3-(Prop-2-yn-1-yl-oxy)phthalo-nitrile.

In the title compound, C11H6N2O {systematic name: 3-(prop-2-yn-1-yl-oxy)benzene-1,2-dicarbo-nitrile}, the 14 non-H atoms are approximately coplanar (r.m.s. deviation = 0.051 Å) with the terminal ethyne group being syn with the adjacent cyano residue. In the crystal, centrosymmetric dimers are connected by pairs of C-H⋯N inter-actions and these are linked into a supra-molecular tape parallel to (1-30) via C-H⋯N inter-actions involving the same N atom as acceptor.

Related literature

For background to functionalized phthalocyanines, see: Chin et al. (2012 ▶). For background to the synthesis of precursor nitriles, see: Wu et al. (1998 ▶); Seven et al. (2009 ▶).

Experimental

Crystal data

C11H6N2O

M = 182.18

Monoclinic,

a = 4.014 (4) Å

b = 6.833 (7) Å

c = 33.85 (3) Å

β = 90.77 (2)°

V = 928.1 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.30 × 0.16 × 0.08 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.974, T max = 0.993

6610 measured reflections

1751 independent reflections

1310 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.250

S = 1.13

1751 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015663/hg5321sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015663/hg5321Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015663/hg5321Isup3.cml

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

C11H6N2O	F(000) = 376
Mr = 182.18	Dx = 1.304 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2684 reflections
a = 4.014 (4) Å	θ = 2.4–28.4°
b = 6.833 (7) Å	µ = 0.09 mm−1
c = 33.85 (3) Å	T = 153 K
β = 90.77 (2)°	Prism, colourless
V = 928.1 (16) Å3	0.30 × 0.16 × 0.08 mm
Z = 4

Bruker APEXII diffractometer	1751 independent reflections
Radiation source: fine-focus sealed tube	1310 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 25.7°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −4→4
Tmin = 0.974, Tmax = 0.993	k = −8→8
6610 measured reflections	l = −40→41

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.250	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.1092P)2 + 0.8456P] where P = (Fo2 + 2Fc2)/3
1751 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.1024 (7)	0.3511 (3)	0.07894 (6)	0.0506 (7)
N1	0.4013 (9)	0.7927 (4)	0.10745 (9)	0.0563 (9)
N2	0.1893 (10)	0.8135 (5)	0.21998 (10)	0.0680 (11)
C1	0.0004 (8)	0.3448 (5)	0.11659 (9)	0.0392 (8)
C2	0.0883 (8)	0.5067 (5)	0.13953 (9)	0.0385 (8)
C3	0.0045 (8)	0.5137 (5)	0.17948 (9)	0.0412 (8)
C4	−0.1691 (9)	0.3613 (6)	0.19646 (11)	0.0526 (10)
H4	−0.2270	0.3655	0.2236	0.063*
C5	−0.2565 (9)	0.2033 (6)	0.17330 (11)	0.0525 (10)
H5	−0.3765	0.0984	0.1848	0.063*
C6	−0.1754 (9)	0.1927 (5)	0.13400 (11)	0.0486 (9)
H6	−0.2392	0.0818	0.1188	0.058*
C7	0.0045 (10)	0.1952 (6)	0.05273 (10)	0.0515 (10)
H7A	−0.2412	0.1905	0.0499	0.062*
H7B	0.0831	0.0678	0.0632	0.062*
C8	0.1545 (9)	0.2349 (5)	0.01494 (10)	0.0498 (9)
C9	0.2816 (12)	0.2662 (7)	−0.01551 (12)	0.0694 (13)
H9	0.3844	0.2914	−0.0401	0.083*
C10	0.2645 (8)	0.6647 (5)	0.12159 (9)	0.0404 (8)
C11	0.1051 (9)	0.6805 (6)	0.20227 (10)	0.0495 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0697 (17)	0.0452 (14)	0.0369 (13)	−0.0151 (12)	0.0050 (11)	−0.0086 (10)
N1	0.074 (2)	0.0469 (18)	0.0487 (18)	−0.0159 (16)	0.0095 (16)	−0.0035 (14)
N2	0.088 (3)	0.073 (2)	0.0424 (18)	−0.003 (2)	0.0059 (17)	−0.0152 (17)
C1	0.0385 (18)	0.0380 (17)	0.0410 (17)	−0.0019 (13)	−0.0001 (13)	0.0016 (13)
C2	0.0385 (17)	0.0362 (17)	0.0408 (17)	0.0010 (13)	0.0019 (13)	0.0024 (13)
C3	0.0407 (18)	0.0452 (19)	0.0376 (16)	0.0053 (15)	0.0020 (13)	0.0023 (14)
C4	0.053 (2)	0.063 (2)	0.0417 (18)	0.0042 (18)	0.0083 (16)	0.0119 (17)
C5	0.047 (2)	0.051 (2)	0.060 (2)	−0.0061 (17)	0.0055 (17)	0.0173 (18)
C6	0.048 (2)	0.0408 (19)	0.056 (2)	−0.0084 (15)	−0.0022 (16)	0.0037 (15)
C7	0.056 (2)	0.054 (2)	0.0438 (19)	−0.0129 (17)	−0.0041 (16)	−0.0145 (16)
C8	0.057 (2)	0.048 (2)	0.044 (2)	0.0008 (17)	−0.0083 (17)	−0.0126 (16)
C9	0.091 (3)	0.074 (3)	0.043 (2)	0.003 (2)	0.009 (2)	−0.009 (2)
C10	0.049 (2)	0.0364 (17)	0.0353 (17)	−0.0029 (15)	0.0020 (14)	−0.0048 (13)
C11	0.057 (2)	0.061 (2)	0.0313 (17)	0.0009 (18)	0.0076 (15)	−0.0044 (16)

O1—C1	1.345 (4)	C4—C5	1.377 (6)
O1—C7	1.437 (4)	C4—H4	0.9500
N1—C10	1.141 (4)	C5—C6	1.376 (5)
N2—C11	1.137 (5)	C5—H5	0.9500
C1—C6	1.391 (5)	C6—H6	0.9500
C1—C2	1.394 (5)	C7—C8	1.447 (5)
C2—C3	1.399 (5)	C7—H7A	0.9900
C2—C10	1.431 (4)	C7—H7B	0.9900
C3—C4	1.382 (5)	C8—C9	1.176 (5)
C3—C11	1.431 (5)	C9—H9	0.9500
C1—O1—C7	118.5 (3)	C4—C5—H5	119.0
O1—C1—C6	126.0 (3)	C5—C6—C1	119.9 (3)
O1—C1—C2	115.1 (3)	C5—C6—H6	120.1
C6—C1—C2	118.9 (3)	C1—C6—H6	120.1
C1—C2—C3	120.2 (3)	O1—C7—C8	107.0 (3)
C1—C2—C10	119.0 (3)	O1—C7—H7A	110.3
C3—C2—C10	120.7 (3)	C8—C7—H7A	110.3
C4—C3—C2	120.3 (3)	O1—C7—H7B	110.3
C4—C3—C11	121.1 (3)	C8—C7—H7B	110.3
C2—C3—C11	118.6 (3)	H7A—C7—H7B	108.6
C5—C4—C3	118.7 (3)	C9—C8—C7	178.9 (4)
C5—C4—H4	120.7	C8—C9—H9	180.0
C3—C4—H4	120.7	N1—C10—C2	179.0 (4)
C6—C5—C4	122.0 (3)	N2—C11—C3	178.9 (4)
C6—C5—H5	119.0
C7—O1—C1—C6	4.8 (5)	C11—C3—C4—C5	−179.3 (3)
C7—O1—C1—C2	−176.3 (3)	C3—C4—C5—C6	0.2 (6)
O1—C1—C2—C3	−178.1 (3)	C4—C5—C6—C1	0.0 (6)
C6—C1—C2—C3	0.9 (5)	O1—C1—C6—C5	178.2 (3)
O1—C1—C2—C10	2.0 (4)	C2—C1—C6—C5	−0.6 (5)
C6—C1—C2—C10	−179.0 (3)	C1—O1—C7—C8	−178.3 (3)
C1—C2—C3—C4	−0.7 (5)	O1—C7—C8—C9	74 (21)
C10—C2—C3—C4	179.2 (3)	C1—C2—C10—N1	123 (21)
C1—C2—C3—C11	178.7 (3)	C3—C2—C10—N1	−57 (21)
C10—C2—C3—C11	−1.4 (5)	C4—C3—C11—N2	153 (24)
C2—C3—C4—C5	0.1 (5)	C2—C3—C11—N2	−26 (25)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1i	0.95	2.47	3.335 (6)	151
C9—H9···N1ii	0.95	2.51	3.402 (6)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N1i	0.95	2.47	3.335 (6)	151
C9—H9⋯N1ii	0.95	2.51	3.402 (6)	156

Symmetry codes: (i) ; (ii) .