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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1113.
Published online 2009 April 25. doi:  10.1107/S1600536809014676
PMCID: PMC2977789

(Z)-3-(9-Anthryl)-1-(4-chloro­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one

Abstract

In the title compound, C26H16ClN3O3, the dihedral angle between the anthracene mean plane and imidazole ring is 64.75 (2)°. In the crystal, π–π inter­actions between anthracene fragments lead to the formation of stacks of mol­ecules propagating in [100]. The short distance between the carbonyl groups of symmetry-related molecules [C(...)O = 2.985 (2) Å] indicates the existence of dipole–dipole inter­actions. The crystal packing also exhibits short inter­molecular contacts between the nitro groups and Cl atoms [Cl(...)O = 3.181 (2) Å].

Related literature

For general background, see: Corrêa et al. (2001 [triangle]); Daskiewicz et al. (2005 [triangle]); Sivakumar et al. (2009 [triangle]); Vogel et al. (2008 [triangle]). The synthesis was described by Erhardt et al. (1985 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1113-scheme1.jpg

Experimental

Crystal data

  • C26H16ClN3O3
  • M r = 453.87
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1113-efi1.jpg
  • a = 8.0511 (9) Å
  • b = 11.0406 (12) Å
  • c = 12.9274 (14) Å
  • α = 76.065 (2)°
  • β = 85.974 (2)°
  • γ = 71.258 (2)°
  • V = 1056.1 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 292 K
  • 0.16 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.956, T max = 0.979
  • 6168 measured reflections
  • 4070 independent reflections
  • 3354 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.113
  • S = 1.04
  • 4070 reflections
  • 299 parameters
  • H-atom parameters constrained
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Selected interatomic distances (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014676/cv2548sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014676/cv2548Isup2.hkl

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

Acknowledgments

We thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.

supplementary crystallographic information

Comment

Chalcones or 1,3-diaryl-2-propen-1-ones are natural or synthetic compounds belonging to the flavonoid family (Corrêa et al., 2001). They exhibit different kinds of biological activities, such as antimicrobial, anticancer, antiviral, ant-malarial, anti-inflammatory activities (Daskiewicz et al., 2005; Vogel et al., 2008; Sivakumar et al., 2009). Hence, chalcones are considered as a class of important therapeutic potentials. The title compound, (I), is part of our effort in order to contribute this research, and we report its crystal structure here.

In (I) (Fig. 1), the dihedral angle between the anthracene and imidazole rings is 64.75 (2)° and the nitroimidazole is slightly twisted away from the 4-chlorophenyl ring with a dihedral angle of 11.55 (2)°. In the crystal, the π-π interactions between the anthracene fragments (Table 1) lead to formation of stacks of the molecules propagated in direction [100]. The short distance between the carbonyl groups [C17···O1(1-x, 2-y, -z) 2.985 (2) Å] (Table 1) reveals an existence of dipole-dipole interactions. The crystal packing also exhibits short intermolecular contacts between the nitro groups and chlorine atoms [Cl···O 3.181 (2) Å] (Table 1).

Experimental

Compound (I) was synthesized according to the procedure of Erhardt et al. (1985). A crystal of (I) suitable for X-ray analysis was grown from a mixture solution of chloroform and acetone by slow evaporation at room temperature.

Refinement

All the hydrogen atoms were placed at their geometrical positions with C—H = 0.93Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

Crystal data

C26H16ClN3O3Z = 2
Mr = 453.87F(000) = 468
Triclinic, P1Dx = 1.427 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0511 (9) ÅCell parameters from 2837 reflections
b = 11.0406 (12) Åθ = 1.4–25.3°
c = 12.9274 (14) ŵ = 0.22 mm1
α = 76.065 (2)°T = 292 K
β = 85.974 (2)°Block, orange
γ = 71.258 (2)°0.16 × 0.12 × 0.10 mm
V = 1056.1 (2) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer4070 independent reflections
Radiation source: fine focus sealed Siemens Mo tube3354 reflections with I > 2σ(I)
graphiteRint = 0.014
0.3° wide ω exposures scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −9→9
Tmin = 0.956, Tmax = 0.979k = −13→10
6168 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.113w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4068P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4070 reflectionsΔρmax = 0.56 e Å3
299 parametersΔρmin = −0.50 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.138 (5)

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
C10.4503 (2)0.91044 (16)0.38505 (12)0.0381 (4)
C20.3150 (2)0.99845 (18)0.43057 (13)0.0427 (4)
C30.2324 (3)1.13103 (19)0.37653 (16)0.0532 (5)
H30.26731.16180.30780.064*
C40.1039 (3)1.2135 (2)0.4233 (2)0.0690 (6)
H40.05211.29990.38630.083*
C50.0482 (3)1.1702 (3)0.5267 (2)0.0758 (7)
H5−0.03891.22840.55810.091*
C60.1195 (3)1.0455 (3)0.58072 (18)0.0671 (6)
H60.08061.01810.64910.080*
C70.2544 (2)0.9537 (2)0.53486 (14)0.0507 (5)
C80.3284 (3)0.8240 (2)0.58804 (14)0.0570 (5)
H80.28700.79480.65530.068*
C90.4618 (3)0.7360 (2)0.54475 (14)0.0528 (5)
C100.5404 (4)0.6035 (2)0.60138 (18)0.0751 (7)
H100.49810.57390.66820.090*
C110.6738 (4)0.5211 (2)0.5604 (2)0.0864 (8)
H110.72100.43450.59830.104*
C120.7438 (4)0.5643 (2)0.45999 (19)0.0730 (7)
H120.83850.50650.43320.088*
C130.6736 (3)0.68926 (18)0.40237 (15)0.0516 (5)
H130.72180.71640.33680.062*
C140.5276 (2)0.77936 (17)0.44076 (13)0.0428 (4)
C150.5225 (2)0.96316 (15)0.28220 (12)0.0370 (4)
H150.56051.03480.28040.044*
C160.5410 (2)0.92308 (15)0.19171 (12)0.0351 (4)
C170.6425 (2)0.97302 (15)0.10011 (12)0.0364 (4)
C180.6982 (2)1.08892 (16)0.10310 (12)0.0372 (4)
C190.5813 (2)1.21059 (17)0.10958 (14)0.0442 (4)
H190.46151.22270.11220.053*
C200.6414 (3)1.31410 (18)0.11219 (15)0.0503 (5)
H200.56311.39610.11530.060*
C210.8197 (3)1.29305 (19)0.11011 (15)0.0532 (5)
C220.9379 (3)1.1743 (2)0.10195 (16)0.0563 (5)
H221.05761.16260.09950.068*
C230.8762 (2)1.07254 (18)0.09746 (15)0.0474 (4)
H230.95500.99220.09060.057*
C240.5604 (3)0.70649 (17)0.15237 (15)0.0488 (4)
H240.67910.68120.13600.059*
C250.2993 (3)0.70981 (18)0.17933 (14)0.0480 (4)
C260.3024 (2)0.82478 (17)0.19785 (13)0.0425 (4)
H260.20980.89020.21830.051*
Cl10.90255 (10)1.41713 (6)0.11994 (6)0.0886 (3)
N10.47212 (18)0.82266 (13)0.17975 (10)0.0378 (3)
N20.4588 (2)0.63534 (15)0.15188 (13)0.0554 (4)
N30.1473 (3)0.6670 (2)0.18554 (14)0.0685 (5)
O10.68863 (17)0.91581 (12)0.02841 (10)0.0486 (3)
O20.0083 (3)0.7406 (2)0.21193 (17)0.0925 (6)
O30.1648 (3)0.5612 (2)0.16539 (18)0.1061 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0429 (9)0.0474 (9)0.0326 (8)−0.0239 (7)−0.0008 (7)−0.0116 (7)
C20.0408 (9)0.0578 (11)0.0399 (9)−0.0234 (8)0.0005 (7)−0.0200 (8)
C30.0511 (11)0.0579 (12)0.0554 (11)−0.0168 (9)−0.0008 (9)−0.0223 (9)
C40.0561 (13)0.0703 (14)0.0842 (16)−0.0094 (11)−0.0040 (11)−0.0377 (13)
C50.0495 (13)0.108 (2)0.0832 (17)−0.0176 (13)0.0071 (11)−0.0576 (16)
C60.0482 (12)0.119 (2)0.0535 (12)−0.0369 (13)0.0112 (9)−0.0440 (13)
C70.0441 (10)0.0823 (14)0.0407 (9)−0.0335 (10)0.0028 (8)−0.0241 (10)
C80.0605 (12)0.0901 (16)0.0345 (9)−0.0445 (12)0.0046 (8)−0.0135 (10)
C90.0681 (13)0.0633 (12)0.0366 (9)−0.0377 (10)−0.0063 (8)−0.0040 (8)
C100.113 (2)0.0690 (15)0.0459 (12)−0.0430 (15)−0.0093 (12)0.0035 (11)
C110.137 (3)0.0527 (13)0.0578 (14)−0.0232 (15)−0.0204 (15)0.0063 (11)
C120.0934 (18)0.0528 (12)0.0627 (14)−0.0081 (12)−0.0162 (12)−0.0099 (10)
C130.0619 (12)0.0490 (10)0.0441 (10)−0.0177 (9)−0.0071 (9)−0.0085 (8)
C140.0505 (10)0.0486 (10)0.0365 (9)−0.0249 (8)−0.0043 (7)−0.0089 (7)
C150.0408 (9)0.0366 (8)0.0385 (8)−0.0177 (7)−0.0019 (7)−0.0091 (7)
C160.0384 (9)0.0322 (8)0.0376 (8)−0.0142 (6)−0.0030 (6)−0.0083 (6)
C170.0361 (8)0.0373 (8)0.0358 (8)−0.0104 (7)−0.0018 (6)−0.0092 (7)
C180.0439 (9)0.0390 (8)0.0318 (8)−0.0178 (7)0.0038 (6)−0.0080 (6)
C190.0456 (10)0.0416 (9)0.0458 (9)−0.0154 (8)0.0034 (7)−0.0092 (7)
C200.0647 (12)0.0386 (9)0.0493 (10)−0.0194 (8)0.0072 (9)−0.0107 (8)
C210.0713 (13)0.0516 (11)0.0508 (11)−0.0378 (10)0.0146 (9)−0.0169 (9)
C220.0508 (11)0.0676 (13)0.0648 (12)−0.0333 (10)0.0149 (9)−0.0256 (10)
C230.0452 (10)0.0499 (10)0.0526 (10)−0.0186 (8)0.0091 (8)−0.0195 (8)
C240.0616 (12)0.0385 (9)0.0507 (10)−0.0185 (8)0.0026 (8)−0.0152 (8)
C250.0647 (12)0.0497 (10)0.0391 (9)−0.0343 (9)−0.0065 (8)−0.0038 (8)
C260.0461 (10)0.0467 (9)0.0402 (9)−0.0221 (8)−0.0022 (7)−0.0089 (7)
Cl10.1041 (5)0.0745 (4)0.1183 (6)−0.0626 (4)0.0236 (4)−0.0392 (4)
N10.0449 (8)0.0364 (7)0.0372 (7)−0.0181 (6)−0.0005 (6)−0.0107 (6)
N20.0803 (12)0.0435 (9)0.0524 (9)−0.0313 (8)−0.0009 (8)−0.0133 (7)
N30.0902 (15)0.0785 (13)0.0566 (10)−0.0601 (12)−0.0108 (10)−0.0030 (9)
O10.0552 (8)0.0524 (7)0.0465 (7)−0.0217 (6)0.0111 (6)−0.0232 (6)
O20.0715 (12)0.1073 (15)0.1141 (15)−0.0560 (11)0.0001 (11)−0.0155 (12)
O30.1425 (18)0.1018 (14)0.1193 (16)−0.0927 (14)−0.0026 (13)−0.0342 (12)

Geometric parameters (Å, °)

C1—C21.408 (2)C15—H150.9300
C1—C141.408 (2)C16—N11.4318 (19)
C1—C151.477 (2)C16—C171.488 (2)
C2—C31.421 (3)C17—O11.2162 (19)
C2—C71.429 (2)C17—C181.495 (2)
C3—C41.355 (3)C18—C231.384 (2)
C3—H30.9300C18—C191.389 (2)
C4—C51.402 (4)C19—C201.384 (2)
C4—H40.9300C19—H190.9300
C5—C61.341 (4)C20—C211.378 (3)
C5—H50.9300C20—H200.9300
C6—C71.432 (3)C21—C221.374 (3)
C6—H60.9300C21—Cl11.7382 (18)
C7—C81.384 (3)C22—C231.380 (3)
C8—C91.385 (3)C22—H220.9300
C8—H80.9300C23—H230.9300
C9—C101.425 (3)C24—N21.305 (2)
C9—C141.439 (2)C24—N11.369 (2)
C10—C111.336 (4)C24—H240.9300
C10—H100.9300C25—C261.355 (2)
C11—C121.415 (4)C25—N21.360 (3)
C11—H110.9300C25—N31.437 (3)
C12—C131.357 (3)C26—N11.364 (2)
C12—H120.9300C26—H260.9300
C13—C141.422 (3)N3—O31.219 (3)
C13—H130.9300N3—O21.235 (3)
C15—C161.330 (2)
C17···O1i2.985 (2)Cg1···Cg2iii3.746 (7)
Cl1···O3ii3.181 (3)Cg2···Cg2iv3.863 (8)
C2—C1—C14121.15 (15)C16—C15—H15115.3
C2—C1—C15117.97 (15)C1—C15—H15115.3
C14—C1—C15120.54 (15)C15—C16—N1121.23 (14)
C1—C2—C3122.84 (16)C15—C16—C17122.54 (14)
C1—C2—C7119.41 (17)N1—C16—C17116.12 (13)
C3—C2—C7117.74 (17)O1—C17—C16120.77 (14)
C4—C3—C2121.3 (2)O1—C17—C18120.97 (14)
C4—C3—H3119.4C16—C17—C18118.09 (13)
C2—C3—H3119.4C23—C18—C19119.23 (15)
C3—C4—C5120.8 (2)C23—C18—C17117.30 (15)
C3—C4—H4119.6C19—C18—C17123.47 (15)
C5—C4—H4119.6C20—C19—C18120.67 (17)
C6—C5—C4120.4 (2)C20—C19—H19119.7
C6—C5—H5119.8C18—C19—H19119.7
C4—C5—H5119.8C21—C20—C19118.55 (17)
C5—C6—C7121.2 (2)C21—C20—H20120.7
C5—C6—H6119.4C19—C20—H20120.7
C7—C6—H6119.4C22—C21—C20121.89 (17)
C8—C7—C2119.04 (17)C22—C21—Cl1117.65 (16)
C8—C7—C6122.40 (19)C20—C21—Cl1120.45 (15)
C2—C7—C6118.6 (2)C21—C22—C23118.98 (18)
C7—C8—C9122.41 (17)C21—C22—H22120.5
C7—C8—H8118.8C23—C22—H22120.5
C9—C8—H8118.8C22—C23—C18120.63 (17)
C8—C9—C10121.97 (19)C22—C23—H23119.7
C8—C9—C14119.60 (18)C18—C23—H23119.7
C10—C9—C14118.4 (2)N2—C24—N1112.21 (18)
C11—C10—C9121.4 (2)N2—C24—H24123.9
C11—C10—H10119.3N1—C24—H24123.9
C9—C10—H10119.3C26—C25—N2112.81 (16)
C10—C11—C12120.6 (2)C26—C25—N3125.7 (2)
C10—C11—H11119.7N2—C25—N3121.48 (18)
C12—C11—H11119.7C25—C26—N1104.26 (16)
C13—C12—C11120.5 (2)C25—C26—H26127.9
C13—C12—H12119.7N1—C26—H26127.9
C11—C12—H12119.7C26—N1—C24106.95 (14)
C12—C13—C14121.0 (2)C26—N1—C16125.02 (14)
C12—C13—H13119.5C24—N1—C16128.00 (15)
C14—C13—H13119.5C24—N2—C25103.77 (15)
C1—C14—C13123.55 (16)O3—N3—O2124.9 (2)
C1—C14—C9118.36 (17)O3—N3—C25118.1 (2)
C13—C14—C9118.00 (17)O2—N3—C25116.95 (19)
C16—C15—C1129.36 (14)
C14—C1—C2—C3−179.34 (15)C1—C15—C16—C17−169.86 (16)
C15—C1—C2—C37.3 (2)C15—C16—C17—O1164.24 (16)
C14—C1—C2—C7−0.4 (2)N1—C16—C17—O1−12.1 (2)
C15—C1—C2—C7−173.69 (14)C15—C16—C17—C18−11.0 (2)
C1—C2—C3—C4−179.21 (18)N1—C16—C17—C18172.64 (13)
C7—C2—C3—C41.8 (3)O1—C17—C18—C23−54.0 (2)
C2—C3—C4—C5−0.1 (3)C16—C17—C18—C23121.27 (17)
C3—C4—C5—C6−1.0 (3)O1—C17—C18—C19125.09 (18)
C4—C5—C6—C70.4 (3)C16—C17—C18—C19−59.7 (2)
C1—C2—C7—C8−1.1 (2)C23—C18—C19—C20−1.1 (3)
C3—C2—C7—C8177.93 (16)C17—C18—C19—C20179.92 (15)
C1—C2—C7—C6178.61 (15)C18—C19—C20—C21−1.1 (3)
C3—C2—C7—C6−2.3 (2)C19—C20—C21—C222.2 (3)
C5—C6—C7—C8−178.96 (19)C19—C20—C21—Cl1−176.77 (14)
C5—C6—C7—C21.3 (3)C20—C21—C22—C23−1.1 (3)
C2—C7—C8—C91.3 (3)Cl1—C21—C22—C23177.95 (15)
C6—C7—C8—C9−178.43 (17)C21—C22—C23—C18−1.2 (3)
C7—C8—C9—C10178.23 (19)C19—C18—C23—C222.2 (3)
C7—C8—C9—C140.0 (3)C17—C18—C23—C22−178.67 (16)
C8—C9—C10—C11−177.3 (2)N2—C25—C26—N10.8 (2)
C14—C9—C10—C110.9 (3)N3—C25—C26—N1−178.49 (16)
C9—C10—C11—C121.5 (4)C25—C26—N1—C24−0.45 (18)
C10—C11—C12—C13−1.7 (4)C25—C26—N1—C16−178.48 (14)
C11—C12—C13—C14−0.6 (3)N2—C24—N1—C260.0 (2)
C2—C1—C14—C13−174.85 (16)N2—C24—N1—C16177.96 (15)
C15—C1—C14—C13−1.7 (2)C15—C16—N1—C2653.9 (2)
C2—C1—C14—C91.6 (2)C17—C16—N1—C26−129.70 (16)
C15—C1—C14—C9174.79 (14)C15—C16—N1—C24−123.73 (19)
C12—C13—C14—C1179.44 (18)C17—C16—N1—C2452.7 (2)
C12—C13—C14—C93.0 (3)N1—C24—N2—C250.4 (2)
C8—C9—C14—C1−1.5 (2)C26—C25—N2—C24−0.8 (2)
C10—C9—C14—C1−179.75 (17)N3—C25—N2—C24178.53 (16)
C8—C9—C14—C13175.20 (17)C26—C25—N3—O3179.18 (19)
C10—C9—C14—C13−3.1 (3)N2—C25—N3—O30.0 (3)
C2—C1—C15—C16−126.63 (19)C26—C25—N3—O2−1.4 (3)
C14—C1—C15—C1660.0 (2)N2—C25—N3—O2179.44 (19)
C1—C15—C16—N16.3 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2548).

References

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