1-Benzyl-1H-benzotriazole

Selvarathy Grace, P.; Jebas, S.R.; Ravindran Durai Nayagam, B.; Schollmeyer, D.

doi:10.1107/S1600536812010951

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1132

doi:10.1107/S1600536812010951

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1-Benzyl-1H-benzotriazole

P. Selvarathy Grace,^a Samuel Robinson Jebas,^b B. Ravindran Durai Nayagam ^a ^* and Dieter Schollmeyer ^c

^aDepartment of Chemistry, Popes College, Sawyerpuram 628 251, Tamilnadu, India, ^bDepartment of Physics, Sethupathy Govt. Arts College, Ramanathapuram 623 502, Tamilnadu, India, and ^cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: b_ravidurai@yahoo.com

(Received 24 February 2012; accepted 13 March 2012; online 21 March 2012)

In the title compound, C₁₃H₁₁N₃, the benzotriazole ring system is essentially planar, with a maximum deviation of 0.0173 (18) Å, and forms a dihedral angle of 75.08 (8)Å with the phenyl ring. In the crystal, pairs of weak C—H⋯N hydrogen bonds form inversion dimers. In addition, there are weak C—H⋯π(arene) interactions and weak π–π stacking interactions, with a centroid–centroid distance of 3.673 (11) Å.

Related literature

For the biological activity of benzotriazole derivatives, see: Katarzyna et al. (2005 ); Sarala et al. (2007 ). For their applications, see: Kopec et al. (2008 ); Krawczyk & Gdaniec (2005 ); Smith et al. (2001 ); Sha et al. (1996 ). For a related structure, see: Ravindran et al. (2009 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₁N₃
M_r = 209.25
Monoclinic, P 2₁ /c
a = 11.5734 (10) Å
b = 5.9705 (4) Å
c = 16.1202 (14) Å
β = 106.490 (4)°
V = 1068.07 (15) Å³
Z = 4
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 193 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ; Wiehl & Schollmeyer, 1994 ) T_min = 0.832, T_max = 0.939
2125 measured reflections
2020 independent reflections
1788 reflections with I > 2σ(I)
R_int = 0.108
3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.138
S = 1.12
2020 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N1ⁱ	0.95	2.62	3.513 (3)	158
C14—H14⋯Cgⁱⁱ	0.95	2.69	3.583 (2)	157
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994); 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812010951/lh5426sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010951/lh5426Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010951/lh5426Isup3.cml

checkCIF report

Comment top

Benzotriazole derivatives show biological activities such as anti-inflammatory, diuretic, antiviral and are antihypertensive agents (Katarzyna et al., 2005; Sarala et al., 2007). They are used as corrosion inhibitors, antifreeze agents, ultraviolet light stabilizer for plastics and as antifoggants in photography (Krawczyk & Gdaniec, 2005; Smith et al., 2001). N-Aryloxy derivatives of benzotriazole have anti-mycobacterial activity (Kopec et al., 2008). Benzotriazole possessing three vicinal N atoms, is used as an antifouling and antiwear reagent (Sha et al., 1996). These applications of benzotriazole compounds prompted us to synthesize the title compound and herein we report the crystal structure.

In (I) (Fig 1), the bond lengths (Allen et al., 1987) and bond angles have normal values. The benzotriazole ring system is essentially planar with a maximum deviation of 0.0173 (18) Å for atom N3. The mean plane of the benzotriazole ring system (N1—N3/C4—C9) forms a dihedral angle of 75.08 (8) Å with the mean plane of the phenyl ring (C11—C16).

In the crystal, pairs of weak C—H···N hydrogen bonds form centrosymmetric dimers (Fig. 2). In addition, there are weak π–π stacking interactions between ring N1-N3/C4/C9 and ring C4—C9(1-x, 1-y, 1-z) with a centroid-centroid distance of 3.673 (11)Å.

Related literature top

For the biological activity of benzotriazole derivatives, see: Katarzyna et al. (2005); Sarala et al. (2007). For their applications, see: Kopec et al. (2008); Krawczyk & Gdaniec (2005); Smith et al. (2001); Sha et al. (1996). For a related structure, see: Ravindran et al. (2009). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of the sodium salt of benzotriazole (0.148 g, 1 mmol) benzyl chloride (0.126 g, 1 mmol) in ethanol and water (5 ml) were heated at 333K with continous stirring for 4 h. The mixture was kept aside for slow evaporation. After two weeks crystals of (I) suitable for X-ray diffraction were formed.

Structure description top

For the biological activity of benzotriazole derivatives, see: Katarzyna et al. (2005); Sarala et al. (2007). For their applications, see: Kopec et al. (2008); Krawczyk & Gdaniec (2005); Smith et al. (2001); Sha et al. (1996). For a related structure, see: Ravindran et al. (2009). For standard bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994); 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: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

1-Benzyl-1H-benzotriazole top

Crystal data top

C₁₃H₁₁N₃	F(000) = 440
M_r = 209.25	D_x = 1.301 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.5734 (10) Å	θ = 55–68°
b = 5.9705 (4) Å	µ = 0.64 mm⁻¹
c = 16.1202 (14) Å	T = 193 K
β = 106.490 (4)°	Block, colourless
V = 1068.07 (15) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1788 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.108
Graphite monochromator	θ_max = 70.0°, θ_min = 4.0°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994)	k = 0→7
T_min = 0.832, T_max = 0.939	l = −19→18
2125 measured reflections	3 standard reflections every 60 min
2020 independent reflections	intensity decay: 2%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0628P)² + 0.3976P] where P = (F_o² + 2F_c²)/3
2020 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₃H₁₁N₃	V = 1068.07 (15) Å³
M_r = 209.25	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.5734 (10) Å	µ = 0.64 mm⁻¹
b = 5.9705 (4) Å	T = 193 K
c = 16.1202 (14) Å	0.30 × 0.20 × 0.10 mm
β = 106.490 (4)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1788 reflections with I > 2σ(I)
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994)	R_int = 0.108
T_min = 0.832, T_max = 0.939	3 standard reflections every 60 min
2125 measured reflections	intensity decay: 2%
2020 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.12	Δρ_max = 0.30 e Å⁻³
2020 reflections	Δρ_min = −0.30 e Å⁻³
145 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.42315 (15)	0.1763 (3)	0.37392 (11)	0.0331 (4)
N2	0.40768 (14)	0.2958 (3)	0.30376 (10)	0.0312 (4)
N3	0.35886 (13)	0.4957 (3)	0.31508 (10)	0.0255 (4)
C4	0.34149 (14)	0.5049 (3)	0.39488 (11)	0.0232 (4)
C5	0.29338 (17)	0.6694 (3)	0.43720 (12)	0.0291 (4)
H5	0.2638	0.8079	0.4105	0.035*
C6	0.29158 (18)	0.6177 (4)	0.52002 (13)	0.0345 (5)
H6	0.2588	0.7231	0.5513	0.041*
C7	0.33691 (17)	0.4130 (4)	0.55981 (12)	0.0332 (5)
H7	0.3349	0.3858	0.6174	0.040*
C8	0.38387 (17)	0.2517 (4)	0.51801 (13)	0.0324 (5)
H8	0.4147	0.1145	0.5453	0.039*
C9	0.38385 (15)	0.3007 (3)	0.43252 (12)	0.0256 (4)
C10	0.33293 (16)	0.6650 (3)	0.24689 (12)	0.0300 (4)
H10A	0.3745	0.6244	0.2031	0.036*
H10B	0.3648	0.8114	0.2721	0.036*
C11	0.19948 (16)	0.6862 (3)	0.20336 (11)	0.0254 (4)
C12	0.13833 (19)	0.8816 (3)	0.21182 (13)	0.0343 (5)
H12	0.1804	1.0015	0.2461	0.041*
C13	0.0167 (2)	0.9019 (4)	0.17048 (15)	0.0425 (5)
H13	−0.0246	1.0354	0.1769	0.051*
C14	−0.04510 (19)	0.7302 (4)	0.12006 (15)	0.0434 (6)
H14	−0.1285	0.7459	0.0912	0.052*
C15	0.01477 (19)	0.5340 (4)	0.11147 (13)	0.0376 (5)
H15	−0.0276	0.4148	0.0769	0.045*
C16	0.13627 (17)	0.5127 (3)	0.15333 (12)	0.0310 (4)
H16	0.1769	0.3778	0.1478	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0330 (9)	0.0294 (9)	0.0363 (9)	0.0057 (7)	0.0088 (7)	−0.0014 (7)
N2	0.0301 (8)	0.0319 (9)	0.0331 (9)	0.0056 (7)	0.0113 (7)	−0.0050 (7)
N3	0.0241 (7)	0.0282 (8)	0.0260 (8)	0.0022 (6)	0.0099 (6)	−0.0012 (6)
C4	0.0192 (8)	0.0264 (9)	0.0247 (9)	−0.0029 (7)	0.0072 (6)	−0.0010 (7)
C5	0.0314 (9)	0.0262 (10)	0.0323 (10)	0.0010 (8)	0.0133 (8)	−0.0016 (8)
C6	0.0370 (10)	0.0374 (11)	0.0331 (10)	−0.0026 (9)	0.0164 (8)	−0.0062 (9)
C7	0.0329 (10)	0.0446 (12)	0.0232 (9)	−0.0092 (9)	0.0097 (7)	0.0026 (8)
C8	0.0303 (9)	0.0327 (11)	0.0322 (10)	−0.0045 (8)	0.0059 (8)	0.0069 (8)
C9	0.0213 (8)	0.0250 (9)	0.0294 (9)	−0.0012 (7)	0.0055 (7)	0.0002 (7)
C10	0.0289 (9)	0.0354 (11)	0.0288 (9)	−0.0016 (8)	0.0130 (8)	0.0051 (8)
C11	0.0285 (9)	0.0303 (10)	0.0212 (8)	0.0005 (7)	0.0129 (7)	0.0064 (7)
C12	0.0410 (11)	0.0291 (10)	0.0356 (11)	0.0025 (9)	0.0155 (9)	0.0016 (9)
C13	0.0417 (12)	0.0384 (12)	0.0501 (13)	0.0146 (10)	0.0174 (10)	0.0082 (10)
C14	0.0303 (10)	0.0581 (15)	0.0403 (12)	0.0073 (10)	0.0074 (9)	0.0125 (11)
C15	0.0372 (11)	0.0433 (12)	0.0319 (10)	−0.0057 (9)	0.0090 (8)	−0.0009 (9)
C16	0.0345 (10)	0.0298 (10)	0.0315 (10)	0.0027 (8)	0.0137 (8)	0.0010 (8)

Geometric parameters (Å, º) top

N1—N2	1.306 (2)	C10—C11	1.509 (2)
N1—C9	1.376 (2)	C10—H10A	0.9900
N2—N3	1.354 (2)	C10—H10B	0.9900
N3—C4	1.358 (2)	C11—C16	1.387 (3)
N3—C10	1.460 (2)	C11—C12	1.391 (3)
C4—C9	1.388 (3)	C12—C13	1.382 (3)
C4—C5	1.399 (3)	C12—H12	0.9500
C5—C6	1.376 (3)	C13—C14	1.376 (3)
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.411 (3)	C14—C15	1.388 (3)
C6—H6	0.9500	C14—H14	0.9500
C7—C8	1.373 (3)	C15—C16	1.382 (3)
C7—H7	0.9500	C15—H15	0.9500
C8—C9	1.409 (3)	C16—H16	0.9500
C8—H8	0.9500

N2—N1—C9	108.00 (16)	N3—C10—H10A	109.2
N1—N2—N3	108.93 (15)	C11—C10—H10A	109.2
N2—N3—C4	110.05 (15)	N3—C10—H10B	109.2
N2—N3—C10	120.85 (15)	C11—C10—H10B	109.2
C4—N3—C10	129.11 (15)	H10A—C10—H10B	107.9
N3—C4—C9	104.45 (16)	C16—C11—C12	118.97 (18)
N3—C4—C5	132.60 (17)	C16—C11—C10	120.57 (17)
C9—C4—C5	122.94 (17)	C12—C11—C10	120.46 (18)
C6—C5—C4	115.70 (18)	C13—C12—C11	120.2 (2)
C6—C5—H5	122.2	C13—C12—H12	119.9
C4—C5—H5	122.2	C11—C12—H12	119.9
C5—C6—C7	121.96 (19)	C14—C13—C12	120.5 (2)
C5—C6—H6	119.0	C14—C13—H13	119.8
C7—C6—H6	119.0	C12—C13—H13	119.8
C8—C7—C6	122.18 (18)	C13—C14—C15	119.8 (2)
C8—C7—H7	118.9	C13—C14—H14	120.1
C6—C7—H7	118.9	C15—C14—H14	120.1
C7—C8—C9	116.38 (18)	C16—C15—C14	119.8 (2)
C7—C8—H8	121.8	C16—C15—H15	120.1
C9—C8—H8	121.8	C14—C15—H15	120.1
N1—C9—C4	108.56 (16)	C15—C16—C11	120.71 (19)
N1—C9—C8	130.63 (18)	C15—C16—H16	119.6
C4—C9—C8	120.80 (18)	C11—C16—H16	119.6
N3—C10—C11	111.88 (15)

C9—N1—N2—N3	−0.1 (2)	N3—C4—C9—C8	177.98 (16)
N1—N2—N3—C4	−0.4 (2)	C5—C4—C9—C8	−2.1 (3)
N1—N2—N3—C10	179.31 (15)	C7—C8—C9—N1	−179.62 (19)
N2—N3—C4—C9	0.78 (18)	C7—C8—C9—C4	1.9 (3)
C10—N3—C4—C9	−178.94 (17)	N2—N3—C10—C11	106.88 (18)
N2—N3—C4—C5	−179.12 (18)	C4—N3—C10—C11	−73.4 (2)
C10—N3—C4—C5	1.2 (3)	N3—C10—C11—C16	−67.4 (2)
N3—C4—C5—C6	−179.41 (18)	N3—C10—C11—C12	113.53 (19)
C9—C4—C5—C6	0.7 (3)	C16—C11—C12—C13	−0.3 (3)
C4—C5—C6—C7	0.8 (3)	C10—C11—C12—C13	178.74 (17)
C5—C6—C7—C8	−1.0 (3)	C11—C12—C13—C14	−0.5 (3)
C6—C7—C8—C9	−0.4 (3)	C12—C13—C14—C15	0.8 (3)
N2—N1—C9—C4	0.6 (2)	C13—C14—C15—C16	−0.3 (3)
N2—N1—C9—C8	−178.05 (18)	C14—C15—C16—C11	−0.5 (3)
N3—C4—C9—N1	−0.84 (19)	C12—C11—C16—C15	0.9 (3)
C5—C4—C9—N1	179.07 (17)	C10—C11—C16—C15	−178.22 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1ⁱ	0.95	2.62	3.513 (3)	158
C14—H14···Cgⁱⁱ	0.95	2.69	3.583 (2)	157

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃
M_r	209.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	11.5734 (10), 5.9705 (4), 16.1202 (14)
β (°)	106.490 (4)
V (Å³)	1068.07 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (CORINC; Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994)
T_min, T_max	0.832, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	2125, 2020, 1788
R_int	0.108
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.138, 1.12
No. of reflections	2020
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1ⁱ	0.95	2.62	3.513 (3)	158
C14—H14···Cgⁱⁱ	0.95	2.69	3.583 (2)	157

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, y+1/2, −z+1/2.

References

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Volume 68| Part 4| April 2012| Page o1132

doi:10.1107/S1600536812010951

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