# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name D.B.Ramachary M.S.Prasad R.Madhavachary _publ_contact_author_name 'Dhevalapally B. Ramachary' _publ_contact_author_email ramsc@uohyd.ernet.in data_dbr15a _database_code_depnum_ccdc_archive 'CCDC 795663' #TrackingRef 'DBR15A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N O5' _chemical_formula_weight 249.22 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_cell_setting ? _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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.6366(2) _cell_length_b 12.6433(7) _cell_length_c 16.9777(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1209.92(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2251 _cell_measurement_theta_min 2.6004 _cell_measurement_theta_max 61.1386 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.53804 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3291 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2839 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 61.22 _reflns_number_total 1782 _reflns_number_gt 1669 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1997P)^2^+0.0807P] 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 -0.1(5) _refine_ls_number_reflns 1782 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0920 _refine_ls_wR_factor_ref 0.2354 _refine_ls_wR_factor_gt 0.2279 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.004 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 1.1298(4) 0.5429(2) 0.27624(13) 0.0467(7) Uani 1 1 d . . . N1 N 1.0487(6) 0.8031(3) 0.2644(2) 0.0589(10) Uani 1 1 d . . . O5 O 1.3754(5) 0.4529(2) 0.38734(15) 0.0587(8) Uani 1 1 d . . . C C 1.1955(6) 0.5160(3) 0.4120(2) 0.0452(9) Uani 1 1 d . . . C0AA C 0.8676(7) 0.6286(3) 0.37069(19) 0.0434(9) Uani 1 1 d . . . O2 O 1.0542(6) 0.5415(3) 0.15037(15) 0.0634(9) Uani 1 1 d . . . C1AA C 0.9814(7) 0.5610(3) 0.21438(19) 0.0420(8) Uani 1 1 d . . . C2AA C 0.7272(6) 0.6755(3) 0.3041(2) 0.0440(9) Uani 1 1 d . . . H2A H 0.5617 0.6758 0.3218 0.053 Uiso 1 1 calc R . . C3AA C 1.0603(6) 0.5629(3) 0.35364(19) 0.0417(8) Uani 1 1 d . . . C4AA C 1.1404(8) 0.5365(3) 0.4908(2) 0.0569(10) Uani 1 1 d . . . H4A H 1.2299 0.5066 0.5311 0.068 Uiso 1 1 calc R . . O3 O 1.0937(8) 0.7958(4) 0.1952(3) 0.1032(14) Uani 1 1 d . . . O4 O 1.1941(7) 0.8146(4) 0.3149(3) 0.1006(14) Uani 1 1 d . . . C5AA C 0.9502(9) 0.6020(4) 0.5080(2) 0.0609(11) Uani 1 1 d . . . H5A H 0.9127 0.6155 0.5603 0.073 Uiso 1 1 calc R . . C6AA C 0.7351(6) 0.6011(3) 0.2323(2) 0.0459(9) Uani 1 1 d . . . H6A H 0.6430 0.5386 0.2475 0.055 Uiso 1 1 calc R . . C7AA C 0.8166(8) 0.6471(3) 0.4501(2) 0.0551(10) Uani 1 1 d . . . H7A H 0.6900 0.6906 0.4636 0.066 Uiso 1 1 calc R . . C8AA C 1.5079(9) 0.3971(4) 0.4453(3) 0.0677(12) Uani 1 1 d . . . H8AA H 1.6268 0.3547 0.4200 0.102 Uiso 1 1 calc R . . H8AC H 1.4034 0.3522 0.4750 0.102 Uiso 1 1 calc R . . H8AB H 1.5829 0.4467 0.4801 0.102 Uiso 1 1 calc R . . C9AA C 0.7911(7) 0.7922(3) 0.2879(2) 0.0501(10) Uani 1 1 d . . . H9AA H 0.6910 0.8193 0.2461 0.060 Uiso 1 1 calc R . . H9AB H 0.7614 0.8339 0.3349 0.060 Uiso 1 1 calc R . . C0BA C 0.6176(8) 0.6432(4) 0.1584(3) 0.0683(13) Uani 1 1 d . . . H0BB H 0.7187 0.6950 0.1343 0.102 Uiso 1 1 calc R . . H0BA H 0.4686 0.6752 0.1719 0.102 Uiso 1 1 calc R . . H0BC H 0.5911 0.5861 0.1222 0.102 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 0.0353(13) 0.0677(15) 0.0371(13) 0.0023(10) 0.0044(10) 0.0084(12) N1 0.043(2) 0.0453(16) 0.089(3) 0.0037(16) 0.014(2) -0.0020(15) O5 0.0464(16) 0.0819(18) 0.0478(14) -0.0007(12) -0.0064(12) 0.0155(15) C 0.0370(19) 0.0537(18) 0.0448(18) -0.0054(14) -0.0010(16) -0.0018(16) C0AA 0.0371(19) 0.0508(19) 0.0425(18) -0.0009(12) 0.0109(14) -0.0040(16) O2 0.0638(19) 0.0854(19) 0.0409(14) -0.0043(12) 0.0041(13) 0.0170(16) C1AA 0.0386(19) 0.0493(18) 0.0382(16) -0.0008(13) 0.0044(15) 0.0015(15) C2AA 0.0268(16) 0.0519(19) 0.0533(19) -0.0008(15) 0.0086(16) 0.0024(14) C3AA 0.0338(17) 0.0540(18) 0.0371(17) -0.0002(13) 0.0048(15) -0.0031(16) C4AA 0.054(2) 0.076(2) 0.0407(18) 0.0019(17) -0.0035(17) -0.008(2) O3 0.076(3) 0.129(3) 0.105(3) 0.008(2) 0.039(3) -0.010(3) O4 0.0488(19) 0.119(3) 0.134(3) -0.019(3) -0.019(3) -0.012(2) C5AA 0.066(3) 0.076(2) 0.0406(18) -0.0094(17) 0.009(2) -0.008(2) C6AA 0.0337(18) 0.0518(19) 0.0521(19) 0.0009(15) 0.0001(16) -0.0061(15) C7AA 0.053(2) 0.0596(19) 0.053(2) -0.0093(16) 0.016(2) -0.003(2) C8AA 0.064(3) 0.075(2) 0.064(2) 0.000(2) -0.020(2) 0.016(2) C9AA 0.0351(19) 0.0507(19) 0.064(2) 0.0002(16) 0.0101(17) 0.0046(16) C0BA 0.050(2) 0.089(3) 0.067(3) -0.006(2) -0.019(2) -0.001(2) _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 C1AA 1.362(4) . ? O1 C3AA 1.394(4) . ? N1 O4 1.195(6) . ? N1 O3 1.206(6) . ? N1 C9AA 1.512(5) . ? O5 C 1.356(5) . ? O5 C8AA 1.423(5) . ? C C3AA 1.384(5) . ? C C4AA 1.397(5) . ? C0AA C3AA 1.398(5) . ? C0AA C7AA 1.399(5) . ? C0AA C2AA 1.501(5) . ? O2 C1AA 1.187(4) . ? C1AA C6AA 1.509(5) . ? C2AA C6AA 1.541(5) . ? C2AA C9AA 1.544(5) . ? C4AA C5AA 1.386(7) . ? C5AA C7AA 1.362(7) . ? C6AA C0BA 1.515(6) . ? 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 C1AA O1 C3AA 121.6(3) . . ? O4 N1 O3 124.3(5) . . ? O4 N1 C9AA 118.7(4) . . ? O3 N1 C9AA 116.9(4) . . ? C O5 C8AA 118.1(3) . . ? O5 C C3AA 116.3(3) . . ? O5 C C4AA 124.8(3) . . ? C3AA C C4AA 118.9(4) . . ? C3AA C0AA C7AA 117.3(4) . . ? C3AA C0AA C2AA 119.2(3) . . ? C7AA C0AA C2AA 123.5(3) . . ? O2 C1AA O1 117.3(3) . . ? O2 C1AA C6AA 124.9(3) . . ? O1 C1AA C6AA 117.8(3) . . ? C0AA C2AA C6AA 109.9(3) . . ? C0AA C2AA C9AA 112.8(3) . . ? C6AA C2AA C9AA 115.9(3) . . ? C C3AA O1 116.2(3) . . ? C C3AA C0AA 122.3(3) . . ? O1 C3AA C0AA 121.4(3) . . ? C5AA C4AA C 119.0(4) . . ? C7AA C5AA C4AA 121.7(4) . . ? C1AA C6AA C0BA 110.7(3) . . ? C1AA C6AA C2AA 113.0(3) . . ? C0BA C6AA C2AA 115.3(3) . . ? C5AA C7AA C0AA 120.8(4) . . ? N1 C9AA C2AA 111.0(3) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 61.14 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.394 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.121