# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Gopal Das' _publ_contact_author_email GDAS@IITG.ERNET.IN _publ_section_title ; Aryl azo imidazoles assisted assembly of anion/anion-water through Organic-Inorganic hybrid ; loop_ _publ_author_name 'Gopal Das' 'Subhojit Majumdar' 'Avijit Pramanik' # Attachment 'all_cif.cif' data_salt1 _database_code_depnum_ccdc_archive 'CCDC 736670' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Br2 N9 O S' _chemical_formula_weight 579.30 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 12.1694(3) _cell_length_b 13.9841(4) _cell_length_c 14.3235(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.557(2) _cell_angle_gamma 90.00 _cell_volume 2348.24(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3968 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 20.52 _exptl_crystal_description reactangular _exptl_crystal_colour brown _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 3.572 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.271 _exptl_absorpt_correction_T_max 0.377 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 20047 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5728 _reflns_number_gt 5205 _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^)+(0.0405P)^2^+0.9292P] 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 ? _refine_ls_extinction_method none _refine_ls_number_reflns 5728 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.071 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 Br2 Br -0.43461(3) 0.11756(3) 0.19733(3) 0.07071(17) Uani 1 1 d . . . Br1 Br 0.67294(3) 0.85028(3) 0.04948(3) 0.07774(18) Uani 1 1 d . . . S1 S 0.32951(10) 0.04511(10) 0.28006(10) 0.0924(4) Uani 1 1 d . . . C16 C -0.2923(3) 0.1639(3) 0.1875(2) 0.0536(9) Uani 1 1 d . . . C17 C -0.2131(4) 0.1008(3) 0.1684(3) 0.0707(11) Uani 1 1 d . . . H17 H -0.2313 0.0363 0.1588 0.085 Uiso 1 1 calc R . . C18 C -0.1099(4) 0.1321(4) 0.1639(3) 0.0837(14) Uani 1 1 d . . . H18 H -0.0568 0.0896 0.1514 0.100 Uiso 1 1 calc R . . C14 C -0.1619(4) 0.2907(3) 0.1961(3) 0.0715(12) Uani 1 1 d . . . H14 H -0.1430 0.3551 0.2051 0.086 Uiso 1 1 calc R . . C15 C -0.2677(3) 0.2599(3) 0.2015(2) 0.0609(10) Uani 1 1 d . . . H15 H -0.3206 0.3024 0.2141 0.073 Uiso 1 1 calc R . . C13 C -0.0842(3) 0.2270(5) 0.1777(3) 0.0808(15) Uani 1 1 d . . . C12 C 0.3129(3) 0.4132(3) 0.1503(3) 0.0658(11) Uani 1 1 d . . . H12 H 0.3557 0.4642 0.1376 0.079 Uiso 1 1 calc R . . C10 C 0.1739(4) 0.3325(4) 0.1666(3) 0.0722(12) Uani 1 1 d . . . C11 C 0.3536(4) 0.3262(3) 0.1765(3) 0.0755(12) Uani 1 1 d . . . H11 H 0.4283 0.3054 0.1860 0.091 Uiso 1 1 calc R . . N8 N 0.0488(4) 0.2422(3) 0.1767(2) 0.1124(18) Uani 1 1 d . . . N7 N 0.0397(4) 0.3202(3) 0.1661(2) 0.0877(13) Uani 1 1 d . . . N6 N 0.2633(4) 0.2742(3) 0.1865(2) 0.0813(11) Uani 1 1 d . . . H6N H 0.2639 0.2149 0.2026 0.098 Uiso 1 1 calc R . . N5 N 0.2009(3) 0.4168(3) 0.1449(2) 0.0690(9) Uani 1 1 d . . . H5N H 0.1565 0.4655 0.1301 0.083 Uiso 1 1 calc R . . C7 C 0.5299(3) 0.7987(3) 0.0505(3) 0.0582(10) Uani 1 1 d . . . C9 C 0.3427(3) 0.8159(4) 0.0711(3) 0.0796(14) Uani 1 1 d . . . H9 H 0.2855 0.8539 0.0836 0.095 Uiso 1 1 calc R . . C6 C 0.5099(3) 0.7026(3) 0.0320(3) 0.0649(11) Uani 1 1 d . . . H6 H 0.5659 0.6643 0.0180 0.078 Uiso 1 1 calc R . . C5 C 0.4071(4) 0.6638(3) 0.0343(3) 0.0762(12) Uani 1 1 d . . . H5 H 0.3939 0.5988 0.0225 0.091 Uiso 1 1 calc R . . C8 C 0.4471(3) 0.8563(3) 0.0700(3) 0.0715(12) Uani 1 1 d . . . H8 H 0.4605 0.9211 0.0822 0.086 Uiso 1 1 calc R . . C4 C 0.3243(4) 0.7196(4) 0.0537(3) 0.0764(13) Uani 1 1 d . . . C3 C -0.0621(3) 0.5543(3) 0.1111(3) 0.0623(10) Uani 1 1 d . . . H3 H -0.0952 0.4983 0.1257 0.075 Uiso 1 1 calc R . . C1 C 0.0572(4) 0.6548(4) 0.0793(3) 0.0693(12) Uani 1 1 d . . . C2 C -0.1118(3) 0.6404(3) 0.0969(3) 0.0622(10) Uani 1 1 d . . . H2 H -0.1852 0.6549 0.1003 0.075 Uiso 1 1 calc R . . N4 N 0.2181(3) 0.6576(3) 0.0610(2) 0.0807(11) Uani 1 1 d . . . N2 N 0.0459(2) 0.5630(3) 0.1003(2) 0.0613(8) Uani 1 1 d . . . N3 N 0.1562(4) 0.7166(3) 0.0650(2) 0.0898(13) Uani 1 1 d . . . N1 N -0.0364(3) 0.7023(2) 0.0769(2) 0.0670(9) Uani 1 1 d . . . H1 H -0.0477 0.7623 0.0648 0.080 Uiso 1 1 calc R . . C19 C 0.2216(4) 0.0183(3) 0.1911(4) 0.0710(12) Uani 1 1 d . . . N9 N 0.1431(4) -0.0007(3) 0.1288(3) 0.1082(15) Uani 1 1 d . . . O1 O 0.0600(4) 0.1070(2) 0.9497(4) 0.0933(11) Uani 1 1 d . . . H20 H -0.005(4) 0.088(3) 0.925(3) 0.085(17) Uiso 1 1 d . . . H10 H 0.079(7) 0.089(7) 1.006(7) 0.21(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br2 0.0579(3) 0.0789(3) 0.0736(3) 0.0103(2) 0.0146(2) -0.0082(2) Br1 0.0520(2) 0.0875(3) 0.0950(4) -0.0027(3) 0.0218(2) -0.0128(2) S1 0.0697(7) 0.1002(10) 0.1070(10) -0.0067(8) 0.0230(7) -0.0178(7) C16 0.050(2) 0.066(3) 0.042(2) 0.0084(19) 0.0070(17) 0.0033(19) C17 0.069(3) 0.068(3) 0.073(3) -0.003(2) 0.014(2) 0.007(2) C18 0.062(3) 0.114(4) 0.074(3) -0.010(3) 0.016(2) 0.008(3) C14 0.085(3) 0.079(3) 0.051(3) 0.002(2) 0.020(2) -0.029(2) C15 0.071(3) 0.059(3) 0.055(2) 0.006(2) 0.022(2) 0.003(2) C13 0.044(2) 0.153(5) 0.049(3) -0.003(3) 0.020(2) -0.009(3) C12 0.053(2) 0.065(3) 0.082(3) -0.008(2) 0.024(2) -0.002(2) C10 0.064(3) 0.099(4) 0.056(3) -0.017(3) 0.020(2) -0.012(3) C11 0.066(3) 0.074(3) 0.088(3) -0.002(3) 0.024(2) 0.017(2) N8 0.212(6) 0.072(3) 0.051(2) 0.008(2) 0.033(3) 0.056(3) N7 0.139(4) 0.061(3) 0.052(2) -0.004(2) 0.007(2) 0.030(2) N6 0.125(3) 0.052(2) 0.076(3) -0.0050(19) 0.042(2) -0.019(2) N5 0.058(2) 0.073(2) 0.079(3) 0.005(2) 0.0223(18) 0.0114(18) C7 0.041(2) 0.080(3) 0.053(2) 0.008(2) 0.0117(18) -0.003(2) C9 0.050(2) 0.136(5) 0.056(3) -0.005(3) 0.019(2) 0.016(3) C6 0.054(2) 0.077(3) 0.067(3) 0.015(2) 0.022(2) 0.002(2) C5 0.069(3) 0.090(3) 0.074(3) 0.015(3) 0.026(2) -0.015(3) C8 0.062(3) 0.085(3) 0.069(3) -0.007(2) 0.019(2) 0.004(2) C4 0.058(3) 0.124(4) 0.046(3) 0.004(3) 0.013(2) -0.029(3) C3 0.057(2) 0.057(3) 0.073(3) 0.007(2) 0.016(2) -0.007(2) C1 0.061(3) 0.105(4) 0.043(2) -0.001(2) 0.016(2) -0.040(3) C2 0.050(2) 0.069(3) 0.069(3) 0.002(2) 0.0174(19) -0.007(2) N4 0.106(3) 0.073(3) 0.052(2) -0.0045(19) 0.002(2) 0.027(2) N2 0.0481(18) 0.083(3) 0.054(2) 0.0018(18) 0.0153(15) -0.0025(16) N3 0.133(4) 0.079(3) 0.047(2) -0.0045(19) 0.006(2) 0.039(3) N1 0.072(2) 0.063(2) 0.061(2) 0.0068(17) 0.0094(18) -0.0166(19) C19 0.067(3) 0.048(2) 0.105(4) -0.002(2) 0.034(3) -0.001(2) N9 0.092(3) 0.085(3) 0.132(4) -0.008(3) 0.003(3) 0.004(2) O1 0.085(3) 0.074(2) 0.116(3) 0.016(2) 0.018(2) -0.0213(19) _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 Br2 C16 1.889(4) . ? Br1 C7 1.888(3) . ? S1 C19 1.610(5) . ? C16 C15 1.377(5) . ? C16 C17 1.388(5) . ? C17 C18 1.348(6) . ? C18 C13 1.366(7) . ? C14 C13 1.376(6) . ? C14 C15 1.379(5) . ? C13 N8 1.635(6) . ? C12 C11 1.328(5) . ? C12 N5 1.345(4) . ? C10 N5 1.283(5) . ? C10 N6 1.327(5) . ? C10 N7 1.640(6) . ? C11 N6 1.357(5) . ? N8 N7 1.103(4) . ? C7 C8 1.375(5) . ? C7 C6 1.379(5) . ? C9 C4 1.377(6) . ? C9 C8 1.395(5) . ? C6 C5 1.372(5) . ? C5 C4 1.360(6) . ? C4 N4 1.583(6) . ? C3 C2 1.338(5) . ? C3 N2 1.369(4) . ? C1 N1 1.312(5) . ? C1 N2 1.333(5) . ? C1 N3 1.541(5) . ? C2 N1 1.346(5) . ? N4 N3 1.129(4) . ? C19 N9 1.150(5) . ? 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 C15 C16 C17 120.8(4) . . ? C15 C16 Br2 119.5(3) . . ? C17 C16 Br2 119.7(3) . . ? C18 C17 C16 120.5(4) . . ? C17 C18 C13 119.3(4) . . ? C13 C14 C15 120.5(4) . . ? C16 C15 C14 117.8(4) . . ? C18 C13 C14 120.9(4) . . ? C18 C13 N8 108.3(4) . . ? C14 C13 N8 130.6(5) . . ? C11 C12 N5 110.2(4) . . ? N5 C10 N6 111.6(4) . . ? N5 C10 N7 114.5(4) . . ? N6 C10 N7 133.9(5) . . ? C12 C11 N6 105.6(4) . . ? N7 N8 C13 93.9(5) . . ? N8 N7 C10 92.3(5) . . ? C10 N6 C11 106.7(4) . . ? C10 N5 C12 105.8(4) . . ? C8 C7 C6 120.6(4) . . ? C8 C7 Br1 120.4(3) . . ? C6 C7 Br1 119.1(3) . . ? C4 C9 C8 119.9(4) . . ? C5 C6 C7 119.7(4) . . ? C4 C5 C6 120.5(5) . . ? C7 C8 C9 119.0(4) . . ? C5 C4 C9 120.3(4) . . ? C5 C4 N4 111.2(5) . . ? C9 C4 N4 128.3(4) . . ? C2 C3 N2 108.1(3) . . ? N1 C1 N2 110.6(3) . . ? N1 C1 N3 114.7(4) . . ? N2 C1 N3 134.5(4) . . ? C3 C2 N1 107.8(4) . . ? N3 N4 C4 99.8(4) . . ? C1 N2 C3 105.7(3) . . ? N4 N3 C1 98.8(4) . . ? C1 N1 C2 107.7(4) . . ? N9 C19 S1 178.6(5) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.509 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.061 data_salt2 _database_code_depnum_ccdc_archive 'CCDC 736671' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 I N5 O4' _chemical_formula_weight 379.12 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 4.88350(10) _cell_length_b 10.1720(3) _cell_length_c 27.4296(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.328(2) _cell_angle_gamma 90.00 _cell_volume 1362.20(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4950 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 24.27 _exptl_crystal_description reactangular _exptl_crystal_colour red _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 2.372 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.389 _exptl_absorpt_correction_T_max 0.482 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 17507 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3278 _reflns_number_gt 2337 _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^)+(0.0301P)^2^+0.5228P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3278 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0752 _refine_ls_wR_factor_gt 0.0675 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.005 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 I1 I 0.76555(5) 0.71767(3) 0.197078(9) 0.05625(11) Uani 1 1 d . . . C1 C -0.3479(7) 0.8175(3) 0.41696(13) 0.0448(8) Uani 1 1 d . . . C2 C -0.6060(8) 0.7400(4) 0.47382(15) 0.0577(10) Uani 1 1 d . . . C3 C -0.6675(7) 0.8664(4) 0.46852(14) 0.0555(9) Uani 1 1 d . . . N1 N -0.4064(6) 0.7096(4) 0.44163(12) 0.0530(8) Uani 1 1 d . . . N2 N -0.5064(6) 0.9151(3) 0.43311(11) 0.0512(7) Uani 1 1 d . . . N4 N -0.0323(6) 0.7309(3) 0.37190(11) 0.0482(7) Uani 1 1 d . . . N3 N -0.1616(5) 0.8360(3) 0.38006(10) 0.0471(7) Uani 1 1 d . . . C7 C 0.5233(6) 0.7292(3) 0.25903(13) 0.0431(8) Uani 1 1 d . . . C5 C 0.2298(7) 0.8547(4) 0.30987(13) 0.0493(9) Uani 1 1 d . . . C4 C 0.1592(6) 0.7390(3) 0.33423(13) 0.0423(8) Uani 1 1 d . . . C8 C 0.4632(7) 0.6155(3) 0.28450(14) 0.0488(8) Uani 1 1 d . . . C9 C 0.2822(7) 0.6200(3) 0.32255(13) 0.0484(8) Uani 1 1 d . . . C6 C 0.4099(7) 0.8484(4) 0.27265(14) 0.0499(9) Uani 1 1 d . . . O2 O 0.0529(6) 0.6644(3) 0.10030(12) 0.0827(9) Uani 1 1 d . . . O3 O 0.2784(6) 0.8421(3) 0.08978(14) 0.0901(10) Uani 1 1 d . . . O1 O 0.7307(9) 0.4584(3) 0.43224(15) 0.0812(10) Uani 1 1 d . . . O4 O 0.4071(6) 0.6604(3) 0.05653(12) 0.0878(9) Uani 1 1 d . . . N5 N 0.2494(6) 0.7212(4) 0.08202(13) 0.0619(8) Uani 1 1 d . . . H1O H 0.879(12) 0.428(6) 0.425(2) 0.14(3) Uiso 1 1 d . . . H2O H 0.620(11) 0.421(6) 0.417(2) 0.11(2) Uiso 1 1 d . . . H1N H -0.328(8) 0.638(4) 0.4366(14) 0.068(13) Uiso 1 1 d . . . H2N H -0.514(8) 0.996(5) 0.4200(14) 0.084(15) Uiso 1 1 d . . . H3 H -0.798(7) 0.921(4) 0.4838(13) 0.061(11) Uiso 1 1 d . . . H2 H -0.675(8) 0.670(4) 0.4923(15) 0.073(13) Uiso 1 1 d . . . H9 H 0.241(6) 0.528(3) 0.3433(11) 0.051(9) Uiso 1 1 d . . . H8 H 0.542(6) 0.533(3) 0.2764(11) 0.052(9) Uiso 1 1 d . . . H5 H 0.146(7) 0.939(4) 0.3197(12) 0.064(11) Uiso 1 1 d . . . H6 H 0.451(7) 0.922(4) 0.2540(13) 0.061(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.05695(15) 0.05643(17) 0.05596(18) -0.00376(12) 0.01401(11) -0.00183(11) C1 0.0477(16) 0.046(2) 0.041(2) -0.0016(15) 0.0002(16) 0.0007(14) C2 0.064(2) 0.061(3) 0.048(2) 0.0067(19) 0.0095(19) -0.0069(19) C3 0.0567(19) 0.062(3) 0.048(2) -0.0056(19) 0.0113(18) 0.0054(19) N1 0.0573(16) 0.052(2) 0.050(2) 0.0040(16) 0.0062(15) 0.0078(16) N2 0.0578(16) 0.0497(19) 0.0463(18) -0.0027(15) 0.0071(14) 0.0083(15) N4 0.0526(15) 0.0470(17) 0.0450(18) -0.0008(13) 0.0037(13) 0.0035(13) N3 0.0530(15) 0.0461(16) 0.0423(17) -0.0035(14) 0.0033(13) 0.0060(14) C7 0.0421(15) 0.0438(19) 0.043(2) -0.0048(16) 0.0011(14) -0.0016(14) C5 0.0593(19) 0.0343(19) 0.055(2) 0.0015(17) 0.0044(18) 0.0036(16) C4 0.0472(16) 0.0359(18) 0.044(2) -0.0030(14) -0.0016(15) 0.0032(13) C8 0.0531(18) 0.0347(19) 0.059(2) -0.0028(17) 0.0064(17) 0.0019(15) C9 0.0576(19) 0.0373(19) 0.051(2) 0.0032(16) 0.0058(17) 0.0023(15) C6 0.0539(18) 0.039(2) 0.057(2) 0.0036(18) 0.0083(18) 0.0012(16) O2 0.0848(19) 0.0717(19) 0.094(2) -0.0220(17) 0.0481(17) -0.0221(16) O3 0.0747(18) 0.0528(19) 0.143(3) -0.008(2) 0.0138(18) -0.0093(15) O1 0.076(2) 0.0496(19) 0.119(3) 0.0050(18) 0.021(2) 0.0042(17) O4 0.0720(17) 0.087(2) 0.106(3) -0.015(2) 0.0408(18) -0.0081(17) N5 0.0541(17) 0.063(2) 0.069(2) -0.0030(19) 0.0111(17) -0.0052(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 I1 C7 2.096(4) . ? C1 N1 1.325(5) . ? C1 N2 1.340(4) . ? C1 N3 1.389(5) . ? C2 C3 1.327(6) . ? C2 N1 1.366(5) . ? C3 N2 1.357(5) . ? N4 N3 1.264(4) . ? N4 C4 1.412(5) . ? C7 C8 1.386(5) . ? C7 C6 1.388(5) . ? C5 C6 1.364(5) . ? C5 C4 1.400(5) . ? C4 C9 1.392(5) . ? C8 C9 1.384(5) . ? O2 N5 1.236(4) . ? O3 N5 1.255(4) . ? O4 N5 1.220(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 108.2(3) . . ? N1 C1 N3 129.6(3) . . ? N2 C1 N3 122.3(3) . . ? C3 C2 N1 108.2(4) . . ? C2 C3 N2 107.3(3) . . ? C1 N1 C2 107.9(4) . . ? C1 N2 C3 108.4(3) . . ? N3 N4 C4 114.9(3) . . ? N4 N3 C1 110.7(3) . . ? C8 C7 C6 120.2(3) . . ? C8 C7 I1 119.5(3) . . ? C6 C7 I1 120.2(3) . . ? C6 C5 C4 119.2(3) . . ? C9 C4 C5 120.6(3) . . ? C9 C4 N4 114.5(3) . . ? C5 C4 N4 125.0(3) . . ? C9 C8 C7 119.9(3) . . ? C8 C9 C4 119.3(3) . . ? C5 C6 C7 120.7(4) . . ? O4 N5 O2 120.1(4) . . ? O4 N5 O3 121.6(3) . . ? O2 N5 O3 118.3(3) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.800 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.077 data_salt3 _database_code_depnum_ccdc_archive 'CCDC 736672' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Cl I N4 O5' _chemical_formula_weight 416.56 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 5.60440(10) _cell_length_b 8.8412(2) _cell_length_c 29.3023(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.3470(10) _cell_angle_gamma 90.00 _cell_volume 1445.60(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7085 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.91 _exptl_crystal_description reactangular _exptl_crystal_colour red _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1101 _exptl_absorpt_coefficient_mu 2.426 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.389 _exptl_absorpt_correction_T_max 0.501 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 15694 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3537 _reflns_number_gt 2712 _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^)+(0.0555P)^2^+0.7526P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3537 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.177 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 I1 I 1.19287(5) 0.19985(3) 0.228248(9) 0.07237(13) Uani 1 1 d . . . Cl1 Cl 0.48367(16) 0.19049(9) 0.55762(3) 0.0619(2) Uani 1 1 d . . . C1 C 0.9602(6) 0.2074(4) 0.28011(12) 0.0564(8) Uani 1 1 d . . . C4 C 0.6950(6) 0.3494(4) 0.32307(13) 0.0617(8) Uani 1 1 d . . . H4 H 0.6274 0.4411 0.3306 0.074 Uiso 1 1 calc R . . C5 C 0.8593(7) 0.3450(4) 0.29137(14) 0.0636(8) Uani 1 1 d . . . H5 H 0.9037 0.4337 0.2773 0.076 Uiso 1 1 calc R . . C2 C 0.9004(7) 0.0761(4) 0.30189(13) 0.0699(9) Uani 1 1 d . . . H2 H 0.9719 -0.0152 0.2951 0.084 Uiso 1 1 calc R . . C3 C 0.7339(7) 0.0811(4) 0.33375(12) 0.0681(9) Uani 1 1 d . . . H3 H 0.6923 -0.0072 0.3484 0.082 Uiso 1 1 calc R . . C6 C 0.6292(6) 0.2165(4) 0.34395(11) 0.0541(7) Uani 1 1 d . . . N1 N 0.4541(6) 0.2081(3) 0.37548(10) 0.0570(7) Uani 1 1 d . . . C7 C 0.1750(6) 0.3168(4) 0.41180(11) 0.0543(7) Uani 1 1 d . . . N3 N 0.3450(5) 0.3303(3) 0.38035(10) 0.0563(6) Uani 1 1 d . . . C9 C -0.1178(6) 0.3849(4) 0.45198(12) 0.0611(8) Uani 1 1 d . . . H9 H -0.2367 0.4426 0.4637 0.073 Uiso 1 1 calc R . . C8 C -0.0592(7) 0.2400(5) 0.46314(14) 0.0656(9) Uani 1 1 d . . . H8 H -0.1289 0.1797 0.4842 0.079 Uiso 1 1 calc R . . N5 N 0.1214(6) 0.1996(3) 0.43755(11) 0.0610(7) Uani 1 1 d . . . N4 N 0.0308(5) 0.4300(4) 0.42023(11) 0.0586(7) Uani 1 1 d . . . O5 O 0.9964(7) 0.6935(3) 0.36871(12) 0.0809(8) Uani 1 1 d . . . O2 O 0.7010(6) 0.1081(4) 0.55794(14) 0.1056(11) Uani 1 1 d . . . O1 O 0.4760(8) 0.2541(6) 0.60199(15) 0.1332(15) Uani 1 1 d . . . O3 O 0.4816(8) 0.3063(4) 0.52478(15) 0.1095(12) Uani 1 1 d . . . O4 O 0.2811(6) 0.0985(4) 0.54941(15) 0.1188(13) Uani 1 1 d . . . H1O H 1.130(18) 0.750(10) 0.394(3) 0.20(3) Uiso 1 1 d . . . H3N H 0.194(7) 0.108(5) 0.4393(13) 0.068(10) Uiso 1 1 d . . . H4N H 0.047(7) 0.512(5) 0.4085(14) 0.075(13) Uiso 1 1 d . . . H5O H 0.852(11) 0.722(5) 0.3689(19) 0.138(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0768(2) 0.0713(2) 0.0722(2) -0.00688(11) 0.02410(13) -0.01110(11) Cl1 0.0588(5) 0.0605(5) 0.0684(5) 0.0032(4) 0.0159(4) 0.0098(3) C1 0.0600(19) 0.0562(19) 0.0530(18) -0.0019(14) 0.0058(14) -0.0011(14) C4 0.066(2) 0.0511(17) 0.068(2) -0.0023(16) 0.0076(16) 0.0070(15) C5 0.072(2) 0.0489(17) 0.071(2) 0.0045(16) 0.0106(17) -0.0037(15) C2 0.087(3) 0.054(2) 0.073(2) 0.0042(17) 0.0260(18) 0.0112(17) C3 0.090(3) 0.0508(19) 0.067(2) 0.0111(16) 0.0243(18) 0.0121(17) C6 0.0595(19) 0.0557(19) 0.0462(16) 0.0005(13) 0.0008(13) 0.0058(14) N1 0.0647(17) 0.0540(16) 0.0526(16) 0.0018(12) 0.0063(12) 0.0096(12) C7 0.0556(18) 0.0574(19) 0.0492(17) -0.0039(14) 0.0006(13) 0.0060(13) N3 0.0603(16) 0.0501(15) 0.0582(16) -0.0001(12) 0.0035(12) 0.0051(12) C9 0.0600(19) 0.061(2) 0.062(2) -0.0083(16) 0.0056(15) 0.0088(15) C8 0.067(2) 0.072(2) 0.0588(19) 0.0028(17) 0.0122(15) 0.0085(18) N5 0.0683(19) 0.0580(18) 0.0570(17) 0.0041(13) 0.0071(13) 0.0164(14) N4 0.0632(17) 0.0491(16) 0.0636(18) -0.0023(13) 0.0062(13) 0.0068(12) O5 0.080(2) 0.0719(19) 0.093(2) 0.0058(14) 0.0188(17) 0.0039(15) O2 0.093(2) 0.085(2) 0.146(3) 0.036(2) 0.047(2) 0.0394(17) O1 0.103(3) 0.200(4) 0.100(3) -0.059(3) 0.030(2) -0.007(3) O3 0.108(3) 0.083(2) 0.142(3) 0.043(2) 0.038(2) 0.0220(17) O4 0.090(2) 0.109(3) 0.152(3) 0.023(2) -0.010(2) -0.026(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 I1 C1 2.094(4) . ? Cl1 O4 1.399(3) . ? Cl1 O3 1.404(3) . ? Cl1 O2 1.418(3) . ? Cl1 O1 1.421(4) . ? C1 C2 1.381(5) . ? C1 C5 1.394(5) . ? C4 C5 1.368(5) . ? C4 C6 1.391(5) . ? C2 C3 1.381(5) . ? C3 C6 1.378(5) . ? C6 N1 1.411(5) . ? N1 N3 1.256(4) . ? C7 N4 1.324(4) . ? C7 N5 1.332(5) . ? C7 N3 1.391(5) . ? C9 C8 1.355(5) . ? C9 N4 1.365(5) . ? C8 N5 1.362(5) . ? 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 O4 Cl1 O3 110.6(2) . . ? O4 Cl1 O2 112.7(2) . . ? O3 Cl1 O2 109.3(2) . . ? O4 Cl1 O1 107.1(3) . . ? O3 Cl1 O1 109.8(3) . . ? O2 Cl1 O1 107.2(3) . . ? C2 C1 C5 120.2(3) . . ? C2 C1 I1 120.2(3) . . ? C5 C1 I1 119.6(3) . . ? C5 C4 C6 119.8(3) . . ? C4 C5 C1 119.9(3) . . ? C1 C2 C3 119.6(3) . . ? C6 C3 C2 120.2(3) . . ? C3 C6 C4 120.2(3) . . ? C3 C6 N1 115.6(3) . . ? C4 C6 N1 124.2(3) . . ? N3 N1 C6 113.9(3) . . ? N4 C7 N5 108.0(3) . . ? N4 C7 N3 121.7(3) . . ? N5 C7 N3 130.3(3) . . ? N1 N3 C7 111.8(3) . . ? C8 C9 N4 106.9(3) . . ? C9 C8 N5 106.9(4) . . ? C7 N5 C8 109.0(3) . . ? C7 N4 C9 109.1(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.631 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.105 data_salt4 _database_code_depnum_ccdc_archive 'CCDC 736673' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 N5 O3' _chemical_formula_weight 285.27 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 6.8263(2) _cell_length_b 11.5549(3) _cell_length_c 17.0562(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.7880(10) _cell_angle_gamma 90.00 _cell_volume 1335.92(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4282 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 25.25 _exptl_crystal_description reactangular _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 16102 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3238 _reflns_number_gt 2780 _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^)+(0.0594P)^2^+0.1825P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3238 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1473 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.055 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 C13 C 0.1862(2) 0.88116(18) 0.92207(11) 0.0676(5) Uani 1 1 d . . . C4 C 0.2297(3) 0.91298(17) 1.00238(11) 0.0678(5) Uani 1 1 d . . . C8 C 0.1496(3) 0.76336(19) 0.90409(12) 0.0737(5) Uani 1 1 d . . . C12 C 0.1775(3) 0.9624(2) 0.85846(12) 0.0782(6) Uani 1 1 d . . . H12 H 0.2017 1.0405 0.8686 0.094 Uiso 1 1 calc R . . C5 C 0.2344(3) 0.83150(19) 1.06090(13) 0.0809(6) Uani 1 1 d . . . H5 H 0.2627 0.8540 1.1134 0.097 Uiso 1 1 calc R . . C11 C 0.1332(3) 0.9239(2) 0.78243(13) 0.0910(7) Uani 1 1 d . . . H11 H 0.1260 0.9769 0.7411 0.109 Uiso 1 1 calc R . . C9 C 0.1078(3) 0.7287(2) 0.82447(16) 0.0941(7) Uani 1 1 d . . . H9 H 0.0863 0.6508 0.8125 0.113 Uiso 1 1 calc R . . C6 C 0.1974(3) 0.7156(2) 1.04279(15) 0.0892(6) Uani 1 1 d . . . H6 H 0.2006 0.6614 1.0832 0.107 Uiso 1 1 calc R . . C10 C 0.0987(3) 0.8069(3) 0.76569(16) 0.0981(7) Uani 1 1 d . . . H10 H 0.0693 0.7828 0.7136 0.118 Uiso 1 1 calc R . . C1 C 0.3402(3) 1.17549(18) 1.10012(12) 0.0670(5) Uani 1 1 d . . . C2 C 0.4084(3) 1.3354(2) 1.16540(15) 0.0867(6) Uani 1 1 d . . . H2 H 0.4391 1.3870 1.2069 0.104 Uiso 1 1 calc R . . C3 C 0.3811(3) 1.3614(2) 1.08824(15) 0.0859(6) Uani 1 1 d . . . H3 H 0.3898 1.4346 1.0662 0.103 Uiso 1 1 calc R . . N3 N 0.3064(2) 1.05834(15) 1.08894(10) 0.0715(4) Uani 1 1 d . . . N4 N 0.2673(2) 1.03282(14) 1.01703(10) 0.0707(4) Uani 1 1 d . . . N1 N 0.3828(2) 1.21975(17) 1.17143(10) 0.0773(5) Uani 1 1 d . . . H1N H 0.3928 1.1812 1.2149 0.093 Uiso 1 1 calc R . . N2 N 0.3385(2) 1.26151(16) 1.04853(10) 0.0754(5) Uani 1 1 d . . . H2N H 0.3142 1.2548 0.9981 0.091 Uiso 1 1 calc R . . C7 C 0.1566(3) 0.6811(2) 0.96661(16) 0.0895(7) Uani 1 1 d . . . H7 H 0.1330 0.6033 0.9551 0.107 Uiso 1 1 calc R . . N5 N 0.3364(3) 0.1399(2) 0.35924(12) 0.0910(6) Uani 1 1 d . . . O2 O 0.3256(3) 0.24366(17) 0.36159(11) 0.1165(6) Uani 1 1 d . . . O3 O 0.3977(3) 0.08882(16) 0.30331(10) 0.1228(7) Uani 1 1 d . . . O1 O 0.2866(4) 0.0826(2) 0.41343(13) 0.1576(9) 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 C13 0.0443(10) 0.0836(14) 0.0750(13) -0.0015(11) 0.0068(8) 0.0065(9) C4 0.0518(10) 0.0794(14) 0.0728(13) 0.0049(10) 0.0098(8) 0.0074(9) C8 0.0483(11) 0.0910(15) 0.0819(14) -0.0071(12) 0.0073(9) 0.0002(9) C12 0.0603(12) 0.0959(15) 0.0777(14) 0.0038(12) 0.0053(9) 0.0075(10) C5 0.0781(14) 0.0869(16) 0.0786(14) 0.0073(12) 0.0140(10) 0.0056(11) C11 0.0731(14) 0.124(2) 0.0736(15) 0.0071(13) 0.0002(10) 0.0106(13) C9 0.0650(14) 0.1106(19) 0.1060(19) -0.0194(16) 0.0066(12) -0.0092(12) C6 0.0888(16) 0.0887(17) 0.0917(17) 0.0131(13) 0.0178(12) 0.0023(12) C10 0.0715(15) 0.134(2) 0.0856(17) -0.0164(17) -0.0037(11) -0.0017(14) C1 0.0523(10) 0.0767(14) 0.0729(13) 0.0022(11) 0.0113(8) 0.0114(9) C2 0.0738(14) 0.0851(17) 0.1018(19) -0.0134(13) 0.0130(12) 0.0053(11) C3 0.0801(15) 0.0794(15) 0.1007(18) 0.0008(13) 0.0203(12) 0.0030(11) N3 0.0578(9) 0.0870(13) 0.0700(11) -0.0010(9) 0.0092(7) 0.0081(8) N4 0.0543(9) 0.0857(12) 0.0721(11) 0.0004(9) 0.0079(7) 0.0091(8) N1 0.0693(11) 0.0939(14) 0.0690(11) -0.0009(9) 0.0092(8) 0.0102(9) N2 0.0658(10) 0.0885(12) 0.0723(11) 0.0018(10) 0.0097(8) 0.0063(8) C7 0.0699(14) 0.0851(15) 0.115(2) -0.0024(14) 0.0161(12) -0.0041(11) N5 0.0968(14) 0.0976(16) 0.0754(13) -0.0043(12) -0.0033(10) 0.0105(11) O2 0.1209(15) 0.0883(12) 0.1323(16) -0.0223(10) -0.0186(11) 0.0050(10) O3 0.1827(19) 0.1129(14) 0.0749(11) 0.0008(9) 0.0239(11) 0.0510(12) O1 0.243(3) 0.1414(18) 0.0966(14) 0.0113(13) 0.0536(15) -0.0050(16) _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 C13 C8 1.411(3) . ? C13 C4 1.416(3) . ? C13 C12 1.430(3) . ? C4 C5 1.370(3) . ? C4 N4 1.425(2) . ? C8 C9 1.412(3) . ? C8 C7 1.425(3) . ? C12 C11 1.370(3) . ? C5 C6 1.390(3) . ? C11 C10 1.397(3) . ? C9 C10 1.346(3) . ? C6 C7 1.357(3) . ? C1 N1 1.320(2) . ? C1 N2 1.327(2) . ? C1 N3 1.383(2) . ? C2 C3 1.342(3) . ? C2 N1 1.353(3) . ? C3 N2 1.353(3) . ? N3 N4 1.259(2) . ? N5 O2 1.203(2) . ? N5 O1 1.217(2) . ? N5 O3 1.236(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C13 C4 118.19(18) . . ? C8 C13 C12 118.53(19) . . ? C4 C13 C12 123.28(19) . . ? C5 C4 C13 120.72(19) . . ? C5 C4 N4 123.49(19) . . ? C13 C4 N4 115.79(17) . . ? C13 C8 C9 119.6(2) . . ? C13 C8 C7 119.4(2) . . ? C9 C8 C7 121.0(2) . . ? C11 C12 C13 119.3(2) . . ? C4 C5 C6 120.8(2) . . ? C12 C11 C10 121.4(2) . . ? C10 C9 C8 120.8(2) . . ? C7 C6 C5 120.5(2) . . ? C9 C10 C11 120.4(2) . . ? N1 C1 N2 107.73(19) . . ? N1 C1 N3 121.44(19) . . ? N2 C1 N3 130.83(19) . . ? C3 C2 N1 107.0(2) . . ? C2 C3 N2 107.2(2) . . ? N4 N3 C1 112.11(16) . . ? N3 N4 C4 114.30(16) . . ? C1 N1 C2 109.21(18) . . ? C1 N2 C3 108.83(18) . . ? C6 C7 C8 120.3(2) . . ? O2 N5 O1 119.6(2) . . ? O2 N5 O3 122.0(2) . . ? O1 N5 O3 118.5(2) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.290 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.029 data_salt5 _database_code_depnum_ccdc_archive 'CCDC 736674' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 N9 O4' _chemical_formula_weight 525.53 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' S S 0.1246 0.1234 '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 5.6061(2) _cell_length_b 15.8135(6) _cell_length_c 14.0347(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.281(2) _cell_angle_gamma 90.00 _cell_volume 1234.17(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1534 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 23.27 _exptl_crystal_description recetangular _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 0.935 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13175 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5753 _reflns_number_gt 2896 _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^)+(0.0618P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5753 _refine_ls_number_parameters 373 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.084 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 C10 C 0.9499(7) 0.2453(3) 0.9038(3) 0.0381(10) Uani 1 1 d . . . C1 C 0.7378(7) 0.2745(3) 0.8480(3) 0.0428(11) Uani 1 1 d . . . C5 C 1.0777(7) 0.1771(3) 0.8668(3) 0.0430(12) Uani 1 1 d . . . C9 C 1.0421(7) 0.2798(3) 0.9946(3) 0.0484(12) Uani 1 1 d . . . H9 H 0.9600 0.3236 1.0204 0.058 Uiso 1 1 calc R . . C6 C 1.2905(7) 0.1467(3) 0.9207(3) 0.0491(12) Uani 1 1 d . . . H6 H 1.3744 0.1020 0.8974 0.059 Uiso 1 1 calc R . . C2 C 0.6583(8) 0.2384(3) 0.7617(3) 0.0573(14) Uani 1 1 d . . . H2 H 0.5212 0.2596 0.7252 0.069 Uiso 1 1 calc R . . C4 C 0.9852(8) 0.1410(3) 0.7777(3) 0.0555(14) Uani 1 1 d . . . H4 H 1.0669 0.0965 0.7531 0.067 Uiso 1 1 calc R . . C7 C 1.3728(8) 0.1827(3) 1.0067(3) 0.0571(14) Uani 1 1 d . . . H7 H 1.5138 0.1626 1.0413 0.068 Uiso 1 1 calc R . . C8 C 1.2493(7) 0.2496(3) 1.0442(3) 0.0541(13) Uani 1 1 d . . . H8 H 1.3090 0.2734 1.1030 0.065 Uiso 1 1 calc R . . C3 C 0.7799(8) 0.1701(3) 0.7274(3) 0.0577(13) Uani 1 1 d . . . H3 H 0.7194 0.1444 0.6698 0.069 Uiso 1 1 calc R . . C11 C 0.3092(7) 0.4289(3) 0.8845(3) 0.0421(10) Uani 1 1 d . . . C12 C 0.0298(8) 0.5156(4) 0.9103(4) 0.0647(14) Uani 1 1 d . . . H12 H -0.1074 0.5492 0.9007 0.078 Uiso 1 1 calc R . . C13 C 0.1770(8) 0.5108(3) 0.9928(3) 0.0585(13) Uani 1 1 d . . . H13 H 0.1609 0.5386 1.0500 0.070 Uiso 1 1 calc R . . N3 N 0.4340(6) 0.3691(2) 0.8371(2) 0.0470(9) Uani 1 1 d . . . N4 N 0.6155(6) 0.3405(2) 0.8904(2) 0.0439(9) Uani 1 1 d . . . N1 N 0.1084(6) 0.4641(3) 0.8413(2) 0.0534(11) Uani 1 1 d . . . N2 N 0.3540(6) 0.4570(3) 0.9758(2) 0.0533(10) Uani 1 1 d . . . C23 C 0.9518(7) 0.1446(3) 0.4022(3) 0.0419(11) Uani 1 1 d . . . C14 C 0.7393(7) 0.1152(3) 0.3438(3) 0.0422(11) Uani 1 1 d . . . C18 C 1.0835(7) 0.2113(3) 0.3664(3) 0.0454(12) Uani 1 1 d . . . C19 C 1.2947(7) 0.2404(3) 0.4228(3) 0.0550(13) Uani 1 1 d . . . H19 H 1.3821 0.2845 0.4003 0.066 Uiso 1 1 calc R . . C15 C 0.6635(8) 0.1537(3) 0.2565(3) 0.0531(13) Uani 1 1 d . . . H15 H 0.5221 0.1360 0.2201 0.064 Uiso 1 1 calc R . . C22 C 1.0346(8) 0.1097(3) 0.4927(3) 0.0502(12) Uani 1 1 d . . . H22 H 0.9501 0.0660 0.5176 0.060 Uiso 1 1 calc R . . C20 C 1.3703(8) 0.2051(3) 0.5082(3) 0.0545(13) Uani 1 1 d . . . H20 H 1.5113 0.2242 0.5438 0.065 Uiso 1 1 calc R . . C17 C 1.0010(7) 0.2482(3) 0.2765(3) 0.0558(14) Uani 1 1 d . . . H17 H 1.0860 0.2928 0.2537 0.067 Uiso 1 1 calc R . . C21 C 1.2405(8) 0.1406(4) 0.5438(3) 0.0594(15) Uani 1 1 d . . . H21 H 1.2941 0.1177 0.6038 0.071 Uiso 1 1 calc R . . C16 C 0.7988(9) 0.2191(4) 0.2231(3) 0.0668(14) Uani 1 1 d . . . H16 H 0.7495 0.2430 0.1633 0.080 Uiso 1 1 calc R . . C24 C 0.3083(7) -0.0385(3) 0.3780(3) 0.0455(11) Uani 1 1 d . . . C26 C 0.0242(8) -0.1255(3) 0.4000(3) 0.0566(13) Uani 1 1 d . . . H26 H -0.1157 -0.1576 0.3899 0.068 Uiso 1 1 calc R . . C25 C 0.1830(8) -0.1236(3) 0.4812(3) 0.0592(13) Uani 1 1 d . . . H25 H 0.1722 -0.1545 0.5368 0.071 Uiso 1 1 calc R . . N8 N 0.6113(6) 0.0505(2) 0.3840(2) 0.0484(10) Uani 1 1 d . . . N7 N 0.4295(6) 0.0230(2) 0.3313(2) 0.0467(9) Uani 1 1 d . . . N6 N 0.1069(6) -0.0721(3) 0.3360(3) 0.0528(11) Uani 1 1 d . . . N5 N 0.3624(6) -0.0680(3) 0.4666(2) 0.0500(9) Uani 1 1 d . . . O4 O 0.7136(6) 0.9618(3) 0.6252(2) 0.0720(9) Uani 1 1 d . . . O3 O 0.2183(5) 0.9447(2) 0.7057(2) 0.0898(9) Uani 1 1 d . . . N9 N 0.3145(8) 0.9368(3) 0.7910(3) 0.0810(11) Uani 1 1 d . . . O2 O 0.5360(7) 0.9408(5) 0.8045(2) 0.164(2) Uani 1 1 d . . . O1 O 0.2130(8) 0.9273(3) 0.8597(3) 0.1207(16) Uani 1 1 d . . . H6N H 0.036(7) -0.062(4) 0.278(3) 0.086(15) Uiso 1 1 d . . . H5N H 0.516(10) -0.048(5) 0.518(4) 0.14(2) Uiso 1 1 d . . . H2N H 0.462(5) 0.442(3) 1.019(2) 0.037(9) Uiso 1 1 d . . . H4OB H 0.629(6) 0.951(4) 0.689(3) 0.070(12) Uiso 1 1 d . . . H4OA H 0.873(8) 0.948(4) 0.666(3) 0.120(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C10 0.039(2) 0.039(3) 0.037(2) 0.001(2) 0.0087(17) -0.009(2) C1 0.043(2) 0.044(3) 0.042(2) -0.001(2) 0.0046(19) -0.001(2) C5 0.039(2) 0.044(3) 0.047(2) 0.006(2) 0.0062(19) 0.006(2) C9 0.044(2) 0.055(3) 0.046(2) -0.009(2) 0.0047(19) -0.002(2) C6 0.052(3) 0.041(3) 0.055(3) 0.001(2) 0.011(2) 0.006(2) C2 0.056(3) 0.069(4) 0.045(3) -0.003(3) -0.002(2) 0.016(3) C4 0.072(4) 0.043(3) 0.050(2) -0.014(2) 0.000(2) 0.010(2) C7 0.042(3) 0.069(4) 0.057(3) 0.008(3) -0.005(2) 0.002(3) C8 0.058(3) 0.058(4) 0.042(3) -0.005(2) -0.010(2) 0.000(3) C3 0.056(3) 0.069(4) 0.044(3) -0.023(3) -0.009(2) 0.012(3) C11 0.040(2) 0.040(3) 0.045(2) 0.000(2) 0.0023(17) 0.002(2) C12 0.051(3) 0.058(4) 0.087(3) -0.003(3) 0.014(3) 0.010(3) C13 0.052(3) 0.061(4) 0.064(3) -0.011(2) 0.013(2) 0.012(3) N3 0.044(2) 0.049(3) 0.048(2) 0.0012(18) 0.0071(17) 0.004(2) N4 0.0385(19) 0.045(3) 0.047(2) -0.0059(17) 0.0019(15) 0.0030(18) N1 0.044(2) 0.055(3) 0.061(2) -0.008(2) 0.0056(17) 0.003(2) N2 0.056(2) 0.053(3) 0.049(2) -0.003(2) -0.0034(17) 0.002(2) C23 0.039(2) 0.048(3) 0.039(2) -0.004(2) 0.0044(17) -0.002(2) C14 0.041(2) 0.044(3) 0.043(2) -0.004(2) 0.0071(18) 0.000(2) C18 0.051(3) 0.041(3) 0.043(2) -0.003(2) 0.005(2) 0.004(2) C19 0.046(3) 0.062(4) 0.056(3) -0.004(3) 0.003(2) -0.007(3) C15 0.047(3) 0.059(3) 0.049(3) 0.014(2) -0.010(2) -0.006(2) C22 0.053(3) 0.052(3) 0.046(2) 0.000(2) 0.006(2) 0.001(2) C20 0.055(3) 0.058(4) 0.049(3) -0.007(2) 0.001(2) -0.011(3) C17 0.052(3) 0.065(4) 0.051(3) 0.001(3) 0.007(2) -0.010(3) C21 0.046(3) 0.083(4) 0.047(3) -0.001(3) 0.001(2) -0.006(3) C16 0.072(3) 0.071(4) 0.053(3) 0.010(3) -0.006(2) -0.011(3) C24 0.043(2) 0.046(3) 0.048(2) 0.000(2) 0.0071(18) -0.001(3) C26 0.053(3) 0.051(3) 0.065(3) 0.007(3) 0.004(2) -0.014(2) C25 0.066(3) 0.050(3) 0.063(3) 0.011(2) 0.010(2) 0.000(3) N8 0.042(2) 0.054(3) 0.049(2) -0.0039(19) 0.0060(16) -0.0033(19) N7 0.044(2) 0.047(3) 0.048(2) -0.0015(18) -0.0002(17) -0.003(2) N6 0.051(2) 0.054(3) 0.052(2) -0.008(2) 0.0012(18) -0.011(2) N5 0.0434(19) 0.052(3) 0.055(2) 0.006(2) 0.0060(16) -0.003(2) O4 0.0666(16) 0.094(3) 0.0518(16) 0.0019(17) -0.0054(14) -0.0049(17) O3 0.083(2) 0.111(2) 0.0708(18) -0.002(2) -0.0083(15) 0.006(2) N9 0.091(3) 0.077(3) 0.076(3) -0.004(2) 0.014(2) -0.005(2) O2 0.093(3) 0.300(6) 0.094(2) -0.001(4) -0.011(2) -0.020(4) O1 0.197(4) 0.082(3) 0.100(3) -0.012(3) 0.088(3) -0.023(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 C10 C1 1.416(5) . ? C10 C9 1.422(5) . ? C10 C5 1.429(5) . ? C1 C2 1.362(5) . ? C1 N4 1.419(5) . ? C5 C4 1.411(5) . ? C5 C6 1.414(5) . ? C9 C8 1.363(6) . ? C6 C7 1.361(6) . ? C2 C3 1.396(6) . ? C4 C3 1.352(5) . ? C7 C8 1.403(6) . ? C11 N1 1.331(5) . ? C11 N2 1.348(5) . ? C11 N3 1.394(5) . ? C12 C13 1.336(6) . ? C12 N1 1.380(5) . ? C13 N2 1.351(5) . ? N3 N4 1.268(4) . ? C23 C22 1.409(6) . ? C23 C18 1.415(6) . ? C23 C14 1.435(5) . ? C14 C15 1.384(5) . ? C14 N8 1.408(5) . ? C18 C17 1.414(6) . ? C18 C19 1.414(5) . ? C19 C20 1.342(6) . ? C15 C16 1.399(6) . ? C22 C21 1.369(6) . ? C20 C21 1.383(6) . ? C17 C16 1.357(6) . ? C24 N6 1.318(5) . ? C24 N5 1.328(5) . ? C24 N7 1.395(5) . ? C26 C25 1.355(6) . ? C26 N6 1.357(5) . ? C25 N5 1.370(5) . ? N8 N7 1.259(4) . ? O3 N9 1.256(4) . ? N9 O1 1.189(4) . ? N9 O2 1.234(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C10 C9 123.7(4) . . ? C1 C10 C5 118.0(4) . . ? C9 C10 C5 118.3(4) . . ? C2 C1 C10 120.8(4) . . ? C2 C1 N4 124.0(4) . . ? C10 C1 N4 115.1(3) . . ? C4 C5 C6 121.8(4) . . ? C4 C5 C10 118.8(4) . . ? C6 C5 C10 119.3(4) . . ? C8 C9 C10 120.8(5) . . ? C7 C6 C5 120.0(4) . . ? C1 C2 C3 120.8(4) . . ? C3 C4 C5 121.2(4) . . ? C6 C7 C8 121.4(4) . . ? C9 C8 C7 120.1(4) . . ? C4 C3 C2 120.3(4) . . ? N1 C11 N2 109.9(4) . . ? N1 C11 N3 120.8(4) . . ? N2 C11 N3 129.2(4) . . ? C13 C12 N1 110.9(4) . . ? C12 C13 N2 105.6(4) . . ? N4 N3 C11 112.0(3) . . ? N3 N4 C1 114.2(3) . . ? C11 N1 C12 104.7(3) . . ? C11 N2 C13 108.8(4) . . ? C22 C23 C18 119.0(4) . . ? C22 C23 C14 122.9(4) . . ? C18 C23 C14 118.1(4) . . ? C15 C14 N8 124.0(4) . . ? C15 C14 C23 120.2(4) . . ? N8 C14 C23 115.7(3) . . ? C17 C18 C19 121.4(4) . . ? C17 C18 C23 119.8(4) . . ? C19 C18 C23 118.8(4) . . ? C20 C19 C18 120.8(5) . . ? C14 C15 C16 120.2(4) . . ? C21 C22 C23 119.4(5) . . ? C19 C20 C21 120.6(4) . . ? C16 C17 C18 120.6(5) . . ? C22 C21 C20 121.4(4) . . ? C17 C16 C15 121.1(5) . . ? N6 C24 N5 111.0(4) . . ? N6 C24 N7 120.8(4) . . ? N5 C24 N7 128.1(4) . . ? C25 C26 N6 107.4(4) . . ? C26 C25 N5 107.8(4) . . ? N7 N8 C14 115.6(3) . . ? N8 N7 C24 111.8(4) . . ? C24 N6 C26 107.5(4) . . ? C24 N5 C25 106.3(4) . . ? O1 N9 O2 117.2(4) . . ? O1 N9 O3 126.4(5) . . ? O2 N9 O3 116.3(4) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.205 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.038