data_2009src0359
 
#Dr. A. Marr
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H29 Cl2 Ir N2'
_chemical_formula_weight          536.53
 
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'
 '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    P2(1)/c
 
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                    13.2510(2)
_cell_length_b                    8.7390(2)
_cell_length_c                    17.9308(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  110.1450(10)
_cell_angle_gamma                 90.00
_cell_volume                      1949.37(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4657
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        'Cut Slab'
_exptl_crystal_colour             yellow
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.828
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1048
_exptl_absorpt_coefficient_mu     7.124
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.3299
_exptl_absorpt_correction_T_max   0.6745
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission: 0.5658 0.7456
The given Tmin and Tmax were generated using the SHELX SIZE command
;


_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             22487
_diffrn_reflns_av_R_equivalents   0.0430
_diffrn_reflns_av_sigmaI/netI     0.0407
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.31
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4469
_reflns_number_gt                 3984
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_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)+(0.0010P)²+1.4428P] 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          4469
_refine_ls_number_parameters      215
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0298
_refine_ls_R_factor_gt            0.0239
_refine_ls_wR_factor_ref          0.0470
_refine_ls_wR_factor_gt           0.0448
_refine_ls_goodness_of_fit_ref    1.105
_refine_ls_restrained_S_all       1.105
_refine_ls_shift/su_max           0.003
_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
Cl1 Cl 0.30885(6) 1.03064(9) 0.81001(6) 0.0317(2) Uani 1 1 d . . .
Cl2 Cl 0.20480(6) 0.89167(9) 0.93765(5) 0.02420(18) Uani 1 1 d . . .
Ir1 Ir 0.294994(8) 0.773717(13) 0.855843(7) 0.01458(5) Uani 1 1 d . . .
C1 C 0.1550(3) 0.7356(3) 0.7637(2) 0.0191(7) Uani 1 1 d . . .
C2 C -0.0092(3) 0.6443(4) 0.6894(2) 0.0296(8) Uani 1 1 d . . .
H2 H -0.0789 0.6009 0.6757 0.036 Uiso 1 1 calc R . .
C3 C 0.0382(3) 0.6928(5) 0.6396(2) 0.0358(9) Uani 1 1 d . . .
H3 H 0.0092 0.6884 0.5833 0.043 Uiso 1 1 calc R . .
C4 C 0.2151(3) 0.8059(6) 0.6491(2) 0.0446(11) Uani 1 1 d . . .
H4A H 0.2758 0.8546 0.6900 0.067 Uiso 1 1 calc R . .
H4B H 0.1801 0.8804 0.6074 0.067 Uiso 1 1 calc R . .
H4C H 0.2412 0.7193 0.6261 0.067 Uiso 1 1 calc R . .
C5 C 0.0387(2) 0.6255(4) 0.8357(2) 0.0234(7) Uani 1 1 d . . .
H5A H 0.1031 0.6417 0.8835 0.028 Uiso 1 1 calc R . .
H5B H 0.0205 0.5152 0.8326 0.028 Uiso 1 1 calc R . .
C6 C -0.0540(3) 0.7170(4) 0.8435(2) 0.0244(8) Uani 1 1 d . . .
H6A H -0.1216 0.6839 0.8019 0.029 Uiso 1 1 calc R . .
H6B H -0.0430 0.8267 0.8347 0.029 Uiso 1 1 calc R . .
C7 C -0.0647(3) 0.6972(5) 0.9247(2) 0.0383(10) Uani 1 1 d . . .
H7A H -0.0727 0.5870 0.9343 0.046 Uiso 1 1 calc R . .
H7B H 0.0018 0.7339 0.9660 0.046 Uiso 1 1 calc R . .
C8 C -0.1602(3) 0.7836(5) 0.9324(2) 0.0425(11) Uani 1 1 d . . .
H8A H -0.1515 0.8932 0.9249 0.064 Uiso 1 1 calc R . .
H8B H -0.1641 0.7660 0.9852 0.064 Uiso 1 1 calc R . .
H8C H -0.2264 0.7472 0.8918 0.064 Uiso 1 1 calc R . .
N1 N 0.06284(19) 0.6695(3) 0.76533(16) 0.0203(6) Uani 1 1 d . . .
N2 N 0.1380(2) 0.7511(3) 0.68473(18) 0.0288(7) Uani 1 1 d . . .
C11 C 0.3579(2) 0.5554(3) 0.8390(2) 0.0190(7) Uani 1 1 d . . .
C12 C 0.3467(2) 0.5600(3) 0.9159(2) 0.0192(7) Uani 1 1 d . . .
C13 C 0.4225(2) 0.6746(4) 0.96317(18) 0.0171(7) Uani 1 1 d . . .
C14 C 0.4728(2) 0.7445(3) 0.9145(2) 0.0185(7) Uani 1 1 d . . .
C15 C 0.4326(2) 0.6728(4) 0.8364(2) 0.0205(7) Uani 1 1 d . . .
C16 C 0.3041(3) 0.4432(4) 0.7740(2) 0.0320(9) Uani 1 1 d . . .
H16A H 0.3003 0.4865 0.7227 0.048 Uiso 1 1 calc R . .
H16B H 0.2313 0.4218 0.7735 0.048 Uiso 1 1 calc R . .
H16C H 0.3457 0.3479 0.7834 0.048 Uiso 1 1 calc R . .
C17 C 0.2847(3) 0.4502(4) 0.9478(2) 0.0329(9) Uani 1 1 d . . .
H17A H 0.2264 0.4048 0.9035 0.049 Uiso 1 1 calc R . .
H17B H 0.2544 0.5048 0.9829 0.049 Uiso 1 1 calc R . .
H17C H 0.3328 0.3691 0.9777 0.049 Uiso 1 1 calc R . .
C18 C 0.4390(3) 0.7082(4) 1.0487(2) 0.0266(8) Uani 1 1 d . . .
H18A H 0.5029 0.7725 1.0712 0.040 Uiso 1 1 calc R . .
H18B H 0.4489 0.6120 1.0785 0.040 Uiso 1 1 calc R . .
H18C H 0.3760 0.7620 1.0523 0.040 Uiso 1 1 calc R . .
C19 C 0.5543(2) 0.8710(4) 0.9359(2) 0.0263(8) Uani 1 1 d . . .
H19A H 0.5703 0.8998 0.9916 0.039 Uiso 1 1 calc R . .
H19B H 0.5256 0.9598 0.9018 0.039 Uiso 1 1 calc R . .
H19C H 0.6203 0.8360 0.9282 0.039 Uiso 1 1 calc R . .
C20 C 0.4778(3) 0.7014(4) 0.7717(2) 0.0311(8) Uani 1 1 d . . .
H20A H 0.5502 0.6578 0.7870 0.047 Uiso 1 1 calc R . .
H20B H 0.4812 0.8118 0.7635 0.047 Uiso 1 1 calc R . .
H20C H 0.4315 0.6533 0.7225 0.047 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
Cl1 Ir1 2.4196(8) . ?
Cl2 Ir1 2.4188(8) . ?
Ir1 C1 2.042(3) . ?
Ir1 C11 2.144(3) . ?
Ir1 C12 2.147(3) . ?
Ir1 C15 2.159(3) . ?
Ir1 C14 2.239(3) . ?
Ir1 C13 2.252(3) . ?
C1 N1 1.361(4) . ?
C1 N2 1.362(4) . ?
C2 C3 1.326(5) . ?
C2 N1 1.385(4) . ?
C2 H2 0.9500 . ?
C3 N2 1.388(5) . ?
C3 H3 0.9500 . ?
C4 N2 1.459(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.456(4) . ?
C5 C6 1.512(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.521(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.519(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C12 1.436(5) . ?
C11 C15 1.438(4) . ?
C11 C16 1.503(4) . ?
C12 C13 1.464(4) . ?
C12 C17 1.498(4) . ?
C13 C14 1.407(5) . ?
C13 C18 1.502(5) . ?
C14 C15 1.457(5) . ?
C14 C19 1.500(4) . ?
C15 C20 1.498(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
 
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 C11 91.71(12) . . ?
C1 Ir1 C12 107.93(12) . . ?
C11 Ir1 C12 39.11(12) . . ?
C1 Ir1 C15 112.65(13) . . ?
C11 Ir1 C15 39.04(12) . . ?
C12 Ir1 C15 65.43(12) . . ?
C1 Ir1 C14 151.28(13) . . ?
C11 Ir1 C14 64.39(11) . . ?
C12 Ir1 C14 64.09(11) . . ?
C15 Ir1 C14 38.64(12) . . ?
C1 Ir1 C13 146.50(12) . . ?
C11 Ir1 C13 64.16(12) . . ?
C12 Ir1 C13 38.80(11) . . ?
C15 Ir1 C13 63.51(12) . . ?
C14 Ir1 C13 36.52(12) . . ?
C1 Ir1 Cl2 93.40(9) . . ?
C11 Ir1 Cl2 139.59(9) . . ?
C12 Ir1 Cl2 101.86(9) . . ?
C15 Ir1 Cl2 153.26(9) . . ?
C14 Ir1 Cl2 115.04(9) . . ?
C13 Ir1 Cl2 91.58(8) . . ?
C1 Ir1 Cl1 91.75(9) . . ?
C11 Ir1 Cl1 134.38(9) . . ?
C12 Ir1 Cl1 158.32(8) . . ?
C15 Ir1 Cl1 99.05(9) . . ?
C14 Ir1 Cl1 94.28(8) . . ?
C13 Ir1 Cl1 121.67(8) . . ?
Cl2 Ir1 Cl1 85.51(3) . . ?
N1 C1 N2 103.7(3) . . ?
N1 C1 Ir1 128.6(2) . . ?
N2 C1 Ir1 127.1(2) . . ?
C3 C2 N1 106.6(3) . . ?
C3 C2 H2 126.7 . . ?
N1 C2 H2 126.7 . . ?
C2 C3 N2 107.6(3) . . ?
C2 C3 H3 126.2 . . ?
N2 C3 H3 126.2 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 111.6(3) . . ?
N1 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 112.0(3) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 112.6(3) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 C2 111.5(3) . . ?
C1 N1 C5 126.7(3) . . ?
C2 N1 C5 121.8(3) . . ?
C1 N2 C3 110.7(3) . . ?
C1 N2 C4 126.7(3) . . ?
C3 N2 C4 122.4(3) . . ?
C12 C11 C15 108.1(3) . . ?
C12 C11 C16 125.8(3) . . ?
C15 C11 C16 126.0(3) . . ?
C12 C11 Ir1 70.54(17) . . ?
C15 C11 Ir1 71.06(17) . . ?
C16 C11 Ir1 125.9(2) . . ?
C11 C12 C13 107.3(3) . . ?
C11 C12 C17 126.8(3) . . ?
C13 C12 C17 125.0(3) . . ?
C11 C12 Ir1 70.34(17) . . ?
C13 C12 Ir1 74.48(17) . . ?
C17 C12 Ir1 128.8(2) . . ?
C14 C13 C12 108.4(3) . . ?
C14 C13 C18 127.9(3) . . ?
C12 C13 C18 123.7(3) . . ?
C14 C13 Ir1 71.27(17) . . ?
C12 C13 Ir1 66.73(16) . . ?
C18 C13 Ir1 126.9(2) . . ?
C13 C14 C15 108.3(3) . . ?
C13 C14 C19 127.9(3) . . ?
C15 C14 C19 123.7(3) . . ?
C13 C14 Ir1 72.21(17) . . ?
C15 C14 Ir1 67.71(17) . . ?
C19 C14 Ir1 125.8(2) . . ?
C11 C15 C14 107.7(3) . . ?
C11 C15 C20 127.4(3) . . ?
C14 C15 C20 124.1(3) . . ?
C11 C15 Ir1 69.91(17) . . ?
C14 C15 Ir1 73.65(17) . . ?
C20 C15 Ir1 129.9(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.833
_refine_diff_density_min   -1.040
_refine_diff_density_rms    0.131
