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_4026988
_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            'C24 H30 N2 O2 Pd'
_chemical_formula_weight         484.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8063(7)
_cell_length_b                   12.8761(10)
_cell_length_c                   19.9840(16)
_cell_measurement_reflns_used    984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.98
_cell_volume                     2266.0(3)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART1K CCD'
_diffrn_measurement_method       'phi and omega'
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25083
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  0.8050
_exptl_absorpt_correction_T_min  0.7690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            'yellow orange'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0160
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.4096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0419
_reflns_number_gt                5425
_reflns_number_total             5522
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2025724_si_001.cif
_cod_data_source_block           leo204
_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               4026988