3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-yl­idene]meth­yl}-4-hy­droxy­benzonitrile

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

doi:10.1107/S1600536812007532

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o867-o868

doi:10.1107/S1600536812007532

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3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile

Hsing-Yang Tsai,^a Ming-Jen Chang,^a Tzu-Chien Fang,^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 9 February 2012; accepted 20 February 2012; online 29 February 2012)

In the title compound, C₁₃H₁₁N₃O₂, an intramolecular O—H⋯N hydrogen bond generates an S(7) ring. The dihedral angle between the mean plane of the benzene ring and the imidazolidinone ring is 3.05 (2)°. In the crystal, inversion-related molecules are linked by dual C—H⋯O_carbonyl hydrogen bonds to form a dimer with an R₂²(14) graph-set motif. A C—H⋯O_hydroxy interaction links pairs of molecules into another type of cyclic dimer with an R₂²(18) motif. The molecules are further linked by C—H⋯N interactions to form layers parallel to (001). Offset π–π stacking [3.3877 (8) Å] is observed in the crystal structure, with an interplanar spacing between the planes of neighboring benzene rings of 3.444 (1) Å.

Related literature

For the spectroscopy and preparation of the title compound, see: Chuang et al. (2011 ). For the applications of proton-transfer dyes, see: Chen & Pang (2010 ); Gryko et al. (2010 ); 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 a related structure, see: Chen et al. (2007 ). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₁N₃O₂
M_r = 241.25
Monoclinic, C 2/c
a = 24.9655 (10) Å
b = 3.8349 (1) Å
c = 26.7584 (10) Å
β = 115.488 (5)°
V = 2312.52 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.24 × 0.2 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.811, T_max = 0.999
15085 measured reflections
2048 independent reflections
1364 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.112
S = 0.94
2048 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.85	2.591 (2)	150
C12—H12⋯O1ⁱ	0.93	2.47	3.262 (2)	143
C5—H5C⋯O2ⁱⁱ	0.96	2.67	3.566 (3)	156
C4—H4A⋯N3ⁱⁱⁱ	0.96	2.63	3.436 (3)	142
C5—H5A⋯N3^iv	0.96	2.64	3.586 (3)	169
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ ; (iv) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007532/zl2452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007532/zl2452Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007532/zl2452Isup3.cml

checkCIF report

Comment top

The excited-state intramolecular proton transfer (ESIPT) reaction of the title compound has been investigated recently (Chuang et al., 2011), which incorporates transfer of a hydroxy proton to the imine nitrogen through an intramolecular seven-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), fluorescence microscopy imaging (Santos et al., 2011), near-infrared fluorescent dyes (Ikeda et al., 2010), photochromic materials (Ito et al., 2011), chemosensors (Han et al., 2010; Helal et al., 2010) and recent application in the field of organic light emitting devices (Gryko et al., 2010; Tang et al., 2011).

The molecular structure of the title compound is shown in Fig. 1. As expected, the molecule possesses an intramolecular O—H···N hydrogen bond, which generates an S(7) ring (Chen et al., 2007). The dihedral angle between the mean plane of the benzene ring and the imidazolidinone ring is 3.05 (2)°. In the crystal (Fig. 2), inversion-related molecules are linked by pairs of C12—H12···O1 hydrogen bonds, forming a cyclic dimer with an R₂²(14) graph-set motif, Fig. 2 (Bernstein et al., 1995). In addition, the C5—H5C···O2 interaction links a pair of molecules into another type of cyclic dimer with an R₂²(18) graph-set motif. Molecules are further stabilized by intermolecular C—H···N interactions involving the methyl groups of C4 and C5 to form layers parallel to (001). See Table 1 for numerical details of the hdrogen bonds and symmetry operators. Offset π–π stacking is observed in the crystal structure with an interplanar spacing between planes of neighboring benzene rings of 3.444 (1) Å. The closest centroid–centroid distance [symmetry code: x, -1 + y, z] is 4.8350 (12) Å (Cg1 and Cg2 are the centroids of the N1/N2/C1–C3 and C7–C12 rings, respectively).

Related literature top

For the spectroscopy and preparation of the title compound, see: Chuang et al. (2011). For the applications of proton-transfer dyes, see: Chen & Pang (2010); Gryko et al. (2010); 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 a related structure, see: Chen et al. (2007). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized according to the literature (Chuang et al., 2011). Yellow needle-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of six 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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. A section of the crystal packing of the title compound, viewed down the c axis. Green dashed lines denote the intermolecular C12—H12···O1 hydrogen bonds [symmetry code: -x + 1, -y + 1, -z + 1].

3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}- 4-hydroxybenzonitrile top

Crystal data top

C₁₃H₁₁N₃O₂	F(000) = 1008
M_r = 241.25	D_x = 1.386 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3648 reflections
a = 24.9655 (10) Å	θ = 3.1–26.9°
b = 3.8349 (1) Å	µ = 0.10 mm⁻¹
c = 26.7584 (10) Å	T = 150 K
β = 115.488 (5)°	Prism, colourless
V = 2312.52 (17) Å³	0.24 × 0.2 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	2048 independent reflections
Radiation source: fine-focus sealed tube	1364 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −28→28
T_min = 0.811, T_max = 0.999	k = −4→4
15085 measured reflections	l = −31→31

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0695P)²] where P = (F_o² + 2F_c²)/3
2048 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O₂	V = 2312.52 (17) Å³
M_r = 241.25	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.9655 (10) Å	µ = 0.10 mm⁻¹
b = 3.8349 (1) Å	T = 150 K
c = 26.7584 (10) Å	0.24 × 0.2 × 0.15 mm
β = 115.488 (5)°

Data collection top

Bruker SMART CCD diffractometer	2048 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1364 reflections with I > 2σ(I)
T_min = 0.811, T_max = 0.999	R_int = 0.067
15085 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.94	Δρ_max = 0.25 e Å⁻³
2048 reflections	Δρ_min = −0.29 e Å⁻³
166 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.41612 (5)	0.5235 (4)	0.49910 (5)	0.0339 (4)
O2	0.56473 (6)	0.0638 (3)	0.71292 (5)	0.0339 (4)
H2	0.5299	0.0855	0.6907	0.051*
N1	0.38975 (6)	0.5881 (4)	0.57176 (6)	0.0246 (4)
N2	0.46849 (6)	0.3562 (4)	0.64190 (6)	0.0251 (4)
N3	0.74916 (8)	−0.3544 (5)	0.59904 (8)	0.0484 (6)
C1	0.41673 (8)	0.5046 (5)	0.62728 (8)	0.0245 (5)
C2	0.42684 (8)	0.4890 (5)	0.54770 (8)	0.0235 (5)
C3	0.47832 (7)	0.3369 (5)	0.59435 (7)	0.0221 (4)
C4	0.33058 (8)	0.7365 (5)	0.54035 (8)	0.0331 (5)
H4A	0.3244	0.9241	0.5610	0.050*
H4B	0.3012	0.5594	0.5339	0.050*
H4C	0.3274	0.8233	0.5055	0.050*
C5	0.38931 (9)	0.5833 (5)	0.66510 (8)	0.0347 (5)
H5A	0.3499	0.4879	0.6503	0.052*
H5B	0.3874	0.8314	0.6689	0.052*
H5C	0.4127	0.4818	0.7007	0.052*
C6	0.52658 (8)	0.2123 (5)	0.58951 (7)	0.0231 (5)
H6	0.5242	0.2299	0.5539	0.028*
C7	0.58150 (7)	0.0561 (4)	0.62927 (7)	0.0212 (5)
C8	0.59742 (8)	−0.0138 (5)	0.68578 (8)	0.0247 (5)
C9	0.65172 (8)	−0.1766 (5)	0.71763 (8)	0.0291 (5)
H9	0.6619	−0.2264	0.7546	0.035*
C10	0.69024 (8)	−0.2644 (5)	0.69540 (8)	0.0277 (5)
H10	0.7262	−0.3715	0.7173	0.033*
C11	0.67552 (8)	−0.1933 (5)	0.64034 (8)	0.0251 (5)
C12	0.62173 (8)	−0.0365 (5)	0.60796 (8)	0.0241 (5)
H12	0.6121	0.0087	0.5709	0.029*
C13	0.71618 (8)	−0.2836 (5)	0.61677 (8)	0.0323 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0263 (8)	0.0464 (9)	0.0299 (9)	0.0084 (6)	0.0128 (6)	0.0040 (7)
O2	0.0225 (7)	0.0537 (10)	0.0266 (8)	0.0042 (6)	0.0116 (6)	0.0030 (7)
N1	0.0157 (8)	0.0296 (10)	0.0305 (9)	0.0027 (7)	0.0119 (7)	−0.0007 (8)
N2	0.0192 (9)	0.0305 (10)	0.0287 (9)	−0.0006 (7)	0.0132 (7)	−0.0024 (8)
N3	0.0312 (11)	0.0575 (14)	0.0624 (14)	0.0070 (9)	0.0257 (10)	−0.0083 (11)
C1	0.0210 (11)	0.0246 (11)	0.0303 (11)	−0.0034 (9)	0.0133 (9)	−0.0035 (9)
C2	0.0198 (10)	0.0266 (11)	0.0261 (12)	−0.0005 (8)	0.0118 (9)	−0.0009 (9)
C3	0.0189 (10)	0.0239 (11)	0.0259 (10)	−0.0016 (8)	0.0118 (8)	−0.0012 (8)
C4	0.0192 (10)	0.0351 (12)	0.0439 (13)	0.0077 (9)	0.0124 (10)	0.0028 (10)
C5	0.0338 (12)	0.0395 (13)	0.0385 (13)	0.0029 (10)	0.0230 (11)	−0.0006 (10)
C6	0.0205 (10)	0.0249 (11)	0.0249 (10)	−0.0020 (8)	0.0108 (8)	−0.0015 (9)
C7	0.0172 (10)	0.0187 (10)	0.0279 (11)	−0.0028 (8)	0.0099 (9)	−0.0025 (8)
C8	0.0185 (10)	0.0256 (11)	0.0314 (12)	−0.0036 (8)	0.0119 (9)	−0.0027 (9)
C9	0.0248 (11)	0.0308 (12)	0.0273 (11)	−0.0016 (9)	0.0070 (9)	0.0026 (9)
C10	0.0181 (10)	0.0244 (11)	0.0363 (12)	0.0012 (8)	0.0075 (9)	0.0005 (9)
C11	0.0180 (10)	0.0211 (10)	0.0368 (12)	0.0005 (8)	0.0124 (9)	−0.0039 (9)
C12	0.0206 (10)	0.0245 (11)	0.0281 (11)	0.0003 (8)	0.0115 (9)	−0.0008 (9)
C13	0.0209 (11)	0.0307 (12)	0.0425 (13)	0.0032 (9)	0.0109 (10)	−0.0009 (10)

Geometric parameters (Å, º) top

O1—C2	1.217 (2)	C5—H5A	0.9600
O2—C8	1.339 (2)	C5—H5B	0.9600
O2—H2	0.8200	C5—H5C	0.9600
N1—C1	1.379 (2)	C6—C7	1.454 (2)
N1—C2	1.389 (2)	C6—H6	0.9300
N1—C4	1.464 (2)	C7—C12	1.397 (2)
N2—C1	1.308 (2)	C7—C8	1.414 (2)
N2—C3	1.398 (2)	C8—C9	1.400 (3)
N3—C13	1.146 (2)	C9—C10	1.373 (2)
C1—C5	1.476 (2)	C9—H9	0.9300
C2—C3	1.473 (2)	C10—C11	1.383 (3)
C3—C6	1.353 (2)	C10—H10	0.9300
C4—H4A	0.9600	C11—C12	1.384 (3)
C4—H4B	0.9600	C11—C13	1.449 (3)
C4—H4C	0.9600	C12—H12	0.9300

C8—O2—H2	109.5	H5A—C5—H5C	109.5
C1—N1—C2	108.77 (15)	H5B—C5—H5C	109.5
C1—N1—C4	127.81 (15)	C3—C6—C7	132.33 (17)
C2—N1—C4	123.33 (15)	C3—C6—H6	113.8
C1—N2—C3	106.78 (15)	C7—C6—H6	113.8
N2—C1—N1	112.63 (16)	C12—C7—C8	117.87 (17)
N2—C1—C5	125.00 (17)	C12—C7—C6	115.02 (16)
N1—C1—C5	122.36 (16)	C8—C7—C6	127.10 (16)
O1—C2—N1	125.56 (17)	O2—C8—C9	115.19 (17)
O1—C2—C3	131.25 (17)	O2—C8—C7	125.55 (17)
N1—C2—C3	103.19 (15)	C9—C8—C7	119.26 (17)
C6—C3—N2	128.19 (17)	C10—C9—C8	121.40 (18)
C6—C3—C2	123.15 (17)	C10—C9—H9	119.3
N2—C3—C2	108.63 (14)	C8—C9—H9	119.3
N1—C4—H4A	109.5	C9—C10—C11	119.90 (17)
N1—C4—H4B	109.5	C9—C10—H10	120.1
H4A—C4—H4B	109.5	C11—C10—H10	120.1
N1—C4—H4C	109.5	C10—C11—C12	119.61 (17)
H4A—C4—H4C	109.5	C10—C11—C13	120.11 (17)
H4B—C4—H4C	109.5	C12—C11—C13	120.28 (18)
C1—C5—H5A	109.5	C11—C12—C7	121.95 (18)
C1—C5—H5B	109.5	C11—C12—H12	119.0
H5A—C5—H5B	109.5	C7—C12—H12	119.0
C1—C5—H5C	109.5	N3—C13—C11	178.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.85	2.591 (2)	150
C12—H12···O1ⁱ	0.93	2.47	3.262 (2)	143
C5—H5C···O2ⁱⁱ	0.96	2.67	3.566 (3)	156
C4—H4A···N3ⁱⁱⁱ	0.96	2.63	3.436 (3)	142
C5—H5A···N3^iv	0.96	2.64	3.586 (3)	169

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y, −z+3/2; (iii) x−1/2, y+3/2, z; (iv) x−1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O₂
M_r	241.25
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	24.9655 (10), 3.8349 (1), 26.7584 (10)
β (°)	115.488 (5)
V (Å³)	2312.52 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.24 × 0.2 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.811, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	15085, 2048, 1364
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 0.94
No. of reflections	2048
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.85	2.591 (2)	150
C12—H12···O1ⁱ	0.93	2.47	3.262 (2)	143
C5—H5C···O2ⁱⁱ	0.96	2.67	3.566 (3)	156
C4—H4A···N3ⁱⁱⁱ	0.96	2.63	3.436 (3)	142
C5—H5A···N3^iv	0.96	2.64	3.586 (3)	169

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y, −z+3/2; (iii) x−1/2, y+3/2, z; (iv) x−1/2, y+1/2, z.

Acknowledgements

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

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o867-o868

doi:10.1107/S1600536812007532

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-{[(4Z)-1,2-Di­methyl-5-oxoimidazol-4-yl­­idene]meth­yl}-4-hy­dr­oxy­benzo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-ylidene]methyl}-4-hydroxybenzonitrile