# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Neil Thomas' 'Gurdyal Singh Besra' 'Alexander J. Blake' 'Sylvaine Cren' 'Sudagar S. Gurcha' _publ_contact_author_name 'Neil Thomas' _publ_contact_author_address ; Centre for Biomolecular Sciences University of Nottingham School of Chemistry University Park Nottingham Notts NG7 2RD UNITED KINGDOM ; _publ_contact_author_email NEIL.THOMAS@NOTTINGHAM.AC.UK _publ_section_title ; Synthesis and biological evaluation of new inhibitors of UDP-alpha-D-Galf transferase - a key enzyme in M. tuberculosis cell wall biosynthesis ; data_IPOSNO _database_code_depnum_ccdc_archive 'CCDC 241487' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H25 N O5' _chemical_formula_sum 'C14 H25 N O5' _chemical_formula_weight 287.35 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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.668(2) _cell_length_b 5.7076(8) _cell_length_c 18.373(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.266(3) _cell_angle_gamma 90.00 _cell_volume 1531.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4595 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.45 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.094 _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 'normal-focus 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 . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 9434 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.023 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3464 _reflns_number_gt 2821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2003)' _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^)+(0.058P)^2^+0.37P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'OH from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotating group; riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3464 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.113 _refine_ls_wR_factor_gt 0.107 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _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 0.68189(7) 0.25006(19) 0.64351(6) 0.0246(2) Uani 1 1 d . . . C2 C 0.72899(9) 0.4482(2) 0.68068(7) 0.0254(3) Uani 1 1 d . . . H2A H 0.7510 0.4079 0.7317 0.030 Uiso 1 1 calc R . . H2B H 0.6885 0.5869 0.6808 0.030 Uiso 1 1 calc R . . C3 C 0.80882(9) 0.4916(2) 0.63474(7) 0.0273(3) Uani 1 1 d . . . H3 H 0.8611 0.3873 0.6521 0.033 Uiso 1 1 calc R . . C4 C 0.77134(8) 0.4182(2) 0.55861(7) 0.0249(3) Uani 1 1 d . . . H4 H 0.7270 0.5404 0.5387 0.030 Uiso 1 1 calc R . . C5 C 0.71782(9) 0.1969(2) 0.57312(7) 0.0242(3) Uani 1 1 d . . . H5A H 0.6676 0.1702 0.5342 0.029 Uiso 1 1 calc R . . H5B H 0.7582 0.0577 0.5770 0.029 Uiso 1 1 calc R . . O6 O 0.83871(6) 0.72743(16) 0.63626(5) 0.0288(2) Uani 1 1 d . . . H6O H 0.8689 0.7551 0.6764 0.043 Uiso 1 1 calc R . . C7 C 0.84180(9) 0.3857(3) 0.50564(7) 0.0303(3) Uani 1 1 d . . . H7 H 0.8906 0.2769 0.5270 0.036 Uiso 1 1 calc R . . C8 C 0.88562(9) 0.6069(3) 0.47928(7) 0.0310(3) Uani 1 1 d . . . H8A H 0.8405 0.7356 0.4717 0.037 Uiso 1 1 calc R . . H8B H 0.9372 0.6589 0.5140 0.037 Uiso 1 1 calc R . . O9 O 0.91677(6) 0.53169(18) 0.41167(5) 0.0333(2) Uani 1 1 d . . . O10 O 0.80015(7) 0.28994(18) 0.43896(5) 0.0327(2) Uani 1 1 d . . . C10 C 0.85244(9) 0.3632(3) 0.38088(7) 0.0291(3) Uani 1 1 d . . . C11 C 0.90466(11) 0.1602(3) 0.35333(9) 0.0409(4) Uani 1 1 d . . . H11A H 0.9456 0.0954 0.3935 0.061 Uiso 1 1 calc R . . H11B H 0.9409 0.2137 0.3143 0.061 Uiso 1 1 calc R . . H11C H 0.8616 0.0389 0.3343 0.061 Uiso 1 1 calc R . . C12 C 0.78721(10) 0.4754(3) 0.32261(9) 0.0421(4) Uani 1 1 d . . . H12A H 0.7555 0.6062 0.3439 0.063 Uiso 1 1 calc R . . H12B H 0.7422 0.3591 0.3031 0.063 Uiso 1 1 calc R . . H12C H 0.8216 0.5336 0.2831 0.063 Uiso 1 1 calc R . . C13 C 0.60755(8) 0.1544(2) 0.66869(7) 0.0215(3) Uani 1 1 d . . . O13 O 0.57524(6) 0.21922(16) 0.72430(5) 0.0257(2) Uani 1 1 d . . . O14 O 0.57400(6) -0.02020(16) 0.62501(5) 0.0245(2) Uani 1 1 d . . . C14 C 0.48463(8) -0.1279(2) 0.63607(7) 0.0239(3) Uani 1 1 d . . . C15 C 0.48510(9) -0.2373(2) 0.71144(8) 0.0287(3) Uani 1 1 d . . . H15A H 0.5347 -0.3525 0.7182 0.043 Uiso 1 1 calc R . . H15B H 0.4263 -0.3151 0.7160 0.043 Uiso 1 1 calc R . . H15C H 0.4946 -0.1149 0.7488 0.043 Uiso 1 1 calc R . . C16 C 0.40950(9) 0.0539(2) 0.62180(8) 0.0298(3) Uani 1 1 d . . . H16A H 0.4153 0.1725 0.6605 0.045 Uiso 1 1 calc R . . H16B H 0.3496 -0.0225 0.6212 0.045 Uiso 1 1 calc R . . H16C H 0.4151 0.1290 0.5745 0.045 Uiso 1 1 calc R . . C17 C 0.47776(10) -0.3160(2) 0.57755(8) 0.0314(3) Uani 1 1 d . . . H17A H 0.5269 -0.4307 0.5881 0.047 Uiso 1 1 calc R . . H17B H 0.4836 -0.2441 0.5298 0.047 Uiso 1 1 calc R . . H17C H 0.4183 -0.3948 0.5770 0.047 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 0.0261(5) 0.0281(6) 0.0201(5) -0.0031(4) 0.0045(4) -0.0053(4) C2 0.0278(6) 0.0274(7) 0.0210(6) -0.0028(5) 0.0022(5) -0.0055(5) C3 0.0279(6) 0.0282(7) 0.0255(6) 0.0000(5) 0.0014(5) -0.0031(5) C4 0.0248(6) 0.0272(7) 0.0227(6) 0.0010(5) 0.0029(5) -0.0038(5) C5 0.0263(6) 0.0268(7) 0.0199(6) -0.0014(5) 0.0045(5) -0.0026(5) O6 0.0314(5) 0.0283(5) 0.0260(5) 0.0007(4) -0.0014(4) -0.0086(4) C7 0.0308(7) 0.0345(8) 0.0258(7) -0.0031(6) 0.0042(5) -0.0054(6) C8 0.0307(7) 0.0357(8) 0.0275(7) -0.0032(6) 0.0068(5) -0.0097(6) O9 0.0311(5) 0.0412(6) 0.0289(5) -0.0047(4) 0.0099(4) -0.0134(4) O10 0.0354(5) 0.0413(6) 0.0229(5) -0.0063(4) 0.0103(4) -0.0168(4) C10 0.0274(6) 0.0367(8) 0.0240(6) -0.0011(5) 0.0073(5) -0.0086(6) C11 0.0423(8) 0.0411(9) 0.0417(9) -0.0054(7) 0.0167(7) -0.0049(7) C12 0.0351(8) 0.0581(11) 0.0331(8) 0.0077(7) 0.0028(6) -0.0062(7) C13 0.0216(6) 0.0218(6) 0.0208(6) 0.0025(5) 0.0002(4) 0.0013(5) O13 0.0275(5) 0.0290(5) 0.0211(4) -0.0011(4) 0.0052(4) -0.0012(4) O14 0.0235(4) 0.0259(5) 0.0248(4) -0.0031(4) 0.0061(3) -0.0044(3) C14 0.0203(6) 0.0230(6) 0.0287(7) 0.0016(5) 0.0036(5) -0.0025(5) C15 0.0282(6) 0.0270(7) 0.0316(7) 0.0056(5) 0.0071(5) 0.0006(5) C16 0.0261(6) 0.0273(7) 0.0357(7) 0.0032(6) 0.0009(5) 0.0009(5) C17 0.0327(7) 0.0265(7) 0.0347(7) -0.0031(6) 0.0018(6) -0.0048(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 N1 C2 1.4613(16) . ? N1 C5 1.4722(16) . ? N1 C13 1.3393(16) . ? C2 C3 1.5252(18) . ? C3 O6 1.4151(16) . ? C3 C4 1.5143(18) . ? C4 C7 1.4949(18) . ? C4 C5 1.5234(18) . ? C7 O10 1.4267(16) . ? C7 C8 1.5161(19) . ? C8 O9 1.4284(16) . ? O9 C10 1.4271(16) . ? O10 C10 1.4326(15) . ? C10 C11 1.502(2) . ? C10 C12 1.511(2) . ? C13 O13 1.2225(15) . ? C13 O14 1.3440(15) . ? O14 C14 1.4788(14) . ? C14 C15 1.5186(18) . ? C14 C16 1.5189(18) . ? C14 C17 1.5161(19) . ? 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 C13 N1 C2 121.27(10) . . ? C13 N1 C5 126.01(11) . . ? C2 N1 C5 112.20(10) . . ? N1 C2 C3 102.78(10) . . ? O6 C3 C4 111.52(11) . . ? O6 C3 C2 113.33(11) . . ? C4 C3 C2 103.53(10) . . ? C7 C4 C3 114.94(11) . . ? C7 C4 C5 114.17(11) . . ? C3 C4 C5 102.53(10) . . ? N1 C5 C4 102.40(10) . . ? O10 C7 C4 109.84(11) . . ? O10 C7 C8 101.86(11) . . ? C4 C7 C8 116.33(12) . . ? O9 C8 C7 101.90(11) . . ? C10 O9 C8 107.14(10) . . ? C7 O10 C10 108.14(10) . . ? O9 C10 O10 106.32(10) . . ? O9 C10 C11 108.32(11) . . ? O10 C10 C11 110.49(12) . . ? O9 C10 C12 110.37(12) . . ? O10 C10 C12 107.69(11) . . ? C11 C10 C12 113.42(13) . . ? O13 C13 N1 123.75(12) . . ? O13 C13 O14 125.08(11) . . ? N1 C13 O14 111.17(10) . . ? C13 O14 C14 120.45(9) . . ? O14 C14 C17 101.48(10) . . ? O14 C14 C15 111.49(10) . . ? C17 C14 C15 110.49(11) . . ? O14 C14 C16 109.29(10) . . ? C17 C14 C16 111.19(11) . . ? C15 C14 C16 112.38(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 C13 N1 C2 C3 178.55(11) . . . . ? C5 N1 C2 C3 -9.27(14) . . . . ? N1 C2 C3 O6 151.89(10) . . . . ? N1 C2 C3 C4 30.91(13) . . . . ? O6 C3 C4 C7 72.37(15) . . . . ? C2 C3 C4 C7 -165.44(12) . . . . ? O6 C3 C4 C5 -163.17(10) . . . . ? C2 C3 C4 C5 -40.98(13) . . . . ? C13 N1 C5 C4 155.90(12) . . . . ? C2 N1 C5 C4 -15.83(13) . . . . ? C7 C4 C5 N1 159.43(11) . . . . ? C3 C4 C5 N1 34.46(12) . . . . ? C3 C4 C7 O10 173.00(11) . . . . ? C5 C4 C7 O10 54.90(15) . . . . ? C3 C4 C7 C8 -72.01(16) . . . . ? C5 C4 C7 C8 169.89(11) . . . . ? O10 C7 C8 O9 -37.63(13) . . . . ? C4 C7 C8 O9 -157.03(11) . . . . ? C7 C8 O9 C10 33.54(14) . . . . ? C4 C7 O10 C10 152.46(12) . . . . ? C8 C7 O10 C10 28.57(14) . . . . ? C8 O9 C10 O10 -16.63(15) . . . . ? C8 O9 C10 C11 -135.40(12) . . . . ? C8 O9 C10 C12 99.89(13) . . . . ? C7 O10 C10 O9 -8.69(15) . . . . ? C7 O10 C10 C11 108.64(13) . . . . ? C7 O10 C10 C12 -126.99(13) . . . . ? C2 N1 C13 O13 -1.87(19) . . . . ? C5 N1 C13 O13 -172.91(12) . . . . ? C2 N1 C13 O14 178.18(10) . . . . ? C5 N1 C13 O14 7.14(17) . . . . ? O13 C13 O14 C14 9.01(18) . . . . ? N1 C13 O14 C14 -171.04(10) . . . . ? C13 O14 C14 C17 -178.04(10) . . . . ? C13 O14 C14 C15 -60.41(14) . . . . ? C13 O14 C14 C16 64.45(14) . . . . ? 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 O6 H6O O13 0.84 1.94 2.7506(13) 162 2_656 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.47 _refine_diff_density_min -0.23 _refine_diff_density_rms 0.04 #======END of CIF