# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 207/504 Nucleophilic Reactions of the Alkali Salts from 2-Substituted Alkenypropanedinitrile. Part 1. Karlsen,Songe,Sunsby Hagen,Kolsaker and Romming Two .cif files data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkins Trans 1' loop_ _publ_author_name 'Karlsen' 'Songe' 'Sunsby Hagen,' 'Kolsaker' 'Romming' data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-methyl-4,6-diphenyl-2-dicyanomethylene-1,2,5,6-tetrahydronicotinonitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 N4 O' _chemical_formula_weight 394.47 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P2(1)/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 7.09920(10) _cell_length_b 18.2612(3) _cell_length_c 16.4960(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.4720(10) _cell_angle_gamma 90.00 _cell_volume 2102.92(6) _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 0.7 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.078 _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 30820 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 32.04 _reflns_number_total 7287 _reflns_number_gt 5603 _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^)+(0.0690P)^2^+0.9200P] 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 7287 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 O1 O 0.25731(19) 0.51045(7) 0.00634(9) 0.0428(3) Uani 1 1 d . . . N1 N 0.23622(15) 0.40613(6) 0.38526(7) 0.0194(2) Uani 1 1 d . . . H1 H 0.343(3) 0.4226(11) 0.4147(13) 0.029(5) Uiso 1 1 d . . . N2 N -0.1049(2) 0.62656(7) 0.29313(9) 0.0353(3) Uani 1 1 d . . . N3 N 0.4013(2) 0.57436(7) 0.47994(9) 0.0357(3) Uani 1 1 d . . . N4 N -0.40179(18) 0.48467(7) 0.30747(9) 0.0311(3) Uani 1 1 d . . . C1 C 0.09855(16) 0.45375(6) 0.35497(7) 0.0178(2) Uani 1 1 d . . . C2 C -0.07486(17) 0.42303(6) 0.30208(7) 0.0186(2) Uani 1 1 d . . . C3 C -0.06546(17) 0.35848(6) 0.26216(7) 0.0181(2) Uani 1 1 d . . . C4 C 0.12754(17) 0.32173(6) 0.27269(7) 0.0188(2) Uani 1 1 d . . . H4A H 0.120(3) 0.2712(11) 0.2563(12) 0.027(4) Uiso 1 1 d . . . H4B H 0.206(2) 0.3476(9) 0.2330(11) 0.019(4) Uiso 1 1 d . . . C5 C 0.23198(16) 0.32782(6) 0.36272(7) 0.0170(2) Uani 1 1 d . . . C6 C -0.25641(18) 0.45833(7) 0.30382(8) 0.0216(2) Uani 1 1 d . . . C7 C 0.11456(18) 0.52828(7) 0.37360(8) 0.0213(2) Uani 1 1 d . . . C8 C -0.0101(2) 0.58178(7) 0.32945(8) 0.0244(2) Uani 1 1 d . . . C9 C 0.2739(2) 0.55466(7) 0.43181(9) 0.0251(3) Uani 1 1 d . . . C10 C 0.44093(18) 0.30284(7) 0.36990(9) 0.0237(2) Uani 1 1 d . . . H10A H 0.450(3) 0.2534(11) 0.3497(12) 0.026(4) Uiso 1 1 d . . . H10B H 0.506(3) 0.3366(11) 0.3390(13) 0.033(5) Uiso 1 1 d . . . H10C H 0.513(3) 0.3048(11) 0.4267(13) 0.031(5) Uiso 1 1 d . . . C11 C 0.12654(16) 0.28151(6) 0.41758(7) 0.0167(2) Uani 1 1 d . . . C12 C 0.01933(18) 0.31175(7) 0.47225(8) 0.0221(2) Uani 1 1 d . . . H12 H 0.010(3) 0.3648(11) 0.4791(12) 0.027(4) Uiso 1 1 d . . . C13 C -0.0771(2) 0.26621(8) 0.51931(9) 0.0277(3) Uani 1 1 d . . . H13 H -0.149(3) 0.2897(12) 0.5562(14) 0.038(5) Uiso 1 1 d . . . C14 C -0.0652(2) 0.19074(8) 0.51296(9) 0.0282(3) Uani 1 1 d . . . H14 H -0.130(3) 0.1599(12) 0.5462(13) 0.038(5) Uiso 1 1 d . . . C15 C 0.0417(2) 0.16002(7) 0.45882(8) 0.0248(2) Uani 1 1 d . . . H15 H 0.051(3) 0.1080(13) 0.4528(14) 0.041(5) Uiso 1 1 d . . . C16 C 0.13409(18) 0.20512(7) 0.41048(8) 0.0204(2) Uani 1 1 d . . . H16 H 0.204(3) 0.1822(10) 0.3739(12) 0.025(4) Uiso 1 1 d . . . C17 C -0.23374(17) 0.32237(7) 0.21279(7) 0.0210(2) Uani 1 1 d . . . C18 C -0.2628(2) 0.24761(8) 0.22399(9) 0.0260(3) Uani 1 1 d . . . H18 H -0.170(3) 0.2211(11) 0.2616(12) 0.028(4) Uiso 1 1 d . . . C19 C -0.4267(2) 0.21336(10) 0.18057(10) 0.0360(3) Uani 1 1 d . . . H19 H -0.449(3) 0.1607(12) 0.1920(12) 0.032(5) Uiso 1 1 d . . . C20 C -0.5575(2) 0.25296(12) 0.12473(11) 0.0423(4) Uani 1 1 d . . . H20 H -0.667(3) 0.2303(13) 0.0956(15) 0.048(6) Uiso 1 1 d . . . C21 C -0.5267(2) 0.32662(12) 0.11168(10) 0.0395(4) Uani 1 1 d . . . H21 H -0.615(3) 0.3550(14) 0.0692(15) 0.051(6) Uiso 1 1 d . . . C22 C -0.3667(2) 0.36199(9) 0.15575(8) 0.0286(3) Uani 1 1 d . . . H22 H -0.342(3) 0.4122(12) 0.1451(13) 0.036(5) Uiso 1 1 d . . . C23 C 0.2972(2) 0.52812(8) 0.07831(10) 0.0316(3) Uani 1 1 d . . . C24 C 0.1914(3) 0.49721(12) 0.14150(14) 0.0453(4) Uani 1 1 d . . . H24A H 0.138(4) 0.5380(18) 0.1698(19) 0.072(9) Uiso 1 1 d . . . H24B H 0.279(4) 0.4738(16) 0.1861(18) 0.064(8) Uiso 1 1 d . . . H24C H 0.086(4) 0.4672(17) 0.116(2) 0.073(9) Uiso 1 1 d . . . C25 C 0.4544(3) 0.58207(11) 0.10778(13) 0.0420(4) Uani 1 1 d . . . H25C H 0.390(5) 0.624(2) 0.125(2) 0.093(11) Uiso 1 1 d . . . H25B H 0.526(5) 0.5690(17) 0.159(2) 0.077(9) Uiso 1 1 d . . . H25A H 0.539(5) 0.590(2) 0.067(3) 0.102(12) 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 O1 0.0415(6) 0.0414(7) 0.0459(7) -0.0123(5) 0.0087(5) -0.0015(5) N1 0.0178(4) 0.0157(4) 0.0235(5) -0.0008(3) 0.0008(4) -0.0010(3) N2 0.0391(7) 0.0221(5) 0.0409(7) 0.0064(5) -0.0024(5) 0.0006(5) N3 0.0395(7) 0.0227(5) 0.0390(7) -0.0048(5) -0.0085(5) 0.0017(5) N4 0.0265(6) 0.0293(6) 0.0373(7) -0.0008(5) 0.0052(5) 0.0024(4) C1 0.0188(5) 0.0161(5) 0.0184(5) 0.0008(4) 0.0033(4) -0.0007(4) C2 0.0189(5) 0.0183(5) 0.0184(5) 0.0019(4) 0.0029(4) 0.0001(4) C3 0.0201(5) 0.0196(5) 0.0148(5) 0.0012(4) 0.0033(4) -0.0009(4) C4 0.0209(5) 0.0185(5) 0.0178(5) -0.0006(4) 0.0052(4) 0.0006(4) C5 0.0170(5) 0.0149(4) 0.0193(5) -0.0003(4) 0.0038(4) 0.0001(4) C6 0.0234(5) 0.0196(5) 0.0214(5) 0.0011(4) 0.0026(4) -0.0004(4) C7 0.0250(5) 0.0157(5) 0.0221(5) 0.0000(4) 0.0013(4) 0.0000(4) C8 0.0291(6) 0.0170(5) 0.0256(6) 0.0000(4) 0.0013(5) -0.0018(4) C9 0.0304(6) 0.0167(5) 0.0268(6) -0.0014(4) 0.0014(5) 0.0025(4) C10 0.0182(5) 0.0215(5) 0.0321(7) -0.0012(5) 0.0063(5) 0.0010(4) C11 0.0167(5) 0.0173(5) 0.0155(5) 0.0000(4) 0.0016(4) -0.0004(4) C12 0.0247(6) 0.0217(5) 0.0208(5) -0.0010(4) 0.0066(4) 0.0023(4) C13 0.0292(6) 0.0326(7) 0.0239(6) 0.0010(5) 0.0116(5) 0.0012(5) C14 0.0284(6) 0.0317(7) 0.0258(6) 0.0056(5) 0.0083(5) -0.0054(5) C15 0.0276(6) 0.0202(6) 0.0259(6) 0.0026(4) 0.0029(5) -0.0032(4) C16 0.0221(5) 0.0182(5) 0.0213(5) -0.0008(4) 0.0046(4) -0.0005(4) C17 0.0211(5) 0.0276(6) 0.0146(5) -0.0039(4) 0.0038(4) -0.0015(4) C18 0.0280(6) 0.0274(6) 0.0236(6) -0.0081(5) 0.0073(5) -0.0049(5) C19 0.0340(7) 0.0406(8) 0.0352(8) -0.0189(6) 0.0113(6) -0.0139(6) C20 0.0266(7) 0.0666(12) 0.0327(8) -0.0228(8) 0.0025(6) -0.0113(7) C21 0.0260(7) 0.0659(11) 0.0239(7) -0.0098(7) -0.0025(5) 0.0021(7) C22 0.0266(6) 0.0388(8) 0.0196(6) -0.0024(5) 0.0023(5) 0.0030(5) C23 0.0299(7) 0.0232(6) 0.0413(8) 0.0010(5) 0.0053(6) 0.0039(5) C24 0.0397(9) 0.0481(10) 0.0473(10) 0.0162(8) 0.0062(8) -0.0033(8) C25 0.0446(9) 0.0371(9) 0.0424(9) -0.0012(7) 0.0027(8) -0.0103(7) _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 C23 1.213(2) . ? N1 C1 1.3355(15) . ? N1 C5 1.4764(15) . ? N1 H1 0.88(2) . ? N2 C8 1.1549(18) . ? N3 C9 1.1479(18) . ? N4 C6 1.1501(18) . ? C1 C7 1.3955(16) . ? C1 C2 1.4836(16) . ? C2 C3 1.3578(17) . ? C2 C6 1.4460(17) . ? C3 C17 1.4736(16) . ? C3 C4 1.5071(16) . ? C4 C5 1.5387(17) . ? C4 H4A 0.960(19) . ? C4 H4B 1.048(17) . ? C5 C11 1.5300(16) . ? C5 C10 1.5359(17) . ? C7 C8 1.4262(18) . ? C7 C9 1.4278(18) . ? C10 H10A 0.969(19) . ? C10 H10B 0.97(2) . ? C10 H10C 0.98(2) . ? C11 C12 1.3953(17) . ? C11 C16 1.4017(16) . ? C12 C13 1.3987(19) . ? C12 H12 0.98(2) . ? C13 C14 1.386(2) . ? C13 H13 0.96(2) . ? C14 C15 1.391(2) . ? C14 H14 0.96(2) . ? C15 C16 1.3909(18) . ? C15 H15 0.96(2) . ? C16 H16 0.947(19) . ? C17 C18 1.3979(19) . ? C17 C22 1.4062(19) . ? C18 C19 1.398(2) . ? C18 H18 0.95(2) . ? C19 C20 1.387(3) . ? C19 H19 1.00(2) . ? C20 C21 1.386(3) . ? C20 H20 0.93(2) . ? C21 C22 1.391(2) . ? C21 H21 0.99(2) . ? C22 H22 0.96(2) . ? C23 C24 1.501(3) . ? C23 C25 1.502(2) . ? C24 H24A 0.99(3) . ? C24 H24B 0.97(3) . ? C24 H24C 0.96(3) . ? C25 H25C 0.96(4) . ? C25 H25B 0.94(3) . ? C25 H25A 0.99(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 C1 N1 C5 123.80(10) . . ? C1 N1 H1 119.0(13) . . ? C5 N1 H1 116.7(13) . . ? N1 C1 C7 121.87(11) . . ? N1 C1 C2 116.52(10) . . ? C7 C1 C2 121.60(10) . . ? C3 C2 C6 121.28(11) . . ? C3 C2 C1 120.32(11) . . ? C6 C2 C1 117.85(10) . . ? C2 C3 C17 123.38(11) . . ? C2 C3 C4 117.03(10) . . ? C17 C3 C4 119.55(10) . . ? C3 C4 C5 110.33(9) . . ? C3 C4 H4A 113.2(11) . . ? C5 C4 H4A 109.5(11) . . ? C3 C4 H4B 107.8(9) . . ? C5 C4 H4B 110.6(9) . . ? H4A C4 H4B 105.3(15) . . ? N1 C5 C11 112.09(9) . . ? N1 C5 C10 107.04(9) . . ? C11 C5 C10 111.08(10) . . ? N1 C5 C4 107.30(9) . . ? C11 C5 C4 109.23(9) . . ? C10 C5 C4 110.01(10) . . ? N4 C6 C2 177.49(14) . . ? C1 C7 C8 122.52(11) . . ? C1 C7 C9 120.00(11) . . ? C8 C7 C9 117.04(11) . . ? N2 C8 C7 177.33(15) . . ? N3 C9 C7 178.21(16) . . ? C5 C10 H10A 112.0(11) . . ? C5 C10 H10B 108.5(12) . . ? H10A C10 H10B 110.0(17) . . ? C5 C10 H10C 112.9(12) . . ? H10A C10 H10C 107.9(16) . . ? H10B C10 H10C 105.3(17) . . ? C12 C11 C16 118.78(11) . . ? C12 C11 C5 123.13(10) . . ? C16 C11 C5 118.06(10) . . ? C11 C12 C13 120.20(12) . . ? C11 C12 H12 121.5(11) . . ? C13 C12 H12 118.3(11) . . ? C14 C13 C12 120.43(12) . . ? C14 C13 H13 122.4(13) . . ? C12 C13 H13 117.1(13) . . ? C13 C14 C15 119.84(12) . . ? C13 C14 H14 120.0(13) . . ? C15 C14 H14 120.2(13) . . ? C16 C15 C14 119.90(12) . . ? C16 C15 H15 118.5(14) . . ? C14 C15 H15 121.6(14) . . ? C15 C16 C11 120.81(12) . . ? C15 C16 H16 117.4(11) . . ? C11 C16 H16 121.8(11) . . ? C18 C17 C22 119.58(12) . . ? C18 C17 C3 119.23(11) . . ? C22 C17 C3 121.18(12) . . ? C17 C18 C19 119.90(15) . . ? C17 C18 H18 118.8(12) . . ? C19 C18 H18 121.3(12) . . ? C20 C19 C18 120.09(16) . . ? C20 C19 H19 121.1(11) . . ? C18 C19 H19 118.8(11) . . ? C21 C20 C19 120.27(14) . . ? C21 C20 H20 119.4(15) . . ? C19 C20 H20 120.4(15) . . ? C20 C21 C22 120.40(16) . . ? C20 C21 H21 121.2(14) . . ? C22 C21 H21 118.3(14) . . ? C21 C22 C17 119.72(15) . . ? C21 C22 H22 120.7(12) . . ? C17 C22 H22 119.5(12) . . ? O1 C23 C24 121.48(16) . . ? O1 C23 C25 121.25(16) . . ? C24 C23 C25 117.27(16) . . ? C23 C24 H24A 109.2(18) . . ? C23 C24 H24B 111.0(17) . . ? H24A C24 H24B 103(2) . . ? C23 C24 H24C 110.7(19) . . ? H24A C24 H24C 107(2) . . ? H24B C24 H24C 115(3) . . ? C23 C25 H25C 105(2) . . ? C23 C25 H25B 112(2) . . ? H25C C25 H25B 99(3) . . ? C23 C25 H25A 112(2) . . ? H25C C25 H25A 118(3) . . ? H25B C25 H25A 111(3) . . ? 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 C7 -175.51(11) . . . . ? C5 N1 C1 C2 6.01(17) . . . . ? N1 C1 C2 C3 -23.89(17) . . . . ? C7 C1 C2 C3 157.62(12) . . . . ? N1 C1 C2 C6 147.67(11) . . . . ? C7 C1 C2 C6 -30.82(17) . . . . ? C6 C2 C3 C17 4.84(18) . . . . ? C1 C2 C3 C17 176.10(11) . . . . ? C6 C2 C3 C4 -172.75(11) . . . . ? C1 C2 C3 C4 -1.48(16) . . . . ? C2 C3 C4 C5 40.90(14) . . . . ? C17 C3 C4 C5 -136.78(11) . . . . ? C1 N1 C5 C11 -87.67(14) . . . . ? C1 N1 C5 C10 150.30(12) . . . . ? C1 N1 C5 C4 32.24(15) . . . . ? C3 C4 C5 N1 -53.78(12) . . . . ? C3 C4 C5 C11 67.94(12) . . . . ? C3 C4 C5 C10 -169.89(10) . . . . ? C3 C2 C6 N4 80(3) . . . . ? C1 C2 C6 N4 -92(3) . . . . ? N1 C1 C7 C8 166.87(12) . . . . ? C2 C1 C7 C8 -14.7(2) . . . . ? N1 C1 C7 C9 -5.29(19) . . . . ? C2 C1 C7 C9 173.12(12) . . . . ? C1 C7 C8 N2 -126(3) . . . . ? C9 C7 C8 N2 47(3) . . . . ? C1 C7 C9 N3 -45(5) . . . . ? C8 C7 C9 N3 143(5) . . . . ? N1 C5 C11 C12 10.44(15) . . . . ? C10 C5 C11 C12 130.14(12) . . . . ? C4 C5 C11 C12 -108.33(12) . . . . ? N1 C5 C11 C16 -171.48(10) . . . . ? C10 C5 C11 C16 -51.78(14) . . . . ? C4 C5 C11 C16 69.74(13) . . . . ? C16 C11 C12 C13 0.49(18) . . . . ? C5 C11 C12 C13 178.55(12) . . . . ? C11 C12 C13 C14 0.9(2) . . . . ? C12 C13 C14 C15 -0.7(2) . . . . ? C13 C14 C15 C16 -0.8(2) . . . . ? C14 C15 C16 C11 2.2(2) . . . . ? C12 C11 C16 C15 -2.03(18) . . . . ? C5 C11 C16 C15 179.80(11) . . . . ? C2 C3 C17 C18 -132.64(13) . . . . ? C4 C3 C17 C18 44.89(16) . . . . ? C2 C3 C17 C22 46.34(18) . . . . ? C4 C3 C17 C22 -136.14(12) . . . . ? C22 C17 C18 C19 -2.12(19) . . . . ? C3 C17 C18 C19 176.87(12) . . . . ? C17 C18 C19 C20 1.8(2) . . . . ? C18 C19 C20 C21 0.0(2) . . . . ? C19 C20 C21 C22 -1.5(2) . . . . ? C20 C21 C22 C17 1.1(2) . . . . ? C18 C17 C22 C21 0.6(2) . . . . ? C3 C17 C22 C21 -178.33(13) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 32.04 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.458 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.063 #=END data_9 _audit_creation_method SHELXL _chemical_name_systematic ; (E)-methyl(1-phenylpropenyl)propanedinitrile ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H12 N2' _chemical_formula_weight 196.25 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4135(2) _cell_length_b 7.6259(2) _cell_length_c 14.1780(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.3260(10) _cell_angle_gamma 90.00 _cell_volume 1119.05(4) _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 0.55 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method ? _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16689 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 33.13 _reflns_number_total 4189 _reflns_number_observed 3538 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 44 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.2400P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4145 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_obs 0.0487 _refine_ls_wR_factor_all 0.1247 _refine_ls_wR_factor_obs 0.1202 _refine_ls_goodness_of_fit_all 1.069 _refine_ls_goodness_of_fit_obs 1.107 _refine_ls_restrained_S_all 1.072 _refine_ls_restrained_S_obs 1.107 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.76142(9) 0.80466(11) 0.05465(6) 0.0332(2) Uani 1 d . . N2 N 0.58952(10) 0.32012(14) -0.03655(7) 0.0414(2) Uani 1 d . . C1 C 0.74800(8) 0.66079(12) 0.07464(6) 0.0240(2) Uani 1 d . . C2 C 0.65229(9) 0.38789(12) 0.02428(6) 0.0277(2) Uani 1 d . . C3 C 0.73040(8) 0.47599(11) 0.10429(5) 0.0213(2) Uani 1 d . . C4 C 0.86326(8) 0.38681(11) 0.12695(5) 0.02054(15) Uani 1 d . . C5 C 0.96181(8) 0.48992(11) 0.18876(6) 0.0215(2) Uani 1 d . . C6 C 1.04855(9) 0.59761(13) 0.14739(7) 0.0289(2) Uani 1 d . . H6 H 1.0447(14) 0.6053(20) 0.0776(11) 0.043(4) Uiso 1 d . . C7 C 1.14065(10) 0.69543(15) 0.20394(8) 0.0358(2) Uani 1 d . . H7 H 1.1999(16) 0.7705(23) 0.1741(12) 0.051(4) Uiso 1 d . . C8 C 1.14649(9) 0.68598(14) 0.30216(8) 0.0356(2) Uani 1 d . . H8 H 1.2099(15) 0.7572(21) 0.3420(11) 0.046(4) Uiso 1 d . . C9 C 1.06248(10) 0.57724(14) 0.34405(7) 0.0341(2) Uani 1 d . . H9 H 1.0695(15) 0.5691(20) 0.4136(11) 0.045(4) Uiso 1 d . . C10 C 0.97033(9) 0.47947(13) 0.28778(6) 0.0281(2) Uani 1 d . . H10 H 0.9102(13) 0.3992(19) 0.3170(10) 0.035(3) Uiso 1 d . . C11 C 0.65285(9) 0.47612(13) 0.19160(6) 0.0268(2) Uani 1 d . . H11A H 0.6401(14) 0.3534(19) 0.2094(10) 0.038(3) Uiso 1 d . . H11B H 0.7059(13) 0.5359(19) 0.2448(10) 0.038(3) Uiso 1 d . . H11C H 0.5701(13) 0.5386(18) 0.1760(9) 0.034(3) Uiso 1 d . . C12 C 0.88521(8) 0.22603(11) 0.09454(6) 0.0237(2) Uani 1 d . . H12 H 0.8163(12) 0.1662(17) 0.0532(9) 0.027(3) Uiso 1 d . . C13 C 1.00759(9) 0.12468(13) 0.11776(7) 0.0300(2) Uani 1 d . . H13A H 0.9880(15) 0.0032(21) 0.1331(11) 0.047(4) Uiso 1 d . . H13B H 1.0602(15) 0.1751(21) 0.1743(11) 0.044(4) Uiso 1 d . . H13C H 1.0565(14) 0.1223(18) 0.0627(11) 0.039(3) Uiso 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 0.0331(4) 0.0281(4) 0.0374(4) 0.0045(3) 0.0002(3) 0.0000(3) N2 0.0376(5) 0.0417(5) 0.0409(5) -0.0142(4) -0.0129(4) 0.0041(4) C1 0.0231(4) 0.0259(4) 0.0223(3) 0.0005(3) -0.0008(3) 0.0011(3) C2 0.0259(4) 0.0274(4) 0.0282(4) -0.0042(3) -0.0033(3) 0.0019(3) C3 0.0226(3) 0.0210(3) 0.0194(3) -0.0016(3) -0.0012(2) -0.0015(3) C4 0.0213(3) 0.0217(3) 0.0183(3) 0.0008(3) 0.0010(2) -0.0016(3) C5 0.0212(3) 0.0208(3) 0.0216(3) -0.0004(3) -0.0015(3) -0.0001(3) C6 0.0249(4) 0.0327(5) 0.0288(4) 0.0013(3) 0.0014(3) -0.0050(3) C7 0.0234(4) 0.0354(5) 0.0476(6) -0.0019(4) -0.0011(4) -0.0072(3) C8 0.0241(4) 0.0345(5) 0.0449(5) -0.0102(4) -0.0111(4) 0.0016(3) C9 0.0348(5) 0.0371(5) 0.0274(4) -0.0052(4) -0.0098(3) 0.0043(4) C10 0.0316(4) 0.0290(4) 0.0221(4) 0.0005(3) -0.0033(3) -0.0009(3) C11 0.0249(4) 0.0309(4) 0.0248(4) -0.0004(3) 0.0041(3) -0.0011(3) C12 0.0242(4) 0.0230(4) 0.0239(3) -0.0012(3) 0.0029(3) -0.0012(3) C13 0.0272(4) 0.0276(4) 0.0356(5) -0.0023(3) 0.0051(3) 0.0034(3) _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 C1 1.1456(12) . ? N2 C2 1.1462(12) . ? C1 C3 1.4877(12) . ? C2 C3 1.4821(11) . ? C3 C4 1.5434(11) . ? C3 C11 1.5508(12) . ? C4 C12 1.3378(12) . ? C4 C5 1.4972(11) . ? C5 C6 1.3967(12) . ? C5 C10 1.3991(12) . ? C6 C7 1.3963(13) . ? C6 H6 0.99(2) . ? C7 C8 1.389(2) . ? C7 H7 0.97(2) . ? C8 C9 1.386(2) . ? C8 H8 0.98(2) . ? C9 C10 1.3945(13) . ? C9 H9 0.98(2) . ? C10 H10 0.998(14) . ? C11 H11A 0.982(15) . ? C11 H11B 0.996(14) . ? C11 H11C 0.988(14) . ? C12 C13 1.4957(13) . ? C12 H12 0.987(12) . ? C13 H13A 0.98(2) . ? C13 H13B 1.00(2) . ? C13 H13C 0.978(15) . ? 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 N1 C1 C3 177.89(9) . . ? N2 C2 C3 178.49(10) . . ? C2 C3 C1 106.71(7) . . ? C2 C3 C4 111.31(7) . . ? C1 C3 C4 109.92(7) . . ? C2 C3 C11 108.73(7) . . ? C1 C3 C11 108.43(7) . . ? C4 C3 C11 111.58(7) . . ? C12 C4 C5 123.39(7) . . ? C12 C4 C3 121.03(7) . . ? C5 C4 C3 115.56(7) . . ? C6 C5 C10 118.84(8) . . ? C6 C5 C4 119.75(7) . . ? C10 C5 C4 121.40(8) . . ? C7 C6 C5 120.53(9) . . ? C7 C6 H6 119.5(9) . . ? C5 C6 H6 119.9(9) . . ? C8 C7 C6 119.96(10) . . ? C8 C7 H7 120.5(10) . . ? C6 C7 H7 119.6(10) . . ? C9 C8 C7 120.05(9) . . ? C9 C8 H8 120.0(9) . . ? C7 C8 H8 119.9(9) . . ? C8 C9 C10 120.12(9) . . ? C8 C9 H9 119.2(9) . . ? C10 C9 H9 120.7(9) . . ? C9 C10 C5 120.47(9) . . ? C9 C10 H10 120.9(8) . . ? C5 C10 H10 118.6(8) . . ? C3 C11 H11A 107.6(8) . . ? C3 C11 H11B 108.1(8) . . ? H11A C11 H11B 108.7(12) . . ? C3 C11 H11C 109.8(8) . . ? H11A C11 H11C 112.2(12) . . ? H11B C11 H11C 110.3(11) . . ? C4 C12 C13 124.87(8) . . ? C4 C12 H12 119.1(7) . . ? C13 C12 H12 116.0(7) . . ? C12 C13 H13A 110.2(9) . . ? C12 C13 H13B 110.9(9) . . ? H13A C13 H13B 107.2(13) . . ? C12 C13 H13C 109.9(8) . . ? H13A C13 H13C 107.5(12) . . ? H13B C13 H13C 111.1(12) . . ? 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 N2 C2 C3 C1 -101.2(40) . . . . ? N2 C2 C3 C4 138.9(40) . . . . ? N2 C2 C3 C11 15.6(40) . . . . ? N1 C1 C3 C2 145.9(25) . . . . ? N1 C1 C3 C4 -93.3(25) . . . . ? N1 C1 C3 C11 28.9(25) . . . . ? C2 C3 C4 C12 -16.47(11) . . . . ? C1 C3 C4 C12 -134.48(8) . . . . ? C11 C3 C4 C12 105.19(9) . . . . ? C2 C3 C4 C5 165.15(7) . . . . ? C1 C3 C4 C5 47.14(9) . . . . ? C11 C3 C4 C5 -73.19(9) . . . . ? C12 C4 C5 C6 88.31(11) . . . . ? C3 C4 C5 C6 -93.35(9) . . . . ? C12 C4 C5 C10 -90.91(11) . . . . ? C3 C4 C5 C10 87.43(10) . . . . ? C10 C5 C6 C7 -1.10(14) . . . . ? C4 C5 C6 C7 179.65(9) . . . . ? C5 C6 C7 C8 0.0(2) . . . . ? C6 C7 C8 C9 1.1(2) . . . . ? C7 C8 C9 C10 -1.2(2) . . . . ? C8 C9 C10 C5 0.07(15) . . . . ? C6 C5 C10 C9 1.06(14) . . . . ? C4 C5 C10 C9 -179.71(8) . . . . ? C5 C4 C12 C13 2.32(13) . . . . ? C3 C4 C12 C13 -175.93(8) . . . . ? _refine_diff_density_max 0.365 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.040