Preparation of Chiral α-Oxy-[2H1]methyllithiums of 99% ee and Determination of Their Configurational Stability
Dagmar Kapeller; Roland Barth; Kurt Mereiter; Friedrich Hammerschmidt; Journal of the American Chemical Society 129 (2007) 914–923; doi:10.1021/ja066183s

data_4109019
_publ_contact_author
;
Friedrich Hammerschmidt
Institut f\"ur Organische Chemie der Universit\"at Wien
W\"ahringerstrasse 38
A-1090 Wien
Austria
phone: ++ 43 - 1 - 4277 - 52105 or 52138
fax: ++ 43 - 1 - 4277 - 9521
E-mail: friedrich.hammerschmidt@univie.ac.at
;
_publ_contact_author_email       friedrich.hammerschmidt@univie.ac.at
_publ_contact_author_fax         '++ 43 - 1 - 4277 - 9521'
_publ_contact_author_phone       '++ 43 - 1 - 4277 - 52105 or 52138'
_publ_section_title
;
 Preparation of Chiral \a-Oxy-[2H1]methyllithiums of 99% ee and
 Determination of Their Configurational Stability
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              914
_journal_page_last               923
_journal_paper_doi               10.1021/ja066183s
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H68 B N O4 Sn'
_chemical_formula_sum            'C37 H68 B N O4 Sn'
_chemical_formula_weight         720.42
_chemical_name_common            '1002FH ZH-760 C37H67BNO4Sn chiral xx1'
_chemical_name_systematic
; 
 ? 
;
_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                   12.6228(5)
_cell_length_b                   15.3039(6)
_cell_length_c                   20.0687(8)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      2.32
_cell_volume                     3876.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT, SADABS, XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            58095
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.795
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'program SADABS, V2.10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 5087 Friedel pairs measured'
_refine_ls_abs_structure_Flack   -0.021(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         11299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0165
_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^)+(0.0243P)^2^+0.3837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0424
_reflns_number_gt                11043
_reflns_number_total             11299
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja066183ssi20060825_091550.cif
_cod_data_source_block           compd50
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4109019