PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1762.
Published online 2009 July 4. doi:  10.1107/S1600536809024970
PMCID: PMC2977334

2-(2,6-Dichloro­benz­yl)pyrrolidine-1,3-dione

Abstract

In the title compound, C11H9Cl2NO2, the dihedral anngle between the mean planes of the aromatic ring and the twisted pyrrolidinedione ring is 79.98 (9)°.

Related literature

For the synthesis, see: Duan et al. (2005 [triangle]). For the pharmaceutical properties of pyrrolidine-2,5-dione derivatives, see: Obniska et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1762-scheme1.jpg

Experimental

Crystal data

  • C11H9Cl2NO2
  • M r = 258.09
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1762-efi1.jpg
  • a = 4.8057 (5) Å
  • b = 9.4388 (8) Å
  • c = 23.936 (2) Å
  • V = 1085.74 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.58 mm−1
  • T = 113 K
  • 0.14 × 0.12 × 0.10 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.923, T max = 0.944
  • 7528 measured reflections
  • 2562 independent reflections
  • 2400 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.073
  • S = 1.09
  • 2562 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.27 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1017 Friedel pairs
  • Flack parameter: 0.01 (6)

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024970/hb5015sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024970/hb5015Isup2.hkl

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

Acknowledgments

This work was supported by the Changsha Science and Technology Bureau (k0803061-11) and the Scientific Research Foundation of Hunan Provience (S2007F123).

supplementary crystallographic information

Comment

The derivatives of pyrrolidine-2,5-dione possess valuable pharmaceutical properties (Obniska et al., 2009). In this paper, synthesis and the crystal structure of the title compound, (I), Fig 1, is reported.

Experimental

The title compound was prepared according to the procedure of Duan et al. (2005). The title compound (40 mg) was dissolved in a mixture of chloroform (5 ml) and ethanol (3 ml) and the solution was kept at room temperature for 15 days. Evaporation of the solution gave colourless blocks of (I).

Refinement

All H atoms were included in the idealized positions (C—H = 0.93–0.99Å) and refined as riding with and refined in a riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as spheres of arbitrary radius.

Crystal data

C11H9Cl2NO2Dx = 1.579 Mg m3
Mr = 258.09Melting point = 409–411 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2abCell parameters from 2881 reflections
a = 4.8057 (5) Åθ = 1.7–27.9°
b = 9.4388 (8) ŵ = 0.58 mm1
c = 23.936 (2) ÅT = 113 K
V = 1085.74 (18) Å3Block, colorless
Z = 40.14 × 0.12 × 0.10 mm
F(000) = 528

Data collection

Rigaku Saturn CCD area-detector diffractometer2562 independent reflections
Radiation source: rotating anode2400 reflections with I > 2σ(I)
confocalRint = 0.029
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.7°
ω and [var phi] scansh = −4→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −12→12
Tmin = 0.923, Tmax = 0.944l = −30→31
7528 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031w = 1/[σ2(Fo2) + (0.0337P)2 + 0.1572P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.073(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.28 e Å3
2562 reflectionsΔρmin = −0.27 e Å3
146 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.027 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1017 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.01 (6)

Special details

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 > 2sigma(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
Cl10.00935 (11)−0.15827 (4)0.039298 (15)0.02779 (12)
Cl2−0.01306 (10)0.14810 (5)0.231345 (15)0.02661 (12)
O1−0.4371 (3)0.35252 (13)0.15425 (5)0.0256 (3)
O20.2345 (3)0.17916 (13)0.03882 (5)0.0258 (3)
N1−0.1077 (3)0.23490 (14)0.10180 (5)0.0172 (3)
C1−0.2311 (4)0.35434 (18)0.12493 (6)0.0201 (3)
C2−0.0631 (4)0.48127 (18)0.10689 (8)0.0276 (4)
H2A0.05140.51740.13820.033*
H2B−0.18630.55820.09360.033*
C30.1211 (4)0.42692 (18)0.05958 (7)0.0222 (4)
H3A0.05200.46040.02290.027*
H3B0.31560.45910.06450.027*
C40.1017 (4)0.26745 (17)0.06376 (6)0.0186 (3)
C5−0.2043 (4)0.09082 (17)0.11224 (6)0.0177 (3)
H5A−0.27350.04960.07680.021*
H5B−0.36190.09390.13890.021*
C60.0205 (4)−0.00365 (15)0.13563 (6)0.0160 (3)
C70.1336 (4)−0.11631 (17)0.10562 (7)0.0193 (3)
C80.3417 (4)−0.20312 (18)0.12690 (8)0.0255 (4)
H80.4149−0.27830.10500.031*
C90.4416 (4)−0.17880 (19)0.18054 (8)0.0283 (4)
H90.5851−0.23700.19530.034*
C100.3327 (4)−0.0703 (2)0.21228 (7)0.0253 (4)
H100.3987−0.05380.24910.030*
C110.1251 (4)0.01445 (17)0.18967 (7)0.0195 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0382 (3)0.0230 (2)0.02216 (19)0.0038 (2)−0.0022 (2)−0.00636 (14)
Cl20.0287 (2)0.0340 (2)0.01716 (18)0.0004 (2)−0.00099 (17)−0.00597 (15)
O10.0261 (7)0.0286 (6)0.0223 (5)0.0089 (6)0.0024 (5)−0.0028 (5)
O20.0255 (7)0.0264 (7)0.0254 (6)0.0043 (5)0.0073 (5)0.0028 (5)
N10.0175 (7)0.0171 (6)0.0171 (6)0.0008 (6)0.0003 (6)−0.0001 (5)
C10.0224 (9)0.0194 (8)0.0186 (7)0.0029 (7)−0.0033 (6)−0.0012 (6)
C20.0315 (11)0.0185 (7)0.0329 (9)−0.0017 (8)−0.0009 (8)−0.0001 (7)
C30.0218 (9)0.0207 (8)0.0242 (8)−0.0039 (7)−0.0037 (7)0.0034 (7)
C40.0177 (8)0.0227 (8)0.0155 (7)0.0009 (7)−0.0020 (6)0.0018 (6)
C50.0188 (8)0.0153 (7)0.0189 (7)−0.0005 (6)−0.0016 (7)−0.0002 (6)
C60.0141 (8)0.0167 (7)0.0174 (6)−0.0022 (7)−0.0003 (6)0.0030 (5)
C70.0185 (8)0.0183 (7)0.0210 (7)−0.0012 (7)−0.0001 (7)0.0023 (6)
C80.0231 (10)0.0179 (8)0.0354 (9)0.0017 (7)0.0043 (8)0.0042 (7)
C90.0215 (10)0.0245 (9)0.0388 (10)0.0014 (8)−0.0007 (8)0.0156 (7)
C100.0221 (10)0.0303 (9)0.0235 (8)−0.0061 (8)−0.0035 (7)0.0109 (7)
C110.0172 (8)0.0223 (8)0.0190 (7)−0.0021 (7)0.0014 (7)0.0031 (6)

Geometric parameters (Å, °)

Cl1—C71.7417 (17)C3—H3B0.9900
Cl2—C111.7400 (17)C5—C61.509 (2)
O1—C11.213 (2)C5—H5A0.9900
O2—C41.208 (2)C5—H5B0.9900
N1—C11.389 (2)C6—C71.394 (2)
N1—C41.391 (2)C6—C111.398 (2)
N1—C51.459 (2)C7—C81.390 (2)
C1—C21.508 (2)C8—C91.390 (3)
C2—C31.526 (3)C8—H80.9500
C2—H2A0.9900C9—C101.378 (3)
C2—H2B0.9900C9—H90.9500
C3—C41.511 (2)C10—C111.389 (2)
C3—H3A0.9900C10—H100.9500
C1—N1—C4112.99 (14)C6—C5—H5A109.0
C1—N1—C5123.52 (14)N1—C5—H5B109.0
C4—N1—C5123.25 (13)C6—C5—H5B109.0
O1—C1—N1124.58 (16)H5A—C5—H5B107.8
O1—C1—C2127.86 (16)C7—C6—C11115.46 (15)
N1—C1—C2107.56 (14)C7—C6—C5122.61 (14)
C1—C2—C3104.84 (14)C11—C6—C5121.91 (14)
C1—C2—H2A110.8C8—C7—C6122.79 (16)
C3—C2—H2A110.8C8—C7—Cl1116.53 (14)
C1—C2—H2B110.8C6—C7—Cl1120.64 (13)
C3—C2—H2B110.8C7—C8—C9119.33 (17)
H2A—C2—H2B108.9C7—C8—H8120.3
C4—C3—C2104.48 (14)C9—C8—H8120.3
C4—C3—H3A110.9C10—C9—C8120.04 (16)
C2—C3—H3A110.9C10—C9—H9120.0
C4—C3—H3B110.9C8—C9—H9120.0
C2—C3—H3B110.9C9—C10—C11119.09 (16)
H3A—C3—H3B108.9C9—C10—H10120.5
O2—C4—N1123.60 (15)C11—C10—H10120.5
O2—C4—C3128.46 (16)C10—C11—C6123.25 (16)
N1—C4—C3107.93 (14)C10—C11—Cl2117.94 (13)
N1—C5—C6112.74 (14)C6—C11—Cl2118.80 (13)
N1—C5—H5A109.0
C4—N1—C1—O1171.59 (15)N1—C5—C6—C1169.50 (19)
C5—N1—C1—O1−3.0 (2)C11—C6—C7—C8−1.7 (2)
C4—N1—C1—C2−8.48 (18)C5—C6—C7—C8179.66 (15)
C5—N1—C1—C2176.92 (14)C11—C6—C7—Cl1176.23 (12)
O1—C1—C2—C3−165.92 (16)C5—C6—C7—Cl1−2.4 (2)
N1—C1—C2—C314.14 (18)C6—C7—C8—C90.7 (3)
C1—C2—C3—C4−14.26 (18)Cl1—C7—C8—C9−177.37 (14)
C1—N1—C4—O2−179.73 (16)C7—C8—C9—C100.6 (3)
C5—N1—C4—O2−5.1 (3)C8—C9—C10—C11−0.7 (3)
C1—N1—C4—C3−1.03 (18)C9—C10—C11—C6−0.5 (3)
C5—N1—C4—C3173.59 (14)C9—C10—C11—Cl2178.68 (13)
C2—C3—C4—O2−171.54 (18)C7—C6—C11—C101.7 (2)
C2—C3—C4—N19.84 (18)C5—C6—C11—C10−179.73 (16)
C1—N1—C5—C6−123.48 (16)C7—C6—C11—Cl2−177.52 (13)
C4—N1—C5—C662.46 (19)C5—C6—C11—Cl21.1 (2)
N1—C5—C6—C7−111.97 (17)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5015).

References

  • Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005). Fine Chem.22, 39–40, 52.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Obniska, J., Kaminski, K., Skrzynska, D. & Pichor, J. (2009). Eur. J. Med. Chem.44, 2224–2233. [PubMed]
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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