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

In the title compound, C(13)H(9)Br(2)NO(4), the phenyl and 2-nitro-furan rings are linked by a 2,3-dibromo-propanal group, six atoms of which, including a furyl C atom, are disordered over two positions with a site-occupancy ratio of 0.733 (11):0.267 (11). The dihedral angle between the furan [maximum deviation = 0.028 (4) Å] and phenyl rings in the major component is 16.9 (3)°. In the minor component, the corresponding values are 0.87 (4) Å and 23.3 (5)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into two-dimensional arrays parallel to the ab plane.

Related literature

For the biological activity of sydnones, see: Holla et al. (1986 ▶, 1987 ▶, 1992 ▶); Rai et al. (2008 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶). 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 ▶).

Experimental

Crystal data

C13H9Br2NO4

M = 403.03

Triclinic,

a = 8.6939 (7) Å

b = 8.7834 (8) Å

c = 10.4722 (9) Å

α = 89.334 (2)°

β = 69.846 (2)°

γ = 68.114 (2)°

V = 690.32 (10) Å3

Z = 2

Mo Kα radiation

μ = 5.88 mm−1

T = 100 K

0.28 × 0.18 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.292, T max = 0.644

10644 measured reflections

4015 independent reflections

3390 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.33

4015 reflections

216 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.60 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/S1600536811003552/sj5095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003552/sj5095Isup2.hkl

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

C13H9Br2NO4	Z = 2
Mr = 403.03	F(000) = 392
Triclinic, P1	Dx = 1.939 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6939 (7) Å	Cell parameters from 4381 reflections
b = 8.7834 (8) Å	θ = 2.7–29.9°
c = 10.4722 (9) Å	µ = 5.88 mm−1
α = 89.334 (2)°	T = 100 K
β = 69.846 (2)°	Block, colourless
γ = 68.114 (2)°	0.28 × 0.18 × 0.08 mm
V = 690.32 (10) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4015 independent reflections
Radiation source: fine-focus sealed tube	3390 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.292, Tmax = 0.644	k = −12→12
10644 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.33	w = 1/[σ2(Fo2) + (0.P)2 + 1.8339P] where P = (Fo2 + 2Fc2)/3
4015 reflections	(Δ/σ)max = 0.004
216 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.60 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 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	0.5867 (5)	−0.0270 (6)	0.3027 (5)	0.0390 (6)	0.733 (11)
Br2A	0.3391 (5)	0.3650 (6)	0.0580 (4)	0.0351 (7)	0.733 (11)
Br1B	0.3448 (12)	0.3749 (13)	0.0447 (8)	0.0197 (10)	0.267 (11)
Br2B	0.5581 (11)	−0.0069 (17)	0.3178 (13)	0.0296 (14)	0.267 (11)
O1	0.2667 (4)	0.0406 (4)	0.1625 (3)	0.0338 (7)
O2A	0.6226 (6)	0.3610 (7)	0.2085 (5)	0.0189 (9)	0.733 (11)
O2B	0.6469 (19)	0.3223 (18)	0.2302 (15)	0.018 (3)*	0.267 (11)
O3	0.6434 (4)	0.5677 (4)	0.3755 (3)	0.0325 (6)
O4	0.8888 (4)	0.5635 (4)	0.2207 (3)	0.0415 (8)
N1	0.7672 (4)	0.5148 (4)	0.2642 (3)	0.0249 (6)
C1	−0.0571 (5)	0.1488 (5)	0.3829 (4)	0.0212 (7)
H1A	−0.0479	0.0924	0.3043	0.025*
C2	−0.2122 (5)	0.1970 (5)	0.4979 (4)	0.0253 (7)
H2A	−0.3084	0.1755	0.4960	0.030*
C3	−0.2236 (5)	0.2777 (5)	0.6167 (4)	0.0294 (8)
H3A	−0.3274	0.3095	0.6943	0.035*
C4	−0.0827 (5)	0.3104 (6)	0.6197 (4)	0.0323 (9)
H4A	−0.0907	0.3625	0.7000	0.039*
C5	0.0721 (5)	0.2667 (5)	0.5041 (4)	0.0292 (8)
H5A	0.1662	0.2918	0.5062	0.035*
C6	0.0856 (5)	0.1849 (5)	0.3846 (4)	0.0228 (7)
C7	0.2483 (5)	0.1296 (5)	0.2579 (4)	0.0247 (7)
C8A	0.4061 (7)	0.1730 (7)	0.2557 (5)	0.0216 (12)	0.733 (11)
H8AA	0.3645	0.2723	0.3204	0.026*	0.733 (11)
C9A	0.5127 (6)	0.1929 (6)	0.1129 (5)	0.0193 (12)	0.733 (11)
H9AA	0.5601	0.0895	0.0515	0.023*	0.733 (11)
C10A	0.6591 (8)	0.2419 (8)	0.1058 (6)	0.0203 (11)	0.733 (11)
C8B	0.3734 (19)	0.229 (2)	0.2179 (16)	0.021 (3)*	0.267 (11)
H8BA	0.3511	0.3022	0.2981	0.025*	0.267 (11)
C9B	0.5672 (17)	0.1115 (16)	0.1590 (13)	0.018 (3)*	0.267 (11)
H9BA	0.5921	0.0391	0.0776	0.022*	0.267 (11)
C10B	0.688 (2)	0.200 (2)	0.1295 (18)	0.019 (4)*	0.267 (11)
C11	0.8299 (5)	0.1960 (5)	0.0144 (4)	0.0253 (8)
H11A	0.8883	0.1133	−0.0605	0.030*
C12	0.9001 (5)	0.2992 (5)	0.0562 (4)	0.0240 (7)
H12A	1.0104	0.3042	0.0109	0.029*
C13	0.7741 (5)	0.3889 (5)	0.1753 (4)	0.0214 (7)

	U11	U22	U33	U12	U13	U23
Br1A	0.0594 (17)	0.0360 (9)	0.0387 (12)	−0.0285 (13)	−0.0276 (13)	0.0186 (8)
Br2A	0.0317 (11)	0.0294 (7)	0.0539 (16)	−0.0122 (6)	−0.0269 (10)	0.0123 (8)
Br1B	0.0144 (15)	0.026 (2)	0.0159 (13)	−0.0064 (14)	−0.0040 (10)	0.0003 (13)
Br2B	0.0210 (13)	0.049 (4)	0.0275 (18)	−0.0201 (15)	−0.0118 (11)	0.017 (2)
O1	0.0328 (15)	0.0468 (19)	0.0237 (14)	−0.0266 (14)	0.0000 (12)	−0.0101 (12)
O2A	0.0164 (18)	0.022 (2)	0.018 (2)	−0.0095 (17)	−0.0035 (16)	−0.0004 (17)
O3	0.0296 (14)	0.0340 (16)	0.0319 (15)	−0.0137 (13)	−0.0073 (12)	−0.0056 (12)
O4	0.0337 (16)	0.053 (2)	0.0443 (18)	−0.0308 (16)	−0.0064 (14)	−0.0062 (15)
N1	0.0224 (14)	0.0256 (16)	0.0300 (17)	−0.0107 (13)	−0.0117 (13)	0.0014 (13)
C1	0.0196 (15)	0.0248 (18)	0.0199 (16)	−0.0109 (14)	−0.0055 (13)	0.0004 (13)
C2	0.0197 (16)	0.029 (2)	0.0276 (19)	−0.0124 (15)	−0.0056 (14)	0.0034 (15)
C3	0.0229 (18)	0.034 (2)	0.029 (2)	−0.0116 (16)	−0.0062 (15)	−0.0009 (16)
C4	0.0281 (19)	0.042 (2)	0.0228 (19)	−0.0168 (18)	−0.0010 (15)	−0.0096 (16)
C5	0.0233 (17)	0.039 (2)	0.0235 (18)	−0.0166 (17)	−0.0010 (14)	−0.0095 (16)
C6	0.0211 (16)	0.0255 (18)	0.0207 (17)	−0.0118 (14)	−0.0033 (13)	−0.0018 (13)
C7	0.0212 (16)	0.0291 (19)	0.0222 (17)	−0.0146 (15)	−0.0008 (14)	−0.0042 (14)
C8A	0.020 (2)	0.024 (3)	0.022 (2)	−0.012 (2)	−0.0047 (19)	0.001 (2)
C9A	0.018 (2)	0.021 (3)	0.018 (2)	−0.0080 (18)	−0.0042 (17)	−0.0023 (17)
C10A	0.022 (3)	0.019 (3)	0.021 (3)	−0.008 (2)	−0.008 (2)	0.002 (2)
C11	0.0210 (17)	0.029 (2)	0.0205 (17)	−0.0097 (15)	−0.0014 (14)	−0.0038 (14)
C12	0.0154 (15)	0.029 (2)	0.0251 (18)	−0.0089 (14)	−0.0039 (13)	0.0019 (14)
C13	0.0183 (15)	0.0254 (18)	0.0239 (17)	−0.0126 (14)	−0.0074 (13)	0.0026 (13)

Br1A—C8A	2.061 (7)	C4—H4A	0.9300
Br2A—C9A	1.942 (7)	C5—C6	1.398 (5)
Br1B—C8B	2.24 (2)	C5—H5A	0.9300
Br2B—C9B	1.944 (18)	C6—C7	1.485 (5)
O1—C7	1.205 (5)	C7—C8A	1.547 (6)
O2A—C13	1.356 (5)	C7—C8B	1.586 (15)
O2A—C10A	1.376 (7)	C8A—C9A	1.512 (7)
O2B—C10B	1.37 (2)	C8A—H8AA	0.9800
O2B—C13	1.390 (15)	C9A—C10A	1.468 (7)
O3—N1	1.228 (4)	C9A—H9AA	0.9800
O4—N1	1.229 (4)	C10A—C11	1.366 (6)
N1—C13	1.424 (5)	C8B—C9B	1.513 (19)
C1—C2	1.384 (5)	C8B—H8BA	0.9800
C1—C6	1.396 (5)	C9B—C10B	1.48 (2)
C1—H1A	0.9300	C9B—H9BA	0.9800
C2—C3	1.394 (6)	C10B—C11	1.382 (17)
C2—H2A	0.9300	C11—C12	1.411 (5)
C3—C4	1.369 (6)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.347 (5)
C4—C5	1.388 (5)	C12—H12A	0.9300
C13—O2A—C10A	104.7 (4)	C8A—C9A—Br2A	104.1 (3)
C10B—O2B—C13	103.9 (12)	C10A—C9A—H9AA	109.5
O3—N1—O4	124.8 (3)	C8A—C9A—H9AA	109.5
O3—N1—C13	119.5 (3)	Br2A—C9A—H9AA	109.5
O4—N1—C13	115.7 (3)	C11—C10A—O2A	110.5 (4)
C2—C1—C6	120.1 (3)	C11—C10A—C9A	133.2 (5)
C2—C1—H1A	119.9	O2A—C10A—C9A	116.3 (4)
C6—C1—H1A	119.9	C9B—C8B—C7	110.4 (11)
C1—C2—C3	119.8 (3)	C9B—C8B—Br1B	102.2 (9)
C1—C2—H2A	120.1	C7—C8B—Br1B	112.9 (9)
C3—C2—H2A	120.1	C9B—C8B—H8BA	110.4
C4—C3—C2	120.3 (4)	C7—C8B—H8BA	110.4
C4—C3—H3A	119.8	Br1B—C8B—H8BA	110.4
C2—C3—H3A	119.8	C10B—C9B—C8B	111.8 (12)
C3—C4—C5	120.7 (4)	C10B—C9B—Br2B	114.8 (11)
C3—C4—H4A	119.7	C8B—C9B—Br2B	95.2 (9)
C5—C4—H4A	119.7	C10B—C9B—H9BA	111.3
C4—C5—C6	119.6 (4)	C8B—C9B—H9BA	111.3
C4—C5—H5A	120.2	Br2B—C9B—H9BA	111.3
C6—C5—H5A	120.2	O2B—C10B—C11	111.1 (14)
C1—C6—C5	119.6 (3)	O2B—C10B—C9B	115.5 (14)
C1—C6—C7	117.5 (3)	C11—C10B—C9B	133.2 (15)
C5—C6—C7	123.0 (3)	C10A—C11—C10B	20.1 (6)
O1—C7—C6	122.0 (3)	C10A—C11—C12	106.3 (4)
O1—C7—C8A	119.2 (3)	C10B—C11—C12	105.3 (8)
C6—C7—C8A	118.5 (3)	C10A—C11—H11A	126.8
O1—C7—C8B	113.5 (6)	C10B—C11—H11A	124.3
C6—C7—C8B	121.2 (6)	C12—C11—H11A	126.8
C8A—C7—C8B	24.7 (5)	C13—C12—C11	105.7 (3)
C9A—C8A—C7	111.9 (4)	C13—C12—H12A	127.1
C9A—C8A—Br1A	103.2 (3)	C11—C12—H12A	127.1
C7—C8A—Br1A	108.7 (4)	C12—C13—O2A	112.5 (4)
C9A—C8A—H8AA	110.9	C12—C13—O2B	111.5 (7)
C7—C8A—H8AA	110.9	O2A—C13—O2B	18.2 (5)
Br1A—C8A—H8AA	110.9	C12—C13—N1	131.7 (3)
C10A—C9A—C8A	114.2 (4)	O2A—C13—N1	115.6 (3)
C10A—C9A—Br2A	109.9 (4)	O2B—C13—N1	115.6 (7)
C6—C1—C2—C3	−1.7 (6)	C7—C8B—C9B—C10B	−176.0 (12)
C1—C2—C3—C4	0.4 (6)	Br1B—C8B—C9B—C10B	63.7 (13)
C2—C3—C4—C5	1.2 (7)	C7—C8B—C9B—Br2B	−56.6 (11)
C3—C4—C5—C6	−1.6 (7)	Br1B—C8B—C9B—Br2B	−176.9 (7)
C2—C1—C6—C5	1.3 (6)	C13—O2B—C10B—C11	−2.7 (15)
C2—C1—C6—C7	179.9 (4)	C13—O2B—C10B—C9B	−177.7 (12)
C4—C5—C6—C1	0.3 (6)	C8B—C9B—C10B—O2B	45.3 (18)
C4—C5—C6—C7	−178.2 (4)	Br2B—C9B—C10B—O2B	−61.8 (16)
C1—C6—C7—O1	−8.5 (6)	C8B—C9B—C10B—C11	−128.2 (19)
C5—C6—C7—O1	170.0 (4)	Br2B—C9B—C10B—C11	124.7 (17)
C1—C6—C7—C8A	178.1 (4)	O2A—C10A—C11—C10B	86 (3)
C5—C6—C7—C8A	−3.4 (6)	C9A—C10A—C11—C10B	−96 (3)
C1—C6—C7—C8B	149.7 (8)	O2A—C10A—C11—C12	−4.1 (7)
C5—C6—C7—C8B	−31.8 (9)	C9A—C10A—C11—C12	174.2 (7)
O1—C7—C8A—C9A	36.3 (6)	O2B—C10B—C11—C10A	−84 (3)
C6—C7—C8A—C9A	−150.1 (4)	C9B—C10B—C11—C10A	89 (3)
C8B—C7—C8A—C9A	−46.6 (14)	O2B—C10B—C11—C12	11.5 (14)
O1—C7—C8A—Br1A	−77.1 (5)	C9B—C10B—C11—C12	−174.8 (16)
C6—C7—C8A—Br1A	96.5 (4)	C10A—C11—C12—C13	5.3 (5)
C8B—C7—C8A—Br1A	−159.9 (15)	C10B—C11—C12—C13	−15.6 (9)
C7—C8A—C9A—C10A	177.2 (5)	C11—C12—C13—O2A	−4.7 (5)
Br1A—C8A—C9A—C10A	−66.1 (5)	C11—C12—C13—O2B	14.9 (7)
C7—C8A—C9A—Br2A	57.4 (5)	C11—C12—C13—N1	−178.8 (4)
Br1A—C8A—C9A—Br2A	174.0 (3)	C10A—O2A—C13—C12	2.2 (6)
C13—O2A—C10A—C11	1.3 (7)	C10A—O2A—C13—O2B	−88 (3)
C13—O2A—C10A—C9A	−177.3 (5)	C10A—O2A—C13—N1	177.3 (4)
C8A—C9A—C10A—C11	139.8 (8)	C10B—O2B—C13—C12	−7.8 (12)
Br2A—C9A—C10A—C11	−103.6 (8)	C10B—O2B—C13—O2A	89 (3)
C8A—C9A—C10A—O2A	−41.9 (7)	C10B—O2B—C13—N1	−176.6 (9)
Br2A—C9A—C10A—O2A	74.7 (6)	O3—N1—C13—C12	−172.8 (4)
O1—C7—C8B—C9B	−59.4 (13)	O4—N1—C13—C12	7.9 (6)
C6—C7—C8B—C9B	140.8 (9)	O3—N1—C13—O2A	13.3 (6)
C8A—C7—C8B—C9B	49.9 (13)	O4—N1—C13—O2A	−166.0 (4)
O1—C7—C8B—Br1B	54.3 (9)	O3—N1—C13—O2B	−6.9 (8)
C6—C7—C8B—Br1B	−105.5 (7)	O4—N1—C13—O2B	173.8 (7)
C8A—C7—C8B—Br1B	163.6 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C9A—H9AA···O1i	0.98	2.25	3.098 (6)	145
C4—H4A···O4ii	0.93	2.46	3.200 (6)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9A—H9AA⋯O1i	0.98	2.25	3.098 (6)	145
C4—H4A⋯O4ii	0.93	2.46	3.200 (6)	136

Symmetry codes: (i) ; (ii) .