4-[Tris(1H-pyrazol-1-yl)meth-yl]phenol.

The title compound, C(16)H(14)N(6)O, was prepared by the condensation of 4-(trifluoro-meth-yl)phenol and sodium pyrazol-1-ide in a yield of 58%. The dihedral angles formed by the planes of the pyrazole rings are 50.7 (2), 71.2 (3) and 95.8 (2)°. The mol-ecules are associated into dimers by pairs of inter-molecular O-H⋯N hydrogen bonds involving the hy-droxy groups and pyrazole N atoms. In addition, π-π stacking between the phenol rings of these inversion-related dimers is observed, with a ring centroid-to-centroid distance of 3.9247 (10) Å.

Related literature

For the preparation and coordination chemistry of tris(pyrazol­yl)borates and tris­(pyrazol­yl)methanes, see: Trofimenko (1966 ▶, 1970 ▶, 1999 ▶); Pettinari & Pettinari (2005 ▶); Reger et al. (2000 ▶). For the chemistry of tris­(pyrazol­yl)methane derivatives, see: Humphrey et al. (1999 ▶). For similar structures, see: Liddle & Gardinier (2007 ▶).

Experimental

Crystal data

C16H14N6O

M = 306.33

Triclinic,

a = 8.5065 (17) Å

b = 8.6829 (17) Å

c = 10.815 (2) Å

α = 96.97 (3)°

β = 91.51 (2)°

γ = 109.40 (3)°

V = 746.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.30 × 0.28 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: Gaussian (XPREP in SHELXTL; Sheldrick, 2008 ▶) T min = 0.973, T max = 0.983

4225 measured reflections

2609 independent reflections

1975 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.099

S = 1.07

2609 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: XL in SHELXTL/PC (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and POV-RAY (Persistence of Vision Team, 2004 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043042/pk2340sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043042/pk2340Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043042/pk2340Isup3.cml

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

C16H14N6O	Z = 2
Mr = 306.33	F(000) = 320
Triclinic, P1	Dx = 1.364 Mg m−3
Hall symbol: -P 1	Melting point: 443 K
a = 8.5065 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6829 (17) Å	Cell parameters from 2208 reflections
c = 10.815 (2) Å	θ = 2.9–27.5°
α = 96.97 (3)°	µ = 0.09 mm−1
β = 91.51 (2)°	T = 153 K
γ = 109.40 (3)°	Block, colourless
V = 746.0 (3) Å3	0.30 × 0.28 × 0.20 mm

Nonius KappaCCD diffractometer	2609 independent reflections
Radiation source: fine-focus sealed tube	1975 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: gaussian (XPREP in SHELXTL; Sheldrick, 2008)	h = −10→10
Tmin = 0.973, Tmax = 0.983	k = −10→10
4225 measured reflections	l = −12→11

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.038P)2 + 0.1787P] where P = (Fo2 + 2Fc2)/3
2609 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.27 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
O1	1.00800 (16)	1.32161 (15)	0.03852 (13)	0.0266 (3)
H1A	0.9790	1.2970	−0.0362	0.054 (8)*
N1	0.74972 (17)	0.78542 (18)	0.40566 (13)	0.0180 (4)
N2	0.69159 (19)	0.65739 (19)	0.47332 (15)	0.0244 (4)
N3	0.98104 (17)	0.72693 (18)	0.31464 (14)	0.0181 (4)
N4	1.08607 (18)	0.73336 (19)	0.22092 (15)	0.0237 (4)
N5	0.70790 (17)	0.60541 (17)	0.21695 (14)	0.0173 (4)
N6	0.54566 (18)	0.59411 (18)	0.19620 (14)	0.0216 (4)
C1	0.9528 (2)	1.1846 (2)	0.09625 (17)	0.0197 (4)
C2	0.8251 (2)	1.0424 (2)	0.04486 (17)	0.0213 (4)
H2A	0.7695	1.0394	−0.0311	0.026*
C3	0.7802 (2)	0.9051 (2)	0.10623 (16)	0.0191 (4)
H3A	0.6944	0.8103	0.0711	0.023*
C4	0.8613 (2)	0.9069 (2)	0.21937 (16)	0.0165 (4)
C5	0.9873 (2)	1.0523 (2)	0.27129 (17)	0.0206 (4)
H5A	1.0427	1.0560	0.3475	0.025*
C6	1.0305 (2)	1.1896 (2)	0.21160 (17)	0.0213 (4)
H6A	1.1121	1.2863	0.2487	0.026*
C7	0.8240 (2)	0.7575 (2)	0.28833 (16)	0.0173 (4)
C8	0.6124 (2)	0.7133 (2)	0.56240 (18)	0.0250 (5)
H8A	0.5599	0.6528	0.6241	0.030*
C9	0.6169 (2)	0.8729 (2)	0.55301 (18)	0.0263 (5)
H9A	0.5710	0.9371	0.6055	0.032*
C10	0.7026 (2)	0.9154 (2)	0.45071 (17)	0.0208 (4)
H10A	0.7246	1.0141	0.4180	0.025*
C11	1.2086 (2)	0.6894 (2)	0.2675 (2)	0.0268 (5)
H11A	1.2999	0.6832	0.2244	0.032*
C12	1.1831 (2)	0.6538 (2)	0.3889 (2)	0.0281 (5)
H12A	1.2517	0.6210	0.4405	0.034*
C13	1.0367 (2)	0.6771 (2)	0.41634 (18)	0.0225 (5)
H13A	0.9846	0.6617	0.4906	0.027*
C14	0.4724 (2)	0.4422 (2)	0.13858 (17)	0.0220 (4)
H14A	0.3599	0.3985	0.1111	0.026*
C15	0.5835 (2)	0.3552 (2)	0.12394 (19)	0.0284 (5)
H15A	0.5602	0.2468	0.0870	0.034*
C16	0.7341 (2)	0.4636 (2)	0.17562 (18)	0.0238 (5)
H16A	0.8347	0.4434	0.1811	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0374 (8)	0.0219 (8)	0.0236 (9)	0.0116 (6)	0.0085 (6)	0.0092 (6)
N1	0.0197 (8)	0.0170 (8)	0.0171 (8)	0.0049 (7)	0.0029 (7)	0.0049 (7)
N2	0.0284 (9)	0.0226 (9)	0.0218 (9)	0.0056 (7)	0.0055 (7)	0.0093 (7)
N3	0.0155 (8)	0.0185 (9)	0.0209 (9)	0.0065 (6)	0.0013 (7)	0.0034 (7)
N4	0.0187 (8)	0.0256 (9)	0.0297 (10)	0.0101 (7)	0.0072 (7)	0.0066 (8)
N5	0.0149 (8)	0.0167 (9)	0.0207 (9)	0.0063 (6)	0.0007 (6)	0.0017 (7)
N6	0.0152 (8)	0.0231 (9)	0.0255 (9)	0.0057 (7)	0.0005 (7)	0.0023 (7)
C1	0.0231 (10)	0.0180 (11)	0.0234 (11)	0.0126 (8)	0.0098 (8)	0.0056 (8)
C2	0.0241 (10)	0.0261 (11)	0.0178 (10)	0.0133 (9)	0.0009 (8)	0.0044 (9)
C3	0.0184 (10)	0.0202 (11)	0.0183 (10)	0.0067 (8)	0.0003 (8)	0.0001 (8)
C4	0.0156 (9)	0.0167 (10)	0.0189 (10)	0.0077 (8)	0.0041 (8)	0.0025 (8)
C5	0.0181 (10)	0.0235 (11)	0.0199 (11)	0.0070 (8)	−0.0014 (8)	0.0020 (8)
C6	0.0210 (10)	0.0167 (10)	0.0235 (11)	0.0032 (8)	0.0030 (8)	0.0011 (8)
C7	0.0145 (9)	0.0186 (10)	0.0188 (10)	0.0061 (8)	0.0008 (8)	0.0017 (8)
C8	0.0210 (10)	0.0329 (12)	0.0185 (11)	0.0049 (9)	0.0037 (8)	0.0048 (9)
C9	0.0228 (11)	0.0321 (12)	0.0248 (11)	0.0120 (9)	0.0039 (9)	−0.0010 (9)
C10	0.0206 (10)	0.0201 (10)	0.0241 (11)	0.0106 (8)	−0.0002 (8)	0.0013 (8)
C11	0.0181 (10)	0.0227 (11)	0.0415 (14)	0.0090 (9)	0.0027 (9)	0.0056 (10)
C12	0.0228 (11)	0.0230 (11)	0.0400 (14)	0.0101 (9)	−0.0097 (9)	0.0057 (10)
C13	0.0255 (11)	0.0191 (11)	0.0223 (11)	0.0066 (8)	−0.0046 (8)	0.0046 (8)
C14	0.0190 (10)	0.0220 (11)	0.0199 (11)	0.0005 (8)	0.0004 (8)	0.0023 (8)
C15	0.0305 (12)	0.0193 (11)	0.0309 (12)	0.0053 (9)	0.0004 (9)	−0.0042 (9)
C16	0.0253 (11)	0.0198 (11)	0.0297 (12)	0.0128 (9)	0.0023 (9)	0.0012 (9)

O1—C1	1.360 (2)	C4—C5	1.399 (3)
O1—H1A	0.8200	C4—C7	1.521 (3)
N1—C10	1.360 (2)	C5—C6	1.371 (3)
N1—N2	1.366 (2)	C5—H5A	0.9300
N1—C7	1.462 (2)	C6—H6A	0.9300
N2—C8	1.325 (2)	C8—C9	1.390 (3)
N3—C13	1.358 (2)	C8—H8A	0.9300
N3—N4	1.363 (2)	C9—C10	1.362 (3)
N3—C7	1.473 (2)	C9—H9A	0.9300
N4—C11	1.330 (2)	C10—H10A	0.9300
N5—C16	1.349 (2)	C11—C12	1.391 (3)
N5—N6	1.361 (2)	C11—H11A	0.9300
N5—C7	1.470 (2)	C12—C13	1.361 (3)
N6—C14	1.323 (2)	C12—H12A	0.9300
C1—C6	1.385 (3)	C13—H13A	0.9300
C1—C2	1.387 (3)	C14—C15	1.393 (3)
C2—C3	1.382 (3)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.369 (3)
C3—C4	1.385 (2)	C15—H15A	0.9300
C3—H3A	0.9300	C16—H16A	0.9300
C1—O1—H1A	109.5	N1—C7—N3	109.47 (14)
C10—N1—N2	111.56 (15)	N5—C7—N3	107.01 (14)
C10—N1—C7	128.86 (15)	N1—C7—C4	110.73 (14)
N2—N1—C7	118.61 (14)	N5—C7—C4	113.65 (14)
C8—N2—N1	104.13 (15)	N3—C7—C4	108.88 (14)
C13—N3—N4	111.24 (14)	N2—C8—C9	112.15 (18)
C13—N3—C7	130.58 (16)	N2—C8—H8A	123.9
N4—N3—C7	117.89 (14)	C9—C8—H8A	123.9
C11—N4—N3	104.65 (15)	C10—C9—C8	105.46 (18)
C16—N5—N6	112.33 (15)	C10—C9—H9A	127.3
C16—N5—C7	129.11 (15)	C8—C9—H9A	127.3
N6—N5—C7	118.30 (14)	N1—C10—C9	106.65 (17)
C14—N6—N5	103.95 (14)	N1—C10—H10A	126.7
O1—C1—C6	117.37 (17)	C9—C10—H10A	126.7
O1—C1—C2	123.26 (17)	N4—C11—C12	111.55 (17)
C6—C1—C2	119.36 (17)	N4—C11—H11A	124.2
C3—C2—C1	120.19 (17)	C12—C11—H11A	124.2
C3—C2—H2A	119.9	C13—C12—C11	105.54 (17)
C1—C2—H2A	119.9	C13—C12—H12A	127.2
C2—C3—C4	120.83 (17)	C11—C12—H12A	127.2
C2—C3—H3A	119.6	N3—C13—C12	107.00 (18)
C4—C3—H3A	119.6	N3—C13—H13A	126.5
C3—C4—C5	118.31 (17)	C12—C13—H13A	126.5
C3—C4—C7	123.42 (16)	N6—C14—C15	112.14 (17)
C5—C4—C7	118.25 (16)	N6—C14—H14A	123.9
C6—C5—C4	121.01 (17)	C15—C14—H14A	123.9
C6—C5—H5A	119.5	C16—C15—C14	105.15 (17)
C4—C5—H5A	119.5	C16—C15—H15A	127.4
C5—C6—C1	120.22 (17)	C14—C15—H15A	127.4
C5—C6—H6A	119.9	N5—C16—C15	106.41 (17)
C1—C6—H6A	119.9	N5—C16—H16A	126.8
N1—C7—N5	106.98 (14)	C15—C16—H16A	126.8

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N4i	0.82	2.02	2.836 (2)	173.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N4i	0.82	2.02	2.836 (2)	173

Symmetry code: (i) .