data_cb005 _publ_contact_author_name 'Dr Christopher D. Bray' _publ_contact_author_address ;School of Biological and Chemical Sciences The Joseph Priestley Building Queen Mary University of London MIle End Road London E1 4NS ; _publ_contact_author_email c.bray@qmul.ac.uk _publ_contact_author_phone '+44 (0)20 7882 3271' _publ_contact_author_fax '+44 (0)20 7882 7427' loop_ _publ_author_name _publ_author_address 'Bray, Christopher D.' ;School of Biological and Chemical Sciences The Joseph Priestley Building Queen Mary University of London MIle End Road London E1 4NS ; 'De Faveri, Giorgio' ;School of Biological and Chemical Sciences The Joseph Priestley Building Queen Mary University of London MIle End Road London E1 4NS ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 O3 S' _chemical_formula_weight 302.37 _chemical_absolute_configuration rm 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' 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.5094(8) _cell_length_b 8.0322(12) _cell_length_c 34.254(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1515.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 15286 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 5445 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_av_sigmaI/netI 0.1050 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 24.40 _reflns_number_total 2290 _reflns_number_gt 1772 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0000P)^2^+6.9691P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_number_reflns 2290 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1181 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.1899 _refine_ls_wR_factor_gt 0.1719 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 0.4303(12) 0.6076(9) 0.9541(2) 0.0223(16) Uani 1 1 d . . . H1 H 0.2531 0.6334 0.9522 0.027 Uiso 1 1 calc R . . C2 C 0.4983(16) 0.4229(10) 0.9581(2) 0.036(2) Uani 1 1 d . . . H2 H 0.6557 0.3896 0.9459 0.044 Uiso 1 1 calc R . . C3 C 0.5180(16) 0.5377(9) 0.99299(19) 0.033(2) Uani 1 1 d . . . H3A H 0.6827 0.5693 1.0019 0.040 Uiso 1 1 calc R . . H3B H 0.3970 0.5247 1.0141 0.040 Uiso 1 1 calc R . . C4 C 0.2943(17) 0.3023(10) 0.9533(2) 0.042(2) Uani 1 1 d . . . H4A H 0.3440 0.1907 0.9626 0.051 Uiso 1 1 calc R . . H4B H 0.1522 0.3389 0.9687 0.051 Uiso 1 1 calc R . . C5 C 0.0637(13) 0.1652(9) 0.9042(2) 0.0274(18) Uani 1 1 d . . . H5A H -0.0963 0.1916 0.9158 0.033 Uiso 1 1 calc R . . H5B H 0.1210 0.0587 0.9155 0.033 Uiso 1 1 calc R . . C6 C 0.0394(13) 0.1485(9) 0.8607(2) 0.0269(18) Uani 1 1 d . . . C7 C 0.2129(14) 0.2123(9) 0.8355(2) 0.0308(19) Uani 1 1 d . . . H7 H 0.3478 0.2717 0.8457 0.037 Uiso 1 1 calc R . . C8 C 0.1911(14) 0.1902(10) 0.7955(2) 0.036(2) Uani 1 1 d . . . H8 H 0.3098 0.2357 0.7784 0.044 Uiso 1 1 calc R . . C9 C -0.0048(15) 0.1011(11) 0.7802(2) 0.035(2) Uani 1 1 d . . . H9 H -0.0183 0.0819 0.7529 0.042 Uiso 1 1 calc R . . C10 C -0.1781(15) 0.0416(10) 0.8056(2) 0.036(2) Uani 1 1 d . . . H10 H -0.3138 -0.0176 0.7957 0.043 Uiso 1 1 calc R . . C11 C -0.1584(14) 0.0662(9) 0.8450(2) 0.0334(19) Uani 1 1 d . . . H11 H -0.2824 0.0262 0.8618 0.040 Uiso 1 1 calc R . . C12 C 0.5794(13) 0.6816(9) 0.8789(2) 0.0288(18) Uani 1 1 d . . . C13 C 0.7391(14) 0.5690(9) 0.8613(2) 0.0268(17) Uani 1 1 d . . . H13 H 0.8694 0.5214 0.8756 0.032 Uiso 1 1 calc R . . C14 C 0.7024(15) 0.5283(9) 0.8222(2) 0.034(2) Uani 1 1 d . . . H14 H 0.8121 0.4553 0.8093 0.041 Uiso 1 1 calc R . . C15 C 0.5046(16) 0.5944(10) 0.8017(2) 0.036(2) Uani 1 1 d . . . H15 H 0.4806 0.5665 0.7750 0.043 Uiso 1 1 calc R . . C16 C 0.3423(15) 0.7015(10) 0.8206(2) 0.035(2) Uani 1 1 d . . . H16 H 0.2071 0.7454 0.8068 0.043 Uiso 1 1 calc R . . C17 C 0.3774(13) 0.7434(10) 0.8589(2) 0.0281(16) Uani 1 1 d . . . H17 H 0.2650 0.8141 0.8718 0.034 Uiso 1 1 calc R . . O1 O 0.8722(9) 0.6963(7) 0.93802(15) 0.0388(14) Uani 1 1 d . . . O2 O 0.5426(10) 0.9086(6) 0.93355(15) 0.0355(14) Uani 1 1 d . . . O3 O 0.2328(11) 0.2949(6) 0.91313(14) 0.0377(14) Uani 1 1 d . . . S1 S 0.6238(3) 0.7364(2) 0.92823(6) 0.0297(5) 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 0.006(3) 0.028(4) 0.034(4) -0.004(3) -0.005(3) -0.003(3) C2 0.039(5) 0.028(4) 0.043(5) 0.005(4) 0.000(4) 0.007(4) C3 0.046(5) 0.034(5) 0.020(4) -0.007(3) 0.004(4) 0.012(4) C4 0.064(6) 0.022(5) 0.040(5) -0.004(4) -0.009(4) -0.009(4) C5 0.021(4) 0.021(4) 0.040(4) 0.012(3) -0.003(3) 0.003(3) C6 0.021(4) 0.025(4) 0.035(4) -0.002(3) 0.002(3) 0.007(3) C7 0.027(4) 0.026(5) 0.040(4) -0.004(3) 0.004(3) 0.001(4) C8 0.031(5) 0.036(5) 0.042(5) -0.002(4) 0.003(4) -0.005(4) C9 0.040(5) 0.040(5) 0.026(4) -0.003(4) -0.009(4) 0.010(4) C10 0.036(5) 0.035(5) 0.036(5) 0.004(4) -0.008(4) -0.007(4) C11 0.024(4) 0.028(5) 0.048(5) 0.006(4) 0.002(4) -0.004(4) C12 0.024(4) 0.020(4) 0.042(4) 0.001(3) 0.002(4) -0.001(3) C13 0.017(4) 0.023(4) 0.041(5) 0.005(3) -0.002(4) 0.001(4) C14 0.042(5) 0.027(5) 0.034(4) -0.002(4) 0.010(4) 0.004(4) C15 0.040(5) 0.040(5) 0.027(4) 0.001(4) -0.004(4) -0.007(4) C16 0.034(4) 0.037(5) 0.035(4) 0.008(4) -0.006(4) -0.002(4) C17 0.024(4) 0.025(4) 0.036(4) -0.006(3) -0.001(3) 0.002(4) O1 0.022(3) 0.047(3) 0.047(3) -0.015(3) -0.008(3) 0.004(3) O2 0.048(3) 0.014(3) 0.045(3) -0.008(2) -0.002(3) -0.002(2) O3 0.062(4) 0.022(3) 0.029(3) 0.004(2) -0.006(3) -0.012(3) S1 0.0276(10) 0.0263(10) 0.0352(10) -0.0049(9) -0.0037(9) -0.0005(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C3 1.524(9) . ? C1 C2 1.537(11) . ? C1 S1 1.730(7) . ? C1 H1 1.0000 . ? C2 C4 1.494(11) . ? C2 C3 1.513(10) . ? C2 H2 1.0000 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O3 1.417(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O3 1.431(9) . ? C5 C6 1.501(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.383(11) . ? C6 C7 1.387(10) . ? C7 C8 1.387(10) . ? C7 H7 0.9500 . ? C8 C9 1.397(11) . ? C8 H8 0.9500 . ? C9 C10 1.378(11) . ? C9 H9 0.9500 . ? C10 C11 1.367(10) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C17 1.398(10) . ? C12 C13 1.399(10) . ? C12 S1 1.763(8) . ? C13 C14 1.394(10) . ? C13 H13 0.9500 . ? C14 C15 1.401(11) . ? C14 H14 0.9500 . ? C15 C16 1.400(11) . ? C15 H15 0.9500 . ? C16 C17 1.368(10) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? O1 S1 1.446(5) . ? O2 S1 1.465(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 C3 C1 C2 59.2(5) . . ? C3 C1 S1 118.2(5) . . ? C2 C1 S1 118.2(5) . . ? C3 C1 H1 116.3 . . ? C2 C1 H1 116.3 . . ? S1 C1 H1 116.3 . . ? C4 C2 C3 122.5(7) . . ? C4 C2 C1 115.7(7) . . ? C3 C2 C1 60.0(5) . . ? C4 C2 H2 115.6 . . ? C3 C2 H2 115.6 . . ? C1 C2 H2 115.6 . . ? C2 C3 C1 60.8(5) . . ? C2 C3 H3A 117.7 . . ? C1 C3 H3A 117.7 . . ? C2 C3 H3B 117.7 . . ? C1 C3 H3B 117.7 . . ? H3A C3 H3B 114.8 . . ? O3 C4 C2 108.4(6) . . ? O3 C4 H4A 110.0 . . ? C2 C4 H4A 110.0 . . ? O3 C4 H4B 110.0 . . ? C2 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? O3 C5 C6 109.6(6) . . ? O3 C5 H5A 109.8 . . ? C6 C5 H5A 109.8 . . ? O3 C5 H5B 109.8 . . ? C6 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C11 C6 C7 118.5(7) . . ? C11 C6 C5 119.9(7) . . ? C7 C6 C5 121.6(7) . . ? C8 C7 C6 120.6(7) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.2(7) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 118.4(7) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C11 C10 C9 121.3(8) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 121.0(8) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? C17 C12 C13 121.3(7) . . ? C17 C12 S1 119.5(6) . . ? C13 C12 S1 119.2(6) . . ? C14 C13 C12 118.4(7) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C15 120.4(7) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 119.8(7) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 120.3(7) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 119.7(7) . . ? C16 C17 H17 120.2 . . ? C12 C17 H17 120.2 . . ? C4 O3 C5 113.2(5) . . ? O1 S1 O2 118.1(3) . . ? O1 S1 C1 109.3(3) . . ? O2 S1 C1 108.2(3) . . ? O1 S1 C12 107.3(3) . . ? O2 S1 C12 108.2(3) . . ? C1 S1 C12 104.9(3) . . ? 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 C3 C1 C2 C4 114.3(8) . . . . ? S1 C1 C2 C4 -137.9(6) . . . . ? S1 C1 C2 C3 107.8(6) . . . . ? C4 C2 C3 C1 -103.0(8) . . . . ? S1 C1 C3 C2 -107.8(7) . . . . ? C3 C2 C4 O3 143.0(7) . . . . ? C1 C2 C4 O3 73.6(9) . . . . ? O3 C5 C6 C11 -162.1(6) . . . . ? O3 C5 C6 C7 18.7(9) . . . . ? C11 C6 C7 C8 -1.6(11) . . . . ? C5 C6 C7 C8 177.6(7) . . . . ? C6 C7 C8 C9 -0.9(12) . . . . ? C7 C8 C9 C10 2.2(12) . . . . ? C8 C9 C10 C11 -1.1(12) . . . . ? C9 C10 C11 C6 -1.5(12) . . . . ? C7 C6 C11 C10 2.8(11) . . . . ? C5 C6 C11 C10 -176.5(7) . . . . ? C17 C12 C13 C14 4.5(11) . . . . ? S1 C12 C13 C14 -179.5(6) . . . . ? C12 C13 C14 C15 -2.3(11) . . . . ? C13 C14 C15 C16 -0.2(12) . . . . ? C14 C15 C16 C17 0.7(12) . . . . ? C15 C16 C17 C12 1.4(11) . . . . ? C13 C12 C17 C16 -4.1(11) . . . . ? S1 C12 C17 C16 179.9(6) . . . . ? C2 C4 O3 C5 171.3(6) . . . . ? C6 C5 O3 C4 -171.0(6) . . . . ? C3 C1 S1 O1 26.9(6) . . . . ? C2 C1 S1 O1 -41.4(6) . . . . ? C3 C1 S1 O2 -103.0(6) . . . . ? C2 C1 S1 O2 -171.2(5) . . . . ? C3 C1 S1 C12 141.7(6) . . . . ? C2 C1 S1 C12 73.4(6) . . . . ? C17 C12 S1 O1 -164.3(6) . . . . ? C13 C12 S1 O1 19.6(7) . . . . ? C17 C12 S1 O2 -35.8(7) . . . . ? C13 C12 S1 O2 148.1(6) . . . . ? C17 C12 S1 C1 79.5(7) . . . . ? C13 C12 S1 C1 -96.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 24.40 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.571 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.094