# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email a.white@imperial.ac.uk _publ_contact_author_name 'Andrew J.P. White' loop_ _publ_author_name 'Donald Craig' 'John W. Harvey' "Alexander G. O'Brien" data_syn-15a _database_code_depnum_ccdc_archive 'CCDC 813338' #TrackingRef 'Angew 02-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H25 N3 O2 S' _chemical_formula_sum 'C17 H25 N3 O2 S' _chemical_formula_weight 335.46 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' 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)/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 5.48411(17) _cell_length_b 8.0007(2) _cell_length_c 41.2338(12) _cell_angle_alpha 90 _cell_angle_beta 90.353(3) _cell_angle_gamma 90 _cell_volume 1809.17(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6701 _cell_measurement_theta_min 3.8494 _cell_measurement_theta_max 31.5858 _exptl_crystal_description 'platy needles' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88234 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur 3' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 15.9863 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22930 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_sigmaI/netI 0.0776 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -59 _diffrn_reflns_limit_l_max 59 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 31.68 _reflns_number_total 5800 _reflns_number_gt 4035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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^)+(0.0135P)^2^+5.1905P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5800 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1493 _refine_ls_R_factor_gt 0.1083 _refine_ls_wR_factor_ref 0.2018 _refine_ls_wR_factor_gt 0.1913 _refine_ls_goodness_of_fit_ref 1.212 _refine_ls_restrained_S_all 1.212 _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 C1 C 0.5159(6) -0.0146(4) 0.15884(8) 0.0239(7) Uani 1 1 d . . . H1A H 0.5417 -0.1161 0.1722 0.029 Uiso 1 1 calc R . . H1B H 0.3388 0.0095 0.1585 0.029 Uiso 1 1 calc R . . C2 C 0.6017(6) -0.0499(4) 0.12376(8) 0.0245(7) Uani 1 1 d . . . H2A H 0.7834 -0.0606 0.1242 0.029 Uiso 1 1 calc R . . C3 C 0.5363(6) 0.0918(4) 0.10031(8) 0.0235(7) Uani 1 1 d . . . H3A H 0.6031 0.1993 0.1090 0.028 Uiso 1 1 calc R . . C4 C 0.6385(7) 0.0615(5) 0.06652(8) 0.0304(8) Uani 1 1 d . . . H4A H 0.8144 0.0356 0.0685 0.037 Uiso 1 1 calc R . . H4B H 0.5571 -0.0379 0.0571 0.037 Uiso 1 1 calc R . . C5 C 0.6073(8) 0.2066(5) 0.04335(9) 0.0363(9) Uani 1 1 d . . . H5A H 0.6550 0.3115 0.0545 0.044 Uiso 1 1 calc R . . H5B H 0.4334 0.2161 0.0370 0.044 Uiso 1 1 calc R . . C6 C 0.7626(8) 0.1851(5) 0.01265(9) 0.0382(9) Uani 1 1 d . . . H6A H 0.9361 0.1766 0.0192 0.046 Uiso 1 1 calc R . . H6B H 0.7169 0.0784 0.0021 0.046 Uiso 1 1 calc R . . C7 C 0.7373(8) 0.3232(6) -0.01168(10) 0.0450(10) Uani 1 1 d . . . H7A H 0.7700 0.4314 -0.0009 0.054 Uiso 1 1 calc R . . H7B H 0.5674 0.3255 -0.0199 0.054 Uiso 1 1 calc R . . C8 C 0.9096(9) 0.3032(7) -0.04000(10) 0.0515(12) Uani 1 1 d . . . H8A H 0.8867 0.3963 -0.0552 0.077 Uiso 1 1 calc R . . H8B H 0.8752 0.1975 -0.0511 0.077 Uiso 1 1 calc R . . H8C H 1.0783 0.3028 -0.0320 0.077 Uiso 1 1 calc R . . S9 S 0.67085(16) 0.15531(12) 0.17726(2) 0.02560(19) Uani 1 1 d . . . O10 O 0.9281(5) 0.1230(4) 0.17519(6) 0.0404(7) Uani 1 1 d . . . O11 O 0.5781(5) 0.3088(3) 0.16432(6) 0.0355(6) Uani 1 1 d . . . C12 C 0.5857(6) 0.1439(4) 0.21843(7) 0.0218(6) Uani 1 1 d . . . C13 C 0.3718(6) 0.2186(4) 0.22854(8) 0.0256(7) Uani 1 1 d . . . H13A H 0.2670 0.2722 0.2134 0.031 Uiso 1 1 calc R . . C14 C 0.3126(6) 0.2139(5) 0.26118(8) 0.0290(8) Uani 1 1 d . . . H14A H 0.1672 0.2663 0.2684 0.035 Uiso 1 1 calc R . . C15 C 0.4632(6) 0.1334(4) 0.28361(8) 0.0261(7) Uani 1 1 d . . . C16 C 0.6742(7) 0.0585(4) 0.27273(8) 0.0290(8) Uani 1 1 d . . . H16A H 0.7779 0.0034 0.2879 0.035 Uiso 1 1 calc R . . C17 C 0.7388(6) 0.0619(5) 0.24013(8) 0.0282(7) Uani 1 1 d . . . H17A H 0.8840 0.0094 0.2329 0.034 Uiso 1 1 calc R . . C18 C 0.3978(8) 0.1284(6) 0.31932(9) 0.0415(10) Uani 1 1 d . . . H18A H 0.4972 0.0437 0.3303 0.062 Uiso 1 1 calc R . . H18B H 0.2248 0.1004 0.3216 0.062 Uiso 1 1 calc R . . H18C H 0.4291 0.2381 0.3291 0.062 Uiso 1 1 calc R . . C19 C 0.4982(7) -0.2153(5) 0.11325(8) 0.0318(8) Uani 1 1 d . . . H19A H 0.3263 -0.2242 0.1110 0.038 Uiso 1 1 calc R . . C20 C 0.6296(9) -0.3479(6) 0.10706(11) 0.0492(11) Uani 1 1 d . . . H20A H 0.8021 -0.3432 0.1091 0.059 Uiso 1 1 calc R . . H20B H 0.5525 -0.4488 0.1005 0.059 Uiso 1 1 calc R . . N21 N 0.2639(5) 0.1031(4) 0.09861(8) 0.0323(7) Uani 1 1 d . . . N22 N 0.1798(6) 0.2434(5) 0.10268(8) 0.0384(8) Uani 1 1 d . . . N23 N 0.0818(8) 0.3658(6) 0.10625(12) 0.0658(13) Uani 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 C1 0.0263(17) 0.0207(16) 0.0248(15) -0.0037(13) 0.0019(13) -0.0052(13) C2 0.0232(16) 0.0251(17) 0.0253(16) -0.0046(13) 0.0008(13) 0.0022(14) C3 0.0201(15) 0.0235(16) 0.0271(16) -0.0029(13) 0.0028(12) 0.0010(13) C4 0.0310(19) 0.034(2) 0.0266(16) -0.0060(15) 0.0030(14) 0.0008(16) C5 0.043(2) 0.038(2) 0.0280(18) -0.0024(16) 0.0039(16) 0.0024(18) C6 0.047(2) 0.040(2) 0.0273(17) -0.0028(16) 0.0037(16) 0.0061(19) C7 0.051(3) 0.047(3) 0.037(2) 0.0009(19) 0.0063(18) 0.005(2) C8 0.054(3) 0.063(3) 0.038(2) 0.002(2) 0.012(2) -0.001(2) S9 0.0264(4) 0.0283(4) 0.0221(4) -0.0036(3) 0.0015(3) -0.0046(4) O10 0.0253(13) 0.065(2) 0.0308(13) -0.0082(13) 0.0039(10) -0.0087(13) O11 0.0558(18) 0.0235(13) 0.0270(12) 0.0004(10) 0.0006(12) -0.0036(12) C12 0.0213(15) 0.0230(16) 0.0212(14) -0.0029(13) 0.0016(11) -0.0040(13) C13 0.0211(16) 0.0269(17) 0.0286(17) -0.0011(14) -0.0041(13) -0.0005(14) C14 0.0237(17) 0.0307(18) 0.0325(18) -0.0072(15) 0.0044(14) 0.0017(15) C15 0.0313(18) 0.0223(17) 0.0245(15) -0.0011(13) 0.0034(13) -0.0043(14) C16 0.0347(19) 0.0254(17) 0.0269(16) 0.0040(14) -0.0029(14) 0.0065(15) C17 0.0257(17) 0.0296(18) 0.0293(17) 0.0000(14) 0.0026(14) 0.0093(15) C18 0.056(3) 0.044(2) 0.0245(17) -0.0013(17) 0.0077(17) 0.005(2) C19 0.037(2) 0.0301(19) 0.0280(17) -0.0059(15) 0.0015(15) 0.0000(16) C20 0.067(3) 0.030(2) 0.051(2) -0.005(2) 0.003(2) -0.005(2) N21 0.0214(15) 0.0321(17) 0.0434(18) -0.0030(14) 0.0004(13) 0.0052(13) N22 0.0267(17) 0.044(2) 0.0443(19) 0.0092(16) 0.0042(14) 0.0080(15) N23 0.049(2) 0.049(3) 0.100(4) 0.014(2) 0.014(2) 0.023(2) _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 C1 C2 1.550(4) . ? C1 S9 1.772(3) . ? C2 C19 1.502(5) . ? C2 C3 1.531(5) . ? C3 N21 1.498(4) . ? C3 C4 1.524(5) . ? C4 C5 1.513(5) . ? C5 C6 1.539(5) . ? C6 C7 1.498(6) . ? C7 C8 1.515(6) . ? S9 O11 1.431(3) . ? S9 O10 1.438(3) . ? S9 C12 1.766(3) . ? C12 C13 1.383(5) . ? C12 C17 1.388(5) . ? C13 C14 1.387(5) . ? C14 C15 1.394(5) . ? C15 C16 1.380(5) . ? C15 C18 1.518(5) . ? C16 C17 1.393(5) . ? C19 C20 1.308(6) . ? N21 N22 1.225(5) . ? N22 N23 1.128(5) . ? 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 C2 C1 S9 113.1(2) . . ? C19 C2 C3 112.6(3) . . ? C19 C2 C1 108.3(3) . . ? C3 C2 C1 112.5(3) . . ? N21 C3 C4 109.8(3) . . ? N21 C3 C2 107.7(3) . . ? C4 C3 C2 111.9(3) . . ? C5 C4 C3 114.5(3) . . ? C4 C5 C6 111.9(3) . . ? C7 C6 C5 114.7(3) . . ? C6 C7 C8 112.5(4) . . ? O11 S9 O10 118.62(18) . . ? O11 S9 C12 107.89(16) . . ? O10 S9 C12 108.26(15) . . ? O11 S9 C1 109.27(16) . . ? O10 S9 C1 107.75(17) . . ? C12 S9 C1 104.11(16) . . ? C13 C12 C17 121.4(3) . . ? C13 C12 S9 119.8(3) . . ? C17 C12 S9 118.8(3) . . ? C12 C13 C14 119.0(3) . . ? C13 C14 C15 121.0(3) . . ? C16 C15 C14 118.6(3) . . ? C16 C15 C18 120.5(3) . . ? C14 C15 C18 120.9(3) . . ? C15 C16 C17 121.6(3) . . ? C12 C17 C16 118.4(3) . . ? C20 C19 C2 124.3(4) . . ? N22 N21 C3 115.1(3) . . ? N23 N22 N21 173.6(4) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.450 _refine_diff_density_min -0.793 _refine_diff_density_rms 0.075 #===END