Ion-pairing catalysis in the enantioselective addition of hydrazones to N-acyldihydropyrrole derivatives.
Zabaleta, Nagore; Uria, Uxue; Reyes, Efraim; Carrillo, Luisa; Vicario, Jose L.; Chemical communications (Cambridge, England) 54 (2018) 8905–8908; doi:10.1039/c8cc05311a

data_7121981
_publ_section_title
;
 Ion-pairing catalysis in the enantioselective addition of hydrazones to
 N-acyldihydropyrrole derivatives.
;
_journal_issue                   64
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8905
_journal_page_last               8908
_journal_paper_doi               10.1039/c8cc05311a
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H20 F6 N4 O1 S1'
_chemical_formula_sum            'C22 H20 F6 N4 O S'
_chemical_formula_weight         502.48
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-02T11:43:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-05-04 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                92.8838(11)
_cell_angle_beta                 91.5768(11)
_cell_angle_gamma                94.1281(11)
_cell_formula_units_Z            6
_cell_length_a                   12.62193(18)
_cell_length_b                   13.55916(19)
_cell_length_c                   20.6596(3)
_cell_measurement_reflns_used    50753
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.025
_cell_measurement_theta_min      3.983
_cell_measurement_wavelength     1.54184
_cell_volume                     3520.38(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -1.00  24.00   1.00    1.00    --   38.00  91.00  63.00   25
  2  \w     -1.00  24.00   1.00    1.00    --   38.00  92.00-126.85   25
  3  \w   -110.00 -11.00   1.00    1.00    --  -41.08 -57.00 120.00   99
  4  \w    -71.00  30.00   1.00    1.00    --  -41.08  57.00 -90.00  101
  5  \w   -115.00 -18.00   1.00    1.00    --  -41.08 -38.00-150.00   97
  6  \w     16.00  61.00   1.00    1.00    --   41.08  38.00 -60.00   45
  7  \w     66.00 116.00   1.00    1.00    --   41.08  38.00 -60.00   50
  8  \w     15.00  72.00   1.00    1.00    --   41.08  57.00  30.00   57
  9  \w      3.00  98.00   1.00    1.00    --   41.08-125.00  90.00   95
 10  \w     12.00  37.00   1.00    1.00    --   46.00  80.00 165.96   25
 11  \w     10.00  35.00   1.00    1.00    --   46.00  84.00 -95.80   25
 12  \w     15.00  40.00   1.00    1.00    --   50.00  82.00 106.29   25
 13  \w     19.00  44.00   1.00    1.00    --   54.00  81.00  62.27   25
 14  \w     19.00  44.00   1.00    1.00    --   54.00  81.00-152.53   25
 15  \w     19.00  44.00   1.00    1.00    --   54.00  81.00 -50.91   25
 16  \w     20.00  45.00   1.00    1.00    --   54.00  80.00 166.67   25
 17  \w     19.00  44.00   1.00    1.00    --   54.00  82.00   9.33   25
 18  \w     92.00 122.00   1.00    1.00    --   58.00  75.00 -19.32   30
 19  \w     27.00  54.00   1.00    1.00    --   58.00  75.00 -19.32   27
 20  \w     32.00  59.00   1.00    1.00    --   66.00  77.00-142.83   27
 21  \w     33.00  60.00   1.00    1.00    --   66.00  76.00-103.17   27
 22  \w    -59.00 -33.00   1.00    6.00    --  -66.00 -76.00  90.24   26
 23  \w    108.00 135.00   1.00    1.00    --   66.00  77.00-142.83   27
 24  \w     36.00  62.00   1.00    1.00    --   70.00  77.00  76.65   26
 25  \w     37.00  64.00   1.00    1.00    --   70.00  75.00 -82.19   27
 26  \w    -69.00 -42.00   1.00    6.00    --  -74.00 -74.00 -31.10   27
 27  \w    -68.00 -41.00   1.00    6.00    --  -74.00 -75.00  -3.69   27
 28  \w    -67.00 -41.00   1.00    6.00    --  -74.00 -72.00 118.25   26
 29  \w    -68.00 -41.00   1.00    6.00    --  -74.00 -74.00 148.14   27
 30  \w    -67.00 -40.00   1.00    6.00    --  -74.00 -77.00 -72.85   27
 31  \w    -75.00 -41.00   1.00    6.00    --  -74.00 -74.00  23.99   34
 32  \w    -71.00 -45.00   1.00    6.00    --  -78.00 -75.00  63.77   26
 33  \w    -77.00 -50.00   1.00    6.00    --  -83.00 -73.00-169.06   27
 34  \w    -91.00 -50.00   1.00    6.00    --  -83.00 -74.00  18.76   41
 35  \w    -76.00 -50.00   1.00    6.00    --  -83.00 -74.00-144.53   26
 36  \w    -76.00 -50.00   1.00    6.00    --  -83.00 -73.00 146.16   26
 37  \w   -158.00 -81.00   1.00    6.00    --  -83.00 -73.00 146.16   77
 38  \w    -75.00 -49.00   1.00    6.00    --  -83.00 -77.00  90.00   26
 39  \w    -85.00 -49.00   1.00    6.00    --  -83.00 -77.00  47.75   36
 40  \w    -76.00 -50.00   1.00    6.00    --  -83.00 -76.00 -96.66   26
 41  \w    -77.00 -50.00   1.00    6.00    --  -83.00 -77.00-120.00   27
 42  \w    -75.00 -49.00   1.00    6.00    --  -83.00 -77.00 -60.00   26
 43  \w    -74.00 -49.00   1.00    6.00    --  -83.00 -77.00-180.00   25
 44  \w   -156.00 -82.00   1.00    6.00    --  -83.00 -77.00-180.00   74
 45  \w    -75.00 -49.00   1.00    6.00    --  -83.00 -77.00  60.00   26
 46  \w    -75.00 -50.00   1.00    6.00    --  -83.00 -74.00 115.55   25
 47  \w   -161.00 -50.00   1.00    6.00    --  -83.00 -77.00   0.00  111
 48  \w    -74.00 -49.00   1.00    6.00    --  -83.00 -77.00 -30.00   25
 49  \w     58.00  86.00   1.00    6.00    --   90.00  71.00-163.23   28
 50  \w     38.00  64.00   1.00    6.00    --  108.36 -45.00 120.00   26
 51  \w     43.00  75.00   1.00    6.00    --  108.36 -45.00 -90.00   32
 52  \w     28.00  92.00   1.00    6.00    --  108.36 -94.00  60.00   64
 53  \w     37.00  65.00   1.00    6.00    --  108.36 -45.00  30.00   28
 54  \w     75.00 152.00   1.00    6.00    --  108.36  77.00  30.00   77
 55  \w     24.00 100.00   1.00    6.00    --  108.36 -94.00-120.00   76
 56  \w    107.00 150.00   1.00    6.00    --  108.36  77.00-120.00   43
 57  \w     75.00 102.00   1.00    6.00    --  108.36  77.00-120.00   27
 58  \w     38.00  63.00   1.00    6.00    --  108.36 -45.00-150.00   25
 59  \w     75.00 157.00   1.00    6.00    --  108.36  77.00  90.00   82
 60  \w     76.00 145.00   1.00    6.00    --  108.36  77.00   0.00   69
 61  \w     75.00 150.00   1.00    6.00    --  108.36  77.00-180.00   75
 62  \w     75.00 148.00   1.00    6.00    --  108.36  77.00 -60.00   73
 63  \w    110.00 157.00   1.00    6.00    --  108.36  77.00 -30.00   47
 64  \w     75.00 102.00   1.00    6.00    --  108.36  77.00 -30.00   27
 65  \w     38.00 122.00   1.00    6.00    --  108.36-125.00  60.00   84
 66  \w     76.00 155.00   1.00    6.00    --  108.36  77.00 120.00   79
 67  \w     45.00 115.00   1.00    6.00    --  108.36-125.00-120.00   70
 68  \w    114.00 149.00   1.00    6.00    --  108.36  77.00  60.00   35
 69  \w     75.00 102.00   1.00    6.00    --  108.36  77.00  60.00   27
 70  \w     83.00 110.00   1.00    6.00    --  108.36  61.00  90.00   27
 71  \w     34.00  76.00   1.00    6.00    --  108.36 -45.00  90.00   42
 72  \w     75.00 145.00   1.00    6.00    --  108.36  77.00 -90.00   70
 73  \w     81.00 108.00   1.00    6.00    --  108.36  61.00   0.00   27
 74  \w     28.00  97.00   1.00    6.00    --  108.36 -94.00 -60.00   69
 75  \w     82.00 109.00   1.00    6.00    --  108.36  61.00 -90.00   27
 76  \w     75.00 148.00   1.00    6.00    --  108.36  77.00 150.00   73
 77  \w     75.00 150.00   1.00    6.00    --  108.36  77.00-150.00   75
 78  \w     29.00 101.00   1.00    6.00    --  108.36 -94.00 120.00   72
 79  \w    119.00 155.00   1.00    6.00    --  108.36 125.00 120.00   36
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1141869
_diffrn_orient_matrix_UB_12      0.0418842
_diffrn_orient_matrix_UB_13      -0.0116991
_diffrn_orient_matrix_UB_21      0.0423555
_diffrn_orient_matrix_UB_22      -0.0995416
_diffrn_orient_matrix_UB_23      0.0170743
_diffrn_orient_matrix_UB_31      -0.0125195
_diffrn_orient_matrix_UB_32      -0.0367313
_diffrn_orient_matrix_UB_33      -0.0717752
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            72604
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1548
_exptl_crystal_size_max          0.699
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (93%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=0.006(6), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   -0.013(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2075
_refine_ls_number_reflns         25823
_refine_ls_number_restraints     363
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1080P)^2^+1.0297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                24814
_reflns_number_total             25823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc05311a2.cif
_cod_data_source_block           a20160356_nz906re
_cod_depositor_comments
'Adding full bibliography for 7121981--7121982.cif.'
_cod_original_cell_volume        3520.38(8)
_cod_database_code               7121981