2-Butyl-5-pentyl-benzene-1,3-diol.

In the title compound, C(15)H(24)O(2), a natural dialkyl-resorcinol commonly named stemphol, the mol-ecules are linked into C(6) and C(2) (2)(4) chains and R(4) (4)(16) rings by inter-molecular O-H⋯O hydrogen bonds, creating mol-ecular sheets parallel to the (010) plane. The alkyl chains are directed orthogonally away from these planes in almost complete extension.

Related literature

For general background, synthesis, biological activity and related structures, see: Achenbach & Kohl (1979 ▶); Andersen & Frisvad (2004 ▶); Marumo et al. (1985 ▶); Solfrizzo et al. (1994 ▶); Stodola et al. (1973 ▶). For structural discussion, see: Etter (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H24O2

M = 236.34

Monoclinic,

a = 4.654 (2) Å

b = 25.450 (5) Å

c = 12.790 (4) Å

β = 108.12 (1)°

V = 1439.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.50 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.881, T max = 0.994

15852 measured reflections

2631 independent reflections

1703 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.131

S = 1.04

2631 reflections

158 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT (Nonius, 1999 ▶); cell refinement: DENZO; data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and CrystalBuilder (Welter, 2006 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018820/dn2455sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018820/dn2455Isup2.hkl

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

C15H24O2	F(000) = 520
Mr = 236.34	Dx = 1.090 Mg m−3
Monoclinic, P21/c	Melting point: 364 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 4.654 (2) Å	Cell parameters from 2700 reflections
b = 25.450 (5) Å	θ = 0.4–25.4°
c = 12.790 (4) Å	µ = 0.07 mm−1
β = 108.12 (1)°	T = 293 K
V = 1439.8 (8) Å3	Needle, colourless
Z = 4	0.50 × 0.10 × 0.08 mm

Nonius KappaCCD diffractometer	2631 independent reflections
Radiation source: fine-focus sealed tube	1703 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.3°, θmin = 2.3°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −5→5
Tmin = 0.881, Tmax = 0.994	k = −30→30
15852 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.1805P] where P = (Fo2 + 2Fc2)/3
2631 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.0951 (3)	0.27129 (5)	0.28490 (10)	0.0555 (4)
H1	0.2648	0.2719	0.3299	0.083*
O2	−0.2986 (2)	0.22721 (5)	−0.09324 (9)	0.0517 (4)
H2	−0.2074	0.2253	−0.1386	0.077*
C1	−0.1145 (3)	0.24879 (6)	0.09661 (13)	0.0358 (4)
C2	−0.1012 (3)	0.21631 (7)	0.01107 (13)	0.0383 (4)
C3	0.0994 (4)	0.17495 (7)	0.02531 (14)	0.0428 (4)
H3	0.1000	0.1542	−0.0345	0.051*
C4	0.3006 (3)	0.16426 (7)	0.12888 (14)	0.0414 (4)
C5	0.2925 (3)	0.19620 (7)	0.21530 (14)	0.0432 (5)
H5	0.4233	0.1896	0.2855	0.052*
C6	0.0935 (3)	0.23774 (7)	0.19898 (13)	0.0394 (4)
C7	−0.3211 (4)	0.29564 (7)	0.07705 (15)	0.0454 (5)
H7A	−0.3674	0.3038	0.1441	0.054*
H7B	−0.5092	0.2871	0.0207	0.054*
C8	−0.1801 (4)	0.34346 (7)	0.04135 (17)	0.0557 (5)
H8A	0.0020	0.3528	0.0999	0.067*
H8B	−0.1210	0.3341	−0.0226	0.067*
C9	−0.3832 (5)	0.39095 (8)	0.0136 (2)	0.0756 (7)
H9A	−0.5625	0.3822	−0.0468	0.091*
H9B	−0.4472	0.3999	0.0766	0.091*
C10	−0.2332 (6)	0.43810 (9)	−0.0182 (3)	0.1069 (10)
H10A	−0.0721	0.4500	0.0445	0.160*
H10B	−0.3790	0.4657	−0.0430	0.160*
H10C	−0.1529	0.4286	−0.0762	0.160*
C11	0.5085 (4)	0.11754 (7)	0.14655 (16)	0.0523 (5)
H11A	0.6758	0.1228	0.2134	0.063*
H11B	0.5910	0.1151	0.0858	0.063*
C12	0.3515 (4)	0.06650 (7)	0.15543 (18)	0.0604 (6)
H12A	0.1767	0.0628	0.0905	0.073*
H12B	0.2783	0.0687	0.2185	0.073*
C13	0.5435 (4)	0.01760 (7)	0.16697 (17)	0.0594 (5)
H13A	0.6171	0.0153	0.1040	0.071*
H13B	0.7178	0.0211	0.2322	0.071*
C14	0.3833 (5)	−0.03251 (8)	0.1752 (2)	0.0848 (8)
H14A	0.3137	−0.0304	0.2391	0.102*
H14B	0.2060	−0.0354	0.1109	0.102*
C15	0.5672 (6)	−0.08146 (9)	0.1840 (2)	0.0970 (9)
H15A	0.6319	−0.0848	0.1200	0.145*
H15B	0.4468	−0.1114	0.1892	0.145*
H15C	0.7409	−0.0796	0.2485	0.145*

	U11	U22	U33	U12	U13	U23
O1	0.0453 (7)	0.0768 (9)	0.0399 (8)	0.0016 (7)	0.0069 (6)	−0.0146 (7)
O2	0.0446 (7)	0.0744 (9)	0.0314 (7)	0.0080 (6)	0.0052 (5)	0.0047 (7)
C1	0.0292 (8)	0.0443 (10)	0.0339 (9)	−0.0028 (7)	0.0099 (7)	0.0024 (8)
C2	0.0316 (8)	0.0488 (10)	0.0311 (9)	−0.0041 (8)	0.0046 (7)	0.0039 (8)
C3	0.0432 (9)	0.0484 (11)	0.0367 (10)	0.0004 (9)	0.0120 (8)	−0.0031 (8)
C4	0.0345 (8)	0.0442 (10)	0.0442 (11)	−0.0015 (8)	0.0104 (8)	0.0053 (8)
C5	0.0333 (9)	0.0552 (11)	0.0350 (10)	−0.0007 (8)	0.0018 (7)	0.0063 (9)
C6	0.0342 (9)	0.0511 (11)	0.0325 (10)	−0.0050 (8)	0.0101 (7)	−0.0029 (8)
C7	0.0369 (9)	0.0538 (11)	0.0450 (11)	0.0028 (8)	0.0119 (8)	−0.0009 (9)
C8	0.0491 (10)	0.0527 (12)	0.0640 (13)	0.0043 (9)	0.0156 (9)	0.0016 (10)
C9	0.0815 (15)	0.0596 (14)	0.0889 (17)	0.0159 (12)	0.0310 (13)	0.0062 (13)
C10	0.131 (2)	0.0567 (16)	0.138 (3)	0.0108 (15)	0.050 (2)	0.0224 (16)
C11	0.0440 (10)	0.0511 (11)	0.0592 (12)	0.0069 (9)	0.0124 (8)	0.0052 (10)
C12	0.0517 (11)	0.0524 (12)	0.0753 (14)	0.0037 (9)	0.0168 (10)	0.0068 (11)
C13	0.0604 (12)	0.0521 (12)	0.0638 (14)	0.0075 (10)	0.0167 (10)	0.0006 (10)
C14	0.0828 (16)	0.0543 (14)	0.113 (2)	0.0030 (12)	0.0242 (15)	0.0058 (13)
C15	0.118 (2)	0.0560 (15)	0.113 (2)	0.0078 (14)	0.0293 (17)	−0.0002 (14)

O1—C6	1.3899 (19)	C9—H9A	0.9700
O1—H1	0.8200	C9—H9B	0.9700
O2—C2	1.3924 (18)	C10—H10A	0.9600
O2—H2	0.8200	C10—H10B	0.9600
C1—C2	1.388 (2)	C10—H10C	0.9600
C1—C6	1.394 (2)	C11—C12	1.512 (3)
C1—C7	1.503 (2)	C11—H11A	0.9700
C2—C3	1.381 (2)	C11—H11B	0.9700
C3—C4	1.391 (2)	C12—C13	1.512 (3)
C3—H3	0.9300	C12—H12A	0.9700
C4—C5	1.382 (2)	C12—H12B	0.9700
C4—C11	1.505 (2)	C13—C14	1.497 (3)
C5—C6	1.378 (2)	C13—H13A	0.9700
C5—H5	0.9300	C13—H13B	0.9700
C7—C8	1.519 (3)	C14—C15	1.496 (3)
C7—H7A	0.9700	C14—H14A	0.9700
C7—H7B	0.9700	C14—H14B	0.9700
C8—C9	1.507 (3)	C15—H15A	0.9600
C8—H8A	0.9700	C15—H15B	0.9600
C8—H8B	0.9700	C15—H15C	0.9600
C9—C10	1.506 (3)
C6—O1—H1	109.5	H9A—C9—H9B	107.8
C2—O2—H2	109.5	C9—C10—H10A	109.5
C2—C1—C6	115.59 (15)	C9—C10—H10B	109.5
C2—C1—C7	121.63 (14)	H10A—C10—H10B	109.5
C6—C1—C7	122.55 (15)	C9—C10—H10C	109.5
C3—C2—C1	122.97 (15)	H10A—C10—H10C	109.5
C3—C2—O2	119.73 (15)	H10B—C10—H10C	109.5
C1—C2—O2	117.29 (14)	C4—C11—C12	112.77 (14)
C2—C3—C4	120.13 (16)	C4—C11—H11A	109.0
C2—C3—H3	119.9	C12—C11—H11A	109.0
C4—C3—H3	119.9	C4—C11—H11B	109.0
C5—C4—C3	117.98 (15)	C12—C11—H11B	109.0
C5—C4—C11	121.38 (16)	H11A—C11—H11B	107.8
C3—C4—C11	120.57 (17)	C11—C12—C13	115.46 (16)
C6—C5—C4	120.95 (15)	C11—C12—H12A	108.4
C6—C5—H5	119.5	C13—C12—H12A	108.4
C4—C5—H5	119.5	C11—C12—H12B	108.4
C5—C6—O1	120.90 (14)	C13—C12—H12B	108.4
C5—C6—C1	122.35 (16)	H12A—C12—H12B	107.5
O1—C6—C1	116.74 (14)	C14—C13—C12	114.58 (17)
C1—C7—C8	111.85 (14)	C14—C13—H13A	108.6
C1—C7—H7A	109.2	C12—C13—H13A	108.6
C8—C7—H7A	109.2	C14—C13—H13B	108.6
C1—C7—H7B	109.2	C12—C13—H13B	108.6
C8—C7—H7B	109.2	H13A—C13—H13B	107.6
H7A—C7—H7B	107.9	C15—C14—C13	115.4 (2)
C9—C8—C7	114.57 (16)	C15—C14—H14A	108.4
C9—C8—H8A	108.6	C13—C14—H14A	108.4
C7—C8—H8A	108.6	C15—C14—H14B	108.4
C9—C8—H8B	108.6	C13—C14—H14B	108.4
C7—C8—H8B	108.6	H14A—C14—H14B	107.5
H8A—C8—H8B	107.6	C14—C15—H15A	109.5
C10—C9—C8	113.16 (18)	C14—C15—H15B	109.5
C10—C9—H9A	108.9	H15A—C15—H15B	109.5
C8—C9—H9A	108.9	C14—C15—H15C	109.5
C10—C9—H9B	108.9	H15A—C15—H15C	109.5
C8—C9—H9B	108.9	H15B—C15—H15C	109.5
C6—C1—C2—C3	1.2 (2)	C7—C1—C6—C5	−176.77 (15)
C7—C1—C2—C3	175.85 (15)	C2—C1—C6—O1	176.89 (14)
C6—C1—C2—O2	−177.88 (13)	C7—C1—C6—O1	2.3 (2)
C7—C1—C2—O2	−3.2 (2)	C2—C1—C7—C8	−83.9 (2)
C1—C2—C3—C4	−0.1 (2)	C6—C1—C7—C8	90.4 (2)
O2—C2—C3—C4	179.01 (14)	C1—C7—C8—C9	176.41 (17)
C2—C3—C4—C5	−0.2 (2)	C7—C8—C9—C10	178.26 (19)
C2—C3—C4—C11	176.65 (15)	C5—C4—C11—C12	98.0 (2)
C3—C4—C5—C6	−0.8 (2)	C3—C4—C11—C12	−78.7 (2)
C11—C4—C5—C6	−177.58 (15)	C4—C11—C12—C13	176.76 (17)
C4—C5—C6—O1	−177.00 (15)	C11—C12—C13—C14	−179.8 (2)
C4—C5—C6—C1	2.0 (2)	C12—C13—C14—C15	178.6 (2)
C2—C1—C6—C5	−2.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.96	2.767 (2)	167
O2—H2···O1ii	0.82	1.95	2.750 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.96	2.767 (2)	167
O2—H2⋯O1ii	0.82	1.95	2.750 (2)	165

Symmetry codes: (i) ; (ii) .