A water-soluble naphthalenediimide-containing hexacationic cage.
Fang, Shuai; Li, Errui; Zhu, Dingsheng; Wu, Guangcheng; Zhang, Qinhao; Lin, Chuhao; Huang, Feihe; Li, Hao; Chemical communications (Cambridge, England) 57 (2021) 6074–6077; doi:10.1039/d1cc02242c

data_1562690
_publ_section_title
;
 A water-soluble naphthalenediimide-containing hexacationic cage.
;
_journal_issue                   49
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6074
_journal_page_last               6077
_journal_paper_doi               10.1039/d1cc02242c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety
'11.5(Br), H2 O, C90 H53 N12 O12, C9 H6 Br0.5 O4, 3(C9 H6 O4), C90 H55 N12 O12, C9 H5 O4, C8 H8 O3, O'
_chemical_formula_sum            'C233 H147 Br12 N24 O49'
_chemical_formula_weight         5025.66
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-09 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                99.495(9)
_cell_angle_beta                 108.239(7)
_cell_angle_gamma                105.860(7)
_cell_formula_units_Z            2
_cell_length_a                   21.620(3)
_cell_length_b                   25.189(3)
_cell_length_c                   26.682(3)
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.05
_cell_measurement_theta_min      2.80
_cell_volume                     12767(3)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_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  0.0968
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_number            48401
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.173
_diffrn_reflns_theta_min         2.770
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.943
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 235487 reflections, Rint = 0.0968
 (86795 with I > 3sig(I), Rint = 0.0790)
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             5050
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.849
_refine_diff_density_min         -1.323
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     2903
_refine_ls_number_reflns         48401
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1836
_refine_ls_R_factor_gt           0.1431
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+100.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3051
_refine_ls_wR_factor_ref         0.3198
_reflns_Friedel_coverage         0.000
_reflns_number_gt                25854
_reflns_number_total             48401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02242c2.cif
_cod_data_source_block           200909fs_1_0m
_cod_depositor_comments
'Adding full bibliography for 1562686--1562691.cif.'
_cod_original_cell_volume        12766(3)
_cod_database_code               1562690
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.892
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O50S-C50S
 1.2 with sigma of 0.02
 O53S-C56S
 1.2 with sigma of 0.02
 O52S-C52S
 1.4 with sigma of 0.02
 H51S-H115
 2 with sigma of 0.02
 H12S-H102
 2 with sigma of 0.02
 H22S-H55S_$1
 2 with sigma of 0.01
 C57S-O53S \\sim O53S-C55S
 with sigma of 0.02
 C51S-O50S \\sim O50S-O51S
 with sigma of 0.02
 C53S-O52S \\sim O52S-C51S
 with sigma of 0.02
3. Restrained planarity
 O53S, C55S, C56S, C57S
 with sigma of 0.1
 O50S, O51S, C50S, C51S
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O20S \\sim C22S \\sim C27S \\sim C26S \\sim C25S \\sim C24S \\sim C23S \\sim
C28S: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O51S \\sim C50S \\sim C51S \\sim C53S \\sim C54S \\sim C55S \\sim C56S \\sim
C57S \\sim C58S: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
O50S \\sim O51S \\sim O53S \\sim C50S \\sim C51S \\sim C53S \\sim C54S \\sim
C55S \\sim C56S \\sim C57S \\sim C58S: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
O52S \\sim C52S: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
C50S \\sim O51S \\sim C58S \\sim C57S \\sim C56S \\sim C55S \\sim C54S \\sim
C53S \\sim C52S \\sim C51S \\sim O52S \\sim O50S \\sim O53S: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O53S) \\sim Ueq, Uanis(O50S) \\sim Ueq, Uanis(C50S) \\sim Ueq,
Uanis(O51S) \\sim Ueq, Uanis(C51S) \\sim Ueq, Uanis(C58S) \\sim Ueq,
Uanis(C52S) \\sim Ueq, Uanis(C53S) \\sim Ueq, Uanis(C57S) \\sim Ueq,
Uanis(O52S) \\sim Ueq, Uanis(C54S) \\sim Ueq, Uanis(C56S) \\sim Ueq,
Uanis(C55S) \\sim Ueq, : with sigma of 0.005 and sigma for terminal atoms of
0.01
5. Others
 Fixed Sof: Br4(0.5) Br6(0.5) Br8(0.5) Br9(0.5) Br10(0.5) Br0A(0.5) Br00(0.5)
 Br11(0.5) Br12(0.5) Br02(0.5) Br13(0.5) Br07(0.5) Br15(0.5)
6.a Free rotating group:
 O00Z(H00A,H00B)
6.b :
 C52S(O51S,C50S,C51S,C53S,C54S,C55S,C56S,C57S,C58S)
6.c Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C39(H39A,H39B), C64(H64A,H64B), C65(H65A,H65B), C90(H90A,
 H90B), C97(H97A,H97B), C122(H12A,H12B), C129(H12C,H12D), C156(H15A,H15B),
 C157(H15C,H15D), C182(H18A,H18B)
6.d Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C12(H12), C15(H15), C16(H16), C22(H22), C28(H28), C29(H29), C30(H30), C31(H31),
  C34(H34), C36(H36), C38(H38), C40(H40), C41(H41), C42(H42), C44(H44),
 C47(H47), C48(H48), C53(H53), C54(H54), C60(H60), C61(H61), C62(H62), C63(H63),
  C66(H66), C67(H67), C68(H68), C70(H70), C73(H73), C74(H74), C79(H79),
 C80(H80), C86(H86), C87(H87), C88(H88), C89(H89), C2S(H2S), C5S(H5S), C6S(H6S),
  C8S(H8S), C11S(H11S), C14S(H14S), C15S(H15S), C17S(H17S), C92(H92), C94(H94),
 C96(H96), C98(H98), C99(H99), C100(H100), C102(H102), C108(H108), C109(H109),
 C115(H115), C116(H116), C118(H118), C119(H119), C120(H120), C121(H121),
 C124(H124), C126(H126), C128(H128), C130(H130), C131(H131), C132(H132),
 C134(H134), C137(H137), C138(H138), C144(H144), C145(H145), C152(H152),
 C153(H153), C154(H154), C155(H155), C158(H158), C159(H159), C160(H160),
 C162(H162), C165(H165), C166(H166), C174(H174), C175(H175), C178(H178),
 C179(H179), C180(H180), C181(H181), C21S(H21S), C27S(H27S), C25S(H25S),
 C24S(H24S), C31S(H31S), C34S(H34S), C35S(H35S), C37S(H37S), C42S(H42A),
 C43S(H43S), C45S(H45S), C51S(H51S), C54S(H54S), C55S(H55S), C57S(H57S)
6.e Fitted hexagon refined as free rotating group:
 C27S(C26S,C25S,C24S,C23S,C28S)
6.f Tetrahedral OH refined with riding coordinates:
 O52S(H52S)
6.g Idealised Me refined as rotating group:
 C47S(H47A,H47B,H47C)
6.h Idealised tetrahedral OH refined as rotating group:
 O3S(H3S), O4S(H4S), O12S(H12S), O13S(H13S), O19(H19), O22S(H22S), O23S(H23S),
 O33S(H33S), O41S(H41S), O42S(H42S), O53S(H53S)
;
_shelx_res_checksum              88118
_shelx_hkl_checksum              87391
_shelx_fab_checksum              44810
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'