(E)-4-(p-Tolyl­diazen­yl)phenol

The title compound, C₁₃H₁₂N₂O, consisting of two aromatic groups linked through a diazene bridge, exhibits trans geometry with respect to the azo double bond and deviates slightly from planarity. The crystal structure is stabilized by inter­molecular O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.160
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.106
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C13

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-4-(p-Tolyldiazenyl}phenol

Crystal data

C13H12N2O	F(000) = 448
Mr = 212.25	Dx = 1.276 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11243 reflections
a = 5.6140 (5) Å	θ = 2.2–27.6°
b = 17.8226 (14) Å	µ = 0.08 mm^−1
c = 11.0657 (10) Å	T = 296 K
β = 93.720 (7)°	Prism, yellow
V = 1104.86 (16) Å^3	0.34 × 0.29 × 0.24 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	1314 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.107
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
Detector resolution: 6.67 pixels mm^-1	h = −7→7
ω scans	k = −22→22
13022 measured reflections	l = −14→14
2519 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0743P)^2] where P = (Fo^2 + 2Fc^2)/3
2519 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	1.6795 (2)	0.82504 (10)	0.61940 (15)	0.0699 (5)
N2	1.0258 (3)	0.59731 (10)	0.32600 (15)	0.0576 (4)
C4	1.1976 (3)	0.66814 (12)	0.47573 (18)	0.0591 (4)
N1	1.0235 (3)	0.61368 (9)	0.43558 (15)	0.0591 (4)
C7	0.8529 (3)	0.54132 (12)	0.28706 (18)	0.0576 (4)
C3	1.1616 (4)	0.70095 (13)	0.58647 (19)	0.0637 (6)
H3	1.0302	0.6870	0.6283	0.076*
C1	1.5174 (3)	0.77388 (11)	0.57532 (17)	0.0540 (5)
C6	1.5567 (3)	0.74003 (13)	0.46611 (19)	0.0610 (5)
H6	1.6920	0.7526	0.4262	0.073*
C5	1.3991 (3)	0.68806 (13)	0.41540 (19)	0.0610 (6)
H5	1.4266	0.6663	0.3412	0.073*
C10	0.5300 (4)	0.43407 (12)	0.1916 (2)	0.0650 (6)
C2	1.3173 (3)	0.75384 (12)	0.63537 (19)	0.0613 (6)
H2	1.2887	0.7763	0.7089	0.074*
C12	0.8630 (4)	0.51589 (16)	0.1706 (2)	0.0824 (7)
H12	0.9783	0.5350	0.1223	0.099*
C9	0.5194 (4)	0.45993 (14)	0.3078 (2)	0.0759 (7)
H9	0.4016	0.4414	0.3552	0.091*
C8	0.6781 (4)	0.51262 (13)	0.3567 (2)	0.0721 (6)
H8	0.6677	0.5288	0.4361	0.087*
C13	0.3572 (4)	0.37576 (14)	0.1405 (2)	0.0843 (8)
H13A	0.3916	0.3646	0.0586	0.126*
H13B	0.1972	0.3946	0.1419	0.126*
H13C	0.3726	0.3309	0.1885	0.126*
C11	0.7055 (4)	0.46260 (16)	0.1240 (2)	0.0822 (8)
H11	0.7181	0.4456	0.0452	0.099*
H1	1.634 (5)	0.8474 (19)	0.690 (3)	0.124 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0602 (8)	0.0861 (12)	0.0630 (10)	−0.0074 (8)	0.0009 (7)	−0.0152 (9)
N2	0.0601 (7)	0.0576 (8)	0.0542 (8)	0.0074 (6)	−0.0034 (5)	−0.0005 (6)
C4	0.0639 (7)	0.0575 (8)	0.0548 (8)	0.0046 (6)	−0.0041 (6)	−0.0005 (6)
N1	0.0639 (7)	0.0575 (8)	0.0548 (8)	0.0046 (6)	−0.0041 (6)	−0.0005 (6)
C7	0.0601 (7)	0.0576 (8)	0.0542 (8)	0.0074 (6)	−0.0034 (5)	−0.0005 (6)
C3	0.0640 (11)	0.0711 (14)	0.0561 (13)	−0.0040 (10)	0.0051 (9)	0.0003 (11)
C1	0.0526 (10)	0.0580 (12)	0.0504 (11)	0.0069 (9)	−0.0049 (8)	−0.0015 (9)
C6	0.0503 (10)	0.0771 (14)	0.0553 (12)	0.0048 (10)	0.0015 (8)	−0.0088 (11)
C5	0.0607 (11)	0.0703 (14)	0.0510 (12)	0.0136 (10)	−0.0033 (9)	−0.0108 (10)
C10	0.0641 (12)	0.0606 (13)	0.0687 (15)	0.0055 (10)	−0.0086 (10)	−0.0046 (11)
C2	0.0645 (12)	0.0710 (14)	0.0487 (12)	0.0000 (10)	0.0047 (9)	−0.0031 (10)
C12	0.0772 (14)	0.1019 (19)	0.0691 (16)	−0.0199 (14)	0.0126 (11)	−0.0187 (14)
C9	0.0861 (15)	0.0723 (15)	0.0698 (16)	−0.0185 (12)	0.0104 (12)	−0.0021 (12)
C8	0.0951 (16)	0.0672 (14)	0.0538 (14)	−0.0069 (12)	0.0039 (12)	−0.0052 (11)
C13	0.0802 (15)	0.0747 (16)	0.095 (2)	−0.0090 (12)	−0.0140 (13)	−0.0140 (14)
C11	0.0834 (15)	0.099 (2)	0.0639 (15)	−0.0129 (14)	0.0048 (12)	−0.0233 (14)

Geometric parameters (Å, º)

O1—C1	1.356 (2)	C5—H5	0.9300
O1—H1	0.93 (4)	C10—C9	1.371 (3)
N2—N1	1.248 (2)	C10—C11	1.373 (3)
N2—C7	1.439 (3)	C10—C13	1.507 (3)
C4—C3	1.384 (3)	C2—H2	0.9300
C4—C5	1.396 (3)	C12—C11	1.375 (3)
C4—N1	1.428 (3)	C12—H12	0.9300
C7—C12	1.371 (3)	C9—C8	1.381 (3)
C7—C8	1.384 (3)	C9—H9	0.9300
C3—C2	1.372 (3)	C8—H8	0.9300
C3—H3	0.9300	C13—H13A	0.9600
C1—C6	1.381 (3)	C13—H13B	0.9600
C1—C2	1.389 (3)	C13—H13C	0.9600
C6—C5	1.375 (3)	C11—H11	0.9300
C6—H6	0.9300
C1—O1—H1	112 (2)	C11—C10—C13	121.2 (2)
N1—N2—C7	113.80 (18)	C3—C2—C1	120.2 (2)
C3—C4—C5	119.01 (19)	C3—C2—H2	119.9
C3—C4—N1	115.2 (2)	C1—C2—H2	119.9
C5—C4—N1	125.70 (19)	C7—C12—C11	121.1 (2)
N2—N1—C4	114.28 (18)	C7—C12—H12	119.5
C12—C7—C8	118.4 (2)	C11—C12—H12	119.5
C12—C7—N2	116.3 (2)	C10—C9—C8	122.0 (2)
C8—C7—N2	125.35 (19)	C10—C9—H9	119.0
C2—C3—C4	120.9 (2)	C8—C9—H9	119.0
C2—C3—H3	119.6	C9—C8—C7	119.7 (2)
C4—C3—H3	119.6	C9—C8—H8	120.1
O1—C1—C6	117.83 (19)	C7—C8—H8	120.1
O1—C1—C2	123.06 (19)	C10—C13—H13A	109.5
C6—C1—C2	119.11 (19)	C10—C13—H13B	109.5
C5—C6—C1	121.1 (2)	H13A—C13—H13B	109.5
C5—C6—H6	119.5	C10—C13—H13C	109.5
C1—C6—H6	119.5	H13A—C13—H13C	109.5
C6—C5—C4	119.7 (2)	H13B—C13—H13C	109.5
C6—C5—H5	120.1	C10—C11—C12	121.2 (2)
C4—C5—H5	120.1	C10—C11—H11	119.4
C9—C10—C11	117.6 (2)	C12—C11—H11	119.4
C9—C10—C13	121.2 (2)
C7—N2—N1—C4	178.85 (15)	O1—C1—C2—C3	−179.21 (18)
C3—C4—N1—N2	164.55 (17)	C6—C1—C2—C3	0.1 (3)
C5—C4—N1—N2	−17.8 (3)	C8—C7—C12—C11	−0.7 (4)
N1—N2—C7—C12	−173.87 (19)	N2—C7—C12—C11	−179.8 (2)
N1—N2—C7—C8	7.1 (3)	C11—C10—C9—C8	−0.1 (4)
C5—C4—C3—C2	1.8 (3)	C13—C10—C9—C8	179.2 (2)
N1—C4—C3—C2	179.61 (18)	C10—C9—C8—C7	0.7 (4)
O1—C1—C6—C5	−179.48 (18)	C12—C7—C8—C9	−0.2 (4)
C2—C1—C6—C5	1.1 (3)	N2—C7—C8—C9	178.7 (2)
C1—C6—C5—C4	−1.0 (3)	C9—C10—C11—C12	−0.8 (4)
C3—C4—C5—C6	−0.5 (3)	C13—C10—C11—C12	179.9 (2)
N1—C4—C5—C6	−178.09 (18)	C7—C12—C11—C10	1.2 (4)
C4—C3—C2—C1	−1.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2^i	0.93 (4)	1.93 (4)	2.853 (2)	174 (3)

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.