# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Storkey, Corin' 'Davies, Michael' 'White, Jonathan M.' 'Schiesser, Carl' _publ_contact_author_name 'Schiesser, Carl' _publ_contact_author_email carlhs@unimelb.edu.au _publ_section_title ; Synthesis and Antioxidant Capacity of 5-Selenopyranose Derivatives ; # Attachment '- CC-COM-06-2011-013652_8.cif' data_jmwcs23 _database_code_depnum_ccdc_archive 'CCDC 834983' #TrackingRef '- CC-COM-06-2011-013652_8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H12 O4 S' _chemical_formula_weight 180.22 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_space_group_name_H-M 'P 21 21 21' _symmetry_cell_setting orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.53550(10) _cell_length_b 11.5250(2) _cell_length_c 11.6990(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 746.36(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0 _cell_measurement_reflns_used 7705 _cell_measurement_theta_min 3.4759 _cell_measurement_theta_max 29.0120 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6387 _exptl_crystal_size_mid 0.4061 _exptl_crystal_size_min 0.3169 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.396 _exptl_absorpt_correction_T_min 0.65385 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9451 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 29.08 _reflns_number_total 1877 _reflns_number_gt 1840 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution ? _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.1604P] 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 0.007(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_number_reflns 1877 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0198 _refine_ls_R_factor_gt 0.0192 _refine_ls_wR_factor_ref 0.0491 _refine_ls_wR_factor_gt 0.0488 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 S1 S 0.72381(5) 0.16149(2) 0.93216(2) 0.01238(8) Uani 1 1 d . . . O3 O 0.81467(16) -0.04557(7) 0.75068(7) 0.01531(19) Uani 1 1 d . . . O4 O 1.31349(16) -0.04102(7) 0.92508(9) 0.0202(2) Uani 1 1 d . . . O1 O 0.51810(16) 0.24024(8) 0.60951(7) 0.01379(18) Uani 1 1 d . . . O2 O 1.03512(15) 0.23889(7) 0.66646(7) 0.01272(18) Uani 1 1 d . . . C3 C 0.8836(2) 0.13925(9) 0.66911(9) 0.0104(2) Uani 1 1 d . . . H3 H 0.8801 0.1041 0.5929 0.013 Uiso 1 1 calc R . . C5 C 1.0044(2) 0.10080(9) 0.87532(9) 0.0114(2) Uani 1 1 d . . . H5 H 1.1243 0.1632 0.8718 0.014 Uiso 1 1 calc R . . C2 C 0.6291(2) 0.17873(10) 0.70080(9) 0.0109(2) Uani 1 1 d . . . H2 H 0.5325 0.1089 0.7148 0.013 Uiso 1 1 calc R . . C4 C 0.9771(2) 0.04975(9) 0.75500(10) 0.0107(2) Uani 1 1 d . . . H4 H 1.1361 0.0230 0.7293 0.013 Uiso 1 1 calc R . . C1 C 0.6304(2) 0.24934(10) 0.81112(9) 0.0120(2) Uani 1 1 d . . . H1A H 0.4698 0.2799 0.8251 0.014 Uiso 1 1 calc R . . H1B H 0.7399 0.3145 0.8029 0.014 Uiso 1 1 calc R . . C6 C 1.0928(2) 0.01062(11) 0.96153(10) 0.0162(2) Uani 1 1 d . . . H6A H 1.1167 0.0475 1.0352 0.019 Uiso 1 1 calc R . . H6B H 0.9710 -0.0492 0.9706 0.019 Uiso 1 1 calc R . . H3A H 0.882(3) -0.0983(17) 0.7733(15) 0.026(5) Uiso 1 1 d . . . H2A H 1.157(3) 0.2303(15) 0.6305(15) 0.026(5) Uiso 1 1 d . . . H1 H 0.578(3) 0.2982(15) 0.6027(16) 0.026(5) Uiso 1 1 d . . . H4A H 1.423(4) 0.0087(19) 0.9219(18) 0.048(6) Uiso 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 S1 0.01261(13) 0.01368(13) 0.01084(13) -0.00095(10) 0.00116(10) 0.00006(10) O3 0.0163(4) 0.0077(4) 0.0219(4) 0.0001(3) -0.0036(4) -0.0019(3) O4 0.0132(4) 0.0130(4) 0.0344(5) 0.0014(4) -0.0062(4) 0.0003(3) O1 0.0111(4) 0.0139(4) 0.0163(4) 0.0034(3) -0.0031(3) -0.0001(3) O2 0.0099(4) 0.0107(4) 0.0176(4) 0.0003(3) 0.0039(3) -0.0016(3) C3 0.0104(5) 0.0099(5) 0.0110(5) -0.0009(4) 0.0003(4) -0.0014(4) C5 0.0102(5) 0.0113(5) 0.0128(5) 0.0001(4) -0.0010(4) -0.0003(4) C2 0.0098(5) 0.0109(5) 0.0120(5) 0.0008(4) -0.0009(4) -0.0006(4) C4 0.0095(5) 0.0087(5) 0.0139(5) -0.0019(4) 0.0004(4) 0.0007(4) C1 0.0109(5) 0.0113(5) 0.0139(5) -0.0003(4) 0.0009(4) 0.0018(4) C6 0.0180(6) 0.0149(5) 0.0158(6) 0.0008(4) -0.0039(5) 0.0013(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 S1 C1 1.8158(12) . ? S1 C5 1.8286(12) . ? O3 C4 1.4204(14) . ? O4 C6 1.4242(15) . ? O1 C2 1.4215(14) . ? O2 C3 1.4224(13) . ? C3 C2 1.5263(15) . ? C3 C4 1.5301(15) . ? C5 C6 1.5287(16) . ? C5 C4 1.5330(15) . ? C2 C1 1.5258(15) . ? 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 C1 S1 C5 99.88(5) . . ? O2 C3 C2 107.99(8) . . ? O2 C3 C4 111.05(9) . . ? C2 C3 C4 110.70(9) . . ? C6 C5 C4 112.11(9) . . ? C6 C5 S1 106.98(8) . . ? C4 C5 S1 113.39(8) . . ? O1 C2 C1 111.81(9) . . ? O1 C2 C3 111.41(9) . . ? C1 C2 C3 111.10(9) . . ? O3 C4 C3 106.49(9) . . ? O3 C4 C5 113.08(9) . . ? C3 C4 C5 112.19(8) . . ? C2 C1 S1 111.32(8) . . ? O4 C6 C5 111.17(10) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 29.08 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.310 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.040