# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 N4 O4 S2' _chemical_formula_weight 372.46 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' '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 9.2078(4) _cell_length_b 7.9309(4) _cell_length_c 11.4536(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.796(4) _cell_angle_gamma 90.00 _cell_volume 836.00(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5426 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 29.99 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.346 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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_standards_number 'n/a' _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count 'n/a' _diffrn_standards_interval_time 'n/a' _diffrn_standards_decay_% 'n/a' _diffrn_reflns_number 5426 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 29.99 _reflns_number_total 2337 _reflns_number_gt 1783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON(Spek,2004)' _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.0000P] 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 2337 _refine_ls_number_parameters 124 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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 C11 C 0.16711(17) 0.36854(17) 0.44715(11) 0.0168(3) Uani 1 1 d . . . C12 C 0.28343(18) 0.36326(19) 0.52997(12) 0.0216(3) Uani 1 1 d . . . H12 H 0.3678 0.4231 0.5152 0.026 Uiso 1 1 calc R . . C13 C 0.27616(19) 0.2719(2) 0.63251(13) 0.0252(4) Uani 1 1 d . . . H13 H 0.3539 0.2722 0.6863 0.030 Uiso 1 1 calc R . . C14 C 0.15186(19) 0.17976(19) 0.65441(13) 0.0245(3) Uani 1 1 d . . . H14 H 0.1470 0.1166 0.7226 0.029 Uiso 1 1 calc R . . C15 C 0.03519(18) 0.18144(18) 0.57541(12) 0.0216(3) Uani 1 1 d . . . H15 H -0.0477 0.1193 0.5907 0.026 Uiso 1 1 calc R . . C16 C 0.04120(17) 0.27612(18) 0.47253(12) 0.0174(3) Uani 1 1 d . . . C17 C 0.18582(16) 0.47198(17) 0.33921(11) 0.0172(3) Uani 1 1 d . . . S17 S 0.34604(4) 0.55803(5) 0.30417(3) 0.02314(12) Uani 1 1 d . . . N17 N 0.06853(14) 0.49440(15) 0.27038(10) 0.0200(3) Uani 1 1 d . . . H17 H -0.0112 0.4472 0.2899 0.024 Uiso 1 1 calc R . . O16 O -0.07467(12) 0.27841(14) 0.39561(8) 0.0222(2) Uani 1 1 d D . . H16 H -0.1468(17) 0.233(2) 0.4282(14) 0.027 Uiso 1 1 d D . . O1 O 0.31823(13) 0.83723(15) 0.51695(10) 0.0279(3) Uani 1 1 d D . . H1 H 0.341(2) 0.764(2) 0.4684(13) 0.033 Uiso 1 1 d D . . H2 H 0.3823(19) 0.867(2) 0.5627(14) 0.033 Uiso 1 1 d D . . N18 N 0.06734(17) 0.59182(18) 0.16648(11) 0.0269(3) Uani 1 1 d D . . H181 H 0.126(2) 0.545(2) 0.1215(14) 0.032 Uiso 1 1 d D . . H182 H 0.103(2) 0.6897(18) 0.1859(14) 0.032 Uiso 1 1 d 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 C11 0.0185(8) 0.0157(7) 0.0161(6) -0.0021(5) -0.0012(6) 0.0014(5) C12 0.0185(8) 0.0231(8) 0.0228(7) -0.0004(6) -0.0037(6) -0.0011(6) C13 0.0270(9) 0.0260(8) 0.0221(7) 0.0011(6) -0.0073(7) 0.0020(6) C14 0.0315(10) 0.0231(8) 0.0190(6) 0.0025(6) -0.0009(6) 0.0029(6) C15 0.0245(9) 0.0198(7) 0.0206(7) -0.0002(5) 0.0020(6) -0.0023(6) C16 0.0173(8) 0.0186(7) 0.0162(6) -0.0042(5) -0.0006(6) 0.0001(5) C17 0.0176(8) 0.0173(7) 0.0166(6) -0.0032(5) -0.0001(5) 0.0004(5) S17 0.0181(2) 0.0294(2) 0.02189(19) 0.00222(15) 0.00101(14) -0.00434(15) N17 0.0189(7) 0.0222(6) 0.0188(6) 0.0042(5) -0.0021(5) -0.0032(5) O16 0.0172(6) 0.0298(6) 0.0194(5) 0.0018(4) -0.0013(4) -0.0064(4) O1 0.0218(7) 0.0366(7) 0.0251(6) -0.0061(5) -0.0018(5) -0.0077(5) N18 0.0307(9) 0.0306(8) 0.0192(6) 0.0068(5) -0.0046(6) -0.0078(6) _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 C11 C12 1.409(2) . ? C11 C16 1.410(2) . ? C11 C17 1.4982(19) . ? C12 C13 1.383(2) . ? C13 C14 1.387(2) . ? C14 C15 1.383(2) . ? C15 C16 1.3998(19) . ? C16 O16 1.3623(17) . ? C17 N17 1.3289(19) . ? C17 S17 1.6853(15) . ? N17 N18 1.4187(16) . ? 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 C12 C11 C16 117.29(13) . . ? C12 C11 C17 117.85(13) . . ? C16 C11 C17 124.85(13) . . ? C13 C12 C11 122.08(15) . . ? C12 C13 C14 119.44(15) . . ? C15 C14 C13 120.34(14) . . ? C14 C15 C16 120.37(15) . . ? O16 C16 C15 120.05(14) . . ? O16 C16 C11 119.49(12) . . ? C15 C16 C11 120.46(14) . . ? N17 C17 C11 116.77(13) . . ? N17 C17 S17 120.38(11) . . ? C11 C17 S17 122.85(11) . . ? C17 N17 N18 123.73(13) . . ? 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 C16 C11 C12 C13 -0.1(2) . . . . ? C17 C11 C12 C13 179.71(14) . . . . ? C11 C12 C13 C14 1.1(2) . . . . ? C12 C13 C14 C15 -1.1(2) . . . . ? C13 C14 C15 C16 0.0(2) . . . . ? C14 C15 C16 O16 -179.40(13) . . . . ? C14 C15 C16 C11 1.1(2) . . . . ? C12 C11 C16 O16 179.45(13) . . . . ? C17 C11 C16 O16 -0.3(2) . . . . ? C12 C11 C16 C15 -1.1(2) . . . . ? C17 C11 C16 C15 179.18(13) . . . . ? C12 C11 C17 N17 -170.89(13) . . . . ? C16 C11 C17 N17 8.9(2) . . . . ? C12 C11 C17 S17 8.96(18) . . . . ? C16 C11 C17 S17 -171.28(11) . . . . ? C11 C17 N17 N18 178.62(12) . . . . ? S17 C17 N17 N18 -1.23(19) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.285 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.057 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; #===END