Palladium-catalyzed [2+1+1] annulation of norbornenes with (z)-bromostyrenes: synthesis of bismethylenecyclobutanes via twofold C(sp2)-H bond activation
Jiangang Mao; Weiliang Bao; Chem.Commun. 50 (2014) 15726–; doi:10.1039/C4cc06545J

data_7116089
_publ_section_title
;
 Palladium-catalyzed [2+1+1] annulation of norbornenes with
 (z)-bromostyrenes: synthesis of bismethylenecyclobutanes via twofold
 C(sp2)-H bond activation
;
_journal_name_full               Chem.Commun.
_journal_page_first              15726
_journal_paper_doi               10.1039/C4cc06545J
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C34 H31 N O2'
_chemical_formula_sum            'C34 H31 N O2'
_chemical_formula_weight         485.60
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   13.28280(18)
_cell_length_b                   10.65296(14)
_cell_length_c                   37.6191(5)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.4173
_cell_measurement_theta_min      3.3244
_cell_volume                     5323.15(12)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            22473
_diffrn_reflns_theta_full        67.53
_diffrn_reflns_theta_max         67.53
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.8639
_exptl_absorpt_correction_T_min  0.7643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00098(10)
_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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0650P)^2^+0.9482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                4152
_reflns_number_total             4759
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc06545j2.cif
_cod_data_source_block           121210_mjg0120202
_cod_database_code               7116089