1,1'-(Piperazine-1,4-di-yl)dipropan-2-ol.

The asymmetric unit of the crystal contains one-fourth of the title compound, C(10)H(22)N(2)O(2), with the centre of the piperazine ring located at a site of 2/m symmetry. The piperazine ring adopts a chair conformation. The methine and methylene C atoms of the 2-hydroxypropyl groups show symmetry-imposed disorder over two equally occupied and mutually exclusive sets of positions. Only intra-molecular O-H⋯N contacts are observed.

Related literature

For the biological properties of piperazine compounds, see: Foroumadi et al. (2007 ▶); Upadhayaya et al. (2004 ▶); Chen et al. (2006 ▶); Cunico et al. (2009 ▶); Smits et al. (2008 ▶); Penjišević et al. (2007 ▶); Becker et al. (2006 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C10H22N2O2

M = 202.30

Monoclinic,

a = 13.838 (10) Å

b = 7.791 (5) Å

c = 5.543 (4) Å

β = 97.26 (3)°

V = 592.8 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 273 K

0.40 × 0.25 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

2493 measured reflections

604 independent reflections

441 reflections with I > 2σ(I)

R int = 0.139

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.119

S = 1.05

604 reflections

46 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.34 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023397/fy2011sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023397/fy2011Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023397/fy2011Isup3.cml

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

C10H22N2O2	F(000) = 224
Mr = 202.30	Dx = 1.133 Mg m−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 3092 reflections
a = 13.838 (10) Å	θ = 3.0–30.0°
b = 7.791 (5) Å	µ = 0.08 mm−1
c = 5.543 (4) Å	T = 273 K
β = 97.26 (3)°	Prism, colourless
V = 592.8 (7) Å3	0.40 × 0.25 × 0.10 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	441 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.139
graphite	θmax = 25.5°, θmin = 3.0°
Detector resolution: 10.00 pixels mm-1	h = −16→16
ω scans	k = −9→9
2493 measured reflections	l = −5→6
604 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.2898P] where P = (Fo2 + 2Fc2)/3
604 reflections	(Δ/σ)max < 0.001
46 parameters	Δρmax = 0.28 e Å−3
14 restraints	Δρmin = −0.34 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	Occ. (<1)
O1	0.78313 (12)	0.5000	0.4674 (3)	0.0706 (7)
H1	0.7297	0.5197	0.3907	0.106*	0.50
N1	0.60084 (15)	0.5000	0.5912 (4)	0.0715 (7)
C1	0.86326 (18)	0.5000	0.8733 (5)	0.0754 (9)
H1A	0.9169	0.4390	0.8197	0.113*	0.50
H1B	0.8573	0.4690	1.0384	0.113*	0.50
H1C	0.8746	0.6213	0.8640	0.113*	0.50
C2	0.7712 (2)	0.4545 (5)	0.7137 (5)	0.0603 (12)	0.50
H2	0.7597	0.3307	0.7233	0.072*	0.50
C3	0.6841 (2)	0.5495 (5)	0.7803 (6)	0.0609 (11)	0.50
H3A	0.6952	0.6724	0.7782	0.073*	0.50
H3B	0.6705	0.5166	0.9413	0.073*	0.50
C4	0.54111 (14)	0.6506 (3)	0.6021 (3)	0.0751 (7)
H4A	0.5806	0.7526	0.5917	0.090*
H4B	0.5150	0.6533	0.7565	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.0609 (11)	0.0975 (15)	0.0541 (11)	0.000	0.0103 (8)	0.000
N1	0.0463 (11)	0.118 (2)	0.0498 (12)	0.000	0.0031 (9)	0.000
C1	0.0527 (15)	0.103 (2)	0.0677 (17)	0.000	−0.0030 (13)	0.000
C2	0.0519 (15)	0.075 (3)	0.0533 (16)	0.0024 (15)	0.0027 (13)	−0.0010 (15)
C3	0.0483 (14)	0.084 (3)	0.0490 (14)	0.0021 (14)	0.0016 (12)	−0.0047 (14)
C4	0.0807 (13)	0.0883 (15)	0.0563 (11)	−0.0195 (11)	0.0084 (9)	−0.0038 (11)

O1—C2i	1.440 (4)	C1—H1B	0.9600
O1—C2	1.440 (4)	C1—H1C	0.9600
O1—H1	0.8200	C2—C3	1.499 (4)
N1—C4i	1.441 (3)	C2—H2	0.9800
N1—C4	1.441 (3)	C3—H3A	0.9700
N1—C3	1.507 (3)	C3—H3B	0.9700
N1—C3i	1.507 (3)	C4—C4ii	1.500 (4)
C1—C2	1.499 (4)	C4—H4A	0.9700
C1—C2i	1.499 (4)	C4—H4B	0.9700
C1—H1A	0.9600
C2i—O1—H1	103.9	O1—C2—C3	107.7 (2)
C2—O1—H1	109.5	C1—C2—C3	112.8 (3)
C4i—N1—C4	109.0 (2)	O1—C2—H2	109.4
C4i—N1—C3	124.8 (2)	C1—C2—H2	109.4
C4—N1—C3	98.90 (17)	C3—C2—H2	109.4
C4i—N1—C3i	98.90 (17)	C2—C3—N1	105.7 (2)
C4—N1—C3i	124.8 (2)	C2—C3—H3A	110.6
C2—C1—H1A	109.5	N1—C3—H3A	110.6
C2i—C1—H1A	124.6	C2—C3—H3B	110.6
C2—C1—H1B	109.5	N1—C3—H3B	110.6
C2i—C1—H1B	116.9	H3A—C3—H3B	108.7
H1A—C1—H1B	109.5	N1—C4—C4ii	110.64 (15)
C2—C1—H1C	109.5	N1—C4—H4A	109.5
C2i—C1—H1C	82.4	C4ii—C4—H4A	109.5
H1A—C1—H1C	109.5	N1—C4—H4B	109.5
H1B—C1—H1C	109.5	C4ii—C4—H4B	109.5
O1—C2—C1	108.1 (2)	H4A—C4—H4B	108.1
C2i—O1—C2—C1	−70.1 (2)	C4i—N1—C3—C2	85.4 (3)
C2i—O1—C2—C3	52.0 (2)	C4—N1—C3—C2	−153.8 (2)
C2i—C1—C2—O1	69.7 (2)	C3i—N1—C3—C2	52.8 (3)
C2i—C1—C2—C3	−49.2 (3)	C4i—N1—C4—C4ii	−58.1 (3)
O1—C2—C3—N1	56.3 (3)	C3—N1—C4—C4ii	170.2 (2)
C1—C2—C3—N1	175.4 (2)	C3i—N1—C4—C4ii	−174.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	2.22	2.696 (3)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	2.22	2.696 (3)	117