Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-Endo-Dig Cyclization.
Fujino, Daishi; Yorimitsu, Hideki; Osuka, Atsuhiro; Organic letters 14 (2012) 2914–2917; doi:10.1021/ol301257m

data_1507753
_publ_section_title
;
 Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed
 Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic
 Halides via 5-Endo-Dig Cyclization.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2914
_journal_page_last               2917
_journal_paper_doi               10.1021/ol301257m
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C19 H25 N O4 '
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 105.2565(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2027(3)
_cell_length_b                   17.3219(4)
_cell_length_c                   7.9128(2)
_cell_measurement_reflns_used    7486
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      68.225
_cell_measurement_theta_min      4.31
_cell_volume                     1745.85(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8902
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         4.31
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.9321
_exptl_absorpt_correction_T_min  0.5992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Higashi, T. (1995). 
 Program for Absorption Correction.
 Rigaku Corporation, Tokyo, Japan. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism '
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0591P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                2373
_reflns_number_total             2807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301257m_si_002.cif
_cod_data_source_block           100610fu
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1507753