Palladacyclic Imidazoline-Naphthalene Complexes: Synthesis and Catalytic Performance in Pd(II)-Catalyzed Enantioselective Reactions of Allylic Trichloroacetimidates
Jeffrey S. Cannon; James H. Frederich; Larry E. Overman; Journal of Organic Chemistry 77 (2012) 1939–1951; doi:10.1021/jo2025724

data_4026989
_publ_section_title
;
 Palladacyclic Imidazoline-Naphthalene Complexes: Synthesis and Catalytic
 Performance in Pd(II)-Catalyzed Enantioselective Reactions of Allylic
 Trichloroacetimidates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1939
_journal_page_last               1951
_journal_paper_doi               10.1021/jo2025724
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H32 N2 O2 Pd'
_chemical_formula_weight         498.93
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2841(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.1379(12)
_cell_length_b                   7.2271(7)
_cell_length_c                   13.0990(13)
_cell_measurement_reflns_used    954
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      3.22
_cell_volume                     1142.16(19)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART1K CCD'
_diffrn_measurement_method       'phi and omega'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14328
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  0.8920
_exptl_absorpt_correction_T_min  0.7530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         5555
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0206
_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^)+(0.0345P)^2^+0.0484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0528
_reflns_number_gt                5367
_reflns_number_total             5555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2025724_si_002.cif
_cod_data_source_block           leo199
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap & geom' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               4026989