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_4126427
_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 O2'
_chemical_formula_sum            'C28 H18 B F5 N2 O2'
_chemical_formula_weight         520.25
_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             2016-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                110.447(3)
_cell_angle_beta                 95.912(2)
_cell_angle_gamma                101.347(2)
_cell_formula_units_Z            4
_cell_length_a                   10.3958(3)
_cell_length_b                   13.9619(4)
_cell_length_c                   17.5164(6)
_cell_measurement_reflns_used    13226
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.2020
_cell_measurement_theta_min      2.7320
_cell_volume                     2294.50(14)
_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      100.0(2)
_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 0.989
_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    -73.00  40.00   0.50    2.00    --  -38.50  19.00-150.00  226
  2  \w    -34.00  -7.00   0.50    2.00    --  -38.50 125.00-120.00   54
  3  \w    -66.00 -13.00   0.50    2.00    --  -38.50 125.00-180.00  106
  4  \w   -111.00 -17.00   0.50    2.00    --  -38.50 -38.00  30.00  188
  5  \w     24.00  91.00   0.50    2.00    --   42.50-125.00   0.00  134
  6  \w     39.00  98.00   0.50    8.00    --  111.00 -77.00 120.00  118
  7  \w     82.00 109.00   0.50    8.00    --  111.00 -94.00 120.00   54
  8  \w     83.00 115.00   0.50    8.00    --  111.00-125.00 150.00   64
  9  \w    110.00 135.00   0.50    8.00    --  111.00 -30.00  90.00   50
 10  \w     70.00 136.00   0.50    8.00    --  111.00 -61.00   0.00  132
 11  \w     86.00 119.00   0.50    8.00    --  111.00-125.00 -30.00   66
 12  \w     68.00  98.00   0.50    8.00    --  111.00 -94.00-120.00   60
 13  \w    111.00 137.00   0.50    8.00    --  111.00 -61.00-150.00   52
 14  \w     76.00 134.00   0.50    8.00    --  111.00 -30.00 -90.00  116
 15  \w     88.00 172.00   0.50    8.00    --  111.00  77.00  30.00  168
 16  \w    145.00 170.00   0.50    8.00    --  111.00  77.00  60.00   50
 17  \w    121.00 162.00   0.50    8.00    --  111.00 125.00 -60.00   82
 18  \w    101.00 150.00   0.50    8.00    --  111.00 125.00 -30.00   98
 19  \w     87.00 133.00   0.50    8.00    --  111.00  77.00  60.00   92
 20  \w     36.00  91.00   0.50    8.00    --  111.00 -30.00  90.00  110
 21  \w     42.00 109.00   0.50    8.00    --  111.00 -94.00  30.00  134
 22  \w     43.00 121.00   0.50    8.00    --  111.00-125.00  30.00  156
 23  \w     46.00  96.00   0.50    8.00    --  111.00 -77.00 -90.00  100
 24  \w     42.00  90.00   0.50    8.00    --  111.00 -61.00-150.00   96
 25  \w     52.00 175.00   0.50    8.00    --  111.00   0.00-180.00  246
 26  \w     46.00  84.00   0.50    2.00    --   42.50-125.00-180.00   76
 27  \w     39.00  66.00   0.50    8.00    --  111.00 -30.00 -90.00   54
 28  \w     37.00  88.00   0.50    8.00    --  111.00 -77.00 -60.00  102
 29  \w     40.00 120.00   0.50    8.00    --  111.00-125.00-120.00  160
 30  \w     41.00  66.00   0.50    8.00    --  111.00-125.00 150.00   50
;
_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      0.0815786000
_diffrn_orient_matrix_UB_12      -0.0828662000
_diffrn_orient_matrix_UB_13      -0.0279407000
_diffrn_orient_matrix_UB_21      0.1304346000
_diffrn_orient_matrix_UB_22      0.0873938000
_diffrn_orient_matrix_UB_23      0.0397893000
_diffrn_orient_matrix_UB_31      -0.0019744000
_diffrn_orient_matrix_UB_32      -0.0168854000
_diffrn_orient_matrix_UB_33      0.0822528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.583
_diffrn_reflns_theta_min         2.741
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.049
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.841
_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    1.506
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         9531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0723P)^2^+0.7354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8496
_reflns_number_total             9531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07887_si_003.cif
_cod_data_source_block           iapp002
_cod_original_cell_volume        2294.49(12)
_cod_database_code               4126427
_chemical_oxdiff_formula         'C112 H72 B4 F20 N8 O8 '
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C7A(H7A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A),
 C17A(H17A), C20A(H20A), C23A(H23A), C24A(H24A), C26A(H26A), C27A(H27A),
 C4B(H4B), C7B(H7B), C10B(H10B), C11B(H11B), C13B(H13B), C14B(H14B), C17B(H17B),
  C20B(H20B), C23B(H23B), C24B(H24B), C26B(H26B), C27B(H27B)
2.b Idealised Me refined as rotating group:
 C15A(H15D,H15E,H15F), C28A(H28D,H28E,H28F), C15B(H15A,H15B,H15C), C28B(H28A,
 H28B,H28C)
;
_shelx_res_checksum              24036
_shelx_hkl_checksum              83648
_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.854