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_1503087
_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         'C24 H26 O2'
_chemical_formula_sum            'C24 H26 O2'
_chemical_formula_weight         346.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.070(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2808(3)
_cell_length_b                   15.2707(5)
_cell_length_c                   12.1045(4)
_cell_measurement_reflns_used    11796
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.72
_cell_measurement_theta_min      3.67
_cell_volume                     1892.91(10)
_computing_cell_refinement       'Rigaku/RAPID Diffractometer Control'
_computing_data_collection       'Rigaku/RAPID Diffractometer Control'
_computing_data_reduction        'teXsan: PROCESS (MSC)'
_computing_molecular_graphics    'Ortep-3 (Louis J. Farrugia, 1999)'
_computing_publication_material  'SHELXL-97 and modified'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1999)'
_computing_structure_solution    'PATTY (Bueskens, et al., 1994)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_detector       'imaging plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16101
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_correction_T_min  0.7655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1999). Abscor - Empirical Absorption Correction based on
Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.4295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                2342
_reflns_number_total             3296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101264r_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-p 2yab'
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               1503087