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

Abstract

In the title compound, C₁₄H₁₁N₃O₂, the dihedral angle between the phenyl ring and the benzotriazole ring system is 76.80 (19)° and the mol­ecule 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 _r = 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) ų

• 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

• Δρ_max = 0.14 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

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

supplementary crystallographic information

Comment

Benzotriazole derivatives have been broadly researched due to their potential applications (Wan & Lv, 2010). Herein, we have synthesized a new benzotriazole derivative(Fig. 1), C₁₂H₁₅N₃O₂. Bond lengths and angles are comparable to other reported benzotriazol-1-yl intermediate derivatives (Zeng & Jian, 2009; Xu & Shen, 2012). Furthermore, the dihedral angle between the mean planes of the phenyl and benzotriazole rings is 76.80 (19)°. In the crystal, π–π stacking is observed between the inversion related phenyl rings of benzotriazolyl, the closest centroid-centroid distance being 3.754 (2)Å.

Experimental

The title compound synthesis method is similar to that reported by Xu & Shen (2012), but methylene chloride was replaced by benzoyl chloride

Refinement

The H atoms on the CH₂ group were located by difference maps and freely refined without constraints. H atoms bonded to the remaining C atoms were included in calculated positions and treated as riding with C–H =0.93Å and U_iso(H)=1.2Ueq(aromatic C).

Figures

Fig. 1.

The molecular structure of the title compound with 50% probability displacement ellipsoids.

Crystal data

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

Data collection

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

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)

Special details

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.

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

	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)

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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)