Acta Cryst. (2009). E65, o995 [ doi:10.1107/S1600536809012409 ]
There are two independent molecules in the asymmetric unit of the title compound, C18H12ClN3O. The two pyridine rings are almost coplanar [dihedral angles between the rings: 2.87 (15) and 5.36 (16)°] while the chlorophenyl rings are twisted out of the plane of the adjacent bipyridine ring by 44.1 (1) and 43.8 (1)° in the two molecules. The crystal packing is stabilized by C-H
N and C-HCl interactions.
A mixture of p-chlorobenzaldehyde (1 eq), 2-acetyl pyridine and sodium hydroxide (1.2 eq) in methanol was refluxed for 30 min. After that malanonitrile (1 eq) was added and the reaction was continued to 3 h. With the completion of the reaction (as monitored by TLC), it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuo. The crude product was chromatographed and isolated in 76% yield (90:10, petroleum ether: ethyl acetate). The compound was recrystallized in ethanol.
All H atoms were positioned geometrically (C—H=0.93–0.97 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H, 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./bt2899fig1thm.gif)
| Fig. 1. Perspective view of the molecule showing the displacement ellipsoids at 50% probability level. The H atoms are shown as small circles of arbitrary radii. |
![[Figure 2]](./bt2899fig2thm.gif)
| Fig. 2. The crystal packing of the molecules viewed down b axis. H atoms not involved in hydrogen bonding have been omitted for clarity. |
| C18H12ClN3O | F(000) = 664 |
| Mr = 321.76 | Dx = 1.375 Mg m−3 |
| Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2yb | Cell parameters from 3721 reflections |
| a = 9.5869 (5) Å | θ = 1.7–27.5° |
| b = 13.8761 (7) Å | µ = 0.25 mm−1 |
| c = 12.2124 (6) Å | T = 293 K |
| β = 106.896 (2)° | Block, colorless |
| V = 1554.47 (14) Å3 | 0.30 × 0.25 × 0.20 mm |
| Z = 4 |
| Bruker Kappa APEXII area-detector diffractometer | 6950 independent reflections |
| Radiation source: fine-focus sealed tube | 4300 reflections with I > 2σ(I) |
| graphite | Rint = 0.035 |
| ω and φ scans | θmax = 27.5°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −12→12 |
| Tmin = 0.927, Tmax = 0.951 | k = −17→17 |
| 17581 measured reflections | l = −15→15 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0461P)2 + 0.1394P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.002 |
| 6950 reflections | Δρmax = 0.24 e Å−3 |
| 417 parameters | Δρmin = −0.18 e Å−3 |
| 1 restraint | Absolute structure: Flack (1983), 3268 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.05 (6) |
| C18H12ClN3O | V = 1554.47 (14) Å3 |
| Mr = 321.76 | Z = 4 |
| Monoclinic, P21 | Mo Kα radiation |
| a = 9.5869 (5) Å | µ = 0.25 mm−1 |
| b = 13.8761 (7) Å | T = 293 K |
| c = 12.2124 (6) Å | 0.30 × 0.25 × 0.20 mm |
| β = 106.896 (2)° |
| Bruker Kappa APEXII area-detector diffractometer | 6950 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 4300 reflections with I > 2σ(I) |
| Tmin = 0.927, Tmax = 0.951 | Rint = 0.035 |
| 17581 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.113 | Δρmax = 0.24 e Å−3 |
| S = 1.00 | Δρmin = −0.18 e Å−3 |
| 6950 reflections | Absolute structure: Flack (1983), 3268 Friedel pairs |
| 417 parameters | Flack parameter: 0.05 (6) |
| 1 restraint |
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 | ||
| C2' | −0.0524 (3) | 0.2747 (2) | 0.5616 (2) | 0.0453 (7) | |
| C2 | −0.1641 (3) | 0.5282 (2) | 0.7627 (2) | 0.0485 (7) | |
| C3' | 0.0529 (3) | 0.2755 (2) | 0.66886 (19) | 0.0438 (6) | |
| C3 | −0.0610 (3) | 0.5309 (2) | 0.86978 (19) | 0.0448 (6) | |
| C4' | 0.1994 (3) | 0.2704 (2) | 0.67256 (19) | 0.0450 (6) | |
| C4 | 0.0852 (3) | 0.53628 (19) | 0.87589 (19) | 0.0427 (6) | |
| C5 | 0.1208 (3) | 0.5349 (2) | 0.77260 (19) | 0.0452 (6) | |
| H5 | 0.2177 | 0.5373 | 0.7726 | 0.054* | |
| C5' | 0.2306 (3) | 0.2696 (2) | 0.56900 (19) | 0.0467 (6) | |
| H5' | 0.3271 | 0.2672 | 0.5679 | 0.056* | |
| C6 | 0.0109 (3) | 0.5301 (2) | 0.6710 (2) | 0.0439 (6) | |
| C6' | 0.1199 (3) | 0.2723 (2) | 0.4671 (2) | 0.0430 (6) | |
| C7' | −0.3014 (3) | 0.2777 (3) | 0.4542 (2) | 0.0730 (9) | |
| H7D | −0.2843 | 0.3307 | 0.4092 | 0.110* | |
| H7F | −0.3957 | 0.2845 | 0.4658 | 0.110* | |
| H7E | −0.2977 | 0.2183 | 0.4147 | 0.110* | |
| C7 | −0.4109 (3) | 0.5274 (3) | 0.6510 (2) | 0.0769 (10) | |
| H7A | −0.3862 | 0.5766 | 0.6046 | 0.115* | |
| H7B | −0.5054 | 0.5407 | 0.6598 | 0.115* | |
| H7C | −0.4125 | 0.4659 | 0.6147 | 0.115* | |
| C8' | 0.0057 (3) | 0.2856 (2) | 0.7694 (2) | 0.0506 (7) | |
| C8 | −0.1112 (3) | 0.5223 (2) | 0.9698 (2) | 0.0509 (7) | |
| C10 | 0.2010 (3) | 0.5420 (2) | 0.9863 (2) | 0.0452 (7) | |
| C10' | 0.3164 (3) | 0.2671 (2) | 0.78201 (19) | 0.0451 (6) | |
| C11 | 0.1893 (3) | 0.6056 (2) | 1.0710 (2) | 0.0488 (7) | |
| H11 | 0.1081 | 0.6455 | 1.0575 | 0.059* | |
| C11' | 0.3071 (3) | 0.2046 (2) | 0.8686 (2) | 0.0540 (7) | |
| H11' | 0.2262 | 0.1646 | 0.8573 | 0.065* | |
| C12' | 0.4158 (3) | 0.2011 (2) | 0.9709 (2) | 0.0601 (8) | |
| H12' | 0.4089 | 0.1587 | 1.0281 | 0.072* | |
| C12 | 0.2950 (3) | 0.6106 (2) | 1.1738 (2) | 0.0540 (7) | |
| H12 | 0.2867 | 0.6538 | 1.2298 | 0.065* | |
| C13' | 0.5332 (3) | 0.2601 (3) | 0.9877 (2) | 0.0609 (9) | |
| C13 | 0.4138 (3) | 0.5507 (3) | 1.1932 (2) | 0.0565 (8) | |
| C14 | 0.4309 (3) | 0.4900 (3) | 1.1102 (2) | 0.0646 (9) | |
| H14 | 0.5141 | 0.4520 | 1.1233 | 0.078* | |
| C14' | 0.5486 (3) | 0.3210 (3) | 0.9047 (3) | 0.0661 (9) | |
| H14' | 0.6307 | 0.3600 | 0.9172 | 0.079* | |
| C15' | 0.4401 (3) | 0.3240 (2) | 0.8012 (2) | 0.0567 (8) | |
| H15' | 0.4504 | 0.3648 | 0.7436 | 0.068* | |
| C15 | 0.3241 (3) | 0.4854 (2) | 1.0067 (2) | 0.0572 (8) | |
| H15 | 0.3351 | 0.4438 | 0.9501 | 0.069* | |
| C16 | 0.0424 (3) | 0.5259 (2) | 0.5593 (2) | 0.0454 (7) | |
| C16' | 0.1494 (3) | 0.2756 (2) | 0.3547 (2) | 0.0464 (6) | |
| C18' | 0.3136 (4) | 0.2815 (3) | 0.2542 (3) | 0.0821 (11) | |
| H18' | 0.4099 | 0.2807 | 0.2524 | 0.098* | |
| C18 | 0.2082 (4) | 0.5207 (3) | 0.4595 (3) | 0.0717 (10) | |
| H18 | 0.3052 | 0.5202 | 0.4594 | 0.086* | |
| C19 | 0.1032 (4) | 0.5161 (2) | 0.3559 (3) | 0.0662 (10) | |
| H19 | 0.1284 | 0.5128 | 0.2880 | 0.079* | |
| C19' | 0.2062 (4) | 0.2900 (3) | 0.1528 (2) | 0.0715 (10) | |
| H19' | 0.2299 | 0.2950 | 0.0844 | 0.086* | |
| C20' | 0.0658 (4) | 0.2910 (3) | 0.1527 (2) | 0.0643 (9) | |
| H20' | −0.0091 | 0.2968 | 0.0848 | 0.077* | |
| C20 | −0.0384 (4) | 0.5166 (3) | 0.3552 (2) | 0.0629 (9) | |
| H20 | −0.1127 | 0.5133 | 0.2866 | 0.075* | |
| C21 | −0.0705 (3) | 0.5222 (2) | 0.4585 (2) | 0.0554 (7) | |
| H21 | −0.1668 | 0.5236 | 0.4601 | 0.067* | |
| C21' | 0.0364 (3) | 0.2832 (2) | 0.2554 (2) | 0.0550 (8) | |
| H21' | −0.0596 | 0.2831 | 0.2581 | 0.066* | |
| N1 | −0.1311 (2) | 0.52769 (17) | 0.66537 (16) | 0.0476 (6) | |
| N1' | −0.0218 (2) | 0.27322 (17) | 0.46358 (16) | 0.0477 (5) | |
| N9' | −0.0333 (3) | 0.2959 (2) | 0.8486 (2) | 0.0696 (8) | |
| N9 | −0.1527 (3) | 0.5130 (2) | 1.0466 (2) | 0.0711 (8) | |
| N17' | 0.2879 (3) | 0.2742 (2) | 0.35573 (18) | 0.0655 (7) | |
| N17 | 0.1810 (3) | 0.5257 (2) | 0.56052 (18) | 0.0594 (7) | |
| O1 | −0.3049 (2) | 0.52612 (18) | 0.76094 (15) | 0.0623 (6) | |
| O1' | −0.1919 (2) | 0.27689 (18) | 0.56248 (16) | 0.0617 (6) | |
| Cl1' | 0.66572 (10) | 0.25841 (9) | 1.11925 (7) | 0.0970 (4) | |
| Cl1 | 0.54493 (9) | 0.55353 (8) | 1.32596 (6) | 0.0888 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C2' | 0.0455 (16) | 0.0402 (16) | 0.0507 (15) | −0.0023 (15) | 0.0149 (12) | 0.0032 (13) |
| C2 | 0.0441 (15) | 0.0460 (17) | 0.0545 (15) | −0.0014 (14) | 0.0130 (12) | 0.0042 (14) |
| C3' | 0.0524 (16) | 0.0416 (16) | 0.0372 (13) | −0.0055 (15) | 0.0126 (11) | 0.0029 (14) |
| C3 | 0.0522 (16) | 0.0423 (15) | 0.0408 (13) | 0.0036 (14) | 0.0149 (11) | 0.0003 (13) |
| C4' | 0.0522 (15) | 0.0395 (15) | 0.0422 (13) | −0.0043 (15) | 0.0121 (11) | 0.0023 (14) |
| C4 | 0.0472 (15) | 0.0382 (15) | 0.0422 (13) | 0.0042 (13) | 0.0120 (11) | −0.0021 (13) |
| C5 | 0.0436 (14) | 0.0473 (16) | 0.0448 (13) | 0.0024 (13) | 0.0130 (10) | −0.0011 (13) |
| C5' | 0.0505 (15) | 0.0454 (16) | 0.0433 (13) | 0.0005 (14) | 0.0122 (11) | 0.0043 (13) |
| C6 | 0.0504 (16) | 0.0392 (15) | 0.0416 (13) | −0.0009 (13) | 0.0128 (11) | −0.0008 (13) |
| C6' | 0.0496 (16) | 0.0355 (14) | 0.0427 (13) | 0.0009 (14) | 0.0113 (11) | 0.0023 (13) |
| C7' | 0.0506 (17) | 0.090 (3) | 0.0700 (19) | 0.002 (2) | 0.0034 (14) | 0.000 (2) |
| C7 | 0.0470 (17) | 0.102 (3) | 0.074 (2) | −0.010 (2) | 0.0058 (14) | 0.011 (2) |
| C8' | 0.0565 (18) | 0.0444 (19) | 0.0512 (16) | −0.0023 (16) | 0.0161 (14) | 0.0052 (14) |
| C8 | 0.0524 (16) | 0.0514 (18) | 0.0482 (15) | 0.0058 (15) | 0.0137 (12) | −0.0002 (15) |
| C10 | 0.0432 (15) | 0.0486 (17) | 0.0427 (13) | −0.0014 (14) | 0.0108 (11) | 0.0027 (14) |
| C10' | 0.0512 (15) | 0.0468 (15) | 0.0377 (12) | −0.0019 (14) | 0.0135 (10) | −0.0030 (13) |
| C11 | 0.0535 (17) | 0.0529 (17) | 0.0414 (14) | 0.0028 (14) | 0.0159 (12) | −0.0007 (13) |
| C11' | 0.0587 (18) | 0.0557 (18) | 0.0451 (15) | −0.0016 (14) | 0.0110 (12) | 0.0012 (14) |
| C12' | 0.068 (2) | 0.066 (2) | 0.0444 (15) | 0.0144 (17) | 0.0133 (14) | 0.0025 (15) |
| C12 | 0.0605 (18) | 0.0609 (19) | 0.0416 (14) | −0.0107 (16) | 0.0167 (13) | −0.0050 (13) |
| C13' | 0.0528 (18) | 0.076 (2) | 0.0464 (15) | 0.0167 (18) | 0.0034 (13) | −0.0115 (17) |
| C13 | 0.0516 (17) | 0.069 (2) | 0.0411 (14) | −0.0138 (17) | 0.0015 (12) | 0.0058 (16) |
| C14 | 0.0552 (19) | 0.068 (2) | 0.0638 (19) | 0.0076 (17) | 0.0063 (16) | 0.0046 (18) |
| C14' | 0.0426 (17) | 0.078 (2) | 0.074 (2) | −0.0076 (16) | 0.0120 (16) | −0.0202 (19) |
| C15' | 0.0550 (18) | 0.060 (2) | 0.0569 (17) | −0.0061 (15) | 0.0200 (14) | −0.0035 (15) |
| C15 | 0.0569 (18) | 0.057 (2) | 0.0541 (16) | 0.0098 (15) | 0.0107 (14) | −0.0035 (15) |
| C16 | 0.0549 (17) | 0.0386 (16) | 0.0418 (14) | −0.0049 (15) | 0.0124 (12) | −0.0012 (13) |
| C16' | 0.0569 (16) | 0.0394 (15) | 0.0427 (13) | −0.0013 (15) | 0.0143 (11) | −0.0003 (13) |
| C18' | 0.076 (2) | 0.122 (3) | 0.0567 (18) | 0.010 (2) | 0.0321 (16) | 0.009 (2) |
| C18 | 0.077 (2) | 0.083 (3) | 0.065 (2) | −0.008 (2) | 0.0367 (18) | −0.004 (2) |
| C19 | 0.097 (3) | 0.059 (2) | 0.0525 (18) | −0.012 (2) | 0.0378 (18) | −0.0001 (16) |
| C19' | 0.094 (3) | 0.081 (3) | 0.0451 (16) | 0.003 (2) | 0.0294 (17) | 0.0030 (18) |
| C20' | 0.083 (2) | 0.065 (2) | 0.0393 (15) | −0.0019 (19) | 0.0100 (15) | −0.0059 (16) |
| C20 | 0.085 (2) | 0.058 (2) | 0.0422 (16) | −0.0044 (19) | 0.0135 (16) | 0.0041 (15) |
| C21 | 0.0601 (18) | 0.0571 (19) | 0.0465 (15) | 0.0019 (16) | 0.0113 (12) | 0.0031 (14) |
| C21' | 0.0580 (17) | 0.062 (2) | 0.0438 (15) | −0.0013 (16) | 0.0121 (12) | −0.0027 (15) |
| N1 | 0.0496 (13) | 0.0515 (15) | 0.0400 (11) | −0.0026 (12) | 0.0102 (9) | 0.0012 (11) |
| N1' | 0.0509 (13) | 0.0470 (13) | 0.0436 (12) | −0.0002 (13) | 0.0113 (10) | 0.0018 (11) |
| N9' | 0.093 (2) | 0.0659 (19) | 0.0600 (16) | −0.0049 (15) | 0.0382 (15) | 0.0010 (14) |
| N9 | 0.0778 (18) | 0.084 (2) | 0.0598 (15) | 0.0023 (16) | 0.0336 (13) | −0.0006 (15) |
| N17' | 0.0601 (16) | 0.089 (2) | 0.0499 (13) | 0.0088 (17) | 0.0201 (11) | 0.0099 (15) |
| N17 | 0.0592 (15) | 0.0710 (18) | 0.0500 (13) | −0.0052 (15) | 0.0190 (11) | −0.0064 (14) |
| O1 | 0.0460 (11) | 0.0844 (17) | 0.0555 (11) | −0.0024 (12) | 0.0132 (9) | 0.0104 (12) |
| O1' | 0.0462 (11) | 0.0785 (16) | 0.0605 (12) | 0.0000 (12) | 0.0160 (9) | −0.0005 (12) |
| Cl1' | 0.0709 (5) | 0.1312 (9) | 0.0664 (5) | 0.0322 (6) | −0.0157 (4) | −0.0216 (6) |
| Cl1 | 0.0726 (5) | 0.1207 (8) | 0.0551 (4) | −0.0156 (5) | −0.0101 (3) | 0.0127 (5) |
| C2'—N1' | 1.313 (3) | C11—H11 | 0.9300 |
| C2'—O1' | 1.341 (3) | C11'—C12' | 1.375 (3) |
| C2'—C3' | 1.403 (3) | C11'—H11' | 0.9300 |
| C2—N1 | 1.316 (3) | C12'—C13' | 1.358 (5) |
| C2—O1 | 1.344 (3) | C12'—H12' | 0.9300 |
| C2—C3 | 1.391 (3) | C12—C13 | 1.374 (4) |
| C3'—C4' | 1.394 (3) | C12—H12 | 0.9300 |
| C3'—C8' | 1.433 (4) | C13'—C14' | 1.361 (5) |
| C3—C4 | 1.384 (3) | C13'—Cl1' | 1.735 (3) |
| C3—C8 | 1.442 (4) | C13—C14 | 1.364 (4) |
| C4'—C5' | 1.382 (3) | C13—Cl1 | 1.739 (3) |
| C4'—C10' | 1.475 (3) | C14—C15 | 1.378 (4) |
| C4—C5 | 1.399 (3) | C14—H14 | 0.9300 |
| C4—C10 | 1.478 (3) | C14'—C15' | 1.384 (4) |
| C5—C6 | 1.376 (3) | C14'—H14' | 0.9300 |
| C5—H5 | 0.9300 | C15'—H15' | 0.9300 |
| C5'—C6' | 1.382 (3) | C15—H15 | 0.9300 |
| C5'—H5' | 0.9300 | C16—N17 | 1.324 (3) |
| C6—N1 | 1.343 (3) | C16—C21 | 1.384 (3) |
| C6—C16 | 1.481 (3) | C16'—N17' | 1.325 (3) |
| C6'—N1' | 1.346 (3) | C16'—C21' | 1.376 (3) |
| C6'—C16' | 1.481 (3) | C18'—N17' | 1.337 (4) |
| C7'—O1' | 1.430 (3) | C18'—C19' | 1.366 (4) |
| C7'—H7D | 0.9600 | C18'—H18' | 0.9300 |
| C7'—H7F | 0.9600 | C18—N17 | 1.335 (3) |
| C7'—H7E | 0.9600 | C18—C19 | 1.370 (4) |
| C7—O1 | 1.430 (3) | C18—H18 | 0.9300 |
| C7—H7A | 0.9600 | C19—C20 | 1.355 (4) |
| C7—H7B | 0.9600 | C19—H19 | 0.9300 |
| C7—H7C | 0.9600 | C19'—C20' | 1.346 (4) |
| C8'—N9' | 1.143 (4) | C19'—H19' | 0.9300 |
| C8—N9 | 1.127 (3) | C20'—C21' | 1.367 (4) |
| C10—C15 | 1.379 (4) | C20'—H20' | 0.9300 |
| C10—C11 | 1.388 (4) | C20—C21 | 1.384 (4) |
| C10'—C15' | 1.387 (4) | C20—H20 | 0.9300 |
| C10'—C11' | 1.391 (4) | C21—H21 | 0.9300 |
| C11—C12 | 1.368 (4) | C21'—H21' | 0.9300 |
| N1'—C2'—O1' | 119.7 (2) | C11'—C12'—H12' | 120.3 |
| N1'—C2'—C3' | 124.1 (2) | C11—C12—C13 | 118.9 (3) |
| O1'—C2'—C3' | 116.2 (2) | C11—C12—H12 | 120.5 |
| N1—C2—O1 | 119.3 (2) | C13—C12—H12 | 120.5 |
| N1—C2—C3 | 123.9 (2) | C12'—C13'—C14' | 121.7 (3) |
| O1—C2—C3 | 116.8 (2) | C12'—C13'—Cl1' | 118.9 (3) |
| C4'—C3'—C2' | 118.4 (2) | C14'—C13'—Cl1' | 119.3 (3) |
| C4'—C3'—C8' | 122.9 (2) | C14—C13—C12 | 121.2 (2) |
| C2'—C3'—C8' | 118.7 (2) | C14—C13—Cl1 | 119.8 (3) |
| C4—C3—C2 | 118.9 (2) | C12—C13—Cl1 | 119.0 (2) |
| C4—C3—C8 | 122.8 (2) | C13—C14—C15 | 119.5 (3) |
| C2—C3—C8 | 118.2 (2) | C13—C14—H14 | 120.2 |
| C5'—C4'—C3' | 117.0 (2) | C15—C14—H14 | 120.2 |
| C5'—C4'—C10' | 121.3 (2) | C13'—C14'—C15' | 118.9 (3) |
| C3'—C4'—C10' | 121.6 (2) | C13'—C14'—H14' | 120.5 |
| C3—C4—C5 | 117.3 (2) | C15'—C14'—H14' | 120.5 |
| C3—C4—C10 | 122.1 (2) | C14'—C15'—C10' | 121.0 (3) |
| C5—C4—C10 | 120.5 (2) | C14'—C15'—H15' | 119.5 |
| C6—C5—C4 | 119.4 (2) | C10'—C15'—H15' | 119.5 |
| C6—C5—H5 | 120.3 | C14—C15—C10 | 120.6 (3) |
| C4—C5—H5 | 120.3 | C14—C15—H15 | 119.7 |
| C4'—C5'—C6' | 120.7 (2) | C10—C15—H15 | 119.7 |
| C4'—C5'—H5' | 119.7 | N17—C16—C21 | 122.2 (2) |
| C6'—C5'—H5' | 119.7 | N17—C16—C6 | 117.5 (2) |
| N1—C6—C5 | 123.1 (2) | C21—C16—C6 | 120.3 (2) |
| N1—C6—C16 | 115.3 (2) | N17'—C16'—C21' | 122.7 (2) |
| C5—C6—C16 | 121.6 (2) | N17'—C16'—C6' | 116.9 (2) |
| N1'—C6'—C5' | 122.2 (2) | C21'—C16'—C6' | 120.4 (3) |
| N1'—C6'—C16' | 115.6 (2) | N17'—C18'—C19' | 123.6 (3) |
| C5'—C6'—C16' | 122.1 (2) | N17'—C18'—H18' | 118.2 |
| O1'—C7'—H7D | 109.5 | C19'—C18'—H18' | 118.2 |
| O1'—C7'—H7F | 109.5 | N17—C18—C19 | 124.5 (3) |
| H7D—C7'—H7F | 109.5 | N17—C18—H18 | 117.7 |
| O1'—C7'—H7E | 109.5 | C19—C18—H18 | 117.7 |
| H7D—C7'—H7E | 109.5 | C20—C19—C18 | 118.1 (3) |
| H7F—C7'—H7E | 109.5 | C20—C19—H19 | 120.9 |
| O1—C7—H7A | 109.5 | C18—C19—H19 | 120.9 |
| O1—C7—H7B | 109.5 | C20'—C19'—C18' | 119.5 (3) |
| H7A—C7—H7B | 109.5 | C20'—C19'—H19' | 120.3 |
| O1—C7—H7C | 109.5 | C18'—C19'—H19' | 120.3 |
| H7A—C7—H7C | 109.5 | C19'—C20'—C21' | 118.1 (3) |
| H7B—C7—H7C | 109.5 | C19'—C20'—H20' | 120.9 |
| N9'—C8'—C3' | 178.3 (4) | C21'—C20'—H20' | 120.9 |
| N9—C8—C3 | 177.9 (3) | C19—C20—C21 | 118.8 (3) |
| C15—C10—C11 | 118.5 (2) | C19—C20—H20 | 120.6 |
| C15—C10—C4 | 120.7 (2) | C21—C20—H20 | 120.6 |
| C11—C10—C4 | 120.8 (2) | C16—C21—C20 | 119.3 (3) |
| C15'—C10'—C11' | 117.9 (2) | C16—C21—H21 | 120.4 |
| C15'—C10'—C4' | 121.6 (2) | C20—C21—H21 | 120.4 |
| C11'—C10'—C4' | 120.6 (2) | C20'—C21'—C16' | 119.7 (3) |
| C12—C11—C10 | 121.2 (3) | C20'—C21'—H21' | 120.2 |
| C12—C11—H11 | 119.4 | C16'—C21'—H21' | 120.2 |
| C10—C11—H11 | 119.4 | C2—N1—C6 | 117.4 (2) |
| C12'—C11'—C10' | 120.9 (3) | C2'—N1'—C6' | 117.50 (19) |
| C12'—C11'—H11' | 119.6 | C16'—N17'—C18' | 116.4 (3) |
| C10'—C11'—H11' | 119.6 | C16—N17—C18 | 117.1 (2) |
| C13'—C12'—C11' | 119.5 (3) | C2—O1—C7 | 116.9 (2) |
| C13'—C12'—H12' | 120.3 | C2'—O1'—C7' | 117.3 (2) |
| N1'—C2'—C3'—C4' | −2.8 (5) | C12—C13—C14—C15 | −3.0 (5) |
| O1'—C2'—C3'—C4' | 178.1 (3) | Cl1—C13—C14—C15 | 177.6 (2) |
| N1'—C2'—C3'—C8' | 174.6 (3) | C12'—C13'—C14'—C15' | 1.2 (5) |
| O1'—C2'—C3'—C8' | −4.5 (4) | Cl1'—C13'—C14'—C15' | −178.0 (2) |
| N1—C2—C3—C4 | 2.0 (4) | C13'—C14'—C15'—C10' | 0.8 (5) |
| O1—C2—C3—C4 | −178.0 (3) | C11'—C10'—C15'—C14' | −2.1 (4) |
| N1—C2—C3—C8 | −174.4 (3) | C4'—C10'—C15'—C14' | 179.4 (3) |
| O1—C2—C3—C8 | 5.6 (4) | C13—C14—C15—C10 | 0.5 (5) |
| C2'—C3'—C4'—C5' | 3.1 (4) | C11—C10—C15—C14 | 1.8 (4) |
| C8'—C3'—C4'—C5' | −174.2 (3) | C4—C10—C15—C14 | −179.2 (3) |
| C2'—C3'—C4'—C10' | −177.7 (3) | N1—C6—C16—N17 | −178.4 (3) |
| C8'—C3'—C4'—C10' | 5.1 (5) | C5—C6—C16—N17 | 0.8 (4) |
| C2—C3—C4—C5 | −2.4 (4) | N1—C6—C16—C21 | 1.6 (4) |
| C8—C3—C4—C5 | 173.8 (3) | C5—C6—C16—C21 | −179.2 (3) |
| C2—C3—C4—C10 | 178.3 (3) | N1'—C6'—C16'—N17' | −179.6 (3) |
| C8—C3—C4—C10 | −5.4 (4) | C5'—C6'—C16'—N17' | 1.2 (4) |
| C3—C4—C5—C6 | 1.1 (4) | N1'—C6'—C16'—C21' | 2.5 (4) |
| C10—C4—C5—C6 | −179.6 (3) | C5'—C6'—C16'—C21' | −176.7 (3) |
| C3'—C4'—C5'—C6' | −1.0 (4) | N17—C18—C19—C20 | −0.1 (6) |
| C10'—C4'—C5'—C6' | 179.7 (3) | N17'—C18'—C19'—C20' | −0.2 (7) |
| C4—C5—C6—N1 | 0.8 (4) | C18'—C19'—C20'—C21' | −0.1 (6) |
| C4—C5—C6—C16 | −178.3 (3) | C18—C19—C20—C21 | 0.3 (5) |
| C4'—C5'—C6'—N1' | −1.8 (4) | N17—C16—C21—C20 | 1.1 (5) |
| C4'—C5'—C6'—C16' | 177.4 (3) | C6—C16—C21—C20 | −178.9 (3) |
| C4'—C3'—C8'—N9' | 116 (12) | C19—C20—C21—C16 | −0.8 (5) |
| C2'—C3'—C8'—N9' | −62 (12) | C19'—C20'—C21'—C16' | 0.6 (5) |
| C4—C3—C8—N9 | −124 (9) | N17'—C16'—C21'—C20' | −0.9 (5) |
| C2—C3—C8—N9 | 52 (9) | C6'—C16'—C21'—C20' | 176.8 (3) |
| C3—C4—C10—C15 | 134.3 (3) | O1—C2—N1—C6 | 179.8 (3) |
| C5—C4—C10—C15 | −45.0 (4) | C3—C2—N1—C6 | −0.2 (4) |
| C3—C4—C10—C11 | −46.8 (4) | C5—C6—N1—C2 | −1.2 (4) |
| C5—C4—C10—C11 | 134.0 (3) | C16—C6—N1—C2 | 177.9 (2) |
| C5'—C4'—C10'—C15' | 45.0 (4) | O1'—C2'—N1'—C6' | 179.2 (3) |
| C3'—C4'—C10'—C15' | −134.2 (3) | C3'—C2'—N1'—C6' | 0.1 (5) |
| C5'—C4'—C10'—C11' | −133.5 (3) | C5'—C6'—N1'—C2' | 2.2 (4) |
| C3'—C4'—C10'—C11' | 47.3 (4) | C16'—C6'—N1'—C2' | −177.0 (2) |
| C15—C10—C11—C12 | −1.8 (4) | C21'—C16'—N17'—C18' | 0.6 (5) |
| C4—C10—C11—C12 | 179.2 (3) | C6'—C16'—N17'—C18' | −177.2 (3) |
| C15'—C10'—C11'—C12' | 1.4 (4) | C19'—C18'—N17'—C16' | 0.0 (6) |
| C4'—C10'—C11'—C12' | 179.9 (3) | C21—C16—N17—C18 | −0.8 (5) |
| C10'—C11'—C12'—C13' | 0.5 (4) | C6—C16—N17—C18 | 179.2 (3) |
| C10—C11—C12—C13 | −0.6 (4) | C19—C18—N17—C16 | 0.3 (6) |
| C11'—C12'—C13'—C14' | −1.9 (5) | N1—C2—O1—C7 | −2.6 (4) |
| C11'—C12'—C13'—Cl1' | 177.3 (2) | C3—C2—O1—C7 | 177.5 (3) |
| C11—C12—C13—C14 | 3.0 (5) | N1'—C2'—O1'—C7' | −0.1 (4) |
| C11—C12—C13—Cl1 | −177.5 (2) | C3'—C2'—O1'—C7' | 179.1 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C11—H11···N9'i | 0.93 | 2.58 | 3.321 (4) | 137 |
| C21—H21···Cl1ii | 0.93 | 2.80 | 3.597 (3) | 144 |
| C11'—H11'···N9iii | 0.93 | 2.60 | 3.349 (4) | 138 |
| C21'—H21'···Cl1'ii | 0.93 | 2.71 | 3.475 (3) | 140 |
| Symmetry codes: (i) −x, y+1/2, −z+2; (ii) x−1, y, z−1; (iii) −x, y−1/2, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C11—H11···N9'i | 0.93 | 2.58 | 3.321 (4) | 137 |
| C21—H21···Cl1ii | 0.93 | 2.80 | 3.597 (3) | 144 |
| C11'—H11'···N9iii | 0.93 | 2.60 | 3.349 (4) | 138 |
| C21'—H21'···Cl1'ii | 0.93 | 2.71 | 3.475 (3) | 140 |
| Symmetry codes: (i) −x, y+1/2, −z+2; (ii) x−1, y, z−1; (iii) −x, y−1/2, −z+2. |
PR thanks Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.
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Pyridine derivatives possess phosphodiesterase inhibiting (Heintzelman et al., 2003a,b), antifungal (Cook et al., 2004a,b), antifertility (Upton et al.,2000) and antiarrhythmic activities (Ellefson et al., 1978). The crystallographic study was useful to ascertain the molecular conformation.
The ORTEP plot of the molecule is shown in Fig.1. There are two crystallographically independent molecules in the asymmetric unit. The two pyridine rings lie in the same plane which is evidenced from the dihedral angles of 2.87 (15)° and 5.36 (16)° for the molecules 1 & 2 respectively. The planar chlorophenyl rings are twisted away from the bipyridine ring by 44.1 (1)° for (molecule 1) and 43.8 (1)° for (molecule 2), respectively. The bond angles of C3—C8—N9 (177.9 (4))° and C3'-C8'-N9' (178.3 (3))° show linearity of the cyano group, a feature observed in carbonitrile compounds.
The crystal packing is controlled by C—H···N and C—H···Cl intermolecular interactions in addition to van der Waals forces. Atoms C11 and C11' at (x, y, z) donate one proton each to N9' (-x,+y + 1/2,-z + 2) and N9 (-x,+y - 1/2,-z + 2) which connect the molecules to form a dimer with a graph-set-motiff R22(14) (Bernstein et al., 1995). These dimers are linked through intermolecular C21—H21···Cl1 hydrogen bond chain running along c axis which is shown in Fig. 2.