# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_s #TrackingRef '18048_web_deposit_cif_file_0_LingliangLong_1361943532.1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N2 O2' _chemical_formula_weight 320.38 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 P21/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 8.2474(16) _cell_length_b 17.675(3) _cell_length_c 11.501(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.32(3) _cell_angle_gamma 90.00 _cell_volume 1643.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 7721 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3190 _reflns_number_gt 2562 _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^)+(0.0469P)^2^+0.4402P] 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 3190 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1128 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 -0.73443(15) 0.09952(6) -0.04706(10) 0.0303(3) Uani 1 1 d . . . O2 O -0.64222(18) 0.08704(7) -0.21217(11) 0.0397(4) Uani 1 1 d . . . N1 N -0.5209(2) -0.23111(9) -0.55757(14) 0.0343(4) Uani 1 1 d . . . N2 N -0.92242(19) 0.15017(9) 0.31073(14) 0.0349(4) Uani 1 1 d . . . C1 C -0.5071(2) -0.24790(11) -0.44257(17) 0.0330(5) Uani 1 1 d . . . H1B H -0.4809 -0.2975 -0.4192 0.040 Uiso 1 1 calc R . . C2 C -0.5290(2) -0.19680(10) -0.35618(16) 0.0289(4) Uani 1 1 d . . . H2A H -0.5170 -0.2122 -0.2776 0.035 Uiso 1 1 calc R . . C3 C -0.5692(2) -0.12180(10) -0.38766(16) 0.0266(4) Uani 1 1 d . . . C4 C -0.5830(2) -0.10407(10) -0.50718(16) 0.0296(4) Uani 1 1 d . . . H4A H -0.6092 -0.0550 -0.5333 0.036 Uiso 1 1 calc R . . C5 C -0.5578(2) -0.15899(11) -0.58694(17) 0.0337(5) Uani 1 1 d . . . H5A H -0.5671 -0.1451 -0.6659 0.040 Uiso 1 1 calc R . . C6 C -0.6010(2) -0.06427(10) -0.30352(15) 0.0275(4) Uani 1 1 d . . . H6A H -0.5989 -0.0138 -0.3260 0.033 Uiso 1 1 calc R . . C7 C -0.6331(2) -0.07947(10) -0.19615(16) 0.0276(4) Uani 1 1 d . . . H7A H -0.6235 -0.1300 -0.1732 0.033 Uiso 1 1 calc R . . C8 C -0.6806(2) -0.02783(10) -0.11096(15) 0.0262(4) Uani 1 1 d . . . C9 C -0.7292(2) -0.05424(10) -0.01184(16) 0.0281(4) Uani 1 1 d . . . H9A H -0.7283 -0.1062 0.0011 0.034 Uiso 1 1 calc R . . C10 C -0.7811(2) -0.00621(10) 0.07242(16) 0.0276(4) Uani 1 1 d . . . C11 C -0.7815(2) 0.07152(10) 0.05303(15) 0.0261(4) Uani 1 1 d . . . C12 C -0.6826(2) 0.05392(10) -0.13057(16) 0.0284(4) Uani 1 1 d . . . C13 C -0.8321(2) -0.02980(11) 0.17619(17) 0.0336(5) Uani 1 1 d . . . H13A H -0.8342 -0.0813 0.1927 0.040 Uiso 1 1 calc R . . C14 C -0.8785(2) 0.02043(11) 0.25341(17) 0.0347(5) Uani 1 1 d . . . H14A H -0.9116 0.0025 0.3211 0.042 Uiso 1 1 calc R . . C15 C -0.8775(2) 0.09970(10) 0.23254(16) 0.0294(4) Uani 1 1 d . . . C16 C -0.8274(2) 0.12406(10) 0.12866(16) 0.0293(4) Uani 1 1 d . . . H16A H -0.8253 0.1754 0.1112 0.035 Uiso 1 1 calc R . . C17 C -0.9921(2) 0.12562(12) 0.41174(17) 0.0366(5) Uani 1 1 d . . . H17A H -1.0558 0.0798 0.3904 0.044 Uiso 1 1 calc R . . H17B H -1.0670 0.1643 0.4295 0.044 Uiso 1 1 calc R . . C18 C -0.8622(3) 0.11058(14) 0.52145(18) 0.0466(6) Uani 1 1 d . . . H18A H -0.9148 0.0943 0.5846 0.070 Uiso 1 1 calc R . . H18B H -0.8008 0.1561 0.5446 0.070 Uiso 1 1 calc R . . H18C H -0.7886 0.0717 0.5049 0.070 Uiso 1 1 calc R . . C19 C -0.9138(2) 0.23161(11) 0.29252(18) 0.0370(5) Uani 1 1 d . . . H19A H -0.8198 0.2428 0.2563 0.044 Uiso 1 1 calc R . . H19B H -0.8965 0.2569 0.3688 0.044 Uiso 1 1 calc R . . C20 C -1.0688(3) 0.26238(12) 0.2147(2) 0.0486(6) Uani 1 1 d . . . H20A H -1.0580 0.3160 0.2059 0.073 Uiso 1 1 calc R . . H20B H -1.1621 0.2520 0.2506 0.073 Uiso 1 1 calc R . . H20C H -1.0847 0.2386 0.1382 0.073 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 0.0424(7) 0.0217(6) 0.0286(7) 0.0012(5) 0.0110(6) -0.0002(6) O2 0.0651(10) 0.0256(7) 0.0319(7) 0.0014(6) 0.0184(7) -0.0042(7) N1 0.0375(9) 0.0311(9) 0.0343(9) -0.0063(7) 0.0066(7) -0.0003(7) N2 0.0385(9) 0.0360(9) 0.0322(9) -0.0001(7) 0.0121(7) 0.0059(7) C1 0.0335(10) 0.0267(10) 0.0379(12) -0.0005(8) 0.0044(9) 0.0020(8) C2 0.0293(9) 0.0286(9) 0.0279(10) 0.0005(8) 0.0036(8) 0.0025(8) C3 0.0211(9) 0.0259(9) 0.0322(10) -0.0009(8) 0.0036(8) -0.0018(7) C4 0.0300(9) 0.0264(9) 0.0315(10) 0.0014(8) 0.0036(8) -0.0008(8) C5 0.0355(11) 0.0359(11) 0.0299(10) -0.0035(8) 0.0070(9) -0.0045(9) C6 0.0282(9) 0.0225(9) 0.0305(10) -0.0006(7) 0.0025(8) 0.0005(7) C7 0.0286(9) 0.0221(9) 0.0306(10) -0.0009(8) 0.0020(8) 0.0004(7) C8 0.0255(9) 0.0230(9) 0.0282(10) 0.0002(7) 0.0005(8) -0.0017(7) C9 0.0293(9) 0.0212(9) 0.0321(10) 0.0024(8) 0.0016(8) -0.0010(7) C10 0.0280(9) 0.0254(9) 0.0286(10) 0.0013(8) 0.0033(8) -0.0007(8) C11 0.0274(9) 0.0265(9) 0.0234(9) 0.0031(7) 0.0023(8) -0.0013(7) C12 0.0351(10) 0.0237(9) 0.0257(10) -0.0031(8) 0.0047(8) -0.0025(8) C13 0.0388(11) 0.0269(10) 0.0352(11) 0.0050(8) 0.0077(9) -0.0005(8) C14 0.0386(11) 0.0358(11) 0.0316(10) 0.0055(9) 0.0112(9) 0.0033(9) C15 0.0242(9) 0.0341(10) 0.0290(10) -0.0003(8) 0.0027(8) 0.0027(8) C16 0.0303(9) 0.0248(9) 0.0318(10) 0.0009(8) 0.0040(8) 0.0015(8) C17 0.0313(10) 0.0463(12) 0.0337(11) -0.0030(9) 0.0100(9) 0.0017(9) C18 0.0404(12) 0.0634(15) 0.0355(12) 0.0019(10) 0.0061(10) 0.0007(11) C19 0.0390(11) 0.0350(11) 0.0384(12) -0.0087(9) 0.0110(9) 0.0006(9) C20 0.0441(12) 0.0402(12) 0.0632(15) 0.0029(11) 0.0147(11) 0.0103(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.377(2) . ? O1 C12 1.384(2) . ? O2 C12 1.207(2) . ? N1 C5 1.338(2) . ? N1 C1 1.338(2) . ? N2 C15 1.368(2) . ? N2 C19 1.458(2) . ? N2 C17 1.459(2) . ? C1 C2 1.380(2) . ? C1 H1B 0.9300 . ? C2 C3 1.397(2) . ? C2 H2A 0.9300 . ? C3 C4 1.393(3) . ? C3 C6 1.462(2) . ? C4 C5 1.379(2) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.340(2) . ? C6 H6A 0.9300 . ? C7 C8 1.448(2) . ? C7 H7A 0.9300 . ? C8 C9 1.363(2) . ? C8 C12 1.462(2) . ? C9 C10 1.416(3) . ? C9 H9A 0.9300 . ? C10 C11 1.392(2) . ? C10 C13 1.404(3) . ? C11 C16 1.375(2) . ? C13 C14 1.363(3) . ? C13 H13A 0.9300 . ? C14 C15 1.422(3) . ? C14 H14A 0.9300 . ? C15 C16 1.406(3) . ? C16 H16A 0.9300 . ? C17 C18 1.510(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.510(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C11 O1 C12 123.16(14) . . ? C5 N1 C1 115.57(16) . . ? C15 N2 C19 121.47(16) . . ? C15 N2 C17 121.94(16) . . ? C19 N2 C17 116.46(16) . . ? N1 C1 C2 124.64(17) . . ? N1 C1 H1B 117.7 . . ? C2 C1 H1B 117.7 . . ? C1 C2 C3 119.49(17) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C4 C3 C2 116.01(16) . . ? C4 C3 C6 120.42(16) . . ? C2 C3 C6 123.55(16) . . ? C5 C4 C3 120.29(17) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? N1 C5 C4 123.99(18) . . ? N1 C5 H5A 118.0 . . ? C4 C5 H5A 118.0 . . ? C7 C6 C3 124.33(17) . . ? C7 C6 H6A 117.8 . . ? C3 C6 H6A 117.8 . . ? C6 C7 C8 128.75(17) . . ? C6 C7 H7A 115.6 . . ? C8 C7 H7A 115.6 . . ? C9 C8 C7 120.88(16) . . ? C9 C8 C12 118.13(16) . . ? C7 C8 C12 120.97(16) . . ? C8 C9 C10 123.02(16) . . ? C8 C9 H9A 118.5 . . ? C10 C9 H9A 118.5 . . ? C11 C10 C13 115.95(17) . . ? C11 C10 C9 118.28(16) . . ? C13 C10 C9 125.77(17) . . ? C16 C11 O1 116.35(15) . . ? C16 C11 C10 123.89(17) . . ? O1 C11 C10 119.77(16) . . ? O2 C12 O1 115.28(15) . . ? O2 C12 C8 127.08(17) . . ? O1 C12 C8 117.63(15) . . ? C14 C13 C10 121.98(17) . . ? C14 C13 H13A 119.0 . . ? C10 C13 H13A 119.0 . . ? C13 C14 C15 121.35(18) . . ? C13 C14 H14A 119.3 . . ? C15 C14 H14A 119.3 . . ? N2 C15 C16 121.42(17) . . ? N2 C15 C14 121.34(17) . . ? C16 C15 C14 117.24(17) . . ? C11 C16 C15 119.59(17) . . ? C11 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? N2 C17 C18 113.10(16) . . ? N2 C17 H17A 109.0 . . ? C18 C17 H17A 109.0 . . ? N2 C17 H17B 109.0 . . ? C18 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C20 112.41(17) . . ? N2 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? N2 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.4(3) . . . . ? N1 C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C1 C2 C3 C6 177.58(16) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C6 C3 C4 C5 -178.03(16) . . . . ? C1 N1 C5 C4 -0.8(3) . . . . ? C3 C4 C5 N1 0.5(3) . . . . ? C4 C3 C6 C7 161.88(17) . . . . ? C2 C3 C6 C7 -16.2(3) . . . . ? C3 C6 C7 C8 -173.83(16) . . . . ? C6 C7 C8 C9 171.49(18) . . . . ? C6 C7 C8 C12 -6.7(3) . . . . ? C7 C8 C9 C10 -178.26(16) . . . . ? C12 C8 C9 C10 0.0(3) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C8 C9 C10 C13 -179.84(18) . . . . ? C12 O1 C11 C16 178.96(15) . . . . ? C12 O1 C11 C10 -1.2(2) . . . . ? C13 C10 C11 C16 0.3(3) . . . . ? C9 C10 C11 C16 -179.30(16) . . . . ? C13 C10 C11 O1 -179.52(15) . . . . ? C9 C10 C11 O1 0.9(2) . . . . ? C11 O1 C12 O2 -178.57(15) . . . . ? C11 O1 C12 C8 0.9(2) . . . . ? C9 C8 C12 O2 179.13(18) . . . . ? C7 C8 C12 O2 -2.6(3) . . . . ? C9 C8 C12 O1 -0.2(2) . . . . ? C7 C8 C12 O1 178.00(15) . . . . ? C11 C10 C13 C14 -0.3(3) . . . . ? C9 C10 C13 C14 179.28(18) . . . . ? C10 C13 C14 C15 0.0(3) . . . . ? C19 N2 C15 C16 -2.6(3) . . . . ? C17 N2 C15 C16 173.02(16) . . . . ? C19 N2 C15 C14 176.98(17) . . . . ? C17 N2 C15 C14 -7.4(3) . . . . ? C13 C14 C15 N2 -179.28(17) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? O1 C11 C16 C15 179.81(15) . . . . ? C10 C11 C16 C15 0.0(3) . . . . ? N2 C15 C16 C11 179.29(16) . . . . ? C14 C15 C16 C11 -0.3(3) . . . . ? C15 N2 C17 C18 89.1(2) . . . . ? C19 N2 C17 C18 -95.1(2) . . . . ? C15 N2 C19 C20 86.6(2) . . . . ? C17 N2 C19 C20 -89.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.196 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 926760'