# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Silvia M. C. S. Monteiro' 'Armando J. D. Silvestre' 'Artur M. S. Silva' 'Jose A. S. Cavaleiro' 'Vitor Felix' 'Michael G. B. Drew' _publ_contact_letter ? _publ_contact_author_email 'JCAVALEIRO@DQ.UA.PT' _publ_contact_author 'Prof Jose A S Cavaleiro' _publ_contact_author_adress ; Prof Jose A S Cavaleiro Department of Chemistry University of Aveiro Aveiro 3810-193 PORTUGAL ; #------------------------- data section of block --------------------------- data_compound_12 _database_code_CSD 163568 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 13-isopropyl-7-oxo-podocarpe-5,8,11,13-tetraen-4,6-carbolactone 12 ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 O3' _chemical_formula_weight 310.38 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 Orthorrombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, -y, z+1/2' _cell_length_a 8.776(11) _cell_length_b 10.233(16) _cell_length_c 18.853(24) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1693(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5667 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.03 _reflns_number_total 3167 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.1168P)^2^+0.4972P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(5) _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 2(3) _refine_ls_number_reflns 3167 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1163 _refine_ls_R_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.2296 _refine_ls_wR_factor_gt 0.2126 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3545(5) 0.1650(5) 0.0656(3) 0.0468(11) Uani 1 d . . . H1A H 0.2461 0.1468 0.0666 0.056 Uiso 1 calc R . . H1B H 0.3737 0.2241 0.0264 0.056 Uiso 1 calc R . . C2 C 0.4405(5) 0.0369(5) 0.0522(3) 0.0492(12) Uani 1 d . . . H2A H 0.4147 -0.0254 0.0891 0.059 Uiso 1 calc R . . H2B H 0.4081 0.0005 0.0072 0.059 Uiso 1 calc R . . C3 C 0.6131(5) 0.0568(5) 0.0510(3) 0.0487(12) Uani 1 d . . . H3A H 0.6401 0.1163 0.0130 0.058 Uiso 1 calc R . . H3B H 0.6633 -0.0261 0.0422 0.058 Uiso 1 calc R . . C4 C 0.6679(4) 0.1133(5) 0.1229(2) 0.0418(10) Uani 1 d . . . C5 C 0.5708(4) 0.2338(4) 0.1363(2) 0.0334(9) Uani 1 d . . . C6 C 0.6573(4) 0.3386(4) 0.1290(2) 0.0383(9) Uani 1 d . . . C7 C 0.6041(4) 0.4731(5) 0.1243(2) 0.0437(11) Uani 1 d . . . C8 C 0.4351(4) 0.4864(4) 0.1283(2) 0.0368(9) Uani 1 d . . . C9 C 0.3407(4) 0.3751(4) 0.1349(2) 0.0364(9) Uani 1 d . . . C10 C 0.4005(4) 0.2352(4) 0.1371(2) 0.0349(9) Uani 1 d . . . C11 C 0.1825(5) 0.3978(5) 0.1390(2) 0.0419(10) Uani 1 d . . . H11 H 0.1170 0.3270 0.1440 0.050 Uiso 1 calc R . . C12 C 0.1226(5) 0.5216(5) 0.1357(2) 0.0433(11) Uani 1 d . . . H12 H 0.0176 0.5323 0.1390 0.052 Uiso 1 calc R . . C13 C 0.2156(5) 0.6330(4) 0.1274(2) 0.0415(10) Uani 1 d . . . C14 C 0.3710(5) 0.6103(5) 0.1245(3) 0.0457(11) Uani 1 d . . . H14 H 0.4358 0.6817 0.1197 0.055 Uiso 1 calc R . . C15 C 0.8242(5) 0.1765(5) 0.1140(3) 0.0504(12) Uani 1 d . . . C16 C 0.6775(6) 0.0072(6) 0.1806(3) 0.0563(13) Uani 1 d . . . H16A H 0.7002 0.0472 0.2254 0.068 Uiso 1 calc R . . H16B H 0.7564 -0.0539 0.1687 0.068 Uiso 1 calc R . . H16C H 0.5817 -0.0378 0.1837 0.068 Uiso 1 calc R . . C17 C 0.3354(5) 0.1610(4) 0.2018(2) 0.0527(12) Uani 1 d . . . H17A H 0.3740 0.0733 0.2021 0.063 Uiso 1 calc R . . H17B H 0.2262 0.1591 0.1988 0.063 Uiso 1 calc R . . H17C H 0.3655 0.2047 0.2446 0.063 Uiso 1 calc R . . C18 C 0.1486(5) 0.7693(4) 0.1241(2) 0.0567(13) Uani 1 d R . . H18 H 0.2339 0.8295 0.1166 0.068 Uiso 1 calc R . . C19 C 0.0741(11) 0.8082(9) 0.1936(4) 0.110(3) Uani 1 d . . . H19A H -0.0127 0.7533 0.2021 0.132 Uiso 1 calc R . . H19B H 0.0419 0.8978 0.1909 0.132 Uiso 1 calc R . . H19C H 0.1460 0.7983 0.2316 0.132 Uiso 1 calc R . . C20 C 0.0417(11) 0.7881(8) 0.0634(4) 0.113(3) Uani 1 d . . . H20A H 0.0868 0.7537 0.0210 0.135 Uiso 1 calc R . . H20B H 0.0216 0.8796 0.0573 0.135 Uiso 1 calc R . . H20C H -0.0520 0.7430 0.0730 0.135 Uiso 1 calc R . . O71 O 0.6907(4) 0.5682(4) 0.1178(2) 0.0647(11) Uani 1 d . . . O151 O 0.9456(4) 0.1257(4) 0.1042(2) 0.0699(12) Uani 1 d . . . O152 O 0.8118(3) 0.3108(3) 0.11726(18) 0.0489(8) Uani 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 0.032(2) 0.054(3) 0.055(3) -0.006(2) -0.0071(18) -0.006(2) C2 0.042(2) 0.041(3) 0.064(3) -0.010(2) -0.004(2) -0.006(2) C3 0.045(3) 0.047(3) 0.055(3) -0.007(2) 0.006(2) -0.002(2) C4 0.031(2) 0.051(3) 0.043(2) 0.002(2) 0.0001(18) 0.0023(18) C5 0.0247(18) 0.047(3) 0.029(2) -0.0007(19) -0.0023(14) -0.0010(16) C6 0.0274(19) 0.047(3) 0.041(2) -0.006(2) -0.0005(16) 0.0055(17) C7 0.033(2) 0.054(3) 0.044(3) -0.003(2) 0.0027(19) -0.009(2) C8 0.035(2) 0.040(2) 0.036(2) 0.002(2) 0.0038(17) 0.0016(17) C9 0.034(2) 0.043(2) 0.032(2) 0.0035(19) -0.0007(16) -0.0010(17) C10 0.0276(19) 0.040(2) 0.038(2) 0.003(2) 0.0034(15) -0.0007(17) C11 0.033(2) 0.045(3) 0.047(3) 0.000(2) 0.0035(18) -0.0051(19) C12 0.032(2) 0.049(3) 0.049(3) 0.002(2) 0.0039(19) 0.0042(19) C13 0.044(2) 0.038(3) 0.043(2) 0.002(2) 0.0048(19) 0.0051(18) C14 0.037(2) 0.049(3) 0.052(3) 0.002(2) 0.0086(19) -0.0040(19) C15 0.034(2) 0.057(3) 0.060(3) -0.001(2) 0.001(2) 0.005(2) C16 0.051(3) 0.058(3) 0.061(3) 0.012(3) 0.000(2) 0.015(2) C17 0.048(3) 0.049(3) 0.060(3) 0.012(2) 0.019(2) 0.001(2) C18 0.044(2) 0.048(3) 0.077(3) -0.002(3) 0.005(2) 0.004(2) C19 0.159(8) 0.095(6) 0.075(4) -0.020(4) -0.001(5) 0.055(6) C20 0.186(8) 0.071(5) 0.081(5) 0.006(4) -0.040(5) 0.049(5) O71 0.0393(18) 0.050(2) 0.105(3) 0.002(2) 0.0103(19) -0.0094(14) O151 0.0292(18) 0.067(3) 0.113(3) -0.005(2) 0.0051(17) 0.0097(16) O152 0.0259(15) 0.052(2) 0.069(2) -0.0037(16) 0.0021(13) 0.0013(13) _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 C1 C2 1.533(7) . ? C1 C10 1.579(6) . ? C2 C3 1.529(6) . ? C3 C4 1.549(7) . ? C4 C5 1.520(6) . ? C4 C15 1.526(6) . ? C4 C16 1.539(7) . ? C5 C6 1.321(6) . ? C5 C10 1.494(5) . ? C6 O152 1.403(5) . ? C6 C7 1.457(7) . ? C7 O71 1.241(6) . ? C7 C8 1.491(6) . ? C8 C14 1.389(7) . ? C8 C9 1.413(6) . ? C9 C11 1.410(6) . ? C9 C10 1.526(7) . ? C10 C17 1.546(5) . ? C11 C12 1.373(7) . ? C12 C13 1.411(6) . ? C13 C14 1.384(6) . ? C13 C18 1.514(6) . ? C15 O151 1.200(6) . ? C15 O152 1.380(6) . ? C18 C20 1.492(8) . ? C18 C19 1.516(8) . ? 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 C10 113.8(4) . . ? C3 C2 C1 112.1(4) . . ? C2 C3 C4 110.2(4) . . ? C5 C4 C15 100.3(4) . . ? C5 C4 C16 119.0(4) . . ? C15 C4 C16 109.1(4) . . ? C5 C4 C3 105.9(3) . . ? C15 C4 C3 110.0(4) . . ? C16 C4 C3 111.8(4) . . ? C6 C5 C10 124.6(4) . . ? C6 C5 C4 108.6(3) . . ? C10 C5 C4 124.7(4) . . ? C5 C6 O152 114.0(4) . . ? C5 C6 C7 126.1(4) . . ? O152 C6 C7 119.5(4) . . ? O71 C7 C6 123.4(4) . . ? O71 C7 C8 122.9(4) . . ? C6 C7 C8 113.7(4) . . ? C14 C8 C9 120.2(4) . . ? C14 C8 C7 118.9(4) . . ? C9 C8 C7 120.9(4) . . ? C11 C9 C8 116.7(4) . . ? C11 C9 C10 119.4(4) . . ? C8 C9 C10 123.9(3) . . ? C5 C10 C9 110.6(4) . . ? C5 C10 C17 111.9(3) . . ? C9 C10 C17 110.8(3) . . ? C5 C10 C1 104.1(3) . . ? C9 C10 C1 108.4(3) . . ? C17 C10 C1 110.8(4) . . ? C12 C11 C9 121.8(4) . . ? C11 C12 C13 121.9(4) . . ? C14 C13 C12 116.0(4) . . ? C14 C13 C18 122.4(4) . . ? C12 C13 C18 121.6(4) . . ? C13 C14 C8 123.4(4) . . ? O151 C15 O152 120.6(4) . . ? O151 C15 C4 129.1(5) . . ? O152 C15 C4 110.3(4) . . ? C20 C18 C13 113.2(5) . . ? C20 C18 C19 110.9(5) . . ? C13 C18 C19 112.0(4) . . ? C15 O152 C6 106.6(3) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.327 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.088