Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes Provides Chiral Cyclooctadienes.
Braconi, Elena; Götzinger, Alissa C; Cramer, Nicolai; Journal of the American Chemical Society 142 (2020) 19819–19824; doi:10.1021/jacs.0c09486

data_4135357
_publ_section_title
;
 Enantioselective Iron-Catalyzed Cross-[4+4]-Cycloaddition of 1,3-Dienes
 Provides Chiral Cyclooctadienes.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              19819
_journal_page_last               19824
_journal_paper_doi               10.1021/jacs.0c09486
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H36 Cl2 Fe N2'
_chemical_formula_sum            'C18 H36 Cl2 Fe N2'
_chemical_formula_weight         407.24
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.33605(14)
_cell_length_b                   11.0844(2)
_cell_length_c                   26.8365(5)
_cell_measurement_reflns_used    9408
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.5660
_cell_measurement_theta_min      4.2860
_cell_volume                     2182.23(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.62a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Mercury 4.2.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_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    -82.00  -2.00   1.00    2.11    --  -42.74 125.00 150.00   80
  2  \w   -116.00 -20.00   1.00    2.11    --  -42.74 -37.00-120.00   96
  3  \w    -84.00  -2.00   1.00    2.11    --  -42.74 125.00 -30.00   82
  4  \w     12.00  64.00   1.00    2.11    --   42.74 -37.00  60.00   52
  5  \w     86.00 113.00   1.00    2.11    --   42.74  37.00 -60.00   27
  6  \w     39.00 129.00   1.00    8.41    --  103.26 -77.00  90.00   90
  7  \w     23.00  88.00   1.00    8.41    --  103.26 -94.00   0.00   65
  8  \w     33.00 117.00   1.00    8.41    --  103.26 -45.00 -30.00   84
  9  \w     80.00 133.00   1.00    8.41    --  103.26  45.00 -30.00   53
 10  \w     81.00 154.00   1.00    8.41    --  103.26  45.00   0.00   73
 11  \w     84.00 152.00   1.00    8.41    --  103.26  61.00 120.00   68
 12  \w     89.00 158.00   1.00    8.41    --  103.26  45.00-150.00   69
 13  \w     80.00 128.00   1.00    8.41    --  103.26  45.00 -60.00   48
 14  \w     81.00 108.00   1.00    8.41    --  103.26  45.00-120.00   27
 15  \w    120.00 166.00   1.00    8.41    --  103.26  45.00-120.00   46
 16  \w     28.00 122.00   1.00    8.41    --  103.26 -30.00  60.00   94
 17  \w     32.00 117.00   1.00    8.41    --  103.26-125.00 -60.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16376
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.675
_diffrn_reflns_theta_min         4.316
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.784
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.109
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.62a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark purple'
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0101(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0231
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.3077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0612
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4209
_reflns_number_total             4281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09486_si_003.cif
_cod_data_source_block           ago-01-807
_cod_depositor_comments
'Adding full bibliography for 4135355--4135358.cif.'
_cod_database_code               4135357
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.148
_shelx_estimated_absorpt_t_max   0.445
_shelx_res_checksum              55997
_shelx_hkl_checksum              71643