1-Benzyl-1H-benzotriazole 3-oxide monohydrate

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

doi:10.1107/S1600536812044868

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3297

doi:10.1107/S1600536812044868

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1-Benzyl-1H-benzotriazole 3-oxide monohydrate

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 Government 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 27 October 2012; accepted 30 October 2012; online 7 November 2012)

In the title hydrate, C₁₃H₁₁N₃O·H₂O, the benzotriazole ring system is planar (r.m.s. deviation = 0.007 Å) and is almost orthogonal to the phenyl ring to which it is linked by a methylene group, forming a dihedral angle of 81.87 (15)°. In the crystal, molecules are linked into chains along [001] by O—H⋯O hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H⋯O, C—H⋯π and π–π [centroid–centroid distance between the five- and six-membered rings of the benzotriazole ring system = 3.595 (3) Å] interactions.

Related literature

For the biological activity of benzotriazole derivatives, see: Kopańska 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: Selvarathy Grace et al. (2012 ).

Experimental

Crystal data

C₁₃H₁₁N₃O·H₂O
M_r = 243.26
Orthorhombic, P n a 2₁
a = 12.556 (5) Å
b = 20.881 (8) Å
c = 4.6651 (18) Å
V = 1223.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.40 × 0.05 × 0.04 mm

Data collection

Bruker SMART APEXII diffractometer
15911 measured reflections
1677 independent reflections
1118 reflections with I > 2σ(I)
R_int = 0.132

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.140
S = 0.98
1677 reflections
164 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O1Wⁱ	0.82	1.93	2.744 (3)	169
O1W—H2W⋯O17	0.85	1.95	2.800 (3)	180
C10—H10A⋯O17ⁱⁱ	0.99	2.45	3.400 (5)	161
C10—H10B⋯Cg3ⁱⁱⁱ	0.99	2.51	3.382 (4)	147
Symmetry codes: (i) $[-x+1, -y, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (iii) x, y, z-1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044868/tk5165sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044868/tk5165Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812044868/tk5165Isup3.cml

checkCIF report

Comment top

Benzotriazole derivatives show biological activities such as anti-inflammatory, diuretic, anti-viral and anti-hypertensive (Kopańska et al., 2005; Sarala et al., 2007). They have been used as a corrosion inhibitor, anti-freeze agent, ultraviolet light stabilizer for plastics and as an anti-foggant 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 anti-fouling and anti-wear reagent (Sha et al., 1996). Due to the above mentioned applications of benzotriazole, we have systematically synthesised and investigated the structures of novel benzotriazole derivatives. We have already reported the crystal structure of 1-(benzyl)-1H-benzotriazole (Selvarathy Grace et al., 2012). Here, we report the crystal structure of the title compound (I).

The benzotriazole ring in (I), Fig 1, is essentially planar with the maximum deviation from planarity being 0.010 (3) Å for atom N3. The mean plane of the benzotriazole ring (N1–N3,C4–C9) forms a dihedral angle of 81.87 (15) Å with the mean plane of the phenyl ring (C11–C16).

The molecules are linked into a one dimensional chain along [001] by O—H···O hydrogen bonds, Table 1 and Fig. 2. The crystal packing is stabilized by π–π stacking interactions with the centroid-centroid distance of 3.595 (3) Å [symmetry code: x, y, -1+z], together with C—H···O and C—H···π interactions, Table 1.

Related literature top

For the biological activity of benzotriazole derivatives, see: Kopańska 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: Selvarathy Grace et al. (2012).

Experimental top

A mixture of sodium salt of 1-hydroxyl benzotriazole (0.157 g, 1 mmol) and benzyl chloride (0.126 g, 1 mmol) in a mixture comprising ethanol, water and sodium ethoxide (10 ml) were heated at 333 K with continuous stirring for 6 h. The mixture was kept aside for slow evaporation. After a week, crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, highlighting the one-dimensional chains along [001]. Hydrogen bonds are shown as dashed lines.

1-Benzyl-1H-benzotriazole 3-oxide monohydrate top

Crystal data top

C₁₃H₁₁N₃O·H₂O	F(000) = 512
M_r = 243.26	D_x = 1.321 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1403 reflections
a = 12.556 (5) Å	θ = 2.5–20.2°
b = 20.881 (8) Å	µ = 0.09 mm⁻¹
c = 4.6651 (18) Å	T = 173 K
V = 1223.1 (8) Å³	Needle, colourless
Z = 4	0.40 × 0.05 × 0.04 mm

Data collection top

Bruker SMART APEXII diffractometer	1118 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.132
Graphite monochromator	θ_max = 28.2°, θ_min = 1.9°
CCD scan	h = −16→16
15911 measured reflections	k = −27→27
1677 independent reflections	l = −6→6

Refinement top

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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0825P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
1677 reflections	Δρ_max = 0.19 e Å⁻³
164 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (6)

Crystal data top

C₁₃H₁₁N₃O·H₂O	V = 1223.1 (8) Å³
M_r = 243.26	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.556 (5) Å	µ = 0.09 mm⁻¹
b = 20.881 (8) Å	T = 173 K
c = 4.6651 (18) Å	0.40 × 0.05 × 0.04 mm

Data collection top

Bruker SMART APEXII diffractometer	1118 reflections with I > 2σ(I)
15911 measured reflections	R_int = 0.132
1677 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.140	H-atom parameters constrained
S = 0.98	Δρ_max = 0.19 e Å⁻³
1677 reflections	Δρ_min = −0.24 e Å⁻³
164 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	0.3160 (2)	0.27237 (12)	0.6604 (7)	0.0335 (7)
N2	0.4106 (2)	0.25008 (13)	0.5616 (7)	0.0372 (7)
N3	0.4253 (2)	0.19473 (13)	0.6976 (8)	0.0389 (8)
C4	0.3429 (3)	0.18041 (15)	0.8807 (9)	0.0343 (8)
C5	0.3241 (3)	0.12821 (16)	1.0631 (10)	0.0455 (10)
H5	0.3720	0.0931	1.0769	0.055*
C6	0.2315 (3)	0.13125 (18)	1.2207 (10)	0.0524 (11)
H6	0.2153	0.0974	1.3495	0.063*
C7	0.1594 (3)	0.18339 (18)	1.1969 (10)	0.0464 (9)
H7	0.0962	0.1829	1.3089	0.056*
C8	0.1776 (3)	0.23429 (16)	1.0183 (8)	0.0380 (9)
H8	0.1293	0.2692	1.0038	0.046*
C9	0.2720 (3)	0.23174 (14)	0.8583 (8)	0.0301 (8)
C10	0.2800 (3)	0.33671 (14)	0.5809 (9)	0.0344 (8)
H10A	0.2019	0.3360	0.5514	0.041*
H10B	0.3137	0.3492	0.3974	0.041*
C11	0.3069 (3)	0.38601 (15)	0.8068 (8)	0.0310 (8)
C12	0.2259 (3)	0.42481 (15)	0.9188 (9)	0.0364 (8)
H12	0.1545	0.4193	0.8558	0.044*
C13	0.2499 (3)	0.47148 (15)	1.1226 (9)	0.0419 (9)
H13	0.1948	0.4979	1.1972	0.050*
C14	0.3532 (3)	0.47944 (16)	1.2161 (10)	0.0423 (9)
H14	0.3693	0.5115	1.3539	0.051*
C15	0.4335 (3)	0.44073 (16)	1.1095 (9)	0.0396 (9)
H15	0.5044	0.4458	1.1767	0.048*
C16	0.4107 (3)	0.39448 (16)	0.9047 (9)	0.0377 (8)
H16	0.4663	0.3684	0.8308	0.045*
O17	0.51045 (19)	0.16046 (12)	0.6496 (9)	0.0576 (10)
O1W	0.4934 (2)	0.03436 (11)	0.4506 (7)	0.0472 (7)
H1W	0.4943	0.0098	0.5883	0.071*
H2W	0.4986	0.0728	0.5103	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0399 (15)	0.0262 (13)	0.0344 (17)	0.0007 (12)	−0.0016 (14)	0.0040 (13)
N2	0.0383 (15)	0.0306 (13)	0.0426 (18)	0.0002 (13)	0.0004 (15)	−0.0061 (14)
N3	0.0389 (15)	0.0276 (13)	0.0503 (19)	0.0033 (12)	−0.0076 (16)	−0.0087 (15)
C4	0.0400 (18)	0.0240 (15)	0.039 (2)	−0.0013 (14)	−0.0091 (18)	−0.0034 (16)
C5	0.063 (2)	0.0263 (16)	0.048 (2)	−0.0027 (17)	−0.021 (2)	0.0027 (18)
C6	0.080 (3)	0.034 (2)	0.043 (2)	−0.017 (2)	−0.018 (3)	0.0126 (19)
C7	0.056 (2)	0.043 (2)	0.039 (2)	−0.0120 (17)	−0.003 (2)	0.008 (2)
C8	0.044 (2)	0.0316 (18)	0.038 (2)	−0.0022 (15)	−0.0036 (18)	0.0001 (16)
C9	0.0396 (18)	0.0241 (14)	0.0268 (19)	−0.0015 (13)	−0.0043 (16)	0.0025 (14)
C10	0.045 (2)	0.0259 (15)	0.0321 (19)	0.0012 (14)	−0.0032 (17)	0.0053 (15)
C11	0.0410 (18)	0.0214 (14)	0.0304 (18)	−0.0046 (14)	−0.0022 (16)	0.0067 (14)
C12	0.0353 (17)	0.0297 (15)	0.044 (2)	0.0020 (14)	−0.0066 (18)	0.0010 (17)
C13	0.0461 (19)	0.0287 (16)	0.051 (3)	0.0061 (15)	−0.005 (2)	−0.0025 (18)
C14	0.056 (2)	0.0299 (16)	0.041 (2)	−0.0108 (16)	−0.001 (2)	−0.0005 (18)
C15	0.0401 (19)	0.0376 (17)	0.041 (2)	−0.0109 (16)	−0.0017 (18)	0.0010 (17)
C16	0.0376 (18)	0.0372 (17)	0.038 (2)	0.0002 (15)	0.0028 (17)	0.0048 (17)
O17	0.0404 (14)	0.0367 (13)	0.096 (3)	0.0084 (11)	−0.0063 (17)	−0.0224 (18)
O1W	0.0745 (18)	0.0287 (12)	0.0382 (15)	−0.0030 (12)	−0.0035 (14)	−0.0018 (12)

Geometric parameters (Å, º) top

N1—N2	1.356 (4)	C10—H10A	0.9900
N1—C9	1.370 (4)	C10—H10B	0.9900
N1—C10	1.465 (4)	C11—C16	1.393 (5)
N2—N3	1.331 (4)	C11—C12	1.401 (5)
N3—O17	1.306 (4)	C12—C13	1.394 (5)
N3—C4	1.374 (5)	C12—H12	0.9500
C4—C9	1.398 (4)	C13—C14	1.379 (5)
C4—C5	1.403 (5)	C13—H13	0.9500
C5—C6	1.377 (6)	C14—C15	1.385 (5)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.421 (6)	C15—C16	1.389 (5)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.370 (5)	C16—H16	0.9500
C7—H7	0.9500	O1W—H1W	0.8225
C8—C9	1.401 (5)	O1W—H2W	0.8519
C8—H8	0.9500

N2—N1—C9	111.7 (3)	N1—C10—C11	112.3 (3)
N2—N1—C10	119.9 (3)	N1—C10—H10A	109.1
C9—N1—C10	127.8 (3)	C11—C10—H10A	109.1
N3—N2—N1	104.9 (3)	N1—C10—H10B	109.1
O17—N3—N2	120.5 (3)	C11—C10—H10B	109.1
O17—N3—C4	127.1 (3)	H10A—C10—H10B	107.9
N2—N3—C4	112.4 (3)	C16—C11—C12	118.9 (3)
N3—C4—C9	105.4 (3)	C16—C11—C10	121.6 (3)
N3—C4—C5	132.3 (3)	C12—C11—C10	119.5 (3)
C9—C4—C5	122.3 (3)	C13—C12—C11	120.1 (3)
C6—C5—C4	115.5 (3)	C13—C12—H12	119.9
C6—C5—H5	122.3	C11—C12—H12	119.9
C4—C5—H5	122.3	C14—C13—C12	120.2 (3)
C5—C6—C7	122.1 (4)	C14—C13—H13	119.9
C5—C6—H6	118.9	C12—C13—H13	119.9
C7—C6—H6	118.9	C13—C14—C15	120.1 (4)
C8—C7—C6	122.4 (4)	C13—C14—H14	120.0
C8—C7—H7	118.8	C15—C14—H14	120.0
C6—C7—H7	118.8	C14—C15—C16	120.2 (3)
C7—C8—C9	115.9 (3)	C14—C15—H15	119.9
C7—C8—H8	122.1	C16—C15—H15	119.9
C9—C8—H8	122.1	C15—C16—C11	120.5 (3)
N1—C9—C4	105.5 (3)	C15—C16—H16	119.8
N1—C9—C8	132.6 (3)	C11—C16—H16	119.8
C4—C9—C8	121.9 (3)	H1W—O1W—H2W	109.4

C9—N1—N2—N3	0.5 (4)	C5—C4—C9—N1	−179.4 (3)
C10—N1—N2—N3	172.9 (3)	N3—C4—C9—C8	−179.3 (3)
N1—N2—N3—O17	179.9 (3)	C5—C4—C9—C8	0.3 (5)
N1—N2—N3—C4	0.2 (4)	C7—C8—C9—N1	179.4 (4)
O17—N3—C4—C9	179.6 (3)	C7—C8—C9—C4	−0.1 (5)
N2—N3—C4—C9	−0.8 (4)	N2—N1—C10—C11	−96.1 (4)
O17—N3—C4—C5	0.0 (7)	C9—N1—C10—C11	74.9 (4)
N2—N3—C4—C5	179.6 (4)	N1—C10—C11—C16	54.8 (4)
N3—C4—C5—C6	178.9 (4)	N1—C10—C11—C12	−126.0 (3)
C9—C4—C5—C6	−0.6 (5)	C16—C11—C12—C13	0.7 (5)
C4—C5—C6—C7	0.8 (6)	C10—C11—C12—C13	−178.6 (3)
C5—C6—C7—C8	−0.7 (6)	C11—C12—C13—C14	−0.4 (6)
C6—C7—C8—C9	0.3 (6)	C12—C13—C14—C15	−0.5 (6)
N2—N1—C9—C4	−1.0 (4)	C13—C14—C15—C16	1.0 (6)
C10—N1—C9—C4	−172.6 (3)	C14—C15—C16—C11	−0.7 (6)
N2—N1—C9—C8	179.5 (4)	C12—C11—C16—C15	−0.1 (5)
C10—N1—C9—C8	7.8 (6)	C10—C11—C16—C15	179.1 (3)
N3—C4—C9—N1	1.0 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1Wⁱ	0.82	1.93	2.744 (3)	169
O1W—H2W···O17	0.85	1.95	2.800 (3)	180
C10—H10A···O17ⁱⁱ	0.99	2.45	3.400 (5)	161
C10—H10B···Cg3ⁱⁱⁱ	0.99	2.51	3.382 (4)	147

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O·H₂O
M_r	243.26
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	173
a, b, c (Å)	12.556 (5), 20.881 (8), 4.6651 (18)
V (Å³)	1223.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.05 × 0.04

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15911, 1677, 1118
R_int	0.132
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.140, 0.98
No. of reflections	1677
No. of parameters	164
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1Wⁱ	0.82	1.93	2.744 (3)	169
O1W—H2W···O17	0.85	1.95	2.800 (3)	180
C10—H10A···O17ⁱⁱ	0.99	2.45	3.400 (5)	161
C10—H10B···Cg3ⁱⁱⁱ	0.99	2.51	3.382 (4)	147

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

References

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Volume 68| Part 12| December 2012| Page o3297

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