A Palladium Iodide-Catalyzed Carbonylative Approach to Functionalized Pyrrole Derivatives
Bartolo Gabriele; Lucia Veltri; Raffaella Mancuso; Giuseppe Salerno; Sabino Maggi; Brunella Maria Aresta; Journal of Organic Chemistry 77 (2012) 4005–4016; doi:10.1021/jo300365n

data_4027160
_publ_contact_author_address
;
 Dipartimento di Scienze Farmaceutiche
 Universit\`a della Calabria
 I-87036 Arcavacata di Rende (CS), Italy
;
_publ_contact_author_email       b.gabriele@unical.it
_publ_contact_author_fax         '+39 0984 492044'
_publ_contact_author_name        'Bartolo Gabriele'
_publ_contact_author_phone       '+39 0984 492813'
_publ_section_title
;
 A Palladium Iodide-Catalyzed Carbonylative Approach to Functionalized
 Pyrrole Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4005
_journal_page_last               4016
_journal_paper_doi               10.1021/jo300365n
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H29 N O3'
_chemical_formula_sum            'C16 H29 N O3'
_chemical_formula_weight         283.40
_chemical_name_common            syn-3f_diastereomer
_chemical_name_systematic
;
(3RS,4RS)-N-Boc-3-amino-2-methyldec-5-yn-4-ol
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-10
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.94(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.252(4)
_cell_length_b                   19.841(9)
_cell_length_c                   15.137(4)
_cell_measurement_reflns_used    125
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      5.0
_cell_volume                     3644(2)
_computing_cell_refinement       'DIRAX (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'COLLECT (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'DENZO and SCALEPAK(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
'SIR2011 (Burla et al., accepted for publication in J.Appl.Cryst)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_measurement_specimen_support fiber
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1571
_diffrn_reflns_av_sigmaI/netI    0.1060
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21075
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         5.04
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0836 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.8400.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.033
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         4105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1932
_refine_ls_R_factor_gt           0.0746
_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^)+(0.0743P)^2^+1.1721P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1969
_reflns_number_gt                1762
_reflns_number_total             4105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300365n_si_002.cif
_cod_data_source_block           syn-3f_diastereomer
_cod_database_code               4027160