Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Roger Bishop' 'Donald C. Craig' 'K. Harris' 'Kazunori Nakano' 'Marcia Scudder' 'Weimin Yue.' _publ_contact_author_name 'Roger Bishop' _publ_contact_author_address ; School of Chemistry University of New South Wales Sydney NSW 2052 AUSTRALIA ; _publ_contact_author_email R.BISHOP@UNSW.EDU.AU _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Alternative hydrogen bonding modes employed by a helical tubuland diol host molecule ; # Attachment 'drb112.cif' data_drb112 _database_code_depnum_ccdc_archive 'CCDC 295343' _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1996. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al,1994)' _computing_structure_refinement 'RAELS, (Rae, 1996)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C15 H26 O2, 0.25(C6 H6)' _chemical_formula_sum 'C16.5 H27.5 O2' _chemical_formula_iupac ? _chemical_formula_weight 257.9 _chemical_absolute_configuration ? # CRYSTAL DATA _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 31 2 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -y,x-y,1/3+z 3 y-x,-x,2/3+z 4 y,x,-z 5 -x,y-x,1/3-z 6 x-y,-y,2/3-z _cell_length_a 13.773(2) _cell_length_b 13.773(2) _cell_length_c 6.998(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1149.6(4) _cell_formula_units_Z 3 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _cell_measurement_temperature 294 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.12 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 427.5 _exptl_absorpt_coefficient_mu 0.551 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.93 # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 1681 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_max 70 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 70 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 0 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 1462 _reflns_number_gt 1309 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_ref 0.067 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1309 _refine_ls_number_parameters 100 _refine_ls_goodness_of_fit_ref 1.68 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.003 _refine_diff_density_max 0.19 _refine_diff_density_min -0.19 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1 -0.2357(1) 0.3804(2) 0.2224(2) 0.0511(5) Uani O 1.0 C1 0.0000(2) 0.3218(3) 0.1667(0) 0.0481(7) Uani C 1.0 C2 -0.0983(2) 0.3374(2) 0.1122(3) 0.0416(5) Uani C 1.0 C3 -0.1427(2) 0.3691(2) 0.2882(3) 0.0416(5) Uani C 1.0 C4 -0.0506(2) 0.4765(2) 0.3895(3) 0.0428(5) Uani C 1.0 C5 0.0637(2) 0.4797(2) 0.3947(3) 0.0458(5) Uani C 1.0 C6 -0.1905(2) 0.2719(2) 0.4339(3) 0.0566(7) Uani C 1.0 C7 -0.0431(2) 0.5876(2) 0.3335(4) 0.0575(6) Uani C 1.0 C8 -0.0453(4) 0.6229(4) 0.1316(7) 0.053(1) Uani C 0.5 C9 -0.0475(6) 0.7320(6) 0.1263(13) 0.093(2) Uani C 0.5 C1Bz 0.0717(30) 0.0708(36) 0.0444(61) 0.167(9) Uani C 0.125 C2Bz 0.0403(27) -0.0045(44) -0.1077(49) 0.167(9) Uani C 0.125 C3Bz -0.0641(27) -0.1022(33) -0.1065(47) 0.167(9) Uani C 0.125 C4Bz -0.1371(17) -0.1247(21) 0.0466(53) 0.167(9) Uani C 0.125 C5Bz -0.1057(28) -0.0495(31) 0.1987(47) 0.167(9) Uani C 0.125 C6Bz -0.0013(38) 0.0483(30) 0.1975(54) 0.167(9) Uani C 0.125 H1O1 -0.2826 0.3815 0.3305 0.051 Uani H 1.0 H1C1 0.0211 0.2904 0.0557 0.048 Uani H 0.5 H2C1 -0.0212 0.2693 0.2776 0.048 Uani H 0.5 HC2 -0.1598 0.2626 0.0683 0.042 Uani H 1.0 HC4 -0.0749 0.4658 0.5262 0.043 Uani H 1.0 H1C5 0.0621 0.4345 0.5077 0.046 Uani H 1.0 H2C5 0.1231 0.5597 0.4134 0.046 Uani H 1.0 H1C6 -0.2193 0.2932 0.5482 0.057 Uani H 1.0 H2C6 -0.2532 0.2033 0.3736 0.057 Uani H 1.0 H3C6 -0.1301 0.2562 0.4742 0.057 Uani H 1.0 H1C7 0.0290 0.6477 0.3890 0.058 Uani H 0.5 H2C7 -0.1074 0.5880 0.3992 0.058 Uani H 0.5 H1'C7 -0.0341 0.6292 0.4554 0.058 Uani H 0.5 H2'C7 -0.1166 0.5678 0.2734 0.058 Uani H 0.5 HC8 -0.1184 0.5644 0.0766 0.053 Uani H 1.0 H1C9 -0.0489 0.7538 -0.0096 0.093 Uani H 0.5 H2C9 -0.1160 0.7218 0.1939 0.093 Uani H 0.5 H3C9 0.0209 0.7923 0.1910 0.093 Uani H 0.5 HC1Bz 0.1466 0.1409 0.0436 0.167 Uani H 0.125 HC2Bz 0.0927 0.0117 -0.2175 0.167 Uani H 0.125 HC3Bz -0.0866 -0.1562 -0.2156 0.167 Uani H 0.125 HC4Bz -0.2120 -0.1948 0.0474 0.167 Uani H 0.125 HC5Bz -0.1581 -0.0656 0.3085 0.167 Uani H 0.125 HC6Bz 0.0212 0.1022 0.3066 0.167 Uani H 0.125 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1 0.0414(9) 0.072(1) 0.0374(7) 0.0264(8) -0.0033(6) -0.0012(7) O C1 0.055(2) 0.051(1) 0.040(1) 0.0274(9) 0.005(1) 0.0025(7) C C2 0.042(1) 0.043(1) 0.0302(9) 0.0137(9) -0.0014(7) -0.0050(8) C C3 0.038(1) 0.052(1) 0.0285(8) 0.0182(9) 0.0014(7) 0.0017(8) C C4 0.043(1) 0.055(1) 0.0244(8) 0.0200(9) 0.0025(7) -0.0043(8) C C5 0.045(1) 0.064(1) 0.0222(8) 0.022(1) -0.0043(8) -0.0008(8) C C6 0.054(1) 0.064(2) 0.039(1) 0.020(1) 0.0074(9) 0.0099(9) C C7 0.052(1) 0.057(1) 0.061(1) 0.025(1) 0.008(1) -0.009(1) C C8 0.045(2) 0.049(3) 0.066(3) 0.023(2) 0.006(2) 0.008(2) C C9 0.105(6) 0.071(4) 0.117(6) 0.054(4) 0.021(5) 0.017(4) C C1Bz 0.134(9) 0.207(9) 0.156(9) 0.084(9) -0.016(9) 0.044(9) C C2Bz 0.134(9) 0.207(9) 0.156(9) 0.084(9) -0.016(9) 0.044(9) C C3Bz 0.134(9) 0.207(9) 0.156(9) 0.084(9) -0.016(9) 0.044(9) C C4Bz 0.134(9) 0.207(9) 0.156(9) 0.084(9) -0.016(9) 0.044(9) C C5Bz 0.134(9) 0.207(9) 0.156(9) 0.084(9) -0.016(9) 0.044(9) C C6Bz 0.134(9) 0.207(9) 0.156(9) 0.084(9) -0.016(9) 0.044(9) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.441(3) 1_555 1_555 no C1 C2 1.521(2) 1_555 1_555 no C1 C2 1.521(4) 1_555 5_555 no C2 C3 1.533(3) 1_555 1_555 no C2 C5 1.536(3) 1_555 5_555 no C3 C4 1.557(3) 1_555 1_555 no C3 C6 1.544(3) 1_555 1_555 no C4 C5 1.553(3) 1_555 1_555 no C4 C7 1.532(4) 1_555 1_555 no C5 C2 1.536(3) 1_555 5_555 no C7 C8 1.499(5) 1_555 1_555 no C7 C8 1.488(5) 1_555 5_555 no C8 C7 1.488(5) 1_555 5_555 no C8 C9 1.519(8) 1_555 1_555 no C1Bz C2Bz 1.395(9) 1_555 1_555 no C1Bz C6Bz 1.395(9) 1_555 1_555 no C2Bz C3Bz 1.395(9) 1_555 1_555 no C3Bz C4Bz 1.395(9) 1_555 1_555 no C4Bz C5Bz 1.395(9) 1_555 1_555 no C5Bz C6Bz 1.395(9) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 108.3(3) 1_555 1_555 5_555 no C1 C2 C3 110.4(1) 1_555 1_555 1_555 no C1 C2 C5 108.3(2) 1_555 1_555 5_555 no C3 C2 C5 117.5(2) 1_555 1_555 5_555 no O1 C3 C2 106.1(1) 1_555 1_555 1_555 no O1 C3 C4 112.9(2) 1_555 1_555 1_555 no O1 C3 C6 106.8(2) 1_555 1_555 1_555 no C2 C3 C4 112.6(2) 1_555 1_555 1_555 no C2 C3 C6 110.0(2) 1_555 1_555 1_555 no C4 C3 C6 108.4(2) 1_555 1_555 1_555 no C3 C4 C5 111.8(2) 1_555 1_555 1_555 no C3 C4 C7 116.7(2) 1_555 1_555 1_555 no C5 C4 C7 114.6(2) 1_555 1_555 1_555 no C2 C5 C4 118.7(2) 5_555 1_555 1_555 no C4 C7 C8 124.2(3) 1_555 1_555 1_555 no C4 C7 C8 121.7(2) 1_555 1_555 5_555 no C7 C8 C7 117.4(3) 1_555 1_555 5_555 no C7 C8 C9 110.9(5) 1_555 1_555 1_555 no C7 C8 C9 109.5(4) 5_555 1_555 1_555 no C2Bz C1Bz C6Bz 120.0 1_555 1_555 1_555 no C1Bz C2Bz C3Bz 120.0 1_555 1_555 1_555 no C2Bz C3Bz C4Bz 120.0 1_555 1_555 1_555 no C3Bz C4Bz C5Bz 120.0 1_555 1_555 1_555 no C4Bz C5Bz C6Bz 120.0 1_555 1_555 1_555 no C1Bz C6Bz C5Bz 120.0 1_555 1_555 1_555 no # Attachment 'drb128.cif' data_drb128 _database_code_depnum_ccdc_archive 'CCDC 295344' _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1996. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al,1994)' _computing_structure_refinement 'RAELS, (Rae, 1996)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C15 H26 O2, C2 H F3 O2' _chemical_formula_sum 'C17 H27 F3 O4' _chemical_formula_iupac ? _chemical_formula_weight 352.4 _chemical_absolute_configuration ? # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 7.328(2) _cell_length_b 13.460(2) _cell_length_c 19.037(4) _cell_angle_alpha 90 _cell_angle_beta 91.87(1) _cell_angle_gamma 90 _cell_volume 1876.7(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 20 _cell_measurement_theta_max 24 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.25 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752.0 _exptl_absorpt_coefficient_mu 0.912 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.89 # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 3024 _diffrn_reflns_av_R_equivalents 0.011 _diffrn_reflns_theta_max 60 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 60 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 32 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 2779 _reflns_number_gt 1812 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.116 _refine_ls_wR_factor_ref 0.173 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1812 _refine_ls_number_parameters 218 _refine_ls_goodness_of_fit_ref 2.22 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 1.26 _refine_diff_density_min -0.64 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1 0.4588(5) 0.4144(3) 0.3213(2) 0.066(1) Uani O 1.0 O2 0.2768(6) 0.7914(3) 0.2163(2) 0.075(1) Uani O 1.0 C1 0.3940(9) 0.6707(5) 0.3902(4) 0.074(2) Uani C 1.0 C2 0.3456(8) 0.5642(5) 0.3703(3) 0.065(2) Uani C 1.0 C3 0.5168(8) 0.5150(4) 0.3406(3) 0.061(2) Uani C 1.0 C4 0.5914(7) 0.5701(4) 0.2759(3) 0.061(2) Uani C 1.0 C5 0.5825(8) 0.6837(5) 0.2860(4) 0.074(2) Uani C 1.0 C6 0.4193(8) 0.7291(5) 0.3223(4) 0.067(2) Uani C 1.0 C7 0.2365(8) 0.7375(4) 0.2801(3) 0.062(2) Uani C 1.0 C8 0.1505(8) 0.6350(4) 0.2623(4) 0.065(2) Uani C 1.0 C9 0.1687(8) 0.5631(4) 0.3251(4) 0.068(2) Uani C 1.0 C10 0.6634(10) 0.5046(5) 0.3979(4) 0.080(2) Uani C 1.0 C11 0.1034(10) 0.7978(5) 0.3187(5) 0.083(2) Uani C 1.0 C12 0.5267(11) 0.5339(5) 0.2035(4) 0.084(2) Uani C 1.0 C13 0.3279(16) 0.5108(8) 0.1843(8) 0.072(5) Uani C 0.48 C13' 0.3750(18) 0.5838(11) 0.1608(6) 0.108(8) Uani C 0.52 C14 0.1927(11) 0.5904(5) 0.1909(4) 0.085(2) Uani C 1.0 C15 0.3082(41) 0.4778(17) 0.1067(9) 0.113(9) Uani C 0.48 C15' 0.3933(49) 0.5358(21) 0.0878(9) 0.145(9) Uani C 0.52 C1T 0.0842(9) 0.2340(7) 0.4662(4) 0.152(3) Uani C 1.0 F1T -0.0930(10) 0.2354(7) 0.4665(4) 0.213(3) Uani F 1.0 F3T 0.1405(12) 0.2650(8) 0.5277(4) 0.284(4) Uani F 1.0 F2T 0.1306(14) 0.1410(7) 0.4628(5) 0.261(5) Uani F 1.0 C2T 0.1564(10) 0.2939(6) 0.4084(4) 0.080(2) Uani C 1.0 O1T 0.0693(8) 0.3076(5) 0.3570(4) 0.109(2) Uani O 1.0 O2T 0.3231(7) 0.3190(4) 0.4190(3) 0.102(2) Uani O 1.0 H1O1 0.5580 0.3682 0.3072 0.066 Uani H 1.0 H1O2 0.1559 0.7971 0.1907 0.075 Uani H 1.0 H1C1 0.5097 0.6719 0.4195 0.074 Uani H 1.0 H2C1 0.2931 0.7008 0.4173 0.074 Uani H 1.0 HC2 0.3192 0.5286 0.4149 0.065 Uani H 1.0 HC4 0.7250 0.5549 0.2779 0.061 Uani H 1.0 H1C5 0.5860 0.7142 0.2381 0.074 Uani H 1.0 H2C5 0.6944 0.7034 0.3141 0.074 Uani H 1.0 HC6 0.4554 0.7981 0.3364 0.067 Uani H 1.0 HC8 0.0212 0.6412 0.2444 0.065 Uani H 1.0 H1C9 0.1536 0.4942 0.3060 0.068 Uani H 1.0 H2C9 0.0665 0.5782 0.3569 0.068 Uani H 1.0 H1C10 0.7071 0.5720 0.4128 0.080 Uani H 1.0 H2C10 0.6120 0.4695 0.4392 0.080 Uani H 1.0 H3C10 0.7679 0.4655 0.3798 0.080 Uani H 1.0 H1C11 0.0722 0.7629 0.3631 0.083 Uani H 1.0 H2C11 0.1580 0.8642 0.3303 0.083 Uani H 1.0 H3C11 -0.0099 0.8071 0.2887 0.083 Uani H 1.0 H1C12 0.5958 0.4712 0.1949 0.084 Uani H 0.48 H2C12 0.5649 0.5861 0.1696 0.084 Uani H 0.48 H1'C12 0.4870 0.4635 0.2100 0.084 Uani H 0.52 H2'C12 0.6365 0.5355 0.1737 0.084 Uani H 0.52 HC13 0.2893 0.4540 0.2142 0.072 Uani H 0.48 HC13' 0.4157 0.6542 0.1550 0.108 Uani H 0.52 H1C14 0.0748 0.5638 0.1709 0.085 Uani H 0.48 H2C14 0.2347 0.6466 0.1611 0.085 Uani H 0.48 H1'C14 0.1472 0.5205 0.1926 0.085 Uani H 0.52 H2'C14 0.1168 0.6291 0.1559 0.085 Uani H 0.52 H1C15 0.1771 0.4629 0.0948 0.113 Uani H 0.48 H2C15 0.3515 0.5323 0.0756 0.113 Uani H 0.48 H3C15 0.3833 0.4169 0.0995 0.113 Uani H 0.48 H1C15' 0.2981 0.5637 0.0546 0.145 Uani H 0.52 H2C15' 0.5172 0.5503 0.0698 0.145 Uani H 0.52 H3C15' 0.3765 0.4623 0.0917 0.145 Uani H 0.52 H1O2T 0.3775 0.3572 0.3798 0.102 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1 0.066(3) 0.054(2) 0.078(3) 0.001(2) 0.011(2) -0.005(2) O O2 0.064(3) 0.065(3) 0.096(4) -0.006(2) 0.010(2) 0.010(2) O C1 0.079(5) 0.068(4) 0.076(4) 0.004(3) 0.011(3) -0.013(4) C C2 0.061(4) 0.071(4) 0.064(4) 0.001(3) 0.014(3) -0.005(3) C C3 0.061(3) 0.056(4) 0.068(4) -0.002(3) 0.010(3) 0.001(3) C C4 0.047(3) 0.062(4) 0.075(4) 0.002(3) 0.013(3) 0.002(3) C C5 0.050(3) 0.069(4) 0.105(5) -0.013(3) 0.009(3) 0.001(4) C C6 0.057(4) 0.062(4) 0.081(4) -0.008(3) 0.001(3) -0.019(3) C C7 0.051(3) 0.054(3) 0.079(4) -0.003(3) 0.006(3) 0.002(3) C C8 0.050(3) 0.057(4) 0.088(5) -0.007(3) 0.003(3) -0.001(3) C C9 0.056(4) 0.060(4) 0.089(5) -0.008(3) 0.018(3) 0.002(3) C C10 0.076(4) 0.080(5) 0.084(5) 0.007(3) -0.008(4) -0.004(4) C C11 0.075(4) 0.070(4) 0.104(6) 0.010(3) 0.017(4) 0.000(4) C C12 0.101(6) 0.076(5) 0.078(5) 0.007(4) 0.029(4) 0.000(4) C C13 0.101(9) 0.048(8) 0.068(9) 0.013(8) -0.013(8) -0.006(7) C C13' 0.170(9) 0.089(9) 0.063(9) 0.044(9) -0.016(9) -0.024(9) C C14 0.091(5) 0.072(5) 0.092(6) -0.010(4) -0.015(4) -0.003(4) C C15 0.191(9) 0.085(9) 0.061(9) 0.012(9) -0.039(9) -0.012(9) C C15' 0.233(9) 0.130(9) 0.072(9) 0.070(9) 0.013(9) -0.002(9) C C1T 0.167(4) 0.191(6) 0.099(3) -0.101(4) 0.021(3) -0.009(4) C F1T 0.170(4) 0.345(7) 0.129(4) -0.131(5) 0.077(4) -0.034(4) F F3T 0.321(7) 0.442(9) 0.091(3) -0.261(7) 0.012(4) -0.005(4) F F2T 0.357(7) 0.188(6) 0.240(6) -0.053(6) 0.014(7) 0.106(4) F C2T 0.070(5) 0.091(5) 0.080(5) -0.029(4) 0.010(4) -0.014(4) C O1T 0.086(4) 0.128(5) 0.113(5) -0.033(3) -0.013(3) 0.016(4) O O2T 0.094(4) 0.127(5) 0.086(4) -0.023(3) -0.001(3) 0.027(3) O # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.463(7) 1_555 1_555 no O2 C7 1.453(7) 1_555 1_555 no C1 C2 1.522(9) 1_555 1_555 no C1 C6 1.529(10) 1_555 1_555 no C2 C3 1.542(8) 1_555 1_555 no C2 C9 1.532(9) 1_555 1_555 no C3 C4 1.551(8) 1_555 1_555 no C3 C10 1.513(9) 1_555 1_555 no C4 C5 1.543(9) 1_555 1_555 no C4 C12 1.523(10) 1_555 1_555 no C5 C6 1.529(9) 1_555 1_555 no C6 C7 1.544(8) 1_555 1_555 no C7 C8 1.550(8) 1_555 1_555 no C7 C11 1.482(9) 1_555 1_555 no C8 C9 1.541(9) 1_555 1_555 no C8 C14 1.527(10) 1_555 1_555 no C12 C13 1.522(13) 1_555 1_555 no C12 C13' 1.514(13) 1_555 1_555 no C13 C14 1.467(13) 1_555 1_555 no C13 C15 1.545(15) 1_555 1_555 no C13' C14 1.473(13) 1_555 1_555 no C13' C15' 1.541(15) 1_555 1_555 no C1T F1T 1.299(5) 1_555 1_555 no C1T F3T 1.299(6) 1_555 1_555 no C1T F2T 1.299(5) 1_555 1_555 no C1T C2T 1.476(13) 1_555 1_555 no C2T O1T 1.165(9) 1_555 1_555 no C2T O2T 1.277(8) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 107.9(5) 1_555 1_555 1_555 no C1 C2 C3 108.1(5) 1_555 1_555 1_555 no C1 C2 C9 109.6(5) 1_555 1_555 1_555 no C3 C2 C9 118.3(5) 1_555 1_555 1_555 no O1 C3 C2 104.9(5) 1_555 1_555 1_555 no O1 C3 C4 110.5(5) 1_555 1_555 1_555 no O1 C3 C10 106.8(5) 1_555 1_555 1_555 no C2 C3 C4 113.4(5) 1_555 1_555 1_555 no C2 C3 C10 110.0(5) 1_555 1_555 1_555 no C4 C3 C10 110.9(5) 1_555 1_555 1_555 no C3 C4 C5 111.0(5) 1_555 1_555 1_555 no C3 C4 C12 117.2(5) 1_555 1_555 1_555 no C5 C4 C12 114.6(6) 1_555 1_555 1_555 no C4 C5 C6 119.3(5) 1_555 1_555 1_555 no C1 C6 C5 107.2(5) 1_555 1_555 1_555 no C1 C6 C7 110.5(5) 1_555 1_555 1_555 no C5 C6 C7 118.2(6) 1_555 1_555 1_555 no O2 C7 C6 106.0(5) 1_555 1_555 1_555 no O2 C7 C8 110.8(5) 1_555 1_555 1_555 no O2 C7 C11 107.2(5) 1_555 1_555 1_555 no C6 C7 C8 112.8(5) 1_555 1_555 1_555 no C6 C7 C11 110.9(6) 1_555 1_555 1_555 no C8 C7 C11 109.0(5) 1_555 1_555 1_555 no C7 C8 C9 111.5(5) 1_555 1_555 1_555 no C7 C8 C14 116.8(5) 1_555 1_555 1_555 no C9 C8 C14 115.4(5) 1_555 1_555 1_555 no C2 C9 C8 118.7(5) 1_555 1_555 1_555 no C4 C12 C13 123.3(7) 1_555 1_555 1_555 no C4 C12 C13' 123.1(7) 1_555 1_555 1_555 no C12 C13 C14 118.3(7) 1_555 1_555 1_555 no C12 C13 C15 110.3(14) 1_555 1_555 1_555 no C14 C13 C15 104.5(13) 1_555 1_555 1_555 no C12 C13' C14 118.5(8) 1_555 1_555 1_555 no C12 C13' C15' 102.4(12) 1_555 1_555 1_555 no C14 C13' C15' 118.9(17) 1_555 1_555 1_555 no C8 C14 C13 121.3(8) 1_555 1_555 1_555 no C8 C14 C13' 125.7(7) 1_555 1_555 1_555 no F1T C1T F3T 106.2(6) 1_555 1_555 1_555 no F1T C1T F2T 106.2(6) 1_555 1_555 1_555 no F1T C1T C2T 112.2(7) 1_555 1_555 1_555 no F3T C1T F2T 106.2(6) 1_555 1_555 1_555 no F3T C1T C2T 112.7(7) 1_555 1_555 1_555 no F2T C1T C2T 112.9(7) 1_555 1_555 1_555 no C1T C2T O1T 120.8(7) 1_555 1_555 1_555 no C1T C2T O2T 113.0(7) 1_555 1_555 1_555 no O1T C2T O2T 125.9(8) 1_555 1_555 1_555 no 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 C6 C1 C2 C3 70.2(7) 1_555 1_555 1_555 1_555 no C6 C1 C2 C9 -60.0(6) 1_555 1_555 1_555 1_555 no C2 C1 C6 C5 -63.8(7) 1_555 1_555 1_555 1_555 no C2 C1 C6 C7 66.2(6) 1_555 1_555 1_555 1_555 no C1 C2 C3 O1 -178.8(5) 1_555 1_555 1_555 1_555 no C1 C2 C3 C4 -58.1(7) 1_555 1_555 1_555 1_555 no C1 C2 C3 C10 66.7(7) 1_555 1_555 1_555 1_555 no C9 C2 C3 O1 -53.6(7) 1_555 1_555 1_555 1_555 no C9 C2 C3 C4 67.1(7) 1_555 1_555 1_555 1_555 no C9 C2 C3 C10 -168.1(5) 1_555 1_555 1_555 1_555 no C1 C2 C9 C8 48.7(7) 1_555 1_555 1_555 1_555 no C3 C2 C9 C8 -75.7(7) 1_555 1_555 1_555 1_555 no O1 C3 C4 C5 157.9(5) 1_555 1_555 1_555 1_555 no O1 C3 C4 C12 23.6(7) 1_555 1_555 1_555 1_555 no C2 C3 C4 C5 40.5(7) 1_555 1_555 1_555 1_555 no C2 C3 C4 C12 -93.8(7) 1_555 1_555 1_555 1_555 no C10 C3 C4 C5 -83.9(6) 1_555 1_555 1_555 1_555 no C10 C3 C4 C12 141.9(6) 1_555 1_555 1_555 1_555 no C3 C4 C5 C6 -37.7(8) 1_555 1_555 1_555 1_555 no C12 C4 C5 C6 97.9(7) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13 45.8(9) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13' 99.0(9) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13 -86.9(8) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13' -33.7(10) 1_555 1_555 1_555 1_555 no C4 C5 C6 C1 49.4(8) 1_555 1_555 1_555 1_555 no C4 C5 C6 C7 -76.2(8) 1_555 1_555 1_555 1_555 no C1 C6 C7 O2 -178.5(4) 1_555 1_555 1_555 1_555 no C1 C6 C7 C8 -57.1(7) 1_555 1_555 1_555 1_555 no C1 C6 C7 C11 65.6(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 O2 -54.5(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 C8 66.8(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 C11 -170.5(6) 1_555 1_555 1_555 1_555 no O2 C7 C8 C9 160.0(5) 1_555 1_555 1_555 1_555 no O2 C7 C8 C14 24.3(7) 1_555 1_555 1_555 1_555 no C6 C7 C8 C9 41.3(7) 1_555 1_555 1_555 1_555 no C6 C7 C8 C14 -94.3(7) 1_555 1_555 1_555 1_555 no C11 C7 C8 C9 -82.3(6) 1_555 1_555 1_555 1_555 no C11 C7 C8 C14 142.0(6) 1_555 1_555 1_555 1_555 no C7 C8 C9 C2 -38.7(7) 1_555 1_555 1_555 1_555 no C14 C8 C9 C2 97.7(7) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13 102.3(9) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13' 47.3(10) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13 -31.6(9) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13' -86.7(9) 1_555 1_555 1_555 1_555 no C4 C12 C13 C14 58.8(14) 1_555 1_555 1_555 1_555 no C4 C12 C13 C15 179.0(11) 1_555 1_555 1_555 1_555 no C4 C12 C13' C14 -59.6(14) 1_555 1_555 1_555 1_555 no C4 C12 C13' C15' 167.5(15) 1_555 1_555 1_555 1_555 no C12 C13 C14 C8 -64.8(13) 1_555 1_555 1_555 1_555 no C15 C13 C14 C8 172.1(13) 1_555 1_555 1_555 1_555 no C12 C13' C14 C8 54.4(14) 1_555 1_555 1_555 1_555 no C15' C13' C14 C8 179.7(13) 1_555 1_555 1_555 1_555 no F1T C1T C2T O1T -26.4(10) 1_555 1_555 1_555 1_555 no F1T C1T C2T O2T 159.6(6) 1_555 1_555 1_555 1_555 no F3T C1T C2T O1T -146.2(8) 1_555 1_555 1_555 1_555 no F3T C1T C2T O2T 39.8(8) 1_555 1_555 1_555 1_555 no F2T C1T C2T O1T 93.6(9) 1_555 1_555 1_555 1_555 no F2T C1T C2T O2T -80.5(7) 1_555 1_555 1_555 1_555 no # Attachment 'drb130.cif' data_drb130 _database_code_depnum_ccdc_archive 'CCDC 295345' _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, 1014. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1996. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al,1994)' _computing_structure_refinement 'RAELS, (Rae, 1996)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H32 O3' _chemical_formula_iupac ? _chemical_formula_weight 284.4 _chemical_absolute_configuration ? # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 7.037(2) _cell_length_b 13.661(2) _cell_length_c 18.194(5) _cell_angle_alpha 90 _cell_angle_beta 107.19(1) _cell_angle_gamma 90 _cell_volume 1670.9(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 20 _cell_measurement_theta_max 23 _cell_measurement_temperature 294 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.13 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632.0 _exptl_absorpt_coefficient_mu 0.590 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(DeMeulenaer & Tompa, 1965)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.94 # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 2704 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_theta_max 60 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 60 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 8 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 2477 _reflns_number_gt 1997 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.060 _refine_ls_wR_factor_ref 0.106 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1997 _refine_ls_number_parameters 201 _refine_ls_goodness_of_fit_ref 1.89 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.002 _refine_diff_density_max 0.34 _refine_diff_density_min -0.25 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1 0.6480(3) 0.3086(1) 0.3270(1) 0.0609(6) Uani O 1.0 O2 0.7025(3) 0.6909(1) 0.2174(1) 0.0685(6) Uani O 1.0 C1 0.7628(5) 0.5625(2) 0.4045(2) 0.0711(9) Uani C 1.0 C2 0.7995(4) 0.4582(2) 0.3804(2) 0.0611(8) Uani C 1.0 C3 0.6009(4) 0.4055(2) 0.3490(2) 0.0545(7) Uani C 1.0 C4 0.4545(4) 0.4594(2) 0.2802(2) 0.0544(7) Uani C 1.0 C5 0.4617(4) 0.5721(2) 0.2917(2) 0.0631(8) Uani C 1.0 C6 0.6627(4) 0.6208(2) 0.3318(2) 0.0602(8) Uani C 1.0 C7 0.8076(4) 0.6355(2) 0.2845(2) 0.0574(7) Uani C 1.0 C8 0.8900(4) 0.5382(2) 0.2628(2) 0.0585(8) Uani C 1.0 C9 0.9392(4) 0.4650(2) 0.3294(2) 0.0632(8) Uani C 1.0 C10 0.5023(5) 0.3903(2) 0.4128(2) 0.0719(9) Uani C 1.0 C11 0.9819(5) 0.7000(2) 0.3283(2) 0.079(1) Uani C 1.0 C12 0.4509(4) 0.4256(2) 0.1993(2) 0.0630(8) Uani C 1.0 C13 0.6343(6) 0.4105(3) 0.1748(2) 0.060(2) Uani C 0.70 C13' 0.5569(7) 0.4836(6) 0.1536(4) 0.070(4) Uani C 0.30 C14 0.7765(5) 0.4937(2) 0.1833(2) 0.0738(9) Uani C 1.0 C15 0.5714(9) 0.3711(5) 0.0920(3) 0.081(2) Uani C 0.70 C15' 0.5214(23) 0.4345(12) 0.0747(6) 0.095(4) Uani C 0.30 O1Et 1.0141(3) 0.2147(2) 0.3633(1) 0.0833(8) Uani O 1.0 C1Et 1.0749(7) 0.1989(3) 0.4420(3) 0.111(1) Uani C 1.0 C2Et 0.9409(11) 0.1363(6) 0.4659(4) 0.178(3) Uani C 1.0 H1O1 0.5252 0.2674 0.3114 0.061 Uani H 1.0 H1O2 0.8029 0.6993 0.1888 0.068 Uani H 1.0 H1C1 0.8923 0.5938 0.4327 0.071 Uani H 1.0 H2C1 0.6743 0.5605 0.4385 0.071 Uani H 1.0 HC2 0.8745 0.4229 0.4284 0.061 Uani H 1.0 HC4 0.3203 0.4406 0.2839 0.054 Uani H 1.0 H1C5 0.3700 0.5882 0.3228 0.063 Uani H 1.0 H2C5 0.4104 0.6024 0.2396 0.063 Uani H 1.0 HC6 0.6328 0.6872 0.3487 0.060 Uani H 1.0 HC8 1.0043 0.5487 0.2416 0.058 Uani H 1.0 H1C9 1.0743 0.4822 0.3638 0.063 Uani H 1.0 H2C9 0.9432 0.3986 0.3067 0.063 Uani H 1.0 H1C10 0.4665 0.4553 0.4302 0.072 Uani H 1.0 H2C10 0.3792 0.3500 0.3926 0.072 Uani H 1.0 H3C10 0.5968 0.3557 0.4571 0.072 Uani H 1.0 H1C11 1.0612 0.6653 0.3758 0.079 Uani H 1.0 H2C11 1.0686 0.7141 0.2948 0.079 Uani H 1.0 H3C11 0.9299 0.7629 0.3428 0.079 Uani H 1.0 H1C12 0.3696 0.4753 0.1631 0.063 Uani H 0.70 H2C12 0.3796 0.3614 0.1911 0.063 Uani H 0.70 H1'C12 0.3079 0.4227 0.1680 0.063 Uani H 0.30 H2'C12 0.5090 0.3583 0.2049 0.063 Uani H 0.30 HC13 0.7102 0.3565 0.2078 0.060 Uani H 0.70 HC13' 0.4975 0.5507 0.1454 0.070 Uani H 0.30 H1C14 0.6990 0.5487 0.1522 0.074 Uani H 0.70 H2C14 0.8807 0.4714 0.1598 0.074 Uani H 0.70 H1'C14 0.8155 0.5344 0.1444 0.074 Uani H 0.30 H2'C14 0.8304 0.4260 0.1835 0.074 Uani H 0.30 H1C15 0.6922 0.3606 0.0747 0.081 Uani H 0.70 H2C15 0.4995 0.3076 0.0901 0.081 Uani H 0.70 H3C15 0.4816 0.4195 0.0572 0.081 Uani H 0.70 H1C15' 0.5914 0.4724 0.0435 0.095 Uani H 0.30 H2C15' 0.5741 0.3661 0.0820 0.095 Uani H 0.30 H3C15' 0.3755 0.4331 0.0474 0.095 Uani H 0.30 H1O1Et 0.8822 0.2485 0.3502 0.083 Uani H 1.0 H1C1Et 1.0824 0.2634 0.4688 0.111 Uani H 1.0 H2C1Et 1.2096 0.1679 0.4567 0.111 Uani H 1.0 H1C2Et 0.9903 0.1269 0.5229 0.178 Uani H 1.0 H2C2Et 0.8058 0.1669 0.4518 0.178 Uani H 1.0 H3C2Et 0.9330 0.0714 0.4397 0.178 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1 0.052(1) 0.042(1) 0.089(1) 0.0041(7) 0.021(1) 0.0024(8) O O2 0.057(1) 0.051(1) 0.100(2) 0.0049(8) 0.027(1) 0.0129(9) O C1 0.072(2) 0.059(2) 0.078(2) -0.007(1) 0.016(2) -0.012(1) C C2 0.049(2) 0.052(2) 0.073(2) 0.001(1) 0.005(1) 0.004(1) C C3 0.047(2) 0.046(1) 0.070(2) 0.002(1) 0.016(1) -0.002(1) C C4 0.039(1) 0.047(1) 0.078(2) 0.001(1) 0.017(1) 0.003(1) C C5 0.046(2) 0.051(2) 0.096(2) 0.007(1) 0.027(1) 0.001(1) C C6 0.057(2) 0.043(1) 0.081(2) 0.004(1) 0.021(1) -0.009(1) C C7 0.042(1) 0.041(1) 0.086(2) 0.001(1) 0.014(1) -0.002(1) C C8 0.040(1) 0.046(1) 0.092(2) -0.001(1) 0.025(1) -0.002(1) C C9 0.038(1) 0.049(2) 0.098(2) 0.005(1) 0.014(1) 0.003(1) C C10 0.069(2) 0.071(2) 0.080(2) 0.000(1) 0.028(2) 0.006(2) C C11 0.060(2) 0.050(2) 0.122(3) -0.009(1) 0.018(2) -0.011(2) C C12 0.056(2) 0.055(2) 0.072(2) -0.006(1) 0.011(1) 0.001(1) C C13 0.063(3) 0.056(3) 0.062(3) -0.008(2) 0.021(2) -0.005(2) C C13' 0.091(8) 0.044(6) 0.077(7) -0.009(5) 0.027(6) 0.003(5) C C14 0.084(2) 0.056(2) 0.090(2) -0.011(2) 0.041(2) -0.011(1) C C15 0.096(4) 0.081(4) 0.070(3) -0.019(3) 0.029(3) -0.009(3) C C15' 0.115(9) 0.080(9) 0.080(8) -0.017(8) 0.014(7) 0.007(7) C O1Et 0.076(2) 0.086(2) 0.093(2) 0.030(1) 0.032(1) 0.018(1) O C1Et 0.105(3) 0.101(3) 0.113(3) 0.016(2) 0.014(3) 0.007(2) C C2Et 0.203(6) 0.187(6) 0.166(5) 0.059(5) 0.090(5) 0.082(5) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.449(3) 1_555 1_555 no O2 C7 1.441(3) 1_555 1_555 no C1 C2 1.536(4) 1_555 1_555 no C1 C6 1.526(4) 1_555 1_555 no C2 C3 1.525(4) 1_555 1_555 no C2 C9 1.542(4) 1_555 1_555 no C3 C4 1.552(4) 1_555 1_555 no C3 C10 1.531(4) 1_555 1_555 no C4 C5 1.553(3) 1_555 1_555 no C4 C12 1.535(4) 1_555 1_555 no C5 C6 1.538(4) 1_555 1_555 no C6 C7 1.529(4) 1_555 1_555 no C7 C8 1.547(3) 1_555 1_555 no C7 C11 1.529(4) 1_555 1_555 no C8 C9 1.529(4) 1_555 1_555 no C8 C14 1.553(4) 1_555 1_555 no C12 C13 1.499(5) 1_555 1_555 no C12 C13' 1.497(5) 1_555 1_555 no C13 C14 1.492(4) 1_555 1_555 no C13 C15 1.537(5) 1_555 1_555 no C13' C14 1.485(5) 1_555 1_555 no C13' C15' 1.537(7) 1_555 1_555 no O1Et C1Et 1.385(5) 1_555 1_555 no C1Et C2Et 1.433(8) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 108.1(2) 1_555 1_555 1_555 no C1 C2 C3 109.4(2) 1_555 1_555 1_555 no C1 C2 C9 107.8(2) 1_555 1_555 1_555 no C3 C2 C9 118.7(2) 1_555 1_555 1_555 no O1 C3 C2 106.0(2) 1_555 1_555 1_555 no O1 C3 C4 111.2(2) 1_555 1_555 1_555 no O1 C3 C10 106.1(2) 1_555 1_555 1_555 no C2 C3 C4 113.2(2) 1_555 1_555 1_555 no C2 C3 C10 110.5(2) 1_555 1_555 1_555 no C4 C3 C10 109.5(2) 1_555 1_555 1_555 no C3 C4 C5 111.9(2) 1_555 1_555 1_555 no C3 C4 C12 116.8(2) 1_555 1_555 1_555 no C5 C4 C12 114.7(2) 1_555 1_555 1_555 no C4 C5 C6 118.8(2) 1_555 1_555 1_555 no C1 C6 C5 108.0(2) 1_555 1_555 1_555 no C1 C6 C7 110.0(2) 1_555 1_555 1_555 no C5 C6 C7 117.6(2) 1_555 1_555 1_555 no O2 C7 C6 106.5(2) 1_555 1_555 1_555 no O2 C7 C8 111.8(2) 1_555 1_555 1_555 no O2 C7 C11 105.7(2) 1_555 1_555 1_555 no C6 C7 C8 113.2(2) 1_555 1_555 1_555 no C6 C7 C11 110.4(3) 1_555 1_555 1_555 no C8 C7 C11 109.0(2) 1_555 1_555 1_555 no C7 C8 C9 111.9(2) 1_555 1_555 1_555 no C7 C8 C14 116.4(2) 1_555 1_555 1_555 no C9 C8 C14 114.5(2) 1_555 1_555 1_555 no C2 C9 C8 118.8(2) 1_555 1_555 1_555 no C4 C12 C13 123.7(3) 1_555 1_555 1_555 no C4 C12 C13' 120.2(4) 1_555 1_555 1_555 no C12 C13 C14 118.3(3) 1_555 1_555 1_555 no C12 C13 C15 108.4(3) 1_555 1_555 1_555 no C14 C13 C15 111.0(3) 1_555 1_555 1_555 no C12 C13' C14 118.9(3) 1_555 1_555 1_555 no C12 C13' C15' 108.5(7) 1_555 1_555 1_555 no C14 C13' C15' 104.2(7) 1_555 1_555 1_555 no C8 C14 C13 122.6(3) 1_555 1_555 1_555 no C8 C14 C13' 124.6(4) 1_555 1_555 1_555 no O1Et C1Et C2Et 112.1(5) 1_555 1_555 1_555 no 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 C6 C1 C2 C3 -69.2(3) 1_555 1_555 1_555 1_555 no C6 C1 C2 C9 61.2(3) 1_555 1_555 1_555 1_555 no C2 C1 C6 C5 62.0(3) 1_555 1_555 1_555 1_555 no C2 C1 C6 C7 -67.5(3) 1_555 1_555 1_555 1_555 no C1 C2 C3 O1 179.4(2) 1_555 1_555 1_555 1_555 no C1 C2 C3 C4 57.3(3) 1_555 1_555 1_555 1_555 no C1 C2 C3 C10 -66.0(3) 1_555 1_555 1_555 1_555 no C9 C2 C3 O1 55.1(3) 1_555 1_555 1_555 1_555 no C9 C2 C3 C4 -67.0(3) 1_555 1_555 1_555 1_555 no C9 C2 C3 C10 169.7(2) 1_555 1_555 1_555 1_555 no C1 C2 C9 C8 -49.1(3) 1_555 1_555 1_555 1_555 no C3 C2 C9 C8 75.9(3) 1_555 1_555 1_555 1_555 no O1 C3 C4 C5 -158.9(2) 1_555 1_555 1_555 1_555 no O1 C3 C4 C12 -23.8(3) 1_555 1_555 1_555 1_555 no C2 C3 C4 C5 -39.7(3) 1_555 1_555 1_555 1_555 no C2 C3 C4 C12 95.4(3) 1_555 1_555 1_555 1_555 no C10 C3 C4 C5 84.1(3) 1_555 1_555 1_555 1_555 no C10 C3 C4 C12 -140.8(2) 1_555 1_555 1_555 1_555 no C3 C4 C5 C6 36.3(3) 1_555 1_555 1_555 1_555 no C12 C4 C5 C6 -99.8(3) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13 -47.8(3) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13' -101.3(4) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13 86.1(3) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13' 32.6(4) 1_555 1_555 1_555 1_555 no C4 C5 C6 C1 -47.7(3) 1_555 1_555 1_555 1_555 no C4 C5 C6 C7 77.4(3) 1_555 1_555 1_555 1_555 no C1 C6 C7 O2 -179.9(2) 1_555 1_555 1_555 1_555 no C1 C6 C7 C8 56.8(3) 1_555 1_555 1_555 1_555 no C1 C6 C7 C11 -65.6(3) 1_555 1_555 1_555 1_555 no C5 C6 C7 O2 56.0(3) 1_555 1_555 1_555 1_555 no C5 C6 C7 C8 -67.3(3) 1_555 1_555 1_555 1_555 no C5 C6 C7 C11 170.2(2) 1_555 1_555 1_555 1_555 no O2 C7 C8 C9 -161.1(2) 1_555 1_555 1_555 1_555 no O2 C7 C8 C14 -26.7(3) 1_555 1_555 1_555 1_555 no C6 C7 C8 C9 -40.8(3) 1_555 1_555 1_555 1_555 no C6 C7 C8 C14 93.6(3) 1_555 1_555 1_555 1_555 no C11 C7 C8 C9 82.4(3) 1_555 1_555 1_555 1_555 no C11 C7 C8 C14 -143.1(3) 1_555 1_555 1_555 1_555 no C7 C8 C9 C2 38.7(3) 1_555 1_555 1_555 1_555 no C14 C8 C9 C2 -96.7(3) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13 -101.5(3) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13' -46.4(4) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13 31.7(4) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13' 86.9(4) 1_555 1_555 1_555 1_555 no C4 C12 C13 C14 -55.8(4) 1_555 1_555 1_555 1_555 no C4 C12 C13 C15 176.7(3) 1_555 1_555 1_555 1_555 no C4 C12 C13' C14 63.2(7) 1_555 1_555 1_555 1_555 no C4 C12 C13' C15' -178.1(7) 1_555 1_555 1_555 1_555 no C12 C13 C14 C8 63.2(5) 1_555 1_555 1_555 1_555 no C15 C13 C14 C8 -170.6(4) 1_555 1_555 1_555 1_555 no C12 C13' C14 C8 -58.1(7) 1_555 1_555 1_555 1_555 no C15' C13' C14 C8 -179.0(7) 1_555 1_555 1_555 1_555 no # Attachment 'drb278.cif' data_drb278 _database_code_depnum_ccdc_archive 'CCDC 295346' _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1996. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al,1994)' _computing_structure_refinement 'RAELS, (Rae, 1996)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C15 H26 O2, C2 H4 O2' _chemical_formula_sum 'C17 H30 O4' _chemical_formula_iupac ? _chemical_formula_weight 298.4 _chemical_absolute_configuration ? # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 7.536(3) _cell_length_b 13.657(3) _cell_length_c 17.238(7) _cell_angle_alpha 90 _cell_angle_beta 106.91(2) _cell_angle_gamma 90 _cell_volume 1697(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.17 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656.0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 1644 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_theta_max 20 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 20 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 18 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 1578 _reflns_number_gt 1055 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.065 _refine_ls_wR_factor_ref 0.081 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1055 _refine_ls_number_parameters 95 _refine_ls_goodness_of_fit_ref 1.77 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.37 _refine_diff_density_min -0.34 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1 0.5651(5) 0.2519(3) 0.3323(2) 0.0563(8) Uani O 1.0 O2 0.7267(5) 0.6265(3) 0.2310(3) 0.068(1) Uani O 1.0 C1 0.6474(9) 0.5079(5) 0.4135(4) 0.0568(8) Uani C 1.0 C2 0.6913(8) 0.4015(4) 0.3974(4) 0.0479(8) Uani C 1.0 C3 0.5145(7) 0.3512(4) 0.3450(4) 0.0462(8) Uani C 1.0 C4 0.4257(8) 0.4044(4) 0.2634(4) 0.0496(8) Uani C 1.0 C5 0.4351(8) 0.5169(4) 0.2735(4) 0.0538(9) Uani C 1.0 C6 0.6068(8) 0.5638(4) 0.3341(4) 0.0552(8) Uani C 1.0 C7 0.7808(8) 0.5728(5) 0.3064(4) 0.0555(8) Uani C 1.0 C8 0.8689(7) 0.4723(4) 0.2972(4) 0.0494(8) Uani C 1.0 C9 0.8622(7) 0.4005(4) 0.3657(4) 0.0492(8) Uani C 1.0 C10 0.3686(8) 0.3445(5) 0.3912(4) 0.055(1) Uani C 1.0 C11 0.9266(9) 0.6343(5) 0.3656(5) 0.0740(9) Uani C 1.0 C12 0.4792(8) 0.3676(5) 0.1895(4) 0.062(1) Uani C 1.0 C13 0.6697(11) 0.3516(7) 0.1857(6) 0.065(1) Uani C 0.77 C13' 0.6267(18) 0.4059(24) 0.1573(7) 0.068(1) Uani C 0.23 C14 0.8151(8) 0.4284(5) 0.2112(4) 0.058(1) Uani C 1.0 C15 0.6594(26) 0.3206(13) 0.0975(9) 0.100(2) Uani C 0.77 C15' 0.6612(71) 0.3244(35) 0.1000(25) 0.098(2) Uani C 0.23 O1Ac 0.8448(6) 0.1576(3) 0.4321(3) 0.073(2) Uani O 1.0 O2Ac 0.9801(6) 0.1513(3) 0.3351(3) 0.066(2) Uani O 1.0 C1Ac 1.1502(10) 0.1024(6) 0.4669(5) 0.096(4) Uani C 1.0 C2Ac 0.9871(9) 0.1389(5) 0.4042(5) 0.058(2) Uani C 1.0 H1O1 0.4590 0.2063 0.3093 0.067 Uani H 1.0 H1O2 0.8320 0.6354 0.2073 0.075 Uani H 1.0 H1C1 0.7562 0.5378 0.4544 0.070 Uani H 1.0 H2C1 0.5368 0.5100 0.4343 0.064 Uani H 1.0 HC2 0.7276 0.3673 0.4510 0.058 Uani H 1.0 HC4 0.2905 0.3890 0.2506 0.058 Uani H 1.0 H1C5 0.3246 0.5370 0.2907 0.062 Uani H 1.0 H2C5 0.4256 0.5454 0.2190 0.063 Uani H 1.0 HC6 0.5707 0.6317 0.3451 0.070 Uani H 1.0 HC8 0.9973 0.4795 0.2923 0.057 Uani H 1.0 H1C9 0.9726 0.4148 0.4130 0.059 Uani H 1.0 H2C9 0.8729 0.3328 0.3454 0.053 Uani H 1.0 H1C10 0.3289 0.4120 0.4015 0.059 Uani H 1.0 H2C10 0.2587 0.3069 0.3581 0.061 Uani H 1.0 H3C10 0.4232 0.3103 0.4441 0.063 Uani H 1.0 H1C11 0.9687 0.6000 0.4190 0.077 Uani H 1.0 H2C11 1.0348 0.6443 0.3439 0.079 Uani H 1.0 H3C11 0.8724 0.6993 0.3728 0.090 Uani H 1.0 H1C12 0.4233 0.4156 0.1454 0.073 Uani H 0.77 H2C12 0.4157 0.3028 0.1759 0.074 Uani H 0.77 H1'C12 0.3629 0.3730 0.1434 0.078 Uani H 0.23 H2'C12 0.5108 0.2969 0.2012 0.067 Uani H 0.23 HC13 0.7177 0.2933 0.2206 0.066 Uani H 0.77 HC13' 0.5782 0.4653 0.1240 0.077 Uani H 0.23 H1C14 0.7733 0.4845 0.1729 0.065 Uani H 0.77 H2C14 0.9311 0.3997 0.2036 0.068 Uani H 0.77 H1'C14 0.8689 0.4746 0.1791 0.068 Uani H 0.23 H2'C14 0.8828 0.3646 0.2174 0.064 Uani H 0.23 H1C15 0.7876 0.3094 0.0936 0.109 Uani H 0.77 H2C15 0.5856 0.2590 0.0833 0.116 Uani H 0.77 H3C15 0.5984 0.3738 0.0590 0.109 Uani H 0.77 H1C15' 0.7606 0.3462 0.0760 0.109 Uani H 0.23 H2C15' 0.7009 0.2628 0.1316 0.098 Uani H 0.23 H3C15' 0.5442 0.3121 0.0555 0.119 Uani H 0.23 H1O1Ac 0.7387 0.1934 0.3942 0.066 Uani H 1.0 H1C1Ac 1.2530 0.0896 0.4424 0.118 Uani H 1.0 H2C1Ac 1.1912 0.1524 0.5109 0.139 Uani H 1.0 H3C1Ac 1.1176 0.0402 0.4902 0.104 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1 0.048(1) 0.046(1) 0.078(1) 0.0002(9) 0.0227(9) -0.0009(8) O O2 0.051(2) 0.060(1) 0.097(2) 0.006(1) 0.029(2) 0.023(1) O C1 0.056(1) 0.059(1) 0.058(1) -0.004(1) 0.021(1) -0.015(1) C C2 0.041(1) 0.055(1) 0.047(1) 0.0004(8) 0.0116(9) -0.0009(9) C C3 0.038(1) 0.047(1) 0.053(1) 0.0013(8) 0.0140(8) -0.0001(8) C C4 0.038(1) 0.056(1) 0.052(1) -0.0010(9) 0.009(1) -0.0001(9) C C5 0.041(1) 0.054(1) 0.068(2) 0.007(1) 0.017(1) 0.009(1) C C6 0.049(1) 0.045(1) 0.075(2) 0.0016(9) 0.024(1) -0.0048(9) C C7 0.046(1) 0.047(1) 0.075(1) -0.0009(9) 0.0204(9) 0.0008(9) C C8 0.039(1) 0.051(1) 0.059(1) 0.0017(8) 0.0161(9) 0.0025(9) C C9 0.037(1) 0.054(1) 0.055(1) 0.0018(9) 0.011(1) 0.0030(9) C C10 0.044(1) 0.059(2) 0.066(2) 0.004(1) 0.022(1) 0.008(1) C C11 0.061(2) 0.057(1) 0.104(3) -0.015(2) 0.025(2) -0.014(2) C C12 0.055(1) 0.079(2) 0.050(1) -0.009(1) 0.011(1) -0.011(1) C C13 0.066(2) 0.077(2) 0.057(1) -0.005(1) 0.026(1) -0.016(1) C C13' 0.065(2) 0.092(2) 0.049(1) -0.005(2) 0.020(1) -0.007(1) C C14 0.054(2) 0.068(2) 0.058(1) 0.003(1) 0.026(1) 0.000(1) C C15 0.111(4) 0.132(4) 0.068(2) -0.018(4) 0.043(2) -0.037(2) C C15' 0.109(4) 0.130(4) 0.067(2) -0.017(3) 0.042(2) -0.035(2) C O1Ac 0.071(3) 0.085(3) 0.070(3) 0.017(2) 0.031(2) 0.013(2) O O2Ac 0.062(3) 0.074(3) 0.066(3) 0.014(2) 0.024(2) -0.005(3) O C1Ac 0.069(3) 0.105(5) 0.094(4) 0.021(4) -0.008(3) 0.010(4) C C2Ac 0.043(2) 0.068(2) 0.059(3) -0.001(2) 0.006(2) -0.007(2) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.443(6) 1_555 1_555 no O2 C7 1.444(7) 1_555 1_555 no C1 C2 1.533(8) 1_555 1_555 no C1 C6 1.518(8) 1_555 1_555 no C2 C3 1.537(7) 1_555 1_555 no C2 C9 1.538(8) 1_555 1_555 no C3 C4 1.551(8) 1_555 1_555 no C3 C10 1.537(8) 1_555 1_555 no C4 C5 1.546(8) 1_555 1_555 no C4 C12 1.529(8) 1_555 1_555 no C5 C6 1.546(8) 1_555 1_555 no C6 C7 1.526(8) 1_555 1_555 no C7 C8 1.553(8) 1_555 1_555 no C7 C11 1.518(8) 1_555 1_555 no C8 C9 1.547(8) 1_555 1_555 no C8 C14 1.540(8) 1_555 1_555 no C12 C13 1.473(9) 1_555 1_555 no C12 C13' 1.476(10) 1_555 1_555 no C13 C14 1.488(9) 1_555 1_555 no C13 C15 1.558(12) 1_555 1_555 no C13' C14 1.485(10) 1_555 1_555 no C13' C15' 1.559(15) 1_555 1_555 no O1Ac C2Ac 1.322(7) 1_555 1_555 no O2Ac C2Ac 1.189(7) 1_555 1_555 no C1Ac C2Ac 1.468(9) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 108.2(5) 1_555 1_555 1_555 no C1 C2 C3 109.5(5) 1_555 1_555 1_555 no C1 C2 C9 108.6(5) 1_555 1_555 1_555 no C3 C2 C9 117.3(5) 1_555 1_555 1_555 no O1 C3 C2 106.7(4) 1_555 1_555 1_555 no O1 C3 C4 111.6(5) 1_555 1_555 1_555 no O1 C3 C10 106.4(5) 1_555 1_555 1_555 no C2 C3 C4 113.3(5) 1_555 1_555 1_555 no C2 C3 C10 110.5(5) 1_555 1_555 1_555 no C4 C3 C10 108.2(4) 1_555 1_555 1_555 no C3 C4 C5 111.7(5) 1_555 1_555 1_555 no C3 C4 C12 116.8(5) 1_555 1_555 1_555 no C5 C4 C12 114.0(5) 1_555 1_555 1_555 no C4 C5 C6 119.3(5) 1_555 1_555 1_555 no C1 C6 C5 108.1(5) 1_555 1_555 1_555 no C1 C6 C7 110.9(5) 1_555 1_555 1_555 no C5 C6 C7 116.6(5) 1_555 1_555 1_555 no O2 C7 C6 106.2(5) 1_555 1_555 1_555 no O2 C7 C8 112.0(5) 1_555 1_555 1_555 no O2 C7 C11 106.4(5) 1_555 1_555 1_555 no C6 C7 C8 113.2(5) 1_555 1_555 1_555 no C6 C7 C11 110.7(6) 1_555 1_555 1_555 no C8 C7 C11 108.1(5) 1_555 1_555 1_555 no C7 C8 C9 111.8(5) 1_555 1_555 1_555 no C7 C8 C14 116.2(5) 1_555 1_555 1_555 no C9 C8 C14 115.5(5) 1_555 1_555 1_555 no C2 C9 C8 118.8(5) 1_555 1_555 1_555 no C4 C12 C13 125.7(6) 1_555 1_555 1_555 no C4 C12 C13' 127.4(11) 1_555 1_555 1_555 no C12 C13 C14 121.7(6) 1_555 1_555 1_555 no C12 C13 C15 108.1(9) 1_555 1_555 1_555 no C14 C13 C15 107.6(9) 1_555 1_555 1_555 no C12 C13' C14 121.7(8) 1_555 1_555 1_555 no C12 C13' C15' 105.6(25) 1_555 1_555 1_555 no C14 C13' C15' 103.8(24) 1_555 1_555 1_555 no C8 C14 C13 121.6(6) 1_555 1_555 1_555 no C8 C14 C13' 128.2(10) 1_555 1_555 1_555 no O1Ac C2Ac O2Ac 122.2(6) 1_555 1_555 1_555 no O1Ac C2Ac C1Ac 113.1(7) 1_555 1_555 1_555 no O2Ac C2Ac C1Ac 124.8(7) 1_555 1_555 1_555 no 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 C6 C1 C2 C3 -68.9(6) 1_555 1_555 1_555 1_555 no C6 C1 C2 C9 60.4(6) 1_555 1_555 1_555 1_555 no C2 C1 C6 C5 61.6(6) 1_555 1_555 1_555 1_555 no C2 C1 C6 C7 -67.3(6) 1_555 1_555 1_555 1_555 no C1 C2 C3 O1 -179.9(5) 1_555 1_555 1_555 1_555 no C1 C2 C3 C4 57.0(6) 1_555 1_555 1_555 1_555 no C1 C2 C3 C10 -64.6(6) 1_555 1_555 1_555 1_555 no C9 C2 C3 O1 55.7(6) 1_555 1_555 1_555 1_555 no C9 C2 C3 C4 -67.4(7) 1_555 1_555 1_555 1_555 no C9 C2 C3 C10 171.0(5) 1_555 1_555 1_555 1_555 no C1 C2 C9 C8 -47.6(7) 1_555 1_555 1_555 1_555 no C3 C2 C9 C8 77.2(7) 1_555 1_555 1_555 1_555 no O1 C3 C4 C5 -159.7(4) 1_555 1_555 1_555 1_555 no O1 C3 C4 C12 -25.9(7) 1_555 1_555 1_555 1_555 no C2 C3 C4 C5 -39.3(7) 1_555 1_555 1_555 1_555 no C2 C3 C4 C12 94.6(6) 1_555 1_555 1_555 1_555 no C10 C3 C4 C5 83.6(6) 1_555 1_555 1_555 1_555 no C10 C3 C4 C12 -142.6(5) 1_555 1_555 1_555 1_555 no C3 C4 C5 C6 35.9(7) 1_555 1_555 1_555 1_555 no C12 C4 C5 C6 -99.3(6) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13 -50.4(9) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13' -94.8(14) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13 82.4(8) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13' 38.0(14) 1_555 1_555 1_555 1_555 no C4 C5 C6 C1 -47.5(7) 1_555 1_555 1_555 1_555 no C4 C5 C6 C7 78.2(7) 1_555 1_555 1_555 1_555 no C1 C6 C7 O2 179.9(5) 1_555 1_555 1_555 1_555 no C1 C6 C7 C8 56.5(7) 1_555 1_555 1_555 1_555 no C1 C6 C7 C11 -65.0(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 O2 55.6(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 C8 -67.7(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 C11 170.8(5) 1_555 1_555 1_555 1_555 no O2 C7 C8 C9 -159.5(4) 1_555 1_555 1_555 1_555 no O2 C7 C8 C14 -24.0(7) 1_555 1_555 1_555 1_555 no C6 C7 C8 C9 -39.5(7) 1_555 1_555 1_555 1_555 no C6 C7 C8 C14 96.1(6) 1_555 1_555 1_555 1_555 no C11 C7 C8 C9 83.5(6) 1_555 1_555 1_555 1_555 no C11 C7 C8 C14 -140.9(6) 1_555 1_555 1_555 1_555 no C7 C8 C9 C2 36.9(7) 1_555 1_555 1_555 1_555 no C14 C8 C9 C2 -99.0(6) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13 -99.2(7) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13' -56.8(16) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13 34.7(8) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13' 77.1(15) 1_555 1_555 1_555 1_555 no C4 C12 C13 C14 -51.1(12) 1_555 1_555 1_555 1_555 no C4 C12 C13 C15 -176.2(9) 1_555 1_555 1_555 1_555 no C4 C12 C13' C14 45.6(32) 1_555 1_555 1_555 1_555 no C4 C12 C13' C15' 163.3(21) 1_555 1_555 1_555 1_555 no C12 C13 C14 C8 57.6(11) 1_555 1_555 1_555 1_555 no C15 C13 C14 C8 -177.0(9) 1_555 1_555 1_555 1_555 no C12 C13' C14 C8 -37.0(33) 1_555 1_555 1_555 1_555 no C15' C13' C14 C8 -155.5(21) 1_555 1_555 1_555 1_555 no # Attachment 'drb279.cif' data_drb279 _database_code_depnum_ccdc_archive 'CCDC 295347' _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1996. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al,1994)' _computing_structure_refinement 'RAELS, (Rae, 1996)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C15 H26 O2, C3 H8 O' _chemical_formula_sum 'C18 H34 O3' _chemical_formula_iupac ? _chemical_formula_weight 298.5 _chemical_absolute_configuration ? # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 6.908(4) _cell_length_b 13.833(5) _cell_length_c 18.981(7) _cell_angle_alpha 90 _cell_angle_beta 97.99(2) _cell_angle_gamma 90 _cell_volume 1796(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.10 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664.0 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 2584 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_theta_max 23 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 23 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 2497 _reflns_number_gt 1191 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.068 _refine_ls_wR_factor_ref 0.092 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1191 _refine_ls_number_parameters 98 _refine_ls_goodness_of_fit_ref 1.85 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.52 _refine_diff_density_min -0.58 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1 0.7653(6) 0.2252(3) 0.2028(3) 0.052(2) Uani O 1.0 O2 0.9123(6) 0.6010(3) 0.3158(2) 0.0470(9) Uani O 1.0 C1 0.8870(10) 0.3450(5) 0.3798(4) 0.048(1) Uani C 1.0 C2 0.9179(9) 0.2919(5) 0.3123(4) 0.044(1) Uani C 1.0 C3 0.7229(9) 0.2752(5) 0.2655(4) 0.043(1) Uani C 1.0 C4 0.6102(9) 0.3718(5) 0.2458(4) 0.0419(9) Uani C 1.0 C5 0.6261(9) 0.4425(5) 0.3094(4) 0.042(1) Uani C 1.0 C6 0.8208(9) 0.4481(5) 0.3595(4) 0.042(1) Uani C 1.0 C7 0.9888(9) 0.5040(5) 0.3337(4) 0.0415(9) Uani C 1.0 C8 1.0673(9) 0.4570(5) 0.2712(4) 0.044(1) Uani C 1.0 C9 1.0792(9) 0.3444(5) 0.2787(4) 0.047(1) Uani C 1.0 C10 0.5939(10) 0.2087(5) 0.3036(4) 0.052(1) Uani C 1.0 C11 1.1554(9) 0.5178(5) 0.3961(4) 0.054(2) Uani C 1.0 C12 0.6364(10) 0.4175(5) 0.1744(4) 0.052(1) Uani C 1.0 C13 0.8265(16) 0.4385(10) 0.1485(6) 0.059(2) Uani C 0.51 C13' 0.7686(15) 0.5029(8) 0.1739(8) 0.056(1) Uani C 0.49 C14 0.9821(10) 0.4912(5) 0.1963(4) 0.053(1) Uani C 1.0 C15 0.7896(31) 0.4858(15) 0.0727(8) 0.090(4) Uani C 0.51 C15' 0.7480(32) 0.5402(14) 0.0957(9) 0.085(3) Uani C 0.49 O1Ip 0.3924(6) 0.1827(3) 0.1229(3) 0.060(7) Uani O 1.0 C1Ip 0.3067(8) 0.2022(5) 0.0511(4) 0.061(6) Uani C 1.0 C2Ip 0.1619(12) 0.2820(6) 0.0507(4) 0.083(9) Uani C 1.0 C3Ip 0.4644(13) 0.2217(7) 0.0069(4) 0.097(9) Uani C 1.0 H1O1 0.6350 0.2104 0.1749 0.057 Uani H 1.0 H1O2 1.0245 0.6443 0.3093 0.053 Uani H 1.0 H1C1 1.0121 0.3467 0.4133 0.058 Uani H 1.0 H2C1 0.7843 0.3114 0.4030 0.056 Uani H 1.0 HC2 0.9707 0.2266 0.3272 0.054 Uani H 1.0 HC4 0.4698 0.3518 0.2391 0.049 Uani H 1.0 H1C5 0.5231 0.4238 0.3390 0.050 Uani H 1.0 H2C5 0.5978 0.5088 0.2895 0.047 Uani H 1.0 HC6 0.7927 0.4804 0.4041 0.051 Uani H 1.0 HC8 1.1931 0.4864 0.2614 0.053 Uani H 1.0 H1C9 1.2065 0.3289 0.3084 0.057 Uani H 1.0 H2C9 1.0784 0.3173 0.2299 0.053 Uani H 1.0 H1C10 0.5617 0.2414 0.3476 0.056 Uani H 1.0 H2C10 0.4703 0.1943 0.2713 0.056 Uani H 1.0 H3C10 0.6652 0.1471 0.3170 0.060 Uani H 1.0 H1C11 1.2138 0.4535 0.4109 0.060 Uani H 1.0 H2C11 1.2583 0.5607 0.3808 0.059 Uani H 1.0 H3C11 1.1019 0.5481 0.4372 0.061 Uani H 1.0 H1C12 0.5677 0.4812 0.1736 0.058 Uani H 0.51 H2C12 0.5647 0.3739 0.1376 0.062 Uani H 0.51 H1'C12 0.5040 0.4381 0.1511 0.064 Uani H 0.49 H2'C12 0.6881 0.3660 0.1451 0.057 Uani H 0.49 HC13 0.8841 0.3737 0.1409 0.061 Uani H 0.51 HC13' 0.7204 0.5547 0.2039 0.054 Uani H 0.49 H1C14 0.9283 0.5572 0.2026 0.055 Uani H 0.51 H2C14 1.0959 0.4960 0.1691 0.066 Uani H 0.51 H1'C14 1.0420 0.5558 0.1897 0.061 Uani H 0.49 H2'C14 1.0279 0.4437 0.1624 0.062 Uani H 0.49 H1C15 0.9177 0.4995 0.0559 0.103 Uani H 0.51 H2C15 0.7120 0.4404 0.0388 0.102 Uani H 0.51 H3C15 0.7154 0.5475 0.0751 0.095 Uani H 0.51 H1C15' 0.8347 0.5977 0.0931 0.094 Uani H 0.49 H2C15' 0.7871 0.4879 0.0642 0.094 Uani H 0.49 H3C15' 0.6092 0.5590 0.0796 0.097 Uani H 0.49 H1O1Ip 0.2829 0.1534 0.1449 0.062 Uani H 1.0 HC1Ip 0.2350 0.1428 0.0320 0.075 Uani H 1.0 H1C2Ip 0.0609 0.2639 0.0814 0.112 Uani H 1.0 H2C2Ip 0.2302 0.3423 0.0696 0.100 Uani H 1.0 H3C2Ip 0.0972 0.2935 0.0009 0.097 Uani H 1.0 H1C3Ip 0.5556 0.1652 0.0097 0.131 Uani H 1.0 H2C3Ip 0.4053 0.2320 -0.0437 0.110 Uani H 1.0 H3C3Ip 0.5383 0.2809 0.0250 0.117 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1 0.044(2) 0.040(1) 0.073(2) -0.004(1) 0.013(2) -0.014(2) O O2 0.038(2) 0.032(1) 0.072(2) -0.002(1) 0.009(1) -0.003(1) O C1 0.048(2) 0.041(1) 0.054(2) -0.003(1) 0.003(1) 0.007(1) C C2 0.036(1) 0.032(1) 0.065(2) 0.002(1) 0.005(1) 0.003(1) C C3 0.035(1) 0.032(1) 0.062(2) -0.0010(9) 0.0086(8) -0.002(1) C C4 0.033(1) 0.035(1) 0.058(2) -0.0003(9) 0.004(1) -0.0009(9) C C5 0.032(1) 0.034(1) 0.062(2) 0.000(1) 0.011(1) -0.003(1) C C6 0.038(1) 0.037(1) 0.051(2) -0.0022(9) 0.009(1) -0.002(1) C C7 0.033(1) 0.034(1) 0.058(2) -0.0012(9) 0.0066(9) -0.002(1) C C8 0.034(1) 0.036(1) 0.064(2) -0.002(1) 0.013(1) -0.002(1) C C9 0.032(1) 0.036(1) 0.074(3) 0.001(1) 0.011(1) -0.005(1) C C10 0.044(2) 0.035(1) 0.079(3) -0.006(2) 0.014(2) 0.002(1) C C11 0.043(2) 0.046(2) 0.070(2) -0.004(2) -0.003(2) -0.007(2) C C12 0.052(2) 0.047(2) 0.055(2) -0.003(1) -0.002(1) 0.003(1) C C13 0.069(3) 0.057(2) 0.051(2) -0.011(2) 0.012(1) 0.003(1) C C13' 0.061(2) 0.048(2) 0.056(2) -0.006(2) 0.003(2) 0.011(2) C C14 0.055(2) 0.047(2) 0.059(2) -0.009(2) 0.019(1) 0.003(1) C C15 0.124(7) 0.092(5) 0.053(2) -0.025(5) 0.009(2) 0.014(2) C C15' 0.113(6) 0.079(4) 0.061(2) -0.018(4) -0.001(3) 0.024(3) C O1Ip 0.054(9) 0.060(6) 0.063(5) -0.011(3) 0.001(4) 0.004(4) O C1Ip 0.063(9) 0.058(5) 0.061(4) -0.010(4) 0.002(5) 0.003(3) C C2Ip 0.090(9) 0.075(9) 0.081(9) 0.014(6) -0.001(8) 0.011(8) C C3Ip 0.100(9) 0.110(8) 0.086(5) -0.004(6) 0.033(6) 0.025(6) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.443(7) 1_555 1_555 no O2 C7 1.466(8) 1_555 1_555 no C1 C2 1.516(9) 1_555 1_555 no C1 C6 1.531(9) 1_555 1_555 no C2 C3 1.524(9) 1_555 1_555 no C2 C9 1.540(9) 1_555 1_555 no C3 C4 1.566(9) 1_555 1_555 no C3 C10 1.531(9) 1_555 1_555 no C4 C5 1.546(9) 1_555 1_555 no C4 C12 1.528(9) 1_555 1_555 no C5 C6 1.537(9) 1_555 1_555 no C6 C7 1.530(8) 1_555 1_555 no C7 C8 1.516(9) 1_555 1_555 no C7 C11 1.545(9) 1_555 1_555 no C8 C9 1.565(9) 1_555 1_555 no C8 C14 1.537(9) 1_555 1_555 no C12 C13 1.493(11) 1_555 1_555 no C12 C13' 1.494(11) 1_555 1_555 no C13 C14 1.495(11) 1_555 1_555 no C13 C15 1.568(14) 1_555 1_555 no C13' C14 1.486(11) 1_555 1_555 no C13' C15' 1.560(14) 1_555 1_555 no O1Ip C1Ip 1.434(8) 1_555 1_555 no C1Ip C2Ip 1.489(7) 1_555 1_555 no C1Ip C3Ip 1.489(7) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 108.1(6) 1_555 1_555 1_555 no C1 C2 C3 110.4(5) 1_555 1_555 1_555 no C1 C2 C9 108.4(6) 1_555 1_555 1_555 no C3 C2 C9 117.5(6) 1_555 1_555 1_555 no O1 C3 C2 106.8(5) 1_555 1_555 1_555 no O1 C3 C4 111.3(5) 1_555 1_555 1_555 no O1 C3 C10 107.5(5) 1_555 1_555 1_555 no C2 C3 C4 112.3(5) 1_555 1_555 1_555 no C2 C3 C10 109.9(6) 1_555 1_555 1_555 no C4 C3 C10 108.9(5) 1_555 1_555 1_555 no C3 C4 C5 111.9(6) 1_555 1_555 1_555 no C3 C4 C12 116.7(6) 1_555 1_555 1_555 no C5 C4 C12 115.3(6) 1_555 1_555 1_555 no C4 C5 C6 118.4(5) 1_555 1_555 1_555 no C1 C6 C5 108.3(5) 1_555 1_555 1_555 no C1 C6 C7 109.7(5) 1_555 1_555 1_555 no C5 C6 C7 117.7(5) 1_555 1_555 1_555 no O2 C7 C6 105.8(5) 1_555 1_555 1_555 no O2 C7 C8 111.6(5) 1_555 1_555 1_555 no O2 C7 C11 105.7(5) 1_555 1_555 1_555 no C6 C7 C8 113.8(5) 1_555 1_555 1_555 no C6 C7 C11 109.5(6) 1_555 1_555 1_555 no C8 C7 C11 110.1(5) 1_555 1_555 1_555 no C7 C8 C9 112.1(6) 1_555 1_555 1_555 no C7 C8 C14 117.3(6) 1_555 1_555 1_555 no C9 C8 C14 113.5(6) 1_555 1_555 1_555 no C2 C9 C8 118.3(6) 1_555 1_555 1_555 no C4 C12 C13 126.1(7) 1_555 1_555 1_555 no C4 C12 C13' 118.6(7) 1_555 1_555 1_555 no C12 C13 C14 119.1(7) 1_555 1_555 1_555 no C12 C13 C15 110.1(11) 1_555 1_555 1_555 no C14 C13 C15 111.4(11) 1_555 1_555 1_555 no C12 C13' C14 119.7(7) 1_555 1_555 1_555 no C12 C13' C15' 107.0(11) 1_555 1_555 1_555 no C14 C13' C15' 105.3(11) 1_555 1_555 1_555 no C8 C14 C13 124.2(7) 1_555 1_555 1_555 no C8 C14 C13' 122.3(7) 1_555 1_555 1_555 no O1Ip C1Ip C2Ip 109.4(4) 1_555 1_555 1_555 no O1Ip C1Ip C3Ip 109.4(4) 1_555 1_555 1_555 no C2Ip C1Ip C3Ip 114.0(7) 1_555 1_555 1_555 no 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 C6 C1 C2 C3 -68.8(7) 1_555 1_555 1_555 1_555 no C6 C1 C2 C9 61.2(6) 1_555 1_555 1_555 1_555 no C2 C1 C6 C5 61.6(7) 1_555 1_555 1_555 1_555 no C2 C1 C6 C7 -68.2(6) 1_555 1_555 1_555 1_555 no C1 C2 C3 O1 179.7(5) 1_555 1_555 1_555 1_555 no C1 C2 C3 C4 57.4(7) 1_555 1_555 1_555 1_555 no C1 C2 C3 C10 -64.0(7) 1_555 1_555 1_555 1_555 no C9 C2 C3 O1 54.7(7) 1_555 1_555 1_555 1_555 no C9 C2 C3 C4 -67.6(7) 1_555 1_555 1_555 1_555 no C9 C2 C3 C10 171.0(5) 1_555 1_555 1_555 1_555 no C1 C2 C9 C8 -47.2(8) 1_555 1_555 1_555 1_555 no C3 C2 C9 C8 78.7(8) 1_555 1_555 1_555 1_555 no O1 C3 C4 C5 -160.1(5) 1_555 1_555 1_555 1_555 no O1 C3 C4 C12 -24.2(7) 1_555 1_555 1_555 1_555 no C2 C3 C4 C5 -40.4(7) 1_555 1_555 1_555 1_555 no C2 C3 C4 C12 95.5(7) 1_555 1_555 1_555 1_555 no C10 C3 C4 C5 81.7(6) 1_555 1_555 1_555 1_555 no C10 C3 C4 C12 -142.5(6) 1_555 1_555 1_555 1_555 no C3 C4 C5 C6 37.6(8) 1_555 1_555 1_555 1_555 no C12 C4 C5 C6 -98.9(7) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13 -51.4(10) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13' -103.1(8) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13 83.0(9) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13' 31.3(9) 1_555 1_555 1_555 1_555 no C4 C5 C6 C1 -48.3(8) 1_555 1_555 1_555 1_555 no C4 C5 C6 C7 76.9(8) 1_555 1_555 1_555 1_555 no C1 C6 C7 O2 -179.9(5) 1_555 1_555 1_555 1_555 no C1 C6 C7 C8 57.3(7) 1_555 1_555 1_555 1_555 no C1 C6 C7 C11 -66.4(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 O2 55.7(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 C8 -67.1(7) 1_555 1_555 1_555 1_555 no C5 C6 C7 C11 169.2(6) 1_555 1_555 1_555 1_555 no O2 C7 C8 C9 -159.5(5) 1_555 1_555 1_555 1_555 no O2 C7 C8 C14 -25.6(7) 1_555 1_555 1_555 1_555 no C6 C7 C8 C9 -39.9(7) 1_555 1_555 1_555 1_555 no C6 C7 C8 C14 94.0(7) 1_555 1_555 1_555 1_555 no C11 C7 C8 C9 83.4(7) 1_555 1_555 1_555 1_555 no C11 C7 C8 C14 -142.6(6) 1_555 1_555 1_555 1_555 no C7 C8 C9 C2 36.3(8) 1_555 1_555 1_555 1_555 no C14 C8 C9 C2 -99.5(7) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13 -99.4(9) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13' -46.3(10) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13 33.9(10) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13' 87.0(9) 1_555 1_555 1_555 1_555 no C4 C12 C13 C14 -49.3(14) 1_555 1_555 1_555 1_555 no C4 C12 C13 C15 -179.8(10) 1_555 1_555 1_555 1_555 no C4 C12 C13' C14 66.8(13) 1_555 1_555 1_555 1_555 no C4 C12 C13' C15' -173.8(10) 1_555 1_555 1_555 1_555 no C12 C13 C14 C8 56.7(14) 1_555 1_555 1_555 1_555 no C15 C13 C14 C8 -173.4(11) 1_555 1_555 1_555 1_555 no C12 C13' C14 C8 -60.8(13) 1_555 1_555 1_555 1_555 no C15' C13' C14 C8 178.9(10) 1_555 1_555 1_555 1_555 no # Attachment 'drb282.cif' data_drb282 _database_code_depnum_ccdc_archive 'CCDC 295348' _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1996. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al,1994)' _computing_structure_refinement 'RAELS, (Rae, 1996)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety '2(C15 H26 O2), 1.5(C2 H6 O2)' _chemical_formula_sum 'C33 H61 O7' _chemical_formula_iupac ? _chemical_formula_weight 569.8 _chemical_absolute_configuration ? # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.777(4) _cell_length_b 14.093(7) _cell_length_c 15.210(7) _cell_angle_alpha 86.12(3) _cell_angle_beta 82.12(2) _cell_angle_gamma 79.66(2) _cell_volume 1623(1) _cell_formula_units_Z 2 _cell_measurement_reflns_used 11 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.17 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 630.0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 4713 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_theta_max 23 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 23 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 0 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 4510 _reflns_number_gt 2493 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.076 _refine_ls_wR_factor_ref 0.092 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2493 _refine_ls_number_parameters 187 _refine_ls_goodness_of_fit_ref 1.89 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.79 _refine_diff_density_min -0.61 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1A 0.6837(5) 0.3887(3) 0.1315(3) 0.0570(8) Uani O 1.0 O2A 0.9717(5) 0.0406(3) 0.2979(3) 0.0604(8) Uani O 1.0 C1A 0.7210(8) 0.1241(4) 0.1062(4) 0.0585(7) Uani C 1.0 C2A 0.7631(7) 0.2248(4) 0.0919(4) 0.0509(8) Uani C 1.0 C3A 0.6304(7) 0.2948(4) 0.1488(4) 0.0478(8) Uani C 1.0 C4A 0.6174(7) 0.2657(4) 0.2490(4) 0.0497(8) Uani C 1.0 C5A 0.6299(7) 0.1554(4) 0.2655(4) 0.0539(8) Uani C 1.0 C6A 0.7553(8) 0.0877(4) 0.2005(4) 0.0544(7) Uani C 1.0 C7A 0.9537(7) 0.0741(4) 0.2073(4) 0.0534(7) Uani C 1.0 C8A 1.0327(7) 0.1655(4) 0.1822(4) 0.0511(8) Uani C 1.0 C9A 0.9578(7) 0.2208(4) 0.1005(4) 0.0544(9) Uani C 1.0 C10A 0.4495(8) 0.3052(4) 0.1182(4) 0.058(1) Uani C 1.0 C11A 1.0535(9) -0.0077(5) 0.1484(5) 0.073(1) Uani C 1.0 C12A 0.7295(8) 0.3125(4) 0.3039(4) 0.0591(9) Uani C 1.0 C13A 0.9012(8) 0.2627(4) 0.3273(4) 0.061(1) Uani C 1.0 C14A 1.0488(8) 0.2282(4) 0.2587(4) 0.057(1) Uani C 1.0 C15A 0.9671(10) 0.3240(5) 0.3917(5) 0.091(2) Uani C 1.0 O1B 0.4182(5) 0.5499(3) 0.1577(3) 0.0583(9) Uani O 1.0 O2B 0.5375(5) 0.8461(3) 0.3652(3) 0.0633(8) Uani O 1.0 C1B 0.3791(9) 0.6098(5) 0.3955(4) 0.0710(7) Uani C 1.0 C2B 0.4600(8) 0.5660(4) 0.3060(4) 0.0589(8) Uani C 1.0 C3B 0.3318(7) 0.5961(4) 0.2392(4) 0.0539(9) Uani C 1.0 C4B 0.2829(7) 0.7054(4) 0.2240(4) 0.0532(9) Uani C 1.0 C5B 0.2491(8) 0.7566(4) 0.3139(4) 0.0589(9) Uani C 1.0 C6B 0.3712(8) 0.7186(4) 0.3841(4) 0.0623(7) Uani C 1.0 C7B 0.5557(8) 0.7422(4) 0.3735(4) 0.0610(7) Uani C 1.0 C8B 0.6754(7) 0.6948(4) 0.2933(4) 0.0593(8) Uani C 1.0 C9B 0.6447(8) 0.5917(4) 0.2830(4) 0.0614(9) Uani C 1.0 C10B 0.1641(8) 0.5525(5) 0.2649(5) 0.071(2) Uani C 1.0 C11B 0.6440(10) 0.7104(5) 0.4579(5) 0.0865(9) Uani C 1.0 C12B 0.3996(8) 0.7520(4) 0.1484(4) 0.057(1) Uani C 1.0 C13B 0.5309(8) 0.8132(4) 0.1691(4) 0.061(1) Uani C 1.0 C14B 0.6912(8) 0.7588(4) 0.2072(4) 0.062(1) Uani C 1.0 C15B 0.5905(10) 0.8689(5) 0.0843(5) 0.088(2) Uani C 1.0 O1G1 0.1789(6) 0.5550(3) 0.0343(3) 0.077(1) Uani O 1.0 C1G1 0.0733(11) 0.4897(8) 0.0235(6) 0.219(4) Uani C 1.0 O1G2 0.2928(6) 1.0053(3) 0.3535(3) 0.080(2) Uani O 1.0 O2G2 0.2074(6) 1.0666(4) 0.5860(3) 0.091(2) Uani O 1.0 C1G2 0.2786(11) 1.0591(6) 0.4298(6) 0.100(3) Uani C 1.0 C2G2 0.2399(10) 1.0014(6) 0.5078(6) 0.094(3) Uani C 1.0 H1O1A 0.5886 0.4464 0.1409 0.066 Uani H 1.0 H1O2A 1.0908 0.0275 0.3185 0.066 Uani H 1.0 H1C1A 0.7980 0.0807 0.0619 0.071 Uani H 1.0 H2C1A 0.5945 0.1252 0.0993 0.066 Uani H 1.0 H1C2A 0.7481 0.2451 0.0287 0.062 Uani H 1.0 H1C4A 0.4931 0.2927 0.2727 0.059 Uani H 1.0 H1C5A 0.5089 0.1407 0.2654 0.064 Uani H 1.0 H2C5A 0.6676 0.1390 0.3258 0.060 Uani H 1.0 H1C6A 0.7202 0.0225 0.2105 0.068 Uani H 1.0 H1C8A 1.1580 0.1401 0.1590 0.061 Uani H 1.0 H1C9A 1.0273 0.1901 0.0463 0.067 Uani H 1.0 H2C9A 0.9774 0.2889 0.1013 0.059 Uani H 1.0 H1C10A 0.4061 0.2422 0.1287 0.063 Uani H 1.0 H2C10A 0.3656 0.3560 0.1525 0.063 Uani H 1.0 H3C10A 0.4580 0.3242 0.0534 0.064 Uani H 1.0 H1C11A 1.0449 0.0121 0.0846 0.079 Uani H 1.0 H2C11A 1.1802 -0.0212 0.1585 0.078 Uani H 1.0 H3C11A 1.0005 -0.0672 0.1639 0.085 Uani H 1.0 H1C12A 0.6542 0.3288 0.3614 0.074 Uani H 1.0 H2C12A 0.7520 0.3734 0.2701 0.064 Uani H 1.0 H1C13A 0.8760 0.2035 0.3631 0.063 Uani H 1.0 H1C14A 1.1432 0.1902 0.2916 0.064 Uani H 1.0 H2C14A 1.0896 0.2875 0.2298 0.065 Uani H 1.0 H1C15A 1.0839 0.2904 0.4078 0.098 Uani H 1.0 H2C15A 0.9798 0.3885 0.3625 0.100 Uani H 1.0 H3C15A 0.8803 0.3328 0.4467 0.106 Uani H 1.0 H1O1B 0.3330 0.5517 0.1138 0.065 Uani H 1.0 H1O2B 0.6313 0.8782 0.3831 0.073 Uani H 1.0 H1C1B 0.4543 0.5829 0.4427 0.086 Uani H 1.0 H2C1B 0.2578 0.5948 0.4124 0.083 Uani H 1.0 H1C2B 0.4744 0.4942 0.3150 0.070 Uani H 1.0 H1C4B 0.1644 0.7151 0.2030 0.064 Uani H 1.0 H1C5B 0.1262 0.7518 0.3410 0.074 Uani H 1.0 H2C5B 0.2587 0.8260 0.3000 0.061 Uani H 1.0 H1C6B 0.3104 0.7460 0.4414 0.078 Uani H 1.0 H1C8B 0.7961 0.6850 0.3119 0.074 Uani H 1.0 H1C9B 0.7226 0.5481 0.3214 0.077 Uani H 1.0 H2C9B 0.6837 0.5767 0.2192 0.064 Uani H 1.0 H1C10B 0.0981 0.5812 0.3206 0.082 Uani H 1.0 H2C10B 0.0883 0.5667 0.2159 0.077 Uani H 1.0 H3C10B 0.1966 0.4810 0.2748 0.079 Uani H 1.0 H1C11B 0.6595 0.6385 0.4665 0.095 Uani H 1.0 H2C11B 0.7617 0.7311 0.4514 0.095 Uani H 1.0 H3C11B 0.5680 0.7409 0.5105 0.098 Uani H 1.0 H1C12B 0.3173 0.7943 0.1112 0.071 Uani H 1.0 H2C12B 0.4692 0.6980 0.1124 0.061 Uani H 1.0 H1C13B 0.4675 0.8613 0.2130 0.060 Uani H 1.0 H1C14B 0.7624 0.8082 0.2182 0.072 Uani H 1.0 H2C14B 0.7582 0.7157 0.1599 0.072 Uani H 1.0 H1C15B 0.6768 0.9094 0.0968 0.098 Uani H 1.0 H2C15B 0.6478 0.8223 0.0378 0.099 Uani H 1.0 H3C15B 0.4861 0.9114 0.0626 0.099 Uani H 1.0 H1O1G1 0.2293 0.5757 -0.0266 0.077 Uani H 1.0 H1C1G1 0.0272 0.4683 0.0849 0.219 Uani H 1.0 H2C1G1 0.1533 0.4342 -0.0064 0.219 Uani H 1.0 H1O1G2 0.3841 0.9459 0.3579 0.080 Uani H 1.0 H1O2G2 0.1400 1.0263 0.6297 0.091 Uani H 1.0 H1C1G2 0.1821 1.1162 0.4269 0.100 Uani H 1.0 H2C1G2 0.3926 1.0817 0.4320 0.100 Uani H 1.0 H1C2G2 0.3416 0.9482 0.5151 0.094 Uani H 1.0 H2C2G2 0.1323 0.9731 0.5037 0.094 Uani H 1.0 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1A 0.057(1) 0.049(1) 0.064(1) -0.0114(8) -0.0064(9) 0.0049(8) O O2A 0.059(2) 0.056(1) 0.064(2) -0.009(1) -0.007(1) 0.009(1) O C1A 0.065(1) 0.055(1) 0.059(2) -0.010(1) -0.013(1) -0.014(1) C C2A 0.054(1) 0.057(1) 0.041(1) -0.0088(8) -0.0017(8) -0.0043(7) C C3A 0.048(1) 0.049(1) 0.046(1) -0.0101(7) -0.0020(8) -0.0013(7) C C4A 0.049(1) 0.054(1) 0.044(1) -0.0077(8) 0.002(1) -0.0039(8) C C5A 0.049(1) 0.058(1) 0.054(1) -0.0144(9) 0.001(1) 0.007(1) C C6A 0.056(1) 0.046(1) 0.063(2) -0.0139(9) -0.0078(9) -0.0019(8) C C7A 0.054(1) 0.048(1) 0.057(1) -0.0069(8) -0.0039(8) -0.0035(8) C C8A 0.046(1) 0.055(1) 0.050(1) -0.0091(8) 0.0006(8) -0.0009(8) C C9A 0.050(1) 0.063(1) 0.046(1) -0.0086(9) 0.005(1) 0.0015(8) C C10A 0.051(1) 0.062(2) 0.060(2) -0.0098(9) -0.009(1) 0.002(1) C C11A 0.075(2) 0.057(1) 0.081(2) 0.006(2) -0.009(2) -0.017(1) C C12A 0.065(1) 0.060(1) 0.051(1) -0.0040(9) -0.006(1) -0.015(1) C C13A 0.068(2) 0.065(1) 0.054(1) -0.009(1) -0.014(1) -0.013(1) C C14A 0.053(1) 0.058(1) 0.062(2) -0.015(1) -0.012(1) -0.002(1) C C15A 0.106(4) 0.090(3) 0.085(2) -0.007(3) -0.042(3) -0.032(2) C O1B 0.059(1) 0.051(1) 0.066(2) -0.002(1) -0.015(1) -0.0162(9) O O2B 0.067(2) 0.056(1) 0.070(1) -0.004(1) -0.020(1) -0.018(1) O C1B 0.094(2) 0.066(2) 0.056(1) -0.020(1) -0.010(1) -0.002(1) C C2B 0.067(2) 0.049(1) 0.063(1) -0.0053(9) -0.018(1) -0.0042(9) C C3B 0.051(1) 0.049(1) 0.062(1) -0.0047(9) -0.0108(9) -0.0101(7) C C4B 0.046(1) 0.050(1) 0.064(1) 0.0004(9) -0.0134(9) -0.0120(8) C C5B 0.048(1) 0.058(1) 0.069(1) -0.001(1) -0.003(1) -0.019(1) C C6B 0.071(2) 0.062(1) 0.054(1) -0.010(1) -0.005(1) -0.0131(9) C C7B 0.068(2) 0.056(1) 0.061(1) -0.0040(9) -0.022(1) -0.0116(8) C C8B 0.049(1) 0.054(1) 0.076(1) 0.0008(9) -0.0203(9) -0.0142(8) C C9B 0.056(2) 0.050(1) 0.078(2) 0.005(1) -0.025(1) -0.0123(9) C C10B 0.062(2) 0.066(2) 0.090(2) -0.019(2) -0.006(1) -0.015(2) C C11B 0.118(4) 0.074(3) 0.077(2) -0.010(2) -0.051(2) -0.009(2) C C12B 0.065(1) 0.052(1) 0.056(2) -0.0046(9) -0.017(1) -0.006(1) C C13B 0.068(2) 0.054(1) 0.060(2) -0.012(1) -0.010(1) -0.005(1) C C14B 0.051(1) 0.062(2) 0.075(2) -0.010(1) -0.0029(9) -0.015(1) C C15B 0.124(4) 0.077(2) 0.070(2) -0.038(2) -0.007(2) 0.004(2) C O1G1 0.078(3) 0.100(4) 0.074(3) -0.063(3) -0.025(3) 0.011(3) O C1G1 0.194(9) 0.315(9) 0.177(9) -0.113(9) -0.089(7) 0.096(8) C O1G2 0.083(3) 0.073(3) 0.086(4) 0.008(3) -0.035(3) -0.030(3) O O2G2 0.099(4) 0.125(4) 0.064(3) -0.064(3) -0.009(3) 0.007(3) O C1G2 0.126(8) 0.091(6) 0.090(6) -0.025(5) -0.037(6) 0.009(5) C C2G2 0.094(6) 0.116(7) 0.082(6) -0.047(5) -0.019(5) 0.013(5) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C3A 1.454(6) 1_555 1_555 no O2A C7A 1.442(6) 1_555 1_555 no C1A C2A 1.509(8) 1_555 1_555 no C1A C6A 1.533(8) 1_555 1_555 no C2A C3A 1.513(7) 1_555 1_555 no C2A C9A 1.528(7) 1_555 1_555 no C3A C4A 1.545(8) 1_555 1_555 no C3A C10A 1.521(8) 1_555 1_555 no C4A C5A 1.546(7) 1_555 1_555 no C4A C12A 1.541(8) 1_555 1_555 no C5A C6A 1.539(8) 1_555 1_555 no C6A C7A 1.537(8) 1_555 1_555 no C7A C8A 1.528(7) 1_555 1_555 no C7A C11A 1.537(8) 1_555 1_555 no C8A C9A 1.548(7) 1_555 1_555 no C8A C14A 1.540(8) 1_555 1_555 no C12A C13A 1.471(8) 1_555 1_555 no C13A C14A 1.477(8) 1_555 1_555 no C13A C15A 1.543(8) 1_555 1_555 no O1B C3B 1.461(6) 1_555 1_555 no O2B C7B 1.444(7) 1_555 1_555 no C1B C2B 1.540(8) 1_555 1_555 no C1B C6B 1.522(8) 1_555 1_555 no C2B C3B 1.508(8) 1_555 1_555 no C2B C9B 1.533(8) 1_555 1_555 no C3B C4B 1.529(7) 1_555 1_555 no C3B C10B 1.532(8) 1_555 1_555 no C4B C5B 1.557(8) 1_555 1_555 no C4B C12B 1.551(8) 1_555 1_555 no C5B C6B 1.532(8) 1_555 1_555 no C6B C7B 1.515(8) 1_555 1_555 no C7B C8B 1.542(8) 1_555 1_555 no C7B C11B 1.541(8) 1_555 1_555 no C8B C9B 1.536(8) 1_555 1_555 no C8B C14B 1.542(8) 1_555 1_555 no C12B C13B 1.526(8) 1_555 1_555 no C13B C14B 1.508(8) 1_555 1_555 no C13B C15B 1.525(9) 1_555 1_555 no O1G2 C1G2 1.410(9) 1_555 1_555 no O2G2 C2G2 1.520(9) 1_555 1_555 no C1G2 C2G2 1.420(10) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A C1A C6A 107.9(5) 1_555 1_555 1_555 no C1A C2A C3A 110.7(5) 1_555 1_555 1_555 no C1A C2A C9A 108.8(5) 1_555 1_555 1_555 no C3A C2A C9A 117.3(5) 1_555 1_555 1_555 no O1A C3A C2A 106.5(4) 1_555 1_555 1_555 no O1A C3A C4A 111.0(4) 1_555 1_555 1_555 no O1A C3A C10A 106.0(4) 1_555 1_555 1_555 no C2A C3A C4A 113.4(5) 1_555 1_555 1_555 no C2A C3A C10A 110.2(5) 1_555 1_555 1_555 no C4A C3A C10A 109.5(4) 1_555 1_555 1_555 no C3A C4A C5A 111.6(5) 1_555 1_555 1_555 no C3A C4A C12A 116.3(5) 1_555 1_555 1_555 no C5A C4A C12A 114.8(5) 1_555 1_555 1_555 no C4A C5A C6A 118.9(5) 1_555 1_555 1_555 no C1A C6A C5A 107.4(5) 1_555 1_555 1_555 no C1A C6A C7A 109.7(5) 1_555 1_555 1_555 no C5A C6A C7A 117.7(5) 1_555 1_555 1_555 no O2A C7A C6A 105.3(4) 1_555 1_555 1_555 no O2A C7A C8A 112.0(5) 1_555 1_555 1_555 no O2A C7A C11A 106.4(5) 1_555 1_555 1_555 no C6A C7A C8A 113.6(5) 1_555 1_555 1_555 no C6A C7A C11A 109.9(5) 1_555 1_555 1_555 no C8A C7A C11A 109.3(5) 1_555 1_555 1_555 no C7A C8A C9A 111.6(5) 1_555 1_555 1_555 no C7A C8A C14A 117.0(5) 1_555 1_555 1_555 no C9A C8A C14A 115.6(5) 1_555 1_555 1_555 no C2A C9A C8A 118.4(5) 1_555 1_555 1_555 no C4A C12A C13A 122.5(5) 1_555 1_555 1_555 no C12A C13A C14A 121.8(5) 1_555 1_555 1_555 no C12A C13A C15A 109.2(5) 1_555 1_555 1_555 no C14A C13A C15A 108.8(5) 1_555 1_555 1_555 no C8A C14A C13A 123.8(5) 1_555 1_555 1_555 no C2B C1B C6B 107.6(5) 1_555 1_555 1_555 no C1B C2B C3B 109.0(5) 1_555 1_555 1_555 no C1B C2B C9B 107.8(5) 1_555 1_555 1_555 no C3B C2B C9B 117.4(5) 1_555 1_555 1_555 no O1B C3B C2B 104.9(4) 1_555 1_555 1_555 no O1B C3B C4B 111.5(5) 1_555 1_555 1_555 no O1B C3B C10B 105.3(4) 1_555 1_555 1_555 no C2B C3B C4B 113.9(5) 1_555 1_555 1_555 no C2B C3B C10B 111.2(5) 1_555 1_555 1_555 no C4B C3B C10B 109.7(5) 1_555 1_555 1_555 no C3B C4B C5B 110.8(5) 1_555 1_555 1_555 no C3B C4B C12B 116.0(5) 1_555 1_555 1_555 no C5B C4B C12B 115.4(5) 1_555 1_555 1_555 no C4B C5B C6B 117.8(5) 1_555 1_555 1_555 no C1B C6B C5B 107.8(5) 1_555 1_555 1_555 no C1B C6B C7B 109.9(5) 1_555 1_555 1_555 no C5B C6B C7B 119.7(5) 1_555 1_555 1_555 no O2B C7B C6B 106.8(5) 1_555 1_555 1_555 no O2B C7B C8B 111.1(5) 1_555 1_555 1_555 no O2B C7B C11B 106.4(5) 1_555 1_555 1_555 no C6B C7B C8B 113.1(5) 1_555 1_555 1_555 no C6B C7B C11B 110.7(6) 1_555 1_555 1_555 no C8B C7B C11B 108.5(5) 1_555 1_555 1_555 no C7B C8B C9B 111.6(5) 1_555 1_555 1_555 no C7B C8B C14B 116.0(5) 1_555 1_555 1_555 no C9B C8B C14B 116.2(5) 1_555 1_555 1_555 no C2B C9B C8B 120.5(5) 1_555 1_555 1_555 no C4B C12B C13B 120.9(5) 1_555 1_555 1_555 no C12B C13B C14B 115.7(5) 1_555 1_555 1_555 no C12B C13B C15B 108.5(5) 1_555 1_555 1_555 no C14B C13B C15B 108.9(6) 1_555 1_555 1_555 no C8B C14B C13B 121.8(5) 1_555 1_555 1_555 no O1G2 C1G2 C2G2 110.4(7) 1_555 1_555 1_555 no O2G2 C2G2 C1G2 107.4(7) 1_555 1_555 1_555 no 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 C6A C1A C2A C3A -68.7(6) 1_555 1_555 1_555 1_555 no C6A C1A C2A C9A 61.6(6) 1_555 1_555 1_555 1_555 no C2A C1A C6A C5A 61.7(6) 1_555 1_555 1_555 1_555 no C2A C1A C6A C7A -67.2(6) 1_555 1_555 1_555 1_555 no C1A C2A C3A O1A 179.1(4) 1_555 1_555 1_555 1_555 no C1A C2A C3A C4A 56.7(6) 1_555 1_555 1_555 1_555 no C1A C2A C3A C10A -66.4(6) 1_555 1_555 1_555 1_555 no C9A C2A C3A O1A 53.4(6) 1_555 1_555 1_555 1_555 no C9A C2A C3A C4A -68.9(6) 1_555 1_555 1_555 1_555 no C9A C2A C3A C10A 167.9(5) 1_555 1_555 1_555 1_555 no C1A C2A C9A C8A -49.1(7) 1_555 1_555 1_555 1_555 no C3A C2A C9A C8A 77.5(7) 1_555 1_555 1_555 1_555 no O1A C3A C4A C5A -158.9(4) 1_555 1_555 1_555 1_555 no O1A C3A C4A C12A -24.5(6) 1_555 1_555 1_555 1_555 no C2A C3A C4A C5A -39.0(6) 1_555 1_555 1_555 1_555 no C2A C3A C4A C12A 95.3(6) 1_555 1_555 1_555 1_555 no C10A C3A C4A C5A 84.4(6) 1_555 1_555 1_555 1_555 no C10A C3A C4A C12A -141.2(5) 1_555 1_555 1_555 1_555 no C3A C4A C5A C6A 37.0(7) 1_555 1_555 1_555 1_555 no C12A C4A C5A C6A -98.0(6) 1_555 1_555 1_555 1_555 no C3A C4A C12A C13A -98.7(7) 1_555 1_555 1_555 1_555 no C5A C4A C12A C13A 34.2(8) 1_555 1_555 1_555 1_555 no C4A C5A C6A C1A -48.4(6) 1_555 1_555 1_555 1_555 no C4A C5A C6A C7A 75.8(7) 1_555 1_555 1_555 1_555 no C1A C6A C7A O2A 179.6(4) 1_555 1_555 1_555 1_555 no C1A C6A C7A C8A 56.7(6) 1_555 1_555 1_555 1_555 no C1A C6A C7A C11A -66.1(6) 1_555 1_555 1_555 1_555 no C5A C6A C7A O2A 56.5(6) 1_555 1_555 1_555 1_555 no C5A C6A C7A C8A -66.4(7) 1_555 1_555 1_555 1_555 no C5A C6A C7A C11A 170.8(5) 1_555 1_555 1_555 1_555 no O2A C7A C8A C9A -159.7(5) 1_555 1_555 1_555 1_555 no O2A C7A C8A C14A -23.4(7) 1_555 1_555 1_555 1_555 no C6A C7A C8A C9A -40.6(6) 1_555 1_555 1_555 1_555 no C6A C7A C8A C14A 95.8(6) 1_555 1_555 1_555 1_555 no C11A C7A C8A C9A 82.6(6) 1_555 1_555 1_555 1_555 no C11A C7A C8A C14A -141.1(5) 1_555 1_555 1_555 1_555 no C7A C8A C9A C2A 38.0(7) 1_555 1_555 1_555 1_555 no C14A C8A C9A C2A -99.0(6) 1_555 1_555 1_555 1_555 no C7A C8A C14A C13A -51.9(8) 1_555 1_555 1_555 1_555 no C9A C8A C14A C13A 82.7(7) 1_555 1_555 1_555 1_555 no C4A C12A C13A C14A 58.8(8) 1_555 1_555 1_555 1_555 no C4A C12A C13A C15A -173.0(5) 1_555 1_555 1_555 1_555 no C12A C13A C14A C8A -51.1(8) 1_555 1_555 1_555 1_555 no C15A C13A C14A C8A -179.4(5) 1_555 1_555 1_555 1_555 no C6B C1B C2B C3B -68.6(6) 1_555 1_555 1_555 1_555 no C6B C1B C2B C9B 59.9(6) 1_555 1_555 1_555 1_555 no C2B C1B C6B C5B 62.5(6) 1_555 1_555 1_555 1_555 no C2B C1B C6B C7B -69.6(6) 1_555 1_555 1_555 1_555 no C1B C2B C3B O1B -179.0(4) 1_555 1_555 1_555 1_555 no C1B C2B C3B C4B 58.8(7) 1_555 1_555 1_555 1_555 no C1B C2B C3B C10B -65.7(6) 1_555 1_555 1_555 1_555 no C9B C2B C3B O1B 58.2(6) 1_555 1_555 1_555 1_555 no C9B C2B C3B C4B -64.0(7) 1_555 1_555 1_555 1_555 no C9B C2B C3B C10B 171.5(5) 1_555 1_555 1_555 1_555 no C1B C2B C9B C8B -45.4(7) 1_555 1_555 1_555 1_555 no C3B C2B C9B C8B 78.0(7) 1_555 1_555 1_555 1_555 no O1B C3B C4B C5B -161.5(4) 1_555 1_555 1_555 1_555 no O1B C3B C4B C12B -27.5(6) 1_555 1_555 1_555 1_555 no C2B C3B C4B C5B -43.0(7) 1_555 1_555 1_555 1_555 no C2B C3B C4B C12B 91.0(6) 1_555 1_555 1_555 1_555 no C10B C3B C4B C5B 82.3(6) 1_555 1_555 1_555 1_555 no C10B C3B C4B C12B -143.7(5) 1_555 1_555 1_555 1_555 no C3B C4B C5B C6B 39.8(7) 1_555 1_555 1_555 1_555 no C12B C4B C5B C6B -94.5(6) 1_555 1_555 1_555 1_555 no C3B C4B C12B C13B -107.4(6) 1_555 1_555 1_555 1_555 no C5B C4B C12B C13B 24.5(7) 1_555 1_555 1_555 1_555 no C4B C5B C6B C1B -50.4(7) 1_555 1_555 1_555 1_555 no C4B C5B C6B C7B 76.1(7) 1_555 1_555 1_555 1_555 no C1B C6B C7B O2B -178.6(5) 1_555 1_555 1_555 1_555 no C1B C6B C7B C8B 58.8(7) 1_555 1_555 1_555 1_555 no C1B C6B C7B C11B -63.2(6) 1_555 1_555 1_555 1_555 no C5B C6B C7B O2B 55.9(7) 1_555 1_555 1_555 1_555 no C5B C6B C7B C8B -66.7(7) 1_555 1_555 1_555 1_555 no C5B C6B C7B C11B 171.3(5) 1_555 1_555 1_555 1_555 no O2B C7B C8B C9B -159.5(4) 1_555 1_555 1_555 1_555 no O2B C7B C8B C14B -23.4(7) 1_555 1_555 1_555 1_555 no C6B C7B C8B C9B -39.4(7) 1_555 1_555 1_555 1_555 no C6B C7B C8B C14B 96.7(6) 1_555 1_555 1_555 1_555 no C11B C7B C8B C9B 83.8(6) 1_555 1_555 1_555 1_555 no C11B C7B C8B C14B -140.1(5) 1_555 1_555 1_555 1_555 no C7B C8B C9B C2B 34.8(7) 1_555 1_555 1_555 1_555 no C14B C8B C9B C2B -101.2(7) 1_555 1_555 1_555 1_555 no C7B C8B C14B C13B -50.6(8) 1_555 1_555 1_555 1_555 no C9B C8B C14B C13B 83.6(7) 1_555 1_555 1_555 1_555 no C4B C12B C13B C14B 71.3(7) 1_555 1_555 1_555 1_555 no C4B C12B C13B C15B -165.9(5) 1_555 1_555 1_555 1_555 no C12B C13B C14B C8B -57.2(8) 1_555 1_555 1_555 1_555 no C15B C13B C14B C8B -179.8(5) 1_555 1_555 1_555 1_555 no O1G2 C1G2 C2G2 O2G2 -174.1(5) 1_555 1_555 1_555 1_555 no # Attachment 'drb283.cif' data_drb283 _database_code_depnum_ccdc_archive 'CCDC 295349' _audit_creation_method 'RAELSPUB and manual entry' _publ_section_abstract ? _publ_section_comment ? _publ_section_acknowledgements ? _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435. Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974. Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee, U.S.A., 1976. Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1996. ; _publ_section_figure_captions ? _publ_section_exptl_prep ? _publ_section_exptl_refinement ? _computing_data_collection 'CAD4 Version 5.0, 1989' _computing_cell_refinement 'CAD4 Version 5.0, 1989' _computing_data_reduction 'Local program' _computing_structure_solution 'SIR92 (Altomare et al,1994)' _computing_structure_refinement 'RAELS, (Rae, 1996)' _computing_molecular_graphics 'ORTEP-II, (Johnson, 1976)' _computing_publication_material 'Local programs' # CHEMICAL DATA _chemical_name_systematic ? _chemical_formula_moiety 'C15 H26 O2, C4 H10 O' _chemical_formula_sum 'C19 H36 O3' _chemical_formula_iupac ? _chemical_formula_weight 312.5 _chemical_absolute_configuration ? # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 6.991(4) _cell_length_b 13.781(6) _cell_length_c 20.216(8) _cell_angle_alpha 90 _cell_angle_beta 97.60(3) _cell_angle_gamma 90 _cell_volume 1931(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _cell_measurement_temperature 294 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_size_rad 0.15 _exptl_crystal_density_diffrn 1.07 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696.0 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_reflns_number 2769 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_theta_max 23 _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 23 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 1 _diffrn_standards_interval_time 30min _diffrn_standards_decay_% 32 # REFINEMENT DATA _refine_special_details ? _reflns_number_total 2683 _reflns_number_gt 1124 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.107 _refine_ls_wR_factor_ref 0.136 _refine_ls_abs_structure_Flack ? _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1124 _refine_ls_number_parameters 114 _refine_ls_goodness_of_fit_ref 1.99 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F^2^]' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.73 _refine_diff_density_min -0.56 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _atom_type_scat_source 'International Tables for X-ray Crystallography, Vol. IV' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_type_symbol _atom_site_occupancy O1 0.8697(8) -0.0400(4) 0.1829(4) 0.068(2) Uani O 1.0 O2 0.7998(9) 0.3352(5) 0.2935(4) 0.080(3) Uani O 1.0 C1 0.8042(14) 0.2177(7) 0.1292(6) 0.068(2) Uani C 1.0 C2 0.7499(12) 0.1143(7) 0.1456(5) 0.059(2) Uani C 1.0 C3 0.9317(12) 0.0564(7) 0.1705(5) 0.056(2) Uani C 1.0 C4 1.0514(12) 0.1013(7) 0.2312(6) 0.058(2) Uani C 1.0 C5 1.0604(12) 0.2146(6) 0.2251(6) 0.063(2) Uani C 1.0 C6 0.8792(13) 0.2680(7) 0.1926(6) 0.064(2) Uani C 1.0 C7 0.7204(12) 0.2843(7) 0.2343(6) 0.065(2) Uani C 1.0 C8 0.6160(12) 0.1875(7) 0.2510(6) 0.062(2) Uani C 1.0 C9 0.5881(12) 0.1192(7) 0.1891(5) 0.062(2) Uani C 1.0 C10 1.0570(13) 0.0480(7) 0.1136(6) 0.068(2) Uani C 1.0 C11 0.5664(14) 0.3546(7) 0.1990(6) 0.083(3) Uani C 1.0 C12 1.0206(14) 0.0664(8) 0.2985(6) 0.074(1) Uani C 1.0 C13 0.8239(20) 0.0535(11) 0.3221(7) 0.085(2) Uani C 0.77 C13' 0.8933(33) 0.1098(35) 0.3466(11) 0.089(2) Uani C 0.23 C14 0.6919(15) 0.1406(8) 0.3186(6) 0.078(2) Uani C 1.0 C15 0.8578(39) 0.0279(18) 0.3975(8) 0.132(5) Uani C 0.77 C15' 0.8539(90) 0.0058(40) 0.3726(32) 0.120(4) Uani C 0.23 O1Bu 0.4882(10) 0.3738(6) 0.3663(5) 0.096(3) Uani O 1.0 C1Bu 0.5213(18) 0.3713(10) 0.4363(7) 0.112(5) Uani C 1.0 C2Bu 0.3610(25) 0.3437(13) 0.4746(9) 0.126(6) Uani C 0.67 C3Bu 0.2796(32) 0.2463(18) 0.4566(17) 0.254(9) Uani C 0.67 C4Bu 0.3943(48) 0.1663(22) 0.4858(16) 0.251(9) Uani C 0.67 C2'Bu 0.4593(38) 0.2772(17) 0.4635(19) 0.126(6) Uani C 0.33 C3'Bu 0.2464(48) 0.2685(38) 0.4571(31) 0.254(9) Uani C 0.33 C4'Bu 0.1844(78) 0.2050(54) 0.5074(30) 0.251(9) Uani C 0.33 H1O1 0.9849 -0.0835 0.1911 0.076 Uani H 1.0 H1O2 0.6899 0.3488 0.3191 0.089 Uani H 1.0 H1C1 0.6879 0.2526 0.1069 0.082 Uani H 1.0 H2C1 0.9061 0.2165 0.0989 0.079 Uani H 1.0 HC2 0.6934 0.0839 0.1025 0.072 Uani H 1.0 HC4 1.1861 0.0802 0.2270 0.065 Uani H 1.0 H1C5 1.1670 0.2302 0.1984 0.074 Uani H 1.0 H2C5 1.0928 0.2411 0.2713 0.073 Uani H 1.0 HC6 0.9226 0.3337 0.1798 0.082 Uani H 1.0 HC8 0.4918 0.2004 0.2690 0.073 Uani H 1.0 H1C9 0.4690 0.1410 0.1600 0.072 Uani H 1.0 H2C9 0.5684 0.0521 0.2057 0.069 Uani H 1.0 H1C10 1.1045 0.1138 0.1028 0.075 Uani H 1.0 H2C10 1.1695 0.0046 0.1278 0.072 Uani H 1.0 H3C10 0.9781 0.0202 0.0732 0.080 Uani H 1.0 H1C11 0.5032 0.3242 0.1568 0.086 Uani H 1.0 H2C11 0.4669 0.3681 0.2291 0.088 Uani H 1.0 H3C11 0.6297 0.4167 0.1885 0.099 Uani H 1.0 H1C12 1.0924 0.1130 0.3307 0.086 Uani H 0.77 H2C12 1.0837 0.0013 0.3035 0.087 Uani H 0.77 H1'C12 1.1527 0.0651 0.3245 0.090 Uani H 0.23 H2'C12 0.9722 -0.0015 0.2910 0.081 Uani H 0.23 HC13 0.7547 -0.0015 0.2970 0.087 Uani H 0.77 HC13' 0.9612 0.1546 0.3809 0.105 Uani H 0.23 H1C14 0.7633 0.1924 0.3463 0.085 Uani H 0.77 H2C14 0.5760 0.1205 0.3394 0.095 Uani H 0.77 H1'C14 0.6542 0.1874 0.3524 0.091 Uani H 0.23 H2'C14 0.6139 0.0799 0.3195 0.089 Uani H 0.23 H1C15 0.7306 0.0190 0.4143 0.150 Uani H 0.77 H2C15 0.9341 -0.0336 0.4041 0.150 Uani H 0.77 H3C15 0.9306 0.0817 0.4228 0.139 Uani H 0.77 H1C15' 0.7667 0.0104 0.4079 0.146 Uani H 0.23 H2C15' 0.7911 -0.0347 0.3348 0.111 Uani H 0.23 H3C15' 0.9788 -0.0247 0.3918 0.139 Uani H 0.23 H1O1Bu 0.3617 0.4043 0.3489 0.096 Uani H 1.0 H1C1Bu 0.5643 0.4378 0.4515 0.112 Uani H 0.67 H2C1Bu 0.6285 0.3241 0.4489 0.112 Uani H 0.67 H1C2Bu 0.2556 0.3928 0.4655 0.126 Uani H 0.67 H2C2Bu 0.4114 0.3440 0.5232 0.126 Uani H 0.67 H1C3Bu 0.2665 0.2395 0.4069 0.254 Uani H 0.67 H2C3Bu 0.1492 0.2422 0.4716 0.254 Uani H 0.67 H1C4Bu 0.3296 0.1037 0.4713 0.251 Uani H 0.67 H2C4Bu 0.5250 0.1686 0.4709 0.251 Uani H 0.67 H3C4Bu 0.4077 0.1713 0.5356 0.251 Uani H 0.67 H1'C1Bu 0.4473 0.4253 0.4542 0.112 Uani H 0.33 H2'C1Bu 0.6623 0.3806 0.4511 0.112 Uani H 0.33 H1C2'Bu 0.5130 0.2727 0.5117 0.126 Uani H 0.33 H2C2'Bu 0.5112 0.2228 0.4384 0.126 Uani H 0.33 H1C3'Bu 0.1982 0.2418 0.4120 0.254 Uani H 0.33 H2C3'Bu 0.1900 0.3344 0.4619 0.254 Uani H 0.33 H1C4'Bu 0.0403 0.2012 0.5013 0.251 Uani H 0.33 H2C4'Bu 0.2392 0.1387 0.5029 0.251 Uani H 0.33 H3C4'Bu 0.2310 0.2313 0.5528 0.251 Uani H 0.33 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol O1 0.037(2) 0.040(2) 0.127(4) 0.000(1) 0.008(2) -0.003(2) O O2 0.037(3) 0.062(3) 0.139(4) 0.001(2) 0.004(3) -0.031(3) O C1 0.051(2) 0.054(2) 0.098(3) 0.010(2) 0.005(2) 0.015(2) C C2 0.032(2) 0.050(2) 0.091(3) 0.004(1) -0.002(2) -0.002(2) C C3 0.029(2) 0.042(2) 0.095(3) 0.001(1) 0.002(1) -0.001(2) C C4 0.030(2) 0.046(2) 0.095(3) 0.004(2) -0.002(2) 0.000(2) C C5 0.030(2) 0.045(2) 0.114(3) -0.002(2) 0.005(2) -0.008(2) C C6 0.039(2) 0.039(2) 0.115(3) 0.001(2) 0.009(2) 0.005(2) C C7 0.033(2) 0.043(2) 0.116(3) 0.003(1) 0.003(2) -0.006(2) C C8 0.032(2) 0.050(2) 0.104(3) 0.000(1) 0.008(2) -0.005(2) C C9 0.028(2) 0.047(2) 0.108(3) 0.000(1) 0.002(2) -0.007(2) C C10 0.039(2) 0.062(3) 0.103(4) 0.002(2) 0.010(2) -0.010(2) C C11 0.047(3) 0.048(3) 0.150(6) 0.014(3) 0.002(3) -0.001(3) C C12 0.055(2) 0.070(3) 0.094(3) 0.017(2) -0.004(2) 0.010(2) C C13 0.076(4) 0.079(3) 0.101(3) 0.014(3) 0.018(3) 0.023(3) C C13' 0.076(4) 0.099(4) 0.089(3) 0.020(4) 0.005(2) 0.010(2) C C14 0.059(3) 0.077(3) 0.099(3) 0.005(3) 0.019(2) 0.004(3) C C15 0.144(9) 0.147(7) 0.108(3) 0.039(7) 0.030(5) 0.047(5) C C15' 0.129(8) 0.121(6) 0.115(3) 0.032(6) 0.031(5) 0.048(5) C O1Bu 0.062(5) 0.092(6) 0.133(8) 0.023(4) 0.004(5) 0.019(7) O C1Bu 0.104(9) 0.105(9) 0.123(9) 0.006(9) 0.001(9) -0.005(9) C C2Bu 0.110(6) 0.148(6) 0.115(6) 0.0229(0) -0.0007(8) -0.0054(0) C C3Bu 0.239(9) 0.215(9) 0.281(9) -0.0018(0) -0.061(1) -0.0514(1) C C4Bu 0.244(9) 0.320(9) 0.192(9) -0.1044(1) 0.039(2) 0.0169(0) C C2'Bu 0.110(6) 0.148(6) 0.115(6) 0.0229(0) -0.0007(8) -0.0054(0) C C3'Bu 0.239(9) 0.215(9) 0.281(9) -0.0018(0) -0.061(1) -0.0514(1) C C4'Bu 0.244(9) 0.320(9) 0.192(9) -0.1044(1) 0.039(2) 0.0169(0) C # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.429(10) 1_555 1_555 no O2 C7 1.434(11) 1_555 1_555 no C1 C2 1.523(13) 1_555 1_555 no C1 C6 1.490(14) 1_555 1_555 no C2 C3 1.529(12) 1_555 1_555 no C2 C9 1.523(13) 1_555 1_555 no C3 C4 1.522(13) 1_555 1_555 no C3 C10 1.540(13) 1_555 1_555 no C4 C5 1.568(12) 1_555 1_555 no C4 C12 1.487(13) 1_555 1_555 no C5 C6 1.536(12) 1_555 1_555 no C6 C7 1.497(13) 1_555 1_555 no C7 C8 1.578(13) 1_555 1_555 no C7 C11 1.550(13) 1_555 1_555 no C8 C9 1.558(13) 1_555 1_555 no C8 C14 1.541(14) 1_555 1_555 no C12 C13 1.524(15) 1_555 1_555 no C12 C13' 1.523(17) 1_555 1_555 no C13 C14 1.509(16) 1_555 1_555 no C13 C15 1.552(9) 1_555 1_555 no C13' C14 1.507(18) 1_555 1_555 no C13' C15' 1.564(20) 1_555 1_555 no O1Bu C1Bu 1.404(13) 1_555 1_555 no C1Bu C2Bu 1.493(8) 1_555 1_555 no C1Bu C2'Bu 1.495(14) 1_555 1_555 no C2Bu C3Bu 1.485(16) 1_555 1_555 no C3Bu C4Bu 1.443(25) 1_555 1_555 no C2'Bu C3'Bu 1.482(21) 1_555 1_555 no C3'Bu C4'Bu 1.451(44) 1_555 1_555 no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 108.5(9) 1_555 1_555 1_555 no C1 C2 C3 109.9(7) 1_555 1_555 1_555 no C1 C2 C9 108.0(8) 1_555 1_555 1_555 no C3 C2 C9 118.8(9) 1_555 1_555 1_555 no O1 C3 C2 106.5(7) 1_555 1_555 1_555 no O1 C3 C4 112.6(8) 1_555 1_555 1_555 no O1 C3 C10 106.1(8) 1_555 1_555 1_555 no C2 C3 C4 113.4(7) 1_555 1_555 1_555 no C2 C3 C10 108.8(8) 1_555 1_555 1_555 no C4 C3 C10 109.0(7) 1_555 1_555 1_555 no C3 C4 C5 111.5(8) 1_555 1_555 1_555 no C3 C4 C12 118.4(8) 1_555 1_555 1_555 no C5 C4 C12 113.9(9) 1_555 1_555 1_555 no C4 C5 C6 118.1(8) 1_555 1_555 1_555 no C1 C6 C5 108.7(8) 1_555 1_555 1_555 no C1 C6 C7 110.6(8) 1_555 1_555 1_555 no C5 C6 C7 117.5(9) 1_555 1_555 1_555 no O2 C7 C6 108.0(7) 1_555 1_555 1_555 no O2 C7 C8 111.9(9) 1_555 1_555 1_555 no O2 C7 C11 104.3(8) 1_555 1_555 1_555 no C6 C7 C8 113.2(8) 1_555 1_555 1_555 no C6 C7 C11 110.9(9) 1_555 1_555 1_555 no C8 C7 C11 108.3(7) 1_555 1_555 1_555 no C7 C8 C9 110.5(9) 1_555 1_555 1_555 no C7 C8 C14 115.5(8) 1_555 1_555 1_555 no C9 C8 C14 116.8(8) 1_555 1_555 1_555 no C2 C9 C8 117.9(7) 1_555 1_555 1_555 no C4 C12 C13 124.8(9) 1_555 1_555 1_555 no C4 C12 C13' 128.6(18) 1_555 1_555 1_555 no C12 C13 C14 117.6(11) 1_555 1_555 1_555 no C12 C13 C15 107.9(14) 1_555 1_555 1_555 no C14 C13 C15 103.9(14) 1_555 1_555 1_555 no C12 C13' C14 117.8(13) 1_555 1_555 1_555 no C12 C13' C15' 89.9(35) 1_555 1_555 1_555 no C14 C13' C15' 100.7(39) 1_555 1_555 1_555 no C8 C14 C13 120.9(10) 1_555 1_555 1_555 no C8 C14 C13' 130.3(16) 1_555 1_555 1_555 no O1Bu C1Bu C2Bu 119.6(12) 1_555 1_555 1_555 no O1Bu C1Bu C2'Bu 112.0(19) 1_555 1_555 1_555 no C1Bu C2Bu C3Bu 113.2(11) 1_555 1_555 1_555 no C2Bu C3Bu C4Bu 114.6(14) 1_555 1_555 1_555 no C1Bu C2'Bu C3'Bu 112.0(16) 1_555 1_555 1_555 no C2'Bu C3'Bu C4'Bu 112.2(18) 1_555 1_555 1_555 no 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 C6 C1 C2 C3 -68.2(10) 1_555 1_555 1_555 1_555 no C6 C1 C2 C9 62.8(10) 1_555 1_555 1_555 1_555 no C2 C1 C6 C5 61.5(10) 1_555 1_555 1_555 1_555 no C2 C1 C6 C7 -68.9(10) 1_555 1_555 1_555 1_555 no C1 C2 C3 O1 -178.3(8) 1_555 1_555 1_555 1_555 no C1 C2 C3 C4 57.2(11) 1_555 1_555 1_555 1_555 no C1 C2 C3 C10 -64.3(10) 1_555 1_555 1_555 1_555 no C9 C2 C3 O1 56.7(11) 1_555 1_555 1_555 1_555 no C9 C2 C3 C4 -67.8(11) 1_555 1_555 1_555 1_555 no C9 C2 C3 C10 170.6(8) 1_555 1_555 1_555 1_555 no C1 C2 C9 C8 -49.7(11) 1_555 1_555 1_555 1_555 no C3 C2 C9 C8 76.2(11) 1_555 1_555 1_555 1_555 no O1 C3 C4 C5 -161.4(7) 1_555 1_555 1_555 1_555 no O1 C3 C4 C12 -26.3(11) 1_555 1_555 1_555 1_555 no C2 C3 C4 C5 -40.3(11) 1_555 1_555 1_555 1_555 no C2 C3 C4 C12 94.8(10) 1_555 1_555 1_555 1_555 no C10 C3 C4 C5 81.1(9) 1_555 1_555 1_555 1_555 no C10 C3 C4 C12 -143.8(9) 1_555 1_555 1_555 1_555 no C3 C4 C5 C6 36.9(12) 1_555 1_555 1_555 1_555 no C12 C4 C5 C6 -100.3(11) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13 -47.4(15) 1_555 1_555 1_555 1_555 no C3 C4 C12 C13' -95.9(22) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13 86.7(13) 1_555 1_555 1_555 1_555 no C5 C4 C12 C13' 38.1(22) 1_555 1_555 1_555 1_555 no C4 C5 C6 C1 -47.8(12) 1_555 1_555 1_555 1_555 no C4 C5 C6 C7 78.7(12) 1_555 1_555 1_555 1_555 no C1 C6 C7 O2 -178.4(7) 1_555 1_555 1_555 1_555 no C1 C6 C7 C8 57.2(11) 1_555 1_555 1_555 1_555 no C1 C6 C7 C11 -64.7(10) 1_555 1_555 1_555 1_555 no C5 C6 C7 O2 56.0(11) 1_555 1_555 1_555 1_555 no C5 C6 C7 C8 -68.5(11) 1_555 1_555 1_555 1_555 no C5 C6 C7 C11 169.7(8) 1_555 1_555 1_555 1_555 no O2 C7 C8 C9 -162.5(7) 1_555 1_555 1_555 1_555 no O2 C7 C8 C14 -27.3(10) 1_555 1_555 1_555 1_555 no C6 C7 C8 C9 -40.2(10) 1_555 1_555 1_555 1_555 no C6 C7 C8 C14 95.0(11) 1_555 1_555 1_555 1_555 no C11 C7 C8 C9 83.1(10) 1_555 1_555 1_555 1_555 no C11 C7 C8 C14 -141.7(9) 1_555 1_555 1_555 1_555 no C7 C8 C9 C2 38.3(11) 1_555 1_555 1_555 1_555 no C14 C8 C9 C2 -96.3(11) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13 -102.2(12) 1_555 1_555 1_555 1_555 no C7 C8 C14 C13' -54.9(24) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13 30.2(13) 1_555 1_555 1_555 1_555 no C9 C8 C14 C13' 77.5(24) 1_555 1_555 1_555 1_555 no C4 C12 C13 C14 -56.4(17) 1_555 1_555 1_555 1_555 no C4 C12 C13 C15 -173.4(14) 1_555 1_555 1_555 1_555 no C4 C12 C13' C14 45.4(45) 1_555 1_555 1_555 1_555 no C4 C12 C13' C15' 147.5(32) 1_555 1_555 1_555 1_555 no C12 C13 C14 C8 63.1(16) 1_555 1_555 1_555 1_555 no C15 C13 C14 C8 -177.8(13) 1_555 1_555 1_555 1_555 no C12 C13' C14 C8 -37.0(47) 1_555 1_555 1_555 1_555 no C15' C13' C14 C8 -132.6(29) 1_555 1_555 1_555 1_555 no O1Bu C1Bu C2Bu C3Bu 57.8(20) 1_555 1_555 1_555 1_555 no O1Bu C1Bu C2'Bu C3'Bu -72.7(38) 1_555 1_555 1_555 1_555 no C1Bu C2Bu C3Bu C4Bu 78.2(31) 1_555 1_555 1_555 1_555 no C1Bu C2'Bu C3'Bu C4'Bu -153.4(50) 1_555 1_555 1_555 1_555 no