(Z)-N-[1-(Aziridin-1-yl)-2,2,2-tri-fluoro-ethyl-idene]-4-bromo-aniline.

The title compound, C10H8BrF3N2, crystallizes with two independent mol-ecules 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, mol-ecules related by translation in [001] inter-act through short inter-molecular Br⋯F contacts [3.276 (2) and 3.284 (2) Å], thus forming two types of crystallographically independent chains.

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 = 293.09

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.118

S = 1.01

6146 reflections

289 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.97 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814007867/cv5449sup1.cif

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

Click here for additional data file.

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

CCDC reference: 996162

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H8BrF3N2	F(000) = 576
Mr = 293.09	Dx = 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

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

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(Fo2) + (0.0665P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
6146 reflections	Δρmax = 1.97 e Å−3
289 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)