Palladium-catalyzed decarboxylative [4 + 3] cyclization of gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes.
Shintani, Ryo; Murakami, Masataka; Tsuji, Takaoki; Tanno, Hideyuki; Hayashi, Tamio; Organic letters 11 (2009) 5642–5645; doi:10.1021/ol902326s

data_1504292
_publ_section_title
;
 Palladium-catalyzed decarboxylative [4 + 3] cyclization of
 gamma-methylidene-delta-valerolactones with 1,1-dicyanocyclopropanes.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5642
_journal_page_last               5645
_journal_paper_doi               10.1021/ol902326s
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C22 H25 N O4 S'
_chemical_formula_weight         399.49
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_symmetry_space_group_name_H-M   'P 21 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   36.790(6)
_cell_length_b                   10.2861(14)
_cell_length_c                   10.833(2)
_cell_measurement_temperature    123(2)
_cell_volume                     4099.5(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            34220
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9295
_exptl_absorpt_correction_T_min  0.8812
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         8653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0257P)^2^+2.7582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                7731
_reflns_number_total             8653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902326s_si_003.cif
_cod_data_source_block           90829yuk
_cod_original_cell_volume        4099.4(12)
_cod_original_sg_symbol_H-M      ' P 21 21 2'
_cod_database_code               1504292