Palladium-Catalyzed N-Acylation of Monosubstituted Ureas Using Near-Stoichiometric Carbon Monoxide
Klaus Bjerglund; Anders T. Lindhardt; Troels Skrydstrup; Journal of Organic Chemistry 77 (2012) 3793–3799; doi:10.1021/jo3000767

data_4027151
_publ_contact_author_address
;
Department of Chemistry
Aarhus University
Langelandsgade 140
DK-8000 Aarhus C
;
_publ_contact_author_email       jacobo@chem.au.dk
_publ_contact_author_fax         '+45 8619 6199'
_publ_contact_author_name        'Overgaard, Jacob'
_publ_contact_author_phone       '+45 8942 3891'
_publ_section_title
;
 Palladium-Catalyzed N-Acylation of Monosubstituted Ureas Using
 Near-Stoichiometric Carbon Monoxide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3793
_journal_page_last               3799
_journal_paper_doi               10.1021/jo3000767
_journal_volume                  77
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-11-21T09:06:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.237(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7361(8)
_cell_length_b                   6.3813(5)
_cell_length_c                   17.5262(14)
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      2.4
_cell_measurement_wavelength     0.71073
_cell_volume                     1272.25(17)
_computing_cell_refinement       'Saint+ v7.68A (Bruker-Nonius, 2011)'
_computing_data_collection       'Apex2 v2011(Bruker-Nonius, 2011)'
_computing_data_reduction        'Saint+ v7.68A (Bruker-Nonius, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 12.00
_diffrn_detector_type            'APEX2 charged-coupled device'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method
;
            Narrow slices collected using \f-scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.052
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5091
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       rod
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.3540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                1706
_reflns_number_total             2475
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo3000767_si_002.cif
_cod_data_source_block           11jo0029a_01
_cod_database_code               4027151