Crystal structure of 4-(prop-2-yn-1-yl­oxy)benzo­nitrile

Kanagawa, M.; Okuno, T.

doi:10.1107/S2056989014028035

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o97-o98

doi:10.1107/S2056989014028035

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Crystal structure of 4-(prop-2-yn-1-yloxy)benzonitrile

Mayu Kanagawa ^a and Tsunehisa Okuno ^a ^*

^aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
^*Correspondence e-mail: okuno@center.wakayama-u.ac.jp

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 22 November 2014; accepted 24 December 2014; online 10 January 2015)

In the title compound, C₁₀H₇NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yloxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propynyloxy oxygen atom. In the crystal, a hydrogen bond between the acetylenic C—H atom and the cyano nitrogen atom link the molecules into wave-like [30-1] C(11) chains. These chains are connected by Csp²—H⋯π_ac (π_ac is the acetylinic 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 interactions between the sheets [centroid–centroid distance = 3.593 (2) Å] generate a three-dimensional network.

Keywords: crystal structure; prop-2-yn-1-yloxy; hydrogen bonding; C—H⋯π interactions; π–π stacking interactions.

CCDC reference: 1041123

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₀H₇NO
M_r = 157.17
Monoclinic, P 2₁ /n
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

2.2. 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 F² > 2.0σ(F²)
R_int = 0.046

2.3. Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.120
S = 1.08
1795 reflections
113 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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
Symmetry codes: (i) $[x-{\script{3\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 1041123

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989014028035/hb7326sup1.cif

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

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

checkCIF report

Comment top

The title compound, C₁₀H₇N₁O₁, is an aryl propargyl ether derivative which attracts interest from viewpoints of Claisen rearrangement (Kenny et al. 2006; Wang et al. 2012) or cleavage of O–CH₂ bond by boron reagents (Yao et al. 2009). In these reactions, a direction of the lone pair of the oxygen has large influence upon reactivity.

The molecule has an almost planar structure (atoms C1—C10/N1/O1 are essentailly co-planar with r.m.s. deviation = 0.0862 Å), indicating an effective conjugation of the cyano group, the C1—C6 benzene ring and the lone pair of the O1 (Fig. 1). This is presumably because push-pull effect between an electron donating alkyloxy group and an electron withdrawing cyano group (Zhu et al. 2006; Marsh 2009; Ranjith et al. 2010; Ao et al. 2011; Al-Mehana et al. 2011; Belay et al. 2012; Doi & Okuno 2013).

In the crystal, C10–H1···N1ⁱ hydrogen bonds [Symmetry code: (i) x - 3/2, -y + 3/2, z + 1/2] connect the molecules to make a one-dimensional wavy chain. Intermolecular C6–H6···C10ⁱⁱ interaction [Symmetry code: (ii) x + 1/2, -y + 3/2, z - 1/2], whose distance is 2.794 (1) Å, binds the chains to form a rolling sheet structure as shown in Fig. 2.

Fig. 3 shows π···π stacking interactions between the sheets, where the centroid to centroid distance is 3.593 (2) Å and the C3···C5^v is 3.387 (3) Å [Symmetry code: (v) -x + 2, -y + 1, -z]. The molecules also form weak intersheet C5–H5···O1^vi bonds whose distance is 2.690 (1) Å [Symmetry code: (vi) -x + 1, -y + 1, -z]. In this crystal, the intermolecular hydrogen bonds, the C–H···π interactions and the π···π stacking interactions are found to make a three-dimensional molecular network.

Related literature top

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 top

The title compound is commercially available. Colourless platelets of sufficient quality for diffraction measurements were prepared by sublimation at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level and H atoms are shown as small spheres.
	Fig. 2. 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 - 3/2, -y + 3/2, z + 1/2; (ii) x + 1/2, -y + 3/2, z - 1/2; (iii) x + 3/2, -y + 3/2, z - 1/2; (iv) x - 1/2, -y + 3/2, z + 1/2].
	Fig. 3. 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].

4-(Prop-2-yn-1-yloxy)benzonitrile top

Crystal data top

C₁₀H₇NO	F(000) = 328.00
M_r = 157.17	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0584P)² + 0.1471P] where P = (F_o² + 2F_c²)/3
1795 reflections	(Δ/σ)_max < 0.001
113 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₀H₇NO	V = 781.7 (9) Å³
M_r = 157.17	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.033 (4) Å	µ = 0.09 mm⁻¹
b = 7.393 (5) Å	T = 93 K
c = 17.527 (11) Å	0.20 × 0.07 × 0.03 mm
β = 90.836 (11)°

Data collection top

Rigaku Saturn724+ diffractometer	1795 independent reflections
Absorption correction: numerical (NUMABS; Rigaku, 1999)	1457 reflections with F² > 2σ(F²)
T_min = 0.986, T_max = 0.997	R_int = 0.046
6174 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.22 e Å⁻³
1795 reflections	Δρ_min = −0.19 e Å⁻³
113 parameters

Special details top

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−3/2, −y+3/2, z+1/2; (ii) x+1/2, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−3/2, −y+3/2, z+1/2; (ii) x+1/2, −y+3/2, z−1/2.

Acknowledgements

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

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