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_4087867
_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         'C32 H42 Ir N6 O4, C32 H12 B F24'
_chemical_formula_sum            'C64 H54 B F24 Ir N6 O4'
_chemical_formula_weight         1630.14
_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   mixed
_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                106.251(2)
_cell_angle_beta                 108.604(2)
_cell_angle_gamma                104.9131(19)
_cell_formula_units_Z            2
_cell_length_a                   14.3830(3)
_cell_length_b                   15.0025(4)
_cell_length_c                   18.0812(5)
_cell_measurement_reflns_used    20169
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.1190
_cell_measurement_theta_min      3.0590
_cell_volume                     3282.26(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   19.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4718  -99.0000   30.0000 26

  2 omega   -5.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4718   77.0000 -150.0000 30

  3 omega   81.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4718 -178.0000  -30.0000 26

  4 omega  -51.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4718  -38.0000  -30.0000 86

  5 omega  -22.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4718  -99.0000   90.0000 87

  6 omega   68.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4718   77.0000 -150.0000 26

  7 omega  -49.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.5655   38.0000 -180.0000 84

  8 omega  -51.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.5655   38.0000  -90.0000 59

  9 omega  -30.00    5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.5655  -57.0000   90.0000 35

 10 omega   -8.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.5655   57.0000  -90.0000 52

 11 omega  -34.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.5655  -77.0000  -90.0000 43

 12 omega  -99.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.5655  -57.0000 -150.0000 38

 13 omega -103.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.5655  -77.0000   60.0000 112
;
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0549169000
_diffrn_orient_matrix_UB_12      -0.0182478000
_diffrn_orient_matrix_UB_13      -0.0266601000
_diffrn_orient_matrix_UB_21      0.0107689000
_diffrn_orient_matrix_UB_22      -0.0136151000
_diffrn_orient_matrix_UB_23      -0.0363209000
_diffrn_orient_matrix_UB_31      -0.0059496000
_diffrn_orient_matrix_UB_32      -0.0481521000
_diffrn_orient_matrix_UB_33      0.0006737000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            50594
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        27.103
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.918
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1620
_exptl_crystal_recrystallization_method
'Crystals grown from C6H4F2-heptane at 293 K'
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     999
_refine_ls_number_reflns         14458
_refine_ls_number_restraints     442
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0335P)^2^+2.3379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0666
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13270
_reflns_number_total             14458
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00658_si_003.cif
_cod_data_source_block           0068abc14
_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        3282.23(15)
_cod_database_code               4087867
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All Ir(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C208-F4 \\sim C208-F5 \\sim C208-F6 \\sim C208-F4A \\sim C208-F5A \\sim
C208-F6A
 with sigma of 0.01
 F4-F5 \\sim F5-F6 \\sim F6-F4 \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
 with sigma of 0.01
 C205-F4 \\sim C205-F5 \\sim C205-F6 \\sim C205-F4A \\sim C205-F5A \\sim
C205-F6A
 with sigma of 0.01
 C231-F19 \\sim C231-F20 \\sim C231-F21 \\sim C231-F19A \\sim C231-F20A \\sim
C231-F21A
 with sigma of 0.01
 F19-F20 \\sim F20-F21 \\sim F21-F19 \\sim F19A-F20A \\sim F20A-F21A \\sim
F21A-F19A
 with sigma of 0.01
 C227-F19 \\sim C227-F20 \\sim C227-F21 \\sim C227-F19A \\sim C227-F20A \\sim
C227-F21A
 with sigma of 0.01
 C223-F13A \\sim C223-F14A \\sim C223-F15A \\sim C223-F13 \\sim C223-F14 \\sim
C223-F15
 with sigma of 0.01
 F13A-F14A \\sim F14A-F15A \\sim F15A-F13A \\sim F13-F14 \\sim F14-F15 \\sim
F15-F13
 with sigma of 0.01
 C219-F13A \\sim C219-F14A \\sim C219-F15A \\sim C219-F13 \\sim C219-F14 \\sim
C219-F15
 with sigma of 0.01
 Ir1-H2 \\sim Ir1-H3
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F0AA \\sim F1 \\sim F1AA \\sim F4 \\sim F4A \\sim F5 \\sim F5A \\sim F6 \\sim
F6A \\sim F7 \\sim F8 \\sim F9 \\sim F10 \\sim F11 \\sim F12 \\sim F13 \\sim
F13A \\sim F14 \\sim F14A \\sim F15 \\sim F15A \\sim F16 \\sim F17 \\sim F18
\\sim F19 \\sim F19A \\sim F20 \\sim F20A \\sim F21 \\sim F21A \\sim F22 \\sim
F23 \\sim F24: within 1.7A with sigma of 0.007 and sigma for terminal atoms of
0.02
Uanis(F0AA) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1AA) \\sim Ueq, Uanis(F4)
\\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A) \\sim Ueq,
Uanis(F6) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim
Ueq, Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq,
Uanis(F12) \\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(F19A) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F20A) \\sim Ueq,
Uanis(F21) \\sim Ueq, Uanis(F21A) \\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
4. Others
 Sof(F19A)=Sof(F20A)=Sof(F21A)=1-FVAR(1)
 Sof(F19)=Sof(F20)=Sof(F21)=FVAR(1)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=1-FVAR(2)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(2)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(3)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C25(H25A,H25B), C28(H28A,H28B)
5.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C36(H36), C37(H37), C38(H38), C41(H41), C42(H42), C43(H43),
 C44(H44), 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:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C)
;
_shelx_shelxl_version_number     2014/7
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'