N'-[(2E)-3-Phenyl-prop-2-eno-yl]benzo-hydrazide.

In the title compound, C(16)H(14)N(2)O(2), the conformation about the C=C bond is E, and the two amide groups are effectively orthogonal [the C-N-N-C torsion angle is 104.5 (2)°]. In the crystal structure, the amide groups groups associate via N-H⋯O hydrogen bonding, forming supra-molecular tapes with undulating topology along the c-axis direction.

Related literature

For the biological activity of trans-cinnamic acid derivatives, see: Bezerra et al. (2006 ▶); Chung & Shin (2007 ▶); Naz et al. (2006 ▶); Rastogi et al. (1998 ▶); Reddy et al. (1995 ▶). For recent studies directed towards developing drugs for the treatment of tuberculosis, see: Carvalho et al. (2008 ▶).

Experimental

Crystal data

C16H14N2O2

M = 266.29

Monoclinic,

a = 15.9696 (7) Å

b = 10.4563 (5) Å

c = 8.3162 (2) Å

β = 102.072 (3)°

V = 1357.95 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 120 K

0.48 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.636, T max = 0.746

17862 measured reflections

3110 independent reflections

2010 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.172

S = 1.10

3110 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.42 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536809048156/hg2591sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048156/hg2591Isup2.hkl

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

C16H14N2O2	F(000) = 560
Mr = 266.29	Dx = 1.303 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6527 reflections
a = 15.9696 (7) Å	θ = 2.9–27.5°
b = 10.4563 (5) Å	µ = 0.09 mm−1
c = 8.3162 (2) Å	T = 120 K
β = 102.072 (3)°	Block, light-red
V = 1357.95 (9) Å3	0.48 × 0.20 × 0.08 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	3110 independent reflections
Radiation source: Enraf–Nonius FR591 rotating anode	2010 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.086
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→13
Tmin = 0.636, Tmax = 0.746	l = −9→10
17862 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0894P)2] where P = (Fo2 + 2Fc2)/3
3110 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.42 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	0.20786 (9)	0.62832 (14)	0.42536 (16)	0.0272 (4)
O2	0.36866 (9)	0.61547 (14)	0.11169 (15)	0.0249 (4)
N1	0.25365 (10)	0.74825 (18)	0.2337 (2)	0.0239 (4)
HN1	0.2442 (14)	0.779 (2)	0.132 (3)	0.029*
N2	0.33940 (11)	0.73943 (18)	0.3148 (2)	0.0248 (4)
HN2	0.3532 (14)	0.774 (2)	0.410 (3)	0.030*
C1	−0.04530 (13)	0.6129 (2)	0.1175 (2)	0.0233 (5)
C2	−0.07212 (14)	0.6812 (2)	−0.0287 (3)	0.0305 (5)
H2	−0.0322	0.7330	−0.0692	0.037*
C3	−0.15601 (14)	0.6745 (2)	−0.1150 (3)	0.0328 (6)
H3	−0.1733	0.7219	−0.2138	0.039*
C4	−0.21495 (13)	0.5991 (2)	−0.0583 (3)	0.0291 (5)
H4	−0.2725	0.5948	−0.1177	0.035*
C5	−0.18951 (14)	0.5302 (2)	0.0851 (3)	0.0301 (5)
H5	−0.2297	0.4782	0.1244	0.036*
C6	−0.10529 (13)	0.5366 (2)	0.1725 (2)	0.0264 (5)
H6	−0.0884	0.4885	0.2709	0.032*
C7	0.04268 (13)	0.6196 (2)	0.2143 (2)	0.0236 (5)
H7	0.0550	0.5693	0.3115	0.028*
C8	0.10735 (12)	0.6886 (2)	0.1809 (2)	0.0236 (5)
H8	0.0983	0.7412	0.0857	0.028*
C9	0.19296 (12)	0.6835 (2)	0.2911 (2)	0.0211 (4)
C10	0.39296 (12)	0.66689 (19)	0.2472 (2)	0.0203 (5)
C11	0.48306 (12)	0.65355 (19)	0.3422 (2)	0.0208 (5)
C12	0.52237 (13)	0.7406 (2)	0.4602 (2)	0.0226 (5)
H12	0.4913	0.8126	0.4859	0.027*
C13	0.60701 (13)	0.7227 (2)	0.5409 (2)	0.0272 (5)
H13	0.6338	0.7826	0.6213	0.033*
C14	0.65253 (14)	0.6170 (2)	0.5038 (2)	0.0280 (5)
H14	0.7105	0.6050	0.5582	0.034*
C15	0.61300 (13)	0.5296 (2)	0.3873 (2)	0.0278 (5)
H15	0.6438	0.4569	0.3631	0.033*
C16	0.52891 (13)	0.5473 (2)	0.3060 (2)	0.0255 (5)
H16	0.5024	0.4873	0.2255	0.031*

	U11	U22	U33	U12	U13	U23
O1	0.0249 (8)	0.0309 (9)	0.0232 (7)	0.0004 (6)	−0.0008 (6)	0.0013 (6)
O2	0.0223 (8)	0.0286 (9)	0.0214 (7)	−0.0042 (6)	−0.0009 (5)	−0.0019 (6)
N1	0.0140 (9)	0.0337 (11)	0.0212 (8)	−0.0004 (8)	−0.0030 (6)	0.0011 (8)
N2	0.0164 (9)	0.0348 (11)	0.0202 (8)	−0.0005 (8)	−0.0033 (6)	−0.0027 (8)
C1	0.0197 (11)	0.0247 (12)	0.0245 (10)	0.0021 (9)	0.0024 (8)	−0.0015 (8)
C2	0.0213 (11)	0.0354 (13)	0.0335 (11)	−0.0057 (10)	0.0026 (9)	0.0068 (10)
C3	0.0247 (12)	0.0371 (14)	0.0323 (12)	−0.0049 (10)	−0.0038 (9)	0.0084 (10)
C4	0.0174 (11)	0.0292 (13)	0.0369 (12)	0.0000 (9)	−0.0029 (9)	−0.0022 (9)
C5	0.0244 (12)	0.0288 (12)	0.0368 (12)	−0.0087 (10)	0.0056 (9)	−0.0024 (10)
C6	0.0249 (11)	0.0270 (12)	0.0264 (10)	−0.0020 (9)	0.0031 (8)	0.0006 (9)
C7	0.0216 (11)	0.0270 (12)	0.0212 (10)	0.0030 (9)	0.0025 (8)	−0.0012 (8)
C8	0.0218 (11)	0.0262 (11)	0.0209 (10)	0.0041 (9)	0.0004 (8)	−0.0011 (8)
C9	0.0183 (10)	0.0222 (11)	0.0213 (10)	0.0015 (9)	0.0005 (7)	−0.0048 (8)
C10	0.0193 (11)	0.0218 (11)	0.0188 (10)	−0.0031 (8)	0.0014 (7)	0.0041 (8)
C11	0.0181 (10)	0.0231 (11)	0.0204 (10)	−0.0020 (8)	0.0019 (7)	0.0043 (8)
C12	0.0189 (10)	0.0268 (12)	0.0218 (9)	−0.0014 (9)	0.0037 (7)	−0.0001 (8)
C13	0.0202 (11)	0.0328 (13)	0.0264 (10)	−0.0028 (9)	−0.0002 (8)	−0.0034 (9)
C14	0.0181 (10)	0.0357 (13)	0.0274 (11)	0.0019 (9)	−0.0017 (8)	0.0010 (9)
C15	0.0249 (12)	0.0277 (12)	0.0298 (11)	0.0069 (9)	0.0034 (8)	0.0038 (9)
C16	0.0253 (12)	0.0252 (12)	0.0242 (10)	−0.0008 (9)	0.0015 (8)	0.0003 (8)

O1—C9	1.235 (2)	C6—H6	0.9500
O2—C10	1.235 (2)	C7—C8	1.336 (3)
N1—C9	1.348 (3)	C7—H7	0.9500
N1—N2	1.397 (2)	C8—C9	1.479 (3)
N1—HN1	0.89 (2)	C8—H8	0.9500
N2—C10	1.351 (3)	C10—C11	1.496 (3)
N2—HN2	0.86 (2)	C11—C12	1.388 (3)
C1—C6	1.395 (3)	C11—C16	1.398 (3)
C1—C2	1.398 (3)	C12—C13	1.390 (3)
C1—C7	1.467 (3)	C12—H12	0.9500
C2—C3	1.383 (3)	C13—C14	1.392 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.384 (3)	C14—C15	1.384 (3)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.379 (3)	C15—C16	1.384 (3)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.390 (3)	C16—H16	0.9500
C5—H5	0.9500
C9—N1—N2	120.03 (17)	C7—C8—C9	120.44 (18)
C9—N1—HN1	121.9 (14)	C7—C8—H8	119.8
N2—N1—HN1	116.0 (14)	C9—C8—H8	119.8
C10—N2—N1	118.56 (16)	O1—C9—N1	122.52 (17)
C10—N2—HN2	124.2 (16)	O1—C9—C8	123.72 (18)
N1—N2—HN2	117.0 (15)	N1—C9—C8	113.74 (17)
C6—C1—C2	118.08 (18)	O2—C10—N2	121.24 (17)
C6—C1—C7	119.48 (18)	O2—C10—C11	121.69 (17)
C2—C1—C7	122.44 (19)	N2—C10—C11	117.06 (16)
C3—C2—C1	120.8 (2)	C12—C11—C16	119.57 (18)
C3—C2—H2	119.6	C12—C11—C10	123.71 (18)
C1—C2—H2	119.6	C16—C11—C10	116.71 (18)
C2—C3—C4	120.41 (19)	C11—C12—C13	120.21 (19)
C2—C3—H3	119.8	C11—C12—H12	119.9
C4—C3—H3	119.8	C13—C12—H12	119.9
C5—C4—C3	119.58 (19)	C12—C13—C14	119.99 (19)
C5—C4—H4	120.2	C12—C13—H13	120.0
C3—C4—H4	120.2	C14—C13—H13	120.0
C4—C5—C6	120.3 (2)	C15—C14—C13	119.76 (19)
C4—C5—H5	119.9	C15—C14—H14	120.1
C6—C5—H5	119.9	C13—C14—H14	120.1
C5—C6—C1	120.80 (19)	C14—C15—C16	120.5 (2)
C5—C6—H6	119.6	C14—C15—H15	119.8
C1—C6—H6	119.6	C16—C15—H15	119.8
C8—C7—C1	127.24 (19)	C15—C16—C11	119.97 (19)
C8—C7—H7	116.4	C15—C16—H16	120.0
C1—C7—H7	116.4	C11—C16—H16	120.0
C9—N1—N2—C10	104.5 (2)	C7—C8—C9—N1	173.98 (19)
C6—C1—C2—C3	0.7 (3)	N1—N2—C10—O2	4.4 (3)
C7—C1—C2—C3	−178.7 (2)	N1—N2—C10—C11	−176.55 (16)
C1—C2—C3—C4	−0.3 (4)	O2—C10—C11—C12	156.22 (19)
C2—C3—C4—C5	−0.1 (3)	N2—C10—C11—C12	−22.8 (3)
C3—C4—C5—C6	0.1 (3)	O2—C10—C11—C16	−23.0 (3)
C4—C5—C6—C1	0.3 (3)	N2—C10—C11—C16	158.00 (18)
C2—C1—C6—C5	−0.7 (3)	C16—C11—C12—C13	0.5 (3)
C7—C1—C6—C5	178.8 (2)	C10—C11—C12—C13	−178.68 (17)
C6—C1—C7—C8	−179.0 (2)	C11—C12—C13—C14	−0.2 (3)
C2—C1—C7—C8	0.4 (3)	C12—C13—C14—C15	−0.5 (3)
C1—C7—C8—C9	−179.37 (19)	C13—C14—C15—C16	0.8 (3)
N2—N1—C9—O1	9.3 (3)	C14—C15—C16—C11	−0.5 (3)
N2—N1—C9—C8	−172.41 (17)	C12—C11—C16—C15	−0.1 (3)
C7—C8—C9—O1	−7.8 (3)	C10—C11—C16—C15	179.11 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O1i	0.89 (2)	1.95 (2)	2.827 (2)	168 (2)
N2—HN2···O2ii	0.86 (2)	2.01 (2)	2.852 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O1i	0.89 (2)	1.95 (2)	2.827 (2)	168 (2)
N2—HN2⋯O2ii	0.86 (2)	2.01 (2)	2.852 (2)	168 (2)

Symmetry codes: (i) ; (ii) .