(E)-3-(4-Decyl-oxyphen-yl)-1-(2-hydroxy-phen-yl)prop-2-en-1-one.

In the title compound, C(25)H(32)O(3), the enone group is in an s-cis configuration. The dihedral angle between the benzene rings is 8.84 (7)°. An intra-molecular O-H⋯O inter-action between the keto and hydr-oxy groups forms an S(6) ring motif. Inter-molecular C-H⋯O inter-actions link the mol-ecules into supra-molecular chains along the c axis which are subsequently stacked down the b axis; the crystal structure is further consolidated by C-H⋯π inter-actions.

Related literature

For general background, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Satyanarayana et al. (2004 ▶); Won et al. (2005 ▶); Zhao et al. (2005 ▶). For related structures, see: Ng, Razak et al. (2006 ▶); Ng, Patil et al. (2006 ▶); Razak et al. (2009 ▶); Ngaini et al. (2009 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, 1986 ▶.

Experimental

Crystal data

C25H32O3

M = 380.51

Monoclinic,

a = 21.2700 (4) Å

b = 7.6779 (2) Å

c = 13.2330 (3) Å

β = 101.720 (1)°

V = 2116.01 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.44 × 0.28 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.967, T max = 0.997

25687 measured reflections

6221 independent reflections

4014 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.165

S = 1.04

6221 reflections

258 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010848/tk2402sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010848/tk2402Isup2.hkl

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

C25H32O3	F(000) = 824
Mr = 380.51	Dx = 1.194 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3600 reflections
a = 21.2700 (4) Å	θ = 2.8–30.1°
b = 7.6779 (2) Å	µ = 0.08 mm−1
c = 13.2330 (3) Å	T = 100 K
β = 101.720 (1)°	Plate, yellow
V = 2116.01 (8) Å3	0.44 × 0.28 × 0.04 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	6221 independent reflections
Radiation source: sealed tube	4014 reflections with I > 2σ(I)
graphite	Rint = 0.056
π and ω scans	θmax = 30.1°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −30→30
Tmin = 0.967, Tmax = 0.997	k = −10→10
25687 measured reflections	l = −18→18

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.085P)2] where P = (Fo2 + 2Fc2)/3
6221 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.77177 (6)	−0.18603 (17)	1.07201 (8)	0.0262 (3)
O2	0.67717 (5)	−0.08052 (16)	0.93853 (8)	0.0229 (3)
O3	0.46966 (5)	0.31479 (15)	0.38134 (8)	0.0184 (3)
C1	0.80643 (7)	−0.1716 (2)	0.99763 (11)	0.0190 (3)
C2	0.87159 (7)	−0.2144 (2)	1.02373 (12)	0.0221 (4)
H2A	0.8895	−0.2502	1.0905	0.026*
C3	0.90932 (8)	−0.2037 (2)	0.95104 (13)	0.0238 (4)
H3A	0.9527	−0.2317	0.9691	0.029*
C4	0.88302 (7)	−0.1510 (2)	0.85025 (12)	0.0243 (4)
H4A	0.9087	−0.1447	0.8012	0.029*
C5	0.81885 (7)	−0.1087 (2)	0.82397 (12)	0.0202 (4)
H5A	0.8015	−0.0748	0.7566	0.024*
C6	0.77893 (7)	−0.1153 (2)	0.89626 (11)	0.0164 (3)
C7	0.71034 (7)	−0.0670 (2)	0.87122 (11)	0.0168 (3)
C8	0.68075 (7)	−0.0001 (2)	0.76851 (11)	0.0170 (3)
H8A	0.7050	0.0083	0.7176	0.020*
C9	0.61889 (7)	0.0488 (2)	0.74806 (11)	0.0162 (3)
H9A	0.5973	0.0365	0.8021	0.019*
C10	0.58106 (7)	0.1188 (2)	0.65252 (11)	0.0148 (3)
C11	0.60383 (7)	0.1283 (2)	0.56004 (11)	0.0173 (3)
H11A	0.6451	0.0898	0.5583	0.021*
C12	0.56528 (7)	0.1943 (2)	0.47184 (11)	0.0181 (3)
H12A	0.5806	0.1993	0.4109	0.022*
C13	0.50347 (7)	0.2538 (2)	0.47327 (11)	0.0155 (3)
C14	0.48019 (7)	0.2480 (2)	0.56425 (11)	0.0169 (3)
H14A	0.4393	0.2891	0.5661	0.020*
C15	0.51927 (7)	0.1794 (2)	0.65231 (11)	0.0178 (3)
H15A	0.5037	0.1738	0.7130	0.021*
C16	0.40477 (7)	0.3738 (2)	0.37618 (11)	0.0166 (3)
H16A	0.4040	0.4690	0.4241	0.020*
H16B	0.3784	0.2798	0.3935	0.020*
C17	0.37994 (7)	0.4340 (2)	0.26649 (11)	0.0167 (3)
H17A	0.3836	0.3389	0.2198	0.020*
H17B	0.4068	0.5286	0.2512	0.020*
C18	0.31030 (7)	0.4956 (2)	0.24639 (11)	0.0174 (3)
H18A	0.3063	0.5922	0.2919	0.021*
H18B	0.2830	0.4018	0.2613	0.021*
C19	0.28817 (7)	0.5531 (2)	0.13439 (11)	0.0171 (3)
H19A	0.3153	0.6484	0.1212	0.021*
H19B	0.2946	0.4571	0.0899	0.021*
C20	0.21838 (7)	0.6114 (2)	0.10436 (11)	0.0179 (3)
H20A	0.2113	0.7086	0.1476	0.022*
H20B	0.1906	0.5167	0.1161	0.022*
C21	0.20115 (7)	0.6662 (2)	−0.00900 (11)	0.0197 (3)
H21A	0.2293	0.7608	−0.0197	0.024*
H21B	0.2095	0.5690	−0.0512	0.024*
C22	0.13201 (7)	0.7246 (2)	−0.04652 (11)	0.0198 (3)
H22A	0.1231	0.8218	−0.0048	0.024*
H22B	0.1034	0.6300	−0.0375	0.024*
C23	0.11847 (7)	0.7792 (2)	−0.15963 (12)	0.0210 (4)
H23A	0.1467	0.8751	−0.1677	0.025*
H23B	0.1289	0.6826	−0.2006	0.025*
C24	0.04954 (7)	0.8345 (2)	−0.20226 (12)	0.0223 (4)
H24A	0.0400	0.9375	−0.1657	0.027*
H24B	0.0208	0.7424	−0.1899	0.027*
C25	0.03726 (8)	0.8736 (3)	−0.31744 (13)	0.0296 (4)
H25A	−0.0062	0.9124	−0.3402	0.044*
H25B	0.0441	0.7700	−0.3544	0.044*
H25C	0.0662	0.9630	−0.3304	0.044*
H1O1	0.7313 (10)	−0.153 (3)	1.0406 (17)	0.053 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0252 (6)	0.0380 (8)	0.0154 (5)	0.0058 (6)	0.0043 (4)	0.0038 (5)
O2	0.0205 (6)	0.0322 (7)	0.0166 (5)	0.0022 (5)	0.0052 (4)	0.0040 (5)
O3	0.0157 (5)	0.0255 (7)	0.0137 (5)	0.0054 (5)	0.0025 (4)	0.0040 (4)
C1	0.0206 (8)	0.0206 (9)	0.0152 (7)	0.0009 (7)	0.0024 (6)	−0.0017 (6)
C2	0.0218 (8)	0.0255 (10)	0.0162 (7)	0.0055 (7)	−0.0025 (6)	0.0014 (6)
C3	0.0182 (8)	0.0260 (10)	0.0258 (8)	0.0050 (7)	0.0008 (6)	−0.0011 (7)
C4	0.0202 (8)	0.0302 (10)	0.0234 (8)	0.0027 (8)	0.0066 (6)	0.0020 (7)
C5	0.0207 (8)	0.0217 (9)	0.0178 (7)	0.0012 (7)	0.0027 (6)	0.0028 (6)
C6	0.0160 (7)	0.0162 (8)	0.0161 (7)	0.0003 (6)	0.0009 (5)	0.0002 (6)
C7	0.0180 (7)	0.0154 (8)	0.0164 (7)	−0.0009 (6)	0.0020 (5)	−0.0005 (6)
C8	0.0191 (7)	0.0172 (8)	0.0147 (7)	−0.0002 (7)	0.0033 (5)	0.0011 (6)
C9	0.0194 (7)	0.0155 (8)	0.0139 (7)	−0.0026 (6)	0.0039 (5)	−0.0023 (6)
C10	0.0151 (7)	0.0147 (8)	0.0140 (6)	−0.0009 (6)	0.0018 (5)	−0.0003 (6)
C11	0.0155 (7)	0.0187 (9)	0.0181 (7)	0.0020 (6)	0.0041 (5)	−0.0015 (6)
C12	0.0187 (7)	0.0221 (9)	0.0146 (7)	0.0018 (7)	0.0062 (5)	0.0011 (6)
C13	0.0169 (7)	0.0152 (8)	0.0136 (7)	0.0003 (6)	0.0016 (5)	−0.0003 (6)
C14	0.0135 (7)	0.0204 (9)	0.0170 (7)	0.0015 (6)	0.0034 (5)	−0.0016 (6)
C15	0.0167 (7)	0.0230 (9)	0.0144 (7)	−0.0017 (7)	0.0048 (5)	−0.0004 (6)
C16	0.0131 (7)	0.0211 (9)	0.0159 (7)	0.0018 (6)	0.0036 (5)	0.0008 (6)
C17	0.0165 (7)	0.0180 (8)	0.0154 (7)	0.0013 (6)	0.0024 (5)	0.0010 (6)
C18	0.0162 (7)	0.0207 (9)	0.0153 (7)	0.0017 (7)	0.0027 (5)	0.0016 (6)
C19	0.0161 (7)	0.0197 (9)	0.0154 (7)	0.0004 (6)	0.0030 (5)	0.0018 (6)
C20	0.0168 (7)	0.0190 (9)	0.0178 (7)	0.0006 (7)	0.0028 (5)	0.0007 (6)
C21	0.0179 (7)	0.0232 (9)	0.0175 (7)	0.0037 (7)	0.0023 (6)	0.0015 (6)
C22	0.0192 (7)	0.0213 (9)	0.0186 (7)	0.0018 (7)	0.0029 (6)	0.0009 (6)
C23	0.0194 (8)	0.0236 (9)	0.0191 (7)	0.0021 (7)	0.0016 (6)	0.0005 (6)
C24	0.0180 (7)	0.0244 (10)	0.0228 (8)	0.0023 (7)	0.0005 (6)	0.0014 (7)
C25	0.0279 (9)	0.0333 (11)	0.0238 (8)	0.0024 (8)	−0.0038 (7)	0.0034 (7)

O1—C1	1.3488 (18)	C16—C17	1.5126 (19)
O1—H1O1	0.91 (2)	C16—H16A	0.9700
O2—C7	1.2479 (17)	C16—H16B	0.9700
O3—C13	1.3643 (17)	C17—C18	1.526 (2)
O3—C16	1.4411 (17)	C17—H17A	0.9700
C1—C2	1.398 (2)	C17—H17B	0.9700
C1—C6	1.418 (2)	C18—C19	1.5263 (19)
C2—C3	1.375 (2)	C18—H18A	0.9700
C2—H2A	0.9300	C18—H18B	0.9700
C3—C4	1.397 (2)	C19—C20	1.524 (2)
C3—H3A	0.9300	C19—H19A	0.9700
C4—C5	1.377 (2)	C19—H19B	0.9700
C4—H4A	0.9300	C20—C21	1.529 (2)
C5—C6	1.403 (2)	C20—H20A	0.9700
C5—H5A	0.9300	C20—H20B	0.9700
C6—C7	1.476 (2)	C21—C22	1.521 (2)
C7—C8	1.469 (2)	C21—H21A	0.9700
C8—C9	1.342 (2)	C21—H21B	0.9700
C8—H8A	0.9300	C22—C23	1.524 (2)
C9—C10	1.4563 (19)	C22—H22A	0.9700
C9—H9A	0.9300	C22—H22B	0.9700
C10—C15	1.394 (2)	C23—C24	1.520 (2)
C10—C11	1.406 (2)	C23—H23A	0.9700
C11—C12	1.379 (2)	C23—H23B	0.9700
C11—H11A	0.9300	C24—C25	1.523 (2)
C12—C13	1.395 (2)	C24—H24A	0.9700
C12—H12A	0.9300	C24—H24B	0.9700
C13—C14	1.393 (2)	C25—H25A	0.9600
C14—C15	1.390 (2)	C25—H25B	0.9600
C14—H14A	0.9300	C25—H25C	0.9600
C15—H15A	0.9300
C1—O1—H1O1	104.5 (14)	C16—C17—H17A	108.9
C13—O3—C16	118.47 (11)	C18—C17—H17A	108.9
O1—C1—C2	117.51 (14)	C16—C17—H17B	108.9
O1—C1—C6	122.27 (14)	C18—C17—H17B	108.9
C2—C1—C6	120.21 (14)	H17A—C17—H17B	107.7
C3—C2—C1	120.24 (14)	C17—C18—C19	110.85 (12)
C3—C2—H2A	119.9	C17—C18—H18A	109.5
C1—C2—H2A	119.9	C19—C18—H18A	109.5
C2—C3—C4	120.52 (14)	C17—C18—H18B	109.5
C2—C3—H3A	119.7	C19—C18—H18B	109.5
C4—C3—H3A	119.7	H18A—C18—H18B	108.1
C5—C4—C3	119.56 (15)	C20—C19—C18	115.48 (12)
C5—C4—H4A	120.2	C20—C19—H19A	108.4
C3—C4—H4A	120.2	C18—C19—H19A	108.4
C4—C5—C6	121.68 (14)	C20—C19—H19B	108.4
C4—C5—H5A	119.2	C18—C19—H19B	108.4
C6—C5—H5A	119.2	H19A—C19—H19B	107.5
C5—C6—C1	117.76 (13)	C19—C20—C21	111.31 (12)
C5—C6—C7	123.03 (13)	C19—C20—H20A	109.4
C1—C6—C7	119.21 (13)	C21—C20—H20A	109.4
O2—C7—C8	119.42 (13)	C19—C20—H20B	109.4
O2—C7—C6	119.67 (13)	C21—C20—H20B	109.4
C8—C7—C6	120.90 (13)	H20A—C20—H20B	108.0
C9—C8—C7	120.17 (14)	C22—C21—C20	115.12 (12)
C9—C8—H8A	119.9	C22—C21—H21A	108.5
C7—C8—H8A	119.9	C20—C21—H21A	108.5
C8—C9—C10	128.65 (14)	C22—C21—H21B	108.5
C8—C9—H9A	115.7	C20—C21—H21B	108.5
C10—C9—H9A	115.7	H21A—C21—H21B	107.5
C15—C10—C11	118.18 (13)	C21—C22—C23	112.27 (12)
C15—C10—C9	118.64 (13)	C21—C22—H22A	109.2
C11—C10—C9	123.18 (13)	C23—C22—H22A	109.2
C12—C11—C10	120.31 (14)	C21—C22—H22B	109.2
C12—C11—H11A	119.8	C23—C22—H22B	109.2
C10—C11—H11A	119.8	H22A—C22—H22B	107.9
C11—C12—C13	120.56 (13)	C24—C23—C22	114.63 (13)
C11—C12—H12A	119.7	C24—C23—H23A	108.6
C13—C12—H12A	119.7	C22—C23—H23A	108.6
O3—C13—C14	124.49 (13)	C24—C23—H23B	108.6
O3—C13—C12	115.33 (12)	C22—C23—H23B	108.6
C14—C13—C12	120.18 (13)	H23A—C23—H23B	107.6
C15—C14—C13	118.67 (14)	C23—C24—C25	112.51 (14)
C15—C14—H14A	120.7	C23—C24—H24A	109.1
C13—C14—H14A	120.7	C25—C24—H24A	109.1
C14—C15—C10	122.08 (14)	C23—C24—H24B	109.1
C14—C15—H15A	119.0	C25—C24—H24B	109.1
C10—C15—H15A	119.0	H24A—C24—H24B	107.8
O3—C16—C17	106.62 (11)	C24—C25—H25A	109.5
O3—C16—H16A	110.4	C24—C25—H25B	109.5
C17—C16—H16A	110.4	H25A—C25—H25B	109.5
O3—C16—H16B	110.4	C24—C25—H25C	109.5
C17—C16—H16B	110.4	H25A—C25—H25C	109.5
H16A—C16—H16B	108.6	H25B—C25—H25C	109.5
C16—C17—C18	113.54 (12)
O1—C1—C2—C3	179.46 (16)	C9—C10—C11—C12	179.31 (15)
C6—C1—C2—C3	−0.6 (3)	C10—C11—C12—C13	0.5 (2)
C1—C2—C3—C4	−0.4 (3)	C16—O3—C13—C14	−1.6 (2)
C2—C3—C4—C5	0.4 (3)	C16—O3—C13—C12	178.28 (13)
C3—C4—C5—C6	0.6 (3)	C11—C12—C13—O3	−179.46 (14)
C4—C5—C6—C1	−1.5 (2)	C11—C12—C13—C14	0.4 (2)
C4—C5—C6—C7	178.57 (16)	O3—C13—C14—C15	178.78 (14)
O1—C1—C6—C5	−178.55 (15)	C12—C13—C14—C15	−1.1 (2)
C2—C1—C6—C5	1.5 (2)	C13—C14—C15—C10	0.9 (2)
O1—C1—C6—C7	1.4 (2)	C11—C10—C15—C14	0.0 (2)
C2—C1—C6—C7	−178.58 (15)	C9—C10—C15—C14	−179.99 (14)
C5—C6—C7—O2	178.04 (16)	C13—O3—C16—C17	179.70 (13)
C1—C6—C7—O2	−1.9 (2)	O3—C16—C17—C18	178.01 (13)
C5—C6—C7—C8	−3.0 (2)	C16—C17—C18—C19	−179.58 (13)
C1—C6—C7—C8	177.06 (15)	C17—C18—C19—C20	177.93 (14)
O2—C7—C8—C9	1.2 (2)	C18—C19—C20—C21	179.96 (14)
C6—C7—C8—C9	−177.73 (15)	C19—C20—C21—C22	179.28 (14)
C7—C8—C9—C10	179.58 (15)	C20—C21—C22—C23	179.36 (14)
C8—C9—C10—C15	−172.82 (16)	C21—C22—C23—C24	178.50 (14)
C8—C9—C10—C11	7.2 (3)	C22—C23—C24—C25	−175.39 (15)
C15—C10—C11—C12	−0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.91 (2)	1.68 (2)	2.526 (2)	152 (2)
C15—H15A···O3i	0.93	2.48	3.406 (2)	174
C20—H20B···Cg1ii	0.97	2.85	3.702 (2)	147
C22—H22A···Cg1iii	0.97	2.84	3.712 (2)	149
C16—H16A···Cg2iii	0.97	2.87	3.596 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.91 (2)	1.68 (2)	2.526 (2)	152 (2)
C15—H15A⋯O3i	0.93	2.48	3.406 (2)	174
C20—H20B⋯Cg1ii	0.97	2.85	3.702 (2)	147
C22—H22A⋯Cg1iii	0.97	2.84	3.712 (2)	149
C16—H16A⋯Cg2iii	0.97	2.87	3.596 (2)	132

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.