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_4120757
_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         'C39 H43 Li2 N3'
_chemical_formula_sum            'C39 H43 Li2 N3'
_chemical_formula_weight         567.64
_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                61.592(3)
_cell_angle_beta                 72.660(2)
_cell_angle_gamma                81.328(3)
_cell_formula_units_Z            2
_cell_length_a                   11.8142(7)
_cell_length_b                   12.8038(7)
_cell_length_c                   13.1046(7)
_cell_measurement_reflns_used    12889
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.81
_cell_volume                     1664.25(17)
_computing_cell_refinement       Peakref
_computing_data_collection       Apex2
_computing_data_reduction        'Eval15, SADABS-2008/1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24549
_diffrn_reflns_theta_full        25.74
_diffrn_reflns_theta_max         25.74
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.4419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1300
_reflns_number_gt                3910
_reflns_number_total             6350
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja402884y_si_002_3.cif
_cod_data_source_block           l0393a
_cod_database_code               4120757