CuI-Catalyzed Conjugate Addition of Silyl Boronic Esters: Retracing Catalytic Cycles Using Isolated Copper and Boron Enolate Intermediates
Plotzitzka, Jacqueline; Kleeberg, Christian; Organometallics 33 (2014) 6915–; doi:10.1021/om500989w

data_4084813
_publ_section_title
;
 CuI-Catalyzed Conjugate Addition of Silyl Boronic Esters: Retracing
 Catalytic Cycles Using Isolated Copper and Boron Enolate Intermediates
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6915
_journal_paper_doi               10.1021/om500989w
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C39 H53 Cu N2 O Si'
_chemical_formula_sum            'C39 H53 Cu N2 O Si'
_chemical_formula_weight         657.46
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.354(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.256(3)
_cell_length_b                   14.9650(9)
_cell_length_c                   16.3670(13)
_cell_measurement_reflns_used    6880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      59.13
_cell_measurement_theta_min      4.02
_cell_volume                     8840.3(12)
_computing_cell_refinement
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
 (compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
 (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
 (compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
 Diamond 3.2i, K. Brandenburg, Crystal Impact GbR, Bonn, Germany.
;
_computing_publication_material
;
 WinGX v2013.2 (L. J. Farrugia, J. Appl. Cryst. 2012, 45, 849-854.)
;
_computing_structure_refinement
;
 SHELXL-2013 (G. M. Sheldrick, Acta Cryst. (2008), A64, 112 - 122)'
;
_computing_structure_solution
;
 SIR-92 (A. Altomare, G. Cascarano, C. Giacovazzo and A. Guagliardi,
 J. Appl. Crystallogr. 1993, 26, 343-350.)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction, Xcalibur, Atlas, Nova'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            76256
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         65.978
_diffrn_reflns_theta_min         4.038
_exptl_absorpt_coefficient_mu    1.143
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
 (compiled Dec 19 2012,11:08:27)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    0.988
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_platon_squeeze_details
;
 A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
;
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7685
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1597P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2178
_refine_ls_wR_factor_ref         0.2429
_reflns_number_gt                4892
_reflns_number_total             7685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500989w_si_002.cif
_cod_data_source_block           jp24ck
_cod_depositor_comments
'Adding full bibliography for 4084808--4084813.cif.'
_cod_original_cell_volume        8840.4(12)
_cod_database_code               4084813
_shelxl_version_number           2013-4
_shelx_res_checksum              74537
_shelx_hkl_checksum              36899