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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049890/ww2058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049890/ww2058Isup2.hkl
Contains datablock I

CCDC reference: 630510

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

Computing details top

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 top
Crystal data top
C13H12N2OF(000) = 448
Mr = 212.25Dx = 1.276 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 11243 reflections
a = 5.6140 (5) Åθ = 2.2–27.6°
b = 17.8226 (14) ŵ = 0.08 mm1
c = 11.0657 (10) ÅT = 296 K
β = 93.720 (7)°Prism, yellow
V = 1104.86 (16) Å30.34 × 0.29 × 0.24 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
1314 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.107
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
Detector resolution: 6.67 pixels mm-1h = 77
ω scansk = 2222
13022 measured reflectionsl = 1414
2519 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0743P)2]
where P = (Fo2 + 2Fc2)/3
2519 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
xyzUiso*/Ueq
O11.6795 (2)0.82504 (10)0.61940 (15)0.0699 (5)
N21.0258 (3)0.59731 (10)0.32600 (15)0.0576 (4)
C41.1976 (3)0.66814 (12)0.47573 (18)0.0591 (4)
N11.0235 (3)0.61368 (9)0.43558 (15)0.0591 (4)
C70.8529 (3)0.54132 (12)0.28706 (18)0.0576 (4)
C31.1616 (4)0.70095 (13)0.58647 (19)0.0637 (6)
H31.03020.68700.62830.076*
C11.5174 (3)0.77388 (11)0.57532 (17)0.0540 (5)
C61.5567 (3)0.74003 (13)0.46611 (19)0.0610 (5)
H61.69200.75260.42620.073*
C51.3991 (3)0.68806 (13)0.41540 (19)0.0610 (6)
H51.42660.66630.34120.073*
C100.5300 (4)0.43407 (12)0.1916 (2)0.0650 (6)
C21.3173 (3)0.75384 (12)0.63537 (19)0.0613 (6)
H21.28870.77630.70890.074*
C120.8630 (4)0.51589 (16)0.1706 (2)0.0824 (7)
H120.97830.53500.12230.099*
C90.5194 (4)0.45993 (14)0.3078 (2)0.0759 (7)
H90.40160.44140.35520.091*
C80.6781 (4)0.51262 (13)0.3567 (2)0.0721 (6)
H80.66770.52880.43610.087*
C130.3572 (4)0.37576 (14)0.1405 (2)0.0843 (8)
H13A0.39160.36460.05860.126*
H13B0.19720.39460.14190.126*
H13C0.37260.33090.18850.126*
C110.7055 (4)0.46260 (16)0.1240 (2)0.0822 (8)
H110.71810.44560.04520.099*
H11.634 (5)0.8474 (19)0.690 (3)0.124 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0602 (8)0.0861 (12)0.0630 (10)0.0074 (8)0.0009 (7)0.0152 (9)
N20.0601 (7)0.0576 (8)0.0542 (8)0.0074 (6)0.0034 (5)0.0005 (6)
C40.0639 (7)0.0575 (8)0.0548 (8)0.0046 (6)0.0041 (6)0.0005 (6)
N10.0639 (7)0.0575 (8)0.0548 (8)0.0046 (6)0.0041 (6)0.0005 (6)
C70.0601 (7)0.0576 (8)0.0542 (8)0.0074 (6)0.0034 (5)0.0005 (6)
C30.0640 (11)0.0711 (14)0.0561 (13)0.0040 (10)0.0051 (9)0.0003 (11)
C10.0526 (10)0.0580 (12)0.0504 (11)0.0069 (9)0.0049 (8)0.0015 (9)
C60.0503 (10)0.0771 (14)0.0553 (12)0.0048 (10)0.0015 (8)0.0088 (11)
C50.0607 (11)0.0703 (14)0.0510 (12)0.0136 (10)0.0033 (9)0.0108 (10)
C100.0641 (12)0.0606 (13)0.0687 (15)0.0055 (10)0.0086 (10)0.0046 (11)
C20.0645 (12)0.0710 (14)0.0487 (12)0.0000 (10)0.0047 (9)0.0031 (10)
C120.0772 (14)0.1019 (19)0.0691 (16)0.0199 (14)0.0126 (11)0.0187 (14)
C90.0861 (15)0.0723 (15)0.0698 (16)0.0185 (12)0.0104 (12)0.0021 (12)
C80.0951 (16)0.0672 (14)0.0538 (14)0.0069 (12)0.0039 (12)0.0052 (11)
C130.0802 (15)0.0747 (16)0.095 (2)0.0090 (12)0.0140 (13)0.0140 (14)
C110.0834 (15)0.099 (2)0.0639 (15)0.0129 (14)0.0048 (12)0.0233 (14)
Geometric parameters (Å, º) top
O1—C11.356 (2)C5—H50.9300
O1—H10.93 (4)C10—C91.371 (3)
N2—N11.248 (2)C10—C111.373 (3)
N2—C71.439 (3)C10—C131.507 (3)
C4—C31.384 (3)C2—H20.9300
C4—C51.396 (3)C12—C111.375 (3)
C4—N11.428 (3)C12—H120.9300
C7—C121.371 (3)C9—C81.381 (3)
C7—C81.384 (3)C9—H90.9300
C3—C21.372 (3)C8—H80.9300
C3—H30.9300C13—H13A0.9600
C1—C61.381 (3)C13—H13B0.9600
C1—C21.389 (3)C13—H13C0.9600
C6—C51.375 (3)C11—H110.9300
C6—H60.9300
C1—O1—H1112 (2)C11—C10—C13121.2 (2)
N1—N2—C7113.80 (18)C3—C2—C1120.2 (2)
C3—C4—C5119.01 (19)C3—C2—H2119.9
C3—C4—N1115.2 (2)C1—C2—H2119.9
C5—C4—N1125.70 (19)C7—C12—C11121.1 (2)
N2—N1—C4114.28 (18)C7—C12—H12119.5
C12—C7—C8118.4 (2)C11—C12—H12119.5
C12—C7—N2116.3 (2)C10—C9—C8122.0 (2)
C8—C7—N2125.35 (19)C10—C9—H9119.0
C2—C3—C4120.9 (2)C8—C9—H9119.0
C2—C3—H3119.6C9—C8—C7119.7 (2)
C4—C3—H3119.6C9—C8—H8120.1
O1—C1—C6117.83 (19)C7—C8—H8120.1
O1—C1—C2123.06 (19)C10—C13—H13A109.5
C6—C1—C2119.11 (19)C10—C13—H13B109.5
C5—C6—C1121.1 (2)H13A—C13—H13B109.5
C5—C6—H6119.5C10—C13—H13C109.5
C1—C6—H6119.5H13A—C13—H13C109.5
C6—C5—C4119.7 (2)H13B—C13—H13C109.5
C6—C5—H5120.1C10—C11—C12121.2 (2)
C4—C5—H5120.1C10—C11—H11119.4
C9—C10—C11117.6 (2)C12—C11—H11119.4
C9—C10—C13121.2 (2)
C7—N2—N1—C4178.85 (15)O1—C1—C2—C3179.21 (18)
C3—C4—N1—N2164.55 (17)C6—C1—C2—C30.1 (3)
C5—C4—N1—N217.8 (3)C8—C7—C12—C110.7 (4)
N1—N2—C7—C12173.87 (19)N2—C7—C12—C11179.8 (2)
N1—N2—C7—C87.1 (3)C11—C10—C9—C80.1 (4)
C5—C4—C3—C21.8 (3)C13—C10—C9—C8179.2 (2)
N1—C4—C3—C2179.61 (18)C10—C9—C8—C70.7 (4)
O1—C1—C6—C5179.48 (18)C12—C7—C8—C90.2 (4)
C2—C1—C6—C51.1 (3)N2—C7—C8—C9178.7 (2)
C1—C6—C5—C41.0 (3)C9—C10—C11—C120.8 (4)
C3—C4—C5—C60.5 (3)C13—C10—C11—C12179.9 (2)
N1—C4—C5—C6178.09 (18)C7—C12—C11—C101.2 (4)
C4—C3—C2—C11.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.93 (4)1.93 (4)2.853 (2)174 (3)
Symmetry code: (i) x+1/2, y+3/2, z+1/2.
 

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