(Z)-1-(2-Hy­droxy­eth­yl)-4-(2-meth­oxy­benzyl­idene)-2-methyl-1H-imidazol-5(4H)-one

Wu, H.; Wang, W.; Walker, E.H. Jr; Fronczek, F.R.

doi:10.1107/S1600536813007770

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o604-o605

doi:10.1107/S1600536813007770

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(Z)-1-(2-Hydroxyethyl)-4-(2-methoxybenzylidene)-2-methyl-1H-imidazol-5(4H)-one

Hongyi Wu,^a Weihua Wang,^a Edwin H. Walker Jr ^a and Frank R. Fronczek ^b ^*

^aDepartment of Chemistry, Southern University, Baton Rouge, LA 70813, USA, and ^bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
^*Correspondence e-mail: ffroncz@lsu.edu

(Received 8 March 2013; accepted 20 March 2013; online 28 March 2013)

In the title compound, C₁₄H₁₆N₂O₃, an analog of the chromophore in green fluorescent protein, the methoxyphenyl substituent and the imidazole N adopt a Z conformation with respect to the C=C bond. Aside from the hydroxyethyl group, the molecule is approximately planar, with the five- and six-membered ring planes forming a dihedral angle of 9.3 (1)°. An intramolecular C—H⋯N contact occurs. In the crystal, O—H⋯N hydrogen bonds link the molecules, 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_r = 260.29
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.087
S = 1.06
4943 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1605 Friedel pairs
Flack parameter: −0.9 (5)

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) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iii) x, y+1, z.

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813007770/sj5304sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813007770/sj5304Isup3.cml

checkCIF report

Comment top

The title compound is an analog of the chromophore in green fluorescent protein (GFP). GFP was first identified and separated from the jellyfish Aequorea victoria in the 1960s. Since then, GFP has found broad use in many areas of science and medicine, especially as fluorescent labels for cell biology and biotechnology. (Shimomura et al., 1962; Shimomura, 2009; Remington, 2006; Tsien, 1998; Chalfie et al., 1994) Though the GFP is a protein composed of more than two hundred amino acid residues, its chromophore (p-hydroxybenzylidene-imidazol-5-one) is relatively small. In nature, the GFP chromophore is formed via the sequential cyclization-oxidation-dehydration of the Ser⁶⁵—Tyr⁶⁶—Gly⁶⁷ tripeptide motif. (Prasher et al., 1992)

Preparation of the title compound starts with the Erlenmeyer azlactone synthesis, which involves the condensation of hippuric acid derivatives with aromatic aldehydes (Yampolsky et al., 2005; Bailly et al., 2004), Fig. 1. Further reaction of the resulting azlactone with ethanolamine leads to the formation of the title compound. We report the crystal structure of the compound here, which shows the compound has a Z-configuration. The compound is used as a model compound in our study of E, Z-isomerization of chromophores in fluorescent proteins.

The structure of the molecule is shown in Fig. 2. The Z configuration is evidenced by the torsion angle N2–C3–C7–C8 3.33 (14)° about the central double bond. The hydroxyethyl group is twisted away from coplanarity with the rest of the molecule (C1–N1–C4–C5 torsion angle -74.77 (9)°), but otherwise, the molecule is relatively planar, with the phenyl and imidazole rings forming a dihedral angle of 9.3 (1)°.

The OH group O3 forms a near-linear intermolecular hydrogen bond to the imidazole nitrogen atom N2 (at -x, y-1/2, 1-z), forming chains in the b direction, propagated by the screw axis. Several intermolecular C–H···O hydrogen bonds and an intramolecular C–H···N contact also exist, as given in Table 1.

Related literature top

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 top

A mixture of o-anisaldehyde (6.95 g, 50.0 mmol), N-acetylglycine (5.97 g, 50.5 mmol) and anhydrous sodium acetate (4.35 g, 52.5 mmol) were dissolved in 20 ml acetic anhydride. The mixture was stirred at 100° C for 6 h. Upon completion, the reaction mixture was cooled to room temperature. After the addition of 10 ml ice-cold water, the resulting precipitate was collected by gravity filtration. The filtrand was then washed three times with ice-cold water and dried in vacuum, yielding (1) as a yellow powder (8.41 g, 64.7%). Title compound (2) was synthesized by reacting (1) with ethanolamine in 2-propanol. To a suspension of compound (1) (3.30 g, 15.2 mmol) in dried 2-propanol (30 ml), ethanolamine (1.14 ml, 18.8 mmol) was added gradually. The reaction mixture was refluxed for 8 h. The solvent was then removed under vacuo. The crude product was recrystallized from a n-butanol/diethyl ether (1/1, v/v) mixture. Yellow crystals of the title compound (2) were obtained in a yield of 2.77 g (58%). The sample crystal was grown by evaporation from methanol.

FT—IR Characterization (cm^-1): 3237, 2944, 1711, 1635, 1423, 1256

NMR Characterization: ¹H NMR (400 MHz, CD₃Cl): δ 2.39 (s, 3 H, CH₃C), 3.74 (t, J = 5.9 Hz, 2H, CH₂), 3.81 (t, J=5.9 Hz, 2H, CH₂),3.89 (s, 3 H, CH₃O), 6.89 (m, 1 H, ArH), 7.02(m, 1 H, ArH), 7.35 (m, 1H, ArH), 7.67 (s, 1 H, HC═C), 8.68 (m, 1 H, ArH); ¹³C NMR (100 MHz, CD₃Cl): δ = 15.9(CH₃C), 43.7 (CH₂), 55.6(CH₃O), 62.0 (CH₂), 110.7 (ArCH), 120.9 (ArCH), 122.0 (HC═C),123.1 (ArCC), 131.8 (ArCH), 132.9 (ArCH), 137.7 (HC═C), 159.2(C—O), 162.3 (C═N), 171.3 (C═O).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).

Figures top

	Fig. 1. Scheme showing the synthesis.
	Fig. 2. Ellipsoids at the 50% level, with H atoms having arbitrary radius.

(Z)-1-(2-Hydroxyethyl)-4-(2-methoxybenzylidene)-2-methyl-1H-imidazol-5(4H)-one top

Crystal data top

C₁₄H₁₆N₂O₃	F(000) = 276
M_r = 260.29	D_x = 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

Data collection top

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	R_int = 0.017
ϕ and ω scans	θ_max = 37.8°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→13
T_min = 0.967, T_max = 0.984	k = −8→12
9385 measured reflections	l = −15→15

Refinement top

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(F_o²) + (0.0603P)² + 0.0209P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4943 reflections	Δρ_max = 0.42 e Å⁻³
177 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1605 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.9 (5)

Crystal data top

C₁₄H₁₆N₂O₃	V = 640.16 (6) Å³
M_r = 260.29	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.2188 (5) Å	µ = 0.10 mm⁻¹
b = 7.2767 (4) Å	T = 90 K
c = 9.5620 (5) Å	0.35 × 0.25 × 0.17 mm
β = 93.625 (6)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	4943 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4720 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.984	R_int = 0.017
9385 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	Δρ_max = 0.42 e Å⁻³
S = 1.06	Δρ_min = −0.24 e Å⁻³
4943 reflections	Absolute structure: Flack (1983), 1605 Friedel pairs
177 parameters	Absolute structure parameter: −0.9 (5)
1 restraint

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	0.46857 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₂O₃
M_r	260.29
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	90
a, b, c (Å)	9.2188 (5), 7.2767 (4), 9.5620 (5)
β (°)	93.625 (6)
V (Å³)	640.16 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.25 × 0.17

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.967, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9385, 4943, 4720
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.862

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.087, 1.06
No. of reflections	4943
No. of parameters	177
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.24
Absolute structure	Flack (1983), 1605 Friedel pairs
Absolute structure parameter	−0.9 (5)

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) x, y+1, z.

Acknowledgements

This research was made possible by a grant supplied by the National Science Foundation's Early CAREER program (Cooperative Agreement DMR-0449886)and by the National Science Foundations HBCU–RISE program (Cooperative Agreement HRD-1036588) at Southern University. The purchase of the NMR was made possible by the National Science Foundation's Major Research Instrument program (Cooperative Agreement CHE-0321591) at Southern University. The purchase of the FTIR at Southern University was made possible by the support from Louisiana Board of Regents (grant No. LEQSF(2005–2007)-ENH-TR-65). We also want to thank the US Department of Education: Title III Part B HBGI program (grant No. P031B040030) at Southern University. Upgrade of the diffractometer at LSU was made possible by grant No. LEQSF(2011–12)-ENH-TR-01, administered by the Louisiana Board of Regents.

References

Bailly, F., Maurin, C., Teissier, E., Vezin, H. & Cotelle, P. (2004). Bioorg. Med. Chem. 12, 5611–5618. Web of Science CrossRef PubMed CAS Google Scholar
Bhattacharjya, G., Govardhan, S. & Ramanathan, G. (2005). J. Mol. Struct. 752, 98–103. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chalfie, M., Tu, Y., Euskirchen, G., Ward, W. W. & Prasher, D. C. (1994). Science, 263, 802–805. CrossRef CAS PubMed Web of Science Google Scholar
Dong, J., Solntsev, K. M. & Tolbert, L. M. (2009). J. Am. Chem. Soc. 131, 662–670. Web of Science CSD CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96–103. Web of Science CrossRef CAS IUCr Journals Google Scholar
Naumov, P., Kowalik, J., Solntsev, K. M., Baldridge, A., Moon, J.-S., Kranz, C. & Tolbert, L. M. (2010). J. Am. Chem. Soc. 132, 5845–5857. Web of Science CSD CrossRef CAS PubMed Google Scholar
Oshimi, K., Kubo, K., Kawasaki, A., Maekawa, K., Igarashi, T. & Sakurai, T. (2002). Tetrahedron Lett. 43, 3291–3294. Web of Science CSD CrossRef CAS Google Scholar
Prasher, D. C., Eckenrode, V. K., Ward, W. W., Prendergast, F. G. & Cormier, M. J. (1992). Gene, 111, 229–233. CrossRef PubMed CAS Web of Science Google Scholar
Remington, S. J. (2006). Curr. Opin. Struct. Biol. 16, 714–721. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shimomura, O. (2009). Angew. Chem. Int. Ed. Engl. 48, 5590–5602. Web of Science CrossRef PubMed CAS Google Scholar
Shimomura, O., Johnson, F. H. & Saiga, Y. (1962). J. Cell. Comp. Physiol. 59, 223–239. CrossRef PubMed CAS Web of Science Google Scholar
Tsien, R. Y. (1998). Annu. Rev. Biochem. 67, 509–544. Web of Science CrossRef CAS PubMed Google Scholar
Wenge, U. & Wagenknecht, H.-A. (2011). Synthesis, 3, 0502–0508. Google Scholar
Yampolsky, I. V., Remington, S. J., Martynov, V. I., Potapov, V. K., Lukyanov, S. & Lukyanov, K. A. (2005). Biochemistry, 44, 5788–5793. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 69| Part 4| April 2013| Pages o604-o605

doi:10.1107/S1600536813007770

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

(Z)-1-(2-Hy­dr­oxy­eth­yl)-4-(2-meth­­oxy­benzyl­­idene)-2-methyl-1H-imidazol-5(4H)-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-1-(2-Hydroxyethyl)-4-(2-methoxybenzylidene)-2-methyl-1H-imidazol-5(4H)-one