# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2014



data_global
_journal_name_full               ChemCatChem
_journal_coden_cambridge         1453
#TrackingRef 'web_deposit_cif_file_0_AlexanderPoethig_1362646989.Compound_10_fine.cif'

#==============================================================================

# 0. AUDIT DETAILS

_audit_creation_date             'Mar 04 16:27:58 2013'
_audit_creation_method           'PLATON <TABLE ACC> option'
_audit_update_record             
;
04-Mar-13 Updated by the Author A.P.
Text writing by A.P.
Checkcif OK
08-Mar-13 Updated by the Author A.P.
;

#===============================================================================

# 1. SUBMISSION DETAILS

# Name and address of author for X-ray correspondence

_publ_contact_author_name        # Name of author for correspondence
;
Dr. Alexander Pöthig
;
_publ_contact_author_address     # address of author for correspondence
;
Catalysis Research Center
Technische Universit/"at M/"unchen
Ernst-Otto-Fischer-Str. 1
85747 Garching bei M/"unchen
Germany
;

_publ_contact_author_email       alexander.poethig@tum.de
_publ_contact_author_fax         '+49(0)89 289 13473'
_publ_contact_author_phone       '+49(0)89 289 13133'

_publ_requested_category         ?
_publ_requested_coeditor_name    ?

_publ_contact_letter             # Include date of submission
;
Date of submission: March 2013
;

#===============================================================================

# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)

#===============================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
;
_publ_section_title_footnote     
;
;

# The loop structure below should contain the names and adresses of all
# authors, in the required order of publication. Repeat as necessary.


loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Anthofer, M. H.'
; # author related footnote
?
;
;
Catalysis Research Center
Inorganic Chemistry / Molecular Catalysis
Technische Universit/"at M/"unchen
Ernst-Otto-Fischer-Str. 1
85747 Garching bei M/"unchen
Germany
;
'Wilhelm, M. E.'
; # author related footnote
?
;
;
Catalysis Research Center
Inorganic Chemistry / Molecular Catalysis
Technische Universit/"at M/"unchen
Ernst-Otto-Fischer-Str. 1
85747 Garching bei M/"unchen
Germany
;
'Markovits, I. E.'
; # author related footnote
?
;
;
Catalysis Research Center
Inorganic Chemistry / Molecular Catalysis
Technische Universit/"at M/"unchen
Ernst-Otto-Fischer-Str. 1
85747 Garching bei M/"unchen
Germany
;
'Poethig, A.'
; # author related footnote
?
;
;
Catalysis Research Center
Inorganic Chemistry / Molecular Catalysis
Technische Universit/"at M/"unchen
Ernst-Otto-Fischer-Str. 1
85747 Garching bei M/"unchen
Germany
;
'Cokoja, M.'
; # author related footnote
?
;
;
Catalysis Research Center
Inorganic Chemistry / Molecular Catalysis
Technische Universit/"at M/"unchen
Ernst-Otto-Fischer-Str. 1
85747 Garching bei M/"unchen
Germany
;
#===============================================================================

# 4. TEXT

_publ_section_abstract           
;
The synthesis and characterization of a library of imidazolium-based...
;

# Insert blank lines between paragraphs

_publ_section_comment            
;
;
_publ_section_exptl_prep         
;
The crystal was fixed on the top of a glas fiber with
perfluorinated ether and transferred to the diffractometer.
;
_publ_section_exptl_refinement   
;
Solution and refinements with the program SHELXS97 and SHELXL97
(Sheldrick, 1997)in conjunction with SHELXLE (Huebschle, 2011).
Hydrogen atoms could not be located in the difference Fourier maps
and were calculated in ideal positions (riding model).
;

# Insert blank lines between references

_publ_section_references         
;
Allen, F. H.(2004). ENCIFER. J. Applied Cryst. 37, 335-338.

Bruker (2008a). APEX suite of crystallographic software.
APEX 2 Version 2008.4. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2008b). SAINT, Version 7.56a and SADABS Version 2008/1.
Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H.D. (1983). Acta Cryst. A39, 876-881.

Huebschle, C. B.; Sheldrick, G. M.; Dittrich, B. (2011). SHELXLE.
J. Appl. Cryst., 44, (2011) 1281 - 1284.

Sheldrick, G. M. (1997). SHELXS97. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.

Spek, A. L. (2011). PLATON, A Multipurpose Crystallographic Tool, Utrecht
University, Utrecht, The Netherlands.

Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.

Wilson, A.J.C. (1992). Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;

_publ_section_acknowledgements   
;
;
_publ_section_figure_captions    
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;

#===============================================================================

data_Compound_10
#TrackingRef 'web_deposit_cif_file_0_AlexanderPoethig_1362646989.Compound_10_fine.cif'


#===============================================================================

# 5. CHEMICAL DATA

_chemical_formula_moiety         'C18 H22 F5 N2, Br'
_chemical_formula_sum            'C18 H22 Br F5 N2'
_chemical_formula_weight         441.28
_chemical_compound_source        'see text'

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'
Br Br -0.2901 2.4595 ' 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'
N N 0.0061 0.0033 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   7.8536(3)
_cell_length_b                   8.5571(3)
_cell_length_c                   29.1438(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.415(2)
_cell_angle_gamma                90
_cell_volume                     1958.53(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123
_cell_measurement_reflns_used    3666
_cell_measurement_theta_min      2.4806
_cell_measurement_theta_max      25.3341

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    2.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2008b'
_exptl_absorpt_correction_T_min  0.542
_exptl_absorpt_correction_T_max  0.927

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator A. Poethig
scanspeed 30 s per frame
dx 60 mm
1652 frames measured in 4 data sets
phi-scans with delta_phi = 0.5
omega-scans with delta_omega = 0.5
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_monochromator  'MONTEL optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker APEX-II CCD '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CCD plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            15259
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.1306
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3572
# number of observed reflections (> n sig(I))
_reflns_number_gt                2270
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX II Control Software (Bruker, 2008a)'
_computing_cell_refinement       'SAINT (Bruker, 2008b)'
_computing_data_reduction        'SAINT (Bruker, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 1997), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
Refinement on F² for ALL reflections except those
flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses of fit S
are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The
observed criterion of F² > 2sigma(F²) is used only
for calculating -R-factor-obs etc. and is not
relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice
as large as those based on F, and R-factors based on
ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+4.8085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         3572
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.245
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.121

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

F1 F Uani 0.0839(4) 0.0541(3) 0.15734(10) 1.000 0.0343(11) d . . .
F2 F Uani 0.0556(4) 0.2838(4) 0.09510(10) 1.000 0.0447(12) d . . .
F3 F Uani 0.3382(4) 0.4319(3) 0.06421(10) 1.000 0.0463(14) d . . .
F4 F Uani 0.6502(4) 0.3552(3) 0.09910(10) 1.000 0.0367(11) d . . .
F5 F Uani 0.6790(4) 0.1296(3) 0.16248(9) 1.000 0.0273(11) d . . .
N1 N Uani 0.1617(5) 0.1076(4) 0.29344(15) 1.000 0.0200(16) d . . .
N2 N Uani 0.2888(5) -0.0091(5) 0.23790(12) 1.000 0.0173(12) d . . .
C1 C Uani 0.2519(6) 0.1291(6) 0.25580(18) 1.000 0.0184(17) d . . .
C2 C Uani 0.1424(7) -0.0512(6) 0.30026(18) 1.000 0.0240(19) d . . .
C3 C Uani 0.2229(7) -0.1236(6) 0.26571(18) 1.000 0.0227(19) d . . .
C4 C Uani 0.3981(6) -0.0407(5) 0.19846(16) 1.000 0.0210(17) d . . .
C5 C Uani 0.3811(7) 0.0845(5) 0.16233(17) 1.000 0.0170(17) d . . .
C6 C Uani 0.2280(7) 0.1268(6) 0.14321(17) 1.000 0.0216(19) d . . .
C7 C Uani 0.2107(7) 0.2424(6) 0.11078(18) 1.000 0.0274(19) d . . .
C8 C Uani 0.3542(8) 0.3175(6) 0.09583(18) 1.000 0.028(2) d . . .
C9 C Uani 0.5108(7) 0.2791(6) 0.11304(18) 1.000 0.025(2) d . . .
C10 C Uani 0.5230(7) 0.1636(6) 0.14622(17) 1.000 0.0207(19) d . . .
C11 C Uani 0.0852(7) 0.2307(6) 0.32170(17) 1.000 0.025(2) d . . .
C12 C Uani 0.1372(6) 0.2203(6) 0.37194(17) 1.000 0.0230(19) d . . .
C13 C Uani 0.3252(7) 0.2504(6) 0.38096(16) 1.000 0.0247(19) d . . .
C14 C Uani 0.3738(7) 0.2510(6) 0.43160(17) 1.000 0.0283(19) d . . .
C15 C Uani 0.5562(7) 0.3006(6) 0.44128(17) 1.000 0.030(2) d . . .
C16 C Uani 0.6033(7) 0.2940(7) 0.49197(18) 1.000 0.037(2) d . . .
C17 C Uani 0.7863(8) 0.3428(8) 0.5033(2) 1.000 0.051(3) d . . .
C18 C Uani 0.9135(8) 0.2173(9) 0.4908(2) 1.000 0.070(3) d . . .
Br1 Br Uani 0.68231(7) 0.01427(6) 0.29507(2) 1.000 0.0250(2) d . . .
H1 H Uiso 0.28490 0.22750 0.24360 1.000 0.0220 c R . .
H2 H Uiso 0.08340 -0.10000 0.32470 1.000 0.0290 c R . .
H3 H Uiso 0.23250 -0.23320 0.26130 1.000 0.0270 c R . .
H4A H Uiso 0.36700 -0.14300 0.18500 1.000 0.0250 c R . .
H4B H Uiso 0.51820 -0.04660 0.20890 1.000 0.0250 c R . .
H11A H Uiso -0.04030 0.22330 0.31930 1.000 0.0300 c R . .
H11B H Uiso 0.11960 0.33390 0.30950 1.000 0.0300 c R . .
H12A H Uiso 0.06980 0.29710 0.38960 1.000 0.0280 c R . .
H12B H Uiso 0.10820 0.11490 0.38350 1.000 0.0280 c R . .
H13A H Uiso 0.35610 0.35260 0.36750 1.000 0.0300 c R . .
H13B H Uiso 0.39250 0.16900 0.36520 1.000 0.0300 c R . .
H14A H Uiso 0.29620 0.32240 0.44800 1.000 0.0340 c R . .
H14B H Uiso 0.35650 0.14460 0.44410 1.000 0.0340 c R . .
H15A H Uiso 0.57260 0.40870 0.43000 1.000 0.0370 c R . .
H15B H Uiso 0.63410 0.23180 0.42400 1.000 0.0370 c R . .
H16A H Uiso 0.58570 0.18590 0.50310 1.000 0.0440 c R . .
H16B H Uiso 0.52460 0.36270 0.50910 1.000 0.0440 c R . .
H17A H Uiso 0.81370 0.43980 0.48640 1.000 0.0620 c R . .
H17B H Uiso 0.79590 0.36540 0.53650 1.000 0.0620 c R . .
H18A H Uiso 1.02890 0.25380 0.49800 1.000 0.1050 c R . .
H18B H Uiso 0.90440 0.19460 0.45790 1.000 0.1050 c R . .
H18C H Uiso 0.88950 0.12230 0.50830 1.000 0.1050 c R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0278(19) 0.039(2) 0.036(2) 0.0051(15) -0.0015(16) -0.0062(16)
F2 0.037(2) 0.059(2) 0.038(2) 0.0115(17) -0.0099(18) 0.0095(19)
F3 0.065(3) 0.035(2) 0.039(2) 0.0161(16) 0.0053(18) 0.0059(18)
F4 0.043(2) 0.0321(19) 0.035(2) 0.0029(15) 0.0107(17) -0.0134(18)
F5 0.0240(19) 0.0255(17) 0.0323(19) -0.0029(14) -0.0008(16) -0.0039(15)
N1 0.023(3) 0.017(2) 0.020(3) 0.001(2) 0.001(2) 0.003(2)
N2 0.020(2) 0.012(2) 0.020(2) 0.000(2) 0.0018(19) -0.001(2)
C1 0.017(3) 0.016(3) 0.022(3) 0.000(2) -0.003(3) 0.002(3)
C2 0.028(4) 0.023(3) 0.021(3) 0.006(2) 0.001(3) -0.002(3)
C3 0.030(4) 0.015(3) 0.023(3) 0.001(2) -0.001(3) -0.001(3)
C4 0.021(3) 0.020(3) 0.022(3) -0.002(2) 0.002(3) 0.002(3)
C5 0.021(3) 0.014(3) 0.016(3) -0.005(2) 0.004(3) 0.001(3)
C6 0.023(4) 0.021(3) 0.021(3) -0.003(2) 0.005(3) -0.007(3)
C7 0.029(4) 0.030(3) 0.023(3) 0.002(3) -0.003(3) 0.003(3)
C8 0.051(5) 0.016(3) 0.018(3) 0.007(2) 0.004(3) 0.003(3)
C9 0.028(4) 0.021(3) 0.027(4) -0.003(3) 0.008(3) -0.006(3)
C10 0.024(4) 0.017(3) 0.021(3) -0.007(2) -0.002(3) 0.005(3)
C11 0.027(4) 0.019(3) 0.030(4) -0.004(3) 0.007(3) 0.002(3)
C12 0.027(4) 0.017(3) 0.025(3) -0.003(2) 0.003(3) 0.002(3)
C13 0.036(4) 0.016(3) 0.022(3) -0.002(2) 0.004(3) -0.001(3)
C14 0.041(4) 0.024(3) 0.020(3) -0.001(2) 0.004(3) 0.002(3)
C15 0.044(4) 0.024(3) 0.023(4) 0.002(3) 0.002(3) -0.004(3)
C16 0.047(4) 0.035(4) 0.029(4) -0.004(3) -0.003(3) 0.006(3)
C17 0.058(5) 0.057(5) 0.039(4) -0.001(3) -0.014(4) -0.008(4)
C18 0.050(5) 0.122(7) 0.037(5) -0.012(4) -0.001(4) -0.008(5)
Br1 0.0277(3) 0.0159(3) 0.0314(3) 0.0029(3) -0.0012(2) -0.0011(3)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.358(6) . . yes
F2 C7 1.345(6) . . yes
F3 C8 1.350(6) . . yes
F4 C9 1.339(6) . . yes
F5 C10 1.342(6) . . yes
N1 C1 1.323(7) . . yes
N1 C2 1.382(6) . . yes
N1 C11 1.468(6) . . yes
N2 C1 1.326(7) . . yes
N2 C3 1.375(7) . . yes
N2 C4 1.465(6) . . yes
C2 C3 1.344(7) . . no
C4 C5 1.507(6) . . no
C5 C6 1.370(8) . . no
C5 C10 1.389(7) . . no
C6 C7 1.374(7) . . no
C7 C8 1.371(8) . . no
C8 C9 1.365(8) . . no
C9 C10 1.386(7) . . no
C11 C12 1.520(7) . . no
C12 C13 1.520(7) . . no
C13 C14 1.522(7) . . no
C14 C15 1.519(8) . . no
C15 C16 1.521(7) . . no
C16 C17 1.530(8) . . no
C17 C18 1.513(10) . . no
C1 H1 0.9500 . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C4 H4A 0.9900 . . no
C4 H4B 0.9900 . . no
C11 H11A 0.9900 . . no
C11 H11B 0.9900 . . no
C12 H12A 0.9900 . . no
C12 H12B 0.9900 . . no
C13 H13A 0.9900 . . no
C13 H13B 0.9900 . . no
C14 H14A 0.9900 . . no
C14 H14B 0.9900 . . no
C15 H15A 0.9900 . . no
C15 H15B 0.9900 . . no
C16 H16A 0.9900 . . no
C16 H16B 0.9900 . . no
C17 H17A 0.9900 . . no
C17 H17B 0.9900 . . no
C18 H18A 0.9800 . . no
C18 H18B 0.9800 . . no
C18 H18C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 108.4(4) . . . yes
C1 N1 C11 126.1(4) . . . yes
C2 N1 C11 125.4(4) . . . yes
C1 N2 C3 108.6(4) . . . yes
C1 N2 C4 127.2(4) . . . yes
C3 N2 C4 123.8(4) . . . yes
N1 C1 N2 108.8(4) . . . yes
N1 C2 C3 107.0(5) . . . yes
N2 C3 C2 107.1(4) . . . yes
N2 C4 C5 111.6(4) . . . yes
C4 C5 C6 123.0(5) . . . no
C4 C5 C10 121.0(5) . . . no
C6 C5 C10 116.0(4) . . . no
F1 C6 C5 119.1(4) . . . yes
F1 C6 C7 117.4(5) . . . yes
C5 C6 C7 123.5(5) . . . no
F2 C7 C6 120.5(5) . . . yes
F2 C7 C8 120.9(5) . . . yes
C6 C7 C8 118.6(5) . . . no
F3 C8 C7 119.0(5) . . . yes
F3 C8 C9 120.3(5) . . . yes
C7 C8 C9 120.7(5) . . . no
F4 C9 C8 120.5(5) . . . yes
F4 C9 C10 120.4(5) . . . yes
C8 C9 C10 119.1(5) . . . no
F5 C10 C5 120.5(4) . . . yes
F5 C10 C9 117.3(5) . . . yes
C5 C10 C9 122.2(5) . . . no
N1 C11 C12 113.0(4) . . . yes
C11 C12 C13 114.3(4) . . . no
C12 C13 C14 113.9(4) . . . no
C13 C14 C15 114.3(4) . . . no
C14 C15 C16 113.1(4) . . . no
C15 C16 C17 114.9(5) . . . no
C16 C17 C18 112.0(5) . . . no
N1 C1 H1 126.00 . . . no
N2 C1 H1 126.00 . . . no
N1 C2 H2 127.00 . . . no
C3 C2 H2 126.00 . . . no
N2 C3 H3 126.00 . . . no
C2 C3 H3 126.00 . . . no
N2 C4 H4A 109.00 . . . no
N2 C4 H4B 109.00 . . . no
C5 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
H4A C4 H4B 108.00 . . . no
N1 C11 H11A 109.00 . . . no
N1 C11 H11B 109.00 . . . no
C12 C11 H11A 109.00 . . . no
C12 C11 H11B 109.00 . . . no
H11A C11 H11B 108.00 . . . no
C11 C12 H12A 109.00 . . . no
C11 C12 H12B 109.00 . . . no
C13 C12 H12A 109.00 . . . no
C13 C12 H12B 109.00 . . . no
H12A C12 H12B 108.00 . . . no
C12 C13 H13A 109.00 . . . no
C12 C13 H13B 109.00 . . . no
C14 C13 H13A 109.00 . . . no
C14 C13 H13B 109.00 . . . no
H13A C13 H13B 108.00 . . . no
C13 C14 H14A 109.00 . . . no
C13 C14 H14B 109.00 . . . no
C15 C14 H14A 109.00 . . . no
C15 C14 H14B 109.00 . . . no
H14A C14 H14B 108.00 . . . no
C14 C15 H15A 109.00 . . . no
C14 C15 H15B 109.00 . . . no
C16 C15 H15A 109.00 . . . no
C16 C15 H15B 109.00 . . . no
H15A C15 H15B 108.00 . . . no
C15 C16 H16A 109.00 . . . no
C15 C16 H16B 109.00 . . . no
C17 C16 H16A 108.00 . . . no
C17 C16 H16B 109.00 . . . no
H16A C16 H16B 107.00 . . . no
C16 C17 H17A 109.00 . . . no
C16 C17 H17B 109.00 . . . no
C18 C17 H17A 109.00 . . . no
C18 C17 H17B 109.00 . . . no
H17A C17 H17B 108.00 . . . no
C17 C18 H18A 109.00 . . . no
C17 C18 H18B 109.00 . . . no
C17 C18 H18C 110.00 . . . no
H18A C18 H18B 109.00 . . . no
H18A C18 H18C 110.00 . . . no
H18B C18 H18C 109.00 . . . no

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 1.0(6) . . . . no
C11 N1 C1 N2 -175.4(4) . . . . no
C1 N1 C2 C3 -0.2(6) . . . . no
C11 N1 C2 C3 176.2(5) . . . . no
C1 N1 C11 C12 -125.8(5) . . . . no
C2 N1 C11 C12 58.4(6) . . . . no
C3 N2 C1 N1 -1.4(6) . . . . no
C4 N2 C1 N1 -174.5(4) . . . . no
C1 N2 C3 C2 1.3(6) . . . . no
C4 N2 C3 C2 174.7(4) . . . . no
C1 N2 C4 C5 -35.9(6) . . . . no
C3 N2 C4 C5 151.9(4) . . . . no
N1 C2 C3 N2 -0.7(6) . . . . no
N2 C4 C5 C6 -55.0(6) . . . . no
N2 C4 C5 C10 125.5(5) . . . . no
C4 C5 C6 F1 0.4(7) . . . . no
C4 C5 C6 C7 179.0(5) . . . . no
C10 C5 C6 F1 180.0(4) . . . . no
C10 C5 C6 C7 -1.5(7) . . . . no
C4 C5 C10 F5 0.2(7) . . . . no
C4 C5 C10 C9 180.0(5) . . . . no
C6 C5 C10 F5 -179.4(4) . . . . no
C6 C5 C10 C9 0.4(7) . . . . no
F1 C6 C7 F2 2.1(7) . . . . no
F1 C6 C7 C8 -179.9(4) . . . . no
C5 C6 C7 F2 -176.6(5) . . . . no
C5 C6 C7 C8 1.5(8) . . . . no
F2 C7 C8 F3 -1.5(7) . . . . no
F2 C7 C8 C9 177.6(5) . . . . no
C6 C7 C8 F3 -179.6(4) . . . . no
C6 C7 C8 C9 -0.5(8) . . . . no
F3 C8 C9 F4 0.6(8) . . . . no
F3 C8 C9 C10 178.6(4) . . . . no
C7 C8 C9 F4 -178.5(5) . . . . no
C7 C8 C9 C10 -0.5(8) . . . . no
F4 C9 C10 F5 -1.7(7) . . . . no
F4 C9 C10 C5 178.5(4) . . . . no
C8 C9 C10 F5 -179.7(4) . . . . no
C8 C9 C10 C5 0.5(8) . . . . no
N1 C11 C12 C13 65.9(6) . . . . no
C11 C12 C13 C14 176.0(4) . . . . no
C12 C13 C14 C15 -172.8(4) . . . . no
C13 C14 C15 C16 -177.7(4) . . . . no
C14 C15 C16 C17 179.9(5) . . . . no
C15 C16 C17 C18 -75.6(6) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C1 H1 Br1 0.9500 2.7100 3.652(5) 169.00 2_655 yes
C3 H3 Br1 0.9500 2.8000 3.649(5) 149.00 2_645 yes
C4 H4B Br1 0.9900 2.8600 3.611(5) 133.00 . yes
C4 H4B F5 0.9900 2.3900 2.850(5) 107.00 . yes
C11 H11A Br1 0.9900 2.9000 3.743(5) 143.00 1_455 yes
C13 H13A F5 0.9900 2.5400 3.483(6) 159.00 2_655 yes

#===END


_database_code_depnum_ccdc_archive 'CCDC 928238'
