data_dha _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration ad _chemical_formula_moiety 'C18 H32 O4' _chemical_formula_sum 'C18 H32 O4' _chemical_formula_weight 312.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.7567(2) _cell_length_b 11.1781(2) _cell_length_c 10.3340(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.471(8) _cell_angle_gamma 90.00 _cell_volume 934.72(7) _cell_formula_units_Z 2 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 17310 _cell_measurement_theta_min 4.00 _cell_measurement_theta_max 68.30 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9193 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; 3842 images x 1 sec / 8 sec @ 42.00mm; 1.0 deg omega scans; 40kV/30mA ; _diffrn_ambient_temperature 85(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'micro-focus rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn944+ CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 29.257 _diffrn_reflns_number 24668 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.63 _diffrn_reflns_theta_max 68.23 _reflns_number_total 3403 _reflns_number_gt 3309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r12' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r12' _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 ; Standard refinement of the Shelx Flack parameter gave the correct value for the assigned absolute structure although with a somewhat large standard uncertainty. Statistical analysis of the available Bijvoet pairs is unequivocal about the correct assignment. The relavent output from a PLATON run is attached. Space Group P21 Wavelength 1.54178 Flack x .... 0.01(14) Parsons z .. -0.01(7) Bijvoet Pairs 1590 Coverage ... 98 DiffCalcMax. 16.87 Outlier Crit 33.74 Scatter Plot Sigma Crit.. 0.25 Select Pairs 227 Number Plus 156 Number Minus 71 Aver. Ratio 1.052 Slope ...... 1.030 Student-T Prob. Plot Sample Size. 1580 Corr. Coeff. 0.999 Intercept .. 0.107 Slope ...... 0.734 Bayesian Statistics Student_T Nu 24.60 Select Pairs 1590 P2(true).... 1.000 P3(true).... 1.000 P3(rac-twin) 0.4E-09 P3(false) .. 0.5E-38 G .......... 0.9649 G (su) ..... 0.1467 Hooft y .... 0.02(7) 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^)+(0.0383P)^2^+0.1468P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0063(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(14) _refine_ls_number_reflns 3403 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.057 _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 0.59962(12) 0.37701(8) 0.38818(10) 0.0206(2) Uani 1 1 d . . . O2 O 0.50716(14) 0.29465(10) 0.17371(11) 0.0299(2) Uani 1 1 d . . . O3 O 0.07583(12) 0.50752(9) 0.10734(10) 0.0246(2) Uani 1 1 d . . . O4 O 0.65918(13) 0.66055(9) 0.06929(11) 0.0260(2) Uani 1 1 d . . . H4 H 0.609(3) 0.702(2) -0.009(3) 0.048(6) Uiso 1 1 d . . . C1 C 0.48251(18) 0.35138(12) 0.26379(14) 0.0199(3) Uani 1 1 d . . . C2 C 0.31633(18) 0.39847(12) 0.25060(14) 0.0209(3) Uani 1 1 d . . . H2 H 0.3328 0.4586 0.3264 0.025 Uiso 1 1 calc R . . C3 C 0.22816(17) 0.45978(12) 0.10794(14) 0.0203(3) Uani 1 1 d . . . H3 H 0.2016 0.3975 0.0330 0.024 Uiso 1 1 calc R . . C4 C 0.32835(17) 0.55953(12) 0.07457(14) 0.0203(3) Uani 1 1 d . . . H4A H 0.4370 0.5250 0.0829 0.024 Uiso 1 1 calc R . . C5 C 0.36301(18) 0.66412(13) 0.17822(15) 0.0219(3) Uani 1 1 d . . . H5A H 0.4141 0.6313 0.2742 0.026 Uiso 1 1 calc R . . H5B H 0.2557 0.6997 0.1687 0.026 Uiso 1 1 calc R . . C6 C 0.47488(18) 0.76529(12) 0.16356(15) 0.0230(3) Uani 1 1 d . . . H6 H 0.4227 0.7978 0.0663 0.028 Uiso 1 1 calc R . . C7 C 0.65197(18) 0.72439(12) 0.18557(15) 0.0232(3) Uani 1 1 d . . . H7 H 0.7212 0.7979 0.1980 0.028 Uiso 1 1 calc R . . C8 C 0.72955(17) 0.64899(12) 0.31449(14) 0.0226(3) Uani 1 1 d . . . H8 H 0.7284 0.6798 0.3998 0.027 Uiso 1 1 calc R . . C9 C 0.79934(18) 0.54321(13) 0.31925(14) 0.0218(3) Uani 1 1 d . . . H9 H 0.8062 0.5152 0.2349 0.026 Uiso 1 1 calc R . . C10 C 0.86894(18) 0.46291(13) 0.44532(14) 0.0220(3) Uani 1 1 d . . . H10 H 0.9847 0.4429 0.4568 0.026 Uiso 1 1 calc R . . C11 C 0.77104(18) 0.34531(13) 0.41362(14) 0.0209(3) Uani 1 1 d . . . H11 H 0.7754 0.3095 0.3264 0.025 Uiso 1 1 calc R . . C12 C 0.2138(2) 0.29407(15) 0.27114(17) 0.0310(3) Uani 1 1 d . . . H12A H 0.2719 0.2581 0.3635 0.046 Uiso 1 1 calc R . . H12B H 0.1982 0.2338 0.1983 0.046 Uiso 1 1 calc R . . H12C H 0.1058 0.3238 0.2647 0.046 Uiso 1 1 calc R . . C13 C -0.06855(19) 0.46200(15) 0.00083(16) 0.0303(3) Uani 1 1 d . . . H13A H -0.0775 0.3761 0.0153 0.045 Uiso 1 1 calc R . . H13B H -0.0623 0.4753 -0.0908 0.045 Uiso 1 1 calc R . . H13C H -0.1658 0.5031 0.0042 0.045 Uiso 1 1 calc R . . C14 C 0.23797(19) 0.60060(14) -0.07695(15) 0.0261(3) Uani 1 1 d . . . H14A H 0.1332 0.6385 -0.0868 0.039 Uiso 1 1 calc R . . H14B H 0.2160 0.5313 -0.1396 0.039 Uiso 1 1 calc R . . H14C H 0.3069 0.6582 -0.1015 0.039 Uiso 1 1 calc R . . C15 C 0.4811(2) 0.86661(13) 0.26507(17) 0.0289(3) Uani 1 1 d . . . H15A H 0.5507 0.9316 0.2546 0.043 Uiso 1 1 calc R . . H15B H 0.5276 0.8364 0.3614 0.043 Uiso 1 1 calc R . . H15C H 0.3691 0.8967 0.2443 0.043 Uiso 1 1 calc R . . C16 C 0.87799(19) 0.52005(13) 0.58222(14) 0.0263(3) Uani 1 1 d . . . H16A H 0.7659 0.5336 0.5786 0.039 Uiso 1 1 calc R . . H16B H 0.9366 0.5966 0.5954 0.039 Uiso 1 1 calc R . . H16C H 0.9373 0.4666 0.6605 0.039 Uiso 1 1 calc R . . C17 C 0.82684(19) 0.25253(13) 0.52913(16) 0.0259(3) Uani 1 1 d . . . H17A H 0.8044 0.2828 0.6102 0.031 Uiso 1 1 calc R . . H17B H 0.9477 0.2412 0.5600 0.031 Uiso 1 1 calc R . . C18 C 0.7419(2) 0.13243(14) 0.48473(19) 0.0332(4) Uani 1 1 d . . . H18A H 0.7591 0.1036 0.4018 0.050 Uiso 1 1 calc R . . H18B H 0.6232 0.1414 0.4626 0.050 Uiso 1 1 calc R . . H18C H 0.7885 0.0747 0.5612 0.050 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 0.0212(5) 0.0231(5) 0.0162(4) -0.0010(4) 0.0057(4) 0.0014(4) O2 0.0307(6) 0.0334(5) 0.0228(5) -0.0086(5) 0.0071(4) 0.0045(5) O3 0.0177(5) 0.0314(5) 0.0234(5) -0.0026(4) 0.0064(4) -0.0004(4) O4 0.0290(6) 0.0305(5) 0.0189(5) 0.0048(4) 0.0096(4) 0.0025(5) C1 0.0249(7) 0.0173(6) 0.0163(6) -0.0015(5) 0.0067(6) -0.0017(5) C2 0.0231(7) 0.0212(7) 0.0184(7) -0.0006(5) 0.0079(6) -0.0013(6) C3 0.0195(7) 0.0227(6) 0.0180(6) -0.0013(5) 0.0063(6) 0.0000(5) C4 0.0203(7) 0.0226(7) 0.0175(7) -0.0005(5) 0.0068(6) -0.0006(5) C5 0.0234(7) 0.0230(7) 0.0183(6) 0.0010(5) 0.0069(6) -0.0011(6) C6 0.0252(7) 0.0205(7) 0.0206(7) 0.0009(5) 0.0057(6) -0.0016(6) C7 0.0251(8) 0.0217(7) 0.0213(7) 0.0011(5) 0.0074(6) -0.0038(6) C8 0.0216(7) 0.0256(7) 0.0178(7) -0.0014(6) 0.0044(6) -0.0024(6) C9 0.0234(7) 0.0240(7) 0.0173(7) 0.0000(5) 0.0069(6) -0.0021(6) C10 0.0221(7) 0.0232(7) 0.0184(7) 0.0014(5) 0.0051(6) 0.0018(5) C11 0.0204(7) 0.0234(7) 0.0180(7) -0.0004(5) 0.0063(6) 0.0027(5) C12 0.0302(8) 0.0315(7) 0.0311(8) 0.0046(7) 0.0116(7) -0.0072(7) C13 0.0207(8) 0.0417(9) 0.0255(8) -0.0028(7) 0.0056(6) -0.0046(6) C14 0.0291(8) 0.0283(7) 0.0184(7) -0.0004(6) 0.0064(6) -0.0032(6) C15 0.0303(8) 0.0237(7) 0.0300(8) -0.0019(6) 0.0085(7) -0.0013(6) C16 0.0309(8) 0.0257(7) 0.0179(7) -0.0006(6) 0.0044(6) -0.0005(6) C17 0.0292(8) 0.0243(7) 0.0247(7) 0.0055(6) 0.0111(6) 0.0058(6) C18 0.0403(9) 0.0246(8) 0.0401(9) 0.0059(7) 0.0213(8) 0.0034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3336(17) . ? O1 C11 1.4649(17) . ? O2 C1 1.2120(17) . ? O3 C13 1.4159(19) . ? O3 C3 1.4345(16) . ? O4 C7 1.4196(17) . ? O4 H4 0.89(2) . ? C1 C2 1.504(2) . ? C2 C12 1.536(2) . ? C2 C3 1.5392(19) . ? C2 H2 1.0000 . ? C3 C4 1.5373(18) . ? C3 H3 1.0000 . ? C4 C14 1.5303(19) . ? C4 C5 1.5354(19) . ? C4 H4A 1.0000 . ? C5 C6 1.5411(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C15 1.530(2) . ? C6 C7 1.548(2) . ? C6 H6 1.0000 . ? C7 C8 1.502(2) . ? C7 H7 1.0000 . ? C8 C9 1.323(2) . ? C8 H8 0.9500 . ? C9 C10 1.506(2) . ? C9 H9 0.9500 . ? C10 C16 1.5265(19) . ? C10 C11 1.535(2) . ? C10 H10 1.0000 . ? C11 C17 1.514(2) . ? C11 H11 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.518(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C1 O1 C11 118.60(10) . . ? C13 O3 C3 114.98(11) . . ? C7 O4 H4 110.0(14) . . ? O2 C1 O1 123.76(13) . . ? O2 C1 C2 124.31(13) . . ? O1 C1 C2 111.91(11) . . ? C1 C2 C12 108.56(12) . . ? C1 C2 C3 110.88(11) . . ? C12 C2 C3 111.40(12) . . ? C1 C2 H2 108.6 . . ? C12 C2 H2 108.6 . . ? C3 C2 H2 108.6 . . ? O3 C3 C4 109.80(11) . . ? O3 C3 C2 107.15(10) . . ? C4 C3 C2 114.67(11) . . ? O3 C3 H3 108.3 . . ? C4 C3 H3 108.3 . . ? C2 C3 H3 108.3 . . ? C14 C4 C5 111.86(12) . . ? C14 C4 C3 109.32(12) . . ? C5 C4 C3 111.92(10) . . ? C14 C4 H4A 107.9 . . ? C5 C4 H4A 107.9 . . ? C3 C4 H4A 107.9 . . ? C4 C5 C6 116.98(11) . . ? C4 C5 H5A 108.1 . . ? C6 C5 H5A 108.1 . . ? C4 C5 H5B 108.1 . . ? C6 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C15 C6 C5 109.46(11) . . ? C15 C6 C7 110.28(12) . . ? C5 C6 C7 114.05(11) . . ? C15 C6 H6 107.6 . . ? C5 C6 H6 107.6 . . ? C7 C6 H6 107.6 . . ? O4 C7 C8 108.50(11) . . ? O4 C7 C6 112.97(12) . . ? C8 C7 C6 112.60(11) . . ? O4 C7 H7 107.5 . . ? C8 C7 H7 107.5 . . ? C6 C7 H7 107.5 . . ? C9 C8 C7 125.48(13) . . ? C9 C8 H8 117.3 . . ? C7 C8 H8 117.3 . . ? C8 C9 C10 126.39(13) . . ? C8 C9 H9 116.8 . . ? C10 C9 H9 116.8 . . ? C9 C10 C16 114.39(12) . . ? C9 C10 C11 108.51(12) . . ? C16 C10 C11 112.52(11) . . ? C9 C10 H10 107.0 . . ? C16 C10 H10 107.0 . . ? C11 C10 H10 107.0 . . ? O1 C11 C17 107.87(11) . . ? O1 C11 C10 106.35(11) . . ? C17 C11 C10 115.64(12) . . ? O1 C11 H11 108.9 . . ? C17 C11 H11 108.9 . . ? C10 C11 H11 108.9 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C6 C15 H15A 109.5 . . ? C6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 C18 113.21(13) . . ? C11 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? C11 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C11 O1 C1 O2 6.12(19) . . . . ? C11 O1 C1 C2 -175.36(11) . . . . ? O2 C1 C2 C12 76.29(17) . . . . ? O1 C1 C2 C12 -102.22(13) . . . . ? O2 C1 C2 C3 -46.39(18) . . . . ? O1 C1 C2 C3 135.10(11) . . . . ? C13 O3 C3 C4 114.95(13) . . . . ? C13 O3 C3 C2 -119.92(13) . . . . ? C1 C2 C3 O3 -176.88(11) . . . . ? C12 C2 C3 O3 62.10(15) . . . . ? C1 C2 C3 C4 -54.75(15) . . . . ? C12 C2 C3 C4 -175.77(12) . . . . ? O3 C3 C4 C14 -67.17(14) . . . . ? C2 C3 C4 C14 172.14(11) . . . . ? O3 C3 C4 C5 57.33(15) . . . . ? C2 C3 C4 C5 -63.36(15) . . . . ? C14 C4 C5 C6 -61.86(16) . . . . ? C3 C4 C5 C6 175.07(12) . . . . ? C4 C5 C6 C15 174.36(13) . . . . ? C4 C5 C6 C7 -61.56(16) . . . . ? C15 C6 C7 O4 -160.78(11) . . . . ? C5 C6 C7 O4 75.59(14) . . . . ? C15 C6 C7 C8 75.87(14) . . . . ? C5 C6 C7 C8 -47.76(16) . . . . ? O4 C7 C8 C9 2.77(19) . . . . ? C6 C7 C8 C9 128.58(15) . . . . ? C7 C8 C9 C10 -176.18(14) . . . . ? C8 C9 C10 C16 -8.7(2) . . . . ? C8 C9 C10 C11 117.85(15) . . . . ? C1 O1 C11 C17 -115.77(12) . . . . ? C1 O1 C11 C10 119.59(12) . . . . ? C9 C10 C11 O1 -61.30(13) . . . . ? C16 C10 C11 O1 66.31(14) . . . . ? C9 C10 C11 C17 178.99(12) . . . . ? C16 C10 C11 C17 -53.40(16) . . . . ? O1 C11 C17 C18 69.15(15) . . . . ? C10 C11 C17 C18 -171.97(12) . . . . ? 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 O4 H4 O2 0.89(2) 1.91(2) 2.8069(15) 177(2) 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.312 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.031