# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Shu-Li You' _publ_contact_author_email SLYOU@MAIL.SIOC.AC.CN _publ_section_title ; Intramolecular Phenylogous Michael Addition Reaction for the Synthesis of Benzylbutyrolactones ; loop_ _publ_author_name 'Shu-Li You' 'Li-Xin Dai' 'Hu He' # Attachment 'cd27310.cif' data_cd27310 _database_code_depnum_ccdc_archive 'CCDC 747012' #TrackingRef 'cd27310.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N O5' _chemical_formula_weight 325.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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)/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 5.8692(11) _cell_length_b 7.6984(14) _cell_length_c 34.643(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.634(3) _cell_angle_gamma 90.00 _cell_volume 1560.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2051 _cell_measurement_theta_min 4.704 _cell_measurement_theta_max 44.022 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.496 _exptl_crystal_size_mid 0.267 _exptl_crystal_size_min 0.215 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75534 _exptl_absorpt_correction_T_max 1.00000 _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 8662 _diffrn_reflns_av_R_equivalents 0.1004 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3360 _reflns_number_gt 2039 _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^)+(0.0844P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3360 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1601 _refine_ls_wR_factor_gt 0.1486 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.003 _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 -0.1406(3) 0.4655(2) 0.28212(5) 0.0719(5) Uani 1 1 d . . . O2 O -0.2782(3) 0.69776(19) 0.25100(4) 0.0603(5) Uani 1 1 d . . . O3 O 0.2560(3) 0.7169(3) 0.32055(5) 0.0693(5) Uani 1 1 d . . . O4 O 0.2597(4) 1.1699(4) 0.48766(8) 0.1085(10) Uani 1 1 d . . . O5 O 0.5104(4) 1.2779(3) 0.45270(7) 0.1129(9) Uani 1 1 d . . . N1 N 0.3281(4) 1.2096(3) 0.45639(9) 0.0840(8) Uani 1 1 d . . . C1 C -0.1834(4) 0.6168(3) 0.28230(6) 0.0487(5) Uani 1 1 d . . . C2 C -0.3261(4) 0.8757(3) 0.26033(6) 0.0571(6) Uani 1 1 d . . . H2A H -0.4846 0.8889 0.2658 0.068 Uiso 1 1 calc R . . H2B H -0.2965 0.9516 0.2390 0.068 Uiso 1 1 calc R . . C3 C -0.1670(4) 0.9191(3) 0.29602(6) 0.0476(6) Uani 1 1 d . . . H3 H -0.0175 0.9527 0.2877 0.057 Uiso 1 1 calc R . . C4 C -0.1454(3) 0.7424(3) 0.31556(6) 0.0423(5) Uani 1 1 d . . . H4A H -0.2674 0.7287 0.3330 0.051 Uiso 1 1 calc R . . C5 C 0.0846(3) 0.7106(3) 0.33780(6) 0.0430(5) Uani 1 1 d . . . C6 C 0.0964(3) 0.6796(2) 0.37992(6) 0.0402(5) Uani 1 1 d . . . C7 C -0.0811(4) 0.6100(3) 0.39853(6) 0.0515(6) Uani 1 1 d . . . H7 H -0.2148 0.5761 0.3843 0.062 Uiso 1 1 calc R . . C8 C -0.0614(5) 0.5902(4) 0.43859(7) 0.0718(8) Uani 1 1 d . . . H8 H -0.1800 0.5408 0.4511 0.086 Uiso 1 1 calc R . . C9 C 0.1342(5) 0.6442(4) 0.45955(7) 0.0753(8) Uani 1 1 d . . . H9 H 0.1452 0.6351 0.4864 0.090 Uiso 1 1 calc R . . C10 C 0.3106(5) 0.7101(4) 0.44168(7) 0.0712(8) Uani 1 1 d . . . H10 H 0.4426 0.7449 0.4563 0.085 Uiso 1 1 calc R . . C11 C 0.2966(4) 0.7264(3) 0.40199(6) 0.0528(6) Uani 1 1 d . . . H11 H 0.4209 0.7687 0.3898 0.063 Uiso 1 1 calc R . . C12 C -0.2572(4) 1.0659(3) 0.31973(7) 0.0602(7) Uani 1 1 d . . . H12A H -0.2741 1.1691 0.3037 0.072 Uiso 1 1 calc R . . H12B H -0.4075 1.0345 0.3272 0.072 Uiso 1 1 calc R . . C13 C -0.1051(4) 1.1075(3) 0.35556(7) 0.0513(6) Uani 1 1 d . . . C14 C -0.1687(4) 1.0641(3) 0.39197(8) 0.0594(6) Uani 1 1 d . . . H14 H -0.3094 1.0111 0.3942 0.071 Uiso 1 1 calc R . . C15 C -0.0279(4) 1.0979(3) 0.42509(8) 0.0644(7) Uani 1 1 d . . . H15 H -0.0717 1.0676 0.4494 0.077 Uiso 1 1 calc R . . C16 C 0.1758(4) 1.1763(3) 0.42117(7) 0.0580(6) Uani 1 1 d . . . C17 C 0.2442(4) 1.2235(3) 0.38581(8) 0.0621(7) Uani 1 1 d . . . H17 H 0.3841 1.2783 0.3840 0.074 Uiso 1 1 calc R . . C18 C 0.1030(4) 1.1886(3) 0.35301(7) 0.0584(6) Uani 1 1 d . . . H18 H 0.1484 1.2201 0.3289 0.070 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 0.0864(12) 0.0541(11) 0.0719(12) -0.0109(8) -0.0148(9) 0.0078(9) O2 0.0716(10) 0.0630(10) 0.0430(9) -0.0046(7) -0.0153(8) -0.0019(8) O3 0.0460(9) 0.1144(15) 0.0480(10) 0.0100(9) 0.0069(8) 0.0080(9) O4 0.1033(19) 0.153(3) 0.0618(15) -0.0356(17) -0.0140(14) 0.0013(18) O5 0.0663(14) 0.155(2) 0.1156(19) -0.0536(16) -0.0217(13) 0.0004(14) N1 0.0657(15) 0.1021(19) 0.0810(19) -0.0406(15) -0.0143(14) 0.0193(14) C1 0.0506(12) 0.0502(14) 0.0434(13) -0.0013(10) -0.0071(10) -0.0017(10) C2 0.0639(14) 0.0581(14) 0.0462(13) 0.0054(10) -0.0137(11) 0.0011(11) C3 0.0467(11) 0.0490(13) 0.0447(12) 0.0022(9) -0.0102(10) -0.0012(9) C4 0.0399(10) 0.0499(12) 0.0361(11) 0.0005(8) -0.0030(8) 0.0007(9) C5 0.0371(11) 0.0514(13) 0.0400(12) -0.0010(9) 0.0004(9) 0.0026(9) C6 0.0418(10) 0.0404(11) 0.0371(11) 0.0001(8) -0.0038(8) 0.0069(9) C7 0.0480(12) 0.0534(13) 0.0523(14) 0.0087(10) -0.0001(10) 0.0011(10) C8 0.0777(18) 0.0882(19) 0.0507(16) 0.0242(13) 0.0127(14) 0.0106(14) C9 0.090(2) 0.094(2) 0.0413(15) 0.0129(13) 0.0018(15) 0.0228(17) C10 0.0744(17) 0.0864(19) 0.0480(16) -0.0049(13) -0.0242(14) 0.0131(15) C11 0.0461(12) 0.0597(14) 0.0506(14) -0.0003(10) -0.0074(10) 0.0022(10) C12 0.0604(14) 0.0495(14) 0.0668(16) -0.0033(11) -0.0180(12) 0.0074(11) C13 0.0517(13) 0.0397(12) 0.0603(15) -0.0113(10) -0.0094(11) 0.0081(10) C14 0.0516(13) 0.0551(14) 0.0708(18) -0.0116(12) 0.0002(12) 0.0029(11) C15 0.0662(16) 0.0662(16) 0.0600(16) -0.0135(12) 0.0007(13) 0.0127(13) C16 0.0534(14) 0.0577(14) 0.0609(17) -0.0224(12) -0.0067(12) 0.0125(11) C17 0.0504(13) 0.0536(14) 0.080(2) -0.0119(12) -0.0090(13) -0.0010(11) C18 0.0594(14) 0.0518(14) 0.0628(16) -0.0020(11) -0.0022(11) 0.0028(11) _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 1.192(2) . ? O2 C1 1.333(2) . ? O2 C2 1.440(3) . ? O3 C5 1.211(2) . ? O4 N1 1.224(4) . ? O5 N1 1.208(3) . ? N1 C16 1.476(3) . ? C1 C4 1.507(3) . ? C2 C3 1.525(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C12 1.517(3) . ? C3 C4 1.520(3) . ? C3 H3 0.9800 . ? C4 C5 1.519(3) . ? C4 H4A 0.9800 . ? C5 C6 1.475(3) . ? C6 C7 1.377(3) . ? C6 C11 1.396(3) . ? C7 C8 1.391(3) . ? C7 H7 0.9300 . ? C8 C9 1.372(4) . ? C8 H8 0.9300 . ? C9 C10 1.348(4) . ? C9 H9 0.9300 . ? C10 C11 1.376(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.504(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.381(3) . ? C13 C14 1.385(3) . ? C14 C15 1.383(3) . ? C14 H14 0.9300 . ? C15 C16 1.356(4) . ? C15 H15 0.9300 . ? C16 C17 1.369(4) . ? C17 C18 1.378(3) . ? C17 H17 0.9300 . ? C18 H18 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 O2 C2 109.78(16) . . ? O5 N1 O4 124.0(3) . . ? O5 N1 C16 118.1(3) . . ? O4 N1 C16 117.9(3) . . ? O1 C1 O2 121.81(19) . . ? O1 C1 C4 127.80(19) . . ? O2 C1 C4 110.39(18) . . ? O2 C2 C3 105.81(16) . . ? O2 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? O2 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C12 C3 C4 116.45(19) . . ? C12 C3 C2 112.61(17) . . ? C4 C3 C2 100.87(16) . . ? C12 C3 H3 108.8 . . ? C4 C3 H3 108.8 . . ? C2 C3 H3 108.8 . . ? C1 C4 C5 110.76(17) . . ? C1 C4 C3 103.39(16) . . ? C5 C4 C3 114.12(17) . . ? C1 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? O3 C5 C6 121.33(17) . . ? O3 C5 C4 118.87(19) . . ? C6 C5 C4 119.76(18) . . ? C7 C6 C11 118.62(19) . . ? C7 C6 C5 123.33(18) . . ? C11 C6 C5 118.04(19) . . ? C6 C7 C8 120.3(2) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 119.5(2) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 120.2(2) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C13 C12 C3 113.29(17) . . ? C13 C12 H12A 108.9 . . ? C3 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C3 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C18 C13 C14 118.2(2) . . ? C18 C13 C12 120.9(2) . . ? C14 C13 C12 121.0(2) . . ? C15 C14 C13 121.5(2) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 C15 C14 118.2(3) . . ? C16 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? C15 C16 C17 122.2(2) . . ? C15 C16 N1 118.3(3) . . ? C17 C16 N1 119.5(3) . . ? C16 C17 C18 119.1(2) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C17 C18 C13 120.8(2) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? 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 C2 O2 C1 O1 175.7(2) . . . . ? C2 O2 C1 C4 -3.7(2) . . . . ? C1 O2 C2 C3 22.3(2) . . . . ? O2 C2 C3 C12 -155.45(19) . . . . ? O2 C2 C3 C4 -30.6(2) . . . . ? O1 C1 C4 C5 41.7(3) . . . . ? O2 C1 C4 C5 -138.84(18) . . . . ? O1 C1 C4 C3 164.4(2) . . . . ? O2 C1 C4 C3 -16.2(2) . . . . ? C12 C3 C4 C1 149.72(18) . . . . ? C2 C3 C4 C1 27.5(2) . . . . ? C12 C3 C4 C5 -89.9(2) . . . . ? C2 C3 C4 C5 147.92(19) . . . . ? C1 C4 C5 O3 57.1(3) . . . . ? C3 C4 C5 O3 -59.1(3) . . . . ? C1 C4 C5 C6 -125.3(2) . . . . ? C3 C4 C5 C6 118.5(2) . . . . ? O3 C5 C6 C7 -155.7(2) . . . . ? C4 C5 C6 C7 26.8(3) . . . . ? O3 C5 C6 C11 25.5(3) . . . . ? C4 C5 C6 C11 -152.03(19) . . . . ? C11 C6 C7 C8 1.2(3) . . . . ? C5 C6 C7 C8 -177.6(2) . . . . ? C6 C7 C8 C9 1.5(4) . . . . ? C7 C8 C9 C10 -2.5(4) . . . . ? C8 C9 C10 C11 0.7(4) . . . . ? C9 C10 C11 C6 2.0(4) . . . . ? C7 C6 C11 C10 -2.9(3) . . . . ? C5 C6 C11 C10 175.9(2) . . . . ? C4 C3 C12 C13 62.8(3) . . . . ? C2 C3 C12 C13 178.6(2) . . . . ? C3 C12 C13 C18 71.5(3) . . . . ? C3 C12 C13 C14 -107.9(2) . . . . ? C18 C13 C14 C15 -1.0(3) . . . . ? C12 C13 C14 C15 178.4(2) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C14 C15 C16 C17 0.5(4) . . . . ? C14 C15 C16 N1 -178.9(2) . . . . ? O5 N1 C16 C15 179.3(2) . . . . ? O4 N1 C16 C15 -2.4(4) . . . . ? O5 N1 C16 C17 -0.1(4) . . . . ? O4 N1 C16 C17 178.2(3) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? N1 C16 C17 C18 178.6(2) . . . . ? C16 C17 C18 C13 0.1(3) . . . . ? C14 C13 C18 C17 0.7(3) . . . . ? C12 C13 C18 C17 -178.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.249 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.056 # Attachment 'cd28519.cif' data_cd28519 _database_code_depnum_ccdc_archive 'CCDC 747013' #TrackingRef 'cd28519.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O5' _chemical_formula_weight 289.28 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' N N 0.0061 0.0033 '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)/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 6.8274(9) _cell_length_b 8.8266(11) _cell_length_c 23.345(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.661(2) _cell_angle_gamma 90.00 _cell_volume 1397.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2057 _cell_measurement_theta_min 4.938 _cell_measurement_theta_max 47.521 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.304 _exptl_crystal_size_mid 0.168 _exptl_crystal_size_min 0.155 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7612 _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 7130 _diffrn_reflns_av_R_equivalents 0.0997 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.48 _reflns_number_total 2597 _reflns_number_gt 2003 _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^)+(0.0652P)^2^+0.2079P] 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 2597 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.1538 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 N1 N 0.2540(3) 0.5493(4) -0.06198(12) 0.0842(8) Uani 1 1 d . . . O1 O 0.3367(4) -0.2699(2) 0.12796(10) 0.1119(9) Uani 1 1 d . . . O2 O 0.6605(3) -0.1371(2) 0.25404(9) 0.0883(7) Uani 1 1 d . . . O3 O 0.6869(3) -0.0332(2) 0.16870(9) 0.0748(6) Uani 1 1 d . . . O4 O 0.2725(3) 0.6793(3) -0.04434(12) 0.1077(9) Uani 1 1 d . . . O5 O 0.2415(5) 0.5160(4) -0.11240(11) 0.1306(10) Uani 1 1 d . . . C1 C 0.2818(4) -0.2092(3) 0.16866(10) 0.0580(6) Uani 1 1 d . . . C2 C 0.1311(4) -0.2650(3) 0.20421(11) 0.0670(7) Uani 1 1 d . . . H2A H 0.1440 -0.3734 0.2104 0.080 Uiso 1 1 calc R . . H2B H -0.0006 -0.2434 0.1858 0.080 Uiso 1 1 calc R . . C3 C 0.1712(4) -0.1803(3) 0.26070(11) 0.0689(7) Uani 1 1 d . . . H3A H 0.0516 -0.1692 0.2790 0.083 Uiso 1 1 calc R . . H3B H 0.2694 -0.2324 0.2869 0.083 Uiso 1 1 calc R . . C4 C 0.2466(4) -0.0278(3) 0.24350(10) 0.0604(7) Uani 1 1 d . . . H4A H 0.3301 0.0174 0.2754 0.073 Uiso 1 1 calc R . . H4B H 0.1375 0.0403 0.2321 0.073 Uiso 1 1 calc R . . C5 C 0.3639(3) -0.0570(2) 0.19307(9) 0.0460(5) Uani 1 1 d . . . C6 C 0.5821(4) -0.0827(2) 0.21024(12) 0.0610(7) Uani 1 1 d . . . C7 C 0.5569(4) 0.0343(3) 0.12228(12) 0.0650(7) Uani 1 1 d . . . H7A H 0.5334 -0.0352 0.0900 0.078 Uiso 1 1 calc R . . H7B H 0.6136 0.1268 0.1090 0.078 Uiso 1 1 calc R . . C8 C 0.3668(3) 0.0676(2) 0.14755(9) 0.0463(5) Uani 1 1 d . . . H8 H 0.3825 0.1649 0.1677 0.056 Uiso 1 1 calc R . . C9 C 0.1884(4) 0.0793(3) 0.10293(10) 0.0596(6) Uani 1 1 d . . . H9A H 0.1690 -0.0169 0.0830 0.072 Uiso 1 1 calc R . . H9B H 0.0727 0.0987 0.1223 0.072 Uiso 1 1 calc R . . C10 C 0.2077(3) 0.2026(2) 0.05938(9) 0.0484(5) Uani 1 1 d . . . C11 C 0.2277(3) 0.3525(3) 0.07636(9) 0.0546(6) Uani 1 1 d . . . H11 H 0.2295 0.3769 0.1152 0.066 Uiso 1 1 calc R . . C12 C 0.2450(3) 0.4653(3) 0.03713(10) 0.0578(6) Uani 1 1 d . . . H12 H 0.2591 0.5657 0.0490 0.069 Uiso 1 1 calc R . . C13 C 0.2410(3) 0.4276(3) -0.02005(10) 0.0588(6) Uani 1 1 d . . . C14 C 0.2247(4) 0.2811(3) -0.03833(10) 0.0679(7) Uani 1 1 d . . . H14 H 0.2249 0.2574 -0.0771 0.081 Uiso 1 1 calc R . . C15 C 0.2078(4) 0.1691(3) 0.00162(10) 0.0634(7) Uani 1 1 d . . . H15 H 0.1962 0.0688 -0.0105 0.076 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 N1 0.0647(15) 0.112(2) 0.0762(18) 0.0427(17) 0.0105(12) 0.0147(14) O1 0.178(2) 0.0631(13) 0.1076(17) -0.0409(12) 0.0718(17) -0.0328(14) O2 0.0845(13) 0.0770(13) 0.0990(16) 0.0399(11) -0.0081(11) 0.0047(10) O3 0.0591(10) 0.0691(12) 0.0978(14) 0.0287(10) 0.0156(10) 0.0066(8) O4 0.0965(17) 0.0946(17) 0.132(2) 0.0531(16) 0.0118(14) 0.0014(13) O5 0.160(3) 0.170(3) 0.0624(15) 0.0497(16) 0.0177(15) 0.0156(19) C1 0.0801(17) 0.0383(12) 0.0576(15) -0.0059(10) 0.0161(12) -0.0046(11) C2 0.0699(16) 0.0558(15) 0.0759(18) 0.0058(13) 0.0109(13) -0.0128(12) C3 0.0731(17) 0.0761(18) 0.0605(16) 0.0141(13) 0.0209(13) -0.0017(13) C4 0.0845(17) 0.0533(14) 0.0457(13) -0.0013(10) 0.0170(12) 0.0104(12) C5 0.0605(13) 0.0342(11) 0.0442(12) -0.0018(9) 0.0098(10) 0.0015(9) C6 0.0705(16) 0.0388(12) 0.0737(17) 0.0112(11) 0.0081(13) -0.0002(11) C7 0.0687(16) 0.0615(15) 0.0677(16) 0.0141(12) 0.0198(13) 0.0001(12) C8 0.0583(13) 0.0379(11) 0.0431(12) -0.0010(9) 0.0077(10) -0.0022(9) C9 0.0630(14) 0.0622(15) 0.0527(13) 0.0022(11) 0.0024(11) -0.0114(11) C10 0.0476(12) 0.0564(13) 0.0400(12) -0.0006(10) 0.0001(9) -0.0006(9) C11 0.0645(14) 0.0619(15) 0.0368(12) -0.0020(11) 0.0027(10) 0.0074(11) C12 0.0608(14) 0.0534(14) 0.0578(15) 0.0035(11) 0.0001(11) 0.0055(11) C13 0.0477(13) 0.0776(17) 0.0509(14) 0.0187(13) 0.0046(10) 0.0090(11) C14 0.0800(18) 0.085(2) 0.0384(13) -0.0014(13) 0.0049(12) 0.0114(14) C15 0.0769(17) 0.0644(15) 0.0473(14) -0.0056(12) 0.0003(12) 0.0020(12) _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 N1 O5 1.207(4) . ? N1 O4 1.220(3) . ? N1 C13 1.463(3) . ? O1 C1 1.189(3) . ? O2 C6 1.198(3) . ? O3 C6 1.343(3) . ? O3 C7 1.447(3) . ? C1 C2 1.479(3) . ? C1 C5 1.539(3) . ? C2 C3 1.513(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.512(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.521(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.514(3) . ? C5 C8 1.531(3) . ? C7 C8 1.515(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.511(3) . ? C8 H8 0.9800 . ? C9 C10 1.506(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C15 1.381(3) . ? C10 C11 1.383(3) . ? C11 C12 1.367(3) . ? C11 H11 0.9300 . ? C12 C13 1.373(3) . ? C12 H12 0.9300 . ? C13 C14 1.362(4) . ? C14 C15 1.373(3) . ? C14 H14 0.9300 . ? C15 H15 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 O5 N1 O4 123.4(3) . . ? O5 N1 C13 118.1(3) . . ? O4 N1 C13 118.5(3) . . ? C6 O3 C7 110.05(19) . . ? O1 C1 C2 127.1(2) . . ? O1 C1 C5 123.7(2) . . ? C2 C1 C5 109.3(2) . . ? C1 C2 C3 104.9(2) . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.8 . . ? C4 C3 C2 103.95(19) . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C3 C4 C5 106.31(18) . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4B 110.5 . . ? C5 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C6 C5 C4 114.2(2) . . ? C6 C5 C8 101.52(17) . . ? C4 C5 C8 117.76(17) . . ? C6 C5 C1 105.83(17) . . ? C4 C5 C1 103.46(18) . . ? C8 C5 C1 113.79(18) . . ? O2 C6 O3 121.6(2) . . ? O2 C6 C5 127.9(2) . . ? O3 C6 C5 110.5(2) . . ? O3 C7 C8 105.47(19) . . ? O3 C7 H7A 110.6 . . ? C8 C7 H7A 110.6 . . ? O3 C7 H7B 110.6 . . ? C8 C7 H7B 110.6 . . ? H7A C7 H7B 108.8 . . ? C9 C8 C7 113.8(2) . . ? C9 C8 C5 116.95(18) . . ? C7 C8 C5 102.21(17) . . ? C9 C8 H8 107.8 . . ? C7 C8 H8 107.8 . . ? C5 C8 H8 107.8 . . ? C10 C9 C8 112.84(19) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C15 C10 C11 118.3(2) . . ? C15 C10 C9 121.0(2) . . ? C11 C10 C9 120.8(2) . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 118.7(2) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 121.8(2) . . ? C14 C13 N1 119.8(3) . . ? C12 C13 N1 118.4(3) . . ? C13 C14 C15 118.8(2) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C14 C15 C10 121.2(2) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? 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 159.5(3) . . . . ? C5 C1 C2 C3 -19.4(3) . . . . ? C1 C2 C3 C4 32.8(3) . . . . ? C2 C3 C4 C5 -34.4(3) . . . . ? C3 C4 C5 C6 -92.4(2) . . . . ? C3 C4 C5 C8 148.6(2) . . . . ? C3 C4 C5 C1 22.2(2) . . . . ? O1 C1 C5 C6 -60.1(3) . . . . ? C2 C1 C5 C6 118.9(2) . . . . ? O1 C1 C5 C4 179.4(3) . . . . ? C2 C1 C5 C4 -1.6(3) . . . . ? O1 C1 C5 C8 50.5(3) . . . . ? C2 C1 C5 C8 -130.5(2) . . . . ? C7 O3 C6 O2 -176.9(2) . . . . ? C7 O3 C6 C5 2.5(3) . . . . ? C4 C5 C6 O2 30.2(3) . . . . ? C8 C5 C6 O2 158.1(3) . . . . ? C1 C5 C6 O2 -82.9(3) . . . . ? C4 C5 C6 O3 -149.05(19) . . . . ? C8 C5 C6 O3 -21.2(2) . . . . ? C1 C5 C6 O3 97.8(2) . . . . ? C6 O3 C7 C8 17.9(3) . . . . ? O3 C7 C8 C9 -157.00(19) . . . . ? O3 C7 C8 C5 -30.0(2) . . . . ? C6 C5 C8 C9 155.0(2) . . . . ? C4 C5 C8 C9 -79.5(3) . . . . ? C1 C5 C8 C9 41.8(3) . . . . ? C6 C5 C8 C7 30.1(2) . . . . ? C4 C5 C8 C7 155.6(2) . . . . ? C1 C5 C8 C7 -83.1(2) . . . . ? C7 C8 C9 C10 -59.7(3) . . . . ? C5 C8 C9 C10 -178.64(19) . . . . ? C8 C9 C10 C15 117.7(2) . . . . ? C8 C9 C10 C11 -61.7(3) . . . . ? C15 C10 C11 C12 0.8(3) . . . . ? C9 C10 C11 C12 -179.9(2) . . . . ? C10 C11 C12 C13 0.4(3) . . . . ? C11 C12 C13 C14 -1.4(4) . . . . ? C11 C12 C13 N1 178.3(2) . . . . ? O5 N1 C13 C14 3.0(4) . . . . ? O4 N1 C13 C14 -178.6(3) . . . . ? O5 N1 C13 C12 -176.7(3) . . . . ? O4 N1 C13 C12 1.7(4) . . . . ? C12 C13 C14 C15 1.3(4) . . . . ? N1 C13 C14 C15 -178.4(2) . . . . ? C13 C14 C15 C10 -0.2(4) . . . . ? C11 C10 C15 C14 -0.9(4) . . . . ? C9 C10 C15 C14 179.8(2) . . . . ? 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 C12 H12 O1 0.93 2.36 3.169(3) 145.6 1_565 C8 H8 O2 0.98 2.57 3.494(3) 157.4 2_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.046