data_YL_9_90naph _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 O3' _chemical_formula_sum 'C22 H24 O3' _chemical_formula_weight 336.41 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) _chemical_absolute_configuration AD loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.8529(9) _cell_length_b 6.2316(6) _cell_length_c 16.8666(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.238(7) _cell_angle_gamma 90.00 _cell_volume 909.35(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2259 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 69.04 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7841 _exptl_absorpt_correction_T_max 0.9780 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 5846 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 69.05 _reflns_number_total 2672 _reflns_number_gt 2466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0510P)^2^+0.0900P] 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 0.0(3) _refine_ls_number_reflns 2672 _refine_ls_number_parameters 226 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 C1 C -0.5652(3) -0.6270(4) -0.12150(15) 0.0392(5) Uani 1 1 d . . . H1A H -0.6164 -0.5697 -0.1752 0.047 Uiso 1 1 calc R . . H1B H -0.5328 -0.5058 -0.0838 0.047 Uiso 1 1 calc R . . C2 C -0.6736(3) -0.7823(5) -0.08806(16) 0.0466(6) Uani 1 1 d . . . H2A H -0.6729 -0.7488 -0.0306 0.056 Uiso 1 1 calc R . . H2B H -0.7809 -0.7692 -0.1198 0.056 Uiso 1 1 calc R . . C3 C -0.6117(3) -1.0103(4) -0.09575(15) 0.0456(6) Uani 1 1 d . . . H3A H -0.6032 -1.0913 -0.0445 0.055 Uiso 1 1 calc R . . H3B H -0.6795 -1.0904 -0.1402 0.055 Uiso 1 1 calc R . . C4 C -0.4552(3) -0.9716(4) -0.11429(14) 0.0408(5) Uani 1 1 d . . . H4A H -0.3825 -1.0826 -0.1160 0.049 Uiso 1 1 calc R . . C5 C -0.4290(3) -0.7668(4) -0.12799(14) 0.0345(5) Uani 1 1 d . . . C6 C -0.2823(3) -0.6783(4) -0.14573(14) 0.0348(5) Uani 1 1 d . . . H6A H -0.2144 -0.7997 -0.1552 0.042 Uiso 1 1 calc R . . C7 C -0.3082(3) -0.5264(3) -0.21928(14) 0.0335(5) Uani 1 1 d . . . H7A H -0.3630 -0.3955 -0.2056 0.040 Uiso 1 1 calc R . . C8 C -0.1556(3) -0.4573(4) -0.23743(13) 0.0353(5) Uani 1 1 d . . . H8A H -0.0950 -0.5631 -0.2568 0.042 Uiso 1 1 calc R . . C9 C -0.1007(3) -0.2601(4) -0.22823(14) 0.0373(5) Uani 1 1 d . . . H9A H -0.1519 -0.1571 -0.2018 0.045 Uiso 1 1 calc R . . C10 C 0.0380(3) -0.1946(4) -0.25783(14) 0.0364(5) Uani 1 1 d . . . C11 C 0.1682(3) 0.1093(4) -0.29571(16) 0.0462(6) Uani 1 1 d . . . H11A H 0.1666 0.2663 -0.2927 0.069 Uiso 1 1 calc R . . H11B H 0.1492 0.0646 -0.3527 0.069 Uiso 1 1 calc R . . H11C H 0.2695 0.0563 -0.2673 0.069 Uiso 1 1 calc R . . C12 C -0.4073(3) -0.6287(4) -0.29491(14) 0.0339(5) Uani 1 1 d . . . C13 C -0.5390(3) -0.5334(4) -0.33537(14) 0.0372(5) Uani 1 1 d . . . H13A H -0.5687 -0.3995 -0.3164 0.045 Uiso 1 1 calc R . . C14 C -0.6346(3) -0.6287(4) -0.40598(14) 0.0353(5) Uani 1 1 d . . . C15 C -0.7726(3) -0.5334(4) -0.44803(16) 0.0440(6) Uani 1 1 d . . . H15A H -0.8032 -0.3975 -0.4313 0.053 Uiso 1 1 calc R . . C16 C -0.8623(3) -0.6349(5) -0.51250(16) 0.0502(7) Uani 1 1 d . . . H16A H -0.9554 -0.5691 -0.5402 0.060 Uiso 1 1 calc R . . C17 C -0.8195(3) -0.8360(5) -0.53892(16) 0.0465(6) Uani 1 1 d . . . H17A H -0.8844 -0.9045 -0.5839 0.056 Uiso 1 1 calc R . . C18 C -0.6871(3) -0.9328(4) -0.50101(15) 0.0421(6) Uani 1 1 d . . . H18A H -0.6588 -1.0676 -0.5198 0.051 Uiso 1 1 calc R . . C19 C -0.5888(3) -0.8311(4) -0.43204(14) 0.0366(5) Uani 1 1 d . . . C20 C -0.4506(3) -0.9258(4) -0.39103(15) 0.0399(6) Uani 1 1 d . . . H20A H -0.4184 -1.0592 -0.4091 0.048 Uiso 1 1 calc R . . C21 C -0.3615(3) -0.8259(4) -0.32473(15) 0.0399(6) Uani 1 1 d . . . H21A H -0.2671 -0.8903 -0.2982 0.048 Uiso 1 1 calc R . . C22 C -0.1155(3) -0.6830(5) -0.01495(16) 0.0490(6) Uani 1 1 d . . . H22A H -0.0643 -0.5913 0.0300 0.073 Uiso 1 1 calc R . . H22B H -0.0374 -0.7635 -0.0361 0.073 Uiso 1 1 calc R . . H22C H -0.1847 -0.7835 0.0045 0.073 Uiso 1 1 calc R . . O1 O 0.1266(2) -0.3112(3) -0.28126(12) 0.0477(5) Uani 1 1 d . . . O2 O 0.04868(19) 0.0215(3) -0.25783(11) 0.0425(4) Uani 1 1 d . . . O3 O -0.20293(18) -0.5528(3) -0.07794(10) 0.0387(4) 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 C1 0.0383(15) 0.0421(12) 0.0388(12) -0.0024(10) 0.0115(10) -0.0020(10) C2 0.0415(16) 0.0594(16) 0.0418(14) -0.0050(12) 0.0156(11) -0.0088(12) C3 0.0474(16) 0.0525(15) 0.0364(13) 0.0053(11) 0.0079(11) -0.0167(12) C4 0.0459(15) 0.0420(13) 0.0355(12) -0.0017(10) 0.0110(10) -0.0049(11) C5 0.0380(14) 0.0357(11) 0.0308(11) -0.0031(9) 0.0094(9) -0.0052(9) C6 0.0347(14) 0.0333(11) 0.0373(12) -0.0035(9) 0.0095(9) -0.0013(9) C7 0.0325(13) 0.0308(11) 0.0393(12) 0.0008(9) 0.0124(10) -0.0011(9) C8 0.0326(13) 0.0392(12) 0.0352(11) 0.0000(9) 0.0098(9) 0.0005(9) C9 0.0366(14) 0.0373(12) 0.0402(12) 0.0000(10) 0.0131(10) 0.0000(10) C10 0.0336(13) 0.0396(12) 0.0357(12) -0.0026(10) 0.0068(10) -0.0050(10) C11 0.0458(16) 0.0475(13) 0.0477(14) 0.0029(12) 0.0153(11) -0.0155(11) C12 0.0293(14) 0.0369(12) 0.0381(12) 0.0024(10) 0.0133(9) -0.0040(9) C13 0.0390(14) 0.0350(12) 0.0420(13) 0.0001(10) 0.0185(10) -0.0016(9) C14 0.0306(14) 0.0380(12) 0.0410(12) 0.0038(10) 0.0160(10) -0.0008(9) C15 0.0408(15) 0.0489(14) 0.0450(14) 0.0057(11) 0.0152(11) 0.0060(11) C16 0.0435(17) 0.0670(17) 0.0419(14) 0.0052(13) 0.0132(11) 0.0013(13) C17 0.0380(16) 0.0659(17) 0.0369(12) -0.0028(12) 0.0107(10) -0.0073(12) C18 0.0384(15) 0.0531(14) 0.0371(12) -0.0024(11) 0.0133(10) -0.0064(11) C19 0.0301(14) 0.0421(13) 0.0408(13) 0.0031(10) 0.0146(10) -0.0031(9) C20 0.0450(16) 0.0347(12) 0.0425(13) -0.0033(10) 0.0148(11) 0.0038(10) C21 0.0384(16) 0.0384(13) 0.0437(13) 0.0016(10) 0.0107(11) 0.0031(10) C22 0.0393(16) 0.0577(16) 0.0475(15) 0.0007(12) 0.0040(11) 0.0022(12) O1 0.0414(11) 0.0451(9) 0.0617(11) -0.0048(9) 0.0221(9) -0.0050(8) O2 0.0396(10) 0.0372(9) 0.0538(10) 0.0020(8) 0.0167(8) -0.0073(7) O3 0.0350(9) 0.0411(9) 0.0387(9) -0.0025(7) 0.0050(7) -0.0036(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 C1 C5 1.510(3) . ? C1 C2 1.551(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.538(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.503(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.326(3) . ? C4 H4A 0.9500 . ? C5 C6 1.499(3) . ? C6 O3 1.439(3) . ? C6 C7 1.538(3) . ? C6 H6A 1.0000 . ? C7 C8 1.510(3) . ? C7 C12 1.526(3) . ? C7 H7A 1.0000 . ? C8 C9 1.318(3) . ? C8 H8A 0.9500 . ? C9 C10 1.478(3) . ? C9 H9A 0.9500 . ? C10 O1 1.196(3) . ? C10 O2 1.350(3) . ? C11 O2 1.454(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.356(3) . ? C12 C21 1.419(3) . ? C13 C14 1.436(3) . ? C13 H13A 0.9500 . ? C14 C15 1.408(3) . ? C14 C19 1.423(3) . ? C15 C16 1.359(4) . ? C15 H15A 0.9500 . ? C16 C17 1.409(4) . ? C16 H16A 0.9500 . ? C17 C18 1.352(4) . ? C17 H17A 0.9500 . ? C18 C19 1.443(3) . ? C18 H18A 0.9500 . ? C19 C20 1.402(3) . ? C20 C21 1.373(3) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 O3 1.427(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 C5 C1 C2 103.4(2) . . ? C5 C1 H1A 111.1 . . ? C2 C1 H1A 111.1 . . ? C5 C1 H1B 111.1 . . ? C2 C1 H1B 111.1 . . ? H1A C1 H1B 109.0 . . ? C3 C2 C1 106.67(19) . . ? C3 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? C3 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? C4 C3 C2 103.28(19) . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3B 111.1 . . ? C2 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C5 C4 C3 113.2(2) . . ? C5 C4 H4A 123.4 . . ? C3 C4 H4A 123.4 . . ? C4 C5 C6 125.5(2) . . ? C4 C5 C1 111.8(2) . . ? C6 C5 C1 122.8(2) . . ? O3 C6 C5 109.83(17) . . ? O3 C6 C7 105.71(17) . . ? C5 C6 C7 113.58(19) . . ? O3 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C8 C7 C12 109.28(17) . . ? C8 C7 C6 110.59(18) . . ? C12 C7 C6 112.22(17) . . ? C8 C7 H7A 108.2 . . ? C12 C7 H7A 108.2 . . ? C6 C7 H7A 108.2 . . ? C9 C8 C7 124.4(2) . . ? C9 C8 H8A 117.8 . . ? C7 C8 H8A 117.8 . . ? C8 C9 C10 122.0(2) . . ? C8 C9 H9A 119.0 . . ? C10 C9 H9A 119.0 . . ? O1 C10 O2 123.7(2) . . ? O1 C10 C9 126.4(2) . . ? O2 C10 C9 109.81(19) . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C21 118.7(2) . . ? C13 C12 C7 121.2(2) . . ? C21 C12 C7 120.1(2) . . ? C12 C13 C14 121.9(2) . . ? C12 C13 H13A 119.0 . . ? C14 C13 H13A 119.0 . . ? C15 C14 C19 119.5(2) . . ? C15 C14 C13 122.7(2) . . ? C19 C14 C13 117.8(2) . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C15 C16 C17 121.1(3) . . ? C15 C16 H16A 119.5 . . ? C17 C16 H16A 119.5 . . ? C18 C17 C16 120.8(3) . . ? C18 C17 H17A 119.6 . . ? C16 C17 H17A 119.6 . . ? C17 C18 C19 120.0(2) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C20 C19 C14 119.8(2) . . ? C20 C19 C18 121.8(2) . . ? C14 C19 C18 118.4(2) . . ? C21 C20 C19 120.1(2) . . ? C21 C20 H20A 120.0 . . ? C19 C20 H20A 120.0 . . ? C20 C21 C12 121.6(2) . . ? C20 C21 H21A 119.2 . . ? C12 C21 H21A 119.2 . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C10 O2 C11 115.64(19) . . ? C22 O3 C6 112.29(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C1 C2 C3 -12.6(3) . . . . ? C1 C2 C3 C4 12.4(3) . . . . ? C2 C3 C4 C5 -7.9(3) . . . . ? C3 C4 C5 C6 178.2(2) . . . . ? C3 C4 C5 C1 -0.2(3) . . . . ? C2 C1 C5 C4 8.2(3) . . . . ? C2 C1 C5 C6 -170.3(2) . . . . ? C4 C5 C6 O3 -109.9(3) . . . . ? C1 C5 C6 O3 68.4(3) . . . . ? C4 C5 C6 C7 131.9(3) . . . . ? C1 C5 C6 C7 -49.8(3) . . . . ? O3 C6 C7 C8 63.9(2) . . . . ? C5 C6 C7 C8 -175.60(19) . . . . ? O3 C6 C7 C12 -173.76(17) . . . . ? C5 C6 C7 C12 -53.3(2) . . . . ? C12 C7 C8 C9 123.8(3) . . . . ? C6 C7 C8 C9 -112.2(3) . . . . ? C7 C8 C9 C10 -171.1(2) . . . . ? C8 C9 C10 O1 -11.6(4) . . . . ? C8 C9 C10 O2 166.0(2) . . . . ? C8 C7 C12 C13 -112.8(2) . . . . ? C6 C7 C12 C13 124.2(2) . . . . ? C8 C7 C12 C21 66.5(2) . . . . ? C6 C7 C12 C21 -56.6(2) . . . . ? C21 C12 C13 C14 1.6(3) . . . . ? C7 C12 C13 C14 -179.16(17) . . . . ? C12 C13 C14 C15 179.1(2) . . . . ? C12 C13 C14 C19 1.2(3) . . . . ? C19 C14 C15 C16 0.7(3) . . . . ? C13 C14 C15 C16 -177.2(2) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C16 C17 C18 C19 0.8(3) . . . . ? C15 C14 C19 C20 179.2(2) . . . . ? C13 C14 C19 C20 -2.8(3) . . . . ? C15 C14 C19 C18 -0.4(3) . . . . ? C13 C14 C19 C18 177.60(19) . . . . ? C17 C18 C19 C20 -179.9(2) . . . . ? C17 C18 C19 C14 -0.3(3) . . . . ? C14 C19 C20 C21 1.6(3) . . . . ? C18 C19 C20 C21 -178.8(2) . . . . ? C19 C20 C21 C12 1.3(3) . . . . ? C13 C12 C21 C20 -2.9(3) . . . . ? C7 C12 C21 C20 177.8(2) . . . . ? O1 C10 O2 C11 5.6(4) . . . . ? C9 C10 O2 C11 -172.1(2) . . . . ? C5 C6 O3 C22 81.4(2) . . . . ? C7 C6 O3 C22 -155.71(17) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 69.05 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.186 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.032