Boron dipyrromethene (BODIPY) with meso-perfluorinated alkyl substituents as near infrared donors in organic solar cells
Li, Tian-yi; Benduhn, Johannes; Li, Yue; Jaiser, Frank; Spoltore, Donato; Zeika, Olaf; Ma, Zaifei; Neher, Dieter; Vandewal, Koen; Leo, Karl; Journal of Materials Chemistry A 6 (2018) 18583–; doi:10.1039/C8TA06261G

data_7237166
_publ_section_title
;
 Boron dipyrromethene (BODIPY) with meso-perfluorinated alkyl substituents
 as near infrared donors in organic solar cells
;
_journal_issue                   38
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              18583
_journal_paper_doi               10.1039/C8TA06261G
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C30 H18 B F9 N2 O4'
_chemical_formula_sum            'C30 H18 B F9 N2 O4'
_chemical_formula_weight         652.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2018-02-14 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                93.918(2)
_cell_angle_beta                 105.682(3)
_cell_angle_gamma                97.023(3)
_cell_formula_units_Z            4
_cell_length_a                   11.7774(4)
_cell_length_b                   15.2002(4)
_cell_length_c                   17.0421(4)
_cell_measurement_reflns_used    14865
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      76.3620
_cell_measurement_theta_min      3.7830
_cell_volume                     2898.80(15)
_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(3)
_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 0.986
_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   -125.00  48.00   0.50    1.50    --  -38.50   0.00  60.00  346
  2  \w    -61.00  34.00   0.50    1.50    --  -38.50  38.00 -60.00  190
  3  \w     23.00  98.00   0.50    1.50    --   42.75-125.00-150.00  150
  4  \w     23.00  98.00   0.50    1.50    --   42.75-125.00 -30.00  150
  5  \w      1.00  83.00   0.50    1.50    --   42.75 -99.00  60.00  164
  6  \w     87.00 178.00   0.50    6.00    --  111.00  30.00   0.00  182
  7  \w     36.00 135.00   0.50    6.00    --  111.00 -30.00   0.00  198
  8  \w     30.00 109.00   0.50    6.00    --  111.00 -94.00   0.00  158
  9  \w     41.00 139.00   0.50    6.00    --  111.00 -61.00   0.00  196
 10  \w     39.00 121.00   0.50    6.00    --  111.00-125.00 120.00  164
 11  \w     39.00 121.00   0.50    6.00    --  111.00-125.00 -30.00  164
 12  \w     39.00 121.00   0.50    6.00    --  111.00-125.00-150.00  164
 13  \w     87.00 178.00   0.50    6.00    --  111.00  45.00  30.00  182
 14  \w     36.00 135.00   0.50    6.00    --  111.00 -30.00  90.00  198
 15  \w     37.00 142.00   0.50    6.00    --  111.00 -77.00 150.00  210
 16  \w     83.00 178.00   0.50    6.00    --  111.00  61.00-120.00  190
 17  \w    133.00 178.00   0.50    6.00    --  111.00 125.00-120.00   90
 18  \w     52.00 130.00   0.50    6.00    --  111.00 -30.00-180.00  156
 19  \w     56.00  89.00   0.50    6.00    --  111.00 -45.00 120.00   66
 20  \w     90.00 133.00   0.50    6.00    --  111.00 -45.00 120.00   86
 21  \w     39.00  68.00   0.50    6.00    --  111.00   0.00-180.00   58
 22  \w     75.00 111.00   0.50    6.00    --  111.00   0.00-180.00   72
 23  \w    112.00 164.00   0.50    6.00    --  111.00   0.00-180.00  104
 24  \w     40.00 100.00   0.50    6.00    --  111.00 -77.00 -60.00  120
 25  \w     67.00  94.00   0.50    6.00    --  111.00 -77.00   0.00   54
 26  \w    117.00 142.00   0.50    6.00    --  111.00 -77.00   0.00   50
 27  \w     77.00 104.00   0.50    6.00    --  111.00 -94.00-180.00   54
;
_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      -0.0554978000
_diffrn_orient_matrix_UB_12      -0.0340782000
_diffrn_orient_matrix_UB_13      -0.0912900000
_diffrn_orient_matrix_UB_21      -0.0359654000
_diffrn_orient_matrix_UB_22      0.0924143000
_diffrn_orient_matrix_UB_23      -0.0172110000
_diffrn_orient_matrix_UB_31      0.1203757000
_diffrn_orient_matrix_UB_32      0.0290684000
_diffrn_orient_matrix_UB_33      -0.0169123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36690
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.801
_diffrn_reflns_theta_min         2.708
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.214
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.891
_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    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     833
_refine_ls_number_reflns         12061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0752P)^2^+0.1931P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9714
_reflns_number_total             12061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ta06261g2.cif
_cod_data_source_block           iapp004
_cod_original_cell_volume        2898.81(16)
_cod_database_code               7237166
_chemical_oxdiff_formula         'C60 H36 B2 F18 N4 O8 '
_reflns_odcompleteness_completeness 99.97
_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:
 C6A(H6A), C9A(H9A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C19A(H19A), C22A(H22A), C25A(H25A), C26A(H26A), C28A(H28A), C29A(H29A),
 C6B(H6B), C9B(H9B), C12B(H12B), C13B(H13B), C15B(H15B), C16B(H16B), C19B(H19B),
  C22B(H22B), C25B(H25B), C26B(H26B), C28B(H28B), C29B(H29B)
2.b Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C30A(H30A,H30B,H30C), C17B(H17D,H17E,H17F), C30B(H30D,
 H30E,H30F)
;
_shelx_res_checksum              32539
_shelx_hkl_checksum              50663
_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 1.580
_oxdiff_exptl_absorpt_empirical_full_min 0.854