4-(2,6-Dibromo-4-fluoro-anilino)pent-3-en-2-one.

The title enamino-ketone, C(11)H(10)Br(2)FNO, has a roughly planar pentenone chain; the maximum displacement of an atom from the pentenone plane is 0.071 (4) Å. The dihedral angle between the benzene ring and the pentenone unit is 77.2 (1)°. Inter-molecular C-H⋯Br and C-H⋯O inter-actions, as well as an intra-molecular N-H⋯O inter-action, are observed. In both methyl groups, each H atom is disordered equally over two sites.

Related literature

For synthetic background, see: Shaheen et al. (2006 ▶); Venter et al. (2010a ▶,b ▶). For applications of enamino­ketones, see: Brink et al. (2010 ▶); Chen & Rhodes (1996 ▶); Nair et al. (2002 ▶); Otto et al. (1998 ▶); Pyżuk et al. (1993 ▶); Roodt & Steyn (2000 ▶); Steyn et al. (1992 ▶, 1997 ▶); Tan et al. (2008 ▶); Van Aswegen et al. (1991 ▶); Xia et al. (2008 ▶). For related ligand systems, see: Venter et al. (2009a ▶,b ▶).

Experimental

Crystal data

C11H10Br2FNO

M = 351.02

Orthorhombic,

a = 8.7710 (3) Å

b = 10.8710 (4) Å

c = 12.6720 (4) Å

V = 1208.27 (7) Å3

Z = 4

Mo Kα radiation

μ = 6.70 mm−1

T = 100 K

0.66 × 0.25 × 0.18 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.096, T max = 0.379

20084 measured reflections

2624 independent reflections

2381 reflections with I > 2σ(I)

R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.063

S = 1.04

2624 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.70 e Å−3

Absolute structure: Flack (1983 ▶), 1102 Friedel pairs

Flack parameter: 0.057 (12)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044606/wn2454sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044606/wn2454Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044606/wn2454Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H10Br2FNO	F(000) = 680
Mr = 351.02	Dx = 1.93 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9975 reflections
a = 8.7710 (3) Å	θ = 2.5–26.8°
b = 10.8710 (4) Å	µ = 6.70 mm−1
c = 12.6720 (4) Å	T = 100 K
V = 1208.27 (7) Å3	Cuboid, colourless
Z = 4	0.66 × 0.25 × 0.18 mm

Bruker X8 APEXII 4K KappaCCD diffractometer	2624 independent reflections
Radiation source: fine-focus sealed tube	2381 reflections with I > 2σ(I)
graphite	Rint = 0.084
ω and φ scans	θmax = 27°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.096, Tmax = 0.379	k = −13→13
20084 measured reflections	l = −15→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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.0221P)2 + 0.0721P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2624 reflections	Δρmax = 0.48 e Å−3
147 parameters	Δρmin = −0.70 e Å−3
0 restraints	Absolute structure: Flack (1983), 1102 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.057 (12)

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 5 s/frame. A total of 1849 frames were collected with a frame width of 0.5° covering up to θ = 26.83° with 99.9% completeness accomplished.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.3941 (5)	0.1897 (4)	0.4390 (3)	0.0321 (9)
H1A	0.4724	0.2509	0.4559	0.048*	0.5
H1B	0.4397	0.123	0.3975	0.048*	0.5
H1C	0.3517	0.1561	0.5045	0.048*	0.5
H1D	0.3702	0.1025	0.4494	0.048*	0.5
H1E	0.4028	0.2303	0.5077	0.048*	0.5
H1F	0.4908	0.1973	0.4008	0.048*	0.5
C2	0.2691 (4)	0.2495 (3)	0.3761 (3)	0.0205 (8)
C3	0.1464 (4)	0.1850 (3)	0.3420 (3)	0.0193 (8)
H3	0.1393	0.101	0.3621	0.023*
C4	0.0266 (4)	0.2343 (3)	0.2780 (2)	0.0176 (8)
C5	−0.0933 (4)	0.1488 (3)	0.2389 (3)	0.0284 (9)
H5A	−0.1672	0.1947	0.1964	0.043*	0.5
H5B	−0.1454	0.1109	0.2991	0.043*	0.5
H5C	−0.0461	0.0846	0.1956	0.043*	0.5
H5D	−0.0719	0.0654	0.2643	0.043*	0.5
H5E	−0.0937	0.1492	0.1616	0.043*	0.5
H5F	−0.1931	0.1755	0.2651	0.043*	0.5
C111	0.4145 (4)	0.4411 (3)	0.3773 (3)	0.0177 (7)
C112	0.4141 (4)	0.5250 (3)	0.4607 (3)	0.0183 (7)
C113	0.5425 (4)	0.5915 (3)	0.4879 (3)	0.0213 (8)
H113	0.5406	0.6487	0.5446	0.026*
C114	0.6730 (4)	0.5723 (3)	0.4304 (3)	0.0232 (8)
C115	0.6803 (4)	0.4939 (3)	0.3454 (3)	0.0222 (8)
H115	0.7719	0.4836	0.3063	0.027*
C116	0.5489 (4)	0.4306 (3)	0.3194 (2)	0.0202 (7)
N11	0.2846 (3)	0.3703 (2)	0.3530 (2)	0.0198 (7)
H11	0.212	0.4057	0.3220	0.03*
O12	0.0192 (3)	0.3462 (2)	0.2553 (2)	0.0236 (6)
F14	0.8008 (2)	0.6351 (2)	0.45685 (18)	0.0322 (5)
Br12	0.23441 (4)	0.54808 (3)	0.53970 (3)	0.02556 (11)
Br16	0.55267 (5)	0.32820 (4)	0.19895 (3)	0.03091 (12)

	U11	U22	U33	U12	U13	U23
C1	0.038 (2)	0.022 (2)	0.036 (2)	0.0009 (18)	−0.0122 (18)	0.0052 (18)
C2	0.029 (2)	0.0168 (17)	0.0156 (16)	0.0030 (16)	0.0038 (16)	−0.0017 (14)
C3	0.025 (2)	0.0096 (16)	0.0229 (17)	−0.0021 (16)	0.0014 (15)	0.0040 (15)
C4	0.018 (2)	0.0175 (18)	0.0176 (17)	0.0005 (15)	0.0070 (14)	−0.0024 (14)
C5	0.019 (2)	0.022 (2)	0.045 (2)	−0.0041 (16)	−0.0055 (17)	0.0049 (18)
C111	0.0196 (19)	0.0122 (16)	0.0211 (17)	0.0013 (15)	−0.0056 (14)	0.0016 (15)
C112	0.0223 (19)	0.0151 (17)	0.0176 (16)	0.0046 (14)	0.0021 (15)	0.0014 (15)
C113	0.029 (2)	0.0146 (17)	0.0205 (18)	−0.0012 (17)	−0.0043 (16)	0.0017 (14)
C114	0.0225 (19)	0.0178 (19)	0.029 (2)	−0.0069 (16)	−0.0062 (16)	0.0080 (16)
C115	0.0193 (19)	0.026 (2)	0.0210 (17)	0.0021 (16)	−0.0007 (14)	0.0065 (17)
C116	0.0238 (19)	0.0230 (18)	0.0138 (16)	0.0057 (17)	−0.0035 (15)	−0.0019 (14)
N11	0.0189 (16)	0.0144 (14)	0.0262 (15)	0.0003 (12)	−0.0063 (13)	−0.0005 (13)
O12	0.0212 (14)	0.0162 (13)	0.0333 (14)	−0.0001 (11)	−0.0054 (11)	0.0041 (12)
F14	0.0277 (12)	0.0315 (12)	0.0375 (12)	−0.0103 (10)	−0.0077 (10)	−0.0010 (11)
Br12	0.0260 (2)	0.0285 (2)	0.02217 (18)	0.00240 (17)	0.00389 (16)	−0.00038 (16)
Br16	0.0296 (2)	0.0391 (2)	0.02405 (18)	0.0117 (2)	−0.00532 (17)	−0.01234 (18)

C1—C2	1.503 (5)	C5—H5D	0.98
C1—H1A	0.98	C5—H5E	0.98
C1—H1B	0.98	C5—H5F	0.98
C1—H1C	0.98	C111—C116	1.393 (5)
C1—H1D	0.98	C111—C112	1.397 (5)
C1—H1E	0.98	C111—N11	1.408 (4)
C1—H1F	0.98	C112—C113	1.382 (5)
C2—N11	1.353 (4)	C112—Br12	1.884 (3)
C2—C3	1.355 (5)	C113—C114	1.373 (5)
C3—C4	1.431 (5)	C113—H113	0.95
C3—H3	0.95	C114—F14	1.355 (4)
C4—O12	1.252 (4)	C114—C115	1.375 (5)
C4—C5	1.488 (5)	C115—C116	1.382 (5)
C5—H5A	0.98	C115—H115	0.95
C5—H5B	0.98	C116—Br16	1.889 (3)
C5—H5C	0.98	N11—H11	0.8453
C2—C1—H1A	109.5	C4—C5—H5D	109.5
C2—C1—H1B	109.5	H5A—C5—H5D	141.1
H1A—C1—H1B	109.5	H5B—C5—H5D	56.3
C2—C1—H1C	109.5	H5C—C5—H5D	56.3
H1A—C1—H1C	109.5	C4—C5—H5E	109.5
H1B—C1—H1C	109.5	H5A—C5—H5E	56.3
C2—C1—H1D	109.5	H5B—C5—H5E	141.1
H1A—C1—H1D	141.1	H5C—C5—H5E	56.3
H1B—C1—H1D	56.3	H5D—C5—H5E	109.5
H1C—C1—H1D	56.3	C4—C5—H5F	109.5
C2—C1—H1E	109.5	H5A—C5—H5F	56.3
H1A—C1—H1E	56.3	H5B—C5—H5F	56.3
H1B—C1—H1E	141.1	H5C—C5—H5F	141.1
H1C—C1—H1E	56.3	H5D—C5—H5F	109.5
H1D—C1—H1E	109.5	H5E—C5—H5F	109.5
C2—C1—H1F	109.5	C116—C111—C112	117.0 (3)
H1A—C1—H1F	56.3	C116—C111—N11	121.7 (3)
H1B—C1—H1F	56.3	C112—C111—N11	121.3 (3)
H1C—C1—H1F	141.1	C113—C112—C111	121.9 (3)
H1D—C1—H1F	109.5	C113—C112—Br12	118.6 (2)
H1E—C1—H1F	109.5	C111—C112—Br12	119.4 (2)
N11—C2—C3	120.9 (3)	C114—C113—C112	117.8 (3)
N11—C2—C1	117.4 (3)	C114—C113—H113	121.1
C3—C2—C1	121.6 (3)	C112—C113—H113	121.1
C2—C3—C4	124.7 (3)	F14—C114—C113	118.8 (3)
C2—C3—H3	117.6	F14—C114—C115	117.9 (3)
C4—C3—H3	117.6	C113—C114—C115	123.3 (3)
O12—C4—C3	122.2 (3)	C114—C115—C116	117.2 (3)
O12—C4—C5	119.6 (3)	C114—C115—H115	121.4
C3—C4—C5	118.3 (3)	C116—C115—H115	121.4
C4—C5—H5A	109.5	C115—C116—C111	122.7 (3)
C4—C5—H5B	109.5	C115—C116—Br16	118.1 (3)
H5A—C5—H5B	109.5	C111—C116—Br16	119.2 (3)
C4—C5—H5C	109.5	C2—N11—C111	124.4 (3)
H5A—C5—H5C	109.5	C2—N11—H11	117.8
H5B—C5—H5C	109.5	C111—N11—H11	117.8
N11—C2—C3—C4	1.8 (6)	F14—C114—C115—C116	−179.9 (3)
C1—C2—C3—C4	−177.1 (3)	C113—C114—C115—C116	−1.1 (5)
C2—C3—C4—O12	−6.2 (5)	C114—C115—C116—C111	−2.0 (5)
C2—C3—C4—C5	174.5 (3)	C114—C115—C116—Br16	177.0 (3)
C116—C111—C112—C113	−2.5 (5)	C112—C111—C116—C115	3.8 (5)
N11—C111—C112—C113	177.4 (3)	N11—C111—C116—C115	−176.2 (3)
C116—C111—C112—Br12	178.0 (2)	C112—C111—C116—Br16	−175.2 (2)
N11—C111—C112—Br12	−2.1 (4)	N11—C111—C116—Br16	4.8 (4)
C111—C112—C113—C114	−0.4 (5)	C3—C2—N11—C111	−174.1 (3)
Br12—C112—C113—C114	179.2 (3)	C1—C2—N11—C111	4.8 (5)
C112—C113—C114—F14	−178.9 (3)	C116—C111—N11—C2	75.4 (5)
C112—C113—C114—C115	2.3 (5)	C112—C111—N11—C2	−104.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O12	0.85	1.99	2.650 (4)	134.
C5—H5A···Br16i	0.98	2.85	3.702 (4)	145.
C5—H5F···Br16i	0.98	2.90	3.702 (4)	139
C5—H5B···Br12ii	0.98	2.88	3.839 (4)	168.
C5—H5D···O12iii	0.98	2.44	3.354 (4)	155

Parameters	I	II	III	IV
N11—C111	1.409 (4)	1.412 (3)	1.422 (2)	1.417 (2)
N11—C2	1.352 (4)	1.352 (3)	1.345 (2)	1.348 (1)
O12—C4	1.252 (4)	1.244 (3)	1.257 (2)	1.253 (1)
C2—C3	1.355 (5)	1.365 (4)	1.383 (3)	1.384 (2)
C3—C4	1.432 (5)	1.424 (4)	1.420 (2)	1.424 (2)
N11···O12	2.650 (4)	2.658 (3)	2.635 (2)	2.646 (1)
N11—C2···C4—O12	-3.8 (3)	1.4 (2)	-0.5 (1)	1.70 (9)
Dihedral angle	77.2 (1)	32.03 (9)	49.53 (5)	29.90 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H11⋯O12	0.85	1.99	2.650 (4)	134
C5—H5A⋯Br16i	0.98	2.85	3.702 (4)	145
C5—H5F⋯Br16i	0.98	2.90	3.702 (4)	139
C5—H5B⋯Br12ii	0.98	2.88	3.839 (4)	168
C5—H5D⋯O12iii	0.98	2.44	3.354 (4)	155

Symmetry codes: (i) ; (ii) ; (iii) .