Native carboxylate-assisted palladium/norbornene-mediated distal C-H functionalization of ferrocene.
Gupta, Princi; Patel, Brijesh; Waske, Shivam; Madhavan, Suchithra; Kapur, Manmohan; Chemical communications (Cambridge, England) 62 (2026) 6364–6367; doi:10.1039/d6cc00066e

data_7135467
_publ_section_title
;
 Native carboxylate-assisted palladium/norbornene-mediated distal C-H
 functionalization of ferrocene.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6364
_journal_page_last               6367
_journal_paper_doi               10.1039/d6cc00066e
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C18 H15 Fe N O4'
_chemical_formula_sum            'C18 H15 Fe N O4'
_chemical_formula_weight         365.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-02-06 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6243(2)
_cell_length_b                   10.6505(3)
_cell_length_c                   19.4172(5)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    140.0
_cell_measurement_theta_max      70.12
_cell_measurement_theta_min      4.15
_cell_volume                     1576.73(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D-8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29384
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        65.098
_diffrn_reflns_theta_max         65.098
_diffrn_reflns_theta_min         4.554
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.869
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4360
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0984 after correction.
The Ratio of minimum to maximum transmission is 0.5788.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.034(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+0.7621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2553
_reflns_number_total             2639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00066e2.cif
_cod_data_source_block           fff
_cod_depositor_comments          'Adding full bibliography for 7135467.cif.'
_cod_database_code               7135467
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.966(7)
 0.034(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C9(H9), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              83948
_shelx_hkl_checksum              88915
_olex2_submission_special_instructions 'No special instructions were received'