1-(4-Chloro-phen-yl)-1H-pyrazol-3-ol.

In the title compound, C(9)H(7)ClN(2)O, the dihedral angle between the aromatic ring planes is 11.0 (2)°. In the crystal, inversion dimers linked by pairs of O-H⋯N hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For a related structure, see: Jian et al. (2005 ▶). For background to herbicides and plant-growth promoters related to the title compound, see: Shi et al. (1995 ▶); Xu et al. (2002 ▶).

Experimental

Crystal data

C9H7ClN2O

M = 194.62

Monoclinic,

a = 9.6461 (19) Å

b = 13.833 (3) Å

c = 6.5045 (13) Å

β = 94.33 (3)°

V = 865.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 293 K

0.11 × 0.09 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

5771 measured reflections

1357 independent reflections

1171 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.146

S = 1.24

1357 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL .

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053641/hb5279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053641/hb5279Isup2.hkl

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

C9H7ClN2O	F(000) = 400
Mr = 194.62	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1171 reflections
a = 9.6461 (19) Å	θ = 3.5–27.5°
b = 13.833 (3) Å	µ = 0.40 mm−1
c = 6.5045 (13) Å	T = 293 K
β = 94.33 (3)°	Bar, colourless
V = 865.4 (3) Å3	0.11 × 0.09 × 0.08 mm
Z = 4

Bruker SMART CCD diffractometer	1171 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
graphite	θmax = 24.5°, θmin = 3.5°
ω scans	h = −11→11
5771 measured reflections	k = −16→16
1357 independent reflections	l = −7→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.0166P)2 + 1.7755P] where P = (Fo2 + 2Fc2)/3
S = 1.24	(Δ/σ)max < 0.001
1357 reflections	Δρmax = 0.23 e Å−3
122 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (5)

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
Cl1	1.03021 (14)	0.13637 (11)	−0.3127 (2)	0.0771 (6)
O1	0.3291 (3)	0.0636 (2)	0.5246 (5)	0.0508 (8)
H1	0.377 (5)	0.019 (3)	0.588 (7)	0.061*
N1	0.5047 (3)	0.1156 (2)	0.1005 (5)	0.0361 (8)
N2	0.5009 (3)	0.0759 (2)	0.2928 (5)	0.0380 (8)
C1	0.3807 (4)	0.1554 (3)	0.0396 (7)	0.0458 (10)
H1A	0.3588	0.1868	−0.0851	0.055*
C2	0.2936 (4)	0.1420 (3)	0.1900 (6)	0.0443 (10)
H2B	0.2015	0.1617	0.1908	0.053*
C3	0.3726 (4)	0.0919 (3)	0.3442 (6)	0.0386 (9)
C4	0.6308 (4)	0.1525 (3)	−0.1997 (6)	0.0423 (10)
H4A	0.5476	0.1707	−0.2710	0.051*
C5	0.7541 (5)	0.1583 (3)	−0.2943 (6)	0.0467 (11)
H5A	0.7539	0.1807	−0.4292	0.056*
C6	0.8760 (5)	0.1314 (3)	−0.1905 (7)	0.0475 (11)
C7	0.8777 (4)	0.0988 (3)	0.0093 (7)	0.0489 (11)
H7A	0.9613	0.0808	0.0792	0.059*
C8	0.7556 (4)	0.0929 (3)	0.1066 (6)	0.0414 (10)
H8A	0.7570	0.0710	0.2419	0.050*
C9	0.6311 (4)	0.1195 (2)	0.0022 (6)	0.0339 (9)

	U11	U22	U33	U12	U13	U23
Cl1	0.0584 (9)	0.1009 (11)	0.0757 (10)	−0.0004 (7)	0.0298 (7)	0.0190 (7)
O1	0.0422 (17)	0.065 (2)	0.0469 (18)	0.0123 (14)	0.0141 (15)	0.0138 (14)
N1	0.0355 (18)	0.0400 (17)	0.0322 (17)	0.0012 (13)	−0.0011 (15)	0.0040 (13)
N2	0.0361 (19)	0.0440 (18)	0.0338 (18)	0.0036 (13)	0.0011 (15)	0.0065 (14)
C1	0.044 (2)	0.051 (2)	0.040 (2)	0.0064 (18)	−0.009 (2)	0.0060 (18)
C2	0.034 (2)	0.051 (2)	0.048 (3)	0.0073 (17)	0.000 (2)	−0.0012 (18)
C3	0.036 (2)	0.038 (2)	0.042 (2)	0.0023 (16)	0.0044 (19)	−0.0017 (16)
C4	0.045 (2)	0.045 (2)	0.035 (2)	−0.0016 (17)	−0.007 (2)	0.0043 (16)
C5	0.058 (3)	0.048 (2)	0.035 (2)	−0.0062 (19)	0.007 (2)	0.0046 (17)
C6	0.048 (3)	0.045 (2)	0.052 (3)	−0.0038 (18)	0.015 (2)	0.0037 (19)
C7	0.039 (2)	0.052 (2)	0.055 (3)	0.0012 (18)	0.004 (2)	0.008 (2)
C8	0.042 (2)	0.047 (2)	0.035 (2)	0.0014 (17)	0.0012 (19)	0.0063 (17)
C9	0.039 (2)	0.0323 (19)	0.030 (2)	−0.0027 (15)	−0.0007 (17)	−0.0013 (14)

Cl1—C6	1.740 (4)	C4—C5	1.382 (6)
O1—C3	1.334 (5)	C4—C9	1.390 (5)
O1—H1	0.86 (5)	C4—H4A	0.9300
N1—C1	1.349 (5)	C5—C6	1.363 (6)
N1—N2	1.369 (4)	C5—H5A	0.9300
N1—C9	1.420 (5)	C6—C7	1.374 (6)
N2—C3	1.325 (5)	C7—C8	1.381 (6)
C1—C2	1.349 (6)	C7—H7A	0.9300
C1—H1A	0.9300	C8—C9	1.384 (5)
C2—C3	1.396 (5)	C8—H8A	0.9300
C2—H2B	0.9300
C3—O1—H1	116 (3)	C9—C4—H4A	120.0
C1—N1—N2	110.4 (3)	C6—C5—C4	120.2 (4)
C1—N1—C9	128.7 (3)	C6—C5—H5A	119.9
N2—N1—C9	120.6 (3)	C4—C5—H5A	119.9
C3—N2—N1	104.7 (3)	C5—C6—C7	120.4 (4)
N1—C1—C2	108.5 (4)	C5—C6—Cl1	119.9 (3)
N1—C1—H1A	125.7	C7—C6—Cl1	119.7 (4)
C2—C1—H1A	125.7	C6—C7—C8	120.2 (4)
C1—C2—C3	104.7 (4)	C6—C7—H7A	119.9
C1—C2—H2B	127.7	C8—C7—H7A	119.9
C3—C2—H2B	127.7	C7—C8—C9	119.9 (4)
N2—C3—O1	122.3 (3)	C7—C8—H8A	120.1
N2—C3—C2	111.8 (3)	C9—C8—H8A	120.1
O1—C3—C2	125.9 (4)	C8—C9—C4	119.4 (4)
C5—C4—C9	119.9 (4)	C8—C9—N1	120.8 (3)
C5—C4—H4A	120.0	C4—C9—N1	119.8 (3)
C1—N1—N2—C3	0.5 (4)	C5—C6—C7—C8	0.2 (6)
C9—N1—N2—C3	174.5 (3)	Cl1—C6—C7—C8	−178.8 (3)
N2—N1—C1—C2	−0.3 (4)	C6—C7—C8—C9	0.2 (6)
C9—N1—C1—C2	−173.7 (3)	C7—C8—C9—C4	−0.3 (6)
N1—C1—C2—C3	−0.1 (5)	C7—C8—C9—N1	−178.9 (3)
N1—N2—C3—O1	−179.6 (3)	C5—C4—C9—C8	0.1 (6)
N1—N2—C3—C2	−0.6 (4)	C5—C4—C9—N1	178.6 (3)
C1—C2—C3—N2	0.4 (5)	C1—N1—C9—C8	165.9 (4)
C1—C2—C3—O1	179.4 (4)	N2—N1—C9—C8	−6.9 (5)
C9—C4—C5—C6	0.3 (6)	C1—N1—C9—C4	−12.7 (6)
C4—C5—C6—C7	−0.4 (6)	N2—N1—C9—C4	174.5 (3)
C4—C5—C6—Cl1	178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.86 (4)	1.89 (4)	2.744 (4)	173 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.86 (4)	1.89 (4)	2.744 (4)	173 (4)

Symmetry code: (i) .