4-(4-Hydroxy­phenyl­diazen­yl)­benzonitrile

Zhang, C.Z.

doi:10.1107/S1600536808004716

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o618

doi:10.1107/S1600536808004716

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4-(4-Hydroxyphenyldiazenyl)benzonitrile

Chao Zhi Zhang ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: zhangchaozhi@seu.edu.cn

(Received 1 December 2007; accepted 18 February 2008; online 22 February 2008)

The molecule of the title compound, C₁₃H₉N₃O, is achiral but forms a chiral arrangement in the crystal structure. The molecule 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 molecule. The dihedral angle between the two benzene rings is 2.2 (2)°. In the crystal structure, intermolecular 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_r = 223.23
Monoclinic, C c
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.145
S = 0.97
1278 reflections
154 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[x+2, -y, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Nitrile compounds are the precursor of tetrazole derivatives (Dunica, et al., 1991; Wittenberger, et al., 1993) and can be used for the design of noncentrosymmetric bulk materials (Xiong, et al.(2002)). We report here the crystal structure of the title compound, 4-(4-hydroxyphenylazo)benzonitrile, (I) (Fig. 1).

In I, the N=N double bond [1.257 (4) Å] is in the range found in other similar azo complexes with a trans-configuration (Harada, et al., 1997). The torsion angle C7 - N2 - N3 - C8 is -179.30 (0.32)°. The dihedral angle between the two benzene rings is 2.18 (1/5) °. The crystal structure involves O—H···N hydrogen bond resulting in the formation of a chain.

Related literature top

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 top

A solution of 4-cyanoaniline (0.71 g, 6 mmol) in a solution of hydrochloric acid (6 ml, 4M) was added to a solution of sodium nitrite (0.42 g, 6.1 mmol) in 2 ml water, and the mixture was stirred for 4 h under N2 atmosphere at 273–278 K. Then urea (0.01 g, 0.2 mmol) was added to decompose excessive nitrous acid, and the mixture was further stirred for 30 min. The solution of the diazonium salt was added to a aqueous phenol (0.62 g, 6.6 mmol), sodium carbonate (3 g), baking soda (0.2 g) and ice (15 g) at 273–278 K. The mixture was stirred for 7 h. After the reaction solution was neutralized with a solution of hydrochoric acid (13.6 ml, 3 M), the mixture was filtrated. A yellow block-like crystals (1.27 g, 5.7 mmol, 95%), which is suitable for X-ray analysis, were obtained by recrystallization from ethyl acetate (18 ml).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Hydrogen atoms not involved in hydrogen bonding (dashed lines) were omitted for clarity.

4-(4-Hydroxyphenyldiazenyl)benzonitrile top

Crystal data top

C₁₃H₉N₃O	F(000) = 464
M_r = 223.23	D_x = 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 = 3.7–27.7°
b = 10.747 (2) Å	µ = 0.09 mm⁻¹
c = 15.851 (3) Å	T = 293 K
β = 93.54 (3)°	BLOCK, yellow
V = 1110.4 (4) Å³	0.18 × 0.05 × 0.05 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	2532 independent reflections
Radiation source: fine-focus sealed tube	1296 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.7°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.781, T_max = 1	l = −20→20
5599 measured reflections

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)] = 0.053	H-atom parameters constrained
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0762P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
1278 reflections	Δρ_max = 0.17 e Å⁻³
154 parameters	Δρ_min = −0.19 e Å⁻³
2 restraints	Absolute structure: indeterminate
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₃H₉N₃O	V = 1110.4 (4) Å³
M_r = 223.23	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 6.5307 (13) Å	µ = 0.09 mm⁻¹
b = 10.747 (2) Å	T = 293 K
c = 15.851 (3) Å	0.18 × 0.05 × 0.05 mm
β = 93.54 (3)°

Data collection top

Rigaku Mercury2 diffractometer	2532 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1296 reflections with I > 2σ(I)
T_min = 0.781, T_max = 1	R_int = 0.073
5599 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	2 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 0.98	Δρ_max = 0.17 e Å⁻³
1278 reflections	Δρ_min = −0.19 e Å⁻³
154 parameters	Absolute structure: indeterminate

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+2, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉N₃O
M_r	223.23
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	6.5307 (13), 10.747 (2), 15.851 (3)
β (°)	93.54 (3)
V (Å³)	1110.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.05 × 0.05

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.781, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	5599, 2532, 1296
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.145, 0.98
No. of reflections	1278
No. of parameters	154
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19
Absolute structure	Indeterminate

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1ⁱ	0.85	2.01	2.817 (5)	159.4

Symmetry code: (i) x+2, −y, z+1/2.

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to Dr Chao Zhi Zhang.

References

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