# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Petr Simunek' 'Valerio Bertolasi' 'Antonin Lycka' 'Vladimir Machacek' 'Marketa Peskova' _publ_contact_author_name 'Dr Petr Simunek' _publ_contact_author_address ; Department of Organic Chemistry University of Pardubice Nam. Cs. Legii 565 Pardubice CZ-532 10 ; _publ_contact_author_email P.SIMUNEK@EMAIL.CZ _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Solution and solid state structure and tautomerism of azo coupled enaminone derivatives of benzoylacetone ; data_(I) _database_code_depnum_ccdc_archive 'CCDC 259869' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Br N3 O' _chemical_formula_sum 'C22 H18 Br N3 O' _chemical_formula_weight 420.30 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' Br Br -0.2901 2.4595 '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 9.3969(3) _cell_length_b 10.5034(3) _cell_length_c 10.5516(4) _cell_angle_alpha 71.075(1) _cell_angle_beta 88.902(2) _cell_angle_gamma 81.541(1) _cell_volume 973.97(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 19612 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 30.0 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 2.126 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.700 _exptl_absorpt_correction_T_max 0.813 _exptl_absorpt_process_details ; SORTAV (R.H. Blessing, Acta Crystallogr., 1995, A51, 33) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12849 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.4 _diffrn_reflns_theta_max 30.0 _reflns_number_total 5579 _reflns_number_gt 5075 _reflns_threshold_expression 'I >2sigma(I)' _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), Nardelli (PARST, 1995)' ; _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^)+(0.0315P)^2^+0.4868P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5579 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.003 _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 Br1 Br 0.415275(19) -0.261063(16) 0.642431(17) 0.03358(7) Uani 1 1 d . . . O1 O -0.29187(16) 0.55962(13) 0.64152(14) 0.0398(3) Uani 1 1 d . . . N1 N 0.01013(15) 0.27529(14) 0.48060(14) 0.0266(3) Uani 1 1 d . . . H1 H 0.016(3) 0.337(3) 0.402(3) 0.049(7) Uiso 1 1 d . . . N2 N -0.08692(14) 0.30349(13) 0.56377(13) 0.0248(3) Uani 1 1 d . . . N3 N -0.10248(16) 0.50503(14) 0.30420(14) 0.0296(3) Uani 1 1 d . . . C1 C -0.17841(17) 0.41718(16) 0.52656(16) 0.0255(3) Uani 1 1 d . . . C2 C -0.19695(17) 0.51911(16) 0.39024(17) 0.0270(3) Uani 1 1 d . . . C3 C -0.26051(17) 0.44247(16) 0.64040(17) 0.0276(3) Uani 1 1 d . . . C4 C -0.3290(2) 0.6262(2) 0.3576(2) 0.0370(4) Uani 1 1 d . . . C5 C -0.29968(18) 0.32691(18) 0.75538(17) 0.0299(3) Uani 1 1 d . . . C6 C -0.3087(2) 0.19883(19) 0.7468(2) 0.0358(4) Uani 1 1 d . . . C7 C -0.3470(3) 0.0970(2) 0.8584(3) 0.0513(5) Uani 1 1 d . . . C8 C -0.3755(3) 0.1221(3) 0.9768(3) 0.0634(7) Uani 1 1 d . . . C9 C -0.3714(3) 0.2491(3) 0.9854(2) 0.0640(7) Uani 1 1 d . . . C10 C -0.3341(3) 0.3520(3) 0.8746(2) 0.0479(5) Uani 1 1 d . . . C11 C 0.10137(17) 0.15000(15) 0.52245(16) 0.0250(3) Uani 1 1 d . . . C12 C 0.22029(18) 0.13304(16) 0.44503(16) 0.0271(3) Uani 1 1 d . . . C13 C 0.31170(18) 0.00949(16) 0.48013(17) 0.0280(3) Uani 1 1 d . . . C14 C 0.28493(18) -0.09490(16) 0.59364(17) 0.0272(3) Uani 1 1 d . . . C15 C 0.16823(19) -0.07911(17) 0.67256(18) 0.0304(3) Uani 1 1 d . . . C16 C 0.07567(18) 0.04410(17) 0.63639(17) 0.0287(3) Uani 1 1 d . . . C17 C -0.11448(19) 0.59709(18) 0.16940(17) 0.0319(3) Uani 1 1 d . . . C18 C -0.0645(3) 0.7201(2) 0.1383(2) 0.0440(5) Uani 1 1 d . . . C19 C -0.0669(3) 0.8049(2) 0.0061(2) 0.0499(5) Uani 1 1 d . . . C20 C -0.1187(3) 0.7684(2) -0.0943(2) 0.0474(5) Uani 1 1 d . . . C21 C -0.1675(5) 0.6450(3) -0.0647(2) 0.0784(11) Uani 1 1 d . . . C22 C -0.1641(4) 0.5583(3) 0.0675(2) 0.0692(9) Uani 1 1 d . . . H41 H -0.317(4) 0.708(4) 0.381(3) 0.080(10) Uiso 1 1 d . . . H42 H -0.406(3) 0.590(3) 0.407(3) 0.055(7) Uiso 1 1 d . . . H43 H -0.352(3) 0.650(3) 0.267(3) 0.050(7) Uiso 1 1 d . . . H6 H -0.292(3) 0.183(2) 0.662(2) 0.042(6) Uiso 1 1 d . . . H7 H -0.353(3) 0.008(3) 0.853(3) 0.061(8) Uiso 1 1 d . . . H8 H -0.398(4) 0.049(3) 1.059(3) 0.078(10) Uiso 1 1 d . . . H9 H -0.389(4) 0.274(3) 1.065(3) 0.080(10) Uiso 1 1 d . . . H10 H -0.332(3) 0.439(3) 0.877(3) 0.051(7) Uiso 1 1 d . . . H12 H 0.241(2) 0.208(2) 0.371(2) 0.032(5) Uiso 1 1 d . . . H13 H 0.396(2) -0.002(2) 0.423(2) 0.036(6) Uiso 1 1 d . . . H15 H 0.149(3) -0.155(3) 0.753(3) 0.046(6) Uiso 1 1 d . . . H16 H -0.006(3) 0.056(2) 0.686(2) 0.038(6) Uiso 1 1 d . . . H18 H -0.030(3) 0.747(3) 0.211(3) 0.061(8) Uiso 1 1 d . . . H19 H -0.029(3) 0.888(3) -0.017(3) 0.072(9) Uiso 1 1 d . . . H20 H -0.121(3) 0.831(3) -0.190(3) 0.059(8) Uiso 1 1 d . . . H21 H -0.201(4) 0.615(4) -0.137(4) 0.102(12) Uiso 1 1 d . . . H22 H -0.200(4) 0.471(4) 0.088(4) 0.094(11) 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 Br1 0.03607(10) 0.02456(9) 0.03759(11) -0.01011(7) 0.00036(7) 0.00356(6) O1 0.0495(8) 0.0273(6) 0.0408(7) -0.0133(5) 0.0057(6) 0.0041(5) N1 0.0280(6) 0.0229(6) 0.0264(6) -0.0059(5) 0.0023(5) -0.0007(5) N2 0.0249(6) 0.0240(6) 0.0262(6) -0.0094(5) 0.0004(5) -0.0028(5) N3 0.0313(7) 0.0274(6) 0.0267(7) -0.0045(5) 0.0001(5) -0.0032(5) C1 0.0258(7) 0.0237(7) 0.0266(7) -0.0083(6) -0.0004(6) -0.0015(5) C2 0.0260(7) 0.0242(7) 0.0297(8) -0.0075(6) -0.0027(6) -0.0025(6) C3 0.0266(7) 0.0263(7) 0.0290(8) -0.0092(6) -0.0006(6) 0.0001(6) C4 0.0323(9) 0.0360(9) 0.0343(9) -0.0045(7) -0.0036(7) 0.0062(7) C5 0.0277(8) 0.0335(8) 0.0272(8) -0.0084(6) 0.0010(6) -0.0036(6) C6 0.0329(9) 0.0334(9) 0.0388(10) -0.0085(7) 0.0055(7) -0.0064(7) C7 0.0513(12) 0.0402(11) 0.0558(13) -0.0036(10) 0.0117(10) -0.0150(9) C8 0.0694(16) 0.0689(17) 0.0418(12) 0.0029(11) 0.0103(11) -0.0284(14) C9 0.0800(18) 0.087(2) 0.0308(11) -0.0185(12) 0.0153(11) -0.0335(16) C10 0.0588(13) 0.0563(13) 0.0354(10) -0.0199(9) 0.0094(9) -0.0193(11) C11 0.0259(7) 0.0225(7) 0.0267(7) -0.0087(6) 0.0001(6) -0.0023(5) C12 0.0297(7) 0.0251(7) 0.0263(7) -0.0081(6) 0.0031(6) -0.0043(6) C13 0.0293(8) 0.0263(7) 0.0296(8) -0.0114(6) 0.0029(6) -0.0024(6) C14 0.0282(7) 0.0219(7) 0.0315(8) -0.0104(6) -0.0009(6) 0.0005(6) C15 0.0324(8) 0.0249(7) 0.0309(8) -0.0052(6) 0.0045(6) -0.0037(6) C16 0.0289(8) 0.0253(7) 0.0302(8) -0.0073(6) 0.0057(6) -0.0028(6) C17 0.0339(8) 0.0307(8) 0.0283(8) -0.0053(6) 0.0010(6) -0.0054(7) C18 0.0604(13) 0.0350(9) 0.0340(10) -0.0033(8) -0.0139(9) -0.0153(9) C19 0.0675(14) 0.0373(10) 0.0400(11) 0.0013(8) -0.0127(10) -0.0226(10) C20 0.0634(14) 0.0450(11) 0.0300(9) -0.0016(8) 0.0008(9) -0.0200(10) C21 0.148(3) 0.0653(17) 0.0300(11) -0.0078(11) -0.0058(14) -0.059(2) C22 0.128(3) 0.0530(14) 0.0327(11) -0.0057(10) -0.0020(13) -0.0510(16) _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 Br1 C14 1.9036(16) . ? O1 C3 1.226(2) . ? N1 N2 1.3221(19) . ? N1 C11 1.403(2) . ? N1 H1 0.88(3) . ? N2 C1 1.314(2) . ? N3 C2 1.285(2) . ? N3 C17 1.433(2) . ? C1 C2 1.484(2) . ? C1 C3 1.490(2) . ? C2 C4 1.509(2) . ? C3 C5 1.497(2) . ? C4 H41 0.99(4) . ? C4 H42 0.94(3) . ? C4 H43 0.93(3) . ? C5 C10 1.390(3) . ? C5 C6 1.392(3) . ? C6 C7 1.393(3) . ? C6 H6 0.96(2) . ? C7 C8 1.372(4) . ? C7 H7 0.96(3) . ? C8 C9 1.373(4) . ? C8 H8 0.99(3) . ? C9 C10 1.390(3) . ? C9 H9 0.96(3) . ? C10 H10 0.93(3) . ? C11 C16 1.393(2) . ? C11 C12 1.396(2) . ? C12 C13 1.390(2) . ? C12 H12 0.95(2) . ? C13 C14 1.385(2) . ? C13 H13 1.01(2) . ? C14 C15 1.387(2) . ? C15 C16 1.392(2) . ? C15 H15 0.99(2) . ? C16 H16 0.94(2) . ? C17 C18 1.377(3) . ? C17 C22 1.378(3) . ? C18 C19 1.388(3) . ? C18 H18 0.97(3) . ? C19 C20 1.358(3) . ? C19 H19 0.95(3) . ? C20 C21 1.376(3) . ? C20 H20 1.01(3) . ? C21 C22 1.395(3) . ? C21 H21 0.98(4) . ? C22 H22 0.98(4) . ? 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 C11 118.88(13) . . ? N2 N1 H1 118.5(17) . . ? C11 N1 H1 122.6(17) . . ? C1 N2 N1 120.83(14) . . ? C2 N3 C17 120.63(15) . . ? N2 C1 C2 126.47(14) . . ? N2 C1 C3 112.76(14) . . ? C2 C1 C3 120.65(14) . . ? N3 C2 C1 117.10(14) . . ? N3 C2 C4 123.84(15) . . ? C1 C2 C4 118.91(15) . . ? O1 C3 C1 119.18(15) . . ? O1 C3 C5 119.81(15) . . ? C1 C3 C5 120.96(14) . . ? C2 C4 H41 113(2) . . ? C2 C4 H42 109.0(16) . . ? H41 C4 H42 107(2) . . ? C2 C4 H43 108.5(16) . . ? H41 C4 H43 111(2) . . ? H42 C4 H43 109(2) . . ? C10 C5 C6 118.97(18) . . ? C10 C5 C3 117.54(17) . . ? C6 C5 C3 123.43(16) . . ? C5 C6 C7 119.9(2) . . ? C5 C6 H6 119.2(14) . . ? C7 C6 H6 120.9(14) . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.5(17) . . ? C6 C7 H7 120.2(17) . . ? C7 C8 C9 120.4(2) . . ? C7 C8 H8 122(2) . . ? C9 C8 H8 117.8(19) . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 125(2) . . ? C10 C9 H9 115(2) . . ? C5 C10 C9 120.5(2) . . ? C5 C10 H10 117.6(16) . . ? C9 C10 H10 121.9(16) . . ? C16 C11 C12 120.11(15) . . ? C16 C11 N1 122.13(14) . . ? C12 C11 N1 117.77(14) . . ? C13 C12 C11 119.98(15) . . ? C13 C12 H12 120.2(13) . . ? C11 C12 H12 119.8(13) . . ? C14 C13 C12 119.30(15) . . ? C14 C13 H13 121.3(13) . . ? C12 C13 H13 119.4(13) . . ? C13 C14 C15 121.41(15) . . ? C13 C14 Br1 118.40(12) . . ? C15 C14 Br1 120.18(12) . . ? C14 C15 C16 119.26(15) . . ? C14 C15 H15 120.8(14) . . ? C16 C15 H15 119.9(14) . . ? C15 C16 C11 119.93(15) . . ? C15 C16 H16 121.0(14) . . ? C11 C16 H16 119.0(14) . . ? C18 C17 C22 119.11(18) . . ? C18 C17 N3 120.39(16) . . ? C22 C17 N3 120.24(17) . . ? C17 C18 C19 120.27(19) . . ? C17 C18 H18 118.8(16) . . ? C19 C18 H18 120.9(16) . . ? C20 C19 C18 120.81(19) . . ? C20 C19 H19 118.4(19) . . ? C18 C19 H19 120.7(19) . . ? C19 C20 C21 119.5(2) . . ? C19 C20 H20 120.4(16) . . ? C21 C20 H20 120.1(16) . . ? C20 C21 C22 120.2(2) . . ? C20 C21 H21 120(2) . . ? C22 C21 H21 119(2) . . ? C17 C22 C21 120.1(2) . . ? C17 C22 H22 120(2) . . ? C21 C22 H22 120(2) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.349 _refine_diff_density_min -0.748 _refine_diff_density_rms 0.062 #===END data_(II) _database_code_depnum_ccdc_archive 'CCDC 259870' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N4 O, 1/2(C7 H8)' _chemical_formula_sum 'C21.50 H24 N4 O' _chemical_formula_weight 354.45 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 'C 2/c' 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' '-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 25.8225(3) _cell_length_b 10.7493(2) _cell_length_c 15.6270(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.694(1) _cell_angle_gamma 90.00 _cell_volume 3840.7(1) _cell_formula_units_Z 8 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5167 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 28.0 _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 0.078 _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 150 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23700 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.6 _diffrn_reflns_theta_max 28.0 _reflns_number_total 4585 _reflns_number_gt 4083 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)' ; _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^)+(0.0256P)^2^+4.0016P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4585 _refine_ls_number_parameters 336 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.80296(5) 1.04580(10) 0.83994(8) 0.0382(3) Uani 1 1 d . . . N1 N 0.67866(5) 0.84191(11) 0.92894(9) 0.0303(3) Uani 1 1 d . . . H1 H 0.663(5) 0.762(11) 0.886(9) 0.036 Uiso 0.15(3) 1 d P . . N2 N 0.71883(5) 0.92096(11) 0.94161(9) 0.0298(3) Uani 1 1 d . . . N3 N 0.70054(6) 0.72839(12) 0.80015(10) 0.0345(3) Uani 1 1 d . . . H31 H 0.6791(10) 0.737(2) 0.8350(17) 0.041 Uiso 0.85(3) 1 d P . . N4 N 0.55574(6) 0.93554(14) 1.13993(11) 0.0424(3) Uani 1 1 d . . . C1 C 0.74818(6) 0.91078(13) 0.88694(10) 0.0292(3) Uani 1 1 d . . . C2 C 0.74103(6) 0.81528(13) 0.82067(10) 0.0298(3) Uani 1 1 d . . . C3 C 0.78860(6) 1.01361(13) 0.90222(10) 0.0306(3) Uani 1 1 d . . . C4 C 0.77892(7) 0.80270(16) 0.77211(12) 0.0351(3) Uani 1 1 d . . . C5 C 0.81440(6) 1.08271(14) 0.99620(11) 0.0312(3) Uani 1 1 d . . . C6 C 0.83060(7) 1.02126(16) 1.08342(11) 0.0352(3) Uani 1 1 d . . . C7 C 0.85904(8) 1.08555(18) 1.17008(12) 0.0423(4) Uani 1 1 d . . . C8 C 0.87041(8) 1.21163(18) 1.17025(14) 0.0463(4) Uani 1 1 d . . . C9 C 0.85428(8) 1.27307(17) 1.08398(14) 0.0472(4) Uani 1 1 d . . . C10 C 0.82688(7) 1.20884(15) 0.99697(13) 0.0394(4) Uani 1 1 d . . . C11 C 0.65130(6) 0.86576(13) 0.98797(10) 0.0296(3) Uani 1 1 d . . . C12 C 0.66928(7) 0.95752(14) 1.05947(11) 0.0326(3) Uani 1 1 d . . . C13 C 0.63821(7) 0.97982(15) 1.11011(11) 0.0345(3) Uani 1 1 d . . . C14 C 0.58768(6) 0.91054(14) 1.09137(11) 0.0323(3) Uani 1 1 d . . . C15 C 0.57160(7) 0.81455(15) 1.02272(12) 0.0356(3) Uani 1 1 d . . . C16 C 0.60311(7) 0.79342(15) 0.97232(12) 0.0348(3) Uani 1 1 d . . . C17 C 0.57048(10) 1.0409(2) 1.20407(16) 0.0521(5) Uani 1 1 d . . . C18 C 0.50006(8) 0.8747(2) 1.11163(15) 0.0465(4) Uani 1 1 d . . . C1A C 0.98619(10) 1.0423(3) 0.9054(2) 0.0829(9) Uani 1 1 d . . . C2A C 0.95049(11) 1.0698(3) 0.9478(3) 0.0829(9) Uani 1 1 d . . . H2A H 0.9159(14) 1.122(3) 0.909(2) 0.104(10) Uiso 1 1 d . . . C3A C 0.96416(10) 1.0295(3) 1.0401(3) 0.0804(9) Uani 1 1 d . . . H3A H 0.9383(12) 1.055(2) 1.0672(19) 0.085(8) Uiso 1 1 d . . . C4A C 0.9722(2) 1.1039(6) 0.7965(4) 0.0820(16) Uani 0.50 1 d P . . H4A1 H 0.9332 1.1372 0.7656 0.098 Uiso 0.50 1 calc PR . . H4A2 H 0.9757 1.0402 0.7565 0.098 Uiso 0.50 1 calc PR . . H4A3 H 0.9997 1.1692 0.8059 0.098 Uiso 0.50 1 calc PR . . H32 H 0.6970(9) 0.667(2) 0.7568(15) 0.058(6) Uiso 1 1 d . . . H41 H 0.8208(9) 0.8211(17) 0.8172(14) 0.044(5) Uiso 1 1 d . . . H42 H 0.7655(8) 0.8613(19) 0.7156(14) 0.048(5) Uiso 1 1 d . . . H43 H 0.7746(9) 0.719(2) 0.7456(15) 0.055(6) Uiso 1 1 d . . . H6 H 0.8223(8) 0.9320(18) 1.0819(13) 0.042(5) Uiso 1 1 d . . . H7 H 0.8714(9) 1.0403(19) 1.2324(15) 0.053(6) Uiso 1 1 d . . . H8 H 0.8923(9) 1.256(2) 1.2354(16) 0.060(6) Uiso 1 1 d . . . H9 H 0.8609(10) 1.362(2) 1.0830(16) 0.063(6) Uiso 1 1 d . . . H10 H 0.8153(9) 1.252(2) 0.9313(15) 0.053(6) Uiso 1 1 d . . . H12 H 0.7047(8) 1.0084(18) 1.0711(13) 0.042(5) Uiso 1 1 d . . . H13 H 0.6523(8) 1.0494(18) 1.1610(13) 0.045(5) Uiso 1 1 d . . . H15 H 0.5365(8) 0.7613(17) 1.0080(13) 0.041(5) Uiso 1 1 d . . . H16 H 0.5911(8) 0.7252(18) 0.9234(14) 0.043(5) Uiso 1 1 d . . . H171 H 0.5685(11) 1.122(3) 1.1682(18) 0.078(8) Uiso 1 1 d . . . H172 H 0.5427(11) 1.047(2) 1.2336(17) 0.078(7) Uiso 1 1 d . . . H173 H 0.6112(13) 1.036(3) 1.258(2) 0.089(9) Uiso 1 1 d . . . H181 H 0.4728(11) 0.882(2) 1.0375(18) 0.075(7) Uiso 1 1 d . . . H182 H 0.5069(11) 0.783(3) 1.1272(18) 0.077(8) Uiso 1 1 d . . . H183 H 0.4836(13) 0.906(3) 1.151(2) 0.100(9) 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 O1 0.0486(6) 0.0359(6) 0.0379(6) 0.0052(5) 0.0266(5) -0.0038(5) N1 0.0339(6) 0.0281(6) 0.0331(6) -0.0002(5) 0.0190(5) -0.0016(5) N2 0.0318(6) 0.0286(6) 0.0321(6) 0.0027(5) 0.0174(5) 0.0008(5) N3 0.0414(7) 0.0300(6) 0.0383(7) -0.0054(5) 0.0238(6) -0.0044(5) N4 0.0427(7) 0.0490(8) 0.0474(8) -0.0130(6) 0.0310(7) -0.0098(6) C1 0.0333(7) 0.0275(7) 0.0302(7) 0.0028(5) 0.0177(6) 0.0008(5) C2 0.0327(7) 0.0286(7) 0.0294(7) 0.0050(5) 0.0155(6) 0.0032(5) C3 0.0342(7) 0.0275(7) 0.0329(7) 0.0049(5) 0.0180(6) 0.0025(6) C4 0.0393(8) 0.0364(8) 0.0351(8) -0.0003(6) 0.0220(7) 0.0012(6) C5 0.0322(7) 0.0298(7) 0.0357(7) 0.0008(6) 0.0192(6) -0.0013(6) C6 0.0379(8) 0.0373(8) 0.0346(8) 0.0016(6) 0.0205(7) -0.0019(6) C7 0.0426(9) 0.0541(10) 0.0346(8) -0.0017(7) 0.0216(7) -0.0047(8) C8 0.0450(9) 0.0537(10) 0.0438(9) -0.0154(8) 0.0237(8) -0.0117(8) C9 0.0532(10) 0.0372(9) 0.0526(11) -0.0096(8) 0.0258(9) -0.0108(8) C10 0.0441(9) 0.0319(8) 0.0431(9) 0.0001(7) 0.0209(7) -0.0047(7) C11 0.0327(7) 0.0285(7) 0.0308(7) 0.0005(5) 0.0176(6) -0.0006(5) C12 0.0336(7) 0.0337(7) 0.0333(7) -0.0027(6) 0.0178(6) -0.0048(6) C13 0.0359(7) 0.0364(8) 0.0331(7) -0.0056(6) 0.0177(6) -0.0046(6) C14 0.0334(7) 0.0354(7) 0.0321(7) -0.0003(6) 0.0186(6) -0.0008(6) C15 0.0348(7) 0.0363(8) 0.0412(8) -0.0047(6) 0.0223(7) -0.0070(6) C16 0.0376(8) 0.0335(7) 0.0370(8) -0.0059(6) 0.0204(7) -0.0059(6) C17 0.0605(12) 0.0547(11) 0.0585(12) -0.0186(9) 0.0422(11) -0.0110(9) C18 0.0377(9) 0.0600(12) 0.0498(10) -0.0064(9) 0.0269(8) -0.0066(8) C1A 0.0501(12) 0.0895(18) 0.110(2) -0.0559(16) 0.0377(13) -0.0299(12) C2A 0.0417(12) 0.0822(18) 0.120(2) -0.0469(18) 0.0339(14) -0.0167(12) C3A 0.0514(13) 0.0847(18) 0.118(2) -0.0583(17) 0.0507(15) -0.0244(12) C4A 0.075(3) 0.099(4) 0.065(3) -0.021(3) 0.027(3) -0.042(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2410(17) . ? N1 N2 1.2832(17) . ? N1 C11 1.4219(18) . ? N1 H1 1.04(13) . ? N2 C1 1.3849(17) . ? N3 C2 1.3254(19) . ? N3 H31 0.94(2) . ? N3 H32 0.92(2) . ? N4 C14 1.3818(18) . ? N4 C17 1.441(2) . ? N4 C18 1.449(2) . ? C1 C2 1.408(2) . ? C1 C3 1.462(2) . ? C2 C4 1.497(2) . ? C3 C5 1.498(2) . ? C4 H41 1.00(2) . ? C4 H42 1.01(2) . ? C4 H43 0.98(2) . ? C5 C10 1.392(2) . ? C5 C6 1.393(2) . ? C6 C7 1.388(2) . ? C6 H6 0.981(19) . ? C7 C8 1.386(3) . ? C7 H7 1.00(2) . ? C8 C9 1.380(3) . ? C8 H8 1.03(2) . ? C9 C10 1.390(2) . ? C9 H9 0.97(2) . ? C10 H10 1.03(2) . ? C11 C16 1.389(2) . ? C11 C12 1.398(2) . ? C12 C13 1.385(2) . ? C12 H12 1.008(19) . ? C13 C14 1.410(2) . ? C13 H13 1.027(19) . ? C14 C15 1.405(2) . ? C15 C16 1.389(2) . ? C15 H15 1.003(19) . ? C16 H16 0.999(19) . ? C17 H171 1.02(3) . ? C17 H172 1.02(3) . ? C17 H173 1.00(3) . ? C18 H181 1.04(2) . ? C18 H182 1.01(3) . ? C18 H183 0.96(3) . ? C1A C2A 1.395(4) . ? C1A C3A 1.396(4) 5_777 ? C1A C4A 1.701(6) . ? C2A C3A 1.385(4) . ? C2A H2A 0.99(3) . ? C3A C1A 1.396(4) 5_777 ? C3A H3A 0.98(3) . ? C4A H4A1 0.9600 . ? C4A H4A2 0.9600 . ? C4A H4A3 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 N2 N1 C11 112.98(12) . . ? N2 N1 H1 133(7) . . ? C11 N1 H1 114(7) . . ? N1 N2 C1 119.18(12) . . ? C2 N3 H31 113.8(14) . . ? C2 N3 H32 118.8(13) . . ? H31 N3 H32 127.3(19) . . ? C14 N4 C17 120.18(14) . . ? C14 N4 C18 120.36(14) . . ? C17 N4 C18 118.07(15) . . ? N2 C1 C2 126.08(13) . . ? N2 C1 C3 113.16(12) . . ? C2 C1 C3 120.74(12) . . ? N3 C2 C1 120.71(13) . . ? N3 C2 C4 116.21(13) . . ? C1 C2 C4 123.05(13) . . ? O1 C3 C1 122.25(14) . . ? O1 C3 C5 118.16(13) . . ? C1 C3 C5 119.58(12) . . ? C2 C4 H41 111.9(11) . . ? C2 C4 H42 110.4(11) . . ? H41 C4 H42 108.3(15) . . ? C2 C4 H43 109.0(12) . . ? H41 C4 H43 110.9(16) . . ? H42 C4 H43 106.3(16) . . ? C10 C5 C6 119.37(15) . . ? C10 C5 C3 119.15(14) . . ? C6 C5 C3 121.26(13) . . ? C7 C6 C5 120.06(16) . . ? C7 C6 H6 121.4(11) . . ? C5 C6 H6 118.5(11) . . ? C8 C7 C6 120.27(16) . . ? C8 C7 H7 120.1(12) . . ? C6 C7 H7 119.6(12) . . ? C9 C8 C7 119.89(16) . . ? C9 C8 H8 121.5(13) . . ? C7 C8 H8 118.6(12) . . ? C8 C9 C10 120.22(17) . . ? C8 C9 H9 120.7(13) . . ? C10 C9 H9 119.1(13) . . ? C9 C10 C5 120.17(16) . . ? C9 C10 H10 122.1(12) . . ? C5 C10 H10 117.7(12) . . ? C16 C11 C12 118.24(13) . . ? C16 C11 N1 117.35(13) . . ? C12 C11 N1 124.40(13) . . ? C13 C12 C11 120.89(14) . . ? C13 C12 H12 121.5(11) . . ? C11 C12 H12 117.6(10) . . ? C12 C13 C14 121.06(14) . . ? C12 C13 H13 118.5(11) . . ? C14 C13 H13 120.4(11) . . ? N4 C14 C15 121.47(14) . . ? N4 C14 C13 120.94(14) . . ? C15 C14 C13 117.59(13) . . ? C16 C15 C14 120.66(14) . . ? C16 C15 H15 118.8(11) . . ? C14 C15 H15 120.6(10) . . ? C15 C16 C11 121.43(14) . . ? C15 C16 H16 119.9(11) . . ? C11 C16 H16 118.7(11) . . ? N4 C17 H171 110.9(14) . . ? N4 C17 H172 110.4(14) . . ? H171 C17 H172 109(2) . . ? N4 C17 H173 112.1(16) . . ? H171 C17 H173 106(2) . . ? H172 C17 H173 108(2) . . ? N4 C18 H181 111.4(14) . . ? N4 C18 H182 109.2(14) . . ? H181 C18 H182 107(2) . . ? N4 C18 H183 108.6(18) . . ? H181 C18 H183 114(2) . . ? H182 C18 H183 106(2) . . ? C2A C1A C3A 116.7(3) . 5_777 ? C2A C1A C4A 120.8(3) . . ? C3A C1A C4A 122.3(3) 5_777 . ? C3A C2A C1A 121.6(3) . . ? C3A C2A H2A 122.7(18) . . ? C1A C2A H2A 115.7(19) . . ? C2A C3A C1A 121.7(2) . 5_777 ? C2A C3A H3A 117.8(16) . . ? C1A C3A H3A 120.4(16) 5_777 . ? C1A C4A H4A1 109.5 . . ? C1A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C1A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.211 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.037 #===END data_(III) _database_code_depnum_ccdc_archive 'CCDC 259871' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 N3 O' _chemical_formula_sum 'C17 H17 N3 O' _chemical_formula_weight 279.34 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.7502(1) _cell_length_b 29.873(1) _cell_length_c 9.1184(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.110(2) _cell_angle_gamma 90.00 _cell_volume 1536.98(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 3370 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.45 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.077 _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 150 _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16607 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0987 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 27.5 _reflns_number_total 3481 _reflns_number_gt 1828 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0476P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3481 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7677(3) 0.22030(5) -0.22584(17) 0.0443(4) Uani 1 1 d . . . N1 N 0.5008(3) 0.11873(6) 0.08726(19) 0.0352(5) Uani 1 1 d . . . H1 H 0.42(3) 0.145(6) 0.135(13) 0.042 Uiso 0.18(5) 1 d P . . N2 N 0.6414(3) 0.13190(6) 0.00255(19) 0.0346(5) Uani 1 1 d . . . N3 N 0.3579(3) 0.20216(8) 0.1046(2) 0.0376(5) Uani 1 1 d . . . H31 H 0.340(6) 0.1709(15) 0.127(3) 0.045 Uiso 0.82(5) 1 d P . . C1 C 0.6316(4) 0.17608(7) -0.0434(2) 0.0330(5) Uani 1 1 d . . . C2 C 0.5073(3) 0.21056(7) 0.0132(2) 0.0330(5) Uani 1 1 d . . . C3 C 0.7770(4) 0.18488(8) -0.1567(2) 0.0357(5) Uani 1 1 d . . . C4 C 0.5395(4) 0.25874(7) -0.0184(2) 0.0321(5) Uani 1 1 d . . . C5 C 0.3481(4) 0.28333(8) -0.0922(2) 0.0375(5) Uani 1 1 d . . . C6 C 0.3746(5) 0.32850(8) -0.1203(3) 0.0454(6) Uani 1 1 d . . . C7 C 0.5904(5) 0.34899(9) -0.0729(3) 0.0464(7) Uani 1 1 d . . . C8 C 0.7813(5) 0.32481(8) 0.0039(3) 0.0458(7) Uani 1 1 d . . . C9 C 0.7559(4) 0.27978(8) 0.0312(3) 0.0396(6) Uani 1 1 d . . . C10 C 0.9395(5) 0.14828(10) -0.1909(3) 0.0468(7) Uani 1 1 d . . . C11 C 0.5423(4) 0.07362(7) 0.1371(2) 0.0344(5) Uani 1 1 d . . . C12 C 0.3899(4) 0.05620(8) 0.2231(3) 0.0464(7) Uani 1 1 d . . . C13 C 0.4213(5) 0.01334(8) 0.2802(3) 0.0488(7) Uani 1 1 d . . . C14 C 0.6041(4) -0.01360(8) 0.2540(2) 0.0438(6) Uani 1 1 d . . . C15 C 0.7540(4) 0.00392(8) 0.1660(3) 0.0496(7) Uani 1 1 d . . . C16 C 0.7265(4) 0.04671(8) 0.1089(3) 0.0452(6) Uani 1 1 d . . . C17 C 0.6379(7) -0.06009(10) 0.3160(4) 0.0632(9) Uani 1 1 d . . . H32 H 0.305(4) 0.2259(8) 0.152(3) 0.053(7) Uiso 1 1 d . . . H5 H 0.195(4) 0.2677(7) -0.128(2) 0.042(6) Uiso 1 1 d . . . H6 H 0.236(4) 0.3457(7) -0.172(3) 0.055(7) Uiso 1 1 d . . . H7 H 0.602(4) 0.3800(8) -0.094(2) 0.044(6) Uiso 1 1 d . . . H8 H 0.935(4) 0.3390(7) 0.041(2) 0.051(7) Uiso 1 1 d . . . H9 H 0.883(3) 0.2629(7) 0.081(2) 0.030(6) Uiso 1 1 d . . . H101 H 0.861(5) 0.1241(10) -0.238(3) 0.089(11) Uiso 1 1 d . . . H102 H 1.053(4) 0.1611(8) -0.249(3) 0.072(8) Uiso 1 1 d . . . H103 H 1.045(4) 0.1350(9) -0.102(3) 0.072(9) Uiso 1 1 d . . . H12 H 0.257(4) 0.0759(7) 0.234(2) 0.050(7) Uiso 1 1 d . . . H13 H 0.311(4) 0.0001(8) 0.341(3) 0.074(8) Uiso 1 1 d . . . H15 H 0.888(4) -0.0151(8) 0.146(3) 0.070(8) Uiso 1 1 d . . . H16 H 0.828(4) 0.0599(7) 0.044(2) 0.054(7) Uiso 1 1 d . . . H171 H 0.535(5) -0.0657(9) 0.390(3) 0.084(9) Uiso 1 1 d . . . H172 H 0.611(5) -0.0825(11) 0.248(4) 0.089(11) Uiso 1 1 d . . . H173 H 0.806(6) -0.0699(11) 0.347(4) 0.115(13) 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 O1 0.0550(10) 0.0418(10) 0.0402(10) 0.0033(8) 0.0193(8) -0.0028(8) N1 0.0400(11) 0.0339(11) 0.0342(11) -0.0024(9) 0.0137(9) -0.0023(9) N2 0.0351(10) 0.0380(11) 0.0316(10) 0.0003(8) 0.0087(9) -0.0007(9) N3 0.0397(11) 0.0357(12) 0.0412(12) 0.0010(10) 0.0176(10) 0.0031(10) C1 0.0348(12) 0.0317(13) 0.0338(12) -0.0009(10) 0.0102(10) 0.0001(10) C2 0.0300(11) 0.0402(14) 0.0279(12) 0.0000(10) 0.0034(10) 0.0014(10) C3 0.0367(13) 0.0397(14) 0.0310(13) -0.0018(11) 0.0073(11) -0.0059(11) C4 0.0344(13) 0.0326(13) 0.0318(13) -0.0019(10) 0.0124(10) -0.0025(10) C5 0.0399(14) 0.0403(14) 0.0322(13) 0.0016(11) 0.0065(11) -0.0014(12) C6 0.0558(17) 0.0428(16) 0.0384(15) 0.0055(12) 0.0105(13) 0.0021(14) C7 0.0684(19) 0.0340(15) 0.0421(15) 0.0026(12) 0.0243(14) -0.0050(14) C8 0.0475(16) 0.0461(16) 0.0486(16) -0.0077(13) 0.0215(14) -0.0129(14) C9 0.0349(14) 0.0409(15) 0.0447(15) -0.0046(12) 0.0118(12) 0.0002(12) C10 0.0495(17) 0.0484(17) 0.0489(18) -0.0026(14) 0.0256(15) 0.0038(14) C11 0.0389(13) 0.0309(13) 0.0339(13) -0.0027(10) 0.0086(11) -0.0017(10) C12 0.0570(16) 0.0366(15) 0.0526(16) -0.0021(12) 0.0282(13) 0.0038(12) C13 0.0653(17) 0.0390(15) 0.0479(16) 0.0006(12) 0.0257(14) -0.0030(13) C14 0.0586(16) 0.0324(14) 0.0398(14) -0.0035(11) 0.0077(13) -0.0015(12) C15 0.0510(15) 0.0413(16) 0.0587(17) 0.0024(13) 0.0160(14) 0.0111(13) C16 0.0422(14) 0.0457(16) 0.0511(15) 0.0052(12) 0.0176(12) 0.0051(12) C17 0.093(3) 0.0375(18) 0.063(2) 0.0051(15) 0.0226(19) 0.0076(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.228(3) . ? N1 N2 1.283(2) . ? N1 C11 1.428(3) . ? N1 H1 1.07(19) . ? N2 C1 1.383(3) . ? N3 C2 1.331(3) . ? N3 H31 0.96(4) . ? N3 H32 0.92(2) . ? C1 C2 1.407(3) . ? C1 C3 1.472(3) . ? C2 C4 1.487(3) . ? C3 C10 1.510(3) . ? C4 C5 1.385(3) . ? C4 C9 1.390(3) . ? C5 C6 1.387(3) . ? C5 H5 0.99(2) . ? C6 C7 1.376(3) . ? C6 H6 0.99(2) . ? C7 C8 1.386(3) . ? C7 H7 0.95(2) . ? C8 C9 1.381(3) . ? C8 H8 0.98(2) . ? C9 H9 0.93(2) . ? C10 H101 0.91(3) . ? C10 H102 0.99(3) . ? C10 H103 0.99(3) . ? C11 C12 1.385(3) . ? C11 C16 1.392(3) . ? C12 C13 1.381(3) . ? C12 H12 0.99(2) . ? C13 C14 1.381(3) . ? C13 H13 1.00(2) . ? C14 C15 1.388(3) . ? C14 C17 1.498(3) . ? C15 C16 1.378(3) . ? C15 H15 1.00(2) . ? C16 H16 0.99(2) . ? C17 H171 1.00(3) . ? C17 H172 0.90(3) . ? C17 H173 1.00(4) . ? 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 C11 113.24(17) . . ? N2 N1 H1 114(6) . . ? C11 N1 H1 129(7) . . ? N1 N2 C1 118.78(17) . . ? C2 N3 H31 114.8(19) . . ? C2 N3 H32 117.9(14) . . ? H31 N3 H32 126(2) . . ? N2 C1 C2 125.54(17) . . ? N2 C1 C3 112.80(17) . . ? C2 C1 C3 121.60(19) . . ? N3 C2 C1 121.8(2) . . ? N3 C2 C4 115.05(18) . . ? C1 C2 C4 123.12(17) . . ? O1 C3 C1 122.7(2) . . ? O1 C3 C10 119.06(19) . . ? C1 C3 C10 118.3(2) . . ? C5 C4 C9 119.7(2) . . ? C5 C4 C2 119.40(19) . . ? C9 C4 C2 120.8(2) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 118.7(12) . . ? C6 C5 H5 121.2(12) . . ? C7 C6 C5 119.9(3) . . ? C7 C6 H6 120.9(13) . . ? C5 C6 H6 119.1(13) . . ? C6 C7 C8 120.3(3) . . ? C6 C7 H7 117.8(14) . . ? C8 C7 H7 121.9(14) . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 118.5(14) . . ? C7 C8 H8 121.6(13) . . ? C8 C9 C4 120.0(3) . . ? C8 C9 H9 121.0(12) . . ? C4 C9 H9 118.9(12) . . ? C3 C10 H101 113.5(18) . . ? C3 C10 H102 109.0(14) . . ? H101 C10 H102 112(2) . . ? C3 C10 H103 115.1(14) . . ? H101 C10 H103 104(2) . . ? H102 C10 H103 103(2) . . ? C12 C11 C16 118.3(2) . . ? C12 C11 N1 116.70(18) . . ? C16 C11 N1 124.96(18) . . ? C13 C12 C11 120.7(2) . . ? C13 C12 H12 124.1(12) . . ? C11 C12 H12 115.1(12) . . ? C14 C13 C12 121.6(2) . . ? C14 C13 H13 116.8(14) . . ? C12 C13 H13 121.6(14) . . ? C13 C14 C15 117.3(2) . . ? C13 C14 C17 121.5(2) . . ? C15 C14 C17 121.2(2) . . ? C16 C15 C14 122.0(2) . . ? C16 C15 H15 119.7(14) . . ? C14 C15 H15 118.3(14) . . ? C15 C16 C11 120.1(2) . . ? C15 C16 H16 123.9(13) . . ? C11 C16 H16 115.9(13) . . ? C14 C17 H171 111.2(16) . . ? C14 C17 H172 116(2) . . ? H171 C17 H172 107(2) . . ? C14 C17 H173 115.4(19) . . ? H171 C17 H173 115(2) . . ? H172 C17 H173 90(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.195 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.046