Enantioselective Carbonyl Reverse Prenylation from the Alcohol or Aldehyde Oxidation Level Employing 1,1-Dimethylallene as the Prenyl Donor
Soo Bong Han; In Su Kim; Hoon Han; Michael J. Krische; Journal of the American Chemical Society 131 (2009) 6916–6917; doi:10.1021/ja902437k

data_4104420
_publ_section_title
;
 Enantioselective Carbonyl Reverse Prenylation from the Alcohol or
 Aldehyde Oxidation Level Employing 1,1-Dimethylallene as the Prenyl Donor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6916
_journal_page_last               6917
_journal_paper_doi               10.1021/ja902437k
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety
'C38 H28 O4 P2, C7 H3 N O4, C3 H5,  C4 H10 O, Ir'
_chemical_formula_sum            'C52 H46 Ir N O9 P2'
_chemical_formula_weight         1083.04
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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            8
_cell_length_a                   22.8055(12)
_cell_length_b                   23.0389(12)
_cell_length_c                   17.2256(9)
_cell_measurement_reflns_used    10337
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     9050.6(8)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1117
_diffrn_reflns_av_sigmaI/netI    0.1070
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            56129
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    3.081
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.560
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(see. N.W. Alcock (1970). Cryst. Computing, p271)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             4352
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_refine_diff_density_max         3.234
_refine_diff_density_min         -2.797
_refine_diff_density_rms         0.212
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.033(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.769
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     1082
_refine_ls_number_reflns         15676
_refine_ls_number_restraints     720
_refine_ls_restrained_S_all      1.758
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0809
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+4.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                12455
_reflns_number_total             15676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja902437k_si_002.cif
_cod_data_source_block           hhsese1
_cod_database_code               4104420