# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Jingsong You' _publ_contact_author_email JSYOU@SCU.EDU.CN _publ_section_title ; Pyrido[1,2-c][1,2,4]triazol-3-ylidene: Reactivity and Its Application in Organocatalysis and Organometallic Catalysis ; loop_ _publ_author_name 'Jingsong You' 'Jingbo Lan' 'Bo Liu' 'Zhen Wang' 'Siping Wei' 'Jie Wu' ; Dongbing Zhao ; # Data for compound 8 data_8 _database_code_depnum_ccdc_archive 'CCDC 725112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H11 N3 O' _chemical_formula_weight 165.20 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 9.825(4) _cell_length_b 10.199(4) _cell_length_c 10.461(4) _cell_angle_alpha 62.00(3) _cell_angle_beta 73.41(4) _cell_angle_gamma 83.80(4) _cell_volume 886.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.53 _cell_measurement_theta_max 7.25 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9649 _exptl_absorpt_correction_T_max 0.9780 _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 CAD-4 _diffrn_measurement_method Omega/2-Theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.269 _diffrn_reflns_number 3669 _diffrn_reflns_av_R_equivalents 0.0065 _diffrn_reflns_av_sigmaI/netI 0.0814 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.54 _reflns_number_total 3258 _reflns_number_gt 1362 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.032(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3258 _refine_ls_number_parameters 246 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1664 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.1114(2) 0.5597(2) 1.0795(2) 0.0561(6) Uani 1 d . . . N2 N 0.1892(2) 0.5062(2) 0.8836(2) 0.0621(6) Uani 1 d . . . HN2 H 0.087(3) 0.490(3) 0.895(3) 0.088(9) Uiso 1 d . . . N3 N 0.2841(2) 0.5327(2) 0.7465(2) 0.0552(6) Uani 1 d . . . C1 C 0.2199(3) 0.5642(3) 0.9675(3) 0.0485(6) Uani 1 d . . . C2 C 0.3548(3) 0.6177(3) 0.9418(3) 0.0585(7) Uani 1 d . . . H2 H 0.4288 0.6207 0.8617 0.070 Uiso 1 calc R . . C3 C 0.3756(3) 0.6652(3) 1.0362(3) 0.0699(8) Uani 1 d . . . H3 H 0.4647 0.7013 1.0214 0.084 Uiso 1 calc R . . C4 C 0.2653(4) 0.6600(3) 1.1532(3) 0.0731(8) Uani 1 d . . . H4 H 0.2779 0.6918 1.2192 0.088 Uiso 1 calc R . . C5 C 0.1361(3) 0.6069(3) 1.1704(3) 0.0673(8) Uani 1 d . . . H5 H 0.0610 0.6034 1.2500 0.081 Uiso 1 calc R . . C6 C 0.3590(3) 0.4180(5) 0.7373(4) 0.0666(8) Uani 0.50 d PU . . H6 H 0.320(6) 0.329(6) 0.870(6) 0.05(2) Uiso 0.50 d P . . O1 O 0.4520(5) 0.4076(8) 0.6460(7) 0.0804(15) Uani 0.50 d P . . C6' C 0.3590(3) 0.4180(5) 0.7373(4) 0.0666(8) Uani 0.50 d PU . . H6' H 0.429(7) 0.476(6) 0.615(8) 0.05(2) Uiso 0.50 d P . . O1' O 0.3530(6) 0.3007(6) 0.8192(7) 0.0807(14) Uani 0.50 d P . . C7 C 0.2905(3) 0.6794(3) 0.6184(3) 0.0665(8) Uani 1 d . . . H7A H 0.3590 0.6791 0.5308 0.080 Uiso 1 calc R . . H7B H 0.3239 0.7518 0.6389 0.080 Uiso 1 calc R . . C8 C 0.1508(3) 0.7256(3) 0.5835(3) 0.0809(9) Uani 1 d . . . H8A H 0.1180 0.6556 0.5609 0.121 Uiso 1 calc R . . H8B H 0.1614 0.8224 0.4985 0.121 Uiso 1 calc R . . H8C H 0.0830 0.7286 0.6688 0.121 Uiso 1 calc R . . N4 N 0.4394(2) 0.0122(2) 0.3401(2) 0.0570(6) Uani 1 d . . . N5 N 0.3584(2) 0.1447(3) 0.4699(3) 0.0624(7) Uani 1 d . . . HN5 H 0.419(3) 0.091(3) 0.530(3) 0.108(12) Uiso 1 d . . . N6 N 0.2417(2) 0.2019(3) 0.5372(2) 0.0599(6) Uani 1 d . . . C9 C 0.3447(3) 0.1064(3) 0.3642(3) 0.0512(6) Uani 1 d . . . C10 C 0.2433(3) 0.1687(3) 0.2844(3) 0.0616(7) Uani 1 d . . . H10 H 0.1796 0.2365 0.3022 0.074 Uiso 1 calc R . . C11 C 0.2404(3) 0.1267(3) 0.1791(3) 0.0699(8) Uani 1 d . . . H11 H 0.1738 0.1663 0.1239 0.084 Uiso 1 calc R . . C12 C 0.3346(3) 0.0271(3) 0.1539(3) 0.0698(8) Uani 1 d . . . H12 H 0.3324 -0.0031 0.0834 0.084 Uiso 1 calc R . . C13 C 0.4323(3) -0.0267(3) 0.2358(3) 0.0662(8) Uani 1 d . . . H13 H 0.4973 -0.0939 0.2185 0.079 Uiso 1 calc R . . C14 C 0.1254(3) 0.1014(3) 0.6530(3) 0.0763(9) Uani 1 d . . . H14A H 0.1028 0.0343 0.6197 0.092 Uiso 1 calc R . . H14B H 0.0421 0.1590 0.6658 0.092 Uiso 1 calc R . . C15 C 0.1577(4) 0.0124(4) 0.8008(4) 0.1152(13) Uani 1 d . . . H15A H 0.2415 -0.0433 0.7888 0.173 Uiso 1 calc R . . H15B H 0.0791 -0.0547 0.8707 0.173 Uiso 1 calc R . . H15C H 0.1735 0.0777 0.8381 0.173 Uiso 1 calc R . . C16 C 0.2463(3) 0.3449(3) 0.4999(3) 0.0671(8) Uani 1 d . . . H16 H 0.3262 0.4005 0.4274 0.081 Uiso 1 calc R . . O2 O 0.1554(2) 0.4093(2) 0.5523(3) 0.0969(7) Uani 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 N1 0.0489(14) 0.0696(14) 0.0504(12) -0.0332(12) -0.0013(11) -0.0062(11) N2 0.0429(14) 0.0926(17) 0.0545(13) -0.0430(13) 0.0031(11) -0.0117(13) N3 0.0417(13) 0.0689(15) 0.0473(13) -0.0270(12) -0.0001(10) 0.0011(11) C1 0.0444(16) 0.0521(15) 0.0466(14) -0.0212(13) -0.0108(13) -0.0005(12) C2 0.0420(17) 0.0721(19) 0.0579(16) -0.0269(15) -0.0116(13) -0.0034(14) C3 0.0583(19) 0.076(2) 0.0718(19) -0.0248(16) -0.0222(16) -0.0161(15) C4 0.088(2) 0.073(2) 0.0675(19) -0.0342(16) -0.0252(18) -0.0137(18) C5 0.070(2) 0.0754(19) 0.0603(17) -0.0386(16) -0.0068(15) -0.0051(16) C6 0.054(2) 0.083(2) 0.072(2) -0.044(2) -0.0174(18) 0.0051(19) O1 0.062(3) 0.111(5) 0.069(3) -0.055(4) -0.002(2) 0.018(3) C6' 0.054(2) 0.083(2) 0.072(2) -0.044(2) -0.0174(18) 0.0051(19) O1' 0.103(4) 0.068(3) 0.072(3) -0.031(3) -0.036(3) 0.023(3) C7 0.0531(18) 0.072(2) 0.0588(17) -0.0212(16) -0.0068(14) -0.0037(14) C8 0.062(2) 0.0681(19) 0.099(2) -0.0246(17) -0.0284(17) 0.0059(16) N4 0.0560(14) 0.0552(13) 0.0584(13) -0.0284(11) -0.0121(11) 0.0096(11) N5 0.0482(15) 0.0816(17) 0.0760(16) -0.0521(15) -0.0229(13) 0.0235(13) N6 0.0483(14) 0.0674(16) 0.0704(15) -0.0395(13) -0.0151(12) 0.0127(12) C9 0.0424(15) 0.0551(16) 0.0501(15) -0.0210(14) -0.0094(13) 0.0012(13) C10 0.0512(18) 0.0707(19) 0.0625(17) -0.0304(16) -0.0174(14) 0.0091(14) C11 0.065(2) 0.083(2) 0.0572(17) -0.0243(17) -0.0226(15) 0.0002(17) C12 0.080(2) 0.078(2) 0.0541(17) -0.0308(16) -0.0181(16) -0.0053(18) C13 0.075(2) 0.0617(18) 0.0587(17) -0.0305(15) -0.0093(16) 0.0056(16) C14 0.0540(19) 0.093(2) 0.078(2) -0.0401(18) -0.0105(16) 0.0004(17) C15 0.095(3) 0.131(3) 0.082(3) -0.019(2) -0.017(2) -0.013(2) C16 0.060(2) 0.079(2) 0.080(2) -0.0489(18) -0.0251(16) 0.0134(16) O2 0.0917(16) 0.1007(16) 0.1213(17) -0.0766(15) -0.0264(13) 0.0329(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 C1 1.326(3) . ? N1 C5 1.335(3) . ? N2 C1 1.374(3) . ? N2 N3 1.387(3) . ? N2 HN2 1.00(3) . ? N3 C6 1.341(4) . ? N3 C7 1.459(3) . ? C1 C2 1.393(3) . ? C2 C3 1.356(3) . ? C2 H2 0.9300 . ? C3 C4 1.367(4) . ? C3 H3 0.9300 . ? C4 C5 1.366(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 O1' 1.092(5) . ? C6 O1 1.155(5) . ? C6 H6 1.22(5) . ? C6 H6' 1.16(7) . ? O1 O1' 1.668(9) . ? O1 H6' 0.66(5) . ? O1' H6 0.71(5) . ? C7 C8 1.491(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? N4 C9 1.324(3) . ? N4 C13 1.344(3) . ? N5 C9 1.376(3) . ? N5 N6 1.390(3) . ? N5 HN5 0.93(3) . ? N6 C16 1.324(3) . ? N6 C14 1.456(3) . ? C9 C10 1.391(3) . ? C10 C11 1.364(3) . ? C10 H10 0.9300 . ? C11 C12 1.366(4) . ? C11 H11 0.9300 . ? C12 C13 1.368(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.488(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O2 1.209(3) . ? C16 H16 0.9300 . ? 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 N1 C5 117.3(2) . . ? C1 N2 N3 119.1(2) . . ? C1 N2 HN2 118.2(14) . . ? N3 N2 HN2 116.7(15) . . ? C6 N3 N2 117.6(2) . . ? C6 N3 C7 123.4(2) . . ? N2 N3 C7 118.9(2) . . ? N1 C1 N2 114.3(2) . . ? N1 C1 C2 122.5(2) . . ? N2 C1 C2 123.1(2) . . ? C3 C2 C1 118.4(3) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 118.1(3) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N1 C5 C4 123.7(3) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? O1' C6 O1 95.9(6) . . ? O1' C6 N3 130.5(4) . . ? O1 C6 N3 133.6(5) . . ? O1' C6 H6 35(2) . . ? O1 C6 H6 128(3) . . ? N3 C6 H6 97(2) . . ? O1' C6 H6' 129(3) . . ? O1 C6 H6' 33(3) . . ? N3 C6 H6' 101(3) . . ? H6 C6 H6' 160(4) . . ? C6 O1 O1' 40.6(4) . . ? C6 O1 H6' 74(7) . . ? O1' O1 H6' 114(7) . . ? C6 O1' O1 43.5(4) . . ? C6 O1' H6 82(5) . . ? O1 O1' H6 122(5) . . ? N3 C7 C8 113.1(2) . . ? N3 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N3 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 N4 C13 117.2(2) . . ? C9 N5 N6 118.4(2) . . ? C9 N5 HN5 119.2(18) . . ? N6 N5 HN5 114.9(18) . . ? C16 N6 N5 117.8(2) . . ? C16 N6 C14 122.8(2) . . ? N5 N6 C14 119.2(2) . . ? N4 C9 N5 114.8(2) . . ? N4 C9 C10 123.2(2) . . ? N5 C9 C10 121.9(2) . . ? C11 C10 C9 117.6(3) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 117.9(3) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 121.1 . . ? N4 C13 C12 123.5(3) . . ? N4 C13 H13 118.3 . . ? C12 C13 H13 118.3 . . ? N6 C14 C15 113.5(2) . . ? N6 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? N6 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2 C16 N6 125.5(3) . . ? O2 C16 H16 117.3 . . ? N6 C16 H16 117.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 HN2 N1 1.00(3) 1.98(3) 2.976(3) 176(2) 2_567 N5 HN5 N4 0.93(3) 2.08(3) 3.006(4) 176(3) 2_656 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.54 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.183 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.038 # Attachment 'CCDC_725113.CIF' # Data for compound 9 (CCDC 725113) data_CCDC_725113 _database_code_depnum_ccdc_archive 'CCDC 725113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 N3' _chemical_formula_weight 135.17 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/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 5.329(3) _cell_length_b 9.235(2) _cell_length_c 14.718(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.53(3) _cell_angle_gamma 90.00 _cell_volume 723.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 4.60 _cell_measurement_theta_max 9.29 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CAD4 _diffrn_measurement_method Omega/2-Theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 120 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.234 _diffrn_reflns_number 1408 _diffrn_reflns_av_R_equivalents 0.0048 _diffrn_reflns_av_sigmaI/netI 0.0812 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1288 _reflns_number_gt 471 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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 w=1/[\s^2^(Fo^2^)+(0.0671P)^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 0.023(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1288 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2079 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1692 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4832(5) 1.0456(3) 0.12446(18) 0.0583(9) Uani 1 d . . . N2 N 0.2306(5) 0.8796(3) 0.04803(19) 0.0627(9) Uani 1 d . . . HN2 H 0.3267 0.8858 0.0034 0.075 Uiso 1 calc R . . N3 N 0.0260(5) 0.7887(3) 0.04327(19) 0.0602(9) Uani 1 d . . . C1 C 0.2786(7) 0.9603(4) 0.1256(2) 0.0536(10) Uani 1 d . . . C2 C 0.1265(7) 0.9545(4) 0.1989(3) 0.0669(11) Uani 1 d . . . H2 H -0.0128 0.8937 0.1979 0.080 Uiso 1 calc R . . C3 C 0.1873(7) 1.0402(4) 0.2720(3) 0.0760(12) Uani 1 d . . . H3 H 0.0869 1.0390 0.3215 0.091 Uiso 1 calc R . . C4 C 0.3964(8) 1.1293(4) 0.2739(3) 0.0751(13) Uani 1 d . . . H4 H 0.4400 1.1887 0.3235 0.090 Uiso 1 calc R . . C5 C 0.5353(7) 1.1253(4) 0.1987(3) 0.0677(12) Uani 1 d . . . H5 H 0.6784 1.1830 0.1996 0.081 Uiso 1 calc R . . C6 C -0.0351(7) 0.7284(4) -0.0311(2) 0.0656(11) Uani 1 d . . . H6 H 0.0568 0.7480 -0.0814 0.079 Uiso 1 calc R . . C7 C -0.2503(6) 0.6268(4) -0.0410(2) 0.0727(12) Uani 1 d . . . H7A H -0.3370 0.6257 0.0143 0.109 Uiso 1 calc R . . H7B H -0.1897 0.5313 -0.0531 0.109 Uiso 1 calc R . . H7C H -0.3635 0.6575 -0.0905 0.109 Uiso 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 0.049(2) 0.0577(16) 0.069(2) -0.0053(17) 0.0097(16) -0.0062(18) N2 0.057(2) 0.0640(18) 0.069(2) -0.0052(17) 0.0190(17) -0.0062(17) N3 0.055(2) 0.0527(18) 0.073(2) 0.0011(16) 0.0062(16) -0.0096(17) C1 0.061(3) 0.0440(18) 0.056(2) 0.004(2) -0.002(2) 0.003(2) C2 0.071(3) 0.068(2) 0.064(2) -0.001(2) 0.014(2) -0.011(2) C3 0.088(3) 0.081(3) 0.060(2) -0.002(2) 0.018(2) 0.003(3) C4 0.090(4) 0.070(3) 0.064(3) -0.001(2) -0.003(3) -0.002(3) C5 0.066(3) 0.069(2) 0.069(3) -0.002(2) 0.004(2) -0.008(2) C6 0.074(3) 0.054(2) 0.069(2) 0.005(2) 0.007(2) -0.005(2) C7 0.074(3) 0.062(2) 0.082(3) 0.000(2) 0.000(2) -0.004(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 N1 C5 1.333(4) . ? N1 C1 1.346(4) . ? N2 C1 1.374(4) . ? N2 N3 1.374(3) . ? N2 HN2 0.8600 . ? N3 C6 1.253(4) . ? C1 C2 1.390(5) . ? C2 C3 1.359(4) . ? C2 H2 0.9300 . ? C3 C4 1.384(5) . ? C3 H3 0.9300 . ? C4 C5 1.369(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.482(5) . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 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 C5 N1 C1 116.2(3) . . ? C1 N2 N3 118.7(3) . . ? C1 N2 HN2 120.7 . . ? N3 N2 HN2 120.7 . . ? C6 N3 N2 118.6(3) . . ? N1 C1 N2 114.6(3) . . ? N1 C1 C2 122.9(3) . . ? N2 C1 C2 122.4(4) . . ? C3 C2 C1 118.0(4) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 121.0(4) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 116.2(4) . . ? C5 C4 H4 121.9 . . ? C3 C4 H4 121.9 . . ? N1 C5 C4 125.6(4) . . ? N1 C5 H5 117.2 . . ? C4 C5 H5 117.2 . . ? N3 C6 C7 121.7(4) . . ? N3 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 HN2 N1 0.86 2.28 3.119(4) 164.8 3_675 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.208 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.057 # Attachment 'CCDC_725114.CIF' # Data for compound 10 (CCDC 725113) data_CCDC_725114 _database_code_depnum_ccdc_archive 'CCDC 725114' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N4' _chemical_formula_sum 'C12 H14 N4' _chemical_formula_weight 214.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 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 13.5774(4) _cell_length_b 7.9769(2) _cell_length_c 22.4305(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.670(3) _cell_angle_gamma 90.00 _cell_volume 2327.25(11) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4076 _cell_measurement_theta_min 2.0569 _cell_measurement_theta_max 66.1369 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89641 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6159 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 66.32 _reflns_number_total 3133 _reflns_number_gt 2750 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _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^)+(0.1000P)^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 constro _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3133 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 N1 N -0.02337(9) -1.19659(16) 0.62596(6) 0.0259(3) Uani 1 1 d . . . N2 N -0.20248(9) -1.34187(15) 0.78466(5) 0.0238(3) Uani 1 1 d . . . N3 N -0.18657(9) -1.25091(15) 0.88253(6) 0.0262(3) Uani 1 1 d . . . N4 N -0.26952(9) -1.35281(15) 0.86234(6) 0.0259(3) Uani 1 1 d . . . C1 C -0.10505(11) -1.2980(2) 0.59575(7) 0.0288(4) Uani 1 1 d . . . H1A H -0.1536 -1.3466 0.6139 0.035 Uiso 1 1 calc R . . C2 C -0.10394(12) -1.3162(2) 0.53596(7) 0.0352(4) Uani 1 1 d . . . H2B H -0.1511 -1.3800 0.5047 0.042 Uiso 1 1 calc R . . C3 C -0.01963(14) -1.2225(3) 0.52847(8) 0.0416(5) Uani 1 1 d . . . H3B H -0.0004 -1.2113 0.4912 0.050 Uiso 1 1 calc R . . C4 C 0.02851(12) -1.1517(2) 0.58400(8) 0.0357(4) Uani 1 1 d . . . H4A H 0.0880 -1.0827 0.5926 0.043 Uiso 1 1 calc R . . C5 C 0.00450(10) -1.14589(18) 0.68819(7) 0.0246(4) Uani 1 1 d . . . H5A H 0.0644 -1.0786 0.7024 0.029 Uiso 1 1 calc R . . C6 C -0.04604(10) -1.18409(18) 0.72926(7) 0.0241(4) Uani 1 1 d . . . H6A H -0.1063 -1.2510 0.7165 0.029 Uiso 1 1 calc R . . C7 C -0.01100(10) -1.12572(18) 0.79296(7) 0.0252(4) Uani 1 1 d . . . H7A H 0.0504 -1.0611 0.8037 0.030 Uiso 1 1 calc R . . C8 C -0.05507(10) -1.15224(18) 0.83850(6) 0.0249(4) Uani 1 1 d . . . H8A H -0.0219 -1.1034 0.8778 0.030 Uiso 1 1 calc R . . C9 C -0.14812(10) -1.24770(17) 0.83435(6) 0.0224(3) Uani 1 1 d . . . C10 C -0.27743(10) -1.40356(18) 0.80441(6) 0.0245(3) Uani 1 1 d . . . H10A H -0.3302 -1.4748 0.7806 0.029 Uiso 1 1 calc R . . C11 C -0.33660(12) -1.3848(2) 0.90164(7) 0.0334(4) Uani 1 1 d . . . H11A H -0.2944 -1.4210 0.9434 0.040 Uiso 1 1 calc R . . H11B H -0.3846 -1.4769 0.8834 0.040 Uiso 1 1 calc R . . C12 C -0.39717(12) -1.2316(2) 0.90810(8) 0.0350(4) Uani 1 1 d . . . H12A H -0.4411 -1.2575 0.9347 0.052 Uiso 1 1 calc R . . H12B H -0.4400 -1.1967 0.8669 0.052 Uiso 1 1 calc R . . H12C H -0.3498 -1.1407 0.9269 0.052 Uiso 1 1 calc R . . N5 N -0.24897(9) -0.76956(16) 0.61998(6) 0.0268(3) Uani 1 1 d . . . N6 N -0.46611(9) -0.69198(16) 0.76647(5) 0.0254(3) Uani 1 1 d . . . N7 N -0.45991(9) -0.80706(15) 0.85965(6) 0.0270(3) Uani 1 1 d . . . N8 N -0.55081(9) -0.72635(15) 0.83522(6) 0.0261(3) Uani 1 1 d . . . C13 C -0.33135(11) -0.67341(19) 0.58673(7) 0.0306(4) Uani 1 1 d . . . H13A H -0.3817 -0.6232 0.6030 0.037 Uiso 1 1 calc R . . C14 C -0.32790(13) -0.6632(2) 0.52699(7) 0.0370(4) Uani 1 1 d . . . H14A H -0.3751 -0.6046 0.4941 0.044 Uiso 1 1 calc R . . C15 C -0.24124(13) -0.7558(2) 0.52245(8) 0.0372(4) Uani 1 1 d . . . H15A H -0.2199 -0.7707 0.4860 0.045 Uiso 1 1 calc R . . C16 C -0.19439(12) -0.8192(2) 0.57972(7) 0.0318(4) Uani 1 1 d . . . H16A H -0.1341 -0.8865 0.5903 0.038 Uiso 1 1 calc R . . C17 C -0.22558(11) -0.81637(18) 0.68255(7) 0.0255(4) Uani 1 1 d . . . H17A H -0.1614 -0.8704 0.7001 0.031 Uiso 1 1 calc R . . C18 C -0.28508(10) -0.79209(18) 0.71980(7) 0.0243(4) Uani 1 1 d . . . H18A H -0.3495 -0.7374 0.7041 0.029 Uiso 1 1 calc R . . C19 C -0.25297(11) -0.84795(18) 0.78390(7) 0.0263(4) Uani 1 1 d . . . H19A H -0.1851 -0.8911 0.7983 0.032 Uiso 1 1 calc R . . C20 C -0.30696(11) -0.84652(18) 0.82554(6) 0.0254(4) Uani 1 1 d . . . H20A H -0.2735 -0.8919 0.8654 0.030 Uiso 1 1 calc R . . C21 C -0.41111(11) -0.78346(18) 0.81683(6) 0.0225(3) Uani 1 1 d . . . C22 C -0.55204(10) -0.65971(18) 0.78046(6) 0.0257(4) Uani 1 1 d . . . H22A H -0.6077 -0.5970 0.7548 0.031 Uiso 1 1 calc R . . C23 C -0.62936(12) -0.7178(2) 0.86785(8) 0.0343(4) Uani 1 1 d . . . H23A H -0.6469 -0.8328 0.8780 0.041 Uiso 1 1 calc R . . H23B H -0.6923 -0.6660 0.8403 0.041 Uiso 1 1 calc R . . C24 C -0.59320(14) -0.6163(3) 0.92749(8) 0.0474(5) Uani 1 1 d . . . H24A H -0.6478 -0.6129 0.9481 0.071 Uiso 1 1 calc R . . H24B H -0.5768 -0.5019 0.9176 0.071 Uiso 1 1 calc R . . H24C H -0.5317 -0.6687 0.9552 0.071 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 0.0211(6) 0.0287(7) 0.0278(6) 0.0040(5) 0.0070(5) -0.0005(5) N2 0.0235(6) 0.0240(6) 0.0248(6) -0.0006(5) 0.0082(5) 0.0008(5) N3 0.0287(6) 0.0251(7) 0.0257(6) 0.0008(5) 0.0090(5) 0.0005(5) N4 0.0309(6) 0.0220(6) 0.0278(6) 0.0016(5) 0.0132(6) 0.0010(5) C1 0.0237(7) 0.0304(8) 0.0296(7) 0.0067(6) 0.0033(6) -0.0015(6) C2 0.0327(8) 0.0400(9) 0.0283(8) 0.0035(7) 0.0013(7) -0.0053(7) C3 0.0421(9) 0.0570(11) 0.0286(8) 0.0018(8) 0.0146(8) -0.0122(9) C4 0.0305(8) 0.0470(10) 0.0332(8) 0.0034(8) 0.0151(7) -0.0115(7) C5 0.0198(6) 0.0241(7) 0.0294(7) 0.0014(6) 0.0065(6) 0.0001(6) C6 0.0191(6) 0.0220(7) 0.0309(8) 0.0014(6) 0.0068(6) 0.0014(6) C7 0.0187(6) 0.0231(7) 0.0324(8) -0.0018(6) 0.0047(6) 0.0018(6) C8 0.0216(6) 0.0256(7) 0.0252(7) -0.0028(6) 0.0030(6) 0.0031(6) C9 0.0223(6) 0.0215(7) 0.0230(6) 0.0025(6) 0.0062(6) 0.0051(6) C10 0.0249(6) 0.0226(7) 0.0265(7) 0.0013(6) 0.0080(6) -0.0005(6) C11 0.0429(8) 0.0291(8) 0.0349(8) 0.0016(7) 0.0221(7) -0.0036(7) C12 0.0330(8) 0.0408(9) 0.0361(8) 0.0051(7) 0.0180(7) 0.0050(7) N5 0.0233(6) 0.0271(7) 0.0310(7) -0.0028(5) 0.0095(6) -0.0043(5) N6 0.0233(6) 0.0267(7) 0.0251(6) 0.0012(5) 0.0050(5) 0.0013(5) N7 0.0303(6) 0.0237(6) 0.0279(6) 0.0016(5) 0.0099(6) 0.0042(5) N8 0.0264(6) 0.0236(6) 0.0289(6) -0.0010(5) 0.0090(6) 0.0002(5) C13 0.0277(7) 0.0270(8) 0.0359(8) 0.0019(6) 0.0071(7) -0.0040(6) C14 0.0385(8) 0.0353(9) 0.0332(8) 0.0055(7) 0.0038(7) -0.0100(7) C15 0.0416(9) 0.0403(10) 0.0326(8) -0.0049(7) 0.0153(8) -0.0126(8) C16 0.0293(7) 0.0366(9) 0.0344(8) -0.0078(7) 0.0169(7) -0.0067(7) C17 0.0208(6) 0.0244(7) 0.0298(8) -0.0020(6) 0.0047(7) -0.0018(6) C18 0.0190(6) 0.0229(7) 0.0309(7) -0.0016(6) 0.0068(6) 0.0005(6) C19 0.0214(6) 0.0221(7) 0.0328(8) -0.0010(6) 0.0034(6) 0.0018(6) C20 0.0268(7) 0.0230(7) 0.0244(7) 0.0011(6) 0.0041(6) 0.0034(6) C21 0.0257(7) 0.0200(7) 0.0219(6) -0.0009(6) 0.0071(6) -0.0020(6) C22 0.0231(7) 0.0261(7) 0.0263(7) 0.0012(6) 0.0046(6) 0.0005(6) C23 0.0357(8) 0.0285(8) 0.0466(9) 0.0055(7) 0.0247(8) 0.0039(7) C24 0.0468(9) 0.0653(13) 0.0328(8) 0.0035(9) 0.0160(8) 0.0238(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 N1 C4 1.375(2) . ? N1 C1 1.3830(19) . ? N1 C5 1.3972(19) . ? N2 C10 1.3163(19) . ? N2 C9 1.3708(18) . ? N3 C9 1.3286(19) . ? N3 N4 1.3571(18) . ? N4 C10 1.3355(18) . ? N4 C11 1.4603(19) . ? C1 C2 1.353(2) . ? C1 H1A 0.9500 . ? C2 C3 1.417(3) . ? C2 H2B 0.9500 . ? C3 C4 1.353(2) . ? C3 H3B 0.9500 . ? C4 H4A 0.9500 . ? C5 C6 1.332(2) . ? C5 H5A 0.9500 . ? C6 C7 1.4472(19) . ? C6 H6A 0.9500 . ? C7 C8 1.341(2) . ? C7 H7A 0.9500 . ? C8 C9 1.455(2) . ? C8 H8A 0.9500 . ? C10 H10A 0.9500 . ? C11 C12 1.503(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N5 C16 1.380(2) . ? N5 C13 1.3845(19) . ? N5 C17 1.3978(19) . ? N6 C22 1.3176(19) . ? N6 C21 1.3719(18) . ? N7 C21 1.328(2) . ? N7 N8 1.3602(17) . ? N8 C22 1.3342(19) . ? N8 C23 1.458(2) . ? C13 C14 1.357(2) . ? C13 H13A 0.9500 . ? C14 C15 1.417(3) . ? C14 H14A 0.9500 . ? C15 C16 1.357(2) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 C18 1.333(2) . ? C17 H17A 0.9500 . ? C18 C19 1.448(2) . ? C18 H18A 0.9500 . ? C19 C20 1.343(2) . ? C19 H19A 0.9500 . ? C20 C21 1.460(2) . ? C20 H20A 0.9500 . ? C22 H22A 0.9500 . ? C23 C24 1.520(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 C1 108.27(12) . . ? C4 N1 C5 124.28(12) . . ? C1 N1 C5 127.45(13) . . ? C10 N2 C9 102.66(12) . . ? C9 N3 N4 102.84(11) . . ? C10 N4 N3 109.50(12) . . ? C10 N4 C11 130.12(13) . . ? N3 N4 C11 120.32(12) . . ? C2 C1 N1 108.22(14) . . ? C2 C1 H1A 125.9 . . ? N1 C1 H1A 125.9 . . ? C1 C2 C3 107.48(14) . . ? C1 C2 H2B 126.3 . . ? C3 C2 H2B 126.3 . . ? C4 C3 C2 107.71(16) . . ? C4 C3 H3B 126.1 . . ? C2 C3 H3B 126.1 . . ? C3 C4 N1 108.32(15) . . ? C3 C4 H4A 125.8 . . ? N1 C4 H4A 125.8 . . ? C6 C5 N1 125.38(13) . . ? C6 C5 H5A 117.3 . . ? N1 C5 H5A 117.3 . . ? C5 C6 C7 121.35(13) . . ? C5 C6 H6A 119.3 . . ? C7 C6 H6A 119.3 . . ? C8 C7 C6 127.54(13) . . ? C8 C7 H7A 116.2 . . ? C6 C7 H7A 116.2 . . ? C7 C8 C9 127.08(13) . . ? C7 C8 H8A 116.5 . . ? C9 C8 H8A 116.5 . . ? N3 C9 N2 113.91(13) . . ? N3 C9 C8 119.64(12) . . ? N2 C9 C8 126.44(14) . . ? N2 C10 N4 111.10(12) . . ? N2 C10 H10A 124.5 . . ? N4 C10 H10A 124.5 . . ? N4 C11 C12 111.69(13) . . ? N4 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N4 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C16 N5 C13 107.99(13) . . ? C16 N5 C17 124.75(13) . . ? C13 N5 C17 127.20(13) . . ? C22 N6 C21 102.59(12) . . ? C21 N7 N8 103.00(11) . . ? C22 N8 N7 109.25(12) . . ? C22 N8 C23 128.75(12) . . ? N7 N8 C23 121.98(12) . . ? C14 C13 N5 108.28(15) . . ? C14 C13 H13A 125.9 . . ? N5 C13 H13A 125.9 . . ? C13 C14 C15 107.72(15) . . ? C13 C14 H14A 126.1 . . ? C15 C14 H14A 126.1 . . ? C16 C15 C14 107.44(16) . . ? C16 C15 H15A 126.3 . . ? C14 C15 H15A 126.3 . . ? C15 C16 N5 108.56(15) . . ? C15 C16 H16A 125.7 . . ? N5 C16 H16A 125.7 . . ? C18 C17 N5 125.92(13) . . ? C18 C17 H17A 117.0 . . ? N5 C17 H17A 117.0 . . ? C17 C18 C19 120.93(13) . . ? C17 C18 H18A 119.5 . . ? C19 C18 H18A 119.5 . . ? C20 C19 C18 128.26(13) . . ? C20 C19 H19A 115.9 . . ? C18 C19 H19A 115.9 . . ? C19 C20 C21 127.65(12) . . ? C19 C20 H20A 116.2 . . ? C21 C20 H20A 116.2 . . ? N7 C21 N6 113.86(13) . . ? N7 C21 C20 121.30(12) . . ? N6 C21 C20 124.82(14) . . ? N6 C22 N8 111.30(12) . . ? N6 C22 H22A 124.3 . . ? N8 C22 H22A 124.3 . . ? N8 C23 C24 111.63(14) . . ? N8 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? N8 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.766 _diffrn_reflns_theta_full 66.32 _diffrn_measured_fraction_theta_full 0.765 _refine_diff_density_max 0.147 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.029