# 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_red _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 N2' _chemical_formula_sum 'C24 H26 N2' _chemical_formula_weight 342.47 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 Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 12.8233(9) _cell_length_b 16.9231(15) _cell_length_c 9.0073(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1954.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1800 _cell_measurement_theta_min 2.8930 _cell_measurement_theta_max 21.6720 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9826 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'CrysAlisPro, Agilent Technologies' _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 'Xcalibur, Eos, Nova' _diffrn_measurement_method 'f\w scans' _diffrn_detector_area_resol_mean 16.0839 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8890 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3447 _reflns_number_gt 2125 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Agilent Technologies)' _computing_cell_refinement 'CrysAlisPro (Agilent Technologies)' _computing_data_reduction 'CrysAlisPro (Agilent Technologies)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0874P)^2^+0.0000P] 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 7(6) _refine_ls_number_reflns 3200 _refine_ls_number_parameters 240 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.2001 _refine_ls_wR_factor_gt 0.1575 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 -0.8614(3) -0.0393(3) -0.4033(5) 0.0551(11) Uani 1 1 d . . . C1A C -0.8218(4) -0.1980(3) 0.0011(5) 0.0739(15) Uani 1 1 d . . . H1AA H -0.8348 -0.1580 0.0742 0.111 Uiso 1 1 calc R . . H1AB H -0.7913 -0.2434 0.0481 0.111 Uiso 1 1 calc R . . H1AC H -0.8863 -0.2129 -0.0452 0.111 Uiso 1 1 calc R . . C1B C -0.7463(5) -0.2059(3) -0.5300(5) 0.0863(17) Uani 1 1 d . . . H1BA H -0.6829 -0.1759 -0.5274 0.129 Uiso 1 1 calc R . . H1BB H -0.7895 -0.1873 -0.6097 0.129 Uiso 1 1 calc R . . H1BC H -0.7303 -0.2607 -0.5452 0.129 Uiso 1 1 calc R . . C1C C -0.9090(4) -0.2407(3) -0.3914(7) 0.0832(16) Uani 1 1 d . . . H1CA H -0.9530 -0.2160 -0.4641 0.125 Uiso 1 1 calc R . . H1CB H -0.9426 -0.2392 -0.2962 0.125 Uiso 1 1 calc R . . H1CC H -0.8965 -0.2946 -0.4193 0.125 Uiso 1 1 calc R . . C2 C -0.5378(3) -0.0763(3) -0.2606(5) 0.0519(10) Uani 1 1 d . . . H2 H -0.5907 -0.0770 -0.3313 0.062 Uiso 1 1 calc R . . C3 C -0.6421(3) -0.1476(2) -0.0485(4) 0.0503(10) Uani 1 1 d . . . C4 C -0.5533(3) -0.1096(2) -0.1199(4) 0.0465(10) Uani 1 1 d . . . C7 C -0.8204(3) -0.1108(3) -0.3421(5) 0.0557(11) Uani 1 1 d . . . C8 C -0.7926(3) -0.0965(2) -0.2011(5) 0.0493(10) Uani 1 1 d . . . C9 C -0.8524(3) 0.0170(3) -0.2882(5) 0.0569(11) Uani 1 1 d . . . C10 C -0.8042(4) -0.1961(3) -0.3827(5) 0.0601(12) Uani 1 1 d . . . C11 C -0.4432(3) -0.0427(3) -0.2917(5) 0.0608(12) Uani 1 1 d . . . H11 H -0.4324 -0.0199 -0.3844 0.073 Uiso 1 1 calc R . . C12 C -0.7357(4) -0.2253(3) -0.2497(5) 0.0623(12) Uani 1 1 d . . . H12A H -0.7587 -0.2773 -0.2183 0.075 Uiso 1 1 calc R . . H12B H -0.6634 -0.2291 -0.2804 0.075 Uiso 1 1 calc R . . C13 C -0.3625(4) -0.0419(3) -0.1879(6) 0.0686(13) Uani 1 1 d . . . H13 H -0.2989 -0.0192 -0.2130 0.082 Uiso 1 1 calc R . . C14 C -0.7459(3) -0.1656(2) -0.1179(4) 0.0520(10) Uani 1 1 d . . . C15 C -0.3756(4) -0.0743(3) -0.0484(5) 0.0613(12) Uani 1 1 d . . . H15 H -0.3220 -0.0735 0.0212 0.074 Uiso 1 1 calc R . . C16 C -0.6076(4) -0.1644(3) 0.0926(5) 0.0612(12) Uani 1 1 d . . . H16 H -0.6483 -0.1881 0.1655 0.073 Uiso 1 1 calc R . . C17 C -0.9009(4) -0.0162(3) -0.5398(6) 0.0690(13) Uani 1 1 d . . . H17 H -0.9085 -0.0528 -0.6160 0.083 Uiso 1 1 calc R . . C18 C -0.4705(3) -0.1078(2) -0.0162(4) 0.0509(10) Uani 1 1 d . . . C19 C -0.7955(4) 0.0190(3) -0.0197(5) 0.0802(16) Uani 1 1 d . . . H19A H -0.7586 -0.0166 0.0445 0.120 Uiso 1 1 calc R . . H19B H -0.8623 0.0310 0.0227 0.120 Uiso 1 1 calc R . . H19C H -0.7561 0.0668 -0.0312 0.120 Uiso 1 1 calc R . . C20 C -0.9292(4) 0.0623(4) -0.5620(8) 0.0866(17) Uani 1 1 d . . . H20 H -0.9557 0.0781 -0.6535 0.104 Uiso 1 1 calc R . . C21 C -0.9183(4) 0.1172(3) -0.4490(8) 0.0850(17) Uani 1 1 d . . . H21 H -0.9369 0.1695 -0.4666 0.102 Uiso 1 1 calc R . . C23 C -0.4486(5) -0.1477(4) 0.2512(5) 0.0842(17) Uani 1 1 d . . . H23A H -0.4875 -0.1790 0.3207 0.126 Uiso 1 1 calc R . . H23B H -0.4381 -0.0957 0.2911 0.126 Uiso 1 1 calc R . . H23C H -0.3822 -0.1722 0.2334 0.126 Uiso 1 1 calc R . . C26 C -0.8802(4) 0.0964(3) -0.3100(7) 0.0736(15) Uani 1 1 d . . . H26 H -0.8733 0.1335 -0.2345 0.088 Uiso 1 1 calc R . . N5 N -0.8101(3) -0.0180(2) -0.1644(4) 0.0554(9) Uani 1 1 d . . . N6 N -0.5057(3) -0.1422(2) 0.1129(4) 0.0586(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 0.045(2) 0.060(3) 0.060(3) -0.002(2) -0.005(2) -0.0009(19) C1A 0.070(3) 0.085(4) 0.067(3) 0.011(3) 0.010(3) -0.012(3) C1B 0.107(5) 0.086(4) 0.066(3) -0.021(3) 0.021(3) -0.001(3) C1C 0.088(4) 0.072(3) 0.090(4) -0.004(3) -0.007(3) -0.029(3) C2 0.054(3) 0.054(2) 0.048(2) 0.004(2) -0.003(2) 0.005(2) C3 0.053(2) 0.049(2) 0.049(2) 0.004(2) 0.009(2) 0.0015(19) C4 0.045(2) 0.046(2) 0.049(2) 0.0015(19) -0.0039(19) 0.0073(18) C7 0.053(3) 0.054(3) 0.060(3) -0.005(2) -0.009(2) -0.003(2) C8 0.047(2) 0.049(2) 0.052(2) -0.004(2) 0.006(2) 0.0029(18) C9 0.043(2) 0.057(3) 0.070(3) -0.003(2) -0.004(2) 0.0002(19) C10 0.071(3) 0.049(3) 0.060(3) -0.010(2) 0.007(2) -0.011(2) C11 0.059(3) 0.069(3) 0.054(3) 0.016(2) 0.005(2) -0.002(2) C12 0.071(3) 0.047(2) 0.069(3) 0.001(2) -0.003(2) 0.004(2) C13 0.060(3) 0.071(3) 0.075(3) 0.000(3) 0.014(3) -0.008(2) C14 0.058(3) 0.047(2) 0.050(2) -0.0006(19) -0.002(2) -0.004(2) C15 0.048(3) 0.073(3) 0.063(3) -0.001(3) -0.002(2) 0.000(2) C16 0.064(3) 0.068(3) 0.052(3) 0.010(2) 0.003(2) 0.000(2) C17 0.057(3) 0.076(3) 0.075(3) 0.006(3) -0.007(3) -0.010(2) C18 0.057(3) 0.053(2) 0.043(2) 0.0061(19) 0.001(2) 0.010(2) C19 0.086(4) 0.079(3) 0.075(3) -0.040(3) -0.021(3) 0.007(3) C20 0.065(3) 0.097(4) 0.098(4) 0.017(4) -0.023(3) -0.006(3) C21 0.062(3) 0.067(3) 0.126(5) 0.025(4) -0.012(4) 0.002(3) C23 0.100(4) 0.104(4) 0.049(3) 0.012(3) -0.020(3) 0.021(3) C26 0.060(3) 0.052(3) 0.108(4) 0.001(3) -0.008(3) 0.004(2) N5 0.053(2) 0.053(2) 0.060(2) -0.0065(19) -0.0041(19) 0.0024(16) N6 0.064(2) 0.067(3) 0.0451(19) 0.0094(18) -0.0089(19) 0.0077(19) _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 C17 1.386(7) . ? C1 C9 1.414(6) . ? C1 C7 1.429(6) . ? C1A C14 1.548(6) . ? C1A H1AA 0.9600 . ? C1A H1AB 0.9600 . ? C1A H1AC 0.9600 . ? C1B C10 1.529(6) . ? C1B H1BA 0.9600 . ? C1B H1BB 0.9600 . ? C1B H1BC 0.9600 . ? C1C C10 1.543(6) . ? C1C H1CA 0.9600 . ? C1C H1CB 0.9600 . ? C1C H1CC 0.9600 . ? C2 C11 1.369(6) . ? C2 C4 1.401(6) . ? C2 H2 0.9300 . ? C3 C16 1.376(6) . ? C3 C4 1.458(6) . ? C3 C14 1.502(6) . ? C4 C18 1.414(5) . ? C7 C8 1.341(6) . ? C7 C10 1.505(6) . ? C8 N5 1.387(5) . ? C8 C14 1.513(6) . ? C9 N5 1.374(5) . ? C9 C26 1.403(6) . ? C10 C12 1.565(6) . ? C11 C13 1.394(7) . ? C11 H11 0.9300 . ? C12 C14 1.564(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.381(6) . ? C13 H13 0.9300 . ? C15 C18 1.374(6) . ? C15 H15 0.9300 . ? C16 N6 1.371(6) . ? C16 H16 0.9300 . ? C17 C20 1.392(8) . ? C17 H17 0.9300 . ? C18 N6 1.376(5) . ? C19 N5 1.458(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.386(8) . ? C20 H20 0.9300 . ? C21 C26 1.389(8) . ? C21 H21 0.9300 . ? C23 N6 1.449(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C26 H26 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 C17 C1 C9 119.4(4) . . ? C17 C1 C7 135.7(4) . . ? C9 C1 C7 104.9(4) . . ? C14 C1A H1AA 109.5 . . ? C14 C1A H1AB 109.5 . . ? H1AA C1A H1AB 109.5 . . ? C14 C1A H1AC 109.5 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? C10 C1B H1BA 109.5 . . ? C10 C1B H1BB 109.5 . . ? H1BA C1B H1BB 109.5 . . ? C10 C1B H1BC 109.5 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? C10 C1C H1CA 109.5 . . ? C10 C1C H1CB 109.5 . . ? H1CA C1C H1CB 109.5 . . ? C10 C1C H1CC 109.5 . . ? H1CA C1C H1CC 109.5 . . ? H1CB C1C H1CC 109.5 . . ? C11 C2 C4 118.5(4) . . ? C11 C2 H2 120.7 . . ? C4 C2 H2 120.7 . . ? C16 C3 C4 104.3(4) . . ? C16 C3 C14 128.9(4) . . ? C4 C3 C14 126.8(4) . . ? C2 C4 C18 118.9(4) . . ? C2 C4 C3 133.4(4) . . ? C18 C4 C3 107.7(3) . . ? C8 C7 C1 108.1(4) . . ? C8 C7 C10 111.5(4) . . ? C1 C7 C10 140.3(4) . . ? C7 C8 N5 110.8(4) . . ? C7 C8 C14 115.8(4) . . ? N5 C8 C14 133.3(4) . . ? N5 C9 C26 128.8(4) . . ? N5 C9 C1 109.6(4) . . ? C26 C9 C1 121.5(4) . . ? C7 C10 C1B 112.5(4) . . ? C7 C10 C1C 111.2(4) . . ? C1B C10 C1C 109.0(4) . . ? C7 C10 C12 101.2(3) . . ? C1B C10 C12 111.0(4) . . ? C1C C10 C12 111.9(4) . . ? C2 C11 C13 121.6(4) . . ? C2 C11 H11 119.2 . . ? C13 C11 H11 119.2 . . ? C14 C12 C10 109.3(3) . . ? C14 C12 H12A 109.8 . . ? C10 C12 H12A 109.8 . . ? C14 C12 H12B 109.8 . . ? C10 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? C15 C13 C11 121.1(4) . . ? C15 C13 H13 119.4 . . ? C11 C13 H13 119.4 . . ? C3 C14 C8 113.6(3) . . ? C3 C14 C1A 109.9(4) . . ? C8 C14 C1A 111.6(4) . . ? C3 C14 C12 111.9(4) . . ? C8 C14 C12 99.0(3) . . ? C1A C14 C12 110.4(3) . . ? C18 C15 C13 117.6(4) . . ? C18 C15 H15 121.2 . . ? C13 C15 H15 121.2 . . ? N6 C16 C3 111.9(4) . . ? N6 C16 H16 124.1 . . ? C3 C16 H16 124.1 . . ? C1 C17 C20 119.5(5) . . ? C1 C17 H17 120.3 . . ? C20 C17 H17 120.3 . . ? C15 C18 N6 130.1(4) . . ? C15 C18 C4 122.3(4) . . ? N6 C18 C4 107.6(4) . . ? N5 C19 H19A 109.5 . . ? N5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C17 120.6(5) . . ? C21 C20 H20 119.7 . . ? C17 C20 H20 119.7 . . ? C20 C21 C26 121.8(5) . . ? C20 C21 H21 119.1 . . ? C26 C21 H21 119.1 . . ? N6 C23 H23A 109.5 . . ? N6 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N6 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C26 C9 117.3(5) . . ? C21 C26 H26 121.3 . . ? C9 C26 H26 121.3 . . ? C9 N5 C8 106.5(3) . . ? C9 N5 C19 126.2(4) . . ? C8 N5 C19 127.1(4) . . ? C16 N6 C18 108.4(3) . . ? C16 N6 C23 125.3(4) . . ? C18 N6 C23 126.0(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.216 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 957557'