# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a
#TrackingRef 'a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 Br F3 N2 O4'
_chemical_formula_sum            'C23 H16 Br F3 N2 O4'
_chemical_formula_weight         521.29
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.0616(16)
_cell_length_b                   10.147(2)
_cell_length_c                   26.551(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2171.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6431
_cell_measurement_theta_min      2.1488
_cell_measurement_theta_max      27.4703

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    1.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14343
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4940
_reflns_number_gt                4629
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0274P)^2^+0.6280P] where P=(Fo^2^+2Fc^2^)/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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(7)
_refine_ls_number_reflns         4940
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.74688(4) 0.81553(2) 0.133963(12) 0.04358(9) Uani 1 1 d . . .
F1 F 0.9775(2) 0.07549(17) 0.22660(7) 0.0507(5) Uani 1 1 d . . .
F2 F 1.18556(19) 0.14446(16) 0.18280(6) 0.0440(4) Uani 1 1 d . . .
F3 F 1.04856(19) 0.28010(16) 0.22980(6) 0.0390(4) Uani 1 1 d . . .
O1 O 0.9304(2) 0.08785(17) 0.12412(7) 0.0358(4) Uani 1 1 d . . .
O2 O 1.2259(2) 0.40643(18) 0.15084(7) 0.0352(4) Uani 1 1 d . . .
O3 O 0.6325(2) 0.12654(19) 0.16164(8) 0.0413(5) Uani 1 1 d . . .
O4 O 0.71467(19) 0.30329(17) 0.20685(7) 0.0335(4) Uani 1 1 d . . .
N1 N 1.1513(4) 0.3785(3) 0.00046(10) 0.0523(7) Uani 1 1 d . . .
N2 N 1.0037(2) 0.5468(2) 0.14343(7) 0.0253(4) Uani 1 1 d . . .
C1 C 1.0345(3) 0.1773(3) 0.19896(10) 0.0358(6) Uani 1 1 d . . .
C2 C 0.9147(3) 0.2028(2) 0.15515(9) 0.0276(5) Uani 1 1 d . . .
C3 C 0.9990(3) 0.1234(3) 0.07962(10) 0.0344(6) Uani 1 1 d . . .
H3 H 1.0270 0.0617 0.0541 0.041 Uiso 1 1 calc R . .
C4 C 1.0237(3) 0.2519(2) 0.07469(9) 0.0285(5) Uani 1 1 d . . .
C5 C 0.9560(3) 0.3250(2) 0.12044(8) 0.0245(5) Uani 1 1 d . . .
C6 C 1.0943(3) 0.3187(3) 0.03277(10) 0.0363(6) Uani 1 1 d . . .
C7 C 1.0807(3) 0.4264(2) 0.14134(9) 0.0258(5) Uani 1 1 d . . .
C8 C 0.8423(3) 0.5413(2) 0.12261(8) 0.0230(5) Uani 1 1 d . . .
C9 C 0.7225(3) 0.6364(2) 0.11506(9) 0.0273(5) Uani 1 1 d . . .
C10 C 0.5739(3) 0.6019(3) 0.09156(10) 0.0310(5) Uani 1 1 d . . .
H10 H 0.4919 0.6676 0.0860 0.037 Uiso 1 1 calc R . .
C11 C 0.5438(3) 0.4741(3) 0.07622(10) 0.0312(5) Uani 1 1 d . . .
H11 H 0.4418 0.4524 0.0603 0.037 Uiso 1 1 calc R . .
C12 C 0.6631(3) 0.3769(2) 0.08410(9) 0.0284(5) Uani 1 1 d . . .
H12 H 0.6439 0.2887 0.0735 0.034 Uiso 1 1 calc R . .
C13 C 0.8094(3) 0.4111(2) 0.10751(9) 0.0236(5) Uani 1 1 d . . .
C14 C 1.0995(3) 0.6638(2) 0.15739(9) 0.0290(5) Uani 1 1 d . . .
H14B H 1.1924 0.6362 0.1794 0.035 Uiso 1 1 calc R . .
H14A H 1.0275 0.7233 0.1773 0.035 Uiso 1 1 calc R . .
C15 C 1.1695(3) 0.7400(2) 0.11322(9) 0.0266(5) Uani 1 1 d . . .
C16 C 1.1534(3) 0.6988(3) 0.06375(10) 0.0341(6) Uani 1 1 d . . .
H16 H 1.0930 0.6208 0.0563 0.041 Uiso 1 1 calc R . .
C17 C 1.2250(4) 0.7710(3) 0.02501(11) 0.0440(7) Uani 1 1 d . . .
H17 H 1.2133 0.7422 -0.0089 0.053 Uiso 1 1 calc R . .
C18 C 1.3131(4) 0.8841(3) 0.03549(13) 0.0472(8) Uani 1 1 d . . .
H18 H 1.3619 0.9331 0.0089 0.057 Uiso 1 1 calc R . .
C19 C 1.3303(3) 0.9261(3) 0.08432(13) 0.0437(7) Uani 1 1 d . . .
H19 H 1.3919 1.0037 0.0914 0.052 Uiso 1 1 calc R . .
C20 C 1.2576(3) 0.8552(2) 0.12368(10) 0.0337(5) Uani 1 1 d . . .
H20 H 1.2682 0.8852 0.1574 0.040 Uiso 1 1 calc R . .
C21 C 0.7343(3) 0.2046(2) 0.17489(9) 0.0291(5) Uani 1 1 d . . .
C22 C 0.5438(3) 0.3250(3) 0.22476(12) 0.0411(6) Uani 1 1 d . . .
H22B H 0.5231 0.2729 0.2557 0.049 Uiso 1 1 calc R . .
H22A H 0.4632 0.2973 0.1987 0.049 Uiso 1 1 calc R . .
C23 C 0.5254(4) 0.4683(3) 0.23552(12) 0.0453(7) Uani 1 1 d . . .
H23A H 0.5364 0.5183 0.2041 0.068 Uiso 1 1 calc R . .
H23C H 0.6117 0.4961 0.2592 0.068 Uiso 1 1 calc R . .
H23B H 0.4159 0.4848 0.2503 0.068 Uiso 1 1 calc 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
Br1 0.04177(13) 0.02151(12) 0.06745(19) -0.00598(12) -0.00170(16) 0.00363(13)
F1 0.0621(11) 0.0405(10) 0.0495(10) 0.0220(9) -0.0048(9) -0.0001(8)
F2 0.0363(8) 0.0433(9) 0.0524(10) 0.0050(8) -0.0053(7) 0.0150(7)
F3 0.0441(8) 0.0437(9) 0.0293(8) 0.0007(7) -0.0050(6) -0.0009(7)
O1 0.0473(10) 0.0205(8) 0.0397(11) -0.0036(8) 0.0059(8) 0.0029(8)
O2 0.0226(8) 0.0400(9) 0.0430(10) 0.0036(8) -0.0038(7) 0.0016(8)
O3 0.0415(10) 0.0352(10) 0.0471(12) -0.0061(9) 0.0078(9) -0.0111(9)
O4 0.0303(9) 0.0324(9) 0.0379(10) -0.0076(8) 0.0036(7) -0.0005(7)
N1 0.0733(19) 0.0470(15) 0.0368(14) -0.0045(12) 0.0151(14) 0.0035(14)
N2 0.0236(9) 0.0250(10) 0.0273(10) -0.0008(8) 0.0003(8) -0.0016(8)
C1 0.0395(13) 0.0313(13) 0.0366(14) 0.0071(12) -0.0013(11) 0.0060(12)
C2 0.0318(11) 0.0229(11) 0.0283(12) -0.0037(10) 0.0007(9) 0.0024(10)
C3 0.0378(13) 0.0325(14) 0.0328(14) -0.0080(11) -0.0004(11) 0.0067(11)
C4 0.0261(11) 0.0315(13) 0.0280(12) -0.0049(11) 0.0005(9) 0.0060(10)
C5 0.0239(9) 0.0245(11) 0.0252(11) 0.0003(10) -0.0002(8) 0.0045(9)
C6 0.0427(13) 0.0364(14) 0.0300(13) -0.0059(13) 0.0050(11) 0.0051(13)
C7 0.0261(10) 0.0290(12) 0.0224(12) 0.0019(10) 0.0005(9) 0.0004(9)
C8 0.0224(10) 0.0220(10) 0.0247(12) 0.0008(9) 0.0019(8) -0.0013(9)
C9 0.0263(12) 0.0220(10) 0.0337(12) 0.0014(9) 0.0037(9) 0.0013(9)
C10 0.0233(11) 0.0315(13) 0.0382(14) 0.0067(11) 0.0041(10) 0.0019(10)
C11 0.0230(11) 0.0356(13) 0.0349(14) 0.0013(11) -0.0030(10) -0.0022(10)
C12 0.0277(11) 0.0268(12) 0.0306(13) -0.0014(10) -0.0016(10) -0.0032(10)
C13 0.0233(10) 0.0235(11) 0.0241(11) 0.0010(10) 0.0019(8) 0.0012(8)
C14 0.0296(11) 0.0298(13) 0.0275(12) -0.0020(11) -0.0028(9) -0.0060(10)
C15 0.0206(10) 0.0250(11) 0.0343(13) 0.0019(10) -0.0007(9) 0.0020(9)
C16 0.0308(11) 0.0389(14) 0.0326(13) 0.0027(12) -0.0010(10) -0.0008(12)
C17 0.0447(16) 0.0522(16) 0.0350(14) 0.0115(13) 0.0037(12) 0.0088(14)
C18 0.0415(15) 0.0429(16) 0.057(2) 0.0232(15) 0.0183(14) 0.0095(13)
C19 0.0325(13) 0.0261(13) 0.072(2) 0.0123(14) 0.0101(14) 0.0030(11)
C20 0.0285(10) 0.0267(11) 0.0459(15) 0.0007(10) -0.0007(12) 0.0004(11)
C21 0.0357(12) 0.0222(10) 0.0296(11) 0.0038(9) 0.0016(10) -0.0020(12)
C22 0.0310(12) 0.0423(16) 0.0501(17) -0.0062(15) 0.0128(12) -0.0009(12)
C23 0.0407(16) 0.0463(17) 0.0488(18) -0.0077(14) 0.0023(13) 0.0064(14)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.896(2) . ?
F1 C1 1.348(3) . ?
F2 C1 1.334(3) . ?
F3 C1 1.331(3) . ?
O1 C3 1.354(3) . ?
O1 C2 1.433(3) . ?
O2 C7 1.214(3) . ?
O3 C21 1.194(3) . ?
O4 C21 1.322(3) . ?
O4 C22 1.474(3) . ?
N1 C6 1.147(4) . ?
N2 C7 1.371(3) . ?
N2 C8 1.415(3) . ?
N2 C14 1.464(3) . ?
C1 C2 1.534(3) . ?
C2 C21 1.546(3) . ?
C2 C5 1.580(3) . ?
C3 C4 1.325(4) . ?
C3 H3 0.9500 . ?
C4 C6 1.422(4) . ?
C4 C5 1.524(3) . ?
C5 C13 1.509(3) . ?
C5 C7 1.542(3) . ?
C8 C9 1.380(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.395(3) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.514(3) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.384(3) . ?
C15 C20 1.395(3) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.372(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C22 C23 1.490(4) . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23C 0.9800 . ?
C23 H23B 0.9800 . ?

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
_geom_angle_publ_flag
C3 O1 C2 108.70(19) . . ?
C21 O4 C22 115.6(2) . . ?
C7 N2 C8 111.45(19) . . ?
C7 N2 C14 119.56(18) . . ?
C8 N2 C14 128.0(2) . . ?
F3 C1 F2 108.4(2) . . ?
F3 C1 F1 107.1(2) . . ?
F2 C1 F1 107.2(2) . . ?
F3 C1 C2 112.8(2) . . ?
F2 C1 C2 111.9(2) . . ?
F1 C1 C2 109.1(2) . . ?
O1 C2 C1 104.1(2) . . ?
O1 C2 C21 106.71(19) . . ?
C1 C2 C21 109.7(2) . . ?
O1 C2 C5 106.54(19) . . ?
C1 C2 C5 116.2(2) . . ?
C21 C2 C5 112.73(19) . . ?
C4 C3 O1 114.2(2) . . ?
C4 C3 H3 122.9 . . ?
O1 C3 H3 122.9 . . ?
C3 C4 C6 127.3(2) . . ?
C3 C4 C5 110.2(2) . . ?
C6 C4 C5 122.4(2) . . ?
C13 C5 C4 112.40(19) . . ?
C13 C5 C7 101.86(18) . . ?
C4 C5 C7 112.20(19) . . ?
C13 C5 C2 114.98(19) . . ?
C4 C5 C2 99.11(19) . . ?
C7 C5 C2 116.82(19) . . ?
N1 C6 C4 176.4(3) . . ?
O2 C7 N2 125.2(2) . . ?
O2 C7 C5 126.3(2) . . ?
N2 C7 C5 108.28(18) . . ?
C9 C8 C13 118.9(2) . . ?
C9 C8 N2 132.3(2) . . ?
C13 C8 N2 108.8(2) . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 Br1 124.02(18) . . ?
C10 C9 Br1 116.59(17) . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C8 121.8(2) . . ?
C12 C13 C5 128.8(2) . . ?
C8 C13 C5 109.4(2) . . ?
N2 C14 C15 114.51(19) . . ?
N2 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
N2 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
H14B C14 H14A 107.6 . . ?
C16 C15 C20 119.3(2) . . ?
C16 C15 C14 123.1(2) . . ?
C20 C15 C14 117.6(2) . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 119.7(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O3 C21 O4 127.5(2) . . ?
O3 C21 C2 122.6(2) . . ?
O4 C21 C2 109.8(2) . . ?
O4 C22 C23 107.5(2) . . ?
O4 C22 H22B 110.2 . . ?
C23 C22 H22B 110.2 . . ?
O4 C22 H22A 110.2 . . ?
C23 C22 H22A 110.2 . . ?
H22B C22 H22A 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?

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
C3 O1 C2 C1 -113.9(2) . . . . ?
C3 O1 C2 C21 130.2(2) . . . . ?
C3 O1 C2 C5 9.5(2) . . . . ?
F3 C1 C2 O1 174.2(2) . . . . ?
F2 C1 C2 O1 51.6(3) . . . . ?
F1 C1 C2 O1 -66.8(2) . . . . ?
F3 C1 C2 C21 -72.0(3) . . . . ?
F2 C1 C2 C21 165.4(2) . . . . ?
F1 C1 C2 C21 47.0(3) . . . . ?
F3 C1 C2 C5 57.4(3) . . . . ?
F2 C1 C2 C5 -65.2(3) . . . . ?
F1 C1 C2 C5 176.4(2) . . . . ?
C2 O1 C3 C4 -4.0(3) . . . . ?
O1 C3 C4 C6 179.5(2) . . . . ?
O1 C3 C4 C5 -3.6(3) . . . . ?
C3 C4 C5 C13 -113.3(2) . . . . ?
C6 C4 C5 C13 63.8(3) . . . . ?
C3 C4 C5 C7 132.6(2) . . . . ?
C6 C4 C5 C7 -50.3(3) . . . . ?
C3 C4 C5 C2 8.7(3) . . . . ?
C6 C4 C5 C2 -174.3(2) . . . . ?
O1 C2 C5 C13 109.4(2) . . . . ?
C1 C2 C5 C13 -135.1(2) . . . . ?
C21 C2 C5 C13 -7.3(3) . . . . ?
O1 C2 C5 C4 -10.6(2) . . . . ?
C1 C2 C5 C4 104.8(2) . . . . ?
C21 C2 C5 C4 -127.3(2) . . . . ?
O1 C2 C5 C7 -131.2(2) . . . . ?
C1 C2 C5 C7 -15.8(3) . . . . ?
C21 C2 C5 C7 112.0(2) . . . . ?
C3 C4 C6 N1 -171(5) . . . . ?
C5 C4 C6 N1 13(5) . . . . ?
C8 N2 C7 O2 170.6(2) . . . . ?
C14 N2 C7 O2 0.9(4) . . . . ?
C8 N2 C7 C5 -4.4(3) . . . . ?
C14 N2 C7 C5 -174.10(19) . . . . ?
C13 C5 C7 O2 -169.9(2) . . . . ?
C4 C5 C7 O2 -49.5(3) . . . . ?
C2 C5 C7 O2 63.9(3) . . . . ?
C13 C5 C7 N2 5.0(2) . . . . ?
C4 C5 C7 N2 125.4(2) . . . . ?
C2 C5 C7 N2 -121.1(2) . . . . ?
C7 N2 C8 C9 -177.6(2) . . . . ?
C14 N2 C8 C9 -9.0(4) . . . . ?
C7 N2 C8 C13 1.8(3) . . . . ?
C14 N2 C8 C13 170.4(2) . . . . ?
C13 C8 C9 C10 -1.6(4) . . . . ?
N2 C8 C9 C10 177.8(2) . . . . ?
C13 C8 C9 Br1 179.29(17) . . . . ?
N2 C8 C9 Br1 -1.4(4) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
Br1 C9 C10 C11 179.9(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C8 -1.3(4) . . . . ?
C11 C12 C13 C5 179.7(2) . . . . ?
C9 C8 C13 C12 1.9(4) . . . . ?
N2 C8 C13 C12 -177.6(2) . . . . ?
C9 C8 C13 C5 -178.9(2) . . . . ?
N2 C8 C13 C5 1.6(3) . . . . ?
C4 C5 C13 C12 54.9(3) . . . . ?
C7 C5 C13 C12 175.2(2) . . . . ?
C2 C5 C13 C12 -57.5(3) . . . . ?
C4 C5 C13 C8 -124.2(2) . . . . ?
C7 C5 C13 C8 -3.9(2) . . . . ?
C2 C5 C13 C8 123.4(2) . . . . ?
C7 N2 C14 C15 93.6(3) . . . . ?
C8 N2 C14 C15 -74.1(3) . . . . ?
N2 C14 C15 C16 -3.8(3) . . . . ?
N2 C14 C15 C20 177.9(2) . . . . ?
C20 C15 C16 C17 0.4(4) . . . . ?
C14 C15 C16 C17 -177.9(2) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
C14 C15 C20 C19 177.4(2) . . . . ?
C18 C19 C20 C15 1.0(4) . . . . ?
C22 O4 C21 O3 -5.4(4) . . . . ?
C22 O4 C21 C2 174.1(2) . . . . ?
O1 C2 C21 O3 -5.1(3) . . . . ?
C1 C2 C21 O3 -117.2(3) . . . . ?
C5 C2 C21 O3 111.5(3) . . . . ?
O1 C2 C21 O4 175.46(19) . . . . ?
C1 C2 C21 O4 63.3(3) . . . . ?
C5 C2 C21 O4 -67.9(2) . . . . ?
C21 O4 C22 C23 -150.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.050


_database_code_depnum_ccdc_archive 'CCDC 934201'