Grob Fragmentation of Norbornyl α-Diketones: A Route to α-Ketoenols and Aromatic Compounds
Faiz Ahmed Khan; Ch. Nageswara Rao; Journal of Organic Chemistry 76 (2011) 3320–3328; doi:10.1021/jo200223a

data_4026257
_publ_section_title
;
 Grob Fragmentation of Norbornyl \a-Diketones: A Route to \a-Ketoenols and
 Aromatic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3320
_journal_page_last               3328
_journal_paper_doi               10.1021/jo200223a
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C10 H9 B1 Br2 F2 O6'
_chemical_formula_sum            'C10 H9 B Br2 F2 O6'
_chemical_formula_weight         433.77
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.987(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   6.778(5)
_cell_length_b                   10.779(5)
_cell_length_c                   18.776(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1351.0(12)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8758
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.013
_exptl_absorpt_correction_T_max  1.1009
_exptl_absorpt_correction_T_min  0.9876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.036
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.255
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0475P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                2876
_reflns_number_total             3309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200223a_si_004.cif
_cod_data_source_block           17marem
_cod_original_formula_sum        'C10 H9 B1 Br2 F2 O6'
_cod_database_code               4026257