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_4133513
_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, 2(C14 H10), 4(F6 P), 4(C2 H3 N)'
_chemical_formula_sum            'C94 H80 F24 N8 P4'
_chemical_formula_weight         1901.54
_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             2018-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_cell_angle_alpha                79.7093(16)
_cell_angle_beta                 86.3983(16)
_cell_angle_gamma                64.3662(16)
_cell_formula_units_Z            1
_cell_length_a                   10.3102(7)
_cell_length_b                   11.1967(8)
_cell_length_c                   21.5627(15)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.087
_cell_measurement_theta_min      2.402
_cell_volume                     2207.8(3)
_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      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            44153
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         0.960
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0470 before and 0.0398 after correction. The Ratio of minimum to maximum transmission is 0.9371. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.498
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     951
_refine_ls_number_reflns         11742
_refine_ls_number_restraints     1022
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0884
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1455P)^2^+3.0243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2536
_refine_ls_wR_factor_ref         0.2790
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8771
_reflns_number_total             11742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b10526_si_006.cif
_cod_data_source_block           cx1264
_cod_database_code               4133513
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.894
_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
 C52-C43 \\sim C43-C44 \\sim C44-C45 \\sim C50-C45 \\sim C51-C50 \\sim C51-C52
 with sigma of 0.01
 C51-C43 \\sim C52-C45 \\sim C44-C50
 with sigma of 0.01
 C52-C44 \\sim C43-C45
 with sigma of 0.01
 C53A-C52A \\sim C54A-C53A \\sim C54A-C41A \\sim C42A-C41A \\sim C43A-C42A
\\sim C44A-C43A \\sim C45A-
 C44A \\sim C50A-C45A \\sim C51A-C50A \\sim C52A-C51A \\sim C52A-C43A \\sim
C46A-C45A \\sim C47A-C46A ~
 C48A-C47A \\sim C49A-C48A \\sim C50A-C49A
 with sigma of 0.01
 C42-C41 \\sim C54-C41 \\sim C54-C53 \\sim C53-C52 \\sim C52-C43 \\sim
C54A-C53A \\sim C54A-C41A ~
 C43A-C42A \\sim C44-C43 \\sim C52A-C43A \\sim C53A-C52A \\sim C52-C51 \\sim
C52A-C51A \\sim C51-C50 ~
 C51A-C50A \\sim C50-C45 \\sim C50-C49 \\sim C49-C48 \\sim C50A-C45A \\sim
C50A-C49A \\sim C49A-C48A ~
 C48A-C47A \\sim C47A-C46A \\sim C48-C47 \\sim C47-C46 \\sim C46A-C45A \\sim
C46-C45 \\sim C45A-C44A ~
 C45-C44 \\sim C44A-C43A \\sim C42A-C41A \\sim C43-C42
 with sigma of 0.01
3. Rigid bond restraints
 F1, F1A, F2, F2A, F3, F3A, F5, F5A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
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 C41A \\sim C42A
\\sim C43A \\sim C44A \\sim C45A \\sim C46A \\sim C47A \\sim C48A \\sim C49A
\\sim C50A \\sim C51A \\sim C52A \\sim C53A \\sim C54A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
F1 \\sim F1A \\sim F2 \\sim F2A \\sim F3 \\sim F3A \\sim F5 \\sim F5A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(1)
 Sof(F9)=Sof(F10)=Sof(F11)=Sof(F12)=FVAR(1)
 Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(C44A)=Sof(H44A)=
 Sof(C45A)=Sof(C46A)=Sof(H46A)=Sof(C47A)=Sof(H47A)=Sof(C48A)=Sof(H48A)=
 Sof(C49A)=Sof(H49A)=Sof(C50A)=Sof(C51A)=Sof(H51A)=Sof(C52A)=Sof(C53A)=
 Sof(H53A)=Sof(C54A)=Sof(H54A)=0.5*(1-FVAR(3))
 Sof(C41)=Sof(H41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(C44)=Sof(H44)=Sof(C45)=
 Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49)=
 Sof(C50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(C53)=Sof(H53)=Sof(C54)=Sof(H54)=0.5*
 FVAR(3)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F5A)=1-FVAR(3)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F5)=FVAR(3)
 Fixed Sof: C14(0.5) C15(0.5) H15(0.5) C16(0.5) H16(0.5) C17(0.5) C18(0.5)
 H18(0.5) C19(0.5) H19(0.5) C20(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5)
 C23(0.5) C24(0.5) H24(0.5) C25(0.5) H25(0.5) C31(0.5) H31(0.5) C32(0.5)
 H32(0.5) C33(0.5) C34(0.5) H34(0.5) C35(0.5) H35(0.5) C36(0.5) C37(0.5)
 H37(0.5) C38(0.5) H38(0.5) C39(0.5) H39(0.5) C40(0.5) H40(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C44(H44),
  C46(H46), C47(H47), C48(H48), C49(H49), C51(H51), C53(H53), C54(H54),
 C41A(H41A), C42A(H42A), C44A(H44A), C46A(H46A), C47A(H47A), C48A(H48A),
 C49A(H49A), C51A(H51A), C53A(H53A), C54A(H54A), C56(H56), C57(H57), C58(H58),
 C59(H59), C61(H61)
6.c Idealised Me refined as rotating group:
 C65(H65A,H65B,H65C), C63(H63A,H63B,H63C)
;
_shelx_res_checksum              94040
_shelx_hkl_checksum              89056
_olex2_date_sample_data_collection 2018-04-18
_olex2_date_sample_submission    2018-04-13
_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 cx1264
_olex2_submission_special_instructions 'No special instructions were received'