# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2010

data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Hamalainen, Jani'
_publ_contact_author_email       jani.hamalainen@helsinki.fi
loop_
_publ_author_name
J.Hamalainen
T.Hatanpilil
E.Puukilainen
L.Costelle
T.Pilvi
;
M.Ritala
;
M.Leskela

data_Ir
_database_code_depnum_ccdc_archive 'CCDC 767385'
#TrackingRef '- MeCpIrCHD.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(\h^5^-1-methylcyclopentadienyl)-(\h^2^,\h^2^-cyclohexadiene)-iridium(i)
;

_chemical_name_common            
;(eta$5!-1-methylcyclopentadienyl)-(eta$2!,eta$2!-
cyclohexadiene)-iridium(i)
;

_chemical_melting_point          309.15
_chemical_formula_moiety         'C12 H15 Ir'
_chemical_formula_sum            'C12 H15 Ir1'
_chemical_formula_weight         351.46

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'
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   P21/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                   5.8310(12)
_cell_length_b                   27.153(5)
_cell_length_c                   8.015(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 128.627(19)
_cell_angle_gamma                90.00
_cell_volume                     991.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13490
_cell_measurement_theta_min      5.01
_cell_measurement_theta_max      27.65

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .14
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    13.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .17
_exptl_absorpt_correction_T_max  .76
_exptl_absorpt_process_details   'Sadabs (sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13490
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.01
_diffrn_reflns_theta_max         27.65
_reflns_number_total             2273
_reflns_number_gt                1749
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'COLLECT (Nonius, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0348P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         2273
_refine_ls_number_parameters     122
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_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 0.63109(5) 0.132284(11) 0.80298(4) 0.01540(11) Uani 1 1 d . . .
C1 C 0.6375(16) 0.1757(3) 1.0417(11) 0.0187(16) Uani 1 1 d . . .
C2 C 0.3589(16) 0.1827(3) 0.8306(12) 0.0222(17) Uani 1 1 d . . .
H2A H 0.1711 0.1738 0.7871 0.04(3) Uiso 1 1 calc R . .
C3 C 0.4174(17) 0.2051(3) 0.7013(12) 0.030(2) Uani 1 1 d . . .
H3A H 0.2747 0.2129 0.5542 0.08(4) Uiso 1 1 calc R . .
C4 C 0.7257(17) 0.2140(3) 0.8275(12) 0.0251(18) Uani 1 1 d . . .
H4A H 0.8229 0.2295 0.7808 0.030 Uiso 1 1 calc R . .
C5 C 0.8609(15) 0.1953(3) 1.0369(11) 0.0192(16) Uani 1 1 d . . .
H5A H 1.0652 0.1957 1.1534 0.023 Uiso 1 1 calc R . .
C6 C 0.6815(18) 0.1539(3) 1.2309(12) 0.032(2) Uani 1 1 d . . .
H6A H 0.6785 0.1801 1.3135 0.049 Uiso 1 1 calc R . .
H6B H 0.8712 0.1369 1.3208 0.049 Uiso 1 1 calc R . .
H6C H 0.5238 0.1303 1.1825 0.049 Uiso 1 1 calc R . .
C7 C 0.6920(16) 0.0579(3) 0.9071(11) 0.0233(18) Uani 1 1 d . . .
H7A H 0.7840 0.0534 1.0612 0.028 Uiso 1 1 calc R . .
C12 C 0.4305(16) 0.0245(3) 0.7517(11) 0.0235(18) Uani 1 1 d . . .
H12A H 0.2939 0.0246 0.7858 0.06(3) Uiso 1 1 calc R . .
H12B H 0.4986 -0.0097 0.7646 0.05(3) Uiso 1 1 calc R . .
C11 C 0.2718(15) 0.0434(3) 0.5226(11) 0.0207(17) Uani 1 1 d . . .
H11A H 0.2641 0.0169 0.4347 0.025 Uiso 1 1 calc R . .
H11B H 0.0677 0.0526 0.4589 0.025 Uiso 1 1 calc R . .
C10 C 0.4281(14) 0.0876(3) 0.5214(10) 0.0181(16) Uani 1 1 d . . .
H10A H 0.3207 0.1058 0.3830 0.022 Uiso 1 1 calc R . .
C8 C 0.8952(16) 0.0701(3) 0.8644(12) 0.0215(17) Uani 1 1 d . . .
H8A H 1.1136 0.0695 0.9756 0.026 Uiso 1 1 calc R . .
C9 C 0.7474(16) 0.0863(3) 0.6509(11) 0.0193(16) Uani 1 1 d U . .
H9A H 0.8535 0.0989 0.5985 0.023 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.01496(17) 0.01448(18) 0.01597(16) -0.00165(13) 0.00927(14) -0.00060(13)
C1 0.029(4) 0.011(4) 0.023(4) -0.011(3) 0.020(3) -0.006(3)
C2 0.018(4) 0.011(4) 0.036(4) -0.002(3) 0.017(4) 0.004(3)
C3 0.034(5) 0.017(5) 0.022(4) 0.005(3) 0.010(4) 0.005(4)
C4 0.034(4) 0.013(5) 0.039(5) 0.000(4) 0.028(4) -0.003(4)
C5 0.017(4) 0.014(4) 0.025(4) -0.003(3) 0.012(3) -0.004(3)
C6 0.041(5) 0.036(6) 0.027(4) -0.011(4) 0.025(4) -0.011(4)
C7 0.023(4) 0.027(5) 0.012(4) 0.003(3) 0.007(3) 0.001(3)
C12 0.023(4) 0.024(5) 0.021(4) -0.001(3) 0.012(3) -0.005(3)
C11 0.017(4) 0.019(5) 0.020(4) -0.009(3) 0.008(3) -0.006(3)
C10 0.021(4) 0.019(5) 0.013(3) 0.000(3) 0.010(3) 0.001(3)
C8 0.016(4) 0.007(4) 0.030(4) -0.006(3) 0.008(3) 0.002(3)
C9 0.034(4) 0.007(4) 0.033(4) -0.006(3) 0.028(4) 0.000(3)

_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 C8 2.125(7) . ?
Ir1 C9 2.130(6) . ?
Ir1 C7 2.130(8) . ?
Ir1 C10 2.153(7) . ?
Ir1 C3 2.204(8) . ?
Ir1 C2 2.209(7) . ?
Ir1 C1 2.228(6) . ?
Ir1 C5 2.258(7) . ?
Ir1 C4 2.265(8) . ?
C1 C5 1.429(9) . ?
C1 C2 1.451(10) . ?
C1 C6 1.494(10) . ?
C2 C3 1.415(10) . ?
C2 H2A 0.9500 . ?
C3 C4 1.429(11) . ?
C3 H3A 0.9500 . ?
C4 C5 1.430(10) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.462(10) . ?
C7 C12 1.524(10) . ?
C7 H7A 1.0000 . ?
C12 C11 1.539(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 C10 1.509(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 C9 1.460(9) . ?
C10 H10A 1.0000 . ?
C8 C9 1.422(10) . ?
C8 H8A 1.0000 . ?
C9 H9A 1.0000 . ?

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
C8 Ir1 C9 39.1(3) . . ?
C8 Ir1 C7 40.2(3) . . ?
C9 Ir1 C7 68.5(3) . . ?
C8 Ir1 C10 68.9(3) . . ?
C9 Ir1 C10 39.9(3) . . ?
C7 Ir1 C10 74.0(3) . . ?
C8 Ir1 C3 163.5(3) . . ?
C9 Ir1 C3 128.5(3) . . ?
C7 Ir1 C3 156.0(3) . . ?
C10 Ir1 C3 107.7(3) . . ?
C8 Ir1 C2 158.6(3) . . ?
C9 Ir1 C2 157.8(3) . . ?
C7 Ir1 C2 120.2(3) . . ?
C10 Ir1 C2 119.7(3) . . ?
C3 Ir1 C2 37.4(3) . . ?
C8 Ir1 C1 126.9(3) . . ?
C9 Ir1 C1 164.0(3) . . ?
C7 Ir1 C1 104.8(3) . . ?
C10 Ir1 C1 154.5(3) . . ?
C3 Ir1 C1 63.0(3) . . ?
C2 Ir1 C1 38.2(3) . . ?
C8 Ir1 C5 116.1(3) . . ?
C9 Ir1 C5 133.1(3) . . ?
C7 Ir1 C5 121.7(3) . . ?
C10 Ir1 C5 161.9(3) . . ?
C3 Ir1 C5 62.2(3) . . ?
C2 Ir1 C5 62.5(3) . . ?
C1 Ir1 C5 37.2(2) . . ?
C8 Ir1 C4 131.0(3) . . ?
C9 Ir1 C4 118.4(3) . . ?
C7 Ir1 C4 157.4(3) . . ?
C10 Ir1 C4 126.0(3) . . ?
C3 Ir1 C4 37.3(3) . . ?
C2 Ir1 C4 62.3(3) . . ?
C1 Ir1 C4 62.3(3) . . ?
C5 Ir1 C4 36.9(2) . . ?
C5 C1 C2 107.2(6) . . ?
C5 C1 C6 126.4(6) . . ?
C2 C1 C6 126.4(6) . . ?
C5 C1 Ir1 72.6(4) . . ?
C2 C1 Ir1 70.2(4) . . ?
C6 C1 Ir1 124.2(5) . . ?
C3 C2 C1 107.7(6) . . ?
C3 C2 Ir1 71.1(4) . . ?
C1 C2 Ir1 71.6(4) . . ?
C3 C2 H2A 126.2 . . ?
C1 C2 H2A 126.2 . . ?
Ir1 C2 H2A 122.8 . . ?
C2 C3 C4 109.0(6) . . ?
C2 C3 Ir1 71.5(4) . . ?
C4 C3 Ir1 73.7(5) . . ?
C2 C3 H3A 125.5 . . ?
C4 C3 H3A 125.5 . . ?
Ir1 C3 H3A 121.0 . . ?
C3 C4 C5 107.4(7) . . ?
C3 C4 Ir1 69.0(4) . . ?
C5 C4 Ir1 71.3(4) . . ?
C3 C4 H4A 126.3 . . ?
C5 C4 H4A 126.3 . . ?
Ir1 C4 H4A 125.0 . . ?
C1 C5 C4 108.7(6) . . ?
C1 C5 Ir1 70.3(4) . . ?
C4 C5 Ir1 71.8(4) . . ?
C1 C5 H5A 125.7 . . ?
C4 C5 H5A 125.7 . . ?
Ir1 C5 H5A 123.8 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 119.2(6) . . ?
C8 C7 Ir1 69.7(4) . . ?
C12 C7 Ir1 113.9(5) . . ?
C8 C7 H7A 115.4 . . ?
C12 C7 H7A 115.4 . . ?
Ir1 C7 H7A 115.4 . . ?
C7 C12 C11 109.1(6) . . ?
C7 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C7 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C10 C11 C12 110.9(6) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C9 C10 C11 118.9(6) . . ?
C9 C10 Ir1 69.2(4) . . ?
C11 C10 Ir1 112.3(4) . . ?
C9 C10 H10A 116.0 . . ?
C11 C10 H10A 116.0 . . ?
Ir1 C10 H10A 116.0 . . ?
C9 C8 C7 112.4(6) . . ?
C9 C8 Ir1 70.6(4) . . ?
C7 C8 Ir1 70.1(4) . . ?
C9 C8 H8A 123.7 . . ?
C7 C8 H8A 123.7 . . ?
Ir1 C8 H8A 123.7 . . ?
C8 C9 C10 114.1(6) . . ?
C8 C9 Ir1 70.3(4) . . ?
C10 C9 Ir1 70.9(4) . . ?
C8 C9 H9A 122.8 . . ?
C10 C9 H9A 122.8 . . ?
Ir1 C9 H9A 122.8 . . ?

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 C2 C3 C4 -2.0(9) . . . . ?
C2 C3 C4 C5 1.9(9) . . . . ?
C3 C4 C5 C1 -1.1(9) . . . . ?
C4 C5 C1 C2 -0.1(8) . . . . ?
C5 C1 C2 C3 1.3(8) . . . . ?
C7 C8 C9 C10 0.4(9) . . . . ?
C8 C9 C10 C11 -47.8(9) . . . . ?
C9 C10 C11 C12 45.0(9) . . . . ?
C10 C11 C12 C7 1.9(9) . . . . ?
C11 C12 C7 C8 -48.9(9) . . . . ?
C12 C7 C8 C9 48.9(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         2.017
_refine_diff_density_min         -2.354
_refine_diff_density_rms         0.268