data_shelxl _audit_creation_method SHELXL-97 _publ_section_references ; CrystalClear, Rigaku Corp., (1999) Altomare, A., M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo A. Guagliardi, A. Moliterni, G. Polidori & R. Spagna. (1999) J. Appl. Cryst. 32, 115-119. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 O4' _chemical_formula_weight 390.46 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 ' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.631(3) _cell_length_b 6.1265(13) _cell_length_c 13.649(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.167(5) _cell_angle_gamma 90.00 _cell_volume 1056.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7678 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method 'phi and omega rotations' _diffrn_reflns_number 4760 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2967 _reflns_number_gt 2538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalClear (Rigaku, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0407P)^2^+0.1112P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _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 1.6(14) _refine_ls_number_reflns 2967 _refine_ls_number_parameters 266 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1932(2) 0.5140(5) 0.56527(19) 0.0309(7) Uani 1 1 d . . . C2 C 0.2235(2) 0.7517(5) 0.57106(18) 0.0289(6) Uani 1 1 d . . . C3 C 0.1200(2) 0.8712(5) 0.53987(18) 0.0329(7) Uani 1 1 d . . . H3A H 0.0606 0.8190 0.5773 0.044 Uiso 1 1 calc R . . H3B H 0.1269 1.0276 0.5493 0.044 Uiso 1 1 calc R . . C4 C 0.10488(19) 0.8154(5) 0.42985(19) 0.0305(7) Uani 1 1 d . . . H4A H 0.0380 0.7420 0.4170 0.041 Uiso 1 1 calc R . . H4B H 0.1089 0.9448 0.3892 0.041 Uiso 1 1 calc R . . C5 C 0.19884(19) 0.6632(4) 0.41402(18) 0.0248(6) Uani 1 1 d . . . C6 C 0.29050(18) 0.7670(5) 0.47617(17) 0.0249(6) Uani 1 1 d . . . C7 C 0.2735(2) 0.8255(5) 0.66706(19) 0.0408(8) Uani 1 1 d . . . H7A H 0.2258 0.7972 0.7194 0.061 Uiso 1 1 calc R . . H7B H 0.2882 0.9790 0.6640 0.061 Uiso 1 1 calc R . . H7C H 0.3384 0.7470 0.6787 0.061 Uiso 1 1 calc R . . C8 C 0.39050(19) 0.6233(5) 0.4797(2) 0.0355(7) Uani 1 1 d . . . H8A H 0.4209 0.6181 0.4159 0.053 Uiso 1 1 calc R . . H8B H 0.3720 0.4783 0.4998 0.053 Uiso 1 1 calc R . . H8C H 0.4410 0.6838 0.5257 0.053 Uiso 1 1 calc R . . C9 C 0.3211(2) 0.9980(5) 0.44860(19) 0.0318(7) Uani 1 1 d . . . H9A H 0.3658 1.0589 0.4993 0.048 Uiso 1 1 calc R . . H9B H 0.2583 1.0853 0.4410 0.048 Uiso 1 1 calc R . . H9C H 0.3584 0.9959 0.3881 0.048 Uiso 1 1 calc R . . C10 C 0.22437(19) 0.5988(5) 0.31080(19) 0.0276(6) Uani 1 1 d . . . C11 C 0.2660(2) 0.7544(5) 0.15504(17) 0.0311(7) Uani 1 1 d . . . H11 H 0.2237 0.6383 0.1241 0.041 Uiso 1 1 calc R . . C12 C 0.3830(2) 0.7013(5) 0.14900(18) 0.0295(7) Uani 1 1 d . . . C13 C 0.4585(2) 0.8482(6) 0.18547(19) 0.0408(8) Uani 1 1 d . . . H13 H 0.4371 0.9785 0.2139 0.054 Uiso 1 1 calc R . . C14 C 0.5659(2) 0.7993(6) 0.1793(2) 0.0494(9) Uani 1 1 d . . . H14 H 0.6161 0.8962 0.2046 0.066 Uiso 1 1 calc R . . C15 C 0.5980(2) 0.6076(7) 0.1359(2) 0.0453(8) Uani 1 1 d . . . H15 H 0.6698 0.5761 0.1313 0.060 Uiso 1 1 calc R . . C16 C 0.5235(2) 0.4629(6) 0.0993(2) 0.0421(8) Uani 1 1 d . . . H16 H 0.5450 0.3342 0.0696 0.056 Uiso 1 1 calc R . . C17 C 0.4168(2) 0.5092(5) 0.10668(19) 0.0347(7) Uani 1 1 d . . . H17 H 0.3670 0.4096 0.0828 0.046 Uiso 1 1 calc R . . C18 C 0.2378(2) 0.9703(5) 0.11066(19) 0.0355(7) Uani 1 1 d . . . H18 H 0.2606 1.0926 0.1455 0.047 Uiso 1 1 calc R . . C19 C 0.1841(2) 1.0093(6) 0.0274(2) 0.0374(7) Uani 1 1 d . . . H19 H 0.1721 1.1559 0.0132 0.050 Uiso 1 1 calc R . . C20 C 0.1412(2) 0.8544(5) -0.04505(19) 0.0355(7) Uani 1 1 d . . . C21 C 0.0472(2) 0.9079(6) -0.0960(2) 0.0462(9) Uani 1 1 d . . . H21 H 0.0148 1.0414 -0.0842 0.061 Uiso 1 1 calc R . . C22 C 0.0020(2) 0.7668(7) -0.1632(2) 0.0505(9) Uani 1 1 d . . . H22 H -0.0608 0.8050 -0.1955 0.067 Uiso 1 1 calc R . . C23 C 0.0492(2) 0.5689(6) -0.1829(2) 0.0476(10) Uani 1 1 d . . . H23 H 0.0178 0.4728 -0.2275 0.063 Uiso 1 1 calc R . . C24 C 0.1434(2) 0.5149(6) -0.13593(19) 0.0407(8) Uani 1 1 d . . . H24 H 0.1765 0.3832 -0.1498 0.054 Uiso 1 1 calc R . . C25 C 0.1887(2) 0.6571(5) -0.06801(18) 0.0345(8) Uani 1 1 d . . . H25 H 0.2524 0.6193 -0.0371 0.046 Uiso 1 1 calc R . . O1 O 0.17530(13) 0.4639(3) 0.46868(12) 0.0287(5) Uani 1 1 d . . . O2 O 0.18163(16) 0.3805(4) 0.62859(14) 0.0450(6) Uani 1 1 d . . . O3 O 0.23622(13) 0.7811(3) 0.25758(12) 0.0310(5) Uani 1 1 d . . . O4 O 0.23316(15) 0.4161(3) 0.28016(13) 0.0374(5) 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 0.0390(16) 0.0243(18) 0.0295(15) -0.0022(14) 0.0055(11) -0.0014(14) C2 0.0372(15) 0.0222(17) 0.0273(14) 0.0006(13) 0.0018(11) -0.0003(13) C3 0.0357(15) 0.0233(18) 0.0400(16) -0.0033(14) 0.0098(11) 0.0018(14) C4 0.0253(13) 0.0264(18) 0.0397(15) 0.0016(14) -0.0002(11) 0.0016(13) C5 0.0279(13) 0.0194(17) 0.0270(13) 0.0014(12) 0.0014(10) -0.0024(12) C6 0.0255(13) 0.0223(15) 0.0269(13) -0.0007(13) 0.0013(10) 0.0004(13) C7 0.0582(19) 0.032(2) 0.0322(16) -0.0030(14) -0.0005(13) -0.0046(16) C8 0.0297(15) 0.0300(18) 0.0467(18) -0.0003(15) -0.0025(12) 0.0041(14) C9 0.0311(14) 0.0262(17) 0.0382(16) -0.0008(14) 0.0006(11) -0.0050(14) C10 0.0256(14) 0.0246(18) 0.0325(15) -0.0016(14) -0.0022(10) -0.0017(13) C11 0.0436(16) 0.0278(18) 0.0221(14) -0.0020(13) 0.0029(11) 0.0017(14) C12 0.0394(15) 0.0273(18) 0.0218(13) 0.0015(12) 0.0041(11) 0.0007(13) C13 0.0463(18) 0.040(2) 0.0362(16) -0.0060(15) 0.0077(12) -0.0073(16) C14 0.0402(17) 0.060(3) 0.0484(19) -0.0092(19) 0.0051(13) -0.0119(17) C15 0.0390(17) 0.058(2) 0.0388(18) 0.0008(17) 0.0033(13) 0.0055(18) C16 0.0518(19) 0.039(2) 0.0361(16) 0.0031(15) 0.0067(13) 0.0103(17) C17 0.0437(17) 0.0289(19) 0.0314(15) -0.0030(14) 0.0008(12) 0.0003(15) C18 0.0457(16) 0.0290(19) 0.0322(16) 0.0008(14) 0.0085(12) -0.0023(14) C19 0.0443(16) 0.0312(18) 0.0370(16) 0.0067(15) 0.0103(12) 0.0020(15) C20 0.0337(15) 0.042(2) 0.0311(15) 0.0101(15) 0.0065(11) 0.0027(15) C21 0.0377(17) 0.055(3) 0.0462(18) 0.0109(18) 0.0025(13) 0.0059(17) C22 0.0322(16) 0.071(3) 0.0485(19) 0.014(2) -0.0036(13) -0.0014(19) C23 0.0425(18) 0.064(3) 0.0356(17) 0.0064(17) -0.0021(13) -0.0094(18) C24 0.0466(18) 0.043(2) 0.0325(16) 0.0001(16) 0.0042(13) 0.0022(16) C25 0.0327(15) 0.048(2) 0.0235(14) 0.0046(15) 0.0020(11) -0.0018(15) O1 0.0391(10) 0.0173(12) 0.0298(10) -0.0016(8) 0.0035(7) -0.0043(9) O2 0.0757(15) 0.0260(13) 0.0336(11) 0.0046(10) 0.0112(10) -0.0033(11) O3 0.0426(11) 0.0223(12) 0.0283(10) -0.0007(9) 0.0071(8) -0.0005(10) O4 0.0544(13) 0.0261(13) 0.0319(11) -0.0042(10) 0.0024(9) -0.0044(10) 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 O2 1.201(3) . ? C1 O1 1.368(3) . ? C1 C2 1.508(4) . ? C2 C7 1.512(4) . ? C2 C3 1.551(4) . ? C2 C6 1.564(3) . ? C3 C4 1.548(4) . ? C4 C5 1.528(3) . ? C5 O1 1.465(3) . ? C5 C10 1.504(3) . ? C5 C6 1.557(3) . ? C6 C9 1.516(4) . ? C6 C8 1.540(4) . ? C10 O4 1.201(3) . ? C10 O3 1.343(3) . ? C11 O3 1.466(3) . ? C11 C18 1.495(4) . ? C11 C12 1.517(4) . ? C12 C17 1.382(4) . ? C12 C13 1.395(4) . ? C13 C14 1.394(4) . ? C14 C15 1.381(5) . ? C15 C16 1.379(4) . ? C16 C17 1.383(4) . ? C18 C19 1.333(4) . ? C19 C20 1.467(4) . ? C20 C25 1.389(4) . ? C20 C21 1.402(4) . ? C21 C22 1.376(5) . ? C22 C23 1.380(5) . ? C23 C24 1.381(4) . ? C24 C25 1.387(4) . ? 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 O2 C1 O1 121.4(3) . . ? O2 C1 C2 130.9(3) . . ? O1 C1 C2 107.7(2) . . ? C1 C2 C7 115.8(2) . . ? C1 C2 C3 103.3(2) . . ? C7 C2 C3 115.6(2) . . ? C1 C2 C6 99.0(2) . . ? C7 C2 C6 118.4(2) . . ? C3 C2 C6 102.22(19) . . ? C4 C3 C2 104.4(2) . . ? C5 C4 C3 101.0(2) . . ? O1 C5 C10 107.9(2) . . ? O1 C5 C4 105.68(19) . . ? C10 C5 C4 118.3(2) . . ? O1 C5 C6 102.68(19) . . ? C10 C5 C6 116.50(19) . . ? C4 C5 C6 104.2(2) . . ? C9 C6 C8 109.2(2) . . ? C9 C6 C5 115.9(2) . . ? C8 C6 C5 112.6(2) . . ? C9 C6 C2 114.0(2) . . ? C8 C6 C2 113.4(2) . . ? C5 C6 C2 91.03(18) . . ? O4 C10 O3 125.1(2) . . ? O4 C10 C5 126.4(3) . . ? O3 C10 C5 108.5(2) . . ? O3 C11 C18 102.9(2) . . ? O3 C11 C12 110.2(2) . . ? C18 C11 C12 113.1(2) . . ? C17 C12 C13 118.9(3) . . ? C17 C12 C11 121.0(3) . . ? C13 C12 C11 120.1(3) . . ? C14 C13 C12 119.9(3) . . ? C15 C14 C13 120.2(3) . . ? C16 C15 C14 119.9(3) . . ? C15 C16 C17 120.0(3) . . ? C16 C17 C12 121.0(3) . . ? C19 C18 C11 128.1(3) . . ? C18 C19 C20 129.3(3) . . ? C25 C20 C21 117.2(3) . . ? C25 C20 C19 124.1(3) . . ? C21 C20 C19 118.7(3) . . ? C22 C21 C20 121.3(3) . . ? C21 C22 C23 120.5(3) . . ? C22 C23 C24 119.4(3) . . ? C23 C24 C25 120.0(3) . . ? C24 C25 C20 121.5(3) . . ? C1 O1 C5 105.8(2) . . ? C10 O3 C11 117.2(2) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.164 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.041