Multiple sonogashira reactions of polychlorinated molecules. Synthesis and photophysical properties of the first pentaalkynylpyridines.
Ehlers, Peter; Neubauer, Antje; Lochbrunner, Stefan; Villinger, Alexander; Langer, Peter; Organic letters 13 (2011) 1618–1621; doi:10.1021/ol2000183

data_1501994
_publ_section_title
;
 Multiple sonogashira reactions of polychlorinated molecules. Synthesis
 and photophysical properties of the first pentaalkynylpyridines.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1618
_journal_page_last               1621
_journal_paper_doi               10.1021/ol2000183
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C60 H42'
_chemical_formula_sum            'C60 H42'
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_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      148
_symmetry_space_group_name_Hall  '-R 3'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   18.6752(12)
_cell_length_b                   18.6752(12)
_cell_length_c                   10.6107(9)
_cell_measurement_reflns_used    5444
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.683
_cell_measurement_theta_min      4.364
_cell_volume                     3204.8(4)
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_collection       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10847
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1206
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0877P)^2^+0.4852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1730
_reflns_number_total             2068
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol2000183_si_002.cif
_cod_data_source_block           is_pe305
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1501994