#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/03/1520372.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520372
loop_
_publ_author_name
'Marr, Andrew'
'Penn-Kook, Annie'
'Lacroix, Sophie'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C18H29N2Cl2Ir
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              701
_journal_year                    2009
_chemical_formula_sum            'C18 H29 Cl2 Ir N2'
_chemical_formula_weight         536.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.1450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2510(2)
_cell_length_b                   8.7390(2)
_cell_length_c                   17.9308(4)
_cell_measurement_reflns_used    4657
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1949.37(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22487
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    7.124
_exptl_absorpt_correction_T_max  0.6745
_exptl_absorpt_correction_T_min  0.3299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut Slab'
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.833
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0010P)²+1.4428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0448
_refine_ls_wR_factor_ref         0.0470
_reflns_number_gt                3984
_reflns_number_total             4469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-701.cif
_cod_data_source_block           2009src0359
_cod_depositor_comments
;
Citation :
Marr, Andrew and Penn-Kook, Annie and Lacroix, Sophie and 
Horton, Peter N. and Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/701)

More at:
http://ecrystals.chem.soton.ac.uk/701/
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1520372
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'
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 . .
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'
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
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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 .
