Discrete Open-Shell Tris(bipyridinium radical cationic) Inclusion Complexes in the Solid State
Anamimoghadam, Ommid; Jones, Leighton O.; Cooper, James A.; Beldjoudi, Yassine; Nguyen, Minh T.; Liu, Wenqi; Krzyaniak, Matthew D.; Pezzato, Cristian; Stern, Charlotte L.; Patel, Hasmukh A.; Wasielewski, Michael R.; Schatz, George C.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c07148

data_4135421
_publ_section_title
;
 Discrete Open-Shell Tris(bipyridinium radical cationic) Inclusion
 Complexes in the Solid State
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c07148
_journal_year                    2020
_chemical_formula_moiety
'3(F6 P), C40 H40 N4 O4, C12 H14 N2, 4(C2 H3 N)'
_chemical_formula_sum            'C60 H66 F18 N10 O4 P3'
_chemical_formula_weight         1426.13
_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     direct
_audit_creation_date             2020-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                112.345(3)
_cell_angle_beta                 98.076(3)
_cell_angle_gamma                113.601(3)
_cell_formula_units_Z            1
_cell_length_a                   12.1780(7)
_cell_length_b                   12.6271(7)
_cell_length_c                   12.8582(7)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.91
_cell_measurement_theta_min      2.49
_cell_volume                     1572.70(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29448
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.108
_diffrn_reflns_theta_max         25.108
_diffrn_reflns_theta_min         1.945
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1125 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.9316.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       block
_exptl_crystal_F_000             735
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     624
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+4.0874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4362
_reflns_number_total             5575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c07148_si_007.cif
_cod_data_source_block           a
_cod_original_cell_volume        1572.70(16)
_cod_database_code               4135421
_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
 F7-F9 \\sim F7-F8 \\sim F7-F5 \\sim F7-F6 \\sim F9-F8 \\sim F9-F6 \\sim F9-F4
\\sim F9A-F4A \\sim F9A-F6A ~
 F9A-F8A \\sim F9A-F7A \\sim F4A-F6A \\sim F4A-F5A \\sim F4A-F8A \\sim F6A-F5A
\\sim F6A-F7A \\sim F8-F5 ~
 F8-F4 \\sim F5A-F8A \\sim F5A-F7A \\sim F8A-F7A \\sim F5-F6 \\sim F5-F4 \\sim
F6-F4
 with sigma of 0.04
 P2-F7 \\sim P2-F9 \\sim P2-F9A \\sim P2-F4A \\sim P2-F6A \\sim P2-F8 \\sim
P2-F5A \\sim P2-F8A \\sim P2-F7A ~
 P2-F5 \\sim P2-F6 \\sim P2-F4
 with sigma of 0.02
3. Rigid bond restraints
 F7, P2, F9, F4A, F9A, F6A, F8, F5, F5A, F8A, F7A, F6, F4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F7 \\sim P2 \\sim F9 \\sim F4A \\sim F9A \\sim F6A \\sim F8 \\sim F5 \\sim F5A
\\sim F8A \\sim F7A \\sim F6 \\sim F4: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(F7) \\sim Ueq, Uanis(P2) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F4A) \\sim
Ueq, Uanis(F9A) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F5)
\\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F7A) \\sim Ueq,
Uanis(F6) \\sim Ueq, Uanis(F4) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
5. Others
 Fixed Sof: F4A(0.65) F6A(0.65) F3A(0.65) F8A(0.65) F7A(0.65) F2A(0.65)
 F9A(0.65) F5A(0.65) F2(0.35) F3(0.35) F5(0.35) F6(0.35) F7(0.35) F8(0.35)
 F4(0.35) F9(0.35)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C1(H1A,H1B)
6.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C4(H4), C19(H19), C17(H17), C25(H25), C14(H14), C22(H22),
 C21(H21), C18(H18), C11(H11), C12(H12), C20(H20), C23(H23)
6.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C), C3(H3A,H3B,H3C), C29(H29A,H29B,
 H29C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              40124
_shelx_hkl_checksum              33654
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'