(E)-2-Cyano-N'-(1,2,3,4-tetra-hydro-naphthalen-1-yl-idene)acetohydrazide.

In the title compound, C(13)H(13)N(3)O, the tetra-hydro-benzene ring adopts a half-boat (envelope) conformation. The mean plane of the tetra-hydro-naphthalene ring system forms a dihedral angle of 9.56 (6)° with the mean plane of the cyano-acetohydrazide group. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops. The dimers are connected by C-H⋯N hydrogen bonds into a chain propagating along [101]. The crystal packing also features C-H⋯π inter-actions.

Related literature

For background to tetra­lin, see: Dutta et al. (2002 ▶); Taddei et al. (2002 ▶); Zaghary et al. (2005 ▶); Bahgat & Khalifa (2006 ▶); El Nezhawy et al. (2009 ▶); Khalifa et al. (2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H13N3O

M = 227.26

Triclinic,

a = 7.6414 (1) Å

b = 7.6748 (1) Å

c = 10.5644 (2) Å

α = 109.589 (1)°

β = 91.405 (1)°

γ = 93.260 (1)°

V = 582.13 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.69 mm−1

T = 296 K

0.59 × 0.51 × 0.40 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.687, T max = 0.771

5749 measured reflections

1898 independent reflections

1762 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.05

1898 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202106X/hb6781sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202106X/hb6781Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202106X/hb6781Isup3.cml

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

C13H13N3O	Z = 2
Mr = 227.26	F(000) = 240
Triclinic, P1	Dx = 1.297 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.6414 (1) Å	Cell parameters from 2725 reflections
b = 7.6748 (1) Å	θ = 5.8–70.2°
c = 10.5644 (2) Å	µ = 0.69 mm−1
α = 109.589 (1)°	T = 296 K
β = 91.405 (1)°	Block, colourless
γ = 93.260 (1)°	0.59 × 0.51 × 0.40 mm
V = 582.13 (2) Å3

Bruker SMART APEXII CCD diffractometer	1898 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 65.0°, θmin = 5.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.687, Tmax = 0.771	k = −7→9
5749 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.0904P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1898 reflections	Δρmax = 0.18 e Å−3
159 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (3)

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
O1	0.19129 (16)	0.4167 (2)	0.53245 (10)	0.0798 (4)
N1	0.07938 (15)	0.36666 (18)	0.32370 (11)	0.0530 (3)
N2	0.10531 (14)	0.29801 (15)	0.18782 (10)	0.0456 (3)
N3	0.5764 (3)	0.2338 (4)	0.5360 (2)	0.1264 (9)
C1	−0.02329 (16)	0.29510 (17)	0.10641 (13)	0.0419 (3)
C2	−0.20191 (18)	0.3606 (2)	0.14809 (15)	0.0531 (4)
H2A	−0.1954	0.4950	0.1788	0.064*
H2B	−0.2357	0.3218	0.2230	0.064*
C3	−0.34209 (18)	0.2862 (2)	0.03515 (16)	0.0590 (4)
H3A	−0.3665	0.1544	0.0168	0.071*
H3B	−0.4494	0.3470	0.0632	0.071*
C4	−0.28501 (19)	0.3183 (2)	−0.09133 (16)	0.0583 (4)
H4A	−0.2742	0.4504	−0.0759	0.070*
H4B	−0.3738	0.2621	−0.1629	0.070*
C5	−0.11171 (18)	0.23730 (19)	−0.13436 (14)	0.0491 (4)
C6	0.01244 (16)	0.22607 (16)	−0.03809 (12)	0.0416 (3)
C7	0.17256 (17)	0.15242 (19)	−0.08101 (14)	0.0478 (3)
H7A	0.2555	0.1441	−0.0177	0.057*
C8	0.2098 (2)	0.0923 (2)	−0.21424 (15)	0.0575 (4)
H8A	0.3170	0.0438	−0.2407	0.069*
C9	0.0876 (2)	0.1038 (2)	−0.30948 (15)	0.0636 (4)
H9A	0.1122	0.0629	−0.4001	0.076*
C10	−0.0706 (2)	0.1761 (2)	−0.26907 (15)	0.0613 (4)
H10A	−0.1520	0.1842	−0.3334	0.074*
C11	0.20438 (19)	0.3556 (2)	0.41121 (14)	0.0547 (4)
C12	0.3655 (2)	0.2592 (2)	0.35112 (15)	0.0619 (4)
H12A	0.3304	0.1361	0.2892	0.074*
H12B	0.4251	0.3284	0.3011	0.074*
C13	0.4837 (2)	0.2454 (3)	0.45556 (17)	0.0712 (5)
H1N1	−0.010 (3)	0.434 (3)	0.3642 (19)	0.078 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0795 (8)	0.1259 (11)	0.0388 (6)	0.0515 (7)	0.0104 (5)	0.0263 (6)
N1	0.0473 (7)	0.0739 (8)	0.0390 (6)	0.0203 (6)	0.0055 (5)	0.0178 (5)
N2	0.0432 (6)	0.0558 (7)	0.0378 (6)	0.0092 (5)	0.0022 (4)	0.0148 (5)
N3	0.0968 (14)	0.189 (2)	0.0923 (14)	0.0546 (15)	−0.0274 (11)	0.0414 (14)
C1	0.0377 (7)	0.0438 (7)	0.0456 (7)	0.0036 (5)	0.0000 (5)	0.0167 (5)
C2	0.0420 (7)	0.0643 (9)	0.0538 (8)	0.0104 (6)	0.0054 (6)	0.0195 (7)
C3	0.0374 (7)	0.0665 (9)	0.0744 (10)	0.0053 (6)	−0.0015 (6)	0.0255 (8)
C4	0.0441 (8)	0.0667 (9)	0.0653 (9)	0.0060 (6)	−0.0122 (6)	0.0245 (7)
C5	0.0452 (7)	0.0495 (7)	0.0512 (8)	0.0002 (6)	−0.0089 (6)	0.0164 (6)
C6	0.0395 (7)	0.0401 (6)	0.0429 (7)	0.0007 (5)	−0.0037 (5)	0.0117 (5)
C7	0.0438 (7)	0.0517 (7)	0.0450 (7)	0.0076 (6)	−0.0041 (5)	0.0122 (6)
C8	0.0544 (8)	0.0603 (9)	0.0503 (8)	0.0106 (7)	0.0047 (6)	0.0078 (7)
C9	0.0711 (10)	0.0723 (10)	0.0396 (7)	0.0049 (8)	−0.0002 (7)	0.0089 (7)
C10	0.0632 (9)	0.0711 (10)	0.0466 (8)	0.0019 (7)	−0.0144 (7)	0.0174 (7)
C11	0.0542 (8)	0.0729 (9)	0.0398 (7)	0.0209 (7)	0.0061 (6)	0.0197 (6)
C12	0.0528 (8)	0.0840 (11)	0.0442 (8)	0.0228 (7)	0.0006 (6)	0.0127 (7)
C13	0.0574 (9)	0.0923 (12)	0.0596 (9)	0.0241 (8)	−0.0055 (8)	0.0175 (9)

O1—C11	1.2163 (17)	C4—H4B	0.9700
N1—C11	1.3389 (18)	C5—C10	1.391 (2)
N1—N2	1.3770 (15)	C5—C6	1.4009 (18)
N1—H1N1	0.90 (2)	C6—C7	1.3986 (19)
N2—C1	1.2841 (16)	C7—C8	1.369 (2)
N3—C13	1.122 (2)	C7—H7A	0.9300
C1—C6	1.4766 (18)	C8—C9	1.383 (2)
C1—C2	1.5061 (18)	C8—H8A	0.9300
C2—C3	1.519 (2)	C9—C10	1.376 (2)
C2—H2A	0.9700	C9—H9A	0.9300
C2—H2B	0.9700	C10—H10A	0.9300
C3—C4	1.508 (2)	C11—C12	1.5140 (19)
C3—H3A	0.9700	C12—C13	1.444 (2)
C3—H3B	0.9700	C12—H12A	0.9700
C4—C5	1.510 (2)	C12—H12B	0.9700
C4—H4A	0.9700
C11—N1—N2	119.64 (11)	C6—C5—C4	120.20 (13)
C11—N1—H1N1	112.9 (12)	C7—C6—C5	118.82 (12)
N2—N1—H1N1	127.0 (12)	C7—C6—C1	120.57 (11)
C1—N2—N1	117.97 (11)	C5—C6—C1	120.59 (11)
N2—C1—C6	116.02 (11)	C8—C7—C6	121.36 (12)
N2—C1—C2	124.94 (12)	C8—C7—H7A	119.3
C6—C1—C2	119.01 (11)	C6—C7—H7A	119.3
C1—C2—C3	112.97 (12)	C7—C8—C9	119.94 (13)
C1—C2—H2A	109.0	C7—C8—H8A	120.0
C3—C2—H2A	109.0	C9—C8—H8A	120.0
C1—C2—H2B	109.0	C10—C9—C8	119.50 (14)
C3—C2—H2B	109.0	C10—C9—H9A	120.3
H2A—C2—H2B	107.8	C8—C9—H9A	120.3
C4—C3—C2	111.41 (12)	C9—C10—C5	121.62 (13)
C4—C3—H3A	109.3	C9—C10—H10A	119.2
C2—C3—H3A	109.3	C5—C10—H10A	119.2
C4—C3—H3B	109.3	O1—C11—N1	122.97 (13)
C2—C3—H3B	109.3	O1—C11—C12	120.79 (13)
H3A—C3—H3B	108.0	N1—C11—C12	116.23 (12)
C3—C4—C5	111.56 (12)	C13—C12—C11	110.54 (13)
C3—C4—H4A	109.3	C13—C12—H12A	109.5
C5—C4—H4A	109.3	C11—C12—H12A	109.5
C3—C4—H4B	109.3	C13—C12—H12B	109.5
C5—C4—H4B	109.3	C11—C12—H12B	109.5
H4A—C4—H4B	108.0	H12A—C12—H12B	108.1
C10—C5—C6	118.76 (13)	N3—C13—C12	179.4 (2)
C10—C5—C4	121.04 (12)
C11—N1—N2—C1	173.62 (13)	C2—C1—C6—C7	−175.60 (12)
N1—N2—C1—C6	178.06 (11)	N2—C1—C6—C5	−172.51 (11)
N1—N2—C1—C2	−0.3 (2)	C2—C1—C6—C5	5.95 (18)
N2—C1—C2—C3	−161.63 (13)	C5—C6—C7—C8	0.2 (2)
C6—C1—C2—C3	20.06 (18)	C1—C6—C7—C8	−178.26 (12)
C1—C2—C3—C4	−50.51 (17)	C6—C7—C8—C9	0.0 (2)
C2—C3—C4—C5	55.23 (17)	C7—C8—C9—C10	0.1 (2)
C3—C4—C5—C10	151.26 (14)	C8—C9—C10—C5	−0.4 (3)
C3—C4—C5—C6	−30.03 (18)	C6—C5—C10—C9	0.6 (2)
C10—C5—C6—C7	−0.5 (2)	C4—C5—C10—C9	179.32 (15)
C4—C5—C6—C7	−179.24 (12)	N2—N1—C11—O1	178.53 (15)
C10—C5—C6—C1	177.98 (12)	N2—N1—C11—C12	−2.2 (2)
C4—C5—C6—C1	−0.76 (19)	O1—C11—C12—C13	3.3 (2)
N2—C1—C6—C7	5.94 (18)	N1—C11—C12—C13	−175.97 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.91 (2)	1.96 (2)	2.8640 (17)	174.7 (19)
C10—H10A···N3ii	0.93	2.58	3.491 (3)	167
C2—H2A···Cg1iii	0.97	2.80	3.6775 (17)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.91 (2)	1.96 (2)	2.8640 (17)	174.7 (19)
C10—H10A⋯N3ii	0.93	2.58	3.491 (3)	167
C2—H2A⋯Cg1iii	0.97	2.80	3.6775 (17)	152

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