organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and bDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: ffjian2008@163.com

(Received 11 July 2008; accepted 13 August 2008; online 20 August 2008)

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[Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475-477.]); Jiao et al. (2005[Jiao, K., Wang, Q. X., Sun, W. & Jian, F. F. (2005). J. Inorg. Biochem. 99, 1369-1375.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10N4O2

  • Mr = 278.27

  • Triclinic, [P \overline 1]

  • 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)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7A⋯O1 0.97 2.55 2.890 (2) 101

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.
N-(1H-1,2,3-Benzotriazol-1-ylmethyl)phthalimide top
Crystal data top
C15H10N4O2Z = 2
Mr = 278.27F(000) = 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 = 1.7–28.2°
c = 12.030 (2) ŵ = 0.10 mm1
α = 85.715 (3)°T = 293 K
β = 81.283 (3)°Block, colourless
γ = 73.398 (3)°0.25 × 0.20 × 0.18 mm
V = 633.38 (18) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
1689 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ϕ and ω scansh = 78
3364 measured reflectionsk = 59
2229 independent reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0531P)2 + 0.0288P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2229 reflectionsΔρmax = 0.16 e Å3
191 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.069 (7)
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H10N4O2γ = 73.398 (3)°
Mr = 278.27V = 633.38 (18) Å3
Triclinic, P1Z = 2
a = 6.9481 (11) ÅMo Kα radiation
b = 8.0041 (13) ŵ = 0.10 mm1
c = 12.030 (2) ÅT = 293 K
α = 85.715 (3)°0.25 × 0.20 × 0.18 mm
β = 81.283 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1689 reflections with I > 2σ(I)
3364 measured reflectionsRint = 0.023
2229 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.09Δρmax = 0.16 e Å3
2229 reflectionsΔρmin = 0.18 e Å3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
N20.0680 (3)0.9651 (2)0.75689 (14)0.0626 (5)
N30.2433 (3)1.0032 (2)0.81950 (15)0.0680 (5)
N40.2525 (2)1.16565 (17)0.64463 (11)0.0445 (4)
C10.2400 (3)1.1155 (3)0.89974 (16)0.0547 (5)
C20.3877 (3)1.1919 (3)0.9873 (2)0.0747 (7)
H2B0.51501.17240.99840.090*
C30.3374 (4)1.2959 (3)1.0557 (2)0.0806 (8)
H3B0.43331.34911.11450.097*
C40.1461 (4)1.3255 (3)1.04057 (17)0.0696 (6)
H4A0.11761.39611.09020.083*
C50.0002 (3)1.2536 (2)0.95475 (15)0.0528 (5)
H5A0.12651.27420.94370.063*
C60.0523 (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) top
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, º) top
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, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O10.972.552.890 (2)101

Experimental details

Crystal data
Chemical formulaC15H10N4O2
Mr278.27
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.9481 (11), 8.0041 (13), 12.030 (2)
α, β, γ (°)85.715 (3), 81.283 (3), 73.398 (3)
V3)633.38 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3364, 2229, 1689
Rint0.023
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.110, 1.09
No. of reflections2229
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O10.972.552.890 (2)100.7
 

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477.  Web of Science CrossRef PubMed CAS Google Scholar
First citationJiao, K., Wang, Q. X., Sun, W. & Jian, F. F. (2005). J. Inorg. Biochem. 99, 1369–1375.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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