Tetraphenylethene-based tetracationic cyclophanes and their selective recognition for amino acids and adenosine derivatives in water.
Cheng, Lin; Zhang, Haiyang; Dong, Yunhong; Zhao, Yanxia; Yu, Yang; Cao, Liping; Chemical communications (Cambridge, England) 55 (2019) 2372–2375; doi:10.1039/c9cc00599d

data_7125364
_publ_section_title
;
 Tetraphenylethene-based tetracationic cyclophanes and their selective
 recognition for amino acids and adenosine derivatives in water.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2372
_journal_page_last               2375
_journal_paper_doi               10.1039/c9cc00599d
_journal_volume                  55
_journal_year                    2019
_chemical_formula_moiety
'C56 H46 N4, 4(F6 P), (C H2 Cl2), 0.5(C H Cl3)'
_chemical_formula_sum            'C57.5 H48.5 Cl3.5 F24 N4 P4'
_chemical_formula_weight         1499.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-23 deposited with the CCDC.
2019-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.8044(17)
_cell_length_b                   13.8129(8)
_cell_length_c                   17.8677(10)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      23.54
_cell_measurement_theta_min      2.32
_cell_volume                     7107.0(7)
_computing_cell_refinement       'SAINT V.8.37A (Bruker AXS Inc., 2016)'
_computing_data_collection       'APEX3 v.2016.9-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V.8.37A (Bruker AXS Inc., 2016)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            79616
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.404
_diffrn_reflns_theta_min         2.280
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1135 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.9381. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             3028
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_platon_squeeze_details
;
In each unit cell, 4 dichloromethane and 2 trichloromethane
solvent molecules were found to be severely disordered and therefore 
removed by PLATON (Ver. 201118)'s SQUEEZE subroutine. Approximately 
280 electron equivalents were removed from the unit cell. 
The total void volume was 1804 ? indicated by PLATON, 
equivalent to 25.38 % of the unit cell?s total volume.
;
_refine_diff_density_max         0.880
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     903
_refine_ls_number_reflns         13052
_refine_ls_number_restraints     1587
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0998
_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^)+(0.1279P)^2^+20.2253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2686
_refine_ls_wR_factor_ref         0.2799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10040
_reflns_number_total             13052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00599d2.cif
_cod_data_source_block           1_a
_cod_original_sg_symbol_H-M      'P  21/c '
_cod_original_formula_sum        'C57.50 H48.50 Cl3.50 F24 N4 P4'
_cod_database_code               7125364
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{P3, P5}
3. Restrained distances
 F24-F18 \\sim P5-F18
 with sigma of 0.02
 N1-F18 \\sim F13A-F18
 with sigma of 0.02
 N2-F18 \\sim F14A-F18
 with sigma of 0.02
 N3-F18 \\sim F15A-F18
 with sigma of 0.02
 N4-F18 \\sim F16A-F18
 with sigma of 0.02
 P1-F18 \\sim F17A-F18
 with sigma of 0.02
 F19-F17 \\sim F18A-F17
 with sigma of 0.02
 F20-F17 \\sim F19A-F17
 with sigma of 0.02
 F21-F17 \\sim F20A-F17
 with sigma of 0.02
 F22-F17 \\sim F21A-F17
 with sigma of 0.02
 F23-F17 \\sim F22A-F17
 with sigma of 0.02
 P2-F17 \\sim F23A-F17
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
P3 \\sim F13 \\sim F14 \\sim F15 \\sim F17 \\sim F18 \\sim P5 \\sim F13A \\sim
F14A \\sim F15A \\sim F16A \\sim F17A \\sim F18A \\sim F19 \\sim F20 \\sim F21
\\sim F22 \\sim F23 \\sim F24 \\sim P4 \\sim F19A \\sim F20A \\sim F21A \\sim
F22A \\sim F23A \\sim F24A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
F19 \\sim F20 \\sim F21 \\sim F22 \\sim F23 \\sim F24 \\sim P4 \\sim F19A \\sim
F20A \\sim F21A \\sim F22A \\sim F23A \\sim F24A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
P3 \\sim F13 \\sim F14 \\sim F15 \\sim F16 \\sim F17 \\sim F18 \\sim P5 \\sim
F13A \\sim F14A \\sim F15A \\sim F16A \\sim F17A \\sim F18A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56 \\sim F1
\\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9 \\sim
F10 \\sim F11 \\sim F12 \\sim F19 \\sim F20 \\sim F21 \\sim F22 \\sim F23 \\sim
F24 \\sim N1 \\sim N2 \\sim N3 \\sim N4: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(P3) = Uanis(P5)
5. Rigid body (RIGU) restrains
 F19, F20, F21, F22, F23, F24, P4, F19A, F20A, F21A, F22A, F23A, F24A, P3, F13,
  F14, F15, F16, F17, F18, P5, F13A, F14A, F15A, F16A, F17A, F18A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17,
 C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33,
  C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44, C45, C46, C47, C48,
 C49, C50, C51, C52, C53, C54, C55, C56, F1, F2, F3, F4, F5, F6, F7, F8, F9,
 F10, F11, F12, F19, F20, F21, F22, F23, F24, N1, N2, N3, N4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F19A)=Sof(F20A)=Sof(F21A)=Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(1)
 Sof(F19)=Sof(F20)=Sof(F21)=Sof(F22)=Sof(F23)=Sof(F24)=FVAR(1)
 Sof(P5)=Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(2)
 Sof(P3)=Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=Sof(F17)=Sof(F18)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C39(H39A,H39B), C46(H46A,H46B)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25),
  C26(H26), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C41(H41), C42(H42), C44(H44), C45(H45), C47(H47), C48(H48),
  C50(H50), C51(H51), C53(H53), C54(H54), C55(H55), C56(H56)
;
_shelx_res_checksum              19836
_shelx_fab_checksum              19990
_olex2_submission_special_instructions 'No special instructions were received'