Aerobic and Ligand-Free Manganese-Catalyzed Homocoupling of Arenes or Aryl Halides via in Situ Formation of Aryllithiums.
Liu, Yujia; Bergès, Julien; Zaid, Yassir; Chahdi, Fouad Ouazzani; Van Der Lee, Arie; Harakat, Dominique; Clot, Eric; Jaroschik, Florian; Taillefer, Marc; The Journal of organic chemistry 84 (2019) 4413–4420; doi:10.1021/acs.joc.8b02834

data_4034257
_publ_section_title
;
 Aerobic and Ligand-Free Manganese-Catalyzed Homocoupling of Arenes or
 Aryl Halides via in Situ Formation of Aryllithiums.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4413
_journal_page_last               4420
_journal_paper_doi               10.1021/acs.joc.8b02834
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C21 H18'
_chemical_formula_sum            'C21 H18'
_chemical_formula_weight         270.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 106.322(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7369(7)
_cell_length_b                   18.281(2)
_cell_length_c                   10.7850(11)
_cell_measurement_reflns_used    1135
_cell_measurement_temperature    175
_cell_measurement_theta_max      26.4600
_cell_measurement_theta_min      2.3080
_cell_volume                     1463.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      175
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.852
_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    -23.00  24.00   1.00  125.00    --  -16.62-100.00  30.00   47
  2  \w     43.00  80.00   1.00  125.00    --   17.25  57.00 -30.00   37
  3  \w    -50.00  88.00   1.00  125.00    --   17.25   0.00 150.00  138
;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0073356000
_diffrn_orient_matrix_UB_12      0.0282539000
_diffrn_orient_matrix_UB_13      -0.0461982000
_diffrn_orient_matrix_UB_21      0.0687378000
_diffrn_orient_matrix_UB_22      0.0199258000
_diffrn_orient_matrix_UB_23      0.0447314000
_diffrn_orient_matrix_UB_31      0.0659908000
_diffrn_orient_matrix_UB_32      -0.0175558000
_diffrn_orient_matrix_UB_33      -0.0237639000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6913
_diffrn_reflns_theta_full        26.491
_diffrn_reflns_theta_max         29.106
_diffrn_reflns_theta_min         2.228
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.81
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1969
_refine_ls_R_factor_gt           0.1258
_refine_ls_shift/su_max          0.0000637
_refine_ls_shift/su_mean         0.0000121
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982)
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 15.9 12.0 13.6 4.76 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1285
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1028
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1875
_reflns_number_total             3353
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.84
_oxford_diffrn_Wilson_scale      0.10
_oxford_refine_ls_r_factor_ref   0.1258
_oxford_refine_ls_scale          3.92(2)
_oxford_reflns_number_all        3353
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            jo8b02834_si_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        1463.94(15)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4034257
_cell_oxdiff_length_a            7.7350(6)
_cell_oxdiff_length_b            18.2926(18)
_cell_oxdiff_length_c            10.7829(10)
_cell_oxdiff_angle_alpha         90.055(8)
_cell_oxdiff_angle_beta          106.360(8)
_cell_oxdiff_angle_gamma         90.042(7)
_cell_oxdiff_volume              1463.9(2)
_oxdiff_exptl_absorpt_empirical_full_min 0.942
_oxdiff_exptl_absorpt_empirical_full_max 1.060
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_montpellier_reflns_maxres       0.80
_montpellier_reflns_completeness_maxres 99.87
_montpellier_reflns_redundancy_maxres 2.13