# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is (c) the Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Min Shi' _publ_contact_author_email MSHI@MAIL.SIOC.AC.CN _publ_section_title ; The Reaction of Acyl Cyanides with "Huisgen Zwitterion": an Interesting Rearrangement Involving Ester Group "Jumping" between Oxygen Atom and Nitrogen Atom ; loop_ _publ_author_name 'Min Shi.' 'Xu-Guang Liu.' 'Yin Wei.' # Attachment 'cd28573.cif' data_cd28573 _database_code_depnum_ccdc_archive 'CCDC 713523' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Cl N3 O4' _chemical_formula_weight 351.78 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' Cl Cl 0.1484 0.1585 '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 10.8230(18) _cell_length_b 6.4408(11) _cell_length_c 25.686(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.893(3) _cell_angle_gamma 90.00 _cell_volume 1758.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2120 _cell_measurement_theta_min 5.459 _cell_measurement_theta_max 44.378 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.378 _exptl_crystal_size_mid 0.346 _exptl_crystal_size_min 0.267 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7534 _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 9077 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3434 _reflns_number_gt 2333 _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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3434 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.003 _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 Cl1 Cl 0.06546(6) 1.15872(11) 1.10757(3) 0.0848(3) Uani 1 1 d . . . N1 N 0.22308(14) 0.4853(3) 0.93327(6) 0.0467(4) Uani 1 1 d . . . N2 N 0.27192(14) 0.3757(3) 0.89483(6) 0.0444(4) Uani 1 1 d . . . N3 N 0.46169(18) 0.8114(3) 0.91342(8) 0.0675(6) Uani 1 1 d . . . O1 O 0.46732(13) 0.3234(2) 0.94587(6) 0.0533(4) Uani 1 1 d . . . O2 O 0.43782(11) 0.3014(2) 0.85706(5) 0.0497(4) Uani 1 1 d . . . O3 O 0.07201(13) 0.3413(2) 0.84822(6) 0.0588(4) Uani 1 1 d . . . O4 O 0.22084(11) 0.1072(2) 0.83890(5) 0.0485(4) Uani 1 1 d . . . C1 C 0.27858(16) 0.6520(3) 0.95162(7) 0.0402(5) Uani 1 1 d . . . C2 C 0.38418(19) 0.7399(3) 0.93153(8) 0.0463(5) Uani 1 1 d . . . C3 C 0.40369(18) 0.3278(3) 0.90278(8) 0.0418(5) Uani 1 1 d . . . C4 C 0.56918(18) 0.2420(3) 0.85808(9) 0.0543(6) Uani 1 1 d . . . H4 H 0.6028 0.1703 0.8914 0.065 Uiso 1 1 calc R . . C5 C 0.5668(2) 0.0966(5) 0.81248(11) 0.0879(9) Uani 1 1 d . . . H5A H 0.5184 -0.0242 0.8174 0.132 Uiso 1 1 calc R . . H5B H 0.6512 0.0560 0.8107 0.132 Uiso 1 1 calc R . . H5C H 0.5293 0.1649 0.7801 0.132 Uiso 1 1 calc R . . C6 C 0.6425(2) 0.4358(4) 0.85424(12) 0.0830(8) Uani 1 1 d . . . H6A H 0.6073 0.5083 0.8222 0.125 Uiso 1 1 calc R . . H6B H 0.7285 0.4008 0.8538 0.125 Uiso 1 1 calc R . . H6C H 0.6389 0.5230 0.8842 0.125 Uiso 1 1 calc R . . C7 C 0.17740(19) 0.2759(3) 0.85823(8) 0.0437(5) Uani 1 1 d . . . C8 C 0.14372(19) 0.0182(3) 0.79116(8) 0.0509(5) Uani 1 1 d . . . H8 H 0.0551 0.0187 0.7947 0.061 Uiso 1 1 calc R . . C9 C 0.1594(2) 0.1480(4) 0.74453(9) 0.0748(7) Uani 1 1 d . . . H9A H 0.1303 0.2864 0.7490 0.112 Uiso 1 1 calc R . . H9B H 0.1113 0.0888 0.7128 0.112 Uiso 1 1 calc R . . H9C H 0.2467 0.1519 0.7419 0.112 Uiso 1 1 calc R . . C10 C 0.1880(2) -0.2004(4) 0.78871(11) 0.0792(8) Uani 1 1 d . . . H10A H 0.2772 -0.2014 0.7902 0.119 Uiso 1 1 calc R . . H10B H 0.1464 -0.2633 0.7562 0.119 Uiso 1 1 calc R . . H10C H 0.1687 -0.2772 0.8182 0.119 Uiso 1 1 calc R . . C11 C 0.22977(16) 0.7743(3) 0.99155(7) 0.0400(5) Uani 1 1 d . . . C12 C 0.13760(18) 0.6912(3) 1.01672(8) 0.0513(5) Uani 1 1 d . . . H12 H 0.1100 0.5557 1.0094 0.062 Uiso 1 1 calc R . . C13 C 0.08707(19) 0.8080(4) 1.05236(9) 0.0570(6) Uani 1 1 d . . . H13 H 0.0254 0.7525 1.0690 0.068 Uiso 1 1 calc R . . C14 C 0.12867(19) 1.0069(4) 1.06297(8) 0.0532(6) Uani 1 1 d . . . C15 C 0.22041(19) 1.0915(3) 1.03916(8) 0.0537(6) Uani 1 1 d . . . H15 H 0.2478 1.2269 1.0469 0.064 Uiso 1 1 calc R . . C16 C 0.27133(18) 0.9742(3) 1.00383(8) 0.0480(5) Uani 1 1 d . . . H16 H 0.3344 1.0300 0.9880 0.058 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 Cl1 0.0871(5) 0.1008(6) 0.0710(5) -0.0337(4) 0.0265(4) 0.0103(4) N1 0.0477(10) 0.0470(10) 0.0478(10) -0.0099(8) 0.0153(8) -0.0056(8) N2 0.0423(9) 0.0476(10) 0.0447(10) -0.0119(8) 0.0115(7) -0.0056(8) N3 0.0685(13) 0.0599(13) 0.0815(15) -0.0037(10) 0.0328(12) -0.0142(10) O1 0.0544(8) 0.0627(10) 0.0415(9) 0.0009(7) 0.0057(7) 0.0078(7) O2 0.0422(7) 0.0689(10) 0.0398(8) -0.0013(7) 0.0125(6) -0.0018(6) O3 0.0437(8) 0.0686(10) 0.0633(10) -0.0117(8) 0.0080(7) 0.0048(7) O4 0.0474(8) 0.0482(8) 0.0468(8) -0.0100(7) 0.0007(6) 0.0016(6) C1 0.0386(10) 0.0417(12) 0.0407(11) 0.0014(9) 0.0084(8) -0.0022(9) C2 0.0487(12) 0.0419(12) 0.0492(13) -0.0051(9) 0.0122(10) -0.0034(10) C3 0.0485(11) 0.0394(12) 0.0386(12) 0.0009(9) 0.0110(10) -0.0019(9) C4 0.0451(12) 0.0685(15) 0.0521(14) 0.0062(11) 0.0160(10) 0.0059(11) C5 0.0839(18) 0.100(2) 0.092(2) -0.0216(17) 0.0466(16) -0.0014(16) C6 0.0552(14) 0.091(2) 0.106(2) 0.0034(16) 0.0223(14) -0.0142(14) C7 0.0475(12) 0.0430(12) 0.0415(12) -0.0013(9) 0.0107(9) -0.0023(10) C8 0.0478(12) 0.0589(14) 0.0445(12) -0.0128(10) 0.0047(10) -0.0090(10) C9 0.0862(18) 0.0880(19) 0.0497(15) 0.0006(13) 0.0113(13) 0.0028(14) C10 0.0914(19) 0.0578(16) 0.0815(19) -0.0237(13) -0.0015(15) -0.0030(13) C11 0.0378(10) 0.0422(12) 0.0392(11) -0.0018(9) 0.0049(8) 0.0001(9) C12 0.0489(12) 0.0523(13) 0.0545(13) -0.0085(10) 0.0142(10) -0.0096(10) C13 0.0503(12) 0.0726(16) 0.0517(14) -0.0068(11) 0.0191(11) -0.0041(11) C14 0.0484(12) 0.0668(15) 0.0433(13) -0.0113(11) 0.0061(10) 0.0113(11) C15 0.0574(13) 0.0476(13) 0.0547(14) -0.0095(10) 0.0072(11) -0.0005(10) C16 0.0501(12) 0.0463(13) 0.0477(12) -0.0018(10) 0.0097(10) -0.0037(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 Cl1 C14 1.741(2) . ? N1 C1 1.276(2) . ? N1 N2 1.396(2) . ? N2 C7 1.407(2) . ? N2 C3 1.436(2) . ? N3 C2 1.131(2) . ? O1 C3 1.188(2) . ? O2 C3 1.307(2) . ? O2 C4 1.468(2) . ? O3 C7 1.197(2) . ? O4 C7 1.318(2) . ? O4 C8 1.463(2) . ? C1 C2 1.455(3) . ? C1 C11 1.468(2) . ? C4 C6 1.493(3) . ? C4 C5 1.496(3) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C8 C10 1.493(3) . ? C8 C9 1.496(3) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.381(3) . ? C11 C12 1.394(3) . ? C12 C13 1.376(3) . ? C12 H12 0.9300 . ? C13 C14 1.368(3) . ? C13 H13 0.9300 . ? C14 C15 1.373(3) . ? C15 C16 1.374(3) . ? C15 H15 0.9300 . ? C16 H16 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 N1 N2 118.15(15) . . ? N1 N2 C7 112.27(14) . . ? N1 N2 C3 120.46(15) . . ? C7 N2 C3 125.02(16) . . ? C3 O2 C4 117.08(16) . . ? C7 O4 C8 116.81(15) . . ? N1 C1 C2 122.88(17) . . ? N1 C1 C11 120.18(16) . . ? C2 C1 C11 116.72(16) . . ? N3 C2 C1 176.2(2) . . ? O1 C3 O2 128.42(19) . . ? O1 C3 N2 121.52(18) . . ? O2 C3 N2 110.01(17) . . ? O2 C4 C6 107.82(17) . . ? O2 C4 C5 106.03(18) . . ? C6 C4 C5 113.7(2) . . ? O2 C4 H4 109.7 . . ? C6 C4 H4 109.7 . . ? C5 C4 H4 109.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O3 C7 O4 127.04(18) . . ? O3 C7 N2 121.69(18) . . ? O4 C7 N2 111.25(17) . . ? O4 C8 C10 105.55(18) . . ? O4 C8 C9 108.60(18) . . ? C10 C8 C9 114.0(2) . . ? O4 C8 H8 109.5 . . ? C10 C8 H8 109.5 . . ? C9 C8 H8 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 118.86(18) . . ? C16 C11 C1 121.01(17) . . ? C12 C11 C1 120.10(17) . . ? C13 C12 C11 120.53(19) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 119.18(19) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 121.41(19) . . ? C13 C14 Cl1 120.10(17) . . ? C15 C14 Cl1 118.49(18) . . ? C14 C15 C16 119.3(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C15 C16 C11 120.67(18) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? 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 C1 N1 N2 C7 -147.01(18) . . . . ? C1 N1 N2 C3 49.2(3) . . . . ? N2 N1 C1 C2 4.6(3) . . . . ? N2 N1 C1 C11 179.14(16) . . . . ? N1 C1 C2 N3 72(3) . . . . ? C11 C1 C2 N3 -102(3) . . . . ? C4 O2 C3 O1 5.5(3) . . . . ? C4 O2 C3 N2 -177.35(15) . . . . ? N1 N2 C3 O1 22.0(3) . . . . ? C7 N2 C3 O1 -139.6(2) . . . . ? N1 N2 C3 O2 -155.42(16) . . . . ? C7 N2 C3 O2 43.0(2) . . . . ? C3 O2 C4 C6 -93.7(2) . . . . ? C3 O2 C4 C5 144.11(19) . . . . ? C8 O4 C7 O3 16.5(3) . . . . ? C8 O4 C7 N2 -164.79(15) . . . . ? N1 N2 C7 O3 27.6(3) . . . . ? C3 N2 C7 O3 -169.49(18) . . . . ? N1 N2 C7 O4 -151.18(16) . . . . ? C3 N2 C7 O4 11.7(3) . . . . ? C7 O4 C8 C10 -161.01(18) . . . . ? C7 O4 C8 C9 76.3(2) . . . . ? N1 C1 C11 C16 -166.44(18) . . . . ? C2 C1 C11 C16 8.4(3) . . . . ? N1 C1 C11 C12 11.8(3) . . . . ? C2 C1 C11 C12 -173.34(18) . . . . ? C16 C11 C12 C13 1.3(3) . . . . ? C1 C11 C12 C13 -176.95(19) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 -0.6(3) . . . . ? C12 C13 C14 Cl1 179.55(17) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? Cl1 C14 C15 C16 -179.95(16) . . . . ? C14 C15 C16 C11 1.0(3) . . . . ? C12 C11 C16 C15 -1.8(3) . . . . ? C1 C11 C16 C15 176.52(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.247 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.038 # Attachment 'cd29130.cif' data_cd29130 _database_code_depnum_ccdc_archive 'CCDC 724590' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H25 N3 O7' _chemical_formula_weight 407.42 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5749(13) _cell_length_b 12.355(2) _cell_length_c 12.896(2) _cell_angle_alpha 99.071(3) _cell_angle_beta 102.604(3) _cell_angle_gamma 106.451(3) _cell_volume 1098.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1163 _cell_measurement_theta_min 5.396 _cell_measurement_theta_max 46.283 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.423 _exptl_crystal_size_min 0.351 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7488 _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 6074 _diffrn_reflns_av_R_equivalents 0.1019 _diffrn_reflns_av_sigmaI/netI 0.0998 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4247 _reflns_number_gt 1967 _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^)+(0.0593P)^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 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4247 _refine_ls_number_parameters 291 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1196 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1559 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.854 _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 O1 O 0.0125(3) 0.42701(16) 0.17637(14) 0.0715(6) Uani 1 1 d . . . O2 O -0.2989(2) 0.49136(17) 0.12165(14) 0.0744(6) Uani 1 1 d . . . O3 O -0.3744(3) 0.63977(17) 0.25994(15) 0.0777(6) Uani 1 1 d . . . O4 O 0.0900(3) 0.86202(18) 0.78617(16) 0.0804(6) Uani 1 1 d . . . O5 O 0.2172(3) 0.99461(18) 0.6997(2) 0.0957(7) Uani 1 1 d . . . O6 O -0.0775(3) 0.9607(2) 0.7222(2) 0.1110(8) Uani 1 1 d . B . O7 O 0.3436(3) 0.85538(17) 0.90050(15) 0.0842(6) Uani 1 1 d . . . N1 N 0.1529(3) 0.73401(19) 0.62147(18) 0.0646(6) Uani 1 1 d . . . N2 N 0.2875(3) 0.76224(19) 0.72288(17) 0.0661(6) Uani 1 1 d . . . N3 N 0.4993(4) 0.6139(3) 0.5893(2) 0.1186(12) Uani 1 1 d . . . C1 C 0.1074(3) 0.5474(2) 0.36104(19) 0.0567(7) Uani 1 1 d . . . H1 H 0.2146 0.5250 0.3821 0.068 Uiso 1 1 calc R . . C2 C -0.0122(4) 0.5045(2) 0.2553(2) 0.0570(7) Uani 1 1 d . . . C3 C -0.1734(4) 0.5370(2) 0.2243(2) 0.0591(7) Uani 1 1 d . . . C4 C -0.2142(3) 0.6136(2) 0.2997(2) 0.0583(7) Uani 1 1 d . . . C5 C -0.0961(3) 0.6562(2) 0.4053(2) 0.0589(7) Uani 1 1 d . . . H5 H -0.1249 0.7061 0.4560 0.071 Uiso 1 1 calc R . . C6 C 0.0657(3) 0.6242(2) 0.43529(19) 0.0533(6) Uani 1 1 d . . . C7 C 0.1922(3) 0.6689(2) 0.5483(2) 0.0548(7) Uani 1 1 d . . . C8 C 0.3633(5) 0.6381(3) 0.5738(2) 0.0721(8) Uani 1 1 d . . . C9 C 0.1745(4) 0.3901(2) 0.2045(2) 0.0757(8) Uani 1 1 d . . . H9A H 0.2895 0.4551 0.2200 0.114 Uiso 1 1 calc R . . H9B H 0.1704 0.3316 0.1446 0.114 Uiso 1 1 calc R . . H9C H 0.1728 0.3586 0.2679 0.114 Uiso 1 1 calc R . . C10 C -0.2379(4) 0.5406(3) 0.0378(2) 0.0917(10) Uani 1 1 d . . . H10A H -0.2236 0.6217 0.0531 0.138 Uiso 1 1 calc R . . H10B H -0.3315 0.5019 -0.0312 0.138 Uiso 1 1 calc R . . H10C H -0.1173 0.5314 0.0350 0.138 Uiso 1 1 calc R . . C11 C -0.4244(4) 0.7181(3) 0.3321(3) 0.0886(10) Uani 1 1 d . . . H11A H -0.4310 0.6910 0.3973 0.133 Uiso 1 1 calc R . . H11B H -0.5467 0.7226 0.2969 0.133 Uiso 1 1 calc R . . H11C H -0.3291 0.7937 0.3506 0.133 Uiso 1 1 calc R . . C12 C 0.2484(4) 0.8251(3) 0.7973(3) 0.0713(8) Uani 1 1 d . . . C13 C 0.0895(5) 0.9460(3) 0.7315(3) 0.0734(8) Uani 1 1 d . . . C14 C -0.1151(6) 1.0518(4) 0.6726(5) 0.1199(14) Uani 1 1 d D . . H14 H 0.0146 1.1065 0.6871 0.144 Uiso 1 1 calc R A 1 C15 C -0.169(4) 1.0119(14) 0.5555(10) 0.129(8) Uani 0.335(18) 1 d PD B 1 H15A H -0.2856 0.9472 0.5322 0.194 Uiso 0.335(18) 1 calc PR B 1 H15B H -0.0690 0.9884 0.5341 0.194 Uiso 0.335(18) 1 calc PR B 1 H15C H -0.1871 1.0736 0.5223 0.194 Uiso 0.335(18) 1 calc PR B 1 C16 C -0.209(5) 1.125(3) 0.725(3) 0.23(2) Uani 0.335(18) 1 d P B 1 H16A H -0.2169 1.1851 0.6864 0.329 Uiso 0.335(18) 1 calc PR B 1 H16B H -0.1357 1.1600 0.7994 0.329 Uiso 0.335(18) 1 calc PR B 1 H16C H -0.3356 1.0786 0.7223 0.329 Uiso 0.335(18) 1 calc PR B 1 C15' C -0.314(2) 0.9982(10) 0.5938(13) 0.218(7) Uani 0.665(18) 1 d PD B 2 H15D H -0.3116 0.9424 0.5336 0.327 Uiso 0.665(18) 1 calc PR B 2 H15E H -0.3549 1.0578 0.5670 0.327 Uiso 0.665(18) 1 calc PR B 2 H15F H -0.4015 0.9602 0.6309 0.327 Uiso 0.665(18) 1 calc PR B 2 C16' C -0.121(2) 1.1341(8) 0.7643(13) 0.160(5) Uani 0.665(18) 1 d P B 2 H16D H -0.2049 1.0940 0.8022 0.240 Uiso 0.665(18) 1 calc PR B 2 H16E H -0.1676 1.1922 0.7381 0.240 Uiso 0.665(18) 1 calc PR B 2 H16F H 0.0055 1.1704 0.8133 0.240 Uiso 0.665(18) 1 calc PR B 2 C17 C 0.4924(5) 0.8049(3) 0.9368(2) 0.0845(10) Uani 1 1 d . . . H17 H 0.4594 0.7271 0.8905 0.101 Uiso 1 1 calc R . . C18 C 0.6785(6) 0.8799(3) 0.9303(3) 0.1195(13) Uani 1 1 d . . . H18A H 0.6709 0.8835 0.8557 0.179 Uiso 1 1 calc R . . H18B H 0.7769 0.8484 0.9570 0.179 Uiso 1 1 calc R . . H18C H 0.7083 0.9566 0.9741 0.179 Uiso 1 1 calc R . . C19 C 0.4868(6) 0.7963(3) 1.0513(3) 0.1281(14) Uani 1 1 d . . . H19A H 0.5100 0.8720 1.0950 0.192 Uiso 1 1 calc R . . H19B H 0.5836 0.7655 1.0824 0.192 Uiso 1 1 calc R . . H19C H 0.3631 0.7458 1.0494 0.192 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 0.0794(13) 0.0812(13) 0.0484(11) 0.0038(10) 0.0074(9) 0.0318(11) O2 0.0700(12) 0.0904(14) 0.0439(10) 0.0111(10) -0.0021(9) 0.0137(10) O3 0.0693(12) 0.0950(15) 0.0668(13) 0.0177(11) 0.0069(10) 0.0340(11) O4 0.0929(15) 0.0813(14) 0.0760(14) 0.0275(12) 0.0292(11) 0.0331(12) O5 0.0839(15) 0.0887(16) 0.1194(19) 0.0330(14) 0.0421(14) 0.0207(12) O6 0.1041(18) 0.130(2) 0.138(2) 0.0609(18) 0.0564(15) 0.0642(16) O7 0.1195(16) 0.0774(14) 0.0489(12) -0.0033(10) 0.0075(11) 0.0441(12) N1 0.0686(14) 0.0659(15) 0.0491(13) 0.0058(12) 0.0068(11) 0.0181(12) N2 0.0815(15) 0.0656(15) 0.0424(13) 0.0028(11) 0.0058(12) 0.0250(12) N3 0.109(2) 0.177(3) 0.0639(18) -0.0069(18) -0.0078(16) 0.082(2) C1 0.0574(15) 0.0625(17) 0.0462(15) 0.0167(14) 0.0084(13) 0.0159(13) C2 0.0678(17) 0.0560(17) 0.0400(14) 0.0104(13) 0.0103(13) 0.0135(14) C3 0.0592(16) 0.0645(18) 0.0437(15) 0.0157(14) 0.0055(13) 0.0103(14) C4 0.0533(16) 0.0666(18) 0.0528(16) 0.0195(14) 0.0079(13) 0.0186(14) C5 0.0591(16) 0.0649(18) 0.0513(16) 0.0144(14) 0.0148(13) 0.0183(13) C6 0.0556(15) 0.0525(16) 0.0424(14) 0.0124(13) 0.0079(12) 0.0074(13) C7 0.0626(17) 0.0514(16) 0.0456(15) 0.0144(13) 0.0095(13) 0.0139(13) C8 0.078(2) 0.091(2) 0.0373(15) 0.0018(14) 0.0013(14) 0.0300(18) C9 0.089(2) 0.079(2) 0.0611(17) 0.0109(16) 0.0195(16) 0.0345(17) C10 0.097(2) 0.125(3) 0.0500(17) 0.0304(19) 0.0087(16) 0.037(2) C11 0.072(2) 0.106(3) 0.095(2) 0.024(2) 0.0256(18) 0.0391(18) C12 0.084(2) 0.0633(19) 0.061(2) 0.0092(16) 0.0098(16) 0.0278(17) C13 0.075(2) 0.071(2) 0.069(2) 0.0060(17) 0.0194(17) 0.0238(18) C14 0.106(3) 0.130(4) 0.160(5) 0.066(4) 0.043(3) 0.071(3) C15 0.164(17) 0.163(13) 0.088(10) 0.049(9) 0.026(9) 0.090(12) C16 0.30(3) 0.38(5) 0.23(3) 0.18(3) 0.17(3) 0.31(4) C15' 0.222(14) 0.270(12) 0.158(10) 0.008(9) -0.018(10) 0.149(11) C16' 0.225(12) 0.078(6) 0.197(11) 0.044(6) 0.058(10) 0.072(6) C17 0.127(3) 0.071(2) 0.0498(17) 0.0015(15) -0.0013(18) 0.050(2) C18 0.128(3) 0.112(3) 0.116(3) 0.000(3) 0.025(3) 0.057(3) C19 0.202(4) 0.127(3) 0.060(2) 0.018(2) 0.021(2) 0.075(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 C2 1.365(3) . ? O1 C9 1.421(3) . ? O2 C3 1.373(3) . ? O2 C10 1.420(3) . ? O3 C4 1.357(3) . ? O3 C11 1.422(3) . ? O4 C13 1.344(4) . ? O4 C12 1.387(3) . ? O5 C13 1.177(3) . ? O6 C13 1.311(3) . ? O6 C14 1.445(4) . ? O7 C12 1.305(3) . ? O7 C17 1.463(3) . ? N1 C7 1.282(3) . ? N1 N2 1.395(3) . ? N2 C12 1.277(3) . ? N3 C8 1.137(3) . ? C1 C2 1.386(3) . ? C1 C6 1.390(3) . ? C1 H1 0.9300 . ? C2 C3 1.389(3) . ? C3 C4 1.393(4) . ? C4 C5 1.382(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 C7 1.478(3) . ? C7 C8 1.438(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C14 C15 1.439(12) . ? C14 C16' 1.450(13) . ? C14 C16 1.47(3) . ? C14 C15' 1.515(11) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C15' H15D 0.9600 . ? C15' H15E 0.9600 . ? C15' H15F 0.9600 . ? C16' H16D 0.9600 . ? C16' H16E 0.9600 . ? C16' H16F 0.9600 . ? C17 C18 1.479(4) . ? C17 C19 1.506(4) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 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 C2 O1 C9 117.4(2) . . ? C3 O2 C10 115.1(2) . . ? C4 O3 C11 117.7(2) . . ? C13 O4 C12 116.2(2) . . ? C13 O6 C14 118.9(3) . . ? C12 O7 C17 118.5(2) . . ? C7 N1 N2 111.8(2) . . ? C12 N2 N1 112.7(2) . . ? C2 C1 C6 119.4(2) . . ? C2 C1 H1 120.3 . . ? C6 C1 H1 120.3 . . ? O1 C2 C1 124.5(2) . . ? O1 C2 C3 115.3(2) . . ? C1 C2 C3 120.2(3) . . ? O2 C3 C2 121.2(3) . . ? O2 C3 C4 118.9(2) . . ? C2 C3 C4 119.8(2) . . ? O3 C4 C5 125.2(3) . . ? O3 C4 C3 114.6(2) . . ? C5 C4 C3 120.2(2) . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 120.7(2) . . ? C5 C6 C7 119.9(2) . . ? C1 C6 C7 119.4(2) . . ? N1 C7 C8 120.7(2) . . ? N1 C7 C6 121.6(2) . . ? C8 C7 C6 117.8(2) . . ? N3 C8 C7 176.8(3) . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 H11A 109.5 . . ? O3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 O7 124.5(3) . . ? N2 C12 O4 127.0(3) . . ? O7 C12 O4 108.2(3) . . ? O5 C13 O6 128.7(3) . . ? O5 C13 O4 125.0(3) . . ? O6 C13 O4 106.3(3) . . ? C15 C14 O6 109.2(7) . . ? C15 C14 C16' 146.2(8) . . ? O6 C14 C16' 102.6(6) . . ? C15 C14 C16 120.6(13) . . ? O6 C14 C16 118.3(12) . . ? C16' C14 C16 28.3(14) . . ? C15 C14 C15' 51.4(7) . . ? O6 C14 C15' 105.9(6) . . ? C16' C14 C15' 109.1(7) . . ? C16 C14 C15' 81.8(13) . . ? C15 C14 H14 101.6 . . ? O6 C14 H14 101.6 . . ? C16' C14 H14 82.7 . . ? C16 C14 H14 101.6 . . ? C15' C14 H14 146.6 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? C14 C15' H15D 109.5 . . ? C14 C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C14 C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? C14 C16' H16D 109.5 . . ? C14 C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? C14 C16' H16F 109.5 . . ? H16D C16' H16F 109.5 . . ? H16E C16' H16F 109.5 . . ? O7 C17 C18 109.6(3) . . ? O7 C17 C19 103.9(3) . . ? C18 C17 C19 113.8(3) . . ? O7 C17 H17 109.8 . . ? C18 C17 H17 109.8 . . ? C19 C17 H17 109.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C7 N1 N2 C12 -178.6(2) . . . . ? C9 O1 C2 C1 -1.4(4) . . . . ? C9 O1 C2 C3 -179.3(2) . . . . ? C6 C1 C2 O1 -178.6(2) . . . . ? C6 C1 C2 C3 -0.8(4) . . . . ? C10 O2 C3 C2 -78.5(3) . . . . ? C10 O2 C3 C4 104.2(3) . . . . ? O1 C2 C3 O2 1.2(3) . . . . ? C1 C2 C3 O2 -176.8(2) . . . . ? O1 C2 C3 C4 178.5(2) . . . . ? C1 C2 C3 C4 0.4(4) . . . . ? C11 O3 C4 C5 0.7(4) . . . . ? C11 O3 C4 C3 -179.6(2) . . . . ? O2 C3 C4 O3 -3.2(3) . . . . ? C2 C3 C4 O3 179.5(2) . . . . ? O2 C3 C4 C5 176.6(2) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? O3 C4 C5 C6 -178.9(2) . . . . ? C3 C4 C5 C6 1.4(4) . . . . ? C4 C5 C6 C1 -1.7(4) . . . . ? C4 C5 C6 C7 -179.6(2) . . . . ? C2 C1 C6 C5 1.4(4) . . . . ? C2 C1 C6 C7 179.3(2) . . . . ? N2 N1 C7 C8 -3.0(4) . . . . ? N2 N1 C7 C6 177.7(2) . . . . ? C5 C6 C7 N1 2.4(4) . . . . ? C1 C6 C7 N1 -175.5(2) . . . . ? C5 C6 C7 C8 -176.8(2) . . . . ? C1 C6 C7 C8 5.2(3) . . . . ? N1 C7 C8 N3 -145(6) . . . . ? C6 C7 C8 N3 35(6) . . . . ? N1 N2 C12 O7 174.4(2) . . . . ? N1 N2 C12 O4 1.9(4) . . . . ? C17 O7 C12 N2 -6.8(5) . . . . ? C17 O7 C12 O4 166.9(2) . . . . ? C13 O4 C12 N2 -73.4(4) . . . . ? C13 O4 C12 O7 113.1(3) . . . . ? C14 O6 C13 O5 -3.9(5) . . . . ? C14 O6 C13 O4 176.0(3) . . . . ? C12 O4 C13 O5 -5.4(4) . . . . ? C12 O4 C13 O6 174.7(2) . . . . ? C13 O6 C14 C15 81.0(12) . . . . ? C13 O6 C14 C16' -110.8(7) . . . . ? C13 O6 C14 C16 -135.9(18) . . . . ? C13 O6 C14 C15' 134.9(9) . . . . ? C12 O7 C17 C18 90.7(3) . . . . ? C12 O7 C17 C19 -147.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.250 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.037