data_dec206 _audit_creation_date 2006-12-05T19:10:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H32 O5' _chemical_formula_sum 'C21 H32 O5' _chemical_formula_weight 364.47 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.2709(4) _cell_length_b 17.9596(10) _cell_length_c 18.5642(12) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2090.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8101 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 22.986 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.268946E-1 _diffrn_orient_matrix_ub_12 -0.464527E-1 _diffrn_orient_matrix_ub_13 -0.282763E-1 _diffrn_orient_matrix_ub_21 0.104888 _diffrn_orient_matrix_ub_22 0.273891E-1 _diffrn_orient_matrix_ub_23 -0.307286E-1 _diffrn_orient_matrix_ub_31 0.117068 _diffrn_orient_matrix_ub_32 -0.138676E-1 _diffrn_orient_matrix_ub_33 0.340275E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.2009 _diffrn_reflns_av_unetI/netI 0.0909 _diffrn_reflns_number 8934 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 23.07 _diffrn_reflns_theta_full 23.07 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 1697 _reflns_number_gt 1339 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The H atoms on O were refined; other H atoms were in riding mode. 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^)+(0.1177P)^2^+0.6909P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.019(7) _refine_ls_number_reflns 1697 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.2048 _refine_ls_wR_factor_gt 0.173 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(3) _refine_diff_density_max 0.389 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.8766(7) 0.2286(2) 0.27987(19) 0.0520(12) Uani 1 1 d . . . O2 O 1.0395(6) 0.1374(3) 0.2181(2) 0.0511(12) Uani 1 1 d . . . O3 O 0.4566(7) 0.2177(3) 0.1898(2) 0.0577(13) Uani 1 1 d . . . O4 O 0.3076(6) 0.1401(3) 0.0809(2) 0.0552(14) Uani 1 1 d . . . H4X H 0.248(13) 0.136(5) 0.114(4) 0.07(3) Uiso 1 1 d . . . O5 O 0.5713(8) 0.2439(3) 0.0052(2) 0.0638(15) Uani 1 1 d . . . H5X H 0.657(13) 0.267(4) -0.018(4) 0.07(3) Uiso 1 1 d . . . C1 C 0.9251(9) 0.1908(4) 0.2202(3) 0.0401(14) Uani 1 1 d . . . C2 C 0.8206(9) 0.2242(4) 0.1547(3) 0.0435(15) Uani 1 1 d . . . H2 H 0.9009 0.2069 0.1112 0.052 Uiso 1 1 calc R . . C3 C 0.5893(10) 0.1962(3) 0.1480(3) 0.0423(14) Uani 1 1 d . . . C4 C 0.5321(9) 0.1421(4) 0.0878(3) 0.0441(15) Uani 1 1 d . . . C5 C 0.6258(10) 0.0643(4) 0.1045(3) 0.0544(18) Uani 1 1 d . . . H5A H 0.6219 0.0345 0.0597 0.065 Uiso 1 1 calc R . . H5B H 0.7775 0.0707 0.1179 0.065 Uiso 1 1 calc R . . C6 C 0.5165(10) 0.0196(4) 0.1639(3) 0.0517(17) Uani 1 1 d . . . C7 C 0.6016(10) 0.0159(4) 0.2283(3) 0.0486(15) Uani 1 1 d . . . H7 H 0.7321 0.0416 0.2357 0.058 Uiso 1 1 calc R . . C8 C 0.5104(12) -0.0253(4) 0.2911(4) 0.0629(19) Uani 1 1 d . . . H8 H 0.411 -0.0639 0.2714 0.075 Uiso 1 1 calc R . . C9 C 0.3828(12) 0.0233(5) 0.3421(4) 0.082(3) Uani 1 1 d . . . H9A H 0.2845 -0.0091 0.3697 0.098 Uiso 1 1 calc R . . H9B H 0.2942 0.0576 0.313 0.098 Uiso 1 1 calc R . . C10 C 0.5119(12) 0.0700(5) 0.3960(4) 0.073(2) Uani 1 1 d . . . C11 C 0.6481(12) 0.1279(4) 0.3653(4) 0.063(2) Uani 1 1 d . . . H11 H 0.5897 0.1538 0.3253 0.076 Uiso 1 1 calc R . . C12 C 0.8377(11) 0.1490(5) 0.3848(3) 0.061(2) Uani 1 1 d . . . C13 C 0.9714(11) 0.2041(4) 0.3478(3) 0.0572(18) Uani 1 1 d . . . H13 H 1.1129 0.1808 0.3373 0.069 Uiso 1 1 calc R . . C14 C 1.0090(14) 0.2763(5) 0.3895(3) 0.079(2) Uani 1 1 d . . . H14A H 0.8719 0.3032 0.3946 0.095 Uiso 1 1 calc R . . H14B H 1.061 0.2642 0.4385 0.095 Uiso 1 1 calc R . . C15 C 1.169(2) 0.3265(7) 0.3528(5) 0.136(5) Uani 1 1 d . . . H15A H 1.3104 0.3037 0.3551 0.204 Uiso 1 1 calc R . . H15B H 1.1714 0.3749 0.3771 0.204 Uiso 1 1 calc R . . H15C H 1.1275 0.3334 0.3023 0.204 Uiso 1 1 calc R . . C16 C 0.8259(13) 0.3089(4) 0.1555(3) 0.0639(19) Uani 1 1 d . . . H16A H 0.7517 0.3272 0.1985 0.096 Uiso 1 1 calc R . . H16B H 0.755 0.3281 0.1123 0.096 Uiso 1 1 calc R . . H16C H 0.9743 0.326 0.1563 0.096 Uiso 1 1 calc R . . C17 C 0.6202(10) 0.1681(4) 0.0155(3) 0.0529(17) Uani 1 1 d . . . H17A H 0.7767 0.161 0.0144 0.063 Uiso 1 1 calc R . . H17B H 0.5568 0.1382 -0.0238 0.063 Uiso 1 1 calc R . . C18 C 0.3182(13) -0.0196(4) 0.1417(4) 0.069(2) Uani 1 1 d . . . H18A H 0.3179 -0.07 0.1619 0.104 Uiso 1 1 calc R . . H18B H 0.3121 -0.0225 0.089 0.104 Uiso 1 1 calc R . . H18C H 0.1939 0.0078 0.1596 0.104 Uiso 1 1 calc R . . C19 C 0.6863(17) -0.0667(6) 0.3333(5) 0.105(3) Uani 1 1 d . . . H19A H 0.7532 -0.1039 0.302 0.158 Uiso 1 1 calc R . . H19B H 0.6233 -0.0915 0.3752 0.158 Uiso 1 1 calc R . . H19C H 0.7942 -0.0309 0.3494 0.158 Uiso 1 1 calc R . . C20 C 0.5007(17) 0.0540(7) 0.4663(4) 0.106(3) Uani 1 1 d . . . H20A H 0.5848 0.0811 0.4999 0.127 Uiso 1 1 calc R . . H20B H 0.4085 0.0156 0.4827 0.127 Uiso 1 1 calc R . . C21 C 0.9548(14) 0.1152(6) 0.4509(4) 0.091(3) Uani 1 1 d . . . H21A H 0.9217 0.1446 0.4939 0.136 Uiso 1 1 calc R . . H21B H 1.109 0.116 0.4423 0.136 Uiso 1 1 calc R . . H21C H 0.9077 0.0637 0.458 0.136 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 0.066(3) 0.058(3) 0.0322(19) -0.002(2) -0.001(2) 0.007(2) O2 0.036(2) 0.071(3) 0.046(2) -0.004(2) 0.0043(19) 0.003(2) O3 0.048(2) 0.073(3) 0.053(2) -0.008(2) 0.018(2) 0.008(2) O4 0.027(2) 0.095(4) 0.043(2) 0.004(3) -0.002(2) 0.000(2) O5 0.047(3) 0.100(5) 0.045(2) 0.024(2) -0.001(2) -0.002(3) C1 0.033(3) 0.050(4) 0.037(3) -0.007(3) 0.006(3) -0.002(3) C2 0.044(3) 0.055(4) 0.032(3) -0.002(3) 0.007(3) 0.001(3) C3 0.046(3) 0.050(4) 0.031(3) 0.003(3) 0.003(3) 0.007(3) C4 0.034(3) 0.064(4) 0.035(3) -0.002(3) 0.000(3) 0.003(3) C5 0.048(4) 0.075(5) 0.041(3) -0.013(3) 0.006(3) -0.001(3) C6 0.043(3) 0.050(4) 0.061(4) -0.009(3) -0.005(3) 0.006(3) C7 0.046(3) 0.044(4) 0.056(4) -0.006(3) -0.004(3) 0.007(3) C8 0.067(4) 0.057(4) 0.064(4) 0.005(4) -0.006(4) 0.002(3) C9 0.055(4) 0.092(6) 0.098(6) 0.033(5) 0.016(5) 0.006(4) C10 0.059(5) 0.103(7) 0.058(4) 0.008(4) 0.013(4) 0.010(4) C11 0.070(5) 0.070(5) 0.049(4) 0.007(4) 0.010(4) 0.011(4) C12 0.046(4) 0.107(6) 0.030(3) 0.002(4) 0.004(3) 0.002(4) C13 0.059(4) 0.080(5) 0.033(3) 0.004(3) -0.007(3) -0.002(4) C14 0.096(6) 0.101(6) 0.040(3) -0.012(4) -0.003(4) -0.020(5) C15 0.180(11) 0.146(11) 0.080(6) -0.010(6) 0.008(7) -0.093(9) C16 0.087(5) 0.055(4) 0.049(4) 0.002(3) -0.006(4) -0.008(4) C17 0.046(4) 0.074(5) 0.038(3) 0.002(3) -0.002(3) 0.005(3) C18 0.074(5) 0.068(5) 0.065(4) 0.000(4) -0.010(4) -0.020(4) C19 0.121(8) 0.107(8) 0.088(6) 0.028(5) -0.023(6) 0.039(6) C20 0.108(7) 0.153(10) 0.057(5) 0.006(5) 0.022(5) -0.037(7) C21 0.081(6) 0.126(8) 0.065(4) 0.018(5) -0.001(4) 0.013(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.334(7) . ? O1 C13 1.462(7) . ? O2 C1 1.200(7) . ? O3 C3 1.201(7) . ? O4 C4 1.414(7) . ? O4 H4X 0.73(7) . ? O5 C17 1.408(9) . ? O5 H5X 0.81(8) . ? C1 C2 1.505(8) . ? C2 C16 1.523(9) . ? C2 C3 1.540(9) . ? C2 H2 1 . ? C3 C4 1.524(8) . ? C4 C17 1.525(8) . ? C4 C5 1.547(9) . ? C5 C6 1.526(9) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.312(8) . ? C6 C18 1.487(10) . ? C7 C8 1.494(9) . ? C7 H7 0.95 . ? C8 C9 1.517(11) . ? C8 C19 1.544(11) . ? C8 H8 1 . ? C9 C10 1.536(12) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C20 1.338(11) . ? C10 C11 1.461(11) . ? C11 C12 1.300(10) . ? C11 H11 0.95 . ? C12 C13 1.467(10) . ? C12 C21 1.553(10) . ? C13 C14 1.529(11) . ? C13 H13 1 . ? C14 C15 1.509(13) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 H20A 0.95 . ? C20 H20B 0.95 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? 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 C13 118.1(5) . . ? C4 O4 H4X 116(6) . . ? C17 O5 H5X 116(6) . . ? O2 C1 O1 124.7(5) . . ? O2 C1 C2 123.5(5) . . ? O1 C1 C2 111.7(5) . . ? C1 C2 C16 112.3(5) . . ? C1 C2 C3 110.2(5) . . ? C16 C2 C3 110.3(5) . . ? C1 C2 H2 108 . . ? C16 C2 H2 108 . . ? C3 C2 H2 108 . . ? O3 C3 C4 121.0(5) . . ? O3 C3 C2 119.8(5) . . ? C4 C3 C2 119.2(5) . . ? O4 C4 C3 108.5(5) . . ? O4 C4 C17 106.8(5) . . ? C3 C4 C17 111.4(5) . . ? O4 C4 C5 111.9(6) . . ? C3 C4 C5 109.8(4) . . ? C17 C4 C5 108.4(5) . . ? C6 C5 C4 116.7(5) . . ? C6 C5 H5A 108.1 . . ? C4 C5 H5A 108.1 . . ? C6 C5 H5B 108.1 . . ? C4 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C7 C6 C18 124.6(6) . . ? C7 C6 C5 120.1(6) . . ? C18 C6 C5 115.2(6) . . ? C6 C7 C8 125.5(6) . . ? C6 C7 H7 117.3 . . ? C8 C7 H7 117.3 . . ? C7 C8 C9 113.8(6) . . ? C7 C8 C19 111.1(7) . . ? C9 C8 C19 109.7(6) . . ? C7 C8 H8 107.3 . . ? C9 C8 H8 107.3 . . ? C19 C8 H8 107.3 . . ? C8 C9 C10 116.3(6) . . ? C8 C9 H9A 108.2 . . ? C10 C9 H9A 108.2 . . ? C8 C9 H9B 108.2 . . ? C10 C9 H9B 108.2 . . ? H9A C9 H9B 107.4 . . ? C20 C10 C11 124.3(9) . . ? C20 C10 C9 119.4(9) . . ? C11 C10 C9 116.2(6) . . ? C12 C11 C10 129.3(7) . . ? C12 C11 H11 115.3 . . ? C10 C11 H11 115.3 . . ? C11 C12 C13 126.1(6) . . ? C11 C12 C21 122.6(7) . . ? C13 C12 C21 111.3(6) . . ? O1 C13 C12 112.0(5) . . ? O1 C13 C14 104.1(6) . . ? C12 C13 C14 115.1(5) . . ? O1 C13 H13 108.5 . . ? C12 C13 H13 108.5 . . ? C14 C13 H13 108.5 . . ? C15 C14 C13 112.4(7) . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C2 C16 H16A 109.5 . . ? C2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O5 C17 C4 109.7(5) . . ? O5 C17 H17A 109.7 . . ? C4 C17 H17A 109.7 . . ? O5 C17 H17B 109.7 . . ? C4 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C6 C18 H18A 109.5 . . ? C6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 C19 H19A 109.5 . . ? C8 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C8 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C10 C20 H20A 120 . . ? C10 C20 H20B 120 . . ? H20A C20 H20B 120 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? #===END