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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/4/11/14/4111449.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_4111449
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            'C21 H24 Cl F6 Ir N4 P'
_chemical_formula_weight         705.06
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             2002-11-06
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8074(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5432(2)
_cell_length_b                   16.3409(3)
_cell_length_c                   13.4964(3)
_cell_measurement_reflns_used    41246
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.400
_cell_measurement_theta_min      1.960
_cell_volume                     2317.05(8)
_computing_data_collection       'Nonius "Collect" program suite'
_computing_data_reduction        'Nonius "DENZO SMN" program suite'
_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      150(2)
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measurement_device       'Nonius KappaCCD on rotating anode'
_diffrn_measurement_method       'area detector φ and ω 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  0.0913
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            41246
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.013
_exptl_absorpt_correction_T_max  0.486
_exptl_absorpt_correction_T_min  0.375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'multiscan (Nonius DENZO SMN)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_description       'rough fragment'
_exptl_crystal_F_000             1364
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.832
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.023
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0285
_refine_ls_R_factor_obs          0.0285
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0192P)²+1.1943P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0582
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_obs         0.0528
_refine_ls_wR_factor_ref         0.0582
_reflns_number_gt                3981
_reflns_number_observed          3981
_reflns_number_total             5253
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0439470si20041116_095112_7.cif
_cod_data_source_block           TYUE7B
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4111449
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_calc_flag
_atom_site_refinement_flags
Ir1 Ir 0.178661(15) 0.070629(9) 0.105989(11) 0.01778(6) Uani 1 d .
C1 C 0.0014(4) 0.0259(3) 0.0468(3) 0.0204(9) Uani 1 d .
H1A H -0.033(4) -0.002(2) 0.102(3) 0.024 Uiso 1 d .
H1B H -0.046(4) 0.075(2) 0.037(3) 0.024 Uiso 1 d .
Cl1 Cl 0.15018(12) 0.16226(7) -0.03102(8) 0.0380(3) Uani 1 d .
N1 N 0.2665(3) -0.02658(19) 0.0383(2) 0.0189(8) Uani 1 d .
N2 N 0.0766(3) 0.13992(19) 0.1968(2) 0.0203(8) Uani 1 d .
N3 N 0.3519(3) 0.1231(2) 0.1969(2) 0.0211(8) Uani 1 d .
N4 N 0.1916(3) -0.00976(18) 0.2224(2) 0.0170(7) Uani 1 d .
C11 C 0.1711(4) -0.0935(2) 0.1767(3) 0.0250(10) Uani 1 d .
H11A H 0.0791 -0.1030 0.1599 0.030 Uiso 1 calc R
H11B H 0.2031 -0.1360 0.2248 0.030 Uiso 1 calc R
C12 C 0.2413(4) -0.0990(3) 0.0839(3) 0.0242(10) Uani 1 d .
C13 C 0.2687(4) -0.1733(3) 0.0428(3) 0.0300(11) Uani 1 d .
H13 H 0.2543 -0.2228 0.0770 0.036 Uiso 1 calc R
C14 C 0.3170(4) -0.1748(3) -0.0480(4) 0.0358(12) Uani 1 d .
H14 H 0.3305 -0.2255 -0.0798 0.043 Uiso 1 calc R
C15 C 0.3459(4) -0.1031(3) -0.0928(3) 0.0350(12) Uani 1 d .
H15 H 0.3802 -0.1041 -0.1556 0.042 Uiso 1 calc R
C16 C 0.3257(4) -0.0288(3) -0.0473(3) 0.0245(10) Uani 1 d .
C17 C 0.3698(5) 0.0481(3) -0.0908(4) 0.0432(13) Uani 1 d .
H17A H 0.2995 0.0731 -0.1323 0.065 Uiso 1 calc R
H17B H 0.4402 0.0363 -0.1316 0.065 Uiso 1 calc R
H17C H 0.3989 0.0859 -0.0373 0.065 Uiso 1 calc R
C21 C 0.0913(4) 0.0117(2) 0.2913(3) 0.0237(10) Uani 1 d .
H21A H 0.1249 0.0009 0.3607 0.028 Uiso 1 calc R
H21B H 0.0160 -0.0237 0.2762 0.028 Uiso 1 calc R
C22 C 0.0514(4) 0.1004(2) 0.2814(3) 0.0208(9) Uani 1 d .
C23 C -0.0181(4) 0.1369(3) 0.3512(3) 0.0288(11) Uani 1 d .
H23 H -0.0336 0.1084 0.4103 0.035 Uiso 1 calc R
C24 C -0.0649(5) 0.2150(3) 0.3352(3) 0.0388(12) Uani 1 d .
H24 H -0.1137 0.2405 0.3826 0.047 Uiso 1 calc R
C25 C -0.0400(5) 0.2553(3) 0.2495(3) 0.0356(12) Uani 1 d .
H25 H -0.0714 0.3091 0.2373 0.043 Uiso 1 calc R
C26 C 0.0313(4) 0.2171(3) 0.1809(3) 0.0280(10) Uani 1 d .
H26 H 0.0485 0.2453 0.1219 0.034 Uiso 1 calc R
C31 C 0.3229(4) -0.0089(2) 0.2744(3) 0.0202(9) Uani 1 d .
H31A H 0.3191 -0.0291 0.3432 0.024 Uiso 1 calc R
H31B H 0.3779 -0.0466 0.2397 0.024 Uiso 1 calc R
C32 C 0.3810(4) 0.0746(2) 0.2774(3) 0.0196(9) Uani 1 d .
C33 C 0.4663(4) 0.0966(3) 0.3558(3) 0.0274(11) Uani 1 d .
H33 H 0.4817 0.0616 0.4118 0.033 Uiso 1 calc R
C34 C 0.5289(4) 0.1705(3) 0.3513(3) 0.0323(11) Uani 1 d .
H34 H 0.5909 0.1863 0.4029 0.039 Uiso 1 calc R
C35 C 0.5006(4) 0.2207(3) 0.2715(3) 0.0287(11) Uani 1 d .
H35 H 0.5421 0.2721 0.2681 0.034 Uiso 1 calc R
C36 C 0.4114(4) 0.1970(2) 0.1951(3) 0.0246(10) Uani 1 d .
C37 C 0.3812(5) 0.2521(3) 0.1074(3) 0.0349(12) Uani 1 d .
H37A H 0.3937 0.2223 0.0460 0.052 Uiso 1 calc R
H37B H 0.4376 0.2999 0.1127 0.052 Uiso 1 calc R
H37C H 0.2924 0.2702 0.1063 0.052 Uiso 1 calc R
P1 P 0.24388(12) 0.06110(7) 0.59502(9) 0.0308(3) Uani 1 d .
F1 F 0.2796(3) -0.01078(16) 0.52096(19) 0.0464(7) Uani 1 d .
F2 F 0.2084(3) 0.13307(17) 0.6684(2) 0.0516(8) Uani 1 d .
F3 F 0.3919(3) 0.07465(17) 0.6269(2) 0.0553(8) Uani 1 d .
F4 F 0.2511(3) 0.12591(17) 0.5072(2) 0.0514(8) Uani 1 d .
F5 F 0.0967(3) 0.04749(16) 0.5619(2) 0.0447(7) Uani 1 d .
F6 F 0.2369(3) -0.00407(17) 0.68159(19) 0.0516(8) 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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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_publ_flag
N2 Ir1 N4 84.23(12) . y
N2 Ir1 N1 163.92(13) . y
N4 Ir1 N1 81.01(12) . y
N2 Ir1 C1 85.68(14) . y
N4 Ir1 C1 93.94(15) . y
N1 Ir1 C1 88.96(14) . y
N2 Ir1 N3 84.66(12) . y
N4 Ir1 N3 80.18(12) . y
N1 Ir1 N3 99.03(12) . y
C1 Ir1 N3 169.14(13) . y
N2 Ir1 Cl1 94.54(10) . y
N4 Ir1 Cl1 176.51(9) . y
N1 Ir1 Cl1 99.81(9) . y
C1 Ir1 Cl1 82.70(13) . y
N3 Ir1 Cl1 102.99(9) . y
C1 C1 Ir1 117.7(4) 3 y
C16 N1 C12 118.6(3) . y
C16 N1 Ir1 130.2(3) . y
C12 N1 Ir1 110.5(3) . y
C22 N2 C26 118.9(3) . y
C22 N2 Ir1 113.1(3) . y
C26 N2 Ir1 128.0(3) . y
C32 N3 C36 117.2(3) . y
C32 N3 Ir1 109.1(2) . y
C36 N3 Ir1 132.3(3) . y
C31 N4 C21 112.2(3) . y
C31 N4 C11 107.1(3) . y
C21 N4 C11 112.3(3) . y
C31 N4 Ir1 110.7(2) . y
C21 N4 Ir1 108.6(2) . y
C11 N4 Ir1 105.8(2) . y
N4 C11 C12 109.2(3) . y
N1 C12 C13 121.8(4) . y
N1 C12 C11 116.7(3) . y
C13 C12 C11 121.3(4) . y
C14 C13 C12 118.9(4) . y
C15 C14 C13 119.7(4) . y
C14 C15 C16 120.6(4) . y
N1 C16 C15 119.9(4) . y
N1 C16 C17 119.8(4) . y
C15 C16 C17 120.3(4) . y
N4 C21 C22 111.9(3) . y
N2 C22 C23 121.5(4) . y
N2 C22 C21 117.2(3) . y
C23 C22 C21 121.0(4) . y
C22 C23 C24 119.9(4) . y
C25 C24 C23 118.9(4) . y
C24 C25 C26 119.9(4) . y
N2 C26 C25 120.9(4) . y
C32 C31 N4 112.4(3) . y
N3 C32 C33 123.5(4) . y
N3 C32 C31 116.5(3) . y
C33 C32 C31 119.9(4) . y
C32 C33 C34 118.5(4) . y
C35 C34 C33 119.1(4) . y
C34 C35 C36 120.5(4) . y
N3 C36 C35 121.1(4) . y
N3 C36 C37 118.6(4) . y
C35 C36 C37 120.3(4) . y
F6 P1 F5 90.49(16) . y
F6 P1 F4 179.41(17) . y
F5 P1 F4 89.45(15) . y
F6 P1 F3 89.95(17) . y
F5 P1 F3 179.34(17) . y
F4 P1 F3 90.10(17) . y
F6 P1 F2 90.56(16) . y
F5 P1 F2 90.19(16) . y
F4 P1 F2 90.02(16) . y
F3 P1 F2 90.29(15) . y
F6 P1 F1 89.73(15) . y
F5 P1 F1 89.85(15) . y
F4 P1 F1 89.69(16) . y
F3 P1 F1 89.66(15) . y
F2 P1 F1 179.71(17) . y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N2 2.040(3) . y
Ir1 N4 2.043(3) . y
Ir1 N1 2.087(3) . y
Ir1 C1 2.102(4) . y
Ir1 N3 2.281(3) . y
Ir1 Cl1 2.3787(11) . y
C1 C1 1.518(8) 3 y
N1 C16 1.359(5) . y
N1 C12 1.370(5) . y
N2 C22 1.357(5) . y
N2 C26 1.359(5) . y
N3 C32 1.359(5) . y
N3 C36 1.363(5) . y
N4 C31 1.499(5) . y
N4 C21 1.507(5) . y
N4 C11 1.509(5) . y
C11 C12 1.510(6) . y
C12 C13 1.375(5) . y
C13 C14 1.366(6) . y
C14 C15 1.364(6) . y
C15 C16 1.384(6) . y
C16 C17 1.478(6) . y
C21 C22 1.512(6) . y
C22 C23 1.376(5) . y
C23 C24 1.378(6) . y
C24 C25 1.375(6) . y
C25 C26 1.389(6) . y
C31 C32 1.495(5) . y
C32 C33 1.378(6) . y
C33 C34 1.381(6) . y
C34 C35 1.366(6) . y
C35 C36 1.390(6) . y
C36 C37 1.500(6) . y
P1 F6 1.587(3) . y
P1 F5 1.594(3) . y
P1 F4 1.596(3) . y
P1 F3 1.599(3) . y
P1 F2 1.602(3) . y
P1 F1 1.607(3) . y
