# 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_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Klussmann, Martin' _publ_contact_author_email klusi@mpi-muelheim.mpg.de _publ_section_title ; Lewis-Acid Catalysed One Pot Synthesis of Substituted Xanthenes ; _publ_author_name M.Klussmann # Attachment '7060final.cif' data_7060sadabs _database_code_depnum_ccdc_archive 'CCDC 797428' #TrackingRef '7060final.cif' _audit_creation_date 2010-08-12 _audit_block_code BSR-BC-106-01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Title ; _chemical_melting_point 100 _chemical_compound_source diethylether,pentane _chemical_formula_moiety 'C18 H14 O' _chemical_formula_sum 'C18 H14 O' _chemical_formula_weight 246.29 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 ? _symmetry_space_group_name_H-M 'p 21/c' _symmetry_space_group_name_Hall '-p 2ybc' _symmetry_Int_Tables_number 14 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 4.7615(5) _cell_length_b 11.9406(12) _cell_length_c 21.373(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.296(2) _cell_angle_gamma 90.00 _cell_volume 1213.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 9977 _cell_measurement_theta_min 2.5601 _cell_measurement_theta_max 35.2873 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 2.00 0.0100 0.00 -1.00 -2.00 0.0100 1.00 -1.00 0.00 0.0400 -1.00 1.00 0.00 0.0600 -1.00 -2.00 1.00 0.0400 1.00 2.00 -1.00 0.0200 0.00 -2.00 1.00 0.0400 0.00 2.00 -1.00 0.0200 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method ? _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.99418 _exptl_absorpt_correction_T_max 0.99853 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'Incoatec Helios mirrors' _diffrn_measurement_device_type 'Bruker-AXS Kappa Mach3 APEX-II' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 66.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 69156 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 35.47 _reflns_number_total 5495 _reflns_number_gt 4430 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.7386 and 1.0000 (SADABS). Highest peak 0.63 at 0.0624 0.1806 0.0208 [ 0.69 A from C16 ] Deepest hole -0.22 at 0.0796 0.3123 0.4707 [ 0.69 A from C16 ] ; _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^)+(0.0741P)^2^+0.2634P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5495 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 1.65465(16) 0.18478(7) 0.63717(4) 0.01800(14) Uani 1 1 d . . . H1B H 1.6028 0.1138 0.6541 0.027 Uiso 1 1 calc R . . H1C H 1.6681 0.2396 0.6701 0.027 Uiso 1 1 calc R . . H1A H 1.8332 0.1780 0.6188 0.027 Uiso 1 1 calc R . . C2 C 1.43498(15) 0.22071(6) 0.58780(3) 0.01424(13) Uani 1 1 d . . . C3 C 1.35966(15) 0.15130(6) 0.53712(3) 0.01412(13) Uani 1 1 d . . . H3 H 1.4480 0.0822 0.5343 0.017 Uiso 1 1 calc R . . C4 C 1.15676(14) 0.18155(6) 0.49039(3) 0.01225(12) Uani 1 1 d . . . C5 C 1.08767(15) 0.10622(6) 0.43529(3) 0.01331(12) Uani 1 1 d . . . H5B H 1.0330 0.0332 0.4503 0.016 Uiso 1 1 calc R . . H5A H 1.2542 0.0965 0.4118 0.016 Uiso 1 1 calc R . . C6 C 0.85389(14) 0.15262(6) 0.39264(3) 0.01247(12) Uani 1 1 d . . . C7 C 0.75395(15) 0.09092(6) 0.33921(3) 0.01497(13) Uani 1 1 d . . . H7 H 0.8319 0.0211 0.3317 0.018 Uiso 1 1 calc R . . C8 C 0.54587(16) 0.13116(6) 0.29828(3) 0.01620(13) Uani 1 1 d . . . H8 H 0.4859 0.0891 0.2634 0.019 Uiso 1 1 calc R . . C9 C 0.42149(15) 0.23729(6) 0.30912(3) 0.01371(12) Uani 1 1 d . . . C10 C 0.20323(16) 0.28174(7) 0.26855(3) 0.01633(13) Uani 1 1 d . . . H10 H 0.1394 0.2412 0.2334 0.020 Uiso 1 1 calc R . . C11 C 0.08490(16) 0.38365(7) 0.28042(4) 0.01747(14) Uani 1 1 d . . . H11 H -0.0586 0.4116 0.2535 0.021 Uiso 1 1 calc R . . C12 C 0.18049(16) 0.44627(6) 0.33351(4) 0.01723(14) Uani 1 1 d . . . H12 H 0.1007 0.5157 0.3411 0.021 Uiso 1 1 calc R . . C13 C 0.39077(16) 0.40548(6) 0.37418(3) 0.01507(13) Uani 1 1 d . . . H13 H 0.4508 0.4469 0.4093 0.018 Uiso 1 1 calc R . . C14 C 0.51595(14) 0.30031(6) 0.36262(3) 0.01243(12) Uani 1 1 d . . . C15 C 0.73560(14) 0.25531(6) 0.40331(3) 0.01201(12) Uani 1 1 d . . . C16 C 1.02505(14) 0.28505(6) 0.49560(3) 0.01244(12) Uani 1 1 d . . . C17 C 1.09746(16) 0.35708(6) 0.54512(3) 0.01514(13) Uani 1 1 d . . . H17 H 1.0103 0.4265 0.5477 0.018 Uiso 1 1 calc R . . C18 C 1.30083(16) 0.32459(6) 0.59075(3) 0.01557(13) Uani 1 1 d . . . H18 H 1.3486 0.3728 0.6238 0.019 Uiso 1 1 calc R . . O1 O 0.81832(11) 0.32318(4) 0.45290(2) 0.01414(11) 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 C1 0.0144(3) 0.0231(3) 0.0159(3) 0.0009(2) -0.0046(2) -0.0010(2) C2 0.0113(3) 0.0179(3) 0.0132(3) 0.0006(2) -0.0018(2) -0.0019(2) C3 0.0120(3) 0.0162(3) 0.0139(3) -0.0003(2) -0.0018(2) 0.0003(2) C4 0.0113(3) 0.0135(3) 0.0118(3) -0.0004(2) -0.0009(2) -0.0009(2) C5 0.0137(3) 0.0138(3) 0.0121(3) -0.0010(2) -0.0014(2) 0.0003(2) C6 0.0116(3) 0.0142(3) 0.0115(3) -0.0007(2) -0.0006(2) -0.0011(2) C7 0.0148(3) 0.0161(3) 0.0138(3) -0.0031(2) -0.0009(2) -0.0002(2) C8 0.0159(3) 0.0191(3) 0.0132(3) -0.0030(2) -0.0018(2) -0.0011(2) C9 0.0121(3) 0.0174(3) 0.0115(3) 0.0002(2) -0.0009(2) -0.0020(2) C10 0.0143(3) 0.0217(3) 0.0126(3) 0.0010(2) -0.0027(2) -0.0019(2) C11 0.0142(3) 0.0230(3) 0.0148(3) 0.0036(2) -0.0024(2) -0.0001(2) C12 0.0162(3) 0.0181(3) 0.0171(3) 0.0027(2) -0.0017(2) 0.0016(2) C13 0.0150(3) 0.0156(3) 0.0144(3) 0.0007(2) -0.0013(2) 0.0000(2) C14 0.0109(3) 0.0149(3) 0.0113(3) 0.0007(2) -0.0008(2) -0.0012(2) C15 0.0120(3) 0.0135(3) 0.0103(3) -0.0004(2) -0.0009(2) -0.0018(2) C16 0.0121(3) 0.0137(3) 0.0113(3) 0.0001(2) -0.0018(2) -0.0007(2) C17 0.0176(3) 0.0137(3) 0.0137(3) -0.0016(2) -0.0025(2) -0.0005(2) C18 0.0160(3) 0.0167(3) 0.0135(3) -0.0013(2) -0.0034(2) -0.0024(2) O1 0.0159(2) 0.0137(2) 0.0122(2) -0.00205(16) -0.00467(18) 0.00123(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5047(10) . y C1 H1B 0.9600 . n C1 H1C 0.9600 . n C1 H1A 0.9600 . n C2 C3 1.3944(10) . y C2 C18 1.3983(11) . y C3 C4 1.3965(9) . y C3 H3 0.9300 . n C4 C16 1.3932(10) . y C4 C5 1.5031(10) . y C5 C6 1.5035(10) . y C5 H5B 0.9700 . n C5 H5A 0.9700 . n C6 C15 1.3738(10) . y C6 C7 1.4179(10) . y C7 C8 1.3704(10) . y C7 H7 0.9300 . n C8 C9 1.4235(11) . y C8 H8 0.9300 . n C9 C10 1.4177(10) . y C9 C14 1.4202(10) . y C10 C11 1.3707(11) . y C10 H10 0.9300 . n C11 C12 1.4123(11) . y C11 H11 0.9300 . n C12 C13 1.3767(10) . y C12 H12 0.9300 . n C13 C14 1.4178(10) . y C13 H13 0.9300 . n C14 C15 1.4262(9) . y C15 O1 1.3739(8) . y C16 O1 1.3804(8) . y C16 C17 1.3919(10) . y C17 C18 1.3894(10) . y C17 H17 0.9300 . n C18 H18 0.9300 . n loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1B 109.5 . . n C2 C1 H1C 109.5 . . n H1B C1 H1C 109.5 . . n C2 C1 H1A 109.5 . . n H1B C1 H1A 109.5 . . n H1C C1 H1A 109.5 . . n C3 C2 C18 117.67(6) . . y C3 C2 C1 120.84(7) . . y C18 C2 C1 121.49(6) . . y C2 C3 C4 122.57(7) . . y C2 C3 H3 118.7 . . n C4 C3 H3 118.7 . . n C16 C4 C3 117.93(6) . . y C16 C4 C5 120.94(6) . . y C3 C4 C5 121.11(6) . . y C4 C5 C6 112.06(6) . . y C4 C5 H5B 109.2 . . n C6 C5 H5B 109.2 . . n C4 C5 H5A 109.2 . . n C6 C5 H5A 109.2 . . n H5B C5 H5A 107.9 . . n C15 C6 C7 118.40(6) . . y C15 C6 C5 121.64(6) . . y C7 C6 C5 119.96(6) . . y C8 C7 C6 121.92(7) . . y C8 C7 H7 119.0 . . n C6 C7 H7 119.0 . . n C7 C8 C9 120.03(6) . . y C7 C8 H8 120.0 . . n C9 C8 H8 120.0 . . n C10 C9 C14 118.76(7) . . y C10 C9 C8 122.07(6) . . y C14 C9 C8 119.17(6) . . y C11 C10 C9 120.92(7) . . y C11 C10 H10 119.5 . . n C9 C10 H10 119.5 . . n C10 C11 C12 120.11(7) . . y C10 C11 H11 119.9 . . n C12 C11 H11 119.9 . . n C13 C12 C11 120.61(7) . . y C13 C12 H12 119.7 . . n C11 C12 H12 119.7 . . n C12 C13 C14 120.07(7) . . y C12 C13 H13 120.0 . . n C14 C13 H13 120.0 . . n C13 C14 C9 119.52(6) . . y C13 C14 C15 121.90(6) . . y C9 C14 C15 118.58(6) . . y O1 C15 C6 123.53(6) . . y O1 C15 C14 114.57(6) . . y C6 C15 C14 121.89(6) . . y O1 C16 C17 115.78(6) . . y O1 C16 C4 123.16(6) . . y C17 C16 C4 121.06(6) . . y C18 C17 C16 119.56(7) . . y C18 C17 H17 120.2 . . n C16 C17 H17 120.2 . . n C17 C18 C2 121.19(6) . . y C17 C18 H18 119.4 . . n C2 C18 H18 119.4 . . n C15 O1 C16 118.51(5) . . y _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 35.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.627 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.065 _chemical_absolute_configuration rmad _chemical_name_common Title # Attachment '7104final.cif' data_7104SADABS _database_code_depnum_ccdc_archive 'CCDC 797429' #TrackingRef '7104final.cif' _audit_creation_date 2010-09-13 _audit_block_code BSR-BC-126-01 _audit_creation_method SHELXL-97 _chemical_absolute_configuration ? _chemical_compound_source 'Et2O, pentane' _chemical_formula_moiety 'C16 H16 O2' _chemical_formula_sum 'C16 H16 O2' _chemical_formula_weight 240.29 _chemical_melting_point ? _chemical_name_common Title _chemical_name_systematic ; Title ; 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 _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0500 0.00 0.00 -1.00 0.0300 -1.00 0.00 0.00 0.1700 1.00 0.00 0.00 0.1800 0.00 -4.00 1.00 0.0600 0.00 1.00 0.00 0.0400 1.00 -3.00 0.00 0.1000 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_angle_alpha 99.79(2) _cell_angle_beta 110.27(2) _cell_angle_gamma 98.47(3) _cell_formula_units_Z 2 _cell_length_a 7.3745(19) _cell_length_b 8.763(3) _cell_length_c 10.395(2) _cell_measurement_reflns_used 12671 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.9961 _cell_measurement_theta_min 2.8224 _cell_volume 605.3(3) _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.99359 _exptl_absorpt_correction_T_min 0.98013 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_F_000 256 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description prism _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 11977 _diffrn_reflns_theta_full 34.06 _diffrn_reflns_theta_max 34.06 _diffrn_reflns_theta_min 2.83 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3839 _reflns_number_total 4896 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.557 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.055 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0456 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 166 _refine_ls_number_reflns 4896 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1220 _refine_ls_wR_factor_ref 0.1339 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.1150P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _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. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.7973 and 1.0000 (SADABS). Highest peak ? Deepest hole ? ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.74981(11) 0.22110(7) 0.59864(6) 0.01786(14) Uani 1 1 d . . . O2 O 0.81735(10) 0.83486(7) 0.87933(7) 0.01916(14) Uani 1 1 d . . . C1 C 0.73951(12) 0.18146(10) 0.46116(8) 0.01414(15) Uani 1 1 d . . . C2 C 0.74027(13) 0.02305(10) 0.41310(9) 0.01631(16) Uani 1 1 d . . . H2 H 0.7499 -0.0458 0.4729 0.020 Uiso 1 1 calc R . . C3 C 0.72657(13) -0.03186(10) 0.27544(9) 0.01545(15) Uani 1 1 d . . . C4 C 0.71019(13) 0.07476(10) 0.18802(8) 0.01537(15) Uani 1 1 d . . . H4 H 0.6982 0.0387 0.0953 0.018 Uiso 1 1 calc R . . C5 C 0.71145(12) 0.23390(10) 0.23636(8) 0.01402(15) Uani 1 1 d . . . C6 C 0.72826(12) 0.29070(9) 0.37626(8) 0.01273(14) Uani 1 1 d . . . C7 C 0.73530(12) 0.46301(9) 0.43274(8) 0.01341(15) Uani 1 1 d . . . H7B H 0.8452 0.5293 0.4231 0.016 Uiso 1 1 calc R . . H7A H 0.6140 0.4897 0.3768 0.016 Uiso 1 1 calc R . . C8 C 0.75927(12) 0.49830(9) 0.58580(8) 0.01263(14) Uani 1 1 d . . . C9 C 0.77678(12) 0.65393(10) 0.65826(8) 0.01392(15) Uani 1 1 d . . . H9 H 0.7750 0.7357 0.6116 0.017 Uiso 1 1 calc R . . C10 C 0.79689(12) 0.68746(10) 0.79948(8) 0.01444(15) Uani 1 1 d . . . C11 C 0.79886(13) 0.56376(10) 0.86972(8) 0.01570(15) Uani 1 1 d . . . H11 H 0.8112 0.5850 0.9635 0.019 Uiso 1 1 calc R . . C12 C 0.78243(13) 0.41035(10) 0.79934(8) 0.01533(15) Uani 1 1 d . . . H12 H 0.7844 0.3286 0.8459 0.018 Uiso 1 1 calc R . . C13 C 0.76289(12) 0.37818(9) 0.65811(8) 0.01358(14) Uani 1 1 d . . . C14 C 0.73303(15) -0.20214(11) 0.22357(10) 0.02034(18) Uani 1 1 d . . . H14C H 0.8574 -0.2218 0.2797 0.031 Uiso 1 1 calc R . . H14B H 0.7192 -0.2204 0.1266 0.031 Uiso 1 1 calc R . . H14A H 0.6265 -0.2723 0.2315 0.031 Uiso 1 1 calc R . . C15 C 0.69769(14) 0.34599(11) 0.14020(9) 0.01767(16) Uani 1 1 d . . . H15C H 0.8167 0.4281 0.1781 0.027 Uiso 1 1 calc R . . H15A H 0.5858 0.3927 0.1329 0.027 Uiso 1 1 calc R . . H15B H 0.6818 0.2886 0.0483 0.027 Uiso 1 1 calc R . . C16 C 0.80078(14) 0.96268(10) 0.80984(9) 0.01826(17) Uani 1 1 d . . . H16C H 0.8204 1.0596 0.8770 0.027 Uiso 1 1 calc R . . H16A H 0.6713 0.9408 0.7365 0.027 Uiso 1 1 calc R . . H16B H 0.8995 0.9734 0.7694 0.027 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 0.0295(4) 0.0146(3) 0.0124(3) 0.0042(2) 0.0100(2) 0.0072(2) O2 0.0279(4) 0.0151(3) 0.0132(3) 0.0015(2) 0.0067(2) 0.0059(2) C1 0.0154(4) 0.0162(3) 0.0112(3) 0.0030(3) 0.0053(3) 0.0042(3) C2 0.0191(4) 0.0153(3) 0.0151(3) 0.0039(3) 0.0066(3) 0.0051(3) C3 0.0142(4) 0.0157(3) 0.0154(3) 0.0010(3) 0.0053(3) 0.0039(3) C4 0.0148(4) 0.0184(4) 0.0127(3) 0.0017(3) 0.0057(3) 0.0042(3) C5 0.0126(3) 0.0180(3) 0.0117(3) 0.0036(3) 0.0047(3) 0.0037(3) C6 0.0121(3) 0.0149(3) 0.0116(3) 0.0036(3) 0.0047(3) 0.0034(3) C7 0.0150(4) 0.0153(3) 0.0106(3) 0.0041(2) 0.0051(3) 0.0040(3) C8 0.0122(3) 0.0145(3) 0.0111(3) 0.0029(2) 0.0045(3) 0.0030(3) C9 0.0146(4) 0.0149(3) 0.0125(3) 0.0039(3) 0.0049(3) 0.0037(3) C10 0.0142(4) 0.0150(3) 0.0129(3) 0.0017(3) 0.0043(3) 0.0035(3) C11 0.0182(4) 0.0183(3) 0.0113(3) 0.0037(3) 0.0059(3) 0.0053(3) C12 0.0184(4) 0.0172(3) 0.0126(3) 0.0055(3) 0.0070(3) 0.0056(3) C13 0.0155(4) 0.0140(3) 0.0119(3) 0.0029(2) 0.0057(3) 0.0042(3) C14 0.0232(4) 0.0169(4) 0.0199(4) 0.0008(3) 0.0081(3) 0.0056(3) C15 0.0204(4) 0.0218(4) 0.0130(3) 0.0055(3) 0.0080(3) 0.0058(3) C16 0.0208(4) 0.0154(3) 0.0181(4) 0.0034(3) 0.0067(3) 0.0050(3) _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 1.3846(10) . ? O1 C13 1.3843(11) . ? O2 C10 1.3679(11) . ? O2 C16 1.4302(12) . ? C1 C2 1.3946(12) . ? C1 C6 1.4007(12) . ? C2 H2 0.9300 . ? C2 C3 1.3932(12) . ? C3 C4 1.3997(12) . ? C3 C14 1.5115(13) . ? C4 H4 0.9300 . ? C4 C5 1.3971(12) . ? C5 C6 1.4102(11) . ? C5 C15 1.5057(12) . ? C6 C7 1.5106(12) . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C7 C8 1.5100(11) . ? C8 C9 1.4054(12) . ? C8 C13 1.3918(12) . ? C9 H9 0.9300 . ? C9 C10 1.3974(11) . ? C10 C11 1.4054(12) . ? C11 H11 0.9300 . ? C11 C12 1.3832(12) . ? C12 H12 0.9300 . ? C12 C13 1.3987(11) . ? C14 H14C 0.9600 . ? C14 H14B 0.9600 . ? C14 H14A 0.9600 . ? C15 H15C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C16 H16C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? 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 C2 114.58(7) . . ? O1 C1 C6 123.05(7) . . ? O1 C13 C8 123.68(7) . . ? O1 C13 C12 115.16(7) . . ? O2 C10 C9 125.22(8) . . ? O2 C10 C11 115.26(7) . . ? O2 C16 H16C 109.5 . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? C1 C2 H2 120.0 . . ? C1 C6 C5 117.46(8) . . ? C1 C6 C7 121.26(7) . . ? C2 C1 C6 122.37(8) . . ? C2 C3 C4 118.47(8) . . ? C2 C3 C14 120.33(8) . . ? C3 C2 C1 119.90(8) . . ? C3 C2 H2 120.0 . . ? C3 C4 H4 119.1 . . ? C3 C14 H14C 109.5 . . ? C3 C14 H14B 109.5 . . ? C3 C14 H14A 109.5 . . ? C4 C3 C14 121.19(8) . . ? C4 C5 C6 120.03(8) . . ? C4 C5 C15 120.26(7) . . ? C5 C4 C3 121.73(8) . . ? C5 C4 H4 119.1 . . ? C5 C6 C7 121.28(7) . . ? C5 C15 H15C 109.5 . . ? C5 C15 H15A 109.5 . . ? C5 C15 H15B 109.5 . . ? C6 C5 C15 119.70(8) . . ? C6 C7 H7B 109.1 . . ? C6 C7 H7A 109.1 . . ? H7B C7 H7A 107.9 . . ? C8 C7 C6 112.28(7) . . ? C8 C7 H7B 109.1 . . ? C8 C7 H7A 109.1 . . ? C8 C9 H9 119.6 . . ? C8 C13 C12 121.17(8) . . ? C9 C8 C7 120.46(7) . . ? C9 C10 C11 119.52(8) . . ? C10 O2 C16 117.41(7) . . ? C10 C9 C8 120.88(7) . . ? C10 C9 H9 119.6 . . ? C10 C11 H11 120.0 . . ? C11 C12 H12 120.0 . . ? C11 C12 C13 120.03(8) . . ? C12 C11 C10 119.97(8) . . ? C12 C11 H11 120.0 . . ? C13 O1 C1 118.47(7) . . ? C13 C8 C7 121.11(7) . . ? C13 C8 C9 118.43(7) . . ? C13 C12 H12 120.0 . . ? H14C C14 H14B 109.5 . . ? H14C C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? H15C C15 H15A 109.5 . . ? H15C C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? H16C C16 H16A 109.5 . . ? H16C C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? 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 178.75(7) . . . . ? O1 C1 C6 C5 -177.83(7) . . . . ? O1 C1 C6 C7 2.58(13) . . . . ? O2 C10 C11 C12 -178.96(8) . . . . ? C1 O1 C13 C8 2.36(12) . . . . ? C1 O1 C13 C12 -177.03(7) . . . . ? C1 C2 C3 C4 -0.66(13) . . . . ? C1 C2 C3 C14 178.28(8) . . . . ? C1 C6 C7 C8 1.17(11) . . . . ? C2 C1 C6 C5 1.87(13) . . . . ? C2 C1 C6 C7 -177.72(8) . . . . ? C2 C3 C4 C5 1.34(13) . . . . ? C3 C4 C5 C6 -0.41(13) . . . . ? C3 C4 C5 C15 178.76(8) . . . . ? C4 C5 C6 C1 -1.17(12) . . . . ? C4 C5 C6 C7 178.42(7) . . . . ? C5 C6 C7 C8 -178.40(7) . . . . ? C6 C1 C2 C3 -0.97(14) . . . . ? C6 C7 C8 C9 177.44(7) . . . . ? C6 C7 C8 C13 -3.11(11) . . . . ? C7 C8 C9 C10 179.31(7) . . . . ? C7 C8 C13 O1 1.51(13) . . . . ? C7 C8 C13 C12 -179.14(7) . . . . ? C8 C9 C10 O2 179.13(8) . . . . ? C8 C9 C10 C11 -0.24(13) . . . . ? C9 C8 C13 O1 -179.03(7) . . . . ? C9 C8 C13 C12 0.32(13) . . . . ? C9 C10 C11 C12 0.47(13) . . . . ? C10 C11 C12 C13 -0.31(13) . . . . ? C11 C12 C13 O1 179.31(7) . . . . ? C11 C12 C13 C8 -0.09(13) . . . . ? C13 O1 C1 C2 175.85(7) . . . . ? C13 O1 C1 C6 -4.43(12) . . . . ? C13 C8 C9 C10 -0.15(12) . . . . ? C14 C3 C4 C5 -177.59(8) . . . . ? C15 C5 C6 C1 179.66(7) . . . . ? C15 C5 C6 C7 -0.75(12) . . . . ? C16 O2 C10 C9 5.37(13) . . . . ? C16 O2 C10 C11 -175.24(7) . . . . ?