Phosphonium fullerides: isolable zwitterionic adducts of a phosphine with C<sub>60</sub>.
Röthel, Maike B; Franzen, Jonas H.; Leitner, Daniel; Hofer, Thomas S.; Seidl, Michael; Dielmann, Fabian; Chemical science 16 (2025) 13189–13195; doi:10.1039/d5sc00367a

data_1574951
_publ_section_title
;
 Phosphonium fullerides: isolable zwitterionic adducts of a phosphine with
 C<sub>60</sub>.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              13189
_journal_page_last               13195
_journal_paper_doi               10.1039/d5sc00367a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C79 H44 N9 O P'
_chemical_formula_sum            'C79 H44 N9 O P'
_chemical_formula_weight         1166.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-12-18 deposited with the CCDC.	2025-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6389(4)
_cell_length_b                   13.6916(5)
_cell_length_c                   23.9526(9)
_cell_measurement_reflns_used    9810
_cell_measurement_temperature    153.00
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.61
_cell_volume                     5128.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker, Apex4 2021'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      153.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            114077
_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         28.319
_diffrn_reflns_theta_min         2.142
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0694 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.9097.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1254
_refine_ls_number_reflns         6641
_refine_ls_number_restraints     1885
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0891P)^2^+3.0650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1673
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5130
_reflns_number_total             6641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00367a2.cif
_cod_data_source_block           fd23_21w
_cod_depositor_comments          'Adding full bibliography for 1574951.cif.'
_cod_database_code               1574951
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24B-C23B = C8B-C24B = C8B-C7B = C7B-C21B = C22B-C21B = C23B-C22B
 1.38 with sigma of 0.02
 C9B-C26B = C9B-C8B = C8B-C24B = C25B-C24B = C26B-C25B
 1.38 with sigma of 0.02
 C44B-C25B = C44B-C58B = C44B-C46B = C44B-C27B = C43B-C41B = C43B-C26B = C43B-
 C24B = C42B-C55B = C42B-C23B = C42B-C40B = C56B-C58B = C56B-C54B = C56B-C60B =
 C57B-C47B = C57B-C59B = C58B-C46B = C58B-C60B = C47B-C45B = C47B-C29B = C47B-
 C31B = C46B-C30B = C45B-C26B = C27B-C25B = C27B-C9B = C27B-C11B = C26B-C10B =
 C25B-C23B = C24B-C41B = C24B-C22B = C24B-C7B = C23B-C21B = C41B-C54B = C40B-
 C55B = C40B-C53B = C40B-C38B = C54B-C37B = C55B-C59B = C60B-C49B = C60B-C51B =
 C59B-C50B = C49B-C31B = C49B-C51B = C49B-C33B = C48B-C30B = C48B-C32B = C31B-
 C29B = C31B-C33B = C30B-C28B = C30B-C12B = C29B-C11B = C28B-C10B = C28B-C12B =
 C11B-C9B = C11B-C13B = C10B-C8B = C10B-C6B = C9B-C7B = C8B-C21B = C8B-C6B =
 C7B-C22B = C21B-C39B = C21B-C19B = C22B-C38B = C39B-C37B = C39B-C19B = C38B-
 C53B = C38B-C20B = C37B-C52B = C37B-C35B = C53B-C51B = C52B-C50B = C52B-C35B =
 C51B-C36B = C50B-C32B = C33B-C14B = C33B-C16B = C32B-C15B = C14B-C12B = C14B-
 C16B = C14B-C3B = C13B-C2B = C12B-C3B = C2B-C6B = C2B-C15B = C2B-C4B = C6B-C4B
 = C5B-C19B = C5B-C3B = C5B-C17B = C20B-C18B = C19B-C17B = C18B-C35B = C18B-
 C16B = C18B-C4B = C36B-C34B = C35B-C16B = C34B-C15B = C34B-C17B
 2.47 with sigma of 0.04
 C50-C49 \\sim C59-C49 \\sim C60-C59 \\sim C60-C52 \\sim C52-C51 \\sim C51-C50
 with sigma of 0.02
 C37B-C36B \\sim C36B-C18B \\sim C19B-C18B \\sim C38B-C19B \\sim C38B-C37B
 with sigma of 0.02
 C54B-C53B \\sim C54B-C40B \\sim C40B-C39B \\sim C39B-C38B \\sim C38B-C37B
\\sim C53B-C37B
 with sigma of 0.02
 C34B-C16B \\sim C34B-C33B \\sim C33B-C32B \\sim C32B-C14B \\sim C15B-C14B
\\sim C16B-C15B
 with sigma of 0.02
 C32B-C14B \\sim C32B-C31B \\sim C14B-C13B \\sim C31B-C30B \\sim C30B-C13B
 with sigma of 0.02
 C24B-C23B \\sim C25B-C24B
 with sigma of 0.02
 C46B-C29B \\sim C48B-C31B
 with sigma of 0.02
 C51B-C50B \\sim C60B-C59B
 with sigma of 0.02
 C59B-C51B \\sim C50B-C60B
 with sigma of 0.02
 C15B-C33B \\sim C34B-C14B
 with sigma of 0.02
 C4-C3 \\sim C3-C13 \\sim C14-C13 \\sim C4-C15 \\sim C15-C14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim C9: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
C10B \\sim C9B \\sim C1 \\sim C11B \\sim C12B: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 C1, C44B, C43B, C42B, C56B, C57B, C58B, C47B, C46B, C45B, C27B, C26B, C25B,
 C24B, C23B, C41B, C40B, C54B, C55B, C60B, C59B, C49B, C48B, C31B, C30B, C29B,
 C28B, C11B, C10B, C9B, C8B, C7B, C21B, C22B, C39B, C38B, C37B, C53B, C52B,
 C51B, C50B, C33B, C32B, C14B, C13B, C12B, C2B, C6B, C5B, C20B, C19B, C18B,
 C36B, C35B, C34B, C16B, C15B, C3B, C4B, C17B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C19, C7, C6, C5, C18, C17, C37, C38, C20, C21, C22, C8, C9, C2, C3, C4, C15,
 C16, C35, C36, C53, C54, C39, C40, C41, C42, C23, C24, C25, C26, C11, C12, C29,
  C30, C13, C14, C33, C34, C51, C52, C60, C55, C56, C57, C43, C44, C45, C27,
 C28, C48, C31, C32, C50, C49, C59, C58, C46, C47, C10, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H64A(0.5) H64B(0.5) H64C(0.5) H63A(0.5) H63B(0.5) H63C(0.5)
 C62(0.5) H62A(0.5) H62B(0.5) H62C(0.5) C65(0.5) H65A(0.5) H65B(0.5) H65C(0.5)
 C19(0.3) C7(0.3) C6(0.3) C5(0.3) C18(0.3) C17(0.3) C37(0.3) C38(0.3) C20(0.3)
 C21(0.3) C22(0.3) C8(0.3) C9(0.3) C10(0.3) C2(0.3) C3(0.3) C4(0.3) C15(0.3)
 C16(0.3) C35(0.3) C36(0.3) C53(0.3) C54(0.3) C39(0.3) C40(0.3) C41(0.3)
 C42(0.3) C23(0.3) C24(0.3) C25(0.3) C26(0.3) C11(0.3) C12(0.3) C29(0.3)
 C30(0.3) C13(0.3) C14(0.3) C33(0.3) C34(0.3) C51(0.3) C52(0.3) C60(0.3)
 C55(0.3) C56(0.3) C57(0.3) C43(0.3) C44(0.3) C45(0.3) C27(0.3) C28(0.3)
 C48(0.3) C31(0.3) C32(0.3) C50(0.3) C49(0.3) C59(0.3) C58(0.3) C46(0.3)
 C47(0.3) C44B(0.2) C43B(0.2) C42B(0.2) C56B(0.2) C57B(0.2) C58B(0.2) C47B(0.2)
 C46B(0.2) C45B(0.2) C27B(0.2) C26B(0.2) C25B(0.2) C24B(0.2) C23B(0.2)
 C41B(0.2) C40B(0.2) C54B(0.2) C55B(0.2) C60B(0.2) C59B(0.2) C49B(0.2)
 C48B(0.2) C31B(0.2) C30B(0.2) C29B(0.2) C28B(0.2) C11B(0.2) C10B(0.2) C9B(0.2)
 C8B(0.2) C7B(0.2) C21B(0.2) C22B(0.2) C39B(0.2) C38B(0.2) C37B(0.2) C53B(0.2)
 C52B(0.2) C51B(0.2) C50B(0.2) C33B(0.2) C32B(0.2) C14B(0.2) C13B(0.2)
 C12B(0.2) C2B(0.2) C6B(0.2) C5B(0.2) C20B(0.2) C19B(0.2) C18B(0.2) C36B(0.2)
 C35B(0.2) C34B(0.2) C16B(0.2) C15B(0.2) C3B(0.2) C4B(0.2) C17B(0.2) O1(0.5)
 C74(0.5) H74A(0.5) H74B(0.5) C73(0.5) H73A(0.5) H73B(0.5) C72(0.5) H72A(0.5)
 H72B(0.5) C71(0.5) H71A(0.5) H71B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C74(H74A,H74B), C73(H73A,H73B), C72(H72A,H72B), C71(H71A,H71B)
6.b Idealised Me refined as rotating group:
 C64(H64A,H64B,H64C), C70(H70A,H70B,H70C), C69(H69A,H69B,H69C), C67(H67A,H67B,
 H67C), C63(H63A,H63B,H63C), C68(H68A,H68B,H68C), C62(H62A,H62B,H62C), C65(H65A,
 H65B,H65C)
;
_shelx_res_checksum              81191
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems, Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'