#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:50:04 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195093 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/21/7042177.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_7042177
loop_
_publ_author_name
'Ou, Arnold'
'Wu, Linglin'
'Salvador, Alvaro'
'Sipos, Gellert'
'Zhao, Guangzhen'
'Skelton, Brian W.'
'Sobolev, Alexandre N.'
'Dorta, Reto'
_publ_section_title
;
 New, potentially chelating NHC ligands; synthesis, complexation studies,
 and preliminary catalytic evaluation.
;
_journal_issue                   11
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3631
_journal_page_last               3641
_journal_paper_doi               10.1039/c6dt04534k
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C35 H36 Cl Ir N4 O2'
_chemical_formula_sum            'C35 H36 Cl Ir N4 O2'
_chemical_formula_weight         772.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-24 deposited with the CCDC.
2017-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.255(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3082(2)
_cell_length_b                   14.41450(10)
_cell_length_c                   15.9946(2)
_cell_measurement_reflns_used    22566
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.883
_cell_measurement_theta_min      3.806
_cell_volume                     3094.82(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0111622000
_diffrn_orient_matrix_UB_12      0.0470572000
_diffrn_orient_matrix_UB_13      0.0054828000
_diffrn_orient_matrix_UB_21      -0.0400063000
_diffrn_orient_matrix_UB_22      -0.0143275000
_diffrn_orient_matrix_UB_23      0.0135305000
_diffrn_orient_matrix_UB_31      0.0326399000
_diffrn_orient_matrix_UB_32      -0.0014115000
_diffrn_orient_matrix_UB_33      0.0449758000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            53227
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.627
_diffrn_reflns_theta_min         3.683
_exptl_absorpt_coefficient_mu    4.439
_exptl_absorpt_correction_T_max  0.450
_exptl_absorpt_correction_T_min  0.292
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.225
_refine_diff_density_max         2.170
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         7986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+6.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7177
_reflns_number_total             7986
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt04534k2.cif
_cod_data_source_block           rda641
_cod_depositor_comments
'Adding full bibliography for 7042167--7042177.cif.'
_cod_database_code               7042177
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.259
_shelx_estimated_absorpt_t_max   0.435
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.2500 0.20847(2) 0.5000 0.02478(4) Uani 1 2 d S T P . .
Cl1 Cl 0.19883(13) 0.20486(10) 0.34194(17) 0.0343(3) Uani 0.5 1 d . . P . .
O12 O 0.3159(6) 0.1985(4) 0.6962(4) 0.0510(15) Uani 0.5 1 d . . P A 2
C12 C 0.2907(5) 0.2052(4) 0.6192(6) 0.0315(10) Uani 0.5 1 d . . P A 2
O11 O 0.2500 -0.0006(2) 0.5000 0.0516(8) Uani 1 2 d S T P . .
C11 C 0.2500 0.0758(2) 0.5000 0.0321(6) Uani 1 2 d S T P A .
C1 C 0.2500 0.3537(2) 0.5000 0.0343(7) Uani 1 2 d S T P A .
N2 N 0.33027(16) 0.40819(14) 0.53765(19) 0.0389(5) Uani 1 1 d . . . . .
C3 C 0.3068(2) 0.50800(18) 0.5158(3) 0.0598(11) Uani 1 1 d . . . . .
H3A H 0.3312 0.5290 0.4681 0.072 Uiso 1 1 calc R U . . .
H3B H 0.3357 0.5478 0.5689 0.072 Uiso 1 1 calc R U . . .
C21 C 0.43068(17) 0.37829(16) 0.57864(18) 0.0318(4) Uani 1 1 d . . . . .
C22 C 0.48174(17) 0.40233(16) 0.66729(18) 0.0304(4) Uani 1 1 d . . . . .
C23 C 0.58154(16) 0.37141(18) 0.70668(16) 0.0295(4) Uani 1 1 d . . . . .
H23 H 0.6172 0.3859 0.7673 0.035 Uiso 1 1 calc R U . . .
C24 C 0.62755(17) 0.32139(17) 0.65976(16) 0.0281(4) Uani 1 1 d . . . . .
H24 H 0.6933 0.2990 0.6890 0.034 Uiso 1 1 calc R U . . .
C24A C 0.57893(19) 0.30225(16) 0.56814(16) 0.0287(4) Uani 1 1 d . . . . .
C25 C 0.6289(2) 0.2579(2) 0.5170(2) 0.0394(6) Uani 1 1 d . . . . .
H25 H 0.6945 0.2349 0.5454 0.047 Uiso 1 1 calc R U . . .
C26 C 0.5838(3) 0.2480(3) 0.4270(2) 0.0511(8) Uani 1 1 d . . . . .
H26 H 0.6179 0.2178 0.3932 0.061 Uiso 1 1 calc R U . . .
C27 C 0.4877(3) 0.2820(3) 0.3846(2) 0.0531(9) Uani 1 1 d . . . . .
H27 H 0.4581 0.2772 0.3217 0.064 Uiso 1 1 calc R U . . .
C28A C 0.47913(18) 0.33304(16) 0.52637(16) 0.0299(4) Uani 1 1 d . . . . .
C28 C 0.4355(2) 0.3221(2) 0.43214(19) 0.0434(7) Uani 1 1 d . . . . .
H28 H 0.3694 0.3430 0.4021 0.052 Uiso 1 1 calc R U . . .
N221 N 0.43841(16) 0.45957(16) 0.7152(2) 0.0396(5) Uani 1 1 d . . . . .
C222 C 0.3563(2) 0.4206(2) 0.7388(3) 0.0445(7) Uani 1 1 d . . . . .
H22A H 0.3831 0.3778 0.7899 0.053 Uiso 1 1 calc R U . . .
H22B H 0.3115 0.3848 0.6877 0.053 Uiso 1 1 calc R U . . .
C223 C 0.2984(3) 0.4970(2) 0.7628(4) 0.0626(12) Uani 1 1 d . . . . .
H22C H 0.2445 0.4695 0.7804 0.075 Uiso 1 1 calc R U . . .
H22D H 0.2673 0.5369 0.7101 0.075 Uiso 1 1 calc R U . . .
C224 C 0.3651(3) 0.5553(3) 0.8385(4) 0.0693(14) Uani 1 1 d . . . . .
H22E H 0.3897 0.5176 0.8935 0.083 Uiso 1 1 calc R U . . .
H22F H 0.3268 0.6082 0.8496 0.083 Uiso 1 1 calc R U . . .
C225 C 0.4530(3) 0.5913(3) 0.8149(4) 0.0695(14) Uani 1 1 d . . . . .
H22G H 0.4288 0.6352 0.7644 0.083 Uiso 1 1 calc R U . . .
H22H H 0.4994 0.6252 0.8666 0.083 Uiso 1 1 calc R U . . .
C226 C 0.5078(2) 0.5115(3) 0.7899(3) 0.0561(10) Uani 1 1 d . . . . .
H22I H 0.5632 0.5361 0.7727 0.067 Uiso 1 1 calc R U . . .
H22J H 0.5363 0.4698 0.8417 0.067 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0991
0 -1 1 0.1697
0 -1 -1 0.1256
-2 1 4 0.1179
2 -1 -4 0.1441
-3 -1 3 0.1262
3 1 -3 0.1272
3 2 1 0.1173
-3 -3 1 0.1355
-1 5 -4 0.1338
-5 2 2 0.1797
-3 -2 -5 0.1903
4 -5 -2 0.1759
5 -2 -2 0.1666
2 5 0 0.1407
-2 -5 2 0.1571
0 -1 0 0.1369
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
C12 Ir1 C12 177.0(3) . 2_556
C12 Ir1 C11 88.49(17) . .
C12 Ir1 C11 88.49(17) 2_556 .
C12 Ir1 C1 91.51(17) . .
C12 Ir1 C1 91.51(17) 2_556 .
C11 Ir1 C1 180.0 . .
C12 Ir1 Cl1 177.08(18) . .
C11 Ir1 Cl1 88.74(4) . .
C1 Ir1 Cl1 91.26(4) . .
C12 Ir1 Cl1 177.08(18) 2_556 2_556
C11 Ir1 Cl1 88.74(4) . 2_556
C1 Ir1 Cl1 91.26(4) . 2_556
Cl1 Ir1 Cl1 177.49(7) . 2_556
O12 Cl1 C12 169.3(9) 2_556 2_556
O12 Cl1 Ir1 171.4(7) 2_556 .
Cl1 C12 Ir1 176.0(9) 2_556 .
O12 C12 Ir1 176.6(6) . .
O11 C11 Ir1 180.0 . .
N2 C1 N2 108.8(3) 2_556 .
N2 C1 Ir1 125.59(15) 2_556 .
N2 C1 Ir1 125.59(15) . .
C1 N2 C21 126.7(2) . .
C1 N2 C3 111.6(2) . .
C21 N2 C3 120.6(2) . .
N2 C3 C3 101.84(19) . 2_556
N2 C3 H3A 111.4 . .
C3 C3 H3A 111.4 2_556 .
N2 C3 H3B 111.4 . .
C3 C3 H3B 111.4 2_556 .
H3A C3 H3B 109.3 . .
C22 C21 C28A 121.5(2) . .
C22 C21 N2 118.8(2) . .
C28A C21 N2 119.3(2) . .
C21 C22 N221 121.6(2) . .
C21 C22 C23 117.8(2) . .
N221 C22 C23 120.5(2) . .
C24 C23 C22 121.7(2) . .
C24 C23 H23 119.1 . .
C22 C23 H23 119.1 . .
C23 C24 C24A 121.0(2) . .
C23 C24 H24 119.5 . .
C24A C24 H24 119.5 . .
C25 C24A C24 121.5(2) . .
C25 C24A C28A 119.8(2) . .
C24 C24A C28A 118.7(2) . .
C26 C25 C24A 120.6(3) . .
C26 C25 H25 119.7 . .
C24A C25 H25 119.7 . .
C25 C26 C27 120.1(3) . .
C25 C26 H26 119.9 . .
C27 C26 H26 119.9 . .
C28 C27 C26 121.0(3) . .
C28 C27 H27 119.5 . .
C26 C27 H27 119.5 . .
C21 C28A C24A 118.9(2) . .
C21 C28A C28 123.4(3) . .
C24A C28A C28 117.6(3) . .
C27 C28 C28A 120.8(3) . .
C27 C28 H28 119.6 . .
C28A C28 H28 119.6 . .
C22 N221 C222 117.3(2) . .
C22 N221 C226 116.1(2) . .
C222 N221 C226 111.4(3) . .
N221 C222 C223 110.3(2) . .
N221 C222 H22A 109.6 . .
C223 C222 H22A 109.6 . .
N221 C222 H22B 109.6 . .
C223 C222 H22B 109.6 . .
H22A C222 H22B 108.1 . .
C222 C223 C224 111.2(3) . .
C222 C223 H22C 109.4 . .
C224 C223 H22C 109.4 . .
C222 C223 H22D 109.4 . .
C224 C223 H22D 109.4 . .
H22C C223 H22D 108.0 . .
C223 C224 C225 109.7(4) . .
C223 C224 H22E 109.7 . .
C225 C224 H22E 109.7 . .
C223 C224 H22F 109.7 . .
C225 C224 H22F 109.7 . .
H22E C224 H22F 108.2 . .
C226 C225 C224 110.6(3) . .
C226 C225 H22G 109.5 . .
C224 C225 H22G 109.5 . .
C226 C225 H22H 109.5 . .
C224 C225 H22H 109.5 . .
H22G C225 H22H 108.1 . .
N221 C226 C225 109.6(3) . .
N221 C226 H22I 109.8 . .
C225 C226 H22I 109.8 . .
N221 C226 H22J 109.8 . .
C225 C226 H22J 109.8 . .
H22I C226 H22J 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C12 1.792(8) .
Ir1 C12 1.792(8) 2_556
Ir1 C11 1.912(4) .
Ir1 C1 2.094(3) .
Ir1 Cl1 2.377(2) .
Ir1 Cl1 2.377(2) 2_556
O12 C12 1.161(9) .
C12 Cl1 0.586(7) 2_556
O11 C11 1.102(4) .
C1 N2 1.349(3) 2_556
C1 N2 1.349(3) .
N2 C21 1.424(3) .
N2 C3 1.491(3) .
C3 C3 1.526(7) 2_556
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C21 C22 1.395(4) .
C21 C28A 1.416(4) .
C22 N221 1.408(3) .
C22 C23 1.418(3) .
C23 C24 1.363(3) .
C23 H23 0.9500 .
C24 C24A 1.415(3) .
C24 H24 0.9500 .
C24A C25 1.413(4) .
C24A C28A 1.422(4) .
C25 C26 1.366(4) .
C25 H25 0.9500 .
C26 C27 1.395(6) .
C26 H26 0.9500 .
C27 C28 1.364(6) .
C27 H27 0.9500 .
C28A C28 1.426(4) .
C28 H28 0.9500 .
N221 C222 1.465(4) .
N221 C226 1.467(4) .
C222 C223 1.505(4) .
C222 H22A 0.9900 .
C222 H22B 0.9900 .
C223 C224 1.512(6) .
C223 H22C 0.9900 .
C223 H22D 0.9900 .
C224 C225 1.524(5) .
C224 H22E 0.9900 .
C224 H22F 0.9900 .
C225 C226 1.522(5) .
C225 H22G 0.9900 .
C225 H22H 0.9900 .
C226 H22I 0.9900 .
C226 H22J 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3B N221 0.99 2.62 3.171(5) 115.1 .
C222 H22B Cl1 0.99 2.63 3.355(3) 129.9 2_556
C222 H22B N2 0.99 2.53 3.113(5) 117.5 .
C223 H22C Cl1 0.99 2.86 3.653(4) 138.0 8
C223 H22C O12 0.99 2.64 3.433(7) 137.0 7_556
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N2 C1 N2 C21 -175.2(4) 2_556 .
Ir1 C1 N2 C21 4.8(4) . .
N2 C1 N2 C3 -7.1(2) 2_556 .
Ir1 C1 N2 C3 172.9(2) . .
C1 N2 C3 C3 17.4(6) . 2_556
C21 N2 C3 C3 -173.7(4) . 2_556
C1 N2 C21 C22 -122.3(3) . .
C3 N2 C21 C22 70.6(4) . .
C1 N2 C21 C28A 63.8(4) . .
C3 N2 C21 C28A -103.3(4) . .
C28A C21 C22 N221 170.1(2) . .
N2 C21 C22 N221 -3.7(4) . .
C28A C21 C22 C23 -6.5(4) . .
N2 C21 C22 C23 179.8(2) . .
C21 C22 C23 C24 1.3(4) . .
N221 C22 C23 C24 -175.3(2) . .
C22 C23 C24 C24A 3.2(4) . .
C23 C24 C24A C25 174.1(3) . .
C23 C24 C24A C28A -2.5(4) . .
C24 C24A C25 C26 -173.8(3) . .
C28A C24A C25 C26 2.8(4) . .
C24A C25 C26 C27 0.3(5) . .
C25 C26 C27 C28 -2.8(6) . .
C22 C21 C28A C24A 7.2(3) . .
N2 C21 C28A C24A -179.1(2) . .
C22 C21 C28A C28 -168.3(2) . .
N2 C21 C28A C28 5.4(4) . .
C25 C24A C28A C21 -179.3(2) . .
C24 C24A C28A C21 -2.6(3) . .
C25 C24A C28A C28 -3.5(3) . .
C24 C24A C28A C28 173.2(2) . .
C26 C27 C28 C28A 2.0(5) . .
C21 C28A C28 C27 176.7(3) . .
C24A C28A C28 C27 1.1(4) . .
C21 C22 N221 C222 69.9(4) . .
C23 C22 N221 C222 -113.6(3) . .
C21 C22 N221 C226 -154.8(3) . .
C23 C22 N221 C226 21.7(4) . .
C22 N221 C222 C223 -162.2(3) . .
C226 N221 C222 C223 60.5(4) . .
N221 C222 C223 C224 -57.3(5) . .
C222 C223 C224 C225 54.5(5) . .
C223 C224 C225 C226 -54.6(6) . .
C22 N221 C226 C225 161.7(3) . .
C222 N221 C226 C225 -60.5(4) . .
C224 C225 C226 N221 57.4(6) . .
