# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Luo, Jiangshui' 'Hu, Jin' 'Saak, Wolfgang' 'Beckhaus, Ruediger' 'Wittstock, Gunther' 'Vankelecom, Ivo' 'Agert, Carsten' 'Conrad, Olaf' _publ_contact_author_name 'Olaf Conrad' _publ_contact_author_address ; ; _publ_contact_author_email Olaf.Conrad@next-energy.de data_TRAMS12 _database_code_depnum_ccdc_archive 'CCDC 804598' #TrackingRef '- TRAMS12.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H7 N3 O3 S' _chemical_formula_weight 165.18 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 P21/c 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 5.4497(4) _cell_length_b 7.4823(7) _cell_length_c 16.7814(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.212(8) _cell_angle_gamma 90.00 _cell_volume 681.45(10) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3078 _cell_measurement_theta_min 6.0 _cell_measurement_theta_max 56.6 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.427 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9008 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'imaging plate' _diffrn_measurement_method phi-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7990 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 28.30 _reflns_number_total 1608 _reflns_number_gt 1143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (Stoe, 1999)' _computing_cell_refinement 'IPDS (Stoe, 1999)' _computing_data_reduction 'XRED (Stoe, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0299P)^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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1608 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0574 _refine_ls_wR_factor_gt 0.0540 _refine_ls_goodness_of_fit_ref 0.881 _refine_ls_restrained_S_all 0.881 _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 0.55310(7) 0.19130(5) 0.35107(2) 0.01875(11) Uani 1 1 d . . . O1 O 0.7970(2) 0.25278(16) 0.33628(6) 0.0283(3) Uani 1 1 d . . . O2 O 0.4240(2) 0.10073(14) 0.28152(6) 0.0261(3) Uani 1 1 d . . . O3 O 0.5564(2) 0.07926(15) 0.42294(6) 0.0277(3) Uani 1 1 d . . . C1 C 0.3756(4) 0.3814(2) 0.36919(11) 0.0277(4) Uani 1 1 d . . . H3A H 0.454(4) 0.439(3) 0.4163(13) 0.033 Uiso 1 1 d . . . H3B H 0.373(4) 0.461(3) 0.3214(12) 0.033 Uiso 1 1 d . . . H3C H 0.210(4) 0.346(3) 0.3765(11) 0.033 Uiso 1 1 d . . . N1 N 0.1248(3) 0.21419(18) 0.15327(8) 0.0239(3) Uani 1 1 d . . . H1N H 0.224(4) 0.176(2) 0.1915(12) 0.029 Uiso 1 1 d . . . N2 N 0.1615(3) 0.1770(2) 0.07520(7) 0.0285(3) Uani 1 1 d . . . N3 N -0.1670(3) 0.34496(17) 0.08401(8) 0.0229(3) Uani 1 1 d . . . H3N H -0.290(4) 0.402(3) 0.0723(12) 0.027 Uiso 1 1 d . . . C2 C -0.0209(3) 0.2594(2) 0.03500(10) 0.0268(4) Uani 1 1 d . . . H2 H -0.048(4) 0.257(2) -0.0191(13) 0.032(5) Uiso 1 1 d . . . C3 C -0.0687(3) 0.3146(2) 0.15833(9) 0.0237(3) Uani 1 1 d . . . H3 H -0.131(4) 0.354(2) 0.2037(11) 0.028 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 S1 0.0179(2) 0.02496(17) 0.01289(16) 0.00187(15) -0.00144(11) -0.00342(16) O1 0.0189(7) 0.0431(7) 0.0228(6) 0.0066(4) 0.0018(4) -0.0014(5) O2 0.0315(8) 0.0281(6) 0.0171(5) -0.0019(4) -0.0075(4) 0.0019(5) O3 0.0311(7) 0.0331(6) 0.0171(5) 0.0069(4) -0.0066(4) -0.0123(5) C1 0.0230(11) 0.0290(8) 0.0317(9) -0.0039(7) 0.0056(7) -0.0062(7) N1 0.0253(8) 0.0288(7) 0.0162(6) 0.0030(5) -0.0055(5) 0.0041(6) N2 0.0289(9) 0.0362(8) 0.0198(6) -0.0010(6) -0.0011(5) 0.0114(6) N3 0.0201(8) 0.0262(7) 0.0218(6) 0.0016(5) -0.0014(5) 0.0068(5) C2 0.0293(11) 0.0341(8) 0.0161(7) -0.0004(6) -0.0021(6) 0.0083(7) C3 0.0270(9) 0.0259(7) 0.0181(7) -0.0004(6) 0.0012(6) 0.0025(7) _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 O1 1.4491(12) . ? S1 O3 1.4677(11) . ? S1 O2 1.4721(11) . ? S1 C1 1.7624(18) . ? C1 H3A 0.96(2) . ? C1 H3B 1.00(2) . ? C1 H3C 0.96(2) . ? N1 C3 1.304(2) . ? N1 N2 1.3716(18) . ? N1 H1N 0.85(2) . ? N2 C2 1.304(2) . ? N3 C3 1.331(2) . ? N3 C2 1.356(2) . ? N3 H3N 0.81(2) . ? C2 H2 0.91(2) . ? C3 H3 0.909(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 O1 S1 O3 112.28(7) . . ? O1 S1 O2 112.95(7) . . ? O3 S1 O2 110.97(6) . . ? O1 S1 C1 107.44(8) . . ? O3 S1 C1 106.57(8) . . ? O2 S1 C1 106.15(8) . . ? S1 C1 H3A 107.0(12) . . ? S1 C1 H3B 108.2(11) . . ? H3A C1 H3B 111.5(16) . . ? S1 C1 H3C 109.6(12) . . ? H3A C1 H3C 111.7(16) . . ? H3B C1 H3C 108.8(17) . . ? C3 N1 N2 111.60(13) . . ? C3 N1 H1N 127.3(13) . . ? N2 N1 H1N 121.0(13) . . ? C2 N2 N1 103.16(13) . . ? C3 N3 C2 106.20(14) . . ? C3 N3 H3N 125.1(14) . . ? C2 N3 H3N 128.7(14) . . ? N2 C2 N3 111.81(14) . . ? N2 C2 H2 123.6(13) . . ? N3 C2 H2 124.6(13) . . ? N1 C3 N3 107.23(13) . . ? N1 C3 H3 127.2(12) . . ? N3 C3 H3 125.5(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 C3 N1 N2 C2 -0.47(19) . . . . ? N1 N2 C2 N3 0.04(19) . . . . ? C3 N3 C2 N2 0.4(2) . . . . ? N2 N1 C3 N3 0.73(19) . . . . ? C2 N3 C3 N1 -0.67(19) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.297 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.052