#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:18:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178698 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/09/4080930.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_4080930
loop_
_publ_author_name
'O, Wylie W. N.'
'Lough, Alan J.'
'Morris, Robert H.'
_publ_section_title
;
 Primary Amine Functionalized N-Heterocyclic Carbene Complexes of Iridium:
 Synthesis, Structure, and Catalysis
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3808
_journal_paper_doi               10.1021/om400180h
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C27 H30 Ir N P, F6 P'
_chemical_formula_sum            'C27 H30 F6 Ir N P2'
_chemical_formula_weight         736.66
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.988(3)
_cell_angle_beta                 104.585(4)
_cell_angle_gamma                108.488(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0278(6)
_cell_length_b                   11.2097(8)
_cell_length_c                   13.6893(10)
_cell_measurement_reflns_used    13000
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1302.24(17)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_sigmaI/netI    0.1109
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13000
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    5.311
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.581
_refine_diff_density_min         -2.161
_refine_diff_density_rms         0.203
_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     334
_refine_ls_number_reflns         5629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0561
_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)+(0.0444P)²+2.2872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                3807
_reflns_number_total             5629
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om400180h_si_002.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1302.24(15)
_cod_database_code               4080930
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
Ir1 Ir 0.83811(4) 0.71624(4) 0.30929(3) 0.03621(14) Uani 1 1 d .
P1 P 0.5829(3) 0.6614(2) 0.26703(19) 0.0341(5) Uani 1 1 d .
N1 N 0.8420(8) 0.6430(8) 0.4369(6) 0.0391(18) Uani 1 1 d .
H1C H 0.8934 0.5880 0.4306 0.047 Uiso 1 1 calc R
H1D H 0.9001 0.7172 0.5019 0.047 Uiso 1 1 calc R
C1 C 0.7008(9) 0.5665(9) 0.4487(8) 0.036(2) Uani 1 1 d .
H1A H 0.7257 0.5350 0.5089 0.044 Uiso 1 1 calc R
H1B H 0.6353 0.4851 0.3803 0.044 Uiso 1 1 calc R
C2 C 0.6156(9) 0.6545(9) 0.4728(7) 0.0318(19) Uani 1 1 d .
C3 C 0.6000(10) 0.6895(10) 0.5744(8) 0.043(2) Uani 1 1 d .
H3A H 0.6458 0.6606 0.6276 0.052 Uiso 1 1 calc R
C4 C 0.5186(10) 0.7659(9) 0.5984(7) 0.041(2) Uani 1 1 d .
H4A H 0.5075 0.7884 0.6672 0.049 Uiso 1 1 calc R
C5 C 0.4537(10) 0.8088(10) 0.5206(8) 0.043(2) Uani 1 1 d .
H5A H 0.3971 0.8602 0.5364 0.052 Uiso 1 1 calc R
C6 C 0.4696(9) 0.7786(9) 0.4210(7) 0.039(2) Uani 1 1 d .
H6A H 0.4247 0.8097 0.3692 0.046 Uiso 1 1 calc R
C7 C 0.5522(10) 0.7016(9) 0.3953(7) 0.037(2) Uani 1 1 d .
C8 C 0.4567(9) 0.4793(9) 0.1899(7) 0.033(2) Uani 1 1 d .
C9 C 0.3125(9) 0.4253(9) 0.1915(7) 0.034(2) Uani 1 1 d .
H9A H 0.2775 0.4825 0.2332 0.041 Uiso 1 1 calc R
C10 C 0.2195(10) 0.2881(9) 0.1321(7) 0.038(2) Uani 1 1 d .
H10A H 0.1203 0.2518 0.1326 0.045 Uiso 1 1 calc R
C11 C 0.2701(10) 0.2036(10) 0.0722(8) 0.042(2) Uani 1 1 d .
H11A H 0.2053 0.1100 0.0301 0.051 Uiso 1 1 calc R
C12 C 0.4148(10) 0.2564(9) 0.0741(7) 0.035(2) Uani 1 1 d .
H12A H 0.4506 0.1974 0.0351 0.042 Uiso 1 1 calc R
C13 C 0.5097(10) 0.3932(10) 0.1312(7) 0.040(2) Uani 1 1 d .
H13A H 0.6090 0.4284 0.1309 0.048 Uiso 1 1 calc R
C14 C 0.4927(10) 0.7465(9) 0.1937(7) 0.035(2) Uani 1 1 d .
C15 C 0.3655(9) 0.6757(9) 0.0977(7) 0.034(2) Uani 1 1 d .
H15A H 0.3197 0.5788 0.0681 0.041 Uiso 1 1 calc R
C16 C 0.3044(11) 0.7478(10) 0.0442(8) 0.044(2) Uani 1 1 d .
H16A H 0.2166 0.6994 -0.0211 0.052 Uiso 1 1 calc R
C17 C 0.3725(11) 0.8906(11) 0.0869(8) 0.044(2) Uani 1 1 d .
H17A H 0.3308 0.9393 0.0510 0.053 Uiso 1 1 calc R
C18 C 0.4979(11) 0.9586(10) 0.1795(8) 0.046(2) Uani 1 1 d .
H18A H 0.5450 1.0555 0.2075 0.055 Uiso 1 1 calc R
C19 C 0.5602(11) 0.8891(10) 0.2354(8) 0.041(2) Uani 1 1 d .
H19A H 0.6474 0.9387 0.3010 0.049 Uiso 1 1 calc R
C20 C 0.8716(10) 0.8398(10) 0.2135(8) 0.040(2) Uani 1 1 d .
H20A H 0.7888 0.8705 0.1934 0.048 Uiso 1 1 calc R
C21 C 0.8321(10) 0.7035(10) 0.1503(7) 0.037(2) Uani 1 1 d .
H21A H 0.7281 0.6558 0.0922 0.044 Uiso 1 1 calc R
C22 C 0.9447(10) 0.6471(10) 0.1237(7) 0.044(2) Uani 1 1 d .
H22A H 0.9689 0.6713 0.0640 0.053 Uiso 1 1 calc R
H22B H 0.8963 0.5464 0.0969 0.053 Uiso 1 1 calc R
C23 C 1.0944(10) 0.7018(9) 0.2234(7) 0.040(2) Uani 1 1 d .
H23A H 1.1400 0.6351 0.2133 0.048 Uiso 1 1 calc R
H23B H 1.1668 0.7883 0.2267 0.048 Uiso 1 1 calc R
C24 C 1.0686(9) 0.7268(10) 0.3309(7) 0.036(2) Uani 1 1 d .
H24A H 1.0965 0.6699 0.3701 0.043 Uiso 1 1 calc R
C25 C 1.0782(10) 0.8489(10) 0.3998(8) 0.045(2) Uani 1 1 d .
H25A H 1.1136 0.8637 0.4791 0.054 Uiso 1 1 calc R
C26 C 1.1142(10) 0.9787(9) 0.3796(8) 0.048(3) Uani 1 1 d .
H26A H 1.2244 1.0230 0.3969 0.058 Uiso 1 1 calc R
H26B H 1.0876 1.0418 0.4293 0.058 Uiso 1 1 calc R
C27 C 1.0285(10) 0.9535(10) 0.2613(8) 0.048(2) Uani 1 1 d .
H27A H 1.0206 1.0384 0.2585 0.058 Uiso 1 1 calc R
H27B H 1.0867 0.9303 0.2162 0.058 Uiso 1 1 calc R
F1 F 0.9517(7) 0.3858(6) 0.2157(5) 0.0613(16) Uani 1 1 d .
F2 F 0.9676(6) 0.4276(6) 0.3907(4) 0.0546(15) Uani 1 1 d .
F3 F 1.0608(6) 0.2847(6) 0.3130(4) 0.0534(14) Uani 1 1 d .
F4 F 0.8347(6) 0.1590(6) 0.1726(4) 0.0585(15) Uani 1 1 d .
F5 F 0.8505(6) 0.1992(6) 0.3474(4) 0.0562(15) Uani 1 1 d .
F6 F 0.7394(6) 0.3009(7) 0.2500(5) 0.0652(17) Uani 1 1 d .
P2 P 0.8990(3) 0.2925(3) 0.2806(2) 0.0415(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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Ir Ir -1.4442 7.9887 '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
N1 Ir1 C21 154.6(3)
N1 Ir1 C20 165.4(3)
C21 Ir1 C20 38.1(3)
N1 Ir1 C25 88.3(3)
C21 Ir1 C25 97.9(3)
C20 Ir1 C25 80.5(4)
N1 Ir1 C24 88.8(3)
C21 Ir1 C24 81.9(3)
C20 Ir1 C24 87.7(3)
C25 Ir1 C24 36.9(3)
N1 Ir1 P1 89.64(19)
C21 Ir1 P1 95.0(2)
C20 Ir1 P1 96.4(2)
C25 Ir1 P1 154.0(3)
C24 Ir1 P1 169.0(3)
C7 P1 C14 104.7(4)
C7 P1 C8 103.9(4)
C14 P1 C8 103.6(4)
C7 P1 Ir1 107.4(3)
C14 P1 Ir1 120.0(3)
C8 P1 Ir1 115.6(3)
C1 N1 Ir1 121.5(5)
N1 C1 C2 111.3(7)
C3 C2 C7 119.4(8)
C3 C2 C1 119.1(7)
C7 C2 C1 121.5(7)
C4 C3 C2 121.0(8)
C5 C4 C3 119.0(8)
C6 C5 C4 121.4(8)
C5 C6 C7 120.4(8)
C6 C7 C2 118.7(8)
C6 C7 P1 123.1(7)
C2 C7 P1 118.2(6)
C9 C8 C13 119.7(8)
C9 C8 P1 121.2(6)
C13 C8 P1 119.0(6)
C10 C9 C8 120.0(8)
C11 C10 C9 120.4(8)
C12 C11 C10 119.4(9)
C11 C12 C13 121.6(8)
C12 C13 C8 118.8(8)
C15 C14 C19 119.5(8)
C15 C14 P1 122.9(7)
C19 C14 P1 117.6(7)
C14 C15 C16 119.8(8)
C17 C16 C15 120.3(9)
C18 C17 C16 119.5(8)
C17 C18 C19 121.4(9)
C14 C19 C18 119.5(9)
C21 C20 C27 125.5(8)
C21 C20 Ir1 69.6(5)
C27 C20 Ir1 113.1(6)
C20 C21 C22 124.4(8)
C20 C21 Ir1 72.4(5)
C22 C21 Ir1 109.3(5)
C21 C22 C23 113.3(7)
C24 C23 C22 112.0(7)
C25 C24 C23 126.1(8)
C25 C24 Ir1 70.2(5)
C23 C24 Ir1 111.4(5)
C24 C25 C26 125.4(9)
C24 C25 Ir1 72.9(5)
C26 C25 Ir1 109.2(6)
C25 C26 C27 112.3(8)
C20 C27 C26 112.4(7)
F6 P2 F4 90.6(3)
F6 P2 F1 90.4(3)
F4 P2 F1 90.4(3)
F6 P2 F3 179.4(4)
F4 P2 F3 89.9(3)
F1 P2 F3 89.9(3)
F6 P2 F5 91.1(3)
F4 P2 F5 90.0(3)
F1 P2 F5 178.5(3)
F3 P2 F5 88.6(3)
F6 P2 F2 90.6(3)
F4 P2 F2 178.8(3)
F1 P2 F2 89.6(3)
F3 P2 F2 88.9(3)
F5 P2 F2 90.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ir1 N1 2.123(6)
Ir1 C21 2.126(8)
Ir1 C20 2.162(8)
Ir1 C25 2.180(9)
Ir1 C24 2.215(7)
Ir1 P1 2.307(2)
P1 C7 1.818(9)
P1 C14 1.832(8)
P1 C8 1.840(9)
N1 C1 1.479(10)
C1 C2 1.519(11)
C2 C3 1.400(11)
C2 C7 1.411(11)
C3 C4 1.390(12)
C4 C5 1.386(12)
C5 C6 1.374(12)
C6 C7 1.410(11)
C8 C9 1.388(11)
C8 C13 1.404(11)
C9 C10 1.384(12)
C10 C11 1.384(12)
C11 C12 1.373(12)
C12 C13 1.381(13)
C14 C15 1.387(12)
C14 C19 1.399(12)
C15 C16 1.405(11)
C16 C17 1.401(13)
C17 C18 1.352(13)
C18 C19 1.407(12)
C20 C21 1.399(12)
C20 C27 1.510(13)
C21 C22 1.529(11)
C22 C23 1.554(12)
C23 C24 1.524(11)
C24 C25 1.391(13)
C25 C26 1.504(12)
C26 C27 1.528(13)
F1 P2 1.601(6)
F2 P2 1.612(6)
F3 P2 1.608(5)
F4 P2 1.591(6)
F5 P2 1.611(6)
F6 P2 1.588(6)
