# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'S. Trofimenko' 'A. L. Rheingold' 'L. M. Liable-Sands' 'R. M. Claramunt' 'C. Lopez' 'Dolores Santa Maria, M. ' 'J. Elguero' # 1. SUBMISSION DETAILS _publ_contact_author 'Dr. Arnold L. Rheingold and Dr. S. Trofimenko' loop_ _publ_contact_author_address ; Dr. Arnold L. Rheingold Department of Chemistry and Biochemistry University of Delaware, Newark, DE 19716 USA ; ; Dr. S. Trofimenko Department of Chemistry and Biochemistry University of Delaware, Newark, DE 19716 USA ; _publ_contact_author_phone '+302 831 8720' _publ_contact_author_fax '+302 831 6335' _publ_contact_author_email arnrhein@udel.edu data_trof57 _database_code_CSD 163025 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 N2' _chemical_formula_weight 214.30 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7417(2) _cell_length_b 15.7638(2) _cell_length_c 16.3452(2) _cell_angle_alpha 61.8921(3) _cell_angle_beta 88.7569(8) _cell_angle_gamma 78.1825(9) _cell_volume 2602.20(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9682 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15322 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0962 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 26.00 _reflns_number_total 9740 _reflns_number_gt 5985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9740 _refine_ls_number_parameters 593 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1115 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.2059 _refine_ls_wR_factor_gt 0.1678 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 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 N1A N 0.3115(2) 0.46957(16) 0.45971(15) 0.0325(5) Uani 1 1 d . . . N2A N 0.37582(19) 0.38029(15) 0.52357(13) 0.0295(5) Uani 1 1 d . . . C1A C 0.4054(2) 0.21731(18) 0.73623(17) 0.0321(6) Uani 1 1 d . . . H1AB H 0.3274 0.2208 0.7183 0.039 Uiso 1 1 calc R . . C2A C 0.4682(3) 0.1317(2) 0.81251(18) 0.0371(7) Uani 1 1 d . . . H2AB H 0.4322 0.0773 0.8445 0.045 Uiso 1 1 calc R . . C3A C 0.5815(3) 0.12385(19) 0.84291(17) 0.0340(7) Uani 1 1 d . . . C4A C 0.6314(3) 0.2054(2) 0.79407(18) 0.0360(7) Uani 1 1 d . . . H4AA H 0.7080 0.2030 0.8138 0.043 Uiso 1 1 calc R . . C5A C 0.5704(2) 0.29084(19) 0.71642(17) 0.0317(6) Uani 1 1 d . . . H5AA H 0.6071 0.3447 0.6840 0.038 Uiso 1 1 calc R . . C6A C 0.4575(2) 0.29808(17) 0.68613(16) 0.0258(6) Uani 1 1 d . . . C7A C 0.6499(3) 0.0299(2) 0.92449(19) 0.0499(8) Uani 1 1 d . . . H7AA H 0.7275 0.0387 0.9350 0.075 Uiso 1 1 calc R . . H7AB H 0.6580 -0.0250 0.9105 0.075 Uiso 1 1 calc R . . H7AC H 0.6082 0.0154 0.9805 0.075 Uiso 1 1 calc R . . C8A C 0.3917(2) 0.38760(18) 0.60211(16) 0.0257(6) Uani 1 1 d . . . C9A C 0.3364(2) 0.48302(18) 0.58820(16) 0.0264(6) Uani 1 1 d . . . C10A C 0.2878(2) 0.53157(19) 0.49661(17) 0.0327(6) Uani 1 1 d . . . H10C H 0.2446 0.5979 0.4649 0.039 Uiso 1 1 calc R . . C11A C 0.3265(2) 0.52468(18) 0.65678(17) 0.0293(6) Uani 1 1 d . . . C12A C 0.2714(3) 0.4573(2) 0.74409(18) 0.0391(7) Uani 1 1 d . . . H12G H 0.3214 0.3908 0.7740 0.059 Uiso 1 1 calc R . . H12H H 0.1940 0.4545 0.7257 0.059 Uiso 1 1 calc R . . H12I H 0.2641 0.4839 0.7878 0.059 Uiso 1 1 calc R . . C13A C 0.4458(2) 0.5320(2) 0.68614(18) 0.0365(7) Uani 1 1 d . . . H13G H 0.4807 0.5747 0.6309 0.055 Uiso 1 1 calc R . . H13H H 0.4972 0.4661 0.7173 0.055 Uiso 1 1 calc R . . H13I H 0.4357 0.5599 0.7289 0.055 Uiso 1 1 calc R . . C14A C 0.2463(3) 0.6291(2) 0.6109(2) 0.0451(8) Uani 1 1 d . . . H14G H 0.2800 0.6727 0.5554 0.068 Uiso 1 1 calc R . . H14H H 0.2392 0.6550 0.6552 0.068 Uiso 1 1 calc R . . H14I H 0.1688 0.6258 0.5930 0.068 Uiso 1 1 calc R . . N1B N 0.46785(19) 0.30058(15) 0.23367(15) 0.0298(5) Uani 1 1 d . . . N2B N 0.38258(19) 0.37902(15) 0.17578(13) 0.0286(5) Uani 1 1 d . . . C1B C 0.3174(2) 0.54519(18) -0.05054(17) 0.0304(6) Uani 1 1 d . . . H1BB H 0.3910 0.5593 -0.0455 0.036 Uiso 1 1 calc R . . C2B C 0.2335(2) 0.6151(2) -0.12218(18) 0.0351(7) Uani 1 1 d . . . H2BB H 0.2507 0.6767 -0.1642 0.042 Uiso 1 1 calc R . . C3B C 0.1251(2) 0.5971(2) -0.13400(17) 0.0349(7) Uani 1 1 d . . . C4B C 0.1032(2) 0.5051(2) -0.07089(18) 0.0385(7) Uani 1 1 d . . . H4BA H 0.0310 0.4899 -0.0779 0.046 Uiso 1 1 calc R . . C5B C 0.1860(2) 0.4353(2) 0.00221(18) 0.0338(6) Uani 1 1 d . . . H5BA H 0.1684 0.3739 0.0444 0.041 Uiso 1 1 calc R . . C6B C 0.2938(2) 0.45384(18) 0.01442(16) 0.0254(6) Uani 1 1 d . . . C7B C 0.0334(3) 0.6730(2) -0.2114(2) 0.0522(9) Uani 1 1 d . . . H7BA H -0.0359 0.6462 -0.2078 0.078 Uiso 1 1 calc R . . H7BB H 0.0649 0.6891 -0.2718 0.078 Uiso 1 1 calc R . . H7BC H 0.0121 0.7328 -0.2048 0.078 Uiso 1 1 calc R . . C8B C 0.3815(2) 0.37759(17) 0.09286(16) 0.0247(5) Uani 1 1 d . . . C9B C 0.4669(2) 0.29707(18) 0.09850(16) 0.0270(6) Uani 1 1 d . . . C10B C 0.5187(2) 0.25026(19) 0.18996(16) 0.0292(6) Uani 1 1 d . . . H10A H 0.5796 0.1926 0.2168 0.035 Uiso 1 1 calc R . . C11B C 0.4972(3) 0.2636(2) 0.02473(18) 0.0355(7) Uani 1 1 d . . . C12B C 0.5257(3) 0.3472(2) -0.0648(2) 0.0552(9) Uani 1 1 d . . . H12A H 0.5928 0.3681 -0.0514 0.083 Uiso 1 1 calc R . . H12B H 0.4580 0.4029 -0.0898 0.083 Uiso 1 1 calc R . . H12C H 0.5445 0.3240 -0.1106 0.083 Uiso 1 1 calc R . . C13B C 0.3913(4) 0.2323(3) 0.0013(2) 0.0646(11) Uani 1 1 d . . . H13A H 0.4103 0.2110 -0.0457 0.097 Uiso 1 1 calc R . . H13B H 0.3239 0.2883 -0.0229 0.097 Uiso 1 1 calc R . . H13C H 0.3725 0.1778 0.0578 0.097 Uiso 1 1 calc R . . C14B C 0.6040(4) 0.1781(3) 0.0617(2) 0.0957(17) Uani 1 1 d . . . H14A H 0.6700 0.1993 0.0764 0.144 Uiso 1 1 calc R . . H14B H 0.6239 0.1574 0.0143 0.144 Uiso 1 1 calc R . . H14C H 0.5866 0.1227 0.1181 0.144 Uiso 1 1 calc R . . N1C N 0.5254(2) 0.20992(17) 0.51215(14) 0.0318(5) Uani 1 1 d . . . N2C N 0.55011(19) 0.19419(15) 0.43820(14) 0.0299(5) Uani 1 1 d . . . C1C C 0.7748(2) 0.1096(2) 0.35245(18) 0.0350(6) Uani 1 1 d . . . H1CB H 0.8060 0.1575 0.3587 0.042 Uiso 1 1 calc R . . C2C C 0.8206(3) 0.0757(2) 0.29069(19) 0.0397(7) Uani 1 1 d . . . H2CB H 0.8831 0.1006 0.2562 0.048 Uiso 1 1 calc R . . C3C C 0.7766(2) 0.0060(2) 0.27852(18) 0.0364(7) Uani 1 1 d . . . C4C C 0.6857(3) -0.0293(2) 0.33092(19) 0.0404(7) Uani 1 1 d . . . H4CA H 0.6543 -0.0769 0.3242 0.048 Uiso 1 1 calc R . . C5C C 0.6394(3) 0.00352(19) 0.39324(18) 0.0340(6) Uani 1 1 d . . . H5CA H 0.5772 -0.0218 0.4280 0.041 Uiso 1 1 calc R . . C6C C 0.6840(2) 0.07358(18) 0.40484(16) 0.0265(6) Uani 1 1 d . . . C7C C 0.8283(3) -0.0295(2) 0.2113(2) 0.0557(9) Uani 1 1 d . . . H7CA H 0.7871 -0.0777 0.2114 0.084 Uiso 1 1 calc R . . H7CB H 0.9113 -0.0604 0.2306 0.084 Uiso 1 1 calc R . . H7CC H 0.8199 0.0267 0.1484 0.084 Uiso 1 1 calc R . . C8C C 0.6342(2) 0.11088(17) 0.47082(16) 0.0242(5) Uani 1 1 d . . . C9C C 0.6648(2) 0.07153(19) 0.56778(17) 0.0295(6) Uani 1 1 d . . . C10C C 0.5922(2) 0.13850(19) 0.58977(17) 0.0323(6) Uani 1 1 d . . . H10B H 0.5901 0.1346 0.6496 0.039 Uiso 1 1 calc R . . C11C C 0.7528(3) -0.0225(2) 0.63438(18) 0.0394(7) Uani 1 1 d . . . C12C C 0.8727(3) -0.0271(3) 0.5955(2) 0.0580(9) Uani 1 1 d . . . H12D H 0.9024 0.0302 0.5862 0.087 Uiso 1 1 calc R . . H12E H 0.8652 -0.0270 0.5359 0.087 Uiso 1 1 calc R . . H12F H 0.9272 -0.0876 0.6396 0.087 Uiso 1 1 calc R . . C13C C 0.7674(4) -0.0252(3) 0.7292(2) 0.0896(15) Uani 1 1 d . . . H13D H 0.7952 0.0328 0.7203 0.134 Uiso 1 1 calc R . . H13E H 0.8242 -0.0851 0.7713 0.134 Uiso 1 1 calc R . . H13F H 0.6920 -0.0250 0.7561 0.134 Uiso 1 1 calc R . . C14C C 0.7090(3) -0.1140(2) 0.6479(3) 0.0643(10) Uani 1 1 d . . . H14D H 0.6996 -0.1120 0.5875 0.096 Uiso 1 1 calc R . . H14E H 0.6337 -0.1141 0.6750 0.096 Uiso 1 1 calc R . . H14F H 0.7659 -0.1740 0.6898 0.096 Uiso 1 1 calc R . . N1D N 0.2272(2) 0.53750(18) 0.19669(15) 0.0362(6) Uani 1 1 d . . . N2D N 0.1984(2) 0.55058(17) 0.27235(15) 0.0366(6) Uani 1 1 d . . . C1D C -0.0171(3) 0.6116(3) 0.3679(2) 0.0479(8) Uani 1 1 d . . . H1DB H -0.0344 0.5577 0.3632 0.057 Uiso 1 1 calc R . . C2D C -0.0682(3) 0.6363(3) 0.4340(2) 0.0600(10) Uani 1 1 d . . . H2DB H -0.1196 0.5986 0.4734 0.072 Uiso 1 1 calc R . . C3D C -0.0463(3) 0.7138(3) 0.4438(2) 0.0554(10) Uani 1 1 d . . . C4D C 0.0316(3) 0.7666(2) 0.3857(2) 0.0561(10) Uani 1 1 d . . . H4DA H 0.0499 0.8194 0.3917 0.067 Uiso 1 1 calc R . . C5D C 0.0832(3) 0.7432(2) 0.31887(18) 0.0413(7) Uani 1 1 d . . . H5DA H 0.1351 0.7807 0.2800 0.050 Uiso 1 1 calc R . . C6D C 0.0593(2) 0.66529(19) 0.30854(17) 0.0316(6) Uani 1 1 d . . . C7D C -0.1029(4) 0.7408(3) 0.5159(2) 0.0874(15) Uani 1 1 d . . . H7DA H -0.1541 0.6959 0.5502 0.131 Uiso 1 1 calc R . . H7DB H -0.1490 0.8087 0.4843 0.131 Uiso 1 1 calc R . . H7DC H -0.0420 0.7349 0.5595 0.131 Uiso 1 1 calc R . . C8D C 0.1145(2) 0.63507(18) 0.23947(17) 0.0289(6) Uani 1 1 d . . . C9D C 0.0882(2) 0.67647(18) 0.14228(16) 0.0275(6) Uani 1 1 d . . . C10D C 0.1623(2) 0.61109(19) 0.11928(18) 0.0335(6) Uani 1 1 d . . . H10D H 0.1665 0.6173 0.0586 0.040 Uiso 1 1 calc R . . C11D C -0.0023(2) 0.76882(19) 0.07503(17) 0.0312(6) Uani 1 1 d . . . C12D C -0.0083(3) 0.7738(2) -0.02126(19) 0.0498(8) Uani 1 1 d . . . H12J H -0.0314 0.7150 -0.0153 0.075 Uiso 1 1 calc R . . H12K H 0.0686 0.7768 -0.0457 0.075 Uiso 1 1 calc R . . H12L H -0.0658 0.8328 -0.0640 0.075 Uiso 1 1 calc R . . C13D C -0.1230(2) 0.7672(2) 0.1122(2) 0.0472(8) Uani 1 1 d . . . H13J H -0.1470 0.7079 0.1204 0.071 Uiso 1 1 calc R . . H13K H -0.1797 0.8259 0.0679 0.071 Uiso 1 1 calc R . . H13L H -0.1197 0.7667 0.1723 0.071 Uiso 1 1 calc R . . C14D C 0.0346(3) 0.8626(2) 0.0628(2) 0.0484(8) Uani 1 1 d . . . H14J H 0.0393 0.8611 0.1233 0.073 Uiso 1 1 calc R . . H14K H -0.0233 0.9211 0.0197 0.073 Uiso 1 1 calc R . . H14L H 0.1111 0.8650 0.0377 0.073 Uiso 1 1 calc R . . H1C H 0.471(3) 0.262(2) 0.509(2) 0.052(9) Uiso 1 1 d . . . H1B H 0.480(4) 0.283(3) 0.302(3) 0.097(13) Uiso 1 1 d . . . H1A H 0.289(4) 0.480(3) 0.404(3) 0.095(14) Uiso 1 1 d . . . H1D H 0.283(4) 0.481(3) 0.198(3) 0.098(14) Uiso 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 N1A 0.0410(14) 0.0295(12) 0.0208(11) -0.0105(10) -0.0015(10) 0.0017(11) N2A 0.0343(13) 0.0284(12) 0.0214(11) -0.0107(10) 0.0014(9) -0.0010(10) C1A 0.0379(16) 0.0297(15) 0.0298(14) -0.0156(12) 0.0049(12) -0.0063(12) C2A 0.058(2) 0.0282(15) 0.0252(14) -0.0112(12) 0.0098(14) -0.0137(14) C3A 0.0521(19) 0.0276(15) 0.0203(13) -0.0139(12) 0.0013(12) 0.0016(13) C4A 0.0356(16) 0.0371(16) 0.0329(15) -0.0170(14) 0.0019(13) -0.0017(13) C5A 0.0344(15) 0.0294(15) 0.0290(14) -0.0120(12) 0.0051(12) -0.0077(12) C6A 0.0322(15) 0.0232(13) 0.0225(12) -0.0120(11) 0.0039(11) -0.0041(11) C7A 0.070(2) 0.0360(17) 0.0287(15) -0.0102(13) -0.0073(15) 0.0058(16) C8A 0.0284(14) 0.0289(14) 0.0216(12) -0.0136(11) 0.0062(11) -0.0065(11) C9A 0.0307(14) 0.0228(13) 0.0237(12) -0.0100(11) 0.0036(11) -0.0044(11) C10A 0.0384(16) 0.0273(14) 0.0245(13) -0.0091(12) 0.0005(12) 0.0008(12) C11A 0.0360(15) 0.0256(14) 0.0249(13) -0.0126(11) -0.0001(11) -0.0024(12) C12A 0.0467(18) 0.0464(18) 0.0327(15) -0.0240(14) 0.0110(13) -0.0151(15) C13A 0.0445(17) 0.0328(15) 0.0353(15) -0.0187(13) 0.0066(13) -0.0094(13) C14A 0.054(2) 0.0389(17) 0.0429(17) -0.0263(15) -0.0019(15) 0.0059(15) N1B 0.0356(13) 0.0274(12) 0.0224(11) -0.0109(10) -0.0026(10) -0.0007(10) N2B 0.0323(12) 0.0283(12) 0.0228(11) -0.0121(10) 0.0011(9) -0.0021(10) C1B 0.0326(15) 0.0263(14) 0.0311(14) -0.0124(12) -0.0004(12) -0.0067(12) C2B 0.0423(17) 0.0274(15) 0.0294(14) -0.0110(12) 0.0017(13) -0.0013(13) C3B 0.0354(16) 0.0389(16) 0.0226(13) -0.0142(13) 0.0000(12) 0.0064(13) C4B 0.0230(14) 0.0522(19) 0.0352(15) -0.0187(15) -0.0018(12) -0.0030(13) C5B 0.0321(15) 0.0345(16) 0.0281(14) -0.0098(12) 0.0020(12) -0.0066(13) C6B 0.0272(14) 0.0291(14) 0.0211(12) -0.0150(11) 0.0032(10) -0.0010(11) C7B 0.0462(19) 0.061(2) 0.0330(16) -0.0171(16) -0.0059(14) 0.0091(16) C8B 0.0292(14) 0.0247(13) 0.0214(12) -0.0120(11) 0.0020(10) -0.0059(11) C9B 0.0342(15) 0.0242(13) 0.0210(12) -0.0107(11) -0.0036(11) -0.0026(11) C10B 0.0331(15) 0.0259(14) 0.0255(13) -0.0122(11) -0.0046(11) 0.0004(12) C11B 0.0431(17) 0.0339(15) 0.0294(14) -0.0191(13) -0.0043(12) 0.0029(13) C12B 0.074(2) 0.068(2) 0.0350(17) -0.0336(17) 0.0124(16) -0.0166(19) C13B 0.095(3) 0.076(3) 0.057(2) -0.052(2) 0.019(2) -0.039(2) C14B 0.121(4) 0.096(3) 0.053(2) -0.057(2) -0.036(2) 0.071(3) N1C 0.0392(14) 0.0310(13) 0.0269(12) -0.0178(11) 0.0054(10) -0.0016(11) N2C 0.0372(13) 0.0290(12) 0.0257(11) -0.0165(10) 0.0024(10) -0.0030(10) C1C 0.0323(15) 0.0439(17) 0.0324(14) -0.0215(13) 0.0022(12) -0.0076(13) C2C 0.0316(16) 0.0532(19) 0.0305(14) -0.0201(14) 0.0029(12) -0.0009(14) C3C 0.0358(16) 0.0365(16) 0.0323(15) -0.0202(13) -0.0053(13) 0.0120(13) C4C 0.055(2) 0.0332(16) 0.0373(16) -0.0237(14) -0.0031(14) -0.0013(14) C5C 0.0409(16) 0.0317(15) 0.0301(14) -0.0157(12) 0.0016(12) -0.0065(13) C6C 0.0280(14) 0.0267(14) 0.0212(12) -0.0122(11) -0.0036(11) 0.0035(11) C7C 0.061(2) 0.061(2) 0.0400(17) -0.0320(17) -0.0059(16) 0.0202(18) C8C 0.0287(14) 0.0217(13) 0.0205(12) -0.0092(11) -0.0007(10) -0.0038(11) C9C 0.0329(15) 0.0292(14) 0.0238(13) -0.0125(12) 0.0023(11) -0.0017(12) C10C 0.0422(16) 0.0308(15) 0.0209(13) -0.0113(12) 0.0044(12) -0.0046(13) C11C 0.0466(18) 0.0374(16) 0.0241(14) -0.0122(13) -0.0092(13) 0.0058(14) C12C 0.044(2) 0.063(2) 0.055(2) -0.0245(18) -0.0100(16) 0.0051(17) C13C 0.126(4) 0.080(3) 0.0340(18) -0.0295(19) -0.037(2) 0.047(3) C14C 0.064(2) 0.0312(18) 0.067(2) -0.0038(17) -0.0068(19) 0.0014(17) N1D 0.0379(14) 0.0386(14) 0.0291(12) -0.0192(11) 0.0005(10) 0.0058(11) N2D 0.0391(14) 0.0387(13) 0.0273(12) -0.0177(11) 0.0005(10) 0.0065(11) C1D 0.0409(18) 0.070(2) 0.0407(17) -0.0310(17) 0.0075(14) -0.0187(17) C2D 0.0372(19) 0.098(3) 0.0448(19) -0.037(2) 0.0125(15) -0.0096(19) C3D 0.052(2) 0.065(2) 0.0297(16) -0.0215(17) -0.0039(15) 0.0242(18) C4D 0.084(3) 0.0367(18) 0.0380(17) -0.0210(15) -0.0081(18) 0.0157(18) C5D 0.058(2) 0.0326(16) 0.0276(14) -0.0132(13) 0.0062(14) -0.0010(14) C6D 0.0305(15) 0.0352(15) 0.0217(13) -0.0117(12) -0.0026(11) 0.0034(12) C7D 0.086(3) 0.113(3) 0.046(2) -0.048(2) -0.002(2) 0.038(3) C8D 0.0287(14) 0.0271(14) 0.0253(13) -0.0103(11) -0.0017(11) -0.0002(11) C9D 0.0296(14) 0.0290(14) 0.0239(13) -0.0131(12) -0.0011(11) -0.0046(12) C10D 0.0385(16) 0.0324(15) 0.0258(13) -0.0126(12) 0.0002(12) -0.0030(13) C11D 0.0347(15) 0.0268(14) 0.0268(13) -0.0094(12) -0.0019(12) -0.0043(12) C12D 0.066(2) 0.0434(18) 0.0303(15) -0.0148(14) -0.0146(15) 0.0029(16) C13D 0.0328(17) 0.0472(19) 0.0436(17) -0.0107(15) -0.0071(14) 0.0013(15) C14D 0.066(2) 0.0275(15) 0.0430(17) -0.0098(14) -0.0083(16) -0.0085(15) _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 N1A C10A 1.354(3) . ? N1A N2A 1.362(3) . ? N2A C8A 1.362(3) . ? C1A C2A 1.402(4) . ? C1A C6A 1.408(3) . ? C2A C3A 1.392(4) . ? C3A C4A 1.398(4) . ? C3A C7A 1.522(4) . ? C4A C5A 1.404(4) . ? C5A C6A 1.389(4) . ? C6A C8A 1.499(3) . ? C8A C9A 1.421(3) . ? C9A C10A 1.390(3) . ? C9A C11A 1.536(3) . ? C11A C13A 1.534(4) . ? C11A C14A 1.547(4) . ? C11A C12A 1.548(4) . ? N1B C10B 1.348(3) . ? N1B N2B 1.363(3) . ? N2B C8B 1.366(3) . ? C1B C2B 1.394(4) . ? C1B C6B 1.410(3) . ? C2B C3B 1.396(4) . ? C3B C4B 1.401(4) . ? C3B C7B 1.515(4) . ? C4B C5B 1.399(4) . ? C5B C6B 1.395(4) . ? C6B C8B 1.499(3) . ? C8B C9B 1.414(3) . ? C9B C10B 1.402(3) . ? C9B C11B 1.537(3) . ? C11B C14B 1.525(4) . ? C11B C12B 1.526(4) . ? C11B C13B 1.545(4) . ? N1C C10C 1.352(3) . ? N1C N2C 1.358(3) . ? N2C C8C 1.348(3) . ? C1C C6C 1.394(4) . ? C1C C2C 1.400(3) . ? C2C C3C 1.398(4) . ? C3C C4C 1.392(4) . ? C3C C7C 1.518(3) . ? C4C C5C 1.399(3) . ? C5C C6C 1.403(4) . ? C6C C8C 1.510(3) . ? C8C C9C 1.426(3) . ? C9C C10C 1.395(3) . ? C9C C11C 1.533(4) . ? C11C C12C 1.534(4) . ? C11C C13C 1.542(4) . ? C11C C14C 1.548(4) . ? N1D C10D 1.351(3) . ? N1D N2D 1.371(3) . ? N2D C8D 1.358(3) . ? C1D C2D 1.397(4) . ? C1D C6D 1.401(4) . ? C2D C3D 1.378(5) . ? C3D C4D 1.401(5) . ? C3D C7D 1.527(4) . ? C4D C5D 1.397(4) . ? C5D C6D 1.398(4) . ? C6D C8D 1.507(3) . ? C8D C9D 1.417(3) . ? C9D C10D 1.395(4) . ? C9D C11D 1.538(3) . ? C11D C13D 1.531(4) . ? C11D C12D 1.541(4) . ? C11D C14D 1.547(4) . ? 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 C10A N1A N2A 110.3(2) . . ? C8A N2A N1A 106.1(2) . . ? C2A C1A C6A 120.2(3) . . ? C3A C2A C1A 122.1(3) . . ? C2A C3A C4A 117.2(3) . . ? C2A C3A C7A 121.7(3) . . ? C4A C3A C7A 121.1(3) . . ? C3A C4A C5A 121.3(3) . . ? C6A C5A C4A 121.2(2) . . ? C5A C6A C1A 117.9(2) . . ? C5A C6A C8A 122.2(2) . . ? C1A C6A C8A 119.9(2) . . ? N2A C8A C9A 110.6(2) . . ? N2A C8A C6A 117.9(2) . . ? C9A C8A C6A 131.4(2) . . ? C10A C9A C8A 103.6(2) . . ? C10A C9A C11A 126.6(2) . . ? C8A C9A C11A 129.7(2) . . ? N1A C10A C9A 109.4(2) . . ? C9A C11A C13A 111.9(2) . . ? C9A C11A C14A 109.7(2) . . ? C13A C11A C14A 108.2(2) . . ? C9A C11A C12A 109.1(2) . . ? C13A C11A C12A 109.4(2) . . ? C14A C11A C12A 108.5(2) . . ? C10B N1B N2B 110.6(2) . . ? N1B N2B C8B 106.18(19) . . ? C2B C1B C6B 120.5(3) . . ? C1B C2B C3B 122.0(3) . . ? C2B C3B C4B 117.3(3) . . ? C2B C3B C7B 122.2(3) . . ? C4B C3B C7B 120.5(3) . . ? C5B C4B C3B 121.1(3) . . ? C6B C5B C4B 121.4(3) . . ? C5B C6B C1B 117.6(2) . . ? C5B C6B C8B 120.5(2) . . ? C1B C6B C8B 121.9(2) . . ? N2B C8B C9B 110.3(2) . . ? N2B C8B C6B 119.3(2) . . ? C9B C8B C6B 130.4(2) . . ? C10B C9B C8B 104.1(2) . . ? C10B C9B C11B 126.2(2) . . ? C8B C9B C11B 129.7(2) . . ? N1B C10B C9B 108.8(2) . . ? C14B C11B C12B 108.1(3) . . ? C14B C11B C9B 109.5(2) . . ? C12B C11B C9B 111.1(2) . . ? C14B C11B C13B 110.7(3) . . ? C12B C11B C13B 108.2(2) . . ? C9B C11B C13B 109.3(2) . . ? C10C N1C N2C 110.8(2) . . ? C8C N2C N1C 105.9(2) . . ? C6C C1C C2C 120.5(3) . . ? C3C C2C C1C 121.7(3) . . ? C4C C3C C2C 117.4(2) . . ? C4C C3C C7C 122.2(3) . . ? C2C C3C C7C 120.4(3) . . ? C3C C4C C5C 121.6(3) . . ? C4C C5C C6C 120.5(3) . . ? C1C C6C C5C 118.2(2) . . ? C1C C6C C8C 120.4(2) . . ? C5C C6C C8C 121.3(2) . . ? N2C C8C C9C 111.2(2) . . ? N2C C8C C6C 119.5(2) . . ? C9C C8C C6C 129.3(2) . . ? C10C C9C C8C 103.1(2) . . ? C10C C9C C11C 127.2(2) . . ? C8C C9C C11C 129.7(2) . . ? N1C C10C C9C 108.9(2) . . ? C9C C11C C12C 111.3(2) . . ? C9C C11C C13C 109.8(2) . . ? C12C C11C C13C 108.5(3) . . ? C9C C11C C14C 109.6(2) . . ? C12C C11C C14C 107.9(3) . . ? C13C C11C C14C 109.7(3) . . ? C10D N1D N2D 110.2(2) . . ? C8D N2D N1D 105.9(2) . . ? C2D C1D C6D 120.9(3) . . ? C3D C2D C1D 122.0(3) . . ? C2D C3D C4D 117.3(3) . . ? C2D C3D C7D 121.8(4) . . ? C4D C3D C7D 121.0(4) . . ? C5D C4D C3D 121.5(3) . . ? C4D C5D C6D 120.8(3) . . ? C5D C6D C1D 117.5(2) . . ? C5D C6D C8D 123.2(2) . . ? C1D C6D C8D 119.3(2) . . ? N2D C8D C9D 110.9(2) . . ? N2D C8D C6D 118.1(2) . . ? C9D C8D C6D 130.7(2) . . ? C10D C9D C8D 103.6(2) . . ? C10D C9D C11D 126.1(2) . . ? C8D C9D C11D 130.2(2) . . ? N1D C10D C9D 109.4(2) . . ? C13D C11D C9D 110.7(2) . . ? C13D C11D C12D 109.6(2) . . ? C9D C11D C12D 109.7(2) . . ? C13D C11D C14D 108.9(2) . . ? C9D C11D C14D 109.9(2) . . ? C12D C11D C14D 107.9(2) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.325 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.066 #===END data_trof61 _database_code_CSD 163026 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H22 N2' _chemical_formula_weight 194.32 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 Tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 18.9969(10) _cell_length_b 18.9969(10) _cell_length_c 13.3498(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4817.7(11) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.072 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9720 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11104 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.35 _reflns_number_total 2810 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0422P)^2^+5.7782P] 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 2810 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1141 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1388 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 N1 N 0.48859(9) 0.65946(9) 0.02207(13) 0.0255(4) Uani 1 1 d . . . N2 N 0.42333(9) 0.66831(9) 0.05988(12) 0.0300(4) Uani 1 1 d . . . H0 H 0.5272(14) 0.6632(13) 0.0661(19) 0.052(7) Uiso 1 1 d . . . C1 C 0.38155(11) 0.66307(11) -0.01946(16) 0.0283(5) Uani 1 1 d . . . H1A H 0.3314(12) 0.6686(11) -0.0113(16) 0.032(6) Uiso 1 1 d . . . C2 C 0.41848(10) 0.65087(9) -0.10882(14) 0.0223(4) Uani 1 1 d . . . C3 C 0.48905(10) 0.64865(9) -0.07853(14) 0.0210(4) Uani 1 1 d . . . C4 C 0.38253(10) 0.64178(10) -0.20997(15) 0.0268(5) Uani 1 1 d . . . C5 C 0.34952(14) 0.56807(12) -0.2160(2) 0.0389(6) Uani 1 1 d . . . H5B H 0.3129(14) 0.5619(13) -0.160(2) 0.055(8) Uiso 1 1 d . . . H5A H 0.3857(14) 0.5297(14) -0.2087(18) 0.054(7) Uiso 1 1 d . . . H5C H 0.3268(12) 0.5616(12) -0.2826(18) 0.042(6) Uiso 1 1 d . . . C6 C 0.43265(14) 0.65192(16) -0.29827(17) 0.0420(6) Uani 1 1 d . . . H6A H 0.4578(14) 0.7005(15) -0.296(2) 0.063(8) Uiso 1 1 d . . . H6B H 0.4700(13) 0.6145(13) -0.3011(18) 0.046(7) Uiso 1 1 d . . . H6C H 0.4062(12) 0.6492(12) -0.3630(19) 0.045(7) Uiso 1 1 d . . . C7 C 0.32313(13) 0.69621(13) -0.2204(2) 0.0392(6) Uani 1 1 d . . . H7A H 0.2876(14) 0.6896(13) -0.167(2) 0.056(8) Uiso 1 1 d . . . H7B H 0.3420(12) 0.7451(14) -0.2192(18) 0.047(7) Uiso 1 1 d . . . H7C H 0.2985(13) 0.6906(13) -0.288(2) 0.054(7) Uiso 1 1 d . . . C8 C 0.55922(10) 0.64031(10) -0.12855(16) 0.0239(4) Uani 1 1 d . . . H8A H 0.5932(11) 0.6736(11) -0.0952(15) 0.028(5) Uiso 1 1 d . . . H8B H 0.5568(11) 0.6559(11) -0.1983(17) 0.030(6) Uiso 1 1 d . . . C9 C 0.59400(10) 0.56634(10) -0.12619(15) 0.0260(5) Uani 1 1 d . . . C10 C 0.66696(12) 0.57294(15) -0.1743(2) 0.0399(6) Uani 1 1 d . . . H10A H 0.6917(13) 0.5269(13) -0.1741(18) 0.047(7) Uiso 1 1 d . . . H10C H 0.6623(13) 0.5907(13) -0.246(2) 0.053(8) Uiso 1 1 d . . . H10B H 0.6976(13) 0.6062(13) -0.1319(18) 0.048(7) Uiso 1 1 d . . . C11 C 0.55053(12) 0.51281(12) -0.18489(18) 0.0329(5) Uani 1 1 d . . . H11A H 0.5707(12) 0.4637(13) -0.1792(17) 0.048(7) Uiso 1 1 d . . . H11C H 0.5025(13) 0.5105(11) -0.1601(16) 0.039(6) Uiso 1 1 d . . . H11B H 0.5469(12) 0.5264(12) -0.2594(19) 0.044(7) Uiso 1 1 d . . . C12 C 0.60273(13) 0.54035(13) -0.01873(17) 0.0332(5) Uani 1 1 d . . . H12C H 0.6285(12) 0.5744(12) 0.0211(17) 0.036(6) Uiso 1 1 d . . . H12B H 0.6296(12) 0.4951(13) -0.0164(17) 0.045(7) Uiso 1 1 d . . . H12A H 0.5561(13) 0.5323(12) 0.0147(18) 0.048(7) Uiso 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 N1 0.0242(9) 0.0299(9) 0.0223(9) -0.0048(7) -0.0018(7) 0.0014(7) N2 0.0293(9) 0.0362(10) 0.0246(9) -0.0080(8) 0.0036(8) 0.0036(8) C1 0.0227(10) 0.0318(11) 0.0304(11) -0.0054(9) 0.0027(9) 0.0018(9) C2 0.0227(10) 0.0201(9) 0.0240(10) -0.0017(8) -0.0010(8) 0.0005(8) C3 0.0236(10) 0.0191(9) 0.0202(9) -0.0010(8) -0.0008(8) -0.0006(8) C4 0.0256(10) 0.0294(10) 0.0254(10) -0.0021(9) -0.0061(8) 0.0023(9) C5 0.0407(14) 0.0325(12) 0.0435(14) -0.0080(11) -0.0192(12) 0.0001(11) C6 0.0384(13) 0.0647(18) 0.0229(12) 0.0034(12) -0.0059(10) 0.0025(13) C7 0.0358(13) 0.0346(13) 0.0472(15) -0.0022(12) -0.0157(12) 0.0064(11) C8 0.0229(10) 0.0250(10) 0.0238(10) 0.0021(9) 0.0010(8) -0.0041(8) C9 0.0217(10) 0.0282(10) 0.0281(11) 0.0012(9) 0.0023(8) 0.0013(8) C10 0.0252(11) 0.0481(15) 0.0464(15) 0.0019(13) 0.0077(11) 0.0050(11) C11 0.0322(12) 0.0300(12) 0.0366(13) -0.0045(10) 0.0005(10) 0.0020(10) C12 0.0349(12) 0.0324(12) 0.0321(12) 0.0060(10) -0.0039(11) 0.0035(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 N1 N2 1.349(2) . ? N1 C3 1.359(2) . ? N2 C1 1.327(3) . ? C1 C2 1.403(3) . ? C2 C3 1.401(3) . ? C2 C4 1.523(3) . ? C3 C8 1.499(3) . ? C4 C6 1.527(3) . ? C4 C5 1.536(3) . ? C4 C7 1.537(3) . ? C8 C9 1.553(3) . ? C9 C12 1.526(3) . ? C9 C11 1.527(3) . ? C9 C10 1.533(3) . ? 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 N2 N1 C3 113.24(16) . . ? C1 N2 N1 103.99(16) . . ? N2 C1 C2 113.07(18) . . ? C3 C2 C1 103.77(16) . . ? C3 C2 C4 132.97(17) . . ? C1 C2 C4 123.25(17) . . ? N1 C3 C2 105.94(16) . . ? N1 C3 C8 117.52(17) . . ? C2 C3 C8 136.50(18) . . ? C2 C4 C6 112.98(17) . . ? C2 C4 C5 109.42(17) . . ? C6 C4 C5 109.2(2) . . ? C2 C4 C7 109.45(17) . . ? C6 C4 C7 107.6(2) . . ? C5 C4 C7 107.99(18) . . ? C3 C8 C9 117.70(16) . . ? C12 C9 C11 109.02(18) . . ? C12 C9 C10 108.80(19) . . ? C11 C9 C10 109.17(18) . . ? C12 C9 C8 110.98(17) . . ? C11 C9 C8 111.23(17) . . ? C10 C9 C8 107.58(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H0 N2 0.94(3) 1.96(3) 2.869(2) 161(2) 12_766 _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.188 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.047 #===END data_trof74 _database_code_CSD 163027 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N2' _chemical_formula_weight 166.26 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 C2/c 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' '-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 12.7395(4) _cell_length_b 28.0431(7) _cell_length_c 12.2071(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.0824(19) _cell_angle_gamma 90.00 _cell_volume 4317.7(3) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.023 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9878 _exptl_absorpt_correction_T_max 0.9939 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7192 _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 23.50 _reflns_number_total 2893 _reflns_number_gt 2013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0299P)^2^+7.6535P] 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 SHELXL _refine_ls_extinction_coef 0.0021(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2893 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _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 N1A N 0.0401(2) 0.28243(10) 0.0925(2) 0.0389(8) Uani 1 1 d . . . N2A N 0.1178(2) 0.26943(10) 0.1737(3) 0.0357(8) Uani 1 1 d . . . H2A H 0.147(3) 0.2902(14) 0.229(3) 0.064(13) Uiso 1 1 d . . . C1A C 0.1528(3) 0.22412(11) 0.1626(3) 0.0293(8) Uani 1 1 d . . . C2A C 0.0935(3) 0.20635(11) 0.0671(3) 0.0301(8) Uani 1 1 d . . . C3A C 0.0256(3) 0.24379(12) 0.0292(3) 0.0368(9) Uani 1 1 d . . . H3AA H -0.0257 0.2418 -0.0352 0.044 Uiso 1 1 calc R . . C4A C 0.2396(3) 0.20375(12) 0.2448(3) 0.0346(9) Uani 1 1 d . . . H4AA H 0.2457 0.1691 0.2279 0.041 Uiso 1 1 calc R . . C5A C 0.2155(3) 0.20799(15) 0.3630(3) 0.0574(12) Uani 1 1 d . . . H5AA H 0.1475 0.1926 0.3689 0.086 Uiso 1 1 calc R . . H5AB H 0.2117 0.2417 0.3829 0.086 Uiso 1 1 calc R . . H5AC H 0.2717 0.1924 0.4135 0.086 Uiso 1 1 calc R . . C6A C 0.3459(3) 0.22713(16) 0.2338(4) 0.0600(12) Uani 1 1 d . . . H6AA H 0.3608 0.2236 0.1576 0.090 Uiso 1 1 calc R . . H6AB H 0.4022 0.2117 0.2845 0.090 Uiso 1 1 calc R . . H6AC H 0.3429 0.2611 0.2522 0.090 Uiso 1 1 calc R . . C7A C 0.0994(3) 0.15707(12) 0.0153(3) 0.0380(9) Uani 1 1 d . . . C8A C 0.2120(3) 0.14675(14) -0.0085(3) 0.0519(11) Uani 1 1 d . . . H8AA H 0.2143 0.1150 -0.0417 0.078 Uiso 1 1 calc R . . H8AB H 0.2612 0.1479 0.0608 0.078 Uiso 1 1 calc R . . H8AC H 0.2326 0.1708 -0.0597 0.078 Uiso 1 1 calc R . . C9A C 0.0258(4) 0.15576(14) -0.0946(3) 0.0594(12) Uani 1 1 d . . . H9AA H -0.0472 0.1618 -0.0816 0.089 Uiso 1 1 calc R . . H9AB H 0.0298 0.1243 -0.1288 0.089 Uiso 1 1 calc R . . H9AC H 0.0474 0.1803 -0.1441 0.089 Uiso 1 1 calc R . . C10A C 0.0647(3) 0.11877(13) 0.0923(3) 0.0546(11) Uani 1 1 d . . . H10A H -0.0078 0.1255 0.1063 0.082 Uiso 1 1 calc R . . H10B H 0.1126 0.1190 0.1625 0.082 Uiso 1 1 calc R . . H10C H 0.0669 0.0874 0.0573 0.082 Uiso 1 1 calc R . . N1B N 0.1888(2) 0.34355(10) 0.3235(2) 0.0396(8) Uani 1 1 d . . . N2B N 0.1130(2) 0.35756(10) 0.3851(2) 0.0365(8) Uani 1 1 d . . . H2B H 0.059(3) 0.3362(14) 0.394(3) 0.066(13) Uiso 1 1 d . . . C1B C 0.1266(3) 0.40302(11) 0.4208(3) 0.0320(9) Uani 1 1 d . . . C2B C 0.2163(3) 0.42025(11) 0.3814(3) 0.0343(9) Uani 1 1 d . . . C3B C 0.2499(3) 0.38174(12) 0.3222(3) 0.0381(9) Uani 1 1 d . . . H3BA H 0.3105 0.3829 0.2848 0.046 Uiso 1 1 calc R . . C4B C 0.0472(3) 0.42398(12) 0.4869(3) 0.0386(10) Uani 1 1 d . . . H4BA H 0.0698 0.4574 0.5069 0.046 Uiso 1 1 calc R . . C5B C -0.0607(3) 0.42620(16) 0.4172(3) 0.0580(12) Uani 1 1 d . . . H5BA H -0.0549 0.4426 0.3474 0.087 Uiso 1 1 calc R . . H5BB H -0.1099 0.4437 0.4575 0.087 Uiso 1 1 calc R . . H5BC H -0.0873 0.3938 0.4016 0.087 Uiso 1 1 calc R . . C6B C 0.0416(4) 0.39687(16) 0.5935(3) 0.0698(14) Uani 1 1 d . . . H6BA H 0.1120 0.3961 0.6377 0.105 Uiso 1 1 calc R . . H6BB H 0.0177 0.3642 0.5761 0.105 Uiso 1 1 calc R . . H6BC H -0.0084 0.4128 0.6355 0.105 Uiso 1 1 calc R . . C7B C 0.2675(3) 0.46896(12) 0.3965(3) 0.0399(10) Uani 1 1 d . . . C8B C 0.1901(3) 0.50760(13) 0.3456(3) 0.0513(11) Uani 1 1 d . . . H8BA H 0.1686 0.5008 0.2669 0.077 Uiso 1 1 calc R . . H8BB H 0.2249 0.5388 0.3538 0.077 Uiso 1 1 calc R . . H8BC H 0.1273 0.5078 0.3837 0.077 Uiso 1 1 calc R . . C9B C 0.3011(3) 0.47968(14) 0.5199(3) 0.0542(12) Uani 1 1 d . . . H9BA H 0.3502 0.4549 0.5525 0.081 Uiso 1 1 calc R . . H9BB H 0.2383 0.4801 0.5579 0.081 Uiso 1 1 calc R . . H9BC H 0.3363 0.5108 0.5280 0.081 Uiso 1 1 calc R . . C10B C 0.3663(3) 0.47103(14) 0.3381(4) 0.0609(13) Uani 1 1 d . . . H10D H 0.3466 0.4637 0.2594 0.091 Uiso 1 1 calc R . . H10E H 0.4184 0.4476 0.3715 0.091 Uiso 1 1 calc R . . H10F H 0.3973 0.5031 0.3461 0.091 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 N1A 0.043(2) 0.0341(18) 0.0387(18) 0.0000(14) 0.0033(16) 0.0052(15) N2A 0.040(2) 0.0287(17) 0.0376(19) -0.0073(14) 0.0042(16) 0.0000(14) C1A 0.030(2) 0.0266(19) 0.032(2) -0.0005(15) 0.0080(17) 0.0010(15) C2A 0.027(2) 0.033(2) 0.030(2) 0.0002(16) 0.0036(16) -0.0009(16) C3A 0.035(2) 0.038(2) 0.036(2) -0.0048(17) 0.0009(18) 0.0004(17) C4A 0.037(2) 0.036(2) 0.0296(19) -0.0028(16) 0.0023(17) 0.0025(17) C5A 0.064(3) 0.071(3) 0.038(2) 0.005(2) 0.008(2) 0.010(2) C6A 0.042(3) 0.079(3) 0.057(3) 0.009(2) 0.001(2) -0.003(2) C7A 0.044(3) 0.0285(19) 0.042(2) -0.0051(16) 0.0056(19) -0.0007(16) C8A 0.055(3) 0.050(3) 0.054(3) -0.018(2) 0.018(2) 0.008(2) C9A 0.071(3) 0.049(3) 0.055(3) -0.020(2) -0.004(2) -0.007(2) C10A 0.069(3) 0.030(2) 0.067(3) -0.0046(19) 0.018(2) -0.004(2) N1B 0.043(2) 0.0338(17) 0.0431(19) -0.0089(14) 0.0088(16) 0.0021(15) N2B 0.037(2) 0.0295(17) 0.0441(19) -0.0031(14) 0.0086(16) -0.0005(14) C1B 0.042(2) 0.0230(18) 0.030(2) -0.0029(14) 0.0041(17) -0.0002(16) C2B 0.039(2) 0.0259(19) 0.038(2) -0.0048(16) 0.0087(18) 0.0006(16) C3B 0.038(2) 0.034(2) 0.044(2) -0.0053(17) 0.0106(19) -0.0013(17) C4B 0.040(3) 0.035(2) 0.042(2) -0.0069(17) 0.013(2) 0.0014(17) C5B 0.043(3) 0.069(3) 0.064(3) -0.011(2) 0.014(2) 0.011(2) C6B 0.102(4) 0.070(3) 0.045(3) 0.006(2) 0.035(3) 0.023(3) C7B 0.043(2) 0.030(2) 0.048(2) -0.0050(17) 0.010(2) -0.0021(17) C8B 0.064(3) 0.033(2) 0.058(3) -0.0049(19) 0.013(2) -0.004(2) C9B 0.058(3) 0.042(2) 0.059(3) -0.012(2) -0.001(2) -0.009(2) C10B 0.056(3) 0.043(2) 0.089(3) -0.006(2) 0.029(3) -0.016(2) _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 N1A C3A 1.328(4) . ? N1A N2A 1.350(4) . ? N2A C1A 1.360(4) . ? C1A C2A 1.390(5) . ? C1A C4A 1.498(5) . ? C2A C3A 1.398(5) . ? C2A C7A 1.526(4) . ? C4A C5A 1.522(5) . ? C4A C6A 1.527(5) . ? C7A C9A 1.526(5) . ? C7A C8A 1.530(5) . ? C7A C10A 1.533(5) . ? N1B C3B 1.326(4) . ? N1B N2B 1.364(4) . ? N2B C1B 1.351(4) . ? C1B C2B 1.387(4) . ? C1B C4B 1.500(4) . ? C2B C3B 1.400(4) . ? C2B C7B 1.514(5) . ? C4B C5B 1.513(5) . ? C4B C6B 1.518(5) . ? C7B C10B 1.532(5) . ? C7B C8B 1.537(5) . ? C7B C9B 1.537(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 C3A N1A N2A 103.6(3) . . ? N1A N2A C1A 113.3(3) . . ? N2A C1A C2A 105.8(3) . . ? N2A C1A C4A 120.8(3) . . ? C2A C1A C4A 133.5(3) . . ? C1A C2A C3A 104.3(3) . . ? C1A C2A C7A 128.3(3) . . ? C3A C2A C7A 127.4(3) . . ? N1A C3A C2A 113.0(3) . . ? C1A C4A C5A 112.1(3) . . ? C1A C4A C6A 110.9(3) . . ? C5A C4A C6A 110.5(3) . . ? C2A C7A C9A 109.0(3) . . ? C2A C7A C8A 110.6(3) . . ? C9A C7A C8A 107.8(3) . . ? C2A C7A C10A 110.2(3) . . ? C9A C7A C10A 109.1(3) . . ? C8A C7A C10A 110.1(3) . . ? C3B N1B N2B 103.7(3) . . ? C1B N2B N1B 112.4(3) . . ? N2B C1B C2B 107.0(3) . . ? N2B C1B C4B 118.5(3) . . ? C2B C1B C4B 134.5(3) . . ? C1B C2B C3B 103.7(3) . . ? C1B C2B C7B 129.4(3) . . ? C3B C2B C7B 126.9(3) . . ? N1B C3B C2B 113.2(3) . . ? C1B C4B C5B 110.0(3) . . ? C1B C4B C6B 112.4(3) . . ? C5B C4B C6B 110.7(3) . . ? C2B C7B C10B 110.2(3) . . ? C2B C7B C8B 110.3(3) . . ? C10B C7B C8B 108.0(3) . . ? C2B C7B C9B 110.6(3) . . ? C10B C7B C9B 108.3(3) . . ? C8B C7B C9B 109.4(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2A H2A N1B 0.93(4) 1.92(4) 2.831(4) 167(4) . N2B H2B N1A 0.93(4) 1.99(4) 2.909(4) 171(4) 2 _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 23.50 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 0.164 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.042 #===END