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

In the title compound, C(13)H(8)Br(2)N(2)O(6), the 2-furyl ring is essentially planar, with a maximum deviation of 0.002 (2) Å. It is inclined at an angle of 33.94 (9)° to the benzene ring. Both nitro groups are slightly twisted away from their attached rings; the dihedral angles are 4.6 (2)° between the nitro group and the 2-furyl ring, and 13.72 (19)° between the nitro group and the benzene ring. In the crystal, mol-ecules are linked into chains along [110] and [10] via two pairs of inter-molecular C-H⋯O hydrogen bonds, displaying R(2) (2)(10) ring motifs.

Related literature

For general background to and the biological activity of nitro­furans, see: Holla et al. (1986 ▶, 1987 ▶, 1992 ▶). For the preparation of title compound, see: Rai et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C13H8Br2N2O6

M = 448.03

Monoclinic,

a = 12.1902 (2) Å

b = 12.2006 (2) Å

c = 9.9761 (2) Å

β = 96.282 (1)°

V = 1474.81 (5) Å3

Z = 4

Mo Kα radiation

μ = 5.53 mm−1

T = 100 K

0.48 × 0.36 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.176, T max = 0.291

22940 measured reflections

5315 independent reflections

4546 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.066

S = 1.02

5315 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.47 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/S1600536810044971/fj2362sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044971/fj2362Isup2.hkl

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

C13H8Br2N2O6	F(000) = 872
Mr = 448.03	Dx = 2.018 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9181 reflections
a = 12.1902 (2) Å	θ = 2.7–35.0°
b = 12.2006 (2) Å	µ = 5.53 mm−1
c = 9.9761 (2) Å	T = 100 K
β = 96.282 (1)°	Block, light yellow
V = 1474.81 (5) Å3	0.48 × 0.36 × 0.30 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5315 independent reflections
Radiation source: fine-focus sealed tube	4546 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 32.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→17
Tmin = 0.176, Tmax = 0.291	k = −18→18
22940 measured reflections	l = −15→15

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0329P)2 + 0.6835P] where P = (Fo2 + 2Fc2)/3
5315 reflections	(Δ/σ)max = 0.003
208 parameters	Δρmax = 0.84 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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

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	1.041889 (15)	0.421114 (15)	0.681600 (19)	0.03228 (5)
Br2	0.885347 (14)	0.105613 (13)	0.491276 (17)	0.02690 (5)
O1	1.09576 (10)	0.14526 (11)	0.72205 (13)	0.0308 (3)
O2	0.79177 (9)	0.35369 (9)	0.44313 (11)	0.0231 (2)
O3	0.57672 (11)	0.52110 (12)	0.31188 (15)	0.0376 (3)
O4	0.71217 (11)	0.44726 (12)	0.21746 (13)	0.0343 (3)
O5	1.58062 (10)	0.13853 (11)	0.42438 (14)	0.0334 (3)
O6	1.51706 (11)	0.26900 (12)	0.29087 (14)	0.0335 (3)
N1	0.66040 (12)	0.46327 (12)	0.31406 (15)	0.0274 (3)
N2	1.50858 (11)	0.20428 (12)	0.38341 (14)	0.0251 (3)
C1	1.28637 (13)	0.12333 (13)	0.59042 (16)	0.0235 (3)
H1A	1.2691	0.0664	0.6464	0.028*
C2	1.38425 (14)	0.12046 (13)	0.53263 (17)	0.0246 (3)
H2A	1.4337	0.0628	0.5493	0.030*
C3	1.40608 (12)	0.20650 (13)	0.44904 (16)	0.0219 (3)
C4	1.33605 (14)	0.29473 (13)	0.42338 (17)	0.0253 (3)
H4A	1.3540	0.3515	0.3676	0.030*
C5	1.23848 (14)	0.29687 (13)	0.48241 (16)	0.0252 (3)
H5A	1.1900	0.3555	0.4665	0.030*
C6	1.21302 (13)	0.21085 (13)	0.56577 (15)	0.0218 (3)
C7	1.10791 (13)	0.20769 (14)	0.62976 (16)	0.0239 (3)
C8	1.01418 (13)	0.28532 (13)	0.57771 (16)	0.0227 (3)
H8A	1.0158	0.2995	0.4812	0.027*
C9	0.90304 (13)	0.23822 (13)	0.60376 (16)	0.0222 (3)
H9A	0.9064	0.2168	0.6988	0.027*
C10	0.80678 (13)	0.31058 (13)	0.57093 (15)	0.0222 (3)
C11	0.72425 (13)	0.34199 (13)	0.64346 (16)	0.0245 (3)
H11A	0.7166	0.3234	0.7324	0.029*
C12	0.65187 (14)	0.40878 (14)	0.55717 (17)	0.0258 (3)
H12A	0.5873	0.4425	0.5773	0.031*
C13	0.69716 (13)	0.41271 (13)	0.43947 (16)	0.0233 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.03186 (10)	0.03185 (9)	0.03482 (10)	−0.00803 (6)	0.01125 (7)	−0.01036 (7)
Br2	0.02422 (8)	0.02524 (8)	0.03086 (9)	0.00128 (5)	0.00126 (6)	−0.00446 (6)
O1	0.0231 (6)	0.0417 (7)	0.0277 (6)	−0.0014 (5)	0.0023 (5)	0.0128 (5)
O2	0.0209 (5)	0.0286 (5)	0.0210 (5)	0.0039 (4)	0.0068 (4)	0.0037 (4)
O3	0.0334 (7)	0.0421 (7)	0.0381 (7)	0.0164 (6)	0.0073 (6)	0.0102 (6)
O4	0.0344 (7)	0.0457 (7)	0.0241 (6)	0.0072 (6)	0.0086 (5)	0.0075 (5)
O5	0.0231 (6)	0.0371 (6)	0.0404 (7)	0.0058 (5)	0.0059 (5)	0.0039 (5)
O6	0.0285 (6)	0.0407 (7)	0.0329 (6)	0.0017 (5)	0.0104 (5)	0.0080 (5)
N1	0.0259 (7)	0.0302 (7)	0.0265 (7)	0.0032 (5)	0.0049 (5)	0.0045 (5)
N2	0.0208 (6)	0.0291 (6)	0.0255 (6)	−0.0010 (5)	0.0034 (5)	−0.0026 (5)
C1	0.0233 (7)	0.0232 (6)	0.0238 (7)	−0.0010 (5)	0.0013 (6)	0.0015 (5)
C2	0.0238 (7)	0.0234 (7)	0.0265 (7)	0.0020 (5)	0.0026 (6)	0.0003 (6)
C3	0.0193 (6)	0.0252 (7)	0.0215 (7)	−0.0010 (5)	0.0027 (5)	−0.0026 (5)
C4	0.0254 (7)	0.0276 (7)	0.0237 (7)	0.0019 (6)	0.0057 (6)	0.0033 (6)
C5	0.0254 (7)	0.0277 (7)	0.0228 (7)	0.0044 (6)	0.0045 (6)	0.0045 (6)
C6	0.0196 (7)	0.0271 (7)	0.0187 (6)	−0.0002 (5)	0.0019 (5)	0.0009 (5)
C7	0.0204 (7)	0.0302 (7)	0.0207 (7)	−0.0005 (5)	0.0009 (5)	0.0017 (5)
C8	0.0212 (7)	0.0270 (7)	0.0205 (6)	−0.0004 (5)	0.0051 (5)	−0.0008 (5)
C9	0.0202 (7)	0.0256 (7)	0.0212 (7)	0.0007 (5)	0.0037 (5)	−0.0003 (5)
C10	0.0212 (7)	0.0263 (7)	0.0198 (7)	0.0017 (5)	0.0054 (5)	0.0016 (5)
C11	0.0233 (7)	0.0294 (7)	0.0218 (7)	0.0016 (6)	0.0073 (6)	−0.0006 (6)
C12	0.0243 (7)	0.0282 (7)	0.0262 (7)	0.0049 (6)	0.0080 (6)	−0.0013 (6)
C13	0.0217 (7)	0.0251 (7)	0.0238 (7)	0.0038 (5)	0.0054 (5)	0.0015 (5)

Br1—C8	1.9639 (16)	C3—C4	1.380 (2)
Br2—C9	1.9674 (16)	C4—C5	1.384 (2)
O1—C7	1.216 (2)	C4—H4A	0.9300
O2—C13	1.3567 (19)	C5—C6	1.395 (2)
O2—C10	1.3728 (18)	C5—H5A	0.9300
O3—N1	1.2385 (19)	C6—C7	1.493 (2)
O4—N1	1.2240 (19)	C7—C8	1.531 (2)
O5—N2	1.2260 (19)	C8—C9	1.520 (2)
O6—N2	1.2277 (19)	C8—H8A	0.9800
N1—C13	1.423 (2)	C9—C10	1.476 (2)
N2—C3	1.473 (2)	C9—H9A	0.9800
C1—C2	1.381 (2)	C10—C11	1.357 (2)
C1—C6	1.397 (2)	C11—C12	1.420 (2)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.384 (2)	C12—C13	1.352 (2)
C2—H2A	0.9300	C12—H12A	0.9300
C13—O2—C10	104.77 (12)	O1—C7—C8	119.74 (15)
O4—N1—O3	124.87 (15)	C6—C7—C8	118.86 (13)
O4—N1—C13	118.89 (14)	C9—C8—C7	110.75 (13)
O3—N1—C13	116.23 (14)	C9—C8—Br1	109.50 (10)
O5—N2—O6	123.74 (15)	C7—C8—Br1	105.31 (10)
O5—N2—C3	118.38 (14)	C9—C8—H8A	110.4
O6—N2—C3	117.88 (14)	C7—C8—H8A	110.4
C2—C1—C6	120.76 (15)	Br1—C8—H8A	110.4
C2—C1—H1A	119.6	C10—C9—C8	115.96 (13)
C6—C1—H1A	119.6	C10—C9—Br2	109.29 (11)
C1—C2—C3	117.64 (15)	C8—C9—Br2	104.92 (10)
C1—C2—H2A	121.2	C10—C9—H9A	108.8
C3—C2—H2A	121.2	C8—C9—H9A	108.8
C4—C3—C2	123.18 (15)	Br2—C9—H9A	108.8
C4—C3—N2	118.00 (14)	C11—C10—O2	110.84 (13)
C2—C3—N2	118.82 (14)	C11—C10—C9	131.93 (15)
C3—C4—C5	118.60 (15)	O2—C10—C9	117.20 (13)
C3—C4—H4A	120.7	C10—C11—C12	106.65 (14)
C5—C4—H4A	120.7	C10—C11—H11A	126.7
C4—C5—C6	119.81 (15)	C12—C11—H11A	126.7
C4—C5—H5A	120.1	C13—C12—C11	105.13 (14)
C6—C5—H5A	120.1	C13—C12—H12A	127.4
C5—C6—C1	120.00 (15)	C11—C12—H12A	127.4
C5—C6—C7	122.11 (14)	C12—C13—O2	112.62 (14)
C1—C6—C7	117.88 (14)	C12—C13—N1	131.29 (15)
O1—C7—C6	121.40 (15)	O2—C13—N1	116.03 (14)
C6—C1—C2—C3	−0.6 (2)	C7—C8—C9—C10	173.89 (13)
C1—C2—C3—C4	1.2 (2)	Br1—C8—C9—C10	58.18 (16)
C1—C2—C3—N2	−178.53 (14)	C7—C8—C9—Br2	−65.45 (14)
O5—N2—C3—C4	166.33 (15)	Br1—C8—C9—Br2	178.84 (7)
O6—N2—C3—C4	−13.4 (2)	C13—O2—C10—C11	−0.01 (18)
O5—N2—C3—C2	−13.9 (2)	C13—O2—C10—C9	178.03 (14)
O6—N2—C3—C2	166.39 (15)	C8—C9—C10—C11	−128.74 (19)
C2—C3—C4—C5	−0.9 (2)	Br2—C9—C10—C11	112.98 (18)
N2—C3—C4—C5	178.81 (14)	C8—C9—C10—O2	53.73 (19)
C3—C4—C5—C6	0.0 (2)	Br2—C9—C10—O2	−64.55 (16)
C4—C5—C6—C1	0.6 (2)	O2—C10—C11—C12	0.22 (19)
C4—C5—C6—C7	−178.69 (15)	C9—C10—C11—C12	−177.43 (17)
C2—C1—C6—C5	−0.3 (2)	C10—C11—C12—C13	−0.34 (19)
C2—C1—C6—C7	179.02 (15)	C11—C12—C13—O2	0.35 (19)
C5—C6—C7—O1	−165.16 (17)	C11—C12—C13—N1	177.30 (17)
C1—C6—C7—O1	15.6 (2)	C10—O2—C13—C12	−0.22 (18)
C5—C6—C7—C8	14.6 (2)	C10—O2—C13—N1	−177.67 (14)
C1—C6—C7—C8	−164.68 (14)	O4—N1—C13—C12	−173.83 (18)
O1—C7—C8—C9	−26.5 (2)	O3—N1—C13—C12	6.2 (3)
C6—C7—C8—C9	153.73 (14)	O4—N1—C13—O2	3.0 (2)
O1—C7—C8—Br1	91.78 (16)	O3—N1—C13—O2	−176.98 (15)
C6—C7—C8—Br1	−87.98 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O5i	0.93	2.48	3.211 (2)	136
C12—H12A···O3ii	0.93	2.43	3.317 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O5i	0.93	2.48	3.211 (2)	136
C12—H12A⋯O3ii	0.93	2.43	3.317 (2)	160

Symmetry codes: (i) ; (ii) .