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 November 1; 65(Pt 11): o2619.
Published online 2009 October 3. doi:  10.1107/S1600536809039221
PMCID: PMC2971385

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

Abstract

In the title mol­ecule, C27H19N3O3, the imidazole and benzene rings make dihedral angles of 64.72 (4) and 64.02 (4)°, respectively, with the anthracene ring system (r.m.s. deviation = 0.043 Å). The nitro group is coplanar with the imidazole ring [dihedral angle = 1.1 (1)°]. The crystal packing is stabilized by weak π–π inter­actions with centroid–centroid distances of 3.7342 (10) and 3.7627 (9) Å.

Related literature

For the crystal structures of the chloro and bromo analogues, see: Wang et al. (2009 [triangle]); Lu et al. (2009 [triangle]). For general background to chalcones, see: Vogel et al. (2008 [triangle]). For the synthesis, see: Erhardt et al. (1985 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2619-scheme1.jpg

Experimental

Crystal data

  • C27H19N3O3
  • M r = 433.45
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2619-efi1.jpg
  • a = 7.9335 (9) Å
  • b = 11.2626 (13) Å
  • c = 13.0291 (15) Å
  • α = 75.454 (2)°
  • β = 85.763 (2)°
  • γ = 71.059 (2)°
  • V = 1065.8 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.36 × 0.23 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.968, T max = 0.991
  • 12116 measured reflections
  • 4621 independent reflections
  • 3646 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.127
  • S = 1.05
  • 4621 reflections
  • 299 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039221/ci2921sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039221/ci2921Isup2.hkl

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

Acknowledgments

The authors 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 (Vogel et al., 2008). They exhibit diverse kinds of biological activities. Hence, chalcones are considered as an important class of therapeutic agents. A series of chalcone derivatives containing a imidazole ring have been synthesized in our lab and crystal structues of some of them have been reported (Lu et al., 2009; Wang et al., 2009). We report here the crystal structure of the title compound.

In the molecular structure of the title compound (Fig. 1), the imidazole and benzene ring of the tolyl group form dihedral angles of 64.72 (4)° and 64.02 (4)°, respectively, with the anthracene ring system (r.m.s. deviation 0.043 Å). The nitro group is coplanar with the imidazole ring [dihedral angle 1.1 (1)°].

The crystal structure is stabilized by weak π-π interactions between imidazole and benzene ring of the tolyl group (centroid to centroid distance = 3.7627 (9) Å) and those between the rings of the anthracene ring system (centroid to centroid distance = 3.7342 (10) Å).

Experimental

The title compound was synthesized according to the procedure of Erhardt et al. (1985). Single crystals suitable for X-ray analysis was grown from a chloroform solution by slow evaporation at room temperature.

Refinement

H atoms were placed at calculated positions with C-H = 0.93 Å (aromatic) and 0.96 Å (methyl). The Uiso(H) values were set equal to 1.2Ueq(Caromatic) and 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C27H19N3O3Z = 2
Mr = 433.45F(000) = 452
Triclinic, P1Dx = 1.351 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9335 (9) ÅCell parameters from 5053 reflections
b = 11.2626 (13) Åθ = 2.2–28.1°
c = 13.0291 (15) ŵ = 0.09 mm1
α = 75.454 (2)°T = 298 K
β = 85.763 (2)°Plate, yellow
γ = 71.059 (2)°0.36 × 0.23 × 0.10 mm
V = 1065.8 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer4621 independent reflections
Radiation source: fine-focus sealed tube3646 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)h = −10→10
Tmin = 0.968, Tmax = 0.991k = −14→14
12116 measured reflectionsl = −16→16

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0696P)2 + 0.061P] where P = (Fo2 + 2Fc2)/3
4621 reflections(Δ/σ)max = 0.012
299 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.23 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
C10.8022 (2)0.80103 (14)0.10371 (11)0.0625 (4)
C20.9235 (2)0.68461 (16)0.09495 (12)0.0655 (4)
H21.04430.67600.08950.079*
C30.86855 (18)0.58070 (13)0.09409 (10)0.0542 (3)
H30.95210.50320.08710.065*
C40.68960 (16)0.59098 (11)0.10360 (9)0.0443 (3)
C50.56700 (18)0.70796 (12)0.11149 (10)0.0525 (3)
H50.44640.71640.11760.063*
C60.6231 (2)0.81227 (13)0.11031 (11)0.0604 (4)
H60.53940.89110.11400.073*
C70.8646 (3)0.91345 (19)0.10604 (18)0.1030 (7)
H7A0.98840.89380.08780.155*
H7B0.84860.92880.17590.155*
H7C0.79640.98930.05590.155*
C80.63944 (15)0.47439 (11)0.10306 (9)0.0429 (3)
C90.53578 (15)0.42485 (10)0.19465 (9)0.0401 (3)
C100.51789 (15)0.46279 (11)0.28466 (9)0.0424 (3)
H100.55670.53290.28250.051*
C110.55904 (19)0.21206 (12)0.15682 (10)0.0547 (3)
H110.68000.18790.14130.066*
C120.29544 (19)0.21363 (13)0.18201 (9)0.0522 (3)
C130.29627 (17)0.32641 (12)0.20011 (9)0.0479 (3)
H130.20100.39020.21980.057*
C140.44576 (16)0.41062 (12)0.38765 (9)0.0442 (3)
C150.31154 (16)0.49758 (13)0.43426 (9)0.0497 (3)
C160.23060 (19)0.62857 (14)0.38169 (12)0.0604 (4)
H160.26490.65930.31300.072*
C170.1035 (2)0.71059 (18)0.42967 (15)0.0772 (5)
H170.05280.79650.39360.093*
C180.0482 (2)0.6666 (2)0.53315 (16)0.0844 (6)
H18−0.03770.72380.56550.101*
C190.1187 (2)0.5429 (2)0.58552 (13)0.0770 (5)
H190.07990.51520.65380.092*
C200.25212 (18)0.45250 (17)0.53893 (10)0.0587 (4)
C210.3253 (2)0.32471 (18)0.59118 (10)0.0668 (4)
H210.28430.29580.65850.080*
C220.4581 (2)0.23721 (15)0.54715 (10)0.0609 (4)
C230.5358 (3)0.10705 (19)0.60296 (13)0.0849 (5)
H230.49340.07760.66980.102*
C240.6697 (3)0.02531 (18)0.56107 (15)0.0961 (6)
H240.7168−0.06040.59830.115*
C250.7395 (3)0.06850 (16)0.46106 (13)0.0800 (5)
H250.83460.01160.43390.096*
C260.6691 (2)0.19203 (13)0.40416 (11)0.0588 (4)
H260.71750.21900.33860.071*
C270.52314 (18)0.28088 (13)0.44281 (9)0.0495 (3)
N10.46726 (13)0.32578 (9)0.18306 (7)0.0428 (2)
N20.45809 (17)0.14128 (11)0.15594 (9)0.0602 (3)
N40.1423 (2)0.17060 (15)0.18753 (10)0.0718 (4)
O10.69016 (12)0.41643 (9)0.03388 (7)0.0576 (3)
O20.1606 (2)0.06711 (14)0.16772 (11)0.1051 (5)
O30.00028 (18)0.24220 (15)0.21342 (12)0.0975 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0851 (10)0.0617 (9)0.0534 (8)−0.0413 (8)0.0181 (7)−0.0175 (7)
C20.0631 (9)0.0805 (10)0.0669 (9)−0.0393 (8)0.0181 (7)−0.0256 (8)
C30.0561 (8)0.0585 (8)0.0523 (7)−0.0224 (6)0.0110 (6)−0.0185 (6)
C40.0526 (7)0.0487 (7)0.0330 (6)−0.0207 (5)0.0039 (5)−0.0070 (5)
C50.0549 (7)0.0518 (7)0.0487 (7)−0.0175 (6)0.0043 (6)−0.0088 (6)
C60.0793 (10)0.0476 (7)0.0520 (8)−0.0192 (7)0.0090 (7)−0.0113 (6)
C70.1274 (17)0.0883 (13)0.1247 (16)−0.0694 (13)0.0351 (14)−0.0441 (12)
C80.0430 (6)0.0459 (6)0.0378 (6)−0.0122 (5)−0.0015 (5)−0.0083 (5)
C90.0436 (6)0.0390 (6)0.0385 (6)−0.0150 (5)−0.0023 (5)−0.0078 (5)
C100.0473 (6)0.0432 (6)0.0399 (6)−0.0189 (5)−0.0012 (5)−0.0094 (5)
C110.0663 (8)0.0466 (7)0.0539 (7)−0.0195 (6)0.0048 (6)−0.0160 (6)
C120.0684 (9)0.0562 (8)0.0393 (6)−0.0335 (7)−0.0051 (6)−0.0049 (5)
C130.0509 (7)0.0533 (7)0.0419 (6)−0.0211 (6)−0.0030 (5)−0.0089 (5)
C140.0501 (7)0.0566 (7)0.0347 (6)−0.0276 (6)−0.0006 (5)−0.0122 (5)
C150.0491 (7)0.0693 (9)0.0428 (6)−0.0290 (6)0.0004 (5)−0.0216 (6)
C160.0582 (8)0.0705 (9)0.0604 (8)−0.0221 (7)0.0010 (6)−0.0276 (7)
C170.0632 (9)0.0857 (11)0.0916 (12)−0.0160 (8)−0.0031 (8)−0.0463 (10)
C180.0562 (9)0.1257 (17)0.0902 (13)−0.0252 (10)0.0098 (9)−0.0667 (13)
C190.0564 (9)0.1382 (17)0.0592 (9)−0.0450 (10)0.0129 (7)−0.0491 (11)
C200.0508 (7)0.0984 (11)0.0442 (7)−0.0399 (7)0.0042 (6)−0.0274 (7)
C210.0708 (9)0.1096 (13)0.0367 (7)−0.0552 (9)0.0048 (6)−0.0134 (8)
C220.0771 (10)0.0761 (9)0.0401 (7)−0.0446 (8)−0.0072 (6)−0.0034 (6)
C230.1265 (16)0.0850 (12)0.0485 (8)−0.0569 (12)−0.0116 (9)0.0089 (8)
C240.151 (2)0.0634 (10)0.0639 (11)−0.0333 (12)−0.0260 (12)0.0091 (9)
C250.1040 (13)0.0594 (9)0.0676 (10)−0.0148 (9)−0.0201 (9)−0.0081 (8)
C260.0715 (9)0.0565 (8)0.0480 (7)−0.0221 (7)−0.0097 (6)−0.0065 (6)
C270.0603 (8)0.0576 (8)0.0378 (6)−0.0308 (6)−0.0062 (5)−0.0065 (5)
N10.0501 (6)0.0427 (5)0.0385 (5)−0.0179 (4)−0.0008 (4)−0.0105 (4)
N20.0837 (9)0.0513 (6)0.0546 (7)−0.0321 (6)0.0017 (6)−0.0150 (5)
N40.0921 (10)0.0831 (9)0.0569 (7)−0.0572 (9)−0.0091 (7)−0.0046 (7)
O10.0656 (6)0.0654 (6)0.0495 (5)−0.0253 (5)0.0130 (4)−0.0253 (5)
O20.1427 (12)0.1039 (10)0.1091 (10)−0.0885 (10)−0.0031 (9)−0.0309 (8)
O30.0747 (8)0.1167 (11)0.1149 (11)−0.0555 (8)0.0020 (7)−0.0195 (8)

Geometric parameters (Å, °)

C1—C21.378 (2)C13—H130.93
C1—C61.383 (2)C14—C271.4085 (18)
C1—C71.509 (2)C14—C151.4099 (17)
C2—C31.3779 (19)C15—C161.414 (2)
C2—H20.93C15—C201.4327 (18)
C3—C41.3852 (18)C16—C171.361 (2)
C3—H30.93C16—H160.93
C4—C51.3835 (18)C17—C181.405 (3)
C4—C81.4923 (16)C17—H170.93
C5—C61.3814 (18)C18—C191.339 (3)
C5—H50.93C18—H180.93
C6—H60.93C19—C201.429 (2)
C7—H7A0.96C19—H190.93
C7—H7B0.96C20—C211.377 (2)
C7—H7C0.96C21—C221.390 (2)
C8—O11.2133 (13)C21—H210.93
C8—C91.4933 (16)C22—C231.415 (2)
C9—C101.3289 (15)C22—C271.4426 (18)
C9—N11.4332 (14)C23—C241.344 (3)
C10—C141.4772 (15)C23—H230.93
C10—H100.93C24—C251.411 (3)
C11—N21.3029 (17)C24—H240.93
C11—N11.3657 (16)C25—C261.355 (2)
C11—H110.93C25—H250.93
C12—C131.3510 (17)C26—C271.418 (2)
C12—N21.3551 (18)C26—H260.93
C12—N41.4381 (18)N4—O21.2174 (17)
C13—N11.3563 (15)N4—O31.2346 (18)
C2—C1—C6118.62 (13)C14—C15—C20119.28 (13)
C2—C1—C7120.37 (15)C16—C15—C20117.91 (12)
C6—C1—C7121.01 (15)C17—C16—C15121.32 (15)
C1—C2—C3120.94 (14)C17—C16—H16119.3
C1—C2—H2119.5C15—C16—H16119.3
C3—C2—H2119.5C16—C17—C18120.57 (18)
C2—C3—C4120.40 (13)C16—C17—H17119.7
C2—C3—H3119.8C18—C17—H17119.7
C4—C3—H3119.8C19—C18—C17120.34 (16)
C5—C4—C3118.92 (12)C19—C18—H18119.8
C5—C4—C8123.45 (11)C17—C18—H18119.8
C3—C4—C8117.62 (11)C18—C19—C20121.48 (16)
C6—C5—C4120.24 (13)C18—C19—H19119.3
C6—C5—H5119.9C20—C19—H19119.3
C4—C5—H5119.9C21—C20—C19122.36 (14)
C5—C6—C1120.85 (13)C21—C20—C15119.29 (13)
C5—C6—H6119.6C19—C20—C15118.35 (15)
C1—C6—H6119.6C20—C21—C22122.53 (12)
C1—C7—H7A109.5C20—C21—H21118.7
C1—C7—H7B109.5C22—C21—H21118.7
H7A—C7—H7B109.5C21—C22—C23121.93 (14)
C1—C7—H7C109.5C21—C22—C27119.26 (13)
H7A—C7—H7C109.5C23—C22—C27118.78 (16)
H7B—C7—H7C109.5C24—C23—C22121.12 (16)
O1—C8—C4121.31 (10)C24—C23—H23119.4
O1—C8—C9120.52 (11)C22—C23—H23119.4
C4—C8—C9118.02 (10)C23—C24—C25120.55 (16)
C10—C9—N1121.36 (10)C23—C24—H24119.7
C10—C9—C8122.61 (10)C25—C24—H24119.7
N1—C9—C8115.87 (9)C26—C25—C24120.61 (18)
C9—C10—C14129.89 (10)C26—C25—H25119.7
C9—C10—H10115.1C24—C25—H25119.7
C14—C10—H10115.1C25—C26—C27121.12 (14)
N2—C11—N1112.40 (13)C25—C26—H26119.4
N2—C11—H11123.8C27—C26—H26119.4
N1—C11—H11123.8C14—C27—C26123.60 (11)
C13—C12—N2112.85 (11)C14—C27—C22118.59 (13)
C13—C12—N4125.76 (14)C26—C27—C22117.70 (12)
N2—C12—N4121.39 (13)C13—N1—C11106.73 (10)
C12—C13—N1104.50 (11)C13—N1—C9125.53 (10)
C12—C13—H13127.7C11—N1—C9127.71 (11)
N1—C13—H13127.7C11—N2—C12103.51 (11)
C27—C14—C15121.01 (11)O2—N4—O3124.53 (15)
C27—C14—C10120.56 (11)O2—N4—C12118.72 (16)
C15—C14—C10118.04 (11)O3—N4—C12116.74 (13)
C14—C15—C16122.80 (11)
C6—C1—C2—C3−0.8 (2)C14—C15—C20—C19178.69 (11)
C7—C1—C2—C3179.16 (15)C16—C15—C20—C19−1.83 (17)
C1—C2—C3—C4−0.9 (2)C19—C20—C21—C22−178.42 (12)
C2—C3—C4—C51.47 (19)C15—C20—C21—C221.3 (2)
C2—C3—C4—C8−179.46 (11)C20—C21—C22—C23178.14 (14)
C3—C4—C5—C6−0.28 (18)C20—C21—C22—C270.1 (2)
C8—C4—C5—C6−179.29 (11)C21—C22—C23—C24−176.94 (16)
C4—C5—C6—C1−1.5 (2)C27—C22—C23—C241.1 (3)
C2—C1—C6—C52.0 (2)C22—C23—C24—C251.6 (3)
C7—C1—C6—C5−177.96 (14)C23—C24—C25—C26−2.0 (3)
C5—C4—C8—O1127.74 (13)C24—C25—C26—C27−0.5 (2)
C3—C4—C8—O1−51.28 (16)C15—C14—C27—C26−174.16 (11)
C5—C4—C8—C9−56.71 (15)C10—C14—C27—C26−1.40 (18)
C3—C4—C8—C9124.27 (12)C15—C14—C27—C222.01 (17)
O1—C8—C9—C10161.69 (12)C10—C14—C27—C22174.76 (11)
C4—C8—C9—C10−13.90 (17)C25—C26—C27—C14179.39 (13)
O1—C8—C9—N1−13.70 (16)C25—C26—C27—C223.2 (2)
C4—C8—C9—N1170.72 (10)C21—C22—C27—C14−1.75 (18)
N1—C9—C10—C145.68 (19)C23—C22—C27—C14−179.84 (13)
C8—C9—C10—C14−169.46 (11)C21—C22—C27—C26174.64 (12)
N2—C12—C13—N10.92 (14)C23—C22—C27—C26−3.45 (19)
N4—C12—C13—N1−178.45 (11)C12—C13—N1—C11−0.61 (13)
C9—C10—C14—C2759.15 (18)C12—C13—N1—C9−178.63 (10)
C9—C10—C14—C15−127.88 (14)N2—C11—N1—C130.13 (14)
C27—C14—C15—C16179.91 (11)N2—C11—N1—C9178.09 (10)
C10—C14—C15—C166.98 (17)C10—C9—N1—C1354.97 (16)
C27—C14—C15—C20−0.64 (17)C8—C9—N1—C13−129.58 (11)
C10—C14—C15—C20−173.57 (10)C10—C9—N1—C11−122.63 (14)
C14—C15—C16—C17−178.85 (12)C8—C9—N1—C1152.83 (15)
C20—C15—C16—C171.70 (19)N1—C11—N2—C120.41 (14)
C15—C16—C17—C18−0.4 (2)C13—C12—N2—C11−0.83 (14)
C16—C17—C18—C19−0.7 (2)N4—C12—N2—C11178.56 (11)
C17—C18—C19—C200.5 (2)C13—C12—N4—O2178.97 (13)
C18—C19—C20—C21−179.54 (14)N2—C12—N4—O2−0.34 (19)
C18—C19—C20—C150.8 (2)C13—C12—N4—O3−1.7 (2)
C14—C15—C20—C21−1.03 (17)N2—C12—N4—O3178.98 (13)
C16—C15—C20—C21178.45 (12)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2921).

References

  • Bruker (2001). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Erhardt, H., Mildenberger, H., Handte, R., Sachse, B., Hartz, P. & Bürstell, H. (1985). German Patent No. DE3406908.
  • Lu, Y.-H., Wang, G.-Z., Zhou, C.-H. & Zhang, Y.-Y. (2009). Acta Cryst. E65, o1396. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1997). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Vogel, S., Ohmayer, S., Brunner, G. & Heilmann, J. (2008). Bioorg. Med. Chem.16, 4286–4293. [PubMed]
  • Wang, G., Lu, Y., Zhou, C. & Zhang, Y. (2009). Acta Cryst. E65, o1113. [PMC free article] [PubMed]

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