# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Pauline Chiu' 'Sze Kar Leung' _publ_contact_author_name 'Dr Pauline Chiu' _publ_contact_author_address ; Department of Chemistry The University of Hong Kong Pokfulam Road Hong Kong CHINA ; _publ_contact_author_email PCHIU@HKU.HK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Stoichiometric and Catalytic Reductive Aldol Cyclizations of Alkynediones Induced by Stryker's Reagent ; data_mar302 _database_code_depnum_ccdc_archive 'CCDC 240836' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 N4 O7' _chemical_formula_sum 'C22 H26 N4 O7' _chemical_formula_weight 458.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 7.4600(15) _cell_length_b 8.6090(17) _cell_length_c 18.302(4) _cell_angle_alpha 77.02(3) _cell_angle_beta 85.05(3) _cell_angle_gamma 89.89(3) _cell_volume 1140.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.101 _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 301(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'marresearach IPDS mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5057 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3078 _reflns_number_gt 2179 _reflns_threshold_expression >2sigma(I) _computing_data_collection Marcontrol _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1350P)^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 3078 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1912 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.8055(2) 0.0745(2) 0.78985(12) 0.0569(6) Uani 1 1 d . . . O2 O 0.7075(3) -0.1895(3) 0.70663(15) 0.0826(7) Uani 1 1 d . . . O3 O 0.9879(3) -0.0876(2) 0.68060(14) 0.0801(7) Uani 1 1 d . . . O4 O 0.1391(3) 0.1166(4) 1.04543(15) 0.0874(8) Uani 1 1 d . . . O5 O 0.1243(3) 0.2749(3) 1.12170(15) 0.0897(8) Uani 1 1 d . . . O6 O 0.6600(4) 0.4871(3) 1.19128(16) 0.1003(9) Uani 1 1 d . . . O7 O 0.8764(4) 0.5533(3) 1.10442(17) 0.0949(8) Uani 1 1 d . . . N1 N 0.2086(4) 0.2122(4) 1.07632(16) 0.0679(8) Uani 1 1 d . . . N2 N 0.7368(5) 0.4800(3) 1.13084(19) 0.0737(8) Uani 1 1 d . . . N3 N 0.4115(4) 0.1565(3) 0.94289(15) 0.0596(7) Uani 1 1 d . . . N4 N 0.4984(3) 0.1519(3) 0.87425(13) 0.0527(6) Uani 1 1 d . . . C1 C 0.6959(3) 0.1574(3) 0.73338(15) 0.0443(7) Uani 1 1 d . . . C2 C 0.7439(4) 0.0953(3) 0.65996(16) 0.0511(7) Uani 1 1 d . . . C3 C 0.8861(4) 0.1981(3) 0.60366(17) 0.0587(8) Uani 1 1 d . . . H3A H 0.9875 0.2148 0.6310 0.070 Uiso 1 1 calc R . . H3B H 0.9288 0.1373 0.5672 0.070 Uiso 1 1 calc R . . C4 C 0.8292(4) 0.3578(4) 0.56135(17) 0.0607(8) Uani 1 1 d . . . H4 H 0.8755 0.3859 0.5112 0.073 Uiso 1 1 calc R . . C5 C 0.7235(4) 0.4658(4) 0.58368(17) 0.0587(8) Uani 1 1 d . . . C6 C 0.6369(4) 0.4478(3) 0.66222(17) 0.0591(8) Uani 1 1 d . . . H6A H 0.5142 0.4095 0.6635 0.071 Uiso 1 1 calc R . . H6B H 0.6311 0.5525 0.6737 0.071 Uiso 1 1 calc R . . C7 C 0.7294(4) 0.3361(3) 0.72432(16) 0.0524(7) Uani 1 1 d . . . H7A H 0.6911 0.3635 0.7718 0.063 Uiso 1 1 calc R . . H7B H 0.8580 0.3567 0.7149 0.063 Uiso 1 1 calc R . . C8 C 0.4976(3) 0.1125(3) 0.75239(16) 0.0466(7) Uani 1 1 d . . . C9 C 0.4269(4) 0.0804(4) 0.69330(18) 0.0602(8) Uani 1 1 d . . . H9 H 0.3055 0.0562 0.6931 0.072 Uiso 1 1 calc R . . C10 C 0.5599(4) 0.0867(4) 0.62729(18) 0.0627(8) Uani 1 1 d . . . H10A H 0.5429 0.1801 0.5877 0.075 Uiso 1 1 calc R . . H10B H 0.5503 -0.0080 0.6073 0.075 Uiso 1 1 calc R . . C11 C 0.6799(5) 0.6174(4) 0.5304(2) 0.0805(10) Uani 1 1 d . . . H11A H 0.6023 0.6799 0.5566 0.121 Uiso 1 1 calc R . . H11B H 0.6204 0.5929 0.4898 0.121 Uiso 1 1 calc R . . H11C H 0.7890 0.6766 0.5106 0.121 Uiso 1 1 calc R . . C12 C 0.4023(3) 0.1138(3) 0.82508(17) 0.0502(7) Uani 1 1 d . . . C13 C 0.8067(5) -0.0766(4) 0.68505(18) 0.0622(9) Uani 1 1 d . . . C14 C 1.0612(6) -0.2441(5) 0.7040(3) 0.1058(15) Uani 1 1 d . . . H14A H 1.1445 -0.2424 0.7417 0.127 Uiso 1 1 calc R . . H14B H 0.9645 -0.3193 0.7268 0.127 Uiso 1 1 calc R . . C15 C 1.1504(9) -0.2945(6) 0.6435(3) 0.144(2) Uani 1 1 d . . . H15A H 1.1974 -0.3989 0.6610 0.215 Uiso 1 1 calc R . . H15B H 1.2475 -0.2214 0.6215 0.215 Uiso 1 1 calc R . . H15C H 1.0677 -0.2980 0.6065 0.215 Uiso 1 1 calc R . . C16 C 0.2062(4) 0.0730(4) 0.8399(2) 0.0735(10) Uani 1 1 d . . . H16A H 0.1658 0.0796 0.8903 0.110 Uiso 1 1 calc R . . H16B H 0.1860 -0.0334 0.8340 0.110 Uiso 1 1 calc R . . H16C H 0.1405 0.1466 0.8049 0.110 Uiso 1 1 calc R . . C17 C 0.4913(4) 0.2254(3) 0.99105(16) 0.0511(8) Uani 1 1 d . . . C18 C 0.3987(4) 0.2539(4) 1.05749(17) 0.0563(8) Uani 1 1 d . . . C19 C 0.4795(5) 0.3321(4) 1.10458(18) 0.0639(9) Uani 1 1 d . . . H19 H 0.4170 0.3481 1.1484 0.077 Uiso 1 1 calc R . . C20 C 0.6540(5) 0.3857(4) 1.08521(18) 0.0606(8) Uani 1 1 d . . . C21 C 0.7519(4) 0.3598(4) 1.02115(18) 0.0610(8) Uani 1 1 d . . . H21 H 0.8704 0.3965 1.0093 0.073 Uiso 1 1 calc R . . C22 C 0.6718(4) 0.2796(4) 0.97547(17) 0.0581(8) Uani 1 1 d . . . H22 H 0.7383 0.2605 0.9331 0.070 Uiso 1 1 calc R . . H1 H 0.763(8) 0.111(7) 0.840(3) 0.18(2) Uiso 1 1 d . . . H2 H 0.301(5) 0.131(4) 0.9600(19) 0.081(11) 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 O1 0.0426(11) 0.0645(13) 0.0611(13) -0.0057(10) -0.0129(9) 0.0055(9) O2 0.0836(16) 0.0480(14) 0.115(2) -0.0168(13) -0.0054(14) -0.0125(12) O3 0.0671(16) 0.0546(14) 0.1096(19) -0.0056(12) 0.0079(13) 0.0154(11) O4 0.0642(15) 0.111(2) 0.0805(18) -0.0163(16) 0.0146(13) -0.0191(15) O5 0.0700(15) 0.1022(19) 0.0867(17) -0.0107(15) 0.0207(13) 0.0191(14) O6 0.125(2) 0.104(2) 0.0760(18) -0.0319(16) -0.0002(17) 0.0079(17) O7 0.0865(18) 0.0864(19) 0.119(2) -0.0416(16) -0.0014(17) -0.0060(16) N1 0.0592(18) 0.0727(19) 0.0578(18) 0.0085(15) 0.0116(14) 0.0112(15) N2 0.080(2) 0.0604(18) 0.081(2) -0.0153(16) -0.0087(18) 0.0164(17) N3 0.0466(15) 0.0706(17) 0.0537(17) -0.0003(13) 0.0033(14) 0.0022(13) N4 0.0434(13) 0.0571(15) 0.0514(15) -0.0010(12) 0.0002(12) 0.0035(11) C1 0.0375(15) 0.0445(15) 0.0496(17) -0.0063(12) -0.0083(12) 0.0005(12) C2 0.0484(16) 0.0466(16) 0.0587(18) -0.0113(13) -0.0085(13) -0.0012(13) C3 0.0589(18) 0.0525(18) 0.0637(19) -0.0151(15) 0.0049(15) 0.0008(14) C4 0.066(2) 0.0590(19) 0.0521(18) -0.0042(15) 0.0014(15) -0.0073(16) C5 0.0578(18) 0.0510(18) 0.064(2) -0.0038(15) -0.0092(15) -0.0053(15) C6 0.0622(19) 0.0400(16) 0.073(2) -0.0106(14) -0.0030(16) -0.0001(14) C7 0.0482(16) 0.0535(17) 0.0561(18) -0.0154(14) -0.0002(13) -0.0098(13) C8 0.0388(14) 0.0428(15) 0.0575(18) -0.0080(13) -0.0096(13) -0.0037(12) C9 0.0448(15) 0.0551(18) 0.080(2) -0.0108(16) -0.0121(16) -0.0083(14) C10 0.0638(19) 0.062(2) 0.066(2) -0.0182(15) -0.0144(16) -0.0113(16) C11 0.092(3) 0.063(2) 0.079(2) 0.0023(18) -0.015(2) 0.0029(19) C12 0.0399(15) 0.0430(16) 0.063(2) -0.0021(13) -0.0065(14) -0.0023(13) C13 0.068(2) 0.0500(19) 0.069(2) -0.0172(16) -0.0020(16) -0.0027(17) C14 0.095(3) 0.070(3) 0.138(4) -0.002(2) 0.013(3) 0.037(2) C15 0.212(6) 0.117(4) 0.107(4) -0.042(3) 0.002(4) 0.078(4) C16 0.0467(17) 0.087(2) 0.087(2) -0.023(2) 0.0026(16) -0.0124(17) C17 0.0464(17) 0.0490(17) 0.0509(18) 0.0031(14) -0.0033(14) 0.0079(14) C18 0.0516(17) 0.0518(18) 0.0552(19) 0.0068(15) 0.0025(15) 0.0053(14) C19 0.069(2) 0.0533(18) 0.059(2) 0.0042(16) 0.0072(17) 0.0161(17) C20 0.071(2) 0.0494(18) 0.061(2) -0.0093(15) -0.0102(17) 0.0139(16) C21 0.0547(18) 0.0536(18) 0.070(2) -0.0053(16) -0.0030(16) 0.0058(15) C22 0.0521(18) 0.0599(19) 0.0566(19) -0.0030(16) -0.0002(14) 0.0060(15) _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 1.435(3) . ? O2 C13 1.195(4) . ? O3 C13 1.352(4) . ? O3 C14 1.441(4) . ? O4 N1 1.236(4) . ? O5 N1 1.219(3) . ? O6 N2 1.215(4) . ? O7 N2 1.223(4) . ? N1 C18 1.456(4) . ? N2 C20 1.461(4) . ? N3 C17 1.345(4) . ? N3 N4 1.372(3) . ? N4 C12 1.295(4) . ? C1 C8 1.521(4) . ? C1 C7 1.528(4) . ? C1 C2 1.568(4) . ? C2 C13 1.533(4) . ? C2 C3 1.541(4) . ? C2 C10 1.553(4) . ? C3 C4 1.499(4) . ? C4 C5 1.329(4) . ? C5 C11 1.498(4) . ? C5 C6 1.499(4) . ? C6 C7 1.528(4) . ? C8 C9 1.326(4) . ? C8 C12 1.455(4) . ? C9 C10 1.487(4) . ? C12 C16 1.493(4) . ? C14 C15 1.395(5) . ? C17 C22 1.410(4) . ? C17 C18 1.416(4) . ? C18 C19 1.383(5) . ? C19 C20 1.372(5) . ? C20 C21 1.388(4) . ? C21 C22 1.371(4) . ? 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 C13 O3 C14 117.2(3) . . ? O5 N1 O4 122.8(3) . . ? O5 N1 C18 118.2(3) . . ? O4 N1 C18 119.0(3) . . ? O6 N2 O7 123.5(3) . . ? O6 N2 C20 118.6(3) . . ? O7 N2 C20 117.8(3) . . ? C17 N3 N4 120.4(3) . . ? C12 N4 N3 117.0(2) . . ? O1 C1 C8 112.2(2) . . ? O1 C1 C7 107.8(2) . . ? C8 C1 C7 111.8(2) . . ? O1 C1 C2 107.8(2) . . ? C8 C1 C2 102.9(2) . . ? C7 C1 C2 114.3(2) . . ? C13 C2 C3 111.2(2) . . ? C13 C2 C10 106.9(2) . . ? C3 C2 C10 113.2(2) . . ? C13 C2 C1 106.7(2) . . ? C3 C2 C1 114.2(2) . . ? C10 C2 C1 104.0(2) . . ? C4 C3 C2 117.4(2) . . ? C5 C4 C3 130.6(3) . . ? C4 C5 C11 121.5(3) . . ? C4 C5 C6 124.1(3) . . ? C11 C5 C6 114.4(3) . . ? C5 C6 C7 116.2(2) . . ? C6 C7 C1 116.8(2) . . ? C9 C8 C12 126.4(3) . . ? C9 C8 C1 110.5(2) . . ? C12 C8 C1 123.0(2) . . ? C8 C9 C10 113.7(3) . . ? C9 C10 C2 103.5(2) . . ? N4 C12 C8 115.7(2) . . ? N4 C12 C16 123.6(3) . . ? C8 C12 C16 120.7(3) . . ? O2 C13 O3 123.1(3) . . ? O2 C13 C2 124.2(3) . . ? O3 C13 C2 112.7(3) . . ? C15 C14 O3 111.5(3) . . ? N3 C17 C22 120.8(3) . . ? N3 C17 C18 122.6(3) . . ? C22 C17 C18 116.5(3) . . ? C19 C18 C17 122.1(3) . . ? C19 C18 N1 116.8(3) . . ? C17 C18 N1 121.0(3) . . ? C20 C19 C18 118.5(3) . . ? C19 C20 C21 121.9(3) . . ? C19 C20 N2 119.3(3) . . ? C21 C20 N2 118.7(3) . . ? C22 C21 C20 119.2(3) . . ? C21 C22 C17 121.7(3) . . ? _diffrn_measured_fraction_theta_max 0.725 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.725 _refine_diff_density_max 0.399 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.091 data_mar269a _database_code_depnum_ccdc_archive 'CCDC 240837' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 O4' _chemical_formula_sum 'C14 H20 O4' _chemical_formula_weight 252.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 7.3680(15) _cell_length_b 9.1860(18) _cell_length_c 10.640(2) _cell_angle_alpha 77.73(3) _cell_angle_beta 76.61(3) _cell_angle_gamma 89.91(3) _cell_volume 683.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9654 _exptl_absorpt_correction_T_max 0.9825 _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 'marresearch IPDS mar300' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3246 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.53 _reflns_number_total 1933 _reflns_number_gt 1500 _reflns_threshold_expression >2sigma(I) _computing_data_collection Marcontrol _computing_cell_refinement Scalepack _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1240P)^2^+0.0838P] 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 1933 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1917 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 0.1753(3) -0.2014(2) 0.4766(2) 0.0739(6) Uani 1 1 d . . . O2 O 0.2158(2) 0.1636(2) 0.42598(16) 0.0578(5) Uani 1 1 d . . . H2 H 0.1450 0.2317 0.4151 0.087 Uiso 1 1 calc R . . O3 O 0.4584(4) 0.4799(3) 0.2001(3) 0.1095(10) Uani 1 1 d . . . O4 O 0.1780(3) 0.4036(2) 0.1922(3) 0.0983(8) Uani 1 1 d . . . C1 C 0.3977(3) -0.0190(3) 0.3372(2) 0.0455(6) Uani 1 1 d . . . C2 C 0.2670(3) 0.1061(2) 0.3077(2) 0.0427(6) Uani 1 1 d . . . C3 C 0.4037(3) 0.2227(3) 0.1979(2) 0.0510(6) Uani 1 1 d . . . C4 C 0.5944(3) 0.1935(3) 0.2326(3) 0.0650(8) Uani 1 1 d . . . H4A H 0.6954 0.2117 0.1535 0.078 Uiso 1 1 calc R . . H4B H 0.6171 0.2554 0.2913 0.078 Uiso 1 1 calc R . . C5 C 0.5739(3) 0.0345(3) 0.2991(3) 0.0600(7) Uani 1 1 d . . . H5 H 0.6744 -0.0229 0.3132 0.072 Uiso 1 1 calc R . . C6 C 0.3365(3) -0.1711(3) 0.4149(2) 0.0521(6) Uani 1 1 d . . . C7 C 0.4760(4) -0.2893(3) 0.4162(3) 0.0699(8) Uani 1 1 d . . . H7A H 0.4164 -0.3817 0.4704 0.105 Uiso 1 1 calc R . . H7B H 0.5757 -0.2605 0.4514 0.105 Uiso 1 1 calc R . . H7C H 0.5254 -0.3016 0.3275 0.105 Uiso 1 1 calc R . . C8 C 0.0914(3) 0.0625(3) 0.2685(2) 0.0493(6) Uani 1 1 d . . . H8A H 0.0257 -0.0214 0.3351 0.059 Uiso 1 1 calc R . . H8B H 0.0095 0.1453 0.2663 0.059 Uiso 1 1 calc R . . C9 C 0.1346(4) 0.0207(3) 0.1347(3) 0.0633(8) Uani 1 1 d . . . H9A H 0.2118 -0.0650 0.1372 0.076 Uiso 1 1 calc R . . H9B H 0.0192 -0.0062 0.1141 0.076 Uiso 1 1 calc R . . C10 C 0.2354(4) 0.1500(4) 0.0286(3) 0.0703(8) Uani 1 1 d . . . H10A H 0.1570 0.2350 0.0246 0.084 Uiso 1 1 calc R . . H10B H 0.2608 0.1228 -0.0568 0.084 Uiso 1 1 calc R . . C11 C 0.4185(4) 0.1920(3) 0.0586(2) 0.0604(7) Uani 1 1 d . . . H11A H 0.4747 0.2804 -0.0066 0.072 Uiso 1 1 calc R . . H11B H 0.5027 0.1120 0.0476 0.072 Uiso 1 1 calc R . . C12 C 0.3535(4) 0.3809(3) 0.1990(3) 0.0708(8) Uani 1 1 d . . . C13 C 0.1111(7) 0.5531(4) 0.1959(7) 0.154(2) Uani 1 1 d . . . H13A H 0.1981 0.6070 0.2275 0.185 Uiso 1 1 calc R . . H13B H 0.1126 0.6052 0.1062 0.185 Uiso 1 1 calc R . . C14 C -0.0508(8) 0.5571(6) 0.2676(8) 0.206(4) Uani 1 1 d . . . H14A H -0.0819 0.6591 0.2650 0.309 Uiso 1 1 calc R . . H14B H -0.0540 0.5073 0.3571 0.309 Uiso 1 1 calc R . . H14C H -0.1395 0.5081 0.2351 0.309 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 0.0527(11) 0.0673(13) 0.0817(15) 0.0040(10) 0.0053(10) 0.0065(9) O2 0.0518(10) 0.0733(12) 0.0534(11) -0.0274(8) -0.0103(8) 0.0102(8) O3 0.1086(19) 0.0614(14) 0.154(3) -0.0312(14) -0.0142(16) -0.0215(13) O4 0.0808(16) 0.0522(13) 0.146(2) -0.0093(12) -0.0074(14) 0.0162(11) C1 0.0354(11) 0.0590(15) 0.0442(13) -0.0156(10) -0.0096(10) 0.0050(10) C2 0.0360(11) 0.0509(14) 0.0413(13) -0.0123(10) -0.0072(10) 0.0021(9) C3 0.0450(13) 0.0518(15) 0.0519(15) -0.0111(10) -0.0028(11) -0.0031(10) C4 0.0430(13) 0.079(2) 0.0688(18) -0.0173(14) -0.0047(12) -0.0122(12) C5 0.0371(13) 0.0781(19) 0.0640(17) -0.0144(13) -0.0116(11) 0.0043(12) C6 0.0458(13) 0.0634(16) 0.0489(15) -0.0150(11) -0.0121(12) 0.0116(11) C7 0.0639(17) 0.0642(18) 0.083(2) -0.0176(14) -0.0186(15) 0.0182(13) C8 0.0366(12) 0.0597(15) 0.0509(14) -0.0076(11) -0.0129(10) 0.0011(10) C9 0.0580(15) 0.0832(19) 0.0548(17) -0.0189(13) -0.0221(13) -0.0058(13) C10 0.0751(18) 0.090(2) 0.0466(16) -0.0132(13) -0.0182(14) 0.0060(15) C11 0.0612(16) 0.0622(17) 0.0475(16) -0.0049(11) 0.0009(12) -0.0027(12) C12 0.0664(18) 0.0588(18) 0.076(2) -0.0105(13) 0.0027(15) -0.0011(15) C13 0.119(4) 0.058(2) 0.242(6) -0.011(3) 0.025(4) 0.030(2) C14 0.132(4) 0.084(3) 0.317(9) 0.002(4) 0.076(5) 0.034(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 C6 1.217(3) . ? O2 C2 1.438(3) . ? O3 C12 1.198(4) . ? O4 C12 1.326(4) . ? O4 C13 1.463(4) . ? C1 C5 1.328(3) . ? C1 C6 1.475(4) . ? C1 C2 1.527(3) . ? C2 C8 1.526(3) . ? C2 C3 1.566(3) . ? C3 C12 1.501(4) . ? C3 C4 1.543(4) . ? C3 C11 1.546(4) . ? C4 C5 1.473(4) . ? C6 C7 1.494(4) . ? C8 C9 1.516(3) . ? C9 C10 1.511(4) . ? C10 C11 1.524(4) . ? C13 C14 1.264(6) . ? 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 C12 O4 C13 117.5(3) . . ? C5 C1 C6 124.6(2) . . ? C5 C1 C2 110.0(2) . . ? C6 C1 C2 124.82(19) . . ? O2 C2 C8 109.82(16) . . ? O2 C2 C1 105.65(17) . . ? C8 C2 C1 116.14(18) . . ? O2 C2 C3 109.01(17) . . ? C8 C2 C3 114.48(18) . . ? C1 C2 C3 101.04(17) . . ? C12 C3 C4 110.6(2) . . ? C12 C3 C11 110.1(2) . . ? C4 C3 C11 107.8(2) . . ? C12 C3 C2 112.9(2) . . ? C4 C3 C2 103.27(19) . . ? C11 C3 C2 111.74(18) . . ? C5 C4 C3 102.74(19) . . ? C1 C5 C4 113.4(2) . . ? O1 C6 C1 121.2(2) . . ? O1 C6 C7 119.9(2) . . ? C1 C6 C7 118.9(2) . . ? C9 C8 C2 112.56(18) . . ? C10 C9 C8 110.2(2) . . ? C9 C10 C11 110.2(2) . . ? C10 C11 C3 115.9(2) . . ? O3 C12 O4 122.0(3) . . ? O3 C12 C3 125.5(3) . . ? O4 C12 C3 112.4(3) . . ? C14 C13 O4 115.3(4) . . ? _diffrn_measured_fraction_theta_max 0.763 _diffrn_reflns_theta_full 25.53 _diffrn_measured_fraction_theta_full 0.763 _refine_diff_density_max 0.266 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.079