# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Francois Diederich' _publ_contact_author_email DIEDERICH@ORG.CHEM.ETHZ.CH _publ_section_title ; New donor-acceptor chromophores by formal [2+2] cycloaddition of donor-substituted alkynes to dicyanovinyl derivatives ; loop_ _publ_author_name 'Francois Diederich' 'Peter Jarowski' # Attachment 'deposit.cif' data_10 _database_code_depnum_ccdc_archive 'CCDC 699249' _chemical_compound_source 'LOC ETH Zurich' _exptl_crystal_description plate _exptl_crystal_size_max .2 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .05 _exptl_crystal_F_000 656.0 _exptl_crystal_colour amber _cell_measurement_temperature 173 _refine_ls_hydrogen_treatment refall _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.09765 _diffrn_orient_matrix_UB_12 0.01830 _diffrn_orient_matrix_UB_13 0.03887 _diffrn_orient_matrix_UB_21 -0.02528 _diffrn_orient_matrix_UB_22 0.02457 _diffrn_orient_matrix_UB_23 0.05193 _diffrn_orient_matrix_UB_31 0.03044 _diffrn_orient_matrix_UB_32 -0.07113 _diffrn_orient_matrix_UB_33 0.04846 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 305.425 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C20 H23 N3 ' _chemical_formula_sum 'C20 H23 N3 ' _chemical_name_systematic ; (E)-2-(3-cyclohexyl-1-(4-(dimethylamino)phenyl)allylidene)malononitrile ; _cell_length_a 10.0678(3) _cell_length_b 15.9325(5) _cell_length_c 11.7652(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.406(2) _cell_angle_gamma 90.00 _cell_volume 1757.01(10) _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_number 5645 _diffrn_reflns_theta_max 25.37 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_full 25.37 _cell_measurement_reflns_used 7006 _cell_measurement_theta_min 2.425 _cell_measurement_theta_max 25.350 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97(Altomare et al., J. Appl. Cryst.,1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.069 _reflns_number_total 3185 _reflns_number_gt 2515 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3185 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1459 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.069 _refine_ls_shift/su_mean 0.003 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 N12 N 0.76075(16) 0.12204(12) 0.44830(13) 0.0527(4) Uani 1 1 d . . . N14 N 0.91073(16) 0.09339(10) 0.84220(14) 0.0520(4) Uani 1 1 d . . . N21 N 0.39565(14) 0.10996(8) 1.04581(11) 0.0357(3) Uani 1 1 d . . . C1 C 0.55399(15) 0.11085(8) 0.63029(13) 0.0303(3) Uani 1 1 d . . . C2 C 0.44304(16) 0.10909(9) 0.50778(13) 0.0320(3) Uani 1 1 d . . . C3 C 0.31134(16) 0.13892(10) 0.47947(13) 0.0339(4) Uani 1 1 d . . . C4 C 0.20068(15) 0.14086(10) 0.35344(13) 0.0339(4) Uani 1 1 d . . . C5 C 0.18028(18) 0.23100(11) 0.30350(16) 0.0437(4) Uani 1 1 d . . . C6 C 0.0675(2) 0.23482(13) 0.17475(18) 0.0573(5) Uani 1 1 d . . . C7 C -0.0730(2) 0.19772(13) 0.1697(2) 0.0608(6) Uani 1 1 d . . . C8 C -0.0540(2) 0.10906(12) 0.2216(2) 0.0568(5) Uani 1 1 d . . . C9 C 0.05819(18) 0.10514(11) 0.34988(17) 0.0450(4) Uani 1 1 d . . . C10 C 0.69461(16) 0.11051(9) 0.64012(13) 0.0331(3) Uani 1 1 d . . . C11 C 0.73196(15) 0.11656(10) 0.53390(14) 0.0375(4) Uani 1 1 d . . . C13 C 0.81344(16) 0.10115(9) 0.75387(14) 0.0369(4) Uani 1 1 d . . . C15 C 0.51344(15) 0.11226(8) 0.73734(12) 0.0304(3) Uani 1 1 d . . . C16 C 0.58609(15) 0.16150(9) 0.84115(12) 0.0307(3) Uani 1 1 d . . . C17 C 0.54793(15) 0.16153(9) 0.94174(13) 0.0315(3) Uani 1 1 d . . . C18 C 0.43484(15) 0.11108(8) 0.94688(12) 0.0302(3) Uani 1 1 d . . . C19 C 0.36126(16) 0.06200(9) 0.84256(13) 0.0328(3) Uani 1 1 d . . . C20 C 0.39864(16) 0.06391(9) 0.74148(13) 0.0332(3) Uani 1 1 d . . . C22 C 0.4788(2) 0.15450(12) 1.15649(15) 0.0432(4) Uani 1 1 d . . . C23 C 0.28016(19) 0.05604(11) 1.04807(16) 0.0409(4) Uani 1 1 d . . . H2 H 0.4705(17) 0.0863(11) 0.4446(15) 0.033(4) Uiso 1 1 d . . . H3 H 0.2853(17) 0.1637(10) 0.5448(15) 0.032(4) Uiso 1 1 d . . . H4 H 0.2391(18) 0.1071(11) 0.3027(15) 0.035(4) Uiso 1 1 d . . . H19 H 0.2801(19) 0.0285(11) 0.8426(14) 0.036(4) Uiso 1 1 d . . . H16 H 0.6624(18) 0.1977(11) 0.8428(14) 0.034(4) Uiso 1 1 d . . . H17 H 0.5959(18) 0.1982(12) 1.0091(15) 0.037(4) Uiso 1 1 d . . . H5A H 0.270(2) 0.2545(12) 0.3038(17) 0.046(5) Uiso 1 1 d . . . H9A H 0.0215(19) 0.1438(12) 0.4055(16) 0.045(5) Uiso 1 1 d . . . H20 H 0.3473(18) 0.0286(12) 0.6743(16) 0.040(4) Uiso 1 1 d . . . H9B H 0.074(2) 0.0471(13) 0.3800(16) 0.046(5) Uiso 1 1 d . . . H8A H -0.027(2) 0.0713(14) 0.1659(18) 0.051(5) Uiso 1 1 d . . . H6A H 0.104(3) 0.1983(17) 0.113(2) 0.076(7) Uiso 1 1 d . . . H23A H 0.191(2) 0.0713(14) 0.9812(19) 0.056(5) Uiso 1 1 d . . . H8B H -0.143(3) 0.0868(15) 0.225(2) 0.065(6) Uiso 1 1 d . . . H23B H 0.269(3) 0.0604(17) 1.129(2) 0.078(7) Uiso 1 1 d . . . H23C H 0.299(2) -0.0033(15) 1.0367(18) 0.056(5) Uiso 1 1 d . . . H5B H 0.146(2) 0.2656(13) 0.3619(17) 0.050(5) Uiso 1 1 d . . . H22 H 0.439(3) 0.1457(17) 1.219(2) 0.084(8) Uiso 1 1 d . . . H7 H -0.115(3) 0.2319(17) 0.218(2) 0.074(7) Uiso 1 1 d . . . H6B H 0.054(2) 0.2941(15) 0.1471(18) 0.057(5) Uiso 1 1 d . . . H7B H -0.146(3) 0.1976(18) 0.083(2) 0.088(8) Uiso 1 1 d . . . H22B H 0.575(3) 0.1365(17) 1.191(2) 0.077(7) Uiso 1 1 d . . . H22C H 0.476(3) 0.2155(18) 1.142(2) 0.077(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 N12 0.0425(8) 0.0747(11) 0.0431(8) -0.0083(7) 0.0182(7) -0.0083(7) N14 0.0383(8) 0.0611(10) 0.0476(8) 0.0062(7) 0.0050(7) 0.0065(7) N21 0.0395(7) 0.0385(7) 0.0289(6) -0.0023(5) 0.0121(5) -0.0031(5) C1 0.0329(8) 0.0253(7) 0.0302(7) 0.0003(5) 0.0085(6) 0.0005(5) C2 0.0330(8) 0.0337(8) 0.0290(7) -0.0011(6) 0.0109(6) -0.0022(6) C3 0.0341(8) 0.0367(8) 0.0305(7) -0.0019(6) 0.0114(6) -0.0014(6) C4 0.0290(7) 0.0369(8) 0.0337(8) -0.0047(6) 0.0089(6) 0.0005(6) C5 0.0360(8) 0.0419(9) 0.0446(9) 0.0001(7) 0.0044(7) -0.0068(7) C6 0.0494(10) 0.0522(11) 0.0511(11) 0.0097(9) -0.0045(9) 0.0036(9) C7 0.0372(9) 0.0524(11) 0.0696(12) -0.0075(9) -0.0080(9) 0.0060(8) C8 0.0316(9) 0.0467(11) 0.0772(14) -0.0154(9) 0.0023(9) -0.0061(8) C9 0.0355(9) 0.0394(9) 0.0595(11) -0.0047(8) 0.0166(8) -0.0057(7) C10 0.0306(7) 0.0331(8) 0.0331(7) 0.0000(6) 0.0086(6) -0.0009(6) C11 0.0301(8) 0.0420(9) 0.0381(8) -0.0038(6) 0.0096(6) -0.0024(6) C13 0.0321(8) 0.0373(8) 0.0393(8) 0.0023(6) 0.0109(7) 0.0019(6) C15 0.0300(7) 0.0289(7) 0.0285(7) 0.0026(5) 0.0063(6) 0.0007(5) C16 0.0283(7) 0.0280(7) 0.0312(7) 0.0023(5) 0.0055(6) -0.0003(6) C17 0.0316(7) 0.0291(7) 0.0285(7) -0.0029(5) 0.0045(6) -0.0004(6) C18 0.0321(7) 0.0274(7) 0.0289(7) 0.0034(5) 0.0084(6) 0.0043(5) C19 0.0350(7) 0.0294(7) 0.0328(7) 0.0006(5) 0.0108(6) -0.0056(6) C20 0.0349(7) 0.0313(7) 0.0291(7) -0.0022(6) 0.0065(6) -0.0044(6) C22 0.0517(11) 0.0460(10) 0.0303(8) -0.0054(7) 0.0132(7) -0.0054(8) C23 0.0437(9) 0.0423(10) 0.0402(9) 0.0000(7) 0.0197(7) -0.0041(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 N12 C11 1.148(2) . ? N14 C13 1.145(2) . ? N21 C18 1.3586(19) . ? N21 C23 1.454(2) . ? N21 C22 1.451(2) . ? C1 C10 1.378(2) . ? C1 C15 1.459(2) . ? C1 C2 1.4666(19) . ? C2 C3 1.331(2) . ? C3 C4 1.495(2) . ? C4 C9 1.530(2) . ? C4 C5 1.537(2) . ? C5 C6 1.527(2) . ? C6 C7 1.514(3) . ? C7 C8 1.523(3) . ? C8 C9 1.521(3) . ? C10 C11 1.434(2) . ? C10 C13 1.441(2) . ? C15 C20 1.404(2) . ? C15 C16 1.4107(19) . ? C16 C17 1.371(2) . ? C17 C18 1.413(2) . ? C18 C19 1.415(2) . ? C19 C20 1.372(2) . ? C2 H2 0.953(17) . ? C3 H3 0.981(17) . ? C4 H4 0.982(18) . ? C5 H5A 0.98(2) . ? C5 H5B 1.03(2) . ? C6 H6A 1.09(3) . ? C6 H6B 0.99(2) . ? C7 H7 0.99(3) . ? C7 H7B 1.02(3) . ? C8 H8A 0.99(2) . ? C8 H8B 0.98(3) . ? C9 H9A 1.06(2) . ? C9 H9B 0.98(2) . ? C16 H16 0.955(18) . ? C17 H17 0.961(18) . ? C19 H19 0.977(18) . ? C20 H20 0.954(18) . ? C22 H22 0.96(3) . ? C22 H22B 0.95(3) . ? C22 H22C 0.99(3) . ? C23 H23A 0.98(2) . ? C23 H23B 1.00(3) . ? C23 H23C 0.98(2) . ? 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 C18 N21 C23 120.51(12) . . ? C18 N21 C22 120.64(13) . . ? C23 N21 C22 118.43(13) . . ? C10 C1 C15 122.03(13) . . ? C10 C1 C2 118.24(14) . . ? C15 C1 C2 119.73(13) . . ? C3 C2 C1 124.81(14) . . ? C2 C3 C4 124.68(14) . . ? C3 C4 C9 111.80(13) . . ? C3 C4 C5 110.23(12) . . ? C9 C4 C5 110.12(13) . . ? C6 C5 C4 111.33(14) . . ? C7 C6 C5 111.67(18) . . ? C6 C7 C8 111.57(16) . . ? C9 C8 C7 112.02(14) . . ? C8 C9 C4 111.16(16) . . ? C1 C10 C11 121.00(13) . . ? C1 C10 C13 123.91(14) . . ? C11 C10 C13 115.06(13) . . ? N12 C11 C10 179.26(18) . . ? N14 C13 C10 177.79(18) . . ? C20 C15 C16 116.63(13) . . ? C20 C15 C1 120.96(12) . . ? C16 C15 C1 122.41(13) . . ? C17 C16 C15 121.82(13) . . ? C16 C17 C18 121.39(13) . . ? N21 C18 C17 122.32(13) . . ? N21 C18 C19 120.79(13) . . ? C17 C18 C19 116.88(13) . . ? C20 C19 C18 121.12(14) . . ? C19 C20 C15 122.12(13) . . ? C3 C2 H2 119.1(10) . . ? C1 C2 H2 116.1(10) . . ? C2 C3 H3 118.3(9) . . ? C4 C3 H3 116.9(9) . . ? C3 C4 H4 106.0(10) . . ? C9 C4 H4 110.7(10) . . ? C5 C4 H4 107.8(10) . . ? C6 C5 H5A 109.9(11) . . ? C4 C5 H5A 111.2(11) . . ? C6 C5 H5B 109.2(10) . . ? C4 C5 H5B 105.9(11) . . ? H5A C5 H5B 109.2(16) . . ? C7 C6 H6A 107.6(13) . . ? C5 C6 H6A 109.1(12) . . ? C7 C6 H6B 110.1(12) . . ? C5 C6 H6B 109.1(12) . . ? H6A C6 H6B 109.2(19) . . ? C6 C7 H7 110.6(15) . . ? C8 C7 H7 107.4(15) . . ? C6 C7 H7B 111.6(15) . . ? C8 C7 H7B 109.8(16) . . ? H7 C7 H7B 106(2) . . ? C9 C8 H8A 110.4(11) . . ? C7 C8 H8A 108.8(12) . . ? C9 C8 H8B 107.7(13) . . ? C7 C8 H8B 111.7(14) . . ? H8A C8 H8B 106.2(18) . . ? C8 C9 H9A 106.8(10) . . ? C4 C9 H9A 107.6(10) . . ? C8 C9 H9B 111.0(11) . . ? C4 C9 H9B 108.5(11) . . ? H9A C9 H9B 111.7(15) . . ? C17 C16 H16 117.3(10) . . ? C15 C16 H16 120.8(10) . . ? C16 C17 H17 119.8(10) . . ? C18 C17 H17 118.7(10) . . ? C20 C19 H19 120.4(9) . . ? C18 C19 H19 118.4(9) . . ? C19 C20 H20 117.9(11) . . ? C15 C20 H20 119.9(11) . . ? N21 C22 H22 110.3(16) . . ? N21 C22 H22B 113.6(16) . . ? H22 C22 H22B 106(2) . . ? N21 C22 H22C 110.8(14) . . ? H22 C22 H22C 107(2) . . ? H22B C22 H22C 109(2) . . ? N21 C23 H23A 109.8(13) . . ? N21 C23 H23B 110.2(15) . . ? H23A C23 H23B 111.0(19) . . ? N21 C23 H23C 111.8(13) . . ? H23A C23 H23C 107.1(18) . . ? H23B C23 H23C 106.9(19) . . ? 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 C10 C1 C2 C3 -154.22(15) . . . . ? C15 C1 C2 C3 26.2(2) . . . . ? C1 C2 C3 C4 176.85(14) . . . . ? C2 C3 C4 C9 131.03(16) . . . . ? C2 C3 C4 C5 -106.14(18) . . . . ? C3 C4 C5 C6 -179.90(15) . . . . ? C9 C4 C5 C6 -56.1(2) . . . . ? C4 C5 C6 C7 55.4(2) . . . . ? C5 C6 C7 C8 -53.9(3) . . . . ? C6 C7 C8 C9 54.1(3) . . . . ? C7 C8 C9 C4 -55.5(2) . . . . ? C3 C4 C9 C8 178.93(14) . . . . ? C5 C4 C9 C8 56.04(18) . . . . ? C15 C1 C10 C11 -174.46(13) . . . . ? C2 C1 C10 C11 6.0(2) . . . . ? C15 C1 C10 C13 7.9(2) . . . . ? C2 C1 C10 C13 -171.63(14) . . . . ? C1 C10 C11 N12 40(15) . . . . ? C13 C10 C11 N12 -142(15) . . . . ? C1 C10 C13 N14 170(4) . . . . ? C11 C10 C13 N14 -8(4) . . . . ? C10 C1 C15 C20 -139.83(15) . . . . ? C2 C1 C15 C20 39.71(19) . . . . ? C10 C1 C15 C16 40.2(2) . . . . ? C2 C1 C15 C16 -140.29(14) . . . . ? C20 C15 C16 C17 0.8(2) . . . . ? C1 C15 C16 C17 -179.24(12) . . . . ? C15 C16 C17 C18 0.9(2) . . . . ? C23 N21 C18 C17 -178.97(14) . . . . ? C22 N21 C18 C17 -6.5(2) . . . . ? C23 N21 C18 C19 2.1(2) . . . . ? C22 N21 C18 C19 174.57(14) . . . . ? C16 C17 C18 N21 179.77(13) . . . . ? C16 C17 C18 C19 -1.2(2) . . . . ? N21 C18 C19 C20 178.85(13) . . . . ? C17 C18 C19 C20 -0.1(2) . . . . ? C18 C19 C20 C15 1.9(2) . . . . ? C16 C15 C20 C19 -2.2(2) . . . . ? C1 C15 C20 C19 177.82(13) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.178 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ; _chemical_name_common ;(E)-2-(3-cyclohexyl-1-(4- (dimethylamino)phenyl)allylidene)malononitrile ; # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_3e _database_code_depnum_ccdc_archive 'CCDC 699250' _audit_creation_method maXus _chemical_compound_source 'LOC ETH Zurich' _exptl_crystal_description plate _exptl_crystal_size_max .2 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .05 _exptl_crystal_F_000 768 _exptl_crystal_colour brown _cell_measurement_temperature 223 _refine_ls_hydrogen_treatment constr _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.04027 _diffrn_orient_matrix_UB_12 -0.09212 _diffrn_orient_matrix_UB_13 -0.03263 _diffrn_orient_matrix_UB_21 -0.04075 _diffrn_orient_matrix_UB_22 0.02356 _diffrn_orient_matrix_UB_23 -0.11679 _diffrn_orient_matrix_UB_31 0.03692 _diffrn_orient_matrix_UB_32 0.01667 _diffrn_orient_matrix_UB_33 -0.00952 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 378.273 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X,+Y+ 1/2,-Z+ 1/2' '+X,-Y+ 1/2,+Z+ 1/2' _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C20 H16 Br N3 ' _chemical_formula_sum 'C20 H16 Br N3 ' _chemical_name_systematic ; (E)-2-(3-(4-bromophenyl)-1-(4-(dimethylamino)phenyl)allylidene)malononitrile ; _cell_length_a 9.4778(3) _cell_length_b 7.9420(3) _cell_length_c 24.0757(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.4125(14) _cell_angle_gamma 90.00 _cell_volume 1809.03(11) _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_number 6188 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_full 27.45 _cell_measurement_reflns_used 28352 _cell_measurement_theta_min 2.425 _cell_measurement_theta_max 27.485 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97(Altomare et al., J. Appl. Cryst.,1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _exptl_absorpt_coefficient_mu 2.277 _reflns_number_total 3690 _reflns_number_gt 2650 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3690 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1684 _refine_ls_wR_factor_gt 0.1464 _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 Br24 Br -0.70983(4) 0.45791(7) 0.433492(17) 0.0785(2) Uani 1 1 d . . . N19 N 0.1762(4) -0.0253(5) 0.47192(14) 0.0798(10) Uani 1 1 d . . . N20 N 0.3993(4) -0.1252(6) 0.32404(15) 0.0903(12) Uani 1 1 d . . . C1 C 0.0734(3) 0.0863(4) 0.33405(13) 0.0460(7) Uani 1 1 d . . . C2 C 0.0920(3) 0.1237(4) 0.27507(12) 0.0418(6) Uani 1 1 d . . . C3 C -0.0108(3) 0.0870(4) 0.23296(12) 0.0441(6) Uani 1 1 d . . . C4 C 0.0105(3) 0.1175(4) 0.17763(12) 0.0468(7) Uani 1 1 d . . . C5 C 0.1374(3) 0.1904(4) 0.16125(12) 0.0435(6) Uani 1 1 d . . . C6 C 0.2394(3) 0.2331(4) 0.20384(12) 0.0458(7) Uani 1 1 d . . . C7 C 0.2173(3) 0.1988(4) 0.25872(12) 0.0450(7) Uani 1 1 d . . . C8 C -0.0556(3) 0.1303(4) 0.36022(13) 0.0476(7) Uani 1 1 d . . . C9 C -0.1586(3) 0.2272(4) 0.33633(12) 0.0459(7) Uani 1 1 d . . . C10 C -0.2909(3) 0.2766(4) 0.36073(12) 0.0437(6) Uani 1 1 d . . . C11 C -0.3911(3) 0.3655(4) 0.32780(12) 0.0467(7) Uani 1 1 d . . . C12 C -0.5156(3) 0.4192(4) 0.34907(13) 0.0506(7) Uani 1 1 d . . . C13 C -0.5413(3) 0.3808(4) 0.40328(13) 0.0509(7) Uani 1 1 d . . . C14 C -0.4445(3) 0.2912(5) 0.43718(13) 0.0575(8) Uani 1 1 d . . . C15 C -0.3195(3) 0.2392(4) 0.41588(13) 0.0520(7) Uani 1 1 d . . . C16 C 0.1824(4) 0.0118(4) 0.36562(13) 0.0512(8) Uani 1 1 d . . . C17 C 0.3034(4) -0.0600(5) 0.34209(15) 0.0626(9) Uani 1 1 d . . . C18 C 0.1784(4) -0.0083(5) 0.42491(16) 0.0604(9) Uani 1 1 d . . . N21 N 0.1594(3) 0.2196(4) 0.10629(10) 0.0544(7) Uani 1 1 d . . . C22 C 0.0683(4) 0.1428(5) 0.06310(13) 0.0634(9) Uani 1 1 d . . . C23 C 0.2964(3) 0.2765(5) 0.08961(15) 0.0613(9) Uani 1 1 d . . . H3 H -0.0997 0.0397 0.2420 0.053 Uiso 1 1 d R . . H4 H -0.0612 0.0877 0.1495 0.056 Uiso 1 1 d R . . H6 H 0.3260 0.2868 0.1950 0.055 Uiso 1 1 d R . . H7 H 0.2912 0.2275 0.2861 0.054 Uiso 1 1 d R . . H8 H -0.0716 0.0875 0.3966 0.057 Uiso 1 1 d R . . H9 H -0.1481 0.2730 0.2999 0.055 Uiso 1 1 d R . . H11 H -0.3753 0.3927 0.2898 0.056 Uiso 1 1 d R . . H12 H -0.5824 0.4830 0.3261 0.061 Uiso 1 1 d R . . H14 H -0.4649 0.2664 0.4749 0.069 Uiso 1 1 d R . . H15 H -0.2523 0.1779 0.4394 0.062 Uiso 1 1 d R . . H22A H 0.0982 0.1756 0.0273 0.076 Uiso 1 1 d R . . H22B H -0.0275 0.1782 0.0667 0.076 Uiso 1 1 d R . . H22C H 0.0742 0.0226 0.0667 0.076 Uiso 1 1 d R . . H23A H 0.2944 0.2902 0.0499 0.074 Uiso 1 1 d R . . H23B H 0.3675 0.1955 0.1010 0.074 Uiso 1 1 d R . . H23C H 0.3180 0.3825 0.1073 0.074 Uiso 1 1 d 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 Br24 0.0555(3) 0.1075(4) 0.0741(3) 0.0004(2) 0.01676(19) 0.01855(19) N19 0.094(3) 0.096(3) 0.0481(18) 0.0084(17) -0.0075(16) 0.0067(19) N20 0.080(2) 0.117(3) 0.073(2) 0.012(2) 0.0058(17) 0.046(2) C1 0.0489(16) 0.0421(15) 0.0471(15) -0.0046(13) 0.0036(12) -0.0021(12) C2 0.0403(14) 0.0421(15) 0.0428(14) -0.0046(12) 0.0019(11) -0.0002(11) C3 0.0379(14) 0.0466(16) 0.0479(15) -0.0027(14) 0.0047(11) -0.0028(12) C4 0.0428(15) 0.0502(17) 0.0467(15) -0.0026(14) -0.0024(12) -0.0037(13) C5 0.0436(15) 0.0396(15) 0.0478(15) -0.0013(13) 0.0062(11) 0.0053(11) C6 0.0358(14) 0.0467(16) 0.0553(17) -0.0014(14) 0.0062(12) -0.0010(12) C7 0.0371(14) 0.0470(16) 0.0504(16) -0.0066(13) -0.0016(11) 0.0010(12) C8 0.0512(16) 0.0453(17) 0.0467(15) 0.0006(14) 0.0059(12) -0.0026(13) C9 0.0487(15) 0.0470(16) 0.0425(14) -0.0007(13) 0.0072(11) -0.0047(13) C10 0.0446(14) 0.0432(15) 0.0437(14) -0.0002(13) 0.0057(11) -0.0065(12) C11 0.0507(16) 0.0485(17) 0.0411(14) 0.0009(13) 0.0029(12) -0.0055(13) C12 0.0500(17) 0.0497(18) 0.0513(17) 0.0033(14) -0.0049(13) -0.0004(13) C13 0.0419(15) 0.0560(18) 0.0550(17) -0.0052(15) 0.0036(12) -0.0016(13) C14 0.0578(19) 0.070(2) 0.0449(16) 0.0020(16) 0.0087(13) -0.0015(16) C15 0.0517(16) 0.0593(19) 0.0453(15) 0.0074(15) 0.0054(12) 0.0065(14) C16 0.0541(18) 0.0547(18) 0.0443(16) -0.0008(14) -0.0003(13) 0.0085(14) C17 0.063(2) 0.074(2) 0.0496(18) 0.0082(17) -0.0040(15) 0.0184(18) C18 0.065(2) 0.063(2) 0.052(2) -0.0007(17) -0.0023(16) 0.0060(16) N21 0.0499(14) 0.0683(18) 0.0455(13) 0.0042(13) 0.0067(10) -0.0026(12) C22 0.064(2) 0.083(3) 0.0432(16) -0.0004(18) 0.0048(14) -0.0048(19) C23 0.0530(18) 0.073(2) 0.0588(19) 0.0156(18) 0.0115(14) -0.0015(16) _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 Br24 C13 1.895(3) . ? N19 C18 1.141(5) . ? N20 C17 1.153(5) . ? C1 C16 1.379(5) . ? C1 C8 1.451(4) . ? C1 C2 1.471(4) . ? C2 C3 1.394(4) . ? C2 C7 1.406(4) . ? C3 C4 1.381(4) . ? C4 C5 1.412(4) . ? C5 N21 1.372(4) . ? C5 C6 1.408(4) . ? C6 C7 1.377(4) . ? C8 C9 1.345(4) . ? C9 C10 1.469(4) . ? C10 C11 1.393(4) . ? C10 C15 1.403(4) . ? C11 C12 1.381(4) . ? C12 C13 1.376(5) . ? C13 C14 1.388(5) . ? C14 C15 1.381(4) . ? C16 C17 1.428(5) . ? C16 C18 1.439(5) . ? N21 C22 1.446(4) . ? N21 C23 1.454(4) . ? C3 H3 0.9600 . ? C4 H4 0.9600 . ? C6 H6 0.9600 . ? C7 H7 0.9599 . ? C8 H8 0.9601 . ? C9 H9 0.9601 . ? C11 H11 0.9599 . ? C12 H12 0.9599 . ? C14 H14 0.9598 . ? C15 H15 0.9601 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9601 . ? C23 H23B 0.9600 . ? C23 H23C 0.9601 . ? 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 C16 C1 C8 119.2(3) . . ? C16 C1 C2 119.3(3) . . ? C8 C1 C2 121.5(3) . . ? C3 C2 C7 116.7(3) . . ? C3 C2 C1 122.7(3) . . ? C7 C2 C1 120.5(2) . . ? C4 C3 C2 121.9(3) . . ? C3 C4 C5 121.2(3) . . ? N21 C5 C6 121.7(3) . . ? N21 C5 C4 121.3(3) . . ? C6 C5 C4 117.0(3) . . ? C7 C6 C5 120.9(3) . . ? C6 C7 C2 122.1(3) . . ? C9 C8 C1 124.1(3) . . ? C8 C9 C10 126.6(3) . . ? C11 C10 C15 118.8(3) . . ? C11 C10 C9 118.5(3) . . ? C15 C10 C9 122.7(3) . . ? C12 C11 C10 121.0(3) . . ? C13 C12 C11 119.1(3) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 Br24 119.6(2) . . ? C14 C13 Br24 118.9(2) . . ? C15 C14 C13 119.1(3) . . ? C14 C15 C10 120.4(3) . . ? C1 C16 C17 123.1(3) . . ? C1 C16 C18 122.1(3) . . ? C17 C16 C18 114.7(3) . . ? N20 C17 C16 176.8(5) . . ? N19 C18 C16 179.4(4) . . ? C5 N21 C22 120.2(3) . . ? C5 N21 C23 120.6(3) . . ? C22 N21 C23 115.9(3) . . ? C4 C3 H3 117.9 . . ? C2 C3 H3 120.1 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 118.9 . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 120.3 . . ? C6 C7 H7 117.7 . . ? C2 C7 H7 120.2 . . ? C9 C8 H8 116.3 . . ? C1 C8 H8 119.5 . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 113.7 . . ? C12 C11 H11 117.9 . . ? C10 C11 H11 121.1 . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 119.9 . . ? C15 C14 H14 121.0 . . ? C13 C14 H14 119.8 . . ? C14 C15 H15 119.1 . . ? C10 C15 H15 120.5 . . ? N21 C22 H22A 109.7 . . ? N21 C22 H22B 109.8 . . ? H22A C22 H22B 109.5 . . ? N21 C22 H22C 108.9 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N21 C23 H23A 110.1 . . ? N21 C23 H23B 109.6 . . ? H23A C23 H23B 109.5 . . ? N21 C23 H23C 108.7 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 C16 C1 C2 C3 134.6(3) . . . . ? C8 C1 C2 C3 -47.2(4) . . . . ? C16 C1 C2 C7 -45.2(4) . . . . ? C8 C1 C2 C7 133.1(3) . . . . ? C7 C2 C3 C4 2.1(4) . . . . ? C1 C2 C3 C4 -177.7(3) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C3 C4 C5 N21 179.4(3) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? N21 C5 C6 C7 -178.2(3) . . . . ? C4 C5 C6 C7 2.4(4) . . . . ? C5 C6 C7 C2 -1.4(5) . . . . ? C3 C2 C7 C6 -0.8(4) . . . . ? C1 C2 C7 C6 178.9(3) . . . . ? C16 C1 C8 C9 168.6(3) . . . . ? C2 C1 C8 C9 -9.6(5) . . . . ? C1 C8 C9 C10 -179.7(3) . . . . ? C8 C9 C10 C11 -174.4(3) . . . . ? C8 C9 C10 C15 6.3(5) . . . . ? C15 C10 C11 C12 1.2(5) . . . . ? C9 C10 C11 C12 -178.1(3) . . . . ? C10 C11 C12 C13 -1.3(5) . . . . ? C11 C12 C13 C14 0.7(5) . . . . ? C11 C12 C13 Br24 178.6(2) . . . . ? C12 C13 C14 C15 -0.1(5) . . . . ? Br24 C13 C14 C15 -178.0(3) . . . . ? C13 C14 C15 C10 0.0(5) . . . . ? C11 C10 C15 C14 -0.6(5) . . . . ? C9 C10 C15 C14 178.7(3) . . . . ? C8 C1 C16 C17 169.7(3) . . . . ? C2 C1 C16 C17 -12.0(5) . . . . ? C8 C1 C16 C18 -6.5(5) . . . . ? C2 C1 C16 C18 171.8(3) . . . . ? C1 C16 C17 N20 -117(7) . . . . ? C18 C16 C17 N20 59(8) . . . . ? C1 C16 C18 N19 16E1(5) . . . . ? C17 C16 C18 N19 -1E1(5) . . . . ? C6 C5 N21 C22 166.6(3) . . . . ? C4 C5 N21 C22 -14.0(5) . . . . ? C6 C5 N21 C23 7.7(5) . . . . ? C4 C5 N21 C23 -172.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.893 _diffrn_measured_fraction_theta_full 0.893 _refine_diff_density_max 0.409 _refine_diff_density_min -0.548 _refine_diff_density_rms 0.058 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ; _chemical_name_common ;(E)-2-(3-(4-bromophenyl)-1-(4- (dimethylamino)phenyl)allylidene)malononitrile ; data_3g _database_code_depnum_ccdc_archive 'CCDC 699251' _chemical_compound_source 'LOC ETH Zurich' _exptl_crystal_description plate _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .006 _exptl_crystal_F_000 696.0 _exptl_crystal_colour Cinnabar _cell_measurement_temperature 203 _refine_ls_hydrogen_treatment refall _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.09883 _diffrn_orient_matrix_UB_12 0.04275 _diffrn_orient_matrix_UB_13 0.07743 _diffrn_orient_matrix_UB_21 -0.00857 _diffrn_orient_matrix_UB_22 -0.03408 _diffrn_orient_matrix_UB_23 0.06196 _diffrn_orient_matrix_UB_31 0.03460 _diffrn_orient_matrix_UB_32 -0.05429 _diffrn_orient_matrix_UB_33 -0.00540 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 329.403 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z _symmetry_space_group_name_H-M 'P -1 ' _symmetry_cell_setting Triclinic _chemical_formula_moiety 'C21 H19 N3 O ' _chemical_formula_sum 'C21 H19 N3 O ' _chemical_name_systematic ; 2-(1-(4-(dimethylamino)phenyl)-3-(4-methoxyphenyl)allylidene)propanedinitrile ; _cell_length_a 7.8176(2) _cell_length_b 15.0473(4) _cell_length_c 16.0532(5) _cell_angle_alpha 104.702(2) _cell_angle_beta 90.581(2) _cell_angle_gamma 104.638(2) _cell_volume 1761.71(9) _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_number 10655 _diffrn_reflns_theta_max 25.19 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_full 25.19 _cell_measurement_reflns_used 16543 _cell_measurement_theta_min 2.425 _cell_measurement_theta_max 25.028 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97(Altomare et al., J. Appl. Cryst.,1999)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_absorpt_coefficient_mu 0.078 _reflns_number_total 6111 _reflns_number_gt 4731 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.034(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6111 _refine_ls_number_parameters 604 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _refine_ls_shift/su_max 0.002 _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 O11 O 0.22312(19) 0.92393(10) 0.93357(10) 0.0538(4) Uani 1 1 d . . . O36 O 0.71457(19) 0.91862(10) 0.77344(9) 0.0520(4) Uani 1 1 d . . . N19 N -0.3336(2) 0.13079(11) 0.61061(10) 0.0474(4) Uani 1 1 d . . . N23 N -0.5630(2) 0.20331(13) 1.00297(11) 0.0520(4) Uani 1 1 d . . . N25 N -0.3597(3) 0.49646(13) 1.15168(11) 0.0572(5) Uani 1 1 d . . . N44 N 0.1719(2) 0.13078(11) 0.71277(10) 0.0467(4) Uani 1 1 d . . . N48 N -0.0698(2) 0.19885(13) 0.34938(12) 0.0555(5) Uani 1 1 d . . . N50 N 0.1346(3) 0.49234(13) 0.34256(11) 0.0557(5) Uani 1 1 d . . . C1 C -0.3828(2) 0.37288(13) 1.00451(11) 0.0383(4) Uani 1 1 d . . . C2 C -0.3085(2) 0.40000(13) 0.93404(11) 0.0370(4) Uani 1 1 d . . . C3 C -0.2260(2) 0.50010(13) 0.94320(12) 0.0397(4) Uani 1 1 d . . . C4 C -0.1144(2) 0.53604(13) 0.88974(12) 0.0388(4) Uani 1 1 d . . . C5 C -0.0306(2) 0.63646(13) 0.89977(11) 0.0370(4) Uani 1 1 d . . . C6 C -0.0714(3) 0.70942(13) 0.96343(12) 0.0421(4) Uani 1 1 d . . . C7 C 0.0132(3) 0.80341(14) 0.97184(12) 0.0444(4) Uani 1 1 d . . . C8 C 0.1453(2) 0.82846(13) 0.91791(12) 0.0409(4) Uani 1 1 d . . . C9 C 0.1855(2) 0.75797(14) 0.85287(12) 0.0417(4) Uani 1 1 d . . . C10 C 0.0976(2) 0.66382(14) 0.84405(12) 0.0411(4) Uani 1 1 d . . . C12 C 0.3728(3) 0.95162(18) 0.88642(18) 0.0598(6) Uani 1 1 d . . . C13 C -0.3147(2) 0.32924(12) 0.85122(11) 0.0349(4) Uani 1 1 d . . . C14 C -0.3535(2) 0.34906(13) 0.77349(11) 0.0380(4) Uani 1 1 d . . . C15 C -0.3607(2) 0.28376(13) 0.69515(11) 0.0393(4) Uani 1 1 d . . . C16 C -0.3279(2) 0.19534(12) 0.68965(11) 0.0370(4) Uani 1 1 d . . . C17 C -0.2912(2) 0.17456(13) 0.76786(12) 0.0392(4) Uani 1 1 d . . . C18 C -0.2843(2) 0.24033(13) 0.84595(12) 0.0383(4) Uani 1 1 d . . . C20 C -0.3122(3) 0.16522(18) 0.53401(13) 0.0528(5) Uani 1 1 d . . . C21 C -0.2892(4) 0.04234(16) 0.60594(16) 0.0561(5) Uani 1 1 d . . . C22 C -0.4808(2) 0.27814(14) 1.00218(11) 0.0405(4) Uani 1 1 d . . . C24 C -0.3695(3) 0.44129(14) 1.08640(12) 0.0433(4) Uani 1 1 d . . . C26 C 0.1104(2) 0.36844(13) 0.43050(11) 0.0378(4) Uani 1 1 d . . . C27 C 0.1843(2) 0.39546(12) 0.51449(11) 0.0358(4) Uani 1 1 d . . . C28 C 0.2681(2) 0.49575(13) 0.55361(12) 0.0393(4) Uani 1 1 d . . . C29 C 0.3820(2) 0.53115(13) 0.62381(12) 0.0377(4) Uani 1 1 d . . . C30 C 0.4667(2) 0.63157(12) 0.66312(11) 0.0363(4) Uani 1 1 d . . . C31 C 0.5888(2) 0.65801(13) 0.73433(12) 0.0400(4) Uani 1 1 d . . . C32 C 0.6757(2) 0.75233(14) 0.77316(12) 0.0417(4) Uani 1 1 d . . . C33 C 0.6381(2) 0.82313(13) 0.74083(12) 0.0396(4) Uani 1 1 d . . . C34 C 0.5131(3) 0.79879(14) 0.67099(12) 0.0444(4) Uani 1 1 d . . . C35 C 0.4301(3) 0.70503(13) 0.63256(12) 0.0422(4) Uani 1 1 d . . . C37 C 0.8465(4) 0.94612(19) 0.84349(18) 0.0661(7) Uani 1 1 d . . . C38 C 0.1791(2) 0.32574(12) 0.56415(11) 0.0351(4) Uani 1 1 d . . . C39 C 0.2082(2) 0.23632(13) 0.52766(12) 0.0388(4) Uani 1 1 d . . . C40 C 0.2045(2) 0.17217(13) 0.57589(12) 0.0402(4) Uani 1 1 d . . . C41 C 0.1730(2) 0.19418(12) 0.66381(11) 0.0368(4) Uani 1 1 d . . . C42 C 0.1405(2) 0.28297(13) 0.70004(12) 0.0381(4) Uani 1 1 d . . . C43 C 0.1437(2) 0.34668(13) 0.65159(11) 0.0377(4) Uani 1 1 d . . . C45 C 0.2045(3) 0.03942(16) 0.67415(17) 0.0559(6) Uani 1 1 d . . . C46 C 0.1968(3) 0.16584(18) 0.80580(14) 0.0532(5) Uani 1 1 d . . . C47 C 0.0117(3) 0.27337(14) 0.38657(12) 0.0416(4) Uani 1 1 d . . . C49 C 0.1239(3) 0.43681(13) 0.38109(12) 0.0418(4) Uani 1 1 d . . . H29 H 0.416(3) 0.4894(15) 0.6545(12) 0.044(5) Uiso 1 1 d . . . H39 H 0.237(3) 0.2217(14) 0.4673(13) 0.043(5) Uiso 1 1 d . . . H31 H 0.609(3) 0.6082(15) 0.7560(13) 0.050(6) Uiso 1 1 d . . . H18 H -0.251(3) 0.2252(14) 0.8992(13) 0.043(5) Uiso 1 1 d . . . H4 H -0.085(3) 0.4905(15) 0.8404(14) 0.049(5) Uiso 1 1 d . . . H6 H -0.161(3) 0.6934(14) 1.0036(13) 0.042(5) Uiso 1 1 d . . . H15 H -0.390(2) 0.3014(13) 0.6426(12) 0.037(5) Uiso 1 1 d . . . H42 H 0.118(3) 0.3007(14) 0.7594(13) 0.043(5) Uiso 1 1 d . . . H43 H 0.116(2) 0.4060(15) 0.6794(12) 0.040(5) Uiso 1 1 d . . . H14 H -0.387(3) 0.4089(15) 0.7744(12) 0.043(5) Uiso 1 1 d . . . H28 H 0.240(3) 0.5369(15) 0.5207(13) 0.047(5) Uiso 1 1 d . . . H10 H 0.126(2) 0.6130(14) 0.7988(12) 0.036(5) Uiso 1 1 d . . . H3 H -0.248(3) 0.5443(16) 0.9965(14) 0.053(6) Uiso 1 1 d . . . H35 H 0.347(3) 0.6904(15) 0.5805(15) 0.054(6) Uiso 1 1 d . . . H32 H 0.758(3) 0.7682(14) 0.8238(13) 0.041(5) Uiso 1 1 d . . . H46 H 0.208(3) 0.1141(19) 0.8313(16) 0.073(7) Uiso 1 1 d . . . H34 H 0.490(3) 0.8507(18) 0.6470(15) 0.068(7) Uiso 1 1 d . . . H20 H -0.209(4) 0.220(2) 0.5416(17) 0.083(8) Uiso 1 1 d . . . H7 H -0.021(3) 0.8571(17) 1.0162(16) 0.064(6) Uiso 1 1 d . . . H17 H -0.270(2) 0.1136(14) 0.7669(12) 0.037(5) Uiso 1 1 d . . . H40 H 0.225(3) 0.1090(16) 0.5475(14) 0.050(5) Uiso 1 1 d . . . H20B H -0.418(4) 0.1889(18) 0.5177(16) 0.070(7) Uiso 1 1 d . . . H45A H 0.125(4) 0.004(2) 0.6187(19) 0.079(8) Uiso 1 1 d . . . H46B H 0.090(3) 0.1868(17) 0.8310(15) 0.065(7) Uiso 1 1 d . . . H9 H 0.271(3) 0.7751(15) 0.8138(14) 0.052(6) Uiso 1 1 d . . . H20C H -0.301(4) 0.114(2) 0.4840(19) 0.081(8) Uiso 1 1 d . . . H37A H 0.804(4) 0.929(2) 0.8953(18) 0.077(8) Uiso 1 1 d . . . H12A H 0.409(3) 1.0205(18) 0.9075(15) 0.060(6) Uiso 1 1 d . . . H21A H -0.341(4) -0.0019(19) 0.5480(18) 0.076(7) Uiso 1 1 d . . . H21B H -0.355(4) 0.009(2) 0.6487(18) 0.083(8) Uiso 1 1 d . . . H12B H 0.345(4) 0.9358(19) 0.8231(19) 0.081(8) Uiso 1 1 d . . . H46C H 0.285(4) 0.2284(19) 0.8250(16) 0.070(7) Uiso 1 1 d . . . H45B H 0.183(4) 0.003(2) 0.714(2) 0.096(9) Uiso 1 1 d . . . H12C H 0.465(3) 0.9186(18) 0.8957(16) 0.068(7) Uiso 1 1 d . . . H37B H 0.884(4) 1.017(2) 0.8570(18) 0.088(8) Uiso 1 1 d . . . H45C H 0.333(4) 0.0464(18) 0.6572(16) 0.072(7) Uiso 1 1 d . . . H37C H 0.950(4) 0.919(2) 0.824(2) 0.098(10) Uiso 1 1 d . . . H21C H -0.163(5) 0.045(2) 0.614(2) 0.099(10) 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 O11 0.0545(8) 0.0388(8) 0.0605(9) 0.0084(6) 0.0049(7) 0.0034(6) O36 0.0574(8) 0.0368(7) 0.0522(8) 0.0101(6) -0.0092(6) -0.0025(6) N19 0.0620(10) 0.0397(9) 0.0356(9) 0.0029(7) 0.0066(7) 0.0114(8) N23 0.0576(10) 0.0475(11) 0.0481(10) 0.0132(8) 0.0072(8) 0.0082(8) N25 0.0764(13) 0.0519(11) 0.0406(10) 0.0045(9) 0.0087(9) 0.0198(9) N44 0.0604(10) 0.0386(9) 0.0443(9) 0.0157(7) 0.0039(7) 0.0139(7) N48 0.0637(11) 0.0420(10) 0.0518(10) 0.0065(8) -0.0076(8) 0.0045(9) N50 0.0748(12) 0.0473(10) 0.0489(10) 0.0197(9) 0.0042(9) 0.0158(9) C1 0.0431(10) 0.0388(10) 0.0325(9) 0.0072(7) 0.0007(7) 0.0121(8) C2 0.0376(9) 0.0389(10) 0.0340(9) 0.0081(8) -0.0012(7) 0.0110(7) C3 0.0462(10) 0.0373(10) 0.0321(9) 0.0035(8) -0.0011(8) 0.0106(8) C4 0.0394(9) 0.0383(10) 0.0357(10) 0.0051(8) -0.0029(8) 0.0097(8) C5 0.0383(9) 0.0379(10) 0.0323(9) 0.0064(7) -0.0028(7) 0.0085(8) C6 0.0450(10) 0.0406(10) 0.0374(10) 0.0069(8) 0.0038(8) 0.0088(8) C7 0.0495(11) 0.0393(11) 0.0393(10) 0.0025(8) 0.0014(8) 0.0106(9) C8 0.0433(10) 0.0364(10) 0.0402(10) 0.0091(8) -0.0051(8) 0.0072(8) C9 0.0409(10) 0.0441(11) 0.0382(10) 0.0110(8) 0.0012(8) 0.0080(8) C10 0.0460(10) 0.0412(11) 0.0341(9) 0.0055(8) 0.0002(8) 0.0126(8) C12 0.0627(14) 0.0439(13) 0.0699(16) 0.0194(12) 0.0090(12) 0.0043(11) C13 0.0374(9) 0.0348(9) 0.0318(9) 0.0092(7) 0.0017(7) 0.0078(7) C14 0.0452(10) 0.0316(9) 0.0365(10) 0.0095(8) -0.0011(8) 0.0084(8) C15 0.0468(10) 0.0359(10) 0.0327(9) 0.0105(8) -0.0012(8) 0.0053(8) C16 0.0360(9) 0.0359(10) 0.0352(9) 0.0070(7) 0.0042(7) 0.0046(7) C17 0.0432(10) 0.0356(10) 0.0401(10) 0.0110(8) 0.0044(8) 0.0119(8) C18 0.0425(10) 0.0395(10) 0.0348(9) 0.0119(8) 0.0028(7) 0.0125(8) C20 0.0597(13) 0.0589(14) 0.0324(10) 0.0050(10) 0.0073(9) 0.0091(11) C21 0.0659(15) 0.0425(12) 0.0526(13) -0.0022(10) 0.0049(11) 0.0165(10) C22 0.0439(10) 0.0465(11) 0.0312(9) 0.0092(8) 0.0040(7) 0.0133(9) C24 0.0504(11) 0.0441(11) 0.0365(10) 0.0115(9) 0.0057(8) 0.0138(8) C26 0.0419(9) 0.0350(10) 0.0360(9) 0.0102(8) 0.0053(7) 0.0083(8) C27 0.0364(9) 0.0354(9) 0.0359(9) 0.0101(7) 0.0074(7) 0.0092(7) C28 0.0460(10) 0.0348(9) 0.0382(10) 0.0135(8) 0.0063(8) 0.0084(8) C29 0.0393(9) 0.0338(10) 0.0407(10) 0.0136(8) 0.0057(8) 0.0070(8) C30 0.0391(9) 0.0351(10) 0.0349(9) 0.0117(8) 0.0063(7) 0.0076(7) C31 0.0438(10) 0.0392(10) 0.0395(10) 0.0149(8) 0.0064(8) 0.0108(8) C32 0.0393(10) 0.0452(11) 0.0378(10) 0.0117(8) -0.0006(8) 0.0058(8) C33 0.0431(10) 0.0327(9) 0.0380(10) 0.0091(8) 0.0049(8) 0.0016(8) C34 0.0519(11) 0.0353(10) 0.0443(11) 0.0140(8) -0.0021(8) 0.0052(8) C35 0.0472(10) 0.0377(10) 0.0385(10) 0.0110(8) -0.0036(8) 0.0049(8) C37 0.0706(16) 0.0467(14) 0.0639(16) 0.0097(12) -0.0220(13) -0.0087(12) C38 0.0371(9) 0.0311(9) 0.0344(9) 0.0066(7) 0.0046(7) 0.0064(7) C39 0.0435(10) 0.0388(10) 0.0339(10) 0.0072(8) 0.0062(8) 0.0129(8) C40 0.0483(10) 0.0321(10) 0.0398(10) 0.0059(8) 0.0049(8) 0.0134(8) C41 0.0374(9) 0.0320(9) 0.0387(10) 0.0104(7) 0.0016(7) 0.0041(7) C42 0.0447(10) 0.0341(9) 0.0318(9) 0.0063(7) 0.0056(8) 0.0059(8) C43 0.0419(10) 0.0308(9) 0.0367(10) 0.0051(7) 0.0056(7) 0.0068(8) C45 0.0664(14) 0.0428(12) 0.0667(15) 0.0233(11) 0.0072(12) 0.0204(11) C46 0.0604(13) 0.0548(14) 0.0437(12) 0.0222(10) -0.0015(10) 0.0052(11) C47 0.0469(10) 0.0426(11) 0.0356(10) 0.0115(9) 0.0038(8) 0.0110(9) C49 0.0481(10) 0.0401(10) 0.0355(9) 0.0084(8) 0.0034(8) 0.0103(8) _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 O11 C8 1.367(2) . ? O11 C12 1.431(3) . ? O36 C33 1.369(2) . ? O36 C37 1.423(3) . ? N19 C16 1.381(2) . ? N19 C21 1.442(3) . ? N19 C20 1.446(3) . ? N23 C22 1.150(2) . ? N25 C24 1.148(2) . ? N44 C41 1.380(2) . ? N44 C45 1.445(3) . ? N44 C46 1.445(3) . ? N48 C47 1.145(2) . ? N50 C49 1.147(2) . ? C1 C2 1.383(2) . ? C1 C22 1.429(3) . ? C1 C24 1.434(3) . ? C2 C3 1.450(3) . ? C2 C13 1.469(2) . ? C3 C4 1.343(3) . ? C4 C5 1.453(3) . ? C5 C6 1.402(3) . ? C5 C10 1.404(2) . ? C6 C7 1.373(3) . ? C7 C8 1.395(3) . ? C8 C9 1.388(3) . ? C9 C10 1.380(3) . ? C13 C18 1.399(3) . ? C13 C14 1.402(2) . ? C14 C15 1.376(3) . ? C15 C16 1.399(3) . ? C16 C17 1.412(3) . ? C17 C18 1.377(3) . ? C26 C27 1.380(3) . ? C26 C47 1.435(3) . ? C26 C49 1.435(2) . ? C27 C28 1.453(3) . ? C27 C38 1.463(2) . ? C28 C29 1.335(3) . ? C29 C30 1.457(3) . ? C30 C31 1.389(3) . ? C30 C35 1.406(3) . ? C31 C32 1.385(3) . ? C32 C33 1.388(3) . ? C33 C34 1.391(3) . ? C34 C35 1.371(3) . ? C38 C39 1.401(2) . ? C38 C43 1.405(2) . ? C39 C40 1.378(3) . ? C40 C41 1.405(3) . ? C41 C42 1.403(3) . ? C42 C43 1.375(3) . ? C3 H3 0.99(2) . ? C4 H4 0.98(2) . ? C6 H6 0.98(2) . ? C7 H7 1.03(2) . ? C9 H9 0.96(2) . ? C10 H10 0.986(19) . ? C12 H12A 0.97(3) . ? C12 H12B 0.99(3) . ? C12 H12C 1.00(3) . ? C14 H14 1.00(2) . ? C15 H15 0.989(19) . ? C17 H17 0.97(2) . ? C18 H18 0.99(2) . ? C20 H20 0.98(3) . ? C20 H20B 1.04(3) . ? C20 H20C 0.98(3) . ? C21 H21A 1.01(3) . ? C21 H21B 1.02(3) . ? C21 H21C 0.98(3) . ? C28 H28 0.97(2) . ? C29 H29 0.97(2) . ? C31 H31 0.95(2) . ? C32 H32 0.97(2) . ? C34 H34 1.01(2) . ? C35 H35 1.00(2) . ? C37 H37A 0.97(3) . ? C37 H37B 1.00(3) . ? C37 H37C 1.01(3) . ? C39 H39 0.98(2) . ? C40 H40 1.00(2) . ? C42 H42 0.95(2) . ? C43 H43 0.97(2) . ? C45 H45A 1.02(3) . ? C45 H45B 0.94(3) . ? C45 H45C 1.03(3) . ? C46 H46 0.99(3) . ? C46 H46B 1.02(3) . ? C46 H46C 0.99(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 C8 O11 C12 116.82(16) . . ? C33 O36 C37 117.04(17) . . ? C16 N19 C21 120.13(17) . . ? C16 N19 C20 118.79(17) . . ? C21 N19 C20 116.46(17) . . ? C41 N44 C45 120.20(17) . . ? C41 N44 C46 119.16(17) . . ? C45 N44 C46 117.57(18) . . ? C2 C1 C22 124.20(17) . . ? C2 C1 C24 120.83(17) . . ? C22 C1 C24 114.95(15) . . ? C1 C2 C3 118.59(16) . . ? C1 C2 C13 120.87(16) . . ? C3 C2 C13 120.53(15) . . ? C4 C3 C2 125.96(17) . . ? C3 C4 C5 125.71(17) . . ? C6 C5 C10 117.13(17) . . ? C6 C5 C4 123.06(16) . . ? C10 C5 C4 119.81(16) . . ? C7 C6 C5 121.28(17) . . ? C6 C7 C8 120.42(18) . . ? O11 C8 C9 125.13(16) . . ? O11 C8 C7 115.26(16) . . ? C9 C8 C7 119.59(17) . . ? C10 C9 C8 119.47(17) . . ? C9 C10 C5 122.01(17) . . ? C18 C13 C14 117.33(16) . . ? C18 C13 C2 122.44(15) . . ? C14 C13 C2 120.23(16) . . ? C15 C14 C13 121.29(17) . . ? C14 C15 C16 121.47(17) . . ? N19 C16 C15 120.96(16) . . ? N19 C16 C17 121.62(17) . . ? C15 C16 C17 117.41(16) . . ? C18 C17 C16 120.69(17) . . ? C17 C18 C13 121.79(17) . . ? N23 C22 C1 177.36(19) . . ? N25 C24 C1 179.4(2) . . ? C27 C26 C47 124.22(15) . . ? C27 C26 C49 120.93(17) . . ? C47 C26 C49 114.82(16) . . ? C26 C27 C28 118.52(15) . . ? C26 C27 C38 121.48(16) . . ? C28 C27 C38 120.00(16) . . ? C29 C28 C27 125.89(17) . . ? C28 C29 C30 126.10(17) . . ? C31 C30 C35 117.27(17) . . ? C31 C30 C29 119.86(16) . . ? C35 C30 C29 122.87(17) . . ? C32 C31 C30 122.23(17) . . ? C31 C32 C33 119.09(18) . . ? O36 C33 C32 124.70(17) . . ? O36 C33 C34 115.43(16) . . ? C32 C33 C34 119.86(17) . . ? C35 C34 C33 120.31(18) . . ? C34 C35 C30 121.21(18) . . ? C39 C38 C43 117.21(15) . . ? C39 C38 C27 122.32(15) . . ? C43 C38 C27 120.47(15) . . ? C40 C39 C38 121.32(17) . . ? C39 C40 C41 121.31(17) . . ? N44 C41 C42 121.01(16) . . ? N44 C41 C40 121.55(16) . . ? C42 C41 C40 117.44(15) . . ? C43 C42 C41 121.05(16) . . ? C42 C43 C38 121.64(17) . . ? N48 C47 C26 177.4(2) . . ? N50 C49 C26 179.1(2) . . ? C4 C3 H3 118.3(12) . . ? C2 C3 H3 115.6(12) . . ? C3 C4 H4 117.0(12) . . ? C5 C4 H4 117.3(12) . . ? C7 C6 H6 118.9(11) . . ? C5 C6 H6 119.8(11) . . ? C6 C7 H7 121.4(13) . . ? C8 C7 H7 118.1(13) . . ? C10 C9 H9 120.7(13) . . ? C8 C9 H9 119.8(13) . . ? C9 C10 H10 120.3(10) . . ? C5 C10 H10 117.6(11) . . ? O11 C12 H12A 103.8(13) . . ? O11 C12 H12B 114.0(16) . . ? H12A C12 H12B 107(2) . . ? O11 C12 H12C 109.8(14) . . ? H12A C12 H12C 115(2) . . ? H12B C12 H12C 107(2) . . ? C15 C14 H14 118.5(11) . . ? C13 C14 H14 120.0(11) . . ? C14 C15 H15 117.6(11) . . ? C16 C15 H15 120.9(11) . . ? C18 C17 H17 119.4(11) . . ? C16 C17 H17 119.9(11) . . ? C17 C18 H18 118.6(12) . . ? C13 C18 H18 119.5(12) . . ? N19 C20 H20 111.7(16) . . ? N19 C20 H20B 113.5(13) . . ? H20 C20 H20B 105(2) . . ? N19 C20 H20C 110.4(16) . . ? H20 C20 H20C 110(2) . . ? H20B C20 H20C 106(2) . . ? N19 C21 H21A 106.6(15) . . ? N19 C21 H21B 110.7(15) . . ? H21A C21 H21B 104(2) . . ? N19 C21 H21C 117.7(18) . . ? H21A C21 H21C 110(2) . . ? H21B C21 H21C 108(2) . . ? C29 C28 H28 121.0(13) . . ? C27 C28 H28 113.0(13) . . ? C28 C29 H29 120.9(12) . . ? C30 C29 H29 113.0(12) . . ? C32 C31 H31 121.0(13) . . ? C30 C31 H31 116.7(13) . . ? C31 C32 H32 119.9(12) . . ? C33 C32 H32 121.0(12) . . ? C35 C34 H34 120.5(15) . . ? C33 C34 H34 119.1(15) . . ? C34 C35 H35 117.8(12) . . ? C30 C35 H35 120.9(12) . . ? O36 C37 H37A 114.4(17) . . ? O36 C37 H37B 104.1(17) . . ? H37A C37 H37B 108(2) . . ? O36 C37 H37C 109.5(19) . . ? H37A C37 H37C 111(2) . . ? H37B C37 H37C 110(2) . . ? C40 C39 H39 120.6(11) . . ? C38 C39 H39 118.1(11) . . ? C39 C40 H40 118.9(12) . . ? C41 C40 H40 119.8(12) . . ? C43 C42 H42 118.8(12) . . ? C41 C42 H42 120.2(12) . . ? C42 C43 H43 117.5(11) . . ? C38 C43 H43 120.8(11) . . ? N44 C45 H45A 111.5(15) . . ? N44 C45 H45B 108.2(19) . . ? H45A C45 H45B 110(2) . . ? N44 C45 H45C 111.8(14) . . ? H45A C45 H45C 106(2) . . ? H45B C45 H45C 109(2) . . ? N44 C46 H46 109.7(15) . . ? N44 C46 H46B 111.6(14) . . ? H46 C46 H46B 105.9(19) . . ? N44 C46 H46C 112.4(14) . . ? H46 C46 H46C 119(2) . . ? H46B C46 H46C 97.6(19) . . ? 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 C22 C1 C2 C3 174.54(17) . . . . ? C24 C1 C2 C3 -3.7(3) . . . . ? C22 C1 C2 C13 -4.7(3) . . . . ? C24 C1 C2 C13 177.07(16) . . . . ? C1 C2 C3 C4 163.72(18) . . . . ? C13 C2 C3 C4 -17.0(3) . . . . ? C2 C3 C4 C5 -179.32(17) . . . . ? C3 C4 C5 C6 -6.5(3) . . . . ? C3 C4 C5 C10 173.51(18) . . . . ? C10 C5 C6 C7 -1.3(3) . . . . ? C4 C5 C6 C7 178.73(17) . . . . ? C5 C6 C7 C8 -1.3(3) . . . . ? C12 O11 C8 C9 -8.5(3) . . . . ? C12 O11 C8 C7 172.94(19) . . . . ? C6 C7 C8 O11 -178.49(17) . . . . ? C6 C7 C8 C9 2.9(3) . . . . ? O11 C8 C9 C10 179.75(17) . . . . ? C7 C8 C9 C10 -1.8(3) . . . . ? C8 C9 C10 C5 -0.9(3) . . . . ? C6 C5 C10 C9 2.4(3) . . . . ? C4 C5 C10 C9 -177.60(17) . . . . ? C1 C2 C13 C18 -41.8(3) . . . . ? C3 C2 C13 C18 138.96(18) . . . . ? C1 C2 C13 C14 137.69(18) . . . . ? C3 C2 C13 C14 -41.6(2) . . . . ? C18 C13 C14 C15 -0.2(3) . . . . ? C2 C13 C14 C15 -179.72(16) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C21 N19 C16 C15 176.35(19) . . . . ? C20 N19 C16 C15 21.3(3) . . . . ? C21 N19 C16 C17 -4.5(3) . . . . ? C20 N19 C16 C17 -159.52(18) . . . . ? C14 C15 C16 N19 -179.27(16) . . . . ? C14 C15 C16 C17 1.5(3) . . . . ? N19 C16 C17 C18 179.31(17) . . . . ? C15 C16 C17 C18 -1.5(3) . . . . ? C16 C17 C18 C13 0.6(3) . . . . ? C14 C13 C18 C17 0.2(3) . . . . ? C2 C13 C18 C17 179.73(16) . . . . ? C2 C1 C22 N23 -155(4) . . . . ? C24 C1 C22 N23 23(5) . . . . ? C2 C1 C24 N25 6E1(3) . . . . ? C22 C1 C24 N25 -12E1(3) . . . . ? C47 C26 C27 C28 -174.83(16) . . . . ? C49 C26 C27 C28 3.3(3) . . . . ? C47 C26 C27 C38 4.9(3) . . . . ? C49 C26 C27 C38 -176.95(15) . . . . ? C26 C27 C28 C29 -162.14(18) . . . . ? C38 C27 C28 C29 18.1(3) . . . . ? C27 C28 C29 C30 179.80(15) . . . . ? C28 C29 C30 C31 -177.31(17) . . . . ? C28 C29 C30 C35 3.1(3) . . . . ? C35 C30 C31 C32 -1.7(2) . . . . ? C29 C30 C31 C32 178.73(15) . . . . ? C30 C31 C32 C33 0.9(3) . . . . ? C37 O36 C33 C32 2.4(3) . . . . ? C37 O36 C33 C34 -178.4(2) . . . . ? C31 C32 C33 O36 179.90(16) . . . . ? C31 C32 C33 C34 0.7(3) . . . . ? O36 C33 C34 C35 179.13(16) . . . . ? C32 C33 C34 C35 -1.6(3) . . . . ? C33 C34 C35 C30 0.9(3) . . . . ? C31 C30 C35 C34 0.7(3) . . . . ? C29 C30 C35 C34 -179.67(16) . . . . ? C26 C27 C38 C39 41.0(3) . . . . ? C28 C27 C38 C39 -139.22(18) . . . . ? C26 C27 C38 C43 -138.87(18) . . . . ? C28 C27 C38 C43 40.9(2) . . . . ? C43 C38 C39 C40 -0.8(3) . . . . ? C27 C38 C39 C40 179.31(17) . . . . ? C38 C39 C40 C41 -0.6(3) . . . . ? C45 N44 C41 C42 179.61(19) . . . . ? C46 N44 C41 C42 -20.7(3) . . . . ? C45 N44 C41 C40 0.3(3) . . . . ? C46 N44 C41 C40 160.02(19) . . . . ? C39 C40 C41 N44 -178.95(18) . . . . ? C39 C40 C41 C42 1.7(3) . . . . ? N44 C41 C42 C43 179.17(17) . . . . ? C40 C41 C42 C43 -1.5(3) . . . . ? C41 C42 C43 C38 0.1(3) . . . . ? C39 C38 C43 C42 1.0(3) . . . . ? C27 C38 C43 C42 -179.08(17) . . . . ? C27 C26 C47 N48 160(4) . . . . ? C49 C26 C47 N48 -18(5) . . . . ? C27 C26 C49 N50 -35(14) . . . . ? C47 C26 C49 N50 144(14) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.152 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.044 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ; _chemical_name_common ;2-(1-(4-(dimethylamino)phenyl)-3-(4- methoxyphenyl)allylidene)propanedinitrile ;