Intramolecular Vinylation of Secondary and Tertiary Organolithiums
Julien Lefranc; Anne M. Fournier; Gaëlle Mingat; Simon Herbert; Tommaso Marcelli; Jonathan Clayden; Journal of the American Chemical Society 134 (2012) 7286–7289; doi:10.1021/ja301591m

data_4117874
_publ_contact_author_address
; 
Department of Chemistry 
University of Manchester 
Manchester M13 9PL 
England  UK 
;
_publ_contact_author_email       jrtest@spec.ch.man.ac.uk
_publ_contact_author_fax         44(161)275-4734
_publ_contact_author_name        'Raftery, James'
_publ_contact_author_phone       44(161)275-4700
_publ_section_title
;
 Intramolecular Vinylation of Secondary and Tertiary Organolithiums
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7286
_journal_page_last               7289
_journal_paper_doi               10.1021/ja301591m
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H15 Cl2 N'
_chemical_formula_weight         232.14
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.7873(17)
_cell_length_b                   7.4504(18)
_cell_length_c                   24.010(6)
_cell_measurement_reflns_used    426
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      16.839
_cell_measurement_theta_min      2.862
_cell_volume                     1214.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1521
_diffrn_reflns_av_sigmaI/netI    0.1948
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8678
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.23(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0868
_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^)+(0.0034P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                1317
_reflns_number_total             2135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja301591m_si_002.cif
_cod_data_source_block           s3533m
_cod_database_code               4117874