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

Wang, S.-Q.; Jian, F.-F.; Liu, H.-Q.

doi:10.1107/S160053680802610X

organic compounds

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Volume 64| Part 9| September 2008| Page o1782

doi:10.1107/S160053680802610X

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

Su-Qing Wang,^a Fang-Fang Jian ^a ^* and Huan-Qiang Liu ^b

^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 ); Jiao et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₀N₄O₂
M_r = 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)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.110
S = 1.08
2229 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

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

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

checkCIF report

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.

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

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

C₁₅H₁₀N₄O₂	Z = 2
M_r = 278.27	F(000) = 288
Triclinic, P1	D_x = 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 = 1.7–28.2°
c = 12.030 (2) Å	µ = 0.10 mm⁻¹
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 tube	R_int = 0.023
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ϕ and ω scans	h = −7→8
3364 measured reflections	k = −5→9
2229 independent reflections	l = −14→14

Refinement top

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0531P)² + 0.0288P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2229 reflections	Δρ_max = 0.16 e Å⁻³
191 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.069 (7)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₀N₄O₂	γ = 73.398 (3)°
M_r = 278.27	V = 633.38 (18) Å³
Triclinic, P1	Z = 2
a = 6.9481 (11) Å	Mo Kα radiation
b = 8.0041 (13) Å	µ = 0.10 mm⁻¹
c = 12.030 (2) Å	T = 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 reflections	R_int = 0.023
2229 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.09	Δρ_max = 0.16 e Å⁻³
2229 reflections	Δρ_min = −0.18 e Å⁻³
191 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀N₄O₂
M_r	278.27
Crystal system, space group	Triclinic, 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)
V (Å³)	633.38 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3364, 2229, 1689
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.09
No. of reflections	2229
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.97	2.55	2.890 (2)	100.7

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z.-Y. & Wu, M.-J. (2005). Org. Lett. 7, 475–477. Web of Science CrossRef PubMed CAS Google Scholar
Jiao, 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1782

doi:10.1107/S160053680802610X

Open

access