(E)-4-[(4-Diethyl­amino-2-hy­droxy­benzyl­idene)amino]­benzonitrile

Chang, M.-J.; Fang, T.-C.; Tsai, H.-Y.; Luo, M.-H.; Chen, K.-Y.

doi:10.1107/S1600536812008082

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o904-o905

doi:10.1107/S1600536812008082

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(E)-4-[(4-Diethylamino-2-hydroxybenzylidene)amino]benzonitrile

Ming-Jen Chang,^a Tzu-Chien Fang,^a Hsing-Yang Tsai,^a Ming-Hui Luo ^a and Kew-Yu Chen ^a ^*

^aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
^*Correspondence e-mail: kyuchen@fcu.edu.tw

(Received 20 February 2012; accepted 23 February 2012; online 29 February 2012)

The title compound, C₁₈H₁₉N₃O, displays an E conformation with respect to the C=N double bond. The dihedral angle between the mean planes of the two benzene rings is 24.49 (3)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by nonclassical intermolecular C—H⋯O hydrogen bonds to form an infinite one-dimensional chain along [010], generating a C(8) motif.

Related literature

For the preparation of the title compound, see: Shirinian et al. (2010 ). For the applications of proton transfer dyes, see: Chen & Pang (2010 ); Chuang et al. (2011 ); Han et al. (2010 ); Helal et al. (2010 ); Ikeda et al. (2010 ); Ito et al. (2011 ); Lim et al. (2011 ); Lins et al. (2010 ); Maupin et al. (2011 ); Santos et al. (2011 ); Tang et al. (2011 ). For related structures, see: Blagus & Kaitner (2011 ); Chen et al. (2011 ); Guo (2010 ); Manvizhi et al. (2011 ); Wang et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₉N₃O
M_r = 293.36
Monoclinic, P 2₁ /c
a = 15.361 (3) Å
b = 12.118 (2) Å
c = 8.7317 (14) Å
β = 100.717 (4)°
V = 1597.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.42 × 0.35 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2001 ) T_min = 0.436, T_max = 1.000
8867 measured reflections
3136 independent reflections
1405 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.171
S = 1.02
3136 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0A⋯N2	0.82	1.84	2.572 (3)	148
C4—H4A⋯Oⁱ	0.93	2.60	3.334 (3)	137
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812008082/rk2339sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008082/rk2339Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008082/rk2339Isup3.cml

checkCIF report

Comment top

The excited-state intramolecular proton transfer (ESIPT) reaction of N-(2-hydroxybenzylidene)aniline derivatives has been investigated, which incorporates transfer of a hydroxy proton to the imine nitrogen through an intramolecular six-membered-ring hydrogen-bonding system. The proton transfer dyes have found many important applications. Prototypical examples are probes for solvation dynamics (Chen & Pang, 2010; Lins et al., 2010) and biological environments (Lim et al., 2011; Maupin et al., 2011), photochromic materials (Ito et al., 2011), near-infrared fluorescent dyes (Ikeda et al., 2010), fluorescence microscopy imaging (Santos et al., 2011), chemosensors (Han et al., 2010; Helal et al., 2010) and recent application in the field of organic light emitting devices (Chuang et al., 2011; Tang et al., 2011).

The molecular structure of the title compound is shown in Fig. 1. The molecule displays a trans configuration about the central C═N imine double bond (Blagus & Kaitner, 2011; Guo, 2010; Manvizhi et al., 2011). The dihedral angle between the mean plane of two benzene rings is 24.49 (3)° (Wang et al., 2010) and an intramolecular O–H···N hydrogen bond (Table 1) generates an S(6) ring (Chen et al., 2011). In the crystal (Fig. 2), molecules are linked by non-classical intermolecular C–H···O hydrogen bonds (Table 1) to form an infinite one-dimensional chain along [0 1 0], generating a C(8) motif.

Related literature top

For the preparation of the title compound, see: Shirinian et al. (2010). For the applications of proton transfer dyes, see: Chen & Pang (2010); Chuang et al. (2011); Han et al. (2010); Helal et al. (2010); Ikeda et al. (2010); Ito et al. (2011); Lim et al. (2011); Lins et al. (2010); Maupin et al. (2011); Santos et al. (2011); Tang et al. (2011). For related structures, see: Blagus & Kaitner (2011); Chen et al. (2011); Guo (2010); Manvizhi et al. (2011); Wang et al. (2010).

Experimental top

The title compound was synthesized by the condensation reaction of 4-(diethylamino)-2-hydroxybenzaldehyde and 4-aminobenzonitrile according to the literature (Shirinian et al., 2010). Yellow parallelepiped crystals suitable for the crystallographic studies reported here were isolated over a period of five weeks by slow evaporation from a chloroform solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and the intramolecular O–H···N hydrogen bond (red dashed line). Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A section of the crystal packing of the title compound, viewed along the a axis. Green dashed lines denote the non-classical intermolecular C4–H4A···O hydrogen bonds.

(E)-4-[(4-Diethylamino-2-hydroxybenzylidene)amino]benzonitrile top

Crystal data top

C₁₈H₁₉N₃O	F(000) = 624
M_r = 293.36	D_x = 1.220 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1646 reflections
a = 15.361 (3) Å	θ = 2.2–22.6°
b = 12.118 (2) Å	µ = 0.08 mm⁻¹
c = 8.7317 (14) Å	T = 295 K
β = 100.717 (4)°	Parallelepiped, yellow
V = 1597.0 (5) Å³	0.42 × 0.35 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3136 independent reflections
Radiation source: fine-focus sealed tube	1405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 26.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker 2001)	h = −18→18
T_min = 0.436, T_max = 1.000	k = −14→14
8867 measured reflections	l = −7→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.075P)²] where P = (F_o² + 2F_c²)/3
3136 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₉N₃O	V = 1597.0 (5) Å³
M_r = 293.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.361 (3) Å	µ = 0.08 mm⁻¹
b = 12.118 (2) Å	T = 295 K
c = 8.7317 (14) Å	0.42 × 0.35 × 0.10 mm
β = 100.717 (4)°

Data collection top

Bruker SMART CCD diffractometer	3136 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2001)	1405 reflections with I > 2σ(I)
T_min = 0.436, T_max = 1.000	R_int = 0.054
8867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.02	Δρ_max = 0.13 e Å⁻³
3136 reflections	Δρ_min = −0.22 e Å⁻³
191 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O	−0.12526 (16)	−0.02917 (13)	0.1327 (2)	0.0914 (6)
H0A	−0.0756	−0.0162	0.1827	0.137 (16)*
N1	0.3699 (2)	0.1233 (3)	0.8181 (4)	0.1306 (11)
N2	0.01778 (14)	0.08093 (15)	0.2272 (3)	0.0735 (6)
N3	−0.34058 (17)	0.11544 (19)	−0.2774 (3)	0.0937 (6)
C1	0.3116 (2)	0.1190 (2)	0.7158 (4)	0.0969 (9)
C2	0.23844 (18)	0.1117 (2)	0.5869 (3)	0.0811 (7)
C3	0.20738 (19)	0.2036 (2)	0.4999 (4)	0.0871 (8)
H3A	0.2351	0.2714	0.5233	0.105*
C4	0.13636 (18)	0.1961 (2)	0.3796 (3)	0.0810 (8)
H4A	0.1161	0.2590	0.3230	0.097*
C5	0.09401 (18)	0.09504 (19)	0.3410 (3)	0.0702 (7)
C6	0.1265 (2)	0.0040 (2)	0.4290 (3)	0.0865 (8)
H6A	0.0992	−0.0641	0.4061	0.104*
C7	0.1975 (2)	0.0111 (2)	0.5485 (3)	0.0896 (8)
H7A	0.2185	−0.0518	0.6043	0.107*
C8	−0.00756 (15)	0.14955 (19)	0.1149 (3)	0.0701 (5)
H8A	0.0292	0.2083	0.1014	0.084*
C9	−0.08947 (16)	0.13804 (18)	0.0117 (3)	0.0701 (5)
C10	−0.11940 (19)	0.21569 (19)	−0.1058 (3)	0.0776 (8)
H10A	−0.0825	0.2744	−0.1187	0.093*
C11	−0.1997 (2)	0.2089 (2)	−0.2014 (3)	0.0807 (8)
H11A	−0.2159	0.2620	−0.2784	0.097*
C12	−0.25904 (18)	0.1226 (2)	−0.1858 (3)	0.0749 (7)
C13	−0.23028 (19)	0.04469 (19)	−0.0681 (3)	0.0778 (7)
H13A	−0.2681	−0.0127	−0.0535	0.093*
C14	−0.14852 (19)	0.05040 (18)	0.0257 (3)	0.0706 (7)
C15	−0.3678 (2)	0.1867 (3)	−0.4140 (3)	0.1043 (10)
H15A	−0.4051	0.1449	−0.4956	0.125*
H15B	−0.3156	0.2101	−0.4532	0.125*
C16	−0.4175 (2)	0.2868 (3)	−0.3755 (4)	0.1351 (13)
H16A	−0.4337	0.3316	−0.4670	0.203*
H16B	−0.3805	0.3287	−0.2954	0.203*
H16C	−0.4700	0.2639	−0.3394	0.203*
C17	−0.40588 (19)	0.0308 (2)	−0.2501 (3)	0.0937 (6)
H17A	−0.4654	0.0586	−0.2864	0.112*
H17B	−0.3990	0.0167	−0.1392	0.112*
C18	−0.3941 (3)	−0.0743 (3)	−0.3325 (5)	0.1237 (12)
H18A	−0.3371	−0.1052	−0.2905	0.164 (17)*
H18B	−0.3979	−0.0598	−0.4417	0.20 (2)*
H18C	−0.4396	−0.1255	−0.3185	0.187 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.1181 (17)	0.0591 (11)	0.0989 (14)	−0.0112 (10)	0.0253 (13)	0.0149 (10)
N1	0.110 (2)	0.132 (3)	0.143 (3)	0.0031 (19)	0.005 (2)	0.009 (2)
N2	0.0928 (16)	0.0518 (12)	0.0824 (15)	0.0057 (11)	0.0329 (13)	−0.0054 (11)
N3	0.1002 (14)	0.0906 (14)	0.0938 (13)	−0.0076 (10)	0.0270 (11)	0.0048 (11)
C1	0.089 (2)	0.091 (2)	0.115 (3)	0.0063 (19)	0.030 (2)	0.008 (2)
C2	0.0857 (19)	0.0719 (18)	0.093 (2)	0.0088 (16)	0.0367 (16)	0.0002 (16)
C3	0.097 (2)	0.0649 (17)	0.104 (2)	−0.0063 (15)	0.0315 (18)	−0.0012 (16)
C4	0.099 (2)	0.0546 (15)	0.094 (2)	0.0036 (14)	0.0300 (18)	0.0045 (14)
C5	0.0879 (18)	0.0504 (15)	0.0823 (18)	0.0087 (13)	0.0416 (15)	−0.0015 (13)
C6	0.113 (2)	0.0522 (16)	0.099 (2)	0.0024 (15)	0.0320 (19)	−0.0009 (15)
C7	0.114 (2)	0.0623 (18)	0.097 (2)	0.0123 (16)	0.031 (2)	0.0082 (15)
C8	0.0912 (13)	0.0506 (9)	0.0793 (14)	−0.0041 (10)	0.0439 (10)	−0.0043 (10)
C9	0.0912 (13)	0.0506 (9)	0.0793 (14)	−0.0041 (10)	0.0439 (10)	−0.0043 (10)
C10	0.107 (2)	0.0544 (15)	0.0822 (18)	−0.0098 (14)	0.0462 (17)	0.0021 (14)
C11	0.109 (2)	0.0652 (16)	0.0757 (18)	−0.0014 (16)	0.0364 (17)	0.0059 (13)
C12	0.0949 (19)	0.0610 (15)	0.0773 (18)	−0.0038 (15)	0.0380 (16)	−0.0025 (13)
C13	0.099 (2)	0.0571 (15)	0.0863 (19)	−0.0138 (14)	0.0393 (16)	−0.0013 (14)
C14	0.100 (2)	0.0471 (13)	0.0736 (17)	0.0011 (14)	0.0384 (16)	0.0006 (12)
C15	0.119 (2)	0.116 (3)	0.079 (2)	−0.010 (2)	0.0204 (18)	0.0069 (18)
C16	0.160 (3)	0.121 (3)	0.126 (3)	0.040 (3)	0.032 (2)	0.031 (2)
C17	0.1002 (14)	0.0906 (14)	0.0938 (13)	−0.0076 (10)	0.0270 (11)	0.0048 (11)
C18	0.134 (4)	0.110 (3)	0.135 (4)	−0.024 (3)	0.048 (3)	−0.024 (2)

Geometric parameters (Å, º) top

O—C14	1.344 (3)	C9—C10	1.405 (3)
O—H0A	0.8200	C9—C14	1.417 (3)
N1—C1	1.143 (4)	C10—C11	1.357 (3)
N2—C8	1.290 (3)	C10—H10A	0.9300
N2—C5	1.398 (3)	C11—C12	1.410 (3)
N3—C12	1.358 (3)	C11—H11A	0.9300
N3—C17	1.484 (3)	C12—C13	1.405 (3)
N3—C15	1.469 (3)	C13—C14	1.368 (3)
C1—C2	1.437 (4)	C13—H13A	0.9300
C2—C3	1.383 (3)	C15—C16	1.504 (4)
C2—C7	1.383 (3)	C15—H15A	0.9700
C3—C4	1.369 (3)	C15—H15B	0.9700
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.398 (3)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.384 (3)	C17—C18	1.490 (4)
C6—C7	1.365 (3)	C17—H17A	0.9700
C6—H6A	0.9300	C17—H17B	0.9700
C7—H7A	0.9300	C18—H18A	0.9600
C8—C9	1.412 (3)	C18—H18B	0.9600
C8—H8A	0.9300	C18—H18C	0.9600

C14—O—H0A	109.5	C12—C11—H11A	119.5
C8—N2—C5	123.8 (2)	N3—C12—C13	121.2 (2)
C12—N3—C17	121.8 (2)	N3—C12—C11	122.2 (3)
C12—N3—C15	122.2 (2)	C13—C12—C11	116.6 (3)
C17—N3—C15	116.0 (2)	C14—C13—C12	122.2 (2)
N1—C1—C2	179.0 (4)	C14—C13—H13A	118.9
C3—C2—C7	118.8 (3)	C12—C13—H13A	118.9
C3—C2—C1	121.3 (3)	O—C14—C13	118.4 (2)
C7—C2—C1	119.9 (3)	O—C14—C9	120.4 (3)
C2—C3—C4	120.8 (3)	C13—C14—C9	121.2 (2)
C2—C3—H3A	119.6	N3—C15—C16	111.8 (2)
C4—C3—H3A	119.6	N3—C15—H15A	109.2
C3—C4—C5	120.8 (3)	C16—C15—H15A	109.2
C3—C4—H4A	119.6	N3—C15—H15B	109.2
C5—C4—H4A	119.6	C16—C15—H15B	109.2
N2—C5—C6	117.7 (2)	H15A—C15—H15B	107.9
N2—C5—C4	124.7 (2)	C15—C16—H16A	109.5
C6—C5—C4	117.5 (3)	C15—C16—H16B	109.5
C5—C6—C7	121.9 (3)	H16A—C16—H16B	109.5
C5—C6—H6A	119.1	C15—C16—H16C	109.5
C7—C6—H6A	119.1	H16A—C16—H16C	109.5
C2—C7—C6	120.3 (3)	H16B—C16—H16C	109.5
C2—C7—H7A	119.9	N3—C17—C18	111.5 (2)
C6—C7—H7A	119.9	N3—C17—H17A	109.3
N2—C8—C9	121.9 (2)	C18—C17—H17A	109.3
N2—C8—H8A	119.0	N3—C17—H17B	109.3
C9—C8—H8A	119.0	C18—C17—H17B	109.3
C10—C9—C14	115.9 (3)	H17A—C17—H17B	108.0
C10—C9—C8	122.1 (2)	C17—C18—H18A	109.5
C14—C9—C8	121.9 (2)	C17—C18—H18B	109.5
C11—C10—C9	123.0 (2)	H18A—C18—H18B	109.5
C11—C10—H10A	118.5	C17—C18—H18C	109.5
C9—C10—H10A	118.5	H18A—C18—H18C	109.5
C10—C11—C12	121.0 (2)	H18B—C18—H18C	109.5
C10—C11—H11A	119.5

C7—C2—C3—C4	1.2 (4)	C17—N3—C12—C13	4.9 (4)
C1—C2—C3—C4	−178.5 (2)	C15—N3—C12—C13	−171.7 (2)
C2—C3—C4—C5	−0.6 (4)	C17—N3—C12—C11	−173.9 (2)
C8—N2—C5—C6	−163.3 (2)	C15—N3—C12—C11	9.5 (4)
C8—N2—C5—C4	21.3 (3)	C10—C11—C12—N3	178.3 (2)
C3—C4—C5—N2	175.6 (2)	C10—C11—C12—C13	−0.5 (3)
C3—C4—C5—C6	0.2 (4)	N3—C12—C13—C14	−179.8 (2)
N2—C5—C6—C7	−176.2 (2)	C11—C12—C13—C14	−1.0 (3)
C4—C5—C6—C7	−0.5 (4)	C12—C13—C14—O	−178.2 (2)
C3—C2—C7—C6	−1.5 (4)	C12—C13—C14—C9	2.1 (4)
C1—C2—C7—C6	178.2 (2)	C10—C9—C14—O	178.8 (2)
C5—C6—C7—C2	1.1 (4)	C8—C9—C14—O	−4.4 (3)
C5—N2—C8—C9	−173.49 (19)	C10—C9—C14—C13	−1.5 (3)
N2—C8—C9—C10	176.6 (2)	C8—C9—C14—C13	175.3 (2)
N2—C8—C9—C14	0.0 (3)	C12—N3—C15—C16	−95.1 (3)
C14—C9—C10—C11	0.0 (3)	C17—N3—C15—C16	88.1 (3)
C8—C9—C10—C11	−176.8 (2)	C12—N3—C17—C18	−87.4 (3)
C9—C10—C11—C12	1.0 (4)	C15—N3—C17—C18	89.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N2	0.82	1.84	2.572 (3)	148
C4—H4A···Oⁱ	0.93	2.60	3.334 (3)	137

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₃O
M_r	293.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	15.361 (3), 12.118 (2), 8.7317 (14)
β (°)	100.717 (4)
V (Å³)	1597.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.42 × 0.35 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2001)
T_min, T_max	0.436, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8867, 3136, 1405
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.171, 1.02
No. of reflections	3136
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N2	0.82	1.84	2.572 (3)	148
C4—H4A···Oⁱ	0.93	2.60	3.334 (3)	137

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the National Science Council (grant No. NSC 99-2113-M-035-001-MY2) and Feng Chia University in Taiwan.

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