# Electronic Supplementary Material (ESI) for ChemComm.
# 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
#  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_publication_text

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            '[IrCl(COD)(IMesBr)]'
_chemical_formula_moiety         'C29 H34 Br2 Cl Ir N2'
_chemical_formula_sum            'C29 H34 Br2 Cl Ir N2'
_chemical_compound_source        toluene
_chemical_melting_point          '502 (dec.)'

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         798.05

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   12.9409(3)
_cell_length_b                   11.8975(3)
_cell_length_c                   19.1295(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.4460(10)
_cell_angle_gamma                90.00
_cell_volume                     2777.25(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    7.802
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3044
_exptl_absorpt_correction_T_max  0.5092
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Apex'
_diffrn_measurement_method       'psi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31562
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         30.50
_reflns_number_total             7468
_reflns_number_gt                6201
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker AXS Collect Software'
_computing_cell_refinement       'Bruker Scalepack'
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2010'

_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)+(0.0071P)²+2.6575P] 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         7468
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0494
_refine_ls_wR_factor_gt          0.0458
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.315918(8) 0.304723(9) 0.180672(6) 0.01540(4) Uani 1 1 d . . .
Br1 Br -0.10448(2) 0.23483(3) -0.059820(17) 0.02756(7) Uani 1 1 d . . .
Br2 Br 0.11256(2) 0.22132(3) -0.145347(16) 0.02446(7) Uani 1 1 d . . .
Cl1 Cl 0.26408(6) 0.13037(6) 0.21991(4) 0.02283(15) Uani 1 1 d . . .
N1 N 0.09645(18) 0.26914(19) 0.05903(12) 0.0161(5) Uani 1 1 d . . .
N2 N 0.22374(18) 0.26470(18) 0.00946(12) 0.0144(4) Uani 1 1 d . . .
C1 C 0.2078(2) 0.2790(2) 0.07643(15) 0.0143(5) Uani 1 1 d . . .
C2 C 0.0458(2) 0.2488(2) -0.01602(16) 0.0176(6) Uani 1 1 d . . .
C3 C 0.1248(2) 0.2450(2) -0.04707(15) 0.0167(6) Uani 1 1 d . . .
C4 C 0.0342(2) 0.2731(2) 0.10926(15) 0.0173(6) Uani 1 1 d . . .
C5 C 0.0098(2) 0.3775(3) 0.13343(16) 0.0212(6) Uani 1 1 d . . .
C6 C -0.0597(2) 0.3787(3) 0.17558(17) 0.0288(7) Uani 1 1 d . . .
H6 H -0.0758 0.4483 0.1941 0.035 Uiso 1 1 calc R . .
C7 C -0.1060(2) 0.2814(3) 0.19121(17) 0.0315(8) Uani 1 1 d . . .
C8 C -0.0788(3) 0.1795(3) 0.16701(17) 0.0303(8) Uani 1 1 d . . .
H8 H -0.1086 0.1123 0.1793 0.036 Uiso 1 1 calc R . .
C9 C -0.0093(2) 0.1727(3) 0.12536(17) 0.0238(6) Uani 1 1 d . . .
C10 C 0.0525(3) 0.4862(3) 0.1141(2) 0.0316(7) Uani 1 1 d . . .
H10A H 0.0004 0.5466 0.1126 0.047 Uiso 1 1 calc R . .
H10B H 0.0617 0.4793 0.0655 0.047 Uiso 1 1 calc R . .
H10C H 0.1233 0.5036 0.1516 0.047 Uiso 1 1 calc R . .
C11 C -0.1858(3) 0.2856(4) 0.2335(2) 0.0501(11) Uani 1 1 d . . .
H11A H -0.1914 0.3629 0.2495 0.075 Uiso 1 1 calc R . .
H11B H -0.1597 0.2366 0.2771 0.075 Uiso 1 1 calc R . .
H11C H -0.2579 0.2600 0.2014 0.075 Uiso 1 1 calc R . .
C12 C 0.0158(3) 0.0596(3) 0.0987(2) 0.0337(8) Uani 1 1 d . . .
H12A H 0.0232 0.0032 0.1374 0.051 Uiso 1 1 calc R . .
H12B H 0.0844 0.0643 0.0877 0.051 Uiso 1 1 calc R . .
H12C H -0.0440 0.0380 0.0538 0.051 Uiso 1 1 calc R . .
C13 C 0.3284(2) 0.2615(2) -0.00256(15) 0.0154(5) Uani 1 1 d . . .
C14 C 0.3939(2) 0.1666(2) 0.02144(15) 0.0176(6) Uani 1 1 d . . .
C15 C 0.4973(2) 0.1669(2) 0.01382(16) 0.0197(6) Uani 1 1 d . . .
H15 H 0.5442 0.1042 0.0312 0.024 Uiso 1 1 calc R . .
C16 C 0.5336(2) 0.2566(2) -0.01855(16) 0.0206(6) Uani 1 1 d . . .
C17 C 0.4634(2) 0.3472(2) -0.04445(16) 0.0200(6) Uani 1 1 d . . .
H17 H 0.4867 0.4078 -0.0679 0.024 Uiso 1 1 calc R . .
C18 C 0.3601(2) 0.3520(2) -0.03707(15) 0.0169(5) Uani 1 1 d . . .
C19 C 0.3544(3) 0.0670(2) 0.05404(18) 0.0269(7) Uani 1 1 d . . .
H19A H 0.4100 0.0075 0.0652 0.040 Uiso 1 1 calc R . .
H19B H 0.2859 0.0389 0.0184 0.040 Uiso 1 1 calc R . .
H19C H 0.3417 0.0897 0.0997 0.040 Uiso 1 1 calc R . .
C20 C 0.6458(2) 0.2550(3) -0.02586(19) 0.0283(7) Uani 1 1 d . . .
H20A H 0.7011 0.2448 0.0232 0.042 Uiso 1 1 calc R . .
H20B H 0.6588 0.3262 -0.0473 0.042 Uiso 1 1 calc R . .
H20C H 0.6504 0.1928 -0.0583 0.042 Uiso 1 1 calc R . .
C21 C 0.2883(2) 0.4531(2) -0.06471(18) 0.0257(7) Uani 1 1 d . . .
H21A H 0.3341 0.5184 -0.0653 0.039 Uiso 1 1 calc R . .
H21B H 0.2458 0.4681 -0.0319 0.039 Uiso 1 1 calc R . .
H21C H 0.2383 0.4386 -0.1150 0.039 Uiso 1 1 calc R . .
C22 C 0.4190(2) 0.4128(3) 0.14608(16) 0.0233(6) Uani 1 1 d . . .
H22 H 0.3935 0.3757 0.0995 0.028 Uiso 1 1 calc R . .
C23 C 0.3423(3) 0.4789(3) 0.16534(19) 0.0288(7) Uani 1 1 d . . .
H23 H 0.2689 0.4810 0.1323 0.035 Uiso 1 1 calc R . .
C24 C 0.3715(3) 0.5473(3) 0.2369(2) 0.0406(9) Uani 1 1 d . . .
H24A H 0.4502 0.5675 0.2529 0.049 Uiso 1 1 calc R . .
H24B H 0.3285 0.6178 0.2273 0.049 Uiso 1 1 calc R . .
C25 C 0.3484(3) 0.4822(3) 0.2990(2) 0.0399(9) Uani 1 1 d . . .
H25A H 0.3953 0.5123 0.3474 0.048 Uiso 1 1 calc R . .
H25B H 0.2710 0.4940 0.2952 0.048 Uiso 1 1 calc R . .
C26 C 0.3695(2) 0.3580(3) 0.29611(16) 0.0271(7) Uani 1 1 d . . .
H26 H 0.3166 0.3085 0.3037 0.033 Uiso 1 1 calc R . .
C27 C 0.4587(2) 0.3095(3) 0.28351(16) 0.0254(7) Uani 1 1 d . . .
H27 H 0.4601 0.2298 0.2810 0.030 Uiso 1 1 calc R . .
C28 C 0.5541(2) 0.3721(3) 0.27340(17) 0.0296(7) Uani 1 1 d . . .
H28A H 0.6218 0.3274 0.2953 0.036 Uiso 1 1 calc R . .
H28B H 0.5637 0.4444 0.3004 0.036 Uiso 1 1 calc R . .
C29 C 0.5382(3) 0.3949(3) 0.19234(17) 0.0294(7) Uani 1 1 d . . .
H29A H 0.5807 0.4625 0.1887 0.035 Uiso 1 1 calc R . .
H29B H 0.5675 0.3306 0.1719 0.035 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 2.042(3) . ?
Ir1 C22 2.111(3) . ?
Ir1 C23 2.136(3) . ?
Ir1 C26 2.177(3) . ?
Ir1 C27 2.206(3) . ?
Ir1 Cl1 2.3773(7) . ?
Br1 C2 1.852(3) . ?
Br2 C3 1.855(3) . ?
N1 C1 1.372(3) . ?
N1 C2 1.387(3) . ?
N1 C4 1.446(3) . ?
N2 C1 1.374(3) . ?
N2 C3 1.394(3) . ?
N2 C13 1.448(3) . ?
C2 C3 1.342(4) . ?
C4 C5 1.398(4) . ?
C4 C9 1.398(4) . ?
C5 C6 1.394(4) . ?
C5 C10 1.500(4) . ?
C6 C7 1.380(5) . ?
C7 C8 1.385(5) . ?
C7 C11 1.510(4) . ?
C8 C9 1.389(4) . ?
C9 C12 1.511(4) . ?
C13 C18 1.394(4) . ?
C13 C14 1.395(4) . ?
C14 C15 1.393(4) . ?
C14 C19 1.505(4) . ?
C15 C16 1.392(4) . ?
C16 C17 1.390(4) . ?
C16 C20 1.504(4) . ?
C17 C18 1.392(4) . ?
C18 C21 1.503(4) . ?
C22 C23 1.407(4) . ?
C22 C29 1.517(4) . ?
C23 C24 1.528(5) . ?
C24 C25 1.528(5) . ?
C25 C26 1.507(5) . ?
C26 C27 1.381(4) . ?
C27 C28 1.508(4) . ?
C28 C29 1.519(4) . ?

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 C22 94.82(11) . . ?
C1 Ir1 C23 95.76(11) . . ?
C22 Ir1 C23 38.70(12) . . ?
C1 Ir1 C26 156.59(11) . . ?
C22 Ir1 C26 96.86(12) . . ?
C23 Ir1 C26 81.10(13) . . ?
C1 Ir1 C27 166.58(11) . . ?
C22 Ir1 C27 80.49(11) . . ?
C23 Ir1 C27 88.42(12) . . ?
C26 Ir1 C27 36.73(11) . . ?
C1 Ir1 Cl1 90.22(7) . . ?
C22 Ir1 Cl1 154.75(9) . . ?
C23 Ir1 Cl1 164.71(9) . . ?
C26 Ir1 Cl1 87.81(9) . . ?
C27 Ir1 Cl1 88.95(9) . . ?
C1 N1 C2 111.2(2) . . ?
C1 N1 C4 127.5(2) . . ?
C2 N1 C4 121.2(2) . . ?
C1 N2 C3 111.1(2) . . ?
C1 N2 C13 126.1(2) . . ?
C3 N2 C13 122.6(2) . . ?
N1 C1 N2 103.6(2) . . ?
N1 C1 Ir1 124.91(19) . . ?
N2 C1 Ir1 131.5(2) . . ?
C3 C2 N1 107.3(2) . . ?
C3 C2 Br1 129.5(2) . . ?
N1 C2 Br1 123.16(19) . . ?
C2 C3 N2 106.8(2) . . ?
C2 C3 Br2 129.3(2) . . ?
N2 C3 Br2 123.93(19) . . ?
C5 C4 C9 122.4(3) . . ?
C5 C4 N1 119.1(2) . . ?
C9 C4 N1 118.2(2) . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 C10 119.7(3) . . ?
C4 C5 C10 122.8(3) . . ?
C7 C6 C5 121.8(3) . . ?
C6 C7 C8 119.0(3) . . ?
C6 C7 C11 120.8(3) . . ?
C8 C7 C11 120.2(3) . . ?
C7 C8 C9 121.9(3) . . ?
C8 C9 C4 117.5(3) . . ?
C8 C9 C12 119.9(3) . . ?
C4 C9 C12 122.7(3) . . ?
C18 C13 C14 122.6(2) . . ?
C18 C13 N2 119.5(2) . . ?
C14 C13 N2 117.9(2) . . ?
C15 C14 C13 117.6(2) . . ?
C15 C14 C19 121.1(3) . . ?
C13 C14 C19 121.4(3) . . ?
C16 C15 C14 121.8(3) . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 C20 120.7(3) . . ?
C17 C16 C20 120.9(3) . . ?
C18 C17 C16 122.1(3) . . ?
C17 C18 C13 117.4(2) . . ?
C17 C18 C21 119.9(2) . . ?
C13 C18 C21 122.7(2) . . ?
C23 C22 C29 126.5(3) . . ?
C23 C22 Ir1 71.60(17) . . ?
C29 C22 Ir1 111.0(2) . . ?
C22 C23 C24 123.1(3) . . ?
C22 C23 Ir1 69.70(17) . . ?
C24 C23 Ir1 113.4(2) . . ?
C25 C24 C23 111.9(3) . . ?
C26 C25 C24 112.6(3) . . ?
C27 C26 C25 126.0(3) . . ?
C27 C26 Ir1 72.78(17) . . ?
C25 C26 Ir1 108.8(2) . . ?
C26 C27 C28 125.7(3) . . ?
C26 C27 Ir1 70.48(17) . . ?
C28 C27 Ir1 112.1(2) . . ?
C27 C28 C29 112.4(2) . . ?
C22 C29 C28 112.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.121

_database_code_depnum_ccdc_archive 'CCDC 831264'
#######################################################################
#
#                 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_publication_text

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            '[IrCl(COD)(IPrBr)].2C7H8'
_chemical_formula_moiety         'C35 H48 Br2 Cl Ir N2.2C7H8'
_chemical_formula_sum            'C49 H62 Br2 Cl Ir N2'
_chemical_compound_source        toluene
_chemical_melting_point          '465 (dec.)'

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark yellow'

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         1066.48

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   10.6872(13)
_cell_length_b                   21.9371(16)
_cell_length_c                   19.3647(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.668(3)
_cell_angle_gamma                90.00
_cell_volume                     4475.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2136
_exptl_absorpt_coefficient_mu    4.864
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4429
_exptl_absorpt_correction_T_max  0.6419
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Apex'
_diffrn_measurement_method       'psi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33217
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_sigmaI/netI    0.1065
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         29.93
_reflns_number_total             10597
_reflns_number_gt                6664
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker AXS Collect Software'
_computing_cell_refinement       'Bruker Scalepack'
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2010'

_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)+(0.0000P)²+74.4575P] 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         10597
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.39256(4) 0.397094(17) 0.278532(17) 0.01864(10) Uani 1 1 d . . .
Br1 Br 0.03764(10) 0.40109(5) 0.01032(4) 0.0268(2) Uani 1 1 d . . .
Br2 Br 0.09264(11) 0.24198(4) 0.05974(5) 0.0280(2) Uani 1 1 d . . .
Cl1 Cl 0.5429(3) 0.37528(12) 0.20556(12) 0.0266(6) Uani 1 1 d . . .
N1 N 0.1889(7) 0.4043(3) 0.1476(3) 0.0155(16) Uani 1 1 d . . .
N2 N 0.2269(8) 0.3097(3) 0.1758(3) 0.0167(17) Uani 1 1 d . . .
C1 C 0.2555(9) 0.3681(4) 0.1995(4) 0.0130(18) Uani 1 1 d . . .
C2 C 0.1263(10) 0.3696(4) 0.0925(4) 0.019(2) Uani 1 1 d . . .
C3 C 0.1493(10) 0.3108(4) 0.1099(4) 0.019(2) Uani 1 1 d . . .
C4 C 0.1657(9) 0.4691(4) 0.1565(4) 0.0166(19) Uani 1 1 d . . .
C5 C 0.2551(10) 0.5111(4) 0.1403(5) 0.021(2) Uani 1 1 d . . .
C6 C 0.2301(11) 0.5722(5) 0.1512(6) 0.032(3) Uani 1 1 d . . .
H6 H 0.2886 0.6022 0.1411 0.038 Uiso 1 1 calc R . .
C7 C 0.1230(13) 0.5903(5) 0.1762(6) 0.040(3) Uani 1 1 d . . .
H7 H 0.1091 0.6323 0.1840 0.048 Uiso 1 1 calc R . .
C8 C 0.0358(11) 0.5478(5) 0.1898(5) 0.030(2) Uani 1 1 d . . .
H8 H -0.0387 0.5610 0.2060 0.036 Uiso 1 1 calc R . .
C9 C 0.0545(10) 0.4856(4) 0.1802(5) 0.022(2) Uani 1 1 d . . .
C10 C 0.3684(10) 0.4930(5) 0.1074(5) 0.023(2) Uani 1 1 d . . .
H10 H 0.3834 0.4484 0.1151 0.028 Uiso 1 1 calc R . .
C11 C 0.4890(11) 0.5269(5) 0.1394(5) 0.031(2) Uani 1 1 d . . .
H11A H 0.4823 0.5697 0.1247 0.046 Uiso 1 1 calc R . .
H11B H 0.5624 0.5082 0.1234 0.046 Uiso 1 1 calc R . .
H11C H 0.4998 0.5246 0.1906 0.046 Uiso 1 1 calc R . .
C12 C 0.3351(13) 0.5045(6) 0.0285(5) 0.044(3) Uani 1 1 d . . .
H12A H 0.2580 0.4818 0.0095 0.067 Uiso 1 1 calc R . .
H12B H 0.4053 0.4907 0.0057 0.067 Uiso 1 1 calc R . .
H12C H 0.3207 0.5481 0.0199 0.067 Uiso 1 1 calc R . .
C13 C -0.0477(10) 0.4412(5) 0.1934(5) 0.022(2) Uani 1 1 d . . .
H13 H -0.0162 0.3992 0.1857 0.027 Uiso 1 1 calc R . .
C14 C -0.0761(13) 0.4435(6) 0.2676(5) 0.044(3) Uani 1 1 d . . .
H14A H 0.0018 0.4353 0.3008 0.066 Uiso 1 1 calc R . .
H14B H -0.1400 0.4127 0.2731 0.066 Uiso 1 1 calc R . .
H14C H -0.1084 0.4840 0.2767 0.066 Uiso 1 1 calc R . .
C15 C -0.1716(11) 0.4501(6) 0.1419(6) 0.040(3) Uani 1 1 d . . .
H15A H -0.2306 0.4170 0.1478 0.060 Uiso 1 1 calc R . .
H15B H -0.1539 0.4496 0.0939 0.060 Uiso 1 1 calc R . .
H15C H -0.2097 0.4892 0.1511 0.060 Uiso 1 1 calc R . .
C16 C 0.2497(10) 0.2534(4) 0.2163(4) 0.019(2) Uani 1 1 d . . .
C17 C 0.1613(10) 0.2384(4) 0.2602(5) 0.022(2) Uani 1 1 d . . .
C18 C 0.1780(11) 0.1819(5) 0.2934(5) 0.030(3) Uani 1 1 d . . .
H18 H 0.1214 0.1699 0.3238 0.036 Uiso 1 1 calc R . .
C19 C 0.2737(11) 0.1432(5) 0.2832(5) 0.031(3) Uani 1 1 d . . .
H19 H 0.2823 0.1049 0.3064 0.037 Uiso 1 1 calc R . .
C20 C 0.3574(11) 0.1591(4) 0.2399(5) 0.028(3) Uani 1 1 d . . .
H20 H 0.4225 0.1313 0.2331 0.034 Uiso 1 1 calc R . .
C21 C 0.3489(10) 0.2150(4) 0.2056(4) 0.022(2) Uani 1 1 d . . .
C22 C 0.0501(10) 0.2792(4) 0.2698(5) 0.025(2) Uani 1 1 d . . .
H22 H 0.0726 0.3220 0.2593 0.030 Uiso 1 1 calc R . .
C23 C 0.0251(14) 0.2771(5) 0.3455(6) 0.044(3) Uani 1 1 d . . .
H23A H -0.0123 0.2376 0.3542 0.066 Uiso 1 1 calc R . .
H23B H -0.0338 0.3098 0.3527 0.066 Uiso 1 1 calc R . .
H23C H 0.1052 0.2824 0.3778 0.066 Uiso 1 1 calc R . .
C24 C -0.0698(12) 0.2616(5) 0.2187(6) 0.039(3) Uani 1 1 d . . .
H24A H -0.0535 0.2649 0.1706 0.059 Uiso 1 1 calc R . .
H24B H -0.1392 0.2891 0.2251 0.059 Uiso 1 1 calc R . .
H24C H -0.0934 0.2196 0.2278 0.059 Uiso 1 1 calc R . .
C25 C 0.4454(10) 0.2301(5) 0.1581(5) 0.025(2) Uani 1 1 d . . .
H25 H 0.4316 0.2732 0.1418 0.029 Uiso 1 1 calc R . .
C26 C 0.5811(12) 0.2241(5) 0.1974(5) 0.036(3) Uani 1 1 d . . .
H26A H 0.6408 0.2296 0.1646 0.055 Uiso 1 1 calc R . .
H26B H 0.5929 0.1835 0.2187 0.055 Uiso 1 1 calc R . .
H26C H 0.5967 0.2552 0.2341 0.055 Uiso 1 1 calc R . .
C27 C 0.4279(11) 0.1884(5) 0.0939(5) 0.033(3) Uani 1 1 d . . .
H27A H 0.4495 0.1464 0.1087 0.049 Uiso 1 1 calc R . .
H27B H 0.4835 0.2019 0.0615 0.049 Uiso 1 1 calc R . .
H27C H 0.3393 0.1900 0.0703 0.049 Uiso 1 1 calc R . .
C28 C 0.5440(10) 0.3964(6) 0.3705(5) 0.031(2) Uani 1 1 d . . .
H28 H 0.5838 0.3641 0.3497 0.037 Uiso 1 1 calc R . .
C29 C 0.5379(11) 0.4535(5) 0.3383(5) 0.034(3) Uani 1 1 d . . .
H29 H 0.5744 0.4572 0.2970 0.040 Uiso 1 1 calc R . .
C30 C 0.4784(15) 0.5099(6) 0.3635(6) 0.051(4) Uani 1 1 d . . .
H30A H 0.5342 0.5256 0.4058 0.062 Uiso 1 1 calc R . .
H30B H 0.4726 0.5416 0.3268 0.062 Uiso 1 1 calc R . .
C31 C 0.3496(16) 0.4987(6) 0.3804(7) 0.057(4) Uani 1 1 d . . .
H31A H 0.3008 0.5372 0.3745 0.068 Uiso 1 1 calc R . .
H31B H 0.3581 0.4865 0.4302 0.068 Uiso 1 1 calc R . .
C32 C 0.2753(11) 0.4496(5) 0.3351(5) 0.028(2) Uani 1 1 d . . .
H32 H 0.2267 0.4608 0.2913 0.033 Uiso 1 1 calc R . .
C33 C 0.2767(11) 0.3863(5) 0.3569(5) 0.033(3) Uani 1 1 d . . .
H33 H 0.2251 0.3582 0.3276 0.040 Uiso 1 1 calc R . .
C34 C 0.3550(13) 0.3626(6) 0.4232(5) 0.045(3) Uani 1 1 d . . .
H34A H 0.3142 0.3753 0.4631 0.054 Uiso 1 1 calc R . .
H34B H 0.3535 0.3175 0.4216 0.054 Uiso 1 1 calc R . .
C35 C 0.4901(13) 0.3829(6) 0.4371(5) 0.047(4) Uani 1 1 d . . .
H35A H 0.5422 0.3508 0.4640 0.056 Uiso 1 1 calc R . .
H35B H 0.4968 0.4201 0.4664 0.056 Uiso 1 1 calc R . .
C36 C 0.4926(11) 0.6868(5) 0.0279(5) 0.030(2) Uani 1 1 d . . .
C37 C 0.4662(13) 0.7142(5) 0.0885(5) 0.036(3) Uani 1 1 d . . .
H37 H 0.5335 0.7226 0.1260 0.043 Uiso 1 1 calc R . .
C38 C 0.3426(13) 0.7293(5) 0.0949(6) 0.038(3) Uani 1 1 d . . .
H38 H 0.3268 0.7476 0.1371 0.046 Uiso 1 1 calc R . .
C39 C 0.2425(12) 0.7186(5) 0.0420(6) 0.036(3) Uani 1 1 d . . .
H39 H 0.1583 0.7291 0.0470 0.043 Uiso 1 1 calc R . .
C40 C 0.2681(12) 0.6920(5) -0.0191(6) 0.035(3) Uani 1 1 d . . .
H40 H 0.2007 0.6850 -0.0570 0.042 Uiso 1 1 calc R . .
C41 C 0.3900(12) 0.6757(5) -0.0256(5) 0.034(3) Uani 1 1 d . . .
H41 H 0.4047 0.6564 -0.0674 0.041 Uiso 1 1 calc R . .
C42 C 0.6242(14) 0.6698(6) 0.0208(7) 0.052(4) Uani 1 1 d . . .
H42A H 0.6807 0.7045 0.0338 0.078 Uiso 1 1 calc R . .
H42B H 0.6266 0.6582 -0.0278 0.078 Uiso 1 1 calc R . .
H42C H 0.6520 0.6352 0.0517 0.078 Uiso 1 1 calc R . .
C43 C -0.067(2) 0.5748(9) 0.4403(14) 0.109(10) Uani 1 1 d . . .
C44 C -0.0066(19) 0.5938(7) 0.3848(8) 0.066(5) Uani 1 1 d . . .
H44 H -0.0393 0.5894 0.3363 0.080 Uiso 1 1 calc R . .
C45 C 0.106(2) 0.6196(8) 0.4122(17) 0.145(13) Uani 1 1 d . . .
H45 H 0.1379 0.6324 0.3716 0.174 Uiso 1 1 calc R . .
C46 C 0.183(2) 0.6343(10) 0.455(2) 0.21(2) Uani 1 1 d . . .
H46 H 0.2650 0.6518 0.4571 0.252 Uiso 1 1 calc R . .
C47 C 0.094(4) 0.6124(14) 0.5176(13) 0.147(17) Uani 1 1 d . . .
H47 H 0.1303 0.6214 0.5647 0.176 Uiso 1 1 calc R . .
C48 C -0.014(3) 0.5861(11) 0.5100(11) 0.115(12) Uani 1 1 d . . .
H48 H -0.0550 0.5751 0.5482 0.138 Uiso 1 1 calc R . .
C49 C -0.180(2) 0.5490(10) 0.4262(16) 0.159(13) Uani 1 1 d . . .
H49A H -0.2391 0.5763 0.3966 0.238 Uiso 1 1 calc R . .
H49B H -0.2122 0.5413 0.4700 0.238 Uiso 1 1 calc R . .
H49C H -0.1740 0.5104 0.4016 0.238 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 2.035(8) . ?
Ir1 C33 2.127(11) . ?
Ir1 C32 2.135(10) . ?
Ir1 C29 2.164(10) . ?
Ir1 C28 2.196(9) . ?
Ir1 Cl1 2.360(3) . ?
Br1 C2 1.843(9) . ?
Br2 C3 1.841(9) . ?
N1 C1 1.381(10) . ?
N1 C2 1.388(11) . ?
N1 C4 1.457(11) . ?
N2 C1 1.377(11) . ?
N2 C3 1.401(11) . ?
N2 C16 1.462(11) . ?
C2 C3 1.347(12) . ?
C4 C9 1.393(14) . ?
C4 C5 1.400(13) . ?
C5 C6 1.389(14) . ?
C5 C10 1.513(14) . ?
C6 C7 1.374(17) . ?
C7 C8 1.374(16) . ?
C8 C9 1.396(13) . ?
C9 C13 1.515(14) . ?
C10 C11 1.526(14) . ?
C10 C12 1.529(13) . ?
C13 C14 1.518(14) . ?
C13 C15 1.530(14) . ?
C16 C21 1.397(14) . ?
C16 C17 1.411(14) . ?
C17 C18 1.394(13) . ?
C17 C22 1.524(14) . ?
C18 C19 1.369(16) . ?
C19 C20 1.369(16) . ?
C20 C21 1.391(13) . ?
C21 C25 1.529(14) . ?
C22 C24 1.531(15) . ?
C22 C23 1.534(14) . ?
C25 C26 1.526(15) . ?
C25 C27 1.531(13) . ?
C28 C29 1.397(16) . ?
C28 C35 1.527(15) . ?
C29 C30 1.507(17) . ?
C30 C31 1.49(2) . ?
C31 C32 1.526(16) . ?
C32 C33 1.451(15) . ?
C33 C34 1.502(14) . ?
C34 C35 1.492(18) . ?
C36 C37 1.389(15) . ?
C36 C41 1.398(15) . ?
C36 C42 1.483(18) . ?
C37 C38 1.388(17) . ?
C38 C39 1.371(16) . ?
C39 C40 1.387(15) . ?
C40 C41 1.376(17) . ?
C43 C49 1.32(3) . ?
C43 C44 1.41(3) . ?
C43 C48 1.39(3) . ?
C44 C45 1.36(3) . ?
C45 C46 1.12(3) . ?
C46 C47 1.73(5) . ?
C47 C48 1.28(4) . ?

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 C33 94.0(4) . . ?
C1 Ir1 C32 98.3(4) . . ?
C33 Ir1 C32 39.8(4) . . ?
C1 Ir1 C29 160.5(4) . . ?
C33 Ir1 C29 97.7(4) . . ?
C32 Ir1 C29 81.2(4) . . ?
C1 Ir1 C28 161.3(4) . . ?
C33 Ir1 C28 81.9(4) . . ?
C32 Ir1 C28 90.2(4) . . ?
C29 Ir1 C28 37.4(4) . . ?
C1 Ir1 Cl1 87.8(3) . . ?
C33 Ir1 Cl1 160.2(3) . . ?
C32 Ir1 Cl1 159.1(3) . . ?
C29 Ir1 Cl1 86.4(3) . . ?
C28 Ir1 Cl1 90.1(3) . . ?
C1 N1 C2 111.5(7) . . ?
C1 N1 C4 123.6(7) . . ?
C2 N1 C4 123.7(7) . . ?
C1 N2 C3 110.7(7) . . ?
C1 N2 C16 126.8(7) . . ?
C3 N2 C16 121.5(7) . . ?
N1 C1 N2 103.5(7) . . ?
N1 C1 Ir1 125.8(6) . . ?
N2 C1 Ir1 129.3(6) . . ?
C3 C2 N1 106.8(7) . . ?
C3 C2 Br1 128.4(7) . . ?
N1 C2 Br1 124.8(6) . . ?
C2 C3 N2 107.4(8) . . ?
C2 C3 Br2 128.6(7) . . ?
N2 C3 Br2 124.0(7) . . ?
C9 C4 C5 123.7(9) . . ?
C9 C4 N1 117.6(8) . . ?
C5 C4 N1 118.7(9) . . ?
C6 C5 C4 116.4(10) . . ?
C6 C5 C10 120.3(9) . . ?
C4 C5 C10 123.1(9) . . ?
C7 C6 C5 121.6(11) . . ?
C6 C7 C8 120.2(10) . . ?
C7 C8 C9 121.4(11) . . ?
C4 C9 C8 116.5(10) . . ?
C4 C9 C13 124.6(9) . . ?
C8 C9 C13 118.8(9) . . ?
C5 C10 C11 112.5(9) . . ?
C5 C10 C12 108.0(9) . . ?
C11 C10 C12 111.4(8) . . ?
C9 C13 C14 113.7(9) . . ?
C9 C13 C15 112.2(9) . . ?
C14 C13 C15 108.9(10) . . ?
C21 C16 C17 123.3(8) . . ?
C21 C16 N2 119.6(8) . . ?
C17 C16 N2 116.9(9) . . ?
C18 C17 C16 116.1(9) . . ?
C18 C17 C22 120.5(9) . . ?
C16 C17 C22 123.4(8) . . ?
C19 C18 C17 121.6(10) . . ?
C18 C19 C20 120.8(9) . . ?
C19 C20 C21 121.3(10) . . ?
C20 C21 C16 116.9(9) . . ?
C20 C21 C25 118.8(10) . . ?
C16 C21 C25 124.3(9) . . ?
C17 C22 C24 111.0(9) . . ?
C17 C22 C23 111.4(9) . . ?
C24 C22 C23 110.4(10) . . ?
C26 C25 C27 109.2(9) . . ?
C26 C25 C21 111.2(8) . . ?
C27 C25 C21 110.8(8) . . ?
C29 C28 C35 123.6(11) . . ?
C29 C28 Ir1 70.1(5) . . ?
C35 C28 Ir1 110.8(7) . . ?
C28 C29 C30 125.6(10) . . ?
C28 C29 Ir1 72.6(6) . . ?
C30 C29 Ir1 109.8(9) . . ?
C31 C30 C29 113.1(10) . . ?
C30 C31 C32 113.6(10) . . ?
C33 C32 C31 122.0(10) . . ?
C33 C32 Ir1 69.8(6) . . ?
C31 C32 Ir1 112.5(9) . . ?
C32 C33 C34 123.8(10) . . ?
C32 C33 Ir1 70.4(6) . . ?
C34 C33 Ir1 109.9(8) . . ?
C35 C34 C33 115.7(10) . . ?
C34 C35 C28 113.4(9) . . ?
C37 C36 C41 117.1(12) . . ?
C37 C36 C42 121.2(11) . . ?
C41 C36 C42 121.7(11) . . ?
C38 C37 C36 120.7(11) . . ?
C39 C38 C37 121.8(11) . . ?
C38 C39 C40 118.0(12) . . ?
C41 C40 C39 120.8(11) . . ?
C40 C41 C36 121.6(11) . . ?
C49 C43 C44 119(2) . . ?
C49 C43 C48 119(3) . . ?
C44 C43 C48 121(3) . . ?
C45 C44 C43 109(2) . . ?
C46 C45 C44 155(5) . . ?
C45 C46 C47 91(3) . . ?
C48 C47 C46 130(3) . . ?
C47 C48 C43 114(3) . . ?

_diffrn_measured_fraction_theta_max 0.819
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.937
_refine_diff_density_max         2.544
_refine_diff_density_min         -3.184
_refine_diff_density_rms         0.242

_database_code_depnum_ccdc_archive 'CCDC 831265'
#######################################################################
#
#                 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_publication_text

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            IDippBr.C7H8
_chemical_formula_moiety         'C27 H34 Br2 N2.C7H8'
_chemical_formula_sum            'C34 H42 Br2 N2'
_chemical_properties_physical    ?
_chemical_melting_point          375

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         638.52

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'
Br Br -0.2901 2.4595 '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'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

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

_cell_length_a                   10.4613(10)
_cell_length_b                   11.4351(9)
_cell_length_c                   15.2078(11)
_cell_angle_alpha                77.020(3)
_cell_angle_beta                 76.084(4)
_cell_angle_gamma                70.612(4)
_cell_volume                     1644.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    2.487
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_T_max  0.8857
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Apex'
_diffrn_measurement_method       'psi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19092
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0816
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         29.79
_reflns_number_total             7522
_reflns_number_gt                4728
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker AXS Collect Software'
_computing_cell_refinement       'Bruker Scalepack'
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2010'

_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)+(0.0545P)²+2.2549P] 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         7522
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Br1 Br 0.49711(5) -0.03534(4) 0.38032(3) 0.04039(15) Uani 1 1 d . . .
Br2 Br 0.49726(5) -0.03764(4) 0.13969(3) 0.04112(15) Uani 1 1 d . . .
N1 N 0.3994(3) 0.2240(3) 0.3011(2) 0.0237(7) Uani 1 1 d . . .
N2 N 0.4051(3) 0.2230(3) 0.1600(2) 0.0247(7) Uani 1 1 d . . .
C1 C 0.3729(4) 0.3048(4) 0.2216(3) 0.0252(8) Uani 1 1 d . . .
C2 C 0.4456(4) 0.0999(3) 0.2886(3) 0.0271(9) Uani 1 1 d . . .
C3 C 0.4488(4) 0.0986(4) 0.2009(3) 0.0284(9) Uani 1 1 d . . .
C4 C 0.3758(4) 0.2673(3) 0.3872(3) 0.0273(9) Uani 1 1 d . . .
C5 C 0.4850(5) 0.2907(4) 0.4106(3) 0.0345(10) Uani 1 1 d . . .
C6 C 0.4581(6) 0.3326(4) 0.4955(3) 0.0443(12) Uani 1 1 d . . .
H6 H 0.5285 0.3512 0.5143 0.053 Uiso 1 1 calc R . .
C7 C 0.3306(6) 0.3469(5) 0.5516(3) 0.0503(13) Uani 1 1 d . . .
H7 H 0.3146 0.3748 0.6086 0.060 Uiso 1 1 calc R . .
C8 C 0.2275(5) 0.3217(4) 0.5266(3) 0.0419(11) Uani 1 1 d . . .
H8 H 0.1413 0.3309 0.5670 0.050 Uiso 1 1 calc R . .
C9 C 0.2459(4) 0.2825(4) 0.4425(3) 0.0312(10) Uani 1 1 d . . .
C10 C 0.6229(5) 0.2739(5) 0.3476(3) 0.0425(11) Uani 1 1 d . . .
H10 H 0.6224 0.2260 0.3002 0.051 Uiso 1 1 calc R . .
C11 C 0.6397(7) 0.3982(6) 0.2969(5) 0.093(3) Uani 1 1 d . . .
H11A H 0.6338 0.4513 0.3411 0.139 Uiso 1 1 calc R . .
H11B H 0.5665 0.4396 0.2606 0.139 Uiso 1 1 calc R . .
H11C H 0.7296 0.3850 0.2561 0.139 Uiso 1 1 calc R . .
C12 C 0.7417(6) 0.1968(7) 0.3945(5) 0.084(2) Uani 1 1 d . . .
H12A H 0.7410 0.2358 0.4458 0.126 Uiso 1 1 calc R . .
H12B H 0.8283 0.1922 0.3507 0.126 Uiso 1 1 calc R . .
H12C H 0.7335 0.1119 0.4176 0.126 Uiso 1 1 calc R . .
C13 C 0.1294(5) 0.2579(4) 0.4155(3) 0.0403(11) Uani 1 1 d . . .
H13 H 0.1592 0.2444 0.3500 0.048 Uiso 1 1 calc R . .
C14 C -0.0012(6) 0.3701(5) 0.4205(5) 0.0754(19) Uani 1 1 d . . .
H14A H -0.0363 0.3832 0.4844 0.113 Uiso 1 1 calc R . .
H14B H -0.0713 0.3533 0.3965 0.113 Uiso 1 1 calc R . .
H14C H 0.0206 0.4455 0.3837 0.113 Uiso 1 1 calc R . .
C15 C 0.0975(6) 0.1394(5) 0.4717(5) 0.0691(18) Uani 1 1 d . . .
H15A H 0.1823 0.0690 0.4697 0.104 Uiso 1 1 calc R . .
H15B H 0.0304 0.1205 0.4460 0.104 Uiso 1 1 calc R . .
H15C H 0.0591 0.1524 0.5354 0.104 Uiso 1 1 calc R . .
C16 C 0.3921(4) 0.2631(3) 0.0652(3) 0.0271(9) Uani 1 1 d . . .
C17 C 0.2642(5) 0.2822(4) 0.0423(3) 0.0364(10) Uani 1 1 d . . .
C18 C 0.2528(6) 0.3197(4) -0.0500(3) 0.0440(12) Uani 1 1 d . . .
H18 H 0.1672 0.3343 -0.0680 0.053 Uiso 1 1 calc R . .
C19 C 0.3651(6) 0.3356(4) -0.1151(3) 0.0484(13) Uani 1 1 d . . .
H19 H 0.3560 0.3610 -0.1777 0.058 Uiso 1 1 calc R . .
C20 C 0.4889(6) 0.3156(4) -0.0913(3) 0.0422(12) Uani 1 1 d . . .
H20 H 0.5645 0.3277 -0.1377 0.051 Uiso 1 1 calc R . .
C21 C 0.5076(4) 0.2773(4) 0.0007(3) 0.0302(9) Uani 1 1 d . . .
C22 C 0.1404(5) 0.2670(5) 0.1150(4) 0.0474(12) Uani 1 1 d . . .
H22 H 0.1760 0.2167 0.1716 0.057 Uiso 1 1 calc R . .
C23 C 0.0492(6) 0.3941(6) 0.1388(5) 0.0776(19) Uani 1 1 d . . .
H23A H 0.1028 0.4347 0.1599 0.116 Uiso 1 1 calc R . .
H23B H -0.0284 0.3829 0.1875 0.116 Uiso 1 1 calc R . .
H23C H 0.0141 0.4469 0.0843 0.116 Uiso 1 1 calc R . .
C24 C 0.0582(7) 0.1967(6) 0.0890(5) 0.087(2) Uani 1 1 d . . .
H24A H 0.0230 0.2427 0.0330 0.130 Uiso 1 1 calc R . .
H24B H -0.0193 0.1893 0.1389 0.130 Uiso 1 1 calc R . .
H24C H 0.1177 0.1127 0.0785 0.130 Uiso 1 1 calc R . .
C25 C 0.6450(5) 0.2554(4) 0.0259(3) 0.0407(11) Uani 1 1 d . . .
H25 H 0.6353 0.2291 0.0939 0.049 Uiso 1 1 calc R . .
C26 C 0.6894(6) 0.3750(5) 0.0017(5) 0.0701(17) Uani 1 1 d . . .
H26A H 0.6967 0.4046 -0.0645 0.105 Uiso 1 1 calc R . .
H26B H 0.7790 0.3572 0.0191 0.105 Uiso 1 1 calc R . .
H26C H 0.6209 0.4399 0.0349 0.105 Uiso 1 1 calc R . .
C27 C 0.7570(6) 0.1488(5) -0.0192(4) 0.0614(15) Uani 1 1 d . . .
H27A H 0.7259 0.0737 -0.0051 0.092 Uiso 1 1 calc R . .
H27B H 0.8421 0.1300 0.0045 0.092 Uiso 1 1 calc R . .
H27C H 0.7745 0.1750 -0.0859 0.092 Uiso 1 1 calc R . .
C28 C 1.1071(11) 0.1309(18) -0.2204(7) 0.240(10) Uani 1 1 d . . .
H28A H 1.1425 0.1998 -0.2193 0.360 Uiso 1 1 calc R . .
H28B H 1.1748 0.0737 -0.2603 0.360 Uiso 1 1 calc R . .
H28C H 1.0906 0.0851 -0.1582 0.360 Uiso 1 1 calc R . .
C29 C 0.9831(14) 0.180(2) -0.2543(6) 0.176(8) Uani 1 1 d . . .
C30 C 0.9249(12) 0.1166(9) -0.2794(6) 0.104(3) Uani 1 1 d . . .
H30 H 0.9688 0.0288 -0.2754 0.125 Uiso 1 1 calc R . .
C31 C 0.7969(16) 0.1653(17) -0.3137(7) 0.154(6) Uani 1 1 d . . .
H31 H 0.7539 0.1142 -0.3303 0.184 Uiso 1 1 calc R . .
C32 C 0.7423(10) 0.2976(17) -0.3200(6) 0.132(4) Uani 1 1 d . . .
H32 H 0.6610 0.3451 -0.3438 0.159 Uiso 1 1 calc R . .
C33 C 0.832(2) 0.3577(11) -0.2828(9) 0.183(8) Uani 1 1 d . . .
H33 H 0.8004 0.4458 -0.2829 0.219 Uiso 1 1 calc R . .
C34 C 0.939(3) 0.2986(11) -0.2541(12) 0.32(2) Uani 1 1 d . . .
H34 H 0.9875 0.3397 -0.2322 0.386 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
Br1 C2 1.862(4) . ?
Br2 C3 1.858(4) . ?
N1 C1 1.372(5) . ?
N1 C2 1.381(5) . ?
N1 C4 1.440(5) . ?
N2 C1 1.379(5) . ?
N2 C3 1.388(5) . ?
N2 C16 1.436(5) . ?
C2 C3 1.328(6) . ?
C4 C9 1.395(6) . ?
C4 C5 1.395(6) . ?
C5 C6 1.410(6) . ?
C5 C10 1.507(6) . ?
C6 C7 1.380(7) . ?
C7 C8 1.356(7) . ?
C8 C9 1.398(6) . ?
C9 C13 1.502(6) . ?
C10 C12 1.499(7) . ?
C10 C11 1.501(7) . ?
C13 C15 1.524(7) . ?
C13 C14 1.532(7) . ?
C16 C21 1.392(6) . ?
C16 C17 1.398(6) . ?
C17 C18 1.394(6) . ?
C17 C22 1.518(7) . ?
C18 C19 1.377(7) . ?
C19 C20 1.361(7) . ?
C20 C21 1.410(6) . ?
C21 C25 1.502(6) . ?
C22 C23 1.518(7) . ?
C22 C24 1.519(8) . ?
C25 C26 1.529(7) . ?
C25 C27 1.539(6) . ?
C28 C29 1.404(15) . ?
C29 C30 1.252(14) . ?
C29 C34 1.28(2) . ?
C30 C31 1.444(15) . ?
C31 C32 1.419(16) . ?
C32 C33 1.59(2) . ?
C33 C34 1.22(3) . ?

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 N1 C2 112.3(3) . . ?
C1 N1 C4 122.3(3) . . ?
C2 N1 C4 125.3(3) . . ?
C1 N2 C3 112.0(3) . . ?
C1 N2 C16 123.4(3) . . ?
C3 N2 C16 124.7(3) . . ?
N1 C1 N2 101.8(3) . . ?
C3 C2 N1 107.2(3) . . ?
C3 C2 Br1 128.6(3) . . ?
N1 C2 Br1 124.2(3) . . ?
C2 C3 N2 106.7(3) . . ?
C2 C3 Br2 129.2(3) . . ?
N2 C3 Br2 124.1(3) . . ?
C9 C4 C5 123.8(4) . . ?
C9 C4 N1 118.3(4) . . ?
C5 C4 N1 117.9(4) . . ?
C4 C5 C6 116.3(4) . . ?
C4 C5 C10 121.4(4) . . ?
C6 C5 C10 122.3(4) . . ?
C7 C6 C5 120.7(4) . . ?
C8 C7 C6 121.1(5) . . ?
C7 C8 C9 121.3(5) . . ?
C4 C9 C8 116.8(4) . . ?
C4 C9 C13 122.8(4) . . ?
C8 C9 C13 120.3(4) . . ?
C12 C10 C11 112.7(5) . . ?
C12 C10 C5 113.4(4) . . ?
C11 C10 C5 110.9(4) . . ?
C9 C13 C15 112.3(4) . . ?
C9 C13 C14 112.2(4) . . ?
C15 C13 C14 110.3(4) . . ?
C21 C16 C17 123.4(4) . . ?
C21 C16 N2 118.7(4) . . ?
C17 C16 N2 117.9(4) . . ?
C18 C17 C16 117.6(4) . . ?
C18 C17 C22 120.8(4) . . ?
C16 C17 C22 121.6(4) . . ?
C19 C18 C17 120.2(5) . . ?
C20 C19 C18 121.2(4) . . ?
C19 C20 C21 121.5(5) . . ?
C16 C21 C20 116.1(4) . . ?
C16 C21 C25 123.0(4) . . ?
C20 C21 C25 120.9(4) . . ?
C23 C22 C17 110.2(4) . . ?
C23 C22 C24 111.1(5) . . ?
C17 C22 C24 113.6(5) . . ?
C21 C25 C26 111.7(4) . . ?
C21 C25 C27 111.7(4) . . ?
C26 C25 C27 110.3(4) . . ?
C30 C29 C34 126(2) . . ?
C30 C29 C28 125(2) . . ?
C34 C29 C28 109.1(19) . . ?
C29 C30 C31 125.7(13) . . ?
C32 C31 C30 112.8(10) . . ?
C31 C32 C33 112.6(11) . . ?
C34 C33 C32 124.7(16) . . ?
C33 C34 C29 118(3) . . ?

_diffrn_measured_fraction_theta_max 0.800
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         1.373
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.089

_database_code_depnum_ccdc_archive 'CCDC 831266'
