4-(Dodec-yloxy)benzonitrile.

In the title compound, C(19)H(29)NO, the C-C and C-N bond distances of the benzonitrile group are 1.445 (2) and 1.157 (2) Å, respectively. The aliphatic fragment adopts a bent zigzag arangement which differs from the planar zigzag arrangement normally observed in n-alkanes or long-chain alkyl-benzenes. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds occur. A C-H⋯N inter-action also occurs. In the crystal, mol-ecules are packed with the nitrile and aliphatic groups oriented in a head-to-tail fashion involving, forming a ripple-like motif along the a axis.

Related literature

For standard bond lengths, see Allen et al. (1987 ▶). For related structures, see: Merz (2002 ▶); Britton et al. (2004 ▶); Kwong et al. (2011 ▶); Boese et al. (1999 ▶). The title compound was synthesised by reacting hy­droxy­benzonitrile with bromo­alkane, see Rahman et al. (2009 ▶).

Experimental

Crystal data

C19H29NO

M = 287.45

Monoclinic,

a = 5.7080 (6) Å

b = 7.3644 (8) Å

c = 40.642 (5) Å

β = 90°

V = 1708.4 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.52 mm−1

T = 100 K

0.17 × 0.14 × 0.09 mm

Data collection

Oxford Diffraction Gemini E diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.930, T max = 0.955

9444 measured reflections

3214 independent reflections

2575 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 0.98

3202 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.25 e Å−3

Data collection: Gemini (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041602/kp2353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041602/kp2353Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041602/kp2353Isup3.cml

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

C19H29NO	F(000) = 632
Mr = 287.45	Dx = 1.117 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
a = 5.7080 (6) Å	Cell parameters from 3853 reflections
b = 7.3644 (8) Å	θ = 3–71°
c = 40.642 (5) Å	µ = 0.52 mm−1
β = 90°	T = 100 K
V = 1708.4 (3) Å3	Plate-like, colourless
Z = 4	0.17 × 0.14 × 0.09 mm

Oxford Diffraction Gemini E diffractometer	3214 independent reflections
Radiation source: sealed x-ray tube	2575 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω/2θ scans	θmax = 71.6°, θmin = 4.4°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −6→6
Tmin = 0.930, Tmax = 0.955	k = −8→9
9444 measured reflections	l = −37→49

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.127	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.05P)2 + 1.35P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.98	(Δ/σ)max = 0.007
3202 reflections	Δρmax = 0.24 e Å−3
190 parameters	Δρmin = −0.25 e Å−3
0 restraints

Refinement. Refinement. For this compound, 9444 numbers of reflections were collected and measured during the refinement. Symmetry related reflections were measured more than once and after merging the symmetry equivalent reflections there were only 3214 reflection left. 12 more reflections were filtered, as σ cutoff was set as 3 and (sin?/x)set to>0.01 (to eliminate reflection measured near the vicinity of beam stop) therefore numbers of reflection reduced to 3202.

	x	y	z	Uiso*/Ueq
O1	0.33735 (19)	0.61108 (16)	0.45325 (3)	0.0243
C2	0.1734 (3)	0.6793 (2)	0.47454 (4)	0.0214
C3	0.2277 (3)	0.6631 (2)	0.50786 (4)	0.0221
C4	0.0719 (3)	0.7247 (2)	0.53150 (4)	0.0228
C5	−0.1403 (3)	0.8033 (2)	0.52206 (4)	0.0219
C6	−0.3025 (3)	0.8685 (2)	0.54668 (4)	0.0234
N7	−0.4333 (3)	0.9209 (2)	0.56623 (4)	0.0295
C8	−0.1922 (3)	0.8209 (2)	0.48877 (4)	0.0221
C9	−0.0351 (3)	0.7606 (2)	0.46502 (4)	0.0220
C10	0.2944 (3)	0.6284 (2)	0.41859 (4)	0.0242
C11	0.5019 (3)	0.5506 (2)	0.40024 (4)	0.0252
C12	0.4902 (3)	0.5918 (2)	0.36351 (4)	0.0246
C13	0.6978 (3)	0.5162 (2)	0.34403 (4)	0.0257
C14	0.7033 (3)	0.5790 (2)	0.30831 (4)	0.0251
C15	0.9124 (3)	0.5066 (2)	0.28868 (4)	0.0258
C16	0.9230 (3)	0.5776 (2)	0.25349 (4)	0.0257
C17	1.1323 (3)	0.5068 (2)	0.23378 (4)	0.0257
C18	1.1450 (3)	0.5806 (2)	0.19882 (4)	0.0258
C19	1.3543 (3)	0.5106 (2)	0.17902 (4)	0.0259
C20	1.3684 (3)	0.5847 (3)	0.14407 (4)	0.0282
C21	1.5784 (3)	0.5133 (3)	0.12487 (4)	0.0322
H31	0.3704	0.6093	0.5144	0.0260*
H41	0.1098	0.7150	0.5546	0.0259*
H81	−0.3353	0.8725	0.4821	0.0251*
H91	−0.0710	0.7743	0.4422	0.0250*
H102	0.2751	0.7577	0.4131	0.0287*
H101	0.1498	0.5632	0.4128	0.0284*
H111	0.6426	0.6050	0.4091	0.0296*
H112	0.5060	0.4186	0.4040	0.0302*
H122	0.4875	0.7226	0.3605	0.0291*
H121	0.3473	0.5416	0.3544	0.0290*
H131	0.8392	0.5561	0.3546	0.0305*
H132	0.6919	0.3834	0.3445	0.0313*
H142	0.7085	0.7111	0.3080	0.0303*
H141	0.5615	0.5402	0.2974	0.0293*
H151	1.0537	0.5428	0.3000	0.0304*
H152	0.9037	0.3730	0.2881	0.0309*
H162	0.9305	0.7093	0.2541	0.0313*
H161	0.7809	0.5426	0.2420	0.0302*
H172	1.2745	0.5408	0.2450	0.0312*
H171	1.1235	0.3737	0.2328	0.0314*
H181	1.1543	0.7134	0.1998	0.0308*
H182	1.0027	0.5487	0.1872	0.0310*
H192	1.4972	0.5440	0.1907	0.0307*
H191	1.3442	0.3777	0.1780	0.0315*
H201	1.3788	0.7175	0.1451	0.0338*
H202	1.2254	0.5535	0.1326	0.0335*
H212	1.5813	0.5587	0.1021	0.0465*
H211	1.7246	0.5486	0.1352	0.0467*
H213	1.5746	0.3804	0.1239	0.0474*

	U11	U22	U33	U12	U13	U23
O1	0.0228 (6)	0.0292 (7)	0.0208 (6)	0.0029 (5)	−0.0019 (5)	−0.0005 (5)
C2	0.0216 (8)	0.0179 (8)	0.0247 (8)	−0.0037 (7)	−0.0010 (6)	−0.0006 (7)
C3	0.0195 (8)	0.0198 (8)	0.0269 (9)	−0.0008 (7)	−0.0045 (6)	0.0010 (7)
C4	0.0238 (9)	0.0212 (9)	0.0235 (8)	−0.0035 (7)	−0.0044 (7)	0.0001 (7)
C5	0.0208 (8)	0.0199 (8)	0.0251 (8)	−0.0043 (7)	0.0002 (6)	0.0002 (7)
C6	0.0224 (9)	0.0215 (8)	0.0261 (9)	−0.0022 (7)	−0.0055 (7)	0.0019 (7)
N7	0.0269 (8)	0.0338 (9)	0.0279 (8)	0.0001 (7)	−0.0017 (6)	−0.0015 (7)
C8	0.0173 (8)	0.0207 (9)	0.0283 (9)	−0.0022 (6)	−0.0044 (6)	0.0016 (7)
C9	0.0223 (8)	0.0211 (9)	0.0224 (8)	−0.0037 (7)	−0.0039 (6)	0.0016 (6)
C10	0.0231 (9)	0.0274 (9)	0.0221 (8)	−0.0011 (7)	−0.0031 (7)	0.0000 (7)
C11	0.0227 (9)	0.0283 (9)	0.0247 (9)	0.0004 (7)	−0.0018 (7)	−0.0009 (7)
C12	0.0226 (8)	0.0264 (9)	0.0249 (9)	−0.0001 (7)	−0.0024 (7)	0.0007 (7)
C13	0.0257 (9)	0.0274 (9)	0.0240 (9)	0.0034 (7)	−0.0025 (7)	−0.0012 (7)
C14	0.0228 (9)	0.0282 (9)	0.0244 (9)	0.0010 (7)	−0.0026 (7)	−0.0001 (7)
C15	0.0249 (9)	0.0277 (9)	0.0249 (9)	0.0026 (7)	−0.0036 (7)	−0.0016 (7)
C16	0.0251 (9)	0.0277 (9)	0.0242 (9)	0.0011 (7)	−0.0032 (7)	0.0001 (7)
C17	0.0254 (9)	0.0283 (9)	0.0234 (9)	0.0010 (7)	−0.0041 (7)	−0.0013 (7)
C18	0.0239 (9)	0.0284 (9)	0.0251 (9)	0.0009 (7)	−0.0034 (7)	0.0008 (7)
C19	0.0255 (9)	0.0281 (9)	0.0240 (9)	0.0003 (7)	−0.0040 (7)	−0.0016 (7)
C20	0.0270 (9)	0.0313 (10)	0.0264 (9)	0.0000 (8)	−0.0026 (7)	0.0006 (7)
C21	0.0308 (10)	0.0387 (11)	0.0269 (9)	−0.0008 (8)	−0.0012 (8)	−0.0007 (8)

O1—C2	1.3698 (19)	C13—H132	0.979
O1—C10	1.4355 (19)	C14—C15	1.531 (2)
C2—C3	1.394 (2)	C14—H142	0.973
C2—C9	1.387 (2)	C14—H141	0.966
C3—C4	1.385 (2)	C15—C16	1.524 (2)
C3—H31	0.943	C15—H151	0.967
C4—C5	1.396 (2)	C15—H152	0.985
C4—H41	0.965	C16—C17	1.530 (2)
C5—C6	1.445 (2)	C16—H162	0.972
C5—C8	1.391 (2)	C16—H161	0.970
C6—N7	1.157 (2)	C17—C18	1.523 (2)
C8—C9	1.390 (2)	C17—H172	0.963
C8—H81	0.941	C17—H171	0.982
C9—H91	0.954	C18—C19	1.530 (2)
C10—C11	1.512 (2)	C18—H181	0.980
C10—H102	0.984	C18—H182	0.968
C10—H101	0.984	C19—C20	1.524 (2)
C11—C12	1.525 (2)	C19—H192	0.976
C11—H111	0.967	C19—H191	0.981
C11—H112	0.984	C20—C21	1.524 (2)
C12—C13	1.530 (2)	C20—H201	0.981
C12—H122	0.971	C20—H202	0.967
C12—H121	0.969	C21—H212	0.985
C13—C14	1.524 (2)	C21—H211	0.969
C13—H131	0.961	C21—H213	0.980
C2—O1—C10	118.08 (12)	C15—C14—H142	108.6
O1—C2—C3	115.50 (14)	C13—C14—H141	109.3
O1—C2—C9	124.62 (14)	C15—C14—H141	108.1
C3—C2—C9	119.89 (15)	H142—C14—H141	108.4
C2—C3—C4	120.20 (15)	C14—C15—C16	113.61 (14)
C2—C3—H31	120.0	C14—C15—H151	107.8
C4—C3—H31	119.8	C16—C15—H151	108.7
C3—C4—C5	120.14 (15)	C14—C15—H152	108.7
C3—C4—H41	120.4	C16—C15—H152	108.8
C5—C4—H41	119.4	H151—C15—H152	109.2
C4—C5—C6	120.23 (15)	C15—C16—C17	113.93 (14)
C4—C5—C8	119.37 (15)	C15—C16—H162	108.6
C6—C5—C8	120.40 (15)	C17—C16—H162	108.6
C5—C6—N7	179.56 (17)	C15—C16—H161	109.0
C5—C8—C9	120.54 (15)	C17—C16—H161	108.1
C5—C8—H81	120.1	H162—C16—H161	108.3
C9—C8—H81	119.4	C16—C17—C18	113.81 (14)
C8—C9—C2	119.85 (15)	C16—C17—H172	108.8
C8—C9—H91	120.1	C18—C17—H172	107.9
C2—C9—H91	120.0	C16—C17—H171	108.7
O1—C10—C11	108.46 (13)	C18—C17—H171	108.8
O1—C10—H102	109.2	H172—C17—H171	108.7
C11—C10—H102	110.0	C17—C18—C19	114.02 (14)
O1—C10—H101	109.5	C17—C18—H181	108.6
C11—C10—H101	110.8	C19—C18—H181	108.4
H102—C10—H101	108.9	C17—C18—H182	109.1
C10—C11—C12	111.90 (14)	C19—C18—H182	108.5
C10—C11—H111	108.0	H181—C18—H182	108.0
C12—C11—H111	108.6	C18—C19—C20	114.25 (14)
C10—C11—H112	108.4	C18—C19—H192	108.1
C12—C11—H112	110.4	C20—C19—H192	108.7
H111—C11—H112	109.4	C18—C19—H191	108.2
C11—C12—C13	113.60 (14)	C20—C19—H191	108.8
C11—C12—H122	108.7	H192—C19—H191	108.7
C13—C12—H122	108.0	C19—C20—C21	113.30 (15)
C11—C12—H121	109.5	C19—C20—H201	108.7
C13—C12—H121	108.5	C21—C20—H201	108.5
H122—C12—H121	108.5	C19—C20—H202	108.7
C12—C13—C14	113.50 (14)	C21—C20—H202	109.5
C12—C13—H131	107.9	H201—C20—H202	108.0
C14—C13—H131	108.5	C20—C21—H212	112.2
C12—C13—H132	109.1	C20—C21—H211	111.4
C14—C13—H132	108.8	H212—C21—H211	107.5
H131—C13—H132	109.0	C20—C21—H213	110.4
C13—C14—C15	114.01 (14)	H212—C21—H213	107.5
C13—C14—H142	108.3	H211—C21—H213	107.7

D—H···A	D—H	H···A	D···A	D—H···A
C10—H102···N7i	0.98	2.67	3.468 (2)	139.
C3—H31···O1ii	0.94	2.67	3.569 (5)	159.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H102⋯N7i	0.98	2.67	3.468 (2)	139
C3—H31⋯O1ii	0.94	2.67	3.569 (5)	159

Symmetry codes: (i) ; (ii) .