# CIF-file generated for tgsc178_0m in P2(1)2(1)2(1) #============================================================================== data_global #============================================================================== # 0. AUDIT DETAILS _audit_creation_date 'Apr 13 23:46:29 2010' _audit_creation_method 'PLATON option' _audit_update_record ; ; #=============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name ; 'Prof.S.Chandrasekaran' ; _publ_contact_author_address ; Department of Organic Chemistry Indian Institute of Science Bangalore, 560 012 India ; _publ_contact_author_email 'scn@orgchem.iisc.ernet.in' _publ_contact_author_fax '(91) 80 23602423' _publ_contact_author_phone '(91) 80 22932404' _publ_requested_journal 'Private communication' _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ? #=============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and adresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_footnote _publ_author_address '?' # author name ; # author related footnote ? ; ; # Address of this author ? ; #=============================================================================== # 4. TEXT _publ_section_synopsis ; ? ; _publ_section_abstract ; ? ; # Insert blank lines between paragraphs _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; # Insert blank lines between references _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Beurskens, P.T., Beurskens, G., de Gelder, R., Garc\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF99 Program System, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Duisenberg, A.J.M. (1992). J. Appl. Cryst. 25, 92-96. Duisenberg, A.J.M., Kroon-Batenburg, L.M.J. & Schreurs, A.M.M. (2003). J. Appl. Cryst. 36, 220-229. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Flack, H.D. (1983). Acta Cryst. A39, 876-881. Hooft, R.W.W. (1998). Collect Software, Nonius B.V., Delft, The Netherlands. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C.W. Carter & R.M. Sweet, pp. 307-326. London: Academic Press. Sheldrick, G.M. (1986). SHELXS86. University of G\"ottingen, Germany. Sheldrick, G.M. (1993). SHELXL93. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXS97. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. University of G\"ottingen, Germany. Sluis, P. van der & Spek, A.L. (1990). Acta Cryst. A46, 194-201. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13. Wilson, A.J.C. (1992). Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; ? ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_tgsc178_0m #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-deoxy-5-thio-D-glucopyrano-3,6-lactone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 O4 S1' _chemical_formula_structural ? _chemical_formula_sum 'C6 H8 O4 S1' _chemical_formula_iupac ? _chemical_formula_weight 176.18 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _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 5.7460(18) _cell_length_b 11.149(4) _cell_length_c 11.329(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 725.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2312 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.0 _cell_special_details ; ? ; _exptl_crystal_description ' block' _exptl_crystal_colour ' colorless' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.406 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'APEX 2 (Bruker)' _exptl_absorpt_correction_T_min 0.9019 _exptl_absorpt_correction_T_max 0.9306 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe 'x-ray' _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 3594 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.99 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.957 _diffrn_measured_fraction_theta_full 0.950 _diffrn_reflns_reduction_process ; ? ; # number of unique reflections _reflns_number_total 1623 # number of observed reflections (> n sig(I)) _reflns_number_gt 1389 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.1536P)^2^+0.0000P] 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 ' none' _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(2) _chemical_absolute_configuration syn _refine_ls_number_reflns 1623 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.2232 _refine_ls_wR_factor_gt 0.1907 _refine_ls_goodness_of_fit_ref 1.221 _refine_ls_restrained_S_all 1.221 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.553 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.131 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.9983(2) 0.72487(9) 0.86608(8) 0.0366(4) Uani 1 1 d . . . C1 C 0.9818(9) 0.8779(3) 0.8086(3) 0.0326(9) Uani 1 1 d . . . H1 H 1.1203 0.9251 0.8284 0.039 Uiso 1 1 calc R . . C2 C 0.7571(9) 0.9369(3) 0.8530(4) 0.0362(10) Uani 1 1 d . . . O1 O 0.5812(7) 0.9156(3) 0.7747(3) 0.0410(8) Uani 1 1 d . . . C3 C 0.9302(8) 0.8789(3) 0.6757(4) 0.0319(10) Uani 1 1 d . . . H3 H 0.9410 0.9621 0.6483 0.038 Uiso 1 1 calc R . . C4 C 0.6723(8) 0.8435(3) 0.6760(4) 0.0310(9) Uani 1 1 d . . . H4 H 0.5976 0.8667 0.6016 0.037 Uiso 1 1 calc R . . O2 O 1.0814(7) 0.8089(3) 0.6054(3) 0.0382(8) Uani 1 1 d . . . H2 H 1.0453 0.7379 0.6110 0.057 Uiso 1 1 calc R . . C5 C 0.6257(8) 0.7087(3) 0.7040(4) 0.0292(8) Uani 1 1 d . . . H5 H 0.4591 0.6921 0.6952 0.035 Uiso 1 1 calc R . . C6 C 0.7017(9) 0.6758(3) 0.8293(4) 0.0360(10) Uani 1 1 d . . . H6A H 0.6925 0.5894 0.8386 0.043 Uiso 1 1 calc R . . H6B H 0.5940 0.7116 0.8850 0.043 Uiso 1 1 calc R . . O3 O 0.7537(7) 0.6369(2) 0.6214(3) 0.0380(8) Uani 1 1 d . . . H3A H 0.6775 0.6289 0.5607 0.057 Uiso 1 1 calc R . . O4 O 0.7268(9) 0.9947(3) 0.9411(4) 0.0553(11) 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 S1 0.0510(8) 0.0357(5) 0.0232(5) 0.0019(3) -0.0082(6) 0.0064(4) C1 0.043(2) 0.0290(14) 0.0252(17) -0.0058(14) -0.007(2) -0.0068(16) C2 0.051(3) 0.0285(14) 0.029(2) -0.0043(15) -0.003(2) 0.0019(17) O1 0.054(2) 0.0322(12) 0.0370(16) -0.0081(13) 0.0026(15) 0.0138(13) C3 0.049(3) 0.0256(14) 0.0210(18) 0.0013(13) 0.0002(18) -0.0037(15) C4 0.047(3) 0.0239(14) 0.0222(18) -0.0014(13) -0.0019(18) 0.0078(13) O2 0.047(2) 0.0416(13) 0.0256(14) -0.0023(13) 0.0081(14) -0.0045(14) C5 0.032(2) 0.0279(14) 0.0273(19) -0.0022(14) 0.0042(17) 0.0014(14) C6 0.051(3) 0.0291(15) 0.028(2) 0.0034(15) 0.007(2) -0.0030(16) O3 0.058(2) 0.0306(11) 0.0256(14) -0.0094(11) -0.0057(16) 0.0047(14) O4 0.071(3) 0.0540(16) 0.041(2) -0.0240(17) 0.008(2) 0.0068(19) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 1.828(4) . ? S1 C6 1.838(5) . ? C1 C2 1.535(7) . ? C1 C3 1.535(5) . ? C1 H1 0.9800 . ? C2 O4 1.200(6) . ? C2 O1 1.366(6) . ? O1 C4 1.473(5) . ? C3 O2 1.414(5) . ? C3 C4 1.533(7) . ? C3 H3 0.9800 . ? C4 C5 1.560(5) . ? C4 H4 0.9800 . ? O2 H2 0.8200 . ? C5 O3 1.434(5) . ? C5 C6 1.530(6) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O3 H3A 0.8200 . ? 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 C6 98.6(2) . . ? C2 C1 C3 99.0(4) . . ? C2 C1 S1 109.1(3) . . ? C3 C1 S1 111.5(2) . . ? C2 C1 H1 112.2 . . ? C3 C1 H1 112.2 . . ? S1 C1 H1 112.2 . . ? O4 C2 O1 121.7(5) . . ? O4 C2 C1 128.7(5) . . ? O1 C2 C1 109.6(3) . . ? C2 O1 C4 109.0(3) . . ? O2 C3 C4 116.9(3) . . ? O2 C3 C1 115.5(4) . . ? C4 C3 C1 100.6(3) . . ? O2 C3 H3 107.8 . . ? C4 C3 H3 107.8 . . ? C1 C3 H3 107.8 . . ? O1 C4 C3 101.8(3) . . ? O1 C4 C5 108.1(3) . . ? C3 C4 C5 114.4(3) . . ? O1 C4 H4 110.7 . . ? C3 C4 H4 110.7 . . ? C5 C4 H4 110.7 . . ? C3 O2 H2 109.5 . . ? O3 C5 C6 109.0(3) . . ? O3 C5 C4 108.5(3) . . ? C6 C5 C4 111.8(3) . . ? O3 C5 H5 109.2 . . ? C6 C5 H5 109.2 . . ? C4 C5 H5 109.2 . . ? C5 C6 S1 113.8(3) . . ? C5 C6 H6A 108.8 . . ? S1 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? S1 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C5 O3 H3A 109.5 . . ? 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 C6 S1 C1 C2 47.8(3) . . . . ? C6 S1 C1 C3 -60.4(4) . . . . ? C3 C1 C2 O4 -152.8(5) . . . . ? S1 C1 C2 O4 90.6(5) . . . . ? C3 C1 C2 O1 26.6(4) . . . . ? S1 C1 C2 O1 -89.9(3) . . . . ? O4 C2 O1 C4 179.5(4) . . . . ? C1 C2 O1 C4 0.0(4) . . . . ? C2 C1 C3 O2 -167.9(3) . . . . ? S1 C1 C3 O2 -53.2(5) . . . . ? C2 C1 C3 C4 -41.0(3) . . . . ? S1 C1 C3 C4 73.7(4) . . . . ? C2 O1 C4 C3 -27.0(4) . . . . ? C2 O1 C4 C5 93.9(4) . . . . ? O2 C3 C4 O1 168.3(3) . . . . ? C1 C3 C4 O1 42.5(3) . . . . ? O2 C3 C4 C5 52.0(5) . . . . ? C1 C3 C4 C5 -73.8(4) . . . . ? O1 C4 C5 O3 -168.5(3) . . . . ? C3 C4 C5 O3 -55.9(5) . . . . ? O1 C4 C5 C6 -48.3(5) . . . . ? C3 C4 C5 C6 64.3(5) . . . . ? O3 C5 C6 S1 70.2(4) . . . . ? C4 C5 C6 S1 -49.7(4) . . . . ? C1 S1 C6 C5 46.0(3) . . . . ? #===END