This journal is © The Owner Societies 2000 # CCDC Number: 1326/9 data_temp250K(1) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H25 N3 O7 S' _chemical_formula_weight 331.39 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 ? _symmetry_space_group_name_H-M ? 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 13.5030(10) _cell_length_b 8.4350(10) _cell_length_c 14.8390(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.240(10) _cell_angle_gamma 90.00 _cell_volume 1564.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.243 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9308 _exptl_absorpt_correction_T_max 0.9308 _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10793 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 29.08 _reflns_number_total 3766 _reflns_number_gt 3356 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0525P)^2^+0.4183P] 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 0.022(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3766 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0954 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.004 _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 O1 O 0.41644(7) -0.56016(12) 0.49713(7) 0.0388(2) Uani 1 d . . . O2 O 0.31870(7) -0.37645(11) 0.39249(7) 0.0345(2) Uani 1 d . . . N1 N 0.12340(7) -0.52796(11) 0.39265(7) 0.0238(2) Uani 1 d . . . C1 C 0.32885(9) -0.49628(14) 0.44107(8) 0.0254(2) Uani 1 d . . . C2 C 0.23432(8) -0.59479(14) 0.44207(9) 0.0272(2) Uani 1 d . . . C3 C 0.04785(10) -0.64413(17) 0.41007(11) 0.0362(3) Uani 1 d . . . C4 C 0.11305(10) -0.37185(16) 0.43654(10) 0.0343(3) Uani 1 d . . . C5 C 0.09282(11) -0.50951(19) 0.28514(9) 0.0362(3) Uani 1 d . . . H1O H 0.5000 -0.5000 0.5000 0.102(12) Uiso 1 d S . . H21 H 0.2372(13) -0.694(2) 0.4112(12) 0.046(4) Uiso 1 d . . . H22 H 0.2447(13) -0.610(2) 0.5094(13) 0.042(4) Uiso 1 d . . . H31 H -0.0264(13) -0.607(2) 0.3775(12) 0.043(4) Uiso 1 d . . . H32 H 0.0694(13) -0.653(2) 0.4812(12) 0.042(4) Uiso 1 d . . . H33 H 0.0602(14) -0.740(2) 0.3844(13) 0.049(5) Uiso 1 d . . . H41 H 0.1554(14) -0.296(2) 0.4190(12) 0.047(4) Uiso 1 d . . . H42 H 0.1355(13) -0.389(2) 0.5079(13) 0.044(4) Uiso 1 d . . . H43 H 0.0400(15) -0.338(2) 0.4081(13) 0.049(5) Uiso 1 d . . . H51 H 0.0154(15) -0.475(2) 0.2547(14) 0.047(5) Uiso 1 d . . . H52 H 0.1063(14) -0.609(2) 0.2582(13) 0.050(5) Uiso 1 d . . . H53 H 0.1371(14) -0.425(2) 0.2750(13) 0.046(5) Uiso 1 d . . . O3 O 0.08318(7) -0.02667(13) 0.56903(7) 0.0389(2) Uani 1 d . . . O4 O 0.18020(7) 0.01717(12) 0.47831(6) 0.0356(2) Uani 1 d . . . N2 N 0.37614(7) -0.02215(12) 0.65109(7) 0.0262(2) Uani 1 d . . . C6 C 0.17056(9) -0.00790(13) 0.55548(8) 0.0246(2) Uani 1 d . . . C7 C 0.26523(9) -0.01888(16) 0.65266(9) 0.0293(2) Uani 1 d . . . C8 C 0.39298(11) -0.16435(16) 0.59865(12) 0.0379(3) Uani 1 d . . . C9 C 0.40110(11) 0.12405(17) 0.60633(12) 0.0400(3) Uani 1 d . . . C10 C 0.45161(11) -0.0276(2) 0.75609(10) 0.0434(3) Uani 1 d . . . H3O H 0.0000 0.0000 0.5000 0.101(12) Uiso 1 d S . . H71 H 0.2582(13) -0.118(2) 0.6839(12) 0.041(4) Uiso 1 d . . . H72 H 0.2626(14) 0.070(2) 0.6891(13) 0.044(4) Uiso 1 d . . . H81 H 0.4689(14) -0.167(2) 0.6072(12) 0.046(4) Uiso 1 d . . . H82 H 0.3725(13) -0.250(2) 0.6272(12) 0.042(4) Uiso 1 d . . . H83 H 0.3510(14) -0.155(2) 0.5342(13) 0.045(4) Uiso 1 d . . . H91 H 0.3601(14) 0.119(2) 0.5383(14) 0.048(5) Uiso 1 d . . . H92 H 0.3835(15) 0.217(2) 0.6376(14) 0.059(5) Uiso 1 d . . . H93 H 0.4777(15) 0.120(2) 0.6167(13) 0.050(5) Uiso 1 d . . . H101 H 0.5209(16) -0.033(2) 0.7558(14) 0.051(5) Uiso 1 d . . . H102 H 0.4376(17) 0.073(3) 0.7887(16) 0.069(6) Uiso 1 d . . . H103 H 0.4342(14) -0.124(2) 0.7819(13) 0.050(5) Uiso 1 d . . . S1 S 0.24709(2) 0.05703(3) 0.23549(2) 0.02813(11) Uani 1 d . . . O1S O 0.28318(16) -0.0365(2) 0.17232(11) 0.0527(4) Uani 0.946(4) d P . . O2S O 0.33171(10) 0.15265(19) 0.30258(13) 0.0526(4) Uani 0.946(4) d P . . O3S O 0.15266(10) 0.14999(15) 0.18343(14) 0.0579(4) Uani 0.946(4) d P . . N1S N 0.20615(10) -0.07613(16) 0.29459(9) 0.0363(3) Uani 0.946(4) d P . . H1N H 0.2590(16) -0.149(2) 0.3181(14) 0.052(5) Uiso 1 d . . . H2N H 0.1976(17) -0.032(2) 0.3394(16) 0.059(6) Uiso 1 d . . . O1S' O 0.245(2) -0.055(4) 0.164(2) 0.049(8) Uiso 0.054(4) d P . . O2S' O 0.327(3) 0.182(5) 0.264(3) 0.085(13) Uiso 0.054(4) d P . . O3S' O 0.148(2) 0.123(3) 0.228(2) 0.050(6) Uiso 0.054(4) d P . . N1S' N 0.298(2) -0.034(3) 0.3423(19) 0.048(7) Uiso 0.054(4) d P . . 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 O1 0.0178(4) 0.0464(6) 0.0465(5) 0.0149(4) 0.0058(4) -0.0004(3) O2 0.0283(4) 0.0349(5) 0.0414(5) 0.0085(4) 0.0145(4) 0.0005(3) N1 0.0184(4) 0.0278(5) 0.0256(4) 0.0017(3) 0.0089(3) 0.0009(3) C1 0.0210(5) 0.0291(5) 0.0265(5) -0.0012(4) 0.0096(4) -0.0002(4) C2 0.0182(5) 0.0292(5) 0.0328(6) 0.0051(4) 0.0081(4) 0.0019(4) C3 0.0220(5) 0.0388(7) 0.0483(8) 0.0094(6) 0.0139(5) -0.0037(5) C4 0.0294(6) 0.0344(6) 0.0418(7) -0.0049(5) 0.0166(5) 0.0042(5) C5 0.0282(6) 0.0531(8) 0.0246(6) 0.0007(5) 0.0071(5) -0.0014(5) O3 0.0189(4) 0.0640(6) 0.0308(5) 0.0060(4) 0.0060(3) -0.0023(4) O4 0.0299(4) 0.0490(5) 0.0272(4) 0.0043(4) 0.0100(4) 0.0023(4) N2 0.0179(4) 0.0292(5) 0.0298(5) 0.0030(4) 0.0071(4) 0.0001(3) C6 0.0207(5) 0.0247(5) 0.0266(5) 0.0010(4) 0.0070(4) 0.0005(4) C7 0.0185(5) 0.0425(7) 0.0263(5) 0.0030(5) 0.0075(4) 0.0015(4) C8 0.0309(6) 0.0306(6) 0.0522(8) -0.0037(5) 0.0158(6) 0.0037(5) C9 0.0311(6) 0.0323(7) 0.0545(8) 0.0079(6) 0.0139(6) -0.0066(5) C10 0.0214(6) 0.0686(10) 0.0335(7) 0.0069(6) 0.0029(5) 0.0014(6) S1 0.02328(16) 0.03123(18) 0.02954(17) -0.00014(10) 0.00960(12) -0.00126(10) O1S 0.0571(10) 0.0691(9) 0.0432(7) -0.0133(6) 0.0319(7) -0.0029(8) O2S 0.0375(6) 0.0608(8) 0.0554(9) -0.0171(7) 0.0130(6) -0.0206(5) O3S 0.0354(6) 0.0451(7) 0.0798(11) 0.0223(7) 0.0066(6) 0.0079(5) N1S 0.0392(7) 0.0382(7) 0.0342(6) 0.0049(5) 0.0169(5) -0.0007(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 O1 C1 1.2793(14) . ? O2 C1 1.2187(15) . ? N1 C5 1.4970(15) . ? N1 C4 1.4989(16) . ? N1 C3 1.5057(15) . ? N1 C2 1.5058(13) . ? C1 C2 1.5278(15) . ? O3 C6 1.2796(14) . ? O4 C6 1.2191(14) . ? N2 C8 1.4933(16) . ? N2 C9 1.4983(16) . ? N2 C10 1.5055(16) . ? N2 C7 1.5069(14) . ? C6 C7 1.5253(16) . ? S1 O3S' 1.41(2) . ? S1 O1S' 1.41(3) . ? S1 O1S 1.4439(13) . ? S1 O2S 1.4443(12) . ? S1 O3S 1.4463(12) . ? S1 O2S' 1.46(4) . ? S1 N1S 1.6441(12) . ? S1 N1S' 1.66(3) . ? O1S O1S' 0.51(3) . ? O2S O2S' 0.61(4) . ? O2S N1S' 1.80(3) . ? O3S O3S' 0.72(3) . ? N1S N1S' 1.23(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 C5 N1 C4 109.77(10) . . ? C5 N1 C3 108.61(10) . . ? C4 N1 C3 108.44(10) . . ? C5 N1 C2 112.35(9) . . ? C4 N1 C2 110.88(9) . . ? C3 N1 C2 106.64(9) . . ? O2 C1 O1 127.11(11) . . ? O2 C1 C2 123.33(10) . . ? O1 C1 C2 109.56(10) . . ? N1 C2 C1 118.18(9) . . ? C8 N2 C9 109.02(11) . . ? C8 N2 C10 109.73(11) . . ? C9 N2 C10 107.84(11) . . ? C8 N2 C7 111.78(10) . . ? C9 N2 C7 112.55(10) . . ? C10 N2 C7 105.78(9) . . ? O4 C6 O3 127.00(11) . . ? O4 C6 C7 123.32(10) . . ? O3 C6 C7 109.67(10) . . ? N2 C7 C6 117.95(10) . . ? O3S' S1 O1S' 116.6(16) . . ? O3S' S1 O1S 134.7(10) . . ? O1S' S1 O1S 20.7(12) . . ? O3S' S1 O2S 108.4(10) . . ? O1S' S1 O2S 132.8(12) . . ? O1S S1 O2S 112.30(10) . . ? O3S' S1 O3S 29.2(12) . . ? O1S' S1 O3S 101.3(13) . . ? O1S S1 O3S 113.30(10) . . ? O2S S1 O3S 111.89(9) . . ? O3S' S1 O2S' 109(2) . . ? O1S' S1 O2S' 120(2) . . ? O1S S1 O2S' 100.7(17) . . ? O2S S1 O2S' 24.3(17) . . ? O3S S1 O2S' 99.8(17) . . ? O3S' S1 N1S 79.2(13) . . ? O1S' S1 N1S 91.5(13) . . ? O1S S1 N1S 103.71(9) . . ? O2S S1 N1S 110.60(9) . . ? O3S S1 N1S 104.41(8) . . ? O2S' S1 N1S 134.9(17) . . ? O3S' S1 N1S' 107.3(15) . . ? O1S' S1 N1S' 107.0(16) . . ? O1S S1 N1S' 104.4(9) . . ? O2S S1 N1S' 70.4(9) . . ? O3S S1 N1S' 136.4(9) . . ? O2S' S1 N1S' 93.8(19) . . ? N1S S1 N1S' 43.6(9) . . ? O1S' O1S S1 76(4) . . ? O2S' O2S S1 79(4) . . ? O2S' O2S N1S' 136(4) . . ? S1 O2S N1S' 60.3(9) . . ? O3S' O3S S1 73(2) . . ? N1S' N1S S1 68.8(12) . . ? O1S O1S' S1 83(4) . . ? O2S O2S' S1 77(4) . . ? O3S O3S' S1 78(2) . . ? N1S N1S' S1 67.6(12) . . ? N1S N1S' O2S 113.1(18) . . ? S1 N1S' O2S 49.2(7) . . ? 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 C5 N1 C2 C1 64.42(14) . . . . ? C4 N1 C2 C1 -58.83(13) . . . . ? C3 N1 C2 C1 -176.70(11) . . . . ? O2 C1 C2 N1 -9.41(17) . . . . ? O1 C1 C2 N1 171.15(10) . . . . ? C8 N2 C7 C6 -62.46(14) . . . . ? C9 N2 C7 C6 60.63(15) . . . . ? C10 N2 C7 C6 178.15(12) . . . . ? O4 C6 C7 N2 -9.01(18) . . . . ? O3 C6 C7 N2 171.84(11) . . . . ? O3S' S1 O1S O1S' -33(4) . . . . ? O2S S1 O1S O1S' 175(4) . . . . ? O3S S1 O1S O1S' -57(4) . . . . ? O2S' S1 O1S O1S' -163(4) . . . . ? N1S S1 O1S O1S' 55(4) . . . . ? N1S' S1 O1S O1S' 100(4) . . . . ? O3S' S1 O2S O2S' -95(5) . . . . ? O1S' S1 O2S O2S' 68(5) . . . . ? O1S S1 O2S O2S' 65(4) . . . . ? O3S S1 O2S O2S' -64(4) . . . . ? N1S S1 O2S O2S' -180(4) . . . . ? N1S' S1 O2S O2S' 163(4) . . . . ? O3S' S1 O2S N1S' 102.4(16) . . . . ? O1S' S1 O2S N1S' -95(2) . . . . ? O1S S1 O2S N1S' -98.0(10) . . . . ? O3S S1 O2S N1S' 133.2(10) . . . . ? O2S' S1 O2S N1S' -163(4) . . . . ? N1S S1 O2S N1S' 17.3(10) . . . . ? O1S' S1 O3S O3S' 125(3) . . . . ? O1S S1 O3S O3S' 143(2) . . . . ? O2S S1 O3S O3S' -89(2) . . . . ? O2S' S1 O3S O3S' -111(3) . . . . ? N1S S1 O3S O3S' 31(2) . . . . ? N1S' S1 O3S O3S' -5(3) . . . . ? O3S' S1 N1S N1S' -129.7(17) . . . . ? O1S' S1 N1S N1S' 113.5(18) . . . . ? O1S S1 N1S N1S' 96.6(13) . . . . ? O2S S1 N1S N1S' -24.0(13) . . . . ? O3S S1 N1S N1S' -144.5(13) . . . . ? O2S' S1 N1S N1S' -24(3) . . . . ? O3S' S1 O1S' O1S 154(3) . . . . ? O2S S1 O1S' O1S -7(5) . . . . ? O3S S1 O1S' O1S 128(3) . . . . ? O2S' S1 O1S' O1S 19(5) . . . . ? N1S S1 O1S' O1S -127(4) . . . . ? N1S' S1 O1S' O1S -86(4) . . . . ? N1S' O2S O2S' S1 21(5) . . . . ? O3S' S1 O2S' O2S 94(4) . . . . ? O1S' S1 O2S' O2S -128(4) . . . . ? O1S S1 O2S' O2S -121(4) . . . . ? O3S S1 O2S' O2S 122(4) . . . . ? N1S S1 O2S' O2S 0(6) . . . . ? N1S' S1 O2S' O2S -16(4) . . . . ? O1S' S1 O3S' O3S -63(3) . . . . ? O1S S1 O3S' O3S -51(3) . . . . ? O2S S1 O3S' O3S 102.2(18) . . . . ? O2S' S1 O3S' O3S 77(3) . . . . ? N1S S1 O3S' O3S -150(2) . . . . ? N1S' S1 O3S' O3S 176.7(18) . . . . ? S1 N1S N1S' O2S 19.4(10) . . . . ? O3S' S1 N1S' N1S 52.3(16) . . . . ? O1S' S1 N1S' N1S -73.6(17) . . . . ? O1S S1 N1S' N1S -94.9(10) . . . . ? O2S S1 N1S' N1S 156.2(13) . . . . ? O3S S1 N1S' N1S 54.6(17) . . . . ? O2S' S1 N1S' N1S 163(2) . . . . ? O3S' S1 N1S' O2S -103.9(11) . . . . ? O1S' S1 N1S' O2S 130.2(13) . . . . ? O1S S1 N1S' O2S 108.9(3) . . . . ? O3S S1 N1S' O2S -101.6(10) . . . . ? O2S' S1 N1S' O2S 6.9(18) . . . . ? N1S S1 N1S' O2S -156.2(13) . . . . ? O2S' O2S N1S' N1S -48(6) . . . . ? S1 O2S N1S' N1S -23.9(13) . . . . ? O2S' O2S N1S' S1 -24(6) . . . . ? _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 29.08 _diffrn_measured_fraction_theta_full 0.840 _refine_diff_density_max 0.312 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.044 data_temp100K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H25 N3 O7 S' _chemical_formula_weight 331.39 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 ? _symmetry_space_group_name_H-M ? 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 13.4670(10) _cell_length_b 8.3530(10) _cell_length_c 14.7010(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.000(10) _cell_angle_gamma 90.00 _cell_volume 1533.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9294 _exptl_absorpt_correction_T_max 0.9294 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10558 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 28.95 _reflns_number_total 3685 _reflns_number_gt 3385 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0440P)^2^+0.5786P] 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 0.0231(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3685 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41627(6) -0.56007(9) 0.49748(6) 0.01760(17) Uani 1 d . . . O2 O 0.31957(6) -0.37253(9) 0.39158(5) 0.01528(16) Uani 1 d . . . N1 N 0.12276(6) -0.52334(10) 0.39260(6) 0.01079(17) Uani 1 d . . . C1 C 0.32861(8) -0.49456(12) 0.44056(7) 0.01187(19) Uani 1 d . . . C2 C 0.23333(7) -0.59326(12) 0.44123(7) 0.01253(19) Uani 1 d . . . C3 C 0.04650(8) -0.63967(13) 0.41065(8) 0.0159(2) Uani 1 d . . . C4 C 0.11404(8) -0.36485(12) 0.43749(8) 0.0152(2) Uani 1 d . . . C5 C 0.09153(8) -0.50422(13) 0.28390(7) 0.0162(2) Uani 1 d . . . H1O H 0.5000 -0.5000 0.5000 0.074(10) Uiso 1 d S . . H21 H 0.2359(11) -0.6932(18) 0.4095(10) 0.023(3) Uiso 1 d . . . H22 H 0.2422(11) -0.6093(17) 0.5078(11) 0.019(3) Uiso 1 d . . . H31 H -0.0277(12) -0.5987(18) 0.3780(11) 0.023(4) Uiso 1 d . . . H32 H 0.0671(10) -0.6494(16) 0.4820(10) 0.016(3) Uiso 1 d . . . H33 H 0.0563(11) -0.7409(18) 0.3841(10) 0.021(3) Uiso 1 d . . . H41 H 0.1574(11) -0.2890(17) 0.4196(10) 0.019(3) Uiso 1 d . . . H42 H 0.1370(11) -0.3827(17) 0.5079(11) 0.021(3) Uiso 1 d . . . H43 H 0.0406(12) -0.3314(17) 0.4096(11) 0.022(3) Uiso 1 d . . . H51 H 0.0165(12) -0.4728(17) 0.2566(11) 0.017(3) Uiso 1 d . . . H52 H 0.1034(11) -0.6054(18) 0.2581(10) 0.019(3) Uiso 1 d . . . H53 H 0.1354(12) -0.4209(18) 0.2733(11) 0.022(3) Uiso 1 d . . . O3 O 0.08278(6) -0.02969(10) 0.56938(5) 0.01704(16) Uani 1 d . . . O4 O 0.18034(6) 0.02325(9) 0.47797(5) 0.01576(16) Uani 1 d . . . N2 N 0.37665(7) -0.01870(10) 0.65099(6) 0.01212(17) Uani 1 d . . . C6 C 0.17055(8) -0.00643(11) 0.55587(7) 0.01134(18) Uani 1 d . . . C7 C 0.26566(8) -0.01810(12) 0.65334(7) 0.01280(19) Uani 1 d . . . C8 C 0.39414(8) -0.16255(12) 0.59758(8) 0.0167(2) Uani 1 d . . . C9 C 0.40042(8) 0.13029(12) 0.60557(8) 0.0168(2) Uani 1 d . . . C10 C 0.45268(8) -0.02485(15) 0.75628(8) 0.0185(2) Uani 1 d . . . H3O H 0.0000 0.0000 0.5000 0.070(9) Uiso 1 d S . . H71 H 0.2608(11) -0.1166(17) 0.6857(10) 0.018(3) Uiso 1 d . . . H72 H 0.2623(11) 0.0722(17) 0.6906(10) 0.017(3) Uiso 1 d . . . H81 H 0.4687(12) -0.1627(17) 0.6053(10) 0.022(3) Uiso 1 d . . . H82 H 0.3755(11) -0.2543(17) 0.6248(10) 0.019(3) Uiso 1 d . . . H83 H 0.3508(11) -0.1502(17) 0.5307(11) 0.019(3) Uiso 1 d . . . H91 H 0.3589(11) 0.1274(17) 0.5383(11) 0.019(3) Uiso 1 d . . . H92 H 0.3832(11) 0.2219(18) 0.6366(10) 0.022(3) Uiso 1 d . . . H93 H 0.4754(12) 0.1264(17) 0.6161(10) 0.021(3) Uiso 1 d . . . H101 H 0.5223(12) -0.0306(17) 0.7575(11) 0.022(4) Uiso 1 d . . . H102 H 0.4405(12) 0.0724(18) 0.7885(11) 0.024(4) Uiso 1 d . . . H103 H 0.4358(11) -0.1199(18) 0.7844(11) 0.022(3) Uiso 1 d . . . S1 S 0.246028(18) 0.06031(3) 0.233082(17) 0.01203(9) Uani 1 d . . . O1S O 0.28239(7) -0.03690(10) 0.16946(6) 0.02247(18) Uani 1 d . . . O2S O 0.33139(6) 0.15820(10) 0.30103(6) 0.02168(18) Uani 1 d . . . O3S O 0.15113(6) 0.15529(10) 0.18039(6) 0.02362(19) Uani 1 d . . . N1S N 0.20515(7) -0.07342(11) 0.29419(7) 0.01616(18) Uani 1 d . . . H1N H 0.2569(12) -0.1492(19) 0.3185(11) 0.028(4) Uiso 1 d . . . H2N H 0.1926(13) -0.0289(19) 0.3412(12) 0.029(4) 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 O1 0.0085(3) 0.0206(4) 0.0210(4) 0.0064(3) 0.0024(3) -0.0001(3) O2 0.0138(3) 0.0149(3) 0.0175(4) 0.0027(3) 0.0063(3) 0.0003(3) N1 0.0085(4) 0.0122(4) 0.0113(4) 0.0007(3) 0.0034(3) 0.0000(3) C1 0.0100(4) 0.0139(4) 0.0119(4) -0.0020(3) 0.0043(3) -0.0007(3) C2 0.0083(4) 0.0131(4) 0.0151(5) 0.0021(3) 0.0031(3) 0.0009(3) C3 0.0105(4) 0.0167(5) 0.0209(5) 0.0035(4) 0.0064(4) -0.0020(4) C4 0.0139(4) 0.0146(5) 0.0180(5) -0.0022(4) 0.0069(4) 0.0017(4) C5 0.0142(5) 0.0228(5) 0.0102(4) 0.0010(4) 0.0031(4) -0.0005(4) O3 0.0089(3) 0.0263(4) 0.0143(3) 0.0025(3) 0.0025(3) -0.0010(3) O4 0.0147(3) 0.0195(4) 0.0126(3) 0.0014(3) 0.0046(3) 0.0005(3) N2 0.0091(4) 0.0127(4) 0.0134(4) 0.0009(3) 0.0029(3) 0.0001(3) C6 0.0100(4) 0.0095(4) 0.0129(4) -0.0001(3) 0.0025(3) 0.0005(3) C7 0.0082(4) 0.0172(5) 0.0122(4) 0.0008(4) 0.0028(4) 0.0005(3) C8 0.0143(5) 0.0131(5) 0.0227(5) -0.0021(4) 0.0068(4) 0.0019(4) C9 0.0140(5) 0.0132(5) 0.0226(5) 0.0032(4) 0.0060(4) -0.0022(4) C10 0.0095(5) 0.0284(6) 0.0139(5) 0.0023(4) 0.0002(4) 0.0008(4) S1 0.01013(13) 0.01316(14) 0.01205(13) 0.00011(8) 0.00330(9) -0.00050(8) O1S 0.0245(4) 0.0286(4) 0.0179(4) -0.0051(3) 0.0121(3) -0.0002(3) O2S 0.0162(4) 0.0233(4) 0.0227(4) -0.0060(3) 0.0040(3) -0.0074(3) O3S 0.0146(4) 0.0186(4) 0.0317(4) 0.0078(3) 0.0017(3) 0.0029(3) N1S 0.0179(4) 0.0165(4) 0.0155(4) 0.0027(3) 0.0079(3) 0.0001(3) _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 O1 C1 1.2857(12) . ? O2 C1 1.2275(12) . ? N1 C5 1.5008(13) . ? N1 C4 1.5033(13) . ? N1 C2 1.5073(12) . ? N1 C3 1.5079(12) . ? C1 C2 1.5283(13) . ? O3 C6 1.2846(12) . ? O4 C6 1.2262(12) . ? N2 C8 1.5015(13) . ? N2 C9 1.5025(13) . ? N2 C10 1.5032(13) . ? N2 C7 1.5080(12) . ? C6 C7 1.5259(13) . ? S1 O1S 1.4550(8) . ? S1 O3S 1.4564(8) . ? S1 O2S 1.4586(8) . ? S1 N1S 1.6518(9) . ? 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 C5 N1 C4 109.69(8) . . ? C5 N1 C2 112.29(8) . . ? C4 N1 C2 111.03(7) . . ? C5 N1 C3 108.56(8) . . ? C4 N1 C3 108.66(8) . . ? C2 N1 C3 106.49(7) . . ? O2 C1 O1 126.89(9) . . ? O2 C1 C2 123.56(9) . . ? O1 C1 C2 109.54(8) . . ? N1 C2 C1 118.07(8) . . ? C8 N2 C9 109.22(8) . . ? C8 N2 C10 109.35(8) . . ? C9 N2 C10 108.03(8) . . ? C8 N2 C7 111.45(8) . . ? C9 N2 C7 112.67(8) . . ? C10 N2 C7 105.98(8) . . ? O4 C6 O3 127.02(9) . . ? O4 C6 C7 122.95(9) . . ? O3 C6 C7 110.03(8) . . ? N2 C7 C6 117.99(8) . . ? O1S S1 O3S 113.68(5) . . ? O1S S1 O2S 112.61(5) . . ? O3S S1 O2S 111.61(5) . . ? O1S S1 N1S 103.49(5) . . ? O3S S1 N1S 104.65(5) . . ? O2S S1 N1S 110.14(5) . . ? 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 C5 N1 C2 C1 65.27(11) . . . . ? C4 N1 C2 C1 -57.94(11) . . . . ? C3 N1 C2 C1 -176.05(8) . . . . ? O2 C1 C2 N1 -10.34(14) . . . . ? O1 C1 C2 N1 170.13(8) . . . . ? C8 N2 C7 C6 -63.20(11) . . . . ? C9 N2 C7 C6 59.99(11) . . . . ? C10 N2 C7 C6 177.93(8) . . . . ? O4 C6 C7 N2 -9.80(14) . . . . ? O3 C6 C7 N2 171.09(8) . . . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 28.95 _diffrn_measured_fraction_theta_full 0.850 _refine_diff_density_max 0.415 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.052