(2E)-N'-[(E)-Benzyl-idene]-3-phenyl-prop-2-enohydrazide from synchrotron radiation.

In the title compound, C(16)H(14)N(2)O, the dihedral angle between the phenyl rings is 25.48 (12)°. An E conformation is found for each of the imine [1.269 (3) Å] and ethyl-ene [1.313 (3) Å] bonds. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, leading to zigzag chains along [010]. Supra-molecular layers in the ab plane are formed, whereby the chains are linked by C-H⋯N and C-H⋯π inter-actions.

Related literature

For the biological activity of (E)-cinnamoylhydrazone derivatives against Chagas’ disease, see: Carvalho et al. (2012b ▶). For background to Chagas’ disease, see: Rassi et al. (2010 ▶); Soeiro & de Castro (2011 ▶). For related structural studies, see: Carvalho et al. (2009 ▶, 2010a ▶,b ▶, 2012a ▶).

Experimental

Crystal data

C16H14N2O

M = 250.30

Orthorhombic,

a = 11.473 (19) Å

b = 7.507 (13) Å

c = 30.50 (5) Å

V = 2627 (8) Å3

Z = 8

Synchrotron radiation

λ = 0.6943 Å

μ = 0.04 mm−1

T = 120 K

0.12 × 0.03 × 0.02 mm

Data collection

Bruker SMART APEXII CCD diffractometer

14542 measured reflections

1876 independent reflections

1442 reflections with I > 2σ(I)

R int = 0.084

θmax = 22.7°

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.140

S = 1.05

1876 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028504/hb6861sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028504/hb6861Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028504/hb6861Isup3.cml

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

C16H14N2O	F(000) = 1056
Mr = 250.30	Dx = 1.266 Mg m−3
Orthorhombic, Pbca	Synchrotron radiation, λ = 0.6943 Å
Hall symbol: -P 2ybc	Cell parameters from 996 reflections
a = 11.473 (19) Å	θ = 3.2–25.1°
b = 7.507 (13) Å	µ = 0.04 mm−1
c = 30.50 (5) Å	T = 120 K
V = 2627 (8) Å3	Needle, colourless
Z = 8	0.12 × 0.03 × 0.02 mm

Bruker SMART APEXII CCD diffractometer	1442 reflections with I > 2σ(I)
Radiation source: Daresbury SRS station 9.8	Rint = 0.084
Silicon 111 monochromator	θmax = 22.7°, θmin = 2.6°
fine–slice ω scans	h = −12→12
14542 measured reflections	k = −8→8
1876 independent reflections	l = −33→33

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0776P)2 + 0.9415P] where P = (Fo2 + 2Fc2)/3
1876 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.38302 (13)	0.0885 (2)	0.60236 (5)	0.0381 (5)
N1	0.23795 (16)	0.2057 (3)	0.66603 (6)	0.0349 (5)
N2	0.25029 (17)	0.2886 (3)	0.62606 (6)	0.0371 (5)
H2N	0.209 (2)	0.385 (2)	0.6201 (8)	0.045*
C1	0.14001 (19)	0.2034 (3)	0.73493 (7)	0.0338 (6)
C2	0.21991 (19)	0.0947 (3)	0.75586 (7)	0.0373 (6)
H2	0.2886	0.0588	0.7409	0.045*
C3	0.2010 (2)	0.0384 (3)	0.79800 (7)	0.0403 (6)
H3	0.2554	−0.0392	0.8117	0.048*
C4	0.1040 (2)	0.0931 (3)	0.82057 (8)	0.0413 (7)
H4	0.0924	0.0559	0.8500	0.050*
C5	0.0236 (2)	0.2021 (4)	0.80048 (8)	0.0412 (7)
H5	−0.0442	0.2389	0.8159	0.049*
C6	0.0418 (2)	0.2580 (3)	0.75771 (8)	0.0386 (6)
H6	−0.0134	0.3341	0.7439	0.046*
C7	0.15938 (19)	0.2706 (3)	0.69056 (7)	0.0353 (6)
H7	0.1121	0.3649	0.6799	0.042*
C8	0.3245 (2)	0.2246 (3)	0.59613 (7)	0.0357 (6)
C9	0.32566 (19)	0.3248 (3)	0.55473 (7)	0.0344 (6)
H9	0.2785	0.4282	0.5518	0.041*
C10	0.3909 (2)	0.2735 (3)	0.52168 (7)	0.0374 (6)
H10	0.4399	0.1736	0.5268	0.045*
C11	0.39690 (19)	0.3527 (3)	0.47781 (7)	0.0366 (6)
C12	0.3407 (2)	0.5093 (4)	0.46697 (8)	0.0447 (7)
H12	0.2972	0.5710	0.4887	0.054*
C13	0.3468 (2)	0.5770 (4)	0.42517 (9)	0.0501 (7)
H13	0.3079	0.6851	0.4181	0.060*
C14	0.4090 (2)	0.4885 (4)	0.39369 (8)	0.0505 (7)
H14	0.4134	0.5354	0.3648	0.061*
C15	0.4645 (2)	0.3332 (4)	0.40364 (8)	0.0498 (7)
H15	0.5069	0.2716	0.3816	0.060*
C16	0.4593 (2)	0.2651 (4)	0.44565 (8)	0.0437 (7)
H16	0.4988	0.1574	0.4525	0.052*

	U11	U22	U33	U12	U13	U23
O1	0.0345 (9)	0.0435 (10)	0.0362 (9)	0.0027 (8)	0.0002 (7)	0.0019 (8)
N1	0.0314 (10)	0.0474 (13)	0.0258 (10)	−0.0017 (9)	−0.0002 (8)	0.0017 (9)
N2	0.0373 (11)	0.0464 (14)	0.0276 (10)	0.0004 (9)	0.0001 (9)	0.0051 (9)
C1	0.0332 (12)	0.0437 (14)	0.0246 (12)	−0.0079 (11)	−0.0008 (10)	−0.0013 (10)
C2	0.0323 (13)	0.0443 (14)	0.0353 (13)	0.0027 (11)	0.0020 (10)	−0.0037 (11)
C3	0.0409 (14)	0.0453 (16)	0.0345 (13)	0.0002 (12)	−0.0052 (11)	0.0027 (11)
C4	0.0493 (16)	0.0497 (16)	0.0249 (12)	−0.0115 (13)	−0.0027 (11)	0.0007 (11)
C5	0.0339 (13)	0.0536 (17)	0.0362 (14)	−0.0068 (12)	0.0071 (11)	−0.0074 (12)
C6	0.0351 (13)	0.0428 (14)	0.0379 (14)	−0.0004 (11)	−0.0053 (11)	−0.0002 (11)
C7	0.0324 (13)	0.0423 (15)	0.0311 (13)	−0.0003 (11)	−0.0039 (10)	−0.0005 (10)
C8	0.0314 (12)	0.0457 (16)	0.0301 (13)	−0.0062 (12)	−0.0013 (10)	−0.0023 (11)
C9	0.0322 (12)	0.0411 (14)	0.0297 (12)	0.0003 (10)	−0.0021 (10)	0.0020 (10)
C10	0.0353 (13)	0.0439 (15)	0.0330 (13)	−0.0003 (11)	−0.0017 (11)	0.0015 (11)
C11	0.0315 (12)	0.0504 (16)	0.0279 (12)	−0.0045 (12)	−0.0002 (10)	0.0028 (11)
C12	0.0419 (14)	0.0579 (17)	0.0344 (14)	0.0029 (13)	0.0071 (11)	0.0013 (13)
C13	0.0423 (15)	0.0629 (19)	0.0449 (16)	0.0034 (13)	−0.0023 (12)	0.0127 (14)
C14	0.0398 (14)	0.081 (2)	0.0312 (14)	−0.0062 (14)	−0.0015 (11)	0.0134 (14)
C15	0.0394 (14)	0.077 (2)	0.0332 (14)	0.0000 (14)	0.0081 (11)	−0.0064 (14)
C16	0.0389 (14)	0.0530 (16)	0.0391 (15)	0.0035 (12)	0.0008 (11)	0.0019 (12)

O1—C8	1.238 (3)	C7—H7	0.9500
N1—C7	1.269 (3)	C8—C9	1.470 (4)
N1—N2	1.376 (3)	C9—C10	1.313 (3)
N2—C8	1.338 (3)	C9—H9	0.9500
N2—H2N	0.886 (10)	C10—C11	1.466 (4)
C1—C2	1.383 (3)	C10—H10	0.9500
C1—C6	1.386 (4)	C11—C12	1.381 (4)
C1—C7	1.461 (4)	C11—C16	1.381 (4)
C2—C3	1.370 (4)	C12—C13	1.374 (4)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.371 (4)	C13—C14	1.368 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.377 (4)	C14—C15	1.363 (4)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.386 (4)	C15—C16	1.381 (4)
C5—H5	0.9500	C15—H15	0.9500
C6—H6	0.9500	C16—H16	0.9500
C7—N1—N2	115.0 (2)	O1—C8—C9	123.4 (2)
C8—N2—N1	120.5 (2)	N2—C8—C9	114.1 (2)
C8—N2—H2N	119.7 (17)	C10—C9—C8	120.9 (2)
N1—N2—H2N	119.8 (17)	C10—C9—H9	119.5
C2—C1—C6	118.8 (2)	C8—C9—H9	119.5
C2—C1—C7	122.0 (2)	C9—C10—C11	127.5 (3)
C6—C1—C7	119.1 (2)	C9—C10—H10	116.3
C3—C2—C1	120.6 (2)	C11—C10—H10	116.3
C3—C2—H2	119.7	C12—C11—C16	118.5 (2)
C1—C2—H2	119.7	C12—C11—C10	122.8 (2)
C2—C3—C4	120.5 (2)	C16—C11—C10	118.7 (3)
C2—C3—H3	119.8	C13—C12—C11	120.9 (2)
C4—C3—H3	119.8	C13—C12—H12	119.6
C3—C4—C5	119.9 (2)	C11—C12—H12	119.6
C3—C4—H4	120.1	C14—C13—C12	119.8 (3)
C5—C4—H4	120.1	C14—C13—H13	120.1
C4—C5—C6	119.8 (2)	C12—C13—H13	120.1
C4—C5—H5	120.1	C15—C14—C13	120.2 (3)
C6—C5—H5	120.1	C15—C14—H14	119.9
C1—C6—C5	120.3 (2)	C13—C14—H14	119.9
C1—C6—H6	119.8	C14—C15—C16	120.2 (3)
C5—C6—H6	119.8	C14—C15—H15	119.9
N1—C7—C1	121.5 (2)	C16—C15—H15	119.9
N1—C7—H7	119.3	C15—C16—C11	120.3 (3)
C1—C7—H7	119.3	C15—C16—H16	119.8
O1—C8—N2	122.5 (2)	C11—C16—H16	119.8
C7—N1—N2—C8	−175.3 (2)	O1—C8—C9—C10	−0.3 (4)
C6—C1—C2—C3	1.6 (4)	N2—C8—C9—C10	−177.4 (2)
C7—C1—C2—C3	178.0 (2)	C8—C9—C10—C11	176.4 (2)
C1—C2—C3—C4	−1.9 (4)	C9—C10—C11—C12	7.2 (4)
C2—C3—C4—C5	1.6 (4)	C9—C10—C11—C16	−171.3 (2)
C3—C4—C5—C6	−0.9 (4)	C16—C11—C12—C13	−0.2 (4)
C2—C1—C6—C5	−0.9 (3)	C10—C11—C12—C13	−178.7 (2)
C7—C1—C6—C5	−177.4 (2)	C11—C12—C13—C14	0.2 (4)
C4—C5—C6—C1	0.6 (4)	C12—C13—C14—C15	0.2 (4)
N2—N1—C7—C1	−176.63 (19)	C13—C14—C15—C16	−0.6 (4)
C2—C1—C7—N1	14.0 (3)	C14—C15—C16—C11	0.6 (4)
C6—C1—C7—N1	−169.6 (2)	C12—C11—C16—C15	−0.2 (4)
N1—N2—C8—O1	1.4 (3)	C10—C11—C16—C15	178.4 (2)
N1—N2—C8—C9	178.50 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1i	0.88 (2)	1.93 (2)	2.816 (6)	175 (2)
C5—H5···N1ii	0.95	2.57	3.433 (7)	151
C3—H3···Cg1iii	0.95	2.92	3.618 (7)	131
C6—H6···Cg1iv	0.95	2.75	3.645 (7)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O1i	0.88 (2)	1.93 (2)	2.816 (6)	175 (2)
C5—H5⋯N1ii	0.95	2.57	3.433 (7)	151
C3—H3⋯Cg1iii	0.95	2.92	3.618 (7)	131
C6—H6⋯Cg1iv	0.95	2.75	3.645 (7)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .