N'-[1-(2-Amino-phen-yl)ethyl-idene]benzo-hydrazide.

The title compound, C(15)H(15)N(3)O, was obtained by a condensation reaction between o-amino-acetophenone and benzoyl hydrazine. The mol-ecule displays an E configuration about the C=N bond. Intra-molecular N-H⋯N hydrogen bonds are formed between the 2-amino-phenyl and imine groups. In the crystal, dimers are formed between mol-ecules linked by inter-molecular N-H⋯O hydrogen bonds from the 2-amino-phenyl group. In addition there are inter-molecular N-H⋯O hydrogen bonds between the amine and carbonyl groups of adjacent mol-ecules. The mol-ecule is twisted rather than planar due to a steric inter-action 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 = 253.30

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 0.98

2894 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010937/bv2135Isup2.hkl

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

C15H15N3O	F(000) = 536
Mr = 253.30	Dx = 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

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

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(Fo2) + (0.0722P)2] where P = (Fo2 + 2Fc2)/3
2894 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .