# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1540 data_0395s _audit_creation_method SHELXL-97 _publ_section_experimental ; The data collection nominally covered a sphere of reciprocal space, by a combination of five sets of exposures; each set had a different \f angle for the crystal and each exposure covered 0.3\% in \w. The crystal-to-detector distance was 4.935 cm. data measured to a \q maximum of 28.99\%. Data for refinement truncated at 0.80\A (26.37\% in \q, 99.8% complete). Crystal decay was monitored by repeating the first 50 frames at the end of data collection and analyzing the duplicate reflections. ; _publ_section_exptl_refinement ; All hydrogen atoms bar H3B and H5C were placed geometrically and refined with a riding model (including free rotation about C---C bonds for methyl groups), and with U~iso~ constrained to be 1.2 (1.5 for methyl groups) times U~eq~ of the carrier atom. Area detector scaling corrections were performed by SADABS. This correction was used to scale the frames of data and to correct for absorption of the primary beam by the crystal support using the method of Blessing (1995). A correction for absorption of the primary beam by the crystal was not applied and as such no transmission factors are quoted. ; _publ_section_references ; Blessing R.H. (1995). Acta Cryst., A51, 33-38. Bruker AXS (1998). SMART, SAINT and SADABS area-detector control and integration software. Bruker AXS Inc., Madison, WI 53719, U.S.A. Sheldrick, G.M. (1998). SHELXTL Version 5.10 Bruker AXS Inc., Madison, WI 53719, U.S.A. ; _chemical_name_systematic ; ? ; _chemical_name_common '(-)-Nemorensic Acid' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H16 O5' _chemical_formula_weight 216.23 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) 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 8.4556(2) _cell_length_b 11.4227(2) _cell_length_c 11.4637(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1107.23(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 7281 _cell_measurement_theta_min 2.517 _cell_measurement_theta_max 28.985 _exptl_crystal_description Fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type 'see text' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _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 AXS 1K SMART CCD area detector' _diffrn_measurement_method 'narrow frame omega scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 'see text' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9403 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2269 _reflns_number_gt 2182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5 (Bruker AXS, 1998)' _computing_cell_refinement 'SMART V5 & SAINT V5 (Bruker AXS, 1998)' _computing_data_reduction 'SAINT V5 (Bruker AXS, 1998)' _computing_structure_solution 'SHELXTL V5.10 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL V5.10 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL V5.10 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL V5.10 (Sheldrick, 1998)' _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^)+(0.0650P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881 Absolute structure not determined' _refine_ls_abs_structure_Flack -0.2(7) #Absolute structure not determined _refine_ls_number_reflns 2269 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 O1 O 1.37564(9) 0.66690(7) 0.71071(6) 0.02002(18) Uani 1 1 d . . . O2 O 0.95148(11) 0.56033(7) 0.62452(7) 0.02441(19) Uani 1 1 d . . . O3 O 1.13353(11) 0.49027(7) 0.74141(8) 0.0279(2) Uani 1 1 d . . . H3B H 1.224(3) 0.5127(16) 0.7950(17) 0.051(5) Uiso 1 1 d . . . O4 O 1.35306(11) 0.53194(7) 0.90008(8) 0.0272(2) Uani 1 1 d . . . O5 O 1.55491(12) 0.62129(8) 0.98744(7) 0.0294(2) Uani 1 1 d . . . H5C H 1.547(2) 0.5645(14) 1.0370(16) 0.044(5) Uiso 1 1 d . . . C1 C 1.24812(13) 0.74741(9) 0.68466(10) 0.0202(2) Uani 1 1 d . . . C2 C 1.29924(15) 0.86039(10) 0.74456(10) 0.0234(3) Uani 1 1 d . . . H2A H 1.2067 0.9098 0.7638 0.027(4) Uiso 1 1 calc R . . H2B H 1.3725 0.9057 0.6945 0.035(4) Uiso 1 1 calc R . . C3 C 1.38218(14) 0.81809(9) 0.85501(10) 0.0223(2) Uani 1 1 d . . . H3A H 1.2991 0.7940 0.9122 0.031(4) Uiso 1 1 calc R . . C4 C 1.46576(13) 0.70518(10) 0.80992(9) 0.0197(2) Uani 1 1 d . . . C5 C 1.09281(13) 0.70087(10) 0.73936(10) 0.0209(2) Uani 1 1 d . . . H5A H 1.1033 0.7003 0.8254 0.023(3) Uiso 1 1 calc R . . H5B H 1.0049 0.7543 0.7189 0.025(4) Uiso 1 1 calc R . . C6 C 1.05370(14) 0.57875(10) 0.69764(10) 0.0204(2) Uani 1 1 d . . . C7 C 1.23434(15) 0.75465(11) 0.55263(11) 0.0271(3) Uani 1 1 d . . . H7A H 1.3329 0.7858 0.5201 0.050(5) Uiso 1 1 calc R . . H7B H 1.1464 0.8065 0.5318 0.047(4) Uiso 1 1 calc R . . H7C H 1.2149 0.6763 0.5209 0.043(4) Uiso 1 1 calc R . . C8 C 1.48767(17) 0.90925(11) 0.91380(12) 0.0312(3) Uani 1 1 d . . . H8A H 1.4223 0.9740 0.9425 0.052(5) Uiso 1 1 calc R . . H8B H 1.5646 0.9392 0.8572 0.033(4) Uiso 1 1 calc R . . H8C H 1.5438 0.8731 0.9793 0.054(5) Uiso 1 1 calc R . . C9 C 1.63680(14) 0.72208(11) 0.77096(10) 0.0261(3) Uani 1 1 d . . . H9A H 1.6757 0.6496 0.7352 0.023(3) Uiso 1 1 calc R . . H9B H 1.7024 0.7416 0.8387 0.031(4) Uiso 1 1 calc R . . H9C H 1.6422 0.7859 0.7139 0.029(4) Uiso 1 1 calc R . . C10 C 1.45178(14) 0.60978(10) 0.90246(10) 0.0209(2) 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 O1 0.0205(4) 0.0191(4) 0.0205(4) -0.0015(3) 0.0003(3) 0.0022(3) O2 0.0220(4) 0.0270(4) 0.0242(4) -0.0010(3) -0.0019(3) -0.0006(3) O3 0.0260(4) 0.0196(4) 0.0382(5) 0.0022(4) -0.0088(4) -0.0023(3) O4 0.0259(4) 0.0237(4) 0.0319(4) 0.0078(3) -0.0062(4) -0.0062(3) O5 0.0310(5) 0.0294(5) 0.0277(5) 0.0070(4) -0.0080(4) -0.0095(4) C1 0.0203(5) 0.0181(5) 0.0222(6) 0.0024(4) 0.0012(4) 0.0015(4) C2 0.0260(6) 0.0162(5) 0.0280(6) 0.0012(4) 0.0020(5) -0.0006(4) C3 0.0245(6) 0.0180(5) 0.0245(5) -0.0020(4) 0.0040(5) -0.0025(5) C4 0.0193(5) 0.0198(5) 0.0199(5) -0.0010(4) 0.0012(5) -0.0012(4) C5 0.0194(5) 0.0201(5) 0.0233(5) -0.0015(4) 0.0032(4) -0.0001(4) C6 0.0170(5) 0.0225(6) 0.0217(5) 0.0007(4) 0.0046(5) -0.0013(4) C7 0.0301(6) 0.0281(6) 0.0232(6) 0.0052(5) 0.0012(5) -0.0027(5) C8 0.0385(7) 0.0241(6) 0.0311(6) -0.0055(5) -0.0019(5) -0.0074(5) C9 0.0211(6) 0.0294(6) 0.0278(6) 0.0008(5) 0.0047(5) -0.0030(5) C10 0.0182(5) 0.0207(5) 0.0238(5) -0.0003(4) 0.0020(4) 0.0007(5) _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 C4 1.4372(13) . yes O1 C1 1.4483(13) . yes O2 C6 1.2222(14) . yes O3 C6 1.3148(14) . yes O4 C10 1.2199(15) . yes O5 C10 1.3140(14) . yes C1 C7 1.5202(16) . yes C1 C2 1.5244(16) . yes C1 C5 1.5494(15) . yes C2 C3 1.5260(17) . yes C3 C8 1.5278(17) . yes C3 C4 1.5588(15) . yes C4 C10 1.5254(15) . yes C4 C9 1.5259(16) . yes C5 C6 1.5113(15) . yes O3 H3B 1.01(2) . yes O5 H5C 0.865(18) . yes C2 H2A 0.9900 . no C2 H2B 0.9900 . no C3 H3A 1.0000 . no C5 H5A 0.9900 . no C5 H5B 0.9900 . no C7 H7A 0.9800 . no C7 H7B 0.9800 . no C7 H7C 0.9800 . no C8 H8A 0.9800 . no C8 H8B 0.9800 . no C8 H8C 0.9800 . no C9 H9A 0.9800 . no C9 H9B 0.9800 . no C9 H9C 0.9800 . no 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 C4 O1 C1 111.39(8) . . yes O1 C1 C7 107.27(10) . . yes O1 C1 C2 103.50(9) . . yes C7 C1 C2 115.10(9) . . yes O1 C1 C5 109.25(9) . . yes C7 C1 C5 110.90(10) . . yes C2 C1 C5 110.40(9) . . yes C1 C2 C3 103.65(9) . . yes C2 C3 C8 114.74(10) . . yes C2 C3 C4 101.26(9) . . yes C8 C3 C4 116.46(10) . . yes O1 C4 C10 106.97(9) . . yes O1 C4 C9 108.02(9) . . yes C10 C4 C9 111.55(10) . . yes O1 C4 C3 105.89(9) . . yes C10 C4 C3 108.99(9) . . yes C9 C4 C3 114.97(9) . . yes C6 C5 C1 111.97(9) . . yes O2 C6 O3 119.50(10) . . yes O2 C6 C5 122.05(10) . . yes O3 C6 C5 118.45(10) . . yes O4 C10 O5 122.93(10) . . yes O4 C10 C4 123.93(10) . . yes O5 C10 C4 113.12(9) . . yes C6 O3 H3B 115.1(11) . . yes C10 O5 H5C 111.4(12) . . yes C1 C2 H2A 111.0 . . no C3 C2 H2A 111.0 . . no C1 C2 H2B 111.0 . . no C3 C2 H2B 111.0 . . no H2A C2 H2B 109.0 . . no C2 C3 H3A 108.0 . . no C8 C3 H3A 108.0 . . no C4 C3 H3A 108.0 . . no C6 C5 H5A 109.2 . . no C1 C5 H5A 109.2 . . no C6 C5 H5B 109.2 . . no C1 C5 H5B 109.2 . . no H5A C5 H5B 107.9 . . no C1 C7 H7A 109.5 . . no C1 C7 H7B 109.5 . . no H7A C7 H7B 109.5 . . no C1 C7 H7C 109.5 . . no H7A C7 H7C 109.5 . . no H7B C7 H7C 109.5 . . no C3 C8 H8A 109.5 . . no C3 C8 H8B 109.5 . . no H8A C8 H8B 109.5 . . no C3 C8 H8C 109.5 . . no H8A C8 H8C 109.5 . . no H8B C8 H8C 109.5 . . no C4 C9 H9A 109.5 . . no C4 C9 H9B 109.5 . . no H9A C9 H9B 109.5 . . no C4 C9 H9C 109.5 . . no H9A C9 H9C 109.5 . . no H9B C9 H9C 109.5 . . no 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 C4 O1 C1 C7 142.32(9) . . . . no C4 O1 C1 C2 20.22(11) . . . . no C4 O1 C1 C5 -97.40(10) . . . . no O1 C1 C2 C3 -35.48(11) . . . . no C7 C1 C2 C3 -152.20(11) . . . . no C5 C1 C2 C3 81.33(11) . . . . no C1 C2 C3 C8 162.67(10) . . . . no C1 C2 C3 C4 36.38(11) . . . . no C1 O1 C4 C10 119.08(9) . . . . no C1 O1 C4 C9 -120.70(10) . . . . no C1 O1 C4 C3 2.94(11) . . . . no C2 C3 C4 O1 -24.63(11) . . . . no C8 C3 C4 O1 -149.78(9) . . . . no C2 C3 C4 C10 -139.40(9) . . . . no C8 C3 C4 C10 95.45(12) . . . . no C2 C3 C4 C9 94.53(11) . . . . no C8 C3 C4 C9 -30.62(14) . . . . no O1 C1 C5 C6 -56.66(12) . . . . no C7 C1 C5 C6 61.37(12) . . . . no C2 C1 C5 C6 -169.85(9) . . . . no C1 C5 C6 O2 -103.41(12) . . . . no C1 C5 C6 O3 76.16(13) . . . . no O1 C4 C10 O4 -15.37(15) . . . . no C9 C4 C10 O4 -133.30(12) . . . . no C3 C4 C10 O4 98.69(13) . . . . no O1 C4 C10 O5 166.24(9) . . . . no C9 C4 C10 O5 48.31(13) . . . . no C3 C4 C10 O5 -79.70(12) . . . . no 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 H3B O4 1.01(2) 1.64(2) 2.6422(13) 168.9(18) . O5 H5C O2 0.865(18) 1.744(18) 2.6032(12) 172.4(18) 2_765 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.213 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.034