Kinetic Resolution in a Bridgehead Lithiation Mediated by a Chiral Bis-lithium Amide: Assignment of the Absolute Configuration of Clusianone
Vincent Rodeschini; Nigel S. Simpkins; Claire Wilson; Journal of Organic Chemistry 72 (2007) 4265–4267; doi:10.1021/jo070225t

data_4022915
_publ_section_title
;
 Kinetic Resolution in a Bridgehead Lithiation Mediated by a Chiral
 Bis-lithium Amide: Assignment of the Absolute Configuration of Clusianone
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4265
_journal_page_last               4267
_journal_paper_doi               10.1021/jo070225t
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H39 Br O3'
_chemical_formula_weight         515.51
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   'geom, OH and sp2 bound Me from difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.166(1)
_cell_angle_beta                 82.396(1)
_cell_angle_gamma                64.257(1)
_cell_formula_units_Z            3
_cell_length_a                   10.5116(9)
_cell_length_b                   11.2613(10)
_cell_length_c                   19.5145(18)
_cell_measurement_reflns_used    6723
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      2.3
_cell_volume                     2034.1(3)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.009
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17426
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.542
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS v2.05'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.017(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     907
_refine_ls_number_reflns         15690
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0691P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                13753
_reflns_number_total             15690
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo070225tsi20070202_120258.cif
_cod_data_source_block           (+)12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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               4022915