Ring Enlargement versus Selenoetherification on the Reaction of Allenyl Oxindoles with Selenenylating Reagents
Benito Alcaide; Pedro Almendros; Amparo Luna; Gonzalo Gómez-Campillos; M. Rosario Torres; Journal of Organic Chemistry 77 (2012) 3549–3556; doi:10.1021/jo202495z

data_4027097
_publ_section_title
;
 Ring Enlargement versus Selenoetherification on the Reaction of Allenyl
 Oxindoles with Selenenylating Reagents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3549
_journal_page_last               3556
_journal_paper_doi               10.1021/jo202495z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C24 H20 Br N O2 Se'
_chemical_formula_weight         513.28
_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                72.535(2)
_cell_angle_beta                 81.060(3)
_cell_angle_gamma                76.979(3)
_cell_formula_units_Z            4
_cell_length_a                   9.2292(13)
_cell_length_b                   13.5016(19)
_cell_length_c                   18.493(3)
_cell_measurement_reflns_used    1238
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.60
_cell_measurement_theta_min      2.49
_cell_volume                     2132.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.1410
_diffrn_reflns_av_sigmaI/netI    0.3628
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16293
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    3.655
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.2553
_refine_ls_R_factor_gt           0.0764
_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^)+(0.0370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1752
_reflns_number_gt                2290
_reflns_number_total             7290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202495z_si_002.cif
_cod_data_source_block           al799
_cod_database_code               4027097