# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Schubert, Ulrich' _publ_contact_author_email ulrich.schubert@uni-jena.de _publ_section_title ; Unexpected metal-mediated oxidation of hydroxymethyl groups to coordinated carboxylate groups by bis-cyclometalated iridium(III) centers ; loop_ _publ_author_name B.Beyer C.Ulbricht A.Winter M.Hager R.Hoogenboom N.Herzer ; S.Baumann ; G.Kickelbrick H.Gorls U.Schubert # Attachment '- structures_2d_2e_2g_final.cif' data_sb055 _database_code_depnum_ccdc_archive 'CCDC 726545' #TrackingRef '- structures_2d_2e_2g_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N3' _chemical_formula_sum 'C16 H15 N3' _chemical_formula_weight 249.31 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 0.0000 '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 0.0000 '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 n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 10.983(2) _cell_length_b 10.056(2) _cell_length_c 12.375(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1366.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5376 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.605 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9612 _exptl_absorpt_correction_T_max 0.9897 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker-AXS KAPPA APEX II CCD Detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19525 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 29.31 _reflns_number_total 1953 _reflns_number_gt 1532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-AXS APEX 2 Software' _computing_cell_refinement 'Bruker-AXS APEX 2 Software' _computing_data_reduction 'Bruker-AXS APEX 2 Software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker-AXS SHELXTL Software' _computing_publication_material 'Bruker-AXS SHELXTL Software' _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^)+(0.0534P)^2^+0.0796P] 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 0(10) _chemical_absolute_configuration unk _refine_ls_number_reflns 1953 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.085 _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 0.55904(13) 0.21284(17) 0.47020(13) 0.0482(4) Uani 1 1 d . . . N2 N 0.67456(16) 0.2510(2) 0.49036(16) 0.0658(5) Uani 1 1 d . . . N3 N 0.67912(16) 0.2930(2) 0.58995(17) 0.0648(5) Uani 1 1 d . . . C4 C 0.56658(16) 0.28253(19) 0.63508(16) 0.0486(4) Uani 1 1 d . . . C5 C 0.49024(16) 0.23223(19) 0.55920(16) 0.0473(4) Uani 1 1 d . . . H5 H 0.4075 0.2147 0.5669 0.057 Uiso 1 1 calc R . . C6 C 0.52619(18) 0.16412(19) 0.36596(16) 0.0474(4) Uani 1 1 d . . . C7 C 0.40986(18) 0.1165(2) 0.34680(17) 0.0534(5) Uani 1 1 d . . . H7 H 0.3531 0.1141 0.4026 0.064 Uiso 1 1 calc R . . C8 C 0.37790(19) 0.0723(2) 0.2442(2) 0.0583(5) Uani 1 1 d . . . C9 C 0.4632(2) 0.0784(2) 0.16256(19) 0.0615(5) Uani 1 1 d . . . H9 H 0.4412 0.0512 0.0934 0.074 Uiso 1 1 calc R . . C10 C 0.5807(2) 0.1240(2) 0.18050(18) 0.0583(5) Uani 1 1 d . . . C11 C 0.6125(2) 0.1667(2) 0.28365(18) 0.0544(5) Uani 1 1 d . . . H11 H 0.6910 0.1969 0.2975 0.065 Uiso 1 1 calc R . . C12 C 0.2523(2) 0.0164(3) 0.2241(3) 0.0830(8) Uani 1 1 d . . . H12A H 0.2299 0.0312 0.1500 0.125 Uiso 1 1 calc R . . H12B H 0.1947 0.0597 0.2706 0.125 Uiso 1 1 calc R . . H12C H 0.2524 -0.0774 0.2387 0.125 Uiso 1 1 calc R . . C13 C 0.6745(3) 0.1278(3) 0.0914(2) 0.0795(7) Uani 1 1 d . . . H13A H 0.7321 0.1974 0.1057 0.119 Uiso 1 1 calc R . . H13B H 0.6349 0.1445 0.0236 0.119 Uiso 1 1 calc R . . H13C H 0.7162 0.0440 0.0882 0.119 Uiso 1 1 calc R . . C14 C 0.54370(18) 0.3210(2) 0.74821(17) 0.0529(5) Uani 1 1 d . . . C15 C 0.6122(2) 0.4188(3) 0.7981(2) 0.0733(6) Uani 1 1 d . . . H15 H 0.6754 0.4594 0.7605 0.088 Uiso 1 1 calc R . . C16 C 0.5877(3) 0.4569(4) 0.9033(3) 0.0901(9) Uani 1 1 d . . . H16 H 0.6340 0.5232 0.9358 0.108 Uiso 1 1 calc R . . C17 C 0.4956(3) 0.3970(4) 0.9595(2) 0.0907(9) Uani 1 1 d . . . H17 H 0.4782 0.4237 1.0298 0.109 Uiso 1 1 calc R . . C18 C 0.4293(3) 0.2983(3) 0.9125(2) 0.0846(8) Uani 1 1 d . . . H18 H 0.3682 0.2562 0.9517 0.101 Uiso 1 1 calc R . . C19 C 0.4518(2) 0.2595(3) 0.80638(19) 0.0653(6) Uani 1 1 d . . . H19 H 0.4054 0.1927 0.7747 0.078 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 0.0375(7) 0.0573(9) 0.0498(9) 0.0047(7) 0.0095(7) 0.0009(6) N2 0.0395(9) 0.0987(14) 0.0591(11) -0.0017(10) 0.0114(8) -0.0068(8) N3 0.0419(9) 0.0936(13) 0.0590(11) -0.0046(10) 0.0088(8) -0.0086(8) C4 0.0416(9) 0.0526(10) 0.0516(11) 0.0047(8) 0.0053(8) 0.0052(7) C5 0.0372(8) 0.0540(10) 0.0507(9) 0.0027(8) 0.0108(8) 0.0039(7) C6 0.0469(9) 0.0470(9) 0.0483(10) 0.0034(8) 0.0107(8) 0.0048(7) C7 0.0483(10) 0.0549(11) 0.0568(12) 0.0005(9) 0.0120(9) 0.0009(8) C8 0.0619(11) 0.0470(10) 0.0661(13) -0.0061(9) 0.0025(10) 0.0009(8) C9 0.0801(15) 0.0516(11) 0.0528(12) -0.0066(9) 0.0030(11) 0.0073(10) C10 0.0694(13) 0.0519(11) 0.0537(12) 0.0020(9) 0.0176(10) 0.0075(10) C11 0.0513(11) 0.0571(11) 0.0548(11) 0.0024(9) 0.0157(9) 0.0035(8) C12 0.0754(15) 0.0804(16) 0.0933(19) -0.0235(15) -0.0006(15) -0.0141(13) C13 0.0929(18) 0.0900(16) 0.0556(14) -0.0027(13) 0.0289(13) 0.0090(14) C14 0.0471(9) 0.0599(11) 0.0517(11) 0.0030(9) 0.0030(8) 0.0124(8) C15 0.0721(14) 0.0801(15) 0.0676(15) -0.0094(13) 0.0039(12) -0.0044(12) C16 0.104(2) 0.096(2) 0.0708(17) -0.0216(16) -0.0088(16) 0.0078(17) C17 0.104(2) 0.113(2) 0.0554(15) -0.0150(15) 0.0072(15) 0.0306(19) C18 0.090(2) 0.104(2) 0.0598(15) 0.0043(14) 0.0240(14) 0.0155(17) C19 0.0614(13) 0.0780(14) 0.0566(12) 0.0003(11) 0.0127(10) 0.0059(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 N2 1.349(2) . ? N1 C5 1.350(2) . ? N1 C6 1.426(3) . ? N2 N3 1.304(3) . ? N3 C4 1.360(2) . ? C4 C5 1.357(3) . ? C4 C14 1.474(3) . ? C5 H5 0.9300 . ? C6 C7 1.385(3) . ? C6 C11 1.391(3) . ? C7 C8 1.390(3) . ? C7 H7 0.9300 . ? C8 C9 1.379(3) . ? C8 C12 1.510(3) . ? C9 C10 1.388(3) . ? C9 H9 0.9300 . ? C10 C11 1.391(3) . ? C10 C13 1.510(3) . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.383(3) . ? C14 C19 1.386(3) . ? C15 C16 1.383(4) . ? C15 H15 0.9300 . ? C16 C17 1.368(5) . ? C16 H16 0.9300 . ? C17 C18 1.362(5) . ? C17 H17 0.9300 . ? C18 C19 1.391(4) . ? C18 H18 0.9300 . ? C19 H19 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 N2 N1 C5 109.55(17) . . ? N2 N1 C6 120.19(15) . . ? C5 N1 C6 130.24(16) . . ? N3 N2 N1 107.64(17) . . ? N2 N3 C4 109.17(19) . . ? C5 C4 N3 107.82(18) . . ? C5 C4 C14 130.53(17) . . ? N3 C4 C14 121.64(18) . . ? N1 C5 C4 105.82(15) . . ? N1 C5 H5 127.1 . . ? C4 C5 H5 127.1 . . ? C7 C6 C11 120.6(2) . . ? C7 C6 N1 120.46(16) . . ? C11 C6 N1 118.91(17) . . ? C6 C7 C8 119.99(18) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 118.90(19) . . ? C9 C8 C12 121.1(2) . . ? C7 C8 C12 120.0(2) . . ? C8 C9 C10 122.0(2) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C11 118.83(19) . . ? C9 C10 C13 121.8(2) . . ? C11 C10 C13 119.4(2) . . ? C6 C11 C10 119.7(2) . . ? C6 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 118.8(2) . . ? C15 C14 C4 121.2(2) . . ? C19 C14 C4 120.0(2) . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C16 119.9(3) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.8(3) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C14 C19 C18 119.6(3) . . ? C14 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? 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 C5 N1 N2 N3 0.3(3) . . . . ? C6 N1 N2 N3 178.94(19) . . . . ? N1 N2 N3 C4 -0.1(3) . . . . ? N2 N3 C4 C5 -0.1(3) . . . . ? N2 N3 C4 C14 179.2(2) . . . . ? N2 N1 C5 C4 -0.4(2) . . . . ? C6 N1 C5 C4 -178.83(17) . . . . ? N3 C4 C5 N1 0.3(2) . . . . ? C14 C4 C5 N1 -178.91(18) . . . . ? N2 N1 C6 C7 175.69(19) . . . . ? C5 N1 C6 C7 -6.0(3) . . . . ? N2 N1 C6 C11 -5.1(3) . . . . ? C5 N1 C6 C11 173.21(18) . . . . ? C11 C6 C7 C8 -0.8(3) . . . . ? N1 C6 C7 C8 178.44(19) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C6 C7 C8 C12 178.1(2) . . . . ? C7 C8 C9 C10 1.8(3) . . . . ? C12 C8 C9 C10 -177.1(2) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C8 C9 C10 C13 178.7(2) . . . . ? C7 C6 C11 C10 1.5(3) . . . . ? N1 C6 C11 C10 -177.71(18) . . . . ? C9 C10 C11 C6 -0.6(3) . . . . ? C13 C10 C11 C6 179.7(2) . . . . ? C5 C4 C14 C15 -151.9(2) . . . . ? N3 C4 C14 C15 29.0(3) . . . . ? C5 C4 C14 C19 27.8(3) . . . . ? N3 C4 C14 C19 -151.4(2) . . . . ? C19 C14 C15 C16 -1.5(4) . . . . ? C4 C14 C15 C16 178.2(2) . . . . ? C14 C15 C16 C17 0.5(5) . . . . ? C15 C16 C17 C18 1.1(5) . . . . ? C16 C17 C18 C19 -1.8(5) . . . . ? C15 C14 C19 C18 0.9(3) . . . . ? C4 C14 C19 C18 -178.8(2) . . . . ? C17 C18 C19 C14 0.7(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.31 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.141 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.025 #===== END #================================================= data_use32 _database_code_depnum_ccdc_archive 'CCDC 726546' #TrackingRef '- structures_2d_2e_2g_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N3 O' _chemical_formula_sum 'C15 H13 N3 O' _chemical_formula_weight 251.28 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.0879(4) _cell_length_b 9.1648(4) _cell_length_c 29.4080(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2449.36(19) _cell_formula_units_Z 8 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2752 _cell_measurement_theta_min 5.254 _cell_measurement_theta_max 56.428 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9356 _exptl_absorpt_correction_T_max 0.9790 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 'Bruker-AXS SMART CCD Detector' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19846 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0137 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 28.33 _reflns_number_total 3038 _reflns_number_gt 2452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-AXS SMART Software' _computing_cell_refinement 'Bruker-AXS SAINT Software' _computing_data_reduction 'Bruker-AXS SAINT Software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker-AXS SHELXTL Software' _computing_publication_material 'Bruker-AXS SHELXTL Software' _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^)+(0.0798P)^2^+0.3381P] 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 3038 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1377 _refine_ls_wR_factor_gt 0.1254 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 O13 O 0.25448(12) 0.26548(12) 0.00696(3) 0.0602(3) Uani 1 1 d . . . H13 H 0.277(2) 0.194(2) 0.0249(7) 0.087(6) Uiso 1 1 d . . . N1 N 0.11800(11) 0.45399(11) 0.13536(3) 0.0432(2) Uani 1 1 d . . . N2 N 0.15764(14) 0.57219(12) 0.11094(4) 0.0547(3) Uani 1 1 d . . . N3 N 0.15505(14) 0.53300(12) 0.06810(4) 0.0547(3) Uani 1 1 d . . . C4 C 0.11465(13) 0.39119(14) 0.06468(4) 0.0455(3) Uani 1 1 d . . . C5 C 0.08979(14) 0.33994(14) 0.10753(4) 0.0458(3) Uani 1 1 d . . . H5A H 0.0599 0.2466 0.1158 0.055 Uiso 1 1 calc R . . C6 C 0.11719(12) 0.46144(12) 0.18372(4) 0.0411(3) Uani 1 1 d . . . C7 C 0.03092(15) 0.36795(15) 0.20907(4) 0.0508(3) Uani 1 1 d . . . H7A H -0.0294 0.3003 0.1946 0.061 Uiso 1 1 calc R . . C8 C 0.03451(15) 0.37535(15) 0.25605(4) 0.0508(3) Uani 1 1 d . . . H8A H -0.0232 0.3109 0.2727 0.061 Uiso 1 1 calc R . . C9 C 0.12154(12) 0.47606(12) 0.27925(4) 0.0403(3) Uani 1 1 d . . . C10 C 0.20636(15) 0.56910(14) 0.25249(4) 0.0513(3) Uani 1 1 d . . . H10A H 0.2657 0.6380 0.2667 0.062 Uiso 1 1 calc R . . C11 C 0.20543(16) 0.56250(14) 0.20565(4) 0.0512(3) Uani 1 1 d . . . H11A H 0.2640 0.6258 0.1888 0.061 Uiso 1 1 calc R . . C12 C 0.11275(15) 0.31231(17) 0.02022(4) 0.0549(3) Uani 1 1 d . . . H12A H 0.0484 0.2282 0.0226 0.066 Uiso 1 1 calc R . . H12B H 0.0731 0.3763 -0.0030 0.066 Uiso 1 1 calc R . . C14 C 0.12424(12) 0.48414(13) 0.32988(4) 0.0422(3) Uani 1 1 d . . . C15 C 0.02310(15) 0.40796(15) 0.35645(4) 0.0523(3) Uani 1 1 d . . . H15A H -0.0481 0.3509 0.3423 0.063 Uiso 1 1 calc R . . C16 C 0.02636(17) 0.41539(17) 0.40354(5) 0.0588(4) Uani 1 1 d . . . H16A H -0.0421 0.3632 0.4205 0.071 Uiso 1 1 calc R . . C17 C 0.13028(17) 0.49962(18) 0.42539(5) 0.0600(4) Uani 1 1 d . . . H17A H 0.1325 0.5046 0.4570 0.072 Uiso 1 1 calc R . . C18 C 0.2310(2) 0.57640(19) 0.39968(5) 0.0676(4) Uani 1 1 d . . . H18A H 0.3014 0.6338 0.4141 0.081 Uiso 1 1 calc R . . C19 C 0.22857(16) 0.56895(17) 0.35266(5) 0.0576(3) Uani 1 1 d . . . H19A H 0.2976 0.6213 0.3360 0.069 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 O13 0.0738(7) 0.0637(6) 0.0431(5) 0.0078(4) 0.0112(4) 0.0106(5) N1 0.0491(5) 0.0401(5) 0.0405(5) 0.0016(4) 0.0017(4) 0.0028(4) N2 0.0741(7) 0.0438(6) 0.0462(6) 0.0058(4) 0.0025(5) -0.0032(5) N3 0.0680(7) 0.0513(6) 0.0447(6) 0.0069(4) 0.0010(5) -0.0013(5) C4 0.0454(6) 0.0501(7) 0.0412(6) 0.0041(5) -0.0015(4) 0.0038(5) C5 0.0528(7) 0.0427(6) 0.0419(6) 0.0004(5) 0.0005(5) -0.0007(5) C6 0.0445(6) 0.0392(6) 0.0394(5) -0.0011(4) 0.0022(4) 0.0060(4) C7 0.0548(7) 0.0532(7) 0.0445(6) -0.0046(5) 0.0002(5) -0.0125(6) C8 0.0556(7) 0.0524(7) 0.0442(6) 0.0001(5) 0.0051(5) -0.0123(6) C9 0.0401(6) 0.0386(6) 0.0421(6) -0.0016(4) 0.0009(4) 0.0061(4) C10 0.0573(7) 0.0485(6) 0.0482(7) -0.0053(5) 0.0008(5) -0.0107(6) C11 0.0589(7) 0.0474(6) 0.0473(7) 0.0001(5) 0.0057(5) -0.0106(6) C12 0.0609(8) 0.0641(8) 0.0396(6) 0.0015(5) -0.0050(5) 0.0012(6) C14 0.0444(6) 0.0410(6) 0.0413(6) -0.0012(4) -0.0016(4) 0.0071(4) C15 0.0546(7) 0.0562(8) 0.0462(7) -0.0005(5) 0.0006(5) -0.0050(6) C16 0.0677(9) 0.0619(8) 0.0468(7) 0.0053(6) 0.0064(6) 0.0004(7) C17 0.0772(10) 0.0617(8) 0.0410(6) -0.0004(6) -0.0046(6) 0.0093(7) C18 0.0789(10) 0.0736(10) 0.0503(8) -0.0059(7) -0.0137(7) -0.0120(8) C19 0.0602(8) 0.0643(8) 0.0485(7) -0.0008(6) -0.0033(6) -0.0112(6) _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 O13 C12 1.4126(17) . ? O13 H13 0.87(2) . ? N1 N2 1.3487(14) . ? N1 C5 1.3521(16) . ? N1 C6 1.4239(15) . ? N2 N3 1.3101(15) . ? N3 C4 1.3543(18) . ? C4 C5 1.3635(16) . ? C4 C12 1.4942(18) . ? C5 H5A 0.9300 . ? C6 C7 1.3800(17) . ? C6 C11 1.3844(17) . ? C7 C8 1.3838(17) . ? C7 H7A 0.9300 . ? C8 C9 1.3938(17) . ? C8 H8A 0.9300 . ? C9 C10 1.3930(17) . ? C9 C14 1.4910(16) . ? C10 C11 1.3790(17) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C14 C15 1.3938(18) . ? C14 C19 1.3971(18) . ? C15 C16 1.3869(18) . ? C15 H15A 0.9300 . ? C16 C17 1.379(2) . ? C16 H16A 0.9300 . ? C17 C18 1.380(2) . ? C17 H17A 0.9300 . ? C18 C19 1.3847(19) . ? C18 H18A 0.9300 . ? C19 H19A 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 C12 O13 H13 106.0(13) . . ? N2 N1 C5 110.44(10) . . ? N2 N1 C6 119.65(10) . . ? C5 N1 C6 129.85(10) . . ? N3 N2 N1 106.68(10) . . ? N2 N3 C4 109.84(10) . . ? N3 C4 C5 107.87(11) . . ? N3 C4 C12 122.17(11) . . ? C5 C4 C12 129.80(13) . . ? N1 C5 C4 105.17(11) . . ? N1 C5 H5A 127.4 . . ? C4 C5 H5A 127.4 . . ? C7 C6 C11 119.53(11) . . ? C7 C6 N1 120.84(11) . . ? C11 C6 N1 119.62(11) . . ? C6 C7 C8 119.70(11) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C7 C8 C9 122.31(11) . . ? C7 C8 H8A 118.8 . . ? C9 C8 H8A 118.8 . . ? C10 C9 C8 116.29(11) . . ? C10 C9 C14 121.64(10) . . ? C8 C9 C14 122.07(10) . . ? C11 C10 C9 122.28(11) . . ? C11 C10 H10A 118.9 . . ? C9 C10 H10A 118.9 . . ? C10 C11 C6 119.88(11) . . ? C10 C11 H11A 120.1 . . ? C6 C11 H11A 120.1 . . ? O13 C12 C4 112.21(11) . . ? O13 C12 H12A 109.2 . . ? C4 C12 H12A 109.2 . . ? O13 C12 H12B 109.2 . . ? C4 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C15 C14 C19 117.22(12) . . ? C15 C14 C9 121.60(11) . . ? C19 C14 C9 121.18(11) . . ? C16 C15 C14 121.40(12) . . ? C16 C15 H15A 119.3 . . ? C14 C15 H15A 119.3 . . ? C17 C16 C15 120.50(13) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 119.00(13) . . ? C16 C17 H17A 120.5 . . ? C18 C17 H17A 120.5 . . ? C17 C18 C19 120.73(14) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C18 C19 C14 121.15(13) . . ? C18 C19 H19A 119.4 . . ? C14 C19 H19A 119.4 . . ? 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 C5 N1 N2 N3 -0.24(14) . . . . ? C6 N1 N2 N3 177.16(10) . . . . ? N1 N2 N3 C4 -0.15(14) . . . . ? N2 N3 C4 C5 0.47(15) . . . . ? N2 N3 C4 C12 -175.31(11) . . . . ? N2 N1 C5 C4 0.52(14) . . . . ? C6 N1 C5 C4 -176.54(11) . . . . ? N3 C4 C5 N1 -0.60(14) . . . . ? C12 C4 C5 N1 174.76(12) . . . . ? N2 N1 C6 C7 156.53(12) . . . . ? C5 N1 C6 C7 -26.64(19) . . . . ? N2 N1 C6 C11 -24.29(17) . . . . ? C5 N1 C6 C11 152.55(13) . . . . ? C11 C6 C7 C8 -0.57(19) . . . . ? N1 C6 C7 C8 178.62(11) . . . . ? C6 C7 C8 C9 0.8(2) . . . . ? C7 C8 C9 C10 -0.45(19) . . . . ? C7 C8 C9 C14 179.61(12) . . . . ? C8 C9 C10 C11 -0.20(19) . . . . ? C14 C9 C10 C11 179.74(12) . . . . ? C9 C10 C11 C6 0.5(2) . . . . ? C7 C6 C11 C10 -0.1(2) . . . . ? N1 C6 C11 C10 -179.26(11) . . . . ? N3 C4 C12 O13 79.97(16) . . . . ? C5 C4 C12 O13 -94.80(16) . . . . ? C10 C9 C14 C15 169.64(12) . . . . ? C8 C9 C14 C15 -10.42(17) . . . . ? C10 C9 C14 C19 -10.25(18) . . . . ? C8 C9 C14 C19 169.69(13) . . . . ? C19 C14 C15 C16 -0.3(2) . . . . ? C9 C14 C15 C16 179.77(12) . . . . ? C14 C15 C16 C17 0.3(2) . . . . ? C15 C16 C17 C18 0.0(2) . . . . ? C16 C17 C18 C19 -0.2(3) . . . . ? C17 C18 C19 C14 0.2(3) . . . . ? C15 C14 C19 C18 0.1(2) . . . . ? C9 C14 C19 C18 -179.99(13) . . . . ? 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 O13 H13 N3 0.87(2) 2.04(2) 2.9067(15) 175.4(19) 8_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.207 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.064 #==== END #============================================================================== data_FO3562 _database_code_depnum_ccdc_archive 'CCDC 726547' #TrackingRef '- structures_2d_2e_2g_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H13 N3 O' _chemical_formula_sum 'C11 H13 N3 O' _chemical_formula_weight 203.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc 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 7.4938(4) _cell_length_b 8.0177(3) _cell_length_c 17.8009(11) _cell_angle_alpha 90.00 _cell_angle_beta 93.744(3) _cell_angle_gamma 90.00 _cell_volume 1067.25(10) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 7341 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.085 _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 183(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 KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7341 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2435 _reflns_number_gt 1586 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0735P)^2^+0.3513P] 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 2435 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.004 _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 O15 O 0.1208(2) 0.73439(18) 0.45280(8) 0.0270(4) Uani 1 1 d . . . H15 H 0.123(4) 0.629(4) 0.4417(16) 0.056(8) Uiso 1 1 d . . . N2 N -0.2857(2) 0.6457(2) 0.60696(10) 0.0296(4) Uani 1 1 d . . . N3 N -0.1315(2) 0.6068(2) 0.58025(10) 0.0283(4) Uani 1 1 d . . . N1 N -0.2911(2) 0.8137(2) 0.61085(9) 0.0231(4) Uani 1 1 d . . . C4 C -0.0381(3) 0.7489(2) 0.56660(11) 0.0228(4) Uani 1 1 d . . . C5 C -0.1395(3) 0.8813(2) 0.58624(11) 0.0226(4) Uani 1 1 d . . . H5 H -0.121(3) 0.999(3) 0.5852(12) 0.031(6) Uiso 1 1 d . . . C6 C -0.4448(3) 0.8969(2) 0.63700(11) 0.0223(4) Uani 1 1 d . . . C7 C -0.4790(3) 1.0601(3) 0.61409(12) 0.0252(5) Uani 1 1 d . . . H7 H -0.402(3) 1.114(3) 0.5802(13) 0.035(6) Uiso 1 1 d . . . C8 C -0.6262(3) 1.1432(2) 0.63959(12) 0.0269(5) Uani 1 1 d . . . C9 C -0.7376(3) 1.0582(3) 0.68602(12) 0.0276(5) Uani 1 1 d . . . H9 H -0.846(3) 1.117(3) 0.7030(14) 0.039(6) Uiso 1 1 d . . . C10 C -0.7047(3) 0.8939(3) 0.70843(11) 0.0264(5) Uani 1 1 d . . . C11 C -0.5543(3) 0.8138(3) 0.68416(11) 0.0245(5) Uani 1 1 d . . . H11 H -0.528(3) 0.702(3) 0.6982(13) 0.031(6) Uiso 1 1 d . . . C12 C -0.6629(3) 1.3222(3) 0.61689(15) 0.0363(6) Uani 1 1 d . . . H12A H -0.6067 1.3462 0.5699 0.054 Uiso 1 1 calc R . . H12B H -0.6135 1.3969 0.6566 0.054 Uiso 1 1 calc R . . H12C H -0.7923 1.3398 0.6095 0.054 Uiso 1 1 calc R . . C13 C -0.8289(3) 0.8045(3) 0.75796(14) 0.0375(6) Uani 1 1 d . . . H13A H -0.8398 0.6875 0.7424 0.056 Uiso 1 1 calc R . . H13B H -0.9470 0.8575 0.7533 0.056 Uiso 1 1 calc R . . H13C H -0.7810 0.8104 0.8104 0.056 Uiso 1 1 calc R . . C14 C 0.1387(3) 0.7457(3) 0.53277(12) 0.0253(5) Uani 1 1 d . . . H14A H 0.203(3) 0.855(3) 0.5450(12) 0.027(6) Uiso 1 1 d . . . H14B H 0.204(3) 0.657(3) 0.5539(13) 0.028(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O15 0.0373(9) 0.0180(7) 0.0268(8) -0.0021(6) 0.0097(6) 0.0002(6) N2 0.0343(10) 0.0182(9) 0.0378(11) -0.0012(7) 0.0132(8) -0.0002(8) N3 0.0338(10) 0.0195(8) 0.0328(10) -0.0004(7) 0.0111(8) -0.0003(8) N1 0.0248(9) 0.0170(8) 0.0278(9) -0.0002(7) 0.0044(7) 0.0008(7) C4 0.0281(11) 0.0190(10) 0.0211(10) 0.0008(8) 0.0004(8) 0.0001(8) C5 0.0239(10) 0.0174(9) 0.0270(11) 0.0009(8) 0.0044(8) -0.0011(8) C6 0.0220(10) 0.0220(10) 0.0228(10) -0.0035(8) 0.0015(8) -0.0012(8) C7 0.0251(11) 0.0223(10) 0.0285(11) -0.0004(8) 0.0033(9) -0.0029(8) C8 0.0238(10) 0.0223(10) 0.0343(12) -0.0024(9) -0.0015(9) 0.0003(9) C9 0.0230(11) 0.0299(11) 0.0300(12) -0.0052(9) 0.0028(9) 0.0014(9) C10 0.0250(10) 0.0325(11) 0.0217(10) -0.0023(8) 0.0025(8) -0.0026(9) C11 0.0278(11) 0.0233(10) 0.0223(11) 0.0022(8) 0.0009(8) 0.0004(9) C12 0.0313(12) 0.0254(11) 0.0523(15) 0.0023(10) 0.0030(11) 0.0041(10) C13 0.0359(13) 0.0442(13) 0.0337(13) 0.0053(10) 0.0121(10) -0.0007(11) C14 0.0256(10) 0.0224(10) 0.0282(11) -0.0010(9) 0.0032(9) 0.0024(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 O15 C14 1.424(3) . ? O15 H15 0.87(3) . ? N2 N3 1.315(2) . ? N2 N1 1.350(2) . ? N3 C4 1.367(3) . ? N1 C5 1.357(2) . ? N1 C6 1.435(2) . ? C4 C5 1.364(3) . ? C4 C14 1.491(3) . ? C5 H5 0.96(2) . ? C6 C11 1.382(3) . ? C6 C7 1.390(3) . ? C7 C8 1.390(3) . ? C7 H7 0.97(2) . ? C8 C9 1.391(3) . ? C8 C12 1.512(3) . ? C9 C10 1.394(3) . ? C9 H9 1.01(2) . ? C10 C11 1.391(3) . ? C10 C13 1.505(3) . ? C11 H11 0.95(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 1.02(2) . ? C14 H14B 0.93(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O15 H15 106.6(19) . . ? N3 N2 N1 106.57(15) . . ? N2 N3 C4 109.80(16) . . ? N2 N1 C5 110.68(15) . . ? N2 N1 C6 120.51(15) . . ? C5 N1 C6 128.80(17) . . ? C5 C4 N3 107.61(18) . . ? C5 C4 C14 129.90(18) . . ? N3 C4 C14 122.44(17) . . ? N1 C5 C4 105.34(17) . . ? N1 C5 H5 121.7(14) . . ? C4 C5 H5 133.0(14) . . ? C11 C6 C7 121.77(19) . . ? C11 C6 N1 119.62(17) . . ? C7 C6 N1 118.60(18) . . ? C6 C7 C8 119.38(19) . . ? C6 C7 H7 120.1(14) . . ? C8 C7 H7 120.5(14) . . ? C7 C8 C9 118.65(19) . . ? C7 C8 C12 120.16(18) . . ? C9 C8 C12 121.19(18) . . ? C8 C9 C10 122.09(19) . . ? C8 C9 H9 118.5(14) . . ? C10 C9 H9 119.4(14) . . ? C11 C10 C9 118.64(19) . . ? C11 C10 C13 120.5(2) . . ? C9 C10 C13 120.90(19) . . ? C6 C11 C10 119.43(19) . . ? C6 C11 H11 119.6(13) . . ? C10 C11 H11 121.0(13) . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O15 C14 C4 112.13(17) . . ? O15 C14 H14A 106.3(12) . . ? C4 C14 H14A 108.6(12) . . ? O15 C14 H14B 111.5(14) . . ? C4 C14 H14B 108.1(13) . . ? H14A C14 H14B 110.2(19) . . ? 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 N1 N2 N3 C4 -0.3(2) . . . . ? N3 N2 N1 C5 0.2(2) . . . . ? N3 N2 N1 C6 179.05(17) . . . . ? N2 N3 C4 C5 0.3(2) . . . . ? N2 N3 C4 C14 -177.20(18) . . . . ? N2 N1 C5 C4 0.0(2) . . . . ? C6 N1 C5 C4 -178.75(18) . . . . ? N3 C4 C5 N1 -0.2(2) . . . . ? C14 C4 C5 N1 177.1(2) . . . . ? N2 N1 C6 C11 24.8(3) . . . . ? C5 N1 C6 C11 -156.5(2) . . . . ? N2 N1 C6 C7 -155.35(19) . . . . ? C5 N1 C6 C7 23.3(3) . . . . ? C11 C6 C7 C8 0.5(3) . . . . ? N1 C6 C7 C8 -179.26(18) . . . . ? C6 C7 C8 C9 -1.6(3) . . . . ? C6 C7 C8 C12 178.4(2) . . . . ? C7 C8 C9 C10 0.9(3) . . . . ? C12 C8 C9 C10 -179.1(2) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 C13 -179.3(2) . . . . ? C7 C6 C11 C10 1.2(3) . . . . ? N1 C6 C11 C10 -178.99(18) . . . . ? C9 C10 C11 C6 -1.9(3) . . . . ? C13 C10 C11 C6 178.2(2) . . . . ? C5 C4 C14 O15 -93.8(3) . . . . ? N3 C4 C14 O15 83.1(2) . . . . ? 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 O15 H15 N3 0.87(3) 1.93(3) 2.800(2) 179(3) 3_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.335 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.060