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_4087868
_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         'C33 H48 Ir N6 O6, C6 H4 F2, C32 H12 B F24'
_chemical_formula_sum            'C71 H66 B F26 Ir N6 O6'
_chemical_formula_weight         1796.30
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                99.7323(12)
_cell_angle_beta                 99.5664(14)
_cell_angle_gamma                100.4143(12)
_cell_formula_units_Z            4
_cell_length_a                   18.2120(3)
_cell_length_b                   19.9992(2)
_cell_length_c                   20.9223(3)
_cell_measurement_reflns_used    37277
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.6950
_cell_measurement_theta_min      2.9800
_cell_volume                     7233.28(18)
_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      293(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   19.00   44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3155  -38.0000  150.0000 25

  2 omega  -59.00  -30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3155  -38.0000  150.0000 29

  3 omega   14.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3155   38.0000   60.0000 79

  4 omega  -52.00   44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3155  -38.0000 -120.0000 96

  5 omega   35.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3155  178.0000  -90.0000 46

  6 omega -104.00  -59.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.2530 -178.0000  -30.0000 45

  7 omega -108.00  -83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.2530 -178.0000    0.0000 25

  8 omega  -37.00    5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.2530  -57.0000   60.0000 42

  9 omega  -23.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.2530  -99.0000  -60.0000 47

 10 omega -107.00  -78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.2530 -178.0000  120.0000 29

 11 omega   -9.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3155   38.0000  -90.0000 47
;
_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      0.0185289000
_diffrn_orient_matrix_UB_12      -0.0009925000
_diffrn_orient_matrix_UB_13      -0.0272979000
_diffrn_orient_matrix_UB_21      -0.0357778000
_diffrn_orient_matrix_UB_22      -0.0059292000
_diffrn_orient_matrix_UB_23      -0.0219054000
_diffrn_orient_matrix_UB_31      0.0034788000
_diffrn_orient_matrix_UB_32      0.0363513000
_diffrn_orient_matrix_UB_33      0.0029905000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            87194
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.103
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.976
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79397
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3592
_exptl_crystal_recrystallization_method
'Crystals grown from C6H4F2-heptane at 278 K'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2191
_refine_ls_number_reflns         31874
_refine_ls_number_restraints     1092
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+4.7347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                26299
_reflns_number_total             31874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00658_si_003.cif
_cod_data_source_block           0057abc14
_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_original_cell_volume        7233.26(19)
_cod_database_code               4087868
_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
 C408-F404 \\sim C408-F405 \\sim C408-F406 \\sim C408-F504 \\sim C408-F505
\\sim C408-F506
 with sigma of 0.01
 F404-F405 \\sim F405-F406 \\sim F406-F404 \\sim F504-F505 \\sim F505-F506
\\sim F506-F504
 with sigma of 0.01
 C405-F404 \\sim C405-F405 \\sim C405-F406 \\sim C405-F504 \\sim C405-F505
\\sim C405-F506
 with sigma of 0.01
 C424-F416 \\sim C424-F417 \\sim C424-F418 \\sim C424-F516 \\sim C424-F517
\\sim C424-F518
 with sigma of 0.01
 F416-F417 \\sim F417-F418 \\sim F418-F416 \\sim F516-F517 \\sim F517-F518
\\sim F518-F516
 with sigma of 0.01
 C421-F416 \\sim C421-F417 \\sim C421-F418 \\sim C421-F516 \\sim C421-F517
\\sim C421-F518
 with sigma of 0.01
 C432-F422 \\sim C432-F423 \\sim C432-F424 \\sim C432-F522 \\sim C432-F523
\\sim C432-F524
 with sigma of 0.01
 F422-F423 \\sim F423-F424 \\sim F424-F422 \\sim F522-F523 \\sim F523-F524
\\sim F524-F522
 with sigma of 0.01
 C429-F422 \\sim C429-F423 \\sim C429-F424 \\sim C429-F522 \\sim C429-F523
\\sim C429-F524
 with sigma of 0.01
 C207-F201 \\sim C207-F202 \\sim C207-F203 \\sim C207-F301 \\sim C207-F302
\\sim C207-F303
 with sigma of 0.01
 F201-F202 \\sim F202-F203 \\sim F203-F201 \\sim F301-F302 \\sim F302-F303
\\sim F303-F301
 with sigma of 0.01
 C203-F201 \\sim C203-F202 \\sim C203-F203 \\sim C203-F301 \\sim C203-F302
\\sim C203-F303
 with sigma of 0.01
 C224-F216 \\sim C224-F217 \\sim C224-F218 \\sim C224-F316 \\sim C224-F317
\\sim C224-F318
 with sigma of 0.01
 F216-F217 \\sim F217-F218 \\sim F218-F216 \\sim F316-F317 \\sim F317-F318
\\sim F318-F316
 with sigma of 0.01
 C221-F216 \\sim C221-F217 \\sim C221-F218 \\sim C221-F316 \\sim C221-F317
\\sim C221-F318
 with sigma of 0.01
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.01
 C10A-C16A \\sim C10A-C16B \\sim C15A-C10A \\sim C15B-C10A
 with sigma of 0.01
 C11B-C10A \\sim C11A-C10A
 with sigma of 0.01
 O12A-C11B \\sim O12A-C11A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C30 \\sim C31 \\sim C25 \\sim C26 \\sim O27 \\sim C20 \\sim N21 \\sim C17 \\sim
N18 \\sim C19 \\sim O24 \\sim C23 \\sim C28 \\sim C22 \\sim C29 \\sim C16A
\\sim C16B \\sim C10A \\sim C15A \\sim C15B \\sim C11B \\sim C11A \\sim O12A
\\sim F907 \\sim F908 \\sim F401 \\sim F402 \\sim F403 \\sim F404 \\sim F405
\\sim F406 \\sim F407 \\sim F408 \\sim F409 \\sim F410 \\sim F411 \\sim F412
\\sim F413 \\sim F414 \\sim F415 \\sim F416 \\sim F417 \\sim F418 \\sim F419
\\sim F420 \\sim F421 \\sim F422 \\sim F423 \\sim F424 \\sim F504 \\sim F505
\\sim F506 \\sim F516 \\sim F517 \\sim F518 \\sim F522 \\sim F523 \\sim F524
\\sim F201 \\sim F202 \\sim F203 \\sim F204 \\sim F205 \\sim F206 \\sim F207
\\sim F208 \\sim F209 \\sim F210 \\sim F211 \\sim F212 \\sim F213 \\sim F214
\\sim F215 \\sim F216 \\sim F217 \\sim F218 \\sim F219 \\sim F220 \\sim F221
\\sim F222 \\sim F223 \\sim F224 \\sim F301 \\sim F302 \\sim F303 \\sim F316
\\sim F317 \\sim F318 \\sim F915 \\sim F916: within 1.7A with sigma of 0.005
and sigma for terminal atoms of 0.02
Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26)
\\sim Ueq, Uanis(O27) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(N21) \\sim Ueq,
Uanis(C17) \\sim Ueq, Uanis(N18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(O24)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C16B) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C15B) \\sim Ueq, Uanis(C11B) \\sim Ueq,
Uanis(C11A) \\sim Ueq, Uanis(O12A) \\sim Ueq, Uanis(F907) \\sim Ueq,
Uanis(F908) \\sim Ueq, Uanis(F401) \\sim Ueq, Uanis(F402) \\sim Ueq,
Uanis(F403) \\sim Ueq, Uanis(F404) \\sim Ueq, Uanis(F405) \\sim Ueq,
Uanis(F406) \\sim Ueq, Uanis(F407) \\sim Ueq, Uanis(F408) \\sim Ueq,
Uanis(F409) \\sim Ueq, Uanis(F410) \\sim Ueq, Uanis(F411) \\sim Ueq,
Uanis(F412) \\sim Ueq, Uanis(F413) \\sim Ueq, Uanis(F414) \\sim Ueq,
Uanis(F415) \\sim Ueq, Uanis(F416) \\sim Ueq, Uanis(F417) \\sim Ueq,
Uanis(F418) \\sim Ueq, Uanis(F419) \\sim Ueq, Uanis(F420) \\sim Ueq,
Uanis(F421) \\sim Ueq, Uanis(F422) \\sim Ueq, Uanis(F423) \\sim Ueq,
Uanis(F424) \\sim Ueq, Uanis(F504) \\sim Ueq, Uanis(F505) \\sim Ueq,
Uanis(F506) \\sim Ueq, Uanis(F516) \\sim Ueq, Uanis(F517) \\sim Ueq,
Uanis(F518) \\sim Ueq, Uanis(F522) \\sim Ueq, Uanis(F523) \\sim Ueq,
Uanis(F524) \\sim Ueq, Uanis(F201) \\sim Ueq, Uanis(F202) \\sim Ueq,
Uanis(F203) \\sim Ueq, Uanis(F204) \\sim Ueq, Uanis(F205) \\sim Ueq,
Uanis(F206) \\sim Ueq, Uanis(F207) \\sim Ueq, Uanis(F208) \\sim Ueq,
Uanis(F209) \\sim Ueq, Uanis(F210) \\sim Ueq, Uanis(F211) \\sim Ueq,
Uanis(F212) \\sim Ueq, Uanis(F213) \\sim Ueq, Uanis(F214) \\sim Ueq,
Uanis(F215) \\sim Ueq, Uanis(F216) \\sim Ueq, Uanis(F217) \\sim Ueq,
Uanis(F218) \\sim Ueq, Uanis(F219) \\sim Ueq, Uanis(F220) \\sim Ueq,
Uanis(F221) \\sim Ueq, Uanis(F222) \\sim Ueq, Uanis(F223) \\sim Ueq,
Uanis(F224) \\sim Ueq, Uanis(F301) \\sim Ueq, Uanis(F302) \\sim Ueq,
Uanis(F303) \\sim Ueq, Uanis(F316) \\sim Ueq, Uanis(F317) \\sim Ueq,
Uanis(F318) \\sim Ueq, Uanis(F915) \\sim Ueq, Uanis(F916) \\sim Ueq: with sigma
of 0.004 and sigma for terminal atoms of 0.008
4. Others
 Sof(C11B)=Sof(H11C)=Sof(H11D)=Sof(C15B)=Sof(H15D)=Sof(H15E)=Sof(H15F)=
 Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
 Sof(F522)=Sof(F523)=Sof(F524)=1-FVAR(2)
 Sof(F422)=Sof(F423)=Sof(F424)=FVAR(2)
 Sof(F504)=Sof(F505)=Sof(F506)=1-FVAR(3)
 Sof(F404)=Sof(F405)=Sof(F406)=FVAR(3)
 Sof(F516)=Sof(F517)=Sof(F518)=1-FVAR(4)
 Sof(F416)=Sof(F417)=Sof(F418)=FVAR(4)
 Fixed Sof: F201(0.5) F202(0.5) F203(0.5) F216(0.5) F217(0.5) F218(0.5)
 F301(0.5) F302(0.5) F303(0.5) F316(0.5) F317(0.5) F318(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11E,H11F), C23(H23C,H23D), C26(H26C,H26D), C38(H38C,H38D),
 C41(H41C,H41D), C8A(H8AA,H8AB), C11A(H11A,H11B), C11B(H11C,H11D), C23A(H23A,
 H23B), C26A(H26A,H26B), C38A(H38A,H38B), C41A(H41A,H41B)
5.b Aromatic/amide H refined with riding coordinates:
 C903(H903), C904(H904), C905(H905), C906(H906), C402(H402), C404(H404),
 C406(H406), C410(H410), C412(H412), C414(H414), C418(H418), C420(H420),
 C422(H422), C426(H426), C428(H428), C430(H430), C202(H202), C204(H204),
 C206(H206), C210(H210), C212(H212), C214(H214), C218(H218), C220(H220),
 C222(H222), C226(H226), C228(H228), C230(H230), C911(H911), C912(H912),
 C913(H913), C914(H914)
5.c Idealised Me refined as rotating group:
 C13(H13D,H13E,H13F), C14(H14D,H14E,H14F), C15(H15G,H15H,H15I), C16(H16G,H16H,
 H16I), C28(H28D,H28E,H28F), C29(H29D,H29E,H29F), C30(H30D,H30E,H30F), C31(H31D,
 H31E,H31F), C43(H43D,H43E,H43F), C44(H44D,H44E,H44F), C45(H45D,H45E,H45F),
 C46(H46D,H46E,H46F), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C15A(H15A,
 H15B,H15C), C15B(H15D,H15E,H15F), C16A(H16A,H16B,H16C), C16B(H16D,H16E,H16F),
 C28A(H28A,H28B,H28C), C29A(H29A,H29B,H29C), C30A(H30A,H30B,H30C), C31A(H31A,
 H31B,H31C), C43A(H43A,H43B,H43C), C44A(H44A,H44B,H44C), C45A(H45A,H45B,H45C),
 C46A(H46A,H46B,H46C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'