# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_3a _database_code_depnum_ccdc_archive 'CCDC 858579' #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1323786906.cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 N4 O4' _chemical_formula_sum 'C22 H24 N4 O4' _chemical_formula_weight 408.45 _chemical_absolute_configuration syn 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.4632(17) _cell_length_b 11.4185(19) _cell_length_c 16.753(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2001.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5280 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 28.02 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9711 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10141 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3525 _reflns_number_gt 3416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0392P)^2^+0.4224P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(10) _refine_ls_number_reflns 3525 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0800 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 0.12986(14) 0.21102(12) 0.16474(9) 0.0349(3) Uani 1 1 d . . . O2 O 0.45263(12) 0.60389(11) 0.02354(7) 0.0242(3) Uani 1 1 d . . . O3 O 0.13512(13) 0.59589(11) 0.03280(7) 0.0247(3) Uani 1 1 d . . . O4 O 0.15031(15) 0.53794(12) -0.20952(8) 0.0354(4) Uani 1 1 d . . . N1 N 0.21901(16) 0.37055(14) 0.10515(9) 0.0245(4) Uani 1 1 d . . . N2 N 0.36368(15) 0.58250(13) 0.14631(9) 0.0210(3) Uani 1 1 d . . . N3 N 0.22015(14) 0.73725(12) -0.04514(8) 0.0199(3) Uani 1 1 d . . . N4 N 0.31655(17) 0.54005(15) -0.12430(10) 0.0291(4) Uani 1 1 d . . . C1 C 0.1210(2) 0.31058(17) 0.13978(11) 0.0257(4) Uani 1 1 d . . . C2 C 0.34456(19) 0.32976(16) 0.09172(11) 0.0234(4) Uani 1 1 d . . . C3 C 0.44194(19) 0.41114(16) 0.07746(10) 0.0222(4) Uani 1 1 d . . . C4 C 0.5643(2) 0.37231(18) 0.05849(11) 0.0269(4) Uani 1 1 d . . . C5 C 0.5929(2) 0.25390(19) 0.05691(12) 0.0308(5) Uani 1 1 d . . . C6 C 0.4970(2) 0.17366(19) 0.07125(12) 0.0339(5) Uani 1 1 d . . . C7 C 0.3736(2) 0.20935(17) 0.08715(11) 0.0289(4) Uani 1 1 d . . . C8 C 0.41959(17) 0.54118(16) 0.07952(10) 0.0202(4) Uani 1 1 d . . . C9 C 0.32187(17) 0.69998(15) 0.15541(10) 0.0207(4) Uani 1 1 d . . . C10 C 0.24308(17) 0.75307(16) 0.09872(10) 0.0211(4) Uani 1 1 d . . . C11 C 0.1991(2) 0.86684(16) 0.11238(11) 0.0235(4) Uani 1 1 d . . . C12 C 0.2338(2) 0.92753(17) 0.18092(11) 0.0266(4) Uani 1 1 d . . . C13 C 0.3136(2) 0.87427(17) 0.23597(11) 0.0260(4) Uani 1 1 d . . . C14 C 0.35663(19) 0.76130(16) 0.22394(10) 0.0239(4) Uani 1 1 d . . . C15 C 0.19560(17) 0.68796(15) 0.02636(10) 0.0194(4) Uani 1 1 d . . . C16 C 0.15717(19) 0.69684(16) -0.11820(11) 0.0222(4) Uani 1 1 d . . . C17 C 0.1825(2) 0.79801(17) -0.17644(11) 0.0261(4) Uani 1 1 d . . . C18 C 0.3144(2) 0.84051(18) -0.15108(12) 0.0296(5) Uani 1 1 d . . . C19 C 0.3089(2) 0.83646(17) -0.06043(11) 0.0256(4) Uani 1 1 d . . . C20 C 0.20863(19) 0.58312(16) -0.15363(11) 0.0251(4) Uani 1 1 d . . . C21 C 0.3751(3) 0.4345(2) -0.15619(16) 0.0394(5) Uani 1 1 d . . . C22 C -0.0012(2) 0.3780(2) 0.14508(16) 0.0365(5) Uani 1 1 d . . . H1N H 0.201(2) 0.445(2) 0.0933(12) 0.029(5) Uiso 1 1 d . . . H2N H 0.350(2) 0.5365(19) 0.1867(14) 0.036(6) Uiso 1 1 d . . . H4N H 0.355(2) 0.572(2) -0.0848(13) 0.035(6) Uiso 1 1 d . . . H4 H 0.628(2) 0.4309(18) 0.0458(12) 0.028(5) Uiso 1 1 d . . . H5 H 0.675(2) 0.2267(17) 0.0477(11) 0.023(5) Uiso 1 1 d . . . H6 H 0.507(2) 0.094(2) 0.0686(13) 0.034(6) Uiso 1 1 d . . . H7 H 0.310(2) 0.1547(17) 0.0885(11) 0.019(5) Uiso 1 1 d . . . H11 H 0.1455(18) 0.8997(15) 0.0772(10) 0.010(4) Uiso 1 1 d . . . H12 H 0.197(2) 1.0058(18) 0.1883(11) 0.024(5) Uiso 1 1 d . . . H13 H 0.340(2) 0.9138(19) 0.2801(14) 0.034(6) Uiso 1 1 d . . . H14 H 0.4112(18) 0.7257(16) 0.2605(11) 0.013(4) Uiso 1 1 d . . . H16 H 0.066(2) 0.6854(16) -0.1064(11) 0.019(5) Uiso 1 1 d . . . H17A H 0.118(2) 0.8582(17) -0.1668(12) 0.023(5) Uiso 1 1 d . . . H17B H 0.178(2) 0.7722(18) -0.2311(13) 0.032(6) Uiso 1 1 d . . . H18A H 0.332(2) 0.9171(18) -0.1699(11) 0.024(5) Uiso 1 1 d . . . H18B H 0.384(2) 0.7854(18) -0.1698(12) 0.024(5) Uiso 1 1 d . . . H19A H 0.390(2) 0.8236(16) -0.0372(12) 0.017(5) Uiso 1 1 d . . . H19B H 0.2712(17) 0.9104(16) -0.0394(10) 0.013(4) Uiso 1 1 d . . . H21A H 0.406(3) 0.448(2) -0.2102(18) 0.059(8) Uiso 1 1 d . . . H21B H 0.315(3) 0.375(2) -0.1569(15) 0.054(8) Uiso 1 1 d . . . H21C H 0.448(3) 0.413(2) -0.1264(17) 0.060(8) Uiso 1 1 d . . . H22A H 0.004(3) 0.451(3) 0.1260(18) 0.071(9) Uiso 1 1 d . . . H22B H -0.070(3) 0.339(3) 0.1073(18) 0.068(9) Uiso 1 1 d . . . H22C H -0.031(3) 0.373(2) 0.1971(17) 0.051(7) 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 0.0360(8) 0.0276(7) 0.0410(8) 0.0092(6) -0.0023(7) -0.0068(6) O2 0.0231(7) 0.0271(7) 0.0223(7) 0.0035(6) 0.0019(6) 0.0000(6) O3 0.0276(7) 0.0216(6) 0.0248(7) 0.0011(5) -0.0010(6) -0.0034(6) O4 0.0378(9) 0.0393(8) 0.0290(7) -0.0149(6) -0.0066(7) 0.0022(7) N1 0.0255(9) 0.0187(8) 0.0292(9) 0.0009(7) 0.0006(7) 0.0000(7) N2 0.0250(8) 0.0216(8) 0.0164(7) 0.0029(6) -0.0016(7) 0.0000(7) N3 0.0222(8) 0.0199(7) 0.0177(7) -0.0014(6) -0.0011(6) -0.0009(6) N4 0.0292(9) 0.0300(9) 0.0283(9) -0.0102(7) -0.0030(8) 0.0039(8) C1 0.0301(10) 0.0244(10) 0.0227(9) -0.0009(8) -0.0008(8) -0.0050(8) C2 0.0278(10) 0.0248(9) 0.0176(9) -0.0005(7) -0.0022(8) 0.0015(8) C3 0.0270(10) 0.0256(10) 0.0141(8) 0.0003(7) -0.0024(7) 0.0033(8) C4 0.0276(11) 0.0335(11) 0.0196(9) 0.0005(8) -0.0005(8) 0.0034(9) C5 0.0298(12) 0.0405(12) 0.0223(10) -0.0049(9) 0.0005(8) 0.0125(10) C6 0.0480(14) 0.0275(11) 0.0261(11) -0.0017(8) 0.0009(10) 0.0128(10) C7 0.0358(12) 0.0252(10) 0.0256(10) -0.0002(8) 0.0007(9) 0.0008(9) C8 0.0162(9) 0.0250(10) 0.0193(9) 0.0016(7) -0.0019(7) -0.0024(8) C9 0.0215(9) 0.0203(9) 0.0202(9) 0.0037(7) 0.0052(8) -0.0028(7) C10 0.0228(9) 0.0243(9) 0.0164(8) 0.0029(8) 0.0024(7) -0.0028(8) C11 0.0272(11) 0.0246(9) 0.0187(9) 0.0030(8) -0.0006(9) 0.0041(8) C12 0.0349(11) 0.0212(10) 0.0238(10) -0.0006(8) 0.0040(8) 0.0022(8) C13 0.0327(11) 0.0283(10) 0.0172(9) -0.0063(8) 0.0001(8) -0.0025(9) C14 0.0245(10) 0.0307(10) 0.0164(9) 0.0042(8) -0.0020(8) -0.0021(8) C15 0.0185(9) 0.0209(8) 0.0187(9) 0.0015(7) -0.0033(7) 0.0043(8) C16 0.0206(10) 0.0280(9) 0.0179(8) -0.0019(7) -0.0021(7) 0.0012(8) C17 0.0296(11) 0.0299(10) 0.0187(9) 0.0010(8) 0.0012(8) 0.0027(9) C18 0.0344(12) 0.0300(11) 0.0242(10) 0.0047(8) 0.0003(9) -0.0059(9) C19 0.0297(12) 0.0239(10) 0.0232(10) 0.0023(7) -0.0007(9) -0.0038(9) C20 0.0270(10) 0.0261(9) 0.0221(9) -0.0024(8) -0.0006(9) -0.0018(8) C21 0.0399(14) 0.0328(12) 0.0454(14) -0.0104(10) 0.0060(12) 0.0088(11) C22 0.0325(12) 0.0315(12) 0.0454(14) 0.0049(11) 0.0130(11) -0.0036(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 O1 C1 1.215(2) . ? O2 C8 1.230(2) . ? O3 C15 1.232(2) . ? O4 C20 1.231(2) . ? N1 C1 1.363(3) . ? N1 C2 1.412(3) . ? N2 C8 1.348(2) . ? N2 C9 1.419(2) . ? N3 C15 1.348(2) . ? N3 C16 1.465(2) . ? N3 C19 1.487(2) . ? N4 C20 1.326(3) . ? N4 C21 1.454(3) . ? C1 C22 1.495(3) . ? C2 C3 1.400(3) . ? C2 C7 1.410(3) . ? C3 C4 1.392(3) . ? C3 C8 1.504(3) . ? C4 C5 1.385(3) . ? C5 C6 1.380(3) . ? C6 C7 1.379(3) . ? C9 C14 1.393(3) . ? C9 C10 1.396(3) . ? C10 C11 1.397(3) . ? C10 C15 1.506(2) . ? C11 C12 1.389(3) . ? C12 C13 1.385(3) . ? C13 C14 1.381(3) . ? C16 C20 1.526(3) . ? C16 C17 1.535(3) . ? C17 C18 1.523(3) . ? C18 C19 1.520(3) . ? 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 C2 127.03(17) . . ? C8 N2 C9 123.64(15) . . ? C15 N3 C16 121.68(15) . . ? C15 N3 C19 126.17(14) . . ? C16 N3 C19 112.14(14) . . ? C20 N4 C21 122.01(19) . . ? O1 C1 N1 124.00(19) . . ? O1 C1 C22 121.79(19) . . ? N1 C1 C22 114.21(17) . . ? C3 C2 C7 118.75(18) . . ? C3 C2 N1 119.05(16) . . ? C7 C2 N1 122.07(18) . . ? C4 C3 C2 119.82(17) . . ? C4 C3 C8 117.57(17) . . ? C2 C3 C8 122.58(17) . . ? C5 C4 C3 120.9(2) . . ? C6 C5 C4 119.2(2) . . ? C7 C6 C5 121.2(2) . . ? C6 C7 C2 120.0(2) . . ? O2 C8 N2 123.46(16) . . ? O2 C8 C3 120.92(16) . . ? N2 C8 C3 115.61(15) . . ? C14 C9 C10 119.78(17) . . ? C14 C9 N2 118.90(16) . . ? C10 C9 N2 121.28(16) . . ? C9 C10 C11 119.14(17) . . ? C9 C10 C15 121.87(16) . . ? C11 C10 C15 118.82(16) . . ? C12 C11 C10 120.86(18) . . ? C13 C12 C11 119.28(18) . . ? C14 C13 C12 120.64(18) . . ? C13 C14 C9 120.30(18) . . ? O3 C15 N3 122.15(16) . . ? O3 C15 C10 121.34(15) . . ? N3 C15 C10 116.50(15) . . ? N3 C16 C20 115.74(15) . . ? N3 C16 C17 102.50(15) . . ? C20 C16 C17 109.41(15) . . ? C18 C17 C16 102.64(15) . . ? C19 C18 C17 103.56(17) . . ? N3 C19 C18 102.65(16) . . ? O4 C20 N4 123.27(18) . . ? O4 C20 C16 118.52(18) . . ? N4 C20 C16 118.17(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 0.4(3) . . . . ? C2 N1 C1 C22 -179.71(18) . . . . ? C1 N1 C2 C3 -161.47(17) . . . . ? C1 N1 C2 C7 22.7(3) . . . . ? C7 C2 C3 C4 0.6(3) . . . . ? N1 C2 C3 C4 -175.43(16) . . . . ? C7 C2 C3 C8 178.87(16) . . . . ? N1 C2 C3 C8 2.9(3) . . . . ? C2 C3 C4 C5 -2.9(3) . . . . ? C8 C3 C4 C5 178.75(17) . . . . ? C3 C4 C5 C6 2.6(3) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C2 -2.2(3) . . . . ? C3 C2 C7 C6 1.9(3) . . . . ? N1 C2 C7 C6 177.80(18) . . . . ? C9 N2 C8 O2 8.4(3) . . . . ? C9 N2 C8 C3 -172.55(17) . . . . ? C4 C3 C8 O2 50.4(2) . . . . ? C2 C3 C8 O2 -127.98(19) . . . . ? C4 C3 C8 N2 -128.74(17) . . . . ? C2 C3 C8 N2 52.9(2) . . . . ? C8 N2 C9 C14 -131.09(18) . . . . ? C8 N2 C9 C10 51.4(3) . . . . ? C14 C9 C10 C11 -0.8(3) . . . . ? N2 C9 C10 C11 176.71(17) . . . . ? C14 C9 C10 C15 -175.86(16) . . . . ? N2 C9 C10 C15 1.6(3) . . . . ? C9 C10 C11 C12 0.7(3) . . . . ? C15 C10 C11 C12 175.89(17) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C14 -1.2(3) . . . . ? C12 C13 C14 C9 1.0(3) . . . . ? C10 C9 C14 C13 -0.1(3) . . . . ? N2 C9 C14 C13 -177.61(17) . . . . ? C16 N3 C15 O3 11.4(3) . . . . ? C19 N3 C15 O3 -169.50(17) . . . . ? C16 N3 C15 C10 -167.00(15) . . . . ? C19 N3 C15 C10 12.1(3) . . . . ? C9 C10 C15 O3 56.4(2) . . . . ? C11 C10 C15 O3 -118.7(2) . . . . ? C9 C10 C15 N3 -125.15(18) . . . . ? C11 C10 C15 N3 59.8(2) . . . . ? C15 N3 C16 C20 -77.1(2) . . . . ? C19 N3 C16 C20 103.68(18) . . . . ? C15 N3 C16 C17 163.87(16) . . . . ? C19 N3 C16 C17 -15.31(19) . . . . ? N3 C16 C17 C18 34.15(19) . . . . ? C20 C16 C17 C18 -89.20(19) . . . . ? C16 C17 C18 C19 -41.0(2) . . . . ? C15 N3 C19 C18 171.06(17) . . . . ? C16 N3 C19 C18 -9.8(2) . . . . ? C17 C18 C19 N3 31.2(2) . . . . ? C21 N4 C20 O4 -0.1(3) . . . . ? C21 N4 C20 C16 -177.80(19) . . . . ? N3 C16 C20 O4 171.79(17) . . . . ? C17 C16 C20 O4 -73.1(2) . . . . ? N3 C16 C20 N4 -10.4(2) . . . . ? C17 C16 C20 N4 104.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.90(2) 2.11(2) 2.977(2) 161.8(18) . N4 H4N O2 0.85(2) 2.12(2) 2.948(2) 165(2) . N2 H2N O4 0.87(2) 1.94(2) 2.783(2) 165(2) 2_565 C12 H12 O1 0.98(2) 2.48(2) 3.426(2) 162.4(16) 1_565 C11 H11 O2 0.896(19) 2.631(19) 3.456(2) 153.5(15) 4_465 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.196 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.037 data_3b _database_code_depnum_ccdc_archive 'CCDC 858580' #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1323786906.cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 N4 O4' _chemical_formula_sum 'C22 H24 N4 O4' _chemical_formula_weight 408.45 _chemical_absolute_configuration syn 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.4654(8) _cell_length_b 11.4224(9) _cell_length_c 16.7268(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1999.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6904 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.26 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details 'Bruker SADABS' _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_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14600 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3518 _reflns_number_gt 3459 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0298P)^2^+0.5114P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(9) _refine_ls_number_reflns 3518 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0704 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 O1 O 0.62975(12) -0.28898(10) 0.83567(8) 0.0248(3) Uani 1 1 d . . . O2 O 0.95214(11) 0.10492(10) 0.97721(7) 0.0189(3) Uani 1 1 d . . . O3 O 0.63445(11) 0.09636(10) 0.96748(7) 0.0193(3) Uani 1 1 d . . . O4 O 0.64876(13) 0.03847(11) 1.21033(7) 0.0263(3) Uani 1 1 d . . . N1 N 0.71879(14) -0.12891(13) 0.89543(8) 0.0188(3) Uani 1 1 d . . . N2 N 0.86347(14) 0.08338(12) 0.85368(8) 0.0164(3) Uani 1 1 d . . . N3 N 0.71974(13) 0.23769(12) 1.04560(8) 0.0156(3) Uani 1 1 d . . . N4 N 0.81584(15) 0.04073(13) 1.12531(9) 0.0221(3) Uani 1 1 d . . . C1 C 0.62060(17) -0.18953(15) 0.86106(10) 0.0190(4) Uani 1 1 d . . . C2 C 0.84467(16) -0.16970(15) 0.90861(10) 0.0178(4) Uani 1 1 d . . . C3 C 0.94196(17) -0.08783(15) 0.92278(9) 0.0173(4) Uani 1 1 d . . . C4 C 1.06481(17) -0.12671(16) 0.94146(10) 0.0198(4) Uani 1 1 d . . . C5 C 1.09361(18) -0.24453(17) 0.94327(11) 0.0236(4) Uani 1 1 d . . . C6 C 0.99737(19) -0.32564(17) 0.92866(11) 0.0246(4) Uani 1 1 d . . . C7 C 0.87399(19) -0.28946(15) 0.91287(10) 0.0211(4) Uani 1 1 d . . . C8 C 0.91930(15) 0.04207(15) 0.92077(10) 0.0163(4) Uani 1 1 d . . . C9 C 0.82132(15) 0.20073(14) 0.84457(10) 0.0157(3) Uani 1 1 d . . . C10 C 0.74264(15) 0.25414(15) 0.90162(9) 0.0170(4) Uani 1 1 d . . . C11 C 0.69837(17) 0.36729(15) 0.88799(10) 0.0182(4) Uani 1 1 d . . . C12 C 0.73295(17) 0.42847(16) 0.81940(10) 0.0206(4) Uani 1 1 d . . . C13 C 0.81306(18) 0.37541(15) 0.76410(10) 0.0204(4) Uani 1 1 d . . . C14 C 0.85644(16) 0.26219(15) 0.77586(10) 0.0185(4) Uani 1 1 d . . . C15 C 0.69558(15) 0.18882(14) 0.97388(9) 0.0157(3) Uani 1 1 d . . . C16 C 0.65616(16) 0.19728(15) 1.11888(10) 0.0172(4) Uani 1 1 d . . . C17 C 0.68180(17) 0.29831(16) 1.17726(10) 0.0199(4) Uani 1 1 d . . . C18 C 0.81415(18) 0.34089(16) 1.15194(11) 0.0223(4) Uani 1 1 d . . . C19 C 0.80845(18) 0.33661(15) 1.06087(10) 0.0189(4) Uani 1 1 d . . . C20 C 0.70784(17) 0.08351(15) 1.15417(10) 0.0192(4) Uani 1 1 d . . . C21 C 0.8743(2) -0.06484(18) 1.15754(13) 0.0291(4) Uani 1 1 d . . . C22 C 0.49726(19) -0.12212(18) 0.85663(13) 0.0265(4) Uani 1 1 d . . . H1N H 0.7022(18) -0.0559(19) 0.9084(11) 0.021(5) Uiso 1 1 d . . . H2N H 0.852(2) 0.0355(17) 0.8137(12) 0.026(5) Uiso 1 1 d . . . H4N H 0.851(2) 0.0727(17) 1.0850(12) 0.023(5) Uiso 1 1 d . . . H4 H 1.1275(18) -0.0696(16) 0.9541(10) 0.017(4) Uiso 1 1 d . . . H5 H 1.1804(18) -0.2709(15) 0.9537(10) 0.015(4) Uiso 1 1 d . . . H6 H 1.0129(18) -0.4081(19) 0.9307(12) 0.025(5) Uiso 1 1 d . . . H7 H 0.8083(18) -0.3447(16) 0.9056(10) 0.018(5) Uiso 1 1 d . . . H11 H 0.6437(17) 0.4009(14) 0.9247(10) 0.009(4) Uiso 1 1 d . . . H12 H 0.6985(18) 0.5080(17) 0.8122(11) 0.020(5) Uiso 1 1 d . . . H13 H 0.839(2) 0.4165(18) 0.7172(12) 0.028(5) Uiso 1 1 d . . . H14 H 0.9112(17) 0.2244(16) 0.7381(10) 0.013(4) Uiso 1 1 d . . . H16 H 0.5666(18) 0.1861(15) 1.1068(10) 0.014(4) Uiso 1 1 d . . . H17A H 0.6758(19) 0.2717(17) 1.2347(12) 0.025(5) Uiso 1 1 d . . . H17B H 0.6173(18) 0.3611(16) 1.1683(11) 0.017(5) Uiso 1 1 d . . . H18A H 0.8801(18) 0.2860(16) 1.1704(11) 0.015(4) Uiso 1 1 d . . . H18B H 0.8309(17) 0.4210(16) 1.1714(10) 0.012(4) Uiso 1 1 d . . . H19A H 0.8903(18) 0.3237(16) 1.0359(11) 0.015(4) Uiso 1 1 d . . . H19B H 0.7734(16) 0.4087(16) 1.0397(10) 0.011(4) Uiso 1 1 d . . . H21A H 0.813(2) -0.1288(19) 1.1589(12) 0.030(5) Uiso 1 1 d . . . H21B H 0.945(3) -0.090(2) 1.1260(15) 0.050(7) Uiso 1 1 d . . . H21C H 0.906(2) -0.053(2) 1.2119(15) 0.044(7) Uiso 1 1 d . . . H22A H 0.432(2) -0.165(2) 0.8923(14) 0.044(6) Uiso 1 1 d . . . H22B H 0.507(2) -0.045(2) 0.8778(16) 0.058(8) Uiso 1 1 d . . . H23C H 0.468(2) -0.127(2) 0.8040(15) 0.041(6) 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 0.0263(6) 0.0207(7) 0.0273(7) -0.0060(5) 0.0012(6) -0.0044(5) O2 0.0184(6) 0.0215(6) 0.0168(6) -0.0029(5) -0.0012(5) -0.0002(5) O3 0.0213(6) 0.0183(6) 0.0184(6) -0.0008(5) 0.0010(5) -0.0019(5) O4 0.0284(7) 0.0296(7) 0.0210(6) 0.0100(5) 0.0054(6) 0.0009(6) N1 0.0211(8) 0.0145(8) 0.0209(8) -0.0009(6) -0.0007(6) 0.0004(6) N2 0.0196(7) 0.0161(7) 0.0134(7) -0.0027(6) -0.0003(6) -0.0008(6) N3 0.0183(7) 0.0143(7) 0.0142(7) 0.0021(6) 0.0016(6) 0.0001(6) N4 0.0225(8) 0.0237(8) 0.0200(8) 0.0074(6) 0.0027(6) 0.0030(7) C1 0.0220(9) 0.0198(9) 0.0151(8) 0.0016(7) 0.0013(7) -0.0037(7) C2 0.0204(9) 0.0210(9) 0.0119(8) -0.0003(6) 0.0008(7) 0.0012(7) C3 0.0209(9) 0.0208(9) 0.0104(8) 0.0004(7) 0.0018(7) 0.0012(7) C4 0.0217(9) 0.0236(9) 0.0141(8) 0.0001(7) 0.0005(7) -0.0009(8) C5 0.0237(10) 0.0320(11) 0.0150(8) 0.0036(8) 0.0002(7) 0.0074(8) C6 0.0351(11) 0.0201(10) 0.0187(9) 0.0016(7) 0.0000(8) 0.0087(8) C7 0.0267(9) 0.0197(9) 0.0171(9) -0.0005(7) -0.0015(8) -0.0025(8) C8 0.0129(8) 0.0208(9) 0.0153(8) -0.0006(7) 0.0019(6) -0.0028(7) C9 0.0156(8) 0.0166(8) 0.0149(8) -0.0027(7) -0.0033(7) -0.0015(7) C10 0.0172(8) 0.0206(9) 0.0131(8) -0.0015(7) -0.0026(7) -0.0033(7) C11 0.0201(9) 0.0204(9) 0.0141(8) -0.0023(7) -0.0015(7) 0.0026(7) C12 0.0244(9) 0.0183(9) 0.0189(9) 0.0003(7) -0.0040(7) 0.0004(7) C13 0.0263(9) 0.0217(9) 0.0131(8) 0.0035(7) -0.0007(8) -0.0030(8) C14 0.0182(8) 0.0232(9) 0.0141(8) -0.0045(7) 0.0010(7) -0.0025(7) C15 0.0152(8) 0.0160(8) 0.0159(8) -0.0014(7) 0.0026(7) 0.0049(7) C16 0.0163(9) 0.0220(9) 0.0134(8) 0.0016(7) 0.0020(7) 0.0007(7) C17 0.0215(9) 0.0228(9) 0.0153(9) -0.0010(7) 0.0001(7) 0.0009(8) C18 0.0254(9) 0.0230(10) 0.0184(9) -0.0028(7) 0.0003(8) -0.0029(8) C19 0.0209(9) 0.0171(9) 0.0186(9) -0.0011(7) 0.0008(8) -0.0020(7) C20 0.0209(9) 0.0195(8) 0.0172(8) 0.0000(7) -0.0006(7) -0.0029(7) C21 0.0302(11) 0.0234(10) 0.0338(12) 0.0059(9) -0.0048(10) 0.0068(9) C22 0.0244(10) 0.0243(10) 0.0308(11) -0.0040(9) -0.0073(9) -0.0025(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.217(2) . ? O2 C8 1.2348(19) . ? O3 C15 1.239(2) . ? O4 C20 1.237(2) . ? N1 C1 1.366(2) . ? N1 C2 1.415(2) . ? N2 C8 1.350(2) . ? N2 C9 1.419(2) . ? N3 C15 1.347(2) . ? N3 C16 1.469(2) . ? N3 C19 1.484(2) . ? N4 C20 1.323(2) . ? N4 C21 1.456(2) . ? C1 C22 1.505(3) . ? C2 C3 1.403(2) . ? C2 C7 1.404(2) . ? C3 C4 1.396(2) . ? C3 C8 1.503(2) . ? C4 C5 1.379(3) . ? C5 C6 1.390(3) . ? C6 C7 1.381(3) . ? C9 C14 1.396(2) . ? C9 C10 1.400(2) . ? C10 C11 1.392(2) . ? C10 C15 1.503(2) . ? C11 C12 1.391(2) . ? C12 C13 1.388(3) . ? C13 C14 1.385(2) . ? C16 C20 1.526(2) . ? C16 C17 1.535(2) . ? C17 C18 1.528(3) . ? C18 C19 1.525(2) . ? 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 C2 126.81(15) . . ? C8 N2 C9 123.62(14) . . ? C15 N3 C16 121.86(14) . . ? C15 N3 C19 125.87(13) . . ? C16 N3 C19 112.26(13) . . ? C20 N4 C21 121.99(17) . . ? O1 C1 N1 124.13(17) . . ? O1 C1 C22 121.88(17) . . ? N1 C1 C22 113.99(16) . . ? C3 C2 C7 118.85(16) . . ? C3 C2 N1 118.87(15) . . ? C7 C2 N1 122.17(16) . . ? C4 C3 C2 119.63(16) . . ? C4 C3 C8 117.68(16) . . ? C2 C3 C8 122.67(15) . . ? C5 C4 C3 121.11(17) . . ? C4 C5 C6 119.21(17) . . ? C7 C6 C5 120.77(17) . . ? C6 C7 C2 120.37(18) . . ? O2 C8 N2 123.55(15) . . ? O2 C8 C3 120.86(15) . . ? N2 C8 C3 115.59(14) . . ? C14 C9 C10 119.79(16) . . ? C14 C9 N2 118.78(15) . . ? C10 C9 N2 121.40(15) . . ? C11 C10 C9 119.25(15) . . ? C11 C10 C15 118.92(15) . . ? C9 C10 C15 121.62(15) . . ? C12 C11 C10 121.00(16) . . ? C13 C12 C11 119.17(17) . . ? C14 C13 C12 120.75(16) . . ? C13 C14 C9 120.03(16) . . ? O3 C15 N3 121.79(15) . . ? O3 C15 C10 121.51(14) . . ? N3 C15 C10 116.67(14) . . ? N3 C16 C20 115.45(14) . . ? N3 C16 C17 102.44(13) . . ? C20 C16 C17 109.39(13) . . ? C18 C17 C16 102.79(14) . . ? C19 C18 C17 103.37(15) . . ? N3 C19 C18 102.75(14) . . ? O4 C20 N4 123.43(16) . . ? O4 C20 C16 118.08(16) . . ? N4 C20 C16 118.43(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 -1.0(3) . . . . ? C2 N1 C1 C22 179.16(16) . . . . ? C1 N1 C2 C3 161.76(16) . . . . ? C1 N1 C2 C7 -22.2(3) . . . . ? C7 C2 C3 C4 -0.6(2) . . . . ? N1 C2 C3 C4 175.51(15) . . . . ? C7 C2 C3 C8 -179.06(15) . . . . ? N1 C2 C3 C8 -2.9(2) . . . . ? C2 C3 C4 C5 2.5(3) . . . . ? C8 C3 C4 C5 -178.97(16) . . . . ? C3 C4 C5 C6 -2.0(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C2 2.2(3) . . . . ? C3 C2 C7 C6 -1.7(3) . . . . ? N1 C2 C7 C6 -177.69(16) . . . . ? C9 N2 C8 O2 -8.4(3) . . . . ? C9 N2 C8 C3 172.51(15) . . . . ? C4 C3 C8 O2 -50.8(2) . . . . ? C2 C3 C8 O2 127.70(17) . . . . ? C4 C3 C8 N2 128.32(16) . . . . ? C2 C3 C8 N2 -53.2(2) . . . . ? C8 N2 C9 C14 131.06(17) . . . . ? C8 N2 C9 C10 -50.9(2) . . . . ? C14 C9 C10 C11 1.3(2) . . . . ? N2 C9 C10 C11 -176.66(15) . . . . ? C14 C9 C10 C15 176.04(15) . . . . ? N2 C9 C10 C15 -2.0(2) . . . . ? C9 C10 C11 C12 -1.1(2) . . . . ? C15 C10 C11 C12 -175.97(15) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11 C12 C13 C14 1.2(3) . . . . ? C12 C13 C14 C9 -1.0(3) . . . . ? C10 C9 C14 C13 -0.3(2) . . . . ? N2 C9 C14 C13 177.78(15) . . . . ? C16 N3 C15 O3 -11.4(2) . . . . ? C19 N3 C15 O3 169.63(15) . . . . ? C16 N3 C15 C10 166.55(14) . . . . ? C19 N3 C15 C10 -12.4(2) . . . . ? C11 C10 C15 O3 118.20(18) . . . . ? C9 C10 C15 O3 -56.5(2) . . . . ? C11 C10 C15 N3 -59.8(2) . . . . ? C9 C10 C15 N3 125.48(17) . . . . ? C15 N3 C16 C20 77.30(19) . . . . ? C19 N3 C16 C20 -103.64(16) . . . . ? C15 N3 C16 C17 -163.92(14) . . . . ? C19 N3 C16 C17 15.13(17) . . . . ? N3 C16 C17 C18 -33.99(17) . . . . ? C20 C16 C17 C18 88.97(16) . . . . ? C16 C17 C18 C19 40.88(17) . . . . ? C15 N3 C19 C18 -171.05(15) . . . . ? C16 N3 C19 C18 9.94(18) . . . . ? C17 C18 C19 N3 -31.10(17) . . . . ? C21 N4 C20 O4 0.4(3) . . . . ? C21 N4 C20 C16 177.65(16) . . . . ? N3 C16 C20 O4 -171.86(15) . . . . ? C17 C16 C20 O4 73.29(19) . . . . ? N3 C16 C20 N4 10.7(2) . . . . ? C17 C16 C20 N4 -104.12(17) . . . . ? 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 N1 H1N O3 0.88(2) 2.12(2) 2.9754(19) 163.4(17) . N4 H4N O2 0.85(2) 2.12(2) 2.951(2) 164.6(18) . N2 H2N O4 0.87(2) 1.92(2) 2.7754(18) 164.8(19) 2_654 C12 H12 O1 0.985(19) 2.459(19) 3.414(2) 163.2(15) 1_565 C11 H11 O2 0.923(18) 2.591(18) 3.439(2) 152.9(13) 4_457 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.187 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.035 data_4 _database_code_depnum_ccdc_archive 'CCDC 858581' #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1323786906.cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N4 O5' _chemical_formula_sum 'C20 H20 N4 O5' _chemical_formula_weight 396.40 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.9252(7) _cell_length_b 8.9395(6) _cell_length_c 11.2908(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.821(2) _cell_angle_gamma 90.00 _cell_volume 984.09(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5609 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 28.77 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.78 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9273 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details 'Bruker SADABS' _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_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13960 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.82 _reflns_number_total 4884 _reflns_number_gt 4452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0353P)^2^+0.2008P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0052(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(8) _refine_ls_number_reflns 4884 _refine_ls_number_parameters 343 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 N1 N 0.23037(13) 0.60240(17) 0.73226(12) 0.0159(3) Uani 1 1 d . . . N2 N 0.34339(12) 0.94110(16) 0.75319(11) 0.0160(3) Uani 1 1 d . . . N3 N 0.39620(15) 0.98635(19) 1.09508(13) 0.0218(3) Uani 1 1 d . . . N4 N -0.12151(14) 0.66226(19) 0.72707(15) 0.0270(3) Uani 1 1 d . . . O1 O 0.05120(10) 0.43549(14) 0.63954(10) 0.0205(3) Uani 1 1 d . . . O2 O 0.53361(11) 0.80128(15) 0.86041(11) 0.0244(3) Uani 1 1 d . . . O3 O 0.31492(15) 0.79683(16) 0.95045(12) 0.0348(3) Uani 1 1 d . . . O4 O -0.08456(12) 0.71649(16) 0.64860(12) 0.0294(3) Uani 1 1 d . . . O5 O -0.23962(12) 0.6637(2) 0.71104(16) 0.0477(5) Uani 1 1 d . . . C1 C 0.12258(14) 0.52091(18) 0.72725(13) 0.0143(3) Uani 1 1 d . . . C2 C 0.28039(14) 0.60475(18) 0.63656(13) 0.0150(3) Uani 1 1 d . . . C3 C 0.37267(14) 0.71766(19) 0.64570(14) 0.0151(3) Uani 1 1 d . . . C4 C 0.42750(16) 0.7247(2) 0.55530(15) 0.0202(3) Uani 1 1 d . . . C5 C 0.38957(17) 0.6184(2) 0.45524(15) 0.0221(4) Uani 1 1 d . . . C6 C 0.29961(16) 0.5056(2) 0.44722(14) 0.0208(3) Uani 1 1 d . . . C7 C 0.24366(15) 0.4970(2) 0.53651(14) 0.0181(3) Uani 1 1 d . . . C8 C 0.42352(14) 0.82526(18) 0.76079(14) 0.0152(3) Uani 1 1 d . . . C9 C 0.36865(16) 1.02900(19) 0.87187(14) 0.0176(3) Uani 1 1 d . . . C10 C 0.25481(18) 1.1479(2) 0.81739(17) 0.0234(4) Uani 1 1 d . . . C11 C 0.13739(18) 1.0682(2) 0.70146(19) 0.0285(4) Uani 1 1 d . . . C12 C 0.21112(17) 0.9792(2) 0.63807(15) 0.0250(4) Uani 1 1 d . . . C13 C 0.35768(16) 0.9259(2) 0.97596(15) 0.0203(3) Uani 1 1 d . . . C14 C 0.3914(2) 0.8985(2) 1.20165(17) 0.0266(4) Uani 1 1 d . . . C15 C 0.10322(14) 0.53944(18) 0.85110(14) 0.0151(3) Uani 1 1 d . . . C16 C -0.01578(16) 0.5966(2) 0.84948(16) 0.0206(3) Uani 1 1 d . . . C17 C -0.03711(19) 0.6013(3) 0.96176(19) 0.0322(4) Uani 1 1 d . . . C18 C 0.0652(2) 0.5491(3) 1.08027(18) 0.0338(5) Uani 1 1 d . . . C19 C 0.18506(18) 0.4911(2) 1.08481(16) 0.0261(4) Uani 1 1 d . . . C20 C 0.20368(15) 0.4863(2) 0.97107(14) 0.0172(3) Uani 1 1 d . . . H1N H 0.260(2) 0.666(3) 0.793(2) 0.034(6) Uiso 1 1 d . . . H3N H 0.418(2) 1.073(3) 1.1073(18) 0.018(5) Uiso 1 1 d . . . H4 H 0.4887(17) 0.802(2) 0.5626(15) 0.011(4) Uiso 1 1 d . . . H5 H 0.4267(18) 0.620(2) 0.3933(17) 0.020(5) Uiso 1 1 d . . . H6 H 0.2754(17) 0.428(2) 0.3833(17) 0.020(5) Uiso 1 1 d . . . H7 H 0.1800(19) 0.415(2) 0.5271(17) 0.021(5) Uiso 1 1 d . . . H9 H 0.4593(19) 1.073(2) 0.9105(17) 0.018(4) Uiso 1 1 d . . . H10A H 0.289(2) 1.229(3) 0.7913(19) 0.025(5) Uiso 1 1 d . . . H10B H 0.2359(18) 1.180(2) 0.8882(18) 0.021(5) Uiso 1 1 d . . . H11A H 0.073(2) 1.144(3) 0.640(2) 0.043(6) Uiso 1 1 d . . . H11B H 0.087(2) 0.991(3) 0.7328(19) 0.028(5) Uiso 1 1 d . . . H12A H 0.166(2) 0.895(3) 0.595(2) 0.030(5) Uiso 1 1 d . . . H12B H 0.2310(19) 1.043(2) 0.5739(19) 0.025(5) Uiso 1 1 d . . . H14A H 0.300(2) 0.866(3) 1.174(2) 0.039(6) Uiso 1 1 d . . . H14B H 0.4176(19) 0.954(2) 1.2787(19) 0.025(5) Uiso 1 1 d . . . H14C H 0.453(3) 0.801(4) 1.220(2) 0.057(7) Uiso 1 1 d . . . H17 H -0.122(2) 0.646(3) 0.9509(18) 0.031(5) Uiso 1 1 d . . . H18 H 0.054(2) 0.559(3) 1.159(2) 0.039(6) Uiso 1 1 d . . . H19 H 0.2601(18) 0.453(2) 1.1712(18) 0.023(5) Uiso 1 1 d . . . H20 H 0.2870(18) 0.447(2) 0.9777(17) 0.020(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 N1 0.0176(6) 0.0159(7) 0.0142(5) -0.0053(5) 0.0072(5) -0.0047(6) N2 0.0150(6) 0.0163(7) 0.0135(5) -0.0004(5) 0.0036(5) -0.0002(5) N3 0.0315(7) 0.0128(7) 0.0184(6) -0.0043(6) 0.0088(5) -0.0061(7) N4 0.0209(7) 0.0239(8) 0.0364(8) 0.0084(7) 0.0132(6) 0.0056(6) O1 0.0177(5) 0.0226(7) 0.0188(5) -0.0038(5) 0.0061(4) -0.0059(5) O2 0.0197(5) 0.0173(6) 0.0230(5) -0.0027(5) -0.0020(4) -0.0001(5) O3 0.0636(9) 0.0222(7) 0.0268(6) -0.0108(6) 0.0277(6) -0.0219(7) O4 0.0282(6) 0.0297(8) 0.0304(6) 0.0127(6) 0.0133(5) 0.0101(6) O5 0.0172(6) 0.0530(11) 0.0717(10) 0.0298(9) 0.0189(7) 0.0117(7) C1 0.0124(6) 0.0141(8) 0.0147(6) 0.0016(6) 0.0046(5) 0.0018(6) C2 0.0147(6) 0.0166(8) 0.0129(6) -0.0002(6) 0.0055(5) 0.0005(6) C3 0.0147(6) 0.0141(8) 0.0138(6) 0.0000(6) 0.0040(5) 0.0009(6) C4 0.0186(7) 0.0212(9) 0.0217(7) 0.0019(7) 0.0098(6) -0.0011(7) C5 0.0258(8) 0.0261(10) 0.0185(7) 0.0016(7) 0.0136(6) 0.0008(7) C6 0.0238(7) 0.0223(9) 0.0162(6) -0.0033(7) 0.0089(6) 0.0010(7) C7 0.0194(7) 0.0172(8) 0.0161(6) -0.0022(6) 0.0067(5) -0.0009(7) C8 0.0157(7) 0.0128(8) 0.0161(6) 0.0004(6) 0.0063(5) -0.0039(6) C9 0.0196(7) 0.0146(8) 0.0172(6) -0.0037(6) 0.0070(6) -0.0035(7) C10 0.0274(8) 0.0162(9) 0.0266(8) -0.0033(7) 0.0121(7) 0.0012(7) C11 0.0193(8) 0.0253(10) 0.0348(9) -0.0059(8) 0.0068(7) 0.0046(8) C12 0.0189(7) 0.0276(10) 0.0189(7) -0.0033(8) 0.0001(6) 0.0066(8) C13 0.0240(7) 0.0178(8) 0.0194(7) -0.0026(6) 0.0101(6) -0.0032(7) C14 0.0390(10) 0.0233(10) 0.0178(7) -0.0037(7) 0.0131(7) -0.0060(9) C15 0.0156(6) 0.0121(8) 0.0180(6) -0.0013(6) 0.0080(6) -0.0034(6) C16 0.0165(7) 0.0201(9) 0.0258(7) 0.0055(7) 0.0101(6) 0.0022(7) C17 0.0316(9) 0.0355(12) 0.0425(10) 0.0067(9) 0.0280(8) 0.0074(9) C18 0.0412(10) 0.0416(13) 0.0284(9) 0.0042(9) 0.0244(8) 0.0031(10) C19 0.0313(8) 0.0280(10) 0.0200(7) 0.0033(8) 0.0124(7) -0.0009(8) C20 0.0164(7) 0.0161(8) 0.0183(6) -0.0013(6) 0.0070(6) -0.0021(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3640(19) . ? N1 C2 1.4140(17) . ? N1 H1N 0.83(2) . ? N2 C8 1.334(2) . ? N2 C9 1.4682(19) . ? N2 C12 1.4829(19) . ? N3 C13 1.329(2) . ? N3 C14 1.457(2) . ? N3 H3N 0.81(2) . ? N4 O5 1.2195(18) . ? N4 O4 1.2270(18) . ? N4 C16 1.466(2) . ? O1 C1 1.2145(18) . ? O2 C8 1.2397(18) . ? O3 C13 1.229(2) . ? C1 C15 1.5148(19) . ? C2 C3 1.397(2) . ? C2 C7 1.398(2) . ? C3 C4 1.399(2) . ? C3 C8 1.507(2) . ? C4 C5 1.388(2) . ? C4 H4 0.941(19) . ? C5 C6 1.383(3) . ? C5 H5 0.954(18) . ? C6 C7 1.397(2) . ? C6 H6 0.95(2) . ? C7 H7 0.98(2) . ? C9 C10 1.538(2) . ? C9 C13 1.540(2) . ? C9 H9 0.968(19) . ? C10 C11 1.534(3) . ? C10 H10A 0.92(2) . ? C10 H10B 0.955(18) . ? C11 C12 1.521(2) . ? C11 H11A 1.00(3) . ? C11 H11B 1.04(2) . ? C12 H12A 0.91(2) . ? C12 H12B 1.02(2) . ? C14 H14A 0.94(2) . ? C14 H14B 0.93(2) . ? C14 H14C 1.06(3) . ? C15 C20 1.387(2) . ? C15 C16 1.389(2) . ? C16 C17 1.389(2) . ? C17 C18 1.381(3) . ? C17 H17 0.96(2) . ? C18 C19 1.388(3) . ? C18 H18 0.95(2) . ? C19 C20 1.389(2) . ? C19 H19 1.009(19) . ? C20 H20 0.945(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 C1 N1 C2 126.90(13) . . ? C1 N1 H1N 114.1(14) . . ? C2 N1 H1N 118.3(15) . . ? C8 N2 C9 120.61(12) . . ? C8 N2 C12 125.93(13) . . ? C9 N2 C12 112.61(12) . . ? C13 N3 C14 120.22(17) . . ? C13 N3 H3N 120.0(13) . . ? C14 N3 H3N 119.7(13) . . ? O5 N4 O4 124.02(15) . . ? O5 N4 C16 118.36(15) . . ? O4 N4 C16 117.58(13) . . ? O1 C1 N1 126.46(13) . . ? O1 C1 C15 121.05(13) . . ? N1 C1 C15 112.39(12) . . ? C3 C2 C7 119.45(13) . . ? C3 C2 N1 117.97(13) . . ? C7 C2 N1 122.55(14) . . ? C2 C3 C4 120.72(14) . . ? C2 C3 C8 119.86(12) . . ? C4 C3 C8 119.21(14) . . ? C5 C4 C3 119.63(16) . . ? C5 C4 H4 121.0(10) . . ? C3 C4 H4 119.4(10) . . ? C6 C5 C4 119.65(14) . . ? C6 C5 H5 119.2(12) . . ? C4 C5 H5 121.1(12) . . ? C5 C6 C7 121.49(15) . . ? C5 C6 H6 121.9(11) . . ? C7 C6 H6 116.5(11) . . ? C6 C7 C2 119.05(15) . . ? C6 C7 H7 118.9(11) . . ? C2 C7 H7 122.1(11) . . ? O2 C8 N2 122.18(14) . . ? O2 C8 C3 120.09(14) . . ? N2 C8 C3 117.66(12) . . ? N2 C9 C10 102.70(12) . . ? N2 C9 C13 109.20(13) . . ? C10 C9 C13 113.05(13) . . ? N2 C9 H9 111.3(11) . . ? C10 C9 H9 112.1(12) . . ? C13 C9 H9 108.5(11) . . ? C11 C10 C9 103.55(14) . . ? C11 C10 H10A 113.3(12) . . ? C9 C10 H10A 107.4(13) . . ? C11 C10 H10B 116.1(11) . . ? C9 C10 H10B 108.3(11) . . ? H10A C10 H10B 107.8(18) . . ? C12 C11 C10 103.18(14) . . ? C12 C11 H11A 112.6(13) . . ? C10 C11 H11A 109.5(14) . . ? C12 C11 H11B 106.5(12) . . ? C10 C11 H11B 112.7(11) . . ? H11A C11 H11B 112.0(17) . . ? N2 C12 C11 102.78(13) . . ? N2 C12 H12A 110.9(14) . . ? C11 C12 H12A 114.1(13) . . ? N2 C12 H12B 108.4(11) . . ? C11 C12 H12B 111.8(12) . . ? H12A C12 H12B 108.6(17) . . ? O3 C13 N3 122.15(16) . . ? O3 C13 C9 122.35(14) . . ? N3 C13 C9 115.50(15) . . ? N3 C14 H14A 108.5(14) . . ? N3 C14 H14B 112.1(13) . . ? H14A C14 H14B 107.9(17) . . ? N3 C14 H14C 110.4(13) . . ? H14A C14 H14C 107(2) . . ? H14B C14 H14C 111.0(18) . . ? C20 C15 C16 117.54(13) . . ? C20 C15 C1 119.04(13) . . ? C16 C15 C1 123.21(13) . . ? C17 C16 C15 122.71(15) . . ? C17 C16 N4 117.60(14) . . ? C15 C16 N4 119.62(13) . . ? C18 C17 C16 118.58(16) . . ? C18 C17 H17 125.0(11) . . ? C16 C17 H17 116.4(12) . . ? C17 C18 C19 119.98(15) . . ? C17 C18 H18 119.0(13) . . ? C19 C18 H18 120.9(13) . . ? C18 C19 C20 120.46(15) . . ? C18 C19 H19 120.2(10) . . ? C20 C19 H19 119.3(10) . . ? C15 C20 C19 120.73(14) . . ? C15 C20 H20 120.9(11) . . ? C19 C20 H20 118.4(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 0.4(3) . . . . ? C2 N1 C1 C15 176.70(14) . . . . ? C1 N1 C2 C3 166.93(15) . . . . ? C1 N1 C2 C7 -14.7(2) . . . . ? C7 C2 C3 C4 0.6(2) . . . . ? N1 C2 C3 C4 178.99(14) . . . . ? C7 C2 C3 C8 -174.05(14) . . . . ? N1 C2 C3 C8 4.4(2) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C8 C3 C4 C5 174.80(15) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C4 C5 C6 C7 1.1(3) . . . . ? C5 C6 C7 C2 -0.4(2) . . . . ? C3 C2 C7 C6 -0.5(2) . . . . ? N1 C2 C7 C6 -178.80(14) . . . . ? C9 N2 C8 O2 -11.9(2) . . . . ? C12 N2 C8 O2 179.43(16) . . . . ? C9 N2 C8 C3 165.08(13) . . . . ? C12 N2 C8 C3 -3.6(2) . . . . ? C2 C3 C8 O2 94.96(18) . . . . ? C4 C3 C8 O2 -79.75(19) . . . . ? C2 C3 C8 N2 -82.09(18) . . . . ? C4 C3 C8 N2 103.21(16) . . . . ? C8 N2 C9 C10 179.77(14) . . . . ? C12 N2 C9 C10 -10.15(18) . . . . ? C8 N2 C9 C13 -59.99(17) . . . . ? C12 N2 C9 C13 110.09(15) . . . . ? N2 C9 C10 C11 30.21(16) . . . . ? C13 C9 C10 C11 -87.32(16) . . . . ? C9 C10 C11 C12 -39.45(18) . . . . ? C8 N2 C12 C11 155.31(15) . . . . ? C9 N2 C12 C11 -14.1(2) . . . . ? C10 C11 C12 N2 32.50(19) . . . . ? C14 N3 C13 O3 1.3(3) . . . . ? C14 N3 C13 C9 -179.37(15) . . . . ? N2 C9 C13 O3 -9.3(2) . . . . ? C10 C9 C13 O3 104.32(19) . . . . ? N2 C9 C13 N3 171.38(14) . . . . ? C10 C9 C13 N3 -74.97(18) . . . . ? O1 C1 C15 C20 110.68(17) . . . . ? N1 C1 C15 C20 -65.9(2) . . . . ? O1 C1 C15 C16 -64.0(2) . . . . ? N1 C1 C15 C16 119.47(17) . . . . ? C20 C15 C16 C17 -0.4(3) . . . . ? C1 C15 C16 C17 174.35(17) . . . . ? C20 C15 C16 N4 176.40(16) . . . . ? C1 C15 C16 N4 -8.9(3) . . . . ? O5 N4 C16 C17 -28.3(3) . . . . ? O4 N4 C16 C17 149.65(18) . . . . ? O5 N4 C16 C15 154.80(18) . . . . ? O4 N4 C16 C15 -27.3(3) . . . . ? C15 C16 C17 C18 1.1(3) . . . . ? N4 C16 C17 C18 -175.76(19) . . . . ? C16 C17 C18 C19 -1.2(3) . . . . ? C17 C18 C19 C20 0.6(3) . . . . ? C16 C15 C20 C19 -0.2(2) . . . . ? C1 C15 C20 C19 -175.17(16) . . . . ? C18 C19 C20 C15 0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.82 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.302 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.039 data_5 _database_code_depnum_ccdc_archive 'CCDC 858582' #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1323786906.cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H26 N4 O5' _chemical_formula_sum 'C23 H26 N4 O5' _chemical_formula_weight 438.48 _chemical_absolute_configuration syn 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.564(3) _cell_length_b 15.725(7) _cell_length_c 18.913(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2249.7(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5455 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.28 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9665 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details 'BRUKER SADABS' _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_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16193 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3957 _reflns_number_gt 3787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0224P)^2^+0.7706P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(12) _refine_ls_number_reflns 3957 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _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 O1 O 0.5790(2) 0.37348(10) 0.82335(8) 0.0294(4) Uani 1 1 d . . . O2 O 0.4688(2) 0.72205(10) 0.91805(8) 0.0193(4) Uani 1 1 d . . . O3 O 0.4052(2) 0.56324(9) 1.01145(8) 0.0202(4) Uani 1 1 d . . . O4 O 0.1946(2) 0.39273(11) 0.90750(9) 0.0304(4) Uani 1 1 d . . . O5 O 0.1141(2) 0.40064(12) 1.01753(10) 0.0380(5) Uani 1 1 d . . . N1 N 0.5031(2) 0.50282(11) 0.86956(10) 0.0150(4) Uani 1 1 d . . . N2 N 0.2225(2) 0.64133(11) 0.90664(9) 0.0152(4) Uani 1 1 d . . . N3 N 0.2884(3) 0.64902(13) 1.09633(10) 0.0196(4) Uani 1 1 d . . . N4 N 0.2251(3) 0.39013(12) 0.97135(11) 0.0250(5) Uani 1 1 d . . . C1 C 0.5383(3) 0.41915(14) 0.87274(12) 0.0179(5) Uani 1 1 d . . . C2 C 0.5031(3) 0.55472(14) 0.80806(11) 0.0158(5) Uani 1 1 d . . . C3 C 0.4405(3) 0.63813(14) 0.81393(11) 0.0150(5) Uani 1 1 d . . . C4 C 0.4408(3) 0.69212(15) 0.75577(12) 0.0203(5) Uani 1 1 d . . . C5 C 0.5022(3) 0.66311(15) 0.69129(13) 0.0230(5) Uani 1 1 d . . . C6 C 0.5668(3) 0.58161(15) 0.68559(13) 0.0230(5) Uani 1 1 d . . . C7 C 0.5695(3) 0.52734(15) 0.74313(12) 0.0190(5) Uani 1 1 d . . . C8 C 0.3774(3) 0.67198(13) 0.88365(11) 0.0148(5) Uani 1 1 d . . . C9 C 0.1642(3) 0.65582(14) 0.97950(11) 0.0169(5) Uani 1 1 d . . . H9 H 0.1464 0.7179 0.9885 0.020 Uiso 1 1 calc R . . C10 C -0.0134(3) 0.60784(15) 0.98326(12) 0.0219(5) Uani 1 1 d . . . H10A H 0.0035 0.5497 1.0021 0.026 Uiso 1 1 calc R . . H10B H -0.0987 0.6385 1.0137 0.026 Uiso 1 1 calc R . . C11 C -0.0780(3) 0.60503(15) 0.90684(12) 0.0225(5) Uani 1 1 d . . . H11A H -0.1384 0.6586 0.8938 0.027 Uiso 1 1 calc R . . H11B H -0.1600 0.5568 0.8993 0.027 Uiso 1 1 calc R . . C12 C 0.0927(3) 0.59335(14) 0.86426(12) 0.0202(5) Uani 1 1 d . . . H12A H 0.1257 0.5326 0.8607 0.024 Uiso 1 1 calc R . . H12B H 0.0812 0.6174 0.8161 0.024 Uiso 1 1 calc R . . C13 C 0.3004(3) 0.61883(13) 1.03095(11) 0.0174(5) Uani 1 1 d . . . C14 C 0.4001(3) 0.62272(15) 1.15731(11) 0.0212(5) Uani 1 1 d . . . C15 C 0.3319(4) 0.6722(2) 1.22099(14) 0.0338(7) Uani 1 1 d . . . C16 C 0.5918(3) 0.64617(18) 1.14220(14) 0.0271(6) Uani 1 1 d . . . C17 C 0.3834(4) 0.52757(17) 1.17048(14) 0.0278(6) Uani 1 1 d . . . C18 C 0.5466(3) 0.38255(13) 0.94682(12) 0.0174(5) Uani 1 1 d . . . C19 C 0.4067(3) 0.37081(14) 0.99355(12) 0.0217(5) Uani 1 1 d . . . C20 C 0.4285(3) 0.33709(14) 1.06063(12) 0.0226(5) Uani 1 1 d . . . C21 C 0.5961(4) 0.31307(14) 1.08183(13) 0.0239(5) Uani 1 1 d . . . C22 C 0.7368(3) 0.32328(15) 1.03675(13) 0.0240(6) Uani 1 1 d . . . C23 C 0.7135(3) 0.35797(14) 0.97002(12) 0.0205(5) Uani 1 1 d . . . H1N H 0.473(3) 0.5265(16) 0.9101(13) 0.025(7) Uiso 1 1 d . . . H3N H 0.208(3) 0.6872(15) 1.1040(12) 0.017(6) Uiso 1 1 d . . . H4 H 0.400(3) 0.7507(15) 0.7623(12) 0.021(6) Uiso 1 1 d . . . H5 H 0.501(3) 0.7019(15) 0.6528(12) 0.018(6) Uiso 1 1 d . . . H6 H 0.614(3) 0.5637(14) 0.6409(12) 0.015(6) Uiso 1 1 d . . . H7 H 0.614(3) 0.4711(15) 0.7378(11) 0.012(5) Uiso 1 1 d . . . H20 H 0.323(3) 0.3316(14) 1.0924(12) 0.015(6) Uiso 1 1 d . . . H21 H 0.603(3) 0.2893(15) 1.1250(13) 0.019(6) Uiso 1 1 d . . . H22 H 0.849(4) 0.3092(17) 1.0500(14) 0.035(8) Uiso 1 1 d . . . H23 H 0.813(3) 0.3663(14) 0.9367(11) 0.011(6) Uiso 1 1 d . . . H15A H 0.407(4) 0.6585(16) 1.2632(13) 0.028(7) Uiso 1 1 d . . . H15B H 0.347(4) 0.7332(19) 1.2142(14) 0.031(8) Uiso 1 1 d . . . H15C H 0.204(5) 0.662(2) 1.2312(16) 0.053(9) Uiso 1 1 d . . . H16A H 0.665(3) 0.6329(16) 1.1828(13) 0.023(6) Uiso 1 1 d . . . H16B H 0.605(4) 0.7113(18) 1.1323(14) 0.038(8) Uiso 1 1 d . . . H16C H 0.641(4) 0.6124(18) 1.1002(15) 0.041(8) Uiso 1 1 d . . . H17A H 0.461(3) 0.5157(15) 1.2140(13) 0.024(6) Uiso 1 1 d . . . H17B H 0.265(4) 0.5131(18) 1.1790(15) 0.041(8) Uiso 1 1 d . . . H17C H 0.429(4) 0.4972(16) 1.1297(14) 0.031(7) 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 0.0472(11) 0.0196(9) 0.0213(9) -0.0043(7) -0.0034(8) 0.0063(8) O2 0.0180(8) 0.0213(8) 0.0187(8) -0.0043(7) -0.0008(7) -0.0034(7) O3 0.0218(9) 0.0212(8) 0.0177(8) -0.0021(6) 0.0011(7) 0.0050(7) O4 0.0256(9) 0.0320(10) 0.0335(10) 0.0103(8) -0.0118(8) -0.0066(8) O5 0.0219(9) 0.0443(11) 0.0478(12) 0.0085(9) 0.0093(9) 0.0009(9) N1 0.0158(9) 0.0182(10) 0.0110(9) -0.0007(8) -0.0006(8) 0.0004(8) N2 0.0141(9) 0.0169(9) 0.0147(9) -0.0040(8) 0.0002(7) 0.0001(8) N3 0.0185(10) 0.0209(10) 0.0193(10) -0.0019(9) 0.0019(8) 0.0047(9) N4 0.0211(11) 0.0205(10) 0.0336(13) 0.0050(9) -0.0050(10) -0.0033(9) C1 0.0170(12) 0.0163(11) 0.0203(12) -0.0027(10) -0.0068(10) -0.0005(9) C2 0.0140(11) 0.0179(11) 0.0155(11) 0.0003(9) -0.0018(9) -0.0047(9) C3 0.0138(11) 0.0159(11) 0.0155(10) -0.0020(9) -0.0014(9) -0.0034(9) C4 0.0209(13) 0.0190(12) 0.0209(12) 0.0006(10) 0.0028(10) 0.0001(10) C5 0.0279(13) 0.0229(13) 0.0183(12) 0.0050(10) 0.0049(10) -0.0044(11) C6 0.0222(13) 0.0272(13) 0.0194(12) -0.0030(10) 0.0071(11) -0.0011(10) C7 0.0206(12) 0.0164(12) 0.0200(12) -0.0003(9) 0.0042(10) 0.0006(10) C8 0.0158(11) 0.0126(10) 0.0160(11) 0.0028(9) -0.0032(9) 0.0039(9) C9 0.0182(12) 0.0173(11) 0.0151(11) -0.0043(9) 0.0027(9) 0.0015(9) C10 0.0197(12) 0.0239(12) 0.0221(12) -0.0027(10) 0.0014(10) 0.0002(10) C11 0.0170(11) 0.0245(12) 0.0260(12) -0.0005(10) -0.0001(11) -0.0003(10) C12 0.0156(11) 0.0237(12) 0.0211(12) -0.0028(10) -0.0006(10) -0.0010(10) C13 0.0193(11) 0.0141(11) 0.0187(12) -0.0007(9) 0.0059(10) -0.0034(9) C14 0.0246(12) 0.0247(13) 0.0143(11) 0.0015(9) 0.0006(10) -0.0017(11) C15 0.0407(19) 0.0408(18) 0.0197(14) -0.0057(12) -0.0038(12) 0.0090(14) C16 0.0233(13) 0.0305(14) 0.0276(14) 0.0085(12) -0.0071(11) -0.0060(12) C17 0.0312(16) 0.0288(14) 0.0234(14) 0.0058(12) -0.0008(12) -0.0078(12) C18 0.0231(12) 0.0083(10) 0.0208(12) -0.0044(9) -0.0051(10) -0.0016(9) C19 0.0229(12) 0.0146(11) 0.0276(13) -0.0020(10) -0.0059(10) -0.0012(10) C20 0.0289(14) 0.0182(12) 0.0207(12) 0.0023(10) 0.0003(11) -0.0059(10) C21 0.0383(15) 0.0155(11) 0.0178(12) 0.0005(10) -0.0083(12) -0.0019(11) C22 0.0258(14) 0.0183(12) 0.0279(14) 0.0000(10) -0.0121(11) 0.0004(11) C23 0.0232(12) 0.0163(11) 0.0220(12) -0.0026(10) -0.0028(11) 0.0011(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 O1 C1 1.218(3) . ? O2 C8 1.233(3) . ? O3 C13 1.236(3) . ? O4 N4 1.230(3) . ? O5 N4 1.223(3) . ? N1 C1 1.344(3) . ? N1 C2 1.421(3) . ? N2 C8 1.340(3) . ? N2 C9 1.465(3) . ? N2 C12 1.475(3) . ? N3 C13 1.328(3) . ? N3 C14 1.488(3) . ? N4 C19 1.468(3) . ? C1 C18 1.516(3) . ? C2 C7 1.395(3) . ? C2 C3 1.399(3) . ? C3 C4 1.389(3) . ? C3 C8 1.500(3) . ? C4 C5 1.382(3) . ? C5 C6 1.376(3) . ? C6 C7 1.383(3) . ? C9 C13 1.532(3) . ? C9 C10 1.542(3) . ? C10 C11 1.526(3) . ? C11 C12 1.533(3) . ? C14 C16 1.523(4) . ? C14 C17 1.522(3) . ? C14 C15 1.524(3) . ? C18 C19 1.391(3) . ? C18 C23 1.392(3) . ? C19 C20 1.385(3) . ? C20 C21 1.382(4) . ? C21 C22 1.373(4) . ? C22 C23 1.386(3) . ? 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 C2 126.80(19) . . ? C8 N2 C9 120.86(18) . . ? C8 N2 C12 126.14(18) . . ? C9 N2 C12 112.98(17) . . ? C13 N3 C14 125.7(2) . . ? O5 N4 O4 124.6(2) . . ? O5 N4 C19 117.8(2) . . ? O4 N4 C19 117.6(2) . . ? O1 C1 N1 126.4(2) . . ? O1 C1 C18 118.33(19) . . ? N1 C1 C18 114.92(18) . . ? C7 C2 C3 118.8(2) . . ? C7 C2 N1 122.9(2) . . ? C3 C2 N1 118.28(19) . . ? C4 C3 C2 120.6(2) . . ? C4 C3 C8 118.7(2) . . ? C2 C3 C8 120.68(18) . . ? C5 C4 C3 119.8(2) . . ? C6 C5 C4 119.7(2) . . ? C5 C6 C7 121.2(2) . . ? C6 C7 C2 119.8(2) . . ? O2 C8 N2 123.3(2) . . ? O2 C8 C3 120.8(2) . . ? N2 C8 C3 115.85(18) . . ? N2 C9 C13 109.63(17) . . ? N2 C9 C10 103.27(17) . . ? C13 C9 C10 111.76(18) . . ? C11 C10 C9 104.43(18) . . ? C10 C11 C12 103.38(18) . . ? N2 C12 C11 102.34(17) . . ? O3 C13 N3 125.1(2) . . ? O3 C13 C9 120.68(19) . . ? N3 C13 C9 114.19(19) . . ? N3 C14 C16 109.13(19) . . ? N3 C14 C17 110.7(2) . . ? C16 C14 C17 110.4(2) . . ? N3 C14 C15 106.2(2) . . ? C16 C14 C15 110.3(2) . . ? C17 C14 C15 110.1(2) . . ? C19 C18 C23 116.9(2) . . ? C19 C18 C1 127.3(2) . . ? C23 C18 C1 115.7(2) . . ? C20 C19 C18 122.8(2) . . ? C20 C19 N4 116.9(2) . . ? C18 C19 N4 120.2(2) . . ? C21 C20 C19 118.7(2) . . ? C22 C21 C20 119.9(2) . . ? C21 C22 C23 120.9(2) . . ? C22 C23 C18 120.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 1.2(4) . . . . ? C2 N1 C1 C18 174.0(2) . . . . ? C1 N1 C2 C7 -11.1(4) . . . . ? C1 N1 C2 C3 171.8(2) . . . . ? C7 C2 C3 C4 1.4(3) . . . . ? N1 C2 C3 C4 178.7(2) . . . . ? C7 C2 C3 C8 -176.5(2) . . . . ? N1 C2 C3 C8 0.8(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C8 C3 C4 C5 178.5(2) . . . . ? C3 C4 C5 C6 -1.7(4) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C2 1.0(4) . . . . ? C3 C2 C7 C6 -2.2(3) . . . . ? N1 C2 C7 C6 -179.3(2) . . . . ? C9 N2 C8 O2 -9.3(3) . . . . ? C12 N2 C8 O2 169.0(2) . . . . ? C9 N2 C8 C3 167.57(18) . . . . ? C12 N2 C8 C3 -14.1(3) . . . . ? C4 C3 C8 O2 -73.1(3) . . . . ? C2 C3 C8 O2 104.9(2) . . . . ? C4 C3 C8 N2 109.9(2) . . . . ? C2 C3 C8 N2 -72.1(3) . . . . ? C8 N2 C9 C13 -58.9(3) . . . . ? C12 N2 C9 C13 122.62(19) . . . . ? C8 N2 C9 C10 -178.13(19) . . . . ? C12 N2 C9 C10 3.4(2) . . . . ? N2 C9 C10 C11 -24.7(2) . . . . ? C13 C9 C10 C11 -142.48(19) . . . . ? C9 C10 C11 C12 36.5(2) . . . . ? C8 N2 C12 C11 -159.4(2) . . . . ? C9 N2 C12 C11 19.0(2) . . . . ? C10 C11 C12 N2 -33.6(2) . . . . ? C14 N3 C13 O3 1.1(4) . . . . ? C14 N3 C13 C9 178.2(2) . . . . ? N2 C9 C13 O3 -21.2(3) . . . . ? C10 C9 C13 O3 92.7(2) . . . . ? N2 C9 C13 N3 161.50(18) . . . . ? C10 C9 C13 N3 -84.6(2) . . . . ? C13 N3 C14 C16 63.3(3) . . . . ? C13 N3 C14 C17 -58.3(3) . . . . ? C13 N3 C14 C15 -177.8(2) . . . . ? O1 C1 C18 C19 -116.6(3) . . . . ? N1 C1 C18 C19 69.9(3) . . . . ? O1 C1 C18 C23 63.2(3) . . . . ? N1 C1 C18 C23 -110.3(2) . . . . ? C23 C18 C19 C20 0.6(3) . . . . ? C1 C18 C19 C20 -179.6(2) . . . . ? C23 C18 C19 N4 -176.1(2) . . . . ? C1 C18 C19 N4 3.7(3) . . . . ? O5 N4 C19 C20 21.9(3) . . . . ? O4 N4 C19 C20 -156.5(2) . . . . ? O5 N4 C19 C18 -161.2(2) . . . . ? O4 N4 C19 C18 20.4(3) . . . . ? C18 C19 C20 C21 -0.8(3) . . . . ? N4 C19 C20 C21 176.0(2) . . . . ? C19 C20 C21 C22 0.3(3) . . . . ? C20 C21 C22 C23 0.4(4) . . . . ? C21 C22 C23 C18 -0.6(4) . . . . ? C19 C18 C23 C22 0.2(3) . . . . ? C1 C18 C23 C22 -179.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C22 H22 O5 0.91(3) 2.54(3) 3.124(3) 122(2) 1_655 C4 H4 O1 0.98(2) 2.53(2) 3.224(3) 128.2(18) 3_656 C11 H11B N1 0.99 2.74 3.622(3) 148.0 1_455 C9 H9 O2 1.00 2.41 3.103(3) 125.6 4_467 C10 H10B O2 0.99 2.60 3.265(3) 124.9 4_467 N3 H3N O2 0.87(3) 2.34(3) 3.167(3) 159(2) 4_467 N1 H1N O3 0.88(3) 2.07(3) 2.941(3) 171(2) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.197 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.040 data_6 _database_code_depnum_ccdc_archive 'CCDC 858583' #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1323786906.cifs.cif' # start Validation Reply Form _vrf_PLAT331_I ; PROBLEM: Small Average Phenyl C-C Dist. C26 -C31 1.34 Ang. RESPONSE: This error is due to the solvent benzene molecule which is exhibiting thermal disorder. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H27 Br N4 O5' _chemical_formula_sum 'C31 H27 Br N4 O5' _chemical_formula_weight 615.48 _chemical_absolute_configuration rmad 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' Br Br -0.2901 2.4595 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.628(3) _cell_length_b 11.943(4) _cell_length_c 12.282(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.847(6) _cell_angle_gamma 90.00 _cell_volume 1411.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 5290 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.11 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6696 _exptl_absorpt_correction_T_max 0.8171 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7184 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4873 _reflns_number_gt 4521 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(6) _refine_ls_number_reflns 4873 _refine_ls_number_parameters 382 _refine_ls_number_restraints 49 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 1.000 _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 Br1 Br 0.86630(2) 0.28710(3) 0.08606(3) 0.04356(10) Uani 1 1 d . . . O1 O 0.18668(17) 0.87847(16) 0.21558(17) 0.0354(4) Uani 1 1 d . . . O2 O 0.69471(17) 1.02251(15) 0.02886(13) 0.0264(4) Uani 1 1 d . . . O3 O 0.67381(17) 0.82901(14) 0.21472(15) 0.0296(4) Uani 1 1 d . . . O4 O 0.3918(2) 0.91618(17) 0.42020(17) 0.0456(5) Uani 1 1 d . . . O5 O 0.4660(3) 0.7975(3) 0.53983(16) 0.0595(6) Uani 1 1 d . . . N1 N 0.4088(2) 0.93607(18) 0.18242(18) 0.0243(5) Uani 1 1 d . . . N2 N 0.7150(2) 1.04859(16) 0.20888(16) 0.0215(4) Uani 1 1 d . . . N3 N 0.89950(19) 0.7846(2) 0.18572(16) 0.0250(4) Uani 1 1 d . . . N4 N 0.4269(2) 0.82154(19) 0.44758(19) 0.0352(6) Uani 1 1 d . . . C1 C 0.3129(2) 0.8646(2) 0.2192(2) 0.0237(5) Uani 1 1 d . . . C2 C 0.3877(2) 1.0470(2) 0.1445(2) 0.0236(5) Uani 1 1 d . . . C3 C 0.5031(2) 1.1090(2) 0.11390(18) 0.0211(5) Uani 1 1 d . . . C4 C 0.4861(3) 1.2174(2) 0.0751(2) 0.0248(5) Uani 1 1 d . . . H4 H 0.5648 1.2586 0.0531 0.030 Uiso 1 1 calc R . . C5 C 0.3555(2) 1.2663(2) 0.0679(2) 0.0294(7) Uani 1 1 d . . . H5 H 0.3444 1.3411 0.0429 0.035 Uiso 1 1 calc R . . C6 C 0.2423(3) 1.2045(2) 0.0979(2) 0.0345(6) Uani 1 1 d . . . H6 H 0.1525 1.2372 0.0919 0.041 Uiso 1 1 calc R . . C7 C 0.2558(3) 1.0964(2) 0.1364(2) 0.0328(6) Uani 1 1 d . . . H7 H 0.1762 1.0557 0.1573 0.039 Uiso 1 1 calc R . . C8 C 0.6456(2) 1.05726(19) 0.11403(19) 0.0202(5) Uani 1 1 d . . . C9 C 0.8411(3) 0.9800(2) 0.2179(2) 0.0243(5) Uani 1 1 d . . . C10 C 0.8969(3) 1.0074(2) 0.3324(2) 0.0322(6) Uani 1 1 d . . . H10A H 0.9523 0.9445 0.3632 0.039 Uiso 1 1 calc R . . H10B H 0.9554 1.0756 0.3322 0.039 Uiso 1 1 calc R . . C11 C 0.7662(3) 1.0263(3) 0.3962(2) 0.0354(6) Uani 1 1 d . . . H11A H 0.7865 1.0705 0.4630 0.042 Uiso 1 1 calc R . . H11B H 0.7231 0.9543 0.4165 0.042 Uiso 1 1 calc R . . C12 C 0.6726(3) 1.0913(2) 0.3161(2) 0.0308(6) Uani 1 1 d . . . H12A H 0.5732 1.0756 0.3280 0.037 Uiso 1 1 calc R . . H12B H 0.6889 1.1730 0.3224 0.037 Uiso 1 1 calc R . . C13 C 0.7959(2) 0.8572(2) 0.20537(19) 0.0230(5) Uani 1 1 d . . . C14 C 0.8880(2) 0.6682(2) 0.1667(2) 0.0233(5) Uani 1 1 d . . . C15 C 1.0041(2) 0.6129(2) 0.1307(2) 0.0298(6) Uani 1 1 d . . . H15 H 1.0882 0.6531 0.1225 0.036 Uiso 1 1 calc R . . C16 C 0.9996(3) 0.4996(2) 0.1062(2) 0.0303(6) Uani 1 1 d . . . H16 H 1.0794 0.4622 0.0808 0.036 Uiso 1 1 calc R . . C17 C 0.8772(2) 0.4424(2) 0.1196(2) 0.0292(6) Uani 1 1 d . . . C18 C 0.7615(3) 0.4953(2) 0.1573(3) 0.0393(7) Uani 1 1 d . . . H18 H 0.6785 0.4540 0.1671 0.047 Uiso 1 1 calc R . . C19 C 0.7652(3) 0.6090(2) 0.1811(3) 0.0392(7) Uani 1 1 d . . . H19 H 0.6852 0.6458 0.2069 0.047 Uiso 1 1 calc R . . C20 C 0.3696(2) 0.75377(19) 0.26050(19) 0.0217(5) Uani 1 1 d . . . C21 C 0.4195(2) 0.7316(2) 0.3659(2) 0.0262(5) Uani 1 1 d . . . C22 C 0.4597(3) 0.6265(2) 0.3998(2) 0.0310(6) Uani 1 1 d . . . H22 H 0.4931 0.6145 0.4725 0.037 Uiso 1 1 calc R . . C23 C 0.4507(3) 0.5380(2) 0.3265(2) 0.0305(6) Uani 1 1 d . . . H23 H 0.4774 0.4647 0.3487 0.037 Uiso 1 1 calc R . . C24 C 0.4029(2) 0.5573(2) 0.2215(2) 0.0278(5) Uani 1 1 d . . . H24 H 0.3967 0.4971 0.1711 0.033 Uiso 1 1 calc R . . C25 C 0.3640(3) 0.6636(2) 0.1889(2) 0.0237(5) Uani 1 1 d . . . H25 H 0.3326 0.6755 0.1157 0.028 Uiso 1 1 calc R . . H1N H 0.484(3) 0.920(3) 0.191(2) 0.031(8) Uiso 1 1 d . . . H3N H 0.980(2) 0.810(2) 0.1832(18) 0.015(6) Uiso 1 1 d . . . H9 H 0.910(3) 0.991(2) 0.161(2) 0.020(6) Uiso 1 1 d . . . C26 C 0.8755(6) 0.8063(6) 0.6321(4) 0.0927(17) Uani 1 1 d U . . H26 H 0.8362 0.8405 0.6938 0.111 Uiso 1 1 calc R . . C27 C 1.0009(8) 0.8418(5) 0.5976(5) 0.109(2) Uani 1 1 d U . . H27 H 1.0521 0.8998 0.6334 0.130 Uiso 1 1 calc R . . C28 C 1.0511(5) 0.7847(9) 0.5018(6) 0.117(2) Uani 1 1 d U . . H28 H 1.1376 0.8037 0.4717 0.141 Uiso 1 1 calc R . . C29 C 0.9691(10) 0.7033(7) 0.4576(4) 0.116(3) Uani 1 1 d U . . H29 H 0.9992 0.6636 0.3956 0.139 Uiso 1 1 calc R . . C30 C 0.8545(8) 0.6796(6) 0.4970(6) 0.120(2) Uani 1 1 d U . . H30 H 0.7988 0.6240 0.4616 0.145 Uiso 1 1 calc R . . C31 C 0.8088(5) 0.7258(7) 0.5813(6) 0.108(2) Uani 1 1 d U . . H31 H 0.7229 0.7009 0.6086 0.129 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 Br1 0.02316(13) 0.02321(13) 0.0844(2) -0.01170(15) 0.00305(12) 0.00045(12) O1 0.0171(9) 0.0279(10) 0.0613(13) 0.0057(9) 0.0043(8) -0.0015(8) O2 0.0229(8) 0.0268(9) 0.0296(9) -0.0013(7) 0.0038(7) 0.0018(7) O3 0.0175(9) 0.0226(8) 0.0487(11) 0.0022(7) 0.0031(8) -0.0007(6) O4 0.0655(15) 0.0305(12) 0.0409(12) -0.0057(9) 0.0006(11) -0.0015(10) O5 0.0908(16) 0.0508(14) 0.0355(11) -0.0089(12) -0.0187(11) -0.0019(15) N1 0.0130(11) 0.0227(12) 0.0372(12) 0.0061(9) 0.0002(9) 0.0013(9) N2 0.0188(10) 0.0179(10) 0.0278(11) -0.0014(8) 0.0004(8) 0.0010(8) N3 0.0134(9) 0.0204(9) 0.0414(11) 0.0017(11) 0.0025(8) -0.0021(11) N4 0.0364(12) 0.0348(15) 0.0341(13) -0.0044(10) -0.0024(10) -0.0067(10) C1 0.0202(13) 0.0239(12) 0.0267(13) -0.0016(10) -0.0009(10) -0.0007(10) C2 0.0209(11) 0.0205(12) 0.0293(13) 0.0007(10) -0.0012(10) 0.0018(10) C3 0.0200(11) 0.0211(12) 0.0220(12) -0.0019(9) -0.0009(9) 0.0007(9) C4 0.0246(12) 0.0225(13) 0.0273(12) 0.0007(10) 0.0006(10) 0.0014(10) C5 0.0283(12) 0.0250(19) 0.0347(14) 0.0015(10) -0.0032(11) 0.0041(10) C6 0.0218(13) 0.0297(14) 0.0514(17) 0.0035(12) -0.0052(12) 0.0092(11) C7 0.0184(12) 0.0285(14) 0.0518(17) 0.0037(12) 0.0036(11) 0.0016(11) C8 0.0203(11) 0.0139(10) 0.0265(13) 0.0016(9) 0.0010(10) -0.0024(9) C9 0.0164(12) 0.0223(13) 0.0341(14) 0.0034(10) -0.0008(11) 0.0010(10) C10 0.0257(13) 0.0291(14) 0.0413(15) -0.0045(11) -0.0090(12) 0.0015(11) C11 0.0346(14) 0.0416(17) 0.0296(14) -0.0019(12) -0.0060(12) -0.0001(12) C12 0.0273(13) 0.0364(15) 0.0286(13) -0.0061(11) -0.0011(11) 0.0032(11) C13 0.0184(12) 0.0228(13) 0.0278(13) 0.0025(9) -0.0012(10) -0.0019(10) C14 0.0198(12) 0.0204(12) 0.0298(13) 0.0021(10) 0.0001(10) -0.0008(10) C15 0.0157(12) 0.0253(13) 0.0483(16) 0.0054(11) 0.0013(11) -0.0041(10) C16 0.0182(12) 0.0239(13) 0.0491(17) 0.0024(11) 0.0063(11) 0.0042(10) C17 0.0236(13) 0.0169(12) 0.0470(15) 0.0003(11) -0.0002(11) -0.0007(10) C18 0.0193(13) 0.0239(14) 0.075(2) -0.0085(14) 0.0106(14) -0.0044(11) C19 0.0224(13) 0.0305(16) 0.065(2) -0.0091(14) 0.0130(13) -0.0039(12) C20 0.0160(10) 0.0224(12) 0.0271(13) 0.0010(9) 0.0061(9) -0.0043(9) C21 0.0209(12) 0.0282(13) 0.0296(13) -0.0035(10) 0.0026(10) -0.0049(10) C22 0.0303(14) 0.0355(15) 0.0273(14) 0.0066(11) 0.0002(11) -0.0027(12) C23 0.0255(13) 0.0283(14) 0.0378(14) 0.0088(11) 0.0038(11) 0.0012(11) C24 0.0221(12) 0.0225(13) 0.0391(15) -0.0034(11) 0.0032(11) -0.0024(10) C25 0.0180(13) 0.0287(14) 0.0243(13) 0.0008(10) 0.0006(10) -0.0025(10) C26 0.107(4) 0.115(5) 0.057(2) 0.009(3) 0.009(2) 0.048(3) C27 0.133(5) 0.088(4) 0.101(4) 0.042(3) -0.067(4) -0.024(3) C28 0.051(2) 0.181(6) 0.121(4) 0.118(4) 0.025(3) 0.030(3) C29 0.162(6) 0.138(6) 0.046(3) 0.018(3) -0.002(3) 0.106(5) C30 0.146(6) 0.105(5) 0.105(5) 0.000(4) -0.077(4) 0.016(4) C31 0.052(3) 0.155(6) 0.115(4) 0.057(4) -0.015(3) 0.010(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 Br1 C17 1.902(3) . ? O1 C1 1.226(3) . ? O2 C8 1.234(3) . ? O3 C13 1.232(3) . ? O4 N4 1.224(3) . ? O5 N4 1.217(3) . ? N1 C1 1.346(3) . ? N1 C2 1.417(3) . ? N2 C8 1.328(3) . ? N2 C9 1.466(3) . ? N2 C12 1.482(3) . ? N3 C13 1.349(3) . ? N3 C14 1.413(4) . ? N4 C21 1.470(3) . ? C1 C20 1.513(4) . ? C2 C3 1.397(3) . ? C2 C7 1.401(3) . ? C3 C4 1.387(3) . ? C3 C8 1.505(3) . ? C4 C5 1.386(3) . ? C5 C6 1.375(4) . ? C6 C7 1.381(4) . ? C9 C10 1.524(4) . ? C9 C13 1.537(3) . ? C10 C11 1.521(4) . ? C11 C12 1.526(4) . ? C14 C15 1.384(4) . ? C14 C19 1.394(4) . ? C15 C16 1.386(4) . ? C16 C17 1.377(4) . ? C17 C18 1.374(4) . ? C18 C19 1.389(4) . ? C20 C25 1.390(3) . ? C20 C21 1.391(4) . ? C21 C22 1.374(4) . ? C22 C23 1.390(4) . ? C23 C24 1.375(4) . ? C24 C25 1.379(4) . ? C26 C31 1.304(9) . ? C26 C27 1.360(8) . ? C27 C28 1.455(11) . ? C28 C29 1.354(10) . ? C29 C30 1.252(10) . ? C30 C31 1.265(9) . ? 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 C2 127.7(2) . . ? C8 N2 C9 120.1(2) . . ? C8 N2 C12 127.4(2) . . ? C9 N2 C12 112.16(19) . . ? C13 N3 C14 127.4(2) . . ? O5 N4 O4 123.3(3) . . ? O5 N4 C21 118.0(2) . . ? O4 N4 C21 118.7(2) . . ? O1 C1 N1 126.3(3) . . ? O1 C1 C20 118.5(2) . . ? N1 C1 C20 115.0(2) . . ? C3 C2 C7 119.0(2) . . ? C3 C2 N1 118.5(2) . . ? C7 C2 N1 122.5(2) . . ? C4 C3 C2 120.1(2) . . ? C4 C3 C8 118.8(2) . . ? C2 C3 C8 121.0(2) . . ? C5 C4 C3 120.8(2) . . ? C6 C5 C4 118.8(2) . . ? C5 C6 C7 121.8(2) . . ? C6 C7 C2 119.5(2) . . ? O2 C8 N2 121.5(2) . . ? O2 C8 C3 120.8(2) . . ? N2 C8 C3 117.8(2) . . ? N2 C9 C10 102.5(2) . . ? N2 C9 C13 107.14(19) . . ? C10 C9 C13 112.8(2) . . ? C11 C10 C9 103.6(2) . . ? C10 C11 C12 103.0(2) . . ? N2 C12 C11 102.9(2) . . ? O3 C13 N3 123.7(2) . . ? O3 C13 C9 121.3(2) . . ? N3 C13 C9 115.0(2) . . ? C15 C14 C19 119.7(2) . . ? C15 C14 N3 117.6(2) . . ? C19 C14 N3 122.8(2) . . ? C14 C15 C16 121.1(2) . . ? C17 C16 C15 118.6(2) . . ? C18 C17 C16 121.2(2) . . ? C18 C17 Br1 118.81(19) . . ? C16 C17 Br1 119.96(19) . . ? C17 C18 C19 120.3(2) . . ? C18 C19 C14 119.1(3) . . ? C25 C20 C21 116.5(2) . . ? C25 C20 C1 117.3(2) . . ? C21 C20 C1 126.0(2) . . ? C22 C21 C20 122.8(2) . . ? C22 C21 N4 116.9(2) . . ? C20 C21 N4 120.3(2) . . ? C21 C22 C23 119.2(2) . . ? C24 C23 C22 119.5(2) . . ? C23 C24 C25 120.4(2) . . ? C24 C25 C20 121.6(2) . . ? C31 C26 C27 120.6(6) . . ? C26 C27 C28 115.3(6) . . ? C29 C28 C27 117.1(5) . . ? C30 C29 C28 121.1(6) . . ? C29 C30 C31 123.5(8) . . ? C30 C31 C26 122.3(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 C2 N1 C1 O1 8.5(4) . . . . ? C2 N1 C1 C20 -176.5(2) . . . . ? C1 N1 C2 C3 177.3(2) . . . . ? C1 N1 C2 C7 -2.8(4) . . . . ? C7 C2 C3 C4 -0.7(4) . . . . ? N1 C2 C3 C4 179.2(2) . . . . ? C7 C2 C3 C8 -175.9(2) . . . . ? N1 C2 C3 C8 4.0(3) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C8 C3 C4 C5 176.5(2) . . . . ? C3 C4 C5 C6 -1.4(4) . . . . ? C4 C5 C6 C7 1.1(4) . . . . ? C5 C6 C7 C2 -0.7(4) . . . . ? C3 C2 C7 C6 0.4(4) . . . . ? N1 C2 C7 C6 -179.4(2) . . . . ? C9 N2 C8 O2 -10.7(3) . . . . ? C12 N2 C8 O2 176.7(2) . . . . ? C9 N2 C8 C3 168.1(2) . . . . ? C12 N2 C8 C3 -4.5(4) . . . . ? C4 C3 C8 O2 -76.2(3) . . . . ? C2 C3 C8 O2 99.1(3) . . . . ? C4 C3 C8 N2 105.0(3) . . . . ? C2 C3 C8 N2 -79.8(3) . . . . ? C8 N2 C9 C10 171.9(2) . . . . ? C12 N2 C9 C10 -14.5(3) . . . . ? C8 N2 C9 C13 -69.1(3) . . . . ? C12 N2 C9 C13 104.5(2) . . . . ? N2 C9 C10 C11 33.5(3) . . . . ? C13 C9 C10 C11 -81.4(3) . . . . ? C9 C10 C11 C12 -40.4(3) . . . . ? C8 N2 C12 C11 162.8(2) . . . . ? C9 N2 C12 C11 -10.3(3) . . . . ? C10 C11 C12 N2 30.8(3) . . . . ? C14 N3 C13 O3 3.7(4) . . . . ? C14 N3 C13 C9 -177.4(2) . . . . ? N2 C9 C13 O3 -16.2(3) . . . . ? C10 C9 C13 O3 95.9(3) . . . . ? N2 C9 C13 N3 164.9(2) . . . . ? C10 C9 C13 N3 -83.0(3) . . . . ? C13 N3 C14 C15 169.6(2) . . . . ? C13 N3 C14 C19 -9.3(4) . . . . ? C19 C14 C15 C16 1.4(4) . . . . ? N3 C14 C15 C16 -177.5(2) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? C15 C16 C17 C18 -0.6(4) . . . . ? C15 C16 C17 Br1 179.6(2) . . . . ? C16 C17 C18 C19 1.1(5) . . . . ? Br1 C17 C18 C19 -179.1(2) . . . . ? C17 C18 C19 C14 -0.3(5) . . . . ? C15 C14 C19 C18 -0.9(4) . . . . ? N3 C14 C19 C18 178.0(3) . . . . ? O1 C1 C20 C25 78.5(3) . . . . ? N1 C1 C20 C25 -97.0(3) . . . . ? O1 C1 C20 C21 -97.4(3) . . . . ? N1 C1 C20 C21 87.2(3) . . . . ? C25 C20 C21 C22 -1.0(4) . . . . ? C1 C20 C21 C22 174.9(2) . . . . ? C25 C20 C21 N4 -179.0(2) . . . . ? C1 C20 C21 N4 -3.2(4) . . . . ? O5 N4 C21 C22 -1.0(4) . . . . ? O4 N4 C21 C22 -179.9(3) . . . . ? O5 N4 C21 C20 177.1(2) . . . . ? O4 N4 C21 C20 -1.8(4) . . . . ? C20 C21 C22 C23 0.1(4) . . . . ? N4 C21 C22 C23 178.2(2) . . . . ? C21 C22 C23 C24 0.4(4) . . . . ? C22 C23 C24 C25 0.0(4) . . . . ? C23 C24 C25 C20 -1.0(4) . . . . ? C21 C20 C25 C24 1.4(4) . . . . ? C1 C20 C25 C24 -174.8(2) . . . . ? C31 C26 C27 C28 0.6(7) . . . . ? C26 C27 C28 C29 0.0(7) . . . . ? C27 C28 C29 C30 0.9(8) . . . . ? C28 C29 C30 C31 -2.4(9) . . . . ? C29 C30 C31 C26 3.1(10) . . . . ? C27 C26 C31 C30 -2.1(9) . . . . ? 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 C23 H23 O5 0.95 2.47 3.392(4) 163.0 2_646 C16 H16 O2 0.95 2.69 3.436(3) 135.5 2_745 C5 H5 O2 0.95 2.36 3.312(3) 176.0 2_655 N3 H3N O1 0.84(2) 2.17(2) 2.995(3) 167(2) 1_655 N1 H1N O3 0.76(3) 2.14(3) 2.870(3) 165(3) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.706 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.052 data_7 _database_code_depnum_ccdc_archive 'CCDC 858584' #TrackingRef 'web_deposit_cif_file_0_Dr.RajeshG.Gonnade_1323786906.cifs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N3 O3' _chemical_formula_sum 'C20 H21 N3 O3' _chemical_formula_weight 351.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 21.610(3) _cell_length_b 8.6706(12) _cell_length_c 21.210(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.719(2) _cell_angle_gamma 90.00 _cell_volume 3485.2(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6611 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 27.99 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9466 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'Bruker SADABS' _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_device 'BRUKER SMART APEX' _diffrn_measurement_method 'Omega and phi Scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17077 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6121 _reflns_number_gt 5518 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SAINT' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0459P)^2^+2.2021P] 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 6121 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 0.47180(7) 0.35129(17) 0.61060(7) 0.0264(3) Uani 1 1 d . . . O2 O 0.36424(6) 0.37844(15) 0.34102(6) 0.0185(3) Uani 1 1 d . . . O3 O 0.37072(6) 0.02570(16) 0.34175(6) 0.0189(3) Uani 1 1 d . . . N1 N 0.42133(8) 0.38340(19) 0.48883(8) 0.0185(3) Uani 1 1 d . . . H1N H 0.4284 0.3666 0.4519 0.022 Uiso 1 1 calc R . . N2 N 0.25231(7) 0.28679(18) 0.29675(7) 0.0155(3) Uani 1 1 d . . . H2N H 0.2170 0.2776 0.3062 0.019 Uiso 1 1 calc R . . N3 N 0.42471(7) 0.13788(18) 0.28562(7) 0.0161(3) Uani 1 1 d . . . C1 C 0.47388(9) 0.3362(2) 0.55427(9) 0.0196(4) Uani 1 1 d . . . C2 C 0.35728(9) 0.4556(2) 0.47355(9) 0.0167(4) Uani 1 1 d . . . C3 C 0.30042(9) 0.4453(2) 0.40317(9) 0.0164(4) Uani 1 1 d . . . C4 C 0.23704(9) 0.5198(2) 0.38669(9) 0.0183(4) Uani 1 1 d . . . H4 H 0.1983 0.5116 0.3395 0.022 Uiso 1 1 calc R . . C5 C 0.22972(10) 0.6053(2) 0.43800(10) 0.0207(4) Uani 1 1 d . . . H5 H 0.1866 0.6565 0.4260 0.025 Uiso 1 1 calc R . . C6 C 0.28606(10) 0.6150(2) 0.50690(10) 0.0206(4) Uani 1 1 d . . . H6 H 0.2815 0.6739 0.5422 0.025 Uiso 1 1 calc R . . C7 C 0.34899(9) 0.5400(2) 0.52500(9) 0.0196(4) Uani 1 1 d . . . H7 H 0.3868 0.5461 0.5728 0.024 Uiso 1 1 calc R . . C8 C 0.30908(9) 0.3662(2) 0.34477(9) 0.0161(4) Uani 1 1 d . . . C9 C 0.24348(9) 0.2163(2) 0.23252(9) 0.0153(4) Uani 1 1 d . . . C10 C 0.29643(9) 0.1351(2) 0.22635(9) 0.0152(4) Uani 1 1 d . . . C11 C 0.27986(9) 0.0662(2) 0.16046(9) 0.0172(4) Uani 1 1 d . . . H11 H 0.3155 0.0120 0.1555 0.021 Uiso 1 1 calc R . . C12 C 0.21272(9) 0.0754(2) 0.10248(9) 0.0191(4) Uani 1 1 d . . . H12 H 0.2023 0.0262 0.0585 0.023 Uiso 1 1 calc R . . C13 C 0.16057(9) 0.1569(2) 0.10867(9) 0.0194(4) Uani 1 1 d . . . H13 H 0.1144 0.1643 0.0689 0.023 Uiso 1 1 calc R . . C14 C 0.17636(9) 0.2271(2) 0.17328(9) 0.0180(4) Uani 1 1 d . . . H14 H 0.1408 0.2836 0.1773 0.022 Uiso 1 1 calc R . . C15 C 0.36697(9) 0.0996(2) 0.28971(9) 0.0155(4) Uani 1 1 d . . . C16 C 0.49448(9) 0.1049(2) 0.34681(9) 0.0193(4) Uani 1 1 d . . . H16A H 0.5021 -0.0075 0.3552 0.023 Uiso 1 1 calc R . . H16B H 0.5002 0.1551 0.3912 0.023 Uiso 1 1 calc R . . C17 C 0.54482(9) 0.1738(2) 0.32291(10) 0.0210(4) Uani 1 1 d . . . H17A H 0.5898 0.2057 0.3648 0.025 Uiso 1 1 calc R . . H17B H 0.5550 0.0991 0.2938 0.025 Uiso 1 1 calc R . . C18 C 0.50451(9) 0.3128(2) 0.27798(10) 0.0224(4) Uani 1 1 d . . . H18A H 0.5226 0.3447 0.2451 0.027 Uiso 1 1 calc R . . H18B H 0.5077 0.4012 0.3090 0.027 Uiso 1 1 calc R . . C19 C 0.42871(9) 0.2531(2) 0.23612(9) 0.0184(4) Uani 1 1 d . . . H19A H 0.3942 0.3373 0.2258 0.022 Uiso 1 1 calc R . . H19B H 0.4199 0.2046 0.1903 0.022 Uiso 1 1 calc R . . C20 C 0.53564(10) 0.2622(3) 0.55223(10) 0.0273(5) Uani 1 1 d . . . H20A H 0.5793 0.3133 0.5869 0.041 Uiso 1 1 calc R . . H20B H 0.5303 0.2723 0.5038 0.041 Uiso 1 1 calc R . . H20C H 0.5377 0.1528 0.5646 0.041 Uiso 1 1 calc R . . O1' O 0.01195(8) 0.8134(2) 0.02880(7) 0.0438(4) Uani 1 1 d . . . O2' O 0.13605(6) 0.84808(16) 0.29739(6) 0.0198(3) Uani 1 1 d . . . O3' O 0.12705(6) 1.19390(16) 0.29982(6) 0.0203(3) Uani 1 1 d . . . N1' N 0.08166(8) 0.86148(19) 0.14837(8) 0.0205(4) Uani 1 1 d . . . H1N' H 0.0815 0.9089 0.1850 0.025 Uiso 1 1 calc R . . N2' N 0.24815(7) 0.94122(18) 0.34387(7) 0.0160(3) Uani 1 1 d . . . H2N' H 0.2840 0.9498 0.3352 0.019 Uiso 1 1 calc R . . N3' N 0.07517(7) 1.07409(19) 0.35694(7) 0.0170(3) Uani 1 1 d . B . C1' C 0.02048(10) 0.8718(3) 0.08474(10) 0.0270(5) Uani 1 1 d . . . C2' C 0.14501(9) 0.7858(2) 0.16381(9) 0.0185(4) Uani 1 1 d . . . C3' C 0.20077(9) 0.7905(2) 0.23514(9) 0.0173(4) Uani 1 1 d . . . C4' C 0.26409(10) 0.7179(2) 0.25113(10) 0.0209(4) Uani 1 1 d . . . H4' H 0.3020 0.7217 0.2989 0.025 Uiso 1 1 calc R . . C5' C 0.27328(11) 0.6401(2) 0.19908(11) 0.0264(5) Uani 1 1 d . . . H5' H 0.3167 0.5903 0.2111 0.032 Uiso 1 1 calc R . . C6' C 0.21800(11) 0.6362(2) 0.12928(11) 0.0267(5) Uani 1 1 d . . . H6' H 0.2238 0.5833 0.0932 0.032 Uiso 1 1 calc R . . C7' C 0.15443(10) 0.7083(2) 0.11134(10) 0.0231(4) Uani 1 1 d . . . H7' H 0.1171 0.7051 0.0632 0.028 Uiso 1 1 calc R . . C8' C 0.19137(9) 0.8634(2) 0.29440(9) 0.0160(4) Uani 1 1 d . . . C9' C 0.25677(9) 1.0107(2) 0.40818(9) 0.0150(4) Uani 1 1 d . . . C10' C 0.20301(9) 1.0868(2) 0.41495(9) 0.0161(4) Uani 1 1 d . . . C11' C 0.21853(9) 1.1536(2) 0.48103(9) 0.0185(4) Uani 1 1 d . . . H11' H 0.1820 1.2031 0.4863 0.022 Uiso 1 1 calc R . . C12' C 0.28597(9) 1.1489(2) 0.53877(9) 0.0200(4) Uani 1 1 d . . . H12' H 0.2959 1.1949 0.5833 0.024 Uiso 1 1 calc R . . C13' C 0.33899(9) 1.0762(2) 0.53089(9) 0.0194(4) Uani 1 1 d . . . H13' H 0.3857 1.0742 0.5700 0.023 Uiso 1 1 calc R . . C14' C 0.32453(9) 1.0068(2) 0.46676(9) 0.0177(4) Uani 1 1 d . . . H14' H 0.3612 0.9557 0.4625 0.021 Uiso 1 1 calc R . . C15' C 0.13194(9) 1.1186(2) 0.35186(9) 0.0163(4) Uani 1 1 d . . . C16' C 0.00441(9) 1.0900(2) 0.29418(9) 0.0200(4) Uani 1 1 d . B . H16C H 0.0042 1.0539 0.2498 0.024 Uiso 1 1 calc R . . H16D H -0.0116 1.1987 0.2876 0.024 Uiso 1 1 calc R . . C17' C -0.04214(10) 0.9886(2) 0.31239(10) 0.0237(4) Uani 1 1 d . . . H17D H -0.0787 0.9364 0.2689 0.028 Uiso 1 1 calc R A 1 H17C H -0.0656 1.0502 0.3342 0.028 Uiso 1 1 calc R A 1 C18' C 0.00901(17) 0.8706(4) 0.36643(18) 0.0261(8) Uani 0.60 1 d P B 1 H18D H -0.0093 0.8310 0.3980 0.031 Uiso 0.60 1 calc PR B 1 H18C H 0.0168 0.7827 0.3413 0.031 Uiso 0.60 1 calc PR B 1 C18" C -0.0025(2) 0.9612(6) 0.3907(2) 0.0167(9) Uani 0.40 1 d P B 2 H18E H -0.0162 0.8616 0.4032 0.020 Uiso 0.40 1 calc PR B 2 H18F H -0.0112 1.0449 0.4172 0.020 Uiso 0.40 1 calc PR B 2 C19' C 0.07480(9) 0.9587(2) 0.40816(10) 0.0225(4) Uani 1 1 d . . . H19D H 0.1165 0.8903 0.4257 0.027 Uiso 1 1 calc R B 1 H19C H 0.0749 1.0099 0.4499 0.027 Uiso 1 1 calc R B 1 C20' C -0.03717(11) 0.9613(3) 0.08889(11) 0.0357(6) Uani 1 1 d . . . H20D H -0.0607 1.0283 0.0467 0.053 Uiso 1 1 calc R . . H20F H -0.0167 1.0244 0.1326 0.053 Uiso 1 1 calc R . . H20E H -0.0716 0.8895 0.0901 0.053 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 0.0240(7) 0.0389(9) 0.0156(7) 0.0019(6) 0.0090(6) 0.0012(6) O2 0.0162(6) 0.0245(8) 0.0160(6) -0.0006(5) 0.0088(5) -0.0012(5) O3 0.0162(6) 0.0255(8) 0.0157(6) 0.0057(5) 0.0082(5) 0.0027(5) N1 0.0172(7) 0.0250(9) 0.0140(7) 0.0006(6) 0.0081(6) 0.0029(7) N2 0.0137(7) 0.0211(9) 0.0136(7) 0.0006(6) 0.0080(6) 0.0009(6) N3 0.0136(7) 0.0227(9) 0.0122(7) 0.0026(6) 0.0063(6) 0.0016(6) C1 0.0168(9) 0.0221(11) 0.0177(9) 0.0006(8) 0.0067(8) -0.0032(8) C2 0.0172(9) 0.0176(10) 0.0174(9) 0.0027(7) 0.0099(8) -0.0016(8) C3 0.0178(9) 0.0162(10) 0.0159(9) 0.0015(7) 0.0086(7) -0.0027(8) C4 0.0159(9) 0.0219(11) 0.0165(9) 0.0034(7) 0.0072(7) 0.0006(8) C5 0.0187(9) 0.0222(11) 0.0242(10) 0.0029(8) 0.0127(8) 0.0034(8) C6 0.0251(10) 0.0201(11) 0.0214(10) -0.0028(8) 0.0151(8) -0.0016(8) C7 0.0192(9) 0.0228(11) 0.0152(9) -0.0006(8) 0.0069(8) -0.0025(8) C8 0.0150(9) 0.0189(10) 0.0130(8) 0.0043(7) 0.0056(7) 0.0028(8) C9 0.0171(9) 0.0166(10) 0.0123(8) 0.0017(7) 0.0071(7) -0.0011(7) C10 0.0154(8) 0.0173(10) 0.0142(9) 0.0015(7) 0.0080(7) -0.0017(7) C11 0.0184(9) 0.0199(10) 0.0167(9) 0.0018(7) 0.0111(8) 0.0004(8) C12 0.0200(9) 0.0244(11) 0.0135(9) -0.0005(7) 0.0085(8) -0.0032(8) C13 0.0155(9) 0.0257(11) 0.0128(9) 0.0027(7) 0.0035(7) -0.0017(8) C14 0.0151(9) 0.0205(11) 0.0186(9) 0.0037(7) 0.0082(7) 0.0025(8) C15 0.0166(9) 0.0166(10) 0.0138(9) -0.0013(7) 0.0078(7) 0.0016(7) C16 0.0131(8) 0.0273(11) 0.0156(9) 0.0021(8) 0.0053(7) 0.0030(8) C17 0.0149(9) 0.0236(11) 0.0223(10) -0.0019(8) 0.0071(8) -0.0015(8) C18 0.0196(9) 0.0238(11) 0.0226(10) 0.0007(8) 0.0091(8) -0.0017(8) C19 0.0172(9) 0.0243(11) 0.0143(9) 0.0023(7) 0.0079(7) 0.0017(8) C20 0.0227(10) 0.0373(13) 0.0214(10) 0.0098(9) 0.0102(8) 0.0096(9) O1' 0.0343(9) 0.0613(12) 0.0199(8) -0.0109(7) 0.0002(7) 0.0107(8) O2' 0.0147(6) 0.0267(8) 0.0182(6) -0.0020(5) 0.0080(5) -0.0017(6) O3' 0.0165(6) 0.0286(8) 0.0158(6) 0.0047(5) 0.0078(5) 0.0018(6) N1' 0.0183(8) 0.0283(10) 0.0133(7) -0.0014(6) 0.0062(6) -0.0003(7) N2' 0.0127(7) 0.0211(9) 0.0150(7) 0.0001(6) 0.0074(6) 0.0004(6) N3' 0.0128(7) 0.0247(9) 0.0125(7) 0.0014(6) 0.0053(6) 0.0026(6) C1' 0.0233(10) 0.0347(13) 0.0172(10) 0.0014(9) 0.0051(8) -0.0004(9) C2' 0.0192(9) 0.0184(10) 0.0192(9) 0.0014(7) 0.0102(8) -0.0034(8) C3' 0.0196(9) 0.0154(10) 0.0179(9) 0.0021(7) 0.0098(8) -0.0016(8) C4' 0.0207(9) 0.0216(11) 0.0198(9) 0.0020(8) 0.0093(8) 0.0002(8) C5' 0.0275(10) 0.0252(12) 0.0329(11) 0.0023(9) 0.0196(9) 0.0047(9) C6' 0.0377(11) 0.0251(12) 0.0268(11) -0.0048(8) 0.0232(9) -0.0037(9) C7' 0.0272(10) 0.0251(11) 0.0185(9) -0.0021(8) 0.0122(8) -0.0050(9) C8' 0.0146(8) 0.0176(10) 0.0138(9) 0.0033(7) 0.0053(7) 0.0015(7) C9' 0.0159(8) 0.0159(10) 0.0138(8) 0.0025(7) 0.0077(7) -0.0011(7) C10' 0.0147(9) 0.0176(10) 0.0166(9) 0.0023(7) 0.0081(7) -0.0012(7) C11' 0.0169(9) 0.0214(11) 0.0177(9) -0.0002(7) 0.0087(8) -0.0002(8) C12' 0.0210(9) 0.0233(11) 0.0137(9) -0.0012(7) 0.0066(8) -0.0034(8) C13' 0.0153(9) 0.0214(11) 0.0157(9) 0.0020(7) 0.0027(7) -0.0022(8) C14' 0.0155(9) 0.0185(10) 0.0184(9) 0.0037(7) 0.0076(7) 0.0017(8) C15' 0.0152(9) 0.0192(10) 0.0145(9) -0.0019(7) 0.0071(7) 0.0000(8) C16' 0.0124(8) 0.0292(11) 0.0151(9) -0.0003(8) 0.0040(7) 0.0020(8) C17' 0.0168(9) 0.0272(12) 0.0255(10) -0.0022(8) 0.0089(8) -0.0024(8) C18' 0.0247(17) 0.028(2) 0.0243(17) 0.0011(15) 0.0109(15) -0.0019(15) C18" 0.015(2) 0.019(3) 0.018(2) -0.002(2) 0.0102(19) -0.002(2) C19' 0.0183(9) 0.0302(12) 0.0213(10) 0.0066(8) 0.0114(8) 0.0020(8) C20' 0.0226(10) 0.0571(16) 0.0207(10) 0.0034(10) 0.0052(9) 0.0077(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.224(2) . ? O2 C8 1.237(2) . ? O3 C15 1.245(2) . ? N1 C1 1.367(2) . ? N1 C2 1.408(2) . ? N2 C8 1.347(2) . ? N2 C9 1.420(2) . ? N3 C15 1.334(2) . ? N3 C16 1.469(2) . ? N3 C19 1.481(2) . ? C1 C20 1.500(3) . ? C2 C7 1.395(3) . ? C2 C3 1.408(2) . ? C3 C4 1.398(2) . ? C3 C8 1.504(2) . ? C4 C5 1.387(3) . ? C5 C6 1.384(3) . ? C6 C7 1.385(3) . ? C9 C14 1.393(2) . ? C9 C10 1.402(2) . ? C10 C11 1.399(2) . ? C10 C15 1.502(2) . ? C11 C12 1.382(2) . ? C12 C13 1.388(3) . ? C13 C14 1.384(3) . ? C16 C17 1.525(3) . ? C17 C18 1.524(3) . ? C18 C19 1.530(2) . ? O1' C1' 1.220(2) . ? O2' C8' 1.234(2) . ? O3' C15' 1.242(2) . ? N1' C1' 1.365(2) . ? N1' C2' 1.407(2) . ? N2' C8' 1.351(2) . ? N2' C9' 1.419(2) . ? N3' C15' 1.339(2) . ? N3' C16' 1.474(2) . ? N3' C19' 1.480(2) . ? C1' C20' 1.506(3) . ? C2' C7' 1.396(3) . ? C2' C3' 1.411(2) . ? C3' C4' 1.392(3) . ? C3' C8' 1.506(2) . ? C4' C5' 1.387(3) . ? C5' C6' 1.386(3) . ? C6' C7' 1.386(3) . ? C9' C14' 1.393(2) . ? C9' C10' 1.402(2) . ? C10' C11' 1.400(2) . ? C10' C15' 1.500(2) . ? C11' C12' 1.382(2) . ? C12' C13' 1.386(3) . ? C13' C14' 1.379(3) . ? C16' C17' 1.519(3) . ? C17' C18" 1.476(5) . ? C17' C18' 1.538(4) . ? C18' C19' 1.476(4) . ? C18" C19' 1.528(5) . ? 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 C2 127.75(15) . . ? C8 N2 C9 126.80(14) . . ? C15 N3 C16 119.28(14) . . ? C15 N3 C19 126.09(14) . . ? C16 N3 C19 111.87(14) . . ? O1 C1 N1 123.84(17) . . ? O1 C1 C20 121.62(16) . . ? N1 C1 C20 114.54(16) . . ? C7 C2 N1 122.32(16) . . ? C7 C2 C3 119.20(17) . . ? N1 C2 C3 118.45(16) . . ? C4 C3 C2 119.12(16) . . ? C4 C3 C8 119.96(15) . . ? C2 C3 C8 120.75(16) . . ? C5 C4 C3 121.20(16) . . ? C6 C5 C4 119.13(17) . . ? C5 C6 C7 120.83(17) . . ? C6 C7 C2 120.50(16) . . ? O2 C8 N2 123.42(16) . . ? O2 C8 C3 121.26(16) . . ? N2 C8 C3 115.30(15) . . ? C14 C9 C10 119.48(16) . . ? C14 C9 N2 116.01(15) . . ? C10 C9 N2 124.49(15) . . ? C11 C10 C9 118.63(16) . . ? C11 C10 C15 117.96(16) . . ? C9 C10 C15 122.84(15) . . ? C12 C11 C10 121.30(17) . . ? C11 C12 C13 119.89(16) . . ? C14 C13 C12 119.47(16) . . ? C13 C14 C9 121.22(17) . . ? O3 C15 N3 121.44(15) . . ? O3 C15 C10 120.30(15) . . ? N3 C15 C10 118.02(15) . . ? N3 C16 C17 102.90(14) . . ? C18 C17 C16 103.46(15) . . ? C17 C18 C19 103.05(15) . . ? N3 C19 C18 103.17(14) . . ? C1' N1' C2' 129.22(16) . . ? C8' N2' C9' 127.55(15) . . ? C15' N3' C16' 119.56(14) . . ? C15' N3' C19' 125.63(15) . . ? C16' N3' C19' 110.92(14) . . ? O1' C1' N1' 123.83(19) . . ? O1' C1' C20' 121.88(17) . . ? N1' C1' C20' 114.28(17) . . ? C7' C2' N1' 122.47(16) . . ? C7' C2' C3' 119.47(17) . . ? N1' C2' C3' 118.06(16) . . ? C4' C3' C2' 118.78(17) . . ? C4' C3' C8' 119.86(15) . . ? C2' C3' C8' 121.25(16) . . ? C5' C4' C3' 121.74(17) . . ? C6' C5' C4' 118.85(19) . . ? C5' C6' C7' 120.93(18) . . ? C6' C7' C2' 120.23(17) . . ? O2' C8' N2' 123.68(16) . . ? O2' C8' C3' 121.34(16) . . ? N2' C8' C3' 114.95(15) . . ? C14' C9' C10' 119.17(16) . . ? C14' C9' N2' 116.32(15) . . ? C10' C9' N2' 124.45(15) . . ? C11' C10' C9' 119.05(16) . . ? C11' C10' C15' 117.84(16) . . ? C9' C10' C15' 122.59(15) . . ? C12' C11' C10' 121.21(17) . . ? C11' C12' C13' 119.16(17) . . ? C14' C13' C12' 120.58(16) . . ? C13' C14' C9' 120.80(17) . . ? O3' C15' N3' 122.20(16) . . ? O3' C15' C10' 120.17(15) . . ? N3' C15' C10' 117.40(15) . . ? N3' C16' C17' 104.03(14) . . ? C18" C17' C16' 106.4(2) . . ? C18" C17' C18' 40.0(2) . . ? C16' C17' C18' 104.37(18) . . ? C19' C18' C17' 104.1(2) . . ? C17' C18" C19' 104.5(3) . . ? C18' C19' N3' 104.66(18) . . ? C18' C19' C18" 40.2(2) . . ? N3' C19' C18" 101.7(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 0.1(3) . . . . ? C2 N1 C1 C20 179.83(18) . . . . ? C1 N1 C2 C7 24.4(3) . . . . ? C1 N1 C2 C3 -157.34(18) . . . . ? C7 C2 C3 C4 -0.1(3) . . . . ? N1 C2 C3 C4 -178.37(16) . . . . ? C7 C2 C3 C8 175.10(16) . . . . ? N1 C2 C3 C8 -3.2(3) . . . . ? C2 C3 C4 C5 1.1(3) . . . . ? C8 C3 C4 C5 -174.17(17) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C2 1.4(3) . . . . ? N1 C2 C7 C6 177.11(17) . . . . ? C3 C2 C7 C6 -1.1(3) . . . . ? C9 N2 C8 O2 -5.4(3) . . . . ? C9 N2 C8 C3 172.58(16) . . . . ? C4 C3 C8 O2 137.24(18) . . . . ? C2 C3 C8 O2 -37.9(3) . . . . ? C4 C3 C8 N2 -40.8(2) . . . . ? C2 C3 C8 N2 144.05(17) . . . . ? C8 N2 C9 C14 -141.14(18) . . . . ? C8 N2 C9 C10 40.8(3) . . . . ? C14 C9 C10 C11 -0.3(3) . . . . ? N2 C9 C10 C11 177.61(16) . . . . ? C14 C9 C10 C15 -171.46(17) . . . . ? N2 C9 C10 C15 6.5(3) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C15 C10 C11 C12 170.75(17) . . . . ? C10 C11 C12 C13 1.2(3) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C12 C13 C14 C9 -0.6(3) . . . . ? C10 C9 C14 C13 1.1(3) . . . . ? N2 C9 C14 C13 -177.05(17) . . . . ? C16 N3 C15 O3 -5.8(3) . . . . ? C19 N3 C15 O3 -165.37(16) . . . . ? C16 N3 C15 C10 179.87(16) . . . . ? C19 N3 C15 C10 20.3(3) . . . . ? C11 C10 C15 O3 -113.66(19) . . . . ? C9 C10 C15 O3 57.5(3) . . . . ? C11 C10 C15 N3 60.8(2) . . . . ? C9 C10 C15 N3 -128.03(19) . . . . ? C15 N3 C16 C17 -176.68(16) . . . . ? C19 N3 C16 C17 -14.3(2) . . . . ? N3 C16 C17 C18 33.14(19) . . . . ? C16 C17 C18 C19 -39.83(18) . . . . ? C15 N3 C19 C18 150.73(17) . . . . ? C16 N3 C19 C18 -10.16(19) . . . . ? C17 C18 C19 N3 30.49(18) . . . . ? C2' N1' C1' O1' -0.3(3) . . . . ? C2' N1' C1' C20' 179.18(19) . . . . ? C1' N1' C2' C7' 1.5(3) . . . . ? C1' N1' C2' C3' -178.94(19) . . . . ? C7' C2' C3' C4' 0.4(3) . . . . ? N1' C2' C3' C4' -179.21(16) . . . . ? C7' C2' C3' C8' -175.85(17) . . . . ? N1' C2' C3' C8' 4.6(3) . . . . ? C2' C3' C4' C5' -0.8(3) . . . . ? C8' C3' C4' C5' 175.49(18) . . . . ? C3' C4' C5' C6' 0.6(3) . . . . ? C4' C5' C6' C7' -0.1(3) . . . . ? C5' C6' C7' C2' -0.3(3) . . . . ? N1' C2' C7' C6' 179.73(18) . . . . ? C3' C2' C7' C6' 0.2(3) . . . . ? C9' N2' C8' O2' 3.5(3) . . . . ? C9' N2' C8' C3' -174.60(16) . . . . ? C4' C3' C8' O2' -137.11(19) . . . . ? C2' C3' C8' O2' 39.1(3) . . . . ? C4' C3' C8' N2' 41.0(2) . . . . ? C2' C3' C8' N2' -142.80(17) . . . . ? C8' N2' C9' C14' 145.23(18) . . . . ? C8' N2' C9' C10' -37.6(3) . . . . ? C14' C9' C10' C11' -1.6(3) . . . . ? N2' C9' C10' C11' -178.67(17) . . . . ? C14' C9' C10' C15' 169.94(17) . . . . ? N2' C9' C10' C15' -7.2(3) . . . . ? C9' C10' C11' C12' 1.6(3) . . . . ? C15' C10' C11' C12' -170.35(17) . . . . ? C10' C11' C12' C13' -0.2(3) . . . . ? C11' C12' C13' C14' -1.2(3) . . . . ? C12' C13' C14' C9' 1.2(3) . . . . ? C10' C9' C14' C13' 0.2(3) . . . . ? N2' C9' C14' C13' 177.54(16) . . . . ? C16' N3' C15' O3' 10.8(3) . . . . ? C19' N3' C15' O3' 166.54(17) . . . . ? C16' N3' C15' C10' -174.60(16) . . . . ? C19' N3' C15' C10' -18.9(3) . . . . ? C11' C10' C15' O3' 114.3(2) . . . . ? C9' C10' C15' O3' -57.3(3) . . . . ? C11' C10' C15' N3' -60.4(2) . . . . ? C9' C10' C15' N3' 128.02(19) . . . . ? C15' N3' C16' C17' 164.20(17) . . . . ? C19' N3' C16' C17' 5.2(2) . . . . ? N3' C16' C17' C18" 17.4(3) . . . . ? N3' C16' C17' C18' -24.1(2) . . . . ? C18" C17' C18' C19' -63.8(3) . . . . ? C16' C17' C18' C19' 34.8(3) . . . . ? C16' C17' C18" C19' -32.7(3) . . . . ? C18' C17' C18" C19' 60.2(3) . . . . ? C17' C18' C19' N3' -31.2(3) . . . . ? C17' C18' C19' C18" 59.7(3) . . . . ? C15' N3' C19' C18' -140.8(2) . . . . ? C16' N3' C19' C18' 16.7(2) . . . . ? C15' N3' C19' C18" 178.0(2) . . . . ? C16' N3' C19' C18" -24.5(3) . . . . ? C17' C18" C19' C18' -64.4(3) . . . . ? C17' C18" C19' N3' 34.5(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 C20' H20D O1' 0.98 2.68 3.413(3) 132.0 3_575 C18" H18F O1' 0.99 2.60 3.553(5) 161.9 2 C17' H17D O3' 0.99 2.48 3.371(2) 148.9 2_545 N2' H2N' O3 0.88 1.93 2.7693(19) 159.4 1_565 C20 H20C O3 0.98 2.55 3.318(2) 135.7 3_656 C19 H19B O1 0.99 2.48 3.340(2) 144.5 4_565 C18 H18B O1 0.99 2.64 3.628(2) 173.4 3_666 C13 H13 O1' 0.95 2.52 3.467(2) 174.9 3_565 N2 H2N O3' 0.88 2.02 2.8547(19) 158.3 1_545 N1' H1N' O2' 0.88 2.16 2.7956(19) 129.0 . N1 H1N O2 0.88 2.08 2.7634(19) 133.8 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.343 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.066 #===END