5(6)-anti-Substituted-2-azabicyclo[2.1.1]hexanes: A Nucleophilic Displacement Route
Grant R. Krow; Ram Edupuganti; Deepa Gandla; Amit Choudhary; Guoliang Lin; Philip E. Sonnet; Charles DeBrosse; Charles W. Ross; Kevin C. Cannon; Ronald T. Raines; Journal of Organic Chemistry 74 (2009) 8232–8242; doi:10.1021/jo901725k

data_4024958
_publ_contact_author_address
;
Department of Biochemistry
University of Wisconsin-Madison
433 Babcock Drive
Madison, WI  53706
USA
;
_publ_contact_author_email       rtraines@wisc.edu
_publ_contact_author_fax         608-262-3453
_publ_contact_author_name
;
Raines, Ronald T.
;
_publ_contact_author_phone       608-262-8588
_publ_section_title
;
5(6)-anti-Substituted-2-azabicyclo[2.1.1]hexanes: A Nucleophilic
Displacement Route
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8232
_journal_page_last               8242
_journal_paper_doi               10.1021/jo901725k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C12 H13 Br2 N'
_chemical_formula_sum            'C12 H13 Br2 N'
_chemical_formula_weight         331.05
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.10.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.586(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2022(9)
_cell_length_b                   10.8080(13)
_cell_length_c                   15.863(2)
_cell_measurement_reflns_used    8434
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9481
_cell_measurement_theta_min      2.6044
_cell_volume                     1217.5(3)
_computing_cell_refinement       'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_collection       'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXTL Ver. 6.10'
_computing_publication_material  'SHELXTL Ver. 6.10'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker CCD-1000 area detector'
_diffrn_measurement_method       '0.30\% \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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17977
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.625
_exptl_absorpt_correction_T_max  0.2882
_exptl_absorpt_correction_T_min  0.1673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2003) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.868
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+1.1170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                3075
_reflns_number_total             3485
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo901725k_si_005.cif
_cod_data_source_block           raines22
_cod_database_code               4024958