Beyond FLP additions: FLP deprotonation and C-O bond cleavage of aliphatic, aryl and ester derived olefins
Goraya, Armaan; Ajithkumar, V. S.; Ruhlandt, Karin; Stephan, Douglas W.; McCahill, Jenny SJ; Bedi, Vaibhav; Chemical Communications  (2026) –; doi:10.1039/D6CC00412A

data_7135373
_publ_section_title
;
 Beyond FLP additions: FLP deprotonation and C-O bond cleavage of
 aliphatic, aryl and ester derived olefins.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5531
_journal_page_last               5535
_journal_paper_doi               10.1039/d6cc00412a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C40 H47 B F15 P, 1[C6H14]'
_chemical_formula_sum            'C46 H61 B F15 P'
_chemical_formula_weight         940.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2026-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-11 deposited with the CCDC.	2026-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.385(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.918(3)
_cell_length_b                   11.1232(9)
_cell_length_c                   25.038(2)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      26.850
_cell_measurement_theta_min      2.595
_cell_volume                     8743.6(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            87992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.969
_diffrn_reflns_theta_min         1.942
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0558 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.8569.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             3936
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         10473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0758P)^2^+8.2529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8207
_reflns_number_total             10473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00412a2.cif
_cod_data_source_block           29082025_0m_a
_cod_depositor_comments
'Adding full bibliography for 7135371--7135375.cif.'
_cod_original_cell_volume        8743.6(12)
_cod_database_code               7135373
_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.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,
 H18B), C20(H20A,H20B), C19(H19A,H19B), C21(H21A,H21B)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C10(H10A,H10B,H10C),
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C8(H8A,H8B,H8C), C6(H6A,H6B,H6C),
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 428 electrons were 
found in a volume of 1360\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[C6H14] per Asymmetric Unit 
which account for 400 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              5147
_shelx_fab_checksum              96106
_olex2_submission_special_instructions 'No special instructions were received'