# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Mark Peczuh' _publ_contact_author_email MARK.PECZUH@UCONN.EDU _publ_section_title ; Asymmetric toggling of [13] macro-dilactone topology by a single stereogenic center ; loop_ _publ_author_name 'Mark Peczuh' 'W. Sean Fyvie' # Attachment 'uconn_mp07.cif' data_mp07 _database_code_depnum_ccdc_archive 'CCDC 686765' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 O5' _chemical_formula_weight 282.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.0375(14) _cell_length_b 11.004(2) _cell_length_c 9.6494(19) _cell_angle_alpha 90.00 _cell_angle_beta 102.95(3) _cell_angle_gamma 90.00 _cell_volume 728.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9718 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3617 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 28.98 _reflns_number_total 3617 _reflns_number_gt 2167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(10) _refine_ls_number_reflns 3617 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1130 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0967(2) 0.84706(13) 0.25644(13) 0.0302(4) Uani 1 1 d . . . O2 O 0.0525(2) 0.95614(13) 0.44346(14) 0.0386(4) Uani 1 1 d . . . O3 O 0.3649(2) 0.79554(14) 0.82028(13) 0.0412(4) Uani 1 1 d . . . O4 O 0.5572(2) 0.76125(14) 0.44255(14) 0.0406(4) Uani 1 1 d . . . O5 O 0.5322(2) 0.93272(12) 0.31382(14) 0.0345(4) Uani 1 1 d . . . C1 C 0.0634(3) 0.8597(2) 0.3877(2) 0.0276(5) Uani 1 1 d . . . C2 C 0.0418(3) 0.7381(2) 0.4532(2) 0.0313(5) Uani 1 1 d . . . H2A H 0.1294 0.6790 0.4218 0.038 Uiso 1 1 calc R . . H2B H -0.0938 0.7091 0.4189 0.038 Uiso 1 1 calc R . . C3 C 0.0894(3) 0.7426(2) 0.6156(2) 0.0338(6) Uani 1 1 d . . . H3A H 0.0220 0.8127 0.6474 0.041 Uiso 1 1 calc R . . H3B H 0.0411 0.6677 0.6530 0.041 Uiso 1 1 calc R . . C4 C 0.3042(3) 0.7539(2) 0.6744(2) 0.0322(5) Uani 1 1 d . . . H4A H 0.3867 0.6889 0.6453 0.039 Uiso 1 1 calc R . . C5 C 0.3988(3) 0.8730(2) 0.7072(2) 0.0317(5) Uani 1 1 d . . . H5A H 0.3108 0.9451 0.6849 0.038 Uiso 1 1 calc R . . C6 C 0.6073(3) 0.8945(2) 0.7019(2) 0.0376(6) Uani 1 1 d . . . H6A H 0.6781 0.8161 0.7132 0.045 Uiso 1 1 calc R . . H6B H 0.6693 0.9479 0.7818 0.045 Uiso 1 1 calc R . . C7 C 0.6240(3) 0.9534(2) 0.5616(2) 0.0332(5) Uani 1 1 d . . . H7A H 0.5396 1.0263 0.5450 0.040 Uiso 1 1 calc R . . H7B H 0.7602 0.9803 0.5694 0.040 Uiso 1 1 calc R . . C8 C 0.5668(3) 0.8695(2) 0.4365(2) 0.0313(5) Uani 1 1 d . . . C9 C 0.4607(3) 0.8644(2) 0.1832(2) 0.0343(6) Uani 1 1 d . . . H9A H 0.4270 0.7806 0.2063 0.041 Uiso 1 1 calc R . . H9B H 0.5633 0.8598 0.1280 0.041 Uiso 1 1 calc R . . C10 C 0.2811(3) 0.92775(19) 0.0958(2) 0.0291(5) Uani 1 1 d . . . H10A H 0.2174 0.8698 0.0197 0.035 Uiso 1 1 calc R . . C11 C 0.1319(3) 0.95816(19) 0.1832(2) 0.0278(5) Uani 1 1 d . . . H11A H 0.1873 1.0215 0.2553 0.033 Uiso 1 1 calc R . . C12 C -0.0555(3) 1.0048(2) 0.0906(2) 0.0357(6) Uani 1 1 d . . . H12A H -0.1484 1.0249 0.1505 0.043 Uiso 1 1 calc R . . H12B H -0.1150 0.9408 0.0225 0.043 Uiso 1 1 calc R . . C13 C -0.0173(4) 1.1176(2) 0.0092(2) 0.0397(6) Uani 1 1 d . . . H13A H 0.0239 1.1852 0.0770 0.048 Uiso 1 1 calc R . . H13B H -0.1395 1.1422 -0.0577 0.048 Uiso 1 1 calc R . . C14 C 0.1402(4) 1.0947(2) -0.0737(2) 0.0418(6) Uani 1 1 d . . . H14A H 0.1710 1.1719 -0.1166 0.050 Uiso 1 1 calc R . . H14B H 0.0905 1.0366 -0.1517 0.050 Uiso 1 1 calc R . . C15 C 0.3257(4) 1.0437(2) 0.0219(2) 0.0349(6) Uani 1 1 d . . . H15A H 0.3833 1.1050 0.0942 0.042 Uiso 1 1 calc R . . H15B H 0.4221 1.0257 -0.0360 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0411(9) 0.0252(8) 0.0258(7) -0.0016(6) 0.0105(6) -0.0041(7) O2 0.0592(12) 0.0262(9) 0.0351(8) 0.0000(8) 0.0206(8) 0.0069(8) O3 0.0536(11) 0.0457(10) 0.0244(8) 0.0007(7) 0.0088(7) 0.0006(8) O4 0.0532(11) 0.0297(10) 0.0400(9) 0.0045(7) 0.0125(8) 0.0037(8) O5 0.0408(10) 0.0292(9) 0.0310(8) 0.0024(7) 0.0027(7) -0.0035(7) C1 0.0247(12) 0.0317(13) 0.0272(11) -0.0010(11) 0.0078(9) 0.0028(11) C2 0.0352(14) 0.0271(12) 0.0322(12) 0.0009(10) 0.0087(10) -0.0017(10) C3 0.0436(16) 0.0267(12) 0.0334(12) 0.0038(10) 0.0135(11) -0.0017(11) C4 0.0426(15) 0.0319(13) 0.0226(11) -0.0009(10) 0.0084(10) 0.0026(11) C5 0.0414(15) 0.0318(13) 0.0224(11) 0.0015(10) 0.0082(10) 0.0016(11) C6 0.0414(16) 0.0382(14) 0.0304(12) -0.0001(10) 0.0023(11) -0.0015(11) C7 0.0298(13) 0.0303(13) 0.0379(13) 0.0010(11) 0.0037(10) -0.0019(11) C8 0.0257(13) 0.0326(14) 0.0360(12) 0.0042(12) 0.0077(9) 0.0022(11) C9 0.0386(14) 0.0352(14) 0.0299(11) -0.0021(11) 0.0090(10) 0.0013(12) C10 0.0371(14) 0.0243(12) 0.0265(11) -0.0019(9) 0.0084(10) -0.0036(10) C11 0.0352(14) 0.0233(12) 0.0253(11) 0.0021(10) 0.0073(10) -0.0025(11) C12 0.0364(15) 0.0334(13) 0.0350(13) -0.0029(11) 0.0032(11) 0.0004(11) C13 0.0479(15) 0.0316(14) 0.0366(12) 0.0035(10) 0.0035(11) 0.0093(12) C14 0.0592(17) 0.0333(14) 0.0319(13) 0.0072(10) 0.0080(12) -0.0006(12) C15 0.0460(16) 0.0315(13) 0.0278(12) 0.0015(10) 0.0094(11) -0.0058(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.346(2) . ? O1 C11 1.461(2) . ? O2 C1 1.200(2) . ? O3 C5 1.446(2) . ? O3 C4 1.451(2) . ? O4 C8 1.196(3) . ? O5 C8 1.347(2) . ? O5 C9 1.457(2) . ? C1 C2 1.503(3) . ? C2 C3 1.528(3) . ? C3 C4 1.496(3) . ? C4 C5 1.473(3) . ? C5 C6 1.499(3) . ? C6 C7 1.528(3) . ? C7 C8 1.501(3) . ? C9 C10 1.522(3) . ? C10 C11 1.524(3) . ? C10 C15 1.528(3) . ? C11 C12 1.507(3) . ? C12 C13 1.525(3) . ? C13 C14 1.526(4) . ? C14 C15 1.526(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C11 116.95(16) . . ? C5 O3 C4 61.10(13) . . ? C8 O5 C9 116.96(17) . . ? O2 C1 O1 123.7(2) . . ? O2 C1 C2 125.17(18) . . ? O1 C1 C2 111.08(19) . . ? C1 C2 C3 112.54(18) . . ? C4 C3 C2 111.23(17) . . ? O3 C4 C5 59.29(13) . . ? O3 C4 C3 116.51(17) . . ? C5 C4 C3 121.70(19) . . ? O3 C5 C4 59.62(13) . . ? O3 C5 C6 116.59(18) . . ? C4 C5 C6 122.1(2) . . ? C5 C6 C7 111.55(17) . . ? C8 C7 C6 113.06(19) . . ? O4 C8 O5 123.8(2) . . ? O4 C8 C7 125.56(19) . . ? O5 C8 C7 110.65(19) . . ? O5 C9 C10 109.00(18) . . ? C9 C10 C11 112.56(16) . . ? C9 C10 C15 114.15(19) . . ? C11 C10 C15 108.30(17) . . ? O1 C11 C12 110.55(16) . . ? O1 C11 C10 107.26(16) . . ? C12 C11 C10 111.52(16) . . ? C11 C12 C13 110.54(19) . . ? C12 C13 C14 111.59(19) . . ? C13 C14 C15 111.57(19) . . ? C14 C15 C10 110.6(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.98 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.177 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.046 # Attachment 'uconn_mp08.cif' data_mp08 _database_code_depnum_ccdc_archive 'CCDC 686766' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H22 O5' _chemical_formula_weight 282.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.4153(13) _cell_length_b 12.269(3) _cell_length_c 18.605(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1464.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9859 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3801 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1341 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 28.97 _reflns_number_total 3801 _reflns_number_gt 2021 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(12) _refine_ls_number_reflns 3801 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1525 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _chemical_absolute_configuration syn loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6662(2) 0.46869(12) 0.20280(8) 0.0291(4) Uani 1 1 d . . . O2 O 0.3324(3) 0.41348(13) 0.20603(9) 0.0379(4) Uani 1 1 d . . . O3 O 0.1174(3) 0.40800(14) -0.01143(9) 0.0493(5) Uani 1 1 d . . . O4 O 0.5892(2) 0.63290(14) 0.04353(8) 0.0348(5) Uani 1 1 d . . . O5 O 0.5231(2) 0.69969(12) 0.15381(8) 0.0286(4) Uani 1 1 d . . . C1 C 0.5039(4) 0.40954(19) 0.17933(12) 0.0284(6) Uani 1 1 d . . . C2 C 0.5622(4) 0.33781(19) 0.11692(12) 0.0342(7) Uani 1 1 d . . . H2A H 0.6177 0.2679 0.1353 0.041 Uiso 1 1 calc R . . H2B H 0.6737 0.3736 0.0887 0.041 Uiso 1 1 calc R . . C3 C 0.3754(4) 0.3150(2) 0.06779(13) 0.0376(7) Uani 1 1 d . . . H3A H 0.4097 0.2538 0.0352 0.045 Uiso 1 1 calc R . . H3B H 0.2545 0.2929 0.0975 0.045 Uiso 1 1 calc R . . C4 C 0.3180(4) 0.4130(2) 0.02397(12) 0.0345(6) Uani 1 1 d . . . H4A H 0.4336 0.4454 -0.0051 0.041 Uiso 1 1 calc R . . C5 C 0.1517(4) 0.48842(19) 0.04436(13) 0.0317(6) Uani 1 1 d . . . H5A H 0.0824 0.4734 0.0915 0.038 Uiso 1 1 calc R . . C6 C 0.1475(4) 0.60500(19) 0.01963(12) 0.0302(6) Uani 1 1 d . . . H6A H 0.0017 0.6266 0.0095 0.036 Uiso 1 1 calc R . . H6B H 0.2278 0.6117 -0.0256 0.036 Uiso 1 1 calc R . . C7 C 0.2392(4) 0.6817(2) 0.07568(12) 0.0281(6) Uani 1 1 d . . . H7A H 0.2134 0.7578 0.0604 0.034 Uiso 1 1 calc R . . H7B H 0.1658 0.6702 0.1219 0.034 Uiso 1 1 calc R . . C8 C 0.4664(4) 0.66676(19) 0.08736(12) 0.0247(6) Uani 1 1 d . . . C9 C 0.7416(3) 0.6889(2) 0.17247(12) 0.0305(6) Uani 1 1 d . . . H9A H 0.8108 0.7609 0.1692 0.037 Uiso 1 1 calc R . . H9B H 0.8110 0.6389 0.1383 0.037 Uiso 1 1 calc R . . C10 C 0.7619(4) 0.6447(2) 0.24847(12) 0.0253(6) Uani 1 1 d . . . H10A H 0.7159 0.7034 0.2822 0.030 Uiso 1 1 calc R . . C11 C 0.6238(4) 0.54618(18) 0.26135(11) 0.0281(6) Uani 1 1 d . . . H11A H 0.4746 0.5693 0.2588 0.034 Uiso 1 1 calc R . . C12 C 0.6629(4) 0.4914(2) 0.33332(12) 0.0337(6) Uani 1 1 d . . . H12A H 0.5852 0.4217 0.3350 0.040 Uiso 1 1 calc R . . H12B H 0.6089 0.5386 0.3722 0.040 Uiso 1 1 calc R . . C13 C 0.8934(4) 0.4688(2) 0.34663(13) 0.0361(6) Uani 1 1 d . . . H13A H 0.9117 0.4388 0.3956 0.043 Uiso 1 1 calc R . . H13B H 0.9434 0.4137 0.3118 0.043 Uiso 1 1 calc R . . C14 C 1.0219(4) 0.5719(2) 0.33896(13) 0.0354(6) Uani 1 1 d . . . H14A H 1.1711 0.5549 0.3466 0.042 Uiso 1 1 calc R . . H14B H 0.9787 0.6254 0.3759 0.042 Uiso 1 1 calc R . . C15 C 0.9920(4) 0.6212(2) 0.26401(12) 0.0311(6) Uani 1 1 d . . . H15A H 1.0725 0.6899 0.2605 0.037 Uiso 1 1 calc R . . H15B H 1.0467 0.5701 0.2274 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0266(9) 0.0330(10) 0.0279(9) -0.0053(8) 0.0006(8) 0.0003(8) O2 0.0319(11) 0.0399(11) 0.0419(11) -0.0068(9) 0.0021(9) -0.0056(9) O3 0.0625(13) 0.0377(11) 0.0477(11) -0.0010(10) -0.0273(10) -0.0094(10) O4 0.0293(10) 0.0480(12) 0.0271(9) -0.0013(8) 0.0030(8) 0.0002(8) O5 0.0241(9) 0.0368(11) 0.0249(8) -0.0024(8) -0.0032(8) 0.0028(8) C1 0.0326(15) 0.0221(14) 0.0305(14) 0.0009(12) -0.0051(12) 0.0018(13) C2 0.0426(17) 0.0261(15) 0.0339(14) -0.0019(12) -0.0018(13) 0.0015(12) C3 0.0491(17) 0.0290(15) 0.0345(14) -0.0064(13) -0.0083(14) 0.0014(14) C4 0.0417(16) 0.0332(15) 0.0284(14) -0.0040(12) -0.0064(12) -0.0031(14) C5 0.0315(14) 0.0338(15) 0.0298(14) 0.0005(12) -0.0074(13) -0.0090(13) C6 0.0275(13) 0.0335(16) 0.0296(13) 0.0044(12) -0.0024(11) -0.0007(13) C7 0.0266(13) 0.0315(16) 0.0262(13) 0.0058(12) -0.0019(11) 0.0014(12) C8 0.0302(14) 0.0206(14) 0.0234(13) 0.0056(11) 0.0015(12) -0.0011(12) C9 0.0193(12) 0.0375(16) 0.0347(14) 0.0023(13) -0.0042(11) -0.0021(12) C10 0.0264(13) 0.0254(14) 0.0240(13) -0.0014(11) -0.0025(11) 0.0023(11) C11 0.0297(14) 0.0309(14) 0.0238(13) -0.0074(11) 0.0042(12) 0.0035(12) C12 0.0419(16) 0.0337(15) 0.0256(14) -0.0001(12) 0.0008(12) -0.0024(13) C13 0.0452(16) 0.0384(17) 0.0246(13) 0.0046(12) -0.0018(13) 0.0033(13) C14 0.0316(14) 0.0447(17) 0.0298(14) 0.0027(12) -0.0053(12) 0.0015(13) C15 0.0261(13) 0.0390(16) 0.0281(13) 0.0017(12) -0.0042(12) -0.0008(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.342(3) . ? O1 C11 1.471(3) . ? O2 C1 1.208(3) . ? O3 C4 1.447(3) . ? O3 C5 1.449(3) . ? O4 C8 1.207(3) . ? O5 C8 1.351(3) . ? O5 C9 1.451(3) . ? C1 C2 1.504(3) . ? C2 C3 1.533(3) . ? C3 C4 1.499(3) . ? C4 C5 1.462(3) . ? C5 C6 1.503(3) . ? C6 C7 1.523(3) . ? C7 C8 1.485(3) . ? C9 C10 1.520(3) . ? C10 C11 1.518(3) . ? C10 C15 1.531(3) . ? C11 C12 1.519(3) . ? C12 C13 1.524(3) . ? C13 C14 1.517(3) . ? C14 C15 1.532(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C11 116.56(17) . . ? C4 O3 C5 60.65(14) . . ? C8 O5 C9 116.87(18) . . ? O2 C1 O1 123.4(2) . . ? O2 C1 C2 124.6(2) . . ? O1 C1 C2 112.0(2) . . ? C1 C2 C3 111.9(2) . . ? C4 C3 C2 111.7(2) . . ? O3 C4 C5 59.74(15) . . ? O3 C4 C3 115.6(2) . . ? C5 C4 C3 123.1(2) . . ? O3 C5 C4 59.61(15) . . ? O3 C5 C6 115.22(19) . . ? C4 C5 C6 122.4(2) . . ? C5 C6 C7 111.81(19) . . ? C8 C7 C6 113.8(2) . . ? O4 C8 O5 123.1(2) . . ? O4 C8 C7 125.7(2) . . ? O5 C8 C7 111.2(2) . . ? O5 C9 C10 109.75(18) . . ? C11 C10 C9 112.40(19) . . ? C11 C10 C15 112.5(2) . . ? C9 C10 C15 108.99(19) . . ? O1 C11 C10 106.86(18) . . ? O1 C11 C12 109.63(18) . . ? C10 C11 C12 113.29(19) . . ? C11 C12 C13 112.5(2) . . ? C14 C13 C12 111.1(2) . . ? C13 C14 C15 110.3(2) . . ? C10 C15 C14 111.51(19) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.97 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.205 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.056 # Attachment 'uconn_mp09.cif' data_mp09 _database_code_depnum_ccdc_archive 'CCDC 686767' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 O4' _chemical_formula_weight 226.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8101(16) _cell_length_b 18.266(4) _cell_length_c 9.2291(18) _cell_angle_alpha 90.00 _cell_angle_beta 112.26(3) _cell_angle_gamma 90.00 _cell_volume 1218.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5332 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.1062 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3180 _reflns_number_gt 1530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3180 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1480 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1376 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.03773(18) 0.15726(6) 0.55312(14) 0.0382(4) Uani 1 1 d . . . O2 O 0.04216(18) 0.07137(7) 0.72941(14) 0.0401(4) Uani 1 1 d . . . O3 O 0.6024(2) 0.18041(9) 0.64306(17) 0.0592(5) Uani 1 1 d . . . O4 O 0.38874(19) 0.09745(7) 0.51216(15) 0.0439(4) Uani 1 1 d . . . C1 C 0.0566(3) 0.13449(10) 0.6972(2) 0.0348(5) Uani 1 1 d . . . C2 C 0.0970(3) 0.19672(10) 0.8115(2) 0.0406(5) Uani 1 1 d . . . H2A H -0.0168 0.2096 0.8291 0.049 Uiso 1 1 calc R . . H2B H 0.1356 0.2401 0.7673 0.049 Uiso 1 1 calc R . . C3 C 0.2504(3) 0.17623(11) 0.9682(2) 0.0440(5) Uani 1 1 d . . . H3A H 0.2647 0.2160 1.0447 0.053 Uiso 1 1 calc R . . H3B H 0.2143 0.1312 1.0093 0.053 Uiso 1 1 calc R . . C4 C 0.4318(3) 0.16368(11) 0.9514(2) 0.0413(5) Uani 1 1 d . . . H4A H 0.5019 0.2055 0.9470 0.050 Uiso 1 1 calc R . . C5 C 0.5006(3) 0.09942(11) 0.9425(2) 0.0397(5) Uani 1 1 d . . . H5A H 0.4349 0.0579 0.9560 0.048 Uiso 1 1 calc R . . C6 C 0.6735(3) 0.08510(11) 0.9130(2) 0.0451(5) Uani 1 1 d . . . H6A H 0.7484 0.0475 0.9872 0.054 Uiso 1 1 calc R . . H6B H 0.7478 0.1306 0.9314 0.054 Uiso 1 1 calc R . . C7 C 0.6286(3) 0.05884(12) 0.7452(2) 0.0450(5) Uani 1 1 d . . . H7A H 0.7435 0.0423 0.7337 0.054 Uiso 1 1 calc R . . H7B H 0.5426 0.0167 0.7226 0.054 Uiso 1 1 calc R . . C8 C 0.5423(3) 0.11909(12) 0.6312(2) 0.0428(5) Uani 1 1 d . . . C9 C 0.2870(3) 0.15369(12) 0.4027(2) 0.0484(6) Uani 1 1 d . . . H9A H 0.3438 0.1626 0.3249 0.058 Uiso 1 1 calc R . . H9B H 0.2894 0.2000 0.4590 0.058 Uiso 1 1 calc R . . C10 C 0.0902(3) 0.12745(11) 0.3216(2) 0.0444(5) Uani 1 1 d . . . H10A H 0.0882 0.0873 0.2490 0.053 Uiso 1 1 calc R . . H10B H 0.0145 0.1681 0.2583 0.053 Uiso 1 1 calc R . . C11 C 0.0026(3) 0.10048(10) 0.4329(2) 0.0371(5) Uani 1 1 d . . . H11A H 0.0654 0.0542 0.4837 0.045 Uiso 1 1 calc R . . C12 C -0.2028(3) 0.08668(11) 0.3558(2) 0.0455(5) Uani 1 1 d . . . H12A H -0.2498 0.0697 0.4344 0.068 Uiso 1 1 calc R . . H12B H -0.2261 0.0493 0.2744 0.068 Uiso 1 1 calc R . . H12C H -0.2658 0.1322 0.3084 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0462(9) 0.0276(7) 0.0364(7) -0.0016(6) 0.0107(6) 0.0004(6) O2 0.0436(9) 0.0306(8) 0.0465(8) 0.0016(6) 0.0176(6) -0.0025(6) O3 0.0538(10) 0.0557(10) 0.0618(10) 0.0035(8) 0.0148(8) -0.0214(8) O4 0.0423(9) 0.0427(8) 0.0440(8) -0.0028(6) 0.0135(7) -0.0052(7) C1 0.0281(11) 0.0336(12) 0.0400(11) -0.0001(9) 0.0099(8) 0.0026(9) C2 0.0432(13) 0.0340(11) 0.0446(11) -0.0032(9) 0.0165(10) 0.0026(10) C3 0.0528(14) 0.0396(12) 0.0374(11) -0.0059(9) 0.0145(10) 0.0003(10) C4 0.0405(13) 0.0391(12) 0.0390(11) -0.0059(9) 0.0091(9) -0.0059(10) C5 0.0388(12) 0.0349(11) 0.0414(11) 0.0043(9) 0.0109(9) 0.0000(10) C6 0.0374(12) 0.0413(12) 0.0506(13) 0.0019(10) 0.0098(10) -0.0022(10) C7 0.0337(12) 0.0458(13) 0.0547(12) -0.0025(10) 0.0158(10) -0.0031(10) C8 0.0379(12) 0.0481(14) 0.0456(11) -0.0060(10) 0.0193(10) -0.0122(11) C9 0.0557(15) 0.0477(13) 0.0417(11) 0.0062(10) 0.0184(10) -0.0052(11) C10 0.0492(14) 0.0417(12) 0.0362(10) 0.0019(9) 0.0092(9) -0.0022(10) C11 0.0422(12) 0.0291(10) 0.0351(10) -0.0033(8) 0.0090(9) -0.0005(9) C12 0.0410(12) 0.0413(12) 0.0453(11) -0.0022(9) 0.0062(9) 0.0053(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.347(2) . ? O1 C11 1.467(2) . ? O2 C1 1.207(2) . ? O3 C8 1.204(2) . ? O4 C8 1.343(2) . ? O4 C9 1.449(2) . ? C1 C2 1.501(3) . ? C2 C3 1.534(3) . ? C3 C4 1.500(3) . ? C4 C5 1.306(3) . ? C5 C6 1.499(3) . ? C6 C7 1.529(3) . ? C7 C8 1.495(3) . ? C9 C10 1.511(3) . ? C10 C11 1.516(3) . ? C11 C12 1.509(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C11 116.58(14) . . ? C8 O4 C9 116.46(15) . . ? O2 C1 O1 123.56(16) . . ? O2 C1 C2 124.40(17) . . ? O1 C1 C2 112.04(16) . . ? C1 C2 C3 111.01(16) . . ? C4 C3 C2 111.79(17) . . ? C5 C4 C3 124.80(19) . . ? C4 C5 C6 126.05(19) . . ? C5 C6 C7 111.21(17) . . ? C8 C7 C6 110.56(17) . . ? O3 C8 O4 123.05(19) . . ? O3 C8 C7 124.37(19) . . ? O4 C8 C7 112.58(17) . . ? O4 C9 C10 107.86(16) . . ? C9 C10 C11 113.78(16) . . ? O1 C11 C12 109.61(16) . . ? O1 C11 C10 106.23(15) . . ? C12 C11 C10 113.98(16) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.204 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.050