Iridium-Catalyzed [2 + 2 + 2] Cycloaddition of α,ω-Diynes with Nitriles
Gen Onodera; Yoshihisa Shimizu; Jun-na Kimura; Junya Kobayashi; Yukiko Ebihara; Kei Kondo; Ken Sakata; Ryo Takeuchi; Journal of the American Chemical Society 134 (2012) 10515–10531; doi:10.1021/ja3028394

data_4118122
_publ_section_title
;
 Iridium-Catalyzed [2 + 2 + 2] Cycloaddition of \a,\w-Diynes with Nitriles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10515
_journal_page_last               10531
_journal_paper_doi               10.1021/ja3028394
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C41 H37 N3 O8 S'
_chemical_formula_weight         731.80
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                66.910(3)
_cell_angle_beta                 81.911(3)
_cell_angle_gamma                79.155(3)
_cell_formula_units_Z            2
_cell_length_a                   11.676(2)
_cell_length_b                   11.698(2)
_cell_length_c                   14.139(3)
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    90
_cell_measurement_theta_max      22.09
_cell_measurement_theta_min      2.46
_cell_volume                     1740.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6900
_diffrn_reflns_theta_full        22.89
_diffrn_reflns_theta_max         22.89
_diffrn_reflns_theta_min         1.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_correction_T_min  0.9551
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.404
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          8.883
_refine_ls_shift/su_mean         0.037
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+3.5712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1686
_reflns_number_gt                3359
_reflns_number_total             4734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3028394_si_008.cif
_cod_data_source_block           ebi_5
_cod_original_cell_volume        1739.9(6)
_cod_database_code               4118122