Acta Cryst. (2008). E64, o1782 [ doi:10.1107/S160053680802610X ]
The title compound [systematic name: 2-(1H-1,2,3-benzotriazol-1-ylmethyl)isoindole-1,3-dione], C15H10N4O2, was prepared by the reaction of 1H-benzotriazole and 2-bromomethylisoindole-1,3-dione. The benzotriazole and isoindole units are almost planar and make a dihedral angle of 70.2 (1)° (mean planes include C and N atoms). A weak C-H
O intramolecular hydrogen bond involving a carbonyl O atom as acceptor stabilizes the observed molecular conformation.
The title compound was synthesized with the following procedure: 2-bromomethyl-isoindole-1,3-dione (3.6 g, 0.015 mol) and 1H-benzotriazole (1.78 g, 0.015 mol) were dissolved in chloroform (15 ml). The solution was cooled to 283 K. Then, 1.5 g (0.015 mol) of triethylamine was added dropwise via a cannula into the well stirred solution, at 283 K. The reaction mixture was stirred at 283 K for 6 h. and at room temperature for an additional time of 16 h. Water (20 ml) was added into the solution and the resulting white solid was filtered. The organic phase was separated and dried with anhydrous potassium carbonate. The colourless organic phase was evaporated, affording (I), in 53% yield. Crystals suitable for X-ray studies were obtained from anhydrous acetone, at room temperature, after three days.
All H atoms were placed geometrically (C—H = 0.93 Å for aromatic CH, 0.97 Å for methylene CH2), and refined as riding to their parent atom with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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]](./bh2185fig1thm.gif)
| Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level. |
| C15H10N4O2 | Z = 2 |
| Mr = 278.27 | F000 = 288 |
| Triclinic, P1 | Dx = 1.459 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 6.9481 (11) Å | Cell parameters from 1689 reflections |
| b = 8.0041 (13) Å | θ = 1.7–28.2º |
| c = 12.030 (2) Å | µ = 0.10 mm−1 |
| α = 85.715 (3)º | T = 293 (2) K |
| β = 81.283 (3)º | Block, colourless |
| γ = 73.398 (3)º | 0.25 × 0.20 × 0.18 mm |
| V = 633.38 (18) Å3 |
| Bruker SMART CCD area-detector diffractometer | 1689 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.023 |
| Monochromator: graphite | θmax = 25.0º |
| T = 293(2) K | θmin = 1.7º |
| φ and ω scans | h = −7→8 |
| Absorption correction: none | k = −5→9 |
| 3364 measured reflections | l = −14→14 |
| 2229 independent reflections |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.041 | w = 1/[σ2(Fo2) + (0.0531P)2 + 0.0288P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.110 | (Δ/σ)max < 0.001 |
| S = 1.09 | Δρmax = 0.16 e Å−3 |
| 2229 reflections | Δρmin = −0.17 e Å−3 |
| 191 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.069 (7) |
| Secondary atom site location: difference Fourier map |
| C15H10N4O2 | γ = 73.398 (3)º |
| Mr = 278.27 | V = 633.38 (18) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 6.9481 (11) Å | Mo Kα |
| b = 8.0041 (13) Å | µ = 0.10 mm−1 |
| c = 12.030 (2) Å | T = 293 (2) K |
| α = 85.715 (3)º | 0.25 × 0.20 × 0.18 mm |
| β = 81.283 (3)º |
| Bruker SMART CCD area-detector diffractometer | 2229 independent reflections |
| Absorption correction: none | 1689 reflections with I > 2σ(I) |
| 3364 measured reflections | Rint = 0.023 |
| R[F2 > 2σ(F2)] = 0.041 | 191 parameters |
| wR(F2) = 0.110 | H-atom parameters constrained |
| S = 1.09 | Δρmax = 0.16 e Å−3 |
| 2229 reflections | Δρmin = −0.17 e Å−3 |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.2735 (2) | 0.98906 (15) | 0.49784 (11) | 0.0591 (4) | |
| O2 | 0.2515 (2) | 1.39679 (17) | 0.74744 (10) | 0.0621 (4) | |
| N1 | 0.0501 (2) | 1.05193 (18) | 0.79484 (11) | 0.0462 (4) | |
| N2 | −0.0680 (3) | 0.9651 (2) | 0.75689 (14) | 0.0626 (5) | |
| N3 | −0.2433 (3) | 1.0032 (2) | 0.81950 (15) | 0.0680 (5) | |
| N4 | 0.2525 (2) | 1.16565 (17) | 0.64463 (11) | 0.0445 (4) | |
| C1 | −0.2400 (3) | 1.1155 (3) | 0.89974 (16) | 0.0547 (5) | |
| C2 | −0.3877 (3) | 1.1919 (3) | 0.9873 (2) | 0.0747 (7) | |
| H2B | −0.5150 | 1.1724 | 0.9984 | 0.090* | |
| C3 | −0.3374 (4) | 1.2959 (3) | 1.0557 (2) | 0.0806 (8) | |
| H3B | −0.4333 | 1.3491 | 1.1145 | 0.097* | |
| C4 | −0.1461 (4) | 1.3255 (3) | 1.04057 (17) | 0.0696 (6) | |
| H4A | −0.1176 | 1.3961 | 1.0902 | 0.083* | |
| C5 | −0.0002 (3) | 1.2536 (2) | 0.95475 (15) | 0.0528 (5) | |
| H5A | 0.1265 | 1.2742 | 0.9437 | 0.063* | |
| C6 | −0.0523 (3) | 1.1476 (2) | 0.88493 (14) | 0.0429 (4) | |
| C7 | 0.2508 (3) | 1.0372 (2) | 0.73567 (15) | 0.0502 (5) | |
| H7A | 0.3062 | 0.9215 | 0.7056 | 0.060* | |
| H7B | 0.3375 | 1.0507 | 0.7884 | 0.060* | |
| C8 | 0.2638 (2) | 1.1293 (2) | 0.53142 (14) | 0.0431 (4) | |
| C9 | 0.2639 (2) | 1.2957 (2) | 0.46837 (14) | 0.0402 (4) | |
| C10 | 0.2701 (3) | 1.3351 (2) | 0.35476 (14) | 0.0486 (5) | |
| H10A | 0.2770 | 1.2515 | 0.3035 | 0.058* | |
| C11 | 0.2658 (3) | 1.5050 (2) | 0.32021 (15) | 0.0526 (5) | |
| H11A | 0.2706 | 1.5361 | 0.2440 | 0.063* | |
| C12 | 0.2547 (3) | 1.6289 (2) | 0.39629 (16) | 0.0518 (5) | |
| H12A | 0.2528 | 1.7416 | 0.3703 | 0.062* | |
| C13 | 0.2461 (3) | 1.5891 (2) | 0.51025 (16) | 0.0496 (5) | |
| H13A | 0.2360 | 1.6732 | 0.5618 | 0.060* | |
| C14 | 0.2534 (2) | 1.4194 (2) | 0.54433 (13) | 0.0407 (4) | |
| C15 | 0.2517 (2) | 1.3373 (2) | 0.65864 (15) | 0.0436 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0823 (9) | 0.0380 (8) | 0.0593 (8) | −0.0198 (7) | −0.0060 (7) | −0.0107 (6) |
| O2 | 0.0844 (10) | 0.0616 (9) | 0.0486 (8) | −0.0343 (7) | −0.0012 (7) | −0.0140 (7) |
| N1 | 0.0559 (9) | 0.0451 (9) | 0.0434 (8) | −0.0227 (7) | −0.0100 (7) | 0.0027 (7) |
| N2 | 0.0816 (12) | 0.0697 (11) | 0.0536 (10) | −0.0451 (10) | −0.0189 (9) | 0.0052 (8) |
| N3 | 0.0719 (12) | 0.0840 (13) | 0.0634 (11) | −0.0445 (10) | −0.0191 (9) | 0.0122 (10) |
| N4 | 0.0525 (9) | 0.0381 (8) | 0.0426 (8) | −0.0151 (7) | −0.0009 (6) | −0.0019 (6) |
| C1 | 0.0514 (11) | 0.0585 (12) | 0.0545 (11) | −0.0193 (9) | −0.0101 (9) | 0.0187 (10) |
| C2 | 0.0557 (13) | 0.0744 (16) | 0.0823 (16) | −0.0124 (12) | 0.0023 (11) | 0.0249 (13) |
| C3 | 0.0859 (17) | 0.0606 (15) | 0.0698 (15) | −0.0006 (12) | 0.0246 (13) | 0.0083 (12) |
| C4 | 0.1028 (18) | 0.0470 (12) | 0.0529 (12) | −0.0193 (11) | 0.0055 (12) | −0.0028 (9) |
| C5 | 0.0687 (12) | 0.0429 (11) | 0.0485 (10) | −0.0211 (9) | −0.0042 (9) | 0.0018 (8) |
| C6 | 0.0503 (10) | 0.0377 (9) | 0.0407 (9) | −0.0136 (8) | −0.0085 (8) | 0.0088 (8) |
| C7 | 0.0539 (11) | 0.0445 (10) | 0.0498 (10) | −0.0118 (9) | −0.0045 (8) | 0.0009 (8) |
| C8 | 0.0411 (10) | 0.0404 (10) | 0.0469 (10) | −0.0112 (8) | −0.0003 (7) | −0.0075 (8) |
| C9 | 0.0354 (9) | 0.0382 (9) | 0.0455 (10) | −0.0104 (7) | 0.0005 (7) | −0.0040 (7) |
| C10 | 0.0478 (10) | 0.0486 (11) | 0.0462 (10) | −0.0108 (8) | 0.0009 (8) | −0.0072 (8) |
| C11 | 0.0465 (10) | 0.0565 (12) | 0.0495 (11) | −0.0114 (9) | 0.0007 (8) | 0.0062 (9) |
| C12 | 0.0449 (10) | 0.0413 (11) | 0.0655 (13) | −0.0123 (8) | 0.0005 (9) | 0.0055 (9) |
| C13 | 0.0461 (10) | 0.0405 (10) | 0.0631 (12) | −0.0165 (8) | 0.0015 (8) | −0.0075 (8) |
| C14 | 0.0357 (9) | 0.0377 (9) | 0.0483 (10) | −0.0123 (7) | 0.0011 (7) | −0.0053 (8) |
| C15 | 0.0420 (10) | 0.0430 (10) | 0.0477 (10) | −0.0164 (8) | 0.0008 (8) | −0.0088 (8) |
| O1—C8 | 1.2013 (19) | C4—H4A | 0.9300 |
| O2—C15 | 1.201 (2) | C5—C6 | 1.390 (2) |
| N1—C6 | 1.359 (2) | C5—H5A | 0.9300 |
| N1—N2 | 1.361 (2) | C7—H7A | 0.9700 |
| N1—C7 | 1.443 (2) | C7—H7B | 0.9700 |
| N2—N3 | 1.299 (2) | C8—C9 | 1.483 (2) |
| N3—C1 | 1.375 (3) | C9—C10 | 1.377 (2) |
| N4—C15 | 1.395 (2) | C9—C14 | 1.377 (2) |
| N4—C8 | 1.400 (2) | C10—C11 | 1.385 (2) |
| N4—C7 | 1.446 (2) | C10—H10A | 0.9300 |
| C1—C6 | 1.383 (2) | C11—C12 | 1.377 (3) |
| C1—C2 | 1.395 (3) | C11—H11A | 0.9300 |
| C2—C3 | 1.360 (3) | C12—C13 | 1.380 (3) |
| C2—H2B | 0.9300 | C12—H12A | 0.9300 |
| C3—C4 | 1.398 (3) | C13—C14 | 1.378 (2) |
| C3—H3B | 0.9300 | C13—H13A | 0.9300 |
| C4—C5 | 1.365 (3) | C14—C15 | 1.479 (2) |
| C6—N1—N2 | 110.53 (15) | N4—C7—H7A | 109.0 |
| C6—N1—C7 | 130.37 (15) | N1—C7—H7B | 109.0 |
| N2—N1—C7 | 119.04 (15) | N4—C7—H7B | 109.0 |
| N3—N2—N1 | 108.31 (16) | H7A—C7—H7B | 107.8 |
| N2—N3—C1 | 108.26 (16) | O1—C8—N4 | 124.63 (16) |
| C15—N4—C8 | 112.24 (14) | O1—C8—C9 | 130.09 (16) |
| C15—N4—C7 | 124.16 (15) | N4—C8—C9 | 105.28 (14) |
| C8—N4—C7 | 123.55 (14) | C10—C9—C14 | 121.57 (16) |
| N3—C1—C6 | 109.09 (17) | C10—C9—C8 | 130.10 (16) |
| N3—C1—C2 | 130.8 (2) | C14—C9—C8 | 108.33 (14) |
| C6—C1—C2 | 120.1 (2) | C9—C10—C11 | 116.98 (17) |
| C3—C2—C1 | 117.1 (2) | C9—C10—H10A | 121.5 |
| C3—C2—H2B | 121.4 | C11—C10—H10A | 121.5 |
| C1—C2—H2B | 121.4 | C12—C11—C10 | 121.42 (17) |
| C2—C3—C4 | 122.1 (2) | C12—C11—H11A | 119.3 |
| C2—C3—H3B | 118.9 | C10—C11—H11A | 119.3 |
| C4—C3—H3B | 118.9 | C11—C12—C13 | 121.36 (17) |
| C5—C4—C3 | 121.7 (2) | C11—C12—H12A | 119.3 |
| C5—C4—H4A | 119.2 | C13—C12—H12A | 119.3 |
| C3—C4—H4A | 119.2 | C14—C13—C12 | 117.14 (17) |
| C4—C5—C6 | 116.0 (2) | C14—C13—H13A | 121.4 |
| C4—C5—H5A | 122.0 | C12—C13—H13A | 121.4 |
| C6—C5—H5A | 122.0 | C9—C14—C13 | 121.52 (16) |
| N1—C6—C1 | 103.80 (16) | C9—C14—C15 | 108.84 (15) |
| N1—C6—C5 | 133.27 (17) | C13—C14—C15 | 129.64 (16) |
| C1—C6—C5 | 122.91 (17) | O2—C15—N4 | 124.42 (16) |
| N1—C7—N4 | 112.73 (14) | O2—C15—C14 | 130.33 (16) |
| N1—C7—H7A | 109.0 | N4—C15—C14 | 105.24 (14) |
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1H-Benzotriazole and its derivatives exhibit a broad spectrum of pharmacological activities, such as antifungal, antitumor and antineoplastic activities (Chen & Wu, 2005; Jiao et al., 2005). We report here the synthesis and structure of the title compound, (I), as part of our ongoing studies on new benzotriazole compounds with higher bioactivity.
In the molecular structure of (I), bond lengths and angles are within normal ranges (Fig. 1). The dihedral angle formed by the ring 1 (N1/N2/N3/C1/C6) and the ring 3 (C1/C2/C3/C4/C5/C6) is 1.4 (1)°. The dihedral angles formed by the rings 1 and 4 (C9/C10/C11/C12/C13/C14) with the ring 2 (N4/C8/C9/C14/C15) are 69.7 (3) and 1.0 (8)°, respectively. In the phthalimide group, the C?O bond lengths are 1.201 (2) and 1.2013 (19) Å, and the C—N bond lengths are 1.400 (2) and 1.395 (2) Å. There is a C—H···O intramolecular interaction (Table 2) stabilizing the observed molecular conformation.