Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of Cycloalkanone-Derived Chalcones and Cloke-Wilson Rearrangement
Elumalai Gopi; Irishi N. N. Namboothiri; Journal of Organic Chemistry 78 (2013) 910–919; doi:10.1021/jo3022988

data_4027888
_publ_section_title
;
 Synthesis of Fused Bromofurans via Mg-Mediated Dibromocyclopropanation of
 Cycloalkanone-Derived Chalcones and Cloke-Wilson Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              910
_journal_page_last               919
_journal_paper_doi               10.1021/jo3022988
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H12 Br2 O'
_chemical_formula_sum            'C20 H12 Br2 O'
_chemical_formula_weight         428.12
_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                97.749(3)
_cell_angle_beta                 117.692(2)
_cell_angle_gamma                92.803(3)
_cell_formula_units_Z            4
_cell_length_a                   11.7848(4)
_cell_length_b                   12.5578(8)
_cell_length_c                   12.5773(4)
_cell_measurement_reflns_used    8087
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.45
_cell_measurement_theta_min      1.65
_cell_volume                     1619.82(13)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       '\w and \f 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  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27307
_diffrn_reflns_theta_full        28.45
_diffrn_reflns_theta_max         28.45
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    5.005
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0301P)^2^+0.1412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                5156
_reflns_number_total             8087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3022988_si_002.cif
_cod_data_source_block           fin
_cod_database_code               4027888