Crystal structure of 4-(prop-2-yn-1-yl-oxy)benzo-nitrile.

In the title compound, C10H7NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yl-oxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propyn-yloxy oxygen atom. In the crystal, a hydrogen bond between the acetyl-enic C-H atom and the cyano nitro-gen atom link the mol-ecules into wave-like [30-1] C(11) chains. These chains are connected by Csp (2)-H⋯πac (πac is the acetyl-inic C-C triple bond) close contacts [2.794 (1) Å], resulting in a rolling sheet structure parallel to the ac plane and aromatic π-π stacking inter-actions between the sheets [centroid-centroid distance = 3.593 (2) Å] generate a three-dimensional network.

Related literature

The title compound is an aryl propargyl ether derivative which attracts inter­est with regard to Claisen rearrangement (Kenny et al. 2006 ▸; Wang et al. 2012 ▸) or cleavage of the O–CH2 bond by boron reagents (Yao et al. 2009 ▸). For related structures of 4-(prop-2-yn-1-yl­oxy)benzenes, see: Lindeman et al. (1993 ▸); Zhu et al. (2006 ▸); Zhang et al. (2008 ▸); Marsh (2009 ▸); Ranjith et al. (2010 ▸); Li et al. (2009 ▸); Ao et al. (2011 ▸); Al-Mehana et al. (2011 ▸); Belay et al. (2012 ▸); Doi & Okuno (2013 ▸).

Experimental

Crystal data

C10H7NO

M = 157.17

Monoclinic,

a = 6.033 (4) Å

b = 7.393 (5) Å

c = 17.527 (11) Å

β = 90.836 (11)°

V = 781.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 93 K

0.20 × 0.07 × 0.03 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: numerical (NUMABS; Rigaku, 1999 ▸) T min = 0.986, T max = 0.997

6174 measured reflections

1795 independent reflections

1457 reflections with F 2 > 2.0σ(F 2)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.120

S = 1.08

1795 reflections

113 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▸); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: CrystalStructure (Rigaku, 2014 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014028035/hb7326sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014028035/hb7326Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014028035/hb7326Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014028035/hb7326fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level and H atoms are shown as small spheres.

Click here for additional data file.

x y z x y z x y z x y z . DOI: 10.1107/S2056989014028035/hb7326fig2.tif

Part of the crystal structure showing the rolling sheet structure formed by the C–H⋯N and C–H⋯π hydrogen bonds [Symmetry codes: (i) x − , −y + , z + ; (ii) x + , −y + , z − ; (iii) x + , −y + , z − ; (iv) x − , −y + , z + ].

Click here for additional data file.

x y z x y z . DOI: 10.1107/S2056989014028035/hb7326fig3.tif

Part of the crystal structure showing the inter­sheet π⋯π stacking inter­actions and the weak C–H⋯O hydrogen bonds [Symmetry codes: (v) −x + 2, −y + 1, −z; (vi) −x + 1, −y + 1, −z].

CCDC reference: 1041123

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H7NO	F(000) = 328.00
Mr = 157.17	Dx = 1.335 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 6.033 (4) Å	Cell parameters from 2559 reflections
b = 7.393 (5) Å	θ = 2.3–31.1°
c = 17.527 (11) Å	µ = 0.09 mm−1
β = 90.836 (11)°	T = 93 K
V = 781.7 (9) Å3	Platelet, colorless
Z = 4	0.20 × 0.07 × 0.03 mm

Rigaku Saturn724+ diffractometer	1457 reflections with F2 > 2σ(F2)
Detector resolution: 28.445 pixels mm-1	Rint = 0.046
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: numerical (NUMABS; Rigaku, 1999)	h = −7→7
Tmin = 0.986, Tmax = 0.997	k = −9→9
6174 measured reflections	l = −21→22
1795 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.1471P] where P = (Fo2 + 2Fc2)/3
1795 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
O1	0.66646 (16)	0.60053 (14)	0.09599 (6)	0.0181 (3)
N1	1.4021 (2)	0.95596 (18)	−0.14609 (7)	0.0234 (3)
C1	1.1274 (2)	0.81486 (19)	−0.05087 (8)	0.0166 (3)
C2	1.1843 (2)	0.79920 (19)	0.02615 (8)	0.0175 (3)
C3	1.0358 (2)	0.72770 (19)	0.07719 (8)	0.0168 (3)
C4	0.8276 (2)	0.67109 (18)	0.05072 (8)	0.0152 (3)
C5	0.7705 (2)	0.68441 (19)	−0.02634 (8)	0.0162 (3)
C6	0.9187 (2)	0.75633 (19)	−0.07715 (8)	0.0168 (3)
C7	1.2805 (2)	0.8928 (2)	−0.10375 (8)	0.0176 (3)
C8	0.7121 (2)	0.5908 (2)	0.17643 (8)	0.0197 (3)
C9	0.5068 (2)	0.5386 (2)	0.21392 (8)	0.0190 (3)
C10	0.3416 (3)	0.4999 (2)	0.24560 (9)	0.0235 (4)
H1	0.211 (3)	0.479 (3)	0.2728 (11)	0.033 (5)*
H2	1.32622	0.838	0.04368	0.0210*
H3	1.07475	0.71712	0.12971	0.0201*
H5	0.62929	0.64389	−0.0439	0.0195*
H6	0.8798	0.76623	−0.1297	0.0202*
H8A	0.76355	0.70976	0.19566	0.0236*
H8B	0.82942	0.50026	0.18705	0.0236*

	U11	U22	U33	U12	U13	U23
O1	0.0144 (5)	0.0253 (6)	0.0147 (5)	−0.0035 (4)	0.0030 (4)	0.0018 (4)
N1	0.0173 (6)	0.0298 (7)	0.0233 (7)	0.0007 (6)	0.0032 (5)	0.0022 (6)
C1	0.0143 (7)	0.0156 (7)	0.0199 (8)	0.0023 (5)	0.0042 (6)	−0.0003 (6)
C2	0.0117 (7)	0.0177 (7)	0.0231 (8)	0.0021 (5)	0.0005 (6)	−0.0021 (6)
C3	0.0146 (7)	0.0199 (7)	0.0158 (7)	0.0018 (5)	−0.0005 (6)	0.0003 (6)
C4	0.0131 (6)	0.0141 (7)	0.0186 (7)	0.0011 (5)	0.0046 (5)	−0.0006 (6)
C5	0.0119 (7)	0.0174 (7)	0.0193 (8)	0.0003 (5)	−0.0005 (5)	−0.0007 (6)
C6	0.0160 (7)	0.0189 (7)	0.0155 (7)	0.0015 (6)	0.0004 (6)	−0.0003 (6)
C7	0.0141 (7)	0.0195 (7)	0.0193 (8)	0.0012 (6)	−0.0001 (6)	−0.0011 (6)
C8	0.0155 (7)	0.0276 (8)	0.0161 (8)	−0.0004 (6)	0.0024 (6)	0.0006 (6)
C9	0.0179 (7)	0.0239 (8)	0.0151 (7)	0.0018 (6)	−0.0002 (6)	0.0005 (6)
C10	0.0182 (7)	0.0339 (9)	0.0185 (8)	−0.0014 (7)	0.0027 (6)	0.0000 (7)

O1—C4	1.3673 (18)	C8—C9	1.463 (2)
O1—C8	1.434 (2)	C9—C10	1.183 (2)
N1—C7	1.150 (2)	C2—H2	0.950
C1—C2	1.393 (2)	C3—H3	0.950
C1—C6	1.403 (2)	C5—H5	0.950
C1—C7	1.438 (2)	C6—H6	0.950
C2—C3	1.380 (2)	C8—H8A	0.990
C3—C4	1.397 (2)	C8—H8B	0.990
C4—C5	1.392 (2)	C10—H1	0.94 (2)
C5—C6	1.378 (2)
C4—O1—C8	117.49 (11)	C1—C2—H2	119.768
C2—C1—C6	119.99 (13)	C3—C2—H2	119.770
C2—C1—C7	120.43 (13)	C2—C3—H3	120.380
C6—C1—C7	119.58 (13)	C4—C3—H3	120.387
C1—C2—C3	120.46 (13)	C4—C5—H5	119.993
C2—C3—C4	119.23 (13)	C6—C5—H5	119.976
O1—C4—C3	124.41 (13)	C1—C6—H6	120.174
O1—C4—C5	114.96 (12)	C5—C6—H6	120.181
C3—C4—C5	120.63 (13)	O1—C8—H8A	110.181
C4—C5—C6	120.03 (13)	O1—C8—H8B	110.187
C1—C6—C5	119.65 (13)	C9—C8—H8A	110.179
N1—C7—C1	179.63 (15)	C9—C8—H8B	110.175
O1—C8—C9	107.64 (12)	H8A—C8—H8B	108.478
C8—C9—C10	178.27 (16)	C9—C10—H1	175.1 (12)
C4—O1—C8—C9	171.29 (10)	C1—C2—C3—C4	0.0 (2)
C8—O1—C4—C3	2.52 (18)	C2—C3—C4—O1	−179.13 (12)
C8—O1—C4—C5	−177.34 (10)	C2—C3—C4—C5	0.7 (2)
C2—C1—C6—C5	0.4 (2)	O1—C4—C5—C6	178.94 (10)
C6—C1—C2—C3	−0.6 (2)	C3—C4—C5—C6	−0.9 (2)
C7—C1—C2—C3	178.70 (12)	C4—C5—C6—C1	0.4 (2)
C7—C1—C6—C5	−178.91 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H1···N1i	0.94 (2)	2.41 (2)	3.300 (3)	158.18 (11)
C6—H6···C10ii	0.95	2.79	3.616 (3)	145

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C10H1N1i	0.94(2)	2.41(2)	3.300(3)	158.18(11)
C6H6C10ii	0.95	2.79	3.616(3)	145

Symmetry codes: (i) ; (ii) .