Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_([1-(Dimethylamino)-8-naphthyl]lithium·THF)2 _database_code_CSD 161688 _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Bauer, W.' 'Betz, Jurgen' 'Hampel, Frank' _publ_contact_author_name 'Dr W Bauer' _publ_contact_author_address ; Dr W Bauer Institut fur Organische Chemie Universitat Erlangen-Nurnberg Henkestrasse 42 D-91054 Erlangen GERMANY ; _publ_contact_author_email 'BAUER@ORGANIK.UNI-ERLANGEN.DE' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ([1-(Dimethylamino)-8-naphthyl]lithium·THF)2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Li N O' _chemical_formula_weight 249.27 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' 'Li' 'Li' -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 11.5897(6) _cell_length_b 11.7592(8) _cell_length_c 11.3237(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.222(3) _cell_angle_gamma 90.00 _cell_volume 1457.22(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type SCALEPACK _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4266 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2559 _reflns_number_gt 1897 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0943P)^2^+0.7975P] 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 2559 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _refine_ls_shift/su_max 0.042 _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 Li1 Li 0.4314(3) -0.0289(3) 0.0499(3) 0.0385(8) Uani 1 1 d . . . N1 N 0.60922(16) 0.20046(15) -0.00189(15) 0.0364(4) Uani 1 1 d . . . C1 C 0.71684(18) 0.18839(18) 0.10736(19) 0.0360(5) Uani 1 1 d . . . C2 C 0.8126(2) 0.2638(2) 0.1326(2) 0.0449(6) Uani 1 1 d . . . H2 H 0.8096 0.3242 0.0760 0.054 Uiso 1 1 calc R . . C3 C 0.9150(2) 0.2524(2) 0.2413(2) 0.0528(6) Uani 1 1 d . . . H3 H 0.9811 0.3045 0.2570 0.063 Uiso 1 1 calc R . . C4 C 0.9197(2) 0.1678(2) 0.3234(2) 0.0504(6) Uani 1 1 d . . . H4 H 0.9880 0.1627 0.3979 0.061 Uiso 1 1 calc R . . C5 C 0.8274(2) -0.0008(2) 0.3864(2) 0.0489(6) Uani 1 1 d . . . H5 H 0.8944 -0.0057 0.4621 0.059 Uiso 1 1 calc R . . C6 C 0.7354(2) -0.0777(2) 0.3622(2) 0.0489(6) Uani 1 1 d . . . H6 H 0.7367 -0.1351 0.4218 0.059 Uiso 1 1 calc R . . C7 C 0.6381(2) -0.0722(2) 0.2485(2) 0.0422(5) Uani 1 1 d . . . H7 H 0.5770 -0.1294 0.2333 0.051 Uiso 1 1 calc R . . C8 C 0.62387(18) 0.01001(18) 0.15664(18) 0.0350(5) Uani 1 1 d . . . C9 C 0.72043(17) 0.09351(18) 0.18831(18) 0.0336(5) Uani 1 1 d . . . C10 C 0.82439(18) 0.08655(19) 0.3002(2) 0.0397(5) Uani 1 1 d . . . C21 C 0.6283(2) 0.2709(2) -0.1012(2) 0.0519(6) Uani 1 1 d . . . H21A H 0.6968 0.2403 -0.1240 0.078 Uiso 1 1 calc R . . H21B H 0.6468 0.3491 -0.0712 0.078 Uiso 1 1 calc R . . H21C H 0.5542 0.2701 -0.1747 0.078 Uiso 1 1 calc R . . C22 C 0.5059(2) 0.2470(2) 0.0320(2) 0.0427(6) Uani 1 1 d . . . H22A H 0.4929 0.2003 0.0982 0.064 Uiso 1 1 calc R . . H22B H 0.4318 0.2462 -0.0416 0.064 Uiso 1 1 calc R . . H22C H 0.5244 0.3252 0.0620 0.064 Uiso 1 1 calc R . . O30 O 0.31040(14) 0.03049(16) 0.11700(14) 0.0525(5) Uani 1 1 d . . . C31 C 0.1906(3) 0.0622(4) 0.0429(3) 0.1014(15) Uani 1 1 d . . . H31A H 0.1507 -0.0013 -0.0131 0.122 Uiso 1 1 calc R . . H31B H 0.1937 0.1288 -0.0094 0.122 Uiso 1 1 calc R . . C32 C 0.1222(3) 0.0899(4) 0.1250(3) 0.0907(12) Uani 1 1 d . . . H32A H 0.0624 0.0292 0.1229 0.109 Uiso 1 1 calc R . . H32B H 0.0776 0.1624 0.0994 0.109 Uiso 1 1 calc R . . C33 C 0.2135(3) 0.1001(3) 0.2524(3) 0.0738(9) Uani 1 1 d . . . H33A H 0.2358 0.1806 0.2736 0.089 Uiso 1 1 calc R . . H33B H 0.1816 0.0674 0.3161 0.089 Uiso 1 1 calc R . . C34 C 0.3189(3) 0.0347(3) 0.2444(2) 0.0663(8) Uani 1 1 d . . . H34A H 0.3961 0.0720 0.2944 0.080 Uiso 1 1 calc R . . H34B H 0.3176 -0.0432 0.2771 0.080 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 Li1 0.0371(18) 0.043(2) 0.0366(17) -0.0023(16) 0.0142(15) 0.0008(16) N1 0.0415(10) 0.0382(10) 0.0317(9) 0.0019(7) 0.0149(7) -0.0028(8) C1 0.0350(11) 0.0398(12) 0.0364(11) -0.0069(9) 0.0161(9) -0.0008(9) C2 0.0463(13) 0.0414(13) 0.0518(13) -0.0055(10) 0.0228(11) -0.0060(10) C3 0.0352(12) 0.0567(16) 0.0678(16) -0.0134(13) 0.0188(11) -0.0100(11) C4 0.0297(11) 0.0577(15) 0.0578(14) -0.0088(12) 0.0062(10) 0.0040(11) C5 0.0362(12) 0.0559(15) 0.0446(13) 0.0036(11) -0.0003(9) 0.0131(11) C6 0.0517(14) 0.0452(14) 0.0430(13) 0.0089(11) 0.0066(11) 0.0071(11) C7 0.0432(12) 0.0418(13) 0.0389(12) 0.0038(10) 0.0099(10) -0.0008(10) C8 0.0356(11) 0.0386(12) 0.0320(10) -0.0028(9) 0.0128(8) 0.0008(9) C9 0.0319(11) 0.0377(12) 0.0340(10) -0.0044(9) 0.0147(9) 0.0034(9) C10 0.0296(11) 0.0432(12) 0.0450(12) -0.0056(10) 0.0107(9) 0.0077(9) C21 0.0666(16) 0.0500(14) 0.0400(12) 0.0047(10) 0.0188(11) -0.0146(12) C22 0.0431(12) 0.0448(13) 0.0383(12) -0.0007(10) 0.0108(10) 0.0063(10) O30 0.0391(9) 0.0754(12) 0.0443(9) -0.0084(8) 0.0155(7) 0.0054(8) C31 0.0454(16) 0.180(4) 0.0674(19) -0.040(2) 0.0035(14) 0.035(2) C32 0.0460(16) 0.147(3) 0.078(2) -0.038(2) 0.0188(15) 0.0142(19) C33 0.0689(19) 0.097(2) 0.0624(17) -0.0126(16) 0.0307(15) 0.0142(17) C34 0.0604(16) 0.097(2) 0.0460(14) -0.0015(14) 0.0240(12) 0.0105(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 Li1 O30 1.932(4) . ? Li1 N1 2.102(4) 3_655 ? Li1 C8 2.207(4) . ? Li1 C8 2.223(4) 3_655 ? Li1 Li1 2.335(7) 3_655 ? Li1 C7 2.740(4) . ? Li1 C1 2.761(4) 3_655 ? N1 C1 1.446(3) . ? N1 C21 1.471(3) . ? N1 C22 1.478(3) . ? N1 Li1 2.102(4) 3_655 ? C1 C2 1.375(3) . ? C1 C9 1.436(3) . ? C1 Li1 2.761(4) 3_655 ? C2 C3 1.407(3) . ? C3 C4 1.350(4) . ? C4 C10 1.419(3) . ? C5 C6 1.356(3) . ? C5 C10 1.409(3) . ? C6 C7 1.406(3) . ? C7 C8 1.390(3) . ? C8 C9 1.443(3) . ? C8 Li1 2.223(4) 3_655 ? C9 C10 1.435(3) . ? O30 C31 1.415(3) . ? O30 C34 1.414(3) . ? C31 C32 1.444(4) . ? C32 C33 1.486(4) . ? C33 C34 1.471(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 O30 Li1 N1 108.61(18) . 3_655 ? O30 Li1 C8 116.30(17) . . ? N1 Li1 C8 116.14(17) 3_655 . ? O30 Li1 C8 112.49(17) . 3_655 ? N1 Li1 C8 82.04(14) 3_655 3_655 ? C8 Li1 C8 116.38(15) . 3_655 ? O30 Li1 Li1 141.5(3) . 3_655 ? N1 Li1 Li1 106.5(2) 3_655 3_655 ? C8 Li1 Li1 58.53(15) . 3_655 ? C8 Li1 Li1 57.86(15) 3_655 3_655 ? O30 Li1 C7 107.21(15) . . ? N1 Li1 C7 95.45(14) 3_655 . ? C8 Li1 C7 30.25(8) . . ? C8 Li1 C7 138.87(16) 3_655 . ? Li1 Li1 C7 84.29(18) 3_655 . ? O30 Li1 C1 96.97(15) . 3_655 ? N1 Li1 C1 30.98(8) 3_655 3_655 ? C8 Li1 C1 142.76(17) . 3_655 ? C8 Li1 C1 59.14(10) 3_655 3_655 ? Li1 Li1 C1 105.3(2) 3_655 3_655 ? C7 Li1 C1 126.41(15) . 3_655 ? C1 N1 C21 113.88(17) . . ? C1 N1 C22 111.01(15) . . ? C21 N1 C22 109.24(18) . . ? C1 N1 Li1 100.58(15) . 3_655 ? C21 N1 Li1 114.81(16) . 3_655 ? C22 N1 Li1 106.91(16) . 3_655 ? C2 C1 C9 121.1(2) . . ? C2 C1 N1 121.6(2) . . ? C9 C1 N1 117.27(17) . . ? C2 C1 Li1 149.33(16) . 3_655 ? C9 C1 Li1 76.42(14) . 3_655 ? N1 C1 Li1 48.44(12) . 3_655 ? C1 C2 C3 120.8(2) . . ? C4 C3 C2 120.2(2) . . ? C3 C4 C10 121.1(2) . . ? C6 C5 C10 120.5(2) . . ? C5 C6 C7 119.6(2) . . ? C8 C7 C6 125.4(2) . . ? C8 C7 Li1 53.15(13) . . ? C6 C7 Li1 168.80(18) . . ? C7 C8 C9 113.35(18) . . ? C7 C8 Li1 96.61(17) . . ? C9 C8 Li1 147.02(18) . . ? C7 C8 Li1 141.20(18) . 3_655 ? C9 C8 Li1 97.15(16) . 3_655 ? Li1 C8 Li1 63.62(15) . 3_655 ? C1 C9 C10 116.58(19) . . ? C1 C9 C8 120.87(18) . . ? C10 C9 C8 122.54(19) . . ? C5 C10 C4 121.5(2) . . ? C5 C10 C9 118.4(2) . . ? C4 C10 C9 120.1(2) . . ? C31 O30 C34 108.7(2) . . ? C31 O30 Li1 123.99(18) . . ? C34 O30 Li1 126.74(18) . . ? O30 C31 C32 108.5(3) . . ? C31 C32 C33 106.1(2) . . ? C34 C33 C32 103.8(2) . . ? O30 C34 C33 107.5(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.343 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.043