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_7135375
_publ_section_title
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 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         'C15 H32 P, C44 H7 B2 F30 O2, 3[CH2Cl2]'
_chemical_formula_sum            'C62 H45 B2 Cl6 F30 O2 P'
_chemical_formula_weight         1657.336
_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'
_symmetry_Int_Tables_number      15
_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                 105.967(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.508(8)
_cell_length_b                   16.827(4)
_cell_length_c                   23.878(5)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    149.98
_cell_measurement_theta_max      18.48
_cell_measurement_theta_min      2.36
_cell_volume                     13717(5)
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      149.98
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3944
_diffrn_reflns_av_unetI/netI     0.3888
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9982
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            219948
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9982
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.36
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1096 before and 0.0737 after correction.
The Ratio of minimum to maximum transmission is 0.8052.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       block
_exptl_crystal_F_000             6654.237
_refine_diff_density_max         1.0433
_refine_diff_density_min         -0.8065
_refine_diff_density_rms         0.1558
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             8.6440
_refine_ls_extinction_coef       0.00096(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.8418
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    57
_refine_ls_number_parameters     857
_refine_ls_number_reflns         12058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8418
_refine_ls_R_factor_all          0.1975
_refine_ls_R_factor_gt           0.0826
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1442P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2163
_refine_ls_wR_factor_ref         0.2615
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              40
_reflns_limit_h_min              -42
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                4046
_reflns_number_total             12058
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d6cc00412a2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7135371--7135375.cif.'
_cod_original_formula_sum        'C62 H45 B2 Cl6 F30 O2 P1'
_cod_database_code               7135375
_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 Secondary CH2 refined with riding coordinates:
 C47(H47a,H47b), C78(H78a,H78b)
2.b Aromatic/amide H refined with riding coordinates:
 C50(H50), C53(H53), C63(H63), C71(H71), C83(H83), C85(H85)
2.c X=CH2 refined with riding coordinates:
 C87(H87a,H87b)
2.d Idealised Me refined as rotating group:
 C62(H62a,H62b,H62c), C72(H72a,H72b,H72c), C84(H84a,H84b,H84c), C86(H86a,H86b,
 H86c), C88(H88a,H88b,H88c), C90(H90a,H90b,H90c), C91(H91a,H91b,H91c), C92(H92a,
 H92b,H92c), C96(H96a,H96b,H96c)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 978 electrons were 
found in a volume of 3142\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
3[CH2Cl2] per Asymmetric Unit 
which account for 1008 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'