4,4-Dimethyl-1-(3-nitro-phen-yl)pent-1-en-3-one.

All the non-hydrogen atoms except one methyl C atom of the title compound, C(13)H(15)NO(3), lie on a crystallographic mirror plane perpendicular to the b axis. The crystal packing is stabilized by two weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

The title compound is an important intermediate in the pesticides industry (Wang et al., 2006 ▶). For related structures, see: Anuradha et al. (2008 ▶); Butcher et al. (2007 ▶); Gong et al. (2008 ▶); Harrison et al. (2007 ▶); Patil et al. (2007 ▶); Sarojini et al. (2007 ▶); Thiruvalluvar et al. (2007 ▶, 2008 ▶); Xia & Hu (2008 ▶).

Experimental

Crystal data

C13H15NO3

M = 233.26

Orthorhombic,

a = 11.3375 (9) Å

b = 7.2163 (6) Å

c = 14.9327 (12) Å

V = 1221.72 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.48 × 0.36 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.958, T max = 0.987

5485 measured reflections

1280 independent reflections

937 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.06

1280 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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/S1600536809018479/bt2958sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018479/bt2958Isup2.hkl

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

C13H15NO3	Dx = 1.268 Mg m−3
Mr = 233.26	Melting point: 363 K
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1920 reflections
a = 11.3375 (9) Å	θ = 2.3–27.7°
b = 7.2163 (6) Å	µ = 0.09 mm−1
c = 14.9327 (12) Å	T = 173 K
V = 1221.72 (17) Å3	Block, colourless
Z = 4	0.48 × 0.36 × 0.15 mm
F(000) = 496

Bruker SMART 1000 CCD diffractometer	1280 independent reflections
Radiation source: fine-focus sealed tube	937 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→12
Tmin = 0.958, Tmax = 0.987	k = −3→8
5485 measured reflections	l = −18→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.3634P] where P = (Fo2 + 2Fc2)/3
1280 reflections	(Δ/σ)max = 0.001
101 parameters	Δρmax = 0.26 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	Occ. (<1)
C1	0.64133 (19)	0.2500	0.12364 (15)	0.0363 (6)
H1	0.7249	0.2500	0.1281	0.044*
C2	0.5825 (2)	0.2500	0.19956 (15)	0.0371 (6)
H2	0.4987	0.2500	0.1983	0.045*
C3	0.6446 (2)	0.2500	0.28774 (15)	0.0367 (6)
C4	0.56797 (18)	0.2500	0.37208 (15)	0.0317 (5)
C5	0.6474 (2)	0.2500	0.45437 (16)	0.0392 (6)
H5A	0.5987	0.2500	0.5086	0.059*
H5B	0.6973	0.3609	0.4537	0.059*	0.50
H5C	0.6973	0.1391	0.4537	0.059*	0.50
C6	0.48919 (15)	0.0777 (3)	0.37212 (12)	0.0419 (5)
H6A	0.5385	−0.0338	0.3701	0.063*
H6B	0.4374	0.0803	0.3196	0.063*
H6C	0.4412	0.0761	0.4267	0.063*
C7	0.59173 (19)	0.2500	0.03248 (15)	0.0310 (5)
C8	0.66910 (19)	0.2500	−0.03967 (15)	0.0313 (5)
H8	0.7519	0.2500	−0.0299	0.038*
C9	0.62418 (18)	0.2500	−0.12592 (14)	0.0296 (5)
C10	0.5051 (2)	0.2500	−0.14355 (15)	0.0348 (6)
H10	0.4764	0.2500	−0.2033	0.042*
C11	0.42813 (19)	0.2500	−0.07129 (16)	0.0381 (6)
H11	0.3454	0.2500	−0.0814	0.046*
C12	0.47098 (19)	0.2500	0.01538 (15)	0.0363 (6)
H12	0.4171	0.2500	0.0641	0.044*
N1	0.70773 (17)	0.2500	−0.20150 (12)	0.0359 (5)
O1	0.66864 (16)	0.2500	−0.27777 (11)	0.0501 (5)
O2	0.81309 (15)	0.2500	−0.18457 (12)	0.0570 (6)
O3	0.75145 (14)	0.2500	0.29171 (11)	0.0559 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0277 (11)	0.0469 (15)	0.0344 (13)	0.000	−0.0032 (9)	0.000
C2	0.0283 (11)	0.0495 (15)	0.0337 (13)	0.000	−0.0012 (9)	0.000
C3	0.0319 (12)	0.0453 (15)	0.0328 (13)	0.000	−0.0006 (9)	0.000
C4	0.0315 (11)	0.0347 (13)	0.0290 (12)	0.000	−0.0002 (9)	0.000
C5	0.0373 (12)	0.0471 (15)	0.0333 (13)	0.000	−0.0019 (10)	0.000
C6	0.0415 (9)	0.0424 (10)	0.0418 (10)	−0.0048 (8)	0.0023 (7)	0.0001 (8)
C7	0.0304 (11)	0.0317 (13)	0.0310 (12)	0.000	−0.0015 (9)	0.000
C8	0.0265 (10)	0.0332 (13)	0.0340 (13)	0.000	−0.0030 (9)	0.000
C9	0.0312 (11)	0.0281 (12)	0.0297 (12)	0.000	0.0014 (9)	0.000
C10	0.0352 (12)	0.0387 (14)	0.0306 (12)	0.000	−0.0043 (9)	0.000
C11	0.0279 (11)	0.0494 (15)	0.0372 (13)	0.000	−0.0014 (9)	0.000
C12	0.0321 (12)	0.0447 (14)	0.0322 (13)	0.000	0.0006 (9)	0.000
N1	0.0355 (11)	0.0405 (12)	0.0316 (12)	0.000	0.0020 (8)	0.000
O1	0.0501 (10)	0.0725 (14)	0.0278 (10)	0.000	−0.0010 (8)	0.000
O2	0.0322 (9)	0.0955 (16)	0.0434 (11)	0.000	0.0058 (8)	0.000
O3	0.0300 (10)	0.1027 (17)	0.0350 (10)	0.000	−0.0011 (7)	0.000

C1—C2	1.315 (3)	C6—H6C	0.9800
C1—C7	1.473 (3)	C7—C8	1.389 (3)
C1—H1	0.9500	C7—C12	1.393 (3)
C2—C3	1.493 (3)	C8—C9	1.385 (3)
C2—H2	0.9500	C8—H8	0.9500
C3—O3	1.213 (3)	C9—C10	1.376 (3)
C3—C4	1.530 (3)	C9—N1	1.474 (3)
C4—C5	1.523 (3)	C10—C11	1.388 (3)
C4—C6	1.531 (2)	C10—H10	0.9500
C4—C6i	1.531 (2)	C11—C12	1.382 (3)
C5—H5A	0.9800	C11—H11	0.9500
C5—H5B	0.9800	C12—H12	0.9500
C5—H5C	0.9800	N1—O2	1.221 (2)
C6—H6A	0.9800	N1—O1	1.222 (2)
C6—H6B	0.9800
C2—C1—C7	127.1 (2)	C4—C6—H6C	109.5
C2—C1—H1	116.5	H6A—C6—H6C	109.5
C7—C1—H1	116.5	H6B—C6—H6C	109.5
C1—C2—C3	121.4 (2)	C8—C7—C12	118.6 (2)
C1—C2—H2	119.3	C8—C7—C1	118.40 (19)
C3—C2—H2	119.3	C12—C7—C1	123.0 (2)
O3—C3—C2	120.9 (2)	C9—C8—C7	119.27 (19)
O3—C3—C4	121.8 (2)	C9—C8—H8	120.4
C2—C3—C4	117.30 (19)	C7—C8—H8	120.4
C5—C4—C3	109.19 (18)	C10—C9—C8	122.6 (2)
C5—C4—C6	110.15 (12)	C10—C9—N1	118.97 (19)
C3—C4—C6	109.36 (12)	C8—C9—N1	118.42 (18)
C5—C4—C6i	110.15 (12)	C9—C10—C11	117.9 (2)
C3—C4—C6i	109.36 (12)	C9—C10—H10	121.0
C6—C4—C6i	108.63 (18)	C11—C10—H10	121.0
C4—C5—H5A	109.5	C12—C11—C10	120.5 (2)
C4—C5—H5B	109.5	C12—C11—H11	119.8
H5A—C5—H5B	109.5	C10—C11—H11	119.8
C4—C5—H5C	109.5	C11—C12—C7	121.1 (2)
H5A—C5—H5C	109.5	C11—C12—H12	119.4
H5B—C5—H5C	109.5	C7—C12—H12	119.4
C4—C6—H6A	109.5	O2—N1—O1	123.22 (19)
C4—C6—H6B	109.5	O2—N1—C9	118.06 (18)
H6A—C6—H6B	109.5	O1—N1—C9	118.73 (18)
C7—C1—C2—C3	180.0	C7—C8—C9—C10	0.0
C1—C2—C3—O3	0.0	C7—C8—C9—N1	180.0
C1—C2—C3—C4	180.0	C8—C9—C10—C11	0.0
O3—C3—C4—C5	0.0	N1—C9—C10—C11	180.0
C2—C3—C4—C5	180.0	C9—C10—C11—C12	0.0
O3—C3—C4—C6	−120.58 (12)	C10—C11—C12—C7	0.0
C2—C3—C4—C6	59.42 (12)	C8—C7—C12—C11	0.0
O3—C3—C4—C6i	120.58 (12)	C1—C7—C12—C11	180.0
C2—C3—C4—C6i	−59.42 (12)	C10—C9—N1—O2	180.0
C2—C1—C7—C8	180.0	C8—C9—N1—O2	0.0
C2—C1—C7—C12	0.0	C10—C9—N1—O1	0.0
C12—C7—C8—C9	0.0	C8—C9—N1—O1	180.0
C1—C7—C8—C9	180.0

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ii	0.98	2.44	3.367 (2)	158
C10—H10···O2iii	0.95	2.50	3.366 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2i	0.98	2.44	3.367 (2)	158
C10—H10⋯O2ii	0.95	2.50	3.366 (3)	152

Symmetry codes: (i) ; (ii) .