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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/4/11/14/4111444.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_4111444
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            'C23 H28 F6 Ir N4 P'
_chemical_formula_weight         697.66
_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             2001-11-27
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.193(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1802(19)
_cell_length_b                   11.5828(18)
_cell_length_c                   23.581(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.478
_cell_measurement_theta_min      10.384
_cell_volume                     2459.7(8)
_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),
DIFABS (Walker & Stuart, 1983)
;
_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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5961
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        7.373
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.558
_exptl_absorpt_correction_T_max  0.513
_exptl_absorpt_correction_T_min  0.272
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            brown-red
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_description       'rounded lump'
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.249
_refine_diff_density_min         -2.322
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.064
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0529
_refine_ls_R_factor_obs          0.0529
_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)+(0.0553P)²+10.7359P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1314
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_obs         0.1150
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                3815
_reflns_number_observed          3815
_reflns_number_total             5616
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0439470si20041116_095112_2.cif
_cod_data_source_block           THEP17
_cod_original_cell_volume        2459.7(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4111444
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 0.09425(4) 0.19506(3) 0.142305(14) 0.04476(12) Uani 1 d .
C1 C 0.1924(12) 0.0601(8) 0.1909(4) 0.061(3) Uani 1 d .
H1A H 0.3001 0.0597 0.1995 0.073 Uiso 1 calc R
H1B H 0.1490 0.0385 0.2238 0.073 Uiso 1 calc R
C2 C 0.1222(12) 0.0122(8) 0.1355(4) 0.064(3) Uani 1 d .
H2A H 0.0351 -0.0356 0.1347 0.077 Uiso 1 calc R
H2B H 0.1870 -0.0143 0.1103 0.077 Uiso 1 calc R
N1 N 0.2919(8) 0.2507(7) 0.1212(3) 0.0515(18) Uani 1 d .
N2 N -0.0943(9) 0.1793(6) 0.1757(3) 0.0528(19) Uani 1 d .
N3 N -0.0252(8) 0.3288(7) 0.0805(3) 0.0497(18) Uani 1 d .
N4 N 0.1187(10) 0.3493(7) 0.1943(3) 0.058(2) Uani 1 d .
C11 C 0.2854(13) 0.3621(10) 0.2083(5) 0.073(3) Uani 1 d .
H11A H 0.3112 0.4395 0.2224 0.088 Uiso 1 calc R
H11B H 0.3270 0.3079 0.2385 0.088 Uiso 1 calc R
C12 C 0.3504(12) 0.3397(8) 0.1554(4) 0.059(2) Uani 1 d .
C13 C 0.4687(14) 0.4029(11) 0.1453(6) 0.088(4) Uani 1 d .
H13 H 0.5051 0.4647 0.1691 0.106 Uiso 1 calc R
C14 C 0.5328(14) 0.3728(12) 0.0990(6) 0.085(4) Uani 1 d .
H14 H 0.6132 0.4149 0.0916 0.102 Uiso 1 calc R
C15 C 0.4807(12) 0.2835(10) 0.0645(5) 0.070(3) Uani 1 d .
H15 H 0.5257 0.2627 0.0339 0.084 Uiso 1 calc R
C16 C 0.3569(11) 0.2223(9) 0.0756(4) 0.058(2) Uani 1 d .
C17 C 0.3038(15) 0.1241(11) 0.0388(5) 0.088(4) Uani 1 d .
H17A H 0.3638 0.0577 0.0516 0.132 Uiso 1 calc R
H17B H 0.3102 0.1416 -0.0004 0.132 Uiso 1 calc R
H17C H 0.2024 0.1083 0.0410 0.132 Uiso 1 calc R
C21 C 0.0599(13) 0.3094(9) 0.2452(4) 0.068(3) Uani 1 d .
H21A H 0.0445 0.3752 0.2688 0.082 Uiso 1 calc R
H21B H 0.1313 0.2584 0.2685 0.082 Uiso 1 calc R
C22 C -0.0854(12) 0.2462(9) 0.2258(4) 0.060(2) Uani 1 d .
C23 C -0.1972(14) 0.2511(11) 0.2563(5) 0.073(3) Uani 1 d .
H23 H -0.1879 0.2970 0.2892 0.088 Uiso 1 calc R
C24 C -0.3228(14) 0.1879(11) 0.2379(6) 0.080(3) Uani 1 d .
H24 H -0.3993 0.1889 0.2586 0.096 Uiso 1 calc R
C25 C -0.3351(12) 0.1232(10) 0.1888(5) 0.068(3) Uani 1 d .
H25 H -0.4203 0.0796 0.1762 0.082 Uiso 1 calc R
C26 C -0.2210(12) 0.1218(9) 0.1574(4) 0.062(3) Uani 1 d .
C27 C -0.2435(13) 0.0609(10) 0.1012(5) 0.073(3) Uani 1 d .
H27A H -0.3125 0.1034 0.0730 0.110 Uiso 1 calc R
H27B H -0.2824 -0.0149 0.1054 0.110 Uiso 1 calc R
H27C H -0.1504 0.0546 0.0886 0.110 Uiso 1 calc R
C31 C 0.0433(15) 0.4515(9) 0.1650(5) 0.086(4) Uani 1 d .
H31A H -0.0268 0.4799 0.1877 0.103 Uiso 1 calc R
H31B H 0.1168 0.5114 0.1646 0.103 Uiso 1 calc R
C32 C -0.0360(10) 0.4326(8) 0.1060(4) 0.054(2) Uani 1 d .
C33 C -0.1155(12) 0.5218(9) 0.0763(5) 0.071(3) Uani 1 d .
H33 H -0.1191 0.5929 0.0943 0.085 Uiso 1 calc R
C34 C -0.1884(13) 0.5075(12) 0.0210(6) 0.082(4) Uani 1 d .
H34 H -0.2455 0.5666 0.0012 0.099 Uiso 1 calc R
C35 C -0.1755(12) 0.4038(12) -0.0046(5) 0.077(3) Uani 1 d .
H35 H -0.2221 0.3928 -0.0429 0.092 Uiso 1 calc R
C36 C -0.0949(10) 0.3147(9) 0.0249(4) 0.058(2) Uani 1 d .
C37 C -0.0801(14) 0.2021(11) -0.0041(5) 0.081(3) Uani 1 d .
H37A H -0.0539 0.1430 0.0245 0.122 Uiso 1 calc R
H37B H -0.0041 0.2081 -0.0268 0.122 Uiso 1 calc R
H37C H -0.1728 0.1828 -0.0289 0.122 Uiso 1 calc R
P1 P 0.4601(4) 0.2476(3) 0.37931(13) 0.0710(8) Uani 1 d .
F1 F 0.6212(9) 0.2114(8) 0.3714(3) 0.116(3) Uani 1 d .
F2 F 0.2995(9) 0.2804(7) 0.3877(5) 0.124(3) Uani 1 d .
F3 F 0.4635(9) 0.1450(7) 0.4237(3) 0.102(2) Uani 1 d .
F4 F 0.5293(9) 0.3303(6) 0.4309(3) 0.092(2) Uani 1 d .
F5 F 0.4581(12) 0.3497(8) 0.3359(3) 0.129(3) Uani 1 d .
F6 F 0.3914(10) 0.1660(7) 0.3273(3) 0.108(3) 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
C1 Ir1 N2 91.7(4) y
C1 Ir1 N1 93.5(4) y
N2 Ir1 N1 164.9(3) y
C1 Ir1 C2 40.5(4) y
N2 Ir1 C2 93.6(3) y
N1 Ir1 C2 99.5(4) y
C1 Ir1 N4 109.2(4) y
N2 Ir1 N4 81.8(3) y
N1 Ir1 N4 83.1(3) y
C2 Ir1 N4 149.5(3) y
C1 Ir1 N3 173.3(3) y
N2 Ir1 N3 88.2(3) y
N1 Ir1 N3 88.3(3) y
C2 Ir1 N3 132.8(3) y
N4 Ir1 N3 77.4(3) y
C2 C1 Ir1 73.5(5) y
C1 C2 Ir1 66.0(5) y
C12 N1 C16 117.9(8) y
C12 N1 Ir1 110.9(6) y
C16 N1 Ir1 130.5(7) y
C26 N2 C22 116.8(8) y
C26 N2 Ir1 132.0(6) y
C22 N2 Ir1 111.1(6) y
C36 N3 C32 118.3(8) y
C36 N3 Ir1 128.4(7) y
C32 N3 Ir1 113.0(6) y
C31 N4 C21 114.7(9) y
C31 N4 C11 112.9(9) y
C21 N4 C11 111.5(8) y
C31 N4 Ir1 114.3(6) y
C21 N4 Ir1 100.8(6) y
C11 N4 Ir1 101.2(6) y
C12 C11 N4 110.5(8) y
N1 C12 C13 122.7(11) y
N1 C12 C11 116.7(9) y
C13 C12 C11 120.4(11) y
C12 C13 C14 118.4(12) y
C15 C14 C13 121.1(11) y
C14 C15 C16 118.7(11) y
N1 C16 C15 121.1(10) y
N1 C16 C17 120.6(9) y
C15 C16 C17 118.2(10) y
N4 C21 C22 110.2(8) y
C23 C22 N2 122.8(11) y
C23 C22 C21 122.0(10) y
N2 C22 C21 115.2(8) y
C22 C23 C24 119.1(11) y
C23 C24 C25 119.3(11) y
C24 C25 C26 120.6(11) y
N2 C26 C25 121.2(10) y
N2 C26 C27 119.2(9) y
C25 C26 C27 119.5(10) y
C32 C31 N4 115.4(8) y
N3 C32 C33 121.2(10) y
N3 C32 C31 119.4(8) y
C33 C32 C31 119.4(10) y
C34 C33 C32 120.8(11) y
C33 C34 C35 117.8(11) y
C34 C35 C36 121.4(11) y
N3 C36 C35 120.4(10) y
N3 C36 C37 118.9(9) y
C35 C36 C37 120.7(10) y
F5 P1 F2 90.4(6) y
F5 P1 F6 89.6(5) y
F2 P1 F6 90.0(5) y
F5 P1 F3 179.3(5) y
F2 P1 F3 89.8(5) y
F6 P1 F3 91.0(5) y
F5 P1 F4 89.8(5) y
F2 P1 F4 90.2(5) y
F6 P1 F4 179.4(5) y
F3 P1 F4 89.6(4) y
F5 P1 F1 90.9(5) y
F2 P1 F1 178.5(6) y
F6 P1 F1 89.5(5) y
F3 P1 F1 88.8(5) y
F4 P1 F1 90.4(5) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 C1 2.042(9) y
Ir1 N2 2.043(8) y
Ir1 N1 2.075(7) y
Ir1 C2 2.143(9) y
Ir1 N4 2.154(8) y
Ir1 N3 2.260(7) y
C1 C2 1.451(13) y
N1 C12 1.354(12) y
N1 C16 1.366(12) y
N2 C26 1.337(12) y
N2 C22 1.404(12) y
N3 C36 1.352(11) y
N3 C32 1.355(12) y
N4 C31 1.473(12) y
N4 C21 1.483(12) y
N4 C11 1.509(14) y
C11 C12 1.506(14) y
C12 C13 1.368(15) y
C13 C14 1.382(17) y
C14 C15 1.345(17) y
C15 C16 1.407(14) y
C16 C17 1.456(15) y
C21 C22 1.512(15) y
C22 C23 1.363(14) y
C23 C24 1.363(17) y
C24 C25 1.366(16) y
C25 C26 1.396(14) y
C26 C27 1.480(14) y
C31 C32 1.458(14) y
C32 C33 1.376(13) y
C33 C34 1.355(16) y
C34 C35 1.360(17) y
C35 C36 1.378(15) y
C36 C37 1.492(14) y
P1 F5 1.562(9) y
P1 F2 1.571(9) y
P1 F6 1.579(8) y
P1 F3 1.580(8) y
P1 F4 1.582(7) y
P1 F1 1.583(8) y
