(E)-N'-[1-(4-Amino-phen-yl)ethyl-idene]benzohydrazide.

Crystals of the title compound, C(15)H(15)N(3)O, were obtained from a condensation reaction of benzohydrazide and 1-(4-amino-phen-yl)ethanone. The mol-ecule assumes an E configuration with the amino-phenyl and benzohydrazide units located on opposite sites of the C=N double bond. In the crystal structure, the benzene rings of the mol-ecule are slightly twisted with respect to the central hydrazide, the dihedral angles being 18.22 (12) and 27.62 (12)°. The crystal structure contains inter-molecular N-H⋯O and weak C-H⋯N hydrogen bonding.

Related literature

For general background, see: Okabe et al. (1993 ▶); Shan et al. (2003 ▶). For a related structure, see: Shan et al. (2008 ▶).

Experimental

Crystal data

C15H15N3O

M = 253.30

Monoclinic,

a = 12.261 (9) Å

b = 5.324 (4) Å

c = 19.882 (15) Å

β = 94.57 (2)°

V = 1293.7 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 (2) K

0.42 × 0.36 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

10914 measured reflections

2303 independent reflections

1594 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.156

S = 1.05

2303 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019004/xu2432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019004/xu2432Isup2.hkl

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

C15H15N3O	F000 = 536
Mr = 253.30	Dx = 1.301 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3256 reflections
a = 12.261 (9) Å	θ = 2.0–25.0º
b = 5.324 (4) Å	µ = 0.08 mm−1
c = 19.882 (15) Å	T = 295 (2) K
β = 94.57 (2)º	Prism, yellow
V = 1293.7 (17) Å3	0.42 × 0.36 × 0.32 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2303 independent reflections
Radiation source: fine-focus sealed tube	1594 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
Detector resolution: 10.00 pixels mm-1	θmax = 25.2º
T = 295(2) K	θmin = 1.9º
ω scans	h = −14→13
Absorption correction: none	k = −6→6
10914 measured reflections	l = −23→23

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0957P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.156	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.21 e Å−3
2303 reflections	Δρmin = −0.15 e Å−3
174 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (5)
Secondary atom site location: difference Fourier map

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
N1	0.31065 (12)	0.5389 (3)	0.53755 (7)	0.0458 (4)
H1	0.3349	0.3881	0.5344	0.055*
N2	0.21647 (12)	0.6131 (3)	0.49876 (7)	0.0445 (4)
N3	−0.22800 (14)	0.7277 (3)	0.31088 (8)	0.0636 (5)
H3A	−0.2549	0.6375	0.2777	0.076*
H3B	−0.2616	0.8609	0.3223	0.076*
O1	0.33735 (12)	0.9288 (3)	0.58300 (7)	0.0629 (5)
C1	0.45840 (15)	0.6003 (3)	0.62353 (9)	0.0436 (5)
C2	0.51973 (16)	0.3936 (4)	0.60532 (10)	0.0542 (6)
H2	0.5019	0.3119	0.5646	0.065*
C3	0.60765 (18)	0.3099 (4)	0.64827 (12)	0.0653 (6)
H3	0.6489	0.1736	0.6357	0.078*
C4	0.63412 (18)	0.4268 (4)	0.70911 (11)	0.0646 (6)
H4	0.6927	0.3692	0.7375	0.078*
C5	0.57340 (18)	0.6300 (4)	0.72783 (10)	0.0620 (6)
H5	0.5904	0.7084	0.7691	0.074*
C6	0.48743 (16)	0.7162 (4)	0.68502 (9)	0.0545 (6)
H6	0.4479	0.8553	0.6976	0.065*
C7	0.36407 (15)	0.7045 (4)	0.58023 (8)	0.0449 (5)
C8	0.17939 (15)	0.4585 (3)	0.45231 (8)	0.0402 (5)
C9	0.07430 (14)	0.5262 (3)	0.41483 (8)	0.0397 (5)
C10	0.01535 (15)	0.7400 (3)	0.43293 (8)	0.0450 (5)
H10	0.0437	0.8397	0.4685	0.054*
C11	−0.08369 (16)	0.8054 (4)	0.39912 (9)	0.0480 (5)
H11	−0.1199	0.9492	0.4118	0.058*
C12	−0.12988 (15)	0.6578 (4)	0.34612 (9)	0.0477 (5)
C13	−0.07350 (17)	0.4434 (4)	0.32890 (9)	0.0536 (6)
H13	−0.1032	0.3403	0.2944	0.064*
C14	0.02614 (16)	0.3814 (3)	0.36233 (9)	0.0496 (5)
H14	0.0622	0.2378	0.3492	0.060*
C15	0.23698 (17)	0.2176 (3)	0.43604 (10)	0.0544 (6)
H15A	0.3141	0.2481	0.4361	0.082*
H15B	0.2093	0.1587	0.3923	0.082*
H15C	0.2241	0.0929	0.4694	0.082*

	U11	U22	U33	U12	U13	U23
N1	0.0451 (10)	0.0419 (9)	0.0490 (9)	0.0038 (7)	−0.0059 (7)	−0.0028 (7)
N2	0.0436 (10)	0.0446 (10)	0.0437 (8)	0.0004 (7)	−0.0059 (7)	0.0019 (7)
N3	0.0596 (12)	0.0707 (12)	0.0572 (10)	0.0061 (10)	−0.0166 (8)	0.0062 (9)
O1	0.0652 (10)	0.0461 (9)	0.0735 (10)	0.0083 (7)	−0.0176 (8)	−0.0082 (7)
C1	0.0390 (11)	0.0435 (11)	0.0478 (10)	−0.0025 (9)	0.0012 (8)	0.0016 (8)
C2	0.0469 (13)	0.0506 (12)	0.0643 (12)	0.0026 (9)	0.0000 (10)	−0.0059 (10)
C3	0.0582 (14)	0.0520 (13)	0.0851 (16)	0.0127 (11)	0.0029 (12)	0.0019 (11)
C4	0.0526 (14)	0.0656 (15)	0.0735 (15)	0.0092 (11)	−0.0078 (11)	0.0144 (12)
C5	0.0581 (14)	0.0714 (15)	0.0537 (12)	0.0061 (12)	−0.0128 (10)	−0.0033 (11)
C6	0.0530 (13)	0.0545 (13)	0.0545 (12)	0.0089 (10)	−0.0046 (9)	−0.0078 (10)
C7	0.0440 (12)	0.0439 (11)	0.0463 (10)	0.0004 (9)	0.0011 (8)	−0.0029 (8)
C8	0.0467 (11)	0.0343 (10)	0.0395 (9)	−0.0034 (8)	0.0020 (8)	0.0043 (7)
C9	0.0440 (11)	0.0346 (10)	0.0398 (9)	−0.0047 (8)	−0.0011 (8)	0.0047 (7)
C10	0.0487 (12)	0.0419 (11)	0.0433 (10)	−0.0021 (9)	−0.0031 (8)	−0.0043 (8)
C11	0.0474 (12)	0.0476 (12)	0.0487 (10)	0.0028 (9)	0.0030 (9)	0.0027 (9)
C12	0.0485 (12)	0.0492 (12)	0.0442 (10)	−0.0055 (9)	−0.0036 (9)	0.0126 (8)
C13	0.0646 (14)	0.0466 (12)	0.0462 (11)	−0.0057 (10)	−0.0160 (10)	0.0004 (9)
C14	0.0622 (14)	0.0380 (11)	0.0469 (10)	0.0019 (9)	−0.0071 (10)	−0.0020 (8)
C15	0.0584 (13)	0.0437 (12)	0.0588 (12)	0.0055 (10)	−0.0095 (10)	−0.0035 (9)

N1—C7	1.355 (2)	C5—H5	0.9300
N1—N2	1.394 (2)	C6—H6	0.9300
N1—H1	0.8600	C8—C9	1.481 (3)
N2—C8	1.292 (2)	C8—C15	1.512 (3)
N3—C12	1.394 (2)	C9—C14	1.391 (2)
N3—H3A	0.8600	C9—C10	1.410 (3)
N3—H3B	0.8600	C10—C11	1.385 (3)
O1—C7	1.241 (2)	C10—H10	0.9300
C1—C6	1.390 (3)	C11—C12	1.398 (3)
C1—C2	1.396 (3)	C11—H11	0.9300
C1—C7	1.493 (3)	C12—C13	1.391 (3)
C2—C3	1.394 (3)	C13—C14	1.384 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.376 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.381 (3)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.380 (3)
C7—N1—N2	120.00 (16)	N2—C8—C9	116.56 (16)
C7—N1—H1	120.0	N2—C8—C15	123.33 (17)
N2—N1—H1	120.0	C9—C8—C15	120.10 (16)
C8—N2—N1	116.36 (16)	C14—C9—C10	116.33 (17)
C12—N3—H3A	120.0	C14—C9—C8	122.89 (17)
C12—N3—H3B	120.0	C10—C9—C8	120.74 (16)
H3A—N3—H3B	120.0	C11—C10—C9	121.78 (17)
C6—C1—C2	118.19 (18)	C11—C10—H10	119.1
C6—C1—C7	118.33 (17)	C9—C10—H10	119.1
C2—C1—C7	123.48 (17)	C10—C11—C12	120.77 (18)
C3—C2—C1	119.9 (2)	C10—C11—H11	119.6
C3—C2—H2	120.0	C12—C11—H11	119.6
C1—C2—H2	120.0	C13—C12—N3	121.40 (18)
C4—C3—C2	120.7 (2)	C13—C12—C11	117.86 (18)
C4—C3—H3	119.6	N3—C12—C11	120.73 (19)
C2—C3—H3	119.6	C14—C13—C12	120.99 (17)
C3—C4—C5	119.8 (2)	C14—C13—H13	119.5
C3—C4—H4	120.1	C12—C13—H13	119.5
C5—C4—H4	120.1	C13—C14—C9	122.26 (18)
C6—C5—C4	119.8 (2)	C13—C14—H14	118.9
C6—C5—H5	120.1	C9—C14—H14	118.9
C4—C5—H5	120.1	C8—C15—H15A	109.5
C5—C6—C1	121.62 (19)	C8—C15—H15B	109.5
C5—C6—H6	119.2	H15A—C15—H15B	109.5
C1—C6—H6	119.2	C8—C15—H15C	109.5
O1—C7—N1	122.51 (17)	H15A—C15—H15C	109.5
O1—C7—C1	121.83 (16)	H15B—C15—H15C	109.5
N1—C7—C1	115.66 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1i	0.86	2.44	3.169 (3)	143
C15—H15C···N2ii	0.96	2.62	3.468 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1i	0.86	2.44	3.169 (3)	143
C15—H15C⋯N2ii	0.96	2.62	3.468 (3)	147

Symmetry codes: (i) ; (ii) .