Iridium Complexes of the Conformationally Rigid IBioxMe4 Ligand: Hydride Complexes and Dehydrogenation of Cyclooctene
Hauser, Simone A.; Tonner, Ralf; Chaplin, Adrian B.; Organometallics 34 (2015) 4419–; doi:10.1021/acs.organomet.5b00658

data_4087866
_publ_section_title
;
 Iridium Complexes of the Conformationally Rigid IBioxMe4 Ligand: Hydride
 Complexes and Dehydrogenation of Cyclooctene
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4419
_journal_paper_doi               10.1021/acs.organomet.5b00658
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C44 H64 Cl Ir2 N8 O8, C32 H12 B F24'
_chemical_formula_sum            'C76 H80 B Cl F24 Ir2 N8 O8'
_chemical_formula_weight         2120.14
_chemical_melting_point          ?
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4554(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.50552(17)
_cell_length_b                   22.2205(3)
_cell_length_c                   30.8469(5)
_cell_measurement_reflns_used    29932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.0960
_cell_measurement_theta_min      3.4060
_cell_volume                     9156.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -10.00   98.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       22.1076   77.0000   60.0000 108

  2 omega  -10.00   98.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       22.1076   77.0000 -180.0000 108

  3 omega  -10.00   98.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       22.1076   77.0000   30.0000 108

  4 omega  -56.00   53.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.0451   77.0000 -150.0000 109

  5 omega  -25.00   63.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       22.1076  -99.0000  -60.0000 88

  6 omega   35.00  111.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       22.1076  178.0000   60.0000 76

  7 omega  -52.00  -27.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       22.1076  -38.0000   60.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0407434000
_diffrn_orient_matrix_UB_12      0.0203811000
_diffrn_orient_matrix_UB_13      0.0013012000
_diffrn_orient_matrix_UB_21      0.0004198000
_diffrn_orient_matrix_UB_22      -0.0031531000
_diffrn_orient_matrix_UB_23      -0.0228546000
_diffrn_orient_matrix_UB_31      -0.0340332000
_diffrn_orient_matrix_UB_32      0.0243678000
_diffrn_orient_matrix_UB_33      -0.0040539000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            133044
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.102
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         3.168
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4192
_exptl_crystal_recrystallization_method
'Crystals grown from C6H4F2-heptane at 253 K'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
)
TITL 0082abc14
CELL   13.5055   22.2206   30.8469     90.00     98.46     90.00
SPGR P21/c
C101 0.639 0.937 0.202 !       6.64 eA-3
C102 0.705 0.329 0.756 !       5.64 eA-3
C103 0.280 0.669 0.201 !       5.42 eA-3
C104 0.240 0.815 0.703 !       5.25 eA-3
C105 0.281 0.827 0.706 !       4.81 eA-3
C106 0.690 0.553 0.701 !       4.74 eA-3
C107 0.413 0.023 0.765 !       4.66 eA-3
C108 0.578 0.946 0.236 !       4.60 eA-3
C109 0.300 0.795 0.752 !       4.58 eA-3
C110 0.671 0.905 0.215 !       4.41 eA-3
C111 0.447 0.970 0.761 !       4.41 eA-3
C112 0.393 0.045 0.774 !       4.36 eA-3
C113 0.612 0.469 0.711 !       4.29 eA-3
C114 0.347 0.933 0.757 !       4.29 eA-3
C115 0.407 0.634 0.256 !       4.28 eA-3
Q116 0.816 0.794 0.536 !       4.25 eA-3
C117 0.465 0.493 0.259 !       4.24 eA-3
C118 0.277 0.829 0.757 !       4.19 eA-3
C119 0.356 0.006 0.804 !       4.19 eA-3
C120 0.612 0.064 0.222 !       4.17 eA-3
C121 0.411 0.868 0.759 !       4.15 eA-3
C122 0.326 0.676 0.255 !       4.12 eA-3
C123 0.608 0.177 0.233 !       4.12 eA-3
C124 0.374 0.602 0.255 !       4.11 eA-3
C125 0.348 0.531 0.302 !       3.98 eA-3
C126 0.439 0.601 0.258 !       3.87 eA-3
C127 0.392 0.907 0.764 !       3.83 eA-3
C128 0.635 0.409 0.726 !       3.81 eA-3
C129 0.655 0.522 0.712 !       3.68 eA-3
C130 0.346 0.969 0.806 !       3.64 eA-3
C131 0.598 0.500 0.706 !       3.58 eA-3
C132 0.646 0.310 0.759 !       3.57 eA-3
C133 0.354 0.918 0.782 !       3.53 eA-3
C134 0.596 0.572 0.711 !       3.41 eA-3
Q135 0.422 0.656 0.268 !       3.41 eA-3
C136 0.766 0.288 0.793 !       3.39 eA-3
C137 0.364 0.016 0.773 !       3.37 eA-3
C138 0.481 0.945 0.751 !       3.34 eA-3
C139 0.541 0.515 0.727 !       3.28 eA-3
C140 0.440 0.929 0.762 !       3.26 eA-3
C141 0.390 0.086 0.797 !       3.13 eA-3
C142 0.324 0.560 0.297 !       3.12 eA-3
C143 0.347 0.071 0.815 !       3.06 eA-3
C144 0.276 0.809 0.726 !       3.05 eA-3
C145 0.607 0.413 0.753 !       3.05 eA-3
C146 0.402 0.055 0.796 !       2.99 eA-3
C147 0.370 0.859 0.767 !       2.97 eA-3
C148 0.375 0.834 0.751 !       2.95 eA-3
C149 0.308 0.861 0.768 !       2.91 eA-3
C150 0.703 0.149 0.290 !       2.90 eA-3
C151 0.692 0.345 0.719 !       2.82 eA-3
C152 0.637 0.392 0.702 !       2.81 eA-3
C153 0.564 0.051 0.224 !       2.80 eA-3
C154 0.754 0.307 0.760 !       2.76 eA-3
C155 0.302 0.703 0.274 !       2.75 eA-3
C156 0.651 0.208 0.226 !       2.72 eA-3
C157 0.599 0.115 0.272 !       2.71 eA-3
C158 0.439 0.013 0.789 !       2.68 eA-3
C159 0.639 0.350 0.718 !       2.68 eA-3
C160 0.503 0.517 0.240 !       2.65 eA-3
C161 0.685 0.343 0.796 !       2.64 eA-3
C162 0.421 0.039 0.741 !       2.63 eA-3
C163 0.640 0.374 0.759 !       2.62 eA-3
C164 0.735 0.443 0.656 !       2.57 eA-3
C165 0.297 0.469 0.305 !       2.54 eA-3
C166 0.578 0.515 0.753 !       2.54 eA-3
C167 0.369 0.875 0.785 !       2.53 eA-3
Q168 0.829 0.922 0.026 !       2.44 eA-3
Q169 0.216 0.770 0.721 !       2.42 eA-3
C170 0.549 0.572 0.765 !       2.41 eA-3
C171 0.464 0.471 0.278 !       2.41 eA-3
C172 0.614 0.044 0.242 !       2.38 eA-3
Q173 0.158 0.689 0.205 !       2.32 eA-3
Q174 0.433 0.131 0.281 !       2.32 eA-3
C175 0.693 0.394 0.720 !       2.31 eA-3
Q176 0.222 0.912 0.845 !       2.31 eA-3
Q177 0.228 0.411 0.304 !       2.29 eA-3
C178 0.719 0.219 0.272 !       2.27 eA-3
C179 0.320 0.632 0.289 !       2.26 eA-3
C180 0.319 0.867 0.790 !       2.26 eA-3
C181 0.331 0.978 0.788 !       2.26 eA-3
C182 0.224 0.378 0.282 !       2.24 eA-3
C183 0.327 0.683 0.202 !       2.23 eA-3
C184 0.295 0.408 0.312 !       2.21 eA-3
C185 0.422 0.016 0.806 !       2.20 eA-3
Q186 0.169 0.078 0.974 !       2.20 eA-3
C187 0.407 0.076 0.773 !       2.15 eA-3
C188 0.709 0.163 0.314 !       2.13 eA-3
C189 0.467 0.579 0.283 !       2.12 eA-3
C190 0.533 0.116 0.274 !       2.12 eA-3
C191 0.362 0.813 0.783 !       2.11 eA-3
Q192 0.192 0.592 0.164 !       2.11 eA-3
Q193 0.721 0.273 0.706 !       2.08 eA-3
Q194 0.051 0.928 0.530 !       2.08 eA-3
C195 0.346 0.017 0.749 !       2.08 eA-3
C196 0.420 0.543 0.235 !       2.06 eA-3
Q197 0.238 0.742 0.703 !       2.06 eA-3
C198 0.653 0.498 0.719 !       2.06 eA-3
C199 0.369 0.015 0.729 !       2.05 eA-3
)
;
_refine_diff_density_max         1.555
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1201
_refine_ls_number_reflns         20182
_refine_ls_number_restraints     708
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+11.1141P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15277
_reflns_number_total             20182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00658_si_003.cif
_cod_data_source_block           0082abc14
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4087866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23A-C30A \\sim C23A-C130 \\sim C29A-C23A \\sim C23A-C129
 with sigma of 0.01
 O28-C127 \\sim O28-C27 \\sim O25A-C124 \\sim O25A-C24A
 with sigma of 0.01
 C127-C26 \\sim C27-C26 \\sim C23A-C124 \\sim C24A-C23A
 with sigma of 0.01
 C30A-C29A \\sim C130-C129
 with sigma of 0.01
 C223-F13 \\sim C223-F14 \\sim C223-F15 \\sim C223-F13A \\sim C223-F14A \\sim
C223-F15A
 with sigma of 0.01
 F13-F14 \\sim F14-F15 \\sim F15-F13 \\sim F13A-F14A \\sim F14A-F15A \\sim
F15A-F13A
 with sigma of 0.01
 C219-F13 \\sim C219-F14 \\sim C219-F15 \\sim C219-F13A \\sim C219-F14A \\sim
C219-F15A
 with sigma of 0.01
 C316-F10A \\sim C316-F11A \\sim C316-F12A \\sim C216-F10 \\sim C216-F11 \\sim
C216-F12
 with sigma of 0.01
 F10A-F11A \\sim F11A-F12A \\sim F12A-F10A \\sim F10-F11 \\sim F11-F12 \\sim
F12-F10
 with sigma of 0.01
 C213-F10A \\sim C213-F11A \\sim C213-F12A \\sim C213-F10 \\sim C213-F11 \\sim
C213-F12
 with sigma of 0.01
 C213-C316 \\sim C213-C216
 with sigma of 0.01
 C207-F1 \\sim C207-F2 \\sim C207-F3 \\sim C307-F1A \\sim C307-F2A \\sim
C307-F3A
 with sigma of 0.01
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.01
 C203-F1 \\sim C203-F2 \\sim C203-F3 \\sim C203-F1A \\sim C203-F2A \\sim
C203-F3A
 with sigma of 0.01
 C203-C207 \\sim C203-C307
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C27 \\sim C127 \\sim C124 \\sim C24A \\sim C30A \\sim C130 \\sim C29A \\sim
C129 \\sim C307 \\sim C207 \\sim C316 \\sim C216 \\sim F1 \\sim F1A \\sim F2
\\sim F2A \\sim F3 \\sim F3A \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim
F9 \\sim F10 \\sim F10A \\sim F11 \\sim F11A \\sim F12 \\sim F12A \\sim F13
\\sim F13A \\sim F14 \\sim F14A \\sim F15 \\sim F15A \\sim F16 \\sim F17 \\sim
F18 \\sim F19 \\sim F20 \\sim F21 \\sim F22 \\sim F23 \\sim F24: within 1.7A
with sigma of 0.007 and sigma for terminal atoms of 0.02
Uanis(C27) \\sim Ueq, Uanis(C127) \\sim Ueq, Uanis(C124) \\sim Ueq, Uanis(C24A)
\\sim Ueq, Uanis(C30A) \\sim Ueq, Uanis(C130) \\sim Ueq, Uanis(C29A) \\sim Ueq,
Uanis(C129) \\sim Ueq, Uanis(C307) \\sim Ueq, Uanis(C207) \\sim Ueq,
Uanis(C316) \\sim Ueq, Uanis(C216) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3) \\sim Ueq,
Uanis(F3A) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim
Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F10)
\\sim Ueq, Uanis(F10A) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F11A) \\sim Ueq,
Uanis(F12) \\sim Ueq, Uanis(F12A) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F13A)
\\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F14A) \\sim Ueq, Uanis(F15) \\sim Ueq,
Uanis(F15A) \\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F18)
\\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F21) \\sim Ueq,
Uanis(F22) \\sim Ueq, Uanis(F23) \\sim Ueq, Uanis(F24) \\sim Ueq: with sigma of
0.007 and sigma for terminal atoms of 0.02
Uanis(C124) = Uanis(C24A)
Uanis(C27) = Uanis(C127)
Uanis(C30A) = Uanis(C130)
Uanis(C29A) = Uanis(C129)
Uanis(C316) = Uanis(C216)
Uanis(C307) = Uanis(C207)
4. Others
 Sof(C124)=Sof(H12E)=Sof(H12F)=Sof(C129)=Sof(H12I)=Sof(H12J)=Sof(H12K)=
 Sof(C130)=Sof(H13A)=Sof(H13B)=Sof(H13C)=1-FVAR(1)
 Sof(C24A)=Sof(H24C)=Sof(H24D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=
 Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=FVAR(1)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=Sof(C316)=1-FVAR(2)
 Sof(F10)=Sof(F11)=Sof(F12)=Sof(C216)=FVAR(2)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C307)=1-FVAR(3)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C207)=FVAR(3)
 Fixed Sof: C27(0.5) H27A(0.5) H27B(0.5) C127(0.5) H12G(0.5) H12H(0.5)
 F13(0.5) F13A(0.5) F14(0.5) F14A(0.5) F15(0.5) F15A(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C12(H12A,H12B), C12A(H12C,H12D), C24(H24A,H24B),
 C24A(H24C,H24D), C27(H27A,H27B), C27A(H27C,H27D), C124(H12E,H12F), C127(H12G,
 H12H)
5.b Aromatic/amide H refined with riding coordinates:
 C202(H202), C204(H204), C206(H206), C210(H210), C212(H212), C214(H214),
 C218(H218), C220(H220), C222(H222), C226(H226), C228(H228), C230(H230)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F), C15(H15A,H15B,H15C), C15A(H15D,
 H15E,H15F), C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F), C17(H17A,H17B,H17C),
 C17A(H17D,H17E,H17F), C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F), C30(H30A,H30B,
 H30C), C30A(H30D,H30E,H30F), C31(H31A,H31B,H31C), C31A(H31D,H31E,H31F),
 C32(H32A,H32B,H32C), C32A(H32D,H32E,H32F), C129(H12I,H12J,H12K), C130(H13A,
 H13B,H13C)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'