Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Benjamin G. Davis' 'Antony J. Fairbanks' 'David P. Gamblin' 'Philippe Garnier' 'Neil J. Oldham' ; S.J.Ward ; _publ_contact_author_name 'Dr Benjamin G. Davis' _publ_contact_author_address ; Department of Chemistry University of Oxford Dyson Perrins Laboratory South Parks Road Oxford OX1 3QY UNITED KINGDOM ; _publ_contact_author_email BEN.DAVIS@CHEM.OX.AC.UK _publ_section_title ; Glycosyl phenylthiosulfonates (Glyco-PTS): Novel Reagents for Glycoprotein Synthesis ; data_CRYSTALS_cif _database_code_CSD 213234 #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _chemical_absolute_configuration rmad #============================================================= _cell_length_a 10.7470(3) _cell_angle_alpha 90 _cell_length_b 8.3113(2) _cell_angle_beta 100.4321(12) _cell_length_c 13.5613(4) _cell_angle_gamma 90 _cell_volume 1191.3 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C20 H24 O11 S2 ' _chemical_formula_moiety ' C20 H24 O11 S2 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 504.52 _cell_measurement_reflns_used 10203 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 200 _cell_formula_units_Z 2 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.28 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 528.648 _exptl_absorpt_coefficient_mu 0.280 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.92 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 10203 _reflns_number_total 4755 #4759 unique reflections including systematic absences _diffrn_reflns_av_R_equivalents 0.024 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_gt 3881 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -9 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _refine_diff_density_min -0.40 _refine_diff_density_max 0.36 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 3881 _refine_ls_number_parameters 298 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.0465 _refine_ls_goodness_of_fit_ref 1.0631 _refine_ls_shift/su_max 0.000224 _refine_ls_abs_structure_Flack -0.01(8) _refine_ls_abs_structure_details 'Flack, 1862 Friedel-pairs' _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 4 parameters (Carruthers & Watkin , 1979) 2.88 -.203 1.44 0.175 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type O1 0.22336(17) 0.1065(2) 0.21698(13) 0.0467 1.0000 Uani C1 0.3348(2) 0.2003(4) 0.2232(2) 0.0442 1.0000 Uani C2 0.3256(2) 0.3445(3) 0.2911(2) 0.0402 1.0000 Uani C3 0.3080(2) 0.2892(3) 0.39476(19) 0.0395 1.0000 Uani C4 0.1986(2) 0.1711(3) 0.3861(2) 0.0424 1.0000 Uani C5 0.2133(2) 0.0366(4) 0.3121(2) 0.0450 1.0000 Uani S1 0.34526(8) 0.27211(12) 0.09878(6) 0.0558 1.0000 Uani S2 0.39905(7) 0.05903(12) 0.03654(6) 0.0543 1.0000 Uani O2 0.4797(2) -0.0269(3) 0.11365(19) 0.0710 1.0000 Uani O3 0.4435(3) 0.1116(4) -0.0514(2) 0.0835 1.0000 Uani C6 0.2598(3) -0.0526(4) -0.0006(2) 0.0493 1.0000 Uani C7 0.2400(4) -0.1853(5) 0.0535(3) 0.0814 1.0000 Uani C8 0.1295(5) -0.2721(7) 0.0255(4) 0.1145 1.0000 Uani C9 0.0427(4) -0.2275(9) -0.0554(4) 0.1037 1.0000 Uani C10 0.0640(4) -0.0956(7) -0.1100(4) 0.0911 1.0000 Uani C11 0.1740(3) -0.0031(5) -0.0837(2) 0.0679 1.0000 Uani O4 0.44155(15) 0.4336(2) 0.29907(14) 0.0435 1.0000 Uani C12 0.4338(3) 0.5963(3) 0.28954(19) 0.0437 1.0000 Uani O5 0.3351(2) 0.6669(3) 0.2788(2) 0.0657 1.0000 Uani C13 0.5613(3) 0.6698(4) 0.2952(2) 0.0595 1.0000 Uani O6 0.27377(15) 0.4272(2) 0.44855(14) 0.0436 1.0000 Uani C14 0.3662(2) 0.5080(4) 0.5112(2) 0.0449 1.0000 Uani O7 0.47348(18) 0.4613(3) 0.53123(17) 0.0585 1.0000 Uani C15 0.3169(3) 0.6575(4) 0.5477(3) 0.0616 1.0000 Uani O8 0.19953(17) 0.0973(3) 0.48230(14) 0.0476 1.0000 Uani C16 0.0938(3) 0.1131(5) 0.5247(3) 0.0737 1.0000 Uani O9 0.0049(3) 0.1897(6) 0.4872(4) 0.1434 1.0000 Uani C17 0.1038(4) 0.0176(5) 0.6183(3) 0.0805 1.0000 Uani C18 0.1025(3) -0.0780(4) 0.2928(2) 0.0534 1.0000 Uani O10 -0.00972(18) 0.0183(3) 0.2596(2) 0.0743 1.0000 Uani C19 -0.1157(3) -0.0546(5) 0.2315(3) 0.0686 1.0000 Uani O11 -0.1203(4) -0.1949(5) 0.2331(5) 0.1885 1.0000 Uani C20 -0.2249(3) 0.0525(7) 0.2000(3) 0.0911 1.0000 Uani H11 0.4111 0.1345 0.2508 0.0519 1.0000 Uiso H21 0.2512 0.4127 0.2623 0.0467 1.0000 Uiso H31 0.3881 0.2375 0.4295 0.0464 1.0000 Uiso H41 0.1181 0.2312 0.3625 0.0498 1.0000 Uiso H51 0.2904 -0.0251 0.3431 0.0528 1.0000 Uiso H71 0.3044 -0.2193 0.1126 0.0953 1.0000 Uiso H81 0.1134 -0.3688 0.0652 0.1378 1.0000 Uiso H91 -0.0368 -0.2913 -0.0750 0.1266 1.0000 Uiso H101 -0.0002 -0.0644 -0.1700 0.1051 1.0000 Uiso H111 0.1897 0.0941 -0.1231 0.0793 1.0000 Uiso H131 0.5526 0.7892 0.2880 0.0713 1.0000 Uiso H132 0.6150 0.6435 0.3614 0.0713 1.0000 Uiso H133 0.6018 0.6260 0.2400 0.0713 1.0000 Uiso H151 0.3865 0.7143 0.5935 0.0738 1.0000 Uiso H152 0.2474 0.6311 0.5850 0.0738 1.0000 Uiso H153 0.2834 0.7285 0.4895 0.0738 1.0000 Uiso H171 0.0251 0.0321 0.6470 0.1002 1.0000 Uiso H172 0.1786 0.0552 0.6679 0.1002 1.0000 Uiso H173 0.1144 -0.0987 0.6030 0.1002 1.0000 Uiso H181 0.0950 -0.1369 0.3558 0.0629 1.0000 Uiso H182 0.1140 -0.1572 0.2397 0.0629 1.0000 Uiso H201 -0.3031 -0.0137 0.1795 0.1065 1.0000 Uiso H202 -0.2358 0.1241 0.2571 0.1065 1.0000 Uiso H203 -0.2101 0.1197 0.1421 0.1065 1.0000 Uiso 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 0.0440(9) 0.0447(11) 0.046(1) 0.0066(9) -0.0050(8) -0.0142(8) C1 0.0377(12) 0.0458(16) 0.0462(14) 0.0103(12) 0.000(1) -0.0088(11) C2 0.0292(11) 0.0402(15) 0.0474(14) 0.0063(11) -0.003(1) -0.007(1) C3 0.0282(11) 0.0405(14) 0.0473(13) 0.0058(12) 0.0004(9) -0.002(1) C4 0.0304(11) 0.0418(15) 0.0524(14) 0.0136(12) 0.000(1) -0.003(1) C5 0.0378(12) 0.0415(16) 0.0528(14) 0.0144(12) 0.000(1) -0.0073(11) S1 0.0702(5) 0.0478(4) 0.0481(4) 0.0082(3) 0.0071(3) -0.0134(4) S2 0.0462(3) 0.0610(5) 0.0574(4) -0.0009(4) 0.0137(3) -0.0120(3) O2 0.0482(11) 0.0721(17) 0.0843(16) -0.0057(13) -0.0100(11) 0.0039(11) O3 0.0901(18) 0.091(2) 0.0816(17) -0.0023(15) 0.0470(14) -0.0252(16) C6 0.0455(14) 0.0590(19) 0.0426(13) -0.0083(13) 0.0059(11) -0.0061(13) C7 0.095(3) 0.086(3) 0.0580(19) 0.0037(19) -0.0022(18) -0.048(2) C8 0.121(4) 0.145(5) 0.078(3) -0.025(3) 0.021(3) -0.091(4) C9 0.065(2) 0.151(5) 0.101(3) -0.063(4) 0.030(2) -0.046(3) C10 0.0507(19) 0.123(4) 0.089(3) -0.056(3) -0.0154(19) 0.019(2) C11 0.0655(19) 0.075(3) 0.0572(18) -0.0176(17) -0.0037(15) 0.0179(17) O4 0.0306(8) 0.0440(11) 0.053(1) 0.0066(9) -0.0003(7) -0.0099(7) C12 0.0548(15) 0.0383(16) 0.0381(12) 0.0029(11) 0.0084(11) -0.0103(12) O5 0.0635(14) 0.0457(13) 0.0880(17) 0.0102(12) 0.0141(12) 0.0000(11) C13 0.0647(19) 0.063(2) 0.0503(16) 0.0006(15) 0.0099(14) -0.0293(16) O6 0.0311(8) 0.0460(11) 0.052(1) -0.0011(9) 0.0033(7) -0.0034(8) C14 0.0337(12) 0.0537(17) 0.0453(13) 0.0031(12) 0.002(1) -0.0113(11) O7 0.038(1) 0.0632(15) 0.0672(13) -0.0030(11) -0.0089(9) -0.003(1) C15 0.0500(16) 0.064(2) 0.070(2) -0.0129(17) 0.0103(14) -0.0089(15) O8 0.0406(9) 0.0487(12) 0.054(1) 0.0116(9) 0.0095(8) -0.0009(8) C16 0.0509(17) 0.085(3) 0.091(3) 0.026(2) 0.0271(17) -0.0070(18) O9 0.0580(15) 0.218(5) 0.168(3) 0.109(3) 0.0563(19) 0.043(2) C17 0.097(3) 0.079(3) 0.075(2) 0.015(2) 0.039(2) -0.025(2) C18 0.0478(15) 0.0428(17) 0.0666(18) 0.0102(14) 0.0021(13) -0.0096(13) O10 0.038(1) 0.0559(15) 0.119(2) 0.0138(14) -0.0115(11) -0.019(1) C19 0.0589(19) 0.073(3) 0.068(2) 0.0110(18) -0.0029(15) -0.0366(18) O11 0.109(3) 0.083(3) 0.329(7) 0.025(4) -0.078(4) -0.051(2) C20 0.0402(15) 0.129(4) 0.097(3) 0.013(3) -0.0059(16) -0.023(2) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.419(3) yes O1 . C5 . 1.437(3) yes C1 . C2 . 1.525(4) yes C1 . S1 . 1.812(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.523(4) yes C2 . O4 . 1.437(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.520(3) yes C3 . O6 . 1.442(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.529(4) yes C4 . O8 . 1.440(3) yes C4 . H41 . 1.000 no C5 . C18 . 1.510(4) yes C5 . H51 . 1.000 no S1 . S2 . 2.0880(12) yes S2 . O2 . 1.423(3) yes S2 . O3 . 1.431(3) yes S2 . C6 . 1.755(3) yes C6 . C7 . 1.362(5) yes C6 . C11 . 1.383(4) yes C7 . C8 . 1.383(5) yes C7 . H71 . 1.000 no C8 . C9 . 1.356(8) yes C8 . H81 . 1.000 no C9 . C10 . 1.366(8) yes C9 . H91 . 1.000 no C10 . C11 . 1.401(6) yes C10 . H101 . 1.000 no C11 . H111 . 1.000 no O4 . C12 . 1.359(4) yes C12 . O5 . 1.197(4) yes C12 . C13 . 1.489(4) yes C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no O6 . C14 . 1.362(3) yes C14 . O7 . 1.200(3) yes C14 . C15 . 1.471(5) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C15 . H153 . 1.000 no O8 . C16 . 1.370(4) yes C16 . O9 . 1.183(5) yes C16 . C17 . 1.484(5) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . O10 . 1.450(4) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no O10 . C19 . 1.285(4) yes C19 . O11 . 1.168(5) yes C19 . C20 . 1.473(6) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C5 . 111.65(19) yes O1 . C1 . C2 . 108.7(2) yes O1 . C1 . S1 . 108.62(17) yes C2 . C1 . S1 . 108.97(19) yes O1 . C1 . H11 . 110.3 no C2 . C1 . H11 . 110.0 no S1 . C1 . H11 . 110.1 no C1 . C2 . C3 . 110.6(2) yes C1 . C2 . O4 . 107.5(2) yes C3 . C2 . O4 . 109.71(19) yes C1 . C2 . H21 . 110.1 no C3 . C2 . H21 . 107.9 no O4 . C2 . H21 . 111.0 no C2 . C3 . C4 . 110.3(2) yes C2 . C3 . O6 . 108.2(2) yes C4 . C3 . O6 . 106.8(2) yes C2 . C3 . H31 . 108.9 no C4 . C3 . H31 . 110.3 no O6 . C3 . H31 . 112.3 no C3 . C4 . C5 . 110.6(2) yes C3 . C4 . O8 . 109.1(2) yes C5 . C4 . O8 . 107.4(2) yes C3 . C4 . H41 . 108.3 no C5 . C4 . H41 . 110.0 no O8 . C4 . H41 . 111.5 no O1 . C5 . C4 . 109.1(2) yes O1 . C5 . C18 . 106.6(2) yes C4 . C5 . C18 . 113.8(2) yes O1 . C5 . H51 . 113.2 no C4 . C5 . H51 . 105.9 no C18 . C5 . H51 . 108.5 no C1 . S1 . S2 . 99.53(11) yes S1 . S2 . O2 . 107.75(12) yes S1 . S2 . O3 . 103.69(14) yes O2 . S2 . O3 . 120.98(17) yes S1 . S2 . C6 . 106.29(11) yes O2 . S2 . C6 . 108.63(15) yes O3 . S2 . C6 . 108.55(16) yes S2 . C6 . C7 . 118.8(2) yes S2 . C6 . C11 . 119.0(3) yes C7 . C6 . C11 . 122.3(3) yes C6 . C7 . C8 . 119.0(4) yes C6 . C7 . H71 . 120.5 no C8 . C7 . H71 . 120.5 no C7 . C8 . C9 . 120.7(5) yes C7 . C8 . H81 . 119.7 no C9 . C8 . H81 . 119.7 no C8 . C9 . C10 . 120.0(4) yes C8 . C9 . H91 . 120.0 no C10 . C9 . H91 . 120.0 no C9 . C10 . C11 . 121.2(4) yes C9 . C10 . H101 . 119.4 no C11 . C10 . H101 . 119.4 no C6 . C11 . C10 . 116.9(4) yes C6 . C11 . H111 . 121.6 no C10 . C11 . H111 . 121.6 no C2 . O4 . C12 . 117.9(2) yes O4 . C12 . O5 . 122.5(3) yes O4 . C12 . C13 . 111.3(3) yes O5 . C12 . C13 . 126.2(3) yes C12 . C13 . H131 . 109.5 no C12 . C13 . H132 . 109.5 no H131 . C13 . H132 . 109.5 no C12 . C13 . H133 . 109.5 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C3 . O6 . C14 . 118.93(19) yes O6 . C14 . O7 . 123.0(3) yes O6 . C14 . C15 . 111.1(2) yes O7 . C14 . C15 . 125.9(3) yes C14 . C15 . H151 . 109.5 no C14 . C15 . H152 . 109.5 no H151 . C15 . H152 . 109.5 no C14 . C15 . H153 . 109.5 no H151 . C15 . H153 . 109.5 no H152 . C15 . H153 . 109.5 no C4 . O8 . C16 . 118.0(2) yes O8 . C16 . O9 . 122.5(3) yes O8 . C16 . C17 . 111.7(3) yes O9 . C16 . C17 . 125.7(3) yes C16 . C17 . H171 . 109.5 no C16 . C17 . H172 . 109.5 no H171 . C17 . H172 . 109.5 no C16 . C17 . H173 . 109.5 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no C5 . C18 . O10 . 106.9(2) yes C5 . C18 . H181 . 110.1 no O10 . C18 . H181 . 110.1 no C5 . C18 . H182 . 110.1 no O10 . C18 . H182 . 110.1 no H181 . C18 . H182 . 109.5 no C18 . O10 . C19 . 118.3(3) yes O10 . C19 . O11 . 120.2(4) yes O10 . C19 . C20 . 114.7(4) yes O11 . C19 . C20 . 125.0(4) yes C19 . C20 . H201 . 109.5 no C19 . C20 . H202 . 109.5 no H201 . C20 . H202 . 109.5 no C19 . C20 . H203 . 109.5 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no