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_4027887
_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_sum            'C19 H16 Br2 O2'
_chemical_formula_weight         436.14
_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                63.4440(10)
_cell_angle_beta                 84.1330(10)
_cell_angle_gamma                71.8540(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0570(2)
_cell_length_b                   11.2036(2)
_cell_length_c                   12.3063(3)
_cell_measurement_reflns_used    5055
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.108
_cell_measurement_theta_min      3.366
_cell_volume                     826.26(4)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12706
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    4.912
_exptl_absorpt_correction_T_max  0.3835
_exptl_absorpt_correction_T_min  0.3041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.8742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                2095
_reflns_number_total             2829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3022988_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        826.26(3)
_cod_database_code               4027887