data_mp3 _vrf_STRVA01_mp3 ; 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. ; #End validation reply _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 O4' _chemical_formula_sum 'C14 H18 O4' _chemical_formula_weight 250.28 _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 'Orthorhombic' _symmetry_space_group_name_H-M 'P2(1)2(1)2(1)' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.0402(13) _cell_length_b 8.8190(16) _cell_length_c 20.478(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1271.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2187 _cell_measurement_theta_min 6.64 _cell_measurement_theta_max 27.54 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9469 _exptl_absorpt_correction_T_max 0.9849 _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 'phi and 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 6915 _diffrn_reflns_av_R_equivalents 0.0111 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.55 _reflns_number_total 2905 _reflns_number_gt 2881 _reflns_threshold_expression >2\s(I) _computing_data_collection 'BRUKER, APEX II SOFTWARE SUITE' _computing_cell_refinement 'BRUKER, APEX II SOFTWARE SUITE' _computing_data_reduction 'BRUKER, APEX II SOFTWARE SUITE' _computing_structure_solution 'SIR-92 (Giacovazzo, 1994)' _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^)+(0.0430P)^2^+0.2409P] 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., 1197 Friedel pairs' _refine_ls_abs_structure_Flack 0.2(6) _refine_ls_number_reflns 2905 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0684 _refine_ls_wR_factor_gt 0.0683 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.25206(15) 0.64764(11) 0.66791(5) 0.01792(19) Uani 1 1 d . . . H1A H 0.3504 0.6461 0.6340 0.027 Uiso 1 1 calc R . . H1B H 0.2821 0.7263 0.7001 0.027 Uiso 1 1 calc R . . H1C H 0.1286 0.6695 0.6479 0.027 Uiso 1 1 calc R . . C2 C 0.24441(13) 0.49200(10) 0.70202(4) 0.01329(18) Uani 1 1 d . . . C3 C 0.09899(13) 0.49039(11) 0.75842(4) 0.01360(18) Uani 1 1 d . . . H3 H 0.0658 0.3836 0.7703 0.016 Uiso 1 1 calc R . . C4 C 0.21021(13) 0.56508(11) 0.81382(4) 0.01401(18) Uani 1 1 d . . . H4 H 0.2015 0.6776 0.8088 0.017 Uiso 1 1 calc R . . C5 C 0.15042(14) 0.52354(11) 0.88220(5) 0.01566(19) Uani 1 1 d . . . H5A H 0.2330 0.5760 0.9142 0.019 Uiso 1 1 calc R . . H5B H 0.0179 0.5567 0.8898 0.019 Uiso 1 1 calc R . . C6 C 0.09906(15) 0.32324(11) 0.95438(4) 0.01579(18) Uani 1 1 d . . . H6A H -0.0393 0.3418 0.9576 0.019 Uiso 1 1 calc R . . H6B H 0.1633 0.3865 0.9876 0.019 Uiso 1 1 calc R . . C7 C 0.14000(13) 0.15791(11) 0.96743(5) 0.01350(18) Uani 1 1 d . . . C8 C 0.23658(14) 0.06791(11) 0.92264(4) 0.01493(19) Uani 1 1 d . . . H8 H 0.2724 0.1085 0.8815 0.018 Uiso 1 1 calc R . . C9 C 0.28088(15) -0.08242(12) 0.93824(5) 0.01728(19) Uani 1 1 d . . . H9 H 0.3464 -0.1438 0.9075 0.021 Uiso 1 1 calc R . . C10 C 0.22972(15) -0.14253(11) 0.99845(5) 0.0181(2) Uani 1 1 d . . . H10 H 0.2622 -0.2441 1.0092 0.022 Uiso 1 1 calc R . . C11 C 0.13064(14) -0.05311(12) 1.04293(5) 0.01714(19) Uani 1 1 d . . . H11 H 0.0942 -0.0941 1.0840 0.021 Uiso 1 1 calc R . . C12 C 0.08482(14) 0.09611(11) 1.02742(5) 0.01527(18) Uani 1 1 d . . . H12 H 0.0158 0.1563 1.0577 0.018 Uiso 1 1 calc R . . C13 C 0.21601(15) 0.36570(11) 0.65233(5) 0.0184(2) Uani 1 1 d . . . H13A H 0.2185 0.2674 0.6746 0.028 Uiso 1 1 calc R . . H13B H 0.3181 0.3694 0.6198 0.028 Uiso 1 1 calc R . . H13C H 0.0932 0.3789 0.6305 0.028 Uiso 1 1 calc R . . C14 C 0.42836(14) 0.47427(10) 0.73997(4) 0.01395(18) Uani 1 1 d . . . O1 O -0.06795(10) 0.57502(8) 0.74642(4) 0.01848(15) Uani 1 1 d . . . H1 H -0.1577 0.5156 0.7377 0.028 Uiso 1 1 calc R . . O2 O 0.58030(10) 0.43127(9) 0.71985(3) 0.01867(15) Uani 1 1 d . . . O3 O 0.40659(10) 0.51864(8) 0.80264(3) 0.01584(15) Uani 1 1 d . . . O4 O 0.16413(10) 0.36444(8) 0.89118(3) 0.01534(15) 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 0.0189(4) 0.0172(4) 0.0177(4) 0.0045(4) -0.0018(4) -0.0012(4) C2 0.0121(4) 0.0150(4) 0.0127(4) 0.0001(3) -0.0007(3) -0.0004(4) C3 0.0116(4) 0.0147(4) 0.0144(4) 0.0005(3) -0.0005(3) 0.0003(4) C4 0.0125(4) 0.0147(4) 0.0148(4) -0.0003(3) -0.0006(3) 0.0007(3) C5 0.0184(4) 0.0144(4) 0.0142(4) -0.0006(3) 0.0010(3) 0.0016(3) C6 0.0159(4) 0.0185(4) 0.0131(4) 0.0014(3) 0.0032(3) 0.0024(4) C7 0.0101(4) 0.0165(4) 0.0139(4) -0.0001(3) -0.0016(3) -0.0008(3) C8 0.0141(4) 0.0186(4) 0.0121(4) 0.0001(3) 0.0004(3) -0.0012(4) C9 0.0170(4) 0.0183(4) 0.0165(4) -0.0030(4) 0.0011(4) 0.0012(4) C10 0.0190(4) 0.0161(4) 0.0191(4) 0.0009(3) -0.0005(4) 0.0000(4) C11 0.0164(4) 0.0208(5) 0.0142(4) 0.0021(4) 0.0004(3) -0.0023(4) C12 0.0120(4) 0.0201(4) 0.0137(4) -0.0007(3) 0.0010(4) -0.0003(3) C13 0.0186(4) 0.0201(4) 0.0166(4) -0.0045(4) -0.0002(4) -0.0025(4) C14 0.0138(4) 0.0130(4) 0.0150(4) 0.0024(3) -0.0009(3) -0.0021(3) O1 0.0115(3) 0.0200(3) 0.0239(3) -0.0003(3) -0.0024(3) 0.0021(3) O2 0.0131(3) 0.0240(3) 0.0189(3) 0.0013(3) 0.0017(3) 0.0010(3) O3 0.0121(3) 0.0211(3) 0.0143(3) 0.0002(3) -0.0011(2) -0.0006(3) O4 0.0196(3) 0.0142(3) 0.0122(3) 0.0006(2) 0.0021(3) 0.0008(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 1.5411(13) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C14 1.5183(13) . ? C2 C13 1.5218(13) . ? C2 C3 1.5434(13) . ? C3 O1 1.4138(11) . ? C3 C4 1.5277(13) . ? C3 H3 1.0000 . ? C4 O3 1.4600(11) . ? C4 C5 1.5074(13) . ? C4 H4 1.0000 . ? C5 O4 1.4183(12) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O4 1.4203(11) . ? C6 C7 1.5101(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.3905(13) . ? C7 C12 1.3990(13) . ? C8 C9 1.3989(14) . ? C8 H8 0.9500 . ? C9 C10 1.3895(14) . ? C9 H9 0.9500 . ? C10 C11 1.3922(14) . ? C10 H10 0.9500 . ? C11 C12 1.3917(14) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O2 1.2074(12) . ? C14 O3 1.3505(12) . ? O1 H1 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 . . ? C14 C2 C13 112.27(8) . . ? C14 C2 C1 107.09(7) . . ? C13 C2 C1 110.69(8) . . ? C14 C2 C3 100.48(7) . . ? C13 C2 C3 113.98(8) . . ? C1 C2 C3 111.75(8) . . ? O1 C3 C4 109.12(8) . . ? O1 C3 C2 114.61(8) . . ? C4 C3 C2 102.22(7) . . ? O1 C3 H3 110.2 . . ? C4 C3 H3 110.2 . . ? C2 C3 H3 110.2 . . ? O3 C4 C5 109.99(7) . . ? O3 C4 C3 104.36(7) . . ? C5 C4 C3 116.23(8) . . ? O3 C4 H4 108.7 . . ? C5 C4 H4 108.7 . . ? C3 C4 H4 108.7 . . ? O4 C5 C4 109.99(8) . . ? O4 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? O4 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? O4 C6 C7 110.29(8) . . ? O4 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? O4 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C12 119.52(9) . . ? C8 C7 C6 121.86(9) . . ? C12 C7 C6 118.59(8) . . ? C9 C8 C7 119.95(9) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.43(9) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 119.63(9) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 120.16(9) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C7 120.29(9) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 O3 121.05(9) . . ? O2 C14 C2 127.83(8) . . ? O3 C14 C2 111.08(8) . . ? C3 O1 H1 109.5 . . ? C14 O3 C4 109.74(7) . . ? C5 O4 C6 110.45(7) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.237 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.041