# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_cm09-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 I N3' _chemical_formula_sum 'C12 H8 I N3' _chemical_formula_weight 321.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' 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 9.8821(3) _cell_length_b 7.5462(2) _cell_length_c 14.9402(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.517(3) _cell_angle_gamma 90.00 _cell_volume 1095.40(6) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3113 _cell_measurement_theta_min 4.5348 _cell_measurement_theta_max 73.8445 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4986 _exptl_crystal_size_mid 0.2473 _exptl_crystal_size_min 0.1987 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.947 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 22.751 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.018 _exptl_absorpt_correction_T_max 0.205 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 3982 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.98 _diffrn_reflns_theta_max 74.03 _reflns_number_total 2160 _reflns_number_gt 2015 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0717P)^2^+0.4096P] 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 2160 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 I I 0.01119(2) 0.79969(3) 0.601790(14) 0.02896(13) Uani 1 1 d . . . N1 N 0.3348(3) 1.0156(4) 0.4368(2) 0.0235(5) Uani 1 1 d . . . N2 N 0.3270(3) 1.0279(4) 0.5221(2) 0.0236(6) Uani 1 1 d . . . N3 N 0.3200(3) 0.8606(4) 0.5568(2) 0.0226(5) Uani 1 1 d . . . C1 C 0.3343(3) 0.8392(5) 0.4133(2) 0.0201(6) Uani 1 1 d . . . C2 C 0.3469(3) 0.7565(5) 0.3307(2) 0.0240(6) Uani 1 1 d . . . H2A H 0.3555 0.8236 0.2782 0.029 Uiso 1 1 calc R . . C3 C 0.3462(3) 0.5734(5) 0.3293(2) 0.0258(7) Uani 1 1 d . . . H3A H 0.3550 0.5134 0.2747 0.031 Uiso 1 1 calc R . . C4 C 0.3326(3) 0.4727(5) 0.4076(3) 0.0271(7) Uani 1 1 d . . . H4A H 0.3303 0.3470 0.4036 0.033 Uiso 1 1 calc R . . C5 C 0.3226(4) 0.5525(5) 0.4891(2) 0.0254(7) Uani 1 1 d . . . H5A H 0.3149 0.4851 0.5417 0.031 Uiso 1 1 calc R . . C6 C 0.3244(3) 0.7383(5) 0.4906(2) 0.0217(6) Uani 1 1 d . . . C7 C 0.3239(4) 0.8317(4) 0.6517(2) 0.0218(6) Uani 1 1 d . . . C8 C 0.2037(4) 0.8000(4) 0.6858(3) 0.0224(7) Uani 1 1 d . . . C9 C 0.2137(4) 0.7728(5) 0.7793(3) 0.0239(7) Uani 1 1 d . . . H9A H 0.1330 0.7512 0.8037 0.029 Uiso 1 1 calc R . . C10 C 0.3415(4) 0.7770(5) 0.8368(3) 0.0263(7) Uani 1 1 d . . . H10A H 0.3474 0.7577 0.9003 0.032 Uiso 1 1 calc R . . C11 C 0.4596(4) 0.8089(5) 0.8024(3) 0.0265(8) Uani 1 1 d . . . H11A H 0.5463 0.8116 0.8423 0.032 Uiso 1 1 calc R . . C12 C 0.4524(4) 0.8371(5) 0.7098(3) 0.0259(7) Uani 1 1 d . . . H12A H 0.5336 0.8597 0.6860 0.031 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 I 0.02210(17) 0.03898(19) 0.02475(18) 0.00475(7) 0.00150(10) -0.00408(8) N1 0.0252(13) 0.0212(13) 0.0256(14) 0.0028(11) 0.0084(10) 0.0016(11) N2 0.0256(13) 0.0204(14) 0.0261(14) 0.0012(11) 0.0082(10) -0.0004(11) N3 0.0261(13) 0.0190(13) 0.0237(14) 0.0006(11) 0.0072(11) -0.0005(11) C1 0.0186(14) 0.0219(15) 0.0208(16) 0.0009(12) 0.0063(11) 0.0015(12) C2 0.0214(15) 0.0269(16) 0.0241(17) -0.0012(14) 0.0047(12) 0.0003(14) C3 0.0234(15) 0.0279(17) 0.0266(16) -0.0045(13) 0.0057(12) -0.0011(13) C4 0.0261(15) 0.0206(16) 0.0348(19) -0.0043(14) 0.0060(13) -0.0029(13) C5 0.0273(15) 0.0221(16) 0.0271(17) 0.0044(13) 0.0053(13) -0.0014(12) C6 0.0201(15) 0.0225(16) 0.0231(17) 0.0000(13) 0.0057(12) -0.0016(13) C7 0.0252(16) 0.0179(14) 0.0235(17) -0.0004(12) 0.0078(13) 0.0010(12) C8 0.0206(16) 0.0226(16) 0.0248(17) 0.0003(11) 0.0060(13) -0.0012(11) C9 0.0215(16) 0.0256(17) 0.0263(17) 0.0017(13) 0.0088(13) -0.0001(13) C10 0.0282(18) 0.0266(18) 0.0245(17) 0.0028(13) 0.0061(14) 0.0020(13) C11 0.0228(17) 0.0272(18) 0.0281(19) -0.0016(12) 0.0014(14) -0.0004(12) C12 0.0262(17) 0.0237(16) 0.0299(19) -0.0012(13) 0.0109(14) -0.0032(13) _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 I C8 2.079(4) . ? N1 N2 1.294(4) . ? N1 C1 1.377(5) . ? N2 N3 1.372(4) . ? N3 C6 1.360(5) . ? N3 C7 1.428(5) . ? C1 C6 1.401(5) . ? C1 C2 1.409(5) . ? C2 C3 1.382(5) . ? C2 H2A 0.9500 . ? C3 C4 1.423(5) . ? C3 H3A 0.9500 . ? C4 C5 1.378(5) . ? C4 H4A 0.9500 . ? C5 C6 1.402(5) . ? C5 H5A 0.9500 . ? C7 C8 1.396(5) . ? C7 C12 1.402(5) . ? C8 C9 1.398(5) . ? C9 C10 1.392(6) . ? C9 H9A 0.9500 . ? C10 C11 1.380(5) . ? C10 H10A 0.9500 . ? C11 C12 1.390(5) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? 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 N2 N1 C1 108.8(3) . . ? N1 N2 N3 108.8(3) . . ? C6 N3 N2 109.8(3) . . ? C6 N3 C7 128.3(3) . . ? N2 N3 C7 121.5(3) . . ? N1 C1 C6 108.2(3) . . ? N1 C1 C2 130.9(3) . . ? C6 C1 C2 120.8(3) . . ? C3 C2 C1 117.1(3) . . ? C3 C2 H2A 121.5 . . ? C1 C2 H2A 121.5 . . ? C2 C3 C4 121.5(3) . . ? C2 C3 H3A 119.2 . . ? C4 C3 H3A 119.2 . . ? C5 C4 C3 121.8(3) . . ? C5 C4 H4A 119.1 . . ? C3 C4 H4A 119.1 . . ? C4 C5 C6 116.6(3) . . ? C4 C5 H5A 121.7 . . ? C6 C5 H5A 121.7 . . ? N3 C6 C1 104.3(3) . . ? N3 C6 C5 133.5(3) . . ? C1 C6 C5 122.2(3) . . ? C8 C7 C12 121.0(3) . . ? C8 C7 N3 121.1(3) . . ? C12 C7 N3 117.8(3) . . ? C7 C8 C9 118.6(3) . . ? C7 C8 I 121.8(3) . . ? C9 C8 I 119.6(3) . . ? C10 C9 C8 120.3(3) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C11 C10 C9 120.5(4) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C10 C11 C12 120.3(4) . . ? C10 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C11 C12 C7 119.2(3) . . ? C11 C12 H12A 120.4 . . ? C7 C12 H12A 120.4 . . ? 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 C1 N1 N2 N3 -0.5(4) . . . . ? N1 N2 N3 C6 0.4(4) . . . . ? N1 N2 N3 C7 173.9(3) . . . . ? N2 N1 C1 C6 0.5(4) . . . . ? N2 N1 C1 C2 -176.8(3) . . . . ? N1 C1 C2 C3 178.3(3) . . . . ? C6 C1 C2 C3 1.2(5) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C2 C3 C4 C5 -1.5(5) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? N2 N3 C6 C1 -0.1(4) . . . . ? C7 N3 C6 C1 -173.0(3) . . . . ? N2 N3 C6 C5 179.0(4) . . . . ? C7 N3 C6 C5 6.1(6) . . . . ? N1 C1 C6 N3 -0.2(4) . . . . ? C2 C1 C6 N3 177.4(3) . . . . ? N1 C1 C6 C5 -179.4(3) . . . . ? C2 C1 C6 C5 -1.8(5) . . . . ? C4 C5 C6 N3 -178.3(4) . . . . ? C4 C5 C6 C1 0.6(5) . . . . ? C6 N3 C7 C8 -87.5(5) . . . . ? N2 N3 C7 C8 100.3(4) . . . . ? C6 N3 C7 C12 92.8(4) . . . . ? N2 N3 C7 C12 -79.3(4) . . . . ? C12 C7 C8 C9 -0.3(5) . . . . ? N3 C7 C8 C9 -180.0(3) . . . . ? C12 C7 C8 I 177.9(3) . . . . ? N3 C7 C8 I -1.7(4) . . . . ? C7 C8 C9 C10 -0.1(5) . . . . ? I C8 C9 C10 -178.4(3) . . . . ? C8 C9 C10 C11 0.3(6) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C10 C11 C12 C7 -0.4(5) . . . . ? C8 C7 C12 C11 0.6(5) . . . . ? N3 C7 C12 C11 -179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.418 _refine_diff_density_min -1.139 _refine_diff_density_rms 0.145 data_cm09-2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N4 O2' _chemical_formula_sum 'C12 H8 N4 O2' _chemical_formula_weight 240.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 12.1674(3) _cell_length_b 6.98587(15) _cell_length_c 12.7296(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.201(3) _cell_angle_gamma 90.00 _cell_volume 1033.62(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2891 _cell_measurement_theta_min 5.9839 _cell_measurement_theta_max 74.1637 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.923 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78986 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 3656 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 7.15 _diffrn_reflns_theta_max 74.46 _reflns_number_total 2042 _reflns_number_gt 1849 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0715P)^2^+0.2442P] 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 2042 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 O1 O 0.87428(8) 0.55483(17) 0.70247(8) 0.0374(3) Uani 1 1 d . . . O2 O 0.97246(8) 0.57063(15) 0.87425(8) 0.0338(3) Uani 1 1 d . . . N1 N 0.36750(9) 0.67897(16) 0.51524(8) 0.0239(3) Uani 1 1 d . . . N2 N 0.47092(9) 0.67093(15) 0.58162(8) 0.0221(3) Uani 1 1 d . . . N3 N 0.46595(8) 0.63520(14) 0.68633(8) 0.0183(2) Uani 1 1 d . . . N4 N 0.88141(9) 0.57233(15) 0.80004(9) 0.0246(3) Uani 1 1 d . . . C1 C 0.29085(10) 0.65016(17) 0.57509(10) 0.0205(3) Uani 1 1 d . . . C2 C 0.17036(11) 0.64805(18) 0.53979(11) 0.0250(3) Uani 1 1 d . . . H2A H 0.1282 0.6687 0.4650 0.030 Uiso 1 1 calc R . . C3 C 0.11601(11) 0.61453(18) 0.61883(11) 0.0265(3) Uani 1 1 d . . . H3A H 0.0343 0.6124 0.5982 0.032 Uiso 1 1 calc R . . C4 C 0.17920(11) 0.58328(18) 0.72986(11) 0.0255(3) Uani 1 1 d . . . H4A H 0.1385 0.5598 0.7818 0.031 Uiso 1 1 calc R . . C5 C 0.29769(11) 0.58560(17) 0.76574(10) 0.0221(3) Uani 1 1 d . . . H5A H 0.3395 0.5641 0.8406 0.026 Uiso 1 1 calc R . . C6 C 0.35305(10) 0.62154(16) 0.68542(10) 0.0188(3) Uani 1 1 d . . . C7 C 0.57091(10) 0.62946(16) 0.77296(9) 0.0179(3) Uani 1 1 d . . . C8 C 0.67158(10) 0.58703(16) 0.74653(9) 0.0190(3) Uani 1 1 d . . . H8A H 0.6695 0.5506 0.6741 0.023 Uiso 1 1 calc R . . C9 C 0.77448(10) 0.59987(16) 0.82965(10) 0.0204(3) Uani 1 1 d . . . C10 C 0.78183(10) 0.64268(17) 0.93787(10) 0.0224(3) Uani 1 1 d . . . H10A H 0.8539 0.6470 0.9934 0.027 Uiso 1 1 calc R . . C11 C 0.67942(11) 0.67898(17) 0.96185(10) 0.0222(3) Uani 1 1 d . . . H11A H 0.6815 0.7063 1.0355 0.027 Uiso 1 1 calc R . . C12 C 0.57433(10) 0.67609(17) 0.88048(10) 0.0204(3) Uani 1 1 d . . . H12A H 0.5054 0.7055 0.8978 0.025 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0240(5) 0.0646(7) 0.0272(5) -0.0077(5) 0.0132(4) -0.0026(4) O2 0.0164(4) 0.0508(6) 0.0328(5) 0.0018(4) 0.0051(4) -0.0017(4) N1 0.0224(5) 0.0302(6) 0.0198(5) 0.0011(4) 0.0073(4) 0.0029(4) N2 0.0228(5) 0.0285(5) 0.0175(5) 0.0017(4) 0.0096(4) 0.0015(4) N3 0.0187(5) 0.0221(5) 0.0163(5) 0.0001(4) 0.0083(4) 0.0003(4) N4 0.0194(5) 0.0284(6) 0.0273(5) 0.0001(4) 0.0089(4) -0.0029(4) C1 0.0209(6) 0.0209(6) 0.0207(6) -0.0017(4) 0.0078(5) 0.0023(4) C2 0.0221(6) 0.0251(6) 0.0261(6) -0.0023(5) 0.0048(5) 0.0028(5) C3 0.0184(6) 0.0265(6) 0.0354(7) -0.0057(5) 0.0093(5) 0.0000(5) C4 0.0225(6) 0.0271(6) 0.0317(7) -0.0038(5) 0.0156(5) -0.0023(5) C5 0.0229(6) 0.0242(6) 0.0219(6) -0.0019(5) 0.0109(5) -0.0020(5) C6 0.0180(6) 0.0179(5) 0.0217(6) -0.0022(4) 0.0078(4) 0.0004(4) C7 0.0185(6) 0.0169(5) 0.0197(6) 0.0012(4) 0.0077(4) -0.0011(4) C8 0.0203(6) 0.0195(5) 0.0197(5) 0.0004(4) 0.0100(4) -0.0012(4) C9 0.0189(6) 0.0201(5) 0.0241(6) 0.0015(4) 0.0093(5) -0.0010(4) C10 0.0214(6) 0.0232(6) 0.0218(6) 0.0007(4) 0.0051(5) -0.0018(4) C11 0.0262(6) 0.0241(6) 0.0176(6) -0.0010(4) 0.0082(5) -0.0016(5) C12 0.0217(6) 0.0207(5) 0.0216(6) 0.0000(4) 0.0106(5) -0.0001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N4 1.2253(15) . ? O2 N4 1.2251(14) . ? N1 N2 1.2929(15) . ? N1 C1 1.3824(15) . ? N2 N3 1.3750(13) . ? N3 C6 1.3736(15) . ? N3 C7 1.4198(15) . ? N4 C9 1.4702(15) . ? C1 C6 1.3988(16) . ? C1 C2 1.4006(17) . ? C2 C3 1.3777(18) . ? C2 H2A 0.9500 . ? C3 C4 1.4119(19) . ? C3 H3A 0.9500 . ? C4 C5 1.3777(17) . ? C4 H4A 0.9500 . ? C5 C6 1.4033(16) . ? C5 H5A 0.9500 . ? C7 C8 1.3948(16) . ? C7 C12 1.3955(16) . ? C8 C9 1.3826(16) . ? C8 H8A 0.9500 . ? C9 C10 1.3865(17) . ? C10 C11 1.3911(17) . ? C10 H10A 0.9500 . ? C11 C12 1.3873(17) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? 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 N2 N1 C1 108.56(10) . . ? N1 N2 N3 109.16(9) . . ? C6 N3 N2 109.57(9) . . ? C6 N3 C7 132.24(10) . . ? N2 N3 C7 118.08(9) . . ? O2 N4 O1 123.87(11) . . ? O2 N4 C9 118.08(10) . . ? O1 N4 C9 118.04(10) . . ? N1 C1 C6 108.74(10) . . ? N1 C1 C2 129.61(11) . . ? C6 C1 C2 121.65(11) . . ? C3 C2 C1 116.78(12) . . ? C3 C2 H2A 121.6 . . ? C1 C2 H2A 121.6 . . ? C2 C3 C4 121.35(11) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 122.47(11) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? C4 C5 C6 116.18(11) . . ? C4 C5 H5A 121.9 . . ? C6 C5 H5A 121.9 . . ? N3 C6 C1 103.97(10) . . ? N3 C6 C5 134.47(11) . . ? C1 C6 C5 121.56(11) . . ? C8 C7 C12 120.84(11) . . ? C8 C7 N3 118.11(10) . . ? C12 C7 N3 120.95(10) . . ? C9 C8 C7 117.56(11) . . ? C9 C8 H8A 121.2 . . ? C7 C8 H8A 121.2 . . ? C8 C9 C10 123.51(11) . . ? C8 C9 N4 117.71(10) . . ? C10 C9 N4 118.75(11) . . ? C9 C10 C11 117.30(11) . . ? C9 C10 H10A 121.4 . . ? C11 C10 H10A 121.4 . . ? C12 C11 C10 121.41(11) . . ? C12 C11 H11A 119.3 . . ? C10 C11 H11A 119.3 . . ? C11 C12 C7 119.29(11) . . ? C11 C12 H12A 120.4 . . ? C7 C12 H12A 120.4 . . ? 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 C1 N1 N2 N3 0.52(13) . . . . ? N1 N2 N3 C6 -0.46(13) . . . . ? N1 N2 N3 C7 -177.22(9) . . . . ? N2 N1 C1 C6 -0.40(13) . . . . ? N2 N1 C1 C2 179.29(12) . . . . ? N1 C1 C2 C3 179.72(12) . . . . ? C6 C1 C2 C3 -0.62(18) . . . . ? C1 C2 C3 C4 -0.21(18) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? C3 C4 C5 C6 0.16(18) . . . . ? N2 N3 C6 C1 0.20(13) . . . . ? C7 N3 C6 C1 176.33(11) . . . . ? N2 N3 C6 C5 179.15(13) . . . . ? C7 N3 C6 C5 -4.7(2) . . . . ? N1 C1 C6 N3 0.11(13) . . . . ? C2 C1 C6 N3 -179.61(11) . . . . ? N1 C1 C6 C5 -179.01(11) . . . . ? C2 C1 C6 C5 1.27(18) . . . . ? C4 C5 C6 N3 -179.80(12) . . . . ? C4 C5 C6 C1 -0.99(17) . . . . ? C6 N3 C7 C8 160.08(12) . . . . ? N2 N3 C7 C8 -24.06(15) . . . . ? C6 N3 C7 C12 -23.68(18) . . . . ? N2 N3 C7 C12 152.19(11) . . . . ? C12 C7 C8 C9 -2.33(17) . . . . ? N3 C7 C8 C9 173.92(10) . . . . ? C7 C8 C9 C10 3.43(17) . . . . ? C7 C8 C9 N4 -174.59(10) . . . . ? O2 N4 C9 C8 -175.16(11) . . . . ? O1 N4 C9 C8 5.73(17) . . . . ? O2 N4 C9 C10 6.72(17) . . . . ? O1 N4 C9 C10 -172.38(12) . . . . ? C8 C9 C10 C11 -1.70(18) . . . . ? N4 C9 C10 C11 176.30(10) . . . . ? C9 C10 C11 C12 -1.19(18) . . . . ? C10 C11 C12 C7 2.19(18) . . . . ? C8 C7 C12 C11 -0.36(17) . . . . ? N3 C7 C12 C11 -176.50(10) . . . . ? 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 C4 H4A O2 0.95 2.62 3.5282(15) 159.5 1_455 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.243 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.048