# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Sengodagounder Muthusamy' _publ_contact_author_address ; Organic chemistry Central salt & marine chemicals research institute GB Marg Bhavnagar 364002 INDIA ; _publ_contact_author_email MUTHU@CSMCRI.ORG _publ_section_title ; Highly regio-, chemo- and diastereoselective synthesis of epoxy-bridged spirocycles: A novel observation of reverse selectivity ; loop_ _publ_author_name 'Sengodagounder Muthusamy' 'Janagiraman Krishnamurthi' 'Munirathinam Nethaji' data_5a _database_code_depnum_ccdc_archive 'CCDC 266143' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'oxabridged spirocyclic six-membered-ring system' _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 O3' _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 MONOCLINIC _symmetry_space_group_name_H-M P21/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 12.644(7) _cell_length_b 9.115(5) _cell_length_c 14.429(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.578(10) _cell_angle_gamma 90.00 _cell_volume 1593.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 29.48 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'SMART APEX CCD' _diffrn_measurement_method OMEGA-PHI _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9685 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 29.48 _reflns_number_total 3982 _reflns_number_gt 3082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX CCD' _computing_cell_refinement 'SMART APEX CCD' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS -97' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'WINGX V164.04' _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^)+(0.1157P)^2^+0.2011P] 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 3982 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 C1 C 0.80579(11) 0.80020(15) 0.23188(11) 0.0313(3) Uani 1 1 d . . . C2 C 0.72456(14) 0.8024(2) 0.13236(13) 0.0430(4) Uani 1 1 d . . . C3 C 0.63987(15) 0.9255(2) 0.11791(15) 0.0535(5) Uani 1 1 d . . . C4 C 0.58463(15) 0.9275(3) 0.19854(17) 0.0606(6) Uani 1 1 d . . . C5 C 0.67102(14) 0.9436(2) 0.29601(16) 0.0500(4) Uani 1 1 d . . . C6 C 0.75457(12) 0.81433(16) 0.31709(12) 0.0349(3) Uani 1 1 d . . . C7 C 0.85713(12) 0.86560(16) 0.39599(11) 0.0342(3) Uani 1 1 d . . . C8 C 0.94349(11) 0.89401(15) 0.34317(10) 0.0296(3) Uani 1 1 d . . . C9 C 0.99235(11) 0.73993(15) 0.32621(11) 0.0301(3) Uani 1 1 d . . . C10 C 0.89176(13) 0.67677(16) 0.24844(12) 0.0361(3) Uani 1 1 d . . . O11 O 0.87618(8) 0.93125(10) 0.24851(7) 0.0322(3) Uani 1 1 d . . . C12 C 1.08821(12) 0.77278(16) 0.28516(11) 0.0324(3) Uani 1 1 d . . . C13 C 1.19965(12) 0.79238(15) 0.35532(12) 0.0342(3) Uani 1 1 d . . . C14 C 1.28641(14) 0.83566(19) 0.31953(16) 0.0478(4) Uani 1 1 d . . . C15 C 1.39131(15) 0.8549(2) 0.3820(2) 0.0634(6) Uani 1 1 d . . . C16 C 1.41005(16) 0.8290(2) 0.4793(2) 0.0661(6) Uani 1 1 d . . . C17 C 1.32554(16) 0.7850(2) 0.51509(16) 0.0544(5) Uani 1 1 d . . . C18 C 1.21851(13) 0.76664(17) 0.45408(12) 0.0385(4) Uani 1 1 d . . . C19 C 1.12606(15) 0.7194(2) 0.49362(12) 0.0446(4) Uani 1 1 d . . . C20 C 1.03303(13) 0.64513(18) 0.41725(12) 0.0379(3) Uani 1 1 d . . . C21 C 0.70405(18) 0.6758(2) 0.34631(17) 0.0541(5) Uani 1 1 d . . . O22 O 0.86695(10) 0.87971(15) 0.48103(9) 0.0509(3) Uani 1 1 d . . . O23 O 1.07493(11) 0.78733(16) 0.19915(9) 0.0521(4) Uani 1 1 d . . . H2A H 0.7656(17) 0.807(2) 0.0855(15) 0.047(5) Uiso 1 1 d . . . H2B H 0.6854(17) 0.703(2) 0.1231(15) 0.051(5) Uiso 1 1 d . . . H3A H 0.5839(17) 0.910(2) 0.0534(15) 0.055(6) Uiso 1 1 d . . . H3B H 0.6787(18) 1.024(3) 0.1173(16) 0.063(6) Uiso 1 1 d . . . H4A H 0.5395(19) 0.839(3) 0.1955(16) 0.062(6) Uiso 1 1 d . . . H4B H 0.529(2) 1.015(3) 0.1866(18) 0.082(8) Uiso 1 1 d . . . H5A H 0.6403(19) 0.950(3) 0.3503(17) 0.069(7) Uiso 1 1 d . . . H5B H 0.7101(16) 1.039(2) 0.2960(14) 0.050(5) Uiso 1 1 d . . . H8 H 0.9949(13) 0.9716(17) 0.3704(11) 0.029(4) Uiso 1 1 d . . . H10A H 0.9111(16) 0.654(2) 0.1870(15) 0.046(5) Uiso 1 1 d . . . H10B H 0.8697(16) 0.584(2) 0.2714(14) 0.050(5) Uiso 1 1 d . . . H14 H 1.2710(18) 0.849(3) 0.2489(18) 0.064(6) Uiso 1 1 d . . . H15 H 1.451(3) 0.884(3) 0.357(2) 0.101(9) Uiso 1 1 d . . . H16 H 1.481(2) 0.844(3) 0.5242(18) 0.073(7) Uiso 1 1 d . . . H17 H 1.342(2) 0.765(3) 0.5818(19) 0.069(7) Uiso 1 1 d . . . H19A H 1.1583(18) 0.655(3) 0.5517(17) 0.064(6) Uiso 1 1 d . . . H19B H 1.0978(18) 0.805(2) 0.5199(16) 0.055(6) Uiso 1 1 d . . . H20A H 0.9717(16) 0.626(2) 0.4431(13) 0.042(5) Uiso 1 1 d . . . H20B H 1.0584(15) 0.549(2) 0.3991(13) 0.045(5) Uiso 1 1 d . . . H21A H 0.758(2) 0.594(3) 0.3684(17) 0.069(7) Uiso 1 1 d . . . H21B H 0.649(2) 0.635(3) 0.293(2) 0.080(7) Uiso 1 1 d . . . H21C H 0.672(3) 0.699(3) 0.401(2) 0.091(8) 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 C1 0.0310(6) 0.0291(6) 0.0343(8) -0.0039(5) 0.0101(6) -0.0028(5) C2 0.0378(8) 0.0496(9) 0.0384(9) -0.0048(7) 0.0057(7) -0.0018(7) C3 0.0406(9) 0.0535(11) 0.0577(12) 0.0031(9) 0.0001(8) 0.0035(7) C4 0.0342(9) 0.0667(13) 0.0767(15) -0.0086(11) 0.0089(9) 0.0092(8) C5 0.0380(8) 0.0533(10) 0.0636(12) -0.0133(9) 0.0223(8) 0.0032(7) C6 0.0316(7) 0.0372(7) 0.0392(8) -0.0064(6) 0.0153(6) -0.0068(5) C7 0.0372(7) 0.0322(7) 0.0370(8) -0.0048(6) 0.0165(6) -0.0022(5) C8 0.0308(6) 0.0287(6) 0.0307(7) -0.0030(5) 0.0110(5) -0.0039(5) C9 0.0324(7) 0.0302(6) 0.0299(7) -0.0005(5) 0.0122(5) 0.0010(5) C10 0.0348(7) 0.0325(7) 0.0401(9) -0.0093(6) 0.0094(6) -0.0008(5) O11 0.0328(5) 0.0290(5) 0.0351(6) 0.0014(4) 0.0104(4) -0.0025(4) C12 0.0357(7) 0.0344(7) 0.0299(7) 0.0025(6) 0.0140(6) 0.0047(5) C13 0.0329(7) 0.0325(7) 0.0389(8) 0.0011(6) 0.0130(6) 0.0044(5) C14 0.0376(8) 0.0470(9) 0.0640(12) 0.0075(8) 0.0228(8) 0.0046(7) C15 0.0355(9) 0.0563(11) 0.1003(19) 0.0049(11) 0.0227(10) -0.0006(8) C16 0.0364(9) 0.0589(12) 0.0907(18) -0.0096(11) -0.0017(10) -0.0005(8) C17 0.0470(10) 0.0536(10) 0.0521(12) -0.0098(9) -0.0025(8) 0.0068(8) C18 0.0408(8) 0.0345(7) 0.0383(8) -0.0034(6) 0.0082(6) 0.0057(6) C19 0.0502(9) 0.0557(10) 0.0276(8) 0.0031(7) 0.0108(7) 0.0077(8) C20 0.0427(8) 0.0370(8) 0.0371(9) 0.0082(6) 0.0163(7) 0.0023(6) C21 0.0561(11) 0.0544(11) 0.0578(12) -0.0026(9) 0.0258(10) -0.0224(9) O22 0.0536(7) 0.0679(8) 0.0374(7) -0.0122(6) 0.0231(5) -0.0090(6) O23 0.0500(7) 0.0792(9) 0.0315(7) 0.0057(6) 0.0188(5) 0.0034(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 C1 O11 1.4678(17) . ? C1 C2 1.509(2) . ? C1 C10 1.535(2) . ? C1 C6 1.550(2) . ? C2 C3 1.524(3) . ? C3 C4 1.518(3) . ? C4 C5 1.522(3) . ? C5 C6 1.554(2) . ? C6 C21 1.527(2) . ? C6 C7 1.534(2) . ? C7 O22 1.205(2) . ? C7 C8 1.522(2) . ? C8 O11 1.4288(18) . ? C8 C9 1.581(2) . ? C9 C12 1.523(2) . ? C9 C20 1.533(2) . ? C9 C10 1.547(2) . ? C12 O23 1.211(2) . ? C12 C13 1.493(2) . ? C13 C18 1.396(2) . ? C13 C14 1.396(2) . ? C14 C15 1.386(3) . ? C15 C16 1.375(4) . ? C16 C17 1.373(3) . ? C17 C18 1.398(2) . ? C18 C19 1.502(3) . ? C19 C20 1.522(2) . ? 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 O11 C1 C2 111.18(12) . . ? O11 C1 C10 101.63(11) . . ? C2 C1 C10 114.67(13) . . ? O11 C1 C6 100.01(11) . . ? C2 C1 C6 115.40(13) . . ? C10 C1 C6 112.03(13) . . ? C1 C2 C3 113.64(15) . . ? C4 C3 C2 111.28(17) . . ? C3 C4 C5 110.09(16) . . ? C4 C5 C6 112.10(15) . . ? C21 C6 C7 112.24(15) . . ? C21 C6 C1 116.91(14) . . ? C7 C6 C1 99.09(12) . . ? C21 C6 C5 111.49(15) . . ? C7 C6 C5 107.33(13) . . ? C1 C6 C5 108.81(14) . . ? O22 C7 C8 127.74(14) . . ? O22 C7 C6 127.46(14) . . ? C8 C7 C6 104.81(13) . . ? O11 C8 C7 101.68(11) . . ? O11 C8 C9 102.44(11) . . ? C7 C8 C9 107.11(11) . . ? C12 C9 C20 109.53(12) . . ? C12 C9 C10 111.83(13) . . ? C20 C9 C10 114.65(13) . . ? C12 C9 C8 105.96(11) . . ? C20 C9 C8 114.72(13) . . ? C10 C9 C8 99.56(11) . . ? C1 C10 C9 103.84(12) . . ? C8 O11 C1 97.53(10) . . ? O23 C12 C13 120.67(14) . . ? O23 C12 C9 121.80(14) . . ? C13 C12 C9 117.50(13) . . ? C18 C13 C14 120.12(16) . . ? C18 C13 C12 121.70(14) . . ? C14 C13 C12 118.17(16) . . ? C15 C14 C13 120.2(2) . . ? C16 C15 C14 119.8(2) . . ? C17 C16 C15 120.56(19) . . ? C16 C17 C18 121.0(2) . . ? C13 C18 C17 118.39(17) . . ? C13 C18 C19 120.73(14) . . ? C17 C18 C19 120.88(17) . . ? C18 C19 C20 112.14(14) . . ? C19 C20 C9 111.75(14) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 29.48 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.229 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.060 #===END data_10a _database_code_depnum_ccdc_archive 'CCDC 266144' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'oxabridged spirocyclic seven-membered-ring system' _chemical_melting_point ? _chemical_formula_moiety 'C21 H18 O3' _chemical_formula_sum 'C21 H18 O3' _chemical_formula_weight 318.35 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 6.265(4) _cell_length_b 20.618(13) _cell_length_c 25.042(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.062(11) _cell_angle_gamma 90.00 _cell_volume 3210(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 26.02 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'SMART APEX CCD' _diffrn_measurement_method OMEGA-PHI _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12164 _diffrn_reflns_av_R_equivalents 0.1213 _diffrn_reflns_av_sigmaI/netI 0.0822 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.02 _reflns_number_total 5769 _reflns_number_gt 4770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART APEX CCD' _computing_cell_refinement 'SMART APEX CCD' _computing_data_reduction ?'SAINT' _computing_structure_solution 'SHELXS 97' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'WINGX V1.64.04' _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^)+(0.0719P)^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' _refine_ls_abs_structure_Flack 0.1(11) _refine_ls_number_reflns 5769 _refine_ls_number_parameters 577 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.002 _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 C1 C 0.2977(4) 0.45224(13) 0.37559(10) 0.0394(5) Uani 1 1 d . . . C2 C 0.1328(5) 0.41646(13) 0.40603(12) 0.0450(6) Uani 1 1 d . . . C3 C 0.1448(6) 0.34221(16) 0.40298(17) 0.0613(8) Uani 1 1 d . . . C4 C 0.3652(6) 0.31710(15) 0.39707(14) 0.0624(9) Uani 1 1 d . . . C5 C 0.4969(5) 0.36165(15) 0.36607(13) 0.0550(8) Uani 1 1 d . . . C6 C 0.2742(4) 0.44153(14) 0.31256(11) 0.0437(6) Uani 1 1 d . . . C7 C 0.3779(6) 0.37328(16) 0.30931(14) 0.0521(7) Uani 1 1 d . . . O8 O 0.5065(3) 0.42442(10) 0.39140(8) 0.0493(5) Uani 1 1 d . . . C9 C 0.0442(4) 0.44155(15) 0.28322(10) 0.0437(6) Uani 1 1 d . . . C10 C 0.0366(5) 0.48775(15) 0.23834(10) 0.0477(7) Uani 1 1 d . . . C11 C -0.1368(6) 0.5004(2) 0.19824(13) 0.0622(9) Uani 1 1 d . . . C12 C -0.1054(7) 0.5461(2) 0.15939(15) 0.0812(12) Uani 1 1 d . . . C13 C 0.0925(8) 0.5770(2) 0.16004(17) 0.0838(12) Uani 1 1 d . . . C14 C 0.2643(7) 0.5638(2) 0.19853(15) 0.0685(9) Uani 1 1 d . . . C15 C 0.2349(5) 0.51757(15) 0.23888(12) 0.0493(7) Uani 1 1 d . . . C16 C 0.3964(5) 0.49413(19) 0.28396(13) 0.0542(7) Uani 1 1 d . . . O17 O 0.4309(6) 0.26424(13) 0.41378(15) 0.1006(10) Uani 1 1 d . . . O18 O -0.1036(3) 0.40770(12) 0.29372(9) 0.0601(6) Uani 1 1 d . . . C19 C 0.3039(4) 0.52317(13) 0.39214(10) 0.0408(6) Uani 1 1 d . . . C20 C 0.1179(5) 0.56009(15) 0.38338(13) 0.0523(7) Uani 1 1 d . . . C21 C 0.1172(6) 0.62503(16) 0.39941(14) 0.0596(8) Uani 1 1 d . . . C22 C 0.3022(6) 0.65276(16) 0.42402(13) 0.0586(8) Uani 1 1 d . . . C23 C 0.4882(6) 0.61703(16) 0.43247(13) 0.0608(8) Uani 1 1 d . . . C24 C 0.4877(5) 0.55217(15) 0.41677(12) 0.0508(7) Uani 1 1 d . . . C1A C 0.6478(4) 0.20259(13) 0.57554(10) 0.0387(5) Uani 1 1 d . . . C2A C 0.4526(5) 0.16669(14) 0.54496(12) 0.0457(6) Uani 1 1 d . . . C3A C 0.4670(6) 0.09207(15) 0.54830(16) 0.0617(8) Uani 1 1 d . . . C4A C 0.6930(6) 0.06694(15) 0.55382(14) 0.0627(9) Uani 1 1 d . . . C5A C 0.8565(5) 0.11192(15) 0.58545(14) 0.0558(8) Uani 1 1 d . . . C6A C 0.6878(4) 0.19169(14) 0.63844(11) 0.0422(6) Uani 1 1 d . . . C7A C 0.7953(5) 0.12325(15) 0.64178(13) 0.0508(7) Uani 1 1 d . . . O8A O 0.8403(3) 0.17421(10) 0.55948(8) 0.0494(5) Uani 1 1 d . . . C9A C 0.4867(4) 0.19141(15) 0.66820(10) 0.0441(6) Uani 1 1 d . . . C10A C 0.5244(4) 0.23785(15) 0.71315(10) 0.0476(7) Uani 1 1 d . . . C11A C 0.3911(6) 0.2509(2) 0.75272(13) 0.0623(9) Uani 1 1 d . . . C12A C 0.4603(8) 0.2961(2) 0.79179(16) 0.0831(13) Uani 1 1 d . . . C13A C 0.6590(8) 0.3266(2) 0.79105(17) 0.0849(13) Uani 1 1 d . . . C14A C 0.7914(7) 0.31327(19) 0.75238(15) 0.0692(9) Uani 1 1 d . . . C15A C 0.7225(5) 0.26778(14) 0.71268(12) 0.0486(7) Uani 1 1 d . . . C16A C 0.8376(5) 0.24444(19) 0.66763(13) 0.0542(8) Uani 1 1 d . . . O17A O 0.7437(6) 0.01462(13) 0.53769(14) 0.1002(10) Uani 1 1 d . . . O18A O 0.3285(3) 0.15762(12) 0.65750(9) 0.0608(6) Uani 1 1 d . . . C19A C 0.6363(4) 0.27314(13) 0.55887(10) 0.0408(6) Uani 1 1 d . . . C20A C 0.7976(5) 0.30226(15) 0.53416(12) 0.0509(7) Uani 1 1 d . . . C21A C 0.7812(6) 0.36687(16) 0.51880(13) 0.0606(8) Uani 1 1 d . . . C22A C 0.6047(6) 0.40276(15) 0.52715(13) 0.0578(8) Uani 1 1 d . . . C23A C 0.4432(6) 0.37509(16) 0.55164(14) 0.0581(8) Uani 1 1 d . . . C24A C 0.4586(5) 0.30979(15) 0.56775(13) 0.0517(7) Uani 1 1 d . . . H2A H 0.178(4) 0.4299(16) 0.4452(13) 0.046(8) Uiso 1 1 d . . . H2B H -0.018(4) 0.4282(13) 0.3920(11) 0.028(6) Uiso 1 1 d . . . H3A H 0.058(6) 0.330(2) 0.3728(17) 0.068(11) Uiso 1 1 d . . . H3B H 0.082(8) 0.322(3) 0.437(2) 0.102(14) Uiso 1 1 d . . . H5 H 0.643(5) 0.3465(15) 0.3682(12) 0.043(7) Uiso 1 1 d . . . H7A H 0.261(5) 0.3436(17) 0.3019(13) 0.051(8) Uiso 1 1 d . . . H7B H 0.474(6) 0.3757(18) 0.2908(15) 0.060(10) Uiso 1 1 d . . . H11 H -0.286(6) 0.4751(19) 0.1994(15) 0.068(10) Uiso 1 1 d . . . H12 H -0.243(7) 0.549(2) 0.1331(19) 0.083(12) Uiso 1 1 d . . . H13 H 0.093(10) 0.613(3) 0.125(3) 0.14(2) Uiso 1 1 d . . . H14 H 0.406(5) 0.5821(15) 0.1973(13) 0.043(7) Uiso 1 1 d . . . H16B H 0.528(6) 0.4779(18) 0.2691(15) 0.065(9) Uiso 1 1 d . . . H16A H 0.437(6) 0.525(2) 0.3093(18) 0.071(11) Uiso 1 1 d . . . H20 H -0.012(6) 0.5412(19) 0.3685(16) 0.067(10) Uiso 1 1 d . . . H21 H -0.014(6) 0.646(2) 0.3949(15) 0.069(10) Uiso 1 1 d . . . H22 H 0.306(5) 0.6977(19) 0.4362(14) 0.064(10) Uiso 1 1 d . . . H23 H 0.624(8) 0.631(2) 0.4459(19) 0.086(12) Uiso 1 1 d . . . H24 H 0.611(5) 0.5318(15) 0.4228(11) 0.039(7) Uiso 1 1 d . . . H2' H 0.310(5) 0.1767(14) 0.5556(11) 0.033(7) Uiso 1 1 d . . . H2'' H 0.454(4) 0.1781(14) 0.5065(13) 0.037(7) Uiso 1 1 d . . . H3' H 0.370(7) 0.071(2) 0.510(2) 0.094(13) Uiso 1 1 d . . . H3'' H 0.415(5) 0.0743(19) 0.5812(15) 0.061(9) Uiso 1 1 d . . . H5' H 1.002(6) 0.0991(18) 0.5923(15) 0.061(9) Uiso 1 1 d . . . H7' H 0.692(5) 0.0915(19) 0.6502(14) 0.057(9) Uiso 1 1 d . . . H7'' H 0.931(6) 0.1270(17) 0.6713(16) 0.067(10) Uiso 1 1 d . . . H11' H 0.256(6) 0.2296(18) 0.7546(14) 0.057(9) Uiso 1 1 d . . . H12' H 0.357(7) 0.301(2) 0.8173(18) 0.082(12) Uiso 1 1 d . . . H13' H 0.698(7) 0.359(2) 0.8171(19) 0.089(13) Uiso 1 1 d . . . H14' H 0.930(6) 0.3289(17) 0.7583(15) 0.057(9) Uiso 1 1 d . . . H161 H 0.987(6) 0.2285(16) 0.6772(13) 0.056(9) Uiso 1 1 d . . . H162 H 0.866(5) 0.274(2) 0.6434(17) 0.064(10) Uiso 1 1 d . . . H20' H 0.925(6) 0.2782(17) 0.5275(13) 0.054(8) Uiso 1 1 d . . . H21' H 0.881(6) 0.390(2) 0.5048(16) 0.067(10) Uiso 1 1 d . . . H22' H 0.588(5) 0.4461(17) 0.5156(13) 0.051(8) Uiso 1 1 d . . . H23' H 0.299(6) 0.3950(18) 0.5529(14) 0.059(9) Uiso 1 1 d . . . H24' H 0.329(7) 0.289(2) 0.5849(18) 0.081(12) 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 C1 0.0481(13) 0.0336(13) 0.0351(13) -0.0021(11) -0.0006(10) 0.0061(10) C2 0.0604(17) 0.0339(14) 0.0409(15) 0.0016(12) 0.0072(12) 0.0047(12) C3 0.088(2) 0.0347(16) 0.063(2) 0.0044(15) 0.0141(18) 0.0008(15) C4 0.087(2) 0.0307(15) 0.064(2) -0.0074(13) -0.0093(17) 0.0142(15) C5 0.0509(16) 0.0432(16) 0.068(2) -0.0138(14) -0.0036(13) 0.0174(13) C6 0.0444(13) 0.0456(15) 0.0412(14) -0.0058(12) 0.0059(10) 0.0038(11) C7 0.0471(16) 0.0533(18) 0.0556(18) -0.0162(14) 0.0055(13) 0.0073(14) O8 0.0540(11) 0.0376(11) 0.0521(12) -0.0085(8) -0.0107(8) 0.0115(8) C9 0.0498(14) 0.0476(15) 0.0334(13) -0.0065(11) 0.0040(11) 0.0048(12) C10 0.0595(16) 0.0517(17) 0.0324(14) -0.0031(12) 0.0077(11) 0.0161(13) C11 0.0646(19) 0.082(2) 0.0386(16) -0.0031(16) 0.0009(13) 0.0229(18) C12 0.091(3) 0.109(3) 0.0437(19) 0.017(2) 0.0093(18) 0.041(2) C13 0.107(3) 0.088(3) 0.060(2) 0.024(2) 0.026(2) 0.038(3) C14 0.086(3) 0.064(2) 0.061(2) 0.0116(17) 0.0264(18) 0.0099(19) C15 0.0636(17) 0.0472(16) 0.0392(14) -0.0048(12) 0.0145(12) 0.0089(14) C16 0.0542(17) 0.064(2) 0.0447(17) -0.0018(15) 0.0093(13) -0.0053(15) O17 0.136(3) 0.0364(14) 0.121(2) 0.0030(15) -0.016(2) 0.0260(14) O18 0.0504(11) 0.0701(15) 0.0580(13) 0.0067(11) -0.0006(9) -0.0080(11) C19 0.0538(14) 0.0345(14) 0.0342(13) 0.0019(11) 0.0051(10) 0.0041(11) C20 0.0582(17) 0.0357(15) 0.0609(19) -0.0036(13) -0.0003(14) 0.0064(13) C21 0.071(2) 0.0417(17) 0.065(2) -0.0021(15) 0.0051(15) 0.0175(15) C22 0.090(2) 0.0370(16) 0.0476(17) -0.0023(14) 0.0053(15) 0.0021(16) C23 0.077(2) 0.0466(18) 0.0543(18) -0.0052(15) -0.0076(15) -0.0105(16) C24 0.0578(17) 0.0432(16) 0.0493(17) -0.0032(13) -0.0018(13) 0.0034(13) C1A 0.0467(13) 0.0335(13) 0.0359(13) -0.0007(11) 0.0052(10) 0.0067(10) C2A 0.0610(17) 0.0358(15) 0.0390(16) -0.0017(12) 0.0002(12) 0.0018(12) C3A 0.083(2) 0.0335(16) 0.067(2) -0.0050(15) 0.0020(17) -0.0005(15) C4A 0.096(2) 0.0312(15) 0.064(2) 0.0048(14) 0.0214(17) 0.0141(15) C5A 0.0609(18) 0.0408(16) 0.068(2) 0.0138(14) 0.0184(15) 0.0207(13) C6A 0.0460(13) 0.0449(15) 0.0346(13) 0.0032(11) 0.0012(10) 0.0059(11) C7A 0.0535(15) 0.0467(16) 0.0518(16) 0.0140(13) 0.0046(13) 0.0120(14) O8A 0.0603(11) 0.0381(11) 0.0528(12) 0.0062(9) 0.0186(9) 0.0147(9) C9A 0.0444(13) 0.0519(16) 0.0352(14) 0.0049(12) 0.0014(10) 0.0066(12) C10A 0.0573(16) 0.0515(17) 0.0323(14) 0.0030(12) -0.0007(11) 0.0165(13) C11A 0.065(2) 0.079(2) 0.0416(17) 0.0006(16) 0.0044(14) 0.0208(18) C12A 0.090(3) 0.111(3) 0.046(2) -0.021(2) -0.0003(18) 0.037(2) C13A 0.100(3) 0.088(3) 0.060(2) -0.029(2) -0.016(2) 0.034(3) C14A 0.079(3) 0.065(2) 0.056(2) -0.0097(17) -0.0183(17) 0.0082(18) C15A 0.0569(16) 0.0442(15) 0.0404(14) 0.0022(12) -0.0105(12) 0.0100(13) C16A 0.0533(17) 0.066(2) 0.0413(16) 0.0006(15) -0.0004(12) -0.0087(15) O17A 0.156(3) 0.0380(14) 0.113(2) -0.0103(15) 0.041(2) 0.0264(16) O18A 0.0515(11) 0.0692(15) 0.0627(13) -0.0075(11) 0.0108(9) -0.0099(11) C19A 0.0540(14) 0.0341(14) 0.0329(13) -0.0015(10) 0.0000(10) 0.0034(11) C20A 0.0634(17) 0.0430(16) 0.0475(16) 0.0004(13) 0.0120(13) 0.0015(14) C21A 0.086(2) 0.0446(17) 0.0538(19) 0.0075(15) 0.0192(16) -0.0084(17) C22A 0.091(2) 0.0318(15) 0.0486(17) 0.0016(13) 0.0022(15) 0.0017(15) C23A 0.072(2) 0.0395(16) 0.0626(19) 0.0025(14) 0.0093(15) 0.0132(15) C24A 0.0617(17) 0.0369(15) 0.0570(18) 0.0027(13) 0.0095(14) 0.0093(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 O8 1.439(3) . ? C1 C19 1.519(4) . ? C1 C2 1.545(4) . ? C1 C6 1.583(4) . ? C2 C3 1.535(4) . ? C3 C4 1.499(5) . ? C4 O17 1.221(4) . ? C4 C5 1.511(5) . ? C5 O8 1.439(4) . ? C5 C7 1.540(5) . ? C6 C9 1.535(4) . ? C6 C16 1.552(5) . ? C6 C7 1.556(4) . ? C9 O18 1.214(4) . ? C9 C10 1.469(4) . ? C10 C15 1.385(5) . ? C10 C11 1.410(4) . ? C11 C12 1.385(6) . ? C12 C13 1.392(7) . ? C13 C14 1.381(6) . ? C14 C15 1.418(5) . ? C15 C16 1.501(5) . ? C19 C24 1.375(4) . ? C19 C20 1.386(4) . ? C20 C21 1.398(5) . ? C21 C22 1.369(5) . ? C22 C23 1.373(5) . ? C23 C24 1.394(5) . ? C1A O8A 1.442(3) . ? C1A C19A 1.513(4) . ? C1A C2A 1.549(4) . ? C1A C6A 1.580(4) . ? C2A C3A 1.543(4) . ? C3A C4A 1.498(5) . ? C4A O17A 1.208(4) . ? C4A C5A 1.529(5) . ? C5A O8A 1.437(4) . ? C5A C7A 1.525(5) . ? C6A C9A 1.541(4) . ? C6A C16A 1.559(4) . ? C6A C7A 1.561(4) . ? C9A O18A 1.214(4) . ? C9A C10A 1.475(4) . ? C10A C15A 1.387(5) . ? C10A C11A 1.398(5) . ? C11A C12A 1.381(6) . ? C12A C13A 1.397(7) . ? C13A C14A 1.378(6) . ? C14A C15A 1.396(5) . ? C15A C16A 1.492(5) . ? C19A C20A 1.385(4) . ? C19A C24A 1.386(4) . ? C20A C21A 1.387(5) . ? C21A C22A 1.368(5) . ? C22A C23A 1.370(5) . ? C23A C24A 1.405(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 O8 C1 C19 108.5(2) . . ? O8 C1 C2 108.3(2) . . ? C19 C1 C2 108.7(2) . . ? O8 C1 C6 100.9(2) . . ? C19 C1 C6 113.7(2) . . ? C2 C1 C6 116.1(2) . . ? C3 C2 C1 114.3(2) . . ? C4 C3 C2 113.6(3) . . ? O17 C4 C3 123.4(4) . . ? O17 C4 C5 122.4(4) . . ? C3 C4 C5 114.1(3) . . ? O8 C5 C4 108.4(3) . . ? O8 C5 C7 104.8(2) . . ? C4 C5 C7 109.6(3) . . ? C9 C6 C16 105.4(2) . . ? C9 C6 C7 110.4(2) . . ? C16 C6 C7 112.0(3) . . ? C9 C6 C1 116.4(2) . . ? C16 C6 C1 111.8(2) . . ? C7 C6 C1 101.0(2) . . ? C5 C7 C6 104.5(2) . . ? C1 O8 C5 104.5(2) . . ? O18 C9 C10 125.8(3) . . ? O18 C9 C6 126.3(3) . . ? C10 C9 C6 107.8(2) . . ? C15 C10 C11 122.4(3) . . ? C15 C10 C9 109.6(2) . . ? C11 C10 C9 127.9(3) . . ? C12 C11 C10 117.6(4) . . ? C11 C12 C13 120.4(3) . . ? C14 C13 C12 122.3(4) . . ? C13 C14 C15 118.1(4) . . ? C10 C15 C14 119.1(3) . . ? C10 C15 C16 112.7(3) . . ? C14 C15 C16 128.2(3) . . ? C15 C16 C6 104.3(3) . . ? C24 C19 C20 118.3(3) . . ? C24 C19 C1 122.2(2) . . ? C20 C19 C1 119.5(2) . . ? C19 C20 C21 120.8(3) . . ? C22 C21 C20 119.8(3) . . ? C21 C22 C23 120.0(3) . . ? C22 C23 C24 119.9(3) . . ? C19 C24 C23 121.1(3) . . ? O8A C1A C19A 109.1(2) . . ? O8A C1A C2A 107.8(2) . . ? C19A C1A C2A 108.4(2) . . ? O8A C1A C6A 100.66(19) . . ? C19A C1A C6A 114.1(2) . . ? C2A C1A C6A 116.3(2) . . ? C3A C2A C1A 114.3(2) . . ? C4A C3A C2A 113.5(3) . . ? O17A C4A C3A 124.2(4) . . ? O17A C4A C5A 121.8(4) . . ? C3A C4A C5A 113.8(3) . . ? O8A C5A C7A 105.7(2) . . ? O8A C5A C4A 107.6(3) . . ? C7A C5A C4A 110.1(3) . . ? C9A C6A C16A 104.9(2) . . ? C9A C6A C7A 110.1(2) . . ? C16A C6A C7A 112.0(3) . . ? C9A C6A C1A 116.4(2) . . ? C16A C6A C1A 112.4(2) . . ? C7A C6A C1A 101.3(2) . . ? C5A C7A C6A 104.2(2) . . ? C5A O8A C1A 104.6(2) . . ? O18A C9A C10A 126.2(3) . . ? O18A C9A C6A 126.1(3) . . ? C10A C9A C6A 107.6(2) . . ? C15A C10A C11A 122.2(3) . . ? C15A C10A C9A 110.0(3) . . ? C11A C10A C9A 127.8(3) . . ? C12A C11A C10A 118.0(4) . . ? C11A C12A C13A 119.8(4) . . ? C14A C13A C12A 122.2(4) . . ? C13A C14A C15A 118.3(4) . . ? C10A C15A C14A 119.4(3) . . ? C10A C15A C16A 112.3(3) . . ? C14A C15A C16A 128.3(3) . . ? C15A C16A C6A 105.1(3) . . ? C20A C19A C24A 118.7(3) . . ? C20A C19A C1A 121.8(2) . . ? C24A C19A C1A 119.5(3) . . ? C19A C20A C21A 120.4(3) . . ? C22A C21A C20A 120.7(3) . . ? C21A C22A C23A 119.9(3) . . ? C22A C23A C24A 119.9(3) . . ? C19A C24A C23A 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.192 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.049 #===END #===END data_8a _database_code_depnum_ccdc_archive 'CCDC 267635' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'oxabridged spirocyclic six-membered-ring system' _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 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 11.322(3) _cell_length_b 9.237(2) _cell_length_c 13.982(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.010(5) _cell_angle_gamma 90.00 _cell_volume 1424.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description CHUNKY _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD AREA DETECTOR' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7232 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.19 _reflns_number_total 3124 _reflns_number_gt 1676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP, PLATON' _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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 3124 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1306 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1879 _refine_ls_wR_factor_gt 0.1558 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O7 O 0.12497(16) 0.00835(16) 0.24539(12) 0.0426(5) Uani 1 d . . . O14 O -0.12097(18) 0.1137(2) 0.28230(14) 0.0591(6) Uani 1 d . . . O2 O 0.17241(18) 0.1023(2) 0.02097(15) 0.0605(6) Uani 1 d . . . C3 C 0.1695(2) 0.1013(3) 0.10662(19) 0.0428(6) Uani 1 d . . . C5 C 0.0038(2) 0.2033(2) 0.17417(17) 0.0400(6) Uani 1 d . . . C8 C -0.1139(2) 0.1638(2) 0.20350(19) 0.0442(7) Uani 1 d . . . C6 C 0.1025(2) 0.2561(3) 0.26124(18) 0.0453(7) Uani 1 d . . . H61 H 0.0703 0.2669 0.3195 0.054 Uiso 1 calc R . . H62 H 0.1355 0.3482 0.2465 0.054 Uiso 1 calc R . . C12A C -0.1709(2) 0.2731(3) 0.05105(18) 0.0442(7) Uani 1 d . . . C4 C 0.0641(2) 0.0584(2) 0.15112(17) 0.0386(6) Uani 1 d . . . H4 H 0.0079 -0.0115 0.1124 0.046 Uiso 1 calc R . . C2 C 0.2710(2) 0.1436(3) 0.1931(2) 0.0467(7) Uani 1 d . . . C13 C -0.0386(2) 0.3013(3) 0.08369(19) 0.0475(7) Uani 1 d . . . H131 H -0.0234 0.4024 0.1010 0.057 Uiso 1 calc R . . H132 H 0.0031 0.2766 0.0324 0.057 Uiso 1 calc R . . C1 C 0.2000(2) 0.1368(2) 0.27585(18) 0.0419(6) Uani 1 d . . . C8A C -0.2143(2) 0.1964(3) 0.12062(19) 0.0450(7) Uani 1 d . . . C9 C -0.3358(3) 0.1626(3) 0.1085(2) 0.0635(9) Uani 1 d . . . H9 H -0.3634 0.1124 0.1569 0.076 Uiso 1 calc R . . C12 C -0.2515(3) 0.3135(3) -0.0354(2) 0.0598(8) Uani 1 d . . . H12 H -0.2244 0.3626 -0.0845 0.072 Uiso 1 calc R . . C10 C -0.4137(3) 0.2042(4) 0.0246(3) 0.0759(10) Uani 1 d . . . H10 H -0.4957 0.1822 0.0149 0.091 Uiso 1 calc R . . C15 C 0.2713(3) 0.1207(3) 0.3787(2) 0.0620(8) Uani 1 d . . . H153 H 0.2170 0.1097 0.4219 0.093 Uiso 1 calc R . . H152 H 0.3206 0.2052 0.3971 0.093 Uiso 1 calc R . . H151 H 0.3224 0.0368 0.3833 0.093 Uiso 1 calc R . . C16 C 0.3683(3) 0.0257(3) 0.2056(2) 0.0678(9) Uani 1 d . . . H162 H 0.3352 -0.0642 0.2220 0.102 Uiso 1 calc R . . H163 H 0.4360 0.0527 0.2573 0.102 Uiso 1 calc R . . H161 H 0.3948 0.0147 0.1454 0.102 Uiso 1 calc R . . C17 C 0.3257(3) 0.2907(3) 0.1777(3) 0.0701(9) Uani 1 d . . . H173 H 0.3695 0.2831 0.1266 0.105 Uiso 1 calc R . . H172 H 0.3800 0.3207 0.2375 0.105 Uiso 1 calc R . . H171 H 0.2620 0.3608 0.1593 0.105 Uiso 1 calc R . . C11 C -0.3719(3) 0.2791(4) -0.0465(2) 0.0757(10) Uani 1 d . . . H11 H -0.4267 0.3071 -0.1036 0.091 Uiso 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 O7 0.0541(11) 0.0295(8) 0.0430(11) 0.0009(7) 0.0084(8) -0.0013(8) O14 0.0752(14) 0.0546(12) 0.0559(13) 0.0163(10) 0.0321(10) 0.0088(10) O2 0.0707(14) 0.0678(13) 0.0477(12) -0.0055(10) 0.0233(10) -0.0001(11) C3 0.0518(16) 0.0336(13) 0.0447(17) -0.0033(11) 0.0143(13) 0.0050(12) C5 0.0491(16) 0.0320(12) 0.0418(15) 0.0002(10) 0.0164(12) 0.0025(11) C8 0.0600(18) 0.0312(12) 0.0462(17) 0.0017(11) 0.0224(14) 0.0061(12) C6 0.0567(17) 0.0339(13) 0.0467(16) -0.0072(11) 0.0145(13) 0.0000(12) C12A 0.0572(17) 0.0345(13) 0.0431(16) -0.0003(11) 0.0161(13) 0.0102(12) C4 0.0467(15) 0.0311(12) 0.0370(15) -0.0037(10) 0.0073(12) -0.0022(11) C2 0.0450(16) 0.0404(14) 0.0571(18) -0.0040(12) 0.0165(13) -0.0031(12) C13 0.0597(18) 0.0374(14) 0.0498(17) 0.0078(11) 0.0215(13) 0.0043(13) C1 0.0457(15) 0.0318(13) 0.0462(16) -0.0053(11) 0.0062(12) -0.0043(11) C8A 0.0501(17) 0.0400(14) 0.0480(17) -0.0010(12) 0.0176(13) 0.0076(12) C9 0.055(2) 0.069(2) 0.071(2) 0.0018(16) 0.0212(17) 0.0036(15) C12 0.074(2) 0.0585(18) 0.0483(19) 0.0024(13) 0.0153(16) 0.0155(16) C10 0.0495(19) 0.099(3) 0.077(3) -0.004(2) 0.0082(18) 0.0028(18) C15 0.068(2) 0.0597(18) 0.0525(19) -0.0019(14) 0.0020(15) -0.0019(16) C16 0.0505(18) 0.070(2) 0.083(2) -0.0095(17) 0.0141(16) 0.0084(15) C17 0.073(2) 0.0566(19) 0.085(2) -0.0051(16) 0.0271(18) -0.0221(16) C11 0.070(2) 0.091(3) 0.059(2) -0.0046(18) -0.0012(18) 0.021(2) _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 O7 C4 1.420(3) . ? O7 C1 1.466(3) . ? O14 C8 1.214(3) . ? O2 C3 1.205(3) . ? C3 C4 1.517(4) . ? C3 C2 1.520(4) . ? C5 C8 1.525(4) . ? C5 C6 1.534(3) . ? C5 C13 1.542(3) . ? C5 C4 1.568(3) . ? C8 C8A 1.460(4) . ? C6 C1 1.541(4) . ? C12A C8A 1.380(3) . ? C12A C12 1.391(4) . ? C12A C13 1.488(4) . ? C2 C17 1.528(4) . ? C2 C16 1.531(4) . ? C2 C1 1.552(4) . ? C1 C15 1.489(4) . ? C8A C9 1.384(4) . ? C9 C10 1.355(4) . ? C12 C11 1.374(5) . ? C10 C11 1.380(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 C4 O7 C1 97.72(16) . . ? O2 C3 C4 127.5(2) . . ? O2 C3 C2 127.1(2) . . ? C4 C3 C2 105.4(2) . . ? C8 C5 C6 112.8(2) . . ? C8 C5 C13 103.4(2) . . ? C6 C5 C13 120.1(2) . . ? C8 C5 C4 107.35(18) . . ? C6 C5 C4 99.30(19) . . ? C13 C5 C4 113.70(19) . . ? O14 C8 C8A 126.9(2) . . ? O14 C8 C5 125.1(2) . . ? C8A C8 C5 108.0(2) . . ? C5 C6 C1 104.49(19) . . ? C8A C12A C12 118.8(3) . . ? C8A C12A C13 111.6(2) . . ? C12 C12A C13 129.6(2) . . ? O7 C4 C3 101.72(19) . . ? O7 C4 C5 103.29(17) . . ? C3 C4 C5 106.29(18) . . ? C3 C2 C17 112.0(2) . . ? C3 C2 C16 107.7(2) . . ? C17 C2 C16 110.2(2) . . ? C3 C2 C1 99.0(2) . . ? C17 C2 C1 115.8(2) . . ? C16 C2 C1 111.5(2) . . ? C12A C13 C5 104.8(2) . . ? O7 C1 C15 110.6(2) . . ? O7 C1 C6 100.88(19) . . ? C15 C1 C6 114.6(2) . . ? O7 C1 C2 100.36(17) . . ? C15 C1 C2 117.7(2) . . ? C6 C1 C2 110.4(2) . . ? C12A C8A C9 122.1(3) . . ? C12A C8A C8 109.2(2) . . ? C9 C8A C8 128.7(3) . . ? C10 C9 C8A 118.5(3) . . ? C11 C12 C12A 118.4(3) . . ? C9 C10 C11 120.3(3) . . ? C12 C11 C10 121.8(3) . . ? _diffrn_measured_fraction_theta_max 0.840 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.840 _refine_diff_density_max 0.309 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.071