Iridium-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Isocyanates
Gen Onodera; Mari Suto; Ryo Takeuchi; Journal of Organic Chemistry 77 (2012) 908–920; doi:10.1021/jo202083z

data_4026891
_publ_section_title
;
 Iridium-Catalyzed [2+2+2] Cycloaddition of \a,\w-Diynes with Isocyanates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              908
_journal_page_last               920
_journal_paper_doi               10.1021/jo202083z
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 N O6'
_chemical_formula_sum            'C21 H23 N O6'
_chemical_formula_weight         385.42
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_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.302(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   13.9836(3)
_cell_length_b                   8.26140(15)
_cell_length_c                   17.9670(4)
_cell_measurement_reflns_used    23783
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.20
_cell_volume                     2048.33(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24560
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             816.00
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.205
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.200
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3335 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     513
_refine_ls_number_reflns         7338
_refine_ls_number_restraints     511
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.1353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                7036
_reflns_number_total             7338
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo202083z_si_004.cif
_cod_data_source_block           sc0917
_cod_database_code               4026891