Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide.
Chen, Jianbin; Natte, Kishore; Spannenberg, Anke; Neumann, Helfried; Beller, Matthias; Wu, Xiao-Feng; Organic & biomolecular chemistry 12 (2014) 5578–5581; doi:10.1039/c4ob00796d

data_7153795
_publ_section_title
;
 Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes:
 synthesis of thalidomide.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5578
_journal_page_last               5581
_journal_paper_doi               10.1039/c4ob00796d
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.290(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9282(5)
_cell_length_b                   13.3172(6)
_cell_length_c                   6.6540(3)
_cell_measurement_reflns_used    4277
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      3.06
_cell_volume                     1119.35(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15678
_diffrn_reflns_theta_full        28.85
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.4257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                2185
_reflns_number_total             2926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00796d2.cif
_cod_data_source_block           ax0508
_cod_depositor_comments          'Adding full bibliography for 7153795.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153795