2,2,2-Tris(pyrazol-1-yl)ethanol.

The title compound TPE, C(11)H(12)N(6)O, was prepared by slow evaporation from diethyl ether. In the crystal, there is a hydrogen bond between the alcohol H atom and an N in the pyrazole ring of a neighboring mol-ecule.

Related literature

For the original preparation, see: Reger et al. (2000 ▶). The title compound was prepared as part of our efforts to study tridentate scorpionate and psuedo-scorpionate ligands for coordination to vanadium, see: McLauchlan et al. (2004 ▶, 2009 ▶); McLauchlan & McDonald (2005 ▶, 2006 ▶). For coordination complexes with TPE, see: Sánchez-Méndez et al. (2004 ▶), Garcia-Orozco et al. (2006 ▶); Silva et al. (2009 ▶). For applications following substitution of the alcohol, see: Reger, Wright et al. (2001 ▶); Reger, Semeniuc et al. (2001 ▶); Reger & Grattan (2003 ▶); Pettinari & Pettinari (2005 ▶); Silva et al. (2009 ▶).

Experimental

Crystal data

C11H12N6O

M = 244.27

Monoclinic,

a = 19.6589 (14) Å

b = 11.5155 (8) Å

c = 12.4185 (18) Å

β = 125.740 (1)°

V = 2281.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 93 K

0.40 × 0.39 × 0.33 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.699, T max = 0.746

9505 measured reflections

2334 independent reflections

2187 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 1.05

2334 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012931/dn2673sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012931/dn2673Isup2.hkl

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

C11H12N6O	F(000) = 1024
Mr = 244.27	Dx = 1.422 Mg m−3
Monoclinic, C2/c	Melting point: 387(2) K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 19.6589 (14) Å	Cell parameters from 6831 reflections
b = 11.5155 (8) Å	θ = 2.2–31.4°
c = 12.4185 (18) Å	µ = 0.10 mm−1
β = 125.740 (1)°	T = 93 K
V = 2281.9 (4) Å3	Block, colorless
Z = 8	0.40 × 0.39 × 0.33 mm

Bruker SMART APEX CCD diffractometer	2334 independent reflections
Radiation source: fine-focus sealed tube	2187 reflections with I > 2σ(I)
graphite	Rint = 0.018
ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −24→23
Tmin = 0.699, Tmax = 0.746	k = −14→14
9505 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0454P)2 + 1.8611P] where P = (Fo2 + 2Fc2)/3
2334 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 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. H atoms for the pyrazoles and the methylene unit were modeled in fixed positions whereas the alcoholic H (on O1) was allowed to refine freely.

	x	y	z	Uiso*/Ueq
O1	0.16215 (5)	0.93915 (7)	0.05201 (8)	0.01904 (19)
N1	0.14888 (6)	1.06979 (8)	0.22818 (9)	0.0163 (2)
N2	0.18638 (6)	0.87863 (8)	0.30788 (9)	0.0161 (2)
N3	0.29052 (6)	1.02830 (8)	0.40204 (9)	0.0169 (2)
N4	0.16341 (6)	1.17862 (8)	0.20317 (10)	0.0198 (2)
N5	0.17186 (6)	0.88180 (8)	0.40312 (9)	0.0207 (2)
N6	0.36644 (6)	0.98761 (9)	0.43963 (10)	0.0225 (2)
C1	0.08823 (7)	1.22859 (10)	0.13521 (11)	0.0196 (2)
H1A	0.0782	1.3066	0.1046	0.024*
C2	0.02568 (7)	1.15312 (10)	0.11394 (11)	0.0214 (2)
H2A	−0.0324	1.1691	0.0684	0.026*
C3	0.06644 (7)	1.05131 (10)	0.17310 (11)	0.0198 (2)
H3A	0.0418	0.9812	0.1753	0.024*
C4	0.13735 (8)	0.77969 (10)	0.39302 (12)	0.0231 (3)
H4A	0.1210	0.7557	0.4480	0.028*
C5	0.12786 (7)	0.71147 (10)	0.29158 (12)	0.0221 (2)
H5A	0.1045	0.6358	0.2652	0.027*
C6	0.15956 (7)	0.77737 (9)	0.23876 (11)	0.0180 (2)
H6A	0.1623	0.7563	0.1674	0.022*
C7	0.42096 (8)	1.04416 (11)	0.55168 (12)	0.0242 (3)
H7A	0.4800	1.0341	0.6022	0.029*
C8	0.38124 (8)	1.12033 (10)	0.58653 (11)	0.0231 (3)
H8A	0.4068	1.1699	0.6617	0.028*
C9	0.29742 (7)	1.10762 (10)	0.48837 (11)	0.0199 (2)
H9A	0.2527	1.1469	0.4821	0.024*
C10	0.21515 (7)	0.98322 (9)	0.28018 (10)	0.0156 (2)
C11	0.23604 (7)	0.95939 (10)	0.17984 (10)	0.0168 (2)
H11A	0.2662	1.0269	0.1771	0.020*
H11B	0.2732	0.8908	0.2089	0.020*
H1O	0.1605 (10)	0.9921 (15)	0.0027 (17)	0.033 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0198 (4)	0.0210 (4)	0.0151 (4)	−0.0026 (3)	0.0094 (3)	0.0001 (3)
N1	0.0177 (5)	0.0141 (4)	0.0187 (5)	−0.0005 (3)	0.0116 (4)	−0.0007 (3)
N2	0.0192 (5)	0.0152 (4)	0.0161 (4)	0.0000 (3)	0.0115 (4)	−0.0003 (3)
N3	0.0167 (5)	0.0166 (4)	0.0171 (5)	−0.0006 (3)	0.0096 (4)	−0.0015 (4)
N4	0.0228 (5)	0.0154 (5)	0.0249 (5)	0.0002 (4)	0.0160 (4)	0.0017 (4)
N5	0.0278 (5)	0.0207 (5)	0.0192 (5)	−0.0005 (4)	0.0169 (4)	0.0002 (4)
N6	0.0168 (5)	0.0238 (5)	0.0220 (5)	0.0014 (4)	0.0087 (4)	−0.0031 (4)
C1	0.0235 (6)	0.0177 (5)	0.0190 (5)	0.0032 (4)	0.0132 (5)	0.0008 (4)
C2	0.0176 (5)	0.0227 (6)	0.0208 (6)	0.0010 (4)	0.0095 (5)	−0.0018 (4)
C3	0.0175 (5)	0.0199 (5)	0.0215 (5)	−0.0029 (4)	0.0111 (5)	−0.0029 (4)
C4	0.0292 (6)	0.0211 (6)	0.0255 (6)	−0.0015 (5)	0.0196 (5)	0.0024 (4)
C5	0.0246 (6)	0.0168 (5)	0.0266 (6)	−0.0023 (4)	0.0159 (5)	−0.0010 (4)
C6	0.0189 (5)	0.0157 (5)	0.0187 (5)	0.0000 (4)	0.0106 (5)	−0.0019 (4)
C7	0.0197 (6)	0.0265 (6)	0.0203 (6)	−0.0025 (5)	0.0081 (5)	−0.0023 (5)
C8	0.0267 (6)	0.0234 (6)	0.0184 (6)	−0.0069 (5)	0.0128 (5)	−0.0045 (4)
C9	0.0254 (6)	0.0189 (5)	0.0205 (5)	−0.0032 (4)	0.0163 (5)	−0.0031 (4)
C10	0.0158 (5)	0.0147 (5)	0.0162 (5)	−0.0004 (4)	0.0093 (4)	−0.0010 (4)
C11	0.0166 (5)	0.0188 (5)	0.0161 (5)	−0.0012 (4)	0.0102 (4)	−0.0009 (4)

O1—C11	1.4108 (13)	C2—C3	1.3669 (17)
O1—H1O	0.851 (18)	C2—H2A	0.9500
N1—C3	1.3582 (14)	C3—H3A	0.9500
N1—N4	1.3610 (13)	C4—C5	1.4015 (17)
N1—C10	1.4578 (13)	C4—H4A	0.9500
N2—C6	1.3586 (14)	C5—C6	1.3683 (16)
N2—N5	1.3698 (13)	C5—H5A	0.9500
N2—C10	1.4546 (14)	C6—H6A	0.9500
N3—C9	1.3535 (14)	C7—C8	1.4005 (18)
N3—N6	1.3607 (13)	C7—H7A	0.9500
N3—C10	1.4613 (14)	C8—C9	1.3696 (17)
N4—C1	1.3307 (15)	C8—H8A	0.9500
N5—C4	1.3263 (15)	C9—H9A	0.9500
N6—C7	1.3292 (16)	C10—C11	1.5475 (15)
C1—C2	1.3992 (16)	C11—H11A	0.9900
C1—H1A	0.9500	C11—H11B	0.9900
C11—O1—H1O	105.9 (11)	C6—C5—H5A	127.4
C3—N1—N4	112.15 (9)	C4—C5—H5A	127.4
C3—N1—C10	127.64 (9)	N2—C6—C5	106.90 (10)
N4—N1—C10	118.58 (9)	N2—C6—H6A	126.6
C6—N2—N5	111.62 (9)	C5—C6—H6A	126.6
C6—N2—C10	128.49 (9)	N6—C7—C8	112.10 (11)
N5—N2—C10	119.22 (9)	N6—C7—H7A	124.0
C9—N3—N6	112.23 (9)	C8—C7—H7A	124.0
C9—N3—C10	129.19 (9)	C9—C8—C7	104.84 (10)
N6—N3—C10	118.58 (9)	C9—C8—H8A	127.6
C1—N4—N1	103.86 (9)	C7—C8—H8A	127.6
C4—N5—N2	104.35 (9)	N3—C9—C8	106.80 (10)
C7—N6—N3	104.04 (9)	N3—C9—H9A	126.6
N4—C1—C2	112.28 (10)	C8—C9—H9A	126.6
N4—C1—H1A	123.9	N2—C10—N1	107.50 (8)
C2—C1—H1A	123.9	N2—C10—N3	110.38 (9)
C3—C2—C1	104.87 (10)	N1—C10—N3	108.60 (8)
C3—C2—H2A	127.6	N2—C10—C11	111.49 (8)
C1—C2—H2A	127.6	N1—C10—C11	110.70 (9)
N1—C3—C2	106.78 (10)	N3—C10—C11	108.15 (9)
N1—C3—H3A	126.6	O1—C11—C10	110.62 (9)
C2—C3—H3A	126.6	O1—C11—H11A	109.5
N5—C4—C5	111.97 (10)	C10—C11—H11A	109.5
N5—C4—H4A	124.0	O1—C11—H11B	109.5
C5—C4—H4A	124.0	C10—C11—H11B	109.5
C6—C5—C4	105.14 (10)	H11A—C11—H11B	108.1
C3—N1—N4—C1	2.18 (12)	C6—N2—C10—N1	105.80 (12)
C10—N1—N4—C1	168.76 (9)	N5—N2—C10—N1	−63.96 (12)
C6—N2—N5—C4	1.32 (12)	C6—N2—C10—N3	−135.91 (11)
C10—N2—N5—C4	172.70 (9)	N5—N2—C10—N3	54.33 (12)
C9—N3—N6—C7	−0.22 (13)	C6—N2—C10—C11	−15.69 (15)
C10—N3—N6—C7	−179.92 (10)	N5—N2—C10—C11	174.56 (9)
N1—N4—C1—C2	−1.23 (12)	C3—N1—C10—N2	−20.24 (14)
N4—C1—C2—C3	−0.10 (13)	N4—N1—C10—N2	175.52 (9)
N4—N1—C3—C2	−2.31 (13)	C3—N1—C10—N3	−139.67 (11)
C10—N1—C3—C2	−167.39 (10)	N4—N1—C10—N3	56.09 (12)
C1—C2—C3—N1	1.41 (12)	C3—N1—C10—C11	101.74 (12)
N2—N5—C4—C5	−1.10 (13)	N4—N1—C10—C11	−62.50 (12)
N5—C4—C5—C6	0.51 (14)	C9—N3—C10—N2	−91.92 (13)
N5—N2—C6—C5	−1.04 (12)	N6—N3—C10—N2	87.72 (11)
C10—N2—C6—C5	−171.42 (10)	C9—N3—C10—N1	25.69 (15)
C4—C5—C6—N2	0.32 (13)	N6—N3—C10—N1	−154.67 (9)
N3—N6—C7—C8	0.03 (14)	C9—N3—C10—C11	145.87 (11)
N6—C7—C8—C9	0.15 (14)	N6—N3—C10—C11	−34.49 (13)
N6—N3—C9—C8	0.32 (13)	N2—C10—C11—O1	70.77 (11)
C10—N3—C9—C8	179.98 (10)	N1—C10—C11—O1	−48.84 (12)
C7—C8—C9—N3	−0.28 (13)	N3—C10—C11—O1	−167.70 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N5i	0.851 (18)	2.003 (18)	2.8494 (13)	172.9 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N5i	0.851 (18)	2.003 (18)	2.8494 (13)	172.9 (16)

Symmetry code: (i) .