Unexpected Formation of (E)-4-Alkene 1,3-Diketones from the Three-Component Reaction of Lithium Selenolates with 1-(1-Alkynyl)cyclopropyl Ketones and Aldehydes
Jianfeng Xu; Luling Wu; Xian Huang; Journal of Organic Chemistry 76 (2011) 5598–5605; doi:10.1021/jo2005439

data_4026450
_publ_section_title
;
 Unexpected Formation of (E)-4-Alkene 1,3-Diketones from the
 Three-Component Reaction of Lithium Selenolates with
 1-(1-Alkynyl)cyclopropyl Ketones and Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5598
_journal_page_last               5605
_journal_paper_doi               10.1021/jo2005439
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C39 H32.5 Br N4.5 O5 Se'
_chemical_formula_weight         803.07
_chemical_name_systematic
; 
 ? 
;
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_symmetry_space_group_name_Hall  '-P 2yn'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 112.814(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0626(17)
_cell_length_b                   9.8120(9)
_cell_length_c                   22.219(2)
_cell_measurement_reflns_used    2375
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.980
_cell_measurement_theta_min      4.603
_cell_volume                     3830.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0607
_diffrn_reflns_av_sigmaI/netI    0.1108
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
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_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    2.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68005
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1628
_exptl_crystal_size_max          0.361
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_refine_diff_density_max         0.903
_refine_diff_density_min         -0.537
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_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         7108
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_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1895
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2005439_si_001.cif
_cod_data_source_block           cd20144
_cod_original_cell_volume        3830.7(6)
_cod_original_formula_sum        'C39 H32.50 Br N4.50 O5 Se'
_cod_database_code               4026450