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_1501993
_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         'C50 H35 N'
_chemical_formula_sum            'C50 H35 N'
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_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.518(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0408(8)
_cell_length_b                   11.9207(10)
_cell_length_c                   25.282(2)
_cell_measurement_reflns_used    2793
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      53.074
_cell_measurement_theta_min      4.711
_cell_volume                     3605.4(5)
_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  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32372
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         8695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.1610
_refine_ls_R_factor_gt           0.0594
_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^)+(0.0533P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                4033
_reflns_number_total             8695
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol2000183_si_002.cif
_cod_data_source_block           is_pe314
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1501993