# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'Kummer, David' 'Li, Derun' 'Dion, Amelie' 'Myers, A.' _publ_contact_author_name 'Myers, A.' _publ_contact_author_email myers@chemistry.harvard.edu _publ_section_title ; A Practical, Convergent Route to the Key Precursor to the Tetracycline Antibiotics ; # Attachment '- HCl salt of compound 26.cif' data_AD-2-5 _database_code_depnum_ccdc_archive 'CCDC 826311' #TrackingRef '- HCl salt of compound 26.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C33.25 H37.25 Cl1.50 N2 O4 Si' _chemical_formula_weight 610.17 _chemical_absolute_configuration ad _chemical_melting_point ? 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' Cl Cl 0.1484 0.1585 '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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z' 3 'x+1/2, -y+1/2, -z' 4 '-x+1/2, y+1/2, -z' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P21212 _cell_length_a 8.3338(7) _cell_length_b 25.680(2) _cell_length_c 15.2004(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3253.0(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2276 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 20.9 _cell_measurement_theta_min 2.56 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_T_max 0.9770 _exptl_absorpt_correction_T_min 0.9289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1289 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 18394 _diffrn_reflns_theta_full 26.13 _diffrn_reflns_theta_max 26.13 _diffrn_reflns_theta_min 1.56 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _reflns_number_gt 4579 _reflns_number_total 6403 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.215 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.077 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.08(10) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 388 _refine_ls_number_reflns 6403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0605 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1480 _refine_ls_wR_factor_ref 0.1668 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.67902(13) 0.26001(4) 0.40084(7) 0.0352(3) Uani 1 1 d . . . Si1 Si 0.35299(15) 0.14745(5) 0.87917(9) 0.0345(3) Uani 1 1 d . . . O1 O 0.8406(4) 0.11150(10) 0.31784(18) 0.0291(7) Uani 1 1 d . . . O2 O 0.7884(3) -0.02169(10) 0.32803(18) 0.0286(7) Uani 1 1 d . . . O3 O 0.8175(4) -0.01274(10) 0.53190(18) 0.0308(7) Uani 1 1 d . . . O4 O 0.8083(3) 0.01049(10) 0.69220(18) 0.0291(7) Uani 1 1 d . . . H4O H 0.7903 -0.0090 0.6489 0.035 Uiso 1 1 calc R . . N1 N 0.8220(4) 0.06252(13) 0.2762(2) 0.0294(8) Uani 1 1 d . . . N2 N 1.0297(4) 0.16541(12) 0.4719(2) 0.0229(7) Uani 1 1 d . . . H2N H 1.0671 0.1868 0.5124 0.028 Uiso 1 1 d R . . C1 C 0.8090(5) 0.02945(15) 0.3412(3) 0.0272(9) Uani 1 1 d . . . C2 C 0.8179(5) 0.05374(15) 0.4244(3) 0.0255(9) Uani 1 1 d . . . C3 C 0.8153(5) 0.03522(15) 0.5151(3) 0.0244(9) Uani 1 1 d . . . C4 C 0.8065(5) 0.07441(14) 0.5816(3) 0.0227(9) Uani 1 1 d . . . C5 C 0.7957(5) 0.05998(15) 0.6675(3) 0.0254(9) Uani 1 1 d . . . C6 C 0.7585(5) 0.09520(16) 0.7419(3) 0.0263(9) Uani 1 1 d . . . H6A H 0.8345 0.0881 0.7914 0.032 Uiso 1 1 calc R . . C7 C 0.5809(5) 0.08650(16) 0.7747(3) 0.0288(10) Uani 1 1 d . . . H7A H 0.5619 0.0543 0.8103 0.035 Uiso 1 1 calc R . . C8 C 0.4773(5) 0.09271(18) 0.6938(3) 0.0328(11) Uani 1 1 d . . . H8A H 0.4217 0.0658 0.6637 0.039 Uiso 1 1 calc R . . C9 C 0.4785(5) 0.14202(18) 0.6732(3) 0.0315(10) Uani 1 1 d . . . H9A H 0.4226 0.1575 0.6254 0.038 Uiso 1 1 calc R . . C10 C 0.5836(5) 0.17011(16) 0.7381(3) 0.0260(9) Uani 1 1 d . . . H10A H 0.5639 0.2084 0.7437 0.031 Uiso 1 1 calc R . . C11 C 0.7614(5) 0.15394(15) 0.7201(3) 0.0244(9) Uani 1 1 d . . . H11A H 0.8293 0.1713 0.7656 0.029 Uiso 1 1 calc R . . C12 C 0.8327(5) 0.16722(14) 0.6309(3) 0.0244(8) Uani 1 1 d . . . H12A H 0.9511 0.1668 0.6360 0.029 Uiso 1 1 calc R . . H12B H 0.8003 0.2031 0.6152 0.029 Uiso 1 1 calc R . . C13 C 0.7831(5) 0.13059(15) 0.5561(2) 0.0232(9) Uani 1 1 d . . . H13A H 0.6646 0.1353 0.5492 0.028 Uiso 1 1 calc R . . C14 C 0.8569(5) 0.14802(15) 0.4679(3) 0.0243(9) Uani 1 1 d . . . H14A H 0.7917 0.1778 0.4452 0.029 Uiso 1 1 calc R . . C15 C 0.8376(5) 0.10368(14) 0.4056(3) 0.0234(8) Uani 1 1 d . . . C16 C 0.7702(6) -0.03710(17) 0.2363(3) 0.0337(10) Uani 1 1 d . . . H16A H 0.8708 -0.0302 0.2036 0.040 Uiso 1 1 calc R . . H16B H 0.6827 -0.0169 0.2084 0.040 Uiso 1 1 calc R . . C17 C 0.7317(5) -0.09391(16) 0.2340(3) 0.0272(9) Uani 1 1 d . . . C18 C 0.8263(6) -0.12774(16) 0.1863(3) 0.0304(9) Uani 1 1 d . . . H18A H 0.9205 -0.1154 0.1579 0.037 Uiso 1 1 calc R . . C19 C 0.7835(6) -0.17948(18) 0.1799(3) 0.0350(11) Uani 1 1 d . . . H19A H 0.8471 -0.2027 0.1460 0.042 Uiso 1 1 calc R . . C20 C 0.6492(6) -0.19739(17) 0.2226(3) 0.0359(11) Uani 1 1 d . . . H20A H 0.6203 -0.2331 0.2176 0.043 Uiso 1 1 calc R . . C21 C 0.5562(6) -0.16475(18) 0.2721(3) 0.0370(11) Uani 1 1 d . . . H21A H 0.4644 -0.1777 0.3020 0.044 Uiso 1 1 calc R . . C22 C 0.5975(5) -0.11258(18) 0.2780(3) 0.0356(11) Uani 1 1 d . . . H22A H 0.5339 -0.0895 0.3123 0.043 Uiso 1 1 calc R . . C23 C 0.5502(5) 0.13772(16) 0.8212(3) 0.0283(10) Uani 1 1 d . . . H23A H 0.6389 0.1439 0.8643 0.034 Uiso 1 1 calc R . . C24 C 0.1733(6) 0.1312(2) 0.8124(4) 0.0541(15) Uani 1 1 d . . . H24A H 0.0771 0.1335 0.8493 0.081 Uiso 1 1 calc R . . H24B H 0.1836 0.0957 0.7895 0.081 Uiso 1 1 calc R . . H24C H 0.1643 0.1557 0.7633 0.081 Uiso 1 1 calc R . . C25 C 0.3573(8) 0.10587(19) 0.9774(3) 0.0592(16) Uani 1 1 d . . . H25A H 0.2574 0.1104 1.0106 0.089 Uiso 1 1 calc R . . H25B H 0.4486 0.1157 1.0145 0.089 Uiso 1 1 calc R . . H25C H 0.3680 0.0694 0.9596 0.089 Uiso 1 1 calc R . . C26 C 0.3450(5) 0.21760(16) 0.9107(3) 0.0294(10) Uani 1 1 d . . . C27 C 0.4084(5) 0.23470(17) 0.9903(3) 0.0323(10) Uani 1 1 d . . . H27A H 0.4534 0.2101 1.0299 0.039 Uiso 1 1 calc R . . C28 C 0.4070(6) 0.28679(19) 1.0129(3) 0.0401(12) Uani 1 1 d . . . H28A H 0.4520 0.2975 1.0674 0.048 Uiso 1 1 calc R . . C29 C 0.3413(6) 0.32330(18) 0.9574(3) 0.0418(12) Uani 1 1 d . . . H29A H 0.3387 0.3590 0.9740 0.050 Uiso 1 1 calc R . . C30 C 0.2790(5) 0.30769(18) 0.8773(3) 0.0391(11) Uani 1 1 d . . . H30A H 0.2348 0.3327 0.8381 0.047 Uiso 1 1 calc R . . C31 C 0.2812(5) 0.25552(19) 0.8543(3) 0.0358(11) Uani 1 1 d . . . H31A H 0.2385 0.2452 0.7991 0.043 Uiso 1 1 calc R . . C32 C 1.1461(5) 0.12305(15) 0.4910(3) 0.0321(10) Uani 1 1 d . . . H32A H 1.2536 0.1379 0.4981 0.048 Uiso 1 1 calc R . . H32B H 1.1466 0.0981 0.4421 0.048 Uiso 1 1 calc R . . H32C H 1.1147 0.1052 0.5453 0.048 Uiso 1 1 calc R . . C33 C 1.0760(5) 0.19440(17) 0.3914(3) 0.0327(10) Uani 1 1 d . . . H33A H 1.1827 0.2097 0.3995 0.049 Uiso 1 1 calc R . . H33B H 0.9978 0.2221 0.3803 0.049 Uiso 1 1 calc R . . H33C H 1.0780 0.1705 0.3411 0.049 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 0.0371(6) 0.0284(5) 0.0402(6) -0.0049(5) -0.0063(5) 0.0115(5) Si1 0.0326(6) 0.0313(7) 0.0394(7) -0.0076(6) 0.0116(6) -0.0052(5) O1 0.0357(16) 0.0210(15) 0.0306(16) -0.0027(12) -0.0010(14) 0.0008(13) O2 0.0356(16) 0.0189(15) 0.0313(15) -0.0039(12) -0.0029(13) 0.0009(12) O3 0.0389(17) 0.0197(15) 0.0339(16) -0.0007(12) 0.0030(14) -0.0009(13) O4 0.0340(17) 0.0184(15) 0.0351(16) -0.0020(12) 0.0040(14) 0.0010(12) N1 0.033(2) 0.0225(18) 0.033(2) -0.0025(16) -0.0005(17) -0.0014(16) N2 0.0263(17) 0.0178(18) 0.0247(18) 0.0014(15) -0.0018(15) -0.0014(14) C1 0.020(2) 0.025(2) 0.037(2) 0.0010(19) 0.0013(18) -0.0003(17) C2 0.025(2) 0.019(2) 0.032(2) -0.0011(17) 0.0042(19) 0.0000(17) C3 0.022(2) 0.020(2) 0.031(2) 0.0054(18) 0.0001(18) -0.0020(17) C4 0.025(2) 0.0138(19) 0.029(2) -0.0019(16) 0.0056(18) 0.0004(16) C5 0.020(2) 0.017(2) 0.040(3) 0.0000(18) 0.0026(18) -0.0008(16) C6 0.024(2) 0.028(2) 0.027(2) 0.0007(19) 0.0009(18) 0.0015(17) C7 0.031(2) 0.019(2) 0.036(3) -0.0032(19) 0.0100(19) -0.0031(18) C8 0.022(2) 0.035(3) 0.042(3) -0.017(2) 0.006(2) -0.0039(18) C9 0.020(2) 0.043(3) 0.032(2) -0.005(2) 0.0002(18) 0.0042(18) C10 0.025(2) 0.023(2) 0.030(2) -0.0049(19) 0.0005(18) 0.0018(16) C11 0.024(2) 0.019(2) 0.030(2) -0.0030(18) -0.0021(17) -0.0016(16) C12 0.0237(19) 0.0162(19) 0.033(2) -0.0026(17) 0.0023(18) -0.0006(16) C13 0.0193(19) 0.023(2) 0.027(2) -0.0009(17) 0.0011(17) 0.0029(16) C14 0.025(2) 0.020(2) 0.028(2) -0.0005(18) 0.0021(18) 0.0026(17) C15 0.0237(19) 0.023(2) 0.023(2) -0.0002(17) 0.0018(18) 0.0029(17) C16 0.044(3) 0.032(3) 0.025(2) -0.005(2) -0.002(2) 0.000(2) C17 0.027(2) 0.027(2) 0.027(2) -0.0035(19) -0.0045(18) -0.0001(17) C18 0.032(2) 0.033(2) 0.026(2) -0.0020(19) -0.005(2) 0.003(2) C19 0.043(3) 0.034(3) 0.028(2) -0.004(2) -0.010(2) 0.009(2) C20 0.045(3) 0.022(2) 0.040(3) -0.001(2) -0.018(2) 0.000(2) C21 0.032(2) 0.035(3) 0.043(3) 0.004(2) -0.005(2) -0.008(2) C22 0.034(2) 0.036(3) 0.036(3) -0.007(2) -0.003(2) 0.002(2) C23 0.028(2) 0.025(2) 0.032(2) -0.004(2) 0.0006(19) -0.0020(17) C24 0.029(2) 0.059(3) 0.075(4) -0.032(3) 0.020(3) -0.011(2) C25 0.086(4) 0.041(3) 0.051(3) 0.000(3) 0.032(3) -0.003(3) C26 0.026(2) 0.037(2) 0.026(2) -0.0075(19) 0.0075(19) -0.0020(19) C27 0.032(2) 0.033(3) 0.032(2) 0.003(2) 0.004(2) 0.001(2) C28 0.045(3) 0.039(3) 0.036(3) -0.012(2) 0.000(2) -0.009(2) C29 0.044(3) 0.031(3) 0.051(3) -0.009(2) 0.011(3) 0.000(2) C30 0.039(3) 0.034(3) 0.045(3) 0.004(2) 0.005(2) -0.001(2) C31 0.025(2) 0.047(3) 0.036(3) -0.002(2) -0.0002(19) -0.003(2) C32 0.032(2) 0.021(2) 0.043(3) 0.002(2) -0.003(2) 0.0047(18) C33 0.034(2) 0.029(2) 0.035(3) 0.006(2) 0.007(2) 0.0014(19) _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 Si1 C23 1.881(4) . ? Si1 C24 1.856(5) . ? Si1 C25 1.836(5) . ? Si1 C26 1.865(4) . ? O1 N1 1.417(4) . ? O1 C15 1.350(5) . ? O2 C1 1.339(5) . ? O2 C16 1.458(5) . ? O3 C3 1.258(4) . ? O4 H4O 0.8400 . ? O4 C5 1.329(5) . ? N1 C1 1.308(5) . ? N2 H2N 0.8811 . ? N2 C14 1.509(5) . ? N2 C32 1.486(5) . ? N2 C33 1.484(5) . ? C1 C2 1.412(6) . ? C2 C3 1.459(5) . ? C2 C15 1.324(5) . ? C3 C4 1.428(5) . ? C4 C5 1.360(6) . ? C4 C13 1.507(5) . ? C5 C6 1.481(6) . ? C6 H6A 1.0000 . ? C6 C7 1.577(5) . ? C6 C11 1.545(6) . ? C7 H7A 1.0000 . ? C7 C8 1.511(6) . ? C7 C23 1.515(6) . ? C8 H8A 0.9500 . ? C8 C9 1.304(6) . ? C9 H9A 0.9500 . ? C9 C10 1.503(6) . ? C10 H10A 1.0000 . ? C10 C11 1.563(5) . ? C10 C23 1.538(6) . ? C11 H11A 1.0000 . ? C11 C12 1.518(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.533(5) . ? C13 H13A 1.0000 . ? C13 C14 1.540(5) . ? C14 H14A 1.0000 . ? C14 C15 1.490(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C17 1.494(6) . ? C17 C18 1.379(6) . ? C17 C22 1.389(6) . ? C18 H18A 0.9500 . ? C18 C19 1.379(6) . ? C19 H19A 0.9500 . ? C19 C20 1.373(7) . ? C20 H20A 0.9500 . ? C20 C21 1.367(7) . ? C21 H21A 0.9500 . ? C21 C22 1.386(6) . ? C22 H22A 0.9500 . ? C23 H23A 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.392(6) . ? C26 C31 1.402(6) . ? C27 H27A 0.9500 . ? C27 C28 1.381(6) . ? C28 H28A 0.9500 . ? C28 C29 1.374(7) . ? C29 H29A 0.9500 . ? C29 C30 1.384(7) . ? C30 H30A 0.9500 . ? C30 C31 1.384(6) . ? C31 H31A 0.9500 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 C24 Si1 C23 114.8(2) . . ? C24 Si1 C26 109.2(2) . . ? C25 Si1 C23 106.7(2) . . ? C25 Si1 C24 109.2(3) . . ? C25 Si1 C26 110.7(2) . . ? C26 Si1 C23 106.23(18) . . ? C15 O1 N1 107.9(3) . . ? C1 O2 C16 115.0(3) . . ? C5 O4 H4O 109.5 . . ? C1 N1 O1 104.3(3) . . ? C14 N2 H2N 123.4 . . ? C32 N2 H2N 95.2 . . ? C32 N2 C14 114.5(3) . . ? C33 N2 H2N 99.8 . . ? C33 N2 C14 111.3(3) . . ? C33 N2 C32 111.0(3) . . ? O2 C1 C2 125.0(4) . . ? N1 C1 O2 122.3(4) . . ? N1 C1 C2 112.7(3) . . ? C1 C2 C3 134.6(4) . . ? C15 C2 C1 104.0(3) . . ? C15 C2 C3 121.4(4) . . ? O3 C3 C2 120.7(4) . . ? O3 C3 C4 123.2(4) . . ? C4 C3 C2 116.1(3) . . ? C3 C4 C13 119.9(3) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 C13 120.0(3) . . ? O4 C5 C4 121.8(4) . . ? O4 C5 C6 112.6(4) . . ? C4 C5 C6 125.5(4) . . ? C5 C6 H6A 109.3 . . ? C5 C6 C7 110.6(3) . . ? C5 C6 C11 115.4(3) . . ? C7 C6 H6A 109.3 . . ? C11 C6 H6A 109.3 . . ? C11 C6 C7 102.8(3) . . ? C6 C7 H7A 115.9 . . ? C8 C7 C6 105.3(3) . . ? C8 C7 H7A 115.9 . . ? C8 C7 C23 101.0(3) . . ? C23 C7 C6 100.6(3) . . ? C23 C7 H7A 115.9 . . ? C7 C8 H8A 126.5 . . ? C9 C8 C7 107.1(4) . . ? C9 C8 H8A 126.5 . . ? C8 C9 H9A 125.9 . . ? C8 C9 C10 108.2(4) . . ? C10 C9 H9A 125.9 . . ? C9 C10 H10A 115.6 . . ? C9 C10 C11 108.0(3) . . ? C9 C10 C23 100.0(3) . . ? C11 C10 H10A 115.6 . . ? C23 C10 H10A 115.6 . . ? C23 C10 C11 99.9(3) . . ? C6 C11 C10 101.9(3) . . ? C6 C11 H11A 107.2 . . ? C10 C11 H11A 107.2 . . ? C12 C11 C6 114.7(3) . . ? C12 C11 C10 117.9(3) . . ? C12 C11 H11A 107.2 . . ? C11 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C11 C12 C13 114.8(3) . . ? H12A C12 H12B 107.5 . . ? C13 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C4 C13 C12 111.2(3) . . ? C4 C13 H13A 105.6 . . ? C4 C13 C14 116.8(3) . . ? C12 C13 H13A 105.6 . . ? C12 C13 C14 111.1(3) . . ? C14 C13 H13A 105.6 . . ? N2 C14 C13 115.6(3) . . ? N2 C14 H14A 107.8 . . ? C13 C14 H14A 107.8 . . ? C15 C14 N2 110.8(3) . . ? C15 C14 C13 106.7(3) . . ? C15 C14 H14A 107.8 . . ? O1 C15 C14 120.9(3) . . ? C2 C15 O1 111.1(3) . . ? C2 C15 C14 128.1(4) . . ? O2 C16 H16A 110.1 . . ? O2 C16 H16B 110.1 . . ? O2 C16 C17 108.1(3) . . ? H16A C16 H16B 108.4 . . ? C17 C16 H16A 110.1 . . ? C17 C16 H16B 110.1 . . ? C18 C17 C16 120.3(4) . . ? C18 C17 C22 119.7(4) . . ? C22 C17 C16 119.9(4) . . ? C17 C18 H18A 120.1 . . ? C17 C18 C19 119.8(4) . . ? C19 C18 H18A 120.1 . . ? C18 C19 H19A 120.0 . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19A 120.0 . . ? C19 C20 H20A 119.4 . . ? C21 C20 C19 121.1(4) . . ? C21 C20 H20A 119.4 . . ? C20 C21 H21A 120.4 . . ? C20 C21 C22 119.2(5) . . ? C22 C21 H21A 120.4 . . ? C17 C22 H22A 119.9 . . ? C21 C22 C17 120.1(4) . . ? C21 C22 H22A 119.9 . . ? Si1 C23 H23A 108.6 . . ? C7 C23 Si1 118.8(3) . . ? C7 C23 C10 93.2(3) . . ? C7 C23 H23A 108.6 . . ? C10 C23 Si1 118.1(3) . . ? C10 C23 H23A 108.6 . . ? Si1 C24 H24A 109.5 . . ? Si1 C24 H24B 109.5 . . ? Si1 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Si1 C25 H25A 109.5 . . ? Si1 C25 H25B 109.5 . . ? Si1 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 Si1 121.0(3) . . ? C27 C26 C31 117.1(4) . . ? C31 C26 Si1 121.8(3) . . ? C26 C27 H27A 119.4 . . ? C28 C27 C26 121.2(4) . . ? C28 C27 H27A 119.4 . . ? C27 C28 H28A 119.6 . . ? C29 C28 C27 120.8(4) . . ? C29 C28 H28A 119.6 . . ? C28 C29 H29A 120.3 . . ? C28 C29 C30 119.5(4) . . ? C30 C29 H29A 120.3 . . ? C29 C30 H30A 120.1 . . ? C29 C30 C31 119.8(5) . . ? C31 C30 H30A 120.1 . . ? C26 C31 H31A 119.2 . . ? C30 C31 C26 121.6(4) . . ? C30 C31 H31A 119.2 . . ? N2 C32 H32A 109.5 . . ? N2 C32 H32B 109.5 . . ? N2 C32 H32C 109.5 . . ? H32A C32 H32B 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N2 C33 H33A 109.5 . . ? N2 C33 H33B 109.5 . . ? N2 C33 H33C 109.5 . . ? H33A C33 H33B 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? 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 O4 H4O O3 0.84 1.80 2.510(4) 141.8 . N2 H2N Cl1 0.88 2.12 2.993(3) 173.3 3_556 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 Si1 C26 C27 C28 178.1(3) . . . . ? Si1 C26 C31 C30 -178.5(3) . . . . ? O1 N1 C1 O2 179.6(3) . . . . ? O1 N1 C1 C2 0.0(4) . . . . ? O2 C1 C2 C3 2.7(7) . . . . ? O2 C1 C2 C15 -179.8(4) . . . . ? O2 C16 C17 C18 -123.9(4) . . . . ? O2 C16 C17 C22 57.9(5) . . . . ? O3 C3 C4 C5 -1.7(6) . . . . ? O3 C3 C4 C13 -172.2(4) . . . . ? O4 C5 C6 C7 -70.7(4) . . . . ? O4 C5 C6 C11 173.2(3) . . . . ? N1 O1 C15 C2 -0.3(5) . . . . ? N1 O1 C15 C14 179.1(3) . . . . ? N1 C1 C2 C3 -177.7(4) . . . . ? N1 C1 C2 C15 -0.2(5) . . . . ? N2 C14 C15 O1 -75.3(5) . . . . ? N2 C14 C15 C2 104.0(5) . . . . ? C1 O2 C16 C17 -174.2(3) . . . . ? C1 C2 C3 O3 6.5(7) . . . . ? C1 C2 C3 C4 -172.1(4) . . . . ? C1 C2 C15 O1 0.3(5) . . . . ? C1 C2 C15 C14 -179.1(4) . . . . ? C2 C3 C4 C5 176.8(4) . . . . ? C2 C3 C4 C13 6.3(5) . . . . ? C3 C2 C15 O1 178.2(4) . . . . ? C3 C2 C15 C14 -1.1(7) . . . . ? C3 C4 C5 O4 6.4(6) . . . . ? C3 C4 C5 C6 -169.1(4) . . . . ? C3 C4 C13 C12 -160.9(3) . . . . ? C3 C4 C13 C14 -32.0(5) . . . . ? C4 C5 C6 C7 105.2(5) . . . . ? C4 C5 C6 C11 -10.9(6) . . . . ? C4 C13 C14 N2 -86.8(4) . . . . ? C4 C13 C14 C15 36.9(4) . . . . ? C5 C4 C13 C12 28.7(5) . . . . ? C5 C4 C13 C14 157.6(4) . . . . ? C5 C6 C7 C8 -54.1(4) . . . . ? C5 C6 C7 C23 -158.7(3) . . . . ? C5 C6 C11 C10 117.3(4) . . . . ? C5 C6 C11 C12 -11.2(5) . . . . ? C6 C7 C8 C9 -71.1(4) . . . . ? C6 C7 C23 Si1 -177.1(3) . . . . ? C6 C7 C23 C10 58.3(3) . . . . ? C6 C11 C12 C13 41.4(5) . . . . ? C7 C6 C11 C10 -3.1(4) . . . . ? C7 C6 C11 C12 -131.6(4) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C8 C7 C23 Si1 74.9(4) . . . . ? C8 C7 C23 C10 -49.8(3) . . . . ? C8 C9 C10 C11 70.2(4) . . . . ? C8 C9 C10 C23 -33.7(4) . . . . ? C9 C10 C11 C6 -64.5(4) . . . . ? C9 C10 C11 C12 62.0(5) . . . . ? C9 C10 C23 Si1 -75.3(4) . . . . ? C9 C10 C23 C7 49.9(3) . . . . ? C10 C11 C12 C13 -78.6(4) . . . . ? C11 C6 C7 C8 69.6(4) . . . . ? C11 C6 C7 C23 -35.0(4) . . . . ? C11 C10 C23 Si1 174.2(3) . . . . ? C11 C10 C23 C7 -60.6(3) . . . . ? C11 C12 C13 C4 -49.8(4) . . . . ? C11 C12 C13 C14 178.3(3) . . . . ? C12 C13 C14 N2 42.1(4) . . . . ? C12 C13 C14 C15 165.8(3) . . . . ? C13 C4 C5 O4 176.9(3) . . . . ? C13 C4 C5 C6 1.3(6) . . . . ? C13 C14 C15 O1 158.1(3) . . . . ? C13 C14 C15 C2 -22.6(6) . . . . ? C15 O1 N1 C1 0.2(4) . . . . ? C15 C2 C3 O3 -170.7(4) . . . . ? C15 C2 C3 C4 10.8(6) . . . . ? C16 O2 C1 N1 -4.2(5) . . . . ? C16 O2 C1 C2 175.3(4) . . . . ? C16 C17 C18 C19 -175.7(4) . . . . ? C16 C17 C22 C21 176.4(4) . . . . ? C17 C18 C19 C20 -1.4(6) . . . . ? C18 C17 C22 C21 -1.8(6) . . . . ? C18 C19 C20 C21 -0.3(6) . . . . ? C19 C20 C21 C22 1.0(7) . . . . ? C20 C21 C22 C17 0.1(7) . . . . ? C22 C17 C18 C19 2.4(6) . . . . ? C23 Si1 C26 C27 -88.2(4) . . . . ? C23 Si1 C26 C31 89.3(4) . . . . ? C23 C7 C8 C9 33.2(4) . . . . ? C23 C10 C11 C6 39.6(4) . . . . ? C23 C10 C11 C12 166.0(3) . . . . ? C24 Si1 C23 C7 -49.6(4) . . . . ? C24 Si1 C23 C10 61.8(4) . . . . ? C24 Si1 C26 C27 147.5(4) . . . . ? C24 Si1 C26 C31 -35.0(4) . . . . ? C25 Si1 C23 C7 71.5(4) . . . . ? C25 Si1 C23 C10 -177.1(3) . . . . ? C25 Si1 C26 C27 27.2(4) . . . . ? C25 Si1 C26 C31 -155.3(4) . . . . ? C26 Si1 C23 C7 -170.4(3) . . . . ? C26 Si1 C23 C10 -59.0(4) . . . . ? C26 C27 C28 C29 0.6(7) . . . . ? C27 C26 C31 C30 -0.9(6) . . . . ? C27 C28 C29 C30 -1.4(7) . . . . ? C28 C29 C30 C31 0.9(7) . . . . ? C29 C30 C31 C26 0.2(7) . . . . ? C31 C26 C27 C28 0.5(6) . . . . ? C32 N2 C14 C13 68.5(4) . . . . ? C32 N2 C14 C15 -53.0(4) . . . . ? C33 N2 C14 C13 -164.6(3) . . . . ? C33 N2 C14 C15 73.9(4) . . . . ? # Attachment '- by-product in ref 19.cif' data_AD-1-290-impunety _database_code_depnum_ccdc_archive 'CCDC 826312' #TrackingRef '- by-product in ref 19.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N2 O4' _chemical_formula_weight 350.36 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 8.4645(18) _cell_length_b 9.265(2) _cell_length_c 13.880(3) _cell_angle_alpha 101.300(15) _cell_angle_beta 98.534(14) _cell_angle_gamma 106.220(14) _cell_volume 1000.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1308 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 20.26 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9870 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 11619 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.1498 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.06 _reflns_number_total 3833 _reflns_number_gt 1391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX II (Bruker, 2007)' _computing_cell_refinement 'Bruker Saint v7.23A (Bruker, 2005)' _computing_data_reduction 'Bruker Saint v7.23A (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. The data is week and the possible disorder solvent can not be located. ; _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^)+(0.0136P)^2^+1.6470P] 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 3833 _refine_ls_number_parameters 287 _refine_ls_number_restraints 289 _refine_ls_R_factor_all 0.1916 _refine_ls_R_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.1873 _refine_ls_wR_factor_gt 0.1646 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 0.967 _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 -0.0390(4) 0.1222(4) 0.4260(2) 0.0461(10) Uani 1 1 d . A . O2 O -0.1231(4) 0.2710(4) 0.3077(2) 0.0462(10) Uani 1 1 d . . . H2O H -0.1080 0.2605 0.3771 0.055 Uiso 1 1 d R . . N1 N 0.0990(5) -0.0424(5) 0.3902(3) 0.0516(13) Uani 1 1 d . A . H1NA H 0.0867 -0.0943 0.4382 0.062 Uiso 1 1 d R . . H1NB H 0.1568 -0.0686 0.3505 0.062 Uiso 1 1 d R . . N2 N -0.0937(6) 0.3863(5) 0.1405(3) 0.0460(12) Uani 1 1 d . . . C1 C 0.0537(6) 0.1150(6) 0.2755(3) 0.0355(13) Uani 1 1 d . A . C2 C -0.0264(6) 0.2199(6) 0.2480(4) 0.0375(13) Uani 1 1 d . . . C3 C -0.0131(6) 0.2754(6) 0.1666(4) 0.0394(13) Uani 1 1 d . . . C4 C 0.0865(6) 0.2268(6) 0.1000(3) 0.0351(12) Uani 1 1 d . . . C5 C 0.1059(6) 0.2752(6) 0.0130(3) 0.0407(13) Uani 1 1 d . . . H5A H 0.0501 0.3444 -0.0060 0.049 Uiso 1 1 calc R . . C6 C 0.2046(7) 0.2241(6) -0.0458(4) 0.0456(14) Uani 1 1 d . . . H6A H 0.2160 0.2586 -0.1053 0.055 Uiso 1 1 calc R . . C7 C 0.2890(7) 0.1231(6) -0.0211(4) 0.0501(16) Uani 1 1 d . A . H7A H 0.3567 0.0878 -0.0630 0.060 Uiso 1 1 calc R . . C8 C 0.2723(6) 0.0769(6) 0.0634(4) 0.0409(13) Uani 1 1 d . . . C9 C 0.1716(6) 0.1252(6) 0.1270(4) 0.0361(13) Uani 1 1 d . A . C10 C 0.1506(6) 0.0690(6) 0.2111(4) 0.0372(13) Uani 1 1 d . . . C11 C 0.0378(6) 0.0648(6) 0.3663(4) 0.0399(13) Uani 1 1 d . . . C12 C -0.2747(7) 0.3244(7) 0.1164(4) 0.0566(16) Uani 1 1 d . . . H12A H -0.3221 0.4038 0.0997 0.085 Uiso 1 1 calc R . . H12B H -0.3143 0.2935 0.1745 0.085 Uiso 1 1 calc R . . H12C H -0.3111 0.2338 0.0587 0.085 Uiso 1 1 calc R . . C13 C -0.0290(7) 0.5341(6) 0.2142(4) 0.0555(16) Uani 1 1 d . . . H13A H -0.0868 0.6051 0.1940 0.083 Uiso 1 1 calc R . . H13B H 0.0922 0.5784 0.2187 0.083 Uiso 1 1 calc R . . H13C H -0.0486 0.5193 0.2800 0.083 Uiso 1 1 calc R . . O3 O 0.329(3) -0.043(3) 0.0800(13) 0.041(3) Uani 0.363(9) 1 d PDU A 1 O4 O 0.248(4) -0.031(6) 0.241(2) 0.036(3) Uani 0.363(9) 1 d PDU A 1 C14 C 0.289(2) -0.104(2) 0.1498(11) 0.0393(14) Uani 0.363(9) 1 d PDU A 1 H14A H 0.1810 -0.1874 0.1152 0.047 Uiso 0.363(9) 1 calc PR A 1 C15 C 0.3957(17) -0.1922(15) 0.1852(11) 0.040(2) Uani 0.363(9) 1 d PGDU A 1 C16 C 0.3571(17) -0.3516(15) 0.1490(11) 0.044(3) Uani 0.363(9) 1 d PGU A 1 H16A H 0.2611 -0.4079 0.0964 0.053 Uiso 0.363(9) 1 calc PR A 1 C17 C 0.459(2) -0.4288(11) 0.1897(14) 0.046(3) Uani 0.363(9) 1 d PGU A 1 H17A H 0.4325 -0.5378 0.1650 0.056 Uiso 0.363(9) 1 calc PR A 1 C18 C 0.599(2) -0.3466(16) 0.2666(15) 0.047(3) Uani 0.363(9) 1 d PGU A 1 H18A H 0.6690 -0.3993 0.2945 0.056 Uiso 0.363(9) 1 calc PR A 1 C19 C 0.6380(18) -0.1871(16) 0.3028(12) 0.047(3) Uani 0.363(9) 1 d PGU A 1 H19A H 0.7340 -0.1309 0.3554 0.057 Uiso 0.363(9) 1 calc PR A 1 C20 C 0.5362(19) -0.1099(11) 0.2621(11) 0.041(3) Uani 0.363(9) 1 d PGU A 1 H20A H 0.5626 -0.0010 0.2868 0.049 Uiso 0.363(9) 1 calc PR A 1 O3' O 0.3662(16) -0.0114(15) 0.0985(7) 0.040(2) Uani 0.637(9) 1 d PDU A 2 O4' O 0.230(2) -0.033(4) 0.2272(11) 0.033(2) Uani 0.637(9) 1 d PDU A 2 C14' C 0.3844(12) -0.0157(12) 0.1909(7) 0.0393(14) Uani 0.637(9) 1 d PDU A 2 H14B H 0.4690 0.0845 0.2319 0.047 Uiso 0.637(9) 1 calc PR A 2 C15' C 0.4480(11) -0.1438(8) 0.2102(6) 0.0388(17) Uani 0.637(9) 1 d PGDU A 2 C16' C 0.3753(10) -0.2958(9) 0.1523(6) 0.046(2) Uani 0.637(9) 1 d PGU A 2 H16B H 0.2826 -0.3206 0.0975 0.055 Uiso 0.637(9) 1 calc PR A 2 C17' C 0.4385(12) -0.4115(7) 0.1747(7) 0.047(2) Uani 0.637(9) 1 d PGU A 2 H17B H 0.3889 -0.5153 0.1352 0.057 Uiso 0.637(9) 1 calc PR A 2 C18' C 0.5743(12) -0.3751(7) 0.2550(8) 0.049(2) Uani 0.637(9) 1 d PGU A 2 H18B H 0.6175 -0.4542 0.2703 0.059 Uiso 0.637(9) 1 calc PR A 2 C19' C 0.6469(10) -0.2232(9) 0.3128(6) 0.046(2) Uani 0.637(9) 1 d PGU A 2 H19B H 0.7397 -0.1983 0.3677 0.055 Uiso 0.637(9) 1 calc PR A 2 C20' C 0.5837(10) -0.1075(6) 0.2904(6) 0.046(2) Uani 0.637(9) 1 d PGU A 2 H20B H 0.6334 -0.0037 0.3300 0.055 Uiso 0.637(9) 1 calc PR A 2 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 0.062(2) 0.064(3) 0.041(2) 0.0276(18) 0.0337(18) 0.043(2) O2 0.061(3) 0.070(3) 0.038(2) 0.0270(19) 0.0321(18) 0.050(2) N1 0.068(3) 0.081(3) 0.047(3) 0.044(3) 0.041(2) 0.053(3) N2 0.057(3) 0.066(3) 0.042(3) 0.025(2) 0.025(2) 0.046(3) C1 0.047(3) 0.051(3) 0.030(3) 0.024(2) 0.022(2) 0.033(3) C2 0.037(3) 0.049(4) 0.038(3) 0.013(3) 0.020(2) 0.023(3) C3 0.048(3) 0.055(4) 0.038(3) 0.023(3) 0.022(3) 0.037(3) C4 0.043(3) 0.048(3) 0.029(3) 0.019(2) 0.017(2) 0.027(3) C5 0.057(4) 0.051(4) 0.031(3) 0.017(3) 0.018(3) 0.034(3) C6 0.066(4) 0.063(4) 0.031(3) 0.026(3) 0.025(3) 0.040(3) C7 0.063(4) 0.078(4) 0.046(3) 0.035(3) 0.034(3) 0.053(4) C8 0.041(3) 0.055(4) 0.043(3) 0.020(3) 0.019(3) 0.030(3) C9 0.040(3) 0.044(3) 0.037(3) 0.019(3) 0.019(2) 0.023(3) C10 0.038(3) 0.048(3) 0.040(3) 0.024(3) 0.017(2) 0.024(3) C11 0.043(3) 0.055(4) 0.035(3) 0.019(3) 0.018(2) 0.025(3) C12 0.066(4) 0.075(4) 0.052(4) 0.021(3) 0.020(3) 0.053(4) C13 0.062(4) 0.060(4) 0.074(4) 0.040(3) 0.030(3) 0.043(3) O3 0.049(6) 0.063(6) 0.031(5) 0.020(4) 0.019(4) 0.039(5) O4 0.043(5) 0.053(5) 0.040(5) 0.025(6) 0.024(5) 0.040(5) C14 0.046(3) 0.058(3) 0.036(3) 0.023(3) 0.024(3) 0.036(2) C15 0.049(4) 0.055(4) 0.041(4) 0.024(4) 0.029(4) 0.036(4) C16 0.056(5) 0.056(5) 0.046(4) 0.030(4) 0.025(4) 0.038(4) C17 0.049(5) 0.059(4) 0.054(5) 0.029(4) 0.019(4) 0.039(4) C18 0.050(4) 0.055(4) 0.057(4) 0.026(4) 0.022(4) 0.037(4) C19 0.051(4) 0.054(4) 0.057(4) 0.029(4) 0.018(4) 0.035(4) C20 0.048(5) 0.053(4) 0.045(5) 0.027(4) 0.023(4) 0.037(4) O3' 0.049(5) 0.066(5) 0.032(4) 0.023(4) 0.023(3) 0.044(4) O4' 0.044(4) 0.050(3) 0.032(4) 0.026(4) 0.022(4) 0.036(4) C14' 0.046(3) 0.058(3) 0.036(3) 0.023(3) 0.024(3) 0.036(2) C15' 0.045(4) 0.055(3) 0.040(4) 0.027(3) 0.025(3) 0.035(3) C16' 0.054(4) 0.056(4) 0.050(4) 0.026(4) 0.025(3) 0.038(4) C17' 0.051(4) 0.060(3) 0.053(4) 0.029(3) 0.021(3) 0.038(3) C18' 0.051(4) 0.058(4) 0.059(4) 0.024(3) 0.022(3) 0.037(3) C19' 0.052(4) 0.049(4) 0.060(4) 0.027(3) 0.018(3) 0.038(3) C20' 0.054(4) 0.052(4) 0.055(4) 0.027(3) 0.019(3) 0.040(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 C11 1.254(5) . ? O2 C2 1.359(5) . ? O2 H2O 0.9802 . ? N1 C11 1.316(6) . ? N1 H1NA 0.8961 . ? N1 H1NB 0.8350 . ? N2 C12 1.439(6) . ? N2 C13 1.445(6) . ? N2 C3 1.455(6) . ? C1 C10 1.385(6) . ? C1 C2 1.410(6) . ? C1 C11 1.438(6) . ? C2 C3 1.336(6) . ? C3 C4 1.432(6) . ? C4 C5 1.385(6) . ? C4 C9 1.408(6) . ? C5 C6 1.363(6) . ? C5 H5A 0.9500 . ? C6 C7 1.390(6) . ? C6 H6A 0.9500 . ? C7 C8 1.338(6) . ? C7 H7A 0.9500 . ? C8 O3 1.37(3) . ? C8 O3' 1.394(16) . ? C8 C9 1.410(6) . ? C9 C10 1.382(6) . ? C10 O4' 1.33(3) . ? C10 O4 1.48(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O3 C14 1.253(14) . ? O4 C14 1.458(18) . ? C14 C15 1.470(12) . ? C14 H14A 1.0000 . ? C15 C16 1.3900 . ? C15 C20 1.3900 . ? C16 C17 1.3900 . ? C16 H16A 0.9500 . ? C17 C18 1.3900 . ? C17 H17A 0.9500 . ? C18 C19 1.3900 . ? C18 H18A 0.9500 . ? C19 C20 1.3900 . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? O3' C14' 1.278(9) . ? O4' C14' 1.451(15) . ? C14' C15' 1.486(7) . ? C14' H14B 1.0000 . ? C15' C16' 1.3900 . ? C15' C20' 1.3900 . ? C16' C17' 1.3900 . ? C16' H16B 0.9500 . ? C17' C18' 1.3900 . ? C17' H17B 0.9500 . ? C18' C19' 1.3900 . ? C18' H18B 0.9500 . ? C19' C20' 1.3900 . ? C19' H19B 0.9500 . ? C20' H20B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O2 H2O 118.6 . . ? C11 N1 H1NA 132.8 . . ? C11 N1 H1NB 111.9 . . ? H1NA N1 H1NB 115.3 . . ? C12 N2 C13 113.5(4) . . ? C12 N2 C3 113.0(4) . . ? C13 N2 C3 112.1(4) . . ? C10 C1 C2 115.3(4) . . ? C10 C1 C11 123.5(4) . . ? C2 C1 C11 121.2(4) . . ? C3 C2 O2 116.6(4) . . ? C3 C2 C1 124.6(4) . . ? O2 C2 C1 118.8(4) . . ? C2 C3 C4 119.8(4) . . ? C2 C3 N2 123.8(4) . . ? C4 C3 N2 116.3(4) . . ? C5 C4 C9 118.8(4) . . ? C5 C4 C3 124.3(4) . . ? C9 C4 C3 116.9(4) . . ? C6 C5 C4 120.5(4) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C5 C6 C7 121.8(5) . . ? C5 C6 H6A 119.1 . . ? C7 C6 H6A 119.1 . . ? C8 C7 C6 118.1(5) . . ? C8 C7 H7A 120.9 . . ? C6 C7 H7A 120.9 . . ? C7 C8 O3 118.9(9) . . ? C7 C8 O3' 121.5(6) . . ? C7 C8 C9 122.7(4) . . ? O3 C8 C9 117.3(9) . . ? O3' C8 C9 115.6(6) . . ? C10 C9 C4 120.8(4) . . ? C10 C9 C8 121.1(4) . . ? C4 C9 C8 118.1(4) . . ? O4' C10 C9 116.1(7) . . ? O4' C10 C1 121.3(7) . . ? C9 C10 C1 122.5(4) . . ? C9 C10 O4 120.0(11) . . ? C1 C10 O4 117.1(10) . . ? O1 C11 N1 117.1(4) . . ? O1 C11 C1 120.1(4) . . ? N1 C11 C1 122.8(5) . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C14 O3 C8 119(2) . . ? C14 O4 C10 106(2) . . ? O3 C14 O4 127(3) . . ? O3 C14 C15 115.9(18) . . ? O4 C14 C15 104(2) . . ? O3 C14 H14A 102.2 . . ? O4 C14 H14A 102.2 . . ? C15 C14 H14A 102.2 . . ? C16 C15 C20 120.0 . . ? C16 C15 C14 123.2(11) . . ? C20 C15 C14 116.7(11) . . ? C15 C16 C17 120.0 . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C18 C17 C16 120.0 . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 C19 120.0 . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C20 120.0 . . ? C18 C19 H19A 120.0 . . ? C20 C19 H19A 120.0 . . ? C19 C20 C15 120.0 . . ? C19 C20 H20A 120.0 . . ? C15 C20 H20A 120.0 . . ? C14' O3' C8 119.3(11) . . ? C10 O4' C14' 116(2) . . ? O3' C14' O4' 113.0(11) . . ? O3' C14' C15' 112.4(9) . . ? O4' C14' C15' 107.7(14) . . ? O3' C14' H14B 107.9 . . ? O4' C14' H14B 107.9 . . ? C15' C14' H14B 107.9 . . ? C16' C15' C20' 120.0 . . ? C16' C15' C14' 122.5(6) . . ? C20' C15' C14' 117.5(6) . . ? C15' C16' C17' 120.0 . . ? C15' C16' H16B 120.0 . . ? C17' C16' H16B 120.0 . . ? C18' C17' C16' 120.0 . . ? C18' C17' H17B 120.0 . . ? C16' C17' H17B 120.0 . . ? C17' C18' C19' 120.0 . . ? C17' C18' H18B 120.0 . . ? C19' C18' H18B 120.0 . . ? C20' C19' C18' 120.0 . . ? C20' C19' H19B 120.0 . . ? C18' C19' H19B 120.0 . . ? C19' C20' C15' 120.0 . . ? C19' C20' H20B 120.0 . . ? C15' C20' H20B 120.0 . . ? 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 C10 C1 C2 C3 -0.4(8) . . . . ? C11 C1 C2 C3 177.8(5) . . . . ? C10 C1 C2 O2 -179.7(5) . . . . ? C11 C1 C2 O2 -1.5(7) . . . . ? O2 C2 C3 C4 -179.9(5) . . . . ? C1 C2 C3 C4 0.8(8) . . . . ? O2 C2 C3 N2 0.7(8) . . . . ? C1 C2 C3 N2 -178.6(5) . . . . ? C12 N2 C3 C2 -65.3(7) . . . . ? C13 N2 C3 C2 64.5(7) . . . . ? C12 N2 C3 C4 115.3(5) . . . . ? C13 N2 C3 C4 -114.9(5) . . . . ? C2 C3 C4 C5 178.8(5) . . . . ? N2 C3 C4 C5 -1.8(8) . . . . ? C2 C3 C4 C9 -2.3(7) . . . . ? N2 C3 C4 C9 177.1(5) . . . . ? C9 C4 C5 C6 0.5(7) . . . . ? C3 C4 C5 C6 179.4(5) . . . . ? C4 C5 C6 C7 -0.1(8) . . . . ? C5 C6 C7 C8 -0.5(8) . . . . ? C6 C7 C8 O3 168.5(11) . . . . ? C6 C7 C8 O3' -173.4(7) . . . . ? C6 C7 C8 C9 0.7(8) . . . . ? C5 C4 C9 C10 -177.4(5) . . . . ? C3 C4 C9 C10 3.6(7) . . . . ? C5 C4 C9 C8 -0.3(7) . . . . ? C3 C4 C9 C8 -179.3(5) . . . . ? C7 C8 C9 C10 176.7(5) . . . . ? O3 C8 C9 C10 8.8(12) . . . . ? O3' C8 C9 C10 -8.8(8) . . . . ? C7 C8 C9 C4 -0.4(8) . . . . ? O3 C8 C9 C4 -168.3(10) . . . . ? O3' C8 C9 C4 174.1(7) . . . . ? C4 C9 C10 O4' 176.6(13) . . . . ? C8 C9 C10 O4' -0.5(14) . . . . ? C4 C9 C10 C1 -3.5(8) . . . . ? C8 C9 C10 C1 179.5(5) . . . . ? C4 C9 C10 O4 -177(2) . . . . ? C8 C9 C10 O4 6(2) . . . . ? C2 C1 C10 O4' -178.3(13) . . . . ? C11 C1 C10 O4' 3.5(15) . . . . ? C2 C1 C10 C9 1.8(7) . . . . ? C11 C1 C10 C9 -176.4(5) . . . . ? C2 C1 C10 O4 175(2) . . . . ? C11 C1 C10 O4 -3(2) . . . . ? C10 C1 C11 O1 173.3(5) . . . . ? C2 C1 C11 O1 -4.8(8) . . . . ? C10 C1 C11 N1 -7.7(8) . . . . ? C2 C1 C11 N1 174.2(5) . . . . ? C7 C8 O3 C14 -168.3(15) . . . . ? C9 C8 O3 C14 0(2) . . . . ? C9 C10 O4 C14 -25(4) . . . . ? C1 C10 O4 C14 161.2(18) . . . . ? C8 O3 C14 O4 -27(3) . . . . ? C8 O3 C14 C15 -160.5(14) . . . . ? C10 O4 C14 O3 38(4) . . . . ? C10 O4 C14 C15 176(2) . . . . ? O3 C14 C15 C16 -94(2) . . . . ? O4 C14 C15 C16 122(2) . . . . ? O3 C14 C15 C20 89.1(19) . . . . ? O4 C14 C15 C20 -55(2) . . . . ? C20 C15 C16 C17 0.0 . . . . ? C14 C15 C16 C17 -176.6(16) . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C19 C20 C15 0.0 . . . . ? C16 C15 C20 C19 0.0 . . . . ? C14 C15 C20 C19 176.9(15) . . . . ? C7 C8 O3' C14' 160.0(8) . . . . ? C9 C8 O3' C14' -14.5(12) . . . . ? C9 C10 O4' C14' 29.5(19) . . . . ? C1 C10 O4' C14' -150.4(10) . . . . ? C8 O3' C14' O4' 43.2(17) . . . . ? C8 O3' C14' C15' 165.3(8) . . . . ? C10 O4' C14' O3' -52(2) . . . . ? C10 O4' C14' C15' -176.8(12) . . . . ? O3' C14' C15' C16' -49.9(11) . . . . ? O4' C14' C15' C16' 75.2(12) . . . . ? O3' C14' C15' C20' 131.1(9) . . . . ? O4' C14' C15' C20' -103.9(11) . . . . ? C20' C15' C16' C17' 0.0 . . . . ? C14' C15' C16' C17' -179.0(9) . . . . ? C15' C16' C17' C18' 0.0 . . . . ? C16' C17' C18' C19' 0.0 . . . . ? C17' C18' C19' C20' 0.0 . . . . ? C18' C19' C20' C15' 0.0 . . . . ? C16' C15' C20' C19' 0.0 . . . . ? C14' C15' C20' C19' 179.1(8) . . . . ? 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 H2O O1 0.98 1.76 2.488(4) 128.5 . N1 H1NA O1 0.90 2.04 2.868(5) 154.0 2_556 N1 H1NB O4 0.83 1.85 2.58(2) 145.4 . N1 H1NB O4' 0.83 1.96 2.669(14) 142.1 . _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.236 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.070 # Attachment '- compound 13.cif' data_RDP _database_code_depnum_ccdc_archive 'CCDC 826313' #TrackingRef '- compound 13.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N2 O4' _chemical_formula_weight 352.38 _chemical_absolute_configuration ad _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _cell_length_a 6.4713(2) _cell_length_b 12.2439(3) _cell_length_c 21.5133(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1704.58(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 39693 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 66.0 _cell_measurement_theta_min 3.11 _exptl_absorpt_coefficient_mu 0.792 _exptl_absorpt_correction_T_max 0.8706 _exptl_absorpt_correction_T_min 0.8088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 42649 _diffrn_reflns_theta_full 66.46 _diffrn_reflns_theta_max 66.46 _diffrn_reflns_theta_min 4.11 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _reflns_number_gt 2902 _reflns_number_total 2922 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.151 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(15) _refine_ls_extinction_coef 0.0045(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 242 _refine_ls_number_reflns 2922 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0256 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.2931P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.0696 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.99494(14) 0.32504(7) 0.60692(4) 0.0211(2) Uani 1 1 d . . . O2 O 0.20520(16) 0.53881(8) 0.72637(5) 0.0272(2) Uani 1 1 d . . . O3 O 0.50908(15) 0.58251(7) 0.65744(4) 0.0248(2) Uani 1 1 d . . . O4 O 0.94872(14) 0.60730(7) 0.59690(4) 0.0218(2) Uani 1 1 d . . . N1 N 1.06935(18) 0.42972(9) 0.58583(5) 0.0216(2) Uani 1 1 d . . . N2 N 0.59441(16) 0.18646(9) 0.60712(5) 0.0192(2) Uani 1 1 d . . . C1 C 0.8174(2) 0.34066(11) 0.63779(5) 0.0189(3) Uani 1 1 d . . . C2 C 0.68943(19) 0.24564(10) 0.65922(6) 0.0194(3) Uani 1 1 d . . . H2A H 0.7842 0.1936 0.6810 0.023 Uiso 1 1 calc R . . C3 C 0.5327(2) 0.28909(11) 0.70835(5) 0.0201(3) Uani 1 1 d . . . H3 H 0.6079 0.2898 0.7490 0.024 Uiso 1 1 calc R . . C4 C 0.3512(2) 0.21032(12) 0.71651(6) 0.0240(3) Uani 1 1 d . . . H4A H 0.2815 0.1995 0.6760 0.029 Uiso 1 1 calc R . . H4B H 0.4034 0.1386 0.7308 0.029 Uiso 1 1 calc R . . C5 C 0.1985(2) 0.25403(12) 0.76301(6) 0.0282(3) Uani 1 1 d . . . H5 H 0.1261 0.2047 0.7892 0.034 Uiso 1 1 calc R . . C6 C 0.1632(2) 0.36083(12) 0.76792(6) 0.0270(3) Uani 1 1 d . . . H6 H 0.0637 0.3873 0.7967 0.032 Uiso 1 1 calc R . . C7 C 0.2777(2) 0.43665(11) 0.72912(6) 0.0237(3) Uani 1 1 d . . . C8 C 0.45399(19) 0.40496(11) 0.69823(6) 0.0203(3) Uani 1 1 d . . . C9 C 0.5704(2) 0.48545(10) 0.66480(5) 0.0193(3) Uani 1 1 d . . . C10 C 0.7662(2) 0.44792(11) 0.63886(5) 0.0189(3) Uani 1 1 d . . . C11 C 0.9321(2) 0.49990(10) 0.60599(6) 0.0188(3) Uani 1 1 d . . . C12 C 1.1203(2) 0.63998(11) 0.55700(6) 0.0228(3) Uani 1 1 d . . . H12A H 1.0886 0.6219 0.5132 0.027 Uiso 1 1 calc R . . H12B H 1.2473 0.6003 0.5692 0.027 Uiso 1 1 calc R . . C13 C 1.1527(2) 0.76056(11) 0.56368(6) 0.0214(3) Uani 1 1 d . . . C14 C 1.0951(2) 0.83205(11) 0.51708(6) 0.0246(3) Uani 1 1 d . . . H14 H 1.0310 0.8046 0.4806 0.029 Uiso 1 1 calc R . . C15 C 1.1296(2) 0.94308(12) 0.52296(7) 0.0282(3) Uani 1 1 d . . . H15 H 1.0866 0.9914 0.4909 0.034 Uiso 1 1 calc R . . C16 C 1.2266(2) 0.98415(11) 0.57541(7) 0.0261(3) Uani 1 1 d . . . H16 H 1.2498 1.0604 0.5795 0.031 Uiso 1 1 calc R . . C17 C 1.2893(2) 0.91317(12) 0.62172(7) 0.0293(3) Uani 1 1 d . . . H17 H 1.3576 0.9405 0.6576 0.035 Uiso 1 1 calc R . . C18 C 1.2525(2) 0.80225(12) 0.61582(6) 0.0284(3) Uani 1 1 d . . . H18 H 1.2960 0.7540 0.6478 0.034 Uiso 1 1 calc R . . C19 C 0.5024(2) 0.25689(11) 0.55974(5) 0.0218(3) Uani 1 1 d . . . H19A H 0.6117 0.2979 0.5385 0.033 Uiso 1 1 calc R . . H19B H 0.4061 0.3080 0.5795 0.033 Uiso 1 1 calc R . . H19C H 0.4279 0.2120 0.5294 0.033 Uiso 1 1 calc R . . C20 C 0.7362(2) 0.10774(11) 0.57935(6) 0.0249(3) Uani 1 1 d . . . H20A H 0.7841 0.0566 0.6113 0.037 Uiso 1 1 calc R . . H20B H 0.8550 0.1464 0.5616 0.037 Uiso 1 1 calc R . . H20C H 0.6648 0.0673 0.5464 0.037 Uiso 1 1 calc R . . H2 H 0.302(3) 0.5757(16) 0.6998(9) 0.048(5) 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 0.0200(4) 0.0161(5) 0.0270(5) 0.0000(3) 0.0018(4) -0.0012(4) O2 0.0253(5) 0.0244(5) 0.0319(5) -0.0049(4) 0.0046(4) 0.0027(4) O3 0.0254(5) 0.0177(5) 0.0312(5) -0.0023(3) 0.0021(4) 0.0026(4) O4 0.0237(5) 0.0160(5) 0.0257(5) -0.0011(3) 0.0040(4) -0.0018(4) N1 0.0228(5) 0.0156(6) 0.0264(5) 0.0016(4) 0.0013(4) -0.0035(4) N2 0.0215(5) 0.0162(6) 0.0200(5) -0.0003(4) 0.0004(4) -0.0004(4) C1 0.0173(6) 0.0216(7) 0.0179(6) -0.0016(5) -0.0021(5) 0.0005(5) C2 0.0205(6) 0.0162(7) 0.0213(6) 0.0022(5) -0.0018(5) 0.0009(5) C3 0.0224(7) 0.0216(7) 0.0165(6) 0.0005(5) -0.0010(5) 0.0009(5) C4 0.0267(7) 0.0224(7) 0.0229(6) 0.0035(5) 0.0011(5) -0.0020(5) C5 0.0281(7) 0.0335(8) 0.0231(7) 0.0047(6) 0.0047(6) -0.0035(6) C6 0.0240(7) 0.0350(9) 0.0221(7) -0.0026(6) 0.0054(5) 0.0002(6) C7 0.0244(7) 0.0261(7) 0.0205(6) -0.0068(5) -0.0025(5) 0.0004(5) C8 0.0207(6) 0.0224(7) 0.0178(6) -0.0023(5) -0.0025(5) -0.0005(5) C9 0.0211(6) 0.0197(7) 0.0169(6) -0.0050(5) -0.0032(5) 0.0009(5) C10 0.0210(6) 0.0178(7) 0.0178(6) -0.0008(5) -0.0032(5) -0.0002(5) C11 0.0210(6) 0.0154(7) 0.0201(6) -0.0024(5) -0.0021(5) -0.0017(5) C12 0.0247(7) 0.0191(7) 0.0247(6) -0.0015(5) 0.0073(5) -0.0026(5) C13 0.0196(6) 0.0189(7) 0.0256(7) -0.0006(5) 0.0051(5) -0.0007(5) C14 0.0224(7) 0.0234(7) 0.0279(7) -0.0021(5) -0.0029(5) -0.0002(6) C15 0.0289(7) 0.0232(8) 0.0325(7) 0.0053(5) 0.0017(6) 0.0029(6) C16 0.0246(7) 0.0169(7) 0.0369(7) -0.0012(5) 0.0087(6) -0.0032(5) C17 0.0357(8) 0.0227(8) 0.0297(7) -0.0063(6) -0.0020(6) -0.0015(6) C18 0.0406(8) 0.0215(7) 0.0231(6) -0.0004(5) -0.0012(6) 0.0006(6) C19 0.0222(6) 0.0228(7) 0.0204(6) -0.0013(5) -0.0023(5) -0.0012(5) C20 0.0274(7) 0.0192(7) 0.0282(7) -0.0018(5) 0.0024(5) 0.0002(6) _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 N1 1.4424(13) . ? O1 C1 1.3409(16) . ? O2 C7 1.3372(17) . ? O2 H2 0.96(2) . ? O3 C9 1.2629(16) . ? O4 C11 1.3339(15) . ? O4 C12 1.4593(15) . ? N1 C11 1.3097(17) . ? N2 C2 1.4695(16) . ? N2 C19 1.4619(16) . ? N2 C20 1.4587(16) . ? C1 C2 1.5006(18) . ? C1 C10 1.3547(19) . ? C2 H2A 1.0000 . ? C2 C3 1.5583(17) . ? C3 H3 1.0000 . ? C3 C4 1.5298(18) . ? C3 C8 1.5231(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.5049(19) . ? C5 H5 0.9500 . ? C5 C6 1.332(2) . ? C6 H6 0.9500 . ? C6 C7 1.452(2) . ? C7 C8 1.3762(18) . ? C8 C9 1.4339(18) . ? C9 C10 1.4586(18) . ? C10 C11 1.4345(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.4982(19) . ? C13 C14 1.3821(19) . ? C13 C18 1.3913(19) . ? C14 H14 0.9500 . ? C14 C15 1.383(2) . ? C15 H15 0.9500 . ? C15 C16 1.386(2) . ? C16 H16 0.9500 . ? C16 C17 1.383(2) . ? C17 H17 0.9500 . ? C17 C18 1.385(2) . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 N1 108.37(9) . . ? C7 O2 H2 103.7(12) . . ? C11 O4 C12 114.70(10) . . ? C11 N1 O1 104.62(10) . . ? C19 N2 C2 114.30(10) . . ? C20 N2 C2 112.03(10) . . ? C20 N2 C19 111.11(10) . . ? O1 C1 C2 120.96(11) . . ? O1 C1 C10 110.87(11) . . ? C10 C1 C2 127.70(12) . . ? N2 C2 C1 112.26(10) . . ? N2 C2 H2A 107.4 . . ? N2 C2 C3 114.41(10) . . ? C1 C2 H2A 107.4 . . ? C1 C2 C3 107.62(10) . . ? C3 C2 H2A 107.4 . . ? C2 C3 H3 106.2 . . ? C4 C3 C2 111.23(10) . . ? C4 C3 H3 106.2 . . ? C8 C3 C2 116.03(10) . . ? C8 C3 H3 106.2 . . ? C8 C3 C4 110.29(11) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C5 C4 C3 110.88(12) . . ? C5 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C4 C5 H5 119.5 . . ? C6 C5 C4 120.96(13) . . ? C6 C5 H5 119.5 . . ? C5 C6 H6 120.2 . . ? C5 C6 C7 119.67(13) . . ? C7 C6 H6 120.2 . . ? O2 C7 C6 116.40(12) . . ? O2 C7 C8 122.22(13) . . ? C8 C7 C6 121.36(13) . . ? C7 C8 C3 118.09(12) . . ? C7 C8 C9 118.95(12) . . ? C9 C8 C3 122.42(11) . . ? O3 C9 C8 122.99(12) . . ? O3 C9 C10 121.43(12) . . ? C8 C9 C10 115.58(11) . . ? C1 C10 C9 121.62(12) . . ? C1 C10 C11 103.81(11) . . ? C11 C10 C9 134.34(13) . . ? O4 C11 C10 124.75(12) . . ? N1 C11 O4 122.92(12) . . ? N1 C11 C10 112.32(12) . . ? O4 C12 H12A 110.0 . . ? O4 C12 H12B 110.0 . . ? O4 C12 C13 108.68(10) . . ? H12A C12 H12B 108.3 . . ? C13 C12 H12A 110.0 . . ? C13 C12 H12B 110.0 . . ? C14 C13 C12 121.11(12) . . ? C14 C13 C18 118.54(13) . . ? C18 C13 C12 120.26(12) . . ? C13 C14 H14 119.6 . . ? C13 C14 C15 120.83(13) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 119.9 . . ? C14 C15 C16 120.27(13) . . ? C16 C15 H15 119.9 . . ? C15 C16 H16 120.3 . . ? C17 C16 C15 119.45(13) . . ? C17 C16 H16 120.3 . . ? C16 C17 H17 120.0 . . ? C16 C17 C18 119.99(13) . . ? C18 C17 H17 120.0 . . ? C13 C18 H18 119.6 . . ? C17 C18 C13 120.90(13) . . ? C17 C18 H18 119.6 . . ? N2 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? N2 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 H2 O3 0.96(2) 1.62(2) 2.5205(13) 153.7(18) . 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 N1 C11 O4 178.50(11) . . . . ? O1 N1 C11 C10 -0.99(13) . . . . ? O1 C1 C2 N2 -69.01(14) . . . . ? O1 C1 C2 C3 164.22(10) . . . . ? O1 C1 C10 C9 174.47(10) . . . . ? O1 C1 C10 C11 -0.79(13) . . . . ? O2 C7 C8 C3 175.39(11) . . . . ? O2 C7 C8 C9 3.58(18) . . . . ? O3 C9 C10 C1 -169.16(11) . . . . ? O3 C9 C10 C11 4.4(2) . . . . ? O4 C12 C13 C14 -106.43(14) . . . . ? O4 C12 C13 C18 77.16(15) . . . . ? N1 O1 C1 C2 172.96(10) . . . . ? N1 O1 C1 C10 0.23(13) . . . . ? N2 C2 C3 C4 35.12(14) . . . . ? N2 C2 C3 C8 -92.03(13) . . . . ? C1 O1 N1 C11 0.48(12) . . . . ? C1 C2 C3 C4 160.61(10) . . . . ? C1 C2 C3 C8 33.47(14) . . . . ? C1 C10 C11 O4 -178.34(11) . . . . ? C1 C10 C11 N1 1.14(14) . . . . ? C2 C1 C10 C9 2.36(19) . . . . ? C2 C1 C10 C11 -172.90(12) . . . . ? C2 C3 C4 C5 -178.80(11) . . . . ? C2 C3 C8 C7 162.65(11) . . . . ? C2 C3 C8 C9 -25.85(16) . . . . ? C3 C4 C5 C6 34.30(18) . . . . ? C3 C8 C9 O3 -178.19(11) . . . . ? C3 C8 C9 C10 2.36(16) . . . . ? C4 C3 C8 C7 35.04(14) . . . . ? C4 C3 C8 C9 -153.45(12) . . . . ? C4 C5 C6 C7 -1.7(2) . . . . ? C5 C6 C7 O2 165.97(13) . . . . ? C5 C6 C7 C8 -15.6(2) . . . . ? C6 C7 C8 C3 -3.00(17) . . . . ? C6 C7 C8 C9 -174.80(12) . . . . ? C7 C8 C9 O3 -6.75(18) . . . . ? C7 C8 C9 C10 173.80(11) . . . . ? C8 C3 C4 C5 -48.59(14) . . . . ? C8 C9 C10 C1 10.30(17) . . . . ? C8 C9 C10 C11 -176.14(13) . . . . ? C9 C10 C11 O4 7.3(2) . . . . ? C9 C10 C11 N1 -173.21(12) . . . . ? C10 C1 C2 N2 102.38(15) . . . . ? C10 C1 C2 C3 -24.39(17) . . . . ? C11 O4 C12 C13 -165.96(11) . . . . ? C12 O4 C11 N1 6.22(17) . . . . ? C12 O4 C11 C10 -174.34(11) . . . . ? C12 C13 C14 C15 -178.57(13) . . . . ? C12 C13 C18 C17 177.98(13) . . . . ? C13 C14 C15 C16 1.3(2) . . . . ? C14 C13 C18 C17 1.5(2) . . . . ? C14 C15 C16 C17 0.2(2) . . . . ? C15 C16 C17 C18 -0.9(2) . . . . ? C16 C17 C18 C13 0.0(2) . . . . ? C18 C13 C14 C15 -2.1(2) . . . . ? C19 N2 C2 C1 -44.39(14) . . . . ? C19 N2 C2 C3 78.64(13) . . . . ? C20 N2 C2 C1 83.13(13) . . . . ? C20 N2 C2 C3 -153.85(10) . . . . ?