Nickel(0)/N-Heterocyclic Carbene-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of Two Enones and an Alkyne: Access to Cyclohexenes with Four Contiguous Stereogenic Centers.
Kumar, Ravindra; Tokura, Hiromu; Nishimura, Akira; Mori, Tadashi; Hoshimoto, Yoichi; Ohashi, Masato; Ogoshi, Sensuke; Organic letters 17 (2015) 6018–6021; doi:10.1021/acs.orglett.5b02983

data_1540580
_publ_section_title
;
 Nickel(0)/N-Heterocyclic Carbene-Catalyzed Asymmetric [2 + 2 + 2]
 Cycloaddition of Two Enones and an Alkyne: Access to Cyclohexenes with
 Four Contiguous Stereogenic Centers.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6018
_journal_page_last               6021
_journal_paper_doi               10.1021/acs.orglett.5b02983
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H30 O2'
_chemical_formula_sum            'C34 H30 O2'
_chemical_formula_weight         470.58
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_symmetry_space_group_name_Hall  'P 65'
_symmetry_space_group_name_H-M   'P 65'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   26.2091(5)
_cell_length_b                   26.2091(5)
_cell_length_c                   6.7076(5)
_cell_measurement_reflns_used    10600
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      77.665
_cell_measurement_theta_min      3.375
_cell_volume                     3990.3(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    CrystalMaker
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013) and modified'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID 191R'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            77798
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.083
_diffrn_reflns_theta_min         3.373
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_platon_squeeze_details
;
TITL shelxl    P 65         R = 0.06
CELL   26.2091   26.2091    6.7076     90.00     90.00    120.00
SPGR P65
C101 0.991 0.992 0.841 !       1.41 eA-3
;
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4852
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.7275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4115
_reflns_number_total             4852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02983_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 1540580.cif.'
_cod_database_code               1540580
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.984
_shelx_fab_checksum              33414
_shelxl_version_number           2013-4
_shelx_res_checksum              40220
_shelx_hkl_checksum              35580