Literature DB >> 21202567

4-(4-Ethyl-phenyl-diazen-yl)phenol.

Joost de Wit, Gert O R Alberda van Ekenstein, Gerrit Ten Brinke, Auke Meetsma.   

Abstract

The crystal structure of the title compound, C(14)H(14)N(2)O, determined at 100 K, shows that the mol-ecules are not planar in the solid state, in contrast to other diazene (azobenzene) derivatives. The dihedral angle between the planes of the two aromatic rings is 42.32 (7)°. The mol-ecules are linked by inter-molecular O-H⋯N hydrogen bonds, forming an infinite one-dimensional chain.

Entities:  

Year:  2008        PMID： 21202567      PMCID： PMC2961569          DOI： 10.1107/S160053680801338X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Bowes et al. (2003 ▶); Brown et al. (1971 ▶); Burger & Ramberger (1979 ▶); Enkelmann et al. (1978 ▶); Kageyama et al. (1982 ▶, 1985 ▶, 1986 ▶); Kashino et al. (1979 ▶); Kocaokutgen et al. (2003 ▶); McWilliam et al. (2001 ▶); Okamoto et al. (1983 ▶); Okamoto & Nakano (1994 ▶); Ruokolainen et al. (1996 ▶, 1998 ▶, 1999 ▶); Shibaev et al. (2003 ▶); Soylu et al. (2004 ▶); Zhang et al. (1998 ▶).

Experimental

Crystal data

C14H14N2O M = 226.28 Monoclinic, a = 7.5261 (9) Å b = 13.4298 (15) Å c = 11.6412 (13) Å β = 97.4001 (15)° V = 1166.8 (2) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 100 (1) K 0.42 × 0.33 × 0.22 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.956, T max = 0.982 8700 measured reflections 2276 independent reflections 1848 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.107 S = 1.04 2276 reflections 210 parameters All H-atom parameters refined Δρmax = 0.17 e Å−3 Δρmin = −0.24 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and PLUTO (Meetsma, 2007 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801338X/bg2174sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680801338X/bg2174Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H14N2OF000 = 480
Mr = 226.28Dx = 1.288 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3059 reflections
a = 7.5261 (9) Åθ = 3.0–27.5º
b = 13.4298 (15) ŵ = 0.08 mm−1
c = 11.6412 (13) ÅT = 100 (1) K
β = 97.4001 (15)ºBlock, orange
V = 1166.8 (2) Å30.42 × 0.33 × 0.22 mm
Z = 4
Bruker SMART APEX CCD area-detector diffractometer2276 independent reflections
Monochromator: parallel mounted graphite1848 reflections with I > 2σ(I)
Detector resolution: 66.06 pixels mm-1Rint = 0.028
T = 100(1) Kθmax = 26.0º
φ and ω scansθmin = 3.0º
Absorption correction: multi-scan(SADABS; Bruker, 2007)h = −9→9
Tmin = 0.956, Tmax = 0.982k = −16→15
8700 measured reflectionsl = −14→14
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.107  w = 1/[σ2(Fo2) + (0.0608P)2 + 0.2293P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2276 reflectionsΔρmax = 0.17 e Å−3
210 parametersΔρmin = −0.24 e Å−3
Primary atom site location: heavy-atom methodExtinction correction: none
Experimental. The final unit cell was obtained from the xyz centroids of 3059 reflections after integration using the SAINTPLUS software package (Bruker, 2007).Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
O11.04406 (14)0.48064 (7)0.32923 (9)0.0263 (3)
N10.80788 (15)0.08833 (8)0.34477 (9)0.0188 (3)
N20.75956 (15)0.06025 (8)0.43960 (10)0.0199 (3)
C10.98453 (18)0.38503 (10)0.32795 (11)0.0193 (4)
C20.99777 (18)0.31861 (10)0.23708 (12)0.0201 (4)
C30.93839 (18)0.22132 (10)0.24543 (12)0.0190 (4)
C40.86411 (17)0.18959 (10)0.34290 (11)0.0175 (4)
C50.84621 (18)0.25739 (10)0.43237 (12)0.0190 (4)
C60.90547 (18)0.35397 (10)0.42467 (12)0.0204 (4)
C70.69280 (17)−0.03918 (10)0.43646 (12)0.0190 (4)
C80.59745 (19)−0.08196 (11)0.33765 (12)0.0223 (4)
C90.53750 (19)−0.17915 (11)0.34156 (13)0.0232 (4)
C100.57357 (18)−0.23637 (10)0.44256 (12)0.0214 (4)
C110.66447 (19)−0.19152 (11)0.54092 (13)0.0228 (4)
C120.72082 (19)−0.09323 (11)0.53944 (12)0.0216 (4)
C130.5212 (2)−0.34494 (11)0.44295 (14)0.0260 (5)
C140.6554 (2)−0.41051 (12)0.39094 (16)0.0298 (5)
H11.096 (3)0.4963 (14)0.2651 (19)0.054 (6)*
H21.0497 (19)0.3401 (11)0.1707 (13)0.025 (4)*
H30.9523 (19)0.1728 (11)0.1835 (13)0.022 (4)*
H50.7933 (19)0.2348 (10)0.4993 (13)0.019 (4)*
H60.894 (2)0.4036 (11)0.4876 (13)0.023 (4)*
H80.569 (2)−0.0420 (12)0.2682 (14)0.026 (4)*
H90.472 (2)−0.2076 (11)0.2751 (14)0.025 (4)*
H110.690 (2)−0.2308 (11)0.6131 (13)0.023 (4)*
H120.781 (2)−0.0609 (11)0.6080 (14)0.027 (4)*
H130.515 (2)−0.3675 (13)0.5252 (16)0.043 (5)*
H13'0.401 (2)−0.3550 (12)0.3973 (15)0.038 (5)*
H140.779 (3)−0.4016 (13)0.4330 (16)0.047 (5)*
H14'0.662 (2)−0.3941 (13)0.3112 (17)0.041 (5)*
H14"0.624 (2)−0.4825 (13)0.3936 (15)0.038 (5)*
U11U22U33U12U13U23
O10.0395 (6)0.0160 (5)0.0260 (6)−0.0050 (4)0.0138 (5)−0.0013 (4)
N10.0182 (6)0.0180 (6)0.0204 (6)0.0009 (4)0.0032 (5)0.0016 (5)
N20.0207 (6)0.0169 (6)0.0224 (6)0.0011 (4)0.0042 (5)0.0009 (5)
C10.0215 (7)0.0149 (7)0.0211 (7)0.0007 (5)0.0017 (5)0.0019 (5)
C20.0220 (7)0.0201 (7)0.0186 (7)0.0004 (5)0.0046 (5)0.0025 (6)
C30.0197 (7)0.0176 (7)0.0195 (7)0.0015 (5)0.0020 (5)−0.0015 (6)
C40.0173 (7)0.0148 (7)0.0202 (7)0.0009 (5)0.0017 (5)0.0000 (5)
C50.0196 (7)0.0195 (7)0.0184 (7)0.0020 (5)0.0042 (5)0.0022 (5)
C60.0241 (7)0.0175 (7)0.0201 (7)0.0018 (5)0.0044 (6)−0.0026 (5)
C70.0180 (7)0.0155 (7)0.0244 (7)0.0017 (5)0.0067 (5)−0.0003 (5)
C80.0214 (7)0.0216 (8)0.0240 (7)0.0006 (6)0.0037 (6)0.0038 (6)
C90.0212 (7)0.0235 (8)0.0248 (8)−0.0027 (6)0.0029 (6)−0.0026 (6)
C100.0173 (7)0.0185 (7)0.0298 (8)−0.0005 (5)0.0082 (6)−0.0005 (6)
C110.0231 (7)0.0205 (8)0.0253 (8)0.0012 (6)0.0048 (6)0.0059 (6)
C120.0220 (8)0.0219 (8)0.0210 (7)−0.0004 (6)0.0034 (6)−0.0001 (6)
C130.0258 (8)0.0192 (8)0.0341 (9)−0.0036 (6)0.0078 (7)0.0008 (6)
C140.0288 (9)0.0209 (8)0.0398 (10)−0.0010 (6)0.0044 (7)−0.0051 (7)
O1—C11.3594 (17)C10—C131.511 (2)
O1—H10.91 (2)C11—C121.387 (2)
N1—N21.2636 (16)C13—C141.523 (2)
N1—C41.4252 (17)C2—H20.954 (15)
N2—C71.4255 (17)C3—H30.987 (15)
C1—C61.4030 (19)C5—H50.968 (15)
C1—C21.3971 (19)C6—H61.002 (15)
C2—C31.3884 (19)C8—H80.971 (16)
C3—C41.3946 (19)C9—H90.943 (16)
C4—C51.4029 (19)C11—H110.990 (15)
C5—C61.3783 (19)C12—H120.968 (16)
C7—C81.398 (2)C13—H131.011 (18)
C7—C121.394 (2)C13—H13'0.998 (16)
C8—C91.384 (2)C14—H141.00 (2)
C9—C101.402 (2)C14—H14'0.96 (2)
C10—C111.393 (2)C14—H14"0.997 (17)
O1···N1i2.8316 (15)C8···H2iii2.868 (15)
O1···C3i3.3541 (17)C9···H14'3.069 (17)
O1···H3i2.585 (15)C10···H5v2.926 (15)
O1···H6ii2.632 (15)C13···H5v2.942 (14)
N1···O1iii2.8316 (15)C14···H8x2.932 (16)
N1···H82.584 (16)H1···N1i1.98 (2)
N1···H1iii1.98 (2)H1···N2i2.88 (2)
N2···H52.449 (14)H1···C3i3.034 (19)
N2···H1iii2.88 (2)H1···C4i2.92 (2)
C2···C8i3.536 (2)H1···C7i3.04 (2)
C3···O1iii3.3541 (17)H1···C8i2.93 (2)
C4···C12iv3.494 (2)H2···C7i2.926 (15)
C5···C13v3.488 (2)H2···C8i2.868 (15)
C7···C7v3.5810 (19)H3···O1iii2.585 (15)
C8···C2iii3.536 (2)H3···C5vi3.076 (15)
C12···C4iv3.494 (2)H3···C6vi3.010 (15)
C13···C5v3.488 (2)H5···N22.449 (14)
C2···H5vi3.074 (15)H5···C10v2.926 (15)
C2···H11iv2.983 (15)H5···C13v2.942 (14)
C3···H13'vii3.040 (16)H5···C2viii3.074 (15)
C3···H11iv3.060 (15)H5···C3viii2.991 (15)
C3···H5vi2.991 (15)H6···O1ii2.632 (15)
C3···H1iii3.034 (19)H8···N12.584 (16)
C4···H1iii2.92 (2)H8···C14vii2.932 (16)
C4···H9vii3.049 (15)H9···C4x3.049 (15)
C5···H3viii3.076 (15)H11···C2iv2.983 (15)
C6···H14iv2.79 (2)H11···C3iv3.060 (15)
C6···H3viii3.010 (15)H13'···C3x3.040 (16)
C6···H14"ix3.040 (17)H14···C6iv2.79 (2)
C7···H2iii2.926 (15)H14'···C93.069 (17)
C7···H1iii3.04 (2)H14"···C6xi3.040 (17)
C8···H1iii2.93 (2)
C1—O1—H1112.6 (12)C2—C3—H3120.3 (9)
N2—N1—C4114.68 (10)C4—C3—H3118.9 (9)
N1—N2—C7113.41 (11)C4—C5—H5118.9 (8)
O1—C1—C6116.44 (12)C6—C5—H5121.2 (8)
C2—C1—C6119.79 (12)C1—C6—H6118.3 (9)
O1—C1—C2123.77 (12)C5—C6—H6121.3 (9)
C1—C2—C3119.53 (13)C7—C8—H8119.5 (10)
C2—C3—C4120.72 (13)C9—C8—H8120.7 (9)
N1—C4—C3117.06 (11)C8—C9—H9119.6 (9)
C3—C4—C5119.51 (12)C10—C9—H9119.4 (9)
N1—C4—C5123.43 (12)C10—C11—H11119.2 (9)
C4—C5—C6119.98 (13)C12—C11—H11119.4 (9)
C1—C6—C5120.41 (13)C7—C12—H12118.6 (9)
N2—C7—C8123.21 (12)C11—C12—H12121.9 (9)
C8—C7—C12119.88 (13)C10—C13—H13109.6 (10)
N2—C7—C12116.87 (12)C10—C13—H13'110.4 (9)
C7—C8—C9119.70 (13)C14—C13—H13108.5 (9)
C8—C9—C10121.07 (13)C14—C13—H13'108.2 (10)
C9—C10—C13120.62 (13)H13—C13—H13'108.3 (13)
C11—C10—C13121.04 (13)C13—C14—H14111.0 (11)
C9—C10—C11118.30 (13)C13—C14—H14'111.8 (10)
C10—C11—C12121.32 (13)C13—C14—H14"112.1 (9)
C7—C12—C11119.57 (13)H14—C14—H14'106.5 (14)
C10—C13—C14111.73 (12)H14—C14—H14"108.1 (14)
C1—C2—H2119.8 (9)H14'—C14—H14"107.1 (14)
C3—C2—H2120.7 (9)
C4—N1—N2—C7176.04 (11)C4—C5—C6—C1−0.3 (2)
N2—N1—C4—C3172.74 (12)N2—C7—C8—C9179.83 (13)
N2—N1—C4—C5−8.05 (18)C12—C7—C8—C9−2.5 (2)
N1—N2—C7—C8−33.70 (18)N2—C7—C12—C11−177.78 (13)
N1—N2—C7—C12148.57 (12)C8—C7—C12—C114.4 (2)
O1—C1—C2—C3177.87 (13)C7—C8—C9—C10−1.2 (2)
C6—C1—C2—C3−2.4 (2)C8—C9—C10—C112.9 (2)
O1—C1—C6—C5−178.04 (12)C8—C9—C10—C13−174.80 (13)
C2—C1—C6—C52.2 (2)C9—C10—C11—C12−1.0 (2)
C1—C2—C3—C40.7 (2)C13—C10—C11—C12176.74 (13)
C2—C3—C4—N1−179.53 (12)C9—C10—C13—C1480.03 (17)
C2—C3—C4—C51.2 (2)C11—C10—C13—C14−97.60 (17)
N1—C4—C5—C6179.38 (12)C10—C11—C12—C7−2.7 (2)
C3—C4—C5—C6−1.4 (2)
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.91 (2)1.98 (2)2.8316 (15)154.7 (17)
C3—H3···O1iii0.987 (15)2.585 (15)3.3541 (17)134.7 (11)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯N1i0.91 (2)1.98 (2)2.8316 (15)154.7 (17)
C3—H3⋯O1ii0.987 (15)2.585 (15)3.3541 (17)134.7 (11)

Symmetry codes: (i) ; (ii) .

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