#------------------------------------------------------------------------------
#$Date: 2020-04-04 08:04:40 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243339.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243339
loop_
_publ_author_name
'Bernier, Chad M.'
'DuChane, Christine M.'
'Merola, Joseph S.'
_publ_section_title
;
 Crystal structures of
 (η⁴-cycloocta-1,5-diene)bis(1,3-dimethylimidazol-2-ylidene)iridium(I)
 iodide and
 (η⁴-cycloocta-1,5-diene)bis(1,3-diethylimidazol-2-ylidene)iridium(I)
 iodide
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              611
_journal_page_last               614
_journal_paper_doi               10.1107/S2056989020004235
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          '[Ir (C5 H8 N2)2 (C8 H12)] I'
_chemical_formula_moiety         'C18 H28 Ir N4 +, I -'
_chemical_formula_sum            'C18 H28 I Ir N4'
_chemical_formula_weight         619.54
_chemical_name_systematic
;
(η⁴-Cycloocta-1,5-diene)bis(1,3-dimethylimidazol-2-ylidene)iridium(I) iodide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.241(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.6519(4)
_cell_length_b                   8.3070(2)
_cell_length_c                   9.7852(2)
_cell_measurement_reflns_used    17811
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      38.3310
_cell_measurement_theta_min      2.5940
_cell_volume                     2131.90(8)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27006
_diffrn_reflns_theta_full        36.500
_diffrn_reflns_theta_max         38.236
_diffrn_reflns_theta_min         3.107
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    7.718
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.179
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro;Rigaku OD, 2018)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_description       prism
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.537
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.107
_refine_diff_density_max         2.404
_refine_diff_density_min         -1.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         5884
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0317P)²+1.4859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0585
_reflns_number_gt                5415
_reflns_number_total             5884
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mw2156sup1.cif
_cod_data_source_block           1
_cod_database_code               2243339
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir1 0.35715(2) 0.500000 0.71082(2) 0.01615(3) Uani d 1 A .
N N1 0.36047(6) 0.6287(2) 0.41903(16) 0.0216(3) Uani d 1 . .
N N2 0.46647(6) 0.3712(2) 0.79484(18) 0.0242(3) Uani d 1 . .
C C1 0.36077(9) 0.500000 0.5047(2) 0.0184(4) Uani d 1 . .
C C2 0.36009(8) 0.5804(3) 0.28291(19) 0.0254(4) Uani d 1 . .
H H2 0.359874 0.648608 0.204874 0.031 Uiso calc 1 . .
C C3 0.36109(11) 0.7956(3) 0.4619(2) 0.0346(5) Uani d 1 . .
H H3A 0.394582 0.842411 0.458346 0.052 Uiso calc 1 . .
H H3B 0.354380 0.802066 0.557045 0.052 Uiso calc 1 . .
H H3C 0.334734 0.855247 0.399422 0.052 Uiso calc 1 . .
C C4 0.43494(9) 0.500000 0.7697(3) 0.0189(4) Uani d 1 . .
C C5 0.51693(8) 0.4201(3) 0.8329(2) 0.0336(5) Uani d 1 . .
H H5 0.545889 0.352001 0.854780 0.040 Uiso calc 1 . .
C C6 0.45066(10) 0.2032(3) 0.7875(3) 0.0353(5) Uani d 1 . .
H H6A 0.463915 0.149514 0.712161 0.053 Uiso calc 1 . .
H H6B 0.413344 0.197190 0.769749 0.053 Uiso calc 1 . .
H H6C 0.464082 0.149835 0.875787 0.053 Uiso calc 1 . .
C C7 0.27918(8) 0.4158(4) 0.6632(2) 0.0436(7) Uani d 1 . .
H H7A 0.268531 0.362122 0.571156 0.052 Uiso calc 0.485(19) A 1
H H7B 0.270988 0.372499 0.566457 0.052 Uiso calc 0.515(19) A 2
C C8 0.2597(3) 0.3445(15) 0.7821(6) 0.0346(18) Uani d 0.485(19) A 1
H H8A 0.237419 0.251494 0.749983 0.041 Uiso calc 0.485(19) A 1
H H8B 0.239134 0.425165 0.822295 0.041 Uiso calc 0.485(19) A 1
C C9 0.2980(3) 0.3377(15) 0.9218(8) 0.0330(18) Uani d 0.485(19) A 2
H H9A 0.274812 0.415708 0.955269 0.040 Uiso calc 0.485(19) A 2
H H9B 0.303203 0.246025 0.987461 0.040 Uiso calc 0.485(19) A 2
C C10 0.34831(8) 0.4171(3) 0.9159(2) 0.0329(5) Uani d 1 . .
H H10 0.380731 0.371865 0.969269 0.040 Uiso calc 0.485(19) A 1
H H10A 0.378957 0.364754 0.972248 0.040 Uiso calc 0.515(19) A 2
I I1 0.59789(2) 0.000000 0.87332(2) 0.03089(5) Uani d 1 . .
C C9A 0.3044(3) 0.2893(16) 0.8926(10) 0.0404(19) Uani d 0.515(19) A 1
H H9AA 0.317748 0.186061 0.863449 0.049 Uiso calc 0.515(19) A 1
H H9AB 0.292215 0.270733 0.981216 0.049 Uiso calc 0.515(19) A 1
C C8A 0.2740(4) 0.2775(14) 0.7760(6) 0.0386(18) Uani d 0.515(19) A 2
H H8AA 0.237614 0.251443 0.773250 0.046 Uiso calc 0.515(19) A 2
H H8AB 0.291638 0.178533 0.753713 0.046 Uiso calc 0.515(19) A 2
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'
I I -0.4742 1.8119 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 -4 0.1065
-5 0 4 0.1065
-5 1 5 0.0918
-5 0 -1 0.0508
5 -1 1 0.1159
5 0 2 0.0461
5 -1 3 0.0788
-2 -5 1 0.2115
-4 1 -5 0.0689
-1 0 0 0.0496
-2 -5 -5 0.2067
1 0 0 0.0622
5 2 -5 0.1065
2 1 5 0.0894
-31 3 -5 0.0872
36 3 -4 0.0795
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Ir1 C4 . . 93.14(10) ?
C1 Ir1 C7 . . 89.97(9) ?
C1 Ir1 C7 . 6_565 89.97(9) ?
C1 Ir1 C10 . . 161.15(8) ?
C1 Ir1 C10 . 6_565 161.16(8) ?
C4 Ir1 C7 . 6_565 160.90(9) ?
C4 Ir1 C7 . . 160.90(9) ?
C4 Ir1 C10 . . 90.61(8) ?
C4 Ir1 C10 . 6_565 90.61(8) ?
C7 Ir1 C7 6_565 . 37.71(19) ?
C7 Ir1 C10 . 6_565 92.50(9) ?
C7 Ir1 C10 6_565 . 92.49(9) ?
C7 Ir1 C10 6_565 6_565 80.72(8) ?
C7 Ir1 C10 . . 80.72(8) ?
C10 Ir1 C10 6_565 . 36.95(15) ?
C1 N1 C2 . . 111.26(18) ?
C1 N1 C3 . . 125.22(17) ?
C2 N1 C3 . . 123.51(18) ?
C4 N2 C5 . . 110.93(19) ?
C4 N2 C6 . . 125.66(17) ?
C5 N2 C6 . . 123.40(19) ?
N1 C1 Ir1 6_565 . 127.97(11) ?
N1 C1 Ir1 . . 127.97(11) ?
N1 C1 N1 . 6_565 103.9(2) ?
N1 C2 H2 . . 126.6 ?
C2 C2 N1 6_565 . 106.78(12) ?
C2 C2 H2 6_565 . 126.6 ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
N1 C3 H3C . . 109.5 ?
H3A C3 H3B . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N2 C4 Ir1 . . 127.89(11) ?
N2 C4 Ir1 6_565 . 127.89(11) ?
N2 C4 N2 6_565 . 104.2(2) ?
N2 C5 H5 . . 126.5 ?
C5 C5 N2 6_565 . 106.96(13) ?
C5 C5 H5 6_565 . 126.5 ?
N2 C6 H6A . . 109.5 ?
N2 C6 H6B . . 109.5 ?
N2 C6 H6C . . 109.5 ?
H6A C6 H6B . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
Ir1 C7 H7A . . 116.5 ?
Ir1 C7 H7B . . 111.1 ?
C7 C7 Ir1 6_565 . 71.14(10) ?
C7 C7 H7A 6_565 . 116.5 ?
C7 C7 H7B 6_565 . 111.1 ?
C7 C7 C8 6_565 . 113.6(5) ?
C7 C7 C8A 6_565 . 135.3(4) ?
C8 C7 Ir1 . . 114.8(3) ?
C8 C7 H7A . . 116.5 ?
C8A C7 Ir1 . . 106.1(3) ?
C8A C7 H7B . . 111.1 ?
C7 C8 H8A . . 109.7 ?
C7 C8 H8B . . 109.7 ?
C7 C8 C9A . . 109.7(5) ?
H8A C8 H8B . . 108.2 ?
C9A C8 H8A . . 109.7 ?
C9A C8 H8B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C10 C9 H9A . . 109.8 ?
C10 C9 H9B . . 109.8 ?
C10 C9 C8A . . 109.4(5) ?
C8A C9 H9A . . 109.8 ?
C8A C9 H9B . . 109.8 ?
Ir1 C10 H10 . . 112.1 ?
Ir1 C10 H10A . . 115.8 ?
C9 C10 Ir1 . . 114.7(3) ?
C9 C10 H10A . . 115.8 ?
C10 C10 Ir1 6_565 . 71.53(8) ?
C10 C10 C9 6_565 . 116.0(5) ?
C10 C10 H10 6_565 . 112.1 ?
C10 C10 H10A 6_565 . 115.8 ?
C10 C10 C9A 6_565 . 132.7(5) ?
C9A C10 Ir1 . . 106.3(4) ?
C9A C10 H10 . . 112.1 ?
C8 C9A C10 . . 111.6(7) ?
C8 C9A H9AA . . 109.3 ?
C8 C9A H9AB . . 109.3 ?
C10 C9A H9AA . . 109.3 ?
C10 C9A H9AB . . 109.3 ?
H9AA C9A H9AB . . 108.0 ?
C7 C8A H8AA . . 109.8 ?
C7 C8A H8AB . . 109.8 ?
C9 C8A C7 . . 109.3(6) ?
C9 C8A H8AA . . 109.8 ?
C9 C8A H8AB . . 109.8 ?
H8AA C8A H8AB . . 108.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 C1 . 2.037(2) ?
Ir1 C4 . 2.051(2) ?
Ir1 C7 6_565 2.163(2) ?
Ir1 C7 . 2.163(2) ?
Ir1 C10 6_565 2.174(2) ?
Ir1 C10 . 2.174(2) ?
N1 C1 . 1.357(2) ?
N1 C2 . 1.389(2) ?
N1 C3 . 1.448(3) ?
N2 C4 . 1.356(2) ?
N2 C5 . 1.391(3) ?
N2 C6 . 1.456(3) ?
C2 C2 6_565 1.336(5) ?
C2 H2 . 0.9500 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C5 C5 6_565 1.328(5) ?
C5 H5 . 0.9500 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C7 6_565 1.399(7) ?
C7 H7A . 1.0000 ?
C7 H7B . 1.0000 ?
C7 C8 . 1.480(6) ?
C7 C8A . 1.616(8) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C8 C9A . 1.530(12) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C9 C10 . 1.505(8) ?
C9 C8A . 1.540(10) ?
C10 C10 6_565 1.378(6) ?
C10 H10 . 1.0000 ?
C10 H10A . 1.0000 ?
C10 C9A . 1.567(10) ?
C9A H9AA . 0.9900 ?
C9A H9AB . 0.9900 ?
C8A H8AA . 0.9900 ?
C8A H8AB . 0.9900 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Ir1 C7 C8 C9A . . . . -21.8(8) ?
Ir1 C7 C8A C9 . . . . 46.8(7) ?
Ir1 C10 C9A C8 . . . . -43.0(7) ?
C1 N1 C2 C2 . . . 6_565 0.08(17) ?
C2 N1 C1 Ir1 . . . . -176.04(16) ?
C2 N1 C1 N1 . . . 6_565 -0.1(3) ?
C3 N1 C1 Ir1 . . . . 4.7(3) ?
C3 N1 C1 N1 . . . 6_565 -179.40(16) ?
C3 N1 C2 C2 . . . 6_565 179.37(17) ?
C4 N2 C5 C5 . . . 6_565 0.58(19) ?
C5 N2 C4 Ir1 . . . . -179.85(17) ?
C5 N2 C4 N2 . . . 6_565 -0.9(3) ?
C6 N2 C4 Ir1 . . . . -1.4(3) ?
C6 N2 C4 N2 . . . 6_565 177.51(16) ?
C6 N2 C5 C5 . . . 6_565 -177.88(18) ?
C7 C7 C8 C9A 6_565 . . . -101.0(6) ?
C7 C7 C8A C9 6_565 . . . -32.5(9) ?
C7 C8 C9A C10 . . . . 43.1(7) ?
C10 C9 C8A C7 . . . . -44.8(8) ?
C10 C10 C9A C8 6_565 . . . 36.7(8) ?
C8A C9 C10 Ir1 . . . . 21.6(8) ?
C8A C9 C10 C10 . . . 6_565 102.2(6) ?

_cod_database_fobs_code 2243339
