# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yu-Bin Dong' _publ_contact_author_email YUBINDONG@SDNU.EDU.CN _publ_section_title ; Co-crystallization of oxadiazole-bridged pyridyl-N-oxide building modules with R-aromatics (R = -OH, -NH2 and -COOH) ; loop_ _publ_author_name 'Yu-Bin Dong' 'Gui-Ge Hou' 'Ru-Qi Huang' 'Jian-Ping Ma' 'Le Wang' ; Ping Wang ; # Attachment '1.cif' #========================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 735624' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H14 N4 O5' _chemical_formula_sum 'C18 H14 N4 O5' _chemical_formula_weight 366.33 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 9.991(2) _cell_length_b 22.751(5) _cell_length_c 7.1579(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1627.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2018 _cell_measurement_theta_min 3.363 _cell_measurement_theta_max 23.161 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7819 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1520 _reflns_number_gt 1165 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0589P)^2^+0.4063P] 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_number_reflns 1520 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.09953(17) 0.16878(7) 0.8022(2) 0.0416(4) Uani 1 1 d . . . C2 C 0.22625(17) 0.14550(7) 0.8673(2) 0.0437(4) Uani 1 1 d . . . C3 C 0.32418(19) 0.18287(8) 0.9340(3) 0.0537(5) Uani 1 1 d . . . H3 H 0.3087 0.2232 0.9373 0.064 Uiso 1 1 calc R . . C4 C 0.4435(2) 0.16092(8) 0.9952(3) 0.0570(6) Uani 1 1 d . . . H4 H 0.5088 0.1865 1.0397 0.068 Uiso 1 1 calc R . . C5 C 0.3745(2) 0.06591(8) 0.9285(4) 0.0682(7) Uani 1 1 d . . . H5 H 0.3914 0.0257 0.9274 0.082 Uiso 1 1 calc R . . C6 C 0.2546(2) 0.08647(8) 0.8654(3) 0.0628(6) Uani 1 1 d . . . H6 H 0.1910 0.0601 0.8205 0.075 Uiso 1 1 calc R . . C7 C 0.0000 0.15638(11) 0.2500 0.0484(6) Uani 1 2 d S . . H7 H 0.0000 0.1973 0.2500 0.058 Uiso 1 2 calc SR . . C8 C 0.10847(18) 0.12635(8) 0.3198(3) 0.0474(5) Uani 1 1 d . . . C9 C 0.1090(2) 0.06633(9) 0.3213(4) 0.0709(7) Uani 1 1 d . . . H9 H 0.1816 0.0457 0.3695 0.085 Uiso 1 1 calc R . . C10 C 0.0000 0.03702(13) 0.2500 0.0924(13) Uani 1 2 d S . . H10 H 0.0000 -0.0039 0.2500 0.111 Uiso 1 2 calc SR . . N1 N 0.06523(16) 0.22301(6) 0.7848(2) 0.0521(4) Uani 1 1 d . . . N2 N 0.46808(15) 0.10281(7) 0.9918(2) 0.0537(5) Uani 1 1 d . . . O1 O 0.0000 0.13146(6) 0.7500 0.0443(5) Uani 1 2 d S . . O2 O 0.58373(14) 0.08247(6) 1.0492(2) 0.0716(5) Uani 1 1 d . . . O3 O 0.21242(14) 0.15791(6) 0.3891(2) 0.0669(5) Uani 1 1 d . . . H3A H 0.2763 0.1360 0.4076 0.100 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 C1 0.0403(10) 0.0348(9) 0.0498(11) -0.0018(7) 0.0003(8) -0.0045(7) C2 0.0409(10) 0.0392(9) 0.0510(11) -0.0005(8) -0.0001(8) -0.0023(8) C3 0.0473(11) 0.0406(10) 0.0734(13) -0.0103(9) -0.0039(10) -0.0014(8) C4 0.0451(11) 0.0489(12) 0.0771(15) -0.0128(10) -0.0075(10) -0.0060(8) C5 0.0533(13) 0.0384(10) 0.1128(19) -0.0017(11) -0.0228(13) -0.0010(9) C6 0.0484(11) 0.0385(11) 0.1014(17) -0.0013(10) -0.0227(11) -0.0043(9) C7 0.0488(15) 0.0401(13) 0.0562(16) 0.000 0.0030(13) 0.000 C8 0.0402(10) 0.0486(11) 0.0535(11) -0.0023(8) 0.0000(9) -0.0042(8) C9 0.0545(13) 0.0477(12) 0.110(2) 0.0039(12) -0.0263(13) 0.0033(9) C10 0.069(2) 0.0406(16) 0.168(4) 0.000 -0.045(2) 0.000 N1 0.0442(9) 0.0377(8) 0.0743(11) -0.0012(7) -0.0044(8) -0.0008(7) N2 0.0411(9) 0.0496(9) 0.0703(11) -0.0011(8) -0.0095(8) 0.0020(7) O1 0.0406(10) 0.0335(9) 0.0588(11) 0.000 -0.0070(8) 0.000 O2 0.0440(8) 0.0637(9) 0.1070(13) -0.0019(8) -0.0217(8) 0.0069(7) O3 0.0505(9) 0.0574(9) 0.0929(12) -0.0058(8) -0.0139(8) -0.0077(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.287(2) . ? C1 O1 1.3597(19) . ? C1 C2 1.449(2) . ? C2 C6 1.373(3) . ? C2 C3 1.381(2) . ? C3 C4 1.365(3) . ? C3 H3 0.9300 . ? C4 N2 1.345(3) . ? C4 H4 0.9300 . ? C5 N2 1.336(2) . ? C5 C6 1.363(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.375(2) 4 ? C7 C8 1.375(2) . ? C7 H7 0.9300 . ? C8 O3 1.356(2) . ? C8 C9 1.366(3) . ? C9 C10 1.375(2) . ? C9 H9 0.9300 . ? C10 C9 1.375(2) 4 ? C10 H10 0.9300 . ? N1 N1 1.395(3) 4_556 ? N2 O2 1.311(2) . ? O1 C1 1.3597(19) 4_556 ? O3 H3A 0.8200 . ? 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 N1 C1 O1 112.17(15) . . ? N1 C1 C2 127.89(15) . . ? O1 C1 C2 119.94(14) . . ? C6 C2 C3 117.36(17) . . ? C6 C2 C1 122.30(16) . . ? C3 C2 C1 120.34(16) . . ? C4 C3 C2 120.30(17) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? N2 C4 C3 120.89(17) . . ? N2 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? N2 C5 C6 120.80(18) . . ? N2 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C2 120.90(18) . . ? C5 C6 H6 119.5 . . ? C2 C6 H6 119.5 . . ? C8 C7 C8 120.4(2) 4 . ? C8 C7 H7 119.8 4 . ? C8 C7 H7 119.8 . . ? O3 C8 C9 121.56(17) . . ? O3 C8 C7 118.23(17) . . ? C9 C8 C7 120.19(18) . . ? C8 C9 C10 118.6(2) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C9 C10 C9 122.0(3) . 4 ? C9 C10 H10 119.0 . . ? C9 C10 H10 119.0 4 . ? C1 N1 N1 106.46(10) . 4_556 ? O2 N2 C5 120.09(16) . . ? O2 N2 C4 120.16(16) . . ? C5 N2 C4 119.75(17) . . ? C1 O1 C1 102.74(17) . 4_556 ? C8 O3 H3A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C6 -174.6(2) . . . . ? O1 C1 C2 C6 5.1(3) . . . . ? N1 C1 C2 C3 5.2(3) . . . . ? O1 C1 C2 C3 -175.04(16) . . . . ? C6 C2 C3 C4 -0.1(3) . . . . ? C1 C2 C3 C4 -179.96(18) . . . . ? C2 C3 C4 N2 0.0(3) . . . . ? N2 C5 C6 C2 -0.7(4) . . . . ? C3 C2 C6 C5 0.5(3) . . . . ? C1 C2 C6 C5 -179.7(2) . . . . ? C8 C7 C8 O3 -179.3(2) 4 . . . ? C8 C7 C8 C9 -0.35(16) 4 . . . ? O3 C8 C9 C10 179.59(17) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 C9 -0.34(16) . . . 4 ? O1 C1 N1 N1 -0.5(2) . . . 4_556 ? C2 C1 N1 N1 179.29(19) . . . 4_556 ? C6 C5 N2 O2 -178.9(2) . . . . ? C6 C5 N2 C4 0.6(4) . . . . ? C3 C4 N2 O2 179.26(19) . . . . ? C3 C4 N2 C5 -0.2(3) . . . . ? N1 C1 O1 C1 0.19(10) . . . 4_556 ? C2 C1 O1 C1 -179.6(2) . . . 4_556 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.82 1.88 2.700(2) 176.9 4_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.154 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.038 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 735625' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 N4 O6' _chemical_formula_sum 'C19 H14 N4 O6' _chemical_formula_weight 394.34 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 30.724(15) _cell_length_b 7.369(4) _cell_length_c 20.920(10) _cell_angle_alpha 90.00 _cell_angle_beta 131.282(6) _cell_angle_gamma 90.00 _cell_volume 3559(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1381 _cell_measurement_theta_min 2.591 _cell_measurement_theta_max 20.775 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8948 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4482 _reflns_number_gt 3260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(15) _refine_ls_number_reflns 4482 _refine_ls_number_parameters 527 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0873 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.2342(2) 0.4214(8) 0.2608(3) 0.0555(16) Uani 1 1 d . . . H1 H 0.2114 0.4347 0.2024 0.067 Uiso 1 1 calc R . . C2 C 0.2094(2) 0.3623(8) 0.2922(3) 0.0587(16) Uani 1 1 d . . . H2 H 0.1700 0.3355 0.2553 0.070 Uiso 1 1 calc R . . C3 C 0.2431(2) 0.3423(7) 0.3797(3) 0.0396(12) Uani 1 1 d . . . C4 C 0.3006(2) 0.3851(7) 0.4307(3) 0.0509(14) Uani 1 1 d . . . H4 H 0.3244 0.3726 0.4893 0.061 Uiso 1 1 calc R . . C5 C 0.3236(2) 0.4452(8) 0.3974(3) 0.0549(15) Uani 1 1 d . . . H5 H 0.3626 0.4764 0.4334 0.066 Uiso 1 1 calc R . . C6 C 0.2171(2) 0.2742(7) 0.4139(3) 0.0427(13) Uani 1 1 d . . . C7 C 0.2135(2) 0.1806(7) 0.5047(3) 0.0432(12) Uani 1 1 d . . . C8 C 0.2349(2) 0.1284(7) 0.5891(3) 0.0420(12) Uani 1 1 d . . . C9 C 0.1966(2) 0.0765(8) 0.5987(3) 0.0543(15) Uani 1 1 d . . . H9 H 0.1571 0.0763 0.5519 0.065 Uiso 1 1 calc R . . C10 C 0.2163(3) 0.0246(8) 0.6774(4) 0.0628(16) Uani 1 1 d . . . H10 H 0.1900 -0.0116 0.6830 0.075 Uiso 1 1 calc R . . C11 C 0.3118(2) 0.0780(7) 0.7375(3) 0.0579(15) Uani 1 1 d . . . H11 H 0.3513 0.0802 0.7847 0.069 Uiso 1 1 calc R . . C12 C 0.2925(2) 0.1269(7) 0.6596(3) 0.0528(14) Uani 1 1 d . . . H12 H 0.3193 0.1600 0.6544 0.063 Uiso 1 1 calc R . . C13 C 0.2336(2) 0.6273(8) 0.5769(3) 0.0543(14) Uani 1 1 d . . . C14 C 0.2246(2) 0.6929(7) 0.5020(3) 0.0513(13) Uani 1 1 d . . . C15 C 0.1688(2) 0.6816(8) 0.4231(4) 0.0672(17) Uani 1 1 d . . . H15 H 0.1387 0.6354 0.4184 0.081 Uiso 1 1 calc R . . C16 C 0.1589(3) 0.7401(9) 0.3518(3) 0.079(2) Uani 1 1 d . . . H16 H 0.1218 0.7306 0.2989 0.095 Uiso 1 1 calc R . . C17 C 0.2028(3) 0.8130(8) 0.3568(3) 0.0678(17) Uani 1 1 d . . . H17 H 0.1954 0.8522 0.3082 0.081 Uiso 1 1 calc R . . C18 C 0.2567(2) 0.8253(7) 0.4345(3) 0.0550(14) Uani 1 1 d . . . C19 C 0.2684(2) 0.7639(7) 0.5080(3) 0.0519(14) Uani 1 1 d . . . H19 H 0.3057 0.7715 0.5606 0.062 Uiso 1 1 calc R . . C20 C 0.4154(2) 0.4314(7) 0.2237(3) 0.0535(14) Uani 1 1 d . . . H20 H 0.3755 0.4365 0.1793 0.064 Uiso 1 1 calc R . . C21 C 0.4377(2) 0.3852(7) 0.3041(3) 0.0486(13) Uani 1 1 d . . . H21 H 0.4128 0.3589 0.3137 0.058 Uiso 1 1 calc R . . C22 C 0.4965(2) 0.3779(7) 0.3700(3) 0.0402(12) Uani 1 1 d . . . C23 C 0.5323(2) 0.4160(7) 0.3534(3) 0.0489(14) Uani 1 1 d . . . H23 H 0.5723 0.4129 0.3968 0.059 Uiso 1 1 calc R . . C24 C 0.5075(2) 0.4584(8) 0.2720(3) 0.0573(16) Uani 1 1 d . . . H24 H 0.5314 0.4809 0.2603 0.069 Uiso 1 1 calc R . . C25 C 0.5214(2) 0.3369(7) 0.4558(3) 0.0420(12) Uani 1 1 d . . . C26 C 0.5241(2) 0.2511(7) 0.5556(3) 0.0437(13) Uani 1 1 d . . . C27 C 0.5024(2) 0.1802(7) 0.5958(3) 0.0401(12) Uani 1 1 d . . . C28 C 0.5386(2) 0.1779(8) 0.6829(3) 0.0498(14) Uani 1 1 d . . . H28 H 0.5760 0.2237 0.7155 0.060 Uiso 1 1 calc R . . C29 C 0.5203(2) 0.1095(8) 0.7216(3) 0.0602(16) Uani 1 1 d . . . H29 H 0.5456 0.1073 0.7806 0.072 Uiso 1 1 calc R . . C30 C 0.4299(2) 0.0431(8) 0.5905(3) 0.0536(14) Uani 1 1 d . . . H30 H 0.3927 -0.0031 0.5593 0.064 Uiso 1 1 calc R . . C31 C 0.4472(2) 0.1094(7) 0.5486(3) 0.0480(13) Uani 1 1 d . . . H31 H 0.4221 0.1065 0.4895 0.058 Uiso 1 1 calc R . . C32 C 0.4809(2) 0.1663(7) 0.8935(3) 0.0512(14) Uani 1 1 d . . . C33 C 0.5343(3) 0.1059(7) 0.9302(4) 0.0584(15) Uani 1 1 d . . . H33 H 0.5417 0.0586 0.8969 0.070 Uiso 1 1 calc R . . C34 C 0.5786(3) 0.1149(8) 1.0188(4) 0.0708(18) Uani 1 1 d . . . H34 H 0.6155 0.0727 1.0446 0.085 Uiso 1 1 calc R . . C35 C 0.5676(2) 0.1859(8) 1.0674(4) 0.0622(16) Uani 1 1 d . . . H35 H 0.5972 0.1919 1.1261 0.075 Uiso 1 1 calc R . . C36 C 0.5127(2) 0.2490(7) 1.0297(3) 0.0463(12) Uani 1 1 d . . . C37 C 0.4693(2) 0.2411(7) 0.9427(3) 0.0497(14) Uani 1 1 d . . . H37 H 0.4326 0.2850 0.9166 0.060 Uiso 1 1 calc R . . C38 C 0.5024(2) 0.3202(7) 1.0850(3) 0.0530(14) Uani 1 1 d . . . N1 N 0.16366(18) 0.2354(6) 0.3729(2) 0.0533(12) Uani 1 1 d . . . N2 N 0.16146(18) 0.1748(6) 0.4341(3) 0.0547(12) Uani 1 1 d . . . N3 N 0.2736(2) 0.0261(6) 0.7462(3) 0.0553(12) Uani 1 1 d . . . N4 N 0.2905(2) 0.4603(6) 0.3128(3) 0.0559(12) Uani 1 1 d . . . N5 N 0.57457(17) 0.3567(6) 0.5260(3) 0.0498(11) Uani 1 1 d . . . N6 N 0.57625(17) 0.3002(6) 0.5921(2) 0.0508(11) Uani 1 1 d . . . N7 N 0.4662(2) 0.0444(6) 0.6760(3) 0.0539(12) Uani 1 1 d . . . N8 N 0.45029(19) 0.4688(6) 0.2088(3) 0.0484(11) Uani 1 1 d . . . O1 O 0.25185(13) 0.2424(5) 0.49885(19) 0.0420(8) Uani 1 1 d . . . O2 O 0.29248(19) -0.0254(6) 0.8205(2) 0.0814(14) Uani 1 1 d . . . O3 O 0.31435(17) 0.5129(6) 0.2813(2) 0.0768(13) Uani 1 1 d . . . O4 O 0.48639(14) 0.2716(5) 0.46974(18) 0.0433(9) Uani 1 1 d . . . O5 O 0.44938(19) -0.0251(6) 0.7141(2) 0.0780(13) Uani 1 1 d . . . O6 O 0.42768(16) 0.5197(6) 0.1314(2) 0.0675(12) Uani 1 1 d . . . O7 O 0.45012(15) 0.3858(6) 1.0428(2) 0.0621(11) Uani 1 1 d . . . H7 H 0.4471 0.4251 1.0764 0.093 Uiso 1 1 calc R . . O8 O 0.53808(18) 0.3180(6) 1.1611(2) 0.0927(15) Uani 1 1 d . . . O9 O 0.43655(16) 0.1588(6) 0.8079(2) 0.0722(12) Uani 1 1 d . . . H9A H 0.4470 0.1034 0.7861 0.108 Uiso 1 1 calc R . . O10 O 0.19606(16) 0.5679(6) 0.5742(2) 0.0845(13) Uani 1 1 d . . . O11 O 0.28874(15) 0.6354(6) 0.6495(2) 0.0704(12) Uani 1 1 d . . . H11A H 0.2912 0.5986 0.6888 0.106 Uiso 1 1 calc R . . O12 O 0.30204(17) 0.8899(7) 0.4442(2) 0.0802(13) Uani 1 1 d . . . H12A H 0.2912 0.9162 0.3975 0.120 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 C1 0.058(4) 0.079(5) 0.038(3) 0.005(3) 0.035(3) 0.005(3) C2 0.043(3) 0.077(4) 0.039(3) 0.002(3) 0.020(3) 0.008(3) C3 0.037(3) 0.043(3) 0.033(3) -0.005(2) 0.021(3) 0.002(2) C4 0.055(3) 0.054(4) 0.032(3) -0.010(2) 0.024(3) -0.009(3) C5 0.055(3) 0.069(4) 0.031(3) -0.012(2) 0.024(3) -0.020(3) C6 0.040(3) 0.046(3) 0.037(3) 0.000(2) 0.023(3) 0.003(2) C7 0.039(3) 0.049(3) 0.043(3) -0.006(2) 0.028(3) -0.004(2) C8 0.050(3) 0.035(3) 0.043(3) -0.007(2) 0.032(3) -0.009(2) C9 0.051(3) 0.064(4) 0.057(3) 0.001(3) 0.039(3) 0.000(3) C10 0.066(4) 0.071(5) 0.077(4) -0.007(3) 0.058(4) -0.013(3) C11 0.052(3) 0.065(4) 0.043(3) -0.008(3) 0.026(3) -0.013(3) C12 0.059(4) 0.060(4) 0.045(3) -0.008(3) 0.037(3) -0.015(3) C13 0.056(4) 0.047(4) 0.064(4) -0.008(3) 0.041(3) 0.000(3) C14 0.048(3) 0.044(3) 0.052(3) -0.006(2) 0.029(3) 0.008(2) C15 0.041(3) 0.060(4) 0.071(4) -0.009(3) 0.025(3) 0.003(3) C16 0.060(4) 0.079(5) 0.043(4) 0.000(3) 0.010(3) 0.010(4) C17 0.073(4) 0.055(4) 0.050(4) -0.002(3) 0.030(4) 0.001(3) C18 0.057(4) 0.050(3) 0.054(3) -0.012(3) 0.034(3) -0.009(3) C19 0.048(3) 0.053(4) 0.043(3) -0.006(3) 0.025(3) -0.002(3) C20 0.046(3) 0.072(4) 0.048(3) -0.005(3) 0.033(3) -0.002(3) C21 0.043(3) 0.067(4) 0.050(3) -0.010(3) 0.037(3) -0.012(3) C22 0.048(3) 0.039(3) 0.044(3) -0.002(2) 0.035(3) 0.001(2) C23 0.049(3) 0.063(4) 0.044(3) -0.002(2) 0.034(3) -0.001(3) C24 0.058(4) 0.071(4) 0.065(4) 0.010(3) 0.050(4) 0.003(3) C25 0.045(3) 0.042(3) 0.052(3) -0.005(2) 0.038(3) -0.004(2) C26 0.042(3) 0.053(4) 0.035(3) -0.003(2) 0.024(3) 0.001(2) C27 0.047(3) 0.037(3) 0.042(3) 0.003(2) 0.031(3) 0.003(2) C28 0.045(3) 0.070(4) 0.037(3) -0.001(2) 0.028(3) -0.003(3) C29 0.062(4) 0.076(4) 0.035(3) -0.001(3) 0.028(3) -0.001(3) C30 0.058(3) 0.063(4) 0.047(3) -0.014(3) 0.038(3) -0.011(3) C31 0.051(3) 0.055(4) 0.042(3) 0.002(2) 0.032(3) 0.003(3) C32 0.053(4) 0.047(4) 0.061(4) 0.007(3) 0.040(3) 0.003(3) C33 0.066(4) 0.048(4) 0.080(4) 0.007(3) 0.056(4) 0.005(3) C34 0.059(4) 0.067(4) 0.104(5) 0.023(4) 0.062(4) 0.018(3) C35 0.038(3) 0.075(4) 0.062(4) 0.018(3) 0.028(3) 0.012(3) C36 0.044(3) 0.046(3) 0.049(3) 0.007(2) 0.031(3) -0.001(2) C37 0.039(3) 0.058(4) 0.054(3) 0.005(2) 0.032(3) 0.005(2) C38 0.059(4) 0.050(4) 0.048(3) 0.017(3) 0.034(3) 0.012(3) N1 0.044(3) 0.073(3) 0.040(2) 0.001(2) 0.026(2) -0.004(2) N2 0.045(3) 0.071(3) 0.044(3) -0.002(2) 0.027(2) -0.007(2) N3 0.083(4) 0.049(3) 0.055(3) -0.007(2) 0.055(3) -0.008(3) N4 0.060(3) 0.056(3) 0.060(3) -0.010(2) 0.043(3) -0.015(2) N5 0.045(3) 0.064(3) 0.048(3) -0.004(2) 0.034(2) -0.005(2) N6 0.041(3) 0.063(3) 0.045(2) -0.002(2) 0.027(2) -0.002(2) N7 0.076(3) 0.053(3) 0.056(3) -0.003(2) 0.053(3) -0.004(3) N8 0.052(3) 0.057(3) 0.046(3) 0.000(2) 0.036(2) 0.006(2) O1 0.0372(19) 0.054(2) 0.0358(18) 0.0009(15) 0.0244(16) -0.0017(16) O2 0.131(4) 0.080(3) 0.057(2) 0.000(2) 0.072(3) -0.002(3) O3 0.085(3) 0.102(3) 0.067(2) -0.014(2) 0.060(3) -0.036(2) O4 0.044(2) 0.054(3) 0.0375(19) -0.0046(15) 0.0297(17) -0.0029(16) O5 0.126(4) 0.074(3) 0.090(3) -0.011(2) 0.095(3) -0.024(3) O6 0.074(3) 0.089(3) 0.050(2) 0.021(2) 0.046(2) 0.022(2) O7 0.053(2) 0.084(3) 0.048(2) 0.0096(19) 0.033(2) 0.024(2) O8 0.068(3) 0.141(4) 0.043(2) 0.009(2) 0.026(2) 0.032(3) O9 0.068(3) 0.099(4) 0.055(2) -0.017(2) 0.043(2) -0.003(2) O10 0.058(3) 0.129(4) 0.076(3) -0.012(2) 0.048(2) -0.027(2) O11 0.051(2) 0.106(4) 0.056(2) 0.011(2) 0.036(2) 0.002(2) O12 0.078(3) 0.109(4) 0.051(2) 0.003(2) 0.042(2) -0.025(3) _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 N4 1.334(6) . ? C1 C2 1.365(7) . ? C1 H1 0.9300 . ? C2 C3 1.393(6) . ? C2 H2 0.9300 . ? C3 C4 1.370(7) . ? C3 C6 1.467(6) . ? C4 C5 1.350(7) . ? C4 H4 0.9300 . ? C5 N4 1.344(6) . ? C5 H5 0.9300 . ? C6 N1 1.287(6) . ? C6 O1 1.360(5) . ? C7 N2 1.273(6) . ? C7 O1 1.343(6) . ? C7 C8 1.471(6) . ? C8 C12 1.364(7) . ? C8 C9 1.373(7) . ? C9 C10 1.381(7) . ? C9 H9 0.9300 . ? C10 N3 1.352(7) . ? C10 H10 0.9300 . ? C11 N3 1.357(6) . ? C11 C12 1.365(7) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O10 1.198(6) . ? C13 O11 1.337(6) . ? C13 C14 1.481(7) . ? C14 C19 1.369(7) . ? C14 C15 1.392(7) . ? C15 C16 1.380(8) . ? C15 H15 0.9300 . ? C16 C17 1.390(8) . ? C16 H16 0.9300 . ? C17 C18 1.357(7) . ? C17 H17 0.9300 . ? C18 O12 1.353(6) . ? C18 C19 1.405(7) . ? C19 H19 0.9300 . ? C20 N8 1.327(6) . ? C20 C21 1.376(7) . ? C20 H20 0.9300 . ? C21 C22 1.372(6) . ? C21 H21 0.9300 . ? C22 C23 1.382(6) . ? C22 C25 1.445(6) . ? C23 C24 1.367(7) . ? C23 H23 0.9300 . ? C24 N8 1.334(6) . ? C24 H24 0.9300 . ? C25 N5 1.297(6) . ? C25 O4 1.372(5) . ? C26 N6 1.291(6) . ? C26 O4 1.358(5) . ? C26 C27 1.470(6) . ? C27 C28 1.372(6) . ? C27 C31 1.385(7) . ? C28 C29 1.349(7) . ? C28 H28 0.9300 . ? C29 N7 1.348(7) . ? C29 H29 0.9300 . ? C30 N7 1.345(6) . ? C30 C31 1.380(7) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C33 1.349(7) . ? C32 O9 1.359(5) . ? C32 C37 1.405(7) . ? C33 C34 1.402(8) . ? C33 H33 0.9300 . ? C34 C35 1.368(8) . ? C34 H34 0.9300 . ? C35 C36 1.389(7) . ? C35 H35 0.9300 . ? C36 C37 1.375(6) . ? C36 C38 1.482(7) . ? C37 H37 0.9300 . ? C38 O8 1.197(6) . ? C38 O7 1.312(6) . ? N1 N2 1.401(5) . ? N3 O2 1.307(5) . ? N4 O3 1.325(5) . ? N5 N6 1.413(5) . ? N7 O5 1.306(5) . ? N8 O6 1.327(5) . ? O7 H7 0.8200 . ? O9 H9A 0.8200 . ? O11 H11A 0.8200 . ? O12 H12A 0.8200 . ? 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 N4 C1 C2 120.9(5) . . ? N4 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.9(5) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 117.2(5) . . ? C4 C3 C6 122.5(4) . . ? C2 C3 C6 120.3(4) . . ? C5 C4 C3 121.3(4) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? N4 C5 C4 120.6(5) . . ? N4 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N1 C6 O1 112.9(4) . . ? N1 C6 C3 128.0(4) . . ? O1 C6 C3 119.1(4) . . ? N2 C7 O1 114.3(4) . . ? N2 C7 C8 127.5(5) . . ? O1 C7 C8 118.2(4) . . ? C12 C8 C9 117.7(5) . . ? C12 C8 C7 122.3(5) . . ? C9 C8 C7 120.0(5) . . ? C8 C9 C10 120.5(5) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? N3 C10 C9 120.4(5) . . ? N3 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? N3 C11 C12 120.1(5) . . ? N3 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C8 C12 C11 121.7(5) . . ? C8 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? O10 C13 O11 121.9(5) . . ? O10 C13 C14 124.6(5) . . ? O11 C13 C14 113.5(5) . . ? C19 C14 C15 119.8(5) . . ? C19 C14 C13 122.8(5) . . ? C15 C14 C13 117.3(5) . . ? C16 C15 C14 119.0(6) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 121.9(6) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 118.2(6) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? O12 C18 C17 121.7(5) . . ? O12 C18 C19 117.1(5) . . ? C17 C18 C19 121.2(6) . . ? C14 C19 C18 119.9(5) . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? N8 C20 C21 120.7(5) . . ? N8 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 120.1(5) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 118.5(4) . . ? C21 C22 C25 121.5(4) . . ? C23 C22 C25 119.9(4) . . ? C24 C23 C22 118.6(5) . . ? C24 C23 H23 120.7 . . ? C22 C23 H23 120.7 . . ? N8 C24 C23 122.2(5) . . ? N8 C24 H24 118.9 . . ? C23 C24 H24 118.9 . . ? N5 C25 O4 112.2(4) . . ? N5 C25 C22 128.3(4) . . ? O4 C25 C22 119.4(4) . . ? N6 C26 O4 113.2(4) . . ? N6 C26 C27 127.9(4) . . ? O4 C26 C27 118.9(4) . . ? C28 C27 C31 118.6(4) . . ? C28 C27 C26 119.3(4) . . ? C31 C27 C26 122.1(4) . . ? C29 C28 C27 120.5(5) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? N7 C29 C28 121.1(5) . . ? N7 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? N7 C30 C31 120.9(5) . . ? N7 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C30 C31 C27 119.0(5) . . ? C30 C31 H31 120.5 . . ? C27 C31 H31 120.5 . . ? C33 C32 O9 121.4(5) . . ? C33 C32 C37 121.0(5) . . ? O9 C32 C37 117.6(4) . . ? C32 C33 C34 119.4(5) . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C35 C34 C33 120.0(5) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C36 120.6(5) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C37 C36 C35 119.4(5) . . ? C37 C36 C38 121.9(4) . . ? C35 C36 C38 118.7(5) . . ? C36 C37 C32 119.5(5) . . ? C36 C37 H37 120.2 . . ? C32 C37 H37 120.2 . . ? O8 C38 O7 122.7(5) . . ? O8 C38 C36 123.6(5) . . ? O7 C38 C36 113.7(4) . . ? C6 N1 N2 105.7(4) . . ? C7 N2 N1 105.6(4) . . ? O2 N3 C10 120.6(5) . . ? O2 N3 C11 119.9(5) . . ? C10 N3 C11 119.5(4) . . ? O3 N4 C1 120.2(4) . . ? O3 N4 C5 119.6(5) . . ? C1 N4 C5 120.1(5) . . ? C25 N5 N6 106.2(4) . . ? C26 N6 N5 105.9(4) . . ? O5 N7 C30 119.6(5) . . ? O5 N7 C29 120.6(5) . . ? C30 N7 C29 119.7(5) . . ? C20 N8 O6 119.4(4) . . ? C20 N8 C24 119.8(4) . . ? O6 N8 C24 120.8(4) . . ? C7 O1 C6 101.4(4) . . ? C26 O4 C25 102.4(4) . . ? C38 O7 H7 109.5 . . ? C32 O9 H9A 109.5 . . ? C13 O11 H11A 109.5 . . ? C18 O12 H12A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 C3 0.1(8) . . . . ? C1 C2 C3 C4 0.4(8) . . . . ? C1 C2 C3 C6 -178.3(5) . . . . ? C2 C3 C4 C5 0.4(8) . . . . ? C6 C3 C4 C5 179.1(5) . . . . ? C3 C4 C5 N4 -1.7(8) . . . . ? C4 C3 C6 N1 177.5(5) . . . . ? C2 C3 C6 N1 -3.9(8) . . . . ? C4 C3 C6 O1 -3.8(7) . . . . ? C2 C3 C6 O1 174.9(4) . . . . ? N2 C7 C8 C12 174.7(5) . . . . ? O1 C7 C8 C12 -5.3(7) . . . . ? N2 C7 C8 C9 -4.5(8) . . . . ? O1 C7 C8 C9 175.5(4) . . . . ? C12 C8 C9 C10 -0.1(8) . . . . ? C7 C8 C9 C10 179.1(5) . . . . ? C8 C9 C10 N3 0.7(9) . . . . ? C9 C8 C12 C11 -0.8(8) . . . . ? C7 C8 C12 C11 -180.0(5) . . . . ? N3 C11 C12 C8 1.2(8) . . . . ? O10 C13 C14 C19 178.4(6) . . . . ? O11 C13 C14 C19 -3.4(7) . . . . ? O10 C13 C14 C15 -1.1(8) . . . . ? O11 C13 C14 C15 177.2(5) . . . . ? C19 C14 C15 C16 1.0(8) . . . . ? C13 C14 C15 C16 -179.5(5) . . . . ? C14 C15 C16 C17 -1.2(9) . . . . ? C15 C16 C17 C18 0.2(9) . . . . ? C16 C17 C18 O12 178.1(6) . . . . ? C16 C17 C18 C19 0.9(8) . . . . ? C15 C14 C19 C18 0.1(8) . . . . ? C13 C14 C19 C18 -179.4(5) . . . . ? O12 C18 C19 C14 -178.4(5) . . . . ? C17 C18 C19 C14 -1.1(8) . . . . ? N8 C20 C21 C22 0.2(8) . . . . ? C20 C21 C22 C23 -0.6(8) . . . . ? C20 C21 C22 C25 177.5(5) . . . . ? C21 C22 C23 C24 -0.3(8) . . . . ? C25 C22 C23 C24 -178.5(5) . . . . ? C22 C23 C24 N8 1.8(8) . . . . ? C21 C22 C25 N5 -166.4(5) . . . . ? C23 C22 C25 N5 11.7(8) . . . . ? C21 C22 C25 O4 12.1(7) . . . . ? C23 C22 C25 O4 -169.8(4) . . . . ? N6 C26 C27 C28 6.6(8) . . . . ? O4 C26 C27 C28 -172.9(4) . . . . ? N6 C26 C27 C31 -171.0(5) . . . . ? O4 C26 C27 C31 9.5(7) . . . . ? C31 C27 C28 C29 -0.7(8) . . . . ? C26 C27 C28 C29 -178.4(5) . . . . ? C27 C28 C29 N7 -0.9(9) . . . . ? N7 C30 C31 C27 -0.9(8) . . . . ? C28 C27 C31 C30 1.6(8) . . . . ? C26 C27 C31 C30 179.2(5) . . . . ? O9 C32 C33 C34 -179.5(5) . . . . ? C37 C32 C33 C34 1.2(8) . . . . ? C32 C33 C34 C35 -0.5(8) . . . . ? C33 C34 C35 C36 0.2(9) . . . . ? C34 C35 C36 C37 -0.6(8) . . . . ? C34 C35 C36 C38 178.4(5) . . . . ? C35 C36 C37 C32 1.2(7) . . . . ? C38 C36 C37 C32 -177.7(5) . . . . ? C33 C32 C37 C36 -1.5(8) . . . . ? O9 C32 C37 C36 179.1(5) . . . . ? C37 C36 C38 O8 174.9(5) . . . . ? C35 C36 C38 O8 -4.0(8) . . . . ? C37 C36 C38 O7 -4.8(7) . . . . ? C35 C36 C38 O7 176.3(5) . . . . ? O1 C6 N1 N2 0.7(6) . . . . ? C3 C6 N1 N2 179.5(5) . . . . ? O1 C7 N2 N1 1.0(6) . . . . ? C8 C7 N2 N1 -179.1(5) . . . . ? C6 N1 N2 C7 -1.0(6) . . . . ? C9 C10 N3 O2 -179.0(5) . . . . ? C9 C10 N3 C11 -0.4(8) . . . . ? C12 C11 N3 O2 178.1(5) . . . . ? C12 C11 N3 C10 -0.5(8) . . . . ? C2 C1 N4 O3 178.2(5) . . . . ? C2 C1 N4 C5 -1.4(8) . . . . ? C4 C5 N4 O3 -177.5(5) . . . . ? C4 C5 N4 C1 2.1(8) . . . . ? O4 C25 N5 N6 0.4(5) . . . . ? C22 C25 N5 N6 179.0(5) . . . . ? O4 C26 N6 N5 -0.9(6) . . . . ? C27 C26 N6 N5 179.7(5) . . . . ? C25 N5 N6 C26 0.2(5) . . . . ? C31 C30 N7 O5 -177.6(5) . . . . ? C31 C30 N7 C29 -0.7(8) . . . . ? C28 C29 N7 O5 178.5(5) . . . . ? C28 C29 N7 C30 1.6(8) . . . . ? C21 C20 N8 O6 -177.5(5) . . . . ? C21 C20 N8 C24 1.2(8) . . . . ? C23 C24 N8 C20 -2.2(8) . . . . ? C23 C24 N8 O6 176.4(5) . . . . ? N2 C7 O1 C6 -0.5(6) . . . . ? C8 C7 O1 C6 179.5(4) . . . . ? N1 C6 O1 C7 -0.2(6) . . . . ? C3 C6 O1 C7 -179.1(4) . . . . ? N6 C26 O4 C25 1.1(5) . . . . ? C27 C26 O4 C25 -179.4(4) . . . . ? N5 C25 O4 C26 -0.9(5) . . . . ? C22 C25 O4 C26 -179.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7 O6 0.82 1.75 2.563(5) 169.5 1_556 O11 H11A N4 0.82 2.64 3.452(6) 169.2 2_565 O11 H11A O3 0.82 1.76 2.559(5) 163.2 2_565 O9 H9A O5 0.82 1.82 2.620(5) 164.5 . O12 H12A O2 0.82 1.82 2.603(5) 157.9 2_564 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.204 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.040 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 735626' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 N4 O7' _chemical_formula_sum 'C19 H14 N4 O7' _chemical_formula_weight 410.34 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 10.686(2) _cell_length_b 7.0251(16) _cell_length_c 23.755(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.459(4) _cell_angle_gamma 90.00 _cell_volume 1759.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1185 _cell_measurement_theta_min 2.245 _cell_measurement_theta_max 20.806 _exptl_crystal_description BAR _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8530 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3102 _reflns_number_gt 2052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1241P)^2^+1.9734P] 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_number_reflns 3102 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2390 _refine_ls_wR_factor_gt 0.2141 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 -0.2466(4) 0.4567(6) 0.87770(18) 0.0427(11) Uani 1 1 d . . . H1 H -0.3069 0.4071 0.8978 0.051 Uiso 1 1 calc R . . C2 C -0.1316(4) 0.5115(6) 0.90637(17) 0.0384(10) Uani 1 1 d . . . H2 H -0.1136 0.5004 0.9459 0.046 Uiso 1 1 calc R . . C3 C -0.0409(4) 0.5844(5) 0.87641(16) 0.0319(9) Uani 1 1 d . . . C4 C -0.0711(4) 0.5995(6) 0.81761(17) 0.0370(10) Uani 1 1 d . . . H4 H -0.0119 0.6477 0.7967 0.044 Uiso 1 1 calc R . . C5 C -0.1880(4) 0.5437(6) 0.79042(17) 0.0389(10) Uani 1 1 d . . . H5 H -0.2080 0.5544 0.7509 0.047 Uiso 1 1 calc R . . C6 C 0.0831(4) 0.6413(6) 0.90699(17) 0.0349(9) Uani 1 1 d . . . C7 C 0.2749(4) 0.7264(6) 0.91801(18) 0.0373(10) Uani 1 1 d . . . C8 C 0.3934(4) 0.7845(6) 0.90078(17) 0.0364(10) Uani 1 1 d . . . C9 C 0.4047(4) 0.8005(6) 0.84389(18) 0.0395(10) Uani 1 1 d . . . H9 H 0.3365 0.7702 0.8157 0.047 Uiso 1 1 calc R . . C10 C 0.5163(4) 0.8609(6) 0.82920(18) 0.0426(11) Uani 1 1 d . . . H10 H 0.5234 0.8700 0.7908 0.051 Uiso 1 1 calc R . . C11 C 0.6078(4) 0.8907(8) 0.9245(2) 0.0564(13) Uani 1 1 d . . . H11 H 0.6774 0.9215 0.9519 0.068 Uiso 1 1 calc R . . C12 C 0.4988(4) 0.8290(8) 0.9413(2) 0.0527(13) Uani 1 1 d . . . H12 H 0.4948 0.8167 0.9799 0.063 Uiso 1 1 calc R . . C13 C 0.0226(4) 0.1012(6) 0.89726(17) 0.0352(9) Uani 1 1 d . . . C14 C 0.0166(4) 0.0838(6) 0.83792(19) 0.0444(11) Uani 1 1 d . . . H14 H -0.0571 0.0389 0.8155 0.053 Uiso 1 1 calc R . . C15 C 0.1184(4) 0.1324(7) 0.8130(2) 0.0483(11) Uani 1 1 d . . . H15 H 0.1142 0.1161 0.7739 0.058 Uiso 1 1 calc R . . C16 C 0.2264(4) 0.2045(6) 0.84443(18) 0.0409(10) Uani 1 1 d . . . C17 C 0.3374(5) 0.2557(7) 0.8150(2) 0.0489(12) Uani 1 1 d . . . C18 C 0.2343(4) 0.2250(6) 0.9031(2) 0.0468(12) Uani 1 1 d . . . H18 H 0.3078 0.2737 0.9247 0.056 Uiso 1 1 calc R . . C19 C 0.1319(4) 0.1726(6) 0.92988(18) 0.0415(10) Uani 1 1 d . . . N1 N -0.2745(3) 0.4734(5) 0.82003(14) 0.0381(8) Uani 1 1 d . . . N2 N 0.1192(3) 0.6589(6) 0.96098(15) 0.0475(10) Uani 1 1 d . . . N3 N 0.2467(3) 0.7137(6) 0.96852(15) 0.0486(10) Uani 1 1 d . . . N4 N 0.6160(3) 0.9075(5) 0.86891(15) 0.0435(9) Uani 1 1 d . . . O1 O -0.3868(3) 0.4226(5) 0.79261(13) 0.0564(9) Uani 1 1 d . . . O2 O 0.1759(2) 0.6828(4) 0.87673(11) 0.0340(7) Uani 1 1 d . . . O3 O 0.7208(3) 0.9671(6) 0.85258(14) 0.0630(10) Uani 1 1 d . . . O4 O -0.0726(3) 0.0506(5) 0.92476(12) 0.0467(8) Uani 1 1 d . . . H4A H -0.1360 0.0259 0.9014 0.070 Uiso 1 1 calc R . . O5 O 0.1399(3) 0.1948(7) 0.98592(15) 0.0737(12) Uani 1 1 d . . . H5A H 0.0707 0.1727 0.9952 0.111 Uiso 1 1 calc R . . O6 O 0.4337(3) 0.3211(5) 0.84976(16) 0.0667(10) Uani 1 1 d . . . H6 H 0.4911 0.3467 0.8319 0.100 Uiso 1 1 calc R . . O7 O 0.3345(3) 0.2318(6) 0.76451(16) 0.0726(11) 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 0.038(2) 0.055(3) 0.037(2) 0.005(2) 0.0130(19) -0.008(2) C2 0.042(2) 0.049(2) 0.025(2) 0.0016(18) 0.0077(17) -0.006(2) C3 0.032(2) 0.033(2) 0.031(2) 0.0010(17) 0.0062(16) -0.0006(17) C4 0.034(2) 0.047(2) 0.033(2) 0.0024(19) 0.0113(17) -0.0059(18) C5 0.032(2) 0.056(3) 0.029(2) 0.0071(19) 0.0060(17) -0.0010(19) C6 0.039(2) 0.035(2) 0.033(2) 0.0009(18) 0.0113(18) -0.0035(18) C7 0.035(2) 0.040(2) 0.035(2) 0.0019(19) 0.0020(18) -0.0022(18) C8 0.032(2) 0.040(2) 0.037(2) -0.0020(19) 0.0053(18) -0.0005(18) C9 0.032(2) 0.048(2) 0.036(2) -0.007(2) -0.0012(18) -0.0032(19) C10 0.035(2) 0.059(3) 0.035(2) -0.001(2) 0.0063(18) -0.002(2) C11 0.037(2) 0.093(4) 0.037(3) -0.001(3) -0.002(2) -0.014(2) C12 0.040(3) 0.082(4) 0.036(2) 0.001(2) 0.004(2) -0.008(2) C13 0.034(2) 0.035(2) 0.038(2) 0.0040(18) 0.0098(18) -0.0015(17) C14 0.043(2) 0.050(3) 0.044(3) 0.007(2) 0.016(2) 0.006(2) C15 0.052(3) 0.053(3) 0.041(3) 0.006(2) 0.010(2) 0.005(2) C16 0.051(3) 0.032(2) 0.042(3) 0.0062(19) 0.015(2) 0.004(2) C17 0.054(3) 0.052(3) 0.039(3) 0.006(2) 0.005(2) 0.011(2) C18 0.032(2) 0.039(2) 0.066(3) -0.005(2) -0.001(2) -0.0042(19) C19 0.043(2) 0.047(3) 0.034(2) -0.007(2) 0.0066(19) -0.004(2) N1 0.0297(18) 0.048(2) 0.037(2) -0.0006(16) 0.0073(15) -0.0029(15) N2 0.044(2) 0.066(3) 0.033(2) 0.0030(18) 0.0064(16) -0.0148(19) N3 0.043(2) 0.070(3) 0.032(2) 0.0010(18) 0.0042(17) -0.0151(19) N4 0.0258(18) 0.060(2) 0.045(2) -0.0025(19) 0.0067(16) -0.0027(17) O1 0.0304(16) 0.095(3) 0.0436(18) -0.0005(17) 0.0044(13) -0.0167(16) O2 0.0310(14) 0.0425(16) 0.0286(14) 0.0012(12) 0.0050(12) -0.0048(12) O3 0.0333(17) 0.103(3) 0.053(2) 0.0047(19) 0.0092(15) -0.0168(17) O4 0.0352(16) 0.066(2) 0.0410(17) 0.0026(16) 0.0132(13) -0.0077(15) O5 0.064(2) 0.108(3) 0.050(2) -0.007(2) 0.0127(18) -0.021(2) O6 0.050(2) 0.076(2) 0.075(3) -0.008(2) 0.0141(19) -0.0190(18) O7 0.055(2) 0.116(3) 0.049(2) 0.008(2) 0.0146(17) -0.009(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 C1 N1 1.358(5) . ? C1 C2 1.360(6) . ? C1 H1 0.9300 . ? C2 C3 1.391(5) . ? C2 H2 0.9300 . ? C3 C4 1.385(5) . ? C3 C6 1.458(5) . ? C4 C5 1.367(6) . ? C4 H4 0.9300 . ? C5 N1 1.344(5) . ? C5 H5 0.9300 . ? C6 N2 1.283(5) . ? C6 O2 1.348(5) . ? C7 N3 1.288(5) . ? C7 O2 1.355(5) . ? C7 C8 1.451(6) . ? C8 C9 1.381(6) . ? C8 C12 1.392(6) . ? C9 C10 1.363(6) . ? C9 H9 0.9300 . ? C10 N4 1.343(5) . ? C10 H10 0.9300 . ? C11 N4 1.343(6) . ? C11 C12 1.362(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O4 1.344(5) . ? C13 C19 1.386(6) . ? C13 C14 1.406(6) . ? C14 C15 1.365(6) . ? C14 H14 0.9300 . ? C15 C16 1.364(6) . ? C15 H15 0.9300 . ? C16 C18 1.390(6) . ? C16 C17 1.515(6) . ? C17 O7 1.207(6) . ? C17 O6 1.294(6) . ? C18 C19 1.402(6) . ? C18 H18 0.9300 . ? C19 O5 1.329(5) . ? N1 O1 1.317(4) . ? N2 N3 1.398(5) . ? N4 O3 1.312(4) . ? O4 H4A 0.8200 . ? O5 H5A 0.8200 . ? O6 H6 0.8200 . ? 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 N1 C1 C2 120.7(4) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 119.8(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 118.5(4) . . ? C4 C3 C6 121.6(4) . . ? C2 C3 C6 119.9(4) . . ? C5 C4 C3 119.9(4) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 120.8(4) . . ? N1 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? N2 C6 O2 112.7(4) . . ? N2 C6 C3 128.6(4) . . ? O2 C6 C3 118.7(3) . . ? N3 C7 O2 112.6(3) . . ? N3 C7 C8 129.1(4) . . ? O2 C7 C8 118.3(4) . . ? C9 C8 C12 117.8(4) . . ? C9 C8 C7 121.3(4) . . ? C12 C8 C7 120.8(4) . . ? C10 C9 C8 119.8(4) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N4 C10 C9 121.5(4) . . ? N4 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? N4 C11 C12 120.9(4) . . ? N4 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C8 120.2(4) . . ? C11 C12 H12 119.9 . . ? C8 C12 H12 119.9 . . ? O4 C13 C19 117.4(4) . . ? O4 C13 C14 123.4(4) . . ? C19 C13 C14 119.2(4) . . ? C15 C14 C13 120.3(4) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 121.2(4) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C18 119.6(4) . . ? C15 C16 C17 119.4(4) . . ? C18 C16 C17 121.0(4) . . ? O7 C17 O6 124.8(5) . . ? O7 C17 C16 122.1(5) . . ? O6 C17 C16 113.1(4) . . ? C16 C18 C19 120.3(4) . . ? C16 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? O5 C19 C13 120.8(4) . . ? O5 C19 C18 119.8(4) . . ? C13 C19 C18 119.4(4) . . ? O1 N1 C5 119.3(3) . . ? O1 N1 C1 120.4(3) . . ? C5 N1 C1 120.2(3) . . ? C6 N2 N3 106.3(3) . . ? C7 N3 N2 105.8(3) . . ? O3 N4 C10 119.2(4) . . ? O3 N4 C11 121.0(3) . . ? C10 N4 C11 119.8(4) . . ? C6 O2 C7 102.6(3) . . ? C13 O4 H4A 109.5 . . ? C19 O5 H5A 109.5 . . ? C17 O6 H6 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.5(7) . . . . ? C1 C2 C3 C4 0.2(6) . . . . ? C1 C2 C3 C6 -179.3(4) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? C6 C3 C4 C5 179.6(4) . . . . ? C3 C4 C5 N1 -0.1(6) . . . . ? C4 C3 C6 N2 170.1(4) . . . . ? C2 C3 C6 N2 -10.4(7) . . . . ? C4 C3 C6 O2 -9.8(6) . . . . ? C2 C3 C6 O2 169.6(4) . . . . ? N3 C7 C8 C9 -176.2(4) . . . . ? O2 C7 C8 C9 1.8(6) . . . . ? N3 C7 C8 C12 2.7(7) . . . . ? O2 C7 C8 C12 -179.3(4) . . . . ? C12 C8 C9 C10 -0.9(6) . . . . ? C7 C8 C9 C10 178.0(4) . . . . ? C8 C9 C10 N4 -0.7(7) . . . . ? N4 C11 C12 C8 -0.8(8) . . . . ? C9 C8 C12 C11 1.6(7) . . . . ? C7 C8 C12 C11 -177.4(5) . . . . ? O4 C13 C14 C15 -178.0(4) . . . . ? C19 C13 C14 C15 1.6(6) . . . . ? C13 C14 C15 C16 -2.2(7) . . . . ? C14 C15 C16 C18 1.5(7) . . . . ? C14 C15 C16 C17 179.7(4) . . . . ? C15 C16 C17 O7 -1.3(7) . . . . ? C18 C16 C17 O7 176.9(5) . . . . ? C15 C16 C17 O6 -179.6(4) . . . . ? C18 C16 C17 O6 -1.4(6) . . . . ? C15 C16 C18 C19 -0.2(7) . . . . ? C17 C16 C18 C19 -178.4(4) . . . . ? O4 C13 C19 O5 -1.9(6) . . . . ? C14 C13 C19 O5 178.6(4) . . . . ? O4 C13 C19 C18 179.2(4) . . . . ? C14 C13 C19 C18 -0.3(6) . . . . ? C16 C18 C19 O5 -179.3(4) . . . . ? C16 C18 C19 C13 -0.3(6) . . . . ? C4 C5 N1 O1 179.3(4) . . . . ? C4 C5 N1 C1 -0.1(6) . . . . ? C2 C1 N1 O1 -179.0(4) . . . . ? C2 C1 N1 C5 0.4(6) . . . . ? O2 C6 N2 N3 -1.0(5) . . . . ? C3 C6 N2 N3 179.1(4) . . . . ? O2 C7 N3 N2 -0.5(5) . . . . ? C8 C7 N3 N2 177.6(4) . . . . ? C6 N2 N3 C7 0.9(5) . . . . ? C9 C10 N4 O3 -179.2(4) . . . . ? C9 C10 N4 C11 1.5(7) . . . . ? C12 C11 N4 O3 179.9(5) . . . . ? C12 C11 N4 C10 -0.8(8) . . . . ? N2 C6 O2 C7 0.7(4) . . . . ? C3 C6 O2 C7 -179.4(3) . . . . ? N3 C7 O2 C6 -0.1(4) . . . . ? C8 C7 O2 C6 -178.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O4 0.82 2.46 2.914(5) 115.7 3_557 O4 H4A O3 0.82 1.81 2.629(4) 177.3 1_445 O5 H5A O4 0.82 2.24 2.685(5) 114.1 . O6 H6 O1 0.82 1.81 2.624(5) 175.4 1_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.176 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.078 # Attachment '4.cif' #========================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 735627' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H15 N5 O5' _chemical_formula_sum 'C19 H15 N5 O5' _chemical_formula_weight 393.36 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.037(3) _cell_length_b 7.1184(19) _cell_length_c 11.835(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.271(4) _cell_angle_gamma 90.00 _cell_volume 882.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1014 _cell_measurement_theta_min 2.203 _cell_measurement_theta_max 26.923 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4598 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1778 _reflns_number_gt 1286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0287P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 1778 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.000 _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 0.3845(3) -0.1915(5) 0.2365(3) 0.0452(10) Uani 1 1 d . . . H1 H 0.3063 -0.2442 0.1941 0.054 Uiso 1 1 calc R . . C2 C 0.4656(3) -0.1313(5) 0.1781(3) 0.0428(9) Uani 1 1 d . . . H2 H 0.4425 -0.1443 0.0959 0.051 Uiso 1 1 calc R . . C3 C 0.5816(3) -0.0510(5) 0.2389(3) 0.0336(9) Uani 1 1 d . . . C4 C 0.6137(3) -0.0387(5) 0.3614(3) 0.0402(9) Uani 1 1 d . . . H4 H 0.6924 0.0108 0.4053 0.048 Uiso 1 1 calc R . . C5 C 0.5305(3) -0.0987(5) 0.4183(3) 0.0424(10) Uani 1 1 d . . . H5 H 0.5521 -0.0870 0.5005 0.051 Uiso 1 1 calc R . . C6 C 0.6668(3) 0.0167(5) 0.1773(3) 0.0354(8) Uani 1 1 d . . . C7 C 0.8416(3) 0.1082(5) 0.1558(3) 0.0349(8) Uani 1 1 d . . . C8 C 0.9750(3) 0.1599(4) 0.1912(3) 0.0353(9) Uani 1 1 d . . . C9 C 1.0293(3) 0.2289(6) 0.1103(3) 0.0501(11) Uani 1 1 d . . . H9 H 0.9797 0.2423 0.0312 0.060 Uiso 1 1 calc R . . C10 C 1.1550(3) 0.2782(6) 0.1441(3) 0.0526(11) Uani 1 1 d . . . H10 H 1.1896 0.3260 0.0878 0.063 Uiso 1 1 calc R . . C11 C 1.1766(3) 0.1949(5) 0.3386(3) 0.0518(11) Uani 1 1 d . . . H11 H 1.2271 0.1846 0.4177 0.062 Uiso 1 1 calc R . . C12 C 1.0511(3) 0.1451(5) 0.3077(3) 0.0467(10) Uani 1 1 d . . . H12 H 1.0170 0.1011 0.3653 0.056 Uiso 1 1 calc R . . C13 C 0.6965(3) 0.4889(5) 0.2847(3) 0.0399(9) Uani 1 1 d . . . C14 C 0.6542(3) 0.5185(5) 0.1625(3) 0.0468(10) Uani 1 1 d . . . H14 H 0.5699 0.4916 0.1193 0.056 Uiso 1 1 calc R . . C15 C 0.7344(4) 0.5864(6) 0.1052(3) 0.0530(10) Uani 1 1 d . . . H15 H 0.7038 0.6070 0.0235 0.064 Uiso 1 1 calc R . . C16 C 0.8605(3) 0.6251(5) 0.1665(3) 0.0450(9) Uani 1 1 d . . . H16 H 0.9144 0.6728 0.1268 0.054 Uiso 1 1 calc R . . C17 C 0.9056(3) 0.5924(5) 0.2875(3) 0.0354(8) Uani 1 1 d . . . C18 C 0.8243(3) 0.5229(5) 0.3454(3) 0.0390(9) Uani 1 1 d . . . H18 H 0.8557 0.4985 0.4266 0.047 Uiso 1 1 calc R . . C19 C 1.0404(3) 0.6292(5) 0.3559(3) 0.0413(9) Uani 1 1 d . . . N1 N 0.7605(3) 0.1007(4) 0.0499(2) 0.0446(8) Uani 1 1 d . . . N2 N 0.6449(2) 0.0397(4) 0.0645(2) 0.0470(8) Uani 1 1 d . . . N3 N 0.4174(3) -0.1749(4) 0.3563(2) 0.0413(8) Uani 1 1 d . . . N4 N 1.2293(3) 0.2587(4) 0.2575(3) 0.0501(8) Uani 1 1 d . . . N5 N 0.6143(3) 0.4310(5) 0.3434(3) 0.0656(11) Uani 1 1 d . . . O1 O 0.3399(2) -0.2327(4) 0.41380(19) 0.0588(8) Uani 1 1 d . . . O2 O 1.3481(2) 0.3042(4) 0.2887(2) 0.0778(10) Uani 1 1 d . . . O3 O 0.78953(19) 0.0554(3) 0.24106(17) 0.0364(6) Uani 1 1 d . . . O4 O 1.0828(2) 0.6145(4) 0.46336(19) 0.0675(9) Uani 1 1 d . . . O5 O 1.1111(2) 0.6788(4) 0.2901(2) 0.0604(8) Uani 1 1 d . . . H5A H 1.2008 0.7120 0.3431 0.072 Uiso 1 1 d R . . H1B H 0.6450 0.3892 0.4158 0.072 Uiso 1 1 d R . . H1A H 0.5402 0.4069 0.2992 0.072 Uiso 1 1 d 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 C1 0.029(2) 0.060(3) 0.0388(19) -0.002(2) -0.0001(18) -0.009(2) C2 0.036(2) 0.058(2) 0.0288(18) -0.0016(18) 0.0021(18) -0.005(2) C3 0.0228(19) 0.041(2) 0.0328(18) -0.0014(16) 0.0031(17) 0.0022(17) C4 0.026(2) 0.049(2) 0.043(2) -0.0069(18) 0.0069(18) -0.0052(18) C5 0.029(2) 0.060(3) 0.0328(19) -0.0057(17) 0.0016(18) -0.0036(19) C6 0.024(2) 0.038(2) 0.0380(19) -0.0030(18) 0.0005(17) -0.0034(18) C7 0.031(2) 0.041(2) 0.0325(18) 0.0011(17) 0.0094(17) 0.0030(17) C8 0.029(2) 0.043(2) 0.0333(18) 0.0002(17) 0.0091(17) 0.0040(18) C9 0.036(2) 0.076(3) 0.0377(19) -0.004(2) 0.0110(19) -0.003(2) C10 0.042(2) 0.078(3) 0.043(2) -0.004(2) 0.022(2) -0.009(2) C11 0.037(2) 0.071(3) 0.046(2) 0.007(2) 0.012(2) -0.003(2) C12 0.039(2) 0.054(3) 0.049(2) 0.007(2) 0.016(2) -0.004(2) C13 0.030(2) 0.038(2) 0.052(2) 0.0003(18) 0.0131(19) 0.0043(18) C14 0.034(2) 0.050(3) 0.049(2) -0.005(2) 0.0021(19) 0.000(2) C15 0.054(3) 0.060(3) 0.0395(19) 0.003(2) 0.007(2) -0.002(2) C16 0.042(2) 0.050(2) 0.044(2) 0.0042(19) 0.0147(19) -0.003(2) C17 0.029(2) 0.035(2) 0.0395(19) -0.0047(17) 0.0078(18) 0.0023(17) C18 0.033(2) 0.045(2) 0.0361(17) -0.0038(17) 0.0055(17) 0.0009(19) C19 0.036(2) 0.044(2) 0.043(2) -0.0034(19) 0.0118(19) 0.0017(19) N1 0.0330(17) 0.060(2) 0.0394(16) 0.0020(15) 0.0091(15) -0.0037(16) N2 0.0326(18) 0.067(2) 0.0367(16) 0.0018(16) 0.0032(15) -0.0067(17) N3 0.0250(16) 0.056(2) 0.0412(17) 0.0019(16) 0.0076(15) 0.0004(16) N4 0.0294(19) 0.067(2) 0.0545(19) -0.0093(17) 0.0137(17) -0.0070(17) N5 0.038(2) 0.089(3) 0.070(2) 0.010(2) 0.0156(19) -0.0082(19) O1 0.0322(14) 0.097(2) 0.0483(14) 0.0027(14) 0.0143(13) -0.0188(15) O2 0.0357(17) 0.118(3) 0.081(2) -0.007(2) 0.0187(16) -0.0224(18) O3 0.0294(13) 0.0466(15) 0.0318(11) -0.0014(11) 0.0076(11) -0.0028(11) O4 0.0386(15) 0.115(3) 0.0446(14) -0.0032(17) 0.0061(13) -0.0111(17) O5 0.0362(15) 0.091(2) 0.0555(15) -0.0012(15) 0.0160(14) -0.0172(15) _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 N3 1.354(4) . ? C1 C2 1.361(4) . ? C1 H1 0.9300 . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 C6 1.441(4) . ? C4 C5 1.366(4) . ? C4 H4 0.9300 . ? C5 N3 1.347(4) . ? C5 H5 0.9300 . ? C6 N2 1.290(4) . ? C6 O3 1.356(3) . ? C7 N1 1.293(4) . ? C7 O3 1.362(3) . ? C7 C8 1.446(4) . ? C8 C9 1.370(4) . ? C8 C12 1.375(4) . ? C9 C10 1.363(4) . ? C9 H9 0.9300 . ? C10 N4 1.343(4) . ? C10 H10 0.9300 . ? C11 N4 1.347(4) . ? C11 C12 1.365(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N5 1.368(4) . ? C13 C18 1.389(4) . ? C13 C14 1.389(4) . ? C14 C15 1.362(5) . ? C14 H14 0.9300 . ? C15 C16 1.381(5) . ? C15 H15 0.9300 . ? C16 C17 1.380(4) . ? C16 H16 0.9300 . ? C17 C18 1.380(4) . ? C17 C19 1.478(4) . ? C18 H18 0.9300 . ? C19 O4 1.214(3) . ? C19 O5 1.312(4) . ? N1 N2 1.409(3) . ? N3 O1 1.315(3) . ? N4 O2 1.288(3) . ? N5 H1B 0.8688 . ? N5 H1A 0.8393 . ? O5 H5A 1.0202 . ? 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 N3 C1 C2 120.1(3) . . ? N3 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C1 C2 C3 121.1(3) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 117.6(3) . . ? C2 C3 C6 121.3(3) . . ? C4 C3 C6 121.1(3) . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N3 C5 C4 120.6(3) . . ? N3 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N2 C6 O3 112.4(3) . . ? N2 C6 C3 128.7(3) . . ? O3 C6 C3 118.8(3) . . ? N1 C7 O3 112.5(3) . . ? N1 C7 C8 128.6(3) . . ? O3 C7 C8 118.9(3) . . ? C9 C8 C12 117.7(3) . . ? C9 C8 C7 121.2(3) . . ? C12 C8 C7 121.2(3) . . ? C10 C9 C8 121.1(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? N4 C10 C9 120.8(3) . . ? N4 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? N4 C11 C12 121.7(3) . . ? N4 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C11 C12 C8 119.9(3) . . ? C11 C12 H12 120.0 . . ? C8 C12 H12 120.0 . . ? N5 C13 C18 121.2(3) . . ? N5 C13 C14 120.9(3) . . ? C18 C13 C14 117.9(3) . . ? C15 C14 C13 120.9(3) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 121.0(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 119.2(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 C19 120.8(3) . . ? C18 C17 C19 119.4(3) . . ? C17 C18 C13 121.2(3) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? O4 C19 O5 122.7(3) . . ? O4 C19 C17 123.4(3) . . ? O5 C19 C17 114.0(3) . . ? C7 N1 N2 105.8(3) . . ? C6 N2 N1 106.4(3) . . ? O1 N3 C5 119.1(2) . . ? O1 N3 C1 120.6(3) . . ? C5 N3 C1 120.3(3) . . ? O2 N4 C10 120.6(3) . . ? O2 N4 C11 120.6(3) . . ? C10 N4 C11 118.9(3) . . ? C13 N5 H1B 119.3 . . ? C13 N5 H1A 114.7 . . ? H1B N5 H1A 123.1 . . ? C6 O3 C7 102.9(2) . . ? C19 O5 H5A 109.9 . . ? 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 N3 C1 C2 C3 -0.6(6) . . . . ? C1 C2 C3 C4 1.6(5) . . . . ? C1 C2 C3 C6 -178.7(3) . . . . ? C2 C3 C4 C5 -2.1(5) . . . . ? C6 C3 C4 C5 178.2(3) . . . . ? C3 C4 C5 N3 1.6(5) . . . . ? C2 C3 C6 N2 10.9(6) . . . . ? C4 C3 C6 N2 -169.4(4) . . . . ? C2 C3 C6 O3 -165.6(3) . . . . ? C4 C3 C6 O3 14.1(5) . . . . ? N1 C7 C8 C9 6.9(6) . . . . ? O3 C7 C8 C9 -174.5(3) . . . . ? N1 C7 C8 C12 -174.3(4) . . . . ? O3 C7 C8 C12 4.2(5) . . . . ? C12 C8 C9 C10 1.0(5) . . . . ? C7 C8 C9 C10 179.7(4) . . . . ? C8 C9 C10 N4 0.7(6) . . . . ? N4 C11 C12 C8 -0.2(6) . . . . ? C9 C8 C12 C11 -1.2(5) . . . . ? C7 C8 C12 C11 -180.0(3) . . . . ? N5 C13 C14 C15 176.2(4) . . . . ? C18 C13 C14 C15 -2.7(5) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C14 C15 C16 C17 0.7(6) . . . . ? C15 C16 C17 C18 -0.4(5) . . . . ? C15 C16 C17 C19 179.0(3) . . . . ? C16 C17 C18 C13 -1.4(5) . . . . ? C19 C17 C18 C13 179.1(3) . . . . ? N5 C13 C18 C17 -176.0(3) . . . . ? C14 C13 C18 C17 3.0(5) . . . . ? C16 C17 C19 O4 175.0(4) . . . . ? C18 C17 C19 O4 -5.6(5) . . . . ? C16 C17 C19 O5 -5.2(5) . . . . ? C18 C17 C19 O5 174.2(3) . . . . ? O3 C7 N1 N2 0.4(4) . . . . ? C8 C7 N1 N2 179.0(3) . . . . ? O3 C6 N2 N1 -0.7(4) . . . . ? C3 C6 N2 N1 -177.4(3) . . . . ? C7 N1 N2 C6 0.2(4) . . . . ? C4 C5 N3 O1 179.5(3) . . . . ? C4 C5 N3 C1 -0.5(5) . . . . ? C2 C1 N3 O1 -180.0(3) . . . . ? C2 C1 N3 C5 0.0(6) . . . . ? C9 C10 N4 O2 179.5(4) . . . . ? C9 C10 N4 C11 -2.1(6) . . . . ? C12 C11 N4 O2 -179.7(3) . . . . ? C12 C11 N4 C10 1.9(6) . . . . ? N2 C6 O3 C7 1.0(4) . . . . ? C3 C6 O3 C7 178.0(3) . . . . ? N1 C7 O3 C6 -0.8(4) . . . . ? C8 C7 O3 C6 -179.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H1B O1 0.87 2.15 2.993(4) 162.4 2_656 N5 H1A O2 0.84 2.21 2.945(4) 146.5 1_455 O5 H5A O1 1.02 1.55 2.569(3) 175.0 1_665 O5 H5A N3 1.02 2.48 3.387(4) 147.6 1_665 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.127 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.037 # Attachment '5.cif' #========================================================================== data_5 _database_code_depnum_ccdc_archive 'CCDC 735628' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H30 N8 O13' _chemical_formula_sum 'C36 H30 N8 O13' _chemical_formula_weight 782.68 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 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 11.449(5) _cell_length_b 7.804(3) _cell_length_c 38.548(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.216(6) _cell_angle_gamma 90.00 _cell_volume 3417(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2957 _cell_measurement_theta_min 2.819 _cell_measurement_theta_max 23.939 _exptl_crystal_description plan _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17471 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 46 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.50 _reflns_number_total 6328 _reflns_number_gt 4046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0607P)^2^+0.2685P] 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_number_reflns 6328 _refine_ls_number_parameters 520 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.0913(2) 0.8480(3) 0.52415(6) 0.0540(7) Uani 1 1 d . . . H1 H 0.0770 0.8335 0.5472 0.065 Uiso 1 1 calc R . . C2 C 0.0343(2) 0.7488(3) 0.49867(5) 0.0472(6) Uani 1 1 d . . . H2 H -0.0198 0.6677 0.5042 0.057 Uiso 1 1 calc R . . C3 C 0.0563(2) 0.7672(3) 0.46418(5) 0.0399(5) Uani 1 1 d . . . C4 C 0.1370(2) 0.8878(3) 0.45708(6) 0.0503(6) Uani 1 1 d . . . H4 H 0.1544 0.9018 0.4343 0.060 Uiso 1 1 calc R . . C5 C 0.1919(2) 0.9873(4) 0.48340(7) 0.0620(7) Uani 1 1 d . . . H5 H 0.2460 1.0696 0.4784 0.074 Uiso 1 1 calc R . . C6 C -0.0063(2) 0.6594(3) 0.43744(5) 0.0377(5) Uani 1 1 d . . . C7 C -0.06135(19) 0.5591(3) 0.38699(5) 0.0353(5) Uani 1 1 d . . . C8 C -0.06451(19) 0.5412(3) 0.34954(5) 0.0356(5) Uani 1 1 d . . . C9 C 0.0031(2) 0.6437(3) 0.33108(5) 0.0455(6) Uani 1 1 d . . . H9 H 0.0520 0.7263 0.3426 0.055 Uiso 1 1 calc R . . C10 C -0.0017(2) 0.6243(3) 0.29571(6) 0.0500(6) Uani 1 1 d . . . H10 H 0.0429 0.6953 0.2831 0.060 Uiso 1 1 calc R . . C11 C -0.1377(2) 0.4020(3) 0.29635(6) 0.0459(6) Uani 1 1 d . . . H11 H -0.1855 0.3196 0.2843 0.055 Uiso 1 1 calc R . . C12 C -0.1362(2) 0.4195(3) 0.33158(5) 0.0432(6) Uani 1 1 d . . . H12 H -0.1834 0.3496 0.3435 0.052 Uiso 1 1 calc R . . C13 C 0.27068(19) 0.3580(3) 0.15746(5) 0.0381(5) Uani 1 1 d . . . C14 C 0.33161(19) 0.2416(3) 0.18014(5) 0.0390(5) Uani 1 1 d . . . H14 H 0.3215 0.2392 0.2037 0.047 Uiso 1 1 calc R . . C15 C 0.4080(2) 0.1289(3) 0.16676(6) 0.0413(5) Uani 1 1 d . . . C16 C 0.4244(2) 0.1330(3) 0.13197(6) 0.0453(6) Uani 1 1 d . . . H16 H 0.4764 0.0573 0.1233 0.054 Uiso 1 1 calc R . . C17 C 0.3630(2) 0.2508(3) 0.11017(5) 0.0404(5) Uani 1 1 d . . . C18 C 0.28498(19) 0.3637(3) 0.12255(5) 0.0398(5) Uani 1 1 d . . . H18 H 0.2430 0.4420 0.1076 0.048 Uiso 1 1 calc R . . C19 C 0.3058(2) 0.9603(3) 0.02092(6) 0.0484(6) Uani 1 1 d . . . H19 H 0.2482 1.0360 0.0264 0.058 Uiso 1 1 calc R . . C20 C 0.3668(2) 0.8653(3) 0.04678(6) 0.0448(6) Uani 1 1 d . . . H20 H 0.3501 0.8762 0.0697 0.054 Uiso 1 1 calc R . . C21 C 0.4529(2) 0.7534(3) 0.03916(5) 0.0378(5) Uani 1 1 d . . . C22 C 0.4743(2) 0.7429(3) 0.00458(5) 0.0422(6) Uani 1 1 d . . . H22 H 0.5325 0.6695 -0.0014 0.051 Uiso 1 1 calc R . . C23 C 0.4114(2) 0.8382(3) -0.02051(5) 0.0441(6) Uani 1 1 d . . . H23 H 0.4263 0.8289 -0.0436 0.053 Uiso 1 1 calc R . . C24 C 0.5195(2) 0.6472(3) 0.06533(5) 0.0375(5) Uani 1 1 d . . . C25 C 0.57584(19) 0.5351(3) 0.11477(5) 0.0376(5) Uani 1 1 d . . . C26 C 0.58112(19) 0.5025(3) 0.15202(5) 0.0375(5) Uani 1 1 d . . . C27 C 0.5227(2) 0.6018(3) 0.17360(6) 0.0437(6) Uani 1 1 d . . . H27 H 0.4769 0.6934 0.1644 0.052 Uiso 1 1 calc R . . C28 C 0.5315(2) 0.5665(3) 0.20872(6) 0.0480(6) Uani 1 1 d . . . H28 H 0.4919 0.6346 0.2232 0.058 Uiso 1 1 calc R . . C29 C 0.6551(2) 0.3356(3) 0.20164(6) 0.0472(6) Uani 1 1 d . . . H29 H 0.7005 0.2446 0.2114 0.057 Uiso 1 1 calc R . . C30 C 0.6486(2) 0.3671(3) 0.16666(6) 0.0441(6) Uani 1 1 d . . . H30 H 0.6893 0.2978 0.1526 0.053 Uiso 1 1 calc R . . C31 C 0.1805(2) 0.2466(3) 0.32205(5) 0.0385(5) Uani 1 1 d . . . C32 C 0.2508(2) 0.3589(3) 0.34295(5) 0.0408(5) Uani 1 1 d . . . H32 H 0.3080 0.4232 0.3338 0.049 Uiso 1 1 calc R . . C33 C 0.2348(2) 0.3744(3) 0.37778(6) 0.0410(5) Uani 1 1 d . . . C34 C 0.1492(2) 0.2811(3) 0.39166(5) 0.0404(5) Uani 1 1 d . . . H34 H 0.1390 0.2921 0.4151 0.048 Uiso 1 1 calc R . . C35 C 0.0793(2) 0.1713(3) 0.37006(6) 0.0408(5) Uani 1 1 d . . . C36 C 0.0948(2) 0.1512(3) 0.33529(5) 0.0405(5) Uani 1 1 d . . . H36 H 0.0483 0.0747 0.3211 0.049 Uiso 1 1 calc R . . N1 N -0.07064(18) 0.5030(2) 0.27906(4) 0.0459(5) Uani 1 1 d . . . N2 N -0.11854(17) 0.4757(2) 0.40802(5) 0.0443(5) Uani 1 1 d . . . N3 N -0.08154(18) 0.5419(2) 0.44135(4) 0.0470(5) Uani 1 1 d . . . N4 N 0.16843(19) 0.9673(3) 0.51632(5) 0.0591(6) Uani 1 1 d . . . N5 N 0.59682(18) 0.4344(2) 0.22218(4) 0.0463(5) Uani 1 1 d . . . N6 N 0.63650(18) 0.4639(2) 0.09306(5) 0.0491(5) Uani 1 1 d . . . N7 N 0.59929(18) 0.5377(2) 0.06047(5) 0.0484(5) Uani 1 1 d . . . N8 N 0.32719(16) 0.9466(2) -0.01223(4) 0.0434(5) Uani 1 1 d . . . O1 O 0.01242(13) 0.67858(18) 0.40364(3) 0.0384(4) Uani 1 1 d . . . O2 O -0.07122(16) 0.4823(2) 0.24466(4) 0.0627(5) Uani 1 1 d . . . O3 O 0.2179(2) 1.0668(3) 0.54110(5) 0.1043(8) Uani 1 1 d . . . O4 O 0.49895(13) 0.65420(18) 0.09938(3) 0.0399(4) Uani 1 1 d . . . O5 O 0.60459(17) 0.3967(2) 0.25566(4) 0.0690(5) Uani 1 1 d . . . O6 O 0.26575(16) 1.0394(2) -0.03639(4) 0.0624(5) Uani 1 1 d . . . O7 O 0.30645(16) 0.4852(2) 0.39744(4) 0.0642(5) Uani 1 1 d . . . H7 H 0.2933 0.4800 0.4178 0.096 Uiso 1 1 calc R . . O8 O -0.00670(16) 0.0847(2) 0.38446(4) 0.0588(5) Uani 1 1 d . . . H8 H -0.0524 0.0409 0.3689 0.088 Uiso 1 1 calc R . . O9 O 0.19978(15) 0.2312(2) 0.28792(4) 0.0522(4) Uani 1 1 d . . . H9A H 0.1573 0.1557 0.2785 0.078 Uiso 1 1 calc R . . O10 O 0.38460(16) 0.2538(2) 0.07613(4) 0.0603(5) Uani 1 1 d . . . H10A H 0.3365 0.3162 0.0647 0.090 Uiso 1 1 calc R . . O11 O 0.19288(15) 0.4734(2) 0.16855(4) 0.0571(5) Uani 1 1 d . . . H11A H 0.1975 0.4706 0.1899 0.086 Uiso 1 1 calc R . . O12 O 0.47212(16) 0.0121(2) 0.18720(4) 0.0602(5) Uani 1 1 d . . . H12A H 0.4441 0.0007 0.2056 0.090 Uiso 1 1 calc R . . O13 O 0.16735(19) 0.4891(2) 0.23659(4) 0.0815(6) Uani 1 1 d . . . H13A H 0.1704 0.4114 0.2532 0.122 Uiso 1 1 d R . . H13B H 0.2437 0.5193 0.2428 0.122 Uiso 1 1 d 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 C1 0.0644(19) 0.0624(16) 0.0336(13) -0.0017(12) 0.0002(12) 0.0076(15) C2 0.0578(17) 0.0481(14) 0.0348(13) 0.0008(10) 0.0027(11) 0.0033(12) C3 0.0398(14) 0.0469(13) 0.0327(12) -0.0023(10) 0.0029(10) 0.0080(11) C4 0.0425(15) 0.0695(17) 0.0399(13) -0.0101(12) 0.0095(11) -0.0064(13) C5 0.0421(16) 0.089(2) 0.0566(17) -0.0188(15) 0.0146(13) -0.0159(14) C6 0.0405(14) 0.0447(13) 0.0285(12) 0.0001(10) 0.0072(10) 0.0055(11) C7 0.0371(13) 0.0357(12) 0.0322(12) -0.0019(9) 0.0011(10) 0.0040(10) C8 0.0412(14) 0.0355(11) 0.0299(11) 0.0026(9) 0.0037(10) 0.0105(10) C9 0.0554(16) 0.0453(14) 0.0359(13) -0.0013(10) 0.0061(11) -0.0006(12) C10 0.0621(18) 0.0491(15) 0.0400(14) 0.0065(11) 0.0116(12) 0.0009(13) C11 0.0533(16) 0.0465(14) 0.0356(13) -0.0014(11) -0.0035(11) 0.0062(12) C12 0.0493(16) 0.0429(13) 0.0366(13) 0.0037(10) 0.0030(11) 0.0032(11) C13 0.0340(13) 0.0380(12) 0.0425(13) -0.0003(10) 0.0051(10) 0.0006(10) C14 0.0422(14) 0.0414(13) 0.0335(12) 0.0007(10) 0.0056(10) -0.0035(11) C15 0.0407(14) 0.0406(13) 0.0417(13) 0.0045(10) 0.0011(10) 0.0007(11) C16 0.0433(15) 0.0490(14) 0.0434(14) -0.0051(11) 0.0045(11) 0.0052(12) C17 0.0361(14) 0.0497(14) 0.0345(12) -0.0014(10) 0.0014(10) -0.0052(11) C18 0.0380(14) 0.0429(13) 0.0374(12) 0.0020(10) -0.0001(10) 0.0024(11) C19 0.0409(15) 0.0649(16) 0.0414(13) 0.0020(12) 0.0125(11) 0.0087(12) C20 0.0464(15) 0.0582(15) 0.0310(12) -0.0005(11) 0.0095(10) 0.0007(12) C21 0.0413(14) 0.0391(12) 0.0329(12) -0.0011(9) 0.0038(10) -0.0070(11) C22 0.0504(16) 0.0433(13) 0.0336(12) -0.0038(10) 0.0082(10) 0.0026(11) C23 0.0526(16) 0.0485(14) 0.0321(12) -0.0001(10) 0.0085(11) 0.0021(12) C24 0.0401(14) 0.0408(13) 0.0324(12) -0.0027(10) 0.0071(10) -0.0066(11) C25 0.0386(14) 0.0352(12) 0.0383(12) 0.0006(10) 0.0019(10) -0.0036(10) C26 0.0394(14) 0.0386(12) 0.0339(12) -0.0017(10) 0.0028(10) -0.0088(11) C27 0.0442(15) 0.0443(13) 0.0418(13) -0.0002(10) 0.0021(11) -0.0012(11) C28 0.0524(16) 0.0532(15) 0.0377(13) -0.0084(11) 0.0026(11) 0.0013(12) C29 0.0518(16) 0.0460(14) 0.0416(14) 0.0006(11) -0.0023(11) 0.0016(12) C30 0.0455(15) 0.0458(13) 0.0401(13) -0.0023(10) 0.0021(11) -0.0018(11) C31 0.0409(14) 0.0402(12) 0.0334(12) 0.0030(10) 0.0010(10) 0.0094(11) C32 0.0386(14) 0.0417(13) 0.0419(13) -0.0006(10) 0.0041(10) -0.0020(11) C33 0.0396(14) 0.0409(13) 0.0412(13) -0.0055(10) -0.0007(10) 0.0012(11) C34 0.0422(15) 0.0449(13) 0.0337(12) -0.0017(10) 0.0028(10) 0.0020(11) C35 0.0387(14) 0.0404(12) 0.0427(13) 0.0030(10) 0.0023(11) 0.0017(11) C36 0.0418(14) 0.0388(12) 0.0391(13) -0.0043(10) -0.0020(10) 0.0010(11) N1 0.0600(14) 0.0500(12) 0.0267(10) 0.0031(9) 0.0011(9) 0.0176(11) N2 0.0517(13) 0.0489(11) 0.0333(10) -0.0001(9) 0.0093(9) -0.0036(10) N3 0.0552(14) 0.0545(12) 0.0322(10) -0.0017(9) 0.0097(9) -0.0073(10) N4 0.0484(14) 0.0835(16) 0.0430(13) -0.0202(11) -0.0037(10) -0.0003(12) N5 0.0537(13) 0.0535(12) 0.0301(10) -0.0004(9) -0.0008(9) -0.0061(10) N6 0.0604(14) 0.0499(11) 0.0380(11) 0.0033(9) 0.0100(10) 0.0059(10) N7 0.0588(14) 0.0486(12) 0.0388(11) 0.0036(9) 0.0100(9) 0.0051(11) N8 0.0427(12) 0.0523(12) 0.0344(11) 0.0058(9) 0.0023(9) -0.0005(10) O1 0.0451(10) 0.0426(8) 0.0280(8) -0.0004(6) 0.0063(7) -0.0007(7) O2 0.0898(14) 0.0744(12) 0.0229(8) 0.0001(7) 0.0040(8) 0.0228(10) O3 0.0923(17) 0.151(2) 0.0661(14) -0.0515(13) -0.0035(12) -0.0410(15) O4 0.0441(10) 0.0451(9) 0.0310(8) 0.0003(6) 0.0062(7) -0.0002(7) O5 0.0941(15) 0.0829(13) 0.0289(9) 0.0043(8) 0.0032(9) 0.0055(11) O6 0.0630(12) 0.0782(12) 0.0438(10) 0.0154(9) -0.0014(8) 0.0174(10) O7 0.0624(12) 0.0782(12) 0.0523(11) -0.0236(9) 0.0088(9) -0.0273(10) O8 0.0578(12) 0.0685(12) 0.0509(10) -0.0016(9) 0.0102(9) -0.0228(9) O9 0.0619(12) 0.0597(11) 0.0348(9) -0.0036(7) 0.0049(8) -0.0077(9) O10 0.0619(13) 0.0834(13) 0.0359(9) 0.0011(8) 0.0071(8) 0.0195(10) O11 0.0650(12) 0.0634(11) 0.0446(10) 0.0054(8) 0.0140(9) 0.0240(9) O12 0.0702(13) 0.0613(11) 0.0501(11) 0.0165(9) 0.0115(9) 0.0232(10) O13 0.1182(18) 0.0760(13) 0.0544(12) 0.0139(9) 0.0270(11) 0.0143(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 C1 N4 1.344(3) . ? C1 C2 1.352(3) . ? C1 H1 0.9300 . ? C2 C3 1.391(3) . ? C2 H2 0.9300 . ? C3 C4 1.370(3) . ? C3 C6 1.448(3) . ? C4 C5 1.366(3) . ? C4 H4 0.9300 . ? C5 N4 1.339(3) . ? C5 H5 0.9300 . ? C6 N3 1.280(3) . ? C6 O1 1.355(2) . ? C7 N2 1.282(3) . ? C7 O1 1.363(2) . ? C7 C8 1.446(3) . ? C8 C9 1.372(3) . ? C8 C12 1.382(3) . ? C9 C10 1.366(3) . ? C9 H9 0.9300 . ? C10 N1 1.343(3) . ? C10 H10 0.9300 . ? C11 N1 1.335(3) . ? C11 C12 1.363(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O11 1.372(2) . ? C13 C18 1.377(3) . ? C13 C14 1.387(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 O12 1.359(2) . ? C15 C16 1.378(3) . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 O10 1.366(2) . ? C17 C18 1.381(3) . ? C18 H18 0.9300 . ? C19 N8 1.335(3) . ? C19 C20 1.362(3) . ? C19 H19 0.9300 . ? C20 C21 1.377(3) . ? C20 H20 0.9300 . ? C21 C22 1.388(3) . ? C21 C24 1.446(3) . ? C22 C23 1.353(3) . ? C22 H22 0.9300 . ? C23 N8 1.351(3) . ? C23 H23 0.9300 . ? C24 N7 1.282(3) . ? C24 O4 1.363(2) . ? C25 N6 1.279(3) . ? C25 O4 1.363(2) . ? C25 C26 1.452(3) . ? C26 C27 1.371(3) . ? C26 C30 1.387(3) . ? C27 C28 1.373(3) . ? C27 H27 0.9300 . ? C28 N5 1.339(3) . ? C28 H28 0.9300 . ? C29 N5 1.342(3) . ? C29 C30 1.363(3) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 O9 1.367(2) . ? C31 C32 1.379(3) . ? C31 C36 1.380(3) . ? C32 C33 1.383(3) . ? C32 H32 0.9300 . ? C33 O7 1.356(3) . ? C33 C34 1.382(3) . ? C34 C35 1.379(3) . ? C34 H34 0.9300 . ? C35 O8 1.368(3) . ? C35 C36 1.383(3) . ? C36 H36 0.9300 . ? N1 O2 1.335(2) . ? N2 N3 1.400(2) . ? N4 O3 1.304(3) . ? N5 O5 1.316(2) . ? N6 N7 1.399(2) . ? N8 O6 1.312(2) . ? O7 H7 0.8200 . ? O8 H8 0.8200 . ? O9 H9A 0.8200 . ? O10 H10A 0.8200 . ? O11 H11A 0.8200 . ? O12 H12A 0.8200 . ? O13 H13A 0.8789 . ? O13 H13B 0.9080 . ? 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 N4 C1 C2 120.3(2) . . ? N4 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C1 C2 C3 120.5(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 118.0(2) . . ? C4 C3 C6 122.8(2) . . ? C2 C3 C6 119.2(2) . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N4 C5 C4 120.6(2) . . ? N4 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N3 C6 O1 112.47(18) . . ? N3 C6 C3 127.73(19) . . ? O1 C6 C3 119.8(2) . . ? N2 C7 O1 112.65(18) . . ? N2 C7 C8 129.1(2) . . ? O1 C7 C8 118.21(18) . . ? C9 C8 C12 118.6(2) . . ? C9 C8 C7 121.0(2) . . ? C12 C8 C7 120.3(2) . . ? C10 C9 C8 119.9(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N1 C10 C9 120.2(2) . . ? N1 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N1 C11 C12 120.2(2) . . ? N1 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C8 120.0(2) . . ? C11 C12 H12 120.0 . . ? C8 C12 H12 120.0 . . ? O11 C13 C18 116.39(19) . . ? O11 C13 C14 121.89(19) . . ? C18 C13 C14 121.7(2) . . ? C15 C14 C13 118.2(2) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? O12 C15 C16 116.7(2) . . ? O12 C15 C14 122.04(19) . . ? C16 C15 C14 121.2(2) . . ? C15 C16 C17 119.2(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? O10 C17 C16 117.2(2) . . ? O10 C17 C18 121.62(19) . . ? C16 C17 C18 121.2(2) . . ? C13 C18 C17 118.6(2) . . ? C13 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? N8 C19 C20 121.2(2) . . ? N8 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C19 C20 C21 120.3(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C22 117.4(2) . . ? C20 C21 C24 122.93(19) . . ? C22 C21 C24 119.7(2) . . ? C23 C22 C21 120.8(2) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? N8 C23 C22 120.4(2) . . ? N8 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? N7 C24 O4 112.32(18) . . ? N7 C24 C21 127.06(19) . . ? O4 C24 C21 120.60(19) . . ? N6 C25 O4 112.67(19) . . ? N6 C25 C26 127.7(2) . . ? O4 C25 C26 119.60(19) . . ? C27 C26 C30 118.2(2) . . ? C27 C26 C25 122.6(2) . . ? C30 C26 C25 119.2(2) . . ? C26 C27 C28 120.3(2) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? N5 C28 C27 120.3(2) . . ? N5 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? N5 C29 C30 120.7(2) . . ? N5 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C29 C30 C26 119.9(2) . . ? C29 C30 H30 120.0 . . ? C26 C30 H30 120.0 . . ? O9 C31 C32 117.7(2) . . ? O9 C31 C36 121.13(19) . . ? C32 C31 C36 121.1(2) . . ? C31 C32 C33 119.0(2) . . ? C31 C32 H32 120.5 . . ? C33 C32 H32 120.5 . . ? O7 C33 C34 121.9(2) . . ? O7 C33 C32 117.0(2) . . ? C34 C33 C32 121.1(2) . . ? C35 C34 C33 118.7(2) . . ? C35 C34 H34 120.7 . . ? C33 C34 H34 120.7 . . ? O8 C35 C34 117.1(2) . . ? O8 C35 C36 121.6(2) . . ? C34 C35 C36 121.3(2) . . ? C31 C36 C35 118.8(2) . . ? C31 C36 H36 120.6 . . ? C35 C36 H36 120.6 . . ? O2 N1 C11 119.5(2) . . ? O2 N1 C10 119.3(2) . . ? C11 N1 C10 121.17(19) . . ? C7 N2 N3 105.84(18) . . ? C6 N3 N2 106.68(17) . . ? O3 N4 C5 120.3(2) . . ? O3 N4 C1 119.0(2) . . ? C5 N4 C1 120.6(2) . . ? O5 N5 C28 121.17(19) . . ? O5 N5 C29 118.3(2) . . ? C28 N5 C29 120.6(2) . . ? C25 N6 N7 106.24(19) . . ? C24 N7 N6 106.57(17) . . ? O6 N8 C19 119.26(19) . . ? O6 N8 C23 120.85(18) . . ? C19 N8 C23 119.89(19) . . ? C6 O1 C7 102.36(16) . . ? C24 O4 C25 102.21(16) . . ? C33 O7 H7 109.5 . . ? C35 O8 H8 109.5 . . ? C31 O9 H9A 109.5 . . ? C17 O10 H10A 109.5 . . ? C13 O11 H11A 109.5 . . ? C15 O12 H12A 109.5 . . ? H13A O13 H13B 92.2 . . ? 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 N4 C1 C2 C3 1.0(4) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C6 -179.9(2) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C6 C3 C4 C5 179.1(2) . . . . ? C3 C4 C5 N4 0.6(4) . . . . ? C4 C3 C6 N3 178.8(2) . . . . ? C2 C3 C6 N3 -1.1(3) . . . . ? C4 C3 C6 O1 -1.5(3) . . . . ? C2 C3 C6 O1 178.60(19) . . . . ? N2 C7 C8 C9 179.6(2) . . . . ? O1 C7 C8 C9 -1.3(3) . . . . ? N2 C7 C8 C12 -0.4(3) . . . . ? O1 C7 C8 C12 178.73(18) . . . . ? C12 C8 C9 C10 0.1(3) . . . . ? C7 C8 C9 C10 -179.9(2) . . . . ? C8 C9 C10 N1 -1.2(3) . . . . ? N1 C11 C12 C8 -0.5(3) . . . . ? C9 C8 C12 C11 0.8(3) . . . . ? C7 C8 C12 C11 -179.26(19) . . . . ? O11 C13 C14 C15 179.66(19) . . . . ? C18 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 O12 179.3(2) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? O12 C15 C16 C17 -179.0(2) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C15 C16 C17 O10 178.1(2) . . . . ? C15 C16 C17 C18 -0.4(3) . . . . ? O11 C13 C18 C17 179.57(19) . . . . ? C14 C13 C18 C17 -0.5(3) . . . . ? O10 C17 C18 C13 -177.57(19) . . . . ? C16 C17 C18 C13 0.8(3) . . . . ? N8 C19 C20 C21 0.5(4) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C19 C20 C21 C24 -179.1(2) . . . . ? C20 C21 C22 C23 -0.7(3) . . . . ? C24 C21 C22 C23 178.6(2) . . . . ? C21 C22 C23 N8 0.6(3) . . . . ? C20 C21 C24 N7 178.6(2) . . . . ? C22 C21 C24 N7 -0.7(3) . . . . ? C20 C21 C24 O4 0.0(3) . . . . ? C22 C21 C24 O4 -179.25(18) . . . . ? N6 C25 C26 C27 171.4(2) . . . . ? O4 C25 C26 C27 -8.6(3) . . . . ? N6 C25 C26 C30 -7.9(3) . . . . ? O4 C25 C26 C30 172.07(19) . . . . ? C30 C26 C27 C28 0.0(3) . . . . ? C25 C26 C27 C28 -179.4(2) . . . . ? C26 C27 C28 N5 -0.2(3) . . . . ? N5 C29 C30 C26 0.0(3) . . . . ? C27 C26 C30 C29 0.2(3) . . . . ? C25 C26 C30 C29 179.5(2) . . . . ? O9 C31 C32 C33 -178.68(19) . . . . ? C36 C31 C32 C33 0.4(3) . . . . ? C31 C32 C33 O7 179.5(2) . . . . ? C31 C32 C33 C34 -0.8(3) . . . . ? O7 C33 C34 C35 179.8(2) . . . . ? C32 C33 C34 C35 0.0(3) . . . . ? C33 C34 C35 O8 -178.2(2) . . . . ? C33 C34 C35 C36 1.2(3) . . . . ? O9 C31 C36 C35 179.77(19) . . . . ? C32 C31 C36 C35 0.7(3) . . . . ? O8 C35 C36 C31 177.8(2) . . . . ? C34 C35 C36 C31 -1.5(3) . . . . ? C12 C11 N1 O2 178.70(18) . . . . ? C12 C11 N1 C10 -0.7(3) . . . . ? C9 C10 N1 O2 -177.84(19) . . . . ? C9 C10 N1 C11 1.6(3) . . . . ? O1 C7 N2 N3 -0.1(2) . . . . ? C8 C7 N2 N3 179.1(2) . . . . ? O1 C6 N3 N2 -0.5(2) . . . . ? C3 C6 N3 N2 179.2(2) . . . . ? C7 N2 N3 C6 0.4(2) . . . . ? C4 C5 N4 O3 -177.5(2) . . . . ? C4 C5 N4 C1 0.6(4) . . . . ? C2 C1 N4 O3 176.7(2) . . . . ? C2 C1 N4 C5 -1.5(4) . . . . ? C27 C28 N5 O5 -178.8(2) . . . . ? C27 C28 N5 C29 0.4(3) . . . . ? C30 C29 N5 O5 178.9(2) . . . . ? C30 C29 N5 C28 -0.3(3) . . . . ? O4 C25 N6 N7 -0.2(2) . . . . ? C26 C25 N6 N7 179.8(2) . . . . ? O4 C24 N7 N6 0.0(2) . . . . ? C21 C24 N7 N6 -178.6(2) . . . . ? C25 N6 N7 C24 0.1(2) . . . . ? C20 C19 N8 O6 179.4(2) . . . . ? C20 C19 N8 C23 -0.6(3) . . . . ? C22 C23 N8 O6 -180.0(2) . . . . ? C22 C23 N8 C19 0.1(3) . . . . ? N3 C6 O1 C7 0.4(2) . . . . ? C3 C6 O1 C7 -179.29(18) . . . . ? N2 C7 O1 C6 -0.2(2) . . . . ? C8 C7 O1 C6 -179.48(17) . . . . ? N7 C24 O4 C25 -0.1(2) . . . . ? C21 C24 O4 C25 178.65(18) . . . . ? N6 C25 O4 C24 0.2(2) . . . . ? C26 C25 O4 C24 -179.79(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13A O9 0.88 1.94 2.814(2) 171.5 . O12 H12A O5 0.82 1.85 2.630(2) 159.8 2_645 O11 H11A O13 0.82 1.88 2.678(2) 164.6 . O10 H10A O3 0.82 1.79 2.604(3) 172.8 4_575 O9 H9A N1 0.82 2.60 3.326(2) 148.2 2_545 O9 H9A O2 0.82 1.84 2.656(2) 175.7 2_545 O8 H8 O11 0.82 2.09 2.895(3) 167.4 2_545 O7 H7 O6 0.82 1.84 2.657(3) 178.0 4_576 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.322 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.042 # Attachment '6.cif' #========================================================================== data_6 _database_code_depnum_ccdc_archive 'CCDC 735629' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N4 O6' _chemical_formula_sum 'C18 H16 N4 O6' _chemical_formula_weight 384.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 9.4118(18) _cell_length_b 7.0994(14) _cell_length_c 26.666(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.805(3) _cell_angle_gamma 90.00 _cell_volume 1772.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2145 _cell_measurement_theta_min 2.378 _cell_measurement_theta_max 23.043 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8961 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3308 _reflns_number_gt 2546 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0438P)^2^+0.5150P] 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_number_reflns 3308 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 1.2488(2) 0.6173(4) 0.04359(9) 0.0598(6) Uani 1 1 d . . . H1 H 1.3042 0.6035 0.0169 0.072 Uiso 1 1 calc R . . C2 C 1.1139(2) 0.6931(4) 0.03384(8) 0.0559(6) Uani 1 1 d . . . H2 H 1.0798 0.7302 0.0014 0.067 Uiso 1 1 calc R . . C3 C 1.0308(2) 0.7126(3) 0.07313(7) 0.0401(5) Uani 1 1 d . . . C4 C 1.0864(2) 0.6577(3) 0.12069(8) 0.0474(5) Uani 1 1 d . . . H4 H 1.0333 0.6699 0.1481 0.057 Uiso 1 1 calc R . . C5 C 1.2227(2) 0.5843(3) 0.12654(9) 0.0517(6) Uani 1 1 d . . . H5 H 1.2600 0.5475 0.1587 0.062 Uiso 1 1 calc R . . C6 C 0.8874(2) 0.7899(3) 0.06331(7) 0.0409(5) Uani 1 1 d . . . C7 C 0.68323(19) 0.8836(3) 0.07880(7) 0.0369(4) Uani 1 1 d . . . C8 C 0.56738(18) 0.9296(3) 0.10872(7) 0.0345(4) Uani 1 1 d . . . C9 C 0.44527(19) 1.0160(3) 0.08585(7) 0.0401(5) Uani 1 1 d . . . H9 H 0.4370 1.0411 0.0514 0.048 Uiso 1 1 calc R . . C10 C 0.3377(2) 1.0638(3) 0.11391(7) 0.0407(5) Uani 1 1 d . . . H10 H 0.2557 1.1212 0.0985 0.049 Uiso 1 1 calc R . . C11 C 0.4656(2) 0.9432(3) 0.18641(7) 0.0412(5) Uani 1 1 d . . . H11 H 0.4711 0.9187 0.2208 0.049 Uiso 1 1 calc R . . C12 C 0.5761(2) 0.8917(3) 0.15975(7) 0.0385(5) Uani 1 1 d . . . H12 H 0.6561 0.8320 0.1758 0.046 Uiso 1 1 calc R . . C13 C 0.66595(19) 0.3928(3) 0.11533(7) 0.0407(5) Uani 1 1 d . . . C14 C 0.6267(2) 0.3805(3) 0.16352(7) 0.0400(5) Uani 1 1 d . . . H14 H 0.5394 0.4281 0.1711 0.048 Uiso 1 1 calc R . . C15 C 0.7189(2) 0.2964(3) 0.20048(7) 0.0414(5) Uani 1 1 d . . . C16 C 0.8506(2) 0.2284(3) 0.18995(8) 0.0440(5) Uani 1 1 d . . . H16 H 0.9125 0.1729 0.2151 0.053 Uiso 1 1 calc R . . C17 C 0.8880(2) 0.2444(3) 0.14172(8) 0.0429(5) Uani 1 1 d . . . C18 C 0.7970(2) 0.3259(3) 0.10433(8) 0.0457(5) Uani 1 1 d . . . H18 H 0.8236 0.3360 0.0718 0.055 Uiso 1 1 calc R . . N1 N 0.82219(18) 0.8411(3) 0.02072(6) 0.0541(5) Uani 1 1 d . . . N2 N 0.68716(17) 0.9035(3) 0.03121(6) 0.0511(5) Uani 1 1 d . . . N3 N 1.30362(17) 0.5631(3) 0.08904(7) 0.0515(5) Uani 1 1 d . . . N4 N 0.34911(16) 1.0288(2) 0.16343(6) 0.0392(4) Uani 1 1 d . . . O1 O 0.80628(12) 0.81199(18) 0.10215(4) 0.0379(3) Uani 1 1 d . . . O2 O 0.24579(14) 1.0828(2) 0.19116(5) 0.0527(4) Uani 1 1 d . . . O3 O 0.58090(15) 0.4707(2) 0.07672(6) 0.0591(4) Uani 1 1 d . . . H3 H 0.4999 0.4834 0.0850 0.089 Uiso 1 1 calc R . . O4 O 1.01371(15) 0.1772(3) 0.12712(6) 0.0646(5) Uani 1 1 d . . . H4A H 1.0677 0.1499 0.1521 0.097 Uiso 1 1 calc R . . O5 O 0.68329(16) 0.2731(3) 0.24848(5) 0.0610(4) Uani 1 1 d . . . H5A H 0.5998 0.3041 0.2498 0.092 Uiso 1 1 calc R . . O6 O 0.10296(18) 0.8426(3) 0.24801(7) 0.0943(7) Uani 1 1 d . . . H6B H 0.1542 0.9073 0.2264 0.142 Uiso 1 1 d R . . H6A H 0.1707 0.7746 0.2655 0.142 Uiso 1 1 d 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 C1 0.0399(13) 0.0834(18) 0.0572(14) -0.0053(12) 0.0101(11) 0.0165(12) C2 0.0387(12) 0.0833(17) 0.0460(12) -0.0016(11) 0.0050(9) 0.0193(12) C3 0.0316(10) 0.0417(11) 0.0468(11) -0.0034(9) 0.0030(8) 0.0048(9) C4 0.0378(11) 0.0565(13) 0.0484(12) 0.0025(10) 0.0063(9) 0.0058(10) C5 0.0402(12) 0.0572(14) 0.0561(13) 0.0075(11) -0.0023(10) 0.0069(10) C6 0.0335(11) 0.0486(12) 0.0412(11) -0.0029(9) 0.0068(9) 0.0065(9) C7 0.0300(10) 0.0413(11) 0.0383(11) -0.0003(8) -0.0029(8) 0.0064(8) C8 0.0292(10) 0.0349(10) 0.0390(10) -0.0029(8) 0.0010(8) 0.0015(8) C9 0.0343(10) 0.0497(12) 0.0354(10) 0.0031(9) -0.0003(8) 0.0069(9) C10 0.0289(10) 0.0474(12) 0.0449(12) 0.0039(9) -0.0009(8) 0.0069(9) C11 0.0366(11) 0.0471(12) 0.0392(11) 0.0049(9) 0.0009(8) 0.0036(9) C12 0.0296(10) 0.0427(11) 0.0421(11) 0.0015(9) -0.0017(8) 0.0065(8) C13 0.0302(10) 0.0424(12) 0.0496(12) 0.0045(9) 0.0038(9) 0.0038(8) C14 0.0287(10) 0.0396(11) 0.0522(12) -0.0062(9) 0.0069(9) 0.0048(8) C15 0.0379(11) 0.0460(12) 0.0399(11) -0.0066(9) 0.0019(8) -0.0033(9) C16 0.0319(11) 0.0492(12) 0.0491(12) -0.0024(9) -0.0047(9) 0.0044(9) C17 0.0254(10) 0.0455(12) 0.0584(13) -0.0042(9) 0.0069(9) 0.0031(8) C18 0.0343(11) 0.0576(13) 0.0467(12) 0.0042(10) 0.0114(9) 0.0054(10) N1 0.0392(10) 0.0806(14) 0.0430(10) 0.0025(9) 0.0068(8) 0.0200(9) N2 0.0378(10) 0.0742(13) 0.0410(10) 0.0020(8) 0.0027(8) 0.0188(9) N3 0.0342(9) 0.0534(11) 0.0661(12) -0.0005(9) 0.0017(9) 0.0092(8) N4 0.0290(8) 0.0427(9) 0.0467(10) 0.0005(7) 0.0073(7) 0.0023(7) O1 0.0286(7) 0.0456(8) 0.0391(7) -0.0004(6) 0.0020(6) 0.0077(6) O2 0.0353(8) 0.0673(10) 0.0582(9) 0.0012(7) 0.0189(7) 0.0091(7) O3 0.0386(8) 0.0798(11) 0.0593(9) 0.0215(8) 0.0068(7) 0.0176(8) O4 0.0347(8) 0.0868(12) 0.0734(11) 0.0035(10) 0.0111(7) 0.0207(8) O5 0.0514(9) 0.0896(12) 0.0417(8) -0.0072(8) 0.0029(7) 0.0074(9) O6 0.0506(10) 0.1417(18) 0.0942(14) 0.0591(13) 0.0247(10) 0.0077(11) _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 N3 1.325(3) . ? C1 C2 1.379(3) . ? C1 H1 0.9300 . ? C2 C3 1.377(3) . ? C2 H2 0.9300 . ? C3 C4 1.378(3) . ? C3 C6 1.456(3) . ? C4 C5 1.379(3) . ? C4 H4 0.9300 . ? C5 N3 1.325(3) . ? C5 H5 0.9300 . ? C6 N1 1.287(2) . ? C6 O1 1.356(2) . ? C7 N2 1.281(2) . ? C7 O1 1.357(2) . ? C7 C8 1.452(3) . ? C8 C12 1.381(3) . ? C8 C9 1.388(3) . ? C9 C10 1.362(3) . ? C9 H9 0.9300 . ? C10 N4 1.337(2) . ? C10 H10 0.9300 . ? C11 N4 1.346(2) . ? C11 C12 1.367(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O3 1.357(2) . ? C13 C14 1.375(3) . ? C13 C18 1.380(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 O5 1.365(2) . ? C15 C16 1.386(3) . ? C16 C17 1.372(3) . ? C16 H16 0.9300 . ? C17 O4 1.368(2) . ? C17 C18 1.375(3) . ? C18 H18 0.9300 . ? N1 N2 1.401(2) . ? N4 O2 1.3358(19) . ? O3 H3 0.8200 . ? O4 H4A 0.8200 . ? O5 H5A 0.8200 . ? O6 H6B 0.9115 . ? O6 H6A 0.8929 . ? 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 N3 C1 C2 123.5(2) . . ? N3 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 118.66(18) . . ? C2 C3 C6 119.28(18) . . ? C4 C3 C6 122.05(18) . . ? C3 C4 C5 118.25(19) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N3 C5 C4 123.8(2) . . ? N3 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? N1 C6 O1 112.72(16) . . ? N1 C6 C3 127.98(18) . . ? O1 C6 C3 119.30(16) . . ? N2 C7 O1 112.76(16) . . ? N2 C7 C8 128.17(17) . . ? O1 C7 C8 119.06(16) . . ? C12 C8 C9 118.87(17) . . ? C12 C8 C7 121.63(16) . . ? C9 C8 C7 119.50(17) . . ? C10 C9 C8 119.83(18) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N4 C10 C9 120.42(17) . . ? N4 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? N4 C11 C12 120.75(18) . . ? N4 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C8 119.20(17) . . ? C11 C12 H12 120.4 . . ? C8 C12 H12 120.4 . . ? O3 C13 C14 122.79(17) . . ? O3 C13 C18 116.75(18) . . ? C14 C13 C18 120.46(18) . . ? C13 C14 C15 119.06(17) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? O5 C15 C14 121.71(18) . . ? O5 C15 C16 117.19(18) . . ? C14 C15 C16 121.08(18) . . ? C17 C16 C15 118.75(18) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? O4 C17 C16 123.32(19) . . ? O4 C17 C18 115.70(18) . . ? C16 C17 C18 120.96(18) . . ? C17 C18 C13 119.67(19) . . ? C17 C18 H18 120.2 . . ? C13 C18 H18 120.2 . . ? C6 N1 N2 105.91(16) . . ? C7 N2 N1 106.30(15) . . ? C5 N3 C1 117.15(18) . . ? O2 N4 C10 120.18(15) . . ? O2 N4 C11 118.87(16) . . ? C10 N4 C11 120.93(16) . . ? C6 O1 C7 102.31(14) . . ? C13 O3 H3 109.5 . . ? C17 O4 H4A 109.5 . . ? C15 O5 H5A 109.5 . . ? H6B O6 H6A 102.0 . . ? 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 N3 C1 C2 C3 -0.5(4) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C1 C2 C3 C6 -179.1(2) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C6 C3 C4 C5 179.4(2) . . . . ? C3 C4 C5 N3 -0.1(3) . . . . ? C2 C3 C6 N1 2.0(3) . . . . ? C4 C3 C6 N1 -177.9(2) . . . . ? C2 C3 C6 O1 -178.97(19) . . . . ? C4 C3 C6 O1 1.2(3) . . . . ? N2 C7 C8 C12 176.9(2) . . . . ? O1 C7 C8 C12 -4.0(3) . . . . ? N2 C7 C8 C9 -4.0(3) . . . . ? O1 C7 C8 C9 175.18(17) . . . . ? C12 C8 C9 C10 0.8(3) . . . . ? C7 C8 C9 C10 -178.37(18) . . . . ? C8 C9 C10 N4 0.3(3) . . . . ? N4 C11 C12 C8 0.4(3) . . . . ? C9 C8 C12 C11 -1.1(3) . . . . ? C7 C8 C12 C11 178.05(18) . . . . ? O3 C13 C14 C15 179.03(19) . . . . ? C18 C13 C14 C15 -1.5(3) . . . . ? C13 C14 C15 O5 -177.22(18) . . . . ? C13 C14 C15 C16 1.4(3) . . . . ? O5 C15 C16 C17 178.07(19) . . . . ? C14 C15 C16 C17 -0.6(3) . . . . ? C15 C16 C17 O4 -178.17(19) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? O4 C17 C18 C13 178.19(19) . . . . ? C16 C17 C18 C13 0.0(3) . . . . ? O3 C13 C18 C17 -179.66(19) . . . . ? C14 C13 C18 C17 0.8(3) . . . . ? O1 C6 N1 N2 0.3(2) . . . . ? C3 C6 N1 N2 179.5(2) . . . . ? O1 C7 N2 N1 0.1(2) . . . . ? C8 C7 N2 N1 179.32(19) . . . . ? C6 N1 N2 C7 -0.3(2) . . . . ? C4 C5 N3 C1 0.3(3) . . . . ? C2 C1 N3 C5 0.0(4) . . . . ? C9 C10 N4 O2 177.31(17) . . . . ? C9 C10 N4 C11 -1.1(3) . . . . ? C12 C11 N4 O2 -177.65(17) . . . . ? C12 C11 N4 C10 0.8(3) . . . . ? N1 C6 O1 C7 -0.2(2) . . . . ? C3 C6 O1 C7 -179.45(17) . . . . ? N2 C7 O1 C6 0.0(2) . . . . ? C8 C7 O1 C6 -179.22(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6A N4 0.89 2.60 3.244(2) 130.2 2_545 O6 H6A O2 0.89 1.90 2.755(2) 159.0 2_545 O5 H5A O6 0.82 1.93 2.750(2) 172.5 2_545 O4 H4A O2 0.82 1.94 2.717(2) 157.6 1_645 O3 H3 N3 0.82 1.95 2.743(2) 163.9 1_455 O6 H6B O2 0.91 1.83 2.725(2) 167.2 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.190 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.037 # Attachment '7.cif' #========================================================================== data_7 _database_code_depnum_ccdc_archive 'CCDC 735630' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C72 H58 N16 O21' _chemical_formula_sum 'C72 H58 N16 O21' _chemical_formula_weight 1483.34 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.002(4) _cell_length_b 7.804(3) _cell_length_c 35.338(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.773(6) _cell_angle_gamma 90.00 _cell_volume 3305.7(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8428 _diffrn_reflns_av_R_equivalents 0.0640 _diffrn_reflns_av_sigmaI/netI 0.1142 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3062 _reflns_number_gt 1563 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3062 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1401 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1649 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 N4 N 0.6416(2) 1.0312(4) 0.71859(8) 0.0537(8) Uani 1 1 d . . . O1 O 0.52169(18) 0.8736(3) 0.58620(7) 0.0540(6) Uani 1 1 d . . . O2 O 0.7577(2) 0.8158(3) 0.88384(7) 0.0702(8) Uani 1 1 d . . . C8 C 0.6182(3) 0.8902(4) 0.64755(10) 0.0475(9) Uani 1 1 d . . . O5 O 0.6528(2) 1.0991(3) 0.75272(7) 0.0694(8) Uani 1 1 d . . . C16 C 0.6267(3) 0.5935(4) 0.87118(10) 0.0541(9) Uani 1 1 d . . . O4 O 0.7304(2) 0.9277(3) 0.81183(7) 0.0666(7) Uani 1 1 d . . . H4 H 0.7027 0.9715 0.7925 0.100 Uiso 1 1 calc R . . C14 C 0.6686(3) 0.7887(4) 0.82132(10) 0.0519(9) Uani 1 1 d . . . C12 C 0.5517(3) 1.0250(4) 0.65807(10) 0.0546(10) Uani 1 1 d . . . H12 H 0.4978 1.0690 0.6410 0.065 Uiso 1 1 calc R . . O3 O 0.6412(2) 0.5362(3) 0.90756(7) 0.0714(8) Uani 1 1 d . . . H3 H 0.7012 0.5707 0.9167 0.107 Uiso 1 1 calc R . . N3 N 0.3159(3) 0.8799(4) 0.45877(9) 0.0627(8) Uani 1 1 d . . . C11 C 0.5650(3) 1.0936(4) 0.69354(10) 0.0564(10) Uani 1 1 d . . . H11 H 0.5203 1.1849 0.7003 0.068 Uiso 1 1 calc R . . C7 C 0.6035(3) 0.8122(5) 0.61012(10) 0.0522(9) Uani 1 1 d . . . C10 C 0.7083(3) 0.9006(4) 0.70905(10) 0.0545(9) Uani 1 1 d . . . H10 H 0.7621 0.8592 0.7265 0.065 Uiso 1 1 calc R . . C9 C 0.6972(3) 0.8288(4) 0.67375(10) 0.0537(9) Uani 1 1 d . . . H9 H 0.7431 0.7383 0.6674 0.064 Uiso 1 1 calc R . . C13 C 0.5927(3) 0.7063(5) 0.79688(10) 0.0585(10) Uani 1 1 d . . . H13 H 0.5821 0.7432 0.7719 0.070 Uiso 1 1 calc R . . C15 C 0.6853(3) 0.7347(4) 0.85848(10) 0.0497(9) Uani 1 1 d . . . C2 C 0.4718(3) 0.7301(5) 0.48782(11) 0.0619(10) Uani 1 1 d . . . H2A H 0.5297 0.6525 0.4851 0.074 Uiso 1 1 calc R . . C3 C 0.4567(3) 0.8076(4) 0.52215(10) 0.0541(9) Uani 1 1 d . . . N2 N 0.6111(3) 0.6653(4) 0.55901(9) 0.0670(9) Uani 1 1 d . . . C17 C 0.5497(3) 0.5131(4) 0.84660(12) 0.0592(10) Uani 1 1 d . . . H17 H 0.5091 0.4203 0.8550 0.071 Uiso 1 1 calc R . . C6 C 0.5309(3) 0.7752(5) 0.55471(10) 0.0558(9) Uani 1 1 d . . . C1 C 0.3998(3) 0.7691(5) 0.45743(11) 0.0648(10) Uani 1 1 d . . . H1 H 0.4106 0.7144 0.4345 0.078 Uiso 1 1 calc R . . C4 C 0.3681(3) 0.9220(5) 0.52441(11) 0.0621(10) Uani 1 1 d . . . H4A H 0.3540 0.9761 0.5471 0.075 Uiso 1 1 calc R . . C18 C 0.5328(3) 0.5693(5) 0.80973(11) 0.0610(10) Uani 1 1 d . . . H18 H 0.4807 0.5146 0.7935 0.073 Uiso 1 1 calc R . . N1 N 0.6589(3) 0.6882(4) 0.59582(9) 0.0646(9) Uani 1 1 d . . . C5 C 0.3018(3) 0.9534(5) 0.49227(11) 0.0640(10) Uani 1 1 d . . . H5 H 0.2434 1.0309 0.4940 0.077 Uiso 1 1 calc R . . H2 H 0.7701 0.8998 0.8706 0.077 Uiso 1 1 d R . . O6 O 0.3782(16) 0.195(3) 0.5898(7) 0.227(10) Uani 0.25 1 d P . . H1O6 H 0.3844 0.3026 0.5880 0.341 Uiso 0.25 1 d PR . . H2O6 H 0.3194 0.1740 0.6015 0.341 Uiso 0.25 1 d PR . . 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 N4 0.0649(19) 0.0526(19) 0.042(2) 0.0018(15) -0.0114(16) -0.0080(15) O1 0.0645(15) 0.0539(15) 0.0423(15) 0.0061(11) -0.0094(13) -0.0184(11) O2 0.0880(18) 0.0662(17) 0.0533(17) 0.0026(12) -0.0273(15) -0.0078(13) C8 0.051(2) 0.044(2) 0.047(2) 0.0036(16) -0.0043(18) -0.0109(16) O5 0.093(2) 0.0696(17) 0.0434(17) -0.0042(12) -0.0167(14) -0.0024(13) C16 0.063(2) 0.055(2) 0.044(2) -0.0061(18) -0.0042(19) 0.0150(19) O4 0.0764(17) 0.0672(17) 0.0538(18) 0.0054(13) -0.0209(14) -0.0128(14) C14 0.050(2) 0.055(2) 0.049(2) -0.0048(18) -0.0080(19) 0.0022(18) C12 0.059(2) 0.055(2) 0.048(3) 0.0098(18) -0.0181(19) -0.0111(18) O3 0.089(2) 0.0712(18) 0.0535(18) 0.0038(13) -0.0045(15) -0.0005(14) N3 0.069(2) 0.065(2) 0.053(2) 0.0071(16) -0.0076(18) -0.0226(17) C11 0.061(2) 0.054(2) 0.053(3) 0.0071(18) -0.016(2) -0.0005(18) C7 0.055(2) 0.055(2) 0.046(2) 0.0064(18) -0.007(2) -0.0104(18) C10 0.062(2) 0.051(2) 0.049(2) 0.0093(17) -0.0131(19) -0.0007(18) C9 0.059(2) 0.051(2) 0.050(2) 0.0030(18) -0.008(2) 0.0017(17) C13 0.060(2) 0.067(3) 0.047(2) -0.0082(19) -0.016(2) 0.004(2) C15 0.053(2) 0.050(2) 0.044(2) -0.0074(17) -0.0142(18) 0.0104(17) C2 0.071(2) 0.068(2) 0.046(3) 0.0008(19) -0.009(2) -0.0179(19) C3 0.066(2) 0.055(2) 0.040(2) 0.0052(17) -0.008(2) -0.0236(19) N2 0.078(2) 0.069(2) 0.053(2) -0.0061(16) -0.0075(18) -0.0095(18) C17 0.059(2) 0.049(2) 0.069(3) -0.0097(19) -0.002(2) 0.0022(17) C6 0.069(3) 0.057(2) 0.041(2) 0.0013(18) -0.001(2) -0.017(2) C1 0.079(3) 0.071(3) 0.044(3) -0.0008(19) -0.006(2) -0.023(2) C4 0.068(2) 0.068(3) 0.049(3) 0.0049(19) -0.002(2) -0.025(2) C18 0.057(2) 0.063(3) 0.061(3) -0.014(2) -0.015(2) 0.0022(19) N1 0.077(2) 0.065(2) 0.050(2) -0.0067(16) -0.0115(18) -0.0046(17) C5 0.067(2) 0.071(3) 0.053(3) 0.004(2) -0.007(2) -0.019(2) O6 0.20(2) 0.25(2) 0.23(3) -0.049(18) 0.015(18) 0.046(17) _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 N4 O5 1.318(3) . ? N4 C11 1.337(4) . ? N4 C10 1.348(4) . ? O1 C7 1.352(4) . ? O1 C6 1.361(4) . ? O2 C15 1.372(4) . ? O2 H2 0.8230 . ? C8 C9 1.378(4) . ? C8 C12 1.382(4) . ? C8 C7 1.459(5) . ? C16 O3 1.364(4) . ? C16 C17 1.387(5) . ? C16 C15 1.393(5) . ? O4 C14 1.365(4) . ? O4 H4 0.8200 . ? C14 C13 1.383(4) . ? C14 C15 1.384(5) . ? C12 C11 1.365(5) . ? C12 H12 0.9300 . ? O3 H3 0.8200 . ? N3 C1 1.330(4) . ? N3 C5 1.334(4) . ? C11 H11 0.9300 . ? C7 N1 1.291(4) . ? C10 C9 1.368(5) . ? C10 H10 0.9300 . ? C9 H9 0.9300 . ? C13 C18 1.377(5) . ? C13 H13 0.9300 . ? C2 C3 1.376(5) . ? C2 C1 1.379(5) . ? C2 H2A 0.9300 . ? C3 C4 1.394(5) . ? C3 C6 1.443(5) . ? N2 C6 1.293(4) . ? N2 N1 1.407(4) . ? C17 C18 1.381(5) . ? C17 H17 0.9300 . ? C1 H1 0.9300 . ? C4 C5 1.376(5) . ? C4 H4A 0.9300 . ? C18 H18 0.9300 . ? C5 H5 0.9300 . ? O6 H1O6 0.8500 . ? O6 H2O6 0.8500 . ? 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 O5 N4 C11 119.7(3) . . ? O5 N4 C10 119.8(3) . . ? C11 N4 C10 120.5(3) . . ? C7 O1 C6 103.1(3) . . ? C15 O2 H2 97.1 . . ? C9 C8 C12 118.1(3) . . ? C9 C8 C7 120.9(3) . . ? C12 C8 C7 121.0(3) . . ? O3 C16 C17 119.5(4) . . ? O3 C16 C15 121.3(3) . . ? C17 C16 C15 119.2(3) . . ? C14 O4 H4 109.5 . . ? O4 C14 C13 124.4(3) . . ? O4 C14 C15 114.8(3) . . ? C13 C14 C15 120.8(4) . . ? C11 C12 C8 120.2(3) . . ? C11 C12 H12 119.9 . . ? C8 C12 H12 119.9 . . ? C16 O3 H3 109.5 . . ? C1 N3 C5 116.1(3) . . ? N4 C11 C12 120.7(3) . . ? N4 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? N1 C7 O1 113.1(3) . . ? N1 C7 C8 128.8(3) . . ? O1 C7 C8 118.1(3) . . ? N4 C10 C9 120.3(3) . . ? N4 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C18 C13 C14 119.6(4) . . ? C18 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? O2 C15 C14 122.5(3) . . ? O2 C15 C16 117.9(3) . . ? C14 C15 C16 119.6(3) . . ? C3 C2 C1 119.0(4) . . ? C3 C2 H2A 120.5 . . ? C1 C2 H2A 120.5 . . ? C2 C3 C4 117.7(4) . . ? C2 C3 C6 121.6(4) . . ? C4 C3 C6 120.7(3) . . ? C6 N2 N1 107.0(3) . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? N2 C6 O1 111.6(3) . . ? N2 C6 C3 129.6(4) . . ? O1 C6 C3 118.8(4) . . ? N3 C1 C2 124.3(4) . . ? N3 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C5 C4 C3 118.6(4) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C13 C18 C17 120.1(3) . . ? C13 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C7 N1 N2 105.2(3) . . ? N3 C5 C4 124.3(4) . . ? N3 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? H1O6 O6 H2O6 107.7 . . ? 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 C9 C8 C12 C11 -0.1(5) . . . . ? C7 C8 C12 C11 178.5(3) . . . . ? O5 N4 C11 C12 -179.8(3) . . . . ? C10 N4 C11 C12 1.0(5) . . . . ? C8 C12 C11 N4 -0.5(5) . . . . ? C6 O1 C7 N1 -0.2(4) . . . . ? C6 O1 C7 C8 179.9(3) . . . . ? C9 C8 C7 N1 -2.5(6) . . . . ? C12 C8 C7 N1 179.0(4) . . . . ? C9 C8 C7 O1 177.4(3) . . . . ? C12 C8 C7 O1 -1.1(5) . . . . ? O5 N4 C10 C9 179.8(3) . . . . ? C11 N4 C10 C9 -1.0(5) . . . . ? N4 C10 C9 C8 0.4(5) . . . . ? C12 C8 C9 C10 0.1(5) . . . . ? C7 C8 C9 C10 -178.5(3) . . . . ? O4 C14 C13 C18 -178.5(3) . . . . ? C15 C14 C13 C18 0.2(5) . . . . ? O4 C14 C15 O2 0.6(5) . . . . ? C13 C14 C15 O2 -178.3(3) . . . . ? O4 C14 C15 C16 -179.8(3) . . . . ? C13 C14 C15 C16 1.4(5) . . . . ? O3 C16 C15 O2 -0.5(5) . . . . ? C17 C16 C15 O2 177.5(3) . . . . ? O3 C16 C15 C14 179.8(3) . . . . ? C17 C16 C15 C14 -2.2(5) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C1 C2 C3 C6 -178.5(3) . . . . ? O3 C16 C17 C18 179.5(3) . . . . ? C15 C16 C17 C18 1.4(5) . . . . ? N1 N2 C6 O1 0.8(4) . . . . ? N1 N2 C6 C3 178.8(3) . . . . ? C7 O1 C6 N2 -0.4(4) . . . . ? C7 O1 C6 C3 -178.6(3) . . . . ? C2 C3 C6 N2 -7.3(6) . . . . ? C4 C3 C6 N2 174.0(4) . . . . ? C2 C3 C6 O1 170.6(3) . . . . ? C4 C3 C6 O1 -8.2(5) . . . . ? C5 N3 C1 C2 -1.2(5) . . . . ? C3 C2 C1 N3 0.8(5) . . . . ? C2 C3 C4 C5 -1.0(5) . . . . ? C6 C3 C4 C5 177.8(3) . . . . ? C14 C13 C18 C17 -1.0(5) . . . . ? C16 C17 C18 C13 0.2(5) . . . . ? O1 C7 N1 N2 0.6(4) . . . . ? C8 C7 N1 N2 -179.5(3) . . . . ? C6 N2 N1 C7 -0.8(4) . . . . ? C1 N3 C5 C4 0.4(5) . . . . ? C3 C4 C5 N3 0.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H2O6 N1 0.85 1.93 2.650(19) 141.8 3_445 O6 H1O6 O3 0.85 1.86 2.68(2) 162.2 2_656 O2 H2 N1 0.82 2.66 3.146(4) 118.9 4_656 O2 H2 O4 0.82 2.12 2.695(3) 126.8 . O3 H3 N3 0.82 2.01 2.781(4) 155.5 8_566 O4 H4 O5 0.82 1.80 2.614(3) 170.7 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.166 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.041 # Attachment '8.cif' #========================================================================== data_8 _database_code_depnum_ccdc_archive 'CCDC 735631' #TrackingRef '8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 N4 O7' _chemical_formula_sum 'C19 H14 N4 O7' _chemical_formula_weight 410.34 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.351(3) _cell_length_b 6.9394(18) _cell_length_c 13.099(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.018(4) _cell_angle_gamma 90.00 _cell_volume 894.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1448 _cell_measurement_theta_min 3.009 _cell_measurement_theta_max 25.519 _exptl_crystal_description bar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4731 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3097 _reflns_number_gt 2670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0259P)^2^+0.1481P] 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 2.1(2) _refine_ls_number_reflns 3097 _refine_ls_number_parameters 275 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.6802(3) -0.0128(6) 0.6231(3) 0.0663(10) Uani 1 1 d . . . H1 H 0.7168 -0.0362 0.5677 0.080 Uiso 1 1 calc R . . C2 C 0.5468(3) 0.0438(5) 0.5968(2) 0.0567(9) Uani 1 1 d . . . H2A H 0.4944 0.0553 0.5252 0.068 Uiso 1 1 calc R . . C3 C 0.4919(2) 0.0833(4) 0.6772(2) 0.0392(6) Uani 1 1 d . . . C4 C 0.5735(3) 0.0670(4) 0.7818(2) 0.0432(7) Uani 1 1 d . . . H4A H 0.5407 0.0963 0.8385 0.052 Uiso 1 1 calc R . . C5 C 0.7059(3) 0.0058(5) 0.8004(2) 0.0529(8) Uani 1 1 d . . . H5A H 0.7606 -0.0068 0.8712 0.063 Uiso 1 1 calc R . . C6 C 0.3501(2) 0.1413(4) 0.65158(19) 0.0351(6) Uani 1 1 d . . . C7 C 0.1690(2) 0.2326(4) 0.67924(19) 0.0329(6) Uani 1 1 d . . . C8 C 0.0817(2) 0.2954(4) 0.74113(19) 0.0320(6) Uani 1 1 d . . . C9 C -0.0473(2) 0.3658(4) 0.6898(2) 0.0384(7) Uani 1 1 d . . . H9 H -0.0789 0.3727 0.6153 0.046 Uiso 1 1 calc R . . C10 C -0.1280(2) 0.4250(4) 0.7489(2) 0.0403(7) Uani 1 1 d . . . H10 H -0.2141 0.4740 0.7145 0.048 Uiso 1 1 calc R . . C11 C 0.0409(2) 0.3446(4) 0.90772(19) 0.0399(7) Uani 1 1 d . . . H11 H 0.0698 0.3365 0.9822 0.048 Uiso 1 1 calc R . . C12 C 0.1254(2) 0.2871(4) 0.8515(2) 0.0359(6) Uani 1 1 d . . . H12 H 0.2123 0.2425 0.8878 0.043 Uiso 1 1 calc R . . C13 C 0.1848(2) 0.7162(4) 0.66375(18) 0.0331(6) Uani 1 1 d . . . C14 C 0.1035(2) 0.7827(4) 0.72354(19) 0.0304(6) Uani 1 1 d . . . C15 C 0.1573(2) 0.7957(4) 0.83407(19) 0.0342(6) Uani 1 1 d . . . C16 C 0.2915(2) 0.7485(4) 0.8846(2) 0.0370(7) Uani 1 1 d . . . H16 H 0.3277 0.7601 0.9587 0.044 Uiso 1 1 calc R . . C17 C 0.3726(2) 0.6838(4) 0.82454(19) 0.0343(6) Uani 1 1 d . . . C18 C 0.3179(2) 0.6674(4) 0.71396(19) 0.0343(6) Uani 1 1 d . . . H18 H 0.3716 0.6230 0.6736 0.041 Uiso 1 1 calc R . . C19 C 0.5163(3) 0.6339(4) 0.8809(2) 0.0403(7) Uani 1 1 d . . . N1 N 0.2603(2) 0.1515(4) 0.55886(16) 0.0445(6) Uani 1 1 d . . . N2 N 0.1410(2) 0.2133(4) 0.57750(16) 0.0411(6) Uani 1 1 d . . . N3 N 0.7596(2) -0.0359(4) 0.7234(2) 0.0574(7) Uani 1 1 d . . . N4 N -0.0837(2) 0.4128(3) 0.85627(16) 0.0370(5) Uani 1 1 d . . . O1 O 0.30055(15) 0.1903(3) 0.73261(12) 0.0344(4) Uani 1 1 d . . . O2 O -0.16323(17) 0.4706(3) 0.91242(14) 0.0540(6) Uani 1 1 d . . . O3 O 0.13296(16) 0.6968(3) 0.55561(12) 0.0475(5) Uani 1 1 d . . . H3 H 0.0520 0.7245 0.5364 0.071 Uiso 1 1 calc R . . O4 O -0.02563(16) 0.8281(3) 0.66883(14) 0.0451(5) Uani 1 1 d . . . H4 H -0.0659 0.8603 0.7111 0.068 Uiso 1 1 calc R . . O5 O 0.06802(17) 0.8522(3) 0.88608(15) 0.0495(6) Uani 1 1 d . . . H5 H 0.1102 0.8878 0.9470 0.074 Uiso 1 1 calc R . . O6 O 0.57720(18) 0.5546(4) 0.81637(15) 0.0573(6) Uani 1 1 d . . . H6 H 0.6571 0.5341 0.8498 0.086 Uiso 1 1 calc R . . O7 O 0.57253(18) 0.6649(4) 0.97408(15) 0.0635(6) 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 0.0452(17) 0.097(3) 0.061(2) -0.014(2) 0.0233(16) 0.0152(19) C2 0.0362(15) 0.087(3) 0.0463(17) -0.0073(17) 0.0119(13) 0.0148(17) C3 0.0299(13) 0.0406(17) 0.0474(16) 0.0004(13) 0.0123(11) 0.0017(12) C4 0.0355(14) 0.0530(19) 0.0427(15) -0.0015(14) 0.0143(12) 0.0007(13) C5 0.0324(14) 0.069(2) 0.0510(17) 0.0049(16) 0.0043(12) 0.0066(15) C6 0.0306(13) 0.0403(17) 0.0369(14) 0.0002(12) 0.0141(11) 0.0013(12) C7 0.0248(12) 0.0389(17) 0.0330(13) 0.0017(12) 0.0061(10) 0.0006(11) C8 0.0271(12) 0.0345(16) 0.0343(13) 0.0032(12) 0.0095(10) -0.0021(11) C9 0.0315(13) 0.0512(19) 0.0314(14) 0.0039(13) 0.0083(11) 0.0025(12) C10 0.0264(13) 0.0574(19) 0.0341(14) 0.0056(13) 0.0049(11) 0.0066(13) C11 0.0281(13) 0.058(2) 0.0292(14) 0.0044(13) 0.0028(11) 0.0063(13) C12 0.0231(12) 0.0474(17) 0.0356(14) 0.0031(12) 0.0067(11) 0.0045(12) C13 0.0280(12) 0.0406(16) 0.0300(13) -0.0001(12) 0.0080(10) -0.0043(12) C14 0.0224(11) 0.0316(15) 0.0356(14) 0.0013(11) 0.0067(10) -0.0017(10) C15 0.0321(13) 0.0368(16) 0.0383(15) -0.0033(12) 0.0176(11) -0.0047(12) C16 0.0337(13) 0.0456(19) 0.0289(13) 0.0018(12) 0.0056(11) -0.0023(12) C17 0.0249(12) 0.0367(16) 0.0385(14) -0.0020(12) 0.0055(10) -0.0007(12) C18 0.0283(12) 0.0382(16) 0.0381(14) -0.0001(13) 0.0130(11) 0.0015(12) C19 0.0315(13) 0.0433(19) 0.0409(15) 0.0007(13) 0.0035(12) 0.0029(12) N1 0.0326(11) 0.0653(18) 0.0377(12) 0.0038(12) 0.0139(10) 0.0086(11) N2 0.0299(11) 0.0591(16) 0.0358(12) 0.0049(12) 0.0121(9) 0.0084(11) N3 0.0337(12) 0.071(2) 0.0674(17) -0.0011(15) 0.0148(12) 0.0108(13) N4 0.0271(11) 0.0522(15) 0.0336(12) 0.0005(10) 0.0120(9) 0.0029(10) O1 0.0260(8) 0.0432(11) 0.0340(9) 0.0006(9) 0.0092(7) 0.0043(8) O2 0.0335(10) 0.0925(17) 0.0405(10) 0.0014(11) 0.0180(8) 0.0171(11) O3 0.0315(9) 0.0778(15) 0.0304(9) -0.0071(10) 0.0054(7) 0.0032(11) O4 0.0263(9) 0.0654(14) 0.0415(11) 0.0014(10) 0.0073(8) 0.0087(9) O5 0.0373(10) 0.0743(16) 0.0417(11) -0.0086(11) 0.0193(9) 0.0003(11) O6 0.0295(10) 0.0835(17) 0.0527(12) -0.0057(12) 0.0036(8) 0.0181(11) O7 0.0397(11) 0.0935(18) 0.0453(12) -0.0057(12) -0.0044(9) 0.0101(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 C1 N3 1.327(4) . ? C1 C2 1.373(4) . ? C1 H1 0.9300 . ? C2 C3 1.370(3) . ? C2 H2A 0.9300 . ? C3 C4 1.374(4) . ? C3 C6 1.457(3) . ? C4 C5 1.382(4) . ? C4 H4A 0.9300 . ? C5 N3 1.325(4) . ? C5 H5A 0.9300 . ? C6 N1 1.283(3) . ? C6 O1 1.357(3) . ? C7 N2 1.280(3) . ? C7 O1 1.357(3) . ? C7 C8 1.455(3) . ? C8 C12 1.377(3) . ? C8 C9 1.385(3) . ? C9 C10 1.366(3) . ? C9 H9 0.9300 . ? C10 N4 1.340(3) . ? C10 H10 0.9300 . ? C11 N4 1.343(3) . ? C11 C12 1.366(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O3 1.357(3) . ? C13 C18 1.373(3) . ? C13 C14 1.393(3) . ? C14 O4 1.344(3) . ? C14 C15 1.384(3) . ? C15 O5 1.365(3) . ? C15 C16 1.381(3) . ? C16 C17 1.390(3) . ? C16 H16 0.9300 . ? C17 C18 1.387(3) . ? C17 C19 1.482(3) . ? C18 H18 0.9300 . ? C19 O7 1.198(3) . ? C19 O6 1.321(3) . ? N1 N2 1.398(3) . ? N4 O2 1.325(2) . ? O3 H3 0.8200 . ? O4 H4 0.8200 . ? O5 H5 0.8200 . ? O6 H6 0.8200 . ? 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 N3 C1 C2 123.3(3) . . ? N3 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 119.2(3) . . ? C3 C2 H2A 120.4 . . ? C1 C2 H2A 120.4 . . ? C2 C3 C4 118.4(2) . . ? C2 C3 C6 120.4(2) . . ? C4 C3 C6 121.1(2) . . ? C3 C4 C5 118.1(2) . . ? C3 C4 H4A 121.0 . . ? C5 C4 H4A 121.0 . . ? N3 C5 C4 124.0(3) . . ? N3 C5 H5A 118.0 . . ? C4 C5 H5A 118.0 . . ? N1 C6 O1 112.8(2) . . ? N1 C6 C3 128.1(2) . . ? O1 C6 C3 119.1(2) . . ? N2 C7 O1 112.4(2) . . ? N2 C7 C8 129.2(2) . . ? O1 C7 C8 118.4(2) . . ? C12 C8 C9 118.6(2) . . ? C12 C8 C7 120.9(2) . . ? C9 C8 C7 120.4(2) . . ? C10 C9 C8 119.8(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? N4 C10 C9 120.3(2) . . ? N4 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? N4 C11 C12 120.6(2) . . ? N4 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C8 119.8(2) . . ? C11 C12 H12 120.1 . . ? C8 C12 H12 120.1 . . ? O3 C13 C18 119.3(2) . . ? O3 C13 C14 120.5(2) . . ? C18 C13 C14 120.2(2) . . ? O4 C14 C15 123.7(2) . . ? O4 C14 C13 116.9(2) . . ? C15 C14 C13 119.5(2) . . ? O5 C15 C16 124.4(2) . . ? O5 C15 C14 115.2(2) . . ? C16 C15 C14 120.3(2) . . ? C15 C16 C17 120.0(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C18 C17 C16 119.6(2) . . ? C18 C17 C19 121.5(2) . . ? C16 C17 C19 118.8(2) . . ? C13 C18 C17 120.3(2) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? O7 C19 O6 123.3(2) . . ? O7 C19 C17 124.2(2) . . ? O6 C19 C17 112.5(2) . . ? C6 N1 N2 105.79(19) . . ? C7 N2 N1 106.64(19) . . ? C5 N3 C1 116.8(2) . . ? O2 N4 C10 119.6(2) . . ? O2 N4 C11 119.6(2) . . ? C10 N4 C11 120.8(2) . . ? C7 O1 C6 102.31(18) . . ? C13 O3 H3 109.5 . . ? C14 O4 H4 109.5 . . ? C15 O5 H5 109.5 . . ? C19 O6 H6 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 C2 C3 1.5(6) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C1 C2 C3 C6 -179.2(3) . . . . ? C2 C3 C4 C5 -2.0(4) . . . . ? C6 C3 C4 C5 178.1(3) . . . . ? C3 C4 C5 N3 0.9(5) . . . . ? C2 C3 C6 N1 4.6(5) . . . . ? C4 C3 C6 N1 -175.5(3) . . . . ? C2 C3 C6 O1 -176.2(3) . . . . ? C4 C3 C6 O1 3.7(4) . . . . ? N2 C7 C8 C12 172.8(3) . . . . ? O1 C7 C8 C12 -8.8(4) . . . . ? N2 C7 C8 C9 -7.5(5) . . . . ? O1 C7 C8 C9 170.9(2) . . . . ? C12 C8 C9 C10 0.0(4) . . . . ? C7 C8 C9 C10 -179.8(3) . . . . ? C8 C9 C10 N4 -0.9(4) . . . . ? N4 C11 C12 C8 -1.3(4) . . . . ? C9 C8 C12 C11 1.1(4) . . . . ? C7 C8 C12 C11 -179.1(3) . . . . ? O3 C13 C14 O4 -1.0(4) . . . . ? C18 C13 C14 O4 179.9(3) . . . . ? O3 C13 C14 C15 178.0(2) . . . . ? C18 C13 C14 C15 -1.2(4) . . . . ? O4 C14 C15 O5 2.3(4) . . . . ? C13 C14 C15 O5 -176.6(2) . . . . ? O4 C14 C15 C16 -179.3(3) . . . . ? C13 C14 C15 C16 1.9(4) . . . . ? O5 C15 C16 C17 177.0(3) . . . . ? C14 C15 C16 C17 -1.4(4) . . . . ? C15 C16 C17 C18 0.1(4) . . . . ? C15 C16 C17 C19 -179.9(3) . . . . ? O3 C13 C18 C17 -179.2(3) . . . . ? C14 C13 C18 C17 0.0(4) . . . . ? C16 C17 C18 C13 0.5(4) . . . . ? C19 C17 C18 C13 -179.4(3) . . . . ? C18 C17 C19 O7 171.6(3) . . . . ? C16 C17 C19 O7 -8.3(4) . . . . ? C18 C17 C19 O6 -7.1(4) . . . . ? C16 C17 C19 O6 172.9(3) . . . . ? O1 C6 N1 N2 0.5(3) . . . . ? C3 C6 N1 N2 179.7(3) . . . . ? O1 C7 N2 N1 0.8(3) . . . . ? C8 C7 N2 N1 179.2(3) . . . . ? C6 N1 N2 C7 -0.8(3) . . . . ? C4 C5 N3 C1 1.4(5) . . . . ? C2 C1 N3 C5 -2.6(6) . . . . ? C9 C10 N4 O2 -179.9(3) . . . . ? C9 C10 N4 C11 0.8(4) . . . . ? C12 C11 N4 O2 -178.9(3) . . . . ? C12 C11 N4 C10 0.3(4) . . . . ? N2 C7 O1 C6 -0.4(3) . . . . ? C8 C7 O1 C6 -179.1(2) . . . . ? N1 C6 O1 C7 -0.1(3) . . . . ? C3 C6 O1 C7 -179.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 N2 0.82 2.09 2.835(2) 150.4 2_556 O3 H3 O4 0.82 2.24 2.689(2) 114.5 . O4 H4 N3 0.82 2.00 2.707(3) 144.5 1_465 O4 H4 O5 0.82 2.28 2.713(3) 113.2 . O5 H5 O2 0.82 1.84 2.647(3) 166.0 2_557 O5 H5 N4 0.82 2.68 3.355(3) 140.6 2_557 O6 H6 O2 0.82 1.84 2.655(2) 173.7 1_655 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.143 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.034 # Attachment 'A1.cif' #========================================================================== data_L1 _database_code_depnum_ccdc_archive 'CCDC 735632' #TrackingRef 'A1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N4 O3' _chemical_formula_sum 'C12 H8 N4 O3' _chemical_formula_weight 256.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 5.5420(17) _cell_length_b 12.465(4) _cell_length_c 16.069(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1110.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 311 _cell_measurement_theta_min 3.268 _cell_measurement_theta_max 18.216 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4892 _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1038 _reflns_number_gt 634 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0558P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1038 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 0.6953(5) 1.0077(2) 0.42568(16) 0.0417(7) Uani 1 1 d . . . H1 H 0.8063 1.0527 0.4514 0.050 Uiso 1 1 calc R . . C2 C 0.5117(5) 1.0505(2) 0.38046(15) 0.0376(7) Uani 1 1 d . . . H2 H 0.4984 1.1246 0.3756 0.045 Uiso 1 1 calc R . . C3 C 0.3430(4) 0.98435(18) 0.34127(15) 0.0330(7) Uani 1 1 d . . . C4 C 0.1516(5) 1.02901(18) 0.29127(15) 0.0341(7) Uani 1 1 d . . . C5 C 0.3682(5) 0.8749(2) 0.35158(17) 0.0415(7) Uani 1 1 d . . . H5 H 0.2580 0.8286 0.3268 0.050 Uiso 1 1 calc R . . C6 C 0.5540(5) 0.8338(2) 0.39802(16) 0.0474(8) Uani 1 1 d . . . H6 H 0.5669 0.7599 0.4051 0.057 Uiso 1 1 calc R . . N1 N 0.0994(4) 1.12810(15) 0.27676(13) 0.0422(6) Uani 1 1 d . . . N2 N 0.7182(4) 0.89912(18) 0.43359(14) 0.0445(6) Uani 1 1 d . . . O1 O 0.0000 0.96033(17) 0.2500 0.0349(7) Uani 1 2 d S . . O2 O 0.8947(4) 0.85867(16) 0.47622(13) 0.0675(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 C1 0.0428(19) 0.0407(17) 0.0416(18) 0.0008(14) -0.0023(15) -0.0079(13) C2 0.0422(16) 0.0316(14) 0.0389(17) -0.0011(12) 0.0004(14) -0.0047(13) C3 0.0338(16) 0.0315(15) 0.0336(15) -0.0016(12) 0.0015(13) -0.0001(12) C4 0.0400(17) 0.0285(15) 0.0339(16) -0.0031(12) 0.0029(13) -0.0047(13) C5 0.0409(17) 0.0334(15) 0.0503(18) 0.0004(14) -0.0088(15) -0.0029(13) C6 0.051(2) 0.0323(15) 0.059(2) 0.0016(14) -0.0059(16) 0.0000(14) N1 0.0484(16) 0.0288(12) 0.0495(15) 0.0015(10) -0.0100(11) 0.0006(10) N2 0.0386(14) 0.0464(15) 0.0486(15) 0.0059(12) -0.0045(13) -0.0023(12) O1 0.0402(15) 0.0259(13) 0.0387(16) 0.000 -0.0024(13) 0.000 O2 0.0531(14) 0.0681(15) 0.0812(16) 0.0147(12) -0.0284(12) 0.0041(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 C1 C2 1.360(3) . ? C1 N2 1.365(3) . ? C1 H1 0.9300 . ? C2 C3 1.397(3) . ? C2 H2 0.9300 . ? C3 C5 1.382(3) . ? C3 C4 1.442(3) . ? C4 N1 1.290(3) . ? C4 O1 1.371(3) . ? C5 C6 1.371(3) . ? C5 H5 0.9300 . ? C6 N2 1.349(3) . ? C6 H6 0.9300 . ? N1 N1 1.398(4) 3 ? N2 O2 1.296(3) . ? O1 C4 1.371(3) 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 C2 C1 N2 120.6(3) . . ? C2 C1 H1 119.7 . . ? N2 C1 H1 119.7 . . ? C1 C2 C3 120.6(2) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C5 C3 C2 117.5(2) . . ? C5 C3 C4 121.5(2) . . ? C2 C3 C4 121.0(2) . . ? N1 C4 O1 111.9(2) . . ? N1 C4 C3 129.4(2) . . ? O1 C4 C3 118.6(2) . . ? C6 C5 C3 120.7(2) . . ? C6 C5 H5 119.6 . . ? C3 C5 H5 119.6 . . ? N2 C6 C5 120.8(3) . . ? N2 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C4 N1 N1 106.75(14) . 3 ? O2 N2 C6 119.9(2) . . ? O2 N2 C1 120.3(2) . . ? C6 N2 C1 119.8(2) . . ? C4 O1 C4 102.7(3) . 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 N2 C1 C2 C3 0.0(4) . . . . ? C1 C2 C3 C5 1.1(4) . . . . ? C1 C2 C3 C4 -178.2(2) . . . . ? C5 C3 C4 N1 178.3(3) . . . . ? C2 C3 C4 N1 -2.4(4) . . . . ? C5 C3 C4 O1 -3.3(3) . . . . ? C2 C3 C4 O1 176.0(2) . . . . ? C2 C3 C5 C6 -0.6(4) . . . . ? C4 C3 C5 C6 178.7(2) . . . . ? C3 C5 C6 N2 -1.0(4) . . . . ? O1 C4 N1 N1 0.4(3) . . . 3 ? C3 C4 N1 N1 178.9(3) . . . 3 ? C5 C6 N2 O2 -179.0(2) . . . . ? C5 C6 N2 C1 2.2(4) . . . . ? C2 C1 N2 O2 179.4(2) . . . . ? C2 C1 N2 C6 -1.7(4) . . . . ? N1 C4 O1 C4 -0.18(14) . . . 3 ? C3 C4 O1 C4 -178.8(3) . . . 3 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.174 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.043