4-(4-Ethyl­phenyl­diazen­yl)phenol

Wit, J. de; Alberda van Ekenstein, G.O.R.; Brinke, G. ten; Meetsma, A.

doi:10.1107/S160053680801338X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1048

doi:10.1107/S160053680801338X

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4-(4-Ethylphenyldiazenyl)phenol

Joost de Wit,^a Gert O. R. Alberda van Ekenstein,^a Gerrit ten Brinke ^a and Auke Meetsma ^b ^*

^aLaboratory of Polymer Chemistry, Zernike Institute for Advanced Materials, University of Groningen, NL-9747 AG Groningen, The Netherlands, and ^bCrystal Structure Center, Chemical Physics, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands
^*Correspondence e-mail: a.meetsma@rug.nl

(Received 26 March 2008; accepted 6 May 2008; online 10 May 2008)

The crystal structure of the title compound, C₁₄H₁₄N₂O, determined at 100 K, shows that the molecules 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 molecules are linked by intermolecular O—H⋯N hydrogen bonds, forming an infinite one-dimensional chain.

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_r = 226.28
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.04
2276 reflections
210 parameters
All H-atom parameters refined
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.91 (2)	1.98 (2)	2.8316 (15)	154.7 (17)
C3—H3⋯O1ⁱⁱ	0.987 (15)	2.585 (15)	3.3541 (17)	134.7 (11)
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801338X/bg2174sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801338X/bg2174Isup2.hkl

checkCIF report

Comment top

Azobenzenes are widely used as dyes, but also as photochemical switch using photo-isomerization by UV light to induce a conformational change from trans to cis and back. This principle has been explored extensively in order to exploit the isomerization for several applications. (Shibaev et al., 2003) The presence of the phenolic moiety makes it possible to form complexes with e.g. poly (4-vinylpyridine) homopolymer or with poly (4-vinylpyridine) containing block copolymers. These supramolecular comb-like polymeric structures give rise to hierarchical structure-in-structure morphologies comparable with the systems with poly (4-vinylpyridine) containing block co-polymers complexed with nona- or pentadecylphenol. (Ruokolainen et al., 1998, 1999) The molecular geometry of (I) and the adopted atom-numbering scheme are shown in the perspective view in Figure 1. The crystal structure is similar to several other azo compounds, (Kocaokutgen et al. 2003; Soylu et al. 2004; Zhang et al., 1998) The –N1=N2- bond length is 1.2636 (16) Å, indicating a double-bond character. Regarding the azo double bond the rings are in a trans configuration. In contrast to many other azocompounds the benzene rings of EPAP are not coplanar.

Related literature top

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 top

To a vigorously stirred solution of 1.21 g of ethylaniline (0.01 mol) in 3 ml of water and 3 ml of concentrated hydrochloric acid, a solution of 2.8 g sodiumnitrite in 20 ml water was added drop wise while maintaining the temperature during the reaction at 0 °C. The resulting pale yellow mixture was added drop wise to a phenolate ion solution which was prepared by dissolving 0.94 g phenol (0.01 mol) and 0.84 g potassium hydroxide (0.015 mol) in 20 ml of methanol. Dichloromethane was used to extract the product from the aquatic reaction mixture, followed by 5 times washing with water. The solvent was then removed by evaporation. Subsequently the crude product was purified over a silica gel column using a dichloromethane / n-hexane mixture (3:1 v/v). The final solution was evaporated to dryness and dried further overnight in vacuum at 40°C. The yield of the bright orange crystalline solid was 61%. Single crystals of (I) suitable for the x-ray analysis were grown by slow evaporation from a dichloromethane solution at room temperature in air.

Analysis Differential Scanning Calorimetry (DSC, Q1000 TA instruments; 10°C/min): melting point (onset) 120°C. H-NMR (Varian VXR 300 MHz, CDCl₃): δ p.p.m. = 7.85 (d, 2H, H-3 and H-5), 7.79 p.p.m. (d, 2H, H-3' and H-5'), 7.31 p.p.m. (d, 2H, H-2' and H-6'), 6.92 p.p.m. (d, 2H, H-2 and H-6), 5.09 p.p.m. (s, 1H, –OH), 2.67 p.p.m. (t, 2H, H_A), 1.57 p.p.m. (m, 2H, –CH2-)), 1.26 p.p.m. (t, 3H, CH₃—CH₂). Mass (Jeol JMS 600H EI+ 70 eV): m/z = 226 (calculated: 226.3)

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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 (Spek, 2003).

Figures top

	Fig. 1. Perspective ORTEP drawing of (I) with the atom-labeling scheme of the non-hydrogen atoms. All atoms are represented by their displacement ellipsoids drawn at 50% probability level.
	Fig. 2. Crystal packing view of (I), showing the hydrogen bonds as dashed lines. Symmetry codes, as in Table 1.

4-(4-Ethylphenyldiazenyl)phenol top

Crystal data top

C₁₄H₁₄N₂O	F(000) = 480
M_r = 226.28	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3059 reflections
a = 7.5261 (9) Å	θ = 3.0–27.5°
b = 13.4298 (15) Å	µ = 0.08 mm⁻¹
c = 11.6412 (13) Å	T = 100 K
β = 97.4001 (15)°	Block, orange
V = 1166.8 (2) Å³	0.42 × 0.33 × 0.22 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2276 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1848 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	R_int = 0.028
Detector resolution: 66.06 pixels mm^-1	θ_max = 26.0°, θ_min = 3.0°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −16→15
T_min = 0.956, T_max = 0.982	l = −14→14
8700 measured reflections

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.107	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0608P)² + 0.2293P] where P = (F_o² + 2F_c²)/3
2276 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O	V = 1166.8 (2) Å³
M_r = 226.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5261 (9) Å	µ = 0.08 mm⁻¹
b = 13.4298 (15) Å	T = 100 K
c = 11.6412 (13) Å	0.42 × 0.33 × 0.22 mm
β = 97.4001 (15)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2276 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1848 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.982	R_int = 0.028
8700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	All H-atom parameters refined
S = 1.04	Δρ_max = 0.17 e Å⁻³
2276 reflections	Δρ_min = −0.24 e Å⁻³
210 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	1.04406 (14)	0.48064 (7)	0.32923 (9)	0.0263 (3)
N1	0.80788 (15)	0.08833 (8)	0.34477 (9)	0.0188 (3)
N2	0.75956 (15)	0.06025 (8)	0.43960 (10)	0.0199 (3)
C1	0.98453 (18)	0.38503 (10)	0.32795 (11)	0.0193 (4)
C2	0.99777 (18)	0.31861 (10)	0.23708 (12)	0.0201 (4)
C3	0.93839 (18)	0.22132 (10)	0.24543 (12)	0.0190 (4)
C4	0.86411 (17)	0.18959 (10)	0.34290 (11)	0.0175 (4)
C5	0.84621 (18)	0.25739 (10)	0.43237 (12)	0.0190 (4)
C6	0.90547 (18)	0.35397 (10)	0.42467 (12)	0.0204 (4)
C7	0.69280 (17)	−0.03918 (10)	0.43646 (12)	0.0190 (4)
C8	0.59745 (19)	−0.08196 (11)	0.33765 (12)	0.0223 (4)
C9	0.53750 (19)	−0.17915 (11)	0.34156 (13)	0.0232 (4)
C10	0.57357 (18)	−0.23637 (10)	0.44256 (12)	0.0214 (4)
C11	0.66447 (19)	−0.19152 (11)	0.54092 (13)	0.0228 (4)
C12	0.72082 (19)	−0.09323 (11)	0.53944 (12)	0.0216 (4)
C13	0.5212 (2)	−0.34494 (11)	0.44295 (14)	0.0260 (5)
C14	0.6554 (2)	−0.41051 (12)	0.39094 (16)	0.0298 (5)
H1	1.096 (3)	0.4963 (14)	0.2651 (19)	0.054 (6)*
H2	1.0497 (19)	0.3401 (11)	0.1707 (13)	0.025 (4)*
H3	0.9523 (19)	0.1728 (11)	0.1835 (13)	0.022 (4)*
H5	0.7933 (19)	0.2348 (10)	0.4993 (13)	0.019 (4)*
H6	0.894 (2)	0.4036 (11)	0.4876 (13)	0.023 (4)*
H8	0.569 (2)	−0.0420 (12)	0.2682 (14)	0.026 (4)*
H9	0.472 (2)	−0.2076 (11)	0.2751 (14)	0.025 (4)*
H11	0.690 (2)	−0.2308 (11)	0.6131 (13)	0.023 (4)*
H12	0.781 (2)	−0.0609 (11)	0.6080 (14)	0.027 (4)*
H13	0.515 (2)	−0.3675 (13)	0.5252 (16)	0.043 (5)*
H13'	0.401 (2)	−0.3550 (12)	0.3973 (15)	0.038 (5)*
H14	0.779 (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)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0395 (6)	0.0160 (5)	0.0260 (6)	−0.0050 (4)	0.0138 (5)	−0.0013 (4)
N1	0.0182 (6)	0.0180 (6)	0.0204 (6)	0.0009 (4)	0.0032 (5)	0.0016 (5)
N2	0.0207 (6)	0.0169 (6)	0.0224 (6)	0.0011 (4)	0.0042 (5)	0.0009 (5)
C1	0.0215 (7)	0.0149 (7)	0.0211 (7)	0.0007 (5)	0.0017 (5)	0.0019 (5)
C2	0.0220 (7)	0.0201 (7)	0.0186 (7)	0.0004 (5)	0.0046 (5)	0.0025 (6)
C3	0.0197 (7)	0.0176 (7)	0.0195 (7)	0.0015 (5)	0.0020 (5)	−0.0015 (6)
C4	0.0173 (7)	0.0148 (7)	0.0202 (7)	0.0009 (5)	0.0017 (5)	0.0000 (5)
C5	0.0196 (7)	0.0195 (7)	0.0184 (7)	0.0020 (5)	0.0042 (5)	0.0022 (5)
C6	0.0241 (7)	0.0175 (7)	0.0201 (7)	0.0018 (5)	0.0044 (6)	−0.0026 (5)
C7	0.0180 (7)	0.0155 (7)	0.0244 (7)	0.0017 (5)	0.0067 (5)	−0.0003 (5)
C8	0.0214 (7)	0.0216 (8)	0.0240 (7)	0.0006 (6)	0.0037 (6)	0.0038 (6)
C9	0.0212 (7)	0.0235 (8)	0.0248 (8)	−0.0027 (6)	0.0029 (6)	−0.0026 (6)
C10	0.0173 (7)	0.0185 (7)	0.0298 (8)	−0.0005 (5)	0.0082 (6)	−0.0005 (6)
C11	0.0231 (7)	0.0205 (8)	0.0253 (8)	0.0012 (6)	0.0048 (6)	0.0059 (6)
C12	0.0220 (8)	0.0219 (8)	0.0210 (7)	−0.0004 (6)	0.0034 (6)	−0.0001 (6)
C13	0.0258 (8)	0.0192 (8)	0.0341 (9)	−0.0036 (6)	0.0078 (7)	0.0008 (6)
C14	0.0288 (9)	0.0209 (8)	0.0398 (10)	−0.0010 (6)	0.0044 (7)	−0.0051 (7)

Geometric parameters (Å, º) top

O1—C1	1.3594 (17)	C10—C13	1.511 (2)
O1—H1	0.91 (2)	C11—C12	1.387 (2)
N1—N2	1.2636 (16)	C13—C14	1.523 (2)
N1—C4	1.4252 (17)	C2—H2	0.954 (15)
N2—C7	1.4255 (17)	C3—H3	0.987 (15)
C1—C6	1.4030 (19)	C5—H5	0.968 (15)
C1—C2	1.3971 (19)	C6—H6	1.002 (15)
C2—C3	1.3884 (19)	C8—H8	0.971 (16)
C3—C4	1.3946 (19)	C9—H9	0.943 (16)
C4—C5	1.4029 (19)	C11—H11	0.990 (15)
C5—C6	1.3783 (19)	C12—H12	0.968 (16)
C7—C8	1.398 (2)	C13—H13	1.011 (18)
C7—C12	1.394 (2)	C13—H13'	0.998 (16)
C8—C9	1.384 (2)	C14—H14	1.00 (2)
C9—C10	1.402 (2)	C14—H14'	0.96 (2)
C10—C11	1.393 (2)	C14—H14"	0.997 (17)

O1···N1ⁱ	2.8316 (15)	C8···H2ⁱⁱⁱ	2.868 (15)
O1···C3ⁱ	3.3541 (17)	C9···H14'	3.069 (17)
O1···H3ⁱ	2.585 (15)	C10···H5^v	2.926 (15)
O1···H6ⁱⁱ	2.632 (15)	C13···H5^v	2.942 (14)
N1···O1ⁱⁱⁱ	2.8316 (15)	C14···H8^x	2.932 (16)
N1···H8	2.584 (16)	H1···N1ⁱ	1.98 (2)
N1···H1ⁱⁱⁱ	1.98 (2)	H1···N2ⁱ	2.88 (2)
N2···H5	2.449 (14)	H1···C3ⁱ	3.034 (19)
N2···H1ⁱⁱⁱ	2.88 (2)	H1···C4ⁱ	2.92 (2)
C2···C8ⁱ	3.536 (2)	H1···C7ⁱ	3.04 (2)
C3···O1ⁱⁱⁱ	3.3541 (17)	H1···C8ⁱ	2.93 (2)
C4···C12^iv	3.494 (2)	H2···C7ⁱ	2.926 (15)
C5···C13^v	3.488 (2)	H2···C8ⁱ	2.868 (15)
C7···C7^v	3.5810 (19)	H3···O1ⁱⁱⁱ	2.585 (15)
C8···C2ⁱⁱⁱ	3.536 (2)	H3···C5^vi	3.076 (15)
C12···C4^iv	3.494 (2)	H3···C6^vi	3.010 (15)
C13···C5^v	3.488 (2)	H5···N2	2.449 (14)
C2···H5^vi	3.074 (15)	H5···C10^v	2.926 (15)
C2···H11^iv	2.983 (15)	H5···C13^v	2.942 (14)
C3···H13'^vii	3.040 (16)	H5···C2^viii	3.074 (15)
C3···H11^iv	3.060 (15)	H5···C3^viii	2.991 (15)
C3···H5^vi	2.991 (15)	H6···O1ⁱⁱ	2.632 (15)
C3···H1ⁱⁱⁱ	3.034 (19)	H8···N1	2.584 (16)
C4···H1ⁱⁱⁱ	2.92 (2)	H8···C14^vii	2.932 (16)
C4···H9^vii	3.049 (15)	H9···C4^x	3.049 (15)
C5···H3^viii	3.076 (15)	H11···C2^iv	2.983 (15)
C6···H14^iv	2.79 (2)	H11···C3^iv	3.060 (15)
C6···H3^viii	3.010 (15)	H13'···C3^x	3.040 (16)
C6···H14"^ix	3.040 (17)	H14···C6^iv	2.79 (2)
C7···H2ⁱⁱⁱ	2.926 (15)	H14'···C9	3.069 (17)
C7···H1ⁱⁱⁱ	3.04 (2)	H14"···C6^xi	3.040 (17)
C8···H1ⁱⁱⁱ	2.93 (2)

C1—O1—H1	112.6 (12)	C2—C3—H3	120.3 (9)
N2—N1—C4	114.68 (10)	C4—C3—H3	118.9 (9)
N1—N2—C7	113.41 (11)	C4—C5—H5	118.9 (8)
O1—C1—C6	116.44 (12)	C6—C5—H5	121.2 (8)
C2—C1—C6	119.79 (12)	C1—C6—H6	118.3 (9)
O1—C1—C2	123.77 (12)	C5—C6—H6	121.3 (9)
C1—C2—C3	119.53 (13)	C7—C8—H8	119.5 (10)
C2—C3—C4	120.72 (13)	C9—C8—H8	120.7 (9)
N1—C4—C3	117.06 (11)	C8—C9—H9	119.6 (9)
C3—C4—C5	119.51 (12)	C10—C9—H9	119.4 (9)
N1—C4—C5	123.43 (12)	C10—C11—H11	119.2 (9)
C4—C5—C6	119.98 (13)	C12—C11—H11	119.4 (9)
C1—C6—C5	120.41 (13)	C7—C12—H12	118.6 (9)
N2—C7—C8	123.21 (12)	C11—C12—H12	121.9 (9)
C8—C7—C12	119.88 (13)	C10—C13—H13	109.6 (10)
N2—C7—C12	116.87 (12)	C10—C13—H13'	110.4 (9)
C7—C8—C9	119.70 (13)	C14—C13—H13	108.5 (9)
C8—C9—C10	121.07 (13)	C14—C13—H13'	108.2 (10)
C9—C10—C13	120.62 (13)	H13—C13—H13'	108.3 (13)
C11—C10—C13	121.04 (13)	C13—C14—H14	111.0 (11)
C9—C10—C11	118.30 (13)	C13—C14—H14'	111.8 (10)
C10—C11—C12	121.32 (13)	C13—C14—H14"	112.1 (9)
C7—C12—C11	119.57 (13)	H14—C14—H14'	106.5 (14)
C10—C13—C14	111.73 (12)	H14—C14—H14"	108.1 (14)
C1—C2—H2	119.8 (9)	H14'—C14—H14"	107.1 (14)
C3—C2—H2	120.7 (9)

C4—N1—N2—C7	176.04 (11)	C4—C5—C6—C1	−0.3 (2)
N2—N1—C4—C3	172.74 (12)	N2—C7—C8—C9	179.83 (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—C12	148.57 (12)	C8—C7—C12—C11	4.4 (2)
O1—C1—C2—C3	177.87 (13)	C7—C8—C9—C10	−1.2 (2)
C6—C1—C2—C3	−2.4 (2)	C8—C9—C10—C11	2.9 (2)
O1—C1—C6—C5	−178.04 (12)	C8—C9—C10—C13	−174.80 (13)
C2—C1—C6—C5	2.2 (2)	C9—C10—C11—C12	−1.0 (2)
C1—C2—C3—C4	0.7 (2)	C13—C10—C11—C12	176.74 (13)
C2—C3—C4—N1	−179.53 (12)	C9—C10—C13—C14	80.03 (17)
C2—C3—C4—C5	1.2 (2)	C11—C10—C13—C14	−97.60 (17)
N1—C4—C5—C6	179.38 (12)	C10—C11—C12—C7	−2.7 (2)
C3—C4—C5—C6	−1.4 (2)

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+2, −y, −z+1; (v) −x+1, −y, −z+1; (vi) x, −y+1/2, z−1/2; (vii) −x+1, y+1/2, −z+1/2; (viii) x, −y+1/2, z+1/2; (ix) x, y+1, z; (x) −x+1, y−1/2, −z+1/2; (xi) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.91 (2)	1.98 (2)	2.8316 (15)	154.7 (17)
C3—H3···O1ⁱⁱⁱ	0.987 (15)	2.585 (15)	3.3541 (17)	134.7 (11)

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O
M_r	226.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.5261 (9), 13.4298 (15), 11.6412 (13)
β (°)	97.4001 (15)
V (Å³)	1166.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.33 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.956, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	8700, 2276, 1848
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.04
No. of reflections	2276
No. of parameters	210
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.24

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and PLUTO (Meetsma, 2007), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.91 (2)	1.98 (2)	2.8316 (15)	154.7 (17)
C3—H3···O1ⁱⁱ	0.987 (15)	2.585 (15)	3.3541 (17)	134.7 (11)

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2.

Acknowledgements

Albert Kiewiet is acknowledged for performing the MS analysis.

References

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