A new mechanistic pathway under Sonogashira reaction protocol involving multiple acetylene insertions.
Jones, Roderick C.; Canty, Allan J.; Caradoc-Davies, Tom; Davies, Noel W.; Gardiner, Michael G.; Marriott, Philip J.; Rühle, Christian P G; Tolhurst, Vicki-Anne; Dalton transactions (Cambridge, England : 2003) 39 (2010) 3799–3801; doi:10.1039/c001109f

data_7025468
_publ_section_title
;
 A new mechanistic pathway under Sonogashira reaction protocol involving
 multiple acetylene insertions.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3799
_journal_page_last               3801
_journal_paper_doi               10.1039/c001109f
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety         'C13 H13 I N2 O2 Pd S'
_chemical_formula_sum            'C13 H13 I N2 O2 Pd S'
_chemical_formula_weight         494.61
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 95.476(6)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   7.7510(10)
_cell_length_b                   11.9940(13)
_cell_length_c                   16.0450(12)
_cell_measurement_reflns_used    14568
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.32
_cell_volume                     1484.8(3)
_computing_cell_refinement       XDS
_computing_data_collection       BLU-ICE
_computing_data_reduction        XDS
_computing_molecular_graphics
;
'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)'
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 'ADSC Q210'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       Rotation
_diffrn_radiation_monochromator  Si<111>
_diffrn_radiation_source         'synchrotron BM'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.77487
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_sigmaI/netI    0.0592
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_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15675
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    3.471
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
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_exptl_crystal_size_mid          0.03
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_refine_diff_density_max         0.748
_refine_diff_density_min         -1.497
_refine_diff_density_rms         0.184
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+5.6246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
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_reflns_number_gt                2190
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_reflns_threshold_expression     >2sigma(I)
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_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7025468