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#$Date: 2016-03-21 17:40:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178789 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/43/4104315.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_4104315
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         'C32 H8 Br4 F14 N2 O4, 3(C6 H6)'
_chemical_formula_sum            'C50 H26 Br4 F14 N2 O4'
_chemical_formula_weight         1304.37
_chemical_name_common
;
?
;
_chemical_name_systematic
; 
?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 115.185(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   27.857(4)
_cell_length_b                   7.1869(10)
_cell_length_c                   13.0085(18)
_cell_measurement_reflns_used    6925
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.83
_cell_volume                     2356.8(6)
_computing_cell_refinement       'Saint+ ver. 7.53A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2008.3 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.53A (Bruker AXS)'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13376
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    3.520
_exptl_absorpt_correction_T_max  0.8436
_exptl_absorpt_correction_T_min  0.4182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2004/1 (Brucker Nonius 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1276
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.374(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.3546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                4365
_reflns_number_total             4631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja901077a_si_001.cif
_cod_data_source_block           1e
_cod_database_code               4104315
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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
N1 N 0.83832(10) 1.0019(4) 0.6509(2) 0.0294(6) Uani 1 1 d . . .
C1 C 0.82434(12) 0.9310(4) 0.5412(3) 0.0283(6) Uani 1 1 d . . .
O1 O 0.77974(9) 0.8786(4) 0.4833(2) 0.0373(5) Uani 1 1 d . . .
C2 C 0.86721(12) 0.9296(4) 0.5023(3) 0.0257(6) Uani 1 1 d . . .
C3 C 0.91913(12) 0.9856(4) 0.5771(3) 0.0244(6) Uani 1 1 d . . .
C4 C 0.93108(12) 1.0477(4) 0.6869(3) 0.0265(6) Uani 1 1 d . . .
C5 C 0.88915(13) 1.0614(5) 0.7272(3) 0.0317(7) Uani 1 1 d . . .
O2 O 0.89628(10) 1.1198(4) 0.8197(2) 0.0393(6) Uani 1 1 d . . .
C6 C 0.85692(12) 0.8666(4) 0.3958(3) 0.0278(6) Uani 1 1 d . . .
H6 H 0.8232 0.8153 0.3490 0.033 Uiso 1 1 calc R . .
C7 C 0.89634(12) 0.8779(4) 0.3559(2) 0.0265(6) Uani 1 1 d . . .
Br1 Br 0.881271(12) 0.75848(7) 0.21604(3) 0.03831(10) Uani 1 1 d . . .
C8 C 0.94582(12) 0.9545(4) 0.4209(3) 0.0239(6) Uani 1 1 d . . .
C9 C 0.95961(12) 0.9820(4) 0.5380(3) 0.0236(6) Uani 1 1 d . . .
C10 C 1.01351(12) 1.0073(4) 0.6179(3) 0.0238(6) Uani 1 1 d . . .
C11 C 1.02215(11) 1.0853(4) 0.7215(3) 0.0264(6) Uani 1 1 d . . .
Br2 Br 1.087695(12) 1.19627(7) 0.81752(3) 0.04022(10) Uani 1 1 d . . .
C12 C 0.98126(12) 1.1058(4) 0.7568(3) 0.0292(6) Uani 1 1 d . . .
H12 H 0.9884 1.1595 0.8286 0.035 Uiso 1 1 calc R . .
C13 C 0.79583(13) 1.0227(5) 0.6879(3) 0.0347(7) Uani 1 1 d . . .
H13A H 0.7619 1.0457 0.6209 0.042 Uiso 1 1 calc R . .
H13B H 0.8034 1.1319 0.7388 0.042 Uiso 1 1 calc R . .
C14 C 0.79042(13) 0.8510(5) 0.7499(3) 0.0331(7) Uani 1 1 d . . .
F1 F 0.83765(9) 0.7691(4) 0.8095(2) 0.0590(6) Uani 1 1 d . . .
F2 F 0.75989(10) 0.7217(3) 0.67709(19) 0.0573(6) Uani 1 1 d . . .
C15 C 0.76680(14) 0.8949(6) 0.8351(3) 0.0414(8) Uani 1 1 d . . .
F3 F 0.72268(11) 0.9937(5) 0.7812(3) 0.0720(8) Uani 1 1 d . . .
F4 F 0.80186(13) 0.9988(4) 0.9181(2) 0.0687(8) Uani 1 1 d . . .
C16 C 0.75325(16) 0.7290(7) 0.8904(3) 0.0536(11) Uani 1 1 d . . .
F5 F 0.79516(13) 0.6215(5) 0.9436(3) 0.0806(9) Uani 1 1 d . . .
F6 F 0.71560(12) 0.6258(5) 0.8164(3) 0.0880(11) Uani 1 1 d . . .
F7 F 0.73705(14) 0.7866(5) 0.9662(3) 0.0912(10) Uani 1 1 d . . .
C1_1 C 0.96197(15) 0.5293(10) 0.6207(6) 0.0377(5) Uiso 0.536(6) 1 d PD A 1
H1_1 H 0.9981 0.5619 0.6436 0.045 Uiso 0.536(6) 1 calc PR A 1
C2_1 C 0.9384(3) 0.5543(10) 0.6954(3) 0.0377(5) Uiso 0.536(6) 1 d PD A 1
H2_1 H 0.9588 0.5997 0.7700 0.045 Uiso 0.536(6) 1 calc PR A 1
C3_1 C 0.8847(3) 0.5123(10) 0.6602(6) 0.0377(5) Uiso 0.536(6) 1 d PD A 1
H3_1 H 0.8682 0.5346 0.7097 0.045 Uiso 0.536(6) 1 calc PR A 1
C4_1 C 0.85519(15) 0.4374(10) 0.5522(7) 0.0377(5) Uiso 0.536(6) 1 d PD A 1
H4_1 H 0.8191 0.4039 0.5295 0.045 Uiso 0.536(6) 1 calc PR A 1
C5_1 C 0.8789(3) 0.4117(9) 0.4775(4) 0.0377(5) Uiso 0.536(6) 1 d PD A 1
H5_1 H 0.8587 0.3641 0.4034 0.045 Uiso 0.536(6) 1 calc PR A 1
C6_1 C 0.9324(3) 0.4563(10) 0.5124(5) 0.0377(5) Uiso 0.536(6) 1 d PD A 1
H6_1 H 0.9487 0.4370 0.4622 0.045 Uiso 0.536(6) 1 calc PR A 1
C1_2 C 0.9564(2) 0.5062(12) 0.5790(7) 0.0377(5) Uiso 0.464(6) 1 d PD A 2
H1_2 H 0.9886 0.5170 0.5709 0.045 Uiso 0.464(6) 1 calc PR A 2
C2_2 C 0.9546(2) 0.5598(11) 0.6806(5) 0.0377(5) Uiso 0.464(6) 1 d PD A 2
H2_2 H 0.9853 0.6093 0.7409 0.045 Uiso 0.464(6) 1 calc PR A 2
C3_2 C 0.9074(4) 0.5404(12) 0.6933(5) 0.0377(5) Uiso 0.464(6) 1 d PD A 2
H3_2 H 0.9064 0.5736 0.7630 0.045 Uiso 0.464(6) 1 calc PR A 2
C4_2 C 0.8618(2) 0.4723(12) 0.6035(9) 0.0377(5) Uiso 0.464(6) 1 d PD A 2
H4_2 H 0.8295 0.4632 0.6113 0.045 Uiso 0.464(6) 1 calc PR A 2
C5_2 C 0.8638(2) 0.4176(11) 0.5022(6) 0.0377(5) Uiso 0.464(6) 1 d PD A 2
H5_2 H 0.8332 0.3673 0.4421 0.045 Uiso 0.464(6) 1 calc PR A 2
C6_2 C 0.9109(4) 0.4369(11) 0.4894(5) 0.0377(5) Uiso 0.464(6) 1 d PD A 2
H6_2 H 0.9121 0.4030 0.4199 0.045 Uiso 0.464(6) 1 calc PR A 2
C1_3 C 0.4877(2) 0.3140(6) -0.0033(8) 0.0508(8) Uiso 0.50 1 d PD B -1
H1_3 H 0.4771 0.4398 -0.0036 0.061 Uiso 0.50 1 calc PR B -1
C2_3 C 0.4540(2) 0.1694(6) -0.0033(8) 0.0508(8) Uiso 0.50 1 d PD B -1
H2_3 H 0.4203 0.1972 -0.0055 0.061 Uiso 0.50 1 calc PR B -1
C3_3 C 0.4699(3) -0.0157(6) -0.0002(9) 0.0508(8) Uiso 0.50 1 d PD B -1
H3_3 H 0.4470 -0.1136 -0.0003 0.061 Uiso 0.50 1 calc PR B -1
C4_3 C 0.5196(3) -0.0565(6) 0.0031(9) 0.0508(8) Uiso 0.50 1 d PD B -1
H4_3 H 0.5307 -0.1822 0.0068 0.061 Uiso 0.50 1 calc PR B -1
C5_3 C 0.5530(2) 0.0875(7) 0.0010(7) 0.0508(8) Uiso 0.50 1 d PD B -1
H5_3 H 0.5865 0.0596 0.0022 0.061 Uiso 0.50 1 calc PR B -1
C6_3 C 0.5368(2) 0.2728(6) -0.0029(7) 0.0508(8) Uiso 0.50 1 d PD B -1
H6_3 H 0.5592 0.3706 -0.0052 0.061 Uiso 0.50 1 calc PR B -1
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
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_3
C1 N1 C5 126.0(2) .
C1 N1 C13 117.3(3) .
C5 N1 C13 116.7(3) .
O1 C1 N1 120.9(3) .
O1 C1 C2 123.4(3) .
N1 C1 C2 115.7(3) .
C6 C2 C3 120.2(3) .
C6 C2 C1 119.7(3) .
C3 C2 C1 120.0(3) .
C4 C3 C2 121.6(3) .
C4 C3 C9 119.5(3) .
C2 C3 C9 118.9(3) .
C12 C4 C3 120.6(3) .
C12 C4 C5 118.9(3) .
C3 C4 C5 120.4(3) .
O2 C5 N1 119.9(3) .
O2 C5 C4 123.9(3) .
N1 C5 C4 116.2(3) .
C2 C6 C7 119.8(3) .
C2 C6 H6 120.1 .
C7 C6 H6 120.1 .
C8 C7 C6 121.9(3) .
C8 C7 Br1 121.5(2) .
C6 C7 Br1 116.2(2) .
C7 C8 C9 117.0(3) .
C7 C8 C10 127.1(3) 2_756
C9 C8 C10 115.9(3) 2_756
C8 C9 C3 119.6(3) .
C8 C9 C10 121.3(3) .
C3 C9 C10 119.1(3) .
C11 C10 C9 117.0(3) .
C11 C10 C8 126.7(3) 2_756
C9 C10 C8 116.2(3) 2_756
C10 C11 C12 122.1(3) .
C10 C11 Br2 122.2(2) .
C12 C11 Br2 115.4(2) .
C4 C12 C11 119.5(3) .
C4 C12 H12 120.3 .
C11 C12 H12 120.3 .
N1 C13 C14 111.7(3) .
N1 C13 H13A 109.3 .
C14 C13 H13A 109.3 .
N1 C13 H13B 109.3 .
C14 C13 H13B 109.3 .
H13A C13 H13B 107.9 .
F2 C14 F1 105.9(3) .
F2 C14 C13 111.4(3) .
F1 C14 C13 111.6(3) .
F2 C14 C15 108.2(3) .
F1 C14 C15 106.7(3) .
C13 C14 C15 112.6(3) .
F3 C15 F4 108.8(4) .
F3 C15 C16 107.9(3) .
F4 C15 C16 107.4(3) .
F3 C15 C14 108.2(3) .
F4 C15 C14 107.9(3) .
C16 C15 C14 116.5(3) .
F6 C16 F7 107.9(3) .
F6 C16 F5 107.8(4) .
F7 C16 F5 107.5(3) .
F6 C16 C15 112.2(3) .
F7 C16 C15 110.0(4) .
F5 C16 C15 111.3(3) .
C6_1 C1_1 C2_1 120.0(2) .
C6_1 C1_1 H1_1 120.0 .
C2_1 C1_1 H1_1 120.0 .
C1_1 C2_1 C3_1 119.9(2) .
C1_1 C2_1 H2_1 120.0 .
C3_1 C2_1 H2_1 120.0 .
C2_1 C3_1 C4_1 120.1(2) .
C2_1 C3_1 H3_1 120.0 .
C4_1 C3_1 H3_1 120.0 .
C3_1 C4_1 C5_1 119.9(2) .
C3_1 C4_1 H4_1 120.0 .
C5_1 C4_1 H4_1 120.0 .
C6_1 C5_1 C4_1 119.9(2) .
C6_1 C5_1 H5_1 120.1 .
C4_1 C5_1 H5_1 120.1 .
C1_1 C6_1 C5_1 120.1(2) .
C1_1 C6_1 H6_1 119.9 .
C5_1 C6_1 H6_1 119.9 .
C6_2 C1_2 C2_2 120.1(2) .
C6_2 C1_2 H1_2 119.9 .
C2_2 C1_2 H1_2 119.9 .
C3_2 C2_2 C1_2 119.9(2) .
C3_2 C2_2 H2_2 120.1 .
C1_2 C2_2 H2_2 120.1 .
C2_2 C3_2 C4_2 120.1(2) .
C2_2 C3_2 H3_2 119.9 .
C4_2 C3_2 H3_2 119.9 .
C3_2 C4_2 C5_2 119.9(2) .
C3_2 C4_2 H4_2 120.0 .
C5_2 C4_2 H4_2 120.0 .
C4_2 C5_2 C6_2 120.0(2) .
C4_2 C5_2 H5_2 120.0 .
C6_2 C5_2 H5_2 120.0 .
C1_2 C6_2 C5_2 120.0(2) .
C1_2 C6_2 H6_2 120.0 .
C5_2 C6_2 H6_2 120.0 .
C6_3 C1_3 C2_3 119.8(2) .
C6_3 C1_3 H1_3 120.1 .
C2_3 C1_3 H1_3 120.1 .
C3_3 C2_3 C1_3 120.2(2) .
C3_3 C2_3 H2_3 119.9 .
C1_3 C2_3 H2_3 119.9 .
C4_3 C3_3 C2_3 119.9(2) .
C4_3 C3_3 H3_3 120.0 .
C2_3 C3_3 H3_3 120.0 .
C3_3 C4_3 C5_3 120.1(2) .
C3_3 C4_3 H4_3 119.9 .
C5_3 C4_3 H4_3 119.9 .
C4_3 C5_3 C6_3 119.9(2) .
C4_3 C5_3 H5_3 120.1 .
C6_3 C5_3 H5_3 120.0 .
C1_3 C6_3 C5_3 120.1(2) .
C1_3 C6_3 H6_3 120.0 .
C5_3 C6_3 H6_3 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.405(4) .
N1 C5 1.407(4) .
N1 C13 1.463(4) .
C1 O1 1.207(4) .
C1 C2 1.482(4) .
C2 C6 1.368(4) .
C2 C3 1.415(4) .
C3 C4 1.395(4) .
C3 C9 1.421(4) .
C4 C12 1.369(5) .
C4 C5 1.473(4) .
C5 O2 1.207(4) .
C6 C7 1.403(4) .
C6 H6 0.9500 .
C7 C8 1.388(4) .
C7 Br1 1.890(3) .
C8 C9 1.418(4) .
C8 C10 1.472(4) 2_756
C9 C10 1.428(4) .
C10 C11 1.383(4) .
C10 C8 1.472(4) 2_756
C11 C12 1.405(4) .
C11 Br2 1.895(3) .
C12 H12 0.9500 .
C13 C14 1.517(5) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 F2 1.341(4) .
C14 F1 1.345(4) .
C14 C15 1.543(5) .
C15 F3 1.331(5) .
C15 F4 1.334(5) .
C15 C16 1.521(6) .
C16 F6 1.311(5) .
C16 F7 1.313(5) .
C16 F5 1.324(5) .
C1_1 C6_1 1.3968(19) .
C1_1 C2_1 1.3977(19) .
C1_1 H1_1 0.9500 .
C2_1 C3_1 1.3981(19) .
C2_1 H2_1 0.9500 .
C3_1 C4_1 1.3987(19) .
C3_1 H3_1 0.9500 .
C4_1 C5_1 1.3990(19) .
C4_1 H4_1 0.9500 .
C5_1 C6_1 1.3987(19) .
C5_1 H5_1 0.9500 .
C6_1 H6_1 0.9500 .
C1_2 C6_2 1.3978(19) .
C1_2 C2_2 1.3979(19) .
C1_2 H1_2 0.9500 .
C2_2 C3_2 1.3978(19) .
C2_2 H2_2 0.9500 .
C3_2 C4_2 1.3983(19) .
C3_2 H3_2 0.9500 .
C4_2 C5_2 1.3984(19) .
C4_2 H4_2 0.9500 .
C5_2 C6_2 1.3986(19) .
C5_2 H5_2 0.9500 .
C6_2 H6_2 0.9500 .
C1_3 C6_3 1.3985(19) .
C1_3 C2_3 1.3990(19) .
C1_3 H1_3 0.9500 .
C2_3 C3_3 1.3975(19) .
C2_3 H2_3 0.9500 .
C3_3 C4_3 1.3965(19) .
C3_3 H3_3 0.9500 .
C4_3 C5_3 1.3989(19) .
C4_3 H4_3 0.9500 .
C5_3 C6_3 1.3992(19) .
C5_3 H5_3 0.9500 .
C6_3 H6_3 0.9500 .
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
C5 N1 C1 O1 177.9(3) . .
C13 N1 C1 O1 -4.7(4) . .
C5 N1 C1 C2 -3.4(5) . .
C13 N1 C1 C2 174.1(3) . .
O1 C1 C2 C6 0.1(5) . .
N1 C1 C2 C6 -178.7(3) . .
O1 C1 C2 C3 -177.2(3) . .
N1 C1 C2 C3 4.1(4) . .
C6 C2 C3 C4 -178.9(3) . .
C1 C2 C3 C4 -1.7(4) . .
C6 C2 C3 C9 2.4(4) . .
C1 C2 C3 C9 179.6(3) . .
C2 C3 C4 C12 -178.3(3) . .
C9 C3 C4 C12 0.4(4) . .
C2 C3 C4 C5 -1.7(4) . .
C9 C3 C4 C5 177.0(3) . .
C1 N1 C5 O2 -179.9(3) . .
C13 N1 C5 O2 2.6(5) . .
C1 N1 C5 C4 0.2(5) . .
C13 N1 C5 C4 -177.3(3) . .
C12 C4 C5 O2 -0.8(5) . .
C3 C4 C5 O2 -177.4(3) . .
C12 C4 C5 N1 179.2(3) . .
C3 C4 C5 N1 2.5(4) . .
C3 C2 C6 C7 -7.5(5) . .
C1 C2 C6 C7 175.3(3) . .
C2 C6 C7 C8 -1.0(5) . .
C2 C6 C7 Br1 172.2(2) . .
C6 C7 C8 C9 14.1(4) . .
Br1 C7 C8 C9 -158.7(2) . .
C6 C7 C8 C10 -167.3(3) . 2_756
Br1 C7 C8 C10 19.8(4) . 2_756
C7 C8 C9 C3 -18.9(4) . .
C10 C8 C9 C3 162.4(3) 2_756 .
C7 C8 C9 C10 161.5(3) . .
C10 C8 C9 C10 -17.2(4) 2_756 .
C4 C3 C9 C8 -167.7(3) . .
C2 C3 C9 C8 11.0(4) . .
C4 C3 C9 C10 11.9(4) . .
C2 C3 C9 C10 -169.4(3) . .
C8 C9 C10 C11 161.8(3) . .
C3 C9 C10 C11 -17.8(4) . .
C8 C9 C10 C8 -15.7(4) . 2_756
C3 C9 C10 C8 164.7(3) . 2_756
C9 C10 C11 C12 12.2(4) . .
C8 C10 C11 C12 -170.6(3) 2_756 .
C9 C10 C11 Br2 -160.6(2) . .
C8 C10 C11 Br2 16.6(4) 2_756 .
C3 C4 C12 C11 -6.3(5) . .
C5 C4 C12 C11 177.0(3) . .
C10 C11 C12 C4 -0.2(5) . .
Br2 C11 C12 C4 173.1(2) . .
C1 N1 C13 C14 92.0(3) . .
C5 N1 C13 C14 -90.3(4) . .
N1 C13 C14 F2 -84.7(3) . .
N1 C13 C14 F1 33.5(4) . .
N1 C13 C14 C15 153.4(3) . .
F2 C14 C15 F3 -72.9(4) . .
F1 C14 C15 F3 173.5(3) . .
C13 C14 C15 F3 50.7(4) . .
F2 C14 C15 F4 169.6(3) . .
F1 C14 C15 F4 56.0(4) . .
C13 C14 C15 F4 -66.8(4) . .
F2 C14 C15 C16 48.8(4) . .
F1 C14 C15 C16 -64.8(4) . .
C13 C14 C15 C16 172.4(3) . .
F3 C15 C16 F6 57.6(4) . .
F4 C15 C16 F6 174.7(3) . .
C14 C15 C16 F6 -64.2(5) . .
F3 C15 C16 F7 -62.5(4) . .
F4 C15 C16 F7 54.6(5) . .
C14 C15 C16 F7 175.7(3) . .
F3 C15 C16 F5 178.5(3) . .
F4 C15 C16 F5 -64.4(4) . .
C14 C15 C16 F5 56.7(4) . .
C6_1 C1_1 C2_1 C3_1 -2.2(11) . .
C1_1 C2_1 C3_1 C4_1 2.9(11) . .
C2_1 C3_1 C4_1 C5_1 -2.7(11) . .
C3_1 C4_1 C5_1 C6_1 1.7(11) . .
C2_1 C1_1 C6_1 C5_1 1.3(11) . .
C4_1 C5_1 C6_1 C1_1 -1.1(11) . .
C6_2 C1_2 C2_2 C3_2 1.3(13) . .
C1_2 C2_2 C3_2 C4_2 -1.7(13) . .
C2_2 C3_2 C4_2 C5_2 2.2(12) . .
C3_2 C4_2 C5_2 C6_2 -2.2(12) . .
C2_2 C1_2 C6_2 C5_2 -1.3(13) . .
C4_2 C5_2 C6_2 C1_2 1.7(13) . .
C6_3 C1_3 C2_3 C3_3 1.5(14) . .
C1_3 C2_3 C3_3 C4_3 0.1(13) . .
C2_3 C3_3 C4_3 C5_3 -1.3(10) . .
C3_3 C4_3 C5_3 C6_3 0.9(12) . .
C2_3 C1_3 C6_3 C5_3 -1.9(13) . .
C4_3 C5_3 C6_3 C1_3 0.8(13) . .
