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_4120755
_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         'C36 H54 Li2 N2 O Si2'
_chemical_formula_sum            'C36 H54 Li2 N2 O Si2'
_chemical_formula_weight         600.87
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.9876(1)
_cell_length_b                   21.0189(2)
_cell_length_c                   25.6451(2)
_cell_measurement_reflns_used    81767
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     7539.76(11)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        HKL2000
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            85295
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.059
_exptl_crystal_description       block
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6814
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+2.9197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                5415
_reflns_number_total             6814
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja402884y_si_002_1.cif
_cod_data_source_block           s2685a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constrained' was replaced with
the value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               4120755