A Dynamic Tetracationic Macrocycle Exhibiting Photoswitchable Molecular Encapsulation.
Wu, Huang; Chen, Yong; Zhang, Long; Anamimoghadam, Ommid; Shen, Dengke; Liu, Zhichang; Cai, Kang; Pezzato, Cristian; Stern, Charlotte L.; Liu, Yu; Stoddart, J. Fraser; Journal of the American Chemical Society 141 (2019) 1280–1289; doi:10.1021/jacs.8b10526

data_4133510
_publ_section_title
;
 A Dynamic Tetracationic Macrocycle Exhibiting Photoswitchable Molecular
 Encapsulation.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1280
_journal_page_last               1289
_journal_paper_doi               10.1021/jacs.8b10526
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety
'C58 H48 N4, 1.75(C20 H12), 4(F6 P1), 4(C2 H3 N)'
_chemical_formula_sum            'C101 H81 F24 N8 P4'
_chemical_formula_weight         1986.61
_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             2018-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                98.837(4)
_cell_angle_beta                 103.690(4)
_cell_angle_gamma                102.785(4)
_cell_formula_units_Z            2
_cell_length_a                   10.6321(6)
_cell_length_b                   21.0128(14)
_cell_length_c                   22.5307(15)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.83
_cell_measurement_theta_min      2.21
_cell_volume                     4655.3(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      99.97
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            53265
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        65.204
_diffrn_reflns_theta_max         65.204
_diffrn_reflns_theta_min         2.068
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.632
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1104 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.7809. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       needle
_exptl_crystal_F_000             2038
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.612
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.838
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1881
_refine_ls_number_reflns         15628
_refine_ls_number_restraints     2278
_refine_ls_restrained_S_all      1.788
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.1212
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3998
_refine_ls_wR_factor_ref         0.4153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12527
_reflns_number_total             15628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10526_si_007.cif
_cod_data_source_block           cx1273
_cod_database_code               4133510
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.453
_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
 C98-C99 \\sim C97-C98 \\sim C97-C96 \\sim C96-C108 \\sim C108-C100 \\sim
C100-C99 \\sim C101-C100 ~
 C102-C101 \\sim C103-C102 \\sim C103-C104 \\sim C108-C104 \\sim C105-C104
\\sim C106-C105 \\sim C106-
 C89 \\sim C90-C89 \\sim C90-C91 \\sim C107-C91 \\sim C107-C105 \\sim C96-C95
\\sim C94-C95 \\sim C107-C95
 \\sim C92-C91 \\sim C92-C93 \\sim C93-C94
 with sigma of 0.01
 C97-C96 \\sim C98-C97 \\sim C99-C98 \\sim C99-C100 \\sim C108-C100 \\sim
C96-C108 \\sim C108-C104 ~
 C96-C95 \\sim C95-C107 \\sim C107-C105 \\sim C105-C104 \\sim C91-C107 \\sim
C92-C91 \\sim C93-C92 ~
 C94-C93 \\sim C95-C94 \\sim C91-C90 \\sim C90-C89 \\sim C89-C106 \\sim
C106-C105 \\sim C104-C103 ~
 C103-C102 \\sim C102-C101 \\sim C101-C100
 with sigma of 0.01
 C96-C98 \\sim C97-C99 \\sim C100-C104 \\sim C108-C103 \\sim C105-C95 \\sim
C107-C92 \\sim C91-C93 ~
 C90-C106
 with sigma of 0.01
 C74A-C73A \\sim C73A-C72A \\sim C77A-C72A \\sim C77A-C76A \\sim C76A-C75A
\\sim C75A-C74A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C107 \\sim C95 \\sim C96 \\sim C94 \\sim C97 \\sim C108 \\sim C93 \\sim C91
\\sim C105 \\sim C98 \\sim C100 \\sim C104 \\sim C92 \\sim C90 \\sim C106 \\sim
C99 \\sim C101 \\sim C103 \\sim C89 \\sim C102: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02
Uanis(C105) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C106)
\\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C92) \\sim Ueq, Uanis(C107) \\sim Ueq,
Uanis(C104) \\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C95) \\sim Ueq, Uanis(C103)
\\sim Ueq, Uanis(C108) \\sim Ueq, Uanis(C94) \\sim Ueq, Uanis(C96) \\sim Ueq,
Uanis(C102) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C101)
\\sim Ueq, Uanis(C99) \\sim Ueq, Uanis(C98) \\sim Ueq, : with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=
 Sof(C8A)=Sof(H8A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C36A)=Sof(H36A)=Sof(C37A)=
 Sof(H37A)=Sof(C39A)=Sof(H39A)=Sof(C38A)=Sof(C43A)=Sof(H43A)=Sof(C42A)=
 Sof(H42A)=Sof(C41A)=Sof(C40A)=Sof(H40A)=Sof(C44A)=Sof(H44A)=Sof(C45A)=
 Sof(H45A)=1-FVAR(1)
 Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(H11)=Sof(C12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(C16)=
 Sof(H16)=Sof(C17)=Sof(H17)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=Sof(C41)=
 Sof(C40)=Sof(H40)=Sof(C39)=Sof(H39)=Sof(C38)=Sof(C43)=Sof(H43)=Sof(C42)=
 Sof(H42)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=FVAR(1)
 Sof(C59A)=Sof(C60A)=Sof(H60A)=Sof(C61A)=Sof(H61A)=Sof(C62A)=Sof(H62A)=
 Sof(C63A)=Sof(C64A)=Sof(H64A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=Sof(H66A)=
 Sof(C67A)=Sof(C68A)=Sof(C69A)=Sof(H69A)=Sof(C70A)=Sof(H70A)=Sof(C71A)=
 Sof(H71A)=Sof(C72A)=Sof(C73A)=Sof(H73A)=Sof(C74A)=Sof(H74A)=Sof(C75A)=
 Sof(H75A)=Sof(C76A)=Sof(C77A)=Sof(C78A)=1-FVAR(2)
 Sof(C59)=Sof(C60)=Sof(H60)=Sof(C61)=Sof(H61)=Sof(C62)=Sof(H62)=Sof(C63)=
 Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=Sof(C66)=Sof(H66)=Sof(C67)=Sof(C68)=
 Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(C73)=
 Sof(H73)=Sof(C74)=Sof(H74)=Sof(C75)=Sof(H75)=Sof(C76)=Sof(C77)=Sof(C78)=FVAR(2)
 Sof(P3A)=Sof(F13A)=Sof(F14A)=Sof(F15A)=Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(3)
 Sof(P3)=Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=Sof(F17)=Sof(F18)=FVAR(3)
 Sof(P1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(4)
 Sof(P1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(4)
 Fixed Sof: C89(0.25) H89(0.25) C90(0.25) H90(0.25) C91(0.25) C92(0.25)
 H92(0.25) C93(0.25) H93(0.25) C94(0.25) H94(0.25) C95(0.25) C96(0.25)
 C97(0.25) H97(0.25) C98(0.25) H98(0.25) C99(0.25) H99(0.25) C100(0.25)
 C101(0.25) H101(0.25) C102(0.25) H102(0.25) C103(0.25) H103(0.25) C104(0.25)
 C105(0.25) C106(0.25) H106(0.25) C107(0.25) C108(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C30(H30A,H30B), C51(H51A,H51B), C58(H58A,H58B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C7A(H7A), C11A(H11A), C10A(H10A),
 C8A(H8A), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17),
 C13A(H13A), C14A(H14A), C16A(H16A), C17A(H17A), C19(H19), C20(H20), C21(H21),
 C22(H22), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32), C34(H34),
  C35(H35), C36(H36), C36A(H36A), C37(H37), C37A(H37A), C39A(H39A), C43A(H43A),
 C42A(H42A), C40A(H40A), C40(H40), C39(H39), C43(H43), C42(H42), C44(H44),
 C44A(H44A), C45(H45), C45A(H45A), C47(H47), C48(H48), C49(H49), C50(H50),
 C53(H53), C54(H54), C56(H56), C57(H57), C60(H60), C60A(H60A), C61(H61),
 C61A(H61A), C62(H62), C62A(H62A), C64(H64), C64A(H64A), C65(H65), C65A(H65A),
 C66(H66), C66A(H66A), C69(H69), C69A(H69A), C70(H70), C70A(H70A), C71(H71),
 C71A(H71A), C73(H73), C73A(H73A), C74(H74), C74A(H74A), C75(H75), C75A(H75A),
 C79(H79), C80(H80), C81(H81), C84(H84), C85(H85), C86(H86), C89(H89), C90(H90),
  C92(H92), C93(H93), C94(H94), C97(H97), C98(H98), C99(H99), C101(H101),
 C102(H102), C103(H103), C106(H106)
6.c Idealised Me refined as rotating group:
 C110(H11B,H11C,H11D), C112(H11E,H11F,H11G), C114(H11H,H11I,H11J), C116(H11K,
 H11L,H11M)
;
_shelx_res_checksum              72942
_shelx_hkl_checksum              40161
_olex2_date_sample_data_collection 2018-04-23
_olex2_date_sample_submission    2018-04-18
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1273
_olex2_submission_special_instructions 'No special instructions were received'