3-(4-Methoxy­phen­yl)-1-(2-nitrophen­yl)prop-2-en-1-one

Guo, H.-M.; Liu, L.-Q.; Yang, J.; Jian, F.-F.

doi:10.1107/S1600536809048120

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3117

doi:10.1107/S1600536809048120

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3-(4-Methoxyphenyl)-1-(2-nitrophenyl)prop-2-en-1-one

Huan-Mei Guo,^a Le-Qing Liu,^b Jie Yang ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute , Weifang University, Weifang 261061, People's Republic of China, and ^bthe Seventh Middle School of Wei Fang, Weifang 261041, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 8 October 2009; accepted 13 November 2009; online 18 November 2009)

The title compound, C₁₆H₁₃NO₄, was prepared from 2-nitrylhypnone [systematic name: 1-(2-nitrophenyl)ethanone] and 4-methoxybenzophenone by a Claisen–Schmidt condensation. The dihedral angle formed by the two benzene rings is 80.73 (2). The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological activity of chalcones, see: Anto et al. (1994 ); De Vincenzo et al. (2000 ); Dimmock et al. (1998 ); Hsieh et al. (1998 ). For a related structure, see: Fun et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₃NO₄
M_r = 283.27
Monoclinic, P 2₁ /c
a = 11.594 (2) Å
b = 7.7736 (16) Å
c = 15.174 (3) Å
β = 94.59 (3)°
V = 1363.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.21 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
12773 measured reflections
3107 independent reflections
2667 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.124
S = 1.08
3107 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O1ⁱ	0.93	2.51	3.249 (1)	136
C14—H14A⋯O3ⁱⁱ	0.93	2.59	3.259 (2)	129
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048120/fl2279sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048120/fl2279Isup2.hkl

checkCIF report

Comment top

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al.,1998)and antioxidant (Anto et al.,1994). Of particular interest, the effectiveness of chalcones againest cancer has been investigated (De Vincenzo et al., 2000; Dimmock et al.,1998). As part of our search for new biologically active compounds we synthesized the title compound(I) and report its crystal structure herein.

Scheme I

The molecule (I) (Fig. 1) is made up of two essentially planar segments. The atoms O1, C1,C2, C3, C4, C5, C6 and C7 make up one segment (largest deviation being 0.018Å for C6) with the nitro phenyl group being the second planar segment (largest deviation 0.0177Å for N1).The dihedral angel formed by the two planes is 81.07 (2)°. All of the bond lengths and bond angles are in normal ranges and comparable to those found in a related structure (Fun et al., 2008). In the crystal structure, the molecules are stacked along the b axis and linked via C—H···O interactions (Fig. 2).

Related literature top

For the biological activity of chalcones, see: Anto et al. (1994); De Vincenzo et al. (2000); Dimmock et al. (1998); Hsieh et al. (1998).For a related structure, see: Fun et al. (2008);

Experimental top

The title compound(I) was prepared by the process as following: A mixture of the 2-nitrylhypnone (0.02 mol), 4-methoxybenzophenone(0.02 mol) and 10%NaOH(10 ml) was stirred in ethanol(30 ml) for 3 h to afford the title compound(yield78%).Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound,viewed along a axis.

3-(4-Methoxyphenyl)-1-(2-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₃NO₄	F(000) = 592
M_r = 283.27	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2667 reflections
a = 11.594 (2) Å	θ = 3.1–27.5°
b = 7.7736 (16) Å	µ = 0.10 mm⁻¹
c = 15.174 (3) Å	T = 293 K
β = 94.59 (3)°	Bar, yellow
V = 1363.1 (5) Å³	0.21 × 0.18 × 0.10 mm
Z = 4

Data collection top

Bruker sMART CCD area-detector diffractometer	2667 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.018
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
phi and ω scans	h = −15→15
12773 measured reflections	k = −10→8
3107 independent reflections	l = −19→19

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0747P)² + 0.157P] where P = (F_o² + 2F_c²)/3
3107 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₃NO₄	V = 1363.1 (5) Å³
M_r = 283.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.594 (2) Å	µ = 0.10 mm⁻¹
b = 7.7736 (16) Å	T = 293 K
c = 15.174 (3) Å	0.21 × 0.18 × 0.10 mm
β = 94.59 (3)°

Data collection top

Bruker sMART CCD area-detector diffractometer	2667 reflections with I > 2σ(I)
12773 measured reflections	R_int = 0.018
3107 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.08	Δρ_max = 0.19 e Å⁻³
3107 reflections	Δρ_min = −0.22 e Å⁻³
190 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
C8	0.72395 (9)	0.18277 (14)	0.22201 (7)	0.0385 (2)
H8A	0.7810	0.2655	0.2340	0.046*
O4	0.82958 (9)	0.02414 (13)	0.02294 (6)	0.0603 (3)
C5	0.63411 (9)	0.17369 (13)	0.28408 (7)	0.0371 (2)
N1	1.07316 (9)	0.10395 (13)	0.16402 (6)	0.0447 (2)
C2	0.46388 (9)	0.17332 (14)	0.40548 (8)	0.0402 (3)
C7	0.44279 (10)	0.09466 (16)	0.32265 (8)	0.0482 (3)
H7A	0.3714	0.0436	0.3073	0.058*
O3	1.01265 (9)	−0.02297 (12)	0.16921 (7)	0.0611 (3)
C16	0.85299 (10)	0.42736 (15)	0.08146 (8)	0.0442 (3)
H16A	0.7755	0.4334	0.0604	0.053*
C11	0.90152 (9)	0.26829 (14)	0.10358 (7)	0.0359 (2)
C12	1.01784 (9)	0.26616 (13)	0.13472 (7)	0.0362 (2)
C6	0.52710 (10)	0.09263 (15)	0.26394 (8)	0.0445 (3)
H6A	0.5130	0.0366	0.2100	0.053*
C13	1.08378 (10)	0.41407 (16)	0.14300 (8)	0.0454 (3)
H13A	1.1615	0.4087	0.1636	0.054*
C9	0.73401 (10)	0.08635 (15)	0.15007 (8)	0.0435 (3)
H9A	0.6811	−0.0023	0.1384	0.052*
C14	1.03253 (12)	0.57038 (15)	0.12026 (9)	0.0514 (3)
H14A	1.0760	0.6710	0.1254	0.062*
C4	0.65192 (9)	0.25538 (14)	0.36590 (8)	0.0414 (3)
H4A	0.7213	0.3129	0.3799	0.050*
O2	1.17769 (9)	0.10328 (15)	0.18354 (8)	0.0719 (3)
C10	0.82364 (10)	0.11242 (15)	0.08857 (7)	0.0409 (3)
C15	0.91755 (12)	0.57743 (15)	0.09011 (9)	0.0493 (3)
H15A	0.8831	0.6828	0.0755	0.059*
C3	0.56915 (10)	0.25320 (14)	0.42687 (8)	0.0410 (3)
H3A	0.5842	0.3051	0.4818	0.049*
O1	0.37527 (8)	0.16582 (14)	0.45895 (6)	0.0582 (3)
C1	0.39013 (13)	0.24330 (19)	0.54405 (9)	0.0596 (4)
H1A	0.3210	0.2283	0.5740	0.089*
H1B	0.4054	0.3639	0.5378	0.089*
H1C	0.4540	0.1900	0.5778	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.0357 (5)	0.0373 (5)	0.0419 (5)	−0.0036 (4)	−0.0006 (4)	0.0031 (4)
O4	0.0715 (6)	0.0603 (6)	0.0498 (5)	−0.0125 (5)	0.0103 (4)	−0.0185 (4)
C5	0.0369 (5)	0.0338 (5)	0.0400 (5)	−0.0028 (4)	0.0002 (4)	0.0032 (4)
N1	0.0496 (5)	0.0450 (5)	0.0397 (5)	0.0120 (4)	0.0042 (4)	−0.0005 (4)
C2	0.0387 (5)	0.0357 (5)	0.0467 (6)	−0.0029 (4)	0.0060 (4)	0.0029 (4)
C7	0.0404 (6)	0.0522 (7)	0.0516 (7)	−0.0158 (5)	0.0010 (5)	−0.0042 (5)
O3	0.0728 (6)	0.0398 (5)	0.0711 (6)	0.0075 (4)	0.0090 (5)	0.0099 (4)
C16	0.0426 (6)	0.0422 (6)	0.0481 (6)	0.0065 (4)	0.0056 (5)	0.0045 (5)
C11	0.0386 (5)	0.0361 (5)	0.0338 (5)	0.0004 (4)	0.0068 (4)	−0.0003 (4)
C12	0.0396 (5)	0.0365 (5)	0.0330 (5)	0.0047 (4)	0.0061 (4)	−0.0024 (4)
C6	0.0438 (6)	0.0472 (6)	0.0419 (6)	−0.0112 (5)	−0.0004 (5)	−0.0041 (5)
C13	0.0394 (5)	0.0485 (7)	0.0487 (6)	−0.0032 (5)	0.0060 (5)	−0.0088 (5)
C9	0.0432 (6)	0.0406 (6)	0.0466 (6)	−0.0093 (4)	0.0018 (5)	−0.0011 (5)
C14	0.0590 (7)	0.0378 (6)	0.0590 (7)	−0.0104 (5)	0.0145 (6)	−0.0077 (5)
C4	0.0349 (5)	0.0418 (6)	0.0467 (6)	−0.0067 (4)	−0.0012 (4)	−0.0029 (5)
O2	0.0501 (6)	0.0756 (7)	0.0877 (8)	0.0208 (5)	−0.0089 (5)	0.0045 (6)
C10	0.0440 (6)	0.0387 (6)	0.0396 (5)	−0.0008 (4)	0.0007 (4)	−0.0014 (4)
C15	0.0618 (7)	0.0337 (6)	0.0537 (7)	0.0077 (5)	0.0134 (6)	0.0041 (5)
C3	0.0406 (6)	0.0400 (6)	0.0417 (5)	−0.0026 (4)	−0.0006 (4)	−0.0044 (4)
O1	0.0492 (5)	0.0682 (6)	0.0593 (5)	−0.0160 (4)	0.0177 (4)	−0.0100 (5)
C1	0.0642 (8)	0.0620 (8)	0.0548 (7)	0.0018 (6)	0.0188 (6)	−0.0020 (6)

Geometric parameters (Å, º) top

C8—C9	1.3369 (17)	C11—C10	1.5174 (15)
C8—C5	1.4609 (16)	C12—C13	1.3809 (16)
C8—H8A	0.9300	C6—H6A	0.9300
O4—C10	1.2159 (15)	C13—C14	1.3841 (18)
C5—C4	1.3951 (16)	C13—H13A	0.9300
C5—C6	1.4031 (15)	C9—C10	1.4653 (17)
N1—O3	1.2168 (14)	C9—H9A	0.9300
N1—O2	1.2242 (15)	C14—C15	1.3753 (19)
N1—C12	1.4674 (14)	C14—H14A	0.9300
C2—O1	1.3604 (14)	C4—C3	1.3854 (17)
C2—C3	1.3846 (16)	C4—H4A	0.9300
C2—C7	1.4015 (17)	C15—H15A	0.9300
C7—C6	1.3743 (18)	C3—H3A	0.9300
C7—H7A	0.9300	O1—C1	1.4227 (17)
C16—C15	1.3866 (18)	C1—H1A	0.9600
C16—C11	1.3885 (15)	C1—H1B	0.9600
C16—H16A	0.9300	C1—H1C	0.9600
C11—C12	1.3929 (15)

C9—C8—C5	127.78 (10)	C12—C13—H13A	120.5
C9—C8—H8A	116.1	C14—C13—H13A	120.5
C5—C8—H8A	116.1	C8—C9—C10	123.72 (10)
C4—C5—C6	117.62 (10)	C8—C9—H9A	118.1
C4—C5—C8	119.30 (9)	C10—C9—H9A	118.1
C6—C5—C8	123.02 (10)	C15—C14—C13	120.22 (11)
O3—N1—O2	123.06 (11)	C15—C14—H14A	119.9
O3—N1—C12	118.43 (10)	C13—C14—H14A	119.9
O2—N1—C12	118.50 (11)	C3—C4—C5	121.84 (10)
O1—C2—C3	124.96 (11)	C3—C4—H4A	119.1
O1—C2—C7	115.49 (10)	C5—C4—H4A	119.1
C3—C2—C7	119.55 (11)	O4—C10—C9	122.22 (11)
C6—C7—C2	120.28 (10)	O4—C10—C11	120.10 (11)
C6—C7—H7A	119.9	C9—C10—C11	117.30 (9)
C2—C7—H7A	119.9	C14—C15—C16	119.96 (11)
C15—C16—C11	121.41 (11)	C14—C15—H15A	120.0
C15—C16—H16A	119.3	C16—C15—H15A	120.0
C11—C16—H16A	119.3	C2—C3—C4	119.58 (10)
C16—C11—C12	117.07 (10)	C2—C3—H3A	120.2
C16—C11—C10	116.75 (10)	C4—C3—H3A	120.2
C12—C11—C10	126.14 (9)	C2—O1—C1	118.75 (10)
C13—C12—C11	122.33 (10)	O1—C1—H1A	109.5
C13—C12—N1	117.55 (10)	O1—C1—H1B	109.5
C11—C12—N1	120.05 (10)	H1A—C1—H1B	109.5
C7—C6—C5	121.06 (11)	O1—C1—H1C	109.5
C7—C6—H6A	119.5	H1A—C1—H1C	109.5
C5—C6—H6A	119.5	H1B—C1—H1C	109.5
C12—C13—C14	119.00 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O1ⁱ	0.93	2.51	3.249 (1)	136
C14—H14A···O3ⁱⁱ	0.93	2.59	3.259 (2)	129

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₄
M_r	283.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.594 (2), 7.7736 (16), 15.174 (3)
β (°)	94.59 (3)
V (Å³)	1363.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.21 × 0.18 × 0.10

Data collection
Diffractometer	Bruker sMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12773, 3107, 2667
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.124, 1.08
No. of reflections	3107
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O1ⁱ	0.93	2.51	3.249 (1)	136
C14—H14A···O3ⁱⁱ	0.93	2.59	3.259 (2)	129

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

Acknowledgements

The authors would like to thank the National Natural Science Foundation of Shandong Province (Y2008B29) and the Yuandu Scholar Fund of Weifang City for support.

References

Anto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr. 17, 73–80. CrossRef CAS Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
De Vincenzo, R., Ferlini, C. & Distefano, M. (2000). Cancer Chemother. Pharmacol. 46, 305–312. Web of Science CrossRef PubMed CAS Google Scholar
Dimmock, J. R., Kandepu, N. M. & Hetherington, M. (1998). J. Med. Chem. 41, 1014–1026. Web of Science CSD CrossRef CAS PubMed Google Scholar
Fun, H.-K., Chantrapromma, S., Patil, P. S., D'Silva, E. D. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o954–o955. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res. 15, 39–46. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar