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_1562691
_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_absolute_configuration rmad
_chemical_formula_moiety         '6(Br), C90 H53 N12 O12, C10 H8 O, 2(H2 O)'
_chemical_formula_sum            'C100 H65 Br6 N12 O15'
_chemical_formula_weight         2154.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-24
_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                90
_cell_angle_beta                 108.666(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.8016(17)
_cell_length_b                   21.9859(17)
_cell_length_c                   28.453(2)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.50
_cell_measurement_theta_min      3.43
_cell_volume                     11143.0(16)
_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      170.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.2021
_diffrn_reflns_av_unetI/netI     0.3486
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            45398
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.635
_diffrn_reflns_theta_min         3.424
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.125
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.3374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1770 before and 0.1047 after correction. The Ratio of minimum to maximum transmission is 0.4494. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             4316
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.015
_refine_diff_density_max         3.262
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.248
_refine_ls_abs_structure_details
;
 Flack x determined using 695 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     1044
_refine_ls_number_reflns         19832
_refine_ls_number_restraints     983
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.2889
_refine_ls_R_factor_gt           0.1777
_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^)+(0.0500P)^2^+100.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3724
_refine_ls_wR_factor_ref         0.4512
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                6839
_reflns_number_total             19832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02242c2.cif
_cod_data_source_block           mj19808_0m
_cod_depositor_comments
'Adding full bibliography for 1562686--1562691.cif.'
_cod_original_cell_volume        11142.9(16)
_cod_database_code               1562691
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.959
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 O13-C102
 1.42 with sigma of 0.02
 Br1-H97
 2.2 with sigma of 0.02
 C102-C101 = C93-C102 = C94-C93 = C99-C94 = C99-C100 = C101-C100 = C99-C98 =
 C98-C97 = C97-C96 = C96-C95 = C95-C94
 1.39 with sigma of 0.02
 N11-C92
 1.5 with sigma of 0.01
 C101-O13 \\sim O13-C93
 with sigma of 0.02
3. Restrained planarity
 O13, C93, C101, C102
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C22 \\sim C23: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C40 \\sim C41 \\sim C42: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C94 \\sim C95 \\sim C96 \\sim C97 \\sim C98 \\sim C99 \\sim C100: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97 \\sim C98 \\sim C99 \\sim C100
\\sim C101 \\sim C102: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
N3 \\sim C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
O13 \\sim C93 \\sim C94 \\sim C95 \\sim C96 \\sim C97 \\sim C98 \\sim C99 \\sim
C100 \\sim C101 \\sim C102: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C14 \\sim O1 \\sim C50 \\sim N4 \\sim C49 \\sim C51 \\sim C59 \\sim C57 \\sim
C48 \\sim O2 \\sim C52 \\sim C60 \\sim C61 \\sim C56 \\sim C47 \\sim C53 \\sim
N3 \\sim C62 \\sim C46 \\sim C55 \\sim C54 \\sim C63 \\sim C64 \\sim C45 \\sim
C58 \\sim C1 \\sim O3 \\sim N7 \\sim O4 \\sim C2 \\sim C6 \\sim C43 \\sim C3
\\sim C5 \\sim C44 \\sim C42 \\sim C4 \\sim C7 \\sim C65 \\sim N10 \\sim C41
\\sim N1 \\sim N2 \\sim C40 \\sim C39 \\sim C8 \\sim C12 \\sim C66 \\sim C70
\\sim C35 \\sim C9 \\sim C11 \\sim C67 \\sim C69 \\sim C34 \\sim C36 \\sim C10
\\sim N6 \\sim C68 \\sim N5 \\sim C33 \\sim C37 \\sim C26 \\sim C13 \\sim C86
\\sim C72 \\sim C32 \\sim C38 \\sim C92 \\sim O9 \\sim C23 \\sim O10 \\sim O5
\\sim C83 \\sim O0AA \\sim C73 \\sim N12 \\sim N11 \\sim C22 \\sim C24 \\sim
C15 \\sim C82 \\sim C84 \\sim C74 \\sim C28 \\sim C31 \\sim C88 \\sim C91 \\sim
C21 \\sim C25 \\sim C16 \\sim C81 \\sim C85 \\sim C75 \\sim C27 \\sim C30 \\sim
C87 \\sim C90 \\sim C20 \\sim C17 \\sim C80 \\sim C76 \\sim N9 \\sim C29 \\sim
N8 \\sim C89 \\sim C19 \\sim C18 \\sim C79 \\sim C77 \\sim O11 \\sim O12 \\sim
O8 \\sim O7: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C50) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C79) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C26) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C13)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C35) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C92) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(O6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: Br2A(0.5) Br1(0.5) Br3(0.5) Br7(0.5)
6.a Free rotating group:
 O14(H14A,H14B), O6(H6A,H6B)
6.b :
 C98(C93,C94,C95,C96,C97,C99,C100,C101,C102)
6.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C32(H32A,H32B), C39(H39A,H39B), C64(H64A,H64B), C65(H65A,H65B),
 C92(H92A,H92B)
6.d Aromatic/amide H refined with riding coordinates:
 C44(H44), C42(H42), C41(H41), C40(H40), C2(H2), C4(H4), C6(H6), C10(H10),
 C9(H9), C8(H8), C12(H12), C15(H15), C16(H16), C21(H21), C22(H22), C28(H28),
 C31(H31), C30(H30), C29(H29), C34(H34), C38(H38), C36(H36), C47(H47), C48(H48),
  C53(H53), C54(H54), C60(H60), C63(H63), C62(H62), C61(H61), C68(H68),
 C67(H67), C66(H66), C74(H74), C75(H75), C81(H81), C82(H82), C88(H88), C91(H91),
  C90(H90), C89(H89), C98(H98), C93(H93), C95(H95), C96(H96), C97(H97),
 C100(H100), C101(H101)
6.e Fitted hexagon refined as free rotating group:
 N4(C51,C52,C57,C49,C50), N10(C44,C43,C42,C41,C40), C2(C3,C4,C5,C6,C1),
 C11(C10,C9,C8,N1,C12), C25(C20,C19,N9,C18,C17), C26(C23,C24,C14,C13,N6),
 C27(C28,N12,C31,C30,C29), C35(C34,C33,C38,C37,C36), C59(C60,N3,C63,C62,C61),
 C69(C68,C67,C66,N2,C70), C84(C83,C86,N5,C72,C73), C85(C76,C77,N8,C79,C80),
 C87(C88,N11,C91,C90,C89)
6.f Tetrahedral OH refined with riding coordinates:
 O13(H13)
;
_shelx_res_checksum              5436
_shelx_hkl_checksum              65515
_shelx_fab_checksum              84455
_olex2_submission_special_instructions 'No special instructions were received'