(E)-1-(4-Nitro-phen-yl)-3-phenyl-prop-2-en-1-one.

In the title compound, C(15)H(11)NO(3), 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 mol-ecules are linked into a two-dimensional network parallel to (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 = 253.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.00

2687 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

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

C15H11NO3	F(000) = 528
Mr = 253.25	Dx = 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

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

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(Fo2) + (0.0516P)2 + 0.336P] where P = (Fo2 + 2Fc2)/3
2687 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.19 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
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*

	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)

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)

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

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) ; (ii) .