# 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 _publ_contact_author_name 'Hu, Wenhao' _publ_contact_author_email whu@chem.ecnu.edu.cn _publ_section_title ; Diastereoselective Three-component Reactions of Aryldiazoacetates with Alcohols/Water and Alkynals: Application to Substituted Enelactones ; loop_ _publ_author_name 'Xingchun Han' 'Liqing Jiang' 'Min Tang' 'Wenhao Hu' data_cd201266 _database_code_depnum_ccdc_archive 'CCDC 806582' #TrackingRef 'web_deposit_cif_file_0_XingchunHan_1294217356.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9167(17) _cell_length_b 9.8437(13) _cell_length_c 13.3798(17) _cell_angle_alpha 90.00 _cell_angle_beta 107.208(2) _cell_angle_gamma 90.00 _cell_volume 1625.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2138 _cell_measurement_theta_min 5.223 _cell_measurement_theta_max 55.285 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.390 _exptl_crystal_size_mid 0.301 _exptl_crystal_size_min 0.127 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7405 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8645 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3180 _reflns_number_gt 2204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0508P)^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 3180 _refine_ls_number_parameters 213 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.51451(8) 0.52548(10) 0.26029(8) 0.0354(3) Uani 1 1 d . . . O2 O 0.76370(9) 0.34589(14) 0.25353(11) 0.0524(4) Uani 1 1 d D . . O3 O 0.57213(9) 0.33651(13) 0.07789(9) 0.0513(4) Uani 1 1 d . . . O4 O 0.42899(9) 0.30139(14) 0.13399(9) 0.0558(4) Uani 1 1 d . . . C1 C 0.57904(11) 0.41185(16) 0.25155(11) 0.0308(4) Uani 1 1 d . . . C2 C 0.69577(11) 0.45763(16) 0.25608(12) 0.0357(4) Uani 1 1 d . . . H2 H 0.6915 0.5161 0.1957 0.043 Uiso 1 1 calc R . . C3 C 0.74508(13) 0.53446(17) 0.35146(13) 0.0407(4) Uani 1 1 d . . . C4 C 0.78278(16) 0.5959(2) 0.42770(15) 0.0612(6) Uani 1 1 d . . . H4 H 0.8130 0.6450 0.4887 0.073 Uiso 1 1 calc R . . C5 C 0.52834(13) 0.34484(16) 0.14465(12) 0.0358(4) Uani 1 1 d . . . C6 C 0.37433(17) 0.2362(2) 0.03560(16) 0.0767(7) Uani 1 1 d . . . H6A H 0.3573 0.3027 -0.0193 0.115 Uiso 1 1 calc R . . H6B H 0.3087 0.1945 0.0402 0.115 Uiso 1 1 calc R . . H6C H 0.4208 0.1680 0.0206 0.115 Uiso 1 1 calc R . . C7 C 0.58112(11) 0.31574(16) 0.34074(12) 0.0313(4) Uani 1 1 d . . . C8 C 0.59840(13) 0.17806(17) 0.33245(13) 0.0417(4) Uani 1 1 d . . . H8 H 0.6057 0.1430 0.2704 0.050 Uiso 1 1 calc R . . C9 C 0.60483(15) 0.09268(19) 0.41560(15) 0.0533(5) Uani 1 1 d . . . H9 H 0.6170 0.0004 0.4094 0.064 Uiso 1 1 calc R . . C10 C 0.59348(15) 0.1425(2) 0.50719(15) 0.0559(5) Uani 1 1 d . . . H10 H 0.5972 0.0843 0.5629 0.067 Uiso 1 1 calc R . . C11 C 0.57657(14) 0.2793(2) 0.51635(13) 0.0491(5) Uani 1 1 d . . . H11 H 0.5692 0.3138 0.5786 0.059 Uiso 1 1 calc R . . C12 C 0.57055(12) 0.36546(17) 0.43373(12) 0.0386(4) Uani 1 1 d . . . H12 H 0.5593 0.4579 0.4406 0.046 Uiso 1 1 calc R . . C13 C 0.50258(13) 0.62800(17) 0.18123(13) 0.0427(4) Uani 1 1 d . . . H13A H 0.4896 0.5857 0.1131 0.051 Uiso 1 1 calc R . . H13B H 0.5684 0.6815 0.1954 0.051 Uiso 1 1 calc R . . C14 C 0.40921(12) 0.71731(17) 0.18180(12) 0.0358(4) Uani 1 1 d . . . C15 C 0.42478(14) 0.85237(18) 0.20707(13) 0.0469(5) Uani 1 1 d . . . H15 H 0.4944 0.8886 0.2249 0.056 Uiso 1 1 calc R . . C16 C 0.33840(18) 0.9349(2) 0.20627(15) 0.0612(6) Uani 1 1 d . . . H16 H 0.3500 1.0263 0.2236 0.073 Uiso 1 1 calc R . . C17 C 0.23632(18) 0.8834(2) 0.18025(16) 0.0650(6) Uani 1 1 d . . . H17 H 0.1781 0.9392 0.1798 0.078 Uiso 1 1 calc R . . C18 C 0.21956(15) 0.7491(2) 0.15467(16) 0.0651(6) Uani 1 1 d . . . H18 H 0.1498 0.7135 0.1370 0.078 Uiso 1 1 calc R . . C19 C 0.30530(14) 0.66637(18) 0.15488(15) 0.0519(5) Uani 1 1 d . . . H19 H 0.2931 0.5753 0.1367 0.062 Uiso 1 1 calc R . . H2A H 0.735(2) 0.309(2) 0.1938(15) 0.106(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0395(6) 0.0370(6) 0.0314(6) 0.0069(5) 0.0131(5) 0.0101(5) O2 0.0354(7) 0.0620(9) 0.0573(9) -0.0066(7) 0.0099(6) 0.0096(6) O3 0.0471(7) 0.0759(10) 0.0325(7) -0.0084(6) 0.0141(6) 0.0038(6) O4 0.0416(7) 0.0823(10) 0.0397(7) -0.0081(7) 0.0060(6) -0.0182(7) C1 0.0299(8) 0.0335(9) 0.0278(8) 0.0011(7) 0.0067(6) 0.0043(7) C2 0.0311(8) 0.0416(10) 0.0338(9) 0.0018(7) 0.0086(7) 0.0027(7) C3 0.0406(9) 0.0429(10) 0.0364(10) 0.0064(8) 0.0078(8) -0.0074(8) C4 0.0763(14) 0.0600(13) 0.0424(12) -0.0015(10) 0.0102(10) -0.0263(11) C5 0.0349(9) 0.0394(10) 0.0308(9) 0.0046(7) 0.0062(7) 0.0055(7) C6 0.0609(13) 0.1054(19) 0.0506(13) -0.0199(13) -0.0042(10) -0.0286(13) C7 0.0269(8) 0.0368(9) 0.0287(9) 0.0021(7) 0.0059(6) 0.0013(7) C8 0.0468(10) 0.0390(10) 0.0373(10) -0.0006(8) 0.0092(8) 0.0007(8) C9 0.0638(12) 0.0375(10) 0.0530(13) 0.0080(9) 0.0086(10) 0.0009(9) C10 0.0642(12) 0.0560(13) 0.0447(12) 0.0186(10) 0.0116(10) -0.0065(10) C11 0.0565(11) 0.0602(13) 0.0325(10) 0.0050(9) 0.0161(8) -0.0037(10) C12 0.0400(9) 0.0414(10) 0.0344(10) 0.0016(8) 0.0110(8) 0.0025(8) C13 0.0452(10) 0.0437(10) 0.0416(10) 0.0131(8) 0.0165(8) 0.0079(8) C14 0.0402(9) 0.0380(10) 0.0294(9) 0.0094(7) 0.0103(7) 0.0064(8) C15 0.0517(11) 0.0468(12) 0.0384(10) -0.0018(8) 0.0073(8) 0.0008(9) C16 0.0867(16) 0.0458(12) 0.0516(12) -0.0030(10) 0.0211(11) 0.0174(11) C17 0.0645(14) 0.0718(16) 0.0650(14) 0.0178(12) 0.0287(11) 0.0332(12) C18 0.0416(11) 0.0726(16) 0.0822(16) 0.0255(13) 0.0199(11) 0.0117(10) C19 0.0471(11) 0.0420(11) 0.0654(13) 0.0122(9) 0.0148(9) 0.0030(9) _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 1.4203(17) . ? O1 C13 1.4369(18) . ? O2 C2 1.4137(19) . ? O2 H2A 0.855(16) . ? O3 C5 1.1931(18) . ? O4 C5 1.3198(18) . ? O4 C6 1.447(2) . ? C1 C7 1.517(2) . ? C1 C5 1.535(2) . ? C1 C2 1.558(2) . ? C2 C3 1.458(2) . ? C2 H2 0.9800 . ? C3 C4 1.162(2) . ? C4 H4 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C12 1.381(2) . ? C7 C8 1.383(2) . ? C8 C9 1.377(2) . ? C8 H8 0.9300 . ? C9 C10 1.367(3) . ? C9 H9 0.9300 . ? C10 C11 1.376(3) . ? C10 H10 0.9300 . ? C11 C12 1.377(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.494(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.372(2) . ? C14 C19 1.377(2) . ? C15 C16 1.378(2) . ? C15 H15 0.9300 . ? C16 C17 1.359(3) . ? C16 H16 0.9300 . ? C17 C18 1.367(3) . ? C17 H17 0.9300 . ? C18 C19 1.374(2) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C13 115.48(11) . . ? C2 O2 H2A 104.7(17) . . ? C5 O4 C6 116.06(14) . . ? O1 C1 C7 107.50(11) . . ? O1 C1 C5 108.44(11) . . ? C7 C1 C5 111.62(13) . . ? O1 C1 C2 110.72(12) . . ? C7 C1 C2 110.98(11) . . ? C5 C1 C2 107.57(12) . . ? O2 C2 C3 108.14(13) . . ? O2 C2 C1 112.00(13) . . ? C3 C2 C1 110.57(13) . . ? O2 C2 H2 108.7 . . ? C3 C2 H2 108.7 . . ? C1 C2 H2 108.7 . . ? C4 C3 C2 178.93(19) . . ? C3 C4 H4 180.0 . . ? O3 C5 O4 123.91(15) . . ? O3 C5 C1 124.15(14) . . ? O4 C5 C1 111.91(13) . . ? O4 C6 H6A 109.5 . . ? O4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 118.74(15) . . ? C12 C7 C1 120.29(14) . . ? C8 C7 C1 120.91(14) . . ? C9 C8 C7 120.38(16) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.55(17) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 119.53(17) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.27(17) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.53(16) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? O1 C13 C14 108.69(12) . . ? O1 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? O1 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.3 . . ? C15 C14 C19 118.54(16) . . ? C15 C14 C13 120.78(15) . . ? C19 C14 C13 120.67(16) . . ? C14 C15 C16 120.69(18) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 120.27(19) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.68(18) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C19 120.32(19) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 120.50(18) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? 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 C13 O1 C1 C7 -179.63(12) . . . . ? C13 O1 C1 C5 -58.80(16) . . . . ? C13 O1 C1 C2 58.99(15) . . . . ? O1 C1 C2 O2 176.66(12) . . . . ? C7 C1 C2 O2 57.35(17) . . . . ? C5 C1 C2 O2 -65.02(16) . . . . ? O1 C1 C2 C3 55.98(16) . . . . ? C7 C1 C2 C3 -63.33(17) . . . . ? C5 C1 C2 C3 174.30(13) . . . . ? O2 C2 C3 C4 -137(10) . . . . ? C1 C2 C3 C4 -14(10) . . . . ? C6 O4 C5 O3 2.2(2) . . . . ? C6 O4 C5 C1 -179.84(15) . . . . ? O1 C1 C5 O3 117.13(17) . . . . ? C7 C1 C5 O3 -124.63(16) . . . . ? C2 C1 C5 O3 -2.7(2) . . . . ? O1 C1 C5 O4 -60.80(16) . . . . ? C7 C1 C5 O4 57.44(17) . . . . ? C2 C1 C5 O4 179.41(13) . . . . ? O1 C1 C7 C12 -28.77(18) . . . . ? C5 C1 C7 C12 -147.57(14) . . . . ? C2 C1 C7 C12 92.45(16) . . . . ? O1 C1 C7 C8 154.13(13) . . . . ? C5 C1 C7 C8 35.33(18) . . . . ? C2 C1 C7 C8 -84.65(17) . . . . ? C12 C7 C8 C9 0.0(2) . . . . ? C1 C7 C8 C9 177.16(15) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C7 0.1(2) . . . . ? C8 C7 C12 C11 -0.3(2) . . . . ? C1 C7 C12 C11 -177.49(14) . . . . ? C1 O1 C13 C14 163.55(12) . . . . ? O1 C13 C14 C15 116.19(17) . . . . ? O1 C13 C14 C19 -65.1(2) . . . . ? C19 C14 C15 C16 0.5(3) . . . . ? C13 C14 C15 C16 179.18(15) . . . . ? C14 C15 C16 C17 -0.1(3) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? C17 C18 C19 C14 0.6(3) . . . . ? C15 C14 C19 C18 -0.8(3) . . . . ? C13 C14 C19 C18 -179.47(16) . . . . ? 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 O2 H2A O3 0.855(16) 2.23(2) 2.8659(17) 131(2) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.167 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 # Attachment 'web_deposit_cif_file_0_XingchunHan_1294218208.cif' data_cd201646 _database_code_depnum_ccdc_archive 'CCDC 806589' #TrackingRef 'web_deposit_cif_file_0_XingchunHan_1294218208.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 O4' _chemical_formula_weight 220.22 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 C2/c 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' '-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 10.4347(8) _cell_length_b 15.9131(12) _cell_length_c 14.1048(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.4870(10) _cell_angle_gamma 90.00 _cell_volume 2207.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3653 _cell_measurement_theta_min 4.868 _cell_measurement_theta_max 56.224 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.412 _exptl_crystal_size_mid 0.369 _exptl_crystal_size_min 0.315 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5979 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5925 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2171 _reflns_number_gt 1905 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.6167P] 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 SHELXL _refine_ls_extinction_coef 0.0084(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2171 _refine_ls_number_parameters 155 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.013 _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 0.36269(10) 0.33106(6) 0.08728(8) 0.0418(3) Uani 1 1 d D . . O2 O 0.08464(11) 0.28447(7) 0.05135(8) 0.0491(3) Uani 1 1 d D . . O3 O 0.35668(12) 0.31233(7) 0.27168(8) 0.0575(3) Uani 1 1 d . . . O4 O 0.17860(12) 0.39809(6) 0.24518(8) 0.0513(3) Uani 1 1 d . . . C1 C 0.27144(13) 0.38403(8) 0.11314(9) 0.0351(3) Uani 1 1 d . . . C2 C 0.12833(14) 0.36597(8) 0.03722(10) 0.0381(3) Uani 1 1 d . . . H2 H 0.0647 0.4065 0.0492 0.046 Uiso 1 1 calc R . . C3 C 0.13051(15) 0.37892(9) -0.06541(11) 0.0446(4) Uani 1 1 d . . . C4 C 0.1366(2) 0.38581(13) -0.14634(12) 0.0653(5) Uani 1 1 d . . . H4 H 0.1414 0.3913 -0.2107 0.078 Uiso 1 1 calc R . . C5 C 0.31060(14) 0.47653(8) 0.11223(9) 0.0359(3) Uani 1 1 d . . . C6 C 0.43697(16) 0.49773(9) 0.10698(12) 0.0467(4) Uani 1 1 d . . . H6 H 0.4973 0.4557 0.1038 0.056 Uiso 1 1 calc R . . C7 C 0.47369(18) 0.58128(11) 0.10643(14) 0.0606(5) Uani 1 1 d . . . H7 H 0.5588 0.5949 0.1031 0.073 Uiso 1 1 calc R . . C8 C 0.3857(2) 0.64418(10) 0.11073(14) 0.0634(5) Uani 1 1 d . . . H8 H 0.4111 0.7002 0.1103 0.076 Uiso 1 1 calc R . . C9 C 0.2599(2) 0.62395(9) 0.11561(14) 0.0570(5) Uani 1 1 d . . . H9 H 0.1998 0.6664 0.1180 0.068 Uiso 1 1 calc R . . C10 C 0.22264(16) 0.54085(9) 0.11691(11) 0.0450(4) Uani 1 1 d . . . H10 H 0.1378 0.5277 0.1210 0.054 Uiso 1 1 calc R . . C11 C 0.27420(15) 0.35931(8) 0.21946(10) 0.0398(3) Uani 1 1 d . . . C12 C 0.1790(2) 0.38375(13) 0.34678(13) 0.0669(5) Uani 1 1 d . . . H12A H 0.1948 0.3252 0.3631 0.100 Uiso 1 1 calc R . . H12B H 0.0927 0.3999 0.3515 0.100 Uiso 1 1 calc R . . H12C H 0.2498 0.4166 0.3930 0.100 Uiso 1 1 calc R . . H1 H 0.4135(19) 0.3107(12) 0.1374(12) 0.064(6) Uiso 1 1 d D . . H2A H 0.126(2) 0.2503(12) 0.0254(16) 0.085(7) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0452(6) 0.0417(5) 0.0400(5) -0.0029(4) 0.0164(5) 0.0090(4) O2 0.0545(7) 0.0441(6) 0.0563(7) -0.0066(5) 0.0286(5) -0.0140(5) O3 0.0605(7) 0.0653(7) 0.0479(6) 0.0166(5) 0.0196(5) 0.0089(5) O4 0.0642(7) 0.0560(6) 0.0446(6) 0.0041(5) 0.0328(5) 0.0046(5) C1 0.0379(7) 0.0359(6) 0.0352(7) -0.0017(5) 0.0172(5) 0.0008(5) C2 0.0392(7) 0.0388(7) 0.0388(7) -0.0021(5) 0.0163(6) -0.0023(5) C3 0.0413(8) 0.0493(8) 0.0410(8) -0.0002(6) 0.0106(6) -0.0009(6) C4 0.0672(12) 0.0902(13) 0.0381(8) 0.0052(8) 0.0171(8) -0.0002(9) C5 0.0416(7) 0.0383(7) 0.0312(6) -0.0018(5) 0.0165(5) -0.0030(5) C6 0.0453(9) 0.0479(8) 0.0523(8) -0.0023(6) 0.0236(7) -0.0030(6) C7 0.0589(10) 0.0596(10) 0.0736(11) -0.0050(8) 0.0357(9) -0.0198(8) C8 0.0854(14) 0.0405(8) 0.0754(11) -0.0067(7) 0.0417(10) -0.0167(8) C9 0.0758(12) 0.0382(8) 0.0682(11) -0.0034(7) 0.0388(9) 0.0009(7) C10 0.0508(9) 0.0408(7) 0.0511(8) -0.0018(6) 0.0271(7) -0.0005(6) C11 0.0460(8) 0.0377(7) 0.0377(7) -0.0012(5) 0.0167(6) -0.0065(6) C12 0.0899(14) 0.0763(12) 0.0498(10) 0.0022(8) 0.0436(10) -0.0042(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.4078(15) . ? O1 H1 0.797(15) . ? O2 C2 1.4108(16) . ? O2 H2A 0.847(16) . ? O3 C11 1.1913(17) . ? O4 C11 1.3226(17) . ? O4 C12 1.4497(18) . ? C1 C5 1.5287(17) . ? C1 C11 1.5413(17) . ? C1 C2 1.5467(19) . ? C2 C3 1.4698(19) . ? C2 H2 0.9800 . ? C3 C4 1.169(2) . ? C4 H4 0.9300 . ? C5 C6 1.387(2) . ? C5 C10 1.3910(19) . ? C6 C7 1.384(2) . ? C6 H6 0.9300 . ? C7 C8 1.373(3) . ? C7 H7 0.9300 . ? C8 C9 1.376(3) . ? C8 H8 0.9300 . ? C9 C10 1.380(2) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C1 O1 H1 108.7(14) . . ? C2 O2 H2A 107.2(15) . . ? C11 O4 C12 116.36(13) . . ? O1 C1 C5 111.62(10) . . ? O1 C1 C11 107.73(10) . . ? C5 C1 C11 109.62(10) . . ? O1 C1 C2 106.83(10) . . ? C5 C1 C2 111.85(11) . . ? C11 C1 C2 109.06(11) . . ? O2 C2 C3 112.32(11) . . ? O2 C2 C1 110.85(11) . . ? C3 C2 C1 109.10(11) . . ? O2 C2 H2 108.1 . . ? C3 C2 H2 108.1 . . ? C1 C2 H2 108.1 . . ? C4 C3 C2 176.61(18) . . ? C3 C4 H4 180.0 . . ? C6 C5 C10 118.53(13) . . ? C6 C5 C1 119.75(12) . . ? C10 C5 C1 121.71(12) . . ? C7 C6 C5 120.25(14) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 120.64(15) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 119.65(15) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C10 120.19(15) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 120.73(14) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? O3 C11 O4 125.36(13) . . ? O3 C11 C1 122.48(13) . . ? O4 C11 C1 112.14(12) . . ? O4 C12 H12A 109.5 . . ? O4 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O4 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 O2 67.76(13) . . . . ? C5 C1 C2 O2 -169.82(10) . . . . ? C11 C1 C2 O2 -48.41(14) . . . . ? O1 C1 C2 C3 -56.43(14) . . . . ? C5 C1 C2 C3 65.98(14) . . . . ? C11 C1 C2 C3 -172.61(11) . . . . ? O2 C2 C3 C4 -57(3) . . . . ? C1 C2 C3 C4 66(3) . . . . ? O1 C1 C5 C6 -12.36(17) . . . . ? C11 C1 C5 C6 106.92(14) . . . . ? C2 C1 C5 C6 -132.00(13) . . . . ? O1 C1 C5 C10 167.87(12) . . . . ? C11 C1 C5 C10 -72.85(16) . . . . ? C2 C1 C5 C10 48.24(17) . . . . ? C10 C5 C6 C7 0.0(2) . . . . ? C1 C5 C6 C7 -179.79(14) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C8 C9 C10 C5 -0.7(3) . . . . ? C6 C5 C10 C9 0.5(2) . . . . ? C1 C5 C10 C9 -179.76(14) . . . . ? C12 O4 C11 O3 2.3(2) . . . . ? C12 O4 C11 C1 -175.64(12) . . . . ? O1 C1 C11 O3 10.31(18) . . . . ? C5 C1 C11 O3 -111.34(15) . . . . ? C2 C1 C11 O3 125.91(14) . . . . ? O1 C1 C11 O4 -171.66(11) . . . . ? C5 C1 C11 O4 66.69(14) . . . . ? C2 C1 C11 O4 -56.06(14) . . . . ? 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 O2 H2A O1 0.847(16) 2.085(17) 2.8674(14) 153(2) 7 O1 H1 O3 0.797(15) 2.311(18) 2.9554(16) 138.4(18) 2_655 O1 H1 O3 0.797(15) 2.165(18) 2.6395(15) 118.4(18) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.227 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.044