PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o2024.
Published online 2008 September 27. doi:  10.1107/S1600536808030559
PMCID: PMC2959404

1-(4-Chloro­phen­yl)-3-(2-nitro­phenyl)propane-1,2-dione

Abstract

The title compound, C15H10ClNO4, belongs to the class of 1,2-diketones, which have important applications in both synthetic organic chemistry and supra­molecular chemistry. A dihedral angle of 9.03 (1)° is found between the mean planes of the two benzene rings. C—H(...)O inter­actions help to stabilize the crystal structure.

Related literature

For the synthesis of the title compound, see: Barnes & Gist (1950 [triangle]). For applications of the title compound, see: Saalfrank et al. (1988 [triangle]); Schobert (1988 [triangle]); van Leusen & van Leusen (1977 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2024-scheme1.jpg

Experimental

Crystal data

  • C15H10ClNO4
  • M r = 303.69
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2024-efi1.jpg
  • a = 7.9995 (3) Å
  • b = 6.3730 (2) Å
  • c = 26.7750 (5) Å
  • β = 91.340 (2)°
  • V = 1364.64 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 298 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.943, T max = 0.971
  • 8762 measured reflections
  • 2408 independent reflections
  • 1872 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.133
  • S = 1.07
  • 2408 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 1999 [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 I, global. DOI: 10.1107/S1600536808030559/cs2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030559/cs2095Isup2.hkl

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

Acknowledgments

The authors are grateful to Xiangfan University for financial support.

supplementary crystallographic information

Comment

1,2-Diketones are important intermediates in the preparation of heterocyclic compounds in synthetic chemistry (van Leusen & van Leusen, 1977; Saalfrank et al., 1988). In addition, they can also be used as ligands in supramolecular chemistry (Schobert, 1988). The molecular structure of the title compound is shown in Fig. 1. The dihedral angle of the two benzene rings is 9.03 (1)°. Molecules are mainly connected by an intermolecular C—H···O interaction.

Experimental

The title compound was synthesized as previously described by Barnes & Gist (1950). Colorless crystals suitable for X-ray data collection were obtained by slow evaporation of a 5:2 ratio CH2Cl2:MeOH solution at 293 K.

Refinement

All H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2 Ueq(C) (1.5Ueq(C) for methyl) of the parent atoms.

Figures

Fig. 1.
View of the title molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius.

Crystal data

C15H10ClNO4F(000) = 624
Mr = 303.69Dx = 1.478 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2433 reflections
a = 7.9995 (3) Åθ = 2.6–23.4°
b = 6.3730 (2) ŵ = 0.30 mm1
c = 26.7750 (5) ÅT = 298 K
β = 91.340 (2)°Block, colourless
V = 1364.64 (7) Å30.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer2408 independent reflections
Radiation source: fine-focus sealed tube1872 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −9→9
Tmin = 0.943, Tmax = 0.971k = −7→7
8762 measured reflectionsl = −31→31

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0688P)2 + 0.2924P] where P = (Fo2 + 2Fc2)/3
2408 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = −0.28 e Å3

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

xyzUiso*/Ueq
C10.4590 (2)0.5187 (3)0.67527 (7)0.0496 (5)
C20.4028 (3)0.7133 (3)0.65828 (7)0.0498 (5)
C30.2727 (3)0.8197 (4)0.68005 (9)0.0606 (6)
H30.23820.94920.66760.073*
C40.1952 (3)0.7326 (5)0.72019 (9)0.0675 (7)
H40.10750.80280.73510.081*
C50.2471 (3)0.5421 (4)0.73831 (9)0.0669 (7)
H50.19470.48290.76560.080*
C60.3771 (3)0.4379 (4)0.71616 (8)0.0588 (6)
H60.41110.30890.72910.071*
C70.6000 (3)0.3935 (4)0.65391 (9)0.0602 (6)
H7A0.60180.25610.66950.072*
H7B0.57770.37350.61850.072*
C80.7691 (3)0.4913 (3)0.66072 (7)0.0504 (5)
C90.9136 (3)0.3769 (4)0.63586 (8)0.0539 (5)
C101.0144 (2)0.4879 (3)0.59876 (7)0.0471 (5)
C111.1423 (3)0.3809 (4)0.57538 (8)0.0568 (6)
H111.16650.24330.58460.068*
C121.2338 (3)0.4757 (4)0.53865 (8)0.0631 (6)
H121.31830.40290.52280.076*
C131.1976 (3)0.6808 (4)0.52582 (8)0.0571 (6)
C141.0729 (3)0.7893 (4)0.54892 (8)0.0572 (6)
H141.05050.92780.54010.069*
C150.9814 (3)0.6933 (3)0.58507 (8)0.0536 (5)
H150.89650.76690.60050.064*
Cl11.31213 (9)0.80635 (13)0.48046 (2)0.0813 (3)
N10.4783 (3)0.8163 (4)0.61492 (7)0.0653 (6)
O10.5769 (2)0.7162 (4)0.58971 (7)0.0969 (7)
O20.4318 (3)0.9934 (3)0.60410 (8)0.0994 (7)
O30.79710 (19)0.6406 (3)0.68656 (6)0.0693 (5)
O40.9394 (2)0.1971 (3)0.64872 (8)0.0855 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0428 (11)0.0539 (13)0.0520 (11)−0.0072 (9)−0.0024 (9)−0.0057 (10)
C20.0441 (11)0.0588 (14)0.0463 (11)−0.0084 (10)−0.0063 (9)−0.0001 (10)
C30.0509 (13)0.0614 (15)0.0687 (15)0.0020 (11)−0.0109 (11)−0.0052 (11)
C40.0447 (13)0.0881 (19)0.0697 (15)0.0040 (12)0.0022 (11)−0.0143 (14)
C50.0516 (14)0.0881 (19)0.0614 (14)−0.0112 (13)0.0082 (11)0.0013 (13)
C60.0538 (13)0.0602 (14)0.0623 (13)−0.0091 (11)−0.0032 (10)0.0065 (11)
C70.0574 (14)0.0606 (14)0.0627 (13)−0.0031 (11)0.0040 (10)−0.0117 (11)
C80.0533 (13)0.0521 (13)0.0461 (11)0.0014 (10)0.0050 (9)0.0032 (10)
C90.0544 (13)0.0497 (13)0.0579 (12)0.0040 (10)0.0038 (10)0.0016 (10)
C100.0448 (11)0.0478 (12)0.0485 (11)0.0002 (9)−0.0008 (9)−0.0050 (9)
C110.0542 (13)0.0491 (13)0.0676 (14)0.0044 (10)0.0066 (10)−0.0056 (10)
C120.0537 (14)0.0705 (17)0.0655 (14)0.0015 (12)0.0141 (11)−0.0154 (12)
C130.0509 (13)0.0724 (17)0.0479 (12)−0.0099 (11)0.0004 (10)−0.0030 (10)
C140.0580 (13)0.0548 (13)0.0589 (13)−0.0014 (11)0.0016 (10)0.0049 (10)
C150.0492 (12)0.0549 (14)0.0568 (12)0.0055 (10)0.0047 (9)0.0001 (10)
Cl10.0776 (5)0.1050 (6)0.0619 (4)−0.0200 (4)0.0179 (3)0.0070 (3)
N10.0593 (12)0.0772 (16)0.0588 (12)−0.0135 (11)−0.0082 (10)0.0125 (11)
O10.0753 (13)0.143 (2)0.0732 (13)0.0231 (13)0.0198 (10)0.0355 (12)
O20.140 (2)0.0620 (13)0.0966 (14)−0.0183 (13)0.0092 (13)0.0166 (11)
O30.0546 (9)0.0763 (11)0.0774 (11)−0.0077 (8)0.0083 (8)−0.0257 (9)
O40.0905 (14)0.0608 (12)0.1068 (14)0.0187 (10)0.0394 (11)0.0232 (10)

Geometric parameters (Å, °)

C1—C61.388 (3)C8—C91.532 (3)
C1—C21.392 (3)C9—O41.213 (3)
C1—C71.505 (3)C9—C101.475 (3)
C2—C31.382 (3)C10—C151.383 (3)
C2—N11.475 (3)C10—C111.390 (3)
C3—C41.371 (3)C11—C121.379 (3)
C3—H30.9300C11—H110.9300
C4—C51.368 (4)C12—C131.380 (3)
C4—H40.9300C12—H120.9300
C5—C61.380 (3)C13—C141.373 (3)
C5—H50.9300C13—Cl11.734 (2)
C6—H60.9300C14—C151.371 (3)
C7—C81.497 (3)C14—H140.9300
C7—H7A0.9700C15—H150.9300
C7—H7B0.9700N1—O21.221 (3)
C8—O31.195 (3)N1—O11.229 (3)
C6—C1—C2115.7 (2)C7—C8—C9115.99 (19)
C6—C1—C7118.3 (2)O4—C9—C10123.5 (2)
C2—C1—C7126.0 (2)O4—C9—C8116.8 (2)
C3—C2—C1122.7 (2)C10—C9—C8119.63 (19)
C3—C2—N1116.1 (2)C15—C10—C11118.9 (2)
C1—C2—N1121.2 (2)C15—C10—C9121.91 (19)
C4—C3—C2119.4 (2)C11—C10—C9119.2 (2)
C4—C3—H3120.3C12—C11—C10120.9 (2)
C2—C3—H3120.3C12—C11—H11119.5
C5—C4—C3119.9 (2)C10—C11—H11119.5
C5—C4—H4120.1C11—C12—C13118.7 (2)
C3—C4—H4120.1C11—C12—H12120.6
C4—C5—C6120.0 (2)C13—C12—H12120.6
C4—C5—H5120.0C14—C13—C12121.0 (2)
C6—C5—H5120.0C14—C13—Cl1119.0 (2)
C5—C6—C1122.3 (2)C12—C13—Cl1119.99 (18)
C5—C6—H6118.8C15—C14—C13119.9 (2)
C1—C6—H6118.8C15—C14—H14120.0
C8—C7—C1114.60 (19)C13—C14—H14120.0
C8—C7—H7A108.6C14—C15—C10120.5 (2)
C1—C7—H7A108.6C14—C15—H15119.7
C8—C7—H7B108.6C10—C15—H15119.7
C1—C7—H7B108.6O2—N1—O1123.0 (2)
H7A—C7—H7B107.6O2—N1—C2118.0 (2)
O3—C8—C7123.96 (19)O1—N1—C2118.8 (2)
O3—C8—C9119.84 (19)
C6—C1—C2—C3−0.7 (3)O4—C9—C10—C15−179.9 (2)
C7—C1—C2—C3−179.6 (2)C8—C9—C10—C15−0.7 (3)
C6—C1—C2—N1−179.61 (18)O4—C9—C10—C112.6 (3)
C7—C1—C2—N11.4 (3)C8—C9—C10—C11−178.20 (19)
C1—C2—C3—C40.3 (3)C15—C10—C11—C12−0.9 (3)
N1—C2—C3—C4179.30 (19)C9—C10—C11—C12176.7 (2)
C2—C3—C4—C50.1 (3)C10—C11—C12—C130.8 (3)
C3—C4—C5—C6−0.1 (4)C11—C12—C13—C14−0.1 (3)
C4—C5—C6—C1−0.3 (4)C11—C12—C13—Cl1179.04 (17)
C2—C1—C6—C50.7 (3)C12—C13—C14—C15−0.5 (3)
C7—C1—C6—C5179.7 (2)Cl1—C13—C14—C15−179.67 (17)
C6—C1—C7—C8−112.2 (2)C13—C14—C15—C100.4 (3)
C2—C1—C7—C866.7 (3)C11—C10—C15—C140.2 (3)
C1—C7—C8—O39.9 (3)C9—C10—C15—C14−177.2 (2)
C1—C7—C8—C9−175.36 (19)C3—C2—N1—O26.2 (3)
O3—C8—C9—O4115.7 (3)C1—C2—N1—O2−174.8 (2)
C7—C8—C9—O4−59.3 (3)C3—C2—N1—O1−169.5 (2)
O3—C8—C9—C10−63.5 (3)C1—C2—N1—O19.5 (3)
C7—C8—C9—C10121.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.932.533.279 (3)138
C15—H15···O10.932.593.244 (3)128

Symmetry codes: (i) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CS2095).

References

  • Barnes, P. R. & Gist, L. A. (1950). J. Am. Chem. Soc.72, 2509–2510.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Leusen, D. van & van Leusen, A. M. (1977). Tetrahedron Lett.18, 4233–4236.
  • Saalfrank, R. W., Hafner, W., Markmann, J. & Bestmann, H. J. (1988). Tetrahedron, 44, 5095–5100.
  • Schobert, R. (1988). Angew. Chem. Int. Ed.27, 855–856.
  • Sheldrick, G. M. (1997). SADABS University of Göttingen, Germany.
  • 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