Structure and Reactivity of a Preactivated sp2-sp3 Diboron Reagent: Catalytic Regioselective Boration of α,β-Unsaturated Conjugated Compounds
Ming Gao; Steven B. Thorpe; Christian Kleeberg; Carla Slebodnick; Todd B. Marder; Webster L. Santos; Journal of Organic Chemistry 76 (2011) 3997–4007; doi:10.1021/jo2003488

data_4026299
_publ_contact_author_address
;
 Department of Chemistry 
   Virginia Tech 
   3101 Hahn Hall
   West campus Dr. 
   Blacksburg, VA  24061  USA
;
_publ_contact_author_email       wsantos@vt.edu
_publ_contact_author_fax         1(540)2313255
_publ_contact_author_name        'Webster L. Santos'
_publ_contact_author_phone       1(540)2315742
_publ_section_title
;
 Structure and Reactivity of a Preactivated sp2-sp3 Diboron Reagent:
 Catalytic Regioselective Boration of \a,\b-Unsaturated Conjugated
 Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3997
_journal_page_last               4007
_journal_paper_doi               10.1021/jo2003488
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H25 B2 N O4'
_chemical_formula_sum            'C12 H25 B2 N O4'
_chemical_formula_weight         268.95
_chemical_name_common
;
(R,R)-PDIPA diboron 
;
_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                   9.5436(2)
_cell_length_b                   11.7206(3)
_cell_length_c                   13.6397(3)
_cell_measurement_reflns_used    8058
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.1065
_cell_measurement_theta_min      3.7634
_cell_volume                     1525.69(6)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_publication_material
'SHELXTL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_computing_structure_solution
'SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.0122
_diffrn_detector_type            'Oxford Diffraction Eos'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      0.1278711553
_diffrn_orient_matrix_UB_12      0.0433610912
_diffrn_orient_matrix_UB_13      0.0580670918
_diffrn_orient_matrix_UB_21      -0.0267481693
_diffrn_orient_matrix_UB_22      0.1216076086
_diffrn_orient_matrix_UB_23      -0.0379724187
_diffrn_orient_matrix_UB_31      -0.0948256119
_diffrn_orient_matrix_UB_32      0.0237413125
_diffrn_orient_matrix_UB_33      0.0890635929
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9951
_diffrn_reflns_theta_full        72.25
_diffrn_reflns_theta_max         72.25
_diffrn_reflns_theta_min         4.98
_diffrn_source                   'Nova (Cu) X-ray Source'
_diffrn_source_current           1
_diffrn_source_voltage           50
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro, v171.33.41, 2009'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       rod
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0551P)^2^+0.3437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                2853
_reflns_number_total             2992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2003488_si_003.cif
_cod_data_source_block           cs1343
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_database_code               4026299