Nickel-Catalyzed Cycloaddition of o-Arylcarboxybenzonitriles and Alkynes via Cleavage of Two Carbon-Carbon σ Bonds
Kenichiro Nakai; Takuya Kurahashi; Seijiro Matsubara; Journal of the American Chemical Society 133 (2011) 11066–11068; doi:10.1021/ja203829j

data_4106459
_publ_section_title
;
 Nickel-Catalyzed Cycloaddition of o-Arylcarboxybenzonitriles and Alkynes
 via Cleavage of Two Carbon-Carbon \s Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11066
_journal_page_last               11068
_journal_paper_doi               10.1021/ja203829j
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C15 H18 O2'
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_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 118.6190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.5116(7)
_cell_length_b                   32.412(3)
_cell_length_c                   9.5796(7)
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.48
_cell_volume                     2592.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
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_diffrn_reflns_theta_full        27.02
_diffrn_reflns_theta_max         27.02
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9272
_exptl_absorpt_correction_T_min  0.9272
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          1.00
_exptl_crystal_size_min          1.00
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0698
_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^)+(0.1034P)^2^+0.9032P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2057
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203829j_si_005.cif
_cod_data_source_block           19kn
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_cod_database_code               4106459