(1E,4E)-1-(3-Nitro-phen-yl)-5-phenyl-penta-1,4-dien-3-one.

In the title compound, C(17)H(13)NO(3), the dihedral angle between the benzene rings is 31.21 (5)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds occur. A C-H⋯π inter-action is also indicated.

Related literature

For the pharmacological importance of chalcones and bis­ chalcones, see: Sarojini et al. (2006 ▶); Dhar (1981 ▶); Dimmock et al. (1999 ▶); Satyanarayana et al. (2004 ▶). For our work on synthesis of different derivatives of chalcones, see: Baktır et al. (2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Samshuddin et al. (2011a ▶,b ▶,c ▶). For related structures, see: Butcher et al. (2006a ▶,b ▶; 2007a ▶,b ▶,c ▶); Harrison et al. (2006 ▶); Hu et al. (2004 ▶); Fischer et al. (2007 ▶); Patil et al. (2007 ▶); Zhao et al. (2007 ▶).

Experimental

Crystal data

C17H13NO3

M = 279.28

Monoclinic,

a = 11.9806 (6) Å

b = 9.8955 (4) Å

c = 12.5562 (7) Å

β = 114.992 (7)°

V = 1349.21 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.44 × 0.34 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.969, T max = 1.000

7835 measured reflections

3746 independent reflections

2453 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.128

S = 1.02

3746 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST (Nardelli, 1983 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052548/tk5031sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052548/tk5031Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052548/tk5031Isup3.cml

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

C17H13NO3	F(000) = 584
Mr = 279.28	Dx = 1.375 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2209 reflections
a = 11.9806 (6) Å	θ = 3.1–30.9°
b = 9.8955 (4) Å	µ = 0.10 mm−1
c = 12.5562 (7) Å	T = 293 K
β = 114.992 (7)°	Plate, colourless
V = 1349.21 (14) Å3	0.44 × 0.34 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3746 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2453 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 10.5081 pixels mm-1	θmax = 30.9°, θmin = 3.3°
ω scans	h = −17→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −13→14
Tmin = 0.969, Tmax = 1.000	l = −11→18
7835 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.047P)2 + 0.2703P] where P = (Fo2 + 2Fc2)/3
3746 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.17385 (11)	0.14120 (12)	0.04941 (10)	0.0346 (4)
O2	0.11627 (15)	0.33639 (14)	−0.03094 (11)	0.0526 (5)
O3	0.54296 (11)	0.04578 (11)	0.67363 (10)	0.0288 (4)
N1	0.16833 (13)	0.26465 (15)	0.05501 (12)	0.0291 (4)
C1	0.34756 (14)	0.30928 (16)	0.37830 (13)	0.0208 (4)
C2	0.29603 (14)	0.25023 (16)	0.26714 (13)	0.0211 (4)
C3	0.22682 (14)	0.32911 (16)	0.17068 (13)	0.0226 (5)
C4	0.20852 (15)	0.46592 (17)	0.17935 (14)	0.0248 (5)
C5	0.26174 (15)	0.52505 (17)	0.28955 (14)	0.0247 (5)
C6	0.32965 (15)	0.44777 (16)	0.38746 (14)	0.0242 (5)
C7	0.41680 (14)	0.22370 (16)	0.48051 (14)	0.0225 (5)
C8	0.46170 (14)	0.26055 (16)	0.59296 (14)	0.0227 (5)
C9	0.53494 (14)	0.16722 (16)	0.68958 (14)	0.0225 (5)
C10	0.60212 (14)	0.23207 (16)	0.80546 (13)	0.0221 (5)
C11	0.70265 (14)	0.17661 (16)	0.88844 (13)	0.0226 (5)
C12	0.78098 (14)	0.23472 (16)	1.00356 (13)	0.0211 (4)
C13	0.74719 (15)	0.34930 (17)	1.04775 (14)	0.0256 (5)
C14	0.82268 (16)	0.39866 (17)	1.15834 (15)	0.0296 (5)
C15	0.93264 (16)	0.33433 (18)	1.22672 (15)	0.0307 (5)
C16	0.96719 (15)	0.22128 (18)	1.18395 (15)	0.0288 (5)
C17	0.89256 (15)	0.17173 (17)	1.07295 (14)	0.0258 (5)
H2A	0.30800	0.15890	0.25790	0.0250*
H4A	0.16180	0.51670	0.11310	0.0300*
H5A	0.25180	0.61710	0.29780	0.0300*
H6A	0.36420	0.48870	0.46100	0.0290*
H7A	0.43070	0.13480	0.46530	0.0270*
H8A	0.44660	0.34770	0.61140	0.0270*
H10A	0.57350	0.31380	0.82090	0.0260*
H11A	0.72550	0.09230	0.87160	0.0270*
H13A	0.67340	0.39290	1.00270	0.0310*
H14A	0.79940	0.47530	1.18680	0.0360*
H15A	0.98280	0.36730	1.30110	0.0370*
H16A	1.04090	0.17790	1.22970	0.0350*
H17A	0.91710	0.09590	1.04460	0.0310*

	U11	U22	U33	U12	U13	U23
O1	0.0408 (8)	0.0265 (6)	0.0284 (7)	−0.0001 (6)	0.0068 (6)	−0.0062 (6)
O2	0.0800 (11)	0.0377 (8)	0.0184 (7)	−0.0015 (8)	−0.0003 (7)	0.0065 (6)
O3	0.0347 (7)	0.0216 (6)	0.0241 (6)	0.0027 (5)	0.0066 (5)	−0.0001 (5)
N1	0.0322 (8)	0.0298 (8)	0.0206 (7)	−0.0031 (7)	0.0066 (6)	−0.0004 (7)
C1	0.0195 (7)	0.0224 (8)	0.0202 (8)	0.0009 (6)	0.0082 (7)	0.0004 (7)
C2	0.0216 (7)	0.0183 (7)	0.0243 (8)	0.0010 (6)	0.0107 (7)	0.0001 (7)
C3	0.0240 (8)	0.0249 (8)	0.0171 (8)	−0.0039 (7)	0.0070 (7)	−0.0009 (7)
C4	0.0270 (8)	0.0251 (8)	0.0211 (8)	0.0029 (7)	0.0091 (7)	0.0067 (7)
C5	0.0307 (9)	0.0199 (8)	0.0270 (9)	0.0024 (7)	0.0156 (7)	0.0023 (7)
C6	0.0278 (8)	0.0259 (8)	0.0199 (8)	−0.0011 (7)	0.0112 (7)	−0.0032 (7)
C7	0.0216 (8)	0.0207 (8)	0.0226 (8)	0.0013 (7)	0.0068 (7)	−0.0001 (7)
C8	0.0228 (8)	0.0211 (8)	0.0230 (8)	0.0016 (7)	0.0085 (7)	−0.0001 (7)
C9	0.0204 (8)	0.0240 (8)	0.0222 (8)	−0.0003 (7)	0.0081 (7)	0.0012 (7)
C10	0.0253 (8)	0.0207 (8)	0.0192 (8)	0.0012 (7)	0.0084 (7)	0.0014 (7)
C11	0.0268 (8)	0.0206 (8)	0.0215 (8)	−0.0006 (7)	0.0112 (7)	0.0010 (7)
C12	0.0223 (8)	0.0227 (8)	0.0177 (7)	−0.0028 (7)	0.0079 (7)	0.0029 (7)
C13	0.0239 (8)	0.0259 (8)	0.0238 (8)	−0.0001 (7)	0.0071 (7)	0.0027 (7)
C14	0.0334 (9)	0.0262 (9)	0.0274 (9)	−0.0039 (8)	0.0111 (8)	−0.0043 (8)
C15	0.0310 (9)	0.0338 (10)	0.0223 (9)	−0.0092 (8)	0.0064 (8)	−0.0038 (8)
C16	0.0209 (8)	0.0352 (10)	0.0253 (9)	−0.0005 (7)	0.0050 (7)	0.0049 (8)
C17	0.0251 (8)	0.0264 (8)	0.0255 (8)	0.0006 (7)	0.0104 (7)	0.0010 (7)

O1—N1	1.2270 (19)	C13—C14	1.387 (2)
O2—N1	1.2202 (19)	C14—C15	1.386 (3)
O3—C9	1.2287 (19)	C15—C16	1.378 (3)
N1—C3	1.465 (2)	C16—C17	1.389 (2)
C1—C2	1.394 (2)	C2—H2A	0.9300
C1—C6	1.399 (2)	C4—H4A	0.9300
C1—C7	1.467 (2)	C5—H5A	0.9300
C2—C3	1.384 (2)	C6—H6A	0.9300
C3—C4	1.383 (2)	C7—H7A	0.9300
C4—C5	1.385 (2)	C8—H8A	0.9300
C5—C6	1.383 (2)	C10—H10A	0.9300
C7—C8	1.332 (2)	C11—H11A	0.9300
C8—C9	1.482 (2)	C13—H13A	0.9300
C9—C10	1.479 (2)	C14—H14A	0.9300
C10—C11	1.333 (2)	C15—H15A	0.9300
C11—C12	1.468 (2)	C16—H16A	0.9300
C12—C13	1.395 (2)	C17—H17A	0.9300
C12—C17	1.397 (2)
O1—N1—O2	123.25 (14)	C12—C17—C16	120.61 (16)
O1—N1—C3	118.38 (13)	C1—C2—H2A	120.00
O2—N1—C3	118.36 (14)	C3—C2—H2A	120.00
C2—C1—C6	118.32 (14)	C3—C4—H4A	121.00
C2—C1—C7	118.78 (14)	C5—C4—H4A	121.00
C6—C1—C7	122.89 (14)	C4—C5—H5A	120.00
C1—C2—C3	119.22 (15)	C6—C5—H5A	120.00
N1—C3—C2	118.73 (14)	C1—C6—H6A	119.00
N1—C3—C4	118.61 (14)	C5—C6—H6A	119.00
C2—C3—C4	122.65 (14)	C1—C7—H7A	117.00
C3—C4—C5	118.09 (15)	C8—C7—H7A	117.00
C4—C5—C6	120.27 (15)	C7—C8—H8A	119.00
C1—C6—C5	121.43 (15)	C9—C8—H8A	119.00
C1—C7—C8	126.52 (15)	C9—C10—H10A	119.00
C7—C8—C9	122.11 (15)	C11—C10—H10A	119.00
O3—C9—C8	122.43 (14)	C10—C11—H11A	117.00
O3—C9—C10	122.50 (15)	C12—C11—H11A	117.00
C8—C9—C10	115.02 (14)	C12—C13—H13A	120.00
C9—C10—C11	121.79 (15)	C14—C13—H13A	120.00
C10—C11—C12	126.80 (15)	C13—C14—H14A	120.00
C11—C12—C13	122.53 (15)	C15—C14—H14A	120.00
C11—C12—C17	118.99 (15)	C14—C15—H15A	120.00
C13—C12—C17	118.46 (14)	C16—C15—H15A	120.00
C12—C13—C14	120.55 (16)	C15—C16—H16A	120.00
C13—C14—C15	120.36 (16)	C17—C16—H16A	120.00
C14—C15—C16	119.65 (16)	C12—C17—H17A	120.00
C15—C16—C17	120.37 (17)	C16—C17—H17A	120.00
O1—N1—C3—C2	6.3 (3)	C1—C7—C8—C9	−177.47 (17)
O1—N1—C3—C4	−172.40 (17)	C7—C8—C9—O3	−11.3 (3)
O2—N1—C3—C2	−173.88 (18)	C7—C8—C9—C10	166.11 (17)
O2—N1—C3—C4	7.4 (3)	O3—C9—C10—C11	21.9 (3)
C6—C1—C2—C3	−1.6 (3)	C8—C9—C10—C11	−155.48 (17)
C7—C1—C2—C3	177.69 (17)	C9—C10—C11—C12	176.13 (16)
C2—C1—C6—C5	0.6 (3)	C10—C11—C12—C13	10.4 (3)
C7—C1—C6—C5	−178.66 (18)	C10—C11—C12—C17	−170.91 (18)
C2—C1—C7—C8	−173.22 (18)	C11—C12—C13—C14	178.32 (17)
C6—C1—C7—C8	6.1 (3)	C17—C12—C13—C14	−0.3 (3)
C1—C2—C3—N1	−177.19 (16)	C11—C12—C17—C16	−177.90 (16)
C1—C2—C3—C4	1.5 (3)	C13—C12—C17—C16	0.8 (3)
N1—C3—C4—C5	178.43 (17)	C12—C13—C14—C15	−0.3 (3)
C2—C3—C4—C5	−0.2 (3)	C13—C14—C15—C16	0.4 (3)
C3—C4—C5—C6	−0.8 (3)	C14—C15—C16—C17	0.0 (3)
C4—C5—C6—C1	0.6 (3)	C15—C16—C17—C12	−0.7 (3)

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3i	0.93	2.59	3.412 (2)	147
C7—H7A···O3	0.93	2.54	2.858 (2)	100
C11—H11A···O3	0.93	2.57	2.8724 (19)	100
C5—H5A···Cg1ii	0.93	2.62	3.3915 (19)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O3i	0.93	2.59	3.412 (2)	147
C5—H5A⋯Cg1ii	0.93	2.62	3.3915 (19)	141

Symmetry codes: (i) ; (ii) .