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_4026258
_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 H10 Br2 O6'
_chemical_formula_sum            'C10 H10 Br2 O6'
_chemical_formula_weight         386.00
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_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                90.00
_cell_angle_beta                 115.273(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.458(6)
_cell_length_b                   6.3995(19)
_cell_length_c                   13.491(5)
_cell_measurement_reflns_used    1458
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.70
_cell_measurement_theta_min      2.74
_cell_volume                     1284.9(8)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4037
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.324
_exptl_absorpt_correction_T_max  0.7304
_exptl_absorpt_correction_T_min  0.5849
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0410P)^2^+8.9009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2133
_reflns_number_total             2748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200223a_si_005.cif
_cod_data_source_block           3aprd
_cod_original_cell_volume        1285.0(8)
_cod_database_code               4026258