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

#######################################################################
#
#                 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_comp-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H29 F4 Ir N4 O2'
_chemical_formula_weight         877.88

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'
F F 0.0171 0.0103 '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)

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

_cell_length_a                   13.338(11)
_cell_length_b                   9.590(8)
_cell_length_c                   13.460(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.853(9)
_cell_angle_gamma                90.00
_cell_volume                     1713(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2751
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.02

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    3.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.378
_exptl_absorpt_correction_T_max  0.403
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12407
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_sigmaI/netI    0.1243
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5936
_reflns_number_gt                4791
_reflns_threshold_expression     >2σ(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 > 2σ(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)+(0.0982P)²+11.3409P] 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   0.04(3)
_refine_ls_number_reflns         5936
_refine_ls_number_parameters     421
_refine_ls_number_restraints     213
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0908
_refine_ls_wR_factor_ref         0.2193
_refine_ls_wR_factor_gt          0.2074
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.000
_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 0.23188(4) 0.7445(3) 0.74987(5) 0.0344(2) Uani 1 1 d DU . .
N2 N 0.2027(13) 0.8306(17) 0.8904(13) 0.038(3) Uani 1 1 d U . .
N1 N 0.3629(12) 0.8626(18) 0.7601(12) 0.036(3) Uani 1 1 d U . .
N4 N 0.3132(14) 0.5810(19) 0.8124(13) 0.042(3) Uani 1 1 d U . .
C29 C 0.1234(15) 0.7846(19) 0.9496(15) 0.040(4) Uani 1 1 d U . .
H29 H 0.1245 0.6826 0.9543 0.048 Uiso 1 1 calc R . .
C28 C 0.162(2) 0.847(3) 1.0517(18) 0.061(6) Uani 1 1 d U . .
H28A H 0.1064 0.8878 1.0832 0.074 Uiso 1 1 calc R . .
H28B H 0.1930 0.7754 1.0954 0.074 Uiso 1 1 calc R . .
C27 C 0.263(2) 0.923(3) 0.9371(17) 0.054(6) Uani 1 1 d U . .
C26 C 0.344(2) 0.989(3) 0.9086(19) 0.051(6) Uani 1 1 d U . .
H26 H 0.3681 1.0624 0.9493 0.061 Uiso 1 1 calc R . .
C25 C 0.3939(17) 0.964(2) 0.8322(17) 0.043(4) Uani 1 1 d U . .
C24 C 0.5013(16) 0.998(2) 0.7205(18) 0.047(4) Uani 1 1 d U . .
H24B H 0.5726 0.9784 0.7214 0.057 Uiso 1 1 calc R . .
H24A H 0.4849 1.0764 0.6758 0.057 Uiso 1 1 calc R . .
C23 C 0.4391(15) 0.871(2) 0.6862(16) 0.039(3) Uani 1 1 d U . .
H23 H 0.4052 0.8870 0.6190 0.046 Uiso 1 1 calc R . .
C30 C 0.0203(8) 0.8314(14) 0.9114(11) 0.040(4) Uani 1 1 d GU . .
C31 C 0.0035(10) 0.9629(13) 0.8697(13) 0.055(5) Uani 1 1 d GU . .
H31 H 0.0576 1.0222 0.8630 0.066 Uiso 1 1 calc R . .
C32 C -0.0940(12) 1.0058(14) 0.8379(14) 0.060(6) Uani 1 1 d GU . .
H32 H -0.1053 1.0938 0.8100 0.072 Uiso 1 1 calc R . .
C33 C -0.1748(9) 0.9172(19) 0.8479(15) 0.094(10) Uani 1 1 d GU . .
H33 H -0.2401 0.9459 0.8267 0.113 Uiso 1 1 calc R . .
C34 C -0.1581(9) 0.7856(18) 0.8897(14) 0.074(8) Uani 1 1 d GU . .
H34 H -0.2121 0.7263 0.8964 0.089 Uiso 1 1 calc R . .
C35 C -0.0605(10) 0.7427(14) 0.9214(12) 0.074(7) Uani 1 1 d GU . .
H35 H -0.0493 0.6547 0.9494 0.089 Uiso 1 1 calc R . .
C36 C 0.5022(8) 0.7416(14) 0.6873(9) 0.039(3) Uani 1 1 d GU . .
C37 C 0.5444(12) 0.6844(16) 0.7769(8) 0.054(6) Uani 1 1 d GU . .
H37 H 0.5330 0.7259 0.8372 0.064 Uiso 1 1 calc R . .
C38 C 0.6037(14) 0.5653(17) 0.7764(12) 0.076(7) Uani 1 1 d GU . .
H38 H 0.6319 0.5271 0.8363 0.092 Uiso 1 1 calc R . .
C39 C 0.6208(15) 0.5033(16) 0.6863(15) 0.088(9) Uani 1 1 d GU . .
H39 H 0.6605 0.4236 0.6860 0.106 Uiso 1 1 calc R . .
C40 C 0.5786(15) 0.5604(19) 0.5967(12) 0.090(8) Uani 1 1 d GU . .
H40 H 0.5901 0.5189 0.5365 0.108 Uiso 1 1 calc R . .
C41 C 0.5193(12) 0.6796(19) 0.5972(8) 0.061(6) Uani 1 1 d GU . .
H41 H 0.4911 0.7178 0.5373 0.074 Uiso 1 1 calc R . .
C12 C 0.3424(18) 0.567(2) 0.9110(16) 0.038(5) Uani 1 1 d U . .
H12 H 0.3270 0.6392 0.9529 0.046 Uiso 1 1 calc R . .
C13 C 0.392(2) 0.457(3) 0.953(2) 0.054(5) Uani 1 1 d U . .
H13 H 0.4086 0.4520 1.0217 0.065 Uiso 1 1 calc R . .
C14 C 0.416(3) 0.354(3) 0.893(2) 0.082(9) Uani 1 1 d U . .
H14 H 0.4522 0.2775 0.9188 0.098 Uiso 1 1 calc R . .
C15 C 0.385(3) 0.363(3) 0.788(2) 0.076(8) Uani 1 1 d U . .
H15 H 0.4001 0.2898 0.7469 0.091 Uiso 1 1 calc R . .
C16 C 0.3327(16) 0.481(2) 0.7458(17) 0.043(4) Uani 1 1 d U . .
C17 C 0.3058(14) 0.5132(17) 0.6434(15) 0.038(3) Uani 1 1 d DU . .
C22 C 0.2632(13) 0.6447(17) 0.6248(11) 0.035(3) Uani 1 1 d DU . .
C21 C 0.2448(13) 0.688(2) 0.5273(12) 0.039(4) Uani 1 1 d DU . .
H21 H 0.2177 0.7759 0.5137 0.046 Uiso 1 1 calc R . .
C20 C 0.2660(17) 0.602(2) 0.4487(13) 0.056(5) Uani 1 1 d DU . .
C19 C 0.3058(19) 0.470(2) 0.4679(13) 0.061(5) Uani 1 1 d DU . .
H19 H 0.3194 0.4113 0.4161 0.073 Uiso 1 1 calc R . .
C18 C 0.3245(16) 0.4289(17) 0.5658(14) 0.052(4) Uani 1 1 d DU . .
N3 N 0.1463(6) 0.8977(10) 0.6798(7) 0.043(3) Uani 1 1 d GDU . .
C11 C 0.1812(8) 1.0300(12) 0.6591(9) 0.056(5) Uani 1 1 d GDU . .
H11 H 0.2479 1.0539 0.6784 0.067 Uiso 1 1 calc R . .
C10 C 0.1165(12) 1.1265(9) 0.6094(9) 0.086(9) Uani 1 1 d GDU . .
H10 H 0.1398 1.2150 0.5955 0.103 Uiso 1 1 calc R . .
C9 C 0.0168(11) 1.0907(12) 0.5805(8) 0.083(8) Uani 1 1 d GDU . .
H9 H -0.0266 1.1553 0.5473 0.100 Uiso 1 1 calc R . .
C8 C -0.0182(6) 0.9584(13) 0.6013(7) 0.069(6) Uani 1 1 d GDU . .
H8 H -0.0849 0.9344 0.5819 0.083 Uiso 1 1 calc R . .
C7 C 0.0466(6) 0.8619(9) 0.6509(5) 0.053(4) Uani 1 1 d GDU . .
O1 O 0.2332(14) 0.951(2) 1.0329(12) 0.062(5) Uani 1 1 d U . .
O2 O 0.4767(13) 1.0307(17) 0.8187(13) 0.058(4) Uani 1 1 d U . .
F3 F 0.3592(14) 0.2982(13) 0.5801(12) 0.082(5) Uani 1 1 d DU . .
F4 F 0.2491(13) 0.652(2) 0.3548(10) 0.082(5) Uani 1 1 d DU . .
C1 C 0.1005(5) 0.6402(11) 0.7287(7) 0.057(3) Uani 1 1 d GDU . .
C2 C 0.0233(6) 0.7186(9) 0.6792(6) 0.068(3) Uani 1 1 d GDU . .
C3 C -0.0720(5) 0.6605(12) 0.6578(6) 0.065(3) Uani 1 1 d GDU . .
C4 C -0.0900(7) 0.5241(13) 0.6861(8) 0.069(3) Uani 1 1 d GDU . .
H4 H -0.1537 0.4853 0.6718 0.083 Uiso 1 1 calc R . .
C5 C -0.0127(10) 0.4457(9) 0.7356(8) 0.065(4) Uani 1 1 d GDU . .
C6 C 0.0826(9) 0.5038(10) 0.7570(8) 0.060(5) Uani 1 1 d GDU . .
H6 H 0.1343 0.4513 0.7901 0.072 Uiso 1 1 calc R . .
F2 F -0.1504(9) 0.7181(19) 0.6122(9) 0.084(5) Uani 1 1 d DU . .
F1 F -0.0266(13) 0.3125(14) 0.7647(11) 0.097(5) Uani 1 1 d DU . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C22 2.017(15) . ?
Ir1 C1 2.012(8) . ?
Ir1 N4 2.039(19) . ?
Ir1 N3 2.032(8) . ?
Ir1 N1 2.076(17) . ?
Ir1 N2 2.135(17) . ?
N2 C27 1.32(3) . ?
N2 C29 1.46(3) . ?
N1 C25 1.41(3) . ?
N1 C23 1.50(3) . ?
N4 C12 1.35(3) . ?
N4 C16 1.35(3) . ?
C29 C30 1.49(2) . ?
C29 C28 1.54(3) . ?
C28 O1 1.42(3) . ?
C27 C26 1.34(3) . ?
C27 O1 1.41(3) . ?
C26 C25 1.30(3) . ?
C25 O2 1.30(3) . ?
C24 O2 1.43(3) . ?
C24 C23 1.52(3) . ?
C23 C36 1.50(2) . ?
C30 C31 1.3900 . ?
C30 C35 1.3900 . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.3900 . ?
C36 C37 1.3900 . ?
C36 C41 1.3900 . ?
C37 C38 1.3900 . ?
C38 C39 1.3900 . ?
C39 C40 1.3900 . ?
C40 C41 1.3900 . ?
C12 C13 1.34(3) . ?
C13 C14 1.33(4) . ?
C14 C15 1.43(4) . ?
C15 C16 1.42(3) . ?
C16 C17 1.42(3) . ?
C17 C18 1.36(3) . ?
C17 C22 1.396(17) . ?
C22 C21 1.374(16) . ?
C21 C20 1.39(3) . ?
C20 F4 1.349(16) . ?
C20 C19 1.389(17) . ?
C19 C18 1.373(16) . ?
C18 F3 1.343(16) . ?
N3 C11 1.3900 . ?
N3 C7 1.3900 . ?
C11 C10 1.3900 . ?
C10 C9 1.3900 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 C2 1.468(9) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 F2 1.283(13) . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 F1 1.354(15) . ?

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
C22 Ir1 C1 84.1(6) . . ?
C22 Ir1 N4 80.4(7) . . ?
C1 Ir1 N4 95.4(6) . . ?
C22 Ir1 N3 96.3(5) . . ?
C1 Ir1 N3 81.6(4) . . ?
N4 Ir1 N3 175.8(6) . . ?
C22 Ir1 N1 94.0(7) . . ?
C1 Ir1 N1 174.8(6) . . ?
N4 Ir1 N1 89.0(7) . . ?
N3 Ir1 N1 93.8(6) . . ?
C22 Ir1 N2 174.1(7) . . ?
C1 Ir1 N2 94.7(5) . . ?
N4 Ir1 N2 94.0(7) . . ?
N3 Ir1 N2 89.2(5) . . ?
N1 Ir1 N2 87.6(6) . . ?
C27 N2 C29 112.7(17) . . ?
C27 N2 Ir1 121.8(15) . . ?
C29 N2 Ir1 125.2(12) . . ?
C25 N1 C23 104.4(16) . . ?
C25 N1 Ir1 127.6(14) . . ?
C23 N1 Ir1 127.6(12) . . ?
C12 N4 C16 121.7(19) . . ?
C12 N4 Ir1 124.8(14) . . ?
C16 N4 Ir1 113.5(15) . . ?
N2 C29 C30 114.6(16) . . ?
N2 C29 C28 100.3(16) . . ?
C30 C29 C28 113.7(18) . . ?
O1 C28 C29 106.4(18) . . ?
N2 C27 C26 131(2) . . ?
N2 C27 O1 110(2) . . ?
C26 C27 O1 119(2) . . ?
C25 C26 C27 129(2) . . ?
C26 C25 O2 122(2) . . ?
C26 C25 N1 122(2) . . ?
O2 C25 N1 115.8(19) . . ?
O2 C24 C23 106.6(17) . . ?
N1 C23 C36 111.5(15) . . ?
N1 C23 C24 103.2(17) . . ?
C36 C23 C24 111.9(16) . . ?
C31 C30 C35 120.0 . . ?
C31 C30 C29 121.2(11) . . ?
C35 C30 C29 118.7(11) . . ?
C32 C31 C30 120.0 . . ?
C31 C32 C33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C35 C34 C33 120.0 . . ?
C34 C35 C30 120.0 . . ?
C37 C36 C41 120.0 . . ?
C37 C36 C23 120.8(12) . . ?
C41 C36 C23 119.2(12) . . ?
C36 C37 C38 120.0 . . ?
C37 C38 C39 120.0 . . ?
C40 C39 C38 120.0 . . ?
C39 C40 C41 120.0 . . ?
C40 C41 C36 120.0 . . ?
C13 C12 N4 125(2) . . ?
C14 C13 C12 118(3) . . ?
C13 C14 C15 120(2) . . ?
C14 C15 C16 122(2) . . ?
N4 C16 C15 115(2) . . ?
N4 C16 C17 116.4(19) . . ?
C15 C16 C17 129(2) . . ?
C18 C17 C16 124.6(16) . . ?
C18 C17 C22 120.1(17) . . ?
C16 C17 C22 115.2(16) . . ?
C21 C22 C17 118.2(16) . . ?
C21 C22 Ir1 128.5(13) . . ?
C17 C22 Ir1 113.2(12) . . ?
C22 C21 C20 121.3(18) . . ?
F4 C20 C19 121.5(19) . . ?
F4 C20 C21 118.5(17) . . ?
C19 C20 C21 120.0(15) . . ?
C18 C19 C20 118.1(14) . . ?
F3 C18 C17 122.0(17) . . ?
F3 C18 C19 115.7(17) . . ?
C17 C18 C19 122.3(15) . . ?
C11 N3 C7 120.0 . . ?
C11 N3 Ir1 124.7(6) . . ?
C7 N3 Ir1 115.3(6) . . ?
C10 C11 N3 120.0 . . ?
C9 C10 C11 120.0 . . ?
C10 C9 C8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C8 C7 N3 120.0 . . ?
C8 C7 C2 127.6(7) . . ?
N3 C7 C2 112.4(7) . . ?
C27 O1 C28 106.8(17) . . ?
C25 O2 C24 107.6(17) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 Ir1 113.0(6) . . ?
C6 C1 Ir1 127.0(6) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 C7 117.7(7) . . ?
C3 C2 C7 122.3(7) . . ?
F2 C3 C4 112.4(11) . . ?
F2 C3 C2 127.6(11) . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 F1 117.8(12) . . ?
C4 C5 F1 122.2(12) . . ?
C5 C6 C1 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         2.995
_refine_diff_density_min         -2.598
_refine_diff_density_rms         0.285
#===END
_database_code_depnum_ccdc_archive 'CCDC 955144'
#######################################################################
#
#                 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_comp2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H23 Cl2 F4 Ir N4 O2'
_chemical_formula_weight         810.62

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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   9.9118(4)
_cell_length_b                   18.8734(9)
_cell_length_c                   15.8937(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.6410(10)
_cell_angle_gamma                90.00
_cell_volume                     2901.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    4.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32157
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         27.87
_reflns_number_total             6838
_reflns_number_gt                5206
_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)+(0.0332P)²+0.7827P] 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         6838
_refine_ls_number_parameters     391
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
Ir Ir 0.831635(12) 0.874757(7) 0.700998(8) 0.03030(5) Uani 1 1 d . . .
F1 F 0.5850(3) 1.11849(13) 0.56870(18) 0.0739(8) Uani 1 1 d . . .
F2 F 0.6249(3) 1.07711(14) 0.86175(16) 0.0731(8) Uani 1 1 d . . .
C1 C 0.7454(3) 0.97080(17) 0.7001(2) 0.0335(7) Uani 1 1 d . . .
C2 C 0.7221(4) 0.99284(19) 0.7808(2) 0.0376(8) Uani 1 1 d . . .
C3 C 0.6518(4) 1.0559(2) 0.7855(2) 0.0446(9) Uani 1 1 d . . .
C4 C 0.6046(4) 1.0992(2) 0.7159(3) 0.0498(10) Uani 1 1 d . . .
H4 H 0.5583 1.1413 0.7207 0.060 Uiso 1 1 calc R . .
C5 C 0.6300(4) 1.0765(2) 0.6389(3) 0.0466(9) Uani 1 1 d . . .
C6 C 0.6982(4) 1.0151(2) 0.6291(2) 0.0417(8) Uani 1 1 d . . .
H6 H 0.7132 1.0027 0.5753 0.050 Uiso 1 1 calc R . .
N3 N 0.8227(3) 0.88240(15) 0.82718(19) 0.0372(7) Uani 1 1 d . . .
C11 C 0.8699(4) 0.8322(2) 0.8865(2) 0.0490(10) Uani 1 1 d . . .
H11 H 0.9041 0.7903 0.8685 0.059 Uiso 1 1 calc R . .
C9 C 0.8206(6) 0.9027(3) 0.9984(3) 0.0788(16) Uani 1 1 d . . .
H9 H 0.8212 0.9099 1.0563 0.095 Uiso 1 1 calc R . .
C10 C 0.8699(5) 0.8402(3) 0.9719(3) 0.0661(13) Uani 1 1 d . . .
H10 H 0.9024 0.8043 1.0112 0.079 Uiso 1 1 calc R . .
N1 N 0.9136(3) 0.76978(16) 0.70921(19) 0.0375(7) Uani 1 1 d . . .
N2 N 0.6335(3) 0.82574(16) 0.67539(19) 0.0368(6) Uani 1 1 d . . .
O2 O 0.9184(3) 0.65082(14) 0.70066(17) 0.0498(7) Uani 1 1 d . . .
O1 O 0.4708(3) 0.74184(15) 0.6648(2) 0.0575(8) Uani 1 1 d . . .
C25 C 0.8414(4) 0.7111(2) 0.6986(2) 0.0377(8) Uani 1 1 d . . .
C27 C 0.6084(4) 0.7584(2) 0.6767(2) 0.0388(8) Uani 1 1 d . . .
C29 C 0.5035(4) 0.8649(2) 0.6653(3) 0.0565(11) Uani 1 1 d . . .
H29A H 0.4908 0.8968 0.6163 0.068 Uiso 1 1 calc R . .
H29B H 0.5010 0.8921 0.7167 0.068 Uiso 1 1 calc R . .
C26 C 0.6994(4) 0.7017(2) 0.6868(3) 0.0428(9) Uani 1 1 d D . .
H100 H 0.667(4) 0.6534(12) 0.678(2) 0.051 Uiso 1 1 d D . .
C23 C 1.0594(4) 0.7515(2) 0.7129(3) 0.0584(11) Uani 1 1 d . . .
H23A H 1.1195 0.7720 0.7635 0.070 Uiso 1 1 calc R . .
H23B H 1.0883 0.7682 0.6618 0.070 Uiso 1 1 calc R . .
C24 C 1.0618(4) 0.6722(3) 0.7173(3) 0.0629(12) Uani 1 1 d . . .
H24A H 1.1071 0.6526 0.6742 0.075 Uiso 1 1 calc R . .
H24B H 1.1104 0.6562 0.7738 0.075 Uiso 1 1 calc R . .
N4 N 0.8526(3) 0.87527(14) 0.57630(18) 0.0340(6) Uani 1 1 d . . .
C17 C 1.0664(3) 0.92827(18) 0.6393(2) 0.0359(8) Uani 1 1 d . . .
C14 C 0.8965(5) 0.8744(2) 0.4112(3) 0.0561(11) Uani 1 1 d . . .
H14 H 0.9117 0.8742 0.3555 0.067 Uiso 1 1 calc R . .
F3 F 1.2438(2) 0.96733(14) 0.57112(15) 0.0607(6) Uani 1 1 d . . .
C15 C 0.9960(4) 0.9005(2) 0.4781(2) 0.0492(10) Uani 1 1 d . . .
H15 H 1.0787 0.9177 0.4676 0.059 Uiso 1 1 calc R . .
C12 C 0.7563(4) 0.8501(2) 0.5100(2) 0.0435(9) Uani 1 1 d . . .
H12 H 0.6737 0.8330 0.5207 0.052 Uiso 1 1 calc R . .
C13 C 0.7756(5) 0.8487(2) 0.4266(3) 0.0523(10) Uani 1 1 d . . .
H13 H 0.7076 0.8307 0.3818 0.063 Uiso 1 1 calc R . .
C16 C 0.9735(4) 0.90131(19) 0.5614(2) 0.0364(8) Uani 1 1 d . . .
C18 C 1.1938(4) 0.9597(2) 0.6437(2) 0.0422(9) Uani 1 1 d . . .
F4 F 1.3071(2) 1.00121(15) 0.86691(16) 0.0684(7) Uani 1 1 d . . .
C7 C 0.7712(4) 0.9438(2) 0.8528(2) 0.0417(8) Uani 1 1 d . . .
C8 C 0.7706(5) 0.9541(3) 0.9391(3) 0.0649(13) Uani 1 1 d . . .
H8 H 0.7362 0.9961 0.9567 0.078 Uiso 1 1 calc R . .
C22 C 1.0183(3) 0.92099(18) 0.7167(2) 0.0346(7) Uani 1 1 d . . .
C21 C 1.1011(4) 0.9464(2) 0.7931(2) 0.0415(8) Uani 1 1 d . . .
H21 H 1.0719 0.9425 0.8447 0.050 Uiso 1 1 calc R . .
C20 C 1.2256(4) 0.9772(2) 0.7915(3) 0.0454(9) Uani 1 1 d . . .
C28 C 0.3949(4) 0.8077(2) 0.6507(4) 0.0713(14) Uani 1 1 d . . .
H28A H 0.3348 0.8125 0.6910 0.086 Uiso 1 1 calc R . .
H28B H 0.3392 0.8100 0.5925 0.086 Uiso 1 1 calc R . .
C19 C 1.2759(4) 0.9854(2) 0.7183(3) 0.0465(9) Uani 1 1 d . . .
H19 H 1.3605 1.0070 0.7192 0.056 Uiso 1 1 calc R . .
Cl1 Cl 0.7574(3) 0.18927(19) 0.03835(16) 0.1878(13) Uani 1 1 d . . .
Cl2 Cl 0.5218(3) 0.19902(15) 0.11177(18) 0.1754(10) Uani 1 1 d . . .
C30 C 0.5903(8) 0.1648(5) 0.0322(5) 0.138(3) Uani 1 1 d . . .
H30A H 0.5349 0.1800 -0.0230 0.165 Uiso 1 1 calc R . .
H30B H 0.5855 0.1135 0.0344 0.165 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
Ir C1 2.003(3) . ?
Ir C22 2.011(3) . ?
Ir N3 2.032(3) . ?
Ir N4 2.037(3) . ?
Ir N2 2.128(3) . ?
Ir N1 2.135(3) . ?
F1 C5 1.362(4) . ?
F2 C3 1.357(4) . ?
C1 C6 1.399(5) . ?
C1 C2 1.415(4) . ?
C2 C3 1.390(5) . ?
C2 C7 1.470(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.370(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(5) . ?
C6 H6 0.9300 . ?
N3 C11 1.346(5) . ?
N3 C7 1.363(4) . ?
C11 C10 1.365(5) . ?
C11 H11 0.9300 . ?
C9 C8 1.367(6) . ?
C9 C10 1.379(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
N1 C25 1.310(5) . ?
N1 C23 1.474(4) . ?
N2 C27 1.297(4) . ?
N2 C29 1.463(4) . ?
O2 C25 1.367(4) . ?
O2 C24 1.444(5) . ?
O1 C27 1.371(4) . ?
O1 C28 1.445(5) . ?
C25 C26 1.390(5) . ?
C27 C26 1.386(5) . ?
C29 C28 1.506(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C26 H100 0.966(19) . ?
C23 C24 1.500(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
N4 C12 1.344(5) . ?
N4 C16 1.363(4) . ?
C17 C18 1.383(5) . ?
C17 C22 1.419(4) . ?
C17 C16 1.463(5) . ?
C14 C13 1.364(6) . ?
C14 C15 1.373(6) . ?
C14 H14 0.9300 . ?
F3 C18 1.358(4) . ?
C15 C16 1.391(5) . ?
C15 H15 0.9300 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C18 C19 1.372(5) . ?
F4 C20 1.368(4) . ?
C7 C8 1.387(5) . ?
C8 H8 0.9300 . ?
C22 C21 1.393(5) . ?
C21 C20 1.369(5) . ?
C21 H21 0.9300 . ?
C20 C19 1.372(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C19 H19 0.9300 . ?
Cl1 C30 1.701(8) . ?
Cl2 C30 1.689(8) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?

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 Ir C22 89.29(13) . . ?
C1 Ir N3 80.35(13) . . ?
C22 Ir N3 94.86(12) . . ?
C1 Ir N4 97.05(12) . . ?
C22 Ir N4 80.31(12) . . ?
N3 Ir N4 174.58(11) . . ?
C1 Ir N2 91.01(12) . . ?
C22 Ir N2 176.17(12) . . ?
N3 Ir N2 88.96(11) . . ?
N4 Ir N2 95.86(11) . . ?
C1 Ir N1 175.34(12) . . ?
C22 Ir N1 93.86(12) . . ?
N3 Ir N1 95.96(11) . . ?
N4 Ir N1 86.87(11) . . ?
N2 Ir N1 86.07(11) . . ?
C6 C1 C2 117.6(3) . . ?
C6 C1 Ir 127.8(3) . . ?
C2 C1 Ir 114.4(2) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 C7 125.6(3) . . ?
C1 C2 C7 115.4(3) . . ?
F2 C3 C4 116.5(3) . . ?
F2 C3 C2 120.0(4) . . ?
C4 C3 C2 123.5(4) . . ?
C5 C4 C3 116.0(4) . . ?
C5 C4 H4 122.0 . . ?
C3 C4 H4 122.0 . . ?
F1 C5 C6 118.8(4) . . ?
F1 C5 C4 117.4(4) . . ?
C6 C5 C4 123.9(4) . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C11 N3 C7 119.0(3) . . ?
C11 N3 Ir 123.9(3) . . ?
C7 N3 Ir 117.1(2) . . ?
N3 C11 C10 122.9(4) . . ?
N3 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C25 N1 C23 108.1(3) . . ?
C25 N1 Ir 125.9(2) . . ?
C23 N1 Ir 125.2(3) . . ?
C27 N2 C29 109.2(3) . . ?
C27 N2 Ir 126.5(2) . . ?
C29 N2 Ir 123.7(2) . . ?
C25 O2 C24 107.1(3) . . ?
C27 O1 C28 107.1(3) . . ?
N1 C25 O2 114.4(3) . . ?
N1 C25 C26 129.4(3) . . ?
O2 C25 C26 116.2(3) . . ?
N2 C27 O1 114.2(3) . . ?
N2 C27 C26 129.5(3) . . ?
O1 C27 C26 116.3(3) . . ?
N2 C29 C28 103.7(3) . . ?
N2 C29 H29A 111.0 . . ?
C28 C29 H29A 111.0 . . ?
N2 C29 H29B 111.0 . . ?
C28 C29 H29B 111.0 . . ?
H29A C29 H29B 109.0 . . ?
C27 C26 C25 122.1(3) . . ?
C27 C26 H100 122(2) . . ?
C25 C26 H100 116(2) . . ?
N1 C23 C24 103.9(3) . . ?
N1 C23 H23A 111.0 . . ?
C24 C23 H23A 111.0 . . ?
N1 C23 H23B 111.0 . . ?
C24 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
O2 C24 C23 105.4(3) . . ?
O2 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
O2 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
C12 N4 C16 119.4(3) . . ?
C12 N4 Ir 123.7(2) . . ?
C16 N4 Ir 116.8(2) . . ?
C18 C17 C22 118.3(3) . . ?
C18 C17 C16 126.2(3) . . ?
C22 C17 C16 115.5(3) . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N4 C12 C13 122.4(4) . . ?
N4 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 118.5(4) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
N4 C16 C15 119.4(3) . . ?
N4 C16 C17 113.2(3) . . ?
C15 C16 C17 127.4(3) . . ?
F3 C18 C19 116.0(3) . . ?
F3 C18 C17 120.1(3) . . ?
C19 C18 C17 123.9(3) . . ?
N3 C7 C8 119.9(4) . . ?
N3 C7 C2 112.6(3) . . ?
C8 C7 C2 127.5(4) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C21 C22 C17 118.4(3) . . ?
C21 C22 Ir 127.4(3) . . ?
C17 C22 Ir 114.2(2) . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
F4 C20 C21 119.1(4) . . ?
F4 C20 C19 116.8(3) . . ?
C21 C20 C19 124.0(4) . . ?
O1 C28 C29 105.2(3) . . ?
O1 C28 H28A 110.7 . . ?
C29 C28 H28A 110.7 . . ?
O1 C28 H28B 110.7 . . ?
C29 C28 H28B 110.7 . . ?
H28A C28 H28B 108.8 . . ?
C20 C19 C18 115.9(3) . . ?
C20 C19 H19 122.1 . . ?
C18 C19 H19 122.1 . . ?
Cl2 C30 Cl1 113.5(5) . . ?
Cl2 C30 H30A 108.9 . . ?
Cl1 C30 H30A 108.9 . . ?
Cl2 C30 H30B 108.9 . . ?
Cl1 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.244
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.094
#===END
_database_code_depnum_ccdc_archive 'CCDC 692212'
