#------------------------------------------------------------------------------
#$Date: 2017-05-04 22:48:54 +0300 (Thu, 04 May 2017) $
#$Revision: 196046 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/72/4087295.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_4087295
loop_
_publ_author_name
'Blaya, María'
'Bautista, Delia'
'Gil-Rubio, Juan'
'Vicente, José'
_publ_section_title
;
 Perfluoroalkylation of Coordinated Ethene in Rh(I) and Ir(I) Complexes.
 Catalytic Addition of Iodoperfluoroalkanes to Ethene
;
_journal_issue                   7
_journal_name_full               Organometallics
_journal_page_first              1245
_journal_paper_doi               10.1021/acs.organomet.6b00929
_journal_volume                  36
_journal_year                    2017
_chemical_formula_sum            'C32 H38 F18 I2 Ir2'
_chemical_formula_weight         1402.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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     Patterson
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.707(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1205(13)
_cell_length_b                   14.3933(15)
_cell_length_c                   11.6847(12)
_cell_measurement_reflns_used    5186
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.25
_cell_volume                     1962.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22952
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.588
_diffrn_reflns_theta_min         1.745
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    8.457
_exptl_absorpt_correction_T_max  0.7284
_exptl_absorpt_correction_T_min  0.4576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.374
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.679
_refine_diff_density_min         -2.460
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.425
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4704
_refine_ls_number_restraints     139
_refine_ls_restrained_S_all      1.406
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0456
_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)+28.2614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4471
_reflns_number_total             4704
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00929_si_002.cif
_cod_data_source_block           mbm892si
_cod_database_code               4087295
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.311
_shelx_estimated_absorpt_t_max   0.728
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.41510(3) 0.92726(2) 0.85470(3) 0.01347(9) Uani 1 1 d . . . . .
I1 I 0.51676(5) 1.09607(3) 0.90625(4) 0.01545(12) Uani 1 1 d . . . . .
C1 C 0.5128(8) 0.8029(6) 0.8142(7) 0.0213(16) Uani 1 1 d . U . . .
C2 C 0.5262(8) 0.8762(6) 0.7414(7) 0.0190(16) Uani 1 1 d . U . . .
C3 C 0.4122(8) 0.9066(6) 0.6712(7) 0.0184(16) Uani 1 1 d . U . . .
C4 C 0.3291(8) 0.8464(6) 0.7005(8) 0.0216(17) Uani 1 1 d . U . . .
C5 C 0.3896(9) 0.7866(6) 0.7930(8) 0.0232(17) Uani 1 1 d . U . . .
C6 C 0.6031(10) 0.7499(7) 0.8985(9) 0.036(2) Uani 1 1 d . U . . .
H6A H 0.6309 0.7003 0.8559 0.055 Uiso 1 1 calc R U . . .
H6B H 0.5719 0.7226 0.9599 0.055 Uiso 1 1 calc R U . . .
H6C H 0.6667 0.7915 0.9357 0.055 Uiso 1 1 calc R U . . .
C7 C 0.6381(8) 0.9160(7) 0.7311(9) 0.031(2) Uani 1 1 d . U . . .
H7A H 0.6950 0.9131 0.8086 0.047 Uiso 1 1 calc R U . . .
H7B H 0.6268 0.9808 0.7049 0.047 Uiso 1 1 calc R U . . .
H7C H 0.6653 0.8799 0.6730 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3888(8) 0.9802(7) 0.5762(8) 0.0249(19) Uani 1 1 d . U . . .
H8A H 0.3968 0.9535 0.5018 0.037 Uiso 1 1 calc R U . . .
H8B H 0.4436 1.0312 0.6008 0.037 Uiso 1 1 calc R U . . .
H8C H 0.3107 1.0040 0.5642 0.037 Uiso 1 1 calc R U . . .
C9 C 0.2053(9) 0.8412(8) 0.6365(9) 0.036(2) Uani 1 1 d . U . . .
H9A H 0.1918 0.7878 0.5824 0.053 Uiso 1 1 calc R U . . .
H9B H 0.1820 0.8983 0.5908 0.053 Uiso 1 1 calc R U . . .
H9C H 0.1604 0.8339 0.6942 0.053 Uiso 1 1 calc R U . . .
C10 C 0.3352(11) 0.7112(7) 0.8468(10) 0.041(3) Uani 1 1 d . U . . .
H10A H 0.2604 0.7323 0.8537 0.061 Uiso 1 1 calc R U . . .
H10B H 0.3845 0.6960 0.9259 0.061 Uiso 1 1 calc R U . . .
H10C H 0.3251 0.6559 0.7961 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2584(8) 0.9867(6) 0.8803(8) 0.0212(18) Uani 1 1 d . U . . .
H11A H 0.2029 0.9364 0.8814 0.025 Uiso 1 1 calc R U . . .
H11B H 0.2756 1.0194 0.9576 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2066(8) 1.0541(6) 0.7808(8) 0.0237(17) Uani 1 1 d . U . . .
H12A H 0.2019 1.0222 0.7046 0.028 Uiso 1 1 calc R U . . .
H12B H 0.2607 1.1065 0.7869 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0849(8) 1.0961(7) 0.7735(8) 0.0253(15) Uani 1 1 d D U . . .
C14 C 0.0804(16) 1.1332(13) 0.8978(13) 0.045(5) Uani 0.514(11) 1 d D U P A 1
F1 F 0.0674(12) 1.0644(12) 0.9693(11) 0.064(5) Uani 0.514(11) 1 d D U P A 1
F2 F 0.1756(11) 1.1796(10) 0.9498(13) 0.061(5) Uani 0.514(11) 1 d D U P A 1
F3 F -0.0087(15) 1.191(2) 0.886(4) 0.065(9) Uani 0.514(11) 1 d D U P A 1
C15 C -0.015(2) 1.0261(16) 0.7276(18) 0.039(5) Uani 0.514(11) 1 d D U P A 1
F4 F 0.0088(11) 0.9467(10) 0.7893(14) 0.045(4) Uani 0.514(11) 1 d D U P A 1
F5 F -0.115(3) 1.057(3) 0.745(3) 0.051(7) Uani 0.514(11) 1 d D U P A 1
F6 F -0.0322(12) 1.0104(10) 0.6156(11) 0.049(4) Uani 0.514(11) 1 d D U P A 1
C16 C 0.061(2) 1.1827(13) 0.691(2) 0.038(4) Uani 0.514(11) 1 d D U P A 1
F7 F -0.0472(18) 1.210(3) 0.659(4) 0.053(9) Uani 0.514(11) 1 d D U P A 1
F8 F 0.0863(13) 1.1560(11) 0.5855(12) 0.045(4) Uani 0.514(11) 1 d D U P A 1
F9 F 0.1270(12) 1.2527(9) 0.7301(15) 0.053(4) Uani 0.514(11) 1 d D U P A 1
C14' C 0.0857(17) 1.1590(12) 0.8794(15) 0.027(4) Uani 0.486(11) 1 d D U P A 2
F1' F 0.1379(11) 1.1185(9) 0.9825(10) 0.031(3) Uani 0.486(11) 1 d D U P A 2
F2' F 0.1431(12) 1.2369(9) 0.8705(13) 0.045(4) Uani 0.486(11) 1 d D U P A 2
F3' F -0.0191(16) 1.184(2) 0.886(4) 0.049(7) Uani 0.486(11) 1 d D U P A 2
C15' C -0.002(2) 1.0145(14) 0.763(2) 0.032(4) Uani 0.486(11) 1 d D U P A 2
F4' F 0.0042(11) 0.9828(10) 0.8721(13) 0.044(4) Uani 0.486(11) 1 d D U P A 2
F5' F -0.110(3) 1.047(3) 0.720(3) 0.048(6) Uani 0.486(11) 1 d D U P A 2
F6' F 0.0106(10) 0.9457(9) 0.6958(13) 0.039(4) Uani 0.486(11) 1 d D U P A 2
C16' C 0.0544(17) 1.1547(18) 0.6613(18) 0.031(4) Uani 0.486(11) 1 d D U P A 2
F7' F -0.0388(16) 1.207(3) 0.646(4) 0.031(5) Uani 0.486(11) 1 d D U P A 2
F8' F 0.0254(13) 1.0930(12) 0.5644(10) 0.048(4) Uani 0.486(11) 1 d D U P A 2
F9' F 0.1369(11) 1.2056(11) 0.6446(14) 0.043(4) Uani 0.486(11) 1 d D U P A 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 Ir1 C3 64.7(3) . .
C5 Ir1 C4 38.6(4) . .
C3 Ir1 C4 38.9(3) . .
C5 Ir1 C11 111.4(4) . .
C3 Ir1 C11 114.3(3) . .
C4 Ir1 C11 94.8(3) . .
C5 Ir1 C2 63.2(3) . .
C3 Ir1 C2 38.9(3) . .
C4 Ir1 C2 64.2(3) . .
C11 Ir1 C2 153.1(3) . .
C5 Ir1 C1 38.7(4) . .
C3 Ir1 C1 63.4(3) . .
C4 Ir1 C1 64.0(3) . .
C11 Ir1 C1 149.8(3) . .
C2 Ir1 C1 35.9(3) . .
C5 Ir1 I1 101.9(2) . 3_677
C3 Ir1 I1 157.9(2) . 3_677
C4 Ir1 I1 137.4(2) . 3_677
C11 Ir1 I1 86.6(2) . 3_677
C2 Ir1 I1 120.1(2) . 3_677
C1 Ir1 I1 95.0(2) . 3_677
C5 Ir1 I1 159.2(3) . .
C3 Ir1 I1 103.2(2) . .
C4 Ir1 I1 138.9(2) . .
C11 Ir1 I1 88.8(2) . .
C2 Ir1 I1 96.6(2) . .
C1 Ir1 I1 121.4(2) . .
I1 Ir1 I1 83.624(18) 3_677 .
Ir1 I1 Ir1 96.378(17) 3_677 .
C2 C1 C5 107.5(8) . .
C2 C1 C6 127.8(10) . .
C5 C1 C6 124.7(9) . .
C2 C1 Ir1 71.5(5) . .
C5 C1 Ir1 66.1(5) . .
C6 C1 Ir1 127.3(6) . .
C1 C2 C3 108.6(8) . .
C1 C2 C7 126.4(9) . .
C3 C2 C7 125.0(8) . .
C1 C2 Ir1 72.6(5) . .
C3 C2 Ir1 67.0(4) . .
C7 C2 Ir1 128.2(6) . .
C4 C3 C2 107.5(7) . .
C4 C3 C8 126.5(8) . .
C2 C3 C8 125.6(8) . .
C4 C3 Ir1 70.7(5) . .
C2 C3 Ir1 74.1(4) . .
C8 C3 Ir1 125.8(6) . .
C5 C4 C3 107.2(8) . .
C5 C4 C9 126.5(9) . .
C3 C4 C9 126.0(9) . .
C5 C4 Ir1 70.0(5) . .
C3 C4 Ir1 70.3(4) . .
C9 C4 Ir1 129.8(7) . .
C4 C5 C1 108.9(8) . .
C4 C5 C10 124.4(10) . .
C1 C5 C10 126.2(9) . .
C4 C5 Ir1 71.4(5) . .
C1 C5 Ir1 75.2(5) . .
C10 C5 Ir1 125.8(6) . .
C12 C11 Ir1 110.0(6) . .
C11 C12 C13 118.4(8) . .
C16' C13 C14' 108.4(13) . .
C16 C13 C15 108.1(13) . .
C16' C13 C15' 110.4(13) . .
C14' C13 C15' 111.6(12) . .
C16 C13 C14 104.7(12) . .
C15 C13 C14 108.7(11) . .
C16' C13 C12 105.4(10) . .
C14' C13 C12 112.5(10) . .
C16 C13 C12 110.8(11) . .
C15 C13 C12 113.7(12) . .
C15' C13 C12 108.4(10) . .
C14 C13 C12 110.4(10) . .
F2 C14 F1 108.8(13) . .
F2 C14 F3 108.1(14) . .
F1 C14 F3 107.4(14) . .
F2 C14 C13 110.6(14) . .
F1 C14 C13 111.7(13) . .
F3 C14 C13 110(3) . .
F6 C15 F4 110.4(18) . .
F6 C15 F5 107.7(19) . .
F4 C15 F5 106.0(19) . .
F6 C15 C13 110.9(15) . .
F4 C15 C13 109.3(17) . .
F5 C15 C13 112(3) . .
F9 C16 F7 110(2) . .
F9 C16 F8 105.4(16) . .
F7 C16 F8 105(2) . .
F9 C16 C13 114.5(17) . .
F7 C16 C13 115(3) . .
F8 C16 C13 106.1(15) . .
F1' C14' F2' 107.9(14) . .
F1' C14' F3' 106.7(16) . .
F2' C14' F3' 107.7(17) . .
F1' C14' C13 111.7(15) . .
F2' C14' C13 108.8(15) . .
F3' C14' C13 114(2) . .
F6' C15' F4' 109.3(19) . .
F6' C15' F5' 107(2) . .
F4' C15' F5' 105(2) . .
F6' C15' C13 116.1(18) . .
F4' C15' C13 108.6(15) . .
F5' C15' C13 110(3) . .
F9' C16' F7' 109(2) . .
F9' C16' F8' 105.6(17) . .
F7' C16' F8' 103.4(18) . .
F9' C16' C13 115.2(16) . .
F7' C16' C13 116(2) . .
F8' C16' C13 107.1(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C5 2.143(8) .
Ir1 C3 2.156(8) .
Ir1 C4 2.161(8) .
Ir1 C11 2.176(9) .
Ir1 C2 2.252(8) .
Ir1 C1 2.266(8) .
Ir1 I1 2.7107(6) 3_677
Ir1 I1 2.7171(6) .
I1 Ir1 2.7107(6) 3_677
C1 C2 1.393(12) .
C1 C5 1.465(14) .
C1 C6 1.472(13) .
C2 C3 1.470(12) .
C2 C7 1.507(13) .
C3 C4 1.438(12) .
C3 C8 1.505(12) .
C4 C5 1.421(13) .
C4 C9 1.486(13) .
C5 C10 1.494(13) .
C11 C12 1.514(12) .
C12 C13 1.574(13) .
C13 C16' 1.52(2) .
C13 C14' 1.53(2) .
C13 C16 1.554(15) .
C13 C15 1.557(16) .
C13 C15' 1.56(2) .
C13 C14 1.563(15) .
C14 F2 1.330(14) .
C14 F1 1.333(14) .
C14 F3 1.341(14) .
C15 F6 1.29(2) .
C15 F4 1.34(2) .
C15 F5 1.36(2) .
C16 F9 1.29(2) .
C16 F7 1.326(18) .
C16 F8 1.40(2) .
C14' F1' 1.334(13) .
C14' F2' 1.338(14) .
C14' F3' 1.341(14) .
C15' F6' 1.30(2) .
C15' F4' 1.34(2) .
C15' F5' 1.36(2) .
C16' F9' 1.30(2) .
C16' F7' 1.330(19) .
C16' F8' 1.41(2) .
