#------------------------------------------------------------------------------ #$Date: 2011-06-22 00:13:35 +0300 (Wed, 22 Jun 2011) $ #$Revision: 21261 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7151773.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7151773 loop_ _publ_author_name 'Schanderl, Martin' 'Jeong, Won Boo' 'Schwarz, Michael' 'Reiser, Oliver' _publ_section_title ; Stereoselective rearrangement of guaianolides to tricyclic \d-valerolactones. ; _journal_issue 7 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 2543 _journal_page_last 2547 _journal_volume 9 _journal_year 2011 _chemical_absolute_configuration unk _chemical_compound_source 'see text' _chemical_formula_moiety 'C14 H18 O3' _chemical_formula_sum 'C14 H18 O3' _chemical_formula_weight 234.28 _chemical_name_systematic ; ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90.202(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.2097(7) _cell_length_b 13.1829(14) _cell_length_c 15.2549(18) _cell_measurement_reflns_used 3469 _cell_measurement_temperature 297 _cell_measurement_theta_max 25.91 _cell_measurement_theta_min 2.04 _cell_volume 1248.8(2) _computing_cell_refinement 'STOE (1998)' _computing_data_collection 'STOE (1998)' _computing_data_reduction 'STOE (1998)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR-97 (Altomare, 1999)' _diffrn_ambient_temperature 297(1) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'STOE-IPDS diffractometer' _diffrn_measurement_method rotation _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0980 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 9892 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.91 _diffrn_reflns_theta_max 25.91 _diffrn_reflns_theta_min 2.04 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description stick _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.140 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.027 _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.6(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.781 _refine_ls_hydrogen_treatment ref _refine_ls_matrix_type full _refine_ls_number_parameters 313 _refine_ls_number_reflns 4794 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.781 _refine_ls_R_factor_all 0.1263 _refine_ls_R_factor_gt 0.0456 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.0969 _reflns_number_gt 2066 _reflns_number_total 4794 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file c0ob00919a.txt _[local]_cod_data_source_block i072 _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_database_code 7151773 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z 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 O1 0.1002(19) 0.0530(15) 0.118(2) -0.0065(16) 0.0344(18) -0.0059(15) O2 0.113(2) 0.0740(19) 0.183(3) -0.007(2) 0.064(2) -0.0237(17) O3 0.114(2) 0.0662(18) 0.084(2) -0.0189(18) -0.0072(17) -0.0105(18) C1 0.082(3) 0.051(3) 0.116(4) 0.011(3) 0.039(3) 0.001(2) C2 0.069(2) 0.054(3) 0.058(2) 0.0058(19) 0.0066(19) 0.0081(19) C3 0.082(3) 0.081(3) 0.089(3) -0.012(2) 0.024(2) 0.001(2) C4 0.055(2) 0.044(2) 0.061(2) 0.0013(17) -0.0045(17) 0.0076(17) C5 0.060(2) 0.053(2) 0.058(2) 0.0088(19) -0.0024(17) 0.0075(17) C6 0.079(2) 0.049(2) 0.075(3) 0.0011(19) 0.020(2) 0.0061(18) C7 0.128(4) 0.057(3) 0.089(3) -0.010(2) 0.017(3) 0.001(3) C8 0.148(4) 0.075(3) 0.073(3) -0.011(2) 0.033(3) 0.012(3) C9 0.118(3) 0.082(3) 0.064(3) 0.011(2) 0.024(2) 0.007(3) C10 0.081(2) 0.052(2) 0.057(2) 0.0096(19) 0.0084(19) 0.000(2) C11 0.062(2) 0.073(3) 0.066(3) 0.008(2) 0.0037(19) 0.007(2) C12 0.073(3) 0.115(4) 0.101(4) 0.033(3) 0.009(2) -0.011(3) C13 0.063(2) 0.077(3) 0.083(3) 0.019(3) -0.009(2) -0.011(2) C14 0.073(2) 0.060(2) 0.057(2) -0.0087(19) -0.0124(18) 0.0007(17) O4 0.0810(18) 0.0718(18) 0.104(2) 0.0059(17) 0.0181(17) 0.0207(15) O5 0.149(3) 0.119(3) 0.134(3) 0.002(2) 0.068(3) 0.053(2) O6 0.106(2) 0.0772(18) 0.082(2) 0.0224(17) -0.0029(16) -0.0071(16) C15 0.081(3) 0.091(4) 0.087(3) 0.002(3) 0.013(3) 0.010(3) C16 0.060(2) 0.076(3) 0.059(2) 0.005(2) 0.005(2) 0.000(2) C17 0.095(3) 0.139(4) 0.092(3) 0.020(3) 0.012(3) 0.011(3) C18 0.060(2) 0.061(2) 0.053(2) -0.0047(18) -0.0064(18) -0.0008(18) C19 0.058(2) 0.053(2) 0.057(2) 0.0008(18) -0.0035(17) -0.0006(17) C20 0.063(2) 0.072(3) 0.072(3) 0.004(2) -0.001(2) -0.0002(19) C21 0.084(3) 0.076(3) 0.093(3) 0.024(2) -0.008(3) 0.002(2) C22 0.101(3) 0.112(4) 0.077(3) 0.036(3) 0.009(3) 0.005(3) C23 0.084(3) 0.105(3) 0.076(3) 0.017(3) 0.010(2) -0.001(2) C24 0.055(2) 0.069(3) 0.060(2) -0.003(2) -0.0013(17) -0.0060(19) C25 0.051(2) 0.071(3) 0.069(3) -0.023(2) -0.0013(19) -0.002(2) C26 0.064(2) 0.093(3) 0.104(3) -0.027(3) -0.001(2) 0.000(2) C27 0.067(2) 0.062(3) 0.090(3) -0.014(2) -0.008(2) 0.0119(19) C28 0.065(2) 0.066(2) 0.068(2) 0.007(2) -0.0028(19) -0.0041(19) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags O1 O Uani 0.0739(5) 0.14906(18) 0.4391(2) 1.000 0.0903(10) . . O2 O Uani -0.1947(5) 0.1845(2) 0.5252(3) 1.000 0.1232(14) . . O3 O Uani 0.3373(5) 0.4984(2) 0.5489(2) 1.000 0.0881(11) . . C1 C Uani -0.0233(7) 0.2115(3) 0.4953(4) 1.000 0.0829(19) . . C2 C Uani 0.0757(6) 0.3120(3) 0.5174(2) 1.000 0.0603(14) . . C3 C Uani -0.0310(6) 0.3666(3) 0.5730(3) 1.000 0.0839(17) . . C4 C Uani 0.2811(5) 0.3396(2) 0.4729(2) 1.000 0.0533(12) . . C5 C Uani 0.2816(5) 0.2907(2) 0.3822(2) 1.000 0.0570(12) . . C6 C Uani 0.2725(6) 0.1758(2) 0.3958(2) 1.000 0.0676(14) . . C7 C Uani 0.2803(7) 0.1164(3) 0.3118(3) 1.000 0.0913(19) . . C8 C Uani 0.4783(8) 0.1446(3) 0.2608(3) 1.000 0.0986(19) . . C9 C Uani 0.4829(7) 0.2571(3) 0.2420(3) 1.000 0.0879(17) . . C10 C Uani 0.4653(6) 0.3214(3) 0.3231(2) 1.000 0.0633(12) . . C11 C Uani 0.5824(6) 0.4025(3) 0.3406(3) 1.000 0.0670(16) . . C12 C Uani 0.7631(6) 0.4412(4) 0.2835(3) 1.000 0.096(2) . . C13 C Uani 0.5413(5) 0.4690(3) 0.4177(3) 1.000 0.0744(16) . . C14 C Uani 0.3280(5) 0.4514(3) 0.4644(2) 1.000 0.0634(12) . . O4 O Uani 0.0388(4) 0.34294(19) -0.0738(2) 1.000 0.0856(11) . . O5 O Uani -0.1375(6) 0.3413(3) 0.0481(2) 1.000 0.1338(17) . . O6 O Uani 0.3429(5) 0.0064(2) 0.05898(19) 1.000 0.0884(11) . . C15 C Uani -0.0120(7) 0.2961(3) 0.0016(3) 1.000 0.0863(19) . . C16 C Uani 0.0825(5) 0.1954(3) 0.0224(3) 1.000 0.0650(14) . . C17 C Uani -0.0004(7) 0.1521(4) 0.0915(3) 1.000 0.1086(19) . . C18 C Uani 0.2499(5) 0.1501(3) -0.0380(2) 1.000 0.0580(12) . . C19 C Uani 0.3557(5) 0.2355(3) -0.0901(2) 1.000 0.0560(12) . . C20 C Uani 0.1816(6) 0.2928(3) -0.1373(2) 1.000 0.0690(16) . . C21 C Uani 0.2587(6) 0.3746(3) -0.1980(3) 1.000 0.0844(17) . . C22 C Uani 0.4085(7) 0.3263(4) -0.2656(3) 1.000 0.0967(19) . . C23 C Uani 0.5966(7) 0.2765(3) -0.2193(3) 1.000 0.0883(17) . . C24 C Uani 0.5273(5) 0.1967(3) -0.1527(2) 1.000 0.0613(14) . . C25 C Uani 0.6152(5) 0.1061(3) -0.1435(2) 1.000 0.0637(16) . . C26 C Uani 0.7770(6) 0.0617(3) -0.2065(3) 1.000 0.0870(16) . . C27 C Uani 0.5570(6) 0.0369(3) -0.0693(3) 1.000 0.0730(16) . . C28 C Uani 0.4197(5) 0.0824(3) 0.0016(2) 1.000 0.0663(12) . . H3A H Uiso 0.01960 0.43040 0.58890 1.000 0.1010 calc R H3B H Uiso -0.15820 0.34200 0.59690 1.000 0.1010 calc R H3O H Uiso 0.326(7) 0.554(3) 0.535(3) 1.000 0.1060 . . H4 H Uiso 0.39910 0.30920 0.50670 1.000 0.0640 calc R H5 H Uiso 0.14760 0.31070 0.35280 1.000 0.0680 calc R H6 H Uiso 0.39390 0.15530 0.43300 1.000 0.0810 calc R H7A H Uiso 0.15270 0.13060 0.27700 1.000 0.1100 calc R H7B H Uiso 0.28240 0.04440 0.32480 1.000 0.1100 calc R H8A H Uiso 0.48000 0.10730 0.20590 1.000 0.1180 calc R H8B H Uiso 0.60560 0.12580 0.29400 1.000 0.1180 calc R H9A H Uiso 0.61630 0.27350 0.21230 1.000 0.1050 calc R H9B H Uiso 0.36500 0.27370 0.20270 1.000 0.1050 calc R H12A H Uiso 0.70860 0.45540 0.22580 1.000 0.1150 calc R H12B H Uiso 0.87410 0.39070 0.27990 1.000 0.1150 calc R H12C H Uiso 0.82130 0.50220 0.30860 1.000 0.1150 calc R H13A H Uiso 0.54650 0.53910 0.39850 1.000 0.0890 calc R H13B H Uiso 0.65720 0.45930 0.45970 1.000 0.0890 calc R H14 H Uiso 0.21250 0.48320 0.43010 1.000 0.0760 calc R H6O H Uiso 0.246(6) -0.040(3) 0.028(3) 1.000 0.1060 . . H17A H Uiso -0.10870 0.18450 0.12270 1.000 0.1310 calc R H17B H Uiso 0.04900 0.08880 0.10950 1.000 0.1310 calc R H18 H Uiso 0.17110 0.10850 -0.08060 1.000 0.0700 calc R H19 H Uiso 0.42480 0.28180 -0.04840 1.000 0.0670 calc R H20 H Uiso 0.09590 0.24430 -0.17140 1.000 0.0830 calc R H21A H Uiso 0.33520 0.42630 -0.16520 1.000 0.1010 calc R H21B H Uiso 0.13700 0.40610 -0.22730 1.000 0.1010 calc R H22A H Uiso 0.33010 0.27610 -0.29960 1.000 0.1160 calc R H22B H Uiso 0.46100 0.37800 -0.30560 1.000 0.1160 calc R H23A H Uiso 0.68040 0.32820 -0.18960 1.000 0.1060 calc R H23B H Uiso 0.68860 0.24480 -0.26270 1.000 0.1060 calc R H26A H Uiso 0.90290 0.10400 -0.20790 1.000 0.1040 calc R H26B H Uiso 0.71460 0.05830 -0.26410 1.000 0.1040 calc R H26C H Uiso 0.81640 -0.00520 -0.18760 1.000 0.1040 calc R H27A H Uiso 0.68910 0.01230 -0.04270 1.000 0.0880 calc R H27B H Uiso 0.48170 -0.02130 -0.09330 1.000 0.0880 calc R H28 H Uiso 0.51430 0.12630 0.03640 1.000 0.0800 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C6 122.1(3) . . . yes C14 O3 H3O 99(3) . . . no C15 O4 C20 120.0(3) . . . yes C28 O6 H6O 111(3) . . . no O1 C1 C2 120.3(4) . . . yes O1 C1 O2 117.4(4) . . . yes O2 C1 C2 122.3(4) . . . yes C1 C2 C3 115.3(4) . . . no C1 C2 C4 117.6(3) . . . no C3 C2 C4 127.0(4) . . . no C5 C4 C14 109.5(2) . . . no C2 C4 C14 116.3(3) . . . no C2 C4 C5 108.3(3) . . . no C4 C5 C10 115.6(3) . . . no C6 C5 C10 112.0(3) . . . no C4 C5 C6 107.2(2) . . . no O1 C6 C5 109.6(3) . . . yes C5 C6 C7 113.5(3) . . . no O1 C6 C7 107.0(3) . . . yes C6 C7 C8 110.0(3) . . . no C7 C8 C9 110.9(4) . . . no C8 C9 C10 113.3(4) . . . no C9 C10 C11 125.6(4) . . . no C5 C10 C11 120.8(3) . . . no C5 C10 C9 113.4(3) . . . no C12 C11 C13 112.7(3) . . . no C10 C11 C13 122.7(4) . . . no C10 C11 C12 124.5(4) . . . no C11 C13 C14 115.5(3) . . . no C4 C14 C13 110.9(3) . . . no O3 C14 C13 108.8(3) . . . yes O3 C14 C4 110.7(3) . . . yes C2 C3 H3B 120.00 . . . no H3A C3 H3B 120.00 . . . no C2 C3 H3A 120.00 . . . no C14 C4 H4 107.00 . . . no C5 C4 H4 107.00 . . . no C2 C4 H4 107.00 . . . no C4 C5 H5 107.00 . . . no C10 C5 H5 107.00 . . . no C6 C5 H5 107.00 . . . no C7 C6 H6 109.00 . . . no C5 C6 H6 109.00 . . . no O1 C6 H6 109.00 . . . no C6 C7 H7B 110.00 . . . no C8 C7 H7B 110.00 . . . no H7A C7 H7B 108.00 . . . no C8 C7 H7A 110.00 . . . no C6 C7 H7A 110.00 . . . no C7 C8 H8B 109.00 . . . no C9 C8 H8B 110.00 . . . no H8A C8 H8B 108.00 . . . no C9 C8 H8A 109.00 . . . no C7 C8 H8A 109.00 . . . no C8 C9 H9A 109.00 . . . no C10 C9 H9B 109.00 . . . no C8 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no C10 C9 H9A 109.00 . . . no C11 C12 H12B 109.00 . . . no H12A C12 H12B 109.00 . . . no H12A C12 H12C 109.00 . . . no C11 C12 H12C 109.00 . . . no H12B C12 H12C 110.00 . . . no C11 C12 H12A 110.00 . . . no C14 C13 H13A 108.00 . . . no C11 C13 H13A 108.00 . . . no H13A C13 H13B 107.00 . . . no C11 C13 H13B 108.00 . . . no C14 C13 H13B 108.00 . . . no C13 C14 H14 109.00 . . . no O3 C14 H14 109.00 . . . no C4 C14 H14 109.00 . . . no O4 C15 C16 120.0(4) . . . yes O5 C15 C16 124.7(4) . . . yes O4 C15 O5 115.4(4) . . . yes C15 C16 C18 119.6(4) . . . no C17 C16 C18 126.3(4) . . . no C15 C16 C17 114.0(4) . . . no C16 C18 C28 118.1(3) . . . no C19 C18 C28 110.1(3) . . . no C16 C18 C19 108.9(3) . . . no C18 C19 C20 108.1(3) . . . no C20 C19 C24 111.9(3) . . . no C18 C19 C24 112.5(3) . . . no O4 C20 C19 110.2(3) . . . yes C19 C20 C21 115.3(3) . . . no O4 C20 C21 106.1(3) . . . yes C20 C21 C22 108.2(3) . . . no C21 C22 C23 109.7(4) . . . no C22 C23 C24 113.0(3) . . . no C19 C24 C25 121.8(3) . . . no C23 C24 C25 125.2(3) . . . no C19 C24 C23 112.7(3) . . . no C24 C25 C27 122.0(3) . . . no C26 C25 C27 114.0(3) . . . no C24 C25 C26 124.0(3) . . . no C25 C27 C28 116.0(3) . . . no O6 C28 C27 110.8(3) . . . yes C18 C28 C27 110.2(3) . . . no O6 C28 C18 115.5(3) . . . yes C16 C17 H17A 120.00 . . . no C16 C17 H17B 120.00 . . . no H17A C17 H17B 120.00 . . . no C16 C18 H18 106.00 . . . no C19 C18 H18 106.00 . . . no C28 C18 H18 106.00 . . . no C18 C19 H19 108.00 . . . no C20 C19 H19 108.00 . . . no C24 C19 H19 108.00 . . . no O4 C20 H20 108.00 . . . no C19 C20 H20 108.00 . . . no C21 C20 H20 108.00 . . . no C20 C21 H21A 110.00 . . . no C20 C21 H21B 110.00 . . . no C22 C21 H21A 110.00 . . . no C22 C21 H21B 110.00 . . . no H21A C21 H21B 108.00 . . . no C21 C22 H22A 110.00 . . . no C21 C22 H22B 110.00 . . . no C23 C22 H22A 110.00 . . . no C23 C22 H22B 110.00 . . . no H22A C22 H22B 108.00 . . . no C22 C23 H23A 109.00 . . . no C22 C23 H23B 109.00 . . . no C24 C23 H23A 109.00 . . . no C24 C23 H23B 109.00 . . . no H23A C23 H23B 108.00 . . . no C25 C26 H26A 109.00 . . . no C25 C26 H26B 109.00 . . . no C25 C26 H26C 110.00 . . . no H26A C26 H26B 109.00 . . . no H26A C26 H26C 109.00 . . . no H26B C26 H26C 110.00 . . . no C25 C27 H27A 108.00 . . . no C25 C27 H27B 108.00 . . . no C28 C27 H27A 108.00 . . . no C28 C27 H27B 108.00 . . . no H27A C27 H27B 107.00 . . . no O6 C28 H28 107.00 . . . no C18 C28 H28 107.00 . . . no C27 C28 H28 107.00 . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.334(6) . . yes O1 C6 1.445(5) . . yes O2 C1 1.213(6) . . yes O3 C14 1.431(4) . . yes O3 H3O 0.77(4) . . no O4 C15 1.344(5) . . yes O4 C20 1.472(4) . . yes O5 C15 1.212(6) . . yes O6 C28 1.414(5) . . yes O6 H6O 0.98(4) . . no C1 C2 1.499(6) . . no C2 C3 1.296(5) . . no C2 C4 1.492(5) . . no C4 C14 1.508(5) . . no C4 C5 1.526(4) . . no C5 C10 1.512(5) . . no C5 C6 1.530(4) . . no C6 C7 1.503(5) . . no C7 C8 1.504(7) . . no C8 C9 1.511(6) . . no C9 C10 1.504(6) . . no C10 C11 1.320(5) . . no C11 C13 1.490(6) . . no C11 C12 1.512(6) . . no C13 C14 1.524(5) . . no C3 H3B 0.9300 . . no C3 H3A 0.9300 . . no C4 H4 0.9800 . . no C5 H5 0.9800 . . no C6 H6 0.9800 . . no C7 H7A 0.9700 . . no C7 H7B 0.9700 . . no C8 H8B 0.9700 . . no C8 H8A 0.9700 . . no C9 H9A 0.9700 . . no C9 H9B 0.9700 . . no C12 H12A 0.9600 . . no C12 H12B 0.9600 . . no C12 H12C 0.9600 . . no C13 H13B 0.9700 . . no C13 H13A 0.9700 . . no C14 H14 0.9800 . . no C15 C16 1.485(6) . . no C16 C18 1.514(5) . . no C16 C17 1.306(6) . . no C18 C19 1.528(5) . . no C18 C28 1.506(5) . . no C19 C24 1.522(5) . . no C19 C20 1.501(5) . . no C20 C21 1.501(6) . . no C21 C22 1.530(6) . . no C22 C23 1.513(6) . . no C23 C24 1.526(6) . . no C24 C25 1.321(5) . . no C25 C27 1.499(6) . . no C25 C26 1.511(5) . . no C27 C28 1.504(5) . . no C17 H17A 0.9300 . . no C17 H17B 0.9300 . . no C18 H18 0.9800 . . no C19 H19 0.9800 . . no C20 H20 0.9800 . . no C21 H21A 0.9700 . . no C21 H21B 0.9700 . . no C22 H22A 0.9700 . . no C22 H22B 0.9700 . . no C23 H23A 0.9700 . . no C23 H23B 0.9700 . . no C26 H26A 0.9600 . . no C26 H26B 0.9600 . . no C26 H26C 0.9600 . . no C27 H27A 0.9700 . . no C27 H27B 0.9700 . . no C28 H28 0.9800 . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 C14 3.187(5) . 2_546 no O2 O3 2.841(4) . 2_546 no O3 C3 2.897(5) . . no O3 O2 2.841(4) . 2_556 no O4 O6 3.212(4) . 2_555 no O5 O6 3.003(5) . 2_555 no O6 O5 3.003(5) . 2_545 no O6 O4 3.212(4) . 2_545 no O6 C17 2.913(6) . . no O1 H3O 2.81(4) . 2_546 no O2 H14 2.7400 . 2_546 no O2 H3B 2.3600 . . no O2 H3O 2.11(4) . 2_546 no O3 H22B 2.8300 . 1_556 no O3 H3A 2.2500 . . no O3 H6 2.6700 . 2_656 no O4 H6O 2.45(4) . 2_555 no O4 H23A 2.8400 . 1_455 no O5 H27B 2.8900 . 2_555 no O5 H6O 2.06(4) . 2_555 no O5 H17A 2.3700 . . no O6 H8A 2.7400 . . no O6 H17B 2.2600 . . no O6 H21A 2.7800 . 2_645 no C3 O3 2.897(5) . . no C12 C26 3.476(6) . 2_755 no C14 O2 3.187(5) . 2_556 no C17 O6 2.913(6) . . no C26 C12 3.476(6) . 2_745 no C1 H3O 2.84(4) . 2_546 no C1 H5 2.7500 . . no C3 H14 3.0700 . . no C3 H13B 2.8600 . 1_455 no C9 H12A 2.9800 . . no C9 H12B 3.0500 . . no C11 H4 3.0400 . . no C11 H26B 2.9900 . 2_655 no C12 H26C 3.0800 . 2_755 no C12 H9A 2.6300 . . no C13 H26B 3.0600 . 2_655 no C14 H3A 2.7200 . . no C15 H6O 2.64(4) . 2_555 no C15 H19 2.8300 . . no C16 H20 3.0300 . . no C17 H7A 3.0000 . . no C23 H26A 2.9700 . . no C23 H26B 3.0500 . . no C24 H28 3.0300 . . no C25 H12A 3.0900 . 2_645 no C25 H18 2.9200 . . no C26 H23B 2.6200 . . no C26 H12C 3.0500 . 2_745 no C27 H12A 3.0900 . 2_645 no C28 H17B 2.8400 . . no H3A O3 2.2500 . . no H3A C14 2.7200 . . no H3B O2 2.3600 . . no H3O H6 2.2500 . 2_656 no H3O H13A 2.5000 . . no H3O O1 2.81(4) . 2_556 no H3O O2 2.11(4) . 2_556 no H3O C1 2.84(4) . 2_556 no H4 H6 2.3200 . . no H4 C11 3.0400 . . no H5 H14 2.5900 . . no H5 H12B 2.2800 . 1_455 no H5 C1 2.7500 . . no H6 H4 2.3200 . . no H6 H8B 2.5300 . . no H6 O3 2.6700 . 2_646 no H6 H3O 2.2500 . 2_646 no H6O H27B 2.3800 . . no H6O O4 2.45(4) . 2_545 no H6O H17B 2.4400 . . no H6O C15 2.64(4) . 2_545 no H6O O5 2.06(4) . 2_545 no H7A H9B 2.5700 . . no H7A C17 3.0000 . . no H8A O6 2.7400 . . no H8B H6 2.5300 . . no H9A C12 2.6300 . . no H9A H17A 2.4900 . 1_655 no H9A H12A 2.4700 . . no H9A H12B 2.4500 . . no H9B H7A 2.5700 . . no H12A C25 3.0900 . 2_655 no H12A C9 2.9800 . . no H12A H9A 2.4700 . . no H12A H27B 2.3600 . 2_655 no H12A C27 3.0900 . 2_655 no H12B H5 2.2800 . 1_655 no H12B H9A 2.4500 . . no H12B C9 3.0500 . . no H12C C26 3.0500 . 2_755 no H12C H13A 2.2500 . . no H12C H13B 2.5900 . . no H13A H12C 2.2500 . . no H13A H3O 2.5000 . . no H13B H12C 2.5900 . . no H13B C3 2.8600 . 1_655 no H14 O2 2.7400 . 2_556 no H14 C3 3.0700 . . no H14 H5 2.5900 . . no H17A O5 2.3700 . . no H17A H9A 2.4900 . 1_455 no H17B O6 2.2600 . . no H17B C28 2.8400 . . no H17B H6O 2.4400 . . no H18 C25 2.9200 . . no H18 H20 2.3100 . . no H18 H26A 2.5500 . 1_455 no H18 H27B 2.5900 . . no H19 C15 2.8300 . . no H19 H28 2.4900 . . no H20 C16 3.0300 . . no H20 H18 2.3100 . . no H20 H22A 2.4800 . . no H20 H26A 2.2700 . 1_455 no H21A H23A 2.5300 . . no H21A O6 2.7800 . 2_655 no H22A H20 2.4800 . . no H22B O3 2.8300 . 1_554 no H23A O4 2.8400 . 1_655 no H23A H21A 2.5300 . . no H23B C26 2.6200 . . no H23B H26A 2.4300 . . no H23B H26B 2.4600 . . no H26A C23 2.9700 . . no H26A H18 2.5500 . 1_655 no H26A H20 2.2700 . 1_655 no H26A H23B 2.4300 . . no H26B C23 3.0500 . . no H26B H23B 2.4600 . . no H26B C11 2.9900 . 2_645 no H26B C13 3.0600 . 2_645 no H26C H27A 2.3600 . . no H26C H27B 2.5400 . . no H26C C12 3.0800 . 2_745 no H27A H26C 2.3600 . . no H27B H6O 2.3800 . . no H27B H18 2.5900 . . no H27B H26C 2.5400 . . no H27B O5 2.8900 . 2_545 no H27B H12A 2.3600 . 2_645 no H28 C24 3.0300 . . no H28 H19 2.4900 . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O3 H3O O2 0.77(4) 2.11(4) 2.841(4) 159(5) 2_556 yes O6 H6O O4 0.98(4) 2.45(4) 3.212(4) 134(4) 2_545 yes O6 H6O O5 0.98(4) 2.06(4) 3.003(5) 161(3) 2_545 yes C3 H3A O3 0.9300 2.2500 2.897(5) 126.00 . yes C3 H3B O2 0.9300 2.3600 2.706(5) 102.00 . yes C17 H17A O5 0.9300 2.3700 2.717(6) 102.00 . yes C17 H17B O6 0.9300 2.2600 2.913(6) 127.00 . 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O1 C1 O2 176.6(4) . . . . no C6 O1 C1 C2 -1.7(6) . . . . no C1 O1 C6 C7 -154.3(4) . . . . no C1 O1 C6 C5 -30.8(5) . . . . no C15 O4 C20 C21 -163.0(3) . . . . no C15 O4 C20 C19 -37.6(4) . . . . no C20 O4 C15 C16 2.3(5) . . . . no C20 O4 C15 O5 -177.1(4) . . . . no O1 C1 C2 C3 -179.6(4) . . . . no O2 C1 C2 C3 2.2(7) . . . . no O1 C1 C2 C4 1.4(6) . . . . no O2 C1 C2 C4 -176.7(4) . . . . no C3 C2 C4 C5 -147.8(4) . . . . no C3 C2 C4 C14 -24.0(5) . . . . no C1 C2 C4 C14 154.8(3) . . . . no C1 C2 C4 C5 31.0(4) . . . . no C2 C4 C14 O3 59.3(4) . . . . no C5 C4 C14 C13 -56.7(3) . . . . no C14 C4 C5 C6 170.4(3) . . . . no C2 C4 C5 C6 -61.9(3) . . . . no C14 C4 C5 C10 44.8(4) . . . . no C2 C4 C14 C13 -179.8(3) . . . . no C5 C4 C14 O3 -177.6(3) . . . . no C2 C4 C5 C10 172.6(3) . . . . no C4 C5 C6 O1 62.6(3) . . . . no C6 C5 C10 C9 45.9(4) . . . . no C4 C5 C6 C7 -177.8(3) . . . . no C10 C5 C6 O1 -169.7(3) . . . . no C6 C5 C10 C11 -139.3(4) . . . . no C10 C5 C6 C7 -50.1(4) . . . . no C4 C5 C10 C9 169.0(3) . . . . no C4 C5 C10 C11 -16.2(5) . . . . no C5 C6 C7 C8 56.0(4) . . . . no O1 C6 C7 C8 177.1(3) . . . . no C6 C7 C8 C9 -57.6(5) . . . . no C7 C8 C9 C10 55.2(5) . . . . no C8 C9 C10 C11 136.0(4) . . . . no C8 C9 C10 C5 -49.5(5) . . . . no C5 C10 C11 C12 -177.5(3) . . . . no C9 C10 C11 C13 173.4(4) . . . . no C9 C10 C11 C12 -3.4(7) . . . . no C5 C10 C11 C13 -0.7(6) . . . . no C10 C11 C13 C14 -12.5(6) . . . . no C12 C11 C13 C14 164.6(3) . . . . no C11 C13 C14 C4 41.9(4) . . . . no C11 C13 C14 O3 163.8(3) . . . . no O4 C15 C16 C18 5.1(6) . . . . no O4 C15 C16 C17 -171.5(4) . . . . no O5 C15 C16 C18 -175.6(4) . . . . no O5 C15 C16 C17 7.8(6) . . . . no C15 C16 C18 C28 149.1(4) . . . . no C15 C16 C18 C19 22.7(4) . . . . no C17 C16 C18 C19 -161.2(4) . . . . no C17 C16 C18 C28 -34.8(6) . . . . no C16 C18 C19 C20 -56.1(3) . . . . no C28 C18 C19 C24 49.0(4) . . . . no C16 C18 C28 O6 47.9(4) . . . . no C16 C18 C28 C27 174.5(3) . . . . no C19 C18 C28 O6 173.7(3) . . . . no C19 C18 C28 C27 -59.7(4) . . . . no C16 C18 C19 C24 179.9(3) . . . . no C28 C18 C19 C20 173.0(3) . . . . no C18 C19 C20 O4 64.8(4) . . . . no C24 C19 C20 C21 -50.8(4) . . . . no C18 C19 C24 C23 166.8(3) . . . . no C18 C19 C24 C25 -18.4(4) . . . . no C20 C19 C24 C23 44.9(4) . . . . no C20 C19 C24 C25 -140.3(3) . . . . no C18 C19 C20 C21 -175.1(3) . . . . no C24 C19 C20 O4 -170.8(3) . . . . no O4 C20 C21 C22 180.0(3) . . . . no C19 C20 C21 C22 57.8(4) . . . . no C20 C21 C22 C23 -59.2(4) . . . . no C21 C22 C23 C24 57.4(5) . . . . no C22 C23 C24 C19 -50.1(4) . . . . no C22 C23 C24 C25 135.4(4) . . . . no C19 C24 C25 C26 176.5(3) . . . . no C19 C24 C25 C27 -2.0(5) . . . . no C23 C24 C25 C26 -9.4(6) . . . . no C23 C24 C25 C27 172.2(3) . . . . no C24 C25 C27 C28 -9.2(5) . . . . no C26 C25 C27 C28 172.2(3) . . . . no C25 C27 C28 O6 169.3(3) . . . . no C25 C27 C28 C18 40.1(4) . . . . no