Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_s92 _database_code_CSD 160088 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Hursthouse, Michael B.' 'Kilburn, J. D.' 'Kyne, Graham M.' 'Light, Mark E.' 'Mendoza, Javier de' _publ_contact_author_name 'Dr J D Kilburn' _publ_contact_author_address ; Dr J D Kilburn Department of Chemistry University of Southampton Southampton Hants SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email 'J.D.KILBURN@SOTON.AC.UK' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H32 N6 O2 S' _chemical_formula_weight 456.61 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4566(3) _cell_length_b 10.7149(4) _cell_length_c 13.2326(4) _cell_angle_alpha 89.975(2) _cell_angle_beta 79.123(2) _cell_angle_gamma 65.1932(12) _cell_volume 1190.56(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4737 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 26.36 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.9672 _exptl_absorpt_correction_T_max 0.9917 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappac CCD' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18090 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 26.36 _reflns_number_total 4737 _reflns_number_gt 3975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT and DENZO' _computing_cell_refinement 'DENZO & SCALEPACK' _computing_data_reduction 'DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON' _computing_publication_material 'WINGX' _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 w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.8702P] 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 SHELXL _refine_ls_extinction_coef 0.034(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4737 _refine_ls_number_parameters 418 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.72083(6) 0.10694(5) 0.40123(4) 0.03051(15) Uani 1 d . . . O2 O 1.35620(15) 0.50588(13) 0.33828(10) 0.0266(3) Uani 1 d . . . N5 N 1.02594(17) 0.42400(15) 0.34957(11) 0.0222(3) Uani 1 d . . . O1 O 0.15813(17) 0.60678(15) 0.96759(11) 0.0385(4) Uani 1 d . . . N6 N 1.15029(19) 0.58644(16) 0.25466(12) 0.0261(3) Uani 1 d . . . N4 N 0.69807(18) 0.35471(16) 0.46105(12) 0.0248(3) Uani 1 d . . . N2 N 0.38835(17) 0.34157(15) 0.76433(11) 0.0226(3) Uani 1 d . . . N1 N 0.37059(18) 0.57952(16) 0.84151(12) 0.0253(3) Uani 1 d . . . N3 N 0.57049(18) 0.26331(16) 0.57841(12) 0.0261(3) Uani 1 d . . . C6 C 0.2790(2) 0.40159(19) 0.85211(13) 0.0238(4) Uani 1 d . . . C7 C 0.1834(2) 0.3430(2) 0.90267(15) 0.0289(4) Uani 1 d . . . C18 C 1.1666(2) 0.40938(17) 0.36880(13) 0.0220(4) Uani 1 d . . . C14 C 0.9656(2) 0.33872(18) 0.39153(13) 0.0229(4) Uani 1 d . . . C19 C 1.2321(2) 0.50563(17) 0.31896(13) 0.0222(4) Uani 1 d . . . C11 C 0.5246(2) 0.15931(19) 0.62401(14) 0.0251(4) Uani 1 d . . . C5 C 0.2638(2) 0.53935(19) 0.89282(14) 0.0254(4) Uani 1 d . . . C10 C 0.4032(2) 0.22151(18) 0.72386(13) 0.0231(4) Uani 1 d . . . C17 C 1.2513(2) 0.31223(19) 0.42915(15) 0.0275(4) Uani 1 d . . . C12 C 0.6614(2) 0.24731(18) 0.48385(13) 0.0218(4) Uani 1 d . . . C16 C 1.1882(2) 0.2230(2) 0.47141(16) 0.0309(4) Uani 1 d . . . C13 C 0.8067(2) 0.3591(2) 0.36956(14) 0.0267(4) Uani 1 d . . . C20 C 1.1903(2) 0.69156(19) 0.20328(15) 0.0262(4) Uani 1 d . . . C15 C 1.0452(2) 0.23597(19) 0.45225(15) 0.0273(4) Uani 1 d . . . C8 C 0.2016(2) 0.2170(2) 0.86103(15) 0.0313(4) Uani 1 d . . . C21 C 1.1152(2) 0.8280(2) 0.26959(15) 0.0281(4) Uani 1 d . . . C9 C 0.3120(2) 0.1550(2) 0.77079(15) 0.0281(4) Uani 1 d . . . C22 C 1.1520(3) 0.9403(2) 0.21636(17) 0.0326(4) Uani 1 d . . . C3 C 0.4824(2) 0.6994(2) 0.94101(16) 0.0294(4) Uani 1 d . . . C4 C 0.3748(2) 0.70987(19) 0.86643(15) 0.0279(4) Uani 1 d . . . C23 C 1.0669(3) 0.9924(2) 0.12762(19) 0.0410(5) Uani 1 d . . . C2 C 0.5057(3) 0.8314(2) 0.95156(17) 0.0347(5) Uani 1 d . . . C1 C 0.6228(4) 0.8424(3) 0.8612(2) 0.0551(7) Uani 1 d . . . H20A H 1.157(2) 0.697(2) 0.1367(16) 0.028(5) Uiso 1 d . . . H15 H 0.999(2) 0.177(2) 0.4793(15) 0.027(5) Uiso 1 d . . . H13B H 0.823(2) 0.283(2) 0.3183(15) 0.024(5) Uiso 1 d . . . H17 H 1.346(3) 0.307(2) 0.4398(16) 0.031(5) Uiso 1 d . . . H11B H 0.478(2) 0.126(2) 0.5763(16) 0.027(5) Uiso 1 d . . . H13A H 0.759(2) 0.446(2) 0.3396(16) 0.029(5) Uiso 1 d . . . H20B H 1.309(3) 0.653(2) 0.1902(16) 0.031(5) Uiso 1 d . . . H11A H 0.619(3) 0.078(2) 0.6397(16) 0.033(6) Uiso 1 d . . . H4A H 0.264(3) 0.779(2) 0.8969(16) 0.034(6) Uiso 1 d . . . H21B H 1.001(3) 0.857(2) 0.2887(16) 0.033(6) Uiso 1 d . . . H4B H 0.412(3) 0.739(2) 0.7986(17) 0.035(6) Uiso 1 d . . . H3B H 0.588(3) 0.620(2) 0.9140(18) 0.042(6) Uiso 1 d . . . H21A H 1.157(2) 0.812(2) 0.3359(17) 0.033(6) Uiso 1 d . . . H22A H 1.270(3) 0.904(2) 0.1897(17) 0.039(6) Uiso 1 d . . . H1N H 0.437(2) 0.525(2) 0.7894(17) 0.027(5) Uiso 1 d . . . H8 H 0.137(3) 0.170(2) 0.8951(17) 0.039(6) Uiso 1 d . . . H9 H 0.329(3) 0.067(2) 0.7350(17) 0.038(6) Uiso 1 d . . . H2B H 0.542(3) 0.832(3) 1.017(2) 0.048(7) Uiso 1 d . . . H23C H 0.949(3) 1.028(3) 0.153(2) 0.059(8) Uiso 1 d . . . H7 H 0.107(3) 0.390(2) 0.9654(17) 0.031(5) Uiso 1 d . . . H2A H 0.406(3) 0.909(2) 0.9589(17) 0.036(6) Uiso 1 d . . . H16 H 1.247(3) 0.151(2) 0.5159(18) 0.045(6) Uiso 1 d . . . H23A H 1.089(3) 1.072(3) 0.0970(19) 0.051(7) Uiso 1 d . . . H6N H 1.065(3) 0.578(2) 0.2495(17) 0.038(6) Uiso 1 d . . . H23B H 1.100(3) 0.918(3) 0.071(2) 0.050(7) Uiso 1 d . . . H1C H 0.731(4) 0.768(3) 0.854(2) 0.067(9) Uiso 1 d . . . H1B H 0.640(3) 0.921(3) 0.870(2) 0.059(8) Uiso 1 d . . . H22B H 1.123(3) 1.020(3) 0.266(2) 0.057(7) Uiso 1 d . . . H3A H 0.435(3) 0.676(2) 1.0084(19) 0.042(6) Uiso 1 d . . . H1A H 0.592(3) 0.833(3) 0.795(2) 0.062(8) Uiso 1 d . . . HN4 H 0.672(2) 0.416(2) 0.5110(17) 0.028(5) Uiso 1 d . . . HN3 H 0.553(3) 0.333(2) 0.6196(18) 0.038(6) Uiso 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 0.0378(3) 0.0246(3) 0.0261(3) -0.00341(18) 0.0014(2) -0.0138(2) O2 0.0257(7) 0.0299(7) 0.0275(7) 0.0012(5) -0.0036(5) -0.0160(6) N5 0.0225(7) 0.0237(8) 0.0210(7) 0.0013(6) -0.0023(6) -0.0114(6) O1 0.0353(8) 0.0405(8) 0.0354(8) -0.0131(6) 0.0091(6) -0.0189(7) N6 0.0243(8) 0.0264(8) 0.0308(9) 0.0066(6) -0.0059(7) -0.0138(7) N4 0.0241(8) 0.0257(8) 0.0258(8) -0.0014(7) -0.0009(6) -0.0135(6) N2 0.0213(7) 0.0254(8) 0.0226(8) 0.0007(6) -0.0035(6) -0.0118(6) N1 0.0244(8) 0.0251(8) 0.0258(8) -0.0035(6) -0.0014(7) -0.0117(6) N3 0.0293(8) 0.0255(8) 0.0248(8) -0.0045(6) 0.0021(7) -0.0162(7) C6 0.0213(8) 0.0272(9) 0.0236(9) 0.0016(7) -0.0044(7) -0.0111(7) C7 0.0246(9) 0.0351(11) 0.0272(10) 0.0009(8) -0.0007(8) -0.0149(8) C18 0.0225(9) 0.0199(8) 0.0221(9) -0.0011(7) -0.0007(7) -0.0093(7) C14 0.0250(9) 0.0236(9) 0.0202(8) 0.0009(7) -0.0018(7) -0.0117(7) C19 0.0225(9) 0.0218(9) 0.0211(8) -0.0031(7) 0.0006(7) -0.0104(7) C11 0.0286(10) 0.0235(9) 0.0255(9) 0.0011(7) -0.0032(8) -0.0144(8) C5 0.0229(9) 0.0291(10) 0.0236(9) -0.0007(7) -0.0032(7) -0.0111(7) C10 0.0222(9) 0.0245(9) 0.0247(9) 0.0022(7) -0.0065(7) -0.0112(7) C17 0.0240(9) 0.0277(10) 0.0326(10) 0.0044(8) -0.0079(8) -0.0120(8) C12 0.0182(8) 0.0222(9) 0.0252(9) 0.0025(7) -0.0058(7) -0.0084(7) C16 0.0288(10) 0.0292(10) 0.0362(11) 0.0116(8) -0.0109(9) -0.0121(8) C13 0.0266(9) 0.0318(10) 0.0263(9) 0.0074(8) -0.0066(8) -0.0164(8) C20 0.0261(10) 0.0257(10) 0.0269(10) 0.0061(7) -0.0022(8) -0.0126(8) C15 0.0306(10) 0.0246(9) 0.0296(10) 0.0072(8) -0.0052(8) -0.0150(8) C8 0.0289(10) 0.0384(11) 0.0336(10) 0.0061(8) -0.0034(8) -0.0224(9) C21 0.0297(10) 0.0278(10) 0.0271(10) 0.0041(8) -0.0040(8) -0.0135(8) C9 0.0302(10) 0.0295(10) 0.0306(10) 0.0022(8) -0.0069(8) -0.0182(8) C22 0.0362(11) 0.0277(10) 0.0383(11) 0.0059(9) -0.0080(9) -0.0176(9) C3 0.0319(10) 0.0293(10) 0.0298(10) 0.0005(8) -0.0070(9) -0.0154(9) C4 0.0290(10) 0.0239(9) 0.0311(10) -0.0003(8) -0.0060(8) -0.0115(8) C23 0.0428(13) 0.0368(12) 0.0471(14) 0.0172(11) -0.0132(11) -0.0190(10) C2 0.0330(11) 0.0307(11) 0.0403(12) -0.0089(9) -0.0052(9) -0.0147(9) C1 0.0569(17) 0.0486(15) 0.0670(19) -0.0135(13) 0.0101(14) -0.0390(14) _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 C12 1.6833(18) . ? O2 C19 1.248(2) . ? N5 C14 1.337(2) . ? N5 C18 1.346(2) . ? O1 C5 1.233(2) . ? N6 C19 1.326(2) . ? N6 C20 1.461(2) . ? N4 C12 1.353(2) . ? N4 C13 1.447(2) . ? N2 C10 1.335(2) . ? N2 C6 1.349(2) . ? N1 C5 1.331(2) . ? N1 C4 1.454(2) . ? N3 C12 1.343(2) . ? N3 C11 1.449(2) . ? C6 C7 1.381(3) . ? C6 C5 1.511(3) . ? C7 C8 1.388(3) . ? C18 C17 1.380(3) . ? C18 C19 1.505(2) . ? C14 C15 1.399(3) . ? C14 C13 1.510(3) . ? C11 C10 1.515(2) . ? C10 C9 1.396(2) . ? C17 C16 1.391(3) . ? C16 C15 1.373(3) . ? C20 C21 1.518(3) . ? C8 C9 1.380(3) . ? C21 C22 1.525(3) . ? C22 C23 1.522(3) . ? C3 C4 1.518(3) . ? C3 C2 1.529(3) . ? C2 C1 1.510(3) . ? 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 C14 N5 C18 117.67(15) . . ? C19 N6 C20 123.56(16) . . ? C12 N4 C13 125.59(16) . . ? C10 N2 C6 118.65(15) . . ? C5 N1 C4 123.72(16) . . ? C12 N3 C11 124.64(16) . . ? N2 C6 C7 122.72(17) . . ? N2 C6 C5 116.47(15) . . ? C7 C6 C5 120.80(16) . . ? C6 C7 C8 118.22(17) . . ? N5 C18 C17 123.95(16) . . ? N5 C18 C19 116.20(15) . . ? C17 C18 C19 119.85(16) . . ? N5 C14 C15 121.96(16) . . ? N5 C14 C13 116.33(16) . . ? C15 C14 C13 121.72(16) . . ? O2 C19 N6 123.91(16) . . ? O2 C19 C18 120.52(16) . . ? N6 C19 C18 115.57(15) . . ? N3 C11 C10 109.40(15) . . ? O1 C5 N1 124.41(17) . . ? O1 C5 C6 120.76(16) . . ? N1 C5 C6 114.83(15) . . ? N2 C10 C9 122.08(16) . . ? N2 C10 C11 116.95(15) . . ? C9 C10 C11 120.97(16) . . ? C18 C17 C16 117.86(17) . . ? N3 C12 N4 113.92(16) . . ? N3 C12 S1 122.57(13) . . ? N4 C12 S1 123.50(14) . . ? C15 C16 C17 119.00(18) . . ? N4 C13 C14 112.33(15) . . ? N6 C20 C21 112.00(15) . . ? C16 C15 C14 119.55(17) . . ? C9 C8 C7 119.67(17) . . ? C20 C21 C22 112.90(16) . . ? C8 C9 C10 118.64(18) . . ? C23 C22 C21 113.45(17) . . ? C4 C3 C2 111.88(17) . . ? N1 C4 C3 113.38(16) . . ? C1 C2 C3 112.69(18) . . ? 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 N1 H1N N2 0.86(2) 2.23(2) 2.674(2) 111.5(16) . N1 H1N O2 0.86(2) 2.24(2) 2.978(2) 144.3(18) 2_766 N6 H6N N5 0.86(2) 2.23(2) 2.674(2) 112.4(18) . N4 HN4 O2 0.85(2) 2.09(2) 2.897(2) 157.5(19) 2_766 N3 HN3 N2 0.86(2) 2.20(2) 2.629(2) 110.4(18) . N3 HN3 O2 0.86(2) 2.34(2) 3.089(2) 145.9(19) 2_766 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.244 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.046