(Oligo-)Thiophene Functionalized Tetraazaperopyrenes: Donor-Acceptor Dyes and Ambipolar Organic Semiconductors.
Hahn, Lena; Hermannsdorfer, André; Günther, Benjamin; Wesp, Tobias; Bühler, Bastian; Zschieschang, Ute; Wadepohl, Hubert; Klauk, Hagen; Gade, Lutz H.; The Journal of organic chemistry 82 (2017) 12492–12502; doi:10.1021/acs.joc.7b02286

data_4033168
_publ_section_title
;
 (Oligo-)Thiophene Functionalized Tetraazaperopyrenes: Donor-Acceptor Dyes
 and Ambipolar Organic Semiconductors.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12492
_journal_page_last               12502
_journal_paper_doi               10.1021/acs.joc.7b02286
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C47.33 H16 Br8 F14 N4 S4'
_chemical_formula_weight         1674.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ah3
_audit_creation_date             2017-07-21
_audit_creation_method
;
Olex2 1.2
(compiled Mar 28 2017 19:34:44 for OlexSys, GUI svn.r5337)
;
_audit_update_record
'21.07.2017 17:00:33 CEST UTC+02:00  encif 1.71'
_cell_angle_alpha                90
_cell_angle_beta                 110.8723(13)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   15.36041(17)
_cell_length_b                   25.7224(2)
_cell_length_c                   20.8946(2)
_cell_measurement_reflns_used    60534
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      26.3020
_cell_measurement_theta_min      2.6140
_cell_volume                     7713.84(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-17); encifer 1.5.2 (CCDC, 2016)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    -46.00  52.00   0.50   12.50    --   26.27 -38.00  60.00  196
  2  \w    -46.00  52.00   0.50   12.50    --   26.27 -38.00 150.00  196
  3  \w      5.00  95.00   0.50   12.50    --   26.27  57.00 -30.00  180
  4  \w     13.00  98.00   0.50   12.50    --   26.27-147.00 -20.00  170
  5  \w      1.00  83.00   0.50   12.50    --   26.27-124.00 144.00  164
  6  \w      5.00  95.00   0.50   12.50    --   26.27  57.00  60.00  180
  7  \w     -4.00  96.00   0.50   12.50    --   26.27  77.00-150.00  200
  8  \w    -43.00  47.00   0.50   12.50    --   26.27 -57.00 -90.00  180
  9  \w    -43.00  47.00   0.50   12.50    --   26.27 -57.00   0.00  180
 10  \w      1.00  99.00   0.50   12.50    --   26.27  38.00-180.00  196
 11  \w     -4.00  96.00   0.50   12.50    --   26.27  77.00  90.00  200
 12  \w    -20.00  68.00   0.50   12.50    --   26.27 -99.00 -30.00  176
 13  \w      5.00  95.00   0.50   12.50    --   26.27  57.00-180.00  180
 14  \w      1.00  99.00   0.50   12.50    --   26.27  38.00 -60.00  196
 15  \w     -5.00  24.00   0.50   12.50    --   26.27  80.00  66.77   58
 16  \w    -20.00  68.00   0.50   12.50    --   26.27 -99.00-180.00  176
 17  \w      1.00  99.00   0.50   12.50    --   26.27  38.00 120.00  196
 18  \f      0.00 120.00   0.50   12.50  26.27  26.27 -40.00    --   240
 19  \f      0.00 120.00   0.50   12.50  26.27  26.27  40.00    --   240
 20  \w     -4.00  96.00   0.50   12.50    --   26.27  77.00 -30.00  200
 21  \f      0.00 120.00   0.50   12.50  26.27  26.27  60.00    --   240
 22  \f    120.00 240.00   0.50   12.50  26.27  26.27 -40.00    --   240
 23  \f    120.00 240.00   0.50   12.50  26.27  26.27  40.00    --   240
 24  \f    120.00 240.00   0.50   12.50  26.27  26.27 -60.00    --   240
 25  \f    120.00 240.00   0.50   12.50  26.27  26.27  60.00    --   240
 26  \f    240.00 360.00   0.50   12.50  26.27  26.27 -40.00    --   240
 27  \f    240.00 360.00   0.50   12.50  26.27  26.27  40.00    --   240
 28  \f    240.00 360.00   0.50   12.50  26.27  26.27 -60.00    --   240
 29  \f      0.00 120.00   0.50   12.50  26.27  26.27 -60.00    --   240
 30  \w     -4.00  21.00   0.50   12.50    --   26.27  77.00-180.00   50
 31  \f    240.00 360.00   0.50   12.50  26.27  26.27  60.00    --   240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0049005000
_diffrn_orient_matrix_UB_12      0.0274288000
_diffrn_orient_matrix_UB_13      -0.0004500000
_diffrn_orient_matrix_UB_21      0.0380517000
_diffrn_orient_matrix_UB_22      0.0016852000
_diffrn_orient_matrix_UB_23      0.0315327000
_diffrn_orient_matrix_UB_31      0.0311446000
_diffrn_orient_matrix_UB_32      0.0022686000
_diffrn_orient_matrix_UB_33      -0.0180510000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            413499
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.582
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.493
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.290
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model (Busing & Levy, 1957).
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.162
_exptl_crystal_description       needle
_exptl_crystal_F_000             4788
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.028
_refine_diff_density_max         2.437
_refine_diff_density_min         -1.008
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1047
_refine_ls_number_reflns         15801
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+30.3207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13021
_reflns_number_total             15801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02286_si_002.cif
_cod_data_source_block           ga_ah3
_cod_depositor_comments
'Adding full bibliography for 4033164--4033168.cif.'
_cod_original_cell_volume        7713.83(16)
_cod_database_code               4033168
_audit_block_refno               2556
_audit_block_usercomment         'AH-029 needle orange'
_shelx_estimated_absorpt_t_max   0.860
_shelx_estimated_absorpt_t_min   0.287
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_shelxl_version_number           2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C105-C104 \\sim C102-C101
 with sigma of 0.02
 C104-C103 \\sim C103-C102
 with sigma of 0.02
 C101-C103 \\sim C105-C103
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C101, C102, C103, C104, C105
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C102(H10D,H10E), C103(H10F,H10G), C104(H10H,H10I)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C12(H12), C18(H18), C32(H32), C36(H36), C40(H40), C44(H44),
 C53(H53), C59(H59), C82(H82), C86(H86)
4.c Idealised Me refined as rotating group:
 C101(H10A,H10B,H10C), C105(H10J,H10K,H10L)
;
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.064
_oxdiff_exptl_absorpt_empirical_full_min 0.753
_shelx_res_checksum              80767
_cell_oxdiff_length_a            15.36224(17)
_cell_oxdiff_length_b            25.7235(3)
_cell_oxdiff_length_c            20.8918(2)
_cell_oxdiff_angle_alpha         89.9846(8)
_cell_oxdiff_angle_beta          110.8770(10)
_cell_oxdiff_angle_gamma         90.0199(9)
_cell_oxdiff_volume              7713.84(14)
_cell_oxdiff_measurement_reflns_used 60534