Palladium-Catalyzed Double Carbonylation Using Near Stoichiometric Carbon Monoxide: Expedient Access to Substituted 13C2-Labeled Phenethylamines
Dennis U. Nielsen; Karoline Neumann; Rolf H. Taaning; Anders T. Lindhardt; Amalie Modvig; Troels Skrydstrup; Journal of Organic Chemistry 77 (2012) 6155–6165; doi:10.1021/jo3009337

data_4027326
_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 Double Carbonylation Using Near Stoichiometric Carbon
 Monoxide: Expedient Access to Substituted 13C2-Labeled Phenethylamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6155
_journal_page_last               6165
_journal_paper_doi               10.1021/jo3009337
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2011-11-17
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  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.066(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3286(3)
_cell_length_b                   10.3522(2)
_cell_length_c                   10.2050(2)
_cell_measurement_reflns_used    9276
_cell_measurement_temperature    250.01(11)
_cell_measurement_theta_max      28.6041
_cell_measurement_theta_min      1.6577
_cell_volume                     1295.15(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      250.01(11)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details
;
  1 omega  -70.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337  -19.0000    0.0000 181

  2 omega   35.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  178.0000  150.0000 33

  3 omega  -75.00  113.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337   19.0000  150.0000 188

  4 omega   34.00  118.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337 -178.0000  120.0000 84

  5 omega  -20.00   31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  -99.0000  -90.0000 51

  6 omega  -20.00   31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  -99.0000 -150.0000 51

  7 omega   35.00   81.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931  178.0000  -30.0000 46

  8 omega  -61.00   72.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6931   57.0000  -90.0000 133

  9 omega  -28.00   39.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337   38.0000  -90.0000 67

 10 omega   34.00  118.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8337 -178.0000  -90.0000 84
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_UB_11      0.0084886000
_diffrn_orient_matrix_UB_12      0.0042135000
_diffrn_orient_matrix_UB_13      -0.0675378000
_diffrn_orient_matrix_UB_21      -0.0495866000
_diffrn_orient_matrix_UB_22      0.0346630000
_diffrn_orient_matrix_UB_23      -0.0129761000
_diffrn_orient_matrix_UB_31      0.0285076000
_diffrn_orient_matrix_UB_32      0.0590115000
_diffrn_orient_matrix_UB_33      0.0123638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20601
_diffrn_reflns_theta_full        28.67
_diffrn_reflns_theta_max         28.67
_diffrn_reflns_theta_min         1.66
_diffrn_source                   ' 'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.4293
_exptl_crystal_size_min          0.3241
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0447P)^2^+0.1986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2453
_reflns_number_total             3161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3009337_si_002.cif
_cod_data_source_block           11jo0022s
_cod_original_cell_volume        1295.16(5)
_cod_database_code               4027326
_chemical_oxdiff_formula         'C13 H17 N O3'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32