3-(4-Methoxy-phen-yl)-1-(2-nitrophen-yl)prop-2-en-1-one.

The title compound, C(16)H(13)NO(4), was prepared from 2-nitrylhypnone [systematic name: 1-(2-nitrophenyl)ethanone] and 4-methoxy-benzophenone by a Claisen-Schmidt condensation. The dihedral angle formed by the two benzene rings is 80.73 (2). The crystal packing is stabilized by inter-molecular 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 = 283.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.08

3107 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

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.

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

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

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

C16H13NO4	F(000) = 592
Mr = 283.27	Dx = 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

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

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(Fo2) + (0.0747P)2 + 0.157P] where P = (Fo2 + 2Fc2)/3
3107 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.22 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
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*

	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)

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)

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

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) ; (ii) .