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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o25.
Published online 2009 December 4. doi:  10.1107/S1600536809051526
PMCID: PMC2980139

7-Chloro­indoline-2,3-dione

Abstract

There are two mol­ecules in the asymmetric unit of the title compound, C8H4ClNO2. In the crystal, they are linked by N—H(...)O hydrogen bonds, generating centrosymmetric, tetra­meric assemblies. A C—H(...)O inter­action also occurs.

Related literature

For general background to oxyphenastatin derivatives and further synthetic details, see: Uddin et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-66-00o25-scheme1.jpg

Experimental

Crystal data

  • C8H4ClNO2
  • M r = 181.57
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o25-efi1.jpg
  • a = 7.2450 (14) Å
  • b = 8.6080 (17) Å
  • c = 12.470 (3) Å
  • α = 86.95 (3)°
  • β = 78.02 (3)°
  • γ = 84.89 (3)°
  • V = 757.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.45 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.876, T max = 0.956
  • 2988 measured reflections
  • 2749 independent reflections
  • 2051 reflections with I > 2σ(I)
  • R int = 0.047
  • 3 standard reflections every 200 reflections
  • intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.160
  • S = 1.01
  • 2749 reflections
  • 217 parameters
  • 13 restraints
  • H-atom parameters constrained
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051526/hb5233sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051526/hb5233Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis of Nanjing University for support.

supplementary crystallographic information

Experimental

85 g (0.06 mol) Sodium sulfate and 300 ml water was added into a 1000 ml three mouthed flask, mixed till the sodium sulfate dissolved, then a saturated solution of 18 g (0.11 mol) chloral hydrate was added. While stirring, the mixture of 12.7 g (0.1 mol) p-chloroaniline, 12 ml hydrochloric acid and 100 ml water was dropped to the reaction mixture causing white precipitation. Then 22 g (0.32 mol) hydroxylamine hydrochloride was added and the mixture was heated to 348 K. After 5 h, light yellow precipitation appeared, filtered and washed with water, dried and then added the yellow precipitation into concentrated sulfuric acid (50 ml) in batches at 353 K. Heated to 363 K and stirred for 30 minutes and dumped the mixture into ice water (1000 ml), stirred for 40 minutes, filtered and washed with water to neutral, dried and Yellow blocks of (I) were obtained by slow evaporation of an acetone solution (yield; 90%, m.p. 463 K).

Refinement

H atoms were positioned geometrically, with N—H = 0.86Å and C—H = 0.93Å and refined as riding with Uiso(H) = xUeq(C,O,N), where x = 1.5 for NH H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C8H4ClNO2Z = 4
Mr = 181.57F(000) = 368
Triclinic, P1Dx = 1.593 Mg m3
Hall symbol: -P 1Melting point: 463K K
a = 7.2450 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.6080 (17) ÅCell parameters from 25 reflections
c = 12.470 (3) Åθ = 9–13°
α = 86.95 (3)°µ = 0.45 mm1
β = 78.02 (3)°T = 293 K
γ = 84.89 (3)°Block, yellow
V = 757.2 (3) Å30.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer2051 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
graphiteθmax = 25.3°, θmin = 1.7°
ω/2θ scansh = 0→8
Absorption correction: ψ scan (North et al., 1968)k = −10→10
Tmin = 0.876, Tmax = 0.956l = −14→14
2988 measured reflections3 standard reflections every 200 reflections
2749 independent reflections intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.1P)2 + 0.250P] where P = (Fo2 + 2Fc2)/3
2749 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.63 e Å3
13 restraintsΔρmin = −0.29 e Å3

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
Cl10.28644 (18)0.90528 (12)0.43418 (10)0.0839 (4)
N10.4403 (4)0.6203 (3)0.28727 (19)0.0415 (6)
H1A0.45990.70990.25500.050*
O10.4519 (4)0.2163 (3)0.3096 (2)0.0731 (8)
O20.5909 (4)0.4581 (3)0.1488 (2)0.0662 (7)
C10.1629 (6)0.4991 (7)0.6003 (3)0.0780 (13)
H1B0.10190.46740.67020.094*
C20.1735 (5)0.6597 (6)0.5739 (3)0.0701 (11)
H2A0.12010.73280.62610.084*
C30.2638 (5)0.7090 (4)0.4697 (3)0.0541 (9)
C40.3423 (4)0.5985 (4)0.3954 (2)0.0393 (7)
C50.3300 (4)0.4400 (4)0.4231 (3)0.0462 (8)
C60.2399 (5)0.3892 (5)0.5258 (3)0.0636 (11)
H6A0.23210.28340.54350.076*
C70.4285 (5)0.3544 (4)0.3265 (3)0.0472 (8)
C80.5004 (4)0.4814 (4)0.2399 (3)0.0441 (7)
Cl20.12910 (13)0.66786 (10)0.12400 (7)0.0589 (3)
N20.3136 (3)0.9103 (3)−0.04844 (19)0.0353 (5)
H2B0.37370.88320.00310.042*
O30.2217 (4)1.0991 (3)−0.2813 (2)0.0618 (7)
O40.4995 (3)1.1009 (3)−0.13853 (18)0.0533 (6)
C9−0.1833 (5)0.7602 (4)−0.1086 (3)0.0486 (8)
H9A−0.29480.7290−0.12350.058*
C10−0.0841 (4)0.8681 (4)−0.1775 (3)0.0472 (8)
H10A−0.12820.9111−0.23840.057*
C110.0833 (4)0.9115 (3)−0.1544 (2)0.0403 (7)
C120.1483 (4)0.8492 (3)−0.0617 (2)0.0352 (6)
C130.0469 (4)0.7416 (3)0.0075 (2)0.0414 (7)
C14−0.1181 (4)0.6972 (4)−0.0167 (3)0.0446 (7)
H14A−0.18660.62430.02900.053*
C150.3646 (4)1.0178 (4)−0.1286 (2)0.0438 (7)
C160.2210 (4)1.0242 (4)−0.2053 (3)0.0473 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1048 (9)0.0609 (6)0.0837 (8)0.0087 (6)−0.0158 (6)−0.0213 (5)
N10.0483 (14)0.0400 (13)0.0346 (13)−0.0113 (11)−0.0040 (11)0.0076 (10)
O10.102 (2)0.0405 (14)0.083 (2)−0.0138 (13)−0.0326 (17)0.0086 (13)
O20.0718 (17)0.0661 (16)0.0523 (15)−0.0055 (13)0.0086 (13)−0.0098 (12)
C10.049 (2)0.144 (4)0.040 (2)−0.025 (2)−0.0059 (17)0.025 (2)
C20.050 (2)0.116 (3)0.0408 (19)0.003 (2)−0.0039 (16)−0.010 (2)
C30.0449 (18)0.073 (2)0.0444 (18)−0.0010 (16)−0.0110 (15)−0.0040 (16)
C40.0342 (15)0.0512 (17)0.0333 (15)−0.0076 (12)−0.0091 (12)0.0059 (13)
C50.0420 (16)0.0554 (19)0.0443 (17)−0.0175 (14)−0.0149 (14)0.0180 (14)
C60.054 (2)0.092 (3)0.049 (2)−0.029 (2)−0.0186 (18)0.033 (2)
C70.0547 (19)0.0435 (18)0.0501 (19)−0.0152 (14)−0.0237 (16)0.0084 (14)
C80.0424 (17)0.0451 (17)0.0440 (18)−0.0062 (13)−0.0062 (14)0.0011 (13)
Cl20.0661 (6)0.0547 (5)0.0548 (5)−0.0123 (4)−0.0093 (4)0.0095 (4)
N20.0392 (13)0.0354 (12)0.0323 (12)−0.0086 (10)−0.0088 (10)0.0054 (10)
O30.0607 (15)0.0807 (18)0.0447 (14)0.0069 (13)−0.0190 (12)0.0044 (13)
O40.0564 (14)0.0499 (13)0.0496 (13)−0.0119 (11)−0.0020 (11)0.0135 (10)
C90.0388 (16)0.0509 (18)0.057 (2)−0.0076 (14)−0.0067 (15)−0.0162 (16)
C100.0406 (17)0.0563 (19)0.0460 (18)0.0031 (15)−0.0118 (14)−0.0118 (15)
C110.0371 (15)0.0433 (16)0.0394 (16)−0.0018 (12)−0.0046 (13)−0.0074 (13)
C120.0326 (14)0.0329 (14)0.0371 (15)−0.0030 (11)0.0010 (12)−0.0052 (11)
C130.0405 (16)0.0378 (15)0.0429 (17)−0.0050 (12)0.0005 (13)−0.0080 (13)
C140.0376 (16)0.0398 (16)0.0521 (18)−0.0101 (12)0.0046 (14)−0.0058 (13)
C150.0442 (17)0.0437 (16)0.0406 (16)−0.0105 (14)−0.0012 (14)0.0070 (13)
C160.0441 (18)0.0392 (16)0.055 (2)−0.0014 (13)−0.0017 (15)−0.0040 (15)

Geometric parameters (Å, °)

Cl1—C31.737 (4)Cl2—C131.749 (3)
N1—C81.358 (4)N2—C151.342 (4)
N1—C41.399 (4)N2—C121.393 (4)
N1—H1A0.8600N2—H2B0.8600
O1—C71.210 (4)O3—C161.116 (4)
O2—C81.205 (4)O4—C151.244 (4)
C1—C61.362 (6)C9—C101.377 (5)
C1—C21.410 (7)C9—C141.394 (5)
C1—H1B0.9300C9—H9A0.9300
C2—C31.391 (5)C10—C111.389 (4)
C2—H2A0.9300C10—H10A0.9300
C3—C41.366 (5)C11—C121.401 (4)
C4—C51.396 (4)C11—C161.478 (4)
C5—C61.379 (5)C12—C131.384 (4)
C5—C71.465 (5)C13—C141.382 (4)
C6—H6A0.9300C14—H14A0.9300
C7—C81.541 (4)C15—C161.548 (5)
C8—N1—C4111.1 (2)C15—N2—C12109.5 (2)
C8—N1—H1A124.5C15—N2—H2B125.2
C4—N1—H1A124.5C12—N2—H2B125.2
C6—C1—C2121.4 (3)C10—C9—C14120.5 (3)
C6—C1—H1B119.3C10—C9—H9A119.7
C2—C1—H1B119.3C14—C9—H9A119.7
C3—C2—C1120.0 (4)C9—C10—C11118.7 (3)
C3—C2—H2A120.0C9—C10—H10A120.6
C1—C2—H2A120.0C11—C10—H10A120.6
C4—C3—C2118.4 (4)C10—C11—C12120.8 (3)
C4—C3—Cl1119.7 (3)C10—C11—C16134.1 (3)
C2—C3—Cl1121.8 (3)C12—C11—C16105.0 (3)
C3—C4—C5120.7 (3)C13—C12—N2126.7 (3)
C3—C4—N1128.4 (3)C13—C12—C11120.1 (3)
C5—C4—N1110.9 (3)N2—C12—C11113.2 (2)
C6—C5—C4121.6 (4)C14—C13—C12118.9 (3)
C6—C5—C7131.6 (3)C14—C13—Cl2121.9 (2)
C4—C5—C7106.8 (3)C12—C13—Cl2119.2 (2)
C1—C6—C5117.9 (4)C13—C14—C9121.0 (3)
C1—C6—H6A121.1C13—C14—H14A119.5
C5—C6—H6A121.1C9—C14—H14A119.5
O1—C7—C5131.5 (3)O4—C15—N2126.6 (3)
O1—C7—C8123.4 (3)O4—C15—C16125.7 (3)
C5—C7—C8105.0 (3)N2—C15—C16107.7 (3)
O2—C8—N1128.3 (3)O3—C16—C11128.3 (3)
O2—C8—C7125.5 (3)O3—C16—C15127.2 (3)
N1—C8—C7106.2 (3)C11—C16—C15104.5 (3)
C6—C1—C2—C30.1 (6)C14—C9—C10—C110.8 (5)
C1—C2—C3—C4−0.7 (5)C9—C10—C11—C12−1.3 (4)
C1—C2—C3—Cl1−178.2 (3)C9—C10—C11—C16−177.5 (3)
C2—C3—C4—C50.8 (5)C15—N2—C12—C13−176.5 (3)
Cl1—C3—C4—C5178.4 (2)C15—N2—C12—C111.6 (3)
C2—C3—C4—N1−179.5 (3)C10—C11—C12—C130.8 (4)
Cl1—C3—C4—N1−1.9 (5)C16—C11—C12—C13178.0 (2)
C8—N1—C4—C3178.8 (3)C10—C11—C12—N2−177.4 (2)
C8—N1—C4—C5−1.5 (4)C16—C11—C12—N2−0.2 (3)
C3—C4—C5—C6−0.4 (5)N2—C12—C13—C14178.0 (3)
N1—C4—C5—C6179.8 (3)C11—C12—C13—C140.1 (4)
C3—C4—C5—C7−179.6 (3)N2—C12—C13—Cl2−1.0 (4)
N1—C4—C5—C70.6 (3)C11—C12—C13—Cl2−179.0 (2)
C2—C1—C6—C50.3 (6)C12—C13—C14—C9−0.6 (4)
C4—C5—C6—C1−0.1 (5)Cl2—C13—C14—C9178.5 (2)
C7—C5—C6—C1178.8 (3)C10—C9—C14—C130.1 (5)
C6—C5—C7—O12.9 (6)C12—N2—C15—O4176.1 (3)
C4—C5—C7—O1−178.1 (4)C12—N2—C15—C16−2.2 (3)
C6—C5—C7—C8−178.7 (3)C10—C11—C16—O3−3.6 (6)
C4—C5—C7—C80.3 (3)C12—C11—C16—O3179.8 (3)
C4—N1—C8—O2−178.7 (3)C10—C11—C16—C15175.6 (3)
C4—N1—C8—C71.6 (3)C12—C11—C16—C15−1.0 (3)
O1—C7—C8—O2−2.3 (5)O4—C15—C16—O32.9 (6)
C5—C7—C8—O2179.1 (3)N2—C15—C16—O3−178.8 (3)
O1—C7—C8—N1177.4 (3)O4—C15—C16—C11−176.3 (3)
C5—C7—C8—N1−1.2 (3)N2—C15—C16—C112.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.862.122.961 (4)165
N2—H2B···O4i0.862.102.923 (3)160
C14—H14A···O2ii0.932.463.385 (4)172

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5233).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft. The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Uddin, M. K., Reignier, S. G., Coulter, T., Montalbetti, C., Granas, C., Butcher, S., Krog-Jensen, C. & Felding, J. (2007). Bioorg Med. Chem. Lett.17, 2854–2857. [PubMed]

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