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_1508007
_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_absolute_configuration syn
_chemical_formula_moiety         'C17 H26 O'
_chemical_formula_sum            'C17 H26 O'
_chemical_formula_weight         246.388
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_block_code                C17H26O_ln549_knochel
_audit_creation_date             09-Oct-07
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             15-Oct-07
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5955(2)
_cell_length_b                   7.8820(2)
_cell_length_c                   29.1769(8)
_cell_measurement_reflns_used    30768
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.134
_cell_volume                     1516.78(7)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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      -0.0002403
_diffrn_orient_matrix_UB_12      0.1098174
_diffrn_orient_matrix_UB_13      -0.0171631
_diffrn_orient_matrix_UB_21      -0.1395401
_diffrn_orient_matrix_UB_22      0.0246891
_diffrn_orient_matrix_UB_23      0.0116284
_diffrn_orient_matrix_UB_31      0.0593016
_diffrn_orient_matrix_UB_32      0.0585399
_diffrn_orient_matrix_UB_33      0.0272927
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10226
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         3.17
_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    0.064
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.07898(5)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0514P)^2^+0.1045P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                1415
_reflns_number_total             1748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.505-s2.cif
_cod_data_source_block           ln549
_cod_database_code               1508007