# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Sandeep Verma' _publ_contact_author_email SVERMA@IITK.AC.IN _publ_section_title ; Silver-catalyzed intramolecular cyclization of 9-propargyladenine via N3 alkylation ; loop_ _publ_author_name 'Sandeep Verma' 'Jitendra Kumar' 'Rajneesh Kumar Prajapati' # Attachment 'SV_merged_cif.cif' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 757808' #TrackingRef 'SV_merged_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N5' _chemical_formula_weight 173.19 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 4.232(2) _cell_length_b 8.030(5) _cell_length_c 23.829(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 809.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1548 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.99 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _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-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4220 _diffrn_reflns_av_R_equivalents 0.0672 _diffrn_reflns_av_sigmaI/netI 0.1916 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1548 _reflns_number_gt 1242 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _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^)+(0.0706P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -4(4) _refine_ls_number_reflns 1548 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1220 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C2 C 0.0027(6) 0.3050(3) 0.16676(9) 0.0493(6) Uani 1 1 d . . . H2 H -0.0576 0.4164 0.1657 0.059 Uiso 1 1 calc R . . C4 C -0.0193(5) 0.0523(3) 0.13255(8) 0.0401(5) Uani 1 1 d . . . C5 C 0.1808(5) -0.0092(3) 0.17307(8) 0.0385(5) Uani 1 1 d . . . C6 C 0.2959(5) 0.1056(3) 0.21261(8) 0.0400(5) Uani 1 1 d . . . C8 C 0.0582(6) -0.2135(3) 0.12121(10) 0.0470(6) Uani 1 1 d . . . H8 H 0.0432 -0.3201 0.1063 0.056 Uiso 1 1 calc R . . C9 C -0.2928(6) -0.0748(4) 0.04944(8) 0.0523(7) Uani 1 1 d . . . H9A H -0.4821 -0.0109 0.0574 0.063 Uiso 1 1 calc R . . H9B H -0.3567 -0.1871 0.0397 0.063 Uiso 1 1 calc R . . C10 C -0.1269(6) 0.0002(4) 0.00187(9) 0.0507(6) Uani 1 1 d . . . C11 C 0.0032(7) 0.0659(4) -0.03495(11) 0.0652(8) Uani 1 1 d . . . H11 H 0.1073 0.1184 -0.0644 0.078 Uiso 1 1 calc R . . N1 N 0.1988(5) 0.2639(3) 0.20812(7) 0.0451(5) Uani 1 1 d . . . N3 N -0.1191(5) 0.2091(3) 0.12680(8) 0.0486(6) Uani 1 1 d . . . N6 N 0.4927(5) 0.0672(3) 0.25399(7) 0.0490(5) Uani 1 1 d . . . H6A H 0.5544 0.1429 0.2770 0.059 Uiso 1 1 calc R . . H6B H 0.5584 -0.0336 0.2578 0.059 Uiso 1 1 calc R . . N7 N 0.2298(5) -0.1773(3) 0.16563(7) 0.0458(5) Uani 1 1 d . . . N9 N -0.0944(4) -0.0799(3) 0.09938(7) 0.0435(5) 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 C2 0.0577(15) 0.0405(15) 0.0497(13) 0.0051(11) -0.0008(12) 0.0051(12) C4 0.0419(11) 0.0414(15) 0.0369(10) 0.0043(9) 0.0044(9) -0.0043(11) C5 0.0423(11) 0.0359(13) 0.0372(10) 0.0027(10) 0.0034(9) -0.0002(10) C6 0.0450(11) 0.0364(15) 0.0387(10) 0.0023(10) 0.0036(10) -0.0032(10) C8 0.0566(13) 0.0412(15) 0.0432(12) -0.0013(11) 0.0010(11) -0.0072(12) C9 0.0519(13) 0.067(2) 0.0382(11) 0.0032(13) -0.0059(11) -0.0139(14) C10 0.0538(13) 0.0559(18) 0.0423(12) -0.0022(13) -0.0013(11) -0.0041(12) C11 0.0764(19) 0.067(2) 0.0518(14) 0.0095(14) 0.0082(14) -0.0068(17) N1 0.0514(11) 0.0397(13) 0.0442(10) 0.0000(9) -0.0019(9) 0.0012(9) N3 0.0527(12) 0.0469(14) 0.0463(10) 0.0036(10) -0.0031(9) 0.0049(9) N6 0.0652(12) 0.0340(12) 0.0478(10) -0.0001(8) -0.0151(9) -0.0023(11) N7 0.0552(12) 0.0393(13) 0.0429(10) 0.0008(9) -0.0025(9) -0.0017(9) N9 0.0482(11) 0.0441(13) 0.0384(9) 0.0012(9) -0.0005(8) -0.0062(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N3 1.329(3) . ? C2 N1 1.330(3) . ? C4 N3 1.335(3) . ? C4 N9 1.361(3) . ? C4 C5 1.376(3) . ? C5 N7 1.377(3) . ? C5 C6 1.405(3) . ? C6 N6 1.327(3) . ? C6 N1 1.340(3) . ? C8 N7 1.316(3) . ? C8 N9 1.356(3) . ? C9 N9 1.457(3) . ? C9 C10 1.463(3) . ? C10 C11 1.162(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C2 N1 129.0(3) . . ? N3 C4 N9 127.0(2) . . ? N3 C4 C5 127.3(2) . . ? N9 C4 C5 105.7(2) . . ? C4 C5 N7 110.7(2) . . ? C4 C5 C6 116.6(2) . . ? N7 C5 C6 132.6(2) . . ? N6 C6 N1 118.2(2) . . ? N6 C6 C5 124.3(2) . . ? N1 C6 C5 117.6(2) . . ? N7 C8 N9 113.4(2) . . ? N9 C9 C10 111.6(2) . . ? C11 C10 C9 177.3(3) . . ? C2 N1 C6 119.1(2) . . ? C2 N3 C4 110.5(2) . . ? C8 N7 C5 103.7(2) . . ? C8 N9 C4 106.43(18) . . ? C8 N9 C9 127.6(2) . . ? C4 N9 C9 125.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C4 C5 N7 179.9(2) . . . . ? N9 C4 C5 N7 -0.2(2) . . . . ? N3 C4 C5 C6 -0.6(3) . . . . ? N9 C4 C5 C6 179.28(18) . . . . ? C4 C5 C6 N6 -179.4(2) . . . . ? N7 C5 C6 N6 0.0(4) . . . . ? C4 C5 C6 N1 0.9(3) . . . . ? N7 C5 C6 N1 -179.8(2) . . . . ? N9 C9 C10 C11 -75(6) . . . . ? N3 C2 N1 C6 -0.2(4) . . . . ? N6 C6 N1 C2 179.70(18) . . . . ? C5 C6 N1 C2 -0.5(3) . . . . ? N1 C2 N3 C4 0.4(3) . . . . ? N9 C4 N3 C2 -179.9(2) . . . . ? C5 C4 N3 C2 0.0(3) . . . . ? N9 C8 N7 C5 0.6(3) . . . . ? C4 C5 N7 C8 -0.2(2) . . . . ? C6 C5 N7 C8 -179.6(2) . . . . ? N7 C8 N9 C4 -0.8(3) . . . . ? N7 C8 N9 C9 177.5(2) . . . . ? N3 C4 N9 C8 -179.5(2) . . . . ? C5 C4 N9 C8 0.6(2) . . . . ? N3 C4 N9 C9 2.1(3) . . . . ? C5 C4 N9 C9 -177.76(19) . . . . ? C10 C9 N9 C8 -103.3(3) . . . . ? C10 C9 N9 C4 74.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.240 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.079 data_complex2 _database_code_depnum_ccdc_archive 'CCDC 757809' #TrackingRef 'SV_merged_cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 N6 O3' _chemical_formula_weight 236.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.536(3) _cell_length_b 6.938(4) _cell_length_c 12.729(7) _cell_angle_alpha 93.040(10) _cell_angle_beta 97.088(10) _cell_angle_gamma 101.559(10) _cell_volume 473.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1643 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 25 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2428 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0879 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1643 _reflns_number_gt 1242 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _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^)+(0.1216P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.09(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1643 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1776 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 C2 C 0.2488(6) 0.6062(4) 1.1201(2) 0.0217(7) Uani 1 1 d . . . H2 H 0.0918 0.5272 1.1200 0.026 Uiso 1 1 calc R . . C4 C 0.6161(6) 0.7792(4) 1.2102(2) 0.0191(7) Uani 1 1 d . . . C5 C 0.7066(6) 0.8354(4) 1.1186(2) 0.0196(7) Uani 1 1 d . . . C6 C 0.5500(6) 0.7679(4) 1.0228(2) 0.0201(7) Uani 1 1 d . . . C8 C 0.9811(5) 0.9615(4) 1.2497(2) 0.0227(7) Uani 1 1 d . . . H8 H 1.1264 1.0319 1.2902 0.027 Uiso 1 1 calc R . . C9 C 0.7439(6) 0.8234(5) 1.4036(2) 0.0241(8) Uani 1 1 d . . . H9A H 0.7582 0.9492 1.4435 0.029 Uiso 1 1 calc R . . H9B H 0.8679 0.7573 1.4373 0.029 Uiso 1 1 calc R . . C10 C 0.4902(6) 0.7000(5) 1.4029(2) 0.0246(8) Uani 1 1 d . . . H10 H 0.4414 0.6724 1.4688 0.029 Uiso 1 1 calc R . . C11 C 0.3290(6) 0.6265(4) 1.3196(2) 0.0230(7) Uani 1 1 d . . . H11 H 0.1758 0.5490 1.3278 0.028 Uiso 1 1 calc R . . N1 N 0.3176(4) 0.6515(4) 1.02781(17) 0.0200(7) Uani 1 1 d . . . N2 N 0.2868(5) 0.7006(4) 0.67436(18) 0.0218(6) Uani 1 1 d . . . N3 N 0.3895(4) 0.6659(4) 1.21504(17) 0.0194(6) Uani 1 1 d . . . N6 N 0.6094(5) 0.8090(3) 0.92779(17) 0.0212(7) Uani 1 1 d . . . H6A H 0.5053 0.7639 0.8719 0.025 Uiso 1 1 calc R . . H6B H 0.7522 0.8808 0.9219 0.025 Uiso 1 1 calc R . . N7 N 0.9422(4) 0.9535(4) 1.14518(18) 0.0220(7) Uani 1 1 d . . . N9 N 0.7862(4) 0.8558(4) 1.29283(18) 0.0198(6) Uani 1 1 d . . . O1 O 0.2455(4) 0.6113(3) 0.75672(15) 0.0267(6) Uani 1 1 d . . . O2 O 0.1272(4) 0.6686(3) 0.59475(15) 0.0305(7) Uani 1 1 d . . . O3 O 0.4873(4) 0.8193(3) 0.67478(16) 0.0290(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0159(16) 0.0220(16) 0.0271(16) 0.0032(12) 0.0030(12) 0.0034(13) C4 0.0180(16) 0.0208(16) 0.0201(14) 0.0072(11) 0.0073(11) 0.0034(13) C5 0.0191(16) 0.0210(16) 0.0202(14) 0.0062(11) 0.0067(12) 0.0040(13) C6 0.0219(17) 0.0187(16) 0.0212(15) 0.0074(11) 0.0059(12) 0.0041(13) C8 0.0138(16) 0.0290(17) 0.0252(15) 0.0059(12) 0.0041(12) 0.0027(13) C9 0.0253(18) 0.0313(18) 0.0155(14) 0.0082(12) 0.0048(12) 0.0027(14) C10 0.0321(19) 0.0307(18) 0.0153(14) 0.0100(12) 0.0118(13) 0.0094(14) C11 0.0223(17) 0.0271(17) 0.0222(15) 0.0090(12) 0.0119(12) 0.0040(14) N1 0.0168(13) 0.0234(14) 0.0194(13) 0.0055(10) 0.0039(10) 0.0013(11) N2 0.0206(14) 0.0251(14) 0.0199(12) 0.0040(10) 0.0058(10) 0.0027(11) N3 0.0158(13) 0.0256(14) 0.0168(12) 0.0064(10) 0.0037(10) 0.0022(11) N6 0.0203(14) 0.0294(15) 0.0139(12) 0.0075(10) 0.0043(10) 0.0025(11) N7 0.0132(13) 0.0258(14) 0.0259(13) 0.0059(10) 0.0040(10) -0.0004(11) N9 0.0172(14) 0.0250(14) 0.0175(12) 0.0061(10) 0.0046(10) 0.0024(11) O1 0.0284(13) 0.0348(13) 0.0186(11) 0.0131(9) 0.0074(9) 0.0053(10) O2 0.0226(13) 0.0451(15) 0.0189(11) 0.0102(9) -0.0002(9) -0.0050(10) O3 0.0177(12) 0.0337(13) 0.0323(12) 0.0075(9) 0.0057(9) -0.0051(10) _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 C2 N1 1.314(3) . ? C2 N3 1.351(4) . ? C4 N9 1.330(4) . ? C4 N3 1.351(4) . ? C4 C5 1.371(4) . ? C5 N7 1.386(4) . ? C5 C6 1.404(4) . ? C6 N6 1.323(3) . ? C6 N1 1.386(4) . ? C8 N7 1.318(4) . ? C8 N9 1.369(4) . ? C9 N9 1.479(3) . ? C9 C10 1.490(4) . ? C10 C11 1.307(4) . ? C11 N3 1.439(3) . ? N2 O2 1.238(3) . ? N2 O3 1.241(3) . ? N2 O1 1.268(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 N3 124.8(3) . . ? N9 C4 N3 125.9(3) . . ? N9 C4 C5 109.0(3) . . ? N3 C4 C5 125.1(3) . . ? C4 C5 N7 108.5(3) . . ? C4 C5 C6 116.8(3) . . ? N7 C5 C6 134.7(3) . . ? N6 C6 N1 117.7(3) . . ? N6 C6 C5 124.2(3) . . ? N1 C6 C5 118.1(2) . . ? N7 C8 N9 113.3(3) . . ? N9 C9 C10 108.9(2) . . ? C11 C10 C9 126.9(3) . . ? C10 C11 N3 119.8(3) . . ? C2 N1 C6 120.3(2) . . ? O2 N2 O3 120.9(2) . . ? O2 N2 O1 119.7(2) . . ? O3 N2 O1 119.4(2) . . ? C2 N3 C4 115.0(2) . . ? C2 N3 C11 128.7(3) . . ? C4 N3 C11 116.3(2) . . ? C8 N7 C5 104.1(2) . . ? C4 N9 C8 105.1(2) . . ? C4 N9 C9 122.2(2) . . ? C8 N9 C9 132.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N9 C4 C5 N7 -0.6(4) . . . . ? N3 C4 C5 N7 178.8(3) . . . . ? N9 C4 C5 C6 -179.8(2) . . . . ? N3 C4 C5 C6 -0.4(5) . . . . ? C4 C5 C6 N6 180.0(3) . . . . ? N7 C5 C6 N6 1.0(6) . . . . ? C4 C5 C6 N1 0.3(4) . . . . ? N7 C5 C6 N1 -178.7(3) . . . . ? N9 C9 C10 C11 1.4(5) . . . . ? C9 C10 C11 N3 -1.1(5) . . . . ? N3 C2 N1 C6 0.3(5) . . . . ? N6 C6 N1 C2 -180.0(3) . . . . ? C5 C6 N1 C2 -0.3(4) . . . . ? N1 C2 N3 C4 -0.4(5) . . . . ? N1 C2 N3 C11 179.0(3) . . . . ? N9 C4 N3 C2 179.7(3) . . . . ? C5 C4 N3 C2 0.4(5) . . . . ? N9 C4 N3 C11 0.2(5) . . . . ? C5 C4 N3 C11 -179.0(3) . . . . ? C10 C11 N3 C2 -179.1(3) . . . . ? C10 C11 N3 C4 0.2(4) . . . . ? N9 C8 N7 C5 0.2(3) . . . . ? C4 C5 N7 C8 0.2(3) . . . . ? C6 C5 N7 C8 179.3(3) . . . . ? N3 C4 N9 C8 -178.8(3) . . . . ? C5 C4 N9 C8 0.6(3) . . . . ? N3 C4 N9 C9 0.1(5) . . . . ? C5 C4 N9 C9 179.5(3) . . . . ? N7 C8 N9 C4 -0.5(4) . . . . ? N7 C8 N9 C9 -179.2(3) . . . . ? C10 C9 N9 C4 -0.8(4) . . . . ? C10 C9 N9 C8 177.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.443 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.158