) 0.77794(17) 0.0313(5) Uani 1 1 d . . .
H1 H 0.629(3) 0.5210(10) 0.8733(16) 0.027(6) Uiso 1 1 d . . .
H2 H 0.353(4) 0.6226(11) 0.717(2) 0.048(7) Uiso 1 1 d . . .
H3 H -0.010(4) 0.6775(11) 0.9426(19) 0.055(7) Uiso 1 1 d . . .
H4 H -0.319(5) 0.7637(12) 0.913(2) 0.069(8) Uiso 1 1 d . . .
H5 H -0.363(4) 0.8093(13) 0.7350(18) 0.057(7) Uiso 1 1 d . . .
H6 H -0.115(4) 0.7667(12) 0.592(2) 0.063(7) Uiso 1 1 d . . .
H13 H 0.705(4) 0.4619(10) 0.5347(16) 0.037(5) Uiso 1 1 d . . .
H14 H 1.018(4) 0.3805(10) 0.4966(18) 0.040(6) Uiso 1 1 d . . .
H15 H 1.329(4) 0.3545(11) 0.6275(18) 0.050(6) Uiso 1 1 d . . .
H16 H 1.321(4) 0.4077(11) 0.8032(18) 0.044(6) Uiso 1 1 d . . .
H17 H 1.026(3) 0.4864(9) 0.8485(16) 0.027(5) 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 C1 1.6686(18) . ?
O1 C11 1.224(2) . ?
N1 C11 1.385(2) . ?
N1 C1 1.390(2) . ?
N1 H1 0.83(2) . ?
N2 C1 1.329(2) . ?
N2 C2 1.407(2) . ?
N2 H2 0.82(2) . ?
N3 C6 1.330(3) . ?
N3 C2 1.334(2) . ?
C2 C3 1.384(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.93(2) . ?
C4 C5 1.369(3) . ?
C4 H4 0.93(2) . ?
C5 C6 1.368(3) . ?
C5 H5 0.95(2) . ?
C6 H6 0.91(2) . ?
C11 C12 1.483(3) . ?
C12 C17 1.387(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.991(19) . ?
C14 C15 1.380(3) . ?
C14 H14 0.94(2) . ?
C15 C16 1.376(3) . ?
C15 H15 0.97(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.89(2) . ?
C17 H17 0.940(19) . ?

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
C11 N1 C1 128.03(17) . . ?
C11 N1 H1 115.4(13) . . ?
C1 N1 H1 115.5(13) . . ?
C1 N2 C2 133.00(17) . . ?
C1 N2 H2 113.6(16) . . ?
C2 N2 H2 113.3(16) . . ?
C6 N3 C2 117.26(18) . . ?
N2 C1 N1 114.76(16) . . ?
N2 C1 S1 126.93(15) . . ?
N1 C1 S1 118.31(14) . . ?
N3 C2 C3 122.87(19) . . ?
N3 C2 N2 110.20(16) . . ?
C3 C2 N2 126.93(18) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 H3 124.8(14) . . ?
C2 C3 H3 117.2(14) . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 117.1(16) . . ?
C3 C4 H4 122.8(16) . . ?
C6 C5 C4 117.7(2) . . ?
C6 C5 H5 120.2(13) . . ?
C4 C5 H5 122.0(13) . . ?
N3 C6 C5 124.2(2) . . ?
N3 C6 H6 115.7(16) . . ?
C5 C6 H6 120.1(16) . . ?
O1 C11 N1 121.54(18) . . ?
O1 C11 C12 121.22(16) . . ?
N1 C11 C12 117.25(16) . . ?
C17 C12 C13 119.50(18) . . ?
C17 C12 C11 123.46(17) . . ?
C13 C12 C11 116.99(17) . . ?
C14 C13 C12 120.27(19) . . ?
C14 C13 H13 120.7(11) . . ?
C12 C13 H13 119.0(11) . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 121.6(13) . . ?
C15 C14 H14 118.5(13) . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 121.2(13) . . ?
C14 C15 H15 118.6(13) . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 120.5(14) . . ?
C17 C16 H16 118.9(14) . . ?
C16 C17 C12 119.6(2) . . ?
C16 C17 H17 120.7(11) . . ?
C12 C17 H17 119.6(11) . . ?

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
C2 N2 C1 N1 178.14(19) . . . . ?
C2 N2 C1 S1 -1.1(3) . . . . ?
C11 N1 C1 N2 -6.8(3) . . . . ?
C11 N1 C1 S1 172.49(15) . . . . ?
C6 N3 C2 C3 -0.1(3) . . . . ?
C6 N3 C2 N2 179.7(2) . . . . ?
C1 N2 C2 N3 179.4(2) . . . . ?
C1 N2 C2 C3 -0.8(4) . . . . ?
N3 C2 C3 C4 -0.1(3) . . . . ?
N2 C2 C3 C4 -179.8(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C2 N3 C6 C5 0.2(4) . . . . ?
C4 C5 C6 N3 -0.1(4) . . . . ?
C1 N1 C11 O1 3.8(3) . . . . ?
C1 N1 C11 C12 -175.93(17) . . . . ?
O1 C11 C12 C17 151.73(19) . . . . ?
N1 C11 C12 C17 -28.5(3) . . . . ?
O1 C11 C12 C13 -25.6(3) . . . . ?
N1 C11 C12 C13 154.11(17) . . . . ?
C17 C12 C13 C14 -0.9(3) . . . . ?
C11 C12 C13 C14 176.60(17) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C12 -0.6(3) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
C11 C12 C17 C16 -175.86(18) . . . . ?

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
N2 H2 O1 0.82(2) 1.88(2) 2.592(2) 144(2) .
N1 H1 S1 0.83(2) 2.73(2) 3.5293(18) 161.8(17) 3_667

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
