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#$Date: 2016-03-21 07:44:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178579 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/89/4068996.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_4068996
loop_
_publ_author_name
'Esteruelas, Miguel A.'
'Fernández-Alvarez, Francisco J.'
'Oliván, Montserrat'
'Oñate, Enrique'
_publ_section_title
;
 NH-Tautomerization of Quinolines and 2-Methylpyridine Promoted by a
 Hydride-Iridium(III) Complex: Importance of the Hydride Ligand
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              2276
_journal_paper_doi               10.1021/om8011954
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C25 H52 Cl4 Ir N P2'
_chemical_formula_weight         762.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.365(9)
_cell_length_b                   12.868(5)
_cell_length_c                   10.606(4)
_cell_measurement_reflns_used    824
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2.5
_cell_volume                     3189(2)
_computing_cell_refinement       'SAINT+ v. 6.1 (Bruker AXS, 2000)'
_computing_data_collection       'SMART v. 5.625 (Bruker AXS, 2000)'
_computing_data_reduction        'SAINT+ v. 6.1 (Bruker AXS, 2000)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.1 (Bruker, 2000)'
_computing_publication_material  'XCIF, SHELXTL v. 6.1 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker SMART APEX CCD system'
_diffrn_measurement_method       'ω rotations with narrow frames'
_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  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20281
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.91
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        'no decay'
_exptl_absorpt_coefficient_mu    4.638
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Absorption correction performed with SADABS program. This is based on the
method of Blessing: Blessing, R. H., Acta Crystallogr., Sect. A 1995, 51, 33.

SADABS: Area-Detector Absorption Correction. Bruker-AXS 
within SAINT+ package, v. 6.1 (2000).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.161
_refine_diff_density_min         -1.963
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0282P)²+19.4133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                3409
_reflns_number_total             4026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om8011954_si_001.cif
_cod_data_source_block           mae335as
_cod_original_sg_symbol_H-M      'P nma'
_cod_database_code               4068996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
Ir Ir 0.889204(12) 0.7500 0.76733(3) 0.03260(12) Uani 1 2 d SD
H01 H 0.836(2) 0.7500 0.678(7) 0.039 Uiso 1 2 d SD
Cl1 Cl 0.98132(8) 0.7500 0.90114(18) 0.0404(6) Uani 1 2 d S
Cl2 Cl 0.94627(8) 0.7500 0.57362(17) 0.0395(6) Uani 1 2 d S
Cl3 Cl 0.86241(10) 0.1399(3) 0.3217(5) 0.1483(19) Uani 1 1 d .
P1 P 0.88119(6) 0.93217(16) 0.74627(13) 0.0380(4) Uani 1 1 d .
N1 N 0.8717(3) 0.7500 1.0370(6) 0.0271(16) Uani 1 2 d S
H1 H 0.906(4) 0.7500 1.030(9) 0.035 Uiso 1 2 d S
C1 C 0.8431(3) 0.7500 0.9261(7) 0.0286(19) Uani 1 2 d S
C2 C 0.7832(3) 0.7500 0.9431(8) 0.039(2) Uani 1 2 d S
H2 H 0.7594 0.7500 0.8705 0.047 Uiso 1 2 calc SR
C3 C 0.7579(3) 0.7500 1.0590(8) 0.034(2) Uani 1 2 d S
H3 H 0.7174 0.7500 1.0656 0.041 Uiso 1 2 calc SR
C4 C 0.7916(4) 0.7500 1.1683(7) 0.035(2) Uani 1 2 d S
H4 H 0.7744 0.7500 1.2495 0.041 Uiso 1 2 calc SR
C5 C 0.8503(4) 0.7500 1.1549(8) 0.035(2) Uani 1 2 d S
C6 C 0.8924(5) 0.7500 1.2601(8) 0.065(4) Uani 1 2 d S
H6A H 0.9093 0.6806 1.2685 0.097 Uiso 0.50 1 calc PR
H6B H 0.8731 0.7688 1.3388 0.097 Uiso 0.50 1 calc PR
H6C H 0.9227 0.8006 1.2423 0.097 Uiso 0.50 1 calc PR
C7 C 0.9426(3) 0.9989(7) 0.6688(6) 0.0440(18) Uani 1 1 d .
H7 H 0.9460 0.9654 0.5841 0.053 Uiso 1 1 calc R
C8 C 0.9998(3) 0.9792(11) 0.7324(9) 0.102(5) Uani 1 1 d .
H8A H 1.0308 0.9940 0.6730 0.122 Uiso 1 1 calc R
H8B H 1.0019 0.9064 0.7591 0.122 Uiso 1 1 calc R
H8C H 1.0034 1.0246 0.8062 0.122 Uiso 1 1 calc R
C9 C 0.9357(3) 1.1129(7) 0.6418(9) 0.061(2) Uani 1 1 d .
H9A H 0.9372 1.1520 0.7210 0.091 Uiso 1 1 calc R
H9B H 0.8987 1.1249 0.6007 0.091 Uiso 1 1 calc R
H9C H 0.9666 1.1362 0.5860 0.091 Uiso 1 1 calc R
C10 C 0.8214(2) 0.9689(7) 0.6392(6) 0.0438(18) Uani 1 1 d .
H10 H 0.8219 1.0463 0.6302 0.053 Uiso 1 1 calc R
C11 C 0.8288(3) 0.9221(8) 0.5072(6) 0.057(2) Uani 1 1 d .
H11A H 0.8263 0.8462 0.5125 0.086 Uiso 1 1 calc R
H11B H 0.8662 0.9418 0.4733 0.086 Uiso 1 1 calc R
H11C H 0.7986 0.9482 0.4516 0.086 Uiso 1 1 calc R
C12 C 0.7624(3) 0.9378(7) 0.6910(6) 0.0464(19) Uani 1 1 d .
H12A H 0.7324 0.9701 0.6397 0.070 Uiso 1 1 calc R
H12B H 0.7589 0.9614 0.7785 0.070 Uiso 1 1 calc R
H12C H 0.7584 0.8620 0.6878 0.070 Uiso 1 1 calc R
C13 C 0.8622(3) 1.0005(6) 0.8949(6) 0.0405(17) Uani 1 1 d .
H13 H 0.8311 0.9582 0.9342 0.049 Uiso 1 1 calc R
C14 C 0.9118(3) 0.9995(6) 0.9903(6) 0.0472(18) Uani 1 1 d .
H14A H 0.9395 1.0538 0.9682 0.071 Uiso 1 1 calc R
H14B H 0.9308 0.9316 0.9883 0.071 Uiso 1 1 calc R
H14C H 0.8969 1.0125 1.0751 0.071 Uiso 1 1 calc R
C15 C 0.8382(3) 1.1104(7) 0.8835(7) 0.057(2) Uani 1 1 d .
H15A H 0.8247 1.1339 0.9662 0.086 Uiso 1 1 calc R
H15B H 0.8062 1.1106 0.8237 0.086 Uiso 1 1 calc R
H15C H 0.8683 1.1574 0.8533 0.086 Uiso 1 1 calc R
C16 C 0.9043(4) 0.2500 0.3032(11) 0.073(4) Uani 1 2 d S
H16A H 0.9354 0.2500 0.3666 0.088 Uiso 1 2 calc SR
H16B H 0.9219 0.2500 0.2183 0.088 Uiso 1 2 calc SR
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'
P P 0.1023 0.0942 '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
C1 Ir P1 92.11(4) . 7_575
C1 Ir P1 92.12(4) . .
P1 Ir P1 165.82(7) 7_575 .
C1 Ir Cl2 179.6(2) . .
P1 Ir Cl2 87.93(4) 7_575 .
P1 Ir Cl2 87.93(4) . .
C1 Ir Cl1 89.2(2) . .
P1 Ir Cl1 96.79(4) 7_575 .
P1 Ir Cl1 96.79(4) . .
Cl2 Ir Cl1 90.42(7) . .
C1 Ir H01 94(3) . .
P1 Ir H01 83.09(12) 7_575 .
P1 Ir H01 83.09(10) . .
Cl2 Ir H01 86(3) . .
Cl1 Ir H01 176(3) . .
C13 P1 C10 102.6(3) . .
C13 P1 C7 109.8(3) . .
C10 P1 C7 101.1(3) . .
C13 P1 Ir 114.1(3) . .
C10 P1 Ir 111.7(3) . .
C7 P1 Ir 116.0(3) . .
C5 N1 C1 128.5(7) . .
C5 N1 H1 117(7) . .
C1 N1 H1 114(7) . .
N1 C1 C2 112.3(7) . .
N1 C1 Ir 117.7(5) . .
C2 C1 Ir 130.0(6) . .
C3 C2 C1 123.0(8) . .
C3 C2 H2 118.5 . .
C1 C2 H2 118.5 . .
C2 C3 C4 120.2(8) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 118.3(7) . .
C5 C4 H4 120.9 . .
C3 C4 H4 120.9 . .
N1 C5 C4 117.7(8) . .
N1 C5 C6 116.8(8) . .
C4 C5 C6 125.5(8) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C9 C7 C8 110.0(8) . .
C9 C7 P1 116.8(5) . .
C8 C7 P1 113.9(5) . .
C9 C7 H7 105.0 . .
C8 C7 H7 105.0 . .
P1 C7 H7 105.0 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 C12 108.9(6) . .
C11 C10 P1 111.9(5) . .
C12 C10 P1 112.9(5) . .
C11 C10 H10 107.6 . .
C12 C10 H10 107.6 . .
P1 C10 H10 107.6 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C15 C13 C14 109.7(6) . .
C15 C13 P1 117.3(5) . .
C14 C13 P1 112.0(5) . .
C15 C13 H13 105.6 . .
C14 C13 H13 105.6 . .
P1 C13 H13 105.6 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
Cl3 C16 Cl3 109.7(6) 7_565 .
Cl3 C16 H16A 109.7 7_565 .
Cl3 C16 H16A 109.7 . .
Cl3 C16 H16B 109.7 7_565 .
Cl3 C16 H16B 109.7 . .
H16A C16 H16B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir C1 1.999(8) .
Ir P1 2.362(2) 7_575
Ir P1 2.362(2) .
Ir Cl2 2.449(2) .
Ir Cl1 2.578(2) .
Ir H01 1.57(2) .
Cl3 C16 1.732(7) .
P1 C13 1.858(7) .
P1 C10 1.861(6) .
P1 C7 1.864(6) .
N1 C5 1.347(10) .
N1 C1 1.353(10) .
N1 H1 0.79(10) .
C1 C2 1.411(10) .
C2 C3 1.363(11) .
C2 H2 0.9500 .
C3 C4 1.401(12) .
C3 H3 0.9500 .
C4 C5 1.379(11) .
C4 H4 0.9500 .
C5 C6 1.488(13) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C9 1.504(11) .
C7 C8 1.516(10) .
C7 H7 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.534(9) .
C10 C12 1.536(8) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C15 1.526(11) .
C13 C14 1.539(9) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 Cl3 1.732(7) 7_565
C16 H16A 0.9900 .
C16 H16B 0.9900 .
