# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Jane Hanrahan' _publ_contact_author_address ; Faculty of Pharmacy University of Sydney Sydney NSw 2042 AUSTRALIA ; _publ_contact_author_email JANEH@PHARM.USYD.EDU.AU _publ_section_title ; Studies on Pyridazine Azide Cyclisation Reactions ; loop_ _publ_author_name 'Jane Hanrahan' 'Robin D. Allan' 'Jeremy Greenwood' 'Trevor Hambley' 'Jane R. Hanraham' ; D. .E.Hibbs ; 'Samia Itani' 'Hue W. Tran' 'Peter Turner' data_6 _database_code_depnum_ccdc_archive 'CCDC 227308' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-diazido-4-methyl[1,5-b]tetrazolopridazine ; _chemical_name_common 3,5-diazido-4-methyl(1,5-b)tetrazolopridazine _chemical_melting_point 131-132oC _chemical_formula_moiety 'C5 H3 N11' _chemical_formula_sum 'C5 H3 N11' _chemical_formula_weight 217.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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 0.0030 0.0019 '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 8.124(4) _cell_length_b 16.606(10) _cell_length_c 7.179(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.24(2) _cell_angle_gamma 90.00 _cell_volume 889.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1478 _cell_measurement_theta_min 2 _cell_measurement_theta_max 19 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.015 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.075 _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 123(2) _diffrn_radiation_wavelength 0.56356 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Argonne National Lab, APS, ChemMatCARS' _diffrn_radiation_monochromator 'Double Diamond 111' _diffrn_measurement_device_type 'Bruker Kappa with 4 chip CCD' _diffrn_measurement_method \f _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1478 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 19.60 _reflns_number_total 1478 _reflns_number_gt 1049 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.03(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1478 _refine_ls_number_parameters 147 _refine_ls_number_restraints 96 _refine_ls_R_factor_all 0.2443 _refine_ls_R_factor_gt 0.2088 _refine_ls_wR_factor_ref 0.5585 _refine_ls_wR_factor_gt 0.5283 _refine_ls_goodness_of_fit_ref 2.339 _refine_ls_restrained_S_all 2.409 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.3024(13) 0.4834(6) 0.5508(16) 0.064(3) Uani 1 1 d U . . C2 C 0.2795(10) 0.4052(5) 0.4903(13) 0.052(2) Uani 1 1 d U . . C3 C 0.1283(14) 0.3831(7) 0.3235(16) 0.071(3) Uani 1 1 d U . . C4 C 0.0043(14) 0.4586(8) 0.2317(16) 0.077(3) Uani 1 1 d U . . C5 C 0.4123(13) 0.3390(6) 0.6044(15) 0.063(3) Uani 1 1 d U . . H4A H 0.5290 0.3622 0.6738 0.095 Uiso 1 1 calc R . . H4B H 0.4174 0.2992 0.5097 0.095 Uiso 1 1 calc R . . H4C H 0.3738 0.3142 0.7011 0.095 Uiso 1 1 calc R . . N1 N -0.1410(15) 0.4602(7) 0.0765(17) 0.094(3) Uani 1 1 d U . . N2 N -0.1726(14) 0.5456(6) 0.0826(16) 0.081(3) Uani 1 1 d U . . N3 N -0.0673(14) 0.5865(8) 0.2076(18) 0.089(3) Uani 1 1 d U . . N4 N 0.0652(15) 0.5270(6) 0.3235(17) 0.083(3) Uani 1 1 d U . . N5 N 0.2001(14) 0.5471(6) 0.4743(19) 0.088(3) Uani 1 1 d U . . N6 N 0.4552(11) 0.5029(5) 0.7223(14) 0.068(2) Uani 1 1 d U . . N7 N 0.4628(11) 0.5760(6) 0.7857(14) 0.075(3) Uani 1 1 d U . . N8 N 0.4874(14) 0.6388(7) 0.8612(16) 0.087(3) Uani 1 1 d U . . N9 N 0.0995(12) 0.3042(6) 0.2642(13) 0.075(3) Uani 1 1 d U . . N10 N -0.0451(15) 0.2865(8) 0.1085(17) 0.092(3) Uani 1 1 d U . . N11 N -0.1657(15) 0.2608(8) -0.0225(16) 0.096(3) Uani 1 1 d U . . 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 0.065(5) 0.071(5) 0.065(5) 0.010(4) 0.035(4) 0.011(4) C2 0.052(4) 0.054(4) 0.053(4) 0.001(3) 0.022(4) -0.002(3) C3 0.074(5) 0.085(6) 0.063(5) 0.011(4) 0.039(4) 0.017(4) C4 0.060(5) 0.122(7) 0.054(5) 0.020(5) 0.028(4) 0.005(5) C5 0.063(5) 0.060(5) 0.059(5) 0.002(4) 0.016(4) 0.009(4) N1 0.098(6) 0.097(6) 0.093(6) -0.010(5) 0.045(5) -0.008(5) N2 0.096(5) 0.074(5) 0.089(5) 0.003(4) 0.055(5) 0.015(4) N3 0.083(5) 0.120(7) 0.079(5) 0.024(5) 0.047(4) 0.019(5) N4 0.102(6) 0.079(5) 0.084(5) 0.016(4) 0.052(5) 0.016(4) N5 0.088(5) 0.083(6) 0.103(6) 0.011(5) 0.049(5) 0.005(4) N6 0.076(5) 0.062(4) 0.078(5) -0.006(4) 0.042(4) -0.002(3) N7 0.087(5) 0.064(5) 0.085(5) 0.000(4) 0.045(4) -0.007(4) N8 0.094(5) 0.084(6) 0.084(5) -0.004(4) 0.038(5) -0.002(4) N9 0.070(4) 0.085(5) 0.062(4) -0.004(4) 0.019(4) -0.001(4) N10 0.091(6) 0.113(7) 0.076(5) 0.002(5) 0.037(5) 0.002(5) N11 0.096(6) 0.101(6) 0.080(5) -0.006(5) 0.024(5) -0.007(5) _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 N5 1.323(14) . ? C1 C2 1.358(14) . ? C1 N6 1.398(13) . ? C2 C3 1.385(14) . ? C2 C5 1.531(13) . ? C3 N9 1.368(15) . ? C3 C4 1.581(16) . ? C4 N1 1.264(14) . ? C4 N4 1.308(16) . ? N1 N2 1.444(15) . ? N2 N3 1.181(14) . ? N3 N4 1.456(14) . ? N4 N5 1.244(15) . ? N6 N7 1.290(13) . ? N7 N8 1.156(14) . ? N9 N10 1.296(15) . ? N10 N11 1.140(14) . ? 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 N5 C1 C2 130.3(11) . . ? N5 C1 N6 112.0(10) . . ? C2 C1 N6 117.7(8) . . ? C1 C2 C3 119.5(9) . . ? C1 C2 C5 122.4(8) . . ? C3 C2 C5 118.0(8) . . ? N9 C3 C2 120.5(9) . . ? N9 C3 C4 128.9(10) . . ? C2 C3 C4 110.6(10) . . ? N1 C4 N4 117.5(12) . . ? N1 C4 C3 127.1(12) . . ? N4 C4 C3 115.3(10) . . ? C4 N1 N2 96.3(10) . . ? N3 N2 N1 120.2(11) . . ? N2 N3 N4 101.2(12) . . ? N5 N4 C4 134.3(11) . . ? N5 N4 N3 121.0(11) . . ? C4 N4 N3 104.7(11) . . ? N4 N5 C1 109.9(11) . . ? N7 N6 C1 115.5(9) . . ? N8 N7 N6 172.1(12) . . ? N10 N9 C3 118.1(9) . . ? N11 N10 N9 171.2(13) . . ? 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 N5 C1 C2 C3 -0.3(15) . . . . ? N6 C1 C2 C3 178.8(8) . . . . ? N5 C1 C2 C5 -178.1(9) . . . . ? N6 C1 C2 C5 1.0(12) . . . . ? C1 C2 C3 N9 -177.7(9) . . . . ? C5 C2 C3 N9 0.2(13) . . . . ? C1 C2 C3 C4 -0.2(12) . . . . ? C5 C2 C3 C4 177.7(7) . . . . ? N9 C3 C4 N1 -4.9(17) . . . . ? C2 C3 C4 N1 177.9(10) . . . . ? N9 C3 C4 N4 178.4(10) . . . . ? C2 C3 C4 N4 1.2(12) . . . . ? N4 C4 N1 N2 -1.7(11) . . . . ? C3 C4 N1 N2 -178.3(9) . . . . ? C4 N1 N2 N3 2.4(12) . . . . ? N1 N2 N3 N4 -2.0(11) . . . . ? N1 C4 N4 N5 -179.3(12) . . . . ? C3 C4 N4 N5 -2.3(17) . . . . ? N1 C4 N4 N3 0.8(12) . . . . ? C3 C4 N4 N3 177.8(7) . . . . ? N2 N3 N4 N5 -179.1(10) . . . . ? N2 N3 N4 C4 0.8(10) . . . . ? C4 N4 N5 C1 1.7(17) . . . . ? N3 N4 N5 C1 -178.4(8) . . . . ? C2 C1 N5 N4 -0.3(15) . . . . ? N6 C1 N5 N4 -179.4(9) . . . . ? N5 C1 N6 N7 5.7(12) . . . . ? C2 C1 N6 N7 -173.6(8) . . . . ? C1 N6 N7 N8 174(7) . . . . ? C2 C3 N9 N10 179.2(9) . . . . ? C4 C3 N9 N10 2.3(15) . . . . ? C3 N9 N10 N11 -174(7) . . . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 19.60 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 1.628 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.178 data_rda2 _database_code_depnum_ccdc_archive 'CCDC 231327' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H5 N9' _chemical_formula_weight 191.18 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7327(8) _cell_length_b 7.6069(6) _cell_length_c 10.450(2) _cell_angle_alpha 96.967(13) _cell_angle_beta 104.847(14) _cell_angle_gamma 109.680(8) _cell_volume 403.83(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 46.2 _cell_measurement_theta_max 52.1 _exptl_crystal_description columnar _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.125 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.995 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; psi scan (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.94 _exptl_special_details ; The scan width was (1.84+0.35tan\q)\% with an \w scan speed of 0\% per minute (up to 11 scans to achieve I/\s(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -9.44 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -2 1 2 -2 0 0 -2 0 _diffrn_reflns_number 1562 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.50 _diffrn_reflns_theta_max 67.64 _reflns_number_total 1444 _reflns_number_gt 1029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution ; SIR97 (Altomare, et. al. 1998) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan (MSC, 1992-1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.03P)^2^+0.2P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1444 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.284 _refine_ls_restrained_S_all 1.284 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.2999(5) 0.7598(3) 0.4378(3) 0.0611(7) Uani 1 1 d . . . N2 N 1.2778(5) 0.5751(3) 0.4294(3) 0.0702(8) Uani 1 1 d . . . N3 N 1.0456(5) 0.4551(3) 0.3525(3) 0.0651(8) Uani 1 1 d . . . N4 N 0.9131(4) 0.5643(3) 0.3079(3) 0.0527(6) Uani 1 1 d . . . N5 N 0.6648(4) 0.4896(3) 0.2259(3) 0.0567(7) Uani 1 1 d . . . N6 N 0.3171(5) 0.5635(3) 0.1138(3) 0.0675(8) Uani 1 1 d . . . N7 N 0.2030(5) 0.3842(4) 0.0791(3) 0.0703(8) Uani 1 1 d . . . N8 N 0.0781(6) 0.2280(4) 0.0407(4) 0.0956(11) Uani 1 1 d . . . N9 N 1.1327(4) 1.0780(3) 0.3753(3) 0.0584(7) Uani 1 1 d . . . H9NA H 1.0783 1.1669 0.3558 0.070 Uiso 1 1 calc R . . H9NB H 1.2900 1.1074 0.4269 0.070 Uiso 1 1 calc R . . C1 C 0.5778(5) 0.6246(4) 0.1976(3) 0.0526(7) Uani 1 1 d . . . C2 C 0.7179(5) 0.8273(3) 0.2419(3) 0.0505(7) Uani 1 1 d . . . C3 C 0.9720(5) 0.8931(3) 0.3250(3) 0.0479(7) Uani 1 1 d . . . C4 C 1.0720(5) 0.7508(3) 0.3608(3) 0.0493(7) Uani 1 1 d . . . C5 C 0.5914(6) 0.9635(4) 0.1981(4) 0.0666(9) Uani 1 1 d . . . H5A H 0.6113 1.0538 0.2767 0.100 Uiso 1 1 calc R . . H5B H 0.4089 0.8928 0.1503 0.100 Uiso 1 1 calc R . . H5C H 0.6731 1.0310 0.1393 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 N1 0.0525(14) 0.0335(11) 0.0895(19) 0.0136(11) 0.0076(13) 0.0184(10) N2 0.0647(17) 0.0365(13) 0.107(2) 0.0176(13) 0.0140(16) 0.0262(12) N3 0.0597(16) 0.0309(12) 0.100(2) 0.0134(12) 0.0129(15) 0.0219(11) N4 0.0494(13) 0.0248(10) 0.0753(17) 0.0083(10) 0.0101(12) 0.0121(9) N5 0.0516(14) 0.0293(11) 0.0756(17) 0.0048(11) 0.0086(12) 0.0100(10) N6 0.0559(15) 0.0343(13) 0.0840(19) 0.0057(12) -0.0019(14) 0.0036(11) N7 0.0556(16) 0.0490(16) 0.0780(19) 0.0027(13) -0.0006(14) 0.0058(13) N8 0.073(2) 0.0464(17) 0.122(3) -0.0050(16) 0.0013(19) -0.0017(15) N9 0.0471(13) 0.0253(11) 0.0877(18) 0.0083(11) 0.0028(12) 0.0107(10) C1 0.0456(15) 0.0360(14) 0.0632(18) 0.0074(12) 0.0060(13) 0.0095(11) C2 0.0468(16) 0.0302(13) 0.0646(18) 0.0091(12) 0.0083(14) 0.0103(11) C3 0.0456(15) 0.0268(12) 0.0652(18) 0.0091(11) 0.0123(13) 0.0107(11) C4 0.0439(15) 0.0280(12) 0.0669(18) 0.0071(12) 0.0089(13) 0.0103(11) C5 0.0538(18) 0.0397(15) 0.094(2) 0.0187(15) 0.0047(17) 0.0155(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 N1 C4 1.322(4) . ? N1 N2 1.357(3) . ? N2 N3 1.307(3) . ? N3 N4 1.350(3) . ? N4 N5 1.340(3) . ? N4 C4 1.352(3) . ? N5 C1 1.317(3) . ? N6 N7 1.256(3) . ? N6 C1 1.407(4) . ? N7 N8 1.118(4) . ? N9 C3 1.343(3) . ? N9 H9NA 0.8600 . ? N9 H9NB 0.8600 . ? C1 C2 1.428(4) . ? C2 C3 1.372(4) . ? C2 C5 1.504(4) . ? C3 C4 1.430(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 C4 N1 N2 105.6(2) . . ? N3 N2 N1 111.5(2) . . ? N2 N3 N4 105.8(2) . . ? N5 N4 N3 122.7(2) . . ? N5 N4 C4 128.8(2) . . ? N3 N4 C4 108.5(2) . . ? C1 N5 N4 111.4(2) . . ? N7 N6 C1 113.0(2) . . ? N8 N7 N6 172.4(4) . . ? C3 N9 H9NA 120.0 . . ? C3 N9 H9NB 120.0 . . ? H9NA N9 H9NB 120.0 . . ? N5 C1 N6 116.7(2) . . ? N5 C1 C2 127.5(3) . . ? N6 C1 C2 115.8(2) . . ? C3 C2 C1 117.7(2) . . ? C3 C2 C5 121.3(2) . . ? C1 C2 C5 121.0(3) . . ? N9 C3 C2 125.7(2) . . ? N9 C3 C4 117.8(2) . . ? C2 C3 C4 116.5(2) . . ? N1 C4 N4 108.6(2) . . ? N1 C4 C3 133.3(2) . . ? N4 C4 C3 118.0(2) . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 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 C4 N1 N2 N3 -1.0(4) . . . . ? N1 N2 N3 N4 0.8(4) . . . . ? N2 N3 N4 N5 -179.8(3) . . . . ? N2 N3 N4 C4 -0.3(3) . . . . ? N3 N4 N5 C1 179.4(3) . . . . ? C4 N4 N5 C1 0.0(4) . . . . ? C1 N6 N7 N8 180(100) . . . . ? N4 N5 C1 N6 -179.0(3) . . . . ? N4 N5 C1 C2 1.2(5) . . . . ? N7 N6 C1 N5 0.8(4) . . . . ? N7 N6 C1 C2 -179.3(3) . . . . ? N5 C1 C2 C3 -0.9(5) . . . . ? N6 C1 C2 C3 179.3(3) . . . . ? N5 C1 C2 C5 178.8(3) . . . . ? N6 C1 C2 C5 -1.1(5) . . . . ? C1 C2 C3 N9 179.5(3) . . . . ? C5 C2 C3 N9 -0.2(5) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C5 C2 C3 C4 179.7(3) . . . . ? N2 N1 C4 N4 0.8(4) . . . . ? N2 N1 C4 C3 -178.5(3) . . . . ? N5 N4 C4 N1 179.1(3) . . . . ? N3 N4 C4 N1 -0.3(4) . . . . ? N5 N4 C4 C3 -1.5(5) . . . . ? N3 N4 C4 C3 179.1(3) . . . . ? N9 C3 C4 N1 0.8(5) . . . . ? C2 C3 C4 N1 -179.1(3) . . . . ? N9 C3 C4 N4 -178.4(3) . . . . ? C2 C3 C4 N4 1.7(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 N9 H9NA N3 0.86 2.27 3.099(3) 163.3 1_565 N9 H9NB N1 0.86 2.21 3.062(3) 169.1 2_876 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 67.64 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.224 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.057