3-(5-Nitro-2-fur-yl)-1-phenyl-prop-2-yn-1-one.

In the title compound, C(13)H(7)NO(4), the 2-furyl ring is essentially planar, with a maximum deviation of 0.004 (1) Å. It is inclined at an angle of 11.69 (4)° to the benzene ring. The nitro group is slightly twisted out of the plane of the 2-furyl ring, with a dihedral angle of 5.72 (8)°. There is a short O⋯C contact of 2.8562 (8) Å (symmetry code: -x, -y, 2 - z). In the crystal packing, mol-ecules are linked via a pair of inter-molecular C-H⋯O hydrogen bonds, giving rise to an R(2) (2)(10) ring motif. Mol-ecules are further linked into two-dimensional networks parallel to [100] via other inter-molecular C-H⋯O hydrogen bonds. The crystal structure is consolidated by C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C13H7NO4

M = 241.20

Monoclinic,

a = 10.4685 (2) Å

b = 7.3006 (1) Å

c = 15.2642 (2) Å

β = 110.867 (1)°

V = 1090.07 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.47 × 0.38 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.970

40673 measured reflections

5796 independent reflections

4934 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.04

5796 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.33 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/S1600536810043850/fj2357sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043850/fj2357Isup2.hkl

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

C13H7NO4	F(000) = 496
Mr = 241.20	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9876 reflections
a = 10.4685 (2) Å	θ = 2.8–37.6°
b = 7.3006 (1) Å	µ = 0.11 mm−1
c = 15.2642 (2) Å	T = 100 K
β = 110.867 (1)°	Block, brown
V = 1090.07 (3) Å3	0.47 × 0.38 × 0.28 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5796 independent reflections
Radiation source: fine-focus sealed tube	4934 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 37.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.950, Tmax = 0.970	k = −12→12
40673 measured reflections	l = −25→26

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1893P] where P = (Fo2 + 2Fc2)/3
5796 reflections	(Δ/σ)max = 0.002
163 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.33 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
O1	−0.11630 (5)	0.27415 (7)	1.04906 (3)	0.01471 (9)
O2	−0.39290 (6)	0.35131 (8)	1.11730 (4)	0.02350 (11)
O3	−0.19217 (6)	0.23310 (8)	1.19322 (4)	0.02173 (10)
O4	0.31281 (5)	0.03921 (7)	0.98678 (3)	0.01702 (9)
N1	−0.27662 (6)	0.30540 (8)	1.12394 (4)	0.01630 (10)
C1	−0.23941 (6)	0.33853 (8)	1.04384 (4)	0.01429 (10)
C2	−0.31207 (6)	0.41459 (9)	0.95952 (5)	0.01643 (11)
H2	−0.3984	0.4675	0.9412	0.020*
C3	−0.22679 (6)	0.39527 (9)	0.90560 (5)	0.01704 (11)
H3	−0.2463	0.4335	0.8441	0.020*
C4	−0.11011 (6)	0.30936 (9)	0.96198 (4)	0.01464 (10)
C5	0.00843 (6)	0.25151 (9)	0.94661 (5)	0.01623 (11)
C6	0.10953 (6)	0.20010 (9)	0.93282 (4)	0.01633 (11)
C7	0.23677 (6)	0.13782 (8)	0.92494 (4)	0.01320 (10)
C8	0.27014 (6)	0.19941 (8)	0.84344 (4)	0.01292 (10)
C9	0.17614 (7)	0.29769 (9)	0.76987 (4)	0.01676 (11)
H9	0.0897	0.3240	0.7707	0.020*
C10	0.21317 (8)	0.35576 (10)	0.69539 (5)	0.02011 (12)
H10	0.1514	0.4214	0.6463	0.024*
C11	0.34271 (8)	0.31575 (10)	0.69438 (5)	0.02020 (12)
H11	0.3673	0.3559	0.6448	0.024*
C12	0.43585 (7)	0.21588 (10)	0.76724 (5)	0.01871 (11)
H12	0.5219	0.1886	0.7658	0.022*
C13	0.39983 (6)	0.15728 (9)	0.84181 (4)	0.01523 (10)
H13	0.4615	0.0904	0.8904	0.018*

	U11	U22	U33	U12	U13	U23
O1	0.01147 (17)	0.01760 (19)	0.01634 (19)	0.00183 (14)	0.00653 (14)	0.00090 (15)
O2	0.0173 (2)	0.0286 (3)	0.0299 (3)	0.00376 (18)	0.0150 (2)	−0.0001 (2)
O3	0.0219 (2)	0.0261 (2)	0.0180 (2)	0.00245 (18)	0.00804 (18)	0.00227 (18)
O4	0.0181 (2)	0.0185 (2)	0.01441 (18)	0.00230 (15)	0.00568 (15)	0.00193 (15)
N1	0.0158 (2)	0.0164 (2)	0.0192 (2)	0.00019 (17)	0.00932 (18)	−0.00110 (17)
C1	0.0117 (2)	0.0154 (2)	0.0176 (2)	0.00109 (17)	0.00733 (18)	−0.00024 (18)
C2	0.0131 (2)	0.0173 (2)	0.0191 (2)	0.00249 (18)	0.00597 (19)	0.00072 (19)
C3	0.0155 (2)	0.0189 (3)	0.0172 (2)	0.00230 (19)	0.00642 (19)	0.00149 (19)
C4	0.0132 (2)	0.0159 (2)	0.0166 (2)	0.00058 (17)	0.00742 (18)	−0.00012 (18)
C5	0.0143 (2)	0.0174 (2)	0.0190 (2)	−0.00023 (18)	0.0085 (2)	−0.00129 (19)
C6	0.0148 (2)	0.0186 (3)	0.0177 (2)	0.00069 (19)	0.00826 (19)	−0.00003 (19)
C7	0.0124 (2)	0.0142 (2)	0.0139 (2)	−0.00032 (16)	0.00575 (17)	−0.00142 (17)
C8	0.0122 (2)	0.0142 (2)	0.0128 (2)	0.00024 (16)	0.00488 (17)	0.00001 (16)
C9	0.0150 (2)	0.0180 (2)	0.0157 (2)	0.00193 (19)	0.00354 (19)	0.00166 (19)
C10	0.0241 (3)	0.0193 (3)	0.0146 (2)	−0.0002 (2)	0.0040 (2)	0.0030 (2)
C11	0.0263 (3)	0.0213 (3)	0.0146 (2)	−0.0062 (2)	0.0092 (2)	−0.0006 (2)
C12	0.0179 (3)	0.0233 (3)	0.0179 (2)	−0.0032 (2)	0.0100 (2)	−0.0016 (2)
C13	0.0126 (2)	0.0190 (2)	0.0150 (2)	0.00056 (18)	0.00601 (18)	0.00020 (18)

O1—C1	1.3472 (7)	C6—C7	1.4525 (8)
O1—C4	1.3779 (8)	C7—C8	1.4770 (8)
O2—N1	1.2315 (7)	C8—C9	1.3990 (8)
O3—N1	1.2298 (8)	C8—C13	1.4010 (8)
O4—C7	1.2278 (8)	C9—C10	1.3915 (9)
N1—C1	1.4298 (8)	C9—H9	0.9300
C1—C2	1.3586 (9)	C10—C11	1.3927 (11)
C2—C3	1.4205 (9)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.3953 (10)
C3—C4	1.3701 (9)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.3880 (9)
C4—C5	1.4073 (8)	C12—H12	0.9300
C5—C6	1.2100 (8)	C13—H13	0.9300
C1—O1—C4	104.51 (5)	C6—C7—C8	118.26 (5)
O3—N1—O2	125.05 (6)	C9—C8—C13	120.49 (5)
O3—N1—C1	118.47 (5)	C9—C8—C7	121.50 (5)
O2—N1—C1	116.48 (6)	C13—C8—C7	118.01 (5)
O1—C1—C2	113.56 (5)	C10—C9—C8	119.41 (6)
O1—C1—N1	115.88 (5)	C10—C9—H9	120.3
C2—C1—N1	130.40 (5)	C8—C9—H9	120.3
C1—C2—C3	104.66 (5)	C9—C10—C11	120.06 (6)
C1—C2—H2	127.7	C9—C10—H10	120.0
C3—C2—H2	127.7	C11—C10—H10	120.0
C4—C3—C2	106.57 (6)	C10—C11—C12	120.49 (6)
C4—C3—H3	126.7	C10—C11—H11	119.8
C2—C3—H3	126.7	C12—C11—H11	119.8
C3—C4—O1	110.71 (5)	C13—C12—C11	119.86 (6)
C3—C4—C5	132.41 (6)	C13—C12—H12	120.1
O1—C4—C5	116.88 (5)	C11—C12—H12	120.1
C6—C5—C4	179.25 (7)	C12—C13—C8	119.67 (6)
C5—C6—C7	175.08 (7)	C12—C13—H13	120.2
O4—C7—C6	118.85 (5)	C8—C13—H13	120.2
O4—C7—C8	122.88 (5)
C4—O1—C1—C2	−0.69 (7)	O4—C7—C8—C9	174.06 (6)
C4—O1—C1—N1	175.17 (5)	C6—C7—C8—C9	−7.19 (9)
O3—N1—C1—O1	4.75 (9)	O4—C7—C8—C13	−6.23 (9)
O2—N1—C1—O1	−174.73 (6)	C6—C7—C8—C13	172.52 (6)
O3—N1—C1—C2	179.76 (7)	C13—C8—C9—C10	−0.90 (10)
O2—N1—C1—C2	0.28 (11)	C7—C8—C9—C10	178.80 (6)
O1—C1—C2—C3	0.46 (8)	C8—C9—C10—C11	0.11 (10)
N1—C1—C2—C3	−174.65 (7)	C9—C10—C11—C12	0.64 (11)
C1—C2—C3—C4	−0.02 (7)	C10—C11—C12—C13	−0.61 (11)
C2—C3—C4—O1	−0.40 (7)	C11—C12—C13—C8	−0.18 (10)
C2—C3—C4—C5	178.65 (7)	C9—C8—C13—C12	0.93 (10)
C1—O1—C4—C3	0.65 (7)	C7—C8—C13—C12	−178.78 (6)
C1—O1—C4—C5	−178.56 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.44	3.3548 (9)	170
C11—H11···O4ii	0.93	2.40	3.2487 (9)	152
C3—H3···Cg1iii	0.93	2.86	3.6284 (7)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the phenyl (C8–C12) ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.44	3.3548 (9)	170
C11—H11⋯O4ii	0.93	2.40	3.2487 (9)	152
C3—H3⋯Cg1iii	0.93	2.86	3.6284 (7)	141

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