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_4129151
_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         'C66 H54 N6, 6(F6 P), C2 H3 N'
_chemical_formula_sum            'C68 H57 F36 N7 P6'
_chemical_formula_weight         1842.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.175(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.639(3)
_cell_length_b                   13.6292(13)
_cell_length_c                   40.821(4)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.145
_cell_measurement_theta_min      3.501
_cell_volume                     18666(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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1494
_diffrn_reflns_av_unetI/netI     0.1290
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            51397
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        65.794
_diffrn_reflns_theta_max         65.794
_diffrn_reflns_theta_min         1.085
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.082
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1246 before and 0.0860 after correction. The Ratio of minimum to maximum transmission is 0.7509. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       rod
_exptl_crystal_F_000             7424
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.771
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1265
_refine_ls_number_reflns         15901
_refine_ls_number_restraints     1664
_refine_ls_restrained_S_all      1.720
_refine_ls_R_factor_all          0.1940
_refine_ls_R_factor_gt           0.1795
_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          0.4517
_refine_ls_wR_factor_ref         0.4667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12561
_reflns_number_total             15901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            8(6PF6).cif
_cod_data_source_block           cx1348a_sq
_cod_original_cell_volume        18665(3)
_cod_database_code               4129151
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.631
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.605(3)
 0.395(3)
2. 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
3. Restrained distances
 P3-F16 = P3-F13 = P3-F17 = P3-F18 = P3-F14 = P3-F15
 1.6 with sigma of 0.02
 F29-F25 \\sim F29-F26 \\sim F29-F30 \\sim F29-F28 \\sim F25-F27 \\sim F26-F27
\\sim F26-F28
 with sigma of 0.02
 P5-F29 \\sim P5-F25 \\sim P5-F26 \\sim P5-F30 \\sim P5-F27 \\sim P5-F28
 with sigma of 0.01
 F35-F36 \\sim F35-F32 \\sim F35-F34 \\sim F35-F31 \\sim F33-F36 \\sim F33-F32
\\sim F33-F34 \\sim F33-F31
 \\sim F36-F32 \\sim F36-F31 \\sim F32-F34 \\sim F34-F31
 with sigma of 0.02
 P6-F35 \\sim P6-F33 \\sim P6-F36 \\sim P6-F32 \\sim P6-F34 \\sim P6-F31
 with sigma of 0.01
 F3-F1 \\sim F3-F6 \\sim F3-F2 \\sim F3-F4 \\sim F1-F6 \\sim F1-F5 \\sim F1-F4
\\sim F6-F5 \\sim F6-F2 \\sim F5-F2
 \\sim F5-F4 \\sim F2-F4
 with sigma of 0.02
 P1-F3 \\sim P1-F1 \\sim P1-F6 \\sim P1-F5 \\sim P1-F2 \\sim P1-F4
 with sigma of 0.01
 F38-F40 \\sim F38-F42 \\sim F38-F41 \\sim F38-F39 \\sim F40-F37 \\sim F40-F39
\\sim F37-F42 \\sim F37-F39
 \\sim F42-F41 \\sim F42-F39
 with sigma of 0.02
 P7-F38 \\sim P7-F40 \\sim P7-F37 \\sim P7-F42 \\sim P7-F41 \\sim P7-F39
 with sigma of 0.01
 N3-C28 \\sim N3-C28A
 with sigma of 0.02
 N3-C24 \\sim N3-C24A
 with sigma of 0.02
 C28-C27 \\sim C28A-C27A
 with sigma of 0.02
 C27-C26 \\sim C27A-C26
 with sigma of 0.02
 C26-C25 \\sim C26-C25A
 with sigma of 0.02
 C25-C24 \\sim C25A-C24A
 with sigma of 0.02
 C29-C30 \\sim C29-C30A
 with sigma of 0.02
 C29-C33 \\sim C29-C33A
 with sigma of 0.02
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C31-N4 \\sim C31A-N4
 with sigma of 0.02
 N4-C32 \\sim N4-C32A
 with sigma of 0.02
 C32-C33 \\sim C32A-C33A
 with sigma of 0.02
 N3-C27 \\sim N3-C27A
 with sigma of 0.04
 N3-C25 \\sim N3-C25A
 with sigma of 0.04
 C28-C26 \\sim C28A-C26
 with sigma of 0.04
 C26-C24 \\sim C26-C24A
 with sigma of 0.04
 C29-C31 \\sim C29-C31A
 with sigma of 0.04
 C29-C32 \\sim C29-C32A
 with sigma of 0.04
 C30-N4 \\sim C30A-N4
 with sigma of 0.04
 N4-C33 \\sim N4-C33A
 with sigma of 0.04
 F13-F15 \\sim F13-F16 \\sim F13-F17 \\sim F13-F18 \\sim F14-F15 \\sim F14-F16
\\sim F14-F17 \\sim F14-F18
 \\sim F15-F16 \\sim F15-F18 \\sim F16-F17 \\sim F17-F18
 with sigma of 0.02
 P3-F13 \\sim P3-F14 \\sim P3-F15 \\sim P3-F16 \\sim P3-F17 \\sim P3-F18
 with sigma of 0.01
 C17-C18 \\sim C17A-C18
 with sigma of 0.02
 C17-C16 \\sim C17A-C16A
 with sigma of 0.02
 C18-C19 \\sim C18-C19A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 C21-C16 \\sim C21A-C16A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C16-C15 \\sim C16A-C15A
 with sigma of 0.02
 C13-C14 \\sim C13-C14A
 with sigma of 0.02
 C13-C22 \\sim C13-C22A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C17-C21 \\sim C17A-C21A
 with sigma of 0.04
 C17-C15 \\sim C17A-C15A
 with sigma of 0.04
 C18-C20 \\sim C18-C20A
 with sigma of 0.04
 C18-C16 \\sim C18-C16A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
 C20-C16 \\sim C20A-C16A
 with sigma of 0.04
 C20-C22 \\sim C20A-C22A
 with sigma of 0.04
 C21-C13 \\sim C21A-C13
 with sigma of 0.04
 C21-C15 \\sim C21A-C15A
 with sigma of 0.04
 C16-C14 \\sim C16A-C14A
 with sigma of 0.04
 C16-C22 \\sim C16A-C22A
 with sigma of 0.04
 C13-C15 \\sim C13-C15A
 with sigma of 0.04
 C18-C17A \\sim C19A-C18 \\sim C20A-C19A \\sim C21A-C20A \\sim C21A-C16A \\sim
C17A-C16A \\sim C16A-
 C15A \\sim C15A-C14A \\sim C14A-C13 \\sim C22A-C13 \\sim C22A-C21A
 with sigma of 0.01
4. Restrained planarity
 C13, C14, C15, C21, C22
 with sigma of 0.1
 C16, C17, C18, C19, C20, C21
 with sigma of 0.01
 C13, C14A, C15A, C16A, C17A, C18, C19A, C20A, C21A, C22A
 with sigma of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C30A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
6. 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
7. Others
 Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=
 Sof(H28A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=
 Sof(C33A)=Sof(H33A)=1-FVAR(1)
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28)=
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(C22A)=Sof(H22A)=1-FVAR(2)
 Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(C22)=Sof(H22)=FVAR(2)
 Fixed Sof: P7(0.5) F37(0.5) F38(0.5) F39(0.5) F40(0.5) F41(0.5) F42(0.5)
 P3(0.5) F13(0.5) F14(0.5) F15(0.5) F16(0.5) F17(0.5) F18(0.5)
8.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C23(H23A,H23B), C34(H34A,H34B), C45(H45A,H45B),
 C56(H56A,H56B)
8.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C14A(H14A), C15(H15), C15A(H15A), C17(H17), C17A(H17A), C19(H19), C19A(H19A),
 C20(H20), C20A(H20A), C22(H22), C22A(H22A), C24(H24), C24A(H24A), C25(H25),
 C25A(H25A), C27(H27), C27A(H27A), C28(H28), C28A(H28A), C30(H30), C30A(H30A),
 C31(H31), C31A(H31A), C32(H32), C32A(H32A), C33(H33), C33A(H33A), C36(H36),
 C38(H38), C39(H39), C41(H41), C43(H43), C44(H44), C46(H46), C47(H47), C49(H49),
  C50(H50), C52(H52), C53(H53), C54(H54), C55(H55), C58(H58), C60(H60),
 C61(H61), C63(H63), C65(H65), C66(H66)
8.c Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              476
_shelx_hkl_checksum              58161
_shelx_fab_checksum              35466
_platon_squeeze_void_probe_radius 1.20
_olex2_date_sample_data_collection 2018-07-27
_olex2_date_sample_submission    2018-07-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone'
_olex2_submission_original_sample_id cx1348a
_olex2_submission_special_instructions 'No special instructions were received'