# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email M.W.P.Bebbington@hw.ac.uk _publ_contact_author_name 'Magnus W. P. Bebbington' loop_ _publ_author_name M.Bebbington M.Higginbotham data_3875 _database_code_depnum_ccdc_archive 'CCDC 871548' #TrackingRef '3875.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H19 N O3 S' _chemical_formula_weight 245.33 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 P2(1)/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 19.8419(15) _cell_length_b 5.3049(4) _cell_length_c 11.5941(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.646(4) _cell_angle_gamma 90.00 _cell_volume 1220.31(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9945 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 31.92 _exptl_crystal_description BLOCK _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8689 _exptl_absorpt_correction_T_max 0.9406 _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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27110 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 32.06 _reflns_number_total 4215 _reflns_number_gt 3567 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0433P)^2^+0.4258P] 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 4215 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0890 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 S2 S 0.320635(12) 0.34640(4) 0.44768(2) 0.01261(7) Uani 1 1 d . . . O1 O 0.25051(3) 0.43253(14) 0.39533(6) 0.01360(14) Uani 1 1 d . . . O21 O 0.33369(4) 0.09257(14) 0.41062(6) 0.01763(15) Uani 1 1 d . . . O22 O 0.31749(4) 0.40121(15) 0.56772(6) 0.01800(15) Uani 1 1 d . . . N3 N 0.37619(4) 0.52882(17) 0.38835(7) 0.01372(16) Uani 1 1 d . . . H3 H 0.3740(7) 0.675(3) 0.4155(12) 0.016 Uiso 1 1 d . . . C4 C 0.37155(5) 0.53061(19) 0.25904(8) 0.01295(17) Uani 1 1 d . . . H4 H 0.3812 0.3571 0.2298 0.016 Uiso 1 1 calc R . . C5 C 0.30032(5) 0.60735(18) 0.21975(8) 0.01240(17) Uani 1 1 d . . . H5A H 0.2910 0.7812 0.2463 0.015 Uiso 1 1 calc R . . H5B H 0.2980 0.6067 0.1344 0.015 Uiso 1 1 calc R . . C6 C 0.24655(5) 0.43079(19) 0.26653(8) 0.01216(17) Uani 1 1 d . . . H6 H 0.2558 0.2560 0.2385 0.015 Uiso 1 1 calc R . . C7 C 0.17380(5) 0.49904(19) 0.23626(8) 0.01328(17) Uani 1 1 d . . . H7 H 0.1441 0.3811 0.2798 0.016 Uiso 1 1 calc R . . C8 C 0.15377(5) 0.7685(2) 0.27021(9) 0.01705(19) Uani 1 1 d . . . H8A H 0.1618 0.7931 0.3539 0.020 Uiso 1 1 calc R . . H8B H 0.1820 0.8909 0.2281 0.020 Uiso 1 1 calc R . . C9 C 0.07927(5) 0.8168(2) 0.24166(10) 0.0210(2) Uani 1 1 d . . . H9A H 0.0509 0.7030 0.2883 0.025 Uiso 1 1 calc R . . H9B H 0.0677 0.9927 0.2620 0.025 Uiso 1 1 calc R . . C10 C 0.06440(6) 0.7727(2) 0.11335(10) 0.0218(2) Uani 1 1 d . . . H10A H 0.0891 0.8986 0.0670 0.026 Uiso 1 1 calc R . . H10B H 0.0156 0.7953 0.0981 0.026 Uiso 1 1 calc R . . C11 C 0.08556(5) 0.5069(2) 0.07702(9) 0.0192(2) Uani 1 1 d . . . H11A H 0.0785 0.4873 -0.0072 0.023 Uiso 1 1 calc R . . H11B H 0.0569 0.3814 0.1164 0.023 Uiso 1 1 calc R . . C12 C 0.15973(5) 0.4561(2) 0.10716(9) 0.01681(19) Uani 1 1 d . . . H12A H 0.1887 0.5694 0.0614 0.020 Uiso 1 1 calc R . . H12B H 0.1711 0.2801 0.0868 0.020 Uiso 1 1 calc R . . C13 C 0.42387(5) 0.7082(2) 0.21350(9) 0.01658(19) Uani 1 1 d . . . H13 H 0.4249 0.8757 0.2425 0.020 Uiso 1 1 calc R . . C14 C 0.46860(6) 0.6434(3) 0.13513(10) 0.0244(2) Uani 1 1 d . . . H14A H 0.4712(8) 0.476(3) 0.1074(13) 0.029 Uiso 1 1 d . . . H14B H 0.5006(8) 0.763(3) 0.1032(13) 0.029 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 S2 0.01570(12) 0.01142(11) 0.01070(11) 0.00044(8) -0.00018(8) 0.00055(8) O1 0.0133(3) 0.0166(3) 0.0109(3) 0.0015(2) 0.0008(2) 0.0005(3) O21 0.0246(4) 0.0116(3) 0.0167(3) -0.0006(3) -0.0011(3) 0.0025(3) O22 0.0244(4) 0.0185(4) 0.0111(3) -0.0004(3) -0.0004(3) 0.0003(3) N3 0.0147(4) 0.0133(4) 0.0132(4) -0.0014(3) -0.0001(3) -0.0010(3) C4 0.0125(4) 0.0139(4) 0.0125(4) 0.0003(3) 0.0006(3) 0.0000(3) C5 0.0118(4) 0.0131(4) 0.0123(4) 0.0018(3) 0.0005(3) -0.0020(3) C6 0.0135(4) 0.0127(4) 0.0103(4) 0.0001(3) 0.0001(3) -0.0009(3) C7 0.0117(4) 0.0136(4) 0.0146(4) 0.0002(3) 0.0001(3) -0.0014(3) C8 0.0135(4) 0.0168(4) 0.0207(5) -0.0041(4) -0.0029(3) 0.0013(4) C9 0.0143(4) 0.0201(5) 0.0285(6) -0.0045(4) -0.0019(4) 0.0024(4) C10 0.0165(5) 0.0201(5) 0.0288(6) 0.0011(4) -0.0073(4) -0.0005(4) C11 0.0157(4) 0.0212(5) 0.0207(5) -0.0008(4) -0.0045(4) -0.0030(4) C12 0.0142(4) 0.0197(5) 0.0165(4) -0.0020(4) -0.0013(3) -0.0017(4) C13 0.0128(4) 0.0179(4) 0.0190(5) 0.0027(4) -0.0007(3) -0.0026(3) C14 0.0174(5) 0.0334(6) 0.0224(5) 0.0024(5) 0.0040(4) -0.0027(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 S2 O22 1.4238(8) . ? S2 O21 1.4379(8) . ? S2 O1 1.5792(7) . ? S2 N3 1.6254(9) . ? O1 C6 1.4946(11) . ? N3 C4 1.5011(12) . ? N3 H3 0.838(15) . ? C4 C13 1.5022(14) . ? C4 C5 1.5350(13) . ? C4 H4 1.0000 . ? C5 C6 1.5240(13) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5253(13) . ? C6 H6 1.0000 . ? C7 C8 1.5362(14) . ? C7 C12 1.5365(14) . ? C7 H7 1.0000 . ? C8 C9 1.5328(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5314(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5317(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5326(14) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.3228(15) . ? C13 H13 0.9500 . ? C14 H14A 0.947(17) . ? C14 H14B 0.973(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 O22 S2 O21 119.56(5) . . ? O22 S2 O1 105.57(4) . . ? O21 S2 O1 108.48(4) . . ? O22 S2 N3 109.24(5) . . ? O21 S2 N3 107.80(5) . . ? O1 S2 N3 105.30(4) . . ? C6 O1 S2 114.74(6) . . ? C4 N3 S2 113.10(6) . . ? C4 N3 H3 111.5(9) . . ? S2 N3 H3 110.7(10) . . ? N3 C4 C13 108.67(8) . . ? N3 C4 C5 110.12(7) . . ? C13 C4 C5 111.53(8) . . ? N3 C4 H4 108.8 . . ? C13 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C6 C5 C4 112.17(8) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? O1 C6 C5 108.82(7) . . ? O1 C6 C7 105.51(7) . . ? C5 C6 C7 115.90(8) . . ? O1 C6 H6 108.8 . . ? C5 C6 H6 108.8 . . ? C7 C6 H6 108.8 . . ? C6 C7 C8 114.13(8) . . ? C6 C7 C12 110.49(8) . . ? C8 C7 C12 110.05(8) . . ? C6 C7 H7 107.3 . . ? C8 C7 H7 107.3 . . ? C12 C7 H7 107.3 . . ? C9 C8 C7 110.61(8) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 111.04(9) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 110.95(9) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 111.38(9) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C7 111.07(8) . . ? C11 C12 H12A 109.4 . . ? C7 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C7 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C4 123.37(11) . . ? C14 C13 H13 118.3 . . ? C4 C13 H13 118.3 . . ? C13 C14 H14A 121.1(9) . . ? C13 C14 H14B 122.5(9) . . ? H14A C14 H14B 116.4(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 O22 S2 O1 C6 170.61(6) . . . . ? O21 S2 O1 C6 -60.10(7) . . . . ? N3 S2 O1 C6 55.09(7) . . . . ? O22 S2 N3 C4 -166.05(7) . . . . ? O21 S2 N3 C4 62.59(8) . . . . ? O1 S2 N3 C4 -53.07(7) . . . . ? S2 N3 C4 C13 178.83(7) . . . . ? S2 N3 C4 C5 56.40(9) . . . . ? N3 C4 C5 C6 -58.54(10) . . . . ? C13 C4 C5 C6 -179.27(8) . . . . ? S2 O1 C6 C5 -59.39(9) . . . . ? S2 O1 C6 C7 175.62(6) . . . . ? C4 C5 C6 O1 58.77(10) . . . . ? C4 C5 C6 C7 177.42(8) . . . . ? O1 C6 C7 C8 65.82(10) . . . . ? C5 C6 C7 C8 -54.64(11) . . . . ? O1 C6 C7 C12 -169.54(8) . . . . ? C5 C6 C7 C12 70.00(11) . . . . ? C6 C7 C8 C9 -177.47(9) . . . . ? C12 C7 C8 C9 57.66(11) . . . . ? C7 C8 C9 C10 -57.46(12) . . . . ? C8 C9 C10 C11 55.82(12) . . . . ? C9 C10 C11 C12 -54.98(12) . . . . ? C10 C11 C12 C7 55.83(12) . . . . ? C6 C7 C12 C11 176.18(8) . . . . ? C8 C7 C12 C11 -56.89(11) . . . . ? N3 C4 C13 C14 126.83(11) . . . . ? C5 C4 C13 C14 -111.59(12) . . . . ? 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 N3 H3 O21 0.838(15) 2.356(15) 3.1188(12) 151.7(13) 1_565 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.662 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.055