A chiral pool approach to the synthesis of optically active tetrahalo norbornyl building blocks.
Khan, Faiz Ahmed; Sudheer, Ch; Organic letters 10 (2008) 3029–3032; doi:10.1021/ol800990m

data_1504737
_publ_section_title
;
 A chiral pool approach to the synthesis of optically active tetrahalo
 norbornyl building blocks.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3029
_journal_page_last               3032
_journal_paper_doi               10.1021/ol800990m
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C10 H9.60 Cl4 O4'
_chemical_formula_sum            'C10 H9.6 Cl4 O4'
_chemical_formula_weight         335.58
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 94.309(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            10
_cell_length_a                   29.003(3)
_cell_length_b                   8.7758(7)
_cell_length_c                   13.4454(11)
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.10
_cell_measurement_theta_min      2.43
_cell_volume                     3412.5(5)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0932
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11378
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0.5
_diffrn_standards_number         60
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_max  0.9259
_exptl_absorpt_correction_T_min  0.9182
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS 2.10 (Bruker 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.159
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         7886
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0682
_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^)+(0.0279P)^2^+40.2538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1762
_reflns_number_gt                6132
_reflns_number_total             7886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800990m-file003.cif
_cod_data_source_block           23
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      C121
_cod_original_formula_sum        'C10 H9.60 Cl4 O4'
_cod_database_code               1504737