Synthesis of Alkylidenecyclopropanes by Palladium-Catalyzed Reaction of Propargyl-Substituted Malonate Esters with Aryl Halides by Anti-carbopalladation Pathway
Daishi Fujino; Hideki Yorimitsu; Koichiro Oshima; Journal of the American Chemical Society 133 (2011) 9682–9685; doi:10.1021/ja203062z

data_4106322
_publ_section_title
;
 Synthesis of Alkylidenecyclopropanes by Palladium-Catalyzed Reaction of
 Propargyl-Substituted Malonate Esters with Aryl Halides by
 Anti-carbopalladation Pathway
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9682
_journal_page_last               9685
_journal_paper_doi               10.1021/ja203062z
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C21 H17 F3 O4'
_chemical_formula_sum            'C21 H17 F3 O4'
_chemical_formula_weight         390.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 100.482(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.674(5)
_cell_length_b                   7.919(2)
_cell_length_c                   18.528(7)
_cell_measurement_reflns_used    14065
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      3.00
_cell_volume                     1828.5(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17081
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.9119
_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    1.418
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0572P)^2^+0.7387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                3513
_reflns_number_total             4185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja203062z_si_002.cif
_cod_data_source_block           00927fuj
_cod_original_cell_volume        1828.3(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4106322