Energy and Electron Transfer Dynamics within a Series of Perylene Diimide/Cyclophane Systems.
Ryan, Seán T J; Young, Ryan M.; Henkelis, James J.; Hafezi, Nema; Vermeulen, Nicolaas A.; Hennig, Andreas; Dale, Edward J.; Wu, Yilei; Krzyaniak, Matthew D.; Fox, Athan; Nau, Werner M.; Wasielewski, Michael R.; Stoddart, J. Fraser; Scherman, Oren A.; Journal of the American Chemical Society 137 (2015) 15299–15307; doi:10.1021/jacs.5b10329

data_4129753
_publ_section_title
;
 Energy and Electron Transfer Dynamics within a Series of Perylene
 Diimide/Cyclophane Systems.
;
_journal_issue                   48
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15299
_journal_page_last               15307
_journal_paper_doi               10.1021/jacs.5b10329
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety
'C50 H56 N4 O10, C48 H40 N4, 6(F6 P), 10.5(C2 H3 N)'
_chemical_formula_sum            'C119 H127.5 F36 N18.5 O10 P6'
_chemical_formula_weight         2846.71
_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   mixed
_audit_creation_date             2015-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                71.672(2)
_cell_angle_beta                 87.991(2)
_cell_angle_gamma                64.714(2)
_cell_formula_units_Z            2
_cell_length_a                   18.7124(7)
_cell_length_b                   20.0030(8)
_cell_length_c                   20.6195(8)
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.832
_cell_measurement_theta_min      3.670
_cell_volume                     6580.0(5)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            79412
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.140
_diffrn_reflns_theta_min         2.589
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.770
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0656 before and 0.0539 after correction. The Ratio of minimum to maximum transmission is 0.8486. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             2930
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.471
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2073
_refine_ls_number_reflns         23493
_refine_ls_number_restraints     245
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0877
_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^)+(0.1301P)^2^+15.3705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2410
_refine_ls_wR_factor_ref         0.2475
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20690
_reflns_number_total             23493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10329_si_002.cif
_cod_data_source_block           final
_cod_original_formula_sum        'C119 H127.50 F36 N18.50 O10 P6'
_cod_database_code               4129753
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N5S, C9S, C10S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F25, F26, F27, F28, F29, F30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5, O6, O7A, O7B, C79, C80A, C80B, C81, C82, C83
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F25, F26, F27, F28, F29, F30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F31, F32, F33, F34, F35, F36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N5S \\sim C9S \\sim C10S: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
F25 \\sim F26 \\sim F27 \\sim F28 \\sim F29 \\sim F30: within 2A with sigma of
0.5 and sigma for terminal atoms of 1
O5 \\sim O6 \\sim O7A \\sim O7B \\sim C79 \\sim C80A \\sim C80B \\sim C81 \\sim
C82 \\sim C83: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
F25 \\sim F26 \\sim F27 \\sim F28 \\sim F29 \\sim F30: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
F31 \\sim F32 \\sim F33 \\sim F34 \\sim F35 \\sim F36: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
Uanis(F27) \\sim Ueq, Uanis(F25) \\sim Ueq, Uanis(F29) \\sim Ueq, Uanis(F26)
\\sim Ueq, Uanis(F30) \\sim Ueq, Uanis(F28) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(C83) \\sim Ueq, Uanis(O7B) \\sim Ueq, Uanis(O7A) \\sim Ueq, Uanis(C82)
\\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(C80A) \\sim Ueq,
Uanis(C80B) \\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(F27) \\sim Ueq, Uanis(F25) \\sim Ueq, Uanis(F26) \\sim Ueq, Uanis(F30)
\\sim Ueq, Uanis(F28) \\sim Ueq, Uanis(F29) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(F31) \\sim Ueq, Uanis(F32) \\sim Ueq, Uanis(F33) \\sim Ueq, Uanis(F35)
\\sim Ueq, Uanis(F36) \\sim Ueq, Uanis(F34) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(C84) = Uanis(C86)
Uanis(C80A) = Uanis(C80B)
Uanis(O7A) = Uanis(O7B)
4. Others
 Sof(O7A)=Sof(H82C)=Sof(H82D)=Sof(H83C)=Sof(H83D)=1-FVAR(1)
 Sof(O7B)=Sof(H82A)=Sof(H82B)=Sof(H83A)=Sof(H83B)=FVAR(1)
 Sof(H79C)=Sof(H79D)=Sof(C80A)=Sof(H80A)=Sof(H80B)=1-FVAR(2)
 Sof(H79A)=Sof(H79B)=Sof(C80B)=Sof(H80C)=Sof(H80D)=FVAR(2)
 Fixed Sof: N2S(0.5) C3S(0.5) C4S(0.5) H4SA(0.5) H4SB(0.5) H4SC(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C79(H79C,H79D), C79(H79A,H79B), C80A(H80A,H80B), C80B(H80C,H80D), C81(H81A,
 H81B), C82(H82C,H82D), C82(H82A,H82B), C83(H83C,H83D), C83(H83A,H83B)
5.b Idealised Me refined as rotating group:
 C18S(H18A,H18B,H18C), C14S(H14A,H14B,H14C), C8S(H8SA,H8SB,H8SC), C10S(H10A,
 H10B,H10C), C12S(H12A,H12B,H12C), C22S(H22A,H22B,H22C), C6S(H6SA,H6SB,H6SC),
 C20S(H20A,H20B,H20C), C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,H4SC)
;
_shelx_res_checksum              64293
_shelx_hkl_checksum              22207
_olex2_submission_original_sample_id 'ExBox PDI [2]Cat'
_olex2_submission_special_instructions 'No special instructions were received'