(Z)-N-[1-(Aziridin-1-yl)-2,2,2-tri­fluoro­ethyl­idene]-4-bromo­aniline

Bunev, A.S.; Vasiliev, M.A.; Ostapenko, G.I.; Peregudov, A.S.; Khrustalev, V.N.

doi:10.1107/S1600536814007867

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o550

doi:10.1107/S1600536814007867

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(Z)-N-[1-(Aziridin-1-yl)-2,2,2-trifluoroethylidene]-4-bromoaniline

Alexander S. Bunev,^a ^* Maksim A. Vasiliev,^a Gennady I. Ostapenko,^a Alexander S. Peregudov ^b and Victor N. Khrustalev ^c

^aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya St, Togliatti 445667, Russian Federation, ^bNMR Laboratory, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation, and ^cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: a.s.bunev@gmail.com

(Received 2 April 2014; accepted 9 April 2014; online 12 April 2014)

The title compound, C₁₀H₈BrF₃N₂, crystallizes with two independent molecules in the asymmetric unit, which can be considered as being related by a pseudo-inversion center, so their conformations are different; the corresponding N=C—N—C torsion angles are 54.6 (5) and −50.5 (5)°. In the crystal, molecules related by translation in [001] interact through short intermolecular Br⋯F contacts [3.276 (2) and 3.284 (2) Å], thus forming two types of crystallographically independent chains.

CCDC reference: 996162

Related literature

For applications of aziridines, see: Tanner (1994 ); Remers & Iyengar (1995 ); Armstrong et al. (1996 ); Katoh et al. (1996 ); Schirmeister (1999a ,b ); McCoull & Davis (2000 ). For the crystal structures of related compounds, see: Chinnakali et al. (1998 ); McLaren & Sweeney (1999 ); Zhu et al. (2006 ); Moragas Solà et al. (2010 ).

Experimental

Crystal data

C₁₀H₈BrF₃N₂
M_r = 293.09
Monoclinic, P 2₁
a = 11.642 (2) Å
b = 8.5455 (16) Å
c = 11.846 (2) Å
β = 116.106 (3)°
V = 1058.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.90 mm⁻¹
T = 120 K
0.30 × 0.25 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.388, T_max = 0.442
13846 measured reflections
6146 independent reflections
5186 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.118
S = 1.01
6146 reflections
289 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.97 e Å⁻³
Δρ_min = −0.86 e Å⁻³
Absolute structure: Flack (1983 ), 2866 Friedel pairs
Absolute structure parameter: 0.025 (11)

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 996162

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814007867/cv5449sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007867/cv5449Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007867/cv5449Isup3.cml

checkCIF report

Comment top

Aziridines are important heterocyclic compounds present in unusual natural products that display strong biological activity (Tanner, 1994; McCoull & Davis, 2000). For instance, azinomycines A and B isolated from the fermentation broth of Streptomyces griseofuscus and (+)-FR900482 isolated from the culture broth of Streptomyces sandaensis are potent antitumor antibiotics that exhibit exceptional activity against various types of mammalian solid tumors. Mitomycin C is an aziridine-containing antibiotic produced by Streptomyces caespitosus, whose antineoplastic activity is associated with the high reactivity of the strained aziridine ring (Remers & Iyengar, 1995; Armstrong et al., 1996; Katoh et al., 1996). Recently novel types of peptidic cysteine protease inhibitors containing aziridine-2,3-dicarboxylic acid have been designed and synthesized (Schirmeister, 1999a,b).

In this work, a new substituted aziridine, C₁₀H₈BrF₃N₂ (I), was prepared by the reaction N-(4-bromophenyl)-2,2,2-trifluoroethenecarbonimidoyl chloride with aziridine at room temperature (Figure 1), and its structure was unambiguously established by the X-ray diffraction study (Figure 2).

The title compound I crystallizes in chiral monoclinic space group P2₁ with two crystallographically independent molecules in the unit cell. The two crystallographically independent molecules represent different conformers distinguishing by rotation of the aziridine substituent around the ordinary (CF₃)C—N bond (the corresponding N1—C1—N2—C3 and N3—C11—N4—C13 totsion angles are 54.6 (5) and –50.5 (5)^o, respectively). The bond lengths and angles in I are in a good agreement with those found in the related compounds (Chinnakali et al., 1998; McLaren & Sweeney, 1999; Zhu et al., 2006; Moragas Solà et al., 2010). The molecule of I is the Z-isomer relative to the double C═N bond. The p-bromo-phenyl substituent is twisted by 38.42 (12) and 39.61 (10)% (for the two crystallographically independent molecules, respectively) relative to the double bond plane. Tha absolute structure of I was objectively determined by the refinement of Flack parameter, which has become equal to 0.025 (11).

In the crystal, the molecules of I form infinite chains along [001] by the intermolecular secondary Br1···F1ⁱ (2.276 (2) Å) and Br2···F5ⁱⁱ (3.284 (2) Å) interactions (Figure 3) [symmetry codes: (i) x, y, 1 + z; (ii) x, y, –1 + z]. The chains consist of the conformationally similar molecules and arranged at van der Waals distances.

Related literature top

For applications of aziridines, see: Tanner (1994); Remers & Iyengar (1995); Armstrong et al. (1996); Katoh et al. (1996); Schirmeister (1999a,b); McCoull & Davis (2000). For the crystal structures of related compounds, see: Chinnakali et al. (1998); McLaren & Sweeney (1999); Zhu et al. (2006); Moragas Solà et al. (2010).

Experimental top

To a mixture of aziridine (1.29 mL, 1.075 g, 25 mmol), triethylamine (3.48 mL, 2.525 g, 25 mmol), and benzene (35 mL) was added slowly (20 min) a solution of N-(4-bromophenyl)-2,2,2-trifluoroethenecarbonimidoyl chloride in benzene (50 mL). The mixture was stirred for 5 h. The triethylamine hydrochloride was filtered, and the solvent was evaporated to give of crude product. Yield is 75%. The single-crystal of the product I was obtained by slow crystallization from EtOAc/Hexane (1:9). M.p. = 324–325 K. IR (KBr), ν/cm^-1: 3408, 1715, 1629, 1492, 1295, 1200, 1155, 996, 828, 531. ¹H NMR (600 MHz, DMSO-d₆, 304 K): 7.56 (d, 2H, J = 8.2), 6.99 (d, 2H, J = 8.7), 2.21 (br. s, 4H). Anal. Calcd for C₁₀H₈BrF₃N₂: C, 33.54; H, 1.41. Found: C, 33.61; H, 1.52.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The synthesis of (Z)-N-[1-(aziridin-1-yl)-2,2,2-trifluoroethylidene]-4-bromoaniline.
	Fig. 2. Molecular structure of I (two crystallographically independent molecules representing the different conformers are shown). Displacement ellipsoids are presented at the 50% probability level. H atoms are depicted as small spheres of arbitrary radius.
	Fig. 3. A portion of the crystal structure of I demonstrating the chains of the molecules extended along [001]. The intermolecular secondary Br···F interactions are depicted by dashed lines.

(Z)-N-[1-(Aziridin-1-yl)-2,2,2-trifluoroethylidene]-4-bromoaniline top

Crystal data top

C₁₀H₈BrF₃N₂	F(000) = 576
M_r = 293.09	D_x = 1.840 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4691 reflections
a = 11.642 (2) Å	θ = 3.1–29.9°
b = 8.5455 (16) Å	µ = 3.90 mm⁻¹
c = 11.846 (2) Å	T = 120 K
β = 116.106 (3)°	Prism, colourless
V = 1058.3 (3) Å³	0.30 × 0.25 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	6146 independent reflections
Radiation source: fine-focus sealed tube	5186 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −16→16
T_min = 0.388, T_max = 0.442	k = −12→11
13846 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0665P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
6146 reflections	Δρ_max = 1.97 e Å⁻³
289 parameters	Δρ_min = −0.86 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2866 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.025 (11)

Crystal data top

C₁₀H₈BrF₃N₂	V = 1058.3 (3) Å³
M_r = 293.09	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 11.642 (2) Å	µ = 3.90 mm⁻¹
b = 8.5455 (16) Å	T = 120 K
c = 11.846 (2) Å	0.30 × 0.25 × 0.25 mm
β = 116.106 (3)°

Data collection top

Bruker APEXII CCD diffractometer	6146 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	5186 reflections with I > 2σ(I)
T_min = 0.388, T_max = 0.442	R_int = 0.043
13846 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.118	Δρ_max = 1.97 e Å⁻³
S = 1.01	Δρ_min = −0.86 e Å⁻³
6146 reflections	Absolute structure: Flack (1983), 2866 Friedel pairs
289 parameters	Absolute structure parameter: 0.025 (11)
1 restraint

Special details top

Geometry. 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.11522 (3)	0.26312 (4)	1.18963 (3)	0.03080 (7)
F1	0.09963 (18)	0.2247 (3)	0.45774 (18)	0.0409 (5)
F2	−0.0174 (2)	0.4285 (3)	0.3927 (2)	0.0451 (5)
F3	−0.1028 (2)	0.2017 (3)	0.35005 (19)	0.0444 (6)
N1	0.0732 (2)	0.2970 (3)	0.6606 (2)	0.0273 (6)
N2	−0.1541 (2)	0.2779 (3)	0.5405 (2)	0.0275 (5)
C1	−0.0288 (3)	0.2907 (3)	0.5599 (3)	0.0251 (6)
C2	−0.0130 (3)	0.2852 (4)	0.4393 (3)	0.0295 (7)
C3	−0.2122 (3)	0.3864 (4)	0.5954 (3)	0.0319 (7)
H3A	−0.1607	0.4771	0.6428	0.038*
H3B	−0.2703	0.3426	0.6283	0.038*
C4	−0.2560 (3)	0.3829 (4)	0.4556 (3)	0.0345 (8)
H4A	−0.3408	0.3367	0.4024	0.041*
H4B	−0.2311	0.4713	0.4170	0.041*
C5	0.0744 (3)	0.2934 (4)	0.7808 (3)	0.0255 (6)
C6	−0.0055 (3)	0.1941 (4)	0.8088 (3)	0.0283 (7)
H6	−0.0683	0.1327	0.7443	0.034*
C7	0.0070 (3)	0.1857 (4)	0.9306 (3)	0.0285 (7)
H7	−0.0466	0.1183	0.9502	0.034*
C8	0.0988 (2)	0.2770 (4)	1.0237 (3)	0.0267 (6)
C9	0.1785 (3)	0.3738 (4)	0.9972 (3)	0.0274 (6)
H9	0.2406	0.4358	1.0619	0.033*
C10	0.1679 (3)	0.3806 (4)	0.8765 (3)	0.0279 (7)
H10	0.2245	0.4448	0.8587	0.034*
Br2	0.42565 (3)	0.56843 (4)	0.34093 (3)	0.03331 (7)
F4	0.6460 (2)	0.5903 (4)	1.18097 (19)	0.0506 (6)
F5	0.44343 (19)	0.6038 (3)	1.07301 (19)	0.0455 (6)
F6	0.5344 (2)	0.3820 (3)	1.1287 (2)	0.0497 (6)
N3	0.4603 (2)	0.5260 (3)	0.8663 (2)	0.0261 (6)
N4	0.6881 (2)	0.5003 (3)	0.9894 (2)	0.0273 (6)
C11	0.5624 (3)	0.5129 (4)	0.9676 (3)	0.0241 (6)
C12	0.5469 (3)	0.5233 (4)	1.0885 (3)	0.0293 (7)
C13	0.7334 (3)	0.3884 (4)	0.9255 (3)	0.0320 (7)
H13A	0.7994	0.4238	0.8999	0.038*
H13B	0.6710	0.3124	0.8677	0.038*
C14	0.7710 (3)	0.3724 (4)	1.0628 (3)	0.0342 (8)
H14A	0.7318	0.2866	1.0901	0.041*
H14B	0.8603	0.3982	1.1222	0.041*
C15	0.4617 (3)	0.5305 (3)	0.7482 (3)	0.0242 (6)
C16	0.5513 (3)	0.6135 (4)	0.7248 (3)	0.0284 (7)
H16	0.6205	0.6634	0.7923	0.034*
C17	0.5408 (3)	0.6246 (4)	0.6031 (3)	0.0283 (7)
H17	0.6023	0.6813	0.5872	0.034*
C18	0.4399 (3)	0.5519 (4)	0.5065 (3)	0.0263 (6)
C19	0.3487 (3)	0.4687 (4)	0.5270 (3)	0.0294 (7)
H19	0.2802	0.4184	0.4592	0.035*
C20	0.3586 (3)	0.4601 (4)	0.6479 (3)	0.0280 (7)
H20	0.2952	0.4061	0.6627	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02611 (10)	0.03998 (15)	0.02471 (11)	0.00583 (12)	0.00971 (9)	0.00366 (12)
F1	0.0358 (8)	0.0569 (14)	0.0337 (8)	0.0102 (8)	0.0188 (7)	0.0010 (8)
F2	0.0660 (11)	0.0346 (11)	0.0429 (9)	0.0019 (9)	0.0315 (9)	0.0065 (8)
F3	0.0423 (10)	0.0577 (13)	0.0293 (8)	−0.0130 (10)	0.0122 (8)	−0.0137 (9)
N1	0.0243 (9)	0.0302 (13)	0.0260 (10)	−0.0010 (9)	0.0099 (8)	−0.0010 (9)
N2	0.0209 (9)	0.0305 (12)	0.0267 (10)	−0.0031 (10)	0.0066 (8)	−0.0002 (10)
C1	0.0245 (10)	0.0251 (14)	0.0239 (11)	−0.0043 (10)	0.0088 (9)	−0.0046 (10)
C2	0.0301 (12)	0.0265 (15)	0.0278 (12)	−0.0035 (11)	0.0090 (10)	−0.0042 (11)
C3	0.0260 (12)	0.0347 (16)	0.0347 (14)	0.0017 (12)	0.0130 (11)	−0.0019 (12)
C4	0.0251 (12)	0.0389 (17)	0.0343 (14)	0.0007 (13)	0.0082 (11)	0.0002 (13)
C5	0.0211 (10)	0.0302 (15)	0.0234 (11)	0.0010 (10)	0.0082 (9)	0.0009 (10)
C6	0.0250 (12)	0.0275 (14)	0.0305 (13)	−0.0021 (11)	0.0104 (10)	−0.0007 (11)
C7	0.0291 (12)	0.0238 (14)	0.0307 (13)	−0.0041 (11)	0.0112 (11)	0.0021 (11)
C8	0.0255 (10)	0.0297 (14)	0.0276 (11)	0.0030 (12)	0.0143 (9)	0.0019 (11)
C9	0.0192 (11)	0.0283 (14)	0.0300 (13)	−0.0010 (10)	0.0064 (10)	−0.0046 (11)
C10	0.0201 (10)	0.0293 (14)	0.0321 (13)	−0.0019 (11)	0.0093 (10)	0.0018 (12)
Br2	0.03588 (13)	0.03795 (15)	0.02514 (11)	0.00254 (13)	0.01254 (10)	0.00202 (12)
F4	0.0362 (9)	0.0816 (18)	0.0296 (8)	−0.0126 (11)	0.0106 (7)	−0.0142 (11)
F5	0.0434 (9)	0.0601 (15)	0.0381 (9)	0.0166 (10)	0.0227 (8)	0.0032 (9)
F6	0.0759 (12)	0.0382 (11)	0.0497 (10)	0.0016 (11)	0.0411 (9)	0.0083 (9)
N3	0.0213 (9)	0.0281 (13)	0.0247 (10)	−0.0008 (9)	0.0064 (8)	0.0010 (9)
N4	0.0192 (9)	0.0300 (12)	0.0285 (11)	0.0033 (9)	0.0067 (9)	0.0002 (10)
C11	0.0231 (11)	0.0207 (12)	0.0267 (12)	−0.0004 (10)	0.0093 (10)	−0.0006 (10)
C12	0.0237 (12)	0.0372 (16)	0.0232 (12)	0.0025 (11)	0.0068 (10)	−0.0014 (11)
C13	0.0301 (12)	0.0297 (15)	0.0361 (14)	0.0028 (12)	0.0144 (11)	−0.0051 (12)
C14	0.0228 (12)	0.0367 (16)	0.0347 (15)	0.0057 (12)	0.0049 (11)	0.0074 (13)
C15	0.0184 (10)	0.0257 (14)	0.0260 (11)	0.0019 (9)	0.0073 (9)	0.0011 (10)
C16	0.0234 (11)	0.0303 (15)	0.0285 (12)	−0.0025 (10)	0.0088 (10)	−0.0019 (11)
C17	0.0232 (11)	0.0294 (14)	0.0301 (13)	0.0018 (11)	0.0095 (10)	0.0076 (11)
C18	0.0234 (11)	0.0309 (15)	0.0221 (11)	0.0038 (11)	0.0077 (9)	0.0029 (11)
C19	0.0215 (11)	0.0363 (16)	0.0274 (12)	−0.0006 (11)	0.0080 (10)	−0.0029 (12)
C20	0.0186 (10)	0.0313 (14)	0.0302 (13)	−0.0033 (11)	0.0073 (10)	−0.0033 (12)

Geometric parameters (Å, º) top

Br1—C8	1.893 (3)	Br2—C18	1.899 (3)
F1—C2	1.335 (4)	F4—C12	1.322 (4)
F2—C2	1.335 (4)	F5—C12	1.328 (4)
F3—C2	1.322 (4)	F6—C12	1.329 (4)
N1—C1	1.261 (3)	N3—C11	1.269 (4)
N1—C5	1.418 (4)	N3—C15	1.407 (4)
N2—C1	1.377 (4)	N4—C11	1.373 (4)
N2—C3	1.459 (4)	N4—C13	1.456 (4)
N2—C4	1.474 (4)	N4—C14	1.464 (4)
C1—C2	1.520 (4)	C11—C12	1.522 (5)
C3—C4	1.504 (5)	C13—C14	1.493 (5)
C3—H3A	0.9900	C13—H13A	0.9900
C3—H3B	0.9900	C13—H13B	0.9900
C4—H4A	0.9900	C14—H14A	0.9900
C4—H4B	0.9900	C14—H14B	0.9900
C5—C10	1.392 (4)	C15—C16	1.387 (4)
C5—C6	1.403 (5)	C15—C20	1.399 (4)
C6—C7	1.387 (5)	C16—C17	1.396 (5)
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.389 (4)	C17—C18	1.375 (4)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.378 (4)	C18—C19	1.386 (5)
C9—C10	1.382 (4)	C19—C20	1.387 (5)
C9—H9	0.9500	C19—H19	0.9500
C10—H10	0.9500	C20—H20	0.9500

C1—N1—C5	122.5 (3)	C11—N3—C15	121.8 (3)
C1—N2—C3	122.7 (3)	C11—N4—C13	123.6 (3)
C1—N2—C4	122.7 (3)	C11—N4—C14	122.7 (3)
C3—N2—C4	61.7 (2)	C13—N4—C14	61.5 (2)
N1—C1—N2	130.5 (3)	N3—C11—N4	131.5 (3)
N1—C1—C2	115.9 (3)	N3—C11—C12	115.8 (3)
N2—C1—C2	113.4 (2)	N4—C11—C12	112.6 (2)
F3—C2—F2	107.0 (2)	F4—C12—F5	107.3 (3)
F3—C2—F1	107.2 (3)	F4—C12—F6	106.8 (3)
F2—C2—F1	106.2 (3)	F5—C12—F6	106.5 (3)
F3—C2—C1	112.8 (3)	F4—C12—C11	112.6 (3)
F2—C2—C1	111.2 (3)	F5—C12—C11	112.1 (2)
F1—C2—C1	112.0 (2)	F6—C12—C11	111.2 (3)
N2—C3—C4	59.7 (2)	N4—C13—C14	59.5 (2)
N2—C3—H3A	117.8	N4—C13—H13A	117.8
C4—C3—H3A	117.8	C14—C13—H13A	117.8
N2—C3—H3B	117.8	N4—C13—H13B	117.8
C4—C3—H3B	117.8	C14—C13—H13B	117.8
H3A—C3—H3B	114.9	H13A—C13—H13B	115.0
N2—C4—C3	58.6 (2)	N4—C14—C13	59.0 (2)
N2—C4—H4A	117.9	N4—C14—H14A	117.9
C3—C4—H4A	117.9	C13—C14—H14A	117.9
N2—C4—H4B	117.9	N4—C14—H14B	117.9
C3—C4—H4B	117.9	C13—C14—H14B	117.9
H4A—C4—H4B	115.1	H14A—C14—H14B	115.0
C10—C5—C6	119.6 (3)	C16—C15—C20	119.3 (3)
C10—C5—N1	117.7 (3)	C16—C15—N3	123.4 (3)
C6—C5—N1	122.4 (3)	C20—C15—N3	116.9 (3)
C7—C6—C5	120.0 (3)	C15—C16—C17	120.6 (3)
C7—C6—H6	120.0	C15—C16—H16	119.7
C5—C6—H6	120.0	C17—C16—H16	119.7
C6—C7—C8	119.3 (3)	C18—C17—C16	118.9 (3)
C6—C7—H7	120.4	C18—C17—H17	120.5
C8—C7—H7	120.4	C16—C17—H17	120.5
C9—C8—C7	121.1 (3)	C17—C18—C19	121.7 (3)
C9—C8—Br1	120.2 (2)	C17—C18—Br2	118.7 (2)
C7—C8—Br1	118.7 (2)	C19—C18—Br2	119.6 (2)
C8—C9—C10	119.9 (3)	C18—C19—C20	119.1 (3)
C8—C9—H9	120.1	C18—C19—H19	120.5
C10—C9—H9	120.1	C20—C19—H19	120.5
C9—C10—C5	120.2 (3)	C19—C20—C15	120.3 (3)
C9—C10—H10	119.9	C19—C20—H20	119.9
C5—C10—H10	119.9	C15—C20—H20	119.9

C5—N1—C1—N2	−0.8 (5)	C15—N3—C11—N4	−0.2 (5)
C5—N1—C1—C2	−176.2 (3)	C15—N3—C11—C12	175.1 (3)
C3—N2—C1—N1	54.6 (5)	C13—N4—C11—N3	−50.5 (5)
C4—N2—C1—N1	129.6 (4)	C14—N4—C11—N3	−125.8 (4)
C3—N2—C1—C2	−130.0 (3)	C13—N4—C11—C12	134.1 (3)
C4—N2—C1—C2	−54.9 (4)	C14—N4—C11—C12	58.8 (4)
N1—C1—C2—F3	146.9 (3)	N3—C11—C12—F4	−146.2 (3)
N2—C1—C2—F3	−29.3 (4)	N4—C11—C12—F4	30.0 (4)
N1—C1—C2—F2	−92.9 (3)	N3—C11—C12—F5	−25.1 (4)
N2—C1—C2—F2	91.0 (3)	N4—C11—C12—F5	151.1 (3)
N1—C1—C2—F1	25.8 (4)	N3—C11—C12—F6	94.0 (3)
N2—C1—C2—F1	−150.3 (3)	N4—C11—C12—F6	−89.9 (3)
C1—N2—C3—C4	112.6 (3)	C11—N4—C13—C14	−112.2 (3)
C1—N2—C4—C3	−112.5 (3)	C11—N4—C14—C13	113.6 (3)
C1—N1—C5—C10	−145.7 (3)	C11—N3—C15—C16	−41.6 (4)
C1—N1—C5—C6	40.9 (4)	C11—N3—C15—C20	145.2 (3)
C10—C5—C6—C7	1.3 (5)	C20—C15—C16—C17	−1.3 (5)
N1—C5—C6—C7	174.6 (3)	N3—C15—C16—C17	−174.3 (3)
C5—C6—C7—C8	0.3 (5)	C15—C16—C17—C18	0.1 (5)
C6—C7—C8—C9	−0.9 (5)	C16—C17—C18—C19	0.2 (5)
C6—C7—C8—Br1	−179.6 (2)	C16—C17—C18—Br2	179.6 (2)
C7—C8—C9—C10	−0.2 (5)	C17—C18—C19—C20	0.7 (5)
Br1—C8—C9—C10	178.5 (2)	Br2—C18—C19—C20	−178.7 (2)
C8—C9—C10—C5	1.9 (5)	C18—C19—C20—C15	−1.9 (5)
C6—C5—C10—C9	−2.5 (5)	C16—C15—C20—C19	2.2 (5)
N1—C5—C10—C9	−176.0 (3)	N3—C15—C20—C19	175.7 (3)

Experimental details

Crystal data
Chemical formula	C₁₀H₈BrF₃N₂
M_r	293.09
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	120
a, b, c (Å)	11.642 (2), 8.5455 (16), 11.846 (2)
β (°)	116.106 (3)
V (Å³)	1058.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.90
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.388, 0.442
No. of measured, independent and observed [I > 2σ(I)] reflections	13846, 6146, 5186
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.118, 1.01
No. of reflections	6146
No. of parameters	289
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.97, −0.86
Absolute structure	Flack (1983), 2866 Friedel pairs
Absolute structure parameter	0.025 (11)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the Ministry of Education and Science of the Russian Federation (State contract No. 426).

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