#------------------------------------------------------------------------------ #$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/18/2011802.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_2011802 loop_ _publ_author_name 'Foces-Foces, C.' _publ_section_title ; Three 1,6-anhydro-\b-D-glycopyranose derivatives ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 298 _journal_page_last 301 _journal_paper_doi 10.1107/S0108270100019065 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C13 H14 O5' _chemical_formula_sum 'C13 H14 O5' _chemical_formula_weight 250.25 _chemical_melting_point 470.5(5) _chemical_name_systematic 1,6-anhydro-2,3-O-(S)-benzylidene-\b-D-mannopyranose _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 96.432(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 13.0265(7) _cell_length_b 7.0672(3) _cell_length_c 6.3376(2) _cell_measurement_reflns_used 71 _cell_measurement_temperature 293 _cell_measurement_theta_max 45 _cell_measurement_theta_min 2 _cell_volume 579.77(4) _computing_cell_refinement 'LSUCRE (Appleman, 1984)' _computing_data_collection 'Philips PW1100 software (Hornstra & Vossers, 1973)' _computing_data_reduction 'Xtal3.6 (Hall et al., 1999)' _computing_molecular_graphics Xtal3.6 _computing_publication_material 'BONDLA and CIFIO in Xtal3.6' _computing_structure_refinement 'CRYLSQ in Xtal3.6' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 293 _diffrn_measurement_device_type 'Philips PW1100 four-circle' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .016 _diffrn_reflns_av_sigmaI/netI .016 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2488 _diffrn_reflns_reduction_process 'perpendicular monochr Lp' _diffrn_reflns_theta_max 67.49 _diffrn_reflns_theta_min 3.41 _diffrn_standards_decay_% none _diffrn_standards_interval_time 90 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .930 _exptl_absorpt_correction_T_max .854 _exptl_absorpt_correction_T_min .776 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_meas ? _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 264 _exptl_crystal_size_max .43 _exptl_crystal_size_mid .33 _exptl_crystal_size_min .17 _refine_diff_density_max .18 _refine_diff_density_min -.13 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.001 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 167 _refine_ls_number_reflns 1148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .029 _refine_ls_R_factor_gt .029 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = k/[(a+b Fo)^2^(c+d(sin\q)/\l)]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .032 _refine_ls_wR_factor_ref .032 _reflns_number_gt 1148 _reflns_number_total 1148 _reflns_threshold_expression I>0 _cod_data_source_file gd1120.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '470-471' was changed to '470.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '470-471' was changed to '470.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_Hall 'P 2y1' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2011802 _cod_database_fobs_code 2011802 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_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 .28160(11) .45000 .4108(2) .0333(7) Uani ? ? 1.0 ? ? O2 .35528(11) .6537(3) .7763(2) .0290(6) Uani ? ? 1.0 ? ? O3 .25646(10) .4150(3) .8805(2) .0293(6) Uani ? ? 1.0 ? ? O4 .42676(13) .0255(3) .8411(3) .0414(8) Uani ? ? 1.0 ? ? O5 .42114(11) .2565(3) .4544(2) .0347(7) Uani ? ? 1.0 ? ? C1 .38799(15) .4435(4) .4896(3) .0287(9) Uani ? ? 1.0 ? ? C2 .40562(14) .4809(4) .7277(3) .0257(8) Uani ? ? 1.0 ? ? C3 .35514(15) .3316(4) .8569(3) .0271(8) Uani ? ? 1.0 ? ? C4 .34065(15) .1360(4) .7550(3) .0301(9) Uani ? ? 1.0 ? ? C5 .33566(16) .1467(4) .5134(3) .0344(9) Uani ? ? 1.0 ? ? C6 .24399(17) .2594(5) .4120(4) .0398(11) Uani ? ? 1.0 ? ? C7 .27979(15) .6075(4) .9176(3) .0272(9) Uani ? ? 1.0 ? ? C8 .18594(15) .7290(4) .8734(3) .0283(9) Uani ? ? 1.0 ? ? C9 .15024(18) .8340(4) 1.0342(3) .0376(10) Uani ? ? 1.0 ? ? C10 .0633(2) .9475(5) .9919(4) .0491(13) Uani ? ? 1.0 ? ? C11 .0124(2) .9556(5) .7894(4) .0498(13) Uani ? ? 1.0 ? ? C12 .0479(2) .8523(5) .6276(4) .0466(12) Uani ? ? 1.0 ? ? C13 .13419(17) .7393(5) .6687(3) .0380(10) Uani ? ? 1.0 ? ? H41 .409(3) -.102(7) .802(6) .044(10) Uiso ? ? 1.0 ? ? H1 .43031 .53923 .40958 .04300 Uiso ? ? 1.0 ? ? H2 .48478 .48122 .77457 .03100 Uiso ? ? 1.0 ? ? H3 .40065 .31617 1.00138 .02900 Uiso ? ? 1.0 ? ? H4 .27254 .07696 .79551 .03200 Uiso ? ? 1.0 ? ? H5 .33933 .01083 .45219 .03700 Uiso ? ? 1.0 ? ? H6a .22163 .21199 .25868 .04200 Uiso ? ? 1.0 ? ? H6b .18209 .24890 .50175 .04200 Uiso ? ? 1.0 ? ? H7 .31007 .62870 1.07459 .03000 Uiso ? ? 1.0 ? ? H9 .18870 .82888 1.18678 .04100 Uiso ? ? 1.0 ? ? H10 .03632 1.02635 1.11253 .05300 Uiso ? ? 1.0 ? ? H11 -.05259 1.04032 .75833 .05200 Uiso ? ? 1.0 ? ? H12 .00945 .85921 .47472 .04900 Uiso ? ? 1.0 ? ? H13 .16092 .66127 .54725 .04100 Uiso ? ? 1.0 ? ? 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 .0325(7) .0404(8) .0255(6) .0027(6) -.0035(5) .0015(6) O2 .0302(7) .0245(7) .0329(7) -.0022(6) .0068(5) -.0001(6) O3 .0324(7) .0263(7) .0307(6) -.0012(6) .0104(5) .0027(6) O4 .0419(8) .0281(8) .0506(9) .0050(7) -.0107(7) .0021(7) O5 .0326(7) .0377(8) .0349(7) .0034(7) .0093(5) -.0048(6) C1 .0289(9) .0318(10) .0258(8) .0001(9) .0052(7) .0013(8) C2 .0226(8) .0243(9) .0295(9) -.0008(7) .0006(6) -.0008(8) C3 .0294(9) .0272(10) .0243(8) -.0005(8) .0014(7) .0021(8) C4 .0281(9) .0264(10) .0352(10) -.0009(8) .0010(8) .0019(9) C5 .0325(9) .0344(11) .0353(10) -.0021(9) -.0008(8) -.0073(10) C6 .0371(11) .0441(13) .0354(11) -.0045(10) -.0086(8) -.0040(10) C7 .0353(10) .0263(10) .0207(8) -.0020(8) .0055(7) -.0007(7) C8 .0309(9) .0279(10) .0271(9) -.0018(8) .0073(7) .0009(8) C9 .0447(11) .0383(12) .0313(9) -.0016(10) .0103(8) -.0048(9) C10 .0516(13) .0473(14) .0512(13) .0104(12) .0182(10) -.0099(12) C11 .0434(12) .0480(14) .0584(14) .0132(12) .0070(10) -.0007(13) C12 .0420(11) .0564(16) .0406(11) .0105(12) .0015(9) .0006(12) C13 .0376(10) .0465(13) .0300(9) .0056(11) .0037(8) -.0029(10) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 'International tables' H 0 0 'International tables' O .047 .032 'International tables' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 2 0 0 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 O1 C6 106.78(16) ? C2 O2 C7 107.5(2) ? C7 O3 C3 103.57(17) ? H41 O4 C4 105(2) ? C1 O5 C5 101.75(17) ? H1 C1 O5 110.0 ? H1 C1 O1 110.9 ? H1 C1 C2 110.0 ? O5 C1 O1 106.10(17) ? O5 C1 C2 107.65(18) ? O1 C1 C2 112.07(16) ? H2 C2 O2 113.5 ? H2 C2 C1 108.5 ? H2 C2 C3 108.7 ? O2 C2 C1 109.74(17) ? O2 C2 C3 103.8(2) yes C1 C2 C3 112.63(19) ? H3 C3 O3 112.3 ? H3 C3 C2 107.9 ? H3 C3 C4 107.9 ? O3 C3 C2 102.5(2) yes O3 C3 C4 110.2(2) yes C2 C3 C4 115.98(17) ? H4 C4 O4 110.1 ? H4 C4 C5 109.0 ? H4 C4 C3 109.1 ? O4 C4 C5 110.8(2) yes O4 C4 C3 106.2(2) yes C5 C4 C3 111.6(2) ? H5 C5 O5 109.4 ? H5 C5 C6 113.2 ? H5 C5 C4 109.3 ? O5 C5 C6 101.6(2) ? O5 C5 C4 109.87(17) ? C6 C5 C4 113.2(2) ? H6a C6 H6b 109.6 ? H6a C6 O1 111.0 ? H6a C6 C5 110.6 ? H6b C6 O1 110.9 ? H6b C6 C5 110.6 ? O1 C6 C5 104.02(18) ? H7 C7 O3 110.5 ? H7 C7 O2 110.5 ? H7 C7 C8 108.2 ? O3 C7 O2 105.35(17) ? O3 C7 C8 111.54(17) ? O2 C7 C8 110.74(18) ? C9 C8 C13 119.3(2) ? C9 C8 C7 120.37(17) ? C13 C8 C7 120.3(2) ? H9 C9 C8 120.0 ? H9 C9 C10 119.8 ? C8 C9 C10 120.1(2) ? H10 C10 C11 119.7 ? H10 C10 C9 120.3 ? C11 C10 C9 120.0(3) ? H11 C11 C10 119.8 ? H11 C11 C12 119.9 ? C10 C11 C12 120.3(3) ? H12 C12 C11 120.1 ? H12 C12 C13 120.0 ? C11 C12 C13 120.0(2) ? H13 C13 C12 120.1 ? H13 C13 C8 119.6 ? C12 C13 C8 120.3(2) ? 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 C1 . . 1.420(2) ? O1 C6 . . 1.433(3) ? O2 C2 . . 1.436(3) yes O2 C7 . . 1.440(3) ? O3 C7 . . 1.408(3) ? O3 C3 . . 1.437(3) yes O4 H41 . . .96(5) ? O4 C4 . . 1.424(3) ? O5 C1 . . 1.416(4) ? O5 C5 . . 1.441(3) ? C1 H1 . . 1.040 ? C1 C2 . . 1.524(3) ? C2 H2 . . 1.041 ? C2 C3 . . 1.528(3) ? C3 H3 . . 1.039 ? C3 C4 . . 1.529(4) ? C4 H4 . . 1.038 ? C4 C5 . . 1.527(3) ? C5 H5 . . 1.039 ? C5 C6 . . 1.517(3) ? C6 H6a . . 1.038 ? C6 H6b . . 1.040 ? C7 H7 . . 1.039 ? C7 C8 . . 1.495(3) ? C8 C9 . . 1.383(3) ? C8 C13 . . 1.395(3) ? C9 H9 . . 1.039 ? C9 C10 . . 1.389(4) ? C10 H10 . . 1.039 ? C10 C11 . . 1.379(4) ? C11 H11 . . 1.038 ? C11 C12 . . 1.379(4) ? C12 H12 . . 1.041 ? C12 C13 . . 1.380(4) ? C13 H13 . . 1.038 ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 H6a H6b 1.698 . O2 H41 1.86(5) 1_565 C4 H41 1.91(5) . O3 H7 2.022 . O5 H1 2.023 . O4 H4 2.030 . O5 H5 2.037 . O1 H1 2.038 . O1 H6b 2.049 . O1 H6a 2.050 . O2 H7 2.050 . O3 H3 2.069 . C8 H7 2.069 . O2 H2 2.082 . C2 H3 2.096 . C4 H3 2.097 . C11 H10 2.097 . C10 H11 2.098 . C12 H11 2.099 . C1 H2 2.100 . C12 H13 2.102 . C13 H12 2.103 . C11 H12 2.104 . C8 H9 2.104 . C3 H2 2.107 . C10 H9 2.108 . C5 H4 2.108 . C3 H4 2.111 . C8 H13 2.111 . C4 H5 2.111 . C9 H10 2.112 . C2 H1 2.117 . C5 H6a 2.119 . C5 H6b 2.120 . C6 H5 2.150 . H41 H4 2.18(4) . C1 C5 2.216(4) . H2 H3 2.232 . C3 C7 2.236(4) . O2 O3 2.265(3) . O1 O5 2.267(2) . C1 C6 2.291(3) . H7 H9 2.293 . O5 C6 2.293(3) . O3 C2 2.313(2) . C2 C7 2.319(3) . O1 C5 2.326(3) . O2 C3 2.333(4) . O4 H3 2.333 . H5 H6a 2.336 . O4 C3 2.363(4) . O5 C2 2.374(3) . H1 H2 2.378 . C11 C13 2.389(4) . C10 C12 2.391(4) . C9 C11 2.397(3) . C9 C13 2.397(3) . O1 H13 2.400 . O3 C8 2.401(3) . C8 C10 2.402(4) . C8 C12 2.407(3) . H10 H11 2.410 . O2 C8 2.415(3) . H4 H6b 2.416 . H11 H12 2.418 . H12 H13 2.420 . H11 H13 2.421 2_556 O2 C1 2.421(3) . H9 H10 2.429 . O4 C5 2.429(3) . O5 C4 2.430(3) . O3 C4 2.433(3) . H41 H5 2.44(4) . O1 C2 2.442(2) . O3 H4 2.463 . H4 H5 2.477 . C7 C9 2.497(4) . C7 C13 2.507(3) . C9 H7 2.527 . C3 C5 2.527(3) . C1 C3 2.540(3) . O1 H7 2.540 1_554 C4 C6 2.542(3) . O5 H1 2.544 2_646 H3 H7 2.571 . H1 H7 2.572 1_554 O4 H1 2.581 2_646 C2 C4 2.593(4) . O4 H2 2.594 2_647 C4 H6b 2.596 . O4 H5 2.599 . C7 H3 2.610 . C3 H7 2.615 . H3 H4 2.619 . H9 H13 2.634 1_556 H6b H12 2.634 2_546 O5 H2 2.636 . H10 H12 2.639 1_556 C5 H41 2.64(4) . C7 H9 2.687 . C7 H13 2.690 . H5 H6b 2.696 . H41 H3 2.71(4) 2_647 C6 H4 2.740 . O2 H1 2.742 . O3 H6b 2.749 . H9 H11 2.750 2_547 H5 H9 2.756 1_544 C10 C13 2.763(4) . C9 C12 2.768(3) . O5 H6a 2.769 . H6a H9 2.771 1_544 C8 H4 2.772 1_565 C8 C11 2.773(4) . O2 H13 2.774 . O4 H3 2.782 2_647 H11 H12 2.786 2_556 O5 H2 2.791 2_646 H41 H1 2.80(4) 2_646 C7 H41 2.80(5) 1_565 O2 O4 2.803(3) 1_565 O1 O2 2.804(2) . O2 H3 2.808 . H6a H10 2.811 1_544 C2 C5 2.824(4) . O5 C3 2.832(3) . C9 H11 2.834 2_547 C2 H7 2.844 . H2 H5 2.845 2_656 C1 C4 2.858(4) . O3 H6a 2.873 1_556 C9 H4 2.883 1_565 O5 H3 2.884 1_554 O3 H13 2.907 . H41 H2 2.94(4) 2_647 O4 O5 2.939(3) . H6b H13 2.945 . O2 C13 2.947(3) . H41 H7 2.96(5) 1_545 C1 H6a 2.967 . C2 H41 2.98(5) 1_565 O1 C3 3.001(2) . C1 H7 3.011 1_554 H1 H3 3.017 1_554 O3 C13 3.019(3) . C1 H6b 3.023 . H6b H11 3.030 2_546 H1 H5 3.037 2_656 O1 O3 3.041(2) . C13 H4 3.043 1_565 C7 H2 3.048 . O5 H41 3.06(4) 2_656 C3 H6b 3.058 . H2 H3 3.061 2_657 C3 C6 3.065(3) . H12 H13 3.071 2_556 C4 H2 3.073 . H3 H6a 3.081 1_556 C12 H10 3.103 2_547 C12 H6b 3.103 2_556 H41 H2 3.12(5) 1_545 C9 H6a 3.119 1_566 O1 H11 3.121 2_546 C5 H1 3.127 2_646 C1 H5 3.127 . H9 H12 3.128 1_556 C13 H11 3.129 2_546 C6 H1 3.132 . C13 H10 3.132 2_547 C10 H6a 3.134 1_566 C5 H1 3.135 . O1 C4 3.146(3) . C2 C6 3.153(3) . O3 C6 3.153(3) . O3 H2 3.157 . O5 H6b 3.162 . O3 C1 3.172(2) . C3 H41 3.17(5) . C11 H10 3.175 2_547 O2 H4 3.186 1_565 C6 H13 3.190 . H6a H11 3.192 2_546 O1 H5 3.197 . O1 H9 3.204 1_554 C8 H41 3.22(4) 1_565 H41 H3 3.22(5) . H4 H6a 3.225 1_556 C8 H10 3.241 2_547 C1 H3 3.245 1_554 O2 H5 3.246 1_565 C10 H4 3.252 1_565 O3 C5 3.257(3) . C11 H13 3.268 2_556 C6 H11 3.274 2_546 C13 H9 3.274 1_554 C10 H12 3.275 1_556 C10 H10 3.284 2_547 O5 C2 3.287(3) 2_646 H2 H7 3.294 . C10 H11 3.294 2_547 C12 H11 3.299 2_546 O4 C2 3.302(4) . C11 H6b 3.303 2_556 C11 H12 3.303 2_556 O1 H3 3.307 1_554 O5 H4 3.312 . C9 H10 3.315 2_547 O1 C7 3.315(2) 1_554 O4 C2 3.317(2) 2_647 O1 H2 3.317 . O5 C1 3.317(3) 2_646 H4 H9 3.320 1_545 C13 H11 3.328 . C12 H10 3.329 . C11 H13 3.330 . C10 H12 3.333 . H6b H10 3.334 1_544 C11 H9 3.335 . C5 H2 3.336 2_646 C5 H3 3.336 . C9 H11 3.336 . C9 H13 3.336 . C8 H11 3.340 2_547 C4 H1 3.340 2_646 C13 H7 3.340 . C13 H9 3.341 . C13 H12 3.341 2_546 C8 H10 3.343 . O4 H2 3.345 . C8 H12 3.349 . C3 H6a 3.349 1_556 O1 O3 3.349(2) 1_554 C1 H3 3.352 . O1 C13 3.353(3) . C5 H2 3.374 . O5 H41 3.38(5) . C1 H13 3.390 . C4 H6a 3.390 . C2 H4 3.392 . C12 H4 3.394 1_565 C1 C7 3.398(3) . O1 C7 3.402(2) . C6 H9 3.403 1_544 C7 H4 3.406 1_565 C1 H41 3.41(4) 2_656 C3 H5 3.412 . H6a H7 3.415 1_554 O2 C4 3.415(4) 1_565 O4 C1 3.418(3) 2_646 C3 H1 3.431 . C12 H6b 3.444 1_565 O4 O5 3.446(3) 2_646 O3 C9 3.455(4) . C9 H13 3.462 1_556 C12 H10 3.476 1_554 O2 O5 3.479(2) 2_656 C5 H9 3.480 1_544 C11 H6a 3.485 2_556 O4 H7 3.487 2_647 H5 H13 3.490 1_545 C11 H4 3.491 1_565 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O4 H41 O2 1_555 1_555 1_545 .96(5) 1.86(5) 2.803(3) 167(4) yes C2 H2 O4 1_555 1_555 2_657 1.04 2.59 3.317(2) 126 yes C7 H7 O1 1_555 1_555 1_556 1.04 2.54 3.316(2) 131 yes C13 H13 O1 1_555 1_555 1_555 1.04 2.40 3.353(3) 152 yes C1 H1 O5 1_555 1_555 2_656 1.04 2.54 3.317(3) 131 yes C4 H4 Cg 1_555 1_555 1_545 1.04 2.83 3.843(3) 165 yes C10 H10 Cg 1_555 1_555 2_557 1.04 2.90 3.752(4) 140 yes 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_publ_flag C6 O1 C1 O5 23.2(2) ? C6 O1 C1 C2 -94.1(2) ? C6 O1 C1 H1 142.6 ? C1 O1 C6 C5 4.1(2) ? C1 O1 C6 H6a -114.9 ? C1 O1 C6 H6b 123.1 ? C7 O2 C2 C1 119.18(17) ? C7 O2 C2 C3 -1.4(2) yes C7 O2 C2 H2 -119.2 ? C2 O2 C7 O3 -23.7(2) yes C2 O2 C7 C8 -144.45(17) ? C2 O2 C7 H7 95.7 ? C7 O3 C3 C2 -40.1(2) yes C7 O3 C3 C4 -164.14(16) ? C7 O3 C3 H3 75.4 ? C3 O3 C7 O2 40.3(2) yes C3 O3 C7 C8 160.49(15) ? C3 O3 C7 H7 -79.1 ? H41 O4 C4 C3 167(3) ? H41 O4 C4 C5 -72(3) ? H41 O4 C4 H4 49(3) ? C5 O5 C1 O1 -41.93(18) ? C5 O5 C1 C2 78.22(18) ? C5 O5 C1 H1 -162.0 ? C1 O5 C5 C4 -77.4(2) ? C1 O5 C5 C6 42.8(2) ? C1 O5 C5 H5 162.7 ? O1 C1 C2 O2 -52.6(2) ? O1 C1 C2 C3 62.5(3) ? O1 C1 C2 H2 -177.1 ? O5 C1 C2 O2 -168.89(16) ? O5 C1 C2 C3 -53.8(2) ? O5 C1 C2 H2 66.6 ? H1 C1 C2 O2 71.3 ? H1 C1 C2 C3 -173.7 ? H1 C1 C2 H2 -53.3 ? O2 C2 C3 O3 25.2(2) yes O2 C2 C3 C4 145.31(16) ? O2 C2 C3 H3 -93.5 ? C1 C2 C3 O3 -93.4(2) ? C1 C2 C3 C4 26.7(2) ? C1 C2 C3 H3 147.9 ? H2 C2 C3 O3 146.3 ? H2 C2 C3 C4 -93.6 ? H2 C2 C3 H3 27.6 ? O3 C3 C4 O4 -147.96(17) ? O3 C3 C4 C5 91.2(2) ? O3 C3 C4 H4 -29.3 ? C2 C3 C4 O4 96.2(2) ? C2 C3 C4 C5 -24.6(2) ? C2 C3 C4 H4 -145.2 ? H3 C3 C4 O4 -24.9 ? H3 C3 C4 C5 -145.8 ? H3 C3 C4 H4 93.7 ? O4 C4 C5 O5 -68.4(3) ? O4 C4 C5 C6 178.8(2) ? O4 C4 C5 H5 51.6 ? C3 C4 C5 O5 49.8(2) ? C3 C4 C5 C6 -63.1(3) ? C3 C4 C5 H5 169.8 ? H4 C4 C5 O5 170.3 ? H4 C4 C5 C6 57.5 ? H4 C4 C5 H5 -69.7 ? O5 C5 C6 O1 -29.0(2) ? O5 C5 C6 H6a 90.2 ? O5 C5 C6 H6b -148.1 ? C4 C5 C6 O1 88.7(2) ? C4 C5 C6 H6a -152.0 ? C4 C5 C6 H6b -30.4 ? H5 C5 C6 O1 -146.2 ? H5 C5 C6 H6a -26.9 ? H5 C5 C6 H6b 94.70 ? O2 C7 C8 C9 -125.4(2) ? O2 C7 C8 C13 53.9(3) ? O3 C7 C8 C9 117.6(2) ? O3 C7 C8 C13 -63.1(3) ? H7 C7 C8 C9 -4.2 ? H7 C7 C8 C13 175.1 ? C7 C8 C9 C10 179.7(3) ? C7 C8 C9 H9 .1 ? C13 C8 C9 C10 .4(4) ? C13 C8 C9 H9 -179.2 ? C7 C8 C13 C12 -179.7(3) ? C7 C8 C13 H13 .4 ? C9 C8 C13 C12 -.4(4) ? C9 C8 C13 H13 179.7 ? C8 C9 C10 C11 .0(4) ? C8 C9 C10 H10 179.9 ? H9 C9 C10 C11 179.6(3) ? H9 C9 C10 H10 -.4 ? C9 C10 C11 C12 -.4(5) ? C9 C10 C11 H11 179.9 ? H10 C10 C11 C12 179.6 ? H10 C10 C11 H11 .0 ? C10 C11 C12 C13 .4(5) ? C10 C11 C12 H12 -179.7 ? H11 C11 C12 C13 -179.9 ? H11 C11 C12 H12 -.1 ? C11 C12 C13 C8 .0(5) ? C11 C12 C13 H13 179.9 ? H12 C12 C13 C8 -179.9 ? H12 C12 C13 H13 .1 ?