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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1782.
Published online 2008 August 20. doi:  10.1107/S160053680802610X
PMCID: PMC2960721

N-(1H-1,2,3-Benzotriazol-1-ylmeth­yl)phthalimide

Abstract

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.

Related literature

For related literature, see: Chen & Wu (2005 [triangle]); Jiao et al. (2005 [triangle]).

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Object name is e-64-o1782-scheme1.jpg

Experimental

Crystal data

  • C15H10N4O2
  • M r = 278.27
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1782-efi1.jpg
  • a = 6.9481 (11) Å
  • b = 8.0041 (13) Å
  • c = 12.030 (2) Å
  • α = 85.715 (3)°
  • β = 81.283 (3)°
  • γ = 73.398 (3)°
  • V = 633.38 (18) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 (2) K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 3364 measured reflections
  • 2229 independent reflections
  • 1689 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.110
  • S = 1.08
  • 2229 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802610X/bh2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802610X/bh2185Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

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).

Figures

Fig. 1.
The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C15H10N4O2Z = 2
Mr = 278.27F000 = 288
Triclinic, P1Dx = 1.459 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 6.9481 (11) ÅCell parameters from 1689 reflections
b = 8.0041 (13) Åθ = 1.7–28.2º
c = 12.030 (2) ŵ = 0.10 mm1
α = 85.715 (3)ºT = 293 (2) K
β = 81.283 (3)ºBlock, colourless
γ = 73.398 (3)º0.25 × 0.20 × 0.18 mm
V = 633.38 (18) Å3

Data collection

Bruker SMART CCD area-detector diffractometer1689 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Monochromator: graphiteθmax = 25.0º
T = 293(2) Kθmin = 1.7º
[var phi] and ω scansh = −7→8
Absorption correction: nonek = −5→9
3364 measured reflectionsl = −14→14
2229 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.09Δρmax = 0.16 e Å3
2229 reflectionsΔρmin = −0.17 e Å3
191 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.069 (7)
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.2735 (2)0.98906 (15)0.49784 (11)0.0591 (4)
O20.2515 (2)1.39679 (17)0.74744 (10)0.0621 (4)
N10.0501 (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)
N40.2525 (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−0.51501.17240.99840.090*
C3−0.3374 (4)1.2959 (3)1.0557 (2)0.0806 (8)
H3B−0.43331.34911.11450.097*
C4−0.1461 (4)1.3255 (3)1.04057 (17)0.0696 (6)
H4A−0.11761.39611.09020.083*
C5−0.0002 (3)1.2536 (2)0.95475 (15)0.0528 (5)
H5A0.12651.27420.94370.063*
C6−0.0523 (3)1.1476 (2)0.88493 (14)0.0429 (4)
C70.2508 (3)1.0372 (2)0.73567 (15)0.0502 (5)
H7A0.30620.92150.70560.060*
H7B0.33751.05070.78840.060*
C80.2638 (2)1.1293 (2)0.53142 (14)0.0431 (4)
C90.2639 (2)1.2957 (2)0.46837 (14)0.0402 (4)
C100.2701 (3)1.3351 (2)0.35476 (14)0.0486 (5)
H10A0.27701.25150.30350.058*
C110.2658 (3)1.5050 (2)0.32021 (15)0.0526 (5)
H11A0.27061.53610.24400.063*
C120.2547 (3)1.6289 (2)0.39629 (16)0.0518 (5)
H12A0.25281.74160.37030.062*
C130.2461 (3)1.5891 (2)0.51025 (16)0.0496 (5)
H13A0.23601.67320.56180.060*
C140.2534 (2)1.4194 (2)0.54433 (13)0.0407 (4)
C150.2517 (2)1.3373 (2)0.65864 (15)0.0436 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0823 (9)0.0380 (8)0.0593 (8)−0.0198 (7)−0.0060 (7)−0.0107 (6)
O20.0844 (10)0.0616 (9)0.0486 (8)−0.0343 (7)−0.0012 (7)−0.0140 (7)
N10.0559 (9)0.0451 (9)0.0434 (8)−0.0227 (7)−0.0100 (7)0.0027 (7)
N20.0816 (12)0.0697 (11)0.0536 (10)−0.0451 (10)−0.0189 (9)0.0052 (8)
N30.0719 (12)0.0840 (13)0.0634 (11)−0.0445 (10)−0.0191 (9)0.0122 (10)
N40.0525 (9)0.0381 (8)0.0426 (8)−0.0151 (7)−0.0009 (6)−0.0019 (6)
C10.0514 (11)0.0585 (12)0.0545 (11)−0.0193 (9)−0.0101 (9)0.0187 (10)
C20.0557 (13)0.0744 (16)0.0823 (16)−0.0124 (12)0.0023 (11)0.0249 (13)
C30.0859 (17)0.0606 (15)0.0698 (15)−0.0006 (12)0.0246 (13)0.0083 (12)
C40.1028 (18)0.0470 (12)0.0529 (12)−0.0193 (11)0.0055 (12)−0.0028 (9)
C50.0687 (12)0.0429 (11)0.0485 (10)−0.0211 (9)−0.0042 (9)0.0018 (8)
C60.0503 (10)0.0377 (9)0.0407 (9)−0.0136 (8)−0.0085 (8)0.0088 (8)
C70.0539 (11)0.0445 (10)0.0498 (10)−0.0118 (9)−0.0045 (8)0.0009 (8)
C80.0411 (10)0.0404 (10)0.0469 (10)−0.0112 (8)−0.0003 (7)−0.0075 (8)
C90.0354 (9)0.0382 (9)0.0455 (10)−0.0104 (7)0.0005 (7)−0.0040 (7)
C100.0478 (10)0.0486 (11)0.0462 (10)−0.0108 (8)0.0009 (8)−0.0072 (8)
C110.0465 (10)0.0565 (12)0.0495 (11)−0.0114 (9)0.0007 (8)0.0062 (9)
C120.0449 (10)0.0413 (11)0.0655 (13)−0.0123 (8)0.0005 (9)0.0055 (9)
C130.0461 (10)0.0405 (10)0.0631 (12)−0.0165 (8)0.0015 (8)−0.0075 (8)
C140.0357 (9)0.0377 (9)0.0483 (10)−0.0123 (7)0.0011 (7)−0.0053 (8)
C150.0420 (10)0.0430 (10)0.0477 (10)−0.0164 (8)0.0008 (8)−0.0088 (8)

Geometric parameters (Å, °)

O1—C81.2013 (19)C4—H4A0.9300
O2—C151.201 (2)C5—C61.390 (2)
N1—C61.359 (2)C5—H5A0.9300
N1—N21.361 (2)C7—H7A0.9700
N1—C71.443 (2)C7—H7B0.9700
N2—N31.299 (2)C8—C91.483 (2)
N3—C11.375 (3)C9—C101.377 (2)
N4—C151.395 (2)C9—C141.377 (2)
N4—C81.400 (2)C10—C111.385 (2)
N4—C71.446 (2)C10—H10A0.9300
C1—C61.383 (2)C11—C121.377 (3)
C1—C21.395 (3)C11—H11A0.9300
C2—C31.360 (3)C12—C131.380 (3)
C2—H2B0.9300C12—H12A0.9300
C3—C41.398 (3)C13—C141.378 (2)
C3—H3B0.9300C13—H13A0.9300
C4—C51.365 (3)C14—C151.479 (2)
C6—N1—N2110.53 (15)N4—C7—H7A109.0
C6—N1—C7130.37 (15)N1—C7—H7B109.0
N2—N1—C7119.04 (15)N4—C7—H7B109.0
N3—N2—N1108.31 (16)H7A—C7—H7B107.8
N2—N3—C1108.26 (16)O1—C8—N4124.63 (16)
C15—N4—C8112.24 (14)O1—C8—C9130.09 (16)
C15—N4—C7124.16 (15)N4—C8—C9105.28 (14)
C8—N4—C7123.55 (14)C10—C9—C14121.57 (16)
N3—C1—C6109.09 (17)C10—C9—C8130.10 (16)
N3—C1—C2130.8 (2)C14—C9—C8108.33 (14)
C6—C1—C2120.1 (2)C9—C10—C11116.98 (17)
C3—C2—C1117.1 (2)C9—C10—H10A121.5
C3—C2—H2B121.4C11—C10—H10A121.5
C1—C2—H2B121.4C12—C11—C10121.42 (17)
C2—C3—C4122.1 (2)C12—C11—H11A119.3
C2—C3—H3B118.9C10—C11—H11A119.3
C4—C3—H3B118.9C11—C12—C13121.36 (17)
C5—C4—C3121.7 (2)C11—C12—H12A119.3
C5—C4—H4A119.2C13—C12—H12A119.3
C3—C4—H4A119.2C14—C13—C12117.14 (17)
C4—C5—C6116.0 (2)C14—C13—H13A121.4
C4—C5—H5A122.0C12—C13—H13A121.4
C6—C5—H5A122.0C9—C14—C13121.52 (16)
N1—C6—C1103.80 (16)C9—C14—C15108.84 (15)
N1—C6—C5133.27 (17)C13—C14—C15129.64 (16)
C1—C6—C5122.91 (17)O2—C15—N4124.42 (16)
N1—C7—N4112.73 (14)O2—C15—C14130.33 (16)
N1—C7—H7A109.0N4—C15—C14105.24 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7A···O10.972.552.890 (2)101

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2185).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett.7, 475–477. [PubMed]
  • Jiao, K., Wang, Q. X., Sun, W. & Jian, F. F. (2005). J. Inorg. Biochem.99, 1369–1375. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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