# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Catrin Goeschen' 'Natalia Wibowo' 'Jonathan M. White' 'Uta Wille' _publ_contact_author_name 'Jonathan White' _publ_contact_author_email whitejm@unimelb.edu.au data_uta1 _database_code_depnum_ccdc_archive 'CCDC 810818' #TrackingRef 'uta1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 N4 O7' _chemical_formula_weight 350.29 _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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.3831(14) _cell_length_b 7.837(3) _cell_length_c 15.410(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.91(3) _cell_angle_gamma 90.00 _cell_volume 770.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 301 _cell_measurement_theta_min 5.7259 _cell_measurement_theta_max 72.8467 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1600 _exptl_crystal_size_mid 0.0800 _exptl_crystal_size_min 0.0200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 1.061 _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2249 _diffrn_reflns_av_R_equivalents 0.1101 _diffrn_reflns_av_sigmaI/netI 0.3643 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.74 _diffrn_reflns_theta_max 64.99 _reflns_number_total 1784 _reflns_number_gt 525 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 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 constr _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 0.6(7) _refine_ls_number_reflns 1784 _refine_ls_number_parameters 227 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2038 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0620 _refine_ls_goodness_of_fit_ref 0.615 _refine_ls_restrained_S_all 0.615 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 O3 O 0.5418(10) 0.1796(10) 0.3188(4) 0.040(2) Uani 1 1 d . . . O2 O 0.2660(11) 0.4336(9) 0.4249(5) 0.045(2) Uani 1 1 d . . . O1 O 0.1387(11) 0.1711(10) 0.4557(5) 0.047(2) Uani 1 1 d . . . O4 O 0.5721(11) -0.0150(9) 0.2194(5) 0.044(2) Uani 1 1 d . . . O7 O 0.1775(12) 0.7080(8) 0.2274(5) 0.048(2) Uani 1 1 d . . . O6 O 0.2461(10) -0.1782(8) -0.1465(4) 0.035(2) Uani 1 1 d . . . N2 N 0.2754(13) 0.4320(10) 0.1160(6) 0.034(3) Uani 1 1 d . . . H2 H 0.2675 0.5357 0.0979 0.041 Uiso 1 1 calc R . . N1 N 0.1230(15) 0.4352(10) 0.2606(6) 0.030(3) Uani 1 1 d . . . N3 N 0.4887(15) 0.1076(11) 0.2499(7) 0.044(3) Uani 1 1 d . . . N4 N 0.2454(13) -0.1791(11) -0.0659(7) 0.034(3) Uani 1 1 d . . . C9 C 0.0507(15) 0.2925(14) 0.3155(6) 0.033(3) Uani 1 1 d . . . H9 H -0.1013 0.3011 0.3225 0.040 Uiso 1 1 calc R . . C11 C 0.1587(16) 0.2900(16) 0.4059(6) 0.032(3) Uani 1 1 d . . . C1 C 0.2626(15) 0.2948(15) 0.0625(7) 0.026(3) Uani 1 1 d . . . C7 C 0.2916(16) 0.1817(13) 0.2060(7) 0.036(3) Uani 1 1 d . . . C3 C 0.2660(15) -0.0167(13) 0.0697(7) 0.032(3) Uani 1 1 d . . . H3 H 0.2718 -0.1189 0.1003 0.038 Uiso 1 1 calc R . . C4 C 0.2460(16) -0.0127(14) -0.0183(7) 0.027(3) Uani 1 1 d . . . C10 C 0.1010(16) 0.1320(11) 0.2624(7) 0.032(3) Uani 1 1 d . . . H10A H -0.0179 0.0998 0.2259 0.039 Uiso 1 1 calc R . . H10B H 0.1362 0.0372 0.3004 0.039 Uiso 1 1 calc R . . C6 C 0.2518(15) 0.2886(15) -0.0272(7) 0.032(3) Uani 1 1 d . . . H6 H 0.2498 0.3896 -0.0589 0.039 Uiso 1 1 calc R . . C13 C 0.3555(14) 0.4386(17) 0.5126(7) 0.071(5) Uani 1 1 d . . . H13A H 0.4288 0.5444 0.5211 0.106 Uiso 1 1 calc R . . H13B H 0.4513 0.3452 0.5203 0.106 Uiso 1 1 calc R . . H13C H 0.2453 0.4296 0.5540 0.106 Uiso 1 1 calc R . . C2 C 0.2772(16) 0.1410(13) 0.1116(7) 0.030(3) Uani 1 1 d . . . C14 C -0.1120(14) 0.6454(13) 0.3203(7) 0.048(3) Uani 1 1 d . . . H14A H -0.0753 0.6376 0.3808 0.072 Uiso 1 1 calc R . . H14B H -0.2215 0.5652 0.3069 0.072 Uiso 1 1 calc R . . H14C H -0.1599 0.7589 0.3073 0.072 Uiso 1 1 calc R . . C5 C 0.2442(15) 0.1373(13) -0.0692(7) 0.031(3) Uani 1 1 d . . . H5 H 0.2379 0.1321 -0.1294 0.038 Uiso 1 1 calc R . . C8 C 0.3035(18) 0.3864(11) 0.2064(8) 0.029(3) Uani 1 1 d . . . H8 H 0.4368 0.4283 0.2305 0.035 Uiso 1 1 calc R . . C12 C 0.073(2) 0.6064(14) 0.2678(9) 0.049(4) Uani 1 1 d . . . O5 O 0.2356(11) -0.3143(8) -0.0216(5) 0.037(2) Uani 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 O3 0.046(5) 0.033(5) 0.040(5) 0.009(5) 0.002(4) 0.001(4) O2 0.044(5) 0.044(5) 0.045(5) -0.003(4) -0.015(5) -0.018(4) O1 0.066(6) 0.036(5) 0.039(5) 0.002(5) 0.003(4) -0.008(4) O4 0.046(5) 0.024(4) 0.062(6) 0.003(5) 0.000(4) -0.004(4) O7 0.076(6) 0.013(4) 0.055(6) 0.001(4) 0.009(5) 0.005(4) O6 0.050(5) 0.022(4) 0.032(5) -0.007(4) 0.002(4) 0.000(4) N2 0.038(7) 0.023(5) 0.041(7) 0.002(5) 0.003(6) -0.001(5) N1 0.031(6) 0.031(5) 0.029(6) -0.004(5) -0.011(5) 0.000(5) N3 0.050(8) 0.032(6) 0.051(8) 0.008(6) 0.012(6) -0.005(5) N4 0.009(6) 0.032(6) 0.061(8) -0.017(6) 0.004(5) -0.013(4) C9 0.040(8) 0.029(6) 0.031(7) 0.002(7) -0.001(6) 0.001(7) C11 0.036(8) 0.040(7) 0.021(6) -0.016(7) 0.005(6) -0.004(7) C1 0.019(7) 0.024(5) 0.036(7) 0.007(6) -0.010(5) 0.003(6) C7 0.023(7) 0.019(5) 0.064(9) 0.004(7) -0.030(7) 0.002(5) C3 0.042(8) 0.017(5) 0.037(7) -0.004(6) -0.009(6) 0.004(6) C4 0.027(7) 0.019(5) 0.036(8) -0.011(6) -0.003(6) 0.007(5) C10 0.042(8) 0.017(6) 0.038(8) -0.003(6) 0.015(7) -0.013(6) C6 0.040(8) 0.026(6) 0.030(8) -0.004(7) -0.006(6) 0.000(6) C13 0.087(11) 0.064(9) 0.061(11) -0.002(9) -0.032(9) -0.030(9) C2 0.025(8) 0.030(7) 0.036(8) -0.011(6) 0.002(6) 0.005(6) C14 0.059(8) 0.022(5) 0.063(8) -0.008(6) 0.003(7) 0.004(6) C5 0.032(7) 0.045(7) 0.017(6) 0.004(6) -0.010(5) 0.003(6) C8 0.028(8) 0.010(5) 0.049(8) -0.010(5) -0.001(7) -0.007(5) C12 0.051(10) 0.034(7) 0.060(10) -0.013(7) -0.019(8) 0.022(7) O5 0.062(6) 0.015(4) 0.036(5) 0.001(4) 0.012(4) -0.001(4) _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 O3 N3 1.244(10) . ? O2 C11 1.347(12) . ? O2 C13 1.460(10) . ? O1 C11 1.215(12) . ? O4 N3 1.198(10) . ? O7 C12 1.215(14) . ? O6 N4 1.243(10) . ? N2 C1 1.356(13) . ? N2 C8 1.447(12) . ? N1 C12 1.383(12) . ? N1 C8 1.484(12) . ? N1 C9 1.481(12) . ? N3 C7 1.533(12) . ? N4 O5 1.262(10) . ? N4 C4 1.496(12) . ? C9 C10 1.538(12) . ? C9 C11 1.545(12) . ? C1 C6 1.383(14) . ? C1 C2 1.426(14) . ? C7 C2 1.491(14) . ? C7 C10 1.556(13) . ? C7 C8 1.606(11) . ? C3 C4 1.361(13) . ? C3 C2 1.395(13) . ? C4 C5 1.413(13) . ? C6 C5 1.352(13) . ? C14 C12 1.476(14) . ? 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 C11 O2 C13 114.4(9) . . ? C1 N2 C8 113.3(8) . . ? C12 N1 C8 118.4(10) . . ? C12 N1 C9 127.8(11) . . ? C8 N1 C9 112.3(8) . . ? O4 N3 O3 125.6(10) . . ? O4 N3 C7 119.8(10) . . ? O3 N3 C7 114.6(9) . . ? O6 N4 O5 123.1(9) . . ? O6 N4 C4 119.0(10) . . ? O5 N4 C4 117.8(9) . . ? N1 C9 C10 104.1(8) . . ? N1 C9 C11 112.8(9) . . ? C10 C9 C11 112.1(9) . . ? O1 C11 O2 124.1(9) . . ? O1 C11 C9 122.0(11) . . ? O2 C11 C9 113.8(10) . . ? N2 C1 C6 129.5(11) . . ? N2 C1 C2 110.2(8) . . ? C6 C1 C2 120.1(12) . . ? C2 C7 N3 112.8(9) . . ? C2 C7 C10 117.1(9) . . ? N3 C7 C10 107.6(9) . . ? C2 C7 C8 102.7(9) . . ? N3 C7 C8 109.7(9) . . ? C10 C7 C8 106.6(10) . . ? C4 C3 C2 116.3(11) . . ? C3 C4 C5 124.9(10) . . ? C3 C4 N4 117.9(10) . . ? C5 C4 N4 116.9(9) . . ? C9 C10 C7 105.3(8) . . ? C5 C6 C1 120.7(12) . . ? C3 C2 C1 120.1(10) . . ? C3 C2 C7 130.0(10) . . ? C1 C2 C7 109.8(9) . . ? C6 C5 C4 117.7(10) . . ? N2 C8 N1 113.1(9) . . ? N2 C8 C7 103.8(9) . . ? N1 C8 C7 102.8(9) . . ? O7 C12 N1 117.8(12) . . ? O7 C12 C14 126.5(11) . . ? N1 C12 C14 115.6(13) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.212 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.055