Serendipitously discovered diazomethane-mediated novel molecular rearrangements of norbornyl alpha-ketohemiketals.
Khan, Faiz Ahmed; Rao, G. Hari Mangeswara; Satapathy, Rashmirekha; Parasuraman, Karuppasamy; Organic letters 9 (2007) 1581–1584; doi:10.1021/ol070442g

data_1505377
_publ_section_title
;
 Serendipitously discovered diazomethane-mediated novel molecular
 rearrangements of norbornyl alpha-ketohemiketals.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1581
_journal_page_last               1584
_journal_paper_doi               10.1021/ol070442g
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C13 H18 Br2 O5'
_chemical_formula_sum            'C13 H18 Br2 O5'
_chemical_formula_weight         414.09
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5183(8)
_cell_length_b                   10.7917(10)
_cell_length_c                   16.3000(15)
_cell_measurement_temperature    100
_cell_volume                     1498.4(2)
_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_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  /w-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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0502
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9807
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.425
_exptl_absorpt_correction_T_max  0.5390
_exptl_absorpt_correction_T_min  0.4418
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.159
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.190
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.49(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0169P)^2^+12.5843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                3283
_reflns_number_total             3668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070442gsi20070221_084145.cif
_cod_data_source_block           17febdm
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_database_code               1505377