(E,E)-1,2-Bis[3-(prop-2-yn-1-yl-oxy)benzyl-idene]hydrazine.

The mol-ecule of the title compound, C(20)H(16)N(2)O(2), is centrosymmetric, the inversion center being located at the mid-point of the central azine bond. The conformation around the C=N bond is E. The whole mol-ecule (except for the H atoms) is essentially planar, with an r.m.s. deviation of 0.07 Å. In the crystal, mol-ecules are linked head-to-tail by pairs of C-H⋯O hydrogen bonds, forming inversion dimers, and resulting in the formation of chains propagating along [011].

Related literature

For biological properties and practical appplications of diacetyl­ene compounds, see: Zloh et al. (2007 ▶); Buckley & Neumeister (1992 ▶). For the structure of (E,E)-1,2-bis­[3-(prop-2-yn-1-yl­oxy)benzyl­indene]­hydrazine see: Al-Mehana et al. (2011 ▶).

Experimental

Crystal data

C20H16N2O2

M = 316.35

Triclinic,

a = 4.5700 (3) Å

b = 9.4947 (7) Å

c = 9.8920 (8) Å

α = 67.986 (7)°

β = 77.487 (6)°

γ = 84.132 (6)°

V = 388.37 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.1 × 0.08 × 0.08 mm

Data collection

Agilent SuperNova Dual (Cu) Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.440, T max = 1.000

2956 measured reflections

1710 independent reflections

1508 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.02

1710 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: pubCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025524/su2430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025524/su2430Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025524/su2430Isup3.cml

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

C20H16N2O2	Z = 1
Mr = 316.35	F(000) = 166
Triclinic, P1	Dx = 1.353 Mg m−3
Hall symbol: -P 1	Melting point = 401–403 K
a = 4.5700 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4947 (7) Å	Cell parameters from 1636 reflections
c = 9.8920 (8) Å	θ = 2.3–29.1°
α = 67.986 (7)°	µ = 0.09 mm−1
β = 77.487 (6)°	T = 100 K
γ = 84.132 (6)°	Block, colourless
V = 388.37 (5) Å3	0.1 × 0.08 × 0.08 mm

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer	1710 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1508 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −5→4
Tmin = 0.440, Tmax = 1.000	k = −12→12
2956 measured reflections	l = −12→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0756P)2 + 0.0718P] where P = (Fo2 + 2Fc2)/3
1710 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 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 esds are taken into account in the estimation of distances, angles and torsion angles

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	0.26162 (18)	0.81143 (9)	0.53750 (8)	0.0186 (3)
N1	0.9141 (2)	0.53809 (10)	0.94457 (10)	0.0154 (3)
C1	0.1926 (3)	0.64779 (13)	0.28726 (13)	0.0223 (3)
C2	0.2727 (3)	0.67068 (13)	0.38360 (13)	0.0201 (3)
C3	0.3877 (3)	0.68058 (13)	0.50670 (13)	0.0202 (3)
C4	0.3322 (2)	0.82703 (12)	0.65948 (12)	0.0150 (3)
C5	0.1900 (3)	0.94943 (13)	0.69477 (13)	0.0173 (3)
C6	0.2352 (3)	0.97068 (12)	0.81942 (13)	0.0186 (3)
C7	0.4213 (3)	0.87082 (13)	0.90930 (13)	0.0176 (3)
C8	0.5677 (2)	0.75107 (12)	0.87209 (12)	0.0151 (3)
C9	0.5252 (2)	0.72894 (12)	0.74544 (12)	0.0148 (3)
C10	0.7639 (2)	0.65050 (12)	0.96900 (12)	0.0150 (3)
H1	0.13000	0.62990	0.21190	0.0270*
H3A	0.33630	0.59000	0.59440	0.0240*
H3B	0.60440	0.68700	0.48080	0.0240*
H5	0.06580	1.01620	0.63490	0.0210*
H6	0.14090	1.05210	0.84350	0.0220*
H7	0.44750	0.88440	0.99420	0.0210*
H9	0.62480	0.64970	0.71920	0.0180*
H10	0.78030	0.66930	1.05280	0.0180*

	U11	U22	U33	U12	U13	U23
O1	0.0223 (5)	0.0187 (4)	0.0173 (4)	0.0091 (3)	−0.0109 (3)	−0.0080 (3)
N1	0.0141 (5)	0.0152 (5)	0.0162 (5)	0.0017 (4)	−0.0086 (4)	−0.0022 (4)
C1	0.0254 (6)	0.0225 (6)	0.0209 (6)	0.0061 (5)	−0.0105 (5)	−0.0083 (5)
C2	0.0206 (6)	0.0183 (6)	0.0204 (6)	0.0069 (4)	−0.0071 (4)	−0.0061 (5)
C3	0.0218 (6)	0.0209 (6)	0.0208 (6)	0.0085 (5)	−0.0101 (5)	−0.0098 (5)
C4	0.0146 (5)	0.0156 (5)	0.0135 (5)	−0.0005 (4)	−0.0045 (4)	−0.0027 (4)
C5	0.0166 (6)	0.0146 (5)	0.0184 (6)	0.0037 (4)	−0.0076 (4)	−0.0021 (4)
C6	0.0205 (6)	0.0132 (5)	0.0225 (6)	0.0049 (4)	−0.0069 (5)	−0.0069 (4)
C7	0.0194 (6)	0.0170 (5)	0.0184 (5)	0.0014 (4)	−0.0082 (4)	−0.0065 (4)
C8	0.0126 (5)	0.0136 (5)	0.0175 (5)	−0.0001 (4)	−0.0050 (4)	−0.0028 (4)
C9	0.0142 (5)	0.0128 (5)	0.0166 (5)	0.0026 (4)	−0.0044 (4)	−0.0044 (4)
C10	0.0150 (5)	0.0152 (5)	0.0160 (5)	0.0000 (4)	−0.0067 (4)	−0.0050 (4)

O1—C3	1.4247 (16)	C8—C9	1.4009 (16)
O1—C4	1.3763 (13)	C8—C10	1.4649 (15)
N1—C10	1.2808 (15)	C1—H1	0.9300
N1—N1i	1.4158 (13)	C3—H3A	0.9700
C1—C2	1.1883 (18)	C3—H3B	0.9700
C2—C3	1.4632 (18)	C5—H5	0.9300
C4—C5	1.3951 (18)	C6—H6	0.9300
C4—C9	1.3899 (15)	C7—H7	0.9300
C5—C6	1.3817 (17)	C9—H9	0.9300
C6—C7	1.3941 (18)	C10—H10	0.9300
C7—C8	1.3883 (18)
C3—O1—C4	115.61 (9)	O1—C3—H3A	110.00
N1i—N1—C10	111.29 (9)	O1—C3—H3B	110.00
C1—C2—C3	173.13 (14)	C2—C3—H3A	110.00
O1—C3—C2	109.82 (11)	C2—C3—H3B	110.00
O1—C4—C5	115.01 (10)	H3A—C3—H3B	108.00
O1—C4—C9	124.05 (11)	C4—C5—H5	120.00
C5—C4—C9	120.93 (11)	C6—C5—H5	120.00
C4—C5—C6	119.44 (12)	C5—C6—H6	120.00
C5—C6—C7	120.38 (12)	C7—C6—H6	120.00
C6—C7—C8	120.04 (11)	C6—C7—H7	120.00
C7—C8—C9	120.09 (10)	C8—C7—H7	120.00
C7—C8—C10	117.97 (10)	C4—C9—H9	120.00
C9—C8—C10	121.94 (10)	C8—C9—H9	120.00
C4—C9—C8	119.08 (11)	N1—C10—H10	118.00
N1—C10—C8	123.54 (10)	C8—C10—H10	118.00
C2—C1—H1	180.00
C3—O1—C4—C9	3.31 (15)	C4—C5—C6—C7	0.0 (2)
C4—O1—C3—C2	174.74 (10)	C5—C6—C7—C8	1.4 (2)
C3—O1—C4—C5	−175.53 (10)	C6—C7—C8—C10	179.20 (11)
C10—N1—N1i—C10i	179.98 (10)	C6—C7—C8—C9	−0.97 (18)
N1i—N1—C10—C8	179.47 (9)	C7—C8—C9—C4	−0.85 (16)
O1—C4—C5—C6	177.00 (11)	C7—C8—C10—N1	−178.79 (11)
C9—C4—C5—C6	−1.88 (18)	C9—C8—C10—N1	1.38 (17)
C5—C4—C9—C8	2.29 (16)	C10—C8—C9—C4	178.97 (10)
O1—C4—C9—C8	−176.49 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ii	0.93	2.52	3.4467 (16)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.52	3.4467 (16)	177

Symmetry code: (i) .