Effect of bridgehead substitution in the Grob fragmentation of norbornyl ketones: a new route to substituted halophenols.
Choudhury, Sumit; Ahmad, Saeed; Khan, Faiz Ahmed; Organic & biomolecular chemistry 13 (2015) 9686–9696; doi:10.1039/c5ob01287b

data_7154627
_publ_section_title
;
 Effect of bridgehead substitution in the Grob fragmentation of norbornyl
 ketones: a new route to substituted halophenols.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9686
_journal_page_last               9696
_journal_paper_doi               10.1039/c5ob01287b
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C14 H10 Br2 O3'
_chemical_formula_sum            'C14 H10 Br2 O3'
_chemical_formula_weight         386.04
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_space_group_name_H-M   'P n 21 a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-02 deposited with the CCDC.
2015-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   7.871(5)
_cell_length_b                   11.094(5)
_cell_length_c                   15.506(5)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      2.26
_cell_volume                     1354.0(11)
_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    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'Diamond 2.1e'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_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  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8212
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    5.987
_exptl_absorpt_correction_T_max  0.4476
_exptl_absorpt_correction_T_min  0.3806
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.170
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0866P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1563
_reflns_number_gt                1865
_reflns_number_total             2782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01287b2.cif
_cod_data_source_block           10febbm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154627.cif.
;
_cod_database_code               7154627