# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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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# 
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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_BVW105

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


_audit_creation_method           'SHELXL, adapted and expanded'
_audit_creation_date             2006-07-27
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 Cl Ir N2 O2'
_chemical_formula_weight         435.91

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   13.3567(15)
_cell_length_b                   13.2668(5)
_cell_length_c                   16.9665(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.554(8)
_cell_angle_gamma                90.00
_cell_volume                     2910.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    208(2)
_cell_measurement_reflns_used    462
_cell_measurement_theta_min      2.200
_cell_measurement_theta_max      27.510

_exptl_crystal_description       'rough plate'
_exptl_crystal_colour            'colorless translucent'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
#_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.990
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    9.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.385
_exptl_absorpt_correction_T_max  0.688

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      208(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       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector \f and \w scan'
_diffrn_detector_area_resol_mean 18.4
_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0.000
_diffrn_reflns_number            71329
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.51
_reflns_number_total             6675
_reflns_number_gt                5635
_reflns_number_observed          5635
_reflns_threshold_expression     >2sigma(I)
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_cell_refinement       ?
_computing_data_reduction        
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_structure_solution    
;
DIRDIF (Beurskens et al., 1996),
PATTY (Beurskens et al., 1987)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek, 2003)
;
_computing_publication_material  ?

_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     
;
w=1/[\s^2^(Fo^2^)+(0.0138P)^2^+3.6163P] 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         6675
_refine_ls_number_parameters     343
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0211
_refine_ls_R_factor_obs          0.0211
_refine_ls_wR_factor_ref         0.0473
_refine_ls_wR_factor_all         0.0473
_refine_ls_wR_factor_gt          0.0428
_refine_ls_wR_factor_obs         0.0428
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_goodness_of_fit_all   1.070
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.003
_refine_ls_shift/esd_max         0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_shift/esd_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1A Ir 0.168606(11) 0.709391(11) 0.549773(8) 0.03436(5) Uani 1 d D . .
N1A N 0.3465(2) 0.8494(2) 0.63561(17) 0.0328(6) Uani 1 d . . .
N2A N 0.2555(2) 0.8059(2) 0.71755(18) 0.0374(7) Uani 1 d . . .
C1A C 0.2654(3) 0.7923(3) 0.6413(2) 0.0319(7) Uani 1 d . . .
C2A C 0.3855(3) 0.9002(3) 0.7076(2) 0.0397(9) Uani 1 d . . .
H2A H 0.4416 0.9453 0.7188 0.048 Uiso 1 calc R . .
C3A C 0.3285(3) 0.8732(3) 0.7583(2) 0.0415(9) Uani 1 d . . .
H3A H 0.3368 0.8960 0.8120 0.050 Uiso 1 calc R . .
C4A C 0.3812(3) 0.8628(3) 0.5608(2) 0.0364(8) Uani 1 d . . .
H4A H 0.3466 0.8109 0.5214 0.044 Uiso 1 calc R . .
C5A C 0.3477(3) 0.9651(3) 0.5242(2) 0.0490(10) Uani 1 d . . .
H5A H 0.2731 0.9710 0.5134 0.074 Uiso 1 calc R . .
H5B H 0.3685 0.9725 0.4736 0.074 Uiso 1 calc R . .
H5C H 0.3802 1.0174 0.5619 0.074 Uiso 1 calc R . .
C6A C 0.4963(3) 0.8463(3) 0.5773(2) 0.0472(10) Uani 1 d . . .
H6A H 0.5322 0.8967 0.6155 0.071 Uiso 1 calc R . .
H6B H 0.5174 0.8520 0.5268 0.071 Uiso 1 calc R . .
H6C H 0.5135 0.7796 0.6002 0.071 Uiso 1 calc R . .
C7A C 0.1756(3) 0.7569(3) 0.7507(2) 0.0445(10) Uani 1 d . . .
H7A H 0.1285 0.7196 0.7059 0.053 Uiso 1 calc R . .
C8A C 0.2232(4) 0.6835(5) 0.8150(3) 0.0820(17) Uani 1 d . . .
H8A H 0.2609 0.6332 0.7925 0.123 Uiso 1 calc R . .
H8B H 0.1694 0.6509 0.8350 0.123 Uiso 1 calc R . .
H8C H 0.2703 0.7184 0.8594 0.123 Uiso 1 calc R . .
C9A C 0.1135(5) 0.8357(4) 0.7803(5) 0.104(2) Uani 1 d . . .
H9A H 0.1558 0.8673 0.8289 0.156 Uiso 1 calc R . .
H9B H 0.0537 0.8045 0.7929 0.156 Uiso 1 calc R . .
H9C H 0.0908 0.8862 0.7382 0.156 Uiso 1 calc R . .
C10A C 0.0727(3) 0.6371(3) 0.4691(2) 0.0494(10) Uani 1 d D . .
O10A O 0.0122(3) 0.5938(3) 0.4232(2) 0.0755(11) Uani 1 d D . .
Cl1A Cl 0.0600(4) 0.8498(4) 0.5301(4) 0.0594(15) Uani 0.611(11) d PD A 1
C11A C 0.2604(15) 0.6029(13) 0.5655(11) 0.056(4) Uani 0.611(11) d PD A 1
O11A O 0.3116(9) 0.5363(8) 0.5792(7) 0.080(3) Uani 0.611(11) d PD A 1
Cl2A Cl 0.2824(7) 0.5733(6) 0.5810(6) 0.071(2) Uani 0.389(11) d PD A 2
C12A C 0.083(3) 0.820(2) 0.529(2) 0.069(9) Uani 0.389(11) d PD A 2
O12A O 0.0293(14) 0.8832(12) 0.5160(12) 0.084(5) Uani 0.389(11) d PD A 2
Ir1B Ir 0.179829(10) 0.240913(10) 0.177089(8) 0.02925(4) Uani 1 d . . .
Cl1B Cl 0.05998(8) 0.37305(8) 0.16243(7) 0.0530(3) Uani 1 d . . .
N1B N 0.3588(2) 0.3776(2) 0.26569(17) 0.0313(6) Uani 1 d . . .
N2B N 0.2650(2) 0.3360(2) 0.34622(16) 0.0320(6) Uani 1 d . . .
C1B C 0.2750(2) 0.3236(2) 0.2696(2) 0.0281(7) Uani 1 d . . .
C2B C 0.4003(3) 0.4237(3) 0.3392(2) 0.0369(8) Uani 1 d . . .
H2B H 0.4588 0.4657 0.3518 0.044 Uiso 1 calc R . .
C3B C 0.3422(3) 0.3980(3) 0.3893(2) 0.0375(8) Uani 1 d . . .
H3B H 0.3520 0.4184 0.4437 0.045 Uiso 1 calc R . .
C4B C 0.3952(3) 0.3915(3) 0.1917(2) 0.0381(8) Uani 1 d . . .
H4B H 0.3549 0.3458 0.1493 0.046 Uiso 1 calc R . .
C5B C 0.3736(4) 0.4985(3) 0.1618(3) 0.0559(11) Uani 1 d . . .
H5D H 0.2999 0.5116 0.1504 0.084 Uiso 1 calc R . .
H5E H 0.3968 0.5078 0.1125 0.084 Uiso 1 calc R . .
H5F H 0.4103 0.5449 0.2033 0.084 Uiso 1 calc R . .
C6B C 0.5079(3) 0.3632(4) 0.2071(3) 0.0640(13) Uani 1 d . . .
H6D H 0.5490 0.4074 0.2483 0.096 Uiso 1 calc R . .
H6E H 0.5299 0.3701 0.1570 0.096 Uiso 1 calc R . .
H6F H 0.5172 0.2939 0.2258 0.096 Uiso 1 calc R . .
C7B C 0.1843(3) 0.2892(3) 0.3786(2) 0.0368(8) Uani 1 d . . .
H7B H 0.1431 0.2445 0.3358 0.044 Uiso 1 calc R . .
C8B C 0.2325(4) 0.2242(4) 0.4518(3) 0.0603(13) Uani 1 d . . .
H8D H 0.2748 0.1724 0.4360 0.090 Uiso 1 calc R . .
H8E H 0.1783 0.1929 0.4721 0.090 Uiso 1 calc R . .
H8F H 0.2753 0.2658 0.4942 0.090 Uiso 1 calc R . .
C9B C 0.1128(4) 0.3694(4) 0.3964(3) 0.0647(13) Uani 1 d . . .
H9D H 0.1498 0.4108 0.4415 0.097 Uiso 1 calc R . .
H9E H 0.0543 0.3376 0.4106 0.097 Uiso 1 calc R . .
H9F H 0.0883 0.4112 0.3486 0.097 Uiso 1 calc R . .
C10B C 0.0901(3) 0.1687(3) 0.0928(2) 0.0416(9) Uani 1 d . . .
O10B O 0.0364(3) 0.1237(2) 0.04321(18) 0.0678(10) Uani 1 d . . .
C11B C 0.2784(3) 0.1410(3) 0.1932(2) 0.0456(10) Uani 1 d . . .
O11B O 0.3374(3) 0.0829(3) 0.2049(2) 0.0725(10) Uani 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
Ir1A 0.03180(8) 0.03844(9) 0.03122(8) -0.00117(6) 0.00489(6) -0.00507(6)
N1A 0.0310(16) 0.0329(16) 0.0337(16) 0.0003(12) 0.0067(12) -0.0047(12)
N2A 0.0326(16) 0.0471(19) 0.0316(16) 0.0006(14) 0.0061(13) -0.0041(14)
C1A 0.0312(18) 0.0333(19) 0.0299(18) 0.0014(14) 0.0051(14) -0.0001(14)
C2A 0.038(2) 0.041(2) 0.037(2) -0.0059(17) 0.0039(16) -0.0084(16)
C3A 0.036(2) 0.054(2) 0.033(2) -0.0068(17) 0.0063(16) -0.0063(17)
C4A 0.039(2) 0.036(2) 0.0347(19) -0.0018(15) 0.0102(16) -0.0089(16)
C5A 0.050(3) 0.048(2) 0.049(2) 0.0138(19) 0.013(2) 0.0017(19)
C6A 0.045(2) 0.048(2) 0.053(2) 0.0058(19) 0.0187(19) 0.0018(18)
C7A 0.038(2) 0.060(3) 0.038(2) 0.0022(18) 0.0135(17) -0.0108(18)
C8A 0.065(3) 0.105(5) 0.084(4) 0.036(3) 0.034(3) -0.010(3)
C9A 0.084(4) 0.077(4) 0.184(7) 0.005(4) 0.094(5) 0.005(3)
C10A 0.045(2) 0.055(3) 0.041(2) -0.0069(19) -0.0006(19) -0.001(2)
O10A 0.061(2) 0.082(3) 0.067(2) -0.0296(19) -0.0141(17) -0.0052(18)
Cl1A 0.047(3) 0.061(3) 0.0629(18) 0.005(2) -0.0001(19) 0.0113(19)
C11A 0.056(10) 0.069(13) 0.040(7) -0.010(6) 0.007(7) -0.011(7)
O11A 0.082(7) 0.056(6) 0.089(5) -0.009(5) -0.003(5) 0.015(4)
Cl2A 0.068(5) 0.054(6) 0.074(4) -0.008(4) -0.011(3) 0.008(3)
C12A 0.035(13) 0.11(3) 0.053(10) -0.029(15) -0.010(9) 0.002(12)
O12A 0.090(11) 0.067(9) 0.085(10) -0.001(7) 0.002(8) 0.035(7)
Ir1B 0.02983(7) 0.02796(7) 0.02767(7) -0.00086(5) 0.00297(5) -0.00266(5)
Cl1B 0.0474(6) 0.0478(6) 0.0569(6) 0.0009(5) 0.0001(5) 0.0107(5)
N1B 0.0285(15) 0.0286(15) 0.0359(16) -0.0029(12) 0.0060(12) -0.0025(12)
N2B 0.0359(16) 0.0298(15) 0.0287(15) -0.0027(12) 0.0052(12) -0.0001(12)
C1B 0.0270(17) 0.0244(16) 0.0313(17) 0.0000(13) 0.0041(14) 0.0015(13)
C2B 0.0326(19) 0.034(2) 0.039(2) -0.0087(15) -0.0008(16) -0.0061(15)
C3B 0.040(2) 0.037(2) 0.0314(19) -0.0056(15) 0.0002(16) 0.0010(16)
C4B 0.035(2) 0.042(2) 0.038(2) -0.0003(16) 0.0097(16) -0.0051(16)
C5B 0.064(3) 0.052(3) 0.051(3) 0.012(2) 0.012(2) -0.003(2)
C6B 0.048(3) 0.083(4) 0.066(3) 0.012(3) 0.024(2) 0.018(2)
C7B 0.041(2) 0.034(2) 0.036(2) 0.0003(15) 0.0119(16) -0.0060(16)
C8B 0.069(3) 0.060(3) 0.049(3) 0.018(2) 0.008(2) -0.009(2)
C9B 0.064(3) 0.057(3) 0.087(4) -0.002(3) 0.045(3) 0.003(2)
C10B 0.047(2) 0.035(2) 0.035(2) 0.0085(16) -0.0032(17) 0.0003(17)
O10B 0.079(2) 0.0518(19) 0.0506(18) -0.0023(15) -0.0242(17) -0.0122(17)
C11B 0.047(2) 0.045(2) 0.041(2) -0.0144(18) 0.0039(19) -0.005(2)
O11B 0.057(2) 0.062(2) 0.087(3) -0.0204(19) -0.0024(18) 0.0136(17)

_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
Ir1A C12A 1.843(13) . Y
Ir1A C11A 1.846(11) . Y
Ir1A C10A 1.885(4) . Y
Ir1A C1A 2.070(3) . Y
Ir1A Cl1A 2.333(4) . Y
Ir1A Cl2A 2.333(6) . Y
N1A C1A 1.346(4) . Y
N1A C2A 1.377(4) . Y
N1A C4A 1.467(4) . Y
N2A C1A 1.344(4) . Y
N2A C3A 1.374(5) . Y
N2A C7A 1.476(5) . Y
C2A C3A 1.334(5) . Y
C4A C6A 1.508(5) . Y
C4A C5A 1.514(5) . Y
C7A C8A 1.480(6) . Y
C7A C9A 1.496(7) . Y
C10A O10A 1.128(4) . Y
C11A O11A 1.106(14) . Y
C12A O12A 1.086(15) . Y
Ir1B C11B 1.840(5) . Y
Ir1B C10B 1.881(4) . Y
Ir1B C1B 2.069(3) . Y
Ir1B Cl1B 2.3446(10) . Y
N1B C1B 1.345(4) . Y
N1B C2B 1.375(4) . Y
N1B C4B 1.467(5) . Y
N2B C1B 1.349(4) . Y
N2B C3B 1.376(4) . Y
N2B C7B 1.466(4) . Y
C2B C3B 1.330(5) . Y
C4B C6B 1.509(5) . Y
C4B C5B 1.511(5) . Y
C7B C9B 1.510(5) . Y
C7B C8B 1.515(5) . Y
C10B O10B 1.129(4) . Y
C11B O11B 1.084(5) . Y

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
C12A Ir1A C11A 175.6(16) . . Y
C12A Ir1A C10A 89.7(11) . . Y
C11A Ir1A C10A 91.2(7) . . Y
C12A Ir1A C1A 87.5(11) . . Y
C11A Ir1A C1A 91.8(7) . . Y
C10A Ir1A C1A 176.07(16) . . Y
C12A Ir1A Cl1A 2.5(14) . . Y
C11A Ir1A Cl1A 176.9(8) . . Y
C10A Ir1A Cl1A 91.0(2) . . Y
C1A Ir1A Cl1A 86.11(18) . . Y
C12A Ir1A Cl2A 177.0(11) . . Y
C11A Ir1A Cl2A 5.0(8) . . Y
C10A Ir1A Cl2A 93.2(3) . . Y
C1A Ir1A Cl2A 89.5(3) . . Y
Cl1A Ir1A Cl2A 175.1(3) . . Y
C1A N1A C2A 110.1(3) . . Y
C1A N1A C4A 124.4(3) . . Y
C2A N1A C4A 125.2(3) . . Y
C1A N2A C3A 110.0(3) . . Y
C1A N2A C7A 124.3(3) . . Y
C3A N2A C7A 125.7(3) . . Y
N2A C1A N1A 105.6(3) . . Y
N2A C1A Ir1A 126.8(3) . . Y
N1A C1A Ir1A 127.4(3) . . Y
C3A C2A N1A 106.9(3) . . Y
C2A C3A N2A 107.3(3) . . Y
N1A C4A C6A 110.6(3) . . Y
N1A C4A C5A 109.8(3) . . Y
C6A C4A C5A 112.8(3) . . Y
N2A C7A C8A 110.6(3) . . Y
N2A C7A C9A 109.6(4) . . Y
C8A C7A C9A 112.6(5) . . Y
O10A C10A Ir1A 176.6(4) . . Y
O11A C11A Ir1A 175(2) . . Y
O12A C12A Ir1A 177(4) . . Y
C11B Ir1B C10B 92.39(16) . . Y
C11B Ir1B C1B 89.37(14) . . Y
C10B Ir1B C1B 178.23(15) . . Y
C11B Ir1B Cl1B 176.88(12) . . Y
C10B Ir1B Cl1B 90.73(12) . . Y
C1B Ir1B Cl1B 87.51(9) . . Y
C1B N1B C2B 110.0(3) . . Y
C1B N1B C4B 124.7(3) . . Y
C2B N1B C4B 125.2(3) . . Y
C1B N2B C3B 110.0(3) . . Y
C1B N2B C7B 124.8(3) . . Y
C3B N2B C7B 125.3(3) . . Y
N1B C1B N2B 105.6(3) . . Y
N1B C1B Ir1B 127.2(2) . . Y
N2B C1B Ir1B 127.2(2) . . Y
C3B C2B N1B 107.4(3) . . Y
C2B C3B N2B 107.1(3) . . Y
N1B C4B C6B 110.5(3) . . Y
N1B C4B C5B 109.3(3) . . Y
C6B C4B C5B 112.9(4) . . Y
N2B C7B C9B 109.7(3) . . Y
N2B C7B C8B 110.3(3) . . Y
C9B C7B C8B 113.4(4) . . Y
O10B C10B Ir1B 178.6(3) . . Y
O11B C11B Ir1B 178.0(4) . . Y

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 945707'
#######################################################################
#
#                 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_BVW117

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


_audit_creation_method           'SHELXL, adapted and expanded'
_audit_creation_date             2006-07-27
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 Cl Ir N2 O2'
_chemical_formula_weight         437.92

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   12.653(3)
_cell_length_b                   10.3696(6)
_cell_length_c                   11.3896(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.162(16)
_cell_angle_gamma                90.00
_cell_volume                     1442.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    208(2)
_cell_measurement_reflns_used    348
_cell_measurement_theta_min      2.580
_cell_measurement_theta_max      27.500

_exptl_crystal_description       'rough fragment'
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
#_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    9.434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.095
_exptl_absorpt_correction_T_max  0.167

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      208(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       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector \f and \w scan'
_diffrn_detector_area_resol_mean 18.4
_diffrn_standards_number         0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0.000
_diffrn_reflns_number            19289
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1665
_reflns_number_gt                1621
_reflns_number_observed          1621
_reflns_threshold_expression     >2sigma(I)
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_cell_refinement       ?
_computing_data_reduction        
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_structure_solution    
;
DIRDIF (Beurskens et al., 1996),
PATTY (Beurskens et al., 1987)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
PLATON (Spek, 2003)
;
_computing_publication_material  ?

_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     
;
w=1/[\s^2^(Fo^2^)+(0.0106P)^2^+0.4578P] 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         1665
_refine_ls_number_parameters     95
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0110
_refine_ls_R_factor_gt           0.0101
_refine_ls_R_factor_obs          0.0101
_refine_ls_wR_factor_ref         0.0258
_refine_ls_wR_factor_all         0.0258
_refine_ls_wR_factor_gt          0.0252
_refine_ls_wR_factor_obs         0.0252
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_goodness_of_fit_all   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_shift/esd_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.0000 0.177338(7) 0.2500 0.02384(4) Uani 1 d S . .
O1 O 0.0000 -0.11453(18) 0.2500 0.0533(6) Uani 1 d S . .
C1 C 0.0000 0.3775(2) 0.2500 0.0253(5) Uani 1 d S . .
N2 N -0.07220(12) 0.45063(13) 0.17276(14) 0.0296(3) Uani 1 d . . .
C3 C -0.05491(17) 0.58824(16) 0.20288(19) 0.0378(4) Uani 1 d . . .
H3A H -0.1128 0.6225 0.2368 0.045 Uiso 1 calc R . .
H3B H -0.0520 0.6390 0.1312 0.045 Uiso 1 calc R . .
C4 C -0.17278(15) 0.40122(18) 0.08922(17) 0.0332(4) Uani 1 d . . .
H4 H -0.1585 0.3113 0.0685 0.040 Uiso 1 calc R . .
C5 C -0.2004(2) 0.4786(2) -0.0280(2) 0.0516(5) Uani 1 d . . .
H5A H -0.2209 0.5656 -0.0116 0.077 Uiso 1 calc R . .
H5B H -0.2609 0.4380 -0.0865 0.077 Uiso 1 calc R . .
H5C H -0.1371 0.4817 -0.0609 0.077 Uiso 1 calc R . .
C6 C -0.26633(17) 0.3982(2) 0.1495(2) 0.0461(5) Uani 1 d . . .
H6A H -0.2469 0.3431 0.2207 0.069 Uiso 1 calc R . .
H6B H -0.3315 0.3647 0.0926 0.069 Uiso 1 calc R . .
H6C H -0.2805 0.4848 0.1737 0.069 Uiso 1 calc R . .
C7 C 0.0000 -0.0060(2) 0.2500 0.0329(6) Uani 1 d S . .
Cl1 Cl -0.0624(2) 0.1909(2) 0.4249(2) 0.0442(5) Uani 0.50 d P A 1
C8 C -0.0482(8) 0.1776(9) 0.3878(9) 0.0383(17) Uani 0.50 d P A 2
O2 O -0.0788(5) 0.1805(4) 0.4726(5) 0.0601(15) Uani 0.50 d P A 2

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 0.02599(6) 0.01744(6) 0.02745(6) 0.000 0.00586(4) 0.000
O1 0.0793(16) 0.0190(10) 0.0692(16) 0.000 0.0329(13) 0.000
C1 0.0295(11) 0.0190(11) 0.0282(12) 0.000 0.0087(9) 0.000
N2 0.0334(8) 0.0183(7) 0.0339(8) -0.0006(6) 0.0033(6) 0.0037(6)
C3 0.0529(12) 0.0178(8) 0.0406(11) 0.0012(7) 0.0084(9) 0.0035(8)
C4 0.0325(9) 0.0304(9) 0.0328(9) -0.0021(7) 0.0017(7) 0.0051(7)
C5 0.0530(13) 0.0617(14) 0.0345(11) 0.0079(10) 0.0017(9) 0.0041(11)
C6 0.0368(10) 0.0538(13) 0.0466(12) 0.0003(10) 0.0088(9) 0.0030(10)
C7 0.0389(14) 0.0239(13) 0.0370(14) 0.000 0.0119(11) 0.000
Cl1 0.0616(11) 0.0349(8) 0.0448(16) -0.0049(9) 0.0296(10) -0.0090(6)
C8 0.045(4) 0.025(3) 0.046(5) -0.005(3) 0.015(3) -0.009(2)
O2 0.090(4) 0.051(3) 0.051(3) -0.013(2) 0.038(3) -0.0227(19)

_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 1.826(9) 2 Y
Ir1 C8 1.826(9) . Y
Ir1 C7 1.901(3) . Y
Ir1 C1 2.076(2) . Y
Ir1 Cl1 2.332(2) 2 Y
Ir1 Cl1 2.332(2) . Y
O1 C7 1.125(3) . Y
C1 N2 1.3279(19) . Y
C1 N2 1.3279(19) 2 Y
N2 C4 1.468(2) . Y
N2 C3 1.471(2) . Y
C3 C3 1.518(4) 2 Y
C4 C6 1.516(3) . Y
C4 C5 1.518(3) . Y
C8 O2 1.132(8) . Y

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 C8 179.9(6) 2 . Y
C8 Ir1 C7 90.1(3) 2 . Y
C8 Ir1 C7 90.1(3) . . Y
C8 Ir1 C1 89.9(3) 2 . Y
C8 Ir1 C1 89.9(3) . . Y
C7 Ir1 C1 180.0 . . ?
C8 Ir1 Cl1 3.4(3) 2 2 Y
C8 Ir1 Cl1 176.5(2) . 2 Y
C7 Ir1 Cl1 93.46(6) . 2 Y
C1 Ir1 Cl1 86.54(6) . 2 Y
C8 Ir1 Cl1 176.4(2) 2 . Y
C8 Ir1 Cl1 3.4(3) . . Y
C7 Ir1 Cl1 93.46(6) . . Y
C1 Ir1 Cl1 86.54(6) . . Y
Cl1 Ir1 Cl1 173.07(12) 2 . Y
N2 C1 N2 110.3(2) . 2 Y
N2 C1 Ir1 124.83(10) . . Y
N2 C1 Ir1 124.83(10) 2 . Y
C1 N2 C4 124.04(15) . . Y
C1 N2 C3 111.41(15) . . Y
C4 N2 C3 122.74(15) . . Y
N2 C3 C3 102.58(10) . 2 Y
N2 C4 C6 111.16(16) . . Y
N2 C4 C5 110.31(16) . . Y
C6 C4 C5 112.44(17) . . Y
O1 C7 Ir1 180.0 . . ?
O2 C8 Ir1 178.4(9) . . Y

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.938
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 945708'