Supplementary Material (ESI) for Dalton Transactions
This journal is (c) The Royal Society of Chemistry 2001


data_([1-(Dimethylamino)-8-naphthyl]lithiumTHF)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]lithiumTHF)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 




