(E)-2-(4-Nitro­benzyl­ideneamino)benzamide

Wang, S.-L.; Yang, K.; Wang, X.-S.; Tu, S.-J.

doi:10.1107/S160053680902203X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1581

doi:10.1107/S160053680902203X

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(E)-2-(4-Nitrobenzylideneamino)benzamide

Shu-Liang Wang,^a ^* Ke Yang,^a Xiang-Shan Wang ^a and Shu-Jiang Tu ^a

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou Jiangsu 221116, People's Republic of China
^*Correspondence e-mail: slwangxznu@yahoo.cn

(Received 4 June 2009; accepted 10 June 2009; online 13 June 2009)

The title compound, C₁₄H₁₁N₃O₃, adopts an E conformation, with a dihedral angle of 41.8 (1) ° between the mean planes of the two benzene rings. One of the amino H atoms forms an intramolecular hydrogen bond with the amide N atom, while the other H atom forms an intermolecular hydrogen bond with the carbonyl O atom of an adjacent molecule, forming dimers about inversion centers. A non-classical intermolecular C—H⋯O hydrogen bond also links adjacent molecules into dimers.

Related literature

For Schiff bases complexes with metal ions, see: Kannan & Ramesh (2006 ); Lv et al. (2006 ); Maurya et al. (2006 ); Parekh et al. (2006 ); Vanco et al. (2004 ).

Experimental

Crystal data

C₁₄H₁₁N₃O₃
M_r = 269.26
Monoclinic, P 2₁ /c
a = 7.3863 (2) Å
b = 12.2657 (3) Å
c = 14.1414 (4) Å
β = 97.248 (1)°
V = 1270.95 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.45 × 0.29 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
9505 measured reflections
2278 independent reflections
1809 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.04
2278 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O2ⁱ	0.93	2.44	3.1903 (19)	138
N1—H1B⋯O3ⁱⁱ	0.904 (18)	2.059 (19)	2.9581 (17)	173.3 (15)
N1—H1A⋯N2	0.877 (18)	1.999 (18)	2.7027 (18)	136.4 (15)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902203X/pv2166sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902203X/pv2166Isup2.hkl

checkCIF report

Comment top

Schiff bases are well known as ligands for many metal ions, such as copper(II) (Vanco et al., 2005), Vanadium(IV, V) (Maurya et al., 2006) and ruthenium(III) (Kannan & Ramesh, 2006). Some of metal Schiff base complexes possess biological activities. For example, it was reported that oxovanadium(IV) complexes with Schiff bases had antifungal activity (Parekh et al., 2006), cobalt(II) and copper(II) complexes of valine-derived Schiff bases possessed antimicrobial activity (Lv et al., 2006). We have synthesized the title compound, (I), by the reaction of 4-nitrobenzaldehyde, 2-aminobenzamide in an ionic liquid at room temperature which is reported in this article.

The X-ray crystal structure determination indicates that the title compound adopts an E-configuration (Fig. 1). The plane defined as the atoms of C7, C8, C9, N2 and H8A is nearly parallel to the benzene ring (C9—C14), forming a dihedral angle of 0.8 (1)°. The dihedral angle between the basal plane (atoms C7, C8, C9, N2 and H8A) and the other benzene ring (C2—C7) is 41.1 (1)°. the benzene rings make a dihedral angle of 41.8 (1)°.

The classical (N—H···O) and unclassical (C—H···O) hydrogen bonds are present in the crystal structure of (I) (Table 1). One of the hydrogen atoms (H1A) on the amino group forms an intra-molecular hydrogen bond (N1—H1A···N2) with the atom N2, while the other hydrogen atom (H1B) forms an inter-molecular hydrogen bond of the type N—H···O with the atom O3 in the adjacent molecule, forming dimmers. An unclassical intermolecular hydrogen bond (C13—H13A···O2) also links the adjacent molecules into dimmers (Fig. 2). The above inter-molecular hydrogen bonds link the molecules into polymers.

Related literature top

For Schiff bases complexes with metal ions, see: Kannan & Ramesh (2006); Lv et al. (2006); Maurya et al. (2006); Parekh et al. (2006); Vanco et al. (2004).

Experimental top

The title compound, (I), was prepared by the reaction of 4-nitrobenzaldehyde (2 mmol, 0.302 g) and 2-aminobenzamide (2 mmol, 0.272 g) in an ionic liquid of [Bmim]Br (Bmim = 1-butyl-3-methylimidazolium) (2 ml) at 353 K; m.p. 457–458 K. The single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing diagram showing the hydrogen-bonding network in the crystal for (I).

(E)-2-(4-Nitrobenzylideneamino)benzamide top

Crystal data top

C₁₄H₁₁N₃O₃	F(000) = 560
M_r = 269.26	D_x = 1.407 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 457–458 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.3863 (2) Å	Cell parameters from 3148 reflections
b = 12.2657 (3) Å	θ = 2.2–25.8°
c = 14.1414 (4) Å	µ = 0.10 mm⁻¹
β = 97.248 (1)°	T = 296 K
V = 1270.95 (6) Å³	Block, yellow
Z = 4	0.45 × 0.29 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1809 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 25.2°, θ_min = 2.2°
ϕ and ω scans	h = −8→8
9505 measured reflections	k = −14→14
2278 independent reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0436P)² + 0.1992P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2278 reflections	Δρ_max = 0.14 e Å⁻³
190 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (3)

Crystal data top

C₁₄H₁₁N₃O₃	V = 1270.95 (6) Å³
M_r = 269.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3863 (2) Å	µ = 0.10 mm⁻¹
b = 12.2657 (3) Å	T = 296 K
c = 14.1414 (4) Å	0.45 × 0.29 × 0.16 mm
β = 97.248 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1809 reflections with I > 2σ(I)
9505 measured reflections	R_int = 0.026
2278 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.14 e Å⁻³
2278 reflections	Δρ_min = −0.14 e Å⁻³
190 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
N2	0.29424 (15)	0.81888 (9)	0.04882 (9)	0.0480 (3)
O2	0.66701 (16)	0.86265 (9)	0.54680 (8)	0.0669 (3)
O3	−0.03944 (14)	0.58880 (8)	−0.10923 (7)	0.0556 (3)
C9	0.39628 (18)	0.86357 (11)	0.21085 (11)	0.0459 (4)
C2	0.10787 (17)	0.76078 (11)	−0.09651 (10)	0.0413 (3)
C1	0.06905 (17)	0.64827 (11)	−0.06033 (10)	0.0412 (3)
N3	0.66097 (17)	0.79210 (10)	0.48528 (10)	0.0525 (3)
C12	0.56915 (18)	0.81749 (11)	0.38992 (10)	0.0445 (4)
C7	0.20752 (18)	0.84286 (11)	−0.04369 (11)	0.0445 (3)
N1	0.15232 (19)	0.61634 (11)	0.02351 (10)	0.0536 (4)
C8	0.30111 (19)	0.88799 (12)	0.11590 (11)	0.0503 (4)
H8A	0.2447	0.9554	0.1046	0.060*
C14	0.3976 (2)	0.93889 (11)	0.28377 (11)	0.0521 (4)
H14A	0.3381	1.0053	0.2721	0.063*
C13	0.4860 (2)	0.91691 (11)	0.37357 (11)	0.0518 (4)
H13A	0.4892	0.9684	0.4220	0.062*
C3	0.0323 (2)	0.78476 (12)	−0.18910 (11)	0.0497 (4)
H3A	−0.0348	0.7314	−0.2248	0.060*
C11	0.5690 (2)	0.74035 (12)	0.31915 (13)	0.0540 (4)
H11A	0.6261	0.6734	0.3318	0.065*
C10	0.4840 (2)	0.76367 (12)	0.23011 (12)	0.0552 (4)
H10A	0.4844	0.7124	0.1817	0.066*
O1	0.72849 (17)	0.70200 (9)	0.49945 (9)	0.0717 (4)
C4	0.0538 (2)	0.88540 (14)	−0.22967 (12)	0.0592 (4)
H4A	0.0017	0.8994	−0.2918	0.071*
C5	0.1527 (2)	0.96491 (14)	−0.17769 (13)	0.0645 (5)
H5A	0.1680	1.0329	−0.2047	0.077*
C6	0.2289 (2)	0.94391 (12)	−0.08568 (13)	0.0590 (4)
H6A	0.2957	0.9981	−0.0510	0.071*
H1A	0.226 (2)	0.6618 (14)	0.0573 (13)	0.067 (5)*
H1B	0.121 (2)	0.5508 (15)	0.0458 (11)	0.060 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0529 (7)	0.0391 (6)	0.0509 (8)	−0.0056 (5)	0.0025 (6)	−0.0035 (6)
O2	0.0898 (8)	0.0617 (7)	0.0489 (7)	−0.0009 (6)	0.0074 (6)	−0.0088 (6)
O3	0.0673 (6)	0.0468 (6)	0.0495 (7)	−0.0128 (5)	−0.0050 (5)	−0.0018 (5)
C9	0.0473 (7)	0.0400 (7)	0.0507 (9)	−0.0063 (6)	0.0079 (6)	−0.0063 (7)
C2	0.0418 (7)	0.0405 (7)	0.0421 (8)	0.0023 (5)	0.0079 (6)	0.0007 (6)
C1	0.0440 (7)	0.0399 (7)	0.0404 (8)	−0.0003 (6)	0.0076 (6)	−0.0039 (6)
N3	0.0589 (7)	0.0471 (7)	0.0530 (9)	−0.0034 (6)	0.0135 (6)	−0.0007 (7)
C12	0.0464 (7)	0.0428 (8)	0.0452 (9)	−0.0052 (6)	0.0091 (6)	−0.0023 (7)
C7	0.0477 (7)	0.0388 (7)	0.0472 (9)	0.0022 (6)	0.0066 (6)	0.0012 (6)
N1	0.0678 (8)	0.0412 (7)	0.0484 (8)	−0.0137 (6)	−0.0058 (7)	0.0056 (6)
C8	0.0544 (8)	0.0396 (7)	0.0568 (10)	−0.0013 (6)	0.0067 (7)	−0.0037 (7)
C14	0.0666 (9)	0.0358 (7)	0.0544 (10)	0.0019 (6)	0.0098 (8)	−0.0051 (7)
C13	0.0696 (9)	0.0390 (8)	0.0482 (10)	−0.0030 (7)	0.0130 (8)	−0.0091 (7)
C3	0.0507 (8)	0.0529 (8)	0.0456 (9)	0.0022 (6)	0.0066 (7)	0.0024 (7)
C11	0.0569 (8)	0.0431 (8)	0.0610 (10)	0.0080 (6)	0.0041 (7)	−0.0095 (7)
C10	0.0620 (9)	0.0466 (8)	0.0553 (11)	0.0055 (7)	0.0014 (8)	−0.0167 (7)
O1	0.0907 (8)	0.0550 (7)	0.0685 (8)	0.0134 (6)	0.0062 (7)	0.0070 (6)
C4	0.0638 (9)	0.0637 (10)	0.0506 (10)	0.0091 (8)	0.0089 (8)	0.0151 (8)
C5	0.0774 (11)	0.0480 (9)	0.0693 (12)	0.0043 (8)	0.0140 (9)	0.0188 (9)
C6	0.0702 (10)	0.0384 (8)	0.0683 (12)	−0.0041 (7)	0.0080 (8)	0.0019 (8)

Geometric parameters (Å, º) top

N2—C8	1.2684 (19)	N1—H1A	0.877 (18)
N2—C7	1.4131 (19)	N1—H1B	0.904 (18)
O2—N3	1.2238 (16)	C8—H8A	0.9300
O3—C1	1.2299 (15)	C14—C13	1.379 (2)
C9—C14	1.384 (2)	C14—H14A	0.9300
C9—C10	1.397 (2)	C13—H13A	0.9300
C9—C8	1.466 (2)	C3—C4	1.379 (2)
C2—C3	1.389 (2)	C3—H3A	0.9300
C2—C7	1.4053 (19)	C11—C10	1.365 (2)
C2—C1	1.5118 (19)	C11—H11A	0.9300
C1—N1	1.3241 (19)	C10—H10A	0.9300
N3—O1	1.2186 (16)	C4—C5	1.375 (2)
N3—C12	1.4645 (19)	C4—H4A	0.9300
C12—C13	1.372 (2)	C5—C6	1.375 (2)
C12—C11	1.377 (2)	C5—H5A	0.9300
C7—C6	1.392 (2)	C6—H6A	0.9300

C8—N2—C7	121.60 (12)	C13—C14—C9	120.91 (14)
C14—C9—C10	118.75 (14)	C13—C14—H14A	119.5
C14—C9—C8	120.25 (13)	C9—C14—H14A	119.5
C10—C9—C8	120.99 (13)	C12—C13—C14	118.60 (13)
C3—C2—C7	118.09 (13)	C12—C13—H13A	120.7
C3—C2—C1	116.21 (12)	C14—C13—H13A	120.7
C7—C2—C1	125.67 (13)	C4—C3—C2	121.88 (14)
O3—C1—N1	121.61 (13)	C4—C3—H3A	119.1
O3—C1—C2	119.27 (12)	C2—C3—H3A	119.1
N1—C1—C2	119.12 (12)	C10—C11—C12	118.97 (14)
O1—N3—O2	123.15 (14)	C10—C11—H11A	120.5
O1—N3—C12	118.47 (13)	C12—C11—H11A	120.5
O2—N3—C12	118.38 (12)	C11—C10—C9	120.79 (14)
C13—C12—C11	121.95 (14)	C11—C10—H10A	119.6
C13—C12—N3	119.32 (13)	C9—C10—H10A	119.6
C11—C12—N3	118.73 (13)	C5—C4—C3	119.60 (15)
C6—C7—C2	119.41 (14)	C5—C4—H4A	120.2
C6—C7—N2	121.19 (13)	C3—C4—H4A	120.2
C2—C7—N2	119.27 (12)	C4—C5—C6	119.97 (15)
C1—N1—H1A	119.1 (12)	C4—C5—H5A	120.0
C1—N1—H1B	117.8 (10)	C6—C5—H5A	120.0
H1A—N1—H1B	122.9 (15)	C5—C6—C7	121.04 (15)
N2—C8—C9	121.19 (13)	C5—C6—H6A	119.5
N2—C8—H8A	119.4	C7—C6—H6A	119.5
C9—C8—H8A	119.4

C3—C2—C1—O3	−7.15 (18)	C10—C9—C14—C13	1.0 (2)
C7—C2—C1—O3	170.60 (13)	C8—C9—C14—C13	179.76 (13)
C3—C2—C1—N1	173.09 (13)	C11—C12—C13—C14	1.0 (2)
C7—C2—C1—N1	−9.2 (2)	N3—C12—C13—C14	−178.97 (12)
O1—N3—C12—C13	177.42 (13)	C9—C14—C13—C12	−1.6 (2)
O2—N3—C12—C13	−2.95 (19)	C7—C2—C3—C4	0.5 (2)
O1—N3—C12—C11	−2.57 (19)	C1—C2—C3—C4	178.39 (13)
O2—N3—C12—C11	177.05 (13)	C13—C12—C11—C10	0.1 (2)
C3—C2—C7—C6	−0.8 (2)	N3—C12—C11—C10	−179.88 (13)
C1—C2—C7—C6	−178.46 (13)	C12—C11—C10—C9	−0.7 (2)
C3—C2—C7—N2	−176.60 (12)	C14—C9—C10—C11	0.2 (2)
C1—C2—C7—N2	5.7 (2)	C8—C9—C10—C11	−178.58 (14)
C8—N2—C7—C6	41.8 (2)	C2—C3—C4—C5	0.0 (2)
C8—N2—C7—C2	−142.45 (14)	C3—C4—C5—C6	−0.2 (2)
C7—N2—C8—C9	−178.08 (12)	C4—C5—C6—C7	−0.1 (3)
C14—C9—C8—N2	−178.12 (14)	C2—C7—C6—C5	0.6 (2)
C10—C9—C8—N2	0.6 (2)	N2—C7—C6—C5	176.34 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O2ⁱ	0.93	2.44	3.1903 (19)	138
N1—H1B···O3ⁱⁱ	0.904 (18)	2.059 (19)	2.9581 (17)	173.3 (15)
N1—H1A···N2	0.877 (18)	1.999 (18)	2.7027 (18)	136.4 (15)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₃
M_r	269.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.3863 (2), 12.2657 (3), 14.1414 (4)
β (°)	97.248 (1)
V (Å³)	1270.95 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.29 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9505, 2278, 1809
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.04
No. of reflections	2278
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O2ⁱ	0.93	2.44	3.1903 (19)	137.9
N1—H1B···O3ⁱⁱ	0.904 (18)	2.059 (19)	2.9581 (17)	173.3 (15)
N1—H1A···N2	0.877 (18)	1.999 (18)	2.7027 (18)	136.4 (15)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z.

Acknowledgements

We are grateful to the National Natural Science Foundation of China (20802061), the Natural Science Foundation (08KJD150019) and the Qing Lan Project (08QLT001) of Jiangsu Education Committee for financial support.

References

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