# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global_1 data_filip-inv #TrackingRef '9742_web_deposit_cif_file_0_RadomirN.Saicic_1329912564.filip-inv sa autorima ACIE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H18 O4' _chemical_formula_sum 'C11 H18 O4' _chemical_formula_weight 214.25 _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_space_group_name_H-M 'P 1 21 1' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8534(5) _cell_length_b 9.4451(5) _cell_length_c 9.3061(6) _cell_angle_alpha 90.0 _cell_angle_beta 94.800(6) _cell_angle_gamma 90.0 _cell_volume 600.28(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1298 _cell_measurement_theta_min 3.0755 _cell_measurement_theta_max 28.7001 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_min 0.94944 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.3280 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3170 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1751 _reflns_number_gt 1211 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics MERCURY _computing_publication_material WINGX _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^)+(0.0260P)^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 SHELXL _refine_ls_extinction_coef 0.020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 1751 _refine_ls_number_parameters 141 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0540 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _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 0.06631(18) 0.49565(14) 0.07249(14) 0.0583(4) Uani 1 1 d . . . O2 O 0.2506(2) 0.35692(15) 0.21922(15) 0.0744(5) Uani 1 1 d . . . O3 O 0.3318(2) 0.89432(14) 0.30881(17) 0.0848(5) Uani 1 1 d . . . H3 H 0.3666 0.9703 0.3450 0.127 Uiso 1 1 calc R . . O4 O 0.5552(2) 0.66616(14) 0.59177(16) 0.0685(5) Uani 1 1 d . . . H4 H 0.6217 0.7093 0.6547 0.103 Uiso 1 1 calc R . . C1 C 0.0402(3) 0.3806(3) -0.0282(2) 0.0743(7) Uani 1 1 d . . . H1A H 0.1619 0.3615 -0.0686 0.111 Uiso 1 1 calc R . . H1B H -0.0574 0.4057 -0.1040 0.111 Uiso 1 1 calc R . . H1C H -0.0012 0.2977 0.0207 0.111 Uiso 1 1 calc R . . C2 C 0.1794(3) 0.4705(2) 0.1919(2) 0.0474(5) Uani 1 1 d . . . C3 C 0.2089(3) 0.59972(17) 0.2844(2) 0.0465(5) Uani 1 1 d . . . H3A H 0.1185 0.6737 0.2463 0.056 Uiso 1 1 calc R . . C4 C 0.1690(3) 0.5687(2) 0.4404(2) 0.0569(6) Uani 1 1 d . . . H4A H 0.0342 0.5385 0.4434 0.068 Uiso 1 1 calc R . . H4B H 0.2529 0.4918 0.4770 0.068 Uiso 1 1 calc R . . C5 C 0.2056(3) 0.6976(2) 0.5365(2) 0.0665(6) Uani 1 1 d . . . H5 H 0.1108 0.7702 0.5019 0.080 Uiso 1 1 calc R . . C6 C 0.1678(4) 0.6643(4) 0.6930(3) 0.1103(10) Uani 1 1 d . . . H6A H 0.0367 0.6294 0.6963 0.165 Uiso 1 1 calc R . . H6B H 0.1841 0.7488 0.7500 0.165 Uiso 1 1 calc R . . H6C H 0.2591 0.5938 0.7308 0.165 Uiso 1 1 calc R . . C7 C 0.4091(3) 0.7590(2) 0.5248(2) 0.0619(7) Uani 1 1 d . . . H7 H 0.4172 0.8498 0.5760 0.074 Uiso 1 1 calc R . . C8 C 0.4528(3) 0.78465(19) 0.3704(2) 0.0588(6) Uani 1 1 d . . . H8 H 0.5900 0.8137 0.3694 0.071 Uiso 1 1 calc R . . C9 C 0.4201(3) 0.6526(2) 0.2778(2) 0.0500(5) Uani 1 1 d . . . H9 H 0.5072 0.5788 0.3206 0.060 Uiso 1 1 calc R . . C10 C 0.4721(4) 0.6748(3) 0.1261(3) 0.0719(7) Uani 1 1 d . . . H10 H 0.4194 0.7537 0.0773 0.086 Uiso 1 1 calc R . . C11 C 0.5847(4) 0.5930(4) 0.0573(3) 0.1020(10) Uani 1 1 d . . . H11A H 0.6403 0.5130 0.1023 0.122 Uiso 1 1 calc R . . H11B H 0.6097 0.6144 -0.0369 0.122 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 0.0646(9) 0.0501(9) 0.0551(10) -0.0045(8) -0.0243(8) 0.0034(7) O2 0.1032(11) 0.0390(10) 0.0732(11) -0.0044(8) -0.0392(9) 0.0118(8) O3 0.1202(13) 0.0312(8) 0.0929(12) 0.0063(9) -0.0520(9) -0.0014(9) O4 0.0899(12) 0.0394(8) 0.0686(11) -0.0056(7) -0.0386(8) 0.0076(9) C1 0.0956(17) 0.0644(16) 0.0574(15) -0.0190(13) -0.0252(13) -0.0023(14) C2 0.0495(11) 0.0389(12) 0.0507(13) 0.0004(11) -0.0138(10) -0.0020(12) C3 0.0537(13) 0.0328(13) 0.0496(13) 0.0001(10) -0.0156(10) 0.0016(10) C4 0.0556(13) 0.0517(13) 0.0621(15) -0.0012(12) -0.0031(10) 0.0005(11) C5 0.0726(16) 0.0600(16) 0.0650(16) -0.0138(12) -0.0054(12) 0.0161(12) C6 0.133(2) 0.134(2) 0.0652(19) -0.0234(18) 0.0156(16) 0.007(2) C7 0.0824(17) 0.0328(11) 0.0645(16) -0.0112(12) -0.0290(13) 0.0111(11) C8 0.0709(16) 0.0347(13) 0.0655(16) 0.0041(12) -0.0255(11) -0.0080(11) C9 0.0544(13) 0.0390(11) 0.0542(14) 0.0028(11) -0.0096(10) -0.0072(10) C10 0.0829(17) 0.0632(17) 0.0683(18) 0.0115(15) -0.0020(13) -0.0129(14) C11 0.110(2) 0.114(2) 0.085(2) 0.002(2) 0.0274(18) -0.0103(19) _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 C2 1.322(2) . ? O1 C1 1.436(2) . ? O2 C2 1.197(2) . ? O3 C8 1.418(2) . ? O3 H3 0.8200 . ? O4 C7 1.434(2) . ? O4 H4 0.8200 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.497(3) . ? C3 C4 1.528(3) . ? C3 C9 1.537(3) . ? C3 H3A 0.9800 . ? C4 C5 1.518(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C7 1.522(3) . ? C5 C6 1.533(3) . ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.512(3) . ? C7 H7 0.9800 . ? C8 C9 1.522(3) . ? C8 H8 0.9800 . ? C9 C10 1.500(3) . ? C9 H9 0.9800 . ? C10 C11 1.298(3) . ? C10 H10 0.9300 . ? C11 H11A 0.9300 . ? C11 H11B 0.9300 . ? 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 O1 C1 116.40(19) . . ? C8 O3 H3 109.5 . . ? C7 O4 H4 109.5 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 122.63(19) . . ? O2 C2 C3 125.15(16) . . ? O1 C2 C3 112.22(18) . . ? C2 C3 C4 111.33(16) . . ? C2 C3 C9 108.90(17) . . ? C4 C3 C9 110.09(14) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C9 C3 H3A 108.8 . . ? C5 C4 C3 111.84(17) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 C7 111.75(18) . . ? C4 C5 C6 111.3(2) . . ? C7 C5 C6 111.97(19) . . ? C4 C5 H5 107.2 . . ? C7 C5 H5 107.2 . . ? C6 C5 H5 107.2 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 C8 108.91(19) . . ? O4 C7 C5 110.27(18) . . ? C8 C7 C5 112.61(16) . . ? O4 C7 H7 108.3 . . ? C8 C7 H7 108.3 . . ? C5 C7 H7 108.3 . . ? O3 C8 C7 110.21(18) . . ? O3 C8 C9 108.44(15) . . ? C7 C8 C9 112.04(17) . . ? O3 C8 H8 108.7 . . ? C7 C8 H8 108.7 . . ? C9 C8 H8 108.7 . . ? C10 C9 C8 112.50(19) . . ? C10 C9 C3 112.44(16) . . ? C8 C9 C3 109.77(17) . . ? C10 C9 H9 107.3 . . ? C8 C9 H9 107.3 . . ? C3 C9 H9 107.3 . . ? C11 C10 C9 125.4(2) . . ? C11 C10 H10 117.3 . . ? C9 C10 H10 117.3 . . ? C10 C11 H11A 120.0 . . ? C10 C11 H11B 120.0 . . ? H11A C11 H11B 120.0 . . ? 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 C1 O1 C2 O2 -3.1(3) . . . . ? C1 O1 C2 C3 175.84(17) . . . . ? O2 C2 C3 C4 -50.9(3) . . . . ? O1 C2 C3 C4 130.21(17) . . . . ? O2 C2 C3 C9 70.7(3) . . . . ? O1 C2 C3 C9 -108.22(17) . . . . ? C2 C3 C4 C5 177.91(16) . . . . ? C9 C3 C4 C5 57.0(2) . . . . ? C3 C4 C5 C7 -53.2(2) . . . . ? C3 C4 C5 C6 -179.20(17) . . . . ? C4 C5 C7 O4 -70.7(2) . . . . ? C6 C5 C7 O4 54.9(2) . . . . ? C4 C5 C7 C8 51.2(2) . . . . ? C6 C5 C7 C8 176.7(2) . . . . ? O4 C7 C8 O3 -170.03(14) . . . . ? C5 C7 C8 O3 67.3(2) . . . . ? O4 C7 C8 C9 69.1(2) . . . . ? C5 C7 C8 C9 -53.5(2) . . . . ? O3 C8 C9 C10 60.8(2) . . . . ? C7 C8 C9 C10 -177.30(18) . . . . ? O3 C8 C9 C3 -65.2(2) . . . . ? C7 C8 C9 C3 56.7(2) . . . . ? C2 C3 C9 C10 53.6(2) . . . . ? C4 C3 C9 C10 175.89(18) . . . . ? C2 C3 C9 C8 179.62(15) . . . . ? C4 C3 C9 C8 -58.1(2) . . . . ? C8 C9 C10 C11 129.6(3) . . . . ? C3 C9 C10 C11 -105.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O4 0.82 2.00 2.816(2) 172.7 2_656 O4 H4 O2 0.82 1.98 2.778(2) 164.9 2_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.087 _refine_diff_density_min -0.095 _refine_diff_density_rms 0.020 _database_code_depnum_ccdc_archive 'CCDC 868561'