A New Phenoxide Chelated IrIII N-Heterocyclic Carbene Complex and Its Application in Reductive Amination Reactions
Gülcemal, Derya; Gülcemal, Süleyman; Robertson, Craig M.; Xiao, Jianliang; Organometallics 34 (2015) 4394–; doi:10.1021/acs.organomet.5b00625

data_4087820
_publ_section_title
;
 A New Phenoxide Chelated IrIII N-Heterocyclic Carbene Complex and Its
 Application in Reductive Amination Reactions
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4394
_journal_paper_doi               10.1021/acs.organomet.5b00625
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C41 H52 Cl Ir N2 O, 0.5(C6 H14)'
_chemical_formula_sum            'C44 H59 Cl Ir N2 O'
_chemical_formula_weight         859.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0981(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.4042(2)
_cell_length_b                   14.33389(19)
_cell_length_c                   30.2111(5)
_cell_measurement_reflns_used    49440
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4880
_cell_measurement_theta_min      1.8610
_cell_volume                     7890.33(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega -110.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -68.0000    0.0000 125

  2 omega -110.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -68.0000  120.0000 125

  3 omega -110.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -68.0000  240.0000 125

  4 omega -110.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.0000  -30.0000   90.0000 125

  5 omega  -90.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000    0.0000    0.0000 180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0194599000
_diffrn_orient_matrix_UB_12      -0.0233988000
_diffrn_orient_matrix_UB_13      -0.0153773000
_diffrn_orient_matrix_UB_21      -0.0273574000
_diffrn_orient_matrix_UB_22      0.0133006000
_diffrn_orient_matrix_UB_23      -0.0178141000
_diffrn_orient_matrix_UB_31      0.0196920000
_diffrn_orient_matrix_UB_32      0.0415257000
_diffrn_orient_matrix_UB_33      -0.0029540000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            111053
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         1.808
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description
;
;
_exptl_crystal_F_000             3512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.045
_refine_diff_density_max         1.380
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     911
_refine_ls_number_reflns         16068
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0145P)^2^+24.5162P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12618
_reflns_number_total             16068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00625_si_002.cif
_cod_data_source_block           c2
_cod_original_cell_volume        7890.3(2)
_cod_database_code               4087820
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C24, C23, C22
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.02
Uanis(C35) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.2
Uanis(C31A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.2
Uanis(C24) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.2
4.a Ternary CH refined with riding coordinates:
 C25A(H25A), C29(H29), C28A(H28A), C22A(H22A), C23(H23), C26(H26)
4.b Secondary CH2 refined with riding coordinates:
 C14A(H14A,H14B), C15(H15A,H15B), C5S(H5SA,H5SB), C4S(H4SA,H4SB), C2S(H2SA,
 H2SB), C3S(H3SA,H3SB)
4.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C8(H8), C5(H5), C11(H11), C5A(H5A), C2(H2), C3(H3), C19A(H19A),
 C4(H4), C10A(H10A), C18(H18), C13A(H13A), C12A(H12A), C11A(H11A), C17A(H17A),
 C20(H20)
4.d Idealised Me refined as rotating group:
 C13(H13B,H13C,H13D), C38A(H38A,H38B,H38C), C36(H36D,H36E,H36F), C36A(H36A,
 H36B,H36C), C40(H40D,H40E,H40F), C37(H37D,H37E,H37F), C39A(H39A,H39B,H39C),
 C38(H38D,H38E,H38F), C14(H14C,H14D,H14E), C40A(H40A,H40B,H40C), C37A(H37A,H37B,
 H37C), C7A(H7AA,H7AB,H7AC), C6A(H6AA,H6AB,H6AC), C23A(H23A,H23B,H23C),
 C21A(H21A,H21B,H21C), C24A(H24A,H24B,H24C), C26A(H26A,H26B,H26C), C39(H39D,
 H39E,H39F), C28(H28B,H28C,H28D), C30(H30A,H30B,H30C), C29A(H29A,H29B,H29C),
 C6S(H6SA,H6SB,H6SC), C27A(H27A,H27B,H27C), C25(H25B,H25C,H25D), C27(H27D,H27E,
 H27F), C1S(H1SA,H1SB,H1SC), C22(H22B,H22C,H22D), C24(H24D,H24E,H24F)
;
_shelx_res_checksum              55725
_shelx_hkl_checksum              65915
_olex2_submission_special_instructions 'No special instructions were received'