Stereocontrolled Synthesis and Pharmacological Evaluation of cis-2,6-Diphenethyl-1-azabicyclo[2.2.2]octanes as Lobelane Analogues
Guangrong Zheng; Linda P. Dwoskin; Agripina G. Deaciuc; Peter A. Crooks; Journal of Organic Chemistry 74 (2009) 6072–6076; doi:10.1021/jo901082r

data_4024770
_publ_section_title
;
Stereocontrolled Synthesis and Pharmacological Evaluation
of cis-2,6-Diphenethyl-1-azabicyclo[2.2.2]octanes as Lobelane Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6072
_journal_page_last               6076
_journal_paper_doi               10.1021/jo901082r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C16 H12 Cl3 N O3'
_chemical_formula_weight         372.62
_space_group_IT_number           2
_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           SHELXL-97
_cell_angle_alpha                63.082(1)
_cell_angle_beta                 74.631(1)
_cell_angle_gamma                82.194(1)
_cell_formula_units_Z            2
_cell_length_a                   9.6240(2)
_cell_length_b                   9.9066(2)
_cell_length_c                   10.2640(2)
_cell_measurement_reflns_used    3710
_cell_measurement_temperature    120.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     841.25(3)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1994)'
_computing_publication_material
; 
SHELX97-2 (Sheldrick, 1997) and local procedures 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\w scans at fixed \c = 55\%'
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7357
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.8733
_exptl_absorpt_correction_T_min  0.8507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.487
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.487
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0451P)^2^+0.4771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3087
_reflns_number_total             3861
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo901082r_si_001.cif
_cod_data_source_block           k03192
_cod_database_code               4024770