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_4028762
_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 Br2 O3'
_chemical_formula_weight         402.08
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.223(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.033(2)
_cell_length_b                   10.0044(18)
_cell_length_c                   14.451(3)
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.917
_cell_measurement_theta_min      4.865
_cell_volume                     1588.5(5)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9146
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    5.107
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3665
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.391
_exptl_crystal_size_min          0.297
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0117(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                1752
_reflns_number_total             3443
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402024v_si_002.cif
_cod_data_source_block           cd28274
_cod_original_cell_volume        1588.4(5)
_cod_database_code               4028762