# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email cruz@ccdc.cam.ac.uk _publ_contact_author_name 'Aurora J. Cruz-Cabeza' loop_ _publ_author_name 'Alaina M. Moragues-Bartolome' 'William Jones' 'Aurora J.Cruz-Cabeza' data_1h _database_code_depnum_ccdc_archive 'CCDC 832268' #TrackingRef '6068_web_deposit_cif_file_0_AuroraJ.Cruz-Cabeza_1309426426.1h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 N O4, C4 H7 N O' _chemical_formula_sum 'C11 H12 N2 O5' _chemical_formula_weight 252.23 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 P2(1)/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 5.8384(2) _cell_length_b 9.1212(3) _cell_length_c 22.1209(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.571(2) _cell_angle_gamma 90.00 _cell_volume 1174.26(7) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5377 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8336 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2683 _reflns_number_gt 1816 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0678P)^2^+0.4329P] 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_number_reflns 2683 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _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 C1 C 0.0710(3) 0.7142(2) 0.30450(9) 0.0412(5) Uani 1 1 d . . . C2 C -0.0309(4) 0.8248(3) 0.25978(11) 0.0598(7) Uani 1 1 d . . . H2A H -0.1913 0.7987 0.2461 0.072 Uiso 1 1 calc R . . H2B H -0.0291 0.9240 0.2780 0.072 Uiso 1 1 calc R . . C3 C 0.1170(6) 0.8191(3) 0.20881(12) 0.0843(10) Uani 1 1 d . . . H3A H 0.1793 0.9178 0.2012 0.101 Uiso 1 1 calc R . . H3B H 0.0270 0.7857 0.1715 0.101 Uiso 1 1 calc R . . C4 C 0.3074(4) 0.7153(3) 0.22505(11) 0.0660(7) Uani 1 1 d . . . H4A H 0.3100 0.6356 0.1947 0.079 Uiso 1 1 calc R . . H4B H 0.4574 0.7665 0.2277 0.079 Uiso 1 1 calc R . . N5 N 0.2576(3) 0.65806(19) 0.28372(8) 0.0447(4) Uani 1 1 d . . . H5 H 0.3437 0.5920 0.3036 0.054 Uiso 1 1 calc R . . O6 O -0.0063(3) 0.68249(17) 0.35382(7) 0.0532(4) Uani 1 1 d . . . C7 C 0.4372(3) 0.3202(2) 0.46604(8) 0.0354(4) Uani 1 1 d . . . C8 C 0.6407(3) 0.2469(2) 0.45831(9) 0.0397(5) Uani 1 1 d . . . H8 H 0.7157 0.2610 0.4222 0.048 Uiso 1 1 calc R . . C9 C 0.7352(4) 0.1536(2) 0.50267(9) 0.0407(5) Uani 1 1 d . . . H9 H 0.8751 0.1035 0.4977 0.049 Uiso 1 1 calc R . . C10 C 0.6208(3) 0.1352(2) 0.55453(8) 0.0373(4) Uani 1 1 d . . . C11 C 0.4190(3) 0.2072(2) 0.56384(9) 0.0407(5) Uani 1 1 d . . . H11 H 0.3448 0.1927 0.6001 0.049 Uiso 1 1 calc R . . C12 C 0.3271(3) 0.3011(2) 0.51911(9) 0.0401(5) Uani 1 1 d . . . H12 H 0.1889 0.3525 0.5246 0.048 Uiso 1 1 calc R . . C13 C 0.3420(3) 0.4203(2) 0.41671(8) 0.0376(4) Uani 1 1 d . . . O14 O 0.1553(2) 0.49074(17) 0.42990(6) 0.0462(4) Uani 1 1 d . . . H14 H 0.104(4) 0.556(3) 0.3978(11) 0.055 Uiso 1 1 d . . . O15 O 0.4308(2) 0.43413(17) 0.36923(6) 0.0494(4) Uani 1 1 d . . . N16 N 0.7196(3) 0.03391(19) 0.60170(7) 0.0443(4) Uani 1 1 d . . . O17 O 0.8976(3) -0.03069(19) 0.59258(7) 0.0613(5) Uani 1 1 d . . . O18 O 0.6191(3) 0.01871(18) 0.64763(7) 0.0563(4) 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 C1 0.0402(11) 0.0393(10) 0.0440(11) -0.0031(9) 0.0018(8) -0.0005(9) C2 0.0464(13) 0.0714(17) 0.0612(15) 0.0174(12) 0.0011(11) 0.0108(12) C3 0.117(3) 0.083(2) 0.0552(15) 0.0206(14) 0.0247(16) 0.0449(19) C4 0.0580(15) 0.0785(18) 0.0640(15) 0.0253(14) 0.0201(12) 0.0099(14) N5 0.0464(10) 0.0435(10) 0.0448(9) 0.0037(8) 0.0076(8) 0.0079(8) O6 0.0533(9) 0.0582(10) 0.0495(9) 0.0051(7) 0.0135(7) 0.0158(8) C7 0.0368(10) 0.0351(10) 0.0347(10) -0.0070(8) 0.0045(8) -0.0040(8) C8 0.0427(11) 0.0411(11) 0.0368(10) -0.0031(8) 0.0130(8) 0.0000(9) C9 0.0408(11) 0.0400(11) 0.0422(11) -0.0032(9) 0.0087(8) 0.0030(9) C10 0.0426(11) 0.0332(10) 0.0359(10) -0.0024(8) 0.0028(8) -0.0044(8) C11 0.0442(11) 0.0437(11) 0.0354(10) -0.0021(9) 0.0108(8) -0.0047(9) C12 0.0362(10) 0.0441(12) 0.0408(10) -0.0069(9) 0.0092(8) -0.0007(9) C13 0.0376(10) 0.0386(11) 0.0368(10) -0.0062(8) 0.0040(8) -0.0018(9) O14 0.0439(8) 0.0553(9) 0.0401(8) 0.0024(7) 0.0079(6) 0.0119(7) O15 0.0548(9) 0.0560(10) 0.0389(8) 0.0049(7) 0.0130(6) 0.0146(7) N16 0.0564(11) 0.0373(9) 0.0393(9) -0.0002(7) 0.0049(8) -0.0035(8) O17 0.0704(11) 0.0589(10) 0.0550(10) 0.0077(8) 0.0079(8) 0.0216(9) O18 0.0678(11) 0.0583(10) 0.0441(8) 0.0099(7) 0.0124(7) -0.0050(8) _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 C1 O6 1.248(2) . ? C1 N5 1.319(3) . ? C1 C2 1.502(3) . ? C2 C3 1.475(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.482(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N5 1.450(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N5 H5 0.8800 . ? C7 C8 1.385(3) . ? C7 C12 1.394(3) . ? C7 C13 1.496(3) . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 C11 1.379(3) . ? C10 N16 1.476(3) . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 O15 1.214(2) . ? C13 O14 1.317(2) . ? O14 H14 0.96(3) . ? N16 O18 1.221(2) . ? N16 O17 1.225(2) . ? 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 O6 C1 N5 125.52(19) . . ? O6 C1 C2 125.42(19) . . ? N5 C1 C2 109.04(18) . . ? C3 C2 C1 104.7(2) . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2B 110.8 . . ? C1 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? C2 C3 C4 108.1(2) . . ? C2 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? C2 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N5 C4 C3 104.31(19) . . ? N5 C4 H4A 110.9 . . ? C3 C4 H4A 110.9 . . ? N5 C4 H4B 110.9 . . ? C3 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? C1 N5 C4 113.71(19) . . ? C1 N5 H5 123.1 . . ? C4 N5 H5 123.1 . . ? C8 C7 C12 120.08(18) . . ? C8 C7 C13 118.49(16) . . ? C12 C7 C13 121.43(17) . . ? C9 C8 C7 120.52(18) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 118.20(18) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C11 C10 C9 122.74(19) . . ? C11 C10 N16 118.89(17) . . ? C9 C10 N16 118.37(18) . . ? C10 C11 C12 118.36(18) . . ? C10 C11 H11 120.8 . . ? C12 C11 H11 120.8 . . ? C11 C12 C7 120.10(18) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? O15 C13 O14 123.98(19) . . ? O15 C13 C7 122.32(17) . . ? O14 C13 C7 113.71(16) . . ? C13 O14 H14 110.8(14) . . ? O18 N16 O17 123.54(18) . . ? O18 N16 C10 118.21(18) . . ? O17 N16 C10 118.25(17) . . ? 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 O6 C1 C2 C3 -178.4(2) . . . . ? N5 C1 C2 C3 2.7(3) . . . . ? C1 C2 C3 C4 -3.4(3) . . . . ? C2 C3 C4 N5 2.9(3) . . . . ? O6 C1 N5 C4 -179.9(2) . . . . ? C2 C1 N5 C4 -1.0(3) . . . . ? C3 C4 N5 C1 -1.2(3) . . . . ? C12 C7 C8 C9 0.5(3) . . . . ? C13 C7 C8 C9 179.88(18) . . . . ? C7 C8 C9 C10 0.3(3) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C8 C9 C10 N16 179.16(17) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? N16 C10 C11 C12 -179.56(17) . . . . ? C10 C11 C12 C7 0.5(3) . . . . ? C8 C7 C12 C11 -0.9(3) . . . . ? C13 C7 C12 C11 179.72(18) . . . . ? C8 C7 C13 O15 3.5(3) . . . . ? C12 C7 C13 O15 -177.16(19) . . . . ? C8 C7 C13 O14 -176.45(17) . . . . ? C12 C7 C13 O14 2.9(3) . . . . ? C11 C10 N16 O18 -0.6(3) . . . . ? C9 C10 N16 O18 179.43(18) . . . . ? C11 C10 N16 O17 179.18(18) . . . . ? C9 C10 N16 O17 -0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.312 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.046 # Attachment '6069_web_deposit_cif_file_1_AuroraJ.Cruz-Cabeza_1309426426.1k.cif' data_1k _database_code_depnum_ccdc_archive 'CCDC 832269' #TrackingRef '6069_web_deposit_cif_file_1_AuroraJ.Cruz-Cabeza_1309426426.1k.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O6, C4 H7 N O' _chemical_formula_sum 'C11 H11 N3 O7' _chemical_formula_weight 297.23 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 P2(1)/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 11.4528(5) _cell_length_b 6.3801(3) _cell_length_c 17.643(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.489(2) _cell_angle_gamma 90.00 _cell_volume 1289.13(11) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 13810 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 20.82 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poorly diffracting crystal (theta(max) = 20 deg). The -NH and -COOH hydrogen were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7418 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 20.77 _reflns_number_total 1330 _reflns_number_gt 1094 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0535P)^2^+0.3401P] 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_number_reflns 1330 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.000 _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 0.56371(16) -0.5994(3) 0.10387(13) 0.0393(6) Uani 1 1 d . . . H1 H 0.5592(19) -0.681(4) 0.0516(14) 0.047 Uiso 1 1 d . . . C2 C 0.6076(2) -0.6875(4) 0.17476(15) 0.0495(8) Uani 1 1 d . . . H2A H 0.6834 -0.7591 0.1673 0.059 Uiso 1 1 calc R . . H2B H 0.5513 -0.7882 0.1964 0.059 Uiso 1 1 calc R . . C3 C 0.6217(2) -0.4951(4) 0.22570(16) 0.0514(7) Uani 1 1 d . . . H3A H 0.7022 -0.4389 0.2234 0.062 Uiso 1 1 calc R . . H3B H 0.6030 -0.5290 0.2790 0.062 Uiso 1 1 calc R . . C4 C 0.5337(2) -0.3398(4) 0.19219(15) 0.0498(7) Uani 1 1 d . . . H4A H 0.4587 -0.3457 0.2196 0.060 Uiso 1 1 calc R . . H4B H 0.5643 -0.1948 0.1943 0.060 Uiso 1 1 calc R . . C5 C 0.5190(2) -0.4111(4) 0.11270(15) 0.0366(6) Uani 1 1 d . . . O6 O 0.47020(16) -0.3112(3) 0.05995(11) 0.0549(6) Uani 1 1 d . . . C7 C 0.1969(2) 0.3874(4) -0.03133(15) 0.0393(7) Uani 1 1 d . . . H7 H 0.2020 0.3228 -0.0797 0.047 Uiso 1 1 calc R . . C8 C 0.24734(19) 0.2939(3) 0.03166(15) 0.0349(6) Uani 1 1 d . . . C9 C 0.2369(2) 0.3864(3) 0.10214(14) 0.0380(7) Uani 1 1 d . . . H9 H 0.2704 0.3229 0.1459 0.046 Uiso 1 1 calc R . . C10 C 0.1761(2) 0.5745(4) 0.10755(15) 0.0392(7) Uani 1 1 d . . . C11 C 0.1276(2) 0.6728(4) 0.04583(16) 0.0422(7) Uani 1 1 d . . . H11 H 0.0877 0.8026 0.0505 0.051 Uiso 1 1 calc R . . C12 C 0.1391(2) 0.5755(4) -0.02303(15) 0.0391(7) Uani 1 1 d . . . C13 C 0.3114(2) 0.0910(4) 0.02156(17) 0.0392(7) Uani 1 1 d . . . O14 O 0.36661(16) 0.0316(3) 0.08265(11) 0.0514(6) Uani 1 1 d . . . H14 H 0.402(2) -0.082(4) 0.0770(15) 0.062 Uiso 1 1 d . . . O15 O 0.30983(15) -0.0026(3) -0.03840(11) 0.0521(5) Uani 1 1 d . . . N16 N 0.1614(2) 0.6716(4) 0.18251(15) 0.0554(7) Uani 1 1 d . . . O17 O 0.2062(2) 0.5887(3) 0.23685(13) 0.0862(8) Uani 1 1 d . . . O18 O 0.10359(19) 0.8301(3) 0.18656(12) 0.0808(7) Uani 1 1 d . . . N19 N 0.08491(19) 0.6746(4) -0.09051(16) 0.0548(7) Uani 1 1 d . . . O20 O 0.03448(18) 0.8412(3) -0.08199(12) 0.0740(7) Uani 1 1 d . . . O21 O 0.09190(18) 0.5823(4) -0.15107(13) 0.0724(7) 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 N1 0.0462(13) 0.0314(13) 0.0404(15) -0.0016(10) -0.0038(11) 0.0036(10) C2 0.0548(17) 0.0407(15) 0.053(2) 0.0007(14) -0.0001(14) 0.0057(12) C3 0.0579(17) 0.0540(17) 0.0424(19) -0.0029(14) -0.0038(13) -0.0005(14) C4 0.0673(19) 0.0373(14) 0.045(2) -0.0053(13) 0.0032(14) 0.0012(13) C5 0.0401(15) 0.0294(15) 0.0401(19) 0.0021(13) -0.0016(12) 0.0008(12) O6 0.0679(13) 0.0408(10) 0.0561(14) -0.0059(9) -0.0039(10) 0.0087(9) C7 0.0398(15) 0.0416(15) 0.0367(17) 0.0015(13) 0.0042(13) -0.0040(12) C8 0.0357(14) 0.0313(13) 0.0378(17) 0.0004(13) 0.0010(12) -0.0040(11) C9 0.0423(15) 0.0352(14) 0.0366(18) 0.0033(13) -0.0017(12) -0.0003(11) C10 0.0406(15) 0.0361(15) 0.0411(19) -0.0054(13) 0.0001(13) 0.0001(12) C11 0.0362(15) 0.0353(14) 0.055(2) 0.0045(14) 0.0014(13) 0.0014(11) C12 0.0351(14) 0.0430(15) 0.0391(18) 0.0109(14) 0.0008(12) -0.0009(12) C13 0.0429(16) 0.0335(14) 0.0411(19) 0.0023(15) 0.0013(14) -0.0042(12) O14 0.0704(13) 0.0364(10) 0.0473(14) -0.0047(9) -0.0057(10) 0.0178(9) O15 0.0661(13) 0.0443(11) 0.0457(14) -0.0109(10) -0.0017(9) 0.0059(9) N16 0.0607(16) 0.0534(16) 0.0521(19) -0.0132(14) -0.0031(13) 0.0083(13) O17 0.132(2) 0.0800(15) 0.0467(15) -0.0181(12) -0.0137(14) 0.0395(14) O18 0.0890(16) 0.0697(14) 0.0836(18) -0.0303(12) -0.0065(12) 0.0377(13) N19 0.0453(15) 0.0639(17) 0.055(2) 0.0211(14) 0.0041(13) 0.0025(13) O20 0.0729(15) 0.0691(14) 0.0801(17) 0.0249(12) 0.0015(11) 0.0273(12) O21 0.0785(15) 0.0925(16) 0.0462(15) 0.0169(13) -0.0004(11) 0.0141(12) _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 C5 1.316(3) . ? N1 C2 1.457(3) . ? N1 H1 1.06(2) . ? C2 C3 1.529(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.529(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.482(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O6 1.255(3) . ? C7 C12 1.379(3) . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C9 1.383(3) . ? C8 C13 1.499(3) . ? C9 C10 1.391(3) . ? C9 H9 0.9500 . ? C10 C11 1.370(3) . ? C10 N16 1.471(3) . ? C11 C12 1.371(3) . ? C11 H11 0.9500 . ? C12 N19 1.480(3) . ? C13 O15 1.215(3) . ? C13 O14 1.301(3) . ? O14 H14 0.84(3) . ? N16 O17 1.206(3) . ? N16 O18 1.211(3) . ? N19 O20 1.220(3) . ? N19 O21 1.223(3) . ? 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 C5 N1 C2 112.5(2) . . ? C5 N1 H1 122.4(13) . . ? C2 N1 H1 124.8(13) . . ? N1 C2 C3 103.2(2) . . ? N1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? N1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? C2 C3 C4 103.1(2) . . ? C2 C3 H3A 111.1 . . ? C4 C3 H3A 111.1 . . ? C2 C3 H3B 111.1 . . ? C4 C3 H3B 111.1 . . ? H3A C3 H3B 109.1 . . ? C5 C4 C3 103.7(2) . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? O6 C5 N1 123.2(2) . . ? O6 C5 C4 126.3(2) . . ? N1 C5 C4 110.5(2) . . ? C12 C7 C8 119.2(2) . . ? C12 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 120.0(2) . . ? C9 C8 C13 121.5(2) . . ? C7 C8 C13 118.6(2) . . ? C8 C9 C10 118.5(2) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C11 C10 C9 122.7(2) . . ? C11 C10 N16 118.2(2) . . ? C9 C10 N16 119.1(2) . . ? C10 C11 C12 117.1(2) . . ? C10 C11 H11 121.4 . . ? C12 C11 H11 121.4 . . ? C11 C12 C7 122.5(2) . . ? C11 C12 N19 118.5(2) . . ? C7 C12 N19 119.0(3) . . ? O15 C13 O14 125.5(2) . . ? O15 C13 C8 121.6(3) . . ? O14 C13 C8 112.8(2) . . ? C13 O14 H14 112.6(19) . . ? O17 N16 O18 123.3(2) . . ? O17 N16 C10 118.6(2) . . ? O18 N16 C10 118.1(3) . . ? O20 N19 O21 124.2(2) . . ? O20 N19 C12 118.0(3) . . ? O21 N19 C12 117.8(2) . . ? 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 C3 -18.9(3) . . . . ? N1 C2 C3 C4 25.5(3) . . . . ? C2 C3 C4 C5 -23.7(3) . . . . ? C2 N1 C5 O6 -175.8(2) . . . . ? C2 N1 C5 C4 3.5(3) . . . . ? C3 C4 C5 O6 -167.2(2) . . . . ? C3 C4 C5 N1 13.5(3) . . . . ? C12 C7 C8 C9 1.6(3) . . . . ? C12 C7 C8 C13 -179.13(19) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C13 C8 C9 C10 -179.9(2) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C8 C9 C10 N16 178.2(2) . . . . ? C9 C10 C11 C12 1.3(3) . . . . ? N16 C10 C11 C12 -177.78(19) . . . . ? C10 C11 C12 C7 -0.3(3) . . . . ? C10 C11 C12 N19 178.4(2) . . . . ? C8 C7 C12 C11 -1.2(3) . . . . ? C8 C7 C12 N19 -179.8(2) . . . . ? C9 C8 C13 O15 171.7(2) . . . . ? C7 C8 C13 O15 -7.6(3) . . . . ? C9 C8 C13 O14 -8.5(3) . . . . ? C7 C8 C13 O14 172.2(2) . . . . ? C11 C10 N16 O17 -178.2(2) . . . . ? C9 C10 N16 O17 2.7(4) . . . . ? C11 C10 N16 O18 2.5(3) . . . . ? C9 C10 N16 O18 -176.6(2) . . . . ? C11 C12 N19 O20 1.5(3) . . . . ? C7 C12 N19 O20 -179.8(2) . . . . ? C11 C12 N19 O21 -177.2(2) . . . . ? C7 C12 N19 O21 1.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 20.77 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.297 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.044 # Attachment '6070_web_deposit_cif_file_2_AuroraJ.Cruz-Cabeza_1309426426.2f.cif' data_2f _database_code_depnum_ccdc_archive 'CCDC 832270' #TrackingRef '6070_web_deposit_cif_file_2_AuroraJ.Cruz-Cabeza_1309426426.2f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H5 F3 O2, C5 H9 N O' _chemical_formula_sum 'C13 H14 F3 N O3' _chemical_formula_weight 289.25 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' 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 10.8821(4) _cell_length_b 7.6597(3) _cell_length_c 16.4743(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.612(3) _cell_angle_gamma 90.00 _cell_volume 1334.62(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5773 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -CF3 group is disordered over two sites. The -NH and -COOH hydrogen atoms were located and their positions were refined satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7348 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.36 _reflns_number_total 2406 _reflns_number_gt 1793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0736P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2406 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _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 C1 C 0.77460(14) -0.4747(2) 0.04762(9) 0.0455(4) Uani 1 1 d . A . C2 C 0.74213(15) -0.4173(2) 0.11978(10) 0.0503(4) Uani 1 1 d . . . H2 H 0.6864 -0.4845 0.1438 0.060 Uiso 1 1 calc R . . C3 C 0.79113(15) -0.2626(2) 0.15640(9) 0.0481(4) Uani 1 1 d . . . H3 H 0.7693 -0.2237 0.2059 0.058 Uiso 1 1 calc R . . C4 C 0.87195(13) -0.1633(2) 0.12151(8) 0.0426(4) Uani 1 1 d . . . C5 C 0.90583(14) -0.2229(2) 0.04987(9) 0.0460(4) Uani 1 1 d . . . H5 H 0.9626 -0.1566 0.0264 0.055 Uiso 1 1 calc R . . C6 C 0.85727(14) -0.3779(2) 0.01280(9) 0.0464(4) Uani 1 1 d . . . H6 H 0.8803 -0.4181 -0.0361 0.056 Uiso 1 1 calc R . . C7 C 0.92005(14) 0.0070(2) 0.16047(9) 0.0457(4) Uani 1 1 d . . . C8 C 0.71572(17) -0.6351(2) 0.00446(11) 0.0550(5) Uani 1 1 d . . . O9 O 0.88482(11) 0.06867(15) 0.21929(6) 0.0567(4) Uani 1 1 d . . . O10 O 1.00228(11) 0.08224(17) 0.12523(7) 0.0599(4) Uani 1 1 d . . . H10 H 1.0240(18) 0.198(3) 0.1441(12) 0.072 Uiso 1 1 d . . . C14 C 1.07633(14) 0.4626(2) 0.23917(9) 0.0450(4) Uani 1 1 d . . . C15 C 1.15021(16) 0.6282(2) 0.26050(11) 0.0553(5) Uani 1 1 d . . . H15A H 1.1389 0.7001 0.2094 0.066 Uiso 1 1 calc R . . H15B H 1.2411 0.5984 0.2788 0.066 Uiso 1 1 calc R . . C16 C 1.11343(17) 0.7370(2) 0.32837(9) 0.0561(5) Uani 1 1 d . . . H16A H 1.1807 0.8231 0.3506 0.067 Uiso 1 1 calc R . . H16B H 1.0343 0.8015 0.3046 0.067 Uiso 1 1 calc R . . C17 C 1.09467(17) 0.6192(2) 0.39792(10) 0.0595(5) Uani 1 1 d . . . H17A H 1.1738 0.5544 0.4215 0.071 Uiso 1 1 calc R . . H17B H 1.0739 0.6903 0.4431 0.071 Uiso 1 1 calc R . . C18 C 0.98894(16) 0.4920(2) 0.36486(10) 0.0547(5) Uani 1 1 d . . . H18A H 0.9854 0.4043 0.4084 0.066 Uiso 1 1 calc R . . H18B H 0.9073 0.5553 0.3513 0.066 Uiso 1 1 calc R . . N19 N 1.00778(13) 0.40319(19) 0.28980(8) 0.0484(4) Uani 1 1 d . . . H19 H 0.9678(17) 0.304(3) 0.2748(11) 0.058 Uiso 1 1 d . . . O20 O 1.08339(11) 0.38088(15) 0.17462(7) 0.0567(4) Uani 1 1 d . . . F11 F 0.7040(6) -0.7658(9) 0.0538(4) 0.0761(14) Uani 0.60 1 d P A 1 F12 F 0.7739(5) -0.7008(6) -0.0497(2) 0.0804(14) Uani 0.60 1 d P A 1 F13 F 0.5979(4) -0.6066(9) -0.0391(4) 0.0893(18) Uani 0.60 1 d P A 1 F11' F 0.7955(10) -0.7253(14) -0.0277(7) 0.167(5) Uani 0.40 1 d P A 2 F12' F 0.6165(9) -0.6026(14) -0.0533(7) 0.135(4) Uani 0.40 1 d P A 2 F13' F 0.6815(11) -0.7442(14) 0.0575(7) 0.115(4) Uani 0.40 1 d P A 2 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 C1 0.0437(8) 0.0496(9) 0.0444(8) 0.0084(7) 0.0128(6) 0.0039(7) C2 0.0486(9) 0.0585(11) 0.0485(9) 0.0099(7) 0.0212(7) -0.0021(8) C3 0.0479(9) 0.0602(11) 0.0407(8) 0.0041(7) 0.0194(7) 0.0045(7) C4 0.0384(8) 0.0531(9) 0.0376(8) 0.0043(7) 0.0118(6) 0.0051(7) C5 0.0434(8) 0.0560(10) 0.0424(8) 0.0029(7) 0.0177(6) -0.0018(7) C6 0.0471(9) 0.0548(10) 0.0405(8) 0.0009(7) 0.0169(7) 0.0019(7) C7 0.0445(8) 0.0551(10) 0.0401(8) 0.0041(7) 0.0155(7) 0.0029(7) C8 0.0598(11) 0.0523(10) 0.0566(11) 0.0074(8) 0.0211(9) -0.0034(9) O9 0.0679(8) 0.0611(8) 0.0497(7) -0.0063(5) 0.0310(6) -0.0024(6) O10 0.0647(8) 0.0647(8) 0.0603(7) -0.0161(6) 0.0347(6) -0.0175(6) C14 0.0417(8) 0.0500(9) 0.0441(9) 0.0011(7) 0.0118(7) 0.0049(7) C15 0.0547(10) 0.0595(10) 0.0536(9) -0.0037(8) 0.0166(7) -0.0067(8) C16 0.0591(11) 0.0529(10) 0.0552(9) -0.0053(8) 0.0111(8) -0.0042(8) C17 0.0687(12) 0.0625(11) 0.0471(9) -0.0085(8) 0.0131(8) -0.0027(9) C18 0.0647(11) 0.0570(10) 0.0469(9) -0.0054(7) 0.0222(8) -0.0010(8) N19 0.0516(8) 0.0501(8) 0.0469(7) -0.0049(6) 0.0185(6) -0.0019(6) O20 0.0640(7) 0.0599(7) 0.0528(7) -0.0093(5) 0.0270(5) -0.0072(6) F11 0.105(2) 0.056(2) 0.067(2) 0.0173(16) 0.0181(18) -0.0020(16) F12 0.108(3) 0.072(2) 0.0839(14) -0.0345(12) 0.0678(17) -0.040(2) F13 0.0547(17) 0.071(3) 0.125(4) -0.012(3) -0.012(2) 0.0008(15) F11' 0.105(5) 0.103(5) 0.308(12) -0.097(7) 0.078(7) -0.008(4) F12' 0.198(10) 0.066(4) 0.090(4) 0.018(3) -0.067(5) -0.042(5) F13' 0.185(8) 0.075(5) 0.107(5) -0.012(3) 0.079(5) -0.073(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 C1 C2 1.389(2) . ? C1 C6 1.389(2) . ? C1 C8 1.487(2) . ? C2 C3 1.379(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.394(2) . ? C4 C7 1.493(2) . ? C5 C6 1.382(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O9 1.2182(18) . ? C7 O10 1.3094(18) . ? C8 F12' 1.284(9) . ? C8 F12 1.310(4) . ? C8 F11 1.315(6) . ? C8 F11' 1.315(10) . ? C8 F13' 1.325(10) . ? C8 F13 1.332(5) . ? O10 H10 0.95(2) . ? C14 O20 1.2520(18) . ? C14 N19 1.324(2) . ? C14 C15 1.498(2) . ? C15 C16 1.522(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.509(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.508(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N19 1.467(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N19 H19 0.88(2) . ? 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 C1 C6 120.31(15) . . ? C2 C1 C8 120.18(14) . . ? C6 C1 C8 119.42(14) . . ? C3 C2 C1 119.75(14) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.54(14) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.46(15) . . ? C3 C4 C7 119.58(13) . . ? C5 C4 C7 120.96(14) . . ? C6 C5 C4 120.38(14) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 119.55(14) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? O9 C7 O10 123.90(15) . . ? O9 C7 C4 122.46(14) . . ? O10 C7 C4 113.65(13) . . ? F12' C8 F12 91.6(6) . . ? F12' C8 F11 114.8(6) . . ? F12 C8 F11 105.1(4) . . ? F12' C8 F11' 108.9(7) . . ? F12 C8 F11' 18.7(7) . . ? F11 C8 F11' 91.0(6) . . ? F12' C8 F13' 107.0(7) . . ? F12 C8 F13' 117.6(6) . . ? F11 C8 F13' 13.6(9) . . ? F11' C8 F13' 104.4(8) . . ? F12' C8 F13 15.0(8) . . ? F12 C8 F13 104.8(4) . . ? F11 C8 F13 103.7(4) . . ? F11' C8 F13 120.8(6) . . ? F13' C8 F13 94.2(6) . . ? F12' C8 C1 112.7(5) . . ? F12 C8 C1 114.8(2) . . ? F11 C8 C1 115.3(3) . . ? F11' C8 C1 112.1(5) . . ? F13' C8 C1 111.3(5) . . ? F13 C8 C1 112.0(3) . . ? C7 O10 H10 114.2(12) . . ? O20 C14 N19 121.29(15) . . ? O20 C14 C15 119.07(13) . . ? N19 C14 C15 119.62(14) . . ? C14 C15 C16 114.61(14) . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C17 C16 C15 109.65(15) . . ? C17 C16 H16A 109.7 . . ? C15 C16 H16A 109.7 . . ? C17 C16 H16B 109.7 . . ? C15 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? C18 C17 C16 109.88(13) . . ? C18 C17 H17A 109.7 . . ? C16 C17 H17A 109.7 . . ? C18 C17 H17B 109.7 . . ? C16 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? N19 C18 C17 110.96(13) . . ? N19 C18 H18A 109.4 . . ? C17 C18 H18A 109.4 . . ? N19 C18 H18B 109.4 . . ? C17 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C14 N19 C18 125.64(15) . . ? C14 N19 H19 115.7(11) . . ? C18 N19 H19 118.6(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 C6 C1 C2 C3 0.8(2) . . . . ? C8 C1 C2 C3 -175.92(15) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? C2 C3 C4 C5 -1.4(2) . . . . ? C2 C3 C4 C7 177.76(14) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C7 C4 C5 C6 -177.81(14) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C2 C1 C6 C5 -0.8(2) . . . . ? C8 C1 C6 C5 175.88(14) . . . . ? C3 C4 C7 O9 -4.8(2) . . . . ? C5 C4 C7 O9 174.40(14) . . . . ? C3 C4 C7 O10 175.51(14) . . . . ? C5 C4 C7 O10 -5.3(2) . . . . ? C2 C1 C8 F12' 92.9(6) . . . . ? C6 C1 C8 F12' -83.9(6) . . . . ? C2 C1 C8 F12 -164.1(3) . . . . ? C6 C1 C8 F12 19.2(3) . . . . ? C2 C1 C8 F11 -41.6(4) . . . . ? C6 C1 C8 F11 141.7(4) . . . . ? C2 C1 C8 F11' -143.9(6) . . . . ? C6 C1 C8 F11' 39.4(6) . . . . ? C2 C1 C8 F13' -27.4(6) . . . . ? C6 C1 C8 F13' 155.9(6) . . . . ? C2 C1 C8 F13 76.6(4) . . . . ? C6 C1 C8 F13 -100.1(4) . . . . ? O20 C14 C15 C16 167.26(15) . . . . ? N19 C14 C15 C16 -14.5(2) . . . . ? C14 C15 C16 C17 42.74(19) . . . . ? C15 C16 C17 C18 -61.45(19) . . . . ? C16 C17 C18 N19 50.8(2) . . . . ? O20 C14 N19 C18 -177.32(15) . . . . ? C15 C14 N19 C18 4.5(2) . . . . ? C17 C18 N19 C14 -23.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.153 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.038 # Attachment '6071_web_deposit_cif_file_3_AuroraJ.Cruz-Cabeza_1309426426.2h.cif' data_2h _database_code_depnum_ccdc_archive 'CCDC 832271' #TrackingRef '6071_web_deposit_cif_file_3_AuroraJ.Cruz-Cabeza_1309426426.2h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 N O4, C5 H9 N O' _chemical_formula_sum 'C12 H14 N2 O5' _chemical_formula_weight 266.25 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6109(1) _cell_length_b 6.9719(2) _cell_length_c 13.9678(3) _cell_angle_alpha 93.855(1) _cell_angle_beta 97.257(1) _cell_angle_gamma 101.429(1) _cell_volume 623.14(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6626 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 29.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 10652 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 29.11 _reflns_number_total 3314 _reflns_number_gt 2733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0549P)^2^+0.2132P] 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_number_reflns 3314 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _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 C1 C 0.7239(2) 0.5238(2) 0.17934(10) 0.0369(3) Uani 1 1 d . . . H1A H 0.8223 0.4986 0.2343 0.044 Uiso 1 1 calc R . . H1B H 0.6119 0.4046 0.1626 0.044 Uiso 1 1 calc R . . C2 C 0.6303(3) 0.6943(2) 0.20969(11) 0.0425(3) Uani 1 1 d . . . H2A H 0.5332 0.6536 0.2566 0.051 Uiso 1 1 calc R . . H2B H 0.7423 0.8034 0.2424 0.051 Uiso 1 1 calc R . . C3 C 0.5151(3) 0.7645(3) 0.12388(12) 0.0466(4) Uani 1 1 d . . . H3A H 0.4542 0.8759 0.1456 0.056 Uiso 1 1 calc R . . H3B H 0.3997 0.6571 0.0924 0.056 Uiso 1 1 calc R . . C4 C 0.6637(2) 0.8301(2) 0.05094(10) 0.0368(3) Uani 1 1 d . . . H4A H 0.5799 0.8390 -0.0119 0.044 Uiso 1 1 calc R . . H4B H 0.7463 0.9634 0.0741 0.044 Uiso 1 1 calc R . . C5 C 0.8110(2) 0.69618(19) 0.03486(9) 0.0311(3) Uani 1 1 d . . . N6 N 0.8343(2) 0.56247(17) 0.09576(8) 0.0347(3) Uani 1 1 d . . . H6 H 0.9251 0.4895 0.0851 0.042 Uiso 1 1 calc R . . O7 O 0.91272(18) 0.71205(15) -0.03554(7) 0.0409(3) Uani 1 1 d . . . C8 C 0.24003(18) 0.86116(17) 0.50543(8) 0.0245(2) Uani 1 1 d . . . C9 C 0.26144(19) 1.06292(18) 0.52048(9) 0.0261(2) Uani 1 1 d . . . H9 H 0.2871 1.1278 0.5842 0.031 Uiso 1 1 calc R . . C10 C 0.24444(19) 1.16742(17) 0.44003(9) 0.0265(2) Uani 1 1 d . . . H10 H 0.2587 1.3060 0.4483 0.032 Uiso 1 1 calc R . . C11 C 0.20652(18) 1.07049(17) 0.34695(8) 0.0245(2) Uani 1 1 d . . . C12 C 0.1873(2) 0.86743(18) 0.33414(9) 0.0268(2) Uani 1 1 d . . . H12 H 0.1629 0.8020 0.2706 0.032 Uiso 1 1 calc R . . C13 C 0.20352(19) 0.76053(17) 0.41396(9) 0.0272(2) Uani 1 1 d . . . H13 H 0.1900 0.6220 0.4061 0.033 Uiso 1 1 calc R . . N14 N 0.25958(17) 0.74951(16) 0.59103(8) 0.0304(2) Uani 1 1 d . . . O15 O 0.28903(19) 0.83993(16) 0.67139(7) 0.0428(3) Uani 1 1 d . . . O16 O 0.2470(2) 0.57217(15) 0.57768(8) 0.0484(3) Uani 1 1 d . . . C17 C 0.1840(2) 1.19007(18) 0.26205(9) 0.0280(3) Uani 1 1 d . . . O18 O 0.1900(2) 1.36498(14) 0.27184(7) 0.0435(3) Uani 1 1 d . . . O19 O 0.15673(18) 1.08460(14) 0.17780(7) 0.0376(2) Uani 1 1 d . . . H19 H 0.137(3) 1.170(3) 0.1264(13) 0.045 Uiso 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 C1 0.0494(8) 0.0377(7) 0.0269(6) 0.0089(5) 0.0119(6) 0.0113(6) C2 0.0495(9) 0.0487(8) 0.0346(7) 0.0046(6) 0.0173(6) 0.0152(7) C3 0.0477(9) 0.0549(9) 0.0435(8) 0.0054(7) 0.0110(7) 0.0231(7) C4 0.0482(8) 0.0372(7) 0.0315(7) 0.0067(5) 0.0067(6) 0.0222(6) C5 0.0449(7) 0.0306(6) 0.0219(5) 0.0046(4) 0.0063(5) 0.0163(5) N6 0.0516(7) 0.0345(6) 0.0269(5) 0.0108(4) 0.0140(5) 0.0226(5) O7 0.0646(7) 0.0429(6) 0.0275(5) 0.0148(4) 0.0183(5) 0.0295(5) C8 0.0234(5) 0.0281(6) 0.0238(5) 0.0067(4) 0.0055(4) 0.0068(4) C9 0.0267(6) 0.0288(6) 0.0235(5) 0.0008(4) 0.0051(4) 0.0071(4) C10 0.0287(6) 0.0239(5) 0.0285(6) 0.0030(4) 0.0065(5) 0.0080(4) C11 0.0255(5) 0.0250(5) 0.0252(6) 0.0048(4) 0.0064(4) 0.0079(4) C12 0.0311(6) 0.0258(6) 0.0240(5) 0.0021(4) 0.0046(5) 0.0070(4) C13 0.0311(6) 0.0226(5) 0.0283(6) 0.0037(4) 0.0049(5) 0.0059(4) N14 0.0335(6) 0.0322(5) 0.0272(5) 0.0081(4) 0.0069(4) 0.0077(4) O15 0.0621(7) 0.0432(6) 0.0245(5) 0.0061(4) 0.0067(4) 0.0128(5) O16 0.0810(8) 0.0297(5) 0.0366(6) 0.0110(4) 0.0084(5) 0.0143(5) C17 0.0319(6) 0.0269(6) 0.0282(6) 0.0070(4) 0.0082(5) 0.0093(5) O18 0.0713(8) 0.0274(5) 0.0360(5) 0.0083(4) 0.0104(5) 0.0165(5) O19 0.0608(7) 0.0323(5) 0.0241(4) 0.0074(4) 0.0073(4) 0.0183(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 C1 N6 1.4656(16) . ? C1 C2 1.505(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.501(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.533(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5030(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O7 1.2584(15) . ? C5 N6 1.3216(16) . ? N6 H6 0.8800 . ? C8 C9 1.3844(17) . ? C8 C13 1.3847(17) . ? C8 N14 1.4758(15) . ? C9 C10 1.3844(17) . ? C9 H9 0.9500 . ? C10 C11 1.3936(16) . ? C10 H10 0.9500 . ? C11 C12 1.3933(16) . ? C11 C17 1.5036(16) . ? C12 C13 1.3868(16) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? N14 O16 1.2225(15) . ? N14 O15 1.2233(15) . ? C17 O18 1.2102(15) . ? C17 O19 1.3174(15) . ? O19 H19 0.977(18) . ? 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 N6 C1 C2 111.54(11) . . ? N6 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N6 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C3 C2 C1 111.10(12) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 110.13(13) . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 114.31(11) . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? O7 C5 N6 120.19(12) . . ? O7 C5 C4 120.35(11) . . ? N6 C5 C4 119.46(11) . . ? C5 N6 C1 126.40(11) . . ? C5 N6 H6 116.8 . . ? C1 N6 H6 116.8 . . ? C9 C8 C13 122.94(11) . . ? C9 C8 N14 118.23(10) . . ? C13 C8 N14 118.82(10) . . ? C10 C9 C8 118.10(11) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? C9 C10 C11 120.40(11) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.15(11) . . ? C12 C11 C17 121.52(11) . . ? C10 C11 C17 118.32(10) . . ? C13 C12 C11 120.16(11) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C8 C13 C12 118.23(11) . . ? C8 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? O16 N14 O15 123.67(11) . . ? O16 N14 C8 118.21(11) . . ? O15 N14 C8 118.11(11) . . ? O18 C17 O19 124.51(11) . . ? O18 C17 C11 122.44(11) . . ? O19 C17 C11 113.05(10) . . ? C17 O19 H19 108.5(10) . . ? 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 N6 C1 C2 C3 47.30(18) . . . . ? C1 C2 C3 C4 -59.65(18) . . . . ? C2 C3 C4 C5 42.34(19) . . . . ? C3 C4 C5 O7 166.59(14) . . . . ? C3 C4 C5 N6 -14.0(2) . . . . ? O7 C5 N6 C1 -178.56(14) . . . . ? C4 C5 N6 C1 2.0(2) . . . . ? C2 C1 N6 C5 -18.8(2) . . . . ? C13 C8 C9 C10 0.29(18) . . . . ? N14 C8 C9 C10 179.57(11) . . . . ? C8 C9 C10 C11 0.09(17) . . . . ? C9 C10 C11 C12 -0.58(18) . . . . ? C9 C10 C11 C17 178.49(11) . . . . ? C10 C11 C12 C13 0.69(18) . . . . ? C17 C11 C12 C13 -178.35(11) . . . . ? C9 C8 C13 C12 -0.18(18) . . . . ? N14 C8 C13 C12 -179.46(11) . . . . ? C11 C12 C13 C8 -0.31(18) . . . . ? C9 C8 N14 O16 -177.82(12) . . . . ? C13 C8 N14 O16 1.49(17) . . . . ? C9 C8 N14 O15 1.66(17) . . . . ? C13 C8 N14 O15 -179.04(11) . . . . ? C12 C11 C17 O18 176.25(13) . . . . ? C10 C11 C17 O18 -2.80(19) . . . . ? C12 C11 C17 O19 -3.44(17) . . . . ? C10 C11 C17 O19 177.51(11) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.536 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.042 # Attachment '6072_web_deposit_cif_file_4_AuroraJ.Cruz-Cabeza_1309426426.2k.cif' data_2k _database_code_depnum_ccdc_archive 'CCDC 832272' #TrackingRef '6072_web_deposit_cif_file_4_AuroraJ.Cruz-Cabeza_1309426426.2k.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 N2 O6, C5 H9 N O' _chemical_formula_sum 'C12 H13 N3 O7' _chemical_formula_weight 311.25 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4022(1) _cell_length_b 13.3198(3) _cell_length_c 15.1641(3) _cell_angle_alpha 109.418(1) _cell_angle_beta 93.784(1) _cell_angle_gamma 104.670(1) _cell_volume 1345.49(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9939 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -COOH hydrogen atoms were located and their positions were refineed satisfactorily. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 17994 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 25.39 _reflns_number_total 4893 _reflns_number_gt 3696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0682P)^2^+1.4061P] 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_number_reflns 4893 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 C1 C 0.0475(4) 0.3473(2) -0.00438(18) 0.0324(6) Uani 1 1 d . . . C2 C 0.1037(4) 0.2451(2) -0.0093(2) 0.0417(7) Uani 1 1 d . . . H2A H 0.1596 0.2548 0.0552 0.050 Uiso 1 1 calc R . . H2B H 0.2032 0.2386 -0.0496 0.050 Uiso 1 1 calc R . . C3 C -0.0568(5) 0.1375(3) -0.0480(3) 0.0698(11) Uani 1 1 d . . . H3A H -0.0655 0.1054 -0.1177 0.084 Uiso 1 1 calc R . . H3B H -0.0271 0.0838 -0.0215 0.084 Uiso 1 1 calc R . . C4 C -0.2379(6) 0.1513(3) -0.0263(4) 0.0778(13) Uani 1 1 d . . . H4A H -0.2354 0.1714 0.0429 0.093 Uiso 1 1 calc R . . H4B H -0.3366 0.0792 -0.0583 0.093 Uiso 1 1 calc R . . C5 C -0.2918(4) 0.2376(2) -0.0553(2) 0.0420(7) Uani 1 1 d . . . H5A H -0.3339 0.2079 -0.1248 0.050 Uiso 1 1 calc R . . H5B H -0.3989 0.2559 -0.0243 0.050 Uiso 1 1 calc R . . N6 N -0.1319(3) 0.33884(18) -0.02901(15) 0.0343(5) Uani 1 1 d . . . H6 H -0.1578 0.3996 -0.0297 0.041 Uiso 1 1 calc R . . O7 O 0.1715(3) 0.44017(15) 0.02268(13) 0.0378(5) Uani 1 1 d . . . C8 C -0.1478(4) 0.1694(2) 0.4127(2) 0.0394(7) Uani 1 1 d . . . C9 C -0.2577(5) 0.0508(2) 0.3928(2) 0.0490(8) Uani 1 1 d . . . H9A H -0.3646 0.0502 0.4288 0.059 Uiso 1 1 calc R . . H9B H -0.1745 0.0146 0.4167 0.059 Uiso 1 1 calc R . . C10 C -0.3356(7) -0.0176(3) 0.2891(3) 0.0804(14) Uani 1 1 d . . . H10A H -0.3531 -0.0970 0.2791 0.097 Uiso 1 1 calc R . . H10B H -0.4620 -0.0092 0.2744 0.097 Uiso 1 1 calc R . . C11 C -0.2225(8) 0.0102(3) 0.2240(3) 0.0833(14) Uani 1 1 d . . . H11A H -0.2951 -0.0307 0.1591 0.100 Uiso 1 1 calc R . . H11B H -0.1090 -0.0156 0.2277 0.100 Uiso 1 1 calc R . . C12 C -0.1593(5) 0.1315(2) 0.2397(2) 0.0438(7) Uani 1 1 d . . . H12A H -0.0504 0.1466 0.2067 0.053 Uiso 1 1 calc R . . H12B H -0.2634 0.1516 0.2118 0.053 Uiso 1 1 calc R . . N13 N -0.1041(3) 0.20120(19) 0.34079(17) 0.0386(6) Uani 1 1 d . . . H13 H -0.0355 0.2706 0.3549 0.046 Uiso 1 1 calc R . . O14 O -0.0969(3) 0.23609(17) 0.49708(15) 0.0513(6) Uani 1 1 d . . . C15 C 0.3499(4) 0.5809(2) 0.55454(18) 0.0305(6) Uani 1 1 d . . . C16 C 0.4360(4) 0.6331(2) 0.49565(19) 0.0319(6) Uani 1 1 d . . . H16 H 0.4009 0.5993 0.4287 0.038 Uiso 1 1 calc R . . C17 C 0.5728(4) 0.7346(2) 0.53639(19) 0.0323(6) Uani 1 1 d . . . C18 C 0.6273(4) 0.7874(2) 0.6335(2) 0.0342(6) Uani 1 1 d . . . H18 H 0.7198 0.8581 0.6605 0.041 Uiso 1 1 calc R . . C19 C 0.5411(4) 0.7326(2) 0.68919(19) 0.0327(6) Uani 1 1 d . . . C20 C 0.4037(4) 0.6303(2) 0.65205(19) 0.0320(6) Uani 1 1 d . . . H20 H 0.3476 0.5947 0.6926 0.038 Uiso 1 1 calc R . . N21 N 0.5960(4) 0.7856(2) 0.79318(17) 0.0403(6) Uani 1 1 d . . . O22 O 0.7288(3) 0.87060(19) 0.82489(16) 0.0597(7) Uani 1 1 d . . . O23 O 0.5047(3) 0.74229(19) 0.84223(14) 0.0519(6) Uani 1 1 d . . . N24 N 0.6661(3) 0.7883(2) 0.47396(18) 0.0395(6) Uani 1 1 d . . . O25 O 0.7804(4) 0.88018(19) 0.51145(17) 0.0623(7) Uani 1 1 d . . . O26 O 0.6252(3) 0.73775(18) 0.38836(15) 0.0477(5) Uani 1 1 d . . . C27 C 0.2011(4) 0.4708(2) 0.50960(18) 0.0310(6) Uani 1 1 d . . . O28 O 0.1396(3) 0.43377(16) 0.42499(13) 0.0416(5) Uani 1 1 d . . . O29 O 0.1482(3) 0.42155(17) 0.56868(14) 0.0393(5) Uani 1 1 d . . . H29 H 0.070(5) 0.358(3) 0.542(2) 0.047 Uiso 1 1 d . . . C30 C 0.7943(4) 0.5983(2) 0.19485(18) 0.0321(6) Uani 1 1 d . . . C31 C 0.8697(4) 0.5122(2) 0.19362(17) 0.0317(6) Uani 1 1 d . . . H31 H 0.7956 0.4367 0.1639 0.038 Uiso 1 1 calc R . . C32 C 1.0547(4) 0.5392(2) 0.23657(17) 0.0309(6) Uani 1 1 d . . . C33 C 1.1694(4) 0.6473(2) 0.28121(17) 0.0319(6) Uani 1 1 d . . . H33 H 1.2972 0.6640 0.3093 0.038 Uiso 1 1 calc R . . C34 C 1.0862(4) 0.7298(2) 0.28232(18) 0.0343(6) Uani 1 1 d . . . C35 C 0.9029(4) 0.7079(2) 0.24077(18) 0.0346(6) Uani 1 1 d . . . H35 H 0.8514 0.7671 0.2435 0.041 Uiso 1 1 calc R . . N36 N 1.2033(4) 0.8465(2) 0.32967(18) 0.0425(6) Uani 1 1 d . . . O37 O 1.3513(3) 0.86589(18) 0.38079(16) 0.0517(6) Uani 1 1 d . . . O38 O 1.1471(4) 0.91780(19) 0.3126(2) 0.0756(8) Uani 1 1 d . . . N39 N 1.1362(4) 0.44860(19) 0.23512(15) 0.0363(5) Uani 1 1 d . . . O40 O 1.3064(3) 0.47180(17) 0.25984(14) 0.0436(5) Uani 1 1 d . . . O41 O 1.0266(3) 0.35388(16) 0.20840(15) 0.0497(6) Uani 1 1 d . . . C42 C 0.5977(4) 0.5755(2) 0.14595(18) 0.0344(6) Uani 1 1 d . . . O43 O 0.5266(3) 0.64952(17) 0.15170(15) 0.0467(5) Uani 1 1 d . . . O44 O 0.5170(3) 0.46933(16) 0.09656(15) 0.0390(5) Uani 1 1 d . . . H44 H 0.421(5) 0.462(3) 0.071(2) 0.047 Uiso 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 C1 0.0332(15) 0.0358(14) 0.0239(12) 0.0090(11) 0.0021(11) 0.0060(12) C2 0.0421(17) 0.0393(16) 0.0435(16) 0.0141(13) 0.0021(13) 0.0142(13) C3 0.053(2) 0.0377(18) 0.111(3) 0.023(2) 0.002(2) 0.0089(16) C4 0.055(2) 0.052(2) 0.121(4) 0.040(2) -0.001(2) -0.0002(18) C5 0.0338(16) 0.0364(15) 0.0464(17) 0.0119(13) 0.0007(13) 0.0002(12) N6 0.0324(13) 0.0322(12) 0.0342(12) 0.0111(10) 0.0009(10) 0.0048(10) O7 0.0318(11) 0.0363(10) 0.0383(10) 0.0117(8) -0.0007(8) 0.0021(8) C8 0.0361(16) 0.0365(15) 0.0445(17) 0.0167(13) 0.0045(13) 0.0067(12) C9 0.052(2) 0.0369(16) 0.0510(18) 0.0187(14) 0.0060(15) -0.0021(14) C10 0.118(4) 0.0409(19) 0.055(2) 0.0055(17) 0.025(2) -0.011(2) C11 0.124(4) 0.049(2) 0.053(2) 0.0145(18) -0.002(2) -0.007(2) C12 0.0454(18) 0.0427(16) 0.0409(16) 0.0156(13) 0.0053(14) 0.0088(13) N13 0.0384(14) 0.0316(12) 0.0442(14) 0.0169(11) 0.0032(11) 0.0041(10) O14 0.0614(15) 0.0386(11) 0.0413(12) 0.0131(10) 0.0078(10) -0.0049(10) C15 0.0286(14) 0.0320(13) 0.0330(14) 0.0125(11) 0.0044(11) 0.0114(11) C16 0.0318(15) 0.0333(14) 0.0328(14) 0.0125(11) 0.0047(11) 0.0127(11) C17 0.0289(14) 0.0345(14) 0.0385(14) 0.0180(12) 0.0054(11) 0.0116(11) C18 0.0288(14) 0.0294(13) 0.0425(15) 0.0119(12) 0.0036(12) 0.0071(11) C19 0.0300(14) 0.0374(14) 0.0317(14) 0.0110(11) 0.0028(11) 0.0142(11) C20 0.0315(14) 0.0336(14) 0.0340(14) 0.0139(11) 0.0071(11) 0.0120(11) N21 0.0388(14) 0.0399(14) 0.0375(13) 0.0091(11) 0.0020(11) 0.0111(11) O22 0.0581(15) 0.0501(13) 0.0451(13) 0.0040(11) -0.0025(11) -0.0072(12) O23 0.0573(15) 0.0576(14) 0.0354(11) 0.0164(10) 0.0073(10) 0.0082(11) N24 0.0359(14) 0.0408(14) 0.0462(15) 0.0228(12) 0.0069(11) 0.0094(11) O25 0.0690(17) 0.0456(13) 0.0603(14) 0.0242(11) 0.0078(13) -0.0098(12) O26 0.0442(13) 0.0588(13) 0.0421(12) 0.0255(11) 0.0073(10) 0.0084(10) C27 0.0297(14) 0.0338(14) 0.0337(15) 0.0150(12) 0.0072(11) 0.0120(11) O28 0.0466(12) 0.0379(11) 0.0329(11) 0.0137(9) 0.0004(9) -0.0002(9) O29 0.0429(12) 0.0349(10) 0.0358(11) 0.0148(9) 0.0052(9) 0.0016(9) C30 0.0328(15) 0.0361(14) 0.0258(13) 0.0108(11) 0.0073(11) 0.0072(11) C31 0.0359(15) 0.0315(13) 0.0232(12) 0.0093(10) 0.0050(11) 0.0028(11) C32 0.0362(15) 0.0339(14) 0.0246(12) 0.0131(11) 0.0068(11) 0.0097(11) C33 0.0316(14) 0.0376(14) 0.0245(13) 0.0118(11) 0.0048(11) 0.0061(11) C34 0.0360(16) 0.0322(14) 0.0287(13) 0.0088(11) 0.0039(11) 0.0031(12) C35 0.0377(16) 0.0327(14) 0.0312(14) 0.0093(11) 0.0065(12) 0.0097(12) N36 0.0447(16) 0.0326(13) 0.0409(14) 0.0077(11) 0.0022(12) 0.0042(11) O37 0.0396(13) 0.0457(12) 0.0528(13) 0.0105(10) -0.0040(11) -0.0039(10) O38 0.0800(19) 0.0323(12) 0.095(2) 0.0129(13) -0.0242(16) 0.0075(12) N39 0.0462(16) 0.0374(13) 0.0272(11) 0.0134(10) 0.0054(10) 0.0133(11) O40 0.0420(13) 0.0541(12) 0.0435(11) 0.0244(10) 0.0085(10) 0.0198(10) O41 0.0642(15) 0.0320(11) 0.0471(12) 0.0133(9) -0.0043(11) 0.0090(10) C42 0.0327(15) 0.0398(16) 0.0299(14) 0.0136(12) 0.0065(11) 0.0075(12) O43 0.0403(12) 0.0455(12) 0.0509(12) 0.0134(10) -0.0015(10) 0.0146(10) O44 0.0283(11) 0.0403(11) 0.0421(11) 0.0133(9) -0.0021(9) 0.0034(9) _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 C1 O7 1.257(3) . ? C1 N6 1.321(4) . ? C1 C2 1.501(4) . ? C2 C3 1.515(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.443(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.490(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N6 1.466(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? N6 H6 0.8800 . ? C8 O14 1.256(4) . ? C8 N13 1.326(4) . ? C8 C9 1.499(4) . ? C9 C10 1.516(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.417(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.494(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N13 1.469(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? N13 H13 0.8800 . ? C15 C20 1.386(4) . ? C15 C16 1.396(4) . ? C15 C27 1.499(4) . ? C16 C17 1.380(4) . ? C16 H16 0.9500 . ? C17 C18 1.384(4) . ? C17 N24 1.474(4) . ? C18 C19 1.377(4) . ? C18 H18 0.9500 . ? C19 C20 1.386(4) . ? C19 N21 1.477(4) . ? C20 H20 0.9500 . ? N21 O22 1.221(3) . ? N21 O23 1.224(3) . ? N24 O25 1.219(3) . ? N24 O26 1.222(3) . ? C27 O28 1.219(3) . ? C27 O29 1.302(3) . ? O29 H29 0.84(3) . ? C30 C35 1.385(4) . ? C30 C31 1.392(4) . ? C30 C42 1.498(4) . ? C31 C32 1.381(4) . ? C31 H31 0.9500 . ? C32 C33 1.382(4) . ? C32 N39 1.474(4) . ? C33 C34 1.385(4) . ? C33 H33 0.9500 . ? C34 C35 1.374(4) . ? C34 N36 1.475(3) . ? C35 H35 0.9500 . ? N36 O37 1.216(3) . ? N36 O38 1.221(3) . ? N39 O40 1.219(3) . ? N39 O41 1.230(3) . ? C42 O43 1.212(3) . ? C42 O44 1.314(3) . ? O44 H44 0.75(4) . ? 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 O7 C1 N6 120.5(3) . . ? O7 C1 C2 119.8(3) . . ? N6 C1 C2 119.8(2) . . ? C1 C2 C3 114.7(3) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 113.5(3) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C3 C4 C5 114.2(3) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? N6 C5 C4 111.0(3) . . ? N6 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? N6 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C1 N6 C5 126.0(2) . . ? C1 N6 H6 117.0 . . ? C5 N6 H6 117.0 . . ? O14 C8 N13 121.5(3) . . ? O14 C8 C9 119.4(3) . . ? N13 C8 C9 119.2(3) . . ? C8 C9 C10 114.7(3) . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 115.5(3) . . ? C11 C10 H10A 108.4 . . ? C9 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C9 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C12 114.8(4) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.5 . . ? N13 C12 C11 112.2(3) . . ? N13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? N13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C8 N13 C12 126.2(2) . . ? C8 N13 H13 116.9 . . ? C12 N13 H13 116.9 . . ? C20 C15 C16 120.1(2) . . ? C20 C15 C27 121.5(2) . . ? C16 C15 C27 118.4(2) . . ? C17 C16 C15 118.8(2) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 122.6(2) . . ? C16 C17 N24 118.7(2) . . ? C18 C17 N24 118.7(2) . . ? C19 C18 C17 116.8(2) . . ? C19 C18 H18 121.6 . . ? C17 C18 H18 121.6 . . ? C18 C19 C20 123.0(2) . . ? C18 C19 N21 118.6(2) . . ? C20 C19 N21 118.4(2) . . ? C15 C20 C19 118.6(2) . . ? C15 C20 H20 120.7 . . ? C19 C20 H20 120.7 . . ? O22 N21 O23 124.1(2) . . ? O22 N21 C19 117.9(2) . . ? O23 N21 C19 118.0(2) . . ? O25 N24 O26 124.4(2) . . ? O25 N24 C17 117.6(2) . . ? O26 N24 C17 118.0(2) . . ? O28 C27 O29 125.0(2) . . ? O28 C27 C15 121.0(2) . . ? O29 C27 C15 113.9(2) . . ? C27 O29 H29 113(2) . . ? C35 C30 C31 119.9(3) . . ? C35 C30 C42 118.6(2) . . ? C31 C30 C42 121.5(2) . . ? C32 C31 C30 118.5(2) . . ? C32 C31 H31 120.8 . . ? C30 C31 H31 120.8 . . ? C31 C32 C33 123.5(3) . . ? C31 C32 N39 118.9(2) . . ? C33 C32 N39 117.6(2) . . ? C32 C33 C34 115.7(3) . . ? C32 C33 H33 122.1 . . ? C34 C33 H33 122.1 . . ? C35 C34 C33 123.3(2) . . ? C35 C34 N36 119.2(3) . . ? C33 C34 N36 117.5(3) . . ? C34 C35 C30 119.1(3) . . ? C34 C35 H35 120.4 . . ? C30 C35 H35 120.4 . . ? O37 N36 O38 124.0(3) . . ? O37 N36 C34 118.7(2) . . ? O38 N36 C34 117.3(3) . . ? O40 N39 O41 124.3(2) . . ? O40 N39 C32 118.4(2) . . ? O41 N39 C32 117.2(2) . . ? O43 C42 O44 125.3(3) . . ? O43 C42 C30 121.9(2) . . ? O44 C42 C30 112.8(2) . . ? C42 O44 H44 109(3) . . ? 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 O7 C1 C2 C3 -176.8(3) . . . . ? N6 C1 C2 C3 2.9(4) . . . . ? C1 C2 C3 C4 -31.7(5) . . . . ? C2 C3 C4 C5 53.7(5) . . . . ? C3 C4 C5 N6 -44.8(5) . . . . ? O7 C1 N6 C5 -175.4(2) . . . . ? C2 C1 N6 C5 4.9(4) . . . . ? C4 C5 N6 C1 15.5(4) . . . . ? O14 C8 C9 C10 171.6(3) . . . . ? N13 C8 C9 C10 -9.4(5) . . . . ? C8 C9 C10 C11 33.2(6) . . . . ? C9 C10 C11 C12 -49.5(6) . . . . ? C10 C11 C12 N13 40.4(6) . . . . ? O14 C8 N13 C12 -178.6(3) . . . . ? C9 C8 N13 C12 2.5(5) . . . . ? C11 C12 N13 C8 -17.2(5) . . . . ? C20 C15 C16 C17 -0.8(4) . . . . ? C27 C15 C16 C17 179.9(2) . . . . ? C15 C16 C17 C18 -0.6(4) . . . . ? C15 C16 C17 N24 178.8(2) . . . . ? C16 C17 C18 C19 1.4(4) . . . . ? N24 C17 C18 C19 -177.9(2) . . . . ? C17 C18 C19 C20 -1.0(4) . . . . ? C17 C18 C19 N21 179.6(2) . . . . ? C16 C15 C20 C19 1.2(4) . . . . ? C27 C15 C20 C19 -179.5(2) . . . . ? C18 C19 C20 C15 -0.3(4) . . . . ? N21 C19 C20 C15 179.2(2) . . . . ? C18 C19 N21 O22 -7.0(4) . . . . ? C20 C19 N21 O22 173.5(3) . . . . ? C18 C19 N21 O23 172.3(3) . . . . ? C20 C19 N21 O23 -7.2(4) . . . . ? C16 C17 N24 O25 176.8(3) . . . . ? C18 C17 N24 O25 -3.8(4) . . . . ? C16 C17 N24 O26 -3.8(4) . . . . ? C18 C17 N24 O26 175.6(2) . . . . ? C20 C15 C27 O28 171.8(3) . . . . ? C16 C15 C27 O28 -8.9(4) . . . . ? C20 C15 C27 O29 -8.4(4) . . . . ? C16 C15 C27 O29 170.9(2) . . . . ? C35 C30 C31 C32 -1.8(4) . . . . ? C42 C30 C31 C32 177.2(2) . . . . ? C30 C31 C32 C33 0.2(4) . . . . ? C30 C31 C32 N39 -179.6(2) . . . . ? C31 C32 C33 C34 1.2(4) . . . . ? N39 C32 C33 C34 -178.9(2) . . . . ? C32 C33 C34 C35 -1.2(4) . . . . ? C32 C33 C34 N36 179.7(2) . . . . ? C33 C34 C35 C30 -0.3(4) . . . . ? N36 C34 C35 C30 178.8(2) . . . . ? C31 C30 C35 C34 1.8(4) . . . . ? C42 C30 C35 C34 -177.2(2) . . . . ? C35 C34 N36 O37 166.6(3) . . . . ? C33 C34 N36 O37 -14.2(4) . . . . ? C35 C34 N36 O38 -15.4(4) . . . . ? C33 C34 N36 O38 163.8(3) . . . . ? C31 C32 N39 O40 168.9(2) . . . . ? C33 C32 N39 O40 -11.0(3) . . . . ? C31 C32 N39 O41 -10.9(3) . . . . ? C33 C32 N39 O41 169.3(2) . . . . ? C35 C30 C42 O43 -5.8(4) . . . . ? C31 C30 C42 O43 175.2(3) . . . . ? C35 C30 C42 O44 173.0(2) . . . . ? C31 C30 C42 O44 -5.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.952 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.060 # Attachment '6073_web_deposit_cif_file_5_AuroraJ.Cruz-Cabeza_1309426426.3i.cif' data_3i _database_code_depnum_ccdc_archive 'CCDC 832273' #TrackingRef '6073_web_deposit_cif_file_5_AuroraJ.Cruz-Cabeza_1309426426.3i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 O4, C4 H5 N O2' _chemical_formula_sum 'C11 H11 N O6' _chemical_formula_weight 253.21 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5358(2) _cell_length_b 7.6095(3) _cell_length_c 11.8452(4) _cell_angle_alpha 79.803(2) _cell_angle_beta 78.578(2) _cell_angle_gamma 75.337(2) _cell_volume 553.61(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5128 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 32.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.898 _exptl_absorpt_correction_T_max 1.009 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8631 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 32.05 _reflns_number_total 3823 _reflns_number_gt 2562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _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. ; _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^)+(0.0560P)^2^+0.2112P] 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_number_reflns 3823 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 C1 C 1.2302(2) 0.7396(2) 1.29002(13) 0.0280(3) Uani 1 1 d . . . H1A H 1.2312 0.8614 1.3083 0.034 Uiso 1 1 calc R . . H1B H 1.1714 0.6673 1.3615 0.034 Uiso 1 1 calc R . . C2 C 1.0988(2) 0.7589(2) 1.19282(13) 0.0277(3) Uani 1 1 d . . . H2A H 0.9728 0.7042 1.2215 0.033 Uiso 1 1 calc R . . H2B H 1.0488 0.8895 1.1623 0.033 Uiso 1 1 calc R . . C3 C 1.2496(2) 0.6575(2) 1.10060(12) 0.0240(3) Uani 1 1 d . . . N4 N 1.4468(2) 0.59831(18) 1.13395(10) 0.0259(3) Uani 1 1 d . . . H4 H 1.5597 0.5385 1.0910 0.031 Uiso 1 1 calc R . . C5 C 1.4520(2) 0.6414(2) 1.24140(13) 0.0256(3) Uani 1 1 d . . . O6 O 1.20957(17) 0.63049(16) 1.00912(9) 0.0300(3) Uani 1 1 d . . . O7 O 1.61480(18) 0.59960(18) 1.28460(10) 0.0350(3) Uani 1 1 d . . . C8 C 0.7575(2) 0.8029(2) 0.86464(13) 0.0249(3) Uani 1 1 d . . . C9 C 0.9119(2) 0.7156(2) 0.78017(13) 0.0255(3) Uani 1 1 d . . . H9A H 1.0546 0.6651 0.7943 0.031 Uiso 1 1 calc R . . C10 C 0.8549(2) 0.7035(2) 0.67620(13) 0.0250(3) Uani 1 1 d . . . H10A H 0.9599 0.6451 0.6185 0.030 Uiso 1 1 calc R . . C11 C 0.6447(2) 0.7759(2) 0.65424(12) 0.0236(3) Uani 1 1 d . . . C12 C 0.4930(2) 0.8668(2) 0.73953(13) 0.0247(3) Uani 1 1 d . . . C13 C 0.5497(2) 0.8805(2) 0.84449(13) 0.0263(3) Uani 1 1 d . . . H13A H 0.4471 0.9423 0.9016 0.032 Uiso 1 1 calc R . . O14 O 0.8042(2) 0.81705(17) 0.96913(10) 0.0338(3) Uani 1 1 d . . . H14 H 0.935(4) 0.752(3) 0.9727(18) 0.041 Uiso 1 1 d . . . O15 O 0.28885(18) 0.94221(18) 0.72343(11) 0.0365(3) Uani 1 1 d . . . H15 H 0.281(3) 0.916(3) 0.648(2) 0.044 Uiso 1 1 d . . . C16 C 0.5770(3) 0.7558(2) 0.54742(13) 0.0276(3) Uani 1 1 d . . . O17 O 0.39438(19) 0.81833(18) 0.52550(11) 0.0367(3) Uani 1 1 d . . . O18 O 0.7289(2) 0.66014(19) 0.47512(11) 0.0389(3) Uani 1 1 d . . . H18 H 0.673(4) 0.662(3) 0.414(2) 0.047 Uiso 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 C1 0.0277(7) 0.0304(7) 0.0252(7) -0.0098(6) -0.0016(5) -0.0034(6) C2 0.0239(7) 0.0293(7) 0.0287(7) -0.0092(6) -0.0043(5) -0.0004(6) C3 0.0229(7) 0.0260(7) 0.0228(6) -0.0026(5) -0.0050(5) -0.0046(5) N4 0.0202(6) 0.0363(7) 0.0213(6) -0.0100(5) -0.0047(4) -0.0013(5) C5 0.0261(7) 0.0296(7) 0.0223(7) -0.0060(5) -0.0045(5) -0.0061(6) O6 0.0262(5) 0.0405(6) 0.0235(5) -0.0078(4) -0.0078(4) -0.0023(5) O7 0.0280(6) 0.0502(7) 0.0285(6) -0.0137(5) -0.0099(4) -0.0020(5) C8 0.0269(7) 0.0254(7) 0.0243(7) -0.0044(5) -0.0083(5) -0.0054(6) C9 0.0213(7) 0.0293(7) 0.0263(7) -0.0039(5) -0.0079(5) -0.0031(6) C10 0.0223(7) 0.0276(7) 0.0245(7) -0.0057(5) -0.0044(5) -0.0023(6) C11 0.0239(7) 0.0242(7) 0.0235(7) -0.0040(5) -0.0074(5) -0.0037(5) C12 0.0205(7) 0.0236(7) 0.0303(7) -0.0055(5) -0.0072(5) -0.0019(5) C13 0.0239(7) 0.0276(7) 0.0277(7) -0.0086(6) -0.0044(5) -0.0029(6) O14 0.0311(6) 0.0429(7) 0.0288(6) -0.0135(5) -0.0121(4) 0.0005(5) O15 0.0231(6) 0.0455(7) 0.0412(7) -0.0165(6) -0.0122(5) 0.0046(5) C16 0.0298(8) 0.0289(7) 0.0257(7) -0.0034(6) -0.0089(6) -0.0060(6) O17 0.0318(6) 0.0444(7) 0.0356(6) -0.0093(5) -0.0157(5) -0.0007(5) O18 0.0335(6) 0.0552(8) 0.0276(6) -0.0167(5) -0.0102(5) 0.0027(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 C1 C5 1.505(2) . ? C1 C2 1.534(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.499(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O6 1.2262(18) . ? C3 N4 1.3654(18) . ? N4 C5 1.3781(18) . ? N4 H4 0.8800 . ? C5 O7 1.2175(18) . ? C8 O14 1.3602(17) . ? C8 C13 1.387(2) . ? C8 C9 1.399(2) . ? C9 C10 1.379(2) . ? C9 H9A 0.9500 . ? C10 C11 1.402(2) . ? C10 H10A 0.9500 . ? C11 C12 1.409(2) . ? C11 C16 1.465(2) . ? C12 O15 1.3489(18) . ? C12 C13 1.393(2) . ? C13 H13A 0.9500 . ? O14 H14 0.88(2) . ? O15 H15 0.97(2) . ? C16 O17 1.2290(19) . ? C16 O18 1.329(2) . ? O18 H18 0.87(2) . ? 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 C5 C1 C2 104.29(12) . . ? C5 C1 H1A 110.9 . . ? C2 C1 H1A 110.9 . . ? C5 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? H1A C1 H1B 108.9 . . ? C3 C2 C1 104.94(12) . . ? C3 C2 H2A 110.8 . . ? C1 C2 H2A 110.8 . . ? C3 C2 H2B 110.8 . . ? C1 C2 H2B 110.8 . . ? H2A C2 H2B 108.8 . . ? O6 C3 N4 123.96(13) . . ? O6 C3 C2 127.42(13) . . ? N4 C3 C2 108.62(12) . . ? C3 N4 C5 113.51(12) . . ? C3 N4 H4 123.2 . . ? C5 N4 H4 123.2 . . ? O7 C5 N4 122.36(14) . . ? O7 C5 C1 129.19(14) . . ? N4 C5 C1 108.44(12) . . ? O14 C8 C13 117.13(13) . . ? O14 C8 C9 121.84(13) . . ? C13 C8 C9 121.03(13) . . ? C10 C9 C8 119.34(13) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? C9 C10 C11 121.12(13) . . ? C9 C10 H10A 119.4 . . ? C11 C10 H10A 119.4 . . ? C10 C11 C12 118.58(13) . . ? C10 C11 C16 122.21(13) . . ? C12 C11 C16 119.19(13) . . ? O15 C12 C13 117.67(13) . . ? O15 C12 C11 121.72(13) . . ? C13 C12 C11 120.60(13) . . ? C8 C13 C12 119.30(14) . . ? C8 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C8 O14 H14 107.0(14) . . ? C12 O15 H15 105.2(13) . . ? O17 C16 O18 121.64(14) . . ? O17 C16 C11 123.71(14) . . ? O18 C16 C11 114.64(13) . . ? C16 O18 H18 106.5(15) . . ? 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 C1 C2 C3 4.48(16) . . . . ? C1 C2 C3 O6 176.55(15) . . . . ? C1 C2 C3 N4 -4.02(17) . . . . ? O6 C3 N4 C5 -178.66(15) . . . . ? C2 C3 N4 C5 1.89(18) . . . . ? C3 N4 C5 O7 -179.81(15) . . . . ? C3 N4 C5 C1 1.17(18) . . . . ? C2 C1 C5 O7 177.49(17) . . . . ? C2 C1 C5 N4 -3.58(17) . . . . ? O14 C8 C9 C10 179.31(14) . . . . ? C13 C8 C9 C10 -1.3(2) . . . . ? C8 C9 C10 C11 -0.5(2) . . . . ? C9 C10 C11 C12 1.9(2) . . . . ? C9 C10 C11 C16 -176.41(14) . . . . ? C10 C11 C12 O15 178.97(14) . . . . ? C16 C11 C12 O15 -2.7(2) . . . . ? C10 C11 C12 C13 -1.5(2) . . . . ? C16 C11 C12 C13 176.86(14) . . . . ? O14 C8 C13 C12 -178.90(14) . . . . ? C9 C8 C13 C12 1.7(2) . . . . ? O15 C12 C13 C8 179.31(14) . . . . ? C11 C12 C13 C8 -0.3(2) . . . . ? C10 C11 C16 O17 -179.68(15) . . . . ? C12 C11 C16 O17 2.0(2) . . . . ? C10 C11 C16 O18 1.5(2) . . . . ? C12 C11 C16 O18 -176.75(14) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 32.05 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.382 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.059