Aza-BODIPY dyes with heterocyclic substituents and their derivatives bearing a cyanide co-ligand: NIR donor materials for vacuum-processed solar cells
Li, Tian-yi; Meyer, Toni; Meerheim, Rico; Höppner, Marco; Körner, Christian; Vandewal, Koen; Zeika, Olaf; Leo, Karl; Journal of Materials Chemistry A 5 (2017) 10696–; doi:10.1039/C7TA02133J

data_7236569
_publ_section_title
;
 Aza-BODIPY dyes with heterocyclic substituents and their derivatives
 bearing a cyanide co-ligand: NIR donor materials for vacuum-processed
 solar cells
;
_journal_issue                   21
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              10696
_journal_paper_doi               10.1039/C7TA02133J
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C34 H24 B F2 N5'
_chemical_formula_sum            'C34 H24 B F2 N5'
_chemical_formula_weight         551.39
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-24 deposited with the CCDC.
2017-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                85.313(4)
_cell_angle_beta                 73.628(3)
_cell_angle_gamma                65.884(3)
_cell_formula_units_Z            2
_cell_length_a                   10.9204(11)
_cell_length_b                   11.8225(12)
_cell_length_c                   12.8908(13)
_cell_measurement_reflns_used    7216
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.744
_cell_measurement_theta_min      2.426
_cell_volume                     1456.4(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker KAPPA APEX2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30684
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         1.648
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0709
_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^)+(0.1302P)^2^+0.0043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4368
_reflns_number_total             6779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ta02133j2.cif
_cod_data_source_block           lty-2_100k
_cod_database_code               7236569
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.985
_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. Restrained distances
 C16B-C11B \\sim C11A-C16A
 with sigma of 0.01
 C10B-C11B \\sim C11A-C10A
 with sigma of 0.01
 N4B-C16B \\sim N4A-C16A
 with sigma of 0.01
 N4B-C9 \\sim N4A-C9
 with sigma of 0.01
 C9-C10A \\sim C10B-C9
 with sigma of 0.01
 C15B-C16B \\sim C15A-C16A
 with sigma of 0.01
 C14B-C15B \\sim C15A-C14A
 with sigma of 0.01
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.01
 C12A-C11A \\sim C11B-C12B
 with sigma of 0.01
 C14A-C13A \\sim C14B-C13B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C13B) = Uanis(C13A)
Uanis(C14A) = Uanis(C14B)
Uanis(C12A) = Uanis(C12B)
Uanis(C15A) = Uanis(C15B)
Uanis(C11B) = Uanis(C11A)
Uanis(C16B) = Uanis(C16A)
Uanis(C10B) = Uanis(C10A)
Uanis(N4A) = Uanis(N4B)
Uanis(C17A) = Uanis(C17B)
4. Others
 Sof(N4B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=
 Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(C17B)=
 Sof(H17A)=Sof(H17B)=Sof(H17C)=1-FVAR(1)
 Sof(N4A)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C14A)=Sof(H14A)=
 Sof(C13A)=Sof(H13A)=Sof(C10A)=Sof(H10A)=Sof(C15A)=Sof(H15A)=Sof(C11A)=
 Sof(C12A)=Sof(H12A)=Sof(C16A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10B(H10B), C12B(H12B), C13B(H13B),
 C14B(H14B), C15B(H15B), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27),
 C29(H29), C30(H30), C31(H31), C32(H32), C14A(H14A), C13A(H13A), C10A(H10A),
 C15A(H15A), C12A(H12A)
5.b Idealised Me refined as rotating group:
 C17B(H17A,H17B,H17C), C34(H34A,H34B,H34C), C17A(H17D,H17E,H17F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_scan_rate                       21
_scan_width                      0.3