3-(3-Nitro-benzyl-idene)pentane-2,4-dione.

In the title mol-ecule, C(12)H(11)NO(4), the two acetyl C-C=O planes are inclined to the benzene ring at angles of 18.03 (8) and 80.75 (7)°. In the crystal, adjacent mol-ecules are linked into centrosymmetric dimers by pairs of C-H⋯O inter-actions.

Related literature

For metal-complexes with β-diketones, see: Youngme et al. (2007 ▶); Ma et al. (2005 ▶); Soldatov et al. (2003 ▶); Hinckley (1969 ▶).

Experimental

Crystal data

C12H11NO4

M = 233.22

Monoclinic,

a = 16.0634 (9) Å

b = 5.2470 (3) Å

c = 14.9774 (9) Å

β = 114.117 (1)°

V = 1152.18 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: none

4779 measured reflections

1998 independent reflections

1400 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.171

S = 1.07

1998 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043456/is2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043456/is2374Isup2.hkl

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

C12H11NO4	F(000) = 488
Mr = 233.22	Dx = 1.344 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1131 reflections
a = 16.0634 (9) Å	θ = 2.7–24.3°
b = 5.2470 (3) Å	µ = 0.10 mm−1
c = 14.9774 (9) Å	T = 298 K
β = 114.117 (1)°	Block, colorless
V = 1152.18 (12) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	1400 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 25.0°, θmin = 2.7°
φ and ω scans	h = −19→17
4779 measured reflections	k = −6→6
1998 independent reflections	l = −11→17

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.085P)2 + 0.2322P] where P = (Fo2 + 2Fc2)/3
1998 reflections	(Δ/σ)max = 0.015
156 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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
C1	0.37414 (19)	−0.0732 (5)	0.46603 (19)	0.0328 (7)
C2	0.31796 (19)	0.1238 (5)	0.4642 (2)	0.0359 (7)
C3	0.30722 (19)	0.1886 (5)	0.54900 (19)	0.0348 (7)
C4	0.3576 (2)	0.0531 (6)	0.6342 (2)	0.0405 (8)
C5	0.4149 (2)	−0.1425 (6)	0.6345 (2)	0.0458 (8)
C6	0.4239 (2)	−0.2098 (6)	0.5501 (2)	0.0399 (8)
C7	0.2427 (2)	0.3821 (5)	0.5535 (2)	0.0389 (8)
C8	0.1758 (2)	0.5058 (5)	0.4812 (2)	0.0361 (7)
C9	0.1551 (2)	0.4824 (5)	0.3737 (2)	0.0374 (7)
C10	0.0895 (2)	0.2825 (6)	0.3165 (2)	0.0536 (9)
C11	0.1120 (2)	0.6808 (6)	0.5006 (2)	0.0434 (8)
C12	0.1252 (3)	0.7457 (7)	0.6020 (2)	0.0606 (10)
H2	0.2871	0.2142	0.4066	0.043*
H4	0.3524	0.0957	0.6919	0.049*
H5	0.4478	−0.2299	0.6923	0.055*
H6	0.4621	−0.3426	0.5496	0.048*
H7	0.2494	0.4254	0.6163	0.047*
H10A	0.0808	0.2920	0.2492	0.080*
H10B	0.0322	0.3087	0.3211	0.080*
H10C	0.1132	0.1177	0.3423	0.080*
H12A	0.0831	0.8774	0.6004	0.091*
H12B	0.1865	0.8045	0.6380	0.091*
H12C	0.1146	0.5971	0.6333	0.091*
O1	0.34549 (17)	−0.0057 (5)	0.30328 (15)	0.0605 (7)
O2	0.4208 (2)	−0.3406 (5)	0.37212 (17)	0.0735 (9)
O3	0.19108 (17)	0.6251 (4)	0.33704 (16)	0.0612 (7)
O4	0.04744 (19)	0.7640 (5)	0.43075 (17)	0.0764 (9)
N1	0.38064 (17)	−0.1449 (5)	0.37404 (18)	0.0446 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0375 (16)	0.0307 (15)	0.0255 (15)	−0.0020 (13)	0.0081 (12)	0.0000 (12)
C2	0.0389 (18)	0.0356 (17)	0.0271 (15)	0.0044 (14)	0.0073 (13)	0.0059 (13)
C3	0.0415 (18)	0.0329 (16)	0.0252 (15)	0.0022 (14)	0.0086 (13)	0.0008 (12)
C4	0.0454 (19)	0.0436 (18)	0.0279 (16)	0.0054 (16)	0.0101 (14)	0.0034 (13)
C5	0.053 (2)	0.0437 (19)	0.0331 (18)	0.0134 (16)	0.0098 (15)	0.0120 (14)
C6	0.0411 (18)	0.0362 (17)	0.0372 (17)	0.0087 (14)	0.0106 (14)	0.0055 (13)
C7	0.0489 (19)	0.0360 (17)	0.0276 (15)	0.0043 (15)	0.0113 (14)	0.0002 (13)
C8	0.0436 (18)	0.0282 (15)	0.0318 (16)	0.0010 (14)	0.0106 (13)	−0.0005 (12)
C9	0.0459 (19)	0.0255 (15)	0.0337 (17)	0.0109 (14)	0.0090 (14)	0.0030 (13)
C10	0.060 (2)	0.049 (2)	0.0380 (18)	−0.0040 (17)	0.0067 (16)	−0.0081 (15)
C11	0.051 (2)	0.0351 (17)	0.0397 (18)	0.0093 (16)	0.0144 (16)	0.0029 (15)
C12	0.067 (2)	0.069 (2)	0.049 (2)	0.024 (2)	0.0270 (19)	−0.0043 (18)
O1	0.0875 (19)	0.0624 (16)	0.0339 (13)	0.0208 (14)	0.0272 (13)	0.0112 (12)
O2	0.099 (2)	0.0719 (18)	0.0522 (15)	0.0440 (16)	0.0329 (14)	−0.0027 (13)
O3	0.0875 (19)	0.0539 (15)	0.0387 (13)	−0.0124 (14)	0.0223 (13)	0.0093 (11)
O4	0.085 (2)	0.080 (2)	0.0463 (15)	0.0496 (16)	0.0092 (14)	0.0050 (13)
N1	0.0504 (17)	0.0471 (16)	0.0372 (15)	0.0072 (14)	0.0187 (13)	−0.0009 (13)

C1—C6	1.384 (4)	C8—C9	1.511 (4)
C2—C1	1.365 (4)	C9—C10	1.485 (4)
C2—H2	0.9300	C10—H10A	0.9600
C3—C2	1.392 (4)	C10—H10B	0.9600
C3—C4	1.394 (4)	C10—H10C	0.9600
C3—C7	1.472 (4)	C11—C12	1.486 (4)
C4—C5	1.377 (4)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—C6	1.376 (4)	C12—H12C	0.9600
C5—H5	0.9300	O3—C9	1.206 (4)
C6—H6	0.9300	O4—C11	1.214 (3)
C7—H7	0.9300	N1—O1	1.219 (3)
C8—C7	1.341 (4)	N1—O2	1.219 (3)
C8—C11	1.490 (4)	N1—C1	1.472 (4)
C1—C6—H6	121.2	C9—C10—H10A	109.5
C1—C2—C3	119.6 (3)	C9—C10—H10B	109.5
C1—C2—H2	120.2	C9—C10—H10C	109.5
C2—C3—C4	117.9 (3)	C10—C9—C8	117.8 (3)
C2—C3—C7	124.2 (2)	C11—C8—C9	112.9 (2)
C2—C1—C6	122.8 (3)	C11—C12—H12A	109.5
C2—C1—N1	118.3 (2)	C11—C12—H12B	109.5
C3—C2—H2	120.2	C11—C12—H12C	109.5
C3—C7—H7	114.9	C12—C11—C8	121.2 (3)
C3—C4—H4	119.3	H10A—C10—H10B	109.5
C4—C3—C7	117.8 (3)	H10A—C10—H10C	109.5
C4—C5—H5	119.7	H10B—C10—H10C	109.5
C5—C6—C1	117.7 (3)	H12A—C12—H12B	109.5
C5—C6—H6	121.1	H12A—C12—H12C	109.5
C5—C4—C3	121.4 (3)	H12B—C12—H12C	109.5
C5—C4—H4	119.3	O1—N1—O2	123.1 (3)
C6—C1—N1	118.9 (3)	O1—N1—C1	118.4 (2)
C6—C5—C4	120.6 (3)	O2—N1—C1	118.5 (3)
C6—C5—H5	119.7	O3—C9—C10	122.4 (3)
C7—C8—C11	121.9 (3)	O3—C9—C8	119.8 (3)
C7—C8—C9	125.2 (3)	O4—C11—C12	120.9 (3)
C8—C7—C3	130.1 (3)	O4—C11—C8	117.8 (3)
C8—C7—H7	114.9
C2—C1—C6—C5	0.5 (5)	C7—C8—C11—O4	−172.3 (3)
C2—C3—C4—C5	−1.3 (5)	C7—C8—C11—C12	6.0 (5)
C2—C3—C7—C8	9.8 (5)	C9—C8—C11—O4	6.7 (4)
C3—C2—C1—C6	−1.9 (5)	C9—C8—C11—C12	−175.1 (3)
C3—C2—C1—N1	177.1 (2)	C9—C8—C7—C3	−4.2 (5)
C3—C4—C5—C6	−0.1 (5)	C11—C8—C7—C3	174.6 (3)
C4—C5—C6—C1	0.5 (5)	C11—C8—C9—O3	90.6 (4)
C4—C3—C2—C1	2.3 (4)	C11—C8—C9—C10	−88.8 (3)
C4—C3—C7—C8	−167.0 (3)	O1—N1—C1—C2	9.6 (4)
C7—C3—C4—C5	175.7 (3)	O1—N1—C1—C6	−171.4 (3)
C7—C8—C9—O3	−90.5 (4)	O2—N1—C1—C6	8.7 (4)
C7—C3—C2—C1	−174.5 (3)	O2—N1—C1—C2	−170.3 (3)
C7—C8—C9—C10	90.1 (4)	N1—C1—C6—C5	−178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.42	3.282 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.42	3.282 (4)	153

Symmetry code: (i) .