data_mp1 _vrf_STRVA01_mp1 ; PROBLEM: Flack test results are meaningless. RESPONSE:Crystal structure collected only contains light atoms - C, H and O. The absolute configuration cannot be verified by crystallography as the standard deviation on the Flack parameter is too high. The stereo chemistry has been assigned from chemical synthetic knowledge. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 O4' _chemical_formula_sum 'C14 H20 O4' _chemical_formula_weight 252.30 _chemical_absolute_configuration syn 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 'C2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 21.972(4) _cell_length_b 5.2014(10) _cell_length_c 12.991(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.393(3) _cell_angle_gamma 90.00 _cell_volume 1318.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2700 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9658 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details 'sadabs 2008/2' _exptl_special_details ; Collected, solved and refined by Dr. Zoe R. Turner (Princeton) ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3982 _diffrn_reflns_av_R_equivalents 0.0096 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2760 _reflns_number_gt 2701 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _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^ > 2\s(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^)+(0.0367P)^2^+0.5117P] 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, 1081 Friedel Pairs' _refine_ls_abs_structure_Flack 0.0(6) _refine_ls_number_reflns 2760 _refine_ls_number_parameters 166 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.47035(7) 0.2991(3) 1.31434(10) 0.0243(2) Uani 1 1 d . . . H1A H 0.4548 0.1282 1.2807 0.036 Uiso 1 1 calc R . . H1B H 0.4772 0.3009 1.3944 0.036 Uiso 1 1 calc R . . H1C H 0.5137 0.3401 1.3135 0.036 Uiso 1 1 calc R . . C2 C 0.41625(6) 0.4993(2) 1.24303(9) 0.0194(2) Uani 1 1 d . . . H2A H 0.3752 0.4747 1.2549 0.023 Uiso 1 1 calc R . . H2B H 0.4346 0.6733 1.2712 0.023 Uiso 1 1 calc R . . C3 C 0.39519(5) 0.4821(2) 1.11397(9) 0.0155(2) Uani 1 1 d . . . H3 H 0.3731 0.3108 1.0857 0.019 Uiso 1 1 calc R . . C4 C 0.34543(5) 0.6883(2) 1.03817(9) 0.0150(2) Uani 1 1 d . . . H4 H 0.3607 0.8606 1.0754 0.018 Uiso 1 1 calc R . . C5 C 0.35251(5) 0.6765(2) 0.92592(9) 0.0152(2) Uani 1 1 d . . . H5 H 0.3150 0.5662 0.8683 0.018 Uiso 1 1 calc R . . C6 C 0.35009(6) 0.9351(2) 0.87216(9) 0.0181(2) Uani 1 1 d . . . H6A H 0.3064 1.0230 0.8543 0.022 Uiso 1 1 calc R . . H6B H 0.3884 1.0442 0.9264 0.022 Uiso 1 1 calc R . . C7 C 0.35338(7) 1.1297(2) 0.71055(10) 0.0245(3) Uani 1 1 d . . . H7A H 0.3944 1.2344 0.7585 0.029 Uiso 1 1 calc R . . H7B H 0.3122 1.2290 0.6986 0.029 Uiso 1 1 calc R . . C8 C 0.35116(6) 1.0715(2) 0.59494(9) 0.0184(2) Uani 1 1 d . . . C9 C 0.38756(7) 0.8673(3) 0.58124(10) 0.0247(3) Uani 1 1 d . . . H9 H 0.4145 0.7600 0.6454 0.030 Uiso 1 1 calc R . . C10 C 0.38459(7) 0.8197(3) 0.47331(11) 0.0280(3) Uani 1 1 d . . . H10 H 0.4096 0.6801 0.4643 0.034 Uiso 1 1 calc R . . C11 C 0.34529(6) 0.9751(3) 0.37909(10) 0.0258(3) Uani 1 1 d . . . H11 H 0.3430 0.9411 0.3055 0.031 Uiso 1 1 calc R . . C12 C 0.30951(6) 1.1794(3) 0.39280(10) 0.0282(3) Uani 1 1 d . . . H12 H 0.2830 1.2877 0.3288 0.034 Uiso 1 1 calc R . . C13 C 0.31216(6) 1.2272(3) 0.50058(10) 0.0242(2) Uani 1 1 d . . . H13 H 0.2871 1.3670 0.5094 0.029 Uiso 1 1 calc R . . C14 C 0.45285(5) 0.5110(2) 1.08000(9) 0.0168(2) Uani 1 1 d . . . H14 H 0.4812 0.3510 1.0987 0.020 Uiso 1 1 calc R . . O1 O 0.27716(4) 0.63873(17) 1.01940(7) 0.02073(18) Uani 1 1 d . . . H1 H 0.2556 0.7781 1.0074 0.031 Uiso 1 1 calc R . . O2 O 0.49312(4) 0.72237(18) 1.13828(7) 0.02156(18) Uani 1 1 d . . . H2 H 0.5280 0.7272 1.1276 0.032 Uiso 1 1 calc R . . O3 O 0.41769(4) 0.55386(16) 0.95673(6) 0.01799(17) Uani 1 1 d . . . O4 O 0.35572(4) 0.89396(16) 0.76853(7) 0.01977(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0270(6) 0.0229(6) 0.0217(5) 0.0035(4) 0.0101(5) 0.0007(5) C2 0.0227(5) 0.0196(6) 0.0199(5) -0.0006(4) 0.0133(4) -0.0008(5) C3 0.0150(5) 0.0150(5) 0.0182(5) -0.0016(4) 0.0091(4) -0.0015(4) C4 0.0129(4) 0.0142(5) 0.0206(5) -0.0008(4) 0.0098(4) -0.0014(4) C5 0.0119(4) 0.0156(5) 0.0187(4) -0.0014(4) 0.0075(4) 0.0002(4) C6 0.0209(5) 0.0167(6) 0.0196(5) -0.0011(4) 0.0118(4) 0.0008(4) C7 0.0363(6) 0.0166(6) 0.0250(5) 0.0005(4) 0.0177(5) -0.0002(5) C8 0.0178(5) 0.0174(6) 0.0206(5) -0.0005(4) 0.0093(4) -0.0034(4) C9 0.0308(6) 0.0220(6) 0.0209(5) 0.0035(5) 0.0115(5) 0.0068(5) C10 0.0360(7) 0.0252(7) 0.0261(6) 0.0017(5) 0.0170(5) 0.0079(5) C11 0.0289(6) 0.0301(7) 0.0195(5) -0.0006(5) 0.0120(5) -0.0014(5) C12 0.0248(6) 0.0343(8) 0.0217(5) 0.0077(5) 0.0074(5) 0.0052(6) C13 0.0217(5) 0.0245(6) 0.0277(6) 0.0040(5) 0.0124(4) 0.0057(5) C14 0.0143(4) 0.0196(6) 0.0167(5) -0.0005(4) 0.0073(4) 0.0002(4) O1 0.0142(3) 0.0184(4) 0.0335(4) 0.0016(3) 0.0144(3) 0.0006(3) O2 0.0151(4) 0.0276(5) 0.0230(4) -0.0042(3) 0.0097(3) -0.0058(3) O3 0.0146(3) 0.0237(4) 0.0167(3) -0.0002(3) 0.0081(3) 0.0035(3) O4 0.0255(4) 0.0168(4) 0.0204(4) 0.0002(3) 0.0135(3) 0.0004(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5304(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.5229(14) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C14 1.5285(14) . ? C3 C4 1.5247(15) . ? C3 H3 1.0000 . ? C4 O1 1.4280(12) . ? C4 C5 1.5372(14) . ? C4 H4 1.0000 . ? C5 O3 1.4460(12) . ? C5 C6 1.5054(16) . ? C5 H5 1.0000 . ? C6 O4 1.4236(12) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O4 1.4276(14) . ? C7 C8 1.5108(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.3895(18) . ? C8 C13 1.3876(16) . ? C9 C10 1.3954(16) . ? C9 H9 0.9500 . ? C10 C11 1.3872(18) . ? C10 H10 0.9500 . ? C11 C12 1.381(2) . ? C11 H11 0.9500 . ? C12 C13 1.3967(17) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O2 1.3960(14) . ? C14 O3 1.4396(12) . ? C14 H14 1.0000 . ? O1 H1 0.8400 . ? O2 H2 0.8400 . ? 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 C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C1 112.61(9) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C14 C3 C2 116.09(9) . . ? C14 C3 C4 100.83(8) . . ? C2 C3 C4 115.73(9) . . ? C14 C3 H3 107.9 . . ? C2 C3 H3 107.9 . . ? C4 C3 H3 107.9 . . ? O1 C4 C3 111.60(9) . . ? O1 C4 C5 112.81(8) . . ? C3 C4 C5 103.24(8) . . ? O1 C4 H4 109.7 . . ? C3 C4 H4 109.7 . . ? C5 C4 H4 109.7 . . ? O3 C5 C6 109.97(8) . . ? O3 C5 C4 105.95(8) . . ? C6 C5 C4 114.02(9) . . ? O3 C5 H5 108.9 . . ? C6 C5 H5 108.9 . . ? C4 C5 H5 108.9 . . ? O4 C6 C5 107.73(9) . . ? O4 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? O4 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? O4 C7 C8 109.23(10) . . ? O4 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? O4 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C13 119.40(11) . . ? C9 C8 C7 121.55(11) . . ? C13 C8 C7 119.06(11) . . ? C8 C9 C10 120.04(11) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.38(12) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.64(11) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.16(11) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C8 C13 C12 120.38(12) . . ? C8 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? O2 C14 O3 111.28(9) . . ? O2 C14 C3 108.87(9) . . ? O3 C14 C3 104.16(8) . . ? O2 C14 H14 110.8 . . ? O3 C14 H14 110.8 . . ? C3 C14 H14 110.8 . . ? C4 O1 H1 109.5 . . ? C14 O2 H2 109.5 . . ? C14 O3 C5 109.42(8) . . ? C6 O4 C7 111.85(9) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.257 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.031