(2E)-2-[(3E)-4-Phenyl-but-3-en-2-yl-idene]hydrazinecarboxamide.

In the title compound, C(11)H(13)N(3)O, the phenyl ring is disordered over two sites, with occupancy factors in a 0.520 (17):0.480 (17) ratio. The dihedral angle between the ring planes of the major and minor components of the disordered ring is 12.9 (2)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming R(2) (2)(8) ring motifs. C-H⋯O, C-H⋯N and C-H⋯π inter-actions also occur.

Related literature

For background to the biological activity of semicarbazones, see: Beraldo et al. (2002 ▶); Teixeira et al. (2003 ▶); Du et al. (2004 ▶); Kucukguzel et al. (2006 ▶); Beraldo & Gambino (2004 ▶). For related structures, see: Naik & Palenik (1974 ▶); Wang et al. (2004 ▶); Yathirajan et al. (2006 ▶); Sarojini et al. (2007 ▶).

Experimental

Crystal data

C11H13N3O

M = 203.24

Monoclinic,

a = 15.1094 (8) Å

b = 24.4445 (11) Å

c = 7.0368 (4) Å

β = 109.908 (6)°

V = 2443.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 123 K

0.40 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.987, T max = 1.000

12712 measured reflections

3528 independent reflections

2748 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.176

S = 1.05

3528 reflections

168 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105255X/tk5032sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105255X/tk5032Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105255X/tk5032Isup3.cml

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

C11H13N3O	F(000) = 864
Mr = 203.24	Dx = 1.105 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5469 reflections
a = 15.1094 (8) Å	θ = 3.0–30.9°
b = 24.4445 (11) Å	µ = 0.07 mm−1
c = 7.0368 (4) Å	T = 123 K
β = 109.908 (6)°	Prism, colourless
V = 2443.7 (2) Å3	0.40 × 0.30 × 0.18 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3528 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2748 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.5081 pixels mm-1	θmax = 30.9°, θmin = 3.0°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −34→26
Tmin = 0.987, Tmax = 1.000	l = −7→9
12712 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0981P)2 + 0.6768P] where P = (Fo2 + 2Fc2)/3
3528 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
O1	0.36888 (6)	0.23438 (4)	1.62948 (12)	0.0323 (3)
N1	0.34428 (7)	0.30220 (5)	1.17621 (15)	0.0337 (3)
N2	0.31934 (7)	0.27704 (4)	1.32596 (14)	0.0310 (3)
N3	0.47771 (7)	0.26174 (6)	1.49376 (16)	0.0458 (4)
C1B	0.3063 (5)	0.40506 (19)	0.5724 (7)	0.0301 (9)	0.520 (17)
C2B	0.2428 (5)	0.4316 (2)	0.4074 (6)	0.0354 (10)	0.520 (17)
C3B	0.2747 (6)	0.45824 (19)	0.2685 (6)	0.0405 (13)	0.520 (17)
C4B	0.3701 (6)	0.45829 (14)	0.2947 (8)	0.0409 (13)	0.520 (17)
C5B	0.4336 (6)	0.4317 (2)	0.4598 (11)	0.0469 (14)	0.520 (17)
C6B	0.4017 (5)	0.4051 (2)	0.5986 (11)	0.0434 (11)	0.520 (17)
C7	0.25908 (11)	0.37670 (5)	0.71144 (19)	0.0393 (4)
C8	0.31231 (10)	0.35103 (5)	0.87866 (19)	0.0375 (4)
C9	0.27918 (9)	0.32596 (5)	1.03065 (18)	0.0327 (3)
C10	0.17796 (10)	0.32953 (6)	1.0129 (2)	0.0395 (4)
C11	0.38883 (8)	0.25686 (5)	1.49014 (17)	0.0304 (3)
C3A	0.2443 (5)	0.4630 (2)	0.2639 (7)	0.0458 (13)	0.480 (17)
C4A	0.3345 (6)	0.45553 (15)	0.2576 (7)	0.0378 (13)	0.480 (17)
C5A	0.3972 (6)	0.4208 (2)	0.3956 (10)	0.0408 (14)	0.480 (17)
C6A	0.3697 (5)	0.39363 (19)	0.5398 (9)	0.0337 (11)	0.480 (17)
C2A	0.2169 (4)	0.4358 (2)	0.4081 (7)	0.0402 (11)	0.480 (17)
C1A	0.2795 (4)	0.40110 (19)	0.5461 (6)	0.0276 (10)	0.480 (17)
H7A	0.19470	0.37930	0.69980	0.0470*
H3BA	0.23130	0.47640	0.15570	0.0490*	0.520 (17)
H5BA	0.49890	0.43180	0.47770	0.0560*	0.520 (17)
H6BA	0.44510	0.38700	0.71150	0.0520*	0.520 (17)
H10A	0.17330	0.33360	1.14770	0.0590*
H10B	0.14520	0.29610	0.94940	0.0590*
H10C	0.14890	0.36120	0.92980	0.0590*
H4BA	0.39200	0.47650	0.19980	0.0490*	0.520 (17)
H8A	0.37790	0.34890	0.90100	0.0450*
H2B	0.25980	0.27410	1.31570	0.0370*
H3B	0.52440	0.24890	1.59690	0.0550*
H3C	0.48940	0.27780	1.39300	0.0550*
H2BA	0.17760	0.43160	0.38950	0.0420*	0.520 (17)
H2AA	0.15520	0.44090	0.41240	0.0480*	0.480 (17)
H3AA	0.20150	0.48670	0.16960	0.0550*	0.480 (17)
H4AA	0.35330	0.47410	0.15910	0.0450*	0.480 (17)
H5AA	0.45880	0.41570	0.39130	0.0490*	0.480 (17)
H6AA	0.41250	0.36990	0.63410	0.0400*	0.480 (17)

	U11	U22	U33	U12	U13	U23
O1	0.0234 (4)	0.0505 (6)	0.0224 (4)	0.0004 (3)	0.0069 (3)	0.0096 (3)
N1	0.0334 (5)	0.0409 (6)	0.0276 (5)	−0.0035 (4)	0.0113 (4)	0.0100 (4)
N2	0.0239 (4)	0.0438 (6)	0.0243 (5)	−0.0019 (4)	0.0069 (4)	0.0107 (4)
N3	0.0224 (5)	0.0857 (10)	0.0292 (5)	−0.0024 (5)	0.0086 (4)	0.0155 (5)
C1B	0.045 (2)	0.0227 (15)	0.0208 (13)	0.0012 (14)	0.0088 (15)	0.0032 (10)
C2B	0.045 (2)	0.0379 (17)	0.0259 (14)	0.0056 (16)	0.0156 (14)	0.0043 (11)
C3B	0.059 (3)	0.0386 (18)	0.0276 (14)	0.0065 (18)	0.0197 (17)	0.0131 (11)
C4B	0.065 (3)	0.0320 (15)	0.0343 (18)	−0.0086 (16)	0.028 (2)	0.0002 (13)
C5B	0.055 (3)	0.0457 (19)	0.050 (2)	−0.0018 (19)	0.031 (2)	0.0083 (17)
C6B	0.046 (2)	0.0458 (19)	0.041 (2)	0.0010 (18)	0.0182 (19)	0.0113 (17)
C7	0.0638 (9)	0.0303 (6)	0.0298 (6)	0.0083 (6)	0.0238 (6)	0.0061 (5)
C8	0.0488 (7)	0.0349 (6)	0.0335 (6)	0.0037 (5)	0.0202 (6)	0.0097 (5)
C9	0.0389 (6)	0.0323 (6)	0.0279 (5)	0.0005 (5)	0.0126 (5)	0.0065 (4)
C10	0.0397 (7)	0.0478 (8)	0.0320 (6)	0.0081 (5)	0.0135 (5)	0.0127 (5)
C11	0.0240 (5)	0.0424 (7)	0.0238 (5)	−0.0017 (4)	0.0067 (4)	0.0040 (4)
C3A	0.056 (3)	0.044 (2)	0.0397 (18)	0.0139 (18)	0.0194 (18)	0.0134 (14)
C4A	0.055 (3)	0.0314 (17)	0.0291 (15)	−0.0016 (18)	0.017 (2)	0.0062 (12)
C5A	0.045 (3)	0.0402 (19)	0.044 (2)	0.0033 (16)	0.024 (2)	0.0081 (16)
C6A	0.038 (2)	0.0309 (16)	0.0338 (19)	0.0064 (14)	0.0144 (18)	0.0112 (13)
C2A	0.053 (2)	0.0369 (19)	0.0353 (17)	0.0087 (17)	0.0212 (16)	0.0099 (13)
C1A	0.038 (2)	0.0219 (14)	0.0268 (15)	−0.0032 (14)	0.0161 (14)	−0.0043 (12)

O1—C11	1.2472 (15)	C5A—C6A	1.389 (10)
N1—N2	1.3788 (15)	C5B—C6B	1.389 (10)
N1—C9	1.2915 (17)	C7—C8	1.3344 (18)
N2—C11	1.3618 (15)	C8—C9	1.4610 (19)
N3—C11	1.3398 (17)	C9—C10	1.494 (2)
N2—H2B	0.8800	C2A—H2AA	0.9500
N3—H3B	0.8800	C2B—H2BA	0.9500
N3—H3C	0.8800	C3A—H3AA	0.9500
C1A—C7	1.432 (5)	C3B—H3BA	0.9500
C1A—C6A	1.391 (10)	C4A—H4AA	0.9500
C1A—C2A	1.390 (7)	C4B—H4BA	0.9500
C1B—C2B	1.390 (7)	C5A—H5AA	0.9500
C1B—C6B	1.390 (11)	C5B—H5BA	0.9500
C1B—C7	1.556 (6)	C6A—H6AA	0.9500
C2A—C3A	1.389 (8)	C6B—H6BA	0.9500
C2B—C3B	1.390 (9)	C7—H7A	0.9500
C3A—C4A	1.391 (12)	C8—H8A	0.9500
C3B—C4B	1.390 (13)	C10—H10B	0.9800
C4A—C5A	1.391 (9)	C10—H10C	0.9800
C4B—C5B	1.391 (9)	C10—H10A	0.9800
N2—N1—C9	118.31 (11)	C3A—C2A—H2AA	120.00
N1—N2—C11	118.53 (11)	C1A—C2A—H2AA	120.00
N1—N2—H2B	121.00	C3B—C2B—H2BA	120.00
C11—N2—H2B	121.00	C1B—C2B—H2BA	120.00
C11—N3—H3B	120.00	C4A—C3A—H3AA	120.00
H3B—N3—H3C	120.00	C2A—C3A—H3AA	120.00
C11—N3—H3C	120.00	C4B—C3B—H3BA	120.00
C6A—C1A—C7	117.1 (4)	C2B—C3B—H3BA	120.00
C2A—C1A—C7	122.6 (5)	C5A—C4A—H4AA	120.00
C2A—C1A—C6A	119.9 (5)	C3A—C4A—H4AA	120.00
C2B—C1B—C7	113.5 (6)	C5B—C4B—H4BA	120.00
C2B—C1B—C6B	120.0 (6)	C3B—C4B—H4BA	120.00
C6B—C1B—C7	126.4 (5)	C4A—C5A—H5AA	120.00
C1A—C2A—C3A	120.1 (6)	C6A—C5A—H5AA	120.00
C1B—C2B—C3B	120.0 (7)	C4B—C5B—H5BA	120.00
C2A—C3A—C4A	120.0 (5)	C6B—C5B—H5BA	120.00
C2B—C3B—C4B	120.0 (5)	C5A—C6A—H6AA	120.00
C3A—C4A—C5A	120.0 (6)	C1A—C6A—H6AA	120.00
C3B—C4B—C5B	120.0 (6)	C5B—C6B—H6BA	120.00
C4A—C5A—C6A	120.0 (8)	C1B—C6B—H6BA	120.00
C4B—C5B—C6B	120.0 (8)	C1A—C7—H7A	114.00
C1A—C6A—C5A	120.0 (6)	C1B—C7—H7A	126.00
C1B—C6B—C5B	120.0 (6)	C8—C7—H7A	114.00
C1B—C7—C8	119.7 (3)	C9—C8—H8A	117.00
C1A—C7—C8	132.9 (3)	C7—C8—H8A	117.00
C7—C8—C9	126.08 (15)	C9—C10—H10C	110.00
N1—C9—C8	114.27 (13)	C9—C10—H10B	109.00
C8—C9—C10	120.69 (11)	H10B—C10—H10C	109.00
N1—C9—C10	125.04 (12)	H10A—C10—H10B	110.00
N2—C11—N3	117.53 (11)	H10A—C10—H10C	109.00
O1—C11—N3	122.23 (11)	C9—C10—H10A	110.00
O1—C11—N2	120.24 (12)
C9—N1—N2—C11	−173.34 (11)	C2B—C1B—C7—C8	−178.1 (3)
N2—N1—C9—C8	−179.53 (10)	C6B—C1B—C7—C8	2.8 (6)
N2—N1—C9—C10	1.37 (19)	C1B—C2B—C3B—C4B	0.0 (7)
N1—N2—C11—O1	179.22 (11)	C2B—C3B—C4B—C5B	0.0 (7)
N1—N2—C11—N3	−1.40 (17)	C3B—C4B—C5B—C6B	0.0 (8)
C6B—C1B—C2B—C3B	0.0 (7)	C4B—C5B—C6B—C1B	0.0 (8)
C7—C1B—C2B—C3B	−179.2 (4)	C1B—C7—C8—C9	175.5 (2)
C2B—C1B—C6B—C5B	0.0 (8)	C7—C8—C9—N1	178.13 (13)
C7—C1B—C6B—C5B	179.1 (4)	C7—C8—C9—C10	−2.7 (2)

Cg1 and Cg2 are the centroids of the disordered benzene rings C1A –C6A and C1B–C6B, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1i	0.88	2.12	2.9785 (15)	166
N3—H3B···O1ii	0.88	2.08	2.9434 (14)	168
N3—H3C···N1	0.88	2.28	2.6397 (16)	104
C10—H10A···O1i	0.98	2.51	3.2384 (17)	131
C10—H10B···N1iii	0.98	2.58	3.4566 (19)	148
C4B—H4BA···Cg1iv	0.95	2.86	3.618 (5)	138
C4A—H4AA···Cg1iv	0.95	2.76	3.590 (5)	146
C4A—H4AA···Cg2iv	0.95	2.93	3.714 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the disordered benzene rings C1A –C6A and C1B–C6B, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1i	0.88	2.12	2.9785 (15)	166
N3—H3B⋯O1ii	0.88	2.08	2.9434 (14)	168
C10—H10A⋯O1i	0.98	2.51	3.2384 (17)	131
C10—H10B⋯N1iii	0.98	2.58	3.4566 (19)	148
C4B—H4BA⋯Cg1iv	0.95	2.86	3.618 (5)	138
C4A—H4AA⋯Cg1iv	0.95	2.76	3.590 (5)	146
C4A—H4AA⋯Cg2iv	0.95	2.93	3.714 (5)	141

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