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#$Date: 2016-03-25 15:14:08 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179915 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/10/7021082.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7021082
loop_
_publ_author_name
'Gülcemal, Süleyman'
'Gökçe, Aytaç Gürhan'
'Cetinkaya, Bekir'
_publ_section_title
;
 Iridium(i) N-heterocyclic carbene complexes of benzimidazol-2-ylidene:
 effect of electron donating groups on the catalytic transfer
 hydrogenation reaction.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7305
_journal_page_last               7311
_journal_paper_doi               10.1039/c2dt32482b
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C23 H34 Cl Ir N2'
_chemical_formula_sum            'C23 H34 Cl Ir N2'
_chemical_formula_weight         566.17
_chemical_name_common
;
(1,3-Diisopropyl-(5,6-dimethyl)benzimidazol-2-ylidene)
chloro(mu$4!-1,5-cyclooctadiene)iridium$I!
;
_chemical_name_systematic
;(1,3-Diisopropyl-(5,6-dimethyl)benzimidazol-2-ylidene)
chloro(μ⁴-1,5-cyclooctadiene)iridiumI
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      12
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 (Sheldrick, 2008)'
_cell_angle_alpha                90.00
_cell_angle_beta                 133.312(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.1618(16)
_cell_length_b                   14.1773(7)
_cell_length_c                   12.8587(11)
_cell_measurement_reflns_used    5439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3167
_cell_measurement_theta_min      3.2562
_cell_volume                     2276.5(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12104
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.193
_refine_diff_density_max         3.440
_refine_diff_density_min         -2.277
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+2.5671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                2567
_reflns_number_total             2843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt32482b.txt
_cod_data_source_block           glc39
_cod_original_cell_volume        2276.5(3)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7021082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C2 C 0.1971(3) -0.0492(3) 0.7469(5) 0.0302(10) Uani 1 1 d .
C3 C 0.1482(4) -0.0985(4) 0.7822(5) 0.0376(11) Uani 1 1 d .
H3 H 0.1473 -0.1641 0.7809 0.045 Uiso 1 1 calc R
C1 C 0.2893(5) 0.0000 0.6918(7) 0.0319(14) Uani 1 2 d S
C81 C 0.3209(5) -0.2389(4) 0.8067(7) 0.0525(14) Uani 1 1 d .
H81A H 0.3866 -0.2106 0.8899 0.079 Uiso 1 1 calc R
H81B H 0.3363 -0.2975 0.7864 0.079 Uiso 1 1 calc R
H81C H 0.2755 -0.2505 0.8239 0.079 Uiso 1 1 calc R
C21 C 0.4752(4) 0.0492(4) 0.6016(5) 0.0379(11) Uani 1 1 d .
H21 H 0.4327 0.0774 0.5066 0.045 Uiso 1 1 calc R
C4 C 0.1008(4) -0.0494(4) 0.8192(6) 0.0405(12) Uani 1 1 d .
C24 C 0.5144(4) -0.0503(4) 0.8494(5) 0.0470(14) Uani 1 1 d .
H24 H 0.4974 -0.0789 0.9013 0.056 Uiso 1 1 calc R
C8 C 0.2652(4) -0.1734(4) 0.6813(6) 0.0386(11) Uani 1 1 d .
H8 H 0.3114 -0.1690 0.6621 0.046 Uiso 1 1 calc R
C82 C 0.1597(5) -0.2091(5) 0.5471(7) 0.0613(17) Uani 1 1 d .
H82A H 0.1113 -0.2147 0.5605 0.092 Uiso 1 1 calc R
H82B H 0.1692 -0.2697 0.5239 0.092 Uiso 1 1 calc R
H82C H 0.1307 -0.1658 0.4706 0.092 Uiso 1 1 calc R
C22 C 0.5674(5) 0.1083(6) 0.7206(7) 0.0647(19) Uani 1 1 d .
H22A H 0.6311 0.0869 0.7429 0.078 Uiso 1 1 calc R
H22B H 0.5542 0.1729 0.6873 0.078 Uiso 1 1 calc R
C23 C 0.5889(7) 0.1074(7) 0.8514(7) 0.084(3) Uani 1 1 d .
H23A H 0.5873 0.1720 0.8748 0.101 Uiso 1 1 calc R
H23B H 0.6610 0.0839 0.9280 0.101 Uiso 1 1 calc R
C5 C 0.0531(5) -0.1028(5) 0.8649(7) 0.0549(16) Uani 1 1 d .
H5A H -0.0225 -0.0910 0.7986 0.082 Uiso 1 1 calc R
H5B H 0.0859 -0.0825 0.9586 0.082 Uiso 1 1 calc R
H5C H 0.0654 -0.1691 0.8668 0.082 Uiso 1 1 calc R
N1 N 0.2554(3) -0.0767(3) 0.7137(4) 0.0316(8) Uani 1 1 d .
Cl1 Cl 0.22679(16) 0.0000 0.4002(2) 0.0571(6) Uani 1 2 d S
Ir1 Ir 0.381178(17) 0.0000 0.64590(2) 0.02766(11) Uani 1 2 d S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C2 C3 133.3(5) . .
N1 C2 C2 106.4(3) . 6
C3 C2 C2 120.3(3) . 6
C4 C3 C2 119.4(5) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
N1 C1 N1 107.3(6) . 6
N1 C1 Ir1 126.3(3) . .
N1 C1 Ir1 126.3(3) 6 .
C8 C81 H81A 109.5 . .
C8 C81 H81B 109.5 . .
H81A C81 H81B 109.5 . .
C8 C81 H81C 109.5 . .
H81A C81 H81C 109.5 . .
H81B C81 H81C 109.5 . .
C21 C21 C22 124.2(4) 6 .
C21 C21 Ir1 71.18(15) 6 .
C22 C21 Ir1 111.6(4) . .
C21 C21 H21 114.1 6 .
C22 C21 H21 114.1 . .
Ir1 C21 H21 114.1 . .
C3 C4 C4 120.3(3) . 6
C3 C4 C5 119.4(6) . .
C4 C4 C5 120.3(4) 6 .
C24 C24 C23 122.7(5) 6 6
C24 C24 Ir1 70.06(17) 6 .
C23 C24 Ir1 113.2(4) 6 .
C24 C24 H24 114.4 6 .
C23 C24 H24 114.4 6 .
Ir1 C24 H24 114.4 . .
N1 C8 C82 111.0(5) . .
N1 C8 C81 112.5(4) . .
C82 C8 C81 114.0(5) . .
N1 C8 H8 106.3 . .
C82 C8 H8 106.3 . .
C81 C8 H8 106.3 . .
C8 C82 H82A 109.5 . .
C8 C82 H82B 109.5 . .
H82A C82 H82B 109.5 . .
C8 C82 H82C 109.5 . .
H82A C82 H82C 109.5 . .
H82B C82 H82C 109.5 . .
C23 C22 C21 115.5(5) . .
C23 C22 H22A 108.4 . .
C21 C22 H22A 108.4 . .
C23 C22 H22B 108.4 . .
C21 C22 H22B 108.4 . .
H22A C22 H22B 107.5 . .
C22 C23 C24 116.6(5) . 6
C22 C23 H23A 108.1 . .
C24 C23 H23A 108.1 6 .
C22 C23 H23B 108.1 . .
C24 C23 H23B 108.1 6 .
H23A C23 H23B 107.3 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C1 N1 C2 110.0(4) . .
C1 N1 C8 122.7(4) . .
C2 N1 C8 126.5(4) . .
C1 Ir1 C24 92.1(2) . 6
C1 Ir1 C24 92.1(2) . .
C24 Ir1 C24 39.9(3) 6 .
C1 Ir1 C21 161.18(15) . 6
C24 Ir1 C21 93.9(2) 6 6
C24 Ir1 C21 81.2(2) . 6
C1 Ir1 C21 161.18(15) . .
C24 Ir1 C21 81.2(2) 6 .
C24 Ir1 C21 93.9(2) . .
C21 Ir1 C21 37.6(3) 6 .
C1 Ir1 Cl1 90.37(19) . .
C24 Ir1 Cl1 159.90(17) 6 .
C24 Ir1 Cl1 159.90(17) . .
C21 Ir1 Cl1 90.15(15) 6 .
C21 Ir1 Cl1 90.15(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.386(6) .
C2 C3 1.387(7) .
C2 C2 1.394(10) 6
C3 C4 1.379(7) .
C3 H3 0.9300 .
C1 N1 1.351(6) .
C1 N1 1.351(6) 6
C1 Ir1 2.028(7) .
C81 C8 1.504(8) .
C81 H81A 0.9600 .
C81 H81B 0.9600 .
C81 H81C 0.9600 .
C21 C21 1.395(11) 6
C21 C22 1.492(8) .
C21 Ir1 2.162(5) .
C21 H21 0.9800 .
C4 C4 1.402(12) 6
C4 C5 1.500(8) .
C24 C24 1.427(12) 6
C24 C23 1.499(9) 6
C24 Ir1 2.092(5) .
C24 H24 0.9800 .
C8 N1 1.476(6) .
C8 C82 1.491(8) .
C8 H8 0.9800 .
C82 H82A 0.9600 .
C82 H82B 0.9600 .
C82 H82C 0.9600 .
C22 C23 1.454(9) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C24 1.499(9) 6
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
Cl1 Ir1 2.349(2) .
Ir1 C24 2.092(5) 6
Ir1 C21 2.162(5) 6
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C2 C3 C4 175.8(5) . .
C2 C2 C3 C4 -0.9(6) 6 .
C2 C3 C4 C4 0.9(6) . 6
C2 C3 C4 C5 -176.7(5) . .
C21 C21 C22 C23 -70.4(8) 6 .
Ir1 C21 C22 C23 11.0(9) . .
C21 C22 C23 C24 -1.9(13) . 6
N1 C1 N1 C2 1.3(7) 6 .
Ir1 C1 N1 C2 178.1(4) . .
N1 C1 N1 C8 171.8(3) 6 .
Ir1 C1 N1 C8 -11.4(8) . .
C3 C2 N1 C1 -177.9(5) . .
C2 C2 N1 C1 -0.8(4) 6 .
C3 C2 N1 C8 12.1(8) . .
C2 C2 N1 C8 -170.8(4) 6 .
C82 C8 N1 C1 -104.2(6) . .
C81 C8 N1 C1 126.8(6) . .
C82 C8 N1 C2 64.7(7) . .
C81 C8 N1 C2 -64.4(7) . .
N1 C1 Ir1 C24 -108.0(6) . 6
N1 C1 Ir1 C24 68.1(6) 6 6
N1 C1 Ir1 C24 -68.1(6) . .
N1 C1 Ir1 C24 108.0(6) 6 .
N1 C1 Ir1 C21 0.4(11) . 6
N1 C1 Ir1 C21 176.5(5) 6 6
N1 C1 Ir1 C21 -176.5(5) . .
N1 C1 Ir1 C21 -0.4(11) 6 .
N1 C1 Ir1 Cl1 91.9(5) . .
N1 C1 Ir1 Cl1 -91.9(5) 6 .
C24 C24 Ir1 C1 -90.76(9) 6 .
C23 C24 Ir1 C1 151.2(6) 6 .
C23 C24 Ir1 C24 -118.0(6) 6 6
C24 C24 Ir1 C21 106.92(16) 6 6
C23 C24 Ir1 C21 -11.1(6) 6 6
C24 C24 Ir1 C21 71.37(16) 6 .
C23 C24 Ir1 C21 -46.7(6) 6 .
C24 C24 Ir1 Cl1 172.4(5) 6 .
C23 C24 Ir1 Cl1 54.4(9) 6 .
C21 C21 Ir1 C1 178.4(7) 6 .
C22 C21 Ir1 C1 58.2(9) . .
C21 C21 Ir1 C24 108.18(18) 6 6
C22 C21 Ir1 C24 -12.0(5) . 6
C21 C21 Ir1 C24 70.23(18) 6 .
C22 C21 Ir1 C24 -50.0(5) . .
C22 C21 Ir1 C21 -120.2(5) . 6
C21 C21 Ir1 Cl1 -90.05(5) 6 .
C22 C21 Ir1 Cl1 149.7(5) . .
