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

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 methyl-ene group, forming a dihedral angle of 81.87 (15)°. In the crystal, mol-ecules 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] inter-actions.

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 = 243.26

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.140

S = 0.98

1677 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044868/tk5165sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044868/tk5165Isup3.cml

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

C13H11N3O·H2O	F(000) = 512
Mr = 243.26	Dx = 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

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

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(Fo2) + (0.0825P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
1677 reflections	Δρmax = 0.19 e Å−3
164 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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⋯O1W i	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) ; (ii) ; (iii) .