4-(4-Hydroxy-phenyl-diazen-yl)-benzonitrile.

The molecule of the title compound, C(13)H(9)N(3)O, is achiral but forms a chiral arrangement in the crystal structure. The mol-ecule adopts an E configuration with respect to the N=N bond and is almost planar, with an r.m.s. deviation of 0.0439 Å from the plane through all atoms in the mol-ecule. The dihedral angle between the two benzene rings is 2.2 (2)°. In the crystal structure, inter-molecular O-H⋯N hydrogen bonding generates a chain.

Related literature

For the preparation of tetra­zole derivatives from nitrile compounds, see: Dunica et al. (1991 ▶); Wittenberger & Donner (1993 ▶). For the general chemistry of tetra­zole compounds, see: Xiong et al. (2002 ▶). For a similar structure, see: Harada et al. (1997 ▶).

Experimental

Crystal data

C13H9N3O

M = 223.23

Monoclinic,

a = 6.5307 (13) Å

b = 10.747 (2) Å

c = 15.851 (3) Å

β = 93.54 (3)°

V = 1110.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.18 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.781, T max = 1 (expected range = 0.778–0.996)

5599 measured reflections

2532 independent reflections

1296 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.145

S = 0.97

1278 reflections

154 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004716/kp2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004716/kp2153Isup2.hkl

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

C13H9N3O	F000 = 464
Mr = 223.23	Dx = 1.335 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4352 reflections
a = 6.5307 (13) Å	θ = 3.7–27.7º
b = 10.747 (2) Å	µ = 0.09 mm−1
c = 15.851 (3) Å	T = 293 (2) K
β = 93.54 (3)º	BLOCK, yellow
V = 1110.4 (4) Å3	0.18 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	2532 independent reflections
Radiation source: fine-focus sealed tube	1296 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.073
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.7º
ω scans	h = −8→8
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.781, Tmax = 1	l = −20→20
5599 measured reflections

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0762P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
1278 reflections	Δρmax = 0.17 e Å−3
154 parameters	Δρmin = −0.19 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: indeterminate

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N3	0.2824 (5)	0.0455 (4)	0.1896 (2)	0.0497 (10)
N2	0.1650 (5)	0.1302 (4)	0.1608 (2)	0.0526 (11)
C8	0.4581 (6)	0.0892 (5)	0.2376 (3)	0.0447 (11)
O1	0.9855 (5)	0.1997 (4)	0.3729 (2)	0.0717 (11)
H1A	1.0618	0.1372	0.3848	0.108*
C3	−0.3689 (6)	0.0230 (5)	0.0211 (3)	0.0493 (12)
C7	−0.0130 (6)	0.0862 (4)	0.1136 (3)	0.0457 (11)
C12	0.7767 (7)	0.0358 (5)	0.3110 (3)	0.0502 (11)
H12A	0.8709	−0.0242	0.3303	0.060*
C4	−0.5570 (7)	−0.0106 (5)	−0.0251 (3)	0.0572 (13)
C6	−0.0538 (7)	−0.0375 (5)	0.0957 (3)	0.0543 (13)
H6A	0.0385	−0.0988	0.1146	0.065*
C2	−0.3273 (7)	0.1461 (5)	0.0391 (3)	0.0583 (14)
H2B	−0.4188	0.2075	0.0197	0.070*
C5	−0.2315 (6)	−0.0695 (5)	0.0497 (3)	0.0565 (14)
H5A	−0.2600	−0.1526	0.0377	0.068*
C9	0.4922 (6)	0.2126 (4)	0.2580 (3)	0.0577 (13)
H9A	0.3959	0.2725	0.2407	0.069*
C11	0.8129 (7)	0.1589 (4)	0.3289 (3)	0.0513 (12)
C13	0.6011 (7)	0.0010 (5)	0.2644 (3)	0.0519 (13)
H13A	0.5788	−0.0823	0.2511	0.062*
C10	0.6682 (7)	0.2471 (5)	0.3040 (3)	0.0622 (15)
H10A	0.6898	0.3302	0.3183	0.075*
N1	−0.7085 (7)	−0.0361 (5)	−0.0604 (3)	0.0712 (12)
C1	−0.1502 (7)	0.1783 (5)	0.0860 (3)	0.0580 (14)
H1B	−0.1228	0.2613	0.0990	0.070*

	U11	U22	U33	U12	U13	U23
N3	0.041 (2)	0.055 (3)	0.051 (2)	0.000 (2)	−0.0098 (18)	0.0033 (19)
N2	0.043 (2)	0.054 (3)	0.059 (3)	0.002 (2)	−0.0175 (19)	0.001 (2)
C8	0.031 (2)	0.051 (3)	0.051 (3)	0.0005 (19)	−0.008 (2)	0.000 (2)
O1	0.055 (2)	0.071 (3)	0.084 (3)	0.0087 (18)	−0.0356 (19)	−0.014 (2)
C3	0.035 (2)	0.070 (4)	0.041 (2)	−0.005 (2)	−0.0080 (19)	0.000 (2)
C7	0.042 (3)	0.055 (3)	0.039 (3)	−0.002 (2)	−0.010 (2)	0.003 (2)
C12	0.039 (3)	0.055 (3)	0.055 (3)	0.008 (2)	−0.012 (2)	0.003 (2)
C4	0.046 (3)	0.072 (4)	0.052 (3)	−0.006 (3)	−0.006 (2)	−0.001 (2)
C6	0.045 (3)	0.053 (3)	0.063 (3)	0.007 (2)	−0.017 (2)	−0.004 (3)
C2	0.054 (3)	0.057 (3)	0.061 (3)	0.006 (2)	−0.019 (2)	0.003 (2)
C5	0.053 (3)	0.054 (3)	0.060 (3)	0.000 (2)	−0.009 (2)	−0.012 (2)
C9	0.045 (3)	0.049 (3)	0.076 (4)	0.007 (2)	−0.023 (2)	0.001 (3)
C11	0.046 (3)	0.057 (3)	0.049 (3)	−0.003 (2)	−0.010 (2)	−0.006 (2)
C13	0.045 (3)	0.049 (3)	0.061 (3)	0.008 (2)	−0.007 (2)	−0.007 (2)
C10	0.055 (3)	0.050 (3)	0.078 (4)	0.005 (2)	−0.021 (3)	−0.004 (3)
N1	0.048 (2)	0.091 (3)	0.072 (3)	−0.013 (2)	−0.017 (2)	−0.007 (2)
C1	0.051 (3)	0.049 (3)	0.071 (4)	−0.004 (2)	−0.021 (3)	0.008 (2)

N3—N2	1.258 (4)	C12—H12A	0.9300
N3—C8	1.417 (5)	C4—N1	1.140 (6)
N2—C7	1.424 (5)	C6—C5	1.375 (7)
C8—C13	1.380 (6)	C6—H6A	0.9300
C8—C9	1.380 (6)	C2—C1	1.380 (6)
O1—C11	1.361 (5)	C2—H2B	0.9300
O1—H1A	0.8501	C5—H5A	0.9300
C3—C2	1.377 (7)	C9—C10	1.373 (6)
C3—C5	1.395 (7)	C9—H9A	0.9300
C3—C4	1.437 (6)	C11—C10	1.379 (7)
C7—C6	1.382 (6)	C13—H13A	0.9300
C7—C1	1.388 (6)	C10—H10A	0.9300
C12—C11	1.371 (7)	C1—H1B	0.9300
C12—C13	1.377 (7)
N2—N3—C8	114.2 (3)	C3—C2—H2B	120.0
N3—N2—C7	114.2 (3)	C1—C2—H2B	120.0
C13—C8—C9	119.4 (4)	C6—C5—C3	119.9 (4)
C13—C8—N3	116.6 (4)	C6—C5—H5A	120.0
C9—C8—N3	124.0 (4)	C3—C5—H5A	120.0
C11—O1—H1A	108.4	C10—C9—C8	120.1 (4)
C2—C3—C5	120.1 (4)	C10—C9—H9A	119.9
C2—C3—C4	119.9 (4)	C8—C9—H9A	119.9
C5—C3—C4	119.9 (5)	O1—C11—C12	122.9 (4)
C6—C7—C1	120.6 (4)	O1—C11—C10	117.2 (4)
C6—C7—N2	124.6 (4)	C12—C11—C10	119.9 (4)
C1—C7—N2	114.8 (4)	C12—C13—C8	120.3 (5)
C11—C12—C13	120.0 (4)	C12—C13—H13A	119.8
C11—C12—H12A	120.0	C8—C13—H13A	119.8
C13—C12—H12A	120.0	C9—C10—C11	120.2 (4)
N1—C4—C3	178.5 (6)	C9—C10—H10A	119.9
C5—C6—C7	119.7 (4)	C11—C10—H10A	119.9
C5—C6—H6A	120.2	C2—C1—C7	119.6 (5)
C7—C6—H6A	120.2	C2—C1—H1B	120.2
C3—C2—C1	120.0 (4)	C7—C1—H1B	120.2
C7—N2—N3—C8	−179.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.85	2.01	2.817 (5)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.85	2.01	2.817 (5)	159

Symmetry code: (i) .