(E)-1-(4-Nitro­phen­yl)-3-phenyl­prop-2-en-1-one

Jing, L.-H.

doi:10.1107/S1600536809037556

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2510

doi:10.1107/S1600536809037556

Open

access

(E)-1-(4-Nitrophenyl)-3-phenylprop-2-en-1-one

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jlhjhr@yahoo.com.cn

(Received 16 September 2009; accepted 16 September 2009; online 26 September 2009)

In the title compound, C₁₅H₁₁NO₃, the configuration of the keto group with respect to the olefinic double bond is s–cis. The two benzene rings form a dihedral angle of 5.00 (5)°. The molecules are linked into a two-dimensional network parallel to ( $[\overline{1}]$ 04) by C—H⋯O hydrogen bonds.

Related literature

For the biological activity of chalcone derivatives, see: Dimmock et al. (1999 ). For the synthesis, see: Cocconcelli et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₁NO₃
M_r = 253.25
Monoclinic, P 2₁ /c
a = 6.2139 (10) Å
b = 13.159 (2) Å
c = 14.450 (3) Å
β = 92.106 (3)°
V = 1180.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 93 K
0.50 × 0.18 × 0.18 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
9403 measured reflections
2687 independent reflections
2264 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.00
2687 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.95	2.47	3.3314 (15)	150
C5—H5⋯O3ⁱⁱ	0.95	2.56	3.4635 (16)	160
Symmetry codes: (i) -x, -y+1, -z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037556/ci2913sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037556/ci2913Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives are a class of important compounds that possess antiprotzoal, antihelmintic, amoebicidal, anti-ulcer, antiviral, insecticidal, antibacterial, anticancer, cytotoxic and immunosuppressive activities (Dimmock et al., 1999). The crystal structures of some chalcone derivatives have been reported. We report here the crystal structure of the title compound.

Bond lengths and angles in the title molecule are normal. The configuration of the keto group with respect to the olefinic double bond is typically s-cis, with a O1—C9—C8—C7 torsion angle of 0.5 (2)° (Fig. 1). The N1/O2/O3 and C10-C15 planes form a dihedral angle of 10.80 (11)°. The two benzene rings (C10-C15 and C1-C6) form a dihedral angle of 5.00 (5)°. The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1). The molecules are linked into a two-dimensional network parallel to the (1 0 4) by the above hydrogen bonds.

Related literature top

For biological activities of chalcone derivatives, see: Dimmock et al. (1999). For the synthesis, see: Cocconcelli et al. (2008).

Experimental top

The title compound was synthesized according to the method reported in the literature (Cocconcelli et al., 2008). Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of a acetone solution.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

(E)-1-(4-Nitrophenyl)-3-phenylprop-2-en-1-one top

Crystal data top

C₁₅H₁₁NO₃	F(000) = 528
M_r = 253.25	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3448 reflections
a = 6.2139 (10) Å	θ = 3.1–27.5°
b = 13.159 (2) Å	µ = 0.10 mm⁻¹
c = 14.450 (3) Å	T = 93 K
β = 92.106 (3)°	Needle, yellow
V = 1180.8 (3) Å³	0.50 × 0.18 × 0.18 mm
Z = 4

Data collection top

Rigaku SPIDER diffractometer	2264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −8→7
9403 measured reflections	k = −17→17
2687 independent reflections	l = −18→15

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0516P)² + 0.336P] where P = (F_o² + 2F_c²)/3
2687 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₁NO₃	V = 1180.8 (3) Å³
M_r = 253.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2139 (10) Å	µ = 0.10 mm⁻¹
b = 13.159 (2) Å	T = 93 K
c = 14.450 (3) Å	0.50 × 0.18 × 0.18 mm
β = 92.106 (3)°

Data collection top

Rigaku SPIDER diffractometer	2264 reflections with I > 2σ(I)
9403 measured reflections	R_int = 0.025
2687 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.00	Δρ_max = 0.36 e Å⁻³
2687 reflections	Δρ_min = −0.19 e Å⁻³
172 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.19885 (14)	0.39882 (7)	0.06264 (7)	0.0243 (2)
O2	0.89968 (15)	0.02961 (7)	0.20944 (7)	0.0266 (2)
O3	1.11753 (14)	0.14090 (7)	0.27163 (7)	0.0272 (2)
N1	0.94974 (16)	0.11770 (8)	0.22851 (7)	0.0185 (2)
C1	0.11212 (19)	0.77346 (9)	0.04561 (8)	0.0179 (3)
H1	−0.0164	0.7395	0.0258	0.021*
C2	0.1184 (2)	0.87899 (9)	0.04625 (9)	0.0209 (3)
H2	−0.0059	0.9169	0.0277	0.025*
C3	0.3061 (2)	0.92892 (9)	0.07402 (9)	0.0221 (3)
H3	0.3104	1.0011	0.0741	0.027*
C4	0.4885 (2)	0.87379 (9)	0.10183 (8)	0.0205 (3)
H4	0.6170	0.9083	0.1206	0.025*
C5	0.48224 (19)	0.76832 (9)	0.10203 (8)	0.0180 (3)
H5	0.6066	0.7309	0.1214	0.022*
C6	0.29377 (19)	0.71675 (9)	0.07389 (8)	0.0158 (3)
C7	0.27514 (19)	0.60597 (9)	0.07315 (8)	0.0163 (2)
H7	0.1469	0.5789	0.0451	0.020*
C8	0.41785 (19)	0.53830 (9)	0.10745 (8)	0.0169 (3)
H8	0.5496	0.5604	0.1362	0.020*
C9	0.36764 (19)	0.42863 (9)	0.10009 (8)	0.0167 (3)
C10	0.52508 (19)	0.35096 (9)	0.13838 (8)	0.0155 (2)
C11	0.72971 (19)	0.37564 (9)	0.17453 (8)	0.0173 (3)
H11	0.7733	0.4448	0.1780	0.021*
C12	0.87037 (19)	0.29959 (9)	0.20556 (8)	0.0172 (3)
H12	1.0095	0.3158	0.2308	0.021*
C13	0.80212 (19)	0.19972 (9)	0.19868 (8)	0.0158 (3)
C14	0.59903 (19)	0.17265 (9)	0.16446 (8)	0.0174 (3)
H14	0.5558	0.1034	0.1618	0.021*
C15	0.46102 (19)	0.24900 (9)	0.13438 (8)	0.0172 (3)
H15	0.3209	0.2322	0.1107	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0198 (5)	0.0168 (4)	0.0355 (5)	−0.0023 (4)	−0.0093 (4)	0.0018 (4)
O2	0.0289 (5)	0.0153 (4)	0.0349 (5)	0.0044 (4)	−0.0061 (4)	−0.0033 (4)
O3	0.0188 (5)	0.0252 (5)	0.0367 (6)	0.0010 (4)	−0.0095 (4)	0.0031 (4)
N1	0.0180 (5)	0.0183 (5)	0.0190 (5)	0.0018 (4)	0.0005 (4)	0.0008 (4)
C1	0.0174 (6)	0.0176 (6)	0.0184 (6)	−0.0015 (5)	−0.0016 (5)	0.0006 (5)
C2	0.0212 (6)	0.0174 (6)	0.0238 (6)	0.0029 (5)	−0.0032 (5)	0.0021 (5)
C3	0.0278 (7)	0.0132 (5)	0.0250 (6)	−0.0008 (5)	−0.0022 (5)	−0.0002 (5)
C4	0.0206 (6)	0.0186 (6)	0.0221 (6)	−0.0039 (5)	−0.0017 (5)	−0.0014 (5)
C5	0.0168 (6)	0.0190 (6)	0.0181 (6)	0.0007 (5)	−0.0004 (5)	0.0013 (5)
C6	0.0180 (6)	0.0158 (6)	0.0136 (5)	0.0005 (4)	0.0013 (4)	0.0001 (4)
C7	0.0164 (6)	0.0166 (6)	0.0160 (6)	−0.0012 (4)	0.0004 (4)	−0.0004 (4)
C8	0.0157 (6)	0.0161 (6)	0.0187 (6)	−0.0021 (4)	−0.0016 (5)	−0.0009 (4)
C9	0.0169 (6)	0.0161 (6)	0.0170 (6)	−0.0007 (5)	0.0003 (5)	0.0006 (4)
C10	0.0168 (6)	0.0148 (5)	0.0147 (6)	0.0006 (4)	0.0002 (4)	−0.0001 (4)
C11	0.0186 (6)	0.0142 (5)	0.0189 (6)	−0.0019 (5)	−0.0004 (5)	−0.0004 (4)
C12	0.0151 (6)	0.0182 (6)	0.0181 (6)	−0.0015 (4)	−0.0015 (5)	−0.0002 (4)
C13	0.0172 (6)	0.0160 (6)	0.0142 (5)	0.0033 (4)	0.0004 (4)	0.0006 (4)
C14	0.0211 (6)	0.0136 (5)	0.0176 (6)	−0.0007 (5)	−0.0010 (5)	−0.0008 (4)
C15	0.0160 (6)	0.0170 (6)	0.0183 (6)	−0.0018 (4)	−0.0024 (5)	0.0001 (4)

Geometric parameters (Å, º) top

O1—C9	1.2268 (15)	C7—C8	1.3389 (17)
O2—N1	1.2289 (14)	C7—H7	0.95
O3—N1	1.2331 (14)	C8—C9	1.4795 (16)
N1—C13	1.4708 (15)	C8—H8	0.95
C1—C2	1.3893 (17)	C9—C10	1.5060 (16)
C1—C6	1.4014 (17)	C10—C11	1.3951 (17)
C1—H1	0.95	C10—C15	1.4000 (16)
C2—C3	1.3851 (18)	C11—C12	1.3920 (17)
C2—H2	0.95	C11—H11	0.95
C3—C4	1.3923 (18)	C12—C13	1.3835 (17)
C3—H3	0.95	C12—H12	0.95
C4—C5	1.3885 (17)	C13—C14	1.3850 (17)
C4—H4	0.95	C14—C15	1.3808 (16)
C5—C6	1.4009 (17)	C14—H14	0.95
C5—H5	0.95	C15—H15	0.95
C6—C7	1.4624 (16)

O2—N1—O3	123.31 (10)	C7—C8—C9	119.15 (11)
O2—N1—C13	118.46 (10)	C7—C8—H8	120.4
O3—N1—C13	118.23 (10)	C9—C8—H8	120.4
C2—C1—C6	120.54 (11)	O1—C9—C8	121.21 (11)
C2—C1—H1	119.7	O1—C9—C10	118.58 (11)
C6—C1—H1	119.7	C8—C9—C10	120.21 (10)
C3—C2—C1	119.95 (11)	C11—C10—C15	119.50 (11)
C3—C2—H2	120.0	C11—C10—C9	123.39 (11)
C1—C2—H2	120.0	C15—C10—C9	117.09 (11)
C2—C3—C4	120.28 (11)	C12—C11—C10	120.40 (11)
C2—C3—H3	119.9	C12—C11—H11	119.8
C4—C3—H3	119.9	C10—C11—H11	119.8
C5—C4—C3	119.93 (11)	C13—C12—C11	118.21 (11)
C5—C4—H4	120.0	C13—C12—H12	120.9
C3—C4—H4	120.0	C11—C12—H12	120.9
C4—C5—C6	120.44 (11)	C12—C13—C14	122.88 (11)
C4—C5—H5	119.8	C12—C13—N1	119.33 (11)
C6—C5—H5	119.8	C14—C13—N1	117.79 (10)
C5—C6—C1	118.85 (11)	C15—C14—C13	118.19 (11)
C5—C6—C7	123.37 (11)	C15—C14—H14	120.9
C1—C6—C7	117.77 (11)	C13—C14—H14	120.9
C8—C7—C6	127.53 (11)	C14—C15—C10	120.80 (11)
C8—C7—H7	116.2	C14—C15—H15	119.6
C6—C7—H7	116.2	C10—C15—H15	119.6

C6—C1—C2—C3	0.74 (19)	C8—C9—C10—C15	175.96 (10)
C1—C2—C3—C4	−0.36 (19)	C15—C10—C11—C12	0.67 (18)
C2—C3—C4—C5	−0.20 (19)	C9—C10—C11—C12	−177.52 (11)
C3—C4—C5—C6	0.38 (18)	C10—C11—C12—C13	0.57 (18)
C4—C5—C6—C1	0.00 (18)	C11—C12—C13—C14	−1.58 (18)
C4—C5—C6—C7	−179.43 (11)	C11—C12—C13—N1	178.29 (10)
C2—C1—C6—C5	−0.56 (18)	O2—N1—C13—C12	−169.34 (11)
C2—C1—C6—C7	178.91 (11)	O3—N1—C13—C12	10.81 (16)
C5—C6—C7—C8	8.14 (19)	O2—N1—C13—C14	10.54 (16)
C1—C6—C7—C8	−171.29 (12)	O3—N1—C13—C14	−169.31 (11)
C6—C7—C8—C9	179.69 (11)	C12—C13—C14—C15	1.28 (18)
C7—C8—C9—O1	0.54 (18)	N1—C13—C14—C15	−178.59 (10)
C7—C8—C9—C10	−179.81 (11)	C13—C14—C15—C10	0.04 (17)
O1—C9—C10—C11	173.86 (12)	C11—C10—C15—C14	−0.99 (18)
C8—C9—C10—C11	−5.80 (17)	C9—C10—C15—C14	177.32 (11)
O1—C9—C10—C15	−4.38 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.95	2.47	3.3314 (15)	150
C5—H5···O3ⁱⁱ	0.95	2.56	3.4635 (16)	160

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₃
M_r	253.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	6.2139 (10), 13.159 (2), 14.450 (3)
β (°)	92.106 (3)
V (Å³)	1180.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.50 × 0.18 × 0.18

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9403, 2687, 2264
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.00
No. of reflections	2687
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.19

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.95	2.47	3.3314 (15)	150
C5—H5···O3ⁱⁱ	0.95	2.56	3.4635 (16)	160

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, y+1/2, −z+1/2.

Acknowledgements

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Cocconcelli, G., Diodato, E., Caricasole, A., Gaviraghi, G., Genesio, E., Ghiron, C., Magnoni, L., Pecchioli, E., Plazzi, P. V. & Terstappen, G. C. (2008). Bioorg. Med. Chem. 16, 2043–2052. Web of Science CrossRef PubMed CAS Google Scholar
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149. Web of Science PubMed CAS Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar