Synthesis and reactivity of iridium complexes of a macrocyclic PNP pincer ligand.
Hood, Thomas M.; Chaplin, Adrian B.; Dalton transactions (Cambridge, England : 2003) 50 (2021) 2472–2482; doi:10.1039/d0dt04303f

data_7706528
_publ_section_title
;
 Synthesis and reactivity of iridium complexes of a macrocyclic PNP pincer
 ligand.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2472
_journal_page_last               2482
_journal_paper_doi               10.1039/d0dt04303f
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety
'C29 H51 Ir N P2, 0.5(C6 H4 F2), C32 H12 B F24'
_chemical_formula_sum            'C64 H65 B F25 Ir N P2'
_chemical_formula_weight         1588.12
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-18 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.977(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5966(3)
_cell_length_b                   20.6443(6)
_cell_length_c                   25.5399(7)
_cell_measurement_reflns_used    22676
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.8430
_cell_measurement_theta_min      2.9360
_cell_volume                     7167.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -42.00  10.00   1.00   14.00    --  -22.18 -77.00 -90.00   52
  2  \w    -42.00  10.00   1.00   14.00    --  -22.18 -77.00 120.00   52
  3  \w   -111.00 -61.00   1.00   14.00    --  -22.18-178.00 150.00   50
  4  \w     -1.00  98.00   1.00   14.00    --   23.58  37.00 150.00   99
  5  \w    -15.00  64.00   1.00   14.00    --   23.58 -99.00  60.00   79
  6  \w    -97.00   2.00   1.00   14.00    --  -22.18 -37.00-150.00   99
  7  \w    -42.00  -4.00   1.00   14.00    --  -22.18 -77.00   0.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction: SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0069612000
_diffrn_orient_matrix_UB_12      0.0187337000
_diffrn_orient_matrix_UB_13      0.0229091000
_diffrn_orient_matrix_UB_21      0.0319433000
_diffrn_orient_matrix_UB_22      0.0241146000
_diffrn_orient_matrix_UB_23      -0.0098277000
_diffrn_orient_matrix_UB_31      -0.0406835000
_diffrn_orient_matrix_UB_32      0.0157367000
_diffrn_orient_matrix_UB_33      -0.0122419000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0434
_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       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            89109
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        29.574
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         2.933
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.010
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.318
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3172
_exptl_crystal_recrystallization_method
'Crystals grown from 1,2-F2C6H4-SiMe4 at 243 K'
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.193
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1031
_refine_ls_number_reflns         20104
_refine_ls_number_restraints     856
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0267P)^2^+9.7413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15298
_reflns_number_total             20104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt04303f2.cif
_cod_data_source_block           0579abc19s
_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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7706524--7706528.cif.
;
_cod_database_code               7706528
_shelx_shelxl_version_number     2014/7
_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
 C215-F7 \\sim C215-F8 \\sim C215-F9 \\sim C215-F7A \\sim C215-F8A \\sim
C215-F9A
 with sigma of 0.01
 F7-F8 \\sim F8-F9 \\sim F9-F7 \\sim F7A-F8A \\sim F8A-F9A \\sim F9A-F7A
 with sigma of 0.01
 C211-F7 \\sim C211-F8 \\sim C211-F9 \\sim C211-F7A \\sim C211-F8A \\sim
C211-F9A
 with sigma of 0.01
 C216-F10 \\sim C216-F11 \\sim C216-F12 \\sim C216-F10A \\sim C216-F11A \\sim
C216-F12A
 with sigma of 0.01
 F10-F11 \\sim F11-F12 \\sim F12-F10 \\sim F10A-F11A \\sim F11A-F12A \\sim
F12A-F10A
 with sigma of 0.01
 C213-F10 \\sim C213-F11 \\sim C213-F12 \\sim C213-F10A \\sim C213-F11A \\sim
C213-F12A
 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
 C232-F22 \\sim C232-F23 \\sim C232-F24 \\sim C232-F22A \\sim C232-F23A \\sim
C232-F24A
 with sigma of 0.01
 F22-F23 \\sim F23-F24 \\sim F24-F22 \\sim F22A-F23A \\sim F23A-F24A \\sim
F24A-F22A
 with sigma of 0.01
 C229-F22 \\sim C229-F23 \\sim C229-F24 \\sim C229-F22A \\sim C229-F23A \\sim
C229-F24A
 with sigma of 0.01
 C219-C223 \\sim C219-C323
 with sigma of 0.01
 F25-C401 \\sim F26A-C406 \\sim F26-C402
 with sigma of 0.01
 C406-F25 \\sim C402-F25 \\sim C401-F26 \\sim C403-F26 \\sim C405-F26A \\sim
C401-F26A
 with sigma of 0.01
 C223-F13 \\sim C223-F14 \\sim C223-F15 \\sim C323-F13A \\sim C323-F14A \\sim
C323-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
3. Restrained planarity
 F25, C401, C402, C403, C404, C405, C406, F26, F26A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
F25 \\sim F26 \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7
\\sim F7A \\sim F8 \\sim F8A \\sim F9 \\sim F9A \\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 F19A \\sim F20
\\sim F20A \\sim F21 \\sim F21A \\sim F22 \\sim F22A \\sim F23 \\sim F23A \\sim
F24 \\sim F24A \\sim F26A \\sim C401 \\sim C402 \\sim C403 \\sim C404 \\sim
C405 \\sim C406 \\sim C323 \\sim C223: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(F25) \\sim Ueq, Uanis(F26) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2)
\\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq,
Uanis(F6) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F8) \\sim
Ueq, Uanis(F8A) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F9A) \\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(F19A) \\sim Ueq, Uanis(F20)
\\sim Ueq, Uanis(F20A) \\sim Ueq, Uanis(F21) \\sim Ueq, Uanis(F21A) \\sim Ueq,
Uanis(F22) \\sim Ueq, Uanis(F22A) \\sim Ueq, Uanis(F23) \\sim Ueq, Uanis(F23A)
\\sim Ueq, Uanis(F24) \\sim Ueq, Uanis(F24A) \\sim Ueq, Uanis(F26A) \\sim Ueq,
Uanis(C401) \\sim Ueq, Uanis(C402) \\sim Ueq, Uanis(C403) \\sim Ueq,
Uanis(C404) \\sim Ueq, Uanis(C405) \\sim Ueq, Uanis(C406) \\sim Ueq,
Uanis(C323) \\sim Ueq, Uanis(C223) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C323) = Uanis(C223)
5. Others
 Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(1)
 Sof(F22)=Sof(F23)=Sof(F24)=FVAR(1)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(2)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(2)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(C323)=1-FVAR(3)
 Sof(F13)=Sof(F14)=Sof(F15)=Sof(C223)=FVAR(3)
 Fixed Sof: F25(0.5) C401(0.5) C402(0.5) H402(0.25) C403(0.5) H403(0.5)
 C404(0.5) H404(0.5) C405(0.5) H405(0.5) C406(0.5) H406(0.25) F26(0.25) F7(0.5)
 F7A(0.5) F8(0.5) F8A(0.5) F9(0.5) F9A(0.5) F19(0.5) F19A(0.5) F20(0.5)
 F20A(0.5) F21(0.5) F21A(0.5) F26A(0.25)
6.a Ternary CH refined with riding coordinates:
 C119(H119), C120(H120), C121(H121)
6.b Secondary CH2 refined with riding coordinates:
 C107(H10A,H10B), C108(H10C,H10D), C117(H11S,H11T), C118(H11U,H11V), C122(H12A,
 H12B), C123(H12C,H12D), C124(H12E,H12F), C125(H12G,H12H), C126(H12I,H12J),
 C127(H12K,H12L), C128(H12M,H12N), C129(H12O,H12P), C130(H13A,H13B)
6.c Aromatic/amide H refined with riding coordinates:
 C103(H103), C104(H104), C105(H105), C402(H402), C403(H403), C404(H404),
 C405(H405), C406(H406), C202(H202), C204(H204), C206(H206), C210(H210),
 C212(H212), C214(H214), C218(H218), C220(H220), C222(H222), C226(H226),
 C228(H228), C230(H230)
6.d Fitted hexagon refined as free rotating group:
 C401(C402,C403,C404,C405,C406)
6.e Idealised Me refined as rotating group:
 C110(H11A,H11B,H11C), C111(H11D,H11E,H11F), C112(H11G,H11H,H11I), C114(H11J,
 H11K,H11L), C115(H11M,H11N,H11O), C116(H11P,H11Q,H11R)
;
_shelx_res_checksum              51158
_shelx_hkl_checksum              86108
_shelx_fab_checksum              46403
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.777
_oxdiff_exptl_absorpt_empirical_full_min 0.618