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_4135355
_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         'C14 H28 Cl2 Fe N2'
_chemical_formula_sum            'C14 H28 Cl2 Fe N2'
_chemical_formula_weight         351.13
_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                   7.19727(16)
_cell_length_b                   10.5288(2)
_cell_length_c                   24.3626(6)
_cell_measurement_reflns_used    15192
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      28.3210
_cell_measurement_theta_min      2.9040
_cell_volume                     1846.16(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury 4.0.0 (CCDC, 2018)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_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    -13.00  88.00   1.00   10.00    --   11.66  77.00 120.00  101
  2  \w     35.00  69.00   1.00   10.00    --   11.66 178.00  30.00   34
  3  \w    -14.00  85.00   1.00   10.00    --   11.66  77.00 -90.00   99
  4  \w    -61.00  40.00   1.00   10.00    --   11.66 -57.00   0.00  101
  5  \w    -20.00  53.00   1.00   10.00    --   11.66 -99.00-120.00   73
  6  \w    -13.00  83.00   1.00   10.00    --   11.66  38.00  60.00   96
  7  \w    -20.00  53.00   1.00   10.00    --   11.66 -99.00 120.00   73
  8  \w    -84.00 -43.00   1.00   10.00    --  -11.97 149.00-136.51   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            30821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.677
_diffrn_reflns_theta_min         2.557
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense violet'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       irregular
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.205
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1573 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0352P)^2^+0.6597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0821
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                4317
_reflns_number_total             4830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09486_si_005.cif
_cod_data_source_block           ago-1-293
_cod_depositor_comments
'Adding full bibliography for 4135355--4135358.cif.'
_cod_original_cell_volume        1846.17(7)
_cod_database_code               4135355
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.646
_shelx_estimated_absorpt_t_max   0.806
_shelx_res_checksum              43418
_shelx_hkl_checksum              32230