Asymmetric Synthesis of α-Trifluoromethyl Pyrrolidines through Organocatalyzed 1,3-Dipolar Cycloaddition Reaction.
Dong, Zhenghao; Zhu, Yuanyuan; Li, Boyu; Wang, Cui; Yan, Wenjin; Wang, Kairong; Wang, Rui; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.6b02949

data_4032669
_publ_section_title
;
 Asymmetric Synthesis of \a-Trifluoromethyl Pyrrolidines through
 Organocatalyzed 1,3-Dipolar Cycloaddition Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.6b02949
_journal_year                    2017
_chemical_formula_moiety         'C22 H25 Br F3 N O6'
_chemical_formula_sum            'C22 H25 Br F3 N O6'
_chemical_formula_weight         536.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-07-19
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5559(4)
_cell_length_b                   10.8496(5)
_cell_length_c                   21.9254(8)
_cell_measurement_reflns_used    1912
_cell_measurement_temperature    295.8(4)
_cell_measurement_theta_max      20.9540
_cell_measurement_theta_min      3.7110
_cell_volume                     2511.06(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295.8(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.8481
_diffrn_measurement_details
;
  1 omega  -31.00   89.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   19.0000  -90.0000 100

  2 omega   39.00   85.80   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075 -178.0000 -180.0000 39
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0630621000
_diffrn_orient_matrix_UB_12      -0.0064471000
_diffrn_orient_matrix_UB_13      0.0106625000
_diffrn_orient_matrix_UB_21      -0.0225414000
_diffrn_orient_matrix_UB_22      -0.0318152000
_diffrn_orient_matrix_UB_23      0.0260824000
_diffrn_orient_matrix_UB_31      0.0054655000
_diffrn_orient_matrix_UB_32      -0.0567550000
_diffrn_orient_matrix_UB_33      -0.0158459000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7148
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1096
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.2460P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                3238
_reflns_number_total             4764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02949_si_002.cif
_cod_data_source_block           sunqt0719
_cod_original_cell_volume        2511.04(17)
_cod_database_code               4032669
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C)
;
_shelx_hkl_checksum              7655
_shelx_res_checksum              93012
_shelxl_version_number           2013-2