(E,E)-1,2-Bis[4-(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 with the mid-point of the central N-N bond located on an inversion center. The configuration around the C=N bond is E. The whole mol-ecule (except for the H atoms) is approximately planar, with an r.m.s. deviation of 0.07 Å. In the crystal, the presence of weak inter-molecular C-H⋯O hydrogen bonding involving each acetyl-ene H atom and the adjacent phen-oxy O atom results in the formation of supra-molecular chains.

Related literature

For the structure of (E,E)-1,2-bis­[3-meth­oxy-4-(prop-2-yn-1-yl­oxy)benzyl­indene]­hydrazine see: Al-Mehana et al. (2011 ▶).

Experimental

Crystal data

C20H16N2O2

M = 316.35

Monoclinic,

a = 7.6598 (1) Å

b = 8.1117 (1) Å

c = 12.9966 (2) Å

β = 94.466 (1)°

V = 805.08 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.16 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.996

7404 measured reflections

1847 independent reflections

1698 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.111

S = 1.01

1847 reflections

113 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104102X/xu5328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104102X/xu5328Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104102X/xu5328Isup3.cml

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

C20H16N2O2	F(000) = 332
Mr = 316.35	Dx = 1.305 Mg m−3
Monoclinic, P21/n	Melting point: 453 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.6598 (1) Å	Cell parameters from 4790 reflections
b = 8.1117 (1) Å	θ = 3.0–28.3°
c = 12.9966 (2) Å	µ = 0.09 mm−1
β = 94.466 (1)°	T = 100 K
V = 805.08 (2) Å3	Block, yellow
Z = 2	0.30 × 0.16 × 0.05 mm

Bruker APEXII CCD area-detector diffractometer	1847 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.975, Tmax = 0.996	k = −10→10
7404 measured reflections	l = −16→16

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0717P)2 + 0.215P] where P = (Fo2 + 2Fc2)/3
1847 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.26 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
O1	0.03607 (9)	0.22226 (8)	0.83985 (5)	0.0188 (2)
N1	0.44709 (10)	−0.44532 (10)	0.96895 (6)	0.0200 (2)
C1	−0.20330 (14)	0.57486 (13)	0.80143 (8)	0.0249 (2)
H1	−0.285 (2)	0.6468 (19)	0.7698 (12)	0.040 (4)*
C2	−0.09922 (13)	0.48192 (12)	0.84201 (7)	0.0198 (2)
C3	0.02396 (12)	0.37108 (11)	0.89870 (7)	0.0185 (2)
H3A	0.1381	0.4229	0.9089	0.022*
H3B	−0.0166	0.3462	0.9658	0.022*
C4	0.13140 (11)	0.09661 (11)	0.88750 (7)	0.0165 (2)
C5	0.14991 (13)	−0.04424 (12)	0.82692 (7)	0.0196 (2)
H5	0.1006	−0.0473	0.7592	0.024*
C6	0.24152 (12)	−0.17843 (12)	0.86805 (7)	0.0192 (2)
H6	0.2533	−0.2721	0.8279	0.023*
C7	0.31723 (12)	−0.17477 (11)	0.97012 (7)	0.0179 (2)
C8	0.29749 (12)	−0.03295 (12)	1.02859 (7)	0.0186 (2)
H8	0.3473	−0.0293	1.0961	0.022*
C9	0.20532 (12)	0.10295 (12)	0.98860 (7)	0.0181 (2)
H9	0.1932	0.1966	1.0287	0.022*
C10	0.42043 (12)	−0.31051 (12)	1.01685 (7)	0.0188 (2)
H10	0.4689	−0.2987	1.0843	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0219 (4)	0.0157 (4)	0.0182 (3)	0.0023 (2)	−0.0021 (3)	−0.0015 (2)
N1	0.0182 (4)	0.0175 (4)	0.0238 (4)	0.0006 (3)	−0.0008 (3)	0.0045 (3)
C1	0.0271 (5)	0.0247 (5)	0.0224 (5)	0.0053 (4)	−0.0016 (4)	−0.0010 (4)
C2	0.0215 (5)	0.0192 (5)	0.0187 (4)	−0.0009 (4)	0.0008 (3)	−0.0028 (3)
C3	0.0198 (5)	0.0161 (4)	0.0191 (4)	0.0004 (3)	−0.0011 (3)	−0.0021 (3)
C4	0.0146 (4)	0.0155 (4)	0.0195 (5)	−0.0007 (3)	0.0014 (3)	0.0018 (3)
C5	0.0216 (5)	0.0197 (5)	0.0173 (4)	−0.0006 (3)	−0.0001 (3)	−0.0008 (3)
C6	0.0211 (5)	0.0159 (4)	0.0207 (5)	−0.0002 (3)	0.0021 (3)	−0.0014 (3)
C7	0.0162 (4)	0.0169 (5)	0.0208 (5)	−0.0013 (3)	0.0028 (3)	0.0028 (3)
C8	0.0175 (4)	0.0204 (5)	0.0176 (4)	−0.0020 (3)	0.0001 (3)	0.0012 (3)
C9	0.0183 (5)	0.0171 (4)	0.0191 (4)	−0.0011 (3)	0.0019 (3)	−0.0017 (3)
C10	0.0166 (4)	0.0192 (5)	0.0205 (4)	−0.0019 (3)	0.0009 (3)	0.0030 (3)

O1—C4	1.3730 (11)	C5—C4	1.4010 (13)
O1—C3	1.4359 (11)	C5—H5	0.9300
N1—C10	1.2825 (13)	C6—H6	0.9300
N1—N1i	1.4120 (15)	C7—C8	1.3934 (13)
C1—H1	0.929 (16)	C7—C6	1.4062 (13)
C2—C1	1.1902 (15)	C8—C9	1.3881 (13)
C2—C3	1.4606 (13)	C8—H8	0.9300
C3—H3A	0.9700	C9—H9	0.9300
C3—H3B	0.9700	C10—C7	1.4599 (13)
C4—C9	1.3906 (13)	C10—H10	0.9300
C5—C6	1.3800 (13)
O1—C4—C9	124.18 (8)	C5—C6—H6	119.7
O1—C4—C5	115.18 (8)	C6—C7—C10	123.14 (9)
O1—C3—C2	108.35 (7)	C6—C5—C4	119.75 (9)
O1—C3—H3A	110.0	C6—C5—H5	120.1
O1—C3—H3B	110.0	C7—C6—H6	119.7
N1—C10—C7	122.86 (9)	C7—C10—H10	118.6
N1—C10—H10	118.6	C7—C8—H8	119.2
C1—C2—C3	176.00 (10)	C8—C9—C4	118.83 (9)
C2—C3—H3A	110.0	C8—C9—H9	120.6
C2—C3—H3B	110.0	C8—C7—C6	118.53 (9)
C2—C1—H1	179.5 (10)	C8—C7—C10	118.30 (8)
H3A—C3—H3B	108.4	C9—C4—C5	120.63 (9)
C4—C5—H5	120.1	C9—C8—C7	121.68 (9)
C4—O1—C3	115.98 (7)	C9—C8—H8	119.2
C4—C9—H9	120.6	C10—N1—N1i	111.36 (10)
C5—C6—C7	120.57 (9)
O1—C4—C9—C8	179.33 (8)	C5—C4—C9—C8	−0.16 (13)
N1i—N1—C10—C7	179.14 (9)	C6—C5—C4—O1	−179.17 (8)
N1—C10—C7—C8	−179.44 (9)	C6—C5—C4—C9	0.36 (14)
N1—C10—C7—C6	−1.46 (15)	C6—C7—C8—C9	0.16 (14)
C1—C2—C3—O1	140.8 (15)	C7—C8—C9—C4	−0.10 (14)
C3—O1—C4—C9	3.86 (13)	C8—C7—C6—C5	0.05 (14)
C3—O1—C4—C5	−176.63 (7)	C10—C7—C8—C9	178.23 (8)
C4—O1—C3—C2	−172.83 (7)	C10—C7—C6—C5	−177.92 (8)
C4—C5—C6—C7	−0.31 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ii	0.928 (15)	2.383 (15)	3.2511 (13)	155.7 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.928 (15)	2.383 (15)	3.2511 (13)	155.7 (13)

Symmetry code: (i) .