Acta Cryst. (2011). E67, o1677 [ doi:10.1107/S1600536811020757 ]
The asymmetric unit of the title compound, C15H14N2, contains two molecules. The amine NH group connects two aromatic systems with similar C-N-C bond angles of 120.96 (16) and 119.75 (16)° for each independent molecule. In contrast, the dihedral angles between the benzene rings are significantly different for the two independent molecules, viz. 69.1 (2) and 79.9 (2)°.
The title compound was obtained by addition of 6.6 g of (E)-4-[(p-tolylimino)methyl]benzonitrile (30 mmol) to a solution of 4.5 g of sodiumborohydride in THF, in the stoichiometric ratio 1:4. After reacting for 5 h in an ice bath, the mixture was filtered. Good quality single crystals were obtained by slow evaporation of the filtrate over two days.
Amine H atoms H1 and H4 were found in a difference map and refined with free coordinates and Uiso(H) = 0.122 Å2. C-bonded H atoms were placed in idealized positions and refined as riding to their carrier atoms, with C—H bond lengths fixed to 0.96 (methyl), 0.97 (methylene) or 0.93 Å (aromatic), and Uiso fixed at 1.5 or 1.2 times Ueq(carrier C). Methyl H atoms are splitted over two positions, due to free rotation about C2—C1 and C27—C30 bonds. Site occupancies for each group were refined, converging to 0.64 (3)/0.36 (3) for methyl group C1 and 0.66 (3)/0.34 (3) for methyl group C30.
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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]](./bh2348fig1thm.gif)
| Fig. 1. Crystal structure of the title compound with displacement ellipsoids drawn at the 30% probability level. |
![[Figure 2]](./bh2348fig2thm.gif)
| Fig. 2. Crystal structure of the title compound with view along the a axis. Intermolecular interactions are shown as dashed lines. |
| C15H14N2 | Z = 8 |
| Mr = 222.28 | F(000) = 944 |
| Monoclinic, P21/c | Dx = 1.183 Mg m−3 |
| Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
| a = 12.485 (3) Å | θ = 2.0–27.4° |
| b = 9.112 (3) Å | µ = 0.07 mm−1 |
| c = 22.180 (6) Å | T = 293 K |
| β = 98.537 (6)° | Prism, colourless |
| V = 2495.3 (12) Å3 | 0.20 × 0.20 × 0.20 mm |
| Rigaku Mercury CCD diffractometer | 4394 independent reflections |
| Radiation source: fine-focus sealed tube | 3253 reflections with I > 2σ(I) |
| graphite | Rint = 0.049 |
| Detector resolution: 28.5714 pixels mm-1 | θmax = 25.0°, θmin = 2.8° |
| ω scans | h = −14→14 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −10→10 |
| Tmin = 0.852, Tmax = 1.000 | l = −26→26 |
| 21959 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 atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2355P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.12 | (Δ/σ)max < 0.001 |
| 4394 reflections | Δρmax = 0.13 e Å−3 |
| 317 parameters | Δρmin = −0.18 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008) |
| 0 constraints | Extinction coefficient: 0.014 (4) |
| Primary atom site location: structure-invariant direct methods |
| C15H14N2 | V = 2495.3 (12) Å3 |
| Mr = 222.28 | Z = 8 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 12.485 (3) Å | µ = 0.07 mm−1 |
| b = 9.112 (3) Å | T = 293 K |
| c = 22.180 (6) Å | 0.20 × 0.20 × 0.20 mm |
| β = 98.537 (6)° |
| Rigaku Mercury CCD diffractometer | 4394 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 3253 reflections with I > 2σ(I) |
| Tmin = 0.852, Tmax = 1.000 | Rint = 0.049 |
| 21959 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.146 | Δρmax = 0.13 e Å−3 |
| S = 1.12 | Δρmin = −0.18 e Å−3 |
| 4394 reflections | Absolute structure: ? |
| 317 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| C1 | 0.9872 (2) | 0.3906 (3) | 0.28894 (9) | 0.0798 (7) | |
| H1A | 1.0443 | 0.4621 | 0.2932 | 0.120* | 0.64 (3) |
| H1B | 1.0158 | 0.2974 | 0.3038 | 0.120* | 0.64 (3) |
| H1C | 0.9318 | 0.4211 | 0.3120 | 0.120* | 0.64 (3) |
| H1D | 1.0630 | 0.3672 | 0.2940 | 0.120* | 0.36 (3) |
| H1E | 0.9509 | 0.3241 | 0.3127 | 0.120* | 0.36 (3) |
| H1F | 0.9780 | 0.4894 | 0.3024 | 0.120* | 0.36 (3) |
| C2 | 0.93940 (16) | 0.3767 (2) | 0.22236 (9) | 0.0608 (5) | |
| C3 | 0.97256 (17) | 0.4659 (2) | 0.17850 (9) | 0.0665 (5) | |
| H3A | 1.0262 | 0.5353 | 0.1904 | 0.080* | |
| C4 | 0.92924 (16) | 0.4564 (2) | 0.11736 (9) | 0.0625 (5) | |
| H4A | 0.9538 | 0.5189 | 0.0892 | 0.075* | |
| C5 | 0.84884 (15) | 0.3534 (2) | 0.09788 (8) | 0.0536 (5) | |
| C6 | 0.81507 (15) | 0.2625 (2) | 0.14188 (8) | 0.0588 (5) | |
| H6A | 0.7616 | 0.1928 | 0.1303 | 0.071* | |
| C7 | 0.85965 (17) | 0.2745 (2) | 0.20223 (9) | 0.0629 (5) | |
| H7A | 0.8355 | 0.2119 | 0.2305 | 0.075* | |
| C8 | 0.8210 (2) | 0.4451 (2) | −0.00775 (9) | 0.0804 (7) | |
| H8A | 0.8976 | 0.4521 | −0.0106 | 0.097* | |
| H8B | 0.7972 | 0.5399 | 0.0052 | 0.097* | |
| C9 | 0.75965 (18) | 0.4082 (2) | −0.06918 (8) | 0.0626 (5) | |
| C10 | 0.6848 (2) | 0.5044 (2) | −0.09876 (10) | 0.0734 (6) | |
| H10A | 0.6720 | 0.5929 | −0.0802 | 0.088* | |
| C11 | 0.62855 (18) | 0.4722 (2) | −0.15532 (10) | 0.0727 (6) | |
| H11A | 0.5788 | 0.5389 | −0.1750 | 0.087* | |
| C12 | 0.64640 (15) | 0.3395 (2) | −0.18292 (8) | 0.0579 (5) | |
| C13 | 0.72085 (17) | 0.2422 (2) | −0.15366 (9) | 0.0655 (6) | |
| H13A | 0.7334 | 0.1533 | −0.1720 | 0.079* | |
| C14 | 0.77679 (19) | 0.2767 (2) | −0.09725 (9) | 0.0718 (6) | |
| H14A | 0.8269 | 0.2103 | −0.0777 | 0.086* | |
| C15 | 0.58706 (17) | 0.3040 (2) | −0.24151 (10) | 0.0689 (6) | |
| C16 | 0.49515 (19) | 0.2565 (3) | 0.46950 (11) | 0.0853 (7) | |
| C17 | 0.42565 (16) | 0.2503 (3) | 0.41163 (9) | 0.0661 (6) | |
| C18 | 0.40122 (17) | 0.3763 (3) | 0.37803 (9) | 0.0706 (6) | |
| H18A | 0.4282 | 0.4663 | 0.3931 | 0.085* | |
| C19 | 0.33690 (17) | 0.3687 (2) | 0.32206 (9) | 0.0658 (5) | |
| H19A | 0.3208 | 0.4542 | 0.2997 | 0.079* | |
| C20 | 0.29561 (15) | 0.2362 (2) | 0.29845 (8) | 0.0567 (5) | |
| C21 | 0.31974 (17) | 0.1112 (2) | 0.33292 (9) | 0.0709 (6) | |
| H21A | 0.2922 | 0.0214 | 0.3179 | 0.085* | |
| C22 | 0.38393 (18) | 0.1168 (3) | 0.38921 (10) | 0.0744 (6) | |
| H22A | 0.3991 | 0.0315 | 0.4119 | 0.089* | |
| C23 | 0.22708 (16) | 0.2286 (2) | 0.23680 (8) | 0.0643 (5) | |
| H23A | 0.1588 | 0.1809 | 0.2404 | 0.077* | |
| H23B | 0.2115 | 0.3271 | 0.2214 | 0.077* | |
| C24 | 0.23994 (15) | 0.14312 (19) | 0.13250 (8) | 0.0522 (5) | |
| C25 | 0.30602 (16) | 0.0980 (2) | 0.09069 (9) | 0.0622 (5) | |
| H25A | 0.3780 | 0.0742 | 0.1042 | 0.075* | |
| C26 | 0.26565 (17) | 0.0883 (2) | 0.02950 (9) | 0.0633 (5) | |
| H26A | 0.3114 | 0.0572 | 0.0026 | 0.076* | |
| C27 | 0.15952 (17) | 0.1231 (2) | 0.00676 (8) | 0.0581 (5) | |
| C28 | 0.09473 (16) | 0.1671 (2) | 0.04877 (8) | 0.0619 (5) | |
| H28A | 0.0228 | 0.1908 | 0.0352 | 0.074* | |
| C29 | 0.13339 (15) | 0.1772 (2) | 0.11060 (8) | 0.0578 (5) | |
| H29A | 0.0872 | 0.2071 | 0.1375 | 0.069* | |
| C30 | 0.1177 (2) | 0.1150 (3) | −0.06047 (9) | 0.0811 (7) | |
| H30A | 0.0513 | 0.0600 | −0.0667 | 0.122* | 0.34 (3) |
| H30B | 0.1704 | 0.0674 | −0.0812 | 0.122* | 0.34 (3) |
| H30C | 0.1046 | 0.2124 | −0.0764 | 0.122* | 0.34 (3) |
| H30D | 0.0445 | 0.1505 | −0.0678 | 0.122* | 0.66 (3) |
| H30E | 0.1195 | 0.0150 | −0.0739 | 0.122* | 0.66 (3) |
| H30F | 0.1623 | 0.1743 | −0.0825 | 0.122* | 0.66 (3) |
| H1 | 0.740 (2) | 0.293 (3) | 0.0310 (11) | 0.122* | |
| H4 | 0.354 (2) | 0.159 (3) | 0.2001 (12) | 0.122* | |
| N1 | 0.80476 (15) | 0.33596 (19) | 0.03692 (7) | 0.0656 (5) | |
| N2 | 0.54010 (17) | 0.2771 (2) | −0.28871 (9) | 0.0944 (7) | |
| N3 | 0.55062 (18) | 0.2632 (3) | 0.51543 (10) | 0.1172 (9) | |
| N4 | 0.28294 (13) | 0.14703 (19) | 0.19445 (7) | 0.0636 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0882 (16) | 0.0877 (16) | 0.0595 (13) | 0.0102 (13) | −0.0023 (12) | −0.0138 (11) |
| C2 | 0.0620 (12) | 0.0629 (12) | 0.0554 (12) | 0.0112 (10) | 0.0021 (9) | −0.0097 (10) |
| C3 | 0.0646 (13) | 0.0650 (13) | 0.0667 (13) | −0.0053 (10) | −0.0003 (10) | −0.0116 (10) |
| C4 | 0.0656 (12) | 0.0618 (12) | 0.0596 (12) | −0.0097 (10) | 0.0081 (10) | −0.0022 (9) |
| C5 | 0.0537 (11) | 0.0557 (11) | 0.0508 (11) | 0.0015 (9) | 0.0052 (8) | −0.0043 (9) |
| C6 | 0.0603 (12) | 0.0583 (12) | 0.0569 (12) | −0.0062 (9) | 0.0058 (9) | −0.0012 (9) |
| C7 | 0.0701 (13) | 0.0648 (13) | 0.0538 (12) | 0.0041 (10) | 0.0094 (10) | 0.0008 (9) |
| C8 | 0.1052 (18) | 0.0767 (15) | 0.0574 (13) | −0.0287 (13) | 0.0055 (12) | 0.0054 (11) |
| C9 | 0.0786 (14) | 0.0583 (12) | 0.0503 (11) | −0.0117 (11) | 0.0077 (10) | 0.0082 (9) |
| C10 | 0.1007 (17) | 0.0545 (12) | 0.0661 (14) | 0.0003 (12) | 0.0161 (13) | 0.0035 (10) |
| C11 | 0.0747 (14) | 0.0653 (14) | 0.0772 (15) | 0.0119 (11) | 0.0087 (12) | 0.0165 (11) |
| C12 | 0.0556 (11) | 0.0634 (13) | 0.0544 (12) | −0.0046 (10) | 0.0071 (9) | 0.0118 (9) |
| C13 | 0.0760 (14) | 0.0616 (12) | 0.0583 (12) | 0.0082 (11) | 0.0073 (10) | 0.0033 (10) |
| C14 | 0.0795 (15) | 0.0708 (14) | 0.0607 (13) | 0.0113 (11) | −0.0045 (11) | 0.0077 (11) |
| C15 | 0.0598 (12) | 0.0799 (15) | 0.0646 (14) | −0.0101 (11) | 0.0016 (11) | 0.0125 (11) |
| C16 | 0.0597 (13) | 0.130 (2) | 0.0653 (15) | 0.0097 (14) | 0.0042 (12) | −0.0150 (14) |
| C17 | 0.0509 (11) | 0.0955 (16) | 0.0517 (12) | −0.0010 (11) | 0.0069 (9) | −0.0084 (11) |
| C18 | 0.0665 (13) | 0.0782 (15) | 0.0670 (14) | −0.0130 (11) | 0.0096 (11) | −0.0159 (12) |
| C19 | 0.0714 (13) | 0.0663 (13) | 0.0599 (12) | −0.0089 (11) | 0.0099 (10) | −0.0017 (10) |
| C20 | 0.0530 (11) | 0.0674 (13) | 0.0511 (11) | −0.0063 (9) | 0.0120 (9) | −0.0053 (9) |
| C21 | 0.0746 (14) | 0.0671 (13) | 0.0684 (14) | −0.0136 (11) | 0.0024 (11) | −0.0005 (11) |
| C22 | 0.0745 (14) | 0.0821 (15) | 0.0652 (14) | 0.0006 (12) | 0.0058 (11) | 0.0120 (12) |
| C23 | 0.0615 (12) | 0.0778 (14) | 0.0533 (12) | 0.0001 (10) | 0.0068 (9) | −0.0070 (10) |
| C24 | 0.0544 (11) | 0.0540 (11) | 0.0482 (10) | −0.0010 (9) | 0.0079 (8) | −0.0002 (8) |
| C25 | 0.0555 (11) | 0.0691 (13) | 0.0621 (13) | 0.0080 (10) | 0.0094 (9) | −0.0012 (10) |
| C26 | 0.0717 (13) | 0.0656 (13) | 0.0557 (12) | 0.0034 (10) | 0.0202 (10) | −0.0024 (9) |
| C27 | 0.0667 (12) | 0.0562 (11) | 0.0515 (11) | −0.0053 (10) | 0.0089 (9) | 0.0009 (9) |
| C28 | 0.0571 (12) | 0.0709 (13) | 0.0562 (12) | −0.0011 (10) | 0.0037 (9) | 0.0017 (10) |
| C29 | 0.0526 (11) | 0.0662 (12) | 0.0556 (12) | −0.0003 (9) | 0.0108 (9) | −0.0030 (9) |
| C30 | 0.0943 (17) | 0.0935 (17) | 0.0539 (13) | −0.0065 (14) | 0.0063 (11) | −0.0026 (11) |
| N1 | 0.0718 (11) | 0.0724 (12) | 0.0503 (10) | −0.0175 (9) | 0.0019 (8) | 0.0036 (8) |
| N2 | 0.0813 (14) | 0.1146 (17) | 0.0808 (14) | −0.0171 (12) | −0.0097 (11) | 0.0060 (12) |
| N3 | 0.0791 (15) | 0.188 (3) | 0.0772 (15) | 0.0210 (16) | −0.0122 (12) | −0.0228 (15) |
| N4 | 0.0592 (10) | 0.0786 (12) | 0.0522 (10) | 0.0077 (9) | 0.0048 (8) | −0.0078 (8) |
| C1—C2 | 1.514 (2) | C16—C17 | 1.440 (3) |
| C1—H1A | 0.9600 | C17—C18 | 1.379 (3) |
| C1—H1B | 0.9600 | C17—C22 | 1.386 (3) |
| C1—H1C | 0.9600 | C18—C19 | 1.376 (3) |
| C1—H1D | 0.9600 | C18—H18A | 0.9300 |
| C1—H1E | 0.9600 | C19—C20 | 1.385 (3) |
| C1—H1F | 0.9600 | C19—H19A | 0.9300 |
| C2—C3 | 1.378 (3) | C20—C21 | 1.379 (3) |
| C2—C7 | 1.388 (3) | C20—C23 | 1.503 (2) |
| C3—C4 | 1.386 (3) | C21—C22 | 1.381 (3) |
| C3—H3A | 0.9300 | C21—H21A | 0.9300 |
| C4—C5 | 1.395 (3) | C22—H22A | 0.9300 |
| C4—H4A | 0.9300 | C23—N4 | 1.454 (2) |
| C5—N1 | 1.391 (2) | C23—H23A | 0.9700 |
| C5—C6 | 1.392 (3) | C23—H23B | 0.9700 |
| C6—C7 | 1.376 (2) | C24—C29 | 1.382 (3) |
| C6—H6A | 0.9300 | C24—C25 | 1.392 (3) |
| C7—H7A | 0.9300 | C24—N4 | 1.400 (2) |
| C8—N1 | 1.439 (3) | C25—C26 | 1.379 (2) |
| C8—C9 | 1.499 (3) | C25—H25A | 0.9300 |
| C8—H8A | 0.9700 | C26—C27 | 1.383 (3) |
| C8—H8B | 0.9700 | C26—H26A | 0.9300 |
| C9—C10 | 1.374 (3) | C27—C28 | 1.381 (3) |
| C9—C14 | 1.382 (3) | C27—C30 | 1.507 (3) |
| C10—C11 | 1.376 (3) | C28—C29 | 1.388 (2) |
| C10—H10A | 0.9300 | C28—H28A | 0.9300 |
| C11—C12 | 1.388 (3) | C29—H29A | 0.9300 |
| C11—H11A | 0.9300 | C30—H30A | 0.9600 |
| C12—C13 | 1.375 (3) | C30—H30B | 0.9600 |
| C12—C15 | 1.434 (3) | C30—H30C | 0.9600 |
| C13—C14 | 1.376 (3) | C30—H30D | 0.9600 |
| C13—H13A | 0.9300 | C30—H30E | 0.9600 |
| C14—H14A | 0.9300 | C30—H30F | 0.9600 |
| C15—N2 | 1.148 (2) | N1—H1 | 0.90 (3) |
| C16—N3 | 1.145 (3) | N4—H4 | 0.89 (3) |
| C2—C1—H1A | 109.5 | C22—C17—C16 | 119.9 (2) |
| C2—C1—H1B | 109.5 | C19—C18—C17 | 119.9 (2) |
| C2—C1—H1C | 109.5 | C19—C18—H18A | 120.1 |
| C2—C1—H1D | 109.5 | C17—C18—H18A | 120.1 |
| C2—C1—H1E | 109.5 | C18—C19—C20 | 121.3 (2) |
| H1D—C1—H1E | 109.5 | C18—C19—H19A | 119.3 |
| C2—C1—H1F | 109.5 | C20—C19—H19A | 119.3 |
| H1D—C1—H1F | 109.5 | C21—C20—C19 | 118.14 (19) |
| H1E—C1—H1F | 109.5 | C21—C20—C23 | 120.93 (18) |
| C3—C2—C7 | 116.44 (18) | C19—C20—C23 | 120.93 (18) |
| C3—C2—C1 | 121.55 (19) | C20—C21—C22 | 121.4 (2) |
| C7—C2—C1 | 122.0 (2) | C20—C21—H21A | 119.3 |
| C2—C3—C4 | 122.65 (19) | C22—C21—H21A | 119.3 |
| C2—C3—H3A | 118.7 | C21—C22—C17 | 119.5 (2) |
| C4—C3—H3A | 118.7 | C21—C22—H22A | 120.2 |
| C3—C4—C5 | 120.22 (19) | C17—C22—H22A | 120.2 |
| C3—C4—H4A | 119.9 | N4—C23—C20 | 110.39 (16) |
| C5—C4—H4A | 119.9 | N4—C23—H23A | 109.6 |
| N1—C5—C6 | 119.75 (17) | C20—C23—H23A | 109.6 |
| N1—C5—C4 | 122.71 (18) | N4—C23—H23B | 109.6 |
| C6—C5—C4 | 117.51 (17) | C20—C23—H23B | 109.6 |
| C7—C6—C5 | 120.96 (18) | H23A—C23—H23B | 108.1 |
| C7—C6—H6A | 119.5 | C29—C24—C25 | 117.85 (17) |
| C5—C6—H6A | 119.5 | C29—C24—N4 | 123.25 (17) |
| C6—C7—C2 | 122.22 (19) | C25—C24—N4 | 118.87 (17) |
| C6—C7—H7A | 118.9 | C26—C25—C24 | 120.57 (18) |
| C2—C7—H7A | 118.9 | C26—C25—H25A | 119.7 |
| N1—C8—C9 | 111.46 (17) | C24—C25—H25A | 119.7 |
| N1—C8—H8A | 109.3 | C25—C26—C27 | 122.33 (18) |
| C9—C8—H8A | 109.3 | C25—C26—H26A | 118.8 |
| N1—C8—H8B | 109.3 | C27—C26—H26A | 118.8 |
| C9—C8—H8B | 109.3 | C28—C27—C26 | 116.49 (18) |
| H8A—C8—H8B | 108.0 | C28—C27—C30 | 122.01 (19) |
| C10—C9—C14 | 118.53 (19) | C26—C27—C30 | 121.50 (19) |
| C10—C9—C8 | 120.7 (2) | C27—C28—C29 | 122.23 (18) |
| C14—C9—C8 | 120.78 (19) | C27—C28—H28A | 118.9 |
| C9—C10—C11 | 121.2 (2) | C29—C28—H28A | 118.9 |
| C9—C10—H10A | 119.4 | C24—C29—C28 | 120.53 (18) |
| C11—C10—H10A | 119.4 | C24—C29—H29A | 119.7 |
| C10—C11—C12 | 119.63 (19) | C28—C29—H29A | 119.7 |
| C10—C11—H11A | 120.2 | C27—C30—H30A | 109.5 |
| C12—C11—H11A | 120.2 | C27—C30—H30B | 109.5 |
| C13—C12—C11 | 119.65 (19) | C27—C30—H30C | 109.5 |
| C13—C12—C15 | 120.27 (19) | C27—C30—H30D | 109.5 |
| C11—C12—C15 | 120.08 (18) | C27—C30—H30E | 109.5 |
| C12—C13—C14 | 119.9 (2) | H30D—C30—H30E | 109.5 |
| C12—C13—H13A | 120.0 | C27—C30—H30F | 109.5 |
| C14—C13—H13A | 120.0 | H30D—C30—H30F | 109.5 |
| C13—C14—C9 | 121.05 (19) | H30E—C30—H30F | 109.5 |
| C13—C14—H14A | 119.5 | C5—N1—C8 | 120.96 (16) |
| C9—C14—H14A | 119.5 | C5—N1—H1 | 114.4 (17) |
| N2—C15—C12 | 179.1 (2) | C8—N1—H1 | 114.8 (17) |
| N3—C16—C17 | 179.2 (3) | C24—N4—C23 | 119.75 (16) |
| C18—C17—C22 | 119.74 (19) | C24—N4—H4 | 111.8 (17) |
| C18—C17—C16 | 120.3 (2) | C23—N4—H4 | 114.3 (18) |
| C7—C2—C3—C4 | 0.4 (3) | C18—C19—C20—C21 | 0.7 (3) |
| C1—C2—C3—C4 | −179.28 (19) | C18—C19—C20—C23 | −178.89 (18) |
| C2—C3—C4—C5 | −0.1 (3) | C19—C20—C21—C22 | −0.5 (3) |
| C3—C4—C5—N1 | −178.02 (18) | C23—C20—C21—C22 | 179.04 (18) |
| C3—C4—C5—C6 | −0.1 (3) | C20—C21—C22—C17 | −0.3 (3) |
| N1—C5—C6—C7 | 178.03 (18) | C18—C17—C22—C21 | 1.1 (3) |
| C4—C5—C6—C7 | 0.0 (3) | C16—C17—C22—C21 | −178.25 (19) |
| C5—C6—C7—C2 | 0.2 (3) | C21—C20—C23—N4 | −65.8 (2) |
| C3—C2—C7—C6 | −0.4 (3) | C19—C20—C23—N4 | 113.7 (2) |
| C1—C2—C7—C6 | 179.23 (18) | C29—C24—C25—C26 | 0.1 (3) |
| N1—C8—C9—C10 | 122.3 (2) | N4—C24—C25—C26 | 177.96 (18) |
| N1—C8—C9—C14 | −57.5 (3) | C24—C25—C26—C27 | 0.4 (3) |
| C14—C9—C10—C11 | −0.6 (3) | C25—C26—C27—C28 | −0.7 (3) |
| C8—C9—C10—C11 | 179.60 (19) | C25—C26—C27—C30 | 178.61 (19) |
| C9—C10—C11—C12 | 0.8 (3) | C26—C27—C28—C29 | 0.4 (3) |
| C10—C11—C12—C13 | −0.5 (3) | C30—C27—C28—C29 | −178.88 (19) |
| C10—C11—C12—C15 | 179.14 (19) | C25—C24—C29—C28 | −0.4 (3) |
| C11—C12—C13—C14 | 0.2 (3) | N4—C24—C29—C28 | −178.12 (17) |
| C15—C12—C13—C14 | −179.46 (18) | C27—C28—C29—C24 | 0.1 (3) |
| C12—C13—C14—C9 | −0.1 (3) | C6—C5—N1—C8 | 167.4 (2) |
| C10—C9—C14—C13 | 0.3 (3) | C4—C5—N1—C8 | −14.7 (3) |
| C8—C9—C14—C13 | −179.9 (2) | C9—C8—N1—C5 | −175.91 (19) |
| C22—C17—C18—C19 | −0.9 (3) | C29—C24—N4—C23 | −18.5 (3) |
| C16—C17—C18—C19 | 178.38 (18) | C25—C24—N4—C23 | 163.85 (19) |
| C17—C18—C19—C20 | 0.1 (3) | C20—C23—N4—C24 | −171.62 (16) |
The author is grateful to the Starter Fund of Southeast University for the purchase of the diffractometer.
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We are researching for dielectric-ferroelectric materials. Recent studies have revealed that small molecular compounds which have one or more amidogens probably have this kind of character (Chen et al., 2010). Thus, we want to find aromatic compounds containing amidogens, with the hope to obtain dielectric-ferroelectric properties (Xiong et al., 2002; Zhao et al., 2008). As part of our ongoing studies, we report here the crystal structure of the title compound. The dielectric constant of 4-[(p-tolylamino)methyl]benzonitrile as a function of temperature indicates that the permittivity is basically temperature-independent (Wang et al., 2005). After characterization of the dielectric constant, there is no dielectric anomaly observed (Ye et al., 2006). This compound thus should not be a real ferroelectrics or there may be no distinct phase transition occurring within the measured temperature range.
The asymmetric unit of the title compound contains two independent molecules (Fig. 1). The N atom connects two aromatic groups, with bond angles at N1 and N4 being 120.96 (16) and 119.75 (16)°, and the dihedral angle between two benzene rings being 69.1 (2) and 79.9 (2)°, respectively. In the crystal structure, very weak intermolecular interactions link molecules to form one-dimensional ladder propagating along the [010] direction (Fig. 2).