N-(1H-1,2,3-Benzotriazol-1-ylmeth-yl)phthalimide.

THE TITLE COMPOUND [SYSTEMATIC NAME: 2-(1H-1,2,3-benzotriazol-1-ylmeth-yl)isoindole-1,3-dione], C(15)H(10)N(4)O(2), was prepared by the reaction of 1H-benzotriazole and 2-bromo-methyl-isoindole-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 intra-molecular hydrogen bond involving a carbonyl O atom as acceptor stabilizes the observed mol-ecular conformation.

Related literature

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

Experimental

Crystal data

C15H10N4O2

M = 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) 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 ▶); 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.

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

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

	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)

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

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