Acta Cryst. (2009). E65, o1308 [ doi:10.1107/S1600536809017498 ]
There are two molecules in the asymmetric unit of the title compound, C19H12N4, with dihedral angles of 2.41 (10) and 10.53 (12)° between the fused ring system and the pendant phenyl ring. In the crystal, molecules are linked into chains by N-H
N hydrogen bonds and aromatic ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking interactions [shortest centroid-centroid distance = 3.6176 (16) Å] complete the structure.
The L ligand was synthesized according to the literature method of Steck & Day (1943): a mixture of L, MnCl2 and water in a molar ratio of 2:1:5000 was sealed in a Teflon-lined autoclave and heated to 413 K for 3 d. Upon cooling and opening the bomb, accidentally, pale yellow blocks of (I) were obtained.
The H atoms were positioned geometrically (C—H = 0.93 Å, N—H = 0.86Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./hb2971fig1thm.gif)
| Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for the H atoms). |
![[Figure 2]](./hb2971fig2thm.gif)
| Fig. 2. A view of the crystal packing, showing the N—H···N hydrogen bonds and π-π stacking interactions. H atoms have been omitted. |
| C19H12N4 | Z = 4 |
| Mr = 296.33 | F000 = 616 |
| Triclinic, P1 | Dx = 1.354 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 10.016 (2) Å | Cell parameters from 3449 reflections |
| b = 12.210 (2) Å | θ = 3.0–27.5º |
| c = 12.415 (3) Å | µ = 0.08 mm−1 |
| α = 89.90 (3)º | T = 292 K |
| β = 78.44 (3)º | Block, pale yellow |
| γ = 77.96 (3)º | 0.30 × 0.25 × 0.20 mm |
| V = 1453.7 (5) Å3 |
| Rigaku R-AXIS RAPID diffractometer | 6587 independent reflections |
| Radiation source: fine-focus sealed tube | 3657 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.048 |
| Detector resolution: 10.0 pixels mm-1 | θmax = 27.5º |
| T = 292 K | θmin = 3.0º |
| ω scans | h = −12→12 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→15 |
| Tmin = 0.975, Tmax = 0.984 | l = −16→16 |
| 14453 measured reflections |
| 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)] = 0.059 | H-atom parameters constrained |
| wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0719P)2 + 0.0624P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max < 0.001 |
| 6587 reflections | Δρmax = 0.41 e Å−3 |
| 415 parameters | Δρmin = −0.20 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C19H12N4 | γ = 77.96 (3)º |
| Mr = 296.33 | V = 1453.7 (5) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 10.016 (2) Å | Mo Kα |
| b = 12.210 (2) Å | µ = 0.08 mm−1 |
| c = 12.415 (3) Å | T = 292 K |
| α = 89.90 (3)º | 0.30 × 0.25 × 0.20 mm |
| β = 78.44 (3)º |
| Rigaku R-AXIS RAPID diffractometer | 6587 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3657 reflections with I > 2σ(I) |
| Tmin = 0.975, Tmax = 0.984 | Rint = 0.048 |
| 14453 measured reflections |
| R[F2 > 2σ(F2)] = 0.059 | 415 parameters |
| wR(F2) = 0.156 | H-atom parameters constrained |
| S = 1.01 | Δρmax = 0.41 e Å−3 |
| 6587 reflections | Δρmin = −0.20 e Å−3 |
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 | −0.0622 (2) | 0.23344 (19) | 0.81330 (18) | 0.0490 (6) | |
| H1 | −0.1221 | 0.2801 | 0.8697 | 0.059* | |
| C2 | −0.0895 (2) | 0.12895 (19) | 0.79496 (18) | 0.0484 (6) | |
| H2 | −0.1658 | 0.1068 | 0.8380 | 0.058* | |
| C3 | −0.0027 (2) | 0.05936 (18) | 0.71295 (17) | 0.0450 (5) | |
| H3A | −0.0182 | −0.0115 | 0.7001 | 0.054* | |
| C4 | 0.1104 (2) | 0.09578 (17) | 0.64798 (15) | 0.0372 (5) | |
| C5 | 0.2049 (2) | 0.03323 (16) | 0.55681 (16) | 0.0389 (5) | |
| C6 | 0.3066 (2) | 0.07524 (17) | 0.48872 (16) | 0.0399 (5) | |
| C7 | 0.3291 (2) | 0.18394 (18) | 0.51052 (16) | 0.0411 (5) | |
| C8 | 0.4316 (2) | 0.2316 (2) | 0.44514 (19) | 0.0511 (6) | |
| H8 | 0.4916 | 0.1918 | 0.3843 | 0.061* | |
| C9 | 0.4418 (3) | 0.3372 (2) | 0.4723 (2) | 0.0620 (7) | |
| H9 | 0.5088 | 0.3707 | 0.4300 | 0.074* | |
| C10 | 0.3510 (3) | 0.3944 (2) | 0.5639 (2) | 0.0602 (7) | |
| H10 | 0.3590 | 0.4665 | 0.5808 | 0.072* | |
| C11 | 0.2416 (2) | 0.24813 (17) | 0.60234 (16) | 0.0396 (5) | |
| C12 | 0.1303 (2) | 0.20394 (17) | 0.67106 (15) | 0.0376 (5) | |
| C13 | 0.3167 (2) | −0.08769 (19) | 0.42188 (16) | 0.0441 (5) | |
| C14 | 0.3576 (2) | −0.1902 (2) | 0.35036 (18) | 0.0471 (6) | |
| C15 | 0.3037 (3) | −0.2845 (2) | 0.3759 (2) | 0.0621 (7) | |
| H15 | 0.2408 | −0.2852 | 0.4419 | 0.075* | |
| C16 | 0.3416 (3) | −0.3775 (2) | 0.3051 (2) | 0.0745 (8) | |
| H16 | 0.3036 | −0.4401 | 0.3231 | 0.089* | |
| C17 | 0.4350 (3) | −0.3777 (3) | 0.2086 (3) | 0.0802 (10) | |
| H17 | 0.4613 | −0.4406 | 0.1609 | 0.096* | |
| C18 | 0.4895 (3) | −0.2857 (3) | 0.1823 (2) | 0.0781 (9) | |
| H18 | 0.5529 | −0.2861 | 0.1163 | 0.094* | |
| C19 | 0.4521 (3) | −0.1917 (2) | 0.2523 (2) | 0.0631 (7) | |
| H19 | 0.4904 | −0.1295 | 0.2335 | 0.076* | |
| C20 | −0.0061 (2) | 0.71983 (19) | 0.57979 (18) | 0.0495 (6) | |
| H20 | −0.0384 | 0.7605 | 0.5233 | 0.059* | |
| C21 | −0.0429 (2) | 0.61739 (19) | 0.60084 (18) | 0.0485 (6) | |
| H21 | −0.0989 | 0.5910 | 0.5600 | 0.058* | |
| C22 | 0.0046 (2) | 0.55589 (18) | 0.68273 (17) | 0.0455 (5) | |
| H22 | −0.0169 | 0.4862 | 0.6976 | 0.055* | |
| C23 | 0.0864 (2) | 0.59938 (17) | 0.74404 (16) | 0.0382 (5) | |
| C24 | 0.1393 (2) | 0.54495 (17) | 0.83266 (16) | 0.0379 (5) | |
| C25 | 0.2102 (2) | 0.59356 (18) | 0.89767 (16) | 0.0406 (5) | |
| C26 | 0.2425 (2) | 0.70078 (18) | 0.87370 (16) | 0.0405 (5) | |
| C27 | 0.3175 (2) | 0.7535 (2) | 0.93361 (18) | 0.0510 (6) | |
| H27 | 0.3498 | 0.7192 | 0.9931 | 0.061* | |
| C28 | 0.3424 (3) | 0.8564 (2) | 0.9033 (2) | 0.0599 (7) | |
| H28 | 0.3910 | 0.8936 | 0.9423 | 0.072* | |
| C29 | 0.2938 (3) | 0.9040 (2) | 0.8131 (2) | 0.0611 (7) | |
| H29 | 0.3119 | 0.9737 | 0.7931 | 0.073* | |
| C30 | 0.1977 (2) | 0.75555 (17) | 0.78341 (16) | 0.0404 (5) | |
| C31 | 0.1167 (2) | 0.70490 (17) | 0.71880 (16) | 0.0384 (5) | |
| C32 | 0.1928 (2) | 0.43446 (18) | 0.96433 (16) | 0.0415 (5) | |
| C33 | 0.2076 (2) | 0.33528 (19) | 1.03149 (17) | 0.0447 (5) | |
| C34 | 0.1535 (3) | 0.2436 (2) | 1.0129 (2) | 0.0654 (7) | |
| H34 | 0.1045 | 0.2443 | 0.9566 | 0.078* | |
| C35 | 0.1709 (3) | 0.1517 (3) | 1.0762 (2) | 0.0797 (9) | |
| H35 | 0.1332 | 0.0908 | 1.0627 | 0.096* | |
| C36 | 0.2433 (3) | 0.1487 (3) | 1.1591 (2) | 0.0751 (8) | |
| H36 | 0.2558 | 0.0859 | 1.2015 | 0.090* | |
| C37 | 0.2964 (3) | 0.2383 (3) | 1.1787 (2) | 0.0709 (8) | |
| H37 | 0.3447 | 0.2371 | 1.2355 | 0.085* | |
| C38 | 0.2797 (3) | 0.3312 (2) | 1.11548 (19) | 0.0603 (7) | |
| H38 | 0.3174 | 0.3918 | 1.1297 | 0.072* | |
| N1 | 0.04442 (19) | 0.27076 (14) | 0.75517 (14) | 0.0444 (5) | |
| N2 | 0.2540 (2) | 0.35239 (16) | 0.62830 (15) | 0.0488 (5) | |
| N3 | 0.21246 (18) | −0.07178 (14) | 0.51377 (13) | 0.0429 (4) | |
| H3 | 0.1617 | −0.1184 | 0.5395 | 0.052* | |
| N4 | 0.37586 (19) | 0.00010 (16) | 0.40376 (14) | 0.0461 (5) | |
| N5 | 0.0722 (2) | 0.76364 (15) | 0.63503 (14) | 0.0460 (5) | |
| N6 | 0.2236 (2) | 0.85701 (16) | 0.75407 (15) | 0.0505 (5) | |
| N7 | 0.12911 (18) | 0.44362 (14) | 0.87635 (13) | 0.0403 (4) | |
| H7 | 0.0899 | 0.3947 | 0.8529 | 0.048* | |
| N8 | 0.24317 (19) | 0.52409 (15) | 0.98030 (14) | 0.0441 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0537 (14) | 0.0477 (14) | 0.0407 (12) | −0.0078 (11) | −0.0015 (11) | −0.0058 (11) |
| C2 | 0.0496 (13) | 0.0490 (14) | 0.0437 (12) | −0.0115 (11) | −0.0017 (11) | 0.0028 (11) |
| C3 | 0.0518 (13) | 0.0392 (12) | 0.0451 (12) | −0.0118 (10) | −0.0098 (11) | 0.0036 (10) |
| C4 | 0.0449 (12) | 0.0340 (11) | 0.0327 (10) | −0.0070 (9) | −0.0098 (9) | 0.0033 (9) |
| C5 | 0.0489 (12) | 0.0327 (11) | 0.0346 (11) | −0.0057 (10) | −0.0103 (10) | 0.0025 (9) |
| C6 | 0.0452 (12) | 0.0406 (12) | 0.0347 (11) | −0.0076 (10) | −0.0118 (10) | 0.0055 (9) |
| C7 | 0.0446 (12) | 0.0435 (13) | 0.0382 (11) | −0.0108 (10) | −0.0140 (10) | 0.0070 (10) |
| C8 | 0.0479 (14) | 0.0620 (16) | 0.0468 (13) | −0.0183 (12) | −0.0106 (11) | 0.0090 (11) |
| C9 | 0.0588 (16) | 0.0709 (18) | 0.0647 (16) | −0.0337 (14) | −0.0118 (13) | 0.0143 (14) |
| C10 | 0.0650 (17) | 0.0540 (16) | 0.0692 (17) | −0.0279 (13) | −0.0156 (14) | 0.0053 (13) |
| C11 | 0.0452 (12) | 0.0385 (12) | 0.0385 (11) | −0.0092 (10) | −0.0162 (10) | 0.0054 (9) |
| C12 | 0.0446 (12) | 0.0364 (11) | 0.0328 (10) | −0.0066 (9) | −0.0121 (9) | 0.0031 (9) |
| C13 | 0.0481 (13) | 0.0463 (13) | 0.0351 (11) | −0.0030 (11) | −0.0094 (10) | 0.0002 (10) |
| C14 | 0.0477 (13) | 0.0498 (14) | 0.0415 (12) | −0.0009 (11) | −0.0139 (10) | −0.0055 (11) |
| C15 | 0.0723 (17) | 0.0529 (16) | 0.0540 (15) | −0.0022 (13) | −0.0077 (13) | −0.0143 (13) |
| C16 | 0.086 (2) | 0.0588 (18) | 0.0757 (19) | −0.0058 (15) | −0.0186 (17) | −0.0197 (15) |
| C17 | 0.0701 (19) | 0.081 (2) | 0.082 (2) | 0.0056 (17) | −0.0209 (17) | −0.0417 (18) |
| C18 | 0.0578 (17) | 0.103 (3) | 0.0629 (17) | −0.0055 (17) | 0.0007 (14) | −0.0354 (18) |
| C19 | 0.0541 (15) | 0.0762 (18) | 0.0535 (15) | −0.0076 (13) | −0.0047 (12) | −0.0152 (14) |
| C20 | 0.0639 (15) | 0.0469 (14) | 0.0419 (12) | −0.0100 (12) | −0.0224 (11) | 0.0082 (10) |
| C21 | 0.0564 (14) | 0.0453 (14) | 0.0483 (13) | −0.0087 (11) | −0.0235 (11) | 0.0018 (11) |
| C22 | 0.0580 (14) | 0.0366 (12) | 0.0465 (12) | −0.0103 (11) | −0.0209 (11) | 0.0018 (10) |
| C23 | 0.0429 (12) | 0.0340 (12) | 0.0366 (11) | −0.0050 (9) | −0.0092 (9) | −0.0008 (9) |
| C24 | 0.0468 (12) | 0.0322 (11) | 0.0343 (10) | −0.0053 (9) | −0.0103 (9) | 0.0005 (9) |
| C25 | 0.0449 (12) | 0.0423 (12) | 0.0330 (11) | −0.0043 (10) | −0.0094 (9) | 0.0003 (9) |
| C26 | 0.0414 (12) | 0.0431 (13) | 0.0361 (11) | −0.0079 (10) | −0.0069 (9) | −0.0017 (9) |
| C27 | 0.0543 (14) | 0.0593 (16) | 0.0434 (13) | −0.0175 (12) | −0.0142 (11) | −0.0027 (11) |
| C28 | 0.0663 (16) | 0.0649 (17) | 0.0567 (15) | −0.0290 (14) | −0.0160 (13) | −0.0051 (13) |
| C29 | 0.0739 (18) | 0.0540 (16) | 0.0648 (16) | −0.0317 (14) | −0.0175 (14) | 0.0048 (13) |
| C30 | 0.0456 (12) | 0.0366 (12) | 0.0393 (11) | −0.0104 (10) | −0.0073 (10) | −0.0009 (9) |
| C31 | 0.0434 (12) | 0.0368 (12) | 0.0337 (11) | −0.0052 (9) | −0.0087 (9) | −0.0003 (9) |
| C32 | 0.0459 (13) | 0.0442 (13) | 0.0321 (10) | −0.0027 (10) | −0.0095 (9) | 0.0022 (9) |
| C33 | 0.0474 (13) | 0.0467 (13) | 0.0350 (11) | −0.0013 (10) | −0.0059 (10) | 0.0067 (10) |
| C34 | 0.085 (2) | 0.0583 (17) | 0.0612 (16) | −0.0206 (15) | −0.0298 (14) | 0.0237 (13) |
| C35 | 0.103 (2) | 0.0656 (19) | 0.079 (2) | −0.0267 (17) | −0.0296 (18) | 0.0329 (16) |
| C36 | 0.080 (2) | 0.070 (2) | 0.0656 (18) | −0.0016 (16) | −0.0087 (16) | 0.0328 (15) |
| C37 | 0.0715 (19) | 0.088 (2) | 0.0504 (15) | −0.0020 (17) | −0.0226 (14) | 0.0220 (15) |
| C38 | 0.0646 (17) | 0.0678 (18) | 0.0473 (14) | −0.0062 (14) | −0.0167 (12) | 0.0108 (13) |
| N1 | 0.0540 (11) | 0.0385 (10) | 0.0400 (10) | −0.0086 (9) | −0.0094 (9) | −0.0009 (8) |
| N2 | 0.0573 (12) | 0.0411 (11) | 0.0536 (11) | −0.0171 (9) | −0.0179 (9) | 0.0032 (9) |
| N3 | 0.0521 (11) | 0.0370 (10) | 0.0377 (10) | −0.0091 (8) | −0.0049 (9) | −0.0007 (8) |
| N4 | 0.0486 (11) | 0.0494 (12) | 0.0369 (9) | −0.0057 (9) | −0.0052 (8) | −0.0018 (9) |
| N5 | 0.0581 (12) | 0.0423 (11) | 0.0408 (10) | −0.0114 (9) | −0.0165 (9) | 0.0046 (8) |
| N6 | 0.0622 (13) | 0.0431 (11) | 0.0516 (11) | −0.0204 (10) | −0.0146 (10) | 0.0027 (9) |
| N7 | 0.0514 (11) | 0.0349 (10) | 0.0373 (9) | −0.0093 (8) | −0.0149 (8) | 0.0042 (8) |
| N8 | 0.0496 (11) | 0.0466 (11) | 0.0369 (9) | −0.0079 (9) | −0.0134 (8) | 0.0042 (8) |
| C1—N1 | 1.327 (3) | C20—C21 | 1.386 (3) |
| C1—C2 | 1.388 (3) | C20—H20 | 0.9300 |
| C1—H1 | 0.9300 | C21—C22 | 1.366 (3) |
| C2—C3 | 1.362 (3) | C21—H21 | 0.9300 |
| C2—H2 | 0.9300 | C22—C23 | 1.402 (3) |
| C3—C4 | 1.405 (3) | C22—H22 | 0.9300 |
| C3—H3A | 0.9300 | C23—C31 | 1.405 (3) |
| C4—C12 | 1.414 (3) | C23—C24 | 1.420 (3) |
| C4—C5 | 1.426 (3) | C24—N7 | 1.365 (3) |
| C5—N3 | 1.371 (2) | C24—C25 | 1.384 (3) |
| C5—C6 | 1.374 (3) | C25—N8 | 1.377 (3) |
| C6—N4 | 1.371 (3) | C25—C26 | 1.430 (3) |
| C6—C7 | 1.427 (3) | C26—C27 | 1.399 (3) |
| C7—C8 | 1.402 (3) | C26—C30 | 1.407 (3) |
| C7—C11 | 1.414 (3) | C27—C28 | 1.369 (3) |
| C8—C9 | 1.363 (3) | C27—H27 | 0.9300 |
| C8—H8 | 0.9300 | C28—C29 | 1.388 (4) |
| C9—C10 | 1.390 (3) | C28—H28 | 0.9300 |
| C9—H9 | 0.9300 | C29—N6 | 1.319 (3) |
| C10—N2 | 1.320 (3) | C29—H29 | 0.9300 |
| C10—H10 | 0.9300 | C30—N6 | 1.352 (3) |
| C11—N2 | 1.350 (3) | C30—C31 | 1.468 (3) |
| C11—C12 | 1.459 (3) | C31—N5 | 1.358 (3) |
| C12—N1 | 1.359 (3) | C32—N8 | 1.327 (3) |
| C13—N4 | 1.327 (3) | C32—N7 | 1.365 (3) |
| C13—N3 | 1.367 (3) | C32—C33 | 1.468 (3) |
| C13—C14 | 1.472 (3) | C33—C38 | 1.377 (3) |
| C14—C19 | 1.381 (3) | C33—C34 | 1.380 (3) |
| C14—C15 | 1.381 (3) | C34—C35 | 1.371 (4) |
| C15—C16 | 1.377 (3) | C34—H34 | 0.9300 |
| C15—H15 | 0.9300 | C35—C36 | 1.370 (4) |
| C16—C17 | 1.364 (4) | C35—H35 | 0.9300 |
| C16—H16 | 0.9300 | C36—C37 | 1.354 (4) |
| C17—C18 | 1.360 (4) | C36—H36 | 0.9300 |
| C17—H17 | 0.9300 | C37—C38 | 1.380 (4) |
| C18—C19 | 1.381 (3) | C37—H37 | 0.9300 |
| C18—H18 | 0.9300 | C38—H38 | 0.9300 |
| C19—H19 | 0.9300 | N3—H3 | 0.8600 |
| C20—N5 | 1.328 (3) | N7—H7 | 0.8600 |
| N1—C1—C2 | 123.9 (2) | C21—C22—C23 | 119.0 (2) |
| N1—C1—H1 | 118.1 | C21—C22—H22 | 120.5 |
| C2—C1—H1 | 118.1 | C23—C22—H22 | 120.5 |
| C3—C2—C1 | 118.9 (2) | C22—C23—C31 | 118.7 (2) |
| C3—C2—H2 | 120.5 | C22—C23—C24 | 124.4 (2) |
| C1—C2—H2 | 120.5 | C31—C23—C24 | 116.91 (18) |
| C2—C3—C4 | 119.3 (2) | N7—C24—C25 | 105.51 (18) |
| C2—C3—H3A | 120.3 | N7—C24—C23 | 131.11 (18) |
| C4—C3—H3A | 120.3 | C25—C24—C23 | 123.3 (2) |
| C3—C4—C12 | 118.36 (18) | N8—C25—C24 | 110.69 (19) |
| C3—C4—C5 | 124.80 (19) | N8—C25—C26 | 128.53 (19) |
| C12—C4—C5 | 116.80 (18) | C24—C25—C26 | 120.8 (2) |
| N3—C5—C6 | 105.81 (17) | C27—C26—C30 | 118.2 (2) |
| N3—C5—C4 | 130.73 (19) | C27—C26—C25 | 124.0 (2) |
| C6—C5—C4 | 123.36 (19) | C30—C26—C25 | 117.79 (19) |
| N4—C6—C5 | 110.98 (18) | C28—C27—C26 | 119.0 (2) |
| N4—C6—C7 | 128.25 (19) | C28—C27—H27 | 120.5 |
| C5—C6—C7 | 120.76 (18) | C26—C27—H27 | 120.5 |
| C8—C7—C11 | 118.0 (2) | C27—C28—C29 | 118.6 (2) |
| C8—C7—C6 | 123.79 (19) | C27—C28—H28 | 120.7 |
| C11—C7—C6 | 118.21 (19) | C29—C28—H28 | 120.7 |
| C9—C8—C7 | 118.9 (2) | N6—C29—C28 | 124.3 (2) |
| C9—C8—H8 | 120.6 | N6—C29—H29 | 117.8 |
| C7—C8—H8 | 120.6 | C28—C29—H29 | 117.8 |
| C8—C9—C10 | 119.2 (2) | N6—C30—C26 | 122.15 (19) |
| C8—C9—H9 | 120.4 | N6—C30—C31 | 117.3 (2) |
| C10—C9—H9 | 120.4 | C26—C30—C31 | 120.52 (19) |
| N2—C10—C9 | 124.0 (2) | N5—C31—C23 | 121.66 (18) |
| N2—C10—H10 | 118.0 | N5—C31—C30 | 117.79 (19) |
| C9—C10—H10 | 118.0 | C23—C31—C30 | 120.55 (19) |
| N2—C11—C7 | 122.30 (19) | N8—C32—N7 | 112.31 (19) |
| N2—C11—C12 | 117.46 (19) | N8—C32—C33 | 123.9 (2) |
| C7—C11—C12 | 120.21 (18) | N7—C32—C33 | 123.74 (19) |
| N1—C12—C4 | 121.24 (19) | C38—C33—C34 | 117.9 (2) |
| N1—C12—C11 | 118.20 (18) | C38—C33—C32 | 119.7 (2) |
| C4—C12—C11 | 120.53 (18) | C34—C33—C32 | 122.4 (2) |
| N4—C13—N3 | 112.41 (17) | C35—C34—C33 | 120.9 (3) |
| N4—C13—C14 | 123.79 (19) | C35—C34—H34 | 119.5 |
| N3—C13—C14 | 123.8 (2) | C33—C34—H34 | 119.5 |
| C19—C14—C15 | 118.4 (2) | C36—C35—C34 | 120.5 (3) |
| C19—C14—C13 | 118.8 (2) | C36—C35—H35 | 119.7 |
| C15—C14—C13 | 122.9 (2) | C34—C35—H35 | 119.7 |
| C16—C15—C14 | 121.1 (3) | C37—C36—C35 | 119.2 (3) |
| C16—C15—H15 | 119.5 | C37—C36—H36 | 120.4 |
| C14—C15—H15 | 119.5 | C35—C36—H36 | 120.4 |
| C17—C16—C15 | 119.8 (3) | C36—C37—C38 | 120.8 (3) |
| C17—C16—H16 | 120.1 | C36—C37—H37 | 119.6 |
| C15—C16—H16 | 120.1 | C38—C37—H37 | 119.6 |
| C18—C17—C16 | 119.9 (2) | C33—C38—C37 | 120.7 (3) |
| C18—C17—H17 | 120.1 | C33—C38—H38 | 119.7 |
| C16—C17—H17 | 120.1 | C37—C38—H38 | 119.7 |
| C17—C18—C19 | 120.9 (3) | C1—N1—C12 | 118.24 (18) |
| C17—C18—H18 | 119.6 | C10—N2—C11 | 117.7 (2) |
| C19—C18—H18 | 119.6 | C13—N3—C5 | 106.42 (18) |
| C14—C19—C18 | 120.0 (3) | C13—N3—H3 | 126.8 |
| C14—C19—H19 | 120.0 | C5—N3—H3 | 126.8 |
| C18—C19—H19 | 120.0 | C13—N4—C6 | 104.37 (17) |
| N5—C20—C21 | 124.2 (2) | C20—N5—C31 | 117.64 (19) |
| N5—C20—H20 | 117.9 | C29—N6—C30 | 117.6 (2) |
| C21—C20—H20 | 117.9 | C24—N7—C32 | 107.11 (17) |
| C22—C21—C20 | 118.7 (2) | C24—N7—H7 | 126.4 |
| C22—C21—H21 | 120.6 | C32—N7—H7 | 126.4 |
| C20—C21—H21 | 120.6 | C32—N8—C25 | 104.37 (17) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3···N5i | 0.86 | 2.10 | 2.932 (3) | 164 |
| N7—H7···N1 | 0.86 | 2.12 | 2.951 (2) | 163 |
| Symmetry codes: (i) x, y−1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3—H3···N5i | 0.86 | 2.10 | 2.932 (3) | 164 |
| N7—H7···N1 | 0.86 | 2.12 | 2.951 (2) | 163 |
| Symmetry codes: (i) x, y−1, z. |
The authors thank the Postdoctoral Foundation of Jiangsu Province (No. 0801010B) for support.
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Xi, H.-M. (2008). Acta Cryst. E64, o1981.
1,10-Phenanthroline (phen) or its derivatives, as an important chelating ligands with excellent coordinating abilities and fruitful aromatic systems, have been extensively used to build supramolecular architectures (Che, Liu et al., 2008; Stephenson, Hardie et al., 2006). We report here the synthesis and structure of the title compound, namely, C19H12N4 (I), using the phen derivative 2-Phenyl-1H-1,3,7,8-tetraazacyclopenta- [l]phenanthrene (L).
The asymmetric unit of (I) consists of two independent L molecules (Fig.1). The two phenyl rings are slightly twisted with respect to the fused-ring system [dihedral angles = 1.34 and 1.54 °], which is different from a related compound that has been reported (Xi, 2008). In the crystal structure, N—H···N hydrogen bonds (Table 1) link the molecules into chains along the b axis. The neighbouring chains interact through π-π contact between two L ligands [centroid separation = 3.541 Å], leading to the ultimate supramolecular structure (Fig. 2).