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_4126426
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H14 B F5 N2 O2'
_chemical_formula_sum            'C26 H14 B F5 N2 O2'
_chemical_formula_weight         492.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.00279(10)
_cell_length_b                   16.5993(2)
_cell_length_c                   24.7770(3)
_cell_measurement_reflns_used    7495
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.2360
_cell_measurement_theta_min      3.1970
_cell_volume                     2057.55(5)
_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 10.5700
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -61.00  34.00   0.50    1.00    --  -38.50  38.00-150.00  190
  2  \w    -94.00  -2.00   0.50    1.00    --  -38.50 125.00  90.00  184
  3  \w     20.00 115.00   0.50    1.00    --   42.50  38.00 -30.00  190
  4  \w     16.00  59.00   0.50    1.00    --   42.50  57.00  90.00   86
  5  \w     41.00 139.00   0.50    3.00    --  111.00 -61.00  90.00  196
  6  \w     87.00 178.00   0.50    3.00    --  111.00  45.00 120.00  182
  7  \w     30.00 109.00   0.50    3.00    --  111.00 -94.00 -90.00  158
  8  \w     30.00 109.00   0.50    3.00    --  111.00 -94.00 120.00  158
  9  \w     39.00 121.00   0.50    3.00    --  111.00-125.00 -90.00  164
 10  \w     31.00 156.00   0.50    3.00    --  111.00 -15.00 120.00  250
 11  \w     66.00 178.00   0.50    3.00    --  111.00  15.00-150.00  224
 12  \w     80.00 178.00   0.50    3.00    --  111.00  77.00-180.00  196
 13  \w     30.00 109.00   0.50    3.00    --  111.00 -94.00 -60.00  158
;
_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      -0.0283154000
_diffrn_orient_matrix_UB_12      0.0100408000
_diffrn_orient_matrix_UB_13      0.0615667000
_diffrn_orient_matrix_UB_21      -0.2978619000
_diffrn_orient_matrix_UB_22      0.0210627000
_diffrn_orient_matrix_UB_23      -0.0070744000
_diffrn_orient_matrix_UB_31      -0.0727708000
_diffrn_orient_matrix_UB_32      -0.0898115000
_diffrn_orient_matrix_UB_33      0.0052075000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.587
_diffrn_reflns_theta_min         3.205
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.134
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.805
_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            'metallic green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1687 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.5648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4150
_reflns_number_total             4301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07887_si_002.cif
_cod_data_source_block           iapp003
_cod_original_cell_volume        2057.56(6)
_cod_database_code               4126426
_chemical_oxdiff_formula         'C104 H56 B4 F20 N8 O8 '
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_shelx_res_checksum              74097
_shelx_hkl_checksum              87805
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.759