Direct Observation of a Charge-Transfer State Preceding High-Yield Singlet Fission in Terrylenediimide Thin Films.
Margulies, Eric A.; Logsdon, Jenna L.; Miller, Claire E.; Ma, Lin; Simonoff, Ethan; Young, Ryan M.; Schatz, George C.; Wasielewski, Michael R.; Journal of the American Chemical Society 139 (2017) 663–671; doi:10.1021/jacs.6b07721

data_4125747
_publ_section_title
;
 Direct Observation of a Charge-Transfer State Preceding High-Yield
 Singlet Fission in Terrylenediimide Thin Films.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              663
_journal_page_last               671
_journal_paper_doi               10.1021/jacs.6b07721
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C74 H62 N2 O4'
_chemical_formula_sum            'C74 H62 N2 O4'
_chemical_formula_weight         1043.25
_chemical_name_systematic        hPhTDIc8
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.586(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   36.0857(14)
_cell_length_b                   4.8422(2)
_cell_length_c                   32.6994(12)
_cell_measurement_reflns_used    6336
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      3.12
_cell_volume                     5313.0(4)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.957
_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  0.0777
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            22288
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.300
_diffrn_reflns_theta_min         4.587
_diffrn_source                   microsource
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.7351
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1218 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.7993. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       needle
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0689
_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^)+(0.1199P)^2^+5.4016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3031
_reflns_number_total             4651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07721_si_003.cif
_cod_data_source_block           hphtdic8_x
_cod_database_code               4125747
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.630
_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. Others
 Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(H27a)=Sof(C28A)=Sof(H28A)=
 Sof(C29A)=Sof(H29A)=1-FVAR(1)
 Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(H27)=Sof(C28)=Sof(H28)=Sof(C29)=
 Sof(H29)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C30(H30a,H30b), C31(H31a,H31b), C32(H32a,H32b), C33(H33a,H33b), C34(H34a,
 H34b), C35(H35a,H35b), C36(H36a,H36b)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C9(H9), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C25(H25), C25A(H25A), C26(H26), C26A(H26A), C27(H27), C27(H27a),
 C28(H28), C28A(H28A), C29(H29), C29A(H29A)
3.c Idealised Me refined as rotating group:
 C37(H37a,H37b,H37c)
;
_shelx_res_checksum              43503
_shelx_hkl_checksum              20862
_olex2_submission_special_instructions 'No special instructions were received'