H-Type-like Aggregation-Accelerated Singlet Fission Process in Dipyrrolonaphthyridinedione Thin Film: The Role of Charge Transfer/Excimer Mixed Intermediate State.
Wang, Long; Cai, Wanlin; Sun, Jing; Wu, Yuling; Zhang, Bin; Tian, Xiangbin; Guo, Shaoting; Liang, WanZhen; Fu, Hongbing; Yao, Jiannian; The journal of physical chemistry letters 12 (2021) 12276–12282; doi:10.1021/acs.jpclett.1c03265

data_8000563
_publ_section_title
;
 H-Type-like Aggregation-Accelerated Singlet Fission Process in
 Dipyrrolonaphthyridinedione Thin Film: The Role of Charge
 Transfer/Excimer Mixed Intermediate State.
;
_journal_issue                   51
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              12276
_journal_page_last               12282
_journal_paper_doi               10.1021/acs.jpclett.1c03265
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C14 H8 N2 O2'
_chemical_formula_sum            'C14 H8 N2 O2'
_chemical_formula_weight         236.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.592(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6191(2)
_cell_length_b                   3.79700(10)
_cell_length_c                   19.9030(5)
_cell_measurement_reflns_used    3574
_cell_measurement_temperature    170.00(11)
_cell_measurement_theta_max      71.7040
_cell_measurement_theta_min      4.4500
_cell_volume                     498.61(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      170.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -119.00 -59.00   1.00    0.20    --  -46.95-143.00-124.00   60
  2  \w   -119.00 -70.00   1.00    0.20    --  -46.95-127.00  45.00   49
  3  \w     26.00 105.00   1.00    0.20    --   46.95-143.00-124.00   79
  4  \w     18.00  96.00   1.00    0.20    --   46.95-127.00  45.00   78
  5  \w   -130.00 -26.00   1.00    0.50    --  -99.00 143.00 -68.00  104
  6  \w     65.00 169.00   1.00    0.50    --  103.25 143.00 -68.00  104
  7  \w   -118.00 -32.00   1.00    0.20    --  -46.95 -57.00  30.00   86
  8  \w   -119.00 -71.00   1.00    0.20    --  -46.95-125.00 150.00   48
  9  \w    -59.00  26.00   1.00    0.20    --  -46.95  38.00 120.00   85
 10  \w   -119.00 -71.00   1.00    0.20    --  -46.95-125.00-150.00   48
 11  \w   -118.00 -26.00   1.00    0.50    --  -99.00 127.00 121.00   92
 12  \w   -113.00 -24.00   1.00    0.50    --  -99.00  15.00 -90.00   89
 13  \w   -112.00 -27.00   1.00    0.50    --  -99.00  45.00 -60.00   85
 14  \w   -168.00 -27.00   1.00    0.50    --  -99.00   0.00 120.00  141
 15  \w   -168.00 -86.00   1.00    0.50    --  -99.00 -30.00 -60.00   82
 16  \w   -122.00 -26.00   1.00    0.50    --  -99.00  77.00 -30.00   96
 17  \w   -112.00 -27.00   1.00    0.50    --  -99.00  45.00 150.00   85
 18  \w   -115.00 -26.00   1.00    0.50    --  -99.00  61.00 150.00   89
 19  \w   -168.00 -81.00   1.00    0.50    --  -99.00 -94.00 150.00   87
 20  \w     31.00 120.00   1.00    0.50    --  103.25 -61.00 -60.00   89
 21  \w     28.00 116.00   1.00    0.50    --  103.25 -30.00   0.00   88
 22  \w   -118.00 -32.00   1.00    0.20    --  -46.95 -57.00-150.00   86
 23  \w   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00  30.00   95
 24  \w   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00 120.00   95
 25  \w   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00-180.00   95
 26  \w   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00 -60.00   95
 27  \w     32.00 118.00   1.00    0.20    --   46.95  57.00  30.00   86
 28  \w     24.00 119.00   1.00    0.20    --   46.95  77.00 120.00   95
 29  \w   -168.00 -86.00   1.00    0.50    --  -99.00 -45.00 150.00   82
 30  \w   -168.00 -86.00   1.00    0.50    --  -99.00 -30.00-120.00   82
 31  \w   -168.00 -82.00   1.00    0.50    --  -99.00 -61.00  60.00   86
 32  \w     87.00 169.00   1.00    0.50    --  103.25  61.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080983000
_diffrn_orient_matrix_UB_12      -0.0473168000
_diffrn_orient_matrix_UB_13      -0.0766150000
_diffrn_orient_matrix_UB_21      -0.0134632000
_diffrn_orient_matrix_UB_22      -0.4023563000
_diffrn_orient_matrix_UB_23      0.0085203000
_diffrn_orient_matrix_UB_31      -0.2329689000
_diffrn_orient_matrix_UB_32      0.0214320000
_diffrn_orient_matrix_UB_33      -0.0094116000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8690
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.928
_diffrn_reflns_theta_min         4.457
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0410P)^2^+0.2063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                926
_reflns_number_total             995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jz1c03265_si_002.cif
_cod_data_source_block           tx941
_cod_database_code               8000563
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6)
;
_shelx_res_checksum              5963
_shelx_hkl_checksum              27859
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.499
_oxdiff_exptl_absorpt_empirical_full_min 0.621