data_syk03 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H30 N2 O7 S' _chemical_formula_sum 'C27 H30 N2 O7 S' _chemical_formula_weight 526.59 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 Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 9.5308(8) _cell_length_b 9.7901(9) _cell_length_c 13.8253(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.914(2) _cell_angle_gamma 90.00 _cell_volume 1266.67(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9727 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 33.11 _exptl_crystal_description Blade _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9436 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details ? _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 SMART 1000' _diffrn_measurement_method '\w scans at 5 \f settings' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17354 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 33.37 _reflns_number_total 6630 _reflns_number_gt 5764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v5.630' _computing_cell_refinement 'Bruker SAINT v6.45A' _computing_data_reduction 'Bruker SAINT v6.45A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP v5.1' _computing_publication_material 'Bruker XCIF v6.12' _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 matrix' _refine_ls_weighting_scheme Sigma _refine_ls_weighting_details 'w=1/s^2^(Fo^2^)' _atom_sites_solution_primary 'Direct methods' _atom_sites_solution_secondary 'Difference Fourier map' _atom_sites_solution_hydrogens 'Geometric positions' _refine_ls_hydrogen_treatment Riding _chemical_absolute_configuration ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(5) _refine_ls_number_reflns 6630 _refine_ls_number_parameters 339 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0785 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.413 _refine_ls_restrained_S_all 1.413 _refine_ls_shift/su_max 0.003 _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 0.25606(5) 0.41661(4) 0.59006(4) 0.01982(11) Uani 1 1 d . . . O1 O 0.10905(15) 0.38678(14) 0.59006(11) 0.0276(3) Uani 1 1 d . . . O2 O 0.35434(15) 0.30410(13) 0.58877(10) 0.0261(3) Uani 1 1 d . . . O3 O 0.59531(14) 0.98146(13) 0.66123(10) 0.0228(3) Uani 1 1 d . . . O4 O 0.75897(14) 0.76523(14) 0.81682(10) 0.0248(3) Uani 1 1 d . . . O5 O 0.72144(14) 0.94995(13) 0.90438(10) 0.0221(3) Uani 1 1 d . . . O6 O 0.43872(14) 1.03983(13) 0.87315(10) 0.0212(3) Uani 1 1 d . . . O7 O 0.36292(13) 0.85577(13) 0.94566(10) 0.0190(3) Uani 1 1 d . . . N1 N 0.31537(17) 0.50907(15) 0.68683(12) 0.0175(3) Uani 1 1 d . . . N2 N 0.35549(16) 1.02035(15) 0.65581(12) 0.0180(3) Uani 1 1 d . . . H2 H 0.3499 1.1044 0.6328 0.022 Uiso 1 1 calc R . . C1 C 0.2669(2) 0.51581(18) 0.48492(15) 0.0172(4) Uani 1 1 d . . . C2 C 0.3664(2) 0.48371(19) 0.42842(15) 0.0208(4) Uani 1 1 d . . . H2A H 0.4320 0.4110 0.4471 0.025 Uiso 1 1 calc R . . C3 C 0.3700(2) 0.55894(19) 0.34362(16) 0.0227(4) Uani 1 1 d . . . H3 H 0.4382 0.5365 0.3042 0.027 Uiso 1 1 calc R . . C4 C 0.2753(2) 0.66695(18) 0.31527(15) 0.0208(4) Uani 1 1 d . . . C5 C 0.1775(2) 0.69932(19) 0.37574(16) 0.0239(4) Uani 1 1 d . . . H5 H 0.1138 0.7739 0.3587 0.029 Uiso 1 1 calc R . . C6 C 0.1722(2) 0.6249(2) 0.45951(16) 0.0224(4) Uani 1 1 d . . . H6 H 0.1049 0.6475 0.4997 0.027 Uiso 1 1 calc R . . C7 C 0.2775(3) 0.7430(2) 0.22131(17) 0.0327(5) Uani 1 1 d . . . H7A H 0.3623 0.7165 0.1953 0.049 Uiso 1 1 calc R . . H7B H 0.2802 0.8415 0.2343 0.049 Uiso 1 1 calc R . . H7C H 0.1914 0.7208 0.1729 0.049 Uiso 1 1 calc R . . C8 C 0.4669(2) 0.54809(18) 0.70498(15) 0.0188(4) Uani 1 1 d . . . H8A H 0.5200 0.4795 0.6735 0.023 Uiso 1 1 calc R . . H8B H 0.5041 0.5444 0.7768 0.023 Uiso 1 1 calc R . . C9 C 0.49876(19) 0.68984(18) 0.66754(15) 0.0172(4) Uani 1 1 d . . . H9A H 0.4547 0.6965 0.5969 0.021 Uiso 1 1 calc R . . H9B H 0.6034 0.6991 0.6729 0.021 Uiso 1 1 calc R . . C10 C 0.44506(19) 0.80920(18) 0.72235(14) 0.0148(4) Uani 1 1 d . . . C11 C 0.28341(19) 0.81557(17) 0.71045(13) 0.0148(4) Uani 1 1 d . . . C12 C 0.18225(19) 0.71842(17) 0.72416(13) 0.0146(4) Uani 1 1 d . . . C13 C 0.21583(18) 0.56828(17) 0.74681(14) 0.0155(4) Uani 1 1 d . . . H13 H 0.1234 0.5182 0.7270 0.019 Uiso 1 1 calc R . . C14 C 0.26525(19) 0.54087(18) 0.85582(15) 0.0184(4) Uani 1 1 d . . . H14 H 0.3091 0.6136 0.8959 0.022 Uiso 1 1 calc R . . C15 C 0.25104(19) 0.4205(2) 0.89932(16) 0.0227(4) Uani 1 1 d . . . C16 C 0.1948(2) 0.2934(2) 0.84542(18) 0.0323(5) Uani 1 1 d . . . H16A H 0.1488 0.3168 0.7779 0.048 Uiso 1 1 calc R . . H16B H 0.1248 0.2502 0.8792 0.048 Uiso 1 1 calc R . . H16C H 0.2739 0.2300 0.8438 0.048 Uiso 1 1 calc R . . C17 C 0.2943(2) 0.4057(3) 1.00881(18) 0.0367(6) Uani 1 1 d . . . H17A H 0.3413 0.4897 1.0367 0.055 Uiso 1 1 calc R . . H17B H 0.3607 0.3288 1.0239 0.055 Uiso 1 1 calc R . . H17C H 0.2094 0.3888 1.0374 0.055 Uiso 1 1 calc R . . C18 C 0.04042(19) 0.76098(19) 0.71303(14) 0.0170(4) Uani 1 1 d . . . H18 H -0.0299 0.6975 0.7247 0.020 Uiso 1 1 calc R . . C19 C -0.0010(2) 0.89382(19) 0.68528(14) 0.0190(4) Uani 1 1 d . . . H19 H -0.0978 0.9204 0.6813 0.023 Uiso 1 1 calc R . . C20 C 0.0980(2) 0.98876(19) 0.66320(14) 0.0181(4) Uani 1 1 d . . . H20 H 0.0700 1.0781 0.6405 0.022 Uiso 1 1 calc R . . C21 C 0.23850(19) 0.94614(17) 0.67609(13) 0.0152(4) Uani 1 1 d . . . C22 C 0.4787(2) 0.94678(18) 0.67592(14) 0.0177(4) Uani 1 1 d . . . C23 C 0.51914(19) 0.81487(18) 0.83546(13) 0.0156(4) Uani 1 1 d . . . H23 H 0.5056 0.7234 0.8645 0.019 Uiso 1 1 calc R . . C24 C 0.6788(2) 0.83989(18) 0.84927(14) 0.0181(4) Uani 1 1 d . . . C25 C 0.8742(2) 0.9752(2) 0.92119(16) 0.0267(5) Uani 1 1 d . . . H25A H 0.9244 0.9021 0.9623 0.040 Uiso 1 1 calc R . . H25B H 0.8951 1.0631 0.9547 0.040 Uiso 1 1 calc R . . H25C H 0.9062 0.9774 0.8579 0.040 Uiso 1 1 calc R . . C26 C 0.43923(18) 0.91882(19) 0.88672(14) 0.0152(4) Uani 1 1 d . . . C27 C 0.2603(2) 0.9418(2) 0.98169(16) 0.0252(4) Uani 1 1 d . . . H27A H 0.3087 1.0230 1.0133 0.038 Uiso 1 1 calc R . . H27B H 0.2172 0.8908 1.0297 0.038 Uiso 1 1 calc R . . H27C H 0.1854 0.9697 0.9264 0.038 Uiso 1 1 calc R . . 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 0.0284(3) 0.0091(2) 0.0237(3) -0.0005(2) 0.0094(2) -0.0026(2) O1 0.0333(8) 0.0219(7) 0.0297(9) -0.0067(6) 0.0115(7) -0.0105(6) O2 0.0421(9) 0.0099(6) 0.0292(8) 0.0025(6) 0.0140(7) 0.0025(6) O3 0.0230(7) 0.0208(7) 0.0267(8) 0.0036(6) 0.0097(6) -0.0055(6) O4 0.0187(7) 0.0262(7) 0.0301(9) 0.0001(6) 0.0061(6) 0.0054(6) O5 0.0167(7) 0.0267(7) 0.0229(8) -0.0024(6) 0.0036(6) -0.0009(5) O6 0.0212(7) 0.0155(7) 0.0276(8) -0.0007(6) 0.0063(6) 0.0011(5) O7 0.0199(7) 0.0208(7) 0.0180(7) 0.0020(5) 0.0078(5) 0.0010(5) N1 0.0208(8) 0.0126(8) 0.0211(9) -0.0007(6) 0.0088(6) 0.0004(6) N2 0.0222(9) 0.0096(7) 0.0224(9) 0.0048(6) 0.0046(7) -0.0003(6) C1 0.0230(10) 0.0101(8) 0.0185(10) -0.0008(7) 0.0038(8) -0.0049(7) C2 0.0201(10) 0.0138(9) 0.0284(12) -0.0018(8) 0.0041(8) 0.0015(7) C3 0.0239(11) 0.0185(10) 0.0280(12) -0.0013(8) 0.0109(9) 0.0000(7) C4 0.0235(10) 0.0133(9) 0.0252(11) 0.0012(8) 0.0034(8) -0.0012(7) C5 0.0241(10) 0.0157(9) 0.0309(12) 0.0012(8) 0.0025(8) 0.0047(8) C6 0.0230(11) 0.0164(10) 0.0292(12) -0.0033(8) 0.0084(9) 0.0010(8) C7 0.0399(13) 0.0255(11) 0.0324(13) 0.0085(10) 0.0058(10) 0.0033(10) C8 0.0196(10) 0.0139(9) 0.0246(11) -0.0004(7) 0.0082(8) 0.0025(7) C9 0.0172(10) 0.0165(9) 0.0189(10) 0.0003(7) 0.0060(7) 0.0004(7) C10 0.0164(9) 0.0124(8) 0.0167(10) 0.0021(7) 0.0054(7) -0.0009(6) C11 0.0192(9) 0.0133(9) 0.0127(9) -0.0019(7) 0.0052(7) 0.0009(7) C12 0.0194(9) 0.0132(9) 0.0117(9) 0.0009(7) 0.0042(7) 0.0009(7) C13 0.0139(9) 0.0134(9) 0.0213(10) -0.0013(7) 0.0089(8) -0.0022(7) C14 0.0151(9) 0.0169(9) 0.0240(11) 0.0033(8) 0.0059(8) 0.0001(7) C15 0.0146(9) 0.0252(10) 0.0302(12) 0.0115(9) 0.0093(8) 0.0048(8) C16 0.0328(12) 0.0154(10) 0.0524(16) 0.0127(10) 0.0173(11) 0.0049(8) C17 0.0283(12) 0.0474(14) 0.0361(14) 0.0223(11) 0.0103(10) -0.0017(10) C18 0.0185(10) 0.0177(9) 0.0151(10) -0.0008(7) 0.0042(8) -0.0033(7) C19 0.0167(9) 0.0221(10) 0.0172(10) -0.0008(8) 0.0010(8) 0.0059(7) C20 0.0229(10) 0.0141(9) 0.0167(10) 0.0025(7) 0.0020(8) 0.0050(7) C21 0.0225(10) 0.0128(9) 0.0107(9) -0.0001(7) 0.0038(8) -0.0001(7) C22 0.0251(10) 0.0130(9) 0.0152(10) 0.0001(7) 0.0042(8) -0.0025(7) C23 0.0177(9) 0.0105(8) 0.0192(10) 0.0030(7) 0.0050(8) 0.0012(7) C24 0.0186(10) 0.0179(9) 0.0179(10) 0.0064(8) 0.0037(8) 0.0010(7) C25 0.0173(10) 0.0374(12) 0.0244(12) -0.0017(9) 0.0012(8) -0.0073(8) C26 0.0097(8) 0.0196(9) 0.0151(10) -0.0006(7) -0.0008(7) -0.0009(7) C27 0.0231(10) 0.0306(11) 0.0241(11) -0.0009(9) 0.0104(9) 0.0037(8) _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 1.4313(14) . ? S1 O2 1.4482(14) . ? S1 N1 1.6255(17) . ? S1 C1 1.767(2) . ? O3 C22 1.215(2) . ? O4 C24 1.204(2) . ? O5 C24 1.338(2) . ? O5 C25 1.451(2) . ? O6 C26 1.199(2) . ? O7 C26 1.341(2) . ? O7 C27 1.449(2) . ? N1 C8 1.469(2) . ? N1 C13 1.491(2) . ? N2 C22 1.361(2) . ? N2 C21 1.403(2) . ? C1 C2 1.374(3) . ? C1 C6 1.400(3) . ? C2 C3 1.390(3) . ? C3 C4 1.398(3) . ? C4 C5 1.401(3) . ? C4 C7 1.501(3) . ? C5 C6 1.377(3) . ? C8 C9 1.531(2) . ? C9 C10 1.532(2) . ? C10 C11 1.519(3) . ? C10 C22 1.551(2) . ? C10 C23 1.590(2) . ? C11 C12 1.393(2) . ? C11 C21 1.402(2) . ? C12 C18 1.395(2) . ? C12 C13 1.524(2) . ? C13 C14 1.515(3) . ? C14 C15 1.341(3) . ? C15 C16 1.496(3) . ? C15 C17 1.499(3) . ? C18 C19 1.392(3) . ? C19 C20 1.398(3) . ? C20 C21 1.382(3) . ? C23 C24 1.517(2) . ? C23 C26 1.524(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 O1 S1 O2 118.70(9) . . ? O1 S1 N1 107.55(8) . . ? O2 S1 N1 107.99(8) . . ? O1 S1 C1 108.78(9) . . ? O2 S1 C1 105.60(9) . . ? N1 S1 C1 107.79(8) . . ? C24 O5 C25 114.58(15) . . ? C26 O7 C27 114.87(15) . . ? C8 N1 C13 120.84(15) . . ? C8 N1 S1 117.58(12) . . ? C13 N1 S1 121.04(13) . . ? C22 N2 C21 111.90(15) . . ? C2 C1 C6 120.90(18) . . ? C2 C1 S1 119.74(14) . . ? C6 C1 S1 119.35(16) . . ? C1 C2 C3 119.21(17) . . ? C2 C3 C4 121.30(19) . . ? C3 C4 C5 118.11(18) . . ? C3 C4 C7 120.25(18) . . ? C5 C4 C7 121.62(17) . . ? C6 C5 C4 121.13(18) . . ? C5 C6 C1 119.32(19) . . ? N1 C8 C9 115.42(15) . . ? C8 C9 C10 114.69(15) . . ? C11 C10 C9 113.86(15) . . ? C11 C10 C22 101.80(14) . . ? C9 C10 C22 110.06(14) . . ? C11 C10 C23 110.93(14) . . ? C9 C10 C23 112.65(14) . . ? C22 C10 C23 106.77(14) . . ? C12 C11 C21 119.60(16) . . ? C12 C11 C10 132.16(16) . . ? C21 C11 C10 108.20(15) . . ? C11 C12 C18 117.54(16) . . ? C11 C12 C13 124.25(16) . . ? C18 C12 C13 118.17(15) . . ? N1 C13 C14 111.94(14) . . ? N1 C13 C12 113.07(14) . . ? C14 C13 C12 112.87(15) . . ? C15 C14 C13 124.25(18) . . ? C14 C15 C16 124.3(2) . . ? C14 C15 C17 120.4(2) . . ? C16 C15 C17 115.24(18) . . ? C19 C18 C12 121.84(17) . . ? C18 C19 C20 120.92(17) . . ? C21 C20 C19 116.63(16) . . ? C20 C21 C11 123.04(17) . . ? C20 C21 N2 127.26(16) . . ? C11 C21 N2 109.68(16) . . ? O3 C22 N2 126.81(16) . . ? O3 C22 C10 125.37(16) . . ? N2 C22 C10 107.82(15) . . ? C24 C23 C26 114.28(15) . . ? C24 C23 C10 112.17(14) . . ? C26 C23 C10 108.22(14) . . ? O4 C24 O5 123.72(18) . . ? O4 C24 C23 123.19(17) . . ? O5 C24 C23 113.04(15) . . ? O6 C26 O7 124.28(17) . . ? O6 C26 C23 125.06(17) . . ? O7 C26 C23 110.58(15) . . ? 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 N2 H2 O2 0.88 2.05 2.928(2) 174.5 1_565 _diffrn_measured_fraction_theta_max 0.792 _diffrn_reflns_theta_full 33.37 _diffrn_measured_fraction_theta_full 0.792 _refine_diff_density_max 0.698 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.058