Directed ortho-Lithiation: Observation of an Unexpected 1-Lithio to 3-Lithio Conversion of 1-Lithio-naphthyllithium Compounds with an ortho-Directing 2-(Dimethylamino)methyl Group
Johann T. B. H. Jastrzebski; Anne M. Arink; Henk Kleijn; Thijs W. Braam; Martin Lutz; Anthony L. Spek; Gerard van Koten; Journal of the American Chemical Society 135 (2013) 13371–13378; doi:10.1021/ja402884y

data_4120756
_publ_contact_author_address
; Bijvoet Center for Biomolecular Research
  Crystal and Structural Chemistry
  Utrecht University
  Padualaan 8
  3584 CH Utrecht
  The Netherlands
;
_publ_contact_author_email       m.lutz@uu.nl
_publ_contact_author_fax         '[+31] 30 2533940'
_publ_contact_author_name        'Martin Lutz'
_publ_contact_author_phone       '[+31] 30 2533902'
_publ_section_title
;
 Directed ortho-Lithiation: Observation of an Unexpected 1-Lithio to
 3-Lithio Conversion of 1-Lithio-naphthyllithium Compounds with an
 ortho-Directing 2-(Dimethylamino)methyl Group
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13371
_journal_page_last               13378
_journal_paper_doi               10.1021/ja402884y
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C52 H56 Li4 N4'
_chemical_formula_sum            'C52 H56 Li4 N4'
_chemical_formula_weight         764.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.7660(6)
_cell_angle_beta                 96.1318(6)
_cell_angle_gamma                96.2745(6)
_cell_formula_units_Z            2
_cell_length_a                   10.5381(1)
_cell_length_b                   10.8025(2)
_cell_length_c                   20.0558(3)
_cell_measurement_reflns_used    43924
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     2241.88(6)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'HKL2000, SortAV'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36778
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.03
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light purple'
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         10208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.1397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                6931
_reflns_number_total             10208
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja402884y_si_002_2.cif
_cod_data_source_block           s3200a
_cod_database_code               4120756