# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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. # # This CIF is provided on the understanding that it is used for bona # 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 # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cbu1103 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N2 S2' _chemical_formula_sum 'C20 H20 N2 S2' _chemical_formula_weight 352.50 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.4685(3) _cell_length_b 12.1683(4) _cell_length_c 17.2063(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1773.06(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7053 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.28 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8918 _exptl_absorpt_correction_T_max 0.9313 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14660 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0089 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2038 _reflns_number_gt 1841 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0374P)^2^+0.6253P] 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 2038 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 S S -0.08559(4) 0.06451(2) 0.378101(18) 0.03134(11) Uani 1 1 d . . . N N 0.15774(16) 0.15458(11) 0.49234(7) 0.0426(3) Uani 1 1 d . . . H1NA H 0.115(2) 0.0908(16) 0.4951(10) 0.052(5) Uiso 1 1 d . . . H1NB H 0.204(2) 0.1776(14) 0.5348(11) 0.056(5) Uiso 1 1 d . . . C1 C 0.03910(14) -0.09762(9) 0.28579(7) 0.0278(2) Uani 1 1 d . . . C2 C 0.07503(15) -0.19776(11) 0.32107(8) 0.0349(3) Uani 1 1 d . . . H2 H 0.1264 -0.1982 0.3702 0.042 Uiso 1 1 calc R . . C3 C 0.03709(17) -0.29651(10) 0.28569(9) 0.0399(3) Uani 1 1 d . . . H3 H 0.0621 -0.3641 0.3105 0.048 Uiso 1 1 calc R . . C10 C 0.08518(14) 0.00839(10) 0.32520(7) 0.0314(3) Uani 1 1 d . . . H10A H 0.1216 0.0621 0.2859 0.038 Uiso 1 1 calc R . . H10B H 0.1731 -0.0052 0.3619 0.038 Uiso 1 1 calc R . . C11 C -0.02919(14) 0.20340(9) 0.39152(6) 0.0267(2) Uani 1 1 d . . . C12 C 0.07829(14) 0.23289(10) 0.45021(7) 0.0295(3) Uani 1 1 d . . . C13 C 0.10865(16) 0.34527(11) 0.46173(8) 0.0349(3) Uani 1 1 d . . . H13 H 0.1785 0.3675 0.5020 0.042 Uiso 1 1 calc R . . C14 C 0.03833(16) 0.42377(10) 0.41528(8) 0.0365(3) Uani 1 1 d . . . H14 H 0.0604 0.4993 0.4242 0.044 Uiso 1 1 calc R . . C15 C -0.06340(16) 0.39462(11) 0.35613(8) 0.0372(3) Uani 1 1 d . . . H15 H -0.1093 0.4492 0.3237 0.045 Uiso 1 1 calc R . . C16 C -0.09756(15) 0.28428(10) 0.34474(7) 0.0324(3) Uani 1 1 d . . . H16 H -0.1685 0.2634 0.3046 0.039 Uiso 1 1 calc R . . 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 S 0.03392(18) 0.02513(17) 0.03497(19) -0.00366(11) 0.00228(12) -0.00570(11) N 0.0529(7) 0.0348(6) 0.0401(6) 0.0037(5) -0.0164(6) -0.0038(5) C1 0.0279(5) 0.0228(5) 0.0328(6) -0.0008(5) -0.0017(5) 0.0007(4) C2 0.0371(6) 0.0303(6) 0.0372(7) 0.0056(5) -0.0031(5) 0.0032(5) C3 0.0423(7) 0.0221(6) 0.0553(8) 0.0082(5) 0.0042(6) 0.0036(5) C10 0.0300(6) 0.0275(6) 0.0368(6) -0.0054(5) -0.0042(5) -0.0003(5) C11 0.0291(6) 0.0239(5) 0.0272(5) -0.0019(4) 0.0035(4) -0.0012(4) C12 0.0326(6) 0.0287(6) 0.0271(6) -0.0011(5) 0.0022(5) -0.0013(5) C13 0.0377(6) 0.0317(6) 0.0352(6) -0.0076(5) 0.0032(5) -0.0060(5) C14 0.0431(7) 0.0244(6) 0.0420(7) -0.0040(5) 0.0149(6) -0.0014(5) C15 0.0422(7) 0.0294(6) 0.0402(7) 0.0064(5) 0.0105(6) 0.0080(5) C16 0.0334(6) 0.0329(6) 0.0309(6) 0.0004(5) 0.0020(5) 0.0037(5) _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 S C11 1.7714(12) . ? S C10 1.8402(13) . ? N C12 1.3733(17) . ? N H1NA 0.859(19) . ? N H1NB 0.877(19) . ? C1 C2 1.3949(17) . ? C1 C1 1.399(2) 3 ? C1 C10 1.5086(16) . ? C2 C3 1.3849(19) . ? C3 C3 1.379(3) 3 ? C11 C16 1.3970(17) . ? C11 C12 1.4061(16) . ? C12 C13 1.4055(17) . ? C13 C14 1.3806(19) . ? C14 C15 1.380(2) . ? C15 C16 1.3873(18) . ? 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 S C10 101.92(5) . . ? C12 N H1NA 116.6(12) . . ? C12 N H1NB 116.0(11) . . ? H1NA N H1NB 115.8(16) . . ? C2 C1 C1 119.11(7) . 3 ? C2 C1 C10 119.67(11) . . ? C1 C1 C10 121.22(7) 3 . ? C3 C2 C1 121.07(12) . . ? C3 C3 C2 119.81(8) 3 . ? C1 C10 S 109.66(8) . . ? C16 C11 C12 120.16(11) . . ? C16 C11 S 119.03(9) . . ? C12 C11 S 120.77(9) . . ? N C12 C13 120.73(12) . . ? N C12 C11 121.28(11) . . ? C13 C12 C11 117.90(11) . . ? C14 C13 C12 120.85(12) . . ? C15 C14 C13 121.23(12) . . ? C14 C15 C16 118.89(12) . . ? C15 C16 C11 120.93(12) . . ? 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 C1 C1 C2 C3 1.2(2) 3 . . . ? C10 C1 C2 C3 -178.73(12) . . . . ? C1 C2 C3 C3 0.2(2) . . . 3 ? C2 C1 C10 S -98.00(12) . . . . ? C1 C1 C10 S 82.09(16) 3 . . . ? C11 S C10 C1 -161.66(8) . . . . ? C10 S C11 C16 103.65(10) . . . . ? C10 S C11 C12 -78.72(10) . . . . ? C16 C11 C12 N -174.13(12) . . . . ? S C11 C12 N 8.27(16) . . . . ? C16 C11 C12 C13 2.47(17) . . . . ? S C11 C12 C13 -175.13(9) . . . . ? N C12 C13 C14 174.81(12) . . . . ? C11 C12 C13 C14 -1.80(18) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C13 C14 C15 C16 1.4(2) . . . . ? C14 C15 C16 C11 -0.75(19) . . . . ? C12 C11 C16 C15 -1.23(18) . . . . ? S C11 C16 C15 176.41(10) . . . . ? C2 C1 C1 C2 -1.8(3) . . 3 3 ? C2 C1 C1 C10 178.08(8) . . 3 3 ? C10 C1 C1 C10 -2.0(2) . . 3 3 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.279 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 967363'