Synthesis of Conformationally Constrained 5-Fluoro- and 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics of Gauche- and Anti-3-Fluoro- and 3-Hydroxypyrrolidines
Grant R. Krow; Ram Edupuganti; Deepa Gandla; Fang Yu; Matthew Sender; Philip E. Sonnet; Michael J. Zdilla; Charles DeBrosse; Kevin C. Cannon; Charles W. Ross; Amit Choudhary; Matthew D. Shoulders; Ronald T. Raines; Journal of Organic Chemistry 76 (2011) 3626–3634; doi:10.1021/jo200117p

data_4026286
_publ_section_title
;
 Synthesis of Conformationally Constrained 5-Fluoro- and
 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics of Gauche- and
 Anti-3-Fluoro- and 3-Hydroxypyrrolidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3626
_journal_page_last               3634
_journal_paper_doi               10.1021/jo200117p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C5 H7 N (OH)1 (COCH3)1'
_chemical_formula_sum            'C7 H11 N O2'
_chemical_formula_weight         141.17
_chemical_name_common            5-syn-hydroxyMetpyr
_chemical_name_systematic
;
N-t-butoxycarbonyl-5-syn-hydroxy-2-azabicyclo[2.1.1]hexane
;
_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                90.006(2)
_cell_angle_beta                 90.002(2)
_cell_angle_gamma                90.000(2)
_cell_formula_units_Z            8
_cell_length_a                   6.7895(6)
_cell_length_b                   11.8108(10)
_cell_length_c                   17.2811(14)
_cell_measurement_reflns_used    13498
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.214
_cell_measurement_theta_min      2.982
_cell_volume                     1385.8(2)
_computing_cell_refinement       'SAINT (Bruker AXS)'
_computing_data_collection       'COSMO (Bruker AXS)'
_computing_data_reduction        'SADABS (Bruker AXS)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'APEX2 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Kappa Apex II DUO'
_diffrn_measurement_method       'psi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15974
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 15974 Corrected reflections written to file
 Estimated minimum and maximum transmission:  0.6575  0.7456
 The ratio of these values is more reliable than their absolute values!
 Additional spherical absorption correction applied with mu*r =  0.2000
 Lambda/2 correction factor = 0.0015
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       bar
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         15974
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0765P)^2^+0.4400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1612
_reflns_number_gt                12244
_reflns_number_total             15974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200117p_si_004.cif
_cod_data_source_block           sg2twin
_cod_database_code               4026286