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_7133143
_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         '2(C39 H52 N2 O3 P), 2(C32 H12 B F24), C7 H8'
_chemical_formula_sum            'C149 H136 B2 F48 N4 O6 P2'
_chemical_formula_weight         3074.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-16
_audit_creation_method
;FinalCif V113 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-05-06 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                115.857(3)
_cell_angle_beta                 102.316(2)
_cell_angle_gamma                98.273(2)
_cell_formula_units_Z            1
_cell_length_a                   13.6399(13)
_cell_length_b                   16.8477(13)
_cell_length_c                   19.2953(16)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      31.559
_cell_measurement_theta_min      2.171
_cell_volume                     3754.1(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2022.1-1'
_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    'XT  (Sheldrick, 2015)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            150191
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.591
_diffrn_reflns_theta_min         2.074
_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    0.143
_exptl_absorpt_correction_T_max  0.8135
_exptl_absorpt_correction_T_min  0.7879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1324 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9685.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             1578
_exptl_crystal_recrystallization_method 'Crystallized from toluene.'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1285
_refine_ls_number_reflns         25097
_refine_ls_number_restraints     464
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0531
_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^)+(0.0631P)^2^+2.5423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19942
_reflns_number_total             25097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02202e2.cif
_cod_data_source_block           mo_1870_sk_0m
_cod_depositor_comments
'Adding full bibliography for 7133142--7133149.cif.'
_cod_database_code               7133143
_shelx_shelxl_version_number     2018/3
_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
 C72-C73
 1.51 with sigma of 0.02
 C73-C74 = C73-C78 = C75-C76
 1.39 with sigma of 0.02
 C74-C75 = C76-C77 = C77-C78
 1.38 with sigma of 0.02
 C73-C75
 2.42 with sigma of 0.04
 C74-C76
 2.39 with sigma of 0.04
 C73-C77
 2.41 with sigma of 0.04
 C75-C77 = C76-C78
 2.4 with sigma of 0.04
 C72-C74 = C72-C78
 2.52 with sigma of 0.04
 F13A-F15A \\sim F13B-F15B
 with sigma of 0.04
 F15A-C62A \\sim F15B-C62B
 with sigma of 0.02
 F7A-C54 \\sim F7B-C54
 with sigma of 0.02
 C60-F15A \\sim C60-F15B
 with sigma of 0.04
 F14A-F15A \\sim F14B-F15B
 with sigma of 0.04
 F9A-C54 \\sim F9B-C54
 with sigma of 0.02
 F8A-C54 \\sim F8B-C54
 with sigma of 0.02
 F8C-C54 \\sim F8A-C54
 with sigma of 0.02
 F7C-C54 \\sim F7A-C54
 with sigma of 0.02
 F9C-C54 \\sim F9A-C54
 with sigma of 0.02
 F7A-F8A \\sim F7B-F8B
 with sigma of 0.02
 F8A-F9A \\sim F8B-F9B
 with sigma of 0.02
 F9A-F7A \\sim F9B-F7B
 with sigma of 0.02
 F7A-F8A \\sim F7C-F8C
 with sigma of 0.02
 F8A-F9A \\sim F8C-F9C
 with sigma of 0.02
 F9A-F7A \\sim F9C-F7C
 with sigma of 0.02
 F7C-F8C \\sim F7B-F8B
 with sigma of 0.02
 F8C-F9C \\sim F8B-F9B
 with sigma of 0.02
 F9C-F7C \\sim F9B-F7B
 with sigma of 0.02
 C73-C74 \\sim C74-C75 \\sim C75-C76 \\sim C76-C77 \\sim C77-C78 \\sim C78-C73
 with sigma of 0.02
 C73-C77 \\sim C73-C75 \\sim C78-C76 \\sim C74-C78 \\sim C75-C77 \\sim C74-C76
 with sigma of 0.04
 C72-C78 \\sim C72-C74
 with sigma of 0.04
 C63-F17A \\sim C63-F17B
 with sigma of 0.02
 F16A-C63 \\sim F16B-C63
 with sigma of 0.02
 F18A-C63 \\sim F18B-C63
 with sigma of 0.02
 F13A-C62A \\sim F13B-C62B
 with sigma of 0.02
 C60-C62A \\sim C60-C62B
 with sigma of 0.02
 F13A-C60 \\sim F13B-C60
 with sigma of 0.04
 F14A-C62A \\sim F14B-C62B
 with sigma of 0.02
 F14A-F13A \\sim F14B-F13B
 with sigma of 0.04
 F14A-C60 \\sim F14B-C60
 with sigma of 0.04
 F2A-C46 \\sim F1B-C46
 with sigma of 0.02
 F3A-C46 \\sim F2B-C46
 with sigma of 0.02
 F1A-C46 \\sim F3B-C46
 with sigma of 0.02
 F11A-F12 \\sim F11B-F12
 with sigma of 0.04
 F11A-C50 \\sim F11B-C50
 with sigma of 0.04
 F10A-F12 \\sim F10B-F12
 with sigma of 0.04
 F11A-C55A \\sim F11B-C55B
 with sigma of 0.02
 F10A-C55A \\sim F10B-C55B
 with sigma of 0.02
 F10A-F11A \\sim F10B-F11B
 with sigma of 0.04
 F10A-C50 \\sim F10B-C50
 with sigma of 0.04
 F12-C55A \\sim F12-C55B
 with sigma of 0.02
 C50-C55A \\sim C50-C55B
 with sigma of 0.02
 F21A-C68 \\sim F21B-C68
 with sigma of 0.04
 F19-F21A \\sim F19-F21B
 with sigma of 0.04
 F20A-C68 \\sim F20B-C68
 with sigma of 0.04
 F20A-C70A \\sim F20B-C70B
 with sigma of 0.02
 F19-F20A \\sim F19-F20B
 with sigma of 0.04
 F21A-C70A \\sim F21B-C70B
 with sigma of 0.02
 F20A-F21A \\sim F20B-F21B
 with sigma of 0.04
 F19-C70A \\sim F19-C70B
 with sigma of 0.02
 C68-C70A \\sim C68-C70B
 with sigma of 0.02
3. Restrained planarity
 C72, C73, C74, C75, C76, C77, C78
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C72 \\sim C73 \\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C78: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C55A \\sim C55B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C70A \\sim C70B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
5. Rigid body (RIGU) restrains
 F10A, F11A, F12, C55A
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 F7A, F8A, F9A, C54
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 F7C, F8C, F9C, C54
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 F7B, F8B, F9B, C54
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 C72, C73, C74, C75, C76, C77, C78
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4B, F5B, F6B, C47
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F4C, F5C, F6C, C47
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F4A, F5A, F6A, C47
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1B, F2B, F3B, C46
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1A, F2A, F3A, C46
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1C, F2C, F3C, C46
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F16A, F17A, F18A, C63
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 F16B, F17B, F18B, C63
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 F13B, F14B, F15B, C62B
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.001
 F10B, F11B, C55B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F10A, F11A, C55A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F20B, F21B, C70B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F20A, F21A, C70A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(F4A)+Sof(F5A)+Sof(F6A)]+1*[Sof(F4C)+Sof(F5C)+Sof(F6C)]+1*[Sof(F4B)+
 Sof(F5B)+Sof(F6B)]=1 with esd of 0.00001
 1*[Sof(F7A)+Sof(F8A)+Sof(F9A)]+1*[Sof(F7C)+Sof(F8C)+Sof(F9C)]+1*[Sof(F7B)+
 Sof(F8B)+Sof(F9B)]=1 with esd of 0.00001
 1*[Sof(F1A)+Sof(F2A)+Sof(F3A)]+1*[Sof(F1B)+Sof(F2B)+Sof(F3B)]+1*[Sof(F1C)+
 Sof(F2C)+Sof(F3C)]=1 with esd of 0.00001
 Sof(F16B)=Sof(F17B)=Sof(F18B)=1-FVAR(1)
 Sof(F16A)=Sof(F17A)=Sof(F18A)=FVAR(1)
 Sof(F13B)=Sof(F14B)=Sof(F15B)=Sof(C62B)=1-FVAR(2)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(C62A)=FVAR(2)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(3)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(4)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(5)
 Sof(F4C)=Sof(F5C)=Sof(F6C)=FVAR(6)
 Sof(F4B)=Sof(F5B)=Sof(F6B)=FVAR(7)
 Sof(F7C)=Sof(F8C)=Sof(F9C)=FVAR(8)
 Sof(F7B)=Sof(F8B)=Sof(F9B)=FVAR(9)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(10)
 Sof(F1C)=Sof(F2C)=Sof(F3C)=FVAR(11)
 Fixed Sof: F10A(0.5) F10B(0.5) F11A(0.5) F11B(0.5) F20A(0.5) F20B(0.5)
 F21A(0.5) F21B(0.5) C55A(0.5) C55B(0.5) C70A(0.5) C70B(0.5) C72(0.5) H72A(0.5)
 H72B(0.5) H72C(0.5) C73(0.5) C74(0.5) H74(0.5) C75(0.5) H75(0.5) C76(0.5)
 H76(0.5) C77(0.5) H77(0.5) C78(0.5) H78(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C21(H21), C22(H22), C23(H23), C24(H24), C29(H29), C31(H31),
 C41(H41), C43(H43), C45(H45), C49(H49), C51(H51), C53(H53), C57(H57), C59(H59),
  C61(H61), C65(H65), C67(H67), C69(H69), C74(H74), C75(H75), C76(H76),
 C77(H77), C78(H78)
7.c 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), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C), C72(H72A,H72B,H72C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.988
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              51151
_shelx_hkl_checksum              92023