N′-[1-(2-Amino­phen­yl)ethyl­idene]benzo­hydrazide

Singh, V.P.; Singh, S.

doi:10.1107/S1600536810010937

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1172

https://doi.org/10.1107/S1600536810010937

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N′-[1-(2-Aminophenyl)ethylidene]benzohydrazide

Vinod P. Singh ^a ^* and Shweta Singh ^a

^aFaculty of Science, Department of Chemistry, Banaras Hindu University, Varanasi, U. P. 221 005, India
^*Correspondence e-mail: singvp@yahoo.co.in

(Received 6 November 2009; accepted 23 March 2010; online 24 April 2010)

The title compound, C₁₅H₁₅N₃O, was obtained by a condensation reaction between o-aminoacetophenone and benzoyl hydrazine. The molecule displays an E configuration about the C=N bond. Intramolecular N—H⋯N hydrogen bonds are formed between the 2-aminophenyl and imine groups. In the crystal, dimers are formed between molecules linked by intermolecular N—H⋯O hydrogen bonds from the 2-aminophenyl group. In addition there are intermolecular N—H⋯O hydrogen bonds between the amine and carbonyl groups of adjacent molecules. The molecule is twisted rather than planar due to a steric interaction between the central amide group and the two outer benzene rings. The dihedral angles between this central group and the two rings are 23.29 (9) and 24.96 (9)°.

Related literature

For the biological properties of hydrazones derived from the condensation reactions of hydrazides with aldehydes or ketones, see: Gupta et al. (2007 ); Kocyigit-Kaymakcioglu et al. (2009 ); Kou et al. (2009 ); Mahalingam et al. (2009 ); Sundaraval et al. (2009 ); Yin et al. (2007 ); Zhang et al. (2007 ). For related structures, see: Fun et al. (2008a ,b ); Qiu & Zhao (2008 ); Qiu (2009 ); Ren (2009 ); Xiao & Wei (2009 ).

Experimental

Crystal data

C₁₅H₁₅N₃O
M_r = 253.30
Monoclinic, P 2₁ /c
a = 13.7531 (10) Å
b = 5.1575 (3) Å
c = 18.7178 (13) Å
β = 105.917 (7)°
V = 1276.78 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.33 × 0.25 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.780, T_max = 1.000
5257 measured reflections
2894 independent reflections
1839 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.125
S = 0.98
2894 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1ⁱ	0.86	2.41	3.1611 (15)	147
N1—H1A⋯O1ⁱⁱ	0.86	2.29	3.0856 (16)	154
N1—H1B⋯N2	0.86	2.03	2.6626 (16)	130
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999 ); software used to prepare material for publication: CIFTAB (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810010937/bv2135sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810010937/bv2135Isup2.hkl

checkCIF report

Comment top

Hydrazones derived from the condensation reactions of hydrazides with aldehydes or ketones show excellent biological properties, such as antimicrobial, antitubercular, anticancer and antimalarial (Kocyigit-Kaymakcioglu et al., 2009; Kou et al., 2009; Mahalingam et al.., 2009; Sundaravel et al., 2009; Yin et al., 2007; Zhang et al.,2007. The hydrazones are also important for their use as plasticizers and stabilizers for polymers, polymerization initiators, antioxidants and as indicators (Gupta et al., 2007). Recently, a large number of hydrazone compounds have been reported (Qiu et al., 2008; Qiu, 2009; Ren et al., 2009). In this paper, a new hydrazone compound, derived from the condensation reaction of 2-aminoacetophenone and benzoyl hydrazine, has been reported.

The molecular structure of the title compound is shown in the fig. 1. The molecule and displays an E configuration about the C=N double bond. All bond lengths are within normal ranges (Xiao et al., 2009; Fun et al., 2008a,b). The molecular conformation is stabilized by an intramolecular N—H···.O hydrogen bond and short contact bonds (Fig. 1). In the crystal there are both inter- and intra-molecular hydrogen bonding involving the amine protons. In-plane dimers (r.m.s. deviation for N1 N2 N3 C10–C16 and equivalent atoms = 0.016 Å) are formed between molecules linked by N—H···O hydrogen bonds from the 2-aminophenyl moiety (Fig. 2). In addition there are intermolecular out of plane N—H···O hydrogen bonds between amine and carbonyl group of adjoining molecules (Fig. 3). Intramolecular N—H···N hydrogen bonds are formed between the 2-aminophenyl and imine moieties within the same molecule. The molecule is twisted rather than planar due to steric interaction between the central amide group and the two end groups. The torsion angles between this central group and the two ends are 23.29 (9) and 24.96 (9)° respectively.

Related literature top

For the biological properties of hydrazones derived from the condensation reactions of hydrazides with aldehydes or ketones, see: Gupta et al. (2007); Kocyigit-Kaymakcioglu et al. (2009); Kou et al. (2009); Mahalingam et al. (2009); Sundaraval et al. (2009); Yin et al. (2007); Zhang et al. (2007). For related structures, see: Fun et al. (2008a,b); Qiu & Zhao (2008); Qiu 2009); Ren (2009); Xiao & Wei (2009).

Experimental top

An ethanolic solution of benzoyl hydazine (50 ml, 6.8 g) was taken in a round bottom flask followed by dropwise addition of ethanolic solution of o-aminoacetophenone (50 ml, 6.05 ml) with stirring. The above solution was refluxed for 4-5 h and gave a yellow transparent solution. On keeping the solution in open air for 5-6 h in a beaker, yellow crystals of the product were obtained.

Structure description top

For the biological properties of hydrazones derived from the condensation reactions of hydrazides with aldehydes or ketones, see: Gupta et al. (2007); Kocyigit-Kaymakcioglu et al. (2009); Kou et al. (2009); Mahalingam et al. (2009); Sundaraval et al. (2009); Yin et al. (2007); Zhang et al. (2007). For related structures, see: Fun et al. (2008a,b); Qiu & Zhao (2008); Qiu 2009); Ren (2009); Xiao & Wei (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: CIFTAB (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular diagram with labeled atoms of Benzoic acid [1-(2-amino-phenyl)- ethylidene]-hydrazide. Hydrogen bonds are shown by dashed lines.
	Fig. 2. Diagram showing the formation of in-plane intermolecular hydrogen-bonded dimers. Hydrogen bonds are shown by dashed lines.
	Fig. 3. Packing diagram showing both in-plane and out of plane intermolecular hydrogen bonding. Hydrogen bonds are shown by dashed lines.

N'-[1-(2-Aminophenyl)ethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₅N₃O	F(000) = 536
M_r = 253.30	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 449 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.7531 (10) Å	Cell parameters from 2381 reflections
b = 5.1575 (3) Å	θ = 2.1–28.9°
c = 18.7178 (13) Å	µ = 0.09 mm⁻¹
β = 105.917 (7)°	T = 293 K
V = 1276.78 (15) Å³	Block, yellow
Z = 4	0.33 × 0.25 × 0.13 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2894 independent reflections
Radiation source: fine-focus sealed tube	1839 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 16.0938 pixels mm^-1	θ_max = 28.9°, θ_min = 2.3°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = 0→6
T_min = 0.780, T_max = 1.000	l = 0→25
5257 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0722P)²] where P = (F_o² + 2F_c²)/3
2894 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₅N₃O	V = 1276.78 (15) Å³
M_r = 253.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7531 (10) Å	µ = 0.09 mm⁻¹
b = 5.1575 (3) Å	T = 293 K
c = 18.7178 (13) Å	0.33 × 0.25 × 0.13 mm
β = 105.917 (7)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2894 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1839 reflections with I > 2σ(I)
T_min = 0.780, T_max = 1.000	R_int = 0.016
5257 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 0.98	Δρ_max = 0.23 e Å⁻³
2894 reflections	Δρ_min = −0.17 e Å⁻³
173 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.66011 (8)	0.1102 (2)	0.65390 (6)	0.0519 (3)
N1	0.39154 (10)	0.1668 (2)	0.49800 (7)	0.0503 (4)
H1A	0.3786	0.0452	0.4653	0.060*
H1B	0.4518	0.1849	0.5267	0.060*
N2	0.50765 (9)	0.4528 (2)	0.60680 (7)	0.0421 (3)
N3	0.60065 (8)	0.5188 (2)	0.65630 (6)	0.0412 (3)
H3B	0.6115	0.6736	0.6738	0.049*
C1	0.76802 (10)	0.4196 (2)	0.73150 (8)	0.0358 (3)
C2	0.85408 (11)	0.2716 (3)	0.73861 (8)	0.0447 (4)
H2A	0.8526	0.1323	0.7068	0.054*
C3	0.94215 (11)	0.3296 (3)	0.79275 (9)	0.0525 (4)
H3A	0.9999	0.2306	0.7966	0.063*
C4	0.94508 (12)	0.5322 (3)	0.84082 (9)	0.0511 (4)
H4A	1.0042	0.5680	0.8777	0.061*
C5	0.86097 (12)	0.6814 (3)	0.83443 (9)	0.0515 (4)
H5A	0.8632	0.8193	0.8668	0.062*
C6	0.77205 (11)	0.6280 (3)	0.77967 (8)	0.0440 (4)
H6A	0.7153	0.7313	0.7752	0.053*
C7	0.67244 (10)	0.3368 (3)	0.67595 (8)	0.0369 (3)
C9	0.43928 (12)	0.8049 (3)	0.66631 (9)	0.0550 (4)
H9A	0.4936	0.7669	0.7097	0.083*
H9B	0.3770	0.8173	0.6799	0.083*
H9C	0.4525	0.9664	0.6453	0.083*
C10	0.43119 (10)	0.5926 (3)	0.61032 (7)	0.0367 (3)
C11	0.33225 (10)	0.5346 (2)	0.55733 (7)	0.0357 (3)
C12	0.31699 (11)	0.3301 (3)	0.50418 (8)	0.0391 (3)
C13	0.21932 (12)	0.2954 (3)	0.45633 (9)	0.0508 (4)
H13A	0.2085	0.1638	0.4210	0.061*
C14	0.13992 (13)	0.4485 (3)	0.45999 (10)	0.0571 (5)
H14A	0.0762	0.4184	0.4279	0.069*
C15	0.15369 (12)	0.6478 (3)	0.51108 (9)	0.0526 (4)
H15A	0.0997	0.7528	0.5135	0.063*
C16	0.24806 (11)	0.6886 (3)	0.55826 (9)	0.0468 (4)
H16A	0.2568	0.8237	0.5923	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0476 (6)	0.0412 (6)	0.0576 (7)	0.0001 (5)	−0.0013 (5)	−0.0141 (5)
N1	0.0502 (8)	0.0459 (7)	0.0476 (8)	−0.0006 (6)	0.0015 (6)	−0.0132 (6)
N2	0.0344 (6)	0.0422 (7)	0.0416 (7)	−0.0020 (5)	−0.0033 (5)	−0.0061 (5)
N3	0.0364 (7)	0.0354 (6)	0.0431 (7)	−0.0027 (5)	−0.0035 (5)	−0.0068 (5)
C1	0.0367 (7)	0.0334 (7)	0.0342 (7)	−0.0036 (6)	0.0044 (6)	0.0011 (6)
C2	0.0416 (8)	0.0453 (8)	0.0434 (9)	0.0002 (7)	0.0052 (6)	−0.0068 (7)
C3	0.0375 (8)	0.0583 (10)	0.0549 (10)	0.0018 (7)	0.0012 (7)	−0.0017 (8)
C4	0.0436 (9)	0.0545 (10)	0.0455 (9)	−0.0107 (8)	−0.0040 (7)	−0.0004 (8)
C5	0.0579 (10)	0.0447 (9)	0.0448 (9)	−0.0076 (7)	0.0023 (7)	−0.0101 (7)
C6	0.0438 (8)	0.0378 (8)	0.0462 (9)	0.0002 (6)	0.0052 (7)	−0.0044 (7)
C7	0.0365 (7)	0.0360 (8)	0.0361 (8)	−0.0017 (6)	0.0063 (6)	−0.0031 (6)
C9	0.0441 (9)	0.0630 (10)	0.0519 (10)	0.0027 (8)	0.0029 (7)	−0.0175 (8)
C10	0.0389 (8)	0.0352 (7)	0.0337 (7)	−0.0045 (6)	0.0064 (6)	0.0020 (6)
C11	0.0351 (7)	0.0345 (7)	0.0337 (7)	−0.0034 (6)	0.0028 (6)	0.0034 (6)
C12	0.0421 (8)	0.0357 (7)	0.0359 (8)	−0.0038 (6)	0.0043 (6)	0.0043 (6)
C13	0.0519 (9)	0.0489 (9)	0.0424 (9)	−0.0075 (8)	−0.0026 (7)	−0.0052 (7)
C14	0.0427 (9)	0.0637 (10)	0.0527 (10)	−0.0068 (8)	−0.0075 (7)	0.0038 (8)
C15	0.0400 (9)	0.0576 (10)	0.0544 (10)	0.0056 (7)	0.0029 (7)	0.0036 (8)
C16	0.0441 (9)	0.0453 (9)	0.0468 (9)	0.0016 (7)	0.0051 (7)	−0.0028 (7)

Geometric parameters (Å, º) top

O1—C7	1.2359 (16)	C5—H5A	0.9300
N1—C12	1.3561 (17)	C6—H6A	0.9300
N1—H1A	0.8600	C9—C10	1.498 (2)
N1—H1B	0.8600	C9—H9A	0.9600
N2—C10	1.2915 (18)	C9—H9B	0.9600
N2—N3	1.4002 (14)	C9—H9C	0.9600
N3—C7	1.3387 (17)	C10—C11	1.4781 (18)
N3—H3B	0.8600	C11—C16	1.4079 (19)
C1—C2	1.3838 (19)	C11—C12	1.4254 (19)
C1—C6	1.3942 (19)	C12—C13	1.4068 (19)
C1—C7	1.4972 (18)	C13—C14	1.364 (2)
C2—C3	1.382 (2)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.381 (2)
C3—C4	1.372 (2)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.371 (2)
C4—C5	1.367 (2)	C15—H15A	0.9300
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.391 (2)

C12—N1—H1A	120.0	C10—C9—H9A	109.5
C12—N1—H1B	120.0	C10—C9—H9B	109.5
H1A—N1—H1B	120.0	H9A—C9—H9B	109.5
C10—N2—N3	116.06 (11)	C10—C9—H9C	109.5
C7—N3—N2	118.84 (11)	H9A—C9—H9C	109.5
C7—N3—H3B	120.6	H9B—C9—H9C	109.5
N2—N3—H3B	120.6	N2—C10—C11	117.74 (12)
C2—C1—C6	118.80 (13)	N2—C10—C9	122.56 (13)
C2—C1—C7	118.32 (12)	C11—C10—C9	119.69 (13)
C6—C1—C7	122.72 (13)	C16—C11—C12	117.51 (12)
C3—C2—C1	120.37 (14)	C16—C11—C10	119.11 (13)
C3—C2—H2A	119.8	C12—C11—C10	123.39 (13)
C1—C2—H2A	119.8	N1—C12—C13	118.61 (13)
C4—C3—C2	120.52 (15)	N1—C12—C11	123.31 (12)
C4—C3—H3A	119.7	C13—C12—C11	118.07 (13)
C2—C3—H3A	119.7	C14—C13—C12	122.14 (15)
C5—C4—C3	119.95 (14)	C14—C13—H13A	118.9
C5—C4—H4A	120.0	C12—C13—H13A	118.9
C3—C4—H4A	120.0	C13—C14—C15	120.38 (15)
C4—C5—C6	120.33 (15)	C13—C14—H14A	119.8
C4—C5—H5A	119.8	C15—C14—H14A	119.8
C6—C5—H5A	119.8	C16—C15—C14	119.08 (15)
C5—C6—C1	120.02 (14)	C16—C15—H15A	120.5
C5—C6—H6A	120.0	C14—C15—H15A	120.5
C1—C6—H6A	120.0	C15—C16—C11	122.81 (14)
O1—C7—N3	123.24 (12)	C15—C16—H16A	118.6
O1—C7—C1	121.04 (12)	C11—C16—H16A	118.6
N3—C7—C1	115.59 (12)

C10—N2—N3—C7	155.32 (13)	N3—N2—C10—C9	−3.0 (2)
C6—C1—C2—C3	0.2 (2)	N2—C10—C11—C16	−178.10 (13)
C7—C1—C2—C3	−175.37 (14)	C9—C10—C11—C16	2.9 (2)
C1—C2—C3—C4	0.9 (2)	N2—C10—C11—C12	1.4 (2)
C2—C3—C4—C5	−1.3 (3)	C9—C10—C11—C12	−177.57 (13)
C3—C4—C5—C6	0.4 (3)	C16—C11—C12—N1	−179.41 (13)
C4—C5—C6—C1	0.7 (2)	C10—C11—C12—N1	1.1 (2)
C2—C1—C6—C5	−1.0 (2)	C16—C11—C12—C13	0.0 (2)
C7—C1—C6—C5	174.34 (14)	C10—C11—C12—C13	−179.53 (13)
N2—N3—C7—O1	−1.7 (2)	N1—C12—C13—C14	178.76 (15)
N2—N3—C7—C1	−177.50 (12)	C11—C12—C13—C14	−0.7 (2)
C2—C1—C7—O1	22.1 (2)	C12—C13—C14—C15	0.9 (3)
C6—C1—C7—O1	−153.29 (15)	C13—C14—C15—C16	−0.3 (3)
C2—C1—C7—N3	−162.04 (13)	C14—C15—C16—C11	−0.4 (2)
C6—C1—C7—N3	22.6 (2)	C12—C11—C16—C15	0.5 (2)
N3—N2—C10—C11	178.06 (11)	C10—C11—C16—C15	−179.94 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.86	2.41	3.1611 (15)	147
N1—H1A···O1ⁱⁱ	0.86	2.29	3.0856 (16)	154
N1—H1B···N2	0.86	2.03	2.6626 (16)	130

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃O
M_r	253.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.7531 (10), 5.1575 (3), 18.7178 (13)
β (°)	105.917 (7)
V (Å³)	1276.78 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.25 × 0.13

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.780, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5257, 2894, 1839
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.680

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.125, 0.98
No. of reflections	2894
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1999), CIFTAB (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1ⁱ	0.86	2.41	3.1611 (15)	146.7
N1—H1A···O1ⁱⁱ	0.86	2.29	3.0856 (16)	153.5
N1—H1B···N2	0.86	2.03	2.6626 (16)	129.9

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

Acknowledgements

The authors thank the CSIR for financial support.

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