3-{[(4Z)-1,2-Dimethyl-5-oxoimidazol-4-yl-idene]meth-yl}-4-hy-droxy-benzonitrile.

In the title compound, C(13)H(11)N(3)O(2), an intra-molecular 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 mol-ecules are linked by dual C-H⋯O(carbon-yl) hydrogen bonds to form a dimer with an R(2) (2)(14) graph-set motif. A C-H⋯O(hy-droxy) inter-action links pairs of mol-ecules into another type of cyclic dimer with an R(2) (2)(18) motif. The mol-ecules are further linked by C-H⋯N inter-actions to form layers parallel to (001). Offset π-π stacking [3.3877 (8) Å] is observed in the crystal structure, with an inter-planar 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 = 241.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 0.94

2048 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007532/zl2452sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812007532/zl2452Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H11N3O2	F(000) = 1008
Mr = 241.25	Dx = 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

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

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(Fo2) + (0.0695P)2] where P = (Fo2 + 2Fc2)/3
2048 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···N3iv	0.96	2.64	3.586 (3)	169

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⋯N3iv	0.96	2.64	3.586 (3)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .