Acta Cryst. (2010). E66, o186 [ doi:10.1107/S1600536809053641 ]
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 R22(8) loops.
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.
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.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).
![[Figure 1]](./hb5279fig1thm.gif)
| Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. |
| 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) |
| C9H7ClN2O | V = 865.4 (3) Å3 |
| Mr = 194.62 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.6461 (19) Å | µ = 0.40 mm−1 |
| b = 13.833 (3) Å | T = 293 K |
| c = 6.5045 (13) Å | 0.11 × 0.09 × 0.08 mm |
| β = 94.33 (3)° |
| Bruker SMART CCD diffractometer | 1171 reflections with I > 2σ(I) |
| 5771 measured reflections | Rint = 0.038 |
| 1357 independent reflections | θmax = 24.5° |
| R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.146 | Δρmax = 0.23 e Å−3 |
| S = 1.24 | Δρmin = −0.32 e Å−3 |
| 1357 reflections | Absolute structure: ? |
| 122 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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) |
| Symmetry codes: (i) −x+1, −y, −z+1. |
| 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 codes: (i) −x+1, −y, −z+1. |
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.
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.
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).