Enantioselective Carbonyl Allylation, Crotylation, and tert-Prenylation of Furan Methanols and Furfurals via Iridium-Catalyzed Transfer Hydrogenation
Benjamin Bechem; Ryan L. Patman; A. Stephen K. Hashmi; Michael J. Krische; Journal of Organic Chemistry 75 (2010) 1795–1798; doi:10.1021/jo902697g

data_4025281
_publ_section_title
;
 Enantioselective Carbonyl Allylation, Crotylation, and tert-Prenylation
 of Furan Methanols and Furfurals via Iridium-Catalyzed Transfer
 Hydrogenation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1795
_journal_page_last               1798
_journal_paper_doi               10.1021/jo902697g
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety
'C36 H28 P2, C3 H5, C7 H3 N O4, Ir, 2 C H2 Cl2'
_chemical_formula_sum            'C48 H40 Cl4 Ir N O4 P2'
_chemical_formula_weight         1090.75
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.815(2)
_cell_angle_beta                 110.995(3)
_cell_angle_gamma                97.873(3)
_cell_formula_units_Z            2
_cell_length_a                   12.7104(15)
_cell_length_b                   13.594(2)
_cell_length_c                   13.826(2)
_cell_measurement_reflns_used    23357
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     2179.9(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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      233(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCX-Mini'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            23357
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    3.428
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor.  T. Higashi.  (2001).  Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.994
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         10012
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+3.3498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                9224
_reflns_number_total             10012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902697g_si_001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025281