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 ▶); Jiao et al. (2005 ▶).

Experimental

Crystal data

• C₁₅H₁₀N₄O₂

• M _r = 278.27

• Triclinic,

• 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) ų

• 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

• Δρ_max = 0.16 e Å⁻³

• Δρ_min = −0.17 e Å⁻³

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.

Supplementary Material

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

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

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 U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

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

Crystal data

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

Data collection

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

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

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

	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)

Atomic displacement parameters (Ų)

	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, °)

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, °)

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