P(V)-bis(amidophenolate) ligand cooperation: stoichiometric CO-bond cleavage in aldehydes and ketones.
Karnbrock, Simon B. H.; Golz, Christopher; Alcarazo, Manuel; Chemical communications (Cambridge, England) 60 (2024) 6745–6748; doi:10.1039/d4cc02202e

data_7133146
_publ_section_title
;
 P(V)-bis(amidophenolate) ligand cooperation: stoichiometric
 C&#xe001;O-bond cleavage in aldehydes and ketones.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6745
_journal_page_last               6748
_journal_paper_doi               10.1039/d4cc02202e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C45 H60 N2 O3 P, C32 H12 B F24, 2(C7 H8)'
_chemical_formula_sum            'C91 H88 B F24 N2 O3 P'
_chemical_formula_weight         1755.41
_chemical_name_systematic
'5-[(adamantan-1-yl)methylidene]-7,9,13,15-tetra-t-butyl-11-oxo-5H,11H-11\l5-dibenzo[4,5:7,8][1,3,6,2]oxadiazaphosphocino[2,3-b][1,3,2]benzoxazaphosphol-5-ium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate toluene solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-28
_audit_creation_method
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-05-28 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.898(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9705(8)
_cell_length_b                   31.6393(19)
_cell_length_c                   19.2626(12)
_cell_measurement_reflns_used    9648
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.475
_cell_measurement_theta_min      2.169
_cell_volume                     8494.7(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS 8.5.1.2 Release/2023-09-07 and APEX5 2023.9-2'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Ag'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            200748
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         1.947
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9302
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1311 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.9302.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             3632
_exptl_crystal_recrystallization_method 'Crystallized from warm toluene.'
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.277
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1354
_refine_ls_number_reflns         19461
_refine_ls_number_restraints     446
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0252P)^2^+11.7819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15821
_reflns_number_total             19461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02202e2.cif
_cod_data_source_block           mo_2330_cg_0m
_cod_depositor_comments
'Adding full bibliography for 7133142--7133149.cif.'
_cod_database_code               7133146
_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
 C78A-C79A
 1.51 with sigma of 0.02
 C79A-C80A = C79A-C84A = C81A-C82A
 1.39 with sigma of 0.02
 C80A-C81A = C82A-C83A = C83A-C84A
 1.38 with sigma of 0.02
 C78B-C79B
 1.51 with sigma of 0.02
 C79B-C84B = C79B-C80B = C83B-C82B
 1.39 with sigma of 0.02
 C84B-C83B = C82B-C81B = C81B-C80B
 1.38 with sigma of 0.02
 C85A-C86A
 1.51 with sigma of 0.02
 C86A-C91A = C86A-C87A = C90A-C89A
 1.39 with sigma of 0.02
 C91A-C90A = C89A-C88A = C88A-C87A
 1.38 with sigma of 0.02
 C85B-C86B
 1.51 with sigma of 0.02
 C86B-C91B = C86B-C87B = C90B-C89B
 1.39 with sigma of 0.02
 C91B-C90B = C89B-C88B = C88B-C87B
 1.38 with sigma of 0.02
 C78A-C80A = C78A-C84A
 2.52 with sigma of 0.04
 C79A-C81A
 2.42 with sigma of 0.04
 C79A-C83A
 2.41 with sigma of 0.04
 C80A-C82A
 2.39 with sigma of 0.04
 C81A-C83A = C82A-C84A
 2.4 with sigma of 0.04
 C78B-C84B = C78B-C80B
 2.52 with sigma of 0.04
 C79B-C83B
 2.42 with sigma of 0.04
 C79B-C81B
 2.41 with sigma of 0.04
 C84B-C82B
 2.39 with sigma of 0.04
 C83B-C81B = C82B-C80B
 2.4 with sigma of 0.04
 C85A-C91A = C85A-C87A
 2.52 with sigma of 0.04
 C86A-C90A
 2.42 with sigma of 0.04
 C86A-C88A
 2.41 with sigma of 0.04
 C91A-C89A
 2.39 with sigma of 0.04
 C90A-C88A = C89A-C87A
 2.4 with sigma of 0.04
 C85B-C91B = C85B-C87B
 2.52 with sigma of 0.04
 C86B-C90B
 2.42 with sigma of 0.04
 C86B-C88B
 2.41 with sigma of 0.04
 C91B-C89B
 2.39 with sigma of 0.04
 C90B-C88B = C89B-C87B
 2.4 with sigma of 0.04
 F1A-C52A \\sim F1B-C52B
 with sigma of 0.02
 F3A-F1A \\sim F3B-F1B
 with sigma of 0.04
 F1A-F2A \\sim F1B-F2B
 with sigma of 0.04
 F1A-C48 \\sim F1B-C48
 with sigma of 0.04
 F14A-C68A \\sim F14B-C68B
 with sigma of 0.02
 F15A-C68A \\sim F15B-C68B
 with sigma of 0.02
 F13A-C68A \\sim F13B-C68B
 with sigma of 0.02
 C64-C68A \\sim C64-C68B
 with sigma of 0.02
 F14A-F15A \\sim F14B-F15B
 with sigma of 0.04
 F14A-F13A \\sim F14B-F13B
 with sigma of 0.04
 F14A-C64 \\sim F14B-C64
 with sigma of 0.04
 F15A-F13A \\sim F15B-F13B
 with sigma of 0.04
 F15A-C64 \\sim F15B-C64
 with sigma of 0.04
 F13A-C64 \\sim F13B-C64
 with sigma of 0.04
 F12A-C61A \\sim F12B-C61B
 with sigma of 0.02
 F11A-C61A \\sim F11B-C61B
 with sigma of 0.02
 F10A-C61A \\sim F10B-C61B
 with sigma of 0.02
 C58-C61A \\sim C58-C61B
 with sigma of 0.02
 F12A-F11A \\sim F12B-F11B
 with sigma of 0.04
 F12A-F10A \\sim F12B-F10B
 with sigma of 0.04
 F12A-C58 \\sim F12B-C58
 with sigma of 0.04
 F11A-F10A \\sim F11B-F10B
 with sigma of 0.04
 F11A-C58 \\sim F11B-C58
 with sigma of 0.04
 F10A-C58 \\sim F10B-C58
 with sigma of 0.04
 F3A-C52A \\sim F3B-C52B
 with sigma of 0.02
 F2A-C52A \\sim F2B-C52B
 with sigma of 0.02
 C48-C52A \\sim C48-C52B
 with sigma of 0.02
 F3A-F2A \\sim F3B-F2B
 with sigma of 0.04
 F3A-C48 \\sim F3B-C48
 with sigma of 0.04
 F2A-C48 \\sim F2B-C48
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F1B, F2B, F3B, C48, C52B
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.001
 C78A, C79A, C80A, C81A, C82A, C83A, C84A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C78B, C79B, C80B, C81B, C82B, C83B, C84B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C85B, C86B, C87B, C88B, C89B, C90B, C91B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C85A, C86A, C87A, C88A, C89A, C90A, C91A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F13A, F14A, F15A, C64, C68A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F13B, F14B, F15B, C64, C68B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F10A, F11A, F12A, C58, C61A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F10B, F11B, F12B, C58, C61B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1A, F2A, F3A, C48, C52A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(C78B)=Sof(H78D)=Sof(H78E)=Sof(H78F)=Sof(C79B)=Sof(C80B)=Sof(H80B)=
 Sof(C81B)=Sof(H81B)=Sof(C82B)=Sof(H82B)=Sof(C83B)=Sof(H83B)=Sof(C84B)=
 Sof(H84B)=1-FVAR(1)
 Sof(C78A)=Sof(H78A)=Sof(H78B)=Sof(H78C)=Sof(C79A)=Sof(C80A)=Sof(H80A)=
 Sof(C81A)=Sof(H81A)=Sof(C82A)=Sof(H82A)=Sof(C83A)=Sof(H83A)=Sof(C84A)=
 Sof(H84A)=FVAR(1)
 Sof(C85B)=Sof(H85D)=Sof(H85E)=Sof(H85F)=Sof(C86B)=Sof(C87B)=Sof(H87B)=
 Sof(C88B)=Sof(H88B)=Sof(C89B)=Sof(H89B)=Sof(C90B)=Sof(H90B)=Sof(C91B)=
 Sof(H91B)=1-FVAR(2)
 Sof(C85A)=Sof(H85A)=Sof(H85B)=Sof(H85C)=Sof(C86A)=Sof(C87A)=Sof(H87A)=
 Sof(C88A)=Sof(H88A)=Sof(C89A)=Sof(H89A)=Sof(C90A)=Sof(H90A)=Sof(C91A)=
 Sof(H91A)=FVAR(2)
 Sof(F13B)=Sof(F14B)=Sof(F15B)=Sof(C68B)=1-FVAR(3)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(C68A)=FVAR(3)
 Sof(F10B)=Sof(F11B)=Sof(F12B)=Sof(C61B)=1-FVAR(4)
 Sof(F10A)=Sof(F11A)=Sof(F12A)=Sof(C61A)=FVAR(4)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(C52B)=1-FVAR(5)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C52A)=FVAR(5)
5.a Ternary CH refined with riding coordinates:
 C38(H38), C40(H40), C43(H43)
5.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C39(H39A,H39B), C41(H41A,H41B), C42(H42A,H42B), C44(H44A,
 H44B), C45(H45A,H45B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C17(H17), C19(H19), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C47(H47), C49(H49), C51(H51), C55(H55), C57(H57), C59(H59), C63(H63),
  C65(H65), C67(H67), C71(H71), C73(H73), C75(H75), C80A(H80A), C80B(H80B),
 C81A(H81A), C81B(H81B), C82A(H82A), C82B(H82B), C83A(H83A), C83B(H83B),
 C84A(H84A), C84B(H84B), C87A(H87A), C88A(H88A), C89A(H89A), C90A(H90A),
 C91A(H91A), C87B(H87B), C88B(H88B), C89B(H89B), C90B(H90B), C91B(H91B)
5.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,
 H28B,H28C), C78A(H78A,H78B,H78C), C78B(H78D,H78E,H78F), C85A(H85A,H85B,H85C),
 C85B(H85D,H85E,H85F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.996
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              14170
_shelx_hkl_checksum              86988