# Electronic Supplementary Material (ESI) for Organic and 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_email jianghf@scut.edu.cn _publ_contact_author_name 'Jiang, Huanfeng' loop_ _publ_author_name 'Huanfeng Jiang' 'Xiaochen Ji' 'Yibiao Li' 'Zhengwang Chen' 'Azhong Wang' data_1 _database_code_depnum_ccdc_archive 'CCDC 801571' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H19 N O4' _chemical_formula_sum 'C21 H19 N O4' _chemical_formula_weight 349.37 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 c ' _symmetry_space_group_name_Hall 'C -2yc ' 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 19.404(4) _cell_length_b 8.0536(16) _cell_length_c 11.589(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.32(3) _cell_angle_gamma 90.00 _cell_volume 1769.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2895 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.89 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6916 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0566 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3102 _reflns_number_gt 1742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _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^)+(0.0443P)^2^+0.5456P] 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 0.9(18) _refine_ls_number_reflns 3102 _refine_ls_number_parameters 237 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1056 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _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 0.7038(2) 0.2194(5) 0.7941(4) 0.0490(10) Uani 1 1 d . . . C2 C 0.73468(18) 0.2662(5) 0.6938(3) 0.0430(9) Uani 1 1 d . . . C3 C 0.69469(19) 0.2800(5) 0.5859(3) 0.0490(10) Uani 1 1 d . . . H3 H 0.6471 0.2537 0.5746 0.059 Uiso 1 1 calc R . . N1 N 0.72079(16) 0.3323(4) 0.4886(3) 0.0500(9) Uani 1 1 d . . . C5 C 0.79054(19) 0.3806(5) 0.5088(4) 0.0488(10) Uani 1 1 d . . . H5 H 0.8076 0.4245 0.4460 0.059 Uiso 1 1 calc R . . C6 C 0.83484(18) 0.3677(5) 0.6136(3) 0.0423(9) Uani 1 1 d . . . C7 C 0.6769(2) 0.3374(5) 0.3733(4) 0.0501(10) Uani 1 1 d . . . C8 C 0.6081(2) 0.3918(5) 0.3556(4) 0.0569(11) Uani 1 1 d . . . H8 H 0.5894 0.4258 0.4193 0.068 Uiso 1 1 calc R . . C9 C 0.5671(2) 0.3953(6) 0.2423(4) 0.0647(13) Uani 1 1 d . . . H9 H 0.5204 0.4304 0.2299 0.078 Uiso 1 1 calc R . . C10 C 0.5947(3) 0.3475(6) 0.1486(4) 0.0692(13) Uani 1 1 d . . . H10 H 0.5668 0.3507 0.0726 0.083 Uiso 1 1 calc R . . C11 C 0.6631(2) 0.2951(7) 0.1659(4) 0.0701(14) Uani 1 1 d . . . H11 H 0.6817 0.2636 0.1017 0.084 Uiso 1 1 calc R . . C12 C 0.7045(2) 0.2885(6) 0.2781(4) 0.0578(11) Uani 1 1 d . . . H12 H 0.7509 0.2514 0.2898 0.069 Uiso 1 1 calc R . . C13 C 0.84960(19) 0.1190(5) 0.7506(4) 0.0450(9) Uani 1 1 d . . . C14 C 0.8852(2) 0.0823(6) 0.8631(4) 0.0570(11) Uani 1 1 d . . . H14 H 0.8902 0.1638 0.9212 0.068 Uiso 1 1 calc R . . C15 C 0.9139(2) -0.0740(7) 0.8921(5) 0.0711(14) Uani 1 1 d . . . H15 H 0.9372 -0.0973 0.9692 0.085 Uiso 1 1 calc R . . C16 C 0.9076(2) -0.1932(6) 0.8067(5) 0.0725(14) Uani 1 1 d . . . H16 H 0.9276 -0.2973 0.8253 0.087 Uiso 1 1 calc R . . C17 C 0.8716(3) -0.1600(6) 0.6927(5) 0.0666(12) Uani 1 1 d . . . H17 H 0.8667 -0.2420 0.6350 0.080 Uiso 1 1 calc R . . C18 C 0.8430(2) -0.0043(5) 0.6650(4) 0.0541(11) Uani 1 1 d . . . H18 H 0.8191 0.0184 0.5881 0.065 Uiso 1 1 calc R . . C19 C 0.9074(2) 0.4287(5) 0.6303(4) 0.0461(9) Uani 1 1 d . . . C20 C 0.9927(2) 0.5630(6) 0.5429(4) 0.0672(13) Uani 1 1 d . . . H20A H 0.9986 0.6543 0.5974 0.101 Uiso 1 1 calc R . . H20B H 0.9990 0.6013 0.4673 0.101 Uiso 1 1 calc R . . H20C H 1.0271 0.4789 0.5720 0.101 Uiso 1 1 calc R . . C21 C 0.6041(2) 0.1104(7) 0.8547(4) 0.0751(14) Uani 1 1 d . . . H21A H 0.6362 0.0446 0.9110 0.113 Uiso 1 1 calc R . . H21B H 0.5627 0.0463 0.8228 0.113 Uiso 1 1 calc R . . H21C H 0.5910 0.2075 0.8931 0.113 Uiso 1 1 calc R . . C4 C 0.81451(19) 0.2879(5) 0.7201(3) 0.0431(9) Uani 1 1 d . . . H4 H 0.8283 0.3620 0.7882 0.052 Uiso 1 1 calc R . . O1 O 0.73331(14) 0.2324(4) 0.8965(3) 0.0668(9) Uani 1 1 d . . . O2 O 0.63793(14) 0.1601(4) 0.7600(2) 0.0621(8) Uani 1 1 d . . . O3 O 0.94950(14) 0.4254(4) 0.7237(3) 0.0594(8) Uani 1 1 d . . . O4 O 0.92255(14) 0.4943(4) 0.5308(2) 0.0556(7) 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 0.045(2) 0.059(2) 0.046(3) -0.002(2) 0.015(2) -0.001(2) C2 0.040(2) 0.048(2) 0.041(2) -0.0026(18) 0.0072(18) -0.0006(18) C3 0.045(2) 0.058(3) 0.046(3) 0.001(2) 0.013(2) -0.0011(19) N1 0.0434(19) 0.067(2) 0.038(2) 0.0040(18) 0.0056(16) -0.0060(17) C5 0.043(2) 0.052(3) 0.051(3) 0.003(2) 0.010(2) -0.0064(18) C6 0.043(2) 0.045(2) 0.039(2) 0.0002(18) 0.0078(18) -0.0036(17) C7 0.049(2) 0.057(3) 0.042(3) 0.003(2) 0.004(2) -0.005(2) C8 0.054(3) 0.069(3) 0.045(3) -0.003(2) 0.004(2) 0.002(2) C9 0.055(3) 0.072(3) 0.060(3) 0.001(3) -0.003(2) -0.001(2) C10 0.071(3) 0.083(3) 0.047(3) 0.002(3) -0.004(2) -0.010(3) C11 0.067(3) 0.095(4) 0.048(3) -0.007(3) 0.012(2) -0.010(3) C12 0.049(2) 0.077(3) 0.045(3) 0.000(2) 0.005(2) -0.003(2) C13 0.0404(19) 0.053(2) 0.042(2) 0.0036(19) 0.0090(17) 0.0017(18) C14 0.052(2) 0.064(3) 0.051(3) 0.001(2) 0.004(2) 0.005(2) C15 0.064(3) 0.085(4) 0.063(3) 0.018(3) 0.011(2) 0.022(3) C16 0.073(3) 0.064(3) 0.088(4) 0.024(3) 0.032(3) 0.024(3) C17 0.083(3) 0.048(3) 0.074(3) 0.011(2) 0.029(3) 0.014(2) C18 0.067(3) 0.054(3) 0.042(2) -0.002(2) 0.013(2) 0.006(2) C19 0.050(2) 0.043(2) 0.046(2) -0.003(2) 0.014(2) -0.0003(19) C20 0.049(3) 0.076(3) 0.080(4) 0.002(3) 0.021(2) -0.014(2) C21 0.071(3) 0.102(4) 0.060(3) 0.004(3) 0.030(3) -0.020(3) C4 0.049(2) 0.045(2) 0.036(2) -0.0011(19) 0.0094(17) -0.0010(19) O1 0.0542(17) 0.101(3) 0.0441(19) -0.0026(17) 0.0085(14) -0.0103(16) O2 0.0519(16) 0.090(2) 0.0459(17) 0.0001(16) 0.0138(13) -0.0178(16) O3 0.0511(17) 0.073(2) 0.0505(19) 0.0033(16) 0.0022(15) -0.0096(14) O4 0.0505(15) 0.0687(18) 0.0488(17) -0.0011(15) 0.0131(13) -0.0132(14) _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 O1 1.207(5) . ? C1 O2 1.343(5) . ? C1 C2 1.466(5) . ? C2 C3 1.328(5) . ? C2 C4 1.524(5) . ? C3 N1 1.396(5) . ? C3 H3 0.9300 . ? N1 C5 1.379(5) . ? N1 C7 1.424(5) . ? C5 C6 1.334(5) . ? C5 H5 0.9300 . ? C6 C19 1.465(5) . ? C6 C4 1.516(5) . ? C7 C8 1.379(6) . ? C7 C12 1.382(5) . ? C8 C9 1.383(6) . ? C8 H8 0.9300 . ? C9 C10 1.365(6) . ? C9 H9 0.9300 . ? C10 C11 1.366(7) . ? C10 H10 0.9300 . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.371(5) . ? C13 C18 1.391(5) . ? C13 C4 1.528(5) . ? C14 C15 1.388(6) . ? C14 H14 0.9300 . ? C15 C16 1.366(7) . ? C15 H15 0.9300 . ? C16 C17 1.382(7) . ? C16 H16 0.9300 . ? C17 C18 1.381(6) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 O3 1.210(5) . ? C19 O4 1.356(5) . ? C20 O4 1.448(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O2 1.451(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C4 H4 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 122.9(4) . . ? O1 C1 C2 124.7(4) . . ? O2 C1 C2 112.5(4) . . ? C3 C2 C1 120.8(3) . . ? C3 C2 C4 122.9(3) . . ? C1 C2 C4 116.2(3) . . ? C2 C3 N1 123.1(3) . . ? C2 C3 H3 118.4 . . ? N1 C3 H3 118.4 . . ? C5 N1 C3 117.4(3) . . ? C5 N1 C7 121.3(3) . . ? C3 N1 C7 121.3(3) . . ? C6 C5 N1 123.4(4) . . ? C6 C5 H5 118.3 . . ? N1 C5 H5 118.3 . . ? C5 C6 C19 120.5(3) . . ? C5 C6 C4 123.0(3) . . ? C19 C6 C4 116.4(3) . . ? C8 C7 C12 120.0(4) . . ? C8 C7 N1 121.0(4) . . ? C12 C7 N1 119.0(3) . . ? C7 C8 C9 119.3(4) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.4(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 120.3(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 119.7(4) . . ? C11 C12 H12 120.2 . . ? C7 C12 H12 120.2 . . ? C14 C13 C18 118.4(4) . . ? C14 C13 C4 121.4(4) . . ? C18 C13 C4 120.1(4) . . ? C13 C14 C15 121.4(4) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C16 C15 C14 119.5(5) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.4(5) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 119.6(5) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C13 120.8(4) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? O3 C19 O4 122.9(4) . . ? O3 C19 C6 123.8(4) . . ? O4 C19 C6 113.3(3) . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C6 C4 C2 108.4(3) . . ? C6 C4 C13 112.7(3) . . ? C2 C4 C13 109.1(3) . . ? C6 C4 H4 108.8 . . ? C2 C4 H4 108.8 . . ? C13 C4 H4 108.8 . . ? C1 O2 C21 115.5(3) . . ? C19 O4 C20 115.9(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.222 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.052 # Attachment '4q.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 801572' #TrackingRef '4q.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 N3' _chemical_formula_sum 'C19 H13 N3' _chemical_formula_weight 283.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 13.657(3) _cell_length_b 8.1149(16) _cell_length_c 13.751(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.69(3) _cell_angle_gamma 90.00 _cell_volume 1518.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2895 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.89 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9938 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2728 _reflns_number_gt 1848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _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^)+(0.0576P)^2^+0.1912P] 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 2728 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.24493(12) 0.0335(2) 0.72009(11) 0.0618(4) Uani 1 1 d . . . C2 C 0.29859(12) -0.0037(2) 0.80702(12) 0.0647(4) Uani 1 1 d . . . H2 H 0.2667 -0.0350 0.8613 0.078 Uiso 1 1 calc R . . C3 C 0.39921(13) 0.0060(2) 0.81246(12) 0.0703(5) Uani 1 1 d . . . H3 H 0.4354 -0.0175 0.8711 0.084 Uiso 1 1 calc R . . C4 C 0.44707(14) 0.0499(2) 0.73227(13) 0.0741(5) Uani 1 1 d . . . H4 H 0.5153 0.0550 0.7363 0.089 Uiso 1 1 calc R . . C5 C 0.39331(14) 0.0863(3) 0.64619(13) 0.0812(5) Uani 1 1 d . . . H5 H 0.4255 0.1159 0.5918 0.097 Uiso 1 1 calc R . . C6 C 0.29235(14) 0.0793(2) 0.63965(12) 0.0769(5) Uani 1 1 d . . . H6 H 0.2564 0.1054 0.5813 0.092 Uiso 1 1 calc R . . N1 N 0.13993(10) 0.02448(18) 0.71470(10) 0.0680(4) Uani 1 1 d . . . C7 C 0.08783(13) -0.0660(2) 0.64304(11) 0.0653(4) Uani 1 1 d . . . H7 H 0.1216 -0.1118 0.5936 0.078 Uiso 1 1 calc R . . C8 C -0.00864(12) -0.09083(19) 0.64149(11) 0.0609(4) Uani 1 1 d . . . C10 C -0.00821(13) 0.0707(2) 0.79147(11) 0.0651(4) Uani 1 1 d . . . C11 C 0.08850(13) 0.0889(2) 0.78800(12) 0.0685(5) Uani 1 1 d . . . H11 H 0.1230 0.1480 0.8376 0.082 Uiso 1 1 calc R . . C12 C -0.05553(13) -0.1946(2) 0.56776(12) 0.0702(5) Uani 1 1 d . . . C13 C -0.05317(14) 0.1419(3) 0.87142(13) 0.0803(5) Uani 1 1 d . . . C14 C -0.15448(11) 0.0861(2) 0.66542(11) 0.0603(4) Uani 1 1 d . . . C15 C -0.13454(14) 0.2414(2) 0.63207(13) 0.0778(5) Uani 1 1 d . . . H15 H -0.0713 0.2837 0.6424 0.093 Uiso 1 1 calc R . . C16 C -0.20774(19) 0.3357(3) 0.58324(15) 0.0972(7) Uani 1 1 d . . . H16 H -0.1938 0.4411 0.5617 0.117 Uiso 1 1 calc R . . C17 C -0.30081(18) 0.2726(4) 0.56692(16) 0.1023(8) Uani 1 1 d . . . H17 H -0.3502 0.3355 0.5345 0.123 Uiso 1 1 calc R . . C18 C -0.32076(16) 0.1184(4) 0.59811(17) 0.1040(8) Uani 1 1 d . . . H18 H -0.3836 0.0751 0.5856 0.125 Uiso 1 1 calc R . . C19 C -0.24881(14) 0.0258(3) 0.64805(14) 0.0845(6) Uani 1 1 d . . . H19 H -0.2639 -0.0786 0.6704 0.101 Uiso 1 1 calc R . . C9 C -0.07407(12) -0.0210(2) 0.71515(11) 0.0622(4) Uani 1 1 d . . . H9 H -0.1050 -0.1130 0.7472 0.075 Uiso 1 1 calc R . . N2 N -0.09657(13) -0.2785(2) 0.51187(12) 0.0937(5) Uani 1 1 d . . . N3 N -0.09056(15) 0.1961(3) 0.93547(14) 0.1182(7) 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 0.0687(10) 0.0595(9) 0.0561(9) -0.0050(7) -0.0009(8) 0.0066(7) C2 0.0767(11) 0.0629(10) 0.0541(9) 0.0067(7) 0.0035(8) -0.0027(8) C3 0.0766(11) 0.0730(11) 0.0595(10) 0.0107(8) -0.0048(8) -0.0001(9) C4 0.0733(11) 0.0755(12) 0.0733(11) 0.0101(9) 0.0046(9) 0.0018(9) C5 0.0838(13) 0.0966(14) 0.0646(11) 0.0171(9) 0.0141(9) 0.0078(10) C6 0.0852(12) 0.0949(14) 0.0500(9) 0.0095(8) 0.0015(8) 0.0170(10) N1 0.0707(9) 0.0773(9) 0.0549(7) -0.0183(7) -0.0006(6) 0.0059(7) C7 0.0797(11) 0.0649(10) 0.0504(9) -0.0126(7) 0.0004(8) 0.0098(8) C8 0.0770(11) 0.0560(9) 0.0487(8) -0.0100(7) -0.0010(7) 0.0055(8) C10 0.0792(11) 0.0665(10) 0.0492(8) -0.0116(7) 0.0023(8) 0.0085(8) C11 0.0778(11) 0.0734(11) 0.0530(9) -0.0172(8) -0.0031(8) 0.0090(9) C12 0.0831(11) 0.0684(11) 0.0583(9) -0.0129(8) 0.0003(8) 0.0066(9) C13 0.0849(12) 0.0938(14) 0.0612(10) -0.0234(10) 0.0006(9) 0.0114(10) C14 0.0637(9) 0.0678(10) 0.0503(8) -0.0106(7) 0.0093(7) -0.0030(8) C15 0.0812(11) 0.0725(12) 0.0778(12) 0.0001(9) -0.0044(9) -0.0039(9) C16 0.1242(18) 0.0836(14) 0.0812(13) 0.0007(11) -0.0081(13) 0.0181(13) C17 0.0943(16) 0.138(2) 0.0719(13) -0.0210(14) -0.0082(12) 0.0411(16) C18 0.0648(12) 0.156(2) 0.0913(15) -0.0162(16) 0.0051(11) 0.0051(14) C19 0.0701(11) 0.1065(15) 0.0782(12) -0.0072(11) 0.0149(10) -0.0108(11) C9 0.0766(10) 0.0585(9) 0.0519(9) -0.0040(7) 0.0074(8) -0.0030(8) N2 0.1053(12) 0.0937(12) 0.0798(11) -0.0323(9) -0.0062(9) -0.0009(10) N3 0.1218(15) 0.1511(19) 0.0827(12) -0.0478(12) 0.0151(11) 0.0232(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.378(2) . ? C1 C2 1.383(2) . ? C1 N1 1.432(2) . ? C2 C3 1.372(2) . ? C2 H2 0.9300 . ? C3 C4 1.374(3) . ? C3 H3 0.9300 . ? C4 C5 1.373(2) . ? C4 H4 0.9300 . ? C5 C6 1.376(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N1 C11 1.378(2) . ? N1 C7 1.379(2) . ? C7 C8 1.331(2) . ? C7 H7 0.9300 . ? C8 C12 1.428(2) . ? C8 C9 1.514(2) . ? C10 C11 1.334(2) . ? C10 C13 1.424(2) . ? C10 C9 1.520(2) . ? C11 H11 0.9300 . ? C12 N2 1.139(2) . ? C13 N3 1.142(2) . ? C14 C15 1.376(2) . ? C14 C19 1.380(2) . ? C14 C9 1.519(2) . ? C15 C16 1.388(3) . ? C15 H15 0.9300 . ? C16 C17 1.372(3) . ? C16 H16 0.9300 . ? C17 C18 1.358(4) . ? C17 H17 0.9300 . ? C18 C19 1.375(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C9 H9 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.13(16) . . ? C6 C1 N1 120.45(15) . . ? C2 C1 N1 119.42(15) . . ? C3 C2 C1 119.47(16) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C4 C3 C2 120.73(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.45(17) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.67(17) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C1 C6 C5 119.54(16) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C11 N1 C7 117.42(14) . . ? C11 N1 C1 120.74(13) . . ? C7 N1 C1 121.35(13) . . ? C8 C7 N1 122.97(15) . . ? C8 C7 H7 118.5 . . ? N1 C7 H7 118.5 . . ? C7 C8 C12 119.09(15) . . ? C7 C8 C9 124.75(14) . . ? C12 C8 C9 116.12(15) . . ? C11 C10 C13 118.26(15) . . ? C11 C10 C9 124.14(15) . . ? C13 C10 C9 117.60(15) . . ? C10 C11 N1 123.37(15) . . ? C10 C11 H11 118.3 . . ? N1 C11 H11 118.3 . . ? N2 C12 C8 176.6(2) . . ? N3 C13 C10 178.5(2) . . ? C15 C14 C19 118.31(17) . . ? C15 C14 C9 121.24(15) . . ? C19 C14 C9 120.37(16) . . ? C14 C15 C16 120.79(19) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C17 C16 C15 119.6(2) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C18 C17 C16 120.0(2) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.5(2) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 120.8(2) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C8 C9 C14 110.95(12) . . ? C8 C9 C10 107.27(13) . . ? C14 C9 C10 113.32(13) . . ? C8 C9 H9 108.4 . . ? C14 C9 H9 108.4 . . ? C10 C9 H9 108.4 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.246 _refine_diff_density_min -0.114 _refine_diff_density_rms 0.038