(Z)-2-(4-Nitro-benzyl-idene)-1-benzofuran-3(2H)-one.

In the crystal structure of the title compound, C(15)H(9)NO(4), weak C-H⋯O inter-actions generate rings with R(2) (2)(8) motifs. The supra-molecular aggregation is completed by the presence of C-H⋯O and van der Waals inter-actions.

Related literature

For the synthesis and biological activity of substituted aurones, see: Varma & Varma (1992 ▶); Beney et al. (2001 ▶); Sim et al. (2008 ▶). For the assignment of conformations and the orientation of the substituents, see: Nardelli (1983 ▶, 1995 ▶); Klyne & Prelog (1960 ▶). For hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For the diverse theraputic properties of aurones, see: Villemin et al. (1998 ▶). Several multifunctionalized aurones have been reported to exhibit anti-malarial (Souard et al. 2010 ▶) and anti-histamine (Wang et al. 2007 ▶) properties.

Experimental

Crystal data

C15H9NO4

M = 267.23

Triclinic,

a = 6.6916 (2) Å

b = 7.4708 (2) Å

c = 12.6414 (3) Å

α = 100.459 (1)°

β = 93.019 (2)°

γ = 102.043 (1)°

V = 605.09 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 303 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004) ▶ T min = 0.932, T max = 0.955

12519 measured reflections

2116 independent reflections

1869 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.03

2116 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041869/zj2025sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041869/zj2025Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041869/zj2025Isup3.cml

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

C15H9NO4	Z = 2
Mr = 267.23	F(000) = 276
Triclinic, P1	Dx = 1.467 Mg m−3
Hall symbol: -P 1	Melting point: 460 K
a = 6.6916 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4708 (2) Å	Cell parameters from 7266 reflections
c = 12.6414 (3) Å	θ = 2.8–30.5°
α = 100.459 (1)°	µ = 0.11 mm−1
β = 93.019 (2)°	T = 303 K
γ = 102.043 (1)°	Block, yellow
V = 605.09 (3) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω and φ scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
Tmin = 0.932, Tmax = 0.955	k = −8→8
12519 measured reflections	l = −15→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) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0599P)2 + 0.1178P] where P = (Fo2 + 2Fc2)/3
2116 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.8384 (2)	0.28398 (18)	−0.19093 (11)	0.0456 (3)
C2	0.7837 (2)	0.3025 (2)	−0.29555 (11)	0.0548 (4)
H2	0.6469	0.2729	−0.3234	0.066*
C3	0.9366 (3)	0.3652 (2)	−0.35600 (12)	0.0595 (4)
H3	0.9037	0.3790	−0.4260	0.071*
C4	1.1407 (3)	0.4087 (2)	−0.31413 (12)	0.0586 (4)
H4	1.2417	0.4519	−0.3569	0.070*
C5	1.1987 (2)	0.3898 (2)	−0.21071 (12)	0.0526 (4)
H5	1.3355	0.4179	−0.1830	0.063*
C6	1.0423 (2)	0.32720 (17)	−0.15171 (10)	0.0431 (3)
C7	0.88073 (19)	0.22680 (18)	−0.01762 (11)	0.0429 (3)
C8	0.7214 (2)	0.21929 (19)	−0.10621 (12)	0.0485 (3)
C9	0.8470 (2)	0.17046 (18)	0.07516 (11)	0.0452 (3)
H9	0.7102	0.1217	0.0832	0.054*
C10	0.9913 (2)	0.17343 (17)	0.16591 (10)	0.0411 (3)
C11	0.9136 (2)	0.11596 (19)	0.25736 (11)	0.0470 (3)
H11	0.7727	0.0733	0.2574	0.056*
C12	1.0401 (2)	0.12085 (19)	0.34749 (11)	0.0477 (3)
H12	0.9866	0.0829	0.4083	0.057*
C13	1.2473 (2)	0.18320 (18)	0.34544 (10)	0.0444 (3)
C14	1.3322 (2)	0.23746 (19)	0.25581 (11)	0.0475 (3)
H14	1.4736	0.2769	0.2562	0.057*
C15	1.2041 (2)	0.23210 (18)	0.16603 (11)	0.0452 (3)
H15	1.2592	0.2677	0.1050	0.054*
N1	1.3855 (2)	0.19263 (19)	0.44088 (10)	0.0575 (3)
O1	1.07162 (13)	0.29789 (13)	−0.04757 (7)	0.0459 (3)
O2	0.53638 (16)	0.16865 (18)	−0.10414 (10)	0.0732 (4)
O3	1.5647 (2)	0.2687 (3)	0.44252 (12)	0.1051 (6)
O4	1.31586 (19)	0.12304 (19)	0.51458 (9)	0.0760 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0521 (8)	0.0404 (7)	0.0431 (7)	0.0118 (6)	−0.0073 (6)	0.0070 (5)
C2	0.0648 (9)	0.0512 (8)	0.0466 (8)	0.0140 (7)	−0.0133 (7)	0.0092 (6)
C3	0.0845 (11)	0.0537 (8)	0.0392 (7)	0.0150 (8)	−0.0068 (7)	0.0108 (6)
C4	0.0747 (10)	0.0542 (8)	0.0465 (8)	0.0093 (7)	0.0062 (7)	0.0142 (6)
C5	0.0543 (8)	0.0539 (8)	0.0483 (8)	0.0072 (6)	0.0001 (6)	0.0135 (6)
C6	0.0513 (8)	0.0395 (7)	0.0382 (7)	0.0108 (5)	−0.0043 (5)	0.0084 (5)
C7	0.0404 (7)	0.0435 (7)	0.0439 (7)	0.0085 (5)	−0.0025 (5)	0.0090 (5)
C8	0.0443 (8)	0.0499 (8)	0.0513 (8)	0.0110 (6)	−0.0058 (6)	0.0121 (6)
C9	0.0406 (7)	0.0476 (7)	0.0468 (8)	0.0085 (5)	0.0004 (6)	0.0102 (6)
C10	0.0443 (7)	0.0385 (6)	0.0405 (7)	0.0092 (5)	0.0016 (5)	0.0084 (5)
C11	0.0424 (7)	0.0525 (8)	0.0481 (8)	0.0108 (6)	0.0064 (6)	0.0143 (6)
C12	0.0537 (8)	0.0522 (8)	0.0414 (7)	0.0143 (6)	0.0092 (6)	0.0159 (6)
C13	0.0511 (8)	0.0451 (7)	0.0378 (7)	0.0124 (6)	−0.0011 (6)	0.0098 (5)
C14	0.0418 (7)	0.0547 (8)	0.0450 (8)	0.0055 (6)	−0.0003 (6)	0.0145 (6)
C15	0.0463 (7)	0.0510 (7)	0.0385 (7)	0.0067 (6)	0.0023 (5)	0.0145 (6)
N1	0.0585 (8)	0.0713 (8)	0.0436 (7)	0.0123 (6)	−0.0027 (6)	0.0187 (6)
O1	0.0426 (5)	0.0546 (5)	0.0400 (5)	0.0067 (4)	−0.0041 (4)	0.0154 (4)
O2	0.0437 (6)	0.1012 (9)	0.0775 (8)	0.0093 (6)	−0.0083 (5)	0.0363 (7)
O3	0.0651 (8)	0.1611 (15)	0.0821 (9)	−0.0170 (9)	−0.0255 (7)	0.0637 (10)
O4	0.0768 (8)	0.1133 (10)	0.0450 (6)	0.0215 (7)	0.0047 (5)	0.0342 (6)

C1—C6	1.3780 (19)	C9—C10	1.4541 (18)
C1—C2	1.3922 (19)	C9—H9	0.9300
C1—C8	1.453 (2)	C10—C11	1.3935 (19)
C2—C3	1.365 (2)	C10—C15	1.3993 (19)
C2—H2	0.9300	C11—C12	1.3736 (19)
C3—C4	1.388 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.371 (2)
C4—C5	1.384 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.3816 (19)
C5—C6	1.369 (2)	C13—N1	1.4628 (18)
C5—H5	0.9300	C14—C15	1.3752 (19)
C6—O1	1.3837 (16)	C14—H14	0.9300
C7—C9	1.331 (2)	C15—H15	0.9300
C7—O1	1.3777 (16)	N1—O3	1.2127 (17)
C7—C8	1.4900 (18)	N1—O4	1.2150 (17)
C8—O2	1.2200 (17)
C6—C1—C2	119.87 (14)	C7—C9—H9	115.1
C6—C1—C8	106.79 (12)	C10—C9—H9	115.1
C2—C1—C8	133.31 (13)	C11—C10—C15	118.52 (12)
C3—C2—C1	118.13 (14)	C11—C10—C9	118.28 (12)
C3—C2—H2	120.9	C15—C10—C9	123.20 (12)
C1—C2—H2	120.9	C12—C11—C10	121.54 (13)
C2—C3—C4	120.73 (14)	C12—C11—H11	119.2
C2—C3—H3	119.6	C10—C11—H11	119.2
C4—C3—H3	119.6	C13—C12—C11	118.23 (13)
C5—C4—C3	122.12 (15)	C13—C12—H12	120.9
C5—C4—H4	118.9	C11—C12—H12	120.9
C3—C4—H4	118.9	C12—C13—C14	122.37 (13)
C6—C5—C4	115.94 (14)	C12—C13—N1	119.42 (12)
C6—C5—H5	122.0	C14—C13—N1	118.21 (13)
C4—C5—H5	122.0	C15—C14—C13	118.91 (13)
C5—C6—C1	123.20 (13)	C15—C14—H14	120.5
C5—C6—O1	123.91 (12)	C13—C14—H14	120.5
C1—C6—O1	112.89 (12)	C14—C15—C10	120.40 (13)
C9—C7—O1	124.72 (12)	C14—C15—H15	119.8
C9—C7—C8	126.03 (13)	C10—C15—H15	119.8
O1—C7—C8	109.24 (11)	O3—N1—O4	122.99 (13)
O2—C8—C1	130.02 (13)	O3—N1—C13	118.44 (13)
O2—C8—C7	125.87 (14)	O4—N1—C13	118.57 (13)
C1—C8—C7	104.10 (11)	C7—O1—C6	106.90 (10)
C7—C9—C10	129.88 (13)
C6—C1—C2—C3	−0.5 (2)	C7—C9—C10—C11	176.04 (13)
C8—C1—C2—C3	−178.41 (14)	C7—C9—C10—C15	−3.6 (2)
C1—C2—C3—C4	0.2 (2)	C15—C10—C11—C12	1.8 (2)
C2—C3—C4—C5	0.4 (2)	C9—C10—C11—C12	−177.82 (12)
C3—C4—C5—C6	−0.6 (2)	C10—C11—C12—C13	−0.4 (2)
C4—C5—C6—C1	0.2 (2)	C11—C12—C13—C14	−1.2 (2)
C4—C5—C6—O1	179.20 (12)	C11—C12—C13—N1	179.06 (12)
C2—C1—C6—C5	0.3 (2)	C12—C13—C14—C15	1.2 (2)
C8—C1—C6—C5	178.73 (12)	N1—C13—C14—C15	−179.02 (12)
C2—C1—C6—O1	−178.73 (11)	C13—C14—C15—C10	0.3 (2)
C8—C1—C6—O1	−0.35 (15)	C11—C10—C15—C14	−1.8 (2)
C6—C1—C8—O2	178.90 (15)	C9—C10—C15—C14	177.86 (12)
C2—C1—C8—O2	−3.0 (3)	C12—C13—N1—O3	−171.28 (15)
C6—C1—C8—C7	−1.28 (14)	C14—C13—N1—O3	9.0 (2)
C2—C1—C8—C7	176.79 (14)	C12—C13—N1—O4	9.1 (2)
C9—C7—C8—O2	3.7 (2)	C14—C13—N1—O4	−170.61 (13)
O1—C7—C8—O2	−177.66 (13)	C9—C7—O1—C6	175.88 (12)
C9—C7—C8—C1	−176.09 (13)	C8—C7—O1—C6	−2.75 (13)
O1—C7—C8—C1	2.52 (14)	C5—C6—O1—C7	−177.09 (12)
O1—C7—C9—C10	2.1 (2)	C1—C6—O1—C7	1.98 (14)
C8—C7—C9—C10	−179.55 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1	0.93	2.32	2.9547 (16)	125
C9—H9···O2i	0.93	2.50	3.2951 (14)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1	0.93	2.32	2.9547 (16)	125
C9—H9⋯O2i	0.93	2.50	3.2951 (14)	143

Symmetry code: (i) .