#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:52:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178671 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/82/4078241.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_4078241
loop_
_publ_author_name
'Azua, Arturo'
'Mata, Jose A.'
'Peris, Eduardo'
'Lamaty, Frederic'
'Martinez, Jean'
'Colacino, Evelina'
_publ_section_title
;
 Alternative Energy Input for Transfer Hydrogenation using Iridium NHC
 Based Catalysts in Glycerol as Hydrogen Donor and Solvent
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              3911
_journal_paper_doi               10.1021/om300109e
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C33 H43 Cl2 Ir N2 O6'
_chemical_formula_sum            'C33 H43 Cl2 Ir N2 O6'
_chemical_formula_weight         826.79
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-11-26
_audit_creation_method
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.610(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8446(9)
_cell_length_b                   28.210(2)
_cell_length_c                   8.2365(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1657.1(4)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_av_unetI/netI     0.1114
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14723
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.81
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    4.236
_exptl_absorpt_correction_T_max  0.759
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.876
_refine_diff_density_min         -1.231
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                2702
_reflns_number_total             3811
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300109e_si_004.cif
_cod_data_source_block           str1232_complex_5A
_cod_original_cell_volume        1657.1(3)
_cod_database_code               4078241
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
3 '-x, -y, -z'
4 'x, -y-1/2, 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
Ir1 Ir 0.36026(7) 0.2500 0.96130(6) 0.03681(18) Uani 1 2 d S
N4 N 0.1883(9) 0.2878(2) 0.5747(9) 0.0362(16) Uani 1 1 d .
C21 C 0.5826(12) 0.2746(3) 1.2149(12) 0.047(2) Uani 1 1 d .
C20 C 0.6151(11) 0.2907(3) 1.0625(11) 0.043(2) Uani 1 1 d .
C19 C 0.6363(16) 0.2500 0.9737(17) 0.047(3) Uani 1 2 d S
C23 C 0.6490(13) 0.3413(3) 1.0303(13) 0.062(3) Uani 1 1 d .
H23A H 0.7679 0.3514 1.1198 0.093 Uiso 1 1 calc R
H23B H 0.5513 0.3608 1.0361 0.093 Uiso 1 1 calc R
H23C H 0.6494 0.3443 0.9144 0.093 Uiso 1 1 calc R
C22 C 0.6852(17) 0.2500 0.8143(17) 0.054(3) Uani 1 2 d S
H22A H 0.6061 0.2721 0.7268 0.081 Uiso 0.50 1 calc PR
H22B H 0.6664 0.2188 0.7631 0.081 Uiso 0.50 1 calc PR
H22C H 0.8140 0.2590 0.8518 0.081 Uiso 0.50 1 calc PR
C3 C 0.2313(15) 0.2500 0.6862(15) 0.035(3) Uani 1 2 d S
C5 C 0.1184(11) 0.2738(3) 0.3978(12) 0.043(2) Uani 1 1 d .
H5 H 0.0792 0.2935 0.2983 0.052 Uiso 1 1 calc R
C6 C 0.2494(12) 0.3372(3) 0.6322(12) 0.043(2) Uani 1 1 d .
H6A H 0.3690 0.3427 0.6269 0.051 Uiso 1 1 calc R
H6B H 0.2675 0.3410 0.7553 0.051 Uiso 1 1 calc R
C7 C 0.1091(12) 0.3741(3) 0.5175(12) 0.044(2) Uani 1 1 d .
C8 C 0.1299(13) 0.3957(3) 0.3787(12) 0.044(2) Uani 1 1 d .
H8 H 0.2307 0.3878 0.3522 0.053 Uiso 1 1 calc R
C12 C -0.0377(12) 0.3852(3) 0.5631(12) 0.047(2) Uani 1 1 d .
H12 H -0.0473 0.3714 0.6615 0.056 Uiso 1 1 calc R
C9 C 0.0012(14) 0.4292(3) 0.2775(12) 0.050(2) Uani 1 1 d .
C10 C -0.1549(13) 0.4399(3) 0.3111(13) 0.052(2) Uani 1 1 d .
C11 C -0.1699(13) 0.4178(3) 0.4562(15) 0.057(3) Uani 1 1 d .
C18 C -0.3215(17) 0.4195(4) 0.6530(18) 0.089(4) Uani 1 1 d .
H18A H -0.3387 0.3860 0.6596 0.134 Uiso 1 1 calc R
H18B H -0.4198 0.4361 0.6696 0.134 Uiso 1 1 calc R
H18C H -0.2024 0.4286 0.7447 0.134 Uiso 1 1 calc R
C14 C 0.1781(18) 0.4469(4) 0.1096(18) 0.094(4) Uani 1 1 d .
H14A H 0.2867 0.4504 0.2205 0.141 Uiso 1 1 calc R
H14B H 0.1818 0.4701 0.0258 0.141 Uiso 1 1 calc R
H14C H 0.1769 0.4157 0.0627 0.141 Uiso 1 1 calc R
O17 O -0.3266(10) 0.4310(3) 0.4831(11) 0.074(2) Uani 1 1 d .
O13 O 0.0127(11) 0.4536(2) 0.1392(10) 0.072(2) Uani 1 1 d .
O15 O -0.2928(11) 0.4688(2) 0.1981(10) 0.076(2) Uani 1 1 d .
C16 C -0.2961(18) 0.5136(3) 0.2595(17) 0.085(4) Uani 1 1 d .
H16A H -0.3318 0.5122 0.3577 0.127 Uiso 1 1 calc R
H16B H -0.3851 0.5324 0.1653 0.127 Uiso 1 1 calc R
H16C H -0.1738 0.5275 0.2988 0.127 Uiso 1 1 calc R
C24 C 0.5586(13) 0.3058(3) 1.3523(12) 0.054(2) Uani 1 1 d .
H24A H 0.6792 0.3125 1.4466 0.082 Uiso 1 1 calc R
H24B H 0.4819 0.2898 1.4005 0.082 Uiso 1 1 calc R
H24C H 0.4994 0.3349 1.2974 0.082 Uiso 1 1 calc R
Cl2 Cl 0.1414(3) 0.19082(8) 0.9739(3) 0.0501(6) Uani 1 1 d .
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'
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'
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'
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
C21 Ir1 C21 36.8(5) . 4_565
C21 Ir1 Cl2 92.1(2) 4_565 .
C21 Ir1 Cl2 118.1(2) . .
C21 Ir1 Cl2 92.1(2) . 4_565
C21 Ir1 Cl2 118.1(2) 4_565 4_565
C20 Ir1 C21 63.9(3) . 4_565
C20 Ir1 C21 39.0(3) . .
C20 Ir1 C21 63.9(3) 4_565 .
C20 Ir1 C21 39.0(3) 4_565 4_565
C20 Ir1 C20 64.6(5) 4_565 .
C20 Ir1 Cl2 100.1(2) . 4_565
C20 Ir1 Cl2 155.6(2) 4_565 4_565
C20 Ir1 Cl2 100.1(2) 4_565 .
C20 Ir1 Cl2 155.6(2) . .
C19 Ir1 C21 64.3(4) . 4_565
C19 Ir1 C21 64.3(4) . .
C19 Ir1 C20 38.5(3) . .
C19 Ir1 C20 38.5(3) . 4_565
C19 Ir1 Cl2 136.27(6) . 4_565
C19 Ir1 Cl2 136.28(6) . .
C3 Ir1 C21 151.0(3) . .
C3 Ir1 C21 151.0(3) . 4_565
C3 Ir1 C20 112.2(3) . .
C3 Ir1 C20 112.2(3) . 4_565
C3 Ir1 C19 94.4(4) . .
C3 Ir1 Cl2 90.8(2) . 4_565
C3 Ir1 Cl2 90.8(2) . .
Cl2 Ir1 Cl2 86.88(10) . 4_565
C3 N4 C5 111.5(7) . .
C3 N4 C6 124.5(7) . .
C5 N4 C6 122.5(6) . .
C21 C21 Ir1 71.6(2) 4_565 .
C21 C21 C20 108.2(5) 4_565 .
C21 C21 C24 125.7(5) 4_565 .
C20 C21 Ir1 68.5(5) . .
C20 C21 C24 126.1(8) . .
C24 C21 Ir1 126.8(6) . .
C21 C20 Ir1 72.5(4) . .
C21 C20 C23 124.0(8) . .
C19 C20 Ir1 69.8(6) . .
C19 C20 C21 107.2(8) . .
C19 C20 C23 128.2(8) . .
C23 C20 Ir1 130.3(6) . .
C20 C19 Ir1 71.7(5) . .
C20 C19 Ir1 71.7(5) 4_565 .
C20 C19 C20 109.3(11) 4_565 .
C20 C19 C22 125.3(5) 4_565 .
C20 C19 C22 125.3(5) . .
C22 C19 Ir1 125.4(9) . .
N4 C3 Ir1 127.9(5) 4_565 .
N4 C3 Ir1 127.9(5) . .
N4 C3 N4 103.8(9) . 4_565
C5 C5 N4 106.6(4) 4_565 .
N4 C6 C7 112.9(7) . .
C8 C7 C6 121.1(7) . .
C8 C7 C12 121.9(8) . .
C12 C7 C6 117.0(8) . .
C7 C8 C9 119.9(8) . .
C7 C12 C11 117.5(8) . .
C8 C9 C10 120.7(8) . .
O13 C9 C8 124.3(8) . .
O13 C9 C10 115.0(8) . .
C9 C10 C11 117.8(8) . .
O15 C10 C9 120.4(9) . .
O15 C10 C11 121.7(8) . .
C12 C11 C10 122.1(8) . .
O17 C11 C12 123.5(9) . .
O17 C11 C10 114.4(9) . .
C11 O17 C18 115.6(8) . .
C9 O13 C14 117.1(8) . .
C10 O15 C16 115.6(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C21 2.203(9) .
Ir1 C21 2.203(9) 4_565
Ir1 C20 2.150(7) .
Ir1 C20 2.150(7) 4_565
Ir1 C19 2.125(11) .
Ir1 C3 2.061(11) .
Ir1 Cl2 2.428(2) 4_565
Ir1 Cl2 2.428(2) .
N4 C3 1.356(9) .
N4 C5 1.384(10) .
N4 C6 1.484(9) .
C21 C21 1.390(17) 4_565
C21 C20 1.453(11) .
C21 C24 1.505(11) .
C20 C19 1.408(11) .
C20 C23 1.496(12) .
C19 C20 1.408(11) 4_565
C19 C22 1.513(16) .
C3 N4 1.356(9) 4_565
C5 C5 1.343(16) 4_565
C6 C7 1.524(11) .
C7 C8 1.364(11) .
C7 C12 1.387(11) .
C8 C9 1.381(12) .
C12 C11 1.391(13) .
C9 C10 1.396(13) .
C9 O13 1.366(10) .
C10 C11 1.396(13) .
C10 O15 1.364(11) .
C11 O17 1.388(11) .
C18 O17 1.420(13) .
C14 O13 1.429(11) .
O15 C16 1.365(11) .
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
Ir1 C21 C20 C19 -61.6(7) . .
Ir1 C21 C20 C23 127.2(9) . .
Ir1 C20 C19 C20 -62.3(8) . 4_565
Ir1 C20 C19 C22 120.9(12) . .
N4 C6 C7 C8 -96.2(9) . .
N4 C6 C7 C12 85.0(9) . .
C21 Ir1 C21 C20 118.9(4) 4_565 .
C21 Ir1 C21 C24 -121.3(7) 4_565 .
C21 Ir1 C20 C21 -35.7(5) 4_565 .
C21 Ir1 C20 C19 80.8(6) 4_565 .
C21 Ir1 C20 C19 116.5(8) . .
C21 Ir1 C20 C23 -155.7(9) 4_565 .
C21 Ir1 C20 C23 -120.0(10) . .
C21 Ir1 C19 C20 38.7(5) 4_565 4_565
C21 Ir1 C19 C20 79.7(6) . 4_565
C21 Ir1 C19 C20 -38.7(5) . .
C21 Ir1 C19 C20 -79.7(6) 4_565 .
C21 Ir1 C19 C22 -159.5(3) . .
C21 Ir1 C19 C22 159.5(3) 4_565 .
C21 Ir1 C3 N4 -45.5(13) . .
C21 Ir1 C3 N4 126.7(7) . 4_565
C21 Ir1 C3 N4 -126.7(7) 4_565 .
C21 Ir1 C3 N4 45.5(13) 4_565 4_565
C21 C21 C20 Ir1 60.9(2) 4_565 .
C21 C21 C20 C19 -0.6(8) 4_565 .
C21 C21 C20 C23 -171.9(7) 4_565 .
C21 C20 C19 Ir1 63.3(6) . .
C21 C20 C19 C20 1.0(13) . 4_565
C21 C20 C19 C22 -175.8(10) . .
C20 Ir1 C21 C21 -37.8(3) 4_565 4_565
C20 Ir1 C21 C21 -118.9(4) . 4_565
C20 Ir1 C21 C20 81.1(6) 4_565 .
C20 Ir1 C21 C24 -159.1(8) 4_565 .
C20 Ir1 C21 C24 119.7(10) . .
C20 Ir1 C20 C21 -79.2(5) 4_565 .
C20 Ir1 C20 C19 37.3(6) 4_565 .
C20 Ir1 C20 C23 160.8(7) 4_565 .
C20 Ir1 C19 C20 118.4(11) . 4_565
C20 Ir1 C19 C20 -118.4(11) 4_565 .
C20 Ir1 C19 C22 120.8(5) 4_565 .
C20 Ir1 C19 C22 -120.8(5) . .
C20 Ir1 C3 N4 121.3(9) . 4_565
C20 Ir1 C3 N4 50.8(10) 4_565 4_565
C20 Ir1 C3 N4 -121.3(9) 4_565 .
C20 Ir1 C3 N4 -50.8(10) . .
C19 Ir1 C21 C21 -80.78(19) . 4_565
C19 Ir1 C21 C20 38.2(4) . .
C19 Ir1 C21 C24 157.9(8) . .
C19 Ir1 C20 C21 -116.5(8) . .
C19 Ir1 C20 C23 123.5(10) . .
C19 Ir1 C3 N4 86.1(9) . 4_565
C19 Ir1 C3 N4 -86.1(9) . .
C23 C20 C19 Ir1 -125.9(9) . .
C23 C20 C19 C20 171.8(6) . 4_565
C23 C20 C19 C22 -5.0(18) . .
C3 Ir1 C21 C21 -126.9(6) . 4_565
C3 Ir1 C21 C20 -7.9(8) . .
C3 Ir1 C21 C24 111.8(8) . .
C3 Ir1 C20 C21 175.9(4) . .
C3 Ir1 C20 C19 -67.7(6) . .
C3 Ir1 C20 C23 55.8(8) . .
C3 Ir1 C19 C20 -120.8(5) . 4_565
C3 Ir1 C19 C20 120.8(5) . .
C3 Ir1 C19 C22 0.000(6) . .
C3 N4 C5 C5 -0.4(7) . 4_565
C3 N4 C6 C7 -148.7(8) . .
C5 N4 C3 Ir1 174.2(7) . .
C5 N4 C3 N4 0.6(12) . 4_565
C5 N4 C6 C7 46.6(10) . .
C6 N4 C3 Ir1 8.1(13) . .
C6 N4 C3 N4 -165.6(5) . 4_565
C6 N4 C5 C5 166.1(6) . 4_565
C6 C7 C8 C9 -179.7(8) . .
C6 C7 C12 C11 -178.1(8) . .
C7 C8 C9 C10 -2.6(14) . .
C7 C8 C9 O13 178.1(8) . .
C7 C12 C11 C10 -1.9(14) . .
C7 C12 C11 O17 177.9(8) . .
C8 C7 C12 C11 3.1(13) . .
C8 C9 C10 C11 3.7(14) . .
C8 C9 C10 O15 -172.3(8) . .
C8 C9 O13 C14 -6.0(14) . .
C12 C7 C8 C9 -0.9(13) . .
C12 C11 O17 C18 16.3(14) . .
C9 C10 C11 C12 -1.4(14) . .
C9 C10 C11 O17 178.7(8) . .
C9 C10 O15 C16 -105.6(11) . .
C10 C9 O13 C14 174.7(10) . .
C10 C11 O17 C18 -163.8(9) . .
C11 C10 O15 C16 78.6(12) . .
O13 C9 C10 C11 -177.0(8) . .
O13 C9 C10 O15 7.1(13) . .
O15 C10 C11 C12 174.5(9) . .
O15 C10 C11 O17 -5.4(14) . .
C24 C21 C20 Ir1 -120.7(9) . .
C24 C21 C20 C19 177.7(9) . .
C24 C21 C20 C23 6.5(13) . .
Cl2 Ir1 C21 C21 49.92(11) . 4_565
Cl2 Ir1 C21 C21 137.52(10) 4_565 4_565
Cl2 Ir1 C21 C20 168.9(4) . .
Cl2 Ir1 C21 C20 -103.5(5) 4_565 .
Cl2 Ir1 C21 C24 -71.4(8) . .
Cl2 Ir1 C21 C24 16.2(7) 4_565 .
Cl2 Ir1 C20 C21 -24.4(8) . .
Cl2 Ir1 C20 C21 80.7(5) 4_565 .
Cl2 Ir1 C20 C19 92.1(7) . .
Cl2 Ir1 C20 C19 -162.8(5) 4_565 .
Cl2 Ir1 C20 C23 -39.3(8) 4_565 .
Cl2 Ir1 C20 C23 -144.4(6) . .
Cl2 Ir1 C19 C20 24.9(8) 4_565 .
Cl2 Ir1 C19 C20 -143.3(4) . .
Cl2 Ir1 C19 C20 -24.9(8) . 4_565
Cl2 Ir1 C19 C20 143.3(4) 4_565 4_565
Cl2 Ir1 C19 C22 95.9(4) . .
Cl2 Ir1 C19 C22 -95.9(4) 4_565 .
Cl2 Ir1 C3 N4 -137.4(9) 4_565 4_565
Cl2 Ir1 C3 N4 -50.5(9) . 4_565
Cl2 Ir1 C3 N4 137.4(9) . .
Cl2 Ir1 C3 N4 50.5(9) 4_565 .
