Selective Formation of Adjacent Stereocenters by Allylboration of Ketones under Mild Neutral Conditions
Alam, Rauful; Raducan, Mihai,; Eriksson, Lars; Szabó, Kálmán J.; Organic Letters 15 (2013) 2546–; doi:10.1021/ol401055m

data_1512087
_publ_section_title
;
 Selective Formation of Adjacent Stereocenters by Allylboration of Ketones
 under Mild Neutral Conditions
;
_journal_issue                   10
_journal_name_full               'Organic Letters'
_journal_page_first              2546
_journal_paper_doi               10.1021/ol401055m
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C13 H20 O3'
_chemical_formula_weight         224.29
_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            8
_cell_length_a                   6.0852(2)
_cell_length_b                   11.7873(4)
_cell_length_c                   35.4794(12)
_cell_measurement_temperature    293(2)
_cell_volume                     2544.87(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            45672
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.240
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0487P)^2^+0.6951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                4355
_reflns_number_total             4489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401055m_si_004.cif
_cod_data_source_block           r
_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 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2544.89(15)
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               1512087