# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'K Nicolaou' _publ_contact_author_email KCN@SCRIPPS.EDU _publ_section_title ; Synthesis of Functionalized Maoecrystal V Core Structures ; loop_ _publ_author_name 'K Nicolaou' 'David C.-K. Chen' 'Lujiang Deng.' 'Dong Lin.' 'Adam C. Talbot' # Attachment 'compound 3.cif' data_shelxs _database_code_depnum_ccdc_archive 'CCDC 742693' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H22 O7' _chemical_formula_sum 'C19 H22 O7' _chemical_formula_weight 362.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.838(3) _cell_length_b 7.0826(14) _cell_length_c 17.443(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.23(3) _cell_angle_gamma 90.00 _cell_volume 1623.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4298 _cell_measurement_theta_min 2.4590 _cell_measurement_theta_max 30.9245 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9755 _exptl_absorpt_process_details 'Blessing, R.H. (1995) Acta Cryst A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11807 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4007 _reflns_number_gt 3836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0676P)^2^+0.5779P] 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_number_reflns 4007 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.001 _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 O4 O 0.29511(6) -0.01133(12) 0.41641(5) 0.01813(19) Uani 1 1 d . . . O2 O 0.46491(7) -0.01095(13) 0.33335(5) 0.0205(2) Uani 1 1 d . . . O1 O 0.43636(6) 0.25266(13) 0.40481(5) 0.0193(2) Uani 1 1 d . . . O5 O 0.09386(7) -0.09040(13) 0.29306(6) 0.0220(2) Uani 1 1 d . . . O3 O 0.14314(8) 0.49217(14) 0.25096(7) 0.0305(2) Uani 1 1 d . . . O6 O 0.08406(7) -0.23673(13) 0.40154(6) 0.0258(2) Uani 1 1 d . . . O7 O 0.24781(8) 0.49435(15) 0.57919(6) 0.0315(2) Uani 1 1 d . . . C1 C 0.06254(9) 0.28259(17) 0.38338(7) 0.0181(2) Uani 1 1 d . . . H1A H 0.0146 0.2072 0.3402 0.022 Uiso 1 1 calc R . . H1B H 0.0498 0.4181 0.3701 0.022 Uiso 1 1 calc R . . C2 C 0.17293(8) 0.23190(16) 0.38997(7) 0.0153(2) Uani 1 1 d . . . C3 C 0.19789(8) 0.03372(17) 0.42589(7) 0.0160(2) Uani 1 1 d . . . C4 C 0.20008(9) 0.19590(17) 0.31136(7) 0.0166(2) Uani 1 1 d . . . C5 C 0.29347(9) 0.05859(17) 0.33852(7) 0.0167(2) Uani 1 1 d . . . H5 H 0.2769 -0.0514 0.3007 0.020 Uiso 1 1 calc R . . C6 C 0.11333(9) 0.08086(18) 0.25422(7) 0.0199(2) Uani 1 1 d . . . H6A H 0.0508 0.1587 0.2372 0.024 Uiso 1 1 calc R . . H6B H 0.1313 0.0469 0.2053 0.024 Uiso 1 1 calc R . . C7 C 0.30835(9) 0.40691(18) 0.24815(7) 0.0199(3) Uani 1 1 d . . . C8 C 0.21673(9) 0.37544(19) 0.52700(8) 0.0216(3) Uani 1 1 d . . . C9 C 0.20268(9) 0.02983(18) 0.51451(7) 0.0200(2) Uani 1 1 d . . . H9A H 0.2744 0.0260 0.5495 0.024 Uiso 1 1 calc R . . H9B H 0.1677 -0.0840 0.5255 0.024 Uiso 1 1 calc R . . C10 C 0.21207(9) 0.37734(18) 0.26817(7) 0.0199(2) Uani 1 1 d . . . C11 C 0.53391(10) 0.3341(2) 0.41300(8) 0.0246(3) Uani 1 1 d . . . H11A H 0.5843 0.2333 0.4194 0.037 Uiso 1 1 calc R . . H11B H 0.5540 0.4164 0.4605 0.037 Uiso 1 1 calc R . . H11C H 0.5300 0.4083 0.3647 0.037 Uiso 1 1 calc R . . C12 C 0.04681(9) 0.23903(19) 0.46578(8) 0.0220(3) Uani 1 1 d . . . H12A H 0.0098 0.3448 0.4810 0.026 Uiso 1 1 calc R . . H12B H 0.0050 0.1236 0.4609 0.026 Uiso 1 1 calc R . . C13 C 0.24183(9) 0.37595(17) 0.44827(7) 0.0186(2) Uani 1 1 d . . . H13A H 0.3142 0.3419 0.4586 0.022 Uiso 1 1 calc R . . H13B H 0.2306 0.5036 0.4240 0.022 Uiso 1 1 calc R . . C14 C 0.37773(10) 0.23938(19) 0.25631(8) 0.0207(3) Uani 1 1 d . . . H14A H 0.4437 0.2824 0.2515 0.025 Uiso 1 1 calc R . . H14B H 0.3473 0.1502 0.2115 0.025 Uiso 1 1 calc R . . C15 C 0.11940(9) -0.10767(17) 0.37383(8) 0.0186(2) Uani 1 1 d . . . C16 C 0.49249(10) -0.1401(2) 0.39974(8) 0.0253(3) Uani 1 1 d . . . H16A H 0.5196 -0.0697 0.4503 0.038 Uiso 1 1 calc R . . H16B H 0.5445 -0.2274 0.3935 0.038 Uiso 1 1 calc R . . H16C H 0.4323 -0.2116 0.4008 0.038 Uiso 1 1 calc R . . C17 C 0.15003(10) 0.21005(19) 0.53236(8) 0.0217(3) Uani 1 1 d . . . H17 H 0.1409 0.2031 0.5869 0.026 Uiso 1 1 calc R . . C18 C 0.32636(11) 0.5766(2) 0.22229(9) 0.0274(3) Uani 1 1 d . . . H18A H 0.2784 0.6757 0.2169 0.033 Uiso 1 1 calc R . . H18B H 0.3871 0.5984 0.2092 0.033 Uiso 1 1 calc R . . C19 C 0.39664(9) 0.13595(17) 0.33687(7) 0.0180(2) 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 O4 0.0144(4) 0.0219(4) 0.0187(4) 0.0036(3) 0.0061(3) 0.0029(3) O2 0.0182(4) 0.0236(5) 0.0211(4) 0.0006(3) 0.0081(3) 0.0046(3) O1 0.0145(4) 0.0239(4) 0.0193(4) -0.0036(3) 0.0051(3) -0.0026(3) O5 0.0222(4) 0.0202(4) 0.0213(5) -0.0015(3) 0.0034(3) -0.0044(3) O3 0.0256(5) 0.0286(5) 0.0393(6) 0.0137(4) 0.0132(4) 0.0087(4) O6 0.0270(5) 0.0200(4) 0.0312(5) 0.0011(4) 0.0100(4) -0.0048(4) O7 0.0358(6) 0.0330(6) 0.0235(5) -0.0091(4) 0.0062(4) -0.0041(4) C1 0.0144(5) 0.0191(5) 0.0205(6) 0.0011(4) 0.0049(4) 0.0010(4) C2 0.0131(5) 0.0163(5) 0.0159(5) 0.0001(4) 0.0038(4) -0.0002(4) C3 0.0129(5) 0.0171(5) 0.0181(5) 0.0002(4) 0.0051(4) 0.0008(4) C4 0.0140(5) 0.0191(5) 0.0162(5) 0.0006(4) 0.0041(4) 0.0003(4) C5 0.0154(5) 0.0183(5) 0.0158(5) 0.0008(4) 0.0041(4) 0.0004(4) C6 0.0184(5) 0.0214(6) 0.0174(6) 0.0002(4) 0.0021(4) -0.0018(4) C7 0.0196(5) 0.0239(6) 0.0161(5) -0.0002(4) 0.0055(4) -0.0008(5) C8 0.0188(6) 0.0241(6) 0.0201(6) -0.0015(5) 0.0035(4) 0.0017(5) C9 0.0199(5) 0.0227(6) 0.0176(6) 0.0033(5) 0.0064(4) 0.0011(4) C10 0.0201(6) 0.0221(6) 0.0167(5) 0.0014(5) 0.0046(4) 0.0001(4) C11 0.0171(6) 0.0284(7) 0.0285(7) -0.0041(5) 0.0076(5) -0.0056(5) C12 0.0180(6) 0.0251(6) 0.0247(6) 0.0013(5) 0.0092(5) 0.0018(5) C13 0.0166(5) 0.0180(5) 0.0201(6) -0.0021(4) 0.0041(4) -0.0018(4) C14 0.0203(6) 0.0253(6) 0.0179(6) 0.0018(5) 0.0083(5) 0.0020(5) C15 0.0160(5) 0.0171(5) 0.0219(6) -0.0008(4) 0.0047(4) 0.0009(4) C16 0.0249(6) 0.0265(6) 0.0254(6) 0.0048(5) 0.0093(5) 0.0086(5) C17 0.0231(6) 0.0247(6) 0.0190(6) 0.0002(5) 0.0089(5) 0.0018(5) C18 0.0276(7) 0.0257(7) 0.0310(7) 0.0017(5) 0.0123(5) -0.0022(5) C19 0.0159(5) 0.0200(6) 0.0181(5) -0.0009(4) 0.0055(4) 0.0010(4) _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 O4 C5 1.4396(14) . ? O4 C3 1.4417(14) . ? O2 C19 1.4196(14) . ? O2 C16 1.4306(16) . ? O1 C19 1.4078(15) . ? O1 C11 1.4333(15) . ? O5 C15 1.3466(16) . ? O5 C6 1.4550(16) . ? O3 C10 1.2175(16) . ? O6 C15 1.2067(16) . ? O7 C8 1.2158(17) . ? C1 C2 1.5381(16) . ? C1 C12 1.5506(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5319(16) . ? C2 C13 1.5419(16) . ? C2 C4 1.5519(16) . ? C3 C9 1.5265(17) . ? C3 C15 1.5459(17) . ? C4 C10 1.5248(17) . ? C4 C6 1.5329(17) . ? C4 C5 1.5675(16) . ? C5 C19 1.5378(16) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C18 1.3345(19) . ? C7 C10 1.4939(17) . ? C7 C14 1.5048(18) . ? C8 C17 1.5122(18) . ? C8 C13 1.5181(17) . ? C9 C17 1.5488(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.5469(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.5329(17) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17 1.0000 . ? C18 H18A 0.9500 . ? C18 H18B 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 C5 O4 C3 107.00(9) . . ? C19 O2 C16 116.49(9) . . ? C19 O1 C11 115.33(10) . . ? C15 O5 C6 122.46(10) . . ? C2 C1 C12 107.97(10) . . ? C2 C1 H1A 110.1 . . ? C12 C1 H1A 110.1 . . ? C2 C1 H1B 110.1 . . ? C12 C1 H1B 110.1 . . ? H1A C1 H1B 108.4 . . ? C3 C2 C1 109.63(9) . . ? C3 C2 C13 108.83(10) . . ? C1 C2 C13 106.83(10) . . ? C3 C2 C4 97.17(9) . . ? C1 C2 C4 118.80(10) . . ? C13 C2 C4 114.88(10) . . ? O4 C3 C9 111.45(10) . . ? O4 C3 C2 104.77(9) . . ? C9 C3 C2 111.31(10) . . ? O4 C3 C15 107.38(9) . . ? C9 C3 C15 112.52(10) . . ? C2 C3 C15 109.04(10) . . ? C10 C4 C6 108.11(10) . . ? C10 C4 C2 113.07(10) . . ? C6 C4 C2 107.76(9) . . ? C10 C4 C5 117.73(10) . . ? C6 C4 C5 105.70(10) . . ? C2 C4 C5 103.86(9) . . ? O4 C5 C19 113.55(10) . . ? O4 C5 C4 105.47(9) . . ? C19 C5 C4 117.11(10) . . ? O4 C5 H5 106.7 . . ? C19 C5 H5 106.7 . . ? C4 C5 H5 106.7 . . ? O5 C6 C4 111.21(10) . . ? O5 C6 H6A 109.4 . . ? C4 C6 H6A 109.4 . . ? O5 C6 H6B 109.4 . . ? C4 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C18 C7 C10 118.67(12) . . ? C18 C7 C14 124.13(12) . . ? C10 C7 C14 117.17(11) . . ? O7 C8 C17 124.75(12) . . ? O7 C8 C13 123.25(12) . . ? C17 C8 C13 112.00(11) . . ? C3 C9 C17 108.33(10) . . ? C3 C9 H9A 110.0 . . ? C17 C9 H9A 110.0 . . ? C3 C9 H9B 110.0 . . ? C17 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? O3 C10 C7 122.41(12) . . ? O3 C10 C4 119.13(11) . . ? C7 C10 C4 118.46(10) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C1 110.97(10) . . ? C17 C12 H12A 109.4 . . ? C1 C12 H12A 109.4 . . ? C17 C12 H12B 109.4 . . ? C1 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C8 C13 C2 109.01(10) . . ? C8 C13 H13A 109.9 . . ? C2 C13 H13A 109.9 . . ? C8 C13 H13B 109.9 . . ? C2 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C7 C14 C19 112.60(10) . . ? C7 C14 H14A 109.1 . . ? C19 C14 H14A 109.1 . . ? C7 C14 H14B 109.1 . . ? C19 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? O6 C15 O5 118.77(11) . . ? O6 C15 C3 123.63(11) . . ? O5 C15 C3 117.51(10) . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C17 C12 106.79(11) . . ? C8 C17 C9 106.94(10) . . ? C12 C17 C9 109.90(10) . . ? C8 C17 H17 111.0 . . ? C12 C17 H17 111.0 . . ? C9 C17 H17 111.0 . . ? C7 C18 H18A 120.0 . . ? C7 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? O1 C19 O2 112.14(10) . . ? O1 C19 C14 113.62(10) . . ? O2 C19 C14 103.63(10) . . ? O1 C19 C5 108.29(10) . . ? O2 C19 C5 111.96(10) . . ? C14 C19 C5 107.11(10) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.384 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.075 # Attachment 'CCDC_742701.cif.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 742701' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 O5' _chemical_formula_sum 'C17 H18 O5' _chemical_formula_weight 302.31 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9635(14) _cell_length_b 8.8693(18) _cell_length_c 12.590(3) _cell_angle_alpha 98.55(3) _cell_angle_beta 101.29(3) _cell_angle_gamma 105.65(3) _cell_volume 717.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2398 _cell_measurement_theta_min 2.4411 _cell_measurement_theta_max 31.0133 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9797 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details 'Blessing, R.H. (1995) Acta Cryst A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10361 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3522 _reflns_number_gt 2878 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0950P)^2^+0.2246P] 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_number_reflns 3522 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0943 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.2020 _refine_ls_wR_factor_gt 0.1840 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _refine_ls_shift/su_max 0.000 _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 O5 O 1.0878(2) 0.85238(19) 0.57991(13) 0.0301(4) Uani 1 1 d . . . O1 O 0.9669(2) 0.79886(18) 0.92265(12) 0.0282(4) Uani 1 1 d . . . O4 O 0.8707(3) 0.38628(19) 0.80683(14) 0.0322(4) Uani 1 1 d . . . O2 O 0.5050(3) 0.31020(19) 0.58627(14) 0.0344(4) Uani 1 1 d . . . O3 O 1.1586(3) 0.5760(2) 0.90982(15) 0.0382(4) Uani 1 1 d . . . C1 C 1.0436(3) 0.8347(2) 0.75648(18) 0.0240(5) Uani 1 1 d . . . C2 C 1.1586(3) 0.9125(3) 0.69118(18) 0.0248(5) Uani 1 1 d . . . C3 C 0.9837(4) 0.5369(3) 0.85756(18) 0.0274(5) Uani 1 1 d . . . C4 C 0.8401(3) 0.7056(2) 0.72878(18) 0.0241(5) Uani 1 1 d . . . C5 C 0.5863(4) 0.4416(3) 0.64798(19) 0.0280(5) Uani 1 1 d . . . C6 C 1.3353(3) 1.0417(3) 0.74280(19) 0.0286(5) Uani 1 1 d . . . H6 H 1.4174 1.0958 0.6997 0.034 Uiso 1 1 calc R . . C7 C 0.7804(3) 0.5594(3) 0.63489(18) 0.0268(5) Uani 1 1 d . . . H7A H 0.8927 0.5101 0.6391 0.032 Uiso 1 1 calc R . . H7B H 0.7539 0.5903 0.5623 0.032 Uiso 1 1 calc R . . C8 C 1.2751(4) 1.0158(3) 0.9247(2) 0.0294(5) Uani 1 1 d . . . H8 H 1.3128 1.0506 1.0031 0.035 Uiso 1 1 calc R . . C9 C 1.1027(3) 0.8878(3) 0.87067(19) 0.0263(5) Uani 1 1 d . . . C10 C 0.6657(3) 0.7849(3) 0.7112(2) 0.0287(5) Uani 1 1 d . . . H10A H 0.6894 0.8710 0.7766 0.034 Uiso 1 1 calc R . . H10B H 0.6678 0.8339 0.6455 0.034 Uiso 1 1 calc R . . C11 C 0.8531(3) 0.6518(3) 0.84186(18) 0.0247(5) Uani 1 1 d . . . C12 C 1.3905(4) 1.0908(3) 0.8581(2) 0.0315(5) Uani 1 1 d . . . H12 H 1.5111 1.1785 0.8923 0.038 Uiso 1 1 calc R . . C13 C 0.6345(4) 0.5738(3) 0.85224(19) 0.0291(5) Uani 1 1 d . . . H13A H 0.5879 0.6532 0.8958 0.035 Uiso 1 1 calc R . . H13B H 0.6319 0.4840 0.8907 0.035 Uiso 1 1 calc R . . C14 C 0.4531(4) 0.6593(3) 0.6941(2) 0.0330(6) Uani 1 1 d . . . H14A H 0.3688 0.7038 0.7372 0.040 Uiso 1 1 calc R . . H14B H 0.3789 0.6295 0.6147 0.040 Uiso 1 1 calc R . . C15 C 1.2092(4) 0.9222(3) 0.5100(2) 0.0364(6) Uani 1 1 d . . . H15A H 1.2249 1.0370 0.5210 0.055 Uiso 1 1 calc R . . H15B H 1.1408 0.8703 0.4323 0.055 Uiso 1 1 calc R . . H15C H 1.3452 0.9070 0.5288 0.055 Uiso 1 1 calc R . . C16 C 0.4907(4) 0.5113(3) 0.7340(2) 0.0299(5) Uani 1 1 d . . . H16 H 0.3579 0.4328 0.7350 0.036 Uiso 1 1 calc R . . C17 C 0.9691(4) 0.2630(3) 0.8201(2) 0.0350(6) Uani 1 1 d . . . H17A H 1.0943 0.2877 0.7929 0.052 Uiso 1 1 calc R . . H17B H 0.8744 0.1589 0.7776 0.052 Uiso 1 1 calc R . . H17C H 1.0051 0.2593 0.8987 0.052 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 O5 0.0324(9) 0.0307(9) 0.0289(8) 0.0112(7) 0.0117(7) 0.0071(7) O1 0.0333(9) 0.0257(8) 0.0260(8) 0.0051(6) 0.0105(7) 0.0080(7) O4 0.0375(10) 0.0262(8) 0.0362(9) 0.0096(7) 0.0084(7) 0.0142(7) O2 0.0368(10) 0.0266(9) 0.0361(9) 0.0060(7) 0.0069(8) 0.0057(7) O3 0.0326(10) 0.0371(10) 0.0476(11) 0.0145(8) 0.0068(8) 0.0147(8) C1 0.0246(11) 0.0224(10) 0.0270(11) 0.0063(8) 0.0071(9) 0.0093(9) C2 0.0269(11) 0.0247(10) 0.0288(11) 0.0096(9) 0.0101(9) 0.0131(9) C3 0.0302(13) 0.0311(12) 0.0255(11) 0.0108(9) 0.0114(10) 0.0115(10) C4 0.0232(11) 0.0219(10) 0.0281(11) 0.0073(8) 0.0075(9) 0.0067(9) C5 0.0297(12) 0.0252(11) 0.0305(12) 0.0101(9) 0.0066(10) 0.0091(9) C6 0.0280(12) 0.0249(11) 0.0359(12) 0.0114(9) 0.0105(10) 0.0088(9) C7 0.0283(12) 0.0247(11) 0.0288(11) 0.0087(9) 0.0074(9) 0.0087(9) C8 0.0290(12) 0.0278(11) 0.0311(12) 0.0048(9) 0.0048(10) 0.0112(10) C9 0.0267(11) 0.0251(11) 0.0321(12) 0.0090(9) 0.0112(9) 0.0116(9) C10 0.0285(12) 0.0264(11) 0.0356(12) 0.0108(9) 0.0097(10) 0.0122(10) C11 0.0268(11) 0.0245(10) 0.0253(10) 0.0072(8) 0.0105(9) 0.0079(9) C12 0.0295(13) 0.0244(11) 0.0386(13) 0.0063(10) 0.0049(10) 0.0080(10) C13 0.0311(12) 0.0258(11) 0.0329(12) 0.0067(9) 0.0147(10) 0.0074(9) C14 0.0294(13) 0.0303(12) 0.0458(14) 0.0143(10) 0.0138(11) 0.0132(10) C15 0.0432(15) 0.0356(13) 0.0359(13) 0.0140(11) 0.0205(12) 0.0101(11) C16 0.0257(12) 0.0257(11) 0.0384(13) 0.0072(10) 0.0095(10) 0.0069(9) C17 0.0482(15) 0.0277(12) 0.0394(13) 0.0129(10) 0.0175(12) 0.0210(11) _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 O5 C2 1.362(3) . ? O5 C15 1.430(3) . ? O1 C9 1.392(3) . ? O1 C11 1.448(3) . ? O4 C3 1.339(3) . ? O4 C17 1.451(3) . ? O2 C5 1.219(3) . ? O3 C3 1.194(3) . ? C1 C9 1.386(3) . ? C1 C2 1.386(3) . ? C1 C4 1.501(3) . ? C2 C6 1.398(3) . ? C3 C11 1.547(3) . ? C4 C7 1.521(3) . ? C4 C10 1.557(3) . ? C4 C11 1.561(3) . ? C5 C16 1.518(3) . ? C5 C7 1.524(3) . ? C6 C12 1.396(3) . ? C6 H6 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.381(3) . ? C8 C12 1.390(3) . ? C8 H8 0.9500 . ? C10 C14 1.547(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C13 1.533(3) . ? C12 H12 0.9500 . ? C13 C16 1.548(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C16 1.542(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C2 O5 C15 117.38(19) . . ? C9 O1 C11 105.30(16) . . ? C3 O4 C17 116.61(19) . . ? C9 C1 C2 119.8(2) . . ? C9 C1 C4 107.36(19) . . ? C2 C1 C4 132.5(2) . . ? O5 C2 C1 115.5(2) . . ? O5 C2 C6 125.6(2) . . ? C1 C2 C6 118.8(2) . . ? O3 C3 O4 124.7(2) . . ? O3 C3 C11 125.0(2) . . ? O4 C3 C11 110.28(19) . . ? C1 C4 C7 122.82(18) . . ? C1 C4 C10 108.48(17) . . ? C7 C4 C10 107.46(18) . . ? C1 C4 C11 99.47(17) . . ? C7 C4 C11 109.60(17) . . ? C10 C4 C11 108.15(17) . . ? O2 C5 C16 123.5(2) . . ? O2 C5 C7 122.2(2) . . ? C16 C5 C7 113.76(19) . . ? C12 C6 C2 119.6(2) . . ? C12 C6 H6 120.2 . . ? C2 C6 H6 120.2 . . ? C4 C7 C5 107.07(18) . . ? C4 C7 H7A 110.3 . . ? C5 C7 H7A 110.3 . . ? C4 C7 H7B 110.3 . . ? C5 C7 H7B 110.3 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C12 116.3(2) . . ? C9 C8 H8 121.8 . . ? C12 C8 H8 121.8 . . ? C8 C9 C1 123.1(2) . . ? C8 C9 O1 124.8(2) . . ? C1 C9 O1 112.04(19) . . ? C14 C10 C4 110.63(17) . . ? C14 C10 H10A 109.5 . . ? C4 C10 H10A 109.5 . . ? C14 C10 H10B 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O1 C11 C13 114.76(17) . . ? O1 C11 C3 105.71(18) . . ? C13 C11 C3 110.39(18) . . ? O1 C11 C4 103.43(16) . . ? C13 C11 C4 108.94(19) . . ? C3 C11 C4 113.53(17) . . ? C8 C12 C6 122.3(2) . . ? C8 C12 H12 118.8 . . ? C6 C12 H12 118.8 . . ? C11 C13 C16 108.12(18) . . ? C11 C13 H13A 110.1 . . ? C16 C13 H13A 110.1 . . ? C11 C13 H13B 110.1 . . ? C16 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C16 C14 C10 107.54(19) . . ? C16 C14 H14A 110.2 . . ? C10 C14 H14A 110.2 . . ? C16 C14 H14B 110.2 . . ? C10 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C5 C16 C14 103.47(19) . . ? C5 C16 C13 114.58(19) . . ? C14 C16 C13 106.37(19) . . ? C5 C16 H16 110.7 . . ? C14 C16 H16 110.7 . . ? C13 C16 H16 110.7 . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.417 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.070 # Attachment 'CCDC_742702.cif.cif' #============================================================================== data___RG_140308 _database_code_depnum_ccdc_archive 'CCDC 742702' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C17 H18 O5 ' _chemical_formula_moiety 'C17 H18 O5 ' _chemical_formula_weight 302.33 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,+Z 3 +X,1/2-Y,1/2+Z 4 1/2-X,-Y,1/2+Z 5 -X,-Y,-Z 6 1/2+X,1/2-Y,-Z 7 -X,1/2+Y,1/2-Z 8 1/2+X,+Y,1/2-Z #------------------------------------------------------------------------------ _cell_length_a 7.96130(10) _cell_length_b 17.2291(3) _cell_length_c 20.1287(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 2760.97(8) _cell_formula_units_Z 7 _cell_measurement_reflns_used 41301 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 72.5 _cell_measurement_temperature 93.1 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120.00 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.851 _exptl_absorpt_correction_T_max 0.981 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-UNKNOWN' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 50910 _diffrn_reflns_av_R_equivalents 0.065 _diffrn_reflns_theta_max 40.25 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 40.25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 36 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 8696 _reflns_number_gt 35147 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.0633 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 35632 _refine_ls_number_parameters 402 _refine_ls_goodness_of_fit_ref 2.770 _refine_ls_weighting_scheme unit _refine_ls_weighting_details 'w = 1.0' _refine_ls_shift/su_max 21.3889 _refine_diff_density_max 159.00 _refine_diff_density_min -19.60 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 11(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL 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 O(1) O 0.54451(6) 0.16945(2) 0.28023(2) 0.01599(10) Uani 0.90 1 d P . . O(2) O 0.31835(6) 0.07044(2) 0.47581(2) 0.01487(10) Uani 0.90 1 d P . . O(3) O 0.06049(6) 0.12468(3) 0.40139(2) 0.01785(10) Uani 0.90 1 d P . . O(4) O -0.03765(7) 0.00362(3) 0.40021(4) 0.04107(16) Uani 0.91 1 d P . . O(5) O 0.61005(6) -0.14091(3) 0.34815(3) 0.02009(11) Uani 0.91 1 d P . . C(1) C 0.63020(10) 0.22943(4) 0.24472(4) 0.01688(18) Uani 0.86 1 d P . . C(2) C 0.50555(7) 0.18472(3) 0.34527(3) 0.01297(12) Uani 0.90 1 d P . . C(3) C 0.54469(8) 0.25395(4) 0.37864(3) 0.01626(13) Uani 0.92 1 d P . . C(4) C 0.50976(8) 0.26087(4) 0.44623(3) 0.01798(14) Uani 0.92 1 d P . . C(5) C 0.43252(8) 0.20169(4) 0.48230(3) 0.01707(14) Uani 0.91 1 d P . . C(6) C 0.39166(7) 0.13537(3) 0.44715(3) 0.01358(12) Uani 0.91 1 d P . . C(7) C 0.42460(7) 0.12559(3) 0.37984(3) 0.01251(11) Uani 0.92 1 d P . . C(8) C 0.38265(7) 0.04252(3) 0.36246(3) 0.01175(11) Uani 0.91 1 d P . . C(9) C 0.26089(7) 0.02302(3) 0.42071(3) 0.01293(12) Uani 0.90 1 d P . . C(10) C 0.07736(8) 0.04791(4) 0.40638(3) 0.01651(13) Uani 0.90 1 d P . . C(11) C -0.10760(9) 0.15158(4) 0.38646(4) 0.01665(17) Uani 0.87 1 d P . . C(12) C 0.26646(9) -0.06413(4) 0.43426(3) 0.01663(15) Uani 0.91 1 d P . . C(13) C 0.32081(8) -0.10569(3) 0.36917(3) 0.01606(13) Uani 0.90 1 d P . . C(14) C 0.23855(10) -0.06854(4) 0.30673(4) 0.01830(16) Uani 0.89 1 d P . . C(15) C 0.29799(9) 0.01760(4) 0.29745(3) 0.01468(14) Uani 0.89 1 d P . . C(16) C 0.54535(8) -0.00626(3) 0.36961(3) 0.01353(13) Uani 0.90 1 d P . . C(17) C 0.50584(8) -0.09152(3) 0.36106(3) 0.01430(12) Uani 0.90 1 d P . . H(1) H 0.7307(13) 0.2458(5) 0.2665(4) 0.026(3) Uani 0.94 1 c P . . H(2) H 0.5599(12) 0.2737(6) 0.2415(4) 0.031(3) Uani 1.00 1 c P . . H(3) H 0.6578(12) 0.2096(5) 0.2014(5) 0.032(3) Uani 0.98 1 c P . . H(4) H 0.6002(11) 0.2959(5) 0.3557(4) 0.024(3) Uani 0.92 1 c P . . H(5) H 0.5417(11) 0.3075(4) 0.4694(4) 0.019(2) Uani 0.87 1 c P . . H(6) H 0.4081(10) 0.2066(4) 0.5285(4) 0.021(2) Uani 0.94 1 c P . . H(7) H -0.0990(10) 0.2061(6) 0.3799(4) 0.029(3) Uani 0.94 1 c P . . H(8) H -0.1814(12) 0.1404(5) 0.4229(5) 0.037(3) Uani 1.01 1 c P . . H(9) H -0.1470(10) 0.1265(5) 0.3472(5) 0.031(3) Uani 0.99 1 c P . . H(10) H 0.3502(12) -0.0752(5) 0.4695(5) 0.023(3) Uani 0.92 1 c P . . H(11) H 0.1561(12) -0.0828(4) 0.4482(4) 0.025(3) Uani 0.92 1 c P . . H(12) H 0.2950(10) -0.1614(4) 0.3711(4) 0.020(2) Uani 0.94 1 c P . . H(13) H 0.2669(12) -0.0995(5) 0.2667(5) 0.036(3) Uani 0.99 1 c P . . H(14) H 0.1170(13) -0.0696(5) 0.3121(4) 0.025(3) Uani 0.89 1 c P . . H(15) H 0.3798(11) 0.0213(4) 0.2621(4) 0.016(2) Uani 0.94 1 c P . . H(16) H 0.2030(12) 0.0514(4) 0.2858(4) 0.020(2) Uani 0.96 1 c P . . H(17) H 0.6309(12) 0.0094(4) 0.3367(4) 0.022(2) Uani 0.92 1 c P . . H(18) H 0.5964(11) 0.0003(4) 0.4136(4) 0.018(2) Uani 0.88 1 c P . . 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 O(1) 0.0185(2) 0.0136(2) 0.0158(2) -0.00224(15) 0.00286(16) 0.00182(15) O(2) 0.0165(2) 0.0149(2) 0.0132(2) -0.00081(15) 0.00083(15) 0.00071(15) O(3) 0.0123(2) 0.0141(2) 0.0271(2) 0.00229(15) -0.00337(16) 0.00045(17) O(4) 0.0139(2) 0.0190(2) 0.0903(5) -0.00220(17) -0.0067(2) 0.0037(2) O(5) 0.0195(2) 0.0150(2) 0.0257(2) 0.00451(16) 0.00082(18) -0.00144(17) C(1) 0.0158(3) 0.0162(3) 0.0187(3) -0.0022(2) 0.0020(2) 0.0053(2) C(2) 0.0106(2) 0.0126(2) 0.0158(2) 0.00072(18) -0.00047(19) 0.00037(19) C(3) 0.0135(2) 0.0123(2) 0.0230(3) -0.00013(19) -0.0008(2) 0.0002(2) C(4) 0.0168(2) 0.0137(2) 0.0235(3) 0.00189(19) -0.0038(2) -0.0043(2) C(5) 0.0177(2) 0.0169(2) 0.0165(3) 0.0027(2) -0.0021(2) -0.0034(2) C(6) 0.0127(2) 0.0134(2) 0.0147(2) 0.00120(18) -0.00052(19) 0.00047(19) C(7) 0.0114(2) 0.0117(2) 0.0144(2) 0.00043(17) -0.00108(18) -0.00006(18) C(8) 0.0114(2) 0.0109(2) 0.0129(2) -0.00014(17) -0.00038(18) 0.00066(18) C(9) 0.0114(2) 0.0123(2) 0.0151(2) 0.00001(18) 0.00050(19) 0.00077(19) C(10) 0.0130(2) 0.0144(2) 0.0221(3) 0.00089(19) 0.0010(2) 0.0006(2) C(11) 0.0116(3) 0.0171(3) 0.0212(4) 0.0037(2) -0.0019(2) -0.0006(2) C(12) 0.0157(3) 0.0137(2) 0.0205(3) 0.0007(2) 0.0031(2) 0.0040(2) C(13) 0.0157(2) 0.0116(2) 0.0209(3) -0.00074(19) -0.0002(2) 0.0009(2) C(14) 0.0189(3) 0.0138(2) 0.0222(3) -0.0024(2) -0.0066(2) -0.0012(2) C(15) 0.0167(3) 0.0130(2) 0.0144(2) -0.0006(2) -0.0040(2) -0.0003(2) C(16) 0.0123(2) 0.0125(2) 0.0158(3) 0.00091(18) -0.0004(2) 0.0000(2) C(17) 0.0158(2) 0.0135(2) 0.0136(2) 0.00135(19) -0.00089(19) 0.00088(18) H(1) 0.030(7) 0.020(6) 0.027(6) -0.010(4) 0.016(5) 0.014(4) H(2) 0.031(6) 0.037(7) 0.024(5) -0.012(5) 0.008(4) -0.001(4) H(3) 0.039(7) 0.019(5) 0.038(8) -0.018(4) 0.004(5) 0.013(5) H(4) 0.033(6) 0.020(5) 0.019(5) -0.002(4) 0.005(4) -0.007(4) H(5) 0.022(6) 0.007(5) 0.028(6) 0.007(4) -0.004(4) -0.003(4) H(6) 0.027(5) 0.008(4) 0.028(6) -0.007(3) -0.006(4) -0.002(3) H(7) 0.006(4) 0.040(7) 0.040(7) 0.006(4) -0.005(4) 0.003(5) H(8) 0.025(6) 0.046(6) 0.041(7) 0.020(4) -0.001(5) 0.009(5) H(9) 0.014(5) 0.031(6) 0.049(8) 0.020(4) -0.002(4) 0.007(5) H(10) 0.022(6) 0.022(6) 0.026(7) 0.007(4) 0.005(5) 0.007(4) H(11) 0.029(6) 0.011(4) 0.037(7) 0.006(3) 0.002(4) 0.016(4) H(12) 0.017(5) 0.022(5) 0.021(5) -0.007(3) 0.007(3) 0.005(4) H(13) 0.045(7) 0.023(6) 0.040(8) -0.002(4) -0.008(5) 0.018(5) H(14) 0.026(7) 0.026(5) 0.023(6) 0.005(4) -0.007(4) 0.009(4) H(15) 0.029(5) 0.012(4) 0.008(5) 0.002(3) -0.007(4) 0.006(3) H(16) 0.028(6) 0.014(4) 0.017(5) -0.011(4) -0.005(4) -0.002(3) H(17) 0.026(6) 0.015(5) 0.025(5) 0.009(4) -0.011(4) 0.006(4) H(18) 0.027(6) 0.010(4) 0.016(6) 0.003(3) 0.008(4) 0.006(3) #============================================================================== _computing_data_collection PROCESS _computing_cell_refinement PROCESS _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(1) 1.4298(8) yes . . O(1) C(2) 1.3709(7) yes . . O(2) C(6) 1.3874(6) yes . . O(2) C(9) 1.4515(6) yes . . O(3) C(10) 1.3333(8) yes . . O(3) C(11) 1.4477(8) yes . . O(4) C(10) 1.1984(8) yes . . O(5) C(17) 1.2165(7) yes . . C(2) C(3) 1.4039(8) yes . . C(2) C(7) 1.3919(7) yes . . C(3) C(4) 1.3937(8) yes . . C(4) C(5) 1.3946(9) yes . . C(5) C(6) 1.3828(8) yes . . C(6) C(7) 1.3903(8) yes . . C(7) C(8) 1.5107(7) yes . . C(8) C(9) 1.5580(8) yes . . C(8) C(15) 1.5333(8) yes . . C(8) C(16) 1.5508(8) yes . . C(9) C(10) 1.5498(8) yes . . C(9) C(12) 1.5267(8) yes . . C(12) C(13) 1.5545(8) yes . . C(13) C(14) 1.5551(9) yes . . C(13) C(17) 1.5021(8) yes . . C(14) C(15) 1.5689(9) yes . . C(16) C(17) 1.5121(7) yes . . C(1) H(1) 0.955(10) no . . C(1) H(2) 0.949(10) no . . C(1) H(3) 0.962(10) no . . C(3) H(4) 0.964(9) no . . C(4) H(5) 0.963(8) no . . C(5) H(6) 0.955(9) no . . C(11) H(7) 0.950(10) no . . C(11) H(8) 0.960(10) no . . C(11) H(9) 0.955(10) no . . C(12) H(10) 0.992(10) no . . C(12) H(11) 0.977(9) no . . C(13) H(12) 0.983(8) no . . C(14) H(13) 0.992(10) no . . C(14) H(14) 0.974(10) no . . C(15) H(15) 0.967(8) no . . C(15) H(16) 0.983(8) no . . C(16) H(17) 0.988(9) no . . C(16) H(18) 0.980(9) no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(1) O(1) C(2) 116.53(4) yes . . . C(6) O(2) C(9) 105.59(4) yes . . . C(10) O(3) C(11) 115.24(5) yes . . . O(1) C(2) C(3) 124.73(5) yes . . . O(1) C(2) C(7) 116.21(4) yes . . . C(3) C(2) C(7) 119.04(5) yes . . . C(2) C(3) C(4) 119.70(5) yes . . . C(3) C(4) C(5) 122.25(6) yes . . . C(4) C(5) C(6) 116.20(5) yes . . . O(2) C(6) C(5) 123.54(5) yes . . . O(2) C(6) C(7) 112.76(4) yes . . . C(5) C(6) C(7) 123.67(5) yes . . . C(2) C(7) C(6) 119.07(5) yes . . . C(2) C(7) C(8) 132.84(5) yes . . . C(6) C(7) C(8) 107.39(4) yes . . . C(7) C(8) C(9) 99.65(4) yes . . . C(7) C(8) C(15) 124.06(5) yes . . . C(7) C(8) C(16) 107.90(4) yes . . . C(9) C(8) C(15) 107.96(4) yes . . . C(9) C(8) C(16) 109.45(4) yes . . . C(15) C(8) C(16) 107.13(4) yes . . . O(2) C(9) C(8) 104.93(4) yes . . . O(2) C(9) C(10) 106.47(4) yes . . . O(2) C(9) C(12) 114.07(4) yes . . . C(8) C(9) C(10) 112.76(4) yes . . . C(8) C(9) C(12) 109.17(4) yes . . . C(10) C(9) C(12) 109.44(4) yes . . . O(3) C(10) O(4) 123.16(6) yes . . . O(3) C(10) C(9) 112.55(5) yes . . . O(4) C(10) C(9) 124.29(6) yes . . . C(9) C(12) C(13) 108.09(4) yes . . . C(12) C(13) C(14) 111.99(5) yes . . . C(12) C(13) C(17) 106.84(4) yes . . . C(14) C(13) C(17) 104.97(5) yes . . . C(13) C(14) C(15) 111.01(5) yes . . . C(8) C(15) C(14) 107.21(5) yes . . . C(8) C(16) C(17) 110.01(4) yes . . . O(5) C(17) C(13) 125.33(5) yes . . . O(5) C(17) C(16) 124.19(5) yes . . . C(13) C(17) C(16) 110.46(4) yes . . . O(1) C(1) H(1) 112.5(5) no . . . O(1) C(1) H(2) 109.5(5) no . . . O(1) C(1) H(3) 107.8(5) no . . . H(1) C(1) H(2) 106.8(8) no . . . H(1) C(1) H(3) 109.3(8) no . . . H(2) C(1) H(3) 110.9(7) no . . . C(2) C(3) H(4) 120.6(5) no . . . C(4) C(3) H(4) 119.7(5) no . . . C(3) C(4) H(5) 119.5(5) no . . . C(5) C(4) H(5) 118.3(5) no . . . C(4) C(5) H(6) 122.2(4) no . . . C(6) C(5) H(6) 121.6(4) no . . . O(3) C(11) H(7) 106.1(5) no . . . O(3) C(11) H(8) 110.1(5) no . . . O(3) C(11) H(9) 109.3(5) no . . . H(7) C(11) H(8) 110.3(7) no . . . H(7) C(11) H(9) 110.9(8) no . . . H(8) C(11) H(9) 110.0(8) no . . . C(9) C(12) H(10) 109.6(5) no . . . C(9) C(12) H(11) 110.4(4) no . . . C(13) C(12) H(10) 109.1(5) no . . . C(13) C(12) H(11) 109.9(5) no . . . H(10) C(12) H(11) 109.6(7) no . . . C(12) C(13) H(12) 111.1(4) no . . . C(14) C(13) H(12) 110.2(4) no . . . C(17) C(13) H(12) 111.6(4) no . . . C(13) C(14) H(13) 109.8(5) no . . . C(13) C(14) H(14) 108.7(5) no . . . C(15) C(14) H(13) 110.1(5) no . . . C(15) C(14) H(14) 109.3(5) no . . . H(13) C(14) H(14) 107.8(7) no . . . C(8) C(15) H(15) 108.3(5) no . . . C(8) C(15) H(16) 112.1(4) no . . . C(14) C(15) H(15) 110.7(4) no . . . C(14) C(15) H(16) 110.9(4) no . . . H(15) C(15) H(16) 107.6(6) no . . . C(8) C(16) H(17) 111.5(5) no . . . C(8) C(16) H(18) 111.6(5) no . . . C(17) C(16) H(17) 109.4(4) no . . . C(17) C(16) H(18) 107.5(4) no . . . H(17) C(16) H(18) 106.7(7) no . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(1) O(1) C(2) C(3) -0.43(8) ? . . . . C(1) O(1) C(2) C(7) -178.98(5) ? . . . . C(6) O(2) C(9) C(8) 28.52(5) ? . . . . C(6) O(2) C(9) C(10) -91.23(5) ? . . . . C(6) O(2) C(9) C(12) 147.96(4) ? . . . . C(9) O(2) C(6) C(5) 166.84(5) ? . . . . C(9) O(2) C(6) C(7) -15.15(6) ? . . . . C(11) O(3) C(10) O(4) -1.23(9) ? . . . . C(11) O(3) C(10) C(9) 178.61(5) ? . . . . O(1) C(2) C(3) C(4) -175.32(5) ? . . . . O(1) C(2) C(7) C(6) 175.75(4) ? . . . . O(1) C(2) C(7) C(8) 6.73(9) ? . . . . C(3) C(2) C(7) C(6) -2.89(8) ? . . . . C(3) C(2) C(7) C(8) -171.91(5) ? . . . . C(7) C(2) C(3) C(4) 3.20(8) ? . . . . C(2) C(3) C(4) C(5) -1.66(9) ? . . . . C(3) C(4) C(5) C(6) -0.19(9) ? . . . . C(4) C(5) C(6) O(2) 178.29(5) ? . . . . C(4) C(5) C(6) C(7) 0.49(9) ? . . . . O(2) C(6) C(7) C(2) -176.94(4) ? . . . . O(2) C(6) C(7) C(8) -5.36(6) ? . . . . C(5) C(6) C(7) C(2) 1.07(8) ? . . . . C(5) C(6) C(7) C(8) 172.65(5) ? . . . . C(2) C(7) C(8) C(9) -168.44(6) ? . . . . C(2) C(7) C(8) C(15) -48.94(9) ? . . . . C(2) C(7) C(8) C(16) 77.36(7) ? . . . . C(6) C(7) C(8) C(9) 21.61(5) ? . . . . C(6) C(7) C(8) C(15) 141.11(5) ? . . . . C(6) C(7) C(8) C(16) -92.59(5) ? . . . . C(7) C(8) C(9) O(2) -30.23(5) ? . . . . C(7) C(8) C(9) C(10) 85.24(5) ? . . . . C(7) C(8) C(9) C(12) -152.89(4) ? . . . . C(7) C(8) C(15) C(14) -166.53(5) ? . . . . C(7) C(8) C(16) C(17) 173.02(4) ? . . . . C(9) C(8) C(15) C(14) -50.95(6) ? . . . . C(15) C(8) C(9) O(2) -160.95(4) ? . . . . C(15) C(8) C(9) C(10) -45.48(6) ? . . . . C(15) C(8) C(9) C(12) 76.39(5) ? . . . . C(9) C(8) C(16) C(17) 65.52(5) ? . . . . C(16) C(8) C(9) O(2) 82.76(4) ? . . . . C(16) C(8) C(9) C(10) -161.77(4) ? . . . . C(16) C(8) C(9) C(12) -39.90(6) ? . . . . C(15) C(8) C(16) C(17) -51.30(6) ? . . . . C(16) C(8) C(15) C(14) 66.85(6) ? . . . . O(2) C(9) C(10) O(3) 49.27(6) ? . . . . O(2) C(9) C(10) O(4) -130.89(7) ? . . . . O(2) C(9) C(12) C(13) -142.54(5) ? . . . . C(8) C(9) C(10) O(3) -65.27(6) ? . . . . C(8) C(9) C(10) O(4) 114.57(7) ? . . . . C(8) C(9) C(12) C(13) -25.53(6) ? . . . . C(10) C(9) C(12) C(13) 98.32(5) ? . . . . C(12) C(9) C(10) O(3) 173.01(4) ? . . . . C(12) C(9) C(10) O(4) -7.15(9) ? . . . . C(9) C(12) C(13) C(14) -39.75(7) ? . . . . C(9) C(12) C(13) C(17) 74.66(5) ? . . . . C(12) C(13) C(14) C(15) 63.54(7) ? . . . . C(12) C(13) C(17) O(5) 132.20(6) ? . . . . C(12) C(13) C(17) C(16) -49.13(6) ? . . . . C(14) C(13) C(17) O(5) -108.73(7) ? . . . . C(14) C(13) C(17) C(16) 69.93(5) ? . . . . C(17) C(13) C(14) C(15) -52.01(6) ? . . . . C(13) C(14) C(15) C(8) -13.87(7) ? . . . . C(8) C(16) C(17) O(5) 161.39(6) ? . . . . C(8) C(16) C(17) C(13) -17.29(6) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) C(1) 3.4928(9) ? . 8_455 O(1) C(3) 2.4583(7) ? . . O(1) C(7) 2.3457(7) ? . . O(1) C(8) 3.0303(6) ? . . O(1) C(11) 3.5125(8) ? . 1_655 O(1) C(11) 3.5804(8) ? . 8_555 O(1) C(15) 3.2889(8) ? . . O(1) C(16) 3.5216(6) ? . . O(2) O(3) 2.7077(6) ? . . O(2) O(4) 3.4167(7) ? . . O(2) O(4) 3.5847(8) ? . 5_556 O(2) C(5) 2.4407(7) ? . . O(2) C(7) 2.3130(7) ? . . O(2) C(8) 2.3873(7) ? . . O(2) C(10) 2.4052(7) ? . . O(2) C(12) 2.4991(7) ? . . O(2) C(16) 3.0955(7) ? . . O(2) C(16) 3.4759(7) ? . 5_656 O(2) C(17) 3.5879(7) ? . 5_656 O(3) O(2) 2.7077(6) ? . . O(3) O(4) 2.2274(7) ? . . O(3) C(1) 3.4949(8) ? . 8_455 O(3) C(6) 2.7989(7) ? . . O(3) C(7) 2.9311(7) ? . . O(3) C(8) 3.0325(7) ? . . O(3) C(9) 2.4009(7) ? . . O(3) C(15) 3.3699(8) ? . . O(4) O(2) 3.4167(7) ? . . O(4) O(2) 3.5847(8) ? . 5_556 O(4) O(3) 2.2274(7) ? . . O(4) C(8) 3.4962(7) ? . . O(4) C(9) 2.4354(7) ? . . O(4) C(11) 2.6240(8) ? . . O(4) C(12) 2.7738(9) ? . . O(4) C(13) 3.4758(8) ? . . O(4) C(14) 3.1498(10) ? . . O(4) C(15) 3.3877(9) ? . . O(4) C(16) 3.3808(8) ? . 1_455 O(5) C(1) 3.4847(9) ? . 7_645 O(5) C(3) 3.3487(8) ? . 2_645 O(5) C(5) 3.5859(8) ? . 5_656 O(5) C(12) 3.4981(8) ? . . O(5) C(13) 2.4186(7) ? . . O(5) C(14) 3.3162(9) ? . . O(5) C(14) 3.5100(9) ? . 8_555 O(5) C(16) 2.4153(7) ? . . C(1) O(1) 3.4928(9) ? . 8_555 C(1) O(3) 3.4949(8) ? . 8_555 C(1) O(5) 3.4847(9) ? . 7_655 C(1) C(2) 2.3821(9) ? . . C(1) C(2) 3.5783(9) ? . 8_555 C(1) C(3) 2.8122(10) ? . . C(1) C(11) 3.5150(10) ? . 8_555 C(2) C(1) 2.3821(9) ? . . C(2) C(1) 3.5783(9) ? . 8_455 C(2) C(4) 2.4191(8) ? . . C(2) C(5) 2.8340(8) ? . . C(2) C(6) 2.3980(8) ? . . C(2) C(8) 2.6607(7) ? . . C(2) C(11) 3.2402(9) ? . 1_655 C(2) C(15) 3.4565(8) ? . . C(2) C(16) 3.3417(7) ? . . C(3) O(1) 2.4583(7) ? . . C(3) O(5) 3.3487(8) ? . 2_655 C(3) C(1) 2.8122(10) ? . . C(3) C(5) 2.4417(8) ? . . C(3) C(6) 2.7495(8) ? . . C(3) C(7) 2.4095(8) ? . . C(3) C(11) 3.2861(9) ? . 1_655 C(4) C(2) 2.4191(8) ? . . C(4) C(6) 2.3579(8) ? . . C(4) C(7) 2.7709(8) ? . . C(5) O(2) 2.4407(7) ? . . C(5) O(5) 3.5859(8) ? . 5_656 C(5) C(2) 2.8340(8) ? . . C(5) C(3) 2.4417(8) ? . . C(5) C(7) 2.4447(8) ? . . C(5) C(9) 3.5889(8) ? . . C(6) O(3) 2.7989(7) ? . . C(6) C(2) 2.3980(8) ? . . C(6) C(3) 2.7495(8) ? . . C(6) C(4) 2.3579(8) ? . . C(6) C(8) 2.3389(7) ? . . C(6) C(9) 2.2614(7) ? . . C(6) C(10) 3.0340(8) ? . . C(6) C(12) 3.5882(8) ? . . C(6) C(16) 3.1444(7) ? . . C(7) O(1) 2.3457(7) ? . . C(7) O(2) 2.3130(7) ? . . C(7) O(3) 2.9311(7) ? . . C(7) C(3) 2.4095(8) ? . . C(7) C(4) 2.7709(8) ? . . C(7) C(5) 2.4447(8) ? . . C(7) C(9) 2.3449(7) ? . . C(7) C(10) 3.1175(8) ? . . C(7) C(15) 2.6885(8) ? . . C(7) C(16) 2.4753(7) ? . . C(8) O(1) 3.0303(6) ? . . C(8) O(2) 2.3873(7) ? . . C(8) O(3) 3.0325(7) ? . . C(8) O(4) 3.4962(7) ? . . C(8) C(2) 2.6607(7) ? . . C(8) C(6) 2.3389(7) ? . . C(8) C(10) 2.5880(8) ? . . C(8) C(12) 2.5141(8) ? . . C(8) C(13) 2.6041(7) ? . . C(8) C(14) 2.4972(9) ? . . C(8) C(17) 2.5092(7) ? . . C(9) O(3) 2.4009(7) ? . . C(9) O(4) 2.4354(7) ? . . C(9) C(5) 3.5889(8) ? . . C(9) C(6) 2.2614(7) ? . . C(9) C(7) 2.3449(7) ? . . C(9) C(13) 2.4943(7) ? . . C(9) C(14) 2.7899(9) ? . . C(9) C(15) 2.5003(8) ? . . C(9) C(16) 2.5380(8) ? . . C(9) C(17) 3.0231(8) ? . . C(10) O(2) 2.4052(7) ? . . C(10) C(6) 3.0340(8) ? . . C(10) C(7) 3.1175(8) ? . . C(10) C(8) 2.5880(8) ? . . C(10) C(11) 2.3493(9) ? . . C(10) C(12) 2.5115(9) ? . . C(10) C(13) 3.3647(8) ? . . C(10) C(14) 3.1138(9) ? . . C(10) C(15) 2.8575(8) ? . . C(11) O(1) 3.5125(8) ? . 1_455 C(11) O(1) 3.5804(8) ? . 8_455 C(11) O(4) 2.6240(8) ? . . C(11) C(1) 3.5150(10) ? . 8_455 C(11) C(2) 3.2402(9) ? . 1_455 C(11) C(3) 3.2861(9) ? . 1_455 C(11) C(10) 2.3493(9) ? . . C(12) O(2) 2.4991(7) ? . . C(12) O(4) 2.7738(9) ? . . C(12) O(5) 3.4981(8) ? . . C(12) C(6) 3.5882(8) ? . . C(12) C(8) 2.5141(8) ? . . C(12) C(10) 2.5115(9) ? . . C(12) C(14) 2.5777(10) ? . . C(12) C(15) 3.1031(8) ? . . C(12) C(16) 2.7600(9) ? . . C(12) C(17) 2.4547(9) ? . . C(13) O(4) 3.4758(8) ? . . C(13) O(5) 2.4186(7) ? . . C(13) C(8) 2.6041(7) ? . . C(13) C(9) 2.4943(7) ? . . C(13) C(10) 3.3647(8) ? . . C(13) C(15) 2.5747(8) ? . . C(13) C(16) 2.4760(8) ? . . C(14) O(4) 3.1498(10) ? . . C(14) O(5) 3.3162(9) ? . . C(14) O(5) 3.5100(9) ? . 8_455 C(14) C(8) 2.4972(9) ? . . C(14) C(9) 2.7899(9) ? . . C(14) C(10) 3.1138(9) ? . . C(14) C(12) 2.5777(10) ? . . C(14) C(16) 2.9528(9) ? . . C(14) C(17) 2.4251(10) ? . . C(15) O(1) 3.2889(8) ? . . C(15) O(3) 3.3699(8) ? . . C(15) O(4) 3.3877(9) ? . . C(15) C(2) 3.4565(8) ? . . C(15) C(7) 2.6885(8) ? . . C(15) C(9) 2.5003(8) ? . . C(15) C(10) 2.8575(8) ? . . C(15) C(12) 3.1031(8) ? . . C(15) C(13) 2.5747(8) ? . . C(15) C(16) 2.4813(9) ? . . C(15) C(17) 2.8129(8) ? . . C(16) O(1) 3.5216(6) ? . . C(16) O(2) 3.0955(7) ? . . C(16) O(2) 3.4759(7) ? . 5_656 C(16) O(4) 3.3808(8) ? . 1_655 C(16) O(5) 2.4153(7) ? . . C(16) C(2) 3.3417(7) ? . . C(16) C(6) 3.1444(7) ? . . C(16) C(7) 2.4753(7) ? . . C(16) C(9) 2.5380(8) ? . . C(16) C(12) 2.7600(9) ? . . C(16) C(13) 2.4760(8) ? . . C(16) C(14) 2.9528(9) ? . . C(16) C(15) 2.4813(9) ? . . C(17) O(2) 3.5879(7) ? . 5_656 C(17) C(8) 2.5092(7) ? . . C(17) C(9) 3.0231(8) ? . . C(17) C(12) 2.4547(9) ? . . C(17) C(14) 2.4251(10) ? . . C(17) C(15) 2.8129(8) ? . . O(1) H(1) 2.001(9) ? . . O(1) H(1) 2.976(10) ? . 8_455 O(1) H(2) 1.962(10) ? . . O(1) H(3) 1.953(10) ? . . O(1) H(3) 3.177(10) ? . 8_455 O(1) H(4) 2.692(8) ? . . O(1) H(7) 3.533(8) ? . 1_655 O(1) H(7) 3.478(9) ? . 8_555 O(1) H(9) 2.898(9) ? . 1_655 O(1) H(9) 3.074(10) ? . 8_555 O(1) H(15) 2.893(8) ? . . O(1) H(16) 3.397(8) ? . . O(1) H(16) 2.738(8) ? . 8_555 O(1) H(17) 3.062(8) ? . . O(2) H(5) 3.239(8) ? . 6_456 O(2) H(6) 2.672(7) ? . . O(2) H(10) 2.525(8) ? . . O(2) H(10) 2.861(9) ? . 5_656 O(2) H(11) 2.991(8) ? . . O(2) H(18) 2.816(9) ? . . O(2) H(18) 2.628(9) ? . 5_656 O(3) H(3) 2.650(10) ? . 8_455 O(3) H(5) 2.855(8) ? . 6_456 O(3) H(6) 3.451(8) ? . 6_456 O(3) H(7) 1.940(9) ? . . O(3) H(8) 1.993(9) ? . . O(3) H(9) 1.980(9) ? . . O(3) H(11) 3.558(9) ? . 5_556 O(3) H(16) 2.880(8) ? . . O(4) H(7) 3.545(10) ? . . O(4) H(8) 2.660(9) ? . . O(4) H(9) 2.525(9) ? . . O(4) H(11) 2.352(9) ? . . O(4) H(11) 3.473(9) ? . 5_556 O(4) H(14) 2.500(9) ? . . O(4) H(15) 3.346(8) ? . 8_455 O(4) H(16) 3.107(8) ? . . O(4) H(17) 2.934(9) ? . 1_455 O(4) H(18) 2.926(9) ? . 1_455 O(5) H(1) 2.849(9) ? . 2_645 O(5) H(2) 2.692(9) ? . 7_645 O(5) H(3) 3.489(9) ? . 7_645 O(5) H(4) 2.556(9) ? . 2_645 O(5) H(6) 2.732(9) ? . 5_656 O(5) H(7) 2.714(10) ? . 2_545 O(5) H(10) 3.395(9) ? . . O(5) H(12) 2.574(8) ? . . O(5) H(13) 3.264(10) ? . . O(5) H(13) 2.723(10) ? . 8_555 O(5) H(14) 3.452(9) ? . 8_555 O(5) H(17) 2.604(8) ? . . O(5) H(18) 2.769(8) ? . . C(1) H(1) 3.201(10) ? . 8_455 C(1) H(2) 3.516(9) ? . 8_555 C(1) H(4) 2.521(8) ? . . C(1) H(7) 3.496(9) ? . 1_655 C(1) H(7) 3.128(9) ? . 8_555 C(1) H(9) 3.248(10) ? . 1_655 C(1) H(9) 3.382(9) ? . 8_555 C(1) H(12) 3.053(8) ? . 7_655 C(1) H(13) 3.067(9) ? . 7_655 C(1) H(16) 3.181(7) ? . 8_555 C(2) H(1) 2.614(9) ? . . C(2) H(1) 3.311(9) ? . 8_455 C(2) H(2) 2.628(9) ? . . C(2) H(3) 3.169(11) ? . . C(2) H(3) 2.955(10) ? . 8_455 C(2) H(4) 2.068(9) ? . . C(2) H(5) 3.286(8) ? . . C(2) H(7) 3.246(8) ? . 1_655 C(2) H(8) 3.039(9) ? . 1_655 C(2) H(9) 2.943(8) ? . 1_655 C(2) H(15) 3.425(8) ? . . C(2) H(16) 3.537(8) ? . . C(2) H(17) 3.187(8) ? . . C(2) H(18) 3.536(8) ? . . C(3) H(1) 2.703(9) ? . . C(3) H(2) 2.785(8) ? . . C(3) H(3) 3.559(10) ? . 8_455 C(3) H(5) 2.047(8) ? . . C(3) H(6) 3.310(9) ? . . C(3) H(6) 3.510(8) ? . 6_556 C(3) H(7) 2.955(8) ? . 1_655 C(3) H(8) 3.062(9) ? . 1_655 C(3) H(9) 3.354(8) ? . 1_655 C(3) H(11) 3.525(8) ? . 2_555 C(3) H(12) 3.076(8) ? . 2_555 C(3) H(14) 3.562(9) ? . 2_555 C(4) H(4) 2.050(8) ? . . C(4) H(6) 2.068(8) ? . . C(4) H(6) 3.260(8) ? . 6_556 C(4) H(7) 3.518(8) ? . 1_655 C(4) H(8) 3.251(9) ? . 1_655 C(4) H(8) 3.485(10) ? . 6_556 C(4) H(11) 3.000(8) ? . 2_555 C(4) H(12) 3.157(8) ? . 2_555 C(5) H(4) 3.303(8) ? . . C(5) H(5) 2.035(8) ? . . C(5) H(5) 3.264(9) ? . 6_456 C(5) H(7) 3.206(9) ? . 6_556 C(5) H(8) 3.462(9) ? . 1_655 C(5) H(8) 3.444(9) ? . 6_556 C(5) H(10) 2.947(9) ? . 5_656 C(6) H(5) 3.228(8) ? . . C(6) H(5) 3.399(9) ? . 6_456 C(6) H(6) 2.051(8) ? . . C(6) H(8) 3.435(9) ? . 1_655 C(6) H(10) 2.849(9) ? . 5_656 C(6) H(18) 2.920(8) ? . . C(7) H(3) 3.046(10) ? . 8_455 C(7) H(4) 3.286(9) ? . . C(7) H(6) 3.305(9) ? . . C(7) H(8) 3.264(9) ? . 1_655 C(7) H(9) 3.474(8) ? . 1_655 C(7) H(15) 2.996(8) ? . . C(7) H(16) 2.886(8) ? . . C(7) H(17) 2.732(8) ? . . C(7) H(18) 2.644(8) ? . . C(8) H(10) 2.970(9) ? . . C(8) H(11) 3.301(9) ? . . C(8) H(12) 3.586(8) ? . . C(8) H(13) 3.248(10) ? . . C(8) H(14) 3.039(9) ? . . C(8) H(15) 2.054(8) ? . . C(8) H(16) 2.109(8) ? . . C(8) H(17) 2.122(9) ? . . C(8) H(18) 2.117(9) ? . . C(9) H(10) 2.081(9) ? . . C(9) H(11) 2.080(8) ? . . C(9) H(12) 3.342(8) ? . . C(9) H(14) 2.939(9) ? . . C(9) H(15) 3.331(8) ? . . C(9) H(16) 2.798(8) ? . . C(9) H(17) 3.405(9) ? . . C(9) H(18) 2.704(9) ? . . C(9) H(18) 3.547(9) ? . 5_656 C(10) H(3) 3.589(9) ? . 8_455 C(10) H(5) 3.541(8) ? . 6_456 C(10) H(7) 3.111(10) ? . . C(10) H(8) 2.626(9) ? . . C(10) H(9) 2.538(9) ? . . C(10) H(10) 3.291(9) ? . . C(10) H(11) 2.485(8) ? . . C(10) H(11) 3.519(9) ? . 5_556 C(10) H(14) 2.793(9) ? . . C(10) H(16) 2.626(8) ? . . C(11) H(1) 3.181(9) ? . 1_455 C(11) H(2) 3.583(9) ? . 8_455 C(11) H(3) 2.931(10) ? . 8_455 C(11) H(4) 3.461(9) ? . 1_455 C(11) H(5) 3.213(9) ? . 6_456 C(11) H(6) 2.985(8) ? . 6_456 C(11) H(11) 3.553(9) ? . 5_556 C(11) H(17) 3.368(8) ? . 1_455 C(11) H(18) 3.555(8) ? . 1_455 C(12) H(5) 3.378(8) ? . 2_545 C(12) H(8) 3.232(10) ? . 5_556 C(12) H(12) 2.116(8) ? . . C(12) H(13) 3.426(10) ? . . C(12) H(14) 2.733(9) ? . . C(12) H(18) 2.882(9) ? . . C(12) H(18) 3.433(9) ? . 5_656 C(13) H(2) 3.190(9) ? . 7_645 C(13) H(3) 3.488(9) ? . 7_645 C(13) H(6) 3.453(8) ? . 5_656 C(13) H(10) 2.099(10) ? . . C(13) H(11) 2.099(9) ? . . C(13) H(13) 2.108(10) ? . . C(13) H(14) 2.083(10) ? . . C(13) H(15) 3.107(8) ? . . C(13) H(16) 3.320(8) ? . . C(13) H(17) 3.233(9) ? . . C(13) H(18) 2.992(8) ? . . C(14) H(1) 3.531(8) ? . 7_645 C(14) H(2) 3.302(10) ? . 7_645 C(14) H(10) 3.396(10) ? . . C(14) H(11) 2.933(9) ? . . C(14) H(12) 2.107(8) ? . . C(14) H(15) 2.114(8) ? . . C(14) H(15) 3.532(8) ? . 8_455 C(14) H(16) 2.128(7) ? . . C(14) H(17) 3.453(9) ? . . C(14) H(17) 3.297(8) ? . 8_455 C(15) H(3) 3.492(9) ? . 8_455 C(15) H(9) 3.490(10) ? . 8_555 C(15) H(12) 3.422(8) ? . . C(15) H(13) 2.125(9) ? . . C(15) H(14) 2.103(9) ? . . C(15) H(15) 3.539(8) ? . 8_455 C(15) H(17) 2.770(9) ? . . C(15) H(17) 3.013(9) ? . 8_455 C(15) H(18) 3.346(9) ? . . C(16) H(8) 3.503(9) ? . 1_655 C(16) H(9) 3.381(8) ? . 1_655 C(16) H(10) 2.804(9) ? . . C(16) H(12) 3.334(8) ? . . C(16) H(13) 3.433(10) ? . . C(16) H(15) 2.578(8) ? . . C(16) H(16) 3.356(9) ? . . C(16) H(16) 3.514(8) ? . 8_555 C(17) H(2) 3.150(9) ? . 7_645 C(17) H(6) 3.056(8) ? . 5_656 C(17) H(7) 3.586(10) ? . 2_545 C(17) H(10) 2.525(10) ? . . C(17) H(11) 3.294(9) ? . . C(17) H(12) 2.075(8) ? . . C(17) H(13) 2.691(10) ? . . C(17) H(13) 3.310(10) ? . 8_555 C(17) H(14) 3.271(10) ? . . C(17) H(15) 2.959(8) ? . . C(17) H(17) 2.062(8) ? . . C(17) H(18) 2.035(8) ? . . H(1) O(1) 2.001(9) ? . . H(1) O(1) 2.976(10) ? . 8_555 H(1) O(5) 2.849(9) ? . 2_655 H(1) C(1) 3.201(10) ? . 8_555 H(1) C(2) 2.614(9) ? . . H(1) C(2) 3.311(9) ? . 8_555 H(1) C(3) 2.703(9) ? . . H(1) C(11) 3.181(9) ? . 1_655 H(1) C(14) 3.531(8) ? . 7_655 H(1) H(2) 1.528(14) ? . . H(1) H(2) 2.670(14) ? . 8_555 H(1) H(3) 1.564(14) ? . . H(1) H(3) 3.517(14) ? . 8_555 H(1) H(4) 2.246(13) ? . . H(1) H(7) 2.742(13) ? . 1_655 H(1) H(9) 2.795(13) ? . 1_655 H(1) H(12) 3.205(12) ? . 7_655 H(1) H(13) 2.748(13) ? . 7_655 H(1) H(16) 3.517(11) ? . 8_555 H(2) O(1) 1.962(10) ? . . H(2) O(5) 2.692(9) ? . 7_655 H(2) C(1) 3.516(9) ? . 8_455 H(2) C(2) 2.628(9) ? . . H(2) C(3) 2.785(8) ? . . H(2) C(11) 3.583(9) ? . 8_555 H(2) C(13) 3.190(9) ? . 7_655 H(2) C(14) 3.302(10) ? . 7_655 H(2) C(17) 3.150(9) ? . 7_655 H(2) H(1) 1.528(14) ? . . H(2) H(1) 2.670(14) ? . 8_455 H(2) H(3) 1.574(14) ? . . H(2) H(3) 3.577(14) ? . 8_455 H(2) H(4) 2.352(12) ? . . H(2) H(7) 2.988(13) ? . 8_555 H(2) H(9) 3.512(13) ? . 8_555 H(2) H(12) 2.777(12) ? . 7_655 H(2) H(13) 3.435(14) ? . 2_555 H(2) H(13) 2.588(14) ? . 7_655 H(2) H(14) 3.360(13) ? . 2_555 H(3) O(1) 1.953(10) ? . . H(3) O(1) 3.177(10) ? . 8_555 H(3) O(3) 2.650(10) ? . 8_555 H(3) O(5) 3.489(9) ? . 7_655 H(3) C(2) 3.169(11) ? . . H(3) C(2) 2.955(10) ? . 8_555 H(3) C(3) 3.559(10) ? . 8_555 H(3) C(7) 3.046(10) ? . 8_555 H(3) C(10) 3.589(9) ? . 8_555 H(3) C(11) 2.931(10) ? . 8_555 H(3) C(13) 3.488(9) ? . 7_655 H(3) C(15) 3.492(9) ? . 8_555 H(3) H(1) 1.564(14) ? . . H(3) H(1) 3.517(14) ? . 8_455 H(3) H(2) 1.574(14) ? . . H(3) H(2) 3.577(14) ? . 8_555 H(3) H(4) 3.473(13) ? . . H(3) H(7) 2.619(13) ? . 8_555 H(3) H(9) 2.983(13) ? . 8_555 H(3) H(12) 2.684(12) ? . 7_655 H(3) H(13) 3.403(13) ? . 7_655 H(3) H(16) 2.762(11) ? . 8_555 H(4) O(1) 2.692(8) ? . . H(4) O(5) 2.556(9) ? . 2_655 H(4) C(1) 2.521(8) ? . . H(4) C(2) 2.068(9) ? . . H(4) C(4) 2.050(8) ? . . H(4) C(5) 3.303(8) ? . . H(4) C(7) 3.286(9) ? . . H(4) C(11) 3.461(9) ? . 1_655 H(4) H(1) 2.246(13) ? . . H(4) H(2) 2.352(12) ? . . H(4) H(3) 3.473(13) ? . . H(4) H(5) 2.345(12) ? . . H(4) H(6) 3.382(12) ? . 6_556 H(4) H(7) 2.893(12) ? . 1_655 H(4) H(8) 3.468(13) ? . 1_655 H(4) H(9) 3.550(12) ? . 1_655 H(4) H(11) 3.464(12) ? . 2_555 H(4) H(12) 3.246(12) ? . 2_555 H(4) H(13) 3.231(13) ? . 7_655 H(4) H(14) 3.022(13) ? . 2_555 H(5) O(2) 3.239(8) ? . 6_556 H(5) O(3) 2.855(8) ? . 6_556 H(5) C(2) 3.286(8) ? . . H(5) C(3) 2.047(8) ? . . H(5) C(5) 2.035(8) ? . . H(5) C(5) 3.264(9) ? . 6_556 H(5) C(6) 3.228(8) ? . . H(5) C(6) 3.399(9) ? . 6_556 H(5) C(10) 3.541(8) ? . 6_556 H(5) C(11) 3.213(9) ? . 6_556 H(5) C(12) 3.378(8) ? . 2_555 H(5) H(4) 2.345(12) ? . . H(5) H(6) 2.359(11) ? . . H(5) H(6) 2.927(12) ? . 6_556 H(5) H(7) 3.241(13) ? . 6_556 H(5) H(8) 2.942(13) ? . 6_556 H(5) H(11) 2.497(12) ? . 2_555 H(5) H(12) 3.375(12) ? . 2_555 H(6) O(2) 2.672(7) ? . . H(6) O(3) 3.451(8) ? . 6_556 H(6) O(5) 2.732(9) ? . 5_656 H(6) C(3) 3.310(9) ? . . H(6) C(3) 3.510(8) ? . 6_456 H(6) C(4) 2.068(8) ? . . H(6) C(4) 3.260(8) ? . 6_456 H(6) C(6) 2.051(8) ? . . H(6) C(7) 3.305(9) ? . . H(6) C(11) 2.985(8) ? . 6_556 H(6) C(13) 3.453(8) ? . 5_656 H(6) C(17) 3.056(8) ? . 5_656 H(6) H(4) 3.382(12) ? . 6_456 H(6) H(5) 2.359(11) ? . . H(6) H(5) 2.927(12) ? . 6_456 H(6) H(7) 2.379(13) ? . 6_556 H(6) H(8) 2.899(12) ? . 6_556 H(6) H(10) 2.972(12) ? . 5_656 H(6) H(12) 3.206(12) ? . 5_656 H(7) O(1) 3.533(8) ? . 1_455 H(7) O(1) 3.478(9) ? . 8_455 H(7) O(3) 1.940(9) ? . . H(7) O(4) 3.545(10) ? . . H(7) O(5) 2.714(10) ? . 2_555 H(7) C(1) 3.496(9) ? . 1_455 H(7) C(1) 3.128(9) ? . 8_455 H(7) C(2) 3.246(8) ? . 1_455 H(7) C(3) 2.955(8) ? . 1_455 H(7) C(4) 3.518(8) ? . 1_455 H(7) C(5) 3.206(9) ? . 6_456 H(7) C(10) 3.111(10) ? . . H(7) C(17) 3.586(10) ? . 2_555 H(7) H(1) 2.742(13) ? . 1_455 H(7) H(2) 2.988(13) ? . 8_455 H(7) H(3) 2.619(13) ? . 8_455 H(7) H(4) 2.893(12) ? . 1_455 H(7) H(5) 3.241(13) ? . 6_456 H(7) H(6) 2.379(13) ? . 6_456 H(7) H(8) 1.568(13) ? . . H(7) H(9) 1.569(14) ? . . H(7) H(12) 3.332(12) ? . 2_555 H(8) O(3) 1.993(9) ? . . H(8) O(4) 2.660(9) ? . . H(8) C(2) 3.039(9) ? . 1_455 H(8) C(3) 3.062(9) ? . 1_455 H(8) C(4) 3.251(9) ? . 1_455 H(8) C(4) 3.485(10) ? . 6_456 H(8) C(5) 3.462(9) ? . 1_455 H(8) C(5) 3.444(9) ? . 6_456 H(8) C(6) 3.435(9) ? . 1_455 H(8) C(7) 3.264(9) ? . 1_455 H(8) C(10) 2.626(9) ? . . H(8) C(12) 3.232(10) ? . 5_556 H(8) C(16) 3.503(9) ? . 1_455 H(8) H(4) 3.468(13) ? . 1_455 H(8) H(5) 2.942(13) ? . 6_456 H(8) H(6) 2.899(12) ? . 6_456 H(8) H(7) 1.568(13) ? . . H(8) H(9) 1.568(15) ? . . H(8) H(10) 2.785(14) ? . 5_556 H(8) H(11) 2.784(14) ? . 5_556 H(8) H(17) 3.217(13) ? . 1_455 H(8) H(18) 2.998(12) ? . 1_455 H(9) O(1) 2.898(9) ? . 1_455 H(9) O(1) 3.074(10) ? . 8_455 H(9) O(3) 1.980(9) ? . . H(9) O(4) 2.525(9) ? . . H(9) C(1) 3.248(10) ? . 1_455 H(9) C(1) 3.382(9) ? . 8_455 H(9) C(2) 2.943(8) ? . 1_455 H(9) C(3) 3.354(8) ? . 1_455 H(9) C(7) 3.474(8) ? . 1_455 H(9) C(10) 2.538(9) ? . . H(9) C(15) 3.490(10) ? . 8_455 H(9) C(16) 3.381(8) ? . 1_455 H(9) H(1) 2.795(13) ? . 1_455 H(9) H(2) 3.512(13) ? . 8_455 H(9) H(3) 2.983(13) ? . 8_455 H(9) H(4) 3.550(12) ? . 1_455 H(9) H(7) 1.569(14) ? . . H(9) H(8) 1.568(15) ? . . H(9) H(15) 2.857(13) ? . 8_455 H(9) H(16) 3.311(12) ? . . H(9) H(16) 3.203(13) ? . 8_455 H(9) H(17) 2.691(12) ? . 1_455 H(9) H(18) 3.268(12) ? . 1_455 H(10) O(2) 2.525(8) ? . . H(10) O(2) 2.861(9) ? . 5_656 H(10) O(5) 3.395(9) ? . . H(10) C(5) 2.947(9) ? . 5_656 H(10) C(6) 2.849(9) ? . 5_656 H(10) C(8) 2.970(9) ? . . H(10) C(9) 2.081(9) ? . . H(10) C(10) 3.291(9) ? . . H(10) C(13) 2.099(10) ? . . H(10) C(14) 3.396(10) ? . . H(10) C(16) 2.804(9) ? . . H(10) C(17) 2.525(10) ? . . H(10) H(6) 2.972(12) ? . 5_656 H(10) H(8) 2.785(14) ? . 5_556 H(10) H(11) 1.609(13) ? . . H(10) H(12) 2.515(12) ? . . H(10) H(18) 2.608(13) ? . . H(10) H(18) 2.718(13) ? . 5_656 H(11) O(2) 2.991(8) ? . . H(11) O(3) 3.558(9) ? . 5_556 H(11) O(4) 2.352(9) ? . . H(11) O(4) 3.473(9) ? . 5_556 H(11) C(3) 3.525(8) ? . 2_545 H(11) C(4) 3.000(8) ? . 2_545 H(11) C(8) 3.301(9) ? . . H(11) C(9) 2.080(8) ? . . H(11) C(10) 2.485(8) ? . . H(11) C(10) 3.519(9) ? . 5_556 H(11) C(11) 3.553(9) ? . 5_556 H(11) C(13) 2.099(9) ? . . H(11) C(14) 2.933(9) ? . . H(11) C(17) 3.294(9) ? . . H(11) H(4) 3.464(12) ? . 2_545 H(11) H(5) 2.497(12) ? . 2_545 H(11) H(8) 2.784(14) ? . 5_556 H(11) H(10) 1.609(13) ? . . H(11) H(12) 2.339(12) ? . . H(11) H(14) 2.767(13) ? . . H(12) O(5) 2.574(8) ? . . H(12) C(1) 3.053(8) ? . 7_645 H(12) C(3) 3.076(8) ? . 2_545 H(12) C(4) 3.157(8) ? . 2_545 H(12) C(8) 3.586(8) ? . . H(12) C(9) 3.342(8) ? . . H(12) C(12) 2.116(8) ? . . H(12) C(14) 2.107(8) ? . . H(12) C(15) 3.422(8) ? . . H(12) C(16) 3.334(8) ? . . H(12) C(17) 2.075(8) ? . . H(12) H(1) 3.205(12) ? . 7_645 H(12) H(2) 2.777(12) ? . 7_645 H(12) H(3) 2.684(12) ? . 7_645 H(12) H(4) 3.246(12) ? . 2_545 H(12) H(5) 3.375(12) ? . 2_545 H(12) H(6) 3.206(12) ? . 5_656 H(12) H(7) 3.332(12) ? . 2_545 H(12) H(10) 2.515(12) ? . . H(12) H(11) 2.339(12) ? . . H(12) H(13) 2.366(13) ? . . H(12) H(14) 2.433(12) ? . . H(13) O(5) 3.264(10) ? . . H(13) O(5) 2.723(10) ? . 8_455 H(13) C(1) 3.067(9) ? . 7_645 H(13) C(8) 3.248(10) ? . . H(13) C(12) 3.426(10) ? . . H(13) C(13) 2.108(10) ? . . H(13) C(15) 2.125(9) ? . . H(13) C(16) 3.433(10) ? . . H(13) C(17) 2.691(10) ? . . H(13) C(17) 3.310(10) ? . 8_455 H(13) H(1) 2.748(13) ? . 7_645 H(13) H(2) 3.435(14) ? . 2_545 H(13) H(2) 2.588(14) ? . 7_645 H(13) H(3) 3.403(13) ? . 7_645 H(13) H(4) 3.231(13) ? . 7_645 H(13) H(12) 2.366(13) ? . . H(13) H(14) 1.589(14) ? . . H(13) H(14) 3.248(14) ? . 8_555 H(13) H(15) 2.269(12) ? . . H(13) H(16) 2.677(12) ? . . H(13) H(17) 3.004(13) ? . 8_455 H(14) O(4) 2.500(9) ? . . H(14) O(5) 3.452(9) ? . 8_455 H(14) C(3) 3.562(9) ? . 2_545 H(14) C(8) 3.039(9) ? . . H(14) C(9) 2.939(9) ? . . H(14) C(10) 2.793(9) ? . . H(14) C(12) 2.733(9) ? . . H(14) C(13) 2.083(10) ? . . H(14) C(15) 2.103(9) ? . . H(14) C(17) 3.271(10) ? . . H(14) H(2) 3.360(13) ? . 2_545 H(14) H(4) 3.022(13) ? . 2_545 H(14) H(11) 2.767(13) ? . . H(14) H(12) 2.433(12) ? . . H(14) H(13) 1.589(14) ? . . H(14) H(13) 3.248(14) ? . 8_455 H(14) H(15) 2.801(13) ? . . H(14) H(15) 2.872(12) ? . 8_455 H(14) H(16) 2.258(12) ? . . H(14) H(17) 3.292(12) ? . 8_455 H(15) O(1) 2.893(8) ? . . H(15) O(4) 3.346(8) ? . 8_555 H(15) C(2) 3.425(8) ? . . H(15) C(7) 2.996(8) ? . . H(15) C(8) 2.054(8) ? . . H(15) C(9) 3.331(8) ? . . H(15) C(13) 3.107(8) ? . . H(15) C(14) 2.114(8) ? . . H(15) C(14) 3.532(8) ? . 8_555 H(15) C(15) 3.539(8) ? . 8_555 H(15) C(16) 2.578(8) ? . . H(15) C(17) 2.959(8) ? . . H(15) H(9) 2.857(13) ? . 8_555 H(15) H(13) 2.269(12) ? . . H(15) H(14) 2.801(13) ? . . H(15) H(14) 2.872(12) ? . 8_555 H(15) H(16) 1.574(12) ? . . H(15) H(16) 2.796(12) ? . 8_555 H(15) H(17) 2.509(12) ? . . H(15) H(17) 2.814(12) ? . 8_455 H(15) H(18) 3.522(12) ? . . H(16) O(1) 3.397(8) ? . . H(16) O(1) 2.738(8) ? . 8_455 H(16) O(3) 2.880(8) ? . . H(16) O(4) 3.107(8) ? . . H(16) C(1) 3.181(7) ? . 8_455 H(16) C(2) 3.537(8) ? . . H(16) C(7) 2.886(8) ? . . H(16) C(8) 2.109(8) ? . . H(16) C(9) 2.798(8) ? . . H(16) C(10) 2.626(8) ? . . H(16) C(13) 3.320(8) ? . . H(16) C(14) 2.128(7) ? . . H(16) C(16) 3.356(9) ? . . H(16) C(16) 3.514(8) ? . 8_455 H(16) H(1) 3.517(11) ? . 8_455 H(16) H(3) 2.762(11) ? . 8_455 H(16) H(9) 3.311(12) ? . . H(16) H(9) 3.203(13) ? . 8_555 H(16) H(13) 2.677(12) ? . . H(16) H(14) 2.258(12) ? . . H(16) H(15) 1.574(12) ? . . H(16) H(15) 2.796(12) ? . 8_455 H(16) H(17) 2.633(11) ? . 8_455 H(17) O(1) 3.062(8) ? . . H(17) O(4) 2.934(9) ? . 1_655 H(17) O(5) 2.604(8) ? . . H(17) C(2) 3.187(8) ? . . H(17) C(7) 2.732(8) ? . . H(17) C(8) 2.122(9) ? . . H(17) C(9) 3.405(9) ? . . H(17) C(11) 3.368(8) ? . 1_655 H(17) C(13) 3.233(9) ? . . H(17) C(14) 3.453(9) ? . . H(17) C(14) 3.297(8) ? . 8_555 H(17) C(15) 2.770(9) ? . . H(17) C(15) 3.013(9) ? . 8_555 H(17) C(17) 2.062(8) ? . . H(17) H(8) 3.217(13) ? . 1_655 H(17) H(9) 2.691(12) ? . 1_655 H(17) H(13) 3.004(13) ? . 8_555 H(17) H(14) 3.292(12) ? . 8_555 H(17) H(15) 2.509(12) ? . . H(17) H(15) 2.814(12) ? . 8_555 H(17) H(16) 2.633(11) ? . 8_555 H(17) H(18) 1.579(13) ? . . H(18) O(2) 2.816(9) ? . . H(18) O(2) 2.628(9) ? . 5_656 H(18) O(4) 2.926(9) ? . 1_655 H(18) O(5) 2.769(8) ? . . H(18) C(2) 3.536(8) ? . . H(18) C(6) 2.920(8) ? . . H(18) C(7) 2.644(8) ? . . H(18) C(8) 2.117(9) ? . . H(18) C(9) 2.704(9) ? . . H(18) C(9) 3.547(9) ? . 5_656 H(18) C(11) 3.555(8) ? . 1_655 H(18) C(12) 2.882(9) ? . . H(18) C(12) 3.433(9) ? . 5_656 H(18) C(13) 2.992(8) ? . . H(18) C(15) 3.346(9) ? . . H(18) C(17) 2.035(8) ? . . H(18) H(8) 2.998(12) ? . 1_655 H(18) H(9) 3.268(12) ? . 1_655 H(18) H(10) 2.608(13) ? . . H(18) H(10) 2.718(13) ? . 5_656 H(18) H(15) 3.522(12) ? . . H(18) H(17) 1.579(13) ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment 'CCDC_742962.cif.cif' #============================================================================== data___M0807001 _database_code_depnum_ccdc_archive 'CCDC 742962' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H18 O4 ' _chemical_formula_moiety 'C16 H18 O4 ' _chemical_formula_weight 274.32 _chemical_melting_point ? _chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk' #============================================================================== # CRYSTAL DATA _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_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z #------------------------------------------------------------------------------ _cell_length_a 6.746(3) _cell_length_b 8.675(3) _cell_length_c 11.483(4) _cell_angle_alpha 102.121(4) _cell_angle_beta 98.334(3) _cell_angle_gamma 104.318(5) _cell_volume 622.7(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1516 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 31.4 _cell_measurement_temperature 110.1 #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292.00 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 0.981 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 14.63 _diffrn_reflns_number 9568 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_theta_max 31.04 _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 31.04 _diffrn_measured_fraction_theta_full 0.886 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5075 _reflns_number_gt 8079 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.0427 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 8104 _refine_ls_number_parameters 439 _refine_ls_goodness_of_fit_ref 6.924 _refine_ls_weighting_scheme unit _refine_ls_weighting_details 'w = 1.0' _refine_ls_shift/su_max 9.1257 _refine_diff_density_max 57.50 _refine_diff_density_min -9.46 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 87(3) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1542 Friedel Pairs' _refine_ls_abs_structure_Flack -2(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL 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 O(1) O 0.6048(6) -0.0786(4) 0.8685(3) 0.0317(10) Uani 1.00 1 d P . . O(2) O 1.1874(5) 0.1029(4) 1.1962(2) 0.0165(9) Uani 0.99 1 d P . . O(3) O 1.4085(5) 0.2375(4) 0.9876(3) 0.0264(10) Uani 0.99 1 d P . . O(4) O 0.9270(6) 0.5452(5) 1.3496(3) 0.0358(12) Uani 1.01 1 d P . . O(5) O 0.8854(5) 0.6184(4) 0.8646(3) 0.0276(9) Uani 1.03 1 d P . . O(6) O 0.3025(5) 0.4410(4) 0.5350(2) 0.0214(8) Uani 1.02 1 d P . . O(7) O 0.0855(5) 0.3070(5) 0.7437(3) 0.0301(11) Uani 1.03 1 d P . . O(8) O 0.5701(6) -0.0018(4) 0.3810(3) 0.0319(11) Uani 1.00 1 d P . . C(1) C 0.6775(6) -0.0552(6) 0.9738(4) 0.0148(10) Uani 0.92 1 d P . . C(2) C 0.5503(7) -0.1234(6) 1.0599(4) 0.0289(12) Uani 1.08 1 d P . . C(3) C 0.6641(7) -0.2228(5) 1.1300(3) 0.0241(11) Uani 1.01 1 d P . . C(4) C 0.8763(7) -0.1124(5) 1.2059(4) 0.0236(12) Uani 1.04 1 d P . . C(5) C 1.0097(7) -0.0346(6) 1.1248(4) 0.0098(11) Uani 0.79 1 d P . . C(6) C 0.9059(7) 0.0363(5) 1.0305(3) 0.0190(11) Uani 1.04 1 d P . . C(7) C 1.0511(7) 0.0485(6) 0.9395(3) 0.0180(12) Uani 0.93 1 d P . . C(8) C 1.2434(6) 0.1850(5) 1.0201(3) 0.0191(10) Uani 0.99 1 d P . . C(9) C 1.1893(6) 0.2377(5) 1.1408(3) 0.0143(10) Uani 0.94 1 d P . . C(10) C 0.9517(5) 0.2236(5) 1.0997(3) 0.0145(10) Uani 1.00 1 d P . . C(11) C 0.9336(7) 0.3485(5) 1.0237(4) 0.0202(11) Uani 1.03 1 d P . . C(12) C 1.0972(8) 0.5168(6) 1.0898(4) 0.0320(13) Uani 1.25 1 d P . . C(13) C 1.1771(7) 0.5197(5) 1.2245(3) 0.0128(10) Uani 0.90 1 d P . . C(14) C 1.3134(6) 0.4037(5) 1.2274(3) 0.0261(10) Uani 1.12 1 d P . . C(15) C 0.8704(7) 0.2764(5) 1.2145(3) 0.0158(10) Uani 0.96 1 d P . . C(16) C 0.9885(7) 0.4607(5) 1.2731(3) 0.0292(11) Uani 1.16 1 d P . . C(17) C 0.8159(7) 0.5979(5) 0.7553(4) 0.0263(11) Uani 1.10 1 d P . . C(18) C 0.9420(7) 0.6649(6) 0.6704(4) 0.0192(13) Uani 0.95 1 d P . . C(19) C 0.8311(7) 0.7608(5) 0.6017(4) 0.0244(12) Uani 1.02 1 d P . . C(20) C 0.6200(7) 0.6507(5) 0.5240(3) 0.0202(11) Uani 0.99 1 d P . . C(21) C 0.4862(6) 0.5787(5) 0.6030(3) 0.0297(10) Uani 1.24 1 d P . . C(22) C 0.5906(7) 0.5026(5) 0.7007(3) 0.0176(11) Uani 1.03 1 d P . . C(23) C 0.4385(7) 0.4948(5) 0.7913(3) 0.0256(11) Uani 1.11 1 d P . . C(24) C 0.2452(7) 0.3609(5) 0.7167(3) 0.0198(10) Uani 1.03 1 d P . . C(25) C 0.3057(7) 0.3042(5) 0.5910(4) 0.0218(11) Uani 1.11 1 d P . . C(26) C 0.5289(7) 0.3169(5) 0.6285(3) 0.0192(11) Uani 1.06 1 d P . . C(27) C 0.6207(6) 0.2616(5) 0.5160(3) 0.0231(11) Uani 1.07 1 d P . . C(28) C 0.5078(6) 0.0842(5) 0.4567(3) 0.0130(11) Uani 0.83 1 d P . . C(29) C 0.3147(6) 0.0195(4) 0.5073(3) 0.0299(10) Uani 1.17 1 d P . . C(30) C 0.3988(7) 0.0249(6) 0.6401(4) 0.0138(12) Uani 0.82 1 d P . . C(31) C 0.5571(7) 0.1943(5) 0.7066(3) 0.0185(11) Uani 0.99 1 d P . . C(32) C 0.1787(7) 0.1414(6) 0.5062(4) 0.0139(11) Uani 0.92 1 d P . . H(1) H 0.4118 -0.1963 1.0132 0.033 Uiso 1.00 1 c R . . H(2) H 0.5274 -0.0317 1.1189 0.033 Uiso 1.00 1 c R . . H(3) H 0.5767 -0.2692 1.1836 0.031 Uiso 1.00 1 c R . . H(4) H 0.6850 -0.3155 1.0710 0.031 Uiso 1.00 1 c R . . H(5) H 0.9483 -0.1785 1.2476 0.029 Uiso 1.00 1 c R . . H(6) H 0.8553 -0.0240 1.2689 0.029 Uiso 1.00 1 c R . . H(7) H 1.0656 -0.1214 1.0808 0.011 Uiso 1.00 1 c R . . H(8) H 1.0842 -0.0565 0.9119 0.025 Uiso 1.00 1 c R . . H(9) H 0.9903 0.0808 0.8678 0.024 Uiso 1.00 1 c R . . H(10) H 0.7901 0.3600 1.0133 0.023 Uiso 1.00 1 c R . . H(11) H 0.9614 0.3085 0.9421 0.022 Uiso 1.00 1 c R . . H(12) H 1.2152 0.5359 1.0474 0.037 Uiso 1.00 1 c R . . H(13) H 1.0300 0.6059 1.0878 0.037 Uiso 1.00 1 c R . . H(14) H 1.2584 0.6340 1.2721 0.014 Uiso 1.00 1 c R . . H(15) H 1.4448 0.4468 1.2009 0.028 Uiso 1.00 1 c R . . H(16) H 1.3493 0.3905 1.3108 0.027 Uiso 1.00 1 c R . . H(17) H 0.8957 0.2097 1.2721 0.018 Uiso 1.00 1 c R . . H(18) H 0.7180 0.2608 1.1926 0.017 Uiso 1.00 1 c R . . H(19) H 0.9661 0.5735 0.6117 0.022 Uiso 1.00 1 c R . . H(20) H 1.0797 0.7377 0.7183 0.022 Uiso 1.00 1 c R . . H(21) H 0.8089 0.8532 0.6603 0.025 Uiso 1.00 1 c R . . H(22) H 0.9189 0.8075 0.5484 0.025 Uiso 1.00 1 c R . . H(23) H 0.5478 0.7156 0.4810 0.023 Uiso 1.00 1 c R . . H(24) H 0.6427 0.5621 0.4621 0.023 Uiso 1.00 1 c R . . H(25) H 0.4328 0.6666 0.6477 0.034 Uiso 1.00 1 c R . . H(26) H 0.4977 0.4641 0.8642 0.027 Uiso 1.00 1 c R . . H(27) H 0.4077 0.6011 0.8171 0.027 Uiso 1.00 1 c R . . H(28) H 0.6005 0.3295 0.4584 0.031 Uiso 1.00 1 c R . . H(29) H 0.7723 0.2753 0.5399 0.031 Uiso 1.00 1 c R . . H(30) H 0.2333 -0.0947 0.4596 0.036 Uiso 1.00 1 c R . . H(31) H 0.2803 0.0061 0.6822 0.016 Uiso 1.00 1 c R . . H(32) H 0.4661 -0.0640 0.6427 0.017 Uiso 1.00 1 c R . . H(33) H 0.7009 0.1835 0.7154 0.024 Uiso 1.00 1 c R . . H(34) H 0.5315 0.2336 0.7889 0.024 Uiso 1.00 1 c R . . H(35) H 0.1422 0.1530 0.4224 0.018 Uiso 1.00 1 c R . . H(36) H 0.0475 0.0979 0.5327 0.018 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.033(2) 0.034(2) 0.0214(19) 0.0010(16) -0.0061(15) 0.0108(15) O(2) 0.0138(18) 0.0140(18) 0.0198(18) 0.0002(13) 0.0026(13) 0.0051(13) O(3) 0.020(2) 0.030(2) 0.026(2) 0.0025(16) 0.0103(15) 0.0054(15) O(4) 0.047(2) 0.028(2) 0.034(2) 0.0167(19) 0.0152(18) -0.0013(17) O(5) 0.0244(18) 0.028(2) 0.0255(18) 0.0030(15) 0.0004(13) 0.0041(14) O(6) 0.0234(19) 0.0204(17) 0.0203(17) 0.0073(13) -0.0004(12) 0.0073(12) O(7) 0.024(2) 0.039(2) 0.028(2) 0.0075(17) 0.0109(16) 0.0085(16) O(8) 0.035(2) 0.025(2) 0.035(2) 0.0059(17) 0.0204(17) -0.0001(15) C(1) 0.009(2) 0.010(2) 0.021(2) -0.0044(16) 0.0042(15) 0.0030(15) C(2) 0.022(2) 0.036(2) 0.024(2) 0.0052(19) -0.0012(18) 0.0071(18) C(3) 0.029(2) 0.021(2) 0.028(2) 0.0107(18) 0.0097(17) 0.0121(16) C(4) 0.023(2) 0.027(2) 0.022(2) 0.0072(19) 0.0053(18) 0.0103(17) C(5) 0.016(2) 0.003(2) 0.009(2) -0.0030(17) 0.0086(16) 0.0035(16) C(6) 0.016(2) 0.018(2) 0.023(2) 0.0048(17) 0.0044(16) 0.0052(15) C(7) 0.023(2) 0.022(2) 0.016(2) 0.0113(19) 0.0142(17) 0.0081(17) C(8) 0.018(2) 0.010(2) 0.032(2) 0.0044(15) 0.0059(15) 0.0101(15) C(9) 0.0176(19) 0.021(2) 0.008(2) 0.0094(16) 0.0054(14) 0.0054(16) C(10) 0.0124(17) 0.012(2) 0.0181(19) 0.0008(15) 0.0014(14) 0.0058(15) C(11) 0.018(2) 0.014(2) 0.024(2) -0.0009(17) 0.0004(17) 0.0031(17) C(12) 0.038(2) 0.025(2) 0.030(2) 0.0062(19) 0.005(2) 0.0060(18) C(13) 0.009(2) 0.017(2) 0.0085(17) 0.0004(16) 0.0001(14) 0.0008(13) C(14) 0.028(2) 0.018(2) 0.022(2) -0.0031(15) 0.0006(15) -0.0007(14) C(15) 0.022(2) 0.0080(18) 0.013(2) -0.0000(15) 0.0066(17) -0.0042(14) C(16) 0.032(2) 0.025(2) 0.0282(19) 0.0099(18) 0.0009(15) 0.0048(15) C(17) 0.034(2) 0.0217(19) 0.024(2) 0.0143(16) 0.0014(17) 0.0036(15) C(18) 0.016(2) 0.010(2) 0.028(2) -0.003(2) 0.012(2) 0.001(2) C(19) 0.023(2) 0.019(2) 0.021(2) -0.0091(18) 0.0048(18) -0.0003(17) C(20) 0.026(2) 0.012(2) 0.018(2) -0.0004(17) 0.0034(17) 0.0041(16) C(21) 0.023(2) 0.030(2) 0.032(2) 0.0074(16) -0.0026(15) 0.0055(15) C(22) 0.021(2) 0.018(2) 0.012(2) 0.0034(17) 0.0029(16) 0.0032(16) C(23) 0.025(2) 0.021(2) 0.023(2) 0.0005(17) -0.0008(16) -0.0019(15) C(24) 0.022(2) 0.030(2) 0.0097(16) 0.0112(17) 0.0065(14) 0.0022(12) C(25) 0.019(2) 0.015(2) 0.030(2) 0.0019(16) 0.0039(16) 0.0067(16) C(26) 0.019(2) 0.022(2) 0.015(2) 0.0055(17) 0.0061(17) 0.0006(15) C(27) 0.019(2) 0.030(2) 0.028(2) 0.0109(17) 0.0096(16) 0.0153(15) C(28) 0.017(2) 0.016(2) 0.008(2) 0.0076(17) 0.0065(16) 0.0033(17) C(29) 0.037(2) 0.016(2) 0.037(2) 0.0082(16) 0.0079(15) 0.0054(15) C(30) 0.012(2) 0.013(2) 0.016(2) 0.0020(18) 0.0022(17) 0.0066(18) C(31) 0.021(2) 0.024(2) 0.015(2) 0.0101(18) 0.0047(17) 0.0095(17) C(32) 0.010(2) 0.019(2) 0.017(2) 0.0080(18) 0.0032(16) 0.0076(17) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(1) 1.191(5) yes . . O(2) C(5) 1.459(4) yes . . O(2) C(9) 1.441(6) yes . . O(3) C(8) 1.236(5) yes . . O(4) C(16) 1.211(6) yes . . O(5) C(17) 1.234(5) yes . . O(6) C(21) 1.472(4) yes . . O(6) C(25) 1.466(6) yes . . O(7) C(24) 1.177(6) yes . . O(8) C(28) 1.216(6) yes . . C(1) C(2) 1.518(7) yes . . C(1) C(6) 1.521(5) yes . . C(2) C(3) 1.556(7) yes . . C(3) C(4) 1.528(5) yes . . C(4) C(5) 1.529(7) yes . . C(5) C(6) 1.522(7) yes . . C(6) C(7) 1.534(7) yes . . C(6) C(10) 1.583(6) yes . . C(7) C(8) 1.541(5) yes . . C(8) C(9) 1.492(6) yes . . C(9) C(10) 1.571(6) yes . . C(9) C(14) 1.525(5) yes . . C(10) C(11) 1.544(7) yes . . C(10) C(15) 1.526(6) yes . . C(11) C(12) 1.556(5) yes . . C(12) C(13) 1.555(6) yes . . C(13) C(14) 1.524(7) yes . . C(13) C(16) 1.481(6) yes . . C(15) C(16) 1.551(5) yes . . C(17) C(18) 1.498(7) yes . . C(17) C(22) 1.507(5) yes . . C(18) C(19) 1.513(8) yes . . C(19) C(20) 1.529(5) yes . . C(20) C(21) 1.492(6) yes . . C(21) C(22) 1.582(7) yes . . C(22) C(23) 1.563(7) yes . . C(22) C(26) 1.570(6) yes . . C(23) C(24) 1.514(5) yes . . C(24) C(25) 1.570(6) yes . . C(25) C(26) 1.474(7) yes . . C(25) C(32) 1.503(5) yes . . C(26) C(27) 1.550(6) yes . . C(26) C(31) 1.556(7) yes . . C(27) C(28) 1.497(5) yes . . C(28) C(29) 1.531(6) yes . . C(29) C(30) 1.534(6) yes . . C(29) C(32) 1.563(7) yes . . C(30) C(31) 1.549(5) yes . . C(2) H(1) 0.990(5) no . . C(2) H(2) 0.990(7) no . . C(3) H(3) 0.990(7) no . . C(3) H(4) 0.990(6) no . . C(4) H(5) 0.990(7) no . . C(4) H(6) 0.990(6) no . . C(5) H(7) 1.000 no . . C(7) H(8) 0.990(7) no . . C(7) H(9) 0.990(7) no . . C(11) H(10) 0.990(7) no . . C(11) H(11) 0.990(6) no . . C(12) H(12) 0.990(8) no . . C(12) H(13) 0.990(8) no . . C(13) H(14) 1.000 no . . C(14) H(15) 0.990(6) no . . C(14) H(16) 0.990(6) no . . C(15) H(17) 0.990(6) no . . C(15) H(18) 0.990(6) no . . C(18) H(19) 0.990(7) no . . C(18) H(20) 0.990(5) no . . C(19) H(21) 0.990(7) no . . C(19) H(22) 0.990(7) no . . C(20) H(23) 0.990(7) no . . C(20) H(24) 0.990(6) no . . C(21) H(25) 1.000 no . . C(23) H(26) 0.990(6) no . . C(23) H(27) 0.990(7) no . . C(27) H(28) 0.990(6) no . . C(27) H(29) 0.990(6) no . . C(29) H(30) 1.000 no . . C(30) H(31) 0.990(7) no . . C(30) H(32) 0.990(8) no . . C(31) H(33) 0.990(7) no . . C(31) H(34) 0.990(6) no . . C(32) H(35) 0.990(7) no . . C(32) H(36) 0.990(7) no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(5) O(2) C(9) 106.8(3) yes . . . C(21) O(6) C(25) 106.6(3) yes . . . O(1) C(1) C(2) 121.9(3) yes . . . O(1) C(1) C(6) 122.9(4) yes . . . C(2) C(1) C(6) 115.1(3) yes . . . C(1) C(2) C(3) 111.0(4) yes . . . C(2) C(3) C(4) 110.4(3) yes . . . C(3) C(4) C(5) 110.4(3) yes . . . O(2) C(5) C(4) 111.8(3) yes . . . O(2) C(5) C(6) 103.8(3) yes . . . C(4) C(5) C(6) 118.0(4) yes . . . C(1) C(6) C(5) 115.3(4) yes . . . C(1) C(6) C(7) 114.9(3) yes . . . C(1) C(6) C(10) 115.6(4) yes . . . C(5) C(6) C(7) 104.6(4) yes . . . C(5) C(6) C(10) 103.3(3) yes . . . C(7) C(6) C(10) 101.5(3) yes . . . C(6) C(7) C(8) 100.0(3) yes . . . O(3) C(8) C(7) 125.0(3) yes . . . O(3) C(8) C(9) 128.2(3) yes . . . C(7) C(8) C(9) 106.8(3) yes . . . O(2) C(9) C(8) 105.2(3) yes . . . O(2) C(9) C(10) 104.2(3) yes . . . O(2) C(9) C(14) 112.4(3) yes . . . C(8) C(9) C(10) 100.4(3) yes . . . C(8) C(9) C(14) 120.0(3) yes . . . C(10) C(9) C(14) 113.0(3) yes . . . C(6) C(10) C(9) 90.6(3) yes . . . C(6) C(10) C(11) 118.5(3) yes . . . C(6) C(10) C(15) 122.2(3) yes . . . C(9) C(10) C(11) 108.7(3) yes . . . C(9) C(10) C(15) 107.3(3) yes . . . C(11) C(10) C(15) 107.0(3) yes . . . C(10) C(11) C(12) 108.9(3) yes . . . C(11) C(12) C(13) 109.8(4) yes . . . C(12) C(13) C(14) 109.0(3) yes . . . C(12) C(13) C(16) 106.3(3) yes . . . C(14) C(13) C(16) 110.3(3) yes . . . C(9) C(14) C(13) 107.6(3) yes . . . C(10) C(15) C(16) 107.3(3) yes . . . O(4) C(16) C(13) 124.8(3) yes . . . O(4) C(16) C(15) 121.9(4) yes . . . C(13) C(16) C(15) 113.2(3) yes . . . O(5) C(17) C(18) 123.9(3) yes . . . O(5) C(17) C(22) 119.7(4) yes . . . C(18) C(17) C(22) 116.3(3) yes . . . C(17) C(18) C(19) 110.8(4) yes . . . C(18) C(19) C(20) 111.0(3) yes . . . C(19) C(20) C(21) 109.9(3) yes . . . O(6) C(21) C(20) 113.7(3) yes . . . O(6) C(21) C(22) 102.4(3) yes . . . C(20) C(21) C(22) 117.3(4) yes . . . C(17) C(22) C(21) 112.5(3) yes . . . C(17) C(22) C(23) 116.1(3) yes . . . C(17) C(22) C(26) 121.0(4) yes . . . C(21) C(22) C(23) 103.0(4) yes . . . C(21) C(22) C(26) 100.9(3) yes . . . C(23) C(22) C(26) 100.8(3) yes . . . C(22) C(23) C(24) 102.7(3) yes . . . O(7) C(24) C(23) 129.7(3) yes . . . O(7) C(24) C(25) 126.4(3) yes . . . C(23) C(24) C(25) 103.9(3) yes . . . O(6) C(25) C(24) 103.6(3) yes . . . O(6) C(25) C(26) 105.3(3) yes . . . O(6) C(25) C(32) 111.8(3) yes . . . C(24) C(25) C(26) 101.9(3) yes . . . C(24) C(25) C(32) 118.8(4) yes . . . C(26) C(25) C(32) 113.9(4) yes . . . C(22) C(26) C(25) 94.4(3) yes . . . C(22) C(26) C(27) 121.2(3) yes . . . C(22) C(26) C(31) 115.5(3) yes . . . C(25) C(26) C(27) 110.5(3) yes . . . C(25) C(26) C(31) 110.8(3) yes . . . C(27) C(26) C(31) 104.1(4) yes . . . C(26) C(27) C(28) 108.2(3) yes . . . O(8) C(28) C(27) 123.2(4) yes . . . O(8) C(28) C(29) 123.5(3) yes . . . C(27) C(28) C(29) 113.2(3) yes . . . C(28) C(29) C(30) 105.5(3) yes . . . C(28) C(29) C(32) 108.3(3) yes . . . C(30) C(29) C(32) 108.6(3) yes . . . C(29) C(30) C(31) 110.8(4) yes . . . C(26) C(31) C(30) 107.6(3) yes . . . C(25) C(32) C(29) 107.6(3) yes . . . C(1) C(2) H(1) 109.7(5) no . . . C(1) C(2) H(2) 109.5(5) no . . . C(3) C(2) H(1) 109.1(5) no . . . C(3) C(2) H(2) 109.4(5) no . . . H(1) C(2) H(2) 108.0(6) no . . . C(2) C(3) H(3) 109.7(5) no . . . C(2) C(3) H(4) 109.4(4) no . . . C(4) C(3) H(3) 109.9(4) no . . . C(4) C(3) H(4) 109.3(5) no . . . H(3) C(3) H(4) 108.0(5) no . . . C(3) C(4) H(5) 109.3(4) no . . . C(3) C(4) H(6) 109.5(5) no . . . C(5) C(4) H(5) 110.3(5) no . . . C(5) C(4) H(6) 109.1(5) no . . . H(5) C(4) H(6) 108.2(5) no . . . O(2) C(5) H(7) 107.9 no . . . C(4) C(5) H(7) 107.1 no . . . C(6) C(5) H(7) 107.8 no . . . C(6) C(7) H(8) 111.4(5) no . . . C(6) C(7) H(9) 111.9(5) no . . . C(8) C(7) H(8) 111.9(5) no . . . C(8) C(7) H(9) 112.0(5) no . . . H(8) C(7) H(9) 109.4(5) no . . . C(10) C(11) H(10) 109.6(5) no . . . C(10) C(11) H(11) 109.7(5) no . . . C(12) C(11) H(10) 110.7(5) no . . . C(12) C(11) H(11) 109.4(5) no . . . H(10) C(11) H(11) 108.4(5) no . . . C(11) C(12) H(12) 110.2(4) no . . . C(11) C(12) H(13) 109.0(5) no . . . C(13) C(12) H(12) 110.5(5) no . . . C(13) C(12) H(13) 109.3(5) no . . . H(12) C(12) H(13) 108.0(6) no . . . C(12) C(13) H(14) 110.4 no . . . C(14) C(13) H(14) 110.4 no . . . C(16) C(13) H(14) 110.5 no . . . C(9) C(14) H(15) 109.6(4) no . . . C(9) C(14) H(16) 109.8(4) no . . . C(13) C(14) H(15) 110.7(5) no . . . C(13) C(14) H(16) 110.6(4) no . . . H(15) C(14) H(16) 108.5(5) no . . . C(10) C(15) H(17) 110.6(5) no . . . C(10) C(15) H(18) 109.6(4) no . . . C(16) C(15) H(17) 110.2(3) no . . . C(16) C(15) H(18) 110.6(4) no . . . H(17) C(15) H(18) 108.5(5) no . . . C(17) C(18) H(19) 109.9(5) no . . . C(17) C(18) H(20) 108.9(5) no . . . C(19) C(18) H(19) 109.4(5) no . . . C(19) C(18) H(20) 109.6(5) no . . . H(19) C(18) H(20) 108.1(6) no . . . C(18) C(19) H(21) 109.4(5) no . . . C(18) C(19) H(22) 109.7(5) no . . . C(20) C(19) H(21) 109.4(5) no . . . C(20) C(19) H(22) 109.2(4) no . . . H(21) C(19) H(22) 108.1(6) no . . . C(19) C(20) H(23) 110.1(4) no . . . C(19) C(20) H(24) 109.4(5) no . . . C(21) C(20) H(23) 109.0(5) no . . . C(21) C(20) H(24) 110.2(4) no . . . H(23) C(20) H(24) 108.1(5) no . . . O(6) C(21) H(25) 107.1 no . . . C(20) C(21) H(25) 108.2 no . . . C(22) C(21) H(25) 107.5 no . . . C(22) C(23) H(26) 110.9(5) no . . . C(22) C(23) H(27) 111.5(5) no . . . C(24) C(23) H(26) 111.0(4) no . . . C(24) C(23) H(27) 111.4(5) no . . . H(26) C(23) H(27) 109.2(5) no . . . C(26) C(27) H(28) 109.3(5) no . . . C(26) C(27) H(29) 111.1(4) no . . . C(28) C(27) H(28) 110.1(3) no . . . C(28) C(27) H(29) 109.8(5) no . . . H(28) C(27) H(29) 108.4(5) no . . . C(28) C(29) H(30) 111.3 no . . . C(30) C(29) H(30) 111.4 no . . . C(32) C(29) H(30) 111.5 no . . . C(29) C(30) H(31) 108.9(4) no . . . C(29) C(30) H(32) 109.7(4) no . . . C(31) C(30) H(31) 109.0(4) no . . . C(31) C(30) H(32) 110.1(4) no . . . H(31) C(30) H(32) 108.2(6) no . . . C(26) C(31) H(33) 110.7(5) no . . . C(26) C(31) H(34) 110.3(5) no . . . C(30) C(31) H(33) 109.4(5) no . . . C(30) C(31) H(34) 110.5(4) no . . . H(33) C(31) H(34) 108.3(5) no . . . C(25) C(32) H(35) 110.5(5) no . . . C(25) C(32) H(36) 111.0(5) no . . . C(29) C(32) H(35) 109.6(5) no . . . C(29) C(32) H(36) 109.8(5) no . . . H(35) C(32) H(36) 108.4(5) no . . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(5) O(2) C(9) C(8) -67.9(4) ? . . . . C(5) O(2) C(9) C(10) 37.2(4) ? . . . . C(5) O(2) C(9) C(14) 159.9(3) ? . . . . C(9) O(2) C(5) C(4) -131.4(4) ? . . . . C(9) O(2) C(5) C(6) -3.1(4) ? . . . . C(21) O(6) C(25) C(24) 71.7(4) ? . . . . C(21) O(6) C(25) C(26) -35.0(4) ? . . . . C(21) O(6) C(25) C(32) -159.2(4) ? . . . . C(25) O(6) C(21) C(20) 128.1(4) ? . . . . C(25) O(6) C(21) C(22) 0.5(4) ? . . . . O(1) C(1) C(2) C(3) 126.9(5) ? . . . . O(1) C(1) C(6) C(5) -140.2(5) ? . . . . O(1) C(1) C(6) C(7) -18.5(7) ? . . . . O(1) C(1) C(6) C(10) 99.3(5) ? . . . . C(2) C(1) C(6) C(5) 36.5(6) ? . . . . C(2) C(1) C(6) C(7) 158.2(4) ? . . . . C(2) C(1) C(6) C(10) -84.0(5) ? . . . . C(6) C(1) C(2) C(3) -49.8(5) ? . . . . C(1) C(2) C(3) C(4) 60.6(4) ? . . . . C(2) C(3) C(4) C(5) -56.7(5) ? . . . . C(3) C(4) C(5) O(2) 164.8(4) ? . . . . C(3) C(4) C(5) C(6) 44.5(5) ? . . . . O(2) C(5) C(6) C(1) -158.6(3) ? . . . . O(2) C(5) C(6) C(7) 74.3(4) ? . . . . O(2) C(5) C(6) C(10) -31.5(4) ? . . . . C(4) C(5) C(6) C(1) -34.2(5) ? . . . . C(4) C(5) C(6) C(7) -161.3(3) ? . . . . C(4) C(5) C(6) C(10) 92.8(4) ? . . . . C(1) C(6) C(7) C(8) 164.5(4) ? . . . . C(1) C(6) C(10) C(9) 176.0(4) ? . . . . C(1) C(6) C(10) C(11) -72.3(5) ? . . . . C(1) C(6) C(10) C(15) 64.9(5) ? . . . . C(5) C(6) C(7) C(8) -68.2(4) ? . . . . C(5) C(6) C(10) C(9) 49.2(4) ? . . . . C(5) C(6) C(10) C(11) 160.9(3) ? . . . . C(5) C(6) C(10) C(15) -61.9(5) ? . . . . C(7) C(6) C(10) C(9) -59.0(3) ? . . . . C(7) C(6) C(10) C(11) 52.7(4) ? . . . . C(7) C(6) C(10) C(15) -170.1(3) ? . . . . C(10) C(6) C(7) C(8) 39.0(4) ? . . . . C(6) C(7) C(8) O(3) 178.3(5) ? . . . . C(6) C(7) C(8) C(9) -1.7(5) ? . . . . O(3) C(8) C(9) O(2) -108.5(5) ? . . . . O(3) C(8) C(9) C(10) 143.6(5) ? . . . . O(3) C(8) C(9) C(14) 19.3(8) ? . . . . C(7) C(8) C(9) O(2) 71.5(4) ? . . . . C(7) C(8) C(9) C(10) -36.4(4) ? . . . . C(7) C(8) C(9) C(14) -160.7(4) ? . . . . O(2) C(9) C(10) C(6) -52.1(3) ? . . . . O(2) C(9) C(10) C(11) -172.6(3) ? . . . . O(2) C(9) C(10) C(15) 72.0(4) ? . . . . O(2) C(9) C(14) C(13) -130.4(4) ? . . . . C(8) C(9) C(10) C(6) 56.6(3) ? . . . . C(8) C(9) C(10) C(11) -63.9(4) ? . . . . C(8) C(9) C(10) C(15) -179.2(3) ? . . . . C(8) C(9) C(14) C(13) 105.2(4) ? . . . . C(10) C(9) C(14) C(13) -12.8(5) ? . . . . C(14) C(9) C(10) C(6) -174.4(3) ? . . . . C(14) C(9) C(10) C(11) 65.1(4) ? . . . . C(14) C(9) C(10) C(15) -50.2(5) ? . . . . C(6) C(10) C(11) C(12) -147.0(4) ? . . . . C(6) C(10) C(15) C(16) 166.5(3) ? . . . . C(9) C(10) C(11) C(12) -45.6(5) ? . . . . C(9) C(10) C(15) C(16) 64.3(4) ? . . . . C(11) C(10) C(15) C(16) -52.1(4) ? . . . . C(15) C(10) C(11) C(12) 70.0(4) ? . . . . C(10) C(11) C(12) C(13) -16.5(5) ? . . . . C(11) C(12) C(13) C(14) 70.5(5) ? . . . . C(11) C(12) C(13) C(16) -48.3(5) ? . . . . C(12) C(13) C(14) C(9) -51.8(4) ? . . . . C(12) C(13) C(16) O(4) -111.2(5) ? . . . . C(12) C(13) C(16) C(15) 67.8(5) ? . . . . C(14) C(13) C(16) O(4) 130.8(5) ? . . . . C(14) C(13) C(16) C(15) -50.2(4) ? . . . . C(16) C(13) C(14) C(9) 64.5(4) ? . . . . C(10) C(15) C(16) O(4) 163.9(4) ? . . . . C(10) C(15) C(16) C(13) -15.2(5) ? . . . . O(5) C(17) C(18) C(19) -127.8(5) ? . . . . O(5) C(17) C(22) C(21) 141.5(4) ? . . . . O(5) C(17) C(22) C(23) 23.2(7) ? . . . . O(5) C(17) C(22) C(26) -99.4(5) ? . . . . C(18) C(17) C(22) C(21) -37.7(5) ? . . . . C(18) C(17) C(22) C(23) -156.0(4) ? . . . . C(18) C(17) C(22) C(26) 81.5(5) ? . . . . C(22) C(17) C(18) C(19) 51.3(5) ? . . . . C(17) C(18) C(19) C(20) -61.2(4) ? . . . . C(18) C(19) C(20) C(21) 58.6(5) ? . . . . C(19) C(20) C(21) O(6) -165.9(4) ? . . . . C(19) C(20) C(21) C(22) -46.4(5) ? . . . . O(6) C(21) C(22) C(17) 161.5(3) ? . . . . O(6) C(21) C(22) C(23) -72.8(3) ? . . . . O(6) C(21) C(22) C(26) 31.1(4) ? . . . . C(20) C(21) C(22) C(17) 36.2(5) ? . . . . C(20) C(21) C(22) C(23) 161.9(3) ? . . . . C(20) C(21) C(22) C(26) -94.1(4) ? . . . . C(17) C(22) C(23) C(24) -166.9(4) ? . . . . C(17) C(22) C(26) C(25) -174.5(4) ? . . . . C(17) C(22) C(26) C(27) -57.2(6) ? . . . . C(17) C(22) C(26) C(31) 70.0(5) ? . . . . C(21) C(22) C(23) C(24) 69.7(4) ? . . . . C(21) C(22) C(26) C(25) -49.7(4) ? . . . . C(21) C(22) C(26) C(27) 67.6(5) ? . . . . C(21) C(22) C(26) C(31) -165.3(3) ? . . . . C(23) C(22) C(26) C(25) 55.9(4) ? . . . . C(23) C(22) C(26) C(27) 173.2(4) ? . . . . C(23) C(22) C(26) C(31) -59.7(5) ? . . . . C(26) C(22) C(23) C(24) -34.2(4) ? . . . . C(22) C(23) C(24) O(7) 179.3(5) ? . . . . C(22) C(23) C(24) C(25) 0.4(5) ? . . . . O(7) C(24) C(25) O(6) 108.0(5) ? . . . . O(7) C(24) C(25) C(26) -142.8(5) ? . . . . O(7) C(24) C(25) C(32) -16.6(8) ? . . . . C(23) C(24) C(25) O(6) -72.9(4) ? . . . . C(23) C(24) C(25) C(26) 36.3(4) ? . . . . C(23) C(24) C(25) C(32) 162.4(4) ? . . . . O(6) C(25) C(26) C(22) 52.2(3) ? . . . . O(6) C(25) C(26) C(27) -73.4(4) ? . . . . O(6) C(25) C(26) C(31) 171.7(3) ? . . . . O(6) C(25) C(32) C(29) 132.2(4) ? . . . . C(24) C(25) C(26) C(22) -55.6(4) ? . . . . C(24) C(25) C(26) C(27) 178.7(3) ? . . . . C(24) C(25) C(26) C(31) 63.8(4) ? . . . . C(24) C(25) C(32) C(29) -107.3(5) ? . . . . C(26) C(25) C(32) C(29) 12.9(5) ? . . . . C(32) C(25) C(26) C(22) 175.1(4) ? . . . . C(32) C(25) C(26) C(27) 49.4(5) ? . . . . C(32) C(25) C(26) C(31) -65.4(5) ? . . . . C(22) C(26) C(27) C(28) -171.4(4) ? . . . . C(22) C(26) C(31) C(30) 153.0(4) ? . . . . C(25) C(26) C(27) C(28) -62.5(5) ? . . . . C(25) C(26) C(31) C(30) 47.2(5) ? . . . . C(27) C(26) C(31) C(30) -71.7(4) ? . . . . C(31) C(26) C(27) C(28) 56.5(4) ? . . . . C(26) C(27) C(28) O(8) -165.6(4) ? . . . . C(26) C(27) C(28) C(29) 10.5(5) ? . . . . O(8) C(28) C(29) C(30) 110.3(5) ? . . . . O(8) C(28) C(29) C(32) -133.6(4) ? . . . . C(27) C(28) C(29) C(30) -65.7(5) ? . . . . C(27) C(28) C(29) C(32) 50.4(4) ? . . . . C(28) C(29) C(30) C(31) 48.7(5) ? . . . . C(28) C(29) C(32) C(25) -63.4(4) ? . . . . C(30) C(29) C(32) C(25) 50.7(4) ? . . . . C(32) C(29) C(30) C(31) -67.3(4) ? . . . . C(29) C(30) C(31) C(26) 16.1(5) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(3) 3.448(6) ? . 1_455 O(1) O(5) 3.596(6) ? . 1_545 O(1) C(17) 3.546(6) ? . 1_545 O(1) C(23) 3.467(5) ? . 1_545 O(1) C(30) 3.189(6) ? . . O(1) C(31) 3.350(6) ? . . O(2) O(8) 3.518(5) ? . 1_656 O(2) C(28) 3.486(5) ? . 1_656 O(2) C(32) 3.516(5) ? . 1_656 O(3) O(1) 3.448(6) ? . 1_655 O(3) O(7) 3.541(5) ? . 1_655 O(3) C(1) 3.458(7) ? . 1_655 O(3) C(11) 3.371(6) ? . 1_655 O(3) C(23) 3.482(6) ? . 1_655 O(3) C(31) 3.489(6) ? . 1_655 O(4) O(6) 3.485(5) ? . 1_656 O(4) C(18) 3.591(6) ? . 1_556 O(4) C(19) 3.342(6) ? . 1_556 O(4) C(20) 3.242(6) ? . 1_556 O(5) O(1) 3.596(6) ? . 1_565 O(5) O(7) 3.438(6) ? . 1_655 O(5) C(1) 3.541(6) ? . 1_565 O(5) C(5) 3.597(5) ? . 1_565 O(5) C(7) 3.496(6) ? . 1_565 O(5) C(11) 3.305(7) ? . . O(5) C(12) 3.165(6) ? . . O(6) O(4) 3.485(5) ? . 1_454 O(6) C(14) 3.491(5) ? . 1_454 O(6) C(16) 3.480(5) ? . 1_454 O(7) O(3) 3.541(5) ? . 1_455 O(7) O(5) 3.438(6) ? . 1_455 O(7) C(7) 3.485(6) ? . 1_455 O(7) C(11) 3.488(6) ? . 1_455 O(7) C(17) 3.449(6) ? . 1_455 O(7) C(31) 3.392(6) ? . 1_455 O(8) O(2) 3.518(5) ? . 1_454 O(8) C(2) 3.589(6) ? . 1_554 O(8) C(3) 3.346(6) ? . 1_554 O(8) C(4) 3.256(6) ? . 1_554 C(1) O(3) 3.458(7) ? . 1_455 C(1) O(5) 3.541(6) ? . 1_545 C(2) O(8) 3.589(6) ? . 1_556 C(3) O(8) 3.346(6) ? . 1_556 C(4) O(8) 3.256(6) ? . 1_556 C(5) O(5) 3.597(5) ? . 1_545 C(7) O(5) 3.496(6) ? . 1_545 C(7) O(7) 3.485(6) ? . 1_655 C(11) O(3) 3.371(6) ? . 1_455 C(11) O(5) 3.305(7) ? . . C(11) O(7) 3.488(6) ? . 1_655 C(12) O(5) 3.165(6) ? . . C(14) O(6) 3.491(5) ? . 1_656 C(16) O(6) 3.480(5) ? . 1_656 C(17) O(1) 3.546(6) ? . 1_565 C(17) O(7) 3.449(6) ? . 1_655 C(18) O(4) 3.591(6) ? . 1_554 C(19) O(4) 3.342(6) ? . 1_554 C(20) O(4) 3.242(6) ? . 1_554 C(23) O(1) 3.467(5) ? . 1_565 C(23) O(3) 3.482(6) ? . 1_455 C(28) O(2) 3.486(5) ? . 1_454 C(30) O(1) 3.189(6) ? . . C(31) O(1) 3.350(6) ? . . C(31) O(3) 3.489(6) ? . 1_455 C(31) O(7) 3.392(6) ? . 1_655 C(32) O(2) 3.516(5) ? . 1_454 O(1) H(20) 3.514(5) ? . 1_445 O(1) H(21) 2.954(6) ? . 1_545 O(1) H(25) 2.862 ? . 1_545 O(1) H(27) 2.663(5) ? . 1_545 O(1) H(31) 3.163(6) ? . . O(1) H(32) 2.667(6) ? . . O(1) H(33) 3.157(6) ? . . O(1) H(34) 3.160(7) ? . . O(2) H(2) 2.982(6) ? . 1_655 O(2) H(18) 3.511(5) ? . 1_655 O(2) H(35) 2.618(5) ? . 1_656 O(3) H(2) 3.228(7) ? . 1_655 O(3) H(10) 2.478(6) ? . 1_655 O(3) H(18) 2.848(5) ? . 1_655 O(3) H(26) 2.658(6) ? . 1_655 O(3) H(31) 3.519(5) ? . 1_655 O(3) H(34) 2.535(6) ? . 1_655 O(4) H(5) 2.862(7) ? . 1_565 O(4) H(15) 3.260(5) ? . 1_455 O(4) H(19) 2.936(6) ? . 1_556 O(4) H(22) 2.882(6) ? . 1_556 O(4) H(24) 2.479(6) ? . 1_556 O(4) H(28) 3.108(6) ? . 1_556 O(4) H(29) 3.599(6) ? . 1_556 O(4) H(30) 3.164 ? . 1_666 O(5) H(1) 3.518(5) ? . 1_665 O(5) H(4) 2.918(6) ? . 1_565 O(5) H(7) 2.855 ? . 1_565 O(5) H(8) 2.706(6) ? . 1_565 O(5) H(10) 3.092(6) ? . . O(5) H(11) 3.136(7) ? . . O(5) H(12) 3.151(6) ? . . O(5) H(13) 2.641(6) ? . . O(6) H(16) 2.598(5) ? . 1_454 O(6) H(19) 2.948(6) ? . 1_455 O(6) H(29) 3.523(5) ? . 1_455 O(7) H(9) 2.666(6) ? . 1_455 O(7) H(11) 2.537(6) ? . 1_455 O(7) H(12) 3.495(5) ? . 1_455 O(7) H(19) 3.215(7) ? . 1_455 O(7) H(29) 2.833(5) ? . 1_455 O(7) H(33) 2.494(5) ? . 1_455 O(8) H(2) 2.932(6) ? . 1_554 O(8) H(3) 2.897(5) ? . 1_554 O(8) H(6) 2.489(6) ? . 1_554 O(8) H(14) 3.203 ? . 1_444 O(8) H(17) 3.085(6) ? . 1_554 O(8) H(18) 3.526(6) ? . 1_554 O(8) H(23) 2.898(6) ? . 1_545 O(8) H(36) 3.243(5) ? . 1_655 C(1) H(27) 3.091(5) ? . 1_545 C(2) H(7) 3.317 ? . 1_455 C(2) H(8) 3.588(7) ? . 1_455 C(2) H(12) 3.208(6) ? . 1_445 C(2) H(27) 3.114(5) ? . 1_545 C(3) H(12) 3.107(6) ? . 1_445 C(3) H(13) 3.225(8) ? . 1_545 C(3) H(14) 3.488 ? . 1_445 C(3) H(15) 3.210(6) ? . 1_445 C(3) H(26) 3.460(5) ? . 1_545 C(3) H(27) 3.580(5) ? . 1_545 C(4) H(13) 3.027(7) ? . 1_545 C(4) H(30) 3.451 ? . 1_656 C(4) H(35) 2.993(5) ? . 1_656 C(5) H(2) 3.497(7) ? . 1_655 C(5) H(13) 3.098(7) ? . 1_545 C(5) H(35) 3.344(6) ? . 1_656 C(7) H(20) 3.359(6) ? . 1_545 C(7) H(21) 3.263(5) ? . 1_545 C(7) H(31) 3.522(7) ? . 1_655 C(8) H(2) 3.246(7) ? . 1_655 C(8) H(18) 3.344(6) ? . 1_655 C(8) H(26) 3.559(6) ? . 1_655 C(8) H(34) 3.545(6) ? . 1_655 C(9) H(18) 3.478(6) ? . 1_655 C(9) H(35) 3.504(7) ? . 1_656 C(11) H(33) 3.492(5) ? . . C(11) H(34) 3.322(6) ? . . C(12) H(1) 3.213(7) ? . 1_665 C(12) H(3) 3.201(6) ? . 1_665 C(12) H(4) 3.443(8) ? . 1_565 C(12) H(5) 3.332(7) ? . 1_565 C(12) H(7) 3.220 ? . 1_565 C(13) H(3) 3.022(6) ? . 1_665 C(13) H(5) 3.337(7) ? . 1_565 C(13) H(23) 3.388(5) ? . 1_656 C(14) H(3) 3.135(6) ? . 1_665 C(14) H(18) 3.306(7) ? . 1_655 C(14) H(23) 3.397(5) ? . 1_656 C(14) H(24) 3.047(5) ? . 1_656 C(14) H(28) 3.323(6) ? . 1_656 C(14) H(35) 3.554(7) ? . 1_656 C(15) H(15) 3.538(7) ? . 1_455 C(15) H(28) 3.567(6) ? . 1_556 C(15) H(35) 3.315(7) ? . 1_656 C(16) H(5) 3.277(7) ? . 1_565 C(16) H(24) 3.550(6) ? . 1_556 C(17) H(8) 3.100(5) ? . 1_565 C(18) H(8) 3.118(6) ? . 1_565 C(18) H(25) 3.355 ? . 1_655 C(18) H(27) 3.568(7) ? . 1_655 C(18) H(31) 3.223(6) ? . 1_665 C(19) H(8) 3.557(5) ? . 1_565 C(19) H(9) 3.494(5) ? . 1_565 C(19) H(30) 3.472 ? . 1_665 C(19) H(31) 3.121(6) ? . 1_665 C(19) H(32) 3.237(7) ? . 1_565 C(19) H(36) 3.241(7) ? . 1_665 C(20) H(14) 3.455 ? . 1_454 C(20) H(16) 2.961(4) ? . 1_454 C(20) H(32) 3.054(7) ? . 1_565 C(21) H(16) 3.292(5) ? . 1_454 C(21) H(19) 3.514(7) ? . 1_455 C(21) H(32) 3.077(7) ? . 1_565 C(23) H(1) 3.348(6) ? . 1_565 C(23) H(4) 3.267(5) ? . 1_565 C(23) H(12) 3.486(7) ? . 1_455 C(24) H(9) 3.527(6) ? . 1_455 C(24) H(11) 3.475(7) ? . 1_455 C(24) H(19) 3.224(8) ? . 1_455 C(24) H(29) 3.341(6) ? . 1_455 C(25) H(16) 3.489(6) ? . 1_454 C(25) H(29) 3.498(7) ? . 1_455 C(27) H(16) 3.321(6) ? . 1_454 C(27) H(17) 3.588(6) ? . 1_554 C(27) H(36) 3.510(7) ? . 1_655 C(28) H(6) 3.568(7) ? . 1_554 C(28) H(23) 3.340(7) ? . 1_545 C(28) H(36) 3.585(6) ? . 1_655 C(29) H(5) 3.401(5) ? . 1_454 C(29) H(22) 3.006(6) ? . 1_445 C(29) H(23) 3.372(7) ? . 1_545 C(30) H(20) 3.240(7) ? . 1_445 C(30) H(21) 3.453(7) ? . 1_545 C(30) H(22) 3.210(6) ? . 1_445 C(30) H(23) 3.370(7) ? . 1_545 C(30) H(25) 3.191 ? . 1_545 C(31) H(10) 3.478(5) ? . . C(31) H(11) 3.337(6) ? . . C(32) H(5) 3.465(5) ? . 1_454 C(32) H(6) 3.055(5) ? . 1_454 C(32) H(16) 3.547(7) ? . 1_454 C(32) H(17) 3.311(7) ? . 1_454 C(32) H(22) 3.165(7) ? . 1_445 C(32) H(29) 3.273(7) ? . 1_455 H(1) O(5) 3.518(5) ? . 1_445 H(1) C(12) 3.213(7) ? . 1_445 H(1) C(23) 3.348(6) ? . 1_545 H(1) H(7) 2.747 ? . 1_455 H(1) H(8) 2.980(7) ? . 1_455 H(1) H(12) 2.514(7) ? . 1_445 H(1) H(13) 3.063(7) ? . 1_445 H(1) H(26) 3.311(7) ? . 1_545 H(1) H(27) 2.540(6) ? . 1_545 H(2) O(2) 2.982(6) ? . 1_455 H(2) O(3) 3.228(7) ? . 1_455 H(2) O(8) 2.932(6) ? . 1_556 H(2) C(5) 3.497(7) ? . 1_455 H(2) C(8) 3.246(7) ? . 1_455 H(2) H(7) 2.961 ? . 1_455 H(2) H(8) 3.470(6) ? . 1_455 H(3) O(8) 2.897(5) ? . 1_556 H(3) C(12) 3.201(6) ? . 1_445 H(3) C(13) 3.022(6) ? . 1_445 H(3) C(14) 3.135(6) ? . 1_445 H(3) H(12) 2.645(5) ? . 1_445 H(3) H(13) 3.511(6) ? . 1_445 H(3) H(14) 2.540 ? . 1_445 H(3) H(15) 2.465(6) ? . 1_445 H(3) H(23) 3.477(6) ? . 1_546 H(4) O(5) 2.918(6) ? . 1_545 H(4) C(12) 3.443(8) ? . 1_545 H(4) C(23) 3.267(5) ? . 1_545 H(4) H(10) 3.034(7) ? . 1_545 H(4) H(12) 3.060(7) ? . 1_445 H(4) H(13) 2.575(8) ? . 1_545 H(4) H(15) 3.073(6) ? . 1_445 H(4) H(26) 2.631(5) ? . 1_545 H(4) H(27) 3.064(6) ? . 1_545 H(5) O(4) 2.862(7) ? . 1_545 H(5) C(12) 3.332(7) ? . 1_545 H(5) C(13) 3.337(7) ? . 1_545 H(5) C(16) 3.277(7) ? . 1_545 H(5) C(29) 3.401(5) ? . 1_656 H(5) C(32) 3.465(5) ? . 1_656 H(5) H(13) 2.556(7) ? . 1_545 H(5) H(14) 2.968 ? . 1_545 H(5) H(22) 3.514(7) ? . 1_546 H(5) H(30) 2.713 ? . 1_656 H(5) H(35) 2.994(5) ? . 1_656 H(5) H(36) 3.492(6) ? . 1_656 H(6) O(8) 2.489(6) ? . 1_556 H(6) C(28) 3.568(7) ? . 1_556 H(6) C(32) 3.055(5) ? . 1_656 H(6) H(30) 3.375 ? . 1_656 H(6) H(35) 2.370(5) ? . 1_656 H(6) H(36) 2.970(6) ? . 1_656 H(7) O(5) 2.855 ? . 1_545 H(7) C(2) 3.317 ? . 1_655 H(7) C(12) 3.220 ? . 1_545 H(7) H(1) 2.747 ? . 1_655 H(7) H(2) 2.961 ? . 1_655 H(7) H(12) 3.335 ? . 1_545 H(7) H(13) 2.338 ? . 1_545 H(8) O(5) 2.706(6) ? . 1_545 H(8) C(2) 3.588(7) ? . 1_655 H(8) C(17) 3.100(5) ? . 1_545 H(8) C(18) 3.118(6) ? . 1_545 H(8) C(19) 3.557(5) ? . 1_545 H(8) H(1) 2.980(7) ? . 1_655 H(8) H(2) 3.470(6) ? . 1_655 H(8) H(20) 2.533(6) ? . 1_545 H(8) H(21) 3.031(6) ? . 1_545 H(8) H(31) 3.203(7) ? . 1_655 H(9) O(7) 2.666(6) ? . 1_655 H(9) C(19) 3.494(5) ? . 1_545 H(9) C(24) 3.527(6) ? . 1_655 H(9) H(20) 3.348(7) ? . 1_545 H(9) H(21) 2.656(5) ? . 1_545 H(9) H(31) 3.169(7) ? . 1_655 H(9) H(33) 2.863(7) ? . . H(10) O(3) 2.478(6) ? . 1_455 H(10) O(5) 3.092(6) ? . . H(10) C(31) 3.478(5) ? . . H(10) H(4) 3.034(7) ? . 1_565 H(10) H(15) 3.504(7) ? . 1_455 H(10) H(26) 2.861(7) ? . . H(10) H(33) 3.340(6) ? . . H(10) H(34) 2.729(5) ? . . H(11) O(5) 3.136(7) ? . . H(11) O(7) 2.537(6) ? . 1_655 H(11) C(24) 3.475(7) ? . 1_655 H(11) C(31) 3.337(6) ? . . H(11) H(33) 2.755(5) ? . . H(11) H(34) 3.006(6) ? . . H(12) O(5) 3.151(6) ? . . H(12) O(7) 3.495(5) ? . 1_655 H(12) C(2) 3.208(6) ? . 1_665 H(12) C(3) 3.107(6) ? . 1_665 H(12) C(23) 3.486(7) ? . 1_655 H(12) H(1) 2.514(7) ? . 1_665 H(12) H(3) 2.645(5) ? . 1_665 H(12) H(4) 3.060(7) ? . 1_665 H(12) H(7) 3.335 ? . 1_565 H(12) H(26) 3.106(7) ? . 1_655 H(12) H(27) 3.202(7) ? . 1_655 H(13) O(5) 2.641(6) ? . . H(13) C(3) 3.225(8) ? . 1_565 H(13) C(4) 3.027(7) ? . 1_565 H(13) C(5) 3.098(7) ? . 1_565 H(13) H(1) 3.063(7) ? . 1_665 H(13) H(3) 3.511(6) ? . 1_665 H(13) H(4) 2.575(8) ? . 1_565 H(13) H(5) 2.556(7) ? . 1_565 H(13) H(7) 2.338 ? . 1_565 H(14) O(8) 3.203 ? . 1_666 H(14) C(3) 3.488 ? . 1_665 H(14) C(20) 3.455 ? . 1_656 H(14) H(3) 2.540 ? . 1_665 H(14) H(5) 2.968 ? . 1_565 H(14) H(23) 2.704 ? . 1_656 H(14) H(24) 3.405 ? . 1_656 H(14) H(30) 2.894 ? . 1_666 H(15) O(4) 3.260(5) ? . 1_655 H(15) C(3) 3.210(6) ? . 1_665 H(15) C(15) 3.538(7) ? . 1_655 H(15) H(3) 2.465(6) ? . 1_665 H(15) H(4) 3.073(6) ? . 1_665 H(15) H(10) 3.504(7) ? . 1_655 H(15) H(18) 2.733(7) ? . 1_655 H(15) H(23) 3.415(5) ? . 1_656 H(15) H(24) 2.949(5) ? . 1_656 H(15) H(28) 3.431(6) ? . 1_656 H(16) O(6) 2.598(5) ? . 1_656 H(16) C(20) 2.961(4) ? . 1_656 H(16) C(21) 3.292(5) ? . 1_656 H(16) C(25) 3.489(6) ? . 1_656 H(16) C(27) 3.321(6) ? . 1_656 H(16) C(32) 3.547(7) ? . 1_656 H(16) H(18) 3.319(7) ? . 1_655 H(16) H(23) 2.937(5) ? . 1_656 H(16) H(24) 2.369(5) ? . 1_656 H(16) H(28) 2.452(6) ? . 1_656 H(16) H(35) 2.836(7) ? . 1_656 H(17) O(8) 3.085(6) ? . 1_556 H(17) C(27) 3.588(6) ? . 1_556 H(17) C(32) 3.311(7) ? . 1_656 H(17) H(28) 3.309(6) ? . 1_556 H(17) H(29) 3.273(6) ? . 1_556 H(17) H(35) 2.432(7) ? . 1_656 H(17) H(36) 3.430(7) ? . 1_656 H(18) O(2) 3.511(5) ? . 1_455 H(18) O(3) 2.848(5) ? . 1_455 H(18) O(8) 3.526(6) ? . 1_556 H(18) C(8) 3.344(6) ? . 1_455 H(18) C(9) 3.478(6) ? . 1_455 H(18) C(14) 3.306(7) ? . 1_455 H(18) H(15) 2.733(7) ? . 1_455 H(18) H(16) 3.319(7) ? . 1_455 H(18) H(28) 3.236(6) ? . 1_556 H(19) O(4) 2.936(6) ? . 1_554 H(19) O(6) 2.948(6) ? . 1_655 H(19) O(7) 3.215(7) ? . 1_655 H(19) C(21) 3.514(7) ? . 1_655 H(19) C(24) 3.224(8) ? . 1_655 H(19) H(25) 2.993 ? . 1_655 H(19) H(27) 3.445(6) ? . 1_655 H(20) O(1) 3.514(5) ? . 1_665 H(20) C(7) 3.359(6) ? . 1_565 H(20) C(30) 3.240(7) ? . 1_665 H(20) H(8) 2.533(6) ? . 1_565 H(20) H(9) 3.348(7) ? . 1_565 H(20) H(25) 2.791 ? . 1_655 H(20) H(27) 2.953(7) ? . 1_655 H(20) H(31) 2.536(7) ? . 1_665 H(20) H(32) 3.094(7) ? . 1_665 H(21) O(1) 2.954(6) ? . 1_565 H(21) C(7) 3.263(5) ? . 1_565 H(21) C(30) 3.453(7) ? . 1_565 H(21) H(8) 3.031(6) ? . 1_565 H(21) H(9) 2.656(5) ? . 1_565 H(21) H(31) 3.079(6) ? . 1_665 H(21) H(32) 2.579(7) ? . 1_565 H(21) H(33) 3.090(7) ? . 1_565 H(21) H(36) 3.089(7) ? . 1_665 H(22) O(4) 2.882(6) ? . 1_554 H(22) C(29) 3.006(6) ? . 1_665 H(22) C(30) 3.210(6) ? . 1_665 H(22) C(32) 3.165(7) ? . 1_665 H(22) H(5) 3.514(7) ? . 1_564 H(22) H(30) 2.521 ? . 1_665 H(22) H(31) 2.646(5) ? . 1_665 H(22) H(32) 3.513(6) ? . 1_665 H(22) H(36) 2.507(7) ? . 1_665 H(23) O(8) 2.898(6) ? . 1_565 H(23) C(13) 3.388(5) ? . 1_454 H(23) C(14) 3.397(5) ? . 1_454 H(23) C(28) 3.340(7) ? . 1_565 H(23) C(29) 3.372(7) ? . 1_565 H(23) C(30) 3.370(7) ? . 1_565 H(23) H(3) 3.477(6) ? . 1_564 H(23) H(14) 2.704 ? . 1_454 H(23) H(15) 3.415(5) ? . 1_454 H(23) H(16) 2.937(5) ? . 1_454 H(23) H(30) 3.003 ? . 1_565 H(23) H(32) 2.595(6) ? . 1_565 H(24) O(4) 2.479(6) ? . 1_554 H(24) C(14) 3.047(5) ? . 1_454 H(24) C(16) 3.550(6) ? . 1_554 H(24) H(14) 3.405 ? . 1_454 H(24) H(15) 2.949(5) ? . 1_454 H(24) H(16) 2.369(5) ? . 1_454 H(25) O(1) 2.862 ? . 1_565 H(25) C(18) 3.355 ? . 1_455 H(25) C(30) 3.191 ? . 1_565 H(25) H(19) 2.993 ? . 1_455 H(25) H(20) 2.791 ? . 1_455 H(25) H(31) 3.319 ? . 1_565 H(25) H(32) 2.306 ? . 1_565 H(26) O(3) 2.658(6) ? . 1_455 H(26) C(3) 3.460(5) ? . 1_565 H(26) C(8) 3.559(6) ? . 1_455 H(26) H(1) 3.311(7) ? . 1_565 H(26) H(4) 2.631(5) ? . 1_565 H(26) H(10) 2.861(7) ? . . H(26) H(12) 3.106(7) ? . 1_455 H(27) O(1) 2.663(5) ? . 1_565 H(27) C(1) 3.091(5) ? . 1_565 H(27) C(2) 3.114(5) ? . 1_565 H(27) C(3) 3.580(5) ? . 1_565 H(27) C(18) 3.568(7) ? . 1_455 H(27) H(1) 2.540(6) ? . 1_565 H(27) H(4) 3.064(6) ? . 1_565 H(27) H(12) 3.202(7) ? . 1_455 H(27) H(19) 3.445(6) ? . 1_455 H(27) H(20) 2.953(7) ? . 1_455 H(28) O(4) 3.108(6) ? . 1_554 H(28) C(14) 3.323(6) ? . 1_454 H(28) C(15) 3.567(6) ? . 1_554 H(28) H(15) 3.431(6) ? . 1_454 H(28) H(16) 2.452(6) ? . 1_454 H(28) H(17) 3.309(6) ? . 1_554 H(28) H(18) 3.236(6) ? . 1_554 H(29) O(4) 3.599(6) ? . 1_554 H(29) O(6) 3.523(5) ? . 1_655 H(29) O(7) 2.833(5) ? . 1_655 H(29) C(24) 3.341(6) ? . 1_655 H(29) C(25) 3.498(7) ? . 1_655 H(29) C(32) 3.273(7) ? . 1_655 H(29) H(17) 3.273(6) ? . 1_554 H(29) H(35) 3.295(7) ? . 1_655 H(29) H(36) 2.688(7) ? . 1_655 H(30) O(4) 3.164 ? . 1_444 H(30) C(4) 3.451 ? . 1_454 H(30) C(19) 3.472 ? . 1_445 H(30) H(5) 2.713 ? . 1_454 H(30) H(6) 3.375 ? . 1_454 H(30) H(14) 2.894 ? . 1_444 H(30) H(22) 2.521 ? . 1_445 H(30) H(23) 3.003 ? . 1_545 H(31) O(1) 3.163(6) ? . . H(31) O(3) 3.519(5) ? . 1_455 H(31) C(7) 3.522(7) ? . 1_455 H(31) C(18) 3.223(6) ? . 1_445 H(31) C(19) 3.121(6) ? . 1_445 H(31) H(8) 3.203(7) ? . 1_455 H(31) H(9) 3.169(7) ? . 1_455 H(31) H(20) 2.536(7) ? . 1_445 H(31) H(21) 3.079(6) ? . 1_445 H(31) H(22) 2.646(5) ? . 1_445 H(31) H(25) 3.319 ? . 1_545 H(32) O(1) 2.667(6) ? . . H(32) C(19) 3.237(7) ? . 1_545 H(32) C(20) 3.054(7) ? . 1_545 H(32) C(21) 3.077(7) ? . 1_545 H(32) H(20) 3.094(7) ? . 1_445 H(32) H(21) 2.579(7) ? . 1_545 H(32) H(22) 3.513(6) ? . 1_445 H(32) H(23) 2.595(6) ? . 1_545 H(32) H(25) 2.306 ? . 1_545 H(33) O(1) 3.157(6) ? . . H(33) O(7) 2.494(5) ? . 1_655 H(33) C(11) 3.492(5) ? . . H(33) H(9) 2.863(7) ? . . H(33) H(10) 3.340(6) ? . . H(33) H(11) 2.755(5) ? . . H(33) H(21) 3.090(7) ? . 1_545 H(33) H(36) 3.471(7) ? . 1_655 H(34) O(1) 3.160(7) ? . . H(34) O(3) 2.535(6) ? . 1_455 H(34) C(8) 3.545(6) ? . 1_455 H(34) C(11) 3.322(6) ? . . H(34) H(10) 2.729(5) ? . . H(34) H(11) 3.006(6) ? . . H(35) O(2) 2.618(5) ? . 1_454 H(35) C(4) 2.993(5) ? . 1_454 H(35) C(5) 3.344(6) ? . 1_454 H(35) C(9) 3.504(7) ? . 1_454 H(35) C(14) 3.554(7) ? . 1_454 H(35) C(15) 3.315(7) ? . 1_454 H(35) H(5) 2.994(5) ? . 1_454 H(35) H(6) 2.370(5) ? . 1_454 H(35) H(16) 2.836(7) ? . 1_454 H(35) H(17) 2.432(7) ? . 1_454 H(35) H(29) 3.295(7) ? . 1_455 H(36) O(8) 3.243(5) ? . 1_455 H(36) C(19) 3.241(7) ? . 1_445 H(36) C(27) 3.510(7) ? . 1_455 H(36) C(28) 3.585(6) ? . 1_455 H(36) H(5) 3.492(6) ? . 1_454 H(36) H(6) 2.970(6) ? . 1_454 H(36) H(17) 3.430(7) ? . 1_454 H(36) H(21) 3.089(7) ? . 1_445 H(36) H(22) 2.507(7) ? . 1_445 H(36) H(29) 2.688(7) ? . 1_455 H(36) H(33) 3.471(7) ? . 1_455 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Attachment 'Compound 12.cif' data_12 _database_code_depnum_ccdc_archive 'CCDC 748550' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 O5' _chemical_formula_sum 'C17 H18 O5' _chemical_formula_weight 302.31 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 7.9585(16) _cell_length_b 17.241(3) _cell_length_c 20.159(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2766.0(10) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5939 _cell_measurement_theta_min 2.0204 _cell_measurement_theta_max 31.1037 _exptl_crystal_description Needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details 'Blessing, R.H. (1995) Acta Cryst A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11370 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3418 _reflns_number_gt 3136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-3 _computing_publication_material ? _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^)+(0.0566P)^2^+1.7419P] 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_number_reflns 3418 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1384 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.001 _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 O3 O 0.45531(15) 0.16947(7) 0.71975(6) 0.0209(3) Uani 1 1 d . . . O1 O 0.68167(15) 0.07056(7) 0.52423(6) 0.0200(3) Uani 1 1 d . . . O4 O 0.93943(15) 0.12461(7) 0.59870(6) 0.0234(3) Uani 1 1 d . . . O2 O 0.39002(16) -0.14099(7) 0.65179(7) 0.0252(3) Uani 1 1 d . . . O5 O 1.03747(18) 0.00360(8) 0.59990(10) 0.0466(5) Uani 1 1 d . . . C1 C 0.4550(2) -0.00631(9) 0.63019(8) 0.0181(3) Uani 1 1 d . . . H1A H 0.3719 0.0101 0.6640 0.022 Uiso 1 1 calc R . . H1B H 0.4054 0.0025 0.5858 0.022 Uiso 1 1 calc R . . C2 C 0.6173(2) 0.04246(9) 0.63755(8) 0.0169(3) Uani 1 1 d . . . C3 C 0.4942(2) -0.09148(9) 0.63888(8) 0.0195(3) Uani 1 1 d . . . C4 C 0.6079(2) 0.13545(9) 0.55298(8) 0.0182(3) Uani 1 1 d . . . C5 C 0.4552(2) 0.25392(9) 0.62124(9) 0.0212(3) Uani 1 1 d . . . H5 H 0.4048 0.2958 0.6446 0.025 Uiso 1 1 calc R . . C6 C 0.7614(2) -0.06875(10) 0.69336(9) 0.0245(4) Uani 1 1 d . . . H6A H 0.8852 -0.0701 0.6888 0.029 Uiso 1 1 calc R . . H6B H 0.7305 -0.0993 0.7331 0.029 Uiso 1 1 calc R . . C7 C 0.5750(2) 0.12578(9) 0.62028(8) 0.0170(3) Uani 1 1 d . . . C8 C 0.4945(2) 0.18484(9) 0.65467(8) 0.0180(3) Uani 1 1 d . . . C9 C 0.9226(2) 0.04790(10) 0.59357(9) 0.0223(4) Uani 1 1 d . . . C10 C 0.7394(2) 0.02294(9) 0.57931(8) 0.0181(3) Uani 1 1 d . . . C11 C 0.4903(2) 0.26097(10) 0.55382(9) 0.0219(4) Uani 1 1 d . . . H11 H 0.4607 0.3076 0.5316 0.026 Uiso 1 1 calc R . . C12 C 0.7018(2) 0.01766(9) 0.70251(8) 0.0206(3) Uani 1 1 d . . . H12A H 0.6214 0.0215 0.7398 0.025 Uiso 1 1 calc R . . H12B H 0.7992 0.0516 0.7122 0.025 Uiso 1 1 calc R . . C13 C 0.5676(2) 0.20170(10) 0.51774(8) 0.0218(3) Uani 1 1 d . . . H13 H 0.5910 0.2066 0.4717 0.026 Uiso 1 1 calc R . . C14 C 0.6791(2) -0.10561(10) 0.63087(9) 0.0216(3) Uani 1 1 d . . . H14 H 0.7037 -0.1624 0.6285 0.026 Uiso 1 1 calc R . . C15 C 1.1077(2) 0.15147(10) 0.61356(9) 0.0237(4) Uani 1 1 d . . . H15A H 1.1481 0.1262 0.6541 0.036 Uiso 1 1 calc R . . H15B H 1.1062 0.2078 0.6201 0.036 Uiso 1 1 calc R . . H15C H 1.1826 0.1387 0.5766 0.036 Uiso 1 1 calc R . . C16 C 0.7335(2) -0.06422(9) 0.56582(9) 0.0217(3) Uani 1 1 d . . . H16A H 0.8456 -0.0829 0.5517 0.026 Uiso 1 1 calc R . . H16B H 0.6521 -0.0755 0.5300 0.026 Uiso 1 1 calc R . . C17 C 0.3696(2) 0.22964(10) 0.75546(9) 0.0242(4) Uani 1 1 d . . . H17A H 0.4432 0.2749 0.7595 0.036 Uiso 1 1 calc R . . H17B H 0.3396 0.2108 0.7998 0.036 Uiso 1 1 calc R . . H17C H 0.2673 0.2443 0.7315 0.036 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 O3 0.0230(6) 0.0193(6) 0.0203(6) -0.0018(4) 0.0037(5) 0.0026(4) O1 0.0218(6) 0.0187(6) 0.0195(6) -0.0005(4) 0.0010(5) 0.0012(4) O4 0.0168(6) 0.0195(6) 0.0338(7) -0.0004(5) -0.0032(5) -0.0027(4) O2 0.0236(6) 0.0202(6) 0.0319(7) 0.0026(5) 0.0011(5) -0.0051(5) O5 0.0186(7) 0.0227(7) 0.0984(14) -0.0035(8) -0.0074(8) 0.0025(5) C1 0.0156(7) 0.0167(7) 0.0219(8) 0.0004(6) -0.0001(6) -0.0005(6) C2 0.0156(7) 0.0150(7) 0.0200(7) -0.0008(6) -0.0009(6) 0.0007(5) C3 0.0223(8) 0.0180(8) 0.0181(7) -0.0008(6) -0.0005(6) -0.0009(6) C4 0.0150(7) 0.0178(7) 0.0219(8) -0.0016(6) -0.0005(6) -0.0010(6) C5 0.0169(8) 0.0164(7) 0.0302(9) -0.0008(6) -0.0009(6) 0.0007(6) C6 0.0238(9) 0.0189(8) 0.0307(9) 0.0001(7) -0.0062(7) 0.0025(6) C7 0.0147(7) 0.0161(7) 0.0201(8) 0.0002(6) -0.0014(6) -0.0007(5) C8 0.0146(7) 0.0180(7) 0.0214(8) -0.0004(6) -0.0008(6) -0.0020(6) C9 0.0190(8) 0.0200(8) 0.0279(9) -0.0009(6) 0.0014(7) -0.0015(6) C10 0.0164(8) 0.0168(8) 0.0213(7) 0.0001(6) -0.0012(6) -0.0005(6) C11 0.0191(8) 0.0174(8) 0.0292(9) 0.0049(7) -0.0038(7) -0.0015(6) C12 0.0227(8) 0.0184(8) 0.0207(8) -0.0002(6) -0.0044(6) 0.0009(6) C13 0.0215(8) 0.0217(8) 0.0222(8) 0.0038(6) -0.0019(6) -0.0029(6) C14 0.0211(8) 0.0160(7) 0.0279(8) -0.0003(6) -0.0016(7) 0.0003(6) C15 0.0167(8) 0.0241(8) 0.0303(9) 0.0005(7) -0.0014(7) -0.0042(6) C16 0.0219(8) 0.0169(8) 0.0263(8) -0.0027(6) 0.0032(7) -0.0001(6) C17 0.0235(9) 0.0235(8) 0.0256(8) -0.0063(7) 0.0033(7) 0.0019(6) _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 O3 C8 1.374(2) . ? O3 C17 1.4354(19) . ? O1 C4 1.3900(19) . ? O1 C10 1.4553(19) . ? O4 C9 1.333(2) . ? O4 C15 1.448(2) . ? O2 C3 1.218(2) . ? O5 C9 1.198(2) . ? C1 C3 1.511(2) . ? C1 C2 1.549(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C7 1.516(2) . ? C2 C12 1.533(2) . ? C2 C10 1.560(2) . ? C3 C14 1.501(2) . ? C4 C13 1.383(2) . ? C4 C7 1.392(2) . ? C5 C11 1.393(2) . ? C5 C8 1.404(2) . ? C5 H5 0.9500 . ? C6 C14 1.555(2) . ? C6 C12 1.574(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.389(2) . ? C9 C10 1.548(2) . ? C10 C16 1.528(2) . ? C11 C13 1.397(2) . ? C11 H11 0.9500 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13 0.9500 . ? C14 C16 1.554(2) . ? C14 H14 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? 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 C8 O3 C17 116.57(13) . . ? C4 O1 C10 105.61(12) . . ? C9 O4 C15 115.22(13) . . ? C3 C1 C2 110.12(13) . . ? C3 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? C3 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.2 . . ? C7 C2 C12 123.92(13) . . ? C7 C2 C1 107.88(13) . . ? C12 C2 C1 107.24(13) . . ? C7 C2 C10 99.77(12) . . ? C12 C2 C10 108.03(13) . . ? C1 C2 C10 109.27(13) . . ? O2 C3 C14 125.22(16) . . ? O2 C3 C1 124.40(15) . . ? C14 C3 C1 110.36(14) . . ? C13 C4 O1 123.27(15) . . ? C13 C4 C7 123.78(15) . . ? O1 C4 C7 112.92(14) . . ? C11 C5 C8 119.87(15) . . ? C11 C5 H5 120.1 . . ? C8 C5 H5 120.1 . . ? C14 C6 C12 110.79(14) . . ? C14 C6 H6A 109.5 . . ? C12 C6 H6A 109.5 . . ? C14 C6 H6B 109.5 . . ? C12 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C4 119.06(15) . . ? C8 C7 C2 133.05(15) . . ? C4 C7 C2 107.20(13) . . ? O3 C8 C7 116.10(14) . . ? O3 C8 C5 124.85(15) . . ? C7 C8 C5 119.03(15) . . ? O5 C9 O4 123.19(16) . . ? O5 C9 C10 124.17(16) . . ? O4 C9 C10 112.64(14) . . ? O1 C10 C16 114.17(13) . . ? O1 C10 C9 106.38(13) . . ? C16 C10 C9 109.60(13) . . ? O1 C10 C2 104.84(12) . . ? C16 C10 C2 109.09(13) . . ? C9 C10 C2 112.75(13) . . ? C5 C11 C13 122.17(15) . . ? C5 C11 H11 118.9 . . ? C13 C11 H11 118.9 . . ? C2 C12 C6 107.22(13) . . ? C2 C12 H12A 110.3 . . ? C6 C12 H12A 110.3 . . ? C2 C12 H12B 110.3 . . ? C6 C12 H12B 110.3 . . ? H12A C12 H12B 108.5 . . ? C4 C13 C11 116.04(15) . . ? C4 C13 H13 122.0 . . ? C11 C13 H13 122.0 . . ? C3 C14 C16 106.81(14) . . ? C3 C14 C6 105.03(14) . . ? C16 C14 C6 112.24(14) . . ? C3 C14 H14 110.8 . . ? C16 C14 H14 110.8 . . ? C6 C14 H14 110.8 . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 C14 108.05(13) . . ? C10 C16 H16A 110.1 . . ? C14 C16 H16A 110.1 . . ? C10 C16 H16B 110.1 . . ? C14 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? O3 C17 H17A 109.5 . . ? O3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.298 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.055 # Attachment 'Compound 15.cif' data_15 _database_code_depnum_ccdc_archive 'CCDC 748551' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O4' _chemical_formula_sum 'C16 H18 O4' _chemical_formula_weight 274.30 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7342(13) _cell_length_b 8.6721(17) _cell_length_c 11.458(2) _cell_angle_alpha 102.25(3) _cell_angle_beta 98.41(3) _cell_angle_gamma 104.21(3) _cell_volume 619.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2498 _cell_measurement_theta_min 1.8600 _cell_measurement_theta_max 30.9188 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9750 _exptl_absorpt_process_details 'Blessing, R.H. (1995) Acta Cryst A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8536 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2987 _reflns_number_gt 2919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0500P)^2^+0.2868P] 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_number_reflns 2987 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _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 O3 O 0.94309(11) 0.33020(9) 0.83046(7) 0.01362(16) Uani 1 1 d . . . O2 O 1.16269(13) 0.46527(11) 0.62179(8) 0.02097(19) Uani 1 1 d . . . O1 O 0.35923(13) 0.15064(10) 0.50115(7) 0.02170(19) Uani 1 1 d . . . O4 O 0.67824(15) 0.77408(11) 0.98475(8) 0.0257(2) Uani 1 1 d . . . C1 C 0.99954(16) 0.41154(12) 0.65099(9) 0.0136(2) Uani 1 1 d . . . C2 C 0.68818(16) 0.57724(12) 0.65842(9) 0.0135(2) Uani 1 1 d . . . H2A H 0.5444 0.5886 0.6489 0.016 Uiso 1 1 calc R . . H2B H 0.7145 0.5373 0.5762 0.016 Uiso 1 1 calc R . . C3 C 1.06851(16) 0.63094(12) 0.86137(9) 0.0142(2) Uani 1 1 d . . . H3A H 1.2001 0.6738 0.8349 0.017 Uiso 1 1 calc R . . H3B H 1.1047 0.6187 0.9452 0.017 Uiso 1 1 calc R . . C4 C 0.62444(16) 0.50722(12) 0.84920(9) 0.0140(2) Uani 1 1 d . . . H4A H 0.4722 0.4927 0.8260 0.017 Uiso 1 1 calc R . . H4B H 0.6471 0.4400 0.9070 0.017 Uiso 1 1 calc R . . C5 C 0.71064(15) 0.45319(12) 0.73531(9) 0.01120(19) Uani 1 1 d . . . C6 C 0.62841(17) 0.11822(13) 0.84096(9) 0.0155(2) Uani 1 1 d . . . H6A H 0.6064 0.2070 0.9034 0.019 Uiso 1 1 calc R . . H6B H 0.7009 0.0530 0.8836 0.019 Uiso 1 1 calc R . . C7 C 0.43066(16) 0.17345(12) 0.60924(10) 0.0145(2) Uani 1 1 d . . . C8 C 0.65784(16) 0.26659(12) 0.66453(9) 0.0125(2) Uani 1 1 d . . . C9 C 0.76288(16) 0.19307(12) 0.76073(9) 0.0142(2) Uani 1 1 d . . . H9 H 0.8173 0.1055 0.7161 0.017 Uiso 1 1 calc R . . C10 C 0.80637(16) 0.27670(12) 0.57368(9) 0.0148(2) Uani 1 1 d . . . H10A H 0.8388 0.1710 0.5469 0.018 Uiso 1 1 calc R . . H10B H 0.7460 0.3080 0.5012 0.018 Uiso 1 1 calc R . . C11 C 0.93279(16) 0.75079(12) 0.85915(9) 0.0146(2) Uani 1 1 d . . . H11 H 1.0144 0.8651 0.9072 0.018 Uiso 1 1 calc R . . C12 C 0.30307(17) 0.10569(13) 0.69464(10) 0.0174(2) Uani 1 1 d . . . H12A H 0.1645 0.0332 0.6472 0.021 Uiso 1 1 calc R . . H12B H 0.2802 0.1975 0.7539 0.021 Uiso 1 1 calc R . . C13 C 0.94323(15) 0.46641(12) 0.77535(9) 0.01146(19) Uani 1 1 d . . . C14 C 0.74059(17) 0.68863(13) 0.90865(10) 0.0156(2) Uani 1 1 d . . . C15 C 0.41695(17) 0.00737(13) 0.76392(10) 0.0173(2) Uani 1 1 d . . . H15A H 0.3295 -0.0391 0.8175 0.021 Uiso 1 1 calc R . . H15B H 0.4385 -0.0852 0.7047 0.021 Uiso 1 1 calc R . . C16 C 0.84961(17) 0.74621(13) 0.72500(10) 0.0158(2) Uani 1 1 d . . . H16A H 0.9679 0.7648 0.6826 0.019 Uiso 1 1 calc R . . H16B H 0.7824 0.8354 0.7227 0.019 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 O3 0.0137(3) 0.0118(3) 0.0145(3) 0.0048(3) 0.0002(3) 0.0023(3) O2 0.0159(4) 0.0268(4) 0.0202(4) 0.0059(3) 0.0078(3) 0.0038(3) O1 0.0207(4) 0.0226(4) 0.0171(4) 0.0057(3) -0.0028(3) 0.0012(3) O4 0.0311(5) 0.0208(4) 0.0249(4) -0.0010(3) 0.0131(4) 0.0087(3) C1 0.0138(5) 0.0146(4) 0.0138(4) 0.0042(4) 0.0036(4) 0.0055(4) C2 0.0139(5) 0.0129(4) 0.0134(4) 0.0047(4) 0.0012(4) 0.0033(4) C3 0.0136(5) 0.0128(4) 0.0141(5) 0.0020(4) 0.0012(4) 0.0023(4) C4 0.0149(5) 0.0138(4) 0.0140(4) 0.0032(4) 0.0056(4) 0.0043(4) C5 0.0114(4) 0.0106(4) 0.0110(4) 0.0022(3) 0.0026(3) 0.0024(3) C6 0.0173(5) 0.0140(5) 0.0145(5) 0.0052(4) 0.0033(4) 0.0019(4) C7 0.0151(5) 0.0105(4) 0.0164(5) 0.0023(3) 0.0015(4) 0.0030(3) C8 0.0134(5) 0.0121(4) 0.0116(4) 0.0030(3) 0.0028(4) 0.0029(3) C9 0.0143(5) 0.0121(4) 0.0146(5) 0.0035(4) 0.0016(4) 0.0019(4) C10 0.0161(5) 0.0143(5) 0.0125(4) 0.0008(3) 0.0043(4) 0.0032(4) C11 0.0160(5) 0.0114(4) 0.0147(5) 0.0016(3) 0.0026(4) 0.0027(4) C12 0.0142(5) 0.0170(5) 0.0183(5) 0.0031(4) 0.0036(4) 0.0010(4) C13 0.0118(4) 0.0112(4) 0.0117(4) 0.0037(3) 0.0027(3) 0.0033(3) C14 0.0185(5) 0.0149(5) 0.0140(5) 0.0029(4) 0.0037(4) 0.0063(4) C15 0.0185(5) 0.0136(5) 0.0177(5) 0.0041(4) 0.0045(4) 0.0001(4) C16 0.0177(5) 0.0123(4) 0.0167(5) 0.0049(4) 0.0023(4) 0.0026(4) _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 O3 C13 1.4527(12) . ? O3 C9 1.4595(14) . ? O2 C1 1.2077(14) . ? O1 C7 1.2163(14) . ? O4 C14 1.2130(14) . ? C1 C10 1.5234(16) . ? C1 C13 1.5361(14) . ? C2 C5 1.5489(14) . ? C2 C16 1.5531(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C13 1.5126(15) . ? C3 C11 1.5450(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C14 1.5284(15) . ? C4 C5 1.5346(14) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C13 1.5350(14) . ? C5 C8 1.5745(14) . ? C6 C9 1.5147(15) . ? C6 C15 1.5269(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.5111(15) . ? C7 C8 1.5122(15) . ? C8 C10 1.5466(14) . ? C8 C9 1.5536(14) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C14 1.5131(15) . ? C11 C16 1.5456(15) . ? C11 H11 1.0000 . ? C12 C15 1.5412(16) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? 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 C13 O3 C9 107.02(8) . . ? O2 C1 C10 127.91(10) . . ? O2 C1 C13 126.80(10) . . ? C10 C1 C13 105.29(9) . . ? C5 C2 C16 108.52(8) . . ? C5 C2 H2A 110.0 . . ? C16 C2 H2A 110.0 . . ? C5 C2 H2B 110.0 . . ? C16 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? C13 C3 C11 107.86(8) . . ? C13 C3 H3A 110.1 . . ? C11 C3 H3A 110.1 . . ? C13 C3 H3B 110.1 . . ? C11 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C14 C4 C5 107.66(9) . . ? C14 C4 H4A 110.2 . . ? C5 C4 H4A 110.2 . . ? C14 C4 H4B 110.2 . . ? C5 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? C4 C5 C13 108.77(8) . . ? C4 C5 C2 105.70(8) . . ? C13 C5 C2 109.62(8) . . ? C4 C5 C8 121.77(8) . . ? C13 C5 C8 92.26(8) . . ? C2 C5 C8 117.33(8) . . ? C9 C6 C15 110.29(9) . . ? C9 C6 H6A 109.6 . . ? C15 C6 H6A 109.6 . . ? C9 C6 H6B 109.6 . . ? C15 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O1 C7 C12 122.72(10) . . ? O1 C7 C8 121.10(10) . . ? C12 C7 C8 116.13(9) . . ? C7 C8 C10 115.78(9) . . ? C7 C8 C9 113.83(9) . . ? C10 C8 C9 103.71(8) . . ? C7 C8 C5 117.94(9) . . ? C10 C8 C5 101.22(8) . . ? C9 C8 C5 102.31(8) . . ? O3 C9 C6 112.84(9) . . ? O3 C9 C8 103.15(8) . . ? C6 C9 C8 117.45(9) . . ? O3 C9 H9 107.6 . . ? C6 C9 H9 107.6 . . ? C8 C9 H9 107.6 . . ? C1 C10 C8 101.68(8) . . ? C1 C10 H10A 111.4 . . ? C8 C10 H10A 111.4 . . ? C1 C10 H10B 111.4 . . ? C8 C10 H10B 111.4 . . ? H10A C10 H10B 109.3 . . ? C14 C11 C3 108.99(9) . . ? C14 C11 C16 105.57(9) . . ? C3 C11 C16 108.93(9) . . ? C14 C11 H11 111.1 . . ? C3 C11 H11 111.1 . . ? C16 C11 H11 111.1 . . ? C7 C12 C15 110.50(9) . . ? C7 C12 H12A 109.6 . . ? C15 C12 H12A 109.6 . . ? C7 C12 H12B 109.6 . . ? C15 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O3 C13 C3 112.50(8) . . ? O3 C13 C5 104.59(8) . . ? C3 C13 C5 113.33(9) . . ? O3 C13 C1 104.45(8) . . ? C3 C13 C1 119.54(9) . . ? C5 C13 C1 100.76(8) . . ? O4 C14 C11 124.10(10) . . ? O4 C14 C4 122.46(10) . . ? C11 C14 C4 113.39(9) . . ? C6 C15 C12 110.49(9) . . ? C6 C15 H15A 109.6 . . ? C12 C15 H15A 109.6 . . ? C6 C15 H15B 109.6 . . ? C12 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C11 C16 C2 110.39(9) . . ? C11 C16 H16A 109.6 . . ? C2 C16 H16A 109.6 . . ? C11 C16 H16B 109.6 . . ? C2 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.365 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.049