Combining Intra- and Intermolecular Charge Transfer with Polycationic Cyclophanes to Design 2D Tessellations.
Cetin, Muhammet Mustafa; Beldjoudi, Yassine; Roy, Indranil; Anamimoghadam, Ommid; Bae, Youn Jue; Young, Ryan M.; Krzyaniak, Matthew D.; Stern, Charlotte L.; Philp, Douglas; Alsubaie, Fehaid M.; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b07877

data_4129148
_publ_section_title
;
 Combining Intra- and Intermolecular Charge Transfer with Polycationic
 Cyclophanes to Design 2D Tessellations.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b07877
_journal_year                    2019
_chemical_formula_moiety         '7.5(C6 H4 S4), C66 H54 N6, 6(F6 P)'
_chemical_formula_sum            'C111 H84 F36 N6 P6 S30'
_chemical_formula_weight         3333.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-22 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 107.481(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1639(12)
_cell_length_b                   33.6907(18)
_cell_length_c                   23.3216(14)
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.75
_cell_measurement_theta_min      2.75
_cell_volume                     14362.1(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.04
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27780
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        37.370
_diffrn_reflns_theta_max         37.370
_diffrn_reflns_theta_min         2.380
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.609
_exptl_absorpt_correction_T_max  0.7483
_exptl_absorpt_correction_T_min  0.4987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1010 before and 0.0656 after correction. The Ratio of minimum to maximum transmission is 0.6664. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       plates
_exptl_crystal_F_000             6744
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1690
_refine_ls_number_reflns         7170
_refine_ls_number_restraints     452
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.1031
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2702
_refine_ls_wR_factor_ref         0.3071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4623
_reflns_number_total             7170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            4(6PF6)_TTF_FINALIZEDD.cif
_cod_data_source_block           yb022bisz1
_cod_database_code               4129148
_publcif_datablock.id            {5fb5b5c2-9d6c-4f91-85d8-11e9ac96b565}
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 S29-C90
 1.8 with sigma of 0.02
 S30-C90
 1.8 with sigma of 0.02
 S27-C89
 1.8 with sigma of 0.02
 C89-S26
 1.8 with sigma of 0.02
 S9-C95
 1.77 with sigma of 0.02
 C95-S7
 1.77 with sigma of 0.02
 C98-S8
 1.77 with sigma of 0.02
 C98-S6
 1.77 with sigma of 0.02
 C69-C70
 1.34 with sigma of 0.02
 C71-C70
 2.54 with sigma of 0.01
 C83-S23
 1.76 with sigma of 0.02
 C84-S25
 1.76 with sigma of 0.02
 C84-S28
 1.76 with sigma of 0.02
 C70-C69
 1.34 with sigma of 0.01
 C72-S20
 1.76 with sigma of 0.02
 S18-C71
 1.76 with sigma of 0.02
 C71-S17
 1.76 with sigma of 0.02
 C72-S19
 1.76 with sigma of 0.02
 C86-S25
 1.75 with sigma of 0.02
 S24-C82
 1.75 with sigma of 0.02
 S23-C81
 1.75 with sigma of 0.02
 C83-S24
 1.76 with sigma of 0.02
 S28-C85
 1.75 with sigma of 0.02
 C84-C83
 1.34 with sigma of 0.02
 C70-C69
 1.205 with sigma of 0.01
 C86-S25
 1.775 with sigma of 0.04
 S30-C92
 1.775 with sigma of 0.04
 S29-C91
 1.775 with sigma of 0.04
 C82-C81
 1.45 with sigma of 0.04
 C86-C85
 1.45 with sigma of 0.04
 S28-C85
 1.775 with sigma of 0.04
 C94-C93
 1.4 with sigma of 0.04
 C95-C98
 1.35 with sigma of 0.04
3. Restrained planarity
 S29, C90, S30, C92, C91
 with sigma of 0.1
 C89, S26, S27, C87, C88
 with sigma of 0.1
 S6, C98, S8, C96, C97
 with sigma of 0.1
 C93, S9, C95, S7, C94
 with sigma of 0.01
 C73, S19, C72, S20, C74
 with sigma of 0.01
4. Rigid bond restraints
 C102, C101
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C96, C97
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C93, C94
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C9, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C107, C108
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C8, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C65, C64
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C62, C63
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C67, C61
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C53, C56
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C54, C55
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C52
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C50, C47
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C49, C48
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C60, C59
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C27, C29
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C31, C32
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C30, C29
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C34, C33
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15, C23, C22, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C72, C71
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C97) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C95)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C41) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C84) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C93) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(S27) \\sim Ueq, Uanis(S26) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C53) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.2
Uanis(C54) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.2
Uanis(C96) \\sim Ueq, Uanis(C97) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C94) \\sim Ueq, Uanis(C93) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C109) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C110) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C107) \\sim Ueq, Uanis(C108) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C106) \\sim Ueq, Uanis(C105) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C73) \\sim Ueq, Uanis(C74) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C70) \\sim Ueq, Uanis(C69) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C16) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C111) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.01
Uanis(C90) \\sim Ueq, Uanis(C89) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C87) \\sim Ueq, Uanis(C88) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C83) \\sim Ueq, Uanis(C84) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C91) \\sim Ueq, Uanis(C92) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C103) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C58) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C68)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C48) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C60) \\sim Ueq, Uanis(C61) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C45) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C38)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C40) \\sim Ueq,
Uanis(C39) \\sim Ueq, Uanis(C37) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(C82) \\sim Ueq, Uanis(C81) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(N1) \\sim Ueq, Uanis(N5) \\sim Ueq: with sigma of 0.015 and sigma for
terminal atoms of 0.015
Uanis(C15) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
Uanis(C72) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C98) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C33) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C59) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
6. Rigid body (RIGU) restrains
 S28, C85, C86, S25
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
7.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C24(H24A,H24B), C35(H35A,H35B), C46(H46A,H46B), C57(H57A,
 H57B), C68(H68A,H68B)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C22(H22), C25(H25), C26(H26),
  C27(H27), C28(H28), C31(H31), C32(H32), C33(H33), C34(H34), C44(H44),
 C45(H45), C37(H37), C39(H39), C41(H41), C42(H42), C47(H47), C48(H48), C49(H49),
  C50(H50), C53(H53), C54(H54), C55(H55), C56(H56), C59(H59), C60(H60),
 C63(H63), C64(H64), C66(H66), C67(H67), C69(H69), C70(H70), C73(H73), C74(H74),
  C75(H75), C76(H76), C79(H79), C80(H80), C81(H81), C82(H82), C85(H85),
 C86(H86), C87(H87), C88(H88), C91(H91), C92(H92), C93(H93), C94(H94), C96(H96),
  C97(H97), C99(H99), C100(H100), C103(H103), C104(H104), C105(H105),
 C106(H106), C109(H109), C110(H110), C111(H111)
7.c Fitted hexagon refined as free rotating group:
 C38(C43,C44,C45,C36,C37)
;
_shelx_res_checksum              82764
_shelx_hkl_checksum              12857
_shelx_fab_checksum              54562
_olex2_submission_special_instructions 'No special instructions were received'