data_publication_text _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'Professor Shahriar Mobashery' _publ_contact_author_address ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; _publ_contact_author_email mobashery@nd.edu _publ_contact_author_phone 1(574)6312933 _publ_contact_author_fax 1(574)6316652 loop_ _publ_author_name _publ_author_address 'Hesek, Dusan' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Lee, Mijoon' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Zhang, Welie' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Noll, Bruce C.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; ' Mobashery, Shahriar' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; data_compound_6 # local ID: data_bcn320x5 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 1,6-Anhydro-2-iodo-4-O-benzyl-2-deoxy-\b-D-glucopyranose _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 I O4' _chemical_formula_sum 'C13 H15 I O4' _chemical_formula_weight 362.15 _chemical_absolute_configuration syn 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_int_tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.1718(4) _cell_length_b 7.5275(5) _cell_length_c 13.9663(6) _cell_angle_alpha 91.5770(10) _cell_angle_beta 92.433(5) _cell_angle_gamma 91.599(5) _cell_volume 647.74(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8849 _cell_measurement_theta_min 3.099 _cell_measurement_theta_max 35.385 _exptl_crystal_description block _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.857 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 2.476 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.54 _exptl_absorpt_correction_T_max 0.64 _exptl_absorpt_process_details 'Sheldrick, G. M. (2006). TWINABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFMO2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker d8 Apex II CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 8872 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0093 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 35.61 _reflns_number_total 8872 _reflns_number_gt 8850 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Bruker-Nonius AXS. (2007). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA. CCDC. (2005). enCIFer. The Cambridge Crystallographic Data Centre, Cambridge, UK. Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)' _refine_special_details ; Hydroxy hydrogens H3o were located by difference map and constrained to ride on the position of the parent atom. Displacement paramters for H atoms were set to 1.2\\times the equivalent isotropic U of the parent atom, 1.5\\times for hydroxy hydrogens. All non-hydrogen atoms were refined with parameters for anisotropic thermal motion. 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^)+(0.0387P)^2^+0.0316P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.016(10) _refine_ls_number_reflns 8872 _refine_ls_number_parameters 326 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0160 _refine_ls_R_factor_gt 0.0160 _refine_ls_wR_factor_ref 0.0584 _refine_ls_wR_factor_gt 0.0584 _refine_ls_goodness_of_fit_ref 1.303 _refine_ls_restrained_S_all 1.303 _refine_ls_shift/su_max 0.002 _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 I1_1 I 0.198032(11) 0.481121(10) 0.130628(8) 0.01409(3) Uani 1 1 d . . . O1_1 O -0.2149(2) 0.9316(2) 0.08863(11) 0.0141(3) Uani 1 1 d . . . O3_1 O 0.2559(3) 1.0525(2) 0.12203(11) 0.0132(3) Uani 1 1 d . . . H3O_1 H 0.1941 1.0436 0.0673 0.020 Uiso 1 1 calc R . . O4_1 O 0.1705(2) 0.8013(2) 0.33508(11) 0.0127(3) Uani 1 1 d . . . O5_1 O -0.1922(2) 0.7548(2) 0.21667(11) 0.0119(2) Uani 1 1 d . . . C1_1 C -0.1447(3) 0.7616(3) 0.11946(13) 0.0112(3) Uani 1 1 d . . . H1_1 H -0.2256 0.6640 0.0819 0.013 Uiso 1 1 calc R . . C2_1 C 0.1008(3) 0.7500(3) 0.10529(14) 0.0112(3) Uani 1 1 d . . . H2_1 H 0.1271 0.7758 0.0368 0.013 Uiso 1 1 calc R . . C3_1 C 0.2363(3) 0.8862(3) 0.16872(17) 0.0105(4) Uani 1 1 d . . . H3_1 H 0.3841 0.8392 0.1823 0.013 Uiso 1 1 calc R . . C4_1 C 0.1290(3) 0.9292(3) 0.26434(13) 0.0105(3) Uani 1 1 d . . . H4_1 H 0.1830 1.0487 0.2894 0.013 Uiso 1 1 calc R . . C5_1 C -0.1174(3) 0.9290(3) 0.25221(14) 0.0116(3) Uani 1 1 d . . . H5_1 H -0.1835 0.9591 0.3145 0.014 Uiso 1 1 calc R . . C6_1 C -0.2043(3) 1.0483(3) 0.17315(15) 0.0130(3) Uani 1 1 d . . . H6A_1 H -0.3497 1.0915 0.1876 0.016 Uiso 1 1 calc R . . H6B_1 H -0.1048 1.1516 0.1648 0.016 Uiso 1 1 calc R . . C7_1 C 0.3801(3) 0.8131(3) 0.38213(15) 0.0149(3) Uani 1 1 d . . . H7A_1 H 0.4361 0.9377 0.3836 0.018 Uiso 1 1 calc R . . H7B_1 H 0.4821 0.7388 0.3470 0.018 Uiso 1 1 calc R . . C8_1 C 0.3623(3) 0.7493(3) 0.48299(15) 0.0123(3) Uani 1 1 d . . . C9_1 C 0.1715(3) 0.7706(3) 0.53213(15) 0.0156(3) Uani 1 1 d . . . H9_1 H 0.0535 0.8299 0.5027 0.019 Uiso 1 1 calc R . . C10_1 C 0.1531(4) 0.7052(3) 0.62438(16) 0.0186(4) Uani 1 1 d . . . H10_1 H 0.0228 0.7203 0.6571 0.022 Uiso 1 1 calc R . . C11_1 C 0.3244(4) 0.6183(3) 0.66816(16) 0.0202(4) Uani 1 1 d . . . H11_1 H 0.3107 0.5718 0.7302 0.024 Uiso 1 1 calc R . . C12_1 C 0.5172(4) 0.5998(3) 0.62028(16) 0.0197(4) Uani 1 1 d . . . H12_1 H 0.6365 0.5434 0.6506 0.024 Uiso 1 1 calc R . . C13_1 C 0.5345(3) 0.6641(3) 0.52787(15) 0.0167(3) Uani 1 1 d . . . H13_1 H 0.6652 0.6495 0.4954 0.020 Uiso 1 1 calc R . . I1_2 I 0.806821(13) 0.521542(11) 0.870153(8) 0.01519(3) Uani 1 1 d . . . O1_2 O 0.4162(3) 0.0585(2) 0.93771(12) 0.0170(3) Uani 1 1 d . . . O3_2 O 0.8610(3) -0.0465(2) 0.89205(12) 0.0139(3) Uani 1 1 d . . . H3O_2 H 0.8219 -0.0340 0.9487 0.021 Uiso 1 1 calc R . . O4_2 O 0.7075(2) 0.1882(2) 0.67738(10) 0.0138(3) Uani 1 1 d . . . O5_2 O 0.3865(2) 0.2339(2) 0.80923(11) 0.0144(3) Uani 1 1 d . . . C1_2 C 0.4720(3) 0.2317(3) 0.90375(15) 0.0148(3) Uani 1 1 d . . . H1_2 H 0.4072 0.3266 0.9441 0.018 Uiso 1 1 calc R . . C2_2 C 0.7202(3) 0.2526(3) 0.90713(14) 0.0127(3) Uani 1 1 d . . . H2_2 H 0.7743 0.2347 0.9746 0.015 Uiso 1 1 calc R . . C3_2 C 0.8255(3) 0.1142(3) 0.84210(17) 0.0114(4) Uani 1 1 d . . . H3_2 H 0.9684 0.1636 0.8223 0.014 Uiso 1 1 calc R . . C4_2 C 0.6833(3) 0.0648(3) 0.75162(13) 0.0107(3) Uani 1 1 d . . . H4_2 H 0.7227 -0.0557 0.7273 0.013 Uiso 1 1 calc R . . C5_2 C 0.4424(3) 0.0621(3) 0.77184(15) 0.0130(3) Uani 1 1 d . . . H5_2 H 0.3528 0.0300 0.7122 0.016 Uiso 1 1 calc R . . C6_2 C 0.3806(3) -0.0581(3) 0.85377(16) 0.0150(4) Uani 1 1 d . . . H6A_2 H 0.2271 -0.0998 0.8463 0.018 Uiso 1 1 calc R . . H6B_2 H 0.4745 -0.1624 0.8572 0.018 Uiso 1 1 calc R . . C7_2 C 0.9003(3) 0.1735(3) 0.62557(16) 0.0187(4) Uani 1 1 d . . . H7A_2 H 0.9434 0.0479 0.6219 0.022 Uiso 1 1 calc R . . H7B_2 H 1.0199 0.2447 0.6586 0.022 Uiso 1 1 calc R . . C8_2 C 0.8572(3) 0.2408(3) 0.52619(15) 0.0147(3) Uani 1 1 d . . . C9_2 C 0.6527(3) 0.2207(3) 0.48074(17) 0.0169(4) Uani 1 1 d . . . H9_2 H 0.5393 0.1604 0.5117 0.020 Uiso 1 1 calc R . . C10_2 C 0.6134(4) 0.2885(3) 0.38984(16) 0.0194(4) Uani 1 1 d . . . H10_2 H 0.4729 0.2760 0.3595 0.023 Uiso 1 1 calc R . . C11_2 C 0.7803(4) 0.3747(3) 0.34351(16) 0.0195(4) Uani 1 1 d . . . H11_2 H 0.7536 0.4210 0.2817 0.023 Uiso 1 1 calc R . . C12_2 C 0.9858(4) 0.3928(3) 0.38783(17) 0.0216(4) Uani 1 1 d . . . H12_2 H 1.1001 0.4503 0.3561 0.026 Uiso 1 1 calc R . . C13_2 C 1.0240(3) 0.3264(3) 0.47902(16) 0.0184(4) Uani 1 1 d . . . H13_2 H 1.1644 0.3395 0.5093 0.022 Uiso 1 1 calc R . . 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 I1_1 0.02035(5) 0.00960(6) 0.01276(6) 0.00110(5) 0.00398(4) 0.00259(4) O1_1 0.0198(6) 0.0125(7) 0.0100(6) 0.0016(5) -0.0013(5) 0.0031(5) O3_1 0.0170(6) 0.0102(6) 0.0128(6) 0.0038(5) 0.0042(5) -0.0011(4) O4_1 0.0139(5) 0.0133(7) 0.0105(6) 0.0038(5) -0.0028(5) -0.0035(4) O5_1 0.0133(5) 0.0120(6) 0.0103(6) 0.0008(5) 0.0007(4) -0.0027(4) C1_1 0.0143(6) 0.0097(8) 0.0095(7) -0.0005(6) -0.0008(5) -0.0009(5) C2_1 0.0166(6) 0.0076(8) 0.0094(7) 0.0000(6) 0.0018(5) 0.0011(5) C3_1 0.0120(7) 0.0083(8) 0.0114(8) 0.0026(6) 0.0023(6) -0.0001(6) C4_1 0.0106(6) 0.0126(8) 0.0084(7) 0.0018(6) 0.0000(5) -0.0006(5) C5_1 0.0126(6) 0.0129(8) 0.0094(7) 0.0002(6) 0.0016(5) -0.0004(5) C6_1 0.0137(6) 0.0130(9) 0.0123(8) 0.0015(7) 0.0000(6) 0.0020(5) C7_1 0.0136(6) 0.0178(9) 0.0131(8) 0.0042(7) -0.0009(6) -0.0018(6) C8_1 0.0157(6) 0.0117(9) 0.0094(8) 0.0000(7) -0.0018(6) 0.0014(6) C9_1 0.0187(7) 0.0170(10) 0.0114(8) 0.0025(7) 0.0004(6) 0.0037(6) C10_1 0.0251(8) 0.0187(10) 0.0123(8) 0.0001(7) 0.0033(7) 0.0025(7) C11_1 0.0342(10) 0.0157(10) 0.0107(8) 0.0005(7) -0.0027(8) 0.0029(8) C12_1 0.0288(9) 0.0163(10) 0.0135(9) -0.0007(8) -0.0063(7) 0.0058(7) C13_1 0.0189(7) 0.0173(10) 0.0137(8) -0.0010(7) -0.0043(6) 0.0036(6) I1_2 0.02351(6) 0.01049(6) 0.01124(6) 0.00125(5) -0.00254(4) -0.00139(4) O1_2 0.0221(6) 0.0159(7) 0.0136(7) 0.0046(6) 0.0071(5) 0.0001(5) O3_2 0.0175(6) 0.0131(7) 0.0117(6) 0.0050(5) 0.0029(5) 0.0033(5) O4_2 0.0165(5) 0.0168(7) 0.0089(6) 0.0040(5) 0.0046(4) 0.0044(5) O5_2 0.0144(5) 0.0143(7) 0.0149(6) 0.0030(5) 0.0021(4) 0.0038(4) C1_2 0.0177(7) 0.0146(9) 0.0129(8) 0.0020(7) 0.0064(6) 0.0037(6) C2_2 0.0189(7) 0.0103(8) 0.0089(7) 0.0012(6) 0.0011(6) 0.0012(6) C3_2 0.0115(7) 0.0112(8) 0.0120(8) 0.0032(7) 0.0019(6) 0.0027(6) C4_2 0.0132(6) 0.0101(8) 0.0092(7) 0.0007(6) 0.0021(5) 0.0011(5) C5_2 0.0123(6) 0.0128(9) 0.0138(8) 0.0012(7) 0.0000(5) -0.0003(5) C6_2 0.0133(6) 0.0142(9) 0.0180(9) 0.0033(7) 0.0033(6) -0.0002(6) C7_2 0.0179(7) 0.0272(12) 0.0124(9) 0.0077(8) 0.0075(7) 0.0061(7) C8_2 0.0207(7) 0.0137(9) 0.0101(8) 0.0004(7) 0.0041(6) 0.0009(6) C9_2 0.0221(8) 0.0171(10) 0.0117(8) 0.0011(8) 0.0043(7) -0.0010(7) C10_2 0.0288(9) 0.0178(10) 0.0116(8) 0.0019(8) 0.0001(7) -0.0006(7) C11_2 0.0372(11) 0.0128(9) 0.0086(8) 0.0001(7) 0.0031(8) -0.0015(8) C12_2 0.0329(10) 0.0188(11) 0.0131(9) 0.0018(8) 0.0075(7) -0.0070(8) C13_2 0.0235(8) 0.0189(10) 0.0132(8) 0.0020(7) 0.0059(7) -0.0023(7) _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 I1_1 C2_1 2.1615(19) . ? O1_1 C1_1 1.434(2) . ? O1_1 C6_1 1.450(3) . ? O3_1 C3_1 1.432(3) . ? O3_1 H3O_1 0.8400 . ? O4_1 C4_1 1.419(2) . ? O4_1 C7_1 1.425(2) . ? O5_1 C1_1 1.403(2) . ? O5_1 C5_1 1.446(3) . ? C1_1 C2_1 1.541(2) . ? C1_1 H1_1 1.0000 . ? C2_1 C3_1 1.541(3) . ? C2_1 H2_1 1.0000 . ? C3_1 C4_1 1.546(3) . ? C3_1 H3_1 1.0000 . ? C4_1 C5_1 1.523(2) . ? C4_1 H4_1 1.0000 . ? C5_1 C6_1 1.531(3) . ? C5_1 H5_1 1.0000 . ? C6_1 H6A_1 0.9900 . ? C6_1 H6B_1 0.9900 . ? C7_1 C8_1 1.508(3) . ? C7_1 H7A_1 0.9900 . ? C7_1 H7B_1 0.9900 . ? C8_1 C13_1 1.392(3) . ? C8_1 C9_1 1.399(3) . ? C9_1 C10_1 1.400(3) . ? C9_1 H9_1 0.9500 . ? C10_1 C11_1 1.387(3) . ? C10_1 H10_1 0.9500 . ? C11_1 C12_1 1.398(3) . ? C11_1 H11_1 0.9500 . ? C12_1 C13_1 1.398(3) . ? C12_1 H12_1 0.9500 . ? C13_1 H13_1 0.9500 . ? I1_2 C2_2 2.1612(19) . ? O1_2 C1_2 1.437(3) . ? O1_2 C6_2 1.451(3) . ? O3_2 C3_2 1.430(3) . ? O3_2 H3O_2 0.8400 . ? O4_2 C4_2 1.421(2) . ? O4_2 C7_2 1.424(2) . ? O5_2 C1_2 1.401(3) . ? O5_2 C5_2 1.438(3) . ? C1_2 C2_2 1.534(3) . ? C1_2 H1_2 1.0000 . ? C2_2 C3_2 1.539(3) . ? C2_2 H2_2 1.0000 . ? C3_2 C4_2 1.539(3) . ? C3_2 H3_2 1.0000 . ? C4_2 C5_2 1.525(2) . ? C4_2 H4_2 1.0000 . ? C5_2 C6_2 1.533(3) . ? C5_2 H5_2 1.0000 . ? C6_2 H6A_2 0.9900 . ? C6_2 H6B_2 0.9900 . ? C7_2 C8_2 1.506(3) . ? C7_2 H7A_2 0.9900 . ? C7_2 H7B_2 0.9900 . ? C8_2 C9_2 1.390(3) . ? C8_2 C13_2 1.398(3) . ? C9_2 C10_2 1.396(3) . ? C9_2 H9_2 0.9500 . ? C10_2 C11_2 1.394(3) . ? C10_2 H10_2 0.9500 . ? C11_2 C12_2 1.389(4) . ? C11_2 H11_2 0.9500 . ? C12_2 C13_2 1.394(3) . ? C12_2 H12_2 0.9500 . ? C13_2 H13_2 0.9500 . ? 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_1 O1_1 C6_1 106.42(14) . . ? C3_1 O3_1 H3O_1 109.5 . . ? C4_1 O4_1 C7_1 115.89(14) . . ? C1_1 O5_1 C5_1 101.81(13) . . ? O5_1 C1_1 O1_1 105.61(16) . . ? O5_1 C1_1 C2_1 111.53(14) . . ? O1_1 C1_1 C2_1 108.65(14) . . ? O5_1 C1_1 H1_1 110.3 . . ? O1_1 C1_1 H1_1 110.3 . . ? C2_1 C1_1 H1_1 110.3 . . ? C3_1 C2_1 C1_1 112.79(16) . . ? C3_1 C2_1 I1_1 111.59(12) . . ? C1_1 C2_1 I1_1 108.80(11) . . ? C3_1 C2_1 H2_1 107.8 . . ? C1_1 C2_1 H2_1 107.8 . . ? I1_1 C2_1 H2_1 107.8 . . ? O3_1 C3_1 C2_1 110.71(18) . . ? O3_1 C3_1 C4_1 105.44(18) . . ? C2_1 C3_1 C4_1 112.30(15) . . ? O3_1 C3_1 H3_1 109.4 . . ? C2_1 C3_1 H3_1 109.4 . . ? C4_1 C3_1 H3_1 109.4 . . ? O4_1 C4_1 C5_1 104.35(13) . . ? O4_1 C4_1 C3_1 113.04(16) . . ? C5_1 C4_1 C3_1 111.88(16) . . ? O4_1 C4_1 H4_1 109.1 . . ? C5_1 C4_1 H4_1 109.1 . . ? C3_1 C4_1 H4_1 109.1 . . ? O5_1 C5_1 C4_1 108.28(15) . . ? O5_1 C5_1 C6_1 101.73(15) . . ? C4_1 C5_1 C6_1 114.56(14) . . ? O5_1 C5_1 H5_1 110.6 . . ? C4_1 C5_1 H5_1 110.6 . . ? C6_1 C5_1 H5_1 110.6 . . ? O1_1 C6_1 C5_1 103.31(16) . . ? O1_1 C6_1 H6A_1 111.1 . . ? C5_1 C6_1 H6A_1 111.1 . . ? O1_1 C6_1 H6B_1 111.1 . . ? C5_1 C6_1 H6B_1 111.1 . . ? H6A_1 C6_1 H6B_1 109.1 . . ? O4_1 C7_1 C8_1 108.71(14) . . ? O4_1 C7_1 H7A_1 109.9 . . ? C8_1 C7_1 H7A_1 109.9 . . ? O4_1 C7_1 H7B_1 109.9 . . ? C8_1 C7_1 H7B_1 109.9 . . ? H7A_1 C7_1 H7B_1 108.3 . . ? C13_1 C8_1 C9_1 118.88(19) . . ? C13_1 C8_1 C7_1 120.31(18) . . ? C9_1 C8_1 C7_1 120.79(16) . . ? C8_1 C9_1 C10_1 120.53(18) . . ? C8_1 C9_1 H9_1 119.7 . . ? C10_1 C9_1 H9_1 119.7 . . ? C11_1 C10_1 C9_1 120.3(2) . . ? C11_1 C10_1 H10_1 119.9 . . ? C9_1 C10_1 H10_1 119.9 . . ? C10_1 C11_1 C12_1 119.5(2) . . ? C10_1 C11_1 H11_1 120.2 . . ? C12_1 C11_1 H11_1 120.2 . . ? C11_1 C12_1 C13_1 120.07(19) . . ? C11_1 C12_1 H12_1 120.0 . . ? C13_1 C12_1 H12_1 120.0 . . ? C8_1 C13_1 C12_1 120.7(2) . . ? C8_1 C13_1 H13_1 119.6 . . ? C12_1 C13_1 H13_1 119.6 . . ? C1_2 O1_2 C6_2 106.85(15) . . ? C3_2 O3_2 H3O_2 109.5 . . ? C4_2 O4_2 C7_2 115.39(14) . . ? C1_2 O5_2 C5_2 102.25(14) . . ? O5_2 C1_2 O1_2 105.60(17) . . ? O5_2 C1_2 C2_2 111.08(15) . . ? O1_2 C1_2 C2_2 108.07(15) . . ? O5_2 C1_2 H1_2 110.6 . . ? O1_2 C1_2 H1_2 110.6 . . ? C2_2 C1_2 H1_2 110.6 . . ? C1_2 C2_2 C3_2 112.23(18) . . ? C1_2 C2_2 I1_2 108.58(12) . . ? C3_2 C2_2 I1_2 111.95(13) . . ? C1_2 C2_2 H2_2 108.0 . . ? C3_2 C2_2 H2_2 108.0 . . ? I1_2 C2_2 H2_2 108.0 . . ? O3_2 C3_2 C4_2 107.14(19) . . ? O3_2 C3_2 C2_2 110.64(17) . . ? C4_2 C3_2 C2_2 112.36(15) . . ? O3_2 C3_2 H3_2 108.9 . . ? C4_2 C3_2 H3_2 108.9 . . ? C2_2 C3_2 H3_2 108.9 . . ? O4_2 C4_2 C5_2 105.26(14) . . ? O4_2 C4_2 C3_2 112.87(16) . . ? C5_2 C4_2 C3_2 111.85(16) . . ? O4_2 C4_2 H4_2 108.9 . . ? C5_2 C4_2 H4_2 108.9 . . ? C3_2 C4_2 H4_2 108.9 . . ? O5_2 C5_2 C4_2 109.03(15) . . ? O5_2 C5_2 C6_2 101.49(16) . . ? C4_2 C5_2 C6_2 114.13(15) . . ? O5_2 C5_2 H5_2 110.6 . . ? C4_2 C5_2 H5_2 110.6 . . ? C6_2 C5_2 H5_2 110.6 . . ? O1_2 C6_2 C5_2 102.67(17) . . ? O1_2 C6_2 H6A_2 111.2 . . ? C5_2 C6_2 H6A_2 111.2 . . ? O1_2 C6_2 H6B_2 111.2 . . ? C5_2 C6_2 H6B_2 111.2 . . ? H6A_2 C6_2 H6B_2 109.1 . . ? O4_2 C7_2 C8_2 108.53(16) . . ? O4_2 C7_2 H7A_2 110.0 . . ? C8_2 C7_2 H7A_2 110.0 . . ? O4_2 C7_2 H7B_2 110.0 . . ? C8_2 C7_2 H7B_2 110.0 . . ? H7A_2 C7_2 H7B_2 108.4 . . ? C9_2 C8_2 C13_2 119.28(19) . . ? C9_2 C8_2 C7_2 120.99(18) . . ? C13_2 C8_2 C7_2 119.72(19) . . ? C8_2 C9_2 C10_2 120.35(19) . . ? C8_2 C9_2 H9_2 119.8 . . ? C10_2 C9_2 H9_2 119.8 . . ? C11_2 C10_2 C9_2 120.0(2) . . ? C11_2 C10_2 H10_2 120.0 . . ? C9_2 C10_2 H10_2 120.0 . . ? C12_2 C11_2 C10_2 120.0(2) . . ? C12_2 C11_2 H11_2 120.0 . . ? C10_2 C11_2 H11_2 120.0 . . ? C11_2 C12_2 C13_2 119.88(19) . . ? C11_2 C12_2 H12_2 120.1 . . ? C13_2 C12_2 H12_2 120.1 . . ? C12_2 C13_2 C8_2 120.5(2) . . ? C12_2 C13_2 H13_2 119.7 . . ? C8_2 C13_2 H13_2 119.7 . . ? 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 C5_1 O5_1 C1_1 O1_1 -44.50(16) . . . . ? C5_1 O5_1 C1_1 C2_1 73.35(17) . . . . ? C6_1 O1_1 C1_1 O5_1 26.55(17) . . . . ? C6_1 O1_1 C1_1 C2_1 -93.22(17) . . . . ? O5_1 C1_1 C2_1 C3_1 -51.7(2) . . . . ? O1_1 C1_1 C2_1 C3_1 64.3(2) . . . . ? O5_1 C1_1 C2_1 I1_1 72.66(17) . . . . ? O1_1 C1_1 C2_1 I1_1 -171.33(12) . . . . ? C1_1 C2_1 C3_1 O3_1 -86.89(19) . . . . ? I1_1 C2_1 C3_1 O3_1 150.28(13) . . . . ? C1_1 C2_1 C3_1 C4_1 30.7(2) . . . . ? I1_1 C2_1 C3_1 C4_1 -92.16(16) . . . . ? C7_1 O4_1 C4_1 C5_1 -160.92(17) . . . . ? C7_1 O4_1 C4_1 C3_1 77.3(2) . . . . ? O3_1 C3_1 C4_1 O4_1 -157.24(16) . . . . ? C2_1 C3_1 C4_1 O4_1 82.11(19) . . . . ? O3_1 C3_1 C4_1 C5_1 85.3(2) . . . . ? C2_1 C3_1 C4_1 C5_1 -35.3(2) . . . . ? C1_1 O5_1 C5_1 C4_1 -77.32(16) . . . . ? C1_1 O5_1 C5_1 C6_1 43.72(15) . . . . ? O4_1 C4_1 C5_1 O5_1 -62.99(18) . . . . ? C3_1 C4_1 C5_1 O5_1 59.56(19) . . . . ? O4_1 C4_1 C5_1 C6_1 -175.71(17) . . . . ? C3_1 C4_1 C5_1 C6_1 -53.2(2) . . . . ? C1_1 O1_1 C6_1 C5_1 1.33(17) . . . . ? O5_1 C5_1 C6_1 O1_1 -27.42(16) . . . . ? C4_1 C5_1 C6_1 O1_1 89.13(19) . . . . ? C4_1 O4_1 C7_1 C8_1 149.24(18) . . . . ? O4_1 C7_1 C8_1 C13_1 148.0(2) . . . . ? O4_1 C7_1 C8_1 C9_1 -30.5(3) . . . . ? C13_1 C8_1 C9_1 C10_1 -0.8(3) . . . . ? C7_1 C8_1 C9_1 C10_1 177.6(2) . . . . ? C8_1 C9_1 C10_1 C11_1 0.0(4) . . . . ? C9_1 C10_1 C11_1 C12_1 1.3(4) . . . . ? C10_1 C11_1 C12_1 C13_1 -1.8(4) . . . . ? C9_1 C8_1 C13_1 C12_1 0.4(3) . . . . ? C7_1 C8_1 C13_1 C12_1 -178.1(2) . . . . ? C11_1 C12_1 C13_1 C8_1 0.9(4) . . . . ? C5_2 O5_2 C1_2 O1_2 -43.07(16) . . . . ? C5_2 O5_2 C1_2 C2_2 73.85(18) . . . . ? C6_2 O1_2 C1_2 O5_2 23.03(18) . . . . ? C6_2 O1_2 C1_2 C2_2 -95.91(18) . . . . ? O5_2 C1_2 C2_2 C3_2 -54.0(2) . . . . ? O1_2 C1_2 C2_2 C3_2 61.4(2) . . . . ? O5_2 C1_2 C2_2 I1_2 70.31(19) . . . . ? O1_2 C1_2 C2_2 I1_2 -174.29(13) . . . . ? C1_2 C2_2 C3_2 O3_2 -86.6(2) . . . . ? I1_2 C2_2 C3_2 O3_2 150.97(14) . . . . ? C1_2 C2_2 C3_2 C4_2 33.1(2) . . . . ? I1_2 C2_2 C3_2 C4_2 -89.33(17) . . . . ? C7_2 O4_2 C4_2 C5_2 -161.05(18) . . . . ? C7_2 O4_2 C4_2 C3_2 76.7(2) . . . . ? O3_2 C3_2 C4_2 O4_2 -155.58(15) . . . . ? C2_2 C3_2 C4_2 O4_2 82.70(19) . . . . ? O3_2 C3_2 C4_2 C5_2 85.95(19) . . . . ? C2_2 C3_2 C4_2 C5_2 -35.8(2) . . . . ? C1_2 O5_2 C5_2 C4_2 -75.89(17) . . . . ? C1_2 O5_2 C5_2 C6_2 44.87(16) . . . . ? O4_2 C4_2 C5_2 O5_2 -64.84(19) . . . . ? C3_2 C4_2 C5_2 O5_2 58.1(2) . . . . ? O4_2 C4_2 C5_2 C6_2 -177.52(17) . . . . ? C3_2 C4_2 C5_2 C6_2 -54.6(2) . . . . ? C1_2 O1_2 C6_2 C5_2 5.06(18) . . . . ? O5_2 C5_2 C6_2 O1_2 -30.30(17) . . . . ? C4_2 C5_2 C6_2 O1_2 86.8(2) . . . . ? C4_2 O4_2 C7_2 C8_2 152.78(18) . . . . ? O4_2 C7_2 C8_2 C9_2 -32.3(3) . . . . ? O4_2 C7_2 C8_2 C13_2 147.0(2) . . . . ? C13_2 C8_2 C9_2 C10_2 -1.3(4) . . . . ? C7_2 C8_2 C9_2 C10_2 178.0(2) . . . . ? C8_2 C9_2 C10_2 C11_2 1.0(4) . . . . ? C9_2 C10_2 C11_2 C12_2 0.1(4) . . . . ? C10_2 C11_2 C12_2 C13_2 -0.7(4) . . . . ? C11_2 C12_2 C13_2 C8_2 0.3(4) . . . . ? C9_2 C8_2 C13_2 C12_2 0.7(4) . . . . ? C7_2 C8_2 C13_2 C12_2 -178.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_distance_DA _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O3_1 H3O_1 0.840 2.319 116.57 2.798(2) O1_2 1_564 ? O3_2 H3O_2 0.840 2.000 162.54 2.813(2) O1_1 1_646 ? C1_1 H1_1 1.000 3.134 131.94 3.8747(19) I1_2 1_454 ? C1_2 H1_2 1.000 3.164 154.64 4.090(2) I1_1 1_556 ? _diffrn_measured_fraction_theta_max 0.829 _diffrn_reflns_theta_full 35.61 _diffrn_measured_fraction_theta_full 0.829 _refine_diff_density_max 0.774 _refine_diff_density_min -0.719 _refine_diff_density_rms 0.143 _chemical_compound_source synthesized