# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_requested_category FO _publ_contact_author_name 'Tom McCabe' _publ_contact_author_email tmccabe@tcd.ie loop_ _publ_author_name N.Geraghty T.McMurry data_mcmcs _database_code_depnum_ccdc_archive 'CCDC 735146' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 O3' _chemical_formula_weight 284.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6572(9) _cell_length_b 9.8399(8) _cell_length_c 12.3209(15) _cell_angle_alpha 102.795(8) _cell_angle_beta 99.112(11) _cell_angle_gamma 105.356(9) _cell_volume 738.47(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9503 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_process_details Sadabs _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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2763 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2529 _reflns_number_gt 1396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxtl _computing_publication_material Shelxtl _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^)+(0.0581P)^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_number_reflns 2529 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1289 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.006 _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 O2 O 0.7039(4) 0.4912(2) 0.85995(18) 0.0592(6) Uani 1 1 d . . . O3 O 1.0758(3) 0.7487(2) 0.85689(17) 0.0540(6) Uani 1 1 d . . . C1 C 0.7874(5) 0.9930(3) 0.7799(3) 0.0498(8) Uani 1 1 d . . . C2 C 0.9085(5) 0.8787(3) 0.7491(2) 0.0411(7) Uani 1 1 d . . . C3 C 0.9182(4) 0.7822(3) 0.8251(2) 0.0377(6) Uani 1 1 d . . . C4 C 0.7099(4) 0.7317(3) 0.8622(2) 0.0383(7) Uani 1 1 d . . . C5 C 0.5167(5) 0.6683(3) 0.7568(2) 0.0437(7) Uani 1 1 d . . . C6 C 0.5833(5) 0.6578(3) 0.6430(3) 0.0454(7) Uani 1 1 d . . . C7 C 0.7344(4) 0.8013(3) 0.6340(2) 0.0413(7) Uani 1 1 d . . . C8 C 0.6473(6) 0.9346(4) 0.6577(3) 0.0563(9) Uani 1 1 d . . . C9 C 0.6708(6) 0.9856(4) 0.8781(3) 0.0549(9) Uani 1 1 d . . . C10 C 0.6976(6) 0.8732(3) 0.9416(3) 0.0506(8) Uani 1 1 d . . . C11 C 0.7300(5) 0.6225(3) 0.9294(3) 0.0471(7) Uani 1 1 d . . . C12 C 0.7199(6) 0.3774(4) 0.9134(3) 0.0760(11) Uani 1 1 d . . . H12A H 0.8675 0.3928 0.9464 0.114 Uiso 1 1 calc R . . H12B H 0.6618 0.2838 0.8572 0.114 Uiso 1 1 calc R . . H12C H 0.6411 0.3796 0.9723 0.114 Uiso 1 1 calc R . . C13 C 0.8166(5) 0.7693(3) 0.5268(2) 0.0446(7) Uani 1 1 d . . . C14 C 0.7222(6) 0.7913(4) 0.4269(3) 0.0608(9) Uani 1 1 d . . . C15 C 0.7899(7) 0.7504(4) 0.3268(3) 0.0725(11) Uani 1 1 d . . . C16 C 0.9495(7) 0.6879(4) 0.3256(3) 0.0681(10) Uani 1 1 d . . . C17 C 1.0459(6) 0.6671(4) 0.4243(3) 0.0687(10) Uani 1 1 d . . . C18 C 0.9802(5) 0.7077(4) 0.5244(3) 0.0583(9) Uani 1 1 d . . . H1 H 0.884(5) 1.093(3) 0.796(2) 0.055(8) Uiso 1 1 d . . . H2 H 1.048(4) 0.928(3) 0.7394(19) 0.036(7) Uiso 1 1 d . . . H5A H 0.442(4) 0.568(3) 0.754(2) 0.045(7) Uiso 1 1 d . . . H5B H 0.422(4) 0.729(3) 0.763(2) 0.048(8) Uiso 1 1 d . . . H6A H 0.654(4) 0.576(3) 0.629(2) 0.051(8) Uiso 1 1 d . . . H6B H 0.455(5) 0.625(3) 0.581(2) 0.058(9) Uiso 1 1 d . . . H8A H 0.504(5) 0.908(3) 0.647(2) 0.050(9) Uiso 1 1 d . . . H8B H 0.689(6) 0.993(4) 0.608(3) 0.084(12) Uiso 1 1 d . . . H9A H 0.717(5) 1.078(4) 0.930(3) 0.065(10) Uiso 1 1 d . . . H9B H 0.521(5) 0.972(3) 0.844(2) 0.066(10) Uiso 1 1 d . . . H10A H 0.832(5) 0.915(3) 1.005(2) 0.057(9) Uiso 1 1 d . . . H10B H 0.586(6) 0.845(3) 0.977(3) 0.075(11) Uiso 1 1 d . . . H14 H 0.600(5) 0.831(3) 0.424(2) 0.064(10) Uiso 1 1 d . . . H15 H 0.726(5) 0.772(3) 0.264(3) 0.064(9) Uiso 1 1 d . . . H16 H 0.993(6) 0.656(4) 0.249(3) 0.101(12) Uiso 1 1 d . . . H17 H 1.158(6) 0.616(4) 0.421(3) 0.099(13) Uiso 1 1 d . . . H18 H 1.059(5) 0.695(3) 0.597(3) 0.065(9) Uiso 1 1 d . . . O1 O 0.7681(4) 0.6501(3) 1.03156(19) 0.0720(7) 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 O2 0.0734(15) 0.0445(13) 0.0732(15) 0.0273(12) 0.0255(12) 0.0263(11) O3 0.0432(12) 0.0667(14) 0.0632(14) 0.0251(11) 0.0184(10) 0.0258(11) C1 0.062(2) 0.0339(17) 0.057(2) 0.0121(15) 0.0207(17) 0.0170(16) C2 0.0380(17) 0.0380(15) 0.0475(18) 0.0124(14) 0.0162(14) 0.0080(14) C3 0.0365(16) 0.0379(15) 0.0341(15) 0.0004(12) 0.0074(13) 0.0123(13) C4 0.0375(16) 0.0406(15) 0.0424(16) 0.0129(13) 0.0160(13) 0.0164(13) C5 0.0370(17) 0.0368(17) 0.059(2) 0.0134(14) 0.0135(15) 0.0137(14) C6 0.0409(18) 0.0428(17) 0.0491(19) 0.0086(14) 0.0073(16) 0.0125(15) C7 0.0417(16) 0.0389(16) 0.0457(17) 0.0133(13) 0.0102(14) 0.0150(13) C8 0.057(2) 0.055(2) 0.067(2) 0.0259(18) 0.0152(19) 0.0271(18) C9 0.066(2) 0.0439(19) 0.063(2) 0.0106(17) 0.0251(19) 0.0282(18) C10 0.055(2) 0.0470(18) 0.055(2) 0.0101(16) 0.0254(19) 0.0194(16) C11 0.0431(17) 0.0549(19) 0.054(2) 0.0203(16) 0.0219(16) 0.0220(15) C12 0.074(2) 0.064(2) 0.120(3) 0.058(2) 0.036(2) 0.037(2) C13 0.0534(18) 0.0433(16) 0.0377(17) 0.0142(13) 0.0119(14) 0.0128(14) C14 0.066(2) 0.069(2) 0.050(2) 0.0244(18) 0.0084(18) 0.0211(19) C15 0.084(3) 0.083(3) 0.045(2) 0.031(2) 0.007(2) 0.009(2) C16 0.083(3) 0.065(2) 0.053(2) 0.0149(18) 0.030(2) 0.010(2) C17 0.076(3) 0.076(3) 0.059(2) 0.0138(19) 0.028(2) 0.028(2) C18 0.065(2) 0.072(2) 0.047(2) 0.0156(17) 0.0181(18) 0.0321(19) O1 0.0897(18) 0.0939(18) 0.0542(15) 0.0322(13) 0.0272(13) 0.0487(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 O2 C11 1.332(3) . ? O2 C12 1.438(3) . ? O3 C3 1.214(3) . ? C1 C8 1.535(5) . ? C1 C9 1.542(4) . ? C1 C2 1.565(4) . ? C2 C3 1.479(4) . ? C2 C7 1.571(4) . ? C3 C4 1.521(4) . ? C4 C11 1.515(4) . ? C4 C10 1.544(4) . ? C4 C5 1.555(4) . ? C5 C6 1.527(4) . ? C6 C7 1.539(4) . ? C7 C13 1.510(4) . ? C7 C8 1.558(4) . ? C9 C10 1.521(4) . ? C11 O1 1.197(3) . ? C13 C14 1.380(4) . ? C13 C18 1.380(4) . ? C14 C15 1.391(5) . ? C15 C16 1.362(5) . ? C16 C17 1.365(5) . ? C17 C18 1.385(4) . ? 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 C11 O2 C12 116.6(2) . . ? C8 C1 C9 116.9(3) . . ? C8 C1 C2 89.4(2) . . ? C9 C1 C2 117.7(2) . . ? C3 C2 C1 116.3(2) . . ? C3 C2 C7 113.1(2) . . ? C1 C2 C7 89.3(2) . . ? O3 C3 C2 124.1(3) . . ? O3 C3 C4 123.1(2) . . ? C2 C3 C4 112.7(2) . . ? C11 C4 C3 108.3(2) . . ? C11 C4 C10 110.0(2) . . ? C3 C4 C10 103.7(2) . . ? C11 C4 C5 113.0(2) . . ? C3 C4 C5 110.6(2) . . ? C10 C4 C5 110.9(2) . . ? C6 C5 C4 113.2(2) . . ? C5 C6 C7 114.8(2) . . ? C13 C7 C6 109.0(2) . . ? C13 C7 C8 117.8(2) . . ? C6 C7 C8 114.3(3) . . ? C13 C7 C2 116.3(2) . . ? C6 C7 C2 109.8(2) . . ? C8 C7 C2 88.4(2) . . ? C1 C8 C7 90.9(2) . . ? C10 C9 C1 116.2(3) . . ? C9 C10 C4 112.5(3) . . ? O1 C11 O2 124.0(3) . . ? O1 C11 C4 124.9(3) . . ? O2 C11 C4 111.1(3) . . ? C14 C13 C18 118.1(3) . . ? C14 C13 C7 121.3(3) . . ? C18 C13 C7 120.5(3) . . ? C13 C14 C15 120.3(4) . . ? C16 C15 C14 120.8(4) . . ? C15 C16 C17 119.4(4) . . ? C16 C17 C18 120.3(4) . . ? C13 C18 C17 121.1(3) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.161 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.042 # Attachment 'bscbs.cif' data_bscbs _database_code_depnum_ccdc_archive 'CCDC 735147' _audit_creation_date 2001-10-10T12:14:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1beta3 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic _chemical_name_systematic ; ? ; _chemical_formula_sum 'C19 H22 O3' _chemical_formula_weight 298.37 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6266(7) _cell_length_b 10.1023(10) _cell_length_c 12.3043(11) _cell_angle_alpha 90.769(8) _cell_angle_beta 96.613(10) _cell_angle_gamma 103.792(8) _cell_volume 793.91(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_special_details ; bscbs data was collected on a CAD 4 Enraf Nonius difractometer and due to time constraints the theta_max limit was 21.97 ; _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9755 _exptl_absorpt_correction_T_max 0.9836 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_number 2133 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 21.97 _diffrn_reflns_theta_full 21.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1926 _reflns_number_gt 1578 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement '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 _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_number_reflns 1926 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.133 _refine_ls_shift/su_mean 0.021 _refine_diff_density_max 0.157 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.037 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O3 O 0.2442(2) 0.47824(14) 0.12640(11) 0.0561(4) Uani 1 1 d . . . O2 O -0.0841(2) 0.20970(18) 0.13631(13) 0.0683(5) Uani 1 1 d . . . O1 O 0.2688(3) 0.36697(17) -0.02735(13) 0.0677(5) Uani 1 1 d . . . C6 C 0.2855(3) 0.25449(19) 0.14522(16) 0.0421(5) Uani 1 1 d . . . C5 C 0.4742(3) 0.3077(2) 0.23437(18) 0.0480(6) Uani 1 1 d . . . C4 C 0.4113(4) 0.3378(2) 0.34490(17) 0.0484(6) Uani 1 1 d . . . C3 C 0.2645(3) 0.2162(2) 0.39009(16) 0.0454(5) Uani 1 1 d . . . C2 C 0.3392(5) 0.0816(3) 0.3927(2) 0.0645(7) Uani 1 1 d . . . C1 C 0.1519(4) 0.0118(2) 0.3101(2) 0.0609(7) Uani 1 1 d . . . C9 C 0.1823(6) -0.0615(3) 0.2066(3) 0.0815(9) Uani 1 1 d . . . C8 C 0.3522(6) 0.0104(3) 0.1390(3) 0.0808(10) Uani 1 1 d . . . C7 C 0.3143(5) 0.1325(2) 0.0767(2) 0.0622(7) Uani 1 1 d . . . C11 C 0.0781(3) 0.20702(19) 0.19210(16) 0.0437(5) Uani 1 1 d . . . C10 C 0.0791(3) 0.1480(2) 0.30222(16) 0.0450(5) Uani 1 1 d . . . C12 C 0.2639(3) 0.3693(2) 0.06946(17) 0.0463(5) Uani 1 1 d . . . C13 C 0.2398(5) 0.6003(3) 0.0665(3) 0.0643(7) Uani 1 1 d . . . C14 C 0.2032(4) 0.2602(2) 0.49729(16) 0.0516(6) Uani 1 1 d . . . C15 C 0.0310(5) 0.3133(2) 0.5016(2) 0.0643(7) Uani 1 1 d . . . C16 C -0.0143(7) 0.3630(3) 0.5991(3) 0.0857(9) Uani 1 1 d . . . C17 C 0.1118(9) 0.3604(3) 0.6935(3) 0.1019(13) Uani 1 1 d . . . C18 C 0.2829(8) 0.3098(4) 0.6921(2) 0.1027(13) Uani 1 1 d . . . C19 C 0.3297(5) 0.2577(3) 0.5951(2) 0.0771(8) Uani 1 1 d . . . H10 H -0.057(3) 0.1414(19) 0.3244(15) 0.045(5) Uiso 1 1 d . . . H5A H 0.555(3) 0.235(2) 0.2402(17) 0.058(6) Uiso 1 1 d . . . H5B H 0.561(3) 0.388(2) 0.2084(16) 0.055(6) Uiso 1 1 d . . . H4A H 0.337(3) 0.417(2) 0.3390(16) 0.055(6) Uiso 1 1 d . . . H4B H 0.536(4) 0.364(2) 0.3962(18) 0.057(6) Uiso 1 1 d . . . H7A H 0.430(4) 0.167(2) 0.038(2) 0.070(7) Uiso 1 1 d . . . H7B H 0.187(5) 0.104(3) 0.024(2) 0.090(10) Uiso 1 1 d . . . H1 H 0.051(4) -0.051(2) 0.3470(18) 0.064(7) Uiso 1 1 d . . . H2A H 0.475(4) 0.088(2) 0.366(2) 0.075(8) Uiso 1 1 d . . . H2B H 0.344(4) 0.042(3) 0.462(2) 0.073(7) Uiso 1 1 d . . . H15 H -0.059(4) 0.319(2) 0.437(2) 0.065(7) Uiso 1 1 d . . . H8A H 0.366(4) -0.052(3) 0.084(2) 0.090(8) Uiso 1 1 d . . . H8B H 0.490(5) 0.037(3) 0.190(3) 0.102(11) Uiso 1 1 d . . . H19 H 0.453(4) 0.220(3) 0.589(2) 0.080(9) Uiso 1 1 d . . . H9A H 0.032(5) -0.080(3) 0.163(3) 0.103(11) Uiso 1 1 d . . . H9B H 0.215(4) -0.148(3) 0.230(2) 0.100(9) Uiso 1 1 d . . . H13B H 0.182(6) 0.575(4) -0.015(3) 0.133(12) Uiso 1 1 d . . . H13A H 0.374(6) 0.658(4) 0.076(3) 0.124(12) Uiso 1 1 d . . . H13C H 0.124(7) 0.635(4) 0.089(3) 0.145(14) Uiso 1 1 d . . . H18 H 0.374(6) 0.302(4) 0.751(3) 0.126(13) Uiso 1 1 d . . . H16 H -0.147(6) 0.401(4) 0.595(3) 0.127(13) Uiso 1 1 d . . . H17 H 0.085(5) 0.392(3) 0.766(3) 0.115(10) Uiso 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 O3 0.0771(11) 0.0467(9) 0.0513(9) 0.0105(7) 0.0160(7) 0.0240(7) O2 0.0458(10) 0.0936(13) 0.0614(10) 0.0149(9) 0.0004(8) 0.0109(8) O1 0.0886(12) 0.0802(12) 0.0421(10) 0.0096(8) 0.0147(8) 0.0323(9) C6 0.0444(12) 0.0402(11) 0.0428(11) 0.0023(9) 0.0101(9) 0.0105(9) C5 0.0420(13) 0.0469(13) 0.0573(14) 0.0103(11) 0.0108(10) 0.0123(11) C4 0.0438(13) 0.0509(13) 0.0456(12) 0.0033(10) -0.0010(11) 0.0048(11) C3 0.0475(12) 0.0450(12) 0.0431(12) 0.0062(9) 0.0027(9) 0.0110(10) C2 0.0738(18) 0.0597(15) 0.0693(17) 0.0243(13) 0.0167(15) 0.0297(13) C1 0.0788(18) 0.0382(12) 0.0657(15) 0.0067(11) 0.0246(14) 0.0064(12) C9 0.125(3) 0.0398(14) 0.086(2) 0.0049(14) 0.048(2) 0.0171(16) C8 0.121(3) 0.0452(15) 0.091(2) 0.0035(15) 0.054(2) 0.0284(16) C7 0.0782(19) 0.0485(14) 0.0658(16) -0.0001(12) 0.0352(16) 0.0144(13) C11 0.0436(13) 0.0426(12) 0.0437(12) -0.0025(9) 0.0050(10) 0.0086(10) C10 0.0415(13) 0.0456(12) 0.0465(12) 0.0005(9) 0.0104(10) 0.0053(10) C12 0.0444(13) 0.0519(13) 0.0439(13) 0.0023(10) 0.0095(10) 0.0123(10) C13 0.0670(18) 0.0513(14) 0.0787(19) 0.0232(13) 0.0126(15) 0.0194(14) C14 0.0631(15) 0.0446(12) 0.0399(12) 0.0067(9) 0.0057(11) -0.0010(11) C15 0.090(2) 0.0564(15) 0.0501(15) 0.0041(11) 0.0178(14) 0.0207(14) C16 0.128(3) 0.0584(17) 0.073(2) -0.0026(14) 0.048(2) 0.0109(17) C17 0.145(4) 0.073(2) 0.064(2) -0.0148(16) 0.045(2) -0.036(2) C18 0.122(3) 0.109(3) 0.0382(18) 0.0015(17) -0.003(2) -0.042(2) C19 0.076(2) 0.087(2) 0.0520(17) 0.0094(13) -0.0019(14) -0.0077(16) _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 O3 C12 1.337(2) . ? O3 C13 1.449(3) . ? O2 C11 1.213(2) . ? O1 C12 1.195(2) . ? C6 C12 1.520(3) . ? C6 C11 1.526(3) . ? C6 C7 1.545(3) . ? C6 C5 1.550(3) . ? C5 C4 1.515(3) . ? C4 C3 1.529(3) . ? C3 C14 1.516(3) . ? C3 C2 1.554(3) . ? C3 C10 1.557(3) . ? C2 C1 1.531(4) . ? C1 C9 1.522(3) . ? C1 C10 1.564(3) . ? C9 C8 1.526(4) . ? C8 C7 1.518(4) . ? C11 C10 1.487(3) . ? C14 C15 1.378(3) . ? C14 C19 1.390(3) . ? C15 C16 1.386(4) . ? C16 C17 1.355(5) . ? C17 C18 1.352(5) . ? C18 C19 1.394(5) . ? 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 C12 O3 C13 117.04(18) . . ? C12 C6 C11 107.22(16) . . ? C12 C6 C7 108.90(17) . . ? C11 C6 C7 106.80(18) . . ? C12 C6 C5 108.91(16) . . ? C11 C6 C5 113.17(16) . . ? C7 C6 C5 111.67(19) . . ? C4 C5 C6 113.58(18) . . ? C5 C4 C3 113.79(19) . . ? C14 C3 C4 109.11(17) . . ? C14 C3 C2 115.08(18) . . ? C4 C3 C2 115.42(19) . . ? C14 C3 C10 115.47(17) . . ? C4 C3 C10 111.32(16) . . ? C2 C3 C10 89.44(16) . . ? C1 C2 C3 90.89(18) . . ? C9 C1 C2 121.0(3) . . ? C9 C1 C10 120.0(2) . . ? C2 C1 C10 90.02(16) . . ? C1 C9 C8 118.3(2) . . ? C7 C8 C9 117.2(3) . . ? C8 C7 C6 116.8(2) . . ? O2 C11 C10 121.55(19) . . ? O2 C11 C6 119.53(18) . . ? C10 C11 C6 118.74(18) . . ? C11 C10 C3 116.69(17) . . ? C11 C10 C1 114.82(17) . . ? C3 C10 C1 89.55(16) . . ? O1 C12 O3 123.2(2) . . ? O1 C12 C6 126.11(19) . . ? O3 C12 C6 110.62(17) . . ? C15 C14 C19 117.2(3) . . ? C15 C14 C3 122.2(2) . . ? C19 C14 C3 120.4(2) . . ? C14 C15 C16 121.7(3) . . ? C17 C16 C15 120.2(4) . . ? C18 C17 C16 119.7(3) . . ? C17 C18 C19 121.0(3) . . ? C14 C19 C18 120.2(4) . . ? # Attachment 'bmcm3s.cif' data_bmcm3s _database_code_depnum_ccdc_archive 'CCDC 735148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 O3' _chemical_formula_weight 270.31 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.121(6) _cell_length_b 10.219(3) _cell_length_c 12.1028(18) _cell_angle_alpha 80.995(17) _cell_angle_beta 83.01(3) _cell_angle_gamma 82.18(5) _cell_volume 736.9(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; the heaviest atom in the complex is O and so it was considered unnecessary to perform absorption on the data. ? ; _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 'Enraf Nonius CAD 4' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2843 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.06 _reflns_number_total 2583 _reflns_number_gt 1387 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxtl _computing_publication_material Shelxtl _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^)+(0.0514P)^2^+0.0610P] 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_number_reflns 2583 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1294 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1273 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C4 C 0.1197(4) 0.8261(2) -0.0670(2) 0.0470(7) Uani 1 1 d . . . O1 O 0.3469(3) 0.90460(17) 0.16782(17) 0.0653(6) Uani 1 1 d . . . C2 C 0.2449(4) 0.8442(2) 0.1163(2) 0.0490(7) Uani 1 1 d . . . O3 O 0.4174(3) 0.59025(17) 0.1823(2) 0.0848(8) Uani 1 1 d . . . C3 C 0.2606(4) 0.8658(2) -0.0055(3) 0.0492(7) Uani 1 1 d . . . C12 C 0.1524(4) 0.8434(2) -0.1911(2) 0.0502(7) Uani 1 1 d . . . O2 O 0.1228(3) 0.51322(19) 0.1432(2) 0.0837(7) Uani 1 1 d . . . C5 C -0.0782(4) 0.7626(3) -0.0085(3) 0.0535(8) Uani 1 1 d . . . C6 C -0.1175(4) 0.7689(3) 0.1165(3) 0.0535(8) Uani 1 1 d . . . C10 C 0.2078(4) 0.6026(2) 0.1639(2) 0.0516(7) Uani 1 1 d . . . C1 C 0.0946(4) 0.7421(2) 0.1750(2) 0.0465(7) Uani 1 1 d . . . C13 C 0.3363(5) 0.8941(3) -0.2509(3) 0.0633(9) Uani 1 1 d . . . C17 C 0.0034(6) 0.8031(3) -0.2523(3) 0.0717(9) Uani 1 1 d . . . C7 C 0.0490(6) 0.7532(3) 0.3017(3) 0.0660(9) Uani 1 1 d . . . C14 C 0.3697(7) 0.9055(4) -0.3651(4) 0.0823(11) Uani 1 1 d . . . C16 C 0.0374(7) 0.8157(4) -0.3680(4) 0.0913(12) Uani 1 1 d . . . C15 C 0.2185(7) 0.8671(4) -0.4247(4) 0.0877(11) Uani 1 1 d . . . C11 C 0.5413(5) 0.4587(3) 0.1810(4) 0.1090(14) Uani 1 1 d . . . H11A H 0.4794 0.3974 0.2411 0.164 Uiso 1 1 calc R . . H11B H 0.6934 0.4630 0.1905 0.164 Uiso 1 1 calc R . . H11C H 0.5328 0.4289 0.1104 0.164 Uiso 1 1 calc R . . C8 C -0.0871(9) 0.6522(5) 0.3670(3) 0.0995(13) Uani 1 1 d . . . C9 C -0.2819(13) 0.6715(11) 0.4132(6) 0.157(3) Uani 1 1 d . . . H5A H -0.208(4) 0.808(2) -0.044(2) 0.062(8) Uiso 1 1 d . . . H6A H -0.217(4) 0.704(2) 0.1519(19) 0.052(7) Uiso 1 1 d . . . H6B H -0.192(4) 0.860(3) 0.130(2) 0.076(9) Uiso 1 1 d . . . H3 H 0.381(4) 0.912(2) -0.042(2) 0.056(7) Uiso 1 1 d . . . H5B H -0.062(4) 0.670(2) -0.0231(19) 0.053(7) Uiso 1 1 d . . . H17 H -0.132(5) 0.775(3) -0.217(2) 0.071(9) Uiso 1 1 d . . . H7B H -0.021(5) 0.840(3) 0.309(2) 0.074(9) Uiso 1 1 d . . . H7A H 0.201(7) 0.746(4) 0.332(3) 0.129(14) Uiso 1 1 d . . . H13 H 0.439(5) 0.924(3) -0.214(3) 0.085(10) Uiso 1 1 d . . . H15 H 0.240(5) 0.875(3) -0.505(3) 0.102(13) Uiso 1 1 d . . . H16 H -0.069(6) 0.786(3) -0.400(3) 0.098(12) Uiso 1 1 d . . . H14 H 0.492(6) 0.938(3) -0.404(3) 0.098(12) Uiso 1 1 d . . . H8 H -0.042(6) 0.558(4) 0.394(3) 0.112(15) Uiso 1 1 d . . . H9B H -0.356(9) 0.595(6) 0.453(5) 0.19(2) Uiso 1 1 d . . . H9A H -0.317(18) 0.759(10) 0.382(9) 0.39(7) Uiso 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 C4 0.0372(14) 0.0296(12) 0.075(2) -0.0106(12) -0.0081(14) -0.0025(11) O1 0.0631(12) 0.0570(11) 0.0870(15) -0.0219(10) -0.0207(11) -0.0215(10) C2 0.0369(14) 0.0345(14) 0.080(2) -0.0180(13) -0.0124(14) -0.0016(11) O3 0.0488(12) 0.0431(11) 0.168(2) -0.0227(12) -0.0320(13) 0.0023(9) C3 0.0380(15) 0.0361(14) 0.076(2) -0.0105(13) -0.0078(15) -0.0101(12) C12 0.0479(16) 0.0338(13) 0.070(2) -0.0076(13) -0.0109(15) -0.0047(12) O2 0.0750(14) 0.0463(11) 0.141(2) -0.0296(12) -0.0323(14) -0.0092(10) C5 0.0365(15) 0.0518(18) 0.076(2) -0.0092(15) -0.0139(15) -0.0098(13) C6 0.0378(15) 0.0464(17) 0.078(2) -0.0124(15) -0.0033(14) -0.0097(13) C10 0.0463(16) 0.0400(15) 0.0709(19) -0.0109(13) -0.0076(14) -0.0088(12) C1 0.0407(14) 0.0394(14) 0.0624(19) -0.0150(12) -0.0054(13) -0.0061(11) C13 0.063(2) 0.0569(18) 0.073(3) -0.0112(16) -0.0025(18) -0.0179(15) C17 0.063(2) 0.078(2) 0.079(3) -0.0143(18) -0.014(2) -0.0178(18) C7 0.066(2) 0.063(2) 0.073(2) -0.0215(17) -0.0039(18) -0.0109(18) C14 0.087(3) 0.083(2) 0.076(3) -0.011(2) 0.007(2) -0.022(2) C16 0.088(3) 0.107(3) 0.089(3) -0.021(2) -0.028(3) -0.025(2) C15 0.104(3) 0.090(3) 0.069(3) -0.014(2) -0.007(3) -0.011(2) C11 0.072(2) 0.0510(19) 0.205(4) -0.025(2) -0.036(3) 0.0174(17) C8 0.114(4) 0.118(4) 0.073(3) -0.026(3) 0.008(3) -0.040(3) C9 0.132(5) 0.237(9) 0.117(4) -0.044(5) 0.023(4) -0.089(6) _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 C4 C3 1.345(3) . ? C4 C12 1.477(4) . ? C4 C5 1.500(4) . ? O1 C2 1.216(3) . ? C2 C3 1.449(4) . ? C2 C1 1.520(3) . ? O3 C10 1.315(3) . ? O3 C11 1.452(3) . ? C12 C13 1.379(4) . ? C12 C17 1.383(4) . ? O2 C10 1.184(3) . ? C5 C6 1.513(4) . ? C6 C1 1.526(4) . ? C10 C1 1.516(3) . ? C1 C7 1.544(4) . ? C13 C14 1.361(5) . ? C17 C16 1.378(5) . ? C7 C8 1.484(5) . ? C14 C15 1.371(5) . ? C16 C15 1.355(5) . ? C8 C9 1.258(7) . ? 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 C3 C4 C12 122.1(3) . . ? C3 C4 C5 119.4(3) . . ? C12 C4 C5 118.5(2) . . ? O1 C2 C3 121.6(2) . . ? O1 C2 C1 122.4(3) . . ? C3 C2 C1 116.1(2) . . ? C10 O3 C11 116.9(2) . . ? C4 C3 C2 124.7(3) . . ? C13 C12 C17 117.0(3) . . ? C13 C12 C4 122.0(3) . . ? C17 C12 C4 120.9(3) . . ? C4 C5 C6 114.5(2) . . ? C5 C6 C1 113.5(2) . . ? O2 C10 O3 122.6(2) . . ? O2 C10 C1 125.9(2) . . ? O3 C10 C1 111.5(2) . . ? C10 C1 C2 109.6(2) . . ? C10 C1 C6 110.3(2) . . ? C2 C1 C6 106.8(2) . . ? C10 C1 C7 107.6(2) . . ? C2 C1 C7 110.5(2) . . ? C6 C1 C7 112.1(2) . . ? C14 C13 C12 121.8(4) . . ? C16 C17 C12 120.9(4) . . ? C8 C7 C1 114.2(3) . . ? C13 C14 C15 120.5(4) . . ? C15 C16 C17 120.9(4) . . ? C16 C15 C14 118.9(4) . . ? C9 C8 C7 127.6(7) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.112 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.033