Small Molecule Near-Infrared BODIPY Donors for Organic Tandem Solar Cells.
Li, Tian-Yi; Meyer, Toni; Ma, Zaifei; Benduhn, Johannes; Koerner, Christian; Zeika, Olaf; Vandewal, Koen; Leo, Karl; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b07887

data_4126428
_publ_section_title
;
 Small Molecule Near-Infrared BODIPY Donors for Organic Tandem Solar
 Cells.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b07887
_journal_year                    2017
_chemical_formula_moiety         'C28 H18 B F5 N2 O4'
_chemical_formula_sum            'C28 H18 B F5 N2 O4'
_chemical_formula_weight         552.25
_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
_audit_creation_date             2017-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                91.530(2)
_cell_angle_beta                 91.845(3)
_cell_angle_gamma                108.004(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4718(5)
_cell_length_b                   9.4932(3)
_cell_length_c                   13.4657(3)
_cell_measurement_reflns_used    16151
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.5720
_cell_measurement_theta_min      4.8970
_cell_volume                     1150.06(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2850
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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     22.00  47.00   0.50    3.00    --   54.00  78.00 171.94   50
  2  \w     36.00  65.00   0.50    3.00    --   66.00  76.00 143.34   58
  3  \w     43.00  82.00   0.50    3.00    --   74.00  77.00 102.27   78
  4  \w     99.00 125.00   0.50    3.00    --   70.00  76.00 171.41   52
  5  \w    132.00 163.00   0.50   12.00    --  111.00  61.00 120.00   62
  6  \w    150.00 178.00   0.50   12.00    --  111.00  77.00 120.00   56
  7  \w    145.00 177.00   0.50   12.00    --  111.00  61.00  30.00   64
  8  \w    152.00 178.00   0.50   12.00    --  111.00  77.00 -30.00   52
  9  \w    135.00 176.00   0.50   12.00    --  111.00  77.00-150.00   82
 10  \w    117.00 143.00   0.50    3.00    --   70.00  76.00 -47.17   52
 11  \w    107.00 134.00   0.50    3.00    --   66.00  76.00  21.79   54
 12  \w    122.00 167.00   0.50   12.00    --  111.00  61.00 -30.00   90
 13  \w    116.00 151.00   0.50   12.00    --  111.00  77.00-120.00   70
 14  \w    112.00 165.00   0.50   12.00    --  111.00  77.00-180.00  106
 15  \w    104.00 144.00   0.50    3.00    --   74.00  76.00 -93.74   80
 16  \w    119.00 173.00   0.50   12.00    --  111.00  77.00   0.00  108
 17  \w     85.00 110.00   0.50   12.00    --  111.00  61.00 120.00   50
 18  \w     83.00 143.00   0.50   12.00    --  111.00  61.00  90.00  120
 19  \w     86.00 126.00   0.50   12.00    --  111.00  61.00  30.00   80
 20  \w     85.00 111.00   0.50   12.00    --  111.00  61.00 -30.00   52
 21  \w     85.00 132.00   0.50   12.00    --  111.00  61.00   0.00   94
 22  \w     79.00 119.00   0.50    3.00    --   58.00  76.00 -44.89   80
 23  \w     80.00 105.00   0.50   12.00    --  111.00  77.00   0.00   50
 24  \w     80.00 135.00   0.50   12.00    --  111.00  77.00  30.00  110
 25  \w     81.00 139.00   0.50   12.00    --  111.00  77.00 120.00  116
 26  \w     80.00 174.00   0.50   12.00    --  111.00  77.00 150.00  188
 27  \w     84.00 174.00   0.50   12.00    --  111.00  61.00  60.00  180
 28  \w     84.00 122.00   0.50   12.00    --  111.00  61.00-120.00   76
 29  \w     85.00 162.00   0.50   12.00    --  111.00  61.00-150.00  154
 30  \w     83.00 143.00   0.50   12.00    --  111.00  61.00 -90.00  120
 31  \w     84.00 125.00   0.50   12.00    --  111.00  61.00-180.00   82
 32  \w     80.00 106.00   0.50   12.00    --  111.00  77.00-120.00   52
 33  \w     80.00 105.00   0.50   12.00    --  111.00  77.00-150.00   50
 34  \w     80.00 106.00   0.50   12.00    --  111.00  77.00-180.00   52
 35  \w     80.00 176.00   0.50   12.00    --  111.00  77.00 -90.00  192
 36  \w     80.00 106.00   0.50   12.00    --  111.00  77.00  60.00   52
 37  \w     80.00 176.00   0.50   12.00    --  111.00  77.00  90.00  192
 38  \w     80.00 178.00   0.50   12.00    --  111.00  77.00 -60.00  196
 39  \w     80.00 111.00   0.50   12.00    --  111.00  77.00 -30.00   62
 40  \w     47.00  80.00   0.50   12.00    --   78.00  77.00 -27.46   66
 41  \w     39.00  65.00   0.50    3.00    --   70.00  76.00 -47.17   52
 42  \w     43.00  68.00   0.50    3.00    --   74.00  76.00 -93.74   50
 43  \w     35.00  61.00   0.50    3.00    --   66.00  77.00-110.59   52
 44  \w     29.00  55.00   0.50    3.00    --   58.00  76.00 -44.89   52
 45  \w     22.00  47.00   0.50    3.00    --   54.00  78.00   6.62   50
 46  \w     35.00  61.00   0.50    3.00    --   66.00  76.00  21.79   52
 47  \w     39.00  65.00   0.50    3.00    --   70.00  75.00  57.93   52
 48  \w     39.00  65.00   0.50    3.00    --   70.00  77.00  81.77   52
 49  \w     18.00  43.00   0.50    3.00    --   50.00  81.00 128.77   50
 50  \w     39.00  65.00   0.50    3.00    --   70.00  76.00 171.41   52
 51  \w     13.00  39.00   0.50    3.00    --   46.00  82.00  69.99   52
 52  \w      1.00  26.00   0.50    3.00    --   38.00  93.00 -75.70   50
 53  \w    -45.00 -12.00   0.50    3.00    --  -38.50 -57.00  30.00   66
 54  \w    -44.00 -12.00   0.50    3.00    --  -38.50 -57.00 -90.00   64
 55  \w    -62.00  30.00   0.50    3.00    --  -38.50  57.00 -30.00  184
 56  \w     17.00  42.00   0.50    3.00    --   50.00  82.00 -96.34   50
 57  \w     44.00  75.00   0.50    3.00    --   74.00  75.00-168.35   62
 58  \w     42.00 142.00   0.50   12.00    --  111.00 -77.00-120.00  200
 59  \w     83.00 109.00   0.50   12.00    --  111.00 -94.00 -60.00   52
 60  \w     70.00 121.00   0.50   12.00    --  111.00-125.00-120.00  102
 61  \w     69.00 121.00   0.50   12.00    --  111.00-125.00 -90.00  104
 62  \w     64.00 119.00   0.50   12.00    --  111.00-125.00  60.00  110
 63  \w    117.00 142.00   0.50   12.00    --  111.00 -77.00  60.00   50
 64  \w     52.00  93.00   0.50   12.00    --  111.00 -94.00 150.00   82
 65  \w     44.00 121.00   0.50   12.00    --  111.00-125.00 150.00  154
 66  \w     38.00  78.00   0.50   12.00    --  111.00 -77.00  60.00   80
 67  \w     40.00  98.00   0.50   12.00    --  111.00 -94.00  60.00  116
 68  \w     34.00  59.00   0.50   12.00    --  111.00 -94.00 -60.00   50
 69  \w      1.00  80.00   0.50    3.00    --   42.75 -99.00  60.00  158
 70  \w     31.00  87.00   0.50    3.00    --   42.75-125.00 -90.00  112
 71  \w   -108.00 -49.00   0.50    3.00    --  -38.50 -57.00  30.00  118
 72  \w   -108.00 -49.00   0.50    3.00    --  -38.50 -57.00 -90.00  118
 73  \w   -109.00 -12.00   0.50    3.00    --  -38.50 -57.00-180.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0337731000
_diffrn_orient_matrix_UB_12      -0.0584290000
_diffrn_orient_matrix_UB_13      0.1050749000
_diffrn_orient_matrix_UB_21      0.0582595000
_diffrn_orient_matrix_UB_22      0.1598360000
_diffrn_orient_matrix_UB_23      0.0441444000
_diffrn_orient_matrix_UB_31      -0.1573730000
_diffrn_orient_matrix_UB_32      0.0140915000
_diffrn_orient_matrix_UB_33      -0.0115081000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23344
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.691
_diffrn_reflns_theta_min         3.286
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.152
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.0036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4781
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0675
_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^)+(0.1220P)^2^+0.8451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2043
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4681
_reflns_number_total             4781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07887_si_004.cif
_cod_data_source_block           iapp007
_cod_original_cell_volume        1150.07(8)
_cod_database_code               4126428
_chemical_oxdiff_formula         C28H18BF5N2O4
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.741(2) 0.259(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
F1B \\sim F2B \\sim F3B \\sim C2: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F3A) = Uanis(F1B)
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F3A)=Sof(F4A)=Sof(F5A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27)
5.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              97072
_shelx_hkl_checksum              41758
_shelx_shelxl_version_number     2014/7
_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 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.774