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_7236567
_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 H25 N5'
_chemical_formula_sum            'C34 H25 N5'
_chemical_formula_weight         503.59
_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             2015-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-03-24 deposited with the CCDC.
2017-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                102.045(3)
_cell_angle_beta                 108.397(3)
_cell_angle_gamma                99.521(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0354(4)
_cell_length_b                   11.8886(5)
_cell_length_c                   13.4146(6)
_cell_measurement_reflns_used    3146
_cell_measurement_temperature    200
_cell_measurement_theta_max      23.590
_cell_measurement_theta_min      2.413
_cell_volume                     1295.03(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_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  0.0527
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14241
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.192
_diffrn_reflns_theta_min         1.666
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9198
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            'metallic black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_recrystallization_method 'crystallized from dichloromethane'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0403P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0937
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2764
_reflns_number_total             4623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ta02133j2.cif
_cod_data_source_block           jh_lty_2_ligand_0m
_cod_original_cell_volume        1295.03(10)
_cod_database_code               7236567
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H3)=1-FVAR(1)
 Sof(H1)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C3(H3A), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13),
  C14(H14), C15(H15), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27),
 C29(H29), C30(H30), C31(H31), C32(H32)
3.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_olex2_date_sample_data_collection 2015-10-28
_olex2_date_sample_submission    2015-09-28
_olex2_exptl_crystal_mounting_method 'mounted on a glas fiber with epoxy'
_olex2_submission_original_sample_id LTY-2-ligand
_olex2_submission_special_instructions 'No special instructions were received'