Acta Cryst. (2008). E64, o2134 [ doi:10.1107/S1600536808033217 ]
In the title compound, C7H5Cl2NO, there are two molecules in the asymmetric unit. The molecules are essentially identical. Each molecule is connected to a symmetry-related molecule through an inversion center by O-H
N hydrogen bonds, building an R22(6) graph-set motif.
2,6-dichlorobenzaldehyde (1 mmol) was dissolved in anhydrous methanol, hydroxylamine hydrochloride and sodium carbonate were added to this, the mixture was stirred for 3 h at room temperature. The product was isolated and recrystallized in dichloromethane, colourless single crystals of (I) was obtained after 5 d.
All H atoms were placed in calculated position and treated as riding on their parent atoms with C—H=0.93Å or O—H=0.82 Å with Uiso(H)=1.2Ueq(C) or 1.5Ueq(O) for the hydroxyl H atom.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./dn2391fig1thm.gif)
| Fig. 1. The asymmetric unit of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. |
![[Figure 2]](./dn2391fig2thm.gif)
| Fig. 2. Partial packing view of compound ( I ), showing the formation of dimer through R22(6) graph set motif. H bonds are represented as dashed lines. H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1 , -y+2, -z+1.] |
| C7H5Cl2NO | Z = 4 |
| Mr = 190.02 | F(000) = 384 |
| Triclinic, P1 | Dx = 1.610 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 3.8074 (1) Å | Cell parameters from 5529 reflections |
| b = 14.3712 (2) Å | θ = 2.8–27.4° |
| c = 14.3835 (3) Å | µ = 0.76 mm−1 |
| α = 89.108 (1)° | T = 296 K |
| β = 88.545 (1)° | Block, colourless |
| γ = 85.296 (1)° | 0.26 × 0.24 × 0.16 mm |
| V = 784.04 (3) Å3 |
| Bruker SMART CCD area-detector diffractometer | 3235 independent reflections |
| Radiation source: fine-focus sealed tube | 2809 reflections with I > 2σ(I) |
| graphite | Rint = 0.018 |
| ω scans | θmax = 26.5°, θmin = 1.4° |
| Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −4→4 |
| Tmin = 0.818, Tmax = 0.884 | k = −17→17 |
| 11107 measured reflections | l = −18→18 |
| 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.085 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0352P)2 + 0.3155P] where P = (Fo2 + 2Fc2)/3 |
| 3235 reflections | (Δ/σ)max = 0.001 |
| 201 parameters | Δρmax = 0.40 e Å−3 |
| 0 restraints | Δρmin = −0.31 e Å−3 |
| C7H5Cl2NO | γ = 85.296 (1)° |
| Mr = 190.02 | V = 784.04 (3) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 3.8074 (1) Å | Mo Kα radiation |
| b = 14.3712 (2) Å | µ = 0.76 mm−1 |
| c = 14.3835 (3) Å | T = 296 K |
| α = 89.108 (1)° | 0.26 × 0.24 × 0.16 mm |
| β = 88.545 (1)° |
| Bruker SMART CCD area-detector diffractometer | 3235 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2809 reflections with I > 2σ(I) |
| Tmin = 0.818, Tmax = 0.884 | Rint = 0.018 |
| 11107 measured reflections | θmax = 26.5° |
| R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
| wR(F2) = 0.085 | Δρmax = 0.40 e Å−3 |
| S = 1.06 | Δρmin = −0.31 e Å−3 |
| 3235 reflections | Absolute structure: ? |
| 201 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | 0.16981 (16) | 0.12516 (3) | 1.04669 (4) | 0.06328 (16) | |
| Cl2 | −0.28140 (15) | 0.39071 (3) | 0.79443 (4) | 0.05813 (16) | |
| N1 | −0.0849 (4) | 0.39836 (10) | 0.99884 (10) | 0.0430 (3) | |
| O1 | −0.2185 (4) | 0.44211 (9) | 1.07941 (9) | 0.0574 (4) | |
| H1 | −0.1779 | 0.4973 | 1.0774 | 0.086* | |
| C1 | −0.0441 (4) | 0.25470 (11) | 0.91699 (11) | 0.0371 (4) | |
| C2 | 0.1056 (5) | 0.16371 (12) | 0.93282 (13) | 0.0426 (4) | |
| C3 | 0.2132 (6) | 0.10360 (13) | 0.86200 (16) | 0.0551 (5) | |
| H3 | 0.3128 | 0.0437 | 0.8752 | 0.066* | |
| C4 | 0.1703 (7) | 0.13390 (15) | 0.77145 (16) | 0.0653 (6) | |
| H4 | 0.2431 | 0.0943 | 0.7229 | 0.078* | |
| C5 | 0.0202 (6) | 0.22243 (15) | 0.75209 (14) | 0.0599 (5) | |
| H5 | −0.0105 | 0.2422 | 0.6908 | 0.072* | |
| C6 | −0.0839 (5) | 0.28136 (12) | 0.82397 (13) | 0.0434 (4) | |
| C7 | −0.1573 (5) | 0.31429 (12) | 0.99624 (12) | 0.0416 (4) | |
| H7 | −0.2847 | 0.2895 | 1.0454 | 0.050* | |
| Cl3 | 0.60840 (16) | 0.62545 (3) | 0.44764 (4) | 0.06139 (16) | |
| Cl4 | 0.35612 (19) | 0.88605 (4) | 0.71520 (4) | 0.07117 (19) | |
| N2 | 0.4237 (4) | 0.89871 (10) | 0.50330 (10) | 0.0429 (3) | |
| O2 | 0.2629 (4) | 0.94385 (9) | 0.42708 (9) | 0.0538 (3) | |
| H2 | 0.3079 | 0.9987 | 0.4256 | 0.081* | |
| C8 | 0.5024 (4) | 0.75283 (11) | 0.58413 (11) | 0.0384 (4) | |
| C9 | 0.6303 (5) | 0.66160 (12) | 0.56212 (13) | 0.0421 (4) | |
| C10 | 0.7785 (5) | 0.59945 (13) | 0.62661 (16) | 0.0546 (5) | |
| H10 | 0.8605 | 0.5393 | 0.6093 | 0.065* | |
| C11 | 0.8035 (6) | 0.62748 (15) | 0.71651 (16) | 0.0618 (6) | |
| H11 | 0.9070 | 0.5864 | 0.7604 | 0.074* | |
| C12 | 0.6773 (6) | 0.71567 (15) | 0.74256 (14) | 0.0612 (6) | |
| H12 | 0.6931 | 0.7340 | 0.8039 | 0.073* | |
| C13 | 0.5265 (5) | 0.77725 (12) | 0.67727 (13) | 0.0477 (4) | |
| C14 | 0.3507 (5) | 0.81491 (11) | 0.51094 (12) | 0.0406 (4) | |
| H14 | 0.1973 | 0.7919 | 0.4693 | 0.049* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0848 (4) | 0.0441 (3) | 0.0602 (3) | 0.0013 (2) | −0.0151 (3) | 0.0096 (2) |
| Cl2 | 0.0817 (4) | 0.0398 (3) | 0.0525 (3) | 0.0009 (2) | −0.0155 (2) | 0.0047 (2) |
| N1 | 0.0565 (9) | 0.0348 (7) | 0.0375 (8) | −0.0012 (6) | −0.0006 (6) | −0.0057 (6) |
| O1 | 0.0891 (11) | 0.0393 (7) | 0.0429 (7) | −0.0001 (7) | 0.0089 (7) | −0.0099 (6) |
| C1 | 0.0395 (9) | 0.0296 (8) | 0.0428 (9) | −0.0062 (6) | −0.0018 (7) | −0.0032 (7) |
| C2 | 0.0440 (10) | 0.0329 (8) | 0.0514 (10) | −0.0052 (7) | −0.0040 (8) | −0.0010 (7) |
| C3 | 0.0587 (12) | 0.0330 (9) | 0.0729 (14) | 0.0009 (8) | 0.0011 (10) | −0.0095 (9) |
| C4 | 0.0859 (16) | 0.0477 (12) | 0.0617 (13) | −0.0014 (11) | 0.0098 (12) | −0.0206 (10) |
| C5 | 0.0861 (16) | 0.0497 (11) | 0.0445 (11) | −0.0080 (10) | 0.0018 (10) | −0.0081 (9) |
| C6 | 0.0516 (10) | 0.0331 (8) | 0.0462 (10) | −0.0065 (7) | −0.0038 (8) | −0.0026 (7) |
| C7 | 0.0480 (10) | 0.0349 (9) | 0.0417 (9) | −0.0035 (7) | 0.0023 (7) | 0.0002 (7) |
| Cl3 | 0.0811 (4) | 0.0450 (3) | 0.0574 (3) | 0.0006 (2) | 0.0000 (3) | −0.0139 (2) |
| Cl4 | 0.1140 (5) | 0.0476 (3) | 0.0511 (3) | −0.0031 (3) | 0.0111 (3) | −0.0128 (2) |
| N2 | 0.0526 (9) | 0.0351 (7) | 0.0403 (8) | −0.0002 (6) | −0.0031 (6) | 0.0031 (6) |
| O2 | 0.0744 (9) | 0.0380 (7) | 0.0486 (7) | 0.0001 (6) | −0.0127 (7) | 0.0071 (6) |
| C8 | 0.0419 (9) | 0.0317 (8) | 0.0422 (9) | −0.0069 (7) | 0.0001 (7) | 0.0022 (7) |
| C9 | 0.0444 (10) | 0.0337 (8) | 0.0488 (10) | −0.0068 (7) | −0.0008 (8) | −0.0002 (7) |
| C10 | 0.0569 (12) | 0.0343 (9) | 0.0728 (14) | −0.0048 (8) | −0.0082 (10) | 0.0080 (9) |
| C11 | 0.0744 (15) | 0.0481 (11) | 0.0644 (13) | −0.0124 (10) | −0.0206 (11) | 0.0208 (10) |
| C12 | 0.0871 (16) | 0.0552 (12) | 0.0443 (11) | −0.0219 (11) | −0.0113 (10) | 0.0082 (9) |
| C13 | 0.0630 (12) | 0.0371 (9) | 0.0441 (10) | −0.0105 (8) | 0.0017 (8) | −0.0001 (7) |
| C14 | 0.0451 (10) | 0.0346 (9) | 0.0422 (9) | −0.0027 (7) | −0.0020 (7) | −0.0020 (7) |
| Cl1—C2 | 1.7376 (19) | Cl3—C9 | 1.7403 (19) |
| Cl2—C6 | 1.7370 (18) | Cl4—C13 | 1.7336 (19) |
| N1—C7 | 1.262 (2) | N2—C14 | 1.261 (2) |
| N1—O1 | 1.3919 (19) | N2—O2 | 1.3945 (18) |
| O1—H1 | 0.8200 | O2—H2 | 0.8200 |
| C1—C6 | 1.394 (2) | C8—C13 | 1.397 (2) |
| C1—C2 | 1.401 (2) | C8—C9 | 1.399 (2) |
| C1—C7 | 1.471 (2) | C8—C14 | 1.468 (2) |
| C2—C3 | 1.378 (3) | C9—C10 | 1.377 (3) |
| C3—C4 | 1.376 (3) | C10—C11 | 1.368 (3) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.379 (3) | C11—C12 | 1.372 (3) |
| C4—H4 | 0.9300 | C11—H11 | 0.9300 |
| C5—C6 | 1.376 (3) | C12—C13 | 1.383 (3) |
| C5—H5 | 0.9300 | C12—H12 | 0.9300 |
| C7—H7 | 0.9300 | C14—H14 | 0.9300 |
| C7—N1—O1 | 111.93 (15) | C14—N2—O2 | 111.98 (15) |
| N1—O1—H1 | 109.5 | N2—O2—H2 | 109.5 |
| C6—C1—C2 | 115.78 (16) | C13—C8—C9 | 115.73 (16) |
| C6—C1—C7 | 124.33 (15) | C13—C8—C14 | 124.76 (16) |
| C2—C1—C7 | 119.86 (15) | C9—C8—C14 | 119.50 (15) |
| C3—C2—C1 | 123.02 (18) | C10—C9—C8 | 122.98 (18) |
| C3—C2—Cl1 | 118.10 (15) | C10—C9—Cl3 | 118.38 (15) |
| C1—C2—Cl1 | 118.86 (14) | C8—C9—Cl3 | 118.63 (14) |
| C4—C3—C2 | 118.71 (18) | C11—C10—C9 | 119.02 (19) |
| C4—C3—H3 | 120.6 | C11—C10—H10 | 120.5 |
| C2—C3—H3 | 120.6 | C9—C10—H10 | 120.5 |
| C3—C4—C5 | 120.56 (19) | C10—C11—C12 | 120.62 (19) |
| C3—C4—H4 | 119.7 | C10—C11—H11 | 119.7 |
| C5—C4—H4 | 119.7 | C12—C11—H11 | 119.7 |
| C6—C5—C4 | 119.7 (2) | C11—C12—C13 | 119.8 (2) |
| C6—C5—H5 | 120.2 | C11—C12—H12 | 120.1 |
| C4—C5—H5 | 120.2 | C13—C12—H12 | 120.1 |
| C5—C6—C1 | 122.23 (17) | C12—C13—C8 | 121.80 (18) |
| C5—C6—Cl2 | 117.14 (15) | C12—C13—Cl4 | 117.71 (16) |
| C1—C6—Cl2 | 120.61 (13) | C8—C13—Cl4 | 120.46 (14) |
| N1—C7—C1 | 121.30 (16) | N2—C14—C8 | 121.45 (16) |
| N1—C7—H7 | 119.4 | N2—C14—H14 | 119.3 |
| C1—C7—H7 | 119.4 | C8—C14—H14 | 119.3 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1i | 0.82 | 2.14 | 2.854 (2) | 145 |
| O2—H2···N2ii | 0.82 | 2.15 | 2.850 (2) | 144 |
| Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1i | 0.82 | 2.14 | 2.854 (2) | 145 |
| O2—H2···N2ii | 0.82 | 2.15 | 2.850 (2) | 144 |
| Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+2, −z+1. |
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2,6-Dichlorobenzaldehyde oxime, is an important intermediate for organic synthesis(Xu & Jin,1999). As part of our task, we have synthesized the title compound (I) .
In the title compound, C7H6Cl2NO, there are two molecules in the asymmetric unit. Both molecules are roughly identical, the oxime fragment is twisted with respect to the dichlorobenzene ring by 53.83 (11)° and 42.99 (14)° respectively (Fig. 1).
Each molecule is connected to its symmetry related one through inversion center by O-H···N hydrogen bonds building a R22(6) graph-set motif (Etter et al., 1990; Bernstein et al., 1995) (Fig. 2 and Table 1).