Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Gordon, John' 'Cowley, Lan H.' 'Jones, Jamie N.' 'Keogh, D. Webster' 'Scott, Brian L.' 'Shukla, Piyush' _publ_contact_author_name 'Dr John Gordon' _publ_contact_author_address ; Chemistry Division Los Alamos National Laboratory MS J514 Los Alamos New Mexico 87545 UNITED STATES OF AMERICA ; _publ_contact_author_email 'JGORDON@LANL.GOV' _publ_section_title ; Dialkyl aluminum amides: new reagents for the conversion of C=O into C=NR functionalities ; data_ccd516m _database_code_CSD 184628 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Al2 F4 N2' _chemical_formula_weight 370.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Al' 'Al' 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.241(5) _cell_length_b 7.324(2) _cell_length_c 18.512(7) _cell_angle_alpha 90.00 _cell_angle_beta 106.367(6) _cell_angle_gamma 90.00 _cell_volume 1852.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular slab' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type 'none applied' _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4/CCD' _diffrn_measurement_method ' \f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 2' _diffrn_reflns_number 4813 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1698 _reflns_number_gt 1387 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 4.210(Bruker, 1996)' _computing_cell_refinement 'SAINT 4.05 (Bruker, 1996)' _computing_data_reduction 'SAINT 4.05 (Bruker, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.10 (Bruker, 1996)' _computing_publication_material 'SHELXTL 5.10 (Bruker, 1996)' _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^)+(0.0463P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1698 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.395 _refine_ls_restrained_S_all 1.395 _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 Al1 Al 1.09929(5) 1.07130(10) 0.29543(4) 0.0327(2) Uani 1 1 d . . . F1 F 0.94512(12) 0.44664(19) 0.39203(9) 0.0525(5) Uani 1 1 d . . . F2 F 0.83386(14) 0.9194(2) 0.51492(10) 0.0647(5) Uani 1 1 d . . . N1 N 0.96978(15) 1.0618(3) 0.31407(11) 0.0319(5) Uani 1 1 d . . . HN1 H 0.962(3) 1.157(5) 0.3300(19) 0.080 Uiso 1 1 d . . . C1 C 1.1840(2) 0.8635(4) 0.33032(17) 0.0452(7) Uani 1 1 d . . . HC1A H 1.242(3) 0.881(5) 0.3205(18) 0.080 Uiso 1 1 d . . . HC1B H 1.164(2) 0.744(5) 0.3084(18) 0.080 Uiso 1 1 d . . . HC1C H 1.196(2) 0.851(5) 0.3811(19) 0.080 Uiso 1 1 d . . . C2 C 1.1427(2) 1.3221(4) 0.31468(18) 0.0455(7) Uani 1 1 d . . . HC2A H 1.200(3) 1.347(5) 0.3024(18) 0.080 Uiso 1 1 d . . . HC2B H 1.102(3) 1.399(5) 0.289(2) 0.080 Uiso 1 1 d . . . HC2C H 1.156(3) 1.362(5) 0.3654(19) 0.080 Uiso 1 1 d . . . C3 C 0.94277(16) 0.9324(3) 0.36215(12) 0.0302(6) Uani 1 1 d . . . C4 C 0.95812(18) 0.7475(4) 0.35403(13) 0.0357(6) Uani 1 1 d . . . HC4 H 0.987(2) 0.708(5) 0.3176(19) 0.080 Uiso 1 1 d . . . C5 C 0.93022(18) 0.6272(3) 0.40064(14) 0.0362(6) Uani 1 1 d . . . C6 C 0.88872(19) 0.6776(4) 0.45552(14) 0.0398(7) Uani 1 1 d . . . HC6 H 0.872(2) 0.595(5) 0.4854(19) 0.080 Uiso 1 1 d . . . C7 C 0.87486(19) 0.8606(4) 0.46148(13) 0.0406(6) Uani 1 1 d . . . C8 C 0.90023(19) 0.9897(4) 0.41697(13) 0.0351(6) Uani 1 1 d . . . HC8 H 0.893(3) 1.107(5) 0.4252(18) 0.080 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 Al1 0.0359(4) 0.0292(4) 0.0355(4) -0.0032(3) 0.0142(3) -0.0031(3) F1 0.0687(11) 0.0297(8) 0.0634(10) 0.0068(7) 0.0260(9) 0.0023(8) F2 0.0924(14) 0.0624(12) 0.0602(11) -0.0079(8) 0.0556(10) -0.0099(10) N1 0.0413(12) 0.0236(11) 0.0346(11) 0.0008(9) 0.0170(9) 0.0001(10) C1 0.0453(17) 0.0429(17) 0.0475(16) -0.0032(14) 0.0132(14) 0.0028(14) C2 0.0509(19) 0.0391(17) 0.0488(17) -0.0054(13) 0.0176(14) -0.0085(14) C3 0.0279(12) 0.0342(14) 0.0296(12) 0.0007(10) 0.0097(10) -0.0011(11) C4 0.0394(15) 0.0328(14) 0.0374(14) 0.0002(11) 0.0149(11) 0.0012(12) C5 0.0372(14) 0.0273(13) 0.0423(14) 0.0024(11) 0.0083(12) 0.0005(11) C6 0.0413(15) 0.0444(17) 0.0350(14) 0.0069(12) 0.0128(12) -0.0091(13) C7 0.0434(15) 0.0507(17) 0.0328(13) -0.0053(12) 0.0189(12) -0.0079(13) C8 0.0398(15) 0.0327(14) 0.0348(13) -0.0044(11) 0.0137(11) -0.0027(12) _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 Al1 C1 1.937(3) . ? Al1 C2 1.939(3) . ? Al1 N1 1.971(2) . ? Al1 N1 1.989(2) 2_755 ? Al1 Al1 2.8540(17) 2_755 ? F1 C5 1.356(3) . ? F2 C7 1.353(3) . ? N1 C3 1.425(3) . ? N1 Al1 1.989(2) 2_755 ? C3 C8 1.386(3) . ? C3 C4 1.386(3) . ? C4 C5 1.369(3) . ? C5 C6 1.363(4) . ? C6 C7 1.364(4) . ? C7 C8 1.368(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Al1 C2 123.12(16) . . ? C1 Al1 N1 116.10(12) . . ? C2 Al1 N1 105.50(11) . . ? C1 Al1 N1 113.28(11) . 2_755 ? C2 Al1 N1 105.13(12) . 2_755 ? N1 Al1 N1 87.64(9) . 2_755 ? C1 Al1 Al1 128.13(10) . 2_755 ? C2 Al1 Al1 108.68(10) . 2_755 ? N1 Al1 Al1 44.15(7) . 2_755 ? N1 Al1 Al1 43.63(6) 2_755 2_755 ? C3 N1 Al1 124.28(16) . . ? C3 N1 Al1 121.10(15) . 2_755 ? Al1 N1 Al1 92.22(9) . 2_755 ? C8 C3 C4 119.4(2) . . ? C8 C3 N1 120.4(2) . . ? C4 C3 N1 120.2(2) . . ? C5 C4 C3 118.6(2) . . ? F1 C5 C6 117.9(2) . . ? F1 C5 C4 118.1(2) . . ? C6 C5 C4 124.0(3) . . ? C5 C6 C7 115.5(2) . . ? F2 C7 C6 118.3(2) . . ? F2 C7 C8 117.5(2) . . ? C6 C7 C8 124.2(2) . . ? C7 C8 C3 118.4(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.309 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.049 #====================END===================== data_p1bar _database_code_CSD 184629 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common pentafluorophenyl alpha-diimine _chemical_melting_point ? _chemical_formula_moiety [(C6F5)NC(CH3)C(CH3)N(C6F5)] _chemical_formula_sum 'C16 H6 F10 N2' _chemical_formula_weight 416.23 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' 'F' 'F' 0.0171 0.0103 '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 6.3833(13) _cell_length_b 7.7232(15) _cell_length_c 8.2726(17) _cell_angle_alpha 91.79(3) _cell_angle_beta 107.64(3) _cell_angle_gamma 103.10(3) _cell_volume 376.34(13) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3.46 _cell_measurement_theta_max 30.17 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.837 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 206 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min none _exptl_absorpt_correction_T_max none _exptl_absorpt_process_details N/A _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Nonius Kappa CCD _diffrn_measurement_method omega scans _diffrn_detector_area_resol_mean 621 X 576 pixels _diffrn_standards_number N/A _diffrn_standards_interval_count N/A _diffrn_standards_interval_time N/A _diffrn_standards_decay_% N/A _diffrn_reflns_number 4727 _diffrn_reflns_av_R_equivalents 0.1755 _diffrn_reflns_av_sigmaI/netI 0.1263 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 30.17 _reflns_number_total 1955 _reflns_number_gt 1275 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect (Nonius BV, R. W. W. Hooft)' _computing_cell_refinement 'Denzo SMN (Otwinoswski and Minor, 1997)' _computing_data_reduction 'Scalepack (Otwinoswski and Minor, 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material '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^, conventiona 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^)+(0.1462P)^2^+0.1484P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1955 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1317 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.2725 _refine_ls_wR_factor_gt 0.2394 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 C11 C 0.7927(6) 0.5431(4) 0.7848(4) 0.0343(8) Uani 1 1 d . . . F4 F 1.3130(4) 1.2289(3) 0.5550(3) 0.0445(6) Uani 1 1 d . . . H2 H 0.651(8) 0.515(6) 0.817(6) 0.065(14) Uiso 1 1 d . . . H1 H 0.790(7) 0.646(6) 0.729(5) 0.048(11) Uiso 1 1 d . . . H3 H 0.787(7) 0.446(6) 0.689(6) 0.047(11) Uiso 1 1 d . . . F6 F 1.2352(3) 1.0474(2) 1.0743(2) 0.0360(5) Uani 1 1 d . . . F2 F 1.1896(4) 0.6198(2) 0.6375(3) 0.0419(6) Uani 1 1 d . . . F3 F 1.2598(4) 0.8838(3) 0.4389(2) 0.0439(6) Uani 1 1 d . . . F5 F 1.2946(4) 1.3090(2) 0.8721(3) 0.0417(6) Uani 1 1 d . . . N N 1.1814(5) 0.6942(3) 0.9723(3) 0.0298(6) Uani 1 1 d . . . C1 C 1.2027(5) 0.8250(4) 0.8596(4) 0.0280(7) Uani 1 1 d . . . C5 C 1.2729(6) 1.1383(4) 0.8152(5) 0.0334(8) Uani 1 1 d . . . C6 C 1.2387(6) 1.0045(4) 0.9173(4) 0.0286(7) Uani 1 1 d . . . C3 C 1.2529(6) 0.9230(4) 0.5953(4) 0.0331(8) Uani 1 1 d . . . C4 C 1.2808(6) 1.0993(4) 0.6553(4) 0.0324(8) Uani 1 1 d . . . C10 C 0.9985(5) 0.5668(4) 0.9365(4) 0.0266(7) Uani 1 1 d . . . C2 C 1.2143(6) 0.7891(4) 0.6970(4) 0.0332(8) Uani 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 C11 0.044(2) 0.0230(15) 0.0341(17) 0.0119(13) 0.0133(15) 0.0024(13) F4 0.0565(14) 0.0335(11) 0.0458(12) 0.0247(9) 0.0207(10) 0.0067(9) F6 0.0494(13) 0.0273(9) 0.0343(11) 0.0025(7) 0.0206(9) 0.0058(8) F2 0.0660(15) 0.0210(9) 0.0408(12) 0.0002(8) 0.0258(11) 0.0035(9) F3 0.0606(14) 0.0417(12) 0.0306(11) 0.0066(9) 0.0227(10) 0.0037(10) F5 0.0564(14) 0.0163(9) 0.0589(14) 0.0089(8) 0.0275(11) 0.0088(8) N 0.0435(16) 0.0172(11) 0.0299(13) 0.0070(10) 0.0151(12) 0.0047(11) C1 0.0370(17) 0.0180(13) 0.0308(16) 0.0079(11) 0.0143(13) 0.0048(12) C5 0.0384(19) 0.0185(13) 0.0456(19) 0.0069(12) 0.0165(15) 0.0071(12) C6 0.0341(17) 0.0228(14) 0.0288(15) 0.0059(12) 0.0114(13) 0.0047(12) C3 0.039(2) 0.0322(16) 0.0290(16) 0.0071(13) 0.0146(14) 0.0058(14) C4 0.0379(19) 0.0249(15) 0.0362(17) 0.0164(12) 0.0150(14) 0.0051(13) C10 0.0368(17) 0.0171(12) 0.0297(16) 0.0046(11) 0.0160(13) 0.0062(12) C2 0.045(2) 0.0206(13) 0.0351(17) 0.0033(12) 0.0171(15) 0.0036(13) _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 C11 C10 1.487(5) . ? F4 C4 1.340(3) . ? F6 C6 1.339(4) . ? F2 C2 1.340(3) . ? F3 C3 1.335(4) . ? F5 C5 1.348(4) . ? N C10 1.293(4) . ? N C1 1.408(4) . ? C1 C2 1.392(4) . ? C1 C6 1.397(4) . ? C5 C4 1.366(5) . ? C5 C6 1.376(4) . ? C3 C2 1.379(4) . ? C3 C4 1.388(5) . ? C10 C10 1.494(5) 2_767 ? 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 C10 N C1 120.2(3) . . ? C2 C1 C6 116.7(3) . . ? C2 C1 N 123.6(3) . . ? C6 C1 N 119.3(3) . . ? F5 C5 C4 119.7(3) . . ? F5 C5 C6 119.8(3) . . ? C4 C5 C6 120.5(3) . . ? F6 C6 C5 119.1(3) . . ? F6 C6 C1 119.3(3) . . ? C5 C6 C1 121.6(3) . . ? F3 C3 C2 120.5(3) . . ? F3 C3 C4 119.9(3) . . ? C2 C3 C4 119.5(3) . . ? F4 C4 C5 120.8(3) . . ? F4 C4 C3 119.6(3) . . ? C5 C4 C3 119.6(3) . . ? N C10 C11 126.4(3) . . ? N C10 C10 114.8(3) . 2_767 ? C11 C10 C10 118.8(3) . 2_767 ? F2 C2 C3 118.7(3) . . ? F2 C2 C1 119.3(3) . . ? C3 C2 C1 122.0(3) . . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 30.17 _diffrn_measured_fraction_theta_full 0.878 _refine_diff_density_max 0.513 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.107 #===============END=================== data_use41 _database_code_CSD 184630 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common pentafluorophenyl beta-aminoenone _chemical_melting_point ? _chemical_formula_moiety [(C6F5)NC(CH3)CH2C(O)CH3] _chemical_formula_sum 'C11 H8 F5 N O' _chemical_formula_weight 265.18 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' 'F' 'F' 0.0171 0.0103 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.830(5) _cell_length_b 8.734(5) _cell_length_c 11.608(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.433(3) _cell_angle_gamma 90.000(5) _cell_volume 1098.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 30.52 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min none _exptl_absorpt_correction_T_max none _exptl_absorpt_process_details N/A _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Nonius Kappa CCD _diffrn_measurement_method omega scans _diffrn_detector_area_resol_mean 621 X 576 pixels _diffrn_standards_number N/A _diffrn_standards_interval_count N/A _diffrn_standards_interval_time N/A _diffrn_standards_decay_% N/A _diffrn_reflns_number 12000 _diffrn_reflns_av_R_equivalents 0.1326 _diffrn_reflns_av_sigmaI/netI 0.1568 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 30.52 _reflns_number_total 2941 _reflns_number_gt 1240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect (Nonius BV, R. W. W. Hooft)' _computing_cell_refinement 'Denzo SMN (Otwinoswski and Minor, 1997)' _computing_data_reduction 'Scalepack (Otwinoswski and Minor, 1997)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material '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^)+(0.0494P)^2^+1.1346P] 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 0.003(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2941 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2132 _refine_ls_R_factor_gt 0.0723 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 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 F11 F 0.67637(17) 0.3104(2) 0.41193(15) 0.0460(6) Uani 1 1 d . . . F15 F 0.61618(17) -0.0669(2) 0.12789(15) 0.0456(6) Uani 1 1 d . . . F14 F 0.85102(19) -0.0316(3) 0.05562(16) 0.0576(7) Uani 1 1 d . . . F13 F 1.00097(18) 0.1767(3) 0.16149(19) 0.0628(7) Uani 1 1 d . . . F12 F 0.91348(18) 0.3423(3) 0.34113(19) 0.0613(7) Uani 1 1 d . . . O O 0.36137(19) 0.0054(3) 0.47391(17) 0.0392(6) Uani 1 1 d . . . N1 N 0.5176(2) 0.1006(3) 0.3104(2) 0.0327(7) Uani 1 1 d . . . C2 C 0.4140(3) 0.1268(4) 0.2482(3) 0.0324(8) Uani 1 1 d . . . C15 C 0.7185(3) 0.2253(4) 0.3240(3) 0.0343(8) Uiso 1 1 d . . . C12 C 0.8081(3) 0.0537(4) 0.1437(3) 0.0409(9) Uani 1 1 d . . . C11 C 0.6884(3) 0.0376(4) 0.1809(3) 0.0353(8) Uani 1 1 d . . . C10 C 0.6391(3) 0.1226(4) 0.2706(2) 0.0315(8) Uani 1 1 d . . . C14 C 0.8381(3) 0.2414(4) 0.2879(3) 0.0424(9) Uani 1 1 d . . . C13 C 0.8837(3) 0.1573(4) 0.1977(3) 0.0445(9) Uani 1 1 d . . . C4 C 0.2765(3) 0.0424(4) 0.4073(3) 0.0352(8) Uani 1 1 d . . . C3 C 0.2997(3) 0.0983(4) 0.2940(3) 0.0347(8) Uani 1 1 d . . . C1 C 0.4282(4) 0.1937(5) 0.1306(3) 0.0429(10) Uani 1 1 d . . . C5 C 0.1452(4) 0.0303(7) 0.4481(4) 0.0530(11) Uani 1 1 d . . . H5A H 0.135(5) -0.050(7) 0.494(5) 0.11(2) Uiso 1 1 d . . . H5C H 0.122(5) 0.104(7) 0.494(5) 0.12(2) Uiso 1 1 d . . . H1A H 0.459(3) 0.125(4) 0.079(3) 0.050(11) Uiso 1 1 d . . . H3 H 0.235(3) 0.123(3) 0.253(2) 0.026(8) Uiso 1 1 d . . . H1C H 0.490(4) 0.275(5) 0.127(3) 0.061(12) Uiso 1 1 d . . . H1B H 0.348(4) 0.224(4) 0.104(3) 0.058(11) Uiso 1 1 d . . . H5B H 0.089(4) 0.030(5) 0.386(4) 0.090(15) Uiso 1 1 d . . . H1 H 0.503(3) 0.077(4) 0.378(3) 0.051(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F11 0.0493(12) 0.0431(13) 0.0455(11) -0.0111(9) -0.0019(9) -0.0029(10) F15 0.0575(13) 0.0385(13) 0.0406(11) -0.0078(9) -0.0054(9) -0.0005(10) F14 0.0602(14) 0.0660(15) 0.0468(12) 0.0000(11) 0.0122(10) 0.0233(12) F13 0.0361(12) 0.0752(17) 0.0771(15) 0.0177(13) 0.0109(10) 0.0042(11) F12 0.0457(13) 0.0589(16) 0.0792(15) -0.0020(12) -0.0122(11) -0.0160(11) O 0.0366(13) 0.0482(15) 0.0328(12) 0.0013(10) -0.0018(10) -0.0010(11) N1 0.0326(17) 0.0365(18) 0.0290(16) 0.0019(12) -0.0012(13) -0.0037(13) C2 0.038(2) 0.027(2) 0.0316(17) -0.0033(14) -0.0044(15) -0.0001(15) C12 0.045(2) 0.044(2) 0.0337(19) 0.0042(16) 0.0038(16) 0.0145(19) C11 0.043(2) 0.0304(19) 0.0327(18) 0.0029(14) -0.0024(15) 0.0005(16) C10 0.0357(19) 0.0316(19) 0.0273(16) 0.0052(14) -0.0013(14) -0.0001(15) C14 0.037(2) 0.041(2) 0.049(2) 0.0055(18) -0.0076(17) -0.0068(17) C13 0.030(2) 0.054(3) 0.049(2) 0.0147(19) 0.0071(16) 0.0053(19) C4 0.036(2) 0.029(2) 0.0411(19) -0.0045(15) -0.0024(15) -0.0020(16) C3 0.030(2) 0.035(2) 0.0388(19) -0.0014(15) -0.0086(16) 0.0005(17) C1 0.044(2) 0.045(3) 0.039(2) 0.0086(18) -0.0023(18) 0.001(2) C5 0.033(2) 0.076(3) 0.050(3) 0.004(3) 0.0043(19) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F11 C15 1.345(4) . ? F15 C11 1.348(4) . ? F14 C12 1.350(4) . ? F13 C13 1.351(4) . ? F12 C14 1.348(4) . ? O C4 1.240(4) . ? N1 C2 1.349(4) . ? N1 C10 1.411(4) . ? C2 C3 1.374(4) . ? C2 C1 1.494(5) . ? C15 C14 1.372(4) . ? C15 C10 1.385(4) . ? C12 C13 1.369(5) . ? C12 C11 1.376(5) . ? C11 C10 1.389(4) . ? C14 C13 1.374(5) . ? C4 C3 1.427(5) . ? C4 C5 1.506(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C10 125.2(3) . . ? N1 C2 C3 120.7(3) . . ? N1 C2 C1 117.7(3) . . ? C3 C2 C1 121.6(3) . . ? F11 C15 C14 120.1(3) . . ? F11 C15 C10 119.0(3) . . ? C14 C15 C10 120.9(3) . . ? F14 C12 C13 120.2(3) . . ? F14 C12 C11 120.7(3) . . ? C13 C12 C11 119.1(3) . . ? F15 C11 C12 118.1(3) . . ? F15 C11 C10 118.6(3) . . ? C12 C11 C10 123.2(3) . . ? C15 C10 C11 116.2(3) . . ? C15 C10 N1 121.3(3) . . ? C11 C10 N1 122.5(3) . . ? F12 C14 C15 119.8(3) . . ? F12 C14 C13 118.6(3) . . ? C15 C14 C13 121.5(3) . . ? F13 C13 C12 120.1(3) . . ? F13 C13 C14 120.9(3) . . ? C12 C13 C14 119.0(3) . . ? O C4 C3 121.9(3) . . ? O C4 C5 118.9(3) . . ? C3 C4 C5 119.2(3) . . ? C2 C3 C4 125.7(3) . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.227 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.059 #=========END==============