Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols and 2,3-Disubstituted Cyclobutanones
Mahmud M. Hussain; Hongmei Li; Nusrah Hussain; Mercedes Ureña; Patrick J. Carroll; Patrick J. Walsh; Journal of the American Chemical Society 131 (2009) 6516–6524; doi:10.1021/ja900147s

data_4104337
_publ_section_title
;
 Applications of 1-Alkenyl-1,1-Heterobimetallics in the Stereoselective
 Synthesis of Cyclopropylboronate Esters, Trisubstituted Cyclopropanols
 and 2,3-Disubstituted Cyclobutanones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6516
_journal_page_last               6524
_journal_paper_doi               10.1021/ja900147s
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C15 H18 Cl F3 O2'
_chemical_formula_weight         322.74
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                   24.797(3)
_cell_length_b                   13.2290(12)
_cell_length_c                   9.6376(9)
_cell_measurement_temperature    143(1)
_cell_volume                     3161.5(6)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8807
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
   Shape function based on spherical harmonics.
   Highest even and odd order for spherical harmonics:  4  and  1
   Laue group:  mmm 
   Friedel opposites are equivalent.
;
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2786
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0806P)^2^+3.5809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                2263
_reflns_number_total             2786
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900147s_si_005.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        3161.6(5)
_cod_original_sg_symbol_H-M      'P b c n '
_cod_database_code               4104337