(Z)-1-(2-Hy-droxy-eth-yl)-4-(2-meth-oxy-benzyl-idene)-2-methyl-1H-imidazol-5(4H)-one.

In the title compound, C14H16N2O3, an analog of the chromophore in green fluorescent protein, the meth-oxy-phenyl substituent and the imidazole N adopt a Z conformation with respect to the C=C bond. Aside from the hy-droxy-ethyl group, the mol-ecule is approximately planar, with the five- and six-membered ring planes forming a dihedral angle of 9.3 (1)°. An intra-molecular C-H⋯N contact occurs. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules, forming chains along the b-axis direction. C-H⋯O hydrogen bonds are also observed.

Related literature

For background to green fluorescent protein, see: Shimomura et al. (1962 ▶); Shimomura (2009 ▶); Remington (2006 ▶); Tsien (1998 ▶); Chalfie et al. (1994 ▶); Prasher et al. (1992 ▶). For the synthesis, see: Yampolsky et al. (2005 ▶); Bailly et al.(2004 ▶); Wenge & Wagenknecht (2011 ▶). For related structures, see: Naumov et al. (2010 ▶); Bhattacharjya et al. (2005 ▶); Oshimi et al. (2002 ▶); Dong et al. (2009 ▶). For Bijvoet pair analysis, see: Hooft et al. (2008 ▶).

Experimental

Crystal data

C14H16N2O3

M = 260.29

Monoclinic,

a = 9.2188 (5) Å

b = 7.2767 (4) Å

c = 9.5620 (5) Å

β = 93.625 (6)°

V = 640.16 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 90 K

0.35 × 0.25 × 0.17 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.967, T max = 0.984

9385 measured reflections

4943 independent reflections

4720 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 1.06

4943 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1605 Friedel pairs

Flack parameter: −0.9 (5)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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, 2012 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007770/sj5304sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007770/sj5304Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007770/sj5304Isup3.cml

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

C14H16N2O3	F(000) = 276
Mr = 260.29	Dx = 1.350 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6251 reflections
a = 9.2188 (5) Å	θ = 3.2–37.7°
b = 7.2767 (4) Å	µ = 0.10 mm−1
c = 9.5620 (5) Å	T = 90 K
β = 93.625 (6)°	Needle, yellow
V = 640.16 (6) Å3	0.35 × 0.25 × 0.17 mm
Z = 2

Bruker Kappa APEXII DUO CCD diffractometer	4943 independent reflections
Radiation source: fine-focus sealed tube	4720 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 37.8°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→13
Tmin = 0.967, Tmax = 0.984	k = −8→12
9385 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.0209P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4943 reflections	Δρmax = 0.42 e Å−3
177 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 1605 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.9 (5)

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	0.46857 (7)	0.27870 (9)	0.59877 (7)	0.01987 (12)
O2	0.52843 (7)	0.87448 (9)	0.79824 (7)	0.01835 (11)
O3	0.11188 (6)	0.14749 (9)	0.32174 (6)	0.01679 (11)
H3O	0.0433 (16)	0.064 (2)	0.3128 (15)	0.025*
N1	0.23432 (7)	0.16329 (9)	0.60614 (7)	0.01255 (10)
N2	0.12395 (7)	0.39039 (9)	0.72030 (7)	0.01344 (11)
C1	0.34363 (8)	0.29285 (10)	0.63215 (8)	0.01374 (12)
C2	0.10888 (8)	0.22969 (11)	0.65921 (7)	0.01237 (11)
C3	0.26991 (8)	0.44057 (10)	0.70824 (8)	0.01307 (12)
C4	0.25234 (8)	0.00285 (10)	0.51780 (8)	0.01355 (12)
H4A	0.1748	−0.0877	0.5335	0.016*
H4B	0.3473	−0.0558	0.5431	0.016*
C5	0.24500 (8)	0.05885 (12)	0.36415 (8)	0.01478 (12)
H5A	0.3268	0.1428	0.3481	0.018*
H5B	0.2563	−0.0519	0.3057	0.018*
C6	−0.02821 (9)	0.12268 (11)	0.64852 (9)	0.01714 (13)
H6A	−0.1019	0.1860	0.7002	0.026*
H6B	−0.0108	0.0001	0.6885	0.026*
H6C	−0.0626	0.1112	0.5498	0.026*
C7	0.34421 (8)	0.59176 (10)	0.75311 (8)	0.01367 (12)
H7	0.4419	0.5965	0.7272	0.016*
C8	0.29964 (8)	0.74799 (10)	0.83426 (7)	0.01242 (11)
C9	0.16563 (8)	0.75856 (11)	0.89605 (8)	0.01475 (12)
H9	0.0969	0.6622	0.8807	0.018*
C10	0.13176 (9)	0.90681 (13)	0.97897 (8)	0.01816 (14)
H10	0.0408	0.9115	1.0203	0.022*
C11	0.23173 (9)	1.04896 (12)	1.00136 (8)	0.01849 (14)
H11	0.2081	1.1511	1.0575	0.022*
C12	0.36595 (9)	1.04289 (11)	0.94234 (8)	0.01678 (13)
H12	0.4338	1.1400	0.9584	0.020*
C13	0.39992 (8)	0.89311 (10)	0.85941 (7)	0.01325 (11)
C14	0.64199 (10)	1.00233 (13)	0.83403 (11)	0.02252 (16)
H14A	0.6138	1.1243	0.7984	0.034*
H14B	0.7312	0.9629	0.7921	0.034*
H14C	0.6590	1.0076	0.9362	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0123 (2)	0.0188 (3)	0.0289 (3)	−0.0010 (2)	0.0046 (2)	−0.0056 (2)
O2	0.0164 (2)	0.0172 (3)	0.0220 (2)	−0.0070 (2)	0.00527 (19)	−0.0056 (2)
O3	0.0147 (2)	0.0152 (2)	0.0201 (2)	0.00069 (19)	−0.00168 (18)	0.0018 (2)
N1	0.0115 (2)	0.0103 (2)	0.0159 (2)	−0.00049 (19)	0.00164 (18)	−0.0022 (2)
N2	0.0120 (2)	0.0111 (2)	0.0174 (2)	−0.00118 (19)	0.00251 (19)	−0.0013 (2)
C1	0.0126 (3)	0.0119 (3)	0.0168 (3)	−0.0009 (2)	0.0014 (2)	−0.0022 (2)
C2	0.0119 (3)	0.0103 (2)	0.0150 (3)	−0.0010 (2)	0.0021 (2)	0.0005 (2)
C3	0.0120 (3)	0.0109 (3)	0.0164 (3)	−0.0007 (2)	0.0021 (2)	−0.0018 (2)
C4	0.0156 (3)	0.0096 (3)	0.0155 (3)	0.0011 (2)	0.0008 (2)	−0.0015 (2)
C5	0.0141 (3)	0.0154 (3)	0.0149 (3)	0.0009 (2)	0.0013 (2)	−0.0004 (2)
C6	0.0132 (3)	0.0135 (3)	0.0250 (3)	−0.0035 (2)	0.0034 (2)	−0.0009 (3)
C7	0.0129 (3)	0.0116 (3)	0.0167 (3)	−0.0018 (2)	0.0020 (2)	−0.0026 (2)
C8	0.0134 (3)	0.0109 (3)	0.0129 (2)	−0.0003 (2)	0.0002 (2)	−0.0008 (2)
C9	0.0132 (3)	0.0157 (3)	0.0154 (3)	0.0001 (2)	0.0012 (2)	−0.0022 (2)
C10	0.0176 (3)	0.0191 (3)	0.0179 (3)	0.0020 (3)	0.0029 (2)	−0.0041 (3)
C11	0.0224 (3)	0.0162 (3)	0.0169 (3)	0.0018 (3)	0.0012 (2)	−0.0048 (3)
C12	0.0207 (3)	0.0132 (3)	0.0162 (3)	−0.0015 (3)	0.0000 (2)	−0.0028 (2)
C13	0.0149 (3)	0.0117 (3)	0.0132 (2)	−0.0019 (2)	0.0009 (2)	−0.0006 (2)
C14	0.0187 (3)	0.0176 (3)	0.0313 (4)	−0.0080 (3)	0.0022 (3)	−0.0031 (3)

O1—C1	1.2188 (9)	C6—H6A	0.9800
O2—C13	1.3608 (9)	C6—H6B	0.9800
O2—C14	1.4259 (10)	C6—H6C	0.9800
O3—C5	1.4225 (10)	C7—C8	1.4504 (10)
O3—H3O	0.879 (16)	C7—H7	0.9500
N1—C2	1.3794 (9)	C8—C9	1.4048 (10)
N1—C1	1.3908 (10)	C8—C13	1.4141 (10)
N1—C4	1.4566 (10)	C9—C10	1.3861 (11)
N2—C2	1.3105 (10)	C9—H9	0.9500
N2—C3	1.4061 (10)	C10—C11	1.3929 (12)
C1—C3	1.4863 (10)	C10—H10	0.9500
C2—C6	1.4825 (11)	C11—C12	1.3928 (12)
C3—C7	1.3515 (11)	C11—H11	0.9500
C4—C5	1.5221 (11)	C12—C13	1.3950 (11)
C4—H4A	0.9900	C12—H12	0.9500
C4—H4B	0.9900	C14—H14A	0.9800
C5—H5A	0.9900	C14—H14B	0.9800
C5—H5B	0.9900	C14—H14C	0.9800
C13—O2—C14	118.54 (7)	C2—C6—H6C	109.5
C5—O3—H3O	108.3 (10)	H6A—C6—H6C	109.5
C2—N1—C1	108.16 (6)	H6B—C6—H6C	109.5
C2—N1—C4	128.54 (6)	C3—C7—C8	130.76 (7)
C1—N1—C4	122.62 (6)	C3—C7—H7	114.6
C2—N2—C3	105.67 (6)	C8—C7—H7	114.6
O1—C1—N1	125.59 (7)	C9—C8—C13	118.06 (7)
O1—C1—C3	131.16 (7)	C9—C8—C7	123.67 (7)
N1—C1—C3	103.25 (6)	C13—C8—C7	118.17 (6)
N2—C2—N1	114.13 (6)	C10—C9—C8	121.27 (7)
N2—C2—C6	124.42 (7)	C10—C9—H9	119.4
N1—C2—C6	121.44 (7)	C8—C9—H9	119.4
C7—C3—N2	130.83 (7)	C9—C10—C11	119.67 (7)
C7—C3—C1	120.39 (7)	C9—C10—H10	120.2
N2—C3—C1	108.78 (6)	C11—C10—H10	120.2
N1—C4—C5	110.21 (6)	C12—C11—C10	120.68 (7)
N1—C4—H4A	109.6	C12—C11—H11	119.7
C5—C4—H4A	109.6	C10—C11—H11	119.7
N1—C4—H4B	109.6	C11—C12—C13	119.49 (7)
C5—C4—H4B	109.6	C11—C12—H12	120.3
H4A—C4—H4B	108.1	C13—C12—H12	120.3
O3—C5—C4	112.42 (6)	O2—C13—C12	123.71 (7)
O3—C5—H5A	109.1	O2—C13—C8	115.47 (6)
C4—C5—H5A	109.1	C12—C13—C8	120.81 (7)
O3—C5—H5B	109.1	O2—C14—H14A	109.5
C4—C5—H5B	109.1	O2—C14—H14B	109.5
H5A—C5—H5B	107.9	H14A—C14—H14B	109.5
C2—C6—H6A	109.5	O2—C14—H14C	109.5
C2—C6—H6B	109.5	H14A—C14—H14C	109.5
H6A—C6—H6B	109.5	H14B—C14—H14C	109.5
C2—N1—C1—O1	−179.73 (8)	N1—C4—C5—O3	−58.15 (8)
C4—N1—C1—O1	−8.46 (12)	N2—C3—C7—C8	3.33 (14)
C2—N1—C1—C3	0.98 (8)	C1—C3—C7—C8	−176.57 (7)
C4—N1—C1—C3	172.26 (6)	C3—C7—C8—C9	7.28 (13)
C3—N2—C2—N1	0.45 (8)	C3—C7—C8—C13	−176.50 (8)
C3—N2—C2—C6	179.24 (7)	C13—C8—C9—C10	0.22 (11)
C1—N1—C2—N2	−0.96 (9)	C7—C8—C9—C10	176.44 (7)
C4—N1—C2—N2	−171.57 (7)	C8—C9—C10—C11	0.31 (12)
C1—N1—C2—C6	−179.80 (7)	C9—C10—C11—C12	−0.59 (13)
C4—N1—C2—C6	9.60 (11)	C10—C11—C12—C13	0.33 (12)
C2—N2—C3—C7	−179.70 (8)	C14—O2—C13—C12	8.09 (11)
C2—N2—C3—C1	0.21 (8)	C14—O2—C13—C8	−171.68 (7)
O1—C1—C3—C7	−0.05 (13)	C11—C12—C13—O2	−179.54 (7)
N1—C1—C3—C7	179.18 (7)	C11—C12—C13—C8	0.22 (11)
O1—C1—C3—N2	−179.97 (9)	C9—C8—C13—O2	179.29 (7)
N1—C1—C3—N2	−0.74 (8)	C7—C8—C13—O2	2.86 (10)
C2—N1—C4—C5	94.61 (9)	C9—C8—C13—C12	−0.49 (11)
C1—N1—C4—C5	−74.77 (9)	C7—C8—C13—C12	−176.92 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···N2i	0.879 (16)	2.001 (16)	2.8771 (9)	174.2 (15)
C4—H4B···O1ii	0.99	2.54	3.2993 (10)	133
C9—H9···N2	0.95	2.52	3.1729 (10)	126
C14—H14A···O1iii	0.98	2.52	3.3475 (12)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯N2i	0.879 (16)	2.001 (16)	2.8771 (9)	174.2 (15)
C4—H4B⋯O1ii	0.99	2.54	3.2993 (10)	133
C9—H9⋯N2	0.95	2.52	3.1729 (10)	126
C14—H14A⋯O1iii	0.98	2.52	3.3475 (12)	141

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