# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Vishwakarma Singh' _publ_contact_author_email VKS@CHEM.IITB.AC.IN _publ_section_title ; Intra-molecular Cycloaddition in 6,6-Spiroepoxycyclohexa-2,4-dienone: Simple Aromatics to (+-) Platencin ; loop_ _publ_author_name 'Vishwakarma Singh' 'Varsha Bansal' 'Shaikh M Mobin' 'Bharat Chandra Sahu' # Attachment '5B.cif' data_CMPD5B _database_code_depnum_ccdc_archive 'CCDC 770204' #TrackingRef '5B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 O3' _chemical_formula_weight 220.26 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.448(3) _cell_length_b 6.840(3) _cell_length_c 13.210(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.22(3) _cell_angle_gamma 90.00 _cell_volume 1055.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 984 _cell_measurement_theta_min 3.1379 _cell_measurement_theta_max 32.4561 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_min 0.9695 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(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 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4908 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1844 _reflns_number_gt 1292 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0498P)^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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1844 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.92769(16) -0.0083(2) 0.06650(14) 0.0301(5) Uani 1 1 d . . . H101 H 0.9492 -0.0229 0.0133 0.045 Uiso 1 1 calc R . . O2 O 0.60516(16) 0.7417(2) -0.02395(14) 0.0278(5) Uani 1 1 d . . . O3 O 0.49137(14) 0.6923(2) 0.13332(13) 0.0229(4) Uani 1 1 d . . . C1 C 0.8425(2) 0.1432(3) 0.0434(2) 0.0217(6) Uani 1 1 d . . . H1 H 0.7751 0.1014 -0.0199 0.026 Uiso 1 1 calc R . . C2 C 0.8861(2) 0.3373(3) 0.0160(2) 0.0239(6) Uani 1 1 d . . . H2A H 0.9081 0.3202 -0.0487 0.029 Uiso 1 1 calc R . . H2B H 0.9554 0.3770 0.0766 0.029 Uiso 1 1 calc R . . C3 C 0.7960(2) 0.4988(3) -0.00538(19) 0.0220(6) Uani 1 1 d . . . H3A H 0.8293 0.6234 -0.0188 0.026 Uiso 1 1 calc R . . H3B H 0.7304 0.4661 -0.0711 0.026 Uiso 1 1 calc R . . C4 C 0.7537(2) 0.5251(3) 0.08863(18) 0.0170(6) Uani 1 1 d . . . C5 C 0.7107(2) 0.3234(3) 0.11985(19) 0.0166(5) Uani 1 1 d . . . H5 H 0.6427 0.2800 0.0576 0.020 Uiso 1 1 calc R . . C6 C 0.8037(2) 0.1687(3) 0.13943(19) 0.0187(6) Uani 1 1 d . . . H6A H 0.8702 0.2062 0.2032 0.022 Uiso 1 1 calc R . . H6B H 0.7742 0.0423 0.1555 0.022 Uiso 1 1 calc R . . C7 C 0.6722(2) 0.3531(3) 0.21841(18) 0.0212(6) Uani 1 1 d . . . H7A H 0.7194 0.2702 0.2789 0.025 Uiso 1 1 calc R . . H7B H 0.5914 0.3123 0.1995 0.025 Uiso 1 1 calc R . . C8 C 0.6849(2) 0.5704(4) 0.25410(18) 0.0204(6) Uani 1 1 d . . . H8 H 0.6624 0.5926 0.3189 0.024 Uiso 1 1 calc R . . C9 C 0.6134(2) 0.6912(3) 0.15813(19) 0.0179(6) Uani 1 1 d . . . C10 C 0.6519(2) 0.6624(3) 0.06209(19) 0.0185(6) Uani 1 1 d . . . C11 C 0.5544(2) 0.8733(3) 0.1685(2) 0.0231(6) Uani 1 1 d . . . H11A H 0.5650 0.9210 0.2421 0.028 Uiso 1 1 calc R . . H11B H 0.5460 0.9770 0.1140 0.028 Uiso 1 1 calc R . . C12 C 0.8064(2) 0.6315(3) 0.2733(2) 0.0236(6) Uani 1 1 d . . . H12 H 0.8549 0.6823 0.3405 0.028 Uiso 1 1 calc R . . C13 C 0.8408(2) 0.6092(3) 0.18977(19) 0.0216(6) Uani 1 1 d . . . H13 H 0.9158 0.6440 0.1931 0.026 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 0.0318(12) 0.0283(11) 0.0378(11) -0.0006(8) 0.0216(10) 0.0091(9) O2 0.0317(12) 0.0302(10) 0.0206(10) 0.0091(8) 0.0080(10) 0.0125(9) O3 0.0167(10) 0.0242(9) 0.0268(10) -0.0022(8) 0.0062(9) -0.0009(8) C1 0.0205(15) 0.0208(13) 0.0245(14) -0.0026(11) 0.0085(13) 0.0045(12) C2 0.0234(15) 0.0280(15) 0.0242(14) -0.0003(11) 0.0133(13) 0.0014(12) C3 0.0250(16) 0.0247(14) 0.0182(13) 0.0036(11) 0.0101(13) 0.0015(12) C4 0.0170(14) 0.0175(13) 0.0169(12) 0.0017(10) 0.0063(12) -0.0009(11) C5 0.0171(14) 0.0160(12) 0.0169(12) 0.0008(10) 0.0059(12) 0.0004(11) C6 0.0169(14) 0.0184(13) 0.0191(13) 0.0004(10) 0.0039(12) -0.0002(11) C7 0.0255(16) 0.0204(14) 0.0199(13) 0.0051(11) 0.0106(13) 0.0054(11) C8 0.0234(16) 0.0245(14) 0.0135(12) -0.0010(10) 0.0068(13) 0.0030(12) C9 0.0156(14) 0.0181(13) 0.0199(13) -0.0024(10) 0.0059(12) -0.0024(11) C10 0.0206(15) 0.0156(13) 0.0170(13) -0.0001(11) 0.0038(13) -0.0031(11) C11 0.0218(15) 0.0210(13) 0.0268(14) -0.0015(11) 0.0086(13) -0.0010(12) C12 0.0207(15) 0.0249(14) 0.0185(13) -0.0062(11) -0.0017(13) 0.0033(12) C13 0.0131(14) 0.0216(13) 0.0274(14) -0.0033(11) 0.0035(13) -0.0010(12) _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 C1 1.438(3) . ? O1 H101 0.8400 . ? O2 C10 1.212(3) . ? O3 C9 1.439(3) . ? O3 C11 1.454(3) . ? C1 C6 1.515(3) . ? C1 C2 1.525(3) . ? C1 H1 1.0000 . ? C2 C3 1.530(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C13 1.513(3) . ? C4 C10 1.518(3) . ? C4 C5 1.585(3) . ? C5 C6 1.523(3) . ? C5 C7 1.548(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.551(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C12 1.504(4) . ? C8 C9 1.517(3) . ? C8 H8 1.0000 . ? C9 C11 1.476(3) . ? C9 C10 1.516(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.324(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 C1 O1 H101 109.5 . . ? C9 O3 C11 61.37(15) . . ? O1 C1 C6 109.30(19) . . ? O1 C1 C2 112.4(2) . . ? C6 C1 C2 109.96(19) . . ? O1 C1 H1 108.4 . . ? C6 C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? C1 C2 C3 112.0(2) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 111.95(19) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C13 C4 C3 115.0(2) . . ? C13 C4 C10 104.77(19) . . ? C3 C4 C10 112.47(19) . . ? C13 C4 C5 107.73(19) . . ? C3 C4 C5 110.71(18) . . ? C10 C4 C5 105.57(19) . . ? C6 C5 C7 112.70(18) . . ? C6 C5 C4 110.12(19) . . ? C7 C5 C4 109.59(17) . . ? C6 C5 H5 108.1 . . ? C7 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? C1 C6 C5 112.41(19) . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C1 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? C5 C7 C8 110.66(18) . . ? C5 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C12 C8 C9 104.8(2) . . ? C12 C8 C7 107.9(2) . . ? C9 C8 C7 107.41(19) . . ? C12 C8 H8 112.1 . . ? C9 C8 H8 112.1 . . ? C7 C8 H8 112.1 . . ? O3 C9 C11 59.80(15) . . ? O3 C9 C10 115.1(2) . . ? C11 C9 C10 119.9(2) . . ? O3 C9 C8 117.5(2) . . ? C11 C9 C8 123.3(2) . . ? C10 C9 C8 111.4(2) . . ? O2 C10 C9 122.6(2) . . ? O2 C10 C4 125.9(2) . . ? C9 C10 C4 111.5(2) . . ? O3 C11 C9 58.83(14) . . ? O3 C11 H11A 117.9 . . ? C9 C11 H11A 117.9 . . ? O3 C11 H11B 117.9 . . ? C9 C11 H11B 117.9 . . ? H11A C11 H11B 115.0 . . ? C13 C12 C8 115.1(2) . . ? C13 C12 H12 122.5 . . ? C8 C12 H12 122.5 . . ? C12 C13 C4 116.1(2) . . ? C12 C13 H13 121.9 . . ? C4 C13 H13 121.9 . . ? 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 O1 C1 C2 C3 -178.44(19) . . . . ? C6 C1 C2 C3 -56.5(3) . . . . ? C1 C2 C3 C4 55.8(3) . . . . ? C2 C3 C4 C13 68.9(3) . . . . ? C2 C3 C4 C10 -171.3(2) . . . . ? C2 C3 C4 C5 -53.4(3) . . . . ? C13 C4 C5 C6 -73.0(2) . . . . ? C3 C4 C5 C6 53.5(3) . . . . ? C10 C4 C5 C6 175.43(18) . . . . ? C13 C4 C5 C7 51.5(2) . . . . ? C3 C4 C5 C7 178.0(2) . . . . ? C10 C4 C5 C7 -60.1(2) . . . . ? O1 C1 C6 C5 -178.44(19) . . . . ? C2 C1 C6 C5 57.8(3) . . . . ? C7 C5 C6 C1 -178.9(2) . . . . ? C4 C5 C6 C1 -56.2(3) . . . . ? C6 C5 C7 C8 124.4(2) . . . . ? C4 C5 C7 C8 1.4(3) . . . . ? C5 C7 C8 C12 -54.6(3) . . . . ? C5 C7 C8 C9 57.9(3) . . . . ? C11 O3 C9 C10 -111.4(2) . . . . ? C11 O3 C9 C8 114.4(2) . . . . ? C12 C8 C9 O3 -168.4(2) . . . . ? C7 C8 C9 O3 77.0(2) . . . . ? C12 C8 C9 C11 -98.1(3) . . . . ? C7 C8 C9 C11 147.3(2) . . . . ? C12 C8 C9 C10 55.8(2) . . . . ? C7 C8 C9 C10 -58.8(3) . . . . ? O3 C9 C10 O2 41.5(3) . . . . ? C11 C9 C10 O2 -26.7(4) . . . . ? C8 C9 C10 O2 178.4(2) . . . . ? O3 C9 C10 C4 -138.6(2) . . . . ? C11 C9 C10 C4 153.2(2) . . . . ? C8 C9 C10 C4 -1.6(3) . . . . ? C13 C4 C10 O2 127.2(3) . . . . ? C3 C4 C10 O2 1.7(3) . . . . ? C5 C4 C10 O2 -119.2(2) . . . . ? C13 C4 C10 C9 -52.7(2) . . . . ? C3 C4 C10 C9 -178.29(19) . . . . ? C5 C4 C10 C9 60.9(2) . . . . ? C10 C9 C11 O3 103.4(2) . . . . ? C8 C9 C11 O3 -104.8(2) . . . . ? C9 C8 C12 C13 -57.0(3) . . . . ? C7 C8 C12 C13 57.2(3) . . . . ? C8 C12 C13 C4 -0.4(3) . . . . ? C3 C4 C13 C12 -179.3(2) . . . . ? C10 C4 C13 C12 56.8(3) . . . . ? C5 C4 C13 C12 -55.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.260 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.049 # Attachment '18.cif' data_CMPD18 _database_code_depnum_ccdc_archive 'CCDC 770205' #TrackingRef '18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 O2' _chemical_formula_weight 204.26 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 'P b c a' 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' '-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 6.5326(19) _cell_length_b 16.022(7) _cell_length_c 21.032(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2201.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1190 _cell_measurement_theta_min 3.0909 _cell_measurement_theta_max 32.3919 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9349 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1932 _reflns_number_gt 1037 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0473P)^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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1932 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0871 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 0.827 _refine_ls_restrained_S_all 0.827 _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 0.1365(3) 0.33157(9) 0.06955(8) 0.1158(6) Uani 1 1 d . . . O2 O 0.55352(18) 0.12376(10) 0.25947(6) 0.0823(5) Uani 1 1 d . . . C1 C 0.2812(3) 0.28798(12) 0.08237(9) 0.0688(6) Uani 1 1 d . . . C2 C 0.4555(4) 0.31802(12) 0.12289(10) 0.0879(7) Uani 1 1 d . . . H2A H 0.4192 0.3710 0.1422 0.105 Uiso 1 1 calc R . . H2B H 0.5751 0.3269 0.0964 0.105 Uiso 1 1 calc R . . C3 C 0.5067(3) 0.25538(12) 0.17469(9) 0.0684(6) Uani 1 1 d . . . H3A H 0.3946 0.2537 0.2049 0.082 Uiso 1 1 calc R . . H3B H 0.6278 0.2742 0.1972 0.082 Uiso 1 1 calc R . . C4 C 0.5446(2) 0.16766(11) 0.14972(7) 0.0463(4) Uani 1 1 d . . . C5 C 0.3618(2) 0.13772(10) 0.10870(7) 0.0426(4) Uani 1 1 d . . . H5 H 0.2438 0.1309 0.1370 0.051 Uiso 1 1 calc R . . C6 C 0.3035(3) 0.20135(10) 0.05795(7) 0.0515(5) Uani 1 1 d . . . H6A H 0.4073 0.2010 0.0250 0.062 Uiso 1 1 calc R . . H6B H 0.1752 0.1844 0.0387 0.062 Uiso 1 1 calc R . . C7 C 0.7444(2) 0.15980(12) 0.11161(8) 0.0587(5) Uani 1 1 d . . . H7A H 0.7368 0.1952 0.0743 0.070 Uiso 1 1 calc R . . H7B H 0.8579 0.1789 0.1375 0.070 Uiso 1 1 calc R . . C8 C 0.7835(3) 0.06936(12) 0.09083(9) 0.0708(6) Uani 1 1 d . . . H8A H 0.8043 0.0673 0.0452 0.085 Uiso 1 1 calc R . . H8B H 0.9064 0.0485 0.1113 0.085 Uiso 1 1 calc R . . C9 C 0.6018(2) 0.01472(12) 0.10889(9) 0.0619(5) Uani 1 1 d . . . H9 H 0.6227 -0.0427 0.0943 0.074 Uiso 1 1 calc R . . C10 C 0.4091(3) 0.05189(11) 0.07917(9) 0.0598(5) Uani 1 1 d . . . H10A H 0.2944 0.0146 0.0861 0.072 Uiso 1 1 calc R . . H10B H 0.4285 0.0579 0.0337 0.072 Uiso 1 1 calc R . . C11 C 0.5803(2) 0.01756(13) 0.17948(10) 0.0643(5) Uani 1 1 d . . . C12 C 0.5741(3) -0.04718(16) 0.21827(12) 0.1072(9) Uani 1 1 d . . . H12A H 0.5566 -0.0390 0.2617 0.129 Uiso 1 1 calc R . . H12B H 0.5873 -0.1010 0.2021 0.129 Uiso 1 1 calc R . . C13 C 0.5598(2) 0.10465(14) 0.20348(8) 0.0572(5) 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 0.1521(14) 0.0778(11) 0.1173(13) -0.0110(10) -0.0476(11) 0.0504(11) O2 0.0638(7) 0.1437(14) 0.0395(7) 0.0113(8) -0.0052(6) -0.0011(9) C1 0.0923(15) 0.0557(13) 0.0584(13) 0.0017(11) -0.0115(11) 0.0133(12) C2 0.1241(18) 0.0573(14) 0.0824(15) -0.0136(13) -0.0131(14) -0.0048(14) C3 0.0740(12) 0.0752(14) 0.0561(12) -0.0134(12) -0.0126(9) -0.0050(11) C4 0.0431(8) 0.0582(11) 0.0376(9) -0.0024(9) -0.0018(8) -0.0044(9) C5 0.0399(8) 0.0505(11) 0.0373(9) 0.0001(9) 0.0002(7) -0.0007(8) C6 0.0587(10) 0.0562(12) 0.0394(10) -0.0002(10) -0.0060(8) 0.0032(9) C7 0.0459(9) 0.0792(14) 0.0509(11) 0.0081(10) -0.0003(8) -0.0103(10) C8 0.0568(11) 0.0876(16) 0.0681(13) 0.0048(12) 0.0127(10) 0.0084(11) C9 0.0571(11) 0.0549(12) 0.0739(13) 0.0044(11) 0.0018(10) 0.0089(9) C10 0.0598(10) 0.0526(12) 0.0670(12) -0.0041(10) -0.0103(9) -0.0014(9) C11 0.0463(10) 0.0728(14) 0.0737(13) 0.0284(13) 0.0011(10) 0.0063(10) C12 0.0898(15) 0.110(2) 0.121(2) 0.0572(18) 0.0107(15) 0.0192(14) C13 0.0338(8) 0.0961(16) 0.0415(10) 0.0131(11) -0.0030(8) -0.0033(10) _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 C1 1.206(2) . ? O2 C13 1.217(2) . ? C1 C6 1.487(2) . ? C1 C2 1.502(3) . ? C2 C3 1.519(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.521(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C13 1.519(2) . ? C4 C7 1.537(2) . ? C4 C5 1.549(2) . ? C5 C6 1.524(2) . ? C5 C10 1.540(2) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.535(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.523(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C11 1.492(3) . ? C9 C10 1.527(2) . ? C9 H9 0.9800 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.320(2) . ? C11 C13 1.490(3) . ? C12 H12A 0.9300 . ? C12 H12B 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 O1 C1 C6 122.68(19) . . ? O1 C1 C2 122.39(19) . . ? C6 C1 C2 114.90(17) . . ? C1 C2 C3 111.22(17) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 113.51(15) . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C13 C4 C3 111.58(14) . . ? C13 C4 C7 106.15(13) . . ? C3 C4 C7 113.22(15) . . ? C13 C4 C5 105.02(13) . . ? C3 C4 C5 110.67(13) . . ? C7 C4 C5 109.79(12) . . ? C6 C5 C10 111.41(13) . . ? C6 C5 C4 112.05(13) . . ? C10 C5 C4 110.26(12) . . ? C6 C5 H5 107.6 . . ? C10 C5 H5 107.6 . . ? C4 C5 H5 107.6 . . ? C1 C6 C5 114.00(14) . . ? C1 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C1 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C4 111.56(14) . . ? C8 C7 H7A 109.3 . . ? C4 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C4 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 109.99(14) . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C11 C9 C8 107.70(16) . . ? C11 C9 C10 108.54(14) . . ? C8 C9 C10 108.43(15) . . ? C11 C9 H9 110.7 . . ? C8 C9 H9 110.7 . . ? C10 C9 H9 110.7 . . ? C9 C10 C5 110.41(14) . . ? C9 C10 H10A 109.6 . . ? C5 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C5 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C13 121.6(2) . . ? C12 C11 C9 126.4(2) . . ? C13 C11 C9 111.98(16) . . ? C11 C12 H12A 120.0 . . ? C11 C12 H12B 120.0 . . ? H12A C12 H12B 120.0 . . ? O2 C13 C11 124.49(18) . . ? O2 C13 C4 123.41(19) . . ? C11 C13 C4 112.09(15) . . ? 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 O1 C1 C2 C3 131.5(2) . . . . ? C6 C1 C2 C3 -50.0(2) . . . . ? C1 C2 C3 C4 53.1(2) . . . . ? C2 C3 C4 C13 -170.49(15) . . . . ? C2 C3 C4 C7 69.83(19) . . . . ? C2 C3 C4 C5 -53.93(19) . . . . ? C13 C4 C5 C6 171.22(13) . . . . ? C3 C4 C5 C6 50.68(17) . . . . ? C7 C4 C5 C6 -75.03(17) . . . . ? C13 C4 C5 C10 -64.08(16) . . . . ? C3 C4 C5 C10 175.38(14) . . . . ? C7 C4 C5 C10 49.67(18) . . . . ? O1 C1 C6 C5 -132.6(2) . . . . ? C2 C1 C6 C5 49.0(2) . . . . ? C10 C5 C6 C1 -172.77(15) . . . . ? C4 C5 C6 C1 -48.71(19) . . . . ? C13 C4 C7 C8 53.72(18) . . . . ? C3 C4 C7 C8 176.47(14) . . . . ? C5 C4 C7 C8 -59.30(18) . . . . ? C4 C7 C8 C9 5.3(2) . . . . ? C7 C8 C9 C11 -61.17(19) . . . . ? C7 C8 C9 C10 56.1(2) . . . . ? C11 C9 C10 C5 51.1(2) . . . . ? C8 C9 C10 C5 -65.65(18) . . . . ? C6 C5 C10 C9 135.89(15) . . . . ? C4 C5 C10 C9 10.82(19) . . . . ? C8 C9 C11 C12 -125.9(2) . . . . ? C10 C9 C11 C12 116.9(2) . . . . ? C8 C9 C11 C13 55.72(17) . . . . ? C10 C9 C11 C13 -61.47(18) . . . . ? C12 C11 C13 O2 6.5(3) . . . . ? C9 C11 C13 O2 -175.04(15) . . . . ? C12 C11 C13 C4 -172.79(16) . . . . ? C9 C11 C13 C4 5.71(18) . . . . ? C3 C4 C13 O2 -3.8(2) . . . . ? C7 C4 C13 O2 119.97(16) . . . . ? C5 C4 C13 O2 -123.75(16) . . . . ? C3 C4 C13 C11 175.45(13) . . . . ? C7 C4 C13 C11 -60.77(17) . . . . ? C5 C4 C13 C11 55.51(16) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.129 _refine_diff_density_min -0.088 _refine_diff_density_rms 0.022