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_7025467
_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         'C30 H21 N O2'
_chemical_formula_sum            'C30 H21 N O2'
_chemical_formula_weight         427.48
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.032(11)
_cell_angle_beta                 77.218(13)
_cell_angle_gamma                66.155(17)
_cell_formula_units_Z            2
_cell_length_a                   10.588(4)
_cell_length_b                   10.867(5)
_cell_length_c                   10.920(4)
_cell_measurement_reflns_used    4953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      2.20
_cell_volume                     1119.7(8)
_computing_cell_refinement       XDS
_computing_data_collection       BLU-ICE
_computing_data_reduction        XDS
_computing_molecular_graphics
;
'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 2008)'
;
_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 Q315'
_diffrn_measured_fraction_theta_full 0.870
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  '3-ID1 Australian Synchrotron'
_diffrn_measurement_method       Rotation
_diffrn_radiation_monochromator  Si<111>
_diffrn_radiation_source         'Synchrotron ID'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.76207
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7122
_diffrn_reflns_theta_full        27.77
_diffrn_reflns_theta_max         27.77
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0913P)^2^+0.3139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                3084
_reflns_number_total             3728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c001109f.txt
_cod_data_source_block           c:\1-(4-nitrophenyl)-2,4,6-triphenylbenzene
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7025467