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ISSN: 2056-9890

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

aDepartment of Chemistry and Biology, Xiangfan University, Xiangfan 441053, People's Republic of China
*Correspondence e-mail: xfhuanglin@163.com

(Received 10 September 2008; accepted 22 September 2008; online 27 September 2008)

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[Barnes, P. R. & Gist, L. A. (1950). J. Am. Chem. Soc. 72, 2509-2510.]). For applications of the title compound, see: Saalfrank et al. (1988[Saalfrank, R. W., Hafner, W., Markmann, J. & Bestmann, H. J. (1988). Tetrahedron, 44, 5095-5100.]); Schobert (1988[Schobert, R. (1988). Angew. Chem. Int. Ed. 27, 855-856.]); van Leusen & van Leusen (1977[Leusen, D. van & van Leusen, A. M. (1977). Tetrahedron Lett. 18, 4233-4236.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10ClNO4

  • Mr = 303.69

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.943, Tmax = 0.971

  • 8762 measured reflections

  • 2408 independent reflections

  • 1872 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5⋯O3i 0.93 2.53 3.279 (3) 138
C15—H15⋯O1 0.93 2.59 3.244 (3) 128
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 1999); 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).

Figures top
[Figure 1] 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.
1-(4-Chlorophenyl)-3-(2-nitrophenyl)propane-1,2-dione top
Crystal data top
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 top
Bruker SMART 4K CCD area-detector
diffractometer
2408 independent reflections
Radiation source: fine-focus sealed tube1872 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 99
Tmin = 0.943, Tmax = 0.971k = 77
8762 measured reflectionsl = 3131
Refinement top
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 = 1.07 w = 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
Crystal data top
C15H10ClNO4V = 1364.64 (7) Å3
Mr = 303.69Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9995 (3) ŵ = 0.30 mm1
b = 6.3730 (2) ÅT = 298 K
c = 26.7750 (5) Å0.20 × 0.10 × 0.10 mm
β = 91.340 (2)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2408 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
1872 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.971Rint = 0.027
8762 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.07Δρmax = 0.38 e Å3
2408 reflectionsΔρmin = 0.28 e Å3
190 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C30.7 (3)O4—C9—C10—C15179.9 (2)
C7—C1—C2—C3179.6 (2)C8—C9—C10—C150.7 (3)
C6—C1—C2—N1179.61 (18)O4—C9—C10—C112.6 (3)
C7—C1—C2—N11.4 (3)C8—C9—C10—C11178.20 (19)
C1—C2—C3—C40.3 (3)C15—C10—C11—C120.9 (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—C60.1 (4)C11—C12—C13—C140.1 (3)
C4—C5—C6—C10.3 (4)C11—C12—C13—Cl1179.04 (17)
C2—C1—C6—C50.7 (3)C12—C13—C14—C150.5 (3)
C7—C1—C6—C5179.7 (2)Cl1—C13—C14—C15179.67 (17)
C6—C1—C7—C8112.2 (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—C14177.2 (2)
C1—C7—C8—C9175.36 (19)C3—C2—N1—O26.2 (3)
O3—C8—C9—O4115.7 (3)C1—C2—N1—O2174.8 (2)
C7—C8—C9—O459.3 (3)C3—C2—N1—O1169.5 (2)
O3—C8—C9—C1063.5 (3)C1—C2—N1—O19.5 (3)
C7—C8—C9—C10121.5 (2)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x+1, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC15H10ClNO4
Mr303.69
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)7.9995 (3), 6.3730 (2), 26.7750 (5)
β (°) 91.340 (2)
V3)1364.64 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.943, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
8762, 2408, 1872
Rint0.027
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.133, 1.07
No. of reflections2408
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.28

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
C2—N11.475 (3)C13—Cl11.734 (2)
C8—O31.195 (3)N1—O21.221 (3)
C8—C91.532 (3)N1—O11.229 (3)
C9—O41.213 (3)
C3—C2—N1116.1 (2)C7—C8—C9115.99 (19)
C1—C2—N1121.2 (2)O4—C9—C10123.5 (2)
C8—C7—C1114.60 (19)O4—C9—C8116.8 (2)
O3—C8—C7123.96 (19)C10—C9—C8119.63 (19)
O3—C8—C9119.84 (19)O2—N1—O1123.0 (2)
C1—C7—C8—O39.9 (3)O3—C8—C9—C1063.5 (3)
C1—C7—C8—C9175.36 (19)C7—C8—C9—C10121.5 (2)
O3—C8—C9—O4115.7 (3)O4—C9—C10—C15179.9 (2)
C7—C8—C9—O459.3 (3)O4—C9—C10—C112.6 (3)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x+1, y1/2, z+3/2.
 

Acknowledgements

The authors are grateful to Xiangfan University for financial support.

References

First citationBarnes, P. R. & Gist, L. A. (1950). J. Am. Chem. Soc. 72, 2509–2510.  CrossRef CAS Web of Science Google Scholar
First citationBruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLeusen, D. van & van Leusen, A. M. (1977). Tetrahedron Lett. 18, 4233–4236.  Google Scholar
First citationSaalfrank, R. W., Hafner, W., Markmann, J. & Bestmann, H. J. (1988). Tetrahedron, 44, 5095–5100.  CrossRef CAS Web of Science Google Scholar
First citationSchobert, R. (1988). Angew. Chem. Int. Ed. 27, 855–856.  CrossRef Google Scholar
First citationSheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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