#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011649.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011649 loop_ _publ_author_name 'Hosomi, Hiroyuki' 'Ohba, Shigeru' 'Ogawa, Seiichiro' 'Takahashi, Atsushi' _publ_section_title ; (--)-epi-Inosose-2 ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e584 _journal_page_last e585 _journal_paper_doi 10.1107/S0108270100015092 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C6 H10 O6' _chemical_formula_sum 'C6 H10 O6' _chemical_formula_weight 178.14 _chemical_name_common (-)-epi-inosose _chemical_name_systematic ; (-)-2L-(2,3,4,6/5)-2,3,4,5,6-pentahydroxycyclohexanone ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 90.21(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.197(2) _cell_length_b 8.932(2) _cell_length_c 6.976(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298.0(10) _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 13.9 _cell_volume 697.7(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993) ; _computing_data_reduction ;TEXSAN (Molecular Structure Corporation, 1999) ; _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \q-2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .005 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2250 _diffrn_reflns_theta_max 30.0 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .155 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_size_max .7 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .15 _refine_diff_density_max .30 _refine_diff_density_min -.16 _refine_ls_extinction_coef .027(5) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.13 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 298 _refine_ls_number_reflns 2151 _refine_ls_R_factor_gt .024 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.0417P)^2^+0.0965P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .068 _reflns_number_gt 2086 _reflns_number_total 2151 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qa0445.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2011649 _cod_database_fobs_code 2011649 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 1.04570(10) .3579(2) .3761(2) .0324(3) Uani d . 1.00 . . O O2 .82610(10) .40610(10) .5071(2) .0242(2) Uani d . 1.00 . . O O3 .69860(10) .6413(2) .3049(2) .0294(3) Uani d . 1.00 . . O O4 .80900(10) .7696(2) -.0089(2) .0238(2) Uani d . 1.00 . . O O5 .98480(10) .5525(2) -.0615(2) .0249(2) Uani d . 1.00 . . O O6 1.18929(9) .5535(2) .1883(2) .0237(2) Uani d . 1.00 . . O O51 .68330(10) .29210(10) .0910(2) .0285(2) Uani d . 1.00 . . O O52 .46010(10) .2429(2) -.0112(2) .0324(3) Uani d . 1.00 . . O O53 .33390(10) .01070(10) .2045(2) .0243(2) Uani d . 1.00 . . O O54 .45270(10) -.07820(10) .5493(2) .0230(2) Uani d . 1.00 . . O O55 .63010(10) .14310(10) .5620(2) .0213(2) Uani d . 1.00 . . O O56 .82685(9) .1161(2) .3082(2) .0253(2) Uani d . 1.00 . . O C7 1.00740(10) .4828(2) .3542(2) .0187(2) Uani d . 1.00 . . C C8 .88410(10) .5307(2) .4220(2) .0180(2) Uani d . 1.00 . . C C9 .81300(10) .5875(2) .2481(2) .0180(2) Uani d . 1.00 . . C C10 .87810(10) .7153(2) .1488(2) .0173(2) Uani d . 1.00 . . C C11 1.00150(10) .6653(2) .0804(2) .0185(2) Uani d . 1.00 . . C C12 1.07560(10) .6045(2) .2491(2) .0182(2) Uani d . 1.00 . . C C57 .64210(10) .1728(2) .1383(2) .0186(2) Uani d . 1.00 . . C C58 .51680(10) .1235(2) .0823(2) .0203(3) Uani d . 1.00 . . C C59 .44750(10) .0722(2) .2611(2) .0170(2) Uani d . 1.00 . . C C60 .51790(10) -.0408(2) .3806(2) .0167(2) Uani d . 1.00 . . C C61 .64090(10) .0172(2) .4381(2) .0167(2) Uani d . 1.00 . . C C62 .71210(10) .0617(2) .2592(2) .0187(2) Uani d . 1.00 . . C H2 .781(3) .434(4) .581(4) .04721(10) Uiso d . 1.00 . . H H3 .663(2) .565(3) .345(4) .03637(8) Uiso d . 1.00 . . H H4 .803(3) .707(4) -.077(4) .04860(10) Uiso d . 1.00 . . H H5 1.041(2) .563(4) -.136(4) .04258(9) Uiso d . 1.00 . . H H6 1.182(2) .472(3) .160(4) .03219(8) Uiso d . 1.00 . . H H8 .891(2) .612(3) .514(3) .02305(6) Uiso d . 1.00 . . H H9 .804(2) .509(3) .162(3) .02171(6) Uiso d . 1.00 . . H H10 .883(2) .803(3) .240(3) .02047(6) Uiso d . 1.00 . . H H11 1.042(2) .753(3) .026(3) .02184(6) Uiso d . 1.00 . . H H12 1.085(2) .683(2) .342(3) .01721(6) Uiso d . 1.00 . . H H52 .402(3) .212(5) -.077(5) .07530(10) Uiso d . 1.00 . . H H53 .343(2) -.055(4) .126(4) .04038(9) Uiso d . 1.00 . . H H54 .423(2) -.161(3) .525(3) .02950(7) Uiso d . 1.00 . . H H55 .681(2) .126(4) .642(4) .04366(9) Uiso d . 1.00 . . H H56 .822(3) .208(4) .356(4) .05170(10) Uiso d . 1.00 . . H H58 .526(2) .037(3) .000(3) .02508(7) Uiso d . 1.00 . . H H59 .429(2) .157(3) .341(3) .01975(6) Uiso d . 1.00 . . H H60 .526(2) -.130(3) .319(3) .02068(6) Uiso d . 1.00 . . H H61 .682(2) -.063(3) .504(3) .02241(6) Uiso d . 1.00 . . H H62 .718(2) -.033(3) .188(3) .02101(6) Uiso d . 1.00 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0308(6) .0247(6) .0417(7) .0090(5) .0066(5) .0090(5) O2 .0270(5) .0205(5) .0252(5) .0009(4) .0082(4) .0062(4) O3 .0178(5) .0320(6) .0384(6) .0050(5) .0080(4) .0114(6) O4 .0240(5) .0256(6) .0219(5) .0035(4) -.0030(4) .0059(5) O5 .0229(5) .0322(6) .0196(4) .0004(5) .0018(4) -.0048(4) O6 .0135(4) .0280(6) .0295(5) .0001(4) -.0008(4) -.0011(5) O51 .0277(5) .0249(6) .0328(6) -.0082(5) -.0018(4) .0058(5) O52 .0313(6) .0316(7) .0344(6) -.0084(5) -.0145(5) .0160(5) O53 .0185(4) .0299(6) .0244(5) -.0059(4) -.0025(4) -.0014(5) O54 .0236(5) .0247(6) .0207(5) -.0035(4) .0058(4) .0034(4) O55 .0226(5) .0219(5) .0195(5) .0020(4) -.0021(4) -.0040(4) O56 .0134(4) .0339(6) .0287(5) -.0012(4) .0023(4) -.0007(5) C7 .0184(5) .0211(6) .0165(5) .0000(5) -.0019(4) .0011(5) C8 .0200(6) .0163(6) .0176(5) .0001(5) .0016(4) .0014(5) C9 .0160(5) .0180(6) .0201(6) .0010(5) .0007(4) .0025(5) C10 .0172(5) .0157(6) .0190(6) .0015(5) -.0002(4) .0029(4) C11 .0161(5) .0188(6) .0206(6) -.0007(5) .0009(4) .0022(5) C12 .0145(5) .0197(6) .0204(6) -.0003(5) -.0008(4) -.0012(5) C57 .0190(6) .0222(7) .0147(5) -.0012(5) .0024(4) -.0008(5) C58 .0228(6) .0218(7) .0163(5) -.0053(5) -.0023(4) .0035(5) C59 .0163(5) .0175(6) .0172(5) -.0025(5) -.0010(4) .0004(5) C60 .0185(5) .0162(6) .0153(5) -.0009(5) .0035(4) .0003(5) C61 .0161(5) .0170(6) .0171(5) .0026(5) .0011(4) .0006(5) C62 .0153(5) .0229(6) .0181(5) .0004(5) .0035(4) -.0007(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .003 .002 ;International Tables for Crystallography (1992, Vol. C) ; H H .000 .000 ;International Tables for Crystallography (1992, Vol. C) ; O O .011 .006 ;International Tables for Crystallography (1992, Vol. C) ; loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C8 O2 H2 1_555 1_555 1_555 109(2) no C9 O3 H3 1_555 1_555 1_555 104.0(10) no C10 O4 H4 1_555 1_555 1_555 106(2) no C11 O5 H5 1_555 1_555 1_555 105(2) no C12 O6 H6 1_555 1_555 1_555 107.0(10) no C58 O52 H52 1_555 1_555 1_555 110(3) no C59 O53 H53 1_555 1_555 1_555 110.0(10) no C60 O54 H54 1_555 1_555 1_555 104.0(10) no C61 O55 H55 1_555 1_555 1_555 102(2) no C62 O56 H56 1_555 1_555 1_555 110.0(10) no O1 C7 C8 1_555 1_555 1_555 122.90(10) no O1 C7 C12 1_555 1_555 1_555 123.00(10) no C8 C7 C12 1_555 1_555 1_555 114.00(10) no O2 C8 C7 1_555 1_555 1_555 109.10(10) no O2 C8 C9 1_555 1_555 1_555 110.70(10) no O2 C8 H8 1_555 1_555 1_555 110.0(10) no C7 C8 C9 1_555 1_555 1_555 108.40(10) no C7 C8 H8 1_555 1_555 1_555 109.0(10) no C9 C8 H8 1_555 1_555 1_555 108.0(10) no O3 C9 C8 1_555 1_555 1_555 110.80(10) no O3 C9 C10 1_555 1_555 1_555 107.80(10) no O3 C9 H9 1_555 1_555 1_555 109.0(10) no C8 C9 C10 1_555 1_555 1_555 111.10(10) no C8 C9 H9 1_555 1_555 1_555 108.0(10) no C10 C9 H9 1_555 1_555 1_555 108.0(10) no O4 C10 C9 1_555 1_555 1_555 110.30(10) no O4 C10 C11 1_555 1_555 1_555 110.30(10) no O4 C10 H10 1_555 1_555 1_555 104.0(10) no C9 C10 C11 1_555 1_555 1_555 111.00(10) no C9 C10 H10 1_555 1_555 1_555 108.0(10) no C11 C10 H10 1_555 1_555 1_555 111.0(10) no O5 C11 C10 1_555 1_555 1_555 107.90(10) no O5 C11 C12 1_555 1_555 1_555 110.60(10) no O5 C11 H11 1_555 1_555 1_555 110.0(10) no C10 C11 C12 1_555 1_555 1_555 110.50(10) no C10 C11 H11 1_555 1_555 1_555 107.0(10) no C12 C11 H11 1_555 1_555 1_555 109.0(10) no O6 C12 C7 1_555 1_555 1_555 111.60(10) no O6 C12 C11 1_555 1_555 1_555 111.60(10) no O6 C12 H12 1_555 1_555 1_555 109.0(10) no C7 C12 C11 1_555 1_555 1_555 110.60(10) no C7 C12 H12 1_555 1_555 1_555 104.0(10) no C11 C12 H12 1_555 1_555 1_555 108.0(10) no O51 C57 C58 1_555 1_555 1_555 122.60(10) no O51 C57 C62 1_555 1_555 1_555 122.10(10) no C58 C57 C62 1_555 1_555 1_555 115.30(10) no O52 C58 C57 1_555 1_555 1_555 108.40(10) no O52 C58 C59 1_555 1_555 1_555 112.00(10) no O52 C58 H58 1_555 1_555 1_555 112.0(10) no C57 C58 C59 1_555 1_555 1_555 110.20(10) no C57 C58 H58 1_555 1_555 1_555 106.0(10) no C59 C58 H58 1_555 1_555 1_555 107.0(10) no O53 C59 C58 1_555 1_555 1_555 109.80(10) no O53 C59 C60 1_555 1_555 1_555 110.60(10) no O53 C59 H59 1_555 1_555 1_555 105.0(10) no C58 C59 C60 1_555 1_555 1_555 112.20(10) no C58 C59 H59 1_555 1_555 1_555 110.0(10) no C60 C59 H59 1_555 1_555 1_555 108.0(10) no O54 C60 C59 1_555 1_555 1_555 109.90(10) no O54 C60 C61 1_555 1_555 1_555 109.10(10) no O54 C60 H60 1_555 1_555 1_555 103.0(10) no C59 C60 C61 1_555 1_555 1_555 112.60(10) no C59 C60 H60 1_555 1_555 1_555 111.0(10) no C61 C60 H60 1_555 1_555 1_555 109.0(10) no O55 C61 C60 1_555 1_555 1_555 110.50(10) no O55 C61 C62 1_555 1_555 1_555 109.50(10) no O55 C61 H61 1_555 1_555 1_555 109.0(10) no C60 C61 C62 1_555 1_555 1_555 110.20(10) no C60 C61 H61 1_555 1_555 1_555 107.0(10) no C62 C61 H61 1_555 1_555 1_555 109.0(10) no O56 C62 C57 1_555 1_555 1_555 112.10(10) no O56 C62 C61 1_555 1_555 1_555 111.50(10) no O56 C62 H62 1_555 1_555 1_555 110.0(10) no C57 C62 C61 1_555 1_555 1_555 110.60(10) no C57 C62 H62 1_555 1_555 1_555 108.0(10) no C61 C62 H62 1_555 1_555 1_555 103.0(10) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 . . 1.205(2) yes O2 C8 . . 1.419(2) yes O2 H2 . . .76(3) no O3 C9 . . 1.425(2) yes O3 H3 . . .84(3) no O4 C10 . . 1.428(2) yes O4 H4 . . .73(3) no O5 C11 . . 1.424(2) yes O5 H5 . . .82(3) no O6 C12 . . 1.418(2) yes O6 H6 . . .76(3) no O51 C57 . . 1.207(2) yes O52 C58 . . 1.401(2) yes O52 H52 . . .85(4) no O53 C59 . . 1.440(2) yes O53 H53 . . .81(3) no O54 C60 . . 1.427(2) yes O54 H54 . . .83(3) no O55 C61 . . 1.424(2) yes O55 H55 . . .81(3) no O56 C62 . . 1.414(2) yes O56 H56 . . .89(4) no C7 C8 . . 1.522(2) no C7 C12 . . 1.518(2) no C8 C9 . . 1.535(2) no C8 H8 . . .97(2) no C9 C10 . . 1.523(2) no C9 H9 . . .93(2) no C10 C11 . . 1.530(2) no C10 H10 . . 1.01(2) no C11 C12 . . 1.536(2) no C11 H11 . . .98(2) no C12 H12 . . .96(2) no C57 C58 . . 1.521(2) no C57 C62 . . 1.519(2) no C58 C59 . . 1.541(2) no C58 H58 . . .97(3) no C59 C60 . . 1.526(2) no C59 H59 . . .96(2) no C60 C61 . . 1.523(2) no C60 H60 . . .91(2) no C61 C62 . . 1.535(2) no C61 H61 . . .96(2) no C62 H62 . . .98(2) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2 H2 O53 2_656 .76(3) 2.09(3) 2.856(2) 177(3) O3 H3 O54 2_656 .84(3) 1.96(3) 2.786(2) 166(3) O4 H4 O53 2_655 .73(3) 2.49(3) 3.123(2) 145(3) O5 H5 O56 2_755 .82(3) 1.97(3) 2.785(2) 173(4) O6 H6 O4 2_745 .76(3) 2.10(3) 2.828(2) 163(3) O52 H52 O3 2_645 .85(4) 2.04(4) 2.856(2) 161(3) O53 H53 O51 2_645 .81(3) 2.06(3) 2.845(2) 164(3) O54 H54 O55 2_646 .83(3) 1.94(3) 2.767(2) 172(2) O55 H55 O6 2_746 .81(3) 1.98(3) 2.782(2) 170(3) O56 H56 O2 . .89(4) 2.06(4) 2.938(2) 170(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8053207 2 PubChem 139058060