Highly diastereoselective Csp₃-Csp₂ Negishi cross-coupling with 1,2-, 1,3- and 1,4-substituted cycloalkylzinc compounds.
Thaler, Tobias; Haag, Benjamin; Gavryushin, Andrei; Schober, Katrin; Hartmann, Evelyn; Gschwind, Ruth M.; Zipse, Hendrik; Mayer, Peter; Knochel, Paul; Nature chemistry 2 (2010) 125–130; doi:10.1038/nchem.505

data_1508008
_publ_section_title
;
 Highly diastereoselective Csp&#x2083;-Csp&#x2082; Negishi cross-coupling
 with 1,2-, 1,3- and 1,4-substituted cycloalkylzinc compounds.
;
_journal_issue                   2
_journal_name_full               'Nature chemistry'
_journal_page_first              125
_journal_page_last               130
_journal_paper_doi               10.1038/nchem.505
_journal_volume                  2
_journal_year                    2010
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.318
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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
_atom_sites_solution_secondary   difmap
_audit_block_code                C15H20O2_ln583_knochel
_audit_creation_date             24-Oct-07
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             20-Oct-09
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5673(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.7972(5)
_cell_length_b                   6.3827(2)
_cell_length_c                   26.2140(8)
_cell_measurement_reflns_used    27491
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.134
_cell_volume                     2625.78(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; omega-scans'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0019181
_diffrn_orient_matrix_UB_12      0.0863186
_diffrn_orient_matrix_UB_13      0.0319472
_diffrn_orient_matrix_UB_21      0.0636899
_diffrn_orient_matrix_UB_22      -0.0016362
_diffrn_orient_matrix_UB_23      0.0032766
_diffrn_orient_matrix_UB_31      -0.0004693
_diffrn_orient_matrix_UB_32      0.1307403
_diffrn_orient_matrix_UB_33      -0.0210515
_diffrn_radiation_collimation    0.20
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8464
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.18
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.17536(6)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0937P)^2^+0.7066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1739
_reflns_number_gt                1767
_reflns_number_total             2560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.505-s3.cif
_cod_data_source_block           ln583
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1508008