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_7237165
_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         'C29 H18 B F7 N2 O4'
_chemical_formula_sum            'C29 H18 B F7 N2 O4'
_chemical_formula_weight         602.26
_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             2016-11-08
_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                102.618(3)
_cell_angle_beta                 90.338(2)
_cell_angle_gamma                100.899(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6728(3)
_cell_length_b                   12.6770(6)
_cell_length_c                   13.41465(19)
_cell_measurement_reflns_used    6400
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      76.3250
_cell_measurement_theta_min      5.8700
_cell_volume                     1248.82(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      99.9(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 0.980
_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     -6.00  19.00   0.50    1.50    --   42.50 -26.00 -70.00   50
  2  \w      3.00  50.00   0.50    1.50    --   42.50 -99.00-150.00   94
  3  \w      9.00  80.00   0.50    1.50    --   42.50 -99.00 -90.00  142
  4  \w     37.00 139.00   0.50    6.00    --  111.00 -26.00 -70.00  204
  5  \w    103.00 156.00   0.50    6.00    --  111.00 -15.00  60.00  106
  6  \w    126.00 153.00   0.50    6.00    --  111.00  26.00  91.00   54
  7  \w     82.00 112.00   0.50    1.50    --   42.50  26.00  91.00   60
  8  \w    121.00 173.00   0.50    6.00    --  111.00 125.00  30.00  104
  9  \w     96.00 171.00   0.50    6.00    --  111.00 125.00 -60.00  150
 10  \w     50.00  77.00   0.50    6.00    --  111.00 -15.00  60.00   54
 11  \w     43.00 127.00   0.50    6.00    --  111.00 -30.00  30.00  168
 12  \w     72.00  99.00   0.50    6.00    --  111.00 -94.00  90.00   54
 13  \w     64.00 120.00   0.50    6.00    --  111.00-125.00  90.00  112
 14  \w     93.00 120.00   0.50    6.00    --  111.00-125.00  30.00   54
 15  \w     88.00 117.00   0.50    6.00    --  111.00-125.00 -30.00   58
 16  \w     76.00 116.00   0.50    6.00    --  111.00-125.00-120.00   80
 17  \w     91.00 117.00   0.50    6.00    --  111.00-125.00-180.00   52
 18  \w     55.00  82.00   0.50    6.00    --  111.00 -94.00 -60.00   54
 19  \w     49.00  76.00   0.50    6.00    --  111.00-125.00 -30.00   54
 20  \w     43.00  71.00   0.50    6.00    --  111.00-125.00  30.00   56
 21  \w     30.00 109.00   0.50    6.00    --  111.00 -94.00 -30.00  158
 22  \w     43.00  73.00   0.50    6.00    --  111.00-125.00-120.00   60
 23  \w     32.00  95.00   0.50    6.00    --  111.00 -94.00-120.00  126
 24  \w     46.00 130.00   0.50    6.00    --  111.00 -61.00 -30.00  168
 25  \w     62.00 109.00   0.50    6.00    --  111.00 -45.00 150.00   94
 26  \w     41.00 114.00   0.50    6.00    --  111.00 -61.00  60.00  146
 27  \w     33.00  98.00   0.50    1.50    --   42.50-125.00 150.00  130
 28  \w    -66.00  38.00   0.50    1.50    --  -38.50  26.00  91.00  208
 29  \w    -57.00 -27.00   0.50    1.50    --  -38.50  38.00-180.00   60
 30  \w     -6.00  23.00   0.50    1.50    --  -38.50  38.00-180.00   58
 31  \w   -113.00 -46.00   0.50    1.50    --  -38.50 -26.00 -70.00  134
 32  \w     34.00 154.00   0.50    6.00    --  111.00 -15.00-180.00  240
;
_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      -0.0130261000
_diffrn_orient_matrix_UB_12      0.1215811000
_diffrn_orient_matrix_UB_13      0.0404239000
_diffrn_orient_matrix_UB_21      0.2042998000
_diffrn_orient_matrix_UB_22      0.0326745000
_diffrn_orient_matrix_UB_23      0.0077102000
_diffrn_orient_matrix_UB_31      -0.0012660000
_diffrn_orient_matrix_UB_32      0.0164972000
_diffrn_orient_matrix_UB_33      -0.1104070000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.311
_diffrn_reflns_theta_min         3.380
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.691
_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 greenish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0756P)^2^+0.4296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4808
_reflns_number_total             5192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ta06261g2.cif
_cod_data_source_block           iapp001
_cod_database_code               7237165
_chemical_oxdiff_formula         'C58 H36 B2 F14 N4 O8 '
_chemical_oxdiff_usercomment     LTY-90B
_reflns_odcompleteness_completeness 100.00
_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:
 C21(H21), C14(H14), C8(H8), C15(H15), C5(H5), C12(H12), C25(H25), C28(H28),
 C11(H11), C27(H27), C18(H18), C24(H24)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              42898
_shelx_hkl_checksum              55960
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.587