Nickel-Catalysed Direct C2-Arylation of N-Heterocyclic Carbene
Ghadwal, Rajendra S.; Ho, Nga Kim; Neumann, Beate; Stammler, Georg; Menezes da Silva, Vitor Hugo; Watanabe, Daniel; Braga, Ataualpa A. C.; Dalton Trans.  (2017) –; doi:10.1039/C7DT03099A

data_7044017
_publ_section_title
;
 Nickel-Catalysed Direct C2-Arylation of N-Heterocyclic Carbene
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT03099A
_journal_year                    2017
_chemical_formula_moiety         'Br, C35 H46 N3'
_chemical_formula_sum            'C35 H46 Br N3'
_chemical_formula_weight         588.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-19
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2017-06-28 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0975(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.07979(11)
_cell_length_b                   26.6494(4)
_cell_length_c                   13.52664(16)
_cell_measurement_reflns_used    59052
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.6750
_cell_measurement_theta_min      2.1480
_cell_volume                     3260.11(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9665
_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     -4.00  96.00   1.00   27.50    --   25.97  77.00-120.00  100
  2  \w    -43.00  47.00   1.00   27.50    --   25.97 -57.00 120.00   90
  3  \w    -44.00  56.00   1.00   27.50    --   25.97 -77.00  30.00  100
  4  \w      6.00  95.00   1.00   27.50    --   25.97  57.00  90.00   89
  5  \w      6.00  95.00   1.00   27.50    --   25.97  57.00   0.00   89
  6  \w    -20.00  68.00   1.00   27.50    --   25.97 -99.00  90.00   88
  7  \w     -4.00  96.00   1.00   27.50    --   25.97  77.00 150.00  100
  8  \w    -44.00  56.00   1.00   27.50    --   25.97 -77.00 -60.00  100
  9  \w     -4.00  96.00   1.00   27.50    --   25.97  77.00   0.00  100
 10  \w    -20.00  68.00   1.00   27.50    --   25.97 -99.00-120.00   88
 11  \w    -99.00 -35.00   1.00   27.50    --  -23.50-178.00 120.00   64
 12  \w     -4.00  96.00   1.00   27.50    --   25.97  77.00  30.00  100
 13  \w    -17.00  70.00   1.00   27.50    --   25.97-103.00 -35.00   87
 14  \w    -47.00  99.00   1.00   27.50    --   25.97   0.00-150.00  146
 15  \w      6.00  95.00   1.00   27.50    --   25.97  57.00 -60.00   89
 16  \w     34.00 103.00   1.00   27.50    --   25.97-178.00-120.00   69
 17  \w    -20.00  68.00   1.00   27.50    --   25.97 -99.00  60.00   88
 18  \w    -47.00  99.00   1.00   27.50    --   25.97   0.00-180.00  146
 19  \w    -46.00  51.00   1.00   27.50    --   25.97 -38.00 -90.00   97
 20  \w      0.00  98.00   1.00   27.50    --   25.97  38.00 -60.00   98
 21  \w    -47.00  99.00   1.00   27.50    --   25.97   0.00 -90.00  146
 22  \w    -47.00  99.00   1.00   27.50    --   25.97   0.00 -60.00  146
 23  \w    -47.00  33.00   1.00   27.50    --   25.97   0.00 -30.00   80
 24  \w    -47.00  99.00   1.00   27.50    --   25.97   0.00-120.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196128000
_diffrn_orient_matrix_UB_12      -0.0246869000
_diffrn_orient_matrix_UB_13      -0.0134469000
_diffrn_orient_matrix_UB_21      -0.0758730000
_diffrn_orient_matrix_UB_22      -0.0066855000
_diffrn_orient_matrix_UB_23      -0.0062309000
_diffrn_orient_matrix_UB_31      -0.0031077000
_diffrn_orient_matrix_UB_32      0.0073805000
_diffrn_orient_matrix_UB_33      -0.0505079000
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            188113
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.080
_diffrn_reflns_theta_min         1.528
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.287
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         9564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0270P)^2^+2.1497P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8750
_reflns_number_total             9564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03099a2.cif
_cod_data_source_block           compound_3j
_cod_database_code               7044017
_chemical_oxdiff_formula         'C35 H46 N3 Br'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_date_sample_data_collection 2017-04-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.860
_shelx_res_checksum              51455
_shelxl_version_number           2013-2