Zwitterionic 6-methyl-2-oxo-3-[1-(ureido­iminio)eth­yl]-2H-pyran-4-olate monohydrate

Djedouani, A.; Boufas, S.; Allain, M.; Bouet, G.; Khan, M.

doi:10.1107/S1600536808026032

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1785

doi:10.1107/S1600536808026032

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Zwitterionic 6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2H-pyran-4-olate monohydrate

Amel Djedouani,^a Sihem Boufas,^b ^* Magali Allain,^c Gilles Bouet ^d and Mustayeen Khan ^d

^aLaboratoire d'Electrochimie des Matériaux Moléculaires et Complexes, Département de Génie des Procédés, Faculté des Science de l'Ingénieur, Université Farhet Abbes de Setif, DZ-19000 Sétif, Algeria, ^bUniversité 20 Aout 1955, Skikda, Algeria, ^cCIMM, CNRS UMR 6200, Faculté des Science, Angers Cedex, France, and ^dSONAS, EA 921, Université D'Angers, Faculté de Pharmacie, Angers Cedex, France
^*Correspondence e-mail: boufas_sihem@yahoo.fr

(Received 5 August 2008; accepted 12 August 2008; online 20 August 2008)

The title compound, C₉H₁₁N₃O₄·H₂O, was prepared by the reaction of dehydroacetic acid and semicarbazide hydrochloride. It crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. In the crystal structure, the almost planar molecules are held together by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, some of them involving the water molecules.

Related literature

For related literature, see: Tai et al. (2007 ); Zu-Pei Liang et al. (2007 ); Wojciechowski et al. (2003 ); Petek et al. (2006 ); Huang et al. (2006 ); Bernstein et al. (1995 ); Girija & Begum (2004a ); Girija et al. (2004b ); Gowda et al. (2007 )..

Experimental

Crystal data

C₉H₁₁N₃O₄·H₂O
M_r = 243.22
Monoclinic, P 2₁ /c
a = 7.1731 (4) Å
b = 12.6590 (10) Å
c = 12.3698 (3) Å
β = 104.603 (6)°
V = 1086.95 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 173 (2) K
0.35 × 0.05 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
11787 measured reflections
2485 independent reflections
1699 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.121
S = 1.03
2485 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.84 (2)	2.18 (2)	3.015 (2)	176.3 (17)
N1—H1B⋯O1Wⁱⁱ	0.87 (2)	2.30 (2)	3.075 (2)	147.9 (19)
N2—H2⋯O1Wⁱⁱ	0.91 (2)	1.98 (2)	2.839 (2)	158 (2)
N3—H3⋯O3	0.98 (2)	1.60 (3)	2.476 (2)	147 (2)
O1W—H11W⋯O4	0.82 (3)	1.99 (3)	2.796 (2)	171 (3)
O1W—H21W⋯O1ⁱⁱⁱ	0.82 (3)	2.00 (3)	2.823 (2)	178.0 (18)
C3—H3B⋯O1	0.96	2.29	2.812 (3)	114
C7—H7⋯O4^iv	0.93	2.49	3.294 (2)	145
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+1; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1997 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026032/wk2091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026032/wk2091Isup2.hkl

checkCIF report

Comment top

NLO materials play an important role in the field of fibre optic communications and optical signal processing. In the last two decades, extensive research has shown that organic crystals can exhibit nonlinear optical efficiencies which are two orders of magnitude higher than those of inorganic materials. Semicarbazones of substituted benzaldehydes and acetophenones were reported to be some of the potential organic NLO materials.

In this paper, the structure of the title compound (I), C₉H₁₃N₃O₅ is reported. The asymmetric unit of (I) contains one Dehydroacetic acid semicarbazide molecule and one water molecule (Fig. 1).

It is seen that the structure reported here adopts a zwitterion form, because, among other reasons, its N⁺—H bond distances [0.98 (3) Å] is comparable with those from similar zwitterions in the literature [1.11 (3) Å; 1.10 (3) Å] (Petek et al., 2006; Wojciechowski et al., 2003).

The bond distances shown in Table 1 indicate that the C2—N3 iminium bond length of 1.303 (2) Å agree with similar bond in related compounds (Girija & Begum, 2004a; Girija et al., 2004b). This distance is slightly longer than a typical C=N bond (1.269 Å); but much shorter than the single carbon-nitrogen (1.409 Å) (Gowda et al. 2007), because of the resonance.

The C8—O3 bond length [1.282 (2) Å] is intermediate between single and double carbon to oxygen bond lengths (1.362 Å, 1.222 Å) the carbon-carbon bond connecting the enol and imine groups exhibit intermediate distances between a single and a double bond, being closer to latter one. C4—C8 = 1.423 (2) Å, C2—C4 = 1.452 (2) Å, indicate the zwitterionic character of the title compound (Wojciechowski et al. 2003). The molecular configuration is determined by the presence of the intramolecular hydrogen bond O^-···H—N⁺ (Table 2).

The main molecule in (I) is essentially planar, with a maximum deviation from the mean plane for the non-hydrogen atoms of 0.022 (2) Å. The iminium atom H3, participates in a strong intramolecular hydrogen bond with the enolate atom, O1 (Table 1), which generates an S(6) ring motif (Bernstein et al. 1995). Similar intramolecular hydrogen bonds were reported in the above-mentioned zwitterionic phenolates (Huang et al. 2006). This six-membered pseudocycle is almost planar, the maximum deviation from the mean plane being 0.012 Å for atom C2. The bond lengths and angles are in usual ranges (E)-1-(4-Hydroxybenzylidene) semicarbazide hemihydrate (Tai et al., 2007) and (E)-1-(4-Methoxybenzylidene) -semicarbazide (Liang et al., 2007).

The crystal structure of (I) is stabilized by N—H···O; O—H···O, and C—H···O hydrogen bonds (Fig. 2 and Table 2).

Related literature top

For related literature, see: Tai et al. (2007); Zu-Pei Liang et al. (2007); Wojciechowski et al. (2003); Petek et al. (2006); Huang et al. (2006); Bernstein et al. (1995); Girija & Begum (2004a); Girija et al. (2004b); Gowda et al. (2007).

Experimental top

A mixture of dehydroacetic acid (0.01 mol) and semicarbazide hydrochloride (0.01 mol), in ethanol (20 ml) was refluxed for 1 h. After cooling, filtration and drying, the compound dehydroacetic acid semicarbazide was obtained. A small quantity of this compound (10 mg) was dissolved in aqueous ethanol (95 / 12 ml), and the solution was then allowed to evaporate at room temperature. Prismatic yellow single crystals of the title compound were formed after 8 days.

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I), viewed down the b axis. Dashed lines indicate the N—H···O and O—H···O interactions.

6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2H-pyran-4-olate monohydrate top

Crystal data top

C₉H₁₁N₃O₄·H₂O	F(000) = 512
M_r = 243.22	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2841 reflections
a = 7.1731 (4) Å	θ = 3.1–25.8°
b = 12.659 (1) Å	µ = 0.12 mm⁻¹
c = 12.3698 (3) Å	T = 173 K
β = 104.603 (6)°	Prism, yellow
V = 1086.95 (11) Å³	0.35 × 0.05 × 0.02 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	1699 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
CCD scans	h = −9→9
11787 measured reflections	k = −16→15
2485 independent reflections	l = −15→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0289P)² + 0.445P] where P = (F_o² + 2F_c²)/3
2485 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₉H₁₁N₃O₄·H₂O	V = 1086.95 (11) Å³
M_r = 243.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1731 (4) Å	µ = 0.12 mm⁻¹
b = 12.659 (1) Å	T = 173 K
c = 12.3698 (3) Å	0.35 × 0.05 × 0.02 mm
β = 104.603 (6)°

Data collection top

Nonius KappaCCD diffractometer	1699 reflections with I > 2σ(I)
11787 measured reflections	R_int = 0.055
2485 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
2485 reflections	Δρ_min = −0.26 e Å⁻³
178 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5343 (3)	−0.25527 (15)	0.37044 (14)	0.0287 (4)
C2	0.7633 (2)	−0.06094 (14)	0.56842 (14)	0.0253 (4)
C3	0.8032 (4)	−0.11552 (17)	0.67854 (16)	0.0476 (6)
H3A	0.7151	−0.1734	0.6744	0.057*
H3B	0.7871	−0.0666	0.7348	0.057*
H3C	0.9329	−0.1418	0.6974	0.057*
C4	0.8087 (2)	0.04894 (13)	0.55327 (13)	0.0240 (4)
C5	0.9088 (3)	0.11044 (14)	0.64744 (15)	0.0292 (4)
C6	0.8929 (3)	0.26084 (15)	0.52451 (15)	0.0305 (4)
C7	0.8054 (3)	0.20520 (15)	0.43545 (15)	0.0316 (4)
H7	0.7733	0.2375	0.3657	0.038*
C8	0.7593 (2)	0.09564 (14)	0.44518 (14)	0.0269 (4)
C9	0.9441 (3)	0.37503 (16)	0.52619 (18)	0.0422 (5)
H9A	0.9024	0.4034	0.452	0.051*
H9B	1.0812	0.3829	0.5527	0.051*
H9C	0.8817	0.4123	0.5749	0.051*
N1	0.4877 (3)	−0.35801 (14)	0.36960 (16)	0.0397 (4)
N2	0.6282 (2)	−0.21693 (12)	0.47382 (13)	0.0336 (4)
N3	0.6811 (2)	−0.11234 (12)	0.47752 (12)	0.0272 (3)
O1	0.9689 (2)	0.08309 (11)	0.74427 (10)	0.0424 (4)
O3	0.6744 (2)	0.04451 (10)	0.35702 (10)	0.0369 (4)
O2	0.9464 (2)	0.21590 (10)	0.62831 (10)	0.0355 (3)
O4	0.4983 (2)	−0.19779 (11)	0.28793 (11)	0.0414 (4)
O1W	0.6521 (3)	−0.10956 (13)	0.12207 (12)	0.0470 (4)
H11W	0.597 (4)	−0.131 (2)	0.168 (2)	0.071*
H21W	0.763 (4)	−0.103 (2)	0.160 (2)	0.071*
H1A	0.440 (3)	−0.3872 (19)	0.308 (2)	0.048 (7)*
H1B	0.514 (3)	−0.3924 (17)	0.4326 (19)	0.037 (6)*
H2	0.650 (3)	−0.2591 (18)	0.5351 (19)	0.042 (6)*
H3	0.656 (4)	−0.069 (2)	0.410 (2)	0.075 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0301 (9)	0.0304 (10)	0.0238 (8)	−0.0033 (7)	0.0036 (7)	−0.0023 (7)
C2	0.0258 (9)	0.0274 (9)	0.0222 (8)	0.0011 (7)	0.0049 (7)	0.0004 (7)
C3	0.0780 (16)	0.0371 (12)	0.0232 (10)	−0.0137 (11)	0.0043 (10)	0.0025 (8)
C4	0.0260 (9)	0.0241 (9)	0.0203 (8)	0.0006 (7)	0.0028 (7)	−0.0015 (6)
C5	0.0318 (10)	0.0288 (10)	0.0254 (9)	−0.0014 (8)	0.0042 (7)	−0.0023 (7)
C6	0.0341 (10)	0.0264 (9)	0.0306 (9)	−0.0012 (7)	0.0073 (8)	0.0002 (7)
C7	0.0379 (11)	0.0283 (10)	0.0256 (9)	0.0005 (8)	0.0023 (8)	0.0046 (7)
C8	0.0283 (9)	0.0260 (9)	0.0237 (9)	0.0027 (7)	0.0016 (7)	−0.0001 (7)
C9	0.0557 (13)	0.0270 (10)	0.0417 (12)	−0.0078 (9)	0.0082 (10)	−0.0023 (8)
N1	0.0568 (12)	0.0304 (9)	0.0295 (9)	−0.0110 (8)	0.0063 (8)	−0.0035 (8)
N2	0.0488 (10)	0.0240 (8)	0.0243 (8)	−0.0078 (7)	0.0023 (7)	0.0014 (6)
N3	0.0330 (8)	0.0230 (8)	0.0225 (7)	−0.0021 (6)	0.0016 (6)	0.0002 (6)
O1	0.0586 (9)	0.0412 (8)	0.0201 (6)	−0.0112 (7)	−0.0036 (6)	0.0005 (6)
O3	0.0539 (9)	0.0288 (7)	0.0204 (6)	−0.0043 (6)	−0.0046 (6)	0.0014 (5)
O2	0.0480 (8)	0.0284 (7)	0.0264 (7)	−0.0085 (6)	0.0024 (6)	−0.0033 (5)
O4	0.0562 (9)	0.0366 (8)	0.0248 (7)	−0.0108 (7)	−0.0018 (6)	0.0027 (6)
O1W	0.0593 (10)	0.0501 (10)	0.0294 (8)	−0.0083 (8)	0.0068 (7)	−0.0032 (7)

Geometric parameters (Å, º) top

C1—O4	1.227 (2)	C6—C9	1.490 (3)
C1—N1	1.342 (2)	C7—C8	1.438 (3)
C1—N2	1.375 (2)	C7—H7	0.93
C2—N3	1.304 (2)	C8—O3	1.282 (2)
C2—C4	1.452 (2)	C9—H9A	0.96
C2—C3	1.489 (2)	C9—H9B	0.96
C3—H3A	0.96	C9—H9C	0.96
C3—H3B	0.96	N1—H1A	0.84 (3)
C3—H3C	0.96	N1—H1B	0.87 (2)
C4—C8	1.423 (2)	N2—N3	1.375 (2)
C4—C5	1.434 (2)	N2—H2	0.91 (2)
C5—O1	1.217 (2)	N3—H3	0.98 (3)
C5—O2	1.394 (2)	O1W—H11W	0.82 (3)
C6—C7	1.325 (3)	O1W—H21W	0.82 (3)
C6—O2	1.368 (2)

O4—C1—N1	124.65 (17)	C6—C7—H7	119.5
O4—C1—N2	121.02 (17)	C8—C7—H7	119.5
N1—C1—N2	114.33 (16)	O3—C8—C4	122.81 (16)
N3—C2—C4	115.73 (15)	O3—C8—C7	119.05 (15)
N3—C2—C3	119.87 (17)	C4—C8—C7	118.13 (15)
C4—C2—C3	124.41 (16)	C6—C9—H9A	109.5
C2—C3—H3A	109.5	C6—C9—H9B	109.5
C2—C3—H3B	109.5	H9A—C9—H9B	109.5
H3A—C3—H3B	109.5	C6—C9—H9C	109.5
C2—C3—H3C	109.5	H9A—C9—H9C	109.5
H3A—C3—H3C	109.5	H9B—C9—H9C	109.5
H3B—C3—H3C	109.5	C1—N1—H1A	118.7 (16)
C8—C4—C5	119.53 (16)	C1—N1—H1B	118.7 (14)
C8—C4—C2	120.58 (15)	H1A—N1—H1B	122 (2)
C5—C4—C2	119.87 (15)	N3—N2—C1	115.93 (15)
O1—C5—O2	113.83 (16)	N3—N2—H2	123.4 (14)
O1—C5—C4	128.74 (18)	C1—N2—H2	120.7 (14)
O2—C5—C4	117.43 (15)	C2—N3—N2	124.75 (15)
C7—C6—O2	121.43 (17)	C2—N3—H3	113.8 (17)
C7—C6—C9	126.21 (18)	N2—N3—H3	121.4 (17)
O2—C6—C9	112.36 (16)	C6—O2—C5	122.49 (14)
C6—C7—C8	120.93 (17)	H11W—O1W—H21W	102 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.84 (2)	2.18 (2)	3.015 (2)	176.3 (17)
N1—H1B···O1Wⁱⁱ	0.87 (2)	2.30 (2)	3.075 (2)	147.9 (19)
N2—H2···O1Wⁱⁱ	0.91 (2)	1.98 (2)	2.839 (2)	158 (2)
N3—H3···O3	0.98 (2)	1.60 (3)	2.476 (2)	147 (2)
O1W—H11W···O4	0.82 (3)	1.99 (3)	2.796 (2)	171 (3)
O1W—H21W···O1ⁱⁱⁱ	0.82 (3)	2.00 (3)	2.823 (2)	178 (2)
C3—H3B···O1	0.96	2.29	2.812 (3)	114
C7—H7···O4^iv	0.93	2.49	3.294 (2)	145

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

Experimental details

Crystal data
Chemical formula	C₉H₁₁N₃O₄·H₂O
M_r	243.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.1731 (4), 12.659 (1), 12.3698 (3)
β (°)	104.603 (6)
V (Å³)	1086.95 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.35 × 0.05 × 0.02

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11787, 2485, 1699
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.121, 1.03
No. of reflections	2485
No. of parameters	178
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.26

Computer programs: COLLECT (Nonius, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

Selected bond lengths (Å) top

C2—N3	1.304 (2)	C4—C8	1.423 (2)
C2—C4	1.452 (2)	C8—O3	1.282 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.84 (2)	2.18 (2)	3.015 (2)	176.3 (17)
N1—H1B···O1Wⁱⁱ	0.87 (2)	2.30 (2)	3.075 (2)	147.9 (19)
N2—H2···O1Wⁱⁱ	0.91 (2)	1.98 (2)	2.839 (2)	158 (2)
N3—H3···O3	0.98 (2)	1.60 (3)	2.476 (2)	147 (2)
O1W—H11W···O4	0.82 (3)	1.99 (3)	2.796 (2)	171 (3)
O1W—H21W···O1ⁱⁱⁱ	0.82 (3)	2.00 (3)	2.823 (2)	178.0 (18)
C3—H3B···O1	0.9600	2.2900	2.812 (3)	114.00
C7—H7···O4^iv	0.9300	2.4900	3.294 (2)	145.00

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

Acknowledgements

This work was supported by Université Farhet Abbes de Sétif, Sétif, Algeria.

References

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Volume 64| Part 9| September 2008| Page o1785

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

Zwitterionic 6-methyl-2-oxo-3-[1-(ureido­iminio)eth­yl]-2H-pyran-4-olate monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Zwitterionic 6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2H-pyran-4-olate monohydrate