Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Organic & Biomolecular Chemistry' _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Paul Clarke' _publ_contact_author_address ; School of Chemistry University of Nottingham Nottingham NG7 2RD UNITED KINGDOM ; _publ_contact_author_email PAUL.CLARKE@NOTTINGHAM.AC.UK _publ_section_title ; Teaching an Old Dog New Tricks: Revisiting the Maitland-Japp Reaction. The One Pot, Multi-Component Construction of Highly Substituted Tetrahydropyran-4-ones. ; loop_ _publ_author_name 'Paul A. Clarke' 'William H. C. Martin' 'Jason M. Hargreaves' 'Claire Wilson' 'Alexander J. Blake' data_5b _database_code_depnum_ccdc_archive 'CCDC 250776' # DIPHPY #3377 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 O4' _chemical_formula_sum 'C19 H18 O4' _chemical_formula_weight 310.33 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 13.0132(10) _cell_length_b 8.6004(7) _cell_length_c 14.1620(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.558(2) _cell_angle_gamma 90.00 _cell_volume 1584.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3436 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.75 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8847 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.037 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 28.81 _reflns_number_total 3656 _reflns_number_gt 2746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _refine_special_details ; ? ; _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^)+(0.054P)^2^+0.042P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3656 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.105 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.88132(6) 0.01580(9) 0.74668(5) 0.0259(2) Uani 1 1 d . . . C2 C 0.97794(9) 0.01206(13) 0.79696(8) 0.0249(3) Uani 1 1 d . . . H2A H 0.9853 -0.0908 0.8294 0.030 Uiso 1 1 calc R . . C3 C 0.98179(9) 0.14105(14) 0.87200(8) 0.0278(3) Uani 1 1 d . . . H3A H 1.0457 0.1305 0.9109 0.033 Uiso 1 1 calc R . . H3B H 0.9832 0.2436 0.8403 0.033 Uiso 1 1 calc R . . C4 C 0.89110(9) 0.13361(13) 0.93458(8) 0.0270(3) Uani 1 1 d . . . O4 O 0.89674(7) 0.15137(11) 1.01950(6) 0.0369(2) Uani 1 1 d . . . C5 C 0.78875(9) 0.10533(14) 0.88281(8) 0.0268(3) Uani 1 1 d . . . H5A H 0.7700 0.2043 0.8496 0.032 Uiso 1 1 calc R . . C6 C 0.79813(9) -0.02154(13) 0.80560(8) 0.0243(3) Uani 1 1 d . . . H6A H 0.8112 -0.1246 0.8363 0.029 Uiso 1 1 calc R . . C51 C 0.70388(9) 0.07113(15) 0.95001(9) 0.0316(3) Uani 1 1 d . . . O51 O 0.63221(7) 0.15520(12) 0.96381(7) 0.0488(3) Uani 1 1 d . . . O52 O 0.71779(7) -0.06703(11) 0.99113(6) 0.0374(2) Uani 1 1 d . . . C52 C 0.63897(11) -0.1159(2) 1.05502(10) 0.0523(4) Uani 1 1 d . . . H52A H 0.6569 -0.2180 1.0814 0.078 Uiso 1 1 calc R . . H52B H 0.5728 -0.1227 1.0205 0.078 Uiso 1 1 calc R . . H52C H 0.6339 -0.0400 1.1063 0.078 Uiso 1 1 calc R . . C1P C 1.06302(9) 0.02871(13) 0.72737(8) 0.0247(3) Uani 1 1 d . . . C2P C 1.16341(10) -0.00391(14) 0.75719(9) 0.0304(3) Uani 1 1 d . . . H2PA H 1.1774 -0.0342 0.8208 0.036 Uiso 1 1 calc R . . C3P C 1.24297(10) 0.00753(15) 0.69469(9) 0.0336(3) Uani 1 1 d . . . H3PA H 1.3115 -0.0136 0.7158 0.040 Uiso 1 1 calc R . . C4P C 1.22336(10) 0.04957(14) 0.60160(9) 0.0333(3) Uani 1 1 d . . . H4PA H 1.2780 0.0554 0.5586 0.040 Uiso 1 1 calc R . . C5P C 1.12371(10) 0.08309(15) 0.57160(9) 0.0323(3) Uani 1 1 d . . . H5PA H 1.1100 0.1125 0.5078 0.039 Uiso 1 1 calc R . . C6P C 1.04375(9) 0.07388(14) 0.63424(8) 0.0288(3) Uani 1 1 d . . . H6PA H 0.9757 0.0985 0.6135 0.035 Uiso 1 1 calc R . . C7P C 0.70072(9) -0.03014(13) 0.74567(8) 0.0251(3) Uani 1 1 d . . . C8P C 0.62269(9) -0.13216(14) 0.76984(8) 0.0291(3) Uani 1 1 d . . . H8PA H 0.6321 -0.1989 0.8228 0.035 Uiso 1 1 calc R . . C9P C 0.53152(9) -0.13719(16) 0.71734(9) 0.0333(3) Uani 1 1 d . . . H9PA H 0.4788 -0.2073 0.7344 0.040 Uiso 1 1 calc R . . C10P C 0.51699(9) -0.04042(16) 0.64011(9) 0.0339(3) Uani 1 1 d . . . H10A H 0.4546 -0.0447 0.6037 0.041 Uiso 1 1 calc R . . C11P C 0.59374(10) 0.06267(15) 0.61611(9) 0.0334(3) Uani 1 1 d . . . H11A H 0.5835 0.1302 0.5636 0.040 Uiso 1 1 calc R . . C12P C 0.68529(9) 0.06787(14) 0.66818(8) 0.0297(3) Uani 1 1 d . . . H12A H 0.7377 0.1385 0.6510 0.036 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 0.0236(4) 0.0324(5) 0.0215(4) -0.0001(3) -0.0029(3) -0.0016(3) C2 0.0267(6) 0.0239(6) 0.0237(6) 0.0014(4) -0.0060(5) -0.0006(5) C3 0.0318(6) 0.0245(6) 0.0267(6) -0.0002(5) -0.0059(5) -0.0034(5) C4 0.0372(7) 0.0188(6) 0.0249(6) -0.0004(4) -0.0041(5) 0.0003(5) O4 0.0451(5) 0.0415(6) 0.0237(5) -0.0032(4) -0.0051(4) -0.0037(4) C5 0.0326(6) 0.0243(6) 0.0234(6) -0.0003(4) -0.0019(5) 0.0032(5) C6 0.0275(6) 0.0240(6) 0.0215(6) 0.0009(4) -0.0009(5) 0.0004(5) C51 0.0331(7) 0.0358(7) 0.0257(6) -0.0071(5) -0.0028(5) 0.0013(6) O51 0.0418(6) 0.0524(7) 0.0526(6) -0.0097(5) 0.0090(5) 0.0116(5) O52 0.0388(5) 0.0428(6) 0.0309(5) 0.0061(4) 0.0047(4) -0.0022(4) C52 0.0489(9) 0.0707(11) 0.0379(8) 0.0065(7) 0.0107(7) -0.0160(8) C1P 0.0272(6) 0.0197(5) 0.0269(6) -0.0022(4) -0.0031(5) -0.0023(4) C2P 0.0315(7) 0.0318(7) 0.0276(6) 0.0006(5) -0.0037(5) 0.0010(5) C3P 0.0275(7) 0.0369(7) 0.0361(7) -0.0023(5) -0.0028(5) 0.0020(5) C4P 0.0355(7) 0.0317(7) 0.0328(7) -0.0024(5) 0.0057(6) -0.0026(5) C5P 0.0409(7) 0.0295(7) 0.0262(6) 0.0018(5) -0.0016(5) -0.0025(5) C6P 0.0306(6) 0.0259(6) 0.0294(6) 0.0003(5) -0.0055(5) -0.0010(5) C7P 0.0264(6) 0.0273(6) 0.0217(6) -0.0034(4) -0.0007(5) 0.0030(5) C8P 0.0291(6) 0.0324(7) 0.0257(6) 0.0015(5) 0.0008(5) 0.0010(5) C9P 0.0258(6) 0.0420(8) 0.0323(7) -0.0028(5) 0.0023(5) -0.0031(5) C10P 0.0245(6) 0.0495(8) 0.0272(6) -0.0065(6) -0.0041(5) 0.0050(6) C11P 0.0370(7) 0.0411(8) 0.0220(6) 0.0015(5) -0.0023(5) 0.0053(6) C12P 0.0307(6) 0.0332(7) 0.0250(6) 0.0012(5) -0.0012(5) -0.0015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.4283(13) . ? O1 C6 1.4214(13) . ? C2 C1P 1.5090(16) . ? C2 C3 1.5360(16) . ? C2 H2A 1.0000 . ? C3 C4 1.4965(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O4 1.2126(14) . ? C4 C5 1.5223(16) . ? C5 C51 1.5064(17) . ? C5 C6 1.5519(16) . ? C5 H5A 1.0000 . ? C6 C7P 1.5080(16) . ? C6 H6A 1.0000 . ? C51 O51 1.2003(14) . ? C51 O52 1.3334(16) . ? O52 C52 1.4485(15) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C1P C2P 1.3905(17) . ? C1P C6P 1.3913(16) . ? C2P C3P 1.3838(17) . ? C2P H2PA 0.9500 . ? C3P C4P 1.3841(18) . ? C3P H3PA 0.9500 . ? C4P C5P 1.3840(18) . ? C4P H4PA 0.9500 . ? C5P C6P 1.3878(17) . ? C5P H5PA 0.9500 . ? C6P H6PA 0.9500 . ? C7P C8P 1.3918(16) . ? C7P C12P 1.3940(16) . ? C8P C9P 1.3835(17) . ? C8P H8PA 0.9500 . ? C9P C10P 1.3833(18) . ? C9P H9PA 0.9500 . ? C10P C11P 1.3849(18) . ? C10P H10A 0.9500 . ? C11P C12P 1.3846(17) . ? C11P H11A 0.9500 . ? C12P H12A 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 C6 O1 C2 112.11(8) . . ? O1 C2 C1P 108.90(9) . . ? O1 C2 C3 109.90(9) . . ? C1P C2 C3 111.87(9) . . ? O1 C2 H2A 108.7 . . ? C1P C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C4 C3 C2 111.55(9) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? O4 C4 C3 123.68(11) . . ? O4 C4 C5 121.76(11) . . ? C3 C4 C5 114.54(10) . . ? C51 C5 C4 111.95(10) . . ? C51 C5 C6 112.39(9) . . ? C4 C5 C6 111.54(9) . . ? C51 C5 H5A 106.9 . . ? C4 C5 H5A 106.9 . . ? C6 C5 H5A 106.9 . . ? O1 C6 C7P 108.83(9) . . ? O1 C6 C5 109.30(9) . . ? C7P C6 C5 110.49(9) . . ? O1 C6 H6A 109.4 . . ? C7P C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? O51 C51 O52 124.23(12) . . ? O51 C51 C5 124.86(12) . . ? O52 C51 C5 110.90(10) . . ? C51 O52 C52 116.18(11) . . ? O52 C52 H52A 109.5 . . ? O52 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O52 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C2P C1P C6P 119.21(11) . . ? C2P C1P C2 118.85(10) . . ? C6P C1P C2 121.94(10) . . ? C3P C2P C1P 120.29(11) . . ? C3P C2P H2PA 119.9 . . ? C1P C2P H2PA 119.9 . . ? C4P C3P C2P 120.41(12) . . ? C4P C3P H3PA 119.8 . . ? C2P C3P H3PA 119.8 . . ? C3P C4P C5P 119.58(12) . . ? C3P C4P H4PA 120.2 . . ? C5P C4P H4PA 120.2 . . ? C4P C5P C6P 120.30(11) . . ? C4P C5P H5PA 119.8 . . ? C6P C5P H5PA 119.8 . . ? C5P C6P C1P 120.19(11) . . ? C5P C6P H6PA 119.9 . . ? C1P C6P H6PA 119.9 . . ? C8P C7P C12P 118.97(11) . . ? C8P C7P C6 120.02(10) . . ? C12P C7P C6 120.95(11) . . ? C9P C8P C7P 120.55(11) . . ? C9P C8P H8PA 119.7 . . ? C7P C8P H8PA 119.7 . . ? C10P C9P C8P 120.20(12) . . ? C10P C9P H9PA 119.9 . . ? C8P C9P H9PA 119.9 . . ? C9P C10P C11P 119.69(11) . . ? C9P C10P H10A 120.2 . . ? C11P C10P H10A 120.2 . . ? C12P C11P C10P 120.38(12) . . ? C12P C11P H11A 119.8 . . ? C10P C11P H11A 119.8 . . ? C11P C12P C7P 120.22(12) . . ? C11P C12P H12A 119.9 . . ? C7P C12P H12A 119.9 . . ? 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 C6 O1 C2 C1P 171.54(9) . . . . ? C6 O1 C2 C3 -65.59(11) . . . . ? O1 C2 C3 C4 52.98(12) . . . . ? C1P C2 C3 C4 174.07(9) . . . . ? C2 C3 C4 O4 137.80(12) . . . . ? C2 C3 C4 C5 -43.58(13) . . . . ? O4 C4 C5 C51 -11.37(16) . . . . ? C3 C4 C5 C51 169.98(10) . . . . ? O4 C4 C5 C6 -138.28(11) . . . . ? C3 C4 C5 C6 43.07(13) . . . . ? C2 O1 C6 C7P -174.64(9) . . . . ? C2 O1 C6 C5 64.62(11) . . . . ? C51 C5 C6 O1 -178.29(9) . . . . ? C4 C5 C6 O1 -51.62(12) . . . . ? C51 C5 C6 C7P 61.98(12) . . . . ? C4 C5 C6 C7P -171.35(9) . . . . ? C4 C5 C51 O51 112.01(13) . . . . ? C6 C5 C51 O51 -121.55(13) . . . . ? C4 C5 C51 O52 -69.18(12) . . . . ? C6 C5 C51 O52 57.27(13) . . . . ? O51 C51 O52 C52 0.96(18) . . . . ? C5 C51 O52 C52 -177.86(10) . . . . ? O1 C2 C1P C2P -166.74(10) . . . . ? C3 C2 C1P C2P 71.58(13) . . . . ? O1 C2 C1P C6P 12.49(14) . . . . ? C3 C2 C1P C6P -109.18(12) . . . . ? C6P C1P C2P C3P -0.41(18) . . . . ? C2 C1P C2P C3P 178.84(11) . . . . ? C1P C2P C3P C4P -0.84(19) . . . . ? C2P C3P C4P C5P 1.21(19) . . . . ? C3P C4P C5P C6P -0.34(19) . . . . ? C4P C5P C6P C1P -0.91(18) . . . . ? C2P C1P C6P C5P 1.28(17) . . . . ? C2 C1P C6P C5P -177.95(11) . . . . ? O1 C6 C7P C8P 148.37(10) . . . . ? C5 C6 C7P C8P -91.62(12) . . . . ? O1 C6 C7P C12P -34.50(14) . . . . ? C5 C6 C7P C12P 85.51(13) . . . . ? C12P C7P C8P C9P 0.52(18) . . . . ? C6 C7P C8P C9P 177.71(11) . . . . ? C7P C8P C9P C10P -0.06(18) . . . . ? C8P C9P C10P C11P -0.63(19) . . . . ? C9P C10P C11P C12P 0.86(19) . . . . ? C10P C11P C12P C7P -0.39(18) . . . . ? C8P C7P C12P C11P -0.30(18) . . . . ? C6 C7P C12P C11P -177.46(11) . . . . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.28 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.04 #===END of CIF data_6b _database_code_depnum_ccdc_archive 'CCDC 250777' # PHACOH #5199 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 O4' _chemical_formula_sum 'C19 H18 O4' _chemical_formula_weight 310.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5429(5) _cell_length_b 9.5351(8) _cell_length_c 15.1955(13) _cell_angle_alpha 82.937(2) _cell_angle_beta 85.273(2) _cell_angle_gamma 77.190(2) _cell_volume 775.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2953 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 7088 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.035 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3507 _reflns_number_gt 2913 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _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^)+(0.059P)^2^+0.028P] 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 3507 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.111 _refine_ls_wR_factor_gt 0.107 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_restrained_S_all 1.09 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.23095(14) 0.45429(8) 0.73671(5) 0.0239(2) Uani 1 1 d . . . C2 C 0.2794(2) 0.33865(12) 0.80772(7) 0.0238(3) Uani 1 1 d . . . H2 H 0.4360 0.3463 0.8333 0.029 Uiso 1 1 calc R . . C3 C 0.0796(2) 0.35714(12) 0.88215(7) 0.0261(3) Uani 1 1 d . . . C4 C -0.1386(2) 0.45142(13) 0.87004(8) 0.0266(3) Uani 1 1 d . . . C5 C -0.1962(2) 0.53944(13) 0.78324(8) 0.0265(3) Uani 1 1 d . . . H5A H -0.1858 0.6407 0.7875 0.032 Uiso 1 1 calc R . . H5B H -0.3677 0.5394 0.7694 0.032 Uiso 1 1 calc R . . C6 C -0.0165(2) 0.47942(12) 0.70875(7) 0.0226(2) Uani 1 1 d . . . H6 H -0.0522 0.3859 0.6960 0.027 Uiso 1 1 calc R . . C7 C -0.0434(2) 0.58455(12) 0.62565(7) 0.0219(2) Uani 1 1 d . . . C8 C -0.2287(2) 0.58579(13) 0.56939(8) 0.0272(3) Uani 1 1 d . . . H8 H -0.3316 0.5175 0.5820 0.033 Uiso 1 1 calc R . . C9 C -0.2650(2) 0.68606(14) 0.49477(8) 0.0315(3) Uani 1 1 d . . . H9 H -0.3927 0.6862 0.4567 0.038 Uiso 1 1 calc R . . C10 C -0.1155(2) 0.78593(14) 0.47569(8) 0.0327(3) Uani 1 1 d . . . H10 H -0.1400 0.8545 0.4246 0.039 Uiso 1 1 calc R . . C11 C 0.0696(2) 0.78496(14) 0.53160(8) 0.0321(3) Uani 1 1 d . . . H11 H 0.1725 0.8532 0.5188 0.038 Uiso 1 1 calc R . . C12 C 0.1060(2) 0.68502(12) 0.60625(8) 0.0273(3) Uani 1 1 d . . . H12 H 0.2336 0.6852 0.6443 0.033 Uiso 1 1 calc R . . C13 C 0.3324(2) 0.19252(12) 0.77059(7) 0.0226(2) Uani 1 1 d . . . C14 C 0.5473(2) 0.15643(13) 0.71664(8) 0.0280(3) Uani 1 1 d . . . H14 H 0.6544 0.2225 0.7044 0.034 Uiso 1 1 calc R . . C15 C 0.6077(2) 0.02610(14) 0.68059(8) 0.0321(3) Uani 1 1 d . . . H15 H 0.7548 0.0034 0.6437 0.039 Uiso 1 1 calc R . . C16 C 0.4536(2) -0.07139(13) 0.69837(8) 0.0315(3) Uani 1 1 d . . . H16 H 0.4949 -0.1613 0.6739 0.038 Uiso 1 1 calc R . . C17 C 0.2397(2) -0.03732(13) 0.75185(8) 0.0313(3) Uani 1 1 d . . . H17 H 0.1337 -0.1040 0.7642 0.038 Uiso 1 1 calc R . . C18 C 0.1786(2) 0.09441(13) 0.78780(8) 0.0267(3) Uani 1 1 d . . . H18 H 0.0308 0.1173 0.8243 0.032 Uiso 1 1 calc R . . C19 C 0.1323(3) 0.28397(13) 0.97061(8) 0.0323(3) Uani 1 1 d . . . O20 O 0.36500(18) 0.20706(10) 0.97521(6) 0.0379(2) Uani 1 1 d . . . C21 C 0.4426(3) 0.14399(16) 1.06276(9) 0.0492(4) Uani 1 1 d . . . H21A H 0.6149 0.0902 1.0581 0.074 Uiso 1 1 calc R . . H21B H 0.3360 0.0781 1.0882 0.074 Uiso 1 1 calc R . . H21C H 0.4295 0.2210 1.1012 0.074 Uiso 1 1 calc R . . O22 O -0.0171(2) 0.29259(11) 1.03505(6) 0.0422(3) Uani 1 1 d . . . O23 O -0.32058(17) 0.47959(10) 0.93325(6) 0.0350(2) Uani 1 1 d . . . H23 H -0.2757 0.4314 0.9814 0.052 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 0.0233(4) 0.0226(4) 0.0247(4) 0.0020(3) -0.0047(3) -0.0041(3) C2 0.0270(6) 0.0217(6) 0.0221(6) 0.0002(4) -0.0066(5) -0.0039(4) C3 0.0354(7) 0.0225(6) 0.0202(6) -0.0024(4) -0.0033(5) -0.0049(5) C4 0.0333(7) 0.0251(6) 0.0217(6) -0.0041(5) 0.0027(5) -0.0076(5) C5 0.0258(6) 0.0263(6) 0.0247(6) -0.0004(5) 0.0002(5) -0.0020(5) C6 0.0221(6) 0.0233(6) 0.0223(6) -0.0016(4) -0.0032(4) -0.0044(4) C7 0.0223(6) 0.0210(6) 0.0201(5) -0.0033(4) 0.0008(4) -0.0002(4) C8 0.0259(6) 0.0281(6) 0.0269(6) -0.0026(5) -0.0022(5) -0.0040(5) C9 0.0300(7) 0.0365(7) 0.0252(6) -0.0023(5) -0.0070(5) 0.0001(5) C10 0.0369(7) 0.0297(7) 0.0241(6) 0.0050(5) 0.0014(5) 0.0029(5) C11 0.0329(7) 0.0275(6) 0.0333(7) 0.0036(5) 0.0025(5) -0.0066(5) C12 0.0274(6) 0.0261(6) 0.0278(6) -0.0010(5) -0.0034(5) -0.0049(5) C13 0.0249(6) 0.0221(6) 0.0193(5) 0.0005(4) -0.0076(4) -0.0012(4) C14 0.0253(6) 0.0283(6) 0.0300(6) -0.0012(5) -0.0040(5) -0.0049(5) C15 0.0286(7) 0.0332(7) 0.0311(7) -0.0058(5) -0.0024(5) 0.0022(5) C16 0.0388(7) 0.0229(6) 0.0315(7) -0.0063(5) -0.0126(5) 0.0021(5) C17 0.0365(7) 0.0254(6) 0.0338(7) -0.0010(5) -0.0101(5) -0.0088(5) C18 0.0267(6) 0.0269(6) 0.0261(6) -0.0017(5) -0.0046(5) -0.0040(5) C19 0.0495(8) 0.0233(6) 0.0241(6) -0.0032(5) -0.0055(6) -0.0062(5) O20 0.0549(6) 0.0290(5) 0.0247(5) -0.0006(4) -0.0127(4) 0.0046(4) C21 0.0781(11) 0.0362(8) 0.0267(7) 0.0009(6) -0.0198(7) 0.0056(7) O22 0.0596(7) 0.0418(6) 0.0225(5) 0.0005(4) 0.0011(4) -0.0084(5) O23 0.0406(5) 0.0365(5) 0.0234(5) -0.0013(4) 0.0070(4) -0.0032(4) _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 C2 1.4408(13) . ? O1 C6 1.4300(13) . ? C2 C3 1.5142(16) . ? C2 C13 1.5267(16) . ? C2 H2 1.0000 . ? C3 C4 1.3484(18) . ? C3 C19 1.4569(16) . ? C4 O23 1.3402(14) . ? C4 C5 1.4915(16) . ? C5 C6 1.5237(16) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5084(15) . ? C6 H6 1.0000 . ? C7 C8 1.3863(16) . ? C7 C12 1.3902(16) . ? C8 C9 1.3878(17) . ? C8 H8 0.9500 . ? C9 C10 1.3854(18) . ? C9 H9 0.9500 . ? C10 C11 1.3828(19) . ? C10 H10 0.9500 . ? C11 C12 1.3864(16) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.3882(16) . ? C13 C14 1.3917(16) . ? C14 C15 1.3817(17) . ? C14 H14 0.9500 . ? C15 C16 1.3855(18) . ? C15 H15 0.9500 . ? C16 C17 1.3811(18) . ? C16 H16 0.9500 . ? C17 C18 1.3930(17) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 O22 1.2277(16) . ? C19 O20 1.3377(17) . ? O20 C21 1.4489(15) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? O23 H23 0.8400 . ? 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 C6 O1 C2 112.35(8) . . ? O1 C2 C3 111.69(9) . . ? O1 C2 C13 110.12(9) . . ? C3 C2 C13 115.15(9) . . ? O1 C2 H2 106.4 . . ? C3 C2 H2 106.4 . . ? C13 C2 H2 106.4 . . ? C4 C3 C19 119.14(11) . . ? C4 C3 C2 120.84(10) . . ? C19 C3 C2 119.70(11) . . ? O23 C4 C3 124.79(11) . . ? O23 C4 C5 113.15(10) . . ? C3 C4 C5 122.03(11) . . ? C4 C5 C6 111.09(10) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? O1 C6 C7 109.70(9) . . ? O1 C6 C5 108.91(9) . . ? C7 C6 C5 110.56(9) . . ? O1 C6 H6 109.2 . . ? C7 C6 H6 109.2 . . ? C5 C6 H6 109.2 . . ? C8 C7 C12 119.10(10) . . ? C8 C7 C6 119.39(10) . . ? C12 C7 C6 121.44(10) . . ? C7 C8 C9 120.52(11) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 120.16(11) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.49(11) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.45(11) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 120.27(11) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C18 C13 C14 118.57(11) . . ? C18 C13 C2 123.64(10) . . ? C14 C13 C2 117.79(10) . . ? C15 C14 C13 121.12(11) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 119.92(12) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C17 C16 C15 119.70(11) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.28(11) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C13 C18 C17 120.41(11) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? O22 C19 O20 122.81(12) . . ? O22 C19 C3 124.46(13) . . ? O20 C19 C3 112.72(11) . . ? C19 O20 C21 116.53(11) . . ? O20 C21 H21A 109.5 . . ? O20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C4 O23 H23 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 C6 O1 C2 C3 -49.52(12) . . . . ? C6 O1 C2 C13 79.74(11) . . . . ? O1 C2 C3 C4 14.46(15) . . . . ? C13 C2 C3 C4 -112.11(12) . . . . ? O1 C2 C3 C19 -158.99(10) . . . . ? C13 C2 C3 C19 74.44(14) . . . . ? C19 C3 C4 O23 -3.20(19) . . . . ? C2 C3 C4 O23 -176.69(10) . . . . ? C19 C3 C4 C5 174.69(11) . . . . ? C2 C3 C4 C5 1.21(18) . . . . ? O23 C4 C5 C6 -166.26(10) . . . . ? C3 C4 C5 C6 15.62(16) . . . . ? C2 O1 C6 C7 -171.21(8) . . . . ? C2 O1 C6 C5 67.67(11) . . . . ? C4 C5 C6 O1 -48.24(12) . . . . ? C4 C5 C6 C7 -168.83(9) . . . . ? O1 C6 C7 C8 156.84(10) . . . . ? C5 C6 C7 C8 -83.04(13) . . . . ? O1 C6 C7 C12 -26.23(14) . . . . ? C5 C6 C7 C12 93.89(13) . . . . ? C12 C7 C8 C9 -0.12(17) . . . . ? C6 C7 C8 C9 176.89(11) . . . . ? C7 C8 C9 C10 0.15(18) . . . . ? C8 C9 C10 C11 -0.09(19) . . . . ? C9 C10 C11 C12 0.00(19) . . . . ? C10 C11 C12 C7 0.03(18) . . . . ? C8 C7 C12 C11 0.03(17) . . . . ? C6 C7 C12 C11 -176.92(11) . . . . ? O1 C2 C13 C18 -113.62(11) . . . . ? C3 C2 C13 C18 13.74(15) . . . . ? O1 C2 C13 C14 66.46(12) . . . . ? C3 C2 C13 C14 -166.18(10) . . . . ? C18 C13 C14 C15 0.08(17) . . . . ? C2 C13 C14 C15 -179.99(11) . . . . ? C13 C14 C15 C16 -0.30(18) . . . . ? C14 C15 C16 C17 0.24(18) . . . . ? C15 C16 C17 C18 0.04(18) . . . . ? C14 C13 C18 C17 0.20(16) . . . . ? C2 C13 C18 C17 -179.72(11) . . . . ? C16 C17 C18 C13 -0.26(18) . . . . ? C4 C3 C19 O22 6.3(2) . . . . ? C2 C3 C19 O22 179.82(11) . . . . ? C4 C3 C19 O20 -172.63(11) . . . . ? C2 C3 C19 O20 0.93(16) . . . . ? O22 C19 O20 C21 -5.69(18) . . . . ? C3 C19 O20 C21 173.21(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O23 H23 O22 0.84 1.89 2.6121(13) 144 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.30 _refine_diff_density_min -0.21 _refine_diff_density_rms 0.04