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_4129154
_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         '2(C44 H36 N4), 9(F6 P), 14(C2 H3 N)'
_chemical_formula_sum            'C116 H114 F54 N22 P9'
_chemical_formula_weight         3121.02
_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             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                95.924(3)
_cell_angle_beta                 107.021(2)
_cell_angle_gamma                101.439(2)
_cell_formula_units_Z            1
_cell_length_a                   11.1018(6)
_cell_length_b                   17.7461(9)
_cell_length_c                   18.3231(11)
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.671
_cell_measurement_theta_min      3.307
_cell_volume                     3332.8(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      100.02
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0261
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32541
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.698
_diffrn_reflns_theta_max         66.698
_diffrn_reflns_theta_min         2.560
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.284
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0830 before and 0.0395 after correction. The Ratio of minimum to maximum transmission is 0.8022. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             1585
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.533
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.273
_refine_diff_density_min         -1.642
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1026
_refine_ls_number_reflns         11636
_refine_ls_number_restraints     414
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0923
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1547P)^2^+11.2326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2588
_refine_ls_wR_factor_ref         0.2616
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10948
_reflns_number_total             11636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            7(4PF6).cif
_cod_data_source_block           cx1295
_cod_database_code               4129154
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.671
_shelx_estimated_absorpt_t_min   0.376
_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
 F16-F15 \\sim F16-F13 \\sim F16-F17 \\sim F16-F14 \\sim F15-F13 \\sim F15-F18
\\sim F15-F14 \\sim F13-F17
 \\sim F13-F18 \\sim F17-F18 \\sim F17-F14 \\sim F18-F14
 with sigma of 0.04
 P3-F16 \\sim P3-F15 \\sim P3-F13 \\sim P3-F17 \\sim P3-F18 \\sim P3-F14
 with sigma of 0.02
 F16A-F15A \\sim F16A-F13A \\sim F16A-F17A \\sim F16A-F14A \\sim F15A-F13A
\\sim F15A-F18A \\sim F15A-
 F14A \\sim F13A-F17A \\sim F13A-F18A \\sim F17A-F18A \\sim F17A-F14A \\sim
F18A-F14A
 with sigma of 0.04
 P3A-F16A \\sim P3A-F15A \\sim P3A-F13A \\sim P3A-F17A \\sim P3A-F18A \\sim
P3A-F14A
 with sigma of 0.02
3. Rigid bond restraints
 N11, N11A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 P3, F13, F14, F15, F16, F17, F18, P3A, F13A, F14A, F15A, F16A, F17A, F18A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N11 \\sim N11A: 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 P3A \\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
5. Others
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=
 Sof(H33A)=1-FVAR(1)
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=FVAR(1)
 Sof(N11A)=Sof(H57A)=Sof(H57B)=Sof(H57C)=1-FVAR(2)
 Sof(N11)=Sof(H58A)=Sof(H58B)=Sof(H58C)=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)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C23(H23A,H23B), C34(H34A,H34B)
6.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),
 C15(H15), C17(H17), C19(H19), C20(H20), C22(H22), C24(H24), C25(H25), C27(H27),
  C28(H28), 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)
6.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C), C52(H52A,H52B,
 H52C), C54(H54A,H54B,H54C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C58(H58A,
 H58B,H58C)
;
_shelx_res_checksum              62695
_shelx_hkl_checksum              97489
_olex2_date_sample_data_collection 2018-05-21
_olex2_date_sample_submission    2018-05-18
_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 cx1295
_olex2_submission_special_instructions 'No special instructions were received'