A Rational Protocol for the Synthesis of Arylated Bipyridine Ligands via a Cycloaddition Pathway
Stéphane Diring; Pascal Retailleau; Raymond Ziessel; Journal of Organic Chemistry 72 (2007) 10181–10193; doi:10.1021/jo7019866

data_4023139
_publ_section_title
;
 A Rational Protocol for the Synthesis of Arylated Bipyridine
 Ligands via a Cycloaddition Pathway
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10181
_journal_page_last               10193
_journal_paper_doi               10.1021/jo7019866
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C44 H54 N4'
_chemical_formula_sum            'C44 H54 N4'
_chemical_formula_weight         638.91
_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
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 107.245(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   15.161(5)
_cell_length_b                   25.720(5)
_cell_length_c                   10.503(5)
_cell_measurement_reflns_used    3187
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.848
_cell_measurement_theta_min      0.407
_cell_volume                     3911(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .992
_diffrn_measured_fraction_theta_max .992
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23064
_diffrn_reflns_theta_full        18.91
_diffrn_reflns_theta_max         18.91
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack,(Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         .320
_refine_diff_density_min         -.235
_refine_diff_density_rms         .044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     275
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0830
_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^)+(0.1920P)^2^+0.7070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2397
_refine_ls_wR_factor_ref         0.2815
_reflns_number_gt                1926
_reflns_number_total             3085
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7019866-File003.cif
_cod_data_source_block           compound_13_sd177
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023139