Synthesis and Profiling of a Diverse Collection of Azetidine-Based Scaffolds for the Development of CNS-Focused Lead-like Libraries
Jason T. Lowe; Maurice D. Lee; Lakshmi B. Akella; Emeline Davoine; Etienne J. Donckele; Landon Durak; Jeremy R. Duvall; Baudouin Gerard; Edward B. Holson; Adrien Joliton; Sarathy Kesavan; Berenice C. Lemercier; Haibo Liu; Jean-Charles Marié; Carol A. Mulrooney; Giovanni Muncipinto; Morgan Welzel-O'Shea; Laura M. Panko; Ann Rowley; Byung-Chul Suh; Meryl Thomas; Florence F. Wagner; Jingqiang Wei; Michael A. Foley; Lisa A. Marcaurelle; Journal of Organic Chemistry 77 (2012) 7187–7211; doi:10.1021/jo300974j

data_4027419
_publ_section_title
;
 Synthesis and Profiling of a Diverse Collection of Azetidine-Based
 Scaffolds for the Development of CNS-Focused Lead-like Libraries
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7187
_journal_page_last               7211
_journal_paper_doi               10.1021/jo300974j
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H31 Br N2 O2'
_chemical_formula_weight         579.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0010(2)
_cell_length_b                   12.0602(2)
_cell_length_c                   23.3614(4)
_cell_measurement_reflns_used    9543
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.36
_cell_measurement_theta_min      3.78
_cell_volume                     2817.71(9)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.9.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            58074
_diffrn_reflns_theta_full        69.48
_diffrn_reflns_theta_max         69.48
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    2.247
_exptl_absorpt_correction_T_max  0.6621
_exptl_absorpt_correction_T_min  0.5521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0215
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.6405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0574
_reflns_number_gt                5243
_reflns_number_total             5285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300974j_si_010.cif
_cod_data_source_block           d11012
_cod_database_code               4027419