#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/45/4104579.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_4104579
loop_
_publ_author_name
'Ryohei Yamaguchi'
'Chikako Ikeda'
'Yoshinori Takahashi'
'Ken-ichi Fujita'
_publ_section_title
;
 Homogeneous Catalytic System for Reversible Dehydrogenation-Hydrogenation
 Reactions of Nitrogen Heterocycles with Reversible Interconversion of
 Catalytic Species
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8410
_journal_page_last               8412
_journal_paper_doi               10.1021/ja9022623
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C16 H18 Cl F3 Ir N O '
_chemical_formula_sum            'C16 H18 Cl F3 Ir N O'
_chemical_formula_weight         524.99
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.3380(14)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.4922(7)
_cell_length_b                   7.4836(3)
_cell_length_c                   18.1749(7)
_cell_measurement_reflns_used    12954
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1659.87(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    'DIRDIF99 (PATTY)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15131
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    8.259
_exptl_absorpt_correction_T_max  0.084
_exptl_absorpt_correction_T_min  0.083
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_description       block
_exptl_crystal_F_000             1000.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         2.74
_refine_diff_density_min         -2.66
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3028
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[1.0000σ(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0446
_reflns_number_gt                3028
_reflns_number_total             3763
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja9022623_si_001.cif
_cod_data_source_block           '_complex2c'
_cod_original_cell_volume        1659.86(13)
_cod_original_formula_sum        'C16 H18 Cl F3 Ir N O '
_cod_database_code               4104579
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,+Z
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
Ir(1) Ir 0.20457(2) 0.19786(3) 0.293820(10) 0.01871(7) Uani 1.00 1 d .
Cl(1) Cl 0.24521(12) 0.4889(2) 0.34500(7) 0.0305(3) Uani 1.00 1 d .
F(1) F 0.3911(3) 0.6716(5) 0.0556(2) 0.0499(13) Uani 1.00 1 d .
F(2) F 0.3170(3) 0.4923(6) -0.03106(18) 0.0601(13) Uani 1.00 1 d .
F(3) F 0.4442(3) 0.3976(6) 0.0593(2) 0.0573(13) Uani 1.00 1 d .
O(1) O 0.0614(3) 0.3280(4) 0.2187(2) 0.0265(10) Uani 1.00 1 d .
N(1) N 0.2237(4) 0.3122(5) 0.1914(2) 0.0215(12) Uani 1.00 1 d .
C(1) C 0.1457(5) -0.0721(7) 0.2946(3) 0.0295(15) Uani 1.00 1 d .
C(2) C 0.2520(4) -0.0723(7) 0.2798(2) 0.0240(14) Uani 1.00 1 d .
C(3) C 0.3248(4) 0.0078(7) 0.3448(2) 0.0227(14) Uani 1.00 1 d .
C(4) C 0.2584(5) 0.0527(7) 0.3983(2) 0.0315(16) Uani 1.00 1 d .
C(5) C 0.1494(4) 0.0092(7) 0.3671(3) 0.0274(15) Uani 1.00 1 d .
C(6) C 0.0463(5) -0.1451(9) 0.2413(4) 0.051(2) Uani 1.00 1 d .
C(7) C 0.2882(5) -0.1402(9) 0.2119(2) 0.0381(19) Uani 1.00 1 d .
C(8) C 0.4452(4) 0.0170(9) 0.3573(3) 0.0381(18) Uani 1.00 1 d .
C(9) C 0.3029(6) 0.1398(9) 0.4732(3) 0.046(2) Uani 1.00 1 d .
C(10) C 0.0564(5) 0.0245(10) 0.4051(3) 0.050(2) Uani 1.00 1 d .
C(11) C 0.1198(4) 0.3743(7) 0.1710(2) 0.0223(14) Uani 1.00 1 d .
C(12) C 0.0881(5) 0.4814(8) 0.1064(2) 0.0308(16) Uani 1.00 1 d .
C(13) C 0.1643(5) 0.5203(7) 0.0648(2) 0.0290(15) Uani 1.00 1 d .
C(14) C 0.2712(5) 0.4533(7) 0.0861(2) 0.0274(15) Uani 1.00 1 d .
C(15) C 0.2995(5) 0.3506(7) 0.1518(2) 0.0246(14) Uani 1.00 1 d .
C(16) C 0.3566(5) 0.5026(8) 0.0437(2) 0.0332(17) Uani 1.00 1 d .
H(1) H -0.0157 -0.1293 0.2632 0.058 Uiso 1.00 1 c R
H(2) H 0.0562 -0.2687 0.2330 0.059 Uiso 1.00 1 c R
H(3) H 0.0350 -0.0832 0.1946 0.058 Uiso 1.00 1 c R
H(4) H 0.2257 -0.1830 0.1771 0.045 Uiso 1.00 1 c R
H(5) H 0.3393 -0.2347 0.2255 0.046 Uiso 1.00 1 c R
H(6) H 0.3211 -0.0463 0.1894 0.046 Uiso 1.00 1 c R
H(7) H 0.4679 -0.0326 0.3150 0.045 Uiso 1.00 1 c R
H(8) H 0.4777 -0.0481 0.4013 0.045 Uiso 1.00 1 c R
H(9) H 0.4675 0.1384 0.3632 0.045 Uiso 1.00 1 c R
H(10) H 0.3802 0.1513 0.4799 0.056 Uiso 1.00 1 c R
H(11) H 0.2863 0.0671 0.5121 0.056 Uiso 1.00 1 c R
H(12) H 0.2712 0.2546 0.4750 0.056 Uiso 1.00 1 c R
H(13) H 0.0811 0.0788 0.4530 0.063 Uiso 1.00 1 c R
H(14) H 0.0274 -0.0905 0.4115 0.063 Uiso 1.00 1 c R
H(15) H 0.0010 0.0966 0.3754 0.063 Uiso 1.00 1 c R
H(16) H 0.0155 0.5262 0.0920 0.036 Uiso 1.00 1 c R
H(17) H 0.1455 0.5937 0.0214 0.033 Uiso 1.00 1 c R
H(18) H 0.3720 0.3065 0.1678 0.030 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ir Ir -1.444 7.990
;
International Tables for Crystallography
(1992, 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_publ_flag
Cl(1) Ir(1) O(1) 85.17(9) yes
Cl(1) Ir(1) N(1) 85.33(11) yes
Cl(1) Ir(1) C(1) 154.36(17) yes
Cl(1) Ir(1) C(2) 150.56(14) yes
Cl(1) Ir(1) C(3) 111.65(14) yes
Cl(1) Ir(1) C(4) 96.66(15) yes
Cl(1) Ir(1) C(5) 115.35(15) yes
O(1) Ir(1) N(1) 60.59(17) yes
O(1) Ir(1) C(1) 100.57(17) yes
O(1) Ir(1) C(2) 123.14(16) yes
O(1) Ir(1) C(3) 163.07(16) yes
O(1) Ir(1) C(4) 144.5(2) yes
O(1) Ir(1) C(5) 110.14(18) yes
N(1) Ir(1) C(1) 119.37(19) yes
N(1) Ir(1) C(2) 101.08(19) yes
N(1) Ir(1) C(3) 116.9(2) yes
N(1) Ir(1) C(4) 154.9(2) yes
N(1) Ir(1) C(5) 157.53(18) yes
C(1) Ir(1) C(2) 38.4(2) yes
C(1) Ir(1) C(3) 65.2(2) yes
C(1) Ir(1) C(4) 64.3(2) yes
C(1) Ir(1) C(5) 39.2(2) yes
C(2) Ir(1) C(3) 39.94(19) yes
C(2) Ir(1) C(4) 65.7(2) yes
C(2) Ir(1) C(5) 65.6(2) yes
C(3) Ir(1) C(4) 39.3(2) yes
C(3) Ir(1) C(5) 65.3(2) yes
C(4) Ir(1) C(5) 37.7(2) yes
Ir(1) O(1) C(11) 91.9(3) yes
Ir(1) N(1) C(11) 95.7(3) yes
Ir(1) N(1) C(15) 142.1(3) yes
C(11) N(1) C(15) 121.7(4) yes
Ir(1) C(1) C(2) 70.3(3) yes
Ir(1) C(1) C(5) 70.5(3) yes
Ir(1) C(1) C(6) 125.0(4) yes
C(2) C(1) C(5) 109.1(4) yes
C(2) C(1) C(6) 123.9(5) yes
C(5) C(1) C(6) 127.0(6) yes
Ir(1) C(2) C(1) 71.3(3) yes
Ir(1) C(2) C(3) 69.8(3) yes
Ir(1) C(2) C(7) 124.2(4) yes
C(1) C(2) C(3) 107.1(4) yes
C(1) C(2) C(7) 128.5(4) yes
C(3) C(2) C(7) 124.4(5) yes
Ir(1) C(3) C(2) 70.2(2) yes
Ir(1) C(3) C(4) 71.7(3) yes
Ir(1) C(3) C(8) 129.5(4) yes
C(2) C(3) C(4) 107.0(4) yes
C(2) C(3) C(8) 125.7(5) yes
C(4) C(3) C(8) 126.8(4) yes
Ir(1) C(4) C(3) 69.0(2) yes
Ir(1) C(4) C(5) 70.6(3) yes
Ir(1) C(4) C(9) 124.2(4) yes
C(3) C(4) C(5) 108.8(4) yes
C(3) C(4) C(9) 123.6(5) yes
C(5) C(4) C(9) 127.5(6) yes
Ir(1) C(5) C(1) 70.4(3) yes
Ir(1) C(5) C(4) 71.7(3) yes
Ir(1) C(5) C(10) 128.8(4) yes
C(1) C(5) C(4) 107.9(5) yes
C(1) C(5) C(10) 125.8(5) yes
C(4) C(5) C(10) 126.0(5) yes
O(1) C(11) N(1) 111.7(4) yes
O(1) C(11) C(12) 127.8(5) yes
N(1) C(11) C(12) 120.5(5) yes
C(11) C(12) C(13) 118.5(5) yes
C(12) C(13) C(14) 120.4(4) yes
C(13) C(14) C(15) 119.0(5) yes
C(13) C(14) C(16) 120.9(4) yes
C(15) C(14) C(16) 119.9(5) yes
N(1) C(15) C(14) 119.9(5) yes
F(1) C(16) F(2) 104.7(4) yes
F(1) C(16) F(3) 107.6(5) yes
F(1) C(16) C(14) 113.1(5) yes
F(2) C(16) F(3) 106.9(5) yes
F(2) C(16) C(14) 111.0(5) yes
F(3) C(16) C(14) 113.0(4) yes
C(1) C(6) H(1) 108.6 no
C(1) C(6) H(2) 109.7 no
C(1) C(6) H(3) 110.0 no
H(1) C(6) H(2) 109.5 no
H(1) C(6) H(3) 109.5 no
H(2) C(6) H(3) 109.5 no
C(2) C(7) H(4) 108.4 no
C(2) C(7) H(5) 110.2 no
C(2) C(7) H(6) 109.9 no
H(4) C(7) H(5) 109.5 no
H(4) C(7) H(6) 109.5 no
H(5) C(7) H(6) 109.5 no
C(3) C(8) H(7) 109.2 no
C(3) C(8) H(8) 110.1 no
C(3) C(8) H(9) 109.1 no
H(7) C(8) H(8) 109.5 no
H(7) C(8) H(9) 109.5 no
H(8) C(8) H(9) 109.5 no
C(4) C(9) H(10) 109.0 no
C(4) C(9) H(11) 109.2 no
C(4) C(9) H(12) 110.2 no
H(10) C(9) H(11) 109.5 no
H(10) C(9) H(12) 109.5 no
H(11) C(9) H(12) 109.5 no
C(5) C(10) H(13) 109.1 no
C(5) C(10) H(14) 110.2 no
C(5) C(10) H(15) 109.1 no
H(13) C(10) H(14) 109.5 no
H(13) C(10) H(15) 109.5 no
H(14) C(10) H(15) 109.5 no
C(11) C(12) H(16) 121.0 no
C(13) C(12) H(16) 120.6 no
C(12) C(13) H(17) 120.3 no
C(14) C(13) H(17) 119.3 no
N(1) C(15) H(18) 119.9 no
C(14) C(15) H(18) 120.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ir(1) Cl(1) 2.3799(15) yes
Ir(1) O(1) 2.229(3) yes
Ir(1) N(1) 2.108(4) yes
Ir(1) C(1) 2.151(5) yes
Ir(1) C(2) 2.137(5) yes
Ir(1) C(3) 2.131(5) yes
Ir(1) C(4) 2.166(5) yes
Ir(1) C(5) 2.152(6) yes
F(1) C(16) 1.338(7) yes
F(2) C(16) 1.345(5) yes
F(3) C(16) 1.328(8) yes
O(1) C(11) 1.293(7) yes
N(1) C(11) 1.353(7) yes
N(1) C(15) 1.339(8) yes
C(1) C(2) 1.410(8) yes
C(1) C(5) 1.443(8) yes
C(1) C(6) 1.504(8) yes
C(2) C(3) 1.458(6) yes
C(2) C(7) 1.492(8) yes
C(3) C(4) 1.445(8) yes
C(3) C(8) 1.474(8) yes
C(4) C(5) 1.397(8) yes
C(4) C(9) 1.505(7) yes
C(5) C(10) 1.478(9) yes
C(11) C(12) 1.406(7) yes
C(12) C(13) 1.368(9) yes
C(13) C(14) 1.401(8) yes
C(14) C(15) 1.400(7) yes
C(14) C(16) 1.490(9) yes
C(6) H(1) 0.950 no
C(6) H(2) 0.950 no
C(6) H(3) 0.950 no
C(7) H(4) 0.950 no
C(7) H(5) 0.950 no
C(7) H(6) 0.950 no
C(8) H(7) 0.950 no
C(8) H(8) 0.950 no
C(8) H(9) 0.950 no
C(9) H(10) 0.950 no
C(9) H(11) 0.950 no
C(9) H(12) 0.950 no
C(10) H(13) 0.950 no
C(10) H(14) 0.950 no
C(10) H(15) 0.950 no
C(12) H(16) 0.950 no
C(13) H(17) 0.950 no
C(15) H(18) 0.950 no
