Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'G. Pattenden' 'Nicholas P. Mulholland' 'Iain A. S. Walters' _publ_contact_author_name 'G. Pattenden' _publ_contact_author_address ; Chemistry Department The University NOTTINGHAM NG7 2RD UNITED KINGDOM ; _publ_contact_author_email GP@NOTTINGHAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; A Concise Total Synthesis of Salinosporamide A ; data_pyrcoh _database_code_depnum_ccdc_archive 'CCDC 608046' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 N O7' _chemical_formula_sum 'C18 H23 N O7' _chemical_formula_weight 365.37 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 14.292(6) _cell_length_b 11.057(4) _cell_length_c 11.287(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.090(7) _cell_angle_gamma 90.00 _cell_volume 1782.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6831 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'trigonal prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.98 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15038 _diffrn_reflns_av_R_equivalents 0.124 _diffrn_reflns_av_sigmaI/netI 0.027 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.59 _reflns_number_total 4068 _reflns_number_gt 3308 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.36a (Bruker, 2001)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON' _refine_special_details ; ? ; _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^)+(0.064P)^2^+0.846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'NH and OH from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'N-H restrained to 0.86(1) Angstroms; OH rigid rotor; others riding' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4068 _refine_ls_number_parameters 242 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.123 _refine_ls_wR_factor_gt 0.111 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 N1 N 0.12964(8) 0.56954(11) 0.26650(11) 0.0209(3) Uani 1 1 d D . . H1N H 0.1545(13) 0.5161(14) 0.2216(15) 0.036(5) Uiso 1 1 d D . . O2 O -0.01992(7) 0.53721(9) 0.19588(10) 0.0252(2) Uani 1 1 d . . . C2 C 0.03640(10) 0.58696(12) 0.26476(13) 0.0202(3) Uani 1 1 d . . . C3 C 0.01359(9) 0.67745(12) 0.36097(13) 0.0193(3) Uani 1 1 d . . . H3 H -0.0004 0.6306 0.4340 0.023 Uiso 1 1 calc R . . O4 O 0.12403(7) 0.82716(9) 0.29145(9) 0.0224(2) Uani 1 1 d . . . H4O H 0.0898 0.8881 0.2998 0.052(7) Uiso 1 1 calc R . . C4 C 0.10815(9) 0.74281(12) 0.38401(13) 0.0189(3) Uani 1 1 d . . . C5 C 0.17922(10) 0.63719(12) 0.35876(13) 0.0196(3) Uani 1 1 d . . . C6 C -0.07234(10) 0.75329(13) 0.32800(13) 0.0219(3) Uani 1 1 d . . . H6A H -0.0547 0.8163 0.2706 0.026 Uiso 1 1 calc R . . H6B H -0.1202 0.7009 0.2885 0.026 Uiso 1 1 calc R . . C7 C -0.11445(10) 0.81361(14) 0.43425(14) 0.0251(3) Uani 1 1 d . . . H7A H -0.1310 0.7519 0.4934 0.030 Uiso 1 1 calc R . . H7B H -0.0686 0.8701 0.4720 0.030 Uiso 1 1 calc R . . O8 O -0.19682(7) 0.87847(10) 0.39428(10) 0.0270(3) Uani 1 1 d . . . C9 C -0.25339(11) 0.91438(15) 0.49167(16) 0.0301(4) Uani 1 1 d . . . H9A H -0.2910 0.9863 0.4681 0.036 Uiso 1 1 calc R . . H9B H -0.2120 0.9372 0.5603 0.036 Uiso 1 1 calc R . . C10 C -0.31801(10) 0.81439(14) 0.52788(14) 0.0244(3) Uani 1 1 d . . . C11 C -0.40259(11) 0.79434(16) 0.46540(15) 0.0309(4) Uani 1 1 d . . . H11 H -0.4208 0.8464 0.4016 0.037 Uiso 1 1 calc R . . C12 C -0.46033(11) 0.69939(17) 0.49532(16) 0.0357(4) Uani 1 1 d . . . H12 H -0.5177 0.6868 0.4520 0.043 Uiso 1 1 calc R . . C13 C -0.43499(12) 0.62297(16) 0.58776(17) 0.0351(4) Uani 1 1 d . . . H13 H -0.4744 0.5573 0.6075 0.042 Uiso 1 1 calc R . . C14 C -0.35216(12) 0.64254(15) 0.65129(16) 0.0318(4) Uani 1 1 d . . . H14 H -0.3345 0.5906 0.7153 0.038 Uiso 1 1 calc R . . C15 C -0.29458(11) 0.73811(15) 0.62159(14) 0.0273(3) Uani 1 1 d . . . H15 H -0.2380 0.7514 0.6665 0.033 Uiso 1 1 calc R . . C41 C 0.12204(10) 0.79927(13) 0.50501(14) 0.0238(3) Uani 1 1 d . . . H41A H 0.0757 0.8635 0.5146 0.036 Uiso 1 1 calc R . . H41B H 0.1852 0.8335 0.5130 0.036 Uiso 1 1 calc R . . H41C H 0.1142 0.7374 0.5661 0.036 Uiso 1 1 calc R . . O51 O 0.13557(8) 0.48015(11) 0.49346(11) 0.0349(3) Uani 1 1 d . . . C51 C 0.19210(10) 0.55581(13) 0.46987(13) 0.0228(3) Uani 1 1 d . . . O52 O 0.26957(8) 0.57833(10) 0.53378(10) 0.0278(3) Uani 1 1 d . . . C52 C 0.28219(13) 0.50373(16) 0.63933(15) 0.0332(4) Uani 1 1 d . . . H52A H 0.3406 0.5263 0.6817 0.050 Uiso 1 1 calc R . . H52B H 0.2850 0.4184 0.6163 0.050 Uiso 1 1 calc R . . H52C H 0.2295 0.5162 0.6911 0.050 Uiso 1 1 calc R . . O53 O 0.31636(7) 0.76528(10) 0.37311(10) 0.0294(3) Uani 1 1 d . . . C53 C 0.27274(10) 0.68893(13) 0.32034(13) 0.0212(3) Uani 1 1 d . . . O54 O 0.29978(7) 0.63524(10) 0.22087(10) 0.0270(3) Uani 1 1 d . . . C54 C 0.38659(11) 0.67882(17) 0.17330(16) 0.0334(4) Uani 1 1 d . . . H54A H 0.3999 0.6338 0.1011 0.050 Uiso 1 1 calc R . . H54B H 0.4379 0.6670 0.2322 0.050 Uiso 1 1 calc R . . H54C H 0.3806 0.7651 0.1546 0.050 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 N1 0.0173(6) 0.0191(6) 0.0265(6) -0.0042(5) 0.0023(5) -0.0008(4) O2 0.0215(5) 0.0231(5) 0.0307(6) -0.0023(4) -0.0020(4) -0.0041(4) C2 0.0187(7) 0.0174(6) 0.0247(7) 0.0030(5) 0.0017(5) -0.0027(5) C3 0.0149(6) 0.0185(6) 0.0244(7) 0.0004(5) 0.0008(5) -0.0014(5) O4 0.0208(5) 0.0180(5) 0.0284(6) 0.0044(4) 0.0035(4) 0.0009(4) C4 0.0158(6) 0.0170(6) 0.0240(7) 0.0019(5) 0.0017(5) -0.0002(5) C5 0.0160(6) 0.0173(6) 0.0255(7) -0.0007(5) 0.0012(5) -0.0009(5) C6 0.0164(6) 0.0220(7) 0.0272(8) 0.0020(6) 0.0002(5) 0.0000(5) C7 0.0193(7) 0.0257(7) 0.0304(8) 0.0025(6) 0.0022(6) 0.0038(6) O8 0.0186(5) 0.0278(5) 0.0350(6) 0.0065(5) 0.0073(4) 0.0053(4) C9 0.0258(8) 0.0249(8) 0.0404(9) 0.0011(7) 0.0124(7) 0.0040(6) C10 0.0191(7) 0.0258(7) 0.0288(8) -0.0002(6) 0.0074(6) 0.0038(6) C11 0.0215(7) 0.0415(9) 0.0299(8) 0.0044(7) 0.0025(6) 0.0083(7) C12 0.0177(7) 0.0500(11) 0.0393(10) -0.0092(8) 0.0015(6) -0.0021(7) C13 0.0305(9) 0.0321(9) 0.0437(10) -0.0047(7) 0.0156(7) -0.0051(7) C14 0.0329(9) 0.0307(8) 0.0323(9) 0.0051(7) 0.0093(7) 0.0056(7) C15 0.0202(7) 0.0336(8) 0.0281(8) 0.0000(6) 0.0009(6) 0.0030(6) C41 0.0202(7) 0.0226(7) 0.0286(8) -0.0031(6) -0.0001(6) 0.0006(5) O51 0.0258(6) 0.0328(6) 0.0460(7) 0.0171(5) 0.0011(5) -0.0044(5) C51 0.0206(7) 0.0203(7) 0.0278(8) 0.0013(6) 0.0040(6) 0.0039(5) O52 0.0262(6) 0.0282(6) 0.0288(6) 0.0043(5) -0.0029(4) 0.0003(4) C52 0.0362(9) 0.0342(9) 0.0288(8) 0.0073(7) -0.0026(7) 0.0071(7) O53 0.0202(5) 0.0313(6) 0.0367(6) -0.0033(5) 0.0006(4) -0.0060(4) C53 0.0165(6) 0.0202(7) 0.0268(7) 0.0044(6) 0.0004(5) 0.0011(5) O54 0.0202(5) 0.0307(6) 0.0305(6) -0.0015(5) 0.0074(4) -0.0049(4) C54 0.0209(8) 0.0414(9) 0.0385(9) 0.0018(7) 0.0105(6) -0.0052(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 C2 1.3459(19) . ? N1 C5 1.4465(19) . ? N1 H1N 0.86(1) . ? O2 C2 1.2286(18) . ? C2 C3 1.521(2) . ? C3 C6 1.522(2) . ? C3 C4 1.5462(19) . ? C3 H3 1.0000 . ? O4 C4 1.4248(17) . ? O4 H4O 0.8400 . ? C4 C41 1.508(2) . ? C4 C5 1.5805(19) . ? C5 C53 1.531(2) . ? C5 C51 1.549(2) . ? C6 C7 1.516(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O8 1.4370(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? O8 C9 1.4438(19) . ? C9 C10 1.507(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C15 1.384(2) . ? C10 C11 1.395(2) . ? C11 C12 1.385(3) . ? C11 H11 0.9500 . ? C12 C13 1.381(3) . ? C12 H12 0.9500 . ? C13 C14 1.379(3) . ? C13 H13 0.9500 . ? C14 C15 1.388(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? O51 C51 1.1997(19) . ? C51 O52 1.3228(19) . ? O52 C52 1.455(2) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? O53 C53 1.1954(18) . ? C53 O54 1.3394(19) . ? O54 C54 1.4519(19) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 113.28(12) . . ? C2 N1 H1N 121.1(14) . . ? C5 N1 H1N 125.2(14) . . ? O2 C2 N1 124.80(14) . . ? O2 C2 C3 126.44(13) . . ? N1 C2 C3 108.77(12) . . ? C2 C3 C6 112.33(12) . . ? C2 C3 C4 102.64(11) . . ? C6 C3 C4 118.44(12) . . ? C2 C3 H3 107.6 . . ? C6 C3 H3 107.6 . . ? C4 C3 H3 107.6 . . ? C4 O4 H4O 109.5 . . ? O4 C4 C41 111.95(12) . . ? O4 C4 C3 110.14(11) . . ? C41 C4 C3 115.54(12) . . ? O4 C4 C5 103.34(11) . . ? C41 C4 C5 113.89(12) . . ? C3 C4 C5 100.83(11) . . ? N1 C5 C53 113.52(12) . . ? N1 C5 C51 108.85(12) . . ? C53 C5 C51 111.54(12) . . ? N1 C5 C4 102.16(11) . . ? C53 C5 C4 110.39(11) . . ? C51 C5 C4 109.96(11) . . ? C7 C6 C3 112.89(12) . . ? C7 C6 H6A 109.0 . . ? C3 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C3 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O8 C7 C6 108.39(13) . . ? O8 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? O8 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C7 O8 C9 111.92(12) . . ? O8 C9 C10 111.75(13) . . ? O8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? O8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C15 C10 C11 118.06(15) . . ? C15 C10 C9 121.39(15) . . ? C11 C10 C9 120.53(15) . . ? C12 C11 C10 120.69(16) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.40(16) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 119.58(16) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 119.96(16) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C10 C15 C14 121.30(15) . . ? C10 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C4 C41 H41A 109.5 . . ? C4 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C4 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O51 C51 O52 124.56(14) . . ? O51 C51 C5 121.58(14) . . ? O52 C51 C5 113.86(12) . . ? C51 O52 C52 114.60(12) . . ? O52 C52 H52A 109.5 . . ? O52 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O52 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O53 C53 O54 124.72(13) . . ? O53 C53 C5 124.58(14) . . ? O54 C53 C5 110.69(12) . . ? C53 O54 C54 116.07(12) . . ? O54 C54 H54A 109.5 . . ? O54 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? O54 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 O2 -178.47(13) . . . . ? C5 N1 C2 C3 1.64(16) . . . . ? O2 C2 C3 C6 -31.0(2) . . . . ? N1 C2 C3 C6 148.89(12) . . . . ? O2 C2 C3 C4 -159.29(14) . . . . ? N1 C2 C3 C4 20.60(14) . . . . ? C2 C3 C4 O4 76.60(13) . . . . ? C6 C3 C4 O4 -47.75(16) . . . . ? C2 C3 C4 C41 -155.34(12) . . . . ? C6 C3 C4 C41 80.31(16) . . . . ? C2 C3 C4 C5 -32.09(13) . . . . ? C6 C3 C4 C5 -156.43(12) . . . . ? C2 N1 C5 C53 -141.46(12) . . . . ? C2 N1 C5 C51 93.66(14) . . . . ? C2 N1 C5 C4 -22.61(15) . . . . ? O4 C4 C5 N1 -80.86(12) . . . . ? C41 C4 C5 N1 157.46(12) . . . . ? C3 C4 C5 N1 33.07(13) . . . . ? O4 C4 C5 C53 40.19(14) . . . . ? C41 C4 C5 C53 -81.50(15) . . . . ? C3 C4 C5 C53 154.11(12) . . . . ? O4 C4 C5 C51 163.68(11) . . . . ? C41 C4 C5 C51 41.99(16) . . . . ? C3 C4 C5 C51 -82.40(13) . . . . ? C2 C3 C6 C7 161.54(12) . . . . ? C4 C3 C6 C7 -79.03(16) . . . . ? C3 C6 C7 O8 -177.68(11) . . . . ? C6 C7 O8 C9 166.24(12) . . . . ? C7 O8 C9 C10 -84.24(16) . . . . ? O8 C9 C10 C15 96.85(18) . . . . ? O8 C9 C10 C11 -81.54(18) . . . . ? C15 C10 C11 C12 -1.1(2) . . . . ? C9 C10 C11 C12 177.29(15) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C11 C10 C15 C14 1.5(2) . . . . ? C9 C10 C15 C14 -176.94(15) . . . . ? C13 C14 C15 C10 -0.7(2) . . . . ? N1 C5 C51 O51 -31.66(19) . . . . ? C53 C5 C51 O51 -157.69(14) . . . . ? C4 C5 C51 O51 79.50(17) . . . . ? N1 C5 C51 O52 148.45(12) . . . . ? C53 C5 C51 O52 22.42(17) . . . . ? C4 C5 C51 O52 -100.40(14) . . . . ? O51 C51 O52 C52 -0.6(2) . . . . ? C5 C51 O52 C52 179.25(12) . . . . ? N1 C5 C53 O53 165.31(14) . . . . ? C51 C5 C53 O53 -71.27(18) . . . . ? C4 C5 C53 O53 51.30(19) . . . . ? N1 C5 C53 O54 -15.89(16) . . . . ? C51 C5 C53 O54 107.53(14) . . . . ? C4 C5 C53 O54 -129.90(12) . . . . ? O53 C53 O54 C54 -2.8(2) . . . . ? C5 C53 O54 C54 178.38(12) . . . . ? 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 O8 0.863(9) 2.109(10) 2.9674(18) 172(2) 2_545 O4 H4O O2 0.84 1.93 2.7648(16) 173 2 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.33 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.07 #===END of CIF