# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_dm12587_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H30 Cl Ir N O3 P'
_chemical_formula_weight         579.06

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0810(8)
_cell_length_b                   8.7266(8)
_cell_length_c                   15.7699(15)
_cell_angle_alpha                79.849(2)
_cell_angle_beta                 79.048(2)
_cell_angle_gamma                79.265(2)
_cell_volume                     1061.23(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    5149
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.81

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    6.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3559
_exptl_absorpt_correction_T_max  0.8287
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10752
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         30.90
_reflns_number_total             6602
_reflns_number_gt                5923
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0212P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6602
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0611
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.198626(15) 0.476794(14) 0.309294(8) 0.01280(4) Uani 1 1 d . . .
H1M H 0.341(5) 0.588(5) 0.264(3) 0.029(12) Uiso 1 1 d . . .
Cl1 Cl 0.05753(12) 0.67451(10) 0.40632(5) 0.02154(17) Uani 1 1 d . . .
N1 N 0.3687(4) 0.3418(3) 0.39528(19) 0.0177(6) Uani 1 1 d . . .
O1 O 0.1956(3) 0.4495(3) 0.11669(15) 0.0162(5) Uani 1 1 d . . .
O2 O 0.0073(3) 0.3274(3) 0.39013(16) 0.0191(5) Uani 1 1 d . . .
H21 H 0.0220 0.3369 0.4408 0.029 Uiso 1 1 d R . .
H22 H 0.0686 0.2369 0.3903 0.029 Uiso 1 1 d R . .
O3 O 0.1284(4) 1.0268(3) 0.3542(2) 0.0366(7) Uani 1 1 d . . .
H31 H 0.2313 1.0427 0.3395 0.055 Uiso 1 1 d R . .
H32 H 0.1547 0.9271 0.3593 0.055 Uiso 1 1 d R . .
P1 P 0.08313(10) 0.56183(10) 0.18959(5) 0.01291(15) Uani 1 1 d . . .
C1 C 0.3801(5) 0.3678(4) 0.4749(2) 0.0221(7) Uani 1 1 d . . .
H1 H 0.3030 0.4509 0.4994 0.027 Uiso 1 1 calc R . .
C2 C 0.4987(5) 0.2788(5) 0.5226(3) 0.0287(8) Uani 1 1 d . . .
H2 H 0.5007 0.2978 0.5799 0.034 Uiso 1 1 calc R . .
C3 C 0.6162(5) 0.1608(5) 0.4862(3) 0.0302(9) Uani 1 1 d . . .
H3 H 0.7043 0.1024 0.5164 0.036 Uiso 1 1 calc R . .
C4 C 0.6018(5) 0.1301(5) 0.4048(3) 0.0266(8) Uani 1 1 d . . .
H4 H 0.6776 0.0469 0.3798 0.032 Uiso 1 1 calc R . .
C5 C 0.4769(4) 0.2207(4) 0.3598(2) 0.0190(7) Uani 1 1 d . . .
C6 C 0.4550(4) 0.2040(4) 0.2724(2) 0.0173(6) Uani 1 1 d . . .
C7 C 0.5473(4) 0.0896(4) 0.2222(3) 0.0217(7) Uani 1 1 d . . .
H7 H 0.6272 0.0074 0.2465 0.026 Uiso 1 1 calc R . .
C8 C 0.5223(4) 0.0962(4) 0.1372(3) 0.0221(7) Uani 1 1 d . . .
H8 H 0.5865 0.0185 0.1035 0.027 Uiso 1 1 calc R . .
C9 C 0.4042(4) 0.2152(4) 0.0999(2) 0.0197(7) Uani 1 1 d . . .
H9 H 0.3890 0.2198 0.0411 0.024 Uiso 1 1 calc R . .
C10 C 0.3106(4) 0.3252(4) 0.1503(2) 0.0162(6) Uani 1 1 d . . .
C11 C 0.3299(4) 0.3199(4) 0.2377(2) 0.0155(6) Uani 1 1 d . . .
C12 C 0.1101(4) 0.7599(4) 0.1270(2) 0.0177(6) Uani 1 1 d . . .
C13 C 0.2926(5) 0.7913(5) 0.1318(3) 0.0312(9) Uani 1 1 d . . .
H13A H 0.3140 0.8901 0.0942 0.047 Uiso 1 1 calc R . .
H13B H 0.3782 0.7042 0.1120 0.047 Uiso 1 1 calc R . .
H13C H 0.2996 0.7994 0.1922 0.047 Uiso 1 1 calc R . .
C14 C 0.0992(5) 0.7734(5) 0.0295(2) 0.0250(8) Uani 1 1 d . . .
H14A H -0.0177 0.7676 0.0231 0.038 Uiso 1 1 calc R . .
H14B H 0.1778 0.6868 0.0046 0.038 Uiso 1 1 calc R . .
H14C H 0.1304 0.8743 -0.0012 0.038 Uiso 1 1 calc R . .
C15 C -0.0214(5) 0.8849(4) 0.1702(3) 0.0271(8) Uani 1 1 d . . .
H15A H 0.0082 0.9897 0.1464 0.041 Uiso 1 1 calc R . .
H15B H -0.0218 0.8656 0.2333 0.041 Uiso 1 1 calc R . .
H15C H -0.1349 0.8797 0.1585 0.041 Uiso 1 1 calc R . .
C16 C -0.1375(4) 0.5173(4) 0.1928(2) 0.0186(6) Uani 1 1 d . . .
C17 C -0.1192(5) 0.3365(5) 0.2037(3) 0.0254(8) Uani 1 1 d . . .
H17A H -0.2326 0.3055 0.2133 0.038 Uiso 1 1 calc R . .
H17B H -0.0622 0.2900 0.2540 0.038 Uiso 1 1 calc R . .
H17C H -0.0513 0.2988 0.1509 0.038 Uiso 1 1 calc R . .
C18 C -0.2539(4) 0.5780(5) 0.2725(3) 0.0248(8) Uani 1 1 d . . .
H18A H -0.2712 0.6935 0.2636 0.037 Uiso 1 1 calc R . .
H18B H -0.2008 0.5375 0.3246 0.037 Uiso 1 1 calc R . .
H18C H -0.3643 0.5418 0.2803 0.037 Uiso 1 1 calc R . .
C19 C -0.2184(5) 0.5826(5) 0.1114(3) 0.0266(8) Uani 1 1 d . . .
H19A H -0.3230 0.5384 0.1155 0.040 Uiso 1 1 calc R . .
H19B H -0.1381 0.5537 0.0596 0.040 Uiso 1 1 calc R . .
H19C H -0.2459 0.6977 0.1066 0.040 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C11 1.955(3) . ?
Ir1 N1 2.158(3) . ?
Ir1 P1 2.2143(8) . ?
Ir1 O2 2.266(2) . ?
Ir1 Cl1 2.4806(9) . ?
Ir1 H1M 1.62(4) . ?
N1 C1 1.338(5) . ?
N1 C5 1.369(5) . ?
O1 C10 1.390(4) . ?
O1 P1 1.666(2) . ?
O2 H21 0.8500 . ?
O2 H22 0.8500 . ?
O3 H31 0.8500 . ?
O3 H32 0.8500 . ?
P1 C12 1.861(3) . ?
P1 C16 1.884(4) . ?
C1 C2 1.370(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.458(5) . ?
C6 C7 1.399(5) . ?
C6 C11 1.406(4) . ?
C7 C8 1.382(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.408(5) . ?
C12 C15 1.529(5) . ?
C12 C14 1.540(5) . ?
C12 C13 1.567(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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 C19 1.525(5) . ?
C16 C18 1.531(5) . ?
C16 C17 1.539(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
_geom_angle_publ_flag
C11 Ir1 N1 78.49(12) . . ?
C11 Ir1 P1 81.54(10) . . ?
N1 Ir1 P1 159.85(8) . . ?
C11 Ir1 O2 98.00(11) . . ?
N1 Ir1 O2 84.10(10) . . ?
P1 Ir1 O2 101.37(7) . . ?
C11 Ir1 Cl1 174.42(10) . . ?
N1 Ir1 Cl1 96.78(8) . . ?
P1 Ir1 Cl1 103.02(3) . . ?
O2 Ir1 Cl1 84.34(7) . . ?
C11 Ir1 H1M 86.8(15) . . ?
N1 Ir1 H1M 90.7(16) . . ?
P1 Ir1 H1M 85.5(16) . . ?
O2 Ir1 H1M 172.1(16) . . ?
Cl1 Ir1 H1M 90.4(15) . . ?
C1 N1 C5 119.5(3) . . ?
C1 N1 Ir1 127.2(2) . . ?
C5 N1 Ir1 113.3(2) . . ?
C10 O1 P1 114.5(2) . . ?
Ir1 O2 H21 99.0 . . ?
Ir1 O2 H22 99.4 . . ?
H21 O2 H22 94.0 . . ?
H31 O3 H32 94.0 . . ?
O1 P1 C12 99.41(14) . . ?
O1 P1 C16 100.46(14) . . ?
C12 P1 C16 111.42(15) . . ?
O1 P1 Ir1 104.83(9) . . ?
C12 P1 Ir1 120.05(12) . . ?
C16 P1 Ir1 116.58(11) . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.0(3) . . ?
N1 C5 C6 115.0(3) . . ?
C4 C5 C6 125.0(3) . . ?
C7 C6 C11 119.7(3) . . ?
C7 C6 C5 126.4(3) . . ?
C11 C6 C5 113.9(3) . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 O1 121.6(3) . . ?
C9 C10 C11 121.8(3) . . ?
O1 C10 C11 116.6(3) . . ?
C6 C11 C10 118.7(3) . . ?
C6 C11 Ir1 119.3(3) . . ?
C10 C11 Ir1 121.9(2) . . ?
C15 C12 C14 111.1(3) . . ?
C15 C12 C13 108.2(3) . . ?
C14 C12 C13 106.6(3) . . ?
C15 C12 P1 109.1(2) . . ?
C14 C12 P1 113.5(2) . . ?
C13 C12 P1 108.2(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C16 C18 109.6(3) . . ?
C19 C16 C17 107.2(3) . . ?
C18 C16 C17 109.7(3) . . ?
C19 C16 P1 116.0(2) . . ?
C18 C16 P1 108.4(2) . . ?
C17 C16 P1 105.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 Ir1 N1 C1 177.9(3) . . . . ?
P1 Ir1 N1 C1 170.2(2) . . . . ?
O2 Ir1 N1 C1 -82.7(3) . . . . ?
Cl1 Ir1 N1 C1 0.8(3) . . . . ?
C11 Ir1 N1 C5 -0.2(2) . . . . ?
P1 Ir1 N1 C5 -7.9(4) . . . . ?
O2 Ir1 N1 C5 99.2(2) . . . . ?
Cl1 Ir1 N1 C5 -177.2(2) . . . . ?
C10 O1 P1 C12 132.4(2) . . . . ?
C10 O1 P1 C16 -113.6(2) . . . . ?
C10 O1 P1 Ir1 7.8(2) . . . . ?
C11 Ir1 P1 O1 -5.39(13) . . . . ?
N1 Ir1 P1 O1 2.2(2) . . . . ?
O2 Ir1 P1 O1 -101.91(11) . . . . ?
Cl1 Ir1 P1 O1 171.34(9) . . . . ?
C11 Ir1 P1 C12 -115.79(16) . . . . ?
N1 Ir1 P1 C12 -108.2(3) . . . . ?
O2 Ir1 P1 C12 147.69(14) . . . . ?
Cl1 Ir1 P1 C12 60.94(13) . . . . ?
C11 Ir1 P1 C16 104.64(16) . . . . ?
N1 Ir1 P1 C16 112.2(3) . . . . ?
O2 Ir1 P1 C16 8.12(14) . . . . ?
Cl1 Ir1 P1 C16 -78.63(13) . . . . ?
C5 N1 C1 C2 1.1(5) . . . . ?
Ir1 N1 C1 C2 -176.8(3) . . . . ?
N1 C1 C2 C3 2.4(6) . . . . ?
C1 C2 C3 C4 -4.2(6) . . . . ?
C2 C3 C4 C5 2.7(6) . . . . ?
C1 N1 C5 C4 -2.7(5) . . . . ?
Ir1 N1 C5 C4 175.6(3) . . . . ?
C1 N1 C5 C6 -179.3(3) . . . . ?
Ir1 N1 C5 C6 -1.1(4) . . . . ?
C3 C4 C5 N1 0.7(6) . . . . ?
C3 C4 C5 C6 177.0(3) . . . . ?
N1 C5 C6 C7 -179.3(3) . . . . ?
C4 C5 C6 C7 4.3(6) . . . . ?
N1 C5 C6 C11 2.4(4) . . . . ?
C4 C5 C6 C11 -174.1(3) . . . . ?
C11 C6 C7 C8 3.7(5) . . . . ?
C5 C6 C7 C8 -174.6(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C9 C10 O1 177.8(3) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
P1 O1 C10 C9 175.3(3) . . . . ?
P1 O1 C10 C11 -6.3(4) . . . . ?
C7 C6 C11 C10 -5.2(5) . . . . ?
C5 C6 C11 C10 173.3(3) . . . . ?
C7 C6 C11 Ir1 178.8(2) . . . . ?
C5 C6 C11 Ir1 -2.7(4) . . . . ?
C9 C10 C11 C6 3.6(5) . . . . ?
O1 C10 C11 C6 -174.8(3) . . . . ?
C9 C10 C11 Ir1 179.5(3) . . . . ?
O1 C10 C11 Ir1 1.1(4) . . . . ?
N1 Ir1 C11 C6 1.6(3) . . . . ?
P1 Ir1 C11 C6 178.9(3) . . . . ?
O2 Ir1 C11 C6 -80.7(3) . . . . ?
Cl1 Ir1 C11 C6 33.8(11) . . . . ?
N1 Ir1 C11 C10 -174.3(3) . . . . ?
P1 Ir1 C11 C10 3.1(3) . . . . ?
O2 Ir1 C11 C10 103.5(3) . . . . ?
Cl1 Ir1 C11 C10 -142.0(8) . . . . ?
O1 P1 C12 C15 164.7(2) . . . . ?
C16 P1 C12 C15 59.5(3) . . . . ?
Ir1 P1 C12 C15 -82.0(3) . . . . ?
O1 P1 C12 C14 40.3(3) . . . . ?
C16 P1 C12 C14 -65.0(3) . . . . ?
Ir1 P1 C12 C14 153.6(2) . . . . ?
O1 P1 C12 C13 -77.8(3) . . . . ?
C16 P1 C12 C13 177.0(3) . . . . ?
Ir1 P1 C12 C13 35.5(3) . . . . ?
O1 P1 C16 C19 -70.0(3) . . . . ?
C12 P1 C16 C19 34.6(3) . . . . ?
Ir1 P1 C16 C19 177.5(2) . . . . ?
O1 P1 C16 C18 166.3(2) . . . . ?
C12 P1 C16 C18 -89.1(3) . . . . ?
Ir1 P1 C16 C18 53.8(3) . . . . ?
O1 P1 C16 C17 48.7(2) . . . . ?
C12 P1 C16 C17 153.2(2) . . . . ?
Ir1 P1 C16 C17 -63.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        30.90
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.895
_refine_diff_density_min         -1.101
_refine_diff_density_rms         0.154
_database_code_depnum_ccdc_archive 'CCDC 957716'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_dm12657_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 Cl Ir N O P'
_chemical_formula_weight         557.05

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   10.1303(10)
_cell_length_b                   13.7700(14)
_cell_length_c                   15.0040(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.782(2)
_cell_angle_gamma                90.00
_cell_volume                     2014.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9615
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      30.54

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    6.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2331
_exptl_absorpt_correction_T_max  0.4070
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19210
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         30.60
_reflns_number_total             6175
_reflns_number_gt                5127
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.9757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6175
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0544
_refine_ls_wR_factor_gt          0.0511
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.257854(9) 0.667313(7) 0.080833(6) 0.01493(3) Uani 1 1 d . . .
H1M H 0.1835 0.6649 0.0092 0.022 Uiso 1 1 d R . .
Cl1 Cl 0.48364(6) 0.66707(5) 0.18486(5) 0.02488(13) Uani 1 1 d . . .
N1 N 0.2180(2) 0.51911(17) 0.11252(15) 0.0208(5) Uani 1 1 d . . .
O1 O 0.05616(19) 0.83905(14) 0.03017(14) 0.0204(4) Uani 1 1 d . . .
P1 P 0.22401(6) 0.82373(5) 0.04501(5) 0.01460(12) Uani 1 1 d . . .
C1 C 0.0659(3) 0.67566(19) 0.08266(18) 0.0166(5) Uani 1 1 d . . .
C2 C -0.0077(3) 0.7616(2) 0.06076(19) 0.0195(5) Uani 1 1 d . . .
C3 C -0.1390(3) 0.7704(2) 0.0712(2) 0.0256(6) Uani 1 1 d . . .
H3 H -0.1893 0.8291 0.0558 0.031 Uiso 1 1 calc R . .
C4 C -0.1955(3) 0.6903(3) 0.1052(2) 0.0310(7) Uani 1 1 d . . .
H4 H -0.2850 0.6954 0.1133 0.037 Uiso 1 1 calc R . .
C5 C -0.1245(3) 0.6042(2) 0.1273(2) 0.0275(6) Uani 1 1 d . . .
H5 H -0.1651 0.5508 0.1501 0.033 Uiso 1 1 calc R . .
C6 C 0.0083(3) 0.5957(2) 0.11576(18) 0.0205(5) Uani 1 1 d . . .
C7 C 0.0967(3) 0.5096(2) 0.13488(17) 0.0219(5) Uani 1 1 d . . .
C8 C 0.0635(4) 0.4236(2) 0.1726(2) 0.0310(7) Uani 1 1 d . . .
H8 H -0.0192 0.4186 0.1906 0.037 Uiso 1 1 calc R . .
C9 C 0.1522(4) 0.3459(2) 0.1836(2) 0.0390(9) Uani 1 1 d . . .
H9 H 0.1332 0.2878 0.2119 0.047 Uiso 1 1 calc R . .
C10 C 0.2685(4) 0.3531(2) 0.1534(3) 0.0368(8) Uani 1 1 d . . .
H10 H 0.3277 0.2987 0.1577 0.044 Uiso 1 1 calc R . .
C11 C 0.2989(3) 0.4404(2) 0.1165(2) 0.0256(6) Uani 1 1 d . . .
C12 C 0.4176(3) 0.4498(2) 0.0761(3) 0.0343(7) Uani 1 1 d . . .
H12A H 0.3856 0.4754 0.0129 0.052 Uiso 1 1 calc R . .
H12B H 0.4598 0.3860 0.0747 0.052 Uiso 1 1 calc R . .
H12C H 0.4855 0.4944 0.1141 0.052 Uiso 1 1 calc R . .
C13 C 0.2495(3) 0.8625(2) -0.06827(17) 0.0182(5) Uani 1 1 d . . .
C14 C 0.1381(3) 0.8121(2) -0.1449(2) 0.0276(6) Uani 1 1 d . . .
H14A H 0.0481 0.8392 -0.1463 0.041 Uiso 1 1 calc R . .
H14B H 0.1387 0.7423 -0.1324 0.041 Uiso 1 1 calc R . .
H14C H 0.1566 0.8229 -0.2050 0.041 Uiso 1 1 calc R . .
C15 C 0.2387(3) 0.9717(2) -0.0867(2) 0.0245(6) Uani 1 1 d . . .
H15A H 0.3126 1.0051 -0.0412 0.037 Uiso 1 1 calc R . .
H15B H 0.1498 0.9952 -0.0816 0.037 Uiso 1 1 calc R . .
H15C H 0.2469 0.9847 -0.1492 0.037 Uiso 1 1 calc R . .
C16 C 0.3917(3) 0.8253(2) -0.0714(2) 0.0260(6) Uani 1 1 d . . .
H16A H 0.4072 0.8420 -0.1312 0.039 Uiso 1 1 calc R . .
H16B H 0.3955 0.7546 -0.0634 0.039 Uiso 1 1 calc R . .
H16C H 0.4628 0.8556 -0.0214 0.039 Uiso 1 1 calc R . .
C17 C 0.2909(3) 0.9155(2) 0.13793(18) 0.0188(5) Uani 1 1 d . . .
C18 C 0.2120(3) 1.0123(2) 0.1229(2) 0.0288(6) Uani 1 1 d . . .
H18A H 0.1143 0.9998 0.1153 0.043 Uiso 1 1 calc R . .
H18B H 0.2239 1.0441 0.0672 0.043 Uiso 1 1 calc R . .
H18C H 0.2476 1.0545 0.1766 0.043 Uiso 1 1 calc R . .
C19 C 0.4441(3) 0.9335(2) 0.1497(2) 0.0234(6) Uani 1 1 d . . .
H19A H 0.4567 0.9634 0.0934 0.035 Uiso 1 1 calc R . .
H19B H 0.4935 0.8716 0.1609 0.035 Uiso 1 1 calc R . .
H19C H 0.4800 0.9770 0.2025 0.035 Uiso 1 1 calc R . .
C20 C 0.2713(3) 0.8696(2) 0.2267(2) 0.0251(6) Uani 1 1 d . . .
H20A H 0.3044 0.9145 0.2787 0.038 Uiso 1 1 calc R . .
H20B H 0.3233 0.8088 0.2396 0.038 Uiso 1 1 calc R . .
H20C H 0.1737 0.8562 0.2186 0.038 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 1.955(2) . ?
Ir1 N1 2.158(2) . ?
Ir1 P1 2.2239(7) . ?
Ir1 Cl1 2.3929(7) . ?
Ir1 H1M 1.1328 . ?
N1 C11 1.351(4) . ?
N1 C7 1.366(4) . ?
O1 C2 1.388(3) . ?
O1 P1 1.6672(19) . ?
P1 C13 1.866(3) . ?
P1 C17 1.867(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.399(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.401(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.466(4) . ?
C7 C8 1.392(4) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.493(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.526(4) . ?
C13 C14 1.540(4) . ?
C13 C16 1.542(4) . ?
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 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C19 1.534(4) . ?
C17 C20 1.536(4) . ?
C17 C18 1.538(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
_geom_angle_publ_flag
C1 Ir1 N1 78.82(10) . . ?
C1 Ir1 P1 81.83(8) . . ?
N1 Ir1 P1 160.61(7) . . ?
C1 Ir1 Cl1 140.23(8) . . ?
N1 Ir1 Cl1 93.32(6) . . ?
P1 Ir1 Cl1 102.49(2) . . ?
C1 Ir1 H1M 66.9 . . ?
N1 Ir1 H1M 93.8 . . ?
P1 Ir1 H1M 77.3 . . ?
Cl1 Ir1 H1M 152.8 . . ?
C11 N1 C7 119.2(3) . . ?
C11 N1 Ir1 128.4(2) . . ?
C7 N1 Ir1 112.33(19) . . ?
C2 O1 P1 114.10(17) . . ?
O1 P1 C13 103.35(11) . . ?
O1 P1 C17 99.43(11) . . ?
C13 P1 C17 111.98(12) . . ?
O1 P1 Ir1 103.85(7) . . ?
C13 P1 Ir1 116.57(9) . . ?
C17 P1 Ir1 118.32(9) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 Ir1 121.22(19) . . ?
C6 C1 Ir1 118.1(2) . . ?
C3 C2 O1 121.2(3) . . ?
C3 C2 C1 121.2(3) . . ?
O1 C2 C1 117.7(2) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 C7 114.5(2) . . ?
C5 C6 C7 126.6(3) . . ?
N1 C7 C8 121.0(3) . . ?
N1 C7 C6 114.6(2) . . ?
C8 C7 C6 124.4(3) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
N1 C11 C10 120.9(3) . . ?
N1 C11 C12 117.3(3) . . ?
C10 C11 C12 121.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C14 107.8(2) . . ?
C15 C13 C16 110.1(2) . . ?
C14 C13 C16 109.2(2) . . ?
C15 C13 P1 115.25(19) . . ?
C14 C13 P1 107.25(19) . . ?
C16 C13 P1 107.10(18) . . ?
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 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C17 C20 109.4(2) . . ?
C19 C17 C18 110.2(2) . . ?
C20 C17 C18 107.4(2) . . ?
C19 C17 P1 110.23(18) . . ?
C20 C17 P1 105.23(19) . . ?
C18 C17 P1 114.10(19) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Ir1 N1 C11 171.7(2) . . . . ?
P1 Ir1 N1 C11 167.54(17) . . . . ?
Cl1 Ir1 N1 C11 -47.7(2) . . . . ?
C1 Ir1 N1 C7 -11.58(18) . . . . ?
P1 Ir1 N1 C7 -15.7(3) . . . . ?
Cl1 Ir1 N1 C7 129.08(17) . . . . ?
C2 O1 P1 C13 134.21(19) . . . . ?
C2 O1 P1 C17 -110.36(19) . . . . ?
C2 O1 P1 Ir1 12.07(19) . . . . ?
C1 Ir1 P1 O1 -7.20(11) . . . . ?
N1 Ir1 P1 O1 -3.1(2) . . . . ?
Cl1 Ir1 P1 O1 -146.98(8) . . . . ?
C1 Ir1 P1 C13 -120.11(12) . . . . ?
N1 Ir1 P1 C13 -116.0(2) . . . . ?
Cl1 Ir1 P1 C13 100.12(10) . . . . ?
C1 Ir1 P1 C17 101.74(12) . . . . ?
N1 Ir1 P1 C17 105.8(2) . . . . ?
Cl1 Ir1 P1 C17 -38.03(10) . . . . ?
N1 Ir1 C1 C2 -176.4(2) . . . . ?
P1 Ir1 C1 C2 2.2(2) . . . . ?
Cl1 Ir1 C1 C2 101.9(2) . . . . ?
N1 Ir1 C1 C6 10.02(19) . . . . ?
P1 Ir1 C1 C6 -171.4(2) . . . . ?
Cl1 Ir1 C1 C6 -71.6(2) . . . . ?
P1 O1 C2 C3 166.6(2) . . . . ?
P1 O1 C2 C1 -11.9(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
Ir1 C1 C2 C3 -173.3(2) . . . . ?
C6 C1 C2 O1 178.6(2) . . . . ?
Ir1 C1 C2 O1 5.2(3) . . . . ?
O1 C2 C3 C4 -178.0(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
Ir1 C1 C6 C5 173.0(2) . . . . ?
C2 C1 C6 C7 179.2(2) . . . . ?
Ir1 C1 C6 C7 -7.1(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C5 C6 C7 -179.3(3) . . . . ?
C11 N1 C7 C8 8.2(4) . . . . ?
Ir1 N1 C7 C8 -168.9(2) . . . . ?
C11 N1 C7 C6 -171.8(2) . . . . ?
Ir1 N1 C7 C6 11.1(3) . . . . ?
C1 C6 C7 N1 -3.5(3) . . . . ?
C5 C6 C7 N1 176.3(3) . . . . ?
C1 C6 C7 C8 176.6(3) . . . . ?
C5 C6 C7 C8 -3.6(4) . . . . ?
N1 C7 C8 C9 -2.8(4) . . . . ?
C6 C7 C8 C9 177.1(3) . . . . ?
C7 C8 C9 C10 -2.9(5) . . . . ?
C8 C9 C10 C11 3.3(5) . . . . ?
C7 N1 C11 C10 -7.7(4) . . . . ?
Ir1 N1 C11 C10 168.8(2) . . . . ?
C7 N1 C11 C12 169.6(2) . . . . ?
Ir1 N1 C11 C12 -13.8(4) . . . . ?
C9 C10 C11 N1 2.0(5) . . . . ?
C9 C10 C11 C12 -175.2(3) . . . . ?
O1 P1 C13 C15 72.3(2) . . . . ?
C17 P1 C13 C15 -33.8(2) . . . . ?
Ir1 P1 C13 C15 -174.49(17) . . . . ?
O1 P1 C13 C14 -47.7(2) . . . . ?
C17 P1 C13 C14 -153.85(19) . . . . ?
Ir1 P1 C13 C14 65.4(2) . . . . ?
O1 P1 C13 C16 -164.83(18) . . . . ?
C17 P1 C13 C16 89.1(2) . . . . ?
Ir1 P1 C13 C16 -51.6(2) . . . . ?
O1 P1 C17 C19 -166.95(19) . . . . ?
C13 P1 C17 C19 -58.3(2) . . . . ?
Ir1 P1 C17 C19 81.6(2) . . . . ?
O1 P1 C17 C20 75.22(19) . . . . ?
C13 P1 C17 C20 -176.14(18) . . . . ?
Ir1 P1 C17 C20 -36.2(2) . . . . ?
O1 P1 C17 C18 -42.3(2) . . . . ?
C13 P1 C17 C18 66.3(2) . . . . ?
Ir1 P1 C17 C18 -153.71(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.60
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.315
_refine_diff_density_min         -1.768
_refine_diff_density_rms         0.122
_database_code_depnum_ccdc_archive 'CCDC 957717'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dm12530

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H37 Cl Ir N O P'
_chemical_formula_weight         638.19

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, z'

_cell_length_a                   15.6237(15)
_cell_length_b                   16.1007(16)
_cell_length_c                   9.9759(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2509.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    7603
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1268
_exptl_absorpt_coefficient_mu    5.509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4921
_exptl_absorpt_correction_T_max  0.7702
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24962
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         30.78
_reflns_number_total             7798
_reflns_number_gt                7063
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0099P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.016(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7798
_refine_ls_number_parameters     320
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_restrained_S_all      0.880
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.394696(8) 0.193146(8) 0.342422(13) 0.01420(3) Uani 1 1 d . . .
H1M H 0.3310 0.1772 0.4346 0.021 Uiso 1 1 d R . .
N1 N 0.30240(17) 0.17992(19) 0.1890(3) 0.0148(6) Uani 1 1 d . . .
O1 O 0.42354(17) 0.33727(16) 0.5431(3) 0.0226(6) Uani 1 1 d . . .
P1 P 0.46812(6) 0.24436(6) 0.51633(10) 0.01637(19) Uani 1 1 d . A .
Cl1 Cl 0.50046(5) 0.19375(7) 0.15746(10) 0.02549(17) Uani 1 1 d . . .
C1 C 0.34987(18) 0.3054(2) 0.3409(4) 0.0177(6) Uani 1 1 d . . .
C2 C 0.3691(2) 0.3625(2) 0.4406(4) 0.0211(8) Uani 1 1 d . . .
C3 C 0.3348(3) 0.4423(2) 0.4383(5) 0.0268(9) Uani 1 1 d . . .
H3 H 0.3496 0.4819 0.5050 0.032 Uiso 1 1 calc R . .
C4 C 0.2779(2) 0.4623(2) 0.3347(5) 0.0316(9) Uani 1 1 d . . .
H4 H 0.2546 0.5167 0.3305 0.038 Uiso 1 1 calc R . .
C5 C 0.2550(3) 0.4050(3) 0.2387(5) 0.0265(9) Uani 1 1 d . . .
H5 H 0.2153 0.4199 0.1706 0.032 Uiso 1 1 calc R . .
C6 C 0.2902(2) 0.3245(2) 0.2412(4) 0.0205(8) Uani 1 1 d . . .
C7 C 0.2655(2) 0.2540(2) 0.1551(5) 0.0201(7) Uani 1 1 d . . .
C8 C 0.2047(3) 0.2579(3) 0.0543(4) 0.0269(9) Uani 1 1 d . . .
H8 H 0.1803 0.3096 0.0291 0.032 Uiso 1 1 calc R . .
C9 C 0.1799(2) 0.1854(3) -0.0093(4) 0.0303(9) Uani 1 1 d . . .
H9 H 0.1382 0.1867 -0.0786 0.036 Uiso 1 1 calc R . .
C10 C 0.2162(2) 0.1115(3) 0.0290(4) 0.0264(9) Uani 1 1 d . . .
H10 H 0.1989 0.0614 -0.0134 0.032 Uiso 1 1 calc R . .
C11 C 0.2785(2) 0.1090(2) 0.1297(4) 0.0187(8) Uani 1 1 d . . .
C12 C 0.3238(2) 0.0278(2) 0.1631(4) 0.0213(7) Uani 1 1 d . . .
C13 C 0.3729(3) 0.0287(3) 0.2951(5) 0.0288(10) Uani 1 1 d . . .
H13A H 0.4171 0.0720 0.2919 0.043 Uiso 1 1 calc R . .
H13B H 0.4000 -0.0255 0.3093 0.043 Uiso 1 1 calc R . .
H13C H 0.3333 0.0403 0.3690 0.043 Uiso 1 1 calc R . .
C14 C 0.2579(3) -0.0429(3) 0.1755(5) 0.0291(9) Uani 1 1 d . . .
H14A H 0.2146 -0.0278 0.2423 0.044 Uiso 1 1 calc R . .
H14B H 0.2870 -0.0939 0.2035 0.044 Uiso 1 1 calc R . .
H14C H 0.2302 -0.0518 0.0886 0.044 Uiso 1 1 calc R . .
C15 C 0.3850(3) 0.0089(3) 0.0467(4) 0.0291(9) Uani 1 1 d . . .
H15A H 0.3526 0.0065 -0.0373 0.044 Uiso 1 1 calc R . .
H15B H 0.4132 -0.0446 0.0624 0.044 Uiso 1 1 calc R . .
H15C H 0.4283 0.0528 0.0408 0.044 Uiso 1 1 calc R . .
C16 C 0.5811(2) 0.2791(2) 0.4932(4) 0.0194(8) Uani 1 1 d . . .
C17 C 0.5801(3) 0.3390(3) 0.3732(4) 0.0267(9) Uani 1 1 d . . .
H17A H 0.6388 0.3566 0.3528 0.040 Uiso 1 1 calc R . .
H17B H 0.5454 0.3878 0.3952 0.040 Uiso 1 1 calc R . .
H17C H 0.5557 0.3109 0.2950 0.040 Uiso 1 1 calc R . .
C18 C 0.6189(2) 0.3285(2) 0.6118(4) 0.0254(9) Uani 1 1 d . . .
H18A H 0.6269 0.2913 0.6886 0.038 Uiso 1 1 calc R . .
H18B H 0.5796 0.3734 0.6366 0.038 Uiso 1 1 calc R . .
H18C H 0.6742 0.3521 0.5857 0.038 Uiso 1 1 calc R . .
C19 C 0.6367(2) 0.2033(3) 0.4614(5) 0.0299(9) Uani 1 1 d . . .
H19A H 0.6126 0.1736 0.3844 0.045 Uiso 1 1 calc R . .
H19B H 0.6380 0.1662 0.5393 0.045 Uiso 1 1 calc R . .
H19C H 0.6950 0.2214 0.4402 0.045 Uiso 1 1 calc R . .
C20 C 0.4502(2) 0.1920(3) 0.6827(3) 0.0234(7) Uani 1 1 d . . .
C21 C 0.3624(4) 0.2095(5) 0.7286(7) 0.0331(18) Uani 0.681(7) 1 d P A 1
H21A H 0.3495 0.1754 0.8073 0.050 Uiso 0.681(7) 1 calc PR A 1
H21B H 0.3218 0.1965 0.6566 0.050 Uiso 0.681(7) 1 calc PR A 1
H21C H 0.3575 0.2684 0.7523 0.050 Uiso 0.681(7) 1 calc PR A 1
C22 C 0.4583(4) 0.0964(4) 0.6530(7) 0.0324(15) Uani 0.681(7) 1 d P A 1
H22A H 0.5173 0.0834 0.6274 0.049 Uiso 0.681(7) 1 calc PR A 1
H22B H 0.4196 0.0814 0.5795 0.049 Uiso 0.681(7) 1 calc PR A 1
H22C H 0.4429 0.0649 0.7335 0.049 Uiso 0.681(7) 1 calc PR A 1
C23 C 0.5148(4) 0.2101(4) 0.7919(6) 0.0327(17) Uani 0.681(7) 1 d P A 1
H23A H 0.4977 0.1817 0.8745 0.049 Uiso 0.681(7) 1 calc PR A 1
H23B H 0.5172 0.2701 0.8080 0.049 Uiso 0.681(7) 1 calc PR A 1
H23C H 0.5714 0.1903 0.7640 0.049 Uiso 0.681(7) 1 calc PR A 1
C21' C 0.3597(9) 0.1524(11) 0.6914(16) 0.036(4) Uani 0.319(7) 1 d PU A 2
H21D H 0.3565 0.1047 0.6307 0.054 Uiso 0.319(7) 1 calc PR A 2
H21E H 0.3166 0.1936 0.6655 0.054 Uiso 0.319(7) 1 calc PR A 2
H21F H 0.3489 0.1340 0.7835 0.054 Uiso 0.319(7) 1 calc PR A 2
C22' C 0.5163(10) 0.1329(9) 0.7112(16) 0.034(4) Uani 0.319(7) 1 d P A 2
H22D H 0.5096 0.1123 0.8030 0.052 Uiso 0.319(7) 1 calc PR A 2
H22E H 0.5724 0.1597 0.7018 0.052 Uiso 0.319(7) 1 calc PR A 2
H22F H 0.5123 0.0864 0.6482 0.052 Uiso 0.319(7) 1 calc PR A 2
C23' C 0.4492(9) 0.2636(8) 0.8010(13) 0.024(3) Uani 0.319(7) 1 d P A 2
H23D H 0.4470 0.2367 0.8891 0.036 Uiso 0.319(7) 1 calc PR A 2
H23E H 0.3988 0.2992 0.7896 0.036 Uiso 0.319(7) 1 calc PR A 2
H23F H 0.5012 0.2974 0.7945 0.036 Uiso 0.319(7) 1 calc PR A 2
C24 C 0.0218(3) 0.9628(4) 0.1325(5) 0.0585(18) Uani 1 1 d . . .
H24 H 0.0368 0.9368 0.2148 0.070 Uiso 1 1 calc R . .
C25 C 0.0436(4) 0.9257(5) 0.0107(6) 0.0645(19) Uani 1 1 d . . .
H25 H 0.0735 0.8744 0.0096 0.077 Uiso 1 1 calc R . .
C26 C 0.0216(3) 0.9636(4) -0.1066(6) 0.064(2) Uani 1 1 d . . .
H26 H 0.0368 0.9384 -0.1895 0.077 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C1 1.939(4) . ?
Ir1 N1 2.114(3) . ?
Ir1 P1 2.2374(10) . ?
Ir1 Cl1 2.4769(9) . ?
Ir1 H1M 1.3796 . ?
N1 C11 1.339(5) . ?
N1 C7 1.367(4) . ?
O1 C2 1.391(5) . ?
O1 P1 1.672(3) . ?
P1 C16 1.866(4) . ?
P1 C20 1.882(4) . ?
C1 C2 1.387(5) . ?
C1 C6 1.397(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.401(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.474(5) . ?
C7 C8 1.386(6) . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.523(5) . ?
C12 C13 1.525(6) . ?
C12 C15 1.535(6) . ?
C12 C14 1.539(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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 C19 1.532(6) . ?
C16 C17 1.537(5) . ?
C16 C18 1.543(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22' 1.432(14) . ?
C20 C21 1.474(7) . ?
C20 C23 1.514(7) . ?
C20 C21' 1.554(15) . ?
C20 C22 1.572(7) . ?
C20 C23' 1.650(14) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21' H21D 0.9800 . ?
C21' H21E 0.9800 . ?
C21' H21F 0.9800 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 0.9800 . ?
C24 C24 1.379(13) 4_575 ?
C24 C25 1.396(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.364(9) . ?
C25 H25 0.9500 . ?
C26 C26 1.354(14) 4_575 ?
C26 H26 0.9500 . ?

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
_geom_angle_publ_flag
C1 Ir1 N1 80.90(13) . . ?
C1 Ir1 P1 81.24(11) . . ?
N1 Ir1 P1 161.52(8) . . ?
C1 Ir1 Cl1 103.38(11) . . ?
N1 Ir1 Cl1 85.18(8) . . ?
P1 Ir1 Cl1 103.54(3) . . ?
C1 Ir1 H1M 85.3 . . ?
N1 Ir1 H1M 88.4 . . ?
P1 Ir1 H1M 85.5 . . ?
Cl1 Ir1 H1M 168.2 . . ?
C11 N1 C7 121.2(3) . . ?
C11 N1 Ir1 126.6(2) . . ?
C7 N1 Ir1 112.2(2) . . ?
C2 O1 P1 113.5(2) . . ?
O1 P1 C16 98.36(15) . . ?
O1 P1 C20 101.43(17) . . ?
C16 P1 C20 112.57(17) . . ?
O1 P1 Ir1 103.90(10) . . ?
C16 P1 Ir1 119.98(13) . . ?
C20 P1 Ir1 116.25(13) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 Ir1 122.3(3) . . ?
C6 C1 Ir1 116.8(3) . . ?
C1 C2 O1 117.8(3) . . ?
C1 C2 C3 121.1(4) . . ?
O1 C2 C3 121.1(4) . . ?
C2 C3 C4 117.9(4) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 121.7(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.4(4) . . ?
C1 C6 C7 114.8(3) . . ?
C5 C6 C7 126.6(3) . . ?
N1 C7 C8 120.5(4) . . ?
N1 C7 C6 114.7(3) . . ?
C8 C7 C6 124.6(3) . . ?
C9 C8 C7 119.2(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
N1 C11 C10 119.1(4) . . ?
N1 C11 C12 120.4(3) . . ?
C10 C11 C12 120.3(3) . . ?
C11 C12 C13 114.5(3) . . ?
C11 C12 C15 107.1(3) . . ?
C13 C12 C15 109.9(3) . . ?
C11 C12 C14 110.0(3) . . ?
C13 C12 C14 105.9(4) . . ?
C15 C12 C14 109.3(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C16 C17 110.1(3) . . ?
C19 C16 C18 110.6(3) . . ?
C17 C16 C18 106.2(3) . . ?
C19 C16 P1 108.8(3) . . ?
C17 C16 P1 106.0(2) . . ?
C18 C16 P1 115.0(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22' C20 C21 137.5(7) . . ?
C22' C20 C23 60.3(7) . . ?
C21 C20 C23 111.1(4) . . ?
C22' C20 C21' 111.9(9) . . ?
C21 C20 C21' 38.1(7) . . ?
C23 C20 C21' 130.2(7) . . ?
C22' C20 C22 47.9(7) . . ?
C21 C20 C22 108.7(5) . . ?
C23 C20 C22 105.8(4) . . ?
C21' C20 C22 71.5(7) . . ?
C22' C20 C23' 109.2(9) . . ?
C21 C20 C23' 68.6(6) . . ?
C23 C20 C23' 50.0(5) . . ?
C21' C20 C23' 103.7(8) . . ?
C22 C20 C23' 145.0(6) . . ?
C22' C20 P1 111.4(6) . . ?
C21 C20 P1 109.0(4) . . ?
C23 C20 P1 116.7(3) . . ?
C21' C20 P1 111.6(6) . . ?
C22 C20 P1 105.1(3) . . ?
C23' C20 P1 108.6(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
C20 C21' H21D 109.5 . . ?
C20 C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C20 C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C20 C22' H22D 109.5 . . ?
C20 C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
C20 C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
C20 C23' H23D 109.5 . . ?
C20 C23' H23E 109.5 . . ?
H23D C23' H23E 109.5 . . ?
C20 C23' H23F 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C24 C24 C25 119.4(4) 4_575 . ?
C24 C24 H24 120.3 4_575 . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 119.7(7) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C26 C26 C25 120.8(4) 4_575 . ?
C26 C26 H26 119.6 4_575 . ?
C25 C26 H26 119.6 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Ir1 N1 C11 -172.1(3) . . . . ?
P1 Ir1 N1 C11 -157.2(2) . . . . ?
Cl1 Ir1 N1 C11 83.5(3) . . . . ?
C1 Ir1 N1 C7 6.6(3) . . . . ?
P1 Ir1 N1 C7 21.5(4) . . . . ?
Cl1 Ir1 N1 C7 -97.8(2) . . . . ?
C2 O1 P1 C16 112.1(3) . . . . ?
C2 O1 P1 C20 -132.7(3) . . . . ?
C2 O1 P1 Ir1 -11.7(3) . . . . ?
C1 Ir1 P1 O1 9.20(14) . . . . ?
N1 Ir1 P1 O1 -5.7(3) . . . . ?
Cl1 Ir1 P1 O1 110.95(11) . . . . ?
C1 Ir1 P1 C16 -99.20(18) . . . . ?
N1 Ir1 P1 C16 -114.1(3) . . . . ?
Cl1 Ir1 P1 C16 2.55(15) . . . . ?
C1 Ir1 P1 C20 119.66(18) . . . . ?
N1 Ir1 P1 C20 104.8(3) . . . . ?
Cl1 Ir1 P1 C20 -138.59(15) . . . . ?
N1 Ir1 C1 C2 168.5(3) . . . . ?
P1 Ir1 C1 C2 -6.7(3) . . . . ?
Cl1 Ir1 C1 C2 -108.7(3) . . . . ?
N1 Ir1 C1 C6 -5.5(3) . . . . ?
P1 Ir1 C1 C6 179.3(3) . . . . ?
Cl1 Ir1 C1 C6 77.3(3) . . . . ?
C6 C1 C2 O1 174.7(3) . . . . ?
Ir1 C1 C2 O1 0.9(5) . . . . ?
C6 C1 C2 C3 -5.0(5) . . . . ?
Ir1 C1 C2 C3 -178.8(3) . . . . ?
P1 O1 C2 C1 8.2(4) . . . . ?
P1 O1 C2 C3 -172.0(3) . . . . ?
C1 C2 C3 C4 2.1(6) . . . . ?
O1 C2 C3 C4 -177.6(4) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C2 C1 C6 C5 4.6(5) . . . . ?
Ir1 C1 C6 C5 178.7(3) . . . . ?
C2 C1 C6 C7 -170.5(3) . . . . ?
Ir1 C1 C6 C7 3.6(4) . . . . ?
C4 C5 C6 C1 -1.5(6) . . . . ?
C4 C5 C6 C7 173.0(4) . . . . ?
C11 N1 C7 C8 -2.6(6) . . . . ?
Ir1 N1 C7 C8 178.7(3) . . . . ?
C11 N1 C7 C6 172.3(3) . . . . ?
Ir1 N1 C7 C6 -6.4(4) . . . . ?
C1 C6 C7 N1 2.3(5) . . . . ?
C5 C6 C7 N1 -172.4(4) . . . . ?
C1 C6 C7 C8 176.9(4) . . . . ?
C5 C6 C7 C8 2.3(6) . . . . ?
N1 C7 C8 C9 1.8(6) . . . . ?
C6 C7 C8 C9 -172.6(4) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C7 N1 C11 C10 1.6(5) . . . . ?
Ir1 N1 C11 C10 -179.9(3) . . . . ?
C7 N1 C11 C12 176.6(3) . . . . ?
Ir1 N1 C11 C12 -4.9(5) . . . . ?
C9 C10 C11 N1 0.1(6) . . . . ?
C9 C10 C11 C12 -174.8(4) . . . . ?
N1 C11 C12 C13 19.5(5) . . . . ?
C10 C11 C12 C13 -165.6(4) . . . . ?
N1 C11 C12 C15 -102.7(4) . . . . ?
C10 C11 C12 C15 72.2(4) . . . . ?
N1 C11 C12 C14 138.6(4) . . . . ?
C10 C11 C12 C14 -46.5(5) . . . . ?
O1 P1 C16 C19 -178.1(3) . . . . ?
C20 P1 C16 C19 75.8(3) . . . . ?
Ir1 P1 C16 C19 -66.7(3) . . . . ?
O1 P1 C16 C17 -59.6(3) . . . . ?
C20 P1 C16 C17 -165.8(3) . . . . ?
Ir1 P1 C16 C17 51.8(3) . . . . ?
O1 P1 C16 C18 57.3(3) . . . . ?
C20 P1 C16 C18 -48.9(3) . . . . ?
Ir1 P1 C16 C18 168.7(2) . . . . ?
O1 P1 C20 C22' -150.0(7) . . . . ?
C16 P1 C20 C22' -45.9(8) . . . . ?
Ir1 P1 C20 C22' 98.1(7) . . . . ?
O1 P1 C20 C21 43.3(4) . . . . ?
C16 P1 C20 C21 147.5(4) . . . . ?
Ir1 P1 C20 C21 -68.6(4) . . . . ?
O1 P1 C20 C23 -83.5(4) . . . . ?
C16 P1 C20 C23 20.7(5) . . . . ?
Ir1 P1 C20 C23 164.6(4) . . . . ?
O1 P1 C20 C21' 84.0(7) . . . . ?
C16 P1 C20 C21' -171.8(7) . . . . ?
Ir1 P1 C20 C21' -27.9(7) . . . . ?
O1 P1 C20 C22 159.7(3) . . . . ?
C16 P1 C20 C22 -96.1(3) . . . . ?
Ir1 P1 C20 C22 47.8(3) . . . . ?
O1 P1 C20 C23' -29.7(5) . . . . ?
C16 P1 C20 C23' 74.5(6) . . . . ?
Ir1 P1 C20 C23' -141.6(5) . . . . ?
C24 C24 C25 C26 0.0(9) 4_575 . . . ?
C24 C25 C26 C26 -0.4(10) . . . 4_575 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        30.78
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.103
_database_code_depnum_ccdc_archive 'CCDC 957718'
