Chemistry and Behavioral Studies Identify Chiral Cyclopropanes as Selective α4β2-Nicotinic Acetylcholine Receptor Partial Agonists Exhibiting an Antidepressant Profile.
Zhang, Hankun; Tückmantel, Werner; Eaton, J. Brek; Yuen, Po-Wai; Yu, Li-Fang; Bajjuri, Krishna Mohan; Fedolak, Allison; Wang, Daguang; Ghavami, Afshin; Caldarone, Barbara; Paterson, Neil E.; Lowe, David A.; Brunner, Daniela; Lukas, Ronald J.; Kozikowski, Alan P.; Journal of medicinal chemistry 55 (2012) 717–724; doi:10.1021/jm201157c

data_1503454
_publ_section_title
;
 Chemistry and Behavioral Studies Identify Chiral Cyclopropanes as
 Selective \a4\b2-Nicotinic Acetylcholine Receptor Partial Agonists
 Exhibiting an Antidepressant Profile.
;
_journal_issue                   2
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              717
_journal_page_last               724
_journal_paper_doi               10.1021/jm201157c
_journal_volume                  55
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'O4 N2 C25 H22'
_chemical_formula_sum            'C25 H22 N2 O4'
_chemical_formula_weight         414.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                89.990(6)
_cell_angle_beta                 90.002(6)
_cell_angle_gamma                89.995(6)
_cell_formula_units_Z            4
_cell_length_a                   6.2608(2)
_cell_length_b                   27.9762(20)
_cell_length_c                   11.5615(4)
_cell_measurement_reflns_used    10035
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.16
_cell_volume                     2025.04(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13223
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             872.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.320
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     560
_refine_ls_number_reflns         6250
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0554P)^2^+1.2463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1598
_reflns_number_gt                3996
_reflns_number_total             6250
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jm201157c_si_002.cif
_cod_data_source_block           '_psychogenics_wt01'
_cod_original_cell_volume        2025.05(18)
_cod_original_formula_sum        'O4 N2 C25 H22'
_cod_database_code               1503454