data_rob296f1
_audit_creation_date              2013-04-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_chemical_name_common             ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety          'C13 H22 Cl2 Ir N'
_chemical_formula_sum             'C13 H22 Cl2 Ir N'
_chemical_formula_weight          455.42
_chemical_melting_point           ?
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'
 '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'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, y+1/2, -z+1/2'
 3 '-x, -y, -z'
 4 'x, -y-1/2, z-1/2'

_cell_length_a                    8.3771(8)
_cell_length_b                    25.957(3)
_cell_length_c                    8.0905(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  116.833(4)
_cell_angle_gamma                 90.00
_cell_volume                      1569.8(3)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     9993
_cell_measurement_temperature     110(2)
_cell_measurement_theta_max       26.15
_cell_measurement_theta_min       2.72
_exptl_absorpt_coefficient_mu     8.826
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_correction_T_min   0.5033
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.6752.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour             yellow
_exptl_crystal_colour_primary     yellow
_exptl_crystal_density_diffrn     1.927
_exptl_crystal_density_meas       .
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        ?
_exptl_crystal_F_000              872
_exptl_crystal_size_max           0.21
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.1
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0329
_diffrn_reflns_av_unetI/netI      0.0204
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_k_max        30
_diffrn_reflns_limit_k_min        -30
_diffrn_reflns_limit_l_max        9
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_number             23217
_diffrn_reflns_theta_full         25.00
_diffrn_reflns_theta_max          25.03
_diffrn_reflns_theta_min          2.84
_diffrn_ambient_temperature       110(2)
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        '\f and \w scans'
_diffrn_radiation_monochromator   'graphite'
_diffrn_radiation_type            'MoK\a'
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'fine-focus sealed tube'
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          0
_reflns_number_gt                 2589
_reflns_number_total              2752
_reflns_threshold_expression      >2sigma(I)
_computing_cell_refinement        ?
_computing_data_collection        ?
_computing_data_reduction         'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max          1.288
_refine_diff_density_min          -1.624
_refine_diff_density_rms          0.113
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.214
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      159
_refine_ls_number_reflns          2752
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0283
_refine_ls_R_factor_gt            0.0251
_refine_ls_restrained_S_all       1.214
_refine_ls_shift/su_max           0.003
_refine_ls_shift/su_mean          0.001
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+6.5253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0452
_refine_ls_wR_factor_ref          0.0460
_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. 
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H11A,H11B} of C11, {H10A,H10B} of C10, {H12A,H12B} of C12, H1 of N1
 At 1.5 times of:
  {H6A,H6B,H6C} of C6, {H13A,H13B,H13C} of C13, {H7A,H7B,H7C} of C7, {H8A,H8B,
  H8C} of C8, {H9A,H9B,H9C} of C9
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens    geom
_atom_sites_solution_primary      iterative
_atom_sites_solution_secondary    difmap
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 0.05773(2) 0.621883(7) 0.03439(2) 0.01783(7) Uani 1 1 d . . .
 Cl1 Cl -0.16125(16) 0.56282(5) -0.18832(17) 0.0277(3) Uani 1 1 d . . .
 Cl2 Cl 0.1365(2) 0.65250(5) -0.20396(18) 0.0337(3) Uani 1 1 d . . .
 C10 C 0.3308(7) 0.6198(2) 0.4754(7) 0.0293(12) Uani 1 1 d . . .
 H10A H 0.3137 0.6185 0.5887 0.035 Uiso 1 1 calc R . .
 H10B H 0.4349 0.6424 0.5022 0.035 Uiso 1 1 calc R . .
 N1 N 0.2377(5) 0.55672(15) 0.0846(5) 0.0228(9) Uani 1 1 d . . .
 H1 H 0.1765 0.5289 0.1012 0.027 Uiso 1 1 calc R . .
 C2 C -0.0170(6) 0.62522(19) 0.2579(6) 0.0235(11) Uani 1 1 d . . .
 C12 C 0.4060(7) 0.5602(2) 0.2621(7) 0.0303(12) Uani 1 1 d . . .
 H12A H 0.4750 0.5905 0.2564 0.036 Uiso 1 1 calc R . .
 H12B H 0.4792 0.5291 0.2743 0.036 Uiso 1 1 calc R . .
 C5 C 0.1627(7) 0.68832(18) 0.2106(7) 0.0233(11) Uani 1 1 d . . .
 C3 C -0.1328(7) 0.66035(19) 0.1093(7) 0.0247(11) Uani 1 1 d . . .
 C4 C -0.0254(7) 0.69803(18) 0.0778(7) 0.0252(11) Uani 1 1 d . . .
 C1 C 0.1663(6) 0.64440(19) 0.3220(6) 0.0229(11) Uani 1 1 d . . .
 C11 C 0.3762(7) 0.5647(2) 0.4348(7) 0.0329(13) Uani 1 1 d . . .
 H11A H 0.4856 0.5527 0.5432 0.040 Uiso 1 1 calc R . .
 H11B H 0.2775 0.5413 0.4205 0.040 Uiso 1 1 calc R . .
 C7 C -0.3334(7) 0.6557(2) 0.0059(8) 0.0389(14) Uani 1 1 d . . .
 H7A H -0.3779 0.6764 -0.1075 0.058 Uiso 1 1 calc R . .
 H7B H -0.3866 0.6682 0.0843 0.058 Uiso 1 1 calc R . .
 H7C H -0.3663 0.6196 -0.0264 0.058 Uiso 1 1 calc R . .
 C8 C -0.0906(8) 0.7419(2) -0.0588(8) 0.0382(14) Uani 1 1 d . . .
 H8A H -0.0094 0.7466 -0.1148 0.057 Uiso 1 1 calc R . .
 H8B H -0.0938 0.7736 0.0054 0.057 Uiso 1 1 calc R . .
 H8C H -0.2111 0.7342 -0.1559 0.057 Uiso 1 1 calc R . .
 C9 C 0.3191(7) 0.7212(2) 0.2305(8) 0.0313(13) Uani 1 1 d . . .
 H9A H 0.4309 0.7024 0.3017 0.047 Uiso 1 1 calc R . .
 H9B H 0.3200 0.7532 0.2952 0.047 Uiso 1 1 calc R . .
 H9C H 0.3079 0.7294 0.1075 0.047 Uiso 1 1 calc R . .
 C13 C 0.2791(7) 0.5404(2) -0.0694(8) 0.0322(12) Uani 1 1 d . . .
 H13A H 0.1685 0.5397 -0.1860 0.048 Uiso 1 1 calc R . .
 H13B H 0.3330 0.5060 -0.0430 0.048 Uiso 1 1 calc R . .
 H13C H 0.3630 0.5650 -0.0799 0.048 Uiso 1 1 calc R . .
 C6 C -0.0801(7) 0.5835(2) 0.3447(7) 0.0332(13) Uani 1 1 d . . .
 H6A H -0.1955 0.5701 0.2527 0.050 Uiso 1 1 calc R . .
 H6B H -0.0935 0.5978 0.4499 0.050 Uiso 1 1 calc R . .
 H6C H 0.0079 0.5555 0.3880 0.050 Uiso 1 1 calc R . .

loop_
  _atom_site_aniso_label
  _atom_site_aniso_U_11
  _atom_site_aniso_U_22
  _atom_site_aniso_U_33
  _atom_site_aniso_U_23
  _atom_site_aniso_U_13
  _atom_site_aniso_U_12
 Ir1 0.02148(11) 0.01573(10) 0.01488(9) -0.00173(8) 0.00698(7) -0.00303(8)
 Cl1 0.0245(6) 0.0233(6) 0.0254(6) -0.0041(5) 0.0024(5) -0.0054(5)
 Cl2 0.0580(9) 0.0246(7) 0.0285(7) -0.0021(5) 0.0283(6) -0.0065(6)
 C10 0.028(3) 0.033(3) 0.019(2) -0.004(2) 0.004(2) -0.005(2)
 N1 0.019(2) 0.021(2) 0.028(2) -0.0025(17) 0.0101(18) -0.0002(17)
 C2 0.027(3) 0.026(3) 0.019(2) -0.008(2) 0.012(2) -0.006(2)
 C12 0.022(3) 0.025(3) 0.035(3) 0.000(2) 0.005(2) 0.002(2)
 C5 0.032(3) 0.018(3) 0.023(3) -0.008(2) 0.016(2) -0.005(2)
 C3 0.023(3) 0.025(3) 0.025(3) -0.007(2) 0.010(2) 0.002(2)
 C4 0.034(3) 0.019(3) 0.025(3) -0.005(2) 0.016(2) 0.004(2)
 C1 0.028(3) 0.026(3) 0.015(2) -0.0096(19) 0.009(2) -0.006(2)
 C11 0.020(3) 0.038(3) 0.026(3) 0.002(2) -0.002(2) 0.000(2)
 C7 0.030(3) 0.045(4) 0.033(3) -0.003(3) 0.007(2) 0.001(3)
 C8 0.054(4) 0.023(3) 0.034(3) 0.003(2) 0.017(3) 0.007(3)
 C9 0.039(3) 0.025(3) 0.036(3) -0.014(2) 0.022(3) -0.014(2)
 C13 0.031(3) 0.032(3) 0.038(3) -0.005(2) 0.019(2) 0.003(2)
 C6 0.032(3) 0.045(3) 0.025(3) -0.004(2) 0.015(2) -0.016(3)

_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Ir1 Cl1 2.4451(12) . ?
 Ir1 Cl2 2.4361(12) . ?
 Ir1 N1 2.179(4) . ?
 Ir1 C2 2.166(5) . ?
 Ir1 C5 2.156(5) . ?
 Ir1 C3 2.188(5) . ?
 Ir1 C4 2.176(5) . ?
 Ir1 C1 2.161(4) . ?
 C10 C1 1.517(7) . ?
 C10 C11 1.555(7) . ?
 N1 C12 1.493(6) . ?
 N1 C13 1.497(6) . ?
 C2 C3 1.472(7) . ?
 C2 C1 1.468(7) . ?
 C2 C6 1.510(7) . ?
 C12 C11 1.530(8) . ?
 C5 C4 1.474(7) . ?
 C5 C1 1.445(7) . ?
 C5 C9 1.510(7) . ?
 C3 C4 1.428(7) . ?
 C3 C7 1.506(7) . ?
 C4 C8 1.508(7) . ?

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
 Cl2 Ir1 Cl1 90.14(4) . . ?
 N1 Ir1 Cl1 82.90(11) . . ?
 N1 Ir1 Cl2 89.38(11) . . ?
 N1 Ir1 C3 146.38(17) . . ?
 C2 Ir1 Cl1 103.70(13) . . ?
 C2 Ir1 Cl2 158.67(14) . . ?
 C2 Ir1 N1 108.16(17) . . ?
 C2 Ir1 C3 39.51(18) . . ?
 C2 Ir1 C4 66.10(19) . . ?
 C5 Ir1 Cl1 159.28(14) . . ?
 C5 Ir1 Cl2 94.99(13) . . ?
 C5 Ir1 N1 117.15(17) . . ?
 C5 Ir1 C2 66.51(18) . . ?
 C5 Ir1 C3 65.34(19) . . ?
 C5 Ir1 C4 39.78(19) . . ?
 C5 Ir1 C1 39.11(18) . . ?
 C3 Ir1 Cl1 95.26(13) . . ?
 C3 Ir1 Cl2 124.23(14) . . ?
 C4 Ir1 Cl1 120.02(14) . . ?
 C4 Ir1 Cl2 92.99(14) . . ?
 C4 Ir1 N1 156.92(17) . . ?
 C4 Ir1 C3 38.20(19) . . ?
 C1 Ir1 Cl1 140.71(13) . . ?
 C1 Ir1 Cl2 129.14(13) . . ?
 C1 Ir1 N1 95.14(17) . . ?
 C1 Ir1 C2 39.67(18) . . ?
 C1 Ir1 C3 65.39(18) . . ?
 C1 Ir1 C4 65.82(19) . . ?
 C1 C10 C11 115.6(4) . . ?
 C12 N1 Ir1 114.0(3) . . ?
 C12 N1 C13 110.1(4) . . ?
 C13 N1 Ir1 117.7(3) . . ?
 C3 C2 Ir1 71.0(3) . . ?
 C3 C2 C6 125.8(4) . . ?
 C1 C2 Ir1 70.0(2) . . ?
 C1 C2 C3 106.1(4) . . ?
 C1 C2 C6 127.5(5) . . ?
 C6 C2 Ir1 130.8(4) . . ?
 N1 C12 C11 114.2(4) . . ?
 C4 C5 Ir1 70.9(3) . . ?
 C4 C5 C9 124.9(4) . . ?
 C1 C5 Ir1 70.7(3) . . ?
 C1 C5 C4 107.7(4) . . ?
 C1 C5 C9 127.4(5) . . ?
 C9 C5 Ir1 126.7(3) . . ?
 C2 C3 Ir1 69.4(3) . . ?
 C2 C3 C7 124.3(5) . . ?
 C4 C3 Ir1 70.5(3) . . ?
 C4 C3 C2 109.5(4) . . ?
 C4 C3 C7 126.2(5) . . ?
 C7 C3 Ir1 125.5(4) . . ?
 C5 C4 Ir1 69.4(3) . . ?
 C5 C4 C8 125.3(5) . . ?
 C3 C4 Ir1 71.3(3) . . ?
 C3 C4 C5 107.8(4) . . ?
 C3 C4 C8 126.8(5) . . ?
 C8 C4 Ir1 127.2(4) . . ?
 C10 C1 Ir1 123.5(3) . . ?
 C2 C1 Ir1 70.3(2) . . ?
 C2 C1 C10 124.4(4) . . ?
 C5 C1 Ir1 70.2(3) . . ?
 C5 C1 C10 126.7(4) . . ?
 C5 C1 C2 108.9(4) . . ?
 C12 C11 C10 114.9(4) . . ?