# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Stefan Brase' _publ_contact_author_email BRAESE@KIT.EDU _publ_section_title ; Towards an asymmetric synthesis of the bacterial peptide deformylase (PDF) inhibitor Fumimycin ; loop_ _publ_author_name 'Stefan Brase' 'Patrick J. Grob' 'Caroline E. Hartmann' 'Martin Nieger' data_sb106_hy _database_code_depnum_ccdc_archive 'CCDC 738983' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Diethyl-1-(2-(5-(alloyoxy)-2,4-dimethoxyphenyl)-1-oxopropan-2-yl)hydrazine- 1,2-dicarboxylate ; _chemical_name_common ; Diethyl-1-(2-(5-(alloyoxy)-2,4-dimethoxyphenyl)-1-oxopropan-2- yl)hydrazine-1,2-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 N2 O8' _chemical_formula_sum 'C20 H28 N2 O8' _chemical_formula_weight 424.44 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 'P 21 21 21' 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 8.681(1) _cell_length_b 9.784(1) _cell_length_c 24.875(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2112.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 152 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 47 mm, 90 sec./deg., 1 deg., 2 sets, 400 frames, ; _diffrn_ambient_temperature 123(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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16621 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4774 _reflns_number_gt 4376 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The absolute configuration cannot be determined reliably, but using Bayesian statistics on Bijvoet differences (C2:S): FLEQ = 0.05(40) (R.W.W. Hooft et al., J. Appl. Cryst. 2008, 41, 96-103). ; _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^)+(0.0375P)^2^+0.4191P] 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(7) _refine_ls_number_reflns 4774 _refine_ls_number_parameters 276 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.072 _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 0.59173(14) -0.13625(12) 0.60706(5) 0.0259(3) Uani 1 1 d . . . C1 C 0.56992(18) -0.06523(15) 0.64574(6) 0.0185(3) Uani 1 1 d . . . H1 H 0.6014 -0.0957 0.6803 0.022 Uiso 1 1 calc R . . C2 C 0.49147(17) 0.07438(15) 0.63961(6) 0.0143(3) Uani 1 1 d . . . C21 C 0.34900(19) 0.05422(16) 0.60414(6) 0.0188(3) Uani 1 1 d . . . H21A H 0.2788 -0.0108 0.6214 0.028 Uiso 1 1 calc R . . H21B H 0.3806 0.0185 0.5690 0.028 Uiso 1 1 calc R . . H21C H 0.2965 0.1420 0.5993 0.028 Uiso 1 1 calc R . . N3 N 0.44721(15) 0.12459(12) 0.69425(5) 0.0138(3) Uani 1 1 d . . . C31 C 0.35943(17) 0.04472(15) 0.72737(6) 0.0148(3) Uani 1 1 d . . . O31 O 0.33482(13) -0.07551(11) 0.71878(4) 0.0179(2) Uani 1 1 d . . . O32 O 0.30744(13) 0.11472(11) 0.76959(4) 0.0184(2) Uani 1 1 d . . . C32 C 0.2226(2) 0.03598(16) 0.80934(6) 0.0208(3) Uani 1 1 d . . . H32A H 0.2940 -0.0196 0.8314 0.025 Uiso 1 1 calc R . . H32B H 0.1481 -0.0259 0.7915 0.025 Uiso 1 1 calc R . . C33 C 0.1398(2) 0.13834(18) 0.84381(6) 0.0243(4) Uani 1 1 d . . . H33A H 0.0806 0.0903 0.8715 0.037 Uiso 1 1 calc R . . H33B H 0.0698 0.1925 0.8214 0.037 Uiso 1 1 calc R . . H33C H 0.2150 0.1990 0.8610 0.037 Uiso 1 1 calc R . . N4 N 0.45820(15) 0.26288(12) 0.70501(5) 0.0140(3) Uani 1 1 d D . . H4 H 0.5357(18) 0.2899(18) 0.7247(7) 0.017 Uiso 1 1 d D . . C41 C 0.33847(18) 0.34688(14) 0.69333(6) 0.0152(3) Uani 1 1 d . . . O41 O 0.22114(13) 0.31424(11) 0.67048(5) 0.0218(2) Uani 1 1 d . . . O42 O 0.37237(14) 0.47275(11) 0.71113(5) 0.0219(3) Uani 1 1 d . . . C42 C 0.2699(2) 0.58081(16) 0.69289(7) 0.0257(4) Uani 1 1 d . . . H42A H 0.2684 0.6557 0.7196 0.031 Uiso 1 1 calc R . . H42B H 0.1638 0.5447 0.6894 0.031 Uiso 1 1 calc R . . C43 C 0.3235(3) 0.63460(19) 0.63982(9) 0.0368(5) Uani 1 1 d . . . H43A H 0.2538 0.7071 0.6277 0.055 Uiso 1 1 calc R . . H43B H 0.3240 0.5604 0.6134 0.055 Uiso 1 1 calc R . . H43C H 0.4279 0.6715 0.6436 0.055 Uiso 1 1 calc R . . C1' C 0.60742(17) 0.17415(15) 0.61519(6) 0.0141(3) Uani 1 1 d . . . C2' C 0.76129(17) 0.17348(15) 0.63120(6) 0.0155(3) Uani 1 1 d . . . O2' O 0.79613(12) 0.08720(11) 0.67289(5) 0.0204(2) Uani 1 1 d . . . C21' C 0.9537(2) 0.0532(2) 0.68171(8) 0.0301(4) Uani 1 1 d . . . H21D H 1.0000 0.0224 0.6479 0.045 Uiso 1 1 calc R . . H21E H 0.9605 -0.0202 0.7084 0.045 Uiso 1 1 calc R . . H21F H 1.0090 0.1338 0.6949 0.045 Uiso 1 1 calc R . . C3' C 0.87100(18) 0.25577(15) 0.60668(6) 0.0162(3) Uani 1 1 d . . . H3' H 0.9755 0.2523 0.6179 0.019 Uiso 1 1 calc R . . C4' C 0.82588(18) 0.34366(15) 0.56535(6) 0.0161(3) Uani 1 1 d . . . O4' O 0.92550(13) 0.42461(11) 0.53732(4) 0.0200(2) Uani 1 1 d . . . C41' C 1.08577(19) 0.40617(19) 0.54688(7) 0.0237(3) Uani 1 1 d . . . H41A H 1.1094 0.4297 0.5843 0.036 Uiso 1 1 calc R . . H41B H 1.1448 0.4656 0.5227 0.036 Uiso 1 1 calc R . . H41C H 1.1135 0.3106 0.5402 0.036 Uiso 1 1 calc R . . C5' C 0.67122(19) 0.35219(15) 0.55128(6) 0.0160(3) Uani 1 1 d . . . O5' O 0.62146(13) 0.43671(11) 0.51033(4) 0.0191(2) Uani 1 1 d . . . C51' C 0.6401(2) 0.58019(16) 0.52047(7) 0.0252(4) Uani 1 1 d . . . H51A H 0.7436 0.6101 0.5085 0.030 Uiso 1 1 calc R . . H51B H 0.6310 0.5984 0.5595 0.030 Uiso 1 1 calc R . . C52' C 0.5201(2) 0.65717(18) 0.49091(7) 0.0311(4) Uani 1 1 d . . . H52' H 0.5242 0.7541 0.4929 0.037 Uiso 1 1 calc R . . C53' C 0.4092(2) 0.6037(2) 0.46241(8) 0.0388(5) Uani 1 1 d . . . H53A H 0.4006 0.5072 0.4593 0.047 Uiso 1 1 calc R . . H53B H 0.3370 0.6613 0.4447 0.047 Uiso 1 1 calc R . . C6' C 0.56509(18) 0.26744(15) 0.57530(6) 0.0152(3) Uani 1 1 d . . . H6' H 0.4603 0.2725 0.5645 0.018 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 0.0288(7) 0.0198(5) 0.0292(6) -0.0066(5) 0.0046(5) -0.0001(5) C1 0.0167(8) 0.0152(7) 0.0235(7) 0.0010(6) 0.0022(6) -0.0041(6) C2 0.0146(8) 0.0157(7) 0.0125(6) -0.0007(5) 0.0014(5) -0.0010(6) C21 0.0187(8) 0.0214(7) 0.0163(7) -0.0005(6) -0.0007(6) -0.0043(6) N3 0.0175(7) 0.0112(5) 0.0127(5) -0.0005(4) 0.0012(5) -0.0001(5) C31 0.0132(8) 0.0173(7) 0.0140(6) 0.0024(5) -0.0025(6) 0.0012(6) O31 0.0202(6) 0.0143(5) 0.0192(5) 0.0010(4) -0.0013(4) -0.0029(4) O32 0.0230(6) 0.0178(5) 0.0143(5) 0.0021(4) 0.0048(4) -0.0025(5) C32 0.0238(9) 0.0216(7) 0.0171(7) 0.0055(6) 0.0045(6) -0.0044(6) C33 0.0256(9) 0.0266(8) 0.0209(7) -0.0019(6) 0.0075(6) -0.0050(7) N4 0.0148(7) 0.0110(5) 0.0162(6) -0.0018(4) -0.0018(5) -0.0008(5) C41 0.0172(8) 0.0154(7) 0.0130(6) 0.0006(5) 0.0004(6) -0.0024(6) O41 0.0189(6) 0.0181(5) 0.0285(6) -0.0003(5) -0.0079(5) 0.0003(5) O42 0.0252(7) 0.0134(5) 0.0272(6) -0.0040(4) -0.0090(5) 0.0036(5) C42 0.0275(9) 0.0149(7) 0.0345(9) -0.0014(7) -0.0080(7) 0.0061(7) C43 0.0450(12) 0.0225(8) 0.0430(11) 0.0077(8) -0.0092(9) -0.0091(8) C1' 0.0149(7) 0.0135(6) 0.0138(6) -0.0010(5) 0.0007(5) -0.0012(6) C2' 0.0181(8) 0.0156(6) 0.0128(6) 0.0012(5) -0.0010(6) 0.0007(6) O2' 0.0149(6) 0.0250(6) 0.0213(5) 0.0088(5) -0.0037(4) -0.0009(5) C21' 0.0188(9) 0.0364(10) 0.0351(10) 0.0148(7) -0.0067(7) 0.0012(7) C3' 0.0149(8) 0.0173(7) 0.0165(7) -0.0002(5) -0.0022(6) -0.0009(6) C4' 0.0193(8) 0.0150(7) 0.0138(6) 0.0000(5) 0.0023(6) -0.0017(6) O4' 0.0168(6) 0.0240(6) 0.0191(5) 0.0056(4) 0.0019(4) -0.0036(5) C41' 0.0168(8) 0.0329(9) 0.0214(7) 0.0039(7) 0.0023(6) -0.0047(7) C5' 0.0204(8) 0.0157(7) 0.0119(6) 0.0003(5) -0.0021(6) 0.0006(6) O5' 0.0261(6) 0.0156(5) 0.0157(5) 0.0044(4) -0.0053(4) -0.0021(4) C51' 0.0297(10) 0.0171(7) 0.0288(8) 0.0027(6) -0.0063(7) -0.0033(7) C52' 0.0393(11) 0.0218(8) 0.0321(9) 0.0042(7) -0.0072(8) 0.0039(8) C53' 0.0446(13) 0.0332(10) 0.0384(11) 0.0011(8) -0.0175(9) 0.0107(9) C6' 0.0154(8) 0.0155(7) 0.0148(7) -0.0004(5) -0.0020(6) 0.0009(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.202(2) . ? C1 C2 1.534(2) . ? C1 H1 0.9500 . ? C2 N3 1.4954(17) . ? C2 C1' 1.528(2) . ? C2 C21 1.532(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N3 C31 1.3676(19) . ? N3 N4 1.3825(17) . ? C31 O31 1.2145(18) . ? C31 O32 1.3326(18) . ? O32 C32 1.4537(18) . ? C32 C33 1.502(2) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? N4 C41 1.357(2) . ? N4 H4 0.873(14) . ? C41 O41 1.2093(19) . ? C41 O42 1.3415(18) . ? O42 C42 1.4544(19) . ? C42 C43 1.496(3) . ? C42 H42A 0.9900 . ? C42 H42B 0.9900 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C1' C2' 1.394(2) . ? C1' C6' 1.397(2) . ? C2' O2' 1.3710(17) . ? C2' C3' 1.388(2) . ? O2' C21' 1.425(2) . ? C21' H21D 0.9800 . ? C21' H21E 0.9800 . ? C21' H21F 0.9800 . ? C3' C4' 1.396(2) . ? C3' H3' 0.9500 . ? C4' O4' 1.3642(18) . ? C4' C5' 1.390(2) . ? O4' C41' 1.423(2) . ? C41' H41A 0.9800 . ? C41' H41B 0.9800 . ? C41' H41C 0.9800 . ? C5' C6' 1.376(2) . ? C5' O5' 1.3813(17) . ? O5' C51' 1.4355(19) . ? C51' C52' 1.481(2) . ? C51' H51A 0.9900 . ? C51' H51B 0.9900 . ? C52' C53' 1.305(3) . ? C52' H52' 0.9500 . ? C53' H53A 0.9500 . ? C53' H53B 0.9500 . ? C6' H6' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 120.35(14) . . ? O1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? N3 C2 C1' 108.71(11) . . ? N3 C2 C21 111.00(12) . . ? C1' C2 C21 112.64(12) . . ? N3 C2 C1 108.44(12) . . ? C1' C2 C1 108.42(12) . . ? C21 C2 C1 107.52(12) . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C31 N3 N4 118.76(12) . . ? C31 N3 C2 120.20(12) . . ? N4 N3 C2 118.67(11) . . ? O31 C31 O32 125.23(14) . . ? O31 C31 N3 123.06(14) . . ? O32 C31 N3 111.70(12) . . ? C31 O32 C32 115.80(11) . . ? O32 C32 C33 106.11(12) . . ? O32 C32 H32A 110.5 . . ? C33 C32 H32A 110.5 . . ? O32 C32 H32B 110.5 . . ? C33 C32 H32B 110.5 . . ? H32A C32 H32B 108.7 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C41 N4 N3 119.90(12) . . ? C41 N4 H4 121.8(12) . . ? N3 N4 H4 117.3(12) . . ? O41 C41 O42 125.62(14) . . ? O41 C41 N4 125.88(14) . . ? O42 C41 N4 108.50(12) . . ? C41 O42 C42 115.48(12) . . ? O42 C42 C43 109.92(15) . . ? O42 C42 H42A 109.7 . . ? C43 C42 H42A 109.7 . . ? O42 C42 H42B 109.7 . . ? C43 C42 H42B 109.7 . . ? H42A C42 H42B 108.2 . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C2' C1' C6' 117.26(13) . . ? C2' C1' C2 120.97(13) . . ? C6' C1' C2 121.77(13) . . ? O2' C2' C3' 122.55(13) . . ? O2' C2' C1' 115.50(13) . . ? C3' C2' C1' 121.95(13) . . ? C2' O2' C21' 118.17(12) . . ? O2' C21' H21D 109.5 . . ? O2' C21' H21E 109.5 . . ? H21D C21' H21E 109.5 . . ? O2' C21' H21F 109.5 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 109.5 . . ? C2' C3' C4' 119.22(14) . . ? C2' C3' H3' 120.4 . . ? C4' C3' H3' 120.4 . . ? O4' C4' C5' 116.66(13) . . ? O4' C4' C3' 123.78(14) . . ? C5' C4' C3' 119.56(14) . . ? C4' O4' C41' 117.44(12) . . ? O4' C41' H41A 109.5 . . ? O4' C41' H41B 109.5 . . ? H41A C41' H41B 109.5 . . ? O4' C41' H41C 109.5 . . ? H41A C41' H41C 109.5 . . ? H41B C41' H41C 109.5 . . ? C6' C5' O5' 118.13(14) . . ? C6' C5' C4' 120.08(13) . . ? O5' C5' C4' 121.59(13) . . ? C5' O5' C51' 114.87(12) . . ? O5' C51' C52' 109.31(14) . . ? O5' C51' H51A 109.8 . . ? C52' C51' H51A 109.8 . . ? O5' C51' H51B 109.8 . . ? C52' C51' H51B 109.8 . . ? H51A C51' H51B 108.3 . . ? C53' C52' C51' 125.79(17) . . ? C53' C52' H52' 117.1 . . ? C51' C52' H52' 117.1 . . ? C52' C53' H53A 120.0 . . ? C52' C53' H53B 120.0 . . ? H53A C53' H53B 120.0 . . ? C5' C6' C1' 121.73(14) . . ? C5' C6' H6' 119.1 . . ? C1' C6' H6' 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N3 167.16(14) . . . . ? O1 C1 C2 C1' -74.97(18) . . . . ? O1 C1 C2 C21 47.07(19) . . . . ? C1' C2 N3 C31 -171.81(13) . . . . ? C21 C2 N3 C31 63.77(16) . . . . ? C1 C2 N3 C31 -54.13(17) . . . . ? C1' C2 N3 N4 25.91(17) . . . . ? C21 C2 N3 N4 -98.51(15) . . . . ? C1 C2 N3 N4 143.59(13) . . . . ? N4 N3 C31 O31 174.74(13) . . . . ? C2 N3 C31 O31 12.5(2) . . . . ? N4 N3 C31 O32 -5.97(19) . . . . ? C2 N3 C31 O32 -168.24(12) . . . . ? O31 C31 O32 C32 3.8(2) . . . . ? N3 C31 O32 C32 -175.47(12) . . . . ? C31 O32 C32 C33 -164.67(13) . . . . ? C31 N3 N4 C41 -75.41(17) . . . . ? C2 N3 N4 C41 87.14(16) . . . . ? N3 N4 C41 O41 -5.0(2) . . . . ? N3 N4 C41 O42 175.32(12) . . . . ? O41 C41 O42 C42 -11.0(2) . . . . ? N4 C41 O42 C42 168.69(13) . . . . ? C41 O42 C42 C43 -86.85(17) . . . . ? N3 C2 C1' C2' 77.42(16) . . . . ? C21 C2 C1' C2' -159.14(13) . . . . ? C1 C2 C1' C2' -40.28(18) . . . . ? N3 C2 C1' C6' -103.96(15) . . . . ? C21 C2 C1' C6' 19.48(19) . . . . ? C1 C2 C1' C6' 138.34(14) . . . . ? C6' C1' C2' O2' 175.75(13) . . . . ? C2 C1' C2' O2' -5.6(2) . . . . ? C6' C1' C2' C3' -3.7(2) . . . . ? C2 C1' C2' C3' 174.94(13) . . . . ? C3' C2' O2' C21' -17.3(2) . . . . ? C1' C2' O2' C21' 163.23(14) . . . . ? O2' C2' C3' C4' -178.34(13) . . . . ? C1' C2' C3' C4' 1.1(2) . . . . ? C2' C3' C4' O4' -177.36(13) . . . . ? C2' C3' C4' C5' 3.1(2) . . . . ? C5' C4' O4' C41' -173.06(14) . . . . ? C3' C4' O4' C41' 7.4(2) . . . . ? O4' C4' C5' C6' 175.83(13) . . . . ? C3' C4' C5' C6' -4.6(2) . . . . ? O4' C4' C5' O5' 1.1(2) . . . . ? C3' C4' C5' O5' -179.37(13) . . . . ? C6' C5' O5' C51' 119.19(15) . . . . ? C4' C5' O5' C51' -65.96(19) . . . . ? C5' O5' C51' C52' -151.37(14) . . . . ? O5' C51' C52' C53' 3.5(3) . . . . ? O5' C5' C6' C1' 176.84(13) . . . . ? C4' C5' C6' C1' 1.9(2) . . . . ? C2' C1' C6' C5' 2.2(2) . . . . ? C2 C1' C6' C5' -176.45(13) . . . . ? 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 N4 H4 O31 0.873(14) 2.231(15) 3.0532(17) 157.0(16) 3_656 C3' H3' O41 0.95 2.57 3.476(2) 158.8 1_655 C33 H33C O1 0.98 2.46 3.433(2) 172.9 3_656 C43 H43C O1 0.98 2.53 3.333(2) 139.5 1_565 C53' H53B O1 0.95 2.50 3.268(2) 137.9 4_456 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.212 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.048 #============================================================================== #_eof # End of Crystallographic Information File