Selective Aromatic C‒H Hydroxylation Enabled by η6-Coordination to Iridium(III)
D’Amato, Erica M.; Neumann, Constanze N.; Ritter, Tobias; Organometallics 34 (2015) 4626–; doi:10.1021/acs.organomet.5b00731

data_4086274
_publ_section_title
;
 Selective Aromatic C--H Hydroxylation Enabled by \h6-Coordination to
 Iridium(III)
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4626
_journal_paper_doi               10.1021/acs.organomet.5b00731
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C16 H20 Ir O, B F4, C2 H3 N'
_chemical_formula_sum            'C18 H23 B F4 Ir N O'
_chemical_formula_weight         548.38
_chemical_name_systematic
;
 ? 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.784(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            20
_cell_length_a                   26.4511(17)
_cell_length_b                   9.2696(7)
_cell_length_c                   39.413(3)
_cell_measurement_reflns_used    5691
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.41
_cell_volume                     9574.7(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            135625
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         1.04
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.016
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0904 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.7534.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             5280
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.054
_refine_diff_density_max         2.674
_refine_diff_density_min         -2.874
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1061
_refine_ls_number_reflns         16909
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0085P)^2^+143.7741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                12881
_reflns_number_total             16909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00731_si_002.cif
_cod_data_source_block           0604a_a
_cod_database_code               4086274
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
B1 \\sim B2 \\sim F44 \\sim F008 \\sim F46A \\sim F45A \\sim F46 \\sim F45:
within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5)
Uanis(C6) = Uanis(C7) = Uanis(C8) = Uanis(C9) = Uanis(C10)
Uanis(C11) = Uanis(C12) = Uanis(C13) = Uanis(C14) = Uanis(C15)
Uanis(C16) = Uanis(C17) = Uanis(C18) = Uanis(C19) = Uanis(C20)
Uanis(C22) = Uanis(C23) = Uanis(C24)
Uanis(C30) = Uanis(C31) = Uanis(C32) = Uanis(C34)
Uanis(C35) = Uanis(C36)
Uanis(B1) = Uanis(B2)
Uanis(F008) = Uanis(F44) = Uanis(F45) = Uanis(F46) = Uanis(F45A) = Uanis(F46A)
3. Others
 Sof(B2)=Sof(F46A)=Sof(F46)=1-FVAR(1)
 Sof(B1)=Sof(F45)=Sof(F45A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C01B(H01B), C01S(H01S), C01V(H01V), C31(H31), C028(H028), C00Q(H00Q),
 C00T(H00T), C34(H34), C013(H013), C017(H017), C01D(H01D), C01H(H01H),
 C01P(H01P), C32(H32), C022(H022), C00W(H00W), C00Y(H00Y), C30(H30), C35(H35),
 C36(H36), C01I(H01I), C01Q(H01Q), C01W(H01W), C018(H018), C33(H33)
4.b Idealised Me refined as rotating group:
 C02T(H02A,H02B,H02C), C03G(H03A,H03B,H03C), C025(H02D,H02E,H02F), C032(H03D,
 H03E,H03F), C035(H03G,H03H,H03I), C02M(H02G,H02H,H02I), C02U(H02J,H02K,H02L),
 C02X(H02M,H02N,H02O), C033(H03J,H03K,H03L), C038(H03M,H03N,H03O), C02L(H02P,
 H02Q,H02R), C02O(H02S,H02T,H02U), C02R(H02V,H02W,H02X), C03C(H03P,H03Q,H03R),
 C03F(H03S,H03T,H03U), C02P(H02Y,H,HA), C03E(H03V,H03W,H03X), C03H(H03Y,HB,HC),
 C03I(H03Z,HD,HE), C03M(H03,HF,HG), C02G(H02Z,HH,HI), C02Y(H02,HJ,HK),
 C031(H0AA,HL,HM), C034(H1AA,HN,HO), C036(H2AA,HP,HQ), C02Z(H3AA,HR,HS),
 C02W(H4AA,HT,HU), C02S(H5AA,HV,HW), C023(H6AA,HX,HY), C02V(H7AA,HZ,H8AA)
;
_olex2_submission_special_instructions 'No special instructions were received'