1-{2-Hy-droxy-6-[3-(pyrrol-1-yl)prop-oxy]phen-yl}ethanone.

In the title compound, C(15)H(17)NO(3), the mean planes of the pyrrole and benzene rings form a dihedral angle of 81.92 (7)°. The mol-ecule contains an intra-molecular O-H⋯O hydrogen bond. In the crystal, weak C-H⋯π inter-actions link the mol-ecules into chains along [010].

Related literature

For the synthesis and applications of similar compounds and their derivatives, see: Wu & Lu (2003 ▶); Saraswat et al. (2006 ▶); Smith et al. (2003 ▶); Dong et al. (2010 ▶); Deronzier & Moutet (1996 ▶); MacDearmid (2001 ▶); Srinivasan et al. (1986 ▶); Coche-Guerente et al. (1995 ▶); Ourari et al. (2008 ▶); Khedkar & Radhakrishnan (1997 ▶); Huo et al. (1999 ▶).

Experimental

Crystal data

C15H17NO3

M = 259.3

Triclinic,

a = 7.741 (2) Å

b = 9.230 (1) Å

c = 10.464 (1) Å

α = 71.63 (2)°

β = 75.222 (1)°

γ = 82.081 (1)°

V = 684.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.15 × 0.08 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

4238 measured reflections

2586 independent reflections

1995 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.128

S = 1.05

2586 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010641/lh5428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010641/lh5428Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010641/lh5428Isup3.cml

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

C15H17NO3	Z = 2
Mr = 259.3	F(000) = 276
Triclinic, P1	Dx = 1.258 Mg m−3
a = 7.741 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.230 (1) Å	Cell parameters from 2211 reflections
c = 10.464 (1) Å	θ = 1.0–26.4°
α = 71.63 (2)°	µ = 0.09 mm−1
β = 75.222 (1)°	T = 295 K
γ = 82.081 (1)°	Plate, white
V = 684.7 (2) Å3	0.15 × 0.08 × 0.04 mm

Nonius KappaCCD diffractometer	1995 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.020
Graphite monochromator	θmax = 26.4°, θmin = 3.1°
Detector resolution: 9 pixels mm-1	h = −8→8
CCD rotation images, thick slices scans	k = −11→11
4238 measured reflections	l = −11→13
2586 independent reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.0857P] where P = (Fo2 + 2Fc2)/3
2586 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 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
C1	0.22766 (19)	0.41969 (15)	0.52869 (14)	0.0461 (3)
C2	0.13789 (18)	0.35148 (15)	0.66752 (14)	0.0462 (3)
C3	0.1027 (2)	0.19569 (17)	0.70372 (16)	0.0543 (4)
C4	0.1559 (2)	0.11311 (18)	0.60838 (19)	0.0641 (4)
H4	0.1327	0.0104	0.6342	0.077*
C5	0.2426 (2)	0.18421 (18)	0.47626 (18)	0.0653 (5)
H5	0.278	0.1286	0.4126	0.078*
C6	0.2790 (2)	0.33656 (17)	0.43500 (16)	0.0571 (4)
H6	0.3378	0.3828	0.3445	0.069*
C7	0.0815 (2)	0.43219 (18)	0.77474 (15)	0.0523 (4)
C8	0.1265 (2)	0.59134 (19)	0.75300 (18)	0.0631 (4)
H8A	0.0639	0.6615	0.6879	0.095*
H8B	0.2531	0.5999	0.7177	0.095*
H8C	0.0914	0.6152	0.8393	0.095*
C9	0.3468 (2)	0.64362 (16)	0.35422 (14)	0.0503 (4)
H9A	0.2802	0.633	0.2911	0.06*
H9B	0.4663	0.5963	0.3328	0.06*
C10	0.3574 (2)	0.81022 (16)	0.33794 (15)	0.0503 (4)
H10A	0.4256	0.8209	0.4001	0.06*
H10B	0.2381	0.8572	0.3608	0.06*
C11	0.4473 (2)	0.88841 (17)	0.19002 (16)	0.0605 (4)
H11A	0.5719	0.851	0.1736	0.073*
H11B	0.3915	0.8598	0.1291	0.073*
C12	0.2945 (2)	1.14975 (17)	0.12267 (16)	0.0559 (4)
H12	0.1838	1.1193	0.1252	0.067*
C13	0.3403 (2)	1.29658 (18)	0.08711 (17)	0.0612 (4)
H13	0.2669	1.3843	0.0614	0.073*
C14	0.5179 (3)	1.29123 (19)	0.09628 (18)	0.0657 (5)
H14	0.5847	1.3749	0.0775	0.079*
C15	0.5757 (2)	1.14127 (19)	0.13775 (17)	0.0621 (4)
H15	0.6892	1.1045	0.1524	0.074*
N1	0.43895 (17)	1.05482 (13)	0.15398 (12)	0.0517 (3)
O1	0.25933 (15)	0.57023 (11)	0.49358 (10)	0.0550 (3)
O2	−0.00716 (18)	0.36498 (15)	0.89029 (12)	0.0776 (4)
O3	0.01756 (18)	0.11918 (14)	0.83236 (13)	0.0736 (4)
H3	−0.005 (3)	0.197 (2)	0.882 (2)	0.088*

	U11	U22	U33	U12	U13	U23
C1	0.0511 (8)	0.0426 (7)	0.0465 (8)	−0.0031 (6)	−0.0141 (6)	−0.0132 (6)
C2	0.0462 (8)	0.0477 (8)	0.0460 (8)	−0.0038 (6)	−0.0141 (6)	−0.0121 (6)
C3	0.0558 (9)	0.0518 (8)	0.0538 (9)	−0.0111 (6)	−0.0175 (6)	−0.0059 (7)
C4	0.0801 (12)	0.0467 (8)	0.0701 (11)	−0.0104 (7)	−0.0237 (9)	−0.0155 (8)
C5	0.0868 (13)	0.0530 (9)	0.0645 (10)	−0.0031 (8)	−0.0200 (9)	−0.0269 (8)
C6	0.0730 (11)	0.0512 (8)	0.0489 (9)	−0.0053 (7)	−0.0107 (7)	−0.0188 (7)
C7	0.0480 (8)	0.0637 (9)	0.0467 (8)	−0.0041 (6)	−0.0105 (6)	−0.0180 (7)
C8	0.0653 (10)	0.0705 (11)	0.0600 (10)	−0.0061 (8)	−0.0056 (7)	−0.0340 (8)
C9	0.0562 (9)	0.0495 (8)	0.0430 (8)	−0.0050 (6)	−0.0084 (6)	−0.0118 (6)
C10	0.0575 (9)	0.0465 (8)	0.0455 (8)	−0.0052 (6)	−0.0110 (6)	−0.0111 (6)
C11	0.0778 (11)	0.0459 (8)	0.0492 (9)	−0.0042 (7)	−0.0038 (7)	−0.0103 (7)
C12	0.0514 (9)	0.0570 (9)	0.0536 (9)	−0.0068 (7)	−0.0066 (6)	−0.0108 (7)
C13	0.0689 (11)	0.0508 (9)	0.0560 (9)	−0.0013 (7)	−0.0079 (7)	−0.0105 (7)
C14	0.0820 (12)	0.0549 (9)	0.0598 (10)	−0.0214 (8)	−0.0160 (8)	−0.0093 (8)
C15	0.0612 (10)	0.0631 (10)	0.0592 (10)	−0.0127 (7)	−0.0178 (7)	−0.0068 (8)
N1	0.0588 (8)	0.0448 (7)	0.0453 (7)	−0.0061 (5)	−0.0065 (5)	−0.0076 (5)
O1	0.0754 (7)	0.0439 (6)	0.0426 (6)	−0.0116 (5)	−0.0041 (5)	−0.0123 (4)
O2	0.0910 (9)	0.0849 (9)	0.0502 (7)	−0.0214 (7)	0.0058 (6)	−0.0209 (6)
O3	0.0885 (9)	0.0633 (8)	0.0604 (8)	−0.0263 (6)	−0.0079 (6)	−0.0040 (6)

C1—O1	1.3609 (17)	C9—H9A	0.97
C1—C6	1.378 (2)	C9—H9B	0.97
C1—C2	1.421 (2)	C10—C11	1.512 (2)
C2—C3	1.413 (2)	C10—H10A	0.97
C2—C7	1.480 (2)	C10—H10B	0.97
C3—O3	1.3496 (19)	C11—N1	1.4579 (18)
C3—C4	1.389 (2)	C11—H11A	0.97
C4—C5	1.367 (2)	C11—H11B	0.97
C4—H4	0.93	C12—C13	1.359 (2)
C5—C6	1.381 (2)	C12—N1	1.364 (2)
C5—H5	0.93	C12—H12	0.93
C6—H6	0.93	C13—C14	1.396 (2)
C7—O2	1.2406 (18)	C13—H13	0.93
C7—C8	1.490 (2)	C14—C15	1.362 (2)
C8—H8A	0.96	C14—H14	0.93
C8—H8B	0.96	C15—N1	1.357 (2)
C8—H8C	0.96	C15—H15	0.93
C9—O1	1.4297 (17)	O3—H3	0.98 (2)
C9—C10	1.5042 (19)
O1—C1—C6	122.13 (13)	C10—C9—H9B	109.9
O1—C1—C2	116.67 (12)	H9A—C9—H9B	108.3
C6—C1—C2	121.19 (13)	C9—C10—C11	108.84 (12)
C3—C2—C1	116.77 (13)	C9—C10—H10A	109.9
C3—C2—C7	118.82 (13)	C11—C10—H10A	109.9
C1—C2—C7	124.41 (13)	C9—C10—H10B	109.9
O3—C3—C4	116.60 (14)	C11—C10—H10B	109.9
O3—C3—C2	121.99 (15)	H10A—C10—H10B	108.3
C4—C3—C2	121.41 (14)	N1—C11—C10	114.44 (13)
C5—C4—C3	119.40 (14)	N1—C11—H11A	108.7
C5—C4—H4	120.3	C10—C11—H11A	108.7
C3—C4—H4	120.3	N1—C11—H11B	108.7
C4—C5—C6	121.59 (15)	C10—C11—H11B	108.7
C4—C5—H5	119.2	H11A—C11—H11B	107.6
C6—C5—H5	119.2	C13—C12—N1	108.26 (14)
C1—C6—C5	119.62 (15)	C13—C12—H12	125.9
C1—C6—H6	120.2	N1—C12—H12	125.9
C5—C6—H6	120.2	C12—C13—C14	107.29 (15)
O2—C7—C2	119.14 (14)	C12—C13—H13	126.4
O2—C7—C8	117.11 (14)	C14—C13—H13	126.4
C2—C7—C8	123.74 (13)	C15—C14—C13	107.58 (15)
C7—C8—H8A	109.5	C15—C14—H14	126.2
C7—C8—H8B	109.5	C13—C14—H14	126.2
H8A—C8—H8B	109.5	N1—C15—C14	108.19 (15)
C7—C8—H8C	109.5	N1—C15—H15	125.9
H8A—C8—H8C	109.5	C14—C15—H15	125.9
H8B—C8—H8C	109.5	C15—N1—C12	108.68 (13)
O1—C9—C10	108.82 (11)	C15—N1—C11	125.99 (14)
O1—C9—H9A	109.9	C12—N1—C11	125.22 (13)
C10—C9—H9A	109.9	C1—O1—C9	118.35 (11)
O1—C9—H9B	109.9	C3—O3—H3	102.9 (12)
O1—C1—C2—C3	179.16 (12)	C3—C2—C7—C8	173.87 (14)
C6—C1—C2—C3	−0.6 (2)	C1—C2—C7—C8	−5.6 (2)
O1—C1—C2—C7	−1.4 (2)	O1—C9—C10—C11	−179.11 (12)
C6—C1—C2—C7	178.83 (13)	C9—C10—C11—N1	170.05 (13)
C1—C2—C3—O3	−179.70 (13)	N1—C12—C13—C14	0.30 (18)
C7—C2—C3—O3	0.8 (2)	C12—C13—C14—C15	−0.2 (2)
C1—C2—C3—C4	0.9 (2)	C13—C14—C15—N1	0.10 (19)
C7—C2—C3—C4	−178.57 (13)	C14—C15—N1—C12	0.08 (18)
O3—C3—C4—C5	179.94 (16)	C14—C15—N1—C11	176.39 (15)
C2—C3—C4—C5	−0.7 (3)	C13—C12—N1—C15	−0.24 (18)
C3—C4—C5—C6	0.1 (3)	C13—C12—N1—C11	−176.59 (14)
O1—C1—C6—C5	−179.71 (14)	C10—C11—N1—C15	104.65 (18)
C2—C1—C6—C5	0.1 (2)	C10—C11—N1—C12	−79.63 (19)
C4—C5—C6—C1	0.2 (3)	C6—C1—O1—C9	0.8 (2)
C3—C2—C7—O2	−5.5 (2)	C2—C1—O1—C9	−179.01 (12)
C1—C2—C7—O2	174.99 (14)	C10—C9—O1—C1	176.69 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.98 (2)	1.578 (19)	2.498 (2)	153.4 (18)
C5—H5···Cgi	0.93	2.90	3.641 (2)	138
C11—H11B···Cgii	0.97	2.74	3.3973 (19)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg is is the centroid of the N1/C12–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.98 (2)	1.578 (19)	2.498 (2)	153.4 (18)
C5—H5⋯Cgi	0.93	2.90	3.641 (2)	138
C11—H11B⋯Cgii	0.97	2.74	3.3973 (19)	125

Symmetry codes: (i) ; (ii) .