Selective recognition and enrichment of C70 over C60 using an anthracene-based nanotube
Nian, Hao; Wang, Song-Meng; Wang, Yan-Fang; Zheng, Yu-Tao; Zheng, Li-Shuo; Wang, Xiaoping; Yang, Liu-Pan; Jiang, Wei; Cao, Liping; Chemical Science 15 (2024) 10214–10220; doi:10.1039/D4SC02814G

data_1571761
_publ_section_title
;
 Selective recognition and enrichment of C70 over C60 using an
 anthracene-based nanotube
;
_journal_issue                   26
_journal_name_full               'Chemical Science'
_journal_page_first              10214
_journal_page_last               10220
_journal_paper_doi               10.1039/D4SC02814G
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety
'2(C2 H F3 O2), C126 H90 N3 O9, 3(C2 F3 O2), 4(C7 H8)'
_chemical_formula_sum            'C164 H124 F15 N3 O19'
_chemical_formula_weight         2725.65
_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             2022-11-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2024-01-03 deposited with the CCDC.	2024-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                87.108(3)
_cell_angle_beta                 89.657(2)
_cell_angle_gamma                86.001(3)
_cell_formula_units_Z            2
_cell_length_a                   11.7820(6)
_cell_length_b                   18.0992(10)
_cell_length_c                   38.789(2)
_cell_measurement_reflns_used    9813
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      44.232
_cell_measurement_theta_min      2.305
_cell_volume                     8240.9(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_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           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            178709
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.034
_diffrn_reflns_theta_min         1.984
_diffrn_source_current           3.0
_diffrn_source_power             0.20955
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1061 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.9063.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       plate
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1896
_refine_ls_number_reflns         33623
_refine_ls_number_restraints     477
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0904
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1816P)^2^+0.8818P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2784
_refine_ls_wR_factor_ref         0.3228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16951
_reflns_number_total             33623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02814g2.cif
_cod_data_source_block           p-1
_cod_depositor_comments          'Adding full bibliography for 1571761.cif.'
_cod_original_cell_volume        8240.8(8)
_cod_database_code               1571761
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C1-F6
 1.27 with sigma of 0.02
 C2-F3
 1.29 with sigma of 0.02
 C2-F4
 1.36 with sigma of 0.02
 C2-F5
 1.27 with sigma of 0.02
 C1-F1
 1.29 with sigma of 0.02
 C1-F2
 1.36 with sigma of 0.02
 C04M-C052
 1.45 with sigma of 0.02
 C6-C7 = C8-C9 = C9-C10
 1.38 with sigma of 0.02
 C5-C6 = C5-C10 = C7-C8
 1.39 with sigma of 0.02
 C4-C5
 1.51 with sigma of 0.02
 C13-C14 = C15-C16 = C16-C17
 1.38 with sigma of 0.02
 C12-C13 = C12-C17 = C14-C15
 1.39 with sigma of 0.02
 C11-C12
 1.51 with sigma of 0.02
 F8-C19
 1.33 with sigma of 0.02
 C18-C19
 1.55 with sigma of 0.02
 F7-C19 = F9-C19
 1.34 with sigma of 0.02
 O5-C18
 1.25 with sigma of 0.02
 O6-C18
 1.24 with sigma of 0.02
 O024-C21
 1.4 with sigma of 0.02
 C6-C8
 2.39 with sigma of 0.04
 C5-C9
 2.41 with sigma of 0.04
 C7-C9 = C8-C10
 2.4 with sigma of 0.04
 C4-C6 = C4-C10
 2.52 with sigma of 0.04
 C5-C7
 2.42 with sigma of 0.04
 C11-C13 = C11-C17
 2.52 with sigma of 0.04
 C12-C14
 2.42 with sigma of 0.04
 C12-C16
 2.41 with sigma of 0.04
 C13-C15
 2.39 with sigma of 0.04
 C14-C16 = C15-C17
 2.4 with sigma of 0.04
 O5-C19
 2.38 with sigma of 0.04
 F8-C18
 2.42 with sigma of 0.04
 O5-O6
 2.25 with sigma of 0.04
 O6-C19
 2.35 with sigma of 0.04
 F9-C18
 2.39 with sigma of 0.04
 F7-F9
 2.15 with sigma of 0.04
 F7-F8 = F8-F9
 2.16 with sigma of 0.04
 F7-C18
 2.37 with sigma of 0.04
 F3-F4 \\sim F4-F5 \\sim F5-F3
 with sigma of 0.03
 F1-F2 \\sim F2-F6 \\sim F6-F1
 with sigma of 0.03
 C2-F3 \\sim C2-F4 \\sim C2-F5
 with sigma of 0.02
 C1-F1 \\sim C1-F2 \\sim C1-F6
 with sigma of 0.02
 C5-C9 \\sim C5-C7 \\sim C10-C8 \\sim C6-C10 \\sim C7-C9 \\sim C6-C8
 with sigma of 0.04
 C4-C10 \\sim C4-C6
 with sigma of 0.04
 C5-C6 \\sim C6-C7 \\sim C7-C8 \\sim C8-C9 \\sim C9-C10 \\sim C10-C5
 with sigma of 0.02
 C11-C17 \\sim C11-C13
 with sigma of 0.04
 C12-C13 \\sim C13-C14 \\sim C14-C15 \\sim C15-C16 \\sim C16-C17 \\sim C17-C12
 with sigma of 0.02
 C12-C16 \\sim C12-C14 \\sim C17-C15 \\sim C13-C17 \\sim C14-C16 \\sim C13-C15
 with sigma of 0.04
 C19-F7 \\sim C19-F8 \\sim C19-F9
 with sigma of 0.02
 C18-F7 \\sim C18-F8 \\sim C18-F9
 with sigma of 0.04
 F7-F8 \\sim F8-F9 \\sim F9-F7
 with sigma of 0.04
 C18-O6 \\sim C18-O5
 with sigma of 0.02
 O5-C18 \\sim O5A-C18A
 with sigma of 0.02
 O6-C19 \\sim O6A-C19A
 with sigma of 0.04
 O6-C18 \\sim O6A-C18A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 F7-C18 \\sim F7A-C18A
 with sigma of 0.04
 F9-C19 \\sim F9A-C19A
 with sigma of 0.02
 F7-C19 \\sim F7A-C19A
 with sigma of 0.02
 F7-F8 \\sim F7A-F8A
 with sigma of 0.04
 F7-F9 \\sim F7A-F9A
 with sigma of 0.04
 F9-C18 \\sim F9A-C18A
 with sigma of 0.04
 O5-O6 \\sim O5A-O6A
 with sigma of 0.04
 O5-C19 \\sim O5A-C19A
 with sigma of 0.04
 F8-C19 \\sim F8A-C19A
 with sigma of 0.02
 F8-F9 \\sim F8A-F9A
 with sigma of 0.04
 F8-C18 \\sim F8A-C18A
 with sigma of 0.04
3. Restrained planarity
 C4, C5, C6, C7, C8, C9, C10
 with sigma of 0.1
 C11, C12, C13, C14, C15, C16, C17
 with sigma of 0.1
 C18, C19, O5, O6
 with sigma of 0.1
4. Rigid bond restraints
 C01X, C02A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C021, C02A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C023, C03G
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C01X, C026
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
5. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
F7 \\sim F8 \\sim F9 \\sim O5 \\sim O6 \\sim C18 \\sim C19: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(F7A) \\sim Ueq, Uanis(F9A) \\sim Ueq, Uanis(F8A) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
Uanis(C19A) \\sim Ueq, Uanis(C18A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F9A) = Uanis(F8A)
Uanis(C21) = Uanis(C3)
6. Rigid body (RIGU) restrains
 C4, C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, C12, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F7, F8, F9, O5, O6, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Fixed Sof: C2(0.5) F3(0.5) F4(0.5) F5(0.5) C1(0.5) F1(0.5) F2(0.5) F6(0.5)
 C3(0.75) H3A(0.75) H3B(0.75) H3C(0.75) F7(0.75) F8(0.75) F9(0.75) O5(0.75)
 O6(0.75) C18(0.75) C19(0.75) C21(0.25) H21A(0.25) H21B(0.25) H21C(0.25)
 F7A(0.25) C19A(0.25) F8A(0.25) F9A(0.25) C18A(0.25) O6A(0.25) O5A(0.25)
8.a Aromatic/amide H refined with riding coordinates:
 N00H(H00H), N00J(H00J), N00M(H00M), C016(H016), C017(H017), C019(H019),
 C01A(H01A), C01F(H01F), C01K(H01K), C01Y(H01Y), C020(H020), C023(H023),
 C027(H027), C028(H028), C02I(H02I), C02L(H02L), C02P(H02P), C02Q(H02Q),
 C02W(H02W), C02Y(H02Y), C02Z(H02Z), C031(H031), C032(H032), C035(H035),
 C037(H037), C039(H039), C03A(H03G), C03C(H03H), C03F(H03L), C03G(H03M),
 C03H(H03N), C03I(H03O), C03J(H03P), C03L(H03Q), C03M(H03R), C03N(H03S),
 C03O(H03T), C03P(H03U), C03Q(H03V), C03U(H03W), C03V(H03X), C03W(H03Y),
 C03Y(H03Z), C03Z(H03), C041(H041), C042(H042), C044(H044), C045(H045),
 C046(H046), C04A(H04G), C04B(H04H), C04C(H04I), C04D(H04J), C04E(H04K),
 C04F(H04L), C04G(H04M), C04H(H04N), C04K(H04O), C04N(H04P), C04R(H04R),
 C04T(H04T), C04V(H04V), C058(H058), C059(H059), C04J(H04Q), C04U(H04U),
 C04Y(H04Y), C04Z(H04Z), C050(H050), C04Q(H04S), C03T(H1), C04W(H04W),
 C053(H053), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
8.b Fitted hexagon refined as free rotating group:
 C04T(C04M,C04V,C058,C059,C04J), C04Z(C050,C04Q,C03T,C04I,C04W)
8.c Tetrahedral OH refined with riding coordinates:
 O00E(H00E), O00P(H00P)
8.d Idealised Me refined as rotating group:
 C02M(H02A,H02B,H02C), C02U(H02D,H02E,H02F), C02X(H02G,H02H,H02J), C030(H03A,
 H03B,H03C), C036(H03D,H03E,H03F), C03E(H03I,H03J,H03K), C043(H04A,H04B,H04C),
 C048(H04D,H04E,H04F), C052(H05A,H05B,H05C), C05B(H05D,H05E,H05F), C3(H3A,H3B,
 H3C), C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              22035
_shelx_hkl_checksum              97678
_shelx_fab_checksum              92409
_olex2_submission_special_instructions 'No special instructions were received'