(2E)-1-(2,5-Dimeth-oxy-phen-yl)-3-(3-nitro-phen-yl)prop-2-en-1-one.

In the title compound, C(17)H(15)NO(5), an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The benzene rings form a dihedral angle of 6.45 (7)° with each other. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(8) loops. Adjacent dimers are further connected by C-H⋯O hydrogen bonds into an infinite chain along the [011] direction.

Related literature

For biological activities of chalcones, see: Dimmock et al. (1999 ▶). For the structures of chalcone derivatives, see: Samshuddin et al. (2010 ▶); Fun et al. (2010a ▶,b ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011a ▶,b ▶). For related crystal structures, see: Jasinski et al. (2008 ▶); Sarojini et al. (2007 ▶); Ma (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H15NO5

M = 313.30

Triclinic,

a = 7.5015 (5) Å

b = 7.9962 (5) Å

c = 13.2468 (8) Å

α = 86.507 (1)°

β = 80.342 (1)°

γ = 76.332 (1)°

V = 760.96 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.41 × 0.38 × 0.13 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.987

16631 measured reflections

4381 independent reflections

3195 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.179

S = 1.02

4381 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043224/is2794sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043224/is2794Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043224/is2794Isup3.cml

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

C17H15NO5	Z = 2
Mr = 313.30	F(000) = 328
Triclinic, P1	Dx = 1.367 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5015 (5) Å	Cell parameters from 5160 reflections
b = 7.9962 (5) Å	θ = 2.6–32.3°
c = 13.2468 (8) Å	µ = 0.10 mm−1
α = 86.507 (1)°	T = 296 K
β = 80.342 (1)°	Block, yellow
γ = 76.332 (1)°	0.41 × 0.38 × 0.13 mm
V = 760.96 (8) Å3

Bruker APEX DUO CCD area-detector diffractometer	4381 independent reflections
Radiation source: fine-focus sealed tube	3195 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.960, Tmax = 0.987	k = −11→11
16631 measured reflections	l = −18→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1091P)2 + 0.0754P] where P = (Fo2 + 2Fc2)/3
4381 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.25 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
O1	0.15506 (16)	0.16718 (11)	0.39750 (8)	0.0591 (3)
O2	0.11277 (18)	−0.21224 (13)	0.07147 (7)	0.0671 (3)
O3	0.3565 (2)	−0.36287 (12)	0.39765 (9)	0.0802 (4)
O4	0.2174 (3)	0.37169 (16)	0.74170 (13)	0.0989 (5)
O5	0.3301 (3)	0.3286 (2)	0.88284 (13)	0.1121 (6)
N1	0.2941 (2)	0.2780 (2)	0.80490 (12)	0.0729 (4)
C1	0.14468 (17)	0.07338 (14)	0.31743 (9)	0.0409 (3)
C2	0.07436 (19)	0.15014 (15)	0.23001 (10)	0.0487 (3)
H2A	0.0312	0.2690	0.2265	0.058*
C3	0.0682 (2)	0.05257 (17)	0.14937 (10)	0.0502 (3)
H3A	0.0228	0.1057	0.0914	0.060*
C4	0.12955 (19)	−0.12516 (16)	0.15424 (9)	0.0458 (3)
C5	0.19828 (17)	−0.20273 (14)	0.23995 (9)	0.0419 (3)
H5A	0.2391	−0.3219	0.2429	0.050*
C6	0.20797 (16)	−0.10584 (13)	0.32289 (8)	0.0381 (2)
C7	0.29087 (19)	−0.20926 (14)	0.40881 (9)	0.0452 (3)
C8	0.2943 (2)	−0.12935 (16)	0.50575 (9)	0.0497 (3)
H8A	0.2364	−0.0137	0.5148	0.060*
C9	0.37566 (19)	−0.21468 (15)	0.57977 (9)	0.0460 (3)
H9A	0.4334	−0.3300	0.5689	0.055*
C10	0.38354 (17)	−0.14415 (15)	0.67833 (8)	0.0419 (3)
C11	0.33505 (18)	0.03198 (16)	0.69527 (9)	0.0455 (3)
H11A	0.2967	0.1094	0.6436	0.055*
C12	0.34453 (19)	0.09026 (18)	0.78952 (10)	0.0522 (3)
C13	0.3995 (2)	−0.0188 (2)	0.86864 (11)	0.0644 (4)
H13A	0.4044	0.0240	0.9316	0.077*
C14	0.4467 (2)	−0.1924 (2)	0.85189 (11)	0.0685 (4)
H14A	0.4839	−0.2685	0.9044	0.082*
C15	0.4399 (2)	−0.25623 (18)	0.75773 (10)	0.0542 (3)
H15A	0.4732	−0.3743	0.7476	0.065*
C16	0.0965 (3)	0.34867 (17)	0.39303 (15)	0.0703 (5)
H16A	0.1164	0.3956	0.4541	0.105*
H16B	−0.0333	0.3808	0.3876	0.105*
H16C	0.1665	0.3928	0.3344	0.105*
C17	0.1863 (3)	−0.3918 (2)	0.07001 (13)	0.0749 (5)
H17A	0.1741	−0.4357	0.0063	0.112*
H17B	0.1195	−0.4461	0.1256	0.112*
H17C	0.3152	−0.4158	0.0772	0.112*

	U11	U22	U33	U12	U13	U23
O1	0.0856 (7)	0.0345 (4)	0.0589 (6)	−0.0060 (4)	−0.0224 (5)	−0.0149 (4)
O2	0.0998 (9)	0.0582 (6)	0.0452 (5)	−0.0064 (5)	−0.0298 (5)	−0.0119 (4)
O3	0.1363 (12)	0.0367 (5)	0.0692 (7)	0.0086 (6)	−0.0573 (7)	−0.0125 (4)
O4	0.1368 (14)	0.0526 (7)	0.1063 (11)	−0.0103 (8)	−0.0283 (10)	−0.0141 (7)
O5	0.1285 (13)	0.1081 (11)	0.1059 (11)	−0.0205 (10)	−0.0210 (10)	−0.0706 (9)
N1	0.0739 (9)	0.0682 (8)	0.0789 (9)	−0.0184 (7)	−0.0019 (7)	−0.0394 (7)
C1	0.0446 (6)	0.0331 (5)	0.0452 (6)	−0.0076 (4)	−0.0069 (4)	−0.0070 (4)
C2	0.0549 (7)	0.0347 (5)	0.0548 (7)	−0.0055 (5)	−0.0117 (5)	0.0014 (5)
C3	0.0566 (7)	0.0475 (6)	0.0456 (6)	−0.0065 (5)	−0.0153 (5)	0.0041 (5)
C4	0.0543 (7)	0.0467 (6)	0.0374 (5)	−0.0092 (5)	−0.0113 (5)	−0.0068 (4)
C5	0.0517 (7)	0.0342 (5)	0.0396 (5)	−0.0050 (4)	−0.0113 (5)	−0.0071 (4)
C6	0.0440 (6)	0.0332 (5)	0.0374 (5)	−0.0066 (4)	−0.0085 (4)	−0.0057 (4)
C7	0.0595 (7)	0.0365 (5)	0.0418 (6)	−0.0074 (5)	−0.0172 (5)	−0.0058 (4)
C8	0.0688 (8)	0.0402 (6)	0.0402 (6)	−0.0060 (5)	−0.0158 (5)	−0.0082 (4)
C9	0.0570 (7)	0.0386 (5)	0.0439 (6)	−0.0076 (5)	−0.0149 (5)	−0.0072 (4)
C10	0.0441 (6)	0.0451 (6)	0.0376 (5)	−0.0091 (5)	−0.0100 (4)	−0.0048 (4)
C11	0.0509 (7)	0.0473 (6)	0.0404 (6)	−0.0124 (5)	−0.0090 (5)	−0.0070 (4)
C12	0.0499 (7)	0.0577 (7)	0.0500 (7)	−0.0112 (6)	−0.0058 (5)	−0.0204 (6)
C13	0.0604 (9)	0.0892 (11)	0.0426 (7)	−0.0066 (8)	−0.0139 (6)	−0.0193 (7)
C14	0.0716 (10)	0.0849 (11)	0.0427 (7)	0.0005 (8)	−0.0199 (6)	0.0043 (7)
C15	0.0583 (8)	0.0526 (7)	0.0484 (7)	−0.0022 (6)	−0.0151 (6)	0.0014 (5)
C16	0.0901 (12)	0.0352 (6)	0.0849 (11)	−0.0072 (7)	−0.0160 (9)	−0.0185 (7)
C17	0.1071 (14)	0.0604 (9)	0.0567 (8)	−0.0066 (9)	−0.0215 (8)	−0.0245 (7)

O1—C1	1.3585 (13)	C8—H8A	0.9300
O1—C16	1.4140 (15)	C9—C10	1.4689 (15)
O2—C4	1.3725 (13)	C9—H9A	0.9300
O2—C17	1.4114 (18)	C10—C11	1.3911 (16)
O3—C7	1.2186 (14)	C10—C15	1.3941 (16)
O4—N1	1.214 (2)	C11—C12	1.3775 (16)
O5—N1	1.2241 (18)	C11—H11A	0.9300
N1—C12	1.477 (2)	C12—C13	1.375 (2)
C1—C2	1.4006 (17)	C13—C14	1.372 (2)
C1—C6	1.4007 (14)	C13—H13A	0.9300
C2—C3	1.3736 (18)	C14—C15	1.3894 (19)
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.3876 (17)	C15—H15A	0.9300
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.3781 (16)	C16—H16B	0.9600
C5—C6	1.4035 (14)	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.4986 (15)	C17—H17B	0.9600
C7—C8	1.4754 (15)	C17—H17C	0.9600
C8—C9	1.3121 (17)
C1—O1—C16	119.72 (11)	C10—C9—H9A	117.1
C4—O2—C17	117.66 (10)	C11—C10—C15	118.74 (11)
O4—N1—O5	124.18 (17)	C11—C10—C9	121.88 (10)
O4—N1—C12	118.90 (13)	C15—C10—C9	119.38 (11)
O5—N1—C12	116.90 (18)	C12—C11—C10	119.18 (12)
O1—C1—C2	122.18 (10)	C12—C11—H11A	120.4
O1—C1—C6	118.48 (10)	C10—C11—H11A	120.4
C2—C1—C6	119.33 (10)	C13—C12—C11	122.74 (13)
C3—C2—C1	121.03 (11)	C13—C12—N1	119.30 (13)
C3—C2—H2A	119.5	C11—C12—N1	117.96 (13)
C1—C2—H2A	119.5	C14—C13—C12	118.00 (12)
C2—C3—C4	120.09 (11)	C14—C13—H13A	121.0
C2—C3—H3A	120.0	C12—C13—H13A	121.0
C4—C3—H3A	120.0	C13—C14—C15	121.00 (13)
O2—C4—C5	124.45 (11)	C13—C14—H14A	119.5
O2—C4—C3	115.96 (10)	C15—C14—H14A	119.5
C5—C4—C3	119.58 (10)	C14—C15—C10	120.34 (13)
C4—C5—C6	121.45 (10)	C14—C15—H15A	119.8
C4—C5—H5A	119.3	C10—C15—H15A	119.8
C6—C5—H5A	119.3	O1—C16—H16A	109.5
C1—C6—C5	118.51 (10)	O1—C16—H16B	109.5
C1—C6—C7	126.70 (9)	H16A—C16—H16B	109.5
C5—C6—C7	114.78 (9)	O1—C16—H16C	109.5
O3—C7—C8	119.73 (10)	H16A—C16—H16C	109.5
O3—C7—C6	118.73 (10)	H16B—C16—H16C	109.5
C8—C7—C6	121.54 (10)	O2—C17—H17A	109.5
C9—C8—C7	122.75 (11)	O2—C17—H17B	109.5
C9—C8—H8A	118.6	H17A—C17—H17B	109.5
C7—C8—H8A	118.6	O2—C17—H17C	109.5
C8—C9—C10	125.75 (11)	H17A—C17—H17C	109.5
C8—C9—H9A	117.1	H17B—C17—H17C	109.5
C16—O1—C1—C2	−1.1 (2)	C5—C6—C7—C8	−173.92 (12)
C16—O1—C1—C6	178.45 (13)	O3—C7—C8—C9	4.2 (2)
O1—C1—C2—C3	178.92 (12)	C6—C7—C8—C9	−175.88 (13)
C6—C1—C2—C3	−0.6 (2)	C7—C8—C9—C10	−179.56 (12)
C1—C2—C3—C4	1.0 (2)	C8—C9—C10—C11	−12.8 (2)
C17—O2—C4—C5	−6.0 (2)	C8—C9—C10—C15	166.73 (14)
C17—O2—C4—C3	175.36 (15)	C15—C10—C11—C12	0.15 (19)
C2—C3—C4—O2	178.06 (13)	C9—C10—C11—C12	179.72 (12)
C2—C3—C4—C5	−0.6 (2)	C10—C11—C12—C13	−0.3 (2)
O2—C4—C5—C6	−178.65 (12)	C10—C11—C12—N1	179.37 (12)
C3—C4—C5—C6	−0.1 (2)	O4—N1—C12—C13	−168.10 (17)
O1—C1—C6—C5	−179.64 (11)	O5—N1—C12—C13	10.5 (2)
C2—C1—C6—C5	−0.08 (18)	O4—N1—C12—C11	12.2 (2)
O1—C1—C6—C7	−0.96 (19)	O5—N1—C12—C11	−169.16 (15)
C2—C1—C6—C7	178.60 (12)	C11—C12—C13—C14	0.1 (2)
C4—C5—C6—C1	0.41 (19)	N1—C12—C13—C14	−179.54 (15)
C4—C5—C6—C7	−178.42 (12)	C12—C13—C14—C15	0.2 (3)
C1—C6—C7—O3	−172.69 (14)	C13—C14—C15—C10	−0.4 (2)
C5—C6—C7—O3	6.03 (19)	C11—C10—C15—C14	0.2 (2)
C1—C6—C7—C8	7.4 (2)	C9—C10—C15—C14	−179.40 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O2i	0.93	2.55	3.4773 (18)	172.
C8—H8A···O1	0.93	2.12	2.7727 (16)	126.
C17—H17A···O5ii	0.96	2.50	3.309 (2)	142.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O2i	0.93	2.55	3.4773 (18)	172
C8—H8A⋯O1	0.93	2.12	2.7727 (16)	126
C17—H17A⋯O5ii	0.96	2.50	3.309 (2)	142

Symmetry codes: (i) ; (ii) .