Acta Cryst. (2009). E65, o2619 [ doi:10.1107/S1600536809039221 ]
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 ![[pi]](/logos/entities/pi_rmgif.gif)
- interactions with centroid-centroid distances of 3.7342 (10) and 3.7627 (9) Å.
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.
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).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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).
![[Figure 1]](./ci2921fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
| C27H19N3O3 | Z = 2 |
| Mr = 433.45 | F(000) = 452 |
| Triclinic, P1 | Dx = 1.351 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.9335 (9) Å | Cell parameters from 5053 reflections |
| b = 11.2626 (13) Å | θ = 2.2–28.1° |
| c = 13.0291 (15) Å | µ = 0.09 mm−1 |
| 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 |
| Bruker SMART CCD area-detector diffractometer | 4621 independent reflections |
| Radiation source: fine-focus sealed tube | 3646 reflections with I > 2σ(I) |
| graphite | Rint = 0.030 |
| φ and ω scans | θmax = 27.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −10→10 |
| Tmin = 0.968, Tmax = 0.991 | k = −14→14 |
| 12116 measured reflections | l = −16→16 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.127 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0696P)2 + 0.061P] where P = (Fo2 + 2Fc2)/3 |
| 4621 reflections | (Δ/σ)max = 0.012 |
| 299 parameters | Δρmax = 0.18 e Å−3 |
| 0 restraints | Δρmin = −0.23 e Å−3 |
| C27H19N3O3 | γ = 71.059 (2)° |
| Mr = 433.45 | V = 1065.8 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.9335 (9) Å | Mo Kα radiation |
| b = 11.2626 (13) Å | µ = 0.09 mm−1 |
| c = 13.0291 (15) Å | T = 298 K |
| α = 75.454 (2)° | 0.36 × 0.23 × 0.10 mm |
| β = 85.763 (2)° |
| Bruker SMART CCD area-detector diffractometer | 4621 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 3646 reflections with I > 2σ(I) |
| Tmin = 0.968, Tmax = 0.991 | Rint = 0.030 |
| 12116 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
| wR(F2) = 0.127 | Δρmax = 0.18 e Å−3 |
| S = 1.05 | Δρmin = −0.23 e Å−3 |
| 4621 reflections | Absolute structure: ? |
| 299 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.8022 (2) | 0.80103 (14) | 0.10371 (11) | 0.0625 (4) | |
| C2 | 0.9235 (2) | 0.68461 (16) | 0.09495 (12) | 0.0655 (4) | |
| H2 | 1.0443 | 0.6760 | 0.0895 | 0.079* | |
| C3 | 0.86855 (18) | 0.58070 (13) | 0.09409 (10) | 0.0542 (3) | |
| H3 | 0.9521 | 0.5032 | 0.0871 | 0.065* | |
| C4 | 0.68960 (16) | 0.59098 (11) | 0.10360 (9) | 0.0443 (3) | |
| C5 | 0.56700 (18) | 0.70796 (12) | 0.11149 (10) | 0.0525 (3) | |
| H5 | 0.4464 | 0.7164 | 0.1176 | 0.063* | |
| C6 | 0.6231 (2) | 0.81227 (13) | 0.11031 (11) | 0.0604 (4) | |
| H6 | 0.5394 | 0.8911 | 0.1140 | 0.073* | |
| C7 | 0.8646 (3) | 0.91345 (19) | 0.10604 (18) | 0.1030 (7) | |
| H7A | 0.9884 | 0.8938 | 0.0878 | 0.155* | |
| H7B | 0.8486 | 0.9288 | 0.1759 | 0.155* | |
| H7C | 0.7964 | 0.9893 | 0.0559 | 0.155* | |
| C8 | 0.63944 (15) | 0.47439 (11) | 0.10306 (9) | 0.0429 (3) | |
| C9 | 0.53578 (15) | 0.42485 (10) | 0.19465 (9) | 0.0401 (3) | |
| C10 | 0.51789 (15) | 0.46279 (11) | 0.28466 (9) | 0.0424 (3) | |
| H10 | 0.5567 | 0.5329 | 0.2825 | 0.051* | |
| C11 | 0.55904 (19) | 0.21206 (12) | 0.15682 (10) | 0.0547 (3) | |
| H11 | 0.6800 | 0.1879 | 0.1413 | 0.066* | |
| C12 | 0.29544 (19) | 0.21363 (13) | 0.18201 (9) | 0.0522 (3) | |
| C13 | 0.29627 (17) | 0.32641 (12) | 0.20011 (9) | 0.0479 (3) | |
| H13 | 0.2010 | 0.3902 | 0.2198 | 0.057* | |
| C14 | 0.44576 (16) | 0.41062 (12) | 0.38765 (9) | 0.0442 (3) | |
| C15 | 0.31154 (16) | 0.49758 (13) | 0.43426 (9) | 0.0497 (3) | |
| C16 | 0.23060 (19) | 0.62857 (14) | 0.38169 (12) | 0.0604 (4) | |
| H16 | 0.2649 | 0.6593 | 0.3130 | 0.072* | |
| C17 | 0.1035 (2) | 0.71059 (18) | 0.42967 (15) | 0.0772 (5) | |
| H17 | 0.0528 | 0.7965 | 0.3936 | 0.093* | |
| C18 | 0.0482 (2) | 0.6666 (2) | 0.53315 (16) | 0.0844 (6) | |
| H18 | −0.0377 | 0.7238 | 0.5655 | 0.101* | |
| C19 | 0.1187 (2) | 0.5429 (2) | 0.58552 (13) | 0.0770 (5) | |
| H19 | 0.0799 | 0.5152 | 0.6538 | 0.092* | |
| C20 | 0.25212 (18) | 0.45250 (17) | 0.53893 (10) | 0.0587 (4) | |
| C21 | 0.3253 (2) | 0.32471 (18) | 0.59118 (10) | 0.0668 (4) | |
| H21 | 0.2843 | 0.2958 | 0.6585 | 0.080* | |
| C22 | 0.4581 (2) | 0.23721 (15) | 0.54715 (10) | 0.0609 (4) | |
| C23 | 0.5358 (3) | 0.10705 (19) | 0.60296 (13) | 0.0849 (5) | |
| H23 | 0.4934 | 0.0776 | 0.6698 | 0.102* | |
| C24 | 0.6697 (3) | 0.02531 (18) | 0.56107 (15) | 0.0961 (6) | |
| H24 | 0.7168 | −0.0604 | 0.5983 | 0.115* | |
| C25 | 0.7395 (3) | 0.06850 (16) | 0.46106 (13) | 0.0800 (5) | |
| H25 | 0.8346 | 0.0116 | 0.4339 | 0.096* | |
| C26 | 0.6691 (2) | 0.19203 (13) | 0.40416 (11) | 0.0588 (4) | |
| H26 | 0.7175 | 0.2190 | 0.3386 | 0.071* | |
| C27 | 0.52314 (18) | 0.28088 (13) | 0.44281 (9) | 0.0495 (3) | |
| N1 | 0.46726 (13) | 0.32578 (9) | 0.18306 (7) | 0.0428 (2) | |
| N2 | 0.45809 (17) | 0.14128 (11) | 0.15594 (9) | 0.0602 (3) | |
| N4 | 0.1423 (2) | 0.17060 (15) | 0.18753 (10) | 0.0718 (4) | |
| O1 | 0.69016 (12) | 0.41643 (9) | 0.03388 (7) | 0.0576 (3) | |
| O2 | 0.1606 (2) | 0.06711 (14) | 0.16772 (11) | 0.1051 (5) | |
| O3 | 0.00028 (18) | 0.24220 (15) | 0.21342 (12) | 0.0975 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0851 (10) | 0.0617 (9) | 0.0534 (8) | −0.0413 (8) | 0.0181 (7) | −0.0175 (7) |
| C2 | 0.0631 (9) | 0.0805 (10) | 0.0669 (9) | −0.0393 (8) | 0.0181 (7) | −0.0256 (8) |
| C3 | 0.0561 (8) | 0.0585 (8) | 0.0523 (7) | −0.0224 (6) | 0.0110 (6) | −0.0185 (6) |
| C4 | 0.0526 (7) | 0.0487 (7) | 0.0330 (6) | −0.0207 (5) | 0.0039 (5) | −0.0070 (5) |
| C5 | 0.0549 (7) | 0.0518 (7) | 0.0487 (7) | −0.0175 (6) | 0.0043 (6) | −0.0088 (6) |
| C6 | 0.0793 (10) | 0.0476 (7) | 0.0520 (8) | −0.0192 (7) | 0.0090 (7) | −0.0113 (6) |
| C7 | 0.1274 (17) | 0.0883 (13) | 0.1247 (16) | −0.0694 (13) | 0.0351 (14) | −0.0441 (12) |
| C8 | 0.0430 (6) | 0.0459 (6) | 0.0378 (6) | −0.0122 (5) | −0.0015 (5) | −0.0083 (5) |
| C9 | 0.0436 (6) | 0.0390 (6) | 0.0385 (6) | −0.0150 (5) | −0.0023 (5) | −0.0078 (5) |
| C10 | 0.0473 (6) | 0.0432 (6) | 0.0399 (6) | −0.0189 (5) | −0.0012 (5) | −0.0094 (5) |
| C11 | 0.0663 (8) | 0.0466 (7) | 0.0539 (7) | −0.0195 (6) | 0.0048 (6) | −0.0160 (6) |
| C12 | 0.0684 (9) | 0.0562 (8) | 0.0393 (6) | −0.0335 (7) | −0.0051 (6) | −0.0049 (5) |
| C13 | 0.0509 (7) | 0.0533 (7) | 0.0419 (6) | −0.0211 (6) | −0.0030 (5) | −0.0089 (5) |
| C14 | 0.0501 (7) | 0.0566 (7) | 0.0347 (6) | −0.0276 (6) | −0.0006 (5) | −0.0122 (5) |
| C15 | 0.0491 (7) | 0.0693 (9) | 0.0428 (6) | −0.0290 (6) | 0.0004 (5) | −0.0216 (6) |
| C16 | 0.0582 (8) | 0.0705 (9) | 0.0604 (8) | −0.0221 (7) | 0.0010 (6) | −0.0276 (7) |
| C17 | 0.0632 (9) | 0.0857 (11) | 0.0916 (12) | −0.0160 (8) | −0.0031 (8) | −0.0463 (10) |
| C18 | 0.0562 (9) | 0.1257 (17) | 0.0902 (13) | −0.0252 (10) | 0.0098 (9) | −0.0667 (13) |
| C19 | 0.0564 (9) | 0.1382 (17) | 0.0592 (9) | −0.0450 (10) | 0.0129 (7) | −0.0491 (11) |
| C20 | 0.0508 (7) | 0.0984 (11) | 0.0442 (7) | −0.0399 (7) | 0.0042 (6) | −0.0274 (7) |
| C21 | 0.0708 (9) | 0.1096 (13) | 0.0367 (7) | −0.0552 (9) | 0.0048 (6) | −0.0134 (8) |
| C22 | 0.0771 (10) | 0.0761 (9) | 0.0401 (7) | −0.0446 (8) | −0.0072 (6) | −0.0034 (6) |
| C23 | 0.1265 (16) | 0.0850 (12) | 0.0485 (8) | −0.0569 (12) | −0.0116 (9) | 0.0089 (8) |
| C24 | 0.151 (2) | 0.0634 (10) | 0.0639 (11) | −0.0333 (12) | −0.0260 (12) | 0.0091 (9) |
| C25 | 0.1040 (13) | 0.0594 (9) | 0.0676 (10) | −0.0148 (9) | −0.0201 (9) | −0.0081 (8) |
| C26 | 0.0715 (9) | 0.0565 (8) | 0.0480 (7) | −0.0221 (7) | −0.0097 (6) | −0.0065 (6) |
| C27 | 0.0603 (8) | 0.0576 (8) | 0.0378 (6) | −0.0308 (6) | −0.0062 (5) | −0.0065 (5) |
| N1 | 0.0501 (6) | 0.0427 (5) | 0.0385 (5) | −0.0179 (4) | −0.0008 (4) | −0.0105 (4) |
| N2 | 0.0837 (9) | 0.0513 (6) | 0.0546 (7) | −0.0321 (6) | 0.0017 (6) | −0.0150 (5) |
| N4 | 0.0921 (10) | 0.0831 (9) | 0.0569 (7) | −0.0572 (9) | −0.0091 (7) | −0.0046 (7) |
| O1 | 0.0656 (6) | 0.0654 (6) | 0.0495 (5) | −0.0253 (5) | 0.0130 (4) | −0.0253 (5) |
| O2 | 0.1427 (12) | 0.1039 (10) | 0.1091 (10) | −0.0885 (10) | −0.0031 (9) | −0.0309 (8) |
| O3 | 0.0747 (8) | 0.1167 (11) | 0.1149 (11) | −0.0555 (8) | 0.0020 (7) | −0.0195 (8) |
| C1—C2 | 1.378 (2) | C13—H13 | 0.93 |
| C1—C6 | 1.383 (2) | C14—C27 | 1.4085 (18) |
| C1—C7 | 1.509 (2) | C14—C15 | 1.4099 (17) |
| C2—C3 | 1.3779 (19) | C15—C16 | 1.414 (2) |
| C2—H2 | 0.93 | C15—C20 | 1.4327 (18) |
| C3—C4 | 1.3852 (18) | C16—C17 | 1.361 (2) |
| C3—H3 | 0.93 | C16—H16 | 0.93 |
| C4—C5 | 1.3835 (18) | C17—C18 | 1.405 (3) |
| C4—C8 | 1.4923 (16) | C17—H17 | 0.93 |
| C5—C6 | 1.3814 (18) | C18—C19 | 1.339 (3) |
| C5—H5 | 0.93 | C18—H18 | 0.93 |
| C6—H6 | 0.93 | C19—C20 | 1.429 (2) |
| C7—H7A | 0.96 | C19—H19 | 0.93 |
| C7—H7B | 0.96 | C20—C21 | 1.377 (2) |
| C7—H7C | 0.96 | C21—C22 | 1.390 (2) |
| C8—O1 | 1.2133 (13) | C21—H21 | 0.93 |
| C8—C9 | 1.4933 (16) | C22—C23 | 1.415 (2) |
| C9—C10 | 1.3289 (15) | C22—C27 | 1.4426 (18) |
| C9—N1 | 1.4332 (14) | C23—C24 | 1.344 (3) |
| C10—C14 | 1.4772 (15) | C23—H23 | 0.93 |
| C10—H10 | 0.93 | C24—C25 | 1.411 (3) |
| C11—N2 | 1.3029 (17) | C24—H24 | 0.93 |
| C11—N1 | 1.3657 (16) | C25—C26 | 1.355 (2) |
| C11—H11 | 0.93 | C25—H25 | 0.93 |
| C12—C13 | 1.3510 (17) | C26—C27 | 1.418 (2) |
| C12—N2 | 1.3551 (18) | C26—H26 | 0.93 |
| C12—N4 | 1.4381 (18) | N4—O2 | 1.2174 (17) |
| C13—N1 | 1.3563 (15) | N4—O3 | 1.2346 (18) |
| C2—C1—C6 | 118.62 (13) | C14—C15—C20 | 119.28 (13) |
| C2—C1—C7 | 120.37 (15) | C16—C15—C20 | 117.91 (12) |
| C6—C1—C7 | 121.01 (15) | C17—C16—C15 | 121.32 (15) |
| C1—C2—C3 | 120.94 (14) | C17—C16—H16 | 119.3 |
| C1—C2—H2 | 119.5 | C15—C16—H16 | 119.3 |
| C3—C2—H2 | 119.5 | C16—C17—C18 | 120.57 (18) |
| C2—C3—C4 | 120.40 (13) | C16—C17—H17 | 119.7 |
| C2—C3—H3 | 119.8 | C18—C17—H17 | 119.7 |
| C4—C3—H3 | 119.8 | C19—C18—C17 | 120.34 (16) |
| C5—C4—C3 | 118.92 (12) | C19—C18—H18 | 119.8 |
| C5—C4—C8 | 123.45 (11) | C17—C18—H18 | 119.8 |
| C3—C4—C8 | 117.62 (11) | C18—C19—C20 | 121.48 (16) |
| C6—C5—C4 | 120.24 (13) | C18—C19—H19 | 119.3 |
| C6—C5—H5 | 119.9 | C20—C19—H19 | 119.3 |
| C4—C5—H5 | 119.9 | C21—C20—C19 | 122.36 (14) |
| C5—C6—C1 | 120.85 (13) | C21—C20—C15 | 119.29 (13) |
| C5—C6—H6 | 119.6 | C19—C20—C15 | 118.35 (15) |
| C1—C6—H6 | 119.6 | C20—C21—C22 | 122.53 (12) |
| C1—C7—H7A | 109.5 | C20—C21—H21 | 118.7 |
| C1—C7—H7B | 109.5 | C22—C21—H21 | 118.7 |
| H7A—C7—H7B | 109.5 | C21—C22—C23 | 121.93 (14) |
| C1—C7—H7C | 109.5 | C21—C22—C27 | 119.26 (13) |
| H7A—C7—H7C | 109.5 | C23—C22—C27 | 118.78 (16) |
| H7B—C7—H7C | 109.5 | C24—C23—C22 | 121.12 (16) |
| O1—C8—C4 | 121.31 (10) | C24—C23—H23 | 119.4 |
| O1—C8—C9 | 120.52 (11) | C22—C23—H23 | 119.4 |
| C4—C8—C9 | 118.02 (10) | C23—C24—C25 | 120.55 (16) |
| C10—C9—N1 | 121.36 (10) | C23—C24—H24 | 119.7 |
| C10—C9—C8 | 122.61 (10) | C25—C24—H24 | 119.7 |
| N1—C9—C8 | 115.87 (9) | C26—C25—C24 | 120.61 (18) |
| C9—C10—C14 | 129.89 (10) | C26—C25—H25 | 119.7 |
| C9—C10—H10 | 115.1 | C24—C25—H25 | 119.7 |
| C14—C10—H10 | 115.1 | C25—C26—C27 | 121.12 (14) |
| N2—C11—N1 | 112.40 (13) | C25—C26—H26 | 119.4 |
| N2—C11—H11 | 123.8 | C27—C26—H26 | 119.4 |
| N1—C11—H11 | 123.8 | C14—C27—C26 | 123.60 (11) |
| C13—C12—N2 | 112.85 (11) | C14—C27—C22 | 118.59 (13) |
| C13—C12—N4 | 125.76 (14) | C26—C27—C22 | 117.70 (12) |
| N2—C12—N4 | 121.39 (13) | C13—N1—C11 | 106.73 (10) |
| C12—C13—N1 | 104.50 (11) | C13—N1—C9 | 125.53 (10) |
| C12—C13—H13 | 127.7 | C11—N1—C9 | 127.71 (11) |
| N1—C13—H13 | 127.7 | C11—N2—C12 | 103.51 (11) |
| C27—C14—C15 | 121.01 (11) | O2—N4—O3 | 124.53 (15) |
| C27—C14—C10 | 120.56 (11) | O2—N4—C12 | 118.72 (16) |
| C15—C14—C10 | 118.04 (11) | O3—N4—C12 | 116.74 (13) |
| C14—C15—C16 | 122.80 (11) | ||
| C6—C1—C2—C3 | −0.8 (2) | C14—C15—C20—C19 | 178.69 (11) |
| C7—C1—C2—C3 | 179.16 (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—C5 | 1.47 (19) | C15—C20—C21—C22 | 1.3 (2) |
| C2—C3—C4—C8 | −179.46 (11) | C20—C21—C22—C23 | 178.14 (14) |
| C3—C4—C5—C6 | −0.28 (18) | C20—C21—C22—C27 | 0.1 (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—C24 | 1.1 (3) |
| C2—C1—C6—C5 | 2.0 (2) | C22—C23—C24—C25 | 1.6 (3) |
| C7—C1—C6—C5 | −177.96 (14) | C23—C24—C25—C26 | −2.0 (3) |
| C5—C4—C8—O1 | 127.74 (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—C9 | 124.27 (12) | C15—C14—C27—C22 | 2.01 (17) |
| O1—C8—C9—C10 | 161.69 (12) | C10—C14—C27—C22 | 174.76 (11) |
| C4—C8—C9—C10 | −13.90 (17) | C25—C26—C27—C14 | 179.39 (13) |
| O1—C8—C9—N1 | −13.70 (16) | C25—C26—C27—C22 | 3.2 (2) |
| C4—C8—C9—N1 | 170.72 (10) | C21—C22—C27—C14 | −1.75 (18) |
| N1—C9—C10—C14 | 5.68 (19) | C23—C22—C27—C14 | −179.84 (13) |
| C8—C9—C10—C14 | −169.46 (11) | C21—C22—C27—C26 | 174.64 (12) |
| N2—C12—C13—N1 | 0.92 (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—C27 | 59.15 (18) | C12—C13—N1—C9 | −178.63 (10) |
| C9—C10—C14—C15 | −127.88 (14) | N2—C11—N1—C13 | 0.13 (14) |
| C27—C14—C15—C16 | 179.91 (11) | N2—C11—N1—C9 | 178.09 (10) |
| C10—C14—C15—C16 | 6.98 (17) | C10—C9—N1—C13 | 54.97 (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—C11 | 52.83 (15) |
| C20—C15—C16—C17 | 1.70 (19) | N1—C11—N2—C12 | 0.41 (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—C11 | 178.56 (11) |
| C17—C18—C19—C20 | 0.5 (2) | C13—C12—N4—O2 | 178.97 (13) |
| C18—C19—C20—C21 | −179.54 (14) | N2—C12—N4—O2 | −0.34 (19) |
| C18—C19—C20—C15 | 0.8 (2) | C13—C12—N4—O3 | −1.7 (2) |
| C14—C15—C20—C21 | −1.03 (17) | N2—C12—N4—O3 | 178.98 (13) |
| C16—C15—C20—C21 | 178.45 (12) |
The authors thank Southwest University (grant Nos. SWUB2006018, XSGX0602 and SWUF2007023) and the Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.
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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).