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_7236566
_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         'C27 H20 B F N6, C H4 N'
_chemical_formula_sum            'C28 H24 B F N7'
_chemical_formula_weight         488.35
_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             2015-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-03-24 deposited with the CCDC.
2017-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                89.038(2)
_cell_angle_beta                 73.997(2)
_cell_angle_gamma                87.037(2)
_cell_formula_units_Z            2
_cell_length_a                   7.5171(4)
_cell_length_b                   12.3224(6)
_cell_length_c                   13.2336(6)
_cell_measurement_reflns_used    7060
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.053
_cell_measurement_theta_min      2.300
_cell_volume                     1176.73(10)
_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      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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0569
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_min         1.601
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             510
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and hexane by slow evaporation'
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0646
_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^)+(0.0934P)^2^+0.5914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3762
_reflns_number_total             5685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ta02133j2.cif
_cod_data_source_block           jh_lty1_cn
_cod_database_code               7236566
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C19(H19), C16(H16), C5(H5), C18(H18), C10(H10),
 C23(H23), C17(H17), C11(H11), C12(H12), C25(H25), C24(H24)
2.c X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C13(H13A,H13B,H13C)
;
_olex2_date_sample_data_collection 2015-10-08
_olex2_date_sample_submission    2015-10-07
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre with two-component glue'
_olex2_submission_original_sample_id LTY1-CN
_olex2_submission_special_instructions 'No special instructions were received'