An electrospray-active N-heterocyclic carbene ligand for real-time analysis of organometallic reactions.
Killeen, Charles; Oliver, Allen G.; McIndoe, J. Scott; Dalton transactions (Cambridge, England : 2003) 54 (2025) 1365–1369; doi:10.1039/d4dt03243h

data_7717667
_publ_section_title
;
 An electrospray-active N-heterocyclic carbene ligand for real-time
 analysis of organometallic reactions.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1365
_journal_page_last               1369
_journal_paper_doi               10.1039/d4dt03243h
_journal_volume                  54
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C41 H45 N2 P), 4(F6 P), 1.5(H2 O)'
_chemical_formula_sum            'C82 H93 F24 N4 O1.5 P6'
_chemical_formula_weight         1800.42
_chemical_name_common            ESIMes
_chemical_name_systematic
'1,3-dimesityl-5-(2-(triphenylphosphonio)ethyl)imidazolinium dihexafluorophosphate'
_chemical_properties_physical    Moisture-sensitive,Hygroscopic
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method
;FinalCif V128 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-10-16 deposited with the CCDC.	2024-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.961(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5558(5)
_cell_length_b                   21.0574(12)
_cell_length_c                   21.9139(14)
_cell_measurement_reflns_used    9706
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      66.1365
_cell_measurement_theta_min      2.9305
_cell_volume                     4343.1(4)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2021)'
_computing_data_collection       'Bruker APEX-4 (Bruker, 2021)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2021)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material
'FinalCIF (Kratzert, 2023)/CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON-III'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       'combination of \w and \f-scans'
_diffrn_radiation_monochromator  'HELIOS Multi-layer'
_diffrn_radiation_source         'Incoatec Diamond micro-focus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            95092
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.871
_diffrn_reflns_theta_min         2.047
_diffrn_source_current           1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.018
_exptl_absorpt_correction_T_max  0.8643
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       rod
_exptl_crystal_F_000             1862
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,2-dichloroethane, hexanes'
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
'Refined as an inversion twin. Twin domain ratio: 0.61:0.39.'
_refine_ls_abs_structure_Flack   0.40(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1172
_refine_ls_number_reflns         16012
_refine_ls_number_restraints     187
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0740
_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^)+(0.1396P)^2^+1.1685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2280
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                12073
_reflns_number_total             16012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt03243h2.cif
_cod_data_source_block           ckjsm2302
_cod_depositor_comments          'Adding full bibliography for 7717667.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C82 H93 F24 N4 O1.50 P6'
_cod_database_code               7717667
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.704
_shelx_estimated_absorpt_t_max   0.899
_shelx_res_checksum              45180
_shelx_hkl_checksum              84386