data_global _journal_coden_Cambridge 188 loop_ _publ_author_name _publ_author_address 'Freier, Thomas' ; Institut fur Organische Katalyseforschung an der Universitat Rostock Buchbinderstr. 5/6 D-18055 Rostock Bundesrepublik Deutschland ; 'Michalik, Manfred' ; Institut fur Organische Katalyseforschung an der Universitat Rostock Buchbinderstr. 5/6 D-18055 Rostock Bundesrepublik Deutschland ; 'Peseke, Klaus' ; Fachbereich Chemie Universitat Rostock Buchbinderstr. 9 D-18051 Rostock Bundesrepublik Deutschland ; 'Reinke, Helmut' ; Fachbereich Chemie Universitat Rostock Buchbinderstr. 9 D-18051 Rostock Bundesrepublik Deutschland ; #====================================================================== # 1. SUBMISSION DETAILS _publ_contact_author_name 'Prof Manfred Michalik' _publ_contact_author_address ; Institut fur Organische Katalysforshung an der Universiata Rostock Buchbinderstr. 5-6 Rostock D-18055 GERMANY ; _publ_contact_author_phone '049 381 498 6370' _publ_contact_author_fax '049 381 498 6382' _publ_contact_author_email 'manfred.michalik@ifok.uni-rostock.de' _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 2' _publ_contact_letter ; The actual main author is: Prof. Dr. M. Michalik Institut fur Organische Katalyseforschung an der Universitat Rostock Buchbinderstr. 5/6 D-18055 Rostock Bundesrepublik Deutschland However, the x-ray investigations were performed by Prof.Dr. H. Reinke. Please make use of his address in questions of the x-ray analysis. ; #====================================================================== # 2. TITLE AND AUTHOR LIST _publ_section_title ; NMR studies on the axial chirality of ortho-substituted push-pull phenyl butadienes ; # The loop structure below should contain the names and addresses of # all authors, in the required order of publication. Repeat as # necessary. #====================================================================== data_f018(3h) _database_code_CSD 171037 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Cyano-3-(2-isopropylphenyl)-5,5-bis(methylthio)penta-2,4-dienenitrile ; _chemical_name_common ? _chemical_melting_point 361 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 S2' _chemical_formula_weight 314.45 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.466(2) _cell_length_b 11.727(2) _cell_length_c 17.473(3) _cell_angle_alpha 86.51(3) _cell_angle_beta 76.31(3) _cell_angle_gamma 67.13(3) _cell_volume 1735.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 5.833 _cell_measurement_theta_max 26.047 _exptl_crystal_description 'part of prism' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method '?' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3139 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3121 _reflns_number_gt 2728 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXTL, Version 4.2 for MSDOS' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.3862P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.035(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3121 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 S1 S 0.46634(12) 0.33272(10) 0.17127(5) 0.0759(4) Uani 1 1 d . . . S2 S 0.29832(11) 0.16945(9) 0.22383(5) 0.0674(3) Uani 1 1 d . . . N1 N 0.2337(4) 0.4350(3) -0.09731(14) 0.0654(9) Uani 1 1 d . . . N2 N -0.1252(4) 0.2878(4) -0.03979(17) 0.0849(13) Uani 1 1 d . . . C1 C 0.1758(4) 0.3815(3) -0.05267(15) 0.0458(8) Uani 1 1 d . . . C2 C 0.1038(3) 0.3129(3) 0.00233(15) 0.0435(8) Uani 1 1 d . . . C3 C 0.1502(3) 0.2723(3) 0.07075(14) 0.0395(8) Uani 1 1 d . . . C4 C 0.2639(3) 0.3080(3) 0.09226(14) 0.0425(8) Uani 1 1 d . . . H4A H 0.2940 0.3637 0.0591 0.051 Uiso 1 1 calc R . . C5 C 0.3352(4) 0.2730(3) 0.15389(14) 0.0468(8) Uani 1 1 d . . . C6 C -0.0246(4) 0.2966(4) -0.01929(17) 0.0564(11) Uani 1 1 d . . . C7 C 0.4627(5) 0.1186(5) 0.2684(2) 0.0878(14) Uani 1 1 d . . . H7A H 0.4512 0.0607 0.3083 0.132 Uiso 1 1 calc R . . H7B H 0.4674 0.1886 0.2920 0.132 Uiso 1 1 calc R . . H7C H 0.5581 0.0793 0.2291 0.132 Uiso 1 1 calc R . . C8 C 0.4851(5) 0.4338(4) 0.0921(2) 0.0890(14) Uani 1 1 d . . . H8A H 0.5568 0.4702 0.0984 0.133 Uiso 1 1 calc R . . H8B H 0.3838 0.4979 0.0926 0.133 Uiso 1 1 calc R . . H8C H 0.5247 0.3874 0.0429 0.133 Uiso 1 1 calc R . . C9 C 0.0721(4) 0.1965(3) 0.12254(15) 0.0423(8) Uani 1 1 d . . . C10 C 0.1343(4) 0.0671(3) 0.11279(16) 0.0512(9) Uani 1 1 d . . . C11 C 0.0522(4) 0.0048(3) 0.16340(19) 0.0684(11) Uani 1 1 d . . . H11A H 0.0883 -0.0809 0.1581 0.082 Uiso 1 1 calc R . . C12 C -0.0797(5) 0.0664(4) 0.2204(2) 0.0721(12) Uani 1 1 d . . . H12A H -0.1307 0.0218 0.2534 0.087 Uiso 1 1 calc R . . C13 C -0.1374(5) 0.1917(4) 0.22973(19) 0.0693(12) Uani 1 1 d . . . H13A H -0.2263 0.2328 0.2691 0.083 Uiso 1 1 calc R . . C14 C -0.0612(4) 0.2573(3) 0.17940(16) 0.0567(9) Uani 1 1 d . . . H14A H -0.1011 0.3432 0.1843 0.068 Uiso 1 1 calc R . . C15 C 0.2842(4) -0.0025(3) 0.05235(19) 0.0679(11) Uani 1 1 d . . . H15A H 0.3424 0.0520 0.0393 0.081 Uiso 1 1 calc R . . C16 C 0.2490(6) -0.0300(4) -0.0242(2) 0.0997(17) Uani 1 1 d . . . H16A H 0.3462 -0.0742 -0.0612 0.150 Uiso 1 1 calc R . . H16B H 0.1921 0.0464 -0.0461 0.150 Uiso 1 1 calc R . . H16C H 0.1866 -0.0795 -0.0131 0.150 Uiso 1 1 calc R . . C17 C 0.3903(5) -0.1191(4) 0.0833(3) 0.0953(14) Uani 1 1 d . . . H17A H 0.4105 -0.0996 0.1312 0.143 Uiso 1 1 calc R . . H17B H 0.4881 -0.1547 0.0449 0.143 Uiso 1 1 calc R . . H17C H 0.3399 -0.1772 0.0937 0.143 Uiso 1 1 calc R . . S1' S -0.26500(10) 0.80183(9) 0.33211(5) 0.0637(3) Uani 1 1 d . . . S2' S 0.07348(11) 0.65653(10) 0.27731(5) 0.0712(3) Uani 1 1 d . . . N1' N -0.1844(4) 0.9459(3) 0.60137(16) 0.0703(9) Uani 1 1 d . . . N2' N 0.3271(4) 0.8046(3) 0.55796(15) 0.0721(11) Uani 1 1 d . . . C1' C -0.0639(4) 0.8926(3) 0.56071(16) 0.0499(9) Uani 1 1 d . . . C2' C 0.0831(4) 0.8236(3) 0.50870(14) 0.0437(8) Uani 1 1 d . . . C3' C 0.0905(3) 0.7748(3) 0.43717(14) 0.0417(8) Uani 1 1 d . . . C4' C -0.0525(4) 0.8036(3) 0.41237(15) 0.0478(8) Uani 1 1 d . . . H4'A H -0.1422 0.8617 0.4440 0.057 Uiso 1 1 calc R . . C5' C -0.0756(4) 0.7576(3) 0.34849(15) 0.0486(8) Uani 1 1 d . . . C6' C 0.2212(4) 0.8099(3) 0.53479(16) 0.0520(10) Uani 1 1 d . . . C7' C -0.0227(5) 0.5947(5) 0.2255(2) 0.1054(18) Uani 1 1 d . . . H7'A H 0.0542 0.5374 0.1847 0.158 Uiso 1 1 calc R . . H7'B H -0.0961 0.6608 0.2023 0.158 Uiso 1 1 calc R . . H7'C H -0.0782 0.5526 0.2613 0.158 Uiso 1 1 calc R . . C8' C -0.3950(4) 0.8910(4) 0.4181(2) 0.0757(12) Uani 1 1 d . . . H8'A H -0.5018 0.9186 0.4129 0.114 Uiso 1 1 calc R . . H8'B H -0.3703 0.9615 0.4241 0.114 Uiso 1 1 calc R . . H8'C H -0.3827 0.8410 0.4635 0.114 Uiso 1 1 calc R . . C9' C 0.2462(4) 0.6965(3) 0.38865(14) 0.0428(8) Uani 1 1 d . . . C10' C 0.3121(4) 0.5684(3) 0.39827(15) 0.0449(8) Uani 1 1 d . . . C11' C 0.4571(4) 0.5012(3) 0.34996(17) 0.0568(9) Uani 1 1 d . . . H11B H 0.5042 0.4166 0.3569 0.068 Uiso 1 1 calc R . . C12' C 0.5343(4) 0.5556(4) 0.29187(17) 0.0610(10) Uani 1 1 d . . . H12B H 0.6304 0.5074 0.2594 0.073 Uiso 1 1 calc R . . C13' C 0.4691(4) 0.6804(4) 0.28214(16) 0.0583(11) Uani 1 1 d . . . H13B H 0.5216 0.7174 0.2435 0.070 Uiso 1 1 calc R . . C14' C 0.3254(4) 0.7512(3) 0.32974(15) 0.0524(9) Uani 1 1 d . . . H14B H 0.2807 0.8360 0.3226 0.063 Uiso 1 1 calc R . . C15' C 0.2232(4) 0.5054(3) 0.45785(17) 0.0595(10) Uani 1 1 d . . . H15B H 0.1120 0.5618 0.4715 0.071 Uiso 1 1 calc R . . C16' C 0.2829(6) 0.4807(4) 0.53335(19) 0.0938(16) Uani 1 1 d . . . H16D H 0.2776 0.5567 0.5540 0.141 Uiso 1 1 calc R . . H16G H 0.3901 0.4219 0.5221 0.141 Uiso 1 1 calc R . . H16E H 0.2185 0.4479 0.5715 0.141 Uiso 1 1 calc R . . C17' C 0.2323(5) 0.3845(4) 0.4246(2) 0.0848(14) Uani 1 1 d . . . H17G H 0.1753 0.3478 0.4641 0.127 Uiso 1 1 calc R . . H17D H 0.3406 0.3285 0.4093 0.127 Uiso 1 1 calc R . . H17E H 0.1869 0.4014 0.3794 0.127 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 S1 0.0918(8) 0.0984(8) 0.0728(5) 0.0230(5) -0.0436(5) -0.0629(8) S2 0.0710(7) 0.0820(7) 0.0644(5) 0.0328(5) -0.0306(5) -0.0413(7) N1 0.076(2) 0.070(2) 0.0618(15) 0.0190(15) -0.0197(16) -0.041(2) N2 0.080(2) 0.106(3) 0.097(2) 0.021(2) -0.042(2) -0.057(3) C1 0.047(2) 0.047(2) 0.0458(15) 0.0029(15) -0.0169(15) -0.017(2) C2 0.0412(19) 0.045(2) 0.0456(15) 0.0009(15) -0.0090(15) -0.018(2) C3 0.0359(18) 0.0346(18) 0.0423(15) -0.0021(14) -0.0030(14) -0.010(2) C4 0.0416(19) 0.0432(19) 0.0421(14) 0.0032(14) -0.0067(14) -0.018(2) C5 0.047(2) 0.049(2) 0.0423(14) 0.0035(14) -0.0089(14) -0.017(2) C6 0.058(2) 0.061(3) 0.0581(17) 0.0088(18) -0.0174(17) -0.031(3) C7 0.068(3) 0.108(4) 0.084(2) 0.045(3) -0.034(2) -0.027(4) C8 0.100(3) 0.108(3) 0.100(2) 0.035(2) -0.041(2) -0.079(3) C9 0.035(2) 0.046(2) 0.0449(15) 0.0047(15) -0.0071(15) -0.017(2) C10 0.045(2) 0.046(2) 0.0615(17) 0.0035(16) -0.0062(17) -0.021(2) C11 0.063(3) 0.056(2) 0.087(2) 0.012(2) -0.004(2) -0.033(3) C12 0.056(3) 0.079(3) 0.080(2) 0.025(2) -0.002(2) -0.037(3) C13 0.048(3) 0.082(3) 0.0639(19) 0.011(2) 0.0041(19) -0.022(3) C14 0.046(2) 0.057(2) 0.0577(17) 0.0036(18) -0.0007(18) -0.016(2) C15 0.065(3) 0.048(2) 0.084(2) -0.0030(19) 0.006(2) -0.027(3) C16 0.120(5) 0.079(3) 0.080(2) -0.020(2) 0.004(3) -0.028(4) C17 0.074(3) 0.060(3) 0.126(3) 0.003(3) -0.001(3) -0.011(3) S1' 0.0474(6) 0.0722(7) 0.0733(5) 0.0062(5) -0.0255(4) -0.0188(7) S2' 0.0538(6) 0.0909(8) 0.0645(5) -0.0263(5) -0.0129(4) -0.0197(7) N1' 0.066(2) 0.063(2) 0.0643(17) -0.0079(16) 0.0065(18) -0.017(3) N2' 0.066(2) 0.089(3) 0.0658(16) -0.0023(17) -0.0195(16) -0.032(3) C1' 0.058(2) 0.046(2) 0.0455(16) 0.0028(16) -0.0058(17) -0.023(2) C2' 0.043(2) 0.042(2) 0.0419(14) 0.0006(14) -0.0044(14) -0.015(2) C3' 0.042(2) 0.0355(18) 0.0457(14) 0.0015(14) -0.0063(14) -0.015(2) C4' 0.0408(19) 0.046(2) 0.0520(15) -0.0012(15) -0.0076(15) -0.013(2) C5' 0.047(2) 0.051(2) 0.0500(15) 0.0070(15) -0.0115(15) -0.021(2) C6' 0.055(2) 0.057(3) 0.0438(15) -0.0007(16) -0.0075(16) -0.024(3) C7' 0.094(4) 0.139(5) 0.090(3) -0.050(3) -0.019(3) -0.046(4) C8' 0.041(2) 0.090(3) 0.084(2) 0.017(2) -0.0164(19) -0.014(3) C9' 0.037(2) 0.051(2) 0.0426(14) -0.0051(14) -0.0063(14) -0.020(2) C10' 0.035(2) 0.049(2) 0.0448(14) -0.0009(15) -0.0069(15) -0.011(2) C11' 0.043(2) 0.056(2) 0.0628(18) -0.0020(18) -0.0054(18) -0.013(2) C12' 0.042(2) 0.073(3) 0.0584(17) -0.0163(18) 0.0049(17) -0.020(3) C13' 0.052(3) 0.076(3) 0.0514(16) -0.0031(17) 0.0015(17) -0.036(3) C14' 0.055(2) 0.053(2) 0.0508(15) 0.0018(16) -0.0064(17) -0.027(2) C15' 0.047(2) 0.048(2) 0.0658(19) 0.0068(17) 0.0018(18) -0.009(3) C16' 0.128(4) 0.084(3) 0.064(2) 0.021(2) -0.015(3) -0.043(4) C17' 0.084(3) 0.073(3) 0.101(3) 0.002(2) -0.006(2) -0.042(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 S1 C5 1.733(2) . ? S1 C8 1.788(3) . ? S2 C5 1.743(3) . ? S2 C7 1.784(4) . ? N1 C1 1.143(3) . ? N2 C6 1.136(4) . ? C1 C2 1.434(4) . ? C2 C3 1.366(4) . y C2 C6 1.437(4) . ? C3 C4 1.427(3) . y C3 C9 1.500(3) . y C4 C5 1.364(4) . y C4 H4A 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C14 1.372(4) . ? C9 C10 1.403(5) . ? C10 C11 1.399(4) . ? C10 C15 1.514(5) . ? C11 C12 1.368(5) . ? C11 H11A 0.9300 . ? C12 C13 1.359(6) . ? C12 H12A 0.9300 . ? C13 C14 1.391(4) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C17 1.507(6) . ? C15 C16 1.533(5) . ? C15 H15A 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? S1' C5' 1.751(3) . ? S1' C8' 1.783(4) . ? S2' C5' 1.730(3) . ? S2' C7' 1.778(3) . ? N1' C1' 1.146(4) . ? N2' C6' 1.146(4) . ? C1' C2' 1.426(5) . ? C2' C3' 1.382(3) . ? C2' C6' 1.432(5) . ? C3' C4' 1.427(4) . ? C3' C9' 1.478(4) . ? C4' C5' 1.367(4) . ? C4' H4'A 0.9300 . ? C7' H7'A 0.9600 . ? C7' H7'B 0.9600 . ? C7' H7'C 0.9600 . ? C8' H8'A 0.9600 . ? C8' H8'B 0.9600 . ? C8' H8'C 0.9600 . ? C9' C14' 1.400(3) . ? C9' C10' 1.402(5) . ? C10' C11' 1.382(4) . ? C10' C15' 1.521(4) . ? C11' C12' 1.379(4) . ? C11' H11B 0.9300 . ? C12' C13' 1.367(6) . ? C12' H12B 0.9300 . ? C13' C14' 1.380(5) . ? C13' H13B 0.9300 . ? C14' H14B 0.9300 . ? C15' C16' 1.524(5) . ? C15' C17' 1.529(5) . ? C15' H15B 0.9800 . ? C16' H16D 0.9600 . ? C16' H16G 0.9600 . ? C16' H16E 0.9600 . ? C17' H17G 0.9600 . ? C17' H17D 0.9600 . ? C17' H17E 0.9600 . ? 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 C5 S1 C8 105.34(14) . . ? C5 S2 C7 104.19(15) . . ? N1 C1 C2 179.1(3) . . ? C3 C2 C1 122.2(2) . . ? C3 C2 C6 123.7(2) . . ? C1 C2 C6 114.1(3) . . ? C2 C3 C4 119.4(2) . . ? C2 C3 C9 118.0(2) . . ? C4 C3 C9 122.6(2) . . ? C5 C4 C3 130.0(2) . . ? C5 C4 H4A 115.0 . . ? C3 C4 H4A 115.0 . . ? C4 C5 S1 122.44(19) . . ? C4 C5 S2 123.48(18) . . ? S1 C5 S2 114.05(16) . . ? N2 C6 C2 176.2(4) . . ? S2 C7 H7A 109.5 . . ? S2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 121.2(2) . . ? C14 C9 C3 118.2(3) . . ? C10 C9 C3 120.7(3) . . ? C11 C10 C9 116.4(3) . . ? C11 C10 C15 121.3(3) . . ? C9 C10 C15 122.2(2) . . ? C12 C11 C10 121.9(3) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? C12 C13 C14 118.9(4) . . ? C12 C13 H13A 120.6 . . ? C14 C13 H13A 120.6 . . ? C9 C14 C13 120.6(3) . . ? C9 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? C17 C15 C10 112.9(3) . . ? C17 C15 C16 111.0(3) . . ? C10 C15 C16 111.5(3) . . ? C17 C15 H15A 107.0 . . ? C10 C15 H15A 107.0 . . ? C16 C15 H15A 107.0 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C5' S1' C8' 105.17(15) . . ? C5' S2' C7' 105.22(17) . . ? N1' C1' C2' 177.6(3) . . ? C3' C2' C1' 121.5(3) . . ? C3' C2' C6' 122.5(3) . . ? C1' C2' C6' 115.9(2) . . ? C2' C3' C4' 118.7(3) . . ? C2' C3' C9' 118.8(3) . . ? C4' C3' C9' 122.5(2) . . ? C5' C4' C3' 128.9(3) . . ? C5' C4' H4'A 115.5 . . ? C3' C4' H4'A 115.5 . . ? C4' C5' S2' 124.4(2) . . ? C4' C5' S1' 120.8(3) . . ? S2' C5' S1' 114.71(15) . . ? N2' C6' C2' 176.4(4) . . ? S2' C7' H7'A 109.5 . . ? S2' C7' H7'B 109.5 . . ? H7'A C7' H7'B 109.5 . . ? S2' C7' H7'C 109.5 . . ? H7'A C7' H7'C 109.5 . . ? H7'B C7' H7'C 109.5 . . ? S1' C8' H8'A 109.5 . . ? S1' C8' H8'B 109.5 . . ? H8'A C8' H8'B 109.5 . . ? S1' C8' H8'C 109.5 . . ? H8'A C8' H8'C 109.5 . . ? H8'B C8' H8'C 109.5 . . ? C14' C9' C10' 119.7(3) . . ? C14' C9' C3' 119.0(3) . . ? C10' C9' C3' 121.2(2) . . ? C11' C10' C9' 117.9(2) . . ? C11' C10' C15' 121.3(3) . . ? C9' C10' C15' 120.8(3) . . ? C12' C11' C10' 122.1(3) . . ? C12' C11' H11B 118.9 . . ? C10' C11' H11B 118.9 . . ? C13' C12' C11' 119.9(3) . . ? C13' C12' H12B 120.1 . . ? C11' C12' H12B 120.1 . . ? C12' C13' C14' 119.9(3) . . ? C12' C13' H13B 120.1 . . ? C14' C13' H13B 120.1 . . ? C13' C14' C9' 120.5(3) . . ? C13' C14' H14B 119.7 . . ? C9' C14' H14B 119.7 . . ? C10' C15' C16' 111.4(3) . . ? C10' C15' C17' 112.3(3) . . ? C16' C15' C17' 109.6(3) . . ? C10' C15' H15B 107.8 . . ? C16' C15' H15B 107.8 . . ? C17' C15' H15B 107.8 . . ? C15' C16' H16D 109.5 . . ? C15' C16' H16G 109.5 . . ? H16D C16' H16G 109.5 . . ? C15' C16' H16E 109.5 . . ? H16D C16' H16E 109.5 . . ? H16G C16' H16E 109.5 . . ? C15' C17' H17G 109.5 . . ? C15' C17' H17D 109.5 . . ? H17G C17' H17D 109.5 . . ? C15' C17' H17E 109.5 . . ? H17G C17' H17E 109.5 . . ? H17D C17' H17E 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 N1 C1 C2 C3 125(23) . . . . ? N1 C1 C2 C6 -58(23) . . . . ? C1 C2 C3 C4 5.8(4) . . . . y C6 C2 C3 C4 -171.2(3) . . . . y C1 C2 C3 C9 -177.4(3) . . . . y C6 C2 C3 C9 5.7(5) . . . . y C2 C3 C4 C5 -175.1(3) . . . . y C9 C3 C4 C5 8.2(5) . . . . y C3 C4 C5 S1 -177.6(2) . . . . y C3 C4 C5 S2 0.1(5) . . . . y C8 S1 C5 C4 -2.6(3) . . . . ? C8 S1 C5 S2 179.6(2) . . . . ? C7 S2 C5 C4 161.4(3) . . . . ? C7 S2 C5 S1 -20.7(2) . . . . ? C3 C2 C6 N2 172(6) . . . . ? C1 C2 C6 N2 -5(6) . . . . ? C2 C3 C9 C14 -90.1(3) . . . . y C4 C3 C9 C14 86.6(4) . . . . y C2 C3 C9 C10 89.8(4) . . . . y C4 C3 C9 C10 -93.4(3) . . . . y C14 C9 C10 C11 0.6(5) . . . . ? C3 C9 C10 C11 -179.4(3) . . . . ? C14 C9 C10 C15 -177.9(3) . . . . ? C3 C9 C10 C15 2.1(5) . . . . ? C9 C10 C11 C12 -1.3(5) . . . . ? C15 C10 C11 C12 177.2(3) . . . . ? C10 C11 C12 C13 0.6(6) . . . . ? C11 C12 C13 C14 0.9(6) . . . . ? C10 C9 C14 C13 0.8(5) . . . . ? C3 C9 C14 C13 -179.2(3) . . . . ? C12 C13 C14 C9 -1.6(5) . . . . ? C11 C10 C15 C17 -40.2(4) . . . . ? C9 C10 C15 C17 138.2(3) . . . . ? C11 C10 C15 C16 85.6(4) . . . . ? C9 C10 C15 C16 -96.0(3) . . . . ? N1' C1' C2' C3' 26(9) . . . . ? N1' C1' C2' C6' -155(9) . . . . ? C1' C2' C3' C4' 5.4(4) . . . . y C6' C2' C3' C4' -173.7(3) . . . . y C1' C2' C3' C9' -175.6(2) . . . . y C6' C2' C3' C9' 5.3(4) . . . . y C2' C3' C4' C5' -173.3(3) . . . . y C9' C3' C4' C5' 7.7(5) . . . . y C3' C4' C5' S2' -4.4(4) . . . . y C3' C4' C5' S1' 177.1(2) . . . . y C7' S2' C5' C4' 164.4(3) . . . . ? C7' S2' C5' S1' -17.0(2) . . . . ? C8' S1' C5' C4' -7.3(3) . . . . ? C8' S1' C5' S2' 174.09(17) . . . . ? C3' C2' C6' N2' 153(5) . . . . ? C1' C2' C6' N2' -26(6) . . . . ? C2' C3' C9' C14' -94.6(3) . . . . y C4' C3' C9' C14' 84.4(3) . . . . y C2' C3' C9' C10' 88.3(3) . . . . y C4' C3' C9' C10' -92.7(3) . . . . y C14' C9' C10' C11' 2.0(4) . . . . ? C3' C9' C10' C11' 179.1(2) . . . . ? C14' C9' C10' C15' -175.7(2) . . . . ? C3' C9' C10' C15' 1.4(4) . . . . ? C9' C10' C11' C12' -2.3(4) . . . . ? C15' C10' C11' C12' 175.4(3) . . . . ? C10' C11' C12' C13' 1.8(5) . . . . ? C11' C12' C13' C14' -0.9(5) . . . . ? C12' C13' C14' C9' 0.7(4) . . . . ? C10' C9' C14' C13' -1.3(4) . . . . ? C3' C9' C14' C13' -178.4(2) . . . . ? C11' C10' C15' C16' 82.1(4) . . . . ? C9' C10' C15' C16' -100.3(4) . . . . ? C11' C10' C15' C17' -41.3(4) . . . . ? C9' C10' C15' C17' 136.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.687 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.687 _refine_diff_density_max 0.129 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.030 #====================================================================== #_eof # End of Crystallographic Information File #====================================================================== #next file follows #====================================================================== data_f118(4h) _database_code_CSD 171038 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Cyano-5-dimethylamino-3-(2-isopropylphenyl)-5-methylthiopenta-2,4-dienenitrile ; _chemical_name_common ? _chemical_melting_point 399 _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 N3 S' _chemical_formula_weight 311.44 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _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 8.8420(10) _cell_length_b 11.3680(10) _cell_length_c 17.832(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.240(10) _cell_angle_gamma 90.00 _cell_volume 1781.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 33 _cell_measurement_theta_min 5.354 _cell_measurement_theta_max 25.837 _exptl_crystal_description 'rod' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.78 _exptl_crystal_size_mid 0.7 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method '?' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2520 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2342 _reflns_number_gt 2013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXTL, Version 4.2 for MSDOS' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.5730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.094(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2342 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.005 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 S1 S 0.07173(7) 0.97606(6) 0.77787(4) 0.0604(3) Uani 1 1 d . . . N1 N 0.6395(3) 0.7386(2) 0.71028(15) 0.0779(8) Uani 1 1 d . . . N2 N 0.6560(3) 0.7256(3) 0.95499(16) 0.0944(9) Uani 1 1 d . . . N3 N 0.0316(3) 0.8159(2) 0.66728(11) 0.0620(6) Uani 1 1 d . . . C1 C 0.5783(3) 0.7493(2) 0.76309(15) 0.0546(7) Uani 1 1 d . . . C2 C 0.4987(3) 0.7643(2) 0.82770(13) 0.0482(6) Uani 1 1 d . . . C3 C 0.3462(3) 0.79486(19) 0.82023(12) 0.0434(6) Uani 1 1 d . . . C4 C 0.2628(3) 0.7999(2) 0.74830(13) 0.0502(6) Uani 1 1 d . . . H4A H 0.3077 0.7638 0.7094 0.060 Uiso 1 1 calc R . . C5 C 0.1221(3) 0.8518(2) 0.72814(13) 0.0505(6) Uani 1 1 d . . . C6 C 0.5838(3) 0.7432(3) 0.89903(16) 0.0600(7) Uani 1 1 d . . . C7 C -0.1177(3) 0.9442(3) 0.80000(18) 0.0765(9) Uani 1 1 d . . . H7A H -0.1544 1.0087 0.8277 0.115 Uiso 1 1 calc R . . H7B H -0.1162 0.8740 0.8300 0.115 Uiso 1 1 calc R . . H7C H -0.1836 0.9328 0.7541 0.115 Uiso 1 1 calc R . . C8 C -0.0812(3) 0.8899(3) 0.62359(16) 0.0797(9) Uani 1 1 d . . . H8A H -0.0906 0.9632 0.6494 0.120 Uiso 1 1 calc R . . H8B H -0.1778 0.8504 0.6180 0.120 Uiso 1 1 calc R . . H8C H -0.0493 0.9046 0.5747 0.120 Uiso 1 1 calc R . . C9 C 0.0565(4) 0.7016(3) 0.63350(18) 0.0895(10) Uani 1 1 d . . . H9A H 0.1316 0.6587 0.6654 0.134 Uiso 1 1 calc R . . H9B H 0.0914 0.7127 0.5849 0.134 Uiso 1 1 calc R . . H9C H -0.0372 0.6582 0.6279 0.134 Uiso 1 1 calc R . . C10 C 0.2715(3) 0.8123(2) 0.89080(12) 0.0447(6) Uani 1 1 d . . . C11 C 0.1661(3) 0.7303(2) 0.91250(12) 0.0469(6) Uani 1 1 d . . . C12 C 0.0933(3) 0.7573(3) 0.97581(14) 0.0632(7) Uani 1 1 d . . . H12A H 0.0220 0.7049 0.9912 0.076 Uiso 1 1 calc R . . C13 C 0.1233(4) 0.8588(3) 1.01613(16) 0.0741(9) Uani 1 1 d . . . H13A H 0.0700 0.8755 1.0570 0.089 Uiso 1 1 calc R . . C14 C 0.2310(4) 0.9355(3) 0.99662(15) 0.0702(8) Uani 1 1 d . . . H14A H 0.2534 1.0032 1.0250 0.084 Uiso 1 1 calc R . . C15 C 0.3066(3) 0.9123(2) 0.93455(14) 0.0580(7) Uani 1 1 d . . . H15A H 0.3815 0.9637 0.9218 0.070 Uiso 1 1 calc R . . C16 C 0.1380(3) 0.6130(2) 0.87299(13) 0.0512(6) Uani 1 1 d . . . H16A H 0.1989 0.6114 0.8302 0.061 Uiso 1 1 calc R . . C17 C 0.1931(4) 0.5120(3) 0.92616(17) 0.0774(9) Uani 1 1 d . . . H17A H 0.1746 0.4383 0.9006 0.116 Uiso 1 1 calc R . . H17D H 0.1391 0.5139 0.9700 0.116 Uiso 1 1 calc R . . H17B H 0.3001 0.5206 0.9412 0.116 Uiso 1 1 calc R . . C18 C -0.0265(3) 0.5950(3) 0.8421(2) 0.0852(10) Uani 1 1 d . . . H18D H -0.0590 0.6589 0.8090 0.128 Uiso 1 1 calc R . . H18A H -0.0885 0.5923 0.8830 0.128 Uiso 1 1 calc R . . H18B H -0.0363 0.5223 0.8146 0.128 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 S1 0.0555(5) 0.0479(5) 0.0756(5) -0.0002(3) -0.0032(3) -0.0008(3) N1 0.0764(17) 0.0880(19) 0.0746(17) -0.0127(14) 0.0316(15) -0.0205(14) N2 0.0748(18) 0.135(3) 0.0704(17) 0.0031(17) -0.0050(15) 0.0262(17) N3 0.0643(14) 0.0727(15) 0.0461(12) 0.0046(11) -0.0064(11) -0.0015(12) C1 0.0472(15) 0.0568(16) 0.0604(17) -0.0044(13) 0.0089(13) -0.0106(12) C2 0.0473(14) 0.0502(14) 0.0472(14) 0.0011(11) 0.0054(11) -0.0028(11) C3 0.0491(14) 0.0380(12) 0.0431(13) 0.0022(10) 0.0045(10) -0.0050(10) C4 0.0539(15) 0.0588(15) 0.0384(12) 0.0018(11) 0.0068(11) 0.0013(12) C5 0.0532(15) 0.0548(15) 0.0434(13) 0.0089(11) 0.0041(11) -0.0063(12) C6 0.0490(15) 0.0729(18) 0.0581(17) -0.0017(14) 0.0048(13) 0.0059(13) C7 0.0691(19) 0.0725(19) 0.089(2) -0.0078(16) 0.0160(16) -0.0001(15) C8 0.0698(19) 0.108(2) 0.0574(17) 0.0235(17) -0.0098(14) 0.0012(18) C9 0.108(3) 0.092(2) 0.0635(19) -0.0221(17) -0.0128(17) 0.002(2) C10 0.0484(14) 0.0477(14) 0.0371(12) 0.0013(10) 0.0007(10) 0.0038(11) C11 0.0486(14) 0.0517(14) 0.0406(13) 0.0024(11) 0.0057(11) 0.0052(11) C12 0.0686(18) 0.0720(19) 0.0523(15) 0.0029(14) 0.0210(13) 0.0020(14) C13 0.091(2) 0.086(2) 0.0488(16) -0.0119(15) 0.0210(15) 0.0129(18) C14 0.094(2) 0.0647(18) 0.0507(16) -0.0154(14) 0.0018(15) 0.0101(17) C15 0.0662(17) 0.0527(15) 0.0537(15) -0.0042(12) 0.0001(13) -0.0042(13) C16 0.0560(15) 0.0506(14) 0.0480(13) 0.0020(11) 0.0109(11) -0.0030(12) C17 0.101(2) 0.0592(18) 0.0723(19) 0.0046(15) 0.0118(17) 0.0107(16) C18 0.068(2) 0.079(2) 0.105(2) -0.0133(18) -0.0073(17) -0.0091(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 S1 C5 1.751(3) . ? S1 C7 1.799(3) . ? N1 C1 1.142(3) . ? N2 C6 1.142(3) . ? N3 C5 1.340(3) . ? N3 C9 1.459(4) . ? N3 C8 1.463(4) . ? C1 C2 1.424(4) . ? C2 C3 1.385(3) . y C2 C6 1.426(4) . ? C3 C4 1.409(3) . y C3 C10 1.496(3) . y C4 C5 1.389(3) . y C4 H4A 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.394(3) . ? C10 C11 1.402(3) . ? C11 C12 1.394(3) . ? C11 C16 1.515(3) . ? C12 C13 1.370(4) . ? C12 H12A 0.9300 . ? C13 C14 1.364(4) . ? C13 H13A 0.9300 . ? C14 C15 1.379(4) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 C18 1.512(4) . ? C16 C17 1.535(4) . ? C16 H16A 0.9800 . ? C17 H17A 0.9600 . ? C17 H17D 0.9600 . ? C17 H17B 0.9600 . ? C18 H18D 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? 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 C5 S1 C7 104.07(13) . . ? C5 N3 C9 120.1(2) . . ? C5 N3 C8 124.7(2) . . ? C9 N3 C8 114.6(2) . . ? N1 C1 C2 178.4(3) . . ? C3 C2 C1 120.9(2) . . ? C3 C2 C6 122.8(2) . . ? C1 C2 C6 116.3(2) . . ? C2 C3 C4 120.3(2) . . ? C2 C3 C10 117.8(2) . . ? C4 C3 C10 121.7(2) . . ? C5 C4 C3 128.2(2) . . ? C5 C4 H4A 115.9 . . ? C3 C4 H4A 115.9 . . ? N3 C5 C4 121.3(2) . . ? N3 C5 S1 119.56(19) . . ? C4 C5 S1 118.83(19) . . ? N2 C6 C2 177.8(3) . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 120.1(2) . . ? C15 C10 C3 119.1(2) . . ? C11 C10 C3 120.7(2) . . ? C12 C11 C10 117.2(2) . . ? C12 C11 C16 120.2(2) . . ? C10 C11 C16 122.5(2) . . ? C13 C12 C11 122.0(3) . . ? C13 C12 H12A 119.0 . . ? C11 C12 H12A 119.0 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? C14 C15 C10 120.5(3) . . ? C14 C15 H15A 119.7 . . ? C10 C15 H15A 119.7 . . ? C18 C16 C11 113.1(2) . . ? C18 C16 C17 110.6(2) . . ? C11 C16 C17 110.2(2) . . ? C18 C16 H16A 107.6 . . ? C11 C16 H16A 107.6 . . ? C17 C16 H16A 107.6 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17D 109.5 . . ? H17A C17 H17D 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? H17D C17 H17B 109.5 . . ? C16 C18 H18D 109.5 . . ? C16 C18 H18A 109.5 . . ? H18D C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18D C18 H18B 109.5 . . ? H18A C18 H18B 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 N1 C1 C2 C3 16(11) . . . . ? N1 C1 C2 C6 -166(10) . . . . ? C1 C2 C3 C4 6.6(4) . . . . y C6 C2 C3 C4 -171.8(2) . . . . y C1 C2 C3 C10 -178.3(2) . . . . y C6 C2 C3 C10 3.3(3) . . . . y C2 C3 C4 C5 -164.9(2) . . . . y C10 C3 C4 C5 20.2(4) . . . . y C9 N3 C5 C4 17.8(4) . . . . ? C8 N3 C5 C4 -153.1(3) . . . . ? C9 N3 C5 S1 -168.8(2) . . . . ? C8 N3 C5 S1 20.3(3) . . . . ? C3 C4 C5 N3 -155.4(2) . . . . y C3 C4 C5 S1 31.1(3) . . . . y C7 S1 C5 N3 54.3(2) . . . . ? C7 S1 C5 C4 -132.1(2) . . . . ? C3 C2 C6 N2 179(100) . . . . ? C1 C2 C6 N2 1(9) . . . . ? C2 C3 C10 C15 72.6(3) . . . . y C4 C3 C10 C15 -112.4(3) . . . . y C2 C3 C10 C11 -108.2(3) . . . . y C4 C3 C10 C11 66.8(3) . . . . y C15 C10 C11 C12 3.9(3) . . . . ? C3 C10 C11 C12 -175.3(2) . . . . ? C15 C10 C11 C16 -172.2(2) . . . . ? C3 C10 C11 C16 8.6(3) . . . . ? C10 C11 C12 C13 -0.7(4) . . . . ? C16 C11 C12 C13 175.5(3) . . . . ? C11 C12 C13 C14 -2.3(4) . . . . ? C12 C13 C14 C15 2.0(5) . . . . ? C13 C14 C15 C10 1.3(4) . . . . ? C11 C10 C15 C14 -4.3(4) . . . . ? C3 C10 C15 C14 174.9(2) . . . . ? C12 C11 C16 C18 61.2(3) . . . . ? C10 C11 C16 C18 -122.8(3) . . . . ? C12 C11 C16 C17 -63.2(3) . . . . ? C10 C11 C16 C17 112.8(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.202 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.039 #====================================================================== #_eof # End of Crystallographic Information File #====================================================================== #next file follows #====================================================================== data_f158(6h) _database_code_CSD 171039 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Cyano-3-(2-isopropylphenyl)-5,5-bis(pyrrolidino)penta-2,4-dienenitrile ; _chemical_name_common ? _chemical_melting_point 476 _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 N4' _chemical_formula_weight 360.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1540(10) _cell_length_b 12.0410(10) _cell_length_c 12.4450(10) _cell_angle_alpha 104.280(10) _cell_angle_beta 102.500(10) _cell_angle_gamma 106.540(10) _cell_volume 1079.74(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 33 _cell_measurement_theta_min 5.434 _cell_measurement_theta_max 24.309 _exptl_crystal_description 'piece of rod' _exptl_crystal_colour 'yellowish' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method '?' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2881 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0678 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 22.00 _reflns_number_total 2652 _reflns_number_gt 1875 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXTL, Version 4.2 for MSDOS' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0538P)^2^+0.2219P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2652 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2382(4) 0.1139(3) 0.4593(3) 0.0963(11) Uani 1 1 d . . . N2 N 0.6013(4) 0.3378(3) 0.3310(3) 0.0752(9) Uani 1 1 d . . . N3 N -0.2252(3) 0.1339(2) 0.3437(2) 0.0522(7) Uani 1 1 d . . . N4 N -0.0135(3) 0.2692(2) 0.5183(2) 0.0505(6) Uani 1 1 d . . . C5 C -0.0809(4) 0.2347(2) 0.4033(3) 0.0454(7) Uani 1 1 d . . . C4 C -0.0012(3) 0.3103(2) 0.3393(2) 0.0457(7) Uani 1 1 d . . . H4A H -0.0735 0.3453 0.3016 0.055 Uiso 1 1 calc R . . C3 C 0.1661(3) 0.3353(2) 0.3287(2) 0.0428(7) Uani 1 1 d . . . C2 C 0.2971(4) 0.2850(2) 0.3694(2) 0.0486(7) Uani 1 1 d . . . C1 C 0.2628(4) 0.1908(3) 0.4185(3) 0.0624(9) Uani 1 1 d . . . C6 C 0.4642(4) 0.3165(3) 0.3483(3) 0.0530(8) Uani 1 1 d . . . C7 C -0.2805(4) 0.0849(3) 0.2154(3) 0.0749(10) Uani 1 1 d . . . H7A H -0.1840 0.0682 0.1887 0.090 Uiso 1 1 calc R . . H7B H -0.3157 0.1420 0.1812 0.090 Uiso 1 1 calc R . . C8 C -0.4391(5) -0.0325(4) 0.1848(4) 0.1042(15) Uani 1 1 d . . . H8A H -0.5202 -0.0529 0.1074 0.125 Uiso 1 1 calc R . . H8B H -0.3996 -0.1005 0.1888 0.125 Uiso 1 1 calc R . . C9 C -0.5273(5) -0.0019(3) 0.2764(3) 0.0830(11) Uani 1 1 d . . . H9A H -0.6020 -0.0758 0.2850 0.100 Uiso 1 1 calc R . . H9B H -0.6008 0.0455 0.2573 0.100 Uiso 1 1 calc R . . C10 C -0.3700(4) 0.0734(3) 0.3869(3) 0.0642(9) Uani 1 1 d . . . H10A H -0.4003 0.1336 0.4387 0.077 Uiso 1 1 calc R . . H10B H -0.3347 0.0210 0.4280 0.077 Uiso 1 1 calc R . . C11 C -0.0399(5) 0.1894(3) 0.5906(3) 0.0690(9) Uani 1 1 d . . . H11A H -0.0397 0.1089 0.5519 0.083 Uiso 1 1 calc R . . H11B H -0.1519 0.1801 0.6087 0.083 Uiso 1 1 calc R . . C12 C 0.1210(5) 0.2582(4) 0.6995(3) 0.0913(12) Uani 1 1 d . . . H12A H 0.0937 0.2405 0.7670 0.110 Uiso 1 1 calc R . . H12B H 0.2243 0.2367 0.6902 0.110 Uiso 1 1 calc R . . C13 C 0.1553(5) 0.3913(4) 0.7116(3) 0.0828(11) Uani 1 1 d . . . H13A H 0.0712 0.4197 0.7444 0.099 Uiso 1 1 calc R . . H13B H 0.2770 0.4427 0.7603 0.099 Uiso 1 1 calc R . . C14 C 0.1269(4) 0.3912(3) 0.5878(3) 0.0629(9) Uani 1 1 d . . . H14A H 0.0858 0.4568 0.5766 0.076 Uiso 1 1 calc R . . H14B H 0.2368 0.4002 0.5670 0.076 Uiso 1 1 calc R . . C15 C 0.2231(3) 0.4240(3) 0.2656(2) 0.0473(7) Uani 1 1 d . . . C16 C 0.2044(4) 0.3843(3) 0.1473(3) 0.0665(9) Uani 1 1 d . . . C17 C 0.2595(6) 0.4729(5) 0.0960(4) 0.0965(13) Uani 1 1 d . . . H17A H 0.2448 0.4487 0.0165 0.116 Uiso 1 1 calc R . . C18 C 0.3353(6) 0.5956(5) 0.1605(5) 0.1040(15) Uani 1 1 d . . . H18A H 0.3726 0.6532 0.1245 0.125 Uiso 1 1 calc R . . C19 C 0.3560(5) 0.6334(3) 0.2765(4) 0.0872(12) Uani 1 1 d . . . H19A H 0.4082 0.7164 0.3200 0.105 Uiso 1 1 calc R . . C20 C 0.2996(4) 0.5484(3) 0.3291(3) 0.0649(9) Uani 1 1 d . . . H20A H 0.3126 0.5745 0.4083 0.078 Uiso 1 1 calc R . . C21 C 0.1231(6) 0.2489(4) 0.0755(3) 0.0915(12) Uani 1 1 d . . . H21A H 0.1005 0.2029 0.1290 0.110 Uiso 1 1 calc R . . C22 C 0.2533(7) 0.2073(5) 0.0181(4) 0.1338(19) Uani 1 1 d . . . H22A H 0.3655 0.2281 0.0766 0.201 Uiso 1 1 calc R . . H22D H 0.2733 0.2476 -0.0380 0.201 Uiso 1 1 calc R . . H22B H 0.2027 0.1201 -0.0202 0.201 Uiso 1 1 calc R . . C23 C -0.0576(7) 0.2180(5) -0.0149(4) 0.142(2) Uani 1 1 d . . . H23D H -0.1363 0.2453 0.0233 0.213 Uiso 1 1 calc R . . H23A H -0.1106 0.1309 -0.0536 0.213 Uiso 1 1 calc R . . H23B H -0.0392 0.2585 -0.0711 0.213 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.101(2) 0.096(2) 0.158(3) 0.088(3) 0.076(2) 0.064(2) N2 0.0531(17) 0.0727(19) 0.117(2) 0.0418(18) 0.0392(17) 0.0286(15) N3 0.0443(14) 0.0460(14) 0.0669(17) 0.0163(12) 0.0243(12) 0.0134(12) N4 0.0512(15) 0.0510(15) 0.0545(16) 0.0246(12) 0.0207(12) 0.0163(12) C5 0.0401(16) 0.0422(17) 0.061(2) 0.0173(15) 0.0204(14) 0.0203(14) C4 0.0413(17) 0.0487(17) 0.0534(17) 0.0222(14) 0.0171(13) 0.0187(13) C3 0.0401(16) 0.0407(16) 0.0451(16) 0.0124(13) 0.0122(13) 0.0134(13) C2 0.0429(17) 0.0483(17) 0.0657(19) 0.0283(15) 0.0234(14) 0.0193(14) C1 0.056(2) 0.063(2) 0.095(2) 0.038(2) 0.0411(18) 0.0370(17) C6 0.049(2) 0.0483(18) 0.069(2) 0.0243(15) 0.0200(16) 0.0226(15) C7 0.062(2) 0.071(2) 0.074(2) 0.0033(18) 0.0286(18) 0.0101(18) C8 0.069(3) 0.078(3) 0.122(3) -0.008(2) 0.028(2) 0.001(2) C9 0.059(2) 0.063(2) 0.107(3) 0.012(2) 0.029(2) 0.0019(18) C10 0.0497(19) 0.056(2) 0.093(2) 0.0351(18) 0.0300(18) 0.0125(16) C11 0.071(2) 0.077(2) 0.077(2) 0.0462(19) 0.0331(19) 0.0256(19) C12 0.092(3) 0.124(4) 0.073(3) 0.057(2) 0.026(2) 0.039(3) C13 0.086(3) 0.097(3) 0.061(2) 0.025(2) 0.0211(19) 0.030(2) C14 0.066(2) 0.063(2) 0.0551(19) 0.0170(16) 0.0171(16) 0.0207(18) C15 0.0374(16) 0.0539(19) 0.0570(19) 0.0249(15) 0.0168(13) 0.0184(14) C16 0.062(2) 0.083(2) 0.062(2) 0.0365(19) 0.0215(17) 0.0229(18) C17 0.100(3) 0.131(4) 0.074(3) 0.063(3) 0.033(2) 0.034(3) C18 0.096(3) 0.117(4) 0.137(4) 0.094(4) 0.049(3) 0.038(3) C19 0.082(3) 0.065(2) 0.129(4) 0.056(3) 0.039(3) 0.021(2) C20 0.067(2) 0.057(2) 0.080(2) 0.0324(19) 0.0280(18) 0.0228(17) C21 0.102(3) 0.104(3) 0.055(2) 0.018(2) 0.024(2) 0.023(2) C22 0.158(5) 0.148(5) 0.090(3) 0.008(3) 0.044(3) 0.069(4) C23 0.107(4) 0.174(5) 0.088(3) 0.010(3) 0.003(3) 0.014(4) _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 1.152(4) . ? N2 C6 1.153(4) . ? N3 C5 1.331(3) . ? N3 C7 1.473(4) . ? N3 C10 1.481(4) . ? N4 C5 1.326(3) . ? N4 C11 1.474(4) . ? N4 C14 1.484(4) . ? C5 C4 1.459(4) . y C4 C3 1.354(4) . y C4 H4A 0.9300 . ? C3 C2 1.431(4) . y C3 C15 1.503(4) . y C2 C1 1.405(4) . ? C2 C6 1.407(4) . ? C7 C8 1.515(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.500(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.522(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.518(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.509(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.506(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.389(4) . ? C15 C16 1.391(4) . ? C16 C17 1.392(5) . ? C16 C21 1.518(5) . ? C17 C18 1.375(6) . ? C17 H17A 0.9300 . ? C18 C19 1.359(6) . ? C18 H18A 0.9300 . ? C19 C20 1.371(5) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C21 C23 1.529(6) . ? C21 C22 1.530(6) . ? C21 H21A 0.9800 . ? C22 H22A 0.9600 . ? C22 H22D 0.9600 . ? C22 H22B 0.9600 . ? C23 H23D 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? 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 C5 N3 C7 121.1(2) . . ? C5 N3 C10 127.4(3) . . ? C7 N3 C10 110.2(2) . . ? C5 N4 C11 126.1(3) . . ? C5 N4 C14 122.2(2) . . ? C11 N4 C14 110.9(2) . . ? N4 C5 N3 121.7(3) . . ? N4 C5 C4 120.0(3) . . ? N3 C5 C4 118.3(3) . . ? C3 C4 C5 127.4(3) . . ? C3 C4 H4A 116.3 . . ? C5 C4 H4A 116.3 . . ? C4 C3 C2 127.3(2) . . ? C4 C3 C15 117.6(2) . . ? C2 C3 C15 115.1(2) . . ? C1 C2 C6 114.8(2) . . ? C1 C2 C3 123.7(2) . . ? C6 C2 C3 121.0(2) . . ? N1 C1 C2 178.7(3) . . ? N2 C6 C2 177.2(3) . . ? N3 C7 C8 103.7(3) . . ? N3 C7 H7A 111.0 . . ? C8 C7 H7A 111.0 . . ? N3 C7 H7B 111.0 . . ? C8 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? C9 C8 C7 103.1(3) . . ? C9 C8 H8A 111.2 . . ? C7 C8 H8A 111.2 . . ? C9 C8 H8B 111.2 . . ? C7 C8 H8B 111.2 . . ? H8A C8 H8B 109.1 . . ? C8 C9 C10 103.9(3) . . ? C8 C9 H9A 111.0 . . ? C10 C9 H9A 111.0 . . ? C8 C9 H9B 111.0 . . ? C10 C9 H9B 111.0 . . ? H9A C9 H9B 109.0 . . ? N3 C10 C9 103.7(3) . . ? N3 C10 H10A 111.0 . . ? C9 C10 H10A 111.0 . . ? N3 C10 H10B 111.0 . . ? C9 C10 H10B 111.0 . . ? H10A C10 H10B 109.0 . . ? N4 C11 C12 102.8(3) . . ? N4 C11 H11A 111.2 . . ? C12 C11 H11A 111.2 . . ? N4 C11 H11B 111.2 . . ? C12 C11 H11B 111.2 . . ? H11A C11 H11B 109.1 . . ? C13 C12 C11 103.7(3) . . ? C13 C12 H12A 111.0 . . ? C11 C12 H12A 111.0 . . ? C13 C12 H12B 111.0 . . ? C11 C12 H12B 111.0 . . ? H12A C12 H12B 109.0 . . ? C14 C13 C12 103.2(3) . . ? C14 C13 H13A 111.1 . . ? C12 C13 H13A 111.1 . . ? C14 C13 H13B 111.1 . . ? C12 C13 H13B 111.1 . . ? H13A C13 H13B 109.1 . . ? N4 C14 C13 103.4(3) . . ? N4 C14 H14A 111.1 . . ? C13 C14 H14A 111.1 . . ? N4 C14 H14B 111.1 . . ? C13 C14 H14B 111.1 . . ? H14A C14 H14B 109.0 . . ? C20 C15 C16 119.9(3) . . ? C20 C15 C3 118.3(3) . . ? C16 C15 C3 121.8(3) . . ? C15 C16 C17 117.8(3) . . ? C15 C16 C21 121.3(3) . . ? C17 C16 C21 120.8(3) . . ? C18 C17 C16 121.3(4) . . ? C18 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? C19 C18 C17 120.4(4) . . ? C19 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C18 C19 C20 119.7(4) . . ? C18 C19 H19A 120.2 . . ? C20 C19 H19A 120.2 . . ? C19 C20 C15 120.9(3) . . ? C19 C20 H20A 119.6 . . ? C15 C20 H20A 119.6 . . ? C16 C21 C23 111.6(4) . . ? C16 C21 C22 111.6(3) . . ? C23 C21 C22 111.2(4) . . ? C16 C21 H21A 107.4 . . ? C23 C21 H21A 107.4 . . ? C22 C21 H21A 107.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22D 109.5 . . ? H22A C22 H22D 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? H22D C22 H22B 109.5 . . ? C21 C23 H23D 109.5 . . ? C21 C23 H23A 109.5 . . ? H23D C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23D C23 H23B 109.5 . . ? H23A C23 H23B 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 C11 N4 C5 N3 22.0(4) . . . . ? C14 N4 C5 N3 -169.4(3) . . . . ? C11 N4 C5 C4 -160.4(3) . . . . ? C14 N4 C5 C4 8.2(4) . . . . ? C7 N3 C5 N4 -169.5(3) . . . . ? C10 N3 C5 N4 25.3(4) . . . . ? C7 N3 C5 C4 12.9(4) . . . . ? C10 N3 C5 C4 -152.4(3) . . . . ? N4 C5 C4 C3 64.9(4) . . . . y N3 C5 C4 C3 -117.4(3) . . . . y C5 C4 C3 C2 5.7(5) . . . . y C5 C4 C3 C15 -175.4(3) . . . . y C4 C3 C2 C1 6.3(5) . . . . y C15 C3 C2 C1 -172.6(3) . . . . y C4 C3 C2 C6 177.7(3) . . . . y C15 C3 C2 C6 -1.2(4) . . . . y C6 C2 C1 N1 15(17) . . . . ? C3 C2 C1 N1 -173(100) . . . . ? C1 C2 C6 N2 21(7) . . . . ? C3 C2 C6 N2 -151(7) . . . . ? C5 N3 C7 C8 176.2(3) . . . . ? C10 N3 C7 C8 -16.2(4) . . . . ? N3 C7 C8 C9 34.2(4) . . . . ? C7 C8 C9 C10 -39.5(4) . . . . ? C5 N3 C10 C9 158.6(3) . . . . ? C7 N3 C10 C9 -8.0(3) . . . . ? C8 C9 C10 N3 29.3(4) . . . . ? C5 N4 C11 C12 156.9(3) . . . . ? C14 N4 C11 C12 -12.8(3) . . . . ? N4 C11 C12 C13 32.6(4) . . . . ? C11 C12 C13 C14 -40.7(4) . . . . ? C5 N4 C14 C13 177.8(3) . . . . ? C11 N4 C14 C13 -12.1(3) . . . . ? C12 C13 C14 N4 32.1(4) . . . . ? C4 C3 C15 C20 87.0(3) . . . . y C2 C3 C15 C20 -94.0(3) . . . . y C4 C3 C15 C16 -94.3(3) . . . . y C2 C3 C15 C16 84.8(3) . . . . y C20 C15 C16 C17 -1.8(5) . . . . ? C3 C15 C16 C17 179.5(3) . . . . ? C20 C15 C16 C21 179.4(3) . . . . ? C3 C15 C16 C21 0.7(5) . . . . ? C15 C16 C17 C18 2.0(6) . . . . ? C21 C16 C17 C18 -179.2(4) . . . . ? C16 C17 C18 C19 -0.9(7) . . . . ? C17 C18 C19 C20 -0.5(6) . . . . ? C18 C19 C20 C15 0.7(6) . . . . ? C16 C15 C20 C19 0.5(5) . . . . ? C3 C15 C20 C19 179.2(3) . . . . ? C15 C16 C21 C23 113.1(4) . . . . ? C17 C16 C21 C23 -65.7(5) . . . . ? C15 C16 C21 C22 -121.9(4) . . . . ? C17 C16 C21 C22 59.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.171 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.033 #====================================================================== #_eof # End of Crystallographic Information File