Synthetic Applications of Pd(II)-Catalyzed C-H Carboxylation and Mechanistic Insights: Expedient Routes to Anthranilic Acids, Oxazolinones, and Quinazolinones
Ramesh Giri; Jonathan K. Lam; Jin-Quan Yu; Journal of the American Chemical Society 132 (2010) 686–693; doi:10.1021/ja9077705

data_4101785
_publ_section_title
;
 Synthetic Applications of Pd(II)-Catalyzed C-H Carboxylation and
 Mechanistic Insights: Expedient Routes to Anthranilic Acids,
 Oxazolinones, and Quinazolinones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              686
_journal_page_last               693
_journal_paper_doi               10.1021/ja9077705
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C19 H22 N O5 Pd S'
_chemical_formula_weight         482.84
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 98.100(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   57.31(2)
_cell_length_b                   7.522(3)
_cell_length_c                   18.203(7)
_cell_measurement_reflns_used    9780
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.73
_cell_volume                     7769(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       68
_diffrn_reflns_limit_h_min       -68
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35679
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  0.8276
_exptl_absorpt_correction_T_min  0.7212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             3920
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.50(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1018
_refine_ls_number_reflns         10746
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0534P)^2^+28.1147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                10308
_reflns_number_total             10746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9077705_si_001.cif
_cod_data_source_block           yu13a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_cell_volume        7768(5)
_cod_database_code               4101785