A redox switchable ferrocene decorated n-heterocyclic carbene (NHC) palladium catalyst for cross coupling of arylboronic acid and acetic anhydride in phosphine, base and additive free conditions
Bora, Debashree; Ali, Abdul Aziz; Saha, Biswajit; New Journal of Chemistry 48 (2024) 615–620; doi:10.1039/D3NJ04997C

data_7062890
_publ_section_title
;
 A redox switchable ferrocene decorated n-heterocyclic carbene (NHC)
 palladium catalyst for cross coupling of arylboronic acid and acetic
 anhydride in phosphine, base and additive free conditions
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              615
_journal_page_last               620
_journal_paper_doi               10.1039/D3NJ04997C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C25 H26 Fe N3 O2 Pd, F6 P'
_chemical_formula_sum            'C25 H26 F6 Fe N3 O2 P Pd'
_chemical_formula_weight         707.71
_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     iterative
_audit_creation_date             2022-08-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-08-29 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                110.729(2)
_cell_angle_beta                 101.751(2)
_cell_angle_gamma                93.823(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5977(2)
_cell_length_b                   11.8495(3)
_cell_length_c                   12.2334(3)
_cell_measurement_reflns_used    15815
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      68.0500
_cell_measurement_theta_min      3.9660
_cell_volume                     1259.23(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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   -108.00 -22.00   0.50    0.20    --  -41.33 -50.00  -4.00  172
  2  \w    -56.00  25.00   0.50    0.20    --  -41.33  50.00 141.00  162
  3  \w   -149.00 -63.00   0.50    0.64    --  -82.50 -50.00  -4.00  172
  4  \w    -56.00 -16.00   0.50    0.64    --  -82.50  50.00 141.00   80
  5  \w     78.00 163.00   0.50    0.64    --   96.67  50.00 141.00  170
  6  \w     30.00  57.00   0.50    0.64    --   96.67 -50.00  -4.00   54
  7  \w    -24.00  35.00   0.50    0.20    --  -41.33  11.00 -60.00  118
  8  \w    -37.00  27.00   0.50    0.20    --  -41.33  32.00-150.00  128
  9  \w    -28.00  30.00   0.50    0.20    --  -41.33  21.00 150.00  116
 10  \w     11.00  43.00   0.50    0.20    --   41.33  88.00  21.65   64
 11  \w     22.00 108.00   0.50    0.20    --   41.33  50.00 141.00  172
 12  \w    -25.00  57.00   0.50    0.20    --   41.33 -50.00  -4.00  164
 13  \w     12.00  43.00   0.50    0.20    --   41.33  84.00-124.82   62
 14  \w    -21.00  73.00   0.50    0.20    --   41.33 -89.00-120.00  188
 15  \w    -34.00  24.00   0.50    0.20    --   41.33 -11.00  30.00  116
 16  \w    -25.00  62.00   0.50    0.20    --   41.33 -54.00 -90.00  174
 17  \w      8.00  35.00   0.50    0.20    --   41.33  94.00 -31.14   54
 18  \w     41.00 100.00   0.50    0.20    --   41.33-138.00-150.00  118
 19  \w     28.00 109.00   0.50    0.20    --   41.33  32.00   0.00  162
 20  \w     41.00 100.00   0.50    0.20    --   41.33-138.00-120.00  118
 21  \w    -47.00 -15.00   0.50    0.64    --  -82.50  42.00 -60.00   64
 22  \w   -157.00 -83.00   0.50    0.64    --  -82.50 -96.00  60.00  148
 23  \w   -101.00 -23.00   0.50    0.64    --  -82.50 145.00 150.00  156
 24  \w    -47.00 -15.00   0.50    0.64    --  -82.50  42.00 -30.00   64
 25  \w     28.00 105.00   0.50    0.64    --   96.67 -77.00   0.00  154
 26  \w     30.00 109.00   0.50    0.64    --   96.67-117.00-150.00  158
 27  \w     30.00  57.00   0.50    0.64    --   96.67 -50.00-150.00   54
 28  \w     30.00  57.00   0.50    0.64    --   96.67 -50.00   0.00   54
 29  \w     22.00 106.00   0.50    0.64    --   96.67 -96.00 -30.00  168
 30  \w     22.00 106.00   0.50    0.64    --   96.67 -96.00  60.00  168
 31  \w     29.00  83.00   0.50    0.64    --   96.67 -68.00  60.00  108
 32  \w     44.00 127.00   0.50    0.64    --   96.67-145.00  30.00  166
 33  \w     82.00 167.00   0.50    0.64    --   96.67  25.00-150.00  170
 34  \w     30.00  57.00   0.50    0.64    --   96.67 -50.00 -90.00   54
 35  \w     29.00  83.00   0.50    0.64    --   96.67 -68.00-180.00  108
 36  \w     83.00 164.00   0.50    0.64    --   96.67  33.00 120.00  162
 37  \w     28.00 105.00   0.50    0.64    --   96.67 -77.00 -90.00  154
 38  \w     44.00 127.00   0.50    0.64    --   96.67-145.00 120.00  166
 39  \w     30.00 109.00   0.50    0.64    --   96.67-117.00 -90.00  158
 40  \w     29.00  68.00   0.50    0.64    --   96.67 -59.00 -60.00   78
 41  \w     44.00 127.00   0.50    0.64    --   96.67-145.00-120.00  166
 42  \w     29.00  68.00   0.50    0.64    --   96.67 -59.00  90.00   78
 43  \w     83.00 164.00   0.50    0.64    --   96.67  33.00-120.00  162
 44  \w     73.00 165.00   0.50    0.64    --   96.67  68.00  60.00  184
 45  \w     30.00 109.00   0.50    0.64    --   96.67-117.00  30.00  158
 46  \w     78.00 163.00   0.50    0.64    --   96.67  50.00-120.00  170
 47  \w     83.00 164.00   0.50    0.64    --   96.67  33.00  90.00  162
 48  \w     27.00 127.00   0.50    0.64    --   96.67 -87.00 120.00  200
 49  \w     70.00 165.00   0.50    0.64    --   96.67  77.00 150.00  190
 50  \w     30.00 109.00   0.50    0.64    --   96.67-117.00 -60.00  158
 51  \w    -61.00  26.00   0.50    0.20    --  -41.33  54.00  30.00  174
 52  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00  30.00  182
 53  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00  90.00  192
 54  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00 -60.00  192
 55  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00  60.00  182
 56  \w   -108.00 -21.00   0.50    0.20    --  -41.33 -54.00 120.00  174
 57  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00-150.00  192
 58  \w   -109.00 -18.00   0.50    0.20    --  -41.33 -65.00 -30.00  182
 59  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00 -90.00  192
 60  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00  30.00  192
 61  \w   -110.00 -14.00   0.50    0.20    --  -41.33 -77.00 120.00  192
 62  \w     15.00 110.00   0.50    0.20    --   41.33  77.00-150.00  190
 63  \w     13.00  43.00   0.50    0.20    --   41.33  82.00  76.28   60
 64  \w    -26.00  37.00   0.50    0.20    --   41.33 -32.00 -60.00  126
 65  \w     25.00 109.00   0.50    0.20    --   41.33  43.00 -60.00  168
 66  \w     18.00 109.00   0.50    0.20    --   41.33  65.00-150.00  182
 67  \w     10.00  43.00   0.50    0.20    --   41.33  89.00 -61.93   66
 68  \w     12.00  43.00   0.50    0.20    --   41.33  84.00 143.45   62
 69  \w     71.00 165.00   0.50    0.64    --   96.67  73.00 -76.77  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21859
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.206
_diffrn_reflns_theta_min         3.984
_exptl_absorpt_coefficient_mu    11.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         4578
_refine_ls_number_restraints     465
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+1.0476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4342
_reflns_number_total             4578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj04997c2.cif
_cod_data_source_block           sdb_116_sudip1
_cod_depositor_comments          'Adding full bibliography for 7062890.cif.'
_cod_original_cell_volume        1259.23(5)
_cod_database_code               7062890
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.496
_shelx_estimated_absorpt_t_min   0.242
_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
 F1-P1 \\sim F1A-P1
 with sigma of 0.02
 F2-P1 \\sim F2A-P1
 with sigma of 0.02
 F4-P1 \\sim F4A-P1
 with sigma of 0.02
 F6-P1 \\sim F6A-P1
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F4A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F4)=Sof(F6)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22)
6.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              89757
_shelx_hkl_checksum              6534
_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
;