Intramolecular Energy and Electron Transfer within a Diazaperopyrenium-Based Cyclophane.
Gong, Xirui; Young, Ryan M.; Hartlieb, Karel J.; Miller, Claire; Wu, Yilei; Xiao, Hai; Li, Peng; Hafezi, Nema; Zhou, Jiawang; Ma, Lin; Cheng, Tao; Goddard, 3rd, William A; Farha, Omar K.; Hupp, Joseph T.; Wasielewski, Michael R.; Stoddart, J. Fraser; Journal of the American Chemical Society 139 (2017) 4107–4116; doi:10.1021/jacs.6b13223

data_4125888
_publ_section_title
;
 Intramolecular Energy and Electron Transfer within a
 Diazaperopyrenium-Based Cyclophane.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4107
_journal_page_last               4116
_journal_paper_doi               10.1021/jacs.6b13223
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety
'C56 H40 N4, 1.5(C16 H10), 4(F6 P), 4(C2 H3 N)'
_chemical_formula_sum            'C88 H67 F24 N8 P4'
_chemical_formula_weight         1816.37
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2014-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                92.310(2)
_cell_angle_beta                 106.077(2)
_cell_angle_gamma                102.044(2)
_cell_formula_units_Z            1
_cell_length_a                   10.7635(6)
_cell_length_b                   11.6514(6)
_cell_length_c                   17.8407(9)
_cell_measurement_reflns_used    5027
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.373
_cell_measurement_theta_min      2.591
_cell_volume                     2091.09(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.822
_diffrn_measured_fraction_theta_max 0.929
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.822
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11494
_diffrn_reflns_point_group_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.460
_diffrn_reflns_theta_min         2.592
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.760
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0772 before and 0.0342 after correction.
The Ratio of minimum to maximum transmission is 0.8581.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       rod
_exptl_crystal_F_000             927
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.076
_refine_diff_density_max         1.312
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.776
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     822
_refine_ls_number_reflns         6199
_refine_ls_number_restraints     1456
_refine_ls_restrained_S_all      1.753
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.1160
_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          0.3593
_refine_ls_wR_factor_ref         0.3886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4854
_reflns_number_total             6199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13223_si_002.cif
_cod_data_source_block           cx0170
_cod_original_cell_volume        2091.08(19)
_cod_database_code               4125888
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.878
_shelx_estimated_absorpt_t_min   0.612
_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
 F7-F12 \\sim F7-F11 \\sim F7-F10 \\sim F7-F9 \\sim F12-F11 \\sim F12-F8 \\sim
F12-F10 \\sim F11-F8 \\sim F11-
 F9 \\sim F8-F10 \\sim F8-F9 \\sim F10-F9 \\sim F7A-F12A \\sim F7A-F11A \\sim
F7A-F10A \\sim F7A-F9A \\sim F12A-
 F11A \\sim F12A-F8A \\sim F12A-F10A \\sim F11A-F8A \\sim F11A-F9A \\sim
F8A-F10A \\sim F8A-F9A \\sim F10A-
 F9A \\sim F8B-F7B \\sim F8B-F11B \\sim F8B-F9B \\sim F8B-F12B \\sim F7B-F11B
\\sim F7B-F10B \\sim F7B-F12B
 \\sim F11B-F10B \\sim F11B-F9B
 with sigma of 0.04
 P2-F7 \\sim P2-F12 \\sim P2-F11 \\sim P2-F8 \\sim P2-F10 \\sim P2-F9 \\sim
P2A-F7A \\sim P2A-F12A \\sim P2A-
 F11A \\sim P2A-F8A \\sim P2A-F10A \\sim P2A-F9A \\sim P2B-F8B \\sim P2B-F7B
\\sim P2B-F11B \\sim P2B-F10B
 \\sim P2B-F9B \\sim P2B-F12B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(P2B) = Uanis(P2) = Uanis(P2A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(P2)+Sof(F7)+Sof(F8)+Sof(F9)+Sof(F10)+Sof(F11)+Sof(F12)]+1*[Sof(P2A)+
 Sof(F7A)+Sof(F8A)+Sof(F9A)+Sof(F10A)+Sof(F11A)+Sof(F12A)]+1*[Sof(P2B)+Sof(F7B)+
 Sof(F8B)+Sof(F9B)+Sof(F10B)+Sof(F11B)+Sof(F12B)]=1 with esd of 0.00001
 Sof(P2)=Sof(F7)=Sof(F8)=Sof(F9)=Sof(F10)=Sof(F11)=Sof(F12)=FVAR(1)
 Sof(P2A)=Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=FVAR(2)
 Sof(P2B)=Sof(F7B)=Sof(F8B)=Sof(F9B)=Sof(F10B)=Sof(F11B)=Sof(F12B)=FVAR(3)
 Fixed Sof: H3(0.5) C4(0.5) H4(0.5) C5(0.5) H5(0.5) H6(0.5) H7(0.5) C8(0.5)
 H8(0.5) C9(0.5) H9(0.5) H10(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) H15(0.5)
 H16(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) H20(0.5) C41(0.25)
 H41(0.25) C42(0.25) H42(0.25) C43(0.25) C44(0.25) H44(0.25) C45(0.25)
 H45(0.25) C46(0.25) C47(0.25) H47(0.25) C48(0.25) H48(0.25) C49(0.25)
 H49(0.25) C50(0.25) C51(0.25) H51(0.25) C52(0.25) H52(0.25) C53(0.25)
 C54(0.25) H54(0.25) C55(0.25) C56(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C26(H26A,H26B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
  C19(H19), C20(H20), C21(H21), C28(H28), C29(H29), C31(H31), C32(H32),
 C41(H41), C42(H42), C44(H44), C45(H45), C47(H47), C48(H48), C49(H49), C51(H51),
  C52(H52), C54(H54), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
6.c Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C60(H60A,H60B,H60C)
;
_shelx_res_checksum              40402
_shelx_hkl_checksum              22880
_olex2_date_sample_data_collection 12/03/2014
_olex2_date_sample_submission    12/01/2014
_olex2_submission_original_sample_id 04-044-CF
_olex2_submission_special_instructions 'No special instructions were received'