Iridium Complexes of CCC-Pincer N-Heterocyclic Carbene Ligands: Synthesis and Catalytic C−H Functionalization
Chianese, Anthony R.; Mo, Allen; Lampland, Nicole L.; Swartz, Raymond L.; Bremer, Paul T.; Organometallics 29 (2010) 3019–; doi:10.1021/om100302g

data_4066127
_publ_section_title
;
 Iridium Complexes of CCC-Pincer N-Heterocyclic Carbene Ligands: Synthesis
 and Catalytic C&#x2212;H Functionalization
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3019
_journal_paper_doi               10.1021/om100302g
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C38 H32 Cl1 Ir1 N5'
_chemical_formula_sum            'C38 H32 Cl Ir N5'
_chemical_formula_weight         786.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-02-28
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                77.637(3)
_cell_angle_beta                 78.668(2)
_cell_angle_gamma                76.019(3)
_cell_formula_units_Z            4.00000
_cell_length_a                   14.1102(4)
_cell_length_b                   14.3525(5)
_cell_length_c                   21.3146(7)
_cell_measurement_reflns_used    29450
_cell_measurement_temperature    110
_cell_measurement_theta_max      67.3131
_cell_measurement_theta_min      4.0771
_cell_volume                     4043.6(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.3533
_diffrn_detector_type            'Oxford Diffraction Ruby CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega  -10.00   32.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.2583 -116.0000    4.0000 28

  2 omega   -7.00   47.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583   37.0000   60.0000 36

  3 omega  -74.00  -17.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583    0.0000  120.0000 38

  4 omega   31.00   62.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583 -128.0000  -56.0000 21

  5 omega   14.00   69.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583 -113.0000  165.0000 37

  6 omega   58.00   94.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583   37.0000   60.0000 24

  7 omega  -12.00  109.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583    0.0000  120.0000 81

  8 omega -169.00 -143.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -154.0000  168.0000 17

  9 omega  -72.00  -45.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000 -180.0000 18

 10 omega -155.00 -129.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -161.0000   79.0000 17

 11 omega -157.00 -130.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -169.0000  -53.0000 18

 12 omega -159.00 -132.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -159.0000  -98.0000 18

 13 omega -171.00 -144.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -151.0000  133.0000 18

 14 omega -152.00 -125.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -165.0000    3.0000 18

 15 omega -158.00 -131.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -169.0000 -112.0000 18

 16 omega -169.00 -142.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -154.0000   35.0000 18

 17 omega -166.00 -139.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000 -158.0000  -21.0000 18

 18 omega   19.00   46.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500 -110.0000    2.0000 18

 19 omega   11.00   84.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -15.0000  -60.0000 49

 20 omega   46.00   91.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000  107.0000 30

 21 omega   73.00  124.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000 -176.0000 34

 22 omega   19.00   49.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -45.0000  -30.0000 20

 23 omega   15.00   69.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000 -176.0000 36

 24 omega  105.00  153.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   15.0000 -120.0000 32

 25 omega   25.00   94.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   15.0000 -120.0000 46

 26 omega   25.00   73.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -45.0000 -180.0000 32

 27 omega   58.00  130.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000  -25.0000 48

 28 omega   65.00  123.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   45.0000  -30.0000 39

 29 omega  104.00  176.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -15.0000  -60.0000 48

 30 omega   25.50   90.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500 -113.0000  -14.0000 43

 31 omega   27.00   61.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -66.0000   16.0000 23

 32 omega   20.00   54.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000  -25.0000 23

 33 omega   74.00  131.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000   55.0000 38

 34 omega   31.00   64.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -45.0000  120.0000 22

 35 omega   24.00   63.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -45.0000   90.0000 26

 36 omega   16.00   49.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000   55.0000 22

 37 omega   24.00   73.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   15.0000    0.0000 33

 38 omega  140.00  173.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   15.0000    0.0000 22

 39 omega   77.00  104.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -73.0000  139.0000 18

 40 omega   23.00   69.50   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -45.0000 -150.0000 31

 41 omega   19.00   73.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500  -45.0000   60.0000 36

 42 omega   58.50   90.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500 -110.0000    2.0000 21

 43 omega  -61.00   50.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583  -37.0000 -180.0000 74

 44 omega  -13.00   98.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583   37.0000 -180.0000 74

 45 phi    240.00  360.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
  40.0000   18.2583    0.0000     -     80

 46 omega   -1.00   77.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583 -128.0000  -56.0000 52

 47 omega  -61.00   50.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583  -37.0000  -60.0000 74

 48 omega  -13.00   98.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583   37.0000  -60.0000 74

 49 omega  -13.00   68.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       18.2583 -113.0000  103.0000 54

 50 omega -169.00  -55.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -63.0000   78.0000 76

 51 omega -169.00  -55.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -63.0000 -113.0000 76

 52 omega -169.00  -55.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -65.0000   11.0000 76

 53 omega -169.00  -55.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -65.0000  137.0000 76

 54 omega -169.00  -55.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -65.0000  177.0000 76

 55 omega   65.00  173.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   45.0000 -120.0000 72

 56 omega   65.00  173.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   45.0000   30.0000 72

 57 omega   65.00  173.00   1.5000   29.0000
omega____ theta____ kappa____ phi______ frames
    -       96.2500   45.0000   90.0000 72

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w and \p scans'
_diffrn_orient_matrix_UB_11      0.0312986136
_diffrn_orient_matrix_UB_12      -0.0439308179
_diffrn_orient_matrix_UB_13      -0.0626619246
_diffrn_orient_matrix_UB_21      -0.0199593938
_diffrn_orient_matrix_UB_22      -0.0988472947
_diffrn_orient_matrix_UB_23      0.0387111530
_diffrn_orient_matrix_UB_31      -0.1076987315
_diffrn_orient_matrix_UB_32      0.0302640319
_diffrn_orient_matrix_UB_33      -0.0132164532
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            72312
_diffrn_reflns_theta_full        65.429
_diffrn_reflns_theta_max         67.3131
_diffrn_reflns_theta_min         4.0771
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_source_current           40
_diffrn_source_voltage           50
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    7.269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1556
_exptl_crystal_size_max          0.1562
_exptl_crystal_size_mid          0.0822
_exptl_crystal_size_min          0.0479
_platon_squeeze_details
;
;
_refine_diff_density_max         1.15
_refine_diff_density_min         -0.58
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9488
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     957
_refine_ls_number_reflns         14336
_refine_ls_number_restraints     276
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.009521
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.14P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0798
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0798
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                10932
_reflns_number_total             14336
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.90
_oxford_diffrn_Wilson_scale      0.66
_oxford_refine_ls_r_factor_ref   0.0386
_oxford_refine_ls_scale          1.362(3)
_oxford_reflns_number_all        14336
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            om100302g_si_002.cif
_cod_data_source_block           arc53
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_diffrn_radiation_probe' value 'X-ray' changed to
'x-ray' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C38 H32 Cl1 Ir1 N5'
_cod_database_code               4066127