4-Hexyl-oxybenzamide.

In the title compound, C(13)H(19)NO(2), the dihedral angle between the benzene ring and the plane throught the non-H atoms of the amide group is 29.3 (1)°. The benzene ring and the alkane carbon skeleton plane are twisted slightly with respect to each other [5.40 (5)°]. In the crystal, mol-ecules are oriented with the amide groups head-to-head, forming N-H⋯O hydrogen-bonded dimers. The dimers are connected by further N-H⋯O hydrogen bonds into a ladder-like motif along the b axis.

Related literature

For standard bond lengths, see Allen et al. (1987 ▶). For related structures, see: Merz (2002 ▶); Jones et al. (2002 ▶); Pagola & Stephens (2009 ▶); Boese et al. (1999 ▶). For related experiments on the hydrolysis of nitrites, see: Gallardo & Begnini (1995 ▶); Pala Wilgus et al. (1995 ▶).

Experimental

Crystal data

C13H19NO2

M = 221.30

Monoclinic,

a = 12.5507 (2) Å

b = 5.16441 (9) Å

c = 18.9322 (3) Å

β = 91.4702 (16)°

V = 1226.72 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.64 mm−1

T = 150 K

0.31 × 0.08 × 0.05 mm

Data collection

Oxford Diffraction Gemini E diffractometer

Absorption correction: multi-scan (CrysAlis PRO: Oxford Diffraction, 2006 ▶) T min = 0.894, T max = 1.000

13258 measured reflections

2355 independent reflections

2165 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.01

2101 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (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 datablocks global, I. DOI: 10.1107/S1600536811003096/kp2300sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003096/kp2300Isup2.hkl

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

C13H19NO2	F(000) = 480
Mr = 221.30	Dx = 1.198 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 8720 reflections
a = 12.5507 (2) Å	θ = 3.5–70.8°
b = 5.16441 (9) Å	µ = 0.64 mm−1
c = 18.9322 (3) Å	T = 150 K
β = 91.4702 (16)°	Needle-like, colourless
V = 1226.72 (4) Å3	0.31 × 0.08 × 0.05 mm
Z = 4

Oxford Diffraction Gemini E diffractometer	2355 independent reflections
Radiation source: sealed x-ray tube	2165 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω/2θ scans	θmax = 71.0°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO: Oxford Diffraction, 2006)	h = −15→13
Tmin = 0.894, Tmax = 1.000	k = −6→6
13258 measured reflections	l = −21→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.095	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.05P)2 + 0.41P], where P = [max(Fo2,0) + 2Fc2]/3
S = 1.01	(Δ/σ)max = 0.0002608
2101 reflections	Δρmax = 0.18 e Å−3
145 parameters	Δρmin = −0.18 e Å−3
0 restraints

Refinement. For this compound, 13258 reflections were measured and collected during the refinement. However after merging the symmetry equivalent reflections, there were only 2355 independent reflections. Further 254 more reflections were filtered, as sigma cutoff was set at 3.0 and (sin theta x 2)set to >0.01 (to eliminate reflection measured near the vicinity of beam stop) therefore reduced the number of reflection to 2101 which were used in the Refinement.

	x	y	z	Uiso*/Ueq
O1	0.50007 (7)	0.75339 (18)	0.27977 (5)	0.0339
C2	0.40797 (9)	0.7236 (2)	0.31525 (6)	0.0276
C3	0.40594 (10)	0.5166 (2)	0.36254 (7)	0.0327
C4	0.31610 (10)	0.4686 (2)	0.40089 (6)	0.0302
C5	0.22742 (9)	0.6304 (2)	0.39492 (6)	0.0258
C6	0.23026 (10)	0.8374 (2)	0.34797 (6)	0.0283
C7	0.31893 (10)	0.8824 (2)	0.30718 (6)	0.0292
C8	0.13215 (9)	0.5718 (2)	0.43773 (6)	0.0265
O9	0.11152 (7)	0.34604 (16)	0.45547 (5)	0.0322
N10	0.07033 (9)	0.7708 (2)	0.45501 (6)	0.0326
C11	0.50247 (10)	0.9496 (3)	0.22591 (7)	0.0334
C12	0.61157 (10)	0.9498 (2)	0.19414 (7)	0.0337
C13	0.64375 (10)	0.6928 (2)	0.16146 (7)	0.0321
C14	0.74928 (10)	0.7091 (2)	0.12345 (7)	0.0314
C15	0.78664 (10)	0.4500 (3)	0.09497 (7)	0.0339
C16	0.89010 (11)	0.4699 (3)	0.05528 (7)	0.0392
H31	0.4688	0.4087	0.3672	0.0424*
H41	0.3139	0.3171	0.4318	0.0397*
H61	0.1691	0.9533	0.3429	0.0368*
H71	0.3177	1.0309	0.2744	0.0385*
H112	0.4882	1.1252	0.2475	0.0433*
H111	0.4461	0.9082	0.1885	0.0424*
H122	0.6652	1.0029	0.2319	0.0438*
H121	0.6111	1.0874	0.1576	0.0426*
H131	0.6479	0.5555	0.1986	0.0402*
H132	0.5859	0.6413	0.1263	0.0417*
H141	0.8049	0.7782	0.1575	0.0417*
H142	0.7433	0.8391	0.0847	0.0407*
H151	0.7949	0.3232	0.1343	0.0435*
H152	0.7299	0.3781	0.0628	0.0445*
H162	0.9124	0.2983	0.0389	0.0627*
H163	0.9472	0.5385	0.0870	0.0619*
H161	0.8823	0.5875	0.0142	0.0630*
H101	0.0938	0.9339	0.4498	0.0433*
H102	0.0124	0.7437	0.4808	0.0432*

	U11	U22	U33	U12	U13	U23
O1	0.0292 (4)	0.0377 (5)	0.0350 (5)	0.0032 (4)	0.0051 (4)	0.0078 (4)
C2	0.0281 (6)	0.0268 (6)	0.0279 (6)	−0.0015 (5)	0.0011 (4)	−0.0021 (5)
C3	0.0319 (6)	0.0296 (6)	0.0365 (7)	0.0059 (5)	0.0000 (5)	0.0042 (5)
C4	0.0367 (7)	0.0238 (6)	0.0300 (6)	0.0010 (5)	0.0007 (5)	0.0046 (5)
C5	0.0312 (6)	0.0199 (5)	0.0264 (5)	−0.0024 (4)	0.0004 (4)	−0.0026 (4)
C6	0.0317 (6)	0.0209 (6)	0.0325 (6)	0.0024 (5)	0.0019 (5)	0.0006 (5)
C7	0.0346 (6)	0.0220 (6)	0.0311 (6)	−0.0002 (5)	0.0029 (5)	0.0039 (5)
C8	0.0331 (6)	0.0216 (6)	0.0248 (5)	−0.0019 (5)	0.0001 (5)	−0.0006 (4)
O9	0.0390 (5)	0.0201 (4)	0.0378 (5)	−0.0009 (3)	0.0095 (4)	0.0028 (3)
N10	0.0382 (6)	0.0204 (5)	0.0399 (6)	−0.0006 (4)	0.0136 (5)	0.0011 (4)
C11	0.0356 (7)	0.0278 (6)	0.0373 (7)	0.0011 (5)	0.0070 (5)	0.0042 (5)
C12	0.0353 (7)	0.0279 (6)	0.0382 (7)	−0.0037 (5)	0.0071 (5)	0.0001 (5)
C13	0.0316 (6)	0.0277 (6)	0.0370 (7)	−0.0031 (5)	0.0030 (5)	−0.0013 (5)
C14	0.0335 (6)	0.0271 (6)	0.0335 (6)	−0.0027 (5)	0.0024 (5)	−0.0002 (5)
C15	0.0335 (7)	0.0292 (7)	0.0391 (7)	−0.0018 (5)	0.0013 (5)	−0.0039 (5)
C16	0.0368 (7)	0.0393 (8)	0.0415 (7)	0.0014 (6)	0.0031 (6)	−0.0071 (6)

O1—C2	1.3605 (14)	C11—H112	1.013
O1—C11	1.4384 (15)	C11—H111	1.011
C2—C3	1.3954 (17)	C12—C13	1.5233 (17)
C2—C7	1.3915 (17)	C12—H122	1.007
C3—C4	1.3792 (17)	C12—H121	0.992
C3—H31	0.968	C13—C14	1.5258 (17)
C4—C5	1.3943 (17)	C13—H131	0.998
C4—H41	0.978	C13—H132	1.007
C5—C6	1.3912 (16)	C14—C15	1.5216 (17)
C5—C8	1.4926 (16)	C14—H141	1.003
C6—C7	1.3904 (17)	C14—H142	0.996
C6—H61	0.976	C15—C16	1.5203 (18)
C7—H71	0.986	C15—H151	0.995
C8—O9	1.2423 (14)	C15—H152	0.997
C8—N10	1.3338 (15)	C16—H162	0.982
N10—H101	0.898	C16—H163	0.989
N10—H102	0.898	C16—H161	0.990
C11—C12	1.5096 (17)
C2—O1—C11	117.58 (9)	C11—C12—C13	114.45 (10)
O1—C2—C3	115.66 (11)	C11—C12—H122	108.3
O1—C2—C7	124.71 (11)	C13—C12—H122	110.2
C3—C2—C7	119.63 (11)	C11—C12—H121	106.8
C2—C3—C4	120.28 (11)	C13—C12—H121	109.7
C2—C3—H31	118.1	H122—C12—H121	106.9
C4—C3—H31	121.6	C12—C13—C14	112.69 (10)
C3—C4—C5	120.75 (11)	C12—C13—H131	110.0
C3—C4—H41	119.7	C14—C13—H131	110.0
C5—C4—H41	119.5	C12—C13—H132	107.7
C4—C5—C6	118.62 (11)	C14—C13—H132	108.8
C4—C5—C8	118.89 (10)	H131—C13—H132	107.5
C6—C5—C8	122.47 (11)	C13—C14—C15	113.43 (10)
C5—C6—C7	121.16 (11)	C13—C14—H141	108.4
C5—C6—H61	120.1	C15—C14—H141	109.0
C7—C6—H61	118.8	C13—C14—H142	109.6
C2—C7—C6	119.50 (11)	C15—C14—H142	110.5
C2—C7—H71	121.8	H141—C14—H142	105.7
C6—C7—H71	118.6	C14—C15—C16	112.97 (11)
C5—C8—O9	120.85 (10)	C14—C15—H151	109.9
C5—C8—N10	117.12 (10)	C16—C15—H151	109.9
O9—C8—N10	122.03 (11)	C14—C15—H152	108.8
C8—N10—H101	120.1	C16—C15—H152	109.2
C8—N10—H102	119.9	H151—C15—H152	105.8
H101—N10—H102	118.5	C15—C16—H162	110.4
O1—C11—C12	108.58 (10)	C15—C16—H163	109.8
O1—C11—H112	109.7	H162—C16—H163	107.9
C12—C11—H112	109.4	C15—C16—H161	111.2
O1—C11—H111	108.7	H162—C16—H161	109.2
C12—C11—H111	110.3	H163—C16—H161	108.3
H112—C11—H111	110.1

D—H···A	D—H	H···A	D···A	D—H···A
N10—H101···O9i	0.90	2.14	3.0153 (18)	164
N10—H102···O9ii	0.90	2.04	2.9401 (18)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H101⋯O9i	0.90	2.14	3.0153 (18)	164
N10—H102⋯O9ii	0.90	2.04	2.9401 (18)	174

Symmetry codes: (i) ; (ii) .