# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Conejero, Salvador'
_publ_contact_author_email       sconejero@iiq.csic.es

_publ_section_title              
;
A simple, general route
to 2-pyridylidene transition metal complexes
;
loop_
_publ_author_name
S.Conejero
M.Rosello-Merino
J.Diez

# Attachment '- 3b.cif'

#===============================================================================
data_3b
_database_code_depnum_ccdc_archive 'CCDC 791629'
#TrackingRef '- 3b.cif'

#===============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 Cl Ir N'
_chemical_formula_sum            'C15 H21 Cl Ir N'
_chemical_formula_weight         442.98
_chemical_compound_source        synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   10.2207(2)
_cell_length_b                   11.3062(1)
_cell_length_c                   13.6376(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.736(2)
_cell_angle_gamma                90.00
_cell_volume                     1473.84(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4481
_cell_measurement_theta_min      3.4606
_cell_measurement_theta_max      74.1332

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.037
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    19.046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_device       
;
165 mm Onyx CCD detector in \k-geometry diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 8.2640
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6182
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.63
_diffrn_reflns_theta_max         74.36
_reflns_number_total             2913
_reflns_number_gt                2571
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_solution    'SIR2004(Burla, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2007)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0389P)^2^+3.9074P] 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         2913
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_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
C1 C 0.0229(6) 0.2395(5) 0.0635(4) 0.0376(11) Uani 1 1 d . . .
C2 C 0.0193(6) 0.1686(5) -0.0201(4) 0.0383(12) Uani 1 1 d . . .
C3 C 0.1502(8) 0.1440(7) -0.0401(6) 0.0607(18) Uani 1 1 d . . .
H3A H 0.1359 0.0777 -0.0867 0.091 Uiso 1 1 calc R . .
H3B H 0.2239 0.1262 0.0249 0.091 Uiso 1 1 calc R . .
H3C H 0.1754 0.2121 -0.0715 0.091 Uiso 1 1 calc R . .
C4 C -0.1013(9) 0.1177(7) -0.0848(5) 0.064(2) Uani 1 1 d . . .
H4 H -0.0983 0.0677 -0.1381 0.077 Uiso 1 1 calc R . .
C5 C -0.2261(9) 0.1389(8) -0.0728(6) 0.070(2) Uani 1 1 d . . .
H5 H -0.3083 0.1051 -0.1179 0.084 Uiso 1 1 calc R . .
C6 C -0.2272(8) 0.2106(7) 0.0069(7) 0.063(2) Uani 1 1 d . . .
H6 H -0.3115 0.2264 0.0159 0.075 Uiso 1 1 calc R . .
C7 C -0.1119(8) 0.3310(7) 0.1637(6) 0.0626(19) Uani 1 1 d . . .
H7A H -0.1910 0.3067 0.1812 0.094 Uiso 1 1 calc R . .
H7B H -0.1210 0.4132 0.1449 0.094 Uiso 1 1 calc R . .
H7C H -0.0276 0.3192 0.2231 0.094 Uiso 1 1 calc R . .
C8 C 0.1637(7) 0.4795(6) 0.1276(5) 0.0520(15) Uani 1 1 d . . .
H8 H 0.0698 0.4607 0.1114 0.062 Uiso 1 1 calc R . .
C9 C 0.2318(7) 0.4300(6) 0.0625(5) 0.0516(15) Uani 1 1 d . . .
H9 H 0.1816 0.3789 0.0090 0.062 Uiso 1 1 calc R . .
C10 C 0.3831(8) 0.4571(8) 0.0767(6) 0.068(2) Uani 1 1 d . . .
H10A H 0.3939 0.4548 0.0089 0.082 Uiso 1 1 calc R . .
H10B H 0.4057 0.5365 0.1046 0.082 Uiso 1 1 calc R . .
C11 C 0.4838(7) 0.3714(9) 0.1491(7) 0.075(2) Uani 1 1 d . . .
H11A H 0.5720 0.4116 0.1837 0.091 Uiso 1 1 calc R . .
H11B H 0.5011 0.3077 0.1076 0.091 Uiso 1 1 calc R . .
C12 C 0.4347(6) 0.3181(6) 0.2323(6) 0.0529(16) Uani 1 1 d . . .
H12 H 0.4416 0.2364 0.2408 0.063 Uiso 1 1 calc R . .
C13 C 0.3804(7) 0.3803(6) 0.2965(5) 0.0522(15) Uani 1 1 d . . .
H13 H 0.3483 0.3382 0.3421 0.063 Uiso 1 1 calc R . .
C14 C 0.3708(10) 0.5147(7) 0.2958(7) 0.074(2) Uani 1 1 d . . .
H14A H 0.4452 0.5476 0.2755 0.089 Uiso 1 1 calc R . .
H14B H 0.3841 0.5425 0.3659 0.089 Uiso 1 1 calc R . .
C15 C 0.2292(10) 0.5589(6) 0.2198(7) 0.074(2) Uani 1 1 d . . .
H15A H 0.1655 0.5672 0.2578 0.089 Uiso 1 1 calc R . .
H15B H 0.2420 0.6367 0.1944 0.089 Uiso 1 1 calc R . .
N1 N -0.1060(6) 0.2603(6) 0.0745(5) 0.0560(14) Uani 1 1 d . . .
Cl1 Cl 0.2237(2) 0.12580(14) 0.26702(13) 0.0641(5) Uani 1 1 d . . .
Ir1 Ir 0.20945(2) 0.30005(2) 0.167564(18) 0.03773(10) Uani 1 1 d . . .

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
C1 0.039(3) 0.033(3) 0.041(3) 0.005(2) 0.013(2) -0.007(2)
C2 0.052(3) 0.035(3) 0.029(3) 0.001(2) 0.016(2) -0.002(2)
C3 0.083(5) 0.057(4) 0.055(4) -0.004(3) 0.040(4) 0.000(4)
C4 0.092(6) 0.055(4) 0.039(3) 0.005(3) 0.013(4) -0.011(4)
C5 0.064(5) 0.076(5) 0.053(4) 0.009(4) 0.000(4) -0.021(4)
C6 0.044(3) 0.067(5) 0.073(5) 0.020(4) 0.017(3) -0.003(3)
C7 0.058(4) 0.068(5) 0.079(5) -0.013(4) 0.046(4) -0.003(4)
C8 0.057(4) 0.040(3) 0.060(4) 0.012(3) 0.023(3) 0.001(3)
C9 0.049(3) 0.055(4) 0.053(4) 0.013(3) 0.022(3) -0.006(3)
C10 0.062(4) 0.080(5) 0.073(5) 0.010(4) 0.037(4) -0.020(4)
C11 0.040(3) 0.106(7) 0.089(6) -0.007(5) 0.033(4) -0.005(4)
C12 0.036(3) 0.060(4) 0.060(4) -0.005(3) 0.014(3) -0.006(3)
C13 0.049(3) 0.053(4) 0.049(3) -0.007(3) 0.009(3) -0.014(3)
C14 0.096(6) 0.050(4) 0.075(5) -0.013(4) 0.028(5) -0.017(4)
C15 0.111(7) 0.038(4) 0.084(6) 0.001(4) 0.047(5) 0.003(4)
N1 0.047(3) 0.060(3) 0.063(4) 0.005(3) 0.023(3) 0.001(3)
Cl1 0.0942(13) 0.0388(8) 0.0521(9) 0.0080(6) 0.0172(9) -0.0048(8)
Ir1 0.04013(15) 0.03393(15) 0.04110(15) 0.00275(9) 0.01681(11) 0.00009(9)

_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
C1 C2 1.383(8) . ?
C1 N1 1.398(8) . ?
C1 Ir1 2.050(5) . ?
C2 C4 1.363(9) . ?
C2 C3 1.484(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.364(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.359(12) . ?
C5 H5 0.9300 . ?
C6 N1 1.375(9) . ?
C6 H6 0.9300 . ?
C7 N1 1.474(9) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.422(9) . ?
C8 C15 1.496(11) . ?
C8 Ir1 2.110(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.520(9) . ?
C9 Ir1 2.120(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.501(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.518(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.384(10) . ?
C12 Ir1 2.163(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.523(10) . ?
C13 Ir1 2.189(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.535(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
Cl1 Ir1 2.3669(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
C2 C1 N1 115.7(5) . . ?
C2 C1 Ir1 120.7(4) . . ?
N1 C1 Ir1 123.4(4) . . ?
C4 C2 C1 122.2(6) . . ?
C4 C2 C3 117.9(6) . . ?
C1 C2 C3 119.8(6) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C5 121.2(7) . . ?
C2 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.3(7) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 N1 121.3(7) . . ?
C5 C6 H6 119.3 . . ?
N1 C6 H6 119.3 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C15 126.0(7) . . ?
C9 C8 Ir1 70.7(4) . . ?
C15 C8 Ir1 111.6(5) . . ?
C9 C8 H8 117.0 . . ?
C15 C8 H8 117.0 . . ?
Ir1 C8 H8 87.6 . . ?
C8 C9 C10 122.8(7) . . ?
C8 C9 Ir1 70.0(3) . . ?
C10 C9 Ir1 113.7(5) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
Ir1 C9 H9 86.5 . . ?
C11 C10 C9 112.5(6) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 114.6(6) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 125.8(7) . . ?
C13 C12 Ir1 72.5(4) . . ?
C11 C12 Ir1 108.6(5) . . ?
C13 C12 H12 117.1 . . ?
C11 C12 H12 117.1 . . ?
Ir1 C12 H12 88.9 . . ?
C12 C13 C14 122.8(7) . . ?
C12 C13 Ir1 70.5(4) . . ?
C14 C13 Ir1 112.2(5) . . ?
C12 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
Ir1 C13 H13 87.4 . . ?
C13 C14 C15 111.8(6) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C8 C15 C14 114.0(6) . . ?
C8 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C8 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C6 N1 C1 121.2(6) . . ?
C6 N1 C7 119.0(6) . . ?
C1 N1 C7 119.7(6) . . ?
C1 Ir1 C8 94.3(3) . . ?
C1 Ir1 C9 93.5(2) . . ?
C8 Ir1 C9 39.3(3) . . ?
C1 Ir1 C12 155.3(3) . . ?
C8 Ir1 C12 97.0(3) . . ?
C9 Ir1 C12 81.8(3) . . ?
C1 Ir1 C13 167.6(2) . . ?
C8 Ir1 C13 81.4(3) . . ?
C9 Ir1 C13 90.5(3) . . ?
C12 Ir1 C13 37.1(3) . . ?
C1 Ir1 Cl1 88.40(16) . . ?
C8 Ir1 Cl1 155.71(19) . . ?
C9 Ir1 Cl1 164.68(19) . . ?
C12 Ir1 Cl1 90.2(2) . . ?
C13 Ir1 Cl1 90.85(19) . . ?

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
N1 C1 C2 C4 -3.0(9) . . . . ?
Ir1 C1 C2 C4 173.6(5) . . . . ?
N1 C1 C2 C3 178.3(6) . . . . ?
Ir1 C1 C2 C3 -5.1(8) . . . . ?
C1 C2 C4 C5 3.0(10) . . . . ?
C3 C2 C4 C5 -178.3(7) . . . . ?
C2 C4 C5 C6 -1.2(11) . . . . ?
C4 C5 C6 N1 -0.5(11) . . . . ?
C15 C8 C9 C10 -2.7(11) . . . . ?
Ir1 C8 C9 C10 -105.9(6) . . . . ?
C15 C8 C9 Ir1 103.2(7) . . . . ?
C8 C9 C10 C11 90.7(9) . . . . ?
Ir1 C9 C10 C11 10.0(9) . . . . ?
C9 C10 C11 C12 -28.9(10) . . . . ?
C10 C11 C12 C13 -48.4(10) . . . . ?
C10 C11 C12 Ir1 33.0(9) . . . . ?
C11 C12 C13 C14 -3.7(11) . . . . ?
Ir1 C12 C13 C14 -104.3(7) . . . . ?
C11 C12 C13 Ir1 100.6(7) . . . . ?
C12 C13 C14 C15 92.2(9) . . . . ?
Ir1 C13 C14 C15 11.8(9) . . . . ?
C9 C8 C15 C14 -47.6(10) . . . . ?
Ir1 C8 C15 C14 33.7(8) . . . . ?
C13 C14 C15 C8 -29.8(10) . . . . ?
C5 C6 N1 C1 0.4(11) . . . . ?
C5 C6 N1 C7 -176.0(7) . . . . ?
C2 C1 N1 C6 1.3(9) . . . . ?
Ir1 C1 N1 C6 -175.2(5) . . . . ?
C2 C1 N1 C7 177.7(6) . . . . ?
Ir1 C1 N1 C7 1.2(8) . . . . ?
C2 C1 Ir1 C8 115.3(5) . . . . ?
N1 C1 Ir1 C8 -68.4(5) . . . . ?
C2 C1 Ir1 C9 75.9(5) . . . . ?
N1 C1 Ir1 C9 -107.7(5) . . . . ?
C2 C1 Ir1 C12 -1.8(9) . . . . ?
N1 C1 Ir1 C12 174.5(6) . . . . ?
C2 C1 Ir1 C13 -175.5(9) . . . . ?
N1 C1 Ir1 C13 0.8(14) . . . . ?
C2 C1 Ir1 Cl1 -88.9(4) . . . . ?
N1 C1 Ir1 Cl1 87.5(5) . . . . ?
C9 C8 Ir1 C1 -90.1(4) . . . . ?
C15 C8 Ir1 C1 147.7(5) . . . . ?
C15 C8 Ir1 C9 -122.1(7) . . . . ?
C9 C8 Ir1 C12 67.8(4) . . . . ?
C15 C8 Ir1 C12 -54.3(6) . . . . ?
C9 C8 Ir1 C13 101.6(4) . . . . ?
C15 C8 Ir1 C13 -20.5(5) . . . . ?
C9 C8 Ir1 Cl1 174.1(4) . . . . ?
C15 C8 Ir1 Cl1 52.0(8) . . . . ?
C8 C9 Ir1 C1 92.6(4) . . . . ?
C10 C9 Ir1 C1 -149.3(6) . . . . ?
C10 C9 Ir1 C8 118.0(7) . . . . ?
C8 C9 Ir1 C12 -111.7(4) . . . . ?
C10 C9 Ir1 C12 6.3(6) . . . . ?
C8 C9 Ir1 C13 -75.6(4) . . . . ?
C10 C9 Ir1 C13 42.4(6) . . . . ?
C8 C9 Ir1 Cl1 -170.8(6) . . . . ?
C10 C9 Ir1 Cl1 -52.8(11) . . . . ?
C13 C12 Ir1 C1 -177.8(5) . . . . ?
C11 C12 Ir1 C1 59.5(9) . . . . ?
C13 C12 Ir1 C8 65.6(4) . . . . ?
C11 C12 Ir1 C8 -57.1(6) . . . . ?
C13 C12 Ir1 C9 102.0(4) . . . . ?
C11 C12 Ir1 C9 -20.7(6) . . . . ?
C11 C12 Ir1 C13 -122.7(7) . . . . ?
C13 C12 Ir1 Cl1 -91.1(4) . . . . ?
C11 C12 Ir1 Cl1 146.2(5) . . . . ?
C12 C13 Ir1 C1 175.6(10) . . . . ?
C14 C13 Ir1 C1 -65.9(13) . . . . ?
C12 C13 Ir1 C8 -113.9(5) . . . . ?
C14 C13 Ir1 C8 4.6(6) . . . . ?
C12 C13 Ir1 C9 -75.5(4) . . . . ?
C14 C13 Ir1 C9 42.9(6) . . . . ?
C14 C13 Ir1 C12 118.4(7) . . . . ?
C12 C13 Ir1 Cl1 89.2(4) . . . . ?
C14 C13 Ir1 Cl1 -152.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        74.36
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.711
_refine_diff_density_min         -1.289
_refine_diff_density_rms         0.147
#===END

# Attachment '- 5b.cif'

#===============================================================================
data_5b
_database_code_depnum_ccdc_archive 'CCDC 791630'
#TrackingRef '- 5b.cif'

#===============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 Au Cl N'
_chemical_formula_sum            'C7 H9 Au Cl N'
_chemical_formula_weight         339.57
_chemical_compound_source        synthesis

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Au Au -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

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

_cell_length_a                   7.1822(2)
_cell_length_b                   14.0369(3)
_cell_length_c                   16.6733(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1680.93(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5618
_cell_measurement_theta_min      3.1457
_cell_measurement_theta_max      73.7276

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.093
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.019
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    35.194
_exptl_absorpt_correction_T_min  0.09864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_device       
;
165 mm Onyx CCD detector in \k-geometry diffractometer
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 8.2640
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8548
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.31
_diffrn_reflns_theta_max         73.89
_reflns_number_total             1698
_reflns_number_gt                1518
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_structure_solution    'DIRDIF-99 (Beurskens, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2007)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^ > 2\s(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^)+(0.0777P)^2^+3.5800P] 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         1698
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
C1 C 0.1066(10) 0.1655(5) 0.3242(4) 0.0224(14) Uani 1 1 d . . .
C2 C 0.0589(9) 0.2623(5) 0.3355(4) 0.0223(13) Uani 1 1 d . . .
C5 C 0.1227(9) 0.1453(5) 0.4659(4) 0.0241(15) Uani 1 1 d . . .
H5 H 0.1468 0.1045 0.5102 0.029 Uiso 1 1 calc R . .
C4 C 0.0771(11) 0.2393(5) 0.4784(4) 0.0289(15) Uani 1 1 d . . .
H4 H 0.0666 0.2639 0.5313 0.035 Uiso 1 1 calc R . .
C3 C 0.0468(10) 0.2977(5) 0.4126(4) 0.0265(14) Uani 1 1 d . . .
H3 H 0.0172 0.3630 0.4207 0.032 Uiso 1 1 calc R . .
C6 C 0.1715(11) 0.0082(5) 0.3806(4) 0.0239(14) Uani 1 1 d . . .
H6A H 0.0617 -0.0238 0.3584 0.036 Uiso 1 1 calc R . .
H6B H 0.2007 -0.0187 0.4333 0.036 Uiso 1 1 calc R . .
H6C H 0.2777 -0.0011 0.3445 0.036 Uiso 1 1 calc R . .
C7 C 0.0241(11) 0.3248(5) 0.2643(5) 0.0297(15) Uani 1 1 d . . .
H7A H -0.0347 0.3842 0.2820 0.045 Uiso 1 1 calc R . .
H7B H -0.0584 0.2918 0.2266 0.045 Uiso 1 1 calc R . .
H7C H 0.1426 0.3392 0.2379 0.045 Uiso 1 1 calc R . .
Au1 Au 0.13592(4) 0.10813(2) 0.214200(17) 0.01969(18) Uani 1 1 d . . .
Cl1 Cl 0.1660(2) 0.04358(12) 0.08815(10) 0.0264(4) Uani 1 1 d . . .
N1 N 0.1332(7) 0.1108(4) 0.3889(4) 0.0178(13) Uani 1 1 d . . .

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
C1 0.030(3) 0.019(3) 0.019(3) 0.001(3) 0.005(3) 0.000(3)
C2 0.018(3) 0.019(3) 0.030(3) 0.000(3) 0.001(3) -0.004(3)
C5 0.025(4) 0.027(4) 0.021(3) -0.007(3) -0.003(2) -0.004(3)
C4 0.038(4) 0.023(3) 0.025(3) -0.006(3) -0.002(3) -0.002(3)
C3 0.025(3) 0.023(3) 0.032(3) -0.004(3) 0.001(3) 0.002(3)
C6 0.035(3) 0.022(3) 0.015(3) -0.003(3) 0.002(3) 0.004(3)
C7 0.034(4) 0.021(3) 0.035(4) 0.002(3) -0.003(3) -0.005(3)
Au1 0.0248(3) 0.0176(2) 0.0167(2) 0.00040(9) -0.00056(9) -0.00167(9)
Cl1 0.0385(9) 0.0240(8) 0.0165(7) -0.0006(6) 0.0016(6) -0.0034(7)
N1 0.019(3) 0.017(3) 0.018(3) -0.003(2) -0.0062(19) 0.0010(18)

_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
C1 N1 1.337(9) . ?
C1 C2 1.413(9) . ?
C1 Au1 2.015(7) . ?
C2 C3 1.382(10) . ?
C2 C7 1.496(10) . ?
C5 N1 1.375(10) . ?
C5 C4 1.376(10) . ?
C5 H5 0.9500 . ?
C4 C3 1.386(10) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C6 N1 1.472(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
Au1 Cl1 2.2989(16) . ?

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
N1 C1 C2 118.7(6) . . ?
N1 C1 Au1 119.3(5) . . ?
C2 C1 Au1 122.0(5) . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 C7 121.1(6) . . ?
C1 C2 C7 119.9(6) . . ?
N1 C5 C4 119.5(7) . . ?
N1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C4 C3 118.9(7) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 Au1 Cl1 179.3(2) . . ?
C1 N1 C5 122.9(6) . . ?
C1 N1 C6 120.9(6) . . ?
C5 N1 C6 116.3(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
N1 C1 C2 C3 1.9(10) . . . . ?
Au1 C1 C2 C3 -178.0(5) . . . . ?
N1 C1 C2 C7 -178.6(6) . . . . ?
Au1 C1 C2 C7 1.5(9) . . . . ?
N1 C5 C4 C3 -1.4(11) . . . . ?
C1 C2 C3 C4 -1.3(11) . . . . ?
C7 C2 C3 C4 179.3(7) . . . . ?
C5 C4 C3 C2 1.0(11) . . . . ?
N1 C1 Au1 Cl1 135(17) . . . . ?
C2 C1 Au1 Cl1 -45(17) . . . . ?
C2 C1 N1 C5 -2.4(10) . . . . ?
Au1 C1 N1 C5 177.5(5) . . . . ?
C2 C1 N1 C6 176.1(6) . . . . ?
Au1 C1 N1 C6 -4.0(8) . . . . ?
C4 C5 N1 C1 2.2(10) . . . . ?
C4 C5 N1 C6 -176.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        73.89
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.455
_refine_diff_density_min         -1.837
_refine_diff_density_rms         0.310
#===END