Regioselective Orthopalladation of (Z)-2-Aryl-4-Arylidene-5(4H)-Oxazolones: Scope, Kinetico-Mechanistic, and Density Functional Theory Studies of the C-H Bond Activation
Gheorghe-Doru Roiban; Elena Serrano; Tatiana Soler; Gabriel Aullón; Ion Grosu; Carlos Cativiela; Manuel Martínez; Esteban P. Urriolabeitia; Inorganic Chemistry 50 (2011) 8132–8143; doi:10.1021/ic200564d

data_4326018
_publ_contact_author_address
;
ICMA, CSIC-Universidad de Zaragoza, 
Plaza S. Francisco, 50009 Zaragoza (Spain)
;
_publ_contact_author_email       esteban@unizar.es
_publ_contact_author_fax         (+34)976761187
_publ_contact_author_name        'Esteban P. Urriolabeitia'
_publ_contact_author_phone       (+34)976762302
_publ_section_title
;
 Regioselective Orthopalladation of
 (Z)-2-Aryl-4-Arylidene-5(4H)-Oxazolones: Scope, Kinetico-Mechanistic, and
 Density Functional Theory Studies of the C-H Bond Activation
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8132
_journal_page_last               8143
_journal_paper_doi               10.1021/ic200564d
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C20 H14 F3 N O6 Pd, 0.25(C H2 Cl2)'
_chemical_formula_sum            'C20.25 H14.5 Cl0.5 F3 N O6 Pd'
_chemical_formula_weight         548.95
_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                106.424(3)
_cell_angle_beta                 101.629(2)
_cell_angle_gamma                110.283(3)
_cell_formula_units_Z            8
_cell_length_a                   15.5086(4)
_cell_length_b                   16.1894(6)
_cell_length_c                   19.0450(6)
_cell_measurement_reflns_used    23571
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      28.8633
_cell_measurement_theta_min      2.7896
_cell_volume                     4056.7(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_molecular_graphics
;
SHELXTL  Rel. 6.12/V (Sheldrick, Acta Cryst. 2008, A64, 112-122)
;
_computing_publication_material
;
SHELX-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122)' 
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122) 
;
_computing_structure_solution
;
SHELXL-97 (Sheldrick, Acta Cryst. 2008, A64, 112-122) 
;
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            65791
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_T_max  0.9006
_exptl_absorpt_correction_T_min  0.8638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_description       block
_exptl_crystal_F_000             2180
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1235
_refine_ls_number_reflns         14266
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0124P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0478
_reflns_number_gt                10202
_reflns_number_total             14266
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ic200564d_si_003_1.cif
_cod_data_source_block           '__5i'
_cod_original_cell_volume        4056.7(2)
_cod_original_formula_sum        'C20.25 H14.50 Cl0.50 F3 N O6 Pd'
_cod_database_code               4326018