Mechanical-Bond-Induced Exciplex Fluorescence in an Anthracene-Based Homo[2]catenane.
Garci, Amine; Beldjoudi, Yassine; Kodaimati, Mohamad S.; Hornick, Jessica E.; Nguyen, Minh T.; Cetin, M. Mustafa; Stern, Charlotte L.; Roy, Indranil; Weiss, Emily A.; Stoddart, J. Fraser; Journal of the American Chemical Society 142 (2020) 7956–7967; doi:10.1021/jacs.0c02128

data_4134735
_publ_section_title
;
 Mechanical-Bond-Induced Exciplex Fluorescence in an Anthracene-Based
 Homo[2]catenane.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7956
_journal_page_last               7967
_journal_paper_doi               10.1021/jacs.0c02128
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C64 H48 N4, 4(F6 P), 0.5(C2 H3 N)'
_chemical_formula_sum            'C65 H49.5 F24 N4.5 P4'
_chemical_formula_weight         1473.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           17
_space_group_name_Hall           'P 2c 2'
_space_group_name_H-M_alt        'P 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9331(7)
_cell_length_b                   14.1803(9)
_cell_length_c                   42.533(2)
_cell_measurement_reflns_used    7488
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.718
_cell_measurement_theta_min      3.704
_cell_volume                     7197.2(7)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2017)'
_computing_data_collection       'APEX2 V2017.3 (Bruker, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0898
_diffrn_reflns_av_unetI/netI     0.1050
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            28512
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        63.881
_diffrn_reflns_theta_max         63.881
_diffrn_reflns_theta_min         2.077
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.897
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             2988
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.022
_refine_diff_density_max         2.515
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.222
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.717
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     918
_refine_ls_number_reflns         11178
_refine_ls_number_restraints     1863
_refine_ls_restrained_S_all      1.920
_refine_ls_R_factor_all          0.2299
_refine_ls_R_factor_gt           0.1971
_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          0.4554
_refine_ls_wR_factor_ref         0.4836
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                7529
_reflns_number_total             11178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02128_si_003.cif
_cod_data_source_block           cx1475
_cod_depositor_comments
'Adding full bibliography for 4134731--4134735.cif.'
_cod_original_formula_sum        'C65 H49.50 F24 N4.50 P4'
_cod_database_code               4134735
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.465
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.49(13)
 0.51(13)
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
 P1-F2 \\sim P1-F6 \\sim P1-F1 \\sim P1-F5 \\sim P1-F4 \\sim P1-F3 \\sim P3-F18
\\sim P3-F14 \\sim P3-F13 \\sim P3-
 F16 \\sim P3-F15 \\sim P3-F17 \\sim P4-F21 \\sim P4-F21_$1 \\sim P4-F19 \\sim
P4-F19_$1 \\sim P4-F20 \\sim P4-
 F20_$1 \\sim P5-F22 \\sim P5-F23 \\sim P5-F24 \\sim P5-F25 \\sim P5-F26 \\sim
P5-F27
 with sigma of 0.02
 F21-F19 \\sim F21-F19_$1 \\sim F21-F20 \\sim F21-F20_$1 \\sim F21_$1-F19 \\sim
F21_$1-F19_$1 ~
 F21_$1-F20 \\sim F21_$1-F20_$1 \\sim F19-F19_$1 \\sim F19-F20_$1 \\sim
F19_$1-F20 \\sim F18-F14 ~
 F18-F13 \\sim F18-F15 \\sim F18-F17 \\sim F14-F16 \\sim F14-F15 \\sim F13-F15
\\sim F13-F17 \\sim F16-F15
 \\sim F16-F17 \\sim F22-F25 \\sim F22-F26 \\sim F22-F27 \\sim F23-F24 \\sim
F23-F25 \\sim F23-F26 \\sim F23-
 F27 \\sim F24-F25 \\sim F24-F27 \\sim F25-F26 \\sim F26-F27 \\sim F2-F6 \\sim
F2-F5 \\sim F2-F4 \\sim F2-F3 ~
 F6-F1 \\sim F6-F5 \\sim F1-F5 \\sim F1-F4 \\sim F1-F3 \\sim F5-F4 \\sim F4-F3
 with sigma of 0.02
 C63-C58 \\sim C63-C62 \\sim C62-C61 \\sim C61-C60 \\sim C60-C59 \\sim C59-C58
 with sigma of 0.01
 C63-C61 \\sim C62-C60 \\sim C61-C59 \\sim C60-C58 \\sim C59-C63 \\sim C58-C62
 with sigma of 0.02
 C59-C60 \\sim C58-C59 \\sim C60-C61 \\sim C61-C62 \\sim C62-C63 \\sim C58-C63
 with sigma of 0.01
 P1-F2 \\sim P4-F20 \\sim P4-F20_$1 \\sim P5-F22 \\sim P5-F23 \\sim P5-F24
\\sim P5-F25 \\sim P5-F26 \\sim P5-
 F27 \\sim P1-F6 \\sim P1-F1 \\sim P1-F5 \\sim P1-F4 \\sim P1-F3 \\sim P3-F18
\\sim P3-F14 \\sim P3-F13 \\sim P3-
 F16 \\sim P3-F15 \\sim P3-F17 \\sim P4-F21 \\sim P4-F21_$1 \\sim P4-F19 \\sim
P4-F19_$1
 with sigma of 0.02
 F19-F21 \\sim F14-F15 \\sim F13-F15 \\sim F13-F17 \\sim F15-F16 \\sim F16-F17
\\sim F22-F25 \\sim F22-F26
 \\sim F22-F27 \\sim F23-F24 \\sim F23-F25 \\sim F23-F26 \\sim F23-F27 \\sim
F24-F25 \\sim F24-F27 \\sim F25-
 F26 \\sim F26-F27 \\sim F2-F6 \\sim F2-F5 \\sim F2-F4 \\sim F2-F3 \\sim F1-F6
\\sim F5-F6 \\sim F1-F5 \\sim F1-F4
 \\sim F1-F3 \\sim F4-F5 \\sim F3-F4 \\sim F21-F19_$1 \\sim F20-F21 \\sim
F21-F20_$1 \\sim F19-F21_$1 ~
 F21_$1-F19_$1 \\sim F20-F21_$1 \\sim F21_$1-F20_$1 \\sim F19-F19_$1 \\sim
F19-F20_$1 \\sim F20-
 F19_$1 \\sim F14-F18 \\sim F13-F18 \\sim F15-F18 \\sim F17-F18 \\sim F14-F16
 with sigma of 0.02
 C61-C63 \\sim C60-C62 \\sim C59-C61 \\sim C58-C60 \\sim C59-C63 \\sim C58-C62
 with sigma of 0.02
 C62-C63 \\sim C58-C63 \\sim C61-C62 \\sim C60-C61 \\sim C58-C59 \\sim C59-C60
 with sigma of 0.01
 P1-F6 \\sim P3-F16 \\sim P3-F15 \\sim P3-F17 \\sim P4-F21 \\sim P4-F21_$1
\\sim P4-F19 \\sim P4-F19_$1 ~
 P4-F20 \\sim P4-F20_$1 \\sim P5-F22 \\sim P5-F23 \\sim P5-F24 \\sim P5-F25
\\sim P5-F26 \\sim P5-F27 \\sim P1-
 F1 \\sim P1-F5 \\sim P1-F4 \\sim P1-F3 \\sim P3-F18 \\sim P3-F14 \\sim P3-F13
\\sim P1-F2
 with sigma of 0.02
 F21_$1-F20_$1 \\sim F4-F5 \\sim F3-F4 \\sim F19-F19_$1 \\sim F19-F20_$1 \\sim
F20-F19_$1 \\sim F14-
 F18 \\sim F13-F18 \\sim F15-F18 \\sim F17-F18 \\sim F14-F16 \\sim F14-F15
\\sim F13-F15 \\sim F13-F17 ~
 F15-F16 \\sim F16-F17 \\sim F22-F25 \\sim F22-F26 \\sim F22-F27 \\sim F23-F24
\\sim F23-F25 \\sim F23-F26
 \\sim F23-F27 \\sim F24-F25 \\sim F24-F27 \\sim F25-F26 \\sim F26-F27 \\sim
F2-F6 \\sim F2-F5 \\sim F2-F4 \\sim F2-
 F3 \\sim F1-F6 \\sim F5-F6 \\sim F1-F5 \\sim F1-F4 \\sim F1-F3 \\sim F19-F21
\\sim F21-F19_$1 \\sim F20-F21 ~
 F21-F20_$1 \\sim F19-F21_$1 \\sim F21_$1-F19_$1 \\sim F20-F21_$1
 with sigma of 0.02
 C58-C59 \\sim C59-C60 \\sim C60-C61 \\sim C61-C62 \\sim C58-C63 \\sim C62-C63
 with sigma of 0.01
 P1-F1 \\sim P1-F5 \\sim P1-F4 \\sim P1-F3 \\sim P3-F18 \\sim P3-F14 \\sim
P3-F13 \\sim P3-F16 \\sim P3-F15 ~
 P3-F17 \\sim P4-F21 \\sim P4-F21_$1 \\sim P4-F19 \\sim P4-F19_$1 \\sim P4-F20
\\sim P4-F20_$1 \\sim P5-F22
 \\sim P5-F23 \\sim P5-F24 \\sim P5-F25 \\sim P5-F26 \\sim P5-F27 \\sim P1-F6
\\sim P1-F2
 with sigma of 0.02
 F13-F15 \\sim F5-F6 \\sim F1-F5 \\sim F1-F4 \\sim F1-F3 \\sim F4-F5 \\sim
F3-F4 \\sim F13-F17 \\sim F15-F16 ~
 F16-F17 \\sim F22-F25 \\sim F22-F26 \\sim F22-F27 \\sim F23-F24 \\sim F23-F25
\\sim F23-F26 \\sim F23-F27
 \\sim F24-F25 \\sim F24-F27 \\sim F25-F26 \\sim F26-F27 \\sim F2-F6 \\sim
F2-F5 \\sim F2-F4 \\sim F2-F3 \\sim F1-
 F6 \\sim F19-F21 \\sim F21-F19_$1 \\sim F20-F21 \\sim F21-F20_$1 \\sim
F19-F21_$1 \\sim F21_$1-F19_$1
 \\sim F20-F21_$1 \\sim F21_$1-F20_$1 \\sim F14-F15 \\sim F19-F19_$1 \\sim
F19-F20_$1 \\sim F20-F19_$1
 \\sim F14-F18 \\sim F13-F18 \\sim F15-F18 \\sim F17-F18 \\sim F14-F16
 with sigma of 0.02
 C60-C62 \\sim C58-C60 \\sim C59-C63 \\sim C58-C62 \\sim C59-C61 \\sim C61-C63
 with sigma of 0.02
 C58-C63 \\sim C62-C63 \\sim C61-C62 \\sim C60-C61 \\sim C59-C60 \\sim C58-C59
 with sigma of 0.01
 P1-F1 \\sim P5-F22 \\sim P5-F23 \\sim P5-F24 \\sim P5-F25 \\sim P5-F26 \\sim
P5-F27 \\sim P1-F5 \\sim P1-F4 ~
 P1-F3 \\sim P3-F18 \\sim P3-F14 \\sim P3-F13 \\sim P3-F16 \\sim P3-F15 \\sim
P3-F17 \\sim P4-F21 \\sim P4-
 F21_$1 \\sim P4-F19 \\sim P4-F19_$1 \\sim P4-F20 \\sim P4-F20_$1 \\sim P1-F6
\\sim P1-F2
 with sigma of 0.02
 F5-F6 \\sim F1-F5 \\sim F1-F4 \\sim F1-F3 \\sim F4-F5 \\sim F3-F4 \\sim
F23-F27 \\sim F24-F25 \\sim F24-F27 ~
 F25-F26 \\sim F26-F27 \\sim F2-F6 \\sim F2-F5 \\sim F2-F4 \\sim F2-F3 \\sim
F1-F6 \\sim F19-F21 \\sim F21-
 F19_$1 \\sim F20-F21 \\sim F21-F20_$1 \\sim F19-F21_$1 \\sim F14-F15 \\sim
F13-F15 \\sim F13-F17 \\sim F15-
 F16 \\sim F16-F17 \\sim F22-F25 \\sim F22-F26 \\sim F22-F27 \\sim F23-F24
\\sim F23-F25 \\sim F23-F26 ~
 F21_$1-F19_$1 \\sim F20-F21_$1 \\sim F21_$1-F20_$1 \\sim F19-F19_$1 \\sim
F19-F20_$1 \\sim F20-
 F19_$1 \\sim F14-F18 \\sim F13-F18 \\sim F15-F18 \\sim F17-F18 \\sim F14-F16
 with sigma of 0.02
 C58-C60 \\sim C58-C62 \\sim C61-C63 \\sim C59-C63 \\sim C60-C62 \\sim C59-C61
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Others
 Fixed Sof: P3(0.5) F13(0.5) F14(0.5) F15(0.5) F16(0.5) F17(0.5) F18(0.5)
 H66A(0.5) H66B(0.5) H66C(0.5) P4(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C32(H32A,H32B), C57(H57A,H57B), C64(H64A,H64B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C12(H12), C14(H14),
 C15(H15), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27),
  C28(H28), C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37),
 C39(H39), C41(H41), C43(H43), C44(H44), C46(H46), C48(H48), C50(H50), C51(H51),
  C53(H53), C54(H54), C55(H55), C56(H56), C59(H59), C60(H60), C62(H62), C63(H63)
6.c Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C)
;
_shelx_res_checksum              54109
_shelx_hkl_checksum              55464
_shelx_fab_checksum              38933
_olex2_date_sample_data_collection 2019-01-07
_olex2_date_sample_submission    2019-01-02
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder'
_olex2_submission_original_sample_id cx1475
_olex2_submission_special_instructions 'No special instructions were received'