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_4023140
_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         'C16 H10 Cl I N2 Pt'
_chemical_formula_sum            'C16 H10 Cl I N2 Pt'
_chemical_formula_weight         587.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.169(1)
_cell_length_b                   12.543(2)
_cell_length_c                   14.364(2)
_cell_measurement_reflns_used    3391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_cell_volume                     1471.9(4)
_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 .985
_diffrn_measured_fraction_theta_max .985
_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     0.71070
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15790
_diffrn_reflns_theta_full        27.68
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    11.805
_exptl_absorpt_correction_T_max  0.310
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL SCALEPACK, Blessing'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.048
_refine_diff_density_min         -1.482
_refine_diff_density_rms         .159
_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     190
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+3.5587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                2131
_reflns_number_total             3184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7019866-File004.cif
_cod_data_source_block           compound_23_sd114
_cod_database_code               4023140