#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:08:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178886 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/15/4111514.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_4111514
loop_
_publ_author_name
'Natalie M. Scott'
'Reto Dorta'
'Edwin D. Stevens'
'Andrea Correa'
'Luigi Cavallo'
'Steven P. Nolan'
_publ_section_title
;
 Interaction of a Bulky N-Heterocyclic Carbene Ligand with Rh(I) and
 Ir(I). Double C-H Activation and Isolation of Bare 14-Electron Rh(III)
 and Ir(III) Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3516
_journal_page_last               3526
_journal_paper_doi               10.1021/ja043249f
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C35 H50 Cl Ir N4 O'
_chemical_formula_weight         770.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.7340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9687(7)
_cell_length_b                   16.8897(8)
_cell_length_c                   15.5745(8)
_cell_measurement_reflns_used    23577
_cell_measurement_temperature    396(2)
_cell_measurement_theta_max      28.924
_cell_measurement_theta_min      2.412
_cell_volume                     3479.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      396(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21479
_diffrn_reflns_theta_full        20.00
_diffrn_reflns_theta_max         20.00
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    3.945
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.576214
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      0
_exptl_crystal_description       plate
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.981
_refine_diff_density_min         -1.612
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+25.7370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                3034
_reflns_number_total             3245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja043249fsi20041109_040253.cif
_cod_data_source_block           nol165m
_cod_database_code               4111514
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Ir1 Ir 0.32354(3) 0.390093(19) 0.76661(2) 0.01429(19) Uani 1 1 d U
Cl1 Cl 0.4486(2) 0.29770(15) 0.73415(17) 0.0348(7) Uani 1 1 d U
O1 O 0.1887(6) 0.3825(4) 0.5765(5) 0.0337(17) Uani 1 1 d U
N1 N 0.3377(5) 0.2907(4) 0.9229(5) 0.0150(16) Uani 1 1 d U
C1 C 0.2886(6) 0.2931(5) 0.8329(6) 0.015(2) Uiso 1 1 d U
N2 N 0.2248(5) 0.2287(4) 0.8166(5) 0.0160(16) Uani 1 1 d U
C2 C 0.3079(7) 0.2267(5) 0.9632(6) 0.020(2) Uiso 1 1 d U
H2 H 0.3323 0.2126 1.0241 0.024 Uiso 1 1 calc R
N3 N 0.3039(5) 0.5613(4) 0.7542(5) 0.0168(17) Uani 1 1 d U
C3 C 0.2375(7) 0.1893(6) 0.8978(6) 0.023(2) Uiso 1 1 d U
H3 H 0.2026 0.1443 0.9051 0.027 Uiso 1 1 calc R
N4 N 0.4358(5) 0.5431(4) 0.7121(4) 0.0154(16) Uani 1 1 d U
C4 C 0.4213(7) 0.3455(5) 0.9678(6) 0.018(2) Uiso 1 1 d U
C5 C 0.4264(8) 0.4093(6) 0.8994(6) 0.018(2) Uiso 1 1 d U
H5B H 0.404(5) 0.460(5) 0.919(5) 0.01(2) Uiso 1 1 d .
H5A H 0.493(6) 0.407(4) 0.896(5) 0.01(2) Uiso 1 1 d .
C6 C 0.5199(8) 0.2967(6) 0.9977(7) 0.035(3) Uiso 1 1 d U
H6A H 0.5157 0.2572 1.0407 0.053 Uiso 1 1 calc R
H6B H 0.5760 0.3312 1.0252 0.053 Uiso 1 1 calc R
H6C H 0.5292 0.2715 0.9457 0.053 Uiso 1 1 calc R
C7 C 0.4043(8) 0.3812(6) 1.0522(7) 0.035(3) Uiso 1 1 d U
H7A H 0.3398 0.4072 1.0352 0.052 Uiso 1 1 calc R
H7B H 0.4567 0.4189 1.0794 0.052 Uiso 1 1 calc R
H7C H 0.4057 0.3399 1.0949 0.052 Uiso 1 1 calc R
C8 C 0.1513(7) 0.2037(5) 0.7270(6) 0.023(2) Uiso 1 1 d U
C9 C 0.2094(7) 0.1907(6) 0.6597(6) 0.025(2) Uiso 1 1 d U
H9A H 0.2527 0.2353 0.6616 0.038 Uiso 1 1 calc R
H9B H 0.1623 0.1852 0.5996 0.038 Uiso 1 1 calc R
H9C H 0.2495 0.1435 0.6758 0.038 Uiso 1 1 calc R
C10 C 0.0685(7) 0.2664(6) 0.6964(6) 0.028(2) Uiso 1 1 d U
H10A H 0.0362 0.2725 0.7419 0.042 Uiso 1 1 calc R
H10B H 0.0194 0.2501 0.6404 0.042 Uiso 1 1 calc R
H10C H 0.0978 0.3159 0.6877 0.042 Uiso 1 1 calc R
C11 C 0.1035(8) 0.1253(6) 0.7375(7) 0.038(3) Uiso 1 1 d U
H11A H 0.1556 0.0868 0.7628 0.057 Uiso 1 1 calc R
H11B H 0.0610 0.1074 0.6792 0.057 Uiso 1 1 calc R
H11C H 0.0637 0.1319 0.7770 0.057 Uiso 1 1 calc R
C12 C 0.3636(6) 0.5029(5) 0.7380(5) 0.012(2) Uiso 1 1 d U
C13 C 0.3377(7) 0.6359(6) 0.7383(6) 0.023(2) Uiso 1 1 d U
H13 H 0.3086 0.6843 0.7443 0.027 Uiso 1 1 calc R
C14 C 0.4181(7) 0.6252(5) 0.7134(6) 0.020(2) Uiso 1 1 d U
H14 H 0.4567 0.6648 0.6991 0.024 Uiso 1 1 calc R
C15 C 0.2097(7) 0.5424(5) 0.7736(6) 0.020(2) Uiso 1 1 d U
C16 C 0.2194(7) 0.4571(5) 0.8068(6) 0.020(2) Uiso 1 1 d U
H16A H 0.1536 0.4319 0.7841 0.023 Uiso 1 1 calc R
H16B H 0.2395 0.4571 0.8725 0.023 Uiso 1 1 calc R
C17 C 0.1206(7) 0.5546(6) 0.6871(6) 0.032(3) Uiso 1 1 d U
H17A H 0.1178 0.6092 0.6691 0.048 Uiso 1 1 calc R
H17B H 0.0590 0.5406 0.6980 0.048 Uiso 1 1 calc R
H17C H 0.1291 0.5218 0.6397 0.048 Uiso 1 1 calc R
C18 C 0.1987(8) 0.5983(6) 0.8476(7) 0.030(3) Uiso 1 1 d U
H18A H 0.2580 0.5946 0.9001 0.044 Uiso 1 1 calc R
H18B H 0.1404 0.5835 0.8637 0.044 Uiso 1 1 calc R
H18C H 0.1911 0.6517 0.8254 0.044 Uiso 1 1 calc R
C19 C 0.5182(7) 0.5088(5) 0.6825(6) 0.022(2) Uiso 1 1 d U
C20 C 0.5726(7) 0.5749(6) 0.6499(6) 0.029(3) Uiso 1 1 d U
H20A H 0.5264 0.5999 0.5975 0.043 Uiso 1 1 calc R
H20B H 0.6283 0.5530 0.6343 0.043 Uiso 1 1 calc R
H20C H 0.5974 0.6133 0.6972 0.043 Uiso 1 1 calc R
C21 C 0.5942(7) 0.4666(5) 0.7625(6) 0.021(2) Uiso 1 1 d U
H21A H 0.6196 0.5032 0.8118 0.031 Uiso 1 1 calc R
H21B H 0.6492 0.4470 0.7443 0.031 Uiso 1 1 calc R
H21C H 0.5615 0.4232 0.7816 0.031 Uiso 1 1 calc R
C22 C 0.4714(7) 0.4533(5) 0.6021(6) 0.023(2) Uiso 1 1 d U
H22A H 0.4341 0.4123 0.6200 0.034 Uiso 1 1 calc R
H22B H 0.5240 0.4300 0.5832 0.034 Uiso 1 1 calc R
H22C H 0.4266 0.4828 0.5528 0.034 Uiso 1 1 calc R
C23 C 0.2311(7) 0.3820(5) 0.6381(7) 0.014(2) Uiso 1 1 d U
C24 C -0.2303(8) 0.4226(6) 0.5116(7) 0.037(3) Uiso 1 1 d U
H24 H -0.2489 0.4439 0.4536 0.045 Uiso 1 1 calc R
C25 C -0.1430(8) 0.4479(6) 0.5765(7) 0.038(3) Uiso 1 1 d U
H25 H -0.1019 0.4856 0.5625 0.045 Uiso 1 1 calc R
C26 C -0.1174(8) 0.4159(6) 0.6635(7) 0.034(3) Uiso 1 1 d U
H26 H -0.0583 0.4319 0.7078 0.040 Uiso 1 1 calc R
C27 C -0.1792(7) 0.3608(6) 0.6840(7) 0.032(3) Uiso 1 1 d U
H27 H -0.1631 0.3409 0.7426 0.038 Uiso 1 1 calc R
C28 C -0.2650(7) 0.3352(6) 0.6175(6) 0.031(2) Uiso 1 1 d U
H28 H -0.3059 0.2968 0.6307 0.037 Uiso 1 1 calc R
C29 C -0.2900(8) 0.3661(6) 0.5324(7) 0.037(3) Uiso 1 1 d U
H29 H -0.3481 0.3487 0.4878 0.045 Uiso 1 1 calc R
C30 C -0.1137(9) 0.2229(8) 0.4406(8) 0.056(3) Uiso 1 1 d U
H30 H -0.1439 0.2696 0.4505 0.067 Uiso 1 1 calc R
C31 C -0.0198(9) 0.2258(8) 0.4326(8) 0.056(3) Uiso 1 1 d U
H31 H 0.0121 0.2744 0.4344 0.067 Uiso 1 1 calc R
C32 C 0.0283(10) 0.1578(8) 0.4218(8) 0.061(3) Uiso 1 1 d U
H32 H 0.0932 0.1594 0.4175 0.073 Uiso 1 1 calc R
C33 C -0.0206(11) 0.0883(8) 0.4175(9) 0.067(4) Uiso 1 1 d U
H33 H 0.0115 0.0418 0.4101 0.080 Uiso 1 1 calc R
C34 C -0.1126(11) 0.0845(9) 0.4234(9) 0.071(4) Uiso 1 1 d U
H34 H -0.1437 0.0353 0.4202 0.085 Uiso 1 1 calc R
C35 C -0.1649(11) 0.1529(8) 0.4346(9) 0.073(4) Uiso 1 1 d U
H35 H -0.2302 0.1508 0.4377 0.088 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
C23 Ir1 C12 88.8(3)
C23 Ir1 C1 105.3(3)
C12 Ir1 C1 162.6(3)
C23 Ir1 C16 92.8(4)
C12 Ir1 C16 80.2(3)
C1 Ir1 C16 88.9(3)
C23 Ir1 C5 174.5(4)
C12 Ir1 C5 85.7(3)
C1 Ir1 C5 80.2(3)
C16 Ir1 C5 86.8(4)
C23 Ir1 Cl1 91.3(3)
C12 Ir1 Cl1 105.9(2)
C1 Ir1 Cl1 84.3(2)
C16 Ir1 Cl1 172.7(2)
C5 Ir1 Cl1 89.7(3)
C1 N1 C2 111.7(7)
C1 N1 C4 122.3(7)
C2 N1 C4 125.6(7)
N1 C1 N2 104.4(7)
N1 C1 Ir1 114.7(6)
N2 C1 Ir1 140.7(6)
C1 N2 C3 109.0(7)
C1 N2 C8 126.9(7)
C3 N2 C8 124.2(7)
C3 C2 N1 106.4(8)
C12 N3 C13 111.0(7)
C12 N3 C15 121.2(7)
C13 N3 C15 127.3(7)
C2 C3 N2 108.5(8)
C12 N4 C14 109.4(7)
C12 N4 C19 127.6(7)
C14 N4 C19 122.9(7)
N1 C4 C7 109.6(7)
N1 C4 C5 108.4(7)
C7 C4 C5 112.0(8)
N1 C4 C6 107.6(7)
C7 C4 C6 108.7(8)
C5 C4 C6 110.4(8)
C4 C5 Ir1 113.6(6)
N2 C8 C11 109.7(7)
N2 C8 C10 108.5(7)
C11 C8 C10 108.9(8)
N2 C8 C9 108.8(7)
C11 C8 C9 107.2(8)
C10 C8 C9 113.6(8)
N3 C12 N4 104.2(7)
N3 C12 Ir1 113.6(6)
N4 C12 Ir1 142.0(6)
C14 C13 N3 107.3(8)
C13 C14 N4 108.1(8)
N3 C15 C16 106.7(7)
N3 C15 C17 108.5(7)
C16 C15 C17 112.7(8)
N3 C15 C18 109.3(7)
C16 C15 C18 110.3(7)
C17 C15 C18 109.3(8)
C15 C16 Ir1 113.9(6)
N4 C19 C20 109.7(7)
N4 C19 C21 109.5(7)
C20 C19 C21 108.8(8)
N4 C19 C22 108.7(7)
C20 C19 C22 107.6(7)
C21 C19 C22 112.5(7)
O1 C23 Ir1 175.4(9)
C29 C24 C25 120.3(10)
C24 C25 C26 118.9(10)
C27 C26 C25 120.2(10)
C26 C27 C28 119.9(10)
C29 C28 C27 120.0(10)
C28 C29 C24 120.7(10)
C31 C30 C35 121.6(13)
C30 C31 C32 120.5(13)
C33 C32 C31 118.4(13)
C34 C33 C32 121.9(14)
C33 C34 C35 121.5(15)
C30 C35 C34 116.0(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 C23 2.008(11)
Ir1 C12 2.075(8)
Ir1 C1 2.076(8)
Ir1 C16 2.092(8)
Ir1 C5 2.130(9)
Ir1 Cl1 2.512(3)
O1 C23 0.952(10)
N1 C1 1.349(11)
N1 C2 1.379(11)
N1 C4 1.479(11)
C1 N2 1.378(11)
N2 C3 1.388(11)
N2 C8 1.503(11)
C2 C3 1.326(12)
N3 C12 1.367(11)
N3 C13 1.395(12)
N3 C15 1.477(11)
N4 C12 1.378(11)
N4 C14 1.409(11)
N4 C19 1.487(11)
C4 C7 1.533(13)
C4 C5 1.533(13)
C4 C6 1.542(13)
C8 C11 1.517(14)
C8 C10 1.527(13)
C8 C9 1.532(12)
C13 C14 1.314(12)
C15 C16 1.521(13)
C15 C17 1.526(13)
C15 C18 1.536(13)
C19 C20 1.526(13)
C19 C21 1.529(12)
C19 C22 1.532(12)
C24 C29 1.372(14)
C24 C25 1.377(14)
C25 C26 1.394(14)
C26 C27 1.374(14)
C27 C28 1.378(13)
C28 C29 1.362(14)
C30 C31 1.357(16)
C30 C35 1.369(17)
C31 C32 1.368(16)
C32 C33 1.348(17)
C33 C34 1.320(17)
C34 C35 1.408(18)
