data_publication_text _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Professor Shahriar Mobashery' _publ_contact_author_address ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; _publ_contact_author_email mobashery@nd.edu _publ_contact_author_phone 1(574)6312933 _publ_contact_author_fax 1(574)6316652 loop_ _publ_author_name _publ_author_address 'Hesek, Dusan' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Lee, Mijoon' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Noll, Bruce C.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Fisher, Jed F.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; ' Mobashery, Shahriar' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; data_compound_7 # local ID: dh71_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2' _chemical_formula_sum 'C18 H20 N2' _chemical_formula_weight 264.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0162(4) _cell_length_b 9.5201(4) _cell_length_c 9.5212(4) _cell_angle_alpha 111.414(2) _cell_angle_beta 99.719(2) _cell_angle_gamma 91.631(2) _cell_volume 746.29(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5902 _cell_measurement_theta_min 5.0008 _cell_measurement_theta_max 68.7441 _exptl_crystal_description plate _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details 'Sheldrick, G. M. (2008) SADABS. UNiversity of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFCU2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 9428 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.00 _diffrn_reflns_theta_max 69.46 _reflns_number_total 2631 _reflns_number_gt 2470 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Bruker-Nonius AXS. (2007). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA. CCDC. (2005). enCIFer. The Cambridge Crystallographic Data Centre, Cambridge, UK. Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)' _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^)+(0.0494P)^2^+0.2799P] 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 2631 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _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 N1 N 0.67846(11) 0.59982(10) 0.83903(10) 0.0203(2) Uani 1 1 d . . . N2 N 0.84485(17) 0.66689(15) 0.54660(15) 0.0480(4) Uani 1 1 d . . . C1 C 0.89025(13) 0.67607(13) 1.06033(13) 0.0216(3) Uani 1 1 d . . . C2 C 0.90699(14) 0.70405(13) 1.21643(13) 0.0231(3) Uani 1 1 d . . . H2 H 0.8501 0.6430 1.2489 0.028 Uiso 1 1 calc R . . C3 C 1.00805(14) 0.82251(14) 1.32461(14) 0.0252(3) Uani 1 1 d . . . H3 H 1.0181 0.8404 1.4287 0.030 Uiso 1 1 calc R . . C4 C 1.09360(14) 0.91365(14) 1.27716(14) 0.0265(3) Uani 1 1 d . . . H4 H 1.1611 0.9929 1.3491 0.032 Uiso 1 1 calc R . . C5 C 1.07802(14) 0.88597(14) 1.12125(15) 0.0274(3) Uani 1 1 d . . . H5 H 1.1357 0.9466 1.0889 0.033 Uiso 1 1 calc R . . C6 C 0.97677(14) 0.76829(14) 1.01368(14) 0.0250(3) Uani 1 1 d . . . H6 H 0.9666 0.7509 0.9097 0.030 Uiso 1 1 calc R . . C7 C 0.78167(14) 0.54707(13) 0.94177(13) 0.0225(3) Uani 1 1 d . . . H7B H 0.8385 0.4702 0.8815 0.027 Uiso 1 1 calc R . . H7A H 0.7234 0.5012 0.9935 0.027 Uiso 1 1 calc R . . C8 C 0.53660(15) 0.33737(14) 0.70231(14) 0.0295(3) Uani 1 1 d . . . H8A H 0.6133 0.2870 0.7429 0.044 Uiso 1 1 calc R . . H8B H 0.4862 0.2701 0.6018 0.044 Uiso 1 1 calc R . . H8C H 0.4646 0.3659 0.7690 0.044 Uiso 1 1 calc R . . C9 C 0.60943(14) 0.47919(13) 0.69158(13) 0.0227(3) Uani 1 1 d . . . H9 H 0.5294 0.5222 0.6413 0.027 Uiso 1 1 calc R . . C10 C 0.72655(15) 0.43468(14) 0.58690(14) 0.0258(3) Uani 1 1 d . . . H10A H 0.8060 0.3885 0.6318 0.031 Uiso 1 1 calc R . . H10B H 0.6782 0.3599 0.4878 0.031 Uiso 1 1 calc R . . C11 C 0.79400(16) 0.56504(15) 0.56442(14) 0.0309(3) Uani 1 1 d . . . C12 C 0.56584(14) 0.68650(13) 0.91936(13) 0.0231(3) Uani 1 1 d . . . H12A H 0.6159 0.7535 1.0217 0.028 Uiso 1 1 calc R . . H12B H 0.4925 0.6167 0.9305 0.028 Uiso 1 1 calc R . . C13 C 0.48339(14) 0.77991(13) 0.83836(13) 0.0230(3) Uani 1 1 d . . . C14 C 0.56054(14) 0.85806(13) 0.77003(14) 0.0261(3) Uani 1 1 d . . . H14 H 0.6628 0.8484 0.7693 0.031 Uiso 1 1 calc R . . C15 C 0.48608(16) 0.95039(14) 0.70287(15) 0.0309(3) Uani 1 1 d . . . H15 H 0.5388 1.0021 0.6576 0.037 Uiso 1 1 calc R . . C16 C 0.33355(17) 0.96583(14) 0.70308(15) 0.0336(3) Uani 1 1 d . . . H16 H 0.2841 1.0284 0.6589 0.040 Uiso 1 1 calc R . . C17 C 0.25550(16) 0.88765(16) 0.76929(15) 0.0353(3) Uani 1 1 d . . . H17 H 0.1531 0.8971 0.7692 0.042 Uiso 1 1 calc R . . C18 C 0.33003(15) 0.79484(15) 0.83608(14) 0.0302(3) Uani 1 1 d . . . H18 H 0.2766 0.7420 0.8798 0.036 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 N1 0.0207(5) 0.0204(5) 0.0185(5) 0.0061(4) 0.0026(4) 0.0041(4) N2 0.0645(10) 0.0437(8) 0.0408(7) 0.0160(6) 0.0243(6) -0.0022(6) C1 0.0185(6) 0.0233(6) 0.0224(6) 0.0077(5) 0.0032(4) 0.0078(4) C2 0.0210(6) 0.0258(6) 0.0243(6) 0.0107(5) 0.0055(5) 0.0069(5) C3 0.0241(7) 0.0298(6) 0.0200(6) 0.0072(5) 0.0034(5) 0.0099(5) C4 0.0209(7) 0.0264(6) 0.0258(6) 0.0041(5) 0.0004(5) 0.0038(5) C5 0.0229(7) 0.0298(6) 0.0301(7) 0.0116(5) 0.0060(5) 0.0016(5) C6 0.0248(7) 0.0299(6) 0.0211(6) 0.0101(5) 0.0046(5) 0.0051(5) C7 0.0239(7) 0.0224(6) 0.0222(6) 0.0099(5) 0.0040(5) 0.0034(5) C8 0.0336(7) 0.0246(6) 0.0249(6) 0.0059(5) 0.0004(5) -0.0029(5) C9 0.0245(6) 0.0220(6) 0.0196(6) 0.0066(5) 0.0021(5) 0.0032(5) C10 0.0303(7) 0.0250(6) 0.0210(6) 0.0070(5) 0.0050(5) 0.0075(5) C11 0.0364(8) 0.0337(7) 0.0219(6) 0.0075(5) 0.0102(5) 0.0056(6) C12 0.0229(6) 0.0255(6) 0.0191(6) 0.0060(5) 0.0045(4) 0.0028(5) C13 0.0248(7) 0.0206(6) 0.0167(5) 0.0000(5) 0.0013(4) 0.0055(4) C14 0.0227(7) 0.0200(6) 0.0300(6) 0.0049(5) 0.0006(5) 0.0016(5) C15 0.0366(8) 0.0188(6) 0.0324(7) 0.0068(5) 0.0002(5) 0.0016(5) C16 0.0417(8) 0.0249(6) 0.0259(7) 0.0030(5) -0.0021(6) 0.0149(5) C17 0.0294(8) 0.0447(8) 0.0267(7) 0.0063(6) 0.0051(5) 0.0199(6) C18 0.0276(7) 0.0384(7) 0.0230(6) 0.0078(5) 0.0082(5) 0.0107(5) _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 N1 C12 1.4650(15) . ? N1 C7 1.4673(14) . ? N1 C9 1.4711(15) . ? N2 C11 1.1403(18) . ? C1 C2 1.3913(17) . ? C1 C6 1.3925(17) . ? C1 C7 1.5123(16) . ? C2 C3 1.3926(17) . ? C2 H2 0.9300 . ? C3 C4 1.3847(18) . ? C3 H3 0.9300 . ? C4 C5 1.3909(18) . ? C4 H4 0.9300 . ? C5 C6 1.3877(18) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C8 C9 1.5289(16) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.5364(17) . ? C9 H9 0.9800 . ? C10 C11 1.4666(18) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C13 1.5110(16) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.3914(19) . ? C13 C14 1.3919(18) . ? C14 C15 1.3897(18) . ? C14 H14 0.9300 . ? C15 C16 1.388(2) . ? C15 H15 0.9300 . ? C16 C17 1.382(2) . ? C16 H16 0.9300 . ? C17 C18 1.3916(19) . ? C17 H17 0.9300 . ? C18 H18 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 C12 N1 C7 110.55(9) . . ? C12 N1 C9 112.49(9) . . ? C7 N1 C9 114.01(9) . . ? C2 C1 C6 118.88(11) . . ? C2 C1 C7 121.18(11) . . ? C6 C1 C7 119.94(10) . . ? C1 C2 C3 120.72(11) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 119.99(11) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.63(11) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 120.29(12) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 120.48(11) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N1 C7 C1 111.39(9) . . ? N1 C7 H7B 109.4 . . ? C1 C7 H7B 109.4 . . ? N1 C7 H7A 109.4 . . ? C1 C7 H7A 109.4 . . ? H7B C7 H7A 108.0 . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C8 115.73(9) . . ? N1 C9 C10 109.81(10) . . ? C8 C9 C10 109.77(10) . . ? N1 C9 H9 107.0 . . ? C8 C9 H9 107.0 . . ? C10 C9 H9 107.0 . . ? C11 C10 C9 112.40(10) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? N2 C11 C10 179.22(16) . . ? N1 C12 C13 113.70(9) . . ? N1 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N1 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C18 C13 C14 118.54(11) . . ? C18 C13 C12 120.70(11) . . ? C14 C13 C12 120.71(11) . . ? C15 C14 C13 120.57(12) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.33(13) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.59(12) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.04(13) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C13 C18 C17 120.92(13) . . ? C13 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 69.46 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.239 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.039 _chemical_compound_source synthesized