# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O2 S'
_chemical_formula_sum            'C15 H16 N2 O2 S'
_chemical_formula_weight         288.36

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   15.9574(4)
_cell_length_b                   6.03640(10)
_cell_length_c                   14.9838(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.9360(10)
_cell_angle_gamma                90.00
_cell_volume                     1348.03(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9833
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      31.205

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.9034
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            72839
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         33.25
_reflns_number_total             5158
_reflns_number_gt                4094
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        ?
_computing_structure_solution    'SIR 2004 (Burla, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3 (CCDC, 2009)'
_computing_publication_material  'WinGX 1.80.05 (Farrugia, 1998)'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0509P)^2^+0.5404P] where P=(Fo^2^+2Fc^2^)/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         5158
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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
N2 N 0.55654(7) -0.19692(16) 0.36384(7) 0.01789(19) Uani 1 1 d . . .
C9 C 0.64624(7) -0.14847(18) 0.42835(8) 0.0167(2) Uani 1 1 d . . .
H9A H 0.6898 -0.2413 0.4119 0.020 Uiso 1 1 calc R . .
H9B H 0.6515 -0.1842 0.4946 0.020 Uiso 1 1 calc R . .
N3 N 0.66721(6) 0.08873(16) 0.42191(6) 0.01499(17) Uani 1 1 d . . .
C9A C 0.49112(7) -0.03274(19) 0.35140(7) 0.0161(2) Uani 1 1 d . . .
C10 C 0.40217(8) -0.0747(2) 0.29075(8) 0.0195(2) Uani 1 1 d . . .
H10 H 0.3870 -0.2134 0.2590 0.023 Uiso 1 1 calc R . .
C11 C 0.33661(7) 0.0858(2) 0.27718(8) 0.0201(2) Uani 1 1 d . . .
H11 H 0.2768 0.0565 0.2360 0.024 Uiso 1 1 calc R . .
C12 C 0.35777(8) 0.2894(2) 0.32335(8) 0.0208(2) Uani 1 1 d . . .
H12 H 0.3126 0.3984 0.3144 0.025 Uiso 1 1 calc R . .
C13 C 0.44567(7) 0.3317(2) 0.38276(8) 0.0179(2) Uani 1 1 d . . .
H13 H 0.4603 0.4709 0.4141 0.022 Uiso 1 1 calc R . .
C13A C 0.51260(7) 0.17326(18) 0.39706(7) 0.01509(19) Uani 1 1 d . . .
C14 C 0.60920(7) 0.22840(19) 0.45618(8) 0.0166(2) Uani 1 1 d . . .
H14A H 0.6212 0.3870 0.4489 0.020 Uiso 1 1 calc R . .
H14B H 0.6211 0.1986 0.5246 0.020 Uiso 1 1 calc R . .
S1 S 0.773630(17) 0.15356(5) 0.454971(18) 0.01498(7) Uani 1 1 d . . .
O2 O 0.77777(5) 0.38975(14) 0.44641(6) 0.02105(18) Uani 1 1 d . . .
O3 O 0.81061(6) 0.01162(15) 0.40165(6) 0.02099(17) Uani 1 1 d . . .
C15 C 0.82461(7) 0.08438(18) 0.57656(7) 0.01494(19) Uani 1 1 d . . .
C16 C 0.82808(7) 0.24189(19) 0.64585(8) 0.0176(2) Uani 1 1 d . . .
H16 H 0.8032 0.3852 0.6277 0.021 Uiso 1 1 calc R . .
C17 C 0.86839(8) 0.1868(2) 0.74194(8) 0.0195(2) Uani 1 1 d . . .
H17 H 0.8711 0.2938 0.7894 0.023 Uiso 1 1 calc R . .
C18 C 0.90475(7) -0.0228(2) 0.76961(8) 0.0189(2) Uani 1 1 d . . .
C18A C 0.94855(8) -0.0819(3) 0.87373(9) 0.0267(3) Uani 1 1 d . . .
H18A H 0.9577 -0.2425 0.8801 0.040 Uiso 0.443(19) 1 calc PR A 1
H18B H 0.9098 -0.0351 0.9084 0.040 Uiso 0.443(19) 1 calc PR A 1
H18C H 1.0066 -0.0065 0.9004 0.040 Uiso 0.443(19) 1 calc PR A 1
H18D H 0.9582 0.0504 0.9117 0.040 Uiso 0.557(19) 1 d PR A 2
H18E H 1.0051 -0.1529 0.8841 0.040 Uiso 0.557(19) 1 d PR A 2
H18F H 0.9103 -0.1808 0.8919 0.040 Uiso 0.557(19) 1 d PR A 2
C19 C 0.89974(8) -0.1784(2) 0.69886(8) 0.0191(2) Uani 1 1 d . . .
H19 H 0.9240 -0.3222 0.7170 0.023 Uiso 1 1 calc R . .
C20 C 0.85993(7) -0.12707(19) 0.60235(8) 0.0175(2) Uani 1 1 d . . .
H20 H 0.8569 -0.2343 0.5549 0.021 Uiso 1 1 calc R . .
H2 H 0.5550(12) -0.262(3) 0.3104(13) 0.033(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0198(5) 0.0146(4) 0.0180(4) -0.0030(3) 0.0053(4) -0.0014(3)
C9 0.0181(5) 0.0132(5) 0.0178(5) 0.0007(4) 0.0051(4) -0.0012(4)
N3 0.0143(4) 0.0135(4) 0.0168(4) 0.0002(3) 0.0051(3) 0.0000(3)
C9A 0.0182(5) 0.0166(5) 0.0141(4) 0.0007(4) 0.0065(4) -0.0022(4)
C10 0.0203(5) 0.0210(5) 0.0165(5) -0.0014(4) 0.0058(4) -0.0059(4)
C11 0.0142(5) 0.0281(6) 0.0177(5) 0.0009(4) 0.0053(4) -0.0045(4)
C12 0.0164(5) 0.0265(6) 0.0206(5) 0.0010(4) 0.0080(4) 0.0008(4)
C13 0.0171(5) 0.0192(5) 0.0185(5) -0.0010(4) 0.0076(4) 0.0001(4)
C13A 0.0151(5) 0.0165(5) 0.0141(4) -0.0013(4) 0.0058(4) -0.0022(4)
C14 0.0147(5) 0.0158(5) 0.0190(5) -0.0028(4) 0.0054(4) 0.0011(4)
S1 0.01387(12) 0.01513(12) 0.01634(12) 0.00244(9) 0.00587(9) 0.00032(9)
O2 0.0191(4) 0.0158(4) 0.0273(4) 0.0059(3) 0.0071(3) -0.0012(3)
O3 0.0215(4) 0.0251(4) 0.0197(4) 0.0015(3) 0.0114(3) 0.0032(3)
C15 0.0129(4) 0.0154(5) 0.0161(4) 0.0001(4) 0.0048(4) -0.0004(4)
C16 0.0160(5) 0.0161(5) 0.0214(5) -0.0016(4) 0.0075(4) -0.0003(4)
C17 0.0168(5) 0.0232(6) 0.0193(5) -0.0051(4) 0.0076(4) -0.0029(4)
C18 0.0119(5) 0.0271(6) 0.0169(5) 0.0006(4) 0.0042(4) -0.0028(4)
C18A 0.0209(6) 0.0402(7) 0.0174(5) 0.0032(5) 0.0051(4) -0.0013(5)
C19 0.0155(5) 0.0196(5) 0.0200(5) 0.0027(4) 0.0037(4) 0.0015(4)
C20 0.0163(5) 0.0167(5) 0.0180(5) -0.0008(4) 0.0043(4) 0.0015(4)

_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
N2 C9A 1.4027(15) . ?
N2 C9 1.4423(15) . ?
N2 H2 0.885(18) . ?
C9 N3 1.4814(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N3 C14 1.4734(14) . ?
N3 S1 1.6374(9) . ?
C9A C13A 1.4015(15) . ?
C9A C10 1.4082(16) . ?
C10 C11 1.3864(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3914(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3903(16) . ?
C12 H12 0.9500 . ?
C13 C13A 1.3922(16) . ?
C13 H13 0.9500 . ?
C13A C14 1.5152(15) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
S1 O3 1.4344(9) . ?
S1 O2 1.4351(9) . ?
S1 C15 1.7596(11) . ?
C15 C20 1.3930(16) . ?
C15 C16 1.3942(15) . ?
C16 C17 1.3913(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3918(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3970(17) . ?
C18 C18A 1.5068(16) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C18A H18D 0.9606 . ?
C18A H18E 0.9606 . ?
C18A H18F 0.9606 . ?
C19 C20 1.3906(16) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C9A N2 C9 117.33(9) . . ?
C9A N2 H2 114.6(11) . . ?
C9 N2 H2 113.3(12) . . ?
N2 C9 N3 110.21(9) . . ?
N2 C9 H9A 109.6 . . ?
N3 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
N3 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C14 N3 C9 110.22(8) . . ?
C14 N3 S1 118.07(7) . . ?
C9 N3 S1 116.44(7) . . ?
C13A C9A N2 121.43(10) . . ?
C13A C9A C10 119.27(10) . . ?
N2 C9A C10 119.30(10) . . ?
C11 C10 C9A 120.18(11) . . ?
C11 C10 H10 119.9 . . ?
C9A C10 H10 119.9 . . ?
C10 C11 C12 120.53(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.39(11) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C13A 121.01(11) . . ?
C12 C13 H13 119.5 . . ?
C13A C13 H13 119.5 . . ?
C13 C13A C9A 119.61(10) . . ?
C13 C13A C14 120.22(10) . . ?
C9A C13A C14 120.04(10) . . ?
N3 C14 C13A 107.77(9) . . ?
N3 C14 H14A 110.2 . . ?
C13A C14 H14A 110.2 . . ?
N3 C14 H14B 110.2 . . ?
C13A C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
O3 S1 O2 120.16(5) . . ?
O3 S1 N3 106.10(5) . . ?
O2 S1 N3 106.63(5) . . ?
O3 S1 C15 107.75(5) . . ?
O2 S1 C15 108.02(5) . . ?
N3 S1 C15 107.60(5) . . ?
C20 C15 C16 120.92(10) . . ?
C20 C15 S1 119.75(8) . . ?
C16 C15 S1 119.33(9) . . ?
C17 C16 C15 119.22(11) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.99(11) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 118.70(10) . . ?
C17 C18 C18A 120.89(11) . . ?
C19 C18 C18A 120.41(12) . . ?
C18 C18A H18A 109.5 . . ?
C18 C18A H18B 109.5 . . ?
C18 C18A H18C 109.5 . . ?
C18 C18A H18D 109.5 . . ?
C18 C18A H18E 109.6 . . ?
H18D C18A H18E 109.4 . . ?
C18 C18A H18F 109.5 . . ?
H18D C18A H18F 109.4 . . ?
H18E C18A H18F 109.4 . . ?
C20 C19 C18 121.36(11) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C15 118.80(10) . . ?
C19 C20 H20 120.6 . . ?
C15 C20 H20 120.6 . . ?

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
C9A N2 C9 N3 -35.88(13) . . . . ?
N2 C9 N3 C14 65.40(11) . . . . ?
N2 C9 N3 S1 -156.58(7) . . . . ?
C9 N2 C9A C13A 2.26(15) . . . . ?
C9 N2 C9A C10 -178.58(10) . . . . ?
C13A C9A C10 C11 -0.53(16) . . . . ?
N2 C9A C10 C11 -179.71(10) . . . . ?
C9A C10 C11 C12 -0.18(17) . . . . ?
C10 C11 C12 C13 0.60(17) . . . . ?
C11 C12 C13 C13A -0.32(17) . . . . ?
C12 C13 C13A C9A -0.38(16) . . . . ?
C12 C13 C13A C14 175.48(10) . . . . ?
N2 C9A C13A C13 179.97(10) . . . . ?
C10 C9A C13A C13 0.80(15) . . . . ?
N2 C9A C13A C14 4.10(15) . . . . ?
C10 C9A C13A C14 -175.07(10) . . . . ?
C9 N3 C14 C13A -57.05(11) . . . . ?
S1 N3 C14 C13A 165.70(7) . . . . ?
C13 C13A C14 N3 -152.35(10) . . . . ?
C9A C13A C14 N3 23.50(13) . . . . ?
C14 N3 S1 O3 -172.29(8) . . . . ?
C9 N3 S1 O3 53.05(9) . . . . ?
C14 N3 S1 O2 -43.10(9) . . . . ?
C9 N3 S1 O2 -177.75(8) . . . . ?
C14 N3 S1 C15 72.59(9) . . . . ?
C9 N3 S1 C15 -62.06(9) . . . . ?
O3 S1 C15 C20 -24.85(10) . . . . ?
O2 S1 C15 C20 -156.06(9) . . . . ?
N3 S1 C15 C20 89.17(9) . . . . ?
O3 S1 C15 C16 155.90(9) . . . . ?
O2 S1 C15 C16 24.69(10) . . . . ?
N3 S1 C15 C16 -90.08(10) . . . . ?
C20 C15 C16 C17 0.73(16) . . . . ?
S1 C15 C16 C17 179.97(8) . . . . ?
C15 C16 C17 C18 -0.27(17) . . . . ?
C16 C17 C18 C19 -0.29(17) . . . . ?
C16 C17 C18 C18A 179.87(11) . . . . ?
C17 C18 C19 C20 0.41(17) . . . . ?
C18A C18 C19 C20 -179.75(11) . . . . ?
C18 C19 C20 C15 0.03(17) . . . . ?
C16 C15 C20 C19 -0.61(16) . . . . ?
S1 C15 C20 C19 -179.85(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        33.25
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 939751'