data_04src0621 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 N2 O4, H2 O' _chemical_formula_sum 'C20 H24 N2 O5' _chemical_formula_weight 372.41 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0000 '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) _symmetry_space_group_name_hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.5936(18) _cell_length_b 7.2355(14) _cell_length_c 15.311(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.98(3) _cell_angle_gamma 90.00 _cell_volume 923.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2215 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9828 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10760 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2285 _reflns_number_gt 1991 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^ > 2\s(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^)+(0.0540P)^2^+0.3002P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2285 _refine_ls_number_parameters 255 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _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 C1 C 0.7195(3) 0.7100(4) 0.7847(2) 0.0259(7) Uani 1 1 d . . . H1A H 0.7424 0.7732 0.8430 0.039 Uiso 1 1 calc R . . H1B H 0.6136 0.6516 0.7736 0.039 Uiso 1 1 calc R . . H1C H 0.7206 0.7999 0.7370 0.039 Uiso 1 1 calc R . . C2 C 1.1108(3) 0.0719(5) 0.8251(2) 0.0282(7) Uani 1 1 d . . . H2A H 1.1461 0.0191 0.7741 0.042 Uiso 1 1 calc R . . H2B H 1.0333 -0.0115 0.8422 0.042 Uiso 1 1 calc R . . H2C H 1.2037 0.0877 0.8762 0.042 Uiso 1 1 calc R . . C3 C 0.9671(3) 0.5565(4) 0.85669(19) 0.0217(6) Uani 1 1 d . . . C4 C 1.0938(3) 0.4125(4) 0.85703(19) 0.0209(6) Uani 1 1 d . . . H4 H 1.1307 0.3656 0.9201 0.025 Uiso 1 1 calc R . . C5 C 0.9023(3) 0.2572(4) 0.73218(19) 0.0222(6) Uani 1 1 d . . . C6 C 0.8083(3) 0.4355(4) 0.71133(19) 0.0203(6) Uani 1 1 d . . . H6 H 0.6933 0.3998 0.7033 0.024 Uiso 1 1 calc R . . C7 C 1.2390(3) 0.5105(4) 0.8329(2) 0.0236(6) Uani 1 1 d . . . H7A H 1.2111 0.5371 0.7676 0.028 Uiso 1 1 calc R . . H7B H 1.2562 0.6305 0.8649 0.028 Uiso 1 1 calc R . . C8 C 1.3942(3) 0.4045(4) 0.85542(19) 0.0213(6) Uani 1 1 d . . . C9 C 1.5078(3) 0.4363(4) 0.9366(2) 0.0246(6) Uani 1 1 d . . . H9 H 1.4865 0.5255 0.9777 0.029 Uiso 1 1 calc R . . C10 C 1.6515(3) 0.3382(4) 0.9575(2) 0.0239(6) Uani 1 1 d . . . H10 H 1.7285 0.3633 1.0121 0.029 Uiso 1 1 calc R . . C11 C 1.6830(3) 0.2043(4) 0.89942(19) 0.0227(6) Uani 1 1 d . . . C12 C 1.5710(3) 0.1720(5) 0.81825(19) 0.0245(6) Uani 1 1 d . . . H12 H 1.5912 0.0806 0.7778 0.029 Uiso 1 1 calc R . . C13 C 1.4303(3) 0.2736(4) 0.79681(19) 0.0239(6) Uani 1 1 d . . . H13 H 1.3565 0.2533 0.7405 0.029 Uiso 1 1 calc R . . C14 C 0.8202(3) 0.5168(5) 0.61958(19) 0.0226(6) Uani 1 1 d . . . H14A H 0.7745 0.4257 0.5720 0.027 Uiso 1 1 calc R . . H14B H 0.7523 0.6289 0.6077 0.027 Uiso 1 1 calc R . . C15 C 0.9863(3) 0.5673(4) 0.61109(18) 0.0213(6) Uani 1 1 d . . . C16 C 1.0428(3) 0.7470(5) 0.62450(19) 0.0228(6) Uani 1 1 d . . . H16 H 0.9763 0.8395 0.6405 0.027 Uiso 1 1 calc R . . C17 C 1.1952(3) 0.7956(5) 0.6151(2) 0.0239(6) Uani 1 1 d . . . H17 H 1.2320 0.9194 0.6249 0.029 Uiso 1 1 calc R . . C18 C 1.2924(3) 0.6608(5) 0.59116(19) 0.0230(6) Uani 1 1 d . . . C19 C 1.2378(3) 0.4789(4) 0.5777(2) 0.0237(7) Uani 1 1 d . . . H19 H 1.3045 0.3865 0.5618 0.028 Uiso 1 1 calc R . . C20 C 1.0872(3) 0.4331(4) 0.58762(19) 0.0235(6) Uani 1 1 d . . . H20 H 1.0511 0.3089 0.5784 0.028 Uiso 1 1 calc R . . N1 N 0.8415(2) 0.5686(3) 0.78538(15) 0.0206(5) Uani 1 1 d . . . N2 N 1.0349(3) 0.2528(3) 0.79917(16) 0.0220(5) Uani 1 1 d . . . O1 O 0.9863(2) 0.6662(3) 0.92115(14) 0.0266(5) Uani 1 1 d . . . O2 O 0.8526(2) 0.1184(3) 0.68626(14) 0.0268(5) Uani 1 1 d . . . O3 O 1.8192(2) 0.1010(3) 0.91797(14) 0.0296(5) Uani 1 1 d . . . H3 H 1.8716 0.1225 0.9708 0.044 Uiso 1 1 calc R . . O4 O 1.4422(2) 0.6997(3) 0.57784(15) 0.0274(5) Uani 1 1 d . . . H4A H 1.4627 0.8123 0.5878 0.041 Uiso 1 1 calc R . . O21 O 1.4609(2) 0.5504(3) 0.40975(15) 0.0304(5) Uani 1 1 d D . . H21 H 1.470(4) 0.577(6) 0.4637(13) 0.046 Uiso 1 1 d D . . H22 H 1.365(3) 0.572(6) 0.3822(19) 0.046 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0214(13) 0.0233(17) 0.0322(16) -0.0022(13) 0.0050(11) 0.0038(13) C2 0.0246(14) 0.0169(15) 0.0419(18) 0.0037(14) 0.0059(12) 0.0021(12) C3 0.0196(13) 0.0199(16) 0.0253(14) -0.0003(12) 0.0052(10) -0.0028(12) C4 0.0200(13) 0.0155(14) 0.0269(14) 0.0000(12) 0.0048(10) -0.0014(12) C5 0.0194(13) 0.0193(15) 0.0286(15) 0.0003(12) 0.0073(10) -0.0012(12) C6 0.0177(12) 0.0168(14) 0.0259(14) -0.0034(12) 0.0045(10) 0.0002(12) C7 0.0197(13) 0.0191(15) 0.0311(16) 0.0013(13) 0.0044(11) -0.0007(12) C8 0.0167(12) 0.0187(15) 0.0284(15) 0.0035(12) 0.0051(10) -0.0004(11) C9 0.0229(14) 0.0201(16) 0.0301(16) -0.0023(13) 0.0055(11) 0.0014(13) C10 0.0199(13) 0.0228(16) 0.0271(15) 0.0015(12) 0.0020(11) 0.0026(12) C11 0.0219(13) 0.0190(16) 0.0284(15) 0.0020(12) 0.0083(11) 0.0021(12) C12 0.0237(14) 0.0245(16) 0.0260(15) -0.0011(13) 0.0076(11) 0.0023(13) C13 0.0224(13) 0.0243(16) 0.0240(15) 0.0011(12) 0.0036(10) -0.0002(13) C14 0.0189(12) 0.0221(15) 0.0250(14) 0.0004(12) 0.0016(10) 0.0006(12) C15 0.0210(13) 0.0230(16) 0.0195(13) 0.0004(12) 0.0041(10) 0.0026(12) C16 0.0200(13) 0.0229(16) 0.0258(15) 0.0009(12) 0.0062(10) 0.0066(12) C17 0.0243(14) 0.0190(15) 0.0283(15) 0.0011(12) 0.0062(11) 0.0002(12) C18 0.0194(13) 0.0281(17) 0.0214(14) 0.0025(12) 0.0044(10) -0.0006(12) C19 0.0225(14) 0.0216(17) 0.0278(16) -0.0032(12) 0.0074(11) 0.0029(12) C20 0.0252(14) 0.0192(15) 0.0257(15) -0.0024(12) 0.0054(11) -0.0018(13) N1 0.0171(11) 0.0169(12) 0.0269(12) 0.0004(10) 0.0037(9) 0.0009(10) N2 0.0212(11) 0.0129(12) 0.0308(14) -0.0015(10) 0.0041(9) 0.0010(10) O1 0.0231(10) 0.0245(12) 0.0305(11) -0.0058(10) 0.0032(8) 0.0026(9) O2 0.0254(10) 0.0186(12) 0.0362(12) -0.0061(9) 0.0070(8) -0.0009(9) O3 0.0229(10) 0.0329(14) 0.0311(11) 0.0002(10) 0.0030(8) 0.0106(10) O4 0.0204(10) 0.0274(13) 0.0354(12) -0.0050(10) 0.0089(8) -0.0032(9) O21 0.0263(11) 0.0343(14) 0.0300(11) -0.0011(10) 0.0058(9) 0.0089(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.464(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N2 1.474(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 O1 1.246(4) . ? C3 N1 1.340(3) . ? C3 C4 1.507(4) . ? C4 N2 1.469(4) . ? C4 C7 1.555(4) . ? C4 H4 1.0000 . ? C5 O2 1.241(4) . ? C5 N2 1.337(4) . ? C5 C6 1.515(4) . ? C6 N1 1.462(4) . ? C6 C14 1.549(4) . ? C6 H6 1.0000 . ? C7 C8 1.504(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C13 1.390(4) . ? C8 C9 1.401(4) . ? C9 C10 1.393(4) . ? C9 H9 0.9500 . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 O3 1.360(3) . ? C11 C12 1.396(4) . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.509(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.386(5) . ? C15 C20 1.405(4) . ? C16 C17 1.397(4) . ? C16 H16 0.9500 . ? C17 C18 1.389(4) . ? C17 H17 0.9500 . ? C18 O4 1.380(3) . ? C18 C19 1.396(4) . ? C19 C20 1.380(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? O3 H3 0.8400 . ? O4 H4A 0.8400 . ? O21 H21 0.833(18) . ? O21 H22 0.847(18) . ? 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 N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C3 N1 122.0(3) . . ? O1 C3 C4 118.7(2) . . ? N1 C3 C4 119.2(3) . . ? N2 C4 C3 113.5(2) . . ? N2 C4 C7 113.3(2) . . ? C3 C4 C7 107.7(2) . . ? N2 C4 H4 107.4 . . ? C3 C4 H4 107.4 . . ? C7 C4 H4 107.4 . . ? O2 C5 N2 121.9(3) . . ? O2 C5 C6 118.5(2) . . ? N2 C5 C6 119.6(3) . . ? N1 C6 C5 113.8(2) . . ? N1 C6 C14 114.2(3) . . ? C5 C6 C14 111.5(2) . . ? N1 C6 H6 105.5 . . ? C5 C6 H6 105.5 . . ? C14 C6 H6 105.5 . . ? C8 C7 C4 115.5(3) . . ? C8 C7 H7A 108.4 . . ? C4 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? C4 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C13 C8 C9 117.9(3) . . ? C13 C8 C7 121.6(3) . . ? C9 C8 C7 120.5(3) . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? O3 C11 C10 122.8(2) . . ? O3 C11 C12 117.9(3) . . ? C10 C11 C12 119.3(3) . . ? C13 C12 C11 119.8(3) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C8 121.8(3) . . ? C12 C13 H13 119.1 . . ? C8 C13 H13 119.1 . . ? C15 C14 C6 116.2(2) . . ? C15 C14 H14A 108.2 . . ? C6 C14 H14A 108.2 . . ? C15 C14 H14B 108.2 . . ? C6 C14 H14B 108.2 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C20 118.1(3) . . ? C16 C15 C14 121.3(3) . . ? C20 C15 C14 120.6(3) . . ? C15 C16 C17 121.6(3) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 119.3(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? O4 C18 C17 122.5(3) . . ? O4 C18 C19 117.6(3) . . ? C17 C18 C19 119.9(3) . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C15 121.0(3) . . ? C19 C20 H20 119.5 . . ? C15 C20 H20 119.5 . . ? C3 N1 C6 123.8(2) . . ? C3 N1 C1 119.1(2) . . ? C6 N1 C1 116.7(2) . . ? C5 N2 C4 123.4(2) . . ? C5 N2 C2 117.9(2) . . ? C4 N2 C2 118.0(2) . . ? C11 O3 H3 109.5 . . ? C18 O4 H4A 109.5 . . ? H21 O21 H22 107(3) . . ? 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 O3 H3 O1 0.84 1.83 2.664(3) 171.0 2_847 O4 H4A O21 0.84 1.84 2.663(3) 165.9 2_856 O21 H21 O4 0.833(18) 2.03(2) 2.831(3) 162(4) . O21 H22 O2 0.847(18) 1.937(18) 2.783(3) 177(3) 2_756 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.244 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.050