# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Lei Yang' _publ_contact_author_email lyang@licp.cas.cn loop_ _publ_author_name 'Feng Han' 'Lei Yang' 'Zhen Li' 'Chungu Xia' # Attachment '- 2ef.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 836789' #TrackingRef '- 2ef.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 N4 O' _chemical_formula_weight 292.34 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 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.203(2) _cell_length_b 13.362(5) _cell_length_c 18.973(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.802(10) _cell_angle_gamma 90.00 _cell_volume 1505.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9752 _exptl_absorpt_correction_T_max 0.9793 _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_type 'Bruker APEX II area detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9338 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.0811 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2599 _reflns_number_gt 1745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0858P)^2^+0.1795P] 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_number_reflns 2599 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1850 _refine_ls_wR_factor_gt 0.1615 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.8438(4) 0.84854(15) 0.55982(12) 0.0868(7) Uani 1 1 d . . . N1 N 0.8033(3) 0.53918(14) 0.53471(11) 0.0573(6) Uani 1 1 d . . . N2 N 0.9022(4) 0.62077(15) 0.52173(12) 0.0584(6) Uani 1 1 d . . . N3 N 1.0643(4) 0.63965(14) 0.58196(11) 0.0540(6) Uani 1 1 d . . . N4 N 1.0802(4) 0.57364(14) 0.63542(11) 0.0583(6) Uani 1 1 d . . . C1 C 0.8526(4) 0.42308(15) 0.63969(13) 0.0497(6) Uani 1 1 d . . . C2 C 1.0098(5) 0.37626(18) 0.69770(15) 0.0630(7) Uani 1 1 d . . . H2 H 1.1566 0.4003 0.7136 0.076 Uiso 1 1 calc R . . C3 C 0.9485(6) 0.2942(2) 0.73171(16) 0.0741(9) Uani 1 1 d . . . H3 H 1.0528 0.2641 0.7714 0.089 Uiso 1 1 calc R . . C4 C 0.7352(6) 0.25715(19) 0.70714(16) 0.0744(9) Uani 1 1 d . . . H4 H 0.6958 0.2007 0.7293 0.089 Uiso 1 1 calc R . . C5 C 0.5784(5) 0.30245(19) 0.65014(16) 0.0705(8) Uani 1 1 d . . . H5 H 0.4327 0.2772 0.6340 0.085 Uiso 1 1 calc R . . C6 C 0.6373(5) 0.38589(18) 0.61654(14) 0.0602(7) Uani 1 1 d . . . H6 H 0.5303 0.4169 0.5781 0.072 Uiso 1 1 calc R . . C7 C 0.9135(4) 0.51130(16) 0.60370(13) 0.0485(6) Uani 1 1 d . . . C8 C 1.2189(5) 0.72545(19) 0.59068(15) 0.0644(8) Uani 1 1 d . . . H8 H 1.2053 0.7661 0.6322 0.077 Uiso 1 1 calc R . . C9 C 1.4574(6) 0.6872(3) 0.6082(2) 0.0909(10) Uani 1 1 d . . . H9A H 1.4711 0.6440 0.5693 0.136 Uiso 1 1 calc R . . H9B H 1.4940 0.6504 0.6536 0.136 Uiso 1 1 calc R . . H9C H 1.5589 0.7427 0.6129 0.136 Uiso 1 1 calc R . . C10 C 1.1512(5) 0.78901(18) 0.52172(15) 0.0645(8) Uani 1 1 d . . . H10A H 1.2704 0.8368 0.5235 0.077 Uiso 1 1 calc R . . H10B H 1.1373 0.7461 0.4794 0.077 Uiso 1 1 calc R . . C11 C 0.9351(5) 0.84486(16) 0.51099(16) 0.0614(7) Uani 1 1 d . . . C12 C 0.8359(5) 0.89779(15) 0.44015(14) 0.0548(7) Uani 1 1 d . . . C13 C 0.9404(5) 0.9005(2) 0.38517(16) 0.0698(8) Uani 1 1 d . . . H13 H 1.0789 0.8692 0.3921 0.084 Uiso 1 1 calc R . . C14 C 0.8400(6) 0.9497(2) 0.31968(18) 0.0847(9) Uani 1 1 d . . . H14 H 0.9105 0.9504 0.2826 0.102 Uiso 1 1 calc R . . C15 C 0.6397(7) 0.9967(2) 0.3092(2) 0.0889(11) Uani 1 1 d . . . H15 H 0.5756 1.0307 0.2654 0.107 Uiso 1 1 calc R . . C16 C 0.5296(6) 0.9948(2) 0.3629(2) 0.0871(10) Uani 1 1 d . . . H16 H 0.3913 1.0265 0.3555 0.105 Uiso 1 1 calc R . . C17 C 0.6294(5) 0.94477(19) 0.42789(18) 0.0728(8) Uani 1 1 d . . . H17 H 0.5561 0.9426 0.4643 0.087 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 O1 0.122(2) 0.0715(12) 0.0870(15) 0.0047(10) 0.0629(15) 0.0076(12) N1 0.0541(13) 0.0526(11) 0.0603(13) 0.0033(9) 0.0086(10) -0.0053(10) N2 0.0534(13) 0.0556(12) 0.0626(14) 0.0054(9) 0.0112(11) -0.0038(10) N3 0.0545(13) 0.0516(11) 0.0524(13) 0.0020(9) 0.0101(10) -0.0081(9) N4 0.0625(14) 0.0527(11) 0.0558(12) 0.0031(9) 0.0109(10) -0.0109(10) C1 0.0535(14) 0.0418(11) 0.0510(14) -0.0054(10) 0.0108(11) -0.0041(10) C2 0.0605(17) 0.0578(14) 0.0658(17) 0.0014(12) 0.0103(13) -0.0031(12) C3 0.089(2) 0.0595(16) 0.0684(19) 0.0106(13) 0.0146(16) 0.0016(15) C4 0.103(3) 0.0513(14) 0.0735(19) 0.0000(13) 0.0322(18) -0.0140(16) C5 0.077(2) 0.0630(16) 0.0723(19) -0.0130(14) 0.0233(16) -0.0253(14) C6 0.0613(17) 0.0535(14) 0.0614(16) -0.0049(11) 0.0108(13) -0.0100(12) C7 0.0448(13) 0.0480(12) 0.0507(14) -0.0057(10) 0.0108(11) -0.0020(10) C8 0.0656(18) 0.0585(14) 0.0707(18) -0.0039(12) 0.0224(14) -0.0165(13) C9 0.0580(19) 0.099(2) 0.111(3) 0.024(2) 0.0180(18) -0.0090(17) C10 0.0678(18) 0.0578(14) 0.0710(18) 0.0067(12) 0.0249(14) -0.0140(14) C11 0.081(2) 0.0384(12) 0.0727(18) -0.0060(11) 0.0355(16) -0.0140(12) C12 0.0659(17) 0.0332(11) 0.0706(17) -0.0062(10) 0.0281(14) -0.0113(11) C13 0.0739(19) 0.0674(16) 0.074(2) 0.0096(14) 0.0312(16) 0.0013(14) C14 0.090(2) 0.088(2) 0.082(2) 0.0199(17) 0.0352(18) 0.0036(19) C15 0.096(3) 0.0675(18) 0.094(3) 0.0199(16) 0.013(2) 0.0034(18) C16 0.079(2) 0.0609(17) 0.116(3) 0.0059(17) 0.021(2) 0.0109(16) C17 0.084(2) 0.0523(14) 0.093(2) -0.0112(14) 0.0427(18) -0.0040(15) _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 C11 1.218(3) . ? N1 N2 1.309(3) . ? N1 C7 1.342(3) . ? N2 N3 1.310(3) . ? N3 N4 1.326(3) . ? N3 C8 1.473(3) . ? N4 C7 1.329(3) . ? C1 C6 1.373(3) . ? C1 C2 1.390(3) . ? C1 C7 1.465(3) . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C3 C4 1.362(4) . ? C3 H3 0.9300 . ? C4 C5 1.369(4) . ? C4 H4 0.9300 . ? C5 C6 1.385(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.509(4) . ? C8 C10 1.514(4) . ? C8 H8 0.9800 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.496(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.486(4) . ? C12 C13 1.379(4) . ? C12 C17 1.385(4) . ? C13 C14 1.384(4) . ? C13 H13 0.9300 . ? C14 C15 1.355(5) . ? C14 H14 0.9300 . ? C15 C16 1.380(5) . ? C15 H15 0.9300 . ? C16 C17 1.382(4) . ? C16 H16 0.9300 . ? C17 H17 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 C7 106.30(18) . . ? N1 N2 N3 106.22(19) . . ? N2 N3 N4 114.07(19) . . ? N2 N3 C8 123.9(2) . . ? N4 N3 C8 122.0(2) . . ? N3 N4 C7 101.21(19) . . ? C6 C1 C2 119.0(2) . . ? C6 C1 C7 120.0(2) . . ? C2 C1 C7 121.0(2) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 120.4(2) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? N4 C7 N1 112.2(2) . . ? N4 C7 C1 124.4(2) . . ? N1 C7 C1 123.4(2) . . ? N3 C8 C9 109.0(2) . . ? N3 C8 C10 109.3(2) . . ? C9 C8 C10 113.0(3) . . ? N3 C8 H8 108.5 . . ? C9 C8 H8 108.5 . . ? C10 C8 H8 108.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C8 114.3(2) . . ? C11 C10 H10A 108.7 . . ? C8 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C8 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? O1 C11 C12 120.4(3) . . ? O1 C11 C10 120.8(3) . . ? C12 C11 C10 118.8(3) . . ? C13 C12 C17 118.4(3) . . ? C13 C12 C11 122.3(3) . . ? C17 C12 C11 119.3(3) . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.8(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C17 118.5(3) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C16 C17 C12 121.6(3) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? 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 C7 N1 N2 N3 -0.4(3) . . . . ? N1 N2 N3 N4 0.3(3) . . . . ? N1 N2 N3 C8 179.7(2) . . . . ? N2 N3 N4 C7 -0.1(3) . . . . ? C8 N3 N4 C7 -179.5(2) . . . . ? C6 C1 C2 C3 -0.6(4) . . . . ? C7 C1 C2 C3 179.0(2) . . . . ? C1 C2 C3 C4 1.8(4) . . . . ? C2 C3 C4 C5 -1.9(5) . . . . ? C3 C4 C5 C6 0.7(5) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? C7 C1 C6 C5 179.9(2) . . . . ? C4 C5 C6 C1 0.5(4) . . . . ? N3 N4 C7 N1 -0.2(3) . . . . ? N3 N4 C7 C1 -179.2(2) . . . . ? N2 N1 C7 N4 0.4(3) . . . . ? N2 N1 C7 C1 179.3(2) . . . . ? C6 C1 C7 N4 154.9(2) . . . . ? C2 C1 C7 N4 -24.7(4) . . . . ? C6 C1 C7 N1 -23.9(4) . . . . ? C2 C1 C7 N1 156.5(2) . . . . ? N2 N3 C8 C9 -120.8(3) . . . . ? N4 N3 C8 C9 58.6(3) . . . . ? N2 N3 C8 C10 3.1(4) . . . . ? N4 N3 C8 C10 -177.5(2) . . . . ? N3 C8 C10 C11 70.2(3) . . . . ? C9 C8 C10 C11 -168.3(2) . . . . ? C8 C10 C11 O1 10.0(4) . . . . ? C8 C10 C11 C12 -171.3(2) . . . . ? O1 C11 C12 C13 176.1(3) . . . . ? C10 C11 C12 C13 -2.6(3) . . . . ? O1 C11 C12 C17 -5.1(4) . . . . ? C10 C11 C12 C17 176.2(2) . . . . ? C17 C12 C13 C14 0.3(4) . . . . ? C11 C12 C13 C14 179.1(2) . . . . ? C12 C13 C14 C15 0.9(5) . . . . ? C13 C14 C15 C16 -1.4(5) . . . . ? C14 C15 C16 C17 0.7(5) . . . . ? C15 C16 C17 C12 0.5(4) . . . . ? C13 C12 C17 C16 -1.0(4) . . . . ? C11 C12 C17 C16 -179.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.245 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.059 data_2 _database_code_depnum_ccdc_archive 'CCDC 836790' #TrackingRef '- 2ee.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N3 O' _chemical_formula_weight 265.31 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 0.0016 '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 ' 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 9.912(4) _cell_length_b 13.636(5) _cell_length_c 10.633(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.257(5) _cell_angle_gamma 90.00 _cell_volume 1393.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9799 _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_type 'Bruker APEX II area detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8954 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.09 _reflns_number_total 2442 _reflns_number_gt 1725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEX II' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0670P)^2^+0.2060P] 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_number_reflns 2442 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.37006(17) 0.51009(13) 0.28400(18) 0.0553(5) Uani 1 1 d . . . C2 C 0.30482(17) 0.49724(13) 0.15387(18) 0.0540(5) Uani 1 1 d . . . C3 C 0.2388(2) 0.57478(15) 0.0773(2) 0.0702(6) Uani 1 1 d . . . H3 H 0.1924 0.5659 -0.0093 0.084 Uiso 1 1 calc R . . C4 C 0.2456(2) 0.66362(16) 0.1354(2) 0.0800(7) Uani 1 1 d . . . H4 H 0.2038 0.7171 0.0869 0.096 Uiso 1 1 calc R . . C5 C 0.3134(2) 0.67769(16) 0.2661(2) 0.0750(6) Uani 1 1 d . . . H5 H 0.3163 0.7402 0.3018 0.090 Uiso 1 1 calc R . . C6 C 0.37506(19) 0.60183(15) 0.3423(2) 0.0654(5) Uani 1 1 d . . . H6 H 0.4187 0.6110 0.4295 0.078 Uiso 1 1 calc R . . C7 C 0.2845(2) 0.34843(14) 0.0065(2) 0.0686(6) Uani 1 1 d . . . H7 H 0.1970 0.3752 -0.0462 0.082 Uiso 1 1 calc R . . C8 C 0.3981(3) 0.36617(18) -0.0644(2) 0.0907(7) Uani 1 1 d . . . H8A H 0.4051 0.4351 -0.0798 0.136 Uiso 1 1 calc R . . H8B H 0.3756 0.3319 -0.1458 0.136 Uiso 1 1 calc R . . H8C H 0.4854 0.3426 -0.0124 0.136 Uiso 1 1 calc R . . C9 C 0.2647(2) 0.24065(15) 0.0268(2) 0.0725(6) Uani 1 1 d . . . H9A H 0.2497 0.2079 -0.0565 0.087 Uiso 1 1 calc R . . H9B H 0.3503 0.2149 0.0819 0.087 Uiso 1 1 calc R . . C10 C 0.14669(19) 0.21422(15) 0.0864(2) 0.0674(6) Uani 1 1 d . . . C11 C 0.13396(17) 0.11083(14) 0.12607(18) 0.0611(5) Uani 1 1 d . . . C12 C 0.0290(2) 0.08470(18) 0.1851(2) 0.0797(7) Uani 1 1 d . . . H12 H -0.0331 0.1322 0.1990 0.096 Uiso 1 1 calc R . . C13 C 0.0155(2) -0.0102(2) 0.2234(3) 0.0871(7) Uani 1 1 d . . . H13 H -0.0556 -0.0264 0.2628 0.105 Uiso 1 1 calc R . . C14 C 0.1052(2) -0.08071(17) 0.2040(2) 0.0786(6) Uani 1 1 d . . . H14 H 0.0953 -0.1450 0.2296 0.094 Uiso 1 1 calc R . . C15 C 0.2100(2) -0.05670(16) 0.1469(3) 0.0816(7) Uani 1 1 d . . . H15 H 0.2724 -0.1047 0.1349 0.098 Uiso 1 1 calc R . . C16 C 0.2241(2) 0.03777(15) 0.1070(2) 0.0724(6) Uani 1 1 d . . . H16 H 0.2949 0.0529 0.0669 0.087 Uiso 1 1 calc R . . N1 N 0.42147(18) 0.42134(13) 0.33413(17) 0.0730(5) Uani 1 1 d . . . N2 N 0.39175(19) 0.35647(12) 0.24084(17) 0.0742(5) Uani 1 1 d . . . N3 N 0.32009(15) 0.40072(11) 0.13136(15) 0.0610(4) Uani 1 1 d . . . O1 O 0.06373(16) 0.27603(12) 0.1008(2) 0.1012(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0520(10) 0.0630(12) 0.0498(11) 0.0054(9) 0.0105(8) -0.0046(8) C2 0.0530(10) 0.0598(11) 0.0475(11) 0.0047(8) 0.0092(8) -0.0008(8) C3 0.0781(13) 0.0707(13) 0.0541(12) 0.0085(10) 0.0017(10) 0.0047(10) C4 0.0894(15) 0.0642(13) 0.0789(16) 0.0107(12) 0.0066(12) 0.0122(11) C5 0.0741(13) 0.0676(13) 0.0803(16) -0.0070(12) 0.0131(11) -0.0039(10) C6 0.0581(11) 0.0796(14) 0.0569(12) -0.0051(11) 0.0111(9) -0.0083(10) C7 0.0789(13) 0.0708(13) 0.0508(12) -0.0027(10) 0.0061(10) 0.0049(10) C8 0.125(2) 0.0881(16) 0.0644(15) -0.0031(12) 0.0346(14) -0.0096(14) C9 0.0780(13) 0.0682(13) 0.0717(14) -0.0067(11) 0.0191(11) 0.0041(10) C10 0.0568(11) 0.0745(13) 0.0661(13) -0.0124(10) 0.0060(10) 0.0085(10) C11 0.0500(10) 0.0726(13) 0.0558(12) -0.0103(9) 0.0040(8) -0.0001(9) C12 0.0533(11) 0.0973(17) 0.0887(17) -0.0046(13) 0.0180(11) 0.0068(11) C13 0.0627(13) 0.1070(19) 0.0931(19) 0.0059(14) 0.0219(12) -0.0109(13) C14 0.0751(14) 0.0812(15) 0.0767(16) -0.0013(12) 0.0134(12) -0.0094(11) C15 0.0895(15) 0.0669(14) 0.0948(18) -0.0056(12) 0.0347(13) 0.0027(11) C16 0.0761(13) 0.0695(13) 0.0775(15) -0.0095(11) 0.0302(11) -0.0003(10) N1 0.0844(11) 0.0746(12) 0.0516(10) 0.0081(9) 0.0011(9) 0.0009(9) N2 0.0878(12) 0.0688(11) 0.0582(12) 0.0111(9) 0.0031(9) 0.0088(9) N3 0.0684(10) 0.0642(10) 0.0457(9) 0.0060(7) 0.0049(7) 0.0040(7) O1 0.0785(10) 0.0851(11) 0.1442(17) -0.0044(10) 0.0353(10) 0.0199(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 C1 N1 1.369(2) . ? C1 C2 1.387(3) . ? C1 C6 1.392(3) . ? C2 N3 1.353(2) . ? C2 C3 1.395(3) . ? C3 C4 1.354(3) . ? C3 H3 0.9300 . ? C4 C5 1.400(3) . ? C4 H4 0.9300 . ? C5 C6 1.362(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N3 1.471(3) . ? C7 C9 1.505(3) . ? C7 C8 1.521(3) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.505(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O1 1.213(2) . ? C10 C11 1.486(3) . ? C11 C16 1.386(3) . ? C11 C12 1.387(3) . ? C12 C13 1.373(3) . ? C12 H12 0.9300 . ? C13 C14 1.359(3) . ? C13 H13 0.9300 . ? C14 C15 1.366(3) . ? C14 H14 0.9300 . ? C15 C16 1.374(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N1 N2 1.307(2) . ? N2 N3 1.348(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 N1 C1 C2 108.31(17) . . ? N1 C1 C6 130.71(18) . . ? C2 C1 C6 120.97(17) . . ? N3 C2 C1 104.74(15) . . ? N3 C2 C3 133.69(18) . . ? C1 C2 C3 121.54(18) . . ? C4 C3 C2 116.6(2) . . ? C4 C3 H3 121.7 . . ? C2 C3 H3 121.7 . . ? C3 C4 C5 122.2(2) . . ? C3 C4 H4 118.9 . . ? C5 C4 H4 118.9 . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 117.2(2) . . ? C5 C6 H6 121.4 . . ? C1 C6 H6 121.4 . . ? N3 C7 C9 110.77(17) . . ? N3 C7 C8 109.16(17) . . ? C9 C7 C8 111.41(18) . . ? N3 C7 H7 108.5 . . ? C9 C7 H7 108.5 . . ? C8 C7 H7 108.5 . . ? 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 . . ? C10 C9 C7 115.89(17) . . ? C10 C9 H9A 108.3 . . ? C7 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C7 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? O1 C10 C11 121.0(2) . . ? O1 C10 C9 120.5(2) . . ? C11 C10 C9 118.43(17) . . ? C16 C11 C12 117.6(2) . . ? C16 C11 C10 122.51(19) . . ? C12 C11 C10 119.86(18) . . ? C13 C12 C11 121.0(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.7(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 120.7(2) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? N2 N1 C1 108.05(16) . . ? N1 N2 N3 108.95(16) . . ? N2 N3 C2 109.93(15) . . ? N2 N3 C7 121.37(16) . . ? C2 N3 C7 128.22(15) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.119 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.031