(1E,2E)-1,2-Bis(2,3-dihydro-1H-inden-1-yl-idene)hydrazine.

In the title compound, C(18)H(16)N(2), there are two independent half-mol-ecules (A and B) in the asymmetric unit, each mol-ecule being completed by an inversion center situated in the mid-point of the central N-N bond. The mol-ecules themselves therefore are essentially planar with r.m.s. deviations of 0.015 (1) and 0.020 (1) Å, respectively. In the crystal, mol-ecules are connected via C-H⋯π inter-actions in which only type B mol-ecules are donors, while both A and B mol-ecules act as acceptors. As a result, type B mol-ecules are linked into infinite chains along b, which are inter-connected by molecules of type A.

Related literature

For structural and physical properties of indanone-derived azines, see: Choytun et al. (2004 ▶). For the reactivity of azines towards Fe2(CO)9, see: Dönnecke et al. (2004a ▶,b ▶); Wu et al. (2006 ▶).

Experimental

Crystal data

C18H16N2

M = 260.33

Triclinic,

a = 5.1161 (10) Å

b = 11.877 (2) Å

c = 12.245 (2) Å

α = 109.59 (3)°

β = 99.93 (3)°

γ = 100.47 (3)°

V = 667.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 183 K

0.6 × 0.1 × 0.1 mm

Data collection

Nonius KappaCCD diffractometer

4726 measured reflections

2999 independent reflections

1901 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.114

S = 1.02

2999 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203560X/bg2471sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203560X/bg2471Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203560X/bg2471Isup3.mol

Supplementary material file. DOI: 10.1107/S160053681203560X/bg2471Isup4.mol

Supplementary material file. DOI: 10.1107/S160053681203560X/bg2471Isup5.cml

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

C18H16N2	Z = 2
Mr = 260.33	F(000) = 276
Triclinic, P1	Dx = 1.296 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1161 (10) Å	Cell parameters from 4726 reflections
b = 11.877 (2) Å	θ = 1.8–27.5°
c = 12.245 (2) Å	µ = 0.08 mm−1
α = 109.59 (3)°	T = 183 K
β = 99.93 (3)°	Quader, yellow
γ = 100.47 (3)°	0.6 × 0.1 × 0.1 mm
V = 667.1 (2) Å3

Nonius KappaCCD diffractometer	1901 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
phi–scan, ω–scan	h = −6→6
4726 measured reflections	k = −14→15
2999 independent reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
2999 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 e Å−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
N1	0.0535 (2)	0.51077 (11)	0.95393 (11)	0.0280 (3)
C1	0.3116 (3)	0.50842 (14)	0.74721 (14)	0.0304 (4)
H1	0.2287	0.5754	0.7683	0.036*
C2	0.4487 (3)	0.49064 (14)	0.65753 (14)	0.0338 (4)
H2	0.4614	0.5461	0.6168	0.041*
N2	0.0565 (3)	−0.00657 (12)	0.45007 (11)	0.0319 (3)
C3	0.5684 (3)	0.39184 (14)	0.62645 (14)	0.0326 (4)
H3	0.6627	0.3807	0.5648	0.039*
C4	0.5518 (3)	0.30961 (14)	0.68430 (14)	0.0309 (4)
H4	0.6330	0.2421	0.6624	0.037*
C5	0.4150 (3)	0.32704 (13)	0.77458 (13)	0.0243 (4)
C6	0.2971 (3)	0.42640 (13)	0.80617 (13)	0.0238 (3)
C7	0.1704 (3)	0.42645 (13)	0.90464 (13)	0.0237 (3)
C8	0.2091 (3)	0.31658 (13)	0.93521 (14)	0.0276 (4)
H8B	0.0291	0.2597	0.9222	0.033*
H8A	0.3110	0.3439	1.0199	0.033*
C9	0.3745 (3)	0.25193 (13)	0.85068 (14)	0.0291 (4)
H9B	0.5534	0.2519	0.8969	0.035*
H9A	0.2712	0.1654	0.8005	0.035*
C10	0.1242 (3)	0.20212 (14)	0.17948 (13)	0.0314 (4)
H10	0.0774	0.2678	0.1594	0.038*
C11	0.2587 (3)	0.12604 (15)	0.11147 (15)	0.0365 (4)
H11	0.3040	0.1397	0.0441	0.044*
C12	0.3292 (3)	0.02931 (15)	0.13998 (14)	0.0356 (4)
H12	0.4231	−0.0217	0.0924	0.043*
C13	0.2633 (3)	0.00749 (14)	0.23669 (14)	0.0302 (4)
H13	0.3104	−0.0583	0.2565	0.036*
C14	0.1258 (3)	0.08405 (13)	0.30495 (13)	0.0250 (3)
C15	0.0581 (3)	0.18161 (13)	0.27746 (13)	0.0259 (4)
C16	−0.0860 (3)	0.25116 (13)	0.36545 (14)	0.0302 (4)
H16B	−0.2718	0.2490	0.3237	0.036*
H16A	0.0203	0.3385	0.4089	0.036*
C17	−0.1032 (3)	0.18309 (14)	0.45227 (14)	0.0289 (4)
H17B	−0.0041	0.2396	0.5352	0.035*
H17A	−0.2971	0.1508	0.4506	0.035*
C18	0.0289 (3)	0.07840 (13)	0.40943 (13)	0.0250 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0332 (7)	0.0306 (7)	0.0251 (7)	0.0124 (6)	0.0151 (6)	0.0108 (6)
C1	0.0360 (9)	0.0302 (9)	0.0310 (9)	0.0135 (7)	0.0142 (7)	0.0136 (7)
C2	0.0429 (10)	0.0356 (9)	0.0322 (9)	0.0135 (8)	0.0172 (8)	0.0190 (8)
N2	0.0459 (8)	0.0310 (7)	0.0301 (8)	0.0157 (6)	0.0198 (6)	0.0174 (6)
C3	0.0365 (9)	0.0392 (9)	0.0297 (9)	0.0143 (7)	0.0183 (8)	0.0150 (8)
C4	0.0328 (9)	0.0349 (9)	0.0317 (9)	0.0171 (7)	0.0162 (7)	0.0126 (8)
C5	0.0221 (7)	0.0268 (8)	0.0242 (8)	0.0068 (6)	0.0072 (7)	0.0091 (7)
C6	0.0251 (8)	0.0236 (7)	0.0223 (8)	0.0061 (6)	0.0079 (6)	0.0073 (6)
C7	0.0223 (7)	0.0238 (8)	0.0233 (8)	0.0059 (6)	0.0063 (6)	0.0066 (6)
C8	0.0298 (8)	0.0270 (8)	0.0289 (9)	0.0080 (7)	0.0120 (7)	0.0115 (7)
C9	0.0311 (8)	0.0280 (8)	0.0325 (9)	0.0116 (7)	0.0123 (7)	0.0125 (7)
C10	0.0423 (9)	0.0325 (9)	0.0300 (9)	0.0151 (7)	0.0142 (8)	0.0195 (8)
C11	0.0509 (10)	0.0400 (9)	0.0322 (9)	0.0170 (8)	0.0226 (8)	0.0219 (8)
C12	0.0476 (10)	0.0350 (9)	0.0333 (10)	0.0187 (8)	0.0227 (8)	0.0141 (8)
C13	0.0377 (9)	0.0265 (8)	0.0310 (9)	0.0112 (7)	0.0137 (7)	0.0126 (7)
C14	0.0261 (8)	0.0256 (8)	0.0229 (8)	0.0052 (6)	0.0064 (6)	0.0092 (7)
C15	0.0284 (8)	0.0268 (8)	0.0243 (8)	0.0078 (6)	0.0084 (7)	0.0106 (7)
C16	0.0368 (9)	0.0296 (8)	0.0318 (9)	0.0154 (7)	0.0131 (7)	0.0152 (7)
C17	0.0321 (8)	0.0325 (8)	0.0271 (8)	0.0126 (7)	0.0110 (7)	0.0136 (7)
C18	0.0267 (8)	0.0248 (8)	0.0242 (8)	0.0070 (6)	0.0070 (7)	0.0096 (7)

N1—C7	1.2895 (18)	C9—H9B	0.9900
N1—N1i	1.412 (2)	C9—H9A	0.9900
C1—C2	1.381 (2)	C10—C11	1.379 (2)
C1—C6	1.393 (2)	C10—C15	1.385 (2)
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.393 (2)	C11—C12	1.396 (2)
C2—H2	0.9500	C11—H11	0.9500
N2—C18	1.2847 (19)	C12—C13	1.377 (2)
N2—N2ii	1.415 (2)	C12—H12	0.9500
C3—C4	1.385 (2)	C13—C14	1.395 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.386 (2)	C14—C15	1.394 (2)
C4—H4	0.9500	C14—C18	1.467 (2)
C5—C6	1.393 (2)	C15—C16	1.512 (2)
C5—C9	1.505 (2)	C16—C17	1.541 (2)
C6—C7	1.464 (2)	C16—H16B	0.9900
C7—C8	1.509 (2)	C16—H16A	0.9900
C8—C9	1.544 (2)	C17—C18	1.506 (2)
C8—H8B	0.9900	C17—H17B	0.9900
C8—H8A	0.9900	C17—H17A	0.9900
C7—N1—N1i	111.59 (15)	H9B—C9—H9A	108.9
C2—C1—C6	118.82 (14)	C11—C10—C15	119.20 (14)
C2—C1—H1	120.6	C11—C10—H10	120.4
C6—C1—H1	120.6	C15—C10—H10	120.4
C1—C2—C3	120.35 (15)	C10—C11—C12	121.08 (15)
C1—C2—H2	119.8	C10—C11—H11	119.5
C3—C2—H2	119.8	C12—C11—H11	119.5
C18—N2—N2ii	111.52 (15)	C13—C12—C11	120.29 (15)
C4—C3—C2	120.84 (14)	C13—C12—H12	119.9
C4—C3—H3	119.6	C11—C12—H12	119.9
C2—C3—H3	119.6	C12—C13—C14	118.55 (15)
C5—C4—C3	119.13 (14)	C12—C13—H13	120.7
C5—C4—H4	120.4	C14—C13—H13	120.7
C3—C4—H4	120.4	C13—C14—C15	121.22 (14)
C4—C5—C6	119.98 (14)	C13—C14—C18	128.93 (15)
C4—C5—C9	128.68 (13)	C15—C14—C18	109.84 (13)
C6—C5—C9	111.34 (12)	C10—C15—C14	119.64 (14)
C1—C6—C5	120.89 (14)	C10—C15—C16	129.42 (14)
C1—C6—C7	129.37 (14)	C14—C15—C16	110.94 (13)
C5—C6—C7	109.75 (13)	C15—C16—C17	104.84 (12)
N1—C7—C6	122.75 (14)	C15—C16—H16B	110.8
N1—C7—C8	128.85 (14)	C17—C16—H16B	110.8
C6—C7—C8	108.39 (12)	C15—C16—H16A	110.8
C7—C8—C9	105.79 (12)	C17—C16—H16A	110.8
C7—C8—H8B	110.6	H16B—C16—H16A	108.9
C9—C8—H8B	110.6	C18—C17—C16	105.91 (12)
C7—C8—H8A	110.6	C18—C17—H17B	110.6
C9—C8—H8A	110.6	C16—C17—H17B	110.6
H8B—C8—H8A	108.7	C18—C17—H17A	110.6
C5—C9—C8	104.71 (12)	C16—C17—H17A	110.6
C5—C9—H9B	110.8	H17B—C17—H17A	108.7
C8—C9—H9B	110.8	N2—C18—C14	122.08 (14)
C5—C9—H9A	110.8	N2—C18—C17	129.46 (14)
C8—C9—H9A	110.8	C14—C18—C17	108.45 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···Cg1	0.99	2.76	3.687 (3)	157
C16—H16B···Cg2iii	0.99	2.79	3.649 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯Cg1	0.99	2.76	3.687 (3)	157
C16—H16B⋯Cg2i	0.99	2.79	3.649 (2)	146

Symmetry code: (i) .