#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:45:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178580 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/91/4069170.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_4069170
loop_
_publ_author_name
'Crestani, Marco G.'
'Steffen, Andreas'
'Kenwright, Alan M.'
'Batsanov, Andrei S.'
'Howard, Judith A. K.'
'Marder, Todd B.'
_publ_section_title
;
 Oxidative Addition of X−H (X = C, N, O) Bonds to [Ir(PMe3)4]Cl and
 Catalytic Hydration of Acetonitrile Using its Peroxo Derivative,
 [Ir(O2)(PMe3)4]Cl, as Catalyst Precursor
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              2904
_journal_paper_doi               10.1021/om9000633
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety
'C12 H37 Cl Ir P4 1+,C7 H4 N O 1-,C7 H5 N O,C4 H8 O'
_chemical_formula_sum            'C30 H54 Cl Ir N2 O3 P4'
_chemical_formula_weight         842.28
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 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                 90.595(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.0293(7)
_cell_length_b                   6.6050(3)
_cell_length_c                   21.672(1)
_cell_measurement_reflns_used    7036
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      34.97
_cell_measurement_theta_min      3.13
_cell_volume                     1864.96(16)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area detector'
_diffrn_measurement_method       'ω 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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            31651
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         34.99
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.854
_exptl_absorpt_correction_T_max  0.5488
_exptl_absorpt_correction_T_min  0.2304
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'SADABS-2006/1 (Bruker AXS), R(int)=0.095 before correction'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.158
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         7935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0187
_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)+(0.0209P)²+0.7196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0430
_reflns_number_gt                7541
_reflns_number_total             7935
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om9000633_si_002.cif
_cod_data_source_block           5b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               4069170
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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 0.7500 0.083849(9) 0.7500 0.01528(2) Uani 1 2 d S
H1 H 0.7500 0.303(5) 0.7500 0.043(9) Uiso 1 2 d S
Cl Cl 0.7500 -0.29390(7) 0.7500 0.02555(9) Uani 1 2 d S
P1 P 0.62162(3) 0.04471(5) 0.824161(16) 0.01997(6) Uani 1 1 d .
P2 P 0.62833(3) 0.15213(5) 0.673304(16) 0.01926(6) Uani 1 1 d .
O1 O 0.42687(10) 0.02964(18) 0.96563(6) 0.0342(3) Uani 1 1 d .
H01 H 0.5000 0.0000 1.0000 0.075(12) Uiso 1 2 d S
N N 0.07429(12) -0.7117(3) 0.96670(9) 0.0455(4) Uani 1 1 d .
C1 C 0.36057(13) -0.1217(2) 0.96242(7) 0.0273(3) Uani 1 1 d .
C2 C 0.25646(16) -0.0836(3) 0.94856(9) 0.0369(4) Uani 1 1 d .
H2 H 0.2352 0.0504 0.9390 0.044 Uiso 1 1 d R
C3 C 0.18496(14) -0.2359(3) 0.94858(8) 0.0364(4) Uani 1 1 d .
H3 H 0.1149 -0.2059 0.9402 0.044 Uiso 1 1 d R
C4 C 0.21426(12) -0.4351(2) 0.96079(7) 0.0265(3) Uani 1 1 d .
C5 C 0.31778(12) -0.4789(2) 0.97221(7) 0.0267(3) Uani 1 1 d .
H5 H 0.3387 -0.6149 0.9792 0.032 Uiso 1 1 d R
C6 C 0.38968(12) -0.3244(2) 0.97320(7) 0.0269(3) Uani 1 1 d .
H6 H 0.4597 -0.3554 0.9814 0.032 Uiso 1 1 d R
C7 C 0.13721(13) -0.5900(3) 0.96393(9) 0.0334(3) Uani 1 1 d .
C8 C 0.66013(13) -0.1113(2) 0.88979(7) 0.0274(3) Uani 1 1 d .
H8A H 0.6011 -0.1319 0.9168 0.039(3) Uiso 1 1 d R
H8B H 0.7152 -0.0432 0.9129 0.039(3) Uiso 1 1 d R
H8C H 0.6847 -0.2427 0.8750 0.039(3) Uiso 1 1 d R
C9 C 0.56311(11) 0.2674(2) 0.85867(7) 0.0256(3) Uani 1 1 d .
H9A H 0.5078 0.2252 0.8862 0.041(3) Uiso 1 1 d R
H9B H 0.5349 0.3545 0.8260 0.041(3) Uiso 1 1 d R
H9C H 0.6151 0.3424 0.8824 0.041(3) Uiso 1 1 d R
C10 C 0.51074(13) -0.1050(2) 0.79928(8) 0.0312(3) Uani 1 1 d .
H10A H 0.4659 -0.1295 0.8346 0.045(4) Uiso 1 1 d R
H10B H 0.5343 -0.2349 0.7827 0.045(4) Uiso 1 1 d R
H10C H 0.4725 -0.0315 0.7672 0.045(4) Uiso 1 1 d R
C11 C 0.67325(12) 0.3131(2) 0.61097(7) 0.0259(3) Uani 1 1 d .
H11A H 0.6154 0.3479 0.5836 0.038(3) Uiso 1 1 d R
H11B H 0.7256 0.2411 0.5873 0.038(3) Uiso 1 1 d R
H11C H 0.7029 0.4374 0.6283 0.038(3) Uiso 1 1 d R
C12 C 0.52361(12) 0.3171(3) 0.69703(7) 0.0290(3) Uani 1 1 d .
H12A H 0.4808 0.3514 0.6610 0.037(3) Uiso 1 1 d R
H12B H 0.5521 0.4415 0.7150 0.037(3) Uiso 1 1 d R
H12C H 0.4817 0.2477 0.7278 0.037(3) Uiso 1 1 d R
C13 C 0.56347(14) -0.0544(2) 0.63315(8) 0.0311(3) Uani 1 1 d .
H13A H 0.5202 0.0006 0.5999 0.061(5) Uiso 1 1 d R
H13B H 0.5206 -0.1291 0.6623 0.061(5) Uiso 1 1 d R
H13C H 0.6147 -0.1460 0.6157 0.061(5) Uiso 1 1 d R
O2 O 0.2500 0.2528(13) 0.7500 0.195(3) Uani 1 2 d S
C16 C 0.2617(3) 0.3404(14) 0.80185(18) 0.176(4) Uani 1 1 d .
H16A H 0.3290 0.3172 0.8188 0.211 Uiso 1 1 d R
H16B H 0.2110 0.2972 0.8309 0.211 Uiso 1 1 d R
C17 C 0.2481(6) 0.5662(12) 0.7820(3) 0.180(4) Uani 1 1 d .
H17A H 0.3000 0.6505 0.8004 0.216 Uiso 1 1 d R
H17B H 0.1819 0.6141 0.7944 0.216 Uiso 1 1 d 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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 -1.00 0.0650
-1.00 0.00 1.00 0.0650
2.00 6.00 3.00 0.1300
-2.00 -6.00 -3.00 0.1300
0.00 0.00 1.00 0.1500
0.00 0.00 -1.00 0.1500
-2.00 0.00 -1.00 0.1550
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
P2 Ir P2 157.670(18) 2_656 .
P2 Ir P1 91.456(13) 2_656 2_656
P2 Ir P1 90.990(13) . 2_656
P2 Ir P1 90.991(13) 2_656 .
P2 Ir P1 91.454(13) . .
P1 Ir P1 167.347(18) 2_656 .
P2 Ir Cl 101.165(9) 2_656 .
P2 Ir Cl 101.165(9) . .
P1 Ir Cl 83.673(9) 2_656 .
P1 Ir Cl 83.674(9) . .
P2 Ir H1 78.835(17) 2_656 .
P2 Ir H1 78.835(9) . .
P1 Ir H1 96.327(19) 2_656 .
P1 Ir H1 96.326(10) . .
Cl Ir H1 180.00(2) . .
C9 P1 C8 104.43(7) . .
C9 P1 C10 103.02(8) . .
C8 P1 C10 97.75(8) . .
C9 P1 Ir 119.79(5) . .
C8 P1 Ir 113.86(5) . .
C10 P1 Ir 115.12(6) . .
C11 P2 C13 103.54(8) . .
C11 P2 C12 96.16(7) . .
C13 P2 C12 103.74(8) . .
C11 P2 Ir 114.89(5) . .
C13 P2 Ir 120.33(6) . .
C12 P2 Ir 114.84(5) . .
C1 O1 H01 114.6 . .
O1 C1 C2 120.21(14) . .
O1 C1 C6 122.30(15) . .
C2 C1 C6 117.49(15) . .
C3 C2 C1 121.43(15) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.4 . .
C2 C3 C4 120.51(16) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.6 . .
C3 C4 C5 119.35(16) . .
C3 C4 C7 119.42(15) . .
C5 C4 C7 121.18(14) . .
C6 C5 C4 120.05(14) . .
C6 C5 H5 120.1 . .
C4 C5 H5 119.8 . .
C5 C6 C1 121.08(15) . .
C5 C6 H6 119.5 . .
C1 C6 H6 119.5 . .
N C7 C4 178.88(19) . .
P1 C8 H8A 109.4 . .
P1 C8 H8B 109.5 . .
H8A C8 H8B 109.4 . .
P1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.4 . .
P1 C9 H9A 109.5 . .
P1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
P1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
P1 C10 H10A 109.6 . .
P1 C10 H10B 109.4 . .
H10A C10 H10B 109.4 . .
P1 C10 H10C 109.7 . .
H10A C10 H10C 109.4 . .
H10B C10 H10C 109.4 . .
P2 C11 H11A 109.5 . .
P2 C11 H11B 109.6 . .
H11A C11 H11B 109.4 . .
P2 C11 H11C 109.5 . .
H11A C11 H11C 109.4 . .
H11B C11 H11C 109.4 . .
P2 C12 H12A 109.5 . .
P2 C12 H12B 109.4 . .
H12A C12 H12B 109.4 . .
P2 C12 H12C 109.6 . .
H12A C12 H12C 109.4 . .
H12B C12 H12C 109.4 . .
P2 C13 H13A 109.5 . .
P2 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
P2 C13 H13C 109.4 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C16 O2 C16 125.9(11) . 2_556
O2 C16 C17 100.3(5) . .
O2 C16 H16A 111.4 . .
C17 C16 H16A 111.0 . .
O2 C16 H16B 111.6 . .
C17 C16 H16B 112.8 . .
H16A C16 H16B 109.5 . .
C17 C17 C16 105.7(3) 2_556 .
C17 C17 H17A 112.5 2_556 .
C16 C17 H17A 111.2 . .
C17 C17 H17B 108.8 2_556 .
C16 C17 H17B 109.7 . .
H17A C17 H17B 108.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir P2 2.3290(4) 2_656
Ir P2 2.3291(4) .
Ir P1 2.3460(4) 2_656
Ir P1 2.3460(4) .
Ir Cl 2.4950(5) .
Ir H1 1.45(3) .
P1 C9 1.8211(15) .
P1 C8 1.8224(15) .
P1 C10 1.8273(16) .
P2 C11 1.8207(15) .
P2 C13 1.8213(15) .
P2 C12 1.8243(16) .
O1 C1 1.323(2) .
O1 H01 1.22 .
N C7 1.150(3) .
C1 C2 1.409(3) .
C1 C6 1.410(2) .
C2 C3 1.371(3) .
C2 H2 0.9500 .
C3 C4 1.395(2) .
C3 H3 0.9502 .
C4 C5 1.399(2) .
C4 C7 1.435(2) .
C5 C6 1.385(2) .
C5 H5 0.9500 .
C6 H6 0.9498 .
C8 H8A 0.9803 .
C8 H8B 0.9804 .
C8 H8C 0.9804 .
C9 H9A 0.9803 .
C9 H9B 0.9799 .
C9 H9C 0.9797 .
C10 H10A 0.9810 .
C10 H10B 0.9806 .
C10 H10C 0.9806 .
C11 H11A 0.9808 .
C11 H11B 0.9806 .
C11 H11C 0.9804 .
C12 H12A 0.9804 .
C12 H12B 0.9806 .
C12 H12C 0.9802 .
C13 H13A 0.9805 .
C13 H13B 0.9802 .
C13 H13C 0.9801 .
O2 C16 1.272(7) .
O2 C16 1.272(7) 2_556
C16 C17 1.561(10) .
C16 H16A 0.9599 .
C16 H16B 0.9599 .
C17 C17 1.388(11) 2_556
C17 H17A 0.9599 .
C17 H17B 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H01 O1 1.219 1.219 2.438(3) 180.00 3_657
