Cyclization by Intramolecular Carbolithiation of Alkyl- and Vinyllithiums Prepared by the Action of Aromatic Radical Anions on Phenyl Thioethers. High Stereoselectivity in the Cyclization Accelerated by an Allylic Lithium Oxyanion
Kai Deng; Ahlem Bensari-Bouguerra; Joseph Whetstone; Theodore Cohen; Journal of Organic Chemistry 71 (2006) 2360–2372; doi:10.1021/jo052535m

data_4021571
_publ_section_title
;
 Cyclization by Intramolecular Carbolithiation of Alkyl- and Vinyllithiums
 Prepared by the Action of Aromatic Radical Anions on Phenyl
 Thioethers. High Stereoselectivity in the Cyclization Accelerated by
 an Allylic Lithium Oxyanion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2360
_journal_page_last               2372
_journal_paper_doi               10.1021/jo052535m
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C12 H22 O'
_chemical_formula_weight         182.30
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_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            16
_cell_length_a                   9.1390(14)
_cell_length_b                   19.074(4)
_cell_length_c                   26.460(4)
_cell_measurement_temperature    295(2)
_cell_volume                     4612.5(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1105
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17733
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.050
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                1442
_reflns_number_total             2087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo052535mrom20051209_102322.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4021571