Reactivity of <i>N</i>-(isocyanoimino)triphenylphosphorane toward group 13 Lewis acids.
Tang, Beili; Ju, Shaoying; Yan, Weili; Chen, Ting; Stephan, Douglas W.; Wu, Yile; Chemical communications (Cambridge, England) 60 (2024) 12932–12935; doi:10.1039/d4cc04490h

data_7133800
_publ_section_title
;
 Reactivity of <i>N</i>-(isocyanoimino)triphenylphosphorane toward group
 13 Lewis acids.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12932
_journal_page_last               12935
_journal_paper_doi               10.1039/d4cc04490h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety
'C50 H30 Al F10 N4 P2, Al C12 Cl2 F10, 1.9(C7 H8), C6 H5 F'
_chemical_formula_sum            'C81.3 H50.2 Al2 Cl2 F21 N4 P2'
_chemical_formula_weight         1668.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-26 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.490(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3044(6)
_cell_length_b                   25.9421(11)
_cell_length_c                   19.9557(8)
_cell_measurement_reflns_used    9693
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      68.313
_cell_measurement_theta_min      2.902
_cell_volume                     7469.0(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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            318927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.588
_diffrn_reflns_theta_min         2.901
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.312
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0922 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.8942.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             3380
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1150
_refine_ls_number_reflns         13718
_refine_ls_number_restraints     270
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0574P)^2^+5.5229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12022
_reflns_number_total             13718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04490h2.cif
_cod_data_source_block           5f
_cod_depositor_comments
'Adding full bibliography for 7133795--7133800.cif.'
_cod_original_formula_sum        'C81.30 H50.20 Al2 Cl2 F21 N4 P2'
_cod_database_code               7133800
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.753
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F22-C02W \\sim F23-C75
 with sigma of 0.02
 C02W-C02T \\sim C75-C74
 with sigma of 0.02
 C02W-C02Y \\sim C75-C72
 with sigma of 0.02
 C02T-C02U \\sim C74-C02V
 with sigma of 0.02
 C02U-C02R \\sim C02V-C51
 with sigma of 0.02
 C02R-C02X \\sim C51-C73
 with sigma of 0.02
 C02X-C02Y \\sim C73-C72
 with sigma of 0.02
 F22-C02T \\sim F23-C74
 with sigma of 0.04
 F22-C02Y \\sim F23-C72
 with sigma of 0.04
 C02W-C02U \\sim C75-C02V
 with sigma of 0.04
 C02W-C02X \\sim C75-C73
 with sigma of 0.04
 C02T-C02R \\sim C74-C51
 with sigma of 0.04
 C02T-C02Y \\sim C74-C72
 with sigma of 0.04
 C02U-C02X \\sim C02V-C73
 with sigma of 0.04
 C02R-C02Y \\sim C51-C72
 with sigma of 0.04
 F23-C75 \\sim F21-C5A
 with sigma of 0.02
 C75-C74 \\sim C5A-C4A
 with sigma of 0.02
 C75-C72 \\sim C5A-C1A
 with sigma of 0.02
 C74-C02V \\sim C4A-C76
 with sigma of 0.02
 C02V-C51 \\sim C76-C3A
 with sigma of 0.02
 C51-C73 \\sim C3A-C2A
 with sigma of 0.02
 C73-C72 \\sim C2A-C1A
 with sigma of 0.02
 F23-C74 \\sim F21-C4A
 with sigma of 0.04
 F23-C72 \\sim F21-C1A
 with sigma of 0.04
 C75-C02V \\sim C5A-C76
 with sigma of 0.04
 C75-C73 \\sim C5A-C2A
 with sigma of 0.04
 C74-C51 \\sim C4A-C3A
 with sigma of 0.04
 C74-C72 \\sim C4A-C1A
 with sigma of 0.04
 C02V-C73 \\sim C76-C2A
 with sigma of 0.04
 C51-C72 \\sim C3A-C1A
 with sigma of 0.04
 C032-C033 \\sim C81-C77
 with sigma of 0.02
 C032-C02Z \\sim C81-C78
 with sigma of 0.02
 C033-C035 \\sim C77-C79
 with sigma of 0.02
 C035-C031 \\sim C79-C80
 with sigma of 0.02
 C031-C030 \\sim C80-C40
 with sigma of 0.02
 C030-C02Z \\sim C40-C78
 with sigma of 0.02
 C02Z-C034 \\sim C78-C0
 with sigma of 0.02
 C032-C035 \\sim C81-C79
 with sigma of 0.04
 C032-C030 \\sim C81-C40
 with sigma of 0.04
 C032-C034 \\sim C81-C0
 with sigma of 0.04
 C033-C031 \\sim C77-C80
 with sigma of 0.04
 C033-C02Z \\sim C77-C78
 with sigma of 0.04
 C035-C030 \\sim C79-C40
 with sigma of 0.04
 C031-C02Z \\sim C80-C78
 with sigma of 0.04
 C030-C034 \\sim C40-C0
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
F23 \\sim C75 \\sim C74 \\sim C72 \\sim C02V \\sim C73 \\sim C51: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F21 \\sim C5A \\sim C4A \\sim C1A \\sim C76 \\sim C2A \\sim C3A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F22 \\sim C02W \\sim C02T \\sim C02Y \\sim C02U \\sim C02X \\sim C02R: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C80) \\sim Ueq, Uanis(C0) \\sim Ueq, Uanis(C78) \\sim Ueq, Uanis(C40)
\\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C79) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C034) \\sim Ueq, Uanis(C032) \\sim Ueq, Uanis(C033) \\sim Ueq,
Uanis(C02Z) \\sim Ueq, Uanis(C035) \\sim Ueq, Uanis(C030) \\sim Ueq,
Uanis(C031) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: F22(0.5) C02W(0.5) C02T(0.5) H02T(0.5) C02U(0.5) H02U(0.5)
 C02R(0.5) H02R(0.5) C02X(0.5) H02X(0.5) C02Y(0.5) H02Y(0.5) C032(0.6)
 H032(0.6) C033(0.6) H033(0.6) C035(0.6) H035(0.6) C031(0.6) H031(0.6)
 C030(0.6) H030(0.6) C02Z(0.6) C034(0.6) H03A(0.6) H03B(0.6) H03C(0.6) F23(0.3)
 C75(0.3) C74(0.3) H74(0.3) C02V(0.3) H02V(0.3) C51(0.3) H51(0.3) C73(0.3)
 H73(0.3) C72(0.3) H72(0.3) F21(0.2) C5A(0.2) C4A(0.2) H4A(0.2) C76(0.2)
 H76(0.2) C3A(0.2) H3A(0.2) C2A(0.2) H2A(0.2) C1A(0.2) H1A(0.2) C0(0.3)
 H0A(0.3) H0B(0.3) H0C(0.3) C80(0.3) H80(0.3) C79(0.3) H79(0.3) C77(0.3)
 H77(0.3) C81(0.3) H81(0.3) C78(0.3) C40(0.3) H40(0.3)
5.a Aromatic/amide H refined with riding coordinates:
 C41(H41), C26(H26), C45(H45), C31(H31), C27(H27), C34(H34), C14(H14),
 C10(H10), C47(H47), C44(H44), C22(H22), C28(H28), C42(H42), C38(H38), C43(H43),
  C35(H35), C12(H12), C36(H36), C25(H25), C52(H52), C24(H24), C23(H23),
 C13(H13), C30(H30), C48(H48), C11(H11), C49(H49), C37(H37), C29(H29), C54(H54),
  C50(H50), C58(H58), C57(H57), C53(H53), C59(H59), C02T(H02T), C02U(H02U),
 C02R(H02R), C02X(H02X), C02Y(H02Y), C032(H032), C033(H033), C035(H035),
 C031(H031), C030(H030), C74(H74), C02V(H02V), C51(H51), C73(H73), C72(H72),
 C4A(H4A), C76(H76), C3A(H3A), C2A(H2A), C1A(H1A), C80(H80), C79(H79), C77(H77),
  C81(H81), C40(H40)
5.b Fitted hexagon refined as free rotating group:
 C02W(C02T,C02U,C02R,C02X,C02Y), C032(C033,C035,C031,C030,C02Z), C75(C74,C02V,
 C51,C73,C72), C5A(C4A,C76,C3A,C2A,C1A), C80(C79,C77,C81,C78,C40)
5.c Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C), C034(H03A,H03B,H03C), C0(H0A,H0B,H0C)
;
_shelx_res_checksum              6742
_shelx_hkl_checksum              58272
_olex2_submission_special_instructions 'No special instructions were received'