2,3-Dibromo-1-(4-chloro-phen-yl)-3-(5-nitro-2-fur-yl)propan-1-one.

In the title compound, C(13)H(8)Br(2)ClNO(4), the linking -CHBr-CHBr- fragment is disordered over two orientations with refined site occupancies of 0.512 (11) and 0.488 (11). The dihedral angle between the furan ring and the phenyl ring is 21.86 (16)°. In the crystal, the mol-ecules are linked into [011] chains by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For applications of nitro­furan derivatives, see: Holla et al. (1986 ▶, 1987 ▶, 1992 ▶). For the synthesis, see: Rai et al. (2008 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H8Br2ClNO4

M = 437.47

Triclinic,

a = 8.4932 (11) Å

b = 9.4501 (12) Å

c = 10.5665 (14) Å

α = 92.731 (2)°

β = 107.000 (2)°

γ = 114.299 (2)°

V = 725.32 (16) Å3

Z = 2

Mo Kα radiation

μ = 5.79 mm−1

T = 100 K

0.28 × 0.18 × 0.10 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.297, T max = 0.587

13696 measured reflections

3856 independent reflections

3398 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.064

S = 1.20

3856 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046829/hb5734sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046829/hb5734Isup2.hkl

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

C13H8Br2ClNO4	Z = 2
Mr = 437.47	F(000) = 424
Triclinic, P1	Dx = 2.003 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4932 (11) Å	Cell parameters from 6344 reflections
b = 9.4501 (12) Å	θ = 2.8–30.1°
c = 10.5665 (14) Å	µ = 5.79 mm−1
α = 92.731 (2)°	T = 100 K
β = 107.000 (2)°	Block, colourless
γ = 114.299 (2)°	0.28 × 0.18 × 0.10 mm
V = 725.32 (16) Å3

Bruker APEXII DUO CCD diffractometer	3856 independent reflections
Radiation source: fine-focus sealed tube	3398 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 29.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.297, Tmax = 0.587	k = −12→12
13696 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.P)2 + 0.7632P] where P = (Fo2 + 2Fc2)/3
3856 reflections	(Δ/σ)max = 0.002
227 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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 > σ(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	Occ. (<1)
Br1A	0.6289 (7)	0.5168 (5)	0.7250 (5)	0.0356 (5)	0.512 (11)
Br2A	0.3194 (8)	0.1148 (6)	0.9250 (8)	0.0268 (7)	0.512 (11)
Br1B	0.3164 (8)	0.1124 (6)	0.9164 (8)	0.0282 (9)	0.488 (11)
Br2B	0.5885 (6)	0.5025 (6)	0.7004 (5)	0.0321 (5)	0.488 (11)
Cl1	−0.35654 (9)	0.23719 (8)	0.24802 (6)	0.02977 (14)
O1	0.2656 (3)	0.4225 (2)	0.86289 (18)	0.0295 (4)
O2	0.6347 (3)	0.1530 (2)	0.76863 (18)	0.0345 (5)
O3	0.8567 (3)	−0.0787 (3)	0.7618 (2)	0.0470 (6)
O4	0.6542 (3)	−0.0476 (3)	0.5983 (2)	0.0393 (5)
N1	0.7574 (3)	−0.0148 (3)	0.7148 (2)	0.0300 (5)
C1	−0.0395 (3)	0.3544 (3)	0.6339 (2)	0.0249 (5)
H1A	−0.0353	0.4008	0.7151	0.030*
C2	−0.1827 (3)	0.3272 (3)	0.5175 (2)	0.0245 (5)
H2A	−0.2771	0.3520	0.5201	0.029*
C3	−0.1840 (3)	0.2625 (3)	0.3966 (2)	0.0239 (5)
C4	−0.0475 (4)	0.2207 (3)	0.3908 (3)	0.0331 (6)
H4A	−0.0507	0.1768	0.3089	0.040*
C5	0.0930 (4)	0.2451 (4)	0.5083 (3)	0.0370 (7)
H5A	0.1844	0.2161	0.5056	0.044*
C6	0.0998 (3)	0.3129 (3)	0.6312 (3)	0.0282 (5)
C7	0.2512 (4)	0.3473 (3)	0.7606 (3)	0.0350 (6)
C8A	0.4124 (8)	0.3173 (8)	0.7467 (6)	0.0243 (15)	0.512 (11)
H8AA	0.3686	0.2261	0.6753	0.029*	0.512 (11)
C8B	0.3687 (8)	0.2509 (8)	0.7864 (6)	0.0206 (14)	0.488 (11)
H8BA	0.3450	0.1875	0.7008	0.025*	0.488 (11)
C9A	0.5118 (8)	0.2949 (8)	0.8801 (5)	0.0231 (16)	0.512 (11)
H9AA	0.5574	0.3905	0.9473	0.028*	0.512 (11)
C9B	0.5707 (8)	0.3651 (8)	0.8459 (6)	0.0217 (15)	0.488 (11)
H9BA	0.5934	0.4294	0.9306	0.026*	0.488 (11)
C10	0.6760 (4)	0.2677 (4)	0.8747 (3)	0.0405 (7)
C11	0.8308 (4)	0.2911 (3)	0.9747 (3)	0.0291 (5)
H11A	0.8863	0.3628	1.0561	0.035*
C12	0.8923 (3)	0.1848 (3)	0.9317 (3)	0.0276 (5)
H12A	0.9958	0.1724	0.9780	0.033*
C13	0.7676 (3)	0.1059 (3)	0.8086 (3)	0.0255 (5)

	U11	U22	U33	U12	U13	U23
Br1A	0.0434 (14)	0.0312 (8)	0.0500 (15)	0.0229 (10)	0.0299 (11)	0.0179 (9)
Br2A	0.0255 (13)	0.0341 (15)	0.0279 (8)	0.0156 (11)	0.0148 (8)	0.0104 (8)
Br1B	0.0261 (13)	0.0214 (13)	0.0353 (17)	0.0091 (9)	0.0099 (8)	0.0066 (8)
Br2B	0.0354 (11)	0.0366 (8)	0.0392 (11)	0.0216 (9)	0.0234 (8)	0.0171 (7)
Cl1	0.0302 (3)	0.0323 (3)	0.0260 (3)	0.0153 (3)	0.0070 (2)	0.0031 (2)
O1	0.0310 (9)	0.0303 (10)	0.0275 (9)	0.0170 (8)	0.0066 (8)	−0.0019 (7)
O2	0.0341 (10)	0.0431 (11)	0.0270 (9)	0.0272 (9)	−0.0004 (8)	−0.0104 (8)
O3	0.0382 (12)	0.0446 (13)	0.0647 (15)	0.0293 (11)	0.0128 (11)	−0.0026 (11)
O4	0.0475 (12)	0.0398 (12)	0.0333 (11)	0.0217 (10)	0.0156 (10)	−0.0021 (9)
N1	0.0277 (11)	0.0272 (11)	0.0409 (13)	0.0138 (9)	0.0180 (10)	0.0027 (10)
C1	0.0273 (12)	0.0260 (12)	0.0254 (12)	0.0142 (10)	0.0118 (10)	0.0017 (10)
C2	0.0235 (12)	0.0278 (13)	0.0265 (12)	0.0141 (10)	0.0105 (10)	0.0043 (10)
C3	0.0196 (11)	0.0223 (12)	0.0260 (12)	0.0073 (9)	0.0062 (9)	0.0012 (9)
C4	0.0289 (13)	0.0387 (15)	0.0301 (13)	0.0174 (12)	0.0067 (11)	−0.0082 (11)
C5	0.0260 (13)	0.0458 (17)	0.0363 (14)	0.0202 (13)	0.0041 (11)	−0.0143 (13)
C6	0.0231 (12)	0.0288 (13)	0.0298 (13)	0.0128 (10)	0.0052 (10)	−0.0066 (10)
C7	0.0273 (13)	0.0362 (15)	0.0372 (14)	0.0185 (12)	0.0017 (11)	−0.0118 (12)
C8A	0.026 (3)	0.025 (3)	0.023 (3)	0.014 (2)	0.008 (2)	0.001 (2)
C8B	0.028 (3)	0.020 (3)	0.017 (2)	0.012 (2)	0.009 (2)	0.003 (2)
C9A	0.022 (3)	0.025 (3)	0.023 (2)	0.012 (2)	0.007 (2)	−0.001 (2)
C9B	0.024 (3)	0.023 (3)	0.025 (3)	0.012 (2)	0.015 (2)	0.007 (2)
C10	0.0381 (16)	0.0500 (18)	0.0316 (14)	0.0307 (15)	−0.0030 (12)	−0.0162 (13)
C11	0.0253 (12)	0.0356 (14)	0.0253 (12)	0.0147 (11)	0.0065 (10)	−0.0004 (10)
C12	0.0227 (12)	0.0318 (14)	0.0314 (13)	0.0133 (11)	0.0114 (10)	0.0083 (11)
C13	0.0248 (12)	0.0267 (12)	0.0323 (13)	0.0153 (10)	0.0141 (10)	0.0064 (10)

Br1A—C8A	2.102 (8)	C5—C6	1.395 (3)
Br2A—C9A	2.008 (9)	C5—H5A	0.9300
Br1B—C8B	1.962 (11)	C6—C7	1.488 (4)
Br2B—C9B	2.059 (8)	C7—C8A	1.553 (5)
Cl1—C3	1.732 (3)	C7—C8B	1.586 (6)
O1—C7	1.211 (3)	C8A—C9A	1.492 (9)
O2—C13	1.343 (3)	C8A—H8AA	0.9800
O2—C10	1.377 (3)	C8B—C9B	1.511 (9)
O3—N1	1.235 (3)	C8B—H8BA	0.9800
O4—N1	1.220 (3)	C9A—C10	1.534 (5)
N1—C13	1.433 (3)	C9A—H9AA	0.9800
C1—C2	1.377 (3)	C9B—C10	1.511 (6)
C1—C6	1.398 (3)	C9B—H9BA	0.9800
C1—H1A	0.9300	C10—C11	1.349 (4)
C2—C3	1.385 (3)	C11—C12	1.420 (3)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.385 (3)	C12—C13	1.349 (4)
C4—C5	1.378 (4)	C12—H12A	0.9300
C4—H4A	0.9300
C13—O2—C10	104.5 (2)	C9B—C8B—C7	109.4 (5)
O4—N1—O3	125.4 (2)	C9B—C8B—Br1B	106.2 (5)
O4—N1—C13	119.5 (2)	C7—C8B—Br1B	112.8 (4)
O3—N1—C13	115.2 (2)	C9B—C8B—H8BA	109.5
C2—C1—C6	120.7 (2)	C7—C8B—H8BA	109.5
C2—C1—H1A	119.6	Br1B—C8B—H8BA	109.5
C6—C1—H1A	119.6	C8A—C9A—C10	110.9 (5)
C1—C2—C3	119.0 (2)	C8A—C9A—Br2A	105.0 (5)
C1—C2—H2A	120.5	C10—C9A—Br2A	114.6 (4)
C3—C2—H2A	120.5	C8A—C9A—H9AA	108.7
C2—C3—C4	121.5 (2)	C10—C9A—H9AA	108.7
C2—C3—Cl1	119.61 (18)	Br2A—C9A—H9AA	108.7
C4—C3—Cl1	118.85 (19)	C10—C9B—C8B	107.3 (5)
C5—C4—C3	119.0 (2)	C10—C9B—Br2B	122.0 (4)
C5—C4—H4A	120.5	C8B—C9B—Br2B	99.1 (4)
C3—C4—H4A	120.5	C10—C9B—H9BA	109.2
C4—C5—C6	120.7 (2)	C8B—C9B—H9BA	109.2
C4—C5—H5A	119.7	Br2B—C9B—H9BA	109.2
C6—C5—H5A	119.7	C11—C10—O2	110.9 (2)
C5—C6—C1	119.0 (2)	C11—C10—C9B	131.8 (3)
C5—C6—C7	123.3 (2)	O2—C10—C9B	115.6 (3)
C1—C6—C7	117.7 (2)	C11—C10—C9A	130.1 (3)
O1—C7—C6	122.1 (2)	O2—C10—C9A	114.4 (3)
O1—C7—C8A	121.7 (3)	C9B—C10—C9A	31.3 (2)
C6—C7—C8A	114.6 (3)	C10—C11—C12	106.6 (2)
O1—C7—C8B	113.5 (3)	C10—C11—H11A	126.7
C6—C7—C8B	122.3 (3)	C12—C11—H11A	126.7
C8A—C7—C8B	29.3 (2)	C13—C12—C11	104.8 (2)
C9A—C8A—C7	108.0 (5)	C13—C12—H12A	127.6
C9A—C8A—Br1A	99.1 (4)	C11—C12—H12A	127.6
C7—C8A—Br1A	114.4 (4)	O2—C13—C12	113.2 (2)
C9A—C8A—H8AA	111.6	O2—C13—N1	116.0 (2)
C7—C8A—H8AA	111.6	C12—C13—N1	130.8 (2)
Br1A—C8A—H8AA	111.6
C6—C1—C2—C3	−2.0 (4)	C7—C8B—C9B—C10	177.3 (3)
C1—C2—C3—C4	1.8 (4)	Br1B—C8B—C9B—C10	55.3 (5)
C1—C2—C3—Cl1	−176.6 (2)	C7—C8B—C9B—Br2B	−54.9 (5)
C2—C3—C4—C5	−0.4 (4)	Br1B—C8B—C9B—Br2B	−176.9 (3)
Cl1—C3—C4—C5	178.1 (2)	C13—O2—C10—C11	1.0 (4)
C3—C4—C5—C6	−0.9 (5)	C13—O2—C10—C9B	168.0 (4)
C4—C5—C6—C1	0.7 (5)	C13—O2—C10—C9A	−157.4 (4)
C4—C5—C6—C7	−177.8 (3)	C8B—C9B—C10—C11	−144.5 (5)
C2—C1—C6—C5	0.8 (4)	Br2B—C9B—C10—C11	102.5 (5)
C2—C1—C6—C7	179.4 (3)	C8B—C9B—C10—O2	51.9 (6)
C5—C6—C7—O1	171.3 (3)	Br2B—C9B—C10—O2	−61.1 (6)
C1—C6—C7—O1	−7.3 (5)	C8B—C9B—C10—C9A	−43.5 (6)
C5—C6—C7—C8A	5.8 (5)	Br2B—C9B—C10—C9A	−156.5 (8)
C1—C6—C7—C8A	−172.8 (4)	C8A—C9A—C10—C11	156.7 (5)
C5—C6—C7—C8B	−26.5 (6)	Br2A—C9A—C10—C11	−84.6 (5)
C1—C6—C7—C8B	154.9 (4)	C8A—C9A—C10—O2	−50.1 (7)
O1—C7—C8A—C9A	36.2 (7)	Br2A—C9A—C10—O2	68.6 (5)
C6—C7—C8A—C9A	−158.2 (4)	C8A—C9A—C10—C9B	49.6 (6)
C8B—C7—C8A—C9A	−45.6 (6)	Br2A—C9A—C10—C9B	168.2 (7)
O1—C7—C8A—Br1A	−73.0 (6)	O2—C10—C11—C12	−0.5 (4)
C6—C7—C8A—Br1A	92.5 (4)	C9B—C10—C11—C12	−164.7 (5)
C8B—C7—C8A—Br1A	−154.8 (7)	C9A—C10—C11—C12	153.5 (5)
O1—C7—C8B—C9B	−63.8 (6)	C10—C11—C12—C13	−0.2 (3)
C6—C7—C8B—C9B	132.7 (4)	C10—O2—C13—C12	−1.1 (3)
C8A—C7—C8B—C9B	49.6 (6)	C10—O2—C13—N1	−179.8 (3)
O1—C7—C8B—Br1B	54.2 (5)	C11—C12—C13—O2	0.9 (3)
C6—C7—C8B—Br1B	−109.4 (4)	C11—C12—C13—N1	179.3 (3)
C8A—C7—C8B—Br1B	167.5 (7)	O4—N1—C13—O2	13.2 (4)
C7—C8A—C9A—C10	−178.9 (4)	O3—N1—C13—O2	−166.3 (2)
Br1A—C8A—C9A—C10	−59.4 (5)	O4—N1—C13—C12	−165.2 (3)
C7—C8A—C9A—Br2A	56.7 (5)	O3—N1—C13—C12	15.3 (4)
Br1A—C8A—C9A—Br2A	176.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9A—H9AA···O1i	0.98	2.26	3.199 (6)	160
C4—H4A···O3ii	0.93	2.46	3.184 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9A—H9AA⋯O1i	0.98	2.26	3.199 (6)	160
C4—H4A⋯O3ii	0.93	2.46	3.184 (4)	135

Symmetry codes: (i) ; (ii) .