#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113178.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_4113178
loop_
_publ_author_name
'Gereon Altenhoff'
'Richard Goddard'
'Christian W. Lehmann'
'Frank Glorius'
_publ_section_title
;
 Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands
 with Restricted Flexibility for Catalysis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15195
_journal_page_last               15201
_journal_paper_doi               10.1021/ja045349r
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        d6-benzene
_chemical_formula_moiety         'C19 H24 Cl Ir N2 O4'
_chemical_formula_sum            'C19 H24 Cl Ir N2 O4'
_chemical_formula_weight         572.05
_chemical_name_common            (IBiox6)Ir(CO)2Cl
_chemical_name_systematic
; 
 Dispiro(cyclohexane-1,3'-(1,3)oxazolo(3',2':3,4)imidazolo(5,1-b)(1,3)
 oxazole-7',1"-cyclohexane-5'-ylidine))-dicarbonyl-chloro-iridium 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.399(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1029(2)
_cell_length_b                   9.5315(1)
_cell_length_c                   16.4726(2)
_cell_measurement_reflns_used    61838
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      2.04
_cell_volume                     1983.41(4)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD ω-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32725
_diffrn_reflns_theta_full        30.97
_diffrn_reflns_theta_max         30.97
_diffrn_reflns_theta_min         6.81
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.893
_exptl_absorpt_correction_T_max  0.71995
_exptl_absorpt_correction_T_min  0.33462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack, Otwinowski (1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.277
_refine_diff_density_min         -1.165
_refine_diff_density_rms         0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         6221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0226
_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)+(0.0333P)²+0.4537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0685
_reflns_number_gt                5445
_reflns_number_total             6221
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja045349rsi20040802_024138.cif
_cod_data_source_block           (IBiox6)Ir(CO)2Cl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4113178
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.2202(2) 0.4213(3) -0.03065(17) 0.0160(5) Uani 1 1 d .
C2 C 0.1110(2) 0.2582(3) -0.15296(19) 0.0193(5) Uani 1 1 d .
C3 C 0.0543(3) 0.3299(3) -0.2379(2) 0.0250(6) Uani 1 1 d .
H3A H 0.0462 0.2640 -0.2841 0.030 Uiso 1 1 calc R
H3B H -0.0153 0.3627 -0.2365 0.030 Uiso 1 1 calc R
C4 C 0.1717(2) 0.4848(3) -0.16899(19) 0.0205(6) Uani 1 1 d .
C5 C 0.2301(2) 0.5908(3) -0.12614(19) 0.0206(6) Uani 1 1 d .
C6 C 0.3316(3) 0.7666(4) -0.0590(2) 0.0270(7) Uani 1 1 d .
H6A H 0.3141 0.8621 -0.0473 0.032 Uiso 1 1 calc R
H6B H 0.4051 0.7644 -0.0606 0.032 Uiso 1 1 calc R
C7 C 0.3149(2) 0.6656(3) 0.01150(19) 0.0180(5) Uani 1 1 d .
C8 C 0.1927(2) 0.1495(3) -0.1643(2) 0.0209(6) Uani 1 1 d .
H8A H 0.2351 0.1895 -0.1986 0.025 Uiso 1 1 calc R
H8B H 0.2396 0.1265 -0.1097 0.025 Uiso 1 1 calc R
C9 C 0.1393(3) 0.0158(3) -0.2060(2) 0.0264(6) Uani 1 1 d .
H9A H 0.0986 0.0365 -0.2631 0.032 Uiso 1 1 calc R
H9B H 0.1928 -0.0530 -0.2087 0.032 Uiso 1 1 calc R
C10 C 0.0666(3) -0.0439(3) -0.1565(2) 0.0294(7) Uani 1 1 d .
H10A H 0.0322 -0.1275 -0.1845 0.035 Uiso 1 1 calc R
H10B H 0.1082 -0.0705 -0.1007 0.035 Uiso 1 1 calc R
C11 C -0.0169(2) 0.0623(3) -0.1490(2) 0.0283(7) Uani 1 1 d .
H11A H -0.0610 0.0226 -0.1159 0.034 Uiso 1 1 calc R
H11B H -0.0619 0.0839 -0.2045 0.034 Uiso 1 1 calc R
C12 C 0.0350(2) 0.1971(3) -0.1070(2) 0.0219(6) Uani 1 1 d .
H12A H -0.0195 0.2656 -0.1063 0.026 Uiso 1 1 calc R
H12B H 0.0731 0.1771 -0.0492 0.026 Uiso 1 1 calc R
C13 C 0.4199(2) 0.6214(3) 0.0707(2) 0.0221(6) Uani 1 1 d .
H13A H 0.4661 0.5858 0.0382 0.027 Uiso 1 1 calc R
H13B H 0.4081 0.5466 0.1071 0.027 Uiso 1 1 calc R
C14 C 0.4738(2) 0.7462(3) 0.1249(2) 0.0249(6) Uani 1 1 d .
H14A H 0.5398 0.7154 0.1632 0.030 Uiso 1 1 calc R
H14B H 0.4900 0.8185 0.0888 0.030 Uiso 1 1 calc R
C15 C 0.4019(3) 0.8056(3) 0.1749(2) 0.0289(7) Uani 1 1 d .
H15A H 0.4357 0.8864 0.2067 0.035 Uiso 1 1 calc R
H15B H 0.3913 0.7356 0.2146 0.035 Uiso 1 1 calc R
C16 C 0.2950(3) 0.8492(3) 0.1181(2) 0.0286(7) Uani 1 1 d .
H16A H 0.3046 0.9280 0.0836 0.034 Uiso 1 1 calc R
H16B H 0.2494 0.8794 0.1525 0.034 Uiso 1 1 calc R
C17 C 0.2415(2) 0.7278(3) 0.0608(2) 0.0222(6) Uani 1 1 d .
H17A H 0.2218 0.6550 0.0949 0.027 Uiso 1 1 calc R
H17B H 0.1774 0.7618 0.0215 0.027 Uiso 1 1 calc R
C18 C 0.1130(3) 0.3900(3) 0.09610(19) 0.0248(6) Uani 1 1 d .
C19 C 0.2612(2) 0.2001(3) 0.1792(2) 0.0188(6) Uani 1 1 d .
Cl Cl 0.38879(6) 0.20714(8) 0.05166(5) 0.02853(17) Uani 1 1 d .
Ir Ir 0.238140(8) 0.308440(10) 0.079771(6) 0.01563(4) Uani 1 1 d .
N1 N 0.16661(18) 0.3847(2) -0.10968(15) 0.0175(5) Uani 1 1 d .
N2 N 0.25989(18) 0.5502(2) -0.04226(15) 0.0184(5) Uani 1 1 d .
O1 O 0.12038(17) 0.4475(2) -0.24864(14) 0.0245(4) Uani 1 1 d .
O2 O 0.2641(2) 0.7214(2) -0.13903(15) 0.0264(5) Uani 1 1 d .
O3 O 0.0421(2) 0.4323(3) 0.10455(19) 0.0429(6) Uani 1 1 d .
O4 O 0.27649(18) 0.1339(2) 0.23871(14) 0.0275(5) 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_publ_flag
N1 C1 N2 102.6(2) y
N1 C1 Ir 128.3(2) y
N2 C1 Ir 129.1(2) y
N1 C2 C12 112.0(2) y
N1 C2 C8 109.6(2) y
C12 C2 C8 111.8(2) y
N1 C2 C3 97.6(2) y
C12 C2 C3 113.4(2) y
C8 C2 C3 111.6(3) y
O1 C3 C2 106.8(2) y
C5 C4 O1 140.5(3) y
C5 C4 N1 106.0(3) y
O1 C4 N1 113.5(2) y
C4 C5 O2 140.3(3) y
C4 C5 N2 106.4(2) y
O2 C5 N2 113.2(3) y
O2 C6 C7 108.7(2) y
N2 C7 C13 113.1(2) y
N2 C7 C17 109.4(2) y
C13 C7 C17 110.8(3) y
N2 C7 C6 98.9(2) y
C13 C7 C6 111.4(2) y
C17 C7 C6 112.7(3) y
C9 C8 C2 111.5(2) y
C10 C9 C8 110.4(3) y
C11 C10 C9 111.2(3) y
C10 C11 C12 110.7(2) y
C2 C12 C11 111.7(3) y
C7 C13 C14 110.8(2) y
C15 C14 C13 110.3(2) y
C14 C15 C16 111.8(3) y
C15 C16 C17 111.5(3) y
C7 C17 C16 111.6(2) y
O3 C18 Ir 178.1(3) y
O4 C19 Ir 178.8(3) y
C19 Ir C18 92.64(13) y
C19 Ir C1 176.73(11) y
C18 Ir C1 90.62(11) y
C19 Ir Cl 89.85(9) y
C18 Ir Cl 176.90(10) y
C1 Ir Cl 86.89(7) y
C1 N1 C4 113.1(2) y
C1 N1 C2 137.2(2) y
C4 N1 C2 109.3(2) y
C1 N2 C5 111.9(2) y
C1 N2 C7 136.9(2) y
C5 N2 C7 110.7(2) y
C4 O1 C3 104.1(2) y
C5 O2 C6 106.1(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.351(4) y
C1 N2 1.367(3) y
C1 Ir 2.072(3) y
C2 N1 1.489(4) y
C2 C12 1.518(4) y
C2 C8 1.536(4) y
C2 C3 1.557(4) y
C3 O1 1.456(4) y
C4 C5 1.348(4) y
C4 O1 1.353(4) y
C4 N1 1.380(4) y
C5 O2 1.358(3) y
C5 N2 1.387(4) y
C6 O2 1.444(4) y
C6 C7 1.569(4) y
C7 N2 1.475(4) y
C7 C13 1.521(4) y
C7 C17 1.532(4) y
C8 C9 1.526(4) y
C9 C10 1.519(5) y
C10 C11 1.520(5) y
C11 C12 1.529(4) y
C13 C14 1.541(4) y
C14 C15 1.517(5) y
C15 C16 1.521(5) y
C16 C17 1.540(4) y
C18 O3 1.055(4) y
C18 Ir 1.897(4) y
C19 O4 1.137(4) y
C19 Ir 1.892(3) y
Cl Ir 2.3513(8) y
