Mechanistic features of the copper-free Sonogashira reaction from ESI-MS.
Ahmadi, Zohrab; Yunker, Lars P. E.; Oliver, Allen G.; McIndoe, J. Scott; Dalton transactions (Cambridge, England : 2003) 44 (2015) 20367–20375; doi:10.1039/c5dt02889b

data_7036775
_publ_section_title
;
 Mechanistic features of the copper-free Sonogashira reaction from ESI-MS.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              20367
_journal_page_last               20375
_journal_paper_doi               10.1039/c5dt02889b
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C33 H26 P, F6 P, 0.5(C H4 O)'
_chemical_formula_sum            'C33.5 H28 F6 O0.5 P2'
_chemical_formula_weight         614.50
_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
_audit_update_record
;
2015-07-27 deposited with the CCDC.
2015-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.581(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7820(12)
_cell_length_b                   15.0655(19)
_cell_length_c                   20.388(3)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.43
_cell_volume                     2962.7(7)
_computing_cell_refinement       'Bruker SAINT v7.66A'
_computing_data_collection       'Bruker APEX-II v2010-7'
_computing_data_reduction        'Bruker SAINT v7.66A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39492
_diffrn_reflns_theta_full        26.56
_diffrn_reflns_theta_max         26.56
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0407P)^2^+1.5239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                5112
_reflns_number_total             6151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt02889b2.cif
_cod_data_source_block           jsm20a
_cod_depositor_comments          'Adding full bibliography for 7036775.cif.'
_cod_original_cell_volume        2962.7(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        'C33.50 H28 F6 O0.50 P2'
_cod_database_code               7036775