(Z)-2-(4-Nitro­benzyl­idene)-1-benzofuran-3(2H)-one

Reddy, J.S.; Ravikumar, N.; Prasad, J.V.; Krishna, G.G.; Solomon, K.A.

doi:10.1107/S1600536811041869

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2961

doi:10.1107/S1600536811041869

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(Z)-2-(4-Nitrobenzylidene)-1-benzofuran-3(2H)-one

J. Satyanarayana Reddy,^a N. Ravikumar,^a J. Venkata Prasad,^a G. Gopi Krishna ^a and K. Anand Solomon ^a ^*

^aSankar Foundation Research Institute, Naiduthota, Vepagunta, Visakhapatnam, Andhra pradesh 530 047, India
^*Correspondence e-mail: anand.dcb@gmail.com

(Received 15 September 2011; accepted 11 October 2011; online 12 October 2011)

In the crystal structure of the title compound, C₁₅H₉NO₄, weak C—H⋯O interactions generate rings with R²₂(8) motifs. The supramolecular aggregation is completed by the presence of C—H⋯O and van der Waals interactions.

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_r = 267.23
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.03
2116 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) -x+1, -y, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811041869/zj2025sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811041869/zj2025Isup3.cml

checkCIF report

Comment top

Aurones belong flavonoids family, which are structurally isomers of flavones. They form essential structural scaffolds in many natural and synthetic molecules possessing diverse therapeutic properties (Villemin et al. 1998) Several multifunctionalized aurones were reported to exhibit anti-malarial (Souard et al. 2010) and anti-histamine (Wang et al. 2007) properties.

The title compound (Fig.1),C₁₅H₉NO₄,crystallized in triclinic space group P-1 with two molecules in the assymetric unit (Fig.2).The crystal structure of (I) is stabilized by C—H···O interactions.The range of H···O distances (Table 1) found in (I) agrees with those found for C—H···O hydrogen bonds (Desiraju & Steiner,1999). The coumaranone moiety at C10 is in co-planar conformation [C7—C8—C9—C10=179.55 (13)°].The translational related molecules interact with each other via weak C—H···O [C9—H9···O2: H9···O2 = 2.50 Å, θ = 143°] hydrogen bonds along the c axis, and form a one dimensional chain (Fig. 3).

Related literature top

For the synthesis and biological activity of substituted aurones, see: Varma et al. (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 top

3-coumaranone was allowed to react with 4-nitrobenzaldehyde in ethanolic solution of potassium hydroxide for 30 minutes to yield the title compound (Fig.4). The pure product was obtained by recrystallization in methanol.

Computing details top

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 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of (Z)-2-(4-nitrobenzylidene)benzofuran-3(2H)-one. (Thermal ellipsoids are at 50% probability level).
	Fig. 2. Crystal packing diagram of the title compound.
	Fig. 3. The synthetic scheme of the title compound.

(Z)-2-(4-Nitrobenzylidene)-1-benzofuran-3(2H)-one top

Crystal data top

C₁₅H₉NO₄	Z = 2
M_r = 267.23	F(000) = 276
Triclinic, P1	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	1869 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
T_min = 0.932, T_max = 0.955	k = −8→8
12519 measured reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0599P)² + 0.1178P] where P = (F_o² + 2F_c²)/3
2116 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₉NO₄	γ = 102.043 (1)°
M_r = 267.23	V = 605.09 (3) Å³
Triclinic, P1	Z = 2
a = 6.6916 (2) Å	Mo Kα radiation
b = 7.4708 (2) Å	µ = 0.11 mm⁻¹
c = 12.6414 (3) Å	T = 303 K
α = 100.459 (1)°	0.30 × 0.20 × 0.20 mm
β = 93.019 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2116 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1869 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.955	R_int = 0.020
12519 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
2116 reflections	Δρ_min = −0.25 e Å⁻³
181 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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₉NO₄
M_r	267.23
Crystal system, space group	Triclinic, P1
Temperature (K)	303
a, b, c (Å)	6.6916 (2), 7.4708 (2), 12.6414 (3)
α, β, γ (°)	100.459 (1), 93.019 (2), 102.043 (1)
V (Å³)	605.09 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.932, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	12519, 2116, 1869
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.03
No. of reflections	2116
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z.

Acknowledgements

The authors thank the Managing Trustee and the Founder Trustee of the Sankar Foundation for their financial support and encouragement. We also acknowledge, The Head, SAIF, IIT-Chennai, for the data collection.

References

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