Acta Cryst. (2009). E65, o792 [ doi:10.1107/S1600536809008447 ]
In the title compound, C27H16Cl2N4, the benzimidazo[1,2-a]benzo[f][1,8]naphthyridine system is nearly planar (r.m.s. deviation for all non-H atoms = 0.033 Å). The dichlorophenyl substituent is rotated by -67.5 (2)° from this plane. In the crystal structure, molecules form stacks along the crystallographic (100) direction due to ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking interactions with a centroid-centroid distance of 3.4283 (9) Å.
The title compound was synthesized by the reaction of 3-chloro-1-(2,3-dichlorophenyl)isoquinoline-4-carbaldehyde (1 mmol) with (5,6-dimethyl-1H-benzimidazol-2-yl)acetonitrile (1 mmol) in dimethylformamide (3–4 ml). After refluxing for 3 h, the reaction mixture was left to stand for overnight. The resulting crude solid was filtered, washed twice with acetone (10 ml) and dried. Yield: 65%. Crystals suitable for X-ray analysis were obtained by slow crystallization from hot dimethylformamide.
H-atoms were placed in calculated positions with d(C—H)=0.93–0.96 Å and refined using riding model with Uiso(H) = nUeq(C) (n = 1.2 for aromatic C—H and n = 1.5 for methyl groups).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2009).
![[Figure 1]](./sj2589fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. |
![[Figure 2]](./sj2589fig2thm.gif)
| Fig. 2. Crystal packing of the title compound showing stacks along the a axis. Hydrogen atoms are not shown. |
| C27H16Cl2N4 | Z = 2 |
| Mr = 467.34 | F(000) = 480 |
| Triclinic, P1 | Dx = 1.416 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
| a = 8.5588 (8) Å | Cell parameters from 6294 reflections |
| b = 11.0751 (13) Å | θ = 2.7–28.6° |
| c = 12.2332 (11) Å | µ = 0.32 mm−1 |
| α = 76.985 (9)° | T = 293 K |
| β = 75.986 (8)° | Prism, pale orange |
| γ = 85.438 (9)° | 0.6 × 0.1 × 0.1 mm |
| V = 1095.77 (19) Å3 |
| Oxford-Diffraction Xcalibur-3 diffractometer | 4290 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 2405 reflections with I > 2σ(I) |
| graphite | Rint = 0.034 |
| Detector resolution: 16.1827 pixels mm-1 | θmax = 26.0°, θmin = 2.7° |
| ω scans | h = −10→10 |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −13→13 |
| Tmin = 0.82, Tmax = 0.97 | l = −15→15 |
| 20237 measured reflections |
| 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.072 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
| 4290 reflections | (Δ/σ)max < 0.001 |
| 300 parameters | Δρmax = 0.19 e Å−3 |
| 0 restraints | Δρmin = −0.24 e Å−3 |
| C27H16Cl2N4 | γ = 85.438 (9)° |
| Mr = 467.34 | V = 1095.77 (19) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.5588 (8) Å | Mo Kα radiation |
| b = 11.0751 (13) Å | µ = 0.32 mm−1 |
| c = 12.2332 (11) Å | T = 293 K |
| α = 76.985 (9)° | 0.6 × 0.1 × 0.1 mm |
| β = 75.986 (8)° |
| Oxford-Diffraction Xcalibur-3 diffractometer | 4290 independent reflections |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2405 reflections with I > 2σ(I) |
| Tmin = 0.82, Tmax = 0.97 | Rint = 0.034 |
| 20237 measured reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
| wR(F2) = 0.072 | Δρmax = 0.19 e Å−3 |
| S = 1.01 | Δρmin = −0.24 e Å−3 |
| 4290 reflections | Absolute structure: ? |
| 300 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 | ||
| Cl1 | 0.53369 (8) | 0.08996 (5) | 0.11087 (4) | 0.07512 (19) | |
| Cl2 | 0.55737 (9) | 0.26410 (6) | −0.13175 (4) | 0.0980 (2) | |
| N1 | 0.24410 (16) | 0.07841 (12) | 0.33502 (10) | 0.0416 (4) | |
| N2 | 0.15186 (16) | −0.10485 (12) | 0.46081 (10) | 0.0380 (3) | |
| N3 | 0.05348 (17) | −0.29056 (13) | 0.56580 (11) | 0.0445 (4) | |
| N4 | 0.1445 (2) | −0.31290 (16) | 0.85388 (14) | 0.0799 (6) | |
| C1 | 0.4249 (2) | 0.22794 (16) | 0.09828 (14) | 0.0478 (5) | |
| C2 | 0.4347 (2) | 0.30496 (19) | −0.01113 (14) | 0.0553 (5) | |
| C3 | 0.3485 (2) | 0.41496 (19) | −0.02191 (16) | 0.0599 (6) | |
| H3A | 0.3550 | 0.4660 | −0.0944 | 0.072* | |
| C4 | 0.2526 (2) | 0.45022 (18) | 0.07372 (17) | 0.0637 (6) | |
| H4A | 0.1933 | 0.5244 | 0.0653 | 0.076* | |
| C5 | 0.2435 (2) | 0.37670 (17) | 0.18209 (15) | 0.0575 (5) | |
| H5A | 0.1802 | 0.4023 | 0.2465 | 0.069* | |
| C6 | 0.3291 (2) | 0.26398 (16) | 0.19503 (13) | 0.0439 (4) | |
| C7 | 0.3168 (2) | 0.18469 (15) | 0.31350 (13) | 0.0411 (4) | |
| C8 | 0.22786 (19) | 0.00654 (15) | 0.44182 (13) | 0.0373 (4) | |
| C9 | 0.1249 (2) | −0.19032 (15) | 0.56664 (13) | 0.0388 (4) | |
| C10 | 0.0316 (2) | −0.27288 (15) | 0.45439 (13) | 0.0402 (4) | |
| C11 | 0.0918 (2) | −0.15919 (15) | 0.38690 (13) | 0.0388 (4) | |
| C12 | 0.0814 (2) | −0.12061 (16) | 0.27243 (14) | 0.0469 (5) | |
| H12A | 0.1221 | −0.0450 | 0.2283 | 0.056* | |
| C13 | 0.0089 (2) | −0.19800 (17) | 0.22635 (14) | 0.0506 (5) | |
| C14 | −0.0526 (2) | −0.31292 (16) | 0.29292 (15) | 0.0471 (5) | |
| C15 | −0.0407 (2) | −0.34975 (16) | 0.40614 (14) | 0.0457 (4) | |
| H15A | −0.0808 | −0.4256 | 0.4501 | 0.055* | |
| C16 | −0.1334 (2) | −0.39560 (17) | 0.24225 (15) | 0.0624 (6) | |
| H16A | −0.1458 | −0.4763 | 0.2922 | 0.094* | |
| H16B | −0.0686 | −0.4025 | 0.1679 | 0.094* | |
| H16C | −0.2374 | −0.3607 | 0.2343 | 0.094* | |
| C17 | −0.0053 (3) | −0.1566 (2) | 0.10197 (16) | 0.0844 (7) | |
| H17A | 0.0436 | −0.0775 | 0.0691 | 0.127* | |
| H17B | −0.1170 | −0.1497 | 0.0995 | 0.127* | |
| H17C | 0.0485 | −0.2164 | 0.0588 | 0.127* | |
| C18 | 0.1780 (2) | −0.15844 (16) | 0.65802 (13) | 0.0421 (4) | |
| C19 | 0.1568 (2) | −0.24516 (17) | 0.76740 (15) | 0.0527 (5) | |
| C20 | 0.2535 (2) | −0.05020 (16) | 0.64046 (13) | 0.0431 (4) | |
| H20A | 0.2882 | −0.0312 | 0.7009 | 0.052* | |
| C21 | 0.28103 (19) | 0.03485 (15) | 0.53223 (13) | 0.0375 (4) | |
| C22 | 0.36455 (19) | 0.14875 (15) | 0.50764 (13) | 0.0392 (4) | |
| C23 | 0.3824 (2) | 0.22500 (15) | 0.39544 (13) | 0.0396 (4) | |
| C24 | 0.4691 (2) | 0.33565 (16) | 0.36838 (15) | 0.0491 (5) | |
| H24A | 0.4811 | 0.3866 | 0.2954 | 0.059* | |
| C25 | 0.5350 (2) | 0.36845 (17) | 0.44770 (15) | 0.0534 (5) | |
| H25A | 0.5927 | 0.4409 | 0.4284 | 0.064* | |
| C26 | 0.5162 (2) | 0.29336 (17) | 0.55808 (16) | 0.0530 (5) | |
| H26A | 0.5612 | 0.3166 | 0.6120 | 0.064* | |
| C27 | 0.4328 (2) | 0.18652 (16) | 0.58793 (14) | 0.0462 (5) | |
| H27A | 0.4208 | 0.1381 | 0.6620 | 0.055* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.1038 (5) | 0.0659 (4) | 0.0530 (3) | 0.0237 (3) | −0.0178 (3) | −0.0166 (3) |
| Cl2 | 0.1300 (6) | 0.1142 (5) | 0.0412 (3) | 0.0138 (5) | −0.0102 (3) | −0.0149 (3) |
| N1 | 0.0466 (9) | 0.0348 (8) | 0.0384 (8) | −0.0005 (7) | −0.0089 (7) | 0.0011 (7) |
| N2 | 0.0416 (9) | 0.0340 (8) | 0.0337 (8) | 0.0004 (7) | −0.0077 (6) | 0.0009 (6) |
| N3 | 0.0464 (9) | 0.0416 (9) | 0.0402 (9) | −0.0028 (8) | −0.0085 (7) | 0.0013 (7) |
| N4 | 0.1199 (17) | 0.0661 (12) | 0.0471 (10) | −0.0184 (12) | −0.0227 (10) | 0.0103 (9) |
| C1 | 0.0549 (13) | 0.0468 (11) | 0.0441 (11) | −0.0044 (10) | −0.0180 (9) | −0.0066 (9) |
| C2 | 0.0628 (14) | 0.0632 (13) | 0.0401 (11) | −0.0086 (11) | −0.0163 (10) | −0.0043 (10) |
| C3 | 0.0633 (15) | 0.0666 (15) | 0.0446 (12) | −0.0157 (12) | −0.0172 (11) | 0.0085 (10) |
| C4 | 0.0627 (15) | 0.0506 (12) | 0.0649 (14) | 0.0010 (11) | −0.0148 (11) | 0.0131 (10) |
| C5 | 0.0586 (14) | 0.0491 (12) | 0.0512 (12) | 0.0007 (10) | −0.0083 (10) | 0.0114 (10) |
| C6 | 0.0466 (12) | 0.0427 (11) | 0.0392 (10) | −0.0091 (9) | −0.0111 (9) | 0.0019 (8) |
| C7 | 0.0421 (11) | 0.0370 (10) | 0.0383 (10) | 0.0007 (9) | −0.0047 (8) | −0.0015 (8) |
| C8 | 0.0360 (10) | 0.0325 (10) | 0.0373 (10) | 0.0022 (8) | −0.0036 (8) | −0.0011 (8) |
| C9 | 0.0392 (11) | 0.0362 (10) | 0.0341 (10) | 0.0024 (9) | −0.0040 (8) | 0.0012 (8) |
| C10 | 0.0399 (11) | 0.0368 (10) | 0.0381 (10) | 0.0028 (9) | −0.0071 (8) | 0.0004 (8) |
| C11 | 0.0380 (11) | 0.0387 (10) | 0.0375 (10) | 0.0033 (8) | −0.0085 (8) | −0.0054 (8) |
| C12 | 0.0576 (13) | 0.0360 (10) | 0.0430 (11) | −0.0020 (9) | −0.0112 (9) | −0.0003 (9) |
| C13 | 0.0597 (13) | 0.0474 (12) | 0.0431 (11) | 0.0017 (10) | −0.0130 (10) | −0.0062 (9) |
| C14 | 0.0433 (11) | 0.0476 (11) | 0.0505 (11) | 0.0035 (9) | −0.0107 (9) | −0.0125 (9) |
| C15 | 0.0464 (12) | 0.0358 (10) | 0.0512 (11) | −0.0033 (9) | −0.0095 (9) | −0.0027 (9) |
| C16 | 0.0685 (15) | 0.0579 (13) | 0.0648 (13) | −0.0059 (11) | −0.0189 (11) | −0.0160 (10) |
| C17 | 0.133 (2) | 0.0714 (15) | 0.0532 (13) | −0.0218 (15) | −0.0388 (14) | 0.0033 (11) |
| C18 | 0.0460 (12) | 0.0394 (11) | 0.0356 (10) | 0.0031 (9) | −0.0074 (8) | −0.0010 (8) |
| C19 | 0.0657 (14) | 0.0483 (12) | 0.0418 (11) | −0.0077 (10) | −0.0122 (10) | −0.0025 (10) |
| C20 | 0.0480 (12) | 0.0437 (11) | 0.0365 (10) | 0.0034 (9) | −0.0109 (8) | −0.0064 (8) |
| C21 | 0.0366 (11) | 0.0365 (10) | 0.0357 (9) | 0.0051 (8) | −0.0062 (8) | −0.0041 (8) |
| C22 | 0.0352 (11) | 0.0384 (10) | 0.0408 (10) | 0.0061 (9) | −0.0049 (8) | −0.0083 (8) |
| C23 | 0.0396 (11) | 0.0338 (10) | 0.0401 (10) | 0.0024 (8) | −0.0035 (8) | −0.0043 (8) |
| C24 | 0.0539 (13) | 0.0398 (11) | 0.0470 (11) | −0.0029 (10) | −0.0032 (9) | −0.0041 (9) |
| C25 | 0.0542 (13) | 0.0448 (11) | 0.0598 (13) | −0.0071 (10) | −0.0039 (10) | −0.0161 (10) |
| C26 | 0.0537 (13) | 0.0525 (12) | 0.0561 (12) | 0.0000 (10) | −0.0118 (10) | −0.0195 (10) |
| C27 | 0.0501 (12) | 0.0441 (11) | 0.0436 (10) | 0.0043 (10) | −0.0108 (9) | −0.0094 (9) |
| Cl1—C1 | 1.7214 (18) | C12—H12A | 0.9300 |
| Cl2—C2 | 1.7201 (19) | C13—C14 | 1.411 (2) |
| N1—C7 | 1.319 (2) | C13—C17 | 1.519 (2) |
| N1—C8 | 1.3495 (19) | C14—C15 | 1.379 (2) |
| N2—C8 | 1.3873 (19) | C14—C16 | 1.505 (2) |
| N2—C11 | 1.4009 (19) | C15—H15A | 0.9300 |
| N2—C9 | 1.4013 (19) | C16—H16A | 0.9600 |
| N3—C9 | 1.3123 (19) | C16—H16B | 0.9600 |
| N3—C10 | 1.3886 (19) | C16—H16C | 0.9600 |
| N4—C19 | 1.138 (2) | C17—H17A | 0.9600 |
| C1—C6 | 1.387 (2) | C17—H17B | 0.9600 |
| C1—C2 | 1.403 (2) | C17—H17C | 0.9600 |
| C2—C3 | 1.370 (3) | C18—C20 | 1.357 (2) |
| C3—C4 | 1.373 (2) | C18—C19 | 1.441 (2) |
| C3—H3A | 0.9300 | C20—C21 | 1.421 (2) |
| C4—C5 | 1.378 (2) | C20—H20A | 0.9300 |
| C4—H4A | 0.9300 | C21—C22 | 1.436 (2) |
| C5—C6 | 1.393 (2) | C22—C27 | 1.408 (2) |
| C5—H5A | 0.9300 | C22—C23 | 1.420 (2) |
| C6—C7 | 1.500 (2) | C23—C24 | 1.416 (2) |
| C7—C23 | 1.426 (2) | C24—C25 | 1.360 (2) |
| C8—C21 | 1.397 (2) | C24—H24A | 0.9300 |
| C9—C18 | 1.425 (2) | C25—C26 | 1.397 (2) |
| C10—C15 | 1.394 (2) | C25—H25A | 0.9300 |
| C10—C11 | 1.401 (2) | C26—C27 | 1.363 (2) |
| C11—C12 | 1.392 (2) | C26—H26A | 0.9300 |
| C12—C13 | 1.382 (2) | C27—H27A | 0.9300 |
| C7—N1—C8 | 117.45 (14) | C15—C14—C16 | 119.31 (16) |
| C8—N2—C11 | 131.25 (13) | C13—C14—C16 | 120.72 (16) |
| C8—N2—C9 | 123.19 (13) | C14—C15—C10 | 119.72 (16) |
| C11—N2—C9 | 105.54 (13) | C14—C15—H15A | 120.1 |
| C9—N3—C10 | 104.64 (13) | C10—C15—H15A | 120.1 |
| C6—C1—C2 | 119.87 (16) | C14—C16—H16A | 109.5 |
| C6—C1—Cl1 | 120.71 (13) | C14—C16—H16B | 109.5 |
| C2—C1—Cl1 | 119.42 (14) | H16A—C16—H16B | 109.5 |
| C3—C2—C1 | 119.80 (17) | C14—C16—H16C | 109.5 |
| C3—C2—Cl2 | 119.59 (15) | H16A—C16—H16C | 109.5 |
| C1—C2—Cl2 | 120.60 (15) | H16B—C16—H16C | 109.5 |
| C2—C3—C4 | 120.37 (17) | C13—C17—H17A | 109.5 |
| C2—C3—H3A | 119.8 | C13—C17—H17B | 109.5 |
| C4—C3—H3A | 119.8 | H17A—C17—H17B | 109.5 |
| C3—C4—C5 | 120.64 (18) | C13—C17—H17C | 109.5 |
| C3—C4—H4A | 119.7 | H17A—C17—H17C | 109.5 |
| C5—C4—H4A | 119.7 | H17B—C17—H17C | 109.5 |
| C4—C5—C6 | 119.98 (18) | C20—C18—C9 | 120.27 (14) |
| C4—C5—H5A | 120.0 | C20—C18—C19 | 120.64 (15) |
| C6—C5—H5A | 120.0 | C9—C18—C19 | 119.04 (15) |
| C1—C6—C5 | 119.33 (15) | N4—C19—C18 | 178.0 (2) |
| C1—C6—C7 | 121.37 (15) | C18—C20—C21 | 121.74 (15) |
| C5—C6—C7 | 119.29 (15) | C18—C20—H20A | 119.1 |
| N1—C7—C23 | 123.58 (14) | C21—C20—H20A | 119.1 |
| N1—C7—C6 | 116.15 (14) | C8—C21—C20 | 119.06 (15) |
| C23—C7—C6 | 120.27 (15) | C8—C21—C22 | 116.76 (14) |
| N1—C8—N2 | 115.72 (14) | C20—C21—C22 | 124.16 (14) |
| N1—C8—C21 | 125.72 (15) | C27—C22—C23 | 118.74 (16) |
| N2—C8—C21 | 118.56 (13) | C27—C22—C21 | 123.32 (15) |
| N3—C9—N2 | 113.47 (14) | C23—C22—C21 | 117.92 (14) |
| N3—C9—C18 | 129.35 (14) | C24—C23—C22 | 118.74 (15) |
| N2—C9—C18 | 117.18 (15) | C24—C23—C7 | 122.71 (15) |
| N3—C10—C15 | 129.18 (15) | C22—C23—C7 | 118.51 (16) |
| N3—C10—C11 | 111.38 (15) | C25—C24—C23 | 120.91 (16) |
| C15—C10—C11 | 119.44 (15) | C25—C24—H24A | 119.5 |
| C12—C11—C10 | 121.67 (16) | C23—C24—H24A | 119.5 |
| C12—C11—N2 | 133.34 (16) | C24—C25—C26 | 120.03 (17) |
| C10—C11—N2 | 104.97 (13) | C24—C25—H25A | 120.0 |
| C13—C12—C11 | 117.98 (16) | C26—C25—H25A | 120.0 |
| C13—C12—H12A | 121.0 | C27—C26—C25 | 120.95 (17) |
| C11—C12—H12A | 121.0 | C27—C26—H26A | 119.5 |
| C12—C13—C14 | 121.22 (15) | C25—C26—H26A | 119.5 |
| C12—C13—C17 | 118.67 (17) | C26—C27—C22 | 120.63 (16) |
| C14—C13—C17 | 120.11 (17) | C26—C27—H27A | 119.7 |
| C15—C14—C13 | 119.97 (17) | C22—C27—H27A | 119.7 |
| C6—C1—C2—C3 | −0.6 (3) | N2—C11—C12—C13 | −178.08 (17) |
| Cl1—C1—C2—C3 | 180.00 (14) | C11—C12—C13—C14 | −0.2 (3) |
| C6—C1—C2—Cl2 | 178.11 (14) | C11—C12—C13—C17 | 179.24 (17) |
| Cl1—C1—C2—Cl2 | −1.3 (2) | C12—C13—C14—C15 | 0.0 (3) |
| C1—C2—C3—C4 | 0.1 (3) | C17—C13—C14—C15 | −179.43 (18) |
| Cl2—C2—C3—C4 | −178.65 (15) | C12—C13—C14—C16 | 179.13 (16) |
| C2—C3—C4—C5 | 1.0 (3) | C17—C13—C14—C16 | −0.3 (3) |
| C3—C4—C5—C6 | −1.5 (3) | C13—C14—C15—C10 | 0.2 (3) |
| C2—C1—C6—C5 | 0.1 (3) | C16—C14—C15—C10 | −178.96 (15) |
| Cl1—C1—C6—C5 | 179.47 (14) | N3—C10—C15—C14 | 178.80 (16) |
| C2—C1—C6—C7 | −179.36 (16) | C11—C10—C15—C14 | −0.2 (2) |
| Cl1—C1—C6—C7 | 0.0 (2) | N3—C9—C18—C20 | 178.47 (16) |
| C4—C5—C6—C1 | 1.0 (3) | N2—C9—C18—C20 | −1.0 (2) |
| C4—C5—C6—C7 | −179.58 (17) | N3—C9—C18—C19 | 1.2 (3) |
| C8—N1—C7—C23 | 1.9 (2) | N2—C9—C18—C19 | −178.29 (15) |
| C8—N1—C7—C6 | −178.42 (14) | C9—C18—C20—C21 | 0.5 (2) |
| C1—C6—C7—N1 | −67.7 (2) | C19—C18—C20—C21 | 177.75 (15) |
| C5—C6—C7—N1 | 112.84 (18) | N1—C8—C21—C20 | 179.41 (15) |
| C1—C6—C7—C23 | 111.97 (19) | N2—C8—C21—C20 | −0.9 (2) |
| C5—C6—C7—C23 | −67.5 (2) | N1—C8—C21—C22 | −2.0 (2) |
| C7—N1—C8—N2 | −179.53 (14) | N2—C8—C21—C22 | 177.66 (13) |
| C7—N1—C8—C21 | 0.2 (2) | C18—C20—C21—C8 | 0.4 (2) |
| C11—N2—C8—N1 | 2.2 (2) | C18—C20—C21—C22 | −177.98 (15) |
| C9—N2—C8—N1 | −179.90 (14) | C8—C21—C22—C27 | −176.46 (15) |
| C11—N2—C8—C21 | −177.54 (15) | C20—C21—C22—C27 | 2.0 (2) |
| C9—N2—C8—C21 | 0.4 (2) | C8—C21—C22—C23 | 1.8 (2) |
| C10—N3—C9—N2 | 0.31 (18) | C20—C21—C22—C23 | −179.73 (15) |
| C10—N3—C9—C18 | −179.18 (16) | C27—C22—C23—C24 | 0.4 (2) |
| C8—N2—C9—N3 | −178.98 (14) | C21—C22—C23—C24 | −177.92 (14) |
| C11—N2—C9—N3 | −0.62 (18) | C27—C22—C23—C7 | 178.34 (15) |
| C8—N2—C9—C18 | 0.6 (2) | C21—C22—C23—C7 | 0.0 (2) |
| C11—N2—C9—C18 | 178.94 (14) | N1—C7—C23—C24 | 175.85 (15) |
| C9—N3—C10—C15 | −178.96 (17) | C6—C7—C23—C24 | −3.8 (2) |
| C9—N3—C10—C11 | 0.12 (18) | N1—C7—C23—C22 | −2.0 (2) |
| N3—C10—C11—C12 | −179.17 (15) | C6—C7—C23—C22 | 178.35 (15) |
| C15—C10—C11—C12 | 0.0 (2) | C22—C23—C24—C25 | 0.4 (2) |
| N3—C10—C11—N2 | −0.49 (17) | C7—C23—C24—C25 | −177.44 (16) |
| C15—C10—C11—N2 | 178.69 (14) | C23—C24—C25—C26 | −0.7 (3) |
| C8—N2—C11—C12 | −2.7 (3) | C24—C25—C26—C27 | 0.3 (3) |
| C9—N2—C11—C12 | 179.09 (18) | C25—C26—C27—C22 | 0.5 (3) |
| C8—N2—C11—C10 | 178.81 (15) | C23—C22—C27—C26 | −0.9 (2) |
| C9—N2—C11—C10 | 0.63 (16) | C21—C22—C27—C26 | 177.38 (15) |
| C10—C11—C12—C13 | 0.2 (2) |
Bijan, P. D. & Basu, U. P. (1965). Indian J. Chem. 3, 268–272.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gokhale, U. V. & Seshadri, S. (1987). Dyes Pigm. 8, 157–163.
Kametami, T. & Fukomoto, K. (1981). The Chemistry of Heterocyclic Compounds: Isoquinolines, Part 1, edited by G. Grethe, p. 139. New York: John Wiley.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.
Neumeyer, J. L. & Weinhard, K. K. (1970). J. Med. Chem. 13, 613-618.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Rajagopal, R. & Seshadri, S. (1991). Dyes Pigm. 17, 57–69.
Shamma, M. (1972). The Isoquinoline Alkaloids. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Volovnenko, T. A., Tarasov, A. V. & Volovenko, Yu. M. (2006). Ukr. Khim. Zh. (Russ. Ed.), 72, 108–111.
Westrip, S. P. (2009). publCIF. In preparation.
In the past few decades 1,2-fused benzimidazo heterocycles have attracted attention because of their fluorescent properties (Gokhale & Seshadri, 1987; Rajagopal & Seshadri 1991). On the other hand isoquinoline derivatives exhibit a wide range of biological effects and are of great interest to synthetic as well as pharmaceutical organic chemists (Shamma, 1972; Kametami & Fukomoto, 1981; Bijan & Basu, 1965; Neumeyer & Weinhard, 1970).
In a previous paper (Volovnenko et al., 2006) we have described the synthesis of a series of 14-arylbenzimidazo[1,2-a]benzo[f]-1,8-naphthyridine-6-carbonitriles. We report herein the crystal structure of the title compound, which is the derivative of the new heterocyclic system, benzimidazo[1,2-a]benzo[f]-1,8-naphthyridine.
The molecular structure of the title compound is illustrated in Fig. 1. The benzimidazo[1,2-a]benzo[f]-1,8-naphthyridine system is nearly planar (RMS deviation of the non-hydrogen atoms from mean plane is 0.033 Å). Benzene ring is rotated with respect to this plane (the C5—C6—C7—C23 torsion angle is -67.5 (2)°). This rotation results in the loss of conjugation between π systems of the heterocycle and benzene ring. In crystal molecules form stacked chains along the a axis (Fig. 2) due to stacking interactions between the π systems of the pentacyclic fragments. The distance between the parallel planes is 3.4186 (8) Å.