#------------------------------------------------------------------------------
#$Date: 2025-08-20 16:12:52 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301832 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/43/4104316.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4104316
loop_
_publ_author_name
'Rüdiger Schmidt'
'Joon Hak Oh'
'Ya-Sen Sun'
'Manuela Deppisch'
'Ana-Maria Krause'
'Krzysztof Radacki'
'Holger Braunschweig'
'Martin Könemann'
'Peter Erk'
'Zhenan Bao'
'Frank Würthner'
_publ_contact_author_address
; Institut fuer Organische Chemie
Universitaet Wuerzburg
Am Hubland
97074 Wuerzburg, Germany
;
_publ_contact_author_email       wuerthner@chemie.uni-wuerzburg.de
_publ_contact_author_fax         +49-931-8884756
_publ_contact_author_name        'Prof. Dr. Frank Wuerthner'
_publ_contact_author_phone       +49-931-8885340
_publ_section_title
;
 High-Performance Air-Stable n-Channel Organic Thin Film Transistors Based
 on Halogenated Perylene Bisimide Semiconductors
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6215
_journal_page_last               6228
_journal_paper_doi               10.1021/ja901077a
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C36 H6 F12 N2 O4'
_chemical_formula_sum            'C36 H6 F12 N2 O4'
_chemical_formula_weight         758.43
_chemical_name_common
;
perylen
;
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.880(2)
_cell_length_b                   8.5607(6)
_cell_length_c                   10.1357(7)
_cell_measurement_reflns_used    9288
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.56
_cell_volume                     2766.2(3)
_computing_cell_refinement       'Saint+ ver. 7.12A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 1.0-27 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.12A (Bruker AXS)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            39506
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.03
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.7691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2004/1 (Brucker Nonius 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+2.1931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                2784
_reflns_number_total             3272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja901077a_si_002.cif
_cod_data_source_block           2b
_cod_original_sg_symbol_Hall     ' '
_cod_database_code               4104316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.96703(7) 0.2500 0.7500 0.0202(5) Uani 1 2 d S . .
F2 F 1.00893(4) 0.2500 0.7500 0.0275(3) Uani 1 2 d S . .
C3 C 0.94555(5) 0.35200(18) 0.66948(16) 0.0190(3) Uani 1 1 d . . .
F4 F 0.96668(3) 0.45075(11) 0.59212(10) 0.0254(2) Uani 1 1 d . . .
C5 C 0.90229(5) 0.35093(18) 0.66967(15) 0.0180(3) Uani 1 1 d . . .
F6 F 0.88174(3) 0.44950(11) 0.59007(9) 0.0222(2) Uani 1 1 d . . .
C7 C 0.87998(6) 0.2500 0.7500 0.0171(4) Uani 1 2 d S . .
N8 N 0.83509(6) 0.2500 0.7500 0.0187(4) Uani 1 2 d S . .
C9 C 0.81481(5) 0.29055(19) 0.86869(15) 0.0188(3) Uani 1 1 d . . .
O10 O 0.83506(3) 0.33029(14) 0.96406(11) 0.0228(3) Uani 1 1 d . . .
C11 C 0.76852(5) 0.28195(19) 0.86713(15) 0.0190(3) Uani 1 1 d . B .
C12 C 0.74634(7) 0.2500 0.7500 0.0179(4) Uani 1 2 d S . .
C13 C 0.70153(7) 0.2500 0.7500 0.0169(4) Uani 1 2 d S . .
C14 C 0.67956(5) 0.28410(18) 0.86996(15) 0.0175(3) Uani 1 1 d . . .
C16 C 0.74715(5) 0.3083(2) 0.98239(16) 0.0232(4) Uani 1 1 d . . .
H16A H 0.7622 0.3266 1.0619 0.028 Uiso 1 1 calc R A 1
C15A C 0.70354(5) 0.3081(2) 0.98300(16) 0.0225(3) Uani 0.482(3) 1 d P B 1
F17A F 0.68654(6) 0.3359(3) 1.1013(2) 0.0315(7) Uani 0.482(3) 1 d P B 1
C23A C 0.60966(5) 0.3384(2) 0.97563(16) 0.0203(3) Uani 0.482(3) 1 d P B 1
H23A H 0.6238 0.3684 1.0541 0.024 Uiso 0.482(3) 1 calc PR B 1
C15B C 0.70354(5) 0.3081(2) 0.98300(16) 0.0225(3) Uani 0.518(3) 1 d P B 2
H15B H 0.6894 0.3252 1.0643 0.027 Uiso 0.518(3) 1 calc PR B 2
C23B C 0.60966(5) 0.3384(2) 0.97563(16) 0.0203(3) Uani 0.518(3) 1 d P B 2
F17B F 0.62674(5) 0.3728(2) 1.09021(17) 0.0238(5) Uani 0.518(3) 1 d P B 2
C18 C 0.63357(5) 0.29285(17) 0.86800(15) 0.0162(3) Uani 1 1 d . B .
C19 C 0.61174(6) 0.2500 0.7500 0.0156(4) Uani 1 2 d S . .
C20 C 0.56691(6) 0.2500 0.7500 0.0156(4) Uani 1 2 d S . .
C21 C 0.54479(5) 0.29813(17) 0.86337(15) 0.0169(3) Uani 1 1 d . . .
C22 C 0.56598(5) 0.34251(19) 0.97473(16) 0.0198(3) Uani 1 1 d . B .
H22A H 0.5510 0.3758 1.0507 0.024 Uiso 1 1 calc R C 1
C24 C 0.49846(5) 0.30056(18) 0.86608(16) 0.0180(3) Uani 1 1 d . B .
O25 O 0.47783(3) 0.34201(14) 0.95944(11) 0.0222(3) Uani 1 1 d . . .
N26 N 0.47825(5) 0.2500 0.7500 0.0191(4) Uani 1 2 d S . .
C27 C 0.43344(7) 0.2500 0.7500 0.0223(5) Uani 1 2 d S . .
C28 C 0.41141(5) 0.3815(2) 0.71259(17) 0.0270(4) Uani 1 1 d . . .
F29 F 0.43198(3) 0.51051(13) 0.67761(11) 0.0348(3) Uani 1 1 d . B .
C30 C 0.36800(6) 0.3815(3) 0.71138(18) 0.0359(5) Uani 1 1 d . B .
F31 F 0.34697(4) 0.50887(19) 0.67310(12) 0.0528(4) Uani 1 1 d . . .
C32 C 0.34697(7) 0.2500 0.7500 0.0391(8) Uani 1 2 d S . .
F33 F 0.30467(5) 0.2500 0.7500 0.0592(7) Uani 1 2 d S B .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
F2 C1 C3 119.81(10) . .
F2 C1 C3 119.81(10) . 4_556
C3 C1 C3 120.4(2) . 4_556
F4 C3 C1 119.90(14) . .
F4 C3 C5 120.63(14) . .
C1 C3 C5 119.48(15) . .
F6 C5 C3 118.97(14) . .
F6 C5 C7 119.78(14) . .
C3 C5 C7 121.25(14) . .
C5 C7 C5 118.16(19) . 4_556
C5 C7 N8 120.92(10) . .
C5 C7 N8 120.92(10) 4_556 .
C9 N8 C9 125.40(18) 4_556 .
C9 N8 C7 117.30(9) 4_556 .
C9 N8 C7 117.30(9) . .
O10 C9 N8 120.41(14) . .
O10 C9 C11 123.70(14) . .
N8 C9 C11 115.89(13) . .
C16 C11 C12 120.05(14) . .
C16 C11 C9 118.61(14) . .
C12 C11 C9 121.33(14) . .
C11 C12 C11 119.74(19) . 4_556
C11 C12 C13 120.13(10) . .
C11 C12 C13 120.13(10) 4_556 .
C12 C13 C14 119.26(9) . 4_556
C12 C13 C14 119.26(9) . .
C14 C13 C14 121.48(19) 4_556 .
C15A C14 C13 117.37(14) . .
C15A C14 C18 123.49(14) . .
C13 C14 C18 119.14(14) . .
C11 C16 C15A 120.03(15) . .
C11 C16 H16A 120.0 . .
C15A C16 H16A 120.0 . .
F17A C15A C16 114.14(16) . .
F17A C15A C14 122.79(16) . .
C16 C15A C14 123.05(14) . .
C18 C23A C22 123.46(14) . .
C18 C23A H23A 118.3 . .
C22 C23A H23A 118.3 . .
C23A C18 C19 117.53(14) . .
C23A C18 C14 123.54(14) . .
C19 C18 C14 118.92(14) . .
C20 C19 C18 119.08(9) . .
C20 C19 C18 119.09(9) . 4_556
C18 C19 C18 121.83(18) . 4_556
C21 C20 C21 119.97(19) 4_556 .
C21 C20 C19 120.01(9) 4_556 .
C21 C20 C19 120.01(9) . .
C22 C21 C20 120.41(14) . .
C22 C21 C24 118.29(14) . .
C20 C21 C24 121.29(14) . .
C21 C22 C23A 119.45(14) . .
C21 C22 H22A 120.3 . .
C23A C22 H22A 120.3 . .
O25 C24 N26 119.75(14) . .
O25 C24 C21 124.33(14) . .
N26 C24 C21 115.92(14) . .
C24 N26 C24 125.61(18) 4_556 .
C24 N26 C27 117.20(9) 4_556 .
C24 N26 C27 117.20(9) . .
C28 C27 C28 118.8(2) . 4_556
C28 C27 N26 120.59(11) . .
C28 C27 N26 120.60(11) 4_556 .
F29 C28 C27 119.92(15) . .
F29 C28 C30 119.30(17) . .
C27 C28 C30 120.78(19) . .
F31 C30 C32 120.56(16) . .
F31 C30 C28 120.3(2) . .
C32 C30 C28 119.16(19) . .
F33 C32 C30 119.35(11) . 4_556
F33 C32 C30 119.35(11) . .
C30 C32 C30 121.3(2) 4_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 F2 1.335(2) .
C1 C3 1.3775(19) .
C1 C3 1.3775(19) 4_556
C3 F4 1.3353(18) .
C3 C5 1.379(2) .
C5 F6 1.3386(17) .
C5 C7 1.3839(19) .
C7 C5 1.3839(19) 4_556
C7 N8 1.431(3) .
N8 C9 1.4090(17) 4_556
N8 C9 1.4091(17) .
C9 O10 1.2111(19) .
C9 C11 1.478(2) .
C11 C16 1.371(2) .
C11 C12 1.4087(18) .
C12 C11 1.4087(19) 4_556
C12 C13 1.428(3) .
C13 C14 1.4333(18) 4_556
C13 C14 1.4333(18) .
C14 C15A 1.393(2) .
C14 C18 1.468(2) .
C16 C15A 1.390(2) .
C16 H16A 0.9500 .
C15A F17A 1.337(3) .
C23A C18 1.387(2) .
C23A C22 1.393(2) .
C23A H23A 0.9500 .
C18 C19 1.4315(18) .
C19 C20 1.429(3) .
C19 C18 1.4316(18) 4_556
C20 C21 1.4098(18) 4_556
C20 C21 1.4098(18) .
C21 C22 1.369(2) .
C21 C24 1.477(2) .
C22 H22A 0.9500 .
C24 O25 1.2057(19) .
C24 N26 1.4095(17) .
N26 C24 1.4095(17) 4_556
N26 C27 1.429(3) .
C27 C28 1.380(2) .
C27 C28 1.380(2) 4_556
C28 F29 1.333(2) .
C28 C30 1.384(2) .
C30 F31 1.337(2) .
C30 C32 1.368(3) .
C32 F33 1.348(3) .
C32 C30 1.368(3) 4_556
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
F2 C1 C3 F4 -0.22(16) . .
C3 C1 C3 F4 179.78(16) 4_556 .
F2 C1 C3 C5 179.77(10) . .
C3 C1 C3 C5 -0.23(10) 4_556 .
F4 C3 C5 F6 0.6(2) . .
C1 C3 C5 F6 -179.35(12) . .
F4 C3 C5 C7 -179.54(12) . .
C1 C3 C5 C7 0.5(2) . .
F6 C5 C7 C5 179.58(16) . 4_556
C3 C5 C7 C5 -0.24(11) . 4_556
F6 C5 C7 N8 -0.42(16) . .
C3 C5 C7 N8 179.77(11) . .
C5 C7 N8 C9 62.79(10) . 4_556
C5 C7 N8 C9 -117.20(10) 4_556 4_556
C5 C7 N8 C9 -117.20(10) . .
C5 C7 N8 C9 62.80(10) 4_556 .
C9 N8 C9 O10 -176.76(17) 4_556 .
C7 N8 C9 O10 3.24(17) . .
C9 N8 C9 C11 2.86(10) 4_556 .
C7 N8 C9 C11 -177.14(10) . .
O10 C9 C11 C16 -5.3(3) . .
N8 C9 C11 C16 175.04(14) . .
O10 C9 C11 C12 173.62(14) . .
N8 C9 C11 C12 -6.0(2) . .
C16 C11 C12 C11 -177.95(18) . 4_556
C9 C11 C12 C11 3.10(10) . 4_556
C16 C11 C12 C13 2.06(18) . .
C9 C11 C12 C13 -176.90(10) . .
C11 C12 C13 C14 -179.47(10) . 4_556
C11 C12 C13 C14 0.53(10) 4_556 4_556
C11 C12 C13 C14 0.53(10) . .
C11 C12 C13 C14 -179.47(10) 4_556 .
C12 C13 C14 C15A -3.13(16) . .
C14 C13 C14 C15A 176.87(16) 4_556 .
C12 C13 C14 C18 176.54(10) . .
C14 C13 C14 C18 -3.46(10) 4_556 .
C12 C11 C16 C15A -1.9(2) . .
C9 C11 C16 C15A 177.06(16) . .
C11 C16 C15A F17A -179.72(19) . .
C11 C16 C15A C14 -0.9(3) . .
C13 C14 C15A F17A -177.86(18) . .
C18 C14 C15A F17A 2.5(3) . .
C13 C14 C15A C16 3.4(2) . .
C18 C14 C15A C16 -176.26(16) . .
C22 C23A C18 C19 0.8(2) . .
C22 C23A C18 C14 -178.17(15) . .
C15A C14 C18 C23A 5.5(2) . .
C13 C14 C18 C23A -174.13(13) . .
C15A C14 C18 C19 -173.44(14) . .
C13 C14 C18 C19 6.91(19) . .
C23A C18 C19 C20 -2.47(16) . .
C14 C18 C19 C20 176.55(9) . .
C23A C18 C19 C18 177.53(16) . 4_556
C14 C18 C19 C18 -3.45(9) . 4_556
C18 C19 C20 C21 -177.33(10) . 4_556
C18 C19 C20 C21 2.67(10) 4_556 4_556
C18 C19 C20 C21 2.67(10) . .
C18 C19 C20 C21 -177.33(10) 4_556 .
C21 C20 C21 C22 178.87(16) 4_556 .
C19 C20 C21 C22 -1.13(16) . .
C21 C20 C21 C24 -0.47(10) 4_556 .
C19 C20 C21 C24 179.53(10) . .
C20 C21 C22 C23A -0.6(2) . .
C24 C21 C22 C23A 178.77(14) . .
C18 C23A C22 C21 0.8(3) . .
C22 C21 C24 O25 1.5(2) . .
C20 C21 C24 O25 -179.18(13) . .
C22 C21 C24 N26 -178.45(13) . .
C20 C21 C24 N26 0.90(19) . .
O25 C24 N26 C24 179.65(17) . 4_556
C21 C24 N26 C24 -0.43(9) . 4_556
O25 C24 N26 C27 -0.35(17) . .
C21 C24 N26 C27 179.57(9) . .
C24 N26 C27 C28 -91.58(11) 4_556 .
C24 N26 C27 C28 88.42(11) . .
C24 N26 C27 C28 88.42(11) 4_556 4_556
C24 N26 C27 C28 -91.57(11) . 4_556
C28 C27 C28 F29 179.17(17) 4_556 .
N26 C27 C28 F29 -0.83(17) . .
C28 C27 C28 C30 -0.55(12) 4_556 .
N26 C27 C28 C30 179.45(12) . .
F29 C28 C30 F31 1.3(2) . .
C27 C28 C30 F31 -179.02(13) . .
F29 C28 C30 C32 -178.63(13) . .
C27 C28 C30 C32 1.1(2) . .
F31 C30 C32 F33 -0.42(18) . .
C28 C30 C32 F33 179.46(11) . .
F31 C30 C32 C30 179.58(18) . 4_556
C28 C30 C32 C30 -0.54(11) . 4_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 57764089
