4-(Prop-2-yn-1-yl-oxy)benzene-1,2-dicarbonitrile.

In the title compound, C(11)H(6)N(2)O, the complete mol-ecule is generated by the application of crystallographic twofold symmetry (the mol-ecule is disordered about this axis). The prop-2-yn-1-yl residue is slightly twisted out of the plane of the benzene ring [C-O-C-C torsion angle = 173.1 (3)°] and is orientated away from the nitrile substituents. In the crystal, supra-molecular chains along the a axis, arising from C-H⋯N inter-actions, are connected into stacks along the c axis by π-π inter-actions between the benzene rings [centroid-centroid distance = 3.6978 (6) Å = length of the c axis].

Related literature

For the solubilization and some applications of phthanocyanine dyes, see: Jiang et al. (2011 ▶); Sleven et al. (2001 ▶). For the synthesis of substituted phthalonitriles, see: Wöhrle et al. (1993 ▶); Wu et al. (1998 ▶); Li & Lieberman (2001 ▶); Sleven et al. (2001 ▶); Li et al. (2008 ▶); Seven et al. (2009 ▶); Foo et al. (2012 ▶).

Experimental

Crystal data

C11H6N2O

M = 182.18

Monoclinic,

a = 11.4809 (9) Å

b = 22.2091 (16) Å

c = 3.6978 (6) Å

β = 91.304 (10)°

V = 942.62 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.15 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.792, T max = 1.000

3258 measured reflections

1114 independent reflections

840 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.163

S = 1.08

1114 reflections

86 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.28 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028309/hb6862sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028309/hb6862Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028309/hb6862Isup3.cml

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

C11H6N2O	F(000) = 376
Mr = 182.18	Dx = 1.284 Mg m−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 938 reflections
a = 11.4809 (9) Å	θ = 3.3–27.5°
b = 22.2091 (16) Å	µ = 0.09 mm−1
c = 3.6978 (6) Å	T = 100 K
β = 91.304 (10)°	Prism, colourless
V = 942.62 (18) Å3	0.15 × 0.05 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	1114 independent reflections
Radiation source: fine-focus sealed tube	840 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −26→28
Tmin = 0.792, Tmax = 1.000	l = −4→4
3258 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0718P)2 + 0.8054P] where P = (Fo2 + 2Fc2)/3
1114 reflections	(Δ/σ)max < 0.001
86 parameters	Δρmax = 0.41 e Å−3
12 restraints	Δρmin = −0.28 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	Occ. (<1)
O1	0.1308 (2)	0.45076 (11)	0.1768 (8)	0.0273 (7)	0.50
N1	0.15188 (16)	0.19174 (9)	0.2675 (6)	0.0376 (6)
C1	0.10982 (16)	0.23658 (9)	0.1829 (6)	0.0260 (5)
C2	0.05529 (16)	0.29272 (8)	0.0857 (5)	0.0219 (5)
C3	0.1103 (2)	0.34676 (10)	0.1663 (6)	0.0349 (6)
H3	0.1853	0.3469	0.2801	0.042*
C4	0.0555 (3)	0.40028 (10)	0.0803 (7)	0.0446 (7)
H4	0.0936	0.4374	0.1309	0.054*	0.50
C5	0.2499 (3)	0.44609 (17)	0.3108 (13)	0.0274 (10)	0.50
H5A	0.2962	0.4211	0.1458	0.033*	0.50
H5B	0.2522	0.4272	0.5535	0.033*	0.50
C6	0.2980 (3)	0.5082 (7)	0.3303 (12)	0.030 (3)	0.50
C7	0.3440 (4)	0.5544 (2)	0.3459 (17)	0.0463 (14)	0.50
H7	0.386 (5)	0.595 (3)	0.363 (16)	0.054 (16)*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0258 (13)	0.0187 (12)	0.0370 (15)	0.0001 (10)	−0.0069 (11)	−0.0008 (11)
N1	0.0332 (10)	0.0410 (11)	0.0383 (12)	0.0126 (9)	−0.0029 (8)	0.0074 (9)
C1	0.0191 (9)	0.0345 (12)	0.0242 (11)	−0.0003 (8)	−0.0019 (8)	0.0004 (8)
C2	0.0206 (10)	0.0234 (10)	0.0217 (10)	−0.0009 (7)	−0.0001 (8)	−0.0007 (7)
C3	0.0401 (12)	0.0399 (13)	0.0251 (12)	−0.0182 (10)	0.0071 (9)	−0.0077 (9)
C4	0.0728 (15)	0.0262 (10)	0.0355 (13)	−0.0161 (10)	0.0172 (11)	−0.0063 (9)
C5	0.0220 (19)	0.0167 (19)	0.043 (3)	0.0005 (17)	−0.0104 (17)	−0.0001 (16)
C6	0.0262 (16)	0.013 (9)	0.051 (2)	−0.004 (2)	−0.0130 (15)	−0.001 (2)
C7	0.033 (3)	0.027 (2)	0.078 (4)	0.001 (2)	−0.019 (2)	−0.001 (2)

O1—C5	1.447 (5)	C4—C4i	1.393 (6)
O1—C4	1.455 (3)	C4—H4	0.9500
N1—C1	1.147 (3)	C5—C6	1.487 (14)
C1—C2	1.437 (3)	C5—H5A	0.9900
C2—C3	1.385 (3)	C5—H5B	0.9900
C2—C2i	1.406 (4)	C6—C7	1.155 (16)
C3—C4	1.379 (3)	C7—H7	1.02 (6)
C3—H3	0.9500
C5—O1—C4	125.5 (3)	C3—C4—H4	119.8
N1—C1—C2	178.4 (2)	C4i—C4—H4	119.8
C3—C2—C2i	119.96 (13)	O1—C5—C6	107.3 (3)
C3—C2—C1	120.26 (18)	O1—C5—H5A	110.3
C2i—C2—C1	119.77 (10)	C6—C5—H5A	110.3
C4—C3—C2	119.6 (2)	O1—C5—H5B	110.3
C4—C3—H3	120.2	C6—C5—H5B	110.3
C2—C3—H3	120.2	H5A—C5—H5B	108.5
C3—C4—C4i	120.43 (14)	C7—C6—C5	174.6 (7)
C3—C4—O1	110.0 (2)	C6—C7—H7	178 (3)
C4i—C4—O1	129.56 (15)
C2i—C2—C3—C4	0.6 (4)	C5—O1—C4—C3	5.5 (5)
C1—C2—C3—C4	−178.2 (2)	C5—O1—C4—C4i	−173.5 (4)
C2—C3—C4—C4i	1.2 (4)	C4—O1—C5—C6	173.1 (3)
C2—C3—C4—O1	−177.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ii	0.95	2.62	3.509 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.95	2.62	3.509 (3)	155

Symmetry code: (i) .