Trisubstituted 2-Trifluoromethyl Pyrrolidines via Catalytic Asymmetric Michael Addition/Reductive Cyclization.
Corbett, Michael T.; Xu, Qihai; Johnson, Jeffrey S.; Organic letters 16 (2014) 2362–2365; doi:10.1021/ol500679w

data_1515021
_publ_section_title
;
 Trisubstituted 2-Trifluoromethyl Pyrrolidines via Catalytic Asymmetric
 Michael Addition/Reductive Cyclization.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2362
_journal_page_last               2365
_journal_paper_doi               10.1021/ol500679w
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Br F3 N O3'
_chemical_formula_sum            'C17 H15 Br F3 N O3'
_chemical_formula_weight         418.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5626(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0685(4)
_cell_length_b                   9.5467(4)
_cell_length_c                   10.5065(5)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      4.41
_cell_volume                     867.19(7)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26165
_diffrn_reflns_theta_full        70.09
_diffrn_reflns_theta_max         70.09
_diffrn_reflns_theta_min         4.41
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.671
_exptl_absorpt_correction_T_max  0.6766
_exptl_absorpt_correction_T_min  0.4089
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0604 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.6043.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0178
_refine_ls_R_factor_gt           0.0177
_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^)+(0.0319P)^2^+0.0645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0463
_reflns_number_gt                3183
_reflns_number_total             3201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500679w_si_001.cif
_cod_data_source_block           x1310009
_cod_depositor_comments          'Adding full bibliography for 1515021.cif.'
_cod_database_code               1515021
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;