Highly diastereoselective addition of cinnamylzinc derivatives to alpha-chiral carbonyl compounds.
Dunet, Guillaume; Mayer, Peter; Knochel, Paul; Organic letters 10 (2008) 117–120; doi:10.1021/ol702607t

data_1504487
_publ_section_title
;
 Highly diastereoselective addition of cinnamylzinc derivatives to
 alpha-chiral carbonyl compounds.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              117
_journal_page_last               120
_journal_paper_doi               10.1021/ol702607t
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C22 H26 O2'
_chemical_formula_sum            'C22 H26 O2'
_chemical_formula_weight         322.441
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C22H26O2_ln147_knochel
_audit_creation_date             22-Mar-07
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             16-Oct-07
_cell_angle_alpha                90.00
_cell_angle_beta                 97.6503(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1290(3)
_cell_length_b                   5.8900(2)
_cell_length_c                   27.1429(7)
_cell_measurement_reflns_used    50578
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.134
_cell_volume                     1763.38(9)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0078078
_diffrn_orient_matrix_UB_12      -0.0538883
_diffrn_orient_matrix_UB_13      -0.0352188
_diffrn_orient_matrix_UB_21      -0.0299318
_diffrn_orient_matrix_UB_22      0.1533834
_diffrn_orient_matrix_UB_23      -0.0117113
_diffrn_orient_matrix_UB_31      0.0852219
_diffrn_orient_matrix_UB_32      0.0489346
_diffrn_orient_matrix_UB_33      -0.0020753
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6222
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         3.54
_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    1.21456(6)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0464P)^2^+0.4460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                2598
_reflns_number_total             3449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702607t-file004.cif
_cod_data_source_block           ln147
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1504487