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#$Date: 2016-03-22 11:06:59 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178885 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/14/4111446.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_4111446
loop_
_publ_author_name
'Dennis G. H. Hetterscheid'
'Jasper Kaiser'
'Eduard Reijerse'
'Theo P. J. Peters'
'Simone Thewissen'
'Arno N. J. Blok'
'Jan M. M. Smits'
'René de Gelder'
'Bas de Bruin'
_publ_contact_author
;
        Dr. B. de Bruin
        Department of Metal-Organic Chemistry
        Institute for Molecules and Materials
        Radboud University Nijmegen
        Toernooiveld 1
        NL-6525 ED  Nijmegen
        The Netherlands
;
_publ_contact_author_email       BdeBruin@sci.kun.nl
_publ_contact_author_fax         '031 024 3553450'
_publ_contact_author_phone       '031 024 3652464'
_publ_section_title
;
 IrII(ethene): Metal or Carbon Radical?
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1895
_journal_page_last               1905
_journal_paper_doi               10.1021/ja0439470
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C22 H26 F6 Ir N4 P'
_chemical_formula_weight         683.64
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2002-07-12
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 116.392(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9423(10)
_cell_length_b                   13.2295(14)
_cell_length_c                   14.7294(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.331
_cell_measurement_theta_min      10.267
_cell_volume                     2433.7(5)
_computing_data_collection
;
CAD4 EXPRESS (Enraf-Nonius, 1994)
;
_computing_data_reduction
;
local programs (Smits et al., 1988),
profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978),
EMPABS (North et al., 1968)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003),
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
DIRDIF (Beurskens et al., 1996),
PATTY (Beurskens et al., 1987)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measurement_device       'Nonius CAD4'
_diffrn_measurement_method       ω/2θ-scan
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5783
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.78
_diffrn_standards_decay_%        4.147
_diffrn_standards_interval_time  6940
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.616
_exptl_absorpt_correction_T_max  0.232
_exptl_absorpt_correction_T_min  0.067
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_description       'rather regular fragment'
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.26
_refine_diff_density_max         2.909
_refine_diff_density_min         -1.382
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.106
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0444
_refine_ls_R_factor_obs          0.0444
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_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)+(0.0646P)²+3.2862P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1140
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_obs         0.1066
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                4362
_reflns_number_observed          4362
_reflns_number_total             5560
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0439470si20041116_095112_4.cif
_cod_data_source_block           TYUEN5
_cod_original_cell_volume        2433.7(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4111446
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_calc_flag
_atom_site_refinement_flags
Ir1 Ir 0.224988(18) 0.227670(18) 0.192503(17) 0.03783(10) Uani 1 d .
N1 N 0.2815(5) 0.3392(5) 0.2990(4) 0.0533(15) Uani 1 d .
N2 N 0.1450(4) 0.1468(4) 0.0598(4) 0.0395(11) Uani 1 d .
N3 N 0.3639(4) 0.2679(4) 0.1642(4) 0.0433(12) Uani 1 d .
N4 N 0.1625(4) 0.3520(4) 0.0881(4) 0.0457(12) Uani 1 d .
C1 C 0.2272(7) 0.1185(6) 0.2944(5) 0.0557(17) Uani 1 d .
H1A H 0.2230 0.0486 0.2731 0.067 Uiso 1 calc R
H1B H 0.2761 0.1295 0.3652 0.067 Uiso 1 calc R
C2 C 0.1284(6) 0.1749(6) 0.2541(6) 0.0576(18) Uani 1 d .
H2A H 0.1174 0.2197 0.3007 0.069 Uiso 1 calc R
H2B H 0.0644 0.1388 0.2087 0.069 Uiso 1 calc R
C11 C 0.1563(6) 0.4365(6) 0.1530(7) 0.063(2) Uani 1 d .
H11A H 0.1611 0.5004 0.1230 0.076 Uiso 1 calc R
H11B H 0.0872 0.4341 0.1539 0.076 Uiso 1 calc R
C12 C 0.2422(6) 0.4323(6) 0.2592(6) 0.0588(19) Uani 1 d .
C13 C 0.2763(7) 0.5162(8) 0.3194(8) 0.079(3) Uani 1 d .
H13 H 0.2511 0.5796 0.2919 0.095 Uiso 1 calc R
C14 C 0.3471(9) 0.5077(9) 0.4196(9) 0.094(4) Uani 1 d .
H14 H 0.3694 0.5646 0.4608 0.113 Uiso 1 calc R
C15 C 0.3843(9) 0.4144(10) 0.4581(8) 0.091(3) Uani 1 d .
H15 H 0.4324 0.4069 0.5261 0.109 Uiso 1 calc R
C16 C 0.3506(7) 0.3317(7) 0.3961(6) 0.066(2) Uani 1 d .
H16 H 0.3769 0.2683 0.4229 0.080 Uiso 1 calc R
C21 C 0.0590(5) 0.3123(6) 0.0159(6) 0.0560(17) Uani 1 d .
H21A H 0.0301 0.3546 -0.0441 0.067 Uiso 1 calc R
H21B H 0.0096 0.3141 0.0459 0.067 Uiso 1 calc R
C22 C 0.0689(5) 0.2068(5) -0.0134(5) 0.0428(14) Uani 1 d .
C23 C 0.0044(6) 0.1708(7) -0.1087(5) 0.0588(19) Uani 1 d .
H23 H -0.0468 0.2127 -0.1565 0.071 Uiso 1 calc R
C24 C 0.0158(7) 0.0720(7) -0.1333(6) 0.068(2) Uani 1 d .
H24 H -0.0273 0.0462 -0.1975 0.081 Uiso 1 calc R
C25 C 0.0915(6) 0.0142(6) -0.0614(6) 0.0597(19) Uani 1 d .
H25 H 0.1004 -0.0522 -0.0768 0.072 Uiso 1 calc R
C26 C 0.1558(5) 0.0508(5) 0.0339(5) 0.0457(15) Uani 1 d .
C27 C 0.2414(6) -0.0148(6) 0.1096(6) 0.063(2) Uani 1 d .
H27A H 0.2984 0.0269 0.1562 0.095 Uiso 1 calc R
H27B H 0.2687 -0.0592 0.0750 0.095 Uiso 1 calc R
H27C H 0.2120 -0.0541 0.1460 0.095 Uiso 1 calc R
C31 C 0.2317(5) 0.3772(6) 0.0388(5) 0.0541(17) Uani 1 d .
H31A H 0.2279 0.4494 0.0260 0.065 Uiso 1 calc R
H31B H 0.2047 0.3429 -0.0261 0.065 Uiso 1 calc R
C32 C 0.3461(5) 0.3480(5) 0.1011(5) 0.0434(14) Uani 1 d .
C33 C 0.4293(6) 0.3980(6) 0.0922(6) 0.0566(18) Uani 1 d .
H33 H 0.4152 0.4540 0.0500 0.068 Uiso 1 calc R
C34 C 0.5316(7) 0.3643(8) 0.1461(8) 0.079(3) Uani 1 d .
H34 H 0.5881 0.3972 0.1412 0.094 Uiso 1 calc R
C35 C 0.5503(7) 0.2814(7) 0.2074(9) 0.075(3) Uani 1 d .
H35 H 0.6195 0.2566 0.2430 0.090 Uiso 1 calc R
C36 C 0.4663(6) 0.2345(6) 0.2164(6) 0.0557(18) Uani 1 d .
C37 C 0.4853(6) 0.1450(7) 0.2854(7) 0.078(3) Uani 1 d .
H37A H 0.5457 0.1583 0.3494 0.116 Uiso 1 calc R
H37B H 0.4995 0.0863 0.2550 0.116 Uiso 1 calc R
H37C H 0.4230 0.1334 0.2958 0.116 Uiso 1 calc R
P1 P 0.78091(15) 0.18746(16) 0.56099(17) 0.0592(5) Uani 1 d .
F1 F 0.6843(6) 0.2629(5) 0.5129(7) 0.121(3) Uani 1 d .
F2 F 0.7772(7) 0.1684(9) 0.4542(6) 0.151(4) Uani 1 d .
F3 F 0.8776(4) 0.1109(5) 0.6062(5) 0.103(2) Uani 1 d .
F4 F 0.7819(6) 0.1972(9) 0.6665(5) 0.146(3) Uani 1 d .
F5 F 0.8631(7) 0.2725(5) 0.5838(12) 0.192(6) Uani 1 d .
F6 F 0.6977(5) 0.1005(5) 0.5359(6) 0.108(2) Uani 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'
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'
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'
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 Ir1 C2 90.7(3) y
N1 Ir1 N2 164.5(2) y
C2 Ir1 N2 93.3(3) y
N1 Ir1 C1 94.1(3) y
C2 Ir1 C1 40.9(3) y
N2 Ir1 C1 98.8(3) y
N1 Ir1 N4 83.8(3) y
C2 Ir1 N4 116.0(3) y
N2 Ir1 N4 81.0(2) y
C1 Ir1 N4 156.9(3) y
N1 Ir1 N3 84.2(2) y
C2 Ir1 N3 164.5(3) y
N2 Ir1 N3 95.5(2) y
C1 Ir1 N3 124.7(3) y
N4 Ir1 N3 78.0(2) y
C16 N1 C12 119.3(7) y
C16 N1 Ir1 128.5(6) y
C12 N1 Ir1 112.1(5) y
C26 N2 C22 117.6(5) y
C26 N2 Ir1 132.2(4) y
C22 N2 Ir1 110.2(4) y
C32 N3 C36 117.8(6) y
C32 N3 Ir1 114.0(4) y
C36 N3 Ir1 126.9(5) y
C21 N4 C31 111.9(6) y
C21 N4 C11 114.5(6) y
C31 N4 C11 112.3(6) y
C21 N4 Ir1 101.6(4) y
C31 N4 Ir1 112.2(4) y
C11 N4 Ir1 103.6(4) y
C2 C1 Ir1 68.7(4) y
C1 C2 Ir1 70.4(4) y
C12 C11 N4 113.2(6) y
C13 C12 N1 119.6(8) y
C13 C12 C11 122.4(9) y
N1 C12 C11 117.7(7) y
C12 C13 C14 120.6(10) y
C15 C14 C13 118.9(9) y
C14 C15 C16 119.6(10) y
N1 C16 C15 122.0(10) y
N4 C21 C22 111.1(6) y
C23 C22 N2 121.8(7) y
C23 C22 C21 121.3(6) y
N2 C22 C21 116.9(6) y
C22 C23 C24 119.7(7) y
C25 C24 C23 118.0(7) y
C24 C25 C26 122.0(8) y
N2 C26 C25 120.9(7) y
N2 C26 C27 119.1(6) y
C25 C26 C27 119.9(7) y
N4 C31 C32 113.0(6) y
N3 C32 C33 122.0(6) y
N3 C32 C31 116.3(6) y
C33 C32 C31 121.7(6) y
C34 C33 C32 119.4(7) y
C33 C34 C35 119.2(7) y
C34 C35 C36 120.1(8) y
N3 C36 C35 121.5(7) y
N3 C36 C37 117.6(7) y
C35 C36 C37 121.0(7) y
F5 P1 F4 92.6(7) y
F5 P1 F6 178.8(7) y
F4 P1 F6 88.5(5) y
F5 P1 F1 92.3(5) y
F4 P1 F1 91.3(5) y
F6 P1 F1 87.9(4) y
F5 P1 F2 91.5(7) y
F4 P1 F2 175.4(7) y
F6 P1 F2 87.4(5) y
F1 P1 F2 90.6(5) y
F5 P1 F3 87.9(4) y
F4 P1 F3 90.3(4) y
F6 P1 F3 91.9(4) y
F1 P1 F3 178.3(5) y
F2 P1 F3 87.7(4) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 N1 2.039(6) y
Ir1 C2 2.051(7) y
Ir1 N2 2.066(5) y
Ir1 C1 2.073(7) y
Ir1 N4 2.153(5) y
Ir1 N3 2.219(6) y
N1 C16 1.326(9) y
N1 C12 1.370(11) y
N2 C26 1.354(9) y
N2 C22 1.378(8) y
N3 C32 1.357(8) y
N3 C36 1.360(9) y
N4 C21 1.458(9) y
N4 C31 1.482(8) y
N4 C11 1.497(9) y
C1 C2 1.442(11) y
C11 C12 1.490(11) y
C12 C13 1.367(12) y
C13 C14 1.368(14) y
C14 C15 1.361(17) y
C15 C16 1.367(12) y
C21 C22 1.485(10) y
C22 C23 1.373(10) y
C23 C24 1.385(12) y
C24 C25 1.352(11) y
C25 C26 1.374(9) y
C26 C27 1.495(10) y
C31 C32 1.495(9) y
C32 C33 1.391(9) y
C33 C34 1.363(12) y
C34 C35 1.371(13) y
C35 C36 1.382(11) y
C36 C37 1.506(11) y
P1 F5 1.533(7) y
P1 F4 1.553(7) y
P1 F6 1.557(6) y
P1 F1 1.570(6) y
P1 F2 1.571(7) y
P1 F3 1.578(6) y
