Synthesis of 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane, 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane, a Class of Potent Nicotinic Acetylcholine Receptor–Ligands
Balwinder S. Bhatti; Jon-Paul Strachan; Scott R. Breining; Craig H. Miller; Persida Tahiri; Peter A. Crooks; Niranjan Deo; Cynthia S. Day; William S. Caldwell; Journal of Organic Chemistry 73 (2008) 3497–3507; doi:10.1021/jo800028q

data_4023385
_publ_section_title
;
 Synthesis of 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane,
 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and
 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane,
 a Class of Potent Nicotinic Acetylcholine Receptor--Ligands
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3497
_journal_page_last               3507
_journal_paper_doi               10.1021/jo800028q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C26 H42 Cl4 N4 O'
_chemical_formula_weight         568.44
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-PC
_cell_angle_alpha                101.897(12)
_cell_angle_beta                 92.696(14)
_cell_angle_gamma                98.098(10)
_cell_formula_units_Z            1
_cell_length_a                   6.7509(9)
_cell_length_b                   9.4347(16)
_cell_length_c                   11.7308(16)
_cell_measurement_reflns_used    45
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12.53
_cell_measurement_theta_min      3.58
_cell_volume                     721.59(18)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker P4 1.0mm pinhole'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3796
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.54
_diffrn_standards_interval_count 397
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.7798
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.23(9)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.1041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2717
_reflns_number_total             3796
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800028q-File001_4.cif
_cod_data_source_block           targ3-1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4023385