1-[4-(4-Hy-droxy-phen-yl)piperazin-1-yl]ethanone.

In the title compound, C12H16N2O2, the piperazine ring has a chair conformation. The dihedral angle between the mean planes of the benzene ring and the acetyl group is 48.7 (1)°. In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds, forming chains propagating along [010].

Related literature

For the biological activity of piperazine derivatives, see: Bogatcheva et al. (2006 ▶); Brockunier et al. (2004 ▶); Elliott (2011 ▶); Kharb et al. (2012 ▶). For the crystal structures of related compounds, see: Dayananda et al. (2012 ▶); Kavitha et al. (2013a ▶,b ▶); Peeters et al. (1979 ▶, 2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H16N2O2

M = 220.27

Monoclinic,

a = 6.13183 (19) Å

b = 12.0106 (4) Å

c = 14.8704 (5) Å

β = 94.025 (3)°

V = 1092.46 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.75 mm−1

T = 173 K

0.48 × 0.46 × 0.32 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.833, T max = 1.000

6224 measured reflections

2134 independent reflections

1944 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.07

2134 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028031/su2656sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028031/su2656Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028031/su2656Isup3.cml

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

C12H16N2O2	F(000) = 472
Mr = 220.27	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 6.13183 (19) Å	Cell parameters from 3201 reflections
b = 12.0106 (4) Å	θ = 3.7–72.1°
c = 14.8704 (5) Å	µ = 0.75 mm−1
β = 94.025 (3)°	T = 173 K
V = 1092.46 (6) Å3	Block, colourless
Z = 4	0.48 × 0.46 × 0.32 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	2134 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1944 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.025
ω scans	θmax = 72.3°, θmin = 4.7°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −7→5
Tmin = 0.833, Tmax = 1.000	k = −14→14
6224 measured reflections	l = −17→18

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.063P)2 + 0.2496P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2134 reflections	Δρmax = 0.22 e Å−3
147 parameters	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.76473 (18)	−0.03376 (8)	0.41180 (7)	0.0420 (3)
O2	0.92639 (18)	0.80536 (7)	0.30904 (7)	0.0375 (3)
H2	0.8626	0.8514	0.3383	0.056*
N1	0.62601 (17)	0.13923 (9)	0.41758 (7)	0.0273 (3)
N2	0.71764 (16)	0.37192 (8)	0.41491 (7)	0.0244 (3)
C1	0.6095 (2)	0.03108 (10)	0.39631 (8)	0.0285 (3)
C2	0.44858 (19)	0.22001 (10)	0.40349 (9)	0.0299 (3)
H2A	0.3914	0.2384	0.4608	0.036*
H2B	0.3309	0.1879	0.3649	0.036*
C3	0.5312 (2)	0.32459 (10)	0.36038 (9)	0.0305 (3)
H3A	0.5754	0.3072	0.3006	0.037*
H3B	0.4143	0.3791	0.3542	0.037*
C4	0.89577 (19)	0.29095 (10)	0.42176 (8)	0.0262 (3)
H4A	1.0203	0.3222	0.4569	0.031*
H4B	0.9407	0.2738	0.3620	0.031*
C5	0.8215 (2)	0.18508 (10)	0.46652 (9)	0.0290 (3)
H5A	0.9381	0.1304	0.4680	0.035*
H5B	0.7897	0.2012	0.5282	0.035*
C6	0.77423 (19)	0.48149 (10)	0.38735 (8)	0.0238 (3)
C7	0.6271 (2)	0.56832 (10)	0.39795 (8)	0.0276 (3)
H7	0.4959	0.5540	0.4235	0.033*
C8	0.6738 (2)	0.67575 (10)	0.37087 (8)	0.0293 (3)
H8	0.5713	0.7319	0.3766	0.035*
C9	0.8717 (2)	0.70046 (10)	0.33537 (8)	0.0275 (3)
C10	1.0194 (2)	0.61483 (11)	0.32474 (9)	0.0315 (3)
H10	1.1523	0.6299	0.3008	0.038*
C11	0.9702 (2)	0.50671 (10)	0.34968 (9)	0.0290 (3)
H11	1.0700	0.4500	0.3411	0.035*
C12	0.3937 (2)	−0.01011 (11)	0.35382 (10)	0.0366 (3)
H12A	0.4010	−0.0892	0.3450	0.055*
H12B	0.3631	0.0260	0.2967	0.055*
H12C	0.2796	0.0067	0.3927	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0495 (6)	0.0251 (5)	0.0499 (6)	0.0119 (4)	−0.0068 (5)	−0.0033 (4)
O2	0.0524 (6)	0.0219 (5)	0.0390 (5)	−0.0023 (4)	0.0087 (4)	0.0006 (4)
N1	0.0268 (5)	0.0210 (5)	0.0336 (6)	0.0034 (4)	−0.0010 (4)	−0.0004 (4)
N2	0.0215 (5)	0.0200 (5)	0.0314 (5)	0.0030 (4)	−0.0008 (4)	0.0000 (4)
C1	0.0396 (7)	0.0221 (6)	0.0238 (6)	0.0032 (5)	0.0016 (5)	0.0015 (4)
C2	0.0229 (6)	0.0235 (6)	0.0431 (7)	0.0027 (5)	−0.0002 (5)	−0.0042 (5)
C3	0.0257 (6)	0.0229 (6)	0.0415 (7)	0.0045 (5)	−0.0071 (5)	0.0006 (5)
C4	0.0226 (6)	0.0232 (6)	0.0323 (6)	0.0048 (5)	−0.0021 (5)	0.0008 (5)
C5	0.0281 (6)	0.0233 (6)	0.0348 (6)	0.0034 (5)	−0.0045 (5)	0.0023 (5)
C6	0.0259 (6)	0.0209 (6)	0.0239 (6)	0.0026 (4)	−0.0028 (4)	−0.0013 (4)
C7	0.0286 (6)	0.0249 (6)	0.0294 (6)	0.0048 (5)	0.0037 (5)	−0.0004 (5)
C8	0.0363 (7)	0.0226 (6)	0.0290 (6)	0.0077 (5)	0.0023 (5)	−0.0015 (5)
C9	0.0383 (7)	0.0204 (6)	0.0233 (6)	−0.0009 (5)	−0.0023 (5)	−0.0011 (4)
C10	0.0274 (6)	0.0299 (7)	0.0371 (7)	−0.0019 (5)	0.0024 (5)	0.0008 (5)
C11	0.0246 (6)	0.0235 (6)	0.0386 (7)	0.0041 (5)	0.0013 (5)	−0.0006 (5)
C12	0.0500 (8)	0.0229 (6)	0.0354 (7)	−0.0018 (6)	−0.0080 (6)	−0.0012 (5)

O1—C1	1.2387 (16)	C4—C5	1.5200 (17)
O2—H2	0.8200	C5—H5A	0.9700
O2—C9	1.3681 (15)	C5—H5B	0.9700
N1—C1	1.3391 (16)	C6—C7	1.3950 (17)
N1—C2	1.4618 (15)	C6—C11	1.3943 (18)
N1—C5	1.4651 (16)	C7—H7	0.9300
N2—C3	1.4688 (15)	C7—C8	1.3875 (18)
N2—C4	1.4607 (14)	C8—H8	0.9300
N2—C6	1.4284 (15)	C8—C9	1.3888 (19)
C1—C12	1.5096 (18)	C9—C10	1.3869 (18)
C2—H2A	0.9700	C10—H10	0.9300
C2—H2B	0.9700	C10—C11	1.3896 (18)
C2—C3	1.5136 (18)	C11—H11	0.9300
C3—H3A	0.9700	C12—H12A	0.9600
C3—H3B	0.9700	C12—H12B	0.9600
C4—H4A	0.9700	C12—H12C	0.9600
C4—H4B	0.9700
C9—O2—H2	109.5	N1—C5—H5A	109.5
C1—N1—C2	124.54 (11)	N1—C5—H5B	109.5
C1—N1—C5	121.83 (10)	C4—C5—H5A	109.5
C2—N1—C5	113.35 (10)	C4—C5—H5B	109.5
C4—N2—C3	109.27 (9)	H5A—C5—H5B	108.0
C6—N2—C3	113.18 (9)	C7—C6—N2	118.97 (11)
C6—N2—C4	115.97 (9)	C11—C6—N2	123.30 (10)
O1—C1—N1	121.45 (13)	C11—C6—C7	117.74 (11)
O1—C1—C12	120.76 (12)	C6—C7—H7	119.5
N1—C1—C12	117.78 (11)	C8—C7—C6	120.95 (12)
N1—C2—H2A	109.6	C8—C7—H7	119.5
N1—C2—H2B	109.6	C7—C8—H8	119.6
N1—C2—C3	110.09 (10)	C7—C8—C9	120.83 (11)
H2A—C2—H2B	108.2	C9—C8—H8	119.6
C3—C2—H2A	109.6	O2—C9—C8	122.96 (11)
C3—C2—H2B	109.6	O2—C9—C10	118.35 (12)
N2—C3—C2	110.98 (10)	C10—C9—C8	118.68 (11)
N2—C3—H3A	109.4	C9—C10—H10	119.8
N2—C3—H3B	109.4	C9—C10—C11	120.45 (12)
C2—C3—H3A	109.4	C11—C10—H10	119.8
C2—C3—H3B	109.4	C6—C11—H11	119.3
H3A—C3—H3B	108.0	C10—C11—C6	121.31 (11)
N2—C4—H4A	109.7	C10—C11—H11	119.3
N2—C4—H4B	109.7	C1—C12—H12A	109.5
N2—C4—C5	109.99 (10)	C1—C12—H12B	109.5
H4A—C4—H4B	108.2	C1—C12—H12C	109.5
C5—C4—H4A	109.7	H12A—C12—H12B	109.5
C5—C4—H4B	109.7	H12A—C12—H12C	109.5
N1—C5—C4	110.90 (10)	H12B—C12—H12C	109.5
O2—C9—C10—C11	−179.37 (11)	C4—N2—C6—C7	−166.26 (11)
N1—C2—C3—N2	−56.20 (14)	C4—N2—C6—C11	14.00 (16)
N2—C4—C5—N1	56.23 (13)	C5—N1—C1—O1	−4.88 (19)
N2—C6—C7—C8	−179.02 (11)	C5—N1—C1—C12	174.25 (11)
N2—C6—C11—C10	−179.29 (11)	C5—N1—C2—C3	52.56 (14)
C1—N1—C2—C3	−133.46 (13)	C6—N2—C3—C2	−168.28 (10)
C1—N1—C5—C4	132.86 (12)	C6—N2—C4—C5	170.42 (10)
C2—N1—C1—O1	−178.37 (12)	C6—C7—C8—C9	−2.28 (19)
C2—N1—C1—C12	0.76 (18)	C7—C6—C11—C10	0.97 (19)
C2—N1—C5—C4	−52.98 (14)	C7—C8—C9—O2	−178.98 (11)
C3—N2—C4—C5	−60.23 (13)	C7—C8—C9—C10	2.06 (19)
C3—N2—C6—C7	66.31 (14)	C8—C9—C10—C11	−0.36 (19)
C3—N2—C6—C11	−113.43 (13)	C9—C10—C11—C6	−1.2 (2)
C4—N2—C3—C2	60.86 (13)	C11—C6—C7—C8	0.74 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.88	2.6953 (14)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.88	2.6953 (14)	170

Symmetry code: (i) .