Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Boyd, Derek R.' 'Sharma, Narain D.' 'Loke, Pui L.' 'Malone, John F.' 'McRoberts, W. Colin' 'Hamilton, John T.G.' _publ_requested journal 'Chemical Communications' _publ_contact_author_name 'Prof Derek R. Boyd' _publ_contact_author_address ; Queen's University of Belfast Queen's University of Belfast Belfast, BT9 5AG BT9 5AG UNITED KINGDOM ; _publ_contact_author_email 'DR.BOYD@QUB.AC.UK' _publ_section_title ; Absolute configuration assignment and enantiopurity determination of chiral alkaloids and coumarins derived from O- and C-prenyl epoxides. ; #===END data_17 _database_code_CSD 192859 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 O6' _chemical_formula_sum 'C16 H22 O6' _chemical_formula_weight 310.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 '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 6.1170(10) _cell_length_b 13.2620(10) _cell_length_c 19.993(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1621.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 5.5 _cell_measurement_theta_max 28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.808 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6881 _exptl_absorpt_correction_T_max 0.8235 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4 diffractometer' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2854 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1503 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.00 _diffrn_reflns_theta_max 69.94 _reflns_number_total 2808 _reflns_number_gt 2305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^ > 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^)+(0.0527P)^2^+0.1236P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0163(7) _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 0.0(3) _refine_ls_number_reflns 2808 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.001 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 -0.3596(4) -0.04737(17) 0.53195(9) 0.0713(6) Uani 1 1 d . . . C2 C -0.4008(6) -0.1157(2) 0.48355(14) 0.0617(8) Uani 1 1 d . . . O2 O -0.5713(4) -0.16103(18) 0.48185(12) 0.0920(8) Uani 1 1 d . . . C3 C -0.2113(5) -0.12367(19) 0.43831(13) 0.0606(8) Uani 1 1 d . . . H3A H -0.2580 -0.1218 0.3920 0.073 Uiso 1 1 calc R . . H3B H -0.1325 -0.1860 0.4461 0.073 Uiso 1 1 calc R . . C4 C -0.0689(5) -0.03367(18) 0.45436(11) 0.0476(7) Uani 1 1 d . . . H4 H 0.0867 -0.0511 0.4524 0.057 Uiso 1 1 calc R . . C5 C -0.1390(5) -0.0053(2) 0.52582(11) 0.0556(8) Uani 1 1 d . . . C51 C -0.1598(7) 0.1066(2) 0.53838(14) 0.0862(11) Uani 1 1 d . . . H51A H -0.2671 0.1345 0.5087 0.129 Uiso 1 1 calc R . . H51B H -0.0213 0.1386 0.5306 0.129 Uiso 1 1 calc R . . H51C H -0.2040 0.1178 0.5838 0.129 Uiso 1 1 calc R . . C52 C 0.0049(6) -0.0585(3) 0.57616(13) 0.0932(12) Uani 1 1 d . . . H52A H -0.0564 -0.0511 0.6201 0.140 Uiso 1 1 calc R . . H52B H 0.1486 -0.0295 0.5753 0.140 Uiso 1 1 calc R . . H52C H 0.0138 -0.1289 0.5651 0.140 Uiso 1 1 calc R . . O4 O -0.1226(3) 0.04506(12) 0.40731(7) 0.0475(5) Uani 1 1 d . . . C6 C 0.0386(5) 0.1054(2) 0.38739(11) 0.0476(7) Uani 1 1 d . . . O6 O 0.2231(4) 0.09888(19) 0.40487(11) 0.0881(8) Uani 1 1 d . . . C7 C -0.0499(4) 0.18531(17) 0.34129(11) 0.0397(6) Uani 1 1 d . . . O8 O 0.1346(3) 0.24790(12) 0.32027(7) 0.0457(4) Uani 1 1 d . . . C9 C 0.0678(4) 0.29650(17) 0.26348(12) 0.0457(6) Uani 1 1 d . . . O9 O 0.1887(3) 0.35201(14) 0.23380(10) 0.0632(6) Uani 1 1 d . . . C10 C -0.1655(4) 0.26694(18) 0.25066(11) 0.0443(6) Uani 1 1 d . . . C11 C -0.2921(5) 0.31748(19) 0.30914(13) 0.0555(7) Uani 1 1 d . . . H11A H -0.2547 0.3883 0.3129 0.067 Uiso 1 1 calc R . . H11B H -0.4488 0.3113 0.3029 0.067 Uiso 1 1 calc R . . C12 C -0.2162(5) 0.25830(19) 0.37155(12) 0.0519(7) Uani 1 1 d . . . H12A H -0.1487 0.3025 0.4043 0.062 Uiso 1 1 calc R . . H12B H -0.3367 0.2225 0.3923 0.062 Uiso 1 1 calc R . . C13 C -0.2491(5) 0.2922(2) 0.18123(12) 0.0675(9) Uani 1 1 d . . . H13A H -0.2364 0.3634 0.1737 0.101 Uiso 1 1 calc R . . H13B H -0.3996 0.2725 0.1775 0.101 Uiso 1 1 calc R . . H13C H -0.1640 0.2566 0.1485 0.101 Uiso 1 1 calc R . . C14 C -0.1539(4) 0.15462(16) 0.27334(11) 0.0392(6) Uani 1 1 d . . . C15 C 0.0002(5) 0.0909(2) 0.23047(13) 0.0541(7) Uani 1 1 d . . . H15A H 0.0166 0.0254 0.2503 0.081 Uiso 1 1 calc R . . H15B H 0.1403 0.1232 0.2279 0.081 Uiso 1 1 calc R . . H15C H -0.0597 0.0840 0.1863 0.081 Uiso 1 1 calc R . . C16 C -0.3748(4) 0.10304(19) 0.27799(13) 0.0522(7) Uani 1 1 d . . . H16A H -0.3573 0.0377 0.2979 0.078 Uiso 1 1 calc R . . H16B H -0.4354 0.0958 0.2340 0.078 Uiso 1 1 calc R . . H16C H -0.4713 0.1430 0.3050 0.078 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 0.0645(14) 0.0918(15) 0.0576(11) -0.0058(11) 0.0195(11) -0.0120(14) C2 0.061(2) 0.0610(16) 0.0627(17) 0.0127(15) 0.0005(17) -0.0059(18) O2 0.0744(17) 0.0882(16) 0.1134(19) 0.0160(14) -0.0024(15) -0.0252(16) C3 0.084(2) 0.0482(14) 0.0495(13) 0.0020(12) 0.0067(16) 0.0019(16) C4 0.0531(17) 0.0511(13) 0.0386(11) 0.0090(11) 0.0037(13) 0.0059(15) C5 0.0549(19) 0.0728(18) 0.0391(12) -0.0025(13) 0.0038(15) -0.0038(18) C51 0.116(3) 0.082(2) 0.0612(16) -0.0260(16) 0.018(2) -0.012(3) C52 0.098(3) 0.138(3) 0.0440(14) 0.0156(19) -0.0121(19) -0.004(3) O4 0.0482(11) 0.0481(9) 0.0463(9) 0.0088(8) 0.0003(9) -0.0027(10) C6 0.0360(17) 0.0628(16) 0.0439(13) 0.0074(12) 0.0035(13) -0.0025(15) O6 0.0462(14) 0.1125(19) 0.1056(17) 0.0576(15) -0.0063(13) -0.0035(14) C7 0.0337(15) 0.0423(12) 0.0429(12) 0.0019(10) 0.0044(12) -0.0019(12) O8 0.0395(10) 0.0466(9) 0.0509(9) 0.0009(8) 0.0009(9) -0.0076(9) C9 0.0459(16) 0.0393(12) 0.0520(14) 0.0052(12) 0.0072(14) 0.0021(14) O9 0.0574(13) 0.0556(10) 0.0767(12) 0.0194(10) 0.0088(11) -0.0088(11) C10 0.0389(16) 0.0451(13) 0.0490(13) 0.0060(11) 0.0015(13) 0.0029(13) C11 0.0518(18) 0.0464(13) 0.0684(16) 0.0030(13) 0.0045(15) 0.0080(15) C12 0.0528(18) 0.0517(14) 0.0512(13) -0.0085(12) 0.0091(14) 0.0035(15) C13 0.0591(19) 0.083(2) 0.0607(16) 0.0217(16) -0.0064(16) 0.0014(19) C14 0.0368(15) 0.0394(11) 0.0413(11) -0.0008(10) 0.0016(13) 0.0000(13) C15 0.0558(18) 0.0521(15) 0.0545(14) -0.0085(13) 0.0056(15) -0.0010(14) C16 0.0413(16) 0.0565(14) 0.0588(14) 0.0012(13) -0.0004(14) -0.0070(15) _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 1.349(3) . ? O1 C5 1.465(4) . ? C2 O2 1.204(4) . ? C2 C3 1.474(4) . ? C3 C4 1.512(4) . ? C4 O4 1.443(3) . ? C4 C5 1.539(3) . ? C5 C51 1.509(4) . ? C5 C52 1.512(4) . ? O4 C6 1.331(3) . ? C6 O6 1.184(3) . ? C6 C7 1.505(3) . ? C7 O8 1.462(3) . ? C7 C12 1.529(3) . ? C7 C14 1.554(3) . ? O8 C9 1.368(3) . ? C9 O9 1.200(3) . ? C9 C10 1.502(4) . ? C10 C13 1.517(3) . ? C10 C11 1.554(3) . ? C10 C14 1.559(3) . ? C11 C12 1.546(3) . ? C14 C16 1.517(4) . ? C14 C15 1.529(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 C2 O1 C5 111.6(2) . . ? O2 C2 O1 121.1(3) . . ? O2 C2 C3 128.9(3) . . ? O1 C2 C3 110.0(3) . . ? C2 C3 C4 105.4(2) . . ? O4 C4 C3 107.6(2) . . ? O4 C4 C5 111.4(2) . . ? C3 C4 C5 103.3(2) . . ? O1 C5 C51 106.5(3) . . ? O1 C5 C52 107.6(2) . . ? C51 C5 C52 113.4(3) . . ? O1 C5 C4 104.0(2) . . ? C51 C5 C4 114.7(2) . . ? C52 C5 C4 109.9(3) . . ? C6 O4 C4 117.5(2) . . ? O6 C6 O4 125.0(3) . . ? O6 C6 C7 125.1(3) . . ? O4 C6 C7 109.9(2) . . ? O8 C7 C6 107.35(19) . . ? O8 C7 C12 105.53(18) . . ? C6 C7 C12 116.27(19) . . ? O8 C7 C14 102.32(16) . . ? C6 C7 C14 119.9(2) . . ? C12 C7 C14 103.8(2) . . ? C9 O8 C7 106.01(18) . . ? O9 C9 O8 121.0(2) . . ? O9 C9 C10 131.4(2) . . ? O8 C9 C10 107.6(2) . . ? C9 C10 C13 114.8(2) . . ? C9 C10 C11 103.4(2) . . ? C13 C10 C11 115.2(2) . . ? C9 C10 C14 99.0(2) . . ? C13 C10 C14 119.5(2) . . ? C11 C10 C14 102.46(19) . . ? C12 C11 C10 103.80(19) . . ? C7 C12 C11 101.65(19) . . ? C16 C14 C15 109.5(2) . . ? C16 C14 C7 115.41(19) . . ? C15 C14 C7 112.5(2) . . ? C16 C14 C10 114.1(2) . . ? C15 C14 C10 113.2(2) . . ? C7 C14 C10 91.30(17) . . ? 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 C5 O1 C2 O2 177.4(3) . . . . ? C5 O1 C2 C3 -1.8(3) . . . . ? O2 C2 C3 C4 167.3(3) . . . . ? O1 C2 C3 C4 -13.6(3) . . . . ? C2 C3 C4 O4 -95.5(2) . . . . ? C2 C3 C4 C5 22.3(3) . . . . ? C2 O1 C5 C51 137.7(2) . . . . ? C2 O1 C5 C52 -100.5(3) . . . . ? C2 O1 C5 C4 16.1(3) . . . . ? O4 C4 C5 O1 92.1(3) . . . . ? C3 C4 C5 O1 -23.1(3) . . . . ? O4 C4 C5 C51 -23.8(4) . . . . ? C3 C4 C5 C51 -138.9(3) . . . . ? O4 C4 C5 C52 -153.0(3) . . . . ? C3 C4 C5 C52 91.9(3) . . . . ? C3 C4 O4 C6 -145.7(2) . . . . ? C5 C4 O4 C6 101.8(3) . . . . ? C4 O4 C6 O6 0.7(4) . . . . ? C4 O4 C6 C7 -177.33(18) . . . . ? O6 C6 C7 O8 2.9(4) . . . . ? O4 C6 C7 O8 -179.03(18) . . . . ? O6 C6 C7 C12 -114.9(3) . . . . ? O4 C6 C7 C12 63.1(3) . . . . ? O6 C6 C7 C14 118.8(3) . . . . ? O4 C6 C7 C14 -63.1(3) . . . . ? C6 C7 O8 C9 160.55(18) . . . . ? C12 C7 O8 C9 -74.8(2) . . . . ? C14 C7 O8 C9 33.5(2) . . . . ? C7 O8 C9 O9 -178.3(2) . . . . ? C7 O8 C9 C10 2.4(2) . . . . ? O9 C9 C10 C13 15.4(4) . . . . ? O8 C9 C10 C13 -165.4(2) . . . . ? O9 C9 C10 C11 -110.9(3) . . . . ? O8 C9 C10 C11 68.3(2) . . . . ? O9 C9 C10 C14 143.9(3) . . . . ? O8 C9 C10 C14 -36.9(2) . . . . ? C9 C10 C11 C12 -68.5(2) . . . . ? C13 C10 C11 C12 165.5(2) . . . . ? C14 C10 C11 C12 34.1(3) . . . . ? O8 C7 C12 C11 68.7(2) . . . . ? C6 C7 C12 C11 -172.5(2) . . . . ? C14 C7 C12 C11 -38.5(2) . . . . ? C10 C11 C12 C7 2.4(3) . . . . ? O8 C7 C14 C16 -169.98(18) . . . . ? C6 C7 C14 C16 71.5(3) . . . . ? C12 C7 C14 C16 -60.4(2) . . . . ? O8 C7 C14 C15 63.4(2) . . . . ? C6 C7 C14 C15 -55.1(3) . . . . ? C12 C7 C14 C15 173.02(19) . . . . ? O8 C7 C14 C10 -52.4(2) . . . . ? C6 C7 C14 C10 -170.9(2) . . . . ? C12 C7 C14 C10 57.2(2) . . . . ? C9 C10 C14 C16 170.6(2) . . . . ? C13 C10 C14 C16 -64.2(3) . . . . ? C11 C10 C14 C16 64.5(2) . . . . ? C9 C10 C14 C15 -63.4(2) . . . . ? C13 C10 C14 C15 61.9(3) . . . . ? C11 C10 C14 C15 -169.4(2) . . . . ? C9 C10 C14 C7 51.8(2) . . . . ? C13 C10 C14 C7 177.1(2) . . . . ? C11 C10 C14 C7 -54.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 69.94 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.141 _refine_diff_density_min -0.119 _refine_diff_density_rms 0.027 #===END