data_cd211406 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 O3' _chemical_formula_weight 348.51 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 P2(1)2(1)2(1) 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' _cell_length_a 8.1087(6) _cell_length_b 11.9482(9) _cell_length_c 20.2320(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1960.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4410 _cell_measurement_theta_min 5.276 _cell_measurement_theta_max 54.036 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.317 _exptl_crystal_size_mid 0.269 _exptl_crystal_size_min 0.213 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.56483 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10653 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3829 _reflns_number_gt 3495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0588P)^2^+0.1869P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(11) _chemical_absolute_configuration ad _refine_ls_number_reflns 3829 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 O1 O 0.99837(16) 0.30030(11) 0.16891(6) 0.0537(3) Uani 1 1 d . . . O2 O 0.69385(18) -0.18334(11) -0.00038(7) 0.0635(4) Uani 1 1 d . . . H2 H 0.6256 -0.2155 -0.0235 0.095 Uiso 1 1 calc R . . O3 O 0.38947(17) -0.15884(11) -0.06765(7) 0.0599(4) Uani 1 1 d . . . H3 H 0.3292 -0.2035 -0.0485 0.090 Uiso 1 1 calc R . . C1 C 0.5247(3) 0.27697(18) 0.29297(10) 0.0639(6) Uani 1 1 d . . . H1A H 0.5167 0.3502 0.3135 0.077 Uiso 1 1 calc R . . H1B H 0.4147 0.2524 0.2809 0.077 Uiso 1 1 calc R . . C2 C 0.6042(3) 0.1937(2) 0.34028(9) 0.0710(6) Uani 1 1 d . . . H2A H 0.5799 0.2130 0.3858 0.085 Uiso 1 1 calc R . . H2B H 0.5649 0.1184 0.3318 0.085 Uiso 1 1 calc R . . C3 C 0.7852(3) 0.20256(17) 0.32677(8) 0.0576(5) Uani 1 1 d . . . H3A H 0.8575 0.1403 0.3392 0.069 Uiso 1 1 calc R . . C4 C 0.8552(3) 0.31795(17) 0.32298(9) 0.0588(5) Uani 1 1 d . . . H4A H 0.9717 0.3272 0.3323 0.071 Uiso 1 1 calc R . . H4B H 0.7859 0.3796 0.3373 0.071 Uiso 1 1 calc R . . C5 C 0.8077(2) 0.25749(13) 0.26001(8) 0.0440(4) Uani 1 1 d . . . C6 C 0.9422(2) 0.21798(14) 0.21470(8) 0.0440(4) Uani 1 1 d . . . H6 H 1.0358 0.1925 0.2414 0.053 Uiso 1 1 calc R . . C7 C 0.8826(2) 0.12188(14) 0.17226(8) 0.0424(4) Uani 1 1 d . . . H7A H 0.8618 0.0573 0.2001 0.051 Uiso 1 1 calc R . . H7B H 0.9682 0.1019 0.1409 0.051 Uiso 1 1 calc R . . C8 C 0.72563(19) 0.15180(12) 0.13480(7) 0.0335(3) Uani 1 1 d . . . H8 H 0.7489 0.2147 0.1051 0.040 Uiso 1 1 calc R . . C9 C 0.5876(2) 0.18631(13) 0.18314(8) 0.0390(4) Uani 1 1 d . . . H9 H 0.5668 0.1206 0.2109 0.047 Uiso 1 1 calc R . . C10 C 0.6361(2) 0.28218(14) 0.23140(8) 0.0432(4) Uani 1 1 d . . . C11 C 0.4262(2) 0.20865(16) 0.14593(10) 0.0511(5) Uani 1 1 d . . . H11A H 0.3398 0.2237 0.1778 0.061 Uiso 1 1 calc R . . H11B H 0.4398 0.2752 0.1190 0.061 Uiso 1 1 calc R . . C12 C 0.3719(2) 0.11215(15) 0.10171(9) 0.0462(4) Uani 1 1 d . . . H12A H 0.2740 0.1341 0.0774 0.055 Uiso 1 1 calc R . . H12B H 0.3437 0.0482 0.1290 0.055 Uiso 1 1 calc R . . C13 C 0.50733(19) 0.07865(12) 0.05290(7) 0.0347(3) Uani 1 1 d . . . C14 C 0.66284(18) 0.05356(12) 0.09403(7) 0.0335(3) Uani 1 1 d . . . H14 H 0.6303 -0.0039 0.1260 0.040 Uiso 1 1 calc R . . C15 C 0.7790(2) -0.00435(15) 0.04570(8) 0.0452(4) Uani 1 1 d . . . H15A H 0.8508 -0.0565 0.0686 0.054 Uiso 1 1 calc R . . H15B H 0.8464 0.0500 0.0224 0.054 Uiso 1 1 calc R . . C16 C 0.6647(2) -0.06635(14) -0.00240(8) 0.0426(4) Uani 1 1 d . . . H16 H 0.6850 -0.0391 -0.0474 0.051 Uiso 1 1 calc R . . C17 C 0.4870(2) -0.03608(12) 0.01793(7) 0.0364(3) Uani 1 1 d . . . H17 H 0.4535 -0.0901 0.0518 0.044 Uiso 1 1 calc R . . C18 C 0.5350(2) 0.17175(14) 0.00187(8) 0.0481(4) Uani 1 1 d . . . H18A H 0.4364 0.1821 -0.0236 0.072 Uiso 1 1 calc R . . H18B H 0.6241 0.1512 -0.0270 0.072 Uiso 1 1 calc R . . H18C H 0.5620 0.2402 0.0243 0.072 Uiso 1 1 calc R . . C19 C 0.6280(3) 0.39681(14) 0.19836(11) 0.0564(5) Uani 1 1 d . . . H19A H 0.6702 0.4526 0.2280 0.085 Uiso 1 1 calc R . . H19B H 0.5155 0.4140 0.1875 0.085 Uiso 1 1 calc R . . H19C H 0.6931 0.3960 0.1587 0.085 Uiso 1 1 calc R . . C20 C 0.3675(2) -0.04921(15) -0.03974(8) 0.0456(4) Uani 1 1 d . . . H20 H 0.3977 0.0058 -0.0736 0.055 Uiso 1 1 calc R . . C21 C 0.1888(2) -0.03017(17) -0.02189(11) 0.0583(5) Uani 1 1 d . . . H21A H 0.1201 -0.0511 -0.0585 0.087 Uiso 1 1 calc R . . H21B H 0.1720 0.0475 -0.0118 0.087 Uiso 1 1 calc R . . H21C H 0.1609 -0.0748 0.0159 0.087 Uiso 1 1 calc R . . C22 C 1.0754(3) 0.39472(18) 0.19770(12) 0.0647(5) Uani 1 1 d . . . H22A H 0.9929 0.4438 0.2155 0.097 Uiso 1 1 calc R . . H22B H 1.1379 0.4337 0.1646 0.097 Uiso 1 1 calc R . . H22C H 1.1478 0.3707 0.2325 0.097 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 O1 0.0547(7) 0.0564(7) 0.0498(6) -0.0042(6) -0.0028(6) -0.0145(6) O2 0.0682(9) 0.0449(7) 0.0773(9) -0.0187(6) -0.0158(7) 0.0163(6) O3 0.0569(8) 0.0630(8) 0.0598(8) -0.0246(7) 0.0081(7) -0.0136(6) C1 0.0681(13) 0.0682(12) 0.0555(11) -0.0250(10) 0.0142(11) -0.0014(10) C2 0.1032(18) 0.0715(14) 0.0384(10) -0.0087(9) 0.0161(11) -0.0150(13) C3 0.0865(14) 0.0519(11) 0.0343(8) -0.0009(8) -0.0029(9) 0.0025(10) C4 0.0735(13) 0.0561(11) 0.0469(10) -0.0135(9) -0.0072(9) 0.0019(10) C5 0.0586(11) 0.0365(8) 0.0369(8) -0.0034(6) -0.0048(8) 0.0016(7) C6 0.0467(9) 0.0434(9) 0.0420(9) -0.0029(7) -0.0105(7) 0.0059(7) C7 0.0427(9) 0.0402(8) 0.0444(8) -0.0048(7) -0.0020(7) 0.0068(7) C8 0.0378(8) 0.0296(7) 0.0331(7) 0.0018(6) 0.0017(6) 0.0017(6) C9 0.0437(9) 0.0347(8) 0.0385(8) -0.0028(7) 0.0061(7) 0.0036(7) C10 0.0500(9) 0.0364(8) 0.0433(8) -0.0079(7) 0.0015(8) 0.0066(7) C11 0.0428(10) 0.0527(10) 0.0579(11) -0.0179(9) 0.0024(8) 0.0107(8) C12 0.0351(9) 0.0498(9) 0.0536(9) -0.0089(8) 0.0015(8) 0.0033(7) C13 0.0336(8) 0.0337(7) 0.0369(7) 0.0001(6) -0.0005(6) -0.0006(6) C14 0.0361(8) 0.0321(7) 0.0322(7) 0.0012(6) 0.0039(6) 0.0018(6) C15 0.0376(9) 0.0511(9) 0.0468(9) -0.0109(7) 0.0012(7) 0.0059(7) C16 0.0463(10) 0.0403(8) 0.0411(8) -0.0059(7) 0.0015(7) 0.0043(7) C17 0.0416(9) 0.0336(7) 0.0340(7) 0.0031(6) 0.0044(7) -0.0027(6) C18 0.0572(11) 0.0400(9) 0.0472(9) 0.0072(7) -0.0106(8) -0.0043(8) C19 0.0640(12) 0.0374(9) 0.0679(12) -0.0070(8) -0.0133(10) 0.0088(8) C20 0.0474(10) 0.0461(9) 0.0432(9) -0.0034(7) 0.0008(8) -0.0090(8) C21 0.0458(11) 0.0598(11) 0.0692(12) -0.0141(10) -0.0077(9) -0.0049(9) C22 0.0603(12) 0.0595(12) 0.0742(13) -0.0063(10) -0.0080(11) -0.0153(9) _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 O1 C22 1.415(2) . ? O1 C6 1.426(2) . ? O2 C16 1.418(2) . ? O2 H2 0.8200 . ? O3 C20 1.438(2) . ? O3 H3 0.8200 . ? C1 C2 1.524(3) . ? C1 C10 1.540(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.496(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.493(3) . ? C3 C5 1.513(2) . ? C3 H3A 0.9800 . ? C4 C5 1.514(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.501(2) . ? C5 C10 1.536(3) . ? C6 C7 1.513(2) . ? C6 H6 0.9800 . ? C7 C8 1.524(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C14 1.522(2) . ? C8 C9 1.543(2) . ? C8 H8 0.9800 . ? C9 C11 1.533(2) . ? C9 C10 1.556(2) . ? C9 H9 0.9800 . ? C10 C19 1.526(2) . ? C11 C12 1.524(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.530(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.534(2) . ? C13 C14 1.540(2) . ? C13 C17 1.551(2) . ? C14 C15 1.524(2) . ? C14 H14 0.9800 . ? C15 C16 1.535(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.541(2) . ? C16 H16 0.9800 . ? C17 C20 1.525(2) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.510(3) . ? C20 H20 0.9800 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C22 O1 C6 115.06(14) . . ? C16 O2 H2 109.5 . . ? C20 O3 H3 109.5 . . ? C2 C1 C10 106.64(17) . . ? C2 C1 H1A 110.4 . . ? C10 C1 H1A 110.4 . . ? C2 C1 H1B 110.4 . . ? C10 C1 H1B 110.4 . . ? H1A C1 H1B 108.6 . . ? C3 C2 C1 104.70(17) . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2B 110.8 . . ? C1 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C2 116.6(2) . . ? C4 C3 C5 60.50(11) . . ? C2 C3 C5 108.21(17) . . ? C4 C3 H3A 119.1 . . ? C2 C3 H3A 119.1 . . ? C5 C3 H3A 119.1 . . ? C3 C4 C5 60.40(12) . . ? C3 C4 H4A 117.7 . . ? C5 C4 H4A 117.7 . . ? C3 C4 H4B 117.7 . . ? C5 C4 H4B 117.7 . . ? H4A C4 H4B 114.9 . . ? C6 C5 C3 119.79(15) . . ? C6 C5 C4 118.65(16) . . ? C3 C5 C4 59.11(12) . . ? C6 C5 C10 119.24(13) . . ? C3 C5 C10 108.07(16) . . ? C4 C5 C10 117.11(16) . . ? O1 C6 C5 114.33(14) . . ? O1 C6 C7 104.88(13) . . ? C5 C6 C7 110.71(14) . . ? O1 C6 H6 108.9 . . ? C5 C6 H6 108.9 . . ? C7 C6 H6 108.9 . . ? C6 C7 C8 111.77(13) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C14 C8 C7 111.59(12) . . ? C14 C8 C9 107.88(12) . . ? C7 C8 C9 110.70(12) . . ? C14 C8 H8 108.9 . . ? C7 C8 H8 108.9 . . ? C9 C8 H8 108.9 . . ? C11 C9 C8 110.77(13) . . ? C11 C9 C10 113.33(13) . . ? C8 C9 C10 114.28(13) . . ? C11 C9 H9 105.9 . . ? C8 C9 H9 105.9 . . ? C10 C9 H9 105.9 . . ? C19 C10 C5 112.14(15) . . ? C19 C10 C1 111.43(15) . . ? C5 C10 C1 102.65(14) . . ? C19 C10 C9 112.02(14) . . ? C5 C10 C9 108.93(13) . . ? C1 C10 C9 109.24(15) . . ? C12 C11 C9 113.78(14) . . ? C12 C11 H11A 108.8 . . ? C9 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C9 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 111.67(14) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C18 110.47(13) . . ? C12 C13 C14 106.85(12) . . ? C18 C13 C14 112.63(13) . . ? C12 C13 C17 116.71(13) . . ? C18 C13 C17 110.44(12) . . ? C14 C13 C17 99.28(11) . . ? C8 C14 C15 119.41(13) . . ? C8 C14 C13 114.61(12) . . ? C15 C14 C13 104.35(12) . . ? C8 C14 H14 105.8 . . ? C15 C14 H14 105.8 . . ? C13 C14 H14 105.8 . . ? C14 C15 C16 104.62(13) . . ? C14 C15 H15A 110.8 . . ? C16 C15 H15A 110.8 . . ? C14 C15 H15B 110.8 . . ? C16 C15 H15B 110.8 . . ? H15A C15 H15B 108.9 . . ? O2 C16 C15 110.89(14) . . ? O2 C16 C17 112.31(14) . . ? C15 C16 C17 106.39(12) . . ? O2 C16 H16 109.1 . . ? C15 C16 H16 109.1 . . ? C17 C16 H16 109.1 . . ? C20 C17 C16 111.46(13) . . ? C20 C17 C13 120.48(13) . . ? C16 C17 C13 103.30(12) . . ? C20 C17 H17 107.0 . . ? C16 C17 H17 107.0 . . ? C13 C17 H17 107.0 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 C20 C21 110.51(14) . . ? O3 C20 C17 108.38(14) . . ? C21 C20 C17 114.29(15) . . ? O3 C20 H20 107.8 . . ? C21 C20 H20 107.8 . . ? C17 C20 H20 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O1 C22 H22A 109.5 . . ? O1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 30.5(2) . . . . ? C1 C2 C3 C4 47.2(2) . . . . ? C1 C2 C3 C5 -18.3(2) . . . . ? C2 C3 C4 C5 -96.78(19) . . . . ? C4 C3 C5 C6 107.53(19) . . . . ? C2 C3 C5 C6 -141.65(18) . . . . ? C2 C3 C5 C4 110.8(2) . . . . ? C4 C3 C5 C10 -111.31(17) . . . . ? C2 C3 C5 C10 -0.49(19) . . . . ? C3 C4 C5 C6 -109.44(19) . . . . ? C3 C4 C5 C10 95.73(19) . . . . ? C22 O1 C6 C5 64.5(2) . . . . ? C22 O1 C6 C7 -174.11(15) . . . . ? C3 C5 C6 O1 -154.43(15) . . . . ? C4 C5 C6 O1 -85.62(18) . . . . ? C10 C5 C6 O1 68.67(19) . . . . ? C3 C5 C6 C7 87.40(19) . . . . ? C4 C5 C6 C7 156.21(15) . . . . ? C10 C5 C6 C7 -49.5(2) . . . . ? O1 C6 C7 C8 -69.57(17) . . . . ? C5 C6 C7 C8 54.21(18) . . . . ? C6 C7 C8 C14 -178.02(13) . . . . ? C6 C7 C8 C9 -57.85(17) . . . . ? C14 C8 C9 C11 -53.76(16) . . . . ? C7 C8 C9 C11 -176.11(13) . . . . ? C14 C8 C9 C10 176.78(12) . . . . ? C7 C8 C9 C10 54.42(17) . . . . ? C6 C5 C10 C19 -80.18(19) . . . . ? C3 C5 C10 C19 138.42(15) . . . . ? C4 C5 C10 C19 74.50(19) . . . . ? C6 C5 C10 C1 160.12(15) . . . . ? C3 C5 C10 C1 18.71(18) . . . . ? C4 C5 C10 C1 -45.2(2) . . . . ? C6 C5 C10 C9 44.4(2) . . . . ? C3 C5 C10 C9 -97.01(15) . . . . ? C4 C5 C10 C9 -160.92(15) . . . . ? C2 C1 C10 C19 -150.39(17) . . . . ? C2 C1 C10 C5 -30.18(19) . . . . ? C2 C1 C10 C9 85.31(18) . . . . ? C11 C9 C10 C19 -49.1(2) . . . . ? C8 C9 C10 C19 79.05(18) . . . . ? C11 C9 C10 C5 -173.78(14) . . . . ? C8 C9 C10 C5 -45.60(17) . . . . ? C11 C9 C10 C1 74.82(19) . . . . ? C8 C9 C10 C1 -157.00(14) . . . . ? C8 C9 C11 C12 53.6(2) . . . . ? C10 C9 C11 C12 -176.41(15) . . . . ? C9 C11 C12 C13 -54.8(2) . . . . ? C11 C12 C13 C18 -68.09(18) . . . . ? C11 C12 C13 C14 54.74(18) . . . . ? C11 C12 C13 C17 164.67(14) . . . . ? C7 C8 C14 C15 -53.28(18) . . . . ? C9 C8 C14 C15 -175.09(13) . . . . ? C7 C8 C14 C13 -178.10(12) . . . . ? C9 C8 C14 C13 60.09(15) . . . . ? C12 C13 C14 C8 -60.23(16) . . . . ? C18 C13 C14 C8 61.25(16) . . . . ? C17 C13 C14 C8 178.08(12) . . . . ? C12 C13 C14 C15 167.35(13) . . . . ? C18 C13 C14 C15 -71.17(15) . . . . ? C17 C13 C14 C15 45.66(14) . . . . ? C8 C14 C15 C16 -160.34(13) . . . . ? C13 C14 C15 C16 -30.73(16) . . . . ? C14 C15 C16 O2 -119.27(15) . . . . ? C14 C15 C16 C17 3.12(17) . . . . ? O2 C16 C17 C20 -82.51(17) . . . . ? C15 C16 C17 C20 155.99(13) . . . . ? O2 C16 C17 C13 146.72(13) . . . . ? C15 C16 C17 C13 25.22(16) . . . . ? C12 C13 C17 C20 77.73(18) . . . . ? C18 C13 C17 C20 -49.52(19) . . . . ? C14 C13 C17 C20 -168.01(13) . . . . ? C12 C13 C17 C16 -157.14(14) . . . . ? C18 C13 C17 C16 75.61(15) . . . . ? C14 C13 C17 C16 -42.88(13) . . . . ? C16 C17 C20 O3 51.47(17) . . . . ? C13 C17 C20 O3 172.68(13) . . . . ? C16 C17 C20 C21 175.18(15) . . . . ? C13 C17 C20 C21 -63.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.82 2.22 2.834(2) 132.0 . O3 H3 O2 0.82 2.00 2.8225(18) 176.6 4_445 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.144 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.035