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_7121982
_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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H18 F6 N4 O2'
_chemical_formula_sum            'C21 H18 F6 N4 O2'
_chemical_formula_weight         472.39
_chemical_name_systematic
;
 (S,Z)-N-argio-2-(1-formylpyrrolidin-2-yl)-2-(2-phenylhydrazono)acetamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-28T14:43:02-00:00
_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                90
_cell_angle_beta                 92.002(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.7773(15)
_cell_length_b                   5.4608(4)
_cell_length_c                   31.7244(19)
_cell_measurement_reflns_used    5279
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.322
_cell_measurement_theta_min      3.676
_cell_volume                     4116.7(5)
_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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.998
_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   -124.00 -99.00   1.00    4.00    --  -41.33 -99.00 -60.00   25
  2  \w   -108.00 -26.00   1.00    4.00    --  -41.33 -38.00   0.00   82
  3  \w    -71.00  33.00   1.00    4.00    --  -41.33  19.00   0.00  104
  4  \w   -128.00 -91.00   1.00   20.00    --  -83.00-125.00  90.00   37
  5  \w     50.00  77.00   1.00   20.00    --  108.36 -45.00-150.00   27
  6  \w     79.00 154.00   1.00   20.00    --  108.36  61.00 120.00   75
  7  \w     65.00 109.00   1.00   20.00    --  108.36 -94.00  60.00   44
  8  \w     70.00 141.00   1.00   20.00    --  108.36 -77.00 -60.00   71
  9  \w     30.00  69.00   1.00   20.00    --  108.36 -30.00  30.00   39
 10  \w     42.00  71.00   1.00   20.00    --  108.36 -38.00 -31.00   29
 11  \w     29.00  99.00   1.00   20.00    --  108.36 -94.00-120.00   70
 12  \w     45.00  75.00   1.00   20.00    --  108.36 -45.00-120.00   30
 13  \w     37.00  77.00   1.00   20.00    --  108.36 -45.00 -60.00   40
 14  \w     30.00  69.00   1.00   20.00    --  108.36 -30.00 120.00   39
 15  \w     43.00  98.00   1.00    4.00    --   41.33-125.00 -30.00   55
 16  \w     21.00  83.00   1.00    4.00    --   41.33-125.00 150.00   62
 17  \w   -149.00-100.00   1.00   20.00    --  -83.00 -77.00  30.00   49
 18  \w     33.00  80.00   1.00   20.00    --  108.36 -94.00 150.00   47
 19  \w     31.00  64.00   1.00   20.00    --  108.36 -30.00-150.00   33
 20  \w     35.00  64.00   1.00   20.00    --  108.36 -30.00 150.00   29
 21  \w     38.00  68.00   1.00   20.00    --  108.36 -45.00 -90.00   30
 22  \w     25.00  61.00   1.00   20.00    --  108.36 -15.00 -60.00   36
 23  \w     68.00 112.00   1.00   20.00    --  108.36 -15.00 -60.00   44
 24  \w    133.00 158.00   1.00   20.00    --  108.36 -15.00 -60.00   25
 25  \w     35.00  68.00   1.00   20.00    --  108.36 -45.00 120.00   33
 26  \w     69.00 115.00   1.00   20.00    --  108.36-125.00-120.00   46
 27  \w     75.00 102.00   1.00   20.00    --  108.36  77.00  90.00   27
 28  \w    112.00 141.00   1.00   20.00    --  108.36  77.00  90.00   29
 29  \w     68.00 122.00   1.00   20.00    --  108.36-125.00   0.00   54
 30  \w     30.00  68.00   1.00   20.00    --  108.36 -30.00-180.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0121283
_diffrn_orient_matrix_UB_12      0.0946508
_diffrn_orient_matrix_UB_13      0.0451588
_diffrn_orient_matrix_UB_21      -0.0607728
_diffrn_orient_matrix_UB_22      0.0965192
_diffrn_orient_matrix_UB_23      0.0015879
_diffrn_orient_matrix_UB_31      -0.0190595
_diffrn_orient_matrix_UB_32      -0.2474679
_diffrn_orient_matrix_UB_33      0.0179019
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15208
_diffrn_reflns_theta_full        69.97
_diffrn_reflns_theta_max         69.97
_diffrn_reflns_theta_min         3.72
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.202
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.744
_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            colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0867P)^2^+6.6025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                3074
_reflns_number_total             3904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc05311a2.cif
_cod_data_source_block           a20170014_nz1259
_cod_depositor_comments
'Adding full bibliography for 7121981--7121982.cif.'
_cod_database_code               7121982