1-Benzyl-1H-benzotriazole 3-oxide-1-hy-droxy-1H-benzotriazole (1/1).

In the title compound, C(6)H(5)N(3)O·C(13)H(11)N(3)O, the benzo-triazole ring system in the 1-benzyl-1H-benzotriazole 3-oxide (A) mol-ecule is close to being planar (r.m.s. deviation = 0.011 Å); its mean plane forms a dihedral angle of 67.56 (7)° with that of the attached phenyl ring. The benzotriazole ring system in the 1-hy-droxy-benzotriazole (B) mol-ecule is also close to being planar (r.m.s. deviation = 0.010 Å). In the crystal, weak C-H⋯O and C-H⋯π inter-actions are present. The A and B molecules are linked by an O-H⋯N hydrogen bond.

Related literature

For related structures and background to benzotriazoles, see: Ravindran et al. (2009 ▶); Selvarathy Grace et al. (2012 ▶).

Experimental

Crystal data

C6H5N3O·C13H11N3O

M = 360.38

Monoclinic,

a = 11.2728 (8) Å

b = 12.2354 (5) Å

c = 13.1002 (9) Å

β = 110.946 (3)°

V = 1687.47 (18) Å3

Z = 4

Cu Kα radiation

μ = 0.80 mm−1

T = 193 K

0.40 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3364 measured reflections

3197 independent reflections

2980 reflections with I > 2σ(I)

R int = 0.102

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.08

3197 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030061/hb6878sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030061/hb6878Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030061/hb6878Isup3.cml

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

C6H5N3O·C13H11N3O	F(000) = 752
Mr = 360.38	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.2728 (8) Å	θ = 65–69°
b = 12.2354 (5) Å	µ = 0.80 mm−1
c = 13.1002 (9) Å	T = 193 K
β = 110.946 (3)°	Block, colourless
V = 1687.47 (18) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.102
Radiation source: rotating anode	θmax = 70.0°, θmin = 4.2°
Graphite monochromator	h = 0→13
ω/2θ scans	k = 0→14
3364 measured reflections	l = −15→14
3197 independent reflections	3 standard reflections every 60 min
2980 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0776P)2 + 0.6089P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3197 reflections	Δρmax = 0.35 e Å−3
245 parameters	Δρmin = −0.27 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: 0.0035 (5)

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	0.23017 (11)	0.44814 (10)	0.07382 (10)	0.0233 (3)
N2	0.21688 (11)	0.34031 (10)	0.08272 (10)	0.0261 (3)
N3	0.12730 (11)	0.32935 (10)	0.12460 (10)	0.0256 (3)
C1	0.08113 (13)	0.42800 (12)	0.14320 (11)	0.0231 (3)
C2	−0.01438 (14)	0.45549 (14)	0.18361 (13)	0.0314 (4)
H2	−0.0618	0.4017	0.2048	0.038*
C3	−0.03466 (15)	0.56486 (15)	0.19043 (13)	0.0351 (4)
H3	−0.0985	0.5880	0.2172	0.042*
C4	0.03627 (15)	0.64472 (14)	0.15895 (13)	0.0340 (4)
H4	0.0191	0.7197	0.1663	0.041*
C5	0.12920 (14)	0.61800 (12)	0.11806 (13)	0.0284 (3)
H5	0.1760	0.6719	0.0963	0.034*
C6	0.15024 (13)	0.50592 (11)	0.11070 (11)	0.0216 (3)
C7	0.32424 (14)	0.48951 (13)	0.02917 (12)	0.0285 (3)
H7A	0.2976	0.5627	−0.0030	0.034*
H7B	0.3269	0.4402	−0.0299	0.034*
C8	0.45521 (13)	0.49730 (12)	0.11541 (12)	0.0250 (3)
C9	0.50482 (15)	0.59795 (13)	0.15887 (14)	0.0327 (4)
H9	0.4566	0.6626	0.1333	0.039*
C10	0.62432 (17)	0.60451 (15)	0.23944 (15)	0.0384 (4)
H10	0.6576	0.6736	0.2691	0.046*
C11	0.69520 (15)	0.51109 (15)	0.27686 (13)	0.0368 (4)
H11	0.7768	0.5158	0.3326	0.044*
C12	0.64695 (16)	0.41032 (15)	0.23292 (15)	0.0379 (4)
H12	0.6957	0.3459	0.2583	0.045*
C13	0.52801 (15)	0.40353 (13)	0.15226 (14)	0.0323 (4)
H13	0.4957	0.3345	0.1217	0.039*
O1	0.09227 (11)	0.23257 (9)	0.14562 (11)	0.0383 (3)
N4	0.66756 (14)	0.18397 (12)	0.08895 (14)	0.0428 (4)
N5	0.75634 (14)	0.21667 (11)	0.05304 (14)	0.0417 (4)
N6	0.81861 (13)	0.12778 (10)	0.03929 (12)	0.0312 (3)
C14	0.77039 (14)	0.03437 (12)	0.06416 (12)	0.0252 (3)
C15	0.79910 (16)	−0.07638 (13)	0.06063 (13)	0.0329 (4)
H15	0.8655	−0.1009	0.0377	0.039*
C16	0.72455 (18)	−0.14724 (13)	0.09268 (14)	0.0372 (4)
H16	0.7400	−0.2235	0.0921	0.045*
C17	0.62562 (17)	−0.11034 (15)	0.12655 (14)	0.0378 (4)
H17	0.5768	−0.1625	0.1482	0.045*
C18	0.59823 (16)	−0.00226 (15)	0.12905 (14)	0.0353 (4)
H18	0.5313	0.0218	0.1516	0.042*
C19	0.67306 (15)	0.07221 (13)	0.09693 (13)	0.0293 (3)
O2	0.91290 (12)	0.13654 (10)	−0.00258 (11)	0.0419 (3)
H2A	0.9753	0.1692	0.0424	0.063*

	U11	U22	U33	U12	U13	U23
N1	0.0237 (6)	0.0214 (6)	0.0286 (6)	−0.0013 (5)	0.0138 (5)	0.0007 (5)
N2	0.0253 (6)	0.0211 (6)	0.0344 (7)	−0.0006 (5)	0.0139 (5)	−0.0006 (5)
N3	0.0235 (6)	0.0201 (6)	0.0339 (7)	−0.0012 (4)	0.0112 (5)	0.0047 (5)
C1	0.0217 (6)	0.0232 (7)	0.0246 (7)	0.0012 (5)	0.0086 (5)	0.0035 (5)
C2	0.0267 (7)	0.0391 (9)	0.0321 (8)	0.0020 (6)	0.0150 (6)	0.0055 (7)
C3	0.0309 (8)	0.0452 (10)	0.0327 (8)	0.0095 (7)	0.0157 (7)	−0.0010 (7)
C4	0.0361 (8)	0.0288 (8)	0.0355 (8)	0.0080 (6)	0.0109 (7)	−0.0055 (6)
C5	0.0311 (8)	0.0215 (7)	0.0322 (8)	−0.0004 (6)	0.0108 (6)	0.0006 (6)
C6	0.0210 (6)	0.0215 (7)	0.0226 (7)	0.0002 (5)	0.0081 (5)	0.0004 (5)
C7	0.0290 (8)	0.0327 (8)	0.0294 (8)	−0.0041 (6)	0.0173 (6)	0.0016 (6)
C8	0.0264 (7)	0.0273 (7)	0.0280 (7)	−0.0023 (6)	0.0179 (6)	−0.0000 (6)
C9	0.0350 (8)	0.0258 (8)	0.0426 (9)	−0.0038 (6)	0.0203 (7)	0.0017 (6)
C10	0.0405 (9)	0.0372 (9)	0.0416 (9)	−0.0148 (7)	0.0197 (7)	−0.0068 (7)
C11	0.0292 (8)	0.0537 (11)	0.0301 (8)	−0.0065 (7)	0.0138 (6)	0.0012 (7)
C12	0.0342 (8)	0.0414 (9)	0.0415 (9)	0.0066 (7)	0.0177 (7)	0.0076 (7)
C13	0.0334 (8)	0.0287 (8)	0.0407 (9)	0.0001 (6)	0.0206 (7)	−0.0030 (6)
O1	0.0371 (6)	0.0216 (6)	0.0573 (8)	−0.0058 (4)	0.0181 (5)	0.0105 (5)
N4	0.0421 (8)	0.0264 (7)	0.0647 (10)	0.0033 (6)	0.0249 (7)	−0.0049 (7)
N5	0.0449 (8)	0.0207 (7)	0.0623 (10)	0.0006 (6)	0.0225 (7)	0.0008 (6)
N6	0.0332 (7)	0.0223 (6)	0.0432 (8)	−0.0021 (5)	0.0199 (6)	0.0021 (5)
C14	0.0301 (7)	0.0211 (7)	0.0261 (7)	−0.0034 (6)	0.0121 (6)	−0.0010 (5)
C15	0.0427 (9)	0.0258 (8)	0.0357 (8)	0.0037 (7)	0.0208 (7)	−0.0014 (6)
C16	0.0550 (11)	0.0203 (7)	0.0382 (9)	−0.0034 (7)	0.0189 (8)	−0.0006 (6)
C17	0.0452 (10)	0.0367 (9)	0.0342 (9)	−0.0141 (7)	0.0175 (7)	0.0008 (7)
C18	0.0343 (8)	0.0419 (9)	0.0350 (9)	−0.0054 (7)	0.0187 (7)	−0.0043 (7)
C19	0.0313 (8)	0.0247 (8)	0.0327 (8)	0.0001 (6)	0.0124 (6)	−0.0043 (6)
O2	0.0451 (7)	0.0395 (7)	0.0521 (7)	−0.0101 (5)	0.0309 (6)	−0.0005 (6)

N1—N2	1.3376 (17)	C10—H10	0.9500
N1—C6	1.3625 (18)	C11—C12	1.387 (3)
N1—C7	1.4718 (17)	C11—H11	0.9500
N2—N3	1.3171 (17)	C12—C13	1.381 (2)
N3—O1	1.3082 (16)	C12—H12	0.9500
N3—C1	1.3703 (19)	C13—H13	0.9500
C1—C6	1.391 (2)	N4—N5	1.311 (2)
C1—C2	1.400 (2)	N4—C19	1.371 (2)
C2—C3	1.366 (2)	N5—N6	1.3411 (19)
C2—H2	0.9500	N6—C14	1.3545 (19)
C3—C4	1.414 (3)	N6—O2	1.3635 (17)
C3—H3	0.9500	C14—C19	1.393 (2)
C4—C5	1.376 (2)	C14—C15	1.398 (2)
C4—H4	0.9500	C15—C16	1.373 (2)
C5—C6	1.401 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.414 (3)
C7—H7A	0.9900	C16—H16	0.9500
C7—H7B	0.9900	C17—C18	1.361 (3)
C8—C9	1.388 (2)	C17—H17	0.9500
C8—C13	1.393 (2)	C18—C19	1.404 (2)
C9—H9	0.9500	C18—H18	0.9500
C10—C11	1.380 (3)	O2—H2A	0.8400
N2—N1—C6	111.83 (11)	C11—C10—C9	120.30 (16)
N2—N1—C7	119.53 (12)	C11—C10—H10	119.9
C6—N1—C7	128.63 (12)	C9—C10—H10	119.9
N3—N2—N1	105.26 (11)	C10—C11—C12	119.83 (16)
O1—N3—N2	120.92 (12)	C10—C11—H11	120.1
O1—N3—C1	126.69 (12)	C12—C11—H11	120.1
N2—N3—C1	112.38 (12)	C13—C12—C11	120.02 (16)
N3—C1—C6	105.04 (12)	C13—C12—H12	120.0
N3—C1—C2	132.16 (14)	C11—C12—H12	120.0
C6—C1—C2	122.80 (14)	C12—C13—C8	120.41 (15)
C3—C2—C1	115.44 (15)	C12—C13—H13	119.8
C3—C2—H2	122.3	C8—C13—H13	119.8
C1—C2—H2	122.3	N5—N4—C19	108.20 (14)
C2—C3—C4	122.17 (15)	N4—N5—N6	107.69 (13)
C2—C3—H3	118.9	N5—N6—C14	112.19 (13)
C4—C3—H3	118.9	N5—N6—O2	120.74 (13)
C5—C4—C3	122.55 (15)	C14—N6—O2	126.92 (13)
C5—C4—H4	118.7	N6—C14—C19	102.81 (13)
C3—C4—H4	118.7	N6—C14—C15	133.83 (14)
C4—C5—C6	115.51 (14)	C19—C14—C15	123.35 (14)
C4—C5—H5	122.2	C16—C15—C14	115.32 (15)
C6—C5—H5	122.2	C16—C15—H15	122.3
N1—C6—C1	105.47 (12)	C14—C15—H15	122.3
N1—C6—C5	133.00 (14)	C15—C16—C17	122.14 (15)
C1—C6—C5	121.52 (13)	C15—C16—H16	118.9
N1—C7—C8	112.06 (12)	C17—C16—H16	118.9
N1—C7—H7A	109.2	C18—C17—C16	121.94 (16)
C8—C7—H7A	109.2	C18—C17—H17	119.0
N1—C7—H7B	109.2	C16—C17—H17	119.0
C8—C7—H7B	109.2	C17—C18—C19	117.22 (15)
H7A—C7—H7B	107.9	C17—C18—H18	121.4
C9—C8—C13	119.20 (14)	C19—C18—H18	121.4
C9—C8—C7	120.43 (14)	N4—C19—C14	109.10 (14)
C13—C8—C7	120.37 (14)	N4—C19—C18	130.86 (15)
C10—C9—C8	120.23 (15)	C14—C19—C18	120.03 (15)
C10—C9—H9	119.9	N6—O2—H2A	109.5
C8—C9—H9	119.9
C6—N1—N2—N3	0.52 (15)	C7—C8—C9—C10	178.88 (14)
C7—N1—N2—N3	179.96 (12)	C8—C9—C10—C11	0.2 (3)
N1—N2—N3—O1	−178.89 (12)	C9—C10—C11—C12	0.5 (3)
N1—N2—N3—C1	0.15 (16)	C10—C11—C12—C13	−0.3 (3)
O1—N3—C1—C6	178.25 (13)	C11—C12—C13—C8	−0.7 (2)
N2—N3—C1—C6	−0.73 (16)	C9—C8—C13—C12	1.5 (2)
O1—N3—C1—C2	−2.6 (3)	C7—C8—C13—C12	−178.64 (14)
N2—N3—C1—C2	178.37 (15)	C19—N4—N5—N6	−0.6 (2)
N3—C1—C2—C3	−179.72 (15)	N4—N5—N6—C14	1.1 (2)
C6—C1—C2—C3	−0.8 (2)	N4—N5—N6—O2	176.88 (14)
C1—C2—C3—C4	−0.1 (2)	N5—N6—C14—C19	−1.03 (18)
C2—C3—C4—C5	0.9 (3)	O2—N6—C14—C19	−176.51 (14)
C3—C4—C5—C6	−0.7 (2)	N5—N6—C14—C15	178.09 (17)
N2—N1—C6—C1	−0.96 (15)	O2—N6—C14—C15	2.6 (3)
C7—N1—C6—C1	179.66 (13)	N6—C14—C15—C16	−179.35 (17)
N2—N1—C6—C5	−179.96 (15)	C19—C14—C15—C16	−0.4 (2)
C7—N1—C6—C5	0.7 (3)	C14—C15—C16—C17	0.1 (2)
N3—C1—C6—N1	0.98 (15)	C15—C16—C17—C18	0.2 (3)
C2—C1—C6—N1	−178.23 (13)	C16—C17—C18—C19	−0.3 (3)
N3—C1—C6—C5	−179.87 (13)	N5—N4—C19—C14	−0.01 (19)
C2—C1—C6—C5	0.9 (2)	N5—N4—C19—C18	−178.73 (17)
C4—C5—C6—N1	178.71 (15)	N6—C14—C19—N4	0.61 (17)
C4—C5—C6—C1	−0.2 (2)	C15—C14—C19—N4	−178.63 (15)
C6—N1—C7—C8	94.88 (17)	N6—C14—C19—C18	179.50 (14)
N1—C7—C8—C9	−104.04 (16)	C15—C14—C19—C18	0.3 (2)
N1—C7—C8—C13	76.11 (17)	C17—C18—C19—N4	178.71 (17)
C13—C8—C9—C10	−1.3 (2)	C17—C18—C19—C14	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N3i	0.84	2.57	3.3621 (18)	157
C3—H3···O1ii	0.95	2.50	3.200 (2)	130
C7—H7B···Cg1iii	0.99	2.85	3.5146 (17)	125
C18—H18···Cg1iv	0.95	2.69	3.510 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N3i	0.84	2.57	3.3621 (18)	157
C3—H3⋯O1ii	0.95	2.50	3.200 (2)	130
C7—H7B⋯Cg1iii	0.99	2.85	3.5146 (17)	125
C18—H18⋯Cg1iv	0.95	2.69	3.510 (2)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .