# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email xdjiang@henu.edu.cn _publ_contact_author_name 'Xin-Dong Jiang' _publ_author_name 'Xin-Dong Jiang' data_jxd9-1 _database_code_depnum_ccdc_archive 'CCDC 878978' #TrackingRef 'web_deposit_cif_file_0_Xin-DongJiang_1337646570.jxd9-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 N O' _chemical_formula_weight 299.36 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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.65810(10) _cell_length_b 8.0433(2) _cell_length_c 50.1404(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3088.47(10) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9767 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14356 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -59 _diffrn_reflns_limit_l_max 59 _diffrn_reflns_theta_min 0.81 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2728 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+6.6369P] 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 2728 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0937 _refine_ls_wR_factor_ref 0.2160 _refine_ls_wR_factor_gt 0.2036 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 0.5954(5) -0.4781(5) 0.13285(9) 0.0545(11) Uani 1 1 d . . . H1 H 0.6321 -0.5883 0.1333 0.065 Uiso 1 1 calc R . . N1 N 0.5951(5) -0.3805(4) 0.11083(7) 0.0560(9) Uani 1 1 d . . . H2 H 0.6296 -0.4101 0.0952 0.067 Uiso 1 1 calc R . . C2 C 0.5306(5) -0.2259(5) 0.11753(8) 0.0484(10) Uani 1 1 d . . . C3 C 0.4911(5) -0.2293(5) 0.14434(8) 0.0479(10) Uani 1 1 d . . . C4 C 0.5337(5) -0.3906(5) 0.15439(8) 0.0499(10) Uani 1 1 d . . . C5 C 0.5138(6) -0.4583(5) 0.18148(9) 0.0541(11) Uani 1 1 d . . . C6 C 0.3942(6) -0.3952(6) 0.19972(9) 0.0603(12) Uani 1 1 d . . . H3 H 0.3258 -0.3042 0.1951 0.072 Uiso 1 1 calc R . . C7 C 0.3758(7) -0.4667(7) 0.22476(10) 0.0744(14) Uani 1 1 d . . . H4 H 0.2949 -0.4232 0.2367 0.089 Uiso 1 1 calc R . . C8 C 0.4768(8) -0.6023(7) 0.23216(11) 0.0839(17) Uani 1 1 d . . . H5 H 0.4650 -0.6496 0.2490 0.101 Uiso 1 1 calc R . . C9 C 0.5948(8) -0.6655(7) 0.21414(11) 0.0828(16) Uani 1 1 d . . . H6 H 0.6621 -0.7573 0.2188 0.099 Uiso 1 1 calc R . . C10 C 0.6146(7) -0.5954(6) 0.18940(10) 0.0687(13) Uani 1 1 d . . . H7 H 0.6964 -0.6395 0.1777 0.082 Uiso 1 1 calc R . . C11 C 0.4189(6) -0.0769(5) 0.15801(8) 0.0520(11) Uani 1 1 d . . . H8 H 0.2951 -0.0922 0.1613 0.062 Uiso 1 1 calc R . . H9 H 0.4763 -0.0625 0.1751 0.062 Uiso 1 1 calc R . . C12 C 0.4458(6) 0.0760(5) 0.14134(9) 0.0612(12) Uani 1 1 d . . . H10 H 0.3716 0.1640 0.1482 0.073 Uiso 1 1 calc R . . H11 H 0.5660 0.1121 0.1432 0.073 Uiso 1 1 calc R . . C13 C 0.4072(6) 0.0519(5) 0.11246(9) 0.0597(12) Uani 1 1 d . . . H12 H 0.2836 0.0212 0.1111 0.072 Uiso 1 1 calc R . . C14 C 0.5109(5) -0.0865(5) 0.09983(8) 0.0488(10) Uani 1 1 d . . . C15 C 0.5697(6) -0.0730(6) 0.07463(8) 0.0589(12) Uani 1 1 d . . . H13 H 0.6325 -0.1598 0.0670 0.071 Uiso 1 1 calc R . . C16 C 0.5355(7) 0.0759(6) 0.05938(9) 0.0626(12) Uani 1 1 d . . . C17 C 0.5765(9) 0.0934(7) 0.03241(10) 0.095(2) Uani 1 1 d . . . H14 H 0.6317 0.0063 0.0236 0.113 Uiso 1 1 calc R . . C18 C 0.5370(11) 0.2380(8) 0.01841(11) 0.115(3) Uani 1 1 d . . . H15 H 0.5643 0.2472 0.0004 0.138 Uiso 1 1 calc R . . C19 C 0.4571(9) 0.3669(8) 0.03154(11) 0.096(2) Uani 1 1 d . . . H16 H 0.4288 0.4633 0.0223 0.115 Uiso 1 1 calc R . . C20 C 0.4181(7) 0.3553(6) 0.05831(10) 0.0735(14) Uani 1 1 d . . . H17 H 0.3662 0.4444 0.0671 0.088 Uiso 1 1 calc R . . C21 C 0.4561(6) 0.2108(6) 0.07212(9) 0.0595(12) Uani 1 1 d . . . O1 O 0.4279(5) 0.2082(4) 0.09899(6) 0.0713(10) 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 0.048(2) 0.041(2) 0.075(3) -0.008(2) 0.004(2) 0.0018(19) N1 0.054(2) 0.050(2) 0.064(2) -0.0185(18) 0.0063(18) 0.0057(18) C2 0.041(2) 0.045(2) 0.059(3) -0.0150(19) -0.0006(19) -0.0017(18) C3 0.039(2) 0.048(2) 0.057(2) -0.0131(19) -0.0003(18) -0.0024(19) C4 0.041(2) 0.046(2) 0.063(3) -0.009(2) 0.0004(19) -0.0036(19) C5 0.053(3) 0.046(2) 0.064(3) -0.008(2) -0.008(2) -0.008(2) C6 0.065(3) 0.053(3) 0.062(3) -0.007(2) -0.004(2) 0.000(2) C7 0.082(4) 0.076(4) 0.066(3) -0.011(3) 0.000(3) -0.003(3) C8 0.105(5) 0.080(4) 0.066(3) 0.007(3) -0.009(3) -0.011(4) C9 0.088(4) 0.077(4) 0.084(4) 0.012(3) -0.008(3) 0.008(3) C10 0.065(3) 0.066(3) 0.075(3) 0.001(3) -0.005(3) 0.007(3) C11 0.056(3) 0.045(2) 0.055(2) -0.0122(19) 0.005(2) 0.003(2) C12 0.066(3) 0.054(3) 0.064(3) -0.013(2) 0.008(2) 0.007(2) C13 0.068(3) 0.052(3) 0.059(3) -0.007(2) 0.001(2) 0.004(2) C14 0.043(2) 0.048(2) 0.056(2) -0.0131(19) -0.0005(19) -0.0044(19) C15 0.062(3) 0.057(3) 0.058(3) -0.015(2) 0.003(2) -0.002(2) C16 0.073(3) 0.060(3) 0.055(3) -0.011(2) 0.001(2) -0.004(2) C17 0.147(6) 0.071(4) 0.065(3) -0.008(3) 0.022(4) 0.009(4) C18 0.195(8) 0.080(4) 0.069(4) 0.005(3) 0.033(4) -0.001(5) C19 0.141(6) 0.076(4) 0.071(3) 0.013(3) 0.005(4) 0.003(4) C20 0.084(4) 0.065(3) 0.071(3) 0.002(3) 0.006(3) 0.008(3) C21 0.058(3) 0.063(3) 0.057(3) -0.002(2) 0.002(2) -0.005(2) O1 0.096(3) 0.0535(19) 0.065(2) -0.0028(15) 0.0147(18) 0.0153(18) _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 1.355(5) . ? C1 C4 1.373(6) . ? C1 H1 0.9300 . ? N1 C2 1.380(5) . ? N1 H2 0.8600 . ? C2 C3 1.378(6) . ? C2 C14 1.438(6) . ? C3 C4 1.429(6) . ? C3 C11 1.510(5) . ? C4 C5 1.471(6) . ? C5 C6 1.390(6) . ? C5 C10 1.403(6) . ? C6 C7 1.388(6) . ? C6 H3 0.9300 . ? C7 C8 1.388(7) . ? C7 H4 0.9300 . ? C8 C9 1.375(8) . ? C8 H5 0.9300 . ? C9 C10 1.371(7) . ? C9 H6 0.9300 . ? C10 H7 0.9300 . ? C11 C12 1.501(6) . ? C11 H8 0.9700 . ? C11 H9 0.9700 . ? C12 C13 1.490(6) . ? C12 H10 0.9700 . ? C12 H11 0.9700 . ? C13 O1 1.437(5) . ? C13 C14 1.507(6) . ? C13 H12 0.9800 . ? C14 C15 1.346(6) . ? C15 C16 1.444(6) . ? C15 H13 0.9300 . ? C16 C17 1.396(6) . ? C16 C21 1.398(6) . ? C17 C18 1.392(8) . ? C17 H14 0.9300 . ? C18 C19 1.372(8) . ? C18 H15 0.9300 . ? C19 C20 1.378(7) . ? C19 H16 0.9300 . ? C20 C21 1.384(6) . ? C20 H17 0.9300 . ? C21 O1 1.365(5) . ? 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 C4 110.1(4) . . ? N1 C1 H1 124.9 . . ? C4 C1 H1 124.9 . . ? C1 N1 C2 108.9(3) . . ? C1 N1 H2 125.5 . . ? C2 N1 H2 125.5 . . ? C3 C2 N1 107.3(4) . . ? C3 C2 C14 126.5(4) . . ? N1 C2 C14 126.2(4) . . ? C2 C3 C4 108.2(4) . . ? C2 C3 C11 120.4(4) . . ? C4 C3 C11 131.4(4) . . ? C1 C4 C3 105.4(4) . . ? C1 C4 C5 124.9(4) . . ? C3 C4 C5 129.6(4) . . ? C6 C5 C10 117.6(4) . . ? C6 C5 C4 122.7(4) . . ? C10 C5 C4 119.7(4) . . ? C7 C6 C5 120.7(5) . . ? C7 C6 H3 119.6 . . ? C5 C6 H3 119.6 . . ? C6 C7 C8 120.7(5) . . ? C6 C7 H4 119.7 . . ? C8 C7 H4 119.7 . . ? C9 C8 C7 118.8(5) . . ? C9 C8 H5 120.6 . . ? C7 C8 H5 120.6 . . ? C10 C9 C8 121.0(5) . . ? C10 C9 H6 119.5 . . ? C8 C9 H6 119.5 . . ? C9 C10 C5 121.2(5) . . ? C9 C10 H7 119.4 . . ? C5 C10 H7 119.4 . . ? C12 C11 C3 111.2(3) . . ? C12 C11 H8 109.4 . . ? C3 C11 H8 109.4 . . ? C12 C11 H9 109.4 . . ? C3 C11 H9 109.4 . . ? H8 C11 H9 108.0 . . ? C13 C12 C11 114.0(4) . . ? C13 C12 H10 108.7 . . ? C11 C12 H10 108.7 . . ? C13 C12 H11 108.7 . . ? C11 C12 H11 108.7 . . ? H10 C12 H11 107.6 . . ? O1 C13 C12 108.7(4) . . ? O1 C13 C14 113.0(4) . . ? C12 C13 C14 113.6(4) . . ? O1 C13 H12 107.1 . . ? C12 C13 H12 107.1 . . ? C14 C13 H12 107.1 . . ? C15 C14 C2 127.4(4) . . ? C15 C14 C13 120.8(4) . . ? C2 C14 C13 111.8(3) . . ? C14 C15 C16 120.2(4) . . ? C14 C15 H13 119.9 . . ? C16 C15 H13 119.9 . . ? C17 C16 C21 117.5(5) . . ? C17 C16 C15 123.8(4) . . ? C21 C16 C15 118.7(4) . . ? C18 C17 C16 121.6(5) . . ? C18 C17 H14 119.2 . . ? C16 C17 H14 119.2 . . ? C19 C18 C17 119.1(5) . . ? C19 C18 H15 120.4 . . ? C17 C18 H15 120.4 . . ? C18 C19 C20 120.9(6) . . ? C18 C19 H16 119.6 . . ? C20 C19 H16 119.6 . . ? C19 C20 C21 119.9(5) . . ? C19 C20 H17 120.1 . . ? C21 C20 H17 120.1 . . ? O1 C21 C20 118.2(4) . . ? O1 C21 C16 120.5(4) . . ? C20 C21 C16 121.0(4) . . ? C21 O1 C13 119.7(3) . . ? 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 C4 C1 N1 C2 -0.7(5) . . . . ? C1 N1 C2 C3 0.2(5) . . . . ? C1 N1 C2 C14 179.3(4) . . . . ? N1 C2 C3 C4 0.3(4) . . . . ? C14 C2 C3 C4 -178.8(4) . . . . ? N1 C2 C3 C11 179.3(4) . . . . ? C14 C2 C3 C11 0.2(6) . . . . ? N1 C1 C4 C3 0.8(5) . . . . ? N1 C1 C4 C5 179.1(4) . . . . ? C2 C3 C4 C1 -0.7(5) . . . . ? C11 C3 C4 C1 -179.6(4) . . . . ? C2 C3 C4 C5 -178.9(4) . . . . ? C11 C3 C4 C5 2.2(7) . . . . ? C1 C4 C5 C6 -154.4(4) . . . . ? C3 C4 C5 C6 23.5(7) . . . . ? C1 C4 C5 C10 23.6(6) . . . . ? C3 C4 C5 C10 -158.5(4) . . . . ? C10 C5 C6 C7 -0.2(7) . . . . ? C4 C5 C6 C7 177.8(4) . . . . ? C5 C6 C7 C8 0.2(7) . . . . ? C6 C7 C8 C9 -0.5(8) . . . . ? C7 C8 C9 C10 0.8(9) . . . . ? C8 C9 C10 C5 -0.9(8) . . . . ? C6 C5 C10 C9 0.6(7) . . . . ? C4 C5 C10 C9 -177.5(5) . . . . ? C2 C3 C11 C12 -15.7(6) . . . . ? C4 C3 C11 C12 163.0(4) . . . . ? C3 C11 C12 C13 43.1(5) . . . . ? C11 C12 C13 O1 176.7(4) . . . . ? C11 C12 C13 C14 -56.6(5) . . . . ? C3 C2 C14 C15 170.4(4) . . . . ? N1 C2 C14 C15 -8.6(7) . . . . ? C3 C2 C14 C13 -11.3(6) . . . . ? N1 C2 C14 C13 169.7(4) . . . . ? O1 C13 C14 C15 -18.8(6) . . . . ? C12 C13 C14 C15 -143.2(4) . . . . ? O1 C13 C14 C2 162.8(4) . . . . ? C12 C13 C14 C2 38.3(5) . . . . ? C2 C14 C15 C16 178.9(4) . . . . ? C13 C14 C15 C16 0.7(7) . . . . ? C14 C15 C16 C17 -173.4(5) . . . . ? C14 C15 C16 C21 6.3(7) . . . . ? C21 C16 C17 C18 -1.3(9) . . . . ? C15 C16 C17 C18 178.4(6) . . . . ? C16 C17 C18 C19 0.6(12) . . . . ? C17 C18 C19 C20 0.8(12) . . . . ? C18 C19 C20 C21 -1.4(10) . . . . ? C19 C20 C21 O1 175.1(5) . . . . ? C19 C20 C21 C16 0.6(8) . . . . ? C17 C16 C21 O1 -173.6(5) . . . . ? C15 C16 C21 O1 6.6(7) . . . . ? C17 C16 C21 C20 0.7(8) . . . . ? C15 C16 C21 C20 -179.0(5) . . . . ? C20 C21 O1 C13 158.7(5) . . . . ? C16 C21 O1 C13 -26.8(7) . . . . ? C12 C13 O1 C21 158.7(4) . . . . ? C14 C13 O1 C21 31.7(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.245 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.052