data_rob250_0m
_audit_creation_date              2013-04-10
_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          'C12 H20 Cl2 Ir N'
_chemical_formula_sum             'C12 H20 Cl2 Ir N'
_chemical_formula_weight          441.39
_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/n 1'
_space_group_name_Hall            '-P 2yn'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x+1/2, y+1/2, -z+1/2'
 3 '-x, -y, -z'
 4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                    8.2714(5)
_cell_length_b                    9.2670(5)
_cell_length_c                    18.7176(12)
_cell_angle_alpha                 90.00
_cell_angle_beta                  98.855(3)
_cell_angle_gamma                 90.00
_cell_volume                      1417.62(15)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     7116
_cell_measurement_temperature     110(2)
_cell_measurement_theta_max       30.27
_cell_measurement_theta_min       2.46
_exptl_absorpt_coefficient_mu     9.770
_exptl_absorpt_correction_T_max   0.7461
_exptl_absorpt_correction_T_min   0.4752
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0846 before and 0.0307 after correction.
The Ratio of minimum to maximum transmission is 0.6369.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour             orange
_exptl_crystal_colour_primary     orange
_exptl_crystal_density_diffrn     2.068
_exptl_crystal_density_meas       .
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        block
_exptl_crystal_F_000              840
_exptl_crystal_size_max           0.31
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.26
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0213
_diffrn_reflns_av_unetI/netI      0.0243
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_l_max        26
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_number             11339
_diffrn_reflns_theta_full         30.29
_diffrn_reflns_theta_max          30.29
_diffrn_reflns_theta_min          2.56
_diffrn_ambient_temperature       110(2)
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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                 3887
_reflns_number_total              4205
_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          2.948
_refine_diff_density_min          -1.792
_refine_diff_density_rms          0.151
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_hydrogen_treatment     riding
_refine_ls_matrix_type            full
_refine_ls_number_parameters      149
_refine_ls_number_reflns          4205
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0259
_refine_ls_R_factor_gt            0.0230
_refine_ls_restrained_S_all       1.034
_refine_ls_shift/su_max           0.002
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0210P)^2^+4.5792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.0518
_refine_ls_wR_factor_ref          0.0529
_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:
  {H2A,H2B} of C2, {H1C,H1D} of C1, {H3A,H3B} of C3, {H1A,H1B} of N1
 At 1.5 times of:
  {H8A,H8B,H8C} of C8, {H12A,H12B,H12C} of C12, {H10A,H10B,H10C} of C10, {H6A,
  H6B,H6C} of C6
2.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C10(H10A,H10B,H10C)
;
_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 0.567358(13) 0.313697(13) 0.381972(6) 0.01294(4) Uani 1 1 d . . .
 C4 C 0.7566(4) 0.1602(3) 0.37294(17) 0.0153(6) Uani 1 1 d . . .
 Cl1 Cl 0.30245(10) 0.31297(11) 0.42279(6) 0.0306(2) Uani 1 1 d . . .
 Cl2 Cl 0.55035(12) 0.57417(9) 0.36332(5) 0.02908(19) Uani 1 1 d . . .
 N1 N 0.6559(3) 0.3716(3) 0.49158(16) 0.0205(6) Uani 1 1 d . . .
 H1A H 0.6847 0.4675 0.4920 0.025 Uiso 1 1 calc R . .
 H1B H 0.5697 0.3638 0.5171 0.025 Uiso 1 1 calc R . .
 C7 C 0.5930(4) 0.2592(4) 0.27012(18) 0.0176(6) Uani 1 1 d . . .
 C5 C 0.7524(4) 0.2674(4) 0.31581(17) 0.0156(6) Uani 1 1 d . . .
 C9 C 0.4994(4) 0.1493(4) 0.2994(2) 0.0209(7) Uani 1 1 d . . .
 C1 C 0.7972(5) 0.2905(5) 0.5327(2) 0.0288(8) Uani 1 1 d . . .
 H1C H 0.7578 0.1964 0.5482 0.035 Uiso 1 1 calc R . .
 H1D H 0.8413 0.3456 0.5767 0.035 Uiso 1 1 calc R . .
 C2 C 0.9339(5) 0.2644(5) 0.4883(2) 0.0312(9) Uani 1 1 d . . .
 H2A H 1.0362 0.2439 0.5217 0.037 Uiso 1 1 calc R . .
 H2B H 0.9513 0.3539 0.4616 0.037 Uiso 1 1 calc R . .
 C3 C 0.8999(5) 0.1365(4) 0.4327(2) 0.0258(8) Uani 1 1 d . . .
 H3A H 0.9994 0.1201 0.4104 0.031 Uiso 1 1 calc R . .
 H3B H 0.8796 0.0478 0.4593 0.031 Uiso 1 1 calc R . .
 C11 C 0.5994(4) 0.0879(3) 0.3636(2) 0.0197(7) Uani 1 1 d . . .
 C6 C 0.8912(5) 0.3621(5) 0.2997(2) 0.0268(8) Uani 1 1 d . . .
 H6A H 0.8527 0.4620 0.2929 0.040 Uiso 1 1 calc R . .
 H6B H 0.9293 0.3281 0.2556 0.040 Uiso 1 1 calc R . .
 H6C H 0.9814 0.3578 0.3403 0.040 Uiso 1 1 calc R . .
 C8 C 0.5434(6) 0.3502(5) 0.2038(2) 0.0320(9) Uani 1 1 d . . .
 H8A H 0.4242 0.3477 0.1905 0.048 Uiso 1 1 calc R . .
 H8B H 0.5947 0.3122 0.1639 0.048 Uiso 1 1 calc R . .
 H8C H 0.5792 0.4499 0.2140 0.048 Uiso 1 1 calc R . .
 C12 C 0.5513(7) -0.0391(4) 0.4069(3) 0.0407(11) Uani 1 1 d . . .
 H12A H 0.6206 -0.0409 0.4544 0.061 Uiso 1 1 calc R . .
 H12B H 0.5658 -0.1290 0.3811 0.061 Uiso 1 1 calc R . .
 H12C H 0.4365 -0.0293 0.4134 0.061 Uiso 1 1 calc R . .
 C10 C 0.3268(5) 0.1054(5) 0.2689(3) 0.0380(11) Uani 1 1 d . . .
 H10A H 0.2679 0.0784 0.3085 0.057 Uiso 1 1 calc R . .
 H10B H 0.3298 0.0228 0.2364 0.057 Uiso 1 1 calc R . .
 H10C H 0.2707 0.1863 0.2419 0.057 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 0.01059(6) 0.01020(6) 0.01764(6) -0.00480(4) 0.00092(4) 0.00096(4)
 C4 0.0184(14) 0.0123(14) 0.0167(14) 0.0010(11) 0.0081(11) 0.0054(11)
 Cl1 0.0137(3) 0.0401(5) 0.0391(5) -0.0248(4) 0.0080(3) -0.0044(3)
 Cl2 0.0437(5) 0.0120(4) 0.0304(4) -0.0018(3) 0.0020(4) 0.0085(4)
 N1 0.0168(12) 0.0216(15) 0.0217(14) -0.0074(12) -0.0019(10) 0.0059(11)
 C7 0.0180(14) 0.0191(15) 0.0150(14) -0.0047(12) 0.0002(11) 0.0024(12)
 C5 0.0151(13) 0.0170(15) 0.0147(14) 0.0018(12) 0.0024(11) 0.0003(12)
 C9 0.0184(14) 0.0176(15) 0.0285(18) -0.0143(14) 0.0088(13) -0.0036(13)
 C1 0.0264(17) 0.036(2) 0.0223(17) -0.0011(16) -0.0033(14) 0.0078(16)
 C2 0.0236(17) 0.046(2) 0.0232(18) 0.0016(17) 0.0014(14) 0.0078(18)
 C3 0.0267(17) 0.0291(19) 0.0210(17) 0.0029(14) 0.0024(13) 0.0157(15)
 C11 0.0275(16) 0.0079(13) 0.0279(17) -0.0047(12) 0.0175(14) -0.0072(12)
 C6 0.0260(17) 0.034(2) 0.0219(17) 0.0034(15) 0.0102(14) -0.0101(16)
 C8 0.041(2) 0.032(2) 0.0199(17) 0.0011(16) -0.0061(16) 0.0087(18)
 C12 0.075(3) 0.0163(18) 0.039(2) -0.0059(17) 0.035(2) -0.013(2)
 C10 0.0204(16) 0.044(3) 0.051(3) -0.031(2) 0.0082(17) -0.0099(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
 Ir1 C4 2.141(3) . ?
 Ir1 Cl1 2.4291(8) . ?
 Ir1 Cl2 2.4398(9) . ?
 Ir1 N1 2.138(3) . ?
 Ir1 C7 2.195(3) . ?
 Ir1 C5 2.155(3) . ?
 Ir1 C9 2.181(3) . ?
 Ir1 C11 2.144(3) . ?
 C4 C5 1.456(4) . ?
 C4 C3 1.515(5) . ?
 C4 C11 1.450(5) . ?
 N1 C1 1.499(5) . ?
 C7 C5 1.459(4) . ?
 C7 C9 1.438(5) . ?
 C7 C8 1.504(5) . ?
 C5 C6 1.512(5) . ?
 C9 C11 1.465(5) . ?
 C9 C10 1.509(5) . ?
 C1 C2 1.521(6) . ?
 C2 C3 1.575(6) . ?
 C11 C12 1.517(5) . ?

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
 C4 Ir1 Cl1 136.80(9) . . ?
 C4 Ir1 Cl2 132.27(9) . . ?
 C4 Ir1 C7 65.96(12) . . ?
 C4 Ir1 C5 39.61(12) . . ?
 C4 Ir1 C9 65.93(13) . . ?
 C4 Ir1 C11 39.54(13) . . ?
 Cl1 Ir1 Cl2 90.73(4) . . ?
 N1 Ir1 C4 95.50(12) . . ?
 N1 Ir1 Cl1 83.75(8) . . ?
 N1 Ir1 Cl2 83.85(9) . . ?
 N1 Ir1 C7 154.65(12) . . ?
 N1 Ir1 C5 115.65(11) . . ?
 N1 Ir1 C9 150.23(14) . . ?
 N1 Ir1 C11 111.50(13) . . ?
 C7 Ir1 Cl1 121.58(9) . . ?
 C7 Ir1 Cl2 95.92(10) . . ?
 C5 Ir1 Cl1 159.24(9) . . ?
 C5 Ir1 Cl2 98.35(9) . . ?
 C5 Ir1 C7 39.17(12) . . ?
 C5 Ir1 C9 65.31(12) . . ?
 C9 Ir1 Cl1 94.25(9) . . ?
 C9 Ir1 Cl2 125.92(11) . . ?
 C9 Ir1 C7 38.37(13) . . ?
 C11 Ir1 Cl1 100.82(9) . . ?
 C11 Ir1 Cl2 161.53(10) . . ?
 C11 Ir1 C7 65.77(13) . . ?
 C11 Ir1 C5 66.22(12) . . ?
 C11 Ir1 C9 39.58(14) . . ?
 C5 C4 Ir1 70.71(18) . . ?
 C5 C4 C3 124.7(3) . . ?
 C3 C4 Ir1 122.4(2) . . ?
 C11 C4 Ir1 70.34(18) . . ?
 C11 C4 C5 107.9(3) . . ?
 C11 C4 C3 127.4(3) . . ?
 C1 N1 Ir1 119.4(2) . . ?
 C5 C7 Ir1 68.92(18) . . ?
 C5 C7 C8 124.2(3) . . ?
 C9 C7 Ir1 70.27(19) . . ?
 C9 C7 C5 107.7(3) . . ?
 C9 C7 C8 128.1(3) . . ?
 C8 C7 Ir1 127.1(3) . . ?
 C4 C5 Ir1 69.68(17) . . ?
 C4 C5 C7 108.2(3) . . ?
 C4 C5 C6 127.5(3) . . ?
 C7 C5 Ir1 71.91(18) . . ?
 C7 C5 C6 124.0(3) . . ?
 C6 C5 Ir1 128.8(3) . . ?
 C7 C9 Ir1 71.37(19) . . ?
 C7 C9 C11 108.6(3) . . ?
 C7 C9 C10 125.5(4) . . ?
 C11 C9 Ir1 68.86(18) . . ?
 C11 C9 C10 126.0(4) . . ?
 C10 C9 Ir1 125.6(2) . . ?
 N1 C1 C2 112.7(3) . . ?
 C1 C2 C3 114.1(4) . . ?
 C4 C3 C2 114.8(3) . . ?
 C4 C11 Ir1 70.11(18) . . ?
 C4 C11 C9 107.6(3) . . ?
 C4 C11 C12 126.7(4) . . ?
 C9 C11 Ir1 71.56(19) . . ?
 C9 C11 C12 125.4(3) . . ?
 C12 C11 Ir1 128.4(3) . . ?