Nickel-catalyzed [2 + 2 + 2] cycloaddition of two enones and an alkyne.
Ogoshi, Sensuke; Nishimura, Akira; Ohashi, Masato; Organic letters 12 (2010) 3450–3452; doi:10.1021/ol101264r

data_1503086
_publ_section_title
;
 Nickel-catalyzed [2 + 2 + 2] cycloaddition of two enones and an alkyne.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3450
_journal_page_last               3452
_journal_paper_doi               10.1021/ol101264r
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C44 H49 Ni O P '
_chemical_formula_sum            'C44 H49 Ni O P'
_chemical_formula_weight         683.54
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.9023(15)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.8408(5)
_cell_length_b                   15.1873(6)
_cell_length_c                   18.4530(9)
_cell_measurement_reflns_used    21072
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.1
_cell_volume                     3564.5(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40655
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.88
_refine_diff_density_min         -0.85
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     425
_refine_ls_number_reflns         10301
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0457P)^2^+3.3224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                6995
_reflns_number_total             10301
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol101264r_si_002.cif
_cod_data_source_block           '_15'
_cod_original_formula_sum        'C44 H49 Ni O P '
_cod_database_code               1503086