data_ntm _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 214.31 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.866(2) _cell_length_b 11.297(3) _cell_length_c 11.831(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1185.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 133(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 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9789 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 'BRUKER SMART' _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 15768 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.59 _reflns_number_total 2734 _reflns_number_gt 2576 _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^)+(0.0580P)^2^+0.1570P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 2734 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 -0.39420(13) 0.46372(10) 0.60811(10) 0.0209(2) Uani 1 1 d . . . C2 C -0.27500(13) 0.41859(10) 0.54363(10) 0.0199(2) Uani 1 1 d . . . H2A H -0.2899 0.3485 0.5006 0.024 Uiso 1 1 calc R . . C3 C -0.13628(13) 0.47380(10) 0.54125(9) 0.0193(2) Uani 1 1 d . . . C4 C -0.11122(12) 0.57940(9) 0.60371(9) 0.0177(2) Uani 1 1 d . . . C5 C -0.23426(12) 0.62571(9) 0.66492(10) 0.0199(2) Uani 1 1 d . . . H5A H -0.2224 0.6979 0.7051 0.024 Uiso 1 1 calc R . . C6 C -0.37144(13) 0.56835(10) 0.66764(10) 0.0212(2) Uani 1 1 d . . . H6A H -0.4517 0.6008 0.7109 0.025 Uiso 1 1 calc R . . N7 N 0.03037(11) 0.62891(8) 0.60330(8) 0.0194(2) Uani 1 1 d . . . C8 C 0.12949(13) 0.61310(10) 0.50419(10) 0.0232(2) Uani 1 1 d . . . H8A H 0.2263 0.5783 0.5295 0.028 Uiso 1 1 calc R . . H8B H 0.1515 0.6917 0.4710 0.028 Uiso 1 1 calc R . . C9 C 0.06214(14) 0.53458(11) 0.41376(10) 0.0244(2) Uani 1 1 d . . . H9A H 0.1417 0.5086 0.3605 0.029 Uiso 1 1 calc R . . H9B H -0.0153 0.5787 0.3707 0.029 Uiso 1 1 calc R . . C10 C -0.00870(13) 0.42771(10) 0.47117(10) 0.0227(2) Uani 1 1 d . . . H10A H -0.0463 0.3709 0.4141 0.027 Uiso 1 1 calc R . . H10B H 0.0663 0.3870 0.5195 0.027 Uiso 1 1 calc R . . C11 C -0.53591(13) 0.40316(10) 0.61495(11) 0.0236(3) Uani 1 1 d . . . N12 N -0.64911(12) 0.35406(10) 0.62268(10) 0.0306(3) Uani 1 1 d . . . C13 C 0.08175(12) 0.71773(9) 0.68839(10) 0.0208(2) Uani 1 1 d . . . C14 C 0.03882(14) 0.67927(11) 0.80835(10) 0.0256(3) Uani 1 1 d . . . H14A H 0.0671 0.5962 0.8196 0.038 Uiso 1 1 calc R . . H14B H -0.0702 0.6882 0.8189 0.038 Uiso 1 1 calc R . . H14C H 0.0922 0.7288 0.8634 0.038 Uiso 1 1 calc R . . C15 C 0.02338(16) 0.84173(10) 0.66060(12) 0.0311(3) Uani 1 1 d . . . H15A H 0.0542 0.8633 0.5838 0.047 Uiso 1 1 calc R . . H15B H 0.0655 0.8987 0.7145 0.047 Uiso 1 1 calc R . . H15C H -0.0869 0.8426 0.6657 0.047 Uiso 1 1 calc R . . C16 C 0.25521(14) 0.72153(12) 0.68777(12) 0.0326(3) Uani 1 1 d . . . H16A H 0.2950 0.6422 0.7029 0.049 Uiso 1 1 calc R . . H16B H 0.2905 0.7763 0.7463 0.049 Uiso 1 1 calc R . . H16C H 0.2906 0.7486 0.6137 0.049 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 C1 0.0198(5) 0.0222(5) 0.0208(5) 0.0035(4) -0.0036(4) -0.0015(4) C2 0.0232(5) 0.0181(5) 0.0182(5) 0.0003(4) -0.0047(4) -0.0004(4) C3 0.0227(5) 0.0184(5) 0.0166(5) 0.0018(4) -0.0013(4) 0.0017(4) C4 0.0199(5) 0.0176(5) 0.0154(5) 0.0018(4) -0.0013(4) 0.0001(4) C5 0.0218(5) 0.0183(5) 0.0197(5) -0.0015(4) -0.0015(4) 0.0011(4) C6 0.0202(5) 0.0236(5) 0.0198(5) 0.0016(4) 0.0000(4) 0.0023(4) N7 0.0206(5) 0.0195(4) 0.0182(4) -0.0024(4) 0.0026(4) -0.0019(3) C8 0.0240(5) 0.0226(5) 0.0229(6) -0.0020(4) 0.0075(5) -0.0032(4) C9 0.0292(6) 0.0244(5) 0.0196(5) -0.0013(4) 0.0054(5) 0.0004(5) C10 0.0251(5) 0.0201(5) 0.0228(6) -0.0036(4) 0.0018(4) 0.0009(4) C11 0.0229(6) 0.0234(5) 0.0245(6) 0.0002(4) -0.0025(5) 0.0010(4) N12 0.0243(5) 0.0297(5) 0.0378(6) -0.0013(5) -0.0009(4) -0.0034(4) C13 0.0224(5) 0.0188(5) 0.0213(5) -0.0020(4) 0.0007(4) -0.0020(4) C14 0.0289(6) 0.0278(6) 0.0202(5) -0.0016(5) -0.0024(5) -0.0063(5) C15 0.0444(7) 0.0177(5) 0.0312(7) 0.0000(5) -0.0034(6) -0.0016(5) C16 0.0234(6) 0.0393(7) 0.0351(7) -0.0106(6) 0.0018(5) -0.0095(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 C1 C6 1.3906(16) . ? C1 C2 1.3996(17) . ? C1 C11 1.4329(16) . ? C2 C3 1.3793(16) . ? C3 C4 1.4207(15) . ? C3 C10 1.4960(16) . ? C4 N7 1.3744(14) . ? C4 C5 1.4101(15) . ? C5 C6 1.3784(15) . ? N7 C8 1.4762(15) . ? N7 C13 1.4925(14) . ? C8 C9 1.5126(17) . ? C9 C10 1.5209(17) . ? C11 N12 1.1504(16) . ? C13 C15 1.5291(16) . ? C13 C14 1.5324(17) . ? C13 C16 1.5386(16) . ? 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 C6 C1 C2 118.43(10) . . ? C6 C1 C11 120.30(11) . . ? C2 C1 C11 121.26(11) . . ? C3 C2 C1 121.31(10) . . ? C2 C3 C4 120.56(10) . . ? C2 C3 C10 121.88(10) . . ? C4 C3 C10 117.53(10) . . ? N7 C4 C5 123.88(10) . . ? N7 C4 C3 118.86(10) . . ? C5 C4 C3 117.24(10) . . ? C6 C5 C4 121.35(10) . . ? C5 C6 C1 121.05(11) . . ? C4 N7 C8 119.82(9) . . ? C4 N7 C13 123.37(9) . . ? C8 N7 C13 115.81(9) . . ? N7 C8 C9 113.44(10) . . ? C8 C9 C10 108.22(9) . . ? C3 C10 C9 106.47(9) . . ? N12 C11 C1 178.63(14) . . ? N7 C13 C15 111.57(10) . . ? N7 C13 C14 111.00(9) . . ? C15 C13 C14 112.01(10) . . ? N7 C13 C16 108.70(9) . . ? C15 C13 C16 108.16(10) . . ? C14 C13 C16 105.11(10) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.185 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.037