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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o186.
Published online 2009 December 19. doi:  10.1107/S1600536809053641
PMCID: PMC2980223

1-(4-Chloro­phen­yl)-1H-pyrazol-3-ol

Abstract

In the title compound, C9H7ClN2O, 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 [triangle]). For background to herbicides and plant-growth promoters related to the title compound, see: Shi et al. (1995 [triangle]); Xu et al. (2002 [triangle]).

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Object name is e-66-0o186-scheme1.jpg

Experimental

Crystal data

  • C9H7ClN2O
  • M r = 194.62
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o186-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL .

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The author thanks for the Scientific and Technological Foundation of Weifang Vacational College (No. WZKJ200907).

supplementary crystallographic information

Comment

p-Chlorophenyl hydrazine hydrochloride is an important biologically active compound used in herbicides and plant growth substances (Shi et al.,1995; Xu, et al.,2002). Here we report the crystal structure of the title compound (I).

In the title compound (I) (Fig. 1), the The dihedral angle between the pheny ring (C4,C5,C6,C7,C8 and C9) and ring 1(N1,N2,C1,C2 and C3) is 11.0 (2)°. The C—N bonds length in the range of (1.321 (5) Å-1.416 (5) Å) are in agreement with that observed before (Jian et al., 2005).

Experimental

A mixture of p-Chlorophenylhydrazing hydrochloride (0.02 mol) and methyl acrylate (0.02 mol) was stirred in ethanol (30 ml) at 353 K for 2 h to afford the title compound (yield 50%). Colourless bars of (I) were obtained by recrystallization from acetone at room temperature.

Refinement

The O-bound H atom was located in a difference map and freely refined. The C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C9H7ClN2OF(000) = 400
Mr = 194.62Dx = 1.494 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1171 reflections
a = 9.6461 (19) Åθ = 3.5–27.5°
b = 13.833 (3) ŵ = 0.40 mm1
c = 6.5045 (13) ÅT = 293 K
β = 94.33 (3)°Bar, colourless
V = 865.4 (3) Å30.11 × 0.09 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer1171 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 24.5°, θmin = 3.5°
ω scansh = −11→11
5771 measured reflectionsk = −16→16
1357 independent reflectionsl = −7→7

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146w = 1/[σ2(Fo2) + (0.0166P)2 + 1.7755P] where P = (Fo2 + 2Fc2)/3
S = 1.24(Δ/σ)max < 0.001
1357 reflectionsΔρmax = 0.23 e Å3
122 parametersΔρmin = −0.32 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.049 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl11.03021 (14)0.13637 (11)−0.3127 (2)0.0771 (6)
O10.3291 (3)0.0636 (2)0.5246 (5)0.0508 (8)
H10.377 (5)0.019 (3)0.588 (7)0.061*
N10.5047 (3)0.1156 (2)0.1005 (5)0.0361 (8)
N20.5009 (3)0.0759 (2)0.2928 (5)0.0380 (8)
C10.3807 (4)0.1554 (3)0.0396 (7)0.0458 (10)
H1A0.35880.1868−0.08510.055*
C20.2936 (4)0.1420 (3)0.1900 (6)0.0443 (10)
H2B0.20150.16170.19080.053*
C30.3726 (4)0.0919 (3)0.3442 (6)0.0386 (9)
C40.6308 (4)0.1525 (3)−0.1997 (6)0.0423 (10)
H4A0.54760.1707−0.27100.051*
C50.7541 (5)0.1583 (3)−0.2943 (6)0.0467 (11)
H5A0.75390.1807−0.42920.056*
C60.8760 (5)0.1314 (3)−0.1905 (7)0.0475 (11)
C70.8777 (4)0.0988 (3)0.0093 (7)0.0489 (11)
H7A0.96130.08080.07920.059*
C80.7556 (4)0.0929 (3)0.1066 (6)0.0414 (10)
H8A0.75700.07100.24190.050*
C90.6311 (4)0.1195 (2)0.0022 (6)0.0339 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0584 (9)0.1009 (11)0.0757 (10)−0.0004 (7)0.0298 (7)0.0190 (7)
O10.0422 (17)0.065 (2)0.0469 (18)0.0123 (14)0.0141 (15)0.0138 (14)
N10.0355 (18)0.0400 (17)0.0322 (17)0.0012 (13)−0.0011 (15)0.0040 (13)
N20.0361 (19)0.0440 (18)0.0338 (18)0.0036 (13)0.0011 (15)0.0065 (14)
C10.044 (2)0.051 (2)0.040 (2)0.0064 (18)−0.009 (2)0.0060 (18)
C20.034 (2)0.051 (2)0.048 (3)0.0073 (17)0.000 (2)−0.0012 (18)
C30.036 (2)0.038 (2)0.042 (2)0.0023 (16)0.0044 (19)−0.0017 (16)
C40.045 (2)0.045 (2)0.035 (2)−0.0016 (17)−0.007 (2)0.0043 (16)
C50.058 (3)0.048 (2)0.035 (2)−0.0062 (19)0.007 (2)0.0046 (17)
C60.048 (3)0.045 (2)0.052 (3)−0.0038 (18)0.015 (2)0.0037 (19)
C70.039 (2)0.052 (2)0.055 (3)0.0012 (18)0.004 (2)0.008 (2)
C80.042 (2)0.047 (2)0.035 (2)0.0014 (17)0.0012 (19)0.0063 (17)
C90.039 (2)0.0323 (19)0.030 (2)−0.0027 (15)−0.0007 (17)−0.0013 (14)

Geometric parameters (Å, °)

Cl1—C61.740 (4)C4—C51.382 (6)
O1—C31.334 (5)C4—C91.390 (5)
O1—H10.86 (5)C4—H4A0.9300
N1—C11.349 (5)C5—C61.363 (6)
N1—N21.369 (4)C5—H5A0.9300
N1—C91.420 (5)C6—C71.374 (6)
N2—C31.325 (5)C7—C81.381 (6)
C1—C21.349 (6)C7—H7A0.9300
C1—H1A0.9300C8—C91.384 (5)
C2—C31.396 (5)C8—H8A0.9300
C2—H2B0.9300
C3—O1—H1116 (3)C9—C4—H4A120.0
C1—N1—N2110.4 (3)C6—C5—C4120.2 (4)
C1—N1—C9128.7 (3)C6—C5—H5A119.9
N2—N1—C9120.6 (3)C4—C5—H5A119.9
C3—N2—N1104.7 (3)C5—C6—C7120.4 (4)
N1—C1—C2108.5 (4)C5—C6—Cl1119.9 (3)
N1—C1—H1A125.7C7—C6—Cl1119.7 (4)
C2—C1—H1A125.7C6—C7—C8120.2 (4)
C1—C2—C3104.7 (4)C6—C7—H7A119.9
C1—C2—H2B127.7C8—C7—H7A119.9
C3—C2—H2B127.7C7—C8—C9119.9 (4)
N2—C3—O1122.3 (3)C7—C8—H8A120.1
N2—C3—C2111.8 (3)C9—C8—H8A120.1
O1—C3—C2125.9 (4)C8—C9—C4119.4 (4)
C5—C4—C9119.9 (4)C8—C9—N1120.8 (3)
C5—C4—H4A120.0C4—C9—N1119.8 (3)
C1—N1—N2—C30.5 (4)C5—C6—C7—C80.2 (6)
C9—N1—N2—C3174.5 (3)Cl1—C6—C7—C8−178.8 (3)
N2—N1—C1—C2−0.3 (4)C6—C7—C8—C90.2 (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—C80.1 (6)
N1—N2—C3—C2−0.6 (4)C5—C4—C9—N1178.6 (3)
C1—C2—C3—N20.4 (5)C1—N1—C9—C8165.9 (4)
C1—C2—C3—O1179.4 (4)N2—N1—C9—C8−6.9 (5)
C9—C4—C5—C60.3 (6)C1—N1—C9—C4−12.7 (6)
C4—C5—C6—C7−0.4 (6)N2—N1—C9—C4174.5 (3)
C4—C5—C6—Cl1178.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.86 (4)1.89 (4)2.744 (4)173 (4)

Symmetry codes: (i) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5279).

References

  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jian, F.-F., Bai, Z.-S., Li, K. & Xiao, H.-L. (2005). Acta Cryst. E61, o393–o395.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, Y. N., Lu, Y. C. & Fang, J. X. (1995). Chem. J. Chin. Univ.16, 1710-1713.
  • Xu, L. Z., Zhang, S. S., Li, H. J. & Jiao, K. (2002). Chem. Res. Chin. Univ 18, 284-286.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography