Palladacycle-Catalyzed Methylenecyclopropanation of Bicyclic Alkenes with Propiolates
Dong-Liang Mo; Teng Yuan; Chang-Hua Ding; Li-Xin Dai; Xue-Long Hou; Journal of Organic Chemistry 78 (2013) 11470–11476; doi:10.1021/jo402024v

data_4028763
_publ_section_title
;
 Palladacycle-Catalyzed Methylenecyclopropanation of Bicyclic Alkenes with
 Propiolates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11470
_journal_page_last               11476
_journal_paper_doi               10.1021/jo402024v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.390(14)
_cell_angle_beta                 70.626(13)
_cell_angle_gamma                86.718(14)
_cell_formula_units_Z            2
_cell_length_a                   7.471(6)
_cell_length_b                   9.498(7)
_cell_length_c                   9.667(7)
_cell_measurement_reflns_used    1230
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.255
_cell_measurement_theta_min      4.570
_cell_volume                     631.4(8)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3595
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7523
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0612
_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^)+(0.0853P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1599
_reflns_number_gt                1834
_reflns_number_total             2556
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402024v_si_003.cif
_cod_data_source_block           cd2836
_cod_database_code               4028763