(1H-1,2,3-Benzotriazol-1-yl)methyl benzoate.

In the title compound, C(14)H(11)N(3)O(2), the dihedral angle between the phenyl ring and the benzotriazole ring system is 76.80 (19)° and the mol-ecule has an L-shaped conformation. In the crystal, weak aromatic π-π stacking is observed, the closest centroid-centroid distance being 3.754 (2) Å.

Related literature

For related structures and the synthesis, see: Xu & Shen (2012) ▶; Zeng & Jian (2009 ▶). For applications of benzotriazole derivatives, see: Wan & Lv (2010 ▶).

Experimental

Crystal data

C14H11N3O2

M = 253.26

Monoclinic,

a = 10.7181 (4) Å

b = 6.4826 (2) Å

c = 18.7076 (7) Å

β = 96.773 (3)°

V = 1290.75 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.982, T max = 0.984

9412 measured reflections

2268 independent reflections

1352 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.162

S = 1.06

2268 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015140/hb6707sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015140/hb6707Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015140/hb6707Isup3.cml

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

C14H11N3O2	F(000) = 528
Mr = 253.26	Dx = 1.303 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1419 reflections
a = 10.7181 (4) Å	θ = 2.7–21.6°
b = 6.4826 (2) Å	µ = 0.09 mm−1
c = 18.7076 (7) Å	T = 296 K
β = 96.773 (3)°	Block, colorless
V = 1290.75 (8) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	2268 independent reflections
Radiation source: fine-focus sealed tube	1352 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.2°
phi and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −7→7
Tmin = 0.982, Tmax = 0.984	l = −22→22
9412 measured reflections

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0479P)2 + 0.4539P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2268 reflections	Δρmax = 0.14 e Å−3
181 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (18)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.7169 (3)	0.5849 (5)	0.27655 (16)	0.0599 (8)
C2	0.8234 (3)	0.7177 (6)	0.30445 (18)	0.0672 (9)
C3	0.9100 (4)	0.6382 (8)	0.3586 (2)	0.1029 (14)
H3	0.8998	0.5062	0.3765	0.123*
C4	1.0110 (5)	0.7578 (13)	0.3853 (3)	0.145 (2)
H4	1.0696	0.7062	0.4215	0.174*
C5	1.0258 (6)	0.9545 (14)	0.3586 (4)	0.157 (3)
H5	1.0944	1.0342	0.3769	0.189*
C6	0.9397 (5)	1.0320 (8)	0.3054 (3)	0.1179 (18)
H6	0.9497	1.1645	0.2878	0.141*
C7	0.8391 (3)	0.9146 (6)	0.2781 (2)	0.0814 (11)
H7	0.7810	0.9671	0.2418	0.098*
C8	0.5351 (3)	0.5700 (6)	0.19118 (18)	0.0614 (9)
C9	0.6278 (3)	0.2459 (5)	0.05103 (16)	0.0564 (8)
C10	0.6200 (3)	0.4440 (4)	0.07805 (14)	0.0505 (7)
C11	0.6600 (3)	0.6164 (5)	0.04401 (16)	0.0608 (9)
H11	0.6543	0.7485	0.0628	0.073*
C12	0.7088 (3)	0.5800 (5)	−0.01930 (17)	0.0726 (10)
H12	0.7380	0.6911	−0.0441	0.087*
C13	0.7165 (3)	0.3815 (6)	−0.04810 (17)	0.0724 (10)
H13	0.7504	0.3649	−0.0913	0.087*
C14	0.6758 (3)	0.2130 (5)	−0.01465 (17)	0.0686 (9)
H14	0.6796	0.0817	−0.0343	0.082*
H1M	0.482 (3)	0.679 (5)	0.1671 (18)	0.078 (11)*
H2M	0.491 (3)	0.493 (5)	0.2271 (18)	0.087 (11)*
N1	0.5679 (2)	0.4166 (4)	0.14069 (12)	0.0571 (7)
N2	0.5446 (3)	0.2141 (4)	0.15102 (14)	0.0729 (8)
N3	0.5796 (3)	0.1092 (4)	0.09718 (15)	0.0752 (9)
O1	0.64454 (19)	0.6783 (3)	0.22152 (10)	0.0584 (6)
O2	0.6951 (2)	0.4154 (4)	0.29774 (13)	0.0830 (8)

	U11	U22	U33	U12	U13	U23
C1	0.065 (2)	0.067 (2)	0.0494 (17)	0.0088 (18)	0.0141 (16)	0.0005 (16)
C2	0.055 (2)	0.090 (3)	0.057 (2)	−0.0006 (19)	0.0115 (17)	−0.0160 (19)
C3	0.071 (3)	0.155 (4)	0.080 (3)	0.016 (3)	−0.003 (2)	−0.014 (3)
C4	0.075 (4)	0.240 (8)	0.114 (5)	0.002 (5)	−0.015 (3)	−0.043 (5)
C5	0.075 (4)	0.228 (8)	0.170 (7)	−0.039 (5)	0.018 (4)	−0.089 (7)
C6	0.085 (3)	0.125 (4)	0.152 (5)	−0.041 (3)	0.050 (3)	−0.057 (4)
C7	0.072 (3)	0.089 (3)	0.088 (3)	−0.018 (2)	0.030 (2)	−0.026 (2)
C8	0.061 (2)	0.070 (2)	0.0534 (19)	0.0043 (19)	0.0083 (18)	−0.0129 (18)
C9	0.064 (2)	0.0560 (17)	0.0497 (17)	0.0003 (15)	0.0079 (16)	−0.0034 (14)
C10	0.0551 (19)	0.0539 (17)	0.0423 (15)	0.0009 (14)	0.0045 (14)	−0.0016 (13)
C11	0.076 (2)	0.0547 (18)	0.0516 (17)	−0.0021 (16)	0.0078 (17)	−0.0012 (14)
C12	0.085 (3)	0.079 (2)	0.0553 (19)	−0.0057 (19)	0.0155 (19)	0.0080 (18)
C13	0.081 (3)	0.092 (3)	0.0465 (18)	0.006 (2)	0.0182 (17)	−0.0043 (18)
C14	0.081 (2)	0.070 (2)	0.0552 (19)	0.0090 (18)	0.0105 (18)	−0.0145 (17)
N1	0.0712 (18)	0.0564 (15)	0.0454 (13)	0.0007 (13)	0.0136 (13)	−0.0026 (12)
N2	0.103 (2)	0.0594 (17)	0.0583 (17)	−0.0114 (15)	0.0191 (16)	−0.0007 (14)
N3	0.110 (2)	0.0569 (16)	0.0611 (17)	−0.0071 (15)	0.0225 (17)	−0.0055 (14)
O1	0.0718 (15)	0.0583 (12)	0.0450 (11)	−0.0001 (11)	0.0064 (11)	−0.0033 (10)
O2	0.0905 (19)	0.0774 (16)	0.0804 (17)	0.0015 (13)	0.0077 (14)	0.0232 (13)

C1—O2	1.200 (3)	C8—H1M	0.98 (3)
C1—O1	1.356 (3)	C8—H2M	1.00 (3)
C1—C2	1.476 (5)	C9—N3	1.379 (4)
C2—C7	1.385 (5)	C9—C10	1.386 (4)
C2—C3	1.389 (5)	C9—C14	1.404 (4)
C3—C4	1.377 (7)	C10—N1	1.367 (3)
C3—H3	0.9300	C10—C11	1.380 (4)
C4—C5	1.385 (9)	C11—C12	1.371 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.371 (8)	C12—C13	1.401 (4)
C5—H5	0.9300	C12—H12	0.9300
C6—C7	1.369 (6)	C13—C14	1.357 (4)
C6—H6	0.9300	C13—H13	0.9300
C7—H7	0.9300	C14—H14	0.9300
C8—O1	1.426 (4)	N1—N2	1.355 (3)
C8—N1	1.443 (4)	N2—N3	1.306 (3)
O2—C1—O1	122.9 (3)	H1M—C8—H2M	112 (3)
O2—C1—C2	126.1 (3)	N3—C9—C10	108.9 (3)
O1—C1—C2	111.0 (3)	N3—C9—C14	130.8 (3)
C7—C2—C3	120.2 (4)	C10—C9—C14	120.3 (3)
C7—C2—C1	122.2 (3)	N1—C10—C11	133.0 (3)
C3—C2—C1	117.6 (4)	N1—C10—C9	103.9 (2)
C4—C3—C2	119.0 (5)	C11—C10—C9	123.1 (3)
C4—C3—H3	120.5	C12—C11—C10	115.5 (3)
C2—C3—H3	120.5	C12—C11—H11	122.3
C3—C4—C5	120.4 (7)	C10—C11—H11	122.3
C3—C4—H4	119.8	C11—C12—C13	122.4 (3)
C5—C4—H4	119.8	C11—C12—H12	118.8
C6—C5—C4	120.2 (7)	C13—C12—H12	118.8
C6—C5—H5	119.9	C14—C13—C12	121.7 (3)
C4—C5—H5	119.9	C14—C13—H13	119.1
C7—C6—C5	120.0 (6)	C12—C13—H13	119.1
C7—C6—H6	120.0	C13—C14—C9	116.9 (3)
C5—C6—H6	120.0	C13—C14—H14	121.6
C6—C7—C2	120.2 (5)	C9—C14—H14	121.6
C6—C7—H7	119.9	N2—N1—C10	110.4 (2)
C2—C7—H7	119.9	N2—N1—C8	120.7 (3)
O1—C8—N1	110.3 (3)	C10—N1—C8	128.8 (3)
O1—C8—H1M	103.6 (18)	N3—N2—N1	108.6 (2)
N1—C8—H1M	111.5 (19)	N2—N3—C9	108.1 (2)
O1—C8—H2M	114.3 (19)	C1—O1—C8	116.9 (3)
N1—C8—H2M	105.7 (19)
O2—C1—C2—C7	−177.9 (3)	C11—C12—C13—C14	−0.1 (6)
O1—C1—C2—C7	3.0 (4)	C12—C13—C14—C9	−1.2 (5)
O2—C1—C2—C3	2.5 (5)	N3—C9—C14—C13	179.8 (3)
O1—C1—C2—C3	−176.6 (3)	C10—C9—C14—C13	1.9 (5)
C7—C2—C3—C4	−0.1 (6)	C11—C10—N1—N2	−180.0 (3)
C1—C2—C3—C4	179.5 (4)	C9—C10—N1—N2	−0.4 (3)
C2—C3—C4—C5	0.1 (8)	C11—C10—N1—C8	1.9 (6)
C3—C4—C5—C6	0.1 (10)	C9—C10—N1—C8	−178.5 (3)
C4—C5—C6—C7	−0.4 (9)	O1—C8—N1—N2	119.7 (3)
C5—C6—C7—C2	0.4 (6)	O1—C8—N1—C10	−62.3 (4)
C3—C2—C7—C6	−0.1 (5)	C10—N1—N2—N3	−0.1 (4)
C1—C2—C7—C6	−179.7 (3)	C8—N1—N2—N3	178.3 (3)
N3—C9—C10—N1	0.7 (3)	N1—N2—N3—C9	0.5 (4)
C14—C9—C10—N1	179.0 (3)	C10—C9—N3—N2	−0.8 (4)
N3—C9—C10—C11	−179.7 (3)	C14—C9—N3—N2	−178.9 (3)
C14—C9—C10—C11	−1.3 (5)	O2—C1—O1—C8	3.2 (4)
N1—C10—C11—C12	179.6 (3)	C2—C1—O1—C8	−177.7 (2)
C9—C10—C11—C12	0.0 (5)	N1—C8—O1—C1	−81.1 (3)
C10—C11—C12—C13	0.7 (5)